#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229151.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2229151
loop_
_publ_author_name
'Zhang, Dawei'
'Xu, Xianxiu'
'Liu, Qun'
_publ_section_title
;
 Ethyl 1-formamido-4-oxo-2,6-diphenylcyclohexanecarboxylate
;
_journal_coeditor_code           NC2214
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o401
_journal_paper_doi               10.1107/S1600536811000985
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C22 H23 N O4'
_chemical_formula_moiety         'C22 H23 N O4'
_chemical_formula_sum            'C22 H23 N O4'
_chemical_formula_weight         365.41
_chemical_name_systematic
;
Ethyl 1-formamido-4-oxo-2,6-diphenylcyclohexanecarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.149(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3240(12)
_cell_length_b                   13.5100(15)
_cell_length_c                   12.5870(14)
_cell_measurement_reflns_used    132
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      1.33
_cell_volume                     1901.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11361
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.190
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4439
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0415
_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)+(0.0534P)²+0.3060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                3120
_reflns_number_total             4439
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            nc2214.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229151
_cod_database_fobs_code          2229151
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 1.03050(10) 0.14890(8) 0.47576(8) 0.0541(3) Uani d . 1 . .
O O1 0.94334(8) 0.26361(7) 0.36180(7) 0.0426(2) Uani d . 1 . .
C C19 0.98394(11) 0.17327(10) 0.38744(10) 0.0364(3) Uani d . 1 . .
N N1 1.01302(10) 0.00919(8) 0.33120(9) 0.0401(3) Uani d . 1 . .
C C8 0.95919(11) 0.10312(9) 0.29070(10) 0.0339(3) Uani d . 1 . .
C C1 0.75462(12) 0.08726(11) 0.35380(11) 0.0416(3) Uani d . 1 . .
O O4 0.95020(11) -0.09967(8) 0.19437(10) 0.0637(3) Uani d . 1 . .
O O3 0.76178(11) 0.15572(10) -0.01954(9) 0.0699(4) Uani d . 1 . .
C C7 0.81977(11) 0.09052(10) 0.25754(10) 0.0366(3) Uani d . 1 . .
H H7 0.8083 0.0251 0.2239 0.044 Uiso calc R 1 . .
C C10 0.94777(13) 0.11160(11) 0.08583(11) 0.0443(3) Uani d . 1 . .
H H10A 0.9870 0.1368 0.0283 0.053 Uiso calc R 1 . .
H H10B 0.9497 0.0399 0.0832 0.053 Uiso calc R 1 . .
C C13 1.14993(12) 0.13184(11) 0.20876(11) 0.0408(3) Uani d . 1 . .
C C9 1.01555(12) 0.14705(10) 0.19429(10) 0.0378(3) Uani d . 1 . .
H H9 1.0031 0.2188 0.1961 0.045 Uiso calc R 1 . .
C C12 0.76820(13) 0.16456(11) 0.17030(11) 0.0448(3) Uani d . 1 . .
H H12A 0.6819 0.1579 0.1554 0.054 Uiso calc R 1 . .
H H12B 0.7870 0.2315 0.1955 0.054 Uiso calc R 1 . .
C C20 0.94851(15) 0.33379(11) 0.45037(13) 0.0534(4) Uani d . 1 . .
H H20A 1.0308 0.3516 0.4773 0.064 Uiso calc R 1 . .
H H20B 0.9137 0.3050 0.5088 0.064 Uiso calc R 1 . .
C C11 0.81977(13) 0.14617(11) 0.06898(11) 0.0456(3) Uani d . 1 . .
C C18 1.20075(13) 0.04802(12) 0.17129(12) 0.0510(4) Uani d . 1 . .
H H18 1.1518 0.0000 0.1342 0.061 Uiso calc R 1 . .
C C14 1.22578(14) 0.20301(12) 0.26263(12) 0.0496(4) Uani d . 1 . .
H H14 1.1936 0.2601 0.2878 0.060 Uiso calc R 1 . .
C C2 0.70022(14) 0.16996(13) 0.38990(13) 0.0550(4) Uani d . 1 . .
H H2 0.7006 0.2295 0.3528 0.066 Uiso calc R 1 . .
C C6 0.74950(14) -0.00068(14) 0.40968(14) 0.0563(4) Uani d . 1 . .
H H6 0.7837 -0.0576 0.3861 0.068 Uiso calc R 1 . .
C C22 1.00363(14) -0.07956(11) 0.28331(14) 0.0500(4) Uani d . 1 . .
H H22 1.0424 -0.1318 0.3225 0.060 Uiso calc R 1 . .
C C15 1.34882(15) 0.18981(14) 0.27916(14) 0.0610(5) Uani d . 1 . .
H H15 1.3985 0.2380 0.3152 0.073 Uiso calc R 1 . .
C C17 1.32359(15) 0.03502(15) 0.18842(14) 0.0621(5) Uani d . 1 . .
H H17 1.3564 -0.0218 0.1633 0.075 Uiso calc R 1 . .
C C16 1.39736(15) 0.10596(16) 0.24257(14) 0.0648(5) Uani d . 1 . .
H H16 1.4798 0.0970 0.2542 0.078 Uiso calc R 1 . .
C C3 0.64542(17) 0.16480(18) 0.48052(17) 0.0773(6) Uani d . 1 . .
H H3 0.6105 0.2212 0.5044 0.093 Uiso calc R 1 . .
C C5 0.69387(18) -0.00491(19) 0.50051(17) 0.0799(6) Uani d . 1 . .
H H5 0.6919 -0.0642 0.5378 0.096 Uiso calc R 1 . .
C C21 0.87950(17) 0.42237(12) 0.40695(16) 0.0659(5) Uani d . 1 . .
H H21A 0.8803 0.4706 0.4631 0.099 Uiso calc R 1 . .
H H21B 0.7984 0.4036 0.3803 0.099 Uiso calc R 1 . .
H H21C 0.9151 0.4502 0.3494 0.099 Uiso calc R 1 . .
C C4 0.64203(19) 0.0781(2) 0.53508(17) 0.0882(7) Uani d . 1 . .
H H4 0.6046 0.0753 0.5957 0.106 Uiso calc R 1 . .
H H1N 1.0524 0.0128 0.3939 0.106 Uiso d R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C19 O1 C20 . . 116.26(10) ?
O2 C19 O1 . . 124.27(12) ?
O2 C19 C8 . . 124.39(12) ?
O1 C19 C8 . . 111.30(10) ?
C22 N1 C8 . . 128.38(12) ?
C22 N1 H1N . . 117.8 ?
C8 N1 H1N . . 113.8 ?
N1 C8 C19 . . 104.24(10) ?
N1 C8 C9 . . 113.44(11) ?
C19 C8 C9 . . 109.50(10) ?
N1 C8 C7 . . 110.03(10) ?
C19 C8 C7 . . 109.02(10) ?
C9 C8 C7 . . 110.37(10) ?
C6 C1 C2 . . 117.88(15) ?
C6 C1 C7 . . 119.68(13) ?
C2 C1 C7 . . 122.44(13) ?
C1 C7 C12 . . 114.43(11) ?
C1 C7 C8 . . 112.68(10) ?
C12 C7 C8 . . 111.78(11) ?
C1 C7 H7 . . 105.7 ?
C12 C7 H7 . . 105.7 ?
C8 C7 H7 . . 105.7 ?
C11 C10 C9 . . 111.29(12) ?
C11 C10 H10A . . 109.4 ?
C9 C10 H10A . . 109.4 ?
C11 C10 H10B . . 109.4 ?
C9 C10 H10B . . 109.4 ?
H10A C10 H10B . . 108.0 ?
C18 C13 C14 . . 118.20(14) ?
C18 C13 C9 . . 122.16(12) ?
C14 C13 C9 . . 119.63(13) ?
C13 C9 C10 . . 114.53(11) ?
C13 C9 C8 . . 112.22(11) ?
C10 C9 C8 . . 111.21(11) ?
C13 C9 H9 . . 106.1 ?
C10 C9 H9 . . 106.1 ?
C8 C9 H9 . . 106.1 ?
C11 C12 C7 . . 110.16(12) ?
C11 C12 H12A . . 109.6 ?
C7 C12 H12A . . 109.6 ?
C11 C12 H12B . . 109.6 ?
C7 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
O1 C20 C21 . . 106.74(12) ?
O1 C20 H20A . . 110.4 ?
C21 C20 H20A . . 110.4 ?
O1 C20 H20B . . 110.4 ?
C21 C20 H20B . . 110.4 ?
H20A C20 H20B . . 108.6 ?
O3 C11 C12 . . 122.48(14) ?
O3 C11 C10 . . 122.25(14) ?
C12 C11 C10 . . 115.24(12) ?
C17 C18 C13 . . 120.78(15) ?
C17 C18 H18 . . 119.6 ?
C13 C18 H18 . . 119.6 ?
C15 C14 C13 . . 120.78(16) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C3 C2 C1 . . 120.67(18) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C1 C6 C5 . . 120.85(18) ?
C1 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
O4 C22 N1 . . 127.38(14) ?
O4 C22 H22 . . 116.3 ?
N1 C22 H22 . . 116.3 ?
C16 C15 C14 . . 120.19(15) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C16 C17 C18 . . 120.25(17) ?
C16 C17 H17 . . 119.9 ?
C18 C17 H17 . . 119.9 ?
C15 C16 C17 . . 119.80(16) ?
C15 C16 H16 . . 120.1 ?
C17 C16 H16 . . 120.1 ?
C4 C3 C2 . . 120.76(19) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
C4 C5 C6 . . 120.05(19) ?
C4 C5 H5 . . 120.0 ?
C6 C5 H5 . . 120.0 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C3 C4 C5 . . 119.78(19) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C19 . 1.1983(15) ?
O1 C19 . 1.3258(16) ?
O1 C20 . 1.4575(16) ?
C19 C8 . 1.5333(18) ?
N1 C22 . 1.3386(19) ?
N1 C8 . 1.4639(16) ?
N1 H1N . 0.8440 ?
C8 C9 . 1.5744(18) ?
C8 C7 . 1.5768(17) ?
C1 C6 . 1.387(2) ?
C1 C2 . 1.387(2) ?
C1 C7 . 1.5161(19) ?
O4 C22 . 1.2157(19) ?
O3 C11 . 1.2070(17) ?
C7 C12 . 1.5308(18) ?
C7 H7 . 0.9800 ?
C10 C11 . 1.505(2) ?
C10 C9 . 1.5326(18) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C13 C18 . 1.386(2) ?
C13 C14 . 1.392(2) ?
C13 C9 . 1.5176(19) ?
C9 H9 . 0.9800 ?
C12 C11 . 1.505(2) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C20 C21 . 1.485(2) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C18 C17 . 1.384(2) ?
C18 H18 . 0.9300 ?
C14 C15 . 1.387(2) ?
C14 H14 . 0.9300 ?
C2 C3 . 1.384(3) ?
C2 H2 . 0.9300 ?
C6 C5 . 1.391(3) ?
C6 H6 . 0.9300 ?
C22 H22 . 0.9300 ?
C15 C16 . 1.370(3) ?
C15 H15 . 0.9300 ?
C17 C16 . 1.378(2) ?
C17 H17 . 0.9300 ?
C16 H16 . 0.9300 ?
C3 C4 . 1.361(3) ?
C3 H3 . 0.9300 ?
C5 C4 . 1.369(3) ?
C5 H5 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C4 H4 . 0.9300 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C20 O1 C19 O2 . . . . -5.0(2) ?
C20 O1 C19 C8 . . . . 172.73(12) ?
C22 N1 C8 C19 . . . . 170.75(13) ?
C22 N1 C8 C9 . . . . -70.21(17) ?
C22 N1 C8 C7 . . . . 53.98(18) ?
O2 C19 C8 N1 . . . . -4.36(18) ?
O1 C19 C8 N1 . . . . 177.89(10) ?
O2 C19 C8 C9 . . . . -126.04(14) ?
O1 C19 C8 C9 . . . . 56.21(14) ?
O2 C19 C8 C7 . . . . 113.11(14) ?
O1 C19 C8 C7 . . . . -64.64(14) ?
C6 C1 C7 C12 . . . . 148.86(13) ?
C2 C1 C7 C12 . . . . -31.95(18) ?
C6 C1 C7 C8 . . . . -81.98(16) ?
C2 C1 C7 C8 . . . . 97.21(15) ?
N1 C8 C7 C1 . . . . 76.19(13) ?
C19 C8 C7 C1 . . . . -37.55(14) ?
C9 C8 C7 C1 . . . . -157.86(11) ?
N1 C8 C7 C12 . . . . -153.29(11) ?
C19 C8 C7 C12 . . . . 92.97(13) ?
C9 C8 C7 C12 . . . . -27.35(14) ?
C18 C13 C9 C10 . . . . -38.46(19) ?
C14 C13 C9 C10 . . . . 142.52(14) ?
C18 C13 C9 C8 . . . . 89.57(16) ?
C14 C13 C9 C8 . . . . -89.45(15) ?
C11 C10 C9 C13 . . . . -169.26(12) ?
C11 C10 C9 C8 . . . . 62.20(15) ?
N1 C8 C9 C13 . . . . -38.62(15) ?
C19 C8 C9 C13 . . . . 77.35(13) ?
C7 C8 C9 C13 . . . . -162.62(11) ?
N1 C8 C9 C10 . . . . 91.15(13) ?
C19 C8 C9 C10 . . . . -152.88(11) ?
C7 C8 C9 C10 . . . . -32.86(15) ?
C1 C7 C12 C11 . . . . -167.17(11) ?
C8 C7 C12 C11 . . . . 63.22(14) ?
C19 O1 C20 C21 . . . . -169.98(13) ?
C7 C12 C11 O3 . . . . 143.48(15) ?
C7 C12 C11 C10 . . . . -34.51(16) ?
C9 C10 C11 O3 . . . . 155.50(14) ?
C9 C10 C11 C12 . . . . -26.50(17) ?
C14 C13 C18 C17 . . . . 0.9(2) ?
C9 C13 C18 C17 . . . . -178.16(15) ?
C18 C13 C14 C15 . . . . -0.6(2) ?
C9 C13 C14 C15 . . . . 178.47(14) ?
C6 C1 C2 C3 . . . . 1.6(2) ?
C7 C1 C2 C3 . . . . -177.59(14) ?
C2 C1 C6 C5 . . . . -1.5(2) ?
C7 C1 C6 C5 . . . . 177.76(15) ?
C8 N1 C22 O4 . . . . 2.0(3) ?
C13 C14 C15 C16 . . . . -0.1(2) ?
C13 C18 C17 C16 . . . . -0.5(3) ?
C14 C15 C16 C17 . . . . 0.5(3) ?
C18 C17 C16 C15 . . . . -0.3(3) ?
C1 C2 C3 C4 . . . . -1.1(3) ?
C1 C6 C5 C4 . . . . 0.8(3) ?
C2 C3 C4 C5 . . . . 0.4(3) ?
C6 C5 C4 C3 . . . . -0.2(3) ?
