# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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 1574767'
_audit_update_record             
;
2017-09-15 deposited with the CCDC.
2018-01-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
chalcone2,5-dichloro-N-{3-[(2E)-3-(4-nitrophenyl)prop-2-enoyl]phenyl}benzenesulfonamide
_chemical_name_common            'sulfonamide chalcone'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Cl2 N2 O5 S'
_chemical_formula_weight         477.30

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'
Cl Cl 0.1484 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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   22.2982(18)
_cell_length_b                   8.5917(8)
_cell_length_c                   26.0739(14)
_cell_angle_alpha                90
_cell_angle_beta                 112.116(5)
_cell_angle_gamma                90
_cell_volume                     4627.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    11945

_cell_measurement_theta_min      1.686
_cell_measurement_theta_max      26.528

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale yellow'

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10

_exptl_absorpt_coefficient_mu    0.405
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26695
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.686
_diffrn_reflns_theta_max         26.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4793
_reflns_number_gt                3115
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0716P)²+6.4787P] 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_number_reflns         4793
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1490
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.34505(4) 0.40629(9) 0.38813(3) 0.0484(2) Uani 1 1 d . . . . .
Cl2 Cl 0.43352(6) 0.27939(17) 0.32228(6) 0.1087(5) Uani 1 1 d . . . . .
Cl1 Cl 0.13891(8) 0.3548(2) 0.19667(8) 0.1792(10) Uani 1 1 d . . . . .
O3 O 0.47954(11) -0.2285(3) 0.52105(11) 0.0682(7) Uani 1 1 d . . . . .
N2 N 0.38207(13) 0.2555(3) 0.42246(11) 0.0526(7) Uani 1 1 d . . . . .
O5 O 0.39383(10) 0.5210(2) 0.39600(9) 0.0612(6) Uani 1 1 d . . . . .
O4 O 0.29087(11) 0.4420(3) 0.40250(10) 0.0619(6) Uani 1 1 d . . . . .
C4 C 0.42461(14) -0.6679(3) 0.56481(13) 0.0482(7) Uani 1 1 d . . . . .
C15 C 0.39604(14) -0.0004(3) 0.46102(12) 0.0442(7) Uani 1 1 d . . . . .
H15 H 0.440439 0.016578 0.473425 0.053 Uiso 1 1 calc R U . . .
C8 C 0.40000(15) -0.4047(3) 0.52228(13) 0.0499(7) Uani 1 1 d . . . . .
H8 H 0.356009 -0.419454 0.513901 0.060 Uiso 1 1 calc R U . . .
C9 C 0.42195(15) -0.2569(3) 0.50644(12) 0.0472(7) Uani 1 1 d . . . . .
C11 C 0.30660(15) -0.1654(3) 0.45345(13) 0.0521(8) Uani 1 1 d . . . . .
H11 H 0.290380 -0.258618 0.461036 0.062 Uiso 1 1 calc R U . . .
C14 C 0.35378(14) 0.1150(3) 0.43114(12) 0.0451(7) Uani 1 1 d . . . . .
N1 N 0.38481(17) -1.1043(4) 0.61907(15) 0.0663(8) Uani 1 1 d . . . . .
C10 C 0.37299(14) -0.1408(3) 0.47267(12) 0.0430(7) Uani 1 1 d . . . . .
C1 C 0.39896(15) -0.9532(3) 0.59999(13) 0.0514(8) Uani 1 1 d . . . . .
C7 C 0.44035(16) -0.5154(4) 0.54768(14) 0.0540(8) Uani 1 1 d . . . . .
C13 C 0.28748(15) 0.0886(4) 0.41203(14) 0.0544(8) Uani 1 1 d . . . . .
H13 H 0.258591 0.164876 0.391898 0.065 Uiso 1 1 calc R U . . .
C5 C 0.47412(16) -0.7702(4) 0.59255(14) 0.0585(9) Uani 1 1 d . . . . .
H5 H 0.516674 -0.741058 0.599657 0.070 Uiso 1 1 calc R U . . .
C3 C 0.36103(15) -0.7152(4) 0.55390(14) 0.0549(8) Uani 1 1 d . . . . .
H3 H 0.326960 -0.649364 0.534352 0.066 Uiso 1 1 calc R U . . .
O1 O 0.3292(14) -1.125(5) 0.620(2) 0.108(9) Uani 0.40(7) 1 d . . P A 1
O2 O 0.4334(15) -1.164(5) 0.657(2) 0.132(11) Uani 0.40(7) 1 d . . P A 1
O1' O 0.3317(9) -1.1527(18) 0.5990(11) 0.088(5) Uani 0.60(7) 1 d . . P A 2
O2' O 0.4253(8) -1.1942(19) 0.6410(11) 0.097(5) Uani 0.60(7) 1 d . . P A 2
C6 C 0.46203(16) -0.9141(4) 0.60994(15) 0.0609(9) Uani 1 1 d . . . . .
H6 H 0.495657 -0.982706 0.627901 0.073 Uiso 1 1 calc R U . . .
C2 C 0.34803(15) -0.8572(4) 0.57160(14) 0.0565(8) Uani 1 1 d . . . . .
H2 H 0.305630 -0.887697 0.564501 0.068 Uiso 1 1 calc R U . . .
C16 C 0.31257(16) 0.3519(3) 0.31730(13) 0.0540(8) Uani 1 1 d . . . . .
C17 C 0.24673(17) 0.3662(4) 0.28912(15) 0.0694(10) Uani 1 1 d . . . . .
H17 H 0.220178 0.399005 0.307270 0.083 Uiso 1 1 calc R U . . .
C12 C 0.26493(15) -0.0517(4) 0.42321(15) 0.0581(9) Uani 1 1 d . . . . .
H12 H 0.220563 -0.069783 0.409991 0.070 Uiso 1 1 calc R U . . .
C21 C 0.3513(2) 0.2995(5) 0.28942(17) 0.0770(11) Uani 1 1 d . . . . .
C20 C 0.3235(3) 0.2626(6) 0.2342(2) 0.1086(17) Uani 1 1 d . . . . .
H20 H 0.349486 0.227724 0.215809 0.130 Uiso 1 1 calc R U . . .
C19 C 0.2590(4) 0.2764(6) 0.2062(2) 0.116(2) Uani 1 1 d . . . . .
H19 H 0.240806 0.248938 0.169039 0.140 Uiso 1 1 calc R U . . .
C18 C 0.2204(2) 0.3300(5) 0.2322(2) 0.0969(16) Uani 1 1 d . . . . .
H7 H 0.484(2) -0.507(6) 0.5550(19) 0.116 Uiso 1 1 d . U . . .
HN1 H 0.422(2) 0.262(6) 0.431(2) 0.116 Uiso 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
S1 O5 1.424(2) . ?
S1 O4 1.427(2) . ?
S1 N2 1.614(3) . ?
S1 C16 1.774(3) . ?
Cl2 C21 1.714(4) . ?
Cl1 C18 1.715(5) . ?
O3 C9 1.219(3) . ?
N2 C14 1.419(4) . ?
N2 HN1 0.84(5) . ?
C4 C5 1.383(4) . ?
C4 C3 1.397(4) . ?
C4 C7 1.469(4) . ?
C15 C14 1.387(4) . ?
C15 C10 1.390(4) . ?
C15 H15 0.9300 . ?
C8 C7 1.306(4) . ?
C8 C9 1.474(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.496(4) . ?
C11 C12 1.374(4) . ?
C11 C10 1.389(4) . ?
C11 H11 0.9300 . ?
C14 C13 1.389(4) . ?
N1 O2' 1.162(14) . ?
N1 O1' 1.175(16) . ?
N1 O1 1.26(2) . ?
N1 O2 1.27(3) . ?
N1 C1 1.467(4) . ?
C1 C6 1.372(4) . ?
C1 C2 1.373(4) . ?
C7 H7 0.93(4) . ?
C13 C12 1.379(4) . ?
C13 H13 0.9300 . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C3 C2 1.374(4) . ?
C3 H3 0.9300 . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C16 C17 1.378(5) . ?
C16 C21 1.397(5) . ?
C17 C18 1.409(6) . ?
C17 H17 0.9300 . ?
C12 H12 0.9300 . ?
C21 C20 1.372(6) . ?
C20 C19 1.352(8) . ?
C20 H20 0.9300 . ?
C19 C18 1.359(8) . ?
C19 H19 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
O5 S1 O4 119.31(14) . . ?
O5 S1 N2 105.79(13) . . ?
O4 S1 N2 109.52(14) . . ?
O5 S1 C16 108.83(15) . . ?
O4 S1 C16 106.01(15) . . ?
N2 S1 C16 106.80(15) . . ?
C14 N2 S1 127.3(2) . . ?
C14 N2 HN1 120(3) . . ?
S1 N2 HN1 112(3) . . ?
C5 C4 C3 118.1(3) . . ?
C5 C4 C7 119.4(3) . . ?
C3 C4 C7 122.5(3) . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C7 C8 C9 122.1(3) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
O3 C9 C8 120.4(3) . . ?
O3 C9 C10 120.0(3) . . ?
C8 C9 C10 119.6(3) . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 N2 116.7(3) . . ?
C13 C14 N2 123.9(3) . . ?
O2' N1 O1' 116.8(14) . . ?
O1 N1 O2 119(2) . . ?
O2' N1 C1 121.9(8) . . ?
O1' N1 C1 118.1(9) . . ?
O1 N1 C1 118.0(14) . . ?
O2 N1 C1 113.0(16) . . ?
C11 C10 C15 119.0(3) . . ?
C11 C10 C9 123.6(3) . . ?
C15 C10 C9 117.4(3) . . ?
C6 C1 C2 122.4(3) . . ?
C6 C1 N1 119.3(3) . . ?
C2 C1 N1 118.3(3) . . ?
C8 C7 C4 127.3(3) . . ?
C8 C7 H7 121(3) . . ?
C4 C7 H7 111(3) . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C17 C16 C21 119.7(3) . . ?
C17 C16 S1 117.9(3) . . ?
C21 C16 S1 122.4(3) . . ?
C16 C17 C18 118.6(4) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C20 C21 C16 119.7(4) . . ?
C20 C21 Cl2 118.5(4) . . ?
C16 C21 Cl2 121.8(3) . . ?
C19 C20 C21 121.0(5) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C19 C18 120.3(5) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C18 C17 120.6(5) . . ?
C19 C18 Cl1 120.8(5) . . ?
C17 C18 Cl1 118.6(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
O5 S1 N2 C14 174.5(3) . . . . ?
O4 S1 N2 C14 44.8(3) . . . . ?
C16 S1 N2 C14 -69.6(3) . . . . ?
C7 C8 C9 O3 -6.4(5) . . . . ?
C7 C8 C9 C10 174.2(3) . . . . ?
C10 C15 C14 C13 -0.8(5) . . . . ?
C10 C15 C14 N2 178.6(3) . . . . ?
S1 N2 C14 C15 178.3(2) . . . . ?
S1 N2 C14 C13 -2.3(5) . . . . ?
C12 C11 C10 C15 0.3(5) . . . . ?
C12 C11 C10 C9 179.2(3) . . . . ?
C14 C15 C10 C11 0.6(4) . . . . ?
C14 C15 C10 C9 -178.4(3) . . . . ?
O3 C9 C10 C11 178.7(3) . . . . ?
C8 C9 C10 C11 -1.9(4) . . . . ?
O3 C9 C10 C15 -2.4(4) . . . . ?
C8 C9 C10 C15 177.0(3) . . . . ?
O2' N1 C1 C6 -2.4(16) . . . . ?
O1' N1 C1 C6 -161.3(17) . . . . ?
O1 N1 C1 C6 166(3) . . . . ?
O2 N1 C1 C6 20(3) . . . . ?
O2' N1 C1 C2 176.2(16) . . . . ?
O1' N1 C1 C2 17.3(17) . . . . ?
O1 N1 C1 C2 -15(3) . . . . ?
O2 N1 C1 C2 -161(3) . . . . ?
C9 C8 C7 C4 -179.0(3) . . . . ?
C5 C4 C7 C8 -178.6(4) . . . . ?
C3 C4 C7 C8 1.8(6) . . . . ?
C15 C14 C13 C12 0.1(5) . . . . ?
N2 C14 C13 C12 -179.3(3) . . . . ?
C3 C4 C5 C6 -0.9(5) . . . . ?
C7 C4 C5 C6 179.4(3) . . . . ?
C5 C4 C3 C2 1.9(5) . . . . ?
C7 C4 C3 C2 -178.5(3) . . . . ?
C2 C1 C6 C5 2.7(5) . . . . ?
N1 C1 C6 C5 -178.7(3) . . . . ?
C4 C5 C6 C1 -1.3(6) . . . . ?
C6 C1 C2 C3 -1.8(5) . . . . ?
N1 C1 C2 C3 179.6(3) . . . . ?
C4 C3 C2 C1 -0.6(5) . . . . ?
O5 S1 C16 C17 -123.9(3) . . . . ?
O4 S1 C16 C17 5.6(3) . . . . ?
N2 S1 C16 C17 122.3(3) . . . . ?
O5 S1 C16 C21 54.5(3) . . . . ?
O4 S1 C16 C21 -176.0(3) . . . . ?
N2 S1 C16 C21 -59.3(3) . . . . ?
C21 C16 C17 C18 -1.2(5) . . . . ?
S1 C16 C17 C18 177.2(3) . . . . ?
C10 C11 C12 C13 -1.0(5) . . . . ?
C14 C13 C12 C11 0.8(5) . . . . ?
C17 C16 C21 C20 0.0(6) . . . . ?
S1 C16 C21 C20 -178.4(3) . . . . ?
C17 C16 C21 Cl2 180.0(3) . . . . ?
S1 C16 C21 Cl2 1.6(5) . . . . ?
C16 C21 C20 C19 0.1(7) . . . . ?
Cl2 C21 C20 C19 -180.0(4) . . . . ?
C21 C20 C19 C18 1.3(8) . . . . ?
C20 C19 C18 C17 -2.6(8) . . . . ?
C20 C19 C18 Cl1 177.6(4) . . . . ?
C16 C17 C18 C19 2.5(6) . . . . ?
C16 C17 C18 Cl1 -177.6(3) . . . . ?

_refine_diff_density_max         0.609
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.052



