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_1516109
_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_absolute_configuration unk
_chemical_compound_source        'Schomaker Lab No. CSA5060'
_chemical_formula_moiety         'C20 H31 N O6 S Si'
_chemical_formula_sum            'C20 H31 N O6 S Si'
_chemical_formula_weight         441.62
_chemical_melting_point          ?
_chemical_name_common
'5-((tert-butyldimethylsilyl)oxy)-6-phenethyl-tetrahydrooxazolo[3,4-c][1,2,3]oxathiazepin-8(3H)-one 1,1-dioxide'
_chemical_properties_physical    air-stable
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2013-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.282(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9812(5)
_cell_length_b                   22.209(2)
_cell_length_c                   14.9476(8)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100.0(15)
_cell_measurement_theta_max      72.219
_cell_measurement_theta_min      3.579
_cell_volume                     2303.6(3)
_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
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_diffrn_ambient_temperature      100.0(15)
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9893
_diffrn_measured_fraction_theta_max 0.9893
_diffrn_measurement_device       'three-cycle diffractometer'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           4
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35165
_diffrn_reflns_theta_full        26.0488
_diffrn_reflns_theta_max         26.05
_diffrn_reflns_theta_min         1.65
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I \ms'
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2732
_exptl_crystal_description       block
_exptl_crystal_F_000             945.2904
_exptl_crystal_recrystallization_method
'crystallized by slow vapor diffusion using n-hexanes overnight at rt'
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.135
_refine_diff_density_max         0.3600
_refine_diff_density_min         -0.3240
_refine_diff_density_rms         0.0421
_refine_ls_d_res_high            0.8092
_refine_ls_d_res_low             12.3492
_refine_ls_goodness_of_fit_ref   1.0490
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    65
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4513
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.0387
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0287
_refine_ls_shift/su_max          0.0101
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+1.1095P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -6
_reflns_number_gt                4344
_reflns_number_total             4513
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c4sc01214c5.cif
_cod_data_source_block           csa5060
_cod_depositor_comments
;
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.
;
_cod_original_cell_volume        2303.7(3)
_cod_database_code               1516109
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C7A \\sim C8A \\sim C9A \\sim C10A \\sim C11A \\sim C12A \\sim C13A \\sim C7B
\\sim C8B \\sim C9B \\sim C10B \\sim C11B \\sim C12B \\sim C13B: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Same fragment restrains
{C7A, C8A, C9A, C10A, C11A, C12A, C13A}
as
{C7B, C8B, C9B, C10B, C11B, C12B, C13B}
4. Others
 Sof(H6bc)=Sof(H6bd)=Sof(C7B)=Sof(H7Ba)=Sof(H7Bb)=Sof(C8B)=Sof(C9B)=Sof(H9B)=
 Sof(C10B)=Sof(H10B)=Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=
 Sof(H13B)=1-FVAR(1)
 Sof(H6aa)=Sof(H6ab)=Sof(C7A)=Sof(H7Aa)=Sof(H7Ab)=Sof(C8A)=Sof(C9A)=Sof(H9A)=
 Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C6(H6aa,H6ab), C6(H6bc,H6bd), C7A(H7Aa,H7Ab),
 C7B(H7Ba,H7Bb)
5.c Aromatic/amide H refined with riding coordinates:
 C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A), C13A(H13A), C9B(H9B),
 C10B(H10B), C11B(H11B), C12B(H12B), C13B(H13B)
5.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C17(H17a,H17b,
 H17c), C18(H18a,H18b,H18c)
;