data_2007102
_journal_name_full  'Acta Crystallographica'
_journal_year  1998
_journal_volume  C54
_journal_page_first  415
_journal_page_last  417
_publ_section_title
;
Stereochemistry of Anti-Inflammatory Drugs. VI. Piperazinium
2-(2,6-Dichlorophenylamino)phenylacetate Dihydrate,
(H~2~PZ)D~2~.2H~2~O
;
loop_
_publ_author_name
  'Carlo Castellari'
  'Stefano Ottani'
_chemical_formula_moiety  'C4 H12 N2 2+ , (C14 H10 Cl2 N O2)2 1- , 2H2 O'
_chemical_formula_sum  'C32 H36 Cl4 N4 O6'
_chemical_formula_weight  714.45
_symmetry_cell_setting  'Triclinic'
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  8.897(2)
_cell_length_b  11.242(4)
_cell_length_c  17.13(2)
_cell_angle_alpha  104.46(2)
_cell_angle_beta  93.79(2)
_cell_angle_gamma  90.30(2)
_cell_volume  1655(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.434
_exptl_crystal_density_meas  1.44
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  .0409
_refine_ls_wR_factor_obs  .0913
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
  O3  .0848(3)  .6142(2)  .44830(13)  .0652(6) Uani d D 1 . O
  H17  .029(5)  .538(3)  .430(3)  .126(8) Uiso d D 1 . H
  H18  .025(4)  .651(4)  .492(2)  .126(8) Uiso d D 1 . H
  O3A  .4115(3)  .0855(3)  .4107(2)  .0875(8) Uani d D 1 . O
  H17A  .466(5)  .151(3)  .456(2)  .126(8) Uiso d D 1 . H
  H18A  .511(4)  .045(4)  .403(3)  .126(8) Uiso d D 1 . H
  Cl1  .74460(8) 1.08390(7)  .28049(4)  .0522(2) Uani d D 1 . Cl
  Cl2  .46804(8)  .73934(6)  .03312(4)  .0495(2) Uani d D 1 . Cl
  N1  .5441(2)  .8646(2)  .20915(13)  .0398(5) Uani d D 1 . N
  H1  .587(3)  .879(2)  .2509(14)  .031(7) Uiso d D 1 . H
  C1  .3880(2)  .8498(2)  .21379(13)  .0333(5) Uani d D 1 . C
  C2  .3382(3)  .7725(2)  .25942(13)  .0355(5) Uani d D 1 . C
  C3  .1833(3)  .7547(3)  .2612(2)  .0461(6) Uani d D 1 . C
  H2  .156(3)  .700(2)  .2918(15)  .042(7) Uiso d . 1 . H
  C4  .0807(3)  .8113(3)  .2199(2)  .0518(7) Uani d D 1 . C
  H3  -.023(3)  .799(2)  .2223(15)  .046(7) Uiso d . 1 . H
  C5  .1309(3)  .8888(3)  .1762(2)  .0477(7) Uani d D 1 . C
  H4  .062(3)  .926(2)  .1479(15)  .039(7) Uiso d . 1 . H
  C6  .2832(3)  .9089(2)  .17342(15)  .0402(6) Uani d D 1 . C
  H5  .321(3)  .963(2)  .1464(14)  .033(6) Uiso d . 1 . H
  C7  .6077(3)  .9173(2)  .15309(14)  .0350(5) Uani d D 1 . C
  C8  .7073(3) 1.0183(2)  .17729(14)  .0375(5) Uani d D 1 . C
  C9  .7772(3) 1.0692(3)  .1227(2)  .0449(6) Uani d D 1 . C
  H6  .845(3)  1.139(3)  .1458(16)  .050(8) Uiso d . 1 . H
  C10  .7472(3) 1.0188(3)  .0410(2)  .0500(7) Uani d D 1 . C
  H7  .795(4)  1.056(3)  .0022(19)  .071(10) Uiso d . 1 . H
  C11  .6508(3)  .9188(3)  .0142(2)  .0449(6) Uani d D 1 . C
  H8  .620(3)  .883(2)  -.0421(17)  .048(7) Uiso d . 1 . H
  C12  .5835(3)  .8687(2)  .06952(14)  .0386(5) Uani d D 1 . C
  C13  .4470(3)  .7036(2)  .3020(2)  .0398(6) Uani d D 1 . C
  H9  .520(3)  .664(2)  .2643(16)  .043(7) Uiso d . 1 . H
  H10  .394(3)  .638(3)  .3174(17)  .058(8) Uiso d . 1 . H
  C14  .5320(3)  .7791(2)  .37842(14)  .0385(5) Uani d D 1 . C
  O1  .6067(2)  .8715(2)  .37532(10)  .0477(4) Uani d D 1 . O
  O2  .5275(3)  .7442(2)  .44128(12)  .0808(8) Uani d D 1 . O
  N2  .1415(2)  .0667(2)  .51520(13)  .0362(4) Uani d D 1 . N
  H11  .129(3)  .117(3)  .4813(19)  .062(9) Uiso d . 1 . H
  H12  .233(4)  .083(3)  .5427(18)  .057(9) Uiso d . 1 . H
  C15  .0222(3)  .0951(3)  .5733(2)  .0416(6) Uani d D 1 . C
  H13  .028(3)  .177(3)  .5985(17)  .053(8) Uiso d . 1 . H
  H14  .036(3)  .047(3)  .6107(16)  .047(7) Uiso d . 1 . H
  C16  .1319(3)  -.0638(2)  .4689(2)  .0418(6) Uani d D 1 . C
  H15  .157(3)  -.113(3)  .5082(17)  .051(8) Uiso d . 1 . H
  H16  .208(3)  -.074(3)  .4317(18)  .059(9) Uiso d . 1 . H
  Cl1A  -.17376(8)  .57527(7)  .27937(4)  .0539(2) Uani d D 1 . Cl
  Cl2A  .04040(8)  .24009(6)  .02970(4)  .0488(2) Uani d D 1 . Cl
  N1A  .0098(2)  .3609(2)  .20650(13)  .0385(5) Uani d D 1 . N
  H1A  -.022(3)  .375(3)  .2482(15)  .050(9) Uiso d D 1 . H
  C1A  .1675(3)  .3450(2)  .20902(13)  .0340(5) Uani d D 1 . C
  C2A  .2280(3)  .2622(2)  .25088(13)  .0345(5) Uani d D 1 . C
  C3A  .3824(3)  .2423(3)  .2497(2)  .0444(6) Uani d D 1 . C
  H2A  .421(3)  .181(3)  .2787(17)  .059(8) Uiso d . 1 . H
  C4A  .4748(3)  .3035(3)  .2104(2)  .0509(7) Uani d D 1 . C
  H3A  .573(3)  .290(3)  .2082(16)  .051(8) Uiso d . 1 . H
  C5A  .4144(3)  .3882(3)  .1722(2)  .0489(7) Uani d D 1 . C
  H4A  .473(3)  .432(2)  .1441(16)  .045(7) Uiso d . 1 . H
  C6A  .2620(3)  .4085(3)  .1714(2)  .0423(6) Uani d D 1 . C
  H5A  .221(3)  .462(3)  .1455(16)  .046(8) Uiso d . 1 . H
  C7A  -.0669(3)  .4141(2)  .15127(14)  .0345(5) Uani d D 1 . C
  C8A  -.1618(3)  .5138(2)  .17608(14)  .0376(5) Uani d D 1 . C
  C9A  -.2446(3)  .5647(3)  .1220(2)  .0460(6) Uani d D 1 . C
  H6A  -.301(3)  .636(3)  .1441(16)  .053(8) Uiso d . 1 . H
  C10A  -.2358(3)  .5171(3)  .0406(2)  .0494(7) Uani d D 1 . C
  H7A  -.288(3)  .552(2)  .0047(16)  .047(7) Uiso d . 1 . H
  C11A  -.1461(3)  .4191(3)  .0130(2)  .0442(6) Uani d D 1 . C
  H8A  -.140(3)  .376(3)  -.0416(19)  .063(9) Uiso d . 1 . H
  C12A  -.0654(3)  .3679(2)  .06756(14)  .0369(5) Uani d D 1 . C
  C13A  .1325(3)  .1949(2)  .29641(15)  .0392(6) Uani d D 1 . C
  H9A  .192(3)  .134(3)  .3127(17)  .054(8) Uiso d . 1 . H
  H10A  .040(3)  .159(2)  .2628(16)  .047(7) Uiso d . 1 . H
  C14A  .0669(3)  .2744(2)  .37183(14)  .0395(6) Uani d D 1 . C
  O1A  .0165(3)  .3758(2)  .37045(12)  .0788(8) Uani d D 1 . O
  O2A  .0616(3)  .2320(2)  .43183(12)  .0648(6) Uani d D 1 . O
  N2A  .3740(3)  .5667(2)  .47989(15)  .0535(6) Uani d D 1 . N
  H11A  .257(5)  .585(3)  .470(2)  .089(12) Uiso d . 1 . H
  H12A  .424(3)  .627(3)  .4625(17)  .056(8) Uiso d . 1 . H
  C15A  .4261(4)  .5752(3)  .5666(2)  .0607(8) Uani d D 1 . C
  H13A  .402(4)  .657(4)  .598(2)  .095(12) Uiso d . 1 . H
  H14A  .359(4)  .511(3)  .5758(19)  .068(10) Uiso d . 1 . H
  C16A  .4108(4)  .4480(3)  .4272(2)  .0590(8) Uani d D 1 . C
  H15A  .379(3)  .456(3)  .3732(19)  .063(9) Uiso d . 1 . H
  H16A  .349(4)  .386(3)  .443(2)  .084(11) 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
  O3  .0676(15)  .0663(15)  .0578(13)  .0107(11)  .0135(11)  .0058(11)
  O3A  .096(2)  .097(2)  .062(2)  .031(2)  .0033(13)  .0073(14)
  Cl1  .0494(4)  .0615(4)  .0427(4)  -.0121(3)  -.0043(3)  .0097(3)
  Cl2  .0537(4)  .0468(4)  .0436(3)  -.0052(3)  .0002(3)  .0042(3)
  N1  .0353(11)  .0545(14)  .0325(11)  -.0070(9)  -.0050(9)  .0184(10)
  C1  .0305(12)  .0374(13)  .0286(11)  -.0005(9)  .0007(9)  .0024(9)
  C2  .0364(13)  .0388(13)  .0284(11)  -.0040(10)  .0009(9)  .0036(10)
  C3  .044(2)  .053(2)  .0389(14)  -.0089(12)  .0075(11)  .0055(12)
  C4  .0299(14)  .070(2)  .048(2)  -.0004(13)  .0035(11)  .0009(14)
  C5  .0403(15)  .057(2)  .0388(14)  .0128(13)  -.0049(11)  .0010(12)
  C6  .0433(14)  .0398(14)  .0362(13)  .0029(11)  -.0007(11)  .0083(11)
  C7  .0295(11)  .0413(13)  .0372(12)  .0023(10)  .0004(9)  .0158(10)
  C8  .0300(12)  .0450(14)  .0387(13)  .0017(10)  .0004(10)  .0134(11)
  C9  .0365(14)  .051(2)  .052(2)  -.0047(12)  .0020(11)  .0209(13)
  C10  .045(2)  .064(2)  .050(2)  .0005(13)  .0081(12)  .0297(14)
  C11  .0424(14)  .058(2)  .0368(14)  .0063(13)  .0052(11)  .0170(13)
  C12  .0353(13)  .0414(14)  .0393(13)  .0021(10)  .0005(10)  .0110(11)
  C13  .0455(15)  .0353(14)  .0390(13)  -.0054(11)  -.0017(11)  .0116(11)
  C14  .0415(14)  .0373(14)  .0370(13)  -.0003(11)  -.0030(10)  .0115(11)
  O1  .0523(11)  .0504(11)  .0407(10)  -.0162(9)  -.0103(8)  .0161(8)
  O2  .137(2)  .0652(14)  .0425(12)  -.0424(14)  -.0218(13)  .0260(11)
  N2  .0365(12)  .0379(12)  .0363(11)  -.0013(9)  -.0017(9)  .0143(9)
  C15  .048(2)  .041(2)  .0336(13)  -.0027(12)  .0029(11)  .0060(12)
  C16  .0389(14)  .0400(14)  .0462(15)  .0043(11)  .0051(12)  .0098(12)
  Cl1A  .0555(4)  .0611(5)  .0429(4)  .0149(3)  .0075(3)  .0076(3)
  Cl2A  .0556(4)  .0462(4)  .0411(3)  .0032(3)  .0059(3)  .0040(3)
  N1A  .0392(12)  .0467(13)  .0336(11)  .0061(9)  .0080(9)  .0161(10)
  C1A  .0377(13)  .0358(13)  .0267(11)  -.0001(10)  .0013(9)  .0045(9)
  C2A  .0392(13)  .0330(12)  .0276(11)  .0003(10)  -.0018(9)  .0019(9)
  C3A  .0437(15)  .046(2)  .0394(14)  .0063(12)  -.0024(11)  .0042(12)
  C4A  .0329(14)  .064(2)  .049(2)  .0027(13)  .0024(12)  .0010(14)
  C5A  .044(2)  .055(2)  .0430(15)  -.0134(13)  .0088(12)  .0024(13)
  C6A  .047(2)  .045(2)  .0362(13)  -.0031(12)  .0024(11)  .0125(12)
  C7A  .0315(12)  .0378(13)  .0371(12)  -.0041(9)  .0030(9)  .0146(10)
  C8A  .0340(13)  .0425(14)  .0381(13)  -.0013(10)  .0045(10)  .0129(11)
  C9A  .0395(14)  .049(2)  .054(2)  .0065(12)  .0034(12)  .0216(13)
  C10A  .0408(15)  .065(2)  .051(2)  .0006(13)  -.0030(12)  .0322(15)
  C11A  .0410(14)  .057(2)  .0378(14)  -.0051(12)  -.0001(11)  .0183(13)
  C12A  .0349(12)  .0379(13)  .0383(13)  -.0034(10)  .0042(10)  .0101(10)
  C13A  .050(2)  .0333(13)  .0351(13)  .0034(11)  .0007(11)  .0100(11)
  C14A  .0499(15)  .0364(14)  .0333(12)  .0010(11)  .0013(10)  .0110(10)
  O1A  .154(2)  .0472(13)  .0413(11)  .0392(14)  .0330(13)  .0150(9)
  O2A  .090(2)  .0686(14)  .0501(12)  .0318(12)  .0260(11)  .0361(11)
  N2A  .063(2)  .0487(15)  .0520(14)  -.0042(12)  -.0013(12)  .0207(12)
  C15A  .082(2)  .056(2)  .045(2)  .001(2)  .011(2)  .0128(15)
  C16A  .080(2)  .051(2)  .043(2)  -.012(2)  -.012(2)  .0111(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
  O3 H17 .  .96(2) ?
  O3 H18 .  .95(2) ?
  O3A H17A . 1.02(2) ?
  O3A H18A . 1.00(2) ?
  Cl1 C8 . 1.746(3) ?
  Cl2 C12 . 1.734(3) ?
  N1 C7 . 1.395(3) ?
  N1 C1 . 1.408(3) ?
  N1 H1 .  .77(2) ?
  C1 C6 . 1.393(3) ?
  C1 C2 . 1.394(3) ?
  C2 C3 . 1.395(3) ?
  C2 C13 . 1.505(3) ?
  C3 C4 . 1.373(4) ?
  C3 H2 .  .94(3) ?
  C4 C5 . 1.373(4) ?
  C4 H3 .  .94(3) ?
  C5 C6 . 1.378(4) ?
  C5 H4 .  .92(3) ?
  C6 H5 .  .93(2) ?
  C7 C8 . 1.396(3) ?
  C7 C12 . 1.400(4) ?
  C8 C9 . 1.389(3) ?
  C9 C10 . 1.379(4) ?
  C9 H6 .  .97(3) ?
  C10 C11 . 1.375(4) ?
  C10 H7 .  .98(3) ?
  C11 C12 . 1.382(4) ?
  C11 H8 .  .97(3) ?
  C13 C14 . 1.520(3) ?
  C13 H9 .  .98(3) ?
  C13 H10 .  .97(3) ?
  C14 O2 . 1.237(3) y
  C14 O1 . 1.245(3) y
  N2 C16 . 1.482(3) y
  N2 C15 . 1.485(3) y
  N2 H11 .  .91(3) ?
  N2 H12 .  .91(3) ?
  C15 C16 2_556 1.504(4) ?
  C15 H13 .  .91(3) ?
  C15 H14 .  .94(3) ?
  C16 C15 2_556 1.504(4) y
  C16 H15 .  .99(3) ?
  C16 H16 .  .95(3) ?
  Cl1A C8A . 1.742(3) ?
  Cl2A C12A . 1.732(3) ?
  N1A C7A . 1.385(3) ?
  N1A C1A . 1.414(3) ?
  N1A H1A .  .77(2) ?
  C1A C6A . 1.388(3) ?
  C1A C2A . 1.399(3) ?
  C2A C3A . 1.394(3) ?
  C2A C13A . 1.509(3) ?
  C3A C4A . 1.378(4) ?
  C3A H2A . 1.00(3) ?
  C4A C5A . 1.376(4) ?
  C4A H3A .  .89(3) ?
  C5A C6A . 1.376(4) ?
  C5A H4A .  .95(3) ?
  C6A H5A .  .89(3) ?
  C7A C12A . 1.399(4) ?
  C7A C8A . 1.404(3) ?
  C8A C9A . 1.380(4) ?
  C9A C10A . 1.372(4) ?
  C9A H6A .  .95(3) ?
  C10A C11A . 1.369(4) ?
  C10A H7A .  .91(3) ?
  C11A C12A . 1.381(4) ?
  C11A H8A .  .94(3) ?
  C13A C14A . 1.529(4) ?
  C13A H9A .  .95(3) ?
  C13A H10A . 1.00(3) ?
  C14A O1A . 1.231(3) y
  C14A O2A . 1.240(3) y
  N2A C16A . 1.465(4) y
  N2A C15A . 1.507(4) y
  N2A H11A . 1.07(4) ?
  N2A H12A .  .93(3) ?
  C15A C16A 2_666 1.477(5) y
  C15A H13A .  .98(4) ?
  C15A H14A .  .98(3) ?
  C16A C15A 2_666 1.477(5) ?
  C16A H15A .  .97(3) ?
  C16A H16A .  .99(4) ?