#------------------------------------------------------------------------------
#$Date: 2026-05-05 11:04:05 +0200 (Tue, 05 May 2026) $
#$Revision: 305789 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/25/16/7251623.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_7251623
loop_
_publ_author_name
'Kuz'mina, Lyudmila G.'
'Vedernikov, Artem I.'
'Sazonov, Sergey K.'
'Aleksandrova, Nadezhda A.'
'Alfimov, Michael V.'
'Gromov, Sergey P.'
_publ_section_title
;
 Study of the influence of anion nature on crystal packing features and
 feasibility of [2 + 2] photocycloaddition reaction in protonated forms of
 dimethoxystyrylheterocycles
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2560
_journal_page_last               2577
_journal_paper_doi               10.1039/D5CE01173F
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C30 H32 N2 O4, 2(C6 H2 N3 O7)'
_chemical_formula_sum            'C42 H36 N8 O18'
_chemical_formula_weight         940.79
_chemical_name_systematic
'4,4'-[c-2,t-4-bis(3,4-dimethoxyphenyl)cyclobutane-r-1,t-3-diyl]dipyridinium bis(2,4,6-trinitrobenzenolate)'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2025-10-10 deposited with the CCDC.	2026-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                100.660(2)
_cell_angle_beta                 100.472(2)
_cell_angle_gamma                106.479(2)
_cell_formula_units_Z            1
_cell_length_a                   9.6794(5)
_cell_length_b                   9.7835(5)
_cell_length_c                   12.1156(6)
_cell_measurement_reflns_used    3553
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      59.530
_cell_measurement_theta_min      4.531
_cell_volume                     1047.28(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       /W
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13568
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.243
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     192
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0653P)²+0.3062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3353
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce01173f2.cif
_cod_data_source_block           pp_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7251618--7251632.cif.'
_cod_database_code               7251623
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.998
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.86616(16) 0.93088(16) 0.22744(13) 0.0278(4) Uani 1 1 d . . . . .
N1 N 0.2930(2) -0.0384(2) 0.27772(16) 0.0249(4) Uani 1 1 d D . . . .
H1 H 0.245(3) -0.132(3) 0.236(2) 0.042(7) Uiso 1 1 d . . . . .
O2 O 0.9833(7) 0.8433(7) 0.4017(7) 0.0257(10) Uani 0.710(5) 1 d . U P A 1
C1 C 0.4267(9) -0.0021(8) 0.3514(9) 0.0226(13) Uani 0.710(5) 1 d D U P A 1
H1B H 0.4691 -0.0762 0.3633 0.027 Uiso 0.710(5) 1 calc R U P A 1
C2 C 0.5014(5) 0.1409(5) 0.4089(4) 0.0224(9) Uani 0.710(5) 1 d D U P A 1
H2A H 0.5963 0.1662 0.4607 0.027 Uiso 0.710(5) 1 calc R U P A 1
C3 C 0.4403(5) 0.2510(4) 0.3927(3) 0.0164(8) Uani 0.710(5) 1 d D U P A 1
C4 C 0.3019(6) 0.2080(6) 0.3158(5) 0.0232(11) Uani 0.710(5) 1 d D U P A 1
H4A H 0.2569 0.2799 0.3019 0.028 Uiso 0.710(5) 1 calc R U P A 1
C5 C 0.2284(12) 0.0610(7) 0.2589(12) 0.0281(11) Uani 0.710(5) 1 d D U P A 1
H5A H 0.1330 0.0317 0.2070 0.034 Uiso 0.710(5) 1 calc R U P A 1
C6 C 0.5289(3) 0.4075(3) 0.4547(2) 0.0164(7) Uani 0.710(5) 1 d . U P A 1
H6A H 0.6358 0.4243 0.4548 0.020 Uiso 0.710(5) 1 calc R U P A 1
C7 C 0.4824(3) 0.5346(3) 0.4172(2) 0.0161(7) Uani 0.710(5) 1 d . U P A 1
H7A H 0.3804 0.4934 0.3640 0.019 Uiso 0.710(5) 1 calc R U P A 1
C8 C 0.5855(3) 0.6353(2) 0.3633(2) 0.0160(7) Uani 0.710(5) 1 d G U P A 1
C9 C 0.5236(3) 0.6786(3) 0.2685(3) 0.0205(8) Uani 0.710(5) 1 d G U P A 1
H9A H 0.4191 0.6418 0.2365 0.025 Uiso 0.710(5) 1 calc R U P A 1
C10 C 0.6146(4) 0.7755(4) 0.2204(3) 0.0219(9) Uani 0.710(5) 1 d G U P A 1
H10A H 0.5723 0.8050 0.1555 0.026 Uiso 0.710(5) 1 calc R U P A 1
C11 C 0.7675(3) 0.8293(5) 0.2672(4) 0.0204(12) Uani 0.710(5) 1 d G U P A 1
C12 C 0.8294(3) 0.7861(4) 0.3620(3) 0.0209(9) Uani 0.710(5) 1 d G U P A 1
C13 C 0.7384(4) 0.6891(3) 0.4101(2) 0.0194(8) Uani 0.710(5) 1 d G U P A 1
H13A H 0.7808 0.6596 0.4750 0.023 Uiso 0.710(5) 1 calc R U P A 1
C15 C 1.0459(5) 0.8235(5) 0.5100(4) 0.0273(9) Uani 0.710(5) 1 d . U P A 1
H15A H 1.1526 0.8789 0.5337 0.041 Uiso 0.710(5) 1 calc R U P A 1
H15B H 1.0310 0.7186 0.5032 0.041 Uiso 0.710(5) 1 calc R U P A 1
H15C H 0.9975 0.8592 0.5682 0.041 Uiso 0.710(5) 1 calc R U P A 1
O2' O 1.0188(19) 0.8754(19) 0.3973(17) 0.030(3) Uani 0.290(5) 1 d . U P A 2
C1' C 0.420(2) 0.0321(17) 0.361(2) 0.031(5) Uani 0.290(5) 1 d D U P A 2
H1'A H 0.4800 -0.0234 0.3865 0.038 Uiso 0.290(5) 1 calc R U P A 2
C2' C 0.4658(11) 0.1795(11) 0.4107(8) 0.015(2) Uani 0.290(5) 1 d D U P A 2
H2'A H 0.5563 0.2258 0.4689 0.018 Uiso 0.290(5) 1 calc R U P A 2
C3' C 0.3786(12) 0.2600(10) 0.3747(8) 0.0105(17) Uani 0.290(5) 1 d D U P A 2
C4' C 0.2443(12) 0.1852(15) 0.2939(12) 0.021(3) Uani 0.290(5) 1 d D U P A 2
H4'A H 0.1768 0.2360 0.2738 0.026 Uiso 0.290(5) 1 calc R U P A 2
C5' C 0.208(3) 0.040(2) 0.243(3) 0.0281(11) Uani 0.290(5) 1 d D . P A 2
H5'A H 0.1212 -0.0073 0.1820 0.034 Uiso 0.290(5) 1 calc R U P A 2
C6' C 0.4213(7) 0.4235(7) 0.4181(5) 0.0160(18) Uani 0.290(5) 1 d . U P A 2
H6'A H 0.3655 0.4643 0.3621 0.019 Uiso 0.290(5) 1 calc R U P A 2
C7' C 0.5884(8) 0.5141(7) 0.4535(6) 0.0171(18) Uani 0.290(5) 1 d . U P A 2
H7'A H 0.6471 0.4450 0.4556 0.021 Uiso 0.290(5) 1 calc R U P A 2
C8' C 0.6518(8) 0.6253(6) 0.3875(5) 0.0134(16) Uani 0.290(5) 1 d G U P A 2
C9' C 0.5679(7) 0.6577(7) 0.2962(6) 0.0135(17) Uani 0.290(5) 1 d G U P A 2
H9'A H 0.4635 0.6087 0.2709 0.016 Uiso 0.290(5) 1 calc R U P A 2
C10' C 0.6367(9) 0.7616(10) 0.2420(7) 0.020(2) Uani 0.290(5) 1 d G U P A 2
H10B H 0.5793 0.7837 0.1796 0.024 Uiso 0.290(5) 1 calc R U P A 2
C11' C 0.7894(9) 0.8332(11) 0.2790(9) 0.025(3) Uani 0.290(5) 1 d G U P A 2
C12' C 0.8733(7) 0.8009(10) 0.3703(8) 0.0113(18) Uani 0.290(5) 1 d G U P A 2
C13' C 0.8045(8) 0.6969(8) 0.4246(5) 0.0176(19) Uani 0.290(5) 1 d G U P A 2
H13B H 0.8618 0.6749 0.4870 0.021 Uiso 0.290(5) 1 calc R U P A 2
C15' C 1.1084(12) 0.8660(12) 0.5067(9) 0.029(2) Uani 0.290(5) 1 d . U P A 2
H15D H 1.2100 0.9342 0.5227 0.043 Uiso 0.290(5) 1 calc R U P A 2
H15E H 1.1107 0.7653 0.4993 0.043 Uiso 0.290(5) 1 calc R U P A 2
H15F H 1.0638 0.8924 0.5704 0.043 Uiso 0.290(5) 1 calc R U P A 2
C14 C 0.7965(3) 0.9934(3) 0.1448(2) 0.0387(6) Uani 1 1 d . . . . .
H14A H 0.8728 1.0688 0.1256 0.058 Uiso 1 1 calc R U . . .
H14B H 0.7296 1.0382 0.1778 0.058 Uiso 1 1 calc R U . . .
H14C H 0.7392 0.9159 0.0743 0.058 Uiso 1 1 calc R U . . .
O1P O 1.12982(16) 0.71237(15) 0.12994(12) 0.0261(3) Uani 1 1 d . . . . .
O2P O 0.9484(2) 0.80803(18) -0.01790(14) 0.0380(4) Uani 1 1 d . . . . .
O3P O 0.80354(17) 0.60531(17) -0.14014(12) 0.0293(4) Uani 1 1 d . . . . .
O4P O 0.47387(16) 0.31883(18) 0.06188(13) 0.0326(4) Uani 1 1 d . . . . .
O5P O 0.58464(17) 0.24143(19) 0.19746(14) 0.0366(4) Uani 1 1 d . . . . .
O6P O 1.09557(17) 0.47276(18) 0.37555(13) 0.0340(4) Uani 1 1 d . . . . .
O7P O 1.21966(16) 0.67606(17) 0.34321(13) 0.0306(4) Uani 1 1 d . . . . .
N1P N 0.87528(19) 0.67722(19) -0.04214(14) 0.0230(4) Uani 1 1 d . . . . .
N2P N 0.58586(19) 0.3223(2) 0.13046(15) 0.0243(4) Uani 1 1 d . . . . .
N3P N 1.10799(19) 0.56663(19) 0.31883(15) 0.0237(4) Uani 1 1 d . . . . .
C1P C 1.0070(2) 0.6304(2) 0.13639(17) 0.0191(4) Uani 1 1 d . . . . .
C2P C 0.8702(2) 0.6008(2) 0.05114(16) 0.0193(4) Uani 1 1 d . . . . .
C3P C 0.7366(2) 0.5033(2) 0.04683(16) 0.0201(4) Uani 1 1 d . . . . .
H3PA H 0.6514 0.4878 -0.0133 0.024 Uiso 1 1 calc R U . . .
C4P C 0.7275(2) 0.4265(2) 0.13293(16) 0.0192(4) Uani 1 1 d . . . . .
C5P C 0.8505(2) 0.4475(2) 0.21965(17) 0.0202(4) Uani 1 1 d . . . . .
H5PA H 0.8428 0.3933 0.2770 0.024 Uiso 1 1 calc R U . . .
C6P C 0.9848(2) 0.5476(2) 0.22290(16) 0.0198(4) Uani 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
_geom_angle_publ_flag
C11' O1 C14 123.4(4) . . ?
C11 O1 C14 114.4(2) . . ?
C5 N1 C1 122.2(4) . . ?
C5' N1 C1' 118.3(11) . . ?
C12 O2 C15 116.7(4) . . ?
N1 C1 C2 120.0(6) . . ?
C1 C2 C3 120.6(5) . . ?
C4 C3 C2 117.2(4) . . ?
C4 C3 C6 123.9(4) . . ?
C2 C3 C6 118.8(4) . . ?
C3 C4 C5 120.6(5) . . ?
N1 C5 C4 119.3(6) . . ?
C3 C6 C7 119.9(3) . . ?
C3 C6 C7 117.7(2) . 2_666 ?
C7 C6 C7 90.7(2) . 2_666 ?
C8 C7 C6 118.1(2) . . ?
C8 C7 C6 119.9(2) . 2_666 ?
C6 C7 C6 89.3(2) . 2_666 ?
C9 C8 C13 120.0 . . ?
C9 C8 C7 118.7(2) . . ?
C13 C8 C7 121.2(2) . . ?
C8 C9 C10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 O1 116.1(2) . . ?
C10 C11 O1 123.8(2) . . ?
O2 C12 C11 116.0(4) . . ?
O2 C12 C13 124.0(4) . . ?
C11 C12 C13 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12' O2' C15' 116.5(12) . . ?
N1 C1' C2' 122.8(13) . . ?
C1' C2' C3' 118.7(10) . . ?
C2' C3' C4' 118.0(10) . . ?
C2' C3' C6' 123.5(9) . . ?
C4' C3' C6' 118.5(10) . . ?
C5' C4' C3' 120.3(15) . . ?
N1 C5' C4' 121.5(17) . . ?
C3' C6' C7' 117.7(6) . . ?
C3' C6' C7' 117.5(6) . 2_666 ?
C7' C6' C7' 88.9(5) . 2_666 ?
C8' C7' C6' 120.5(6) . . ?
C8' C7' C6' 117.6(5) . 2_666 ?
C6' C7' C6' 91.1(5) . 2_666 ?
C9' C8' C13' 120.0 . . ?
C9' C8' C7' 124.5(5) . . ?
C13' C8' C7' 115.5(5) . . ?
C8' C9' C10' 120.0 . . ?
C11' C10' C9' 120.0 . . ?
O1 C11' C12' 116.2(5) . . ?
O1 C11' C10' 123.7(5) . . ?
C12' C11' C10' 120.0 . . ?
O2' C12' C11' 114.6(10) . . ?
O2' C12' C13' 125.4(10) . . ?
C11' C12' C13' 120.0 . . ?
C12' C13' C8' 120.0 . . ?
O2P N1P O3P 124.00(17) . . ?
O2P N1P C2P 118.70(16) . . ?
O3P N1P C2P 117.29(16) . . ?
O4P N2P O5P 123.55(17) . . ?
O4P N2P C4P 118.47(16) . . ?
O5P N2P C4P 117.98(17) . . ?
O7P N3P O6P 122.01(17) . . ?
O7P N3P C6P 119.61(17) . . ?
O6P N3P C6P 118.36(17) . . ?
O1P C1P C2P 122.51(18) . . ?
O1P C1P C6P 125.69(18) . . ?
C2P C1P C6P 111.69(17) . . ?
C3P C2P C1P 125.57(17) . . ?
C3P C2P N1P 116.46(17) . . ?
C1P C2P N1P 117.92(17) . . ?
C2P C3P C4P 118.29(18) . . ?
C5P C4P C3P 121.20(18) . . ?
C5P C4P N2P 119.48(17) . . ?
C3P C4P N2P 119.32(17) . . ?
C4P C5P C6P 119.62(18) . . ?
C5P C6P N3P 116.32(17) . . ?
C5P C6P C1P 123.56(17) . . ?
N3P C6P C1P 120.11(17) . . ?
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
O1 C11' 1.357(5) . ?
O1 C11 1.392(2) . ?
O1 C14 1.431(3) . ?
N1 C5 1.328(6) . ?
N1 C5' 1.334(14) . ?
N1 C1 1.341(6) . ?
N1 C1' 1.348(13) . ?
O2 C12 1.389(6) . ?
O2 C15 1.414(9) . ?
C1 C2 1.359(6) . ?
C2 C3 1.395(5) . ?
C3 C4 1.386(5) . ?
C3 C6 1.497(5) . ?
C4 C5 1.387(7) . ?
C6 C7 1.552(4) . ?
C6 C7 1.587(4) 2_666 ?
C7 C8 1.520(3) . ?
C7 C6 1.587(4) 2_666 ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 C10 1.3900 . ?
C10 C11 1.3900 . ?
C11 C12 1.3900 . ?
C12 C13 1.3900 . ?
O2' C12' 1.336(15) . ?
O2' C15' 1.48(2) . ?
C1' C2' 1.363(13) . ?
C2' C3' 1.376(10) . ?
C3' C4' 1.384(10) . ?
C3' C6' 1.498(11) . ?
C4' C5' 1.356(14) . ?
C6' C7' 1.543(9) . ?
C6' C7' 1.592(9) 2_666 ?
C7' C8' 1.523(8) . ?
C7' C6' 1.592(9) 2_666 ?
C8' C9' 1.3900 . ?
C8' C13' 1.3900 . ?
C9' C10' 1.3900 . ?
C10' C11' 1.3900 . ?
C11' C12' 1.3900 . ?
C12' C13' 1.3900 . ?
O1P C1P 1.256(2) . ?
O2P N1P 1.223(2) . ?
O3P N1P 1.225(2) . ?
O4P N2P 1.228(2) . ?
O5P N2P 1.233(2) . ?
O6P N3P 1.237(2) . ?
O7P N3P 1.230(2) . ?
N1P C2P 1.467(2) . ?
N2P C4P 1.450(3) . ?
N3P C6P 1.448(2) . ?
C1P C2P 1.442(3) . ?
C1P C6P 1.449(3) . ?
C2P C3P 1.357(3) . ?
C3P C4P 1.395(3) . ?
C4P C5P 1.375(3) . ?
C5P C6P 1.377(3) . ?
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
N1 H1 O1P 0.90(3) 1.74(3) 2.611(2) 164(3) 1_445
N1 H1 O7P 0.90(3) 2.46(3) 2.972(2) 117(2) 1_445
