#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/21/2232157.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2232157
loop_
_publ_author_name
'Chen, Jian-Jun'
'Wang, Hai-Dong'
'Yao, Cheng'
_publ_section_title
;
 3-Methoxymethyl-16β,17β-epiestriol-16β,17β-diyl sulfate
;
_journal_coeditor_code           BQ2303
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2910
_journal_paper_doi               10.1107/S1600536811039213
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H26 O6 S'
_chemical_formula_moiety         'C20 H26 O6 S'
_chemical_formula_sum            'C20 H26 O6 S'
_chemical_formula_weight         394.47
_chemical_melting_point_gt       425
_chemical_melting_point_lt       426
_chemical_name_systematic
;
3-Methoxymethyl-16β,17β-epiestriol-16β,17β-diyl sulfate
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.296(2)
_cell_length_b                   23.503(5)
_cell_length_c                   7.9060(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     1913.1(7)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo,1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0602
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3875
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.73
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9415
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.174
_refine_ls_abs_structure_details 'Flack (1983), 1483 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0643
_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)+(0.1000P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1821
_reflns_number_gt                2174
_reflns_number_total             3530
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2303.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     P22ab
_cod_database_code               2232157
_cod_database_fobs_code          2232157
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S 0.28012(13) 0.68651(6) 0.51055(15) 0.0796(4) Uani d . 1 1
O O1 0.3963(3) 0.72326(15) 0.4438(4) 0.0812(9) Uani d . 1 1
C C1 0.4281(4) 0.8080(2) 0.2704(6) 0.0746(12) Uani d . 1 1
H H1A 0.4782 0.7802 0.2075 0.089 Uiso calc R 1 1
H H1B 0.4854 0.8383 0.3078 0.089 Uiso calc R 1 1
O O2 0.1693(3) 0.72213(15) 0.4266(4) 0.0780(9) Uani d . 1 1
C C2 0.3582(4) 0.7803(2) 0.4211(6) 0.0719(12) Uani d . 1 1
H H2A 0.3711 0.8024 0.5248 0.086 Uiso calc R 1 1
O O3 0.2689(5) 0.6907(2) 0.6849(4) 0.1299(16) Uani d . 1 1
C C3 0.2124(4) 0.7777(2) 0.3724(5) 0.0673(11) Uani d . 1 1
H H3B 0.1636 0.8076 0.4311 0.081 Uiso calc R 1 1
C C4 0.2067(4) 0.78685(18) 0.1763(5) 0.0635(10) Uani d . 1 1
O O4 0.2839(4) 0.63112(14) 0.4338(5) 0.1001(11) Uani d . 1 1
C C5 0.3156(4) 0.83170(18) 0.1630(6) 0.0606(11) Uani d . 1 1
H H5A 0.2838 0.8655 0.2228 0.073 Uiso calc R 1 1
O O5 0.2892(7) 0.9855(3) -0.7260(7) 0.155(2) Uani d . 1 1
C C6 0.0819(4) 0.8112(2) 0.1126(7) 0.0864(15) Uani d . 1 1
H H6A 0.0543 0.8420 0.1860 0.104 Uiso calc R 1 1
H H6B 0.0151 0.7821 0.1142 0.104 Uiso calc R 1 1
O O6 0.2753(9) 1.0346(3) -0.9382(11) 0.190(3) Uani d . 1 1
C C7 0.0990(5) 0.8339(3) -0.0709(7) 0.0858(15) Uani d . 1 1
H H7A 0.1155 0.8021 -0.1463 0.103 Uiso calc R 1 1
H H7B 0.0191 0.8521 -0.1069 0.103 Uiso calc R 1 1
C C8 0.2109(5) 0.87663(17) -0.0848(6) 0.0705(11) Uani d . 1 1
H H8A 0.1902 0.9082 -0.0084 0.085 Uiso calc R 1 1
C C9 0.3391(4) 0.85036(18) -0.0208(6) 0.0670(12) Uani d . 1 1
H H9A 0.3592 0.8167 -0.0891 0.080 Uiso calc R 1 1
C C10 0.2324(6) 0.90293(19) -0.2624(7) 0.0827(14) Uani d . 1 1
C C11 0.3484(7) 0.9168(2) -0.3227(8) 0.0948(18) Uani d . 1 1
C C12 0.4723(6) 0.9051(3) -0.2252(9) 0.1062(19) Uani d . 1 1
H H12A 0.5160 0.8727 -0.2753 0.127 Uiso calc R 1 1
H H12B 0.5294 0.9377 -0.2354 0.127 Uiso calc R 1 1
C C13 0.4483(5) 0.8932(2) -0.0402(7) 0.0838(15) Uani d . 1 1
H H13A 0.4254 0.9283 0.0173 0.101 Uiso calc R 1 1
H H13B 0.5268 0.8784 0.0112 0.101 Uiso calc R 1 1
C C14 0.1150(8) 0.9149(2) -0.3591(8) 0.104(2) Uani d . 1 1
H H14A 0.0322 0.9047 -0.3235 0.124 Uiso calc R 1 1
C C15 0.1424(10) 0.9461(3) -0.5261(9) 0.126(3) Uani d . 1 1
H H15A 0.0727 0.9564 -0.5945 0.151 Uiso calc R 1 1
C C16 0.2557(12) 0.9581(3) -0.5736(9) 0.120(3) Uani d . 1 1
C C17 0.3595(9) 0.9437(2) -0.4803(8) 0.110(2) Uani d . 1 1
H H17A 0.4420 0.9519 -0.5218 0.132 Uiso calc R 1 1
C C18 0.2327(12) 1.0332(4) -0.7645(12) 0.168(4) Uani d . 1 1
H H18A 0.2656 1.0650 -0.6991 0.202 Uiso calc R 1 1
H H18B 0.1389 1.0312 -0.7543 0.202 Uiso calc R 1 1
C C19 0.1688(12) 1.0446(4) -1.0307(14) 0.196(5) Uani d . 1 1
H H19A 0.1908 1.0437 -1.1487 0.294 Uiso calc R 1 1
H H19B 0.1342 1.0813 -1.0024 0.294 Uiso calc R 1 1
H H19C 0.1049 1.0159 -1.0073 0.294 Uiso calc R 1 1
C C20 0.2369(5) 0.73070(18) 0.0879(5) 0.0754(13) Uani d . 1 1
H H20A 0.2351 0.7362 -0.0324 0.113 Uiso calc R 1 1
H H20B 0.1732 0.7028 0.1191 0.113 Uiso calc R 1 1
H H20C 0.3216 0.7178 0.1213 0.113 Uiso calc R 1 1
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'
S S 0.1246 0.1234 '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
O3 S O4 119.2(3)
O3 S O2 108.8(3)
O4 S O2 109.0(2)
O3 S O1 111.0(3)
O4 S O1 109.7(2)
O2 S O1 96.84(17)
C2 O1 S 110.8(3)
C2 C1 C5 103.2(3)
C2 C1 H1A 111.1
C5 C1 H1A 111.1
C2 C1 H1B 111.1
C5 C1 H1B 111.1
H1A C1 H1B 109.1
C3 O2 S 112.7(3)
O1 C2 C1 111.9(4)
O1 C2 C3 105.3(4)
C1 C2 C3 106.1(4)
O1 C2 H2A 111.1
C1 C2 H2A 111.1
C3 C2 H2A 111.1
O2 C3 C2 105.0(4)
O2 C3 C4 114.0(4)
C2 C3 C4 106.0(4)
O2 C3 H3B 110.5
C2 C3 H3B 110.5
C4 C3 H3B 110.5
C6 C4 C20 110.6(4)
C6 C4 C5 109.9(4)
C20 C4 C5 114.3(4)
C6 C4 C3 114.7(4)
C20 C4 C3 109.1(4)
C5 C4 C3 97.7(3)
C9 C5 C1 120.4(4)
C9 C5 C4 111.9(3)
C1 C5 C4 105.2(3)
C9 C5 H5A 106.1
C1 C5 H5A 106.1
C4 C5 H5A 106.1
C18 O5 C16 119.0(8)
C4 C6 C7 110.4(4)
C4 C6 H6A 109.6
C7 C6 H6A 109.6
C4 C6 H6B 109.6
C7 C6 H6B 109.6
H6A C6 H6B 108.1
C19 O6 C18 106.0(9)
C8 C7 C6 112.2(4)
C8 C7 H7A 109.2
C6 C7 H7A 109.2
C8 C7 H7B 109.2
C6 C7 H7B 109.2
H7A C7 H7B 107.9
C7 C8 C9 110.9(4)
C7 C8 C10 115.7(4)
C9 C8 C10 109.6(4)
C7 C8 H8A 106.7
C9 C8 H8A 106.7
C10 C8 H8A 106.7
C13 C9 C5 113.7(4)
C13 C9 C8 109.6(4)
C5 C9 C8 106.9(3)
C13 C9 H9A 108.9
C5 C9 H9A 108.9
C8 C9 H9A 108.9
C11 C10 C14 120.7(6)
C11 C10 C8 123.5(5)
C14 C10 C8 115.7(5)
C10 C11 C17 120.2(7)
C10 C11 C12 122.0(6)
C17 C11 C12 117.7(7)
C13 C12 C11 112.9(5)
C13 C12 H12A 109.0
C11 C12 H12A 109.0
C13 C12 H12B 109.0
C11 C12 H12B 109.0
H12A C12 H12B 107.8
C12 C13 C9 110.0(4)
C12 C13 H13A 109.7
C9 C13 H13A 109.7
C12 C13 H13B 109.7
C9 C13 H13B 109.7
H13A C13 H13B 108.2
C10 C14 C15 113.0(7)
C10 C14 H14A 123.5
C15 C14 H14A 123.5
C16 C15 C14 122.2(8)
C16 C15 H15A 118.9
C14 C15 H15A 118.9
C15 C16 C17 121.2(8)
C15 C16 O5 125.8(10)
C17 C16 O5 112.9(9)
C16 C17 C11 122.5(8)
C16 C17 H17A 118.8
C11 C17 H17A 118.8
O5 C18 O6 96.1(10)
O5 C18 H18A 112.5
O6 C18 H18A 112.5
O5 C18 H18B 112.5
O6 C18 H18B 112.5
H18A C18 H18B 110.1
O6 C19 H19A 109.5
O6 C19 H19B 109.5
H19A C19 H19B 109.5
O6 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C4 C20 H20A 109.5
C4 C20 H20B 109.5
H20A C20 H20B 109.5
C4 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S O3 1.387(4)
S O4 1.437(4)
S O2 1.563(3)
S O1 1.567(3)
O1 C2 1.407(6)
C1 C2 1.537(7)
C1 C5 1.541(6)
C1 H1A 0.9700
C1 H1B 0.9700
O2 C3 1.444(6)
C2 C3 1.551(6)
C2 H2A 0.9800
C3 C4 1.567(6)
C3 H3B 0.9800
C4 C6 1.494(6)
C4 C20 1.526(6)
C4 C5 1.543(5)
C5 C9 1.537(6)
C5 H5A 0.9800
O5 C18 1.300(10)
O5 C16 1.410(9)
C6 C7 1.556(7)
C6 H6A 0.9700
C6 H6B 0.9700
O6 C19 1.339(11)
O6 C18 1.442(10)
C7 C8 1.532(6)
C7 H7A 0.9700
C7 H7B 0.9700
C8 C9 1.542(6)
C8 C10 1.550(7)
C8 H8A 0.9800
C9 C13 1.518(6)
C9 H9A 0.9800
C10 C11 1.326(8)
C10 C14 1.458(8)
C11 C17 1.402(8)
C11 C12 1.515(9)
C12 C13 1.510(8)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9700
C13 H13B 0.9700
C14 C15 1.536(10)
C14 H14A 0.9300
C15 C16 1.258(11)
C15 H15A 0.9300
C16 C17 1.342(11)
C17 H17A 0.9300
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
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
_geom_hbond_publ_flag
C20 H20A O3 1_554 0.96 2.50 3.338(5) 146 yes
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
O3 S O1 C2 -84.0(4)
O4 S O1 C2 142.3(3)
O2 S O1 C2 29.3(3)
O3 S O2 C3 98.6(4)
O4 S O2 C3 -129.9(3)
O1 S O2 C3 -16.4(3)
S O1 C2 C1 -146.1(3)
S O1 C2 C3 -31.3(4)
C5 C1 C2 O1 126.6(4)
C5 C1 C2 C3 12.3(4)
S O2 C3 C2 0.0(4)
S O2 C3 C4 115.6(3)
O1 C2 C3 O2 18.9(4)
C1 C2 C3 O2 137.6(4)
O1 C2 C3 C4 -102.1(4)
C1 C2 C3 C4 16.6(5)
O2 C3 C4 C6 90.8(5)
C2 C3 C4 C6 -154.2(4)
O2 C3 C4 C20 -33.9(5)
C2 C3 C4 C20 81.1(5)
O2 C3 C4 C5 -153.0(4)
C2 C3 C4 C5 -38.0(4)
C2 C1 C5 C9 -165.2(4)
C2 C1 C5 C4 -37.7(4)
C6 C4 C5 C9 -61.2(5)
C20 C4 C5 C9 63.9(5)
C3 C4 C5 C9 178.9(3)
C6 C4 C5 C1 166.4(4)
C20 C4 C5 C1 -68.6(4)
C3 C4 C5 C1 46.5(4)
C20 C4 C6 C7 -71.7(5)
C5 C4 C6 C7 55.5(5)
C3 C4 C6 C7 164.4(4)
C4 C6 C7 C8 -54.6(6)
C6 C7 C8 C9 56.2(6)
C6 C7 C8 C10 -178.2(4)
C1 C5 C9 C13 -54.0(5)
C4 C5 C9 C13 -178.3(4)
C1 C5 C9 C8 -175.0(3)
C4 C5 C9 C8 60.7(4)
C7 C8 C9 C13 178.7(4)
C10 C8 C9 C13 49.7(5)
C7 C8 C9 C5 -57.8(4)
C10 C8 C9 C5 173.3(3)
C7 C8 C10 C11 -146.2(5)
C9 C8 C10 C11 -19.9(6)
C7 C8 C10 C14 37.1(6)
C9 C8 C10 C14 163.4(4)
C14 C10 C11 C17 0.6(7)
C8 C10 C11 C17 -176.0(4)
C14 C10 C11 C12 179.8(5)
C8 C10 C11 C12 3.3(8)
C10 C11 C12 C13 -16.9(8)
C17 C11 C12 C13 162.4(4)
C11 C12 C13 C9 47.5(6)
C5 C9 C13 C12 175.0(4)
C8 C9 C13 C12 -65.5(5)
C11 C10 C14 C15 -2.4(7)
C8 C10 C14 C15 174.5(4)
C10 C14 C15 C16 1.9(9)
C14 C15 C16 C17 0.5(12)
C14 C15 C16 O5 178.7(5)
C18 O5 C16 C15 52.1(13)
C18 O5 C16 C17 -129.6(9)
C15 C16 C17 C11 -2.7(11)
O5 C16 C17 C11 179.0(5)
C10 C11 C17 C16 2.1(8)
C12 C11 C17 C16 -177.2(6)
C16 O5 C18 O6 -167.1(8)
C19 O6 C18 O5 130.1(10)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657091
