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_7156892
_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         'C11 H12 B F2 N O3'
_chemical_formula_sum            'C11 H12 B F2 N O3'
_chemical_formula_weight         255.04
_chemical_name_systematic        RCS-21
_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     direct
_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                 97.809(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1705(7)
_cell_length_b                   12.9185(4)
_cell_length_c                   7.3648(2)
_cell_measurement_reflns_used    4594
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.2610
_cell_measurement_theta_min      4.7760
_cell_volume                     1241.45(8)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      298.0
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9661
_diffrn_measured_fraction_theta_max 0.9661
_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    -93.00  -6.00   0.50    4.50    --  -38.50 131.00 -63.00  174
  2  \w    -97.00 -10.00   0.50    4.50    --  -38.50 138.00 112.00  174
  3  \w     28.00 104.00   0.50    4.50    --   49.56-131.00-133.00  152
  4  \w     87.00 169.00   0.50   18.00    --  106.38 138.00 112.00  164
  5  \w     43.00 124.00   0.50   18.00    --  106.38-131.00-133.00  162
  6  \w     91.00 170.00   0.50   18.00    --  106.38 131.00 -63.00  158
  7  \w     44.00 128.00   0.50   18.00    --  106.38-138.00  50.00  168
  8  \w   -101.00 -27.00   0.50    4.50    --  -38.50 -57.00 -60.00  148
  9  \w   -103.00 -75.00   0.50    4.50    --  -38.50 -37.00  30.00   56
 10  \w    -70.00 -37.00   0.50    4.50    --  -38.50 -37.00  30.00   66
 11  \w     43.00 113.00   0.50    4.50    --   49.56  57.00 -60.00  140
 12  \w     46.00  71.00   0.50    4.50    --   49.56-138.00  50.00   50
 13  \w    137.00 168.00   0.50   18.00    --  106.38  15.00 120.00   62
 14  \w     73.00  99.00   0.50   18.00    --  106.38 -94.00  60.00   52
 15  \w     43.00  68.00   0.50   18.00    --  106.38 -45.00 150.00   50
 16  \w     46.00 111.00   0.50   18.00    --  106.38 -45.00  30.00  130
 17  \w     50.00  97.00   0.50   18.00    --  106.38 -61.00-180.00   94
 18  \w    103.00 173.00   0.50   18.00    --  106.38  30.00-180.00  140
 19  \w    119.00 153.00   0.50   18.00    --  106.38  45.00-120.00   68
 20  \w     43.00 111.00   0.50   18.00    --  106.38 -45.00 -30.00  136
 21  \w     74.00 110.00   0.50   18.00    --  106.38 -45.00 150.00   72
 22  \w    105.00 171.00   0.50   18.00    --  106.38  45.00-150.00  132
;
_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  0.0828
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8441
_diffrn_reflns_theta_full        74.4768
_diffrn_reflns_theta_max         74.48
_diffrn_reflns_theta_min         3.39
_exptl_absorpt_coefficient_mu    1.005
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03172
_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    1.3644
_exptl_crystal_description       needle
_exptl_crystal_F_000             530.1697
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_refine_diff_density_max         0.4085
_refine_diff_density_min         -0.3611
_refine_diff_density_rms         0.0967
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             13.0484
_refine_ls_goodness_of_fit_ref   1.2109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.2109
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0974
_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          0.2898
_refine_ls_wR_factor_ref         0.3107
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1794
_reflns_number_total             2449
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9ob00915a2.cif
_cod_data_source_block           3a
_cod_depositor_comments
'Adding full bibliography for 7156891--7156896.cif.'
_cod_database_code               7156892
_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 Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C5(H5), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 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
;