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#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239138.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2239138
loop_
_publ_author_name
'Al-Fahdawi, Aeed S.'
'Al-Kafajy, Hussain A.'
'Al-Jeboori, Mohamad J.'
'Coles, Simon J.'
'Wilson, Claire'
'Potgieter, Herman'
_publ_section_title
;
 N,N'-Bis(diphenylmethyl)benzene-1,4-diamine
;
_journal_coeditor_code           HB7158
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o66
_journal_paper_doi               10.1107/S1600536813033497
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C32 H28 N2'
_chemical_formula_moiety         'C32 H28 N2'
_chemical_formula_sum            'C32 H28 N2'
_chemical_formula_weight         440.56
_chemical_name_systematic
;
N,N'-Bis(diphenylmethyl)benzene-1,4-diamine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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     dual
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 107.914(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.784(2)
_cell_length_b                   5.5853(8)
_cell_length_c                   14.896(2)
_cell_measurement_reflns_used    5636
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.4
_cell_volume                     1170.4(3)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXD (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1248
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10305
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.40
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrystalClear-SM Expert; Rigaku, 2012)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.294
_refine_ls_extinction_coef       0.026(5)
_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   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.1678
_refine_ls_R_factor_gt           0.0768
_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)+(0.0886P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1671
_refine_ls_wR_factor_ref         0.2078
_reflns_number_gt                1254
_reflns_number_total             2664
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7158sup1.cif
_cod_data_source_block           I
_cod_database_code               2239138
_cod_database_fobs_code          2239138
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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
_atom_site_symmetry_multiplicity
N N1 0.44891(16) 0.4954(4) 0.1672(2) 0.0366(7) Uani d . 1 1
H H1 0.4144 0.6110 0.1765 0.044 Uiso calc R 1 1
C C2 0.47809(19) 0.3103(5) 0.2375(2) 0.0294(8) Uani d . 1 1
H H2 0.4635 0.1559 0.2050 0.035 Uiso calc R 1 1
C C3 0.58440(19) 0.3135(5) 0.2909(2) 0.0273(7) Uani d . 1 1
C C4 0.6426(2) 0.5024(5) 0.2829(2) 0.0295(8) Uani d . 1 1
H H4 0.6169 0.6316 0.2440 0.035 Uiso calc R 1 1
C C5 0.7386(2) 0.4993(5) 0.3323(2) 0.0314(8) Uani d . 1 1
H H5 0.7768 0.6270 0.3265 0.038 Uiso calc R 1 1
C C6 0.7785(2) 0.3094(5) 0.3901(2) 0.0326(8) Uani d . 1 1
H H6 0.8431 0.3080 0.4231 0.039 Uiso calc R 1 1
C C7 0.7208(2) 0.1209(5) 0.3983(2) 0.0329(8) Uani d . 1 1
H H7 0.7468 -0.0081 0.4371 0.039 Uiso calc R 1 1
C C8 0.6248(2) 0.1228(5) 0.3492(2) 0.0325(8) Uani d . 1 1
H H8 0.5868 -0.0051 0.3554 0.039 Uiso calc R 1 1
C C9 0.41899(19) 0.3290(5) 0.3050(2) 0.0303(8) Uani d . 1 1
C C10 0.4294(2) 0.5250(5) 0.3644(3) 0.0392(9) Uani d . 1 1
H H10 0.4723 0.6451 0.3626 0.047 Uiso calc R 1 1
C C11 0.3771(2) 0.5438(6) 0.4259(3) 0.0433(9) Uani d . 1 1
H H11 0.3845 0.6767 0.4651 0.052 Uiso calc R 1 1
C C12 0.3137(2) 0.3662(6) 0.4296(3) 0.0416(9) Uani d . 1 1
H H12 0.2782 0.3785 0.4712 0.050 Uiso calc R 1 1
C C13 0.3032(2) 0.1706(6) 0.3712(3) 0.0421(10) Uani d . 1 1
H H13 0.2614 0.0487 0.3742 0.051 Uiso calc R 1 1
C C14 0.3545(2) 0.1546(5) 0.3081(3) 0.0386(9) Uani d . 1 1
H H14 0.3454 0.0245 0.2673 0.046 Uiso calc R 1 1
C C15 0.47494(18) 0.4941(5) 0.0834(2) 0.0283(8) Uani d . 1 1
C C16 0.5290(2) 0.3109(5) 0.0627(2) 0.0315(8) Uani d . 1 1
H H16 0.5489 0.1834 0.1042 0.038 Uiso calc R 1 1
C C17 0.44676(19) 0.6813(5) 0.0199(2) 0.0294(8) Uani d . 1 1
H H17 0.4107 0.8049 0.0332 0.035 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'
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
C2 N1 H1 . 118.8
C15 N1 H1 . 118.8
C15 N1 C2 . 122.4(2)
N1 C2 H2 . 107.6
N1 C2 C3 . 113.6(2)
N1 C2 C9 . 109.0(2)
C3 C2 H2 . 107.6
C9 C2 H2 . 107.6
C9 C2 C3 . 111.2(3)
C4 C3 C2 . 121.9(3)
C8 C3 C2 . 119.5(2)
C8 C3 C4 . 118.6(3)
C3 C4 H4 . 119.8
C5 C4 C3 . 120.4(3)
C5 C4 H4 . 119.8
C4 C5 H5 . 119.6
C6 C5 C4 . 120.9(3)
C6 C5 H5 . 119.6
C5 C6 H6 . 120.6
C5 C6 C7 . 118.9(3)
C7 C6 H6 . 120.6
C6 C7 H7 . 119.7
C8 C7 C6 . 120.6(3)
C8 C7 H7 . 119.7
C3 C8 H8 . 119.7
C7 C8 C3 . 120.7(3)
C7 C8 H8 . 119.7
C10 C9 C2 . 120.1(2)
C14 C9 C2 . 121.2(3)
C14 C9 C10 . 118.7(3)
C9 C10 H10 . 119.6
C11 C10 C9 . 120.8(3)
C11 C10 H10 . 119.6
C10 C11 H11 . 120.0
C10 C11 C12 . 120.1(3)
C12 C11 H11 . 120.0
C11 C12 H12 . 120.3
C13 C12 C11 . 119.5(3)
C13 C12 H12 . 120.3
C12 C13 H13 . 119.9
C12 C13 C14 . 120.3(3)
C14 C13 H13 . 119.9
C9 C14 C13 . 120.6(3)
C9 C14 H14 . 119.7
C13 C14 H14 . 119.7
C16 C15 N1 . 122.1(3)
C17 C15 N1 . 119.5(3)
C17 C15 C16 . 118.5(3)
C15 C16 H16 . 120.1
C17 C16 C15 3_665 119.9(3)
C17 C16 H16 3_665 120.1
C15 C17 H17 . 119.2
C16 C17 C15 3_665 121.7(3)
C16 C17 H17 3_665 119.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
N1 H1 . 0.8600
N1 C2 . 1.440(4)
N1 C15 . 1.415(4)
C2 H2 . 0.9800
C2 C3 . 1.528(4)
C2 C9 . 1.525(4)
C3 C4 . 1.389(4)
C3 C8 . 1.388(4)
C4 H4 . 0.9300
C4 C5 . 1.384(4)
C5 H5 . 0.9300
C5 C6 . 1.379(4)
C6 H6 . 0.9300
C6 C7 . 1.384(4)
C7 H7 . 0.9300
C7 C8 . 1.382(4)
C8 H8 . 0.9300
C9 C10 . 1.386(4)
C9 C14 . 1.373(4)
C10 H10 . 0.9300
C10 C11 . 1.372(4)
C11 H11 . 0.9300
C11 C12 . 1.378(4)
C12 H12 . 0.9300
C12 C13 . 1.375(5)
C13 H13 . 0.9300
C13 C14 . 1.380(4)
C14 H14 . 0.9300
C15 C16 . 1.391(4)
C15 C17 . 1.385(4)
C16 H16 . 0.9300
C16 C17 3_665 1.384(4)
C17 C16 3_665 1.384(4)
C17 H17 . 0.9300
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_4
_geom_torsion
N1 C2 C3 C4 . 10.4(4)
N1 C2 C3 C8 . -169.4(3)
N1 C2 C9 C10 . -67.2(4)
N1 C2 C9 C14 . 112.5(3)
N1 C15 C16 C17 3_665 -179.5(3)
N1 C15 C17 C16 3_665 179.5(3)
C2 N1 C15 C16 . 1.3(4)
C2 N1 C15 C17 . -178.1(3)
C2 C3 C4 C5 . -180.0(3)
C2 C3 C8 C7 . 179.9(3)
C2 C9 C10 C11 . -179.7(3)
C2 C9 C14 C13 . 178.4(3)
C3 C2 C9 C10 . 58.8(4)
C3 C2 C9 C14 . -121.5(3)
C3 C4 C5 C6 . 0.2(5)
C4 C3 C8 C7 . 0.1(4)
C4 C5 C6 C7 . -0.2(5)
C5 C6 C7 C8 . 0.1(4)
C6 C7 C8 C3 . 0.0(5)
C8 C3 C4 C5 . -0.1(4)
C9 C2 C3 C4 . -113.0(3)
C9 C2 C3 C8 . 67.2(3)
C9 C10 C11 C12 . 0.4(5)
C10 C9 C14 C13 . -1.9(5)
C10 C11 C12 C13 . 0.0(5)
C11 C12 C13 C14 . -1.3(5)
C12 C13 C14 C9 . 2.3(5)
C14 C9 C10 C11 . 0.6(5)
C15 N1 C2 C3 . 69.6(3)
C15 N1 C2 C9 . -165.8(2)
C16 C15 C17 C16 3_665 0.1(5)
C17 C15 C16 C17 3_665 -0.1(4)
