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#$Date: 2022-08-24 12:03:29 +0300 (Wed, 24 Aug 2022) $
#$Revision: 277379 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105695.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_8105695
loop_
_publ_author_name
'Zheng, Bin-Yu'
'Sun, Na-Bo'
'Chen, Xue-Song'
'Liu, Xing-Hai'
_publ_section_title
;
 The crystal structure of
 (E)-3-chloro-2-(2-(4-fluorobenzylidene)hydrazinyl)pyridine, C12H9ClFN3
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              355
_journal_page_last               356
_journal_paper_doi               10.1515/ncrs-2021-0489
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C12 H9 Cl F N3'
_chemical_formula_sum            'C12 H9 Cl F N3'
_chemical_formula_weight         249.67
_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   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 91.744(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.120(4)
_cell_length_b                   13.823(6)
_cell_length_c                   16.480(7)
_cell_measurement_reflns_used    22536
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      27.846
_cell_measurement_theta_min      1.932
_cell_volume                     2304.3(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22536
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.846
_diffrn_reflns_theta_min         1.923
_exptl_absorpt_coefficient_mu    0.324
_exptl_absorpt_correction_T_max  0.9441
_exptl_absorpt_correction_T_min  0.9092
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4604
_reflns_number_total             5483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0489_suppl.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        2304.4(17)
_cod_database_code               8105695
_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   0.938
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
  N5(H5A), C14(H14), C15(H15), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23),
  C24(H24)
;
_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
Cl1 Cl -0.38845(4) -0.19073(3) 0.08628(3) 0.03236(12) Uani 1 1 d . . . . .
F1 F 0.20724(9) 0.40525(6) 0.24092(6) 0.0338(2) Uani 1 1 d . . . . .
N1 N -0.22853(13) 0.08362(8) 0.17193(8) 0.0222(3) Uani 1 1 d . . . . .
N2 N -0.29329(13) -0.00277(8) 0.15728(8) 0.0245(3) Uani 1 1 d . . . . .
H2 H -0.2525 -0.0582 0.1662 0.029 Uiso 1 1 calc R . . . .
N3 N -0.49118(13) 0.08102(8) 0.13412(8) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.12947(15) 0.32514(10) 0.23167(10) 0.0234(3) Uani 1 1 d . . . . .
C2 C -0.00248(16) 0.33696(11) 0.21119(11) 0.0279(4) Uani 1 1 d . . . . .
H2A H -0.0389 0.3998 0.2036 0.033 Uiso 1 1 calc R . . . .
C3 C -0.08082(15) 0.25556(10) 0.20191(10) 0.0261(4) Uani 1 1 d . . . . .
H3 H -0.1722 0.2627 0.1882 0.031 Uiso 1 1 calc R . . . .
C4 C -0.02774(14) 0.16277(10) 0.21239(9) 0.0198(3) Uani 1 1 d . . . . .
C5 C 0.10637(15) 0.15427(11) 0.23368(10) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.1440 0.0919 0.2415 0.030 Uiso 1 1 calc R . . . .
C6 C 0.18574(15) 0.23591(11) 0.24358(10) 0.0281(4) Uani 1 1 d . . . . .
H6 H 0.2769 0.2299 0.2583 0.034 Uiso 1 1 calc R . . . .
C7 C -0.10802(15) 0.07601(10) 0.19870(10) 0.0221(3) Uani 1 1 d . . . . .
H7 H -0.0713 0.0139 0.2096 0.026 Uiso 1 1 calc R . . . .
C8 C -0.42223(15) -0.00121(10) 0.12863(9) 0.0210(3) Uani 1 1 d . . . . .
C9 C -0.48146(16) -0.08549(10) 0.09531(10) 0.0243(3) Uani 1 1 d . . . . .
C10 C -0.61163(16) -0.08396(11) 0.06917(10) 0.0291(4) Uani 1 1 d . . . . .
H10 H -0.6525 -0.1405 0.0474 0.035 Uiso 1 1 calc R . . . .
C11 C -0.68249(16) 0.00173(11) 0.07515(10) 0.0303(4) Uani 1 1 d . . . . .
H11 H -0.7727 0.0053 0.0577 0.036 Uiso 1 1 calc R . . . .
C12 C -0.61782(16) 0.08122(11) 0.10706(10) 0.0274(4) Uani 1 1 d . . . . .
H12 H -0.6658 0.1401 0.1102 0.033 Uiso 1 1 calc R . . . .
Cl2 Cl 0.05702(4) 0.58235(2) 0.16911(2) 0.02695(11) Uani 1 1 d . . . . .
F2 F -0.23767(11) 1.13806(7) 0.56619(6) 0.0448(3) Uani 1 1 d . . . . .
N4 N -0.09219(12) 0.83511(8) 0.29660(8) 0.0208(3) Uani 1 1 d . . . . .
N5 N -0.05299(12) 0.75652(8) 0.25234(8) 0.0219(3) Uani 1 1 d . . . . .
H5A H -0.0418 0.6997 0.2756 0.026 Uiso 1 1 calc R . . . .
N6 N -0.06113(13) 0.85439(8) 0.13699(8) 0.0257(3) Uani 1 1 d . . . . .
C13 C -0.20850(16) 1.05980(11) 0.51954(11) 0.0288(4) Uani 1 1 d . . . . .
C14 C -0.23277(15) 1.06506(11) 0.43733(11) 0.0275(4) Uani 1 1 d . . . . .
H14 H -0.2710 1.1216 0.4137 0.033 Uiso 1 1 calc R . . . .
C15 C -0.20081(14) 0.98696(10) 0.38954(10) 0.0236(3) Uani 1 1 d . . . . .
H15 H -0.2186 0.9893 0.3326 0.028 Uiso 1 1 calc R . . . .
C16 C -0.14204(14) 0.90391(10) 0.42449(10) 0.0212(3) Uani 1 1 d . . . . .
C17 C -0.12203(15) 0.90098(10) 0.50860(10) 0.0248(3) Uani 1 1 d . . . . .
H17 H -0.0854 0.8445 0.5332 0.030 Uiso 1 1 calc R . . . .
C18 C -0.15470(15) 0.97917(11) 0.55715(10) 0.0281(4) Uani 1 1 d . . . . .
H18 H -0.1404 0.9771 0.6144 0.034 Uiso 1 1 calc R . . . .
C19 C -0.09868(15) 0.82341(10) 0.37355(10) 0.0222(3) Uani 1 1 d . . . . .
H19 H -0.0756 0.7630 0.3975 0.027 Uiso 1 1 calc R . . . .
C20 C -0.03169(14) 0.76864(10) 0.17111(10) 0.0205(3) Uani 1 1 d . . . . .
C21 C 0.02210(14) 0.69337(10) 0.12411(10) 0.0219(3) Uani 1 1 d . . . . .
C22 C 0.04700(16) 0.70789(12) 0.04390(10) 0.0307(4) Uani 1 1 d . . . . .
H22 H 0.0824 0.6573 0.0121 0.037 Uiso 1 1 calc R . . . .
C23 C 0.01954(19) 0.79819(12) 0.00960(11) 0.0384(4) Uani 1 1 d . . . . .
H23 H 0.0375 0.8116 -0.0455 0.046 Uiso 1 1 calc R . . . .
C24 C -0.03450(17) 0.86693(12) 0.05883(11) 0.0344(4) Uani 1 1 d . . . . .
H24 H -0.0545 0.9282 0.0354 0.041 Uiso 1 1 calc R . . . .
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'
F F 0.0171 0.0103 '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'
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
C7 N1 N2 115.39(12) . .
C8 N2 N1 119.18(11) . .
C8 N3 C12 118.24(13) . .
F1 C1 C2 118.87(13) . .
F1 C1 C6 118.61(14) . .
C6 C1 C2 122.52(14) . .
C1 C2 C3 118.63(14) . .
C2 C3 C4 121.05(14) . .
C3 C4 C7 121.55(14) . .
C5 C4 C3 118.34(13) . .
C5 C4 C7 120.06(13) . .
C6 C5 C4 120.95(14) . .
C1 C6 C5 118.50(15) . .
N1 C7 C4 120.10(13) . .
N2 C8 C9 120.50(13) . .
N3 C8 N2 118.79(13) . .
N3 C8 C9 120.70(14) . .
C8 C9 Cl1 119.85(12) . .
C10 C9 Cl1 120.12(12) . .
C10 C9 C8 120.03(14) . .
C9 C10 C11 118.88(14) . .
C12 C11 C10 117.87(15) . .
N3 C12 C11 124.27(14) . .
C19 N4 N5 116.73(12) . .
C20 N5 N4 118.54(12) . .
C24 N6 C20 118.05(13) . .
F2 C13 C14 118.63(15) . .
F2 C13 C18 118.46(16) . .
C14 C13 C18 122.91(15) . .
C13 C14 C15 118.95(15) . .
C14 C15 C16 120.50(15) . .
C15 C16 C19 120.91(15) . .
C17 C16 C15 118.48(14) . .
C17 C16 C19 120.59(14) . .
C18 C17 C16 121.28(14) . .
C13 C18 C17 117.84(16) . .
N4 C19 C16 119.66(13) . .
N5 C20 C21 121.21(13) . .
N6 C20 N5 118.50(13) . .
N6 C20 C21 120.28(14) . .
C20 C21 Cl2 119.52(12) . .
C22 C21 Cl2 120.08(12) . .
C22 C21 C20 120.40(14) . .
C21 C22 C23 118.85(15) . .
C24 C23 C22 117.23(16) . .
N6 C24 C23 125.14(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C9 1.7416(16) .
F1 C1 1.3644(16) .
N1 N2 1.3799(16) .
N1 C7 1.289(2) .
N2 C8 1.374(2) .
N3 C8 1.3382(18) .
N3 C12 1.344(2) .
C1 C2 1.377(2) .
C1 C6 1.370(2) .
C2 C3 1.382(2) .
C3 C4 1.399(2) .
C4 C5 1.396(2) .
C4 C7 1.462(2) .
C5 C6 1.392(2) .
C8 C9 1.414(2) .
C9 C10 1.374(2) .
C10 C11 1.390(2) .
C11 C12 1.375(2) .
Cl2 C21 1.7362(16) .
F2 C13 1.3647(18) .
N4 N5 1.3737(17) .
N4 C19 1.282(2) .
N5 C20 1.373(2) .
N6 C20 1.3416(19) .
N6 C24 1.335(2) .
C13 C14 1.371(2) .
C13 C18 1.379(2) .
C14 C15 1.381(2) .
C15 C16 1.408(2) .
C16 C17 1.395(2) .
C16 C19 1.469(2) .
C17 C18 1.391(2) .
C20 C21 1.416(2) .
C21 C22 1.368(2) .
C22 C23 1.395(2) .
C23 C24 1.374(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
Cl1 C9 C10 C11 -178.32(12) . . . .
F1 C1 C2 C3 -179.99(14) . . . .
F1 C1 C6 C5 -179.66(14) . . . .
N1 N2 C8 N3 -15.9(2) . . . .
N1 N2 C8 C9 165.18(14) . . . .
N2 N1 C7 C4 176.88(13) . . . .
N2 C8 C9 Cl1 -2.9(2) . . . .
N2 C8 C9 C10 177.97(14) . . . .
N3 C8 C9 Cl1 178.27(11) . . . .
N3 C8 C9 C10 -0.9(2) . . . .
C1 C2 C3 C4 -0.5(2) . . . .
C2 C1 C6 C5 0.7(2) . . . .
C2 C3 C4 C5 0.9(2) . . . .
C2 C3 C4 C7 -176.83(15) . . . .
C3 C4 C5 C6 -0.5(2) . . . .
C3 C4 C7 N1 4.0(2) . . . .
C4 C5 C6 C1 -0.2(2) . . . .
C5 C4 C7 N1 -173.68(14) . . . .
C6 C1 C2 C3 -0.3(3) . . . .
C7 N1 N2 C8 179.99(14) . . . .
C7 C4 C5 C6 177.23(14) . . . .
C8 N3 C12 C11 1.1(2) . . . .
C8 C9 C10 C11 0.9(2) . . . .
C9 C10 C11 C12 0.1(2) . . . .
C10 C11 C12 N3 -1.2(3) . . . .
C12 N3 C8 N2 -178.97(14) . . . .
C12 N3 C8 C9 -0.1(2) . . . .
Cl2 C21 C22 C23 -179.19(13) . . . .
F2 C13 C14 C15 178.59(14) . . . .
F2 C13 C18 C17 -178.24(13) . . . .
N4 N5 C20 N6 -5.7(2) . . . .
N4 N5 C20 C21 173.24(13) . . . .
N5 N4 C19 C16 -178.97(12) . . . .
N5 C20 C21 Cl2 2.1(2) . . . .
N5 C20 C21 C22 -177.68(14) . . . .
N6 C20 C21 Cl2 -178.98(11) . . . .
N6 C20 C21 C22 1.3(2) . . . .
C13 C14 C15 C16 -1.1(2) . . . .
C14 C13 C18 C17 1.1(2) . . . .
C14 C15 C16 C17 2.6(2) . . . .
C14 C15 C16 C19 -175.43(14) . . . .
C15 C16 C17 C18 -2.2(2) . . . .
C15 C16 C19 N4 12.5(2) . . . .
C16 C17 C18 C13 0.4(2) . . . .
C17 C16 C19 N4 -165.49(14) . . . .
C18 C13 C14 C15 -0.8(2) . . . .
C19 N4 N5 C20 -173.43(13) . . . .
C19 C16 C17 C18 175.79(14) . . . .
C20 N6 C24 C23 0.9(3) . . . .
C20 C21 C22 C23 0.5(2) . . . .
C21 C22 C23 C24 -1.6(3) . . . .
C22 C23 C24 N6 0.9(3) . . . .
C24 N6 C20 N5 177.03(14) . . . .
C24 N6 C20 C21 -2.0(2) . . . .
