Asymmetric Synthesis of Spiro[isoxazolin-3,3'-oxindoles] via the Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides.
Lian, Xiangjin; Guo, Songsong; Wang, Gang; Lin, Lili; Liu, Xiaohua; Feng, Xiaoming; The Journal of organic chemistry 79 (2014) 7703–7710; doi:10.1021/jo5012625

data_4029904
_publ_section_title
;
 Asymmetric Synthesis of Spiro[isoxazolin-3,3'-oxindoles] via the
 Catalytic 1,3-Dipolar Cycloaddition Reaction of Nitrile Oxides.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7703
_journal_page_last               7710
_journal_paper_doi               10.1021/jo5012625
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C27 H23 Br N2 O4'
_chemical_formula_sum            'C27 H23 Br N2 O4'
_chemical_formula_weight         519.38
_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
_audit_creation_date             2013-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8655(3)
_cell_length_b                   17.0671(4)
_cell_length_c                   17.9180(6)
_cell_measurement_reflns_used    2110
_cell_measurement_temperature    143.2(5)
_cell_measurement_theta_max      25.3500
_cell_measurement_theta_min      3.4400
_cell_volume                     2405.34(13)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      143.2(5)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.7604
_diffrn_measurement_details
;
  1 omega  -87.00  -53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5174 -178.0000   90.0000 34

  2 omega  -45.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       19.2361  -19.0000 -120.0000 106
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0319898000
_diffrn_orient_matrix_UB_12      0.0214240000
_diffrn_orient_matrix_UB_13      0.0309165000
_diffrn_orient_matrix_UB_21      -0.0795896000
_diffrn_orient_matrix_UB_22      -0.0191278000
_diffrn_orient_matrix_UB_23      -0.0038497000
_diffrn_orient_matrix_UB_31      0.0279408000
_diffrn_orient_matrix_UB_32      -0.0300368000
_diffrn_orient_matrix_UB_33      0.0243982000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6535
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.070
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57851
_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
;
;
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.004(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0411
_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^)+(0.0245P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0797
_reflns_Friedel_coverage         0.588
_reflns_Friedel_fraction_full    0.821
_reflns_Friedel_fraction_max     0.776
_reflns_number_gt                3734
_reflns_number_total             4439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5012625_si_002.cif
_cod_data_source_block           131118_s1_lxj
_cod_database_code               4029904
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o3br1
_shelx_estimated_absorpt_t_max   0.722
_shelx_estimated_absorpt_t_min   0.623
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              21885
_shelx_hkl_checksum              12103