Transition-Metal-Free Regioselective Cross-Coupling of BODIPYs with Thiols
Lv, Fan; Tang, Bing; Hao, Erhong; Liu, Qingyun; Wang, Hua; Jiao, Lijuan; Chemical Communications  (2019) –; doi:10.1039/C8CC09821B

data_7122817
_publ_section_title
;
 Transition-Metal-Free Regioselective Cross-Coupling of BODIPYs with
 Thiols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09821B
_journal_year                    2019
_chemical_formula_moiety         'C32 H29 B F2 N2 S2'
_chemical_formula_sum            'C32 H29 B F2 N2 S2'
_chemical_formula_weight         554.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-06 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                102.951(2)
_cell_angle_beta                 90.009(2)
_cell_angle_gamma                98.8670(10)
_cell_formula_units_Z            2
_cell_length_a                   7.8488(3)
_cell_length_b                   12.9762(5)
_cell_length_c                   17.3391(7)
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.549
_cell_measurement_theta_min      3.001
_cell_volume                     1699.35(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_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            86806
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         3.617
_exptl_absorpt_coefficient_mu    0.188
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         7539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.5761P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1395
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5482
_reflns_number_total             7539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09821b2.cif
_cod_data_source_block           20180614b
_cod_database_code               7122817
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.946
_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. Others
 Sof(S1A)=Sof(S2A)=Sof(F1A)=Sof(F2A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-
 FVAR(1)
 Sof(S1)=Sof(S2)=Sof(F1)=Sof(F2)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C19(H19), C21(H21), C27(H27), C28(H28), C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C32(H32A,H32B,
 H32C), C23(H23A,H23B,H23C), C23A(H23D,H23E,H23F)
;
_shelx_res_checksum              69720
_shelx_fab_checksum              375
_olex2_submission_special_instructions 'No special instructions were received'