Chiral magnesium(II)-catalyzed asymmetric ring-opening of meso-aziridines with primary alcohols
Jun Li; Yuting Liao; Yulong Zhang; Xiaohua Liu; Lili Lin; Xiaoming Feng; Chem.Commun. 50 (2014) 6672–; doi:10.1039/C4CC02206H

data_7113980
_publ_section_title
;
 Chiral magnesium(II)-catalyzed asymmetric ring-opening of meso-aziridines
 with primary alcohols
;
_journal_name_full               Chem.Commun.
_journal_page_first              6672
_journal_paper_doi               10.1039/C4CC02206H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C13 H17 Cl N2 O2'
_chemical_formula_sum            'C13 H17 Cl N2 O2'
_chemical_formula_weight         268.73
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                103.797(6)
_cell_angle_beta                 101.344(5)
_cell_angle_gamma                91.264(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0981(4)
_cell_length_b                   8.8180(7)
_cell_length_c                   10.4495(7)
_cell_measurement_reflns_used    1367
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6560
_cell_measurement_theta_min      3.5000
_cell_volume                     708.64(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0874
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0208578000
_diffrn_orient_matrix_UB_12      0.0174117000
_diffrn_orient_matrix_UB_13      0.0713795000
_diffrn_orient_matrix_UB_21      0.0352805000
_diffrn_orient_matrix_UB_22      -0.0734022000
_diffrn_orient_matrix_UB_23      -0.0033324000
_diffrn_orient_matrix_UB_31      0.0796422000
_diffrn_orient_matrix_UB_32      0.0347209000
_diffrn_orient_matrix_UB_33      -0.0005004000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6348
_diffrn_reflns_point_group_measured_fraction_full 0.766
_diffrn_reflns_point_group_measured_fraction_max 0.649
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.848
_diffrn_reflns_theta_min         2.938
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             284
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0862P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1940
_reflns_Friedel_coverage         0.493
_reflns_Friedel_fraction_full    0.534
_reflns_Friedel_fraction_max     0.429
_reflns_number_gt                2507
_reflns_number_total             4806
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc02206h2.cif
_cod_data_source_block           140304_s2_lj
_cod_original_cell_volume        708.63(8)
_cod_database_code               7113980
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         c12h12n2o4cl1
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Uiso/Uaniso restraints and constraints
Uanis(Cl3) = Uanis(Cl3A)
Uanis(Cl1) = Uanis(Cl1A)
Uanis(C26) = Uanis(C13)
3. Others
 Sof(Cl1A)=Sof(Cl3A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl3)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C14(H14), C15(H15), C1(H1), C2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C3(H3A,H3B),
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C24(H24), C25(H25), C9(H9), C11(H11), C12(H12), N1(H1A)
4.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              98406
_shelx_hkl_checksum              3564
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'