Highly enantioselective hydroamination to six-membered rings by heterobimetallic catalysts
Lenard Hussein; Nibadita Purkait; Mustafa Biyikal; Eugenia Tausch; Peter W. Roesky; Siegfried Blechert; Chem.Commun. 50 (2014) 3862–; doi:10.1039/C3CC48874H

data_7112167
_publ_section_title
;
 Highly enantioselective hydroamination to six-membered rings by
 heterobimetallic catalysts
;
_journal_name_full               Chem.Commun.
_journal_page_first              3862
_journal_paper_doi               10.1039/C3CC48874H
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C38 H44 N4 O3 S Zn'
_chemical_formula_sum            'C38 H44 N4 O3 S Zn'
_chemical_formula_weight         702.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2013-10-07
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1989(6)
_cell_length_b                   11.6090(7)
_cell_length_c                   36.4888(22)
_cell_measurement_reflns_used    4501
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.31
_cell_measurement_theta_min      1.12
_cell_volume                     3473.0(4)
_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      100
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1743
_diffrn_reflns_av_unetI/netI     0.2410
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            22651
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         1.116
_diffrn_source                   'Mo LFF Sealed Tube'
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.875
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
  Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)]
  (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6272
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.806
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0657
_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^)]
  where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3087
_reflns_number_total             6272
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3cc48874h2.cif
_cod_data_source_block           Zn2
_cod_original_cell_volume        3473.1(4)
_cod_database_code               7112167
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
  At 1.2 times of:
   All C(H) groups, All C(H,H) groups, All N(H) groups
  At 1.5 times of:
   All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C4) \\sim Ueq: with sigma of 0.006 and sigma for terminal atoms of
0.012
3. Others
  Fixed Sof: H29(0.35) H29A(0.65) C30A(0.35) H30A(0.65) H30B(0.65)
H30C(0.65)
  C30B(0.65) H30D(0.35) H30E(0.35) H30F(0.35)
4.a Ternary CH refined with riding coordinates:
  C1(H1), C2(H2), C14(H14), C29(H29), C29(H29A)
4.b Secondary CH2 refined with riding coordinates:
  C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
4.c Me refined with riding coordinates:
  C30A(H30A,H30B,H30C), C30B(H30D,H30E,H30F)
4.d Aromatic/amide H refined with riding coordinates:
  C7(H7), C11(H11), C12(H12), C13(H13), C17(H17), C18(H18), C19(H19),
C20(H20),
  C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C32(H32), C33(H33),
C34(H34),
   C35(H35), C36(H36), N3(H3), N4(H4)
4.e Idealised Me refined as rotating group:
  C15(H15A,H15B,H15C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
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