#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/33/2233386.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_2233386
loop_
_publ_author_name
'Arvinnezhad, Hamid'
'Jadidi, Khosrow'
'Notash, Behrouz'
_publ_section_title
;
 (1R,2R,E,E)-N,N'-Bis(4-chlorobenzylidene)cyclohexane-1,2-diamine
;
_journal_coeditor_code           BT5777
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o407
_journal_page_last               o408
_journal_paper_doi               10.1107/S1600536812000724
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H20 Cl2 N2'
_chemical_formula_moiety         'C20 H20 Cl2 N2'
_chemical_formula_sum            'C20 H20 Cl2 N2'
_chemical_formula_weight         359.28
_chemical_name_systematic
;
(1R,2R,E,E)-N,N'-Bis(4-
chlorobenzylidene)cyclohexane-1,2-diamine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5058(11)
_cell_length_b                   15.734(3)
_cell_length_c                   21.302(4)
_cell_measurement_reflns_used    4973
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.19
_cell_measurement_theta_min      2.31
_cell_volume                     1845.4(6)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2005)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Stoe IPDS 2T'
_diffrn_measurement_method       'rotation method'
_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  0.0876
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12920
_diffrn_reflns_theta_full        29.19
_diffrn_reflns_theta_max         29.19
_diffrn_reflns_theta_min         2.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.337
_refine_ls_abs_structure_details 'Flack (1983), 2099 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.11(7)
_refine_ls_extinction_coef       0.0059(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4973
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0326P)²+0.5925P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1134
_reflns_number_gt                4065
_reflns_number_total             4973
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5777.cif
_cod_data_source_block           I
_cod_database_code               2233386
_cod_database_fobs_code          2233386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
Cl Cl1 -0.02567(12) 1.06658(5) 0.95529(3) 0.03732(17) Uani d . 1 1
Cl Cl2 1.02450(16) 0.61772(5) 1.03022(3) 0.0446(2) Uani d . 1 1
C C9 0.5215(5) 1.08153(16) 0.83309(11) 0.0302(5) Uani d . 1 1
H H9 0.6498 1.1182 0.8246 0.036 Uiso calc R 1 1
N N2 0.9823(4) 0.78245(13) 0.73687(9) 0.0292(5) Uani d . 1 1
C C3 1.0135(5) 0.91257(17) 0.56137(10) 0.0316(5) Uani d . 1 1
H H3A 0.9729 0.9310 0.5192 0.038 Uiso calc R 1 1
H H3B 1.1598 0.9422 0.5742 0.038 Uiso calc R 1 1
C C18 0.9686(5) 0.65212(16) 0.95383(11) 0.0333(6) Uani d . 1 1
N N1 0.6607(4) 0.92267(14) 0.71446(9) 0.0284(5) Uani d . 1 1
C C12 0.1355(5) 0.97300(18) 0.85723(11) 0.0293(5) Uani d . 1 1
H H12 0.0050 0.9371 0.8655 0.035 Uiso calc R 1 1
C C8 0.4930(5) 1.00840(15) 0.79711(10) 0.0258(5) Uani d . 1 1
C C10 0.3615(5) 1.10062(18) 0.88148(12) 0.0319(6) Uani d . 1 1
H H10 0.3825 1.1493 0.9057 0.038 Uiso calc R 1 1
C C7 0.6765(5) 0.98715(16) 0.74955(10) 0.0256(5) Uani d . 1 1
H H7 0.8102 1.0228 0.7451 0.031 Uiso calc R 1 1
C C14 0.8364(5) 0.73657(17) 0.76733(12) 0.0302(6) Uani d . 1 1
H H14 0.6916 0.7206 0.7482 0.036 Uiso calc R 1 1
C C11 0.1706(5) 1.04590(17) 0.89291(11) 0.0279(5) Uani d . 1 1
C C1 0.8652(5) 0.90495(16) 0.67300(11) 0.0269(5) Uani d . 1 1
H H1 1.0099 0.9347 0.6884 0.032 Uiso calc R 1 1
C C15 0.8846(5) 0.70693(17) 0.83196(12) 0.0301(6) Uani d . 1 1
C C2 0.8063(5) 0.93512(19) 0.60586(11) 0.0301(5) Uani d . 1 1
H H2A 0.6575 0.9083 0.5916 0.036 Uiso calc R 1 1
H H2B 0.7814 0.9962 0.6058 0.036 Uiso calc R 1 1
C C17 1.1362(6) 0.70438(18) 0.92486(12) 0.0339(6) Uani d . 1 1
H H17 1.2761 0.7210 0.9460 0.041 Uiso calc R 1 1
C C13 0.2957(5) 0.95433(17) 0.80948(11) 0.0285(6) Uani d . 1 1
H H13 0.2732 0.9057 0.7854 0.034 Uiso calc R 1 1
C C4 1.0598(6) 0.81726(19) 0.56146(11) 0.0366(6) Uani d . 1 1
H H4A 1.1963 0.8045 0.5343 0.044 Uiso calc R 1 1
H H4B 0.9183 0.7880 0.5451 0.044 Uiso calc R 1 1
C C5 1.1139(6) 0.78524(18) 0.62769(12) 0.0349(6) Uani d . 1 1
H H5A 1.1323 0.7239 0.6268 0.042 Uiso calc R 1 1
H H5B 1.2658 0.8096 0.6421 0.042 Uiso calc R 1 1
C C6 0.9115(5) 0.80889(17) 0.67350(11) 0.0292(6) Uani d . 1 1
H H6 0.7621 0.7792 0.6615 0.035 Uiso calc R 1 1
C C19 0.7602(5) 0.6264(2) 0.92339(13) 0.0382(7) Uani d . 1 1
H H19 0.6486 0.5912 0.9433 0.046 Uiso calc R 1 1
C C16 1.0941(5) 0.73191(17) 0.86384(12) 0.0328(6) Uani d . 1 1
H H16 1.2062 0.7672 0.8441 0.039 Uiso calc R 1 1
C C20 0.7205(5) 0.65407(19) 0.86231(13) 0.0372(6) Uani d . 1 1
H H20 0.5809 0.6368 0.8413 0.045 Uiso calc R 1 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'
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
C10 C9 C8 121.1(3)
C10 C9 H9 119.5
C8 C9 H9 119.5
C14 N2 C6 117.9(2)
C4 C3 C2 110.7(2)
C4 C3 H3A 109.5
C2 C3 H3A 109.5
C4 C3 H3B 109.5
C2 C3 H3B 109.5
H3A C3 H3B 108.1
C19 C18 C17 121.4(2)
C19 C18 Cl2 119.7(2)
C17 C18 Cl2 119.0(2)
C7 N1 C1 117.3(2)
C13 C12 C11 119.4(3)
C13 C12 H12 120.3
C11 C12 H12 120.3
C9 C8 C13 119.0(2)
C9 C8 C7 119.4(2)
C13 C8 C7 121.5(2)
C11 C10 C9 118.6(2)
C11 C10 H10 120.7
C9 C10 H10 120.7
N1 C7 C8 122.9(2)
N1 C7 H7 118.5
C8 C7 H7 118.5
N2 C14 C15 123.1(3)
N2 C14 H14 118.4
C15 C14 H14 118.4
C10 C11 C12 121.6(2)
C10 C11 Cl1 119.3(2)
C12 C11 Cl1 119.0(2)
N1 C1 C6 108.2(2)
N1 C1 C2 109.9(2)
C6 C1 C2 110.2(2)
N1 C1 H1 109.5
C6 C1 H1 109.5
C2 C1 H1 109.5
C20 C15 C16 118.7(2)
C20 C15 C14 120.4(3)
C16 C15 C14 120.9(2)
C3 C2 C1 110.3(2)
C3 C2 H2A 109.6
C1 C2 H2A 109.6
C3 C2 H2B 109.6
C1 C2 H2B 109.6
H2A C2 H2B 108.1
C18 C17 C16 119.5(3)
C18 C17 H17 120.3
C16 C17 H17 120.3
C12 C13 C8 120.3(2)
C12 C13 H13 119.9
C8 C13 H13 119.9
C3 C4 C5 111.0(2)
C3 C4 H4A 109.4
C5 C4 H4A 109.4
C3 C4 H4B 109.4
C5 C4 H4B 109.4
H4A C4 H4B 108.0
C6 C5 C4 111.6(2)
C6 C5 H5A 109.3
C4 C5 H5A 109.3
C6 C5 H5B 109.3
C4 C5 H5B 109.3
H5A C5 H5B 108.0
N2 C6 C5 109.0(2)
N2 C6 C1 109.3(2)
C5 C6 C1 110.9(2)
N2 C6 H6 109.2
C5 C6 H6 109.2
C1 C6 H6 109.2
C18 C19 C20 118.6(3)
C18 C19 H19 120.7
C20 C19 H19 120.7
C17 C16 C15 120.4(3)
C17 C16 H16 119.8
C15 C16 H16 119.8
C15 C20 C19 121.5(3)
C15 C20 H20 119.3
C19 C20 H20 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.743(3)
Cl2 C18 1.742(2)
C9 C10 1.389(4)
C9 C8 1.391(3)
C9 H9 0.9300
N2 C14 1.260(3)
N2 C6 1.466(3)
C3 C4 1.521(4)
C3 C2 1.525(3)
C3 H3A 0.9700
C3 H3B 0.9700
C18 C19 1.379(4)
C18 C17 1.382(4)
N1 C7 1.263(3)
N1 C1 1.458(3)
C12 C13 1.378(4)
C12 C11 1.389(4)
C12 H12 0.9300
C8 C13 1.404(4)
C8 C7 1.469(3)
C10 C11 1.380(4)
C10 H10 0.9300
C7 H7 0.9300
C14 C15 1.478(4)
C14 H14 0.9300
C1 C6 1.533(4)
C1 C2 1.541(3)
C1 H1 0.9800
C15 C20 1.388(4)
C15 C16 1.395(4)
C2 H2A 0.9700
C2 H2B 0.9700
C17 C16 1.390(3)
C17 H17 0.9300
C13 H13 0.9300
C4 C5 1.527(4)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.527(4)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6 0.9800
C19 C20 1.390(4)
C19 H19 0.9300
C16 H16 0.9300
C20 H20 0.9300
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
C3 H3A Cl1 2_574 0.97 2.81 3.525(3) 130.8 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
C10 C9 C8 C13 1.3(4)
C10 C9 C8 C7 -175.4(2)
C8 C9 C10 C11 -0.7(4)
C1 N1 C7 C8 -174.9(2)
C9 C8 C7 N1 -178.8(2)
C13 C8 C7 N1 4.6(4)
C6 N2 C14 C15 -178.9(2)
C9 C10 C11 C12 -0.2(4)
C9 C10 C11 Cl1 177.6(2)
C13 C12 C11 C10 0.5(4)
C13 C12 C11 Cl1 -177.32(19)
C7 N1 C1 C6 138.6(2)
C7 N1 C1 C2 -101.0(3)
N2 C14 C15 C20 -177.8(3)
N2 C14 C15 C16 2.7(4)
C4 C3 C2 C1 58.1(3)
N1 C1 C2 C3 -176.9(2)
C6 C1 C2 C3 -57.8(3)
C19 C18 C17 C16 0.2(4)
Cl2 C18 C17 C16 179.7(2)
C11 C12 C13 C8 0.1(4)
C9 C8 C13 C12 -1.0(4)
C7 C8 C13 C12 175.6(2)
C2 C3 C4 C5 -56.8(3)
C3 C4 C5 C6 55.3(3)
C14 N2 C6 C5 -127.0(3)
C14 N2 C6 C1 111.7(3)
C4 C5 C6 N2 -175.6(2)
C4 C5 C6 C1 -55.2(3)
N1 C1 C6 N2 -63.4(3)
C2 C1 C6 N2 176.4(2)
N1 C1 C6 C5 176.4(2)
C2 C1 C6 C5 56.2(3)
C17 C18 C19 C20 0.0(4)
Cl2 C18 C19 C20 -179.5(2)
C18 C17 C16 C15 -0.1(4)
C20 C15 C16 C17 -0.2(4)
C14 C15 C16 C17 179.3(3)
C16 C15 C20 C19 0.4(4)
C14 C15 C20 C19 -179.1(3)
C18 C19 C20 C15 -0.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9648669
