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_7133092
_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_absolute_configuration rm
_chemical_formula_moiety         '2(C20 H14 O2), C5 H9 N O2'
_chemical_formula_sum            'C45 H37 N O6'
_chemical_formula_weight         687.75
_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   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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.12901(14)
_cell_length_b                   13.7793(2)
_cell_length_c                   27.6456(4)
_cell_measurement_reflns_used    22668
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.9920
_cell_measurement_theta_min      2.9430
_cell_volume                     3477.58(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       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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'90 images, \D\F 3.0\% '
'49 images, \D\F 3.0\% (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            49534
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.033
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94403
_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            volourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: cooling from ethanol solution'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 2691 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.29(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     668
_refine_ls_number_reflns         6821
_refine_ls_number_restraints     254
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0306P)^2^+0.9988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                6484
_reflns_number_total             6821
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02180k2.cif
_cod_data_source_block           alex_RSBin_DLpro
_cod_depositor_comments
'Adding full bibliography for 7133091--7133092.cif.'
_cod_database_code               7133092
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              73630
_shelx_hkl_checksum              23228