Enantioselective reaction of N-cyano imines: decarboxylative Mannich-type reaction with malonic acid half thioesters
Oyamada, Yusuke; Inaba, Kazuto; Sasamori, Takahiro; Nakamura, Shuichi; Chemical Communications  (2022) –; doi:10.1039/D1CC07191B

data_7129601
_publ_section_title
;
 Enantioselective reaction of N-cyano imines: decarboxylative Mannich-type
 reaction with malonic acid half thioesters
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07191B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H13 Br N2 O S'
_chemical_formula_sum            'C16 H13 Br N2 O S'
_chemical_formula_weight         361.25
_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
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-01-08 deposited with the CCDC.	2022-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1214(2)
_cell_length_b                   7.30260(10)
_cell_length_c                   19.6104(4)
_cell_measurement_reflns_used    24339
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.7980
_cell_measurement_theta_min      2.1690
_cell_volume                     1531.40(5)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrystalClear
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics
'Yadokari-XG 2011 (Wakita Nemoto et al., 2011)'
_computing_publication_material
'Yadokari-XG 2011 (Wakita,Nemoto et al., 2011)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Rigaku VariMax Saturn'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35795
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.621
_diffrn_reflns_theta_min         2.434
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.820
_exptl_absorpt_correction_T_max  0.827
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 3216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         8896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0485P)^2^+0.3389P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.821
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                7979
_reflns_number_total             8896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc07191b2.cif
_cod_data_source_block           DCM1b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129601
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.766
_shelx_estimated_absorpt_t_max   0.827
_oxdiff_exptl_absorpt_empirical_full_min 0.748
_oxdiff_exptl_absorpt_empirical_full_max 1.282
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_shelx_res_checksum              76880