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#$Date: 2021-07-10 07:41:05 +0300 (Sat, 10 Jul 2021) $
#$Revision: 267456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243864.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_2243864
loop_
_publ_author_name
'Purandara, H.'
'Foro, Sabine'
'Thimme Gowda, B.'
_publ_section_title
;
 Crystal structures of three N-acylhydrazone isomers
;
_journal_coeditor_code           MW2177
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              780
_journal_page_last               784
_journal_paper_doi               10.1107/S2056989021006885
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C15 H13 Cl2 N3 O3 S'
_chemical_formula_moiety         'C15 H13 Cl2 N3 O3 S'
_chemical_formula_sum            'C15 H13 Cl2 N3 O3 S'
_chemical_formula_weight         386.24
_chemical_name_systematic
(E)-4-Chloro-N-{2-[2-(3-chlorobenzylidene)hydrazinyl]-2-oxoethyl}benzenesulfonamide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL2014/6
_cell_angle_alpha                67.220(10)
_cell_angle_beta                 66.800(10)
_cell_angle_gamma                86.320(10)
_cell_formula_units_Z            2
_cell_length_a                   9.4910(10)
_cell_length_b                   9.9760(10)
_cell_length_c                   10.4460(10)
_cell_measurement_reflns_used    2850
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.93
_cell_measurement_theta_min      2.55
_cell_volume                     833.59(18)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014/6 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013/1 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur with Sapphire CCD
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5759
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.548
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.534
_exptl_absorpt_correction_T_max  0.9585
_exptl_absorpt_correction_T_min  0.8311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED, Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.216
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.216
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0148P)²+1.1114P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2688
_reflns_number_total             3354
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            mw2177sup1.cif
_cod_data_source_block           II
_cod_original_cell_volume        833.59(17)
_cod_database_code               2243864
_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.
;
_shelx_estimated_absorpt_t_min   0.831
_shelx_estimated_absorpt_t_max   0.959
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2520(3) -0.1930(3) 1.0295(3) 0.0312(6) Uani d 1 . .
C C2 0.1178(3) -0.2828(3) 1.0900(4) 0.0408(7) Uani d 1 . .
H H2 0.0241 -0.2549 1.1415 0.049 Uiso calc 1 . .
C C3 0.1226(4) -0.4145(4) 1.0739(4) 0.0458(8) Uani d 1 . .
H H3 0.0329 -0.4769 1.1166 0.055 Uiso calc 1 . .
C C4 0.2616(4) -0.4519(3) 0.9939(4) 0.0392(7) Uani d 1 . .
C C5 0.3966(4) -0.3626(3) 0.9327(4) 0.0393(7) Uani d 1 . .
H H5 0.4898 -0.3896 0.8789 0.047 Uiso calc 1 . .
C C6 0.3924(3) -0.2326(3) 0.9519(3) 0.0356(7) Uani d 1 . .
H H6 0.4828 -0.1724 0.9131 0.043 Uiso calc 1 . .
C C7 0.2808(3) 0.1427(3) 0.7715(3) 0.0356(7) Uani d 1 . .
H H7A 0.2814 0.2480 0.7273 0.043 Uiso calc 1 . .
H H7B 0.1751 0.0995 0.8162 0.043 Uiso calc 1 . .
C C8 0.3771(3) 0.0903(3) 0.6490(3) 0.0351(7) Uani d 1 . .
C C9 0.1510(4) 0.1675(4) 0.4412(3) 0.0414(7) Uani d 1 . .
H H9 0.2108 0.1262 0.3740 0.050 Uiso calc 1 . .
C C10 0.0084(4) 0.2250(3) 0.4311(3) 0.0400(7) Uani d 1 . .
C C11 -0.0769(4) 0.3041(4) 0.5152(4) 0.0469(8) Uani d 1 . .
H H11 -0.0426 0.3245 0.5783 0.056 Uiso calc 1 . .
C C12 -0.2121(4) 0.3515(4) 0.5037(4) 0.0540(9) Uani d 1 . .
C C13 -0.2654(4) 0.3247(4) 0.4096(5) 0.0600(10) Uani d 1 . .
H H13 -0.3566 0.3589 0.4022 0.072 Uiso calc 1 . .
C C14 -0.1815(5) 0.2467(4) 0.3273(5) 0.0603(10) Uani d 1 . .
H H14 -0.2165 0.2274 0.2640 0.072 Uiso calc 1 . .
C C15 -0.0459(4) 0.1966(4) 0.3371(4) 0.0497(8) Uani d 1 . .
H H15 0.0097 0.1435 0.2808 0.060 Uiso calc 1 . .
Cl Cl1 0.26935(11) -0.61454(10) 0.96808(12) 0.0584(3) Uani d 1 . .
Cl Cl2 -0.32203(15) 0.44557(16) 0.61290(17) 0.0976(5) Uani d 1 . .
N N1 0.3402(3) 0.1031(3) 0.8891(3) 0.0318(5) Uani d 1 . .
H H1N 0.436(2) 0.101(3) 0.860(3) 0.038 Uiso d 1 . .
N N2 0.3309(3) 0.1124(3) 0.5371(3) 0.0436(7) Uani d 1 . .
H H2N 0.378(4) 0.072(4) 0.474(3) 0.052 Uiso d 1 . .
N N3 0.1952(3) 0.1727(3) 0.5398(3) 0.0394(6) Uani d 1 . .
O O1 0.3340(2) -0.0350(2) 1.1413(2) 0.0411(5) Uani d 1 . .
O O2 0.0898(2) 0.0034(2) 1.1055(2) 0.0408(5) Uani d 1 . .
O O3 0.4936(2) 0.0311(3) 0.6515(2) 0.0475(6) Uani d 1 . .
S S1 0.24739(8) -0.02589(8) 1.05320(8) 0.03071(18) Uani d 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'
Cl Cl 0.1484 0.1585 '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'
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_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.8(3) ?
C2 C1 S1 . . 120.2(2) ?
C6 C1 S1 . . 119.0(2) ?
C1 C2 C3 . . 119.9(3) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 119.1(3) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 C5 . . 121.4(3) ?
C3 C4 Cl1 . . 119.8(2) ?
C5 C4 Cl1 . . 118.8(2) ?
C4 C5 C6 . . 119.5(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 119.3(3) ?
C5 C6 H6 . . 120.4 ?
C1 C6 H6 . . 120.4 ?
N1 C7 C8 . . 111.0(2) ?
N1 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
N1 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
O3 C8 N2 . . 121.4(3) ?
O3 C8 C7 . . 121.1(3) ?
N2 C8 C7 . . 117.5(3) ?
N3 C9 C10 . . 121.6(3) ?
N3 C9 H9 . . 119.2 ?
C10 C9 H9 . . 119.2 ?
C15 C10 C11 . . 119.0(3) ?
C15 C10 C9 . . 118.8(3) ?
C11 C10 C9 . . 122.2(3) ?
C12 C11 C10 . . 119.3(3) ?
C12 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?
C11 C12 C13 . . 121.9(4) ?
C11 C12 Cl2 . . 119.4(3) ?
C13 C12 Cl2 . . 118.7(3) ?
C14 C13 C12 . . 118.7(3) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C13 C14 C15 . . 120.9(4) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C14 C15 C10 . . 120.3(4) ?
C14 C15 H15 . . 119.9 ?
C10 C15 H15 . . 119.9 ?
C7 N1 S1 . . 119.9(2) ?
C7 N1 H1N . . 116(2) ?
S1 N1 H1N . . 112(2) ?
C8 N2 N3 . . 120.8(2) ?
C8 N2 H2N . . 117(2) ?
N3 N2 H2N . . 121(2) ?
C9 N3 N2 . . 115.1(3) ?
O2 S1 O1 . . 119.53(13) ?
O2 S1 N1 . . 107.80(13) ?
O1 S1 N1 . . 105.65(13) ?
O2 S1 C1 . . 107.23(13) ?
O1 S1 C1 . . 107.84(13) ?
N1 S1 C1 . . 108.40(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.377(4) ?
C1 C6 . 1.385(4) ?
C1 S1 . 1.773(3) ?
C2 C3 . 1.384(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.374(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(4) ?
C4 Cl1 . 1.737(3) ?
C5 C6 . 1.382(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.457(4) ?
C7 C8 . 1.510(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O3 . 1.224(3) ?
C8 N2 . 1.342(4) ?
C9 N3 . 1.275(4) ?
C9 C10 . 1.462(4) ?
C9 H9 . 0.9300 ?
C10 C15 . 1.394(4) ?
C10 C11 . 1.394(4) ?
C11 C12 . 1.372(5) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.381(5) ?
C12 Cl2 . 1.743(4) ?
C13 C14 . 1.370(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.378(5) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
N1 S1 . 1.618(3) ?
N1 H1N . 0.841(17) ?
N2 N3 . 1.380(3) ?
N2 H2N . 0.863(18) ?
O1 S1 . 1.433(2) ?
O2 S1 . 1.430(2) ?
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 H1N O1 2_657 0.841(17) 2.23(2) 3.041(3) 161(3)
N2 H2N O3 2_656 0.863(18) 1.972(19) 2.828(3) 171(3)
C6 H6 O1 2_657 0.93 2.53 3.422(4) 160.6
C7 H7B O2 2_557 0.97 2.47 3.434(4) 172.3
C15 H15 O2 1_554 0.93 2.58 3.474(4) 162.3
C14 H14 Cg 2_556 0.93 2.84 3.675(5) 150
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
C6 C1 C2 C3 . . . . 0.2(5) ?
S1 C1 C2 C3 . . . . -178.6(3) ?
C1 C2 C3 C4 . . . . -1.7(5) ?
C2 C3 C4 C5 . . . . 1.5(5) ?
C2 C3 C4 Cl1 . . . . -178.3(3) ?
C3 C4 C5 C6 . . . . 0.0(5) ?
Cl1 C4 C5 C6 . . . . 179.8(2) ?
C4 C5 C6 C1 . . . . -1.4(5) ?
C2 C1 C6 C5 . . . . 1.3(5) ?
S1 C1 C6 C5 . . . . -179.8(2) ?
N1 C7 C8 O3 . . . . -4.1(4) ?
N1 C7 C8 N2 . . . . 176.5(3) ?
N3 C9 C10 C15 . . . . -170.4(3) ?
N3 C9 C10 C11 . . . . 8.0(5) ?
C15 C10 C11 C12 . . . . 0.2(5) ?
C9 C10 C11 C12 . . . . -178.2(3) ?
C10 C11 C12 C13 . . . . -0.8(6) ?
C10 C11 C12 Cl2 . . . . 178.1(3) ?
C11 C12 C13 C14 . . . . 0.9(6) ?
Cl2 C12 C13 C14 . . . . -178.0(3) ?
C12 C13 C14 C15 . . . . -0.4(6) ?
C13 C14 C15 C10 . . . . -0.2(6) ?
C11 C10 C15 C14 . . . . 0.3(5) ?
C9 C10 C15 C14 . . . . 178.7(3) ?
C8 C7 N1 S1 . . . . -107.2(3) ?
O3 C8 N2 N3 . . . . 176.8(3) ?
C7 C8 N2 N3 . . . . -3.8(5) ?
C10 C9 N3 N2 . . . . 179.1(3) ?
C8 N2 N3 C9 . . . . -169.5(3) ?
C7 N1 S1 O2 . . . . -50.2(2) ?
C7 N1 S1 O1 . . . . -179.0(2) ?
C7 N1 S1 C1 . . . . 65.6(2) ?
C2 C1 S1 O2 . . . . -13.7(3) ?
C6 C1 S1 O2 . . . . 167.4(2) ?
C2 C1 S1 O1 . . . . 116.3(3) ?
C6 C1 S1 O1 . . . . -62.6(3) ?
C2 C1 S1 N1 . . . . -129.8(3) ?
C6 C1 S1 N1 . . . . 51.3(3) ?

_cod_database_fobs_code 2243864
