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_7242159
_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         'F6 P, C13 H12 N, C13 H11 N'
_chemical_formula_sum            'C26 H23 F6 N2 P'
_chemical_formula_weight         508.43
_chemical_name_systematic        'trans-4-stilbazole hexafluorophosphate'
_chemical_properties_physical    Light-sensitive
_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     dual
_audit_creation_date             2020-12-28
_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                84.721(5)
_cell_angle_beta                 76.416(5)
_cell_angle_gamma                70.095(2)
_cell_formula_units_Z            2
_cell_length_a                   10.6906(11)
_cell_length_b                   11.0302(11)
_cell_length_c                   11.0850(11)
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.34
_cell_volume                     1194.6(2)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      125.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.479
_diffrn_reflns_theta_min         1.890
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0503 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.9400.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       prism
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4886
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0488
_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^)+(0.0441P)^2^+0.7915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1230
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3635
_reflns_number_total             4886
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01885f2.cif
_cod_data_source_block           mcg1930_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7242157--7242159.cif.'
_cod_database_code               7242159
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C21-C20 \\sim C21-C20A
 with sigma of 0.02
 C16-C19 \\sim C16-C19A
 with sigma of 0.02
 C20-C19 \\sim C20A-C19A
 with sigma of 0.02
 C21-C19 \\sim C21-C19A
 with sigma of 0.04
 C16-C20 \\sim C16-C20A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C20A) = Uanis(C20)
Uanis(C19) = Uanis(C19A)
4. Others
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=1-FVAR(1)
 Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C8(H8), C11(H11), C7(H7), C13(H13), C5(H5), C2(H2),
 C12(H12), C1(H1A), C24(H24), C18(H18), C6(H6), C14(H14), C17(H17), C23(H23),
 C15(H15), C22(H22), C25(H25), C26(H26), C20(H20), C19(H19), C19A(H19A),
 C20A(H20A)
;
_shelx_res_checksum              84816
_olex2_submission_special_instructions 'No special instructions were received'