# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1833303'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-aminobenzenosulfonamid sulfamic acid salt'
_chemical_name_common            'sulfanilamid sulfamic acid salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H9 N2 O2 S, H2 N O3 S'
_chemical_formula_sum            'C6 H11 N3 O5 S2'
_chemical_formula_weight         269.30

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   4.81720(10)
_cell_length_b                   9.6864(3)
_cell_length_c                   11.2302(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.724(3)
_cell_angle_gamma                90
_cell_volume                     520.41(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4822
_cell_measurement_theta_min      3.6410
_cell_measurement_theta_max      31.2860

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.523
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            15834
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.654
_diffrn_reflns_theta_max         31.805
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3370
_reflns_number_gt                3014
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_max     0.925
_reflns_Friedel_fraction_full    0.999

_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 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_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)+(0.0347P)²+0.3181P] 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 1277 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3370
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
S2 S 0.14043(14) 1.42372(7) 0.64194(6) 0.01141(15) Uani 1 1 d . . . . .
S1 S 0.71819(15) 1.14636(8) 0.94296(7) 0.01297(16) Uani 1 1 d . . . . .
O2 O 1.0188(4) 1.1493(3) 0.9697(2) 0.0195(5) Uani 1 1 d . . . . .
O21 O 0.0587(5) 1.2992(2) 0.5712(2) 0.0166(5) Uani 1 1 d . . . . .
O1 O 0.5776(5) 1.2701(2) 0.8981(2) 0.0171(5) Uani 1 1 d . . . . .
O22 O -0.0034(5) 1.5465(2) 0.5934(2) 0.0153(5) Uani 1 1 d . . . . .
O23 O 0.4429(4) 1.4402(3) 0.6595(2) 0.0185(5) Uani 1 1 d . . . . .
N1 N 0.5958(6) 1.1036(3) 1.0640(3) 0.0175(6) Uani 1 1 d . . . . .
H11 H 0.423(10) 1.093(4) 1.061(4) 0.021 Uiso 1 1 d . U . . .
H12 H 0.684(9) 1.037(5) 1.100(4) 0.021 Uiso 1 1 d . U . . .
N2 N 0.0467(6) 1.4055(3) 0.7775(2) 0.0146(5) Uani 1 1 d . . . . .
H21 H -0.123(9) 1.400(4) 0.773(4) 0.018 Uiso 1 1 d . U . . .
H22 H 0.135(8) 1.338(4) 0.812(4) 0.018 Uiso 1 1 d . U . . .
N4 N 0.4990(6) 0.7193(3) 0.5590(3) 0.0138(5) Uani 1 1 d . . . . .
H41 H 0.318(9) 0.732(4) 0.517(4) 0.017 Uiso 1 1 d . U . . .
H42 H 0.495(8) 0.634(5) 0.581(3) 0.017 Uiso 1 1 d . U . . .
H43 H 0.624(9) 0.725(4) 0.522(4) 0.017 Uiso 1 1 d . U . . .
C1 C 0.6450(6) 1.0175(3) 0.8322(3) 0.0128(5) Uani 1 1 d . . . . .
C6 C 0.8048(7) 0.8983(3) 0.8380(3) 0.0189(7) Uani 1 1 d . . . . .
H6 H 0.947194 0.884625 0.902914 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5459(6) 0.8213(3) 0.6562(3) 0.0136(6) Uani 1 1 d . . . . .
C5 C 0.7567(7) 0.7988(3) 0.7490(3) 0.0185(6) Uani 1 1 d . . . . .
H5 H 0.866125 0.717077 0.751742 0.028 Uiso 1 1 calc R U . . .
C2 C 0.4331(7) 1.0383(4) 0.7392(3) 0.0201(7) Uani 1 1 d . . . . .
H2 H 0.322736 1.119705 0.736760 0.030 Uiso 1 1 calc R U . . .
C3 C 0.3830(7) 0.9392(4) 0.6497(3) 0.0197(7) Uani 1 1 d . . . . .
H3 H 0.239328 0.952335 0.585219 0.030 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
S2 O22 1.450(2) . ?
S2 O23 1.456(2) . ?
S2 O21 1.473(2) . ?
S2 N2 1.647(3) . ?
S1 O1 1.439(2) . ?
S1 O2 1.444(2) . ?
S1 N1 1.598(3) . ?
S1 C1 1.768(3) . ?
N1 H11 0.83(5) . ?
N1 H12 0.85(5) . ?
N2 H21 0.82(4) . ?
N2 H22 0.85(4) . ?
N4 C4 1.470(4) . ?
N4 H41 0.95(4) . ?
N4 H42 0.86(5) . ?
N4 H43 0.77(4) . ?
C1 C6 1.385(4) . ?
C1 C2 1.387(4) . ?
C6 C5 1.388(5) . ?
C6 H6 0.9500 . ?
C4 C3 1.383(5) . ?
C4 C5 1.385(5) . ?
C5 H5 0.9500 . ?
C2 C3 1.390(5) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?

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
O22 S2 O23 112.80(14) . . ?
O22 S2 O21 112.54(13) . . ?
O23 S2 O21 111.27(15) . . ?
O22 S2 N2 105.35(14) . . ?
O23 S2 N2 105.36(14) . . ?
O21 S2 N2 109.02(14) . . ?
O1 S1 O2 118.42(16) . . ?
O1 S1 N1 107.94(15) . . ?
O2 S1 N1 106.81(15) . . ?
O1 S1 C1 107.16(15) . . ?
O2 S1 C1 105.80(14) . . ?
N1 S1 C1 110.64(15) . . ?
S1 N1 H11 118(3) . . ?
S1 N1 H12 113(3) . . ?
H11 N1 H12 111(4) . . ?
S2 N2 H21 110(3) . . ?
S2 N2 H22 109(3) . . ?
H21 N2 H22 115(4) . . ?
C4 N4 H41 110(2) . . ?
C4 N4 H42 116(3) . . ?
H41 N4 H42 103(4) . . ?
C4 N4 H43 107(3) . . ?
H41 N4 H43 117(4) . . ?
H42 N4 H43 105(4) . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 S1 119.4(2) . . ?
C2 C1 S1 119.7(2) . . ?
C1 C6 C5 120.0(3) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C3 C4 C5 122.0(3) . . ?
C3 C4 N4 118.6(3) . . ?
C5 C4 N4 119.3(3) . . ?
C4 C5 C6 118.6(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C1 C2 C3 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?

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
O1 S1 C1 C6 164.7(3) . . . . ?
O2 S1 C1 C6 37.4(3) . . . . ?
N1 S1 C1 C6 -77.9(3) . . . . ?
O1 S1 C1 C2 -13.9(3) . . . . ?
O2 S1 C1 C2 -141.1(3) . . . . ?
N1 S1 C1 C2 103.6(3) . . . . ?
C2 C1 C6 C5 1.1(5) . . . . ?
S1 C1 C6 C5 -177.4(3) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
N4 C4 C5 C6 177.8(3) . . . . ?
C1 C6 C5 C4 -0.6(5) . . . . ?
C6 C1 C2 C3 -1.0(5) . . . . ?
S1 C1 C2 C3 177.5(3) . . . . ?
C5 C4 C3 C2 0.1(5) . . . . ?
N4 C4 C3 C2 -177.8(3) . . . . ?
C1 C2 C3 C4 0.4(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
_geom_hbond_publ_flag
N1 H11 O2 0.83(5) 2.16(4) 2.890(4) 146(4) 1_455 yes
N1 H12 N2 0.85(5) 2.18(5) 3.017(4) 166(4) 2_647 yes
N2 H21 O1 0.82(4) 2.47(4) 3.062(4) 131(4) 1_455 yes
N2 H21 O23 0.82(4) 2.35(4) 3.070(3) 147(4) 1_455 yes
N2 H22 O1 0.85(4) 2.33(4) 3.047(4) 142(3) . yes
N4 H41 O21 0.95(4) 2.07(4) 3.006(4) 169(4) 2_546 yes
N4 H42 O23 0.86(5) 2.10(5) 2.954(4) 170(4) 1_545 yes
N4 H43 O21 0.77(4) 2.08(4) 2.830(4) 164(4) 2_646 yes
C5 H5 O22 0.95 2.56 3.292(4) 134.1 1_645 yes
C3 H3 O21 0.95 2.60 3.360(4) 137.3 2_546 yes
C3 H3 O22 0.95 2.37 3.273(4) 158.7 2_546 yes

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1833304'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'4-aminobenzenesulfonamide (4-sulfamoyl-phenyl)oxalamic acid salt'
_chemical_name_common            
'sulfanilamide (4-sulfamoyl-phenyl)oxalamic acid salt'
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 N2 O5 S, C6 H9 N2 O2 S'
_chemical_formula_sum            'C14 H16 N4 O7 S2'
_chemical_formula_weight         416.43

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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                   17.2685(4)
_cell_length_b                   6.2883(2)
_cell_length_c                   7.9171(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.627(3)
_cell_angle_gamma                90
_cell_volume                     852.11(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    12463
_cell_measurement_theta_min      3.5610
_cell_measurement_theta_max      27.2550

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_reflns_number            3347
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.452
_diffrn_reflns_theta_max         29.684
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.756
_diffrn_reflns_point_group_measured_fraction_full 0.775
_reflns_number_total             3347
_reflns_number_gt                2472
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.547
_reflns_Friedel_fraction_max     0.536
_reflns_Friedel_fraction_full    0.553

_reflns_special_details          
;
 _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 1.171.38.41r (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41r (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae, 2008)'
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)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 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.22(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3347
_refine_ls_number_parameters     269
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.965
_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
S1B S 0.71910(5) 0.27406(15) 0.79592(9) 0.0303(2) Uani 1 1 d . . . . .
S1A S -0.06672(6) 0.24528(16) 0.11233(12) 0.0323(3) Uani 1 1 d . . . . .
O1A O -0.0578(2) 0.4500(6) 0.0420(5) 0.0589(10) Uani 1 1 d . . . . .
N4A N 0.2348(2) -0.0029(5) 0.5115(5) 0.0342(8) Uani 1 1 d D . . . .
H4A H 0.238(3) -0.135(4) 0.520(6) 0.041 Uiso 1 1 d D U . . .
O7A O 0.29252(18) 0.3067(4) 0.6155(4) 0.0468(7) Uani 1 1 d . . . . .
O2A O -0.0932(2) 0.0720(6) 0.0035(4) 0.0514(9) Uani 1 1 d . . . . .
O8A2 O 0.34514(17) -0.2242(4) 0.6899(4) 0.0379(6) Uani 1 1 d . . . . .
N2B N 0.7773(3) 0.2249(6) 0.6614(5) 0.0365(9) Uani 1 1 d D . . . .
H2B1 H 0.760(3) 0.133(6) 0.587(5) 0.044 Uiso 1 1 d D U . . .
H2B2 H 0.785(3) 0.339(5) 0.606(5) 0.044 Uiso 1 1 d D U . . .
C4A C 0.1652(2) 0.0645(6) 0.4123(5) 0.0296(8) Uani 1 1 d . . . . .
O8A1 O 0.40307(18) 0.0680(4) 0.8063(4) 0.0511(8) Uani 1 1 d . . . . .
O2B O 0.75046(19) 0.4488(5) 0.8967(4) 0.0444(8) Uani 1 1 d . . . . .
N4B N 0.4085(2) 0.5270(6) 0.4260(5) 0.0320(7) Uani 1 1 d D . . . .
H4B1 H 0.391(3) 0.429(6) 0.352(4) 0.038 Uiso 1 1 d D U . . .
H4B2 H 0.405(3) 0.648(8) 0.366(6) 0.038 Uiso 1 1 d . U . . .
H4B3 H 0.376(3) 0.525(7) 0.508(6) 0.038 Uiso 1 1 d . U . . .
O1B O 0.7043(2) 0.0776(5) 0.8762(5) 0.0511(8) Uani 1 1 d . . . . .
N1A N -0.1268(3) 0.2690(7) 0.2481(6) 0.0426(10) Uani 1 1 d D . . . .
H1A1 H -0.117(3) 0.375(9) 0.301(6) 0.051 Uiso 1 1 d . U . . .
H1A2 H -0.138(3) 0.145(4) 0.287(6) 0.051 Uiso 1 1 d D U . . .
C2A C 0.0753(3) 0.3257(8) 0.2921(8) 0.0628(16) Uani 1 1 d . . . . .
H2A H 0.0619 0.4681 0.2754 0.094 Uiso 1 1 calc R U . . .
C1A C 0.0249(2) 0.1721(6) 0.2228(5) 0.0318(9) Uani 1 1 d . . . . .
C6B C 0.6073(3) 0.5685(7) 0.6742(6) 0.0438(11) Uani 1 1 d . . . . .
H6B H 0.6413 0.6726 0.7239 0.066 Uiso 1 1 calc R U . . .
C5A C 0.1147(3) -0.0904(6) 0.3405(6) 0.0393(10) Uani 1 1 d . . . . .
H5A H 0.1283 -0.2328 0.3564 0.059 Uiso 1 1 calc R U . . .
C5B C 0.5346(3) 0.6244(6) 0.5887(6) 0.0438(11) Uani 1 1 d . . . . .
H5B H 0.5194 0.7663 0.5821 0.066 Uiso 1 1 calc R U . . .
C7A C 0.2896(2) 0.1141(6) 0.6074(5) 0.0297(7) Uani 1 1 d . . . . .
C1B C 0.6284(2) 0.3584(6) 0.6845(5) 0.0283(8) Uani 1 1 d . . . . .
C8A C 0.3521(2) -0.0265(5) 0.7109(5) 0.0315(7) Uani 1 1 d . . . . .
C3A C 0.1463(3) 0.2726(7) 0.3875(9) 0.0571(18) Uani 1 1 d . . . . .
H3A H 0.1803 0.3785 0.4336 0.086 Uiso 1 1 calc R U . . .
C4B C 0.4860(2) 0.4719(6) 0.5150(5) 0.0272(8) Uani 1 1 d . . . . .
C6A C 0.0445(3) -0.0383(7) 0.2457(6) 0.0379(10) Uani 1 1 d . . . . .
H6A H 0.0109 -0.1443 0.1979 0.057 Uiso 1 1 calc R U . . .
C3B C 0.5078(4) 0.2636(8) 0.5246(9) 0.0616(19) Uani 1 1 d . . . . .
H3B H 0.4740 0.1602 0.4732 0.092 Uiso 1 1 calc R U . . .
C2B C 0.5786(4) 0.2052(8) 0.6090(8) 0.0631(17) Uani 1 1 d . . . . .
H2B H 0.5930 0.0627 0.6154 0.095 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
S1B O2B 1.422(3) . ?
S1B O1B 1.428(3) . ?
S1B N2B 1.589(4) . ?
S1B C1B 1.774(4) . ?
S1A O1A 1.419(4) . ?
S1A O2A 1.426(3) . ?
S1A N1A 1.597(5) . ?
S1A C1A 1.764(4) . ?
N4A C7A 1.350(5) . ?
N4A C4A 1.410(5) . ?
N4A H4A 0.84(2) . ?
O7A C7A 1.213(4) . ?
O8A2 C8A 1.258(4) . ?
N2B H2B1 0.85(2) . ?
N2B H2B2 0.86(2) . ?
C4A C3A 1.357(6) . ?
C4A C5A 1.379(6) . ?
O8A1 C8A 1.234(4) . ?
N4B C4B 1.470(5) . ?
N4B H4B1 0.87(2) . ?
N4B H4B2 0.90(5) . ?
N4B H4B3 0.91(5) . ?
N1A H1A1 0.79(5) . ?
N1A H1A2 0.871(17) . ?
C2A C1A 1.365(6) . ?
C2A C3A 1.393(8) . ?
C2A H2A 0.9300 . ?
C1A C6A 1.372(6) . ?
C6B C1B 1.370(6) . ?
C6B C5B 1.390(6) . ?
C6B H6B 0.9300 . ?
C5A C6A 1.378(6) . ?
C5A H5A 0.9300 . ?
C5B C4B 1.355(6) . ?
C5B H5B 0.9300 . ?
C7A C8A 1.544(5) . ?
C1B C2B 1.375(7) . ?
C3A H3A 0.9300 . ?
C4B C3B 1.362(6) . ?
C6A H6A 0.9300 . ?
C3B C2B 1.363(8) . ?
C3B H3B 0.9300 . ?
C2B H2B 0.9300 . ?

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
O2B S1B O1B 119.8(2) . . ?
O2B S1B N2B 107.4(2) . . ?
O1B S1B N2B 107.3(2) . . ?
O2B S1B C1B 107.1(2) . . ?
O1B S1B C1B 106.4(2) . . ?
N2B S1B C1B 108.64(19) . . ?
O1A S1A O2A 119.9(2) . . ?
O1A S1A N1A 107.1(2) . . ?
O2A S1A N1A 107.0(2) . . ?
O1A S1A C1A 107.1(2) . . ?
O2A S1A C1A 107.2(2) . . ?
N1A S1A C1A 108.1(2) . . ?
C7A N4A C4A 129.1(3) . . ?
C7A N4A H4A 118(3) . . ?
C4A N4A H4A 113(3) . . ?
S1B N2B H2B1 114(3) . . ?
S1B N2B H2B2 109(3) . . ?
H2B1 N2B H2B2 106(4) . . ?
C3A C4A C5A 119.6(4) . . ?
C3A C4A N4A 122.8(4) . . ?
C5A C4A N4A 117.6(4) . . ?
C4B N4B H4B1 111(3) . . ?
C4B N4B H4B2 116(3) . . ?
H4B1 N4B H4B2 105(4) . . ?
C4B N4B H4B3 105(3) . . ?
H4B1 N4B H4B3 106(4) . . ?
H4B2 N4B H4B3 113(4) . . ?
S1A N1A H1A1 109(4) . . ?
S1A N1A H1A2 111(3) . . ?
H1A1 N1A H1A2 127(5) . . ?
C1A C2A C3A 121.1(4) . . ?
C1A C2A H2A 119.4 . . ?
C3A C2A H2A 119.4 . . ?
C2A C1A C6A 119.8(4) . . ?
C2A C1A S1A 119.8(3) . . ?
C6A C1A S1A 120.4(3) . . ?
C1B C6B C5B 119.2(4) . . ?
C1B C6B H6B 120.4 . . ?
C5B C6B H6B 120.4 . . ?
C6A C5A C4A 121.3(4) . . ?
C6A C5A H5A 119.4 . . ?
C4A C5A H5A 119.4 . . ?
C4B C5B C6B 119.9(4) . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
O7A C7A N4A 126.5(3) . . ?
O7A C7A C8A 121.5(3) . . ?
N4A C7A C8A 112.0(3) . . ?
C6B C1B C2B 120.3(4) . . ?
C6B C1B S1B 121.9(3) . . ?
C2B C1B S1B 117.8(3) . . ?
O8A1 C8A O8A2 127.2(3) . . ?
O8A1 C8A C7A 116.2(3) . . ?
O8A2 C8A C7A 116.6(3) . . ?
C4A C3A C2A 119.2(4) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C5B C4B C3B 120.4(4) . . ?
C5B C4B N4B 120.8(3) . . ?
C3B C4B N4B 118.7(4) . . ?
C1A C6A C5A 119.0(4) . . ?
C1A C6A H6A 120.5 . . ?
C5A C6A H6A 120.5 . . ?
C4B C3B C2B 120.6(5) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C3B C2B C1B 119.5(5) . . ?
C3B C2B H2B 120.2 . . ?
C1B C2B H2B 120.2 . . ?

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
C7A N4A C4A C3A 6.0(8) . . . . ?
C7A N4A C4A C5A -173.1(4) . . . . ?
C3A C2A C1A C6A -0.6(9) . . . . ?
C3A C2A C1A S1A 176.7(5) . . . . ?
O1A S1A C1A C2A 28.9(5) . . . . ?
O2A S1A C1A C2A 158.8(4) . . . . ?
N1A S1A C1A C2A -86.2(5) . . . . ?
O1A S1A C1A C6A -153.9(4) . . . . ?
O2A S1A C1A C6A -24.0(4) . . . . ?
N1A S1A C1A C6A 91.0(4) . . . . ?
C3A C4A C5A C6A -1.0(8) . . . . ?
N4A C4A C5A C6A 178.2(4) . . . . ?
C1B C6B C5B C4B -0.8(8) . . . . ?
C4A N4A C7A O7A -6.6(7) . . . . ?
C4A N4A C7A C8A 173.8(4) . . . . ?
C5B C6B C1B C2B 0.9(8) . . . . ?
C5B C6B C1B S1B -178.4(3) . . . . ?
O2B S1B C1B C6B 13.8(4) . . . . ?
O1B S1B C1B C6B 142.9(4) . . . . ?
N2B S1B C1B C6B -101.9(4) . . . . ?
O2B S1B C1B C2B -165.5(4) . . . . ?
O1B S1B C1B C2B -36.3(5) . . . . ?
N2B S1B C1B C2B 78.9(5) . . . . ?
O7A C7A C8A O8A1 2.6(5) . . . . ?
N4A C7A C8A O8A1 -177.8(4) . . . . ?
O7A C7A C8A O8A2 -177.9(4) . . . . ?
N4A C7A C8A O8A2 1.7(5) . . . . ?
C5A C4A C3A C2A 1.1(9) . . . . ?
N4A C4A C3A C2A -178.0(5) . . . . ?
C1A C2A C3A C4A -0.4(10) . . . . ?
C6B C5B C4B C3B 0.2(8) . . . . ?
C6B C5B C4B N4B 179.2(4) . . . . ?
C2A C1A C6A C5A 0.8(7) . . . . ?
S1A C1A C6A C5A -176.5(4) . . . . ?
C4A C5A C6A C1A 0.0(7) . . . . ?
C5B C4B C3B C2B 0.3(10) . . . . ?
N4B C4B C3B C2B -178.7(6) . . . . ?
C4B C3B C2B C1B -0.2(11) . . . . ?
C6B C1B C2B C3B -0.4(9) . . . . ?
S1B C1B C2B C3B 178.9(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
N2B H2B1 O1B 0.85(2) 2.24(2) 3.090(5) 173(4) 2_554
N2B H2B2 O2B 0.86(2) 2.15(3) 2.925(5) 150(4) 2_564
N4B H4B1 O8A2 0.87(2) 1.92(2) 2.788(4) 175(4) 2_554
N4B H4B2 O8A1 0.90(5) 1.84(5) 2.715(5) 163(4) 2_564
N4B H4B3 O7A 0.91(5) 2.24(5) 2.996(5) 140(4) .
N4B H4B3 O8A2 0.91(5) 2.25(5) 2.935(5) 132(4) 1_565
N1A H1A1 O1A 0.79(5) 2.32(5) 3.036(6) 151(5) 2_565
N1A H1A2 O2A 0.871(17) 2.25(4) 2.951(5) 138(4) 2
C3A H3A O7A 0.93 2.30 2.911(6) 122.7 .
C3B H3B O8A1 0.93 2.21 3.126(6) 169.1 2_554

_refine_diff_density_max         0.208
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.054

