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_7156891
_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         'C9 H8 B F2 N O3'
_chemical_formula_sum            'C9 H8 B F2 N O3'
_chemical_formula_weight         226.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                 90.857(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0433(4)
_cell_length_b                   11.5620(8)
_cell_length_c                   11.6118(8)
_cell_measurement_reflns_used    5212
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.0930
_cell_measurement_theta_min      3.7760
_cell_volume                     945.50(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.972
_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    -76.00  18.00   0.50    4.00    --  -38.50 102.00  -2.00  188
  2  \w      4.00  87.00   0.50    4.00    --   49.31-102.00-106.00  166
  3  \w    101.00 176.00   0.50   16.00    --  106.38 102.00  -2.00  150
  4  \w     37.00 112.00   0.50   16.00    --  106.38-102.00-106.00  150
  5  \w    -44.00  31.00   0.50    4.00    --  -38.50  19.00 -60.00  150
  6  \w     38.00 112.00   0.50    4.00    --   49.31  57.00  90.00  148
  7  \w     44.00 120.00   0.50   16.00    --  106.38 -61.00  90.00  152
  8  \w     38.00 110.00   0.50   16.00    --  106.38 -30.00-150.00  144
  9  \w     42.00 122.00   0.50   16.00    --  106.38-125.00 -30.00  160
 10  \w     42.00 111.00   0.50   16.00    --  106.38 -45.00 -60.00  138
 11  \w     93.00 169.00   0.50   16.00    --  106.38  61.00-120.00  152
 12  \w     38.00 109.00   0.50   16.00    --  106.38 -94.00  30.00  142
 13  \w    103.00 175.00   0.50   16.00    --  106.38  30.00   0.00  144
 14  \w    102.00 171.00   0.50   16.00    --  106.38  45.00 -90.00  138
 15  \w     93.00 169.00   0.50   16.00    --  106.38  61.00 150.00  152
 16  \w     26.00  51.00   0.50    4.00    --   49.31  77.00-150.00   50
 17  \w     26.00 114.00   0.50    4.00    --   49.31  77.00 -30.00  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_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1024985000
_diffrn_orient_matrix_UB_12      0.0111566000
_diffrn_orient_matrix_UB_13      -0.1176240000
_diffrn_orient_matrix_UB_21      -0.1281190000
_diffrn_orient_matrix_UB_22      0.0952027000
_diffrn_orient_matrix_UB_23      0.0494597000
_diffrn_orient_matrix_UB_31      0.1445792000
_diffrn_orient_matrix_UB_32      0.0925843000
_diffrn_orient_matrix_UB_33      -0.0365047000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6207
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.466
_diffrn_reflns_theta_min         5.399
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_description       needle
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.567
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.567
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.1201
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3423
_refine_ls_wR_factor_ref         0.3485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1701
_reflns_number_total             1880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00915a2.cif
_cod_data_source_block           3j
_cod_depositor_comments
'Adding full bibliography for 7156891--7156896.cif.'
_cod_database_code               7156891
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C H N O B F'
_diffrn_oxdiff_ac3_digest_frames
;
01bac81433a7609429229c326363b65922000264e04
;
_diffrn_oxdiff_ac3_digest_hkl
;
0104e3d0b2ec15b07b3b9ef20a5f3ccfdb8009
;
_reflns_odcompleteness_completeness 98.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6), C2(H2), C3(H3A), C5(H5), 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 5.419
_oxdiff_exptl_absorpt_empirical_full_min 0.193