Lanthanide amide-catalyzed one-pot functionalization of isatins: synthesis of spiro[cyclopropan-1,3′-oxindoles] and 2-oxoindolin-3-yl phosphates
Peng, Cheng; Zhai, Jiaojiao; Xue, Mingqiang; Xu, Fan; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB00640C

data_7155585
_publ_section_title
;
 Lanthanide amide-catalyzed one-pot functionalization of isatins:
 synthesis of spiro[cyclopropan-1,3&#x2032;-oxindoles] and
 2-oxoindolin-3-yl phosphates
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB00640C
_journal_year                    2017
_chemical_formula_moiety         'C15 H14 Br N O3'
_chemical_formula_sum            'C15 H14 Br N O3'
_chemical_formula_weight         336.18
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-07-15 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.508(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.1366(8)
_cell_length_b                   13.6377(10)
_cell_length_c                   10.5947(8)
_cell_measurement_reflns_used    6614
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.50
_cell_measurement_theta_min      2.45
_cell_volume                     1452.05(19)
_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      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0815
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24186
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_T_max  0.6005
_exptl_absorpt_correction_T_min  0.4280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0395P)^2^+1.0065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1243
_reflns_number_gt                2620
_reflns_number_total             4250
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob00640c2.cif
_cod_data_source_block           b141218a_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7155585