Facile synthesis of aza-spirocyclopropanyl oxindoles by the reaction of 3-(2-bromoethyl)-indole with 2,3-dimethylimidazole-1-sulfonyl azide triflate.
Shen, Mei-Hua; Xu, Ke; Sun, Chu-Han; Xu, Hua-Dong; Organic & biomolecular chemistry 14 (2016) 1272–1276; doi:10.1039/c5ob02192h

data_7154822
_publ_section_title
;
 Facile synthesis of aza-spirocyclopropanyl oxindoles by the reaction of
 3-(2-bromoethyl)-indole with 2,3-dimethylimidazole-1-sulfonyl azide
 triflate.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1272
_journal_page_last               1276
_journal_paper_doi               10.1039/c5ob02192h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_sum            'C12 H14 N2 O3 S'
_chemical_formula_weight         266.31
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-17 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                79.307(3)
_cell_angle_beta                 84.564(3)
_cell_angle_gamma                79.146(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3507(13)
_cell_length_b                   8.6494(14)
_cell_length_c                   9.0014(15)
_cell_measurement_reflns_used    3429
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.28
_cell_measurement_theta_min      2.31
_cell_volume                     626.23(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3408
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  0.9522
_exptl_absorpt_correction_T_min  0.9330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.124(17)
_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   1.113
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2165
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0891P)^2^+0.2763P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1468
_reflns_number_gt                2018
_reflns_number_total             2165
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob02192h2.cif
_cod_data_source_block           mo_150128j_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7154822.cif.
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7154822