An Unexpected Coupling-Reduction Tandem Reaction for Synthesis of Alkenyl-Substituted BODIPYs
Teng, Kun-Xu; Niu, Li-Ya; Li, Jie; Jia, Lu; Yang, Qing-Zheng; Chemical Communications  (2019) –; doi:10.1039/C9CC07730H

data_7124364
_publ_section_title
;
 An Unexpected Coupling-Reduction Tandem Reaction for Synthesis of
 Alkenyl-Substituted BODIPYs
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07730H
_journal_year                    2019
_chemical_formula_moiety         'C24 H19 B F2 N2'
_chemical_formula_sum            'C24 H19 B F2 N2'
_chemical_formula_weight         384.22
_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
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc23k12t
_audit_creation_date             2019-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2019-09-11 deposited with the CCDC.    2019-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                68.11(3)
_cell_angle_beta                 84.51(3)
_cell_angle_gamma                62.63(3)
_cell_formula_units_Z            4
_cell_length_a                   12.326(3)
_cell_length_b                   12.494(3)
_cell_length_c                   15.298(3)
_cell_measurement_reflns_used    5640
_cell_measurement_temperature    163(2)
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      1.4406
_cell_volume                     1933.1(11)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      163.15
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0838
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14856
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.966
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         6723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0904
_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^)+(0.0302P)^2^+2.0020P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5073
_reflns_number_total             6723
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07730h2.cif
_cod_data_source_block           bww19248
_cod_original_cell_volume        1933.2(9)
_cod_database_code               7124364
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.984
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11),
 C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34),
 C35(H35), C39(H39), C40(H40), C41(H41), C43(H43), C44(H44), C46(H46), C47(H47)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              75285
_olex2_submission_special_instructions 'No special instructions were received'