Asymmetric Ring-Opening of Donor‒Acceptor Cyclopropanes with Primary Arylamines Catalyzed by a Chiral Heterobimetallic Catalyst
Luo, Weiwei; Sun, Zhicheng; Fernando, E. H. Nisala; Nesterov, Vladimir N.; Cundari, Thomas R.; Wang, Hong; ACS Catalysis 9 (2019) 8285–; doi:10.1021/acscatal.9b02523

data_4514813
_publ_section_title
;
 Asymmetric Ring-Opening of Donor--Acceptor Cyclopropanes with Primary
 Arylamines Catalyzed by a Chiral Heterobimetallic Catalyst
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              8285
_journal_paper_doi               10.1021/acscatal.9b02523
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C80 H60 O22 P4 Yb2, C F3 O3 S, 3(C4 H8 O2)'
_chemical_formula_sum            'C93 H84 F3 O31 P4 S Yb2'
_chemical_formula_weight         2256.62
_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             2018-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1600(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.0655(2)
_cell_length_b                   17.2352(4)
_cell_length_c                   23.1949(3)
_cell_measurement_reflns_used    45360
_cell_measurement_temperature    99.99(13)
_cell_measurement_theta_max      27.4100
_cell_measurement_theta_min      1.8770
_cell_volume                     6794.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.12b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.12b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.12b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -20.00  17.00   0.50  141.00    --   -5.49 -77.00  60.00   74
  2  \w     -6.00  43.00   0.50  141.00    --    4.56-106.00 111.00   98
  3  \w     11.00  37.00   0.50  141.00    --    4.56 -99.00   0.00   52
  4  \w    -16.00  39.00   0.50  141.00    --    4.56 -99.00 -30.00  110
  5  \w    -13.00  22.00   0.50  141.00    --    4.56 -99.00 -90.00   70
  6  \w    -17.00   9.00   0.50  141.00    --   -5.49 -99.00 -90.00   52
  7  \w    -19.00   8.00   0.50  141.00    --   -5.49 -77.00-150.00   54
  8  \w    -41.00   8.00   0.50  141.00    --    4.56 -77.00-120.00   98
  9  \w    -17.00   8.00   0.50  141.00    --   -5.49 -99.00 -60.00   50
 10  \w    -15.00  28.00   0.50  141.00    --   -5.49 -99.00  30.00   86
 11  \w    -70.00  10.00   0.50  141.00    --    4.56 -37.00-180.00  160
 12  \w    -76.00   8.00   0.50  141.00    --   -5.49 -37.00 120.00  168
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0145247000
_diffrn_orient_matrix_UB_12      -0.0376286000
_diffrn_orient_matrix_UB_13      -0.0073115000
_diffrn_orient_matrix_UB_21      -0.0122022000
_diffrn_orient_matrix_UB_22      0.0130354000
_diffrn_orient_matrix_UB_23      -0.0283993000
_diffrn_orient_matrix_UB_31      0.0371681000
_diffrn_orient_matrix_UB_32      -0.0104311000
_diffrn_orient_matrix_UB_33      -0.0090782000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            116277
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.849
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.491
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.12b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_description       plate
_exptl_crystal_F_000             2266
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.362
_refine_diff_density_min         -1.101
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.158(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1028
_refine_ls_number_reflns         27766
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0595
_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^)+(0.0932P)^2^+8.1244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1599
_refine_ls_wR_factor_ref         0.1694
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                22362
_reflns_number_total             27766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02523_si_002.cif
_cod_data_source_block           str0097lt100kmo
_cod_database_code               4514813
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C90H50O20P4SF3Yb2
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.929
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.842(10)
 0.158(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H,H) groups
3. Restrained distances
 C2D-C3D
 2.3 with sigma of 0.01
 C13-C14 = C14-C15 = C15-C16 = C16-C17 = C17-C18
 1.4 with sigma of 0.01
 C54-C55 = C55-C56 = C58-C59 = C59-C60 = C60-C51
 1.4 with sigma of 0.01
 Yb1-O18
 2.3 with sigma of 0.02
 C1E-C2E = C3E-C4E
 1.5 with sigma of 0.01
 C7-C8 = C35-C36
 1.4 with sigma of 0.01
 C1D-O1D \\sim C4D-C3D \\sim C2D-O2D
 with sigma of 0.005
 C4E-C2E \\sim C1E-O2E \\sim O1E-C3E
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
Uanis(O4) = Uanis(O3)
Uanis(C1D) = Uanis(C2D)
Uanis(C4D) = Uanis(C3D)
Uanis(C58) = Uanis(C57)
Uanis(O11) = Uanis(O18)
Uanis(C24) = Uanis(C26) = Uanis(C27) = Uanis(C28)
Uanis(C74) = Uanis(C75) = Uanis(C76) = Uanis(C77)
Uanis(C54) = Uanis(C55) = Uanis(C56) = Uanis(C57) = Uanis(C58)
Uanis(C51) = Uanis(C52) = Uanis(C53) = Uanis(C54)
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5) = Uanis(C6) =
Uanis(C7) = Uanis(C8) = Uanis(C9) = Uanis(C10)
Uanis(C59) = Uanis(C60)
Uanis(C79) = Uanis(C80)
Uanis(Yb1) = Uanis(Yb2)
Uanis(C48) = Uanis(C47)
5.a Secondary CH2 refined with riding coordinates:
 C1C(H1CA,H1CB), C1D(H1DA,H1DB), C1E(H1EA,H1EB), C2C(H2CA,H2CB), C2D(H2DA,
 H2DB), C2E(H2EA,H2EB), C3C(H3CA,H3CB), C3D(H3DA,H3DB), C3E(H3EA,H3EB),
 C4C(H4CA,H4CB), C4D(H4DA,H4DB), C4E(H4EA,H4EB)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27),
  C29(H29), C30(H30), C34(H34), C35(H35), C36(H36), C37(H37), C39(H39),
 C40(H40), C44(H44), C45(H45), C46(H46), C47(H47), C49(H49), C50(H50), C54(H54),
  C55(H55), C56(H56), C57(H57), C59(H59), C60(H60), C64(H64), C65(H65),
 C66(H66), C67(H67), C69(H69), C70(H70), C74(H74), C75(H75), C76(H76), C77(H77),
  C79(H79), C80(H80)
5.c X=CH2 refined with riding coordinates:
 O17(H17A,H17B), O18(H18A,H18B), O19(H19A,H19B), O20(H20A,H20B), O21(H21A,
 H21B), O22(H22A,H22B)
;
_shelx_res_checksum              3991
_shelx_hkl_checksum              3812
_shelx_fab_checksum              3096
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.063
_oxdiff_exptl_absorpt_empirical_full_min 0.905