Coupling and Cyclization of o-Iodoanilines and Propargylic Bromides via Allenes: An Efficient Entry to Indomethacin.
Zhu, Can; Ma, Shengming; Organic letters 15 (2013) 2782–2785; doi:10.1021/ol401115a

data_1512097
_publ_section_title
;
 Coupling and Cyclization of o-Iodoanilines and Propargylic Bromides via
 Allenes: An Efficient Entry to Indomethacin.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              2782
_journal_page_last               2785
_journal_paper_doi               10.1021/ol401115a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C19 H19 N O2 S'
_chemical_formula_weight         325.41
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                101.582(2)
_cell_angle_beta                 92.848(2)
_cell_angle_gamma                103.302(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1257(10)
_cell_length_b                   9.1641(10)
_cell_length_c                   10.7395(12)
_cell_measurement_reflns_used    2145
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.884
_cell_measurement_theta_min      5.396
_cell_volume                     851.90(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5173
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72885
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     41
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0540
_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^)+(0.0917P)^2^+0.1727P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1652
_reflns_number_gt                2655
_reflns_number_total             3337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol401115a_si_002.cif
_cod_data_source_block           cd212666
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.3.1 from 2005-06-27.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1512097