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#$Date: 2023-09-19 10:39:05 +0300 (Tue, 19 Sep 2023) $
#$Revision: 286406 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107517.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_8107517
loop_
_publ_author_name
'Qiao, Ai-Li'
'Guo, Zheng-Feng'
_publ_section_title
;
 The crystal structure of
 (Z)-4-amino-N′-(1-(o-tolyl)ethylidene)benzohydrazide, C16H17N3O
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              639
_journal_page_last               640
_journal_paper_doi               10.1515/ncrs-2023-0127
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C16 H17 N3 O'
_chemical_formula_sum            'C16 H17 N3 O'
_chemical_formula_weight         267.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 98.980(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2818(6)
_cell_length_b                   17.0495(10)
_cell_length_c                   10.2429(7)
_cell_measurement_reflns_used    4260
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6050
_cell_measurement_theta_min      3.7860
_cell_volume                     1428.58(17)
_computing_cell_refinement
'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021) [1]'
_computing_data_collection
'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021) [1]'
_computing_data_reduction
'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021) [1]'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009) [4]'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009) [4]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015) [3]'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018) [2]'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0584
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12434
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.424
_diffrn_reflns_theta_min         3.438
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0629
_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)+(0.0440P)²+0.6026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1461
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2710
_reflns_number_total             3475
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0127_suppl_001.cif
_cod_data_source_block           ab31
_cod_database_code               8107517
_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_max   0.979
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), N1(H1)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
C1 C 1.1080(2) 0.47452(11) 0.70030(18) 0.0413(4) Uani 1 1 d . . . . .
C2 C 1.0699(2) 0.42276(11) 0.59507(18) 0.0405(4) Uani 1 1 d . . . . .
H2 H 1.152267 0.403886 0.551306 0.049 Uiso 1 1 calc R U . . .
C3 C 0.9107(2) 0.39939(10) 0.55551(17) 0.0386(4) Uani 1 1 d . . . . .
H3 H 0.886549 0.365403 0.484110 0.046 Uiso 1 1 calc R U . . .
C4 C 0.7847(2) 0.42568(10) 0.62044(17) 0.0367(4) Uani 1 1 d . . . . .
C5 C 0.8250(2) 0.47533(12) 0.72764(19) 0.0465(5) Uani 1 1 d . . . . .
H5 H 0.743536 0.492480 0.773846 0.056 Uiso 1 1 calc R U . . .
C6 C 0.9835(2) 0.49973(12) 0.76696(19) 0.0487(5) Uani 1 1 d . . . . .
H6 H 1.007552 0.533393 0.838797 0.058 Uiso 1 1 calc R U . . .
C7 C 0.6109(2) 0.40197(10) 0.58340(17) 0.0389(4) Uani 1 1 d . . . . .
C8 C 0.3796(2) 0.32998(11) 0.29338(18) 0.0412(4) Uani 1 1 d . . . . .
C9 C 0.4996(2) 0.32793(11) 0.19883(18) 0.0401(4) Uani 1 1 d . . . . .
C10 C 0.4704(3) 0.37472(13) 0.08604(19) 0.0514(5) Uani 1 1 d . . . . .
H10 H 0.376659 0.405516 0.070957 0.062 Uiso 1 1 calc R U . . .
C11 C 0.5785(3) 0.37599(16) -0.0035(2) 0.0670(7) Uani 1 1 d . . . . .
H11 H 0.558854 0.407820 -0.077996 0.080 Uiso 1 1 calc R U . . .
C12 C 0.7153(4) 0.32982(18) 0.0187(3) 0.0775(8) Uani 1 1 d . . . . .
H12 H 0.789872 0.331197 -0.040361 0.093 Uiso 1 1 calc R U . . .
C13 C 0.7438(3) 0.28139(16) 0.1274(3) 0.0693(7) Uani 1 1 d . . . . .
H13 H 0.836249 0.249654 0.139492 0.083 Uiso 1 1 calc R U . . .
C14 C 0.6368(3) 0.27902(12) 0.2195(2) 0.0495(5) Uani 1 1 d . . . . .
C15 C 0.6665(3) 0.22317(14) 0.3334(3) 0.0710(7) Uani 1 1 d . . . . .
H15A H 0.692902 0.252108 0.414274 0.106 Uiso 1 1 calc R U . . .
H15B H 0.755697 0.189042 0.322754 0.106 Uiso 1 1 calc R U . . .
H15C H 0.569829 0.192505 0.336128 0.106 Uiso 1 1 calc R U . . .
C16 C 0.2093(3) 0.30150(14) 0.2451(2) 0.0589(6) Uani 1 1 d . . . . .
H16A H 0.212469 0.246902 0.222724 0.088 Uiso 1 1 calc R U . . .
H16B H 0.163322 0.330923 0.168313 0.088 Uiso 1 1 calc R U . . .
H16C H 0.143227 0.308460 0.313318 0.088 Uiso 1 1 calc R U . . .
N1 N 0.56549(18) 0.38279(9) 0.45519(14) 0.0419(4) Uani 1 1 d . . . . .
H1 H 0.633360 0.387774 0.400168 0.050 Uiso 1 1 calc R U . . .
N2 N 0.40905(19) 0.35505(10) 0.41259(16) 0.0438(4) Uani 1 1 d . . . . .
N3 N 1.2664(2) 0.50226(13) 0.7339(2) 0.0563(5) Uani 1 1 d . . . . .
H3A H 1.345(3) 0.4703(15) 0.712(3) 0.072(8) Uiso 1 1 d . . . . .
H3B H 1.291(3) 0.5234(16) 0.813(3) 0.073(8) Uiso 1 1 d . . . . .
O1 O 0.51690(17) 0.39851(10) 0.66467(13) 0.0567(4) 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 0.0033 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'
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
C6 C1 C2 118.76(17) . .
N3 C1 C2 119.98(19) . .
N3 C1 C6 121.22(19) . .
C1 C2 H2 119.9 . .
C3 C2 C1 120.16(17) . .
C3 C2 H2 119.9 . .
C2 C3 H3 119.3 . .
C2 C3 C4 121.31(17) . .
C4 C3 H3 119.3 . .
C3 C4 C7 123.85(16) . .
C5 C4 C3 117.92(17) . .
C5 C4 C7 118.22(16) . .
C4 C5 H5 119.4 . .
C6 C5 C4 121.19(18) . .
C6 C5 H5 119.4 . .
C1 C6 H6 119.7 . .
C5 C6 C1 120.61(17) . .
C5 C6 H6 119.7 . .
N1 C7 C4 115.26(15) . .
O1 C7 C4 122.13(16) . .
O1 C7 N1 122.60(17) . .
C9 C8 C16 117.72(17) . .
N2 C8 C9 125.43(16) . .
N2 C8 C16 116.85(18) . .
C10 C9 C8 118.54(17) . .
C10 C9 C14 119.89(19) . .
C14 C9 C8 121.54(17) . .
C9 C10 H10 119.5 . .
C11 C10 C9 120.9(2) . .
C11 C10 H10 119.5 . .
C10 C11 H11 120.4 . .
C12 C11 C10 119.2(2) . .
C12 C11 H11 120.4 . .
C11 C12 H12 119.6 . .
C11 C12 C13 120.8(2) . .
C13 C12 H12 119.6 . .
C12 C13 H13 119.4 . .
C12 C13 C14 121.2(2) . .
C14 C13 H13 119.4 . .
C9 C14 C15 121.9(2) . .
C13 C14 C9 117.9(2) . .
C13 C14 C15 120.2(2) . .
C14 C15 H15A 109.5 . .
C14 C15 H15B 109.5 . .
C14 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C8 C16 H16A 109.5 . .
C8 C16 H16B 109.5 . .
C8 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C7 N1 H1 120.2 . .
C7 N1 N2 119.67(15) . .
N2 N1 H1 120.2 . .
C8 N2 N1 116.37(15) . .
C1 N3 H3A 114.9(16) . .
C1 N3 H3B 116.4(17) . .
H3A N3 H3B 114(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.391(3) .
C1 C6 1.391(3) .
C1 N3 1.387(3) .
C2 H2 0.9300 .
C2 C3 1.377(3) .
C3 H3 0.9300 .
C3 C4 1.396(2) .
C4 C5 1.385(2) .
C4 C7 1.486(2) .
C5 H5 0.9300 .
C5 C6 1.375(3) .
C6 H6 0.9300 .
C7 N1 1.349(2) .
C7 O1 1.227(2) .
C8 C9 1.492(3) .
C8 C16 1.501(3) .
C8 N2 1.281(2) .
C9 C10 1.394(3) .
C9 C14 1.399(3) .
C10 H10 0.9300 .
C10 C11 1.378(3) .
C11 H11 0.9300 .
C11 C12 1.369(4) .
C12 H12 0.9300 .
C12 C13 1.376(4) .
C13 H13 0.9300 .
C13 C14 1.392(3) .
C14 C15 1.496(3) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 H16A 0.9600 .
C16 H16B 0.9600 .
C16 H16C 0.9600 .
N1 H1 0.8600 .
N1 N2 1.384(2) .
N3 H3A 0.90(3) .
N3 H3B 0.88(3) .
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
C1 C2 C3 C4 -1.0(3) . . . .
C2 C1 C6 C5 -1.5(3) . . . .
C2 C3 C4 C5 -0.9(3) . . . .
C2 C3 C4 C7 -179.34(17) . . . .
C3 C4 C5 C6 1.7(3) . . . .
C3 C4 C7 N1 -27.9(3) . . . .
C3 C4 C7 O1 150.55(19) . . . .
C4 C5 C6 C1 -0.5(3) . . . .
C4 C7 N1 N2 175.84(15) . . . .
C5 C4 C7 N1 153.67(17) . . . .
C5 C4 C7 O1 -27.9(3) . . . .
C6 C1 C2 C3 2.2(3) . . . .
C7 C4 C5 C6 -179.81(18) . . . .
C7 N1 N2 C8 -172.67(17) . . . .
C8 C9 C10 C11 178.97(18) . . . .
C8 C9 C14 C13 -179.20(18) . . . .
C8 C9 C14 C15 3.2(3) . . . .
C9 C8 N2 N1 0.5(3) . . . .
C9 C10 C11 C12 0.7(3) . . . .
C10 C9 C14 C13 2.4(3) . . . .
C10 C9 C14 C15 -175.14(18) . . . .
C10 C11 C12 C13 1.3(4) . . . .
C11 C12 C13 C14 -1.4(4) . . . .
C12 C13 C14 C9 -0.5(3) . . . .
C12 C13 C14 C15 177.2(2) . . . .
C14 C9 C10 C11 -2.6(3) . . . .
C16 C8 C9 C10 63.9(2) . . . .
C16 C8 C9 C14 -114.5(2) . . . .
C16 C8 N2 N1 -178.62(17) . . . .
N2 C8 C9 C10 -115.2(2) . . . .
N2 C8 C9 C14 66.4(3) . . . .
N3 C1 C2 C3 -175.43(18) . . . .
N3 C1 C6 C5 176.13(19) . . . .
O1 C7 N1 N2 -2.6(3) . . . .
