Solvent selection as a major determinant of chiral resolution outcomes: The BINOL-DACH case study
de Meester, Joséphine; Shemchuk, Oleksii; Collard, Laurent; Wouters, Johan; Robeyns, Koen; Leyssens, Tom; CrystEngComm  (2025) –; doi:10.1039/D5CE00706B

data_7251200
_publ_section_title
;
 Solvent selection as a major determinant of chiral resolution outcomes:
 The BINOL-DACH case study
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00706B
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         '4(C20 H13 O2), 4(C6 H15 N2), 3(C2 H6 O), H2 O'
_chemical_formula_sum            'C110 H132 N8 O12'
_chemical_formula_weight         1758.23
_chemical_name_common            'BINOL +  DACH'
_chemical_name_systematic
'1,1'-bi-2-naphtol + trans-cyclohexane-1,2-diamine'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-07-06 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                87.176(7)
_cell_angle_beta                 89.274(8)
_cell_angle_gamma                76.533(8)
_cell_formula_units_Z            1
_cell_length_a                   10.3936(12)
_cell_length_b                   11.2508(9)
_cell_length_c                   20.951(2)
_cell_measurement_reflns_used    4597
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.3920
_cell_measurement_theta_min      2.9000
_cell_volume                     2379.7(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method
;
'120 images, \D\F 2.0\% '
'120 images, \D\F 2.0\% (2nd orientation)'
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            41911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_min         2.561
_diffrn_source                   'Incoatec microfocus source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94435
_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    1.227
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 3762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1227
_refine_ls_number_reflns         17196
_refine_ls_number_restraints     1172
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0680
_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^)+(0.0856P)^2^+0.7211P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.1907
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                10464
_reflns_number_total             17196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00706b2.cif
_cod_data_source_block           jdm_rBIN_RRDACHEtOH
_cod_original_cell_volume        2379.6(4)
_cod_database_code               7251200
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              33779