Photoreactive salt cocrystal: N±-H⋯N hydrogen bond and cation–π interactions support a cascade-like photodimerization of a 4-stilbazole
Li, Changan; Campillo-Alvarado, Gonzalo; Swenson, Dale C.; MacGillivray, Leonard R.; CrystEngComm 23 (2021) 1071–1074; doi:10.1039/D0CE01885F

data_7242158
_publ_section_title
;
 Photoreactive salt cocrystal: N+--H&#x22EF;N hydrogen bond and cation--\p
 interactions support a cascade-like photodimerization of a 4-stilbazole
;
_journal_issue                   5
_journal_name_full               CrystEngComm
_journal_page_first              1071
_journal_page_last               1074
_journal_paper_doi               10.1039/D0CE01885F
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C13 H11 N, C13 H12 N, F6 P'
_chemical_formula_sum            'C26 H23 F6 N2 P'
_chemical_formula_weight         508.43
_chemical_name_systematic
'trans-4-stilbazole, 1,3-bis(4'-pyridyl)-2,4-bis(phenyl)cyclobutane hexafluorophosphate'
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-29 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                87.742(10)
_cell_angle_beta                 83.324(9)
_cell_angle_gamma                65.023(9)
_cell_formula_units_Z            2
_cell_length_a                   9.930(7)
_cell_length_b                   11.296(8)
_cell_length_c                   11.859(9)
_cell_measurement_reflns_used    1786
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      20.27
_cell_measurement_theta_min      2.308
_cell_volume                     1197.6(15)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_av_unetI/netI     0.1564
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10862
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        23.499
_diffrn_reflns_theta_max         23.499
_diffrn_reflns_theta_min         1.729
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7269
_exptl_absorpt_correction_T_min  0.5899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0958 before and 0.0805 after correction.
The Ratio of minimum to maximum transmission is 0.8115.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       irregular
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3517
_refine_ls_number_restraints     99
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.2288
_refine_ls_R_factor_gt           0.1069
_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/[\s^2^(Fo^2^)+(0.1556P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2422
_refine_ls_wR_factor_ref         0.2896
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1448
_reflns_number_total             3517
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01885f2.cif
_cod_data_source_block           mcg1975
_cod_depositor_comments
'Adding full bibliography for 7242157--7242159.cif.'
_cod_database_code               7242158
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 F11A, F12A, P2A, F10A, F8A, F9A, F7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 H1, N1, H14, C14, H18, C18, H17, C17, C16, C15, H15
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C20(H20), C19(H19)
3.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C25(H25), C1(H1A), C9(H9), C7(H7), C2(H2), C17(H17), C22(H22),
 C4(H4), C6(H6), C24(H24), C5(H5), C23(H23), C13(H13), C10(H10), C15(H15),
 C18(H18), C11(H11), C14(H14), C12(H12)
;
_shelx_res_checksum              53436
_olex2_submission_special_instructions 'No special instructions were received'