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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/4/50/80/4508094.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_4508094
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_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                 94.553(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.9716(3)
_cell_length_b                   10.8431(4)
_cell_length_c                   18.2505(6)
_cell_measurement_reflns_used    2063
_cell_measurement_temperature    228(2)
_cell_measurement_theta_max      28.5760
_cell_measurement_theta_min      3.7360
_cell_volume                     1375.27(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      228(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.9906
_diffrn_measured_fraction_theta_max 0.8526
_diffrn_measurement_details
;
  1 omega  -86.00    2.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000   60.0000 88

  2 omega  -17.00   20.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000   90.0000 37

  3 omega  -84.00    4.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -57.0000  150.0000 88

  4 omega  -38.00   15.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000 -150.0000 53
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0055115000
_diffrn_orient_matrix_UB_12      -0.0060267000
_diffrn_orient_matrix_UB_13      0.0384789000
_diffrn_orient_matrix_UB_21      -0.1018009000
_diffrn_orient_matrix_UB_22      0.0033064000
_diffrn_orient_matrix_UB_23      -0.0049989000
_diffrn_orient_matrix_UB_31      -0.0046658000
_diffrn_orient_matrix_UB_32      -0.0650481000
_diffrn_orient_matrix_UB_33      -0.0038413000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0314
_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       -24
_diffrn_reflns_number            7045
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.14
_diffrn_reflns_theta_min         3.73
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98549
_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    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0422
_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)+(0.0430P)²+0.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                2431
_reflns_number_total             3165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4009174_si_002.cif
_cod_data_source_block           P21-228
_cod_original_cell_volume        1375.28(9)
_cod_database_code               4508094
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 0.45471(19) 0.36223(10) 0.35861(6) 0.0439(3) Uani 1 1 d .
O4 O 0.29601(18) 0.74154(10) 0.40784(6) 0.0390(3) Uani 1 1 d D
O3 O 0.13130(17) 0.57109(12) 0.42987(7) 0.0475(3) Uani 1 1 d .
O2 O 0.54694(19) 0.54936(10) 0.32610(5) 0.0414(3) Uani 1 1 d D
C4 C 0.5212(2) 0.46256(13) 0.37418(7) 0.0283(3) Uani 1 1 d .
C3 C 0.5845(2) 0.50153(13) 0.45208(7) 0.0265(3) Uani 1 1 d .
H3 H 0.7194 0.5308 0.4561 0.032 Uiso 1 1 calc R
C1 C 0.2733(2) 0.63407(13) 0.43985(7) 0.0289(3) Uani 1 1 d .
C2 C 0.4487(2) 0.59537(13) 0.48866(7) 0.0263(3) Uani 1 1 d .
H2A H 0.5208 0.6675 0.5095 0.032 Uiso 1 1 calc R
N1 N 0.58426(19) 0.98631(12) 0.30566(6) 0.0334(3) Uani 1 1 d .
N2 N 1.10492(19) 0.75834(12) 0.77648(6) 0.0331(3) Uani 1 1 d .
C7 C 0.7373(2) 0.93396(13) 0.44803(7) 0.0274(3) Uani 1 1 d .
C8 C 0.6562(2) 1.04784(14) 0.42993(8) 0.0309(3) Uani 1 1 d .
H8 H 0.6516 1.1094 0.4660 0.037 Uiso 1 1 calc R
C5 C 0.6638(2) 0.87661(14) 0.32242(8) 0.0367(4) Uani 1 1 d .
H5 H 0.6667 0.8171 0.2851 0.044 Uiso 1 1 calc R
C14 C 1.1290(2) 0.67439(14) 0.72472(8) 0.0359(4) Uani 1 1 d .
H14 H 1.2011 0.6034 0.7379 0.043 Uiso 1 1 calc R
C6 C 0.7419(2) 0.84671(14) 0.39219(8) 0.0340(4) Uani 1 1 d .
H6 H 0.7972 0.7687 0.4018 0.041 Uiso 1 1 calc R
C12 C 0.9531(2) 0.79139(13) 0.63080(7) 0.0283(3) Uani 1 1 d .
C13 C 1.0536(2) 0.68621(14) 0.65272(8) 0.0349(4) Uani 1 1 d .
H13 H 1.0706 0.6228 0.6187 0.042 Uiso 1 1 calc R
C9 C 0.5822(2) 1.07062(14) 0.35886(8) 0.0325(3) Uani 1 1 d .
H9 H 0.5283 1.1484 0.3475 0.039 Uiso 1 1 calc R
C11 C 0.8807(2) 0.80747(14) 0.55348(7) 0.0309(3) Uani 1 1 d .
H11 H 0.8834 0.7386 0.5223 0.037 Uiso 1 1 calc R
C16 C 0.9289(3) 0.87924(16) 0.68477(8) 0.0419(4) Uani 1 1 d .
H16 H 0.8607 0.9523 0.6729 0.050 Uiso 1 1 calc R
C10 C 0.8117(2) 0.91222(14) 0.52476(7) 0.0306(3) Uani 1 1 d .
H10 H 0.8101 0.9800 0.5568 0.037 Uiso 1 1 calc R
C15 C 1.0052(3) 0.85882(16) 0.75595(9) 0.0432(4) Uani 1 1 d .
H15 H 0.9857 0.9190 0.7917 0.052 Uiso 1 1 calc R
H4 H 0.219(3) 0.743(2) 0.3666(11) 0.087(8) Uiso 1 1 d D
H2 H 0.498(3) 0.525(2) 0.2785(9) 0.081(7) 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 108.0(16) . .
C4 O2 H2 111.1(14) . .
O1 C4 O2 124.09(12) . .
O1 C4 C3 123.36(13) . .
O2 C4 C3 112.55(12) . .
C4 C3 H3 111.2 . .
C4 C3 C2 115.99(11) . .
C4 C3 C2 114.86(11) . 3_666
C2 C3 H3 111.2 3_666 .
C2 C3 H3 111.2 . .
C2 C3 C2 90.83(10) 3_666 .
O4 C1 C2 112.69(13) . .
O3 C1 O4 124.07(13) . .
O3 C1 C2 123.20(13) . .
C3 C2 C3 89.17(10) 3_666 .
C3 C2 H2A 111.7 . .
C3 C2 H2A 111.7 3_666 .
C1 C2 C3 114.49(11) . .
C1 C2 C3 116.34(12) . 3_666
C1 C2 H2A 111.7 . .
C9 N1 C5 118.11(12) . .
C15 N2 C14 116.90(12) . .
C8 C7 C6 117.59(13) . .
C8 C7 C10 118.35(13) . .
C6 C7 C10 124.06(13) . .
C7 C8 H8 120.1 . .
C9 C8 C7 119.89(13) . .
C9 C8 H8 120.1 . .
N1 C5 H5 118.5 . .
N1 C5 C6 123.01(14) . .
C6 C5 H5 118.5 . .
N2 C14 H14 118.3 . .
N2 C14 C13 123.44(14) . .
C13 C14 H14 118.3 . .
C7 C6 H6 120.5 . .
C5 C6 C7 118.96(14) . .
C5 C6 H6 120.5 . .
C13 C12 C11 120.23(13) . .
C13 C12 C16 116.63(13) . .
C16 C12 C11 123.14(14) . .
C14 C13 H13 120.1 . .
C12 C13 C14 119.87(14) . .
C12 C13 H13 120.1 . .
N1 C9 C8 122.44(14) . .
N1 C9 H9 118.8 . .
C8 C9 H9 118.8 . .
C12 C11 H11 117.7 . .
C10 C11 C12 124.55(14) . .
C10 C11 H11 117.7 . .
C12 C16 H16 120.1 . .
C15 C16 C12 119.78(14) . .
C15 C16 H16 120.1 . .
C7 C10 H10 116.5 . .
C11 C10 C7 127.04(14) . .
C11 C10 H10 116.5 . .
N2 C15 C16 123.35(14) . .
N2 C15 H15 118.3 . .
C16 C15 H15 118.3 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.2076(17) .
O4 C1 1.3187(17) .
O4 H4 0.888(16) .
O3 C1 1.2044(18) .
O2 C4 1.3088(17) .
O2 H2 0.943(16) .
C4 C3 1.5149(17) .
C3 H3 0.9900 .
C3 C2 1.5384(19) 3_666
C3 C2 1.574(2) .
C1 C2 1.5139(19) .
C2 C3 1.5385(19) 3_666
C2 H2A 0.9900 .
N1 C5 1.338(2) .
N1 C9 1.3345(19) .
N2 C14 1.332(2) .
N2 C15 1.330(2) .
C7 C8 1.387(2) .
C7 C6 1.393(2) .
C7 C10 1.4734(18) .
C8 H8 0.9400 .
C8 C9 1.3796(19) .
C5 H5 0.9400 .
C5 C6 1.383(2) .
C14 H14 0.9400 .
C14 C13 1.382(2) .
C6 H6 0.9400 .
C12 C13 1.381(2) .
C12 C11 1.4710(18) .
C12 C16 1.390(2) .
C13 H13 0.9400 .
C9 H9 0.9400 .
C11 H11 0.9400 .
C11 C10 1.325(2) .
C16 H16 0.9400 .
C16 C15 1.382(2) .
C10 H10 0.9400 .
C15 H15 0.9400 .
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 -2.0(2) . 3_666
O1 C4 C3 C2 -106.12(17) . .
O4 C1 C2 C3 159.39(12) . 3_666
O4 C1 C2 C3 -98.62(14) . .
O3 C1 C2 C3 -22.8(2) . 3_666
O3 C1 C2 C3 79.18(19) . .
O2 C4 C3 C2 73.94(17) . .
O2 C4 C3 C2 178.05(13) . 3_666
C4 C3 C2 C3 118.35(14) . 3_666
C4 C3 C2 C1 -0.40(18) . .
C2 C3 C2 C3 0.0 3_666 3_666
C2 C3 C2 C1 -118.75(14) 3_666 .
N1 C5 C6 C7 0.4(3) . .
N2 C14 C13 C12 2.4(3) . .
C7 C8 C9 N1 0.3(2) . .
C8 C7 C6 C5 -1.0(2) . .
C8 C7 C10 C11 174.67(16) . .
C5 N1 C9 C8 -0.9(2) . .
C14 N2 C15 C16 -0.4(3) . .
C6 C7 C8 C9 0.6(2) . .
C6 C7 C10 C11 -4.9(3) . .
C12 C11 C10 C7 -179.98(14) . .
C12 C16 C15 N2 0.8(3) . .
C13 C12 C11 C10 -168.26(16) . .
C13 C12 C16 C15 0.5(2) . .
C9 N1 C5 C6 0.5(2) . .
C11 C12 C13 C14 176.94(14) . .
C11 C12 C16 C15 -178.40(16) . .
C16 C12 C13 C14 -2.0(2) . .
C16 C12 C11 C10 10.6(3) . .
C10 C7 C8 C9 -178.92(14) . .
C10 C7 C6 C5 178.58(15) . .
C15 N2 C14 C13 -1.2(2) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139040776
