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_7156896
_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         '2(C13 H16 B F2 N O3)'
_chemical_formula_sum            'C26 H32 B2 F4 N2 O6'
_chemical_formula_weight         566.15
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-11-24
_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                98.0330(10)
_cell_angle_beta                 94.918(2)
_cell_angle_gamma                94.9710(10)
_cell_formula_units_Z            1
_cell_length_a                   8.1582(2)
_cell_length_b                   9.4094(2)
_cell_length_c                   9.4305(2)
_cell_measurement_reflns_used    20024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.2850
_cell_measurement_theta_min      4.7090
_cell_volume                     710.60(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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    -89.00  -2.00   0.50    0.50    --  -38.50 125.00 -61.00  174
  2  \w   -102.00 -13.00   0.50    0.50    --  -38.50 145.00 105.00  178
  3  \w     34.00 113.00   0.50    0.50    --   49.56-145.00  53.00  158
  4  \w     94.00 176.00   0.50    0.50    --  111.00 125.00 -61.00  164
  5  \w     83.00 175.00   0.50    0.50    --  111.00 145.00 105.00  184
  6  \w     46.00 117.00   0.50    0.50    --  111.00-125.00-138.00  142
  7  \w    -44.00  -6.00   0.50    0.50    --   10.00 130.00 100.90   76
  8  \w    -33.00  -6.00   0.50    0.50    --   22.00 132.00-144.23   54
  9  \w      3.00  32.00   0.50    0.50    --   34.00  90.00 -73.24   58
 10  \w     10.00  36.00   0.50    0.50    --   38.00  85.00 -28.83   52
 11  \w     10.00  36.00   0.50    0.50    --   38.00  85.00 133.67   52
 12  \w     11.00  38.00   0.50    0.50    --   38.00  84.00   3.74   54
 13  \w     11.00  39.00   0.50    0.50    --   38.00  83.00-175.02   56
 14  \w   -105.00 -35.00   0.50    0.50    --  -38.50 -37.00  30.00  140
 15  \w    -42.00  28.00   0.50    0.50    --  -38.50  37.00 -30.00  140
 16  \w     18.00  45.00   0.50    0.50    --   42.00  78.00 118.67   54
 17  \w     17.00  45.00   0.50    0.50    --   42.00  80.00  63.19   56
 18  \w     24.00 101.00   0.50    0.50    --   49.56-125.00-138.00  154
 19  \w     26.00 114.00   0.50    0.50    --   49.56  77.00-120.00  176
 20  \w     26.00 114.00   0.50    0.50    --   49.56  77.00 150.00  176
 21  \w     26.00 114.00   0.50    0.50    --   49.56  77.00  90.00  176
 22  \w     31.00 119.00   0.50    0.50    --   54.00  77.00  50.03  176
 23  \w     31.00 118.00   0.50    0.50    --   54.00  76.00  -7.71  174
 24  \w     35.00 122.00   0.50    0.50    --   58.00  76.00-116.88  174
 25  \w     35.00 122.00   0.50    0.50    --   58.00  76.00  98.61  174
 26  \w     37.00 122.00   0.50    0.50    --   58.00  74.00 -69.90  170
 27  \w     41.00 121.00   0.50    0.50    --   58.00  68.00  65.36  160
 28  \w     35.00 122.00   0.50    0.50    --   58.00  76.00 151.89  174
 29  \w     35.00 122.00   0.50    0.50    --   58.00  76.00 -91.85  174
 30  \w     39.00 126.00   0.50    0.50    --   62.00  76.00-178.98  174
 31  \w     39.00 127.00   0.50    0.50    --   62.00  77.00 -36.38  176
 32  \w     45.00 125.00   0.50    0.50    --   62.00  67.00 -95.12  160
 33  \w     43.00 130.00   0.50    0.50    --   66.00  76.00 -50.64  174
 34  \w     50.00  95.00   0.50    0.50    --   70.00  76.00-165.32   90
 35  \w     60.00  86.00   0.50    0.50    --   74.00  69.00  93.19   52
 36  \w     61.00 100.00   0.50    0.50    --   78.00  67.00  35.32   78
 37  \w    113.00 139.00   0.50    0.50    --   78.00  67.00-138.79   52
 38  \w     61.00  93.00   0.50    0.50    --   78.00  67.00-138.79   64
 39  \w     61.00  87.00   0.50    0.50    --   82.00  76.00  98.29   52
 40  \w     68.00 101.00   0.50    0.50    --   82.00  63.00  13.18   66
 41  \w     72.00 111.00   0.50    0.50    --   86.00  65.00 -37.01   78
 42  \w     80.00 138.00   0.50    0.50    --   94.00  62.00 138.11  116
 43  \w     77.00 109.00   0.50    0.50    --   98.00  77.00  67.74   64
 44  \w    124.00 174.00   0.50    0.50    --  111.00  77.00-120.00  100
 45  \w     49.00  78.00   0.50    0.50    --  111.00 -77.00 -30.00   58
 46  \w     89.00 115.00   0.50    0.50    --  111.00  77.00-120.00   52
 47  \w     98.00 124.00   0.50    0.50    --  111.00  61.00-150.00   52
 48  \w     44.00  73.00   0.50    0.50    --  111.00-111.00 150.00   58
 49  \w    123.00 149.00   0.50    0.50    --  111.00  77.00  30.00   52
 50  \w    129.00 175.00   0.50    0.50    --  111.00  77.00 -30.00   92
 51  \w     87.00 112.00   0.50    0.50    --  111.00-111.00 -60.00   50
 52  \w     53.00  82.00   0.50    0.50    --  111.00-111.00 -60.00   58
 53  \w     48.00  99.00   0.50    0.50    --  111.00 -45.00 -60.00  102
 54  \w     79.00 113.00   0.50    0.50    --  111.00-111.00 150.00   68
 55  \w     89.00 115.00   0.50    0.50    --  111.00  77.00  30.00   52
 56  \w    132.00 166.00   0.50    0.50    --  111.00  61.00-150.00   68
 57  \w    146.00 176.00   0.50    0.50    --  111.00  77.00  90.00   60
 58  \w     94.00 134.00   0.50    0.50    --  111.00 -77.00 -30.00   80
 59  \w     88.00 126.00   0.50    0.50    --  111.00  77.00 150.00   76
 60  \w     88.00 122.00   0.50    0.50    --  111.00  77.00  90.00   68
 61  \w    131.00 160.00   0.50    0.50    --  111.00  77.00 -90.00   58
 62  \w     88.00 114.00   0.50    0.50    --  111.00  77.00 -30.00   52
 63  \w     89.00 130.00   0.50    0.50    --  111.00  77.00 120.00   82
 64  \w     90.00 138.00   0.50    0.50    --  111.00  77.00-180.00   96
 65  \w     88.00 114.00   0.50    0.50    --  111.00  77.00 -90.00   52
 66  \w    100.00 127.00   0.50    0.50    --  111.00  61.00-120.00   54
 67  \w     47.00  87.00   0.50    0.50    --  111.00 -94.00 -60.00   80
 68  \w    137.00 175.00   0.50    0.50    --  111.00  77.00-150.00   76
 69  \w     82.00 108.00   0.50    0.50    --  111.00 -15.00 150.00   52
 70  \w    100.00 126.00   0.50    0.50    --  111.00  61.00  90.00   52
 71  \w     89.00 115.00   0.50    0.50    --  111.00  77.00-150.00   52
 72  \w     88.00 114.00   0.50    0.50    --  111.00 -30.00 -30.00   52
 73  \w     98.00 133.00   0.50    0.50    --  111.00  61.00 -60.00   70
 74  \w     50.00  83.00   0.50    0.50    --  111.00 -30.00 -30.00   66
 75  \w     87.00 113.00   0.50    0.50    --  111.00-111.00-120.00   52
 76  \w     44.00  79.00   0.50    0.50    --  111.00-111.00-120.00   70
 77  \w     84.00 109.00   0.50    0.50    --  111.00 -94.00  30.00   50
 78  \w     78.00 108.00   0.50    0.50    --  111.00 -94.00-180.00   60
 79  \w     48.00  73.00   0.50    0.50    --  111.00 -94.00-180.00   50
 80  \w    146.00 172.00   0.50    0.50    --  111.00  15.00 120.00   52
 81  \w     81.00 114.00   0.50    0.50    --  111.00 -45.00 -30.00   66
 82  \w     88.00 123.00   0.50    0.50    --  111.00  77.00 -60.00   70
 83  \w    109.00 138.00   0.50    0.50    --  111.00  45.00-120.00   58
 84  \w    144.00 170.00   0.50    0.50    --  111.00  45.00-120.00   52
 85  \w     67.00 101.00   0.50    0.50    --  111.00 -94.00   0.00   68
 86  \w     95.00 133.00   0.50    0.50    --  111.00 -77.00-150.00   76
 87  \w    150.00 175.00   0.50    0.50    --  111.00  77.00  60.00   50
 88  \w     79.00 112.00   0.50    0.50    --  111.00-111.00-180.00   66
 89  \w     92.00 118.00   0.50    0.50    --  111.00  77.00  60.00   52
 90  \w     43.00  78.00   0.50    0.50    --  111.00 -15.00 150.00   70
 91  \w     52.00  77.00   0.50    0.50    --  111.00 -77.00-150.00   50
 92  \w     57.00 104.00   0.50    0.50    --  111.00 -77.00  90.00   94
 93  \w    104.00 131.00   0.50    0.50    --  111.00  15.00 120.00   54
 94  \w     98.00 135.00   0.50    0.50    --  111.00  61.00   0.00   74
 95  \w     84.00 113.00   0.50    0.50    --  111.00-111.00 -90.00   58
 96  \w    117.00 175.00   0.50    0.50    --  111.00  45.00 120.00  116
 97  \w     99.00 135.00   0.50    0.50    --  111.00  61.00  30.00   72
 98  \w     48.00  77.00   0.50    0.50    --  111.00 -15.00  60.00   58
 99  \w     87.00 114.00   0.50    0.50    --  111.00 -15.00  60.00   54
100  \w    128.00 172.00   0.50    0.50    --  111.00  61.00-180.00   88
101  \w     42.00  68.00   0.50    0.50    --  111.00-111.00 -90.00   52
102  \w    114.00 176.00   0.50    0.50    --  111.00  45.00  60.00  124
103  \w     58.00 144.00   0.50    0.50    --  111.00 178.00-120.00  172
104  \w     99.00 146.00   0.50    0.50    --  111.00  61.00 -90.00   94
105  \w     48.00  74.00   0.50    0.50    --  111.00 -81.00-128.54   52
106  \w     84.00 110.00   0.50    0.50    --  111.00 -81.00-128.54   52
107  \w    107.00 166.00   0.50    0.50    --  111.00  45.00-180.00  118
108  \w    126.00 151.00   0.50    0.50    --  111.00  45.00 -60.00   50
109  \w     89.00 143.00   0.50    0.50    --  111.00  77.00   0.00  108
110  \w     66.00 113.00   0.50    0.50    --  111.00-111.00 120.00   94
111  \w    117.00 163.00   0.50    0.50    --  111.00 102.00  78.43   92
112  \w    101.00 126.00   0.50    0.50    --  111.00  61.00-180.00   50
113  \w     52.00  78.00   0.50    0.50    --  111.00 -45.00 -30.00   52
114  \w     65.00  90.00   0.50    0.50    --  111.00-145.00  53.00   50
;
_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      -0.0384707000
_diffrn_orient_matrix_UB_12      -0.1652662000
_diffrn_orient_matrix_UB_13      -0.0290349000
_diffrn_orient_matrix_UB_21      -0.0276496000
_diffrn_orient_matrix_UB_22      0.0057442000
_diffrn_orient_matrix_UB_23      -0.1626788000
_diffrn_orient_matrix_UB_31      0.1845035000
_diffrn_orient_matrix_UB_32      -0.0164450000
_diffrn_orient_matrix_UB_33      -0.0134562000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23088
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.912
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.924
_diffrn_reflns_theta_min         4.759
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24227
_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            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       plate
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 2267 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5644
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1419P)^2^+0.0243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1778
_refine_ls_wR_factor_ref         0.1813
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                5351
_reflns_number_total             5644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00915a2.cif
_cod_data_source_block           3c
_cod_depositor_comments
'Adding full bibliography for 7156891--7156896.cif.'
_cod_database_code               7156896
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C24 H32 B2 F4 N4 O6 '
_diffrn_oxdiff_ac3_digest_frames
;
01e4d20231d73648d14f586067648b505010126ebf0
;
_diffrn_oxdiff_ac3_digest_hkl
;
013c2648a49b287c1d8da56cb3861be35ee6b5
;
_reflns_odcompleteness_completeness 97.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7AA(H7AA), C8AA(H8AA), C9(H9), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C5AA(H5AA), C6(H6), C5(H5), C4(H4), C4AA(H4AA), C3(H3), C2(H2), C1AA(H1AA),
 C3AA(H3AA), C2AA(H2AA)
2.c Idealised Me refined as rotating group:
 C0BA(H0BA,H0BB,H0BC), C9AA(H9AA,H9AB,H9AC), C2BA(H2BA,H2BB,H2BC), C10(H10A,
 H10B,H10C), C13(H13A,H13B,H13C), C11(H11A,H11B,H11C)
;
_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 4.294
_oxdiff_exptl_absorpt_empirical_full_min 0.325