Remote activation of the nucleophilicity of isatin.
Zari, Sergei; Kudrjashova, Marina; Pehk, Tõnis; Lopp, Margus; Kanger, Tõnis; Organic letters 16 (2014) 1740–1743; doi:10.1021/ol500421k

data_1513931
_publ_section_title
;
 Remote activation of the nucleophilicity of isatin.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1740
_journal_page_last               1743
_journal_paper_doi               10.1021/ol500421k
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H14 Cl N O5'
_chemical_formula_sum            'C19 H14 Cl N O5'
_chemical_formula_weight         371.76
_chemical_melting_point          422
_chemical_name_systematic
'methyl 3-(p-chlorobenzoyl)-2-(2,3-dioxo-1H-indol-1-yl)propionate'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2013-12-09 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0659(7)
_cell_length_b                   8.7522(9)
_cell_length_c                   23.942(3)
_cell_measurement_reflns_used    5581
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.3452
_cell_measurement_theta_min      2.4777
_cell_volume                     1690.2(3)
_computing_molecular_graphics    'Jmol (Jmol.org, 2008)'
_computing_publication_material  'APEX2 (Bruker, 2011)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            18501
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.478
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.9503
_exptl_absorpt_correction_T_min  0.6013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. University of G\"ottingen, Germany.'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.08(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0383
_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^)+(0.0466P)^2^+0.2903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2642
_reflns_number_total             2992
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol500421k_si_002.cif
_cod_data_source_block           KI13
_cod_database_code               1513931
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.950
_shelxl_version_number           2013-4
_shelx_res_checksum              638
_shelx_hkl_checksum              17021