#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202502.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_2202502
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1538
_journal_page_last  o1540
_publ_section_title
;
Structure of piperidine derivatives. I.
2,6-bis-(4-methylphenyl)-3-phenylpiperidin-4-one at 105 K
;
loop_
_publ_author_name
  'Subha Nandhini, M.'
  'M. Srinivasan'
  'R. V. Krishnakumar'
  'A. Mostad'
  'S. Perumal'
  'S. Selvaraj'
  'S. Natarajan'
_chemical_name_common  '2,6-bis-4-(methylphenyl)-3-phenyl-pipridin-4-one'
_chemical_formula_moiety  'C25 H25 N O'
_chemical_formula_sum  'C25 H25 N O'
_chemical_formula_weight  355.46
_chemical_melting_point  '421 K'
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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'
_cell_length_a  15.214(3)
_cell_length_b  8.7408(17)
_cell_length_c  14.885(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.75(3)
_cell_angle_gamma  90.00
_cell_volume  1979.3(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  105(2)
_exptl_crystal_density_diffrn  1.193
_diffrn_ambient_temperature  105(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
  O1 0.09037(6) 1.15516(13) 0.52459(6) 0.0295(3) Uani d . 1 . . O
  N1 0.12094(7) 0.99792(14) 0.27174(8) 0.0219(3) Uani d . 1 . . N
  H1N 0.1199(11) 0.926(2) 0.2287(12) 0.028(4) Uiso d . 1 . . H
  C2 0.19045(8) 0.96257(15) 0.33779(9) 0.0196(3) Uani d . 1 . . C
  H2 0.1773 0.8650 0.3671 0.023 Uiso calc R 1 . . H
  C3 0.19460(8) 1.09181(15) 0.40986(8) 0.0188(3) Uani d . 1 . . C
  H3 0.2161 1.1836 0.3794 0.023 Uiso calc R 1 . . H
  C4 0.10351(8) 1.13115(14) 0.44570(9) 0.0201(3) Uani d . 1 . . C
  C5 0.03162(8) 1.14327(15) 0.37540(9) 0.0213(3) Uani d . 1 . . C
  H5A 0.0391 1.2369 0.3414 0.026 Uiso calc R 1 . . H
  H5B -0.0249 1.1480 0.4046 0.026 Uiso calc R 1 . . H
  C6 0.03293(8) 1.00558(15) 0.31091(9) 0.0202(3) Uani d . 1 . . C
  H6 0.0222 0.9118 0.3451 0.024 Uiso calc R 1 . . H
  C7 -0.03677(8) 1.02044(15) 0.23744(9) 0.0207(3) Uani d . 1 . . C
  C8 -0.12295(9) 0.97475(16) 0.25459(10) 0.0243(3) Uani d . 1 . . C
  H8 -0.1377 0.9408 0.3117 0.029 Uiso calc R 1 . . H
  C9 -0.18695(9) 0.97966(16) 0.18694(10) 0.0255(3) Uani d . 1 . . C
  H9 -0.2443 0.9511 0.1999 0.031 Uiso calc R 1 . . H
  C10 -0.16673(9) 1.02660(15) 0.10005(10) 0.0243(3) Uani d . 1 . . C
  C11 -0.23384(10) 1.01837(18) 0.02469(11) 0.0325(3) Uani d . 1 . . C
  H11A -0.2246 0.9270 -0.0097 0.049 Uiso calc R 1 . . H
  H11B -0.2278 1.1062 -0.0135 0.049 Uiso calc R 1 . . H
  H11C -0.2918 1.0167 0.0493 0.049 Uiso calc R 1 . . H
  C12 -0.08107(9) 1.07638(16) 0.08426(10) 0.0253(3) Uani d . 1 . . C
  H12 -0.0665 1.1110 0.0273 0.030 Uiso calc R 1 . . H
  C13 -0.01697(9) 1.07544(15) 0.15180(9) 0.0233(3) Uani d . 1 . . C
  H13 0.0392 1.1115 0.1400 0.028 Uiso calc R 1 . . H
  C14 0.27794(8) 0.95018(15) 0.29014(9) 0.0201(3) Uani d . 1 . . C
  C15 0.29775(9) 1.04761(16) 0.21899(9) 0.0245(3) Uani d . 1 . . C
  H15 0.2568 1.1205 0.2004 0.029 Uiso calc R 1 . . H
  C16 0.37798(9) 1.03716(18) 0.17540(10) 0.0284(3) Uani d . 1 . . C
  H16 0.3897 1.1025 0.1277 0.034 Uiso calc R 1 . . H
  C17 0.44086(9) 0.93007(18) 0.20232(10) 0.0279(3) Uani d . 1 . . C
  C18 0.52667(10) 0.9138(2) 0.15290(13) 0.0426(4) Uani d . 1 . . C
  H18A 0.5702 0.8697 0.1923 0.064 Uiso calc R 1 . . H
  H18B 0.5461 1.0128 0.1335 0.064 Uiso calc R 1 . . H
  H18C 0.5181 0.8487 0.1016 0.064 Uiso calc R 1 . . H
  C19 0.42182(9) 0.83518(17) 0.27457(10) 0.0273(3) Uani d . 1 . . C
  H19 0.4635 0.7646 0.2944 0.033 Uiso calc R 1 . . H
  C20 0.34135(9) 0.84430(16) 0.31762(9) 0.0234(3) Uani d . 1 . . C
  H20 0.3297 0.7790 0.3653 0.028 Uiso calc R 1 . . H
  C21 0.26176(8) 1.05322(15) 0.48246(8) 0.0196(3) Uani d . 1 . . C
  C22 0.34282(9) 1.12744(16) 0.48517(9) 0.0245(3) Uani d . 1 . . C
  H22 0.3540 1.2061 0.4448 0.029 Uiso calc R 1 . . H
  C23 0.40729(9) 1.08526(18) 0.54762(10) 0.0294(3) Uani d . 1 . . C
  H23 0.4611 1.1356 0.5487 0.035 Uiso calc R 1 . . H
  C24 0.39130(10) 0.96833(18) 0.60814(10) 0.0304(3) Uani d . 1 . . C
  H24 0.4344 0.9399 0.6498 0.036 Uiso calc R 1 . . H
  C25 0.31059(10) 0.89373(18) 0.60640(10) 0.0290(3) Uani d . 1 . . C
  H25 0.2996 0.8154 0.6470 0.035 Uiso calc R 1 . . H
  C26 0.24649(9) 0.93610(16) 0.54405(9) 0.0237(3) Uani d . 1 . . C
  H26 0.1926 0.8858 0.5433 0.028 Uiso calc R 1 . . 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
  O1 0.0289(5) 0.0396(6) 0.0200(5) 0.0080(4) 0.0029(4) -0.0032(4)
  N1 0.0183(5) 0.0285(6) 0.0189(5) 0.0026(5) 0.0004(4) -0.0054(5)
  C2 0.0189(6) 0.0199(6) 0.0198(6) 0.0013(5) 0.0011(5) -0.0003(5)
  C3 0.0196(6) 0.0187(6) 0.0180(6) -0.0005(5) 0.0015(5) 0.0011(5)
  C4 0.0230(6) 0.0169(6) 0.0205(6) 0.0006(5) 0.0027(5) 0.0002(5)
  C5 0.0199(6) 0.0224(6) 0.0216(6) 0.0027(5) 0.0024(5) -0.0010(5)
  C6 0.0190(6) 0.0203(6) 0.0213(6) 0.0003(5) 0.0021(5) -0.0005(5)
  C7 0.0201(6) 0.0188(6) 0.0230(7) 0.0013(5) 0.0005(5) -0.0038(5)
  C8 0.0224(7) 0.0268(7) 0.0237(7) 0.0000(5) 0.0030(5) -0.0038(5)
  C9 0.0186(6) 0.0264(7) 0.0314(8) -0.0003(5) 0.0015(5) -0.0052(6)
  C10 0.0254(7) 0.0179(6) 0.0293(7) 0.0039(5) -0.0061(5) -0.0037(5)
  C11 0.0321(8) 0.0296(8) 0.0356(8) 0.0008(6) -0.0107(6) -0.0005(6)
  C12 0.0289(7) 0.0225(7) 0.0243(7) 0.0023(5) -0.0001(5) 0.0025(5)
  C13 0.0206(6) 0.0215(6) 0.0279(7) -0.0004(5) 0.0012(5) 0.0010(5)
  C14 0.0185(6) 0.0232(6) 0.0186(6) -0.0002(5) -0.0004(5) -0.0055(5)
  C15 0.0220(7) 0.0279(7) 0.0238(7) 0.0024(5) 0.0011(5) -0.0001(5)
  C16 0.0272(7) 0.0343(8) 0.0239(7) -0.0034(6) 0.0045(6) -0.0011(6)
  C17 0.0194(6) 0.0346(8) 0.0297(7) -0.0034(6) 0.0034(5) -0.0136(6)
  C18 0.0268(8) 0.0513(10) 0.0502(10) -0.0015(7) 0.0141(7) -0.0149(8)
  C19 0.0202(6) 0.0303(7) 0.0313(7) 0.0046(5) -0.0047(5) -0.0100(6)
  C20 0.0233(6) 0.0253(7) 0.0217(6) 0.0020(5) -0.0021(5) -0.0028(5)
  C21 0.0198(6) 0.0218(6) 0.0173(6) 0.0022(5) 0.0010(5) -0.0029(5)
  C22 0.0249(7) 0.0236(7) 0.0250(7) -0.0017(5) 0.0013(5) -0.0013(5)
  C23 0.0229(7) 0.0312(7) 0.0339(8) -0.0014(6) -0.0034(6) -0.0069(6)
  C24 0.0286(7) 0.0359(8) 0.0265(7) 0.0072(6) -0.0080(6) -0.0041(6)
  C25 0.0325(8) 0.0314(7) 0.0232(7) 0.0048(6) 0.0000(6) 0.0047(6)
  C26 0.0221(7) 0.0265(7) 0.0226(7) 0.0003(5) 0.0019(5) 0.0011(5)
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
  O1 C4 . 1.2120(16) yes
  N1 C2 . 1.4675(17) yes
  N1 C6 . 1.4689(17) yes
  N1 H1N . 0.895(18) ?
  C2 C14 . 1.5202(18) ?
  C2 C3 . 1.5586(18) yes
  C2 H2 . 0.98 ?
  C3 C21 . 1.5154(17) ?
  C3 C4 . 1.5306(18) yes
  C3 H3 . 0.98 ?
  C4 C5 . 1.5075(18) yes
  C5 C6 . 1.5398(18) yes
  C5 H5A . 0.97 ?
  C5 H5B . 0.97 ?
  C6 C7 . 1.5188(18) ?
  C6 H6 . 0.98 ?
  C7 C8 . 1.3974(19) ?
  C7 C13 . 1.3989(19) ?
  C8 C9 . 1.392(2) ?
  C8 H8 . 0.93 ?
  C9 C10 . 1.395(2) ?
  C9 H9 . 0.93 ?
  C10 C12 . 1.397(2) ?
  C10 C11 . 1.5087(19) ?
  C11 H11A . 0.96 ?
  C11 H11B . 0.96 ?
  C11 H11C . 0.96 ?
  C12 C13 . 1.3915(19) ?
  C12 H12 . 0.93 ?
  C13 H13 . 0.93 ?
  C14 C20 . 1.3944(19) ?
  C14 C15 . 1.3950(19) ?
  C15 C16 . 1.393(2) ?
  C15 H15 . 0.93 ?
  C16 C17 . 1.394(2) ?
  C16 H16 . 0.93 ?
  C17 C19 . 1.392(2) ?
  C17 C18 . 1.514(2) ?
  C18 H18A . 0.96 ?
  C18 H18B . 0.96 ?
  C18 H18C . 0.96 ?
  C19 C20 . 1.392(2) ?
  C19 H19 . 0.93 ?
  C20 H20 . 0.93 ?
  C21 C22 . 1.3937(19) ?
  C21 C26 . 1.3957(19) ?
  C22 C23 . 1.392(2) ?
  C22 H22 . 0.93 ?
  C23 C24 . 1.386(2) ?
  C23 H23 . 0.93 ?
  C24 C25 . 1.390(2) ?
  C24 H24 . 0.93 ?
  C25 C26 . 1.388(2) ?
  C25 H25 . 0.93 ?
  C26 H26 . 0.93 ?