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_7155586
_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 Cl N O3'
_chemical_formula_sum            'C15 H14 Cl N O3'
_chemical_formula_weight         291.72
_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
;
2016-07-16 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                88.096(2)
_cell_angle_beta                 71.104(2)
_cell_angle_gamma                72.794(2)
_cell_formula_units_Z            4
_cell_length_a                   10.8908(4)
_cell_length_b                   11.0249(4)
_cell_length_c                   13.2194(5)
_cell_measurement_reflns_used    8085
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.46
_cell_measurement_theta_min      2.37
_cell_volume                     1431.06(9)
_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      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0799
_diffrn_reflns_av_sigmaI/netI    0.0707
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            37254
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_correction_T_min  0.9374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0342P)^2^+0.5836P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                4222
_reflns_number_total             6586
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ob00640c2.cif
_cod_data_source_block           b140420a_0m
_cod_original_cell_volume        1431.07(9)
_cod_database_code               7155586