#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016997.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_2016997
loop_
_publ_author_name
'Hori, Kayako'
'Kouno, Naomi'
_publ_section_title
;
 Two crystal forms of mesogenic bis(4'-cyanobiphenyl-4-yl) butanedioate
;
_journal_coeditor_code           EG3008
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o108
_journal_page_last               o110
_journal_paper_doi               10.1107/S0108270109004041
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C30 H20 N2 O4'
_chemical_formula_moiety         'C30 H20 N2 O4'
_chemical_formula_sum            'C30 H20 N2 O4'
_chemical_formula_weight         472.48
_chemical_melting_point          498
_chemical_name_systematic
;
bis(4'-cyanobiphenyl-4-yl) butanedioate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.06(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.478(3)
_cell_length_b                   11.6064(11)
_cell_length_c                   9.590(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      22.5
_cell_volume                     1136.1(5)
_computing_cell_refinement       'PROCESS (Rigaku, 1996)'
_computing_data_collection       'PROCESS (Rigaku, 1996)'
_computing_data_reduction        'PROCESS (Rigaku, 1996)'
_computing_molecular_graphics
;
TEXSAN (Molecular Structure Corporation & Rigaku, 1996)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku AFC-7R'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2587
_diffrn_reflns_theta_full        68.01
_diffrn_reflns_theta_max         68.01
_diffrn_reflns_theta_min         4.33
_diffrn_standards_decay_%        0.26
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'oval plate'
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.237
_refine_ls_extinction_coef       0.0144(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0676P)²+0.4554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                1955
_reflns_number_total             2033
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3008.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016997
_cod_database_fobs_code          2016997
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
O O1 0.34484(10) 0.04546(11) 0.22003(12) 0.0347(3) Uani d . 1 . .
O O2 0.26457(10) 0.05620(11) -0.01839(12) 0.0361(3) Uani d . 1 . .
N N1 -0.53275(16) 0.20929(14) 0.64755(19) 0.0483(4) Uani d . 1 . .
C C1 -0.44609(16) 0.19595(14) 0.59542(18) 0.0351(4) Uani d . 1 . .
C C2 -0.33566(15) 0.17836(14) 0.53109(16) 0.0293(4) Uani d . 1 . .
C C3 -0.33186(16) 0.08356(15) 0.44384(17) 0.0337(4) Uani d . 1 . .
H H3 -0.4034 0.0313 0.4235 0.040 Uiso calc R 1 . .
C C4 -0.22379(15) 0.06533(14) 0.38655(17) 0.0324(4) Uani d . 1 . .
H H4 -0.2226 0.0006 0.3263 0.039 Uiso calc R 1 . .
C C5 -0.11603(13) 0.14006(13) 0.41517(15) 0.0254(4) Uani d . 1 . .
C C6 -0.12218(15) 0.23470(13) 0.50348(17) 0.0309(4) Uani d . 1 . .
H H6 -0.0504 0.2867 0.5249 0.037 Uiso calc R 1 . .
C C7 -0.23007(16) 0.25447(14) 0.56032(17) 0.0328(4) Uani d . 1 . .
H H7 -0.2323 0.3199 0.6193 0.039 Uiso calc R 1 . .
C C8 0.00057(14) 0.11911(13) 0.35395(15) 0.0259(4) Uani d . 1 . .
C C9 0.01032(15) 0.02110(15) 0.27398(18) 0.0339(4) Uani d . 1 . .
H H9 -0.0608 -0.0316 0.2540 0.041 Uiso calc R 1 . .
C C10 0.12098(16) -0.00184(15) 0.22256(18) 0.0365(4) Uani d . 1 . .
H H10 0.1257 -0.0694 0.1680 0.044 Uiso calc R 1 . .
C C11 0.22395(14) 0.07437(14) 0.25150(16) 0.0298(4) Uani d . 1 . .
C C12 0.21658(16) 0.17443(15) 0.32509(19) 0.0384(4) Uani d . 1 . .
H H12 0.2868 0.2281 0.3407 0.046 Uiso calc R 1 . .
C C13 0.10565(16) 0.19643(15) 0.3765(2) 0.0377(4) Uani d . 1 . .
H H13 0.1008 0.2655 0.4282 0.045 Uiso calc R 1 . .
C C14 0.35332(14) 0.03680(13) 0.08143(16) 0.0276(4) Uani d . 1 . .
C C15 0.48881(14) -0.00147(14) 0.07518(16) 0.0308(4) Uani d . 1 . .
H H15A 0.5031 -0.0809 0.1130 0.037 Uiso calc R 1 . .
H H15B 0.5537 0.0492 0.1373 0.037 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C14 O1 C11 . . 119.30(11) no
N1 C1 C2 . . 179.29(19) no
C3 C2 C7 . . 119.60(14) no
C3 C2 C1 . . 120.31(15) no
C7 C2 C1 . . 120.05(15) no
C4 C3 C2 . . 119.91(14) no
C4 C3 H3 . . 120.0 no
C2 C3 H3 . . 120.0 no
C3 C4 C5 . . 121.58(14) no
C3 C4 H4 . . 119.2 no
C5 C4 H4 . . 119.2 no
C6 C5 C4 . . 117.39(14) no
C6 C5 C8 . . 121.41(13) no
C4 C5 C8 . . 121.20(14) no
C7 C6 C5 . . 121.59(14) no
C7 C6 H6 . . 119.2 no
C5 C6 H6 . . 119.2 no
C6 C7 C2 . . 119.91(14) no
C6 C7 H7 . . 120.0 no
C2 C7 H7 . . 120.0 no
C9 C8 C13 . . 117.23(14) no
C9 C8 C5 . . 121.36(14) no
C13 C8 C5 . . 121.40(14) no
C10 C9 C8 . . 121.75(15) no
C10 C9 H9 . . 119.1 no
C8 C9 H9 . . 119.1 no
C11 C10 C9 . . 119.13(15) no
C11 C10 H10 . . 120.4 no
C9 C10 H10 . . 120.4 no
C12 C11 C10 . . 121.10(14) no
C12 C11 O1 . . 118.08(14) no
C10 C11 O1 . . 120.46(14) no
C11 C12 C13 . . 119.29(15) no
C11 C12 H12 . . 120.4 no
C13 C12 H12 . . 120.4 no
C12 C13 C8 . . 121.40(15) no
C12 C13 H13 . . 119.3 no
C8 C13 H13 . . 119.3 no
O2 C14 O1 . . 124.03(14) no
O2 C14 C15 . . 126.51(14) no
O1 C14 C15 . . 109.45(12) no
C14 C15 C15 . 3_655 112.52(15) no
C14 C15 H15A . . 109.1 no
C15 C15 H15A 3_655 . 109.1 no
C14 C15 H15B . . 109.1 no
C15 C15 H15B 3_655 . 109.1 no
H15A C15 H15B . . 107.8 no
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
O1 C14 . 1.3557(19) no
O1 C11 . 1.4074(18) no
O2 C14 . 1.1956(19) no
N1 C1 . 1.142(2) no
C1 C2 . 1.443(2) no
C2 C3 . 1.388(2) no
C2 C7 . 1.394(2) no
C3 C4 . 1.382(2) no
C3 H3 . 0.9500 no
C4 C5 . 1.401(2) no
C4 H4 . 0.9500 no
C5 C6 . 1.397(2) no
C5 C8 . 1.490(2) no
C6 C7 . 1.381(2) no
C6 H6 . 0.9500 no
C7 H7 . 0.9500 no
C8 C9 . 1.389(2) no
C8 C13 . 1.399(2) no
C9 C10 . 1.385(2) no
C9 H9 . 0.9500 no
C10 C11 . 1.374(2) no
C10 H10 . 0.9500 no
C11 C12 . 1.370(2) no
C12 C13 . 1.385(2) no
C12 H12 . 0.9500 no
C13 H13 . 0.9500 no
C14 C15 . 1.502(2) no
C15 C15 3_655 1.513(3) no
C15 H15A . 0.9900 no
C15 H15B . 0.9900 no
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 C2 C3 C4 . . . . -0.1(2) no
C1 C2 C3 C4 . . . . -177.85(15) no
C2 C3 C4 C5 . . . . 0.5(3) no
C3 C4 C5 C6 . . . . -0.4(2) no
C3 C4 C5 C8 . . . . 179.45(14) no
C4 C5 C6 C7 . . . . -0.2(2) no
C8 C5 C6 C7 . . . . 179.95(14) no
C5 C6 C7 C2 . . . . 0.7(2) no
C3 C2 C7 C6 . . . . -0.5(2) no
C1 C2 C7 C6 . . . . 177.27(15) no
C6 C5 C8 C9 . . . . 175.72(15) no
C4 C5 C8 C9 . . . . -4.2(2) no
C6 C5 C8 C13 . . . . -3.3(2) no
C4 C5 C8 C13 . . . . 176.86(15) no
C13 C8 C9 C10 . . . . 2.2(2) no
C5 C8 C9 C10 . . . . -176.81(14) no
C8 C9 C10 C11 . . . . 0.0(3) no
C9 C10 C11 C12 . . . . -2.7(3) no
C9 C10 C11 O1 . . . . 170.29(14) no
C14 O1 C11 C12 . . . . -118.01(16) no
C14 O1 C11 C10 . . . . 68.8(2) no
C10 C11 C12 C13 . . . . 2.9(3) no
O1 C11 C12 C13 . . . . -170.23(15) no
C11 C12 C13 C8 . . . . -0.5(3) no
C9 C8 C13 C12 . . . . -2.0(3) no
C5 C8 C13 C12 . . . . 177.05(15) no
C11 O1 C14 O2 . . . . 2.7(2) no
C11 O1 C14 C15 . . . . -176.67(13) no
O2 C14 C15 C15 . . . 3_655 7.9(3) no
O1 C14 C15 C15 . . . 3_655 -172.69(16) no
