Replacing the BO in BODIPY: unlocking the path to SBDIPY and BIDIPY chromophores.
Korzun, André; Crespi, Stefano; Golz, Christopher; Bismuto, Alessandro; Chemical science 14 (2023) 6579–6584; doi:10.1039/d3sc01493b

data_1569329
_publ_section_title
;
 Replacing the BO in BODIPY: unlocking the path to SBDIPY and BIDIPY
 chromophores.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              6579
_journal_page_last               6584
_journal_paper_doi               10.1039/d3sc01493b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C13 H15 Cl2 N2 Sb'
_chemical_formula_sum            'C13 H15 Cl2 N2 Sb'
_chemical_formula_weight         391.92
_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             2022-01-20
_audit_creation_method
;
FinalCif V96 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-02-13 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.646(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7292(5)
_cell_length_b                   9.9358(6)
_cell_length_c                   13.9550(7)
_cell_measurement_reflns_used    9706
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      35.333
_cell_measurement_theta_min      2.518
_cell_volume                     1487.03(14)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection
'Bruker BIS V6.2.15/2021-03-15 && APEX4 2021.4-0'
_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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Ag'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            67080
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         35.597
_diffrn_reflns_theta_min         1.899
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.199
_exptl_absorpt_correction_T_max  0.8773
_exptl_absorpt_correction_T_min  0.8028
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0639 before and 0.0382 after correction.
The Ratio of minimum to maximum transmission is 0.9151.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.751
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.111
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         6547
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0176
_refine_ls_R_factor_gt           0.0151
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0160P)^2^+0.6199P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0368
_refine_ls_wR_factor_ref         0.0379
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6127
_reflns_number_total             6547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01493b2.cif
_cod_data_source_block           mo_1555_cg_0m
_cod_database_code               1569329
_shelx_shelxl_version_number     2018/3
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C11-H11A \\sim C11-H11E
 with sigma of 0.02
 C11-H11C \\sim C11-H11D
 with sigma of 0.02
 C11-H11B \\sim C11-H11E
 with sigma of 0.02
3. Others
 Sof(H11D)=Sof(H11E)=Sof(H11F)=1-FVAR(1)
 Sof(H11A)=Sof(H11B)=Sof(H11C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C9(H9)
4.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C11(H11A,H11B,H11C), C11(H11D,H11E,H11F), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.735
_shelx_estimated_absorpt_t_max   0.792
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_shelx_res_checksum              40534