Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids, Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes
Nelson, Eryn; Formen, Jeffrey S. S. K.; Wolf, Christian; Chemical Science  (2021) –; doi:10.1039/D1SC02061G

data_1562896
_publ_section_title
;
 Rapid Organocatalytic Chirality Analysis of Amines, Amino Acids,
 Alcohols, Amino Alcohols and Diols with Achiral Iso(thio)cyanate Probes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02061G
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H15 N3 O3'
_chemical_formula_sum            'C15 H15 N3 O3'
_chemical_formula_weight         285.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     intrinsic
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-04-13 deposited with the CCDC.	2021-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.422(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.64130(10)
_cell_length_b                   11.0456(3)
_cell_length_c                   13.6158(4)
_cell_measurement_reflns_used    5088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.12
_cell_measurement_theta_min      3.27
_cell_volume                     693.65(3)
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_collection       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_data_reduction
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from \f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9430
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.334
_diffrn_reflns_theta_min         3.266
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  0.97629
_exptl_absorpt_correction_T_min  0.73996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_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     197
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0882P)^2^+0.0660P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1272
_reflns_Friedel_coverage         0.878
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2409
_reflns_number_total             2503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02061g2.cif
_cod_data_source_block           20100_a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1562896
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.676
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              63781
_shelx_hkl_checksum              19124