Catalytic Enantioselective Ring-Opening and Ring-Closing Reactions of 3-Isothiocyanato Oxindoles and N-(2-Picolinoyl)aziridines.
Wang, Linqing; Yang, Dongxu; Li, Dan; Wang, Rui; Organic letters 17 (2015) 3004–3007; doi:10.1021/acs.orglett.5b01291

data_1520224
_publ_section_title
;
 Catalytic Enantioselective Ring-Opening and Ring-Closing Reactions of
 3-Isothiocyanato Oxindoles and N-(2-Picolinoyl)aziridines.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3004
_journal_page_last               3007
_journal_paper_doi               10.1021/acs.orglett.5b01291
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H22 N4 O2 S'
_chemical_formula_sum            'C22 H22 N4 O2 S'
_chemical_formula_weight         406.50
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 112.70(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.363(3)
_cell_length_b                   9.318(2)
_cell_length_c                   11.453(4)
_cell_measurement_reflns_used    800
_cell_measurement_temperature    291.89(10)
_cell_measurement_theta_max      22.8450
_cell_measurement_theta_min      4.0330
_cell_volume                     1020.3(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.89(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details
;
  1 omega   60.00   91.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946 -178.0000 -120.0000 21

  2 omega   -5.00   92.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946   38.0000   90.0000 65

  3 omega   38.00   83.00   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  178.0000  -60.0000 30

  4 omega  -36.00    4.50   1.5000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.7946  -19.0000  120.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0339506000
_diffrn_orient_matrix_UB_12      -0.0636980000
_diffrn_orient_matrix_UB_13      0.0307273000
_diffrn_orient_matrix_UB_21      -0.0314292000
_diffrn_orient_matrix_UB_22      0.0073956000
_diffrn_orient_matrix_UB_23      0.0446570000
_diffrn_orient_matrix_UB_31      -0.0580201000
_diffrn_orient_matrix_UB_32      -0.0412163000
_diffrn_orient_matrix_UB_33      -0.0395576000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.1015
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4520
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.87
_diffrn_reflns_theta_min         3.62
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark colourless'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1618
_reflns_number_gt                1936
_reflns_number_total             2969
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b01291_si_001.cif
_cod_data_source_block           ydx_1202
_cod_depositor_comments          'Adding full bibliography for 1520224.cif.'
_cod_original_cell_volume        1020.2(5)
_cod_database_code               1520224
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C)
;
_olex2_date_sample_data_collection 2014-12-03
_olex2_submission_special_instructions 'No special instructions were received'