data_8101128 _journal_name_full 'Zeitschrift fur Kristallographie - NCS' _journal_year 2001 loop_ _publ_author_name 'Fukui, Keijiro' 'Hesek, Dusan' 'Oelgem\"oller, Michael' 'Inoue, Yoshihisa' _publ_section_title ; Crystal structure of N-Cyclooctylidene-N'-(2,4-dinitrophenyl)-hydrazine, C14H18N4O4 ; _chemical_formula_weight 306.32 _chemical_formula_sum 'C14 H18 N4 O4 ' _chemical_formula_moiety 'C14 H18 N4 O4 ' _cell_length_a 9.23(2) _cell_length_b 7.31(2) _cell_length_c 21.64(2) _cell_angle_alpha 90 _cell_angle_beta 90.5(1) _cell_angle_gamma 90 _cell_volume 1459(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296.2 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' _exptl_crystal_density_diffrn 1.394 _diffrn_ambient_temperature 296.2 _refine_ls_R_factor_obs 0.0492 _refine_ls_wR_factor_obs 0.0359 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_calc_attached_atom _atom_site_occupancy _atom_site_refinement_flags O15 0.6213(2) 0.3614(2) -0.0161(1) 0.0614(2) Uani d . 1.00 . O16 0.7782(2) 0.3590(2) -0.0885(1) 0.0700(3) Uani d . 1.00 . O17 1.0445(2) -0.1660(2) -0.1420(1) 0.0876(3) Uani d . 1.00 . O18 1.0841(3) -0.3725(2) -0.0733(1) 0.0589(4) Uani d . 1.00 . N1 0.5624(2) -0.0056(2) 0.1141(1) 0.0406(3) Uani d . 1.00 . N2 0.6082(2) 0.0875(2) 0.0620(1) 0.0405(3) Uani d . 1.00 . N3 0.7168(2) 0.2841(1) -0.0456(1) 0.0438(2) Uani d . 1.00 . N4 1.0188(2) -0.2375(2) -0.0923(1) 0.0447(2) Uani d . 1.00 . C1 0.4726(2) 0.0803(2) 0.1486(1) 0.0380(3) Uani d . 1.00 . C2 0.4167(2) 0.2710(2) 0.1367(1) 0.0418(3) Uani d . 1.00 . C3 0.5216(2) 0.4249(2) 0.1556(1) 0.0468(3) Uani d . 1.00 . C4 0.5508(2) 0.4429(2) 0.2252(1) 0.0493(3) Uani d . 1.00 . C5 0.6345(2) 0.2823(2) 0.2540(2) 0.0508(4) Uani d . 1.00 . C6 0.5461(1) 0.1479(1) 0.2921(1) 0.0595(2) Uani d . 1.00 . C7 0.4042(2) 0.0808(1) 0.2638(1) 0.0557(3) Uani d . 1.00 . C8 0.4177(1) -0.0257(1) 0.2031(1) 0.0527(2) Uani d . 1.00 . C9 0.7051(2) 0.0093(2) 0.0240(1) 0.0340(4) Uani d . 1.00 . C10 0.7599(2) -0.1698(2) 0.0363(1) 0.0404(4) Uani d . 1.00 . C11 0.8609(2) -0.2489(2) -0.0009(1) 0.0393(4) Uani d . 1.00 . C12 0.9101(2) -0.1548(2) -0.0530(1) 0.0356(4) Uani d . 1.00 . C13 0.8604(3) 0.0169(2) -0.0673(2) 0.0356(5) Uani d . 1.00 . C14 0.7593(3) 0.0993(3) -0.0291(2) 0.0348(5) Uani d . 1.00 . H1 0.715(3) 0.332(3) 0.2807(16) 0.060(5) Uiso d . 1.00 . H2 0.724(2) -0.242(2) 0.0723(15) 0.053(5) Uiso d . 1.00 . H3 0.898(2) -0.367(2) 0.0087(15) 0.061(4) Uiso d . 1.00 . H4 0.888(2) 0.085(2) -0.1014(13) 0.047(4) Uiso d . 1.00 . H5 0.582(2) 0.203(3) 0.0543(15) 0.051(5) Uiso d . 1.00 . H6 0.609(2) 0.551(2) 0.2305(14) 0.063(5) Uiso d . 1.00 . H7 0.326(2) 0.284(2) 0.1584(14) 0.049(4) Uiso d . 1.00 . H8 0.475(2) 0.537(2) 0.1417(14) 0.059(4) Uiso d . 1.00 . H9 0.685(2) 0.208(2) 0.2217(17) 0.057(4) Uiso d . 1.00 . H10 0.337(3) 0.190(2) 0.2593(17) 0.052(4) Uiso d . 1.00 . H11 0.317(3) -0.056(2) 0.1928(16) 0.066(4) Uiso d . 1.00 . H12 0.457(3) 0.460(3) 0.2481(17) 0.052(6) Uiso d . 1.00 . H13 0.600(3) 0.033(3) 0.3047(17) 0.075(6) Uiso d . 1.00 . H14 0.478(3) -0.133(3) 0.2095(17) 0.067(6) Uiso d . 1.00 . H15 0.618(3) 0.407(3) 0.1347(17) 0.053(6) Uiso d . 1.00 . H16 0.525(2) 0.195(2) 0.3352(14) 0.091(5) Uiso d . 1.00 . H17 0.351(2) -0.002(2) 0.2941(14) 0.072(2) Uiso d . 1.00 . H18 0.390(3) 0.283(2) 0.0921(16) 0.062(5) Uiso d . 1.00 . 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 O15 0.0716(6) 0.0523(5) 0.0588(5) 0.0285(4) 0.0189(4) 0.0133(4) O16 0.0827(7) 0.0568(6) 0.0681(5) 0.0237(5) 0.0299(5) 0.0305(5) O17 0.1150(9) 0.0861(7) 0.0488(7) 0.0438(6) 0.0366(6) 0.0179(6) O18 0.0668(11) 0.0504(7) 0.0584(8) 0.0231(6) 0.0123(7) 0.0021(6) N1 0.0472(9) 0.0373(7) 0.0365(8) -0.0021(6) 0.0077(7) 0.0007(6) N2 0.0477(7) 0.0371(7) 0.0356(7) 0.0050(6) 0.0073(5) 0.0027(5) N3 0.0483(6) 0.0430(5) 0.0398(5) 0.0106(4) 0.0021(4) 0.0067(4) N4 0.0508(6) 0.0450(5) 0.0371(6) 0.0073(4) 0.0046(4) -0.0042(4) C1 0.0376(7) 0.0390(6) 0.0374(7) -0.0037(5) 0.0027(5) -0.0053(5) C2 0.0368(8) 0.0468(8) 0.0411(6) 0.0068(6) -0.0017(6) -0.0047(6) C3 0.0544(8) 0.0356(8) 0.0485(7) 0.0045(6) -0.0058(6) 0.0005(6) C4 0.0528(7) 0.0412(8) 0.0528(6) -0.0007(6) -0.0075(5) -0.0099(6) C5 0.0454(8) 0.0591(8) 0.0467(10) 0.0016(7) -0.0074(8) -0.0016(6) C6 0.0695(6) 0.0656(5) 0.0388(5) 0.0049(4) 0.0063(4) 0.0030(4) C7 0.0596(6) 0.0586(6) 0.0480(5) -0.0020(4) 0.0247(4) 0.0001(5) C8 0.0614(4) 0.0457(5) 0.0497(5) -0.0093(4) 0.0194(4) -0.0019(3) C9 0.0348(6) 0.0364(10) 0.0305(7) -0.0002(7) -0.0012(5) -0.0017(6) C10 0.0479(6) 0.0347(5) 0.0375(5) 0.0012(4) 0.0051(4) 0.0043(3) C11 0.0441(7) 0.0332(7) 0.0399(7) 0.0038(6) 0.0014(6) 0.0009(6) C12 0.0369(11) 0.0379(7) 0.0315(8) 0.0031(6) -0.0013(7) -0.0044(5) C13 0.0380(7) 0.0393(7) 0.0283(7) 0.0011(6) -0.0019(5) 0.0016(5) C14 0.0364(8) 0.0346(8) 0.0333(6) 0.0031(6) -0.0034(6) 0.0017(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 N1 1.226(2) 1_555 1_555 yes O2 N1 1.217(2) 1_555 1_555 yes O3 N2 1.224(2) 1_555 1_555 yes O4 N2 1.235(3) 1_555 1_555 yes N1 C3 1.461(3) 1_555 1_555 yes N2 C5 1.454(3) 1_555 1_555 yes N3 N4 1.394(2) 1_555 1_555 yes N3 C6 1.354(3) 1_555 1_555 yes N4 C7 1.286(3) 1_555 1_555 yes C1 C2 1.368(3) 1_555 1_555 yes C1 C6 1.417(3) 1_555 1_555 yes C2 C3 1.394(3) 1_555 1_555 yes C3 C4 1.366(3) 1_555 1_555 yes C4 C5 1.384(3) 1_555 1_555 yes C5 C6 1.414(3) 1_555 1_555 yes C7 C8 1.505(3) 1_555 1_555 yes C7 C15 1.497(3) 1_555 1_555 yes C8 C10 1.541(3) 1_555 1_555 yes C9 C10 1.526(4) 1_555 1_555 yes C9 C12 1.524(4) 1_555 1_555 yes C12 C13 1.531(3) 1_555 1_555 yes C13 C14 1.534(3) 1_555 1_555 yes C14 C15 1.530(4) 1_555 1_555 yes