#------------------------------------------------------------------------------
#$Date: 2008-01-26 15:05:32 +0200 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2014371.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_2014371
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2006
_journal_volume  62
_journal_page_first  o58
_journal_page_last  o61
_publ_section_title
;
Hydrogen bonding and \p--\p stacking in
7-{2-[4-(4-methoxyphenyl)piperazin-1-yl]ethoxy}-4-methyl-2<i>H</i>-chromen-2-one
monohydrate
;
loop_
_publ_author_name
  ' Xiang Zhou'
  ' Xiao-Bing Wang'
  ' Ling-Yi Kong'
_chemical_formula_moiety  'C23 H26 N2 O4, H2 O'
_chemical_formula_sum  'C23 H28 N2 O5'
_chemical_formula_iupac  'C23 H26 N2 O4, H2 O'
_chemical_formula_weight  412.47
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  10.776(7)
_cell_length_b  7.483(5)
_cell_length_c  26.381(18)
_cell_angle_alpha  90.00
_cell_angle_beta  99.406(10)
_cell_angle_gamma  90.00
_cell_volume  2099(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  298(2)
_exptl_crystal_density_diffrn  1.305
_diffrn_ambient_temperature  298(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
  N1 0.53174(16) 0.7986(2) 0.12525(6) 0.0505(5) Uani d . 1 . . N
  N2 0.31370(15) 0.8865(2) 0.17170(6) 0.0456(4) Uani d . 1 . . N
  O1 1.17834(14) 0.76897(18) -0.00482(5) 0.0523(4) Uani d . 1 . . O
  O2 1.36372(17) 0.7424(2) -0.02888(6) 0.0759(5) Uani d . 1 . . O
  O3 0.80421(14) 0.8368(2) 0.05953(6) 0.0619(4) Uani d . 1 . . O
  O4 -0.15187(14) 0.9134(2) 0.23986(6) 0.0660(5) Uani d . 1 . . O
  O5 0.47771(17) 0.4188(2) 0.09991(7) 0.0875(6) Uani d D 1 . . O
  H5A 0.4900 0.5342 0.1045 0.105 Uiso d RD 1 . . H
  H5B 0.5127 0.4031 0.0728 0.105 Uiso d RD 1 . . H
  C1 1.2518(2) 0.7162(3) -0.04013(8) 0.0562(6) Uani d . 1 . . C
  C2 1.1882(2) 0.6361(3) -0.08669(8) 0.0579(6) Uani d . 1 . . C
  H2 1.2357 0.6023 -0.1116 0.069 Uiso calc R 1 . . H
  C3 1.0639(2) 0.6078(3) -0.09596(7) 0.0526(6) Uani d . 1 . . C
  C4 0.9889(2) 0.6635(2) -0.05837(7) 0.0454(5) Uani d . 1 . . C
  C5 0.8588(2) 0.6460(3) -0.06280(8) 0.0546(6) Uani d . 1 . . C
  H5 0.8145 0.5948 -0.0925 0.066 Uiso calc R 1 . . H
  C6 0.7934(2) 0.7013(3) -0.02513(8) 0.0541(6) Uani d . 1 . . C
  H6 0.7066 0.6872 -0.0293 0.065 Uiso calc R 1 . . H
  C7 0.8583(2) 0.7787(3) 0.01941(8) 0.0475(5) Uani d . 1 . . C
  C8 0.9869(2) 0.7992(3) 0.02532(7) 0.0470(5) Uani d . 1 . . C
  H8 1.0307 0.8503 0.0551 0.056 Uiso calc R 1 . . H
  C9 1.0498(2) 0.7438(2) -0.01305(7) 0.0443(5) Uani d . 1 . . C
  C10 1.0030(3) 0.5162(3) -0.14454(8) 0.0743(8) Uani d . 1 . . C
  H10A 0.9370 0.5904 -0.1621 0.111 Uiso calc R 1 . . H
  H10B 0.9685 0.4038 -0.1361 0.111 Uiso calc R 1 . . H
  H10C 1.0648 0.4959 -0.1663 0.111 Uiso calc R 1 . . H
  C11 0.6738(2) 0.8042(3) 0.05988(8) 0.0569(6) Uani d . 1 . . C
  H11A 0.6524 0.6810 0.0509 0.068 Uiso calc R 1 . . H
  H11B 0.6219 0.8823 0.0359 0.068 Uiso calc R 1 . . H
  C12 0.6566(2) 0.8438(3) 0.11425(8) 0.0611(6) Uani d . 1 . . C
  H12A 0.7190 0.7775 0.1375 0.073 Uiso calc R 1 . . H
  H12B 0.6718 0.9700 0.1210 0.073 Uiso calc R 1 . . H
  C13 0.5342(2) 0.8006(3) 0.18101(8) 0.0580(6) Uani d . 1 . . C
  H13A 0.5620 0.9172 0.1944 0.070 Uiso calc R 1 . . H
  H13B 0.5945 0.7128 0.1969 0.070 Uiso calc R 1 . . H
  C14 0.4084(2) 0.7606(3) 0.19534(8) 0.0572(6) Uani d . 1 . . C
  H14A 0.3832 0.6403 0.1844 0.069 Uiso calc R 1 . . H
  H14B 0.4145 0.7662 0.2324 0.069 Uiso calc R 1 . . H
  C15 0.3096(2) 0.8845(3) 0.11589(7) 0.0570(6) Uani d . 1 . . C
  H15A 0.2487 0.9719 0.1001 0.068 Uiso calc R 1 . . H
  H15B 0.2823 0.7677 0.1026 0.068 Uiso calc R 1 . . H
  C16 0.4362(2) 0.9263(3) 0.10182(8) 0.0580(6) Uani d . 1 . . C
  H16A 0.4304 0.9226 0.0648 0.070 Uiso calc R 1 . . H
  H16B 0.4612 1.0461 0.1133 0.070 Uiso calc R 1 . . H
  C17 0.19665(19) 0.8838(2) 0.18936(7) 0.0421(5) Uani d . 1 . . C
  C18 0.1749(2) 0.7849(3) 0.23161(7) 0.0508(5) Uani d . 1 . . C
  H18 0.2387 0.7119 0.2483 0.061 Uiso calc R 1 . . H
  C19 0.0613(2) 0.7915(3) 0.24977(7) 0.0517(6) Uani d . 1 . . C
  H19 0.0506 0.7250 0.2785 0.062 Uiso calc R 1 . . H
  C20 -0.0357(2) 0.8961(3) 0.22545(7) 0.0485(5) Uani d . 1 . . C
  C21 -0.0158(2) 0.9946(3) 0.18305(8) 0.0524(6) Uani d . 1 . . C
  H21 -0.0804 1.0653 0.1660 0.063 Uiso calc R 1 . . H
  C22 0.0970(2) 0.9897(3) 0.16589(7) 0.0499(5) Uani d . 1 . . C
  H22 0.1078 1.0590 0.1377 0.060 Uiso calc R 1 . . H
  C23 -0.1775(2) 0.8104(4) 0.28198(9) 0.0760(8) Uani d . 1 . . C
  H23A -0.2593 0.8406 0.2893 0.114 Uiso calc R 1 . . H
  H23B -0.1153 0.8350 0.3116 0.114 Uiso calc R 1 . . H
  H23C -0.1753 0.6857 0.2736 0.114 Uiso calc R 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
  N1 0.0525(11) 0.0517(11) 0.0468(10) -0.0007(9) 0.0067(8) 0.0028(8)
  N2 0.0516(11) 0.0458(10) 0.0379(9) 0.0043(8) 0.0028(8) 0.0063(7)
  O1 0.0602(10) 0.0522(9) 0.0457(8) -0.0058(7) 0.0123(7) -0.0056(7)
  O2 0.0662(12) 0.0896(14) 0.0756(11) -0.0065(10) 0.0226(9) -0.0157(9)
  O3 0.0566(10) 0.0688(11) 0.0625(9) -0.0072(8) 0.0163(8) -0.0108(8)
  O4 0.0641(11) 0.0767(12) 0.0598(9) 0.0069(9) 0.0180(8) 0.0089(8)
  O5 0.0984(14) 0.0706(12) 0.0981(13) -0.0173(10) 0.0296(11) -0.0117(10)
  C1 0.0703(17) 0.0490(14) 0.0525(13) -0.0014(12) 0.0197(13) 0.0026(11)
  C2 0.0834(18) 0.0475(14) 0.0467(13) -0.0015(12) 0.0223(12) -0.0002(10)
  C3 0.0856(18) 0.0316(12) 0.0414(11) -0.0044(11) 0.0125(12) 0.0024(9)
  C4 0.0672(15) 0.0296(11) 0.0384(11) -0.0055(10) 0.0056(10) 0.0040(9)
  C5 0.0731(17) 0.0442(13) 0.0429(12) -0.0119(11) -0.0019(11) 0.0014(10)
  C6 0.0559(14) 0.0512(14) 0.0535(13) -0.0068(11) 0.0035(11) 0.0080(11)
  C7 0.0588(15) 0.0368(12) 0.0471(12) -0.0017(10) 0.0091(11) 0.0041(9)
  C8 0.0569(14) 0.0434(13) 0.0399(11) -0.0034(10) 0.0054(10) -0.0015(9)
  C9 0.0547(14) 0.0322(11) 0.0451(11) -0.0045(9) 0.0058(10) 0.0061(9)
  C10 0.110(2) 0.0630(16) 0.0500(13) -0.0117(15) 0.0134(14) -0.0141(12)
  C11 0.0513(14) 0.0566(14) 0.0628(14) -0.0044(11) 0.0090(11) 0.0024(11)
  C12 0.0591(15) 0.0631(16) 0.0614(14) -0.0040(12) 0.0111(12) -0.0027(12)
  C13 0.0578(15) 0.0645(15) 0.0488(12) 0.0065(12) 0.0001(11) 0.0042(11)
  C14 0.0591(14) 0.0654(15) 0.0452(11) 0.0092(12) 0.0033(11) 0.0141(11)
  C15 0.0580(14) 0.0681(15) 0.0434(12) 0.0072(12) 0.0038(10) 0.0107(11)
  C16 0.0637(15) 0.0589(15) 0.0519(13) 0.0050(12) 0.0114(11) 0.0132(11)
  C17 0.0514(13) 0.0349(11) 0.0380(10) -0.0017(10) 0.0013(10) -0.0010(9)
  C18 0.0602(14) 0.0445(13) 0.0451(12) 0.0035(11) 0.0007(11) 0.0076(10)
  C19 0.0648(15) 0.0491(13) 0.0410(11) -0.0030(11) 0.0082(11) 0.0064(10)
  C20 0.0547(14) 0.0456(13) 0.0442(11) -0.0021(11) 0.0054(11) -0.0041(10)
  C21 0.0592(15) 0.0455(13) 0.0507(12) 0.0092(11) 0.0035(11) 0.0043(10)
  C22 0.0630(15) 0.0429(12) 0.0428(11) 0.0038(11) 0.0055(11) 0.0075(10)
  C23 0.0715(17) 0.096(2) 0.0632(15) -0.0050(15) 0.0203(13) 0.0125(14)
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
  N1 C16 . 1.465(3) yes
  N1 C12 . 1.461(3) yes
  N1 C13 . 1.467(3) yes
  N2 C17 . 1.414(3) yes
  N2 C14 . 1.452(2) yes
  N2 C15 . 1.466(3) yes
  O1 C1 . 1.375(3) ?
  O1 C9 . 1.380(3) ?
  O2 C1 . 1.210(3) ?
  O3 C7 . 1.360(2) ?
  O3 C11 . 1.428(3) ?
  O4 C20 . 1.373(2) ?
  O4 C23 . 1.416(3) ?
  O5 H5A . 0.8786 ?
  O5 H5B . 0.8689 ?
  C1 C2 . 1.436(3) ?
  C2 C3 . 1.338(3) ?
  C2 H2 . 0.9300 ?
  C3 C4 . 1.440(3) ?
  C3 C10 . 1.506(3) ?
  C4 C5 . 1.394(3) ?
  C4 C9 . 1.401(3) ?
  C5 C6 . 1.373(3) ?
  C5 H5 . 0.9300 ?
  C6 C7 . 1.391(3) ?
  C6 H6 . 0.9300 ?
  C7 C8 . 1.378(3) ?
  C8 C9 . 1.371(3) ?
  C8 H8 . 0.9300 ?
  C10 H10A . 0.9600 ?
  C10 H10B . 0.9600 ?
  C10 H10C . 0.9600 ?
  C11 C12 . 1.505(3) ?
  C11 H11A . 0.9700 ?
  C11 H11B . 0.9700 ?
  C12 H12A . 0.9700 ?
  C12 H12B . 0.9700 ?
  C13 C14 . 1.496(3) yes
  C13 H13A . 0.9700 ?
  C13 H13B . 0.9700 ?
  C14 H14A . 0.9700 ?
  C14 H14B . 0.9700 ?
  C15 C16 . 1.505(3) yes
  C15 H15A . 0.9700 ?
  C15 H15B . 0.9700 ?
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C17 C18 . 1.389(3) ?
  C17 C22 . 1.395(3) ?
  C18 C19 . 1.386(3) ?
  C18 H18 . 0.9300 ?
  C19 C20 . 1.377(3) ?
  C19 H19 . 0.9300 ?
  C20 C21 . 1.385(3) ?
  C21 C22 . 1.365(3) ?
  C21 H21 . 0.9300 ?
  C22 H22 . 0.9300 ?
  C23 H23A . 0.9600 ?
  C23 H23B . 0.9600 ?
  C23 H23C . 0.9600 ?