#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2200868.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_2200868
loop_
_publ_author_name
'Vijayalakshmi, L.'
'Radhakrishnan, T. R'
_publ_section_title
;
 Ethyl 4-oxo-2,6-diphenylpiperidine-3-carboxylate
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o220
_journal_page_last               o221
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C20 H21 N O3'
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_weight         323.38
_chemical_name_systematic
;
Ethyl 4-oxo-2,6-diphenylpiperidine-3-carboxylate
;
_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                 100.390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.124(2)
_cell_length_b                   7.801(3)
_cell_length_c                   22.896(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_volume                     1778.6(8)
_computing_cell_refinement       'MolEN (Fair,1990)'
_computing_data_collection       'CAD-4 Software (Frenz, 1989)'
_computing_data_reduction        MolEN
_computing_molecular_graphics    'ZORTEP97 (Zsolnai, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .923
_diffrn_measured_fraction_theta_max .923
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .047
_diffrn_reflns_av_sigmaI/netI    .0146
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3430
_diffrn_reflns_theta_full        25.29
_diffrn_reflns_theta_max         25.29
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        negligible
_diffrn_standards_interval_count 60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .081
_exptl_absorpt_correction_T_max  .986
_exptl_absorpt_correction_T_min  .972
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .17
_exptl_crystal_size_min          .09
_refine_diff_density_max         .44
_refine_diff_density_min         -.41
_refine_ls_extinction_coef       .0110(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3236
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          .083
_refine_ls_R_factor_gt           .069
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.1093P)^2^+0.5001P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .185
_refine_ls_wR_factor_ref         .206
_reflns_number_gt                2629
_reflns_number_total             3236
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    ci6074.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_database_code               2200868
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_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
_atom_site_type_symbol
N1 .22618(16) .8041(2) .05357(7) .0533(5) Uani d D 1 . . N
H1 .1648(19) .874(3) .0662(10) .067(7) Uiso d D 1 . . H
C2 .35533(19) .8391(3) .09144(9) .0545(5) Uani d . 1 . . C
H2 .3805 .9584 .0858 .065 Uiso calc R 1 . . H
C3 .46244(19) .7192(3) .07300(9) .0561(6) Uani d . 1 . . C
H3 .4429 .6019 .0842 .067 Uiso calc R 1 . . H
O4 .56073(18) .7240(3) -.01393(9) .1000(8) Uani d . 1 . . O
C4 .4587(2) .7226(3) .00661(11) .0653(6) Uani d . 1 . . C
C5 .3229(2) .7190(3) -.03089(10) .0654(6) Uani d . 1 . . C
H5A .2875 .6033 -.0314 .078 Uiso calc R 1 . . H
H5B .3300 .7492 -.0713 .078 Uiso calc R 1 . . H
C6 .22469(19) .8419(3) -.00888(9) .0534(5) Uani d . 1 . . C
H6 .2553 .9600 -.0125 .064 Uiso calc R 1 . . H
C7 .0858(2) .8217(3) -.04577(9) .0540(5) Uani d . 1 . . C
C8 -.0148(2) .7309(3) -.02593(11) .0690(7) Uani d . 1 . . C
H8 .0014 .6824 .0118 .083 Uiso calc R 1 . . H
C9 -.1395(3) .7118(4) -.06175(14) .0823(8) Uani d . 1 . . C
H9 -.2066 .6517 -.0476 .099 Uiso calc R 1 . . H
C10 -.1651(3) .7796(4) -.11737(14) .0816(8) Uani d . 1 . . C
H10 -.2486 .7643 -.1415 .098 Uiso calc R 1 . . H
C11 -.0666(3) .8706(4) -.13741(13) .0852(8) Uani d . 1 . . C
H11 -.0835 .9189 -.1752 .102 Uiso calc R 1 . . H
C12 .0573(2) .8908(4) -.10199(11) .0715(7) Uani d . 1 . . C
H12 .1233 .9526 -.1163 .086 Uiso calc R 1 . . H
C13 .3464(2) .8118(3) .15574(9) .0593(6) Uani d . 1 . . C
C14 .4162(3) .9160(4) .19945(11) .0830(8) Uani d . 1 . . C
H14 .4671 1.0060 .1888 .100 Uiso calc R 1 . . H
C15 .4119(4) .8897(6) .25807(14) .1067(12) Uani d . 1 . . C
H15 .4605 .9609 .2868 .128 Uiso calc R 1 . . H
C16 .3372(4) .7603(7) .27461(13) .1133(14) Uani d . 1 . . C
H16 .3337 .7438 .3145 .136 Uiso calc R 1 . . H
C17 .2670(3) .6540(5) .23251(14) .1010(11) Uani d . 1 . . C
H17 .2160 .5649 .2438 .121 Uiso calc R 1 . . H
C18 .2719(3) .6797(4) .17266(11) .0762(7) Uani d . 1 . . C
H18 .2246 .6070 .1441 .091 Uiso calc R 1 . . H
O31 .64336(17) .9081(3) .11099(10) .0892(7) Uani d . 1 . . O
C31 .6011(2) .7650(3) .10495(11) .0673(6) Uani d . 1 . . C
O32 .67255(18) .6267(3) .12460(11) .1024(8) Uani d D 1 . . O
C32 .7934(6) .6683(10) .1695(3) .104(2) Uani d PD .55 A 1 C
H32A .7921 .6105 .2069 .125 Uiso calc PR .55 A 1 H
H32B .8025 .7908 .1763 .125 Uiso calc PR .55 A 1 H
C33 .9020(8) .5997(19) .1393(6) .253(9) Uani d PDU .55 A 1 C
H33A .9876 .6406 .1595 .379 Uiso calc PR .55 A 1 H
H33B .8870 .6379 .0988 .379 Uiso calc PR .55 A 1 H
H33C .9010 .4767 .1403 .379 Uiso calc PR .55 A 1 H
C32' .8205(5) .6432(12) .1322(4) .096(2) Uani d PD .45 A 2 C
H32C .8465 .7332 .1073 .115 Uiso calc PR .45 A 2 H
H32D .8623 .5362 .1239 .115 Uiso calc PR .45 A 2 H
C33' .8541(11) .6893(18) .1973(4) .158(5) Uani d PD .45 A 2 C
H33D .9369 .7521 .2049 .237 Uiso calc PR .45 A 2 H
H33E .8632 .5864 .2207 .237 Uiso calc PR .45 A 2 H
H33F .7834 .7586 .2077 .237 Uiso calc PR .45 A 2 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 .0440(9) .0658(11) .0518(10) .0002(8) .0135(7) -.0015(8)
C2 .0473(11) .0584(12) .0580(12) -.0022(9) .0100(9) .0005(9)
C3 .0444(11) .0628(12) .0628(12) .0005(9) .0143(9) .0060(10)
O4 .0555(10) .166(2) .0865(13) .0164(11) .0340(9) .0159(13)
C4 .0513(12) .0811(16) .0682(14) .0077(10) .0233(10) .0058(11)
C5 .0563(12) .0884(16) .0548(12) .0081(11) .0190(10) -.0010(11)
C6 .0480(11) .0597(12) .0542(11) -.0023(8) .0136(8) .0029(9)
C7 .0489(11) .0563(11) .0580(12) .0013(9) .0130(9) -.0031(9)
C8 .0554(13) .0803(16) .0724(14) -.0084(11) .0141(11) .0037(12)
C9 .0530(13) .0913(19) .102(2) -.0125(13) .0134(13) -.0056(16)
C10 .0571(14) .0824(18) .097(2) .0028(12) -.0094(13) -.0090(15)
C11 .0822(18) .093(2) .0725(16) .0014(15) -.0063(13) .0071(14)
C12 .0629(14) .0831(16) .0662(14) -.0061(12) .0058(11) .0089(12)
C13 .0523(11) .0704(14) .0549(12) .0072(10) .0089(9) -.0029(10)
C14 .0745(16) .100(2) .0703(16) .0022(14) .0024(12) -.0185(14)
C15 .107(2) .144(3) .0644(18) .020(2) .0005(16) -.0282(19)
C16 .122(3) .168(4) .0509(16) .049(3) .0182(17) .005(2)
C17 .106(2) .128(3) .0745(19) .014(2) .0326(17) .0280(19)
C18 .0809(16) .0873(18) .0622(14) -.0003(14) .0179(12) .0067(12)
O31 .0558(10) .0805(13) .1287(17) -.0132(9) .0096(10) .0093(11)
C31 .0496(12) .0720(15) .0805(16) -.0031(11) .0126(11) .0102(12)
O32 .0609(11) .0856(14) .145(2) .0002(9) -.0239(11) .0235(12)
C32 .082(4) .119(5) .096(5) .002(4) -.028(4) .010(4)
C33 .054(4) .326(17) .360(18) .010(6) -.010(6) -.234(15)
C32' .061(4) .106(6) .112(7) .016(4) -.004(4) .009(5)
C33' .101(7) .239(14) .114(7) -.045(8) -.036(6) .049(8)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .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
C6 N1 C2 . 113.26(15)
C6 N1 H1 . 107.6(14)
C2 N1 H1 (14). 106.8
N1 C2 C13 . 110.44(16)
N1 C2 C3 . 108.77(17)
C13 C2 C3 . 110.46(17)
N1 C2 H2 . 109.0
C13 C2 H2 . 109.0
C3 C2 H2 . 109.0
C31 C3 C4 . 109.62(18)
C31 C3 C2 . 111.22(18)
C4 C3 C2 . 111.82(17)
C31 C3 H3 . 108.0
C4 C3 H3 . 108.0
C2 C3 H3 . 108.0
O4 C4 C5 . 122.8(2)
O4 C4 C3 . 121.5(2)
C5 C4 C3 . 115.65(17)
C4 C5 C6 . 112.75(19)
C4 C5 H5A . 109.0
C6 C5 H5A . 109.0
C4 C5 H5B . 109.0
C6 C5 H5B . 109.0
H5A C5 H5B . 107.8
N1 C6 C7 . 111.77(16)
N1 C6 C5 . 107.68(17)
C7 C6 C5 . 110.13(17)
N1 C6 H6 . 109.1
C7 C6 H6 . 109.1
C5 C6 H6 . 109.1
C12 C7 C8 . 117.7(2)
C12 C7 C6 . 119.87(19)
C8 C7 C6 . 122.4(2)
C9 C8 C7 . 120.5(2)
C9 C8 H8 . 119.7
C7 C8 H8 . 119.7
C10 C9 C8 . 120.9(3)
C10 C9 H9 . 119.6
C8 C9 H9 . 119.6
C9 C10 C11 . 119.2(2)
C9 C10 H10 . 120.4
C11 C10 H10 . 120.4
C10 C11 C12 . 120.3(3)
C10 C11 H11 . 119.9
C12 C11 H11 . 119.9
C11 C12 C7 . 121.4(2)
C11 C12 H12 . 119.3
C7 C12 H12 . 119.3
C18 C13 C14 . 118.2(2)
C18 C13 C2 . 121.0(2)
C14 C13 C2 . 120.8(2)
C15 C14 C13 . 121.4(3)
C15 C14 H14 . 119.3
C13 C14 H14 . 119.3
C16 C15 C14 . 120.3(3)
C16 C15 H15 . 119.9
C14 C15 H15 . 119.9
C15 C16 C17 . 120.0(3)
C15 C16 H16 . 120.0
C17 C16 H16 . 120.0
C16 C17 C18 . 119.9(3)
C16 C17 H17 . 120.1
C18 C17 H17 . 120.1
C13 C18 C17 . 120.2(3)
C13 C18 H18 . 119.9
C17 C18 H18 . 119.9
O31 C31 O32 . 123.9(2)
O31 C31 C3 . 124.2(2)
O32 C31 C3 . 112.0(2)
C31 O32 C32' . 116.4(4)
C31 O32 C32 . 112.7(4)
C32' O32 C32 . 37.9(3)
O32 C32 C33 . 100.6(6)
O32 C32 H32A . 111.7
C33 C32 H32A . 111.7
O32 C32 H32B . 111.7
C33 C32 H32B . 111.7
H32A C32 H32B . 109.4
C32 C33 H33A . 109.5
C32 C33 H33B . 109.5
H33A C33 H33B . 109.5
C32 C33 H33C . 109.5
H33A C33 H33C . 109.5
H33B C33 H33C . 109.5
O32 C32' C33' . 100.3(6)
O32 C32' H32C . 111.7
C33' C32' H32C . 111.7
O32 C32' H32D . 111.7
C33' C32' H32D . 111.7
H32C C32' H32D . 109.5
C32' C33' H33D . 109.5
C32' C33' H33E . 109.5
H33D C33' H33E . 109.5
C32' C33' H33F . 109.5
H33D C33' H33F . 109.5
H33E C33' H33F . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.457(3)
N1 C2 1.458(3)
N1 H1 .91(2)
C2 C13 1.506(3)
C2 C3 1.547(3)
C2 H2 .98
C3 C31 1.505(3)
C3 C4 1.514(3)
C3 H3 .98
O4 C4 1.209(3)
C4 C5 1.485(3)
C5 C6 1.530(3)
C5 H5A .97
C5 H5B .97
C6 C7 1.512(3)
C6 H6 .98
C7 C12 1.378(3)
C7 C8 1.383(3)
C8 C9 1.383(4)
C8 H8 .93
C9 C10 1.360(4)
C9 H9 .93
C10 C11 1.370(4)
C10 H10 .93
C11 C12 1.374(3)
C11 H11 .93
C12 H12 .93
C13 C18 1.374(4)
C13 C14 1.381(3)
C14 C15 1.366(4)
C14 H14 .93
C15 C16 1.355(6)
C15 H15 .93
C16 C17 1.370(6)
C16 H16 .93
C17 C18 1.395(4)
C17 H17 .93
C18 H18 .93
O31 C31 1.194(3)
C31 O32 1.331(3)
O32 C32' 1.482(5)
O32 C32 1.485(4)
C32 C33 1.500(5)
C32 H32A .97
C32 H32B .97
C33 H33A .96
C33 H33B .96
C33 H33C .96
C32' C33' 1.512(5)
C32' H32C .97
C32' H32D .97
C33' H33D .96
C33' H33E .96
C33' H33F .96
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
_geom_torsion_publ_flag
C6 N1 C2 C13 175.15(17) yes
C6 N1 C2 C3 -63.5(2) yes
N1 C2 C3 C31 172.47(17) ?
C13 C2 C3 C31 -66.2(2) ?
N1 C2 C3 C4 49.5(2) yes
C13 C2 C3 C4 170.91(18) ?
C31 C3 C4 O4 15.0(3) ?
C2 C3 C4 O4 138.8(3) ?
C31 C3 C4 C5 -166.7(2) ?
C2 C3 C4 C5 -42.9(3) yes
O4 C4 C5 C6 -136.6(3) ?
C3 C4 C5 C6 45.1(3) yes
C2 N1 C6 C7 -174.10(17) ?
C2 N1 C6 C5 64.8(2) yes
C4 C5 C6 N1 -53.3(2) yes
C4 C5 C6 C7 -175.37(18) yes
N1 C6 C7 C12 164.2(2) ?
C5 C6 C7 C12 -76.2(3) ?
N1 C6 C7 C8 -17.7(3) ?
C5 C6 C7 C8 101.9(2) ?
C12 C7 C8 C9 -.2(4) ?
C6 C7 C8 C9 -178.3(2) ?
C7 C8 C9 C10 .9(4) ?
C8 C9 C10 C11 -1.3(5) ?
C9 C10 C11 C12 1.0(5) ?
C10 C11 C12 C7 -.3(4) ?
C8 C7 C12 C11 -.1(4) ?
C6 C7 C12 C11 178.1(2) ?
N1 C2 C13 C18 38.2(3) ?
C3 C2 C13 C18 -82.2(3) ?
N1 C2 C13 C14 -143.7(2) ?
C3 C2 C13 C14 95.9(3) ?
C18 C13 C14 C15 .0(4) ?
C2 C13 C14 C15 -178.2(2) ?
C13 C14 C15 C16 -.7(5) ?
C14 C15 C16 C17 .8(6) ?
C15 C16 C17 C18 -.3(5) ?
C14 C13 C18 C17 .5(4) ?
C2 C13 C18 C17 178.7(2) ?
C16 C17 C18 C13 -.4(5) ?
C4 C3 C31 O31 79.3(3) ?
C2 C3 C31 O31 -44.9(3) ?
C4 C3 C31 O32 -99.3(3) ?
C2 C3 C31 O32 136.5(2) ?
O31 C31 O32 C32' -24.7(6) ?
C3 C31 O32 C32' 153.9(4) ?
O31 C31 O32 C32 17.0(5) ?
C3 C31 O32 C32 -164.4(4) ?
C31 O32 C32 C33 -120.6(8) ?
C32' O32 C32 C33 -16.2(9) ?
C31 O32 C32' C33' 94.7(7) ?
C32 O32 C32' C33' 1.1(8) ?