Simple and visual approach for enantioselective recognition through supramolecular gels with specific selectivity
Xu, Xuemei; Qu, Lang; Song, Jintong; Wu, Dehua; Zhou, Xiangge; Xiang, Haifeng; Chemical Communications  (2019) –; doi:10.1039/C9CC04895B

data_7123910
_publ_section_title
;
 Simple and visual approach for enantioselective recognition through
 supramolecular gels with specific selectivity
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC04895B
_journal_year                    2019
_chemical_formula_moiety         '3(C7 H4.667 O), 3(C0.667 H2 O0.333 S0.333)'
_chemical_formula_sum            'C23 H20 O4 S'
_chemical_formula_weight         392.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-19
_audit_creation_method
;
Olex2 1.3-dev
(compiled 2019.03.18 svn.r3573 for OlexSys, GUI svn.r5830)
;
_audit_update_record
;
2019-07-23 deposited with the CCDC.    2019-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   8.9789(6)
_cell_length_b                   20.4612(11)
_cell_length_c                   32.6305(18)
_cell_measurement_reflns_used    8810
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9030
_cell_measurement_theta_min      3.0980
_cell_volume                     5994.8(6)
_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 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -61.00  -33.70   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  131.0000   -4.0000 39

  2 omega  -64.00  -39.50   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  138.0000  171.0000 35

  3 omega   17.00   42.90   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9200 -138.0000  109.0000 37

  4 omega   13.00   38.90   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9200 -131.0000  -74.0000 37

  5 omega  -62.00  -34.70   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000  120.0000 39

  6 omega  -25.00   24.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000  -60.0000 70

  7 omega  -64.00  -36.70   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000   90.0000 39

  8 omega  -86.00  -44.00   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106 -178.0000 -180.0000 60

  9 omega  -18.00   21.90   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000 -180.0000 57

 10 omega   33.00   60.30   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9200 -178.0000    0.0000 39

 11 omega  -50.00   33.30   0.7000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9200  -57.0000  150.0000 119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            49899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.942
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90910
_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            yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_description       sheet
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       0.0009(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   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     881
_refine_ls_number_reflns         12233
_refine_ls_number_restraints     138
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1429
_refine_ls_R_factor_gt           0.0758
_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^)+(0.0779P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1921
_reflns_Friedel_coverage         0.801
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6450
_reflns_number_total             12233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc04895b2.cif
_cod_data_source_block           190523_s3_xxm
_cod_database_code               7123910
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-S1 \\sim O10A-S1A
 with sigma of 0.02
 C64-S1 \\sim C64A-S1A
 with sigma of 0.02
 C65-S1 \\sim C65A-S1A
 with sigma of 0.02
 O10-C64 \\sim O10A-C64A
 with sigma of 0.04
 O10-C65 \\sim O10A-C65A
 with sigma of 0.04
 C64-C65 \\sim C64A-C65A
 with sigma of 0.04
 O11-C66 \\sim O11A-C66A
 with sigma of 0.04
 O11-C67 \\sim O11A-C67A
 with sigma of 0.04
 O11-S2 \\sim O11A-S2A
 with sigma of 0.04
 C66-C67 \\sim C66A-C67A
 with sigma of 0.04
 C66-S2 \\sim C66A-S2A
 with sigma of 0.04
 C67-S2 \\sim C67A-S2A
 with sigma of 0.04
 O12-C68 \\sim O12A-C68A
 with sigma of 0.04
 O12-C69 \\sim O12A-C69A
 with sigma of 0.04
 O12-S3 \\sim O12A-S3A
 with sigma of 0.04
 C68-C69 \\sim C68A-C69A
 with sigma of 0.04
 C68-S3 \\sim C68A-S3A
 with sigma of 0.04
 C69-S3 \\sim C69A-S3A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C68 \\sim C69A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C68A \\sim C69: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C66A \\sim C67: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
C67A \\sim C66: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
O11A \\sim O11: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002 within 2A
Uanis(O10A) = Uanis(O10)
4. Rigid body (RIGU) restrains
 S1, O10, C64, C65
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S1A, O10A, C64A, C65A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C66, O11, S2, C67
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S2A, O11A, C66A, C67A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O12, S3, C68, C69
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 S3A, O12A, C68A, C69A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(S1A)=Sof(O10A)=Sof(C64A)=Sof(H64D)=Sof(H64E)=Sof(H64F)=Sof(C65A)=
 Sof(H65D)=Sof(H65E)=Sof(H65F)=1-FVAR(1)
 Sof(O10)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=Sof(C65)=Sof(H65A)=Sof(H65B)=
 Sof(H65C)=Sof(S1)=FVAR(1)
 Sof(S2A)=Sof(O11A)=Sof(C66A)=Sof(H66D)=Sof(H66E)=Sof(H66F)=Sof(C67A)=
 Sof(H67D)=Sof(H67E)=Sof(H67F)=1-FVAR(2)
 Sof(O11)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=Sof(C67)=Sof(H67A)=Sof(H67B)=
 Sof(H67C)=Sof(S2)=FVAR(2)
 Sof(S3A)=Sof(O12A)=Sof(C68A)=Sof(H68D)=Sof(H68E)=Sof(H68F)=Sof(C69A)=
 Sof(H69D)=Sof(H69E)=Sof(H69F)=1-FVAR(3)
 Sof(O12)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=Sof(C69)=Sof(H69A)=Sof(H69B)=
 Sof(H69C)=Sof(S3)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C24(H24), C26(H26), C27(H27), C28(H28),
  C29(H29), C32(H32), C35(H35), C36(H36), C38(H38), C39(H39), C40(H40),
 C41(H41), C45(H45), C47(H47), C48(H48), C49(H49), C50(H50), C53(H53), C56(H56),
  C57(H57), C59(H59), C60(H60), C61(H61), C62(H62)
6.b Idealised Me refined as rotating group:
 C64(H64A,H64B,H64C), C65(H65A,H65B,H65C), C66(H66A,H66B,H66C), C67(H67A,H67B,
 H67C), C68(H68A,H68B,H68C), C69(H69A,H69B,H69C), C64A(H64D,H64E,H64F),
 C65A(H65D,H65E,H65F), C66A(H66D,H66E,H66F), C67A(H67D,H67E,H67F), C68A(H68D,
 H68E,H68F), C69A(H69D,H69E,H69F)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4), O6(H6A), O7(H7A), O9(H9)
;
_shelx_res_checksum              14847
_olex2_submission_special_instructions 'No special instructions were received'