Highly regioselective palladium-catalyzed domino reaction for post-functionalization of BODIPY.
Wang, Sisi; Wang, Zhaoli; Gao, Hu; Jiang, Liang; Liu, Hui; Wu, Fan; Zhao, Yue; Chan, Kin Shing; Shen, Zhen; Chemical communications (Cambridge, England) 57 (2021) 1758–1761; doi:10.1039/d0cc08163a

data_7127769
_publ_section_title
;
 Highly regioselective palladium-catalyzed domino reaction for
 post-functionalization of BODIPY.
;
_journal_issue                   14
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1758
_journal_page_last               1761
_journal_paper_doi               10.1039/d0cc08163a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '2(C68 H71 B F2 N2)'
_chemical_formula_sum            'C136 H142 B2 F4 N4'
_chemical_formula_weight         1930.15
_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             2019-11-17
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-11-27 deposited with the CCDC.	2021-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.149(2)
_cell_angle_beta                 91.366(2)
_cell_angle_gamma                90.205(2)
_cell_formula_units_Z            2
_cell_length_a                   15.7803(6)
_cell_length_b                   16.9989(6)
_cell_length_c                   21.4911(8)
_cell_measurement_reflns_used    9746
_cell_measurement_temperature    189.99
_cell_measurement_theta_max      52.82
_cell_measurement_theta_min      2.89
_cell_volume                     5763.2(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      189.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  "'Bruker d8 venture"
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            62166
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        51.248
_diffrn_reflns_theta_max         51.248
_diffrn_reflns_theta_min         2.261
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.5582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1531 before and 0.0889 after correction. The Ratio of minimum to maximum transmission is 0.7438. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       block
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1506
_refine_ls_number_reflns         18381
_refine_ls_number_restraints     444
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0732
_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^)+(0.1325P)^2^+1.6180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13040
_reflns_number_total             18381
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08163a2.cif
_cod_data_source_block           20191031zh_shenzhen_wss817_0m_a
_cod_depositor_comments
'Adding full bibliography for 7127767--7127769.cif.'
_cod_database_code               7127769
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8690(11)
 0.1310(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C10-C02V
 1.5 with sigma of 0.02
 C8-C10
 1.5 with sigma of 0.02
 C7-C10
 1.5 with sigma of 0.02
 C18-C035
 1.5 with sigma of 0.02
 C18-C03T
 1.5 with sigma of 0.02
 C19-C18
 1.5 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
C4 \\sim C6 \\sim C5 \\sim C3 \\sim C1 \\sim C2 \\sim C03H: within 1.7A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
C03O \\sim C03W \\sim C03Y \\sim C03Z \\sim C8 \\sim C7 \\sim C10 \\sim C14:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
C11 \\sim C02W \\sim C12 \\sim C13 \\sim C9 \\sim C02M \\sim C02P \\sim C022
\\sim C00I \\sim C00R: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.7A
C014 \\sim C01O \\sim C02F \\sim C02G \\sim C02S \\sim C037 \\sim C15 \\sim C16
\\sim C17 \\sim C20: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 1.7A
C03K \\sim C03T \\sim C03V \\sim C03X \\sim C18 \\sim C21 \\sim C19 \\sim C24:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 1.7A
5. Others
 Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(H4C)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=Sof(C6)=
 Sof(H6A)=Sof(H6B)=Sof(H6C)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(1)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=
 Sof(C10)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=1-FVAR(2)
 Sof(C03O)=Sof(C03W)=Sof(H10)=Sof(HR)=Sof(HS)=Sof(C03Y)=Sof(H11)=Sof(HV)=
 Sof(HW)=Sof(C03Z)=Sof(H12)=Sof(HX)=Sof(HY)=FVAR(2)
 Sof(C9)=Sof(H9A)=Sof(C11)=Sof(H11A)=Sof(C12)=Sof(H12A)=Sof(C13)=Sof(H13)=1-
 FVAR(3)
 Sof(C022)=Sof(H022)=Sof(C02M)=Sof(H02T)=Sof(C02P)=Sof(H02Z)=Sof(C02W)=Sof(H1)=
 FVAR(3)
 Sof(C16)=Sof(H16)=Sof(C15)=Sof(H15)=Sof(C20)=Sof(H20)=Sof(C17)=Sof(H17)=1-
 FVAR(4)
 Sof(C02F)=Sof(H02F)=Sof(C02G)=Sof(H02G)=Sof(C02S)=Sof(H02S)=Sof(C037)=
 Sof(H037)=FVAR(4)
 Sof(C18)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C19)=Sof(H19A)=Sof(H19B)=
 Sof(H19C)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=1-FVAR(5)
 Sof(C03K)=Sof(C03T)=Sof(H03S)=Sof(H03T)=Sof(H03U)=Sof(C03V)=Sof(H03V)=
 Sof(H03W)=Sof(H03X)=Sof(C03X)=Sof(H03Y)=Sof(HT)=Sof(HU)=FVAR(5)
6.a Riding coordinates:
 C7(H7A,H7B,H7C)
6.b Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00E(H00E), C00H(H00H), C00M(H00M), C00X(H00X), C00Z(H00Z),
 C016(H016), C019(H019), C01D(H01D), C01F(H01H), C01G(H01I), C01I(H01J),
 C01L(H01L), C01P(H01P), C01W(H01W), C01Z(H01Z), C020(H020), C021(H021),
 C022(H022), C023(H023), C025(H025), C026(H026), C027(H027), C028(H028),
 C029(H029), C02A(H02A), C02B(H02B), C02C(H02C), C02E(H02E), C02F(H02F),
 C02G(H02G), C02H(H02P), C02I(H02Q), C02J(H02J), C02K(H02R), C02L(H02L),
 C02M(H02T), C02N(H02N), C02P(H02Z), C02Q(H02), C02S(H02S), C02W(H1),
 C02X(H02X), C02Y(H02Y), C030(H030), C031(H031), C032(H032), C033(H033),
 C034(H034), C037(H037), C039(H039), C03B(H03Z), C9(H9A), C11(H11A), C12(H12A),
 C13(H13), C16(H16), C15(H15), C20(H20), C17(H17)
6.c Fitted hexagon refined as free rotating group:
 C9(C11,C00R,C12,C13,C00I), C16(C15,C014,C20,C17,C01O)
6.d Idealised Me refined as rotating group:
 C01S(H01A,H01B,H01C), C01X(H01E,H01F,H01G), C01Y(H01K,H01M,H01N), C024(H02K,
 H02M,H02O), C02O(H02U,H02V,H02W), C02R(H02D,H02H,H02I), C036(H03A,H03B,H03C),
 C03D(H03D,H03E,H03F), C03E(H03,H,HA), C03F(H2,HB,HC), C03G(H3,HD,HE),
 C03I(H03G,H03H,H03I), C03J(H03J,H03K,H03L), C03L(H4,HF,HG), C03M(H03M,H03N,
 H03O), C03N(H5,HH,HI), C03P(H6,HJ,HK), C03Q(H03P,H03Q,H03R), C03R(H7,HL,HM),
 C03S(H8,HN,HO), C03T(H03S,H03T,H03U), C03U(H9,HP,HQ), C03V(H03V,H03W,H03X),
 C03W(H10,HR,HS), C03X(H03Y,HT,HU), C03Y(H11,HV,HW), C03Z(H12,HX,HY), C1(H1A,
 H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C),
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C14(H14A,H14B,H14C), C21(H21A,H21B,H21C),
 C19(H19A,H19B,H19C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              7203
_shelx_hkl_checksum              27381
_olex2_submission_special_instructions 'No special instructions were received'