#------------------------------------------------------------------------------
#$Date: 2016-03-26 02:38:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180149 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/46/7104692.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_7104692
loop_
_publ_author_name
'Yunfeng Chen'
'Cheng Zhong'
'Xiaohua Sun'
'Novruz G. Akhmedov'
'Jeffrey L. Petersen'
'Xiaodong Shi'
_publ_section_title
;
 One-pot cascade Michael--Michael--Aldol condensation for
 diastereoselective synthesis of nitro-substituted cyclohexanes
;
_journal_name_full               'Chem. Commun.'
_journal_page_first              5150
_journal_page_last               5152
_journal_paper_doi               10.1039/b909766j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C15 H15 N O2'
_chemical_formula_weight         241.28
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.478(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6259(5)
_cell_length_b                   12.9816(10)
_cell_length_c                   14.3547(11)
_cell_measurement_reflns_used    5949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.88
_cell_volume                     1214.13(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_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  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7958
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   semi-empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0482
_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)+(0.0649P)²+0.2069P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1358
_reflns_number_gt                2339
_reflns_number_total             2705
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b909766j.txt
_cod_data_source_block           ms94ccd
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7104692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4339(2) 0.69850(10) 0.32853(8) 0.0695(4) Uani 1 1 d . . .
O2 O 0.62167(17) 0.85409(9) 0.47488(9) 0.0650(3) Uani 1 1 d . . .
N1 N 0.35405(16) 0.73982(8) 0.47422(7) 0.0392(3) Uani 1 1 d . . .
C1 C 0.19482(17) 0.71723(9) 0.53112(8) 0.0345(3) Uani 1 1 d . . .
C2 C 0.0130(2) 0.68115(11) 0.45413(9) 0.0447(3) Uani 1 1 d . . .
H2A H -0.0650 0.6274 0.4784 0.054 Uiso 1 1 calc R . .
H2B H -0.0780 0.7381 0.4322 0.054 Uiso 1 1 calc R . .
C3 C 0.1155(3) 0.64027(12) 0.37440(10) 0.0554(4) Uani 1 1 d . . .
H3A H 0.1349 0.5663 0.3801 0.066 Uiso 1 1 calc R . .
H3B H 0.0317 0.6552 0.3132 0.066 Uiso 1 1 calc R . .
C4 C 0.3192(2) 0.69418(11) 0.38449(9) 0.0474(3) Uani 1 1 d . . .
C5 C 0.4785(2) 0.82268(11) 0.50794(10) 0.0438(3) Uani 1 1 d . . .
C6 C 0.3962(2) 0.86598(11) 0.59116(10) 0.0463(3) Uani 1 1 d . . .
H6A H 0.3930 0.9407 0.5890 0.056 Uiso 1 1 calc R . .
H6B H 0.4798 0.8443 0.6505 0.056 Uiso 1 1 calc R . .
C7 C 0.17922(19) 0.82191(10) 0.58048(9) 0.0394(3) Uani 1 1 d . . .
H7A H 0.0803 0.8666 0.5419 0.047 Uiso 1 1 calc R . .
H7B H 0.1397 0.8127 0.6418 0.047 Uiso 1 1 calc R . .
C8 C 0.26374(18) 0.62973(9) 0.60135(8) 0.0352(3) Uani 1 1 d . . .
C9 C 0.4198(2) 0.56923(12) 0.59092(10) 0.0505(3) Uani 1 1 d . . .
H9A H 0.4566 0.5144 0.6322 0.061 Uiso 1 1 calc R . .
H9B H 0.4922 0.5817 0.5423 0.061 Uiso 1 1 calc R . .
C10 C 0.14528(18) 0.61102(9) 0.67910(8) 0.0361(3) Uani 1 1 d . . .
C11 C -0.0532(2) 0.64911(11) 0.67665(10) 0.0437(3) Uani 1 1 d . . .
H11 H -0.1168 0.6869 0.6245 0.052 Uiso 1 1 calc R . .
C12 C -0.1564(2) 0.63114(12) 0.75122(11) 0.0505(4) Uani 1 1 d . . .
H12 H -0.2874 0.6579 0.7490 0.061 Uiso 1 1 calc R . .
C13 C -0.0656(2) 0.57395(12) 0.82829(10) 0.0518(4) Uani 1 1 d . . .
H13 H -0.1361 0.5610 0.8775 0.062 Uiso 1 1 calc R . .
C14 C 0.1302(2) 0.53593(12) 0.83232(10) 0.0531(4) Uani 1 1 d . . .
H14 H 0.1919 0.4972 0.8843 0.064 Uiso 1 1 calc R . .
C15 C 0.2345(2) 0.55536(11) 0.75911(9) 0.0462(3) Uani 1 1 d . . .
H15 H 0.3677 0.5307 0.7633 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C4 129.64(11) . . ?
C5 N1 C1 113.58(10) . . ?
C4 N1 C1 114.23(11) . . ?
N1 C1 C8 110.72(9) . . ?
N1 C1 C7 101.14(9) . . ?
C8 C1 C7 112.78(10) . . ?
N1 C1 C2 101.90(9) . . ?
C8 C1 C2 110.17(10) . . ?
C7 C1 C2 118.96(10) . . ?
C3 C2 C1 104.19(11) . . ?
C4 C3 C2 106.22(11) . . ?
O1 C4 N1 125.20(15) . . ?
O1 C4 C3 128.47(14) . . ?
N1 C4 C3 106.33(11) . . ?
O2 C5 N1 125.78(13) . . ?
O2 C5 C6 127.49(14) . . ?
N1 C5 C6 106.71(10) . . ?
C5 C6 C7 104.46(10) . . ?
C6 C7 C1 103.60(9) . . ?
C9 C8 C10 120.84(12) . . ?
C9 C8 C1 120.61(11) . . ?
C10 C8 C1 118.50(10) . . ?
C15 C10 C11 117.37(11) . . ?
C15 C10 C8 119.80(11) . . ?
C11 C10 C8 122.81(11) . . ?
C12 C11 C10 120.85(13) . . ?
C13 C12 C11 120.32(13) . . ?
C12 C13 C14 119.79(12) . . ?
C13 C14 C15 119.98(13) . . ?
C14 C15 C10 121.65(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2035(18) . ?
O2 C5 1.2065(16) . ?
N1 C5 1.3877(17) . ?
N1 C4 1.3983(17) . ?
N1 C1 1.4763(14) . ?
C1 C8 1.5322(17) . ?
C1 C7 1.5446(16) . ?
C1 C2 1.5515(17) . ?
C2 C3 1.528(2) . ?
C3 C4 1.504(2) . ?
C5 C6 1.5090(18) . ?
C6 C7 1.5289(18) . ?
C8 C9 1.3283(18) . ?
C8 C10 1.4965(15) . ?
C10 C15 1.3943(18) . ?
C10 C11 1.3993(18) . ?
C11 C12 1.3908(18) . ?
C12 C13 1.377(2) . ?
C13 C14 1.379(2) . ?
C14 C15 1.3823(18) . ?
