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_7156894
_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         'C13 H11 B F2 N2 O'
_chemical_formula_sum            'C13 H11 B F2 N2 O'
_chemical_formula_weight         260.07
_chemical_name_systematic        triclinic
_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_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-22
_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                62.940(2)
_cell_angle_beta                 89.372(2)
_cell_angle_gamma                69.175(2)
_cell_formula_units_Z            2
_cell_length_a                   8.8495(2)
_cell_length_b                   9.1023(2)
_cell_length_c                   9.2653(2)
_cell_measurement_reflns_used    6984
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.9900
_cell_measurement_theta_min      5.4140
_cell_volume                     610.93(3)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.0
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9774
_diffrn_measured_fraction_theta_max 0.9774
_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    -42.00  28.00   0.50    0.20    --  -38.50  37.00   6.00  140
  2  \w   -105.00 -35.00   0.50    0.20    --  -38.50 -37.00-149.00  140
  3  \w    -17.00  53.00   0.50    0.20    --   49.31 -37.00-149.00  140
  4  \w     46.00 116.00   0.50    0.20    --   49.31  37.00   6.00  140
  5  \w     36.00 106.00   0.50    1.00    --  102.63 -37.00-149.00  140
  6  \w    100.00 169.00   0.50    1.00    --  102.63  37.00   6.00  138
  7  \w   -105.00 -35.00   0.50    0.20    --  -38.50 -37.00 150.00  140
  8  \w     24.00 100.00   0.50    0.20    --   49.31-125.00  60.00  152
  9  \w     38.00 112.00   0.50    0.20    --   49.31  57.00-150.00  148
 10  \w    -20.00  55.00   0.50    0.20    --   49.31 -19.00-120.00  150
 11  \w     98.00 167.00   0.50    1.00    --  102.63  45.00-150.00  138
 12  \w     34.00 110.00   0.50    1.00    --  102.63 -94.00 -90.00  152
 13  \w     38.00 118.00   0.50    1.00    --  102.63-125.00-150.00  160
 14  \w     40.00 116.00   0.50    1.00    --  102.63 -61.00 150.00  152
 15  \w     38.00 118.00   0.50    1.00    --  102.63-125.00 -60.00  160
 16  \w     40.00 116.00   0.50    1.00    --  102.63 -61.00   0.00  152
 17  \w     38.00 118.00   0.50    1.00    --  102.63-125.00  30.00  160
 18  \w     34.00 111.00   0.50    1.00    --  102.63 -15.00  30.00  154
 19  \w     98.00 167.00   0.50    1.00    --  102.63  45.00  60.00  138
 20  \w     34.00 110.00   0.50    1.00    --  102.63 -94.00 150.00  152
 21  \w     35.00 106.00   0.50    1.00    --  102.63 -30.00  60.00  142
 22  \w     35.00 106.00   0.50    1.00    --  102.63 -30.00-120.00  142
 23  \w     98.00 167.00   0.50    1.00    --  102.63  45.00-180.00  138
 24  \w     98.00 167.00   0.50    1.00    --  102.63  45.00-120.00  138
 25  \w     38.00 107.00   0.50    1.00    --  102.63 -45.00-120.00  138
 26  \w     38.00 126.00   0.50    1.00    --  102.63 -77.00   0.00  176
 27  \w     26.00 114.00   0.50    0.20    --   49.31  77.00 -90.00  176
 28  \w     26.00 114.00   0.50    0.20    --   49.31  77.00  30.00  176
 29  \w     26.00 114.00   0.50    0.20    --   49.31  77.00 150.00  176
 30  \w     26.00 114.00   0.50    0.20    --   49.31  77.00 -30.00  176
 31  \w     26.00 114.00   0.50    0.20    --   49.31  77.00  90.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9421
_diffrn_reflns_theta_full        75.3367
_diffrn_reflns_theta_max         75.34
_diffrn_reflns_theta_min         5.44
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60886
_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 light white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.4136
_exptl_crystal_description       needle
_exptl_crystal_F_000             269.0055
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_refine_diff_density_max         0.1187
_refine_diff_density_min         -0.2152
_refine_diff_density_rms         0.0472
_refine_ls_d_res_high            0.7969
_refine_ls_d_res_low             8.1345
_refine_ls_goodness_of_fit_ref   1.1434
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1434
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0460P)^2^+0.0662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              11
_reflns_limit_k_min              -9
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2200
_reflns_number_total             2469
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob00915a2.cif
_cod_data_source_block           3h
_cod_depositor_comments
'Adding full bibliography for 7156891--7156896.cif.'
_cod_database_code               7156894
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C3(H3), C5(H5), C11(H11), C4(H4), C2(H2)
;
_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
;