Silver-Catalyzed Tandem Hydroamination/Hydroarylation of 1-(2-Allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-Allylspiro[indene-1,2'-indolin]-3'-ones.
Mothe, Srinivasa Reddy; Novianti, Maria Laurentia; Ayers, Benjamin James; Chan, Philip Wai Hong; Organic letters 16 (2014) 4110–4113; doi:10.1021/ol501809p

data_1517250
_publ_section_title
;
 Silver-Catalyzed Tandem Hydroamination/Hydroarylation of
 1-(2-Allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to
 1'-Allylspiro[indene-1,2'-indolin]-3'-ones.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4110
_journal_page_last               4113
_journal_paper_doi               10.1021/ol501809p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C25 H17 Cl2 N O'
_chemical_formula_sum            'C25 H17 Cl2 N O'
_chemical_formula_weight         418.30
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.272(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8744(2)
_cell_length_b                   14.0493(5)
_cell_length_c                   20.5936(8)
_cell_measurement_reflns_used    6485
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.82
_cell_measurement_theta_min      2.45
_cell_volume                     1988.92(12)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26686
_diffrn_reflns_theta_full        30.50
_diffrn_reflns_theta_max         30.50
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.9471
_exptl_absorpt_correction_T_min  0.8749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.067
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0738P)^2^+0.7024P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1442
_reflns_number_gt                4670
_reflns_number_total             6020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501809p_si_002.cif
_cod_data_source_block           chan194
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1517250.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1517250