#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/08/2230874.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_2230874
loop_
_publ_author_name
'Yang, Fei'
'Meng, Fanjun'
'Zhang, Xiaomei'
'Bai, Ming'
_publ_section_title
;
 Tetramethyl 5,5'-[4,5-dicyano-1,2-phenylenebis(oxy)]diisophthalate
 chloroform monosolvate
;
_journal_coeditor_code           SU2272
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1836
_journal_paper_doi               10.1107/S1600536811024718
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C28 H20 N2 O10, C H Cl3'
_chemical_formula_moiety         'C28 H20 N2 O10, C H Cl3'
_chemical_formula_sum            'C29 H21 Cl3 N2 O10'
_chemical_formula_weight         663.85
_chemical_name_systematic
;
Tetramethyl 5,5'-[4,5-dicyano-1,2-phenylenebis(oxy)]diisophthalate chloroform
monosolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.860(2)
_cell_angle_beta                 94.578(2)
_cell_angle_gamma                105.326(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9223(13)
_cell_length_b                   11.4374(15)
_cell_length_c                   13.9398(19)
_cell_measurement_reflns_used    1932
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.57
_cell_measurement_theta_min      2.74
_cell_volume                     1504.5(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0533
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7568
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.492
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0555
_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)+(0.0657P)²+0.6098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1587
_reflns_number_gt                3557
_reflns_number_total             5257
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su2272.cif
_cod_data_source_block           I
_cod_database_code               2230874
_cod_database_fobs_code          2230874
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.33835(13) 0.52563(10) 0.60702(9) 0.0890(4) Uani d . 1 1 . .
Cl Cl2 0.27318(15) 0.33393(13) 0.44608(10) 0.1086(5) Uani d . 1 1 . .
Cl Cl3 0.25891(16) 0.27612(12) 0.63996(12) 0.1147(5) Uani d . 1 1 . .
O O1 0.0551(2) 0.25073(18) 0.19677(15) 0.0442(5) Uani d . 1 1 . .
O O2 0.2198(2) 0.12734(18) 0.26465(14) 0.0449(5) Uani d . 1 1 . .
O O3 0.3694(3) -0.2971(3) 0.4139(3) 0.0968(11) Uani d . 1 1 . .
O O4 0.1564(2) -0.2758(2) 0.37967(19) 0.0617(6) Uani d . 1 1 . .
O O5 0.7479(3) 0.2270(2) 0.3509(2) 0.0726(7) Uani d . 1 1 . .
O O6 0.7752(2) 0.0552(2) 0.39934(19) 0.0641(7) Uani d . 1 1 . .
O O7 0.2002(2) 0.7618(2) 0.09592(19) 0.0631(7) Uani d . 1 1 . .
O O8 0.3489(2) 0.6556(2) 0.1366(2) 0.0668(7) Uani d . 1 1 . .
O O9 -0.3096(2) 0.5709(2) 0.0965(2) 0.0718(8) Uani d . 1 1 . .
O O10 -0.3797(2) 0.3866(2) 0.14128(19) 0.0609(7) Uani d . 1 1 . .
N N1 0.0918(4) 0.1109(3) -0.2174(2) 0.0726(9) Uani d . 1 1 . .
N N2 0.3628(4) -0.0670(3) -0.1112(2) 0.0697(9) Uani d . 1 1 . .
C C1 0.0951(4) -0.3963(3) 0.4050(3) 0.0742(11) Uani d . 1 1 . .
H H1A -0.0057 -0.4147 0.3956 0.111 Uiso calc R 1 1 . .
H H1B 0.1255 -0.3975 0.4719 0.111 Uiso calc R 1 1 . .
H H1C 0.1247 -0.4564 0.3643 0.111 Uiso calc R 1 1 . .
C C2 0.2951(4) -0.2372(3) 0.3889(2) 0.0520(8) Uani d . 1 1 . .
C C3 0.9268(4) 0.1075(4) 0.4124(3) 0.0765(12) Uani d . 1 1 . .
H H3A 0.9712 0.0493 0.4353 0.115 Uiso calc R 1 1 . .
H H3B 0.9512 0.1807 0.4591 0.115 Uiso calc R 1 1 . .
H H3C 0.9584 0.1269 0.3514 0.115 Uiso calc R 1 1 . .
C C4 0.6988(3) 0.1245(3) 0.3676(2) 0.0480(8) Uani d . 1 1 . .
C C5 0.5452(3) 0.0611(3) 0.3552(2) 0.0423(7) Uani d . 1 1 . .
C C6 0.4918(3) -0.0554(3) 0.3781(2) 0.0427(7) Uani d . 1 1 . .
H H6 0.5526 -0.0971 0.4026 0.051 Uiso calc R 1 1 . .
C C7 0.3471(3) -0.1105(3) 0.3645(2) 0.0406(7) Uani d . 1 1 . .
C C8 0.2562(3) -0.0503(3) 0.3263(2) 0.0414(7) Uani d . 1 1 . .
H H8 0.1597 -0.0868 0.3163 0.050 Uiso calc R 1 1 . .
C C9 0.3125(3) 0.0655(3) 0.3032(2) 0.0405(7) Uani d . 1 1 . .
C C10 0.4542(3) 0.1227(3) 0.3169(2) 0.0440(7) Uani d . 1 1 . .
H H10 0.4889 0.2009 0.3009 0.053 Uiso calc R 1 1 . .
C C11 0.1995(3) 0.1196(2) 0.1661(2) 0.0344(6) Uani d . 1 1 . .
C C12 0.2607(3) 0.0520(2) 0.1030(2) 0.0383(7) Uani d . 1 1 . .
H H12 0.3180 0.0072 0.1272 0.046 Uiso calc R 1 1 . .
C C13 0.2363(3) 0.0511(2) 0.0030(2) 0.0370(7) Uani d . 1 1 . .
C C14 0.1470(3) 0.1163(2) -0.0330(2) 0.0388(7) Uani d . 1 1 . .
C C15 0.0845(3) 0.1825(2) 0.0309(2) 0.0390(7) Uani d . 1 1 . .
H H15 0.0235 0.2243 0.0069 0.047 Uiso calc R 1 1 . .
C C16 0.1129(3) 0.1864(2) 0.1303(2) 0.0334(6) Uani d . 1 1 . .
C C17 0.3050(3) -0.0161(3) -0.0612(2) 0.0461(8) Uani d . 1 1 . .
C C18 0.1171(3) 0.1129(3) -0.1363(3) 0.0475(8) Uani d . 1 1 . .
C C19 -0.5227(3) 0.3945(4) 0.1327(4) 0.0805(13) Uani d . 1 1 . .
H H19A -0.5841 0.3203 0.1474 0.121 Uiso calc R 1 1 . .
H H19B -0.5497 0.4057 0.0675 0.121 Uiso calc R 1 1 . .
H H19C -0.5296 0.4627 0.1774 0.121 Uiso calc R 1 1 . .
C C20 -0.2831(3) 0.4828(3) 0.1232(2) 0.0460(8) Uani d . 1 1 . .
C C21 0.4657(4) 0.7573(3) 0.1234(3) 0.0764(12) Uani d . 1 1 . .
H H21A 0.5525 0.7368 0.1364 0.115 Uiso calc R 1 1 . .
H H21B 0.4659 0.8286 0.1674 0.115 Uiso calc R 1 1 . .
H H21C 0.4560 0.7738 0.0576 0.115 Uiso calc R 1 1 . .
C C22 0.2215(3) 0.6710(3) 0.1206(2) 0.0444(7) Uani d . 1 1 . .
C C23 0.1085(3) 0.5622(3) 0.1353(2) 0.0383(7) Uani d . 1 1 . .
C C24 0.1361(3) 0.4546(3) 0.1580(2) 0.0423(7) Uani d . 1 1 . .
H H24 0.2280 0.4489 0.1648 0.051 Uiso calc R 1 1 . .
C C25 0.0262(3) 0.3570(2) 0.1704(2) 0.0369(7) Uani d . 1 1 . .
C C26 -0.1108(3) 0.3622(2) 0.1620(2) 0.0378(7) Uani d . 1 1 . .
H H26 -0.1836 0.2959 0.1717 0.045 Uiso calc R 1 1 . .
C C27 -0.1380(3) 0.4696(2) 0.1384(2) 0.0368(6) Uani d . 1 1 . .
C C28 -0.0290(3) 0.5684(2) 0.1264(2) 0.0388(7) Uani d . 1 1 . .
H H28 -0.0484 0.6401 0.1121 0.047 Uiso calc R 1 1 . .
C C29 0.3476(4) 0.3780(3) 0.5670(3) 0.0693(10) Uani d . 1 1 . .
H H29 0.4465 0.3775 0.5714 0.083 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'
O O 0.0106 0.0060 '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'
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 O1 C25 . . 116.6(2) ?
C11 O2 C9 . . 117.2(2) ?
C2 O4 C1 . . 116.7(3) ?
C4 O6 C3 . . 116.7(3) ?
C22 O8 C21 . . 116.1(3) ?
C20 O10 C19 . . 116.2(3) ?
O4 C1 H1A . . 109.5 ?
O4 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O4 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O3 C2 O4 . . 123.5(3) ?
O3 C2 C7 . . 124.3(3) ?
O4 C2 C7 . . 112.3(3) ?
O6 C3 H3A . . 109.5 ?
O6 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
O6 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
O5 C4 O6 . . 123.8(3) ?
O5 C4 C5 . . 124.0(3) ?
O6 C4 C5 . . 112.2(3) ?
C6 C5 C10 . . 119.9(3) ?
C6 C5 C4 . . 122.6(3) ?
C10 C5 C4 . . 117.4(3) ?
C5 C6 C7 . . 120.1(3) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C6 . . 120.3(3) ?
C8 C7 C2 . . 121.6(3) ?
C6 C7 C2 . . 118.0(3) ?
C9 C8 C7 . . 118.3(3) ?
C9 C8 H8 . . 120.8 ?
C7 C8 H8 . . 120.8 ?
C10 C9 C8 . . 122.7(3) ?
C10 C9 O2 . . 118.9(3) ?
C8 C9 O2 . . 118.4(3) ?
C9 C10 C5 . . 118.6(3) ?
C9 C10 H10 . . 120.7 ?
C5 C10 H10 . . 120.7 ?
O2 C11 C12 . . 123.7(2) ?
O2 C11 C16 . . 116.0(2) ?
C12 C11 C16 . . 120.3(3) ?
C11 C12 C13 . . 119.9(2) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C12 C13 C14 . . 119.7(3) ?
C12 C13 C17 . . 119.1(3) ?
C14 C13 C17 . . 121.2(3) ?
C15 C14 C13 . . 120.0(3) ?
C15 C14 C18 . . 119.7(3) ?
C13 C14 C18 . . 120.3(3) ?
C16 C15 C14 . . 120.0(3) ?
C16 C15 H15 . . 120.0 ?
C14 C15 H15 . . 120.0 ?
O1 C16 C15 . . 122.6(2) ?
O1 C16 C11 . . 117.3(2) ?
C15 C16 C11 . . 120.0(3) ?
N2 C17 C13 . . 178.1(4) ?
N1 C18 C14 . . 178.9(4) ?
O10 C19 H19A . . 109.5 ?
O10 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O10 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O9 C20 O10 . . 123.5(3) ?
O9 C20 C27 . . 123.7(3) ?
O10 C20 C27 . . 112.8(2) ?
O8 C21 H21A . . 109.5 ?
O8 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O8 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O7 C22 O8 . . 123.6(3) ?
O7 C22 C23 . . 123.9(3) ?
O8 C22 C23 . . 112.4(2) ?
C28 C23 C24 . . 119.0(3) ?
C28 C23 C22 . . 118.5(2) ?
C24 C23 C22 . . 122.6(3) ?
C25 C24 C23 . . 119.5(3) ?
C25 C24 H24 . . 120.2 ?
C23 C24 H24 . . 120.2 ?
C26 C25 C24 . . 122.1(2) ?
C26 C25 O1 . . 118.6(2) ?
C24 C25 O1 . . 119.2(2) ?
C25 C26 C27 . . 118.2(3) ?
C25 C26 H26 . . 120.9 ?
C27 C26 H26 . . 120.9 ?
C28 C27 C26 . . 120.5(3) ?
C28 C27 C20 . . 117.0(2) ?
C26 C27 C20 . . 122.5(3) ?
C27 C28 C23 . . 120.8(2) ?
C27 C28 H28 . . 119.6 ?
C23 C28 H28 . . 119.6 ?
Cl1 C29 Cl2 . . 109.5(2) ?
Cl1 C29 Cl3 . . 109.9(2) ?
Cl2 C29 Cl3 . . 110.2(2) ?
Cl1 C29 H29 . . 109.1 ?
Cl2 C29 H29 . . 109.1 ?
Cl3 C29 H29 . . 109.1 ?
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 C29 . 1.743(4) ?
Cl2 C29 . 1.744(4) ?
Cl3 C29 . 1.747(4) ?
O1 C16 . 1.369(3) ?
O1 C25 . 1.403(3) ?
O2 C11 . 1.362(3) ?
O2 C9 . 1.411(3) ?
O3 C2 . 1.191(4) ?
O4 C2 . 1.320(4) ?
O4 C1 . 1.449(4) ?
O5 C4 . 1.203(4) ?
O6 C4 . 1.322(4) ?
O6 C3 . 1.452(4) ?
O7 C22 . 1.196(4) ?
O8 C22 . 1.327(4) ?
O8 C21 . 1.450(4) ?
O9 C20 . 1.199(4) ?
O10 C20 . 1.320(4) ?
O10 C19 . 1.442(4) ?
N1 C18 . 1.135(4) ?
N2 C17 . 1.139(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.493(4) ?
C3 H3A . 0.9600 ?
C3 H3B . 0.9600 ?
C3 H3C . 0.9600 ?
C4 C5 . 1.492(4) ?
C5 C6 . 1.383(4) ?
C5 C10 . 1.395(4) ?
C6 C7 . 1.395(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.383(4) ?
C8 C9 . 1.381(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.372(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.383(4) ?
C11 C16 . 1.392(4) ?
C12 C13 . 1.394(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.400(4) ?
C13 C17 . 1.438(4) ?
C14 C15 . 1.389(4) ?
C14 C18 . 1.440(4) ?
C15 C16 . 1.385(4) ?
C15 H15 . 0.9300 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 C27 . 1.488(4) ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 C23 . 1.486(4) ?
C23 C28 . 1.382(4) ?
C23 C24 . 1.395(4) ?
C24 C25 . 1.377(4) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.373(4) ?
C26 C27 . 1.396(4) ?
C26 H26 . 0.9300 ?
C27 C28 . 1.379(4) ?
C28 H28 . 0.9300 ?
C29 H29 . 0.9800 ?
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
C15 H15 O7 2_565 0.93 2.60 3.455(4) 154 yes
C29 H29 O3 2_656 0.98 2.26 3.182(5) 157 yes
C19 H19A Cg2 1_455 0.98 2.90 3.709(4) 143 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656801
