##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2013-11-04
_journal_date_accepted     2013-12-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      1
_journal_page_first     o66
_journal_page_last     o66
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813033497
_journal_coeditor_code     HB7158
_publ_contact_author_name     'Mr. Aeed Al-Fahdawi'
_publ_contact_author_address
;
Department of Chemistry,
College of Science,
University of Babylon,
Iraq
;
_publ_contact_author_email     'aeedchemistry@yahoo.co.uk'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
N,N'-Bis(diphenylmethyl)benzene-1,4-diamine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Al-Fahdawi, Aeed S.' .
;
Department of Chemistry, College of Science, University of Babylon, Iraq
;
    'Al-Kafajy, Hussain A.' .
;
Department of Chemistry, College of Science, University of Babylon, Iraq
;
    'Al-Jeboori, Mohamad J.' .
;
Department of Chemical Engineering and Chemical Technology,
Imperial College London, London SW7 2AZ, England
;
    'Coles, Simon J.' .
;
UK National Crystallography Service
Chemistry
Faculty of Natural and Environmental Sciences
University of Southampton
Southampton
SO17 1BJ
England
;
    'Wilson, Claire' .
;
Diamond Light Source
Harwell Science and Innovation Campus
Didcot
Oxfordshire OX11 0DE
England
;
    'Potgieter, Herman' .
;
School of Research, Enterprise and Innovation,
Manchester Metropolitan University
Chester Street
Manchester M1 5GD
England
;
data_I
_database_code_depnum_ccdc_archive 'CCDC 976380'
_chemical_name_systematic
;
N,N'-Bis(diphenylmethyl)benzene-1,4-diamine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C32 H28 N2'
_chemical_formula_sum     'C32 H28 N2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C32 H28 N2'
_chemical_formula_weight     440.56
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/n'
_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     14.784(2)
_cell_length_b     5.5853(8)
_cell_length_c     14.896(2)
_cell_angle_alpha     90.00
_cell_angle_beta     107.914(8)
_cell_angle_gamma     90.00
_cell_volume     1170.4(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     5636
_cell_measurement_theta_min     3.4
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     100
_exptl_crystal_description     Plate
_exptl_crystal_colour     Colourless
_exptl_crystal_size_max     0.1
_exptl_crystal_size_mid     0.09
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.250
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     468
_exptl_absorpt_coefficient_mu     0.073
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrystalClear-SM Expert; Rigaku, 2012)
;
_exptl_absorpt_correction_T_min     0.345
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
FT---IR data were recorded on a Nicolet ATR FT---IR, while NMR data were
collected on a Bruker 400 MHz s pectrometer in CD₂Cl₂-- d2 solutions. The
assignment of the chemical shifts for the NMR data were made following
numbering shown in structure B. Schiff-base
{N1,N4-bis(diphenylmethylene)benzene-1,4-diamine}
IR (ATR cm-1) 1620 (C=N), 1597 and 1570 (phenyl). NMR data (p.p.m.), \dH (400
MHz, CD2Cl2): 6.47 (4H, m; C3, 3`, 11, 11`-H), 7.06 (2H, d, J =
7.33 Hz; C15, 15`-H), 7.73 (2H, d, J = 7.33 Hz; C16, 16`-H), 7.27--7.40
(20H, m; aromatic-H); \dC (100.63 MHz, CD2Cl2): 121.53--136.75,
(aromatic carbon); 140.12 (C6, 6`,8, 8`); 147.37 (C14, 14`); 168.24 (C7, 7`);
DEPT 13 C NMR exhibited no signals between 140--170 p.p.m.. The positive ES
mass spectrum of the bis-amine showed the parent ion peak at m/z =
441.2362 (M+H)+ (95%) corresponding to C32H28N2; required value =
440.2252. Peaks detected at m/z =247.16 (100%) and 167.09 (98%),
correspond to [M-(ph)2CH2)]+ and [M-(ph)2CH2+H2N2ph)]+,
respectively.
bis-amine {N1,N4-dibenzhydrylbenzene-1,4-diamine IR (ATR cm-1): 3392 (N---H),
2932; 2873 (C---H) aliphatic, 1599 and 1510 (phenyl). NMR data (p.p.m.), \dH
(400 MHz, CD2Cl2): 3.95 (2H, S, Na, a`-H), 5.36 (2H, S; C7,
7`-H), 6.37 (4H, d, J=7.33 Hz; C15, 15`, 16, 16`-H), 7.21--7.36
(20H, m, Ar---H); \dC (100.63 MHz, CD2Cl2): 49.10 (C7, 7`); 115.21
(C15, 15`, 16, 16`); 127.25--129.04 (aromatic carbon); 140 (C6, 6`, 8, 8`);
144.07 (C14, 14`), DEPT 13 C NMR exhibited no signals between 140--145 p.p.m..
The positive ES mass spectrum of the bis-amine showed the parent ion peak at
m/z = 441.2362 (M+H)+ (95%) corresponding to C32H28N2; required
value = 440.2252. Peaks detected at m/z =247.16 (100%) and 167.09
(98%), correspond to [M-(ph)2CH2)]+ and [M-(ph)2CH2+H2N2ph)]+,
respectively.
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_monochromator     Confocal
_diffrn_measurement_device_type     'Rigaku AFC12 (Right)'
_diffrn_measurement_device     'four-circle κ goniometer'
_diffrn_measurement_method     'profile data from ω-scans'
_diffrn_detector_area_resol_mean     28.5714
_diffrn_reflns_number     10305
_diffrn_reflns_av_R_equivalents     0.1248
_diffrn_reflns_theta_min     3.40
_diffrn_reflns_theta_max     27.48
_diffrn_reflns_theta_full     27.48
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -19
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2664
_reflns_number_gt     1254
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1678
_refine_ls_R_factor_gt     0.0768
_refine_ls_wR_factor_gt     0.1671
_refine_ls_wR_factor_ref     0.2078
_refine_ls_goodness_of_fit_ref     0.970
_refine_ls_restrained_S_all     0.970
_refine_ls_number_reflns     2664
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0886P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.330
_refine_diff_density_min     -0.294
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.026(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2012)
;
_computing_structure_solution
;
SHELXD (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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 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_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 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_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_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    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) ?
