#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230229.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_2230229
loop_
_publ_author_name
'Shakuntala, K.'
'Foro, Sabine'
'Gowda, B. Thimme'
_publ_section_title
;
 N,N'-Bis(4-chlorophenyl)maleamide
;
_journal_coeditor_code           BQ2300
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1415
_journal_paper_doi               10.1107/S1600536811017636
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H12 Cl2 N2 O2'
_chemical_formula_moiety         'C16 H12 Cl2 N2 O2'
_chemical_formula_sum            'C16 H12 Cl2 N2 O2'
_chemical_formula_weight         335.18
_chemical_name_common
;
N,N'-Bis(4-chlorophenyl)maleamide
;
_chemical_name_systematic
;
N,N'-bis(4-chlorophenyl)but-2-enediamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.916(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2397(7)
_cell_length_b                   13.0154(8)
_cell_length_c                   13.1239(9)
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.80
_cell_volume                     1501.73(19)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer
with a Sapphire CCD detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using 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  0.0112
_diffrn_reflns_av_sigmaI/netI    0.0147
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6063
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.80
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.8720
_exptl_absorpt_correction_T_min  0.8300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            'dark grey'
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.244
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3065
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.3163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0908
_reflns_number_gt                2523
_reflns_number_total             3065
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2300.cif
_cod_data_source_block           I
_cod_original_cell_volume        1501.73(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2230229
_cod_database_fobs_code          2230229
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'
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
Cl Cl1 1.02985(5) -0.18771(4) 0.07433(4) 0.05576(15) Uani d . 1 1 . .
Cl Cl2 0.34374(6) 0.72529(3) -0.01488(4) 0.06130(16) Uani d . 1 1 . .
O O1 0.49648(15) 0.13865(8) 0.14544(12) 0.0566(4) Uani d . 1 1 . .
O O2 0.10969(14) 0.32142(8) 0.19093(9) 0.0449(3) Uani d . 1 1 . .
N N1 0.49484(15) -0.03027(10) 0.18426(11) 0.0380(3) Uani d D 1 1 . .
H H1N 0.4540(19) -0.0748(13) 0.2131(13) 0.046 Uiso d D 1 1 . .
N N2 0.30826(16) 0.29745(10) 0.12704(11) 0.0393(3) Uani d D 1 1 . .
H H2N 0.3780(18) 0.2545(14) 0.1250(14) 0.047 Uiso d D 1 1 . .
C C1 0.62405(17) -0.06341(11) 0.15703(12) 0.0349(3) Uani d . 1 1 . .
C C2 0.7035(2) -0.00167(13) 0.10578(14) 0.0479(4) Uani d . 1 1 . .
H H2 0.6734 0.0660 0.0888 0.057 Uiso calc R 1 1 . .
C C3 0.8268(2) -0.04074(14) 0.08021(14) 0.0479(4) Uani d . 1 1 . .
H H3 0.8799 0.0007 0.0462 0.057 Uiso calc R 1 1 . .
C C4 0.87128(18) -0.14080(13) 0.10489(12) 0.0399(4) Uani d . 1 1 . .
C C5 0.79395(19) -0.20323(12) 0.15518(13) 0.0430(4) Uani d . 1 1 . .
H H5 0.8240 -0.2711 0.1711 0.052 Uiso calc R 1 1 . .
C C6 0.67118(18) -0.16405(11) 0.18174(13) 0.0391(3) Uani d . 1 1 . .
H H6 0.6196 -0.2057 0.2166 0.047 Uiso calc R 1 1 . .
C C7 0.43672(17) 0.06548(11) 0.17594(12) 0.0367(3) Uani d . 1 1 . .
C C8 0.29546(19) 0.07352(12) 0.20689(13) 0.0410(4) Uani d . 1 1 . .
H H8 0.2649 0.0130 0.2319 0.049 Uiso calc R 1 1 . .
C C9 0.20588(19) 0.15430(12) 0.20424(13) 0.0423(4) Uani d . 1 1 . .
H H9 0.1231 0.1380 0.2274 0.051 Uiso calc R 1 1 . .
C C10 0.20609(17) 0.26486(11) 0.17309(11) 0.0346(3) Uani d . 1 1 . .
C C11 0.31503(17) 0.40084(11) 0.09296(12) 0.0346(3) Uani d . 1 1 . .
C C12 0.44804(17) 0.45625(12) 0.13303(12) 0.0369(3) Uani d . 1 1 . .
H H12 0.5318 0.4261 0.1825 0.044 Uiso calc R 1 1 . .
C C13 0.45728(18) 0.55621(12) 0.10004(12) 0.0386(3) Uani d . 1 1 . .
H H13 0.5469 0.5935 0.1267 0.046 Uiso calc R 1 1 . .
C C14 0.33194(18) 0.59989(11) 0.02710(12) 0.0371(3) Uani d . 1 1 . .
C C15 0.19922(18) 0.54565(13) -0.01497(13) 0.0432(4) Uani d . 1 1 . .
H H15 0.1160 0.5759 -0.0649 0.052 Uiso calc R 1 1 . .
C C16 0.19120(19) 0.44518(12) 0.01807(13) 0.0421(4) Uani d . 1 1 . .
H H16 0.1024 0.4075 -0.0102 0.051 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'
Cl Cl 0.1484 0.1585 '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'
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
C7 N1 C1 . . 127.41(13) ?
C7 N1 H1N . . 116.8(13) ?
C1 N1 H1N . . 115.7(13) ?
C10 N2 C11 . . 123.13(13) ?
C10 N2 H2N . . 116.6(13) ?
C11 N2 H2N . . 119.9(13) ?
C6 C1 C2 . . 118.92(14) ?
C6 C1 N1 . . 117.23(13) ?
C2 C1 N1 . . 123.84(14) ?
C3 C2 C1 . . 120.13(15) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C4 C3 C2 . . 120.08(16) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.71(15) ?
C3 C4 Cl1 . . 119.28(13) ?
C5 C4 Cl1 . . 120.00(13) ?
C4 C5 C6 . . 119.34(15) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 120.82(15) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
O1 C7 N1 . . 122.38(14) ?
O1 C7 C8 . . 123.75(14) ?
N1 C7 C8 . . 113.87(13) ?
C9 C8 C7 . . 129.78(14) ?
C9 C8 H8 . . 115.1 ?
C7 C8 H8 . . 115.1 ?
C8 C9 C10 . . 135.51(14) ?
C8 C9 H9 . . 112.2 ?
C10 C9 H9 . . 112.2 ?
O2 C10 N2 . . 123.26(14) ?
O2 C10 C9 . . 117.45(13) ?
N2 C10 C9 . . 119.29(13) ?
C12 C11 C16 . . 119.78(14) ?
C12 C11 N2 . . 119.54(14) ?
C16 C11 N2 . . 120.66(14) ?
C11 C12 C13 . . 120.37(14) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C14 C13 C12 . . 119.10(15) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
C15 C14 C13 . . 121.49(14) ?
C15 C14 Cl2 . . 119.37(12) ?
C13 C14 Cl2 . . 119.12(12) ?
C14 C15 C16 . . 119.04(15) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
C11 C16 C15 . . 120.21(15) ?
C11 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
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
Cl1 C4 . 1.7440(16) ?
Cl2 C14 . 1.7367(15) ?
O1 C7 . 1.2280(18) ?
O2 C10 . 1.2322(18) ?
N1 C7 . 1.3481(19) ?
N1 C1 . 1.4149(19) ?
N1 H1N . 0.843(14) ?
N2 C10 . 1.3369(19) ?
N2 C11 . 1.4255(19) ?
N2 H2N . 0.860(14) ?
C1 C6 . 1.387(2) ?
C1 C2 . 1.393(2) ?
C2 C3 . 1.380(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.374(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.377(2) ?
C5 C6 . 1.383(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.485(2) ?
C8 C9 . 1.332(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.496(2) ?
C9 H9 . 0.9300 ?
C11 C12 . 1.382(2) ?
C11 C16 . 1.384(2) ?
C12 C13 . 1.382(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.378(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.375(2) ?
C15 C16 . 1.387(2) ?
C15 H15 . 0.9300 ?
C16 H16 . 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
N1 H1N O2 2_545 0.843(14) 2.052(15) 2.8836(16) 168.9(17)
N2 H2N O1 . 0.860(14) 1.833(15) 2.6639(17) 161.7(18)
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
C7 N1 C1 C6 . . . . 174.16(15) ?
C7 N1 C1 C2 . . . . -7.0(3) ?
C6 C1 C2 C3 . . . . 0.1(3) ?
N1 C1 C2 C3 . . . . -178.74(16) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 0.0(3) ?
C2 C3 C4 Cl1 . . . . -178.68(14) ?
C3 C4 C5 C6 . . . . -0.6(2) ?
Cl1 C4 C5 C6 . . . . 178.10(12) ?
C4 C5 C6 C1 . . . . 0.9(2) ?
C2 C1 C6 C5 . . . . -0.7(2) ?
N1 C1 C6 C5 . . . . 178.25(14) ?
C1 N1 C7 O1 . . . . -2.6(3) ?
C1 N1 C7 C8 . . . . 177.38(14) ?
O1 C7 C8 C9 . . . . 3.0(3) ?
N1 C7 C8 C9 . . . . -176.98(17) ?
C7 C8 C9 C10 . . . . -0.8(3) ?
C11 N2 C10 O2 . . . . -0.6(3) ?
C11 N2 C10 C9 . . . . 178.80(14) ?
C8 C9 C10 O2 . . . . -173.19(19) ?
C8 C9 C10 N2 . . . . 7.4(3) ?
C10 N2 C11 C12 . . . . 122.66(17) ?
C10 N2 C11 C16 . . . . -59.1(2) ?
C16 C11 C12 C13 . . . . 1.0(2) ?
N2 C11 C12 C13 . . . . 179.29(13) ?
C11 C12 C13 C14 . . . . 0.3(2) ?
C12 C13 C14 C15 . . . . -1.3(2) ?
C12 C13 C14 Cl2 . . . . -179.70(11) ?
C13 C14 C15 C16 . . . . 0.9(2) ?
Cl2 C14 C15 C16 . . . . 179.31(12) ?
C12 C11 C16 C15 . . . . -1.4(2) ?
N2 C11 C16 C15 . . . . -179.66(14) ?
C14 C15 C16 C11 . . . . 0.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656680
