Catalytic Asymmetric [3 + 2] Cyclization Reactions of 3-Isothiocyanato Oxindoles and Alkynyl Ketones Via an in Situ Generated Magnesium Catalyst.
Wang, Linqing; Yang, Dongxu; Li, Dan; Liu, Xihong; Zhao, Qian; Zhu, Ranran; Zhang, Bangzhi; Wang, Rui; Organic letters 17 (2015) 4260–4263; doi:10.1021/acs.orglett.5b02052

data_1555226
_publ_section_title
;
 Catalytic Asymmetric [3 + 2] Cyclization Reactions of 3-Isothiocyanato
 Oxindoles and Alkynyl Ketones Via an in Situ Generated Magnesium
 Catalyst.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4260
_journal_page_last               4263
_journal_paper_doi               10.1021/acs.orglett.5b02052
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H18 N2 O2 S, C3 H6 O'
_chemical_formula_sum            'C28 H24 N2 O3 S'
_chemical_formula_weight         468.55
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9629(4)
_cell_length_b                   14.1297(8)
_cell_length_c                   18.6198(9)
_cell_measurement_reflns_used    1806
_cell_measurement_temperature    295.42(10)
_cell_measurement_theta_max      27.9230
_cell_measurement_theta_min      3.5840
_cell_volume                     2358.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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_environment      air
_diffrn_ambient_temperature      295.42(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega   48.00   90.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  178.0000  -30.0000 28

  2 omega    1.00   28.00   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854   57.0000    0.0000 18

  3 omega  -27.00   46.50   1.5000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -38.0000  -30.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0545419000
_diffrn_orient_matrix_UB_12      0.0223417000
_diffrn_orient_matrix_UB_13      -0.0217510000
_diffrn_orient_matrix_UB_21      -0.0122002000
_diffrn_orient_matrix_UB_22      0.0341590000
_diffrn_orient_matrix_UB_23      0.0273151000
_diffrn_orient_matrix_UB_31      0.0560391000
_diffrn_orient_matrix_UB_32      0.0292242000
_diffrn_orient_matrix_UB_33      -0.0152172000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6049
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.47
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86527
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0459
_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^)+(0.0309P)^2^+0.1079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                3503
_reflns_number_total             4144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02052_si_001.cif
_cod_data_source_block           wanglq_nq
_cod_database_code               1555226
_reflns_odcompleteness_completeness 99.49
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2a), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C26(H26a,H26b,H26c), C28(H28a,H28b,H28c)
;
_olex2_date_sample_data_collection 2015-04-21
_olex2_submission_special_instructions 'No special instructions were received'