#------------------------------------------------------------------------------
#$Date: 2008-11-20 21:58:43 +0200 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008082.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_2008082
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  94
_journal_page_last  97
_publ_section_title
;
2-Hydroxy-5-methyl-3-(morpholinomethyl)benzaldehyde (I) and
 4,4'-dimethyl-6,6'-bis(morpholinomethyl)-2,2'-ethylene
dinitrilodimethylidyne)diphenol (II)
;
loop_
_publ_author_name
  'S.Shanmuga Sundara Raj'
  'R.Thirumurugan'
  'G.Shanmugam'
  'Hoong-Kun Fun'
  'J.Manonmani'
  'M.Kandaswamy'
_chemical_formula_sum  'C13 H17 N O3'
_chemical_formula_weight  235.28
_chemical_melting_point  175\%C
_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  5.31720(10)
_cell_length_b  15.3099(3)
_cell_length_c  15.34060(10)
_cell_angle_alpha  90.00
_cell_angle_beta  91.8460(10)
_cell_angle_gamma  90.00
_cell_volume  1248.17(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.252
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  0.0490
_refine_ls_wR_factor_obs  0.1355
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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  C1 0.2447(3) 0.55635(10) 0.20868(9) 0.0442(4) Uani d . 1 . C
  C2 0.4111(3) 0.62699(10) 0.22080(10) 0.0465(4) Uani d . 1 . C
  C3 0.5867(3) 0.62316(12) 0.28910(11) 0.0532(4) Uani d . 1 . C
  H3A 0.6999(3) 0.66908(12) 0.29643(11) 0.064 Uiso calc R 1 . H
  C4 0.6014(3) 0.55345(12) 0.34743(10) 0.0551(4) Uani d . 1 . C
  C5 0.4348(3) 0.48554(12) 0.33454(11) 0.0546(4) Uani d . 1 . C
  H5A 0.4414(3) 0.43828(12) 0.37264(11) 0.065 Uiso calc R 1 . H
  C6 0.2559(3) 0.48564(11) 0.26583(10) 0.0487(4) Uani d . 1 . C
  O7 0.0739(2) 0.55552(9) 0.14110(8) 0.0575(3) Uani d . 1 . O
  C8 0.7918(4) 0.5526(2) 0.42251(13) 0.0777(6) Uani d . 1 . C
  H8A 0.8914(4) 0.6049(2) 0.42119(13) 0.117 Uiso calc R 1 . H
  H8B 0.8993(4) 0.5026(2) 0.41757(13) 0.117 Uiso calc R 1 . H
  H8C 0.7060(4) 0.5498(2) 0.47654(13) 0.117 Uiso calc R 1 . H
  C9 0.3906(4) 0.70645(11) 0.16330(12) 0.0576(4) Uani d . 1 . C
  H9A 0.2566(4) 0.74366(11) 0.18331(12) 0.069 Uiso calc R 1 . H
  H9B 0.5466(4) 0.73923(11) 0.16801(12) 0.069 Uiso calc R 1 . H
  N10 0.3389(2) 0.68306(8) 0.07112(8) 0.0476(3) Uani d . 1 . N
  C11 0.5541(3) 0.63968(12) 0.03305(12) 0.0589(5) Uani d . 1 . C
  H11A 0.5971(3) 0.58762(12) 0.06635(12) 0.071 Uiso calc R 1 . H
  H11B 0.6985(3) 0.67846(12) 0.03519(12) 0.071 Uiso calc R 1 . H
  C12 0.4911(5) 0.61535(14) -0.05958(13) 0.0736(6) Uani d . 1 . C
  H12A 0.6339(5) 0.58595(14) -0.08424(13) 0.088 Uiso calc R 1 . H
  H12B 0.3502(5) 0.57508(14) -0.06118(13) 0.088 Uiso calc R 1 . H
  O13 0.4285(3) 0.69024(10) -0.11065(9) 0.0814(5) Uani d . 1 . O
  C14 0.2227(4) 0.73414(15) -0.07489(13) 0.0737(6) Uani d . 1 . C
  H14A 0.0762(4) 0.69641(15) -0.07815(13) 0.088 Uiso calc R 1 . H
  H14B 0.1849(4) 0.78596(15) -0.10924(13) 0.088 Uiso calc R 1 . H
  C15 0.2739(4) 0.76016(11) 0.01821(12) 0.0611(5) Uani d . 1 . C
  H15A 0.4116(4) 0.80171(11) 0.02139(12) 0.073 Uiso calc R 1 . H
  H15B 0.1260(4) 0.78815(11) 0.04095(12) 0.073 Uiso calc R 1 . H
  C16 0.0799(4) 0.41244(14) 0.25634(13) 0.0666(5) Uani d . 1 . C
  H16A -0.0394(4) 0.41415(14) 0.21066(13) 0.080 Uiso calc R 1 . H
  O17 0.0807(3) 0.34995(11) 0.30445(13) 0.0968(6) Uani d . 1 . O
  H7 0.117(5)  0.6036(18) 0.1096(17) 0.100(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
  C1 0.0397(7) 0.0515(8) 0.0412(7) 0.0062(6) 0.0017(6) 0.0002(6)
  C2 0.0502(8) 0.0432(8) 0.0462(8) 0.0052(6) 0.0024(6) -0.0049(6)
  C3 0.0522(9) 0.0572(10) 0.0500(9) -0.0012(7) -0.0014(7) -0.0109(7)
  C4 0.0515(9) 0.0708(11) 0.0426(8) 0.0103(8) -0.0030(7) -0.0046(8)
  C5 0.0579(10) 0.0620(10) 0.0440(8) 0.0101(8) 0.0037(7) 0.0089(7)
  C6 0.0472(8) 0.0533(9) 0.0459(8) 0.0020(7) 0.0055(6) 0.0037(7)
  O7 0.0490(6) 0.0685(8) 0.0542(7) -0.0054(6) -0.0096(5) 0.0116(6)
  C8 0.0666(12) 0.112(2) 0.0537(10) 0.0081(12) -0.0141(9) -0.0056(11)
  C9 0.0712(11) 0.0416(8) 0.0598(10) 0.0045(8) -0.0003(8) -0.0025(7)
  N10 0.0521(7) 0.0399(7) 0.0512(7) 0.0073(6) 0.0057(6) 0.0048(6)
  C11 0.0554(10) 0.0520(10) 0.0699(11) 0.0101(7) 0.0126(8) 0.0056(8)
  C12 0.0955(15) 0.0615(11) 0.0651(12) 0.0157(10) 0.0249(11) 0.0033(9)
  O13 0.1096(12) 0.0743(9) 0.0619(8) 0.0147(8) 0.0293(8) 0.0159(7)
  C14 0.0879(14) 0.0716(13) 0.0623(11) 0.0130(11) 0.0095(10) 0.0218(10)
  C15 0.0703(11) 0.0467(9) 0.0668(11) 0.0127(8) 0.0101(9) 0.0127(8)
  C16 0.0676(12) 0.0662(12) 0.0662(11) -0.0111(9) 0.0026(9) 0.0111(9)
  O17 0.0930(12) 0.0800(10) 0.1173(13) -0.0218(9) 0.0007(10) 0.0409(10)
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 O7 . 1.356(2) yes
  C1 C6 . 1.393(2) ?
  C1 C2 . 1.406(2) ?
  C2 C3 . 1.382(2) ?
  C2 C9 . 1.504(2) ?
  C3 C4 . 1.393(2) ?
  C3 H3A . 0.93 ?
  C4 C5 . 1.376(3) ?
  C4 C8 . 1.509(2) ?
  C5 C6 . 1.397(2) ?
  C5 H5A . 0.93 ?
  C6 C16 . 1.464(3) ?
  O7 H7 . 0.91(3) ?
  C8 H8A . 0.96 ?
  C8 H8B . 0.96 ?
  C8 H8C . 0.96 ?
  C9 N10 . 1.476(2) ?
  C9 H9A . 0.97 ?
  C9 H9B . 0.97 ?
  N10 C11 . 1.461(2) yes
  N10 C15 . 1.468(2) yes
  C11 C12 . 1.496(3) yes
  C11 H11A . 0.97 ?
  C11 H11B . 0.97 ?
  C12 O13 . 1.422(2) yes
  C12 H12A . 0.97 ?
  C12 H12B . 0.97 ?
  O13 C14 . 1.410(2) yes
  C14 C15 . 1.499(3) yes
  C14 H14A . 0.97 ?
  C14 H14B . 0.97 ?
  C15 H15A . 0.97 ?
  C15 H15B . 0.97 ?
  C16 O17 . 1.208(2) yes
  C16 H16A . 0.93 ?