#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008284.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_2008284
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  401
_journal_page_last  403
_publ_section_title
;
2-[3-(Pyrrolidin-1-yl)cyclohex-2-en-1-ylidene]propanedinitrile
;
loop_
_publ_author_name
  'S. Selladurai'
  'R. Chandrasekaran'
  'L. Govindasamy'
  'P. Murugan'
  'V. T. Ramakrishnan'
_chemical_formula_sum  'C13 H15 N3'
_chemical_formula_weight  213.28
_chemical_melting_point  225
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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'
_cell_length_a  7.1180(10)
_cell_length_b  20.8940(10)
_cell_length_c  7.768(2)
_cell_angle_alpha  90.0
_cell_angle_beta  92.20(3)
_cell_angle_gamma  90.0
_cell_volume  1154.4(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.227
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0590
_refine_ls_wR_factor_obs  0.1720
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  N1 -0.3552(3) 0.60232(9) 0.6940(3) 0.0717(5) Uani d . 1 . N
  N2 0.1498(3) 0.67533(9) 0.9657(3) 0.0772(6) Uani d . 1 . N
  N3 -0.0324(2) 0.36130(6) 0.6287(2) 0.0436(4) Uani d . 1 . N
  C1 0.0705(2) 0.52269(7) 0.7863(2) 0.0400(4) Uani d . 1 . C
  C2 -0.0220(2) 0.47115(7) 0.7079(2) 0.0401(4) Uani d . 1 . C
  H2 -0.1449(2) 0.47673(7) 0.6657(2) 0.048 Uiso calc R 1 . H
  C3 0.0624(2) 0.41144(7) 0.6901(2) 0.0393(4) Uani d . 1 . C
  C4 0.2653(2) 0.40208(9) 0.7442(3) 0.0516(5) Uani d . 1 . C
  H4A 0.3238(2) 0.37387(9) 0.6628(3) 0.062 Uiso calc R 1 . H
  H4B 0.2729(2) 0.38164(9) 0.8564(3) 0.062 Uiso calc R 1 . H
  C5 0.3720(2) 0.46493(10) 0.7532(3) 0.0548(5) Uani d . 1 . C
  H5A 0.4957(2) 0.45782(10) 0.8064(3) 0.066 Uiso calc R 1 . H
  H5B 0.3883(2) 0.48084(10) 0.6374(3) 0.066 Uiso calc R 1 . H
  C6 0.2687(2) 0.51445(9) 0.8557(2) 0.0476(4) Uani d . 1 . C
  H6A 0.2674(2) 0.50125(9) 0.9753(2) 0.057 Uiso calc R 1 . H
  H6B 0.3343(2) 0.55506(9) 0.8507(2) 0.057 Uiso calc R 1 . H
  C7 -0.0164(2) 0.58220(8) 0.8079(2) 0.0448(4) Uani d . 1 . C
  C8 -0.2044(3) 0.59362(8) 0.7454(2) 0.0506(4) Uani d . 1 . C
  C9 0.0762(3) 0.63358(9) 0.8948(2) 0.0536(5) Uani d . 1 . C
  C10 0.0458(3) 0.29645(9) 0.6092(3) 0.0596(5) Uani d . 1 . C
  H10A 0.0925(3) 0.27971(9) 0.7192(3) 0.072 Uiso calc R 1 . H
  H10B 0.1472(3) 0.29644(9) 0.5292(3) 0.072 Uiso calc R 1 . H
  C11 -0.1179(4) 0.25822(12) 0.5402(6) 0.1111(13) Uani d . 1 . C
  H11A -0.1000(4) 0.24756(12) 0.4204(6) 0.133 Uiso calc R 1 . H
  H11B -0.1269(4) 0.21862(12) 0.6045(6) 0.133 Uiso calc R 1 . H
  C12 -0.2837(4) 0.29351(13) 0.5541(6) 0.1081(12) Uani d . 1 . C
  H12A -0.3559(4) 0.27667(13) 0.6473(6) 0.130 Uiso calc R 1 . H
  H12B -0.3596(4) 0.29003(13) 0.4481(6) 0.130 Uiso calc R 1 . H
  C13 -0.2358(3) 0.36199(9) 0.5883(3) 0.0549(5) Uani d . 1 . C
  H13A -0.2651(3) 0.38819(9) 0.4877(3) 0.066 Uiso calc R 1 . H
  H13B -0.3040(3) 0.37834(9) 0.6846(3) 0.066 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
  N1 0.0586(11) 0.0682(11) 0.0881(14) 0.0094(8) 0.0001(9) 0.0028(9)
  N2 0.0944(15) 0.0570(11) 0.0803(13) -0.0180(10) 0.0034(11) -0.0175(9)
  N3 0.0448(8) 0.0398(7) 0.0459(8) 0.0002(5) -0.0014(5) -0.0021(5)
  C1 0.0423(8) 0.0434(8) 0.0345(8) -0.0045(6) 0.0041(6) 0.0018(6)
  C2 0.0363(7) 0.0433(8) 0.0403(8) -0.0006(6) -0.0022(6) 0.0001(6)
  C3 0.0409(8) 0.0428(8) 0.0341(8) -0.0006(6) 0.0002(6) 0.0014(6)
  C4 0.0434(9) 0.0548(10) 0.0560(10) 0.0073(7) -0.0059(7) -0.0052(8)
  C5 0.0363(8) 0.0681(12) 0.0597(11) -0.0020(7) -0.0015(7) -0.0100(9)
  C6 0.0424(9) 0.0552(10) 0.0448(9) -0.0072(7) -0.0012(7) -0.0053(7)
  C7 0.0508(9) 0.0421(8) 0.0418(9) -0.0049(6) 0.0058(7) -0.0004(6)
  C8 0.0575(11) 0.0416(9) 0.0531(10) 0.0018(7) 0.0075(8) 0.0012(7)
  C9 0.0645(11) 0.0451(9) 0.0516(10) -0.0063(8) 0.0084(8) -0.0020(7)
  C10 0.0717(13) 0.0399(9) 0.0668(12) 0.0071(8) -0.0042(9) -0.0047(8)
  C11 0.097(2) 0.0467(13) 0.187(4) -0.0049(12) -0.032(2) -0.023(2)
  C12 0.074(2) 0.068(2) 0.181(3) -0.0168(13) -0.006(2) -0.049(2)
  C13 0.0453(9) 0.0535(10) 0.0654(12) -0.0066(7) -0.0034(8) -0.0084(8)
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
  N1 C8 . 1.146(3) yes
  N2 C9 . 1.147(3) yes
  N3 C3 . 1.325(2) ?
  N3 C13 . 1.469(2) yes
  N3 C10 . 1.475(2) yes
  C1 C2 . 1.390(2) yes
  C1 C7 . 1.401(2) yes
  C1 C6 . 1.501(2) yes
  C2 C3 . 1.394(2) yes
  C2 H2 . 0.93 ?
  C3 C4 . 1.501(2) yes
  C4 C5 . 1.517(3) yes
  C4 H4A . 0.97 ?
  C4 H4B . 0.97 ?
  C5 C6 . 1.513(2) yes
  C5 H5A . 0.97 ?
  C5 H5B . 0.97 ?
  C6 H6A . 0.97 ?
  C6 H6B . 0.97 ?
  C7 C9 . 1.417(2) yes
  C7 C8 . 1.426(3) yes
  C10 C11 . 1.495(3) yes
  C10 H10A . 0.97 ?
  C10 H10B . 0.97 ?
  C11 C12 . 1.399(4) yes
  C11 H11A . 0.97 ?
  C11 H11B . 0.97 ?
  C12 C13 . 1.493(3) yes
  C12 H12A . 0.97 ?
  C12 H12B . 0.97 ?
  C13 H13A . 0.97 ?
  C13 H13B . 0.97 ?