Synthesis and Reactivity of Ortho-Palladated 3-Phenylpropanamides. Insertion of CO, XyNC, and Alkynes into the Pd–C Bond. Synthesis of Seven- and Nine-Membered Palladacycles and Benzazepine- and Benzazonine-Based Heterocycles
Frutos-Pedreño, Roberto; González-Herrero, Pablo; Vicente, José; Jones, Peter G.; Organometallics 32 (2013) 1892–; doi:10.1021/om4000192

data_4080477
_publ_section_title
;
 Synthesis and Reactivity of Ortho-Palladated 3-Phenylpropanamides.
 Insertion of CO, XyNC, and Alkynes into the Pd--C Bond. Synthesis of
 Seven- and Nine-Membered Palladacycles and Benzazepine- and
 Benzazonine-Based Heterocycles
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1892
_journal_paper_doi               10.1021/om4000192
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C18 H18 N2 O'
_chemical_formula_weight         278.34
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 91.508(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4029(2)
_cell_length_b                   15.6438(4)
_cell_length_c                   20.8748(5)
_cell_measurement_reflns_used    12808
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7914
_cell_measurement_theta_min      2.3425
_cell_volume                     3069.56(13)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) 
(compiled Oct 25 2010,18:11:34) 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) 
(compiled Oct 25 2010,18:11:34) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) 
(compiled Oct 25 2010,18:11:34) 
;
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            50729
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.79
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    'NH free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     781
_refine_ls_number_reflns         9202
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.6097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                7437
_reflns_number_total             9202
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4000192_si_002.cif
_cod_data_source_block           murnit
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4080477