Catalytic enantioselective epoxidation of nitroalkenes.
Vidal-Albalat, A; Swiderek, K.; Izquierdo, J.; Rodríguez, S; Moliner, V.; González, F V; Chemical communications (Cambridge, England) 52 (2016) 10060–10063; doi:10.1039/c6cc03539f

data_7124676
_publ_section_title
;
 Catalytic enantioselective epoxidation of nitroalkenes.
;
_journal_issue                   65
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10060
_journal_page_last               10063
_journal_paper_doi               10.1039/c6cc03539f
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_chemical_name_systematic        (2S,3R)-2-nitro-2,3-diphenyloxirane
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-30
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2016-02-22 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.415(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.6028(3)
_cell_length_b                   6.2292(3)
_cell_length_c                   11.4861(4)
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      71.1810
_cell_measurement_theta_min      3.8500
_cell_volume                     613.70(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      200
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9552
_diffrn_measurement_details
;
  1 omega -130.00  -35.80   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307 -178.0000   90.0000 157

  2 omega -116.00   -5.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000  -30.0000 185

  3 omega -122.00   19.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -19.0000   60.0000 235

  4 omega -122.00   -2.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -77.0000  -90.0000 200

  5 omega  -40.00   69.20   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307  -57.0000 -120.0000 182

  6 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  -30.0000 177

  7 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  -60.0000 177

  8 omega   76.00  178.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  -60.0000 170

  9 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -60.0000 172

 10 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000 -120.0000 172

 11 omega   76.00  178.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000   30.0000 170

 12 omega   28.00   97.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000   30.0000 115

 13 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -30.0000 172

 14 omega   20.00  108.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -94.0000 -120.0000 147

 15 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000  -90.0000 177

 16 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000 -120.0000 177

 17 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000  -90.0000 172

 18 omega   74.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   61.0000    0.0000 172

 19 omega   76.00  178.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   45.0000  -30.0000 170

 20 omega   26.00   89.60   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -30.0000  -90.0000 106

 21 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000    0.0000 177

 22 omega   25.00  115.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524 -111.0000   60.0000 150

 23 omega -116.00   -5.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000 -120.0000 185

 24 omega -122.00   -2.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -77.0000   90.0000 200

 25 omega  -49.00   41.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307   37.0000  150.0000 150

 26 omega -116.00   -5.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307  -57.0000  150.0000 185

 27 omega  -49.00   41.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -37.7307   37.0000    0.0000 150

 28 omega   57.00  129.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307  178.0000  150.0000 120

 29 omega    2.00  122.00   0.6000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       37.7307   77.0000 -180.0000 200

 30 omega   71.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   77.0000 -180.0000 177

 31 omega   28.00   97.00   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524  -45.0000 -120.0000 115

 32 omega   71.00  122.60   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   65.0000   61.8081 86

 33 omega   26.00  177.20   0.6000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      106.7524   15.0000 -180.0000 252
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0211234000
_diffrn_orient_matrix_UB_12      0.0730286000
_diffrn_orient_matrix_UB_13      -0.1259404000
_diffrn_orient_matrix_UB_21      -0.1709302000
_diffrn_orient_matrix_UB_22      -0.0591214000
_diffrn_orient_matrix_UB_23      -0.0357228000
_diffrn_orient_matrix_UB_31      -0.0509226000
_diffrn_orient_matrix_UB_32      0.2287035000
_diffrn_orient_matrix_UB_33      0.0311436000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9996
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_min         3.86
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.5590
_exptl_crystal_size_mid          0.1000
_exptl_crystal_size_min          0.0726
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2130
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0541
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1023P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1324
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                1941
_reflns_number_total             2130
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03539f2.cif
_cod_data_source_block           str1709
_cod_database_code               7124676
_chemical_oxdiff_formula         'C14 H11 N O2'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97