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#$Date: 2022-10-21 12:35:58 +0300 (Fri, 21 Oct 2022) $
#$Revision: 278712 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105945.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_8105945
loop_
_publ_author_name
'Luo, Xiao-Li'
'Yang, Tao'
_publ_section_title
;
 The crystal structure of N 1,N
 4-bis(pyridin-3-yl)cyclohexane-1,4-dicarboxamide, C18H20N4O2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1087
_journal_page_last               1089
_journal_paper_doi               10.1515/ncrs-2019-0284
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C18 H20 N4 O2'
_chemical_formula_sum            'C18 H20 N4 O2'
_chemical_formula_weight         324.38
_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                 105.508(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8951(5)
_cell_length_b                   9.9303(7)
_cell_length_c                   10.5446(7)
_cell_measurement_reflns_used    1444
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      62.4127
_cell_measurement_theta_min      4.3473
_cell_volume                     796.61(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4346
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        62.502
_diffrn_reflns_theta_max         62.502
_diffrn_reflns_theta_min         6.232
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        -
_diffrn_standards_interval_count -
_diffrn_standards_interval_time  -
_diffrn_standards_number         -
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       Block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0357
_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)+(0.0573P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0923
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                952
_reflns_number_total             1267
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0284_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105945
_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   0.832
_shelx_estimated_absorpt_t_max   0.879
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
O1 O 0.14835(16) 0.18255(14) -0.19183(10) 0.0674(4) Uani 1 1 d . . . . .
N1 N -0.31259(17) 0.37119(16) -0.21136(12) 0.0535(4) Uani 1 1 d . . . . .
N2 N 0.06511(16) 0.18672(13) -0.00251(11) 0.0460(4) Uani 1 1 d . . . . .
H2 H 0.084596 0.153198 0.075267 0.055 Uiso 1 1 calc R U . . .
C1 C -0.3464(2) 0.45528(17) -0.12225(17) 0.0519(5) Uani 1 1 d . . . . .
H1 H -0.437685 0.516936 -0.149141 0.062 Uiso 1 1 calc R U . . .
C2 C -0.2514(2) 0.45408(17) 0.00779(17) 0.0546(5) Uani 1 1 d . . . . .
H2A H -0.279704 0.513040 0.067538 0.066 Uiso 1 1 calc R U . . .
C3 C -0.1146(2) 0.36523(17) 0.04861(15) 0.0497(4) Uani 1 1 d . . . . .
H3 H -0.049480 0.363279 0.136257 0.060 Uiso 1 1 calc R U . . .
C4 C -0.07457(19) 0.27862(15) -0.04186(14) 0.0412(4) Uani 1 1 d . . . . .
C5 C -0.1802(2) 0.28472(17) -0.17069(15) 0.0505(4) Uani 1 1 d . . . . .
H5 H -0.157053 0.224957 -0.231862 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1718(2) 0.14651(16) -0.07727(15) 0.0445(4) Uani 1 1 d . . . . .
C7 C 0.3246(2) 0.05826(15) -0.00967(14) 0.0425(4) Uani 1 1 d . . . . .
H7 H 0.301362 0.020221 0.069783 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4926(2) 0.14268(16) 0.03078(15) 0.0472(4) Uani 1 1 d . . . . .
H8A H 0.513760 0.184524 -0.046713 0.057 Uiso 1 1 calc R U . . .
H8B H 0.477586 0.213713 0.089965 0.057 Uiso 1 1 calc R U . . .
C9 C 0.3498(2) -0.05710(16) -0.09833(15) 0.0451(4) Uani 1 1 d . . . . .
H9A H 0.245025 -0.112772 -0.120441 0.054 Uiso 1 1 calc R U . . .
H9B H 0.366742 -0.020807 -0.179460 0.054 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C5 N1 C1 117.63(14) . .
C6 N2 C4 125.36(12) . .
C6 N2 H2 117.3 . .
C4 N2 H2 117.3 . .
N1 C1 C2 122.48(16) . .
N1 C1 H1 118.8 . .
C2 C1 H1 118.8 . .
C3 C2 C1 119.48(15) . .
C3 C2 H2A 120.3 . .
C1 C2 H2A 120.3 . .
C2 C3 C4 119.33(15) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C3 C4 C5 117.27(14) . .
C3 C4 N2 120.42(13) . .
C5 C4 N2 122.29(13) . .
N1 C5 C4 123.78(14) . .
N1 C5 H5 118.1 . .
C4 C5 H5 118.1 . .
O1 C6 N2 122.15(15) . .
O1 C6 C7 121.82(13) . .
N2 C6 C7 116.01(13) . .
C6 C7 C9 111.46(13) . .
C6 C7 C8 109.74(12) . .
C9 C7 C8 109.69(12) . .
C6 C7 H7 108.6 . .
C9 C7 H7 108.6 . .
C8 C7 H7 108.6 . .
C9 C8 C7 111.39(12) 3_655 .
C9 C8 H8A 109.3 3_655 .
C7 C8 H8A 109.3 . .
C9 C8 H8B 109.3 3_655 .
C7 C8 H8B 109.3 . .
H8A C8 H8B 108.0 . .
C8 C9 C7 110.96(13) 3_655 .
C8 C9 H9A 109.4 3_655 .
C7 C9 H9A 109.4 . .
C8 C9 H9B 109.4 3_655 .
C7 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.2255(17) .
N1 C5 1.332(2) .
N1 C1 1.336(2) .
N2 C6 1.3588(19) .
N2 C4 1.4058(19) .
N2 H2 0.8600 .
C1 C2 1.376(2) .
C1 H1 0.9300 .
C2 C3 1.372(2) .
C2 H2A 0.9300 .
C3 C4 1.382(2) .
C3 H3 0.9300 .
C4 C5 1.393(2) .
C5 H5 0.9300 .
C6 C7 1.507(2) .
C7 C9 1.525(2) .
C7 C8 1.530(2) .
C7 H7 0.9800 .
C8 C9 1.518(2) 3_655
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
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
C5 N1 C1 C2 -0.6(2) . . . .
N1 C1 C2 C3 1.0(3) . . . .
C1 C2 C3 C4 0.1(2) . . . .
C2 C3 C4 C5 -1.6(2) . . . .
C2 C3 C4 N2 179.94(14) . . . .
C6 N2 C4 C3 -145.84(16) . . . .
C6 N2 C4 C5 35.7(2) . . . .
C1 N1 C5 C4 -1.0(2) . . . .
C3 C4 C5 N1 2.1(2) . . . .
N2 C4 C5 N1 -179.46(15) . . . .
C4 N2 C6 O1 -4.3(3) . . . .
C4 N2 C6 C7 173.88(13) . . . .
O1 C6 C7 C9 -44.1(2) . . . .
N2 C6 C7 C9 137.71(15) . . . .
O1 C6 C7 C8 77.59(19) . . . .
N2 C6 C7 C8 -100.57(16) . . . .
C6 C7 C8 C9 -179.52(11) . . . 3_655
C9 C7 C8 C9 -56.75(18) . . . 3_655
C6 C7 C9 C8 178.24(12) . . . 3_655
C8 C7 C9 C8 56.50(18) . . . 3_655
