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_7131042
_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), C54 H42'
_chemical_formula_sum            'C57 H48 Cl6'
_chemical_formula_weight         945.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                90
_cell_angle_beta                 117.155(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6999(2)
_cell_length_b                   27.5753(4)
_cell_length_c                   14.7599(2)
_cell_measurement_reflns_used    40680
_cell_measurement_temperature    169.99(11)
_cell_measurement_theta_max      76.1580
_cell_measurement_theta_min      3.1690
_cell_volume                     4961.37(15)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.985
_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    150.00 176.00   0.50    0.73    --  106.75  77.00  60.00   52
  2  \w     85.00 134.00   0.50    0.73    --  106.75  77.00  60.00   98
  3  \w     38.00 117.00   0.50    0.06    --   47.68  38.00 -90.00  158
  4  \w    -23.00  27.00   0.50    0.06    --  -47.68  19.00   0.00  100
  5  \w    -61.00 -36.00   0.50    0.73    -- -104.50  57.00 -30.00   50
  6  \w    -22.00  27.00   0.50    0.06    --  -47.68  19.00  90.00   98
  7  \w     35.00  93.00   0.50    0.73    --  106.75 -99.00  90.00  116
  8  \w     50.00  75.00   0.50    0.73    --  106.75-129.00 102.00   50
  9  \w     35.00  60.00   0.50    0.06    --   47.68-129.00 102.00   50
 10  \w     78.00 104.00   0.50    0.73    --  106.75 -99.00 120.00   52
 11  \w     35.00 102.00   0.50    0.73    --  106.75-125.00   0.00  134
 12  \w     37.00  89.00   0.50    0.73    --  106.75 -99.00   0.00  104
 13  \w     44.00 105.00   0.50    0.73    --  106.75 -99.00 150.00  122
 14  \w     42.00  67.00   0.50    0.06    --   47.68-141.00 -69.00   50
 15  \w     39.00 123.00   0.50    0.73    --  106.75-141.00 -69.00  168
 16  \w     34.00 104.00   0.50    0.73    --  106.75 -99.00 -90.00  140
 17  \w     44.00  81.00   0.50    0.73    --  106.75 -77.00 -90.00   74
 18  \w    -24.00  29.00   0.50    0.06    --   47.68 -19.00 120.00  106
 19  \w     35.00  69.00   0.50    0.73    --  106.75 -57.00 120.00   68
 20  \w     36.00  69.00   0.50    0.73    --  106.75 -57.00  90.00   66
 21  \w     78.00 155.00   0.50    0.73    --  106.75 129.00 175.00  154
 22  \w     75.00 101.00   0.50    0.06    --   47.68 141.00 -12.00   52
 23  \w     97.00 122.00   0.50    0.73    --  106.75 141.00 -12.00   50
 24  \w    -85.00 -38.00   0.50    0.73    -- -104.50 125.00 -30.00   94
 25  \w    -68.00 -32.00   0.50    0.73    -- -104.50 143.00 -54.87   72
 26  \w   -125.00 -90.00   0.50    0.73    -- -104.50 143.00 -54.87   70
 27  \w   -103.00 -60.00   0.50    0.06    --  -47.68 141.00 -12.00   86
 28  \w   -102.00 -77.00   0.50    0.73    -- -104.50 141.00 -12.00   50
 29  \w   -123.00 -33.00   0.50    0.73    -- -104.50 140.00   2.43  180
 30  \w    -75.00 -33.00   0.50    0.73    -- -104.50 144.00  34.66   84
 31  \w    -99.00 -71.00   0.50    0.73    -- -104.50 129.00 175.00   56
 32  \w    -90.00 -33.00   0.50    0.73    -- -104.50 141.00 147.08  114
 33  \w   -123.00 -98.00   0.50    0.73    -- -104.50 141.00 147.08   50
 34  \w   -124.00 -94.00   0.50    0.73    -- -104.50 144.00  34.66   60
 35  \w    -93.00 -46.00   0.50    0.06    --  -47.68 129.00 175.00   94
 36  \w   -161.00-111.00   0.50    0.73    -- -104.50 -47.00 175.10  100
 37  \w   -168.00-142.00   0.50    0.73    -- -104.50 -53.00 167.33   52
 38  \w   -173.00 -94.00   0.50    0.73    -- -104.50 -57.00 120.00  158
 39  \w   -165.00 -90.00   0.50    0.73    -- -104.50 -54.00 127.94  150
 40  \w   -117.00 -90.00   0.50    0.73    -- -104.50 -53.00 167.33   54
 41  \w   -120.00 -25.00   0.50    0.06    --  -47.68 -77.00 120.00  190
 42  \w   -170.00-140.00   0.50    0.73    -- -104.50 -68.00-151.37   60
 43  \w   -119.00 -66.00   0.50    0.06    --  -47.68-141.00 -69.00  106
 44  \w   -142.00-117.00   0.50    0.73    -- -104.50-141.00 -69.00   50
 45  \w   -173.00 -80.00   0.50    0.73    -- -104.50 -92.00  59.60  186
 46  \w   -142.00 -85.00   0.50    0.73    -- -104.50-129.00 102.00  114
 47  \w   -120.00 -73.00   0.50    0.06    --  -47.68-129.00 102.00   94
;
_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      -0.0746011000
_diffrn_orient_matrix_UB_12      -0.0420739000
_diffrn_orient_matrix_UB_13      -0.0010855000
_diffrn_orient_matrix_UB_21      -0.0886675000
_diffrn_orient_matrix_UB_22      0.0366847000
_diffrn_orient_matrix_UB_23      -0.0086596000
_diffrn_orient_matrix_UB_31      -0.0502262000
_diffrn_orient_matrix_UB_32      -0.0023467000
_diffrn_orient_matrix_UB_33      -0.1168916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            71868
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.052
_diffrn_reflns_theta_min         3.205
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.434
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66857
_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    1.266
_exptl_crystal_description       cube
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.049
_refine_diff_density_min         -1.651
_refine_diff_density_rms         0.193
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.244
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         10177
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      2.267
_refine_ls_R_factor_all          0.1564
_refine_ls_R_factor_gt           0.1510
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4300
_refine_ls_wR_factor_ref         0.4451
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9209
_reflns_number_total             10177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc05504j2.cif
_cod_data_source_block           tx9800-a_auto
_cod_depositor_comments
'Adding full bibliography for 7131041--7131042.cif.'
_cod_original_cell_volume        4961.36(16)
_cod_database_code               7131042
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHClO
_diffrn_oxdiff_digest_frames
;
01c739ecd9eb977b09f8b9c37911d0d12e04436084e
;
_diffrn_oxdiff_digest_hkl
;
0156779552b78ac3f298df9b5c9f353ff9ac7f
;
_reflns_odcompleteness_completeness 99.96
_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. Restrained distances
 Cl5-C3 = Cl4-C3 = Cl4-C7 = Cl6-C7
 1.76 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl4 \\sim C3 \\sim C7 \\sim Cl5 \\sim Cl6: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(C7) \\sim Ueq, Uanis(Cl4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(Cl5)
\\sim Ueq, Uanis(Cl6) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(Cl6)=Sof(C7)=Sof(H7A)=Sof(H7B)=1-FVAR(1)
 Sof(Cl5)=Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C28(H28A,H28B), C19(H19A,H19B), C2(H2A,H2B), C6(H6A,H6B), C3(H3A,
 H3B), C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C40(H40), C37(H37), C42(H42), C30(H30), C17(H17), C36(H36),
 C39(H39), C52(H52), C55(H55), C43(H43), C25(H25), C54(H54), C21(H21), C51(H51),
  C48(H48), C45(H45), C46(H46)
5.c Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C61(H61A,H61B,H61C), C59(H59A,H59B,H59C), C60(H60A,H60B,
 H60C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              79886
_shelx_hkl_checksum              41739
_shelx_fab_checksum              14705
_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 1.959
_oxdiff_exptl_absorpt_empirical_full_min 0.492