#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008312.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_2008312
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  681
_journal_page_last  683
_publ_section_title
;
Nitrate salt of protonated 2-(diethylaminomethyl)phenol
;
loop_
_publ_author_name
  "Bouayad, Abdelouahed"
  "Dartiguenave, Mich\`ele"
  "Lamand\'e, Lydia"
  "El Ghadraoui, El Houssine"
  "Beauchamp, Andr\'e L."
_chemical_name_common
;
2-(Diethylaminomethyl)phenol Nitrate
;
_chemical_formula_moiety  'C11 H18 N2 O4'
_chemical_formula_sum  'C11 H18 N O + , N O3 -'
_chemical_formula_structural  '(C11 H18 N O) N O3'
_chemical_formula_weight  242.274
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, z'
  'x, -y+1/2, z+1/2'
  '-x+1/2, -y, z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, -z'
  '-x, y-1/2, -z-1/2'
  'x-1/2, y, -z-1/2'
_cell_length_a  10.0090(13)
_cell_length_b  15.472(2)
_cell_length_c  16.216(2)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2511.3(5)
_cell_formula_units_Z  8
_cell_measurement_temperature  160(3)
_exptl_crystal_density_diffrn  1.282
_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_group
_atom_site_type_symbol
  O1 0.21686(15) 0.31424(9) 0.37296(10) 0.0380(4) Uani d . 1 . O
  H1 0.287(3) 0.2900(16) 0.4015(16) 0.055(8) Uiso d . 1 . H
  O10 0.40532(17) 0.23710(10) 0.46247(10) 0.0472(4) Uani d . 1 . O
  O11 0.58111(15) 0.15738(10) 0.45795(11) 0.0518(5) Uani d . 1 . O
  O12 0.52733(16) 0.23555(12) 0.35186(10) 0.0522(5) Uani d . 1 . O
  N1 0.50669(18) 0.21023(11) 0.42319(11) 0.0348(4) Uani d . 1 . N
  N7 -0.07463(16) 0.37054(10) 0.38229(10) 0.0251(4) Uani d . 1 . N
  H7 -0.0188(19) 0.3464(11) 0.4183(12) 0.018(5) Uiso d . 1 . H
  C1 0.2346(2) 0.40096(12) 0.36793(12) 0.0307(5) Uani d . 1 . C
  C2 0.1288(2) 0.44883(12) 0.33392(12) 0.0289(5) Uani d . 1 . C
  C3 0.1437(2) 0.53704(13) 0.32429(14) 0.0357(5) Uani d . 1 . C
  H3 0.066(2) 0.5694(15) 0.3026(15) 0.051(7) Uiso d . 1 . H
  C4 0.2609(2) 0.57866(14) 0.34724(15) 0.0406(6) Uani d . 1 . C
  H4 0.269(2) 0.6372(16) 0.3390(15) 0.049(7) Uiso d . 1 . H
  C5 0.3633(2) 0.53077(14) 0.38152(16) 0.0411(6) Uani d . 1 . C
  H5 0.444(3) 0.5563(15) 0.3965(15) 0.047(7) Uiso d . 1 . H
  C6 0.3516(2) 0.44229(14) 0.39225(15) 0.0367(5) Uani d . 1 . C
  H6 0.423(2) 0.4097(14) 0.4148(14) 0.039(6) Uiso d . 1 . H
  C7 0.0048(2) 0.40212(14) 0.30844(13) 0.0322(5) Uani d . 1 . C
  H7A 0.026(2) 0.3518(15) 0.2752(14) 0.042(6) Uiso d . 1 . H
  H7B -0.055(2) 0.4391(13) 0.2754(14) 0.037(6) Uiso d . 1 . H
  C10 -0.1369(2) 0.44391(13) 0.43017(13) 0.0293(5) Uani d . 1 . C
  H10A -0.168(2) 0.4218(14) 0.4840(16) 0.043(6) Uiso d . 1 . H
  H10B -0.067(2) 0.4854(13) 0.4393(13) 0.034(6) Uiso d . 1 . H
  C11 -0.2530(3) 0.48586(18) 0.38728(19) 0.0497(6) Uani d . 1 . C
  H11A -0.276(2) 0.5388(17) 0.4181(15) 0.051(7) Uiso d . 1 . H
  H11B -0.331(3) 0.4411(18) 0.3796(18) 0.072(9) Uiso d . 1 . H
  H11C -0.223(3) 0.5085(17) 0.3334(19) 0.068(9) Uiso d . 1 . H
  C12 -0.1755(2) 0.30302(14) 0.35804(16) 0.0349(5) Uani d . 1 . C
  H12A -0.221(2) 0.3263(14) 0.3110(15) 0.043(6) Uiso d . 1 . H
  H12B -0.238(2) 0.2973(13) 0.4031(14) 0.039(6) Uiso d . 1 . H
  C13 -0.1112(3) 0.21656(16) 0.34073(19) 0.0502(7) Uani d . 1 . C
  H13A -0.041(3) 0.2195(17) 0.296(2) 0.076(9) Uiso d . 1 . H
  H13B -0.184(3) 0.1815(19) 0.3216(19) 0.076(9) Uiso d . 1 . H
  H13C -0.057(3) 0.1959(17) 0.388(2) 0.065(8) 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
  O1 0.0413(9) 0.0221(8) 0.0506(11) -0.0019(6) 0.0011(8) 0.0017(6)
  O10 0.0598(10) 0.0441(9) 0.0377(9) 0.0115(8) 0.0127(8) 0.0056(7)
  O11 0.0388(9) 0.0574(10) 0.0591(11) 0.0054(8) -0.0056(8) 0.0194(9)
  O12 0.0505(10) 0.0750(12) 0.0311(10) -0.0104(9) 0.0035(8) 0.0173(8)
  N1 0.0372(10) 0.0358(10) 0.0313(11) -0.0108(9) -0.0044(9) 0.0051(8)
  N7 0.0291(8) 0.0248(9) 0.0215(9) 0.0006(7) -0.0039(8) 0.0021(7)
  C1 0.0353(11) 0.0282(10) 0.0286(12) -0.0018(9) 0.0117(9) -0.0009(9)
  C2 0.0380(11) 0.0275(10) 0.0214(11) -0.0038(9) 0.0087(9) -0.0026(8)
  C3 0.0469(13) 0.0319(12) 0.0283(12) 0.0014(11) 0.0124(11) 0.0028(9)
  C4 0.0555(15) 0.0238(11) 0.0426(14) -0.0085(11) 0.0171(12) -0.0028(9)
  C5 0.0392(12) 0.0363(13) 0.0478(15) -0.0106(11) 0.0148(12) -0.0090(10)
  C6 0.0321(12) 0.0369(13) 0.0410(14) -0.0022(10) 0.0103(10) -0.0030(10)
  C7 0.0422(13) 0.0349(12) 0.0194(11) 0.0009(10) 0.0024(9) 0.0017(9)
  C10 0.0291(11) 0.0311(11) 0.0276(12) 0.0003(9) -0.0013(9) -0.0001(9)
  C11 0.0483(14) 0.0482(15) 0.0527(17) 0.0189(13) -0.0105(14) 0.0002(13)
  C12 0.0383(12) 0.0332(12) 0.0331(13) -0.0086(10) -0.0085(11) 0.0016(9)
  C13 0.0718(19) 0.0320(13) 0.0468(17) -0.0115(13) 0.0091(15) -0.0104(11)
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
  O1 C1 . 1.356(2) y
  O1 H1 . 0.92(3) ?
  O10 N1 . 1.268(2) y
  O11 N1 . 1.242(2) y
  O12 N1 . 1.239(2) y
  N7 C12 . 1.505(3) y
  N7 C10 . 1.510(2) y
  N7 C7 . 1.518(3) y
  N7 H7 . 0.89(2) ?
  C1 C6 . 1.391(3) y
  C1 C2 . 1.405(3) y
  C2 C3 . 1.382(3) y
  C2 C7 . 1.495(3) y
  C3 C4 . 1.389(3) y
  C3 H3 . 0.99(2) ?
  C4 C5 . 1.381(3) y
  C4 H4 . 0.92(2) ?
  C5 C6 . 1.385(3) y
  C5 H5 . 0.93(2) ?
  C6 H6 . 0.95(2) ?
  C7 H7A . 0.97(2) ?
  C7 H7B . 0.99(2) ?
  C10 C11 . 1.501(3) y
  C10 H10A . 0.99(3) ?
  C10 H10B . 0.96(2) ?
  C11 H11A . 0.99(3) ?
  C11 H11B . 1.05(3) ?
  C11 H11C . 0.99(3) ?
  C12 C13 . 1.511(3) y
  C12 H12A . 0.96(2) ?
  C12 H12B . 0.97(2) ?
  C13 H13A . 1.01(3) ?
  C13 H13B . 0.96(3) ?
  C13 H13C . 0.99(3) ?