#------------------------------------------------------------------------------
#$Date: 2022-11-24 12:09:55 +0200 (Thu, 24 Nov 2022) $
#$Revision: 279545 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106246.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_8106246
loop_
_publ_author_name
'Alotaibi, Mohammad Hayal'
_publ_section_title
;
 Crystal structure of
 (E)-N′-(4-methoxybenzylidene)-5-methyl-1-(4-tolyl)-1H-1,2,3-triazole-4-carbohydrazide,
 C19H19N5O2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              649
_journal_page_last               650
_journal_paper_doi               10.1515/ncrs-2017-0421
_journal_volume                  233
_journal_year                    2018
_chemical_formula_sum            'C19 H19 N5 O2'
_chemical_formula_weight         349.39
_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                102.751(2)
_cell_angle_beta                 96.130(2)
_cell_angle_gamma                103.079(2)
_cell_formula_units_Z            2
_cell_length_a                   6.6320(3)
_cell_length_b                   10.3272(5)
_cell_length_c                   13.0832(6)
_cell_measurement_reflns_used    5998
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.08
_cell_measurement_theta_min      2.30
_cell_volume                     839.63(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10420
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.093
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.183
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0553
_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)+(0.0757P)²+0.2060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1521
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2273
_reflns_number_total             2930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0421_suppl.cif
_cod_data_source_block           a_a
_cod_database_code               8106246
_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.
;
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
O1 O 0.6563(2) 0.38424(16) 0.31037(12) 0.0265(4) Uani 1 1 d . . . . .
O2 O -0.1820(2) 0.01614(16) 0.67980(11) 0.0216(4) Uani 1 1 d . . . . .
N1 N 0.7157(3) 0.67425(18) 0.12365(13) 0.0167(4) Uani 1 1 d . . . . .
N2 N 0.5427(3) 0.7158(2) 0.15081(14) 0.0236(5) Uani 1 1 d . . . . .
N3 N 0.4659(3) 0.64357(19) 0.21453(14) 0.0220(5) Uani 1 1 d . . . . .
N4 N 0.3692(3) 0.46333(19) 0.34138(14) 0.0200(4) Uani 1 1 d . . . . .
N5 N 0.3087(3) 0.37662(18) 0.40517(13) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.8333(3) 0.7349(2) 0.05278(15) 0.0169(5) Uani 1 1 d . . . . .
C2 C 1.0494(3) 0.7823(2) 0.07805(16) 0.0191(5) Uani 1 1 d . . . . .
H2A H 1.1204 0.7761 0.1431 0.023 Uiso 1 1 calc R U . . .
C3 C 1.1613(3) 0.8386(2) 0.00830(17) 0.0208(5) Uani 1 1 d . . . . .
H3A H 1.3097 0.8712 0.0262 0.025 Uiso 1 1 calc R U . . .
C4 C 1.0608(3) 0.8486(2) -0.08818(16) 0.0198(5) Uani 1 1 d . . . . .
C5 C 0.8428(4) 0.8018(2) -0.11091(16) 0.0215(5) Uani 1 1 d . . . . .
H5A H 0.7709 0.8094 -0.1753 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7285(3) 0.7445(2) -0.04213(16) 0.0205(5) Uani 1 1 d . . . . .
H6A H 0.5800 0.7120 -0.0595 0.025 Uiso 1 1 calc R U . . .
C7 C 1.1835(4) 0.9045(3) -0.16557(18) 0.0282(6) Uani 1 1 d . . . . .
H7A H 1.2999 0.9829 -0.1269 0.042 Uiso 1 1 calc R U . . .
H7B H 1.0916 0.9345 -0.2142 0.042 Uiso 1 1 calc R U . . .
H7C H 1.2391 0.8328 -0.2063 0.042 Uiso 1 1 calc R U . . .
C8 C 0.9204(4) 0.5055(2) 0.15524(18) 0.0268(6) Uani 1 1 d . . . . .
H8A H 0.8927 0.4233 0.1827 0.040 Uiso 1 1 calc R U . . .
H8B H 1.0547 0.5681 0.1930 0.040 Uiso 1 1 calc R U . . .
H8C H 0.9264 0.4787 0.0792 0.040 Uiso 1 1 calc R U . . .
C9 C 0.7493(3) 0.5756(2) 0.17167(15) 0.0168(5) Uani 1 1 d . . . . .
C10 C 0.5884(3) 0.5571(2) 0.22933(15) 0.0166(5) Uani 1 1 d . . . . .
C11 C 0.5441(3) 0.4606(2) 0.29713(16) 0.0190(5) Uani 1 1 d . . . . .
C12 C 0.1246(3) 0.3688(2) 0.42921(16) 0.0207(5) Uani 1 1 d . . . . .
H12A H 0.0392 0.4199 0.4019 0.025 Uiso 1 1 calc R U . . .
C13 C 0.0448(3) 0.2825(2) 0.49789(16) 0.0182(5) Uani 1 1 d . . . . .
C14 C 0.1714(3) 0.2124(2) 0.54576(16) 0.0192(5) Uani 1 1 d . . . . .
H14A H 0.3135 0.2244 0.5355 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0933(3) 0.1277(2) 0.60651(16) 0.0199(5) Uani 1 1 d . . . . .
H15A H 0.1813 0.0815 0.6381 0.024 Uiso 1 1 calc R U . . .
C16 C -0.1153(3) 0.1083(2) 0.62275(15) 0.0179(5) Uani 1 1 d . . . . .
C17 C -0.2414(3) 0.1802(2) 0.57919(16) 0.0194(5) Uani 1 1 d . . . . .
H17A H -0.3815 0.1711 0.5922 0.023 Uiso 1 1 calc R U . . .
C18 C -0.1604(3) 0.2653(2) 0.51645(16) 0.0211(5) Uani 1 1 d . . . . .
H18A H -0.2476 0.3128 0.4856 0.025 Uiso 1 1 calc R U . . .
C19 C -0.4003(3) -0.0186(2) 0.68669(18) 0.0248(5) Uani 1 1 d . . . . .
H19A H -0.4329 -0.0986 0.7164 0.037 Uiso 1 1 calc R U . . .
H19B H -0.4832 -0.0403 0.6156 0.037 Uiso 1 1 calc R U . . .
H19C H -0.4345 0.0593 0.7328 0.037 Uiso 1 1 calc R U . . .
H1N4 H 0.287(4) 0.517(3) 0.324(2) 0.041(8) Uiso 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
C16 O2 C19 117.55(16) . .
C9 N1 N2 111.05(16) . .
C9 N1 C1 129.13(17) . .
N2 N1 C1 119.82(16) . .
N3 N2 N1 106.88(16) . .
N2 N3 C10 109.05(16) . .
C11 N4 N5 119.87(18) . .
C11 N4 H1N4 119.6(16) . .
N5 N4 H1N4 120.3(16) . .
C12 N5 N4 115.82(18) . .
C2 C1 C6 120.35(19) . .
C2 C1 N1 120.22(18) . .
C6 C1 N1 119.42(19) . .
C3 C2 C1 119.69(19) . .
C3 C2 H2A 120.2 . .
C1 C2 H2A 120.2 . .
C2 C3 C4 121.4(2) . .
C2 C3 H3A 119.3 . .
C4 C3 H3A 119.3 . .
C5 C4 C3 117.68(19) . .
C5 C4 C7 121.09(19) . .
C3 C4 C7 121.2(2) . .
C6 C5 C4 121.63(19) . .
C6 C5 H5A 119.2 . .
C4 C5 H5A 119.2 . .
C5 C6 C1 119.3(2) . .
C5 C6 H6A 120.4 . .
C1 C6 H6A 120.4 . .
C4 C7 H7A 109.5 . .
C4 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C4 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 H8A 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C9 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N1 C9 C10 103.84(18) . .
N1 C9 C8 124.23(18) . .
C10 C9 C8 131.9(2) . .
N3 C10 C9 109.18(18) . .
N3 C10 C11 122.82(18) . .
C9 C10 C11 128.00(18) . .
O1 C11 N4 123.7(2) . .
O1 C11 C10 122.18(18) . .
N4 C11 C10 114.14(18) . .
N5 C12 C13 120.9(2) . .
N5 C12 H12A 119.6 . .
C13 C12 H12A 119.6 . .
C18 C13 C14 118.1(2) . .
C18 C13 C12 120.60(19) . .
C14 C13 C12 121.33(19) . .
C15 C14 C13 121.01(19) . .
C15 C14 H14A 119.5 . .
C13 C14 H14A 119.5 . .
C14 C15 C16 120.6(2) . .
C14 C15 H15A 119.7 . .
C16 C15 H15A 119.7 . .
O2 C16 C17 124.37(19) . .
O2 C16 C15 116.24(18) . .
C17 C16 C15 119.4(2) . .
C18 C17 C16 119.45(19) . .
C18 C17 H17A 120.3 . .
C16 C17 H17A 120.3 . .
C13 C18 C17 121.5(2) . .
C13 C18 H18A 119.3 . .
C17 C18 H18A 119.3 . .
O2 C19 H19A 109.5 . .
O2 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O2 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.226(2) .
O2 C16 1.361(2) .
O2 C19 1.428(3) .
N1 C9 1.355(3) .
N1 N2 1.367(2) .
N1 C1 1.432(3) .
N2 N3 1.305(2) .
N3 C10 1.366(3) .
N4 C11 1.354(3) .
N4 N5 1.378(2) .
N4 H1N4 0.90(3) .
N5 C12 1.282(3) .
C1 C2 1.383(3) .
C1 C6 1.391(3) .
C2 C3 1.381(3) .
C2 H2A 0.9500 .
C3 C4 1.399(3) .
C3 H3A 0.9500 .
C4 C5 1.394(3) .
C4 C7 1.497(3) .
C5 C6 1.383(3) .
C5 H5A 0.9500 .
C6 H6A 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C9 1.488(3) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.374(3) .
C10 C11 1.476(3) .
C12 C13 1.457(3) .
C12 H12A 0.9500 .
C13 C18 1.387(3) .
C13 C14 1.409(3) .
C14 C15 1.362(3) .
C14 H14A 0.9500 .
C15 C16 1.398(3) .
C15 H15A 0.9500 .
C16 C17 1.393(3) .
C17 C18 1.391(3) .
C17 H17A 0.9500 .
C18 H18A 0.9500 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
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
C9 N1 N2 N3 -0.6(2) . . . .
C1 N1 N2 N3 179.37(17) . . . .
N1 N2 N3 C10 0.5(2) . . . .
C11 N4 N5 C12 -168.70(19) . . . .
C9 N1 C1 C2 -48.6(3) . . . .
N2 N1 C1 C2 131.5(2) . . . .
C9 N1 C1 C6 130.8(2) . . . .
N2 N1 C1 C6 -49.1(3) . . . .
C6 C1 C2 C3 -0.4(3) . . . .
N1 C1 C2 C3 178.98(18) . . . .
C1 C2 C3 C4 -0.2(3) . . . .
C2 C3 C4 C5 1.0(3) . . . .
C2 C3 C4 C7 -177.50(19) . . . .
C3 C4 C5 C6 -1.3(3) . . . .
C7 C4 C5 C6 177.17(19) . . . .
C4 C5 C6 C1 0.8(3) . . . .
C2 C1 C6 C5 0.0(3) . . . .
N1 C1 C6 C5 -179.31(18) . . . .
N2 N1 C9 C10 0.4(2) . . . .
C1 N1 C9 C10 -179.55(19) . . . .
N2 N1 C9 C8 177.6(2) . . . .
C1 N1 C9 C8 -2.3(3) . . . .
N2 N3 C10 C9 -0.3(2) . . . .
N2 N3 C10 C11 -179.80(19) . . . .
N1 C9 C10 N3 -0.1(2) . . . .
C8 C9 C10 N3 -177.0(2) . . . .
N1 C9 C10 C11 179.4(2) . . . .
C8 C9 C10 C11 2.5(4) . . . .
N5 N4 C11 O1 -0.1(3) . . . .
N5 N4 C11 C10 179.03(17) . . . .
N3 C10 C11 O1 -179.5(2) . . . .
C9 C10 C11 O1 1.1(4) . . . .
N3 C10 C11 N4 1.4(3) . . . .
C9 C10 C11 N4 -178.0(2) . . . .
N4 N5 C12 C13 -178.80(17) . . . .
N5 C12 C13 C18 -174.6(2) . . . .
N5 C12 C13 C14 4.3(3) . . . .
C18 C13 C14 C15 1.5(3) . . . .
C12 C13 C14 C15 -177.4(2) . . . .
C13 C14 C15 C16 0.1(3) . . . .
C19 O2 C16 C17 6.2(3) . . . .
C19 O2 C16 C15 -172.48(18) . . . .
C14 C15 C16 O2 176.56(18) . . . .
C14 C15 C16 C17 -2.2(3) . . . .
O2 C16 C17 C18 -175.86(18) . . . .
C15 C16 C17 C18 2.8(3) . . . .
C14 C13 C18 C17 -0.9(3) . . . .
C12 C13 C18 C17 178.05(19) . . . .
C16 C17 C18 C13 -1.3(3) . . . .
