Pictet–Spengler Synthesis of Twist Quinoline-Fused BODIPYs as Heavy-Atom-Free Photosensitizers
Li, Wanwan; Gong, Qingbao; Wu, Qinghua; Guo, Luying; Guo, Xing; Guo, Dianjun; Jiao, Lijuan; Hao, Erhong; Chemical Communications  (2023) –; doi:10.1039/D3CC04460B

data_7132147
_publ_section_title
;
 Pictet--Spengler Synthesis of Twist Quinoline-Fused BODIPYs as
 Heavy-Atom-Free Photosensitizers
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04460B
_journal_year                    2023
_chemical_formula_moiety         'C30 H23 B F2 N4'
_chemical_formula_sum            'C30 H23 B F2 N4'
_chemical_formula_weight         488.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-15 deposited with the CCDC.	2023-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.146(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.348(4)
_cell_length_b                   18.253(6)
_cell_length_c                   11.465(4)
_cell_measurement_reflns_used    556
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      24.862
_cell_measurement_theta_min      2.371
_cell_volume                     2426.0(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker SMART APEX II diffractometer'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17303
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.201
_diffrn_reflns_theta_max         25.201
_diffrn_reflns_theta_min         2.081
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1745 before and 0.0637 after correction.
The Ratio of minimum to maximum transmission is 0.6963.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         4347
_refine_ls_number_restraints     236
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0952
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0676P)^2^+0.2520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1389
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2751
_reflns_number_total             4347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04460b2.cif
_cod_data_source_block           3c
_cod_original_cell_volume        2425.9(14)
_cod_database_code               7132147
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N4A-C17 \\sim N4-C17
 with sigma of 0.02
 N4A-C21A \\sim N4-C21
 with sigma of 0.02
 C18-C17 \\sim C18A-C17
 with sigma of 0.02
3. Restrained planarity
 C21A, C17, C18A, C20A, N4A, C19A
 with sigma of 0.1
 C21, C17, C18, C20, N4, C19
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
N4 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim N4A \\sim C18A \\sim
C19A \\sim C20A \\sim C21A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 N4, C17, C18, C19, C20, C21, N4A, C18A, C19A, C20A, C21A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
6. Same fragment restrains
{C18A, C19A, C20A, C21A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{C18, C19, C20, C21}
7. Others
 Sof(N4A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=
 Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(N4)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=
 Sof(H21)=FVAR(1)
8.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C26(H26), C18A(H18A),
 C19A(H19A), C20A(H20A), C21A(H21A)
8.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              94172
_olex2_submission_special_instructions 'No special instructions were received'