Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via an Allene Aziridination Strategy.
Gerstner, Nels C.; Adams, Christopher S.; Grigg, R. David; Tretbar, Maik; Rigoli, Jared W.; Schomaker, Jennifer M.; Organic letters 18 (2016) 284–287; doi:10.1021/acs.orglett.5b03453

data_1541913
_publ_section_title
;
 Diastereoselective Synthesis of the Aminocyclitol Core of Jogyamycin via
 an Allene Aziridination Strategy.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              284
_journal_page_last               287
_journal_paper_doi               10.1021/acs.orglett.5b03453
_journal_volume                  18
_journal_year                    2016
_chemical_compound_source        'Schomaker Lab No. NCG2072'
_chemical_formula_moiety         'C14 H25 N O5 S Si'
_chemical_formula_sum            'C14 H25 N O5 S Si'
_chemical_formula_weight         347.50
_chemical_melting_point          ?
_chemical_name_systematic
;
1-((4S,5R)-5-((tert-butyldimethylsilyl)oxy)-4-ethynyl-2,2-dioxido-
1,2,3-oxathiazepan-4-yl)ethanone
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.204(3)
_cell_length_b                   10.0147(17)
_cell_length_c                   11.186(2)
_cell_measurement_reflns_used    9514
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      72.7116
_cell_measurement_theta_min      4.4150
_cell_volume                     1815.2(6)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle 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_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29296
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         73.018
_diffrn_reflns_theta_min         4.415
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    2.404
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6591
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'SADABS 2012'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method
'crystallized from diethyl ether and pentane using vapor diffusion.'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.996
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1531 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.046(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3495
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0574P)^2^+0.6694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                3456
_reflns_number_total             3495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03453_si_003.cif
_cod_data_source_block           schomaker42
_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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1541913--1541914.cif.
;
_cod_original_cell_volume        1815.1(6)
_cod_database_code               1541913
_shelx_res_checksum              1582
_shelx_hkl_checksum              52662