# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1437552'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide
;
_chemical_name_common            chlorpropamide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 Cl N2 O3 S'
_chemical_formula_weight         276.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0050 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 0.0090 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0150 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1560 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1840 0.1585 '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                   6.1040(5)
_cell_length_b                   8.9243(8)
_cell_length_c                   12.0304(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.516(8)
_cell_angle_gamma                90
_cell_volume                     646.32(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    182
_cell_measurement_theta_min      3.2890
_cell_measurement_theta_max      21.5690

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.455
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.81984
_diffrn_radiation_type           x-rays
_diffrn_source                   synchrotron
_diffrn_measurement_device_type  
;
one-circle diffractometer
;
_diffrn_measurement_method       w\-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            715
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.980
_diffrn_reflns_theta_max         25.639
_diffrn_reflns_theta_full        25.639
_diffrn_measured_fraction_theta_max 0.619
_diffrn_measured_fraction_theta_full 0.619
_diffrn_reflns_Laue_measured_fraction_max 0.619
_diffrn_reflns_Laue_measured_fraction_full 0.619
_diffrn_reflns_point_group_measured_fraction_max 0.446
_diffrn_reflns_point_group_measured_fraction_full 0.446
_reflns_number_total             712
_reflns_number_gt                480
_reflns_threshold_expression     'I > 2σ(I)'


_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1121P)²+0.0453P] 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       .

_chemical_absolute_configuration unk
_refine_ls_number_reflns         712
_refine_ls_number_parameters     154
_refine_ls_number_restraints     143
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0665
_refine_ls_wR_factor_ref         0.2044
_refine_ls_wR_factor_gt          0.1878
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.071
_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 0.246(4) 0.416(3) 0.937(2) 0.093(8) Uani 1 1 d . U . . .
C2 C 0.367(4) 0.543(3) 0.937(2) 0.090(6) Uani 1 1 d . U . . .
H2 H 0.3480 0.6184 0.9876 0.108 Uiso 1 1 calc R U . . .
C3 C 0.515(4) 0.564(3) 0.8648(19) 0.089(6) Uani 1 1 d . U . . .
H3 H 0.5949 0.6528 0.8672 0.107 Uiso 1 1 calc R U . . .
C4 C 0.546(3) 0.452(3) 0.787(2) 0.079(6) Uani 1 1 d . U . . .
C5 C 0.427(4) 0.321(3) 0.792(2) 0.086(6) Uani 1 1 d . U . . .
H5 H 0.4488 0.2413 0.7456 0.103 Uiso 1 1 calc R U . . .
C6 C 0.279(4) 0.306(3) 0.865(2) 0.094(7) Uani 1 1 d . U . . .
H6 H 0.1986 0.2170 0.8652 0.113 Uiso 1 1 calc R U . . .
C7 C 0.430(3) 0.459(4) 0.502(2) 0.068(6) Uani 1 1 d . U . . .
C8 C 0.147(3) 0.476(3) 0.3406(17) 0.067(6) Uani 1 1 d . U . . .
H8A H 0.1923 0.3750 0.3242 0.081 Uiso 1 1 calc R U . . .
H8B H 0.1371 0.5341 0.2721 0.081 Uiso 1 1 calc R U . . .
C9 C -0.080(3) 0.468(4) 0.374(2) 0.105(8) Uani 1 1 d . U . . .
H9A H -0.0711 0.4113 0.4432 0.126 Uiso 1 1 calc R U . . .
H9B H -0.1289 0.5686 0.3879 0.126 Uiso 1 1 calc R U . . .
C10 C -0.247(3) 0.396(3) 0.284(2) 0.106(9) Uani 1 1 d . U . . .
H10A H -0.3887 0.3933 0.3083 0.159 Uiso 1 1 calc R U . . .
H10B H -0.2577 0.4530 0.2158 0.159 Uiso 1 1 calc R U . . .
H10C H -0.1999 0.2958 0.2710 0.159 Uiso 1 1 calc R U . . .
Cl1 Cl 0.0571(11) 0.3913(12) 1.0282(6) 0.129(3) Uani 1 1 d . U . . .
N1 N 0.577(3) 0.541(2) 0.5841(15) 0.079(5) Uani 1 1 d . U . . .
H1A H 0.5872 0.6356 0.5728 0.094 Uiso 1 1 calc R U . . .
N2 N 0.316(3) 0.5411(19) 0.4263(14) 0.066(5) Uani 1 1 d . U . . .
H2A H 0.3396 0.6360 0.4260 0.079 Uiso 1 1 calc R U . . .
O1 O 0.875(2) 0.5938(18) 0.7367(13) 0.089(5) Uani 1 1 d . U . . .
O2 O 0.816(2) 0.3306(19) 0.6761(14) 0.084(5) Uani 1 1 d . U . . .
O3 O 0.410(2) 0.321(2) 0.5201(13) 0.081(5) Uani 1 1 d . U . . .
S1 S 0.7306(9) 0.4735(7) 0.6975(6) 0.078(2) Uani 1 1 d . 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 C6 1.34(3) . ?
C1 C2 1.35(3) . ?
C1 Cl1 1.74(3) . ?
C2 C3 1.36(3) . ?
C3 C4 1.41(3) . ?
C4 C5 1.38(3) . ?
C4 S1 1.69(3) . ?
C5 C6 1.37(3) . ?
C7 O3 1.26(3) . ?
C7 N2 1.28(3) . ?
C7 N1 1.42(3) . ?
C8 N2 1.46(2) . ?
C8 C9 1.50(3) . ?
C9 C10 1.50(3) . ?
N1 S1 1.635(17) . ?
O1 S1 1.420(16) . ?
O2 S1 1.418(16) . ?

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
C6 C1 C2 119(3) . . ?
C6 C1 Cl1 120(2) . . ?
C2 C1 Cl1 122(2) . . ?
C1 C2 C3 122(3) . . ?
C2 C3 C4 120(3) . . ?
C5 C4 C3 116(3) . . ?
C5 C4 S1 123(2) . . ?
C3 C4 S1 121(2) . . ?
C6 C5 C4 122(3) . . ?
C1 C6 C5 121(3) . . ?
O3 C7 N2 128(2) . . ?
O3 C7 N1 117(2) . . ?
N2 C7 N1 114(3) . . ?
N2 C8 C9 113.9(17) . . ?
C10 C9 C8 112(2) . . ?
C7 N1 S1 126.7(18) . . ?
C7 N2 C8 121(2) . . ?
O2 S1 O1 120.8(8) . . ?
O2 S1 N1 110.9(10) . . ?
O1 S1 N1 103.7(10) . . ?
O2 S1 C4 108.4(13) . . ?
O1 S1 C4 108.7(11) . . ?
N1 S1 C4 102.9(10) . . ?

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
C6 C1 C2 C3 2(4) . . . . ?
Cl1 C1 C2 C3 -179.5(18) . . . . ?
C1 C2 C3 C4 0(3) . . . . ?
C2 C3 C4 C5 -3(3) . . . . ?
C2 C3 C4 S1 -179.2(18) . . . . ?
C3 C4 C5 C6 4(3) . . . . ?
S1 C4 C5 C6 180.0(17) . . . . ?
C2 C1 C6 C5 -1(4) . . . . ?
Cl1 C1 C6 C5 -179.7(18) . . . . ?
C4 C5 C6 C1 -2(3) . . . . ?
N2 C8 C9 C10 -178(2) . . . . ?
O3 C7 N1 S1 2(3) . . . . ?
N2 C7 N1 S1 174.5(16) . . . . ?
O3 C7 N2 C8 -5(4) . . . . ?
N1 C7 N2 C8 -176.0(16) . . . . ?
C9 C8 N2 C7 89(3) . . . . ?
C7 N1 S1 O2 38(2) . . . . ?
C7 N1 S1 O1 169.1(17) . . . . ?
C7 N1 S1 C4 -78(2) . . . . ?
C5 C4 S1 O2 -27(2) . . . . ?
C3 C4 S1 O2 148.6(18) . . . . ?
C5 C4 S1 O1 -160.5(18) . . . . ?
C3 C4 S1 O1 16(2) . . . . ?
C5 C4 S1 N1 90(2) . . . . ?
C3 C4 S1 N1 -93.9(18) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.049

