Complete stereodivergence in the synthesis of 2-amino-1,3-diols from allenes
Adams, Christopher S.; Grigg, R. David; Schomaker, Jennifer M.; Chemical Science 5 (2014) 3046–; doi:10.1039/c4sc01214c

data_1516107
_publ_section_title
;
 Complete stereodivergence in the synthesis of 2-amino-1,3-diols from
 allenes
;
_journal_issue                   8
_journal_name_full               'Chemical Science'
_journal_page_first              3046
_journal_paper_doi               10.1039/c4sc01214c
_journal_volume                  5
_journal_year                    2014
_chemical_formula_moiety         '1(C19 H33 N O5 S Si)'
_chemical_formula_sum            'C19 H33 N O5 S Si'
_chemical_formula_weight         415.61
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                72.829(6)
_cell_angle_beta                 75.377(7)
_cell_angle_gamma                75.493(6)
_cell_formula_units_Z            4
_cell_length_a                   11.8101(17)
_cell_length_b                   12.7217(17)
_cell_length_c                   16.841(2)
_cell_measurement_temperature    200(2)
_cell_volume                     2296.4(5)
_computing_cell_refinement       'SAINT+ Ver. 7.68A (Bruker-AXS, 2009)'
_computing_data_collection       'APEX2 Ver. 2012.14-3 (Bruker-AXS, 2012)'
_computing_data_reduction        'SAINT+ Ver. 7.68A'
_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
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      200.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'three-circle Bruker Quazar SMART APEXII'
_diffrn_measurement_method       '0.5\ \w and 0.5\ \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            54072
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_min         1.29
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2012'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.129
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     646
_refine_ls_number_reflns         11307
_refine_ls_number_restraints     379
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+0.7519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                9758
_reflns_number_total             11307
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4sc01214c5.cif
_cod_data_source_block           schomaker30
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value 'not determined' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516107--1516109.cif.
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_cod_original_cell_volume        2296.4(6)
_cod_database_code               1516107
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Si1A \\sim C14A \\sim C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A \\sim
Si1B \\sim C14B \\sim C15B \\sim C16B \\sim C17B \\sim C18B \\sim C19B \\sim
Si1C \\sim C14C \\sim C15C \\sim C16C \\sim C17C \\sim C18C \\sim C19C: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Same fragment restrains
{Si1A, O3, C14A, C15A, C16A, C17A, C18A, C19A}
{Si1B, O3, C14B, C15B, C16B, C17B, C18B, C19B}
{Si1C, O3, C14C, C15C, C16C, C17C, C18C, C19C}
as
{Si1, O3, C14, C15, C16, C17, C18, C19}
4. Others
 1*[Sof(Si1A)+Sof(C14A)+Sof(H14A)+Sof(H14B)+Sof(H14C)+Sof(C15A)+Sof(H15A)+
 Sof(H15B)+Sof(H15C)+Sof(C16A)+Sof(H16A)+Sof(H16B)+Sof(H16C)+Sof(C17A)+
 Sof(H17A)+Sof(H17B)+Sof(H17C)+Sof(C18A)+Sof(H18A)+Sof(H18B)+Sof(H18C)+
 Sof(C19A)]+1*[Sof(Si1B)+Sof(C14B)+Sof(H14D)+Sof(H14E)+Sof(H14F)+Sof(C15B)+
 Sof(H15D)+Sof(H15E)+Sof(H15F)+Sof(C16B)+Sof(H16D)+Sof(H16E)+Sof(H16F)+
 Sof(C17B)+Sof(H17D)+Sof(H17E)+Sof(H17F)+Sof(C18B)+Sof(H18D)+Sof(H18E)+
 Sof(H18F)+Sof(C19B)]+1*[Sof(Si1C)+Sof(C14C)+Sof(H14G)+Sof(H14H)+Sof(H14I)+
 Sof(C15C)+Sof(H15G)+Sof(H15H)+Sof(H15I)+Sof(C16C)+Sof(H16G)+Sof(H16H)+
 Sof(H16I)+Sof(C17C)+Sof(H17G)+Sof(H17H)+Sof(H17I)+Sof(C18C)+Sof(H18G)+
 Sof(H18H)+Sof(H18I)+Sof(C19C)]=1 with esd of 0
 Sof(Si1A)=Sof(C14A)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15A)=Sof(H15A)=
 Sof(H15B)=Sof(H15C)=Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17A)=
 Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=
 Sof(C19A)=FVAR(1)
 Sof(Si1B)=Sof(C14B)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C15B)=Sof(H15D)=
 Sof(H15E)=Sof(H15F)=Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17B)=
 Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18B)=Sof(H18D)=Sof(H18E)=Sof(H18F)=
 Sof(C19B)=FVAR(2)
 Sof(Si1C)=Sof(C14C)=Sof(H14G)=Sof(H14H)=Sof(H14I)=Sof(C15C)=Sof(H15G)=
 Sof(H15H)=Sof(H15I)=Sof(C16C)=Sof(H16G)=Sof(H16H)=Sof(H16I)=Sof(C17C)=
 Sof(H17G)=Sof(H17H)=Sof(H17I)=Sof(C18C)=Sof(H18G)=Sof(H18H)=Sof(H18I)=
 Sof(C19C)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C3A(H3A), C4A(H4A), C5A(H5A)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1B,H1C), C2(H2A,H2B), C6(H6B,H6C), C7(H7A,H7B), C1A(H1AA,H1AB), C2A(H2AA,
 H2AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C9A(H9A), C10A(H10A),
 C11A(H11A), C12A(H12A), C13A(H13A)
5.d Idealised Me refined as rotating group:
 C14(H14J,H14K,H14L), C15(H15J,H15K,H15L), C16(H16J,H16K,H16L), C17(H17J,H17K,
 H17L), C18(H18J,H18K,H18L), C14A(H14A,H14B,H14C), C15A(H15A,H15B,H15C),
 C16A(H16A,H16B,H16C), C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C), C14B(H14D,
 H14E,H14F), C15B(H15D,H15E,H15F), C16B(H16D,H16E,H16F), C17B(H17D,H17E,H17F),
 C18B(H18D,H18E,H18F), C14C(H14G,H14H,H14I), C15C(H15G,H15H,H15I), C16C(H16G,
 H16H,H16I), C17C(H17G,H17H,H17I), C18C(H18G,H18H,H18I)
5.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O6A(H6A)
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