Development of a Class of Easily Scalable, Electron-Deficient, Core-Extended Benzo-Fused Azadipyrromethene Derivatives ("MB-DIPY").
Zatsikha, Yuriy V.; Shamova, Liliya I.; Blesener, Tanner S.; Kuzmin, Ilya A.; Germanov, Yaroslaw V.; Herbert, David E.; Nemykin, Victor N.; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02074

data_4033644
_publ_section_title
;
 Development of a Class of Easily Scalable, Electron-Deficient,
 Core-Extended Benzo-Fused Azadipyrromethene Derivatives
 (&quot;MB-DIPY&quot;).
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02074
_journal_year                    2019
_chemical_formula_sum            'C17 H12 B F2 N O3'
_chemical_formula_weight         327.09
_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
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                83.268(9)
_cell_angle_beta                 76.710(9)
_cell_angle_gamma                85.528(9)
_cell_formula_units_Z            4
_cell_length_a                   7.3366(19)
_cell_length_b                   14.047(4)
_cell_length_c                   14.462(4)
_cell_measurement_reflns_used    1756
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.98
_cell_measurement_theta_min      2.86
_cell_volume                     1438.5(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO CMOS'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved--crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1312
_diffrn_reflns_av_unetI/netI     0.1432
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15437
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        24.882
_diffrn_reflns_theta_max         24.882
_diffrn_reflns_theta_min         2.857
_diffrn_source                   'fine-focus tube'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.546
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         4921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.546
_refine_ls_R_factor_all          0.1836
_refine_ls_R_factor_gt           0.1067
_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^)+(0.0237P)^2^+4.2466P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2231
_refine_ls_wR_factor_ref         0.2420
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             4921
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02074_si_002.cif
_cod_data_source_block           7b
_cod_original_cell_volume        1438.4(6)
_cod_database_code               4033644
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.988
_shelx_estimated_absorpt_t_max   0.994
_shelx_res_checksum              31868
_shelx_hkl_checksum              82052