Rh2(R-TPCP)4- Catalyzed Enantioselective [3+2]-Cycloaddition between Nitrones and Vinyldiazoacetates
Changming Qin; Huw M. L. Davies; Journal of the American Chemical Society 135 (2013) 14516–14519; doi:10.1021/ja4069003

data_4120892
_publ_section_title
;
 Rh2(R-TPCP)4- Catalyzed Enantioselective [3+2]-Cycloaddition between
 Nitrones and Vinyldiazoacetates
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14516
_journal_page_last               14519
_journal_paper_doi               10.1021/ja4069003
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2(C18 H19 N O2)'
_chemical_formula_sum            'C36 H38 N2 O4'
_chemical_formula_weight         562.68
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2012-12-18
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.519(3)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   6.5770(2)
_cell_length_b                   13.6444(5)
_cell_length_c                   8.0893(3)
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.936
_cell_measurement_theta_min      6.362
_cell_volume                     725.67(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_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  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       '\f and \w scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4212
_diffrn_reflns_point_group_measured_fraction_full 0.809
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         68.095
_diffrn_reflns_theta_min         5.470
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0394 before and 0.0223 after correction.
The Ratio of minimum to maximum transmission is 0.8936.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.652
_exptl_crystal_size_mid          0.563
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 793 quotients [(I+)-I(-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2136
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0348P)^2^+0.0898P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0599
_reflns_Friedel_coverage         0.606
_reflns_Friedel_fraction_full    0.641
_reflns_Friedel_fraction_max     0.635
_reflns_number_gt                2107
_reflns_number_total             2136
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja4069003_si_002.cif
_cod_data_source_block           qin1322
_cod_database_code               4120892
_diffrn_reflns_sigmai/neti       0.0159
_olex2_refinement_description
;
1. Restrained distances
 C12-H12 ~ C11-H11 ~ C10-H10 ~ C14-H14 ~ C13-H13
 with sigma of 0.005
 C5-H5B ~ C5-H5A ~ C6-H6A ~ C6-H6B
 with sigma of 0.005
 C16-H16 ~ C17-H17 ~ C18-H18 ~ C19-H19 ~ C20-H20
 with sigma of 0.005
 C21-H21C ~ C21-H21B ~ C21-H21A
 with sigma of 0.005
2. Uiso/Uaniso restraints and constraints
Uiso(H10) = Uiso(H11) = Uiso(H12) = Uiso(H13) = Uiso(H14)
Uiso(H5A) = Uiso(H5B) = Uiso(H6A) = Uiso(H6B)
Uiso(H20) = Uiso(H19) = Uiso(H18) = Uiso(H17) = Uiso(H16)
Uiso(H21C) = Uiso(H21B) = Uiso(H21A)
;
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.671
_shelx_res_checksum              73692
_shelxl_version_number           2012-4