#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/78/2217816.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2217816
loop_
_publ_author_name
'Shad, Hazoor A.'
'Chohan, Zahid H.'
'Tahir, M. Nawaz'
'Khan, Islam Ullah'
_publ_section_title
4-Chloro-2-[(E)-({4-[N-(3,4-dimethylisoxazol-5-yl)sulfamoyl]phenyl}iminio)methyl]phenolate
_journal_coeditor_code           PV2068
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o635
_journal_paper_doi               10.1107/S1600536808005321
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H16 Cl N3 O4 S'
_chemical_formula_moiety         'C18 H16 Cl N3 O4 S'
_chemical_formula_sum            'C18 H16 Cl N3 O4 S'
_chemical_formula_weight         405.85
_chemical_melting_point          509
_chemical_name_systematic
;
4-Chloro-2-[(E)-({4-[N-(3,4-dimethylisoxazol-5-
yl)sulfamoyl]phenyl}iminio)methyl]phenolate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.081(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1871(6)
_cell_length_b                   7.2555(3)
_cell_length_c                   16.6267(7)
_cell_measurement_reflns_used    2465
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.68
_cell_measurement_theta_min      2.17
_cell_volume                     1827.45(13)
_computing_cell_refinement       'APEX2 (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
'WinGx (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.40
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18429
_diffrn_reflns_theta_full        28.60
_diffrn_reflns_theta_max         28.60
_diffrn_reflns_theta_min         1.75
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0423
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.5575P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                3443
_reflns_number_total             4669
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2068.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2217816
_cod_database_fobs_code          2217816
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.87797(4) -0.43370(8) 0.58505(4) 0.06440(19) Uani d . 1
S S1 0.60762(4) 0.99136(7) 0.32843(3) 0.04563(15) Uani d . 1
O O1 0.62180(10) 0.1417(2) 0.64974(8) 0.0504(4) Uani d . 1
O O2 0.68281(11) 1.0347(2) 0.28554(11) 0.0678(5) Uani d . 1
O O3 0.56667(13) 1.1279(2) 0.37529(10) 0.0676(5) Uani d . 1
O O4 0.59283(10) 0.8115(2) 0.14720(8) 0.0529(4) Uani d . 1
N N1 0.67536(10) 0.3239(2) 0.52967(9) 0.0368(3) Uani d . 1
H H1 0.6445(13) 0.312(3) 0.5715(13) 0.044 Uiso d . 1
N N2 0.52879(11) 0.9215(2) 0.26153(10) 0.0400(4) Uani d . 1
H H2 0.4845(15) 0.908(3) 0.2832(13) 0.048 Uiso d . 1
N N3 0.59687(15) 0.6461(3) 0.10209(12) 0.0666(6) Uani d . 1
C C1 0.73875(12) 0.0376(3) 0.57297(11) 0.0378(4) Uani d . 1
C C2 0.68045(13) 0.0167(3) 0.63625(11) 0.0395(4) Uani d . 1
C C3 0.68941(15) -0.1451(3) 0.68403(12) 0.0471(5) Uani d . 1
H H3 0.6540 -0.1608 0.7269 0.057 Uiso calc R 1
C C4 0.74946(15) -0.2786(3) 0.66788(12) 0.0496(5) Uani d . 1
H H4 0.7533 -0.3850 0.6991 0.059 Uiso calc R 1
C C5 0.80496(13) -0.2571(3) 0.60509(12) 0.0449(4) Uani d . 1
C C6 0.80079(12) -0.1021(3) 0.55890(12) 0.0438(4) Uani d . 1
H H6 0.8389 -0.0879 0.5179 0.053 Uiso calc R 1
C C7 0.73313(12) 0.1937(3) 0.52144(11) 0.0392(4) Uani d . 1
H H7 0.7717 0.2033 0.4807 0.047 Uiso calc R 1
C C8 0.66304(11) 0.4819(2) 0.48013(10) 0.0343(4) Uani d . 1
C C9 0.60243(11) 0.6121(3) 0.50340(10) 0.0360(4) Uani d . 1
H H9 0.5724 0.5928 0.5495 0.043 Uiso calc R 1
C C10 0.58692(12) 0.7701(3) 0.45801(11) 0.0388(4) Uani d . 1
H H10 0.5463 0.8572 0.4732 0.047 Uiso calc R 1
C C11 0.63252(12) 0.7973(3) 0.38967(10) 0.0366(4) Uani d . 1
C C12 0.69331(13) 0.6678(3) 0.36602(11) 0.0425(4) Uani d . 1
H H12 0.7239 0.6883 0.3203 0.051 Uiso calc R 1
C C13 0.70799(13) 0.5089(3) 0.41075(11) 0.0423(4) Uani d . 1
H H13 0.7475 0.4206 0.3947 0.051 Uiso calc R 1
C C14 0.54518(11) 0.7736(3) 0.21080(10) 0.0373(4) Uani d . 1
C C15 0.51814(13) 0.5968(3) 0.20979(11) 0.0417(4) Uani d . 1
C C16 0.55223(16) 0.5232(3) 0.13954(13) 0.0537(5) Uani d . 1
C C17 0.46521(19) 0.4975(3) 0.26793(16) 0.0662(7) Uani d . 1
H H17A 0.4152 0.4405 0.2394 0.099 Uiso calc R 1
H H17B 0.4453 0.5832 0.3067 0.099 Uiso calc R 1
H H17C 0.5010 0.4045 0.2952 0.099 Uiso calc R 1
C C18 0.5413(2) 0.3294(4) 0.10901(18) 0.0851(9) Uani d . 1
H H18A 0.5263 0.3313 0.0519 0.128 Uiso calc R 1
H H18B 0.4951 0.2697 0.1357 0.128 Uiso calc R 1
H H18C 0.5956 0.2631 0.1198 0.128 Uiso calc R 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 121.02(11) n
O2 S1 N2 107.38(10) n
O3 S1 N2 104.86(10) n
O2 S1 C11 108.61(10) n
O3 S1 C11 108.80(9) n
N2 S1 C11 105.00(8) n
C14 O4 N3 106.69(15) n
C7 N1 C8 126.00(15) n
C7 N1 H1 114.5(14) n
C8 N1 H1 119.4(14) n
C14 N2 S1 119.29(13) n
C14 N2 H2 111.7(17) n
S1 N2 H2 109.3(16) n
C16 N3 O4 106.39(16) n
C6 C1 C7 118.96(16) n
C6 C1 C2 119.99(17) n
C7 C1 C2 121.00(17) n
O1 C2 C3 121.31(17) n
O1 C2 C1 121.30(17) n
C3 C2 C1 117.38(18) n
C4 C3 C2 120.93(18) n
C4 C3 H3 119.5 n
C2 C3 H3 119.5 n
C3 C4 C5 120.87(18) n
C3 C4 H4 119.6 n
C5 C4 H4 119.6 n
C6 C5 C4 120.53(19) n
C6 C5 Cl1 120.31(16) n
C4 C5 Cl1 119.15(16) n
C5 C6 C1 120.25(18) n
C5 C6 H6 119.9 n
C1 C6 H6 119.9 n
N1 C7 C1 121.81(16) n
N1 C7 H7 119.1 n
C1 C7 H7 119.1 n
C9 C8 C13 120.42(16) n
C9 C8 N1 116.75(15) n
C13 C8 N1 122.83(16) n
C10 C9 C8 120.05(16) n
C10 C9 H9 120.0 n
C8 C9 H9 120.0 n
C9 C10 C11 119.31(17) n
C9 C10 H10 120.3 n
C11 C10 H10 120.3 n
C10 C11 C12 121.02(17) n
C10 C11 S1 119.21(14) n
C12 C11 S1 119.64(13) n
C13 C12 C11 119.70(16) n
C13 C12 H12 120.1 n
C11 C12 H12 120.1 n
C12 C13 C8 119.50(17) n
C12 C13 H13 120.3 n
C8 C13 H13 120.3 n
C15 C14 O4 111.35(17) n
C15 C14 N2 132.18(16) n
O4 C14 N2 116.35(16) n
C14 C15 C16 103.91(17) n
C14 C15 C17 129.22(19) n
C16 C15 C17 126.9(2) n
N3 C16 C15 111.7(2) n
N3 C16 C18 121.8(2) n
C15 C16 C18 126.5(2) n
C15 C17 H17A 109.5 n
C15 C17 H17B 109.5 n
H17A C17 H17B 109.5 n
C15 C17 H17C 109.5 n
H17A C17 H17C 109.5 n
H17B C17 H17C 109.5 n
C16 C18 H18A 109.5 n
C16 C18 H18B 109.5 n
H18A C18 H18B 109.5 n
C16 C18 H18C 109.5 n
H18A C18 H18C 109.5 n
H18B C18 H18C 109.5 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C5 1.742(2) n
S1 O2 1.4238(17) n
S1 O3 1.4298(17) n
S1 N2 1.6545(17) n
S1 C11 1.7630(18) n
O1 C2 1.302(2) n
O4 C14 1.351(2) n
O4 N3 1.419(2) n
N1 C7 1.303(2) n
N1 C8 1.416(2) n
N1 H1 0.87(2) n
N2 C14 1.399(2) n
N2 H2 0.79(2) n
N3 C16 1.305(3) n
C1 C6 1.415(3) n
C1 C7 1.419(3) n
C1 C2 1.431(2) n
C2 C3 1.419(3) n
C3 C4 1.370(3) n
C3 H3 0.9300 n
C4 C5 1.396(3) n
C4 H4 0.9300 n
C5 C6 1.361(3) n
C6 H6 0.9300 n
C7 H7 0.9300 n
C8 C9 1.393(2) n
C8 C13 1.395(2) n
C9 C10 1.383(3) n
C9 H9 0.9300 n
C10 C11 1.386(2) n
C10 H10 0.9300 n
C11 C12 1.393(3) n
C12 C13 1.382(3) n
C12 H12 0.9300 n
C13 H13 0.9300 n
C14 C15 1.346(3) n
C15 C16 1.415(3) n
C15 C17 1.487(3) n
C16 C18 1.501(3) n
C17 H17A 0.9600 n
C17 H17B 0.9600 n
C17 H17C 0.9600 n
C18 H18A 0.9600 n
C18 H18B 0.9600 n
C18 H18C 0.9600 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O1 1_555 0.87(2) 1.85(2) 2.574(2) 140(2)
C7 H7 N3 2_645 0.93 2.54 3.429(3) 161
C12 H12 O2 2_645 0.93 2.59 3.391(3) 145
C17 H17C O3 1_545 0.96 2.57 3.516(3) 168
C17 H17B O1 3_666 0.96 2.38 3.276(3) 156
N2 H2 O1 3_666 0.79(2) 2.06(2) 2.846(2) 173(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_publ_flag
O2 S1 N2 C14 56.27(16) n
O3 S1 N2 C14 -173.81(14) n
C11 S1 N2 C14 -59.20(15) n
C14 O4 N3 C16 0.6(2) n
C6 C1 C2 O1 -178.92(18) n
C7 C1 C2 O1 -1.5(3) n
C6 C1 C2 C3 1.4(3) n
C7 C1 C2 C3 178.83(18) n
O1 C2 C3 C4 177.98(19) n
C1 C2 C3 C4 -2.4(3) n
C2 C3 C4 C5 1.5(3) n
C3 C4 C5 C6 0.4(3) n
C3 C4 C5 Cl1 -178.14(16) n
C4 C5 C6 C1 -1.3(3) n
Cl1 C5 C6 C1 177.20(15) n
C7 C1 C6 C5 -177.06(18) n
C2 C1 C6 C5 0.4(3) n
C8 N1 C7 C1 -178.19(17) n
C6 C1 C7 N1 177.69(19) n
C2 C1 C7 N1 0.3(3) n
C7 N1 C8 C9 -174.85(18) n
C7 N1 C8 C13 5.6(3) n
C13 C8 C9 C10 -0.5(3) n
N1 C8 C9 C10 179.96(16) n
C8 C9 C10 C11 -0.3(3) n
C9 C10 C11 C12 0.2(3) n
C9 C10 C11 S1 176.02(14) n
O2 S1 C11 C10 155.29(15) n
O3 S1 C11 C10 21.74(19) n
N2 S1 C11 C10 -90.09(16) n
O2 S1 C11 C12 -28.85(19) n
O3 S1 C11 C12 -162.40(16) n
N2 S1 C11 C12 85.77(17) n
C10 C11 C12 C13 0.6(3) n
S1 C11 C12 C13 -175.17(16) n
C11 C12 C13 C8 -1.4(3) n
C9 C8 C13 C12 1.3(3) n
N1 C8 C13 C12 -179.16(18) n
N3 O4 C14 C15 -0.2(2) n
N3 O4 C14 N2 -176.68(17) n
S1 N2 C14 C15 105.9(2) n
S1 N2 C14 O4 -78.51(19) n
O4 C14 C15 C16 -0.2(2) n
N2 C14 C15 C16 175.5(2) n
O4 C14 C15 C17 179.5(2) n
N2 C14 C15 C17 -4.7(4) n
O4 N3 C16 C15 -0.7(3) n
O4 N3 C16 C18 179.6(3) n
C14 C15 C16 N3 0.6(3) n
C17 C15 C16 N3 -179.2(2) n
C14 C15 C16 C18 -179.8(3) n
C17 C15 C16 C18 0.4(4) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655452
