#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/78/7217849.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_7217849
loop_
_publ_author_name
'Chen, Hengjun'
'Li, Min'
'Zheng, Guiming'
'Wang, Yifang'
'Song, Yang'
'Han, Conghui'
'Fu, Zhiyong'
'Liao, Shijun'
'Dai, Jing-Cao'
_publ_section_title
;
 Molecular packing, crystal to crystal transformation, electron transfer
 behaviour, photochromic and fluorescent property of three hydrogen-bonded
 supramolecular complexes containing benzenecarboxylate donors and
 viologen acceptors
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA07471H
_journal_year                    2014
_chemical_formula_sum            'C27 H18 N2 O10'
_chemical_formula_weight         530.43
_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                90.00
_cell_angle_beta                 110.25(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.032(7)
_cell_length_b                   8.8150(15)
_cell_length_c                   21.444(8)
_cell_measurement_reflns_used    3936
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.99
_cell_volume                     4617(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16709
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.99
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0426
_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)+(0.0753P)²+1.1972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1275
_reflns_number_gt                2922
_reflns_number_total             3936
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra07471h2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7217849
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
O1 O 0.18916(7) 1.25066(19) 0.28417(7) 0.0564(4) Uani 1 1 d .
O2 O 0.22806(7) 1.09986(19) 0.37073(7) 0.0613(4) Uani 1 1 d .
O3 O 0.03612(6) 0.80025(16) 0.12260(6) 0.0497(4) Uani 1 1 d .
O4 O 0.01723(11) 0.60950(18) 0.17519(8) 0.0826(7) Uani 1 1 d D
O5 O 0.00840(11) 0.33995(19) 0.16784(8) 0.0838(7) Uani 1 1 d .
H3 H 0.0141(16) 0.505(2) 0.173(2) 0.120(13) Uiso 1 1 d D
O6 O 0.01485(7) 0.16271(16) 0.10118(7) 0.0544(4) Uani 1 1 d .
O7 O 0.28283(8) -0.03170(19) 0.12940(8) 0.0655(5) Uani 1 1 d .
O8 O 0.35270(8) -0.0443(2) 0.09423(9) 0.0760(5) Uani 1 1 d .
O9 O 0.37124(9) 0.0165(3) -0.00601(13) 0.0905(7) Uani 1 1 d D
H4 H 0.3698(14) -0.007(4) 0.0348(11) 0.098(11) Uiso 1 1 d D
O10 O 0.34070(8) 0.1673(2) -0.09063(10) 0.0788(6) Uani 1 1 d .
N1 N 0.06310(7) 1.0890(2) -0.25364(9) 0.0469(4) Uani 1 1 d .
H2 H 0.0527(12) 1.120(3) -0.2950(16) 0.082(9) Uiso 1 1 d .
N2 N 0.14493(6) 0.91287(17) 0.08162(7) 0.0360(4) Uani 1 1 d .
C1 C 0.06921(8) 0.9433(3) -0.23796(10) 0.0470(5) Uani 1 1 d .
H1A H 0.0619 0.8708 -0.2714 0.056 Uiso 1 1 calc R
C2 C 0.08643(8) 0.8980(2) -0.17206(9) 0.0435(5) Uani 1 1 d .
H2A H 0.0916 0.7958 -0.1608 0.052 Uiso 1 1 calc R
C3 C 0.07260(9) 1.1965(3) -0.20793(10) 0.0496(5) Uani 1 1 d .
H3A H 0.0682 1.2979 -0.2206 0.060 Uiso 1 1 calc R
C4 C 0.08884(9) 1.1588(2) -0.14203(10) 0.0469(5) Uani 1 1 d .
H4A H 0.0952 1.2343 -0.1100 0.056 Uiso 1 1 calc R
C5 C 0.09576(8) 1.0080(2) -0.12328(9) 0.0388(4) Uani 1 1 d .
C6 C 0.11246(8) 0.9685(2) -0.05184(9) 0.0376(4) Uani 1 1 d .
C7 C 0.08602(8) 1.0363(2) -0.01290(9) 0.0442(5) Uani 1 1 d .
H7A H 0.0569 1.1020 -0.0322 0.053 Uiso 1 1 calc R
C8 C 0.10267(8) 1.0070(2) 0.05342(9) 0.0421(5) Uani 1 1 d .
H8A H 0.0847 1.0523 0.0793 0.050 Uiso 1 1 calc R
C9 C 0.15462(8) 0.8687(2) -0.02215(9) 0.0424(5) Uani 1 1 d .
H9A H 0.1721 0.8195 -0.0476 0.051 Uiso 1 1 calc R
C10 C 0.17076(8) 0.8420(2) 0.04502(9) 0.0423(5) Uani 1 1 d .
H10A H 0.1994 0.7754 0.0652 0.051 Uiso 1 1 calc R
C11 C 0.16415(8) 0.8895(2) 0.15309(9) 0.0384(4) Uani 1 1 d .
C12 C 0.17026(8) 0.7425(2) 0.17707(10) 0.0444(5) Uani 1 1 d .
H12A H 0.1618 0.6602 0.1481 0.053 Uiso 1 1 calc R
C13 C 0.18921(9) 0.7207(3) 0.24502(10) 0.0509(5) Uani 1 1 d .
H13A H 0.1938 0.6229 0.2624 0.061 Uiso 1 1 calc R
C14 C 0.20133(9) 0.8439(3) 0.28711(10) 0.0494(5) Uani 1 1 d .
H14A H 0.2147 0.8280 0.3328 0.059 Uiso 1 1 calc R
C15 C 0.17510(8) 1.0143(2) 0.19439(9) 0.0394(4) Uani 1 1 d .
H15A H 0.1699 1.1121 0.1770 0.047 Uiso 1 1 calc R
C16 C 0.19413(8) 0.9903(2) 0.26295(9) 0.0419(5) Uani 1 1 d .
C17 C 0.20594(8) 1.1186(3) 0.31142(10) 0.0461(5) Uani 1 1 d .
C18 C 0.01088(9) 0.2961(2) 0.11152(9) 0.0432(5) Uani 1 1 d .
C19 C 0.00569(8) 0.4118(2) 0.05725(9) 0.0364(4) Uani 1 1 d .
C20 C 0.01255(8) 0.5702(2) 0.06258(9) 0.0364(4) Uani 1 1 d .
C21 C 0.00718(8) 0.6516(2) 0.00546(9) 0.0381(4) Uani 1 1 d .
H21A H 0.0126 0.7559 0.0094 0.046 Uiso 1 1 calc R
C22 C 0.02405(9) 0.6652(2) 0.12454(9) 0.0433(5) Uani 1 1 d .
C23 C 0.30684(10) 0.0074(2) 0.09140(10) 0.0492(5) Uani 1 1 d .
C24 C 0.27953(9) 0.1296(2) 0.04049(9) 0.0424(5) Uani 1 1 d .
C25 C 0.29444(8) 0.1805(2) -0.01348(9) 0.0429(5) Uani 1 1 d .
C26 C 0.26412(8) 0.2990(2) -0.05116(9) 0.0425(5) Uani 1 1 d .
H26A H 0.2739 0.3334 -0.0865 0.051 Uiso 1 1 calc R
C27 C 0.33771(10) 0.1190(3) -0.03928(12) 0.0548(6) Uani 1 1 d .
H1 H 0.1991(14) 1.330(4) 0.3188(17) 0.100(10) Uiso 1 1 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
C17 O1 H1 110(2) . .
C22 O4 H3 113(2) . .
C27 O9 H4 117(2) . .
C1 N1 C3 122.12(18) . .
C1 N1 H2 122(2) . .
C3 N1 H2 116(2) . .
C8 N2 C10 121.27(16) . .
C8 N2 C11 119.47(15) . .
C10 N2 C11 119.25(16) . .
N1 C1 C2 120.47(19) . .
N1 C1 H1A 119.8 . .
C2 C1 H1A 119.8 . .
C5 C2 C1 118.61(19) . .
C5 C2 H2A 120.7 . .
C1 C2 H2A 120.7 . .
N1 C3 C4 120.1(2) . .
N1 C3 H3A 119.9 . .
C4 C3 H3A 119.9 . .
C3 C4 C5 119.8(2) . .
C3 C4 H4A 120.1 . .
C5 C4 H4A 120.1 . .
C4 C5 C2 118.85(17) . .
C4 C5 C6 119.27(17) . .
C2 C5 C6 121.88(17) . .
C9 C6 C7 118.58(17) . .
C9 C6 C5 121.95(17) . .
C7 C6 C5 119.44(17) . .
C8 C7 C6 120.15(18) . .
C8 C7 H7A 119.9 . .
C6 C7 H7A 119.9 . .
N2 C8 C7 120.20(18) . .
N2 C8 H8A 119.9 . .
C7 C8 H8A 119.9 . .
C10 C9 C6 119.94(18) . .
C10 C9 H9A 120.0 . .
C6 C9 H9A 120.0 . .
N2 C10 C9 119.81(18) . .
N2 C10 H10A 120.1 . .
C9 C10 H10A 120.1 . .
C15 C11 C12 122.50(17) . .
C15 C11 N2 118.92(17) . .
C12 C11 N2 118.58(17) . .
C13 C12 C11 118.40(19) . .
C13 C12 H12A 120.8 . .
C11 C12 H12A 120.8 . .
C14 C13 C12 120.0(2) . .
C14 C13 H13A 120.0 . .
C12 C13 H13A 120.0 . .
C13 C14 C16 121.41(18) . .
C13 C14 H14A 119.3 . .
C16 C14 H14A 119.3 . .
C11 C15 C16 118.33(18) . .
C11 C15 H15A 120.8 . .
C16 C15 H15A 120.8 . .
C14 C16 C15 119.36(19) . .
C14 C16 C17 118.59(18) . .
C15 C16 C17 122.03(19) . .
O2 C17 O1 123.7(2) . .
O2 C17 C16 122.4(2) . .
O1 C17 C16 113.97(17) . .
O6 C18 O5 119.89(18) . .
O6 C18 C19 120.25(17) . .
O5 C18 C19 119.77(17) . .
C21 C19 C20 117.38(16) 5_565 .
C21 C19 C18 113.64(16) 5_565 .
C20 C19 C18 128.97(16) . .
C21 C20 C19 118.12(16) . .
C21 C20 C22 114.78(16) . .
C19 C20 C22 127.09(16) . .
C20 C21 C19 124.49(18) . 5_565
C20 C21 H21A 117.8 . .
C19 C21 H21A 117.8 5_565 .
O3 C22 O4 121.22(17) . .
O3 C22 C20 118.71(17) . .
O4 C22 C20 119.85(18) . .
O7 C23 O8 123.7(2) . .
O7 C23 C24 116.9(2) . .
O8 C23 C24 119.3(2) . .
C26 C24 C25 117.65(18) 7 .
C26 C24 C23 114.13(18) 7 .
C25 C24 C23 128.2(2) . .
C26 C25 C24 116.94(19) . .
C26 C25 C27 113.65(18) . .
C24 C25 C27 129.33(19) . .
C24 C26 C25 125.41(19) 7 .
C24 C26 H26A 117.3 7 .
C25 C26 H26A 117.3 . .
O10 C27 O9 120.5(2) . .
O10 C27 C25 119.8(2) . .
O9 C27 C25 119.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C17 1.308(3) .
O1 H1 0.99(4) .
O2 C17 1.212(2) .
O3 C22 1.235(2) .
O4 C22 1.259(3) .
O4 H3 0.928(19) .
O5 C18 1.291(2) .
O6 C18 1.208(2) .
O7 C23 1.235(3) .
O8 C23 1.259(3) .
O9 C27 1.287(3) .
O9 H4 0.913(19) .
O10 C27 1.208(3) .
N1 C1 1.323(3) .
N1 C3 1.324(3) .
N1 H2 0.88(3) .
N2 C8 1.343(3) .
N2 C10 1.350(3) .
N2 C11 1.453(2) .
C1 C2 1.385(3) .
C1 H1A 0.9300 .
C2 C5 1.385(3) .
C2 H2A 0.9300 .
C3 C4 1.368(3) .
C3 H3A 0.9300 .
C4 C5 1.382(3) .
C4 H4A 0.9300 .
C5 C6 1.482(3) .
C6 C9 1.378(3) .
C6 C7 1.388(3) .
C7 C8 1.360(3) .
C7 H7A 0.9300 .
C8 H8A 0.9300 .
C9 C10 1.374(3) .
C9 H9A 0.9300 .
C10 H10A 0.9300 .
C11 C15 1.379(3) .
C11 C12 1.383(3) .
C12 C13 1.380(3) .
C12 H12A 0.9300 .
C13 C14 1.377(3) .
C13 H13A 0.9300 .
C14 C16 1.379(3) .
C14 H14A 0.9300 .
C15 C16 1.396(3) .
C15 H15A 0.9300 .
C16 C17 1.494(3) .
C18 C19 1.518(3) .
C19 C21 1.386(3) 5_565
C19 C20 1.407(3) .
C20 C21 1.384(3) .
C20 C22 1.511(3) .
C21 C19 1.386(3) 5_565
C21 H21A 0.9300 .
C23 C24 1.523(3) .
C24 C26 1.385(3) 7
C24 C25 1.415(3) .
C25 C26 1.388(3) .
C25 C27 1.516(3) .
C26 C24 1.385(3) 7
C26 H26A 0.9300 .
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
C3 N1 C1 C2 -0.5(3) . .
N1 C1 C2 C5 1.6(3) . .
C1 N1 C3 C4 -0.6(3) . .
N1 C3 C4 C5 0.5(3) . .
C3 C4 C5 C2 0.5(3) . .
C3 C4 C5 C6 -178.98(19) . .
C1 C2 C5 C4 -1.6(3) . .
C1 C2 C5 C6 177.93(18) . .
C4 C5 C6 C9 -131.7(2) . .
C2 C5 C6 C9 48.8(3) . .
C4 C5 C6 C7 46.7(3) . .
C2 C5 C6 C7 -132.8(2) . .
C9 C6 C7 C8 1.6(3) . .
C5 C6 C7 C8 -176.73(19) . .
C10 N2 C8 C7 -1.9(3) . .
C11 N2 C8 C7 176.54(18) . .
C6 C7 C8 N2 0.3(3) . .
C7 C6 C9 C10 -2.0(3) . .
C5 C6 C9 C10 176.28(19) . .
C8 N2 C10 C9 1.5(3) . .
C11 N2 C10 C9 -176.96(18) . .
C6 C9 C10 N2 0.5(3) . .
C8 N2 C11 C15 -50.3(2) . .
C10 N2 C11 C15 128.2(2) . .
C8 N2 C11 C12 129.1(2) . .
C10 N2 C11 C12 -52.4(2) . .
C15 C11 C12 C13 -1.5(3) . .
N2 C11 C12 C13 179.18(18) . .
C11 C12 C13 C14 0.2(3) . .
C12 C13 C14 C16 1.1(3) . .
C12 C11 C15 C16 1.4(3) . .
N2 C11 C15 C16 -179.29(17) . .
C13 C14 C16 C15 -1.2(3) . .
C13 C14 C16 C17 177.5(2) . .
C11 C15 C16 C14 0.0(3) . .
C11 C15 C16 C17 -178.71(18) . .
C14 C16 C17 O2 9.6(3) . .
C15 C16 C17 O2 -171.7(2) . .
C14 C16 C17 O1 -168.88(18) . .
C15 C16 C17 O1 9.8(3) . .
O6 C18 C19 C21 14.8(3) . 5_565
O5 C18 C19 C21 -161.9(2) . 5_565
O6 C18 C19 C20 -164.7(2) . .
O5 C18 C19 C20 18.6(3) . .
C21 C19 C20 C21 -1.4(3) 5_565 .
C18 C19 C20 C21 178.08(19) . .
C21 C19 C20 C22 177.02(18) 5_565 .
C18 C19 C20 C22 -3.5(3) . .
C19 C20 C21 C19 1.5(3) . 5_565
C22 C20 C21 C19 -177.12(18) . 5_565
C21 C20 C22 O3 -11.1(3) . .
C19 C20 C22 O3 170.52(19) . .
C21 C20 C22 O4 163.6(2) . .
C19 C20 C22 O4 -14.8(3) . .
O7 C23 C24 C26 11.1(3) . 7
O8 C23 C24 C26 -166.61(19) . 7
O7 C23 C24 C25 -171.25(19) . .
O8 C23 C24 C25 11.1(3) . .
C26 C24 C25 C26 0.4(3) 7 .
C23 C24 C25 C26 -177.19(18) . .
C26 C24 C25 C27 -176.14(19) 7 .
C23 C24 C25 C27 6.2(3) . .
C24 C25 C26 C24 -0.5(3) . 7
C27 C25 C26 C24 176.64(18) . 7
C26 C25 C27 O10 -4.6(3) . .
C24 C25 C27 O10 172.0(2) . .
C26 C25 C27 O9 174.9(2) . .
C24 C25 C27 O9 -8.4(4) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199134
