Simultaneously resolving BINOL and proline using a stoichiometric cocrystal switch.
Songsermsawad, Sarita; Shemchuk, Oleksii; Robeyns, Koen; Collard, Laurent; E Flood, Adrian; Leyssens, Tom; Chemical communications (Cambridge, England) 60 (2024) 6607–6610; doi:10.1039/d4cc02180k

data_7133091
_publ_section_title
;
 Simultaneously resolving BINOL and proline using a stoichiometric
 cocrystal switch.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6607
_journal_page_last               6610
_journal_paper_doi               10.1039/d4cc02180k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C20 H14 O2, 2(C5 H9 N O2)'
_chemical_formula_sum            'C30 H32 N2 O6'
_chemical_formula_weight         516.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-05-03 deposited with the CCDC.	2024-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                109.33(2)
_cell_angle_beta                 91.872(12)
_cell_angle_gamma                104.146(13)
_cell_formula_units_Z            2
_cell_length_a                   10.4050(9)
_cell_length_b                   10.991(2)
_cell_length_c                   12.216(3)
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      24.9760
_cell_measurement_theta_min      3.1020
_cell_volume                     1268.4(4)
_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       MAR
_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    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'60 images, \D\F 3.0\% '
'53 images, \D\F 3.0\% (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_min         3.143
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87597
_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            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plate
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: cooling from ethanol solution'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         4586
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0781
_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^)+(0.0450P)^2^+0.6186P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2896
_reflns_number_total             4586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02180k2.cif
_cod_data_source_block           alex_2BINOL-PRO
_cod_depositor_comments
'Adding full bibliography for 7133091--7133092.cif.'
_cod_original_cell_volume        1268.4(5)
_cod_database_code               7133091
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              22328
_shelx_hkl_checksum              43260