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_7129747
_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         'C31 H19 B Cl3 F N2 O2'
_chemical_formula_sum            'C31 H19 B Cl3 F N2 O2'
_chemical_formula_weight         587.64
_chemical_name_common            P1
_chemical_name_systematic        M1
_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_creation_date             2019-12-24
_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                 104.368(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6816(3)
_cell_length_b                   20.2007(5)
_cell_length_c                   12.8842(3)
_cell_measurement_reflns_used    5697
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.8470
_cell_measurement_theta_min      4.1470
_cell_volume                     2693.14(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.970
_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    -68.00  26.00   1.00    1.00    --  -41.49  77.00  30.00   94
  2  \w     37.00  72.00   1.00    1.00    --   41.49-125.00 -60.00   35
  3  \w     15.00 122.00   1.00    1.00    --   41.49  19.00-120.00  107
  4  \w    106.00 177.00   1.00    2.00    --  104.69  45.00-150.00   71
  5  \w    115.00 163.00   1.00    2.00    --  104.69 125.00   0.00   48
  6  \w     40.00 100.00   1.00    2.00    --  104.69 -30.00  30.00   60
  7  \w     74.00 170.00   1.00    2.00    --  104.69  77.00 -30.00   96
  8  \w     58.00 114.00   1.00    2.00    --  104.69 -61.00-150.00   56
  9  \w    131.00 156.00   1.00    2.00    --  104.69 125.00 -30.00   25
 10  \w     38.00 118.00   1.00    2.00    --  104.69-125.00  60.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1261907000
_diffrn_orient_matrix_UB_12      -0.0183310000
_diffrn_orient_matrix_UB_13      -0.0304874000
_diffrn_orient_matrix_UB_21      0.0123228000
_diffrn_orient_matrix_UB_22      -0.0624933000
_diffrn_orient_matrix_UB_23      0.0704509000
_diffrn_orient_matrix_UB_31      -0.0779259000
_diffrn_orient_matrix_UB_32      -0.0397263000
_diffrn_orient_matrix_UB_33      -0.0966597000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10769
_diffrn_reflns_point_group_measured_fraction_full 0.704
_diffrn_reflns_point_group_measured_fraction_max 0.676
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.024
_diffrn_reflns_theta_min         3.541
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.418
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (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    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.004(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     723
_refine_ls_number_reflns         7161
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0329P)^2^+0.4067P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0798
_reflns_Friedel_coverage         0.354
_reflns_Friedel_fraction_full    0.392
_reflns_Friedel_fraction_max     0.365
_reflns_number_gt                6763
_reflns_number_total             7161
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06051a2.cif
_cod_data_source_block           20191216a
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7129747
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1n1o1F1Cl1B1
_shelx_estimated_absorpt_t_max   0.726
_shelx_estimated_absorpt_t_min   0.548
_reflns_odcompleteness_completeness 99.94
_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:
 C2(H2), C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15),
 C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28), C30(H30), C31(H31),
  C33(H33), C34(H34), C38(H38), C39(H39), C41(H41), C42(H42), C45(H45),
 C46(H46), C51(H51), C52(H52), C54(H54), C55(H55), C58(H58), C59(H59), C61(H61),
  C62(H62)
2.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C43(H43A,H43B,H43C)
;
_shelx_res_checksum              67098
_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 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.598