#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/69/2016998.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_2016998
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_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                 97.452(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.9235(11)
_cell_length_b                   8.7879(10)
_cell_length_c                   13.4152(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      22.5
_cell_volume                     1160.0(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2846
_diffrn_reflns_theta_full        67.95
_diffrn_reflns_theta_max         67.95
_diffrn_reflns_theta_min         4.49
_diffrn_standards_decay_%        -3.05
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.209
_refine_ls_extinction_coef       0.0037(5)
_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   1.040
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0371
_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)+(0.0512P)²+0.3663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1046
_reflns_number_gt                1928
_reflns_number_total             2097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3008.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2016998
_cod_database_fobs_code          2016998
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 0.53710(10) -0.08728(11) 0.71712(7) 0.0361(3) Uani d . 1 . .
O O2 0.61269(10) 0.13196(11) 0.65649(7) 0.0382(3) Uani d . 1 . .
N N1 1.14390(14) -0.0570(2) 1.46662(10) 0.0559(4) Uani d . 1 . .
C C1 1.08008(14) -0.04991(18) 1.38933(11) 0.0391(3) Uani d . 1 . .
C C2 1.00031(13) -0.04484(15) 1.29165(9) 0.0308(3) Uani d . 1 . .
C C3 0.87076(14) 0.02009(16) 1.27896(9) 0.0322(3) Uani d . 1 . .
H H3 0.8352 0.0645 1.3346 0.039 Uiso calc R 1 . .
C C4 0.79441(13) 0.01957(15) 1.18505(9) 0.0302(3) Uani d . 1 . .
H H4 0.7071 0.0657 1.1764 0.036 Uiso calc R 1 . .
C C5 0.84404(13) -0.04808(14) 1.10257(9) 0.0286(3) Uani d . 1 . .
C C6 0.97534(14) -0.10996(16) 1.11679(10) 0.0338(3) Uani d . 1 . .
H H6 1.0115 -0.1543 1.0613 0.041 Uiso calc R 1 . .
C C7 1.05294(13) -0.10768(16) 1.20969(10) 0.0338(3) Uani d . 1 . .
H H7 1.1422 -0.1489 1.2178 0.041 Uiso calc R 1 . .
C C8 0.76131(13) -0.05489(14) 1.00228(9) 0.0291(3) Uani d . 1 . .
C C9 0.67238(14) 0.06198(15) 0.96762(9) 0.0317(3) Uani d . 1 . .
H H9 0.6626 0.1471 1.0097 0.038 Uiso calc R 1 . .
C C10 0.59778(14) 0.05626(15) 0.87251(10) 0.0332(3) Uani d . 1 . .
H H10 0.5378 0.1368 0.8494 0.040 Uiso calc R 1 . .
C C11 0.61228(14) -0.06819(15) 0.81233(9) 0.0307(3) Uani d . 1 . .
C C12 0.69804(16) -0.18617(16) 0.84508(10) 0.0381(3) Uani d . 1 . .
H H12 0.7063 -0.2716 0.8029 0.046 Uiso calc R 1 . .
C C13 0.77203(15) -0.17980(16) 0.93971(10) 0.0370(3) Uani d . 1 . .
H H13 0.8309 -0.2615 0.9624 0.044 Uiso calc R 1 . .
C C14 0.55481(12) 0.01303(15) 0.64236(9) 0.0276(3) Uani d . 1 . .
C C15 0.49264(14) -0.05225(15) 0.54361(9) 0.0322(3) Uani d . 1 . .
H H15A 0.3949 -0.0719 0.5463 0.039 Uiso calc R 1 . .
H H15B 0.5367 -0.1508 0.5326 0.039 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 . . 119.22(10) no
N1 C1 C2 . . 178.62(17) no
C7 C2 C3 . . 119.99(12) no
C7 C2 C1 . . 119.21(12) no
C3 C2 C1 . . 120.79(12) no
C4 C3 C2 . . 119.76(12) no
C4 C3 H3 . . 120.1 no
C2 C3 H3 . . 120.1 no
C3 C4 C5 . . 120.91(12) no
C3 C4 H4 . . 119.5 no
C5 C4 H4 . . 119.5 no
C4 C5 C6 . . 118.23(11) no
C4 C5 C8 . . 121.58(11) no
C6 C5 C8 . . 120.19(12) no
C7 C6 C5 . . 121.21(12) no
C7 C6 H6 . . 119.4 no
C5 C6 H6 . . 119.4 no
C6 C7 C2 . . 119.84(12) no
C6 C7 H7 . . 120.1 no
C2 C7 H7 . . 120.1 no
C9 C8 C13 . . 118.27(12) no
C9 C8 C5 . . 121.64(11) no
C13 C8 C5 . . 120.08(11) no
C10 C9 C8 . . 121.20(12) no
C10 C9 H9 . . 119.4 no
C8 C9 H9 . . 119.4 no
C11 C10 C9 . . 118.86(12) no
C11 C10 H10 . . 120.6 no
C9 C10 H10 . . 120.6 no
C12 C11 C10 . . 121.20(12) no
C12 C11 O1 . . 115.73(12) no
C10 C11 O1 . . 123.00(12) no
C11 C12 C13 . . 119.68(12) no
C11 C12 H12 . . 120.2 no
C13 C12 H12 . . 120.2 no
C12 C13 C8 . . 120.77(12) no
C12 C13 H13 . . 119.6 no
C8 C13 H13 . . 119.6 no
O2 C14 O1 . . 123.60(11) no
O2 C14 C15 . . 127.45(12) no
O1 C14 C15 . . 108.94(10) no
C14 C15 C15 . 3_656 112.44(13) no
C14 C15 H15A . . 109.1 no
C15 C15 H15A 3_656 . 109.1 no
C14 C15 H15B . . 109.1 no
C15 C15 H15B 3_656 . 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 . 1.3636(16) no
O1 C11 . 1.4032(14) no
O2 C14 . 1.1958(16) no
N1 C1 . 1.1444(18) no
C1 C2 . 1.4411(18) no
C2 C7 . 1.3913(19) no
C2 C3 . 1.3966(19) no
C3 C4 . 1.3832(17) no
C3 H3 . 0.9500 no
C4 C5 . 1.4006(18) no
C4 H4 . 0.9500 no
C5 C6 . 1.4018(19) no
C5 C8 . 1.4837(16) no
C6 C7 . 1.3776(18) no
C6 H6 . 0.9500 no
C7 H7 . 0.9500 no
C8 C9 . 1.3941(18) no
C8 C13 . 1.3943(19) no
C9 C10 . 1.3904(17) no
C9 H9 . 0.9500 no
C10 C11 . 1.3780(19) no
C10 H10 . 0.9500 no
C11 C12 . 1.377(2) no
C12 C13 . 1.3827(19) no
C12 H12 . 0.9500 no
C13 H13 . 0.9500 no
C14 C15 . 1.5009(17) no
C15 C15 3_656 1.509(2) 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 . . . . 1.0(2) no
C1 C2 C3 C4 . . . . -178.05(13) no
C2 C3 C4 C5 . . . . 1.3(2) no
C3 C4 C5 C6 . . . . -2.48(19) no
C3 C4 C5 C8 . . . . 177.59(12) no
C4 C5 C6 C7 . . . . 1.4(2) no
C8 C5 C6 C7 . . . . -178.68(12) no
C5 C6 C7 C2 . . . . 0.8(2) no
C3 C2 C7 C6 . . . . -2.0(2) no
C1 C2 C7 C6 . . . . 177.00(13) no
C4 C5 C8 C9 . . . . 34.72(19) no
C6 C5 C8 C9 . . . . -145.21(14) no
C4 C5 C8 C13 . . . . -145.76(14) no
C6 C5 C8 C13 . . . . 34.32(18) no
C13 C8 C9 C10 . . . . -1.1(2) no
C5 C8 C9 C10 . . . . 178.40(12) no
C8 C9 C10 C11 . . . . 0.4(2) no
C9 C10 C11 C12 . . . . 0.5(2) no
C9 C10 C11 O1 . . . . 177.17(12) no
C14 O1 C11 C12 . . . . -118.60(14) no
C14 O1 C11 C10 . . . . 64.53(17) no
C10 C11 C12 C13 . . . . -0.5(2) no
O1 C11 C12 C13 . . . . -177.44(12) no
C11 C12 C13 C8 . . . . -0.3(2) no
C9 C8 C13 C12 . . . . 1.1(2) no
C5 C8 C13 C12 . . . . -178.45(13) no
C11 O1 C14 O2 . . . . -13.53(19) no
C11 O1 C14 C15 . . . . 165.67(11) no
O2 C14 C15 C15 . . . 3_656 -1.0(2) no
O1 C14 C15 C15 . . . 3_656 179.81(14) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 102229918
