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#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/83/1548358.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1548358
loop_
_publ_author_name
'Mino R. Caira'
'Susan A. Bourne'
'Halima Samsodien'
_publ_section_title
;
 Thermal, X-ray Structural, and Dissolution Characteristics of Solid Forms
 Derived from the Anticancer Agents 2-Methoxyestradiol and
 2-Methoxyestradiol-3,17-O,O-Bis-Sulfamate
;
_journal_name_full               'Journal of Pharmaceutical Sciences'
_journal_page_first              3418
_journal_page_last               3425
_journal_paper_doi               10.1002/jps.24545
_journal_volume                  104
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H26 O3, 2(C1 H1 Cl3)'
_chemical_formula_sum            'C21 H28 Cl6 O3'
_chemical_formula_weight         541.13
_chemical_name_common            '2-methoxyestradiol chloroform solvate 1:2'
_chemical_name_systematic
; 
 17beta-2-methoxyestra-1,3,5(10)-triene-3,17-diol chloroform solvate 1:2'
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.386(2)
_cell_angle_beta                 95.464(2)
_cell_angle_gamma                107.774(2)
_cell_formula_units_Z            1
_cell_length_a                   6.3150(2)
_cell_length_b                   9.3352(3)
_cell_length_c                   11.1622(5)
_cell_measurement_reflns_used    1639
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      1.00
_cell_volume                     596.44(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean n/a
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       'phi- and omega-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17745
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         3.99
_diffrn_standards_decay_%        n/a
_diffrn_standards_interval_count n/a
_diffrn_standards_interval_time  n/a
_diffrn_standards_number         n/a
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  0.8780
_exptl_absorpt_correction_T_min  0.6137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.376
_refine_diff_density_rms         '0.055 '
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5178
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.1166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0715
_reflns_number_gt                4690
_reflns_number_total             5178
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jps24545-sup-0001-S1.CIF
_cod_data_source_block           2meclors
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-06-07
;
_cod_original_sg_symbol_H-M      P1
_cod_database_code               1548358
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7067(3) 0.3931(2) 0.31437(18) 0.0201(4) Uani 1 1 d . . .
H1 H 0.8627 0.4322 0.3513 0.024 Uiso 1 1 calc R . .
C2 C 0.6355(3) 0.4379(2) 0.21220(18) 0.0193(4) Uani 1 1 d . . .
C3 C 0.4071(3) 0.3805(2) 0.15639(18) 0.0197(4) Uani 1 1 d . . .
C4 C 0.2533(3) 0.2784(2) 0.20418(18) 0.0203(4) Uani 1 1 d . . .
H4 H 0.0976 0.2394 0.1665 0.024 Uiso 1 1 calc R . .
C5 C 0.3223(3) 0.2314(2) 0.30669(18) 0.0194(4) Uani 1 1 d . . .
C6 C 0.1430(3) 0.1197(2) 0.35258(19) 0.0213(4) Uani 1 1 d . . .
H6A H 0.0590 0.0254 0.2809 0.026 Uiso 1 1 calc R . .
H6B H 0.0341 0.1715 0.3817 0.026 Uiso 1 1 calc R . .
C7 C 0.2356(3) 0.0668(2) 0.45953(19) 0.0216(4) Uani 1 1 d . . .
H7A H 0.1137 0.0308 0.5061 0.026 Uiso 1 1 calc R . .
H7B H 0.2855 -0.0229 0.4237 0.026 Uiso 1 1 calc R . .
C8 C 0.4342(3) 0.2002(2) 0.55027(18) 0.0189(4) Uani 1 1 d . . .
H8 H 0.3863 0.2936 0.5805 0.023 Uiso 1 1 calc R . .
C9 C 0.6291(3) 0.2439(2) 0.47752(17) 0.0178(4) Uani 1 1 d . . .
H9 H 0.6644 0.1458 0.4435 0.021 Uiso 1 1 calc R . .
C10 C 0.5508(3) 0.2906(2) 0.36392(18) 0.0185(4) Uani 1 1 d . . .
C11 C 0.8475(3) 0.3661(2) 0.56251(18) 0.0209(4) Uani 1 1 d . . .
H11A H 0.9708 0.3787 0.5133 0.025 Uiso 1 1 calc R . .
H11B H 0.8249 0.4688 0.5903 0.025 Uiso 1 1 calc R . .
C12 C 0.9186(3) 0.3201(2) 0.67855(19) 0.0207(4) Uani 1 1 d . . .
H12A H 1.0529 0.4061 0.7334 0.025 Uiso 1 1 calc R . .
H12B H 0.9605 0.2246 0.6517 0.025 Uiso 1 1 calc R . .
C13 C 0.7256(3) 0.2881(2) 0.75268(18) 0.0194(4) Uani 1 1 d . . .
C14 C 0.5192(3) 0.1564(2) 0.66373(18) 0.0194(4) Uani 1 1 d . . .
H14 H 0.5705 0.0654 0.6301 0.023 Uiso 1 1 calc R . .
C15 C 0.3588(3) 0.1082(3) 0.75262(19) 0.0245(4) Uani 1 1 d . . .
H15A H 0.2530 -0.0011 0.7154 0.029 Uiso 1 1 calc R . .
H15B H 0.2704 0.1795 0.7721 0.029 Uiso 1 1 calc R . .
C16 C 0.5194(3) 0.1226(3) 0.8715(2) 0.0248(4) Uani 1 1 d . . .
H16A H 0.5077 0.0171 0.8789 0.030 Uiso 1 1 calc R . .
H16B H 0.4810 0.1821 0.9478 0.030 Uiso 1 1 calc R . .
C17 C 0.7614(3) 0.2110(2) 0.85604(18) 0.0220(4) Uani 1 1 d . . .
H17 H 0.8323 0.1307 0.8227 0.026 Uiso 1 1 calc R . .
C18 C 0.6775(4) 0.4397(2) 0.81035(19) 0.0232(4) Uani 1 1 d . . .
H18A H 0.6194 0.4755 0.7429 0.035 Uiso 1 1 calc R . .
H18B H 0.8177 0.5212 0.8608 0.035 Uiso 1 1 calc R . .
H18C H 0.5648 0.4191 0.8642 0.035 Uiso 1 1 calc R . .
O19 O 0.9030(2) 0.31600(18) 0.97253(13) 0.0250(3) Uani 1 1 d D . .
H19 H 0.827(5) 0.368(3) 1.006(3) 0.050(9) Uiso 1 1 d D . .
O20 O 0.7770(2) 0.53816(17) 0.15783(13) 0.0227(3) Uani 1 1 d . . .
C21 C 1.0034(3) 0.6243(3) 0.2256(2) 0.0250(4) Uani 1 1 d . . .
H21A H 0.9991 0.6842 0.3104 0.037 Uiso 1 1 calc R . .
H21B H 1.0823 0.6969 0.1812 0.037 Uiso 1 1 calc R . .
H21C H 1.0837 0.5508 0.2315 0.037 Uiso 1 1 calc R . .
O22 O 0.3491(2) 0.43133(18) 0.05729(13) 0.0239(3) Uani 1 1 d . . .
H22 H 0.2080 0.3944 0.0333 0.029 Uiso 1 1 calc R . .
C23 C 0.5669(4) 0.7883(3) 0.0403(2) 0.0293(5) Uani 1 1 d . . .
H23 H 0.5667 0.7048 0.0817 0.035 Uiso 1 1 calc R . .
Cl24 Cl 0.51919(9) 0.94405(6) 0.14857(5) 0.03463(14) Uani 1 1 d . . .
Cl25 Cl 0.83361(9) 0.85776(7) -0.00169(6) 0.03759(14) Uani 1 1 d . . .
Cl26 Cl 0.34963(10) 0.70686(7) -0.09321(6) 0.03866(15) Uani 1 1 d . . .
C27 C 0.5603(4) 0.6937(3) 0.5055(2) 0.0285(5) Uani 1 1 d . . .
H27 H 0.5540 0.5828 0.4693 0.034 Uiso 1 1 calc R . .
Cl28 Cl 0.59735(9) 0.78938(6) 0.38771(5) 0.03224(13) Uani 1 1 d . . .
Cl29 Cl 0.30417(9) 0.69046(7) 0.55753(6) 0.03767(15) Uani 1 1 d . . .
Cl30 Cl 0.78890(9) 0.78837(7) 0.63355(6) 0.03819(15) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C2 C1 C10 120.95(18) . .
C2 C1 H1 119.5 . .
C10 C1 H1 119.5 . .
O20 C2 C1 124.72(17) . .
O20 C2 C3 115.09(16) . .
C1 C2 C3 120.18(17) . .
O22 C3 C4 123.99(18) . .
O22 C3 C2 116.96(17) . .
C4 C3 C2 119.05(17) . .
C3 C4 C5 121.51(18) . .
C3 C4 H4 119.2 . .
C5 C4 H4 119.2 . .
C10 C5 C4 119.50(17) . .
C10 C5 C6 122.58(17) . .
C4 C5 C6 117.90(18) . .
C5 C6 C7 114.24(16) . .
C5 C6 H6A 108.7 . .
C7 C6 H6A 108.7 . .
C5 C6 H6B 108.7 . .
C7 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
C8 C7 C6 111.37(17) . .
C8 C7 H7A 109.4 . .
C6 C7 H7A 109.4 . .
C8 C7 H7B 109.4 . .
C6 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
C14 C8 C7 112.99(16) . .
C14 C8 C9 108.95(15) . .
C7 C8 C9 108.08(15) . .
C14 C8 H8 108.9 . .
C7 C8 H8 108.9 . .
C9 C8 H8 108.9 . .
C10 C9 C11 113.42(15) . .
C10 C9 C8 110.42(15) . .
C11 C9 C8 112.85(15) . .
C10 C9 H9 106.5 . .
C11 C9 H9 106.5 . .
C8 C9 H9 106.5 . .
C5 C10 C1 118.79(17) . .
C5 C10 C9 120.44(17) . .
C1 C10 C9 120.77(17) . .
C12 C11 C9 112.66(16) . .
C12 C11 H11A 109.1 . .
C9 C11 H11A 109.1 . .
C12 C11 H11B 109.1 . .
C9 C11 H11B 109.1 . .
H11A C11 H11B 107.8 . .
C11 C12 C13 110.76(16) . .
C11 C12 H12A 109.5 . .
C13 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
C13 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
C12 C13 C18 110.78(17) . .
C12 C13 C17 115.02(16) . .
C18 C13 C17 109.29(16) . .
C12 C13 C14 107.89(16) . .
C18 C13 C14 113.39(16) . .
C17 C13 C14 100.16(15) . .
C8 C14 C15 119.73(16) . .
C8 C14 C13 113.17(15) . .
C15 C14 C13 103.47(15) . .
C8 C14 H14 106.6 . .
C15 C14 H14 106.6 . .
C13 C14 H14 106.6 . .
C14 C15 C16 103.61(16) . .
C14 C15 H15A 111.0 . .
C16 C15 H15A 111.0 . .
C14 C15 H15B 111.0 . .
C16 C15 H15B 111.0 . .
H15A C15 H15B 109.0 . .
C15 C16 C17 106.34(16) . .
C15 C16 H16A 110.5 . .
C17 C16 H16A 110.5 . .
C15 C16 H16B 110.5 . .
C17 C16 H16B 110.5 . .
H16A C16 H16B 108.7 . .
O19 C17 C13 115.53(17) . .
O19 C17 C16 113.05(16) . .
C13 C17 C16 104.62(16) . .
O19 C17 H17 107.8 . .
C13 C17 H17 107.8 . .
C16 C17 H17 107.8 . .
C13 C18 H18A 109.5 . .
C13 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C13 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 O19 H19 106(2) . .
C2 O20 C21 117.21(15) . .
O20 C21 H21A 109.5 . .
O20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C3 O22 H22 109.5 . .
Cl26 C23 Cl25 111.02(12) . .
Cl26 C23 Cl24 110.15(13) . .
Cl25 C23 Cl24 109.70(12) . .
Cl26 C23 H23 108.6 . .
Cl25 C23 H23 108.6 . .
Cl24 C23 H23 108.6 . .
Cl28 C27 Cl30 110.54(12) . .
Cl28 C27 Cl29 110.38(13) . .
Cl30 C27 Cl29 109.88(12) . .
Cl28 C27 H27 108.7 . .
Cl30 C27 H27 108.7 . .
Cl29 C27 H27 108.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.390(3) .
C1 C10 1.408(3) .
C1 H1 0.9500 .
C2 O20 1.385(2) .
C2 C3 1.395(3) .
C3 O22 1.368(2) .
C3 C4 1.387(3) .
C4 C5 1.401(3) .
C4 H4 0.9500 .
C5 C10 1.399(3) .
C5 C6 1.512(3) .
C6 C7 1.532(3) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.525(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C14 1.524(3) .
C8 C9 1.546(3) .
C8 H8 1.0000 .
C9 C10 1.526(3) .
C9 C11 1.535(3) .
C9 H9 1.0000 .
C11 C12 1.532(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.533(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C18 1.535(3) .
C13 C17 1.537(3) .
C13 C14 1.538(3) .
C14 C15 1.532(3) .
C14 H14 1.0000 .
C15 C16 1.542(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 C17 1.548(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 O19 1.436(2) .
C17 H17 1.0000 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
O19 H19 0.838(10) .
O20 C21 1.433(2) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
O22 H22 0.8400 .
C23 Cl26 1.759(2) .
C23 Cl25 1.764(2) .
C23 Cl24 1.769(2) .
C23 H23 1.0000 .
C27 Cl28 1.759(2) .
C27 Cl30 1.763(2) .
C27 Cl29 1.764(2) .
C27 H27 1.0000 .
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
C10 C1 C2 O20 179.87(18) . . . .
C10 C1 C2 C3 -0.4(3) . . . .
O20 C2 C3 O22 -1.1(3) . . . .
C1 C2 C3 O22 179.14(17) . . . .
O20 C2 C3 C4 179.56(17) . . . .
C1 C2 C3 C4 -0.2(3) . . . .
O22 C3 C4 C5 -179.43(18) . . . .
C2 C3 C4 C5 -0.2(3) . . . .
C3 C4 C5 C10 1.1(3) . . . .
C3 C4 C5 C6 179.98(18) . . . .
C10 C5 C6 C7 -4.8(3) . . . .
C4 C5 C6 C7 176.43(17) . . . .
C5 C6 C7 C8 37.1(2) . . . .
C6 C7 C8 C14 175.42(16) . . . .
C6 C7 C8 C9 -63.9(2) . . . .
C14 C8 C9 C10 -179.27(15) . . . .
C7 C8 C9 C10 57.6(2) . . . .
C14 C8 C9 C11 -51.2(2) . . . .
C7 C8 C9 C11 -174.29(16) . . . .
C4 C5 C10 C1 -1.7(3) . . . .
C6 C5 C10 C1 179.51(18) . . . .
C4 C5 C10 C9 178.65(18) . . . .
C6 C5 C10 C9 -0.2(3) . . . .
C2 C1 C10 C5 1.4(3) . . . .
C2 C1 C10 C9 -178.96(18) . . . .
C11 C9 C10 C5 -154.48(17) . . . .
C8 C9 C10 C5 -26.7(2) . . . .
C11 C9 C10 C1 25.9(3) . . . .
C8 C9 C10 C1 153.66(18) . . . .
C10 C9 C11 C12 177.88(16) . . . .
C8 C9 C11 C12 51.4(2) . . . .
C9 C11 C12 C13 -54.8(2) . . . .
C11 C12 C13 C18 -66.6(2) . . . .
C11 C12 C13 C17 168.87(16) . . . .
C11 C12 C13 C14 58.1(2) . . . .
C7 C8 C14 C15 -60.0(2) . . . .
C9 C8 C14 C15 179.90(17) . . . .
C7 C8 C14 C13 177.62(16) . . . .
C9 C8 C14 C13 57.5(2) . . . .
C12 C13 C14 C8 -61.4(2) . . . .
C18 C13 C14 C8 61.6(2) . . . .
C17 C13 C14 C8 177.93(16) . . . .
C12 C13 C14 C15 167.47(16) . . . .
C18 C13 C14 C15 -69.5(2) . . . .
C17 C13 C14 C15 46.85(18) . . . .
C8 C14 C15 C16 -163.57(17) . . . .
C13 C14 C15 C16 -36.5(2) . . . .
C14 C15 C16 C17 11.8(2) . . . .
C12 C13 C17 O19 80.8(2) . . . .
C18 C13 C17 O19 -44.5(2) . . . .
C14 C13 C17 O19 -163.82(16) . . . .
C12 C13 C17 C16 -154.20(18) . . . .
C18 C13 C17 C16 80.5(2) . . . .
C14 C13 C17 C16 -38.86(19) . . . .
C15 C16 C17 O19 143.67(17) . . . .
C15 C16 C17 C13 17.2(2) . . . .
C1 C2 O20 C21 -12.3(3) . . . .
C3 C2 O20 C21 167.98(17) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139051534
