#------------------------------------------------------------------------------
#$Date: 2022-10-25 05:18:05 +0300 (Tue, 25 Oct 2022) $
#$Revision: 278766 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022687.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022687
loop_
_publ_author_name
'Gupta, Sakuntala'
'Das, Partha Pratim'
'Crispini, Alessandra'
'Scarpelli, Francesca'
'Borbone, Fabio'
'Centore, Roberto'
_publ_section_title
;
 Crystal and mesophase structure of a bicyclohexyl cyano mesogen
;
_journal_coeditor_code           YP3226
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622010105
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C22 H31 N'
_chemical_formula_moiety         'C22 H31 N'
_chemical_formula_sum            'C22 H31 N'
_chemical_formula_weight         309.48
_chemical_name_common
;
1-Cyano-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]benzene
;
_chemical_name_systematic
;
4-[trans-4-(trans-4-Propylcyclohexyl)cyclohexyl]benzonitrile
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                104.686(12)
_cell_angle_beta                 103.935(14)
_cell_angle_gamma                98.024(15)
_cell_formula_units_Z            2
_cell_length_a                   9.6230(7)
_cell_length_b                   10.1300(18)
_cell_length_c                   10.1510(18)
_cell_measurement_reflns_used    93
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.034
_cell_measurement_theta_min      3.522
_cell_volume                     907.6(3)
_computing_cell_refinement
;
DIRAX/LSQ (Duisenberg et al., 2000)
;
_computing_data_collection
;
COLLECT (Nonius, 1999)
;
_computing_data_reduction
;
EvalCCD (Duisenberg et al., 2003)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD'
_diffrn_measurement_method
;
CCD rotation images, thick slices
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12255
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.543
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker--Nonius, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.148
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0434
_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)+(0.0719P)²+0.1945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                3129
_reflns_number_total             4117
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yp3226sup1.cif
_cod_data_source_block           I
_cod_database_code               2022687
_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   0.975
_shelx_estimated_absorpt_t_max   0.981
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.84162(15) 0.01984(16) -0.39658(15) 0.0397(3) Uani d 1 . .
H H1A 0.888723 -0.025297 -0.328427 0.060 Uiso calc 1 . .
H H1B 0.916926 0.078691 -0.419040 0.060 Uiso calc 1 . .
H H1C 0.780508 -0.051747 -0.483822 0.060 Uiso calc 1 . .
C C2 0.74624(14) 0.10988(13) -0.33195(14) 0.0317(3) Uani d 1 . .
H H2A 0.808502 0.182382 -0.244214 0.038 Uiso calc 1 . .
H H2B 0.701566 0.157776 -0.399839 0.038 Uiso calc 1 . .
C C3 0.62548(13) 0.02422(12) -0.29644(13) 0.0280(3) Uani d 1 . .
H H3A 0.671443 -0.016565 -0.222359 0.034 Uiso calc 1 . .
H H3B 0.570598 -0.054134 -0.382398 0.034 Uiso calc 1 . .
C C4 0.51666(12) 0.10492(11) -0.24414(12) 0.0230(2) Uani d 1 . .
H H4 0.474927 0.150023 -0.317219 0.028 Uiso calc 1 . .
C C5 0.39027(13) 0.00589(12) -0.22930(12) 0.0259(3) Uani d 1 . .
H H5A 0.430384 -0.044702 -0.162272 0.031 Uiso calc 1 . .
H H5B 0.340118 -0.064108 -0.322877 0.031 Uiso calc 1 . .
C C6 0.27836(12) 0.08118(12) -0.17608(12) 0.0253(2) Uani d 1 . .
H H6A 0.202860 0.012472 -0.163207 0.030 Uiso calc 1 . .
H H6B 0.228968 0.121602 -0.249001 0.030 Uiso calc 1 . .
C C7 0.34774(12) 0.19771(12) -0.03552(11) 0.0226(2) Uani d 1 . .
H H7 0.389643 0.153353 0.038192 0.027 Uiso calc 1 . .
C C8 0.47497(13) 0.29588(12) -0.05101(13) 0.0283(3) Uani d 1 . .
H H8A 0.435337 0.345942 -0.118755 0.034 Uiso calc 1 . .
H H8B 0.525248 0.366384 0.042222 0.034 Uiso calc 1 . .
C C9 0.58641(13) 0.21933(13) -0.10332(13) 0.0287(3) Uani d 1 . .
H H9A 0.663549 0.287426 -0.114815 0.034 Uiso calc 1 . .
H H9B 0.633736 0.177436 -0.030810 0.034 Uiso calc 1 . .
C C10 0.23605(12) 0.27698(11) 0.01610(11) 0.0223(2) Uani d 1 . .
H H10 0.202136 0.330148 -0.051758 0.027 Uiso calc 1 . .
C C11 0.10115(13) 0.17884(13) 0.01877(13) 0.0283(3) Uani d 1 . .
H H11A 0.050446 0.117191 -0.078976 0.034 Uiso calc 1 . .
H H11B 0.133433 0.118955 0.078465 0.034 Uiso calc 1 . .
C C12 -0.00672(12) 0.25675(13) 0.07645(12) 0.0283(3) Uani d 1 . .
H H12A -0.089174 0.188293 0.079434 0.034 Uiso calc 1 . .
H H12B -0.047150 0.309011 0.011295 0.034 Uiso calc 1 . .
C C13 0.06575(12) 0.35873(12) 0.22571(11) 0.0233(2) Uani d 1 . .
H H13 0.104632 0.303059 0.289162 0.028 Uiso calc 1 . .
C C14 0.19631(13) 0.45952(12) 0.22088(13) 0.0278(3) Uani d 1 . .
H H14A 0.246601 0.523231 0.317795 0.033 Uiso calc 1 . .
H H14B 0.161054 0.516882 0.159335 0.033 Uiso calc 1 . .
C C15 0.30514(12) 0.38222(13) 0.16392(12) 0.0281(3) Uani d 1 . .
H H15A 0.347324 0.332423 0.230929 0.034 Uiso calc 1 . .
H H15B 0.386352 0.451333 0.159835 0.034 Uiso calc 1 . .
C C16 -0.04613(12) 0.42781(12) 0.28390(11) 0.0228(2) Uani d 1 . .
C C17 -0.16062(14) 0.34635(13) 0.30854(14) 0.0312(3) Uani d 1 . .
H H17 -0.165307 0.248868 0.290450 0.037 Uiso calc 1 . .
C C18 -0.26768(14) 0.40267(13) 0.35845(14) 0.0309(3) Uani d 1 . .
H H18 -0.345100 0.344560 0.373460 0.037 Uiso calc 1 . .
C C19 -0.26044(12) 0.54539(12) 0.38634(11) 0.0243(2) Uani d 1 . .
C C20 -0.14628(14) 0.62888(13) 0.36475(14) 0.0327(3) Uani d 1 . .
H H20 -0.140452 0.726670 0.384918 0.039 Uiso calc 1 . .
C C21 -0.04058(14) 0.57022(13) 0.31384(14) 0.0318(3) Uani d 1 . .
H H21 0.036973 0.628502 0.299196 0.038 Uiso calc 1 . .
C C22 -0.37016(13) 0.60842(12) 0.43798(12) 0.0265(3) Uani d 1 . .
N N1 -0.45588(12) 0.66094(11) 0.47855(12) 0.0343(3) Uani d 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C1 . . 112.11(11) ?
C3 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
C3 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C2 C3 C4 . . 115.12(10) ?
C2 C3 H3A . . 108.5 ?
C4 C3 H3A . . 108.5 ?
C2 C3 H3B . . 108.5 ?
C4 C3 H3B . . 108.5 ?
H3A C3 H3B . . 107.5 ?
C9 C4 C5 . . 109.06(9) ?
C9 C4 C3 . . 113.27(9) ?
C5 C4 C3 . . 110.65(9) ?
C9 C4 H4 . . 107.9 ?
C5 C4 H4 . . 107.9 ?
C3 C4 H4 . . 107.9 ?
C4 C5 C6 . . 112.96(9) ?
C4 C5 H5A . . 109.0 ?
C6 C5 H5A . . 109.0 ?
C4 C5 H5B . . 109.0 ?
C6 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C5 C6 C7 . . 112.75(9) ?
C5 C6 H6A . . 109.0 ?
C7 C6 H6A . . 109.0 ?
C5 C6 H6B . . 109.0 ?
C7 C6 H6B . . 109.0 ?
H6A C6 H6B . . 107.8 ?
C6 C7 C8 . . 109.04(9) ?
C6 C7 C10 . . 112.92(9) ?
C8 C7 C10 . . 111.98(9) ?
C6 C7 H7 . . 107.6 ?
C8 C7 H7 . . 107.6 ?
C10 C7 H7 . . 107.6 ?
C9 C8 C7 . . 112.88(9) ?
C9 C8 H8A . . 109.0 ?
C7 C8 H8A . . 109.0 ?
C9 C8 H8B . . 109.0 ?
C7 C8 H8B . . 109.0 ?
H8A C8 H8B . . 107.8 ?
C4 C9 C8 . . 112.38(9) ?
C4 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
C4 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.9 ?
C15 C10 C11 . . 108.96(9) ?
C15 C10 C7 . . 111.68(9) ?
C11 C10 C7 . . 112.56(9) ?
C15 C10 H10 . . 107.8 ?
C11 C10 H10 . . 107.8 ?
C7 C10 H10 . . 107.8 ?
C12 C11 C10 . . 112.91(10) ?
C12 C11 H11A . . 109.0 ?
C10 C11 H11A . . 109.0 ?
C12 C11 H11B . . 109.0 ?
C10 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C11 C12 C13 . . 111.99(9) ?
C11 C12 H12A . . 109.2 ?
C13 C12 H12A . . 109.2 ?
C11 C12 H12B . . 109.2 ?
C13 C12 H12B . . 109.2 ?
H12A C12 H12B . . 107.9 ?
C16 C13 C14 . . 114.86(9) ?
C16 C13 C12 . . 110.77(9) ?
C14 C13 C12 . . 108.66(9) ?
C16 C13 H13 . . 107.4 ?
C14 C13 H13 . . 107.4 ?
C12 C13 H13 . . 107.4 ?
C13 C14 C15 . . 111.68(9) ?
C13 C14 H14A . . 109.3 ?
C15 C14 H14A . . 109.3 ?
C13 C14 H14B . . 109.3 ?
C15 C14 H14B . . 109.3 ?
H14A C14 H14B . . 107.9 ?
C14 C15 C10 . . 113.20(9) ?
C14 C15 H15A . . 108.9 ?
C10 C15 H15A . . 108.9 ?
C14 C15 H15B . . 108.9 ?
C10 C15 H15B . . 108.9 ?
H15A C15 H15B . . 107.8 ?
C21 C16 C17 . . 117.61(10) ?
C21 C16 C13 . . 122.91(10) ?
C17 C16 C13 . . 119.48(10) ?
C18 C17 C16 . . 122.19(11) ?
C18 C17 H17 . . 118.9 ?
C16 C17 H17 . . 118.9 ?
C17 C18 C19 . . 119.09(11) ?
C17 C18 H18 . . 120.5 ?
C19 C18 H18 . . 120.5 ?
C20 C19 C18 . . 119.76(10) ?
C20 C19 C22 . . 119.32(10) ?
C18 C19 C22 . . 120.92(10) ?
C19 C20 C21 . . 120.24(11) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C20 C21 C16 . . 121.10(11) ?
C20 C21 H21 . . 119.4 ?
C16 C21 H21 . . 119.4 ?
N1 C22 C19 . . 178.58(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.5249(16) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 C3 . 1.5206(16) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.5276(14) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C9 . 1.5224(16) ?
C4 C5 . 1.5272(15) ?
C4 H4 . 1.0000 ?
C5 C6 . 1.5277(14) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 C7 . 1.5304(16) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.5313(15) ?
C7 C10 . 1.5405(14) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.5268(15) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C15 . 1.5300(15) ?
C10 C11 . 1.5312(16) ?
C10 H10 . 1.0000 ?
C11 C12 . 1.5265(15) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C12 C13 . 1.5315(16) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C13 C16 . 1.5182(14) ?
C13 C14 . 1.5232(16) ?
C13 H13 . 1.0000 ?
C14 C15 . 1.5282(14) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C21 . 1.3873(16) ?
C16 C17 . 1.3932(16) ?
C17 C18 . 1.3829(15) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.3893(16) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.3860(17) ?
C19 C22 . 1.4430(15) ?
C20 C21 . 1.3860(16) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
C22 N1 . 1.1438(15) ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . -174.55(10) ?
C2 C3 C4 C9 . . . . -64.17(13) ?
C2 C3 C4 C5 . . . . 173.01(10) ?
C9 C4 C5 C6 . . . . 54.31(12) ?
C3 C4 C5 C6 . . . . 179.55(9) ?
C4 C5 C6 C7 . . . . -55.35(13) ?
C5 C6 C7 C8 . . . . 53.02(12) ?
C5 C6 C7 C10 . . . . 178.17(9) ?
C6 C7 C8 C9 . . . . -53.81(13) ?
C10 C7 C8 C9 . . . . -179.50(9) ?
C5 C4 C9 C8 . . . . -54.70(12) ?
C3 C4 C9 C8 . . . . -178.40(9) ?
C7 C8 C9 C4 . . . . 56.60(13) ?
C6 C7 C10 C15 . . . . 174.04(9) ?
C8 C7 C10 C15 . . . . -62.42(12) ?
C6 C7 C10 C11 . . . . 51.10(12) ?
C8 C7 C10 C11 . . . . 174.64(9) ?
C15 C10 C11 C12 . . . . 52.83(12) ?
C7 C10 C11 C12 . . . . 177.27(9) ?
C10 C11 C12 C13 . . . . -56.52(13) ?
C11 C12 C13 C16 . . . . -176.44(9) ?
C11 C12 C13 C14 . . . . 56.51(12) ?
C16 C13 C14 C15 . . . . 178.88(9) ?
C12 C13 C14 C15 . . . . -56.44(12) ?
C13 C14 C15 C10 . . . . 56.92(13) ?
C11 C10 C15 C14 . . . . -53.11(13) ?
C7 C10 C15 C14 . . . . -178.08(9) ?
C14 C13 C16 C21 . . . . 7.75(16) ?
C12 C13 C16 C21 . . . . -115.82(13) ?
C14 C13 C16 C17 . . . . -172.51(10) ?
C12 C13 C16 C17 . . . . 63.92(14) ?
C21 C16 C17 C18 . . . . 1.20(18) ?
C13 C16 C17 C18 . . . . -178.55(11) ?
C16 C17 C18 C19 . . . . -0.62(19) ?
C17 C18 C19 C20 . . . . -0.41(18) ?
C17 C18 C19 C22 . . . . 179.75(11) ?
C18 C19 C20 C21 . . . . 0.80(19) ?
C22 C19 C20 C21 . . . . -179.35(11) ?
C19 C20 C21 C16 . . . . -0.2(2) ?
C17 C16 C21 C20 . . . . -0.79(18) ?
C13 C16 C21 C20 . . . . 178.96(11) ?

_cod_database_fobs_code 2022687
