#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/38/2233863.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_2233863
loop_
_publ_author_name
'Foo, Chuan Ching'
'Tan, Ai Ling'
'Wimmer, Franz L.'
'Mirza, Aminul Huq'
'Young, David J.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 4,5-Diphenoxybenzene-1,2-dicarbonitrile
;
_journal_coeditor_code           HG5172
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o601
_journal_paper_doi               10.1107/S1600536812004060
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H12 N2 O2'
_chemical_formula_moiety         'C20 H12 N2 O2'
_chemical_formula_sum            'C20 H12 N2 O2'
_chemical_formula_weight         312.32
_chemical_name_systematic
;
4,5-Diphenoxybenzene-1,2-dicarbonitrile
;
_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                   5.6543(4)
_cell_length_b                   13.5163(9)
_cell_length_c                   19.9498(17)
_cell_measurement_reflns_used    1267
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5009
_cell_measurement_theta_min      2.5326
_cell_volume                     1524.7(2)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            4325
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_correction_T_min  0.9736
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0538
_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)+(0.0522P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                1498
_reflns_number_total             2029
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5172.cif
_cod_data_source_block           I
_cod_database_code               2233863
_cod_database_fobs_code          2233863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
O O1 0.7480(4) 0.46056(17) 0.21758(11) 0.0246(5) Uani d . 1 1
O O2 0.8019(4) 0.49051(16) 0.08401(11) 0.0237(6) Uani d . 1 1
N N1 1.6503(5) 0.2459(2) 0.05129(14) 0.0276(7) Uani d . 1 1
N N2 1.5732(5) 0.1975(2) 0.24912(15) 0.0302(7) Uani d . 1 1
C C1 0.9365(6) 0.4161(2) 0.18642(16) 0.0205(7) Uani d . 1 1
C C2 0.9635(6) 0.4325(2) 0.11812(16) 0.0191(7) Uani d . 1 1
C C3 1.1429(6) 0.3878(2) 0.08308(17) 0.0217(7) Uani d . 1 1
H H3 1.1582 0.3992 0.0363 0.026 Uiso calc R 1 1
C C4 1.3028(6) 0.3257(2) 0.11572(16) 0.0215(8) Uani d . 1 1
C C5 1.2763(6) 0.3093(2) 0.18456(16) 0.0197(7) Uani d . 1 1
C C6 1.0916(6) 0.3539(2) 0.21997(17) 0.0196(7) Uani d . 1 1
H H6 1.0724 0.3417 0.2665 0.024 Uiso calc R 1 1
C C7 1.4946(6) 0.2810(2) 0.07954(16) 0.0218(7) Uani d . 1 1
C C8 1.4418(6) 0.2465(2) 0.22039(16) 0.0220(7) Uani d . 1 1
C C9 0.7792(6) 0.4909(2) 0.28421(16) 0.0210(7) Uani d . 1 1
C C10 0.6053(6) 0.4644(3) 0.32990(17) 0.0262(8) Uani d . 1 1
H H10 0.4760 0.4240 0.3168 0.031 Uiso calc R 1 1
C C11 0.6253(6) 0.4987(3) 0.39549(17) 0.0272(8) Uani d . 1 1
H H11 0.5082 0.4813 0.4275 0.033 Uiso calc R 1 1
C C12 0.8137(6) 0.5579(2) 0.41466(18) 0.0288(8) Uani d . 1 1
H H12 0.8254 0.5810 0.4595 0.035 Uiso calc R 1 1
C C13 0.9840(6) 0.5829(2) 0.36819(17) 0.0271(8) Uani d . 1 1
H H13 1.1136 0.6233 0.3812 0.033 Uiso calc R 1 1
C C14 0.9673(6) 0.5493(2) 0.30229(17) 0.0248(8) Uani d . 1 1
H H14 1.0848 0.5665 0.2703 0.030 Uiso calc R 1 1
C C15 0.8279(5) 0.5936(2) 0.08943(16) 0.0200(7) Uani d . 1 1
C C16 1.0254(6) 0.6379(2) 0.11785(16) 0.0220(8) Uani d . 1 1
H H16 1.1490 0.5989 0.1363 0.026 Uiso calc R 1 1
C C17 1.0384(6) 0.7406(3) 0.11868(16) 0.0244(8) Uani d . 1 1
H H17 1.1726 0.7720 0.1378 0.029 Uiso calc R 1 1
C C18 0.8576(6) 0.7979(2) 0.09186(16) 0.0251(8) Uani d . 1 1
H H18 0.8667 0.8681 0.0932 0.030 Uiso calc R 1 1
C C19 0.6632(6) 0.7514(3) 0.06305(16) 0.0253(8) Uani d . 1 1
H H19 0.5397 0.7901 0.0441 0.030 Uiso calc R 1 1
C C20 0.6483(6) 0.6491(2) 0.06170(16) 0.0233(8) Uani d . 1 1
H H20 0.5156 0.6176 0.0419 0.028 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'
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
C1 O1 C9 117.4(2)
C2 O2 C15 117.1(2)
O1 C1 C6 122.5(3)
O1 C1 C2 117.4(3)
C6 C1 C2 120.1(3)
C3 C2 O2 119.2(3)
C3 C2 C1 120.7(3)
O2 C2 C1 120.1(3)
C2 C3 C4 120.4(3)
C2 C3 H3 119.8
C4 C3 H3 119.8
C3 C4 C5 119.0(3)
C3 C4 C7 120.5(3)
C5 C4 C7 120.5(3)
C6 C5 C4 120.5(3)
C6 C5 C8 119.0(3)
C4 C5 C8 120.5(3)
C1 C6 C5 119.3(3)
C1 C6 H6 120.3
C5 C6 H6 120.3
N1 C7 C4 178.9(3)
N2 C8 C5 179.4(4)
C14 C9 C10 121.7(3)
C14 C9 O1 121.0(3)
C10 C9 O1 117.2(3)
C9 C10 C11 118.3(3)
C9 C10 H10 120.9
C11 C10 H10 120.9
C12 C11 C10 120.9(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C13 C12 C11 119.5(3)
C13 C12 H12 120.2
C11 C12 H12 120.2
C12 C13 C14 120.4(3)
C12 C13 H13 119.8
C14 C13 H13 119.8
C9 C14 C13 119.2(3)
C9 C14 H14 120.4
C13 C14 H14 120.4
C20 C15 C16 121.4(3)
C20 C15 O2 115.6(3)
C16 C15 O2 122.9(3)
C15 C16 C17 118.6(3)
C15 C16 H16 120.7
C17 C16 H16 120.7
C18 C17 C16 120.9(3)
C18 C17 H17 119.6
C16 C17 H17 119.6
C17 C18 C19 119.2(3)
C17 C18 H18 120.4
C19 C18 H18 120.4
C20 C19 C18 120.5(3)
C20 C19 H19 119.8
C18 C19 H19 119.8
C15 C20 C19 119.4(3)
C15 C20 H20 120.3
C19 C20 H20 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.373(4)
O1 C9 1.402(4)
O2 C2 1.383(4)
O2 C15 1.405(3)
N1 C7 1.148(4)
N2 C8 1.148(4)
C1 C6 1.387(4)
C1 C2 1.389(4)
C2 C3 1.372(4)
C3 C4 1.395(4)
C3 H3 0.9500
C4 C5 1.399(4)
C4 C7 1.436(5)
C5 C6 1.398(5)
C5 C8 1.452(5)
C6 H6 0.9500
C9 C14 1.372(5)
C9 C10 1.388(5)
C10 C11 1.393(5)
C10 H10 0.9500
C11 C12 1.386(5)
C11 H11 0.9500
C12 C13 1.379(5)
C12 H12 0.9500
C13 C14 1.394(5)
C13 H13 0.9500
C14 H14 0.9500
C15 C20 1.379(4)
C15 C16 1.388(4)
C16 C17 1.390(4)
C16 H16 0.9500
C17 C18 1.390(5)
C17 H17 0.9500
C18 C19 1.391(5)
C18 H18 0.9500
C19 C20 1.385(4)
C19 H19 0.9500
C20 H20 0.9500
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
C13 H13 N1 4_855 0.95 2.52 3.422(4) 159
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
C9 O1 C1 C6 35.9(4)
C9 O1 C1 C2 -146.5(3)
C15 O2 C2 C3 -103.2(3)
C15 O2 C2 C1 80.0(4)
O1 C1 C2 C3 -177.7(3)
C6 C1 C2 C3 0.0(4)
O1 C1 C2 O2 -1.0(4)
C6 C1 C2 O2 176.7(3)
O2 C2 C3 C4 -177.4(3)
C1 C2 C3 C4 -0.7(5)
C2 C3 C4 C5 0.5(5)
C2 C3 C4 C7 -178.3(3)
C3 C4 C5 C6 0.4(5)
C7 C4 C5 C6 179.1(3)
C3 C4 C5 C8 -179.0(3)
C7 C4 C5 C8 -0.2(5)
O1 C1 C6 C5 178.4(3)
C2 C1 C6 C5 0.9(4)
C4 C5 C6 C1 -1.1(5)
C8 C5 C6 C1 178.3(3)
C3 C4 C7 N1 12E1(2)
C5 C4 C7 N1 -6E1(2)
C6 C5 C8 N2 -6E1(4)
C4 C5 C8 N2 12E1(4)
C1 O1 C9 C14 52.0(4)
C1 O1 C9 C10 -131.6(3)
C14 C9 C10 C11 0.1(5)
O1 C9 C10 C11 -176.3(3)
C9 C10 C11 C12 0.1(5)
C10 C11 C12 C13 -0.2(5)
C11 C12 C13 C14 0.1(5)
C10 C9 C14 C13 -0.1(5)
O1 C9 C14 C13 176.1(3)
C12 C13 C14 C9 0.0(5)
C2 O2 C15 C20 -172.5(3)
C2 O2 C15 C16 10.5(4)
C20 C15 C16 C17 0.8(5)
O2 C15 C16 C17 177.7(3)
C15 C16 C17 C18 0.2(5)
C16 C17 C18 C19 -0.9(5)
C17 C18 C19 C20 0.7(5)
C16 C15 C20 C19 -1.0(5)
O2 C15 C20 C19 -178.1(3)
C18 C19 C20 C15 0.2(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 592586
