Photosalient ionic cocrystal composed of trimesic acid and 4-styrylpyridine
Kusumoto, Sotaro; Sato, Kei; Muraie, Kouki; Masuda, Shunya; Rakumitsu, Kenta; Kim, Yang; Koide, Yoshihiro; CrystEngComm 25 (2023) 909–912; doi:10.1039/D2CE01592G

data_7246133
_publ_section_title
;
 Photosalient ionic cocrystal composed of trimesic acid and
 4-styrylpyridine
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              909
_journal_page_last               912
_journal_paper_doi               10.1039/D2CE01592G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C9 H5 O6, C13 H12 N, C13 H11 N'
_chemical_formula_sum            'C35 H28 N2 O6'
_chemical_formula_weight         572.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-12-15
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-12-25 deposited with the CCDC.	2023-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.343(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6213(5)
_cell_length_b                   36.7554(16)
_cell_length_c                   9.9466(6)
_cell_measurement_reflns_used    7322
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.0660
_cell_measurement_theta_min      2.2320
_cell_volume                     2893.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -100.00  80.00   0.50    8.00    --  -10.00  45.00   0.00  360
  2  \w   -100.00 -25.00   0.50    8.00    --  -10.00  45.00  90.00  150
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19065
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.216
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5744
_refine_ls_number_restraints     391
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0633
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0644P)^2^+0.8283P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1597
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4040
_reflns_number_total             5744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce01592g4.cif
_cod_data_source_block           221012_trimesin_4spy4_autored
_cod_depositor_comments          'Adding full bibliography for 7246133.cif.'
_cod_database_code               7246133
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C28-C25
 1.54 with sigma of 0.02
 C29-C30
 1.54 with sigma of 0.02
 C29A-C28A
 1.364 with sigma of 0.02
 C28A-C30A
 2.48 with sigma of 0.04
 C29A-C31A
 2.3 with sigma of 0.04
 C31A-C29A
 2.2 with sigma of 0.001
 C29A-C35A
 2.75 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
C30 \\sim C31 \\sim C35 \\sim C32 \\sim C33 \\sim C29 \\sim C34 \\sim C28 \\sim
C28A \\sim C29A \\sim C30A \\sim C35A \\sim C34A \\sim C33A \\sim C32A \\sim
C31A: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within
2A
Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(C30) = Uanis(C31) = Uanis(C32) = Uanis(C33) = Uanis(C34) = Uanis(C35)
4. Rigid body (RIGU) restrains
 C30, C31, C32, C33, C34, C35
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C30, C31, C35, C32, C33, C29, C34, C28, C28A, C29A, C30A, C35A, C34A, C33A,
 C32A, C31A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(C31A)=Sof(H31A)=
 Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=
 Sof(H35A)=1-FVAR(1)
 Sof(C30)=Sof(C35)=Sof(H35)=Sof(C34)=Sof(H34)=Sof(C33)=Sof(H33)=Sof(C32)=
 Sof(H32)=Sof(C31)=Sof(H31)=Sof(C29)=Sof(H29)=Sof(C28)=Sof(H28)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C6(H6), C4(H4), C15(H15), C16(H16), C14(H14), C13(H13),
 C35(H35), C34(H34), C33(H33), C32(H32), C31(H31), C11(H11), C10(H10), C22(H22),
  C27(H27), C18(H18), C20(H20), C23(H23), C26(H26), C19(H19), C24(H24),
 C21(H21), C29(H29), C28(H28), C28A(H28A), C29A(H29A), C31A(H31A), C32A(H32A),
 C33A(H33A), C34A(H34A), C35A(H35A)
6.b Fitted hexagon refined as free rotating group:
 C30(C35,C34,C33,C32,C31), C30A(C31A,C32A,C33A,C34A,C35A)
6.c Tetrahedral OH refined with riding coordinates:
 O5(H5)
6.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              53429
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;