#------------------------------------------------------------------------------
#$Date: 2025-01-04 04:45:18 +0200 (Sat, 04 Jan 2025) $
#$Revision: 297061 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/35/1573579.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_1573579
loop_
_publ_author_name
'Jeziorna, Agata'
'Malinska, Maura'
'Sugden, Isaac'
'Paluch, Piotr'
'Dolot, Rafał'
'Dudek, Marta K.'
_publ_section_title
;
 SCXRD, CSP-NMRX and microED in the quest for three elusive polymorphs of
 meloxicam.
;
_journal_coeditor_code           ED5031
_journal_issue                   1
_journal_name_full               IUCrJ
_journal_paper_doi               10.1107/S2052252524011898
_journal_volume                  12
_journal_year                    2025
_chemical_compound_source        'Meloxicam was purchased from ABCR'
_chemical_formula_moiety         'C14 H13 N3 O4 S2'
_chemical_formula_sum            'C14 H13 N3 O4 S2'
_chemical_formula_weight         351.39
_chemical_name_common            meloxicam
_chemical_name_systematic
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide
_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             2024-04-16
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-16 deposited with the CCDC. 2024-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                65.901(2)
_cell_angle_beta                 87.2540(10)
_cell_angle_gamma                79.4390(10)
_cell_formula_units_Z            4
_cell_length_a                   11.2439(2)
_cell_length_b                   11.2772(2)
_cell_length_c                   13.4027(2)
_cell_measurement_reflns_used    21943
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4330
_cell_measurement_theta_min      3.6050
_cell_volume                     1524.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.100a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  19.00   0.50    0.51    --  -43.96  79.00 -87.00   98
  2  ω    -64.00 -38.00   0.50    0.51    --  -43.96  79.00 -87.00   52
  3  ω    -77.00 -51.00   0.50    2.03    --  -96.00  79.00 -87.00   52
  4  ω   -168.00-133.00   0.50    2.03    --  -96.00 -79.00 148.00   70
  5  ω     46.00  74.00   0.50    2.03    --  107.98 -79.00 148.00   56
  6  ω    133.00 163.00   0.50    2.03    --  107.98  79.00 -87.00   60
  7  ω    -23.00   2.00   0.50    0.51    --   12.00 101.00 135.78   50
  8  ω    -13.00  13.00   0.50    0.51    --   12.00  82.00 -38.58   52
  9  ω    -10.00  15.00   0.50    0.51    --   16.00  83.00-167.45   50
 10  ω     -2.00  23.00   0.50    0.51    --   20.00  74.00  16.44   50
 11  ω      0.00  25.00   0.50    0.51    --   20.00  71.00  54.43   50
 12  ω     15.00  40.00   0.50    0.51    --   32.00  64.00-159.01   50
 13  ω     15.00  40.00   0.50    0.51    --   32.00  64.00 -34.80   50
 14  ω     15.00  41.00   0.50    0.51    --   32.00  65.00  41.24   52
 15  ω     14.00  39.00   0.50    0.51    --   32.00  66.00-122.88   50
 16  ω     19.00  44.00   0.50    0.51    --   36.00  63.00 142.78   50
 17  ω     38.00  92.00   0.50    0.51    --   43.96-125.00 -90.00  108
 18  ω      3.00  61.00   0.50    0.51    --   43.96 -79.00 148.00  116
 19  ω    -14.00  16.00   0.50    0.51    --   43.96 -38.00-150.00   60
 20  ω     32.00  57.00   0.50    0.51    --   43.96  58.00  90.28   50
 21  ω     29.00  54.00   0.50    0.51    --   43.96  59.00 -89.32   50
 22  ω     27.00  78.00   0.50    0.51    --   43.96 -99.00   0.00  102
 23  ω     28.00  53.00   0.50    0.51    --   43.96  60.00 -80.25   50
 24  ω     28.00  53.00   0.50    0.51    --   43.96  60.00 -61.98   50
 25  ω     30.00  57.00   0.50    0.51    --   44.00  60.00-125.45   54
 26  ω     28.00  53.00   0.50    0.51    --   44.00  61.00  70.86   50
 27  ω     28.00  53.00   0.50    0.51    --   44.00  61.00  20.21   50
 28  ω     28.00  53.00   0.50    0.51    --   44.00  61.00  -5.20   50
 29  ω     28.00  53.00   0.50    0.51    --   44.00  61.00 165.68   50
 30  ω     33.00  58.00   0.50    0.51    --   48.00  59.00-154.97   50
 31  ω     33.00  58.00   0.50    0.51    --   48.00  59.00 -39.20   50
 32  ω     33.00  58.00   0.50    0.51    --   48.00  59.00 126.14   50
 33  ω    -84.00 -42.00   0.50    0.51    --  -56.00 -52.00-177.88   84
 34  ω   -129.00 -97.00   0.50    0.51    --  -56.00 -50.00 -41.37   64
 35  ω    -68.00 -42.00   0.50    0.51    --  -56.00 -51.00  63.66   52
 36  ω   -127.00 -99.00   0.50    0.51    --  -56.00 -52.00-177.88   56
 37  ω    -72.00 -41.00   0.50    0.51    --  -56.00 -50.00 -41.37   62
 38  ω   -126.00-100.00   0.50    0.51    --  -60.00 -52.00  -7.01   52
 39  ω    -73.00 -47.00   0.50    0.51    --  -60.00 -52.00  -7.01   52
 40  ω   -119.00 -94.00   0.50    0.51    --  -64.00 -48.00-111.45   50
 41  ω    -87.00 -50.00   0.50    0.51    --  -64.00 -48.00-111.45   74
 42  ω    -87.00 -54.00   0.50    0.51    --  -68.00 -52.00 -82.66   66
 43  ω    -91.00 -56.00   0.50    0.51    --  -68.00 -52.00-140.98   70
 44  ω    -81.00 -55.00   0.50    0.51    --  -68.00 -51.00  41.34   52
 45  ω    -87.00 -55.00   0.50    0.51    --  -68.00 -52.00-126.49   64
 46  ω    -84.00 -58.00   0.50    2.03    --  -72.00 -51.00   2.85   52
 47  ω   -144.00-118.00   0.50    2.03    --  -72.00 -46.00 -70.75   52
 48  ω    -85.00 -59.00   0.50    2.03    --  -72.00 -46.00 -70.75   52
 49  ω   -120.00 -94.00   0.50    2.03    --  -72.00 -51.00 165.00   52
 50  ω    -83.00 -58.00   0.50    2.03    --  -72.00 -51.00 148.84   50
 51  ω    -86.00 -58.00   0.50    2.03    --  -72.00 -50.00 -32.46   56
 52  ω    -88.00 -58.00   0.50    2.03    --  -72.00 -50.00  29.28   60
 53  ω    -84.00 -58.00   0.50    2.03    --  -72.00 -51.00 165.00   52
 54  ω    -84.00 -58.00   0.50    2.03    --  -72.00 -51.00-110.68   52
 55  ω    -89.00 -63.00   0.50    2.03    --  -76.00 -51.00 120.13   52
 56  ω    -91.00 -65.00   0.50    2.03    --  -76.00 -51.00 105.06   52
 57  ω    -87.00 -62.00   0.50    2.03    --  -76.00 -52.00  80.33   50
 58  ω    -91.00 -66.00   0.50    2.03    --  -80.00 -52.00-145.83   50
 59  ω    -92.00 -66.00   0.50    2.03    --  -80.00 -51.00 -37.09   52
 60  ω    -92.00 -67.00   0.50    2.03    --  -80.00 -52.00  93.18   50
 61  ω    -93.00 -67.00   0.50    2.03    --  -80.00 -52.00-167.99   52
 62  ω    -92.00 -66.00   0.50    2.03    --  -80.00 -50.00 137.01   52
 63  ω   -101.00 -75.00   0.50    2.03    --  -88.00 -49.00 -30.91   52
 64  ω   -101.00 -75.00   0.50    2.03    --  -88.00 -51.00  74.57   52
 65  ω   -122.00 -86.00   0.50    2.03    --  -96.00 -60.00  26.00   72
 66  ω   -154.00-127.00   0.50    2.03    --  -96.00 -60.00  26.00   54
 67  ω   -115.00 -83.00   0.50    2.03    --  -96.00 -57.00-177.76   64
 68  ω   -169.00-140.00   0.50    2.03    --  -96.00 -57.00-177.76   58
 69  ω   -113.00 -84.00   0.50    2.03    --  -96.00 -57.00 137.23   58
 70  ω   -126.00 -84.00   0.50    2.03    --  -96.00 -57.00-139.88   84
 71  ω   -168.00-136.00   0.50    2.03    --  -96.00 -57.00-139.88   64
 72  ω   -169.00 -83.00   0.50    2.03    --  -96.00 -55.00 108.87  172
 73  ω   -111.00 -85.00   0.50    2.03    --  -96.00 -56.00  78.80   52
 74  ω   -167.00-127.00   0.50    2.03    --  -96.00 -56.00  78.80   80
 75  ω   -120.00 -83.00   0.50    2.03    --  -96.00 -54.00  29.61   74
 76  ω   -111.00 -84.00   0.50    2.03    --  -96.00 -58.00 -34.49   54
 77  ω   -169.00-129.00   0.50    2.03    --  -96.00 -54.00  29.61   80
 78  ω   -150.00-117.00   0.50    2.03    --  -96.00 -58.00 -34.49   66
 79  ω   -110.00 -84.00   0.50    2.03    --  -96.00 -58.00  53.85   52
 80  ω   -121.00 -84.00   0.50    2.03    --  -96.00 -59.00 157.19   74
 81  ω   -169.00-128.00   0.50    2.03    --  -96.00 -59.00 157.19   82
 82  ω   -167.00-131.00   0.50    2.03    --  -96.00 -54.00  66.35   72
 83  ω   -113.00 -85.00   0.50    2.03    --  -96.00 -60.00 -96.68   56
 84  ω   -154.00-128.00   0.50    2.03    --  -96.00 -60.00 -96.68   52
 85  ω   -117.00 -87.00   0.50    2.03    --  -96.00 -61.00-120.00   60
 86  ω   -164.00-138.00   0.50    2.03    --  -96.00 -61.00-120.00   52
 87  ω   -170.00 -84.00   0.50    2.03    --  -96.00 -58.00 -49.27  172
 88  ω   -125.00 -86.00   0.50    2.03    --  -96.00 -54.00   6.87   78
 89  ω   -169.00-138.00   0.50    2.03    --  -96.00 -54.00   6.87   62
 90  ω   -111.00 -85.00   0.50    2.03    --  -96.00 -60.00 133.56   52
 91  ω   -151.00-125.00   0.50    2.03    --  -96.00 -60.00 133.56   52
 92  ω   -117.00 -87.00   0.50    2.03    --  -96.00 -61.00-180.00   60
 93  ω   -112.00 -83.00   0.50    2.03    --  -96.00 -55.00 -84.89   58
 94  ω    -51.00 -25.00   0.50    2.03    --  -96.00  61.00-150.00   52
 95  ω   -160.00-134.00   0.50    2.03    --  -96.00 -55.00 -84.89   52
 96  ω   -115.00 -83.00   0.50    2.03    --  -96.00 -56.00-112.68   64
 97  ω   -167.00-127.00   0.50    2.03    --  -96.00 -56.00-112.68   80
 98  ω   -110.00 -84.00   0.50    2.03    --  -96.00 -53.00-158.94   52
 99  ω   -167.00 -84.00   0.50    2.03    --  -96.00 -58.00  98.22  166
100  ω   -111.00 -86.00   0.50    2.03    --  -96.00 -54.00  66.35   50
101  ω   -115.00 -86.00   0.50    2.03    --  -96.00 -58.00 -18.96   58
102  ω   -157.00-131.00   0.50    2.03    --  -96.00 -58.00 -18.96   52
103  ω   -169.00 -84.00   0.50    2.03    --  -96.00 -59.00 -62.64  170
104  ω   -168.00-139.00   0.50    2.03    --  -96.00 -53.00-158.94   58
105  ω     65.00  99.00   0.50    2.03    --  107.98 -95.00 -30.00   68
106  ω     34.00  60.00   0.50    2.03    --  107.98 -95.00 -30.00   52
107  ω     63.00  96.00   0.50    2.03    --  107.98 -95.00   0.00   66
108  ω     73.00  99.00   0.50    2.03    --  107.98-100.00 134.23   52
109  ω     35.00  60.00   0.50    2.03    --  107.98 -95.00   0.00   50
110  ω     34.00  67.00   0.50    2.03    --  107.98-100.00 134.23   66
111  ω     35.00  94.00   0.50    2.03    --  107.98 -95.00-120.00  118
112  ω     58.00 101.00   0.50    2.03    --  107.98-125.00 150.00   86
113  ω     68.00  96.00   0.50    2.03    --  107.98 -95.00  30.00   56
114  ω     48.00  93.00   0.50    2.03    --  107.98 -95.00 -90.00   90
115  ω     35.00  86.00   0.50    2.03    --  107.98 -95.00-150.00  102
116  ω     38.00  64.00   0.50    2.03    --  107.98 -95.00  30.00   52
117  ω     34.00  95.00   0.50    2.03    --  107.98 -95.00 -60.00  122
118  ω     66.00  99.00   0.50    2.03    --  107.98 -95.00-180.00   66
119  ω     74.00  99.00   0.50    2.03    --  107.98 -95.00  60.00   50
120  ω     36.00  64.00   0.50    2.03    --  107.98 -95.00  60.00   56
121  ω     37.00  94.00   0.50    2.03    --  107.98 -95.00 150.00  114
122  ω     42.00  68.00   0.50    2.03    --  107.98 -77.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0903680000
_diffrn_orient_matrix_UB_12      -0.0460304000
_diffrn_orient_matrix_UB_13      0.0920157000
_diffrn_orient_matrix_UB_21      0.0861459000
_diffrn_orient_matrix_UB_22      -0.1334181000
_diffrn_orient_matrix_UB_23      0.0548900000
_diffrn_orient_matrix_UB_31      0.0620900000
_diffrn_orient_matrix_UB_32      0.0567692000
_diffrn_orient_matrix_UB_33      0.0662574000
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37137
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.590
_diffrn_reflns_theta_min         3.614
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.396
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.100a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_preparation       'Meloxicam was purchased from ABCR.'
_exptl_crystal_recrystallization_method
'Obtained by desolvatation of meloxicam:DMSO crystals.'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.00055(11)
_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   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         5933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0328
_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)+(0.0353P)²+1.7993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5425
_reflns_number_total             5933
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ed5031.cif
_cod_data_source_block           I
_cod_database_code               1573579
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O S'
_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   0.876
_shelx_estimated_absorpt_t_min   0.667
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C12(H12), N22(H22), C22(H22A),
 C23(H23), C24(H24), C25(H25), C32(H32)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C29(H29A,H29B,H29C), C34(H34A,H34B,H34C)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H7), O27(H27)
;
_olex2_exptl_crystal_mounting_method
'Crystal was glued to a support using the silicone grease.'
_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 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.598
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 0.60134(4) 0.78021(5) 0.46123(4) 0.01873(12) Uani 1 1 d . . . . .
S2 S 1.07681(4) 0.51838(5) 0.23955(4) 0.01876(12) Uani 1 1 d . . . . .
O1 O 0.60785(12) 0.88536(14) 0.35622(11) 0.0222(3) Uani 1 1 d . . . . .
O2 O 0.48784(12) 0.73932(15) 0.49691(13) 0.0256(3) Uani 1 1 d . . . . .
O3 O 1.01271(12) 0.62537(14) 0.37982(12) 0.0232(3) Uani 1 1 d . . . . .
O7 O 0.97946(12) 0.76693(15) 0.48841(13) 0.0254(3) Uani 1 1 d . . . . .
H7 H 1.018489 0.727393 0.452540 0.038 Uiso 1 1 calc R U . . .
N1 N 0.69971(14) 0.65217(16) 0.46254(13) 0.0182(3) Uani 1 1 d . . . . .
N2 N 0.85508(14) 0.56019(16) 0.32922(14) 0.0191(3) Uani 1 1 d . . . . .
H2 H 0.777827 0.554578 0.335436 0.023 Uiso 1 1 calc R U . . .
N19 N 0.87794(14) 0.45180(16) 0.21069(14) 0.0201(3) Uani 1 1 d . . . . .
C1 C 0.66346(17) 0.82106(19) 0.55856(16) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.59003(18) 0.8756(2) 0.62042(17) 0.0217(4) Uani 1 1 d . . . . .
H2A H 0.504648 0.882905 0.617232 0.026 Uiso 1 1 calc R U . . .
C3 C 0.64327(19) 0.9197(2) 0.68744(17) 0.0236(4) Uani 1 1 d . . . . .
H3 H 0.594170 0.958081 0.730072 0.028 Uiso 1 1 calc R U . . .
C4 C 0.76848(19) 0.9075(2) 0.69188(18) 0.0255(4) Uani 1 1 d . . . . .
H4 H 0.804420 0.938271 0.737336 0.031 Uiso 1 1 calc R U . . .
C5 C 0.84138(18) 0.8510(2) 0.63080(18) 0.0234(4) Uani 1 1 d . . . . .
H5 H 0.926801 0.842531 0.635257 0.028 Uiso 1 1 calc R U . . .
C6 C 0.79005(17) 0.80625(19) 0.56261(16) 0.0196(4) Uani 1 1 d . . . . .
C7 C 0.86504(17) 0.7458(2) 0.49771(16) 0.0199(4) Uani 1 1 d . . . . .
C8 C 0.82260(17) 0.67477(19) 0.44974(16) 0.0184(4) Uani 1 1 d . . . . .
C9 C 0.68262(19) 0.5202(2) 0.54464(18) 0.0252(4) Uani 1 1 d . . . . .
H9A H 0.701154 0.512328 0.618035 0.038 Uiso 1 1 calc R U . . .
H9B H 0.736912 0.451289 0.529559 0.038 Uiso 1 1 calc R U . . .
H9C H 0.598524 0.510072 0.540445 0.038 Uiso 1 1 calc R U . . .
C10 C 0.90220(18) 0.61950(19) 0.38458(16) 0.0197(4) Uani 1 1 d . . . . .
C11 C 0.92491(17) 0.50811(19) 0.26314(16) 0.0185(4) Uani 1 1 d . . . . .
C12 C 0.96480(17) 0.41564(19) 0.14632(16) 0.0199(4) Uani 1 1 d . . . . .
H12 H 0.946643 0.374259 0.101199 0.024 Uiso 1 1 calc R U . . .
C13 C 1.07644(17) 0.44204(19) 0.15081(16) 0.0195(4) Uani 1 1 d . . . . .
C14 C 1.18810(18) 0.4105(2) 0.09433(18) 0.0234(4) Uani 1 1 d . . . . .
H14A H 1.214430 0.492690 0.045619 0.035 Uiso 1 1 calc R U . . .
H14B H 1.170510 0.362872 0.051453 0.035 Uiso 1 1 calc R U . . .
H14C H 1.252465 0.355403 0.148958 0.035 Uiso 1 1 calc R U . . .
S21 S 0.88528(4) 0.13368(5) 0.12502(4) 0.01996(12) Uani 1 1 d . . . . .
S22 S 0.40381(4) 0.57651(5) 0.15828(4) 0.01974(12) Uani 1 1 d . . . . .
O21 O 0.87883(13) 0.23928(14) 0.01836(12) 0.0237(3) Uani 1 1 d . . . . .
O22 O 0.99849(12) 0.08179(15) 0.18482(14) 0.0286(3) Uani 1 1 d . . . . .
O23 O 0.47539(12) 0.35865(14) 0.12403(12) 0.0233(3) Uani 1 1 d . . . . .
O27 O 0.50958(12) 0.16338(14) 0.07352(12) 0.0222(3) Uani 1 1 d . . . . .
H27 H 0.469763 0.228297 0.083248 0.033 Uiso 1 1 calc R U . . .
N21 N 0.78527(14) 0.18454(16) 0.19939(14) 0.0193(3) Uani 1 1 d . . . . .
N22 N 0.62709(14) 0.41240(16) 0.19335(14) 0.0196(3) Uani 1 1 d . . . . .
H22 H 0.704624 0.395415 0.211043 0.024 Uiso 1 1 calc R U . . .
N23 N 0.59581(15) 0.58585(17) 0.25139(14) 0.0215(4) Uani 1 1 d . . . . .
C21 C 0.82669(18) 0.00596(19) 0.11314(16) 0.0197(4) Uani 1 1 d . . . . .
C22 C 0.90271(18) -0.0992(2) 0.10225(17) 0.0220(4) Uani 1 1 d . . . . .
H22A H 0.987930 -0.110000 0.110793 0.026 Uiso 1 1 calc R U . . .
C23 C 0.85213(18) -0.18871(19) 0.07860(17) 0.0216(4) Uani 1 1 d . . . . .
H23 H 0.902817 -0.259931 0.068437 0.026 Uiso 1 1 calc R U . . .
C24 C 0.72672(18) -0.1735(2) 0.06987(17) 0.0220(4) Uani 1 1 d . . . . .
H24 H 0.692454 -0.235568 0.054662 0.026 Uiso 1 1 calc R U . . .
C25 C 0.65127(18) -0.0695(2) 0.08299(16) 0.0207(4) Uani 1 1 d . . . . .
H25 H 0.565968 -0.061337 0.077509 0.025 Uiso 1 1 calc R U . . .
C26 C 0.70001(17) 0.02337(19) 0.10424(15) 0.0180(4) Uani 1 1 d . . . . .
C27 C 0.62298(17) 0.1383(2) 0.11302(16) 0.0189(4) Uani 1 1 d . . . . .
C28 C 0.66375(17) 0.21629(19) 0.15492(16) 0.0186(4) Uani 1 1 d . . . . .
C29 C 0.7967(2) 0.1082(2) 0.31981(17) 0.0273(5) Uani 1 1 d . . . . .
H29A H 0.771508 0.022967 0.339056 0.041 Uiso 1 1 calc R U . . .
H29B H 0.744983 0.157856 0.355877 0.041 Uiso 1 1 calc R U . . .
H29C H 0.881105 0.093339 0.343924 0.041 Uiso 1 1 calc R U . . .
C30 C 0.58339(17) 0.3331(2) 0.15592(16) 0.0197(4) Uani 1 1 d . . . . .
C31 C 0.55374(17) 0.5196(2) 0.20478(16) 0.0193(4) Uani 1 1 d . . . . .
C32 C 0.50555(18) 0.6878(2) 0.25077(16) 0.0207(4) Uani 1 1 d . . . . .
H32 H 0.519465 0.747093 0.281014 0.025 Uiso 1 1 calc R U . . .
C33 C 0.39688(18) 0.69948(19) 0.20545(16) 0.0202(4) Uani 1 1 d . . . . .
C34 C 0.28275(19) 0.7959(2) 0.19815(18) 0.0255(4) Uani 1 1 d . . . . .
H34A H 0.256412 0.846220 0.121321 0.038 Uiso 1 1 calc R U . . .
H34B H 0.297894 0.856572 0.229616 0.038 Uiso 1 1 calc R U . . .
H34C H 0.219400 0.747851 0.238735 0.038 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
O1 S1 N1 106.56(8) . . ?
O1 S1 C1 107.45(9) . . ?
O2 S1 O1 119.61(9) . . ?
O2 S1 N1 108.69(9) . . ?
O2 S1 C1 110.12(9) . . ?
N1 S1 C1 103.12(9) . . ?
C13 S2 C11 89.18(9) . . ?
C7 O7 H7 109.5 . . ?
C8 N1 S1 113.34(13) . . ?
C8 N1 C9 115.63(15) . . ?
C9 N1 S1 116.83(13) . . ?
C10 N2 H2 118.9 . . ?
C10 N2 C11 122.22(16) . . ?
C11 N2 H2 118.9 . . ?
C11 N19 C12 109.55(16) . . ?
C2 C1 S1 121.10(15) . . ?
C2 C1 C6 122.25(18) . . ?
C6 C1 S1 116.42(15) . . ?
C1 C2 H2A 120.5 . . ?
C1 C2 C3 118.93(19) . . ?
C3 C2 H2A 120.5 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.88(19) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.77(19) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.44(19) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 120.79(18) . . ?
C5 C6 C1 117.73(18) . . ?
C5 C6 C7 121.48(18) . . ?
O7 C7 C6 114.00(17) . . ?
O7 C7 C8 122.76(18) . . ?
C8 C7 C6 123.25(18) . . ?
N1 C8 C10 118.47(17) . . ?
C7 C8 N1 121.44(18) . . ?
C7 C8 C10 120.09(17) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N2 120.24(18) . . ?
O3 C10 C8 120.78(18) . . ?
N2 C10 C8 118.98(17) . . ?
N2 C11 S2 123.53(14) . . ?
N19 C11 S2 115.18(15) . . ?
N19 C11 N2 121.25(17) . . ?
N19 C12 H12 121.6 . . ?
C13 C12 N19 116.89(18) . . ?
C13 C12 H12 121.6 . . ?
C12 C13 S2 109.19(15) . . ?
C12 C13 C14 128.85(19) . . ?
C14 C13 S2 121.94(15) . . ?
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 . . ?
O21 S21 N21 107.00(9) . . ?
O21 S21 C21 107.47(9) . . ?
O22 S21 O21 119.44(9) . . ?
O22 S21 N21 108.48(9) . . ?
O22 S21 C21 109.96(9) . . ?
N21 S21 C21 103.26(9) . . ?
C33 S22 C31 89.12(10) . . ?
C27 O27 H27 109.5 . . ?
C28 N21 S21 112.39(13) . . ?
C28 N21 C29 114.44(16) . . ?
C29 N21 S21 116.94(14) . . ?
C30 N22 H22 118.8 . . ?
C30 N22 C31 122.42(16) . . ?
C31 N22 H22 118.8 . . ?
C31 N23 C32 109.15(17) . . ?
C22 C21 S21 120.88(15) . . ?
C22 C21 C26 122.36(18) . . ?
C26 C21 S21 116.46(15) . . ?
C21 C22 H22A 120.6 . . ?
C21 C22 C23 118.82(18) . . ?
C23 C22 H22A 120.6 . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.70(19) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.09(19) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.25(18) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C27 120.58(17) . . ?
C25 C26 C21 117.75(18) . . ?
C25 C26 C27 121.63(17) . . ?
O27 C27 C26 114.36(17) . . ?
O27 C27 C28 122.47(18) . . ?
C28 C27 C26 123.15(17) . . ?
N21 C28 C30 118.88(17) . . ?
C27 C28 N21 121.07(17) . . ?
C27 C28 C30 120.05(17) . . ?
N21 C29 H29A 109.5 . . ?
N21 C29 H29B 109.5 . . ?
N21 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O23 C30 N22 120.57(18) . . ?
O23 C30 C28 120.28(18) . . ?
N22 C30 C28 119.14(17) . . ?
N22 C31 S22 123.77(15) . . ?
N23 C31 S22 115.36(15) . . ?
N23 C31 N22 120.86(17) . . ?
N23 C32 H32 121.3 . . ?
C33 C32 N23 117.36(18) . . ?
C33 C32 H32 121.3 . . ?
C32 C33 S22 109.01(15) . . ?
C32 C33 C34 128.59(19) . . ?
C34 C33 S22 122.35(15) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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 O1 1.4322(15) . ?
S1 O2 1.4307(15) . ?
S1 N1 1.6445(17) . ?
S1 C1 1.760(2) . ?
S2 C11 1.7383(19) . ?
S2 C13 1.730(2) . ?
O3 C10 1.254(2) . ?
O7 H7 0.8400 . ?
O7 C7 1.342(2) . ?
N1 C8 1.440(2) . ?
N1 C9 1.486(3) . ?
N2 H2 0.8800 . ?
N2 C10 1.361(3) . ?
N2 C11 1.391(3) . ?
N19 C11 1.304(3) . ?
N19 C12 1.387(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.403(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(3) . ?
C6 C7 1.462(3) . ?
C7 C8 1.368(3) . ?
C8 C10 1.455(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.352(3) . ?
C13 C14 1.497(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S21 O21 1.4335(15) . ?
S21 O22 1.4306(15) . ?
S21 N21 1.6462(17) . ?
S21 C21 1.755(2) . ?
S22 C31 1.738(2) . ?
S22 C33 1.732(2) . ?
O23 C30 1.249(2) . ?
O27 H27 0.8400 . ?
O27 C27 1.340(2) . ?
N21 C28 1.440(2) . ?
N21 C29 1.486(3) . ?
N22 H22 0.8800 . ?
N22 C30 1.358(3) . ?
N22 C31 1.392(3) . ?
N23 C31 1.308(3) . ?
N23 C32 1.384(3) . ?
C21 C22 1.384(3) . ?
C21 C26 1.406(3) . ?
C22 H22A 0.9500 . ?
C22 C23 1.390(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.396(3) . ?
C26 C27 1.465(3) . ?
C27 C28 1.370(3) . ?
C28 C30 1.459(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C32 H32 0.9500 . ?
C32 C33 1.351(3) . ?
C33 C34 1.501(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O7 H7 O3 0.84 1.80 2.536(2) 145.9 . yes
O27 H27 O23 0.84 1.78 2.517(2) 146.0 . 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
_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 C8 C7 38.2(2) . . . . ?
S1 N1 C8 C10 -142.11(15) . . . . ?
S1 C1 C2 C3 -172.95(16) . . . . ?
S1 C1 C6 C5 173.39(15) . . . . ?
S1 C1 C6 C7 -6.8(3) . . . . ?
O1 S1 N1 C8 61.79(15) . . . . ?
O1 S1 N1 C9 -159.94(14) . . . . ?
O1 S1 C1 C2 99.09(18) . . . . ?
O1 S1 C1 C6 -75.44(17) . . . . ?
O2 S1 N1 C8 -168.06(13) . . . . ?
O2 S1 N1 C9 -29.79(17) . . . . ?
O2 S1 C1 C2 -32.7(2) . . . . ?
O2 S1 C1 C6 152.73(15) . . . . ?
O7 C7 C8 N1 179.11(17) . . . . ?
O7 C7 C8 C10 -0.5(3) . . . . ?
N1 S1 C1 C2 -148.58(17) . . . . ?
N1 S1 C1 C6 36.89(17) . . . . ?
N1 C8 C10 O3 -172.99(17) . . . . ?
N1 C8 C10 N2 6.5(3) . . . . ?
N19 C12 C13 S2 -0.5(2) . . . . ?
N19 C12 C13 C14 177.63(19) . . . . ?
C1 S1 N1 C8 -51.20(15) . . . . ?
C1 S1 N1 C9 87.07(15) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C6 C7 O7 164.47(18) . . . . ?
C1 C6 C7 C8 -15.0(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C1 C6 C7 178.78(19) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -179.73(19) . . . . ?
C5 C6 C7 O7 -15.7(3) . . . . ?
C5 C6 C7 C8 164.9(2) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C7 C8 N1 -1.5(3) . . . . ?
C6 C7 C8 C10 178.86(18) . . . . ?
C7 C8 C10 O3 6.7(3) . . . . ?
C7 C8 C10 N2 -173.81(18) . . . . ?
C9 N1 C8 C7 -100.6(2) . . . . ?
C9 N1 C8 C10 79.1(2) . . . . ?
C10 N2 C11 S2 -2.6(3) . . . . ?
C10 N2 C11 N19 -179.92(18) . . . . ?
C11 S2 C13 C12 -0.03(15) . . . . ?
C11 S2 C13 C14 -178.32(17) . . . . ?
C11 N2 C10 O3 -2.1(3) . . . . ?
C11 N2 C10 C8 178.35(17) . . . . ?
C11 N19 C12 C13 1.0(3) . . . . ?
C12 N19 C11 S2 -1.0(2) . . . . ?
C12 N19 C11 N2 176.55(17) . . . . ?
C13 S2 C11 N2 -176.85(17) . . . . ?
C13 S2 C11 N19 0.60(16) . . . . ?
S21 N21 C28 C27 41.4(2) . . . . ?
S21 N21 C28 C30 -139.19(16) . . . . ?
S21 C21 C22 C23 -171.56(16) . . . . ?
S21 C21 C26 C25 173.31(15) . . . . ?
S21 C21 C26 C27 -4.4(3) . . . . ?
O21 S21 N21 C28 60.41(15) . . . . ?
O21 S21 N21 C29 -164.24(14) . . . . ?
O21 S21 C21 C22 96.87(18) . . . . ?
O21 S21 C21 C26 -76.93(17) . . . . ?
O22 S21 N21 C28 -169.48(13) . . . . ?
O22 S21 N21 C29 -34.14(17) . . . . ?
O22 S21 C21 C22 -34.6(2) . . . . ?
O22 S21 C21 C26 151.57(15) . . . . ?
O27 C27 C28 N21 178.34(17) . . . . ?
O27 C27 C28 C30 -1.1(3) . . . . ?
N21 S21 C21 C22 -150.23(17) . . . . ?
N21 S21 C21 C26 35.97(17) . . . . ?
N21 C28 C30 O23 -175.65(17) . . . . ?
N21 C28 C30 N22 3.4(3) . . . . ?
N23 C32 C33 S22 -0.3(2) . . . . ?
N23 C32 C33 C34 177.07(19) . . . . ?
C21 S21 N21 C28 -52.83(15) . . . . ?
C21 S21 N21 C29 82.52(15) . . . . ?
C21 C22 C23 C24 -2.1(3) . . . . ?
C21 C26 C27 O27 162.21(17) . . . . ?
C21 C26 C27 C28 -15.9(3) . . . . ?
C22 C21 C26 C25 -0.4(3) . . . . ?
C22 C21 C26 C27 -178.14(19) . . . . ?
C22 C23 C24 C25 0.8(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C24 C25 C26 C21 -0.9(3) . . . . ?
C24 C25 C26 C27 176.84(18) . . . . ?
C25 C26 C27 O27 -15.5(3) . . . . ?
C25 C26 C27 C28 166.44(19) . . . . ?
C26 C21 C22 C23 1.9(3) . . . . ?
C26 C27 C28 N21 -3.7(3) . . . . ?
C26 C27 C28 C30 176.85(18) . . . . ?
C27 C28 C30 O23 3.8(3) . . . . ?
C27 C28 C30 N22 -177.12(18) . . . . ?
C29 N21 C28 C27 -95.2(2) . . . . ?
C29 N21 C28 C30 84.3(2) . . . . ?
C30 N22 C31 S22 -7.9(3) . . . . ?
C30 N22 C31 N23 172.98(18) . . . . ?
C31 S22 C33 C32 0.20(16) . . . . ?
C31 S22 C33 C34 -177.38(18) . . . . ?
C31 N22 C30 O23 4.2(3) . . . . ?
C31 N22 C30 C28 -174.88(17) . . . . ?
C31 N23 C32 C33 0.3(3) . . . . ?
C32 N23 C31 S22 -0.1(2) . . . . ?
C32 N23 C31 N22 179.12(17) . . . . ?
C33 S22 C31 N22 -179.25(18) . . . . ?
C33 S22 C31 N23 -0.06(16) . . . . ?
