#------------------------------------------------------------------------------
#$Date: 2010-01-30 13:59:17 +0000 (Sat, 30 Jan 2010) $
#$Revision: 966 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008909.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_2008909
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  1607
_journal_page_last  1610
_publ_section_title
;
Intermolecular N-H...N and C-H...O interactions form one-dimensional
chains comprising the two independent molecules of
N,N'-dicyclohexyl-N-nicotinoylurea.
;
loop_
_publ_author_name
  'Gallagher, John F.'
  'Kenny, Peter T.M.'
  'Sheehy, Michael J.'
_chemical_name_common  'Dicyclohexyl-N-(3-pyridinylcarbonyl)urea'
_chemical_formula_moiety  'C19 H27 N3 O2 '
_chemical_formula_sum  'C19 H27 N3 O2'
_chemical_formula_weight  329.44
_chemical_melting_point  397
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  9.6855(11)
_cell_length_b  12.775(3)
_cell_length_c  16.053(6)
_cell_angle_alpha  67.29(3)
_cell_angle_beta  87.640(17)
_cell_angle_gamma  85.750(17)
_cell_volume  1827.0(8)
_cell_formula_units_Z  4
_cell_measurement_temperature  290.0(10)
_exptl_crystal_density_diffrn  1.198
_diffrn_ambient_temperature  290.0(10)
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
  O1A 0.1679(2) 0.45362(15) 0.05891(13) 0.0787(6) Uani d . 1 . . O
  O2A -0.11745(18) 0.23155(15) 0.26862(11) 0.0629(5) Uani d . 1 . . O
  N1A 0.06425(19) 0.31661(15) 0.17443(13) 0.0436(5) Uani d . 1 . . N
  N2A 0.0470(2) 0.30341(15) 0.32298(13) 0.0474(5) Uani d . 1 . . N
  C1A 0.0928(3) 0.4268(2) 0.12541(18) 0.0500(7) Uani d . 1 . . C
  C2A -0.0117(3) 0.2812(2) 0.25913(17) 0.0461(6) Uani d . 1 . . C
  C11A 0.0243(3) 0.51589(19) 0.15515(15) 0.0428(6) Uani d . 1 . . C
  C12A -0.1172(3) 0.5342(2) 0.15768(16) 0.0515(7) Uani d . 1 . . C
  N13A -0.1811(2) 0.61515(18) 0.18150(14) 0.0584(6) Uani d . 1 . . N
  C14A -0.1003(3) 0.6798(2) 0.20356(18) 0.0628(8) Uani d . 1 . . C
  C15A 0.0409(3) 0.6699(2) 0.20185(18) 0.0610(8) Uani d . 1 . . C
  C16A 0.1035(3) 0.5871(2) 0.17609(17) 0.0523(7) Uani d . 1 . . C
  C21A 0.1072(3) 0.22852(19) 0.13835(16) 0.0474(6) Uani d . 1 . . C
  C22A -0.0036(3) 0.2128(2) 0.08194(19) 0.0720(9) Uani d . 1 . . C
  C23A 0.0487(4) 0.1246(3) 0.0434(2) 0.0952(11) Uani d . 1 . . C
  C24A 0.0935(4) 0.0124(3) 0.1178(2) 0.0906(11) Uani d . 1 . . C
  C25A 0.2025(3) 0.0288(2) 0.1748(2) 0.0744(9) Uani d . 1 . . C
  C26A 0.1530(3) 0.1170(2) 0.21272(17) 0.0555(7) Uani d . 1 . . C
  C31A -0.0105(3) 0.27225(19) 0.41431(15) 0.0454(6) Uani d . 1 . . C
  C32A 0.0535(3) 0.1596(2) 0.47721(16) 0.0601(8) Uani d . 1 . . C
  C33A -0.0077(3) 0.1257(2) 0.57206(17) 0.0714(9) Uani d . 1 . . C
  C34A 0.0063(3) 0.2182(3) 0.60756(19) 0.0778(9) Uani d . 1 . . C
  C35A -0.0536(3) 0.3323(3) 0.54445(19) 0.0767(9) Uani d . 1 . . C
  C36A 0.0053(3) 0.3643(2) 0.44941(17) 0.0621(8) Uani d . 1 . . C
  O1B 0.6594(2) 0.53210(14) 0.43604(13) 0.0729(6) Uani d . 1 . . O
  O2B 0.33467(18) 0.75199(14) 0.24565(11) 0.0571(5) Uani d . 1 . . O
  N1B 0.53246(19) 0.67120(15) 0.32865(12) 0.0426(5) Uani d . 1 . . N
  N2B 0.5164(2) 0.69338(15) 0.17862(13) 0.0453(5) Uani d . 1 . . N
  C1B 0.5797(3) 0.5611(2) 0.37341(17) 0.0475(6) Uani d . 1 . . C
  C2B 0.4505(3) 0.70856(19) 0.24803(17) 0.0423(6) Uani d . 1 . . C
  C11B 0.5274(3) 0.47391(19) 0.34298(15) 0.0412(6) Uani d . 1 . . C
  C12B 0.3880(3) 0.4606(2) 0.33963(16) 0.0497(7) Uani d . 1 . . C
  N13B 0.3374(2) 0.38283(18) 0.31477(14) 0.0544(6) Uani d . 1 . . N
  C14B 0.4304(3) 0.3157(2) 0.29196(17) 0.0586(7) Uani d . 1 . . C
  C15B 0.5706(3) 0.3205(2) 0.29523(17) 0.0586(7) Uani d . 1 . . C
  C16B 0.6195(3) 0.4004(2) 0.32195(16) 0.0497(7) Uani d . 1 . . C
  C21B 0.5549(3) 0.75727(19) 0.36687(16) 0.0484(7) Uani d . 1 . . C
  C22B 0.4314(3) 0.7740(2) 0.42174(17) 0.0628(8) Uani d . 1 . . C
  C23B 0.4556(4) 0.8613(3) 0.4614(2) 0.0874(10) Uani d . 1 . . C
  C24B 0.4909(4) 0.9728(3) 0.3874(2) 0.0991(13) Uani d . 1 . . C
  C25B 0.6166(4) 0.9560(2) 0.3340(2) 0.0859(11) Uani d . 1 . . C
  C26B 0.5934(3) 0.8684(2) 0.29399(17) 0.0615(8) Uani d . 1 . . C
  C31B 0.4490(2) 0.72187(19) 0.09276(15) 0.0433(6) Uani d . 1 . . C
  C32B 0.4731(3) 0.8414(2) 0.02862(17) 0.0654(8) Uani d . 1 . . C
  C33B 0.3980(3) 0.8704(2) -0.05953(18) 0.0819(10) Uani d . 1 . . C
  C34B 0.4393(3) 0.7860(3) -0.10230(18) 0.0807(10) Uani d . 1 . . C
  C35B 0.4186(4) 0.6654(2) -0.03735(19) 0.0797(10) Uani d . 1 . . C
  C36B 0.4926(3) 0.6382(2) 0.05095(18) 0.0709(9) Uani d . 1 . . C
  H2A 0.1227 0.3379 0.3101 0.057 Uiso calc R 1 . . H
  H12A -0.1714 0.4878 0.1420 0.062 Uiso calc R 1 . . H
  H14A -0.1428 0.7356 0.2214 0.075 Uiso calc R 1 . . H
  H15A 0.0929 0.7177 0.2176 0.073 Uiso calc R 1 . . H
  H16A 0.1996 0.5792 0.1728 0.063 Uiso calc R 1 . . H
  H21A 0.1876 0.2552 0.0986 0.057 Uiso calc R 1 . . H
  H22A -0.0278 0.2847 0.0330 0.086 Uiso calc R 1 . . H
  H22B -0.0859 0.1877 0.1187 0.086 Uiso calc R 1 . . H
  H23A -0.0243 0.1127 0.0090 0.114 Uiso calc R 1 . . H
  H23B 0.1264 0.1530 0.0027 0.114 Uiso calc R 1 . . H
  H24A 0.0141 -0.0195 0.1555 0.109 Uiso calc R 1 . . H
  H24B 0.1298 -0.0408 0.0914 0.109 Uiso calc R 1 . . H
  H25A 0.2856 0.0528 0.1385 0.089 Uiso calc R 1 . . H
  H25B 0.2257 -0.0429 0.2241 0.089 Uiso calc R 1 . . H
  H26A 0.0763 0.0891 0.2544 0.067 Uiso calc R 1 . . H
  H26B 0.2274 0.1293 0.2460 0.067 Uiso calc R 1 . . H
  H31A -0.1098 0.2640 0.4115 0.055 Uiso calc R 1 . . H
  H32A 0.1527 0.1646 0.4793 0.072 Uiso calc R 1 . . H
  H32B 0.0380 0.1015 0.4542 0.072 Uiso calc R 1 . . H
  H33A -0.1048 0.1121 0.5713 0.086 Uiso calc R 1 . . H
  H33B 0.0398 0.0557 0.6118 0.086 Uiso calc R 1 . . H
  H34A -0.0406 0.1976 0.6657 0.093 Uiso calc R 1 . . H
  H34B 0.1035 0.2237 0.6165 0.093 Uiso calc R 1 . . H
  H35A -0.0338 0.3898 0.5670 0.092 Uiso calc R 1 . . H
  H35B -0.1534 0.3303 0.5430 0.092 Uiso calc R 1 . . H
  H36A -0.0420 0.4343 0.4097 0.074 Uiso calc R 1 . . H
  H36B 0.1027 0.3775 0.4493 0.074 Uiso calc R 1 . . H
  H2B 0.6009 0.6660 0.1848 0.054 Uiso calc R 1 . . H
  H12B 0.3255 0.5087 0.3557 0.060 Uiso calc R 1 . . H
  H14B 0.3978 0.2623 0.2726 0.070 Uiso calc R 1 . . H
  H15B 0.6313 0.2708 0.2797 0.070 Uiso calc R 1 . . H
  H16B 0.7142 0.4049 0.3258 0.060 Uiso calc R 1 . . H
  H21B 0.6334 0.7282 0.4079 0.058 Uiso calc R 1 . . H
  H22C 0.4133 0.7021 0.4702 0.075 Uiso calc R 1 . . H
  H22D 0.3505 0.7989 0.3836 0.075 Uiso calc R 1 . . H
  H23C 0.3730 0.8733 0.4937 0.105 Uiso calc R 1 . . H
  H23D 0.5308 0.8333 0.5040 0.105 Uiso calc R 1 . . H
  H24C 0.4128 1.0036 0.3474 0.119 Uiso calc R 1 . . H
  H24D 0.5090 1.0270 0.4139 0.119 Uiso calc R 1 . . H
  H25C 0.6963 0.9307 0.3732 0.103 Uiso calc R 1 . . H
  H25D 0.6359 1.0278 0.2858 0.103 Uiso calc R 1 . . H
  H26C 0.5200 0.8973 0.2501 0.074 Uiso calc R 1 . . H
  H26D 0.6772 0.8557 0.2630 0.074 Uiso calc R 1 . . H
  H31B 0.3492 0.7175 0.1049 0.052 Uiso calc R 1 . . H
  H32C 0.5716 0.8492 0.0165 0.078 Uiso calc R 1 . . H
  H32D 0.4403 0.8943 0.0562 0.078 Uiso calc R 1 . . H
  H33C 0.2989 0.8708 -0.0481 0.098 Uiso calc R 1 . . H
  H33D 0.4195 0.9460 -0.1010 0.098 Uiso calc R 1 . . H
  H34C 0.5359 0.7927 -0.1210 0.097 Uiso calc R 1 . . H
  H34D 0.3843 0.8032 -0.1557 0.097 Uiso calc R 1 . . H
  H35C 0.4538 0.6129 -0.0647 0.096 Uiso calc R 1 . . H
  H35D 0.3204 0.6557 -0.0253 0.096 Uiso calc R 1 . . H
  H36C 0.4723 0.5624 0.0927 0.085 Uiso calc R 1 . . H
  H36D 0.5918 0.6390 0.0398 0.085 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
  O1A 0.0929(16) 0.0591(13) 0.0790(15) -0.0161(11) 0.0456(13) -0.0236(11)
  O2A 0.0503(13) 0.0825(14) 0.0676(13) -0.0218(11) 0.0120(10) -0.0399(11)
  N1A 0.0486(14) 0.0368(12) 0.0418(13) -0.0021(10) 0.0050(10) -0.0119(10)
  N2A 0.0470(14) 0.0502(13) 0.0415(13) -0.0138(10) 0.0016(11) -0.0120(11)
  C1A 0.0479(18) 0.0481(17) 0.0529(18) -0.0035(13) 0.0031(14) -0.0186(14)
  C2A 0.0468(18) 0.0409(15) 0.0482(17) -0.0010(13) 0.0000(14) -0.0151(13)
  C11A 0.0426(17) 0.0379(14) 0.0429(16) -0.0057(12) 0.0043(12) -0.0100(12)
  C12A 0.0469(18) 0.0511(16) 0.0589(18) -0.0074(13) -0.0027(14) -0.0228(14)
  N13A 0.0478(15) 0.0590(14) 0.0731(16) 0.0001(12) -0.0031(12) -0.0311(13)
  C14A 0.060(2) 0.0546(17) 0.083(2) 0.0037(15) 0.0000(16) -0.0380(16)
  C15A 0.055(2) 0.0537(17) 0.082(2) -0.0076(15) -0.0029(16) -0.0336(16)
  C16A 0.0451(17) 0.0464(16) 0.0622(18) -0.0081(13) -0.0024(13) -0.0162(14)
  C21A 0.0518(17) 0.0452(15) 0.0454(16) 0.0005(12) 0.0043(13) -0.0187(13)
  C22A 0.092(2) 0.070(2) 0.0583(19) 0.0069(17) -0.0251(17) -0.0278(16)
  C23A 0.133(3) 0.093(3) 0.080(2) 0.000(2) -0.027(2) -0.054(2)
  C24A 0.124(3) 0.065(2) 0.101(3) -0.005(2) -0.011(2) -0.052(2)
  C25A 0.088(2) 0.0482(17) 0.088(2) 0.0047(16) -0.0018(19) -0.0291(17)
  C26A 0.0582(19) 0.0492(16) 0.0611(18) 0.0044(13) -0.0093(14) -0.0240(14)
  C31A 0.0486(17) 0.0457(15) 0.0380(15) -0.0083(12) 0.0036(12) -0.0112(13)
  C32A 0.078(2) 0.0457(16) 0.0497(18) -0.0047(14) 0.0012(15) -0.0107(14)
  C33A 0.098(2) 0.0595(19) 0.0464(18) -0.0140(17) 0.0020(16) -0.0081(15)
  C34A 0.100(3) 0.088(2) 0.0465(18) -0.0224(19) 0.0085(17) -0.0252(18)
  C35A 0.098(3) 0.077(2) 0.070(2) -0.0229(18) 0.0243(19) -0.0439(19)
  C36A 0.073(2) 0.0538(17) 0.061(2) -0.0109(15) 0.0094(16) -0.0236(15)
  O1B 0.0889(15) 0.0491(11) 0.0781(14) 0.0096(10) -0.0469(12) -0.0195(10)
  O2B 0.0470(12) 0.0706(12) 0.0622(12) 0.0155(10) -0.0112(9) -0.0370(10)
  N1B 0.0484(13) 0.0400(12) 0.0419(12) 0.0002(10) -0.0128(10) -0.0179(10)
  N2B 0.0402(13) 0.0503(13) 0.0427(13) 0.0049(10) -0.0076(10) -0.0156(11)
  C1B 0.0466(17) 0.0422(16) 0.0513(17) 0.0018(13) -0.0097(13) -0.0151(13)
  C2B 0.0480(18) 0.0345(14) 0.0449(16) -0.0018(12) -0.0067(14) -0.0154(12)
  C11B 0.0427(17) 0.0393(14) 0.0378(15) -0.0004(12) -0.0075(12) -0.0104(12)
  C12B 0.0485(18) 0.0453(15) 0.0583(17) 0.0008(13) -0.0018(13) -0.0236(14)
  N13B 0.0496(15) 0.0509(13) 0.0662(15) -0.0063(11) -0.0006(12) -0.0256(12)
  C14B 0.066(2) 0.0517(17) 0.067(2) -0.0091(15) -0.0022(15) -0.0317(15)
  C15B 0.053(2) 0.0564(18) 0.075(2) -0.0015(14) 0.0057(15) -0.0356(16)
  C16B 0.0434(17) 0.0461(15) 0.0577(17) -0.0021(13) -0.0049(13) -0.0174(14)
  C21B 0.0589(19) 0.0404(15) 0.0466(16) -0.0010(12) -0.0157(14) -0.0165(13)
  C22B 0.084(2) 0.0621(18) 0.0467(17) -0.0032(16) -0.0033(16) -0.0255(15)
  C23B 0.126(3) 0.082(2) 0.071(2) 0.005(2) -0.015(2) -0.048(2)
  C24B 0.167(4) 0.057(2) 0.087(3) 0.025(2) -0.051(3) -0.045(2)
  C25B 0.126(3) 0.0471(18) 0.084(2) -0.0178(19) -0.036(2) -0.0178(18)
  C26B 0.078(2) 0.0490(16) 0.0603(18) -0.0088(14) -0.0079(15) -0.0226(15)
  C31B 0.0461(16) 0.0418(15) 0.0398(15) -0.0048(12) -0.0035(12) -0.0128(13)
  C32B 0.090(2) 0.0510(17) 0.0533(18) -0.0118(15) -0.0105(16) -0.0156(14)
  C33B 0.128(3) 0.0588(19) 0.0519(19) -0.0116(18) -0.0246(19) -0.0099(16)
  C34B 0.113(3) 0.083(2) 0.0443(18) -0.0168(19) -0.0060(17) -0.0200(18)
  C35B 0.127(3) 0.065(2) 0.0575(19) -0.0051(19) -0.0144(19) -0.0348(17)
  C36B 0.104(2) 0.0552(18) 0.0555(19) 0.0126(16) -0.0162(17) -0.0248(15)
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
  O1A C1A . 1.216(3) yes
  O2A C2A . 1.218(3) yes
  N1A C1A . 1.365(3) yes
  N1A C2A . 1.445(3) yes
  N1A C21A . 1.480(3) yes
  N2A C2A . 1.323(3) yes
  N2A C31A . 1.461(3) yes
  C1A C11A . 1.498(3) yes
  C11A C12A . 1.374(3) no
  C11A C16A . 1.375(3) no
  N13A C12A . 1.338(3) no
  N13A C14A . 1.329(3) no
  C14A C15A . 1.364(3) no
  C15A C16A . 1.371(3) no
  C21A C22A . 1.505(3) no
  C21A C26A . 1.513(3) no
  C22A C23A . 1.529(4) no
  C23A C24A . 1.516(4) no
  C24A C25A . 1.501(4) no
  C25A C26A . 1.515(3) no
  C31A C32A . 1.508(3) no
  C31A C36A . 1.506(3) no
  C32A C33A . 1.521(3) no
  C33A C34A . 1.513(4) no
  C34A C35A . 1.507(4) no
  C35A C36A . 1.517(3) no
  O1B C1B . 1.216(3) yes
  O2B C2B . 1.209(3) yes
  N1B C1B . 1.362(3) yes
  N1B C2B . 1.444(3) yes
  N1B C21B . 1.483(3) yes
  N2B C2B . 1.333(3) yes
  N2B C31B . 1.453(3) yes
  C1B C11B . 1.504(3) yes
  C11B C12B . 1.378(3) no
  C11B C16B . 1.373(3) no
  N13B C12B . 1.334(3) no
  N13B C14B . 1.334(3) no
  C14B C15B . 1.368(3) no
  C15B C16B . 1.370(3) no
  C21B C22B . 1.507(3) no
  C21B C26B . 1.511(3) no
  C22B C23B . 1.519(4) no
  C23B C24B . 1.513(4) no
  C24B C25B . 1.510(4) no
  C25B C26B . 1.523(4) no
  C31B C32B . 1.506(3) no
  C31B C36B . 1.495(3) no
  C32B C33B . 1.519(3) no
  C33B C34B . 1.510(4) no
  C34B C35B . 1.512(4) no
  C35B C36B . 1.520(3) no
_cod_database_code 2008909