Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes: facile access to spiro 3,3'-cyclopropyl oxindoles.
Ladd, Carolyn L.; Sustac Roman, Daniela; Charette, André B.; Organic letters 15 (2013) 1350–1353; doi:10.1021/ol4003338

data_1511884
_publ_section_title
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 Silver-promoted, palladium-catalyzed direct arylation of cyclopropanes:
 facile access to spiro 3,3'-cyclopropyl oxindoles.
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_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1350
_journal_page_last               1353
_journal_paper_doi               10.1021/ol4003338
_journal_volume                  15
_journal_year                    2013
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C17 H14 Cl N O'
_chemical_formula_sum            'C17 H14 Cl N O'
_chemical_formula_weight         283.74
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5875(8)
_cell_length_b                   17.8684(12)
_cell_length_c                   6.0173(4)
_cell_measurement_reflns_used    37521
_cell_measurement_temperature    150
_cell_measurement_theta_max      69.35
_cell_measurement_theta_min      3.51
_cell_volume                     1353.40(15)
_computing_cell_refinement       'SAINT V7.68A(Bruker AXS, 2009)'
_computing_data_collection       'APEX2  (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A(Bruker AXS, 2009)'
_computing_molecular_graphics    'SHELXTL  (Bruker AXS, 2003)'
_computing_publication_material  'UdMX (Maris, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.039
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            39869
_diffrn_reflns_theta_full        69.70
_diffrn_reflns_theta_max         69.70
_diffrn_reflns_theta_min         4.30
_exptl_absorpt_coefficient_mu    2.440
_exptl_absorpt_correction_T_max  0.6935
_exptl_absorpt_correction_T_min  0.5640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
'Flack, H.D. and Schwarzenbach, D. (1999), 556 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.127(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         1968
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0299
_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^)+(0.0577P)^2^+0.2414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0791
_reflns_number_gt                1968
_reflns_number_total             1968
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ol4003338_si_002.cif
_cod_data_source_block           cha217
_cod_depositor_comments
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The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
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_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               1511884