Regioselective functionalization at the 7-position of 1,2,3-triphenylbenzo[b]phosphole oxide via P[double bond, length as m-dash]O-directed lithiation.
Wakatsuki, Ayana; Yukimoto, Mariko; Minoura, Mao; Fujii, Kaori; Kimura, Yoshifumi; Matano, Yoshihiro; Dalton transactions (Cambridge, England : 2003) 47 (2018) 7123–7127; doi:10.1039/c8dt01503a

data_7046231
_publ_section_title
;
 Regioselective functionalization at the 7-position of
 1,2,3-triphenylbenzo[b]phosphole oxide via P[double bond, length as
 m-dash]O-directed lithiation.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              7123
_journal_page_last               7127
_journal_paper_doi               10.1039/c8dt01503a
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         '(C70 H52 B F N2 O3 P2), 0.5(C4H10O), H2O'
_chemical_formula_sum            'C72 H59 B F N2 O4.5 P2'
_chemical_formula_weight         1115.96
_chemical_name_systematic        BODIPY_phosphole
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-29 deposited with the CCDC.
2018-05-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.421(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.9407(10)
_cell_length_b                   10.2627(4)
_cell_length_c                   32.0520(7)
_cell_measurement_reflns_used    39607
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      1.403
_cell_volume                     11787.2(6)
_computing_cell_refinement       'Rapid Auto'
_computing_data_collection       'Rapid Auto'
_computing_data_reduction        'Rapid Auto'
_computing_molecular_graphics
'Yadokari-XG 2011 (Wakita Nemoto et al. 2011)'
_computing_publication_material
'Yadokari-XG 2011 (Wakita Nemoto et al. 2011)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT-2013
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 14.629
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       \w
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.78228
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            39607
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.403
_diffrn_source                   'SPring-8 BL40XU'
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.7373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       plate
_exptl_crystal_F_000             4680
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane and diethyl ether'
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.124
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     762
_refine_ls_number_reflns         7698
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.175
_refine_ls_R_factor_all          0.0684
_refine_ls_R_factor_gt           0.0573
_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^)+(0.1041P)^2^+8.1075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1716
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6745
_reflns_number_total             7698
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt01503a2.cif
_cod_data_source_block           MM06MTN
_cod_depositor_comments
'Adding full bibliography for 7046230--7046231.cif.'
_cod_original_formula_sum        'C72 H59 B F N2 O4.50 P2'
_cod_database_code               7046231
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.997
_shelx_res_checksum              64501