#------------------------------------------------------------------------------
#$Date: 2024-07-05 16:41:08 +0300 (Fri, 05 Jul 2024) $
#$Revision: 292841 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/29/7132941.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_7132941
loop_
_publ_author_name
'Wei, Tao'
'Xie, Ming-Sheng'
'Guo, Hai-Ming'
_publ_section_title
;
 Construction of thioglycoside bonds via an asymmetric
 organocatalyzed sulfa-Michael/aldol reaction: access to
 4'-thionucleosides.
;
_journal_issue                   38
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5018
_journal_page_last               5021
_journal_paper_doi               10.1039/d4cc00984c
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H22 N2 O2 S'
_chemical_formula_sum            'C17 H22 N2 O2 S'
_chemical_formula_weight         318.42
_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     direct
_audit_creation_date             2021-12-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-12-30 deposited with the CCDC.	2024-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.3770(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.90480(10)
_cell_length_b                   14.2184(2)
_cell_length_c                   11.99560(10)
_cell_measurement_reflns_used    30892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2550
_cell_measurement_theta_min      4.3250
_cell_volume                     1743.51(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -16.00   1.00    1.00    --  -35.62 -34.00 165.00   89
  2  ω    -56.00  34.00   1.00    1.00    --  -35.62  34.00 -36.00   90
  3  ω     16.00 105.00   1.00    1.00    --   35.62  34.00 -36.00   89
  4  ω    -34.00  56.00   1.00    1.00    --   35.62 -34.00 165.00   90
  5  ω     87.00 177.00   1.00    1.00    --  107.12  34.00 -36.00   90
  6  ω     38.00 127.00   1.00    1.00    --  107.12 -34.00 165.00   89
  7  ω   -108.00 -34.00   1.00    1.00    --  -35.62 178.00 -30.00   74
  8  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00  30.00   73
  9  ω     57.00 108.00   1.00    1.00    --   35.62 178.00-150.00   51
 10  ω     57.00 108.00   1.00    1.00    --   35.62 178.00 150.00   51
 11  ω      9.00 103.00   1.00    1.00    --   35.62  77.00  90.00   94
 12  ω     57.00 108.00   1.00    1.00    --   35.62 178.00  30.00   51
 13  ω      6.00 107.00   1.00    1.00    --   35.62  19.00-150.00  101
 14  ω     -1.00  26.00   1.00    1.00    --   35.62  94.00 124.09   27
 15  ω      9.00 103.00   1.00    1.00    --   35.62  77.00  60.00   94
 16  ω      6.00 107.00   1.00    1.00    --   35.62  19.00 150.00  101
 17  ω     19.00 103.00   1.00    1.00    --   35.62  57.00  30.00   84
 18  ω     19.00 103.00   1.00    1.00    --   35.62  57.00 150.00   84
 19  ω     80.00 175.00   1.00    1.00    --  107.12  77.00  30.00   95
 20  ω     69.00 178.00   1.00    1.00    --  107.12  15.00-180.00  109
 21  ω     80.00 175.00   1.00    1.00    --  107.12  77.00  90.00   95
 22  ω    100.00 177.00   1.00    1.00    --  107.12 111.00-180.00   77
 23  ω     80.00 175.00   1.00    1.00    --  107.12  77.00  60.00   95
 24  ω     39.00 125.00   1.00    1.00    --  107.12 -45.00  60.00   86
 25  ω     38.00 110.00   1.00    1.00    --  107.12 -95.00-120.00   72
 26  ω     90.00 176.00   1.00    1.00    --  107.12  43.00  44.66   86
 27  ω     89.00 174.00   1.00    1.00    --  107.12  61.00  60.00   85
 28  ω     89.00 174.00   1.00    1.00    --  107.12  61.00   0.00   85
 29  ω     86.00 177.00   1.00    1.00    --  107.12  30.00  90.00   91
 30  ω     38.00 110.00   1.00    1.00    --  107.12 -95.00 -60.00   72
 31  ω     90.00 176.00   1.00    1.00    --  107.12  45.00  30.00   86
 32  ω     86.00 177.00   1.00    1.00    --  107.12  30.00 120.00   91
 33  ω     89.00 174.00   1.00    1.00    --  107.12  61.00  30.00   85
 34  ω     89.00 174.00   1.00    1.00    --  107.12  61.00  90.00   85
 35  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 -30.00   95
 36  ω     89.00 174.00   1.00    1.00    --  107.12  61.00 120.00   85
 37  ω     90.00 176.00   1.00    1.00    --  107.12  45.00  90.00   86
 38  ω     86.00 177.00   1.00    1.00    --  107.12  30.00 150.00   91
 39  ω     86.00 177.00   1.00    1.00    --  107.12  30.00  60.00   91
 40  ω     86.00 177.00   1.00    1.00    --  107.12  30.00  30.00   91
 41  ω     80.00 175.00   1.00    1.00    --  107.12  77.00   0.00   95
 42  ω     90.00 176.00   1.00    1.00    --  107.12  45.00 150.00   86
 43  ω     86.00 177.00   1.00    1.00    --  107.12  30.00   0.00   91
 44  ω     69.00 178.00   1.00    1.00    --  107.12  15.00  60.00  109
 45  ω     38.00 110.00   1.00    1.00    --  107.12 -95.00 120.00   72
 46  ω   -107.00  -6.00   1.00    1.00    --  -35.62 -19.00-150.00  101
 47  ω     19.00 103.00   1.00    1.00    --   35.62  57.00   0.00   84
 48  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00   0.00   74
 49  ω      1.00  28.00   1.00    1.00    --   35.62  92.00 -21.78   27
 50  ω      9.00 103.00   1.00    1.00    --   35.62  77.00-120.00   94
 51  ω     55.00 108.00   1.00    1.00    --   35.62-178.00 -60.00   53
 52  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 -90.00   94
 53  ω     19.00 103.00   1.00    1.00    --   35.62  57.00-180.00   84
 54  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 -60.00   94
 55  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00 -90.00   74
 56  ω     19.00 103.00   1.00    1.00    --   35.62  57.00-150.00   84
 57  ω      9.00 103.00   1.00    1.00    --   35.62  77.00   0.00   94
 58  ω     55.00 108.00   1.00    1.00    --   35.62-178.00-180.00   53
 59  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00-180.00   74
 60  ω     89.00 174.00   1.00    1.00    --  107.12  61.00-120.00   85
 61  ω     37.00 113.00   1.00    1.00    --  107.12-111.00-150.00   76
 62  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 -60.00   95
 63  ω     80.00 175.00   1.00    1.00    --  107.12  77.00-120.00   95
 64  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 150.00   95
 65  ω     80.00 175.00   1.00    1.00    --  107.12  77.00-180.00   95
 66  ω     37.00 113.00   1.00    1.00    --  107.12-111.00  30.00   76
 67  ω     80.00 175.00   1.00    1.00    --  107.12  77.00 -90.00   95
 68  ω     80.00 175.00   1.00    1.00    --  107.12  77.00-150.00   95
 69  ω     89.00 174.00   1.00    1.00    --  107.12  61.00 -90.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1474212000
_diffrn_orient_matrix_UB_12      0.0205850000
_diffrn_orient_matrix_UB_13      0.0354083000
_diffrn_orient_matrix_UB_21      -0.0238109000
_diffrn_orient_matrix_UB_22      0.0428776000
_diffrn_orient_matrix_UB_23      -0.1237542000
_diffrn_orient_matrix_UB_31      -0.0206914000
_diffrn_orient_matrix_UB_32      0.0973221000
_diffrn_orient_matrix_UB_33      0.0469016000
_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  0.0746
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            44786
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.391
_diffrn_reflns_theta_min         3.931
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6391
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0732
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1647P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2000
_refine_ls_wR_factor_ref         0.2085
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.886
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                5998
_reflns_number_total             6391
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc00984c2.cif
_cod_data_source_block           wt-20211217
_cod_depositor_comments          'Adding full bibliography for 7132941.cif.'
_cod_database_code               7132941
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'S1 N1 C1 O1'
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C8(H8), C11(H11), C10(H10), C32(H32), C33(H33), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C35(H35A,H35B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C), C44(H44A,
 H44B,H44C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O43(H43)
;
_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 6.697
_oxdiff_exptl_absorpt_empirical_full_min 0.472
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 0.43874(11) 0.27300(12) 1.11949(12) 0.0524(4) Uani 1 1 d . . . . .
O2 O 0.2256(4) 0.3636(3) 0.7431(3) 0.0523(10) Uani 1 1 d . . . . .
O1 O 0.5201(3) 0.3461(3) 0.8928(3) 0.0429(8) Uani 1 1 d . . . . .
H1 H 0.496189 0.370507 0.826751 0.064 Uiso 1 1 calc R U . . .
N2 N 0.1807(3) 0.2784(3) 0.9746(3) 0.0323(8) Uani 1 1 d . . . . .
N1 N -0.0203(4) 0.2161(3) 0.9112(4) 0.0407(9) Uani 1 1 d . . . . .
C7 C 0.0959(4) 0.2144(4) 0.9006(4) 0.0352(9) Uani 1 1 d . . . . .
C6 C -0.0117(4) 0.2841(4) 0.9976(4) 0.0373(10) Uani 1 1 d . . . . .
C5 C -0.1061(5) 0.3132(5) 1.0438(5) 0.0529(14) Uani 1 1 d . . . . .
H5 H -0.189922 0.287744 1.016926 0.064 Uiso 1 1 calc R U . . .
C4 C -0.0706(6) 0.3812(6) 1.1309(6) 0.0602(17) Uani 1 1 d . . . . .
H4 H -0.132213 0.402128 1.162854 0.072 Uiso 1 1 calc R U . . .
C3 C 0.0553(6) 0.4197(5) 1.1730(5) 0.0515(13) Uani 1 1 d . . . . .
H3 H 0.075602 0.465247 1.232262 0.062 Uiso 1 1 calc R U . . .
C2 C 0.1500(5) 0.3914(4) 1.1281(4) 0.0405(10) Uani 1 1 d . . . . .
H2 H 0.233920 0.416706 1.155886 0.049 Uiso 1 1 calc R U . . .
C1 C 0.1140(4) 0.3232(4) 1.0392(4) 0.0327(9) Uani 1 1 d . . . . .
C8 C 0.3118(4) 0.2975(4) 0.9751(4) 0.0331(10) Uani 1 1 d . . . . .
H8 H 0.327704 0.256962 0.915421 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3338(4) 0.3990(3) 0.9465(4) 0.0329(9) Uani 1 1 d . . . . .
H11 H 0.312448 0.440815 1.001995 0.039 Uiso 1 1 calc R U . . .
C10 C 0.4828(4) 0.4032(4) 0.9711(4) 0.0364(10) Uani 1 1 d . . . . .
H10 H 0.510917 0.468329 0.967906 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5465(4) 0.3628(5) 1.0963(4) 0.0448(12) Uani 1 1 d . . . . .
H9A H 0.560111 0.412343 1.155024 0.054 Uiso 1 1 calc R U . . .
H9B H 0.630782 0.335524 1.104718 0.054 Uiso 1 1 calc R U . . .
C12 C 0.2488(4) 0.4246(4) 0.8191(4) 0.0365(10) Uani 1 1 d . . . . .
C13 C 0.1909(5) 0.5221(4) 0.7941(5) 0.0459(12) Uani 1 1 d . . . . .
C15 C 0.0901(7) 0.5322(7) 0.8566(8) 0.072(2) Uani 1 1 d . . . . .
H15A H 0.027842 0.481787 0.832328 0.108 Uiso 1 1 calc R U . . .
H15B H 0.045537 0.591283 0.835225 0.108 Uiso 1 1 calc R U . . .
H15C H 0.134070 0.529746 0.941138 0.108 Uiso 1 1 calc R U . . .
C14 C 0.2970(8) 0.5965(5) 0.8426(9) 0.0708(19) Uani 1 1 d . . . . .
H14A H 0.327076 0.595944 0.927967 0.106 Uiso 1 1 calc R U . . .
H14B H 0.261858 0.657358 0.814096 0.106 Uiso 1 1 calc R U . . .
H14C H 0.368840 0.582988 0.816380 0.106 Uiso 1 1 calc R U . . .
C16 C 0.1216(9) 0.5353(7) 0.6599(7) 0.082(2) Uani 1 1 d . . . . .
H16A H 0.184966 0.533326 0.620922 0.122 Uiso 1 1 calc R U . . .
H16B H 0.077716 0.594963 0.645184 0.122 Uiso 1 1 calc R U . . .
H16C H 0.058876 0.485840 0.629646 0.122 Uiso 1 1 calc R U . . .
C17 C 0.1348(5) 0.1493(5) 0.8217(5) 0.0496(13) Uani 1 1 d . . . . .
H17A H 0.163633 0.185079 0.767613 0.074 Uiso 1 1 calc R U . . .
H17B H 0.061217 0.111212 0.777576 0.074 Uiso 1 1 calc R U . . .
H17C H 0.204683 0.109520 0.869120 0.074 Uiso 1 1 calc R U . . .
S36 S 0.53826(15) 0.54569(12) 0.32370(12) 0.0554(4) Uani 1 1 d . . . . .
O42 O 0.1672(4) 0.6121(3) 0.3879(4) 0.0491(9) Uani 1 1 d . . . . .
O43 O 0.2583(3) 0.6187(3) 0.1671(3) 0.0472(9) Uani 1 1 d . . . . .
H43 H 0.185463 0.640145 0.157241 0.071 Uiso 1 1 calc R U . . .
N23 N 0.4692(4) 0.5310(3) 0.5211(3) 0.0357(8) Uani 1 1 d . . . . .
N30 N 0.4909(4) 0.4487(4) 0.6851(3) 0.0420(10) Uani 1 1 d . . . . .
C24 C 0.5769(4) 0.5698(4) 0.6102(4) 0.0365(10) Uani 1 1 d . . . . .
C25 C 0.6652(5) 0.6398(4) 0.6113(5) 0.0486(12) Uani 1 1 d . . . . .
H25 H 0.657794 0.673915 0.543104 0.058 Uiso 1 1 calc R U . . .
C26 C 0.7655(5) 0.6571(5) 0.7185(5) 0.0523(14) Uani 1 1 d . . . . .
H26 H 0.825558 0.704669 0.723170 0.063 Uiso 1 1 calc R U . . .
C27 C 0.7769(5) 0.6036(5) 0.8198(5) 0.0525(15) Uani 1 1 d . . . . .
H27 H 0.845963 0.615767 0.890056 0.063 Uiso 1 1 calc R U . . .
C28 C 0.6902(5) 0.5342(5) 0.8187(4) 0.0479(13) Uani 1 1 d . . . . .
H28 H 0.698862 0.499378 0.886658 0.057 Uiso 1 1 calc R U . . .
C29 C 0.5878(4) 0.5172(4) 0.7115(4) 0.0384(11) Uani 1 1 d . . . . .
C31 C 0.4236(4) 0.4587(4) 0.5713(4) 0.0360(10) Uani 1 1 d . . . . .
C32 C 0.4174(5) 0.5596(4) 0.3968(4) 0.0371(10) Uani 1 1 d . . . . .
H32 H 0.343077 0.518608 0.355893 0.044 Uiso 1 1 calc R U . . .
C33 C 0.3699(4) 0.6608(4) 0.3753(4) 0.0363(10) Uani 1 1 d . . . . .
H33 H 0.438574 0.702353 0.425726 0.044 Uiso 1 1 calc R U . . .
C34 C 0.3540(5) 0.6780(4) 0.2434(4) 0.0405(11) Uani 1 1 d . . . . .
H34 H 0.333513 0.744084 0.221820 0.049 Uiso 1 1 calc R U . . .
C35 C 0.4861(5) 0.6515(5) 0.2356(5) 0.0527(14) Uani 1 1 d . . . . .
H35A H 0.548931 0.701705 0.266909 0.063 Uiso 1 1 calc R U . . .
H35B H 0.478061 0.639909 0.153657 0.063 Uiso 1 1 calc R U . . .
C37 C 0.2451(4) 0.6763(4) 0.4034(4) 0.0350(9) Uani 1 1 d . . . . .
C38 C 0.2243(5) 0.7704(4) 0.4554(5) 0.0425(11) Uani 1 1 d . . . . .
C39 C 0.2415(8) 0.8511(5) 0.3799(8) 0.0695(19) Uani 1 1 d . . . . .
H39A H 0.329676 0.851317 0.380121 0.104 Uiso 1 1 calc R U . . .
H39B H 0.224108 0.909466 0.411785 0.104 Uiso 1 1 calc R U . . .
H39C H 0.181812 0.843765 0.299830 0.104 Uiso 1 1 calc R U . . .
C40 C 0.3279(9) 0.7768(7) 0.5817(6) 0.081(2) Uani 1 1 d . . . . .
H40A H 0.319359 0.723674 0.627745 0.122 Uiso 1 1 calc R U . . .
H40B H 0.314908 0.833721 0.619226 0.122 Uiso 1 1 calc R U . . .
H40C H 0.413747 0.777147 0.576430 0.122 Uiso 1 1 calc R U . . .
C41 C 0.0884(7) 0.7743(6) 0.4639(7) 0.0677(18) Uani 1 1 d . . . . .
H41A H 0.023767 0.774487 0.385398 0.102 Uiso 1 1 calc R U . . .
H41B H 0.080070 0.830576 0.504990 0.102 Uiso 1 1 calc R U . . .
H41C H 0.075557 0.720400 0.506774 0.102 Uiso 1 1 calc R U . . .
C44 C 0.3122(6) 0.3967(5) 0.5023(5) 0.0503(13) Uani 1 1 d . . . . .
H44A H 0.235607 0.434368 0.466003 0.075 Uiso 1 1 calc R U . . .
H44B H 0.295309 0.351778 0.554953 0.075 Uiso 1 1 calc R U . . .
H44C H 0.334344 0.364176 0.441784 0.075 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'
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'
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
C9 S1 C8 92.2(2) . . ?
C10 O1 H1 109.5 . . ?
C7 N2 C1 107.3(3) . . ?
C7 N2 C8 124.3(4) . . ?
C1 N2 C8 128.2(4) . . ?
C7 N1 C6 105.5(4) . . ?
N2 C7 C17 123.0(4) . . ?
N1 C7 N2 112.2(4) . . ?
N1 C7 C17 124.8(5) . . ?
N1 C6 C1 110.1(4) . . ?
C5 C6 N1 129.4(5) . . ?
C5 C6 C1 120.6(5) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 C6 117.4(5) . . ?
C4 C5 H5 121.3 . . ?
C5 C4 H4 119.0 . . ?
C5 C4 C3 122.0(5) . . ?
C3 C4 H4 119.0 . . ?
C4 C3 H3 119.4 . . ?
C2 C3 C4 121.3(6) . . ?
C2 C3 H3 119.4 . . ?
C3 C2 H2 121.6 . . ?
C3 C2 C1 116.8(5) . . ?
C1 C2 H2 121.6 . . ?
N2 C1 C6 104.9(4) . . ?
N2 C1 C2 133.1(4) . . ?
C2 C1 C6 121.9(4) . . ?
S1 C8 H8 108.1 . . ?
N2 C8 S1 112.7(3) . . ?
N2 C8 H8 108.1 . . ?
N2 C8 C11 114.1(4) . . ?
C11 C8 S1 105.5(3) . . ?
C11 C8 H8 108.1 . . ?
C8 C11 H11 109.2 . . ?
C8 C11 C10 103.4(4) . . ?
C8 C11 C12 111.3(4) . . ?
C10 C11 H11 109.2 . . ?
C12 C11 H11 109.2 . . ?
C12 C11 C10 114.4(3) . . ?
O1 C10 C11 112.3(4) . . ?
O1 C10 H10 110.6 . . ?
O1 C10 C9 107.5(4) . . ?
C11 C10 H10 110.6 . . ?
C9 C10 C11 105.1(4) . . ?
C9 C10 H10 110.6 . . ?
S1 C9 H9A 110.0 . . ?
S1 C9 H9B 110.0 . . ?
C10 C9 S1 108.4(3) . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
O2 C12 C11 118.2(5) . . ?
O2 C12 C13 122.7(4) . . ?
C13 C12 C11 118.9(4) . . ?
C12 C13 C15 108.0(5) . . ?
C12 C13 C14 110.6(5) . . ?
C12 C13 C16 109.9(6) . . ?
C14 C13 C15 109.0(6) . . ?
C14 C13 C16 110.3(6) . . ?
C16 C13 C15 109.0(6) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C35 S36 C32 93.3(2) . . ?
C34 O43 H43 109.5 . . ?
C24 N23 C32 126.6(4) . . ?
C31 N23 C24 107.3(4) . . ?
C31 N23 C32 126.1(4) . . ?
C31 N30 C29 105.5(4) . . ?
C25 C24 N23 133.5(5) . . ?
C25 C24 C29 122.1(5) . . ?
C29 C24 N23 104.4(4) . . ?
C24 C25 H25 121.4 . . ?
C24 C25 C26 117.2(6) . . ?
C26 C25 H25 121.4 . . ?
C25 C26 H26 119.7 . . ?
C25 C26 C27 120.7(6) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 118.9 . . ?
C28 C27 C26 122.1(5) . . ?
C28 C27 H27 118.9 . . ?
C27 C28 H28 121.2 . . ?
C27 C28 C29 117.6(5) . . ?
C29 C28 H28 121.2 . . ?
N30 C29 C24 110.5(4) . . ?
N30 C29 C28 129.1(5) . . ?
C24 C29 C28 120.3(5) . . ?
N23 C31 C44 123.2(4) . . ?
N30 C31 N23 112.4(4) . . ?
N30 C31 C44 124.3(5) . . ?
S36 C32 H32 107.7 . . ?
N23 C32 S36 111.9(3) . . ?
N23 C32 H32 107.7 . . ?
N23 C32 C33 115.1(4) . . ?
C33 C32 S36 106.3(3) . . ?
C33 C32 H32 107.7 . . ?
C32 C33 H33 108.9 . . ?
C32 C33 C34 103.4(4) . . ?
C32 C33 C37 112.1(4) . . ?
C34 C33 H33 108.9 . . ?
C37 C33 H33 108.9 . . ?
C37 C33 C34 114.2(4) . . ?
O43 C34 C33 111.4(4) . . ?
O43 C34 H34 110.8 . . ?
O43 C34 C35 108.4(5) . . ?
C33 C34 H34 110.8 . . ?
C35 C34 C33 104.5(4) . . ?
C35 C34 H34 110.8 . . ?
S36 C35 H35A 110.5 . . ?
S36 C35 H35B 110.5 . . ?
C34 C35 S36 106.3(4) . . ?
C34 C35 H35A 110.5 . . ?
C34 C35 H35B 110.5 . . ?
H35A C35 H35B 108.7 . . ?
O42 C37 C33 119.1(5) . . ?
O42 C37 C38 121.6(5) . . ?
C38 C37 C33 119.2(4) . . ?
C37 C38 C40 106.9(5) . . ?
C39 C38 C37 110.7(4) . . ?
C39 C38 C40 109.9(6) . . ?
C39 C38 C41 109.8(6) . . ?
C41 C38 C37 110.3(5) . . ?
C41 C38 C40 109.2(6) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C38 C41 H41A 109.5 . . ?
C38 C41 H41B 109.5 . . ?
C38 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C31 C44 H44A 109.5 . . ?
C31 C44 H44B 109.5 . . ?
C31 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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 C8 1.835(4) . ?
S1 C9 1.821(6) . ?
O2 C12 1.221(7) . ?
O1 H1 0.8200 . ?
O1 C10 1.405(6) . ?
N2 C7 1.378(6) . ?
N2 C1 1.388(6) . ?
N2 C8 1.454(5) . ?
N1 C7 1.318(6) . ?
N1 C6 1.396(7) . ?
C7 C17 1.487(7) . ?
C6 C5 1.392(7) . ?
C6 C1 1.401(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.376(10) . ?
C4 H4 0.9300 . ?
C4 C3 1.400(9) . ?
C3 H3 0.9300 . ?
C3 C2 1.380(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.393(7) . ?
C8 H8 0.9800 . ?
C8 C11 1.521(7) . ?
C11 H11 0.9800 . ?
C11 C10 1.547(5) . ?
C11 C12 1.530(6) . ?
C10 H10 0.9800 . ?
C10 C9 1.531(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C12 C13 1.509(8) . ?
C13 C15 1.537(8) . ?
C13 C14 1.526(9) . ?
C13 C16 1.533(8) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
S36 C32 1.830(5) . ?
S36 C35 1.812(7) . ?
O42 C37 1.217(6) . ?
O43 H43 0.8200 . ?
O43 C34 1.404(7) . ?
N23 C24 1.398(6) . ?
N23 C31 1.371(6) . ?
N23 C32 1.456(5) . ?
N30 C29 1.389(7) . ?
N30 C31 1.313(6) . ?
C24 C25 1.381(8) . ?
C24 C29 1.397(7) . ?
C25 H25 0.9300 . ?
C25 C26 1.390(8) . ?
C26 H26 0.9300 . ?
C26 C27 1.402(10) . ?
C27 H27 0.9300 . ?
C27 C28 1.364(10) . ?
C28 H28 0.9300 . ?
C28 C29 1.399(7) . ?
C31 C44 1.495(7) . ?
C32 H32 0.9800 . ?
C32 C33 1.520(7) . ?
C33 H33 0.9800 . ?
C33 C34 1.551(6) . ?
C33 C37 1.528(6) . ?
C34 H34 0.9800 . ?
C34 C35 1.523(7) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C37 C38 1.526(7) . ?
C38 C39 1.514(8) . ?
C38 C40 1.545(8) . ?
C38 C41 1.522(8) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 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 C8 C11 C10 47.7(4) . . . . ?
S1 C8 C11 C12 170.9(3) . . . . ?
O2 C12 C13 C15 109.4(6) . . . . ?
O2 C12 C13 C14 -131.4(6) . . . . ?
O2 C12 C13 C16 -9.4(7) . . . . ?
O1 C10 C9 S1 -87.1(4) . . . . ?
N2 C8 C11 C10 171.9(3) . . . . ?
N2 C8 C11 C12 -64.9(5) . . . . ?
N1 C6 C5 C4 178.8(6) . . . . ?
N1 C6 C1 N2 0.9(5) . . . . ?
N1 C6 C1 C2 -178.5(5) . . . . ?
C7 N2 C1 C6 -1.2(5) . . . . ?
C7 N2 C1 C2 178.1(5) . . . . ?
C7 N2 C8 S1 -120.1(4) . . . . ?
C7 N2 C8 C11 119.7(5) . . . . ?
C7 N1 C6 C5 -179.1(6) . . . . ?
C7 N1 C6 C1 -0.2(6) . . . . ?
C6 N1 C7 N2 -0.6(6) . . . . ?
C6 N1 C7 C17 177.3(5) . . . . ?
C6 C5 C4 C3 -0.5(11) . . . . ?
C5 C6 C1 N2 179.9(5) . . . . ?
C5 C6 C1 C2 0.5(8) . . . . ?
C5 C4 C3 C2 0.4(11) . . . . ?
C4 C3 C2 C1 0.2(9) . . . . ?
C3 C2 C1 N2 -179.8(5) . . . . ?
C3 C2 C1 C6 -0.6(8) . . . . ?
C1 N2 C7 N1 1.2(5) . . . . ?
C1 N2 C7 C17 -176.8(5) . . . . ?
C1 N2 C8 S1 64.9(6) . . . . ?
C1 N2 C8 C11 -55.4(6) . . . . ?
C1 C6 C5 C4 0.0(9) . . . . ?
C8 S1 C9 C10 -4.5(4) . . . . ?
C8 N2 C7 N1 -174.7(4) . . . . ?
C8 N2 C7 C17 7.3(7) . . . . ?
C8 N2 C1 C6 174.5(4) . . . . ?
C8 N2 C1 C2 -6.2(9) . . . . ?
C8 C11 C10 O1 65.0(5) . . . . ?
C8 C11 C10 C9 -51.5(5) . . . . ?
C8 C11 C12 O2 -33.4(5) . . . . ?
C8 C11 C12 C13 143.1(4) . . . . ?
C11 C10 C9 S1 32.7(5) . . . . ?
C11 C12 C13 C15 -66.9(6) . . . . ?
C11 C12 C13 C14 52.3(6) . . . . ?
C11 C12 C13 C16 174.3(5) . . . . ?
C10 C11 C12 O2 83.3(6) . . . . ?
C10 C11 C12 C13 -100.2(5) . . . . ?
C9 S1 C8 N2 -150.5(4) . . . . ?
C9 S1 C8 C11 -25.4(3) . . . . ?
C12 C11 C10 O1 -56.1(6) . . . . ?
C12 C11 C10 C9 -172.7(4) . . . . ?
S36 C32 C33 C34 42.0(4) . . . . ?
S36 C32 C33 C37 165.5(3) . . . . ?
O42 C37 C38 C39 -130.6(6) . . . . ?
O42 C37 C38 C40 109.8(6) . . . . ?
O42 C37 C38 C41 -8.8(7) . . . . ?
O43 C34 C35 S36 -77.6(5) . . . . ?
N23 C24 C25 C26 -177.3(5) . . . . ?
N23 C24 C29 N30 0.3(5) . . . . ?
N23 C24 C29 C28 177.3(4) . . . . ?
N23 C32 C33 C34 166.5(4) . . . . ?
N23 C32 C33 C37 -69.9(5) . . . . ?
C24 N23 C31 N30 1.1(6) . . . . ?
C24 N23 C31 C44 -177.0(5) . . . . ?
C24 N23 C32 S36 60.5(6) . . . . ?
C24 N23 C32 C33 -61.1(6) . . . . ?
C24 C25 C26 C27 1.5(8) . . . . ?
C25 C24 C29 N30 -177.1(5) . . . . ?
C25 C24 C29 C28 -0.1(8) . . . . ?
C25 C26 C27 C28 -1.2(9) . . . . ?
C26 C27 C28 C29 0.3(8) . . . . ?
C27 C28 C29 N30 176.8(5) . . . . ?
C27 C28 C29 C24 0.4(8) . . . . ?
C29 N30 C31 N23 -0.9(6) . . . . ?
C29 N30 C31 C44 177.2(5) . . . . ?
C29 C24 C25 C26 -0.9(8) . . . . ?
C31 N23 C24 C25 176.1(6) . . . . ?
C31 N23 C24 C29 -0.8(5) . . . . ?
C31 N23 C32 S36 -117.1(5) . . . . ?
C31 N23 C32 C33 121.3(5) . . . . ?
C31 N30 C29 C24 0.4(5) . . . . ?
C31 N30 C29 C28 -176.3(5) . . . . ?
C32 S36 C35 C34 -14.8(4) . . . . ?
C32 N23 C24 C25 -1.9(9) . . . . ?
C32 N23 C24 C29 -178.8(4) . . . . ?
C32 N23 C31 N30 179.1(5) . . . . ?
C32 N23 C31 C44 0.9(8) . . . . ?
C32 C33 C34 O43 63.1(5) . . . . ?
C32 C33 C34 C35 -53.8(5) . . . . ?
C32 C33 C37 O42 -31.7(6) . . . . ?
C32 C33 C37 C38 145.6(4) . . . . ?
C33 C34 C35 S36 41.3(5) . . . . ?
C33 C37 C38 C39 52.2(6) . . . . ?
C33 C37 C38 C40 -67.4(6) . . . . ?
C33 C37 C38 C41 174.0(5) . . . . ?
C34 C33 C37 O42 85.6(6) . . . . ?
C34 C33 C37 C38 -97.2(5) . . . . ?
C35 S36 C32 N23 -142.8(4) . . . . ?
C35 S36 C32 C33 -16.3(4) . . . . ?
C37 C33 C34 O43 -59.1(6) . . . . ?
C37 C33 C34 C35 -176.0(5) . . . . ?
