Enantioselective synthesis of pyrazolone α-aminonitrile derivatives via an organocatalytic Strecker reaction
Enders, Dieter; Mahajan, Suruchi; Chauhan, Pankaj; Kaya, Uğur; Deckers, Kristina; Rissanen, Kari; Chem. Commun.  (2017) –; doi:10.1039/C7CC02874A

data_7120210
_publ_section_title
;
 Enantioselective synthesis of pyrazolone \a-aminonitrile derivatives via
 an organocatalytic Strecker reaction
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC02874A
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H13 Cl N4 O'
_chemical_formula_sum            'C17 H13 Cl N4 O'
_chemical_formula_weight         324.76
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3'
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-04 deposited with the CCDC.
2017-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   19.5452(2)
_cell_length_b                   19.5452(2)
_cell_length_c                   10.90990(10)
_cell_measurement_reflns_used    15227
_cell_measurement_temperature    173.0(1)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      0.40
_cell_volume                     3609.37(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.0(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker-Nonius Kappa-ApexII'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37680
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.827
_diffrn_reflns_theta_min         2.221
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0752 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.9133.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       Block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 2164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         5000
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0338P)^2^+0.8729P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0686
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4676
_reflns_number_total             5000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc02874a2.cif
_cod_data_source_block           3g
_cod_original_cell_volume        3609.37(8)
_cod_database_code               7120210
_shelx_shelxl_version_number     2016/4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00N(H00A,H00C,H00E)
;
_shelx_res_checksum              3462
_olex2_submission_special_instructions 'No special instructions were received'