data_2013219
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o62
_journal_page_last  o64
_publ_section_title
;
The solid dihydrate of N,N-dimethyl-n-tetradecylamine oxide
;
loop_
_publ_author_name
  'Sauer, Joe D.'
  'Elnagar, Hassan Y.'
  'Fronczek, Frank R.'
_chemical_formula_moiety  'C16 H35 N O, 2H2 O'
_chemical_formula_sum  'C16 H39 N O3'
_chemical_formula_iupac  'C16 H35 N O, 2H2 O'
_chemical_formula_weight  293.48
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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  22.782(8)
_cell_length_b  8.110(5)
_cell_length_c  9.995(5)
_cell_angle_alpha  90
_cell_angle_beta  91.19(2)
_cell_angle_gamma  90
_cell_volume  1846.3(16)
_cell_formula_units_Z  4
_cell_measurement_temperature  100
_exptl_crystal_density_diffrn  1.056
_diffrn_ambient_temperature  100
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
  O1 0.91337(10) 0.6352(3) 0.16990(19) 0.0342(6) Uani d . 1 . . O
  N1 0.89780(12) 0.6766(3) 0.3016(2) 0.0285(7) Uani d . 1 . . N
  C1 0.83330(14) 0.6461(5) 0.3101(3) 0.0319(9) Uani d . 1 . . C
  H1A 0.8252 0.5332 0.2769 0.038 Uiso calc R 1 . . H
  H1B 0.8129 0.7236 0.2484 0.038 Uiso calc R 1 . . H
  C2 0.80611(14) 0.6631(5) 0.4477(3) 0.0339(9) Uani d . 1 . . C
  H2A 0.8209 0.5744 0.5075 0.041 Uiso calc R 1 . . H
  H2B 0.8173 0.7705 0.4878 0.041 Uiso calc R 1 . . H
  C3 0.73959(14) 0.6518(5) 0.4337(3) 0.0344(9) Uani d . 1 . . C
  H3A 0.7255 0.7439 0.3765 0.041 Uiso calc R 1 . . H
  H3B 0.7294 0.5477 0.3871 0.041 Uiso calc R 1 . . H
  C4 0.70723(14) 0.6574(5) 0.5651(3) 0.0328(9) Uani d . 1 . . C
  H4A 0.7208 0.5644 0.6220 0.039 Uiso calc R 1 . . H
  H4B 0.7176 0.7610 0.6124 0.039 Uiso calc R 1 . . H
  C5 0.64094(14) 0.6479(5) 0.5482(3) 0.0336(9) Uani d . 1 . . C
  H5A 0.6308 0.5453 0.4992 0.040 Uiso calc R 1 . . H
  H5B 0.6275 0.7419 0.4922 0.040 Uiso calc R 1 . . H
  C6 0.60755(14) 0.6505(5) 0.6782(3) 0.0323(9) Uani d . 1 . . C
  H6A 0.6200 0.5546 0.7331 0.039 Uiso calc R 1 . . H
  H6B 0.6184 0.7515 0.7284 0.039 Uiso calc R 1 . . H
  C7 0.54145(14) 0.6458(5) 0.6594(3) 0.0335(9) Uani d . 1 . . C
  H7A 0.5307 0.5454 0.6082 0.040 Uiso calc R 1 . . H
  H7B 0.5291 0.7422 0.6049 0.040 Uiso calc R 1 . . H
  C8 0.50745(14) 0.6468(5) 0.7886(3) 0.0332(9) Uani d . 1 . . C
  H8A 0.5189 0.5485 0.8417 0.040 Uiso calc R 1 . . H
  H8B 0.5191 0.7454 0.8411 0.040 Uiso calc R 1 . . H
  C9 0.44146(14) 0.6474(5) 0.7696(3) 0.0344(9) Uani d . 1 . . C
  H9A 0.4299 0.5492 0.7166 0.041 Uiso calc R 1 . . H
  H9B 0.4301 0.7461 0.7169 0.041 Uiso calc R 1 . . H
  C10 0.40740(14) 0.6475(5) 0.8981(3) 0.0329(9) Uani d . 1 . . C
  H10A 0.4197 0.7443 0.9521 0.040 Uiso calc R 1 . . H
  H10B 0.4181 0.5474 0.9498 0.040 Uiso calc R 1 . . H
  C11 0.34122(14) 0.6522(5) 0.8792(3) 0.0334(9) Uani d . 1 . . C
  H11A 0.3306 0.7524 0.8275 0.040 Uiso calc R 1 . . H
  H11B 0.3289 0.5555 0.8251 0.040 Uiso calc R 1 . . H
  C12 0.30721(14) 0.6521(5) 1.0078(3) 0.0327(9) Uani d . 1 . . C
  H12A 0.3203 0.7472 1.0629 0.039 Uiso calc R 1 . . H
  H12B 0.3171 0.5505 1.0584 0.039 Uiso calc R 1 . . H
  C13 0.24111(14) 0.6610(5) 0.9887(3) 0.0351(9) Uani d . 1 . . C
  H13A 0.2279 0.5653 0.9345 0.042 Uiso calc R 1 . . H
  H13B 0.2312 0.7620 0.9374 0.042 Uiso calc R 1 . . H
  C14 0.20739(15) 0.6627(5) 1.1185(3) 0.0387(10) Uani d . 1 . . C
  H14A 0.2147 0.5596 1.1673 0.058 Uiso calc R 1 . . H
  H14B 0.1653 0.6732 1.0982 0.058 Uiso calc R 1 . . H
  H14C 0.2204 0.7562 1.1736 0.058 Uiso calc R 1 . . H
  C15 0.93178(15) 0.5730(5) 0.3988(3) 0.0357(9) Uani d . 1 . . C
  H15A 0.9215 0.4568 0.3854 0.054 Uiso calc R 1 . . H
  H15B 0.9223 0.6060 0.4902 0.054 Uiso calc R 1 . . H
  H15C 0.9739 0.5882 0.3849 0.054 Uiso calc R 1 . . H
  C16 0.91250(15) 0.8520(4) 0.3237(3) 0.0338(9) Uani d . 1 . . C
  H16A 0.9548 0.8683 0.3129 0.051 Uiso calc R 1 . . H
  H16B 0.9017 0.8841 0.4145 0.051 Uiso calc R 1 . . H
  H16C 0.8908 0.9201 0.2585 0.051 Uiso calc R 1 . . H
  O1W 1.03069(11) 0.6873(3) 0.1416(2) 0.0406(7) Uani d D 1 . . O
  H1W 0.9922 0.674 0.146 0.061 Uiso d D 1 . . H
  H2W 1.0440 0.679 0.0607 0.061 Uiso d D 1 . . H
  O2W 0.91913(12) 0.3044(4) 0.1151(2) 0.0466(8) Uani d D 1 . . O
  H3W 0.9160 0.4099 0.132 0.070 Uiso d D 1 . . H
  H4W 0.9203 0.2420 0.187 0.070 Uiso d 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 0.0387(14) 0.0462(17) 0.0181(12) 0.0024(13) 0.0081(10) -0.0031(11)
  N1 0.0320(17) 0.0320(18) 0.0217(15) 0.0022(14) 0.0031(12) -0.0023(13)
  C1 0.031(2) 0.038(2) 0.0258(18) -0.0057(18) -0.0028(14) -0.0030(16)
  C2 0.032(2) 0.050(3) 0.0203(17) -0.0034(19) 0.0032(14) -0.0031(17)
  C3 0.031(2) 0.049(3) 0.0227(18) -0.0026(19) 0.0005(14) -0.0023(17)
  C4 0.031(2) 0.042(2) 0.0244(18) 0.0005(19) 0.0008(14) -0.0034(17)
  C5 0.029(2) 0.046(2) 0.0251(18) -0.0029(19) -0.0008(15) -0.0009(17)
  C6 0.032(2) 0.043(2) 0.0223(17) 0.0004(19) 0.0011(14) 0.0014(17)
  C7 0.030(2) 0.045(2) 0.0256(18) -0.0023(19) -0.0003(14) -0.0043(17)
  C8 0.031(2) 0.045(2) 0.0231(18) 0.0031(19) 0.0016(14) 0.0004(17)
  C9 0.033(2) 0.045(3) 0.0249(18) -0.0034(19) -0.0002(15) 0.0004(18)
  C10 0.031(2) 0.045(2) 0.0224(18) -0.0010(18) 0.0003(14) -0.0005(17)
  C11 0.029(2) 0.044(2) 0.0272(18) -0.0049(19) 0.0010(14) -0.0007(17)
  C12 0.032(2) 0.043(2) 0.0231(18) -0.0007(19) 0.0013(14) 0.0007(17)
  C13 0.031(2) 0.045(2) 0.0289(19) -0.0029(19) -0.0030(15) 0.0016(18)
  C14 0.036(2) 0.050(3) 0.0304(19) -0.001(2) 0.0037(16) 0.0013(19)
  C15 0.039(2) 0.041(2) 0.0274(19) 0.0105(19) -0.0001(16) 0.0006(17)
  C16 0.036(2) 0.036(2) 0.0291(19) -0.0029(18) 0.0082(15) -0.0017(17)
  O1W 0.0383(15) 0.0506(17) 0.0330(14) -0.0010(14) 0.0064(12) -0.0041(13)
  O2W 0.0541(18) 0.0551(19) 0.0307(14) 0.0100(16) -0.0024(12) -0.0096(13)
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 N1 . 1.411(3) y
  N1 C16 . 1.477(4) y
  N1 C15 . 1.489(4) y
  N1 C1 . 1.494(4) y
  C1 C2 . 1.526(4) ?
  C1 H1A . 0.9900 ?
  C1 H1B . 0.9900 ?
  C2 C3 . 1.522(4) ?
  C2 H2A . 0.9900 ?
  C2 H2B . 0.9900 ?
  C3 C4 . 1.520(4) ?
  C3 H3A . 0.9900 ?
  C3 H3B . 0.9900 ?
  C4 C5 . 1.518(4) ?
  C4 H4A . 0.9900 ?
  C4 H4B . 0.9900 ?
  C5 C6 . 1.519(4) ?
  C5 H5A . 0.9900 ?
  C5 H5B . 0.9900 ?
  C6 C7 . 1.514(4) ?
  C6 H6A . 0.9900 ?
  C6 H6B . 0.9900 ?
  C7 C8 . 1.520(4) ?
  C7 H7A . 0.9900 ?
  C7 H7B . 0.9900 ?
  C8 C9 . 1.512(4) ?
  C8 H8A . 0.9900 ?
  C8 H8B . 0.9900 ?
  C9 C10 . 1.514(4) ?
  C9 H9A . 0.9900 ?
  C9 H9B . 0.9900 ?
  C10 C11 . 1.516(4) ?
  C10 H10A . 0.9900 ?
  C10 H10B . 0.9900 ?
  C11 C12 . 1.515(4) ?
  C11 H11A . 0.9900 ?
  C11 H11B . 0.9900 ?
  C12 C13 . 1.516(4) ?
  C12 H12A . 0.9900 ?
  C12 H12B . 0.9900 ?
  C13 C14 . 1.522(4) ?
  C13 H13A . 0.9900 ?
  C13 H13B . 0.9900 ?
  C14 H14A . 0.9800 ?
  C14 H14B . 0.9800 ?
  C14 H14C . 0.9800 ?
  C15 H15A . 0.9800 ?
  C15 H15B . 0.9800 ?
  C15 H15C . 0.9800 ?
  C16 H16A . 0.9800 ?
  C16 H16B . 0.9800 ?
  C16 H16C . 0.9800 ?
  O1W H1W . 0.88 ?
  O1W H2W . 0.87 ?
  O2W H3W . 0.88 ?
  O2W H4W . 0.88 ?