Syntheses of Enantiopure Bifunctional 2-Guanidinobenzimidazole Cyclopentadienyl Ruthenium Complexes: Highly Enantioselective Organometallic Hydrogen Bond Donor Catalysts for Carbon‒Carbon Bond Forming Reactions
Mukherjee, Tathagata; Ganzmann, Carola; Bhuvanesh, Nattamai; Gladysz, John A.; Organometallics 33 (2014) 6723–; doi:10.1021/om500705s

data_4084830
_publ_section_title
;
 Syntheses of Enantiopure Bifunctional 2-Guanidinobenzimidazole
 Cyclopentadienyl Ruthenium Complexes: Highly Enantioselective
 Organometallic Hydrogen Bond Donor Catalysts for Carbon--Carbon Bond
 Forming Reactions
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6723
_journal_paper_doi               10.1021/om500705s
_journal_volume                  33
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H29 N6 O Ru, C18 Cl12 O6 P, 2(C4 H10 O)'
_chemical_formula_sum            'C48 H49 Cl12 N6 O9 P Ru'
_chemical_formula_weight         1411.37
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-06-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.025(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3215(5)
_cell_length_b                   13.8122(4)
_cell_length_c                   27.4488(8)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      62.368
_cell_measurement_theta_min      3.305
_cell_volume                     5659.4(3)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.798
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'BRUKER GADDS D8 Discover'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.798
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            73140
_diffrn_reflns_point_group_measured_fraction_full 0.754
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         59.993
_diffrn_reflns_theta_min         1.652
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.226
_exptl_absorpt_correction_T_max  0.7522
_exptl_absorpt_correction_T_min  0.4630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0934 before and 0.0566 after correction.
The Ratio of minimum to maximum transmission is 0.6155.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       block
_exptl_crystal_F_000             2856
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 5708 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.006(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1403
_refine_ls_number_reflns         15448
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0384P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0720
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.705
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                13787
_reflns_number_total             15448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500705s_si_001.cif
_cod_data_source_block           jgb
_cod_depositor_comments
'Adding full bibliography for 4084830--4084831.cif.'
_cod_database_code               4084830
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.790
_shelx_estimated_absorpt_t_min   0.559
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H13B of N13B, H12B of N12B, H10B of N10B, H1B of N1B, H12
  of N12, H10 of N10, H1 of N1, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, H13 of N13
2. Restrained distances
 O3D-C2D \\sim O3E-C2D \\sim O3E-C4D \\sim O3D-C4D
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(O3D) = Uanis(O3E)
4. Others
 Sof(O3E)=Sof(H2DC)=Sof(H2DD)=Sof(H4DC)=Sof(H4DD)=1-FVAR(1)
 Sof(O3D)=Sof(H2DA)=Sof(H2DB)=Sof(H4DA)=Sof(H4DB)=FVAR(1)
5.a Riding coordinates:
 N12(H12), N13(H13), N12B(H12B)
5.b Ternary CH refined with riding coordinates:
 C14(H14), C19(H19), C14B(H14B), C19B(H19B)
5.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C15B(H15C,
 H15D), C16B(H16C,H16D), C17B(H17C,H17D), C18B(H18C,H18D), C2D(H2DA,H2DB),
 C2D(H2DC,H2DD), C4D(H4DA,H4DB), C4D(H4DC,H4DD), C2F(H2FA,H2FB), C4F(H4FA,H4FB),
  C2H(H2HA,H2HB), C4H(H4HA,H4HB), C2J(H2JA,H2JB), C4J(H4JA,H4JB)
5.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N10(H10), C4(H4), C5(H5), C6(H6), C7(H7), C25(H25), C26(H26),
 C27(H27), C28(H28), C29(H29), N1B(H1B), N10B(H10B), N13B(H13B), C4B(H4B),
 C5B(H5B), C6B(H6B), C7B(H7B), C25B(H25B), C26B(H26B), C27B(H27B), C28B(H28B),
 C29B(H29B)
5.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C21B(H21D,H21E,H21F), C22B(H22D,
 H22E,H22F), C1H(H1HA,H1HB,H1HC), C5D(H5DA,H5DB,H5DC), C1I(H1IA,H1IB,H1IC),
 C5F(H5FA,H5FB,H5FC), C1J(H1JA,H1JB,H1JC), C5H(H5HA,H5HB,H5HC), C1K(H1KA,H1KB,
 H1KC), C5J(H5JA,H5JB,H5JC)
;
_shelx_res_checksum              59651
_shelx_hkl_checksum              19024