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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/80/4508091.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_4508091
loop_
_publ_author_name
'Bhattacharya, Suman'
'Saha, Binoy K.'
_publ_section_title
;
 Interaction Dependence and Similarity in Thermal Expansion of a Dimorphic
 1D Hydrogen-Bonded Organic Complex
;
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3299
_journal_paper_doi               10.1021/cg4009174
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C8 H8 O8, 2(C12 H10 N2)'
_chemical_formula_sum            'C32 H28 N4 O8'
_chemical_formula_weight         596.58
_chemical_name_common            'CBTA.BPE Form-I'
_chemical_name_systematic
;
cyclobutane-1,2,3,4-tetracarboxylic acid,
(E)-1,2-di(pyridin-4-yl)ethene complex polymorph I
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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_date             2013-04-18
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr  9 2013 14:06:00, GUI svn.r4458)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.223(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.8748(3)
_cell_length_b                   10.7986(4)
_cell_length_c                   18.2305(7)
_cell_measurement_reflns_used    2130
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.0120
_cell_measurement_theta_min      3.7630
_cell_volume                     1349.73(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9880
_diffrn_measured_fraction_theta_max 0.8502
_diffrn_measurement_details
;
  1 omega   -5.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000    0.0000 28

  2 omega  -86.00    4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000   60.0000 90

  3 omega  -85.00    3.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  150.0000 88

  4 omega  -38.00   19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000 -180.0000 57
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0058466000
_diffrn_orient_matrix_UB_12      -0.0059782000
_diffrn_orient_matrix_UB_13      0.0385242000
_diffrn_orient_matrix_UB_21      -0.1032445000
_diffrn_orient_matrix_UB_22      0.0024979000
_diffrn_orient_matrix_UB_23      -0.0049332000
_diffrn_orient_matrix_UB_31      -0.0034491000
_diffrn_orient_matrix_UB_32      -0.0653468000
_diffrn_orient_matrix_UB_33      -0.0037408000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6885
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.17
_diffrn_reflns_theta_min         3.76
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0395
_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)+(0.0406P)²+0.4706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                2555
_reflns_number_total             3106
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4009174_si_002.cif
_cod_data_source_block           P21-120
_cod_original_cell_volume        1349.73(10)
_cod_database_code               4508091
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.45265(15) 0.36116(9) 0.35849(5) 0.0236(2) Uani 1 1 d .
O4 O 0.29575(15) 0.74383(9) 0.40807(5) 0.0216(2) Uani 1 1 d D
O3 O 0.12810(15) 0.57130(9) 0.42930(6) 0.0253(2) Uani 1 1 d .
O2 O 0.54602(15) 0.55046(9) 0.32597(5) 0.0230(2) Uani 1 1 d D
C4 C 0.52049(19) 0.46236(12) 0.37401(7) 0.0162(3) Uani 1 1 d .
C3 C 0.58606(19) 0.50098(12) 0.45193(7) 0.0151(3) Uani 1 1 d .
H3 H 0.7246 0.5299 0.4556 0.018 Uiso 1 1 calc R
C1 C 0.2722(2) 0.63514(12) 0.43981(7) 0.0163(3) Uani 1 1 d .
C2 C 0.44886(19) 0.59624(11) 0.48886(7) 0.0149(3) Uani 1 1 d .
H2A H 0.5232 0.6693 0.5098 0.018 Uiso 1 1 calc R
N1 N 0.58604(16) 0.98644(11) 0.30500(6) 0.0191(3) Uani 1 1 d .
N2 N 1.10721(17) 0.75798(10) 0.77637(6) 0.0186(3) Uani 1 1 d .
C7 C 0.73837(18) 0.93348(12) 0.44773(7) 0.0163(3) Uani 1 1 d .
C8 C 0.65581(19) 1.04826(12) 0.42966(7) 0.0179(3) Uani 1 1 d .
H8 H 0.6504 1.1106 0.4662 0.021 Uiso 1 1 calc R
C5 C 0.6670(2) 0.87566(13) 0.32152(7) 0.0208(3) Uani 1 1 d .
H5 H 0.6710 0.8154 0.2837 0.025 Uiso 1 1 calc R
C14 C 1.1319(2) 0.67272(12) 0.72463(7) 0.0195(3) Uani 1 1 d .
H14 H 1.2057 0.6007 0.7380 0.023 Uiso 1 1 calc R
C6 C 0.7448(2) 0.84601(12) 0.39160(7) 0.0192(3) Uani 1 1 d .
H6 H 0.8019 0.7670 0.4013 0.023 Uiso 1 1 calc R
C12 C 0.95389(19) 0.79051(12) 0.63058(7) 0.0166(3) Uani 1 1 d .
C13 C 1.0551(2) 0.68427(12) 0.65256(7) 0.0194(3) Uani 1 1 d .
H13 H 1.0717 0.6195 0.6183 0.023 Uiso 1 1 calc R
C9 C 0.5818(2) 1.07129(12) 0.35837(7) 0.0187(3) Uani 1 1 d .
H9 H 0.5260 1.1501 0.3469 0.022 Uiso 1 1 calc R
C11 C 0.88131(19) 0.80597(13) 0.55330(7) 0.0175(3) Uani 1 1 d .
H11 H 0.8836 0.7358 0.5219 0.021 Uiso 1 1 calc R
C16 C 0.9292(2) 0.87977(13) 0.68462(7) 0.0226(3) Uani 1 1 d .
H16 H 0.8599 0.9540 0.6725 0.027 Uiso 1 1 calc R
C10 C 0.81234(19) 0.91212(13) 0.52427(7) 0.0177(3) Uani 1 1 d .
H10 H 0.8110 0.9811 0.5566 0.021 Uiso 1 1 calc R
C15 C 1.0060(2) 0.85948(13) 0.75578(8) 0.0242(3) Uani 1 1 d .
H15 H 0.9860 0.9207 0.7919 0.029 Uiso 1 1 calc R
H4 H 0.217(3) 0.7448(19) 0.3665(10) 0.056(6) Uiso 1 1 d D
H2 H 0.495(3) 0.525(2) 0.2791(10) 0.076(8) Uiso 1 1 d D
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O4 H4 107.1(13) . .
C4 O2 H2 109.6(15) . .
O1 C4 O2 124.39(12) . .
O1 C4 C3 123.27(12) . .
O2 C4 C3 112.34(11) . .
C4 C3 H3 111.3 . .
C4 C3 C2 115.64(10) . .
C4 C3 C2 114.76(10) . 3_666
C2 C3 H3 111.3 3_666 .
C2 C3 H3 111.3 . .
C2 C3 C2 90.94(9) 3_666 .
O4 C1 C2 112.70(11) . .
O3 C1 O4 124.10(12) . .
O3 C1 C2 123.17(12) . .
C3 C2 C3 89.06(9) 3_666 .
C3 C2 H2A 111.8 . .
C3 C2 H2A 111.8 3_666 .
C1 C2 C3 114.03(10) . .
C1 C2 C3 116.39(11) . 3_666
C1 C2 H2A 111.8 . .
C9 N1 C5 118.51(11) . .
C15 N2 C14 117.16(11) . .
C8 C7 C6 117.61(12) . .
C8 C7 C10 118.13(12) . .
C6 C7 C10 124.27(12) . .
C7 C8 H8 120.1 . .
C9 C8 C7 119.85(12) . .
C9 C8 H8 120.1 . .
N1 C5 H5 118.7 . .
N1 C5 C6 122.51(12) . .
C6 C5 H5 118.7 . .
N2 C14 H14 118.4 . .
N2 C14 C13 123.20(13) . .
C13 C14 H14 118.4 . .
C7 C6 H6 120.4 . .
C5 C6 C7 119.25(12) . .
C5 C6 H6 120.4 . .
C13 C12 C11 119.95(12) . .
C13 C12 C16 116.85(12) . .
C16 C12 C11 123.19(12) . .
C14 C13 C12 119.81(12) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
N1 C9 C8 122.26(12) . .
N1 C9 H9 118.9 . .
C8 C9 H9 118.9 . .
C12 C11 H11 117.9 . .
C10 C11 C12 124.29(12) . .
C10 C11 H11 117.9 . .
C12 C16 H16 120.2 . .
C15 C16 C12 119.64(13) . .
C15 C16 H16 120.2 . .
C7 C10 H10 116.6 . .
C11 C10 C7 126.87(12) . .
C11 C10 H10 116.6 . .
N2 C15 C16 123.28(13) . .
N2 C15 H15 118.4 . .
C16 C15 H15 118.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.2134(16) .
O4 C1 1.3237(16) .
O4 H4 0.898(15) .
O3 C1 1.2107(16) .
O2 C4 1.3136(16) .
O2 H2 0.940(16) .
C4 C3 1.5168(17) .
C3 H3 1.0000 .
C3 C2 1.5372(17) 3_666
C3 C2 1.5794(18) .
C1 C2 1.5135(17) .
C2 C3 1.5372(17) 3_666
C2 H2A 1.0000 .
N1 C5 1.3441(18) .
N1 C9 1.3384(17) .
N2 C14 1.3379(18) .
N2 C15 1.3370(18) .
C7 C8 1.3926(18) .
C7 C6 1.3957(18) .
C7 C10 1.4678(17) .
C8 H8 0.9500 .
C8 C9 1.3829(18) .
C5 H5 0.9500 .
C5 C6 1.3859(18) .
C14 H14 0.9500 .
C14 C13 1.3850(18) .
C6 H6 0.9500 .
C12 C13 1.3856(19) .
C12 C11 1.4692(17) .
C12 C16 1.3975(19) .
C13 H13 0.9500 .
C9 H9 0.9500 .
C11 H11 0.9500 .
C11 C10 1.3348(19) .
C16 H16 0.9500 .
C16 C15 1.3816(18) .
C10 H10 0.9500 .
C15 H15 0.9500 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
O1 C4 C3 C2 -2.79(19) . 3_666
O1 C4 C3 C2 -106.75(15) . .
O4 C1 C2 C3 158.96(11) . 3_666
O4 C1 C2 C3 -99.42(13) . .
O3 C1 C2 C3 -23.21(18) . 3_666
O3 C1 C2 C3 78.41(16) . .
O2 C4 C3 C2 73.37(15) . .
O2 C4 C3 C2 177.33(11) . 3_666
C4 C3 C2 C3 118.20(13) . 3_666
C4 C3 C2 C1 -0.45(16) . .
C2 C3 C2 C3 0.0 3_666 3_666
C2 C3 C2 C1 -118.65(13) 3_666 .
N1 C5 C6 C7 0.5(2) . .
N2 C14 C13 C12 2.8(2) . .
C7 C8 C9 N1 0.0(2) . .
C8 C7 C6 C5 -1.1(2) . .
C8 C7 C10 C11 174.17(13) . .
C5 N1 C9 C8 -0.7(2) . .
C14 N2 C15 C16 -0.6(2) . .
C6 C7 C8 C9 0.85(19) . .
C6 C7 C10 C11 -5.7(2) . .
C12 C11 C10 C7 179.87(12) . .
C12 C16 C15 N2 0.9(2) . .
C13 C12 C11 C10 -168.13(13) . .
C13 C12 C16 C15 0.5(2) . .
C9 N1 C5 C6 0.4(2) . .
C11 C12 C13 C14 176.72(12) . .
C11 C12 C16 C15 -178.41(13) . .
C16 C12 C13 C14 -2.3(2) . .
C16 C12 C11 C10 10.8(2) . .
C10 C7 C8 C9 -179.02(12) . .
C10 C7 C6 C5 178.76(13) . .
C15 N2 C14 C13 -1.3(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040776
