Dihydroperimidine-Derived N-Heterocyclic Pincer Carbene Complexes via Double C‒H Activation
Hill, Anthony F.; McQueen, Caitlin M. A.; Organometallics 31 (2012) 8051–; doi:10.1021/om300897w

data_4079632
_publ_section_title
;
 Dihydroperimidine-Derived N-Heterocyclic Pincer Carbene Complexes via
 Double C--H Activation
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              8051
_journal_paper_doi               10.1021/om300897w
_journal_volume                  31
_journal_year                    2012
_chemical_compound_source        local
_chemical_formula_moiety         'C38 H56 Cl1 Ir1 N2 O1 P2, C4 H8 O1'
_chemical_formula_sum            'C42 H64 Cl Ir N2 O2 P2'
_chemical_formula_weight         918.60
_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   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 108.3841(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3069(3)
_cell_length_b                   13.9062(4)
_cell_length_c                   21.5639(6)
_cell_measurement_reflns_used    23487
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.55
_cell_volume                     4355.8(2)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows v. 2.01'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.118
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7696
_diffrn_reflns_theta_full        25.030
_diffrn_reflns_theta_max         25.030
_diffrn_reflns_theta_min         2.805
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.235
_exptl_absorpt_correction_T_max  0.804
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_platon_squeeze_details
;
;
_refine_diff_density_max         2.36
_refine_diff_density_min         -1.86
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9288
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.0005568
_refine_ls_shift/su_mean         0.0000192
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 6.21P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0831
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0831
_reflns_limit_h_max              17
_reflns_limit_h_min              -18
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                5573
_reflns_number_total             7696
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.02
_oxford_diffrn_Wilson_scale      563.62
_oxford_refine_ls_r_factor_ref   0.0664
_oxford_refine_ls_scale          0.056180(6)
_oxford_reflns_number_all        7695
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            om300897w_si_005.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

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

'_atom_sites_solution_primary' value 'Direct' changed to
'direct' 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 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C42 H64 Cl1 Ir1 N2 O2 P2'
_cod_database_code               4079632
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE IR  (   1,X'S) H   (   1,X'S) 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) H   ( 322,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) H   ( 332,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) H   ( 342,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) H   ( 352,X'S) 
RIDE C   (  36,X'S) H   ( 361,X'S) H   ( 362,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) 
RIDE C   (  42,X'S) H   ( 421,X'S) H   ( 422,X'S) 
RIDE C   (  43,X'S) H   ( 431,X'S) H   ( 432,X'S) 
RIDE C   (  44,X'S) H   ( 441,X'S) H   ( 442,X'S) 
RIDE C   (  45,X'S) H   ( 451,X'S) H   ( 452,X'S) 
RIDE C   (  46,X'S) H   ( 461,X'S) H   ( 462,X'S) 
RIDE C   (  51,X'S) H   ( 511,X'S) 
RIDE C   (  52,X'S) H   ( 521,X'S) H   ( 522,X'S) 
RIDE C   (  53,X'S) H   ( 531,X'S) H   ( 532,X'S) 
RIDE C   (  54,X'S) H   ( 541,X'S) H   ( 542,X'S) 
RIDE C   (  55,X'S) H   ( 551,X'S) H   ( 552,X'S) 
RIDE C   (  56,X'S) H   ( 561,X'S) H   ( 562,X'S) 
RIDE C   (  61,X'S) H   ( 611,X'S) 
RIDE C   (  62,X'S) H   ( 621,X'S) H   ( 622,X'S) 
RIDE C   (  63,X'S) H   ( 631,X'S) H   ( 632,X'S) 
RIDE C   (  64,X'S) H   ( 641,X'S) H   ( 642,X'S) 
RIDE C   (  65,X'S) H   ( 651,X'S) H   ( 652,X'S) 
RIDE C   (  66,X'S) H   ( 661,X'S) H   ( 662,X'S) 
RIDE C   (  72,X'S) H   ( 721,X'S) H   ( 722,X'S) 
RIDE C   (  73,X'S) H   ( 731,X'S) H   ( 732,X'S) 
RIDE C   (  74,X'S) H   ( 741,X'S) H   ( 742,X'S) 
RIDE C   (  75,X'S) H   ( 751,X'S) H   ( 752,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
REM ANGLE 90, 0.3 = P(1) TO IR(1) TO H(1) 
REM ANGLE 90, 0.3 = C(1) TO IR(1) TO H(1) 
REM DIST 1.5, 0.08 = IR(1) TO H(1) 
U(IJ) 0.0, 0.02 = C(76) TO O(78) 
U(IJ) 0.0, 0.02 = C(78) TO O(76) 
DIST 0.0, 0.02 = MEAN C(76) TO C(77), C(77) TO C(78) 
DIST 0.0, 0.02 = MEAN O(76) TO C(77), C(77) TO O(78) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
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