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#$Date: 2022-03-15 11:32:52 +0200 (Tue, 15 Mar 2022) $
#$Revision: 273690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/47/8104753.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_8104753
loop_
_publ_author_name
'Hosten, Eric C.'
'Betz, Richard'
_publ_section_title
;
 The crystal structure of
 N-(4-(cyclohexylimino)pent-2-en-2-yl)cyclohexanamine, C17H30N2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              515
_journal_page_last               517
_journal_paper_doi               10.1515/ncrs-2020-0579
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C17 H30 N2'
_chemical_formula_sum            'C17 H30 N2'
_chemical_formula_weight         262.43
_chemical_name_common            2,4-dicyclohexyliminepentane
_chemical_name_systematic        2,4-dicyclohexyliminepentane
_space_group_crystal_system      tetragonal
_space_group_IT_number           113
_space_group_name_Hall           'P -4 2ab'
_space_group_name_H-M_alt        'P -4 21 m'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXS
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6755(3)
_cell_length_b                   8.6755(3)
_cell_length_c                   11.1611(4)
_cell_measurement_reflns_used    7237
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.89
_cell_measurement_theta_min      2.97
_cell_volume                     840.03(5)
_computing_cell_refinement       'SAINT [1]'
_computing_data_collection       'APEX2 [1]'
_computing_data_reduction        'SAINT [1]'
_computing_molecular_graphics    'ORTEP3 [3], Mercury [4]'
_computing_publication_material  'SHELXL-97 [2], PLATON [5]'
_computing_structure_refinement  'SHELXL-97 [2]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0094
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15310
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_min         2.974
_exptl_absorpt_coefficient_mu    0.060
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9611
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;                                                              
SADABS[6]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.038
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
Due to the absence of a strong anomalous scatterer, the Flack parameter is 
meaningless. Thus, the item was removed from the CIF.  
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     54
_refine_ls_number_reflns         1137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0488
_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)+(0.0796P)²+0.1267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1417
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                1039
_reflns_number_total             1137
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0579_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        840.03(7)
_cod_database_code               8104753
_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   0.972
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, 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
N1 N 0.39158(18) 0.89158(18) 0.36448(19) 0.0420(6) Uani 1 2 d S T P . .
H1 H 0.451763 0.951763 0.324968 0.063 Uiso 0.5 2 calc R U P . .
C1 C 0.39792(19) 0.89792(19) 0.4820(2) 0.0355(5) Uani 1 2 d S T P . .
C2 C 0.500000 1.000000 0.5396(3) 0.0371(7) Uani 1 4 d S T P . .
H2 H 0.500000 1.000000 0.622890 0.045 Uiso 1 4 calc R U P . .
C3 C 0.2970(3) 0.7970(3) 0.5587(3) 0.0655(10) Uani 1 2 d S T P . .
H3A H 0.192131 0.831667 0.553316 0.098 Uiso 0.5 1 calc R U P . .
H3B H 0.330805 0.802556 0.640481 0.098 Uiso 0.5 1 calc R U P . .
H3C H 0.303637 0.692350 0.531190 0.098 Uiso 0.5 1 calc R U P . .
C11 C 0.2909(2) 0.7909(2) 0.2961(2) 0.0416(6) Uani 1 2 d S T P . .
H11 H 0.228668 0.728667 0.351165 0.050 Uiso 1 2 calc R U P . .
C12 C 0.3870(3) 0.6856(3) 0.2174(2) 0.0640(7) Uani 1 1 d . . . . .
H12A H 0.451076 0.620586 0.267528 0.077 Uiso 1 1 calc R U . . .
H12B H 0.454316 0.747489 0.167399 0.077 Uiso 1 1 calc R U . . .
C13 C 0.2859(4) 0.5841(3) 0.1377(2) 0.0705(8) Uani 1 1 d . . . . .
H13A H 0.351072 0.522472 0.085862 0.085 Uiso 1 1 calc R U . . .
H13B H 0.226526 0.514397 0.187580 0.085 Uiso 1 1 calc R U . . .
C14 C 0.1781(3) 0.6781(3) 0.0625(3) 0.0556(7) Uani 1 2 d S T P . .
H14A H 0.237044 0.737043 0.004572 0.067 Uiso 1 2 calc R U P . .
H14B H 0.109783 0.609783 0.018698 0.067 Uiso 1 2 calc R U P . .
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
C1 N1 C11 125.1(2) . .
C1 N1 H1 117.5 . .
C11 N1 H1 117.5 . .
N1 C1 C2 120.5(2) . .
N1 C1 C3 121.2(2) . .
C2 C1 C3 118.2(2) . .
C1 C2 C1 125.7(3) . 2_675
C1 C2 H2 117.1 . .
C1 C2 H2 117.1 2_675 .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C1 C3 H3A 109.5(5) . 8_455
H3A C3 H3A 126.2 . 8_455
H3B C3 H3A 90.7 . 8_455
C1 C3 H3B 109(4) . 8_455
H3A C3 H3B 90.7 . 8_455
H3C C3 H3B 126.2 . 8_455
H3A C3 H3B 109.5 8_455 8_455
C1 C3 H3C 109(2) . 8_455
H3B C3 H3C 126.2 . 8_455
H3C C3 H3C 90.7 . 8_455
H3A C3 H3C 109.5 8_455 8_455
H3B C3 H3C 109.5 8_455 8_455
N1 C11 C12 109.66(15) . .
N1 C11 C12 109.66(15) . 8_455
C12 C11 C12 109.0(2) . 8_455
N1 C11 H11 109.5 . .
C12 C11 H11 109.5 . .
C12 C11 H11 109.5 8_455 .
C11 C12 C13 111.6(2) . .
C11 C12 H12A 109.3 . .
C13 C12 H12A 109.3 . .
C11 C12 H12B 109.3 . .
C13 C12 H12B 109.3 . .
H12A C12 H12B 108.0 . .
C14 C13 C12 111.8(2) . .
C14 C13 H13A 109.3 . .
C12 C13 H13A 109.3 . .
C14 C13 H13B 109.3 . .
C12 C13 H13B 109.3 . .
H13A C13 H13B 107.9 . .
C13 C14 C13 111.4(3) 8_455 .
C13 C14 H14A 109.3 8_455 .
C13 C14 H14A 109.3 . .
C13 C14 H14B 109.3 8_455 .
C13 C14 H14B 109.3 . .
H14A C14 H14B 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.314(3) .
N1 C11 1.452(3) .
N1 H1 0.8600 .
C1 C2 1.407(3) .
C1 C3 1.505(4) .
C2 H2 0.9300 .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
C3 H3A 0.96(3) 8_455
C3 H3B 0.96(3) 8_455
C3 H3C 0.960(4) 8_455
C11 C12 1.517(2) .
C11 C12 1.517(2) 8_455
C11 H11 0.9800 .
C12 C13 1.528(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.498(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N1 0.86 1.97 2.660(4) 136.2 2_675
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
C11 N1 C1 C2 180.000(0) . . . .
C11 N1 C1 C3 0.000(1) . . . .
N1 C1 C2 C1 0.000(1) . . . 2_675
C3 C1 C2 C1 180.000(0) . . . 2_675
C1 N1 C11 C12 -120.17(15) . . . .
C1 N1 C11 C12 120.17(15) . . . 8_455
N1 C11 C12 C13 -176.4(2) . . . .
C12 C11 C12 C13 -56.4(3) 8_455 . . .
C11 C12 C13 C14 56.0(3) . . . .
C12 C13 C14 C13 -53.9(4) . . . 8_455
