Synthesis of chiral cyclohexanol derived benzylamines, applications for enantiodiscrimination of optically active analytes by NMR spectroscopy
Parmar, Binal B.; Abraham, Alex; Butcher, Raymond J.; Bedekar, Ashutosh; New Journal of Chemistry  (2026) –; doi:10.1039/D5NJ02505B

data_7064148
_publ_section_title
;
 Synthesis of chiral cyclohexanol derived benzylamines, applications for
 enantiodiscrimination of optically active analytes by NMR spectroscopy
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/D5NJ02505B
_journal_year                    2026
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C21 H28 N O2), C4 H4 O6'
_chemical_formula_sum            'C46 H60 N2 O10'
_chemical_formula_weight         800.96
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-04-30 deposited with the CCDC.	2025-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   10.99230(10)
_cell_length_b                   10.99230(10)
_cell_length_c                   61.8008(6)
_cell_measurement_reflns_used    35297
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      75.9770
_cell_measurement_theta_min      2.8640
_cell_volume                     6466.99(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       77
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            83354
_diffrn_reflns_point_group_measured_fraction_full 0.863
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.358
_diffrn_reflns_theta_min         2.860
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74160
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       prism
_exptl_crystal_F_000             2580
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.481
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2451 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     768
_refine_ls_number_reflns         7605
_refine_ls_number_restraints     1130
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0559
_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^)+(0.1195P)^2^+0.7892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1771
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.724
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                6991
_reflns_number_total             7605
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02505b2.cif
_cod_data_source_block           bp-b10
_cod_original_cell_volume        6466.98(13)
_cod_database_code               7064148
_shelx_shelxl_version_number     2019/3
_shelx_res_checksum              50293