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_7122818
_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         'C27 H35 B F2 N2 S3'
_chemical_formula_sum            'C27 H35 B F2 N2 S3'
_chemical_formula_weight         532.56
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-08-05
_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                90
_cell_angle_beta                 99.898(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2704(8)
_cell_length_b                   15.2656(10)
_cell_length_c                   15.5063(11)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      2.982
_cell_volume                     2861.3(3)
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            44815
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         2.982
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1112 before and 0.0745 after correction. The Ratio of minimum to maximum transmission is 0.8082. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0812
_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^)+(0.0775P)^2^+4.0703P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1868
_refine_ls_wR_factor_ref         0.2170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4414
_reflns_number_total             6368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09821b2.cif
_cod_data_source_block           mo_20180805b_0m
_cod_database_code               7122818
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C26A = C26-C25 = C27-C26 = C27A-C26A
 1.54 with sigma of 0.005
 C25-C27 = C25-C27A
 2.52 with sigma of 0.005
 S3-C9 \\sim S3A-C9
 with sigma of 0.02
 S3-C25 \\sim S3A-C25
 with sigma of 0.02
 C11A-C10 \\sim C11-C10 \\sim C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 F1-B1 \\sim F1A-B1 \\sim F2-B1 \\sim F2A-B1
 with sigma of 0.02
 F1-F2 \\sim F1A-F2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12A) = Uanis(C12)
Uanis(C11A) = Uanis(C11)
Uanis(C27) = Uanis(C27A)
4. Others
 Sof(H10C)=Sof(H10D)=Sof(H25C)=Sof(H25D)=Sof(S3A)=Sof(C26A)=Sof(H26C)=
 Sof(H26D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(F2)=Sof(C27)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(F1A)=1-FVAR(1)
 Sof(S3)=Sof(F1)=Sof(F2A)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=
 Sof(H26B)=Sof(C27A)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,
 H14B), C25(H25A,H25B), C25(H25C,H25D), C26(H26A,H26B), C26A(H26C,H26D),
 C11A(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C18(H18), C20(H20)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C27A(H27A,H27B,H27C), C12A(H12D,H12E,H12F),
 C27(H27D,H27E,H27F)
;
_shelx_res_checksum              69064
_olex2_submission_special_instructions 'No special instructions were received'