#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/99/2209981.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_2209981
loop_
_publ_author_name
'Wu Li'
'Tao Zeng'
'Yang Li'
_publ_section_title
;
 4-(Cyclohexyliminomethyl)phenol
;
_journal_coeditor_code           RZ2054
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3432
_journal_page_last               o3433
_journal_paper_doi               10.1107/S1600536806027279
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H17 N O'
_chemical_formula_moiety         'C13 H17 N O'
_chemical_formula_sum            'C13 H17 N O'
_chemical_formula_weight         203.28
_chemical_name_systematic
;
4-(cyclohexyliminomethyl)cyclohexanol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 97.102(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.6582(16)
_cell_length_b                   17.453(5)
_cell_length_c                   11.833(3)
_cell_measurement_reflns_used    1679
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.33
_cell_volume                     1159.6(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and w\'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5807
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2043
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.1411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1158
_reflns_number_gt                1346
_reflns_number_total             2043
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2054.cif
_cod_data_source_block           I
_cod_original_cell_volume        1159.5(6)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2209981
_cod_database_fobs_code          2209981
loop_
_symmetry_equiv_pos_as_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_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_refinement_flags
_atom_site_occupancy
O O1 0.2283(2) 0.14217(7) 0.71469(12) 0.0557(4) Uani d . 1
H H1 0.367(4) 0.1299(13) 0.7626(19) 0.084 Uiso d . 1
N N1 0.1309(3) 0.41445(8) 0.34210(12) 0.0448(4) Uani d . 1
C C1 0.2754(3) 0.32175(9) 0.48816(14) 0.0392(4) Uani d . 1
C C2 0.0730(3) 0.27582(10) 0.48351(15) 0.0441(5) Uani d . 1
H H2 -0.0565 0.2859 0.4291 0.053 Uiso calc R 1
C C3 0.0618(3) 0.21588(10) 0.55805(16) 0.0448(5) Uani d . 1
H H3 -0.0748 0.1858 0.5536 0.054 Uiso calc R 1
C C4 0.2543(3) 0.19975(9) 0.64051(15) 0.0393(4) Uani d . 1
C C5 0.4583(3) 0.24327(10) 0.64434(15) 0.0432(5) Uani d . 1
H H5 0.5894 0.2322 0.6973 0.052 Uiso calc R 1
C C6 0.4670(3) 0.30366(10) 0.56886(15) 0.0440(5) Uani d . 1
H H6 0.6051 0.3329 0.5723 0.053 Uiso calc R 1
C C7 0.2899(3) 0.39083(10) 0.41958(15) 0.0442(5) Uani d . 1
H H7 0.4277 0.4201 0.4339 0.053 Uiso calc R 1
C C8 0.1686(3) 0.48971(10) 0.29011(15) 0.0472(5) Uani d . 1
H H8 0.3059 0.5147 0.3338 0.057 Uiso calc R 1
C C9 0.2186(4) 0.48027(10) 0.16845(16) 0.0530(5) Uani d . 1
H H9A 0.0910 0.4510 0.1264 0.064 Uiso calc R 1
H H9B 0.3656 0.4518 0.1673 0.064 Uiso calc R 1
C C10 0.2398(4) 0.55760(11) 0.11075(18) 0.0613(6) Uani d . 1
H H10A 0.3780 0.5846 0.1478 0.074 Uiso calc R 1
H H10B 0.2628 0.5496 0.0317 0.074 Uiso calc R 1
C C11 0.0193(4) 0.60601(11) 0.11637(17) 0.0570(6) Uani d . 1
H H11A 0.0422 0.6559 0.0833 0.068 Uiso calc R 1
H H11B -0.1158 0.5818 0.0719 0.068 Uiso calc R 1
C C12 -0.0333(4) 0.61605(11) 0.23675(18) 0.0605(6) Uani d . 1
H H12A -0.1822 0.6436 0.2366 0.073 Uiso calc R 1
H H12B 0.0918 0.6464 0.2786 0.073 Uiso calc R 1
C C13 -0.0511(4) 0.53907(10) 0.29657(16) 0.0577(6) Uani d . 1
H H13A -0.0705 0.5479 0.3758 0.069 Uiso calc R 1
H H13B -0.1909 0.5119 0.2616 0.069 Uiso calc R 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'
O O 0.0106 0.0060 '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_publ_flag
C4 O1 H1 114.3(14) ?
C7 N1 C8 117.58(15) yes
C6 C1 C2 117.65(16) ?
C6 C1 C7 118.44(16) yes
C2 C1 C7 123.72(16) ?
C3 C2 C1 121.00(16) ?
C3 C2 H2 119.5 ?
C1 C2 H2 119.5 ?
C2 C3 C4 120.49(16) ?
C2 C3 H3 119.8 ?
C4 C3 H3 119.8 ?
O1 C4 C5 123.05(15) yes
O1 C4 C3 117.66(15) ?
C5 C4 C3 119.28(15) ?
C4 C5 C6 119.62(16) ?
C4 C5 H5 120.2 ?
C6 C5 H5 120.2 ?
C5 C6 C1 121.91(16) ?
C5 C6 H6 119.0 ?
C1 C6 H6 119.0 ?
N1 C7 C1 125.77(17) ?
N1 C7 H7 117.1 ?
C1 C7 H7 117.1 ?
N1 C8 C9 110.71(14) ?
N1 C8 C13 108.76(16) ?
C9 C8 C13 111.11(15) ?
N1 C8 H8 108.7 ?
C9 C8 H8 108.7 ?
C13 C8 H8 108.7 ?
C8 C9 C10 111.39(16) ?
C8 C9 H9A 109.3 ?
C10 C9 H9A 109.3 ?
C8 C9 H9B 109.3 ?
C10 C9 H9B 109.3 ?
H9A C9 H9B 108.0 ?
C11 C10 C9 111.30(17) ?
C11 C10 H10A 109.4 ?
C9 C10 H10A 109.4 ?
C11 C10 H10B 109.4 ?
C9 C10 H10B 109.4 ?
H10A C10 H10B 108.0 ?
C12 C11 C10 111.57(16) ?
C12 C11 H11A 109.3 ?
C10 C11 H11A 109.3 ?
C12 C11 H11B 109.3 ?
C10 C11 H11B 109.3 ?
H11A C11 H11B 108.0 ?
C11 C12 C13 111.66(16) ?
C11 C12 H12A 109.3 ?
C13 C12 H12A 109.3 ?
C11 C12 H12B 109.3 ?
C13 C12 H12B 109.3 ?
H12A C12 H12B 107.9 ?
C8 C13 C12 111.92(18) ?
C8 C13 H13A 109.2 ?
C12 C13 H13A 109.2 ?
C8 C13 H13B 109.2 ?
C12 C13 H13B 109.2 ?
H13A C13 H13B 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.354(2) yes
O1 H1 0.94(2) ?
N1 C7 1.271(2) yes
N1 C8 1.477(2) yes
C1 C6 1.390(2) ?
C1 C2 1.393(2) ?
C1 C7 1.461(2) ?
C2 C3 1.375(2) ?
C2 H2 0.9300 ?
C3 C4 1.398(2) ?
C3 H3 0.9300 ?
C4 C5 1.378(2) ?
C5 C6 1.386(2) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.510(3) ?
C8 C13 1.522(3) ?
C8 H8 0.9800 ?
C9 C10 1.524(3) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.515(3) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C12 1.501(3) ?
C11 H11A 0.9700 ?
C11 H11B 0.9700 ?
C12 C13 1.528(3) ?
C12 H12A 0.9700 ?
C12 H12B 0.9700 ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 4_666 0.94(2) 1.83(2) 2.755(2) 168(2) yes
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_publ_flag
C6 C1 C2 C3 1.5(3) ?
C7 C1 C2 C3 -173.49(17) ?
C1 C2 C3 C4 0.0(3) ?
C2 C3 C4 O1 177.08(16) ?
C2 C3 C4 C5 -1.8(3) ?
O1 C4 C5 C6 -176.88(16) yes
C3 C4 C5 C6 1.9(3) ?
C4 C5 C6 C1 -0.4(3) ?
C2 C1 C6 C5 -1.4(3) ?
C7 C1 C6 C5 173.91(17) ?
C8 N1 C7 C1 174.06(16) ?
C6 C1 C7 N1 179.32(17) ?
C2 C1 C7 N1 -5.7(3) yes
C7 N1 C8 C9 110.41(18) ?
C7 N1 C8 C13 -127.25(17) yes
N1 C8 C9 C10 175.82(16) ?
C13 C8 C9 C10 54.9(2) ?
C8 C9 C10 C11 -55.8(2) ?
C9 C10 C11 C12 55.5(2) ?
C10 C11 C12 C13 -54.3(2) ?
N1 C8 C13 C12 -175.92(15) yes
C9 C8 C13 C12 -53.8(2) ?
C11 C12 C13 C8 53.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655021
2 PubChem 241238
