data_2013227
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o60
_journal_page_last  o61
_publ_section_title
;
Conformation of N-methyl-4-piperidyl 2,4-dinitrobenzoate
;
loop_
_publ_author_name
  'Andrau, Laura'
  'White, Jonathan'
_chemical_formula_moiety  'C13 H15 N3 O6'
_chemical_formula_sum  'C13 H15 N3 O6'
_chemical_formula_weight  309.28
_chemical_melting_point  .341E-305
_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  6.040(3)
_cell_length_b  13.303(5)
_cell_length_c  17.699(7)
_cell_angle_alpha  90
_cell_angle_beta  94.096(8)
_cell_angle_gamma  90
_cell_volume  1418.4(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  130(2)
_exptl_crystal_density_diffrn  1.448
_diffrn_ambient_temperature  130.0(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 0.5166(4) 0.58042(16) 0.37429(14) 0.0246(6) Uani d . 1 . . C
  C2 0.7151(4) 0.59858(18) 0.42946(16) 0.0288(6) Uani d . 1 . . C
  C3 0.7719(4) 0.71038(18) 0.42932(16) 0.0281(6) Uani d . 1 . . C
  C4 0.3909(4) 0.75462(18) 0.39534(15) 0.0266(6) Uani d . 1 . . C
  C5 0.3232(4) 0.64419(18) 0.39445(15) 0.0257(6) Uani d . 1 . . C
  C6 0.6440(5) 0.87898(19) 0.44762(17) 0.0328(6) Uani d . 1 . . C
  C7 0.5287(4) 0.41043(17) 0.33026(13) 0.0259(6) Uani d . 1 . . C
  C8 0.4029(4) 0.31227(17) 0.33187(13) 0.0241(5) Uani d . 1 . . C
  C9 0.4847(4) 0.22388(17) 0.36624(13) 0.0238(5) Uani d . 1 . . C
  C10 0.3691(4) 0.13469(18) 0.36076(13) 0.0251(6) Uani d . 1 . . C
  C11 0.1634(4) 0.13496(16) 0.32174(12) 0.0234(5) Uani d . 1 . . C
  C12 0.0744(4) 0.22087(18) 0.28761(13) 0.0267(6) Uani d . 1 . . C
  C13 0.1948(4) 0.30890(18) 0.29322(14) 0.0274(6) Uani d . 1 . . C
  N1 0.5832(3) 0.77231(14) 0.44892(11) 0.0253(5) Uani d . 1 . . N
  N2 0.6986(3) 0.22487(16) 0.41149(11) 0.0290(5) Uani d . 1 . . N
  N3 0.0317(3) 0.04132(15) 0.31820(11) 0.0291(5) Uani d . 1 . . N
  O1 0.4419(2) 0.47566(11) 0.37704(9) 0.0272(4) Uani d . 1 . . O
  O2 0.6703(3) 0.42739(12) 0.28798(9) 0.0351(5) Uani d . 1 . . O
  O3 0.7879(3) 0.30659(13) 0.42425(10) 0.0367(5) Uani d . 1 . . O
  O4 0.7777(3) 0.14396(13) 0.43376(9) 0.0366(5) Uani d . 1 . . O
  O5 0.1025(3) -0.03040(12) 0.35554(10) 0.0362(5) Uani d . 1 . . O
  O6 -0.1423(3) 0.04116(13) 0.27776(10) 0.0391(5) Uani d . 1 . . O
  H1 0.558(4) 0.5948(17) 0.3217(13) 0.028(6) Uiso d . 1 . . H
  H2A 0.842(4) 0.5577(17) 0.4169(12) 0.024(6) Uiso d . 1 . . H
  H2B 0.682(4) 0.5762(19) 0.4790(16) 0.041(8) Uiso d . 1 . . H
  H3A 0.889(4) 0.7261(16) 0.4664(13) 0.025(6) Uiso d . 1 . . H
  H3B 0.818(4) 0.7298(19) 0.3766(16) 0.045(8) Uiso d . 1 . . H
  H4A 0.420(4) 0.7760(18) 0.3414(16) 0.039(7) Uiso d . 1 . . H
  H4B 0.269(4) 0.7947(17) 0.4102(13) 0.026(6) Uiso d . 1 . . H
  H5A 0.286(3) 0.6235(15) 0.4466(12) 0.017(6) Uiso d . 1 . . H
  H5B 0.196(4) 0.6338(16) 0.3589(13) 0.024(6) Uiso d . 1 . . H
  H6A 0.678(4) 0.8990(18) 0.3949(15) 0.039(7) Uiso d . 1 . . H
  H6B 0.771(4) 0.8896(18) 0.4832(14) 0.035(7) Uiso d . 1 . . H
  H6C 0.516(4) 0.9206(19) 0.4643(14) 0.042(7) Uiso d . 1 . . H
  H10 0.423(3) 0.0770(17) 0.3838(12) 0.019(6) Uiso d . 1 . . H
  H12 -0.069(4) 0.2177(18) 0.2611(14) 0.038(7) Uiso d . 1 . . H
  H13 0.135(4) 0.3702(17) 0.2696(12) 0.024(6) Uiso d . 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
  C1 0.0265(13) 0.0169(12) 0.0307(15) -0.0050(10) 0.0032(11) -0.0006(10)
  C2 0.0235(13) 0.0218(14) 0.0407(17) 0.0035(11) -0.0008(12) 0.0010(12)
  C3 0.0201(13) 0.0279(14) 0.0355(16) -0.0019(10) -0.0041(12) -0.0038(12)
  C4 0.0230(13) 0.0239(14) 0.0324(15) 0.0032(11) -0.0011(11) -0.0003(12)
  C5 0.0199(13) 0.0282(14) 0.0285(14) -0.0013(10) -0.0026(11) -0.0023(11)
  C6 0.0356(16) 0.0254(14) 0.0374(17) -0.0058(12) 0.0033(14) -0.0028(13)
  C7 0.0250(13) 0.0255(14) 0.0268(14) 0.0016(10) -0.0006(11) -0.0030(11)
  C8 0.0270(13) 0.0227(13) 0.0231(13) 0.0000(10) 0.0038(10) -0.0024(10)
  C9 0.0223(12) 0.0264(13) 0.0226(12) 0.0038(10) 0.0004(10) -0.0045(10)
  C10 0.0299(14) 0.0212(14) 0.0243(13) 0.0050(10) 0.0032(11) 0.0007(11)
  C11 0.0268(13) 0.0211(13) 0.0225(13) 0.0000(10) 0.0020(10) -0.0041(10)
  C12 0.0254(13) 0.0293(14) 0.0245(13) -0.0014(11) -0.0036(11) -0.0017(11)
  C13 0.0289(14) 0.0203(13) 0.0325(14) 0.0029(11) -0.0023(11) 0.0026(11)
  N1 0.0239(10) 0.0200(11) 0.0315(12) -0.0025(8) -0.0012(9) -0.0019(9)
  N2 0.0245(11) 0.0342(13) 0.0283(12) 0.0025(10) 0.0005(9) -0.0030(10)
  N3 0.0341(12) 0.0236(12) 0.0296(12) -0.0024(9) 0.0026(10) -0.0040(9)
  O1 0.0293(9) 0.0206(9) 0.0322(10) -0.0033(7) 0.0049(7) -0.0034(7)
  O2 0.0377(10) 0.0305(10) 0.0388(11) -0.0033(8) 0.0143(9) -0.0037(8)
  O3 0.0314(10) 0.0386(11) 0.0391(11) -0.0082(8) -0.0044(8) -0.0042(8)
  O4 0.0315(10) 0.0387(11) 0.0389(11) 0.0115(8) -0.0035(8) 0.0037(9)
  O5 0.0388(10) 0.0223(10) 0.0474(11) 0.0019(8) 0.0031(9) 0.0070(8)
  O6 0.0382(11) 0.0341(11) 0.0432(11) -0.0103(8) -0.0103(9) -0.0029(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
  C1 O1 . 1.467(3) y
  C1 C5 . 1.507(3) y
  C1 C2 . 1.511(3) y
  C1 H1 . 1.00(2) ?
  C2 C3 . 1.526(3) y
  C2 H2A . 0.98(2) ?
  C2 H2B . 0.96(3) ?
  C3 N1 . 1.468(3) y
  C3 H3A . 0.95(2) ?
  C3 H3B . 1.03(3) ?
  C4 N1 . 1.465(3) y
  C4 C5 . 1.525(3) y
  C4 H4A . 1.02(3) ?
  C4 H4B . 0.96(2) ?
  C5 H5A . 1.01(2) ?
  C5 H5B . 0.96(2) ?
  C6 N1 . 1.466(3) y
  C6 H6A . 1.01(3) ?
  C6 H6B . 0.97(3) ?
  C6 H6C . 1.01(3) ?
  C7 O2 . 1.197(3) ?
  C7 O1 . 1.333(3) ?
  C7 C8 . 1.512(3) ?
  C8 C13 . 1.389(3) ?
  C8 C9 . 1.398(3) ?
  C9 C10 . 1.376(3) ?
  C9 N2 . 1.471(3) ?
  C10 C11 . 1.378(3) ?
  C10 H10 . 0.92(2) ?
  C11 C12 . 1.383(3) ?
  C11 N3 . 1.477(3) ?
  C12 C13 . 1.378(3) ?
  C12 H12 . 0.96(2) ?
  C13 H13 . 0.97(2) ?
  N2 O3 . 1.227(2) ?
  N2 O4 . 1.231(2) ?
  N3 O5 . 1.221(2) ?
  N3 O6 . 1.228(2) ?