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In the structure of the title compound, CH6N3+·C8H4NO6·H2O, obtained from the reaction of guanidine carbonate with 3-nitro­phthalic acid, the 2-carboxylic acid group is deprotonated and participates in an asymmetric cyclic R21(6) hydrogen-bonding association with the guanidine cation together with a bridging water mol­ecule of solvation. A conjoint R12(7) facial association involving a nitro O-atom acceptor together with a further five guanidinium N—H...O hydrogen bonds, as well as a strong carbox­yl–water O—H...O inter­action [2.528 (3) Å], give a two-dimensional network structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034356/wn2170sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034356/wn2170Isup2.hkl
Contains datablock I

CCDC reference: 659089

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.047
  • wR factor = 0.147
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C2 - C21 ... 1.53 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The structures of the guanidinium salts of nitro-substituted benzoic acids are not numerous in the crystallographic literature. Among these are the 1:1 anhydrous guanidinium salts of 3,5-dinitrosalicylic acid (Smith et al., 2001), 3,5-dinitrobenzoic acid (Smith, Wermuth & White, 2007) and 4-nitroanthranilic acid (a monohydrate) (Smith et al., 2007). The nitro-substituted aromatic dicarboxylic acids provide additional potential for structure extension and some structures of 1:1 Lewis base salts of these acids are known, e.g. the anhydrous compounds of 3-nitrophthalic acid with 3-iodoaniline (Glidewell et al.. 2005) and 4-iodoaniline (Glidewell et al.. 2003 and the dihydrate with brucine (Smith et al., 2005). In the 1:1 dihydrate salt with piperazine (Guo, 2004), the phthalate species is dianionic.

Our 1:1 stoichiometric reaction of 3-nitrophthalic acid with guanidinium carbonate in methanol surprisingly gave good crystals of a hydrated salt guanidinium 2-carboxy-6-nitrobenzoate monohydrate, CH6N3+.C8H4NO6-.H2O, which is reported here. In the title compound, the usual proton transfer occurs from the central (C2) carboxylic acid group which is then involved in a direct hydrogen-bonding interaction with a guanidinium proton (Fig. 1). The guanidinium protons are involved in eight hydrogen bonds with all but one of the available O acceptors (nitro O31B) (Table 1). These include the water molecule of solvation which also provides a bridging link between the two separate carboxylate O-acceptors (O21Ai, O21B: symmetry code (i), x, y, z + 1], extending the structure down the c cell direction. With the guanidinium cation there is an asymmetric cyclic R21(6) (Bernstein et al., 1995) interaction also with a carboxylate O-acceptor together with a conjoint R12(7) nitro-O interaction. The carboxylic acid proton gives a strong hydrogen bond with the water molecule [O···O, 2.528 (2) Å], the overall result being a two-dimensional network structure (Fig. 2).

Within the 3-nitrophthalate anion, the carboxylate group is close to perpendicular to the plane of the benzene ring [C1—C2—C21—O21A, 101.2 (2)°], while the carboxylic acid group is close to coplanar [C2—C1—C11—O11A, 173.34 (19)°]. The nitro group is intermediate between these [C2—3—N31—O31B, 151.2 (2) °]. This conformation is similar to that found in other acid salts of 3-nitrophthalic acid (Smith et al., 2005; Glidewell et al. 2003, 2005). In addition there is an intramolecular aromatic ring hydrogen bond [C6–H···O11A: 2.706 (3) Å] associated with the carboxylic acid group.

Related literature top

For related literature, see: Bernstein et al. (1995); Glidewell et al. (2003, 2005); Guo (2004); Smith et al. (2001, 2005); Smith, Wermuth & White (2007); Smith, Wermuth, Healy & White (2007).

Experimental top

The title compound was synthesized by heating together 1 mmol quantities of 3-nitrophthalic acid and guanidine carbonate in 50 ml of methanol under reflux for 10 minutes. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave colourless crystal prisms (m.p. 395–396 K).

Refinement top

Hydrogen atoms involved in hydrogen-bonding interactions were located by difference methods and their positional and isotropic displacement parameters were refined. The ranges of refined bond lengths were N—H = 0.83 (3)–0.91 (4) Å and O—H = 0.85 (5)–0.89 (4) Å. The aromatic H atoms were included in the refinement in calculated positions (C—H = 0.95 Å) using a riding model approximation, with Uiso(H) = 1.2Ueq(C).

Structure description top

The structures of the guanidinium salts of nitro-substituted benzoic acids are not numerous in the crystallographic literature. Among these are the 1:1 anhydrous guanidinium salts of 3,5-dinitrosalicylic acid (Smith et al., 2001), 3,5-dinitrobenzoic acid (Smith, Wermuth & White, 2007) and 4-nitroanthranilic acid (a monohydrate) (Smith et al., 2007). The nitro-substituted aromatic dicarboxylic acids provide additional potential for structure extension and some structures of 1:1 Lewis base salts of these acids are known, e.g. the anhydrous compounds of 3-nitrophthalic acid with 3-iodoaniline (Glidewell et al.. 2005) and 4-iodoaniline (Glidewell et al.. 2003 and the dihydrate with brucine (Smith et al., 2005). In the 1:1 dihydrate salt with piperazine (Guo, 2004), the phthalate species is dianionic.

Our 1:1 stoichiometric reaction of 3-nitrophthalic acid with guanidinium carbonate in methanol surprisingly gave good crystals of a hydrated salt guanidinium 2-carboxy-6-nitrobenzoate monohydrate, CH6N3+.C8H4NO6-.H2O, which is reported here. In the title compound, the usual proton transfer occurs from the central (C2) carboxylic acid group which is then involved in a direct hydrogen-bonding interaction with a guanidinium proton (Fig. 1). The guanidinium protons are involved in eight hydrogen bonds with all but one of the available O acceptors (nitro O31B) (Table 1). These include the water molecule of solvation which also provides a bridging link between the two separate carboxylate O-acceptors (O21Ai, O21B: symmetry code (i), x, y, z + 1], extending the structure down the c cell direction. With the guanidinium cation there is an asymmetric cyclic R21(6) (Bernstein et al., 1995) interaction also with a carboxylate O-acceptor together with a conjoint R12(7) nitro-O interaction. The carboxylic acid proton gives a strong hydrogen bond with the water molecule [O···O, 2.528 (2) Å], the overall result being a two-dimensional network structure (Fig. 2).

Within the 3-nitrophthalate anion, the carboxylate group is close to perpendicular to the plane of the benzene ring [C1—C2—C21—O21A, 101.2 (2)°], while the carboxylic acid group is close to coplanar [C2—C1—C11—O11A, 173.34 (19)°]. The nitro group is intermediate between these [C2—3—N31—O31B, 151.2 (2) °]. This conformation is similar to that found in other acid salts of 3-nitrophthalic acid (Smith et al., 2005; Glidewell et al. 2003, 2005). In addition there is an intramolecular aromatic ring hydrogen bond [C6–H···O11A: 2.706 (3) Å] associated with the carboxylic acid group.

For related literature, see: Bernstein et al. (1995); Glidewell et al. (2003, 2005); Guo (2004); Smith et al. (2001, 2005); Smith, Wermuth & White (2007); Smith, Wermuth, Healy & White (2007).

Computing details top

Data collection: MSC/AFC Diffractmeter Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractmeter Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom naming scheme for the guanidinium cation, the 3-nitrophthalate anion and the water molecule of solvation in the title compound. Displacement ellipsoids are drawn at the 40% probability level. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The hydrogen-bonded framework structure of the title compound, viewed down the c axial direction, showing hydrogen-bonding associations as dashed lines. For symmetry codes, see Table 1.
guanidinium 2-carboxy-6-nitrobenzoate monohydrate top
Crystal data top
CH6N3+·C8H4NO6·H2OF(000) = 600
Mr = 288.23Dx = 1.528 Mg m3
Monoclinic, P21/cMelting point = 395–396 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 14.758 (3) ÅCell parameters from 25 reflections
b = 12.5955 (19) Åθ = 12.6–17.5°
c = 6.8423 (12) ŵ = 0.13 mm1
β = 100.006 (16)°T = 297 K
V = 1252.5 (4) Å3Cut block, colourless
Z = 40.40 × 0.35 × 0.20 mm
Data collection top
Rigaku AFC-7R
diffractometer
2080 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 2.8°
ω/2θ scansh = 1819
Absorption correction: ψ scan
(TEXSAN for Windows; Molecular Structure Corporation, 1999)
k = 016
Tmin = 0.949, Tmax = 0.974l = 83
3307 measured reflections3 standard reflections every 150 min
2872 independent reflections intensity decay: 1.2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 0.86 w = 1/[σ2(Fo2) + (0.1P)2 + 5.5554P]
where P = (Fo2 + 2Fc2)/3
2872 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
CH6N3+·C8H4NO6·H2OV = 1252.5 (4) Å3
Mr = 288.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.758 (3) ŵ = 0.13 mm1
b = 12.5955 (19) ÅT = 297 K
c = 6.8423 (12) Å0.40 × 0.35 × 0.20 mm
β = 100.006 (16)°
Data collection top
Rigaku AFC-7R
diffractometer
2080 reflections with I > 2σ(I)
Absorption correction: ψ scan
(TEXSAN for Windows; Molecular Structure Corporation, 1999)
Rint = 0.028
Tmin = 0.949, Tmax = 0.9743 standard reflections every 150 min
3307 measured reflections intensity decay: 1.2%
2872 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 0.86Δρmax = 0.33 e Å3
2872 reflectionsΔρmin = 0.40 e Å3
217 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O11A0.33502 (12)1.28306 (13)0.6829 (3)0.0402 (6)
O11B0.21101 (11)1.19235 (14)0.5452 (3)0.0436 (6)
O21A0.16688 (11)0.96584 (13)0.4120 (2)0.0331 (5)
O21B0.16155 (10)0.98708 (14)0.7330 (2)0.0339 (5)
O31A0.25485 (12)0.78120 (15)0.6336 (3)0.0480 (6)
O31B0.38515 (13)0.73913 (16)0.5523 (3)0.0551 (7)
N310.33335 (13)0.80279 (15)0.6115 (3)0.0338 (6)
C10.34791 (14)1.09732 (17)0.6688 (3)0.0266 (6)
C20.30745 (13)0.99645 (16)0.6370 (3)0.0240 (5)
C30.36807 (14)0.91080 (17)0.6560 (3)0.0270 (6)
C40.46275 (15)0.92106 (19)0.7140 (4)0.0337 (7)
C50.50006 (15)1.0204 (2)0.7553 (4)0.0374 (7)
C60.44276 (15)1.10785 (19)0.7288 (4)0.0346 (7)
C110.29065 (15)1.19500 (17)0.6278 (3)0.0283 (6)
C210.20296 (13)0.98198 (16)0.5881 (3)0.0250 (6)
N120.08940 (15)0.7473 (2)0.8170 (3)0.0406 (7)
N220.05841 (16)0.6993 (2)0.6799 (4)0.0454 (7)
N320.01159 (16)0.87191 (19)0.6668 (4)0.0409 (7)
C120.00621 (15)0.77276 (19)0.7218 (3)0.0313 (6)
O1W0.25121 (17)1.04247 (17)1.1102 (4)0.0536 (7)
H40.501300.860200.725100.0400*
H50.564201.028700.801200.0450*
H60.468501.176800.751900.0420*
H11A0.299 (3)1.340 (3)0.655 (5)0.069 (11)*
H12A0.104 (2)0.678 (3)0.838 (5)0.055 (9)*
H12B0.130 (2)0.796 (3)0.839 (5)0.056 (10)*
H22A0.113 (3)0.720 (3)0.605 (6)0.071 (11)*
H22B0.050 (2)0.637 (3)0.733 (5)0.056 (9)*
H32A0.030 (2)0.917 (3)0.683 (5)0.058 (10)*
H32B0.066 (3)0.894 (3)0.629 (5)0.063 (10)*
H1W0.222 (3)1.022 (3)0.994 (7)0.071 (12)*
H2W0.221 (3)1.018 (3)1.196 (7)0.078 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O11A0.0312 (9)0.0252 (8)0.0599 (12)0.0003 (7)0.0037 (8)0.0040 (8)
O11B0.0257 (8)0.0321 (9)0.0679 (12)0.0020 (7)0.0064 (8)0.0011 (8)
O21A0.0271 (8)0.0384 (9)0.0304 (8)0.0047 (7)0.0042 (6)0.0010 (7)
O21B0.0254 (8)0.0420 (9)0.0352 (9)0.0050 (7)0.0077 (6)0.0025 (7)
O31A0.0332 (9)0.0341 (9)0.0750 (14)0.0063 (7)0.0045 (9)0.0017 (9)
O31B0.0406 (10)0.0408 (10)0.0789 (15)0.0122 (8)0.0036 (10)0.0200 (10)
N310.0288 (9)0.0273 (9)0.0407 (11)0.0034 (8)0.0069 (8)0.0018 (8)
C10.0206 (9)0.0274 (10)0.0309 (11)0.0001 (8)0.0019 (8)0.0003 (8)
C20.0200 (9)0.0279 (10)0.0232 (9)0.0004 (7)0.0015 (7)0.0008 (8)
C30.0232 (10)0.0267 (10)0.0294 (10)0.0007 (8)0.0004 (8)0.0009 (8)
C40.0218 (10)0.0343 (12)0.0427 (13)0.0058 (9)0.0008 (9)0.0025 (10)
C50.0187 (9)0.0401 (13)0.0510 (14)0.0000 (9)0.0008 (9)0.0020 (11)
C60.0246 (10)0.0307 (11)0.0462 (13)0.0047 (9)0.0004 (9)0.0000 (10)
C110.0269 (10)0.0262 (10)0.0316 (11)0.0008 (8)0.0045 (8)0.0002 (8)
C210.0200 (9)0.0217 (9)0.0321 (11)0.0003 (7)0.0011 (8)0.0004 (8)
N120.0273 (10)0.0456 (13)0.0464 (12)0.0044 (10)0.0008 (9)0.0084 (10)
N220.0350 (11)0.0429 (13)0.0551 (14)0.0070 (10)0.0011 (10)0.0137 (11)
N320.0274 (10)0.0376 (12)0.0559 (14)0.0050 (9)0.0026 (9)0.0080 (10)
C120.0251 (10)0.0376 (12)0.0312 (11)0.0023 (9)0.0047 (8)0.0055 (9)
O1W0.0732 (15)0.0483 (12)0.0396 (11)0.0297 (11)0.0107 (11)0.0049 (9)
Geometric parameters (Å, º) top
O11A—C111.310 (3)N22—H22B0.87 (4)
O11B—C111.213 (3)N22—H22A0.91 (4)
O21A—C211.247 (2)N32—H32B0.85 (4)
O21B—C211.253 (2)N32—H32A0.83 (3)
O31A—N311.225 (3)C1—C61.395 (3)
O31B—N311.224 (3)C1—C111.491 (3)
O11A—H11A0.89 (4)C1—C21.405 (3)
O1W—H1W0.88 (5)C2—C31.393 (3)
O1W—H2W0.85 (5)C2—C211.531 (3)
N31—C31.467 (3)C3—C41.391 (3)
N12—C121.325 (3)C4—C51.376 (3)
N22—C121.324 (3)C5—C61.381 (3)
N32—C121.318 (3)C4—H40.9500
N12—H12B0.85 (4)C5—H50.9500
N12—H12A0.91 (4)C6—H60.9500
C11—O11A—H11A112 (3)N31—C3—C4116.29 (19)
H1W—O1W—H2W107 (4)N31—C3—C2120.22 (18)
O31A—N31—C3118.95 (19)C3—C4—C5119.3 (2)
O31A—N31—O31B123.6 (2)C4—C5—C6119.0 (2)
O31B—N31—C3117.41 (19)C1—C6—C5121.5 (2)
C12—N12—H12B118 (2)O11A—C11—O11B123.6 (2)
C12—N12—H12A119 (2)O11A—C11—C1113.95 (19)
H12A—N12—H12B122 (3)O11B—C11—C1122.4 (2)
H22A—N22—H22B123 (3)O21A—C21—C2118.40 (18)
C12—N22—H22A117 (2)O21B—C21—C2115.60 (17)
C12—N22—H22B120 (2)O21A—C21—O21B126.01 (19)
H32A—N32—H32B117 (3)C3—C4—H4120.00
C12—N32—H32B122 (3)C5—C4—H4120.00
C12—N32—H32A120 (2)C6—C5—H5121.00
C2—C1—C6120.6 (2)C4—C5—H5121.00
C6—C1—C11118.9 (2)C5—C6—H6119.00
C2—C1—C11120.35 (19)C1—C6—H6119.00
C3—C2—C21122.30 (18)N12—C12—N22120.6 (2)
C1—C2—C3115.93 (18)N12—C12—N32119.4 (2)
C1—C2—C21121.77 (18)N22—C12—N32120.0 (2)
C2—C3—C4123.5 (2)
O31A—N31—C3—C228.2 (3)C6—C1—C11—O11B167.8 (2)
O31A—N31—C3—C4152.5 (2)C1—C2—C3—N31175.49 (18)
O31B—N31—C3—C2151.2 (2)C1—C2—C3—C43.7 (3)
O31B—N31—C3—C428.0 (3)C21—C2—C3—N315.6 (3)
C6—C1—C2—C34.2 (3)C21—C2—C3—C4175.3 (2)
C6—C1—C2—C21174.8 (2)C1—C2—C21—O21A101.2 (2)
C11—C1—C2—C3172.36 (18)C1—C2—C21—O21B79.2 (3)
C11—C1—C2—C218.7 (3)C3—C2—C21—O21A79.9 (3)
C2—C1—C6—C51.2 (4)C3—C2—C21—O21B99.7 (2)
C11—C1—C6—C5175.4 (2)N31—C3—C4—C5179.1 (2)
C2—C1—C11—O11A173.34 (19)C2—C3—C4—C50.1 (4)
C2—C1—C11—O11B8.8 (3)C3—C4—C5—C63.1 (4)
C6—C1—C11—O11A10.1 (3)C4—C5—C6—C12.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O21B0.88 (5)1.90 (5)2.777 (3)176 (3)
O1W—H2W···O21Ai0.85 (5)1.91 (5)2.764 (3)173 (4)
O11A—H11A···O1Wii0.89 (4)1.65 (4)2.528 (3)169 (4)
N12—H12A···O21Aiii0.91 (4)2.06 (4)2.946 (3)167 (3)
N12—H12B···O21B0.85 (4)2.58 (4)3.286 (3)141 (3)
N12—H12B···O31A0.85 (4)2.51 (3)2.964 (3)114 (3)
N22—H22A···O11Biv0.91 (4)1.96 (4)2.846 (3)162 (3)
N22—H22B···O21Bv0.87 (4)2.54 (3)3.183 (3)132 (3)
N32—H32A···O21B0.83 (3)2.11 (3)2.905 (3)162 (3)
N32—H32B···O11Biv0.85 (4)2.51 (4)3.152 (3)134 (3)
N32—H32B···O21Aiv0.85 (4)2.30 (4)3.048 (3)148 (3)
C4—H4···O11Avi0.95002.58003.420 (3)148.00
C6—H6···O11A0.95002.36002.706 (3)101.00
C6—H6···O31Bvii0.95002.46003.179 (3)132.00
Symmetry codes: (i) x, y, z+1; (ii) x, y+5/2, z1/2; (iii) x, y+3/2, z+1/2; (iv) x, y+2, z+1; (v) x, y1/2, z+3/2; (vi) x+1, y1/2, z+3/2; (vii) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaCH6N3+·C8H4NO6·H2O
Mr288.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)297
a, b, c (Å)14.758 (3), 12.5955 (19), 6.8423 (12)
β (°) 100.006 (16)
V3)1252.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.40 × 0.35 × 0.20
Data collection
DiffractometerRigaku AFC-7R
Absorption correctionψ scan
(TEXSAN for Windows; Molecular Structure Corporation, 1999)
Tmin, Tmax0.949, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
3307, 2872, 2080
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.147, 0.86
No. of reflections2872
No. of parameters217
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.40

Computer programs: MSC/AFC Diffractmeter Control Software (Molecular Structure Corporation, 1999), MSC/AFC Diffractmeter Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1999), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O21B0.88 (5)1.90 (5)2.777 (3)176 (3)
O1W—H2W···O21Ai0.85 (5)1.91 (5)2.764 (3)173 (4)
O11A—H11A···O1Wii0.89 (4)1.65 (4)2.528 (3)169 (4)
N12—H12A···O21Aiii0.91 (4)2.06 (4)2.946 (3)167 (3)
N12—H12B···O21B0.85 (4)2.58 (4)3.286 (3)141 (3)
N12—H12B···O31A0.85 (4)2.51 (3)2.964 (3)114 (3)
N22—H22A···O11Biv0.91 (4)1.96 (4)2.846 (3)162 (3)
N22—H22B···O21Bv0.87 (4)2.54 (3)3.183 (3)132 (3)
N32—H32A···O21B0.83 (3)2.11 (3)2.905 (3)162 (3)
N32—H32B···O11Biv0.85 (4)2.51 (4)3.152 (3)134 (3)
N32—H32B···O21Aiv0.85 (4)2.30 (4)3.048 (3)148 (3)
Symmetry codes: (i) x, y, z+1; (ii) x, y+5/2, z1/2; (iii) x, y+3/2, z+1/2; (iv) x, y+2, z+1; (v) x, y1/2, z+3/2.
 

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