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_7129746
_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.cc2799f9
_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                 118.391(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.1863(4)
_cell_length_b                   10.3824(2)
_cell_length_c                   13.6545(5)
_cell_measurement_reflns_used    5900
_cell_measurement_temperature    301.13(11)
_cell_measurement_theta_max      74.2960
_cell_measurement_theta_min      3.6570
_cell_volume                     1644.53(11)
_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      air
_diffrn_ambient_temperature      301.13(11)
_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 0.966
_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    -51.00 -26.00   0.50    0.10    --  -47.95  48.00 113.00   50
  2  \w    -17.00  25.00   0.50    0.10    --  -47.95  48.00 113.00   84
  3  \w   -118.00 -66.00   0.50    0.10    --  -47.95 -48.00 -34.00  104
  4  \w    -63.00 -35.00   0.50    0.10    --  -47.95 -48.00 -34.00   56
  5  \w     -8.00  17.00   0.50    0.10    --   47.95 -48.00 -34.00   50
  6  \w     91.00 177.00   0.50    0.50    --  104.75  48.00 113.00  172
  7  \w    -24.00  28.00   0.50    0.10    --  -47.95  19.00 -90.00  104
  8  \w   -119.00 -74.00   0.50    0.10    --  -47.95-125.00 -90.00   90
  9  \w   -119.00 -72.00   0.50    0.10    --  -47.95-125.00  90.00   94
 10  \w     72.00 101.00   0.50    0.10    --   47.95  48.00 113.00   58
 11  \w   -102.00 -29.00   0.50    0.50    -- -102.00  77.00-180.00  146
 12  \w    -60.00 -32.00   0.50    0.50    -- -102.00  61.00-120.00   56
 13  \w   -175.00 -86.00   0.50    0.50    -- -102.00 -61.00  60.00  178
 14  \w   -154.00-118.00   0.50    0.50    -- -102.00 -61.00  90.00   72
 15  \w    -68.00 -42.00   0.50    0.50    -- -102.00  61.00  60.00   52
 16  \w   -113.00 -86.00   0.50    0.50    -- -102.00 -61.00  90.00   54
 17  \w    -99.00 -74.00   0.50    0.50    -- -102.00  77.00  30.00   50
 18  \w    -54.00 -29.00   0.50    0.50    -- -102.00  77.00  30.00   50
 19  \w   -172.00-111.00   0.50    0.50    -- -102.00 -48.00 -34.00  122
 20  \w     70.00 109.00   0.50    0.50    --  104.75 -94.00 150.00   78
 21  \w     33.00  58.00   0.50    0.50    --  104.75 -94.00 150.00   50
 22  \w     32.00  72.00   0.50    0.50    --  104.75 -61.00 -30.00   80
 23  \w    140.00 177.00   0.50    0.50    --  104.75  30.00-150.00   74
 24  \w    104.00 137.00   0.50    0.50    --  104.75  30.00-150.00   66
 25  \w     32.00  70.00   0.50    0.50    --  104.75 -61.00-180.00   76
 26  \w     38.00  73.00   0.50    0.50    --  104.75 -61.00 -90.00   70
 27  \w     40.00  68.00   0.50    0.50    --  104.75 -61.00-150.00   56
;
_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      -0.1185525000
_diffrn_orient_matrix_UB_12      0.0667912000
_diffrn_orient_matrix_UB_13      -0.0505932000
_diffrn_orient_matrix_UB_21      0.0211400000
_diffrn_orient_matrix_UB_22      0.0570855000
_diffrn_orient_matrix_UB_23      -0.0928604000
_diffrn_orient_matrix_UB_31      -0.0559526000
_diffrn_orient_matrix_UB_32      -0.1196093000
_diffrn_orient_matrix_UB_33      -0.0725162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12505
_diffrn_reflns_point_group_measured_fraction_full 0.799
_diffrn_reflns_point_group_measured_fraction_max 0.758
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.897
_diffrn_reflns_theta_min         3.680
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48251
_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 dark purple'
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(13)
_refine_ls_extinction_coef       0.0014(4)
_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   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5178
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0548P)^2^+0.0287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.484
_reflns_Friedel_fraction_full    0.574
_reflns_Friedel_fraction_max     0.524
_reflns_number_gt                4498
_reflns_number_total             5178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06051a2.cif
_cod_data_source_block           20200910a
_cod_original_cell_volume        1644.54(11)
_cod_database_code               7129746
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1n1o1B1F1Cl1
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.568
_diffrn_oxdiff_digest_frames
;
01906ab4e2db5f3a4dd2677f18248a3c6902192a947
;
_diffrn_oxdiff_digest_hkl
;
01f5f7f023d13b77755e295b4c11405112017d
;
_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              12684
_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 3.273
_oxdiff_exptl_absorpt_empirical_full_min 0.567