Aminodiols via Stereocontrolled Oxidation of Methyleneaziridines.
Rigoli, Jared W.; Guzei, Ilia A.; Schomaker, Jennifer M.; Organic letters 16 (2014) 1696–1699; doi:10.1021/ol5003576

data_1513925
_publ_section_title
;
 Aminodiols via Stereocontrolled Oxidation of Methyleneaziridines.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1696
_journal_page_last               1699
_journal_paper_doi               10.1021/ol5003576
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C27 H31 N3 O10'
_chemical_formula_sum            'C27 H31 N3 O10'
_chemical_formula_weight         557.55
_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
_audit_creation_date             2014-02-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.01.22 svn.r2872 for OlexSys, GUI svn.r4747)
;
_cell_angle_alpha                108.116(5)
_cell_angle_beta                 93.050(5)
_cell_angle_gamma                104.286(5)
_cell_formula_units_Z            2
_cell_length_a                   7.9880(7)
_cell_length_b                   13.4927(12)
_cell_length_c                   15.604(2)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.969
_cell_measurement_theta_min      3.010
_cell_volume                     1533.5(3)
_computing_cell_refinement       'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_data_collection       'APEX2 Ver. 2013.2-0 (Bruker-AXS, 2013)'
_computing_data_reduction        'SAINT+ Ver. 8.30C (Bruker-AXS, 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008-2013)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008-2013)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008-2013)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '0.60\ \w and 0.6\ \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  'equatorially mounted graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17922
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.266
_diffrn_reflns_theta_min         3.010
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0350 before and 0.0249 after correction.
The Ratio of minimum to maximum transmission is 0.9213.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5675
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0533P)^2^+0.6090P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5437
_reflns_number_total             5675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5003576_si_003.cif
_cod_data_source_block           schomaker14
_cod_original_cell_volume        1533.6(3)
_cod_database_code               1513925
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.859
_shelx_estimated_absorpt_t_min   0.745
_olex2_refinement_description
;
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. Others
 Sof(O6A)=Sof(O7A)=Sof(O8A)=Sof(O9A)=Sof(N3A)=Sof(C21A)=Sof(C22A)=Sof(C23A)=
 Sof(H23A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=
 Sof(H27A)=1-FVAR(1)
 Sof(O6)=Sof(O7)=Sof(O8)=Sof(O9)=Sof(N3)=Sof(C21)=Sof(C22)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24)=Sof(C25)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27)=FVAR(1)
 Uiso(O6A)=Uiso(O7A)=Uiso(O8A)=Uiso(O9A)=Uiso(N3A)=Uiso(C21A)=Uiso(C22A)=
 Uiso(C23A)=Uiso(C24A)=Uiso(C25A)=Uiso(C26A)=Uiso(C27A)=FVAR(2)
3.a Free rotating group:
 O6A(O7A,O8A,O9A,N3A,C21A,C22A,C23A,C24A,C25A,C26A,C27A)
3.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C14(H14)
3.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C20(H20A,H20B)
3.d Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C26(H26), C27(H27), C6(H6), C7(H7), C9(H9), C10(H10A),
 C23A(H23A), C24A(H24A), C26A(H26A), C27A(H27A)
3.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C)
3.f Idealised tetrahedral OH refined as rotating group:
 O10(H10)
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_shelx_res_checksum              27745
_shelx_hkl_checksum              99931
_shelx_fab_checksum              61675