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#$Date: 2022-04-28 12:06:49 +0300 (Thu, 28 Apr 2022) $
#$Revision: 274742 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/50/8105078.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_8105078
loop_
_publ_author_name
'Liu, Jie'
'Cheng, Ruo-Liu'
'Yu, Shu-Zhen'
'Zou, Ying'
_publ_section_title
;
 Crystal structure of (E)-N-[4-(1H)-imidazolyl
 phenyl]-(2-methylphenyl)methanimine, C17H15N3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              267
_journal_page_last               268
_journal_paper_doi               10.1515/ncrs-2019-0584
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C17 H15 N3'
_chemical_formula_sum            'C17 H15 N3'
_chemical_formula_weight         261.32
_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   geom
_cell_angle_alpha                90
_cell_angle_beta                 106.288(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6325(11)
_cell_length_b                   7.8196(7)
_cell_length_c                   15.5644(15)
_cell_measurement_reflns_used    3125
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.39
_cell_measurement_theta_min      2.94
_cell_volume                     1358.9(2)
_computing_cell_refinement       'Bruker SMART [1]'
_computing_data_collection       'Bruker SMART [1]'
_computing_data_reduction        'Bruker SAINT [1]'
_computing_molecular_graphics    'Olex2 [2]'
_computing_publication_material  'Olex2 [2]'
_computing_structure_refinement  'ShelXL [3]'
_computing_structure_solution    'Bruker SHELXTL [3]'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart Apex-CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6669
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.565
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   0.985
_exptl_transmission_factor_min   0.977
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0077(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0363
_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)+(0.0459P)²+0.3298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0975
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             2387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0584_suppl.cif
_cod_data_source_block           123
_cod_database_code               8105078
_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   0.985
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C6(H6), C9(H9), C10(H10), C16(H16), C1(H1), C17(H17), C3(H3),
 C14(H14), C2(H2), C15(H15)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
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 -0.13913(12) 1.28275(19) 0.79809(9) 0.0384(4) Uani 1 1 d . . . . .
H1 H -0.177811 1.180245 0.777804 0.046 Uiso 1 1 calc R . . . .
C2 C -0.09822(14) 1.5472(2) 0.81653(11) 0.0493(4) Uani 1 1 d . . . . .
H2 H -0.104225 1.665477 0.810524 0.059 Uiso 1 1 calc R . . . .
C3 C -0.00469(13) 1.46391(19) 0.87217(10) 0.0450(4) Uani 1 1 d . . . . .
H3 H 0.063336 1.512530 0.910763 0.054 Uiso 1 1 calc R . . . .
C4 C 0.04341(11) 1.15272(16) 0.90036(9) 0.0293(3) Uani 1 1 d . . . . .
C5 C 0.11092(12) 1.16115(18) 0.98916(9) 0.0330(3) Uani 1 1 d . . . . .
H5 H 0.107952 1.258473 1.022821 0.040 Uiso 1 1 calc R . . . .
C6 C 0.18282(11) 1.02448(18) 1.02774(9) 0.0343(3) Uani 1 1 d . . . . .
H6 H 0.228249 1.030602 1.087251 0.041 Uiso 1 1 calc R . . . .
C7 C 0.18744(11) 0.87804(17) 0.97792(9) 0.0309(3) Uani 1 1 d . . . . .
C8 C 0.11752(12) 0.87102(17) 0.88939(9) 0.0334(3) Uani 1 1 d . . . . .
H8 H 0.118480 0.772747 0.855944 0.040 Uiso 1 1 calc R . . . .
C9 C 0.04690(12) 1.00715(17) 0.85045(9) 0.0325(3) Uani 1 1 d . . . . .
H9 H 0.001727 1.001373 0.790866 0.039 Uiso 1 1 calc R . . . .
C10 C 0.36448(12) 0.75367(19) 1.05933(9) 0.0374(4) Uani 1 1 d . . . . .
H10 H 0.392569 0.864889 1.071686 0.045 Uiso 1 1 calc R . . . .
C11 C 0.44638(12) 0.61137(18) 1.09508(9) 0.0346(3) Uani 1 1 d . . . . .
C12 C 0.57051(12) 0.6397(2) 1.12655(9) 0.0388(4) Uani 1 1 d . . . . .
C13 C 0.62447(15) 0.8161(2) 1.12955(13) 0.0593(5) Uani 1 1 d . . . . .
H13A H 0.710010 0.808487 1.152361 0.089 Uiso 1 1 calc GR . . . .
H13B H 0.593852 0.888382 1.167886 0.089 Uiso 1 1 calc GR . . . .
H13C H 0.603829 0.863533 1.070289 0.089 Uiso 1 1 calc GR . . . .
C14 C 0.64442(13) 0.4989(2) 1.15422(10) 0.0465(4) Uani 1 1 d . . . . .
H14 H 0.726794 0.515302 1.174712 0.056 Uiso 1 1 calc R . . . .
C15 C 0.59926(15) 0.3357(2) 1.15218(10) 0.0493(4) Uani 1 1 d . . . . .
H15 H 0.650961 0.243722 1.170852 0.059 Uiso 1 1 calc R . . . .
C16 C 0.47750(15) 0.3086(2) 1.12249(10) 0.0477(4) Uani 1 1 d . . . . .
H16 H 0.446487 0.198868 1.121909 0.057 Uiso 1 1 calc R . . . .
C17 C 0.40200(13) 0.44575(19) 1.09363(10) 0.0418(4) Uani 1 1 d . . . . .
H17 H 0.319882 0.427227 1.072803 0.050 Uiso 1 1 calc R . . . .
N1 N -0.03077(9) 1.29295(14) 0.86002(7) 0.0322(3) Uani 1 1 d . . . . .
N2 N -0.18314(11) 1.43363(16) 0.77008(8) 0.0452(3) Uani 1 1 d . . . . .
N3 N 0.25739(10) 0.73184(15) 1.01247(8) 0.0371(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 0.0033 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'
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
C10 N3 C7 118.47(12) . .
C1 N1 C4 126.42(12) . .
C1 N1 C3 106.29(11) . .
C3 N1 C4 127.21(11) . .
C5 C4 N1 120.37(12) . .
C9 C4 N1 119.59(11) . .
C9 C4 C5 120.04(12) . .
C7 C8 H8 119.5 . .
C9 C8 H8 119.5 . .
C9 C8 C7 121.09(13) . .
C8 C7 N3 117.23(12) . .
C8 C7 C6 118.75(12) . .
C6 C7 N3 124.00(12) . .
C4 C5 H5 120.0 . .
C6 C5 C4 119.97(13) . .
C6 C5 H5 120.0 . .
C7 C6 H6 119.8 . .
C5 C6 C7 120.38(12) . .
C5 C6 H6 119.8 . .
C4 C9 H9 120.1 . .
C8 C9 C4 119.75(12) . .
C8 C9 H9 120.1 . .
N3 C10 H10 118.5 . .
N3 C10 C11 123.01(13) . .
C11 C10 H10 118.5 . .
C1 N2 C2 104.53(12) . .
C17 C16 H16 120.3 . .
C15 C16 H16 120.3 . .
C15 C16 C17 119.40(15) . .
C12 C11 C10 120.40(13) . .
C17 C11 C10 120.03(13) . .
C17 C11 C12 119.48(13) . .
N1 C1 H1 123.8 . .
N2 C1 N1 112.42(13) . .
N2 C1 H1 123.8 . .
C11 C12 C13 122.13(13) . .
C14 C12 C11 117.96(14) . .
C14 C12 C13 119.91(14) . .
C16 C17 C11 121.25(14) . .
C16 C17 H17 119.4 . .
C11 C17 H17 119.4 . .
N1 C3 H3 127.0 . .
C2 C3 N1 105.90(13) . .
C2 C3 H3 127.0 . .
C12 C14 H14 119.0 . .
C15 C14 C12 121.91(14) . .
C15 C14 H14 119.0 . .
N2 C2 H2 124.6 . .
C3 C2 N2 110.86(13) . .
C3 C2 H2 124.6 . .
C16 C15 H15 120.0 . .
C14 C15 C16 119.98(14) . .
C14 C15 H15 120.0 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 C7 1.4188(17) .
N3 C10 1.2661(18) .
N1 C4 1.4273(16) .
N1 C1 1.3575(17) .
N1 C3 1.3721(18) .
C4 C5 1.3866(18) .
C4 C9 1.3852(18) .
C8 H8 0.9300 .
C8 C7 1.3908(19) .
C8 C9 1.3769(18) .
C7 C6 1.3924(19) .
C5 H5 0.9300 .
C5 C6 1.3858(19) .
C6 H6 0.9300 .
C9 H9 0.9300 .
C10 H10 0.9300 .
C10 C11 1.4690(19) .
N2 C1 1.3111(18) .
N2 C2 1.374(2) .
C16 H16 0.9300 .
C16 C17 1.379(2) .
C16 C15 1.377(2) .
C11 C12 1.406(2) .
C11 C17 1.392(2) .
C1 H1 0.9300 .
C12 C14 1.389(2) .
C12 C13 1.511(2) .
C17 H17 0.9300 .
C3 H3 0.9300 .
C3 C2 1.353(2) .
C14 H14 0.9300 .
C14 C15 1.377(2) .
C2 H2 0.9300 .
C15 H15 0.9300 .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
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
N3 C7 C6 C5 -179.20(12) . . . .
N3 C10 C11 C12 163.77(14) . . . .
N3 C10 C11 C17 -12.8(2) . . . .
N1 C4 C5 C6 -179.91(12) . . . .
N1 C4 C9 C8 -179.41(12) . . . .
N1 C3 C2 N2 0.50(19) . . . .
C4 N1 C1 N2 -176.71(12) . . . .
C4 N1 C3 C2 176.47(13) . . . .
C4 C5 C6 C7 -0.2(2) . . . .
C8 C7 C6 C5 -0.8(2) . . . .
C7 N3 C10 C11 -177.25(12) . . . .
C7 C8 C9 C4 -1.2(2) . . . .
C5 C4 C9 C8 0.06(19) . . . .
C9 C4 C5 C6 0.6(2) . . . .
C9 C8 C7 N3 -179.99(12) . . . .
C9 C8 C7 C6 1.5(2) . . . .
C10 N3 C7 C8 136.33(14) . . . .
C10 N3 C7 C6 -45.27(19) . . . .
C10 C11 C12 C14 -175.90(13) . . . .
C10 C11 C12 C13 3.1(2) . . . .
C10 C11 C17 C16 176.64(14) . . . .
C11 C12 C14 C15 -0.6(2) . . . .
C1 N1 C4 C5 -144.32(14) . . . .
C1 N1 C4 C9 35.2(2) . . . .
C1 N1 C3 C2 -0.43(18) . . . .
C1 N2 C2 C3 -0.37(19) . . . .
C12 C11 C17 C16 0.0(2) . . . .
C12 C14 C15 C16 -0.3(2) . . . .
C17 C16 C15 C14 1.1(2) . . . .
C17 C11 C12 C14 0.7(2) . . . .
C17 C11 C12 C13 179.76(15) . . . .
C3 N1 C4 C5 39.4(2) . . . .
C3 N1 C4 C9 -141.14(15) . . . .
C3 N1 C1 N2 0.22(18) . . . .
C2 N2 C1 N1 0.08(18) . . . .
C15 C16 C17 C11 -0.9(2) . . . .
C13 C12 C14 C15 -179.63(15) . . . .
