Synthesis and Spectroscopic and Cellular Properties of Near-IR [a]Phenanthrene-Fused 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes.
Zhao, Ning; Xuan, Sunting; Zhou, Zehua; Fronczek, Frank R.; Smith, Kevin M.; Vicente, M Graça H; The Journal of organic chemistry 82 (2017) 9744–9750; doi:10.1021/acs.joc.7b01940

data_4032772
_publ_section_title
;
 Synthesis and Spectroscopic and Cellular Properties of Near-IR
 [a]Phenanthrene-Fused 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9744
_journal_page_last               9750
_journal_paper_doi               10.1021/acs.joc.7b01940
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C51 H31 B F2 N2, 2(C H Cl3)'
_chemical_formula_sum            'C53 H33 B Cl6 F2 N2'
_chemical_formula_weight         959.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 103.7927(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.2486(5)
_cell_length_b                   9.3345(2)
_cell_length_c                   35.1839(9)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      32.86
_cell_measurement_theta_min      2.63
_cell_volume                     9010.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            78841
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         35.643
_diffrn_reflns_theta_min         1.485
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       needle
_exptl_crystal_F_000             3920
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.355
_refine_diff_density_min         -1.228
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         20739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0593P)^2^+8.3258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1435
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12940
_reflns_number_total             20739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01940_si_001.cif
_cod_data_source_block           NZhao87
_cod_depositor_comments          'Adding full bibliography for 4032772.cif.'
_cod_database_code               4032772
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.860
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              26797
_shelx_hkl_checksum              88938