#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227957.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_2227957
loop_
_publ_author_name
'Yu, Lijuan'
'Zhou, Xiaole'
'Yin, Yinghui'
'Li, Renjie'
'Peng, Tianyou'
_publ_section_title
;
 4,5-Bis(4-methoxyphenoxy)phthalonitrile
;
_journal_coeditor_code           RZ2481
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2527
_journal_paper_doi               10.1107/S1600536810035610
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C22 H16 N2 O4'
_chemical_formula_sum            'C22 H16 N2 O4'
_chemical_formula_weight         372.37
_chemical_name_common
;
4,5-bis(4-methoxyphenoxy)phthalonitrile
;
_chemical_name_systematic
;
4,5-bis(4-methoxyphenoxy)benzene-1,2-dicarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.5510(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7614(2)
_cell_length_b                   10.49260(10)
_cell_length_c                   14.0701(2)
_cell_measurement_reflns_used    5549
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.48
_cell_measurement_theta_min      2.50
_cell_volume                     1876.28(4)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scan'
_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  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24018
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9881
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0379
_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)+(0.0369P)²+0.4099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                2189
_reflns_number_total             3311
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2481.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227957
_cod_database_fobs_code          2227957
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
C C17 0.07245(13) 0.02765(18) 0.29042(13) 0.0566(5) Uani d . 1 . .
H H17 0.0524 0.1096 0.2653 0.068 Uiso calc R 1 . .
N N2 0.54537(15) 0.17422(18) 0.53262(13) 0.0822(6) Uani d . 1 . .
N N1 0.63571(15) 0.30662(18) 0.31740(13) 0.0820(5) Uani d . 1 . .
C C2 0.49439(14) 0.16026(18) 0.44763(15) 0.0572(5) Uani d . 1 . .
C C1 0.55634(16) 0.25589(18) 0.29120(14) 0.0598(5) Uani d . 1 . .
O O1 0.22453(9) 0.09523(14) 0.03832(9) 0.0684(4) Uani d . 1 . .
O O2 0.16999(9) 0.01007(12) 0.18264(8) 0.0621(4) Uani d . 1 . .
O O3 0.33469(11) 0.01535(14) -0.29526(10) 0.0796(4) Uani d . 1 . .
O O4 0.02251(11) -0.19057(15) 0.46372(11) 0.0843(5) Uani d . 1 . .
C C5 0.33212(13) 0.08186(16) 0.31600(12) 0.0496(4) Uani d . 1 . .
H H5 0.3124 0.0507 0.3679 0.060 Uiso calc R 1 . .
C C3 0.45763(13) 0.19033(16) 0.26340(13) 0.0494(4) Uani d . 1 . .
C C7 0.29686(13) 0.11161(17) 0.13679(12) 0.0510(4) Uani d . 1 . .
C C6 0.26639(13) 0.06676(16) 0.21448(12) 0.0485(4) Uani d . 1 . .
C C4 0.42795(13) 0.14356(16) 0.34096(12) 0.0475(4) Uani d . 1 . .
C C8 0.39146(13) 0.17408(16) 0.16126(13) 0.0534(5) Uani d . 1 . .
H H8 0.4109 0.2053 0.1092 0.064 Uiso calc R 1 . .
C C9 0.25752(13) 0.07923(17) -0.04349(12) 0.0513(4) Uani d . 1 . .
C C11 0.21973(15) 0.11325(19) -0.22164(13) 0.0611(5) Uani d . 1 . .
H H11 0.1780 0.1501 -0.2841 0.073 Uiso calc R 1 . .
C C12 0.30366(15) 0.03855(18) -0.21509(13) 0.0561(5) Uani d . 1 . .
C C10 0.19704(14) 0.13386(19) -0.13506(13) 0.0599(5) Uani d . 1 . .
H H10 0.1404 0.1851 -0.1394 0.072 Uiso calc R 1 . .
C C14 0.34035(16) 0.0024(2) -0.03671(14) 0.0701(6) Uani d . 1 . .
H H14 0.3807 -0.0364 0.0253 0.084 Uiso calc R 1 . .
C C15 0.25790(19) 0.0227(2) -0.39650(15) 0.0916(7) Uani d . 1 . .
H H15A 0.1982 -0.0284 -0.4017 0.137 Uiso calc R 1 . .
H H15B 0.2871 -0.0083 -0.4441 0.137 Uiso calc R 1 . .
H H15C 0.2362 0.1097 -0.4125 0.137 Uiso calc R 1 . .
C C13 0.36321(16) -0.0166(2) -0.12246(15) 0.0729(6) Uani d . 1 . .
H H13 0.4200 -0.0679 -0.1177 0.087 Uiso calc R 1 . .
C C16 0.13818(13) -0.04202(18) 0.25815(12) 0.0500(4) Uani d . 1 . .
C C19 0.06522(13) -0.14685(19) 0.39663(13) 0.0562(5) Uani d . 1 . .
C C18 0.03643(14) -0.02478(19) 0.36030(14) 0.0611(5) Uani d . 1 . .
H H18 -0.0076 0.0223 0.3832 0.073 Uiso calc R 1 . .
C C20 0.13229(14) -0.21514(19) 0.36496(14) 0.0605(5) Uani d . 1 . .
H H20 0.1529 -0.2968 0.3903 0.073 Uiso calc R 1 . .
C C21 0.16913(14) -0.16199(19) 0.29513(14) 0.0610(5) Uani d . 1 . .
H H21 0.2148 -0.2077 0.2735 0.073 Uiso calc R 1 . .
C C22 0.05311(19) -0.3141(2) 0.50731(17) 0.0959(8) Uani d . 1 . .
H H22A 0.0348 -0.3764 0.4533 0.144 Uiso calc R 1 . .
H H22B 0.0174 -0.3333 0.5523 0.144 Uiso calc R 1 . .
H H22C 0.1278 -0.3156 0.5457 0.144 Uiso calc R 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 C17 C18 . . 119.27(18) ?
C16 C17 H17 . . 120.4 ?
C18 C17 H17 . . 120.4 ?
N2 C2 C4 . . 178.6(2) ?
N1 C1 C3 . . 177.2(2) ?
C7 O1 C9 . . 120.46(13) ?
C6 O2 C16 . . 117.85(12) ?
C12 O3 C15 . . 118.08(16) ?
C19 O4 C22 . . 117.84(16) ?
C6 C5 C4 . . 119.94(15) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C8 C3 C4 . . 119.71(16) ?
C8 C3 C1 . . 121.20(16) ?
C4 C3 C1 . . 119.08(15) ?
O1 C7 C8 . . 124.19(15) ?
O1 C7 C6 . . 115.44(15) ?
C8 C7 C6 . . 120.27(15) ?
O2 C6 C5 . . 124.12(15) ?
O2 C6 C7 . . 115.91(14) ?
C5 C6 C7 . . 119.96(16) ?
C5 C4 C3 . . 120.11(15) ?
C5 C4 C2 . . 118.90(15) ?
C3 C4 C2 . . 120.98(15) ?
C7 C8 C3 . . 119.99(16) ?
C7 C8 H8 . . 120.0 ?
C3 C8 H8 . . 120.0 ?
C10 C9 C14 . . 120.23(17) ?
C10 C9 O1 . . 116.98(16) ?
C14 C9 O1 . . 122.49(16) ?
C12 C11 C10 . . 119.92(17) ?
C12 C11 H11 . . 120.0 ?
C10 C11 H11 . . 120.0 ?
C11 C12 O3 . . 124.51(17) ?
C11 C12 C13 . . 119.09(18) ?
O3 C12 C13 . . 116.40(18) ?
C9 C10 C11 . . 120.23(18) ?
C9 C10 H10 . . 119.9 ?
C11 C10 H10 . . 119.9 ?
C9 C14 C13 . . 119.32(17) ?
C9 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
O3 C15 H15A . . 109.5 ?
O3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C14 C13 C12 . . 121.19(19) ?
C14 C13 H13 . . 119.4 ?
C12 C13 H13 . . 119.4 ?
C21 C16 C17 . . 120.99(16) ?
C21 C16 O2 . . 120.27(16) ?
C17 C16 O2 . . 118.68(17) ?
O4 C19 C20 . . 124.73(18) ?
O4 C19 C18 . . 115.37(17) ?
C20 C19 C18 . . 119.89(17) ?
C17 C18 C19 . . 120.37(17) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C19 C20 C21 . . 119.71(18) ?
C19 C20 H20 . . 120.1 ?
C21 C20 H20 . . 120.1 ?
C16 C21 C20 . . 119.74(17) ?
C16 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
O4 C22 H22A . . 109.5 ?
O4 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O4 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
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
C17 C16 . 1.369(2) ?
C17 C18 . 1.374(2) ?
C17 H17 . 0.9300 ?
N2 C2 . 1.140(2) ?
N1 C1 . 1.142(2) ?
C2 C4 . 1.438(2) ?
C1 C3 . 1.437(3) ?
O1 C7 . 1.3719(19) ?
O1 C9 . 1.400(2) ?
O2 C6 . 1.3633(19) ?
O2 C16 . 1.4057(19) ?
O3 C12 . 1.372(2) ?
O3 C15 . 1.413(2) ?
O4 C19 . 1.369(2) ?
O4 C22 . 1.426(3) ?
C5 C6 . 1.376(2) ?
C5 C4 . 1.388(2) ?
C5 H5 . 0.9300 ?
C3 C8 . 1.386(2) ?
C3 C4 . 1.393(2) ?
C7 C8 . 1.378(2) ?
C7 C6 . 1.394(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.363(2) ?
C9 C14 . 1.369(2) ?
C11 C12 . 1.369(3) ?
C11 C10 . 1.386(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.373(3) ?
C10 H10 . 0.9300 ?
C14 C13 . 1.373(3) ?
C14 H14 . 0.9300 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C13 H13 . 0.9300 ?
C16 C21 . 1.366(2) ?
C19 C20 . 1.371(2) ?
C19 C18 . 1.380(3) ?
C18 H18 . 0.9300 ?
C20 C21 . 1.384(2) ?
C20 H20 . 0.9300 ?
C21 H21 . 0.9300 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
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
C9 O1 C7 C8 . . . . 33.4(3) ?
C9 O1 C7 C6 . . . . -150.32(16) ?
C16 O2 C6 C5 . . . . -3.4(2) ?
C16 O2 C6 C7 . . . . 177.01(15) ?
C4 C5 C6 O2 . . . . -178.51(15) ?
C4 C5 C6 C7 . . . . 1.0(3) ?
O1 C7 C6 O2 . . . . 1.4(2) ?
C8 C7 C6 O2 . . . . 177.87(15) ?
O1 C7 C6 C5 . . . . -178.18(15) ?
C8 C7 C6 C5 . . . . -1.7(3) ?
C6 C5 C4 C3 . . . . 0.1(2) ?
C6 C5 C4 C2 . . . . 178.85(16) ?
C8 C3 C4 C5 . . . . -0.5(2) ?
C1 C3 C4 C5 . . . . 178.88(16) ?
C8 C3 C4 C2 . . . . -179.28(16) ?
C1 C3 C4 C2 . . . . 0.1(2) ?
O1 C7 C8 C3 . . . . 177.40(16) ?
C6 C7 C8 C3 . . . . 1.3(3) ?
C4 C3 C8 C7 . . . . -0.2(3) ?
C1 C3 C8 C7 . . . . -179.53(16) ?
C7 O1 C9 C10 . . . . -143.22(17) ?
C7 O1 C9 C14 . . . . 43.1(2) ?
C10 C11 C12 O3 . . . . -177.94(17) ?
C10 C11 C12 C13 . . . . 1.1(3) ?
C15 O3 C12 C11 . . . . -26.5(3) ?
C15 O3 C12 C13 . . . . 154.53(19) ?
C14 C9 C10 C11 . . . . -0.7(3) ?
O1 C9 C10 C11 . . . . -174.62(16) ?
C12 C11 C10 C9 . . . . -0.5(3) ?
C10 C9 C14 C13 . . . . 1.4(3) ?
O1 C9 C14 C13 . . . . 174.93(18) ?
C9 C14 C13 C12 . . . . -0.9(3) ?
C11 C12 C13 C14 . . . . -0.4(3) ?
O3 C12 C13 C14 . . . . 178.69(18) ?
C18 C17 C16 C21 . . . . -0.7(3) ?
C18 C17 C16 O2 . . . . 176.69(15) ?
C6 O2 C16 C21 . . . . -83.9(2) ?
C6 O2 C16 C17 . . . . 98.69(18) ?
C22 O4 C19 C20 . . . . 2.7(3) ?
C22 O4 C19 C18 . . . . -177.31(17) ?
C16 C17 C18 C19 . . . . -0.7(3) ?
O4 C19 C18 C17 . . . . -178.31(16) ?
C20 C19 C18 C17 . . . . 1.7(3) ?
O4 C19 C20 C21 . . . . 178.76(17) ?
C18 C19 C20 C21 . . . . -1.2(3) ?
C17 C16 C21 C20 . . . . 1.1(3) ?
O2 C16 C21 C20 . . . . -176.20(15) ?
C19 C20 C21 C16 . . . . -0.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2011242
