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#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/04/7200492.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_7200492
loop_
_publ_author_name
'Saravanakumar, Rajendran'
'Varghese, Babu'
'Sankararaman, Sethuraman'
_publ_section_title
;
 Hydrogen-bond network in isomeric phenylenedipropynoic acids and their
 DABCO salts. Water mediated helical hydrogen bond motifs
;
_journal_coden_ASTM              CRECF4
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              337
_journal_page_last               346
_journal_paper_doi               10.1039/b816658g
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C12 H10 O6'
_chemical_formula_sum            'C12 H10 O6'
_chemical_formula_weight         250.20
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.062(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            8
_cell_length_a                   56.173(5)
_cell_length_b                   3.777(5)
_cell_length_c                   11.660(5)
_cell_measurement_reflns_used    3180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      5.832
_cell_volume                     2460(3)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       66
_diffrn_reflns_limit_h_min       -65
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11518
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.92
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9512
_exptl_absorpt_correction_T_min  0.9122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker(SADABS, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0016(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2167
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0470
_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)+(0.1117P)²+0.3936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1659
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                1752
_reflns_number_total             2167
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B816658G.txt
_cod_data_source_block           13pp
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

2018-02-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_moiety     'C24 H20 O12'
_cod_original_formula_sum        'C24 H20 O12'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     500.40
_cod_database_code               7200492
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.95303(4) -0.7835(7) 0.1188(2) 0.0605(6) Uani 1 1 d . . .
C2 C 0.93230(4) -0.6397(7) 0.0493(2) 0.0597(6) Uani 1 1 d . . .
C3 C 0.91507(3) -0.5243(6) -0.00628(18) 0.0521(6) Uani 1 1 d . . .
C4 C 0.89349(3) -0.3884(5) -0.06766(16) 0.0424(5) Uani 1 1 d . . .
C5 C 0.87265(3) -0.3943(5) -0.01459(15) 0.0397(5) Uani 1 1 d . . .
H5 H 0.8728 -0.4865 0.0595 0.048 Uiso 1 1 calc R . .
C6 C 0.85141(3) -0.2641(5) -0.07060(16) 0.0398(5) Uani 1 1 d . . .
C7 C 0.85108(4) -0.1282(5) -0.18193(16) 0.0459(5) Uani 1 1 d . . .
H7 H 0.8369 -0.0425 -0.2207 0.055 Uiso 1 1 calc R . .
C8 C 0.87194(4) -0.1228(6) -0.23363(17) 0.0507(5) Uani 1 1 d . . .
H8 H 0.8718 -0.0300 -0.3076 0.061 Uiso 1 1 calc R . .
C9 C 0.89302(4) -0.2508(6) -0.17883(18) 0.0495(5) Uani 1 1 d . . .
H9 H 0.9069 -0.2458 -0.2157 0.059 Uiso 1 1 calc R . .
C10 C 0.83032(4) -0.2602(5) -0.01139(17) 0.0473(5) Uani 1 1 d . . .
C11 C 0.81343(4) -0.2524(6) 0.04298(19) 0.0524(6) Uani 1 1 d . . .
C12 C 0.79338(4) -0.2129(6) 0.10980(18) 0.0479(5) Uani 1 1 d . . .
O1 O 0.94859(3) -0.8663(7) 0.22133(17) 0.0950(8) Uani 1 1 d . . .
H1 H 0.9607 -0.9476 0.2572 0.142 Uiso 1 1 calc R . .
O2 O 0.97194(3) -0.8237(7) 0.08257(16) 0.0871(7) Uani 1 1 d . . .
O3 O 0.79762(3) -0.3400(5) 0.21371(13) 0.0636(5) Uani 1 1 d . . .
H3 H 0.7858 -0.3123 0.2483 0.095 Uiso 1 1 calc R . .
O4 O 0.77504(3) -0.0701(5) 0.07135(13) 0.0636(5) Uani 1 1 d . . .
O5 O 0.73513(3) 0.2923(6) 0.15677(15) 0.0737(6) Uani 1 1 d D . .
O6 O 0.98249(4) -1.1529(8) 0.35093(18) 0.1027(9) Uani 1 1 d D . .
H5A H 0.7487(4) 0.164(8) 0.147(2) 0.126(14) Uiso 1 1 d D . .
H5B H 0.7297(5) 0.391(8) 0.0868(13) 0.100(10) Uiso 1 1 d D . .
H6A H 0.9789(5) -1.187(11) 0.4253(10) 0.117(13) Uiso 1 1 d D . .
H6B H 0.99883(13) -1.130(19) 0.353(3) 0.22(3) 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'
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
_geom_angle_publ_flag
O2 C1 O1 124.4(2) . . ?
O2 C1 C2 122.8(2) . . ?
O1 C1 C2 112.7(2) . . ?
C3 C2 C1 178.9(3) . . ?
C2 C3 C4 176.6(2) . . ?
C5 C4 C9 119.25(17) . . ?
C5 C4 C3 118.82(18) . . ?
C9 C4 C3 121.94(18) . . ?
C4 C5 C6 120.71(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.64(18) . . ?
C5 C6 C10 119.36(17) . . ?
C7 C6 C10 120.96(17) . . ?
C8 C7 C6 119.09(18) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.63(18) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 119.68(19) . . ?
C8 C9 H9 120.2 . . ?
C4 C9 H9 120.2 . . ?
C11 C10 C6 176.7(2) . . ?
C10 C11 C12 175.4(2) . . ?
O4 C12 O3 125.15(19) . . ?
O4 C12 C11 121.99(19) . . ?
O3 C12 C11 112.85(18) . . ?
C1 O1 H1 109.5 . . ?
C12 O3 H3 109.5 . . ?
H5A O5 H5B 108(2) . . ?
H6A O6 H6B 108(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.193(3) . ?
C1 O1 1.286(3) . ?
C1 C2 1.452(3) . ?
C2 C3 1.189(3) . ?
C3 C4 1.436(3) . ?
C4 C5 1.381(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(3) . ?
C6 C10 1.433(3) . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.196(3) . ?
C11 C12 1.443(3) . ?
C12 O4 1.207(3) . ?
C12 O3 1.301(3) . ?
O1 H1 0.8200 . ?
O3 H3 0.8200 . ?
O5 H5A 0.92(2) . ?
O5 H5B 0.92(2) . ?
O6 H6A 0.920(15) . ?
O6 H6B 0.920(13) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O6 0.82 1.74 2.545(3) 168.8 .
O3 H3 O5 0.82 1.74 2.550(2) 167.8 4_645
O5 H5A O4 0.92(2) 2.009(10) 2.892(2) 161(3) .
O5 H5B O4 0.92(2) 1.955(7) 2.860(3) 167(3) 7_655
O6 H6A O2 0.920(15) 1.915(7) 2.827(3) 171(4) 6_536
O6 H6B O2 0.920(13) 2.08(4) 2.878(3) 144(6) 2_755
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 160(14) . . . . ?
O1 C1 C2 C3 -19(14) . . . . ?
C1 C2 C3 C4 18(17) . . . . ?
C2 C3 C4 C5 -4(4) . . . . ?
C2 C3 C4 C9 176(4) . . . . ?
C9 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 C6 179.72(18) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C10 -177.36(17) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C10 C6 C7 C8 177.12(18) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
C5 C4 C9 C8 0.2(3) . . . . ?
C3 C4 C9 C8 -179.7(2) . . . . ?
C5 C6 C10 C11 38(4) . . . . ?
C7 C6 C10 C11 -140(4) . . . . ?
C6 C10 C11 C12 65(5) . . . . ?
C10 C11 C12 O4 73(3) . . . . ?
C10 C11 C12 O3 -106(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168353923
