Facile Synthesis of Homochiral Compounds Integrating Circularly Polarized Luminescence and Two-Photon Excited Fluorescence
Deng, Wen-Ting; Qu, Hang; Huang, Zhe-Yu; Shi, Lin; Tang, Zhiyong; Cao, Xiaoyu; Tao, Jun; Chemical Communications  (2019) –; doi:10.1039/C8CC08947G

data_7122897
_publ_section_title
;
 Facile Synthesis of Homochiral Compounds Integrating Circularly Polarized
 Luminescence and Two-Photon Excited Fluorescence
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08947G
_journal_year                    2019
_chemical_formula_moiety         'C68 H56 Cd N6 O14, C4 H8 O'
_chemical_formula_sum            'C72 H64 Cd N6 O15'
_chemical_formula_weight         1365.69
_chemical_melting_point          ?
_chemical_name_common            R-L-Cd
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-15
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2019-01-16 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                110.664(2)
_cell_angle_beta                 90.320(2)
_cell_angle_gamma                93.114(2)
_cell_formula_units_Z            1
_cell_length_a                   10.1560(3)
_cell_length_b                   12.1202(3)
_cell_length_c                   15.9290(4)
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.0790
_cell_measurement_theta_min      3.9450
_cell_volume                     1831.25(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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 10.4741
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
  1 omega  -49.00   34.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047   37.0000  -30.0000 83

  2 omega   36.00   78.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5047  -99.0000  -60.0000 42

  3 omega   29.00   97.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -45.0000   60.0000 68

  4 omega   78.00  105.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -94.0000   90.0000 27

  5 omega   32.00  109.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -94.0000  -60.0000 77

  6 omega   58.00  117.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446 -125.0000  -60.0000 59

  7 omega   59.00   89.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -30.0000 -120.0000 30

  8 omega   73.00  175.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446   30.0000 -180.0000 102

  9 omega  117.00  177.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  125.0000  -60.0000 60

 10 omega   96.00  123.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  125.0000 -180.0000 27

 11 omega   25.00   91.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -30.0000 -180.0000 66

 12 omega    4.00   42.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5047  -99.0000 -120.0000 38

 13 omega   28.00   99.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -94.0000   60.0000 71

 14 omega   32.00   82.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -45.0000  150.0000 50

 15 omega   76.00  173.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446   45.0000   90.0000 97

 16 omega  111.00  166.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  125.0000  120.0000 55

 17 omega  -70.00   30.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047   57.0000 -180.0000 100

 18 omega -111.00  -21.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5047  -57.0000   30.0000 90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1367547000
_diffrn_orient_matrix_UB_12      -0.0474940000
_diffrn_orient_matrix_UB_13      0.0177915000
_diffrn_orient_matrix_UB_21      -0.0482816000
_diffrn_orient_matrix_UB_22      -0.0107525000
_diffrn_orient_matrix_UB_23      -0.0945790000
_diffrn_orient_matrix_UB_31      0.0454006000
_diffrn_orient_matrix_UB_32      -0.1270832000
_diffrn_orient_matrix_UB_33      -0.0378157000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12438
_diffrn_reflns_point_group_measured_fraction_full 0.590
_diffrn_reflns_point_group_measured_fraction_max 0.572
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.551
_diffrn_reflns_theta_min         3.905
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             706
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.034
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.050(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     851
_refine_ls_number_reflns         8179
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+4.4633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.182
_reflns_Friedel_fraction_full    0.186
_reflns_Friedel_fraction_max     0.176
_reflns_number_gt                8146
_reflns_number_total             8179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08947g2.cif
_cod_data_source_block           R-L-Cd
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'Not measured' was changed to '?' -
the value is undefined or not given.

'_exptl_crystal_density_meas' value 'Not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7122897
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.758
_shelx_estimated_absorpt_t_min   0.758
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C31(H31A,H31B), C65(H65A,H65B), C33(H33A,H33B), C67(H67A,H67B), C72(H72A,
 H72B), C71(H71A,H71B), C69(H69A,H69B), C70(H70A,H70B)
2.b Aromatic/amide H refined with riding coordinates:
 C36(H36), C35(H35), C7(H7), C46(H46), C30(H30), C15(H15), C61(H61), C8(H8),
 C27(H27), C47(H47), C38(H38), C4(H4), C11(H11), C28(H28), C52(H52), C44(H44),
 C5(H5), C14(H14), C45(H45), C18(H18), C62(H62), C59(H59), C39(H39), C19(H19),
 C41(H41), C29(H29), C56(H56), C2(H2), C25(H25), C64(H64), C24(H24), C63(H63),
 C22(H22), C58(H58), C1(H1), C53(H53)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C66(H66A,H66B,H66C), C68(H68A,H68B,H68C), C34(H34A,H34B,
 H34C)
;
_smtbx_masks_void_probe_radius   1.227
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              73579
_shelx_fab_checksum              55680
_olex2_submission_special_instructions 'No special instructions were received'