A novel thermally activated delayed fluorescence macrocycle
Zhou, He-Ye; Zhang, Da-Wei; Han, Xiao-Ni; Han, Ying; Chen, Chuan-Feng; Chemical Communications  (2022) –; doi:10.1039/D2CC04618K

data_7130859
_publ_section_title
;
 A novel thermally activated delayed fluorescence macrocycle
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04618K
_journal_year                    2022
_chemical_formula_moiety         'C111 H84 N12'
_chemical_formula_sum            'C111 H84 N12'
_chemical_formula_weight         1585.90
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-06-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-26 deposited with the CCDC.	2022-10-06 downloaded from the CCDC.
;
_cell_angle_alpha                97.7680(10)
_cell_angle_beta                 90.2160(10)
_cell_angle_gamma                109.9910(10)
_cell_formula_units_Z            2
_cell_length_a                   13.0996(2)
_cell_length_b                   18.3840(3)
_cell_length_c                   23.2467(3)
_cell_measurement_reflns_used    35642
_cell_measurement_temperature    170.00(13)
_cell_measurement_theta_max      76.7080
_cell_measurement_theta_min      2.5660
_cell_volume                     5205.23(14)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.954
_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    -82.00  -8.00   0.50    0.50    --  -47.70 111.00  65.00  148
  2  \w     50.00  86.00   0.50    0.50    --   47.70-111.00 -27.00   72
  3  \w     23.00  49.00   0.50    0.50    --   47.70-111.00 -27.00   52
  4  \w   -105.00 -73.00   0.50    1.50    -- -104.50 111.00  65.00   64
  5  \w   -147.00 -89.00   0.50    1.50    -- -104.50-111.00 -27.00  116
  6  \w     88.00 167.00   0.50    1.50    --  107.36 111.00  65.00  158
  7  \w    -61.00  22.00   0.50    0.50    --  -47.70  57.00  30.00  166
  8  \w   -119.00 -74.00   0.50    0.50    --  -47.70-125.00-180.00   90
  9  \w   -118.00 -80.00   0.50    0.50    --  -47.70-125.00  60.00   76
 10  \w   -120.00 -74.00   0.50    0.50    --  -47.70-125.00  30.00   92
 11  \w    -21.00  27.00   0.50    0.50    --  -47.70  19.00 -30.00   96
 12  \w    -40.00  25.00   0.50    0.50    --  -47.70  38.00  90.00  130
 13  \w     36.00  82.00   0.50    0.50    --   47.70  38.00-180.00   92
 14  \w    -26.00  28.00   0.50    0.50    --   47.70 -19.00-150.00  108
 15  \w   -173.00 -94.00   0.50    1.50    -- -104.50 -49.00 -25.35  158
 16  \w   -132.00-106.00   0.50    1.50    -- -104.50 -61.00  84.63   52
 17  \w   -109.00 -81.00   0.50    1.50    -- -104.50 116.00  85.43   56
 18  \w    -99.00 -32.00   0.50    1.50    -- -104.50  77.00  60.00  134
 19  \w   -167.00-101.00   0.50    1.50    -- -104.50 -57.00 -90.00  132
 20  \w   -132.00-106.00   0.50    1.50    -- -104.50 -19.00   0.00   52
 21  \w   -129.00 -38.00   0.50    1.50    -- -104.50 149.00 102.30  182
 22  \w   -161.00-135.00   0.50    1.50    -- -104.50 -19.00   0.00   52
 23  \w   -165.00 -97.00   0.50    1.50    -- -104.50 -44.00-174.19  136
 24  \w   -107.00 -32.00   0.50    1.50    -- -104.50 110.00  -4.78  150
 25  \w    -62.00 -33.00   0.50    1.50    -- -104.50  57.00  30.00   58
 26  \w   -174.00-125.00   0.50    1.50    -- -104.50 -44.00  49.49   98
 27  \w    -58.00 -32.00   0.50    1.50    -- -104.50  57.00 -30.00   52
 28  \w   -173.00-145.00   0.50    1.50    -- -104.50 -61.00  84.63   56
 29  \w    -87.00 -32.00   0.50    1.50    -- -104.50  77.00 -60.00  110
 30  \w     37.00 105.00   0.50    1.50    --  107.36 -99.00-150.00  136
 31  \w     36.00  74.00   0.50    1.50    --  107.36 -99.00 150.00   76
 32  \w     35.00  60.00   0.50    1.50    --  107.36 -57.00-180.00   50
 33  \w     96.00 138.00   0.50    1.50    --  107.36  38.00 150.00   84
 34  \w     56.00  99.00   0.50    1.50    --  107.36 -99.00 -30.00   86
 35  \w     66.00  92.00   0.50    1.50    --  107.36-125.00 -60.00   52
 36  \w     86.00 176.00   0.50    1.50    --  107.36  77.00  30.00  180
 37  \w     37.00  84.00   0.50    1.50    --  107.36-125.00 150.00   94
 38  \w     37.00 111.00   0.50    1.50    --  107.36-125.00 120.00  148
 39  \w     37.00 103.00   0.50    1.50    --  107.36 -99.00-120.00  132
 40  \w     71.00 106.00   0.50    1.50    --  107.36-111.00 -27.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0464328000
_diffrn_orient_matrix_UB_12      0.0834562000
_diffrn_orient_matrix_UB_13      0.0338220000
_diffrn_orient_matrix_UB_21      -0.0618701000
_diffrn_orient_matrix_UB_22      0.0287354000
_diffrn_orient_matrix_UB_23      -0.0431792000
_diffrn_orient_matrix_UB_31      -0.0985656000
_diffrn_orient_matrix_UB_32      -0.0182770000
_diffrn_orient_matrix_UB_33      0.0384543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            68701
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.373
_diffrn_reflns_theta_min         1.921
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'fluorescent light yellow'
_exptl_crystal_density_diffrn    1.012
_exptl_crystal_description       block
_exptl_crystal_F_000             1668
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.00016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1115
_refine_ls_number_reflns         21096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0726
_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^)+(0.0278P)^2^+6.8661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17573
_reflns_number_total             21096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04618k2.cif
_cod_data_source_block           tx10477_auto_sq
_cod_database_code               7130859
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNCl
_diffrn_oxdiff_digest_frames
;
016f0950a5fe41e36b86b422dc435795bd04046e95c
;
_diffrn_oxdiff_digest_hkl
;
01b246188e89029f4578a994f23bb74d17b17f
;
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C33(H33A,H33B), C17(H17A,H17B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C38(H38), C29(H29), C37(H37), C15(H15), C50(H50), C100(H100), C39(H39),
 C134(H134), C21(H21), C49(H49), C28(H28), C40(H40), C46(H46), C101(H101),
 C47(H47), C36(H36), C105(H105), C20(H20), C106(H106), C116(H116), C115(H115),
 C133(H133), C130(H130), C110(H110), C109(H109), C74(H74), C73(H73), C131(H131),
  C132(H132), C64(H64), C68(H68), C77(H77), C62(H62), C80(H80), C81(H81),
 C113(H113), C78(H78), C112(H112), C126(H126), C58(H58), C67(H67), C128(H128),
 C65(H65), C66(H66), C61(H61), C93(H93), C95(H95), C124(H124), C127(H127),
 C99(H99), C125(H125), C89(H89), C59(H59), C92(H92), C98(H98), C60(H60),
 C96(H96), C97(H97), C91(H91), C90(H90)
2.c Idealised Me refined as rotating group:
 C70(H70A,H70B,H70C), C69(H69A,H69B,H69C), C103(H10A,H10B,H10C), C102(H10D,
 H10E,H10F), C136(H13A,H13B,H13C), C135(H13D,H13E,H13F)
;
_shelx_res_checksum              47415
_shelx_hkl_checksum              40425
_shelx_fab_checksum              43192
_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 3.765
_oxdiff_exptl_absorpt_empirical_full_min 0.113