Catalytic enantioselective intermolecular desymmetrization of azetidines.
Wang, Zhaobin; Sheong, Fu Kit; Sung, Herman H. Y.; Williams, Ian D.; Lin, Zhenyang; Sun, Jianwei; Journal of the American Chemical Society 137 (2015) 5895–5898; doi:10.1021/jacs.5b03083

data_4123789
_publ_section_title
;
 Catalytic enantioselective intermolecular desymmetrization of azetidines.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5895
_journal_page_last               5898
_journal_paper_doi               10.1021/jacs.5b03083
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H29 N O5, 0.5(C Cl2)'
_chemical_formula_sum            'C27.5 H30 Cl N O5'
_chemical_formula_weight         489.98
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-02-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 104.037(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.7884(5)
_cell_length_b                   4.97790(9)
_cell_length_c                   20.9526(4)
_cell_measurement_reflns_used    4062
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      75.1850
_cell_measurement_theta_min      4.7060
_cell_volume                     2508.23(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
  1 omega  -40.00   28.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   37.0000  150.0000 68

  2 omega -121.00    3.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -19.0000  -30.0000 124

  3 omega   23.00   95.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  -60.0000 72

  4 omega   65.00   98.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9453 -125.0000  120.0000 33

  5 omega   33.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 57

  6 omega   33.00   72.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 39

  7 omega   33.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  120.0000 57

  8 omega   48.00  128.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000 -180.0000 80

  9 omega   28.00  133.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -15.0000 -150.0000 105

 10 omega  147.00  172.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -15.0000 -150.0000 25

 11 omega   35.00  105.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   30.0000 70

 12 omega   45.00  107.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  120.0000 62

 13 omega   87.00  141.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  178.0000   60.0000 54

 14 omega   33.00   90.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   60.0000 57

 15 omega  106.00  143.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000  150.0000 37
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0284928000
_diffrn_orient_matrix_UB_12      -0.0340015000
_diffrn_orient_matrix_UB_13      -0.0735444000
_diffrn_orient_matrix_UB_21      -0.0552219000
_diffrn_orient_matrix_UB_22      -0.0674898000
_diffrn_orient_matrix_UB_23      0.0178200000
_diffrn_orient_matrix_UB_31      -0.0156411000
_diffrn_orient_matrix_UB_32      0.3000195000
_diffrn_orient_matrix_UB_33      -0.0042779000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6479
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_min         4.71
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    1.663
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         3114
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+3.3105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2963
_reflns_number_total             3114
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b03083_si_002.cif
_cod_data_source_block           bin8a
_cod_original_cell_volume        2508.23(8)
_cod_original_formula_sum        'C27.50 H30 Cl N O5'
_cod_database_code               4123789
_chemical_oxdiff_formula         'Ph3 O5 N1 C8 Cl2'
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Restrained distances
 Cl2-C1S = Cl1-C1S
 1.72 with sigma of 0.02
 Cl3-C2S = Cl4-C2S
 1.72 with sigma of 0.02
3. Others
 Fixed Sof: C1S(0.4) Cl1(0.4) Cl2(0.4) C2S(0.1) Cl3(0.1) Cl4(0.1)
4.a Ternary CH refined with riding coordinates:
 C12(H12)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C23(H23), C24(H24), C25(H25), C26(H26), C27(H27)
4.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_olex2_date_sample_data_collection 2014-06-04
_olex2_submission_special_instructions 'No special instructions were received'