Inherently chiral belt-shaped conjugated macrocycles with strong fluorescence and circularly polarized luminescence.
Du, Xu-Sheng; Han, Xiao-Ni; Han, Ying; Chen, Chuan-Feng; Chemical communications (Cambridge, England) 59 (2022) 227–230; doi:10.1039/d2cc05504j

data_7131041
_publ_section_title
;
 Inherently chiral belt-shaped conjugated macrocycles with strong
 fluorescence and circularly polarized luminescence.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              227
_journal_page_last               230
_journal_paper_doi               10.1039/d2cc05504j
_journal_volume                  59
_journal_year                    2022
_chemical_formula_moiety         '3(C H2 Cl2), C60 H54'
_chemical_formula_sum            'C63 H60 Cl6'
_chemical_formula_weight         1029.81
_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             2021-11-30
_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.	2022-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                71.467(2)
_cell_angle_beta                 69.769(2)
_cell_angle_gamma                79.6845(19)
_cell_formula_units_Z            2
_cell_length_a                   12.9068(3)
_cell_length_b                   14.7144(3)
_cell_length_c                   16.1660(4)
_cell_measurement_reflns_used    24332
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      76.8790
_cell_measurement_theta_min      3.1860
_cell_volume                     2723.11(12)
_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(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.950
_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     41.00 120.00   0.50    0.05    --   47.68  51.00 -98.00  158
  2  \w    115.00 178.00   0.50    0.09    --  106.75  56.00-170.88  126
  3  \w     95.00 121.00   0.50    0.09    --  106.75  51.00 -98.00   52
  4  \w    125.00 178.00   0.50    0.09    --  106.75  51.00 -98.00  106
  5  \w    125.00 178.00   0.50    0.09    --  106.75  38.00 -60.00  106
  6  \w    136.00 172.00   0.50    0.09    --  106.75  19.00  60.00   72
  7  \w     97.00 123.00   0.50    0.09    --  106.75  19.00  60.00   52
  8  \w     41.00 104.00   0.50    0.09    --  106.75 -99.00 120.00  126
  9  \w     57.00 106.00   0.50    0.09    --  106.75-125.00  90.00   98
 10  \w     20.00  94.00   0.50    0.05    --   47.68-125.00 120.00  148
 11  \w     20.00  92.00   0.50    0.05    --   47.68-125.00  30.00  144
 12  \w     51.00 111.00   0.50    0.09    --  106.75-125.00 -30.00  120
 13  \w     71.00 107.00   0.50    0.09    --  106.75-102.00  58.37   72
 14  \w     36.00  67.00   0.50    0.09    --  106.75-102.00  58.37   62
 15  \w     80.00 105.00   0.50    0.09    --  106.75 -99.00 -60.00   50
 16  \w     39.00  77.00   0.50    0.09    --  106.75 -99.00-120.00   76
 17  \w     34.00  72.00   0.50    0.09    --  106.75-125.00-180.00   76
 18  \w     75.00 112.00   0.50    0.09    --  106.75-125.00-180.00   74
 19  \w     63.00 106.00   0.50    0.09    --  106.75 -99.00-150.00   86
 20  \w     61.00 106.00   0.50    0.09    --  106.75-105.00-153.27   90
 21  \w     79.00 106.00   0.50    0.09    --  106.75 -99.00-120.00   54
 22  \w     60.00 102.00   0.50    0.09    --  106.75 -99.00   0.00   84
 23  \w     36.00  85.00   0.50    0.09    --  106.75 -99.00  90.00   98
 24  \w    -26.00  30.00   0.50    0.05    --   47.68 -19.00 150.00  112
 25  \w     35.00  65.00   0.50    0.09    --  106.75 -57.00 150.00   60
 26  \w     36.00  62.00   0.50    0.09    --  106.75 -57.00  90.00   52
 27  \w     34.00  67.00   0.50    0.09    --  106.75 -57.00 -30.00   66
 28  \w     36.00  65.00   0.50    0.09    --  106.75 -57.00 -60.00   58
 29  \w     35.00  68.00   0.50    0.09    --  106.75 -57.00 -90.00   66
 30  \w     41.00  69.00   0.50    0.09    --  106.75 -57.00-120.00   56
 31  \w     82.00 108.00   0.50    0.09    --  106.75 -77.00 -90.00   52
 32  \w     -6.00  19.00   0.50    0.05    --   47.68 -51.00 115.00   50
 33  \w     34.00  61.00   0.50    0.09    --  106.75 -51.00 115.00   54
 34  \w    -24.00  22.00   0.50    0.05    --  -47.68  51.00 -98.00   92
 35  \w    -62.00  21.00   0.50    0.05    --  -47.68  57.00-150.00  166
 36  \w    -61.00 -35.00   0.50    0.09    -- -104.50  57.00-150.00   52
 37  \w    -61.00 -33.00   0.50    0.09    -- -104.50  57.00 -90.00   56
 38  \w    -62.00 -36.00   0.50    0.09    -- -104.50  57.00 -60.00   52
 39  \w    -60.00 -34.00   0.50    0.09    -- -104.50  57.00   0.00   52
 40  \w    -64.00 -35.00   0.50    0.09    -- -104.50  77.00  90.00   58
 41  \w   -106.00 -81.00   0.50    0.09    -- -104.50 125.00 120.00   50
 42  \w    -67.00 -40.00   0.50    0.09    -- -104.50 125.00 120.00   54
 43  \w   -169.00-102.00   0.50    0.09    -- -104.50 -51.00 115.00  134
 44  \w   -116.00 -64.00   0.50    0.05    --  -47.68 -51.00 115.00  104
 45  \w   -169.00-109.00   0.50    0.09    -- -104.50 -64.00-146.55  120
 46  \w   -164.00-106.00   0.50    0.09    -- -104.50 -47.00-138.97  116
 47  \w   -119.00 -88.00   0.50    0.05    --  -47.68-125.00-180.00   62
;
_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      -0.0211719000
_diffrn_orient_matrix_UB_12      -0.0468784000
_diffrn_orient_matrix_UB_13      -0.0648143000
_diffrn_orient_matrix_UB_21      -0.0983983000
_diffrn_orient_matrix_UB_22      0.0746752000
_diffrn_orient_matrix_UB_23      -0.0097033000
_diffrn_orient_matrix_UB_31      0.0784207000
_diffrn_orient_matrix_UB_32      0.0670349000
_diffrn_orient_matrix_UB_33      -0.0829381000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35753
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.333
_diffrn_reflns_theta_min         3.032
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52246
_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            'clear pale colourless'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       cube
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.359
_refine_diff_density_min         -1.491
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.722
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     638
_refine_ls_number_reflns         10991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.722
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.1003
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3483
_refine_ls_wR_factor_ref         0.3549
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10153
_reflns_number_total             10991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05504j2.cif
_cod_data_source_block           tx9799_auto
_cod_depositor_comments
'Adding full bibliography for 7131041--7131042.cif.'
_cod_original_cell_volume        2723.10(12)
_cod_database_code               7131041
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHO
_diffrn_oxdiff_digest_frames
;
015db567fb90048213dd25b8f304122cb303924d6f5
;
_diffrn_oxdiff_digest_hkl
;
01e92dc8784e56634185aefbf00e44b59c4309
;
_reflns_odcompleteness_completeness 99.87
_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. Others
 Sof(H46A)=Sof(C47A)=Sof(H47C)=Sof(H47D)=1-FVAR(1)
 Sof(H46)=Sof(C47)=Sof(H47A)=Sof(H47B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B), C31(H31A,H31B), C2(H2A,H2B), C8(H8A,H8B),
 C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C29(H29), C13(H13), C23(H23), C39(H39), C40(H40), C19(H19), C48(H48),
 C60(H60), C33(H33), C44(H44), C57(H57), C52(H52), C42(H42), C50(H50), C54(H54),
  C62(H62), C58(H58), C46(H46), C46(H46A)
3.c X=CH2 refined with riding coordinates:
 C43(H43A,H43B), C55(H55A,H55B), C51(H51A,H51B), C59(H59A,H59B), C63(H63A,
 H63B), C47(H47A,H47B), C47A(H47C,H47D)
3.d Idealised Me refined as rotating group:
 C65(H65A,H65B,H65C), C66(H66A,H66B,H66C), C64(H64A,H64B,H64C), C68(H68A,H68B,
 H68C), C69(H69A,H69B,H69C), C67(H67A,H67B,H67C)
;
_shelx_res_checksum              29170
_shelx_hkl_checksum              29885
_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 1.710
_oxdiff_exptl_absorpt_empirical_full_min 0.669