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_4079630
_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         'C37 H56 N2 P2.00'
_chemical_formula_sum            'C37 H56 N2 P2'
_chemical_formula_weight         590.81
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 115.196(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8797(7)
_cell_length_b                   11.8950(7)
_cell_length_c                   18.4555(8)
_cell_measurement_reflns_used    89385
_cell_measurement_temperature    200
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.55
_cell_volume                     3353.0(3)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.117
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34740
_diffrn_reflns_theta_full        25.091
_diffrn_reflns_theta_max         25.091
_diffrn_reflns_theta_min         2.667
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.43
_refine_ls_extinction_coef       1050(150)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     435
_refine_ls_number_reflns         5910
_refine_ls_number_restraints     56
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.0075182
_refine_ls_shift/su_mean         0.0009659
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 9.73P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2283
_refine_ls_wR_factor_gt          0.2147
_refine_ls_wR_factor_ref         0.2283
_reflns_limit_h_max              18
_reflns_limit_h_min              -20
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4363
_reflns_number_total             5932
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.61
_oxford_diffrn_Wilson_scale      3.76
_oxford_refine_ls_r_factor_ref   0.1169
_oxford_refine_ls_scale          0.589(3)
_oxford_reflns_number_all        5910
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            om300897w_si_003.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/a 1 '
_cod_original_formula_sum        'C37 H56 N2 P2.00'
_cod_database_code               4079630
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE C(1, X'S, U'S) UNTIL C(66) 
CONT C(510, X'S, U'S, OCC) UNTIL C(561) 
CONT N(1, X'S, U'S) UNTIL P(1) 
CONT P(20, X'S, U'S, OCC) UNTIL P(21) 
EQUIV P(20, OCC), P(21, OCC), C(510, OCC), C(511, OCC) 
CONT C(520, OCC), C(521, OCC), C(530, OCC), C(531, OCC) 
CONT C(540, OCC), C(541, OCC), C(550, OCC), C(551, OCC) 
CONT C(560, OCC), C(561, OCC) 
WEIGHT -1 P(20, OCC), C(510, OCC), C(520, OCC), C(530, OCC) 
CONT C(540, OCC), C(550, OCC), C(560, OCC) 
CONT EXTPARAM 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,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   (  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   ( 510,X'S) H   (5101,X'S) 
RIDE C   ( 511,X'S) H   (5111,X'S) 
RIDE C   ( 520,X'S) H   (5201,X'S) H   (5202,X'S) 
RIDE C   ( 521,X'S) H   (5211,X'S) H   (5212,X'S) 
RIDE C   ( 530,X'S) H   (5301,X'S) H   (5302,X'S) 
RIDE C   ( 531,X'S) H   (5311,X'S) H   (5312,X'S) 
RIDE C   ( 540,X'S) H   (5401,X'S) H   (5402,X'S) 
RIDE C   ( 541,X'S) H   (5411,X'S) H   (5412,X'S) 
RIDE C   ( 550,X'S) H   (5501,X'S) H   (5502,X'S) 
RIDE C   ( 551,X'S) H   (5511,X'S) H   (5512,X'S) 
RIDE C   ( 560,X'S) H   (5601,X'S) H   (5602,X'S) 
RIDE C   ( 561,X'S) H   (5611,X'S) H   (5612,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
U(IJ) 0.0, 0.01 = P(20) TO P(21) 
U(IJ) 0.0, 0.01 = C(510) TO C(511) 
U(IJ) 0.0, 0.01 = C(520) TO C(521) 
U(IJ) 0.0, 0.01 = C(530) TO C(531) 
U(IJ) 0.0, 0.01 = C(540) TO C(541) 
U(IJ) 0.0, 0.01 = C(550) TO C(551) 
U(IJ) 0.0, 0.01 = C(560) TO C(561) 
DIST 0.0, 0.02 = MEAN C(510) TO P(20), C(511) TO P(21) 
DIST 0.0, 0.02 = MEAN C(510) TO C(520), C(511) TO C(521) 
DIST 0.0, 0.02 = MEAN C(520) TO C(530), C(521) TO C(531) 
DIST 0.0, 0.02 = MEAN C(530) TO C(540), C(531) TO C(541) 
DIST 0.0, 0.02 = MEAN C(540) TO C(550), C(541) TO C(551) 
DIST 0.0, 0.02 = MEAN C(550) TO C(560), C(551) TO C(561) 
DIST 0.0, 0.02 = MEAN C(560) TO C(510), C(561) TO C(511) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;