#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/76/2227672.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227672
loop_
_publ_author_name
'Ebenezer, Samuel'
'Muthiah, Packianathan Thomas'
_publ_section_title
;
 4-[(2-Hydroxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide:
 a monoclinic polymorph
;
_journal_coeditor_code           IS2595
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2574
_journal_paper_doi               10.1107/S1600536810036585
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H15 N3 O4 S'
_chemical_formula_moiety         'C17 H15 N3 O4 S'
_chemical_formula_sum            'C17 H15 N3 O4 S'
_chemical_formula_weight         357.39
_chemical_name_systematic
4-[(2-Hydroxybenzylidene)amino]-N-(5-methylisoxazol-3-yl)benzenesulfonamide
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 112.9620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.03740(10)
_cell_length_b                   17.9244(3)
_cell_length_c                   14.5175(3)
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      1.9
_cell_volume                     1686.15(5)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0384
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14935
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        24.95
_diffrn_reflns_theta_max         24.95
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       PRISM
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.9817P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1035
_refine_ls_wR_factor_ref         0.1151
_reflns_number_gt                2198
_reflns_number_total             2953
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2595.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227672
_cod_database_fobs_code          2227672
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
S S1 0.61583(11) 0.37355(3) 0.87561(5) 0.0507(3) Uani . . 1.000
O O1 0.8540(3) 0.47399(10) 0.37502(16) 0.0676(8) Uani . . 1.000
O O2 0.3998(3) 0.38398(10) 0.84707(15) 0.0625(7) Uani . . 1.000
O O3 0.7159(3) 0.30911(10) 0.93038(15) 0.0667(8) Uani . . 1.000
O O4 0.7150(3) 0.63662(10) 0.93497(15) 0.0658(7) Uani . . 1.000
N N1 0.8210(4) 0.39344(12) 0.51746(17) 0.0551(8) Uani . . 1.000
N N2 0.7352(3) 0.44313(11) 0.94686(16) 0.0501(8) Uani . . 1.000
N N3 0.8188(4) 0.56808(12) 0.96244(18) 0.0594(9) Uani . . 1.000
C C1 0.9847(4) 0.42129(14) 0.3684(2) 0.0528(10) Uani . . 1.000
C C2 1.0800(5) 0.43213(17) 0.3024(2) 0.0664(11) Uani . . 1.000
C C3 1.2136(6) 0.38013(19) 0.2939(3) 0.0770(14) Uani . . 1.000
C C4 1.2539(6) 0.31558(19) 0.3500(3) 0.0787(16) Uani . . 1.000
C C5 1.1614(5) 0.30449(15) 0.4157(2) 0.0650(11) Uani . . 1.000
C C6 1.0262(4) 0.35658(13) 0.4270(2) 0.0495(9) Uani . . 1.000
C C7 0.9426(4) 0.34594(15) 0.5023(2) 0.0549(10) Uani . . 1.000
C C8 0.7705(4) 0.38551(14) 0.6022(2) 0.0506(9) Uani . . 1.000
C C9 0.5773(4) 0.40732(14) 0.5957(2) 0.0544(10) Uani . . 1.000
C C10 0.5264(4) 0.40347(14) 0.6783(2) 0.0511(10) Uani . . 1.000
C C11 0.6728(4) 0.37909(13) 0.7690(2) 0.0459(8) Uani . . 1.000
C C12 0.8681(4) 0.35926(15) 0.7762(2) 0.0544(10) Uani . . 1.000
C C13 0.9170(4) 0.36252(15) 0.6943(2) 0.0561(10) Uani . . 1.000
C C14 0.6769(4) 0.51741(13) 0.92693(19) 0.0447(9) Uani . . 1.000
C C15 0.4810(4) 0.54900(15) 0.8754(2) 0.0543(10) Uani . . 1.000
C C16 0.5134(4) 0.62267(15) 0.8831(2) 0.0551(10) Uani . . 1.000
C C17 0.3782(5) 0.68894(17) 0.8475(3) 0.0798(13) Uani . . 1.000
H H1 0.81330 0.46250 0.41890 0.1010 Uiso . R 1.000
H H2 1.05290 0.47510 0.26360 0.0800 Uiso calc R 1.000
H H2A 0.84130 0.43320 1.00030 0.0600 Uiso . R 1.000
H H3 1.27820 0.38830 0.24980 0.0920 Uiso calc R 1.000
H H4 1.34340 0.27990 0.34300 0.0940 Uiso calc R 1.000
H H5 1.18960 0.26110 0.45380 0.0780 Uiso calc R 1.000
H H7 0.97800 0.30310 0.54140 0.0660 Uiso calc R 1.000
H H9 0.48080 0.42480 0.53520 0.0650 Uiso calc R 1.000
H H10 0.39510 0.41710 0.67330 0.0610 Uiso calc R 1.000
H H12 0.96640 0.34360 0.83730 0.0650 Uiso calc R 1.000
H H13 1.04890 0.34940 0.69990 0.0670 Uiso calc R 1.000
H H15 0.35650 0.52420 0.84310 0.0650 Uiso calc R 1.000
H H17A 0.39730 0.71040 0.79110 0.1200 Uiso calc R 1.000
H H17B 0.41320 0.72510 0.90030 0.1200 Uiso calc R 1.000
H H17C 0.23670 0.67420 0.82810 0.1200 Uiso calc R 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 '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'
N N 0.0061 0.0033 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 . . . 120.58(13) no
O2 S1 N2 . . . 108.18(12) no
O2 S1 C11 . . . 108.84(13) no
O3 S1 N2 . . . 104.27(12) no
O3 S1 C11 . . . 107.86(13) no
N2 S1 C11 . . . 106.23(12) no
N3 O4 C16 . . . 108.3(2) no
C1 O1 H1 . . . 110.00 no
C7 N1 C8 . . . 119.5(2) no
S1 N2 C14 . . . 124.33(18) no
O4 N3 C14 . . . 105.4(2) no
S1 N2 H2A . . . 118.00 no
C14 N2 H2A . . . 118.00 no
C2 C1 C6 . . . 119.7(3) no
O1 C1 C6 . . . 121.6(3) no
O1 C1 C2 . . . 118.7(2) no
C1 C2 C3 . . . 120.4(3) no
C2 C3 C4 . . . 120.7(4) no
C3 C4 C5 . . . 119.4(4) no
C4 C5 C6 . . . 121.4(3) no
C5 C6 C7 . . . 120.1(2) no
C1 C6 C5 . . . 118.4(3) no
C1 C6 C7 . . . 121.3(2) no
N1 C7 C6 . . . 122.5(2) no
N1 C8 C9 . . . 119.1(2) no
N1 C8 C13 . . . 121.4(3) no
C9 C8 C13 . . . 119.3(3) no
C8 C9 C10 . . . 120.5(3) no
C9 C10 C11 . . . 119.4(3) no
S1 C11 C12 . . . 118.9(2) no
S1 C11 C10 . . . 121.1(2) no
C10 C11 C12 . . . 120.0(3) no
C11 C12 C13 . . . 120.3(3) no
C8 C13 C12 . . . 120.4(3) no
N3 C14 C15 . . . 111.9(2) no
N2 C14 N3 . . . 117.9(3) no
N2 C14 C15 . . . 130.2(2) no
C14 C15 C16 . . . 104.7(2) no
O4 C16 C15 . . . 109.8(2) no
O4 C16 C17 . . . 116.1(2) no
C15 C16 C17 . . . 134.1(3) no
C1 C2 H2 . . . 120.00 no
C3 C2 H2 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C4 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 120.00 no
C5 C4 H4 . . . 120.00 no
C4 C5 H5 . . . 119.00 no
C6 C5 H5 . . . 119.00 no
N1 C7 H7 . . . 119.00 no
C6 C7 H7 . . . 119.00 no
C8 C9 H9 . . . 120.00 no
C10 C9 H9 . . . 120.00 no
C9 C10 H10 . . . 120.00 no
C11 C10 H10 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C8 C13 H13 . . . 120.00 no
C12 C13 H13 . . . 120.00 no
C14 C15 H15 . . . 128.00 no
C16 C15 H15 . . . 128.00 no
C16 C17 H17A . . . 109.00 no
C16 C17 H17B . . . 109.00 no
C16 C17 H17C . . . 109.00 no
H17A C17 H17B . . . 109.00 no
H17A C17 H17C . . . 110.00 no
H17B C17 H17C . . . 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . . 1.424(2) no
S1 O3 . . 1.423(2) no
S1 N2 . . 1.629(2) no
S1 C11 . . 1.747(3) no
O1 C1 . . 1.348(3) no
O4 N3 . . 1.405(3) no
O4 C16 . . 1.345(4) no
O1 H1 . . 0.8200 no
N1 C7 . . 1.286(4) no
N1 C8 . . 1.415(4) no
N2 C14 . . 1.390(3) no
N3 C14 . . 1.299(4) no
N2 H2A . . 0.8600 no
C1 C2 . . 1.381(4) no
C1 C6 . . 1.400(4) no
C2 C3 . . 1.363(5) no
C3 C4 . . 1.379(5) no
C4 C5 . . 1.363(5) no
C5 C6 . . 1.388(4) no
C6 C7 . . 1.442(4) no
C8 C13 . . 1.395(4) no
C8 C9 . . 1.382(4) no
C9 C10 . . 1.381(4) no
C10 C11 . . 1.388(4) no
C11 C12 . . 1.384(4) no
C12 C13 . . 1.362(4) no
C14 C15 . . 1.406(4) no
C15 C16 . . 1.337(4) no
C16 C17 . . 1.483(4) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7 . . 0.9300 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C15 H15 . . 0.9300 no
C17 H17A . . 0.9600 no
C17 H17B . . 0.9600 no
C17 H17C . . 0.9600 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
S1 H15 3.1900 . . no
O1 N1 2.606(3) . . no
O1 N1 3.245(3) . 3_766 no
O1 C10 3.313(3) . 3_666 no
O2 C13 3.276(4) . 1_455 no
O2 C15 3.010(3) . . no
O3 C7 3.172(3) . 4_555 no
O1 H10 2.5300 . 3_666 no
O2 H10 2.5800 . . no
O2 H15 2.5300 . . no
O2 H13 2.6300 . 1_455 no
O3 H12 2.6800 . . no
O3 H4 2.9000 . 4_455 no
O3 H7 2.7800 . 4_555 no
O4 H5 2.6800 . 2_756 no
O4 H3 2.7400 . 3_766 no
N1 O1 2.606(3) . . no
N1 O1 3.245(3) . 3_766 no
N2 N3 2.898(4) . 3_767 no
N3 N2 2.898(4) . 3_767 no
N1 H1 1.8800 . . no
N3 H2A 2.2400 . 3_767 no
C2 C8 3.546(4) . 3_766 no
C5 C9 3.581(4) . 1_655 no
C7 O3 3.172(3) . 4_554 no
C8 C2 3.546(4) . 3_766 no
C9 C5 3.581(4) . 1_455 no
C10 O1 3.313(3) . 3_666 no
C13 O2 3.276(4) . 1_655 no
C15 O2 3.010(3) . . no
C2 H17C 2.9800 . 3_666 no
C2 H15 3.0700 . 3_666 no
C5 H12 3.0000 . 4_554 no
C7 H13 2.6700 . . no
C7 H1 2.4100 . . no
C13 H7 2.6400 . . no
C13 H2 2.9600 . 3_766 no
C16 H3 2.8500 . 3_766 no
H1 N1 1.8800 . . no
H1 C7 2.4100 . . no
H2 C13 2.9600 . 3_766 no
H2A N3 2.2400 . 3_767 no
H3 O4 2.7400 . 3_766 no
H3 C16 2.8500 . 3_766 no
H4 O3 2.9000 . 4_654 no
H5 H7 2.4200 . . no
H5 O4 2.6800 . 2_746 no
H7 C13 2.6400 . . no
H7 H5 2.4200 . . no
H7 H13 2.3100 . . no
H7 O3 2.7800 . 4_554 no
H10 O2 2.5800 . . no
H10 O1 2.5300 . 3_666 no
H12 O3 2.6800 . . no
H12 C5 3.0000 . 4_555 no
H13 O2 2.6300 . 1_655 no
H13 C7 2.6700 . . no
H13 H7 2.3100 . . no
H15 S1 3.1900 . . no
H15 O2 2.5300 . . no
H15 C2 3.0700 . 3_666 no
H17C C2 2.9800 . 3_666 no
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
_geom_hbond_publ_flag
O1 H1 N1 . 0.82 1.88 2.606(3) 147 yes
N2 H2A N3 3_767 0.86 2.24 2.898(4) 134 yes
C10 H10 O1 3_666 0.93 2.53 3.313(3) 141 yes
C15 H15 O2 . 0.93 2.53 3.010(3) 112 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 S1 N2 C14 . . . . -44.7(3) no
O3 S1 N2 C14 . . . . -174.2(2) no
C11 S1 N2 C14 . . . . 72.0(3) no
O2 S1 C11 C10 . . . . 10.4(2) no
O2 S1 C11 C12 . . . . -170.1(2) no
O3 S1 C11 C10 . . . . 142.8(2) no
O3 S1 C11 C12 . . . . -37.7(2) no
N2 S1 C11 C10 . . . . -105.9(2) no
N2 S1 C11 C12 . . . . 73.6(2) no
C16 O4 N3 C14 . . . . -0.4(3) no
N3 O4 C16 C15 . . . . -0.1(3) no
N3 O4 C16 C17 . . . . -180.0(3) no
C8 N1 C7 C6 . . . . -170.2(3) no
C7 N1 C8 C9 . . . . -147.2(3) no
C7 N1 C8 C13 . . . . 38.6(4) no
S1 N2 C14 N3 . . . . -152.9(2) no
S1 N2 C14 C15 . . . . 29.5(4) no
O4 N3 C14 N2 . . . . -177.3(2) no
O4 N3 C14 C15 . . . . 0.7(3) no
O1 C1 C2 C3 . . . . 179.8(3) no
C6 C1 C2 C3 . . . . 0.2(5) no
O1 C1 C6 C5 . . . . 179.6(3) no
O1 C1 C6 C7 . . . . -4.6(4) no
C2 C1 C6 C5 . . . . -0.8(4) no
C2 C1 C6 C7 . . . . 175.1(3) no
C1 C2 C3 C4 . . . . 0.8(5) no
C2 C3 C4 C5 . . . . -1.1(6) no
C3 C4 C5 C6 . . . . 0.4(5) no
C4 C5 C6 C1 . . . . 0.5(5) no
C4 C5 C6 C7 . . . . -175.4(3) no
C1 C6 C7 N1 . . . . 2.4(4) no
C5 C6 C7 N1 . . . . 178.2(3) no
N1 C8 C9 C10 . . . . -177.1(2) no
C13 C8 C9 C10 . . . . -2.7(4) no
N1 C8 C13 C12 . . . . 176.3(2) no
C9 C8 C13 C12 . . . . 2.1(4) no
C8 C9 C10 C11 . . . . 1.5(4) no
C9 C10 C11 S1 . . . . 179.81(19) no
C9 C10 C11 C12 . . . . 0.3(4) no
S1 C11 C12 C13 . . . . 179.6(2) no
C10 C11 C12 C13 . . . . -0.9(4) no
C11 C12 C13 C8 . . . . -0.3(4) no
N2 C14 C15 C16 . . . . 177.0(3) no
N3 C14 C15 C16 . . . . -0.7(3) no
C14 C15 C16 O4 . . . . 0.4(3) no
C14 C15 C16 C17 . . . . -179.7(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12553098
