Highly Z-Selective and Enantioselective Ring-Opening/Cross-Metathesis Catalyzed by a Resolved Stereogenic-at-Ru Complex
John Hartung; Robert H. Grubbs; Journal of the American Chemical Society 135 (2013) 10183–10185; doi:10.1021/ja4046422

data_4120122
_publ_contact_author_address
;
Beckman Institute
Caltech 139-74
Pasadena CA 91125
USA
;
_publ_contact_author_email       xray@caltech.edu
_publ_contact_author_name        'Xray Staff'
_publ_section_title
;
 Highly Z-Selective and Enantioselective Ring-Opening/Cross-Metathesis
 Catalyzed by a Resolved Stereogenic-at-Ru Complex
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10183
_journal_page_last               10185
_journal_paper_doi               10.1021/ja4046422
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C41 H50 N2 O4 Ru'
_chemical_formula_sum            'C41 H50 N2 O4 Ru'
_chemical_formula_weight         735.90
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2013-01-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385),
 SHELXL-2012,
 and manual edit
;
_cell_angle_alpha                90
_cell_angle_beta                 105.749(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6582(6)
_cell_length_b                   14.7827(9)
_cell_length_c                   12.9177(8)
_cell_measurement_reflns_used    9040
_cell_measurement_temperature    100
_cell_measurement_theta_max      42.71
_cell_measurement_theta_min      2.76
_cell_volume                     1775.08(19)
_computing_cell_refinement       'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_data_collection       'APEX2 2012.10-0 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.27B (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_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.
 and SHELXTL (Bruker-AXS, 2007)
;
_computing_structure_refinement  'SHELXL-2012/8 (Sheldrick, 2012)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            171955
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         43.711
_diffrn_reflns_theta_min         1.638
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.486
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0611 before and 0.0573 after correction.
The Ratio of minimum to maximum transmission is 0.9117.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'dichroic dark purple/pale blue'
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             772
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 10574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.009(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         26091
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.242
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0200P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0547
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.912
_reflns_number_gt                24002
_reflns_number_total             26091
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4046422_si_003.cif
_cod_data_source_block           jjh001
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_source_target' value 'MO' changed to 'Mo' according to the
built-in table from CIF Core dictionary named 'cif_core.dic' version
2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_database_code               4120122
_refine_ls_abs_structure_hooft   -0.007(4)
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H40 of C40, H39 of C39, H38 of C38, H37 of C37, H36 of C36, H34 of C34,
  {H7A,H7B} of C7, H8 of C8, {H9A,H9B} of C9, H10 of C10, {H11A,H11B} of C11,
  {H12A,H12B} of C12, {H13A,H13B} of C13, H16 of C16, H18 of C18, H23 of C23,
  H25 of C25, H26 of C26, H27 of C27, H28 of C28, H30 of C30, {H3A,H3B} of C3,
  {H2A,H2B} of C2, H5 of C5, H6 of C6
 At 1.5 times of:
  {H41A,H41B,H41C} of C41, {H32A,H32B,H32C} of C32, {H31A,H31B,H31C} of C31,
  {H20A,H20B,H20C} of C20, {H21A,H21B,H21C} of C21, {H22A,H22B,H22C} of C22
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C10(H10), C30(H30), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,
 H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C41(H41A,H41B,H41C)
;
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.856
_shelxl_version_number           2012-6