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_1513926
_publ_section_title
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 Aminodiols via Stereocontrolled Oxidation of Methyleneaziridines.
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_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         '3(C16 H20 F3 N O4), 2(C4 H8 O2)'
_chemical_formula_sum            'C56 H76 F9 N3 O16'
_chemical_formula_weight         1218.19
_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
_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                95.649(4)
_cell_angle_beta                 97.703(4)
_cell_angle_gamma                95.445(4)
_cell_formula_units_Z            2
_cell_length_a                   13.7974(9)
_cell_length_b                   14.6937(12)
_cell_length_c                   15.3341(12)
_cell_measurement_reflns_used    9741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.588
_cell_measurement_theta_min      2.926
_cell_volume                     3047.3(4)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            59282
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         79.837
_diffrn_reflns_theta_min         2.927
_exptl_absorpt_coefficient_mu    0.981
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6632
_exptl_absorpt_correction_type   analytical
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.358
_refine_diff_density_min         -0.939
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     806
_refine_ls_number_reflns         12542
_refine_ls_number_restraints     136
_refine_ls_restrained_S_all      1.151
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0667
_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^)+(0.0650P)^2^+4.1950P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1630
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10321
_reflns_number_total             12542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5003576_si_002.cif
_cod_data_source_block           schomaker12
_cod_database_code               1513926
_shelxl_version_number           2014-1
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.707
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 F1B-F2B \\sim F1B-F3B \\sim F2B-F3B \\sim F1C-F2C \\sim F1C-F3C \\sim F2C-F3C
\\sim F1D-F2D \\sim F1D-F3D
 \\sim F2D-F3D
 with sigma of 0.002
 C16B-F1B \\sim C16B-F2B \\sim C16B-F3B \\sim C16B-F1C \\sim C16B-F2C \\sim
C16B-F3C \\sim C16B-F1D ~
 C16B-F2D \\sim C16B-F3D
 with sigma of 0.003
 C13B-F1B \\sim C13B-F2B \\sim C13B-F3B \\sim C13B-F1C \\sim C13B-F2C \\sim
C13B-F3C \\sim C13B-F1D ~
 C13B-F2D \\sim C13B-F3D
 with sigma of 0.004
 O2T-C2S \\sim O2S-C2S \\sim O4S-C6S \\sim O4T-C6S
 with sigma of 0.003
 C6S-C5S \\sim C6S-C5T \\sim C2S-C1S
 with sigma of 0.003
 O2T-C3T \\sim O2S-C3S \\sim O4T-C7T \\sim O4S-C7S
 with sigma of 0.003
 C4S-C3S \\sim C4T-C3T \\sim C8S-C7S \\sim C8T-C7T
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C4T) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.04
Uanis(O4S) = Uanis(O4T)
Uanis(C8S) = Uanis(C7S) = Uanis(C8T) = Uanis(C7T)
Uanis(C5S) = Uanis(C5T)
Uanis(O2S) = Uanis(O2T)
Uanis(C16B) = Uanis(F1B) = Uanis(F2B) = Uanis(F3B) = Uanis(F1C) = Uanis(F2C) =
Uanis(F3C) = Uanis(F1D) = Uanis(F2D) = Uanis(F3D)
4. Others
 1*[Sof(F1B)+Sof(F2B)+Sof(F3B)]+1*[Sof(F1C)+Sof(F2C)+Sof(F3C)]+1*[Sof(F1D)+
 Sof(F2D)+Sof(F3D)]=1 with esd of 0
 Sof(O4T)=Sof(C5T)=Sof(H5TA)=Sof(H5TB)=Sof(H5TC)=Sof(C7T)=Sof(H7TA)=Sof(H7TB)=
 Sof(C8T)=Sof(H8TA)=Sof(H8TB)=Sof(H8TC)=1-FVAR(1)
 Sof(O4S)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=Sof(H5SC)=Sof(C7S)=Sof(H7SA)=Sof(H7SB)=
 Sof(C8S)=Sof(H8SA)=Sof(H8SB)=Sof(H8SC)=FVAR(1)
 Sof(O2T)=Sof(C3T)=Sof(H3TA)=Sof(H3TB)=Sof(C4T)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=
 1-FVAR(2)
 Sof(O2S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(H4SC)=
 FVAR(2)
 Sof(F1B)=Sof(F2B)=Sof(F3B)=FVAR(3)
 Sof(F1C)=Sof(F2C)=Sof(F3C)=FVAR(4)
 Sof(F1D)=Sof(F2D)=Sof(F3D)=FVAR(5)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C7(H7), C6A(H6A), C7A(H7A), C6B(H6B), C7B(H7B)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C2A(H2AA,H2AB), C2B(H2BA,H2BB), C3S(H3SA,H3SB), C3T(H3TA,H3TB),
 C7S(H7SA,H7SB), C7T(H7TA,H7TB)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C14(H14), C15(H15), N1A(H1A), C11A(H11A),
 C12A(H12A), C14A(H14A), C15A(H15A), N1B(H1B), C11B(H11B), C12B(H12B),
 C14B(H14B), C15B(H15B)
5.d Idealised Me refined with riding coordinates:
 C1S(H1SA,H1SB,H1SC), C5S(H5SA,H5SB,H5SC), C8S(H8SA,H8SB,H8SC), C5T(H5TA,H5TB,
 H5TC), C8T(H8TA,H8TB,H8TC)
5.e Idealised Me refined as rotating group:
 C4(H4A,H4C,H4D), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C4A(H4AB,H4AC,H4AD),
 C5A(H5AA,H5AB,H5AC), C9A(H9AA,H9AB,H9AC), C4B(H4BA,H4BB,H4BC), C5B(H5BA,H5BB,
 H5BC), C9B(H9BA,H9BB,H9BC), C4S(H4SA,H4SB,H4SC), C4T(H4TA,H4TB,H4TC)
5.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O3A(H3A), O4A(H4AA), O3B(H3B), O4B(H4B)
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_shelx_res_checksum              1643
_shelx_hkl_checksum              81821