#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:20:38 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298014 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/42/7134234.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_7134234
loop_
_publ_author_name
'Griggs, Samuel D.'
'Piticari, Amalia-Sofia'
'Liver, Samuel'
'Arter, Chris'
'Sievers, Sonja'
'Marsden, Stephen P.'
'Nelson, Adam'
_publ_section_title
;
 Phenotype-directed discovery of diverse, biologically-relevant molecular
 scaffolds.
;
_journal_issue                   17
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3528
_journal_page_last               3531
_journal_paper_doi               10.1039/d4cc06605g
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H23 N O5 S'
_chemical_formula_sum            'C23 H23 N O5 S'
_chemical_formula_weight         425.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-12-16 deposited with the CCDC.	2025-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                98.202(5)
_cell_angle_beta                 100.953(5)
_cell_angle_gamma                94.096(4)
_cell_formula_units_Z            2
_cell_length_a                   9.5157(5)
_cell_length_b                   9.7021(5)
_cell_length_c                   11.1463(7)
_cell_measurement_reflns_used    3820
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.4630
_cell_measurement_theta_min      4.0010
_cell_volume                     994.82(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  -7.00   1.00    3.00    --  -38.50  35.00  17.00   41
  2  ω    -87.00 -52.00   1.00    3.00    --  -38.50 -35.00-139.00   35
  3  ω     -9.00  16.00   1.00    3.00    --   40.96 -35.00-139.00   25
  4  ω     67.00 105.00   1.00    3.00    --   40.96  35.00  17.00   38
  5  ω     84.00 109.00   1.00   12.00    --  103.10 -35.00-139.00   25
  6  ω     84.00 173.00   1.00   12.00    --  103.10  35.00  17.00   89
  7  ω    -63.00 -28.00   1.00    3.00    --  -38.50  63.00 145.20   35
  8  ω    -62.00  30.00   1.00    3.00    --  -38.50  57.00  30.00   92
  9  ω    -25.00  66.00   1.00    3.00    --   40.96 -57.00-150.00   91
 10  ω    -11.00  67.00   1.00    3.00    --   40.96 -65.00  90.00   78
 11  ω     31.00  58.00   1.00    3.00    --   40.96 -65.00-178.59   27
 12  ω     17.00  58.00   1.00    3.00    --   40.96  57.00  90.00   41
 13  ω    111.00 138.00   1.00   12.00    --  103.10  30.00-150.00   27
 14  ω     83.00 108.00   1.00   12.00    --  103.10  30.00-150.00   25
 15  ω     33.00  70.00   1.00   12.00    --  103.10 -30.00  30.00   37
 16  ω     72.00 100.00   1.00   12.00    --  103.10 -64.00 -99.54   28
 17  ω     72.00 121.00   1.00   12.00    --  103.10 -65.00 137.22   49
 18  ω     35.00 129.00   1.00   12.00    --  103.10 -65.00 173.07   94
 19  ω     67.00  95.00   1.00   12.00    --  103.10 -61.00   0.00   28
 20  ω     94.00 173.00   1.00   12.00    --  103.10  45.00 -60.00   79
 21  ω     83.00 134.00   1.00   12.00    --  103.10  45.00  60.00   51
 22  ω     62.00  92.00   1.00   12.00    --  103.10 -64.00-117.99   30
 23  ω     41.00 108.00   1.00   12.00    --  103.10 -65.00  81.17   67
 24  ω     82.00 173.00   1.00   12.00    --  103.10  45.00 -90.00   91
 25  ω     93.00 121.00   1.00   12.00    --  103.10 -30.00  30.00   28
 26  ω     60.00 112.00   1.00   12.00    --  103.10 -65.00 -59.91   52
 27  ω     62.00  95.00   1.00   12.00    --  103.10 -65.00  43.42   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0770638000
_diffrn_orient_matrix_UB_12      0.1309427000
_diffrn_orient_matrix_UB_13      0.0307198000
_diffrn_orient_matrix_UB_21      0.1058643000
_diffrn_orient_matrix_UB_22      0.0874044000
_diffrn_orient_matrix_UB_23      -0.0551262000
_diffrn_orient_matrix_UB_31      -0.1016318000
_diffrn_orient_matrix_UB_32      -0.0349134000
_diffrn_orient_matrix_UB_33      -0.1278803000
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7567
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.945
_diffrn_reflns_theta_min         4.092
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.420
_exptl_crystal_description       irregular
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3645
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0408
_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)+(0.0582P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1086
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3016
_reflns_number_total             3645
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc06605g2.cif
_cod_data_source_block           sg_7_59
_cod_depositor_comments
'Adding full bibliography for 7134234--7134236.cif.'
_cod_database_code               7134234
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C23H23NO5S
_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.
;
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C)
;
_olex2_date_sample_data_collection 2023-03-08
_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.805
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.23616(5) 0.57558(5) 0.74550(5) 0.01985(14) Uani 1 1 d . . . . .
O1 O 0.31632(15) 0.01419(14) 0.50842(13) 0.0206(3) Uani 1 1 d . . . . .
O2 O 0.30213(17) 0.52693(16) 0.36316(15) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.15442(15) 0.34275(14) 0.25543(13) 0.0213(3) Uani 1 1 d . . . . .
O4 O 0.14172(16) 0.60618(15) 0.63833(14) 0.0271(3) Uani 1 1 d . . . . .
O5 O 0.18377(16) 0.55727(15) 0.85518(14) 0.0268(3) Uani 1 1 d . . . . .
N1 N 0.30182(18) 0.42865(16) 0.70392(16) 0.0190(4) Uani 1 1 d . . . . .
C1 C 0.4078(2) 0.3828(2) 0.8009(2) 0.0248(4) Uani 1 1 d . . . . .
H1A H 0.3610 0.3539 0.8667 0.030 Uiso 1 1 calc R U . . .
H1B H 0.4850 0.4591 0.8386 0.030 Uiso 1 1 calc R U . . .
C2 C 0.4683(2) 0.2597(2) 0.7353(2) 0.0249(4) Uani 1 1 d . . . . .
H2A H 0.4261 0.1704 0.7531 0.030 Uiso 1 1 calc R U . . .
H2B H 0.5741 0.2664 0.7629 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4278(2) 0.2671(2) 0.59603(19) 0.0194(4) Uani 1 1 d . . . . .
H3 H 0.5152 0.2727 0.5587 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3163(2) 0.1567(2) 0.52152(19) 0.0192(4) Uani 1 1 d . . . . .
C5 C 0.1862(2) -0.0352(2) 0.42742(18) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.1390(2) -0.1749(2) 0.38678(19) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.1940 -0.2473 0.4123 0.027 Uiso 1 1 calc R U . . .
C7 C 0.0059(2) -0.2031(2) 0.3061(2) 0.0252(5) Uani 1 1 d . . . . .
H7 H -0.0315 -0.2976 0.2752 0.030 Uiso 1 1 calc R U . . .
C8 C -0.0739(2) -0.0956(2) 0.2696(2) 0.0248(5) Uani 1 1 d . . . . .
H8 H -0.1645 -0.1191 0.2146 0.030 Uiso 1 1 calc R U . . .
C9 C -0.0250(2) 0.0446(2) 0.31114(19) 0.0208(4) Uani 1 1 d . . . . .
H9 H -0.0803 0.1168 0.2855 0.025 Uiso 1 1 calc R U . . .
C10 C 0.1090(2) 0.0755(2) 0.39223(18) 0.0190(4) Uani 1 1 d . . . . .
C11 C 0.1995(2) 0.1998(2) 0.45611(18) 0.0186(4) Uani 1 1 d . . . . .
C12 C 0.2092(2) 0.35649(19) 0.47366(18) 0.0179(4) Uani 1 1 d . . . . .
H12 H 0.1214 0.3891 0.5012 0.022 Uiso 1 1 calc R U . . .
C13 C 0.3434(2) 0.39898(19) 0.58204(18) 0.0178(4) Uani 1 1 d . . . . .
H13 H 0.4062 0.4792 0.5670 0.021 Uiso 1 1 calc R U . . .
C14 C 0.2292(2) 0.4185(2) 0.35976(19) 0.0193(4) Uani 1 1 d . . . . .
C15 C 0.1609(2) 0.4015(2) 0.14319(19) 0.0248(5) Uani 1 1 d . . . . .
H15A H 0.2619 0.4150 0.1333 0.030 Uiso 1 1 calc R U . . .
H15B H 0.1218 0.4935 0.1481 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0733(2) 0.3014(2) 0.0349(2) 0.0274(5) Uani 1 1 d . . . . .
H16A H 0.0750 0.3399 -0.0415 0.041 Uiso 1 1 calc R U . . .
H16B H -0.0262 0.2878 0.0460 0.041 Uiso 1 1 calc R U . . .
H16C H 0.1141 0.2113 0.0297 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3803(2) 0.70986(19) 0.79007(18) 0.0187(4) Uani 1 1 d . . . . .
C18 C 0.4520(2) 0.7400(2) 0.91263(19) 0.0215(4) Uani 1 1 d . . . . .
H18 H 0.4224 0.6905 0.9727 0.026 Uiso 1 1 calc R U . . .
C19 C 0.5674(2) 0.8429(2) 0.9469(2) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.6163 0.8636 1.0310 0.027 Uiso 1 1 calc R U . . .
C20 C 0.6132(2) 0.9166(2) 0.8598(2) 0.0214(4) Uani 1 1 d . . . . .
C21 C 0.5374(2) 0.8862(2) 0.7379(2) 0.0227(4) Uani 1 1 d . . . . .
H21 H 0.5658 0.9367 0.6780 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4210(2) 0.7837(2) 0.7016(2) 0.0227(4) Uani 1 1 d . . . . .
H22 H 0.3703 0.7643 0.6180 0.027 Uiso 1 1 calc R U . . .
C23 C 0.7400(2) 1.0265(2) 0.8981(2) 0.0279(5) Uani 1 1 d . . . . .
H23A H 0.7740 1.0386 0.9880 0.042 Uiso 1 1 calc R U . . .
H23B H 0.7111 1.1154 0.8744 0.042 Uiso 1 1 calc R U . . .
H23C H 0.8176 0.9971 0.8567 0.042 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -3 6 0.0208
-2 3 -6 0.0208
6 2 -3 0.0429
-6 -2 3 0.0429
3 -6 -1 0.0299
-3 6 1 0.0299
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
O4 S1 O5 120.81(9) . . ?
O4 S1 N1 107.25(9) . . ?
O4 S1 C17 108.10(9) . . ?
O5 S1 N1 105.29(9) . . ?
O5 S1 C17 106.74(9) . . ?
N1 S1 C17 108.10(9) . . ?
C4 O1 C5 103.59(15) . . ?
C14 O3 C15 115.45(15) . . ?
C1 N1 S1 115.43(13) . . ?
C1 N1 C13 110.70(16) . . ?
C13 N1 S1 120.74(13) . . ?
N1 C1 H1A 110.7 . . ?
N1 C1 H1B 110.7 . . ?
N1 C1 C2 105.18(17) . . ?
H1A C1 H1B 108.8 . . ?
C2 C1 H1A 110.7 . . ?
C2 C1 H1B 110.7 . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C1 C2 C3 106.20(17) . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C2 C3 H3 111.2 . . ?
C2 C3 C13 107.31(16) . . ?
C4 C3 C2 115.77(16) . . ?
C4 C3 H3 111.2 . . ?
C4 C3 C13 99.47(15) . . ?
C13 C3 H3 111.2 . . ?
O1 C4 C3 128.99(18) . . ?
C11 C4 O1 114.11(17) . . ?
C11 C4 C3 116.90(17) . . ?
O1 C5 C10 111.34(17) . . ?
C6 C5 O1 124.48(19) . . ?
C6 C5 C10 124.2(2) . . ?
C5 C6 H6 122.1 . . ?
C5 C6 C7 115.9(2) . . ?
C7 C6 H6 122.1 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.41(19) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.0 . . ?
C9 C8 C7 122.1(2) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 H9 121.2 . . ?
C8 C9 C10 117.5(2) . . ?
C10 C9 H9 121.2 . . ?
C5 C10 C11 104.41(18) . . ?
C9 C10 C5 118.92(18) . . ?
C9 C10 C11 136.67(19) . . ?
C4 C11 C10 106.55(17) . . ?
C4 C11 C12 110.72(17) . . ?
C10 C11 C12 142.73(19) . . ?
C11 C12 H12 109.6 . . ?
C11 C12 C13 102.24(16) . . ?
C11 C12 C14 114.22(16) . . ?
C13 C12 H12 109.6 . . ?
C14 C12 H12 109.6 . . ?
C14 C12 C13 111.40(15) . . ?
N1 C13 C3 101.93(15) . . ?
N1 C13 C12 112.08(15) . . ?
N1 C13 H13 111.4 . . ?
C3 C13 H13 111.4 . . ?
C12 C13 C3 108.20(15) . . ?
C12 C13 H13 111.4 . . ?
O2 C14 O3 123.38(19) . . ?
O2 C14 C12 123.97(19) . . ?
O3 C14 C12 112.62(16) . . ?
O3 C15 H15A 110.1 . . ?
O3 C15 H15B 110.1 . . ?
O3 C15 C16 108.22(16) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S1 119.54(15) . . ?
C18 C17 C22 120.75(18) . . ?
C22 C17 S1 119.71(16) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.51(18) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C23 120.6(2) . . ?
C21 C20 C19 118.10(19) . . ?
C21 C20 C23 121.32(19) . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.65(19) . . ?
C22 C21 H21 119.2 . . ?
C17 C22 H22 120.6 . . ?
C21 C22 C17 118.8(2) . . ?
C21 C22 H22 120.6 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 O4 1.4332(17) . ?
S1 O5 1.4337(15) . ?
S1 N1 1.6389(17) . ?
S1 C17 1.768(2) . ?
O1 C4 1.370(2) . ?
O1 C5 1.395(2) . ?
O2 C14 1.210(2) . ?
O3 C14 1.329(2) . ?
O3 C15 1.457(2) . ?
N1 C1 1.474(3) . ?
N1 C13 1.481(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.516(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.540(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.487(3) . ?
C3 C13 1.569(3) . ?
C4 C11 1.337(3) . ?
C5 C6 1.380(3) . ?
C5 C10 1.403(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.395(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.401(3) . ?
C10 C11 1.441(3) . ?
C11 C12 1.498(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.567(3) . ?
C12 C14 1.518(3) . ?
C13 H13 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.504(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.386(3) . ?
C17 C22 1.394(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.400(3) . ?
C20 C21 1.392(3) . ?
C20 C23 1.506(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.392(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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 N1 C1 C2 -171.48(13) . . . . ?
S1 N1 C13 C3 168.58(12) . . . . ?
S1 N1 C13 C12 -75.94(18) . . . . ?
S1 C17 C18 C19 178.35(16) . . . . ?
S1 C17 C22 C21 -178.16(15) . . . . ?
O1 C4 C11 C10 0.5(2) . . . . ?
O1 C4 C11 C12 -178.93(15) . . . . ?
O1 C5 C6 C7 179.94(17) . . . . ?
O1 C5 C10 C9 -179.76(16) . . . . ?
O1 C5 C10 C11 0.3(2) . . . . ?
O4 S1 N1 C1 177.15(14) . . . . ?
O4 S1 N1 C13 39.56(16) . . . . ?
O4 S1 C17 C18 153.50(16) . . . . ?
O4 S1 C17 C22 -26.88(18) . . . . ?
O5 S1 N1 C1 -53.00(16) . . . . ?
O5 S1 N1 C13 169.42(14) . . . . ?
O5 S1 C17 C18 22.13(19) . . . . ?
O5 S1 C17 C22 -158.25(16) . . . . ?
N1 S1 C17 C18 -90.71(17) . . . . ?
N1 S1 C17 C22 88.91(17) . . . . ?
N1 C1 C2 C3 16.6(2) . . . . ?
C1 N1 C13 C3 29.21(19) . . . . ?
C1 N1 C13 C12 144.69(16) . . . . ?
C1 C2 C3 C4 -109.33(19) . . . . ?
C1 C2 C3 C13 0.7(2) . . . . ?
C2 C3 C4 O1 -57.1(3) . . . . ?
C2 C3 C4 C11 123.86(19) . . . . ?
C2 C3 C13 N1 -17.36(18) . . . . ?
C2 C3 C13 C12 -135.64(16) . . . . ?
C3 C4 C11 C10 179.74(16) . . . . ?
C3 C4 C11 C12 0.3(2) . . . . ?
C4 O1 C5 C6 179.97(18) . . . . ?
C4 O1 C5 C10 0.02(19) . . . . ?
C4 C3 C13 N1 103.54(16) . . . . ?
C4 C3 C13 C12 -14.74(18) . . . . ?
C4 C11 C12 C13 -9.8(2) . . . . ?
C4 C11 C12 C14 110.64(19) . . . . ?
C5 O1 C4 C3 -179.44(18) . . . . ?
C5 O1 C4 C11 -0.4(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C10 C11 C4 -0.5(2) . . . . ?
C5 C10 C11 C12 178.7(2) . . . . ?
C6 C5 C10 C9 0.3(3) . . . . ?
C6 C5 C10 C11 -179.66(18) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C8 C9 C10 C11 179.7(2) . . . . ?
C9 C10 C11 C4 179.6(2) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C10 C5 C6 C7 -0.1(3) . . . . ?
C10 C11 C12 C13 171.0(2) . . . . ?
C10 C11 C12 C14 -68.5(3) . . . . ?
C11 C12 C13 N1 -96.26(17) . . . . ?
C11 C12 C13 C3 15.34(18) . . . . ?
C11 C12 C14 O2 -144.0(2) . . . . ?
C11 C12 C14 O3 37.9(2) . . . . ?
C13 N1 C1 C2 -29.8(2) . . . . ?
C13 C3 C4 O1 -171.62(18) . . . . ?
C13 C3 C4 C11 9.3(2) . . . . ?
C13 C12 C14 O2 -28.7(3) . . . . ?
C13 C12 C14 O3 153.08(16) . . . . ?
C14 O3 C15 C16 178.88(17) . . . . ?
C14 C12 C13 N1 141.34(16) . . . . ?
C14 C12 C13 C3 -107.06(17) . . . . ?
C15 O3 C14 O2 -2.2(3) . . . . ?
C15 O3 C14 C12 175.94(15) . . . . ?
C17 S1 N1 C1 60.80(16) . . . . ?
C17 S1 N1 C13 -76.78(16) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C17 C22 C21 1.5(3) . . . . ?
C18 C19 C20 C21 1.5(3) . . . . ?
C18 C19 C20 C23 -179.07(19) . . . . ?
C19 C20 C21 C22 -1.3(3) . . . . ?
C20 C21 C22 C17 -0.1(3) . . . . ?
C22 C17 C18 C19 -1.3(3) . . . . ?
C23 C20 C21 C22 179.26(19) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.0286 -2.9587 5.8886 -0.3629 -0.3685 -0.8559
-2.0286 2.9587 -5.8886 0.3629 0.3685 0.8559
5.5227 2.2055 -2.8777 -0.2252 0.9361 -0.2703
-5.5227 -2.2055 2.8777 0.2252 -0.9361 0.2703
2.9725 -5.5890 -1.0399 -0.9929 -0.1165 0.0260
-2.9725 5.5890 1.0399 0.9929 0.1165 -0.0260
