Circularly Polarized Luminescence from Helical N,O-Boron-Chelated Dipyrromethenes (BODIPY) Derivatives
Wang, Ling-Yun; Liu, Zheng Fei; Teng, Kun-Xu; Niu, Li-Ya; Yang, Qing-Zheng; Chemical Communications  (2022) –; doi:10.1039/D1CC06051A

data_7129745
_publ_section_title
;
 Circularly Polarized Luminescence from Helical N,O-Boron-Chelated
 Dipyrromethenes (BODIPY) Derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06051A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H24 B Cl2 F N2 O2'
_chemical_formula_sum            'C39 H24 B Cl2 F N2 O2'
_chemical_formula_weight         653.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2799c7
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-02-23 deposited with the CCDC.	2022-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.414(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.0101(4)
_cell_length_b                   10.3606(2)
_cell_length_c                   13.4292(4)
_cell_measurement_reflns_used    8484
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.8450
_cell_measurement_theta_min      3.7690
_cell_volume                     1592.09(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_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    -54.00  25.00   0.50    0.05    --  -47.95  74.00  87.00  158
  2  \w     50.00 102.00   0.50    0.05    --   47.95  74.00  87.00  104
  3  \w     99.00 175.00   0.50    0.10    --  104.75  74.00  87.00  152
  4  \w     91.00 178.00   0.50    0.10    --  104.75  15.00  30.00  174
  5  \w     76.00 108.00   0.50    0.10    --  104.75 -77.00 120.00   64
  6  \w     41.00  67.00   0.50    0.10    --  104.75 -61.00 120.00   52
  7  \w     32.00  63.00   0.50    0.10    --  104.75 -77.00 120.00   62
  8  \w     46.00  87.00   0.50    0.10    --  104.75 -74.00 -41.00   82
  9  \w     41.00  73.00   0.50    0.10    --  104.75 -61.00 -30.00   64
 10  \w    -22.00  69.00   0.50    0.05    --   47.95 -74.00 -41.00  182
 11  \w    -67.00 -30.00   0.50    0.10    -- -102.00  61.00 -60.00   74
 12  \w    -69.00 -43.00   0.50    0.10    -- -102.00  61.00 -30.00   52
 13  \w    -94.00 -54.00   0.50    0.10    -- -102.00  74.00  87.00   80
 14  \w    -68.00 -29.00   0.50    0.10    -- -102.00  61.00  90.00   78
 15  \w    -68.00 -35.00   0.50    0.10    -- -102.00  61.00 150.00   66
 16  \w   -111.00 -85.00   0.50    0.10    -- -102.00 -61.00  30.00   52
 17  \w    -97.00 -72.00   0.50    0.05    --  -47.95 -74.00 -41.00   50
 18  \w    -64.00 -31.00   0.50    0.10    -- -102.00  61.00-150.00   66
 19  \w    -98.00 -73.00   0.50    0.10    -- -102.00  77.00-180.00   50
 20  \w   -175.00-150.00   0.50    0.10    -- -102.00 -74.00 -41.00   50
 21  \w   -166.00-125.00   0.50    0.10    -- -102.00 -61.00  30.00   82
 22  \w   -147.00-114.00   0.50    0.10    -- -102.00 -45.00  30.00   66
 23  \w   -120.00 -72.00   0.50    0.05    --  -47.95-125.00 120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0728304000
_diffrn_orient_matrix_UB_12      -0.1117019000
_diffrn_orient_matrix_UB_13      -0.0099241000
_diffrn_orient_matrix_UB_21      -0.1077014000
_diffrn_orient_matrix_UB_22      -0.0477353000
_diffrn_orient_matrix_UB_23      -0.1077979000
_diffrn_orient_matrix_UB_31      0.0345703000
_diffrn_orient_matrix_UB_32      0.0859653000
_diffrn_orient_matrix_UB_33      -0.0728583000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10899
_diffrn_reflns_point_group_measured_fraction_full 0.749
_diffrn_reflns_point_group_measured_fraction_max 0.706
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.931
_diffrn_reflns_theta_min         3.742
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.198
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic purple'
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1241 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(10)
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         4690
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0468P)^2^+0.2951P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.394
_reflns_Friedel_fraction_full    0.467
_reflns_Friedel_fraction_max     0.424
_reflns_number_gt                4545
_reflns_number_total             4690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06051a2.cif
_cod_data_source_block           20200824h
_cod_original_cell_volume        1592.10(9)
_cod_database_code               7129745
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1n1o1b1f1Cl1
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.734
_diffrn_oxdiff_digest_frames
;
01253d1be5e7fe13239d19e6ac9d08b12500158acf9
;
_diffrn_oxdiff_digest_hkl
;
0187ee5a653e87770dfb3c6430bb45c91775ff
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C15(H15),
 C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C28(H28), C29(H29), C31(H31),
  C32(H32), C35(H35), C36(H36), C38(H38), C39(H39)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_shelx_res_checksum              80905
_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 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.704