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_4123788
_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_formula_moiety         'C20 H23 N O5'
_chemical_formula_sum            'C20 H23 N O5'
_chemical_formula_weight         357.39
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-08-22
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_cell_angle_alpha                92.037(3)
_cell_angle_beta                 91.652(3)
_cell_angle_gamma                110.704(4)
_cell_formula_units_Z            4
_cell_length_a                   8.5810(3)
_cell_length_b                   9.1263(4)
_cell_length_c                   24.3122(11)
_cell_measurement_reflns_used    4660
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      75.0970
_cell_measurement_theta_min      5.1730
_cell_volume                     1778.13(14)
_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
;
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
;
XH, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9868
_diffrn_measured_fraction_theta_max 0.9438
_diffrn_measurement_details
;
  1 omega   36.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -60.0000 62

  2 omega  -49.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000   60.0000 84

  3 omega -117.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -37.0000   90.0000 92

  4 omega  -65.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   57.0000 -120.0000 98

  5 omega   25.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8203 -125.0000  -30.0000 73

  6 omega   58.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000    0.0000 86

  7 omega   32.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000 -180.0000 81

  8 omega   69.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  178.0000  -60.0000 53

  9 omega   86.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -30.0000 29

 10 omega   34.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 56

 11 omega   34.00   60.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -30.0000 26

 12 omega   36.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 54

 13 omega   56.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000 -150.0000 87

 14 omega   30.00  172.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703    0.0000   30.0000 142
;
_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      -0.0558253000
_diffrn_orient_matrix_UB_12      0.0566860000
_diffrn_orient_matrix_UB_13      0.0538335000
_diffrn_orient_matrix_UB_21      0.0241767000
_diffrn_orient_matrix_UB_22      0.1592285000
_diffrn_orient_matrix_UB_23      -0.0247607000
_diffrn_orient_matrix_UB_31      -0.1822282000
_diffrn_orient_matrix_UB_32      -0.0638481000
_diffrn_orient_matrix_UB_33      -0.0227391000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10014
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         5.19
_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    0.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81011
_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            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         6289
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0750P)^2^+0.2800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                5366
_reflns_number_total             6289
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja5b03083_si_003.cif
_cod_data_source_block           bin11cult
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        1778.12(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4123788
_reflns_odcompleteness_completeness 98.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13