#------------------------------------------------------------------------------
#$Date: 2008-11-20 19:58:43 +0000 (Thu, 20 Nov 2008) $
#$Revision: 481 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006185.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_2006185
_journal_name_full 'Acta Crystallographica Section C'
_journal_year 1997
_journal_volume 53
_journal_page_first 799
_journal_page_last 801
_publ_section_title
;
10H^+^-2,3-Benzo-1,4-dioxa-7,10,13-triazacyclopentadec-2-ene-6,14-dione
Picrate Hydrate (1:1:1)
;
loop_
_publ_author_name
 'Hundal, Geeta'
 'Kumar, Subodh'
 'Hundal, Maninder Singh'
 'Singh, Harjit'
 'Sanz-Aparicio, Julia'
 'Martinez-Ripoll, Martin'
_chemical_formula_moiety 'C14 H20 N3 O4 +, C6 H2 N3 O7 -, H2 O'
_chemical_formula_sum 'C20 H24 N6 O12'
_chemical_formula_weight 540.45
_symmetry_cell_setting orthorhombic
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
_cell_length_a 7.4948(3)
_cell_length_b 11.5989(6)
_cell_length_c 27.147(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2359.9(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_exptl_crystal_density_diffrn 1.521
_diffrn_ambient_temperature 293(2)
_refine_ls_R_factor_obs  .0399
_refine_ls_wR_factor_obs  .0997
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
 O1  .2624(5)  -.0427(3)  .53565(12)  .0527(9) Uani d . 1 . O
 O2  -.0180(8)  .1204(5)  .5365(2)  .105(2) Uani d . 1 . O
 O3  .1174(10)  .2375(4)  .5843(2)  .110(2) Uani d . 1 . O
 O4  .0269(5)  .0450(3)  .75230(12)  .0584(10) Uani d . 1 . O
 O5  .1285(6)  -.1286(4)  .75876(12)  .0673(11) Uani d . 1 . O
 O6  .3270(5)  -.3317(3)  .61572(14)  .0570(9) Uani d . 1 . O
 O7  .4563(5)  -.2300(3)  .55975(12)  .0504(8) Uani d . 1 . O
 O8  .4454(4)  .0676(3)  .31189(11)  .0468(8) Uani d . 1 . O
 O9  .1227(4)  .1279(3)  .40404(14)  .0518(8) Uani d . 1 . O
 O10  .8231(5)  -.3200(3)  .40290(15)  .0573(9) Uani d . 1 . O
 O11  .6280(5)  -.1232(3)  .32041(11)  .0466(8) Uani d . 1 . O
 N1  .0700(7)  .1425(4)  .5733(2)  .0571(12) Uani d . 1 . N
 N2  .0936(5)  -.0420(4)  .73423(14)  .0453(10) Uani d . 1 . N
 N3  .3555(5)  -.2390(3)  .59539(13)  .0399(8) Uani d . 1 . N
 N4  .4228(4)  .1204(3)  .40567(13)  .0335(7) Uani d . 1 . N
 N5  .5573(5)  -.0482(3)  .47709(12)  .0338(8) Uani d . 1 . N
 N6  .8045(5)  -.1239(3)  .40205(14)  .0381(8) Uani d . 1 . N
 C1  .2247(6)  -.0454(4)  .5801(2)  .0364(9) Uani d . 1 . C
 C2  .1263(6)  .0458(4)  .6042(2)  .0394(10) Uani d . 1 . C
 C3  .0851(6)  .0493(4)  .6532(2)  .0425(10) Uani d . 1 . C
 H3A  .0235(6)  .1142(4)  .6671(2)  .080 Uiso d R 1 . H
 C4  .1328(6)  -.0435(4)  .6826(2)  .0386(10) Uani d . 1 . C
 C5  .2209(6)  -.1376(4)  .6627(2)  .0389(10) Uani d . 1 . C
 H5A  .2487(6)  -.2032(4)  .6828(2)  .080 Uiso d R 1 . H
 C6  .2658(6)  -.1373(4)  .6136(2)  .0349(9) Uani d . 1 . C
 C7  .4603(6)  -.0001(4)  .2708(2)  .0392(10) Uani d . 1 . C
 C8  .2708(6)  .0910(4)  .3283(2)  .0463(11) Uani d . 1 . C
 H8A  .1965(6)  .0255(4)  .3215(2)  .080 Uiso d R 1 . H
 H8B  .2231(6)  .1560(4)  .3108(2)  .080 Uiso d R 1 . H
 C9  .2684(6)  .1150(4)  .3827(2)  .0386(10) Uani d . 1 . C
 C10  .4365(6)  .1453(4)  .4580(2)  .0375(10) Uani d . 1 . C
 H10A  .3272(6)  .1248(4)  .4742(2)  .080 Uiso d R 1 . H
 H10B  .4559(6)  .2264(4)  .4627(2)  .080 Uiso d R 1 . H
 C11  .5874(6)  .0789(3)  .4806(2)  .0388(10) Uani d . 1 . C
 H11A  .6957(6)  .0976(3)  .4634(2)  .080 Uiso d R 1 . H
 H11B  .6017(6)  .1009(3)  .5144(2)  .080 Uiso d R 1 . H
 C12  .7180(6)  -.1191(4)  .4896(2)  .0380(10) Uani d . 1 . C
 H12A  .6841(6)  -.1987(4)  .4918(2)  .080 Uiso d R 1 . H
 H12B  .7616(6)  -.0957(4)  .5213(2)  .080 Uiso d R 1 . H
 C13  .8688(6)  -.1065(4)  .4516(2)  .0421(10) Uani d . 1 . C
 H13A  .9196(6)  -.0307(4)  .4541(2)  .080 Uiso d R 1 . H
 H13B  .9612(6)  -.1615(4)  .4585(2)  .080 Uiso d R 1 . H
 C14  .7843(6)  -.2286(4)  .3822(2)  .0407(10) Uani d . 1 . C
 C15  .7131(6)  -.2292(4)  .3296(2)  .0423(10) Uani d . 1 . C
 H15A  .8102(6)  -.2394(4)  .3070(2)  .080 Uiso d R 1 . H
 H15B  .6306(6)  -.2916(4)  .3251(2)  .080 Uiso d R 1 . H
 C16  .5602(6)  -.1010(4)  .2744(2)  .0385(10) Uani d . 1 . C
 C17  .5844(7)  -.1705(4)  .2333(2)  .0466(11) Uani d . 1 . C
 H17A  .6529(7)  -.2402(4)  .2355(2)  .080 Uiso d R 1 . H
 C18  .5061(8)  -.1378(5)  .1889(2)  .0526(13) Uani d . 1 . C
 H18A  .5241(8)  -.1848(5)  .1602(2)  .080 Uiso d R 1 . H
 C19  .4064(7)  -.0400(5)  .1852(2)  .0529(13) Uani d . 1 . C
 H19A  .3520(7)  -.0200(5)  .1544(2)  .080 Uiso d R 1 . H
 C20  .3828(7)  .0303(5)  .2264(2)  .0505(12) Uani d . 1 . C
 H20A  .3126(7)  .0993(5)  .2240(2)  .080 Uiso d R 1 . H
 H61  .7788(7)  -.0603(5)  .3805(2)  .050 Uiso d R 1 . H
 H51  .4540(7)  -.0712(5)  .4999(2)  .050 Uiso d R 1 . H
 H52  .5215(7)  -.0619(5)  .4504(2)  .500 Uiso d R 1 . H
 H41  .5285(7)  .1190(5)  .3903(2)  .050 Uiso d R 1 . H
 O12  .7923(4)  .1105(3)  .36534(12)  .0435(7) Uani d . 1 . O
 H122  .8871(4)  .1217(3)  .38059(12)  .050 Uiso d R 1 . H
 H121  .8070(4)  .1231(3)  .33059(12)  .050 Uiso d 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
 O1  .058(2)  .067(2)  .033(2)  .015(2)  .011(2)  .012(2)
 O2  .135(5)  .097(4)  .083(3)  .035(3)  -.042(4)  .018(3)
 O3  .193(7)  .051(3)  .086(3)  .007(3)  .012(4)  .016(2)
 O4  .063(2)  .071(2)  .041(2)  -.007(2)  .014(2)  -.013(2)
 O5  .092(3)  .077(3)  .033(2)  .001(2)  .005(2)  .012(2)
 O6  .061(2)  .042(2)  .067(2)  .011(2)  .006(2)  .013(2)
 O7  .051(2)  .055(2)  .046(2)  .005(2)  .009(2)  -.004(2)
 O8  .034(2)  .066(2)  .041(2)  .005(2)  -.0053(14)  -.015(2)
 O9  .030(2)  .072(2)  .053(2)  .0032(15)  .004(2)  -.008(2)
 O10  .069(2)  .044(2)  .058(2)  .012(2)  .000(2)  .008(2)
 O11  .060(2)  .048(2)  .032(2)  .012(2)  -.0049(14)  -.0016(13)
 N1  .083(3)  .042(2)  .047(2)  .016(2)  .016(2)  .008(2)
 N2  .047(2)  .058(3)  .031(2)  -.013(2)  .003(2)  -.001(2)
 N3  .036(2)  .047(2)  .037(2)  .002(2)  -.004(2)  .003(2)
 N4  .031(2)  .038(2)  .031(2)  .0047(15)  .002(2)  .0009(15)
 N5  .031(2)  .038(2)  .032(2)  .0016(14)  .0034(15)  .003(2)
 N6  .042(2)  .039(2)  .033(2)  .007(2)  .001(2)  .003(2)
 C1  .036(2)  .041(2)  .032(2)  -.002(2)  .004(2)  .006(2)
 C2  .045(2)  .038(2)  .035(2)  .000(2)  .006(2)  .003(2)
 C3  .047(2)  .041(2)  .039(2)  -.005(2)  .005(2)  -.005(2)
 C4  .042(2)  .045(2)  .028(2)  -.008(2)  .003(2)  .001(2)
 C5  .044(2)  .042(2)  .031(2)  -.008(2)  -.006(2)  .004(2)
 C6  .033(2)  .038(2)  .033(2)  .001(2)  -.001(2)  -.002(2)
 C7  .036(2)  .050(2)  .032(2)  -.005(2)  .001(2)  -.004(2)
 C8  .036(2)  .057(3)  .046(3)  .006(2)  -.007(2)  -.012(2)
 C9  .035(2)  .034(2)  .047(2)  .004(2)  -.001(2)  .001(2)
 C10  .040(2)  .037(2)  .035(2)  .005(2)  -.004(2)  -.002(2)
 C11  .047(3)  .034(2)  .035(2)  -.001(2)  -.006(2)  -.003(2)
 C12  .041(2)  .039(2)  .034(2)  .007(2)  -.001(2)  .003(2)
 C13  .038(2)  .049(3)  .039(2)  .008(2)  -.004(2)  .004(2)
 C14  .037(2)  .043(2)  .042(2)  .006(2)  .009(2)  .005(2)
 C15  .042(2)  .044(2)  .042(2)  .009(2)  .003(2)  -.001(2)
 C16  .041(2)  .048(2)  .027(2)  -.012(2)  .002(2)  .000(2)
 C17  .054(3)  .048(3)  .039(2)  -.011(2)  .006(2)  -.006(2)
 C18  .069(3)  .060(3)  .029(2)  -.024(3)  .001(2)  -.008(2)
 C19  .049(3)  .076(4)  .034(2)  -.013(3)  -.010(2)  .004(2)
 C20  .044(3)  .065(3)  .043(3)  .000(2)  -.007(2)  .003(2)
 O12  .0350(15)  .058(2)  .038(2)  -.0047(14)  -.0014(13)  -.0013(15)
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 . 1.240(5) NO
 O2 N1 . 1.225(7) NO
 O3 N1 . 1.195(7) NO
 O4 N2 . 1.229(5) NO
 O5 N2 . 1.233(5) NO
 O6 N3 . 1.227(5) NO
 O7 N3 . 1.232(5) NO
 O8 C7 . 1.369(5) NO
 O8 C8 . 1.409(5) NO
 O9 C9 . 1.245(5) NO
 O10 C14 . 1.234(5) NO
 O11 C16 . 1.373(5) NO
 O11 C15 . 1.408(5) NO
 N1 C2 . 1.463(6) NO
 N2 C4 . 1.431(5) NO
 N3 C6 . 1.446(6) NO
 N4 C9 . 1.316(6) NO
 N4 C10 . 1.453(5) NO
 N4 H41 .  .896(6) ?
 N5 C11 . 1.494(5) NO
 N5 C12 . 1.497(5) NO
 N5 H51 . 1.026(6) ?
 N5 H52 .  .790(6) ?
 N6 C14 . 1.337(6) NO
 N6 C13 . 1.443(6) NO
 N6 H61 .  .962(6) ?
 C1 C6 . 1.434(6) NO
 C1 C2 . 1.447(6) NO
 C2 C3 . 1.366(6) NO
 C3 C4 . 1.387(6) NO
 C3 H3A .  .96 ?
 C4 C5 . 1.385(6) NO
 C5 C6 . 1.374(6) NO
 C5 H5A .  .96 ?
 C7 C20 . 1.383(7) NO
 C7 C16 . 1.393(7) NO
 C8 C9 . 1.504(7) NO
 C8 H8A .  .96 ?
 C8 H8B .  .96 ?
 C10 C11 . 1.499(6) NO
 C10 H10A .  .96 ?
 C10 H10B .  .96 ?
 C11 H11A .  .96 ?
 C11 H11B .  .96 ?
 C12 C13 . 1.538(6) NO
 C12 H12A .  .96 ?
 C12 H12B .  .96 ?
 C13 H13A .  .96 ?
 C13 H13B .  .96 ?
 C14 C15 . 1.525(6) NO
 C15 H15A .  .96 ?
 C15 H15B .  .96 ?
 C16 C17 . 1.387(6) NO
 C17 C18 . 1.395(7) NO
 C17 H17A .  .96 ?
 C18 C19 . 1.361(8) NO
 C18 H18A .  .96 ?
 C19 C20 . 1.395(7) NO
 C19 H19A .  .96 ?
 C20 H20A .  .96 ?
 O12 H122 .  .83 ?
 O12 H121 .  .96 ?