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_7156893
_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         'C12 H14 B F2 N O3'
_chemical_formula_sum            'C12 H14 B F2 N O3'
_chemical_formula_weight         269.07
_chemical_name_systematic        NKS_RCS_ALA
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.5273(5)
_cell_length_b                   7.7581(4)
_cell_length_c                   24.7812(15)
_cell_measurement_reflns_used    3075
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8980
_cell_measurement_theta_min      3.5890
_cell_volume                     2600.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9571
_diffrn_measured_fraction_theta_max 0.9571
_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    -98.00 -16.00   0.50    8.00    --  -38.50 139.00 160.00  164
  2  \w    -50.00 -25.00   0.50    8.00    --  -38.50 130.00 -13.00   50
  3  \w     42.00  67.00   0.50    8.00    --   49.31-130.00 -85.00   50
  4  \w     54.00  93.00   0.50    8.00    --   49.31-139.00 100.00   78
  5  \w     86.00 111.00   0.50   30.00    --  106.38-139.00 100.00   50
  6  \w     99.00 170.00   0.50   30.00    --  106.38 130.00 -13.00  142
  7  \w    123.00 168.00   0.50   30.00    --  106.38 139.00 160.00   90
  8  \w   -100.00 -44.00   0.50    8.00    --  -38.50 -57.00 -90.00  112
  9  \w     -7.00  20.00   0.50    8.00    --  -38.50  77.00-150.00   54
 10  \w    -61.00 -34.00   0.50    8.00    --  -38.50  77.00-150.00   54
 11  \w     13.00  61.00   0.50    8.00    --   49.31 -57.00-120.00   96
 12  \w    113.00 171.00   0.50   30.00    --  106.38 125.00-150.00  116
 13  \w     89.00 114.00   0.50   30.00    --  106.38 -61.00  60.00   50
 14  \w    104.00 175.00   0.50   30.00    --  106.38  30.00 -90.00  142
 15  \w    142.00 168.00   0.50   30.00    --  106.38  45.00 -30.00   52
 16  \w    104.00 129.00   0.50   30.00    --  106.38  45.00 -30.00   50
 17  \w     47.00  88.00   0.50   30.00    --  106.38 -61.00  60.00   82
 18  \w     68.00  95.00   0.50   30.00    --  106.38 -30.00-150.00   54
;
_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      0.0798606000
_diffrn_orient_matrix_UB_12      0.0545941000
_diffrn_orient_matrix_UB_13      0.0409145000
_diffrn_orient_matrix_UB_21      0.0713028000
_diffrn_orient_matrix_UB_22      0.0407908000
_diffrn_orient_matrix_UB_23      -0.0467663000
_diffrn_orient_matrix_UB_31      -0.0388228000
_diffrn_orient_matrix_UB_32      0.1865344000
_diffrn_orient_matrix_UB_33      -0.0017715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10196
_diffrn_reflns_theta_full        74.4605
_diffrn_reflns_theta_max         74.46
_diffrn_reflns_theta_min         3.57
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
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    1.3742
_exptl_crystal_description       needle
_exptl_crystal_F_000             1124.4858
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_refine_diff_density_max         0.2916
_refine_diff_density_min         -0.4282
_refine_diff_density_rms         0.0884
_refine_ls_d_res_high            0.8002
_refine_ls_d_res_low             12.3906
_refine_ls_goodness_of_fit_ref   1.1260
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2546
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1260
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0922
_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^)+(0.2P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2806
_refine_ls_wR_factor_ref         0.3336
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              0
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                1454
_reflns_number_total             2546
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob00915a2.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 7156891--7156896.cif.'
_cod_database_code               7156893
_chemical_oxdiff_formula         'C96 H112 B8 F16 N8 O24 '
_diffrn_oxdiff_ac3_digest_frames
;
01c0cbd288793b922a3a12069b0c882a4400025ed33
;
_diffrn_oxdiff_ac3_digest_hkl
;
015e171b5f4e6dfc99157bc9af0c596509beab
;
_reflns_odcompleteness_completeness 99.52
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C12(H12a,H12b,H12c)
;
_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 5.299
_oxdiff_exptl_absorpt_empirical_full_min 0.198