#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/07/2230744.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_2230744
loop_
_publ_author_name
'Asad, Mohammad'
'Oo, Chuan-Wei'
'Osman, Hasnah'
'Rosli, Mohd Mustaqim'
'Fun, Hoong-Kun'
_publ_section_title
;
 3-Hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(thiophen-3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one
;
_journal_coeditor_code           IS2734
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1813
_journal_paper_doi               10.1107/S160053681102407X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H26 O4 S'
_chemical_formula_moiety         'C21 H26 O4 S'
_chemical_formula_sum            'C21 H26 O4 S'
_chemical_formula_weight         374.48
_chemical_name_common
;
2,2'-(Thiophen-3-ylmethanetriyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
;
_chemical_name_systematic
;
3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)(thiophen-
3-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :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            32
_cell_length_a                   20.37700(10)
_cell_length_b                   20.37700(10)
_cell_length_c                   36.9066(7)
_cell_measurement_reflns_used    9719
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      29.91
_cell_measurement_theta_min      2.21
_cell_volume                     15324.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_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  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            162998
_diffrn_reflns_theta_full        30.19
_diffrn_reflns_theta_max         30.19
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9554
_exptl_absorpt_correction_T_min  0.9304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             6400
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.810
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     518
_refine_ls_number_reflns         11335
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+23.1894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1319
_reflns_number_gt                9435
_reflns_number_total             11335
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2734.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               2230744
_cod_database_fobs_code          2230744
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1A 0.26498(2) 0.53295(2) 0.064534(12) 0.02667(10) Uani d . 1 1 . .
O O1A 0.43198(5) 0.66891(5) 0.06947(3) 0.01577(19) Uani d . 1 1 . .
O O2A 0.32661(5) 0.79671(5) -0.01962(3) 0.0185(2) Uani d . 1 1 . .
O O3A 0.48148(5) 0.58783(5) 0.02392(3) 0.0160(2) Uani d . 1 1 . .
O O4A 0.38506(5) 0.71916(5) -0.06694(3) 0.0177(2) Uani d . 1 1 . .
C C1A 0.29441(7) 0.60778(7) 0.05155(4) 0.0174(3) Uani d . 1 1 . .
H H1AA 0.2849 0.6476 0.0639 0.021 Uiso calc R 1 1 . .
C C2A 0.30093(7) 0.49167(6) 0.03039(4) 0.0136(2) Uani d . 1 1 . .
H H2AA 0.2976 0.4458 0.0261 0.016 Uiso calc R 1 1 . .
C C3A 0.33798(7) 0.53824(7) 0.00845(4) 0.0184(3) Uani d . 1 1 . .
H H3AA 0.3627 0.5260 -0.0123 0.022 Uiso calc R 1 1 . .
C C4A 0.33333(6) 0.60401(7) 0.02128(4) 0.0140(2) Uani d . 1 1 . .
C C5A 0.36197(6) 0.66325(6) 0.00161(3) 0.0126(2) Uani d . 1 1 . .
H H5AA 0.3278 0.6755 -0.0166 0.015 Uiso calc R 1 1 . .
C C6A 0.36899(6) 0.72403(6) 0.02540(4) 0.0126(2) Uani d . 1 1 . .
C C7A 0.34849(7) 0.78460(7) 0.01386(4) 0.0143(2) Uani d . 1 1 . .
C C8A 0.34971(7) 0.84505(7) 0.03702(4) 0.0168(3) Uani d . 1 1 . .
H H8AA 0.3092 0.8706 0.0324 0.020 Uiso calc R 1 1 . .
H H8AB 0.3875 0.8725 0.0296 0.020 Uiso calc R 1 1 . .
C C9A 0.35486(7) 0.83136(7) 0.07775(4) 0.0139(2) Uani d . 1 1 . .
C C10A 0.40850(7) 0.77994(7) 0.08357(4) 0.0154(3) Uani d . 1 1 . .
H H10A 0.4517 0.8009 0.0794 0.018 Uiso calc R 1 1 . .
H H10B 0.4072 0.7655 0.1092 0.018 Uiso calc R 1 1 . .
C C11A 0.40332(6) 0.72029(7) 0.05960(4) 0.0129(2) Uani d . 1 1 . .
C C12A 0.42293(6) 0.64826(6) -0.02089(4) 0.0127(2) Uani d . 1 1 . .
C C13A 0.47480(7) 0.61050(6) -0.00969(4) 0.0133(2) Uani d . 1 1 . .
C C14A 0.53007(7) 0.59015(7) -0.03387(4) 0.0156(3) Uani d . 1 1 . .
H H14A 0.5414 0.5439 -0.0285 0.019 Uiso calc R 1 1 . .
H H14B 0.5690 0.6173 -0.0281 0.019 Uiso calc R 1 1 . .
C C15A 0.51536(7) 0.59647(7) -0.07442(4) 0.0142(2) Uani d . 1 1 . .
C C16A 0.48509(7) 0.66420(7) -0.08030(4) 0.0158(3) Uani d . 1 1 . .
H H16A 0.5192 0.6979 -0.0760 0.019 Uiso calc R 1 1 . .
H H16B 0.4710 0.6679 -0.1059 0.019 Uiso calc R 1 1 . .
C C17A 0.42705(7) 0.67870(7) -0.05621(4) 0.0141(2) Uani d . 1 1 . .
C C18A 0.57947(7) 0.59155(7) -0.09582(4) 0.0187(3) Uani d . 1 1 . .
H H18A 0.6093 0.6266 -0.0882 0.028 Uiso calc R 1 1 . .
H H18B 0.5702 0.5960 -0.1218 0.028 Uiso calc R 1 1 . .
H H18C 0.6000 0.5489 -0.0912 0.028 Uiso calc R 1 1 . .
C C19A 0.46737(7) 0.54295(7) -0.08661(4) 0.0192(3) Uani d . 1 1 . .
H H19A 0.4258 0.5480 -0.0736 0.029 Uiso calc R 1 1 . .
H H19B 0.4861 0.4997 -0.0813 0.029 Uiso calc R 1 1 . .
H H19C 0.4595 0.5470 -0.1127 0.029 Uiso calc R 1 1 . .
C C20A 0.28941(7) 0.80673(8) 0.09259(4) 0.0198(3) Uani d . 1 1 . .
H H20A 0.2775 0.7656 0.0805 0.030 Uiso calc R 1 1 . .
H H20B 0.2553 0.8397 0.0881 0.030 Uiso calc R 1 1 . .
H H20C 0.2934 0.7991 0.1187 0.030 Uiso calc R 1 1 . .
C C21A 0.37389(8) 0.89450(7) 0.09753(4) 0.0215(3) Uani d . 1 1 . .
H H21A 0.3757 0.8862 0.1237 0.032 Uiso calc R 1 1 . .
H H21B 0.3412 0.9286 0.0925 0.032 Uiso calc R 1 1 . .
H H21C 0.4170 0.9093 0.0891 0.032 Uiso calc R 1 1 . .
C C4B 0.81079(7) 0.38819(7) 0.03626(4) 0.0176(3) Uani d D 1 1 . .
C C1B 0.8193(3) 0.4552(2) 0.03293(13) 0.0218(9) Uani d PDU 0.735(3) 1 A 1
H H1BA 0.8443 0.4758 0.0144 0.026 Uiso calc PR 0.735(3) 1 A 1
S S1B 0.77821(9) 0.49656(7) 0.06707(4) 0.0299(3) Uani d PDU 0.735(3) 1 A 1
C C2B 0.7426(5) 0.4251(5) 0.0842(3) 0.0313(18) Uani d PDU 0.735(3) 1 A 1
H H2BA 0.7117 0.4229 0.1034 0.038 Uiso calc PR 0.735(3) 1 A 1
C C3B 0.7670(7) 0.3731(3) 0.0652(3) 0.0218(8) Uani d PDU 0.735(3) 1 A 1
H H3BA 0.7553 0.3292 0.0710 0.026 Uiso calc PR 0.735(3) 1 A 1
C C1Y 0.7673(19) 0.3684(9) 0.0634(10) 0.0218(9) Uani d PDU 0.265(3) 1 A 2
H H1YA 0.7542 0.3246 0.0683 0.026 Uiso calc PR 0.265(3) 1 A 2
S S1Y 0.7417(4) 0.4372(4) 0.0863(2) 0.0358(12) Uani d PDU 0.265(3) 1 A 2
C C2Y 0.7818(10) 0.4925(8) 0.0583(4) 0.037(4) Uani d PDU 0.265(3) 1 A 2
H H2YA 0.7763 0.5388 0.0574 0.044 Uiso calc PR 0.265(3) 1 A 2
C C3Y 0.8224(9) 0.4555(8) 0.0380(5) 0.0218(8) Uani d PDU 0.265(3) 1 A 2
H H3YA 0.8581 0.4747 0.0253 0.026 Uiso calc PR 0.265(3) 1 A 2
O O1B 0.84132(5) 0.30773(6) -0.06499(3) 0.0207(2) Uani d . 1 1 . .
O O2B 0.96238(5) 0.40881(5) 0.02813(3) 0.0183(2) Uani d . 1 1 . .
O O3B 0.81736(6) 0.20770(6) -0.02075(3) 0.0217(2) Uani d . 1 1 . .
O O4B 0.91887(5) 0.32452(5) 0.07410(3) 0.0181(2) Uani d . 1 1 . .
C C5B 0.83837(7) 0.33758(7) 0.00993(4) 0.0146(2) Uani d . 1 1 A .
H H5BA 0.8003 0.3258 -0.0059 0.018 Uiso calc R 1 1 . .
C C6B 0.88949(7) 0.36484(7) -0.01621(4) 0.0148(2) Uani d . 1 1 . .
C C7B 0.94425(7) 0.39922(7) -0.00606(4) 0.0149(2) Uani d . 1 1 A .
C C8B 0.98958(7) 0.43230(7) -0.03252(4) 0.0179(3) Uani d . 1 1 . .
H H8BA 1.0345 0.4324 -0.0223 0.021 Uiso calc R 1 1 A .
H H8BB 0.9757 0.4786 -0.0354 0.021 Uiso calc R 1 1 . .
C C9B 0.99160(7) 0.39999(7) -0.06994(4) 0.0180(3) Uani d . 1 1 A .
C C10B 0.92029(8) 0.38833(8) -0.08188(4) 0.0207(3) Uani d . 1 1 . .
H H10C 0.8989 0.4313 -0.0861 0.025 Uiso calc R 1 1 A .
H H10D 0.9203 0.3640 -0.1051 0.025 Uiso calc R 1 1 . .
C C11B 0.88085(7) 0.35024(7) -0.05431(4) 0.0168(3) Uani d . 1 1 A .
C C12B 0.85772(7) 0.27305(7) 0.02810(4) 0.0147(2) Uani d . 1 1 . .
C C13B 0.84358(7) 0.21397(7) 0.01210(4) 0.0168(3) Uani d . 1 1 A .
C C14B 0.85774(8) 0.14916(7) 0.02953(4) 0.0211(3) Uani d . 1 1 . .
H H14C 0.8991 0.1316 0.0193 0.025 Uiso calc R 1 1 A .
H H14D 0.8221 0.1181 0.0232 0.025 Uiso calc R 1 1 . .
C C15B 0.86403(7) 0.15195(7) 0.07086(4) 0.0181(3) Uani d . 1 1 A .
C C16B 0.90965(7) 0.20923(7) 0.08039(4) 0.0192(3) Uani d . 1 1 . .
H H16C 0.9072 0.2169 0.1068 0.023 Uiso calc R 1 1 A .
H H16D 0.9553 0.1962 0.0747 0.023 Uiso calc R 1 1 . .
C C17B 0.89507(7) 0.27293(7) 0.06126(4) 0.0150(2) Uani d . 1 1 A .
C C18B 0.89383(9) 0.08794(8) 0.08484(5) 0.0261(3) Uani d . 1 1 . .
H H18D 0.8993 0.0906 0.1112 0.039 Uiso calc R 1 1 A .
H H18E 0.9367 0.0809 0.0734 0.039 Uiso calc R 1 1 . .
H H18F 0.8646 0.0513 0.0789 0.039 Uiso calc R 1 1 . .
C C19B 0.79651(8) 0.16165(8) 0.08853(5) 0.0246(3) Uani d . 1 1 . .
H H19D 0.8014 0.1623 0.1149 0.037 Uiso calc R 1 1 A .
H H19E 0.7674 0.1255 0.0816 0.037 Uiso calc R 1 1 . .
H H19F 0.7776 0.2033 0.0804 0.037 Uiso calc R 1 1 . .
C C20B 1.02941(9) 0.33507(8) -0.06795(5) 0.0274(3) Uani d . 1 1 . .
H H20D 1.0754 0.3439 -0.0618 0.041 Uiso calc R 1 1 A .
H H20E 1.0272 0.3128 -0.0915 0.041 Uiso calc R 1 1 . .
H H20F 1.0099 0.3070 -0.0493 0.041 Uiso calc R 1 1 . .
C C21B 1.02532(9) 0.44528(8) -0.09711(4) 0.0243(3) Uani d . 1 1 . .
H H21D 1.0703 0.4541 -0.0891 0.036 Uiso calc R 1 1 A .
H H21E 1.0010 0.4867 -0.0988 0.036 Uiso calc R 1 1 . .
H H21F 1.0263 0.4241 -0.1210 0.036 Uiso calc R 1 1 . .
H H1A3 0.4580(12) 0.6109(13) 0.0393(7) 0.047(7) Uiso d . 1 1 . .
H H1B2 0.9381(13) 0.3845(13) 0.0434(7) 0.048(7) Uiso d . 1 1 . .
H H1B3 0.8215(12) 0.2413(13) -0.0329(7) 0.044(7) Uiso d . 1 1 . .
H H1A2 0.3405(12) 0.7665(13) -0.0342(7) 0.046(7) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A S1A C1A . . 94.78(7) ?
C7A O2A H1A2 . . 109.6(17) ?
C13A O3A H1A3 . . 111.2(17) ?
C4A C1A S1A . . 112.43(11) ?
C4A C1A H1AA . . 123.8 ?
S1A C1A H1AA . . 123.8 ?
C3A C2A S1A . . 108.42(10) ?
C3A C2A H2AA . . 125.8 ?
S1A C2A H2AA . . 125.8 ?
C4A C3A C2A . . 113.14(12) ?
C4A C3A H3AA . . 123.4 ?
C2A C3A H3AA . . 123.4 ?
C1A C4A C3A . . 111.21(12) ?
C1A C4A C5A . . 124.37(12) ?
C3A C4A C5A . . 124.13(12) ?
C6A C5A C4A . . 113.88(11) ?
C6A C5A C12A . . 113.57(11) ?
C4A C5A C12A . . 114.35(11) ?
C6A C5A H5AA . . 104.5 ?
C4A C5A H5AA . . 104.5 ?
C12A C5A H5AA . . 104.5 ?
C7A C6A C11A . . 117.78(12) ?
C7A C6A C5A . . 121.60(12) ?
C11A C6A C5A . . 120.37(11) ?
O2A C7A C6A . . 123.70(13) ?
O2A C7A C8A . . 112.39(12) ?
C6A C7A C8A . . 123.89(12) ?
C7A C8A C9A . . 114.25(11) ?
C7A C8A H8AA . . 108.7 ?
C9A C8A H8AA . . 108.7 ?
C7A C8A H8AB . . 108.7 ?
C9A C8A H8AB . . 108.7 ?
H8AA C8A H8AB . . 107.6 ?
C20A C9A C21A . . 109.09(12) ?
C20A C9A C10A . . 110.41(11) ?
C21A C9A C10A . . 109.16(12) ?
C20A C9A C8A . . 110.60(12) ?
C21A C9A C8A . . 109.41(11) ?
C10A C9A C8A . . 108.13(11) ?
C11A C10A C9A . . 114.85(11) ?
C11A C10A H10A . . 108.6 ?
C9A C10A H10A . . 108.6 ?
C11A C10A H10B . . 108.6 ?
C9A C10A H10B . . 108.6 ?
H10A C10A H10B . . 107.5 ?
O1A C11A C6A . . 121.57(12) ?
O1A C11A C10A . . 118.08(12) ?
C6A C11A C10A . . 120.27(12) ?
C13A C12A C17A . . 117.89(12) ?
C13A C12A C5A . . 125.17(12) ?
C17A C12A C5A . . 116.88(11) ?
O3A C13A C12A . . 123.70(12) ?
O3A C13A C14A . . 112.51(12) ?
C12A C13A C14A . . 123.79(12) ?
C13A C14A C15A . . 114.35(11) ?
C13A C14A H14A . . 108.7 ?
C15A C14A H14A . . 108.7 ?
C13A C14A H14B . . 108.7 ?
C15A C14A H14B . . 108.7 ?
H14A C14A H14B . . 107.6 ?
C16A C15A C18A . . 109.32(11) ?
C16A C15A C14A . . 107.09(11) ?
C18A C15A C14A . . 109.38(11) ?
C16A C15A C19A . . 110.11(12) ?
C18A C15A C19A . . 110.28(11) ?
C14A C15A C19A . . 110.60(12) ?
C17A C16A C15A . . 114.20(11) ?
C17A C16A H16A . . 108.7 ?
C15A C16A H16A . . 108.7 ?
C17A C16A H16B . . 108.7 ?
C15A C16A H16B . . 108.7 ?
H16A C16A H16B . . 107.6 ?
O4A C17A C12A . . 121.85(12) ?
O4A C17A C16A . . 118.57(12) ?
C12A C17A C16A . . 119.51(12) ?
C15A C18A H18A . . 109.5 ?
C15A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
C15A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
C15A C19A H19A . . 109.5 ?
C15A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
C15A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C9A C20A H20A . . 109.5 ?
C9A C20A H20B . . 109.5 ?
H20A C20A H20B . . 109.5 ?
C9A C20A H20C . . 109.5 ?
H20A C20A H20C . . 109.5 ?
H20B C20A H20C . . 109.5 ?
C9A C21A H21A . . 109.5 ?
C9A C21A H21B . . 109.5 ?
H21A C21A H21B . . 109.5 ?
C9A C21A H21C . . 109.5 ?
H21A C21A H21C . . 109.5 ?
H21B C21A H21C . . 109.5 ?
C1B C4B C1Y . . 115.4(9) ?
C3Y C4B C1Y . . 111.0(8) ?
C1B C4B C3B . . 111.0(3) ?
C3Y C4B C3B . . 106.5(9) ?
C1B C4B C5B . . 124.4(3) ?
C3Y C4B C5B . . 129.2(7) ?
C1Y C4B C5B . . 119.7(8) ?
C3B C4B C5B . . 124.2(3) ?
C4B C1B S1B . . 110.8(3) ?
C4B C1B H1BA . . 124.6 ?
S1B C1B H1BA . . 124.6 ?
C1B S1B C2B . . 93.4(4) ?
C3B C2B S1B . . 108.1(6) ?
C3B C2B H2BA . . 125.9 ?
S1B C2B H2BA . . 125.9 ?
C2B C3B C4B . . 116.4(6) ?
C2B C3B H3BA . . 121.8 ?
C4B C3B H3BA . . 121.8 ?
C4B C1Y S1Y . . 108.1(11) ?
C4B C1Y H1YA . . 126.0 ?
S1Y C1Y H1YA . . 126.0 ?
C1Y S1Y C2Y . . 95.3(9) ?
C3Y C2Y S1Y . . 104.9(12) ?
C3Y C2Y H2YA . . 127.5 ?
S1Y C2Y H2YA . . 127.5 ?
C2Y C3Y C4B . . 118.2(14) ?
C2Y C3Y H3YA . . 120.9 ?
C4B C3Y H3YA . . 120.9 ?
C7B O2B H1B2 . . 111.2(16) ?
C13B O3B H1B3 . . 112.0(18) ?
C4B C5B C6B . . 114.13(12) ?
C4B C5B C12B . . 113.43(11) ?
C6B C5B C12B . . 114.51(11) ?
C4B C5B H5BA . . 104.4 ?
C6B C5B H5BA . . 104.4 ?
C12B C5B H5BA . . 104.4 ?
C7B C6B C11B . . 118.01(13) ?
C7B C6B C5B . . 124.75(12) ?
C11B C6B C5B . . 117.17(12) ?
O2B C7B C6B . . 124.14(13) ?
O2B C7B C8B . . 112.32(12) ?
C6B C7B C8B . . 123.51(12) ?
C7B C8B C9B . . 114.18(12) ?
C7B C8B H8BA . . 108.7 ?
C9B C8B H8BA . . 108.7 ?
C7B C8B H8BB . . 108.7 ?
C9B C8B H8BB . . 108.7 ?
H8BA C8B H8BB . . 107.6 ?
C21B C9B C8B . . 110.18(12) ?
C21B C9B C20B . . 109.09(13) ?
C8B C9B C20B . . 109.97(13) ?
C21B C9B C10B . . 109.31(13) ?
C8B C9B C10B . . 107.45(12) ?
C20B C9B C10B . . 110.83(13) ?
C11B C10B C9B . . 112.90(12) ?
C11B C10B H10C . . 109.0 ?
C9B C10B H10C . . 109.0 ?
C11B C10B H10D . . 109.0 ?
C9B C10B H10D . . 109.0 ?
H10C C10B H10D . . 107.8 ?
O1B C11B C6B . . 121.90(13) ?
O1B C11B C10B . . 119.18(13) ?
C6B C11B C10B . . 118.92(12) ?
C13B C12B C17B . . 118.36(13) ?
C13B C12B C5B . . 120.82(12) ?
C17B C12B C5B . . 120.69(12) ?
O3B C13B C12B . . 124.10(14) ?
O3B C13B C14B . . 112.59(13) ?
C12B C13B C14B . . 123.29(13) ?
C13B C14B C15B . . 114.29(12) ?
C13B C14B H14C . . 108.7 ?
C15B C14B H14C . . 108.7 ?
C13B C14B H14D . . 108.7 ?
C15B C14B H14D . . 108.7 ?
H14C C14B H14D . . 107.6 ?
C18B C15B C14B . . 109.73(13) ?
C18B C15B C16B . . 109.35(13) ?
C14B C15B C16B . . 107.90(12) ?
C18B C15B C19B . . 108.82(12) ?
C14B C15B C19B . . 110.66(13) ?
C16B C15B C19B . . 110.36(12) ?
C17B C16B C15B . . 115.39(12) ?
C17B C16B H16C . . 108.4 ?
C15B C16B H16C . . 108.4 ?
C17B C16B H16D . . 108.4 ?
C15B C16B H16D . . 108.4 ?
H16C C16B H16D . . 107.5 ?
O4B C17B C12B . . 121.67(13) ?
O4B C17B C16B . . 118.02(12) ?
C12B C17B C16B . . 120.22(12) ?
C15B C18B H18D . . 109.5 ?
C15B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
C15B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
C15B C19B H19D . . 109.5 ?
C15B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
C15B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
C9B C20B H20D . . 109.5 ?
C9B C20B H20E . . 109.5 ?
H20D C20B H20E . . 109.5 ?
C9B C20B H20F . . 109.5 ?
H20D C20B H20F . . 109.5 ?
H20E C20B H20F . . 109.5 ?
C9B C21B H21D . . 109.5 ?
C9B C21B H21E . . 109.5 ?
H21D C21B H21E . . 109.5 ?
C9B C21B H21F . . 109.5 ?
H21D C21B H21F . . 109.5 ?
H21E C21B H21F . . 109.5 ?
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
S1A C2A . 1.6829(14) ?
S1A C1A . 1.7071(15) ?
O1A C11A . 1.2530(16) ?
O2A C7A . 1.3368(16) ?
O2A H1A2 . 0.87(3) ?
O3A C13A . 1.3308(16) ?
O3A H1A3 . 0.88(3) ?
O4A C17A . 1.2524(17) ?
C1A C4A . 1.3722(19) ?
C1A H1AA . 0.9500 ?
C2A C3A . 1.458(2) ?
C2A H2AA . 0.9500 ?
C3A C4A . 1.4246(19) ?
C3A H3AA . 0.9500 ?
C4A C5A . 1.5249(18) ?
C5A C6A . 1.5247(18) ?
C5A C12A . 1.5252(18) ?
C5A H5AA . 1.0000 ?
C6A C7A . 1.3708(18) ?
C6A C11A . 1.4452(18) ?
C7A C8A . 1.4995(19) ?
C8A C9A . 1.5323(19) ?
C8A H8AA . 0.9900 ?
C8A H8AB . 0.9900 ?
C9A C20A . 1.5265(19) ?
C9A C21A . 1.5293(19) ?
C9A C10A . 1.5293(19) ?
C10A C11A . 1.5069(19) ?
C10A H10A . 0.9900 ?
C10A H10B . 0.9900 ?
C12A C13A . 1.3711(18) ?
C12A C17A . 1.4459(18) ?
C13A C14A . 1.4956(19) ?
C14A C15A . 1.5317(19) ?
C14A H14A . 0.9900 ?
C14A H14B . 0.9900 ?
C15A C16A . 1.5272(19) ?
C15A C18A . 1.5298(19) ?
C15A C19A . 1.5324(19) ?
C16A C17A . 1.5087(19) ?
C16A H16A . 0.9900 ?
C16A H16B . 0.9900 ?
C18A H18A . 0.9800 ?
C18A H18B . 0.9800 ?
C18A H18C . 0.9800 ?
C19A H19A . 0.9800 ?
C19A H19B . 0.9800 ?
C19A H19C . 0.9800 ?
C20A H20A . 0.9800 ?
C20A H20B . 0.9800 ?
C20A H20C . 0.9800 ?
C21A H21A . 0.9800 ?
C21A H21B . 0.9800 ?
C21A H21C . 0.9800 ?
C4B C1B . 1.382(5) ?
C4B C3Y . 1.393(16) ?
C4B C1Y . 1.396(18) ?
C4B C3B . 1.426(6) ?
C4B C5B . 1.5244(19) ?
C1B S1B . 1.732(6) ?
C1B H1BA . 0.9500 ?
S1B C2B . 1.745(9) ?
C2B C3B . 1.364(11) ?
C2B H2BA . 0.9500 ?
C3B H3BA . 0.9500 ?
C1Y S1Y . 1.718(19) ?
C1Y H1YA . 0.9500 ?
S1Y C2Y . 1.734(14) ?
C2Y C3Y . 1.346(19) ?
C2Y H2YA . 0.9500 ?
C3Y H3YA . 0.9500 ?
O1B C11B . 1.2467(18) ?
O2B C7B . 1.3291(16) ?
O2B H1B2 . 0.90(3) ?
O3B C13B . 1.3309(18) ?
O3B H1B3 . 0.82(3) ?
O4B C17B . 1.2510(17) ?
C5B C6B . 1.5245(19) ?
C5B C12B . 1.5278(19) ?
C5B H5BA . 1.0000 ?
C6B C7B . 1.3699(19) ?
C6B C11B . 1.4481(19) ?
C7B C8B . 1.504(2) ?
C8B C9B . 1.531(2) ?
C8B H8BA . 0.9900 ?
C8B H8BB . 0.9900 ?
C9B C21B . 1.526(2) ?
C9B C20B . 1.533(2) ?
C9B C10B . 1.537(2) ?
C10B C11B . 1.511(2) ?
C10B H10C . 0.9900 ?
C10B H10D . 0.9900 ?
C12B C13B . 1.3715(19) ?
C12B C17B . 1.4414(19) ?
C13B C14B . 1.497(2) ?
C14B C15B . 1.532(2) ?
C14B H14C . 0.9900 ?
C14B H14D . 0.9900 ?
C15B C18B . 1.528(2) ?
C15B C16B . 1.533(2) ?
C15B C19B . 1.535(2) ?
C16B C17B . 1.507(2) ?
C16B H16C . 0.9900 ?
C16B H16D . 0.9900 ?
C18B H18D . 0.9800 ?
C18B H18E . 0.9800 ?
C18B H18F . 0.9800 ?
C19B H19D . 0.9800 ?
C19B H19E . 0.9800 ?
C19B H19F . 0.9800 ?
C20B H20D . 0.9800 ?
C20B H20E . 0.9800 ?
C20B H20F . 0.9800 ?
C21B H21D . 0.9800 ?
C21B H21E . 0.9800 ?
C21B H21F . 0.9800 ?
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
O3A H1A3 O1A . 0.88(3) 1.71(3) 2.5638(15) 164(2) yes
O2B H1B2 O4B . 0.90(3) 1.71(3) 2.5719(15) 159(3) yes
O3B H1B3 O1B . 0.82(3) 1.84(3) 2.6569(17) 170(3) yes
O2A H1A2 O4A . 0.87(3) 1.79(3) 2.6393(15) 165(2) yes
C10A H10A O1A 6_564 0.99 2.48 3.4530(18) 169 yes
C16B H16D O4B 6_654 0.99 2.60 3.5688(18) 167 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2A S1A C1A C4A . . . . -1.00(12) ?
C1A S1A C2A C3A . . . . 0.84(11) ?
S1A C2A C3A C4A . . . . -0.53(15) ?
S1A C1A C4A C3A . . . . 0.82(16) ?
S1A C1A C4A C5A . . . . 174.82(10) ?
C2A C3A C4A C1A . . . . -0.19(17) ?
C2A C3A C4A C5A . . . . -174.20(12) ?
C1A C4A C5A C6A . . . . 24.20(18) ?
C3A C4A C5A C6A . . . . -162.57(13) ?
C1A C4A C5A C12A . . . . 157.06(13) ?
C3A C4A C5A C12A . . . . -29.70(18) ?
C4A C5A C6A C7A . . . . -133.08(13) ?
C12A C5A C6A C7A . . . . 93.68(15) ?
C4A C5A C6A C11A . . . . 52.79(16) ?
C12A C5A C6A C11A . . . . -80.45(15) ?
C11A C6A C7A O2A . . . . 168.04(12) ?
C5A C6A C7A O2A . . . . -6.2(2) ?
C11A C6A C7A C8A . . . . -10.3(2) ?
C5A C6A C7A C8A . . . . 175.43(12) ?
O2A C7A C8A C9A . . . . 163.14(12) ?
C6A C7A C8A C9A . . . . -18.4(2) ?
C7A C8A C9A C20A . . . . -74.73(15) ?
C7A C8A C9A C21A . . . . 165.07(12) ?
C7A C8A C9A C10A . . . . 46.28(16) ?
C20A C9A C10A C11A . . . . 72.02(15) ?
C21A C9A C10A C11A . . . . -168.06(12) ?
C8A C9A C10A C11A . . . . -49.11(15) ?
C7A C6A C11A O1A . . . . -169.28(12) ?
C5A C6A C11A O1A . . . . 5.06(19) ?
C7A C6A C11A C10A . . . . 7.43(19) ?
C5A C6A C11A C10A . . . . -178.22(12) ?
C9A C10A C11A O1A . . . . -159.26(12) ?
C9A C10A C11A C6A . . . . 23.91(18) ?
C6A C5A C12A C13A . . . . 88.43(16) ?
C4A C5A C12A C13A . . . . -44.59(18) ?
C6A C5A C12A C17A . . . . -88.90(14) ?
C4A C5A C12A C17A . . . . 138.08(12) ?
C17A C12A C13A O3A . . . . 169.83(12) ?
C5A C12A C13A O3A . . . . -7.5(2) ?
C17A C12A C13A C14A . . . . -10.3(2) ?
C5A C12A C13A C14A . . . . 172.44(12) ?
O3A C13A C14A C15A . . . . 162.39(11) ?
C12A C13A C14A C15A . . . . -17.53(19) ?
C13A C14A C15A C16A . . . . 47.25(15) ?
C13A C14A C15A C18A . . . . 165.61(12) ?
C13A C14A C15A C19A . . . . -72.74(15) ?
C18A C15A C16A C17A . . . . -171.28(11) ?
C14A C15A C16A C17A . . . . -52.88(15) ?
C19A C15A C16A C17A . . . . 67.43(15) ?
C13A C12A C17A O4A . . . . -172.58(13) ?
C5A C12A C17A O4A . . . . 4.95(19) ?
C13A C12A C17A C16A . . . . 4.36(19) ?
C5A C12A C17A C16A . . . . -178.12(11) ?
C15A C16A C17A O4A . . . . -153.95(12) ?
C15A C16A C17A C12A . . . . 29.01(17) ?
C3Y C4B C1B S1B . . . . -54(7) ?
C1Y C4B C1B S1B . . . . 6(3) ?
C3B C4B C1B S1B . . . . 4.1(7) ?
C5B C4B C1B S1B . . . . 177.77(17) ?
C4B C1B S1B C2B . . . . -5.0(5) ?
C1B S1B C2B C3B . . . . 4.4(11) ?
S1B C2B C3B C4B . . . . -2.9(17) ?
C1B C4B C3B C2B . . . . -0.8(15) ?
C3Y C4B C3B C2B . . . . 6(2) ?
C1Y C4B C3B C2B . . . . -16E1(4) ?
C5B C4B C3B C2B . . . . -174.5(9) ?
C1B C4B C1Y S1Y . . . . -4(4) ?
C3Y C4B C1Y S1Y . . . . 4(3) ?
C3B C4B C1Y S1Y . . . . 1E1(3) ?
C5B C4B C1Y S1Y . . . . -176.2(13) ?
C4B C1Y S1Y C2Y . . . . 5(3) ?
C1Y S1Y C2Y C3Y . . . . -12(3) ?
S1Y C2Y C3Y C4B . . . . 17(2) ?
C1B C4B C3Y C2Y . . . . 109(7) ?
C1Y C4B C3Y C2Y . . . . -15(2) ?
C3B C4B C3Y C2Y . . . . -15(2) ?
C5B C4B C3Y C2Y . . . . 165.4(12) ?
C1B C4B C5B C6B . . . . 13.1(3) ?
C3Y C4B C5B C6B . . . . 4.8(10) ?
C1Y C4B C5B C6B . . . . -175(2) ?
C3B C4B C5B C6B . . . . -174.1(8) ?
C1B C4B C5B C12B . . . . 146.7(3) ?
C3Y C4B C5B C12B . . . . 138.4(10) ?
C1Y C4B C5B C12B . . . . -42(2) ?
C3B C4B C5B C12B . . . . -40.5(9) ?
C4B C5B C6B C7B . . . . 52.84(18) ?
C12B C5B C6B C7B . . . . -80.25(17) ?
C4B C5B C6B C11B . . . . -130.44(13) ?
C12B C5B C6B C11B . . . . 96.47(15) ?
C11B C6B C7B O2B . . . . -171.28(13) ?
C5B C6B C7B O2B . . . . 5.4(2) ?
C11B C6B C7B C8B . . . . 10.8(2) ?
C5B C6B C7B C8B . . . . -172.53(13) ?
O2B C7B C8B C9B . . . . 153.75(12) ?
C6B C7B C8B C9B . . . . -28.1(2) ?
C7B C8B C9B C21B . . . . 166.61(13) ?
C7B C8B C9B C20B . . . . -73.10(16) ?
C7B C8B C9B C10B . . . . 47.61(16) ?
C21B C9B C10B C11B . . . . -173.48(12) ?
C8B C9B C10B C11B . . . . -53.92(16) ?
C20B C9B C10B C11B . . . . 66.25(16) ?
C7B C6B C11B O1B . . . . 163.83(14) ?
C5B C6B C11B O1B . . . . -13.1(2) ?
C7B C6B C11B C10B . . . . -17.0(2) ?
C5B C6B C11B C10B . . . . 166.05(13) ?
C9B C10B C11B O1B . . . . -140.33(14) ?
C9B C10B C11B C6B . . . . 40.48(18) ?
C4B C5B C12B C13B . . . . 138.17(13) ?
C6B C5B C12B C13B . . . . -88.41(16) ?
C4B C5B C12B C17B . . . . -45.95(17) ?
C6B C5B C12B C17B . . . . 87.47(15) ?
C17B C12B C13B O3B . . . . -170.66(13) ?
C5B C12B C13B O3B . . . . 5.3(2) ?
C17B C12B C13B C14B . . . . 7.7(2) ?
C5B C12B C13B C14B . . . . -176.31(13) ?
O3B C13B C14B C15B . . . . -159.09(13) ?
C12B C13B C14B C15B . . . . 22.4(2) ?
C13B C14B C15B C18B . . . . -166.86(13) ?
C13B C14B C15B C16B . . . . -47.79(17) ?
C13B C14B C15B C19B . . . . 73.04(16) ?
C18B C15B C16B C17B . . . . 166.62(13) ?
C14B C15B C16B C17B . . . . 47.31(17) ?
C19B C15B C16B C17B . . . . -73.70(16) ?
C13B C12B C17B O4B . . . . 168.08(13) ?
C5B C12B C17B O4B . . . . -7.9(2) ?
C13B C12B C17B C16B . . . . -8.5(2) ?
C5B C12B C17B C16B . . . . 175.52(12) ?
C15B C16B C17B O4B . . . . 162.45(13) ?
C15B C16B C17B C12B . . . . -20.85(19) ?
