data_2012825
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o433
_journal_page_last  o435
_publ_section_title
;
2-(exo-Tricyclo[5.2.1.0^2,6^]deca-4,8-dien-3-endo-yl)acetaldehyde
2,4-dinitrophenylhydrazone
;
loop_
_publ_author_name
  'Abdul Ajees, A.'
  'Palani, N.'
  'Balasubramanian, K. K.'
_chemical_name_common
;
exo-Tricyclo[5.2.1.0^2,6^]deca-4,8-dienyl-3-endoacetaldehyde
2,4-dinitrophenylhydrazone
;
_chemical_formula_moiety  'C18 H18 N4 O4'
_chemical_formula_sum  'C18 H18 N4 O4'
_chemical_formula_weight  354.36
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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  6.4120(10)
_cell_length_b  14.569(2)
_cell_length_c  19.144(3)
_cell_angle_alpha  90
_cell_angle_beta  105.020(10)
_cell_angle_gamma  90
_cell_volume  1727.4(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.363
_diffrn_ambient_temperature  293(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
  C1 0.6104(6) 0.4045(2) 0.80733(19) 0.0669(9) Uani d . 1 . . C
  H1 0.4929 0.3768 0.7701 0.080 Uiso calc R 1 . . H
  C2 0.6054(5) 0.5101(2) 0.81235(15) 0.0521(8) Uani d . 1 . . C
  H2 0.6644 0.5378 0.7749 0.063 Uiso calc R 1 . . H
  C3 0.3893(6) 0.5550(2) 0.81260(16) 0.0593(8) Uani d . 1 . . C
  H3 0.2764 0.5079 0.8032 0.071 Uiso calc R 1 . . H
  C4 0.4250(7) 0.5889(3) 0.88937(19) 0.0729(10) Uani d . 1 . . C
  H4 0.3175 0.6168 0.9065 0.087 Uiso calc R 1 . . H
  C5 0.6173(8) 0.5757(3) 0.92880(19) 0.0753(11) Uani d . 1 . . C
  H5 0.6630 0.5941 0.9769 0.090 Uiso calc R 1 . . H
  C6 0.7626(6) 0.5273(2) 0.88977(18) 0.0619(9) Uani d . 1 . . C
  H6 0.8880 0.5646 0.8876 0.074 Uiso calc R 1 . . H
  C7 0.8262(6) 0.4296(2) 0.91670(18) 0.0620(9) Uani d . 1 . . C
  H7 0.8880 0.4228 0.9689 0.074 Uiso calc R 1 . . H
  C8 0.9605(7) 0.3925(3) 0.8689(2) 0.0775(11) Uani d . 1 . . C
  H8 1.1084 0.3815 0.8830 0.093 Uiso calc R 1 . . H
  C9 0.8331(7) 0.3787(3) 0.8044(2) 0.0728(10) Uani d . 1 . . C
  H9 0.8737 0.3568 0.7642 0.087 Uiso calc R 1 . . H
  C10 0.6200(6) 0.3770(2) 0.8851(2) 0.0689(10) Uani d . 1 . . C
  H10A 0.4984 0.3999 0.9014 0.083 Uiso calc R 1 . . H
  H10B 0.6360 0.3114 0.8932 0.083 Uiso calc R 1 . . H
  C11 0.3191(6) 0.6332(3) 0.75893(17) 0.0676(10) Uani d . 1 . . C
  H11A 0.1902 0.6612 0.7671 0.081 Uiso calc R 1 . . H
  H11B 0.4317 0.6795 0.7683 0.081 Uiso calc R 1 . . H
  C12 0.2736(6) 0.6049(2) 0.68187(16) 0.0600(8) Uani d . 1 . . C
  H12 0.1549 0.5680 0.6617 0.072 Uiso calc R 1 . . H
  N13 0.3959(4) 0.63098(18) 0.64402(13) 0.0557(7) Uani d . 1 . . N
  N14 0.3403(4) 0.60320(17) 0.57229(13) 0.0533(6) Uani d . 1 . . N
  H14 0.2264 0.5707 0.5554 0.064 Uiso calc R 1 . . H
  C15 0.4681(5) 0.62800(19) 0.52941(16) 0.0489(7) Uani d . 1 . . C
  C16 0.4255(5) 0.60559(19) 0.45516(15) 0.0463(7) Uani d . 1 . . C
  C17 0.5593(5) 0.6339(2) 0.41305(18) 0.0542(8) Uani d . 1 . . C
  H17 0.5265 0.6195 0.3641 0.065 Uiso calc R 1 . . H
  C18 0.7404(5) 0.6834(2) 0.44444(19) 0.0569(8) Uani d . 1 . . C
  C19 0.7918(5) 0.7056(2) 0.5171(2) 0.0622(9) Uani d . 1 . . C
  H19 0.9163 0.7390 0.5375 0.075 Uiso calc R 1 . . H
  C20 0.6591(5) 0.6784(2) 0.55892(18) 0.0573(8) Uani d . 1 . . C
  H20 0.6955 0.6934 0.6078 0.069 Uiso calc R 1 . . H
  N21 0.2393(4) 0.55250(18) 0.41859(13) 0.0521(6) Uani d . 1 . . N
  O22 0.1074(4) 0.52992(16) 0.45252(11) 0.0609(6) Uani d . 1 . . O
  O23 0.2178(4) 0.52949(19) 0.35571(12) 0.0768(8) Uani d . 1 . . O
  N24 0.8798(5) 0.7136(2) 0.3998(2) 0.0744(9) Uani d . 1 . . N
  O25 0.8277(5) 0.6973(3) 0.33548(19) 0.1089(11) Uani d . 1 . . O
  O26 1.0456(5) 0.75424(19) 0.42982(18) 0.0915(9) Uani d . 1 . . O
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
  C1 0.073(2) 0.060(2) 0.064(2) -0.0031(17) 0.0114(17) -0.0136(16)
  C2 0.066(2) 0.0511(17) 0.0388(14) 0.0007(14) 0.0125(13) 0.0024(12)
  C3 0.063(2) 0.0632(19) 0.0512(17) 0.0058(16) 0.0139(15) -0.0014(15)
  C4 0.084(3) 0.081(3) 0.060(2) 0.013(2) 0.030(2) -0.0063(18)
  C5 0.113(3) 0.061(2) 0.0479(18) 0.002(2) 0.013(2) -0.0080(15)
  C6 0.065(2) 0.0561(19) 0.0575(18) -0.0121(16) 0.0042(15) 0.0021(15)
  C7 0.061(2) 0.067(2) 0.0526(17) -0.0045(17) 0.0065(15) 0.0127(15)
  C8 0.070(2) 0.076(2) 0.088(3) 0.015(2) 0.023(2) 0.027(2)
  C9 0.082(3) 0.065(2) 0.077(2) 0.0220(19) 0.030(2) 0.0078(18)
  C10 0.073(2) 0.0535(19) 0.085(2) -0.0070(17) 0.0287(19) 0.0051(18)
  C11 0.082(3) 0.065(2) 0.0563(19) 0.0165(18) 0.0192(17) 0.0021(16)
  C12 0.063(2) 0.061(2) 0.0514(17) 0.0072(16) 0.0075(15) 0.0077(15)
  N13 0.0627(17) 0.0537(15) 0.0486(14) 0.0048(12) 0.0108(12) -0.0004(11)
  N14 0.0559(16) 0.0541(15) 0.0485(13) 0.0003(12) 0.0111(11) -0.0005(11)
  C15 0.0494(17) 0.0391(15) 0.0570(17) 0.0062(12) 0.0120(13) 0.0039(12)
  C16 0.0442(16) 0.0408(15) 0.0531(16) 0.0007(12) 0.0110(13) 0.0020(12)
  C17 0.0498(18) 0.0493(16) 0.0653(19) 0.0040(14) 0.0184(15) 0.0037(14)
  C18 0.0505(19) 0.0454(16) 0.080(2) 0.0013(13) 0.0265(16) 0.0033(15)
  C19 0.0499(19) 0.0461(17) 0.089(2) -0.0030(14) 0.0158(17) -0.0051(16)
  C20 0.0563(19) 0.0469(16) 0.0648(19) 0.0013(14) 0.0086(15) -0.0061(14)
  N21 0.0500(15) 0.0536(15) 0.0516(14) -0.0024(11) 0.0110(11) 0.0038(11)
  O22 0.0562(13) 0.0673(14) 0.0612(13) -0.0153(11) 0.0188(10) 0.0003(10)
  O23 0.0778(17) 0.101(2) 0.0517(13) -0.0260(15) 0.0172(11) -0.0112(13)
  N24 0.0575(19) 0.0648(18) 0.109(3) -0.0027(15) 0.0356(18) 0.0114(18)
  O25 0.094(2) 0.147(3) 0.099(2) -0.031(2) 0.0501(19) 0.004(2)
  O26 0.0628(17) 0.0729(17) 0.144(3) -0.0125(14) 0.0364(17) 0.0116(17)
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
  C1 C9 . 1.492(5) ?
  C1 C10 . 1.527(5) ?
  C1 C2 . 1.542(5) ?
  C1 H1 . 0.9800 ?
  C2 C3 . 1.534(4) ?
  C2 C6 . 1.582(4) ?
  C2 H2 . 0.9800 ?
  C3 C4 . 1.511(4) ?
  C3 C11 . 1.522(4) ?
  C3 H3 . 0.9800 ?
  C4 C5 . 1.283(5) ?
  C4 H4 . 0.9300 ?
  C5 C6 . 1.511(5) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.533(5) ?
  C6 H6 . 0.9800 ?
  C7 C8 . 1.509(5) ?
  C7 C10 . 1.512(5) ?
  C7 H7 . 0.9800 ?
  C8 C9 . 1.309(5) ?
  C8 H8 . 0.9300 ?
  C9 H9 . 0.9300 ?
  C10 H10A . 0.9700 ?
  C10 H10B . 0.9700 ?
  C11 C12 . 1.486(4) ?
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?
  C12 N13 . 1.256(4) ?
  C12 H12 . 0.9300 ?
  N13 N14 . 1.387(3) ?
  N14 C15 . 1.351(4) ?
  N14 H14 . 0.8600 ?
  C15 C16 . 1.414(4) ?
  C15 C20 . 1.415(4) ?
  C16 C17 . 1.384(4) ?
  C16 N21 . 1.442(4) ?
  C17 C18 . 1.367(5) ?
  C17 H17 . 0.9300 ?
  C18 C19 . 1.382(5) ?
  C18 N24 . 1.456(4) ?
  C19 C20 . 1.369(5) ?
  C19 H19 . 0.9300 ?
  C20 H20 . 0.9300 ?
  N21 O23 . 1.222(3) ?
  N21 O22 . 1.237(3) ?
  N24 O25 . 1.212(4) ?
  N24 O26 . 1.223(4) ?