Synthesis of Heavy Fluorous Ruthenium Metathesis Catalysts Using the Stereoselective Addition of Polyfluoroalkyllithium to Sterically Hindered Diimines
Hošek, Jan; Rybáčková, Markéta; Čejka, Jan; Cvačka, Josef; Kvíčala, Jaroslav; Organometallics 34 (2015) 3327–; doi:10.1021/acs.organomet.5b00325

data_4086010
_publ_section_title
;
 Synthesis of Heavy Fluorous Ruthenium Metathesis Catalysts Using the
 Stereoselective Addition of Polyfluoroalkyllithium to Sterically Hindered
 Diimines
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3327
_journal_paper_doi               10.1021/acs.organomet.5b00325
_journal_volume                  34
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H34 F26 N2'
_chemical_formula_sum            'C36 H34 F26 N2'
_chemical_formula_weight         988.63
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2672(5)
_cell_length_b                   13.6532(6)
_cell_length_c                   32.0430(16)
_cell_measurement_reflns_used    8088
_cell_measurement_temperature    180
_cell_measurement_theta_max      77
_cell_measurement_theta_min      5
_cell_volume                     4054.3(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_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      180
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16425
_diffrn_reflns_theta_full        72.628
_diffrn_reflns_theta_max         77.264
_diffrn_reflns_theta_min         4.772
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  0.63
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.50
_refine_diff_density_min         -0.46
_refine_ls_abs_structure_details 'Flack (1983), 8108 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.3(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     740
_refine_ls_number_reflns         8290
_refine_ls_number_restraints     190
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0854
_refine_ls_shift/su_max          0.0004567
_refine_ls_shift/su_mean         0.0000147
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.12P)^2^ + 8.11P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2547
_refine_ls_wR_factor_gt          0.2507
_refine_ls_wR_factor_ref         0.2547
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                7214
_reflns_number_total             8293
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.33
_oxford_diffrn_Wilson_scale      0.10
_oxford_refine_ls_r_factor_ref   0.0910
_oxford_refine_ls_scale          3.68(9)
_oxford_reflns_number_all        8290
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            om5b00325_si_002.cif
_cod_data_source_block           jh226
_cod_depositor_comments
'Adding full bibliography for 4086010--4086011.cif.'
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4086010
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE N   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE N   (   4,X'S) H   (  41,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 113,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) H   ( 123,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) H   ( 133,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 202,X'S) H   ( 201,X'S) H   ( 203,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) H   ( 212,X'S) H   ( 213,X'S) 
RIDE C   (  22,X'S) H   ( 223,X'S) H   ( 222,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,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) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DELU 0.01 F(52) F(53) C(46) F(72) F(73) 
DELU 0.01 F(54) F(54) C(47) 
DELU 0.01 F(74) F(75) C(67) 
DELU 0.01 F(56) F(57) C(48) 
DELU 0.01 F(76) F(77) C(68) 
DELU 0.01 F(59) C(49) F(58) 
DELU 0.01 F(79) C(69) F(78) 
DELU 0.01 F(61) C(50) F(60) 
DELU 0.01 F(80) C(70) F(81) 
DELU 0.01 F(63) F(64) F(62) C(51) 
DELU 0.01 F(83) F(84) F(82) C(71) 
SIMU 0.01 F(52) F(53) C(46) F(72) F(73) 
SIMU 0.01 F(54) F(54) C(47) 
SIMU 0.01 F(74) F(75) C(67) 
SIMU 0.01 F(56) F(57) C(48) 
SIMU 0.01 F(76) F(77) C(68) 
SIMU 0.01 F(59) C(49) F(58) 
SIMU 0.01 F(79) C(69) F(78) 
SIMU 0.01 F(61) C(50) F(60) 
SIMU 0.01 F(80) C(70) F(81) 
SIMU 0.01 F(63) F(64) F(62) C(51) 
SIMU 0.01 F(83) F(84) F(82) C(71) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.340000 , 0.010000 = C(51) TO F(62) 
DISTANCE 1.340000 , 0.010000 = F(83) TO C(71) 
DISTANCE 1.340000 , 0.010000 = F(81) TO C(70) 
DISTANCE 1.550000 , 0.020000 = C(49) TO C(48) 
DISTANCE 1.550000 , 0.020000 = C(69) TO C(68) 
DISTANCE 1.550000 , 0.020000 = C(68) TO C(67) 
DISTANCE 1.550000 , 0.020000 = C(48) TO C(47) 
DISTANCE 1.340000 , 0.010000 = F(56) TO C(48) 
DISTANCE 1.340000 , 0.010000 = F(77) TO C(68) 
DISTANCE 1.340000 , 0.010000 = F(75) TO C(67) 
DISTANCE 1.550000 , 0.010000 = C(46) TO C(47) 
DISTANCE 1.550000 , 0.010000 = C(46) TO C(67) 
DISTANCE 1.350000 , 0.010000 = C(47) TO F(55) 
DISTANCE 1.350000 , 0.010000 = F(84) TO C(71) 
DISTANCE 1.350000 , 0.010000 = F(63) TO C(51) 
END                                                                             
;