Organocatalytic enantioselective construction of nitrocyclohexanes containing multiple chiral centres via a cascade reaction
Rajkumar, Sundaram; Shankland, Kenneth; Brown, Geoffrey D.; Cobb, Alexander J. A.; Chemical Science 3 (2012) 584–; doi:10.1039/c1sc00592h

data_1514978
_publ_section_title
;
 Organocatalytic enantioselective construction of nitrocyclohexanes
 containing multiple chiral centres via a cascade reaction
;
_journal_issue                   2
_journal_name_full               'Chemical Science'
_journal_page_first              584
_journal_paper_doi               10.1039/c1sc00592h
_journal_volume                  3
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C17 H22 N2 O6'
_chemical_formula_sum            'C17 H22 N2 O6'
_chemical_formula_weight         350.37
_chemical_name_systematic
;
ethyl 2-[(1S,2R,3R,4S)-2-methyl-2,4-dinitro-3-
phenylcyclohexyl]acetate
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.098(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1928(5)
_cell_length_b                   6.6518(4)
_cell_length_c                   12.7044(6)
_cell_measurement_reflns_used    3023
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.9050
_cell_measurement_theta_min      2.4920
_cell_volume                     860.11(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measurement_device_type  Gemini
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10366
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         2.50
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_preparation       'heptane / DCM'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0694P)^2^+0.0784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1457
_reflns_number_gt                2996
_reflns_number_total             3903
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c1sc00592h.txt
_cod_data_source_block           Crystal_3i
_cod_database_code               1514978