Exploring the π-System of the (Aza-)BOIMPY Scaffold: Electron-Rich Pyrrole Moieties Working in Concert with Electron-Depleted Meso-Positions.
Patalag, Lukas J.; Loch, Maximilian; Jones, Peter G.; Werz, Daniel B.; The Journal of organic chemistry 84 (2019) 7804–7814; doi:10.1021/acs.joc.9b00603

data_4034669
_publ_section_title
;
 Exploring the \p-System of the (Aza-)BOIMPY Scaffold: Electron-Rich
 Pyrrole Moieties Working in Concert with Electron-Depleted
 Meso-Positions.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7804
_journal_page_last               7814
_journal_paper_doi               10.1021/acs.joc.9b00603
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C34 H38 B2 F4 N6 O2'
_chemical_formula_weight         660.32
_space_group_crystal_system      monoclinic
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_space_group_name_Hall           'P 2yb'
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_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-02-28 deposited with the CCDC.	2019-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_measurement_temperature    100(2)
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_cell_volume                     6507.35(19)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
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_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL
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_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
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_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
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_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            267960
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         76.247
_diffrn_reflns_theta_min         3.176
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.836
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92308
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_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       tablet
_exptl_crystal_F_000             2768
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(6)
_refine_ls_extinction_coef       0.00041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1772
_refine_ls_number_reflns         26770
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0578P)^2^+0.9383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                25651
_reflns_number_total             26770
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00603_si_002.cif
_cod_data_source_block           patgold
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4034669
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.787
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              70546
_shelx_hkl_checksum              41168