# Electronic Supplementary Material (ESI) for RSC Advances. # This journal is © The Royal Society of Chemistry 2020 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_c17058 _database_code_depnum_ccdc_archive 'CCDC 1998517' loop_ _audit_author_name _audit_author_address 'Sean Parkin' ;UKy United States of America ; # CIF edited on-the-fly by script CIFFIX (S. Parkin, 2000-2017). # CIFFIX: http://xray.uky.edu/people/parkin/programs/ciffix _audit_update_record ; 2020-04-22 deposited with the CCDC. 2020-06-16 downloaded from the CCDC. ; _audit_creation_method 'SHELXL-2017 and CIFFIX/1' _shelx_SHELXL_version_number 2017/1 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C28 H28 N2 O6) C H2 Cl2' _chemical_formula_sum 'C57 H58 Cl2 N4 O12' _chemical_formula_weight 1061.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_H-M_alt 'C 2' _space_group_name_Hall 'C 2y' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.791(2) _cell_length_b 6.7169(6) _cell_length_c 17.0032(16) _cell_angle_alpha 90 _cell_angle_beta 103.374(4) _cell_angle_gamma 90 _cell_volume 2643.5(4) _cell_formula_units_Z 2 _cell_measurement_temperature 90.0(2) _cell_measurement_reflns_used 9842 _cell_measurement_theta_min 3.82 _cell_measurement_theta_max 74.59 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_F_000 1116 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.020 _exptl_absorpt_coefficient_mu 1.663 _shelx_estimated_absorpt_T_min 0.635 _shelx_estimated_absorpt_T_max 0.967 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.760 _exptl_absorpt_correction_T_max 0.929 _exptl_absorpt_process_details 'SADABS (Krause et al., 2015)' _exptl_absorpt_special_details ; In addition to absorption, multi-scan techniques also correct other slowly varying changes in scale factor over reciprocal space, such as those caused by x-ray beam inhomogeneity, goniometer imperfection, crystal decomposition, crystal longer than the x-ray beam cross section, absorption by the crystal mount etc. These account, by and large, for much of the difference between estimated values of Tmin and Tmax and the _exptl_absorpt_correction_ values. ; _exptl_special_details ; The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998). Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals. ; _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_source microsource _diffrn_measurement_device_type 'Bruker D8 Venture dual source' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 5.6 _diffrn_reflns_number 25456 _diffrn_reflns_av_unetI/netI 0.0541 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.671 _diffrn_reflns_theta_max 74.520 _diffrn_reflns_theta_full 67.679 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_Laue_measured_fraction_max 0.976 _diffrn_reflns_Laue_measured_fraction_full 0.976 _diffrn_reflns_point_group_measured_fraction_max 0.968 _diffrn_reflns_point_group_measured_fraction_full 0.973 _reflns_number_total 5266 _reflns_number_gt 4832 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.823 _reflns_Friedel_fraction_max 0.959 _reflns_Friedel_fraction_full 0.969 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX3 (Bruker-AXS, 2016)' _computing_cell_refinement 'APEX3 (Bruker-AXS, 2016)' _computing_data_reduction 'APEX3 (Bruker-AXS, 2016)' _computing_structure_solution 'SHELXT (Sheldrick, 2015a)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2015b)' _computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)' _refine_special_details ; Refinement progress was checked using Platon (Spek, 2009) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+1.4710P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Flack 'x' determined using 2011 quotients [(I+)-(I-)]/[(I+)+(I-)] [Parsons, Flack and Wagner (2013)]. ; _refine_ls_abs_structure_Flack 0.068(14) _chemical_absolute_configuration ad # Might have been a tiny amount of an inverted twin component. _refine_ls_number_reflns 5266 _refine_ls_number_parameters 367 _refine_ls_number_restraints 86 _refine_ls_R_factor_all 0.0427 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.24018(8) 0.7694(5) 0.68077(12) 0.0230(4) Uani 1 1 d . . . . . N2 N 0.42556(9) 0.5283(5) 0.66969(12) 0.0224(5) Uani 1 1 d . . . . . H2 H 0.399931 0.431529 0.662616 0.027 Uiso 1 1 calc R U . . . O1 O 0.35387(10) 0.4930(5) 0.51625(12) 0.0383(5) Uani 1 1 d . . . . . O2 O 0.38716(7) 0.7856(5) 0.48027(10) 0.0258(4) Uani 1 1 d . . . . . O3 O 0.17681(7) 0.7960(4) 0.32539(11) 0.0266(4) Uani 1 1 d . . . . . O4 O 0.29830(8) 0.7431(5) 0.09829(11) 0.0351(5) Uani 1 1 d . . . . . O5 O 0.51199(8) 0.6427(5) 0.74113(11) 0.0280(4) Uani 1 1 d . . . . . O6 O 0.47311(7) 0.3523(4) 0.77435(11) 0.0265(4) Uani 1 1 d . . . . . C1 C 0.27142(10) 0.7590(5) 0.75936(14) 0.0223(5) Uani 1 1 d . . . . . C2 C 0.25243(11) 0.7379(5) 0.83086(15) 0.0247(5) Uani 1 1 d . . . . . H2A H 0.212521 0.725660 0.830069 0.030 Uiso 1 1 calc R U . . . C3 C 0.29393(12) 0.7355(5) 0.90268(15) 0.0274(6) Uani 1 1 d . . . . . H3 H 0.282436 0.720982 0.952288 0.033 Uiso 1 1 calc R U . . . C4 C 0.35304(12) 0.7541(6) 0.90347(15) 0.0283(6) Uani 1 1 d . . . . . H4 H 0.380729 0.751002 0.953659 0.034 Uiso 1 1 calc R U . . . C5 C 0.37154(11) 0.7769(6) 0.83278(15) 0.0253(5) Uani 1 1 d . . . . . H5 H 0.411570 0.787256 0.834113 0.030 Uiso 1 1 calc R U . . . C6 C 0.33051(10) 0.7844(5) 0.75917(14) 0.0224(5) Uani 1 1 d . . . . . C7 C 0.33317(11) 0.8204(5) 0.67692(15) 0.0221(5) Uani 1 1 d . . . . . C8 C 0.27752(11) 0.8095(5) 0.63192(15) 0.0235(5) Uani 1 1 d . . . . . H8 H 0.266278 0.827091 0.574994 0.028 Uiso 1 1 calc R U . . . C9 C 0.17741(10) 0.7597(6) 0.65606(16) 0.0265(5) Uani 1 1 d . . . . . H9A H 0.165526 0.746310 0.597145 0.040 Uiso 1 1 calc R U . . . H9B H 0.160844 0.881750 0.672800 0.040 Uiso 1 1 calc R U . . . H9C H 0.163632 0.644528 0.681592 0.040 Uiso 1 1 calc R U . . . C10 C 0.38672(11) 0.8755(5) 0.64940(15) 0.0245(6) Uani 1 1 d . . . . . H10A H 0.414677 0.936564 0.695342 0.029 Uiso 1 1 calc R U . . . H10B H 0.376510 0.977402 0.606377 0.029 Uiso 1 1 calc R U . . . C11 C 0.41652(10) 0.6989(5) 0.61685(14) 0.0217(5) Uani 1 1 d . . . . . H11 H 0.455256 0.745700 0.611046 0.026 Uiso 1 1 calc R U . . . C12 C 0.38219(10) 0.6391(5) 0.53398(15) 0.0225(5) Uani 1 1 d . . . . . C13 C 0.35676(10) 0.7672(5) 0.39981(14) 0.0220(5) Uani 1 1 d . . . . . C14 C 0.29682(10) 0.7719(5) 0.37897(14) 0.0221(5) Uani 1 1 d . . . . . H14 H 0.275250 0.778157 0.419454 0.027 Uiso 1 1 calc R U . . . C15 C 0.26913(10) 0.7671(5) 0.29766(14) 0.0200(5) Uani 1 1 d . . . . . C16 C 0.2046(1) 0.7774(5) 0.27350(14) 0.0214(5) Uani 1 1 d . . . . . C17 C 0.17703(10) 0.7656(5) 0.18727(15) 0.0244(5) Uani 1 1 d . . . . . H17 H 0.136027 0.768275 0.171659 0.029 Uiso 1 1 calc R U . . . C18 C 0.20645(11) 0.7513(5) 0.12900(14) 0.0243(5) Uani 1 1 d . . . . . C19 C 0.17823(12) 0.7390(6) 0.04066(15) 0.0303(6) Uani 1 1 d . . . . . H19A H 0.188430 0.856919 0.012988 0.046 Uiso 1 1 calc R U . . . H19B H 0.136198 0.732962 0.033570 0.046 Uiso 1 1 calc R U . . . H19C H 0.191614 0.619097 0.017674 0.046 Uiso 1 1 calc R U . . . C20 C 0.27096(11) 0.7500(6) 0.15053(14) 0.0245(5) Uani 1 1 d . . . . . C21 C 0.3008(1) 0.7578(5) 0.23772(14) 0.0211(5) Uani 1 1 d . . . . . C22 C 0.36113(10) 0.7561(5) 0.26061(14) 0.0228(5) Uani 1 1 d . . . . . H22 H 0.382998 0.751773 0.220440 0.027 Uiso 1 1 calc R U . . . C23 C 0.38907(10) 0.7608(5) 0.34140(14) 0.0231(5) Uani 1 1 d . . . . . H23 H 0.430080 0.759547 0.356939 0.028 Uiso 1 1 calc R U . . . C24 C 0.4734(1) 0.5178(6) 0.72986(15) 0.0225(5) Uani 1 1 d . . . . . C25 C 0.52223(11) 0.3092(6) 0.84310(15) 0.0257(6) Uani 1 1 d . . . . . C26 C 0.57632(11) 0.2711(6) 0.81269(17) 0.0321(6) Uani 1 1 d . . . . . H26A H 0.568935 0.164253 0.772375 0.048 Uiso 1 1 calc R U . . . H26B H 0.607868 0.231731 0.858045 0.048 Uiso 1 1 calc R U . . . H26C H 0.587127 0.392791 0.787983 0.048 Uiso 1 1 calc R U . . . C27 C 0.52963(14) 0.4775(6) 0.90477(17) 0.0364(7) Uani 1 1 d . . . . . H27A H 0.544970 0.595461 0.882979 0.055 Uiso 1 1 calc R U . . . H27B H 0.556566 0.435831 0.954796 0.055 Uiso 1 1 calc R U . . . H27C H 0.492124 0.509547 0.916191 0.055 Uiso 1 1 calc R U . . . C28 C 0.50350(13) 0.1193(6) 0.87751(19) 0.0375(7) Uani 1 1 d . . . . . H28A H 0.496984 0.015387 0.835939 0.056 Uiso 1 1 calc R U . . . H28B H 0.467636 0.143429 0.895025 0.056 Uiso 1 1 calc R U . . . H28C H 0.533738 0.076158 0.923853 0.056 Uiso 1 1 calc R U . . . C1S C 0.4803(4) 0.1769(14) 0.5129(3) 0.0437(19) Uani 0.399(4) 1 d D U P A -1 H1S1 H 0.441092 0.199348 0.521617 0.052 Uiso 0.399(4) 1 calc R U P A -1 H1S2 H 0.492948 0.041716 0.532600 0.052 Uiso 0.399(4) 1 calc R U P A -1 Cl1S Cl 0.5282(4) 0.3549(16) 0.5674(3) 0.0822(19) Uani 0.399(4) 1 d D U P A -1 Cl2S Cl 0.47873(17) 0.1950(6) 0.40917(16) 0.0624(10) Uani 0.399(4) 1 d D U P A -1 C1S' C 0.504(2) 0.459(3) 0.5088(13) 0.0437(19) Uani 0.101(4) 1 d D U P A -2 H1S3 H 0.478374 0.554338 0.527792 0.052 Uiso 0.101(4) 1 calc R U P A -2 H1S4 H 0.537178 0.534493 0.497568 0.052 Uiso 0.101(4) 1 calc R U P A -2 Cl1' Cl 0.5295(15) 0.280(4) 0.5844(11) 0.0822(19) Uani 0.101(4) 1 d D U P A -2 Cl2' Cl 0.4662(11) 0.341(4) 0.420(1) 0.0624(10) Uani 0.101(4) 1 d D U P A -2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0215(10) 0.0235(11) 0.0244(9) 0.0012(10) 0.0061(7) 0.0005(9) N2 0.0189(10) 0.0257(12) 0.022(1) 0.0032(9) 0.0039(8) -0.0027(9) O1 0.0539(13) 0.0341(13) 0.0237(9) 0.0025(9) 0.0027(9) -0.0141(11) O2 0.0279(9) 0.0268(10) 0.0212(8) 0.0036(8) 0.0024(6) -0.0030(8) O3 0.0231(8) 0.0274(11) 0.0313(9) 0.0037(8) 0.0102(7) 0.0047(8) O4 0.0328(10) 0.0507(14) 0.0229(8) -0.0004(10) 0.0089(7) 0.0028(10) O5 0.0208(8) 0.0325(11) 0.0298(9) 0.0051(8) 0.0038(7) -0.0062(8) O6 0.0203(8) 0.0324(11) 0.0250(8) 0.0074(8) 0.0015(7) -0.0035(8) C1 0.0247(12) 0.0187(12) 0.0244(11) -0.0006(11) 0.0078(9) 0.0003(11) C2 0.0294(12) 0.0194(13) 0.0285(12) -0.0011(11) 0.0133(10) -0.0002(11) C3 0.0379(14) 0.0229(14) 0.0242(11) -0.0002(11) 0.0126(10) 0.0019(12) C4 0.0339(13) 0.0258(14) 0.0236(11) -0.0007(12) 0.0037(10) 0.0011(12) C5 0.0275(12) 0.0227(13) 0.0259(11) -0.0015(11) 0.0063(9) -0.0014(11) C6 0.0242(11) 0.0184(13) 0.0256(11) -0.0010(11) 0.0077(9) -0.0023(10) C7 0.0252(12) 0.0182(12) 0.0240(11) 0.0002(10) 0.0082(9) 0.0006(10) C8 0.0287(12) 0.0208(13) 0.0218(11) -0.0003(10) 0.0076(9) 0.0014(10) C9 0.0226(11) 0.0249(14) 0.0317(12) 0.0015(12) 0.0056(9) 0.0019(11) C10 0.0272(13) 0.0250(14) 0.0223(11) 0.0004(11) 0.0077(10) -0.0040(11) C11 0.018(1) 0.0263(14) 0.0213(11) 0.0035(10) 0.0059(9) -0.0019(10) C12 0.0226(11) 0.0243(14) 0.0222(11) 0.0013(11) 0.0087(9) 0.0010(11) C13 0.0236(11) 0.0207(12) 0.0206(10) 0.0027(11) 0.0026(8) 0.0006(11) C14 0.0244(11) 0.0201(13) 0.0235(11) 0.0016(11) 0.0091(9) 0.0021(11) C15 0.0199(11) 0.0164(12) 0.0242(11) 0.0020(11) 0.0060(8) 0.0023(10) C16 0.0219(11) 0.0158(12) 0.0272(11) 0.0018(11) 0.0074(9) 0.0019(10) C17 0.0204(11) 0.0219(13) 0.0294(12) 0.0022(12) 0.0030(9) 0.0026(11) C18 0.0265(12) 0.0205(14) 0.0238(11) 0.0016(11) 0.0017(9) 0.0033(11) C19 0.0312(13) 0.0311(17) 0.0256(12) 0.0018(13) 0.0001(10) 0.0013(13) C20 0.0258(12) 0.0251(14) 0.0228(11) 0.0016(11) 0.0061(9) 0.0034(11) C21 0.0226(11) 0.0191(12) 0.0223(11) 0.0023(11) 0.0065(9) 0.0027(11) C22 0.0230(11) 0.0217(13) 0.0254(11) 0.0011(11) 0.0095(9) 0.0046(11) C23 0.0193(10) 0.0226(13) 0.0275(11) 0.0026(12) 0.0060(9) 0.0023(11) C24 0.0191(11) 0.0268(14) 0.0228(11) 0.0014(11) 0.0076(9) -0.0004(10) C25 0.0205(11) 0.0321(16) 0.0226(11) 0.0064(11) 0.0014(9) 0.0000(11) C26 0.0268(12) 0.0352(16) 0.0348(13) 0.0058(13) 0.0084(10) 0.0048(13) C27 0.0370(16) 0.0430(19) 0.0265(14) 0.0010(13) 0.0019(12) 0.0072(14) C28 0.0281(14) 0.0435(19) 0.0379(15) 0.0166(14) 0.0018(12) -0.0022(13) C1S 0.044(4) 0.050(5) 0.038(4) -0.005(3) 0.011(3) -0.021(4) Cl1S 0.0439(17) 0.124(5) 0.085(3) -0.063(3) 0.028(2) -0.034(3) Cl2S 0.0611(19) 0.082(2) 0.0396(12) 0.0026(15) 0.0016(10) -0.0212(17) C1S' 0.044(4) 0.050(5) 0.038(4) -0.005(3) 0.011(3) -0.021(4) Cl1' 0.0439(17) 0.124(5) 0.085(3) -0.063(3) 0.028(2) -0.034(3) Cl2' 0.0611(19) 0.082(2) 0.0396(12) 0.0026(15) 0.0016(10) -0.0212(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.372(3) . ? N1 C8 1.376(3) . ? N1 C9 1.456(3) . ? N2 C24 1.345(3) . ? N2 C11 1.442(3) . ? N2 H2 0.8800 . ? O1 C12 1.189(4) . ? O2 C12 1.366(3) . ? O2 C13 1.397(3) . ? O3 C16 1.225(3) . ? O4 C20 1.217(3) . ? O5 C24 1.226(3) . ? O6 C24 1.345(3) . ? O6 C25 1.478(3) . ? C1 C2 1.399(3) . ? C1 C6 1.417(3) . ? C2 C3 1.382(4) . ? C2 H2A 0.9500 . ? C3 C4 1.409(4) . ? C3 H3 0.9500 . ? C4 C5 1.381(4) . ? C4 H4 0.9500 . ? C5 C6 1.399(3) . ? C5 H5 0.9500 . ? C6 C7 1.435(3) . ? C7 C8 1.369(4) . ? C7 C10 1.502(3) . ? C8 H8 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.548(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.510(3) . ? C11 H11 1.0000 . ? C13 C14 1.388(3) . ? C13 C23 1.390(3) . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C21 1.402(3) . ? C15 C16 1.496(3) . ? C16 C17 1.463(3) . ? C17 C18 1.342(4) . ? C17 H17 0.9500 . ? C18 C20 1.493(3) . ? C18 C19 1.499(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C21 1.489(3) . ? C21 C22 1.397(3) . ? C22 C23 1.381(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C25 C28 1.513(4) . ? C25 C26 1.516(4) . ? C25 C27 1.524(4) . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C1S Cl1S 1.760(6) . ? C1S Cl2S 1.760(6) . ? C1S H1S1 0.9900 . ? C1S H1S2 0.9900 . ? C1S' Cl2' 1.760(6) . ? C1S' Cl1' 1.760(6) . ? C1S' H1S3 0.9900 . ? C1S' H1S4 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 108.5(2) . . ? C1 N1 C9 124.5(2) . . ? C8 N1 C9 126.6(2) . . ? C24 N2 C11 119.6(2) . . ? C24 N2 H2 120.2 . . ? C11 N2 H2 120.2 . . ? C12 O2 C13 119.1(2) . . ? C24 O6 C25 120.0(2) . . ? N1 C1 C2 129.8(2) . . ? N1 C1 C6 107.8(2) . . ? C2 C1 C6 122.3(2) . . ? C3 C2 C1 117.5(2) . . ? C3 C2 H2A 121.3 . . ? C1 C2 H2A 121.3 . . ? C2 C3 C4 121.0(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 121.3(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 119.1(2) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C5 C6 C1 118.8(2) . . ? C5 C6 C7 134.4(2) . . ? C1 C6 C7 106.9(2) . . ? C8 C7 C6 106.3(2) . . ? C8 C7 C10 128.3(2) . . ? C6 C7 C10 125.2(2) . . ? C7 C8 N1 110.4(2) . . ? C7 C8 H8 124.8 . . ? N1 C8 H8 124.8 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 C11 114.5(2) . . ? C7 C10 H10A 108.6 . . ? C11 C10 H10A 108.6 . . ? C7 C10 H10B 108.6 . . ? C11 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? N2 C11 C12 109.9(2) . . ? N2 C11 C10 113.6(2) . . ? C12 C11 C10 110.1(2) . . ? N2 C11 H11 107.7 . . ? C12 C11 H11 107.7 . . ? C10 C11 H11 107.7 . . ? O1 C12 O2 123.8(2) . . ? O1 C12 C11 127.5(2) . . ? O2 C12 C11 108.7(2) . . ? C14 C13 C23 121.6(2) . . ? C14 C13 O2 121.1(2) . . ? C23 C13 O2 117.1(2) . . ? C15 C14 C13 118.5(2) . . ? C15 C14 H14 120.8 . . ? C13 C14 H14 120.8 . . ? C14 C15 C21 120.9(2) . . ? C14 C15 C16 119.5(2) . . ? C21 C15 C16 119.5(2) . . ? O3 C16 C17 122.4(2) . . ? O3 C16 C15 119.8(2) . . ? C17 C16 C15 117.8(2) . . ? C18 C17 C16 123.6(2) . . ? C18 C17 H17 118.2 . . ? C16 C17 H17 118.2 . . ? C17 C18 C20 120.1(2) . . ? C17 C18 C19 123.7(2) . . ? C20 C18 C19 116.2(2) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 C21 121.0(2) . . ? O4 C20 C18 120.9(2) . . ? C21 C20 C18 118.0(2) . . ? C22 C21 C15 119.2(2) . . ? C22 C21 C20 120.0(2) . . ? C15 C21 C20 120.8(2) . . ? C23 C22 C21 120.3(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C13 119.5(2) . . ? C22 C23 H23 120.2 . . ? C13 C23 H23 120.2 . . ? O5 C24 N2 123.7(3) . . ? O5 C24 O6 125.4(2) . . ? N2 C24 O6 110.9(2) . . ? O6 C25 C28 102.8(2) . . ? O6 C25 C26 110.0(2) . . ? C28 C25 C26 109.8(3) . . ? O6 C25 C27 110.1(2) . . ? C28 C25 C27 110.9(2) . . ? C26 C25 C27 112.8(2) . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? Cl1S C1S Cl2S 110.0(5) . . ? Cl1S C1S H1S1 109.7 . . ? Cl2S C1S H1S1 109.7 . . ? Cl1S C1S H1S2 109.7 . . ? Cl2S C1S H1S2 109.7 . . ? H1S1 C1S H1S2 108.2 . . ? Cl2' C1S' Cl1' 109.9(5) . . ? Cl2' C1S' H1S3 109.7 . . ? Cl1' C1S' H1S3 109.7 . . ? Cl2' C1S' H1S4 109.7 . . ? Cl1' C1S' H1S4 109.7 . . ? H1S3 C1S' H1S4 108.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 174.2(3) . . . . ? C9 N1 C1 C2 0.0(5) . . . . ? C8 N1 C1 C6 -2.7(3) . . . . ? C9 N1 C1 C6 -176.9(3) . . . . ? N1 C1 C2 C3 -178.8(3) . . . . ? C6 C1 C2 C3 -2.2(4) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 0.5(5) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C4 C5 C6 C1 -2.9(4) . . . . ? C4 C5 C6 C7 174.5(3) . . . . ? N1 C1 C6 C5 -179.1(3) . . . . ? C2 C1 C6 C5 3.7(4) . . . . ? N1 C1 C6 C7 2.8(3) . . . . ? C2 C1 C6 C7 -174.5(3) . . . . ? C5 C6 C7 C8 -179.5(3) . . . . ? C1 C6 C7 C8 -1.8(3) . . . . ? C5 C6 C7 C10 -4.0(5) . . . . ? C1 C6 C7 C10 173.7(3) . . . . ? C6 C7 C8 N1 0.2(3) . . . . ? C10 C7 C8 N1 -175.1(3) . . . . ? C1 N1 C8 C7 1.6(3) . . . . ? C9 N1 C8 C7 175.7(3) . . . . ? C8 C7 C10 C11 -87.3(3) . . . . ? C6 C7 C10 C11 98.3(3) . . . . ? C24 N2 C11 C12 149.9(2) . . . . ? C24 N2 C11 C10 -86.2(3) . . . . ? C7 C10 C11 N2 -49.5(3) . . . . ? C7 C10 C11 C12 74.3(3) . . . . ? C13 O2 C12 O1 1.1(4) . . . . ? C13 O2 C12 C11 -177.2(2) . . . . ? N2 C11 C12 O1 17.6(4) . . . . ? C10 C11 C12 O1 -108.3(3) . . . . ? N2 C11 C12 O2 -164.1(2) . . . . ? C10 C11 C12 O2 69.9(2) . . . . ? C12 O2 C13 C14 65.8(4) . . . . ? C12 O2 C13 C23 -119.4(3) . . . . ? C23 C13 C14 C15 0.9(4) . . . . ? O2 C13 C14 C15 175.5(2) . . . . ? C13 C14 C15 C21 0.0(4) . . . . ? C13 C14 C15 C16 -178.4(3) . . . . ? C14 C15 C16 O3 2.2(4) . . . . ? C21 C15 C16 O3 -176.2(3) . . . . ? C14 C15 C16 C17 -178.1(2) . . . . ? C21 C15 C16 C17 3.5(4) . . . . ? O3 C16 C17 C18 177.9(3) . . . . ? C15 C16 C17 C18 -1.8(4) . . . . ? C16 C17 C18 C20 -1.0(4) . . . . ? C16 C17 C18 C19 179.9(3) . . . . ? C17 C18 C20 O4 -177.8(3) . . . . ? C19 C18 C20 O4 1.4(4) . . . . ? C17 C18 C20 C21 2.1(4) . . . . ? C19 C18 C20 C21 -178.8(2) . . . . ? C14 C15 C21 C22 -0.9(4) . . . . ? C16 C15 C21 C22 177.5(3) . . . . ? C14 C15 C21 C20 179.2(3) . . . . ? C16 C15 C21 C20 -2.5(4) . . . . ? O4 C20 C21 C22 -0.4(5) . . . . ? C18 C20 C21 C22 179.8(3) . . . . ? O4 C20 C21 C15 179.6(3) . . . . ? C18 C20 C21 C15 -0.3(4) . . . . ? C15 C21 C22 C23 0.9(4) . . . . ? C20 C21 C22 C23 -179.2(3) . . . . ? C21 C22 C23 C13 0.0(4) . . . . ? C14 C13 C23 C22 -0.9(5) . . . . ? O2 C13 C23 C22 -175.7(2) . . . . ? C11 N2 C24 O5 -3.2(4) . . . . ? C11 N2 C24 O6 177.6(2) . . . . ? C25 O6 C24 O5 -0.2(4) . . . . ? C25 O6 C24 N2 179.0(2) . . . . ? C24 O6 C25 C28 177.7(2) . . . . ? C24 O6 C25 C26 -65.4(3) . . . . ? C24 O6 C25 C27 59.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N2 H2 O3 0.88 2.09 2.910(3) 154.3 4_546 yes C9 H9A O1 0.98 2.50 3.254(3) 133.2 4_556 yes C23 H23 O5 0.95 2.52 3.109(3) 120.1 2_656 yes C26 H26C O5 0.98 2.45 3.032(4) 117.9 . yes C27 H27A O5 0.98 2.38 2.934(4) 115.3 . yes _refine_diff_density_max 0.488 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.040 _shelx_res_file ; TITL c17058 : space group C2 c17058.res created by SHELXL-2017/1 at 19:31:20 on 01-Aug-2017 CELL 1.54178 23.7911 6.7169 17.0032 90.000 103.374 90.000 ZERR 2 0.0023 0.0006 0.0016 0.000 0.004 0.000 LATT -7 SYMM -X, Y, -Z SFAC C H N O Cl UNIT 114 116 8 24 4 TEMP -183 SIZE 0.30 0.03 0.02 REM FORM needle REM COLR red REM The dichloromethane solvent is modelled as disordered over two positions, REM each of which is repeated about the crystallographic 2-fold to give four REM positions in total. The largest difference map peak (~0.5 eA-3) looks REM it might be caused by yet more disorder, or it might be due to a partial REM occupancy water in approximately the same site as the DCM. Either way, REM There is no point in trying to model it. The minor component DCM needed REM very strong restraints to prevent geometry oscillation. ACTA L.S. 10 BOND $H LIST 4 CONF HTAB REM Instructions for potential hydrogen bonds EQIV $1 -x+1/2, y-1/2, -z+1 HTAB N2 O3_$1 EQIV $2 -x+1/2, y+1/2, -z+1 HTAB C9 O1_$2 EQIV $3 -x+1, y, -z+1 HTAB C23 O5_$3 HTAB C26 O5 HTAB C27 O5 FMAP 2 PLAN 5 REM EXTI 0.000320 : SU(EXTI) = 0.0002, not significant. WGHT 0.041700 1.471000 FVAR 0.42754 0.79752 N1 3 0.240184 0.769405 0.680773 11.00000 0.02149 0.02345 = 0.02442 0.00123 0.00614 0.00046 N2 3 0.425559 0.528256 0.669693 11.00000 0.01889 0.02574 = 0.02205 0.00319 0.00395 -0.00270 AFIX 43 H2 2 0.399931 0.431529 0.662616 11.00000 -1.20000 AFIX 0 O1 4 0.353871 0.493041 0.516253 11.00000 0.05394 0.03407 = 0.02373 0.00246 0.00272 -0.01406 O2 4 0.387160 0.785594 0.480267 11.00000 0.02793 0.02680 = 0.02116 0.00365 0.00242 -0.00300 O3 4 0.176810 0.795989 0.325394 11.00000 0.02305 0.02738 = 0.03130 0.00370 0.01023 0.00466 O4 4 0.298295 0.743090 0.098292 11.00000 0.03276 0.05067 = 0.02291 -0.00042 0.00887 0.00276 O5 4 0.511989 0.642733 0.741131 11.00000 0.02078 0.03246 = 0.02978 0.00511 0.00379 -0.00620 O6 4 0.473111 0.352278 0.774348 11.00000 0.02027 0.03241 = 0.02501 0.00737 0.00153 -0.00350 C1 1 0.271417 0.759035 0.759355 11.00000 0.02470 0.01869 = 0.02442 -0.00060 0.00783 0.00031 C2 1 0.252429 0.737887 0.830860 11.00000 0.02938 0.01944 = 0.02853 -0.00114 0.01326 -0.00017 AFIX 43 H2A 2 0.212521 0.725660 0.830069 11.00000 -1.20000 AFIX 0 C3 1 0.293932 0.735460 0.902679 11.00000 0.03789 0.02286 = 0.02420 -0.00023 0.01259 0.00190 AFIX 43 H3 2 0.282436 0.720982 0.952288 11.00000 -1.20000 AFIX 0 C4 1 0.353038 0.754126 0.903474 11.00000 0.03389 0.02585 = 0.02357 -0.00066 0.00369 0.00113 AFIX 43 H4 2 0.380729 0.751002 0.953659 11.00000 -1.20000 AFIX 0 C5 1 0.371537 0.776873 0.832778 11.00000 0.02748 0.02267 = 0.02592 -0.00151 0.00628 -0.00136 AFIX 43 H5 2 0.411570 0.787256 0.834113 11.00000 -1.20000 AFIX 0 C6 1 0.330508 0.784415 0.759168 11.00000 0.02424 0.01837 = 0.02558 -0.00100 0.00773 -0.00225 C7 1 0.333171 0.820445 0.676922 11.00000 0.02518 0.01818 = 0.02405 0.00020 0.00823 0.00061 C8 1 0.277519 0.809492 0.631916 11.00000 0.02873 0.02084 = 0.02175 -0.00032 0.00756 0.00140 AFIX 43 H8 2 0.266278 0.827091 0.574994 11.00000 -1.20000 AFIX 0 C9 1 0.177415 0.759705 0.656057 11.00000 0.02264 0.02491 = 0.03172 0.00154 0.00561 0.00191 AFIX 137 H9A 2 0.165526 0.746310 0.597145 11.00000 -1.50000 H9B 2 0.160844 0.881750 0.672800 11.00000 -1.50000 H9C 2 0.163632 0.644528 0.681592 11.00000 -1.50000 AFIX 0 C10 1 0.386723 0.875545 0.649403 11.00000 0.02723 0.02496 = 0.02232 0.00042 0.00772 -0.00404 AFIX 23 H10A 2 0.414677 0.936564 0.695342 11.00000 -1.20000 H10B 2 0.376510 0.977402 0.606377 11.00000 -1.20000 AFIX 0 C11 1 0.416515 0.698935 0.616852 11.00000 0.01805 0.02632 = 0.02126 0.00349 0.00586 -0.00188 AFIX 13 H11 2 0.455256 0.745700 0.611046 11.00000 -1.20000 AFIX 0 C12 1 0.382192 0.639120 0.533982 11.00000 0.02257 0.02431 = 0.02224 0.00128 0.00868 0.00100 C13 1 0.356764 0.767227 0.399807 11.00000 0.02365 0.02068 = 0.02056 0.00269 0.00263 0.00061 C14 1 0.296824 0.771866 0.378970 11.00000 0.02441 0.02013 = 0.02354 0.00165 0.00906 0.00207 AFIX 43 H14 2 0.275250 0.778157 0.419454 11.00000 -1.20000 AFIX 0 C15 1 0.269133 0.767105 0.297659 11.00000 0.01985 0.01644 = 0.02423 0.00205 0.00601 0.00233 C16 1 0.204601 0.777447 0.273500 11.00000 0.02187 0.01584 = 0.02724 0.00182 0.00738 0.00187 C17 1 0.177028 0.765639 0.187268 11.00000 0.02044 0.02192 = 0.02941 0.00220 0.00297 0.00265 AFIX 43 H17 2 0.136027 0.768275 0.171659 11.00000 -1.20000 AFIX 0 C18 1 0.206451 0.751290 0.129000 11.00000 0.02654 0.02046 = 0.02380 0.00156 0.00174 0.00328 C19 1 0.178230 0.739003 0.040661 11.00000 0.03119 0.03111 = 0.02556 0.00176 0.00011 0.00125 AFIX 137 H19A 2 0.188430 0.856919 0.012988 11.00000 -1.50000 H19B 2 0.136198 0.732962 0.033570 11.00000 -1.50000 H19C 2 0.191614 0.619097 0.017674 11.00000 -1.50000 AFIX 0 C20 1 0.270962 0.749970 0.150533 11.00000 0.02585 0.02509 = 0.02284 0.00157 0.00610 0.00343 C21 1 0.300805 0.757816 0.237723 11.00000 0.02262 0.01906 = 0.02229 0.00233 0.00655 0.00273 C22 1 0.361127 0.756127 0.260608 11.00000 0.02305 0.02169 = 0.02545 0.00110 0.00947 0.00458 AFIX 43 H22 2 0.382998 0.751773 0.220440 11.00000 -1.20000 AFIX 0 C23 1 0.389071 0.760765 0.341398 11.00000 0.01930 0.02265 = 0.02748 0.00258 0.00596 0.00231 AFIX 43 H23 2 0.430080 0.759547 0.356939 11.00000 -1.20000 AFIX 0 C24 1 0.473399 0.517776 0.729862 11.00000 0.01910 0.02685 = 0.02279 0.00140 0.00761 -0.00035 C25 1 0.522226 0.309201 0.843104 11.00000 0.02048 0.03213 = 0.02262 0.00640 0.00140 0.00000 C26 1 0.576317 0.271131 0.812690 11.00000 0.02685 0.03523 = 0.03483 0.00580 0.00836 0.00476 AFIX 137 H26A 2 0.568935 0.164253 0.772375 11.00000 -1.50000 H26B 2 0.607868 0.231731 0.858045 11.00000 -1.50000 H26C 2 0.587127 0.392791 0.787983 11.00000 -1.50000 AFIX 0 C27 1 0.529633 0.477538 0.904773 11.00000 0.03702 0.04303 = 0.02652 0.00102 0.00191 0.00717 AFIX 137 H27A 2 0.544970 0.595461 0.882979 11.00000 -1.50000 H27B 2 0.556566 0.435831 0.954796 11.00000 -1.50000 H27C 2 0.492124 0.509547 0.916191 11.00000 -1.50000 AFIX 0 C28 1 0.503497 0.119331 0.877509 11.00000 0.02813 0.04353 = 0.03791 0.01656 0.00183 -0.00217 AFIX 137 H28A 2 0.496984 0.015387 0.835939 11.00000 -1.50000 H28B 2 0.467636 0.143429 0.895025 11.00000 -1.50000 H28C 2 0.533738 0.076158 0.923853 11.00000 -1.50000 AFIX 0 REM Disordered solvent, DCM SADI 0.001 C1S Cl1S C1S Cl2S C1S' Cl1' C1S' Cl2' SAME 0.001 C1S' Cl1' Cl2' RIGU C1S Cl1S Cl2S RIGU C1S' Cl1' Cl2' SIMU 0.05 C1S > Cl2' EADP C1S C1S' EADP Cl1S Cl1' EADP Cl2S Cl2' PART -1 C1S 1 0.480337 0.176910 0.512928 20.50000 0.04361 0.05006 = 0.03810 -0.00524 0.01062 -0.02130 AFIX 23 H1S1 2 0.441092 0.199348 0.521617 20.50000 -1.20000 H1S2 2 0.492948 0.041716 0.532600 20.50000 -1.20000 AFIX 0 CL1S 5 0.528244 0.354870 0.567371 20.50000 0.04388 0.12414 = 0.08482 -0.06314 0.02792 -0.03361 CL2S 5 0.478729 0.194972 0.409168 20.50000 0.06109 0.08156 = 0.03956 0.00261 0.00157 -0.02122 PART -2 C1S' 1 0.504149 0.459141 0.508844 -20.50000 0.04361 0.05006 = 0.03810 -0.00524 0.01062 -0.02130 AFIX 23 H1S3 2 0.478374 0.554338 0.527792 -20.50000 -1.20000 H1S4 2 0.537178 0.534493 0.497568 -20.50000 -1.20000 AFIX 0 CL1' 5 0.529507 0.280324 0.584391 -20.50000 0.04388 0.12414 = 0.08482 -0.06314 0.02792 -0.03361 CL2' 5 0.466170 0.341114 0.419953 -20.50000 0.06109 0.08156 = 0.03956 0.00261 0.00157 -0.02122 PART 0 HKLF 4 REM c17058 : space group C2 REM R1 = 0.0380 for 4832 Fo > 4sig(Fo) and 0.0427 for all 5266 data REM 367 parameters refined using 86 restraints END WGHT 0.0418 1.4682 REM Instructions for potential hydrogen bonds HTAB N2 O3_$1 HTAB C9 O1_$2 HTAB C23 O5_$3 HTAB C26 O5 HTAB C27 O5 HTAB C1S'^b O2 HTAB C1S'^b O2_$3 REM Highest difference peak 0.488, deepest hole -0.298, 1-sigma level 0.040 Q1 1 0.5117 0.0439 0.5098 11.00000 0.05 0.49 Q2 1 0.2855 0.7599 0.1936 11.00000 0.05 0.20 Q3 1 0.4877 0.2241 0.5352 11.00000 0.05 0.19 Q4 1 0.3328 0.8045 0.7194 11.00000 0.05 0.17 Q5 1 0.1912 0.7473 0.0870 11.00000 0.05 0.17 ; _shelx_res_checksum 55334