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_1514976
_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 ad
_chemical_formula_moiety         'C16 H20 N2 O6'
_chemical_formula_sum            'C16 H20 N2 O6'
_chemical_formula_weight         336.34
_chemical_name_systematic
;
(+)-Ethyl (2R,4S-dinitro-3R-phenyl-1S-cyclohexyl) acetate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2011-07-15
_audit_creation_method
;
Olex2 1.1
(compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.0
_cell_angle_beta                 90.0
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_cell_formula_units_Z            4
_cell_length_a                   7.95486(5)
_cell_length_b                   10.00542(6)
_cell_length_c                   20.80472(17)
_cell_measurement_reflns_used    36335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.0830
_cell_measurement_theta_min      4.2466
_cell_volume                     1655.88(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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-97 (Sheldrick, 1997)'
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_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3468
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_diffrn_measurement_details
;
1 omega -34.00 -9.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
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2 omega -92.00 -1.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
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3 omega 0.00 91.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 41.1029 21.0000 -82.0000 91

4 omega -105.00 -80.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
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5 omega -105.00 -80.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- -61.5000 -21.0000 110.0000 25

6 omega 26.00 90.00 1.0000 12.0000
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7 omega 69.00 158.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 21.0000 -82.0000 89

8 omega 40.00 65.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 -21.0000 -68.0000 25

9 omega 65.00 101.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 21.0000 -110.0000 36

10 omega 29.00 141.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 -77.0000 120.0000 112

11 omega 32.00 98.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 -45.0000 -30.0000 66

12 omega 32.00 98.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 -45.0000 120.0000 66

13 omega -117.00 -15.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 -38.0000 0.0000 102

14 omega -50.00 35.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 38.0000 150.0000 85

15 omega -38.00 75.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 41.1029 -77.0000 -90.0000 113

16 omega -140.00 -28.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- -61.5000 -77.0000 -60.0000 112

17 omega -140.00 -28.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- -61.5000 -77.0000 -150.0000 112

18 omega 80.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 45.0000 150.0000 98

19 omega 29.00 141.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 -77.0000 -30.0000 112

20 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 60.0000 104

21 omega 46.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 15.0000 30.0000 132

22 omega -120.00 -7.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 -77.0000 -30.0000 113

23 omega -75.00 38.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 77.0000 -180.0000 113

24 omega 7.00 120.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 41.1029 77.0000 120.0000 113

25 omega -140.00 -28.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
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26 omega 29.00 141.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 -77.0000 -120.0000 112

27 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 90.0000 104

28 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 -30.0000 104

29 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 -180.0000 104

30 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 -90.0000 104

31 omega -50.00 35.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 38.0000 60.0000 85

32 omega -120.00 -7.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 -77.0000 150.0000 113

33 omega -120.00 -7.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 -77.0000 -120.0000 113

34 omega -140.00 -28.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- -61.5000 -77.0000 120.0000 112

35 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 -120.0000 104

36 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 150.0000 104

37 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 30.0000 104

38 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 -60.0000 104

39 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- 107.2551 77.0000 0.0000 104

40 omega -75.00 38.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- -41.1029 77.0000 -150.0000 113

41 omega -120.00 -7.00 1.0000 4.0000
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- -41.1029 -77.0000 60.0000 113

42 omega -38.00 75.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 41.1029 -77.0000 0.0000 113

43 omega -140.00 -28.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
- -61.5000 -77.0000 150.0000 112

44 omega -140.00 -28.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
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45 omega -140.00 -28.00 1.0000 12.0000
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46 omega -140.00 -28.00 1.0000 12.0000
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- -61.5000 -77.0000 60.0000 112

47 omega 29.00 141.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
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48 omega 74.00 178.00 1.0000 12.0000
omega____ theta____ kappa____ phi______ frames
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49 omega -117.00 -15.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
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50 omega 7.00 120.00 1.0000 4.0000
omega____ theta____ kappa____ phi______ frames
- 41.1029 77.0000 30.0000 113

;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
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_diffrn_radiation_type           'Cu K\a'
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_diffrn_reflns_av_sigmaI/netI    0.0355
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_exptl_absorpt_coefficient_mu    0.870
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_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_preparation       'heptane / DCM'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(11)
_refine_ls_extinction_coef       0.0022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3142
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0211
_refine_ls_shift/su_max          0.038
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.2258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0562
_reflns_number_gt                3111
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_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00592h.txt
_cod_data_source_block           Crystal3A
_cod_database_code               1514976
_chemical_oxdiff_formula         'C16 H20 N2 O6'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_theta     66.49
_reflns_odcompleteness_iscentric 1