Double C-H Activation during Functionalization of Phenyl(methyl)ketene on Iridium(I) Using Alkynes. Synthesis of 1,4-Dien-3-ones
Douglas B. Grotjahn; Justin M. Hoerter; John L. Hubbard; Journal of the American Chemical Society 126 (2004) 8866–8867; doi:10.1021/ja048489+

data_4112783
_publ_section_title
;
 Double C-H Activation during Functionalization of Phenyl(methyl)ketene on
 Iridium(I) Using Alkynes. Synthesis of 1,4-Dien-3-ones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8866
_journal_page_last               8867
_journal_paper_doi               10.1021/ja048489+
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        'Grotjahn Lab'
_chemical_formula_moiety         'C31 H56 Cl Ir O P2'
_chemical_formula_sum            'C31 H56 Cl Ir O P2'
_chemical_formula_weight         739.2
_chemical_name_common            'Ir-metallacycle complex'
_chemical_name_systematic
; 
 ? 
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.540(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0280(10)
_cell_length_b                   15.732(2)
_cell_length_c                   21.362(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      1.5
_cell_volume                     3332.7(6)
_computing_cell_refinement       P3
_computing_data_collection       P3
_computing_data_reduction        P3
_computing_molecular_graphics    XP
_computing_publication_material  SHELX
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'theta-2 theta'
_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  0.1140
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6321
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        '< 1%'
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    4.203
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
 An empirical absorption correction (ellipsoid model) was applied by collecting 
 psi scans (5 high chi reflections) and using the XEMP program supplied by 
 Siemens. The T(max)/T(min) ratio is a little high (1.3) but was deemed to be 
 the best model possible.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         1.839
_refine_diff_density_min         -1.560
_refine_diff_density_rms         0.183
_refine_ls_extinction_coef       0.00123(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.076
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.048
_refine_ls_restrained_S_obs      1.049
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+20.0628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2190
_refine_ls_wR_factor_ref         0.0975
_reflns_number_gt                4395
_reflns_number_total             5887
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0484892Bsi20040528_015436.cif
_cod_data_source_block           dg22d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' 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/n'
_cod_database_code               4112783