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#$Date: 2022-11-14 10:57:03 +0200 (Mon, 14 Nov 2022) $
#$Revision: 279249 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/60/8106075.cif $
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#
# 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.
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data_8106075
loop_
_publ_author_name
'Xi-Shi, Tai'
'Peng-Fei, Li'
'Qing-Yun, Liu'
_publ_section_title
;
 The crystal structure of
 (E)-2-((2-(o-tolylcarbamothioyl)hydrazono)methyl)benzoic acid,
 C16H15N3O2S
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              137
_journal_page_last               138
_journal_paper_doi               10.1515/ncrs-2017-0221
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C16 H15 Cl0 N3 O2 S'
_chemical_formula_weight         313.38
_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
_cell_angle_alpha                98.75(3)
_cell_angle_beta                 106.34(3)
_cell_angle_gamma                91.18(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6394(15)
_cell_length_b                   9.2445(18)
_cell_length_c                   11.428(2)
_cell_measurement_reflns_used    3461
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.6345
_cell_measurement_theta_min      2.4532
_cell_volume                     763.7(3)
_computing_molecular_graphics    DIAMOND
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  bruker-CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7428
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.150
_exptl_absorpt_coefficient_mu    0.222
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0993P)²+0.1492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3139
_reflns_number_total             3461
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0221_suppl.cif
_cod_data_source_block           ww
_cod_database_code               8106075
_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   0.959
_shelx_estimated_absorpt_t_max   0.963
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.48227(5) 0.73308(4) 0.15236(4) 0.04350(16) Uani 1 1 d . . . . .
O1 O 1.18235(17) 0.35086(12) 0.03524(13) 0.0519(3) Uani 1 1 d . . . . .
O2 O 1.37644(17) 0.17585(15) 0.05773(13) 0.0582(4) Uani 1 1 d . . . . .
H2 H 1.4095 0.2088 0.0041 0.087 Uiso 1 1 d R U . . .
N1 N 0.69310(17) 0.51243(14) 0.14418(11) 0.0372(3) Uani 1 1 d . . . . .
H1 H 0.7143 0.5431 0.0818 0.045 Uiso 1 1 d R U . . .
N2 N 0.77189(16) 0.38893(13) 0.18398(11) 0.0340(3) Uani 1 1 d . . . . .
N3 N 0.55869(18) 0.53450(14) 0.30140(11) 0.0384(3) Uani 1 1 d . . . . .
H3 H 0.6132 0.4581 0.3229 0.046 Uiso 1 1 d R U . . .
C1 C 0.7095(3) 0.7827(3) 0.4965(2) 0.0654(5) Uani 1 1 d . . . . .
H1A H 0.7920 0.7159 0.5358 0.098 Uiso 1 1 calc R U . . .
H1B H 0.7248 0.8749 0.5510 0.098 Uiso 1 1 calc R U . . .
H1C H 0.7353 0.7975 0.4215 0.098 Uiso 1 1 calc R U . . .
C2 C 0.5154(2) 0.71973(18) 0.46684(14) 0.0425(3) Uani 1 1 d . . . . .
C3 C 0.3989(3) 0.7791(2) 0.53331(16) 0.0532(4) Uani 1 1 d . . . . .
H3A H 0.4424 0.8578 0.5972 0.064 Uiso 1 1 calc R U . . .
C4 C 0.2198(3) 0.7232(2) 0.50625(16) 0.0557(5) Uani 1 1 d . . . . .
H4 H 0.1445 0.7647 0.5517 0.067 Uiso 1 1 calc R U . . .
C5 C 0.1535(2) 0.6077(2) 0.41326(17) 0.0550(4) Uani 1 1 d . . . . .
H5 H 0.0333 0.5701 0.3953 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2664(2) 0.54647(19) 0.34554(15) 0.0463(4) Uani 1 1 d . . . . .
H6 H 0.2218 0.4677 0.2819 0.056 Uiso 1 1 calc R U . . .
C7 C 0.4450(2) 0.60240(15) 0.37252(13) 0.0357(3) Uani 1 1 d . . . . .
C8 C 0.87311(18) 0.32873(15) 0.12093(13) 0.0332(3) Uani 1 1 d . . . . .
H8 H 0.8941 0.3706 0.0567 0.040 Uiso 1 1 calc R U . . .
C9 C 0.95591(18) 0.19169(14) 0.15207(12) 0.0307(3) Uani 1 1 d . . . . .
C10 C 0.8632(2) 0.09791(16) 0.20312(14) 0.0395(3) Uani 1 1 d . . . . .
H10 H 0.7520 0.1234 0.2157 0.047 Uiso 1 1 calc R U . . .
C11 C 0.9334(2) -0.03187(17) 0.23523(16) 0.0468(4) Uani 1 1 d . . . . .
H11 H 0.8701 -0.0920 0.2700 0.056 Uiso 1 1 calc R U . . .
C12 C 1.0975(3) -0.07247(17) 0.21568(16) 0.0470(4) Uani 1 1 d . . . . .
H12 H 1.1450 -0.1596 0.2374 0.056 Uiso 1 1 calc R U . . .
C13 C 1.1900(2) 0.01715(16) 0.16386(14) 0.0401(3) Uani 1 1 d . . . . .
H13 H 1.3004 -0.0104 0.1510 0.048 Uiso 1 1 calc R U . . .
C14 C 1.12161(18) 0.14855(14) 0.13020(12) 0.0312(3) Uani 1 1 d . . . . .
C15 C 1.22646(19) 0.23649(15) 0.06986(13) 0.0342(3) Uani 1 1 d . . . . .
C16 C 0.58289(18) 0.58518(15) 0.20315(13) 0.0327(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C15 O2 H2 109.5 . .
C16 N1 N2 120.03(12) . .
C16 N1 H1 120.0 . .
N2 N1 H1 120.0 . .
C8 N2 N1 114.58(12) . .
C16 N3 C7 122.71(12) . .
C16 N3 H3 118.6 . .
C7 N3 H3 118.7 . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C7 C2 C3 117.40(15) . .
C7 C2 C1 121.80(15) . .
C3 C2 C1 120.79(16) . .
C4 C3 C2 121.37(16) . .
C4 C3 H3A 119.3 . .
C2 C3 H3A 119.3 . .
C5 C4 C3 120.25(15) . .
C5 C4 H4 119.9 . .
C3 C4 H4 119.9 . .
C4 C5 C6 119.60(16) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C7 C6 C5 120.11(15) . .
C7 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C6 C7 C2 121.27(14) . .
C6 C7 N3 118.46(13) . .
C2 C7 N3 120.27(13) . .
N2 C8 C9 118.74(12) . .
N2 C8 H8 120.6 . .
C9 C8 H8 120.6 . .
C10 C9 C14 118.28(13) . .
C10 C9 C8 118.29(12) . .
C14 C9 C8 123.41(12) . .
C11 C10 C9 121.39(14) . .
C11 C10 H10 119.3 . .
C9 C10 H10 119.3 . .
C10 C11 C12 120.12(15) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C13 C12 C11 119.53(14) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 121.44(14) . .
C12 C13 H13 119.3 . .
C14 C13 H13 119.3 . .
C13 C14 C9 119.21(13) . .
C13 C14 C15 118.11(12) . .
C9 C14 C15 122.67(12) . .
O1 C15 O2 122.30(14) . .
O1 C15 C14 125.02(12) . .
O2 C15 C14 112.68(12) . .
N3 C16 N1 117.25(12) . .
N3 C16 S1 122.68(11) . .
N1 C16 S1 120.07(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C16 1.6825(14) .
O1 C15 1.2062(18) .
O2 C15 1.3185(17) .
O2 H2 0.8200 .
N1 C16 1.3492(18) .
N1 N2 1.3801(16) .
N1 H1 0.8602 .
N2 C8 1.2791(18) .
N3 C16 1.3370(19) .
N3 C7 1.4399(17) .
N3 H3 0.8601 .
C1 C2 1.508(2) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C7 1.386(2) .
C2 C3 1.394(2) .
C3 C4 1.386(3) .
C3 H3A 0.9300 .
C4 C5 1.362(3) .
C4 H4 0.9300 .
C5 C6 1.388(2) .
C5 H5 0.9300 .
C6 C7 1.382(2) .
C6 H6 0.9300 .
C8 C9 1.4749(18) .
C8 H8 0.9300 .
C9 C10 1.398(2) .
C9 C14 1.4115(18) .
C10 C11 1.382(2) .
C10 H10 0.9300 .
C11 C12 1.383(2) .
C11 H11 0.9300 .
C12 C13 1.377(2) .
C12 H12 0.9300 .
C13 C14 1.3970(19) .
C13 H13 0.9300 .
C14 C15 1.494(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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C16 N1 N2 C8 179.76(13) . . . .
C7 C2 C3 C4 0.0(3) . . . .
C1 C2 C3 C4 179.35(19) . . . .
C2 C3 C4 C5 0.1(3) . . . .
C3 C4 C5 C6 -0.1(3) . . . .
C4 C5 C6 C7 0.1(3) . . . .
C5 C6 C7 C2 0.0(3) . . . .
C5 C6 C7 N3 179.08(15) . . . .
C3 C2 C7 C6 0.0(2) . . . .
C1 C2 C7 C6 -179.42(17) . . . .
C3 C2 C7 N3 -179.08(14) . . . .
C1 C2 C7 N3 1.5(2) . . . .
C16 N3 C7 C6 95.83(18) . . . .
C16 N3 C7 C2 -85.11(19) . . . .
N1 N2 C8 C9 -176.88(11) . . . .
N2 C8 C9 C10 29.34(18) . . . .
N2 C8 C9 C14 -152.28(13) . . . .
C14 C9 C10 C11 1.9(2) . . . .
C8 C9 C10 C11 -179.59(14) . . . .
C9 C10 C11 C12 -0.8(2) . . . .
C10 C11 C12 C13 -0.1(3) . . . .
C11 C12 C13 C14 -0.1(2) . . . .
C12 C13 C14 C9 1.3(2) . . . .
C12 C13 C14 C15 -177.57(14) . . . .
C10 C9 C14 C13 -2.14(19) . . . .
C8 C9 C14 C13 179.48(12) . . . .
C10 C9 C14 C15 176.65(12) . . . .
C8 C9 C14 C15 -1.7(2) . . . .
C13 C14 C15 O1 179.31(14) . . . .
C9 C14 C15 O1 0.5(2) . . . .
C13 C14 C15 O2 -0.79(19) . . . .
C9 C14 C15 O2 -179.59(13) . . . .
C7 N3 C16 N1 179.81(13) . . . .
C7 N3 C16 S1 -0.2(2) . . . .
N2 N1 C16 N3 1.6(2) . . . .
N2 N1 C16 S1 -178.35(10) . . . .
