# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TB-IH_330
_database_code_depnum_ccdc_archive 'CCDC 1469769'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(Butylcarbamoyl)-4-methylbenzenesulfonamide
_chemical_name_common            'Tolbutamide form IH'
_chemical_formula_moiety         'C12 H18 N2 O3 S'
_chemical_formula_sum            'C12 H18 N2 O3 S'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_melting_point          401

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      330(2)
_chemical_formula_weight         270.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P n a 21'
_symmetry_int_tables_number      33
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   20.7500(15)
_cell_length_b                   7.9160(7)
_cell_length_c                   9.0580(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1487.84(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    330(1)
_cell_measurement_reflns_used    1597
_cell_measurement_theta_min      1.9589
_cell_measurement_theta_max      29.1356

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90326
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            5834
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.963
_diffrn_reflns_theta_max         26.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_point_group_measured_fraction_full 0.926
_reflns_number_total             2781
_reflns_number_gt                1609
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     0.825
_reflns_Friedel_fraction_full    0.842

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997) 
;
_computing_publication_material  
;
 SHELXL-2014/6 (Sheldrick, 2014), WinGX (Farrugia, 
 1999), Mercury (Macrae et al., 2008)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0922P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 510 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2781
_refine_ls_number_parameters     174
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.10963(7) -0.1067(2) 0.12810(15) 0.0877(6) Uani 1 1 d . . . . .
O1 O 0.1403(2) -0.1869(7) 0.0056(5) 0.1059(15) Uani 1 1 d . . . . .
O2 O 0.1034(2) -0.2011(7) 0.2615(5) 0.0963(15) Uani 1 1 d . . . . .
O3 O 0.0011(2) 0.0577(6) 0.2764(4) 0.0981(14) Uani 1 1 d . . . . .
N1 N 0.0394(2) -0.0545(7) 0.0633(5) 0.0890(17) Uani 1 1 d . . . . .
H1 H 0.0290 -0.0881 -0.0238 0.107 Uiso 1 1 calc R U . . .
N2 N -0.0512(3) 0.1067(7) 0.0628(5) 0.0907(16) Uani 1 1 d . . . . .
H2 H -0.0528 0.0826 -0.0297 0.109 Uiso 1 1 calc R U . . .
C1 C 0.2475(5) 0.5462(13) 0.2651(17) 0.158(4) Uani 1 1 d . . . . .
H1A H 0.2464 0.5650 0.3698 0.237 Uiso 1 1 calc R U . . .
H1B H 0.2259 0.6373 0.2156 0.237 Uiso 1 1 calc R U . . .
H1C H 0.2915 0.5409 0.2325 0.237 Uiso 1 1 calc R U . . .
C2 C 0.2144(4) 0.3835(11) 0.2299(11) 0.110(2) Uani 1 1 d . . . . .
C3 C 0.2212(4) 0.2395(14) 0.3138(11) 0.129(3) Uani 1 1 d . . . . .
H3 H 0.2487 0.2421 0.3948 0.155 Uiso 1 1 calc R U . . .
C4 C 0.1898(4) 0.0965(12) 0.2839(9) 0.114(3) Uani 1 1 d . . . . .
H4 H 0.1963 0.0029 0.3441 0.137 Uiso 1 1 calc R U . . .
C5 C 0.1483(3) 0.0837(9) 0.1670(7) 0.0874(19) Uani 1 1 d . . . . .
C6 C 0.1404(4) 0.2231(11) 0.0795(8) 0.114(3) Uani 1 1 d . . . . .
H6 H 0.1125 0.2185 -0.0008 0.137 Uiso 1 1 calc R U . . .
C7 C 0.1730(5) 0.3688(12) 0.1090(12) 0.128(3) Uani 1 1 d . . . . .
H7 H 0.1676 0.4611 0.0468 0.153 Uiso 1 1 calc R U . . .
C8 C -0.0049(3) 0.0422(8) 0.1424(6) 0.0788(16) Uani 1 1 d . . . . .
C9 C -0.1006(4) 0.2185(12) 0.1248(11) 0.133(3) Uani 1 1 d D U . . .
H9A H -0.1081 0.1910 0.2277 0.160 Uiso 1 1 calc R U . . .
H9B H -0.1408 0.2052 0.0714 0.160 Uiso 1 1 calc R U . . .
C10 C -0.0758(11) 0.4033(17) 0.110(3) 0.292(9) Uani 1 1 d D U . . .
H10A H -0.0355 0.4174 0.1634 0.351 Uiso 0.59(3) 1 calc R U P A 1
H10B H -0.0689 0.4323 0.0075 0.351 Uiso 0.59(3) 1 calc R U P A 1
H10C H -0.0351 0.4011 0.0577 0.351 Uiso 0.41(3) 1 calc R U P A 2
H10D H -0.1062 0.4659 0.0502 0.351 Uiso 0.41(3) 1 calc R U P A 2
C11A C -0.1279(15) 0.513(3) 0.177(6) 0.283(13) Uani 0.59(3) 1 d D U P A 1
H11A H -0.1652 0.5261 0.1131 0.340 Uiso 0.59(3) 1 calc R U P A 1
H11B H -0.1410 0.4767 0.2746 0.340 Uiso 0.59(3) 1 calc R U P A 1
C11B C -0.066(3) 0.497(4) 0.250(5) 0.315(14) Uani 0.41(3) 1 d D U P A 2
H11C H -0.0219 0.4955 0.2847 0.378 Uiso 0.41(3) 1 calc R U P A 2
H11D H -0.0952 0.4616 0.3285 0.378 Uiso 0.41(3) 1 calc R U P A 2
C12 C -0.0855(14) 0.664(2) 0.179(3) 0.331(11) Uani 1 1 d D U . . .
H12A H -0.1087 0.7580 0.2190 0.497 Uiso 0.59(3) 1 calc R U P A 1
H12B H -0.0484 0.6411 0.2387 0.497 Uiso 0.59(3) 1 calc R U P A 1
H12C H -0.0721 0.6896 0.0799 0.497 Uiso 0.59(3) 1 calc R U P A 1
H12D H -0.0834 0.7526 0.2507 0.497 Uiso 0.41(3) 1 calc R U P A 2
H12E H -0.0567 0.6884 0.0988 0.497 Uiso 0.41(3) 1 calc R U P A 2
H12F H -0.1288 0.6550 0.1418 0.497 Uiso 0.41(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O2 1.427(5) . ?
S1 O1 1.427(5) . ?
S1 N1 1.625(6) . ?
S1 C5 1.744(8) . ?
O3 C8 1.226(7) . ?
N1 C8 1.394(8) . ?
N1 H1 0.8600 . ?
N2 C8 1.306(7) . ?
N2 C9 1.466(9) . ?
N2 H2 0.8600 . ?
C1 C2 1.494(12) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.377(12) . ?
C2 C7 1.396(13) . ?
C3 C4 1.333(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(9) . ?
C6 C7 1.364(12) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C9 C10 1.556(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11B 1.48(3) . ?
C10 C11A 1.51(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C11A C12 1.48(2) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C11B C12 1.53(3) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H12D 0.9600 . ?
C12 H12E 0.9600 . ?
C12 H12F 0.9600 . ?

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
O2 S1 O1 117.8(3) . . ?
O2 S1 N1 110.9(3) . . ?
O1 S1 N1 103.4(3) . . ?
O2 S1 C5 108.9(3) . . ?
O1 S1 C5 109.7(3) . . ?
N1 S1 C5 105.4(3) . . ?
C8 N1 S1 123.0(4) . . ?
C8 N1 H1 118.5 . . ?
S1 N1 H1 118.5 . . ?
C8 N2 C9 122.7(6) . . ?
C8 N2 H2 118.7 . . ?
C9 N2 H2 118.7 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 115.3(8) . . ?
C3 C2 C1 123.3(9) . . ?
C7 C2 C1 121.5(9) . . ?
C4 C3 C2 122.7(8) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 121.8(8) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 117.6(7) . . ?
C4 C5 S1 120.7(6) . . ?
C6 C5 S1 121.6(5) . . ?
C7 C6 C5 120.6(7) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 122.0(9) . . ?
C6 C7 H7 119.0 . . ?
C2 C7 H7 119.0 . . ?
O3 C8 N2 125.5(6) . . ?
O3 C8 N1 119.9(5) . . ?
N2 C8 N1 114.6(5) . . ?
N2 C9 C10 107.7(9) . . ?
N2 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
N2 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C11B C10 C9 116(2) . . ?
C11A C10 C9 105.6(16) . . ?
C11A C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
C11A C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
C11B C10 H10C 108.2 . . ?
C9 C10 H10C 108.2 . . ?
C11B C10 H10D 108.2 . . ?
C9 C10 H10D 108.2 . . ?
H10C C10 H10D 107.4 . . ?
C12 C11A C10 92.4(17) . . ?
C12 C11A H11A 113.2 . . ?
C10 C11A H11A 113.2 . . ?
C12 C11A H11B 113.2 . . ?
C10 C11A H11B 113.2 . . ?
H11A C11A H11B 110.6 . . ?
C10 C11B C12 91.9(19) . . ?
C10 C11B H11C 113.3 . . ?
C12 C11B H11C 113.3 . . ?
C10 C11B H11D 113.3 . . ?
C12 C11B H11D 113.3 . . ?
H11C C11B H11D 110.6 . . ?
C11A C12 H12A 109.5 . . ?
C11A C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11A C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11B C12 H12D 109.5 . . ?
C11B C12 H12E 109.5 . . ?
H12D C12 H12E 109.5 . . ?
C11B C12 H12F 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?

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
O2 S1 N1 C8 59.1(6) . . . . ?
O1 S1 N1 C8 -173.8(5) . . . . ?
C5 S1 N1 C8 -58.7(6) . . . . ?
C7 C2 C3 C4 -1.0(15) . . . . ?
C1 C2 C3 C4 177.9(10) . . . . ?
C2 C3 C4 C5 -0.3(16) . . . . ?
C3 C4 C5 C6 0.8(13) . . . . ?
C3 C4 C5 S1 178.4(8) . . . . ?
O2 S1 C5 C4 27.2(7) . . . . ?
O1 S1 C5 C4 -103.0(6) . . . . ?
N1 S1 C5 C4 146.2(6) . . . . ?
O2 S1 C5 C6 -155.3(6) . . . . ?
O1 S1 C5 C6 74.5(7) . . . . ?
N1 S1 C5 C6 -36.2(6) . . . . ?
C4 C5 C6 C7 0.0(12) . . . . ?
S1 C5 C6 C7 -177.6(7) . . . . ?
C5 C6 C7 C2 -1.3(14) . . . . ?
C3 C2 C7 C6 1.8(14) . . . . ?
C1 C2 C7 C6 -177.1(10) . . . . ?
C9 N2 C8 O3 4.5(11) . . . . ?
C9 N2 C8 N1 -177.0(7) . . . . ?
S1 N1 C8 O3 -17.5(9) . . . . ?
S1 N1 C8 N2 164.0(5) . . . . ?
C8 N2 C9 C10 90.4(15) . . . . ?
N2 C9 C10 C11B -118(3) . . . . ?
N2 C9 C10 C11A -179(2) . . . . ?
C9 C10 C11A C12 168(3) . . . . ?
C9 C10 C11B C12 -146(2) . . . . ?

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
N1 H1 O3 0.86 1.93 2.731(6) 154.5 2_554
N2 H2 O2 0.86 2.36 3.030(7) 135.3 2_554
N2 H2 O3 0.86 2.34 3.084(7) 145.0 2_554

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6


_solvent_exptl_crystal_recrystallization_method 'ethyl acetate'
_chemical_compound_source        Sigma
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TB-IL_295
_database_code_depnum_ccdc_archive 'CCDC 1469770'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(Butylcarbamoyl)-4-methylbenzenesulfonamide
_chemical_name_common            'Tolbutamide form IL'
_chemical_formula_moiety         'C12 H18 N2 O3 S'
_chemical_formula_sum            'C12 H18 N2 O3 S'
_exptl_crystal_recrystallization_method 
'from solution of tolbutamide in ethyl acetate'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      295(2)
_chemical_formula_weight         270.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P n a 21'
_symmetry_int_tables_number      33
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   20.2133(6)
_cell_length_b                   7.8233(2)
_cell_length_c                   9.0717(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1434.55(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    15524
_cell_measurement_theta_min      3.2834
_cell_measurement_theta_max      37.0874
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92362
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            26312
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.293
_diffrn_reflns_theta_max         26.354
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2924
_reflns_number_gt                2725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997) 
;
_computing_publication_material  
;
 SHELXL-2014/6 (Sheldrick, 2014), WinGX (Farrugia, 
 1999), Mercury (Macrae et al., 2008)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²+0.0923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1215 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.946(14)

_chemical_absolute_configuration unk
_refine_ls_number_reflns         2924
_refine_ls_number_parameters     165
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2537(3) 0.4899(7) 0.3457(9) 0.1044(19) Uani 1 1 d . . . . .
H1A H 0.2304 0.5518 0.4210 0.157 Uiso 1 1 calc R U . . .
H1B H 0.2560 0.5582 0.2580 0.157 Uiso 1 1 calc R U . . .
H1C H 0.2976 0.4643 0.3793 0.157 Uiso 1 1 calc R U . . .
C2 C 0.2177(2) 0.3266(5) 0.3129(5) 0.0714(11) Uani 1 1 d . . . . .
C3 C 0.2240(2) 0.1841(6) 0.4041(6) 0.0828(14) Uani 1 1 d . . . . .
H3 H 0.2526 0.1888 0.4842 0.099 Uiso 1 1 calc R U . . .
C4 C 0.1887(2) 0.0363(5) 0.3781(5) 0.0676(9) Uani 1 1 d . . . . .
H4 H 0.1927 -0.0568 0.4412 0.081 Uiso 1 1 calc R U . . .
C5 C 0.14746(16) 0.0284(4) 0.2578(3) 0.0494(7) Uani 1 1 d . . . . .
C6 C 0.1414(2) 0.1676(5) 0.1646(5) 0.0668(10) Uani 1 1 d . . . . .
H6 H 0.1138 0.1608 0.0828 0.080 Uiso 1 1 calc R U . . .
C7 C 0.1756(2) 0.3148(5) 0.1918(5) 0.0737(12) Uani 1 1 d . . . . .
H7 H 0.1707 0.4080 0.1290 0.088 Uiso 1 1 calc R U . . .
C8 C -0.00674(14) 0.0184(4) 0.2373(3) 0.0460(6) Uani 1 1 d . . . . .
C9 C -0.08483(18) 0.2530(4) 0.2185(4) 0.0625(8) Uani 1 1 d . . . . .
H9A H -0.1026 0.2181 0.3132 0.075 Uiso 1 1 calc R U . . .
H9B H -0.1218 0.2795 0.1542 0.075 Uiso 1 1 calc R U . . .
C10 C -0.0426(3) 0.4132(5) 0.2393(8) 0.0965(16) Uani 1 1 d . . . . .
H10A H -0.0271 0.4514 0.1436 0.116 Uiso 1 1 calc R U . . .
H10B H -0.0041 0.3841 0.2980 0.116 Uiso 1 1 calc R U . . .
C11 C -0.0796(4) 0.5611(7) 0.3146(9) 0.119(2) Uani 1 1 d D . . . .
H11A H -0.1020 0.5188 0.4018 0.143 Uiso 1 1 calc R U . . .
H11B H -0.0480 0.6474 0.3455 0.143 Uiso 1 1 calc R U . . .
C12 C -0.1276(6) 0.6373(11) 0.2155(17) 0.190(5) Uani 1 1 d D . . . .
H12A H -0.1637 0.5594 0.2008 0.285 Uiso 1 1 calc R U . . .
H12B H -0.1069 0.6614 0.1226 0.285 Uiso 1 1 calc R U . . .
H12C H -0.1440 0.7417 0.2577 0.285 Uiso 1 1 calc R U . . .
O1 O 0.13306(14) -0.2489(3) 0.0999(3) 0.0617(7) Uani 1 1 d . . . . .
O2 O 0.09609(13) -0.2516(3) 0.3575(3) 0.0586(6) Uani 1 1 d . . . . .
O3 O -0.00177(13) 0.0303(3) 0.3716(2) 0.0637(7) Uani 1 1 d . . . . .
S1 S 0.10391(3) -0.16195(8) 0.22231(8) 0.0469(2) Uani 1 1 d . . . . .
N1 N 0.03183(13) -0.0984(3) 0.1589(3) 0.0473(6) Uani 1 1 d . . . . .
H1 H 0.0177 -0.1377 0.0762 0.057 Uiso 1 1 calc R U . . .
N2 N -0.04697(14) 0.1118(4) 0.1553(3) 0.0533(6) Uani 1 1 d . . . . .
H2 H -0.0509 0.0890 0.0630 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.500(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.392(6) . ?
C2 C3 1.394(6) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(5) . ?
C5 S1 1.760(3) . ?
C6 C7 1.366(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O3 1.226(4) . ?
C8 N2 1.322(4) . ?
C8 N1 1.396(4) . ?
C9 N2 1.461(4) . ?
C9 C10 1.528(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.538(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.451(12) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
O1 S1 1.429(2) . ?
O2 S1 1.421(3) . ?
S1 N1 1.643(3) . ?
N1 H1 0.8600 . ?
N2 H2 0.8600 . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.1(4) . . ?
C7 C2 C1 120.6(4) . . ?
C3 C2 C1 121.3(4) . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 S1 119.1(3) . . ?
C6 C5 S1 120.6(3) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 120.5(4) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O3 C8 N2 124.6(3) . . ?
O3 C8 N1 120.7(3) . . ?
N2 C8 N1 114.7(2) . . ?
N2 C9 C10 112.1(3) . . ?
N2 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 113.6(5) . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 C10 111.0(8) . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 S1 O1 118.76(14) . . ?
O2 S1 N1 110.65(15) . . ?
O1 S1 N1 103.75(14) . . ?
O2 S1 C5 108.37(15) . . ?
O1 S1 C5 109.80(16) . . ?
N1 S1 C5 104.57(14) . . ?
C8 N1 S1 121.0(2) . . ?
C8 N1 H1 119.5 . . ?
S1 N1 H1 119.5 . . ?
C8 N2 C9 121.2(3) . . ?
C8 N2 H2 119.4 . . ?
C9 N2 H2 119.4 . . ?

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
C7 C2 C3 C4 -1.4(8) . . . . ?
C1 C2 C3 C4 177.0(5) . . . . ?
C2 C3 C4 C5 1.4(8) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C3 C4 C5 S1 178.5(4) . . . . ?
C4 C5 C6 C7 -0.8(6) . . . . ?
S1 C5 C6 C7 -179.6(3) . . . . ?
C5 C6 C7 C2 0.8(7) . . . . ?
C3 C2 C7 C6 0.3(7) . . . . ?
C1 C2 C7 C6 -178.0(5) . . . . ?
N2 C9 C10 C11 -176.4(5) . . . . ?
C9 C10 C11 C12 -72.5(9) . . . . ?
C4 C5 S1 O2 25.4(3) . . . . ?
C6 C5 S1 O2 -155.8(3) . . . . ?
C4 C5 S1 O1 -105.8(3) . . . . ?
C6 C5 S1 O1 73.0(3) . . . . ?
C4 C5 S1 N1 143.5(3) . . . . ?
C6 C5 S1 N1 -37.7(3) . . . . ?
O3 C8 N1 S1 -26.5(4) . . . . ?
N2 C8 N1 S1 153.0(2) . . . . ?
O2 S1 N1 C8 63.3(3) . . . . ?
O1 S1 N1 C8 -168.2(2) . . . . ?
C5 S1 N1 C8 -53.2(3) . . . . ?
O3 C8 N2 C9 6.7(5) . . . . ?
N1 C8 N2 C9 -172.8(3) . . . . ?
C10 C9 N2 C8 78.7(5) . . . . ?

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
N1 H1 O3 0.86 2.06 2.729(3) 133.7 2_554
N2 H2 O2 0.86 2.43 3.079(4) 132.2 2_554
N2 H2 O3 0.86 2.24 2.971(3) 142.8 2_554

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TB-IL_200
_database_code_depnum_ccdc_archive 'CCDC 1469771'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(Butylcarbamoyl)-4-methylbenzenesulfonamide
_chemical_name_common            'Tolbutamide form IL'
_chemical_formula_moiety         'C12 H18 N2 O3 S'
_chemical_formula_sum            'C12 H18 N2 O3 S'
_exptl_crystal_recrystallization_method 
'from solution of tolbutamide in ethyl acetate'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      200(2)
_chemical_formula_weight         270.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P n a 21'
_symmetry_int_tables_number      33
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.7525(3)
_cell_length_b                   7.7998(1)
_cell_length_c                   9.0583(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1395.57(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    11818
_cell_measurement_theta_min      3.0449
_cell_measurement_theta_max      28.1189

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            17224
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.051
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2857
_reflns_number_gt                2741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997) 
;
_computing_publication_material  
;
 SHELXL-2014/6 (Sheldrick, 2014), WinGX (Farrugia, 
 1999), Mercury (Macrae et al., 2008)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.994(17)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2857
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.25335(17) 0.4806(4) 0.3453(4) 0.0589(9) Uani 1 1 d . . . . .
H1A H 0.2713 0.5285 0.2533 0.088 Uiso 1 1 calc R U . . .
H1B H 0.2907 0.4590 0.4141 0.088 Uiso 1 1 calc R U . . .
H1C H 0.2216 0.5622 0.3897 0.088 Uiso 1 1 calc R U . . .
C2 C 0.21726(13) 0.3152(3) 0.3130(3) 0.0397(6) Uani 1 1 d . . . . .
C3 C 0.22347(15) 0.1749(3) 0.4063(3) 0.0455(7) Uani 1 1 d . . . . .
H3 H 0.2526 0.1818 0.4896 0.055 Uiso 1 1 calc R U . . .
C4 C 0.18779(13) 0.0246(3) 0.3799(3) 0.0370(5) Uani 1 1 d . . . . .
H4 H 0.1917 -0.0700 0.4454 0.044 Uiso 1 1 calc R U . . .
C5 C 0.14656(11) 0.0143(3) 0.2573(2) 0.0270(5) Uani 1 1 d . . . . .
C6 C 0.14046(13) 0.1527(3) 0.1607(3) 0.0365(5) Uani 1 1 d . . . . .
H6 H 0.1125 0.1443 0.0758 0.044 Uiso 1 1 calc R U . . .
C7 C 0.17558(14) 0.3021(3) 0.1900(3) 0.0408(7) Uani 1 1 d . . . . .
H7 H 0.1712 0.3971 0.1251 0.049 Uiso 1 1 calc R U . . .
C8 C -0.01014(10) 0.0090(2) 0.2360(2) 0.0253(4) Uani 1 1 d . . . . .
C9 C -0.08563(11) 0.2541(3) 0.2189(3) 0.0305(4) Uani 1 1 d . . . . .
H9A H -0.1054 0.2175 0.3143 0.037 Uiso 1 1 calc R U . . .
H9B H -0.1234 0.2858 0.1524 0.037 Uiso 1 1 calc R U . . .
C10 C -0.04110(14) 0.4101(3) 0.2442(3) 0.0414(6) Uani 1 1 d . . . . .
H10A H -0.0224 0.4484 0.1484 0.050 Uiso 1 1 calc R U . . .
H10B H -0.0026 0.3773 0.3083 0.050 Uiso 1 1 calc R U . . .
C11 C -0.07894(19) 0.5587(4) 0.3153(4) 0.0540(8) Uani 1 1 d . . . . .
H11A H -0.1019 0.5168 0.4055 0.065 Uiso 1 1 calc R U . . .
H11B H -0.0458 0.6471 0.3457 0.065 Uiso 1 1 calc R U . . .
C12 C -0.1303(2) 0.6394(5) 0.2165(7) 0.0880(12) Uani 1 1 d . . . . .
H12A H -0.1088 0.6728 0.1234 0.132 Uiso 1 1 calc R U . . .
H12B H -0.1492 0.7413 0.2647 0.132 Uiso 1 1 calc R U . . .
H12C H -0.1667 0.5573 0.1966 0.132 Uiso 1 1 calc R U . . .
O1 O 0.13163(9) -0.2655(2) 0.09963(17) 0.0341(4) Uani 1 1 d . . . . .
O2 O 0.09375(8) -0.2663(2) 0.35858(17) 0.0323(4) Uani 1 1 d . . . . .
O3 O -0.00666(9) 0.0151(2) 0.37238(18) 0.0354(4) Uani 1 1 d . . . . .
S1 S 0.10179(2) -0.17670(6) 0.22219(7) 0.02501(14) Uani 1 1 d . . . . .
N1 N 0.02785(10) -0.1130(2) 0.1581(2) 0.0252(4) Uani 1 1 d . . . . .
N2 N -0.04825(10) 0.1104(2) 0.1542(2) 0.0296(4) Uani 1 1 d . . . . .
H2 H -0.0426(14) 0.108(4) 0.066(4) 0.038(8) Uiso 1 1 d . . . . .
H1 H 0.0239(13) -0.109(4) 0.067(4) 0.033(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.503(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.388(4) . ?
C2 C7 1.389(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 S1 1.762(2) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O3 1.238(3) . ?
C8 N2 1.320(3) . ?
C8 N1 1.402(3) . ?
C9 N2 1.464(3) . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.522(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.492(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 S1 1.4353(16) . ?
O2 S1 1.4282(17) . ?
S1 N1 1.6481(19) . ?
N1 H1 0.83(3) . ?
N2 H2 0.81(3) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.9(2) . . ?
C3 C2 C1 121.1(2) . . ?
C7 C2 C1 120.1(3) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 S1 119.39(18) . . ?
C6 C5 S1 119.86(17) . . ?
C7 C6 C5 119.3(2) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 120.9(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
O3 C8 N2 124.7(2) . . ?
O3 C8 N1 119.89(19) . . ?
N2 C8 N1 115.5(2) . . ?
N2 C9 C10 112.43(18) . . ?
N2 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N2 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 C11 112.9(2) . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 113.7(3) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 S1 O1 118.59(9) . . ?
O2 S1 N1 110.70(10) . . ?
O1 S1 N1 103.71(10) . . ?
O2 S1 C5 108.27(10) . . ?
O1 S1 C5 109.99(10) . . ?
N1 S1 C5 104.68(10) . . ?
C8 N1 S1 120.11(16) . . ?
C8 N1 H1 115.3(19) . . ?
S1 N1 H1 116.3(19) . . ?
C8 N2 C9 121.43(19) . . ?
C8 N2 H2 118(2) . . ?
C9 N2 H2 119(2) . . ?

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
C7 C2 C3 C4 -1.3(4) . . . . ?
C1 C2 C3 C4 177.1(3) . . . . ?
C2 C3 C4 C5 1.2(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C5 S1 179.4(2) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
S1 C5 C6 C7 179.7(2) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
C3 C2 C7 C6 0.3(4) . . . . ?
C1 C2 C7 C6 -178.1(3) . . . . ?
N2 C9 C10 C11 -178.4(2) . . . . ?
C9 C10 C11 C12 -69.0(4) . . . . ?
C4 C5 S1 O2 23.9(2) . . . . ?
C6 C5 S1 O2 -156.57(19) . . . . ?
C4 C5 S1 O1 -107.08(19) . . . . ?
C6 C5 S1 O1 72.4(2) . . . . ?
C4 C5 S1 N1 142.06(19) . . . . ?
C6 C5 S1 N1 -38.5(2) . . . . ?
O3 C8 N1 S1 -31.6(3) . . . . ?
N2 C8 N1 S1 148.81(17) . . . . ?
O2 S1 N1 C8 65.16(18) . . . . ?
O1 S1 N1 C8 -166.61(16) . . . . ?
C5 S1 N1 C8 -51.28(19) . . . . ?
O3 C8 N2 C9 6.3(3) . . . . ?
N1 C8 N2 C9 -174.14(19) . . . . ?
C10 C9 N2 C8 80.2(3) . . . . ?

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
N1 H1 O3 0.83(3) 1.94(3) 2.731(3) 159(3) 2_554
N2 H2 O2 0.81(3) 2.46(3) 3.075(3) 134(3) 2_554
N2 H2 O3 0.81(3) 2.22(3) 2.942(3) 148(3) 2_554

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TB-IL_100
_database_code_depnum_ccdc_archive 'CCDC 1469772'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(Butylcarbamoyl)-4-methylbenzenesulfonamide
_chemical_name_common            'Tolbutamide form IL'
_chemical_formula_moiety         'C12 H18 N2 O3 S'
_chemical_formula_sum            'C12 H18 N2 O3 S'
_exptl_crystal_recrystallization_method 
'from solution of tolbutamide in ethyl acetate'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         270.34


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P n a 21'
_symmetry_int_tables_number      33
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   19.4331(3)
_cell_length_b                   7.8010(1)
_cell_length_c                   9.0277(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1368.58(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    28126
_cell_measurement_theta_min      3.3422
_cell_measurement_theta_max      37.1508

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95221
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            47528
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.349
_diffrn_reflns_theta_max         36.318
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6600
_reflns_number_gt                6147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
;
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 ORTEP-3 for Windows (Farrugia, 1997) 
;
_computing_publication_material  
;
 SHELXL-2014/6 (Sheldrick, 2014), WinGX (Farrugia, 
 1999), Mercury (Macrae et al., 2008)
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6600
_refine_ls_number_parameters     173
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0724
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.25233(8) 0.47835(18) 0.3490(2) 0.0316(3) Uani 1 1 d . . . . .
H1A H 0.2192 0.5603 0.3901 0.047 Uiso 1 1 calc R U . . .
H1B H 0.2721 0.5251 0.2577 0.047 Uiso 1 1 calc R U . . .
H1C H 0.2891 0.4580 0.4211 0.047 Uiso 1 1 calc R U . . .
C2 C 0.21632(7) 0.31199(15) 0.31534(15) 0.0206(2) Uani 1 1 d . . . . .
C3 C 0.22252(7) 0.17178(16) 0.41014(15) 0.0227(2) Uani 1 1 d . . . . .
H3 H 0.2515 0.1796 0.4946 0.027 Uiso 1 1 calc R U . . .
C4 C 0.18671(6) 0.02020(16) 0.38271(13) 0.0191(2) Uani 1 1 d . . . . .
H4 H 0.1906 -0.0742 0.4487 0.023 Uiso 1 1 calc R U . . .
C5 C 0.14538(6) 0.00903(14) 0.25774(11) 0.01456(17) Uani 1 1 d . . . . .
C6 C 0.13949(6) 0.14673(16) 0.15939(13) 0.01901(19) Uani 1 1 d . . . . .
H6 H 0.1118 0.1374 0.0731 0.023 Uiso 1 1 calc R U . . .
C7 C 0.17479(7) 0.29734(16) 0.18990(13) 0.0214(2) Uani 1 1 d . . . . .
H7 H 0.1706 0.3920 0.1243 0.026 Uiso 1 1 calc R U . . .
C8 C -0.01281(5) 0.00326(12) 0.23494(11) 0.01308(15) Uani 1 1 d . . . . .
C9 C -0.08768(5) 0.25236(13) 0.21765(13) 0.01601(16) Uani 1 1 d . . . . .
H9A H -0.1083 0.2149 0.3126 0.019 Uiso 1 1 calc R U . . .
H9B H -0.1256 0.2867 0.1506 0.019 Uiso 1 1 calc R U . . .
C10 C -0.04119(6) 0.40673(15) 0.24575(13) 0.0204(2) Uani 1 1 d . . . . .
H10A H -0.0026 0.3715 0.3105 0.024 Uiso 1 1 calc R U . . .
H10B H -0.0215 0.4458 0.1504 0.024 Uiso 1 1 calc R U . . .
C11 C -0.07949(9) 0.55548(17) 0.31829(17) 0.0273(3) Uani 1 1 d . . . . .
H11A H -0.1033 0.5129 0.4080 0.033 Uiso 1 1 calc R U . . .
H11B H -0.0456 0.6429 0.3500 0.033 Uiso 1 1 calc R U . . .
C12 C -0.13188(9) 0.6392(2) 0.2172(3) 0.0444(4) Uani 1 1 d . . . . .
H12A H -0.1094 0.6743 0.1249 0.067 Uiso 1 1 calc R U . . .
H12B H -0.1514 0.7400 0.2664 0.067 Uiso 1 1 calc R U . . .
H12C H -0.1687 0.5573 0.1949 0.067 Uiso 1 1 calc R U . . .
O1 O 0.13184(5) -0.27044(11) 0.09902(9) 0.01778(15) Uani 1 1 d . . . . .
O2 O 0.09229(4) -0.27237(11) 0.35891(9) 0.01683(15) Uani 1 1 d . . . . .
O3 O -0.01063(5) 0.00650(12) 0.37220(9) 0.01825(15) Uani 1 1 d . . . . .
S1 S 0.10067(2) -0.18248(3) 0.22182(3) 0.01277(5) Uani 1 1 d . . . . .
N1 N 0.02559(5) -0.11972(12) 0.15659(9) 0.01331(15) Uani 1 1 d . . . . .
N2 N -0.05019(5) 0.10883(13) 0.15167(10) 0.01547(16) Uani 1 1 d . . . . .
H2 H -0.0424(9) 0.109(2) 0.066(2) 0.020(4) Uiso 1 1 d . . . . .
H1 H 0.0231(10) -0.115(3) 0.070(2) 0.027(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
C1 C2 1.5054(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.3940(18) . ?
C2 C7 1.3953(17) . ?
C3 C4 1.3943(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3877(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3982(16) . ?
C5 S1 1.7584(11) . ?
C6 C7 1.3881(17) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 O3 1.2402(12) . ?
C8 N2 1.3308(13) . ?
C8 N1 1.4063(13) . ?
C9 N2 1.4626(14) . ?
C9 C10 1.5267(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5262(18) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 S1 1.4376(8) . ?
O2 S1 1.4318(9) . ?
S1 N1 1.6477(9) . ?
N1 H1 0.79(2) . ?
N2 H2 0.79(2) . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.95(11) . . ?
C3 C2 C1 120.81(12) . . ?
C7 C2 C1 120.22(12) . . ?
C2 C3 C4 120.88(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.11(11) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.02(11) . . ?
C4 C5 S1 119.29(9) . . ?
C6 C5 S1 119.68(8) . . ?
C7 C6 C5 118.94(11) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.08(11) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
O3 C8 N2 124.78(10) . . ?
O3 C8 N1 119.89(9) . . ?
N2 C8 N1 115.33(9) . . ?
N2 C9 C10 112.14(9) . . ?
N2 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 112.49(11) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 113.38(14) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 S1 O1 118.73(5) . . ?
O2 S1 N1 110.72(5) . . ?
O1 S1 N1 103.85(5) . . ?
O2 S1 C5 108.23(5) . . ?
O1 S1 C5 109.85(5) . . ?
N1 S1 C5 104.53(5) . . ?
C8 N1 S1 119.53(7) . . ?
C8 N1 H1 115.7(15) . . ?
S1 N1 H1 115.2(15) . . ?
C8 N2 C9 121.04(9) . . ?
C8 N2 H2 116.7(14) . . ?
C9 N2 H2 119.8(14) . . ?

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
C7 C2 C3 C4 -1.5(2) . . . . ?
C1 C2 C3 C4 177.04(14) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C4 C5 C6 0.27(18) . . . . ?
C3 C4 C5 S1 179.47(10) . . . . ?
C4 C5 C6 C7 -1.20(18) . . . . ?
S1 C5 C6 C7 179.60(10) . . . . ?
C5 C6 C7 C2 0.8(2) . . . . ?
C3 C2 C7 C6 0.5(2) . . . . ?
C1 C2 C7 C6 -178.00(13) . . . . ?
N2 C9 C10 C11 -178.52(10) . . . . ?
C9 C10 C11 C12 -68.58(16) . . . . ?
C4 C5 S1 O2 23.56(11) . . . . ?
C6 C5 S1 O2 -157.23(9) . . . . ?
C4 C5 S1 O1 -107.52(10) . . . . ?
C6 C5 S1 O1 71.70(10) . . . . ?
C4 C5 S1 N1 141.60(9) . . . . ?
C6 C5 S1 N1 -39.18(10) . . . . ?
O3 C8 N1 S1 -33.80(14) . . . . ?
N2 C8 N1 S1 146.82(8) . . . . ?
O2 S1 N1 C8 65.67(9) . . . . ?
O1 S1 N1 C8 -165.83(8) . . . . ?
C5 S1 N1 C8 -50.66(9) . . . . ?
O3 C8 N2 C9 6.19(17) . . . . ?
N1 C8 N2 C9 -174.46(9) . . . . ?
C10 C9 N2 C8 81.09(13) . . . . ?

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
N1 H1 O3 0.79(2) 1.99(2) 2.7306(12) 157(2) 2_554
N2 H2 O2 0.79(2) 2.460(19) 3.0467(13) 131.9(17) 2_554
N2 H2 O3 0.79(2) 2.218(19) 2.9277(12) 149.6(18) 2_554

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TB-II_100
_database_code_depnum_ccdc_archive 'CCDC 1469773'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        N-(Butylcarbamoyl)-4-methylbenzenesulfonamide
_chemical_name_common            'Tolbutamide form II'
_chemical_formula_moiety         'C12 H18 N2 O3 S'
_chemical_formula_sum            'C12 H18 N2 O3 S'
_exptl_crystal_recrystallization_method 
'from solution of tolbutamide in acetonitrile'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         270.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P c'
_symmetry_int_tables_number      7
_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   9.0256(2)
_cell_length_b                   17.1443(5)
_cell_length_c                   17.7904(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.268(3)
_cell_angle_gamma                90
_cell_volume                     2745.21(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7205
_cell_measurement_theta_min      3.0870
_cell_measurement_theta_max      23.3680

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
(compiled Sep 15 2009,11:49:04)
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number            42260
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.102
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11214
_reflns_number_gt                8469
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.0936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3118 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         11214
_refine_ls_number_parameters     657
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S1A S 0.92184(14) 0.04470(9) 0.24387(8) 0.0189(3) Uani 1 1 d . . . . .
S1C S 0.94058(15) 0.53562(9) 0.56552(8) 0.0212(3) Uani 1 1 d . . . . .
S1D S 0.40731(14) 0.56244(9) 0.28378(8) 0.0179(3) Uani 1 1 d . . . . .
S1B S 0.38783(15) 0.09154(8) 0.49125(8) 0.0196(3) Uani 1 1 d . . . . .
O3A O 0.6348(4) 0.0479(2) 0.3131(2) 0.0213(9) Uani 1 1 d . . . . .
O2C O 1.0849(4) 0.5662(2) 0.5841(2) 0.0261(10) Uani 1 1 d . . . . .
O2A O 0.9483(4) 0.0041(2) 0.3139(2) 0.0243(9) Uani 1 1 d . . . . .
O2B O 0.3593(4) 0.0485(2) 0.5576(2) 0.0229(9) Uani 1 1 d . . . . .
O1C O 0.8260(4) 0.5501(2) 0.6152(2) 0.0264(10) Uani 1 1 d . . . . .
O3B O 0.6765(4) 0.0416(2) 0.5707(2) 0.0228(9) Uani 1 1 d . . . . .
O3D O 0.5821(4) 0.5846(2) 0.4333(2) 0.0257(10) Uani 1 1 d . . . . .
O3C O 1.0810(4) 0.5615(2) 0.4207(2) 0.0267(10) Uani 1 1 d . . . . .
O1D O 0.2829(4) 0.5839(2) 0.2338(2) 0.0227(9) Uani 1 1 d . . . . .
O1A O 1.0131(4) 0.0295(2) 0.1831(2) 0.0271(10) Uani 1 1 d . . . . .
C8C C 0.9454(6) 0.5723(3) 0.4188(3) 0.0187(13) Uani 1 1 d . . . . .
O2D O 0.5494(4) 0.5970(2) 0.2763(2) 0.0221(9) Uani 1 1 d . . . . .
N1B N 0.5415(5) 0.0605(3) 0.4582(2) 0.0214(11) Uani 1 1 d . . . . .
H1B H 0.5423 0.0563 0.4090 0.026 Uiso 1 1 calc R U . . .
C8D C 0.4458(6) 0.5914(3) 0.4334(3) 0.0169(13) Uani 1 1 d . . . . .
O1B O 0.2822(4) 0.0900(2) 0.4266(2) 0.0266(10) Uani 1 1 d . . . . .
N1C N 0.8708(5) 0.5708(3) 0.4846(3) 0.0227(11) Uani 1 1 d . . . . .
H1C H 0.7802 0.5901 0.4827 0.027 Uiso 1 1 calc R U . . .
N2C N 0.8585(5) 0.5865(3) 0.3566(3) 0.0201(11) Uani 1 1 d . . . . .
H2C H 0.7614 0.5873 0.3589 0.024 Uiso 1 1 calc R U . . .
C5C C 0.9530(6) 0.4345(3) 0.5523(3) 0.0214(14) Uani 1 1 d . . . . .
N2D N 0.3753(5) 0.6079(3) 0.4945(3) 0.0180(10) Uani 1 1 d . . . . .
H2D H 0.2775 0.6068 0.4918 0.022 Uiso 1 1 calc R U . . .
N2A N 0.5060(4) 0.0007(3) 0.2077(2) 0.0182(11) Uani 1 1 d . . . . .
H2A H 0.5130 -0.0144 0.1608 0.022 Uiso 1 1 calc R U . . .
N2B N 0.7837(5) 0.0203(3) 0.4605(3) 0.0223(11) Uani 1 1 d . . . . .
H2B H 0.7761 0.0301 0.4118 0.027 Uiso 1 1 calc R U . . .
N1D N 0.3533(5) 0.5830(3) 0.3675(2) 0.0202(11) Uani 1 1 d . . . . .
H1D H 0.2573 0.5893 0.3712 0.024 Uiso 1 1 calc R U . . .
C8A C 0.6265(6) 0.0259(3) 0.2469(3) 0.0178(12) Uani 1 1 d . . . . .
C5D C 0.4265(6) 0.4601(3) 0.2810(3) 0.0187(13) Uani 1 1 d . . . . .
C9C C 0.9221(6) 0.6009(3) 0.2842(3) 0.0223(14) Uani 1 1 d . . . . .
H9CA H 0.8481 0.5869 0.2425 0.027 Uiso 1 1 calc R U . . .
H9CB H 1.0103 0.5672 0.2805 0.027 Uiso 1 1 calc R U . . .
C5A C 0.9266(6) 0.1454(3) 0.2643(3) 0.0170(13) Uani 1 1 d . . . . .
C7C C 0.8413(7) 0.3131(4) 0.5144(4) 0.0367(17) Uani 1 1 d . . . . .
H7C H 0.7606 0.2851 0.4901 0.044 Uiso 1 1 calc R U . . .
C8B C 0.6717(6) 0.0402(3) 0.5013(3) 0.0182(13) Uani 1 1 d . . . . .
N1A N 0.7538(4) 0.0273(3) 0.2066(2) 0.0173(11) Uani 1 1 d . . . . .
H1A H 0.7428 0.0182 0.1578 0.021 Uiso 1 1 calc R U . . .
C9D C 0.4569(6) 0.6279(3) 0.5659(3) 0.0210(13) Uani 1 1 d . . . . .
H9DA H 0.5386 0.5900 0.5763 0.025 Uiso 1 1 calc R U . . .
H9DB H 0.3893 0.6238 0.6071 0.025 Uiso 1 1 calc R U . . .
C4A C 0.9923(6) 0.1703(4) 0.3328(3) 0.0244(14) Uani 1 1 d . . . . .
H4A H 1.0289 0.1335 0.3697 0.029 Uiso 1 1 calc R U . . .
C6D C 0.3094(6) 0.4161(4) 0.2490(3) 0.0258(14) Uani 1 1 d . . . . .
H6D H 0.2209 0.4406 0.2286 0.031 Uiso 1 1 calc R U . . .
C3C C 1.0801(7) 0.3143(4) 0.5812(3) 0.0316(16) Uani 1 1 d . . . . .
H3C H 1.1648 0.2876 0.6032 0.038 Uiso 1 1 calc R U . . .
C4D C 0.5546(6) 0.4250(4) 0.3115(3) 0.0257(14) Uani 1 1 d . . . . .
H4D H 0.6343 0.4557 0.3333 0.031 Uiso 1 1 calc R U . . .
C9B C 0.9184(6) -0.0169(4) 0.4933(4) 0.0286(15) Uani 1 1 d . . . . .
H9BB H 0.9394 0.0010 0.5459 0.034 Uiso 1 1 calc R U . . .
H9BA H 1.0037 -0.0024 0.4643 0.034 Uiso 1 1 calc R U . . .
C4C C 1.0756(6) 0.3946(4) 0.5837(3) 0.0259(14) Uani 1 1 d . . . . .
H4C H 1.1572 0.4227 0.6072 0.031 Uiso 1 1 calc R U . . .
C2C C 0.9636(7) 0.2718(4) 0.5472(4) 0.0303(15) Uani 1 1 d . . . . .
C5B C 0.4186(6) 0.1894(3) 0.5177(3) 0.0202(14) Uani 1 1 d . . . . .
C9A C 0.3606(6) -0.0033(3) 0.2397(3) 0.0210(13) Uani 1 1 d . . . . .
H9AA H 0.2838 0.0185 0.2029 0.025 Uiso 1 1 calc R U . . .
H9AB H 0.3631 0.0293 0.2857 0.025 Uiso 1 1 calc R U . . .
C6A C 0.8744(6) 0.1996(4) 0.2099(3) 0.0246(14) Uani 1 1 d . . . . .
H6A H 0.8316 0.1827 0.1623 0.030 Uiso 1 1 calc R U . . .
C3A C 1.0039(6) 0.2492(4) 0.3468(3) 0.0238(14) Uani 1 1 d . . . . .
H3A H 1.0495 0.2663 0.3938 0.029 Uiso 1 1 calc R U . . .
C6C C 0.8352(6) 0.3931(4) 0.5165(3) 0.0276(15) Uani 1 1 d . . . . .
H6C H 0.7514 0.4199 0.4937 0.033 Uiso 1 1 calc R U . . .
C2A C 0.9517(6) 0.3038(4) 0.2951(3) 0.0208(14) Uani 1 1 d . . . . .
C4B C 0.4796(6) 0.2089(3) 0.5892(3) 0.0227(14) Uani 1 1 d . . . . .
H4B H 0.5064 0.1690 0.6247 0.027 Uiso 1 1 calc R U . . .
C2D C 0.4503(7) 0.2989(4) 0.2776(4) 0.0296(15) Uani 1 1 d . . . . .
C3B C 0.5011(6) 0.2861(4) 0.6085(3) 0.0242(14) Uani 1 1 d . . . . .
H3B H 0.5415 0.2990 0.6578 0.029 Uiso 1 1 calc R U . . .
C2B C 0.4646(6) 0.3456(3) 0.5569(3) 0.0267(15) Uani 1 1 d . . . . .
C1B C 0.4872(7) 0.4297(4) 0.5766(4) 0.0326(16) Uani 1 1 d . . . . .
H1BC H 0.5754 0.4353 0.6118 0.049 Uiso 1 1 calc R U . . .
H1BB H 0.3999 0.4495 0.6002 0.049 Uiso 1 1 calc R U . . .
H1BA H 0.5012 0.4596 0.5307 0.049 Uiso 1 1 calc R U . . .
C7B C 0.4050(7) 0.3248(4) 0.4850(4) 0.0281(15) Uani 1 1 d . . . . .
H7B H 0.3801 0.3645 0.4490 0.034 Uiso 1 1 calc R U . . .
C7D C 0.3237(7) 0.3356(4) 0.2471(4) 0.0309(16) Uani 1 1 d . . . . .
H7D H 0.2447 0.3051 0.2245 0.037 Uiso 1 1 calc R U . . .
C6B C 0.3814(6) 0.2479(3) 0.4653(3) 0.0231(14) Uani 1 1 d . . . . .
H6B H 0.3401 0.2348 0.4162 0.028 Uiso 1 1 calc R U . . .
C7A C 0.8860(6) 0.2772(3) 0.2265(3) 0.0261(15) Uani 1 1 d . . . . .
H7A H 0.8483 0.3142 0.1901 0.031 Uiso 1 1 calc R U . . .
C1A C 0.9595(7) 0.3892(4) 0.3135(4) 0.0304(16) Uani 1 1 d . . . . .
H1AC H 1.0601 0.4023 0.3342 0.046 Uiso 1 1 calc R U . . .
H1AB H 0.8883 0.4014 0.3508 0.046 Uiso 1 1 calc R U . . .
H1AA H 0.9353 0.4196 0.2676 0.046 Uiso 1 1 calc R U . . .
C1C C 0.9660(9) 0.1843(4) 0.5451(4) 0.049(2) Uani 1 1 d . . . . .
H1CB H 0.8897 0.1638 0.5761 0.073 Uiso 1 1 calc R U . . .
H1CC H 1.0639 0.1656 0.5647 0.073 Uiso 1 1 calc R U . . .
H1CA H 0.9459 0.1665 0.4930 0.073 Uiso 1 1 calc R U . . .
C1D C 0.4671(8) 0.2118(4) 0.2741(4) 0.0430(19) Uani 1 1 d . . . . .
H1DB H 0.4986 0.1969 0.2245 0.064 Uiso 1 1 calc R U . . .
H1DA H 0.3717 0.1870 0.2820 0.064 Uiso 1 1 calc R U . . .
H1DC H 0.5419 0.1948 0.3134 0.064 Uiso 1 1 calc R U . . .
C10A C 0.3178(6) -0.0867(4) 0.2594(4) 0.0293(15) Uani 1 1 d . . . . .
H10G H 0.2171 -0.0862 0.2780 0.035 Uiso 1 1 calc R U . . .
H10H H 0.3136 -0.1187 0.2130 0.035 Uiso 1 1 calc R U . . .
C3D C 0.5657(7) 0.3453(4) 0.3101(4) 0.0316(16) Uani 1 1 d . . . . .
H3D H 0.6534 0.3210 0.3316 0.038 Uiso 1 1 calc R U . . .
C12B C 0.9956(9) -0.2398(4) 0.5080(5) 0.062(2) Uani 1 1 d . . . . .
H12A H 0.9621 -0.2514 0.4555 0.093 Uiso 1 1 calc R U . . .
H12B H 0.9173 -0.2538 0.5408 0.093 Uiso 1 1 calc R U . . .
H12C H 1.0855 -0.2699 0.5225 0.093 Uiso 1 1 calc R U . . .
C10D C 0.5213(7) 0.7099(3) 0.5654(4) 0.0271(14) Uani 1 1 d . . . . .
H10F H 0.5823 0.7184 0.6133 0.033 Uiso 1 1 calc R U . . .
H10E H 0.5881 0.7137 0.5239 0.033 Uiso 1 1 calc R U . . .
C12C C 0.8803(9) 0.8244(4) 0.2588(5) 0.065(3) Uani 1 1 d . . . . .
H12E H 0.9415 0.8311 0.2160 0.098 Uiso 1 1 calc R U . . .
H12F H 0.9374 0.8399 0.3054 0.098 Uiso 1 1 calc R U . . .
H12D H 0.7912 0.8571 0.2515 0.098 Uiso 1 1 calc R U . . .
C11C C 0.8348(8) 0.7396(4) 0.2643(5) 0.057(2) Uani 1 1 d . . . . .
H11B H 0.7710 0.7334 0.3069 0.068 Uiso 1 1 calc R U . . .
H11A H 0.7757 0.7244 0.2175 0.068 Uiso 1 1 calc R U . . .
C11A C 0.4242(7) -0.1245(4) 0.3183(4) 0.0410(18) Uani 1 1 d . . . . .
H11G H 0.4251 -0.0941 0.3657 0.049 Uiso 1 1 calc R U . . .
H11H H 0.5258 -0.1233 0.3009 0.049 Uiso 1 1 calc R U . . .
C10C C 0.9672(6) 0.6862(4) 0.2761(4) 0.0312(16) Uani 1 1 d . . . . .
H10B H 1.0280 0.7025 0.3220 0.037 Uiso 1 1 calc R U . . .
H10A H 1.0292 0.6912 0.2327 0.037 Uiso 1 1 calc R U . . .
C12A C 0.3819(8) -0.2086(4) 0.3341(4) 0.049(2) Uani 1 1 d . . . . .
H12K H 0.3749 -0.2382 0.2869 0.073 Uiso 1 1 calc R U . . .
H12J H 0.2858 -0.2097 0.3563 0.073 Uiso 1 1 calc R U . . .
H12L H 0.4579 -0.2321 0.3693 0.073 Uiso 1 1 calc R U . . .
C12D C 0.4770(9) 0.8553(4) 0.5521(4) 0.047(2) Uani 1 1 d . . . . .
H12G H 0.5405 0.8571 0.5098 0.071 Uiso 1 1 calc R U . . .
H12I H 0.5370 0.8659 0.5992 0.071 Uiso 1 1 calc R U . . .
H12H H 0.3987 0.8948 0.5447 0.071 Uiso 1 1 calc R U . . .
C11D C 0.4063(7) 0.7743(3) 0.5560(4) 0.0306(15) Uani 1 1 d . . . . .
H11F H 0.3426 0.7727 0.5989 0.037 Uiso 1 1 calc R U . . .
H11E H 0.3421 0.7650 0.5093 0.037 Uiso 1 1 calc R U . . .
C11B C 1.0295(8) -0.1531(4) 0.5160(5) 0.055(2) Uani 1 1 d . . . . .
H11D H 1.0608 -0.1408 0.5692 0.066 Uiso 1 1 calc R U . . .
H11C H 1.1120 -0.1391 0.4848 0.066 Uiso 1 1 calc R U . . .
C10B C 0.8969(8) -0.1076(4) 0.4917(5) 0.049(2) Uani 1 1 d . . . . .
H10D H 0.8168 -0.1211 0.5245 0.059 Uiso 1 1 calc R U . . .
H10C H 0.8633 -0.1233 0.4396 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S1A O1A 1.430(4) . ?
S1A O2A 1.431(4) . ?
S1A N1A 1.637(4) . ?
S1A C5A 1.765(6) . ?
S1C O2C 1.420(4) . ?
S1C O1C 1.432(4) . ?
S1C N1C 1.642(5) . ?
S1C C5C 1.755(6) . ?
S1D O2D 1.428(4) . ?
S1D O1D 1.428(4) . ?
S1D N1D 1.640(5) . ?
S1D C5D 1.765(6) . ?
S1B O2B 1.431(4) . ?
S1B O1B 1.439(4) . ?
S1B N1B 1.635(5) . ?
S1B C5B 1.759(6) . ?
O3A C8A 1.234(6) . ?
O3B C8B 1.233(6) . ?
O3D C8D 1.236(6) . ?
O3C C8C 1.236(6) . ?
C8C N2C 1.330(7) . ?
C8C N1C 1.394(7) . ?
N1B C8B 1.399(6) . ?
N1B H1B 0.8800 . ?
C8D N2D 1.331(7) . ?
C8D N1D 1.395(7) . ?
N1C H1C 0.8800 . ?
N2C C9C 1.469(7) . ?
N2C H2C 0.8800 . ?
C5C C4C 1.382(8) . ?
C5C C6C 1.393(8) . ?
N2D C9D 1.461(7) . ?
N2D H2D 0.8800 . ?
N2A C8A 1.320(7) . ?
N2A C9A 1.471(7) . ?
N2A H2A 0.8800 . ?
N2B C8B 1.332(7) . ?
N2B C9B 1.456(7) . ?
N2B H2B 0.8800 . ?
N1D H1D 0.8800 . ?
C8A N1A 1.399(7) . ?
C5D C4D 1.378(8) . ?
C5D C6D 1.386(8) . ?
C9C C10C 1.528(9) . ?
C9C H9CA 0.9900 . ?
C9C H9CB 0.9900 . ?
C5A C4A 1.382(8) . ?
C5A C6A 1.398(8) . ?
C7C C6C 1.373(9) . ?
C7C C2C 1.401(9) . ?
C7C H7C 0.9500 . ?
N1A H1A 0.8800 . ?
C9D C10D 1.521(8) . ?
C9D H9DA 0.9900 . ?
C9D H9DB 0.9900 . ?
C4A C3A 1.378(8) . ?
C4A H4A 0.9500 . ?
C6D C7D 1.386(8) . ?
C6D H6D 0.9500 . ?
C3C C4C 1.379(9) . ?
C3C C2C 1.381(8) . ?
C3C H3C 0.9500 . ?
C4D C3D 1.371(8) . ?
C4D H4D 0.9500 . ?
C9B C10B 1.566(9) . ?
C9B H9BB 0.9900 . ?
C9B H9BA 0.9900 . ?
C4C H4C 0.9500 . ?
C2C C1C 1.500(9) . ?
C5B C4B 1.388(7) . ?
C5B C6B 1.393(8) . ?
C9A C10A 1.528(8) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C6A C7A 1.365(8) . ?
C6A H6A 0.9500 . ?
C3A C2A 1.371(8) . ?
C3A H3A 0.9500 . ?
C6C H6C 0.9500 . ?
C2A C7A 1.393(8) . ?
C2A C1A 1.502(8) . ?
C4B C3B 1.378(8) . ?
C4B H4B 0.9500 . ?
C2D C7D 1.379(9) . ?
C2D C3D 1.400(9) . ?
C2D C1D 1.502(9) . ?
C3B C2B 1.395(8) . ?
C3B H3B 0.9500 . ?
C2B C7B 1.397(8) . ?
C2B C1B 1.494(8) . ?
C1B H1BC 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BA 0.9800 . ?
C7B C6B 1.377(8) . ?
C7B H7B 0.9500 . ?
C7D H7D 0.9500 . ?
C6B H6B 0.9500 . ?
C7A H7A 0.9500 . ?
C1A H1AC 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AA 0.9800 . ?
C1C H1CB 0.9800 . ?
C1C H1CC 0.9800 . ?
C1C H1CA 0.9800 . ?
C1D H1DB 0.9800 . ?
C1D H1DA 0.9800 . ?
C1D H1DC 0.9800 . ?
C10A C11A 1.514(8) . ?
C10A H10G 0.9900 . ?
C10A H10H 0.9900 . ?
C3D H3D 0.9500 . ?
C12B C11B 1.522(10) . ?
C12B H12A 0.9800 . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C10D C11D 1.517(8) . ?
C10D H10F 0.9900 . ?
C10D H10E 0.9900 . ?
C12C C11C 1.517(10) . ?
C12C H12E 0.9800 . ?
C12C H12F 0.9800 . ?
C12C H12D 0.9800 . ?
C11C C10C 1.508(9) . ?
C11C H11B 0.9900 . ?
C11C H11A 0.9900 . ?
C11A C12A 1.523(9) . ?
C11A H11G 0.9900 . ?
C11A H11H 0.9900 . ?
C10C H10B 0.9900 . ?
C10C H10A 0.9900 . ?
C12A H12K 0.9800 . ?
C12A H12J 0.9800 . ?
C12A H12L 0.9800 . ?
C12D C11D 1.533(9) . ?
C12D H12G 0.9800 . ?
C12D H12I 0.9800 . ?
C12D H12H 0.9800 . ?
C11D H11F 0.9900 . ?
C11D H11E 0.9900 . ?
C11B C10B 1.467(9) . ?
C11B H11D 0.9900 . ?
C11B H11C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B H10C 0.9900 . ?

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
O1A S1A O2A 120.0(2) . . ?
O1A S1A N1A 103.2(2) . . ?
O2A S1A N1A 110.7(2) . . ?
O1A S1A C5A 109.1(3) . . ?
O2A S1A C5A 107.3(3) . . ?
N1A S1A C5A 105.7(2) . . ?
O2C S1C O1C 119.0(2) . . ?
O2C S1C N1C 110.7(2) . . ?
O1C S1C N1C 103.3(2) . . ?
O2C S1C C5C 109.2(3) . . ?
O1C S1C C5C 108.1(3) . . ?
N1C S1C C5C 105.7(3) . . ?
O2D S1D O1D 120.3(2) . . ?
O2D S1D N1D 109.0(2) . . ?
O1D S1D N1D 103.7(2) . . ?
O2D S1D C5D 108.6(3) . . ?
O1D S1D C5D 108.2(2) . . ?
N1D S1D C5D 106.0(3) . . ?
O2B S1B O1B 120.1(2) . . ?
O2B S1B N1B 109.8(2) . . ?
O1B S1B N1B 103.7(2) . . ?
O2B S1B C5B 107.8(3) . . ?
O1B S1B C5B 108.3(3) . . ?
N1B S1B C5B 106.6(3) . . ?
O3C C8C N2C 124.8(5) . . ?
O3C C8C N1C 121.0(5) . . ?
N2C C8C N1C 114.2(5) . . ?
C8B N1B S1B 125.8(4) . . ?
C8B N1B H1B 117.1 . . ?
S1B N1B H1B 117.1 . . ?
O3D C8D N2D 123.9(5) . . ?
O3D C8D N1D 121.5(5) . . ?
N2D C8D N1D 114.6(4) . . ?
C8C N1C S1C 124.4(4) . . ?
C8C N1C H1C 117.8 . . ?
S1C N1C H1C 117.8 . . ?
C8C N2C C9C 121.0(5) . . ?
C8C N2C H2C 119.5 . . ?
C9C N2C H2C 119.5 . . ?
C4C C5C C6C 119.6(6) . . ?
C4C C5C S1C 119.5(4) . . ?
C6C C5C S1C 120.7(5) . . ?
C8D N2D C9D 121.3(5) . . ?
C8D N2D H2D 119.3 . . ?
C9D N2D H2D 119.3 . . ?
C8A N2A C9A 122.4(5) . . ?
C8A N2A H2A 118.8 . . ?
C9A N2A H2A 118.8 . . ?
C8B N2B C9B 122.6(5) . . ?
C8B N2B H2B 118.7 . . ?
C9B N2B H2B 118.7 . . ?
C8D N1D S1D 125.8(4) . . ?
C8D N1D H1D 117.1 . . ?
S1D N1D H1D 117.1 . . ?
O3A C8A N2A 126.4(5) . . ?
O3A C8A N1A 119.3(5) . . ?
N2A C8A N1A 114.3(5) . . ?
C4D C5D C6D 121.1(6) . . ?
C4D C5D S1D 120.2(4) . . ?
C6D C5D S1D 118.6(4) . . ?
N2C C9C C10C 111.6(5) . . ?
N2C C9C H9CA 109.3 . . ?
C10C C9C H9CA 109.3 . . ?
N2C C9C H9CB 109.3 . . ?
C10C C9C H9CB 109.3 . . ?
H9CA C9C H9CB 108.0 . . ?
C4A C5A C6A 120.4(5) . . ?
C4A C5A S1A 119.0(4) . . ?
C6A C5A S1A 120.4(4) . . ?
C6C C7C C2C 121.7(6) . . ?
C6C C7C H7C 119.2 . . ?
C2C C7C H7C 119.2 . . ?
O3B C8B N2B 125.4(5) . . ?
O3B C8B N1B 120.6(5) . . ?
N2B C8B N1B 114.0(5) . . ?
C8A N1A S1A 124.6(4) . . ?
C8A N1A H1A 117.7 . . ?
S1A N1A H1A 117.7 . . ?
N2D C9D C10D 112.3(5) . . ?
N2D C9D H9DA 109.1 . . ?
C10D C9D H9DA 109.1 . . ?
N2D C9D H9DB 109.1 . . ?
C10D C9D H9DB 109.1 . . ?
H9DA C9D H9DB 107.9 . . ?
C3A C4A C5A 118.9(5) . . ?
C3A C4A H4A 120.6 . . ?
C5A C4A H4A 120.6 . . ?
C5D C6D C7D 118.8(6) . . ?
C5D C6D H6D 120.6 . . ?
C7D C6D H6D 120.6 . . ?
C4C C3C C2C 121.2(6) . . ?
C4C C3C H3C 119.4 . . ?
C2C C3C H3C 119.4 . . ?
C3D C4D C5D 119.1(6) . . ?
C3D C4D H4D 120.4 . . ?
C5D C4D H4D 120.4 . . ?
N2B C9B C10B 109.2(5) . . ?
N2B C9B H9BB 109.8 . . ?
C10B C9B H9BB 109.8 . . ?
N2B C9B H9BA 109.8 . . ?
C10B C9B H9BA 109.8 . . ?
H9BB C9B H9BA 108.3 . . ?
C3C C4C C5C 120.3(6) . . ?
C3C C4C H4C 119.8 . . ?
C5C C4C H4C 119.8 . . ?
C3C C2C C7C 117.8(6) . . ?
C3C C2C C1C 121.7(6) . . ?
C7C C2C C1C 120.5(6) . . ?
C4B C5B C6B 120.0(5) . . ?
C4B C5B S1B 121.2(5) . . ?
C6B C5B S1B 118.8(4) . . ?
N2A C9A C10A 112.3(5) . . ?
N2A C9A H9AA 109.1 . . ?
C10A C9A H9AA 109.1 . . ?
N2A C9A H9AB 109.1 . . ?
C10A C9A H9AB 109.1 . . ?
H9AA C9A H9AB 107.9 . . ?
C7A C6A C5A 118.8(5) . . ?
C7A C6A H6A 120.6 . . ?
C5A C6A H6A 120.6 . . ?
C2A C3A C4A 122.1(5) . . ?
C2A C3A H3A 118.9 . . ?
C4A C3A H3A 118.9 . . ?
C7C C6C C5C 119.4(6) . . ?
C7C C6C H6C 120.3 . . ?
C5C C6C H6C 120.3 . . ?
C3A C2A C7A 117.9(6) . . ?
C3A C2A C1A 120.7(5) . . ?
C7A C2A C1A 121.3(5) . . ?
C3B C4B C5B 119.9(5) . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B H4B 120.1 . . ?
C7D C2D C3D 118.2(6) . . ?
C7D C2D C1D 121.3(6) . . ?
C3D C2D C1D 120.5(6) . . ?
C4B C3B C2B 121.1(5) . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B H3B 119.5 . . ?
C3B C2B C7B 118.1(6) . . ?
C3B C2B C1B 122.0(6) . . ?
C7B C2B C1B 119.9(6) . . ?
C2B C1B H1BC 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
H1BC C1B H1BB 109.5 . . ?
C2B C1B H1BA 109.5 . . ?
H1BC C1B H1BA 109.5 . . ?
H1BB C1B H1BA 109.5 . . ?
C6B C7B C2B 121.4(6) . . ?
C6B C7B H7B 119.3 . . ?
C2B C7B H7B 119.3 . . ?
C2D C7D C6D 121.4(6) . . ?
C2D C7D H7D 119.3 . . ?
C6D C7D H7D 119.3 . . ?
C7B C6B C5B 119.5(5) . . ?
C7B C6B H6B 120.2 . . ?
C5B C6B H6B 120.2 . . ?
C6A C7A C2A 121.9(5) . . ?
C6A C7A H7A 119.0 . . ?
C2A C7A H7A 119.0 . . ?
C2A C1A H1AC 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AC C1A H1AB 109.5 . . ?
C2A C1A H1AA 109.5 . . ?
H1AC C1A H1AA 109.5 . . ?
H1AB C1A H1AA 109.5 . . ?
C2C C1C H1CB 109.5 . . ?
C2C C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
C2C C1C H1CA 109.5 . . ?
H1CB C1C H1CA 109.5 . . ?
H1CC C1C H1CA 109.5 . . ?
C2D C1D H1DB 109.5 . . ?
C2D C1D H1DA 109.5 . . ?
H1DB C1D H1DA 109.5 . . ?
C2D C1D H1DC 109.5 . . ?
H1DB C1D H1DC 109.5 . . ?
H1DA C1D H1DC 109.5 . . ?
C11A C10A C9A 113.7(5) . . ?
C11A C10A H10G 108.8 . . ?
C9A C10A H10G 108.8 . . ?
C11A C10A H10H 108.8 . . ?
C9A C10A H10H 108.8 . . ?
H10G C10A H10H 107.7 . . ?
C4D C3D C2D 121.4(6) . . ?
C4D C3D H3D 119.3 . . ?
C2D C3D H3D 119.3 . . ?
C11B C12B H12A 109.5 . . ?
C11B C12B H12B 109.5 . . ?
H12A C12B H12B 109.5 . . ?
C11B C12B H12C 109.5 . . ?
H12A C12B H12C 109.5 . . ?
H12B C12B H12C 109.5 . . ?
C11D C10D C9D 114.5(5) . . ?
C11D C10D H10F 108.6 . . ?
C9D C10D H10F 108.6 . . ?
C11D C10D H10E 108.6 . . ?
C9D C10D H10E 108.6 . . ?
H10F C10D H10E 107.6 . . ?
C11C C12C H12E 109.5 . . ?
C11C C12C H12F 109.5 . . ?
H12E C12C H12F 109.5 . . ?
C11C C12C H12D 109.5 . . ?
H12E C12C H12D 109.5 . . ?
H12F C12C H12D 109.5 . . ?
C10C C11C C12C 112.1(6) . . ?
C10C C11C H11B 109.2 . . ?
C12C C11C H11B 109.2 . . ?
C10C C11C H11A 109.2 . . ?
C12C C11C H11A 109.2 . . ?
H11B C11C H11A 107.9 . . ?
C10A C11A C12A 112.3(5) . . ?
C10A C11A H11G 109.2 . . ?
C12A C11A H11G 109.2 . . ?
C10A C11A H11H 109.2 . . ?
C12A C11A H11H 109.2 . . ?
H11G C11A H11H 107.9 . . ?
C11C C10C C9C 112.4(5) . . ?
C11C C10C H10B 109.1 . . ?
C9C C10C H10B 109.1 . . ?
C11C C10C H10A 109.1 . . ?
C9C C10C H10A 109.1 . . ?
H10B C10C H10A 107.9 . . ?
C11A C12A H12K 109.5 . . ?
C11A C12A H12J 109.5 . . ?
H12K C12A H12J 109.5 . . ?
C11A C12A H12L 109.5 . . ?
H12K C12A H12L 109.5 . . ?
H12J C12A H12L 109.5 . . ?
C11D C12D H12G 109.5 . . ?
C11D C12D H12I 109.5 . . ?
H12G C12D H12I 109.5 . . ?
C11D C12D H12H 109.5 . . ?
H12G C12D H12H 109.5 . . ?
H12I C12D H12H 109.5 . . ?
C10D C11D C12D 112.4(5) . . ?
C10D C11D H11F 109.1 . . ?
C12D C11D H11F 109.1 . . ?
C10D C11D H11E 109.1 . . ?
C12D C11D H11E 109.1 . . ?
H11F C11D H11E 107.9 . . ?
C10B C11B C12B 109.7(7) . . ?
C10B C11B H11D 109.7 . . ?
C12B C11B H11D 109.7 . . ?
C10B C11B H11C 109.7 . . ?
C12B C11B H11C 109.7 . . ?
H11D C11B H11C 108.2 . . ?
C11B C10B C9B 115.2(6) . . ?
C11B C10B H10D 108.5 . . ?
C9B C10B H10D 108.5 . . ?
C11B C10B H10C 108.5 . . ?
C9B C10B H10C 108.5 . . ?
H10D C10B H10C 107.5 . . ?

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
O2B S1B N1B C8B -40.2(5) . . . . ?
O1B S1B N1B C8B -169.6(4) . . . . ?
C5B S1B N1B C8B 76.3(5) . . . . ?
O3C C8C N1C S1C -15.0(8) . . . . ?
N2C C8C N1C S1C 165.5(4) . . . . ?
O2C S1C N1C C8C 49.3(5) . . . . ?
O1C S1C N1C C8C 177.7(5) . . . . ?
C5C S1C N1C C8C -68.8(5) . . . . ?
O3C C8C N2C C9C -8.2(9) . . . . ?
N1C C8C N2C C9C 171.3(5) . . . . ?
O2C S1C C5C C4C 21.3(6) . . . . ?
O1C S1C C5C C4C -109.5(5) . . . . ?
N1C S1C C5C C4C 140.4(5) . . . . ?
O2C S1C C5C C6C -164.5(5) . . . . ?
O1C S1C C5C C6C 64.7(5) . . . . ?
N1C S1C C5C C6C -45.3(5) . . . . ?
O3D C8D N2D C9D 6.8(8) . . . . ?
N1D C8D N2D C9D -172.4(5) . . . . ?
O3D C8D N1D S1D 0.9(8) . . . . ?
N2D C8D N1D S1D -179.8(4) . . . . ?
O2D S1D N1D C8D -33.3(5) . . . . ?
O1D S1D N1D C8D -162.6(4) . . . . ?
C5D S1D N1D C8D 83.5(5) . . . . ?
C9A N2A C8A O3A 1.0(8) . . . . ?
C9A N2A C8A N1A -178.5(5) . . . . ?
O2D S1D C5D C4D 34.3(5) . . . . ?
O1D S1D C5D C4D 166.5(5) . . . . ?
N1D S1D C5D C4D -82.7(5) . . . . ?
O2D S1D C5D C6D -146.9(5) . . . . ?
O1D S1D C5D C6D -14.7(5) . . . . ?
N1D S1D C5D C6D 96.1(5) . . . . ?
C8C N2C C9C C10C -84.2(6) . . . . ?
O1A S1A C5A C4A -113.5(5) . . . . ?
O2A S1A C5A C4A 18.0(5) . . . . ?
N1A S1A C5A C4A 136.1(5) . . . . ?
O1A S1A C5A C6A 61.9(5) . . . . ?
O2A S1A C5A C6A -166.6(5) . . . . ?
N1A S1A C5A C6A -48.5(5) . . . . ?
C9B N2B C8B O3B 12.4(9) . . . . ?
C9B N2B C8B N1B -167.8(5) . . . . ?
S1B N1B C8B O3B 2.9(8) . . . . ?
S1B N1B C8B N2B -176.8(4) . . . . ?
O3A C8A N1A S1A 9.0(7) . . . . ?
N2A C8A N1A S1A -171.5(4) . . . . ?
O1A S1A N1A C8A 172.6(4) . . . . ?
O2A S1A N1A C8A 43.0(5) . . . . ?
C5A S1A N1A C8A -72.9(5) . . . . ?
C8D N2D C9D C10D 74.4(6) . . . . ?
C6A C5A C4A C3A 0.7(9) . . . . ?
S1A C5A C4A C3A 176.1(4) . . . . ?
C4D C5D C6D C7D -0.8(9) . . . . ?
S1D C5D C6D C7D -179.6(5) . . . . ?
C6D C5D C4D C3D -0.1(9) . . . . ?
S1D C5D C4D C3D 178.7(5) . . . . ?
C8B N2B C9B C10B 89.2(7) . . . . ?
C2C C3C C4C C5C 0.3(9) . . . . ?
C6C C5C C4C C3C -1.5(9) . . . . ?
S1C C5C C4C C3C 172.8(5) . . . . ?
C4C C3C C2C C7C 0.8(9) . . . . ?
C4C C3C C2C C1C -179.0(6) . . . . ?
C6C C7C C2C C3C -0.9(10) . . . . ?
C6C C7C C2C C1C 179.0(6) . . . . ?
O2B S1B C5B C4B 29.9(5) . . . . ?
O1B S1B C5B C4B 161.1(4) . . . . ?
N1B S1B C5B C4B -87.9(5) . . . . ?
O2B S1B C5B C6B -150.6(5) . . . . ?
O1B S1B C5B C6B -19.3(5) . . . . ?
N1B S1B C5B C6B 91.7(5) . . . . ?
C8A N2A C9A C10A -104.5(6) . . . . ?
C4A C5A C6A C7A -1.7(9) . . . . ?
S1A C5A C6A C7A -177.0(5) . . . . ?
C5A C4A C3A C2A 0.3(9) . . . . ?
C2C C7C C6C C5C -0.3(10) . . . . ?
C4C C5C C6C C7C 1.4(9) . . . . ?
S1C C5C C6C C7C -172.8(5) . . . . ?
C4A C3A C2A C7A -0.4(9) . . . . ?
C4A C3A C2A C1A 177.1(6) . . . . ?
C6B C5B C4B C3B 1.0(9) . . . . ?
S1B C5B C4B C3B -179.4(5) . . . . ?
C5B C4B C3B C2B -1.0(9) . . . . ?
C4B C3B C2B C7B 0.2(9) . . . . ?
C4B C3B C2B C1B -179.9(6) . . . . ?
C3B C2B C7B C6B 0.5(9) . . . . ?
C1B C2B C7B C6B -179.4(6) . . . . ?
C3D C2D C7D C6D -0.5(10) . . . . ?
C1D C2D C7D C6D -178.7(6) . . . . ?
C5D C6D C7D C2D 1.1(9) . . . . ?
C2B C7B C6B C5B -0.4(9) . . . . ?
C4B C5B C6B C7B -0.3(9) . . . . ?
S1B C5B C6B C7B -179.9(5) . . . . ?
C5A C6A C7A C2A 1.7(9) . . . . ?
C3A C2A C7A C6A -0.6(9) . . . . ?
C1A C2A C7A C6A -178.1(6) . . . . ?
N2A C9A C10A C11A 61.6(7) . . . . ?
C5D C4D C3D C2D 0.7(9) . . . . ?
C7D C2D C3D C4D -0.4(10) . . . . ?
C1D C2D C3D C4D 177.8(6) . . . . ?
N2D C9D C10D C11D 63.2(7) . . . . ?
C9A C10A C11A C12A -177.6(6) . . . . ?
C12C C11C C10C C9C 178.1(7) . . . . ?
N2C C9C C10C C11C -71.4(7) . . . . ?
C9D C10D C11D C12D -177.2(5) . . . . ?
C12B C11B C10B C9B -177.2(7) . . . . ?
N2B C9B C10B C11B 174.0(6) . . . . ?

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
N1B H1B O3A 0.88 1.96 2.784(6) 155.4 .
N1C H1C O3D 0.88 1.94 2.707(5) 145.5 .
N2C H2C O3D 0.88 2.17 2.931(6) 145.0 .
N2C H2C O2D 0.88 2.33 3.043(5) 138.2 .
N2D H2D O2C 0.88 2.57 3.247(6) 133.9 1_455
N2D H2D O3C 0.88 2.24 2.982(6) 141.8 1_455
N2A H2A O2B 0.88 2.29 3.013(6) 138.8 2_554
N2A H2A O3B 0.88 2.31 3.065(6) 144.4 2_554
N2B H2B O3A 0.88 2.11 2.895(6) 147.5 .
N2B H2B O2A 0.88 2.46 3.109(6) 130.9 .
N1D H1D O3C 0.88 1.93 2.723(6) 148.4 1_455
N1A H1A O3B 0.88 1.92 2.735(6) 153.9 2_554
C4A H4A O1B 0.95 2.54 3.296(7) 136.5 1_655
C9B H9BB O1A 0.99 2.54 3.429(7) 149.8 2
C4C H4C O1D 0.95 2.45 3.165(7) 132.2 2_665
C9A H9AA O1A 0.99 2.45 3.270(6) 139.9 1_455

_refine_diff_density_max         0.457
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.063

_shelxl_version_number           2014/6

