Diastereo- and Enantioselective Synthesis of Spirooxindoles with Contiguous Tetrasubstituted Stereocenters via Catalytic Coupling of Two Tertiary Radicals.
Song, Zhi-Yong; Chen, Kun-Quan; Chen, Xiang-Yu; Ye, Song; The Journal of organic chemistry 83 (2018) 2966–2970; doi:10.1021/acs.joc.7b03161

data_4034954
_publ_section_title
;
 Diastereo- and Enantioselective Synthesis of Spirooxindoles with
 Contiguous Tetrasubstituted Stereocenters via Catalytic Coupling of Two
 Tertiary Radicals.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2966
_journal_page_last               2970
_journal_paper_doi               10.1021/acs.joc.7b03161
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H14 Br N O3'
_chemical_formula_sum            'C18 H14 Br N O3'
_chemical_formula_weight         372.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.302(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.351(2)
_cell_length_b                   10.255(3)
_cell_length_c                   18.062(6)
_cell_measurement_reflns_used    4671
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4778
_cell_measurement_theta_min      2.2791
_cell_volume                     1530.6(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution
;
'SHELXT (Sheldrick, 2014)'

;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1082
	          2theta: -19.9473
scan:
	Number of images: 240
	           Slice: -80.0000 - 40.0000
	     Image width: 0.5000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1082
	          2theta: -19.9473
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0022
_diffrn_orient_matrix_UB_12      -0.1091
_diffrn_orient_matrix_UB_13      0.0522
_diffrn_orient_matrix_UB_21      -0.0955
_diffrn_orient_matrix_UB_22      0.0100
_diffrn_orient_matrix_UB_23      0.0169
_diffrn_orient_matrix_UB_31      -0.0113
_diffrn_orient_matrix_UB_32      -0.0305
_diffrn_orient_matrix_UB_33      -0.0455
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9765
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.023
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    2.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.084
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.135
_refine_ls_R_factor_all          0.0542
_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
'w=1/[\s^2^(Fo^2^)+(0.0185P)^2^+2.3829P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3124
_reflns_number_total             3464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03161_si_002.cif
_cod_data_source_block           sa5017
_cod_original_cell_volume        1530.7(8)
_cod_database_code               4034954
_diffrn_number_total             3665
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15), C16(H16), C18(H18)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              66098
_shelx_hkl_checksum              93953
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'