#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/14/2231468.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_2231468
loop_
_publ_author_name
'Qian, Hui-Fen'
'Huang, Wei'
_publ_section_title
;
 4,4'-(Cyclohexane-1,1-diyl)dianilinium dichloride monohydrate
;
_journal_coeditor_code           FF2022
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2420
_journal_paper_doi               10.1107/S1600536811032995
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C18 H24 N2 2+, 2Cl -, H2 O'
_chemical_formula_moiety         'C18 H24 N2 2+, 2(Cl -), H2 O'
_chemical_formula_sum            'C18 H26 Cl2 N2 O'
_chemical_formula_weight         357.31
_chemical_name_systematic
;
4,4'-(Cyclohexane-1,1-diyl)dianilinium dichloride monohydrate
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 107.085(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.442(3)
_cell_length_b                   9.548(4)
_cell_length_c                   12.098(5)
_cell_measurement_reflns_used    1254
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.494
_cell_measurement_theta_min      2.524
_cell_volume                     932.1(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker 1K CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.1024
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4705
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.9654
_exptl_absorpt_correction_T_min  0.9587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.505
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0653
_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)+(0.1167P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1892
_refine_ls_wR_factor_ref         0.2124
_reflns_number_gt                1158
_reflns_number_total             1735
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ff2022.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2231468
_cod_database_fobs_code          2231468
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.9232(4) 0.2500 -0.0868(3) 0.0294(9) Uani d S 1 2
C C2 1.0908(5) 0.2500 -0.0779(3) 0.0359(9) Uani d S 1 2
H H2 1.1675 0.2500 -0.0048 0.043 Uiso calc SR 1 2
C C3 1.1484(5) 0.2500 -0.1747(4) 0.0417(10) Uani d S 1 2
H H3 1.2616 0.2500 -0.1659 0.050 Uiso calc SR 1 2
C C4 1.0383(5) 0.2500 -0.2816(3) 0.0386(10) Uani d S 1 2
C C5 0.8702(5) 0.2500 -0.2956(3) 0.0425(10) Uani d S 1 2
H H5 0.7954 0.2500 -0.3694 0.051 Uiso calc SR 1 2
C C6 0.8136(5) 0.2500 -0.1994(3) 0.0372(10) Uani d S 1 2
H H6 0.7000 0.2500 -0.2095 0.045 Uiso calc SR 1 2
C C7 0.8564(4) 0.2500 0.0183(3) 0.0319(9) Uani d S 1 2
C C8 0.7457(3) 0.1189(3) 0.0130(2) 0.0424(8) Uani d . 1 1
H H8A 0.6611 0.1165 -0.0613 0.051 Uiso calc R 1 1
H H8B 0.8131 0.0354 0.0190 0.051 Uiso calc R 1 1
C C9 0.6634(4) 0.1176(4) 0.1081(3) 0.0613(11) Uani d . 1 1
H H9A 0.7474 0.1105 0.1824 0.074 Uiso calc R 1 1
H H9B 0.5920 0.0362 0.0991 0.074 Uiso calc R 1 1
C C10 0.5613(6) 0.2500 0.1054(4) 0.077(2) Uani d S 1 2
H H10A 0.4679 0.2500 0.0358 0.092 Uiso calc SR 1 2
H H10B 0.5181 0.2500 0.1713 0.092 Uiso calc SR 1 2
C C11 1.0029(4) 0.2500 0.1307(3) 0.0305(9) Uani d S 1 2
C C12 1.0744(3) 0.1265(3) 0.1817(2) 0.0403(8) Uani d . 1 1
H H12 1.0283 0.0417 0.1503 0.048 Uiso calc R 1 1
C C13 1.2123(4) 0.1256(3) 0.2777(2) 0.0436(8) Uani d . 1 1
H H13 1.2590 0.0414 0.3101 0.052 Uiso calc R 1 1
C C14 1.2789(5) 0.2500 0.3243(3) 0.0362(10) Uani d S 1 2
Cl Cl1 0.35794(16) 1.02159(14) 0.60558(11) 0.1036(6) Uani d . 1 1
N N1 1.1019(5) 0.2500 -0.3833(3) 0.0507(10) Uani d S 1 2
H H1A 1.1617 0.3283 -0.3818 0.061 Uiso d PR 0.50 1
H H1B 1.0163 0.2500 -0.4484 0.061 Uiso d SR 1 2
H H1C 1.1641 0.1729 -0.3814 0.061 Uiso d PR 0.50 1
N N2 1.4267(4) 0.2500 0.4255(3) 0.0493(10) Uani d S 1 2
H H2A 1.5082 0.2037 0.4086 0.059 Uiso d PR 0.50 1
H H2B 1.4031 0.2084 0.4846 0.059 Uiso d PR 0.50 1
H H2C 1.4584 0.3378 0.4446 0.059 Uiso d PR 0.50 1
O O1 0.8669(6) 0.2500 0.4122(4) 0.128(2) Uani d S 1 2
H H1D 0.8043 0.3178 0.3960 0.192 Uiso d PR 0.50 1
H H1E 0.7860 0.1950 0.3841 0.192 Uiso d PR 0.50 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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 . . 116.2(3)
C2 C1 C7 . . 123.4(3)
C6 C1 C7 . . 120.4(3)
C1 C2 C3 . . 122.3(4)
C1 C2 H2 . . 118.9
C3 C2 H2 . . 118.9
C4 C3 C2 . . 119.5(4)
C4 C3 H3 . . 120.3
C2 C3 H3 . . 120.3
C3 C4 C5 . . 120.7(4)
C3 C4 N1 . . 118.7(3)
C5 C4 N1 . . 120.6(4)
C4 C5 C6 . . 119.7(4)
C4 C5 H5 . . 120.2
C6 C5 H5 . . 120.2
C5 C6 C1 . . 121.6(4)
C5 C6 H6 . . 119.2
C1 C6 H6 . . 119.2
C1 C7 C11 . . 109.6(3)
C1 C7 C8 . . 109.2(2)
C11 C7 C8 . . 110.63(19)
C1 C7 C8 . 4_565 109.2(2)
C11 C7 C8 . 4_565 110.63(19)
C8 C7 C8 . 4_565 107.5(3)
C9 C8 C7 . . 112.4(3)
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 C10 . . 111.2(3)
C8 C9 H9A . . 109.4
C10 C9 H9A . . 109.4
C8 C9 H9B . . 109.4
C10 C9 H9B . . 109.4
H9A C9 H9B . . 108.0
C9 C10 C9 4_565 . 112.0(4)
C9 C10 H10A 4_565 . 109.2
C9 C10 H10A . . 109.2
C9 C10 H10B 4_565 . 109.2
C9 C10 H10B . . 109.2
H10A C10 H10B . . 107.9
C12 C11 C12 4_565 . 116.8(3)
C12 C11 C7 4_565 . 121.54(17)
C12 C11 C7 . . 121.54(17)
C13 C12 C11 . . 121.9(3)
C13 C12 H12 . . 119.0
C11 C12 H12 . . 119.0
C14 C13 C12 . . 119.0(3)
C14 C13 H13 . . 120.5
C12 C13 H13 . . 120.5
C13 C14 C13 . 4_565 121.2(3)
C13 C14 N2 . . 119.38(18)
C13 C14 N2 4_565 . 119.38(18)
C4 N1 H1A . . 108.8
C4 N1 H1B . . 109.5
H1A N1 H1B . . 108.6
C4 N1 H1C . . 109.3
H1A N1 H1C . . 111.0
H1B N1 H1C . . 109.6
C14 N2 H2A . . 109.5
C14 N2 H2B . . 109.5
H2A N2 H2B . . 109.5
C14 N2 H2C . . 109.5
H2A N2 H2C . . 109.5
H2B N2 H2C . . 109.5
H1D O1 H1E . . 90.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.388(5)
C1 C6 . 1.404(5)
C1 C7 . 1.535(5)
C2 C3 . 1.393(5)
C2 H2 . 0.9300
C3 C4 . 1.352(6)
C3 H3 . 0.9300
C4 C5 . 1.379(6)
C4 N1 . 1.480(5)
C5 C6 . 1.382(5)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 C11 . 1.546(5)
C7 C8 . 1.552(4)
C7 C8 4_565 1.552(4)
C8 C9 . 1.508(4)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 C10 . 1.525(5)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 C9 4_565 1.525(5)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 C12 4_565 1.384(3)
C11 C12 . 1.384(3)
C12 C13 . 1.383(4)
C12 H12 . 0.9300
C13 C14 . 1.363(3)
C13 H13 . 0.9300
C14 C13 4_565 1.363(3)
C14 N2 . 1.469(5)
N1 H1A . 0.8993
N1 H1B . 0.8990
N1 H1C . 0.9005
N2 H2A . 0.8900
N2 H2B . 0.8900
N2 H2C . 0.8900
O1 H1D . 0.8217
O1 H1E . 0.8491
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
N2 H2C Cl1 4_675 0.89 2.70 3.253(3) 121.4
N2 H2C Cl1 2_746 0.89 2.53 3.252(3) 138.6
N2 H2B Cl1 1_645 0.89 2.41 3.253(3) 158.7
N2 H2A Cl1 3_766 0.89 2.46 3.252(3) 148.4
O1 H1E Cl1 3_666 0.85 2.42 3.183(3) 149.8
O1 H1D Cl1 2_646 0.82 2.38 3.183(3) 167.2
N1 H1C Cl1 1_644 0.90 2.22 3.101(3) 164.9
N1 H1B O1 1_554 0.90 1.78 2.678(6) 172.3
N1 H1A Cl1 4_674 0.90 2.23 3.101(3) 163.2
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_4
_geom_torsion
C6 C1 C2 C3 . . 0.0
C7 C1 C2 C3 . . 180.0
C1 C2 C3 C4 . . 0.0
C2 C3 C4 C5 . . 0.0
C2 C3 C4 N1 . . 180.0
C3 C4 C5 C6 . . 0.0
N1 C4 C5 C6 . . 180.0
C4 C5 C6 C1 . . 0.0
C2 C1 C6 C5 . . 0.0
C7 C1 C6 C5 . . 180.0
C2 C1 C7 C11 . . 0.0
C6 C1 C7 C11 . . 180.0
C2 C1 C7 C8 . . -121.3(2)
C6 C1 C7 C8 . . 58.7(2)
C2 C1 C7 C8 . 4_565 121.3(2)
C6 C1 C7 C8 . 4_565 -58.7(2)
C1 C7 C8 C9 . . -175.1(2)
C11 C7 C8 C9 . . 64.2(3)
C8 C7 C8 C9 4_565 . -56.7(4)
C7 C8 C9 C10 . . 56.5(3)
C8 C9 C10 C9 . 4_565 -53.9(5)
C1 C7 C11 C12 . 4_565 88.2(3)
C8 C7 C11 C12 . 4_565 -151.3(3)
C8 C7 C11 C12 4_565 4_565 -32.3(4)
C1 C7 C11 C12 . . -88.2(3)
C8 C7 C11 C12 . . 32.3(4)
C8 C7 C11 C12 4_565 . 151.3(3)
C12 C11 C12 C13 4_565 . -1.0(5)
C7 C11 C12 C13 . . 175.6(3)
C11 C12 C13 C14 . . 0.6(5)
C12 C13 C14 C13 . 4_565 -0.2(6)
C12 C13 C14 N2 . . -179.2(3)
