A chiral BINOL-based supramolecular gel enabling sensitive enantioselective and chemoselective collapse toward histidine.
Jiang, Yixuan; Huang, Zeng; Tian, Jun; Dong, Xin; Yu, Xiao-Qi; Yu, Shanshan; Soft matter 19 (2023) 430–435; doi:10.1039/d2sm01424f

data_1568174
_publ_section_title
;
 A chiral BINOL-based supramolecular gel enabling sensitive
 enantioselective and chemoselective collapse toward histidine.
;
_journal_issue                   3
_journal_name_full               'Soft matter'
_journal_page_first              430
_journal_page_last               435
_journal_paper_doi               10.1039/d2sm01424f
_journal_volume                  19
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H20 O8 P, 0.5(C2 H6 O), 2.5(H2 O)'
_chemical_formula_sum            'C35 H28 O11 P'
_chemical_formula_weight         655.54
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-12 deposited with the CCDC.	2022-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.6884(7)
_cell_length_b                   17.0653(10)
_cell_length_c                   28.5141(13)
_cell_measurement_reflns_used    9163
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      23.892
_cell_measurement_theta_min      2.383
_cell_volume                     6660.8(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      302.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            61453
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         1.907
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1200 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.9276.
The \l/2 correction factor is Not present.
;
_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    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             2728
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     862
_refine_ls_number_reflns         15249
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1117
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0638P)^2^+0.3957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1480
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                9276
_reflns_number_total             15249
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sm01424f2.cif
_cod_data_source_block           mo_yxq_jyx_7_0428_0m_a
_cod_depositor_comments
;
          Adding full bibliography for 1568174.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C70 H56 O22 P2'
_cod_original_formula_weight         1311.08
_cod_original_formula_moiety         '2(C34 H20 O8 P), C2 H6 O, 5(H2 O)'
_cod_original_formula_units_Z            4
_cod_database_code               1568174
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.975
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O024-H02O
 0.85 with sigma of 0.01
 O024-H02N
 0.85 with sigma of 0.01
3. Rigid bond restraints
 O00G, C01W
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O00G \\sim C01W: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
5.a Riding coordinates:
 O00Q(H00A,H00C), O024(H02N,H02O)
5.b Free rotating group:
 O01J(H01C,H01D), O02L(H02P,H02Q), O1(H1A,H1B)
5.c Secondary CH2 refined with riding coordinates:
 C02K(H02B,H02F)
5.d Aromatic/amide H refined with riding coordinates:
 C00U(H00U), C00V(H00V), C00Z(H00Z), C016(H016), C018(H018), C01A(H01A),
 C01B(H01B), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01K(H01K),
 C01M(H01M), C01N(H01N), C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S),
 C01T(H01T), C01V(H01V), C01X(H01X), C01Z(H01Z), C022(H022), C023(H023),
 C025(H025), C026(H026), C028(H028), C029(H029), C02A(H02A), C02C(H02C),
 C02D(H02D), C02E(H02E), C02G(H02G), C02H(H02H), C02I(H02I), C02J(H02J)
5.e Idealised Me refined as rotating group:
 C02N(H02K,H02L,H02M)
5.f Idealised tetrahedral OH refined as rotating group:
 O00B(H00B), O00D(H00D), O00E(H00E), O00G(H00G), O01U(H01U)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              58207
_shelx_hkl_checksum              71855
_shelx_fab_checksum              63890
_olex2_submission_special_instructions 'No special instructions were received'