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_7242157
_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, C4.59 H3.91 N0.51, C8.41 H7.09 N0.49, C9.58 H9.13 N0.84, C3.42 H2.87 N0.16'
_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
_audit_creation_date             2020-12-29
_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                84.292(5)
_cell_angle_beta                 75.957(5)
_cell_angle_gamma                69.533(5)
_cell_formula_units_Z            2
_cell_length_a                   10.8408(11)
_cell_length_b                   11.1512(11)
_cell_length_c                   11.3568(11)
_cell_measurement_reflns_used    3554
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.34
_cell_volume                     1247.6(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      298.15
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker Nonius APEX II Kappa'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5701
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        24.500
_diffrn_reflns_theta_max         24.500
_diffrn_reflns_theta_min         2.057
_exptl_absorpt_coefficient_mu    0.172
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_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          0.22
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.025
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0808P)^2^+0.1641P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2626
_reflns_number_total             3922
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01885f2.cif
_cod_data_source_block           mcg1930
_cod_depositor_comments
'Adding full bibliography for 7242157--7242159.cif.'
_cod_database_code               7242157
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C21-C20 \\sim C21-C20B
 with sigma of 0.02
 C16-C19 \\sim C16-C19B
 with sigma of 0.02
 C20-C19 \\sim C20B-C19B
 with sigma of 0.02
 C21-C19 \\sim C21-C19B
 with sigma of 0.04
 C16-C20 \\sim C16-C20B
 with sigma of 0.04
 P1-F3 \\sim P1-F4B
 with sigma of 0.02
 P1-F4 \\sim P1-F1B
 with sigma of 0.02
 P1-F6 \\sim P1-F3B
 with sigma of 0.02
 P1-F5 \\sim P1-F2B
 with sigma of 0.02
 C21-C26 \\sim C21B-C22B
 with sigma of 0.02
 C21-C22 \\sim C21B-C26B
 with sigma of 0.02
 C21-C20 \\sim C21B-C20
 with sigma of 0.02
 C21-C20B \\sim C21B-C20B
 with sigma of 0.02
 C24-C25 \\sim C24B-C23B
 with sigma of 0.02
 C24-C25B \\sim C24B-C25B
 with sigma of 0.02
 C26-C25 \\sim C22B-C23B
 with sigma of 0.02
 C22-C25B \\sim C26B-C25B
 with sigma of 0.02
 C21-C25 \\sim C21B-C23B
 with sigma of 0.04
 C21-C25B \\sim C21B-C25B
 with sigma of 0.04
 C24-C26 \\sim C24B-C22B
 with sigma of 0.04
 C26-C22 \\sim C22B-C26B
 with sigma of 0.04
 C26-C20 \\sim C22B-C20
 with sigma of 0.04
 C26-C20B \\sim C22B-C20B
 with sigma of 0.04
 C25-C25B \\sim C23B-C25B
 with sigma of 0.04
 C22-C20 \\sim C26B-C20
 with sigma of 0.04
 C22-C20B \\sim C26B-C20B
 with sigma of 0.04
 N1-C5 \\sim N1B-C5B
 with sigma of 0.02
 N1-C1 \\sim N1B-C1B
 with sigma of 0.02
 C5-C4 \\sim C5B-C4B
 with sigma of 0.02
 C1-C2 \\sim C1B-C2B
 with sigma of 0.02
 C2-C3 \\sim C2B-C3B
 with sigma of 0.02
 C4-C3 \\sim C4B-C3B
 with sigma of 0.02
 C3-C6 \\sim C3B-C6
 with sigma of 0.02
 C3-C6B \\sim C3B-C6B
 with sigma of 0.02
 N1-C2 \\sim N1B-C2B
 with sigma of 0.04
 N1-C4 \\sim N1B-C4B
 with sigma of 0.04
 C5-C1 \\sim C5B-C1B
 with sigma of 0.04
 C5-C3 \\sim C5B-C3B
 with sigma of 0.04
 C1-C3 \\sim C1B-C3B
 with sigma of 0.04
 C2-C4 \\sim C2B-C4B
 with sigma of 0.04
 C2-C6 \\sim C2B-C6
 with sigma of 0.04
 C2-C6B \\sim C2B-C6B
 with sigma of 0.04
 C4-C6 \\sim C4B-C6
 with sigma of 0.04
 C4-C6B \\sim C4B-C6B
 with sigma of 0.04
 C6B-C3B \\sim C6-C3
 with sigma of 0.02
 N2-C14 \\sim N2B-C18B
 with sigma of 0.02
 N2-C18 \\sim N2B-C14B
 with sigma of 0.02
 C14-C15 \\sim C18B-C17B
 with sigma of 0.02
 C18-C17 \\sim C14B-C15B
 with sigma of 0.02
 C15-C16 \\sim C17B-C16B
 with sigma of 0.02
 C16-C17 \\sim C16B-C15B
 with sigma of 0.02
 C16-C19 \\sim C16B-C19
 with sigma of 0.02
 C16-C19B \\sim C16B-C19B
 with sigma of 0.02
 N2-C15 \\sim N2B-C17B
 with sigma of 0.04
 N2-C17 \\sim N2B-C15B
 with sigma of 0.04
 C14-C18 \\sim C18B-C14B
 with sigma of 0.04
 C14-C16 \\sim C18B-C16B
 with sigma of 0.04
 C18-C16 \\sim C14B-C16B
 with sigma of 0.04
 C15-C17 \\sim C17B-C15B
 with sigma of 0.04
 C15-C19 \\sim C17B-C19
 with sigma of 0.04
 C15-C19B \\sim C17B-C19B
 with sigma of 0.04
 C17-C19 \\sim C15B-C19
 with sigma of 0.04
 C17-C19B \\sim C15B-C19B
 with sigma of 0.04
 C12-C13 \\sim C10B-C9B
 with sigma of 0.02
 C12-C11 \\sim C10B-C11B
 with sigma of 0.02
 C13-C8 \\sim C9B-C8B
 with sigma of 0.02
 C8-C9 \\sim C8B-C13B
 with sigma of 0.02
 C8-C7 \\sim C8B-C7
 with sigma of 0.02
 C8-C7B \\sim C8B-C7B
 with sigma of 0.02
 C9-C10 \\sim C13B-C12B
 with sigma of 0.02
 C10-C11 \\sim C12B-C11B
 with sigma of 0.02
 C12-C8 \\sim C10B-C8B
 with sigma of 0.04
 C12-C10 \\sim C10B-C12B
 with sigma of 0.04
 C13-C9 \\sim C9B-C13B
 with sigma of 0.04
 C13-C11 \\sim C9B-C11B
 with sigma of 0.04
 C13-C7 \\sim C9B-C7
 with sigma of 0.04
 C13-C7B \\sim C9B-C7B
 with sigma of 0.04
 C8-C10 \\sim C8B-C12B
 with sigma of 0.04
 C9-C11 \\sim C13B-C11B
 with sigma of 0.04
 C9-C7 \\sim C13B-C7
 with sigma of 0.04
 C9-C7B \\sim C13B-C7B
 with sigma of 0.04
 C7-C8 \\sim C7B-C8B
 with sigma of 0.02
3. Restrained planarity
 C3B, C2B, C1B, N1B, C5B, C4B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C7) = Uanis(C7B)
Uanis(C6B) = Uanis(C6)
Uanis(C21) = Uanis(C21B)
Uanis(C22) = Uanis(C26B)
Uanis(C22B) = Uanis(C26)
Uanis(C23B) = Uanis(C25)
Uanis(C24B) = Uanis(C24)
Uanis(C23) = Uanis(C25B)
Uanis(C3) = Uanis(C3B)
Uanis(C2) = Uanis(C2B)
Uanis(C1) = Uanis(C1B)
Uanis(N1) = Uanis(N1B)
Uanis(C5) = Uanis(C5B)
Uanis(C4) = Uanis(C4B)
Uanis(C16) = Uanis(C16B)
Uanis(C15B) = Uanis(C17)
Uanis(C18) = Uanis(C14B)
Uanis(N2) = Uanis(N2B)
Uanis(C14) = Uanis(C18B)
Uanis(C15) = Uanis(C17B)
Uanis(C8B) = Uanis(C8)
Uanis(C9B) = Uanis(C13)
Uanis(C10B) = Uanis(C12)
Uanis(C11B) = Uanis(C11)
Uanis(C12B) = Uanis(C10)
Uanis(C13B) = Uanis(C9)
5. Others
 Sof(C20B)=Sof(H20B)=Sof(C19B)=Sof(H19B)=1-FVAR(1)
 Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=FVAR(1)
 Sof(F4B)=Sof(F1B)=Sof(F3B)=Sof(F2B)=1-FVAR(2)
 Sof(F4)=Sof(F6)=Sof(F5)=Sof(F3)=FVAR(2)
 Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=1-FVAR(3)
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=FVAR(3)
 Sof(C21B)=Sof(C26B)=Sof(H26B)=Sof(C24B)=Sof(H24B)=Sof(C23B)=Sof(H23B)=
 Sof(C22B)=Sof(H22B)=1-FVAR(4)
 Sof(C21)=Sof(C22)=Sof(H22)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=Sof(C26)=
 Sof(H26)=FVAR(4)
 Sof(C25B)=Sof(H25B)=1-FVAR(5)
 Sof(C23)=Sof(H23)=FVAR(5)
 Sof(C3B)=Sof(C2B)=Sof(H2B)=Sof(C1B)=Sof(H1B)=Sof(N1B)=Sof(C5B)=Sof(H5B)=
 Sof(C4B)=Sof(H4B)=1-FVAR(6)
 Sof(N1)=Sof(C5)=Sof(H5)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(H2)=Sof(C4)=Sof(H4)=
 Sof(C3)=FVAR(6)
 Sof(C16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(N2B)=Sof(C14B)=
 Sof(H14B)=Sof(C15B)=Sof(H15B)=1-FVAR(7)
 Sof(N2)=Sof(C14)=Sof(H14)=Sof(C18)=Sof(H18)=Sof(C15)=Sof(H15)=Sof(C16)=
 Sof(C17)=Sof(H17)=FVAR(7)
 Sof(C8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=
 Sof(H12B)=Sof(C13B)=Sof(H13B)=1-FVAR(8)
 Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=
 Sof(C11)=Sof(H11)=FVAR(8)
6.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C14(H14), C18(H18),
 C15(H15), C17(H17), C25B(H25B), C20(H20), C19(H19), C20B(H20B), C19B(H19B),
 C5(H5), C1(H1A), C2(H2), C12(H12), C13(H13), C9(H9), C10(H10), C11(H11),
 C4(H4), C6(H6), C7(H7), C6B(H6B), C7B(H7B), C26B(H26B), C24B(H24B), C23B(H23B),
  C22B(H22B), C2B(H2B), C1B(H1B), C5B(H5B), C4B(H4B), C17B(H17B), C18B(H18B),
 C14B(H14B), C15B(H15B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B),
 C13B(H13B)
6.b Fitted hexagon refined as free rotating group:
 C21(C22,C23,C24,C25,C26), C12(C13,C8,C9,C10,C11)
;
_shelx_res_checksum              90874
_olex2_submission_special_instructions 'No special instructions were received'