#------------------------------------------------------------------------------
#$Date: 2021-08-04 07:02:52 +0300 (Wed, 04 Aug 2021) $
#$Revision: 267931 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243883.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_2243883
loop_
_publ_author_name
'Azzam, Rasha A.'
'Elgemeie, Galal H.'
'Seif, Mona M.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 N'-[2-(benzo[d]thiazol-2-yl)acetyl]benzohydrazide, an
 achiral compound crystallizing in space group P1 with Z = 1
;
_journal_coeditor_code           YK2155
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989021007672
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C16 H13 N3 O2 S'
_chemical_formula_moiety         'C16 H13 N3 O2 S'
_chemical_formula_sum            'C16 H13 N3 O2 S'
_chemical_formula_weight         311.35
_chemical_name_systematic
;
N'-[2-(Benzo[d]thiazol-2-yl)acetyl]benzohydrazide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                105.6168(18)
_cell_angle_beta                 95.7876(16)
_cell_angle_gamma                95.9993(16)
_cell_formula_units_Z            1
_cell_length_a                   4.71248(9)
_cell_length_b                   6.96463(14)
_cell_length_c                   11.5455(3)
_cell_measurement_reflns_used    40070
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.9870
_cell_measurement_theta_min      3.0320
_cell_volume                     359.638(14)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
 XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'XtaLAB Synergy, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            60895
_diffrn_reflns_theta_full        35.000
_diffrn_reflns_theta_max         36.792
_diffrn_reflns_theta_min         3.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       plate
_exptl_crystal_F_000             162
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.273
_refine_ls_abs_structure_details
;
Flack x determined using 2959 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.016(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         6522
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0486P)²+0.0499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0784
_reflns_number_gt                6312
_reflns_number_total             6522
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yk2155sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        359.637(13)
_cod_database_code               2243883
_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   0.954
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'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
S S1 0.88408(5) 0.86164(4) 0.76703(3) 0.01738(7) Uani d 1 . .
C C2 0.8642(3) 0.87459(17) 0.61788(11) 0.01314(18) Uani d 1 . .
N N1 0.9484(2) 0.36700(15) 0.44206(10) 0.01379(17) Uani d 1 . .
H H01 1.135(6) 0.377(4) 0.440(3) 0.031(6) Uiso d 1 . .
N N2 0.7891(2) 0.17967(15) 0.38503(10) 0.01379(17) Uani d 1 . .
H H02 0.743(6) 0.111(4) 0.433(2) 0.025(6) Uiso d 1 . .
N N3 0.7208(2) 1.01131(16) 0.59308(10) 0.01420(17) Uani d 1 . .
C C3A 0.6136(3) 1.11873(18) 0.69578(11) 0.01407(18) Uani d 1 . .
C C4 0.4492(3) 1.2765(2) 0.70032(13) 0.0202(2) Uani d 1 . .
H H4 0.401227 1.318921 0.630063 0.024 Uiso calc 1 . .
C C5 0.3581(3) 1.3691(2) 0.80960(15) 0.0232(3) Uani d 1 . .
H H5 0.245566 1.475698 0.813913 0.028 Uiso calc 1 . .
C C6 0.4294(3) 1.3082(2) 0.91385(13) 0.0214(2) Uani d 1 . .
H H6 0.364372 1.374379 0.987636 0.026 Uiso calc 1 . .
C C7 0.5928(3) 1.1534(2) 0.91122(12) 0.0191(2) Uani d 1 . .
H H7 0.642508 1.113038 0.982118 0.023 Uiso calc 1 . .
C C7A 0.6821(3) 1.05845(18) 0.80085(11) 0.01465(19) Uani d 1 . .
C C8 1.0007(3) 0.72931(17) 0.52744(11) 0.01505(19) Uani d 1 . .
H H8A 1.188694 0.709803 0.566030 0.018 Uiso calc 1 . .
H H8B 1.035889 0.785089 0.459045 0.018 Uiso calc 1 . .
C C9 0.8084(3) 0.52723(17) 0.47944(11) 0.01345(18) Uani d 1 . .
O O1 0.5458(2) 0.51401(15) 0.47552(10) 0.01766(17) Uani d 1 . .
C C10 0.6341(3) 0.15543(17) 0.27343(11) 0.01340(18) Uani d 1 . .
O O2 0.6698(2) 0.27818(15) 0.21612(10) 0.01878(17) Uani d 1 . .
C C11 0.4201(3) -0.03063(17) 0.22693(11) 0.01309(18) Uani d 1 . .
C C12 0.4296(3) -0.19751(18) 0.27175(12) 0.01574(19) Uani d 1 . .
H H12 0.576152 -0.195084 0.335201 0.019 Uiso calc 1 . .
C C13 0.2252(3) -0.36724(18) 0.22370(12) 0.0172(2) Uani d 1 . .
H H13 0.233253 -0.481009 0.253846 0.021 Uiso calc 1 . .
C C14 0.0089(3) -0.37052(19) 0.13160(12) 0.0180(2) Uani d 1 . .
H H14 -0.132276 -0.485758 0.099661 0.022 Uiso calc 1 . .
C C15 -0.0006(3) -0.2051(2) 0.08620(13) 0.0191(2) Uani d 1 . .
H H15 -0.147919 -0.208041 0.022925 0.023 Uiso calc 1 . .
C C16 0.2046(3) -0.03535(19) 0.13308(12) 0.0164(2) Uani d 1 . .
H H16 0.198429 0.076976 0.101456 0.020 Uiso calc 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'
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
C7A S1 C2 . . 89.49(6) y
N3 C2 C8 . . 124.45(11) ?
N3 C2 S1 . . 115.83(9) y
C8 C2 S1 . . 119.70(9) ?
C9 N1 N2 . . 119.00(10) y
C10 N2 N1 . . 117.28(10) y
C2 N3 C3A . . 110.61(10) y
N3 C3A C4 . . 125.26(11) ?
N3 C3A C7A . . 114.95(11) ?
C4 C3A C7A . . 119.79(12) ?
C5 C4 C3A . . 118.52(13) ?
C4 C5 C6 . . 121.11(13) ?
C7 C6 C5 . . 121.18(13) ?
C6 C7 C7A . . 117.77(13) ?
C7 C7A C3A . . 121.63(12) ?
C7 C7A S1 . . 129.24(10) ?
C3A C7A S1 . . 109.13(9) ?
C2 C8 C9 . . 110.93(10) ?
O1 C9 N1 . . 123.27(11) ?
O1 C9 C8 . . 121.67(11) ?
N1 C9 C8 . . 115.06(10) ?
O2 C10 N2 . . 122.11(11) ?
O2 C10 C11 . . 122.31(11) ?
N2 C10 C11 . . 115.59(10) ?
C12 C11 C16 . . 119.69(11) ?
C12 C11 C10 . . 122.96(11) ?
C16 C11 C10 . . 117.35(10) ?
C13 C12 C11 . . 120.15(11) ?
C14 C13 C12 . . 120.05(11) ?
C13 C14 C15 . . 120.02(11) ?
C14 C15 C16 . . 120.28(12) ?
C15 C16 C11 . . 119.80(11) ?
C9 N1 H01 . . 123.3(19) ?
N2 N1 H01 . . 116.8(19) ?
C10 N2 H02 . . 123.3(18) ?
N1 N2 H02 . . 114.4(18) ?
C5 C4 H4 . . 120.7 ?
C3A C4 H4 . . 120.7 ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C5 C6 H6 . . 119.4 ?
C6 C7 H7 . . 121.1 ?
C7A C7 H7 . . 121.1 ?
C2 C8 H8A . . 109.5 ?
C9 C8 H8A . . 109.5 ?
C2 C8 H8B . . 109.5 ?
C9 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.0 ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C15 C14 H14 . . 120.0 ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C15 C16 H16 . . 120.1 ?
C11 C16 H16 . . 120.1 ?
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
S1 C7A . 1.7310(13) y
S1 C2 . 1.7422(12) y
C2 N3 . 1.2993(16) y
C2 C8 . 1.4933(17) ?
N1 C9 . 1.3488(16) ?
N1 N2 . 1.3901(14) y
N2 C10 . 1.3747(16) ?
N3 C3A . 1.3939(16) y
C3A C4 . 1.4018(18) ?
C3A C7A . 1.4056(17) ?
C4 C5 . 1.386(2) ?
C5 C6 . 1.401(2) ?
C6 C7 . 1.385(2) ?
C7 C7A . 1.3967(19) ?
C8 C9 . 1.5237(16) ?
C9 O1 . 1.2266(15) ?
C10 O2 . 1.2222(14) ?
C10 C11 . 1.4925(16) ?
C11 C12 . 1.3967(17) ?
C11 C16 . 1.3994(17) ?
C12 C13 . 1.3909(17) ?
C13 C14 . 1.390(2) ?
C14 C15 . 1.3911(19) ?
C15 C16 . 1.3919(18) ?
N1 H01 . 0.88(3) ?
N2 H02 . 0.85(3) ?
C4 H4 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
N1 H01 O1 1_655 0.88(3) 2.02(3) 2.8438(14) 157(3) yes
N2 H02 N3 1_545 0.85(3) 2.15(3) 2.9736(15) 162(3) yes
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
C7A S1 C2 N3 . . . . -0.19(10) ?
C7A S1 C2 C8 . . . . -178.46(10) ?
C9 N1 N2 C10 . . . . 66.44(15) y
C8 C2 N3 C3A . . . . 178.23(11) ?
S1 C2 N3 C3A . . . . 0.05(14) ?
C2 N3 C3A C4 . . . . -179.93(12) ?
C2 N3 C3A C7A . . . . 0.16(15) ?
N3 C3A C4 C5 . . . . -179.93(13) ?
C7A C3A C4 C5 . . . . 0.0(2) ?
C3A C4 C5 C6 . . . . 0.4(2) ?
C4 C5 C6 C7 . . . . -0.1(2) ?
C5 C6 C7 C7A . . . . -0.6(2) ?
C6 C7 C7A C3A . . . . 0.96(19) ?
C6 C7 C7A S1 . . . . -179.59(11) ?
N3 C3A C7A C7 . . . . 179.25(12) ?
C4 C3A C7A C7 . . . . -0.65(19) ?
N3 C3A C7A S1 . . . . -0.30(13) ?
C4 C3A C7A S1 . . . . 179.80(10) ?
C2 S1 C7A C7 . . . . -179.25(13) ?
C2 S1 C7A C3A . . . . 0.26(9) ?
N3 C2 C8 C9 . . . . -97.86(14) ?
S1 C2 C8 C9 . . . . 80.26(12) y
N2 N1 C9 O1 . . . . 6.66(18) ?
N2 N1 C9 C8 . . . . -173.21(10) y
C2 C8 C9 O1 . . . . 27.72(16) ?
C2 C8 C9 N1 . . . . -152.41(11) y
N1 N2 C10 O2 . . . . 12.34(18) ?
N1 N2 C10 C11 . . . . -167.79(10) y
O2 C10 C11 C12 . . . . 161.41(13) ?
N2 C10 C11 C12 . . . . -18.46(17) y
O2 C10 C11 C16 . . . . -17.71(18) ?
N2 C10 C11 C16 . . . . 162.42(11) ?
C16 C11 C12 C13 . . . . -0.29(19) ?
C10 C11 C12 C13 . . . . -179.40(12) ?
C11 C12 C13 C14 . . . . -0.6(2) ?
C12 C13 C14 C15 . . . . 0.9(2) ?
C13 C14 C15 C16 . . . . -0.4(2) ?
C14 C15 C16 C11 . . . . -0.5(2) ?
C12 C11 C16 C15 . . . . 0.84(19) ?
C10 C11 C16 C15 . . . . 179.99(12) ?
O1 C9 N1 H01 . . . . 175(2) y
O2 C10 N2 H02 . . . . 166(2) y
H01 N1 N2 H02 . . . . 101(3) y

_cod_database_fobs_code 2243883
