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_1513923
_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         'C12 H23 N O4'
_chemical_formula_sum            'C12 H23 N O4'
_chemical_formula_weight         245.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2012-10-22
_audit_creation_method
;
  Olex2 1.2-dev
  (compiled Oct 22 2012 15:55:03, GUI svn.r4359)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.094(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8620(9)
_cell_length_b                   9.1079(9)
_cell_length_c                   10.5256(14)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100.26
_cell_measurement_theta_max      67.341
_cell_measurement_theta_min      3.260
_cell_volume                     1299.4(2)
_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  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2008-2012)'
_diffrn_ambient_temperature      100.26
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.979
_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           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19859
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         67.830
_diffrn_reflns_theta_min         3.260
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens, K FFCU 2K 90'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.764
_exptl_absorpt_correction_T_max  0.8643
_exptl_absorpt_correction_T_min  0.7876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
wR2(int) was 0.0483 before and 0.0304 after correction.
The Ratio of minimum to maximum transmission is 0.9113.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.364
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0516P)^2^+0.5152P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0911
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2245
_reflns_number_total             2314
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5003576_si_006.cif
_cod_data_source_block           schomaker18
_cod_database_code               1513923
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H2A,H2B} of C2, {H11A,H11B} of C11, {H10A,H10B} of C10, {H3A,H3B} of C3,
  H4A of C4, H5 of C5, {H8A,H8B} of C8, {H9A,H9B} of C9
 At 1.5 times of:
  {H12A,H12B,H12C} of C12, {H7A,H7B,H7C} of C7
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C)
;
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.710
_shelx_hkl_checksum              34305
_shelx_res_checksum              13125
_shelxl_version_number           2012-6