Photosalient effect and photodimerization of mono- and dicationic organic salts incorporated in 4-styrylpyridine
Kusumoto, Sotaro; Wakabayashi, Kaede; Rakumitsu, Kenta; Kim, Yang; Koide, Yoshihiro; CrystEngComm 26 (2024) 3791–3794; doi:10.1039/D4CE00538D

data_7248927
_publ_section_title
;
 Photosalient effect and photodimerization of mono- and dicationic organic
 salts incorporated in 4-styrylpyridine
;
_journal_issue                   28
_journal_name_full               CrystEngComm
_journal_page_first              3791
_journal_page_last               3794
_journal_paper_doi               10.1039/D4CE00538D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '4(Br), 2(C38 H38 N2), 3(H2 O)'
_chemical_formula_sum            'C76 H82 Br4 N4 O3'
_chemical_formula_weight         1419.09
_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             2024-06-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-14 deposited with the CCDC.	2024-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                68.905(6)
_cell_angle_beta                 71.723(6)
_cell_angle_gamma                89.945(3)
_cell_formula_units_Z            2
_cell_length_a                   12.2770(5)
_cell_length_b                   16.0596(7)
_cell_length_c                   18.7305(15)
_cell_measurement_reflns_used    5914
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.1850
_cell_measurement_theta_min      2.0380
_cell_volume                     3245.5(4)
_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      120.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.785
_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    5.00    --  -10.00  45.00   0.00  360
  2  \w   -100.00 -10.00   0.50    5.00    --  -10.00  45.00  90.00  180
;
_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  0.0636
_diffrn_reflns_av_unetI/netI     0.1431
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.785
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23804
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.604
_diffrn_reflns_theta_min         1.761
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75114
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       block
_exptl_crystal_F_000             1460
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.483
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     791
_refine_ls_number_reflns         13059
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1732
_refine_ls_R_factor_gt           0.0939
_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^)+(0.0792P)^2^+15.1598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2020
_refine_ls_wR_factor_ref         0.2410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7100
_reflns_number_total             13059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00538d4.cif
_cod_data_source_block           230418_14benz_nore_autored
_cod_depositor_comments
'Adding full bibliography for 7248924--7248927.cif.'
_cod_database_code               7248927
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.884
_shelx_estimated_absorpt_t_min   0.786
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 H3B-Br1A
 2.1 with sigma of 0.01
 Br4A_$1-H1B
 2.23 with sigma of 0.01
 H47B-H65A
 2.1 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Br3A \\sim Br1 \\sim Br1A \\sim Br2A \\sim Br2 \\sim Br4A \\sim Br4: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
O1 \\sim O3 \\sim O2: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
Uanis(C72) \\sim Ueq, Uanis(C74) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C68) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C74) \\sim Ueq, Uanis(C75)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C45) \\sim Ueq, Uanis(C40) \\sim Ueq, Uanis(C41) \\sim Ueq, Uanis(C42)
\\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C44) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(C4) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C4) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C11) \\sim
Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C72) = Uanis(C74)
Uanis(C68) = Uanis(C72) = Uanis(C74) = Uanis(C75)
Uanis(C40) = Uanis(C41) = Uanis(C42) = Uanis(C45) = Uanis(C44) = Uanis(C43)
Uanis(C4) = Uanis(C9) = Uanis(C10) = Uanis(C11)
Uanis(C4) = Uanis(C7) = Uanis(C8) = Uanis(C11)
4. Rigid body (RIGU) restrains
 Br3A, Br1, Br1A, Br2A, Br2, Br4A, Br4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
 O1, O3, O2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C74)=Sof(H74)=Sof(C72)=Sof(H72)=1-FVAR(1)
 Sof(C73)=Sof(H73)=Sof(C71)=Sof(H71)=FVAR(1)
 Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=1-FVAR(2)
 Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=FVAR(2)
 Sof(Br2A)=1-FVAR(3)
 Sof(Br2)=FVAR(3)
 Sof(Br1A)=1-FVAR(4)
 Sof(Br1)=FVAR(4)
 Sof(Br4A)=1-FVAR(5)
 Sof(Br4)=FVAR(5)
6.a Free rotating group:
 O1(H1A,H1B), O2(H2A,H2B), O3(H3A,H3B)
6.b Ternary CH refined with riding coordinates:
 C73(H73), C71(H71), C9(H9), C10(H10)
6.c Secondary CH2 refined with riding coordinates:
 C50(H50A,H50B), C51(H51A,H51B), C16(H16A,H16B), C65(H65A,H65B)
6.d Aromatic/amide H refined with riding coordinates:
 C57(H57), C70(H70), C55(H55), C32(H32), C39(H39), C52(H52), C27(H27),
 C31(H31), C66(H66), C62(H62), C61(H61), C38(H38), C29(H29), C28(H28), C64(H64),
  C35(H35), C63(H63), C14(H14), C56(H56), C53(H53), C58(H58), C33(H33),
 C37(H37), C60(H60), C13(H13), C69(H69), C36(H36), C5(H5), C15(H15), C3(H3),
 C80(H80), C2(H2), C76(H76), C67(H67), C12(H12), C79(H79), C1(H1), C77(H77),
 C6(H6), C78(H78), C74(H74), C72(H72), C7(H7), C8(H8)
6.e Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C49(H49A,H49B,H49C), C24(H24A,H24B,H24C), C23(H23A,H23B,
 H23C), C48(H48A,H48B,H48C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C26(H26A,
 H26B,H26C)
;
_shelx_res_checksum              57415
_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
;