Asymmetric catalytic 1,3-dipolar cycloaddition reaction of nitrile imines for the synthesis of chiral spiro-pyrazoline-oxindoles.
Wang, Gang; Liu, Xiaohua; Huang, Tianyu; Kuang, Yulong; Lin, Lili; Feng, Xiaoming; Organic letters 15 (2013) 76–79; doi:10.1021/ol303097j

data_1508848
_publ_section_title
;
 Asymmetric catalytic 1,3-dipolar cycloaddition reaction of nitrile imines
 for the synthesis of chiral spiro-pyrazoline-oxindoles.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              76
_journal_page_last               79
_journal_paper_doi               10.1021/ol303097j
_journal_volume                  15
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C33 H29 N3 O3'
_chemical_formula_sum            'C33 H29 N3 O3'
_chemical_formula_weight         515.59
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.777(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0160(12)
_cell_length_b                   18.7857(19)
_cell_length_c                   12.3390(12)
_cell_measurement_reflns_used    30287
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.26
_cell_measurement_theta_min      3.67
_cell_volume                     2759.7(5)
_computing_cell_refinement       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_collection       'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_data_reduction        'Rapid Auto Ver 2.30(Rigaku 1998)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            31266
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.62
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  0.7402
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi March, 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.50
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.07(18)
_refine_ls_extinction_coef       0.00754(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     710
_refine_ls_number_reflns         9346
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0236P)^2^+1.2320P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                8907
_reflns_number_total             9346
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol303097j_si_002.cif
_cod_data_source_block           sx2943
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1508848