#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:21:51 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286185 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/95/7159517.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_7159517
loop_
_publ_author_name
'Wang, Xilong'
'Luo, Yu'
'Zhao, Jiaji'
'Luo, Shuang'
_publ_section_title
;
 CPA-catalyzed asymmetric domino thia-Michael/aldol reactions for
 simultaneous chiral center and axial chirality formation.
;
_journal_issue                   33
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6697
_journal_page_last               6701
_journal_paper_doi               10.1039/d3ob01087b
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H18 O2 S'
_chemical_formula_sum            'C23 H18 O2 S'
_chemical_formula_weight         358.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc27l1b7
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-03-25 deposited with the CCDC.	2023-08-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4430(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.36850(10)
_cell_length_b                   10.75200(10)
_cell_length_c                   15.87320(10)
_cell_measurement_reflns_used    26328
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      76.8590
_cell_measurement_theta_min      2.8040
_cell_volume                     1745.60(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00   9.00   0.50    0.05    --  -46.62 103.00 124.00  184
  2  ω     -5.00  83.00   0.50    0.05    --   46.62-103.00  22.00  176
  3  ω   -110.00 -27.00   0.50    0.05    -- -100.00 103.00 124.00  166
  4  ω     34.00 110.00   0.50    0.05    --  107.00-103.00  22.00  152
  5  ω     86.00 178.00   0.50    0.05    --  107.00 103.00 124.00  184
  6  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00 150.00   96
  7  ω    -63.00  26.00   0.50    0.05    --  -46.62  57.00  90.00  178
  8  ω   -119.00 -71.00   0.50    0.05    --  -46.62-125.00-180.00   96
  9  ω   -119.00 -23.00   0.50    0.05    --  -46.62 -77.00 -30.00  192
 10  ω    -62.00  29.00   0.50    0.05    --  -46.62  19.00-120.00  182
 11  ω     15.00  95.00   0.50    0.05    --   46.62-125.00-150.00  160
 12  ω   -115.00 -25.00   0.50    0.05    -- -100.00  30.00   0.00  180
 13  ω   -117.00 -27.00   0.50    0.05    -- -100.00 125.00 -90.00  180
 14  ω   -115.00 -25.00   0.50    0.05    -- -100.00  30.00 150.00  180
 15  ω   -124.00 -27.00   0.50    0.05    -- -100.00  77.00 120.00  194
 16  ω   -173.00 -82.00   0.50    0.05    -- -100.00 -61.00 -60.00  182
 17  ω   -173.00 -82.00   0.50    0.05    -- -100.00-103.00  22.00  182
 18  ω     34.00 125.00   0.50    0.05    --  107.00 -61.00  30.00  182
 19  ω     93.00 178.00   0.50    0.05    --  107.00  45.00-120.00  170
 20  ω     34.00 117.00   0.50    0.05    --  107.00-125.00  90.00  166
 21  ω     76.00 178.00   0.50    0.05    --  107.00 125.00 -30.00  204
 22  ω     34.00 117.00   0.50    0.05    --  107.00-125.00-120.00  166
 23  ω     34.00 125.00   0.50    0.05    --  107.00 -61.00-180.00  182
 24  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 120.00  150
 25  ω     90.00 178.00   0.50    0.05    --  107.00  61.00 150.00  176
 26  ω     34.00 117.00   0.50    0.05    --  107.00-125.00 -30.00  166
 27  ω     92.00 178.00   0.50    0.05    --  107.00  30.00-150.00  172
 28  ω     89.00 178.00   0.50    0.05    --  107.00  15.00 -60.00  178
 29  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 -90.00  150
 30  ω     93.00 178.00   0.50    0.05    --  107.00  45.00 120.00  170
 31  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 150.00  150
 32  ω     34.00 109.00   0.50    0.05    --  107.00 -94.00 -60.00  150
 33  ω     34.00 117.00   0.50    0.05    --  107.00-125.00   0.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1417286000
_diffrn_orient_matrix_UB_12      0.0396470000
_diffrn_orient_matrix_UB_13      0.0341516000
_diffrn_orient_matrix_UB_21      -0.0480479000
_diffrn_orient_matrix_UB_22      0.1316157000
_diffrn_orient_matrix_UB_23      0.0175730000
_diffrn_orient_matrix_UB_31      -0.0172944000
_diffrn_orient_matrix_UB_32      -0.0404715000
_diffrn_orient_matrix_UB_33      0.0905542000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35186
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.042
_diffrn_reflns_theta_min         2.822
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 3207 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(15)
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         7207
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+0.6378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1008
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                7061
_reflns_number_total             7207
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01087b2.cif
_cod_data_source_block           fanwx_98_200922
_cod_depositor_comments          'Adding full bibliography for 7159517.cif.'
_cod_database_code               7159517
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHOS
_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_max   0.668
_shelx_estimated_absorpt_t_min   0.621
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23), C35(H35), C49(H49), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C47(H47), C15(H15), C41(H41), C21(H21), C32(H32), C31(H31), C29(H29),
 C39(H39), C5(H5), C20(H20), C40(H40), C38(H38), C44(H44), C30(H30), C45(H45),
 C46(H46), C12(H12), C19(H19), C18(H18), C14(H14), C4(H4), C6(H6), C13(H13)
2.c Idealised Me refined as rotating group:
 C52(H52A,H52B,H52C), C26(H26A,H26B,H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O24(H24), O50(H50)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.781
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_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
S1 S 1.20826(7) 0.15591(6) 0.51597(4) 0.02066(16) Uani 1 1 d . . . . .
S27 S 0.41489(6) 0.93435(6) 0.09073(4) 0.02020(16) Uani 1 1 d . . . . .
O24 O 0.8384(2) 0.3405(2) 0.37510(14) 0.0246(5) Uani 1 1 d . . . . .
H24 H 0.870033 0.397174 0.350548 0.037 Uiso 1 1 calc R U . . .
O51 O 0.2967(2) 0.5340(2) 0.04431(14) 0.0261(5) Uani 1 1 d . . . . .
O25 O 1.0374(2) 0.4851(2) 0.34270(14) 0.0245(5) Uani 1 1 d . . . . .
O50 O 0.2541(2) 0.6423(2) -0.11008(13) 0.0237(4) Uani 1 1 d . . . . .
H50 H 0.249940 0.586273 -0.075624 0.036 Uiso 1 1 calc R U . . .
C2 C 1.1227(3) 0.1220(3) 0.41277(18) 0.0193(6) Uani 1 1 d . . . . .
C28 C 0.2547(3) 0.9189(3) 0.03218(17) 0.0204(6) Uani 1 1 d . . . . .
C3 C 1.1800(3) 0.0329(3) 0.36635(19) 0.0223(6) Uani 1 1 d . . . . .
H3 H 1.258071 -0.004878 0.390457 0.027 Uiso 1 1 calc R U . . .
C33 C 0.2168(3) 0.8323(3) -0.03391(17) 0.0192(6) Uani 1 1 d . . . . .
C47 C 0.7477(3) 0.7803(3) 0.0898(2) 0.0239(6) Uani 1 1 d . . . . .
H47 H 0.757536 0.824772 0.041024 0.029 Uiso 1 1 calc R U . . .
C15 C 1.4780(3) 0.3840(3) 0.4198(2) 0.0265(6) Uani 1 1 d . . . . .
H15 H 1.552987 0.386133 0.460904 0.032 Uiso 1 1 calc R U . . .
C43 C 0.6081(3) 0.7015(3) 0.18607(18) 0.0202(6) Uani 1 1 d . . . . .
C17 C 1.3512(3) 0.4365(3) 0.53519(18) 0.0211(5) Uani 1 1 d . . . . .
C22 C 1.2540(3) 0.3934(3) 0.58040(18) 0.0204(6) Uani 1 1 d . . . . .
C41 C 0.4748(3) 0.7136(3) 0.30243(19) 0.0247(6) Uani 1 1 d . . . . .
H41 H 0.551671 0.730050 0.339953 0.030 Uiso 1 1 calc R U . . .
C16 C 1.3557(3) 0.4021(3) 0.44496(19) 0.0218(6) Uani 1 1 d . . . . .
C7 C 1.0040(3) 0.1786(3) 0.37766(18) 0.0187(5) Uani 1 1 d . . . . .
C21 C 1.2583(3) 0.4302(3) 0.66514(18) 0.0236(6) Uani 1 1 d . . . . .
H21 H 1.193871 0.402365 0.695006 0.028 Uiso 1 1 calc R U . . .
C23 C 1.1441(3) 0.3088(3) 0.54224(18) 0.0197(5) Uani 1 1 d . . . . .
H23 H 1.092742 0.293238 0.587795 0.024 Uiso 1 1 calc R U . . .
C32 C 0.0863(3) 0.8308(3) -0.07378(19) 0.0235(6) Uani 1 1 d . . . . .
H32 H 0.059732 0.773312 -0.116917 0.028 Uiso 1 1 calc R U . . .
C11 C 1.2450(3) 0.3970(3) 0.38149(18) 0.0205(6) Uani 1 1 d . . . . .
C8 C 0.9404(3) 0.2747(3) 0.42823(19) 0.0201(6) Uani 1 1 d . . . . .
C42 C 0.4805(3) 0.6924(3) 0.21611(18) 0.0206(6) Uani 1 1 d . . . . .
C48 C 0.6231(3) 0.7656(3) 0.11115(18) 0.0195(6) Uani 1 1 d . . . . .
C31 C -0.0047(3) 0.9131(3) -0.05047(19) 0.0254(6) Uani 1 1 d . . . . .
H31 H -0.090977 0.911187 -0.078117 0.030 Uiso 1 1 calc R U . . .
C29 C 0.1625(3) 1.0008(3) 0.0561(2) 0.0247(6) Uani 1 1 d . . . . .
H29 H 0.187532 1.057202 0.100120 0.030 Uiso 1 1 calc R U . . .
C35 C 0.4224(3) 0.7041(3) 0.00847(17) 0.0188(5) Uani 1 1 d . . . . .
H35 H 0.479692 0.647247 -0.016503 0.023 Uiso 1 1 calc R U . . .
C49 C 0.5085(3) 0.8116(3) 0.04715(17) 0.0193(5) Uani 1 1 d . . . . .
H49 H 0.545442 0.849435 0.000222 0.023 Uiso 1 1 calc R U . . .
C37 C 0.3634(3) 0.6632(3) 0.16205(17) 0.0192(5) Uani 1 1 d . . . . .
C39 C 0.2417(3) 0.6840(3) 0.2787(2) 0.0249(6) Uani 1 1 d . . . . .
H39 H 0.162560 0.684163 0.298986 0.030 Uiso 1 1 calc R U . . .
C52 C 0.3768(3) 0.8176(3) -0.13439(18) 0.0257(6) Uani 1 1 d . . . . .
H52A H 0.447088 0.769056 -0.149775 0.039 Uiso 1 1 calc R U . . .
H52B H 0.409950 0.896415 -0.112053 0.039 Uiso 1 1 calc R U . . .
H52C H 0.311646 0.830819 -0.183968 0.039 Uiso 1 1 calc R U . . .
C34 C 0.3160(3) 0.7485(3) -0.06657(18) 0.0200(6) Uani 1 1 d . . . . .
C36 C 0.3586(3) 0.6273(3) 0.07083(18) 0.0194(6) Uani 1 1 d . . . . .
C5 C 1.0051(3) 0.0585(3) 0.24860(19) 0.0254(6) Uani 1 1 d . . . . .
H5 H 0.965863 0.038140 0.193370 0.030 Uiso 1 1 calc R U . . .
C10 C 1.1092(3) 0.4230(3) 0.39595(17) 0.0188(5) Uani 1 1 d . . . . .
C20 C 1.3564(3) 0.5070(3) 0.7058(2) 0.0288(7) Uani 1 1 d . . . . .
H20 H 1.357754 0.530154 0.762409 0.035 Uiso 1 1 calc R U . . .
C40 C 0.3575(3) 0.7107(3) 0.3332(2) 0.0267(6) Uani 1 1 d . . . . .
H40 H 0.356053 0.726670 0.390610 0.032 Uiso 1 1 calc R U . . .
C9 C 1.0494(3) 0.3682(3) 0.46900(17) 0.0192(6) Uani 1 1 d . . . . .
H9 H 1.005167 0.436421 0.493704 0.023 Uiso 1 1 calc R U . . .
C38 C 0.2454(3) 0.6573(3) 0.19372(19) 0.0224(6) Uani 1 1 d . . . . .
H38 H 0.168973 0.635193 0.157547 0.027 Uiso 1 1 calc R U . . .
C44 C 0.7191(3) 0.6489(3) 0.23517(19) 0.0250(6) Uani 1 1 d . . . . .
H44 H 0.710310 0.604415 0.284166 0.030 Uiso 1 1 calc R U . . .
C30 C 0.0342(3) 0.9986(3) 0.0146(2) 0.0275(7) Uani 1 1 d . . . . .
H30 H -0.026249 1.054363 0.030247 0.033 Uiso 1 1 calc R U . . .
C45 C 0.8423(3) 0.6616(3) 0.2123(2) 0.0288(6) Uani 1 1 d . . . . .
H45 H 0.914626 0.624616 0.245278 0.035 Uiso 1 1 calc R U . . .
C46 C 0.8571(3) 0.7295(3) 0.1404(2) 0.0290(7) Uani 1 1 d . . . . .
H46 H 0.939725 0.740941 0.125992 0.035 Uiso 1 1 calc R U . . .
C12 C 1.2577(3) 0.3763(3) 0.29611(19) 0.0255(6) Uani 1 1 d . . . . .
H12 H 1.183448 0.374103 0.254389 0.031 Uiso 1 1 calc R U . . .
C19 C 1.4522(3) 0.5491(3) 0.6617(2) 0.0301(7) Uani 1 1 d . . . . .
H19 H 1.519035 0.599874 0.688699 0.036 Uiso 1 1 calc R U . . .
C18 C 1.4484(3) 0.5154(3) 0.5769(2) 0.0262(6) Uani 1 1 d . . . . .
H18 H 1.511888 0.545961 0.547152 0.031 Uiso 1 1 calc R U . . .
C14 C 1.4899(3) 0.3632(3) 0.3354(2) 0.0307(7) Uani 1 1 d . . . . .
H14 H 1.572082 0.351840 0.320296 0.037 Uiso 1 1 calc R U . . .
C4 C 1.1207(3) 0.0008(3) 0.28448(19) 0.0246(6) Uani 1 1 d . . . . .
H4 H 1.158325 -0.059092 0.253846 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9479(3) 0.1460(3) 0.29452(18) 0.0216(6) Uani 1 1 d . . . . .
H6 H 0.870481 0.184075 0.269524 0.026 Uiso 1 1 calc R U . . .
C13 C 1.3790(4) 0.3591(3) 0.2733(2) 0.0311(7) Uani 1 1 d . . . . .
H13 H 1.386534 0.344935 0.216482 0.037 Uiso 1 1 calc R U . . .
C26 C 0.8741(3) 0.2142(3) 0.4966(2) 0.0250(6) Uani 1 1 d . . . . .
H26A H 0.845310 0.277569 0.531933 0.037 Uiso 1 1 calc R U . . .
H26B H 0.934943 0.160293 0.531163 0.037 Uiso 1 1 calc R U . . .
H26C H 0.800149 0.166728 0.469907 0.037 Uiso 1 1 calc R U . . .
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C2 S1 C23 104.37(13) . . ?
C28 S27 C49 104.03(13) . . ?
C8 O24 H24 109.5 . . ?
C34 O50 H50 109.5 . . ?
C3 C2 S1 115.9(2) . . ?
C3 C2 C7 120.5(3) . . ?
C7 C2 S1 123.5(2) . . ?
C33 C28 S27 125.1(2) . . ?
C29 C28 S27 115.0(2) . . ?
C29 C28 C33 119.9(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C28 C33 C34 121.6(3) . . ?
C32 C33 C28 118.4(3) . . ?
C32 C33 C34 119.8(3) . . ?
C48 C47 H47 119.5 . . ?
C46 C47 H47 119.5 . . ?
C46 C47 C48 121.0(3) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.8(3) . . ?
C48 C43 C42 122.2(3) . . ?
C44 C43 C42 119.4(3) . . ?
C44 C43 C48 118.4(3) . . ?
C22 C17 C16 123.2(3) . . ?
C18 C17 C22 118.7(3) . . ?
C18 C17 C16 118.2(3) . . ?
C17 C22 C23 123.5(3) . . ?
C21 C22 C17 119.0(3) . . ?
C21 C22 C23 117.5(3) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C40 C41 C42 121.5(3) . . ?
C15 C16 C17 118.8(3) . . ?
C11 C16 C15 117.5(3) . . ?
C11 C16 C17 123.5(3) . . ?
C2 C7 C8 120.8(2) . . ?
C6 C7 C2 118.0(3) . . ?
C6 C7 C8 121.2(2) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 C22 121.6(3) . . ?
C20 C21 H21 119.2 . . ?
S1 C23 H23 105.9 . . ?
C22 C23 S1 110.6(2) . . ?
C22 C23 H23 105.9 . . ?
C22 C23 C9 113.7(2) . . ?
C9 C23 S1 114.2(2) . . ?
C9 C23 H23 105.9 . . ?
C33 C32 H32 119.3 . . ?
C31 C32 C33 121.5(3) . . ?
C31 C32 H32 119.3 . . ?
C16 C11 C10 124.5(3) . . ?
C16 C11 C12 120.4(3) . . ?
C12 C11 C10 114.8(3) . . ?
O24 C8 C7 111.6(2) . . ?
O24 C8 C9 109.8(2) . . ?
O24 C8 C26 104.8(2) . . ?
C7 C8 C9 107.9(2) . . ?
C26 C8 C7 111.8(2) . . ?
C26 C8 C9 111.0(2) . . ?
C41 C42 C43 119.2(3) . . ?
C41 C42 C37 117.7(3) . . ?
C37 C42 C43 123.2(3) . . ?
C47 C48 C43 119.7(3) . . ?
C47 C48 C49 117.1(3) . . ?
C43 C48 C49 123.0(2) . . ?
C32 C31 H31 120.2 . . ?
C32 C31 C30 119.5(3) . . ?
C30 C31 H31 120.2 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.8 . . ?
C49 C35 H35 106.4 . . ?
C49 C35 C34 111.6(2) . . ?
C34 C35 H35 106.4 . . ?
C36 C35 H35 106.4 . . ?
C36 C35 C49 115.9(2) . . ?
C36 C35 C34 109.5(2) . . ?
S27 C49 H49 106.5 . . ?
C48 C49 S27 112.7(2) . . ?
C48 C49 C35 111.4(2) . . ?
C48 C49 H49 106.5 . . ?
C35 C49 S27 112.63(19) . . ?
C35 C49 H49 106.5 . . ?
C42 C37 C36 122.6(3) . . ?
C38 C37 C42 120.7(3) . . ?
C38 C37 C36 116.5(3) . . ?
C40 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
C38 C39 C40 119.4(3) . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C34 C52 H52A 109.5 . . ?
C34 C52 H52B 109.5 . . ?
C34 C52 H52C 109.5 . . ?
O50 C34 C33 111.3(2) . . ?
O50 C34 C35 109.2(2) . . ?
O50 C34 C52 104.6(2) . . ?
C33 C34 C35 110.8(2) . . ?
C33 C34 C52 109.4(2) . . ?
C52 C34 C35 111.4(2) . . ?
O51 C36 C35 118.6(3) . . ?
O51 C36 C37 118.5(3) . . ?
C37 C36 C35 122.9(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
O25 C10 C11 118.6(2) . . ?
O25 C10 C9 117.2(2) . . ?
C11 C10 C9 124.0(2) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 C21 119.5(3) . . ?
C19 C20 H20 120.2 . . ?
C41 C40 C39 120.3(3) . . ?
C41 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C23 C9 C8 111.9(2) . . ?
C23 C9 H9 107.0 . . ?
C8 C9 H9 107.0 . . ?
C10 C9 C23 116.7(2) . . ?
C10 C9 C8 106.8(2) . . ?
C10 C9 H9 107.0 . . ?
C37 C38 H38 119.8 . . ?
C39 C38 C37 120.4(3) . . ?
C39 C38 H38 119.8 . . ?
C43 C44 H44 119.3 . . ?
C45 C44 C43 121.4(3) . . ?
C45 C44 H44 119.3 . . ?
C31 C30 H30 119.9 . . ?
C29 C30 C31 120.2(3) . . ?
C29 C30 H30 119.9 . . ?
C44 C45 H45 120.1 . . ?
C46 C45 C44 119.8(3) . . ?
C46 C45 H45 120.1 . . ?
C47 C46 H46 120.2 . . ?
C45 C46 C47 119.5(3) . . ?
C45 C46 H46 120.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C20 C19 H19 120.1 . . ?
C20 C19 C18 119.9(3) . . ?
C18 C19 H19 120.1 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C15 C14 H14 120.1 . . ?
C15 C14 C13 119.9(3) . . ?
C13 C14 H14 120.1 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C8 C26 H26A 109.5 . . ?
C8 C26 H26B 109.5 . . ?
C8 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
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
S1 C2 1.768(3) . ?
S1 C23 1.847(3) . ?
S27 C28 1.773(3) . ?
S27 C49 1.839(3) . ?
O24 H24 0.8200 . ?
O24 C8 1.428(3) . ?
O51 C36 1.228(4) . ?
O25 C10 1.228(4) . ?
O50 H50 0.8200 . ?
O50 C34 1.430(4) . ?
C2 C3 1.399(4) . ?
C2 C7 1.403(4) . ?
C28 C33 1.409(4) . ?
C28 C29 1.397(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(4) . ?
C33 C32 1.397(4) . ?
C33 C34 1.521(4) . ?
C47 H47 0.9300 . ?
C47 C48 1.397(4) . ?
C47 C46 1.390(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.404(4) . ?
C15 C14 1.384(5) . ?
C43 C42 1.482(4) . ?
C43 C48 1.405(4) . ?
C43 C44 1.399(4) . ?
C17 C22 1.408(4) . ?
C17 C16 1.487(4) . ?
C17 C18 1.398(4) . ?
C22 C21 1.396(4) . ?
C22 C23 1.505(4) . ?
C41 H41 0.9300 . ?
C41 C42 1.400(4) . ?
C41 C40 1.384(4) . ?
C16 C11 1.399(4) . ?
C7 C8 1.524(4) . ?
C7 C6 1.397(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(5) . ?
C23 H23 0.9800 . ?
C23 C9 1.532(4) . ?
C32 H32 0.9300 . ?
C32 C31 1.387(4) . ?
C11 C10 1.490(4) . ?
C11 C12 1.401(4) . ?
C8 C9 1.571(4) . ?
C8 C26 1.523(4) . ?
C42 C37 1.403(4) . ?
C48 C49 1.514(4) . ?
C31 H31 0.9300 . ?
C31 C30 1.392(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.385(4) . ?
C35 H35 0.9800 . ?
C35 C49 1.527(4) . ?
C35 C34 1.560(4) . ?
C35 C36 1.521(4) . ?
C49 H49 0.9800 . ?
C37 C36 1.492(4) . ?
C37 C38 1.398(4) . ?
C39 H39 0.9300 . ?
C39 C40 1.389(5) . ?
C39 C38 1.385(4) . ?
C52 H52A 0.9600 . ?
C52 H52B 0.9600 . ?
C52 H52C 0.9600 . ?
C52 C34 1.527(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(4) . ?
C5 C6 1.383(4) . ?
C10 C9 1.521(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.383(5) . ?
C40 H40 0.9300 . ?
C9 H9 0.9800 . ?
C38 H38 0.9300 . ?
C44 H44 0.9300 . ?
C44 C45 1.391(4) . ?
C30 H30 0.9300 . ?
C45 H45 0.9300 . ?
C45 C46 1.385(5) . ?
C46 H46 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.377(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.388(5) . ?
C18 H18 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.387(5) . ?
C4 H4 0.9300 . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
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
S1 C2 C3 C4 -179.5(2) . . . . ?
S1 C2 C7 C8 -0.3(4) . . . . ?
S1 C2 C7 C6 178.3(2) . . . . ?
S1 C23 C9 C8 49.1(3) . . . . ?
S1 C23 C9 C10 -74.5(3) . . . . ?
S27 C28 C33 C32 179.5(2) . . . . ?
S27 C28 C33 C34 -5.1(4) . . . . ?
S27 C28 C29 C30 179.5(3) . . . . ?
O24 C8 C9 C23 166.4(2) . . . . ?
O24 C8 C9 C10 -64.7(3) . . . . ?
O25 C10 C9 C23 -170.6(3) . . . . ?
O25 C10 C9 C8 63.3(3) . . . . ?
C2 S1 C23 C22 -135.1(2) . . . . ?
C2 S1 C23 C9 -5.3(2) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C2 C7 C8 O24 166.7(2) . . . . ?
C2 C7 C8 C9 46.0(3) . . . . ?
C2 C7 C8 C26 -76.3(3) . . . . ?
C2 C7 C6 C5 1.7(4) . . . . ?
C28 S27 C49 C48 -152.3(2) . . . . ?
C28 S27 C49 C35 -25.1(2) . . . . ?
C28 C33 C32 C31 0.9(4) . . . . ?
C28 C33 C34 O50 159.7(2) . . . . ?
C28 C33 C34 C35 38.0(4) . . . . ?
C28 C33 C34 C52 -85.2(3) . . . . ?
C28 C29 C30 C31 1.1(5) . . . . ?
C3 C2 C7 C8 179.4(3) . . . . ?
C3 C2 C7 C6 -2.0(4) . . . . ?
C33 C28 C29 C30 -0.7(5) . . . . ?
C33 C32 C31 C30 -0.6(5) . . . . ?
C47 C48 C49 S27 -119.2(3) . . . . ?
C47 C48 C49 C35 113.1(3) . . . . ?
C15 C16 C11 C10 -175.4(3) . . . . ?
C15 C16 C11 C12 -0.9(4) . . . . ?
C15 C14 C13 C12 0.2(5) . . . . ?
C43 C42 C37 C36 5.7(4) . . . . ?
C43 C42 C37 C38 -179.3(3) . . . . ?
C43 C48 C49 S27 66.0(3) . . . . ?
C43 C48 C49 C35 -61.8(4) . . . . ?
C43 C44 C45 C46 1.2(5) . . . . ?
C17 C22 C21 C20 -0.5(4) . . . . ?
C17 C22 C23 S1 65.0(3) . . . . ?
C17 C22 C23 C9 -65.0(4) . . . . ?
C17 C16 C11 C10 -1.0(5) . . . . ?
C17 C16 C11 C12 173.5(3) . . . . ?
C22 C17 C16 C15 -143.7(3) . . . . ?
C22 C17 C16 C11 42.0(4) . . . . ?
C22 C17 C18 C19 1.5(4) . . . . ?
C22 C21 C20 C19 0.3(5) . . . . ?
C22 C23 C9 C8 177.2(2) . . . . ?
C22 C23 C9 C10 53.7(3) . . . . ?
C41 C42 C37 C36 -174.2(3) . . . . ?
C41 C42 C37 C38 0.8(4) . . . . ?
C16 C15 C14 C13 -0.3(5) . . . . ?
C16 C17 C22 C21 179.6(3) . . . . ?
C16 C17 C22 C23 -0.4(4) . . . . ?
C16 C17 C18 C19 -178.5(3) . . . . ?
C16 C11 C10 O25 137.9(3) . . . . ?
C16 C11 C10 C9 -47.6(4) . . . . ?
C16 C11 C12 C13 0.8(5) . . . . ?
C7 C2 C3 C4 0.8(4) . . . . ?
C7 C8 C9 C23 -71.7(3) . . . . ?
C7 C8 C9 C10 57.1(3) . . . . ?
C21 C22 C23 S1 -115.1(2) . . . . ?
C21 C22 C23 C9 115.0(3) . . . . ?
C21 C20 C19 C18 0.8(5) . . . . ?
C23 S1 C2 C3 160.2(2) . . . . ?
C23 S1 C2 C7 -20.1(3) . . . . ?
C23 C22 C21 C20 179.5(3) . . . . ?
C32 C33 C34 O50 -24.9(4) . . . . ?
C32 C33 C34 C35 -146.6(3) . . . . ?
C32 C33 C34 C52 90.2(3) . . . . ?
C32 C31 C30 C29 -0.4(5) . . . . ?
C11 C10 C9 C23 14.8(4) . . . . ?
C11 C10 C9 C8 -111.3(3) . . . . ?
C11 C12 C13 C14 -0.4(5) . . . . ?
C8 C7 C6 C5 -179.7(3) . . . . ?
C42 C43 C48 C47 174.5(3) . . . . ?
C42 C43 C48 C49 -10.8(4) . . . . ?
C42 C43 C44 C45 -176.0(3) . . . . ?
C42 C41 C40 C39 1.2(5) . . . . ?
C42 C37 C36 O51 131.2(3) . . . . ?
C42 C37 C36 C35 -51.4(4) . . . . ?
C42 C37 C38 C39 2.0(5) . . . . ?
C48 C47 C46 C45 1.0(5) . . . . ?
C48 C43 C42 C41 -134.4(3) . . . . ?
C48 C43 C42 C37 45.7(4) . . . . ?
C48 C43 C44 C45 1.6(5) . . . . ?
C29 C28 C33 C32 -0.3(4) . . . . ?
C29 C28 C33 C34 175.1(3) . . . . ?
C49 S27 C28 C33 -1.9(3) . . . . ?
C49 S27 C28 C29 177.9(2) . . . . ?
C49 C35 C34 O50 169.6(2) . . . . ?
C49 C35 C34 C33 -67.5(3) . . . . ?
C49 C35 C34 C52 54.6(3) . . . . ?
C49 C35 C36 O51 -174.4(3) . . . . ?
C49 C35 C36 C37 8.2(4) . . . . ?
C34 C33 C32 C31 -174.6(3) . . . . ?
C34 C35 C49 S27 60.3(3) . . . . ?
C34 C35 C49 C48 -171.9(2) . . . . ?
C34 C35 C36 O51 58.2(3) . . . . ?
C34 C35 C36 C37 -119.3(3) . . . . ?
C36 C35 C49 S27 -66.1(3) . . . . ?
C36 C35 C49 C48 61.7(3) . . . . ?
C36 C35 C34 O50 -60.6(3) . . . . ?
C36 C35 C34 C33 62.3(3) . . . . ?
C36 C35 C34 C52 -175.6(2) . . . . ?
C36 C37 C38 C39 177.3(3) . . . . ?
C10 C11 C12 C13 175.8(3) . . . . ?
C20 C19 C18 C17 -1.7(5) . . . . ?
C40 C41 C42 C43 177.7(3) . . . . ?
C40 C41 C42 C37 -2.4(5) . . . . ?
C40 C39 C38 C37 -3.3(5) . . . . ?
C38 C37 C36 O51 -44.1(4) . . . . ?
C38 C37 C36 C35 133.4(3) . . . . ?
C38 C39 C40 C41 1.7(5) . . . . ?
C44 C43 C42 C41 43.1(4) . . . . ?
C44 C43 C42 C37 -136.9(3) . . . . ?
C44 C43 C48 C47 -3.0(4) . . . . ?
C44 C43 C48 C49 171.7(3) . . . . ?
C44 C45 C46 C47 -2.4(5) . . . . ?
C46 C47 C48 C43 1.8(5) . . . . ?
C46 C47 C48 C49 -173.3(3) . . . . ?
C12 C11 C10 O25 -36.9(4) . . . . ?
C12 C11 C10 C9 137.7(3) . . . . ?
C18 C17 C22 C21 -0.3(4) . . . . ?
C18 C17 C22 C23 179.6(3) . . . . ?
C18 C17 C16 C15 36.2(4) . . . . ?
C18 C17 C16 C11 -138.1(3) . . . . ?
C14 C15 C16 C17 -174.0(3) . . . . ?
C14 C15 C16 C11 0.7(5) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C6 C7 C8 O24 -11.8(4) . . . . ?
C6 C7 C8 C9 -132.6(3) . . . . ?
C6 C7 C8 C26 105.1(3) . . . . ?
C6 C5 C4 C3 -1.0(5) . . . . ?
C26 C8 C9 C23 51.1(3) . . . . ?
C26 C8 C9 C10 180.0(2) . . . . ?
