##############################################################################
#                                                                            #
# 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_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(4,6-Diamino-1,3-phenylene)bis(phenylmethanone)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H16 N2 O2'
_chemical_formula_sum     'C20 H16 N2 O2'
_chemical_formula_iupac     'C20 H16 N2 O2'
_chemical_formula_weight     316.35
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     13.602(3)
_cell_length_b     7.2350(14)
_cell_length_c     16.786(3)
_cell_angle_alpha     90.00
_cell_angle_beta     104.32(3)
_cell_angle_gamma     90.00
_cell_volume     1600.6(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     13
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.086
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.9747
_exptl_absorpt_correction_T_max     0.9915
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3034
_diffrn_reflns_av_R_equivalents     0.0501
_diffrn_reflns_av_sigmaI/netI     0.0402
_diffrn_reflns_theta_min     1.73
_diffrn_reflns_theta_max     25.26
_diffrn_reflns_theta_full     25.26
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     200
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1
_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     2905
_reflns_number_gt     1956
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0838
_refine_ls_R_factor_gt     0.0519
_refine_ls_wR_factor_gt     0.1372
_refine_ls_wR_factor_ref     0.1591
_refine_ls_goodness_of_fit_ref     1.002
_refine_ls_restrained_S_all     1.002
_refine_ls_number_reflns     2905
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0950P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.207
_refine_diff_density_min     -0.160
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef     0.033(4)
_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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 EXPRESS (Enraf--Nonius, 1985)'
_computing_cell_refinement     'CAD-4 EXPRESS (Enraf--Nonius, 1985)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 0.37312(16) 0.3893(3) 0.28367(12) 0.0591(6) Uani d . 1 1 . .
    H H1A 0.3491 0.4712 0.3109 0.071 Uiso calc R 1 1 . .
    H H1B 0.4341 0.3493 0.3021 0.071 Uiso calc R 1 1 . .
    O O1 0.52000(14) 0.1831(3) 0.24813(14) 0.0930(8) Uani d . 1 1 . .
    C C1 0.57390(17) -0.0458(4) 0.12198(14) 0.0531(6) Uani d . 1 1 . .
    H H1C 0.6095 0.0647 0.1245 0.064 Uiso calc R 1 1 . .
    O O2 0.04343(12) 0.1873(2) -0.05001(10) 0.0611(5) Uani d . 1 1 . .
    N N2 0.05679(14) 0.3923(3) 0.08577(13) 0.0578(6) Uani d . 1 1 . .
    H H2A 0.0370 0.4769 0.1142 0.069 Uiso calc R 1 1 . .
    H H2B 0.0163 0.3519 0.0415 0.069 Uiso calc R 1 1 . .
    C C2 0.60783(19) -0.2017(4) 0.08967(15) 0.0607(7) Uani d . 1 1 . .
    H H2C 0.6656 -0.1947 0.0696 0.073 Uiso calc R 1 1 . .
    C C3 0.5578(2) -0.3659(4) 0.08670(16) 0.0604(7) Uani d . 1 1 . .
    H H3A 0.5818 -0.4704 0.0653 0.072 Uiso calc R 1 1 . .
    C C4 0.4720(2) -0.3763(3) 0.11544(16) 0.0589(7) Uani d . 1 1 . .
    H H4A 0.4378 -0.4881 0.1138 0.071 Uiso calc R 1 1 . .
    C C5 0.43617(17) -0.2205(3) 0.14694(14) 0.0477(6) Uani d . 1 1 . .
    H H5A 0.3775 -0.2280 0.1658 0.057 Uiso calc R 1 1 . .
    C C6 0.48687(15) -0.0536(3) 0.15059(12) 0.0382(5) Uani d . 1 1 . .
    C C7 0.45547(17) 0.1125(3) 0.19187(14) 0.0468(6) Uani d . 1 1 . .
    C C8 0.35224(15) 0.1836(3) 0.16598(12) 0.0348(5) Uani d . 1 1 . .
    C C9 0.28558(14) 0.1203(3) 0.09414(12) 0.0333(5) Uani d . 1 1 . .
    H H9A 0.3095 0.0308 0.0639 0.040 Uiso calc R 1 1 . .
    C C10 0.18605(15) 0.1806(3) 0.06417(12) 0.0348(5) Uani d . 1 1 . .
    C C11 0.15099(16) 0.3230(3) 0.11055(13) 0.0399(5) Uani d . 1 1 . .
    C C12 0.21684(16) 0.3878(3) 0.18220(13) 0.0431(6) Uani d . 1 1 . .
    H H12A 0.1936 0.4795 0.2118 0.052 Uiso calc R 1 1 . .
    C C13 0.31502(16) 0.3235(3) 0.21194(12) 0.0395(5) Uani d . 1 1 . .
    C C14 0.12288(16) 0.1100(3) -0.01357(13) 0.0402(5) Uani d . 1 1 . .
    C C15 0.15422(15) -0.0590(3) -0.05239(12) 0.0384(5) Uani d . 1 1 . .
    C C16 0.18537(17) -0.2215(3) -0.00953(14) 0.0443(6) Uani d . 1 1 . .
    H H16A 0.1921 -0.2251 0.0469 0.053 Uiso calc R 1 1 . .
    C C17 0.20657(18) -0.3783(3) -0.04972(17) 0.0562(7) Uani d . 1 1 . .
    H H17A 0.2271 -0.4864 -0.0203 0.067 Uiso calc R 1 1 . .
    C C18 0.19713(19) -0.3735(4) -0.13331(18) 0.0642(8) Uani d . 1 1 . .
    H H18A 0.2113 -0.4785 -0.1604 0.077 Uiso calc R 1 1 . .
    C C19 0.1668(2) -0.2136(4) -0.17665(16) 0.0621(7) Uani d . 1 1 . .
    H H19A 0.1614 -0.2104 -0.2330 0.075 Uiso calc R 1 1 . .
    C C20 0.14434(17) -0.0577(4) -0.13704(14) 0.0523(6) Uani d . 1 1 . .
    H H20A 0.1224 0.0489 -0.1671 0.063 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 C13 . 1.353(3) ?
    N1 H1A . 0.8600 ?
    N1 H1B . 0.8600 ?
    O1 C7 . 1.230(3) ?
    C1 C2 . 1.380(3) ?
    C1 C6 . 1.384(3) ?
    C1 H1C . 0.9300 ?
    O2 C14 . 1.236(2) ?
    N2 C11 . 1.342(3) ?
    N2 H2A . 0.8600 ?
    N2 H2B . 0.8600 ?
    C2 C3 . 1.364(4) ?
    C2 H2C . 0.9300 ?
    C3 C4 . 1.371(4) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.384(3) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.384(3) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.501(3) ?
    C7 C8 . 1.457(3) ?
    C8 C9 . 1.395(3) ?
    C8 C13 . 1.439(3) ?
    C9 C10 . 1.392(3) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.442(3) ?
    C10 C14 . 1.465(3) ?
    C11 C12 . 1.391(3) ?
    C12 C13 . 1.385(3) ?
    C12 H12A . 0.9300 ?
    C14 C15 . 1.496(3) ?
    C15 C16 . 1.389(3) ?
    C15 C20 . 1.394(3) ?
    C16 C17 . 1.386(3) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.378(4) ?
    C17 H17A . 0.9300 ?
    C18 C19 . 1.374(4) ?
    C18 H18A . 0.9300 ?
    C19 C20 . 1.381(3) ?
    C19 H19A . 0.9300 ?
    C20 H20A . 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
    C13 N1 H1A . . 120.0 ?
    C13 N1 H1B . . 120.0 ?
    H1A N1 H1B . . 120.0 ?
    C2 C1 C6 . . 120.1(2) ?
    C2 C1 H1C . . 120.0 ?
    C6 C1 H1C . . 120.0 ?
    C11 N2 H2A . . 120.0 ?
    C11 N2 H2B . . 120.0 ?
    H2A N2 H2B . . 120.0 ?
    C3 C2 C1 . . 120.9(2) ?
    C3 C2 H2C . . 119.5 ?
    C1 C2 H2C . . 119.5 ?
    C2 C3 C4 . . 119.7(2) ?
    C2 C3 H3A . . 120.2 ?
    C4 C3 H3A . . 120.2 ?
    C3 C4 C5 . . 120.1(2) ?
    C3 C4 H4A . . 120.0 ?
    C5 C4 H4A . . 120.0 ?
    C4 C5 C6 . . 120.6(2) ?
    C4 C5 H5A . . 119.7 ?
    C6 C5 H5A . . 119.7 ?
    C5 C6 C1 . . 118.7(2) ?
    C5 C6 C7 . . 121.5(2) ?
    C1 C6 C7 . . 119.5(2) ?
    O1 C7 C8 . . 122.3(2) ?
    O1 C7 C6 . . 117.2(2) ?
    C8 C7 C6 . . 120.56(18) ?
    C9 C8 C13 . . 117.07(18) ?
    C9 C8 C7 . . 120.94(19) ?
    C13 C8 C7 . . 121.98(18) ?
    C10 C9 C8 . . 125.14(19) ?
    C10 C9 H9A . . 117.4 ?
    C8 C9 H9A . . 117.4 ?
    C9 C10 C11 . . 116.78(18) ?
    C9 C10 C14 . . 121.08(19) ?
    C11 C10 C14 . . 122.04(18) ?
    N2 C11 C12 . . 120.2(2) ?
    N2 C11 C10 . . 121.1(2) ?
    C12 C11 C10 . . 118.65(19) ?
    C13 C12 C11 . . 123.7(2) ?
    C13 C12 H12A . . 118.1 ?
    C11 C12 H12A . . 118.1 ?
    N1 C13 C12 . . 120.1(2) ?
    N1 C13 C8 . . 121.3(2) ?
    C12 C13 C8 . . 118.60(18) ?
    O2 C14 C10 . . 122.1(2) ?
    O2 C14 C15 . . 117.56(18) ?
    C10 C14 C15 . . 120.34(18) ?
    C16 C15 C20 . . 118.3(2) ?
    C16 C15 C14 . . 123.33(19) ?
    C20 C15 C14 . . 118.21(19) ?
    C17 C16 C15 . . 121.0(2) ?
    C17 C16 H16A . . 119.5 ?
    C15 C16 H16A . . 119.5 ?
    C18 C17 C16 . . 119.8(2) ?
    C18 C17 H17A . . 120.1 ?
    C16 C17 H17A . . 120.1 ?
    C19 C18 C17 . . 120.0(2) ?
    C19 C18 H18A . . 120.0 ?
    C17 C18 H18A . . 120.0 ?
    C18 C19 C20 . . 120.4(2) ?
    C18 C19 H19A . . 119.8 ?
    C20 C19 H19A . . 119.8 ?
    C19 C20 C15 . . 120.6(2) ?
    C19 C20 H20A . . 119.7 ?
    C15 C20 H20A . . 119.7 ?
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
    C6 C1 C2 C3 . . . . -1.2(4) ?
    C1 C2 C3 C4 . . . . 0.6(4) ?
    C2 C3 C4 C5 . . . . 0.3(4) ?
    C3 C4 C5 C6 . . . . -0.7(4) ?
    C4 C5 C6 C1 . . . . 0.1(3) ?
    C4 C5 C6 C7 . . . . -174.0(2) ?
    C2 C1 C6 C5 . . . . 0.8(3) ?
    C2 C1 C6 C7 . . . . 175.0(2) ?
    C5 C6 C7 O1 . . . . 122.8(3) ?
    C1 C6 C7 O1 . . . . -51.2(3) ?
    C5 C6 C7 C8 . . . . -56.6(3) ?
    C1 C6 C7 C8 . . . . 129.3(2) ?
    O1 C7 C8 C9 . . . . 169.7(2) ?
    C6 C7 C8 C9 . . . . -11.0(3) ?
    O1 C7 C8 C13 . . . . -9.2(4) ?
    C6 C7 C8 C13 . . . . 170.2(2) ?
    C13 C8 C9 C10 . . . . -0.7(3) ?
    C7 C8 C9 C10 . . . . -179.60(19) ?
    C8 C9 C10 C11 . . . . 1.7(3) ?
    C8 C9 C10 C14 . . . . 177.93(19) ?
    C9 C10 C11 N2 . . . . 178.84(19) ?
    C14 C10 C11 N2 . . . . 2.6(3) ?
    C9 C10 C11 C12 . . . . -1.4(3) ?
    C14 C10 C11 C12 . . . . -177.56(19) ?
    N2 C11 C12 C13 . . . . 179.9(2) ?
    C10 C11 C12 C13 . . . . 0.1(3) ?
    C11 C12 C13 N1 . . . . -177.7(2) ?
    C11 C12 C13 C8 . . . . 0.9(3) ?
    C9 C8 C13 N1 . . . . 177.98(19) ?
    C7 C8 C13 N1 . . . . -3.1(3) ?
    C9 C8 C13 C12 . . . . -0.6(3) ?
    C7 C8 C13 C12 . . . . 178.3(2) ?
    C9 C10 C14 O2 . . . . -164.4(2) ?
    C11 C10 C14 O2 . . . . 11.6(3) ?
    C9 C10 C14 C15 . . . . 14.6(3) ?
    C11 C10 C14 C15 . . . . -169.40(18) ?
    O2 C14 C15 C16 . . . . -132.7(2) ?
    C10 C14 C15 C16 . . . . 48.2(3) ?
    O2 C14 C15 C20 . . . . 42.3(3) ?
    C10 C14 C15 C20 . . . . -136.8(2) ?
    C20 C15 C16 C17 . . . . 0.3(3) ?
    C14 C15 C16 C17 . . . . 175.3(2) ?
    C15 C16 C17 C18 . . . . 0.3(4) ?
    C16 C17 C18 C19 . . . . 0.0(4) ?
    C17 C18 C19 C20 . . . . -0.9(4) ?
    C18 C19 C20 C15 . . . . 1.4(4) ?
    C16 C15 C20 C19 . . . . -1.1(3) ?
    C14 C15 C20 C19 . . . . -176.4(2) ?
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 H1B O1 . 0.86 2.04 2.676(3) 130 yes
    N2 H2B O2 . 0.86 2.05 2.688(3) 131 yes
    C19 H19A Cg1 4_555 0.93 2.79 3.555(3) 140 yes
    N1 H1A Cg2 2_555 0.86 2.71 3.550(2) 167 yes
data_TDM
_journal_date_recd_electronic     2011-08-02
_journal_date_accepted     2011-08-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     10
_journal_page_first     o2619
_journal_page_last     o2619
_journal_paper_category     QO
_journal_coeditor_code     VM2115
_publ_contact_author_name     'Professor Da-Min Tian'
_publ_contact_author_address
;
'Da-Min Tian'
Department of Chemistry and Chemical Engineering
Henan University of Urban
Henan 467036
P.R. China
;
_publ_contact_author_email     'tiandamin2009@163.com'
_publ_contact_author_fax     '86-375-2089043'
_publ_contact_author_phone     '86-375-2089043'
_publ_section_title
;
(4,6-Diamino-1,3-phenylene)bis(phenylmethanone)
;
loop_
    _publ_author_name
    _publ_author_address
    'Da-Min Tian'
;
Department of Chemistry and Chemical Engineering
Henan University of Urban
Henan 467036
People's Republic of China
;
    'Hui Xu'
;
Department of Chemistry and Chemical Engineering
Henan University of Urban
Henan 467036
People's Republic of China
;
