#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/26/2202626.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_2202626
loop_
_publ_author_name
'de Sousa, Alvaro S.'
'Fernandes, Manuel A.'
_publ_section_title
;
 N,N'-Bis(2-hydroxycyclohexyl)-trans-cyclohexane-1,2-diamine:
 a structure reanalysed at low temperature
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1872
_journal_page_last               o1874
_journal_paper_doi               10.1107/S1600536803024826
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C18 H34 N2 O2'
_chemical_formula_moiety         'C18 H34 N2 O2'
_chemical_formula_sum            'C18 H34 N2 O2'
_chemical_formula_weight         310.47
_chemical_name_systematic
;
N,N'-bis(2-hydroxycyclohexyl)-trans-cyclohexane-1,2-diamine
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 123.074(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8682(17)
_cell_length_b                   17.512(3)
_cell_length_c                   10.2790(15)
_cell_measurement_reflns_used    975
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.29
_cell_measurement_theta_min      2.36
_cell_volume                     1790.2(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART-NT (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'SHELXTL (Bruker, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART 1K CCD'
_diffrn_measurement_method       ω
_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  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5446
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     108
_refine_ls_number_reflns         1852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0842P)²+0.6514P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                1514
_reflns_number_total             1852
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6105.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2202626
_cod_database_fobs_code          2202626
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N1 0.87482(11) 0.26213(6) 0.24675(12) 0.0180(3) Uani d . 1 . . N
H111 0.7916(17) 0.2784(9) 0.1813(18) 0.028(4) Uiso d . 1 . . H
O1 1.11126(8) 0.17741(5) 0.47534(10) 0.0233(3) Uani d . 1 . . O
H112 1.109(2) 0.2033(11) 0.389(2) 0.059(6) Uiso d . 1 . . H
C1 0.97922(12) 0.15161(7) 0.42255(14) 0.0190(3) Uani d . 1 . . C
H1 0.9483 0.1167 0.3321 0.023 Uiso calc R 1 . . H
C2 0.87922(12) 0.21767(7) 0.37096(13) 0.0181(3) Uani d . 1 . . C
H2 0.9082 0.2519 0.4618 0.022 Uiso calc R 1 . . H
C3 0.74017(13) 0.18527(7) 0.31501(15) 0.0213(3) Uani d . 1 . . C
H3A 0.6749 0.2277 0.2821 0.026 Uiso calc R 1 . . H
H3B 0.7102 0.1519 0.2240 0.026 Uiso calc R 1 . . H
C4 0.74285(13) 0.13952(7) 0.44323(15) 0.0236(3) Uani d . 1 . . C
H4A 0.7644 0.1740 0.5302 0.028 Uiso calc R 1 . . H
H4B 0.6528 0.1173 0.4025 0.028 Uiso calc R 1 . . H
C5 0.84701(14) 0.07554(8) 0.50288(16) 0.0255(3) Uani d . 1 . . C
H5A 0.8185 0.0370 0.4200 0.031 Uiso calc R 1 . . H
H5B 0.8526 0.0501 0.5922 0.031 Uiso calc R 1 . . H
C6 0.98533(13) 0.10659(7) 0.55290(15) 0.0232(3) Uani d . 1 . . C
H6A 1.0189 0.1401 0.6446 0.028 Uiso calc R 1 . . H
H6B 1.0491 0.0636 0.5832 0.028 Uiso calc R 1 . . H
C7 0.96625(12) 0.32917(7) 0.29608(14) 0.0181(3) Uani d . 1 . . C
H7 1.0381 0.3229 0.4086 0.022 Uiso calc R 1 . . H
C8 0.89101(13) 0.40360(7) 0.27741(15) 0.0216(3) Uani d . 1 . . C
H8A 0.8094 0.4060 0.1710 0.026 Uiso calc R 1 . . H
H8B 0.8618 0.4035 0.3511 0.026 Uiso calc R 1 . . H
C9 0.97674(13) 0.47427(7) 0.30632(14) 0.0217(3) Uani d . 1 . . C
H9A 1.0558 0.4741 0.4147 0.026 Uiso calc R 1 . . H
H9B 0.9236 0.5209 0.2908 0.026 Uiso calc R 1 . . H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C7 . . 116.61(9) yes
C2 N1 H111 . . 109.0(10) yes
C7 N1 H111 . . 108.0(10) yes
C1 O1 H112 . . 108.5(12) ?
O1 C1 C6 . . 108.37(10) ?
O1 C1 C2 . . 112.12(10) ?
C6 C1 C2 . . 110.61(10) ?
O1 C1 H1 . . 108.6 ?
C6 C1 H1 . . 108.6 ?
C2 C1 H1 . . 108.6 ?
N1 C2 C3 . . 110.47(10) ?
N1 C2 C1 . . 110.74(9) ?
C3 C2 C1 . . 108.87(10) ?
N1 C2 H2 . . 108.9 ?
C3 C2 H2 . . 108.9 ?
C1 C2 H2 . . 108.9 ?
C4 C3 C2 . . 111.09(10) ?
C4 C3 H3A . . 109.4 ?
C2 C3 H3A . . 109.4 ?
C4 C3 H3B . . 109.4 ?
C2 C3 H3B . . 109.4 ?
H3A C3 H3B . . 108.0 ?
C5 C4 C3 . . 111.25(10) ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C4 C5 C6 . . 111.08(11) ?
C4 C5 H5A . . 109.4 ?
C6 C5 H5A . . 109.4 ?
C4 C5 H5B . . 109.4 ?
C6 C5 H5B . . 109.4 ?
H5A C5 H5B . . 108.0 ?
C1 C6 C5 . . 111.22(10) ?
C1 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
C1 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
N1 C7 C8 . . 111.22(10) ?
N1 C7 C7 . 2_755 108.55(8) ?
C8 C7 C7 . 2_755 112.75(8) ?
N1 C7 H7 . . 108.1 ?
C8 C7 H7 . . 108.1 ?
C7 C7 H7 2_755 . 108.1 ?
C9 C8 C7 . . 112.64(10) ?
C9 C8 H8A . . 109.1 ?
C7 C8 H8A . . 109.1 ?
C9 C8 H8B . . 109.1 ?
C7 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
C8 C9 C9 . 2_755 109.29(9) ?
C8 C9 H9A . . 109.8 ?
C9 C9 H9A 2_755 . 109.8 ?
C8 C9 H9B . . 109.8 ?
C9 C9 H9B 2_755 . 109.8 ?
H9A C9 H9B . . 108.3 ?
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
N1 C2 . 1.4718(15) ?
N1 C7 . 1.4874(15) ?
N1 H111 . 0.885(17) ?
O1 C1 . 1.4234(15) ?
O1 H112 . 0.99(2) ?
C1 C6 . 1.5218(17) ?
C1 C2 . 1.5301(17) ?
C1 H1 . 1.0000 ?
C2 C3 . 1.5298(17) ?
C2 H2 . 1.0000 ?
C3 C4 . 1.5278(18) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 C5 . 1.5271(19) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.5276(18) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.5317(17) ?
C7 C7 2_755 1.539(2) ?
C7 H7 . 1.0000 ?
C8 C9 . 1.5250(17) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C9 2_755 1.531(2) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
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
N1 H111 O1 8_455 0.885(17) 2.172(17) 3.0273(14) 162.2(14) yes
O1 H112 N1 2_755 0.99(2) 1.82(2) 2.8021(14) 170.3(17) yes
C8 H8A O1 8_455 0.99 2.56 3.3800(16) 140 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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C2 C3 . . . 146.80(10) ?
C7 N1 C2 C1 . . . -92.50(12) ?
O1 C1 C2 N1 . . . 57.93(12) ?
C6 C1 C2 N1 . . . 179.02(9) ?
O1 C1 C2 C3 . . . 179.58(9) ?
C6 C1 C2 C3 . . . -59.33(12) ?
N1 C2 C3 C4 . . . -179.51(9) ?
C1 C2 C3 C4 . . . 58.67(13) ?
C2 C3 C4 C5 . . . -56.49(14) ?
C3 C4 C5 C6 . . . 53.77(14) ?
O1 C1 C6 C5 . . . -178.75(10) ?
C2 C1 C6 C5 . . . 57.97(13) ?
C4 C5 C6 C1 . . . -54.68(14) ?
C2 N1 C7 C8 . . . -99.60(12) ?
C2 N1 C7 C7 . . 2_755 135.80(11) ?
N1 C7 C8 C9 . . . -172.39(9) ?
C7 C7 C8 C9 2_755 . . -50.19(16) yes
C7 C8 C9 C9 . . 2_755 58.23(15) ?
C8 C7 C7 C8 . 2_755 2_755 45.3(2) yes
N1 C7 C7 N1 . 2_755 2_755 -67.27(17) yes
