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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/49/1514978.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1514978
loop_
_publ_author_name
'Rajkumar, Sundaram'
'Shankland, Kenneth'
'Brown, Geoffrey D.'
'Cobb, Alexander J. A.'
_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       'ω 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/[σ²(Fo²)+(0.0694P)²+0.0784P] where P=(Fo²+2Fc²)/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     >2σ(I)
_cod_data_source_file            c1sc00592h.txt
_cod_data_source_block           Crystal_3i
_cod_database_code               1514978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O6 O -0.8149(2) -0.4486(4) -0.02016(18) 0.0431(6) Uani 1 1 d .
O4 O -0.8583(2) 0.2855(3) -0.27308(17) 0.0366(5) Uani 1 1 d .
O5 O -0.9435(2) -0.2085(4) 0.02043(16) 0.0463(6) Uani 1 1 d .
N1 N -0.8814(2) 0.1604(4) -0.3432(2) 0.0285(6) Uani 1 1 d .
O1 O -1.3209(2) 0.3371(4) -0.3399(2) 0.0448(6) Uani 1 1 d .
O3 O -0.8835(3) 0.2005(4) -0.43637(18) 0.0462(6) Uani 1 1 d .
O2 O -1.3230(2) 0.0363(4) -0.4176(2) 0.0511(7) Uani 1 1 d .
C3 C -0.8752(3) -0.0877(4) -0.1942(2) 0.0212(5) Uani 1 1 d .
H3 H -0.9149 0.0188 -0.1532 0.025 Uiso 1 1 calc R
N2 N -0.8942(2) -0.3180(4) -0.04386(19) 0.0286(6) Uani 1 1 d .
C1 C -1.0715(3) -0.0608(4) -0.3326(2) 0.0241(6) Uani 1 1 d .
H1 H -1.0887 -0.0611 -0.4092 0.029 Uiso 1 1 calc R
C4 C -0.9338(3) -0.2889(4) -0.1600(2) 0.0232(6) Uani 1 1 d .
H4 H -0.8961 -0.3978 -0.2006 0.028 Uiso 1 1 calc R
C11 C -0.7270(3) -0.0793(4) -0.1702(2) 0.0253(6) Uani 1 1 d .
C6 C -1.1220(3) -0.2620(4) -0.2916(2) 0.0272(6) Uani 1 1 d .
H6A H -1.2170 -0.2651 -0.3014 0.033 Uiso 1 1 calc R
H6B H -1.0873 -0.3705 -0.3330 0.033 Uiso 1 1 calc R
C5 C -1.0829(3) -0.2971(5) -0.1751(2) 0.0280(6) Uani 1 1 d .
H5A H -1.1219 -0.1946 -0.1324 0.034 Uiso 1 1 calc R
H5B H -1.1145 -0.4273 -0.1532 0.034 Uiso 1 1 calc R
C2 C -0.9193(3) -0.0536(4) -0.3121(2) 0.0221(6) Uani 1 1 d .
C7 C -1.1474(3) 0.1172(4) -0.2895(2) 0.0287(7) Uani 1 1 d .
H7A H -1.1681 0.0902 -0.2172 0.034 Uiso 1 1 calc R
H7B H -1.0933 0.2371 -0.2899 0.034 Uiso 1 1 calc R
C12 C -0.6724(3) 0.0824(6) -0.1155(2) 0.0350(7) Uani 1 1 d .
H12 H -0.7263 0.1847 -0.0927 0.042 Uiso 1 1 calc R
C16 C -0.6440(3) -0.2339(5) -0.2002(2) 0.0313(7) Uani 1 1 d .
H16 H -0.6794 -0.3462 -0.2349 0.038 Uiso 1 1 calc R
C13 C -0.5358(3) 0.0934(6) -0.0940(3) 0.0453(9) Uani 1 1 d .
H13 H -0.4993 0.2031 -0.0577 0.054 Uiso 1 1 calc R
C9 C -1.4396(3) 0.3958(6) -0.4054(3) 0.0443(9) Uani 1 1 d .
H9A H -1.4312 0.3507 -0.4774 0.053 Uiso 1 1 calc R
H9B H -1.4481 0.5410 -0.4061 0.053 Uiso 1 1 calc R
C17 C -0.8536(3) -0.1929(5) -0.3896(2) 0.0295(6) Uani 1 1 d .
H17A H -0.7611 -0.1650 -0.3882 0.044 Uiso 1 1 calc R
H17B H -0.8915 -0.1708 -0.4595 0.044 Uiso 1 1 calc R
H17C H -0.8670 -0.3303 -0.3697 0.044 Uiso 1 1 calc R
C8 C -1.2731(3) 0.1521(5) -0.3559(3) 0.0340(7) Uani 1 1 d .
C15 C -0.5096(3) -0.2216(6) -0.1790(2) 0.0419(8) Uani 1 1 d .
H15 H -0.4554 -0.3247 -0.2003 0.050 Uiso 1 1 calc R
C10 C -1.5591(3) 0.3042(7) -0.3622(3) 0.0514(9) Uani 1 1 d .
H10A H -1.5629 0.3393 -0.2891 0.077 Uiso 1 1 calc R
H10B H -1.5551 0.1606 -0.3690 0.077 Uiso 1 1 calc R
H10C H -1.6361 0.3538 -0.4006 0.077 Uiso 1 1 calc R
C14 C -0.4563(3) -0.0594(6) -0.1271(3) 0.0456(9) Uani 1 1 d .
H14 H -0.3658 -0.0516 -0.1140 0.055 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 N1 O4 123.4(3)
O3 N1 C2 117.7(2)
O4 N1 C2 118.8(2)
C8 O1 C9 116.6(3)
C11 C3 C4 111.8(2)
C11 C3 C2 114.7(2)
C4 C3 C2 107.6(2)
O6 N2 O5 123.6(2)
O6 N2 C4 118.1(2)
O5 N2 C4 118.3(2)
C7 C1 C6 111.6(2)
C7 C1 C2 115.7(2)
C6 C1 C2 108.6(2)
N2 C4 C5 109.2(2)
N2 C4 C3 107.4(2)
C5 C4 C3 113.3(2)
C12 C11 C16 118.4(3)
C12 C11 C3 119.8(3)
C16 C11 C3 121.7(2)
C5 C6 C1 112.7(2)
C4 C5 C6 108.9(2)
N1 C2 C17 105.7(2)
N1 C2 C3 108.7(2)
C17 C2 C3 114.6(2)
N1 C2 C1 104.3(2)
C17 C2 C1 109.8(2)
C3 C2 C1 112.9(2)
C8 C7 C1 110.3(2)
C11 C12 C13 120.4(3)
C15 C16 C11 120.7(3)
C14 C13 C12 119.6(3)
O1 C9 C10 110.1(3)
O2 C8 O1 123.1(3)
O2 C8 C7 125.8(3)
O1 C8 C7 111.0(3)
C14 C15 C16 120.4(3)
C15 C14 C13 120.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O6 N2 1.213(3)
O4 N1 1.232(3)
O5 N2 1.222(3)
N1 O3 1.212(3)
N1 C2 1.532(4)
O1 C8 1.343(4)
O1 C9 1.484(4)
O2 C8 1.192(4)
C3 C11 1.526(4)
C3 C4 1.538(4)
C3 C2 1.556(4)
N2 C4 1.521(3)
C1 C7 1.532(4)
C1 C6 1.535(4)
C1 C2 1.560(4)
C4 C5 1.522(4)
C11 C12 1.382(4)
C11 C16 1.398(4)
C6 C5 1.530(4)
C2 C17 1.533(4)
C7 C8 1.514(4)
C12 C13 1.406(5)
C16 C15 1.384(4)
C13 C14 1.380(5)
C9 C10 1.493(5)
C15 C14 1.362(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139042733
