An asymmetric approach toward chiral multicyclic spirooxindoles from isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary amine thiourea catalyst
Qiao Chen; Jinyan Liang; Shoulei Wang; Dong Wang; Rui Wang; Chemical communications (Cambridge, England) 49 (2013) 1657–1659; doi:10.1039/c3cc38386e

data_7108864
_publ_section_title
;
 An asymmetric approach toward chiral multicyclic spirooxindoles from
 isothiocyanato oxindoles and unsaturated pyrazolones by a chiral tertiary
 amine thiourea catalyst
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1657
_journal_page_last               1659
_journal_paper_doi               10.1039/c3cc38386e
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H28 N4 O2 S'
_chemical_formula_sum            'C34 H28 N4 O2 S'
_chemical_formula_weight         556.66
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-10-31
_audit_creation_method
;
Olex2 1.2
(compiled Oct 26 2012 17:06:22, GUI svn.r4371)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0892(3)
_cell_length_b                   18.1126(16)
_cell_length_c                   19.1621(7)
_cell_measurement_reflns_used    2357
_cell_measurement_temperature    293.04(10)
_cell_measurement_theta_max      28.3414
_cell_measurement_theta_min      3.0907
_cell_volume                     2807.6(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXH, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293.04(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9096
_diffrn_measured_fraction_theta_max 0.8777
_diffrn_measurement_details
;
1 omega -87.00 -56.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -19.1930 178.0000 -180.0000 31
2 omega 38.00 92.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 0.0000 120.0000 54
3 omega 23.00 73.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 22.6305 19.0000 -120.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0257554000
_diffrn_orient_matrix_UB_12      -0.0369512000
_diffrn_orient_matrix_UB_13      0.0059153000
_diffrn_orient_matrix_UB_21      -0.0697997000
_diffrn_orient_matrix_UB_22      0.0130840000
_diffrn_orient_matrix_UB_23      0.0186525000
_diffrn_orient_matrix_UB_31      -0.0463641000
_diffrn_orient_matrix_UB_32      0.0008282000
_diffrn_orient_matrix_UB_33      -0.0314160000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6101
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.10
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0347P)^2^+0.2728P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1028
_reflns_number_gt                3747
_reflns_number_total             4415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc38386e.txt
_cod_data_source_block           chenqiao1027
_cod_database_code               7108864
_reflns_odcompleteness_completeness 90.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
H25 of C25, H26 of C26, H30 of C30, H31 of C31, H32 of C32, H33 of C33, H34
of C34, H5 of C5, H4 of C4, H3 of C3, H2 of C2, H9 of C9, {H14A,H14B} of C14,
H16 of C16, H17 of C17, H18 of C18, H19 of C19, H20 of C20, H22 of C22, H23
of C23, H24 of C24
At 1.5 times of:
{H27A,H27B,H27C} of C27, {H28A,H28B,H28C} of C28
2.a Ternary CH refined with riding coordinates:
C9(H9)
2.b Secondary CH2 refined with riding coordinates:
C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19),
C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C30(H30), C31(H31),
C32(H32), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;