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_7122896
_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            S-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_block_doi                 10.5517/ccdc.csd.cc20jxdw
_audit_creation_date             2019-01-16
_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                110.603(4)
_cell_angle_beta                 90.185(4)
_cell_angle_gamma                92.969(4)
_cell_formula_units_Z            1
_cell_length_a                   10.1547(5)
_cell_length_b                   12.0754(5)
_cell_length_c                   15.9307(6)
_cell_measurement_reflns_used    7909
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.4360
_cell_measurement_theta_min      3.9820
_cell_volume                     1825.58(14)
_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 5.2371
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
  1 omega  -48.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3797   37.0000   60.0000 78

  2 omega    6.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3797  -99.0000  120.0000 59

  3 omega   52.00  122.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446 -125.0000    0.0000 70

  4 omega   49.00   87.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -30.0000  -60.0000 38

  5 omega   45.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -30.0000 -150.0000 46

  6 omega   76.00  178.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446   30.0000 -120.0000 102

  7 omega  151.00  178.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  125.0000    0.0000 27

  8 omega  127.00  178.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446   30.0000  150.0000 51

  9 omega   79.00  115.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446   30.0000  150.0000 36

 10 omega   39.00  134.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -61.0000  150.0000 95

 11 omega   46.00  105.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -94.0000   30.0000 59

 12 omega   33.00   88.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -30.0000   90.0000 55

 13 omega   27.00   99.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -94.0000  120.0000 72

 14 omega   26.00   78.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  -30.0000  -90.0000 52

 15 omega  109.00  151.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      103.3446  125.0000 -180.0000 42

 16 omega  -42.00   24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3797   37.0000 -150.0000 66

 17 omega  -86.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3797  125.0000 -120.0000 78

 18 omega -114.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3797  -37.0000 -120.0000 100
;
_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      0.0681035000
_diffrn_orient_matrix_UB_12      0.1059410000
_diffrn_orient_matrix_UB_13      0.0751544000
_diffrn_orient_matrix_UB_21      0.0080873000
_diffrn_orient_matrix_UB_22      0.0709417000
_diffrn_orient_matrix_UB_23      -0.0636491000
_diffrn_orient_matrix_UB_31      -0.1355994000
_diffrn_orient_matrix_UB_32      0.0487857000
_diffrn_orient_matrix_UB_33      0.0312896000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11834
_diffrn_reflns_point_group_measured_fraction_full 0.582
_diffrn_reflns_point_group_measured_fraction_max 0.560
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.696
_diffrn_reflns_theta_min         3.917
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.937
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68965
_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    1.242
_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         1.308
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.035(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     851
_refine_ls_number_reflns         8001
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+6.0453P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.172
_reflns_Friedel_fraction_full    0.175
_reflns_Friedel_fraction_max     0.164
_reflns_number_gt                7918
_reflns_number_total             8001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08947g2.cif
_cod_data_source_block           S-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               7122896
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.758
_shelx_estimated_absorpt_t_min   0.758
_reflns_odcompleteness_completeness 99.82
_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. Rigid bond restraints
 C13, C12, C9, C10, C15, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C12 \\sim C13 \\sim C14 \\sim C15 \\sim C10 \\sim C9: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
4.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C72(H72A,H72B), C70(H70A,H70B), C33(H33A,H33B), C67(H67A,
 H67B), C66(H66A,H66B), C69(H69A,H69B), C68(H68A,H68B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C49(H49), C36(H36), C7(H7), C27(H27), C4(H4), C1(H1), C48(H48),
 C63(H63), C42(H42), C8(H8), C41(H41), C52(H52), C11(H11), C62(H62), C30(H30),
 C29(H29), C5(H5), C15(H15), C14(H14), C45(H45), C35(H35), C65(H65), C20(H20),
 C19(H19), C38(H38), C57(H57), C25(H25), C60(H60), C22(H22), C39(H39), C64(H64),
  C28(H28), C23(H23), C59(H59), C53(H53)
4.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C71(H71A,H71B,H71C), C56(H56A,H56B,H56C), C34(H34A,H34B,
 H34C)
;
_shelx_res_checksum              78780
_shelx_fab_checksum              84703
_olex2_submission_special_instructions 'No special instructions were received'