##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
# #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1869537'
_audit_creation_method SHELXL-2013
_chemical_name_systematic
;\
(1aR,4E,7aS,8E,10aS,10bR)-\
8-(2-Aminobenzylidene)-1a,5-dimethyl-2,3,6,7,7a,8,10a,10b-\
octahydrooxireno[2',3':9,10]cyclodeca[1,2-b]furan-9(1aH)-one
;
_chemical_name_common
;
13-(E)-(2-Aminobenzylidene)parthenolide
;
_chemical_formula_moiety 'C21 H25 N O3'
_chemical_formula_sum 'C21 H25 N O3'
_chemical_formula_iupac 'C21 H25 N O3'
_chemical_formula_weight 339.42
_chemical_melting_point ?
_chemical_absolute_configuration ?
_space_group_crystal_system monoclinic
_space_group_name_H-M_alt 'P 21'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 11.6136(3)
_cell_length_b 6.24030(10)
_cell_length_c 12.6875(3)
_cell_angle_alpha 90
_cell_angle_beta 104.3850(10)
_cell_angle_gamma 90
_cell_volume 890.67(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9958
_cell_measurement_theta_min 3.93
_cell_measurement_theta_max 68.15
_cell_measurement_temperature 90.0(2)
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.160
_exptl_crystal_size_mid 0.120
_exptl_crystal_size_min 0.080
_exptl_crystal_density_diffrn 1.266
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_F_000 364
_exptl_absorpt_coefficient_mu 0.671
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_min 0.840
_exptl_absorpt_correction_T_max 0.942
_exptl_special_details
;
The crystal was mounted with polyisobutene oil on the tip of a fine glass
fibre, fastened in a copper mounting pin with electrical solder. It was
placed directly into the cold stream of a liquid nitrogen based cryostat,
according to published methods (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_source 'fine-focus rotating anode'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_measurement_device_type 'Bruker X8 Proteum'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean 5.6
_diffrn_reflns_number 24004
_diffrn_reflns_av_R_equivalents 0.0411
_diffrn_reflns_av_unetI/netI 0.0205
_diffrn_reflns_theta_min 3.596
_diffrn_reflns_theta_max 68.147
_diffrn_reflns_theta_full 67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_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.
;
_reflns_number_total 2592
_reflns_number_gt 2559
_reflns_threshold_expression 'I > 2\s(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0322
_refine_ls_R_factor_gt 0.0318
_refine_ls_wR_factor_gt 0.0837
_refine_ls_wR_factor_ref 0.0842
_refine_ls_goodness_of_fit_ref 1.076
_refine_ls_restrained_S_all 1.076
_refine_ls_number_reflns 2592
_refine_ls_number_parameters 238
_refine_ls_number_restraints 2
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.1894P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.177
_refine_diff_density_min -0.139
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_abs_structure_details
;
Flack x determined using 811 quotients
[(I^+^)-(I^-^)]/[(I^+^)+(I^-^)]
(Parsons et al., 2013), as calculated by PLATON (Spek,
2009).
;
_refine_ls_abs_structure_Flack 0.07(7)
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'
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2013 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)
;
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.15259(14) 0.2877(3) -0.01598(12) 0.0449(5) Uani d 1 . .
O O2 0.37973(12) 0.4845(3) 0.01116(10) 0.0310(3) Uani d 1 . .
O O3 0.57392(13) 0.4878(3) 0.08619(10) 0.0338(3) Uani d 1 . .
C C1 0.0887(2) 0.3088(4) -0.34185(17) 0.0352(5) Uani d 1 . .
H H1 0.1376 0.1884 -0.3456 0.042 Uiso calc 1 . .
C C2 -0.0258(2) 0.2614(4) -0.31056(19) 0.0398(6) Uani d 1 . .
H H2A -0.0672 0.1415 -0.3555 0.048 Uiso calc 1 . .
H H2B -0.0781 0.3887 -0.3256 0.048 Uiso calc 1 . .
C C3 -0.0032(2) 0.2016(5) -0.18904(19) 0.0408(6) Uani d 1 . .
H H3A -0.0797 0.1974 -0.1680 0.049 Uiso calc 1 . .
H H3B 0.0331 0.0573 -0.1769 0.049 Uiso calc 1 . .
C C4 0.07850(19) 0.3630(4) -0.11934(17) 0.0353(5) Uani d 1 . .
C C5 0.20641(18) 0.3246(4) -0.10509(17) 0.0328(5) Uani d 1 . .
H H5 0.2251 0.1905 -0.1407 0.039 Uiso calc 1 . .
C C6 0.29816(17) 0.4982(4) -0.09641(14) 0.0288(4) Uani d 1 . .
H H6 0.2587 0.6418 -0.1064 0.035 Uiso calc 1 . .
C C7 0.37413(16) 0.4677(4) -0.18048(14) 0.0262(4) Uani d 1 . .
H H7 0.3626 0.3171 -0.2080 0.031 Uiso calc 1 . .
C C8 0.34284(18) 0.6194(4) -0.28030(15) 0.0287(5) Uani d 1 . .
H H8A 0.3081 0.7530 -0.2596 0.034 Uiso calc 1 . .
H H8B 0.4167 0.6578 -0.3014 0.034 Uiso calc 1 . .
C C9 0.25450(18) 0.5184(4) -0.37888(14) 0.0314(5) Uani d 1 . .
H H9A 0.2521 0.6076 -0.4439 0.038 Uiso calc 1 . .
H H9B 0.2840 0.3748 -0.3924 0.038 Uiso calc 1 . .
C C10 0.12982(17) 0.4963(4) -0.36473(13) 0.0286(4) Uani d 1 . .
C C11 0.49909(17) 0.4865(4) -0.11042(13) 0.0255(4) Uani d 1 . .
C C12 0.49328(19) 0.4875(4) 0.00462(15) 0.0280(4) Uani d 1 . .
C C13 0.60415(17) 0.5038(4) -0.13427(14) 0.0282(4) Uani d 1 . .
H H13 0.6711 0.5207 -0.0742 0.034 Uiso calc 1 . .
C C14 0.0631(2) 0.7032(4) -0.37465(19) 0.0395(6) Uani d 1 . .
H H14A -0.0194 0.6752 -0.3727 0.059 Uiso calc 1 . .
H H14B 0.0644 0.7725 -0.4436 0.059 Uiso calc 1 . .
H H14C 0.1005 0.7976 -0.3141 0.059 Uiso calc 1 . .
C C15 0.0281(2) 0.5807(5) -0.1117(2) 0.0436(6) Uani d 1 . .
H H15A -0.0376 0.5705 -0.0762 0.065 Uiso calc 1 . .
H H15B -0.0013 0.6402 -0.1850 0.065 Uiso calc 1 . .
H H15C 0.0901 0.6745 -0.0690 0.065 Uiso calc 1 . .
C C16 0.62889(16) 0.5001(4) -0.24275(14) 0.0279(4) Uani d 1 . .
C C17 0.58739(18) 0.3343(4) -0.31796(15) 0.0301(4) Uani d 0.901(4) A 1
N N1 0.52374(18) 0.1616(4) -0.29365(15) 0.0308(5) Uani d 0.901(4) A 1
H H1N 0.524(3) 0.047(5) -0.334(2) 0.046 Uiso d 0.901(4) A 1
H H2N 0.530(3) 0.136(6) -0.225(2) 0.046 Uiso d 0.901(4) A 1
C C17' 0.58739(18) 0.3343(4) -0.31796(15) 0.0301(4) Uani d 0.099(4) A 2
H H17' 0.5450 0.2160 -0.2992 0.036 Uiso calc 0.099(4) A 2
C C18 0.61026(19) 0.3482(5) -0.42116(16) 0.0349(5) Uani d 1 . .
H H18 0.5830 0.2377 -0.4728 0.042 Uiso calc 1 A 1
C C19 0.67180(19) 0.5197(5) -0.44896(16) 0.0382(6) Uani d 1 . .
H H19 0.6843 0.5279 -0.5201 0.046 Uiso calc 1 . .
C C20 0.71561(19) 0.6804(4) -0.37407(18) 0.0372(5) Uani d 1 . .
H H20 0.7588 0.7973 -0.3932 0.045 Uiso calc 1 A 1
C C21 0.69556(18) 0.6680(4) -0.27111(17) 0.0315(5) Uani d 0.901(4) A 1
H H21 0.7275 0.7751 -0.2188 0.038 Uiso calc 0.901(4) A 1
C C21' 0.69556(18) 0.6680(4) -0.27111(17) 0.0315(5) Uani d 0.099(4) A 2
N N1' 0.7329(16) 0.843(3) -0.2219(13) 0.0308(5) Uani d 0.099(4) A 2
H H1N' 0.7209 0.8389 -0.1538 0.046 Uiso d 0.099(4) A 2
H H2N' 0.8119 0.8571 -0.2175 0.046 Uiso d 0.099(4) 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_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0318(8) 0.0637(13) 0.0419(8) 0.0018(9) 0.0144(6) 0.0236(8)
O2 0.0381(7) 0.0293(8) 0.0295(6) 0.0003(8) 0.0160(5) 0.0015(7)
O3 0.0452(8) 0.0288(8) 0.0258(6) -0.0091(8) 0.0060(6) -0.0006(7)
C1 0.0382(12) 0.0304(13) 0.0368(10) 0.0021(11) 0.0093(9) -0.0045(9)
C2 0.0356(12) 0.0331(14) 0.0491(12) -0.0049(10) 0.0075(9) 0.0010(10)
C3 0.0324(11) 0.0388(15) 0.0542(13) 0.0006(11) 0.0162(9) 0.0129(11)
C4 0.0310(11) 0.0456(15) 0.0331(10) 0.0096(11) 0.0154(8) 0.0133(10)
C5 0.0325(10) 0.0298(12) 0.0401(10) 0.0067(10) 0.0166(8) 0.0112(10)
C6 0.0311(10) 0.0266(11) 0.0314(9) 0.0056(10) 0.0130(7) 0.0072(9)
C7 0.0269(9) 0.0251(11) 0.0279(8) 0.0011(9) 0.0096(7) 0.0014(8)
C8 0.0277(10) 0.0315(12) 0.0282(9) 0.0012(9) 0.0094(7) 0.0052(8)
C9 0.0381(11) 0.0335(13) 0.0246(8) 0.0022(10) 0.0114(7) -0.0011(9)
C10 0.0314(10) 0.0319(12) 0.0205(8) 0.0005(11) 0.0029(7) -0.0023(9)
C11 0.0320(10) 0.0204(10) 0.0251(8) 0.0004(9) 0.0090(7) -0.0003(8)
C12 0.0389(10) 0.0178(10) 0.0287(8) -0.0027(10) 0.0110(7) 0.0005(9)
C13 0.0277(9) 0.0281(11) 0.0276(8) 0.0002(10) 0.0048(7) -0.0002(9)
C14 0.0334(11) 0.0383(15) 0.0446(12) 0.0063(11) 0.0058(9) 0.0133(11)
C15 0.0393(12) 0.0528(17) 0.0417(12) 0.0142(12) 0.0161(9) -0.0052(11)
C16 0.0221(8) 0.0335(12) 0.0285(8) 0.0047(10) 0.0071(7) 0.0024(9)
C17 0.0266(9) 0.0338(12) 0.0314(9) 0.0032(10) 0.0103(7) -0.0003(9)
N1 0.0382(11) 0.0292(12) 0.0270(9) -0.0012(9) 0.0122(7) -0.0032(8)
C17' 0.0266(9) 0.0338(12) 0.0314(9) 0.0032(10) 0.0103(7) -0.0003(9)
C18 0.0333(10) 0.0435(15) 0.0299(9) 0.0041(11) 0.0119(8) -0.0012(10)
C19 0.0331(10) 0.0509(17) 0.0332(10) 0.0071(11) 0.0134(8) 0.0107(11)
C20 0.0274(10) 0.0412(15) 0.0456(12) 0.0013(11) 0.0140(8) 0.0125(11)
C21 0.0225(9) 0.0351(13) 0.0371(10) 0.0021(9) 0.0075(7) 0.0011(9)
C21' 0.0225(9) 0.0351(13) 0.0371(10) 0.0021(9) 0.0075(7) 0.0011(9)
N1' 0.0382(11) 0.0292(12) 0.0270(9) -0.0012(9) 0.0122(7) -0.0032(8)
_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 . 1.440(2) ?
O1 C4 . 1.456(2) ?
O2 C12 . 1.342(3) ?
O2 C6 . 1.458(2) ?
O3 C12 . 1.211(3) ?
C1 C10 . 1.323(4) ?
C1 C2 . 1.508(3) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.544(3) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.510(4) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.471(3) ?
C4 C15 . 1.492(4) ?
C5 C6 . 1.504(3) ?
C5 H5 . 1.0000 ?
C6 C7 . 1.556(2) ?
C6 H6 . 1.0000 ?
C7 C11 . 1.506(3) ?
C7 C8 . 1.550(3) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.541(3) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.509(3) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C14 . 1.496(3) ?
C11 C13 . 1.332(3) ?
C11 C12 . 1.478(2) ?
C13 C16 . 1.474(2) ?
C13 H13 . 0.9500 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 C21 . 1.402(3) ?
C16 C17 . 1.409(3) ?
C17 N1 . 1.384(3) ?
C17 C18 . 1.402(3) ?
N1 H1N . 0.88(3) ?
N1 H2N . 0.87(3) ?
C18 C19 . 1.381(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.388(4) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.385(3) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
N1' H1N' . 0.9100 ?
N1' H2N' . 0.9100 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 O1 C4 . . 61.05(13) ?
C12 O2 C6 . . 111.18(13) ?
C10 C1 C2 . . 128.4(2) ?
C10 C1 H1 . . 115.8 ?
C2 C1 H1 . . 115.8 ?
C1 C2 C3 . . 111.59(19) ?
C1 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
C1 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
C4 C3 C2 . . 110.5(2) ?
C4 C3 H3A . . 109.6 ?
C2 C3 H3A . . 109.6 ?
C4 C3 H3B . . 109.6 ?
C2 C3 H3B . . 109.6 ?
H3A C3 H3B . . 108.1 ?
O1 C4 C5 . . 58.93(13) ?
O1 C4 C15 . . 112.9(2) ?
C5 C4 C15 . . 122.7(2) ?
O1 C4 C3 . . 117.2(2) ?
C5 C4 C3 . . 115.6(2) ?
C15 C4 C3 . . 116.50(19) ?
O1 C5 C4 . . 60.02(12) ?
O1 C5 C6 . . 119.7(2) ?
C4 C5 C6 . . 124.6(2) ?
O1 C5 H5 . . 114.0 ?
C4 C5 H5 . . 114.0 ?
C6 C5 H5 . . 114.0 ?
O2 C6 C5 . . 108.06(16) ?
O2 C6 C7 . . 106.71(15) ?
C5 C6 C7 . . 111.96(18) ?
O2 C6 H6 . . 110.0 ?
C5 C6 H6 . . 110.0 ?
C7 C6 H6 . . 110.0 ?
C11 C7 C8 . . 115.51(17) ?
C11 C7 C6 . . 102.31(14) ?
C8 C7 C6 . . 115.32(17) ?
C11 C7 H7 . . 107.7 ?
C8 C7 H7 . . 107.7 ?
C6 C7 H7 . . 107.7 ?
C9 C8 C7 . . 112.77(18) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C10 C9 C8 . . 113.94(16) ?
C10 C9 H9A . . 108.8 ?
C8 C9 H9A . . 108.8 ?
C10 C9 H9B . . 108.8 ?
C8 C9 H9B . . 108.8 ?
H9A C9 H9B . . 107.7 ?
C1 C10 C14 . . 125.06(19) ?
C1 C10 C9 . . 121.1(2) ?
C14 C10 C9 . . 113.8(2) ?
C13 C11 C12 . . 119.54(17) ?
C13 C11 C7 . . 132.42(16) ?
C12 C11 C7 . . 108.03(16) ?
O3 C12 O2 . . 120.69(17) ?
O3 C12 C11 . . 128.95(19) ?
O2 C12 C11 . . 110.35(16) ?
C11 C13 C16 . . 127.78(17) ?
C11 C13 H13 . . 116.1 ?
C16 C13 H13 . . 116.1 ?
C10 C14 H14A . . 109.5 ?
C10 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C10 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C4 C15 H15A . . 109.5 ?
C4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C21 C16 C17 . . 119.53(17) ?
C21 C16 C13 . . 118.4(2) ?
C17 C16 C13 . . 122.1(2) ?
N1 C17 C18 . . 119.5(2) ?
N1 C17 C16 . . 122.18(18) ?
C18 C17 C16 . . 118.4(2) ?
C17 N1 H1N . . 115(2) ?
C17 N1 H2N . . 117(2) ?
H1N N1 H2N . . 115(3) ?
C19 C18 C17 . . 121.1(2) ?
C19 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
C18 C19 C20 . . 120.67(19) ?
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
C21 C20 C19 . . 119.1(2) ?
C21 C20 H20 . . 120.4 ?
C19 C20 H20 . . 120.4 ?
C20 C21 C16 . . 121.1(2) ?
C20 C21 H21 . . 119.4 ?
C16 C21 H21 . . 119.4 ?
H1N' N1' H2N' . . 109.5 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 C1 C2 C3 . . . . -107.8(3) ?
C1 C2 C3 C4 . . . . 49.0(3) ?
C5 O1 C4 C15 . . . . -115.5(2) ?
C5 O1 C4 C3 . . . . 104.9(2) ?
C2 C3 C4 O1 . . . . -151.63(19) ?
C2 C3 C4 C5 . . . . -85.0(2) ?
C2 C3 C4 C15 . . . . 70.2(2) ?
C4 O1 C5 C6 . . . . 115.1(3) ?
C15 C4 C5 O1 . . . . 98.8(2) ?
C3 C4 C5 O1 . . . . -107.7(2) ?
O1 C4 C5 C6 . . . . -107.3(2) ?
C15 C4 C5 C6 . . . . -8.5(3) ?
C3 C4 C5 C6 . . . . 145.1(2) ?
C12 O2 C6 C5 . . . . 131.12(19) ?
C12 O2 C6 C7 . . . . 10.6(3) ?
O1 C5 C6 O2 . . . . 44.4(3) ?
C4 C5 C6 O2 . . . . 116.6(2) ?
O1 C5 C6 C7 . . . . 161.60(18) ?
C4 C5 C6 C7 . . . . -126.2(2) ?
O2 C6 C7 C11 . . . . -11.8(2) ?
C5 C6 C7 C11 . . . . -129.85(19) ?
O2 C6 C7 C8 . . . . -138.03(19) ?
C5 C6 C7 C8 . . . . 103.9(2) ?
C11 C7 C8 C9 . . . . 146.42(18) ?
C6 C7 C8 C9 . . . . -94.4(2) ?
C7 C8 C9 C10 . . . . 71.1(2) ?
C2 C1 C10 C14 . . . . -6.3(4) ?
C2 C1 C10 C9 . . . . 171.1(2) ?
C8 C9 C10 C1 . . . . -103.1(2) ?
C8 C9 C10 C14 . . . . 74.6(2) ?
C8 C7 C11 C13 . . . . -43.4(4) ?
C6 C7 C11 C13 . . . . -169.5(3) ?
C8 C7 C11 C12 . . . . 135.47(19) ?
C6 C7 C11 C12 . . . . 9.4(2) ?
C6 O2 C12 O3 . . . . 176.5(2) ?
C6 O2 C12 C11 . . . . -4.5(3) ?
C13 C11 C12 O3 . . . . -5.6(4) ?
C7 C11 C12 O3 . . . . 175.3(2) ?
C13 C11 C12 O2 . . . . 175.4(2) ?
C7 C11 C12 O2 . . . . -3.6(3) ?
C12 C11 C13 C16 . . . . 178.2(2) ?
C7 C11 C13 C16 . . . . -3.0(4) ?
C11 C13 C16 C21 . . . . 127.5(3) ?
C11 C13 C16 C17 . . . . -52.3(3) ?
C21 C16 C17 N1 . . . . 178.3(2) ?
C13 C16 C17 N1 . . . . -1.9(3) ?
C21 C16 C17 C18 . . . . -2.7(3) ?
C13 C16 C17 C18 . . . . 177.11(19) ?
N1 C17 C18 C19 . . . . 179.0(2) ?
C16 C17 C18 C19 . . . . -0.1(3) ?
C17 C18 C19 C20 . . . . 1.8(3) ?
C18 C19 C20 C21 . . . . -0.8(3) ?
C19 C20 C21 C16 . . . . -2.0(3) ?
C17 C16 C21 C20 . . . . 3.8(3) ?
C13 C16 C21 C20 . . . . -176.0(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C5 H5 O3 2_645 1.00 2.59 3.268(3) 125
C7 H7 O3 2_645 1.00 2.57 3.226(3) 123
C15 H15A O1 2_555 0.98 2.40 3.223(3) 141
_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.
;
_shelx_estimated_absorpt_T_min 0.900
_shelx_estimated_absorpt_T_max 0.948
_shelxl_version_number .2013
_iucr_refine_instructions_details
;
TITL x13430 in P2(1)
CELL 1.54178 11.6136 6.2403 12.6875 90.000 104.385 90.000
ZERR 2.00 0.0003 0.0001 0.0003 0.000 0.001 0.000
LATT -1
SYMM -X, 1/2+Y, -Z
SFAC C H N O
UNIT 42 50 2 6
TEMP -183.000
SIZE 0.16 0.12 0.08
REM COLR colourless
SHEL 999 0.83
L.S. 10
BOND $H
CONF
HTAB
ACTA
LIST 4
FMAP 2
PLAN 10
REM EXTI 0.002061, SU = 0.00120: not significant.
WGHT 0.044900 0.189400
FVAR 1.37712 0.90094
O1 4 0.152593 0.287739 -0.015976 11.00000 0.03178 0.06371 =
0.04189 0.02356 0.01438 0.00179
O2 4 0.379726 0.484456 0.011162 11.00000 0.03812 0.02927 =
0.02953 0.00148 0.01601 0.00025
O3 4 0.573923 0.487799 0.086195 11.00000 0.04521 0.02883 =
0.02578 -0.00064 0.00601 -0.00909
C1 1 0.088721 0.308792 -0.341848 11.00000 0.03817 0.03041 =
0.03685 -0.00447 0.00926 0.00209
AFIX 43
H1 2 0.137635 0.188441 -0.345610 11.00000 -1.20000
AFIX 0
C2 1 -0.025761 0.261352 -0.310556 11.00000 0.03562 0.03308 =
0.04907 0.00103 0.00748 -0.00490
AFIX 23
H2A 2 -0.067191 0.141488 -0.355524 11.00000 -1.20000
H2B 2 -0.078090 0.388743 -0.325615 11.00000 -1.20000
AFIX 0
C3 1 -0.003173 0.201571 -0.189041 11.00000 0.03241 0.03880 =
0.05418 0.01292 0.01618 0.00059
AFIX 23
H3A 2 -0.079701 0.197427 -0.167971 11.00000 -1.20000
H3B 2 0.033133 0.057265 -0.176946 11.00000 -1.20000
AFIX 0
C4 1 0.078496 0.363001 -0.119337 11.00000 0.03100 0.04562 =
0.03311 0.01326 0.01535 0.00958
C5 1 0.206409 0.324601 -0.105094 11.00000 0.03252 0.02983 =
0.04008 0.01115 0.01660 0.00667
AFIX 13
H5 2 0.225068 0.190529 -0.140726 11.00000 -1.20000
AFIX 0
C6 1 0.298163 0.498168 -0.096409 11.00000 0.03114 0.02663 =
0.03145 0.00721 0.01303 0.00565
AFIX 13
H6 2 0.258727 0.641768 -0.106432 11.00000 -1.20000
AFIX 0
C7 1 0.374132 0.467694 -0.180479 11.00000 0.02695 0.02508 =
0.02792 0.00141 0.00962 0.00112
AFIX 13
H7 2 0.362610 0.317075 -0.207996 11.00000 -1.20000
AFIX 0
C8 1 0.342836 0.619383 -0.280303 11.00000 0.02767 0.03151 =
0.02819 0.00516 0.00945 0.00116
AFIX 23
H8A 2 0.308056 0.753025 -0.259629 11.00000 -1.20000
H8B 2 0.416723 0.657824 -0.301439 11.00000 -1.20000
AFIX 0
C9 1 0.254504 0.518426 -0.378879 11.00000 0.03806 0.03352 =
0.02462 -0.00106 0.01135 0.00225
AFIX 23
H9A 2 0.252115 0.607615 -0.443918 11.00000 -1.20000
H9B 2 0.284030 0.374777 -0.392447 11.00000 -1.20000
AFIX 0
C10 1 0.129824 0.496255 -0.364726 11.00000 0.03140 0.03191 =
0.02047 -0.00228 0.00290 0.00052
C11 1 0.499091 0.486450 -0.110420 11.00000 0.03196 0.02040 =
0.02508 -0.00032 0.00901 0.00044
C12 1 0.493281 0.487532 0.004621 11.00000 0.03893 0.01784 =
0.02873 0.00048 0.01099 -0.00270
C13 1 0.604146 0.503844 -0.134275 11.00000 0.02774 0.02815 =
0.02761 -0.00017 0.00483 0.00018
AFIX 43
H13 2 0.671121 0.520675 -0.074194 11.00000 -1.20000
AFIX 0
C14 1 0.063055 0.703242 -0.374647 11.00000 0.03338 0.03829 =
0.04465 0.01333 0.00579 0.00627
AFIX 137
H14A 2 -0.019430 0.675216 -0.372733 11.00000 -1.50000
H14B 2 0.064386 0.772538 -0.443649 11.00000 -1.50000
H14C 2 0.100461 0.797596 -0.314058 11.00000 -1.50000
AFIX 0
C15 1 0.028120 0.580723 -0.111726 11.00000 0.03933 0.05283 =
0.04170 -0.00516 0.01612 0.01421
AFIX 137
H15A 2 -0.037553 0.570539 -0.076158 11.00000 -1.50000
H15B 2 -0.001306 0.640172 -0.184980 11.00000 -1.50000
H15C 2 0.090126 0.674479 -0.069040 11.00000 -1.50000
AFIX 0
C16 1 0.628894 0.500097 -0.242747 11.00000 0.02206 0.03352 =
0.02851 0.00243 0.00708 0.00466
EADP N1 N1'
EXYZ C17 C17'
EADP C17 C17'
SADI 0.020 N1 H1n N1 H2n
PART 1
C17 1 0.587389 0.334317 -0.317958 21.00000 0.02665 0.03376 =
0.03139 -0.00032 0.01032 0.00316
N1 3 0.523735 0.161639 -0.293646 21.00000 0.03822 0.02919 =
0.02703 -0.00317 0.01220 -0.00119
H1N 2 0.524334 0.047305 -0.333892 21.00000 -1.50000
H2N 2 0.529673 0.136056 -0.224847 21.00000 -1.50000
PART 2
C17' 1 0.587389 0.334317 -0.317958 -21.00000 0.02665 0.03376 =
0.03139 -0.00032 0.01032 0.00316
AFIX 43
H17' 2 0.544951 0.216043 -0.299207 -21.00000 -1.20000
AFIX 0
PART 0
C18 1 0.610263 0.348202 -0.421160 11.00000 0.03332 0.04347 =
0.02995 -0.00124 0.01192 0.00410
AFIX 43
H18 2 0.582957 0.237717 -0.472838 11.00000 -1.20000
AFIX 0
C19 1 0.671803 0.519726 -0.448963 11.00000 0.03315 0.05085 =
0.03324 0.01068 0.01338 0.00708
AFIX 43
H19 2 0.684295 0.527860 -0.520068 11.00000 -1.20000
AFIX 0
C20 1 0.715610 0.680421 -0.374074 11.00000 0.02740 0.04124 =
0.04563 0.01252 0.01397 0.00132
AFIX 43
H20 2 0.758757 0.797319 -0.393196 11.00000 -1.20000
AFIX 0
EXYZ C21 C21'
EADP c21 C21'
PARt 1
C21 1 0.695563 0.668017 -0.271107 21.00000 0.02246 0.03512 =
0.03706 0.00115 0.00750 0.00215
AFIX 43
H21 2 0.727532 0.775120 -0.218803 21.00000 -1.20000
AFIX 0
PART 2
C21' 1 0.695563 0.668017 -0.271107 -21.00000 0.02246 0.03512 =
0.03706 0.00115 0.00750 0.00215
N1' 3 0.732900 0.842548 -0.221935 -21.00000 0.03822 0.02919 =
0.02703 -0.00317 0.01220 -0.00119
AFIX 3
H1N' 2 0.720910 0.838867 -0.153753 -21.00000 -1.50000
H2N' 2 0.811935 0.857148 -0.217455 -21.00000 -1.50000
PARt 0
AFIX 0
HKLF 4
REM x13430 in P2(1)
REM R1 = 0.0318 for 2559 Fo > 4sig(Fo) and 0.0322 for all 2592 data
REM 238 parameters refined using 2 restraints
END
WGHT 0.0447 0.1902
REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, y-1/2, -z
HTAB C5 O3_$1
HTAB C7 O3_$1
HTAB C7 N1
EQIV $2 -x, y+1/2, -z
HTAB C15 O1_$2
HTAB N1 O3_$1
EQIV $3 -x+1, y+1/2, -z
HTAB N1' O1_$3
HTAB N1' O2_$3
REM Highest difference peak 0.177, deepest hole -0.139, 1-sigma level 0.030
Q1 1 0.1461 0.4193 0.0154 11.00000 0.05 0.18
Q2 1 0.0817 0.6892 -0.0983 11.00000 0.05 0.16
Q3 1 0.3347 0.4807 -0.1417 11.00000 0.05 0.15
Q4 1 0.5552 0.3951 -0.1219 11.00000 0.05 0.14
Q5 1 0.4995 0.4888 -0.0603 11.00000 0.05 0.14
Q6 1 0.6060 0.5041 -0.1935 11.00000 0.05 0.14
Q7 1 0.6999 0.5260 -0.2553 11.00000 0.05 0.13
Q8 1 0.6263 0.6355 -0.2609 11.00000 0.05 0.13
Q9 1 0.0776 0.4903 -0.0949 11.00000 0.05 0.13
Q10 1 0.5511 0.6019 -0.1200 11.00000 0.05 0.12
;
data_global
_journal_data_validation_number ?
_journal_date_recd_electronic 2018-09-12
_journal_date_accepted 2018-09-24
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2018
_journal_volume 74
_journal_issue 11
_journal_page_first 1543
_journal_page_last 1546
_journal_paper_category GO
_journal_paper_doi 10.1107/S2056989018013622
_journal_coeditor_code SJ5564
_publ_contact_author_name
;
Dr P.A. Crooks
;
_publ_contact_author_address
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
_publ_contact_author_email 'pacrooks@uams.edu'
_publ_contact_author_fax '501 686 6057'
_publ_contact_author_phone '501 686 6495'
_publ_section_title
;
Crystal structure of 13-(E)-(2-aminobenzylidene)parthenolide
;
_publ_section_title_footnote .
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Bommagani, Shobanbabu' .
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
'Penthala, Narsihma R.' .
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
'Parkin, Sean' .
;
Dept. of Chemistry
University of Kentucky
Lexington KY 40506
USA
;
'Crooks, Peter A.' .
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
_publ_section_synopsis
;
The title molecule is composed of fused ten-, five- (lactone), and
three-membered (epoxide) rings. The lactone ring shows a flattened
envelope-type conformation and bears a 2-aminobenzylidene substituent that is
disordered over two conformations. The ten-membered ring has an approximate
chair--chair conformation. There are no conventional hydrogen bonds, but
there are a number of weaker C---H...O-type interactions.
;