BODIPY analogues: synthesis and photophysical studies of difluoro boron complexes from 2-aminotropone scaffolds through N,O-chelation.
Palai, Bibhuti Bhusana; Soren, Ramachandra; Sharma, Nagendra K.; Organic & biomolecular chemistry 17 (2019) 6497–6505; doi:10.1039/c9ob00915a

data_7156895
_publ_section_title
;
 BODIPY analogues: synthesis and photophysical studies of difluoro boron
 complexes from 2-aminotropone scaffolds through N,O-chelation.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6497
_journal_page_last               6505
_journal_paper_doi               10.1039/c9ob00915a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C16 H11 B F2 N2 O'
_chemical_formula_sum            'C16 H11 B F2 N2 O'
_chemical_formula_weight         296.10
_chemical_name_systematic        RCS-48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-27
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2019-01-05 deposited with the CCDC.    2019-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.772(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0792(4)
_cell_length_b                   7.4313(4)
_cell_length_c                   26.3653(14)
_cell_measurement_reflns_used    5659
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.6430
_cell_measurement_theta_min      3.9990
_cell_volume                     1377.34(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9964
_diffrn_measured_fraction_theta_max 0.8227
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     24.00  68.00   0.50   36.03    --    3.67  42.00 170.00   88
  2  \w    -68.00  -4.00   0.50   36.03    --   -3.98 -42.00  18.00  128
  3  \w     -4.00  34.00   0.50   36.03    --    3.67 -99.00  60.00   76
  4  \w      1.00  27.00   0.50   36.03    --   -3.98 -99.00-120.00   52
  5  \w    -65.00   6.00   0.50   36.03    --   -3.98 -57.00 -90.00  142
  6  \w    -15.00  56.00   0.50   36.03    --   -3.98  57.00-150.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0663285000
_diffrn_orient_matrix_UB_12      0.0710187000
_diffrn_orient_matrix_UB_13      0.0011177000
_diffrn_orient_matrix_UB_21      -0.0710442000
_diffrn_orient_matrix_UB_22      -0.0524710000
_diffrn_orient_matrix_UB_23      -0.0143411000
_diffrn_orient_matrix_UB_31      -0.0271557000
_diffrn_orient_matrix_UB_32      -0.0362392000
_diffrn_orient_matrix_UB_33      0.0229508000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13111
_diffrn_reflns_theta_full        26.3657
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.45
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.4277
_exptl_crystal_description       needle
_exptl_crystal_F_000             608.3596
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0002
_exptl_crystal_size_min          0.0001
_refine_diff_density_max         0.1952
_refine_diff_density_min         -0.2249
_refine_diff_density_rms         0.0345
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             5.9096
_refine_ls_goodness_of_fit_ref   0.8420
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8420
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.0017
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.1867
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                2436
_reflns_number_total             2802
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob00915a2.cif
_cod_data_source_block           3i
_cod_depositor_comments
'Adding full bibliography for 7156891--7156896.cif.'
_cod_database_code               7156895
_chemical_oxdiff_formula         'C64 H44 B4 F8 N8 O4 '
_diffrn_oxdiff_ac3_digest_frames
;
016c776e7dadc1c278894037c0d999e091000255313
;
_diffrn_oxdiff_ac3_digest_hkl
;
015161a5a47863a410a3b9c266e7a6bd001842
;
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C12(H12), C2(H2), C14(H14), C5(H5), C10(H10), C16(H16),
 C15(H15), C3(H3), C4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.620