Phenanthro[<i>b</i>]-Fused BODIPYs through Tandem Suzuki and Oxidative Aromatic Couplings: Synthesis and Photophysical Properties.
Miao, Wei; Feng, Yuanmei; Wu, Qinghua; Sheng, Wanle; Li, Mao; Liu, Qingyun; Hao, Erhong; Jiao, Lijuan; The Journal of organic chemistry 84 (2019) 9693–9704; doi:10.1021/acs.joc.9b01425

data_4034405
_publ_section_title
;
 Phenanthro[<i>b</i>]-Fused BODIPYs through Tandem Suzuki and Oxidative
 Aromatic Couplings: Synthesis and Photophysical Properties.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9693
_journal_page_last               9704
_journal_paper_doi               10.1021/acs.joc.9b01425
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         '0.04(C75 H65 B F2 N2)'
_chemical_formula_sum            'C75 H65 B F2 N2'
_chemical_formula_weight         1043.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-11-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4881(8)
_cell_length_b                   34.080(4)
_cell_length_c                   21.122(2)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.95
_cell_volume                     6829.9(12)
_computing_cell_refinement       '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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.1545
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            208828
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.596
_diffrn_reflns_theta_min         2.797
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1057 before and 0.0718 after correction.
The Ratio of minimum to maximum transmission is 0.9277.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic light red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_description       needle
_exptl_crystal_F_000             3539
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 1678 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         7866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0690
_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^)+(0.0883P)^2^+2.9553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1828
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                5025
_reflns_number_total             7866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01425_si_002.cif
_cod_data_source_block           a_sq
_cod_original_cell_volume        6829.9(11)
_cod_database_code               4034405
_shelx_shelxl_version_number     2014/7
_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
 Fixed Sof: C36(0.5) C40(0.5) C50(0.5) C2(0.5) C1AA(0.5) C0AA(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23),
 C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C33(H33), C35(H35)
3.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C34(H34A,H34B,H34C), C39(H39A,H39B,
 H39C), C41(H41A,H41B,H41C), C48(H48A,H48B,H48C)
;
_shelx_res_checksum              41110
_shelx_hkl_checksum              31919
_shelx_fab_checksum              84452
_olex2_submission_special_instructions 'No special instructions were received'