l-Histidinium dipicrate dihydrate.

In the title mol-ecular salt, C6H11N3O2 (2+)·2C6H2N3O7 (-)·2H2O, the histidine mol-ecule exists as a histidinium dication, being protonated at the N atom of the imidazole ring. The charges are balanced by two picrate anions and the compound crystallizes as a dihydrate. In the crystal, the components are linked via N-H⋯O and O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions, forming a three-dimensional supermolecular structure.

Related literature

For the role of pan class="Chemical">hydrogenn> bonding in the construction of supra­molecular structures, see: Braga et al. (2004 ▶); Harrowfield et al. (1995 ▶). For pan class="Chemical">picrates of biologically important mol­ecules, see: Harrison et al. (2007 ▶); Swamy et al. (2007 ▶); Bibal et al. (2003 ▶); Olsher et al. (1996 ▶). For bond angles in related structures, see: Yang et al. (2001 ▶).

Experimental

Crystal data

C6pan class="Species">H11N3n>O2 2+·2C6pan class="Species">H2N3O7 −·2H2O

M = 649.42

Monoclinic,

a = 6.6060 (4) Å

b = 25.7003 (13) Å

c = 7.9627 (5) Å

β = 107.532 (7)°

V = 1289.08 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker Kapn class="Chemical">pa Apan class="Chemical">PEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.970, T max = 0.985

5817 measured reflections

2982 independent reflections

2560 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.088

S = 1.09

2982 reflections

439 parameters

7 restraints

pan class="Disease">H atomsn> treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.18 e Å−3

Data collection: An class="Chemical">Pn>EX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813013949/su2602sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813013949/su2602Isup2.hkl

Click here for additional data file.

Supn class="Chemical">plementary material file. DOI: 10.1107/S1600536813013949/su2602Isup3.cml

Additional supn class="Chemical">plementary materials: crystallographic information; 3D view; checkCIF report

C6H11N3O22+·2C6H2N3O7−·2H2O	F(000) = 668
Mr = 649.42	Dx = 1.673 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5817 reflections
a = 6.6060 (4) Å	θ = 2.4–31.1°
b = 25.7003 (13) Å	µ = 0.15 mm−1
c = 7.9627 (5) Å	T = 293 K
β = 107.532 (7)°	Square, yellow
V = 1289.08 (13) Å3	0.20 × 0.15 × 0.10 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	2982 independent reflections
Radiation source: fine-focus sealed tube	2560 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω and φ scans	θmax = 28.9°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −8→8
Tmin = 0.970, Tmax = 0.985	k = −26→34
5817 measured reflections	l = −10→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088	w = 1/[σ2(Fo2) + (0.0341P)2 + 0.2411P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2982 reflections	Δρmax = 0.21 e Å−3
439 parameters	Δρmin = −0.18 e Å−3
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0095 (12)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

	x	y	z	Uiso*/Ueq
O1	1.1170 (5)	−0.00275 (12)	1.2736 (5)	0.0774 (11)
O2	0.8469 (5)	−0.04330 (11)	1.3342 (4)	0.0566 (8)
H2	0.9346	−0.0664	1.3719	0.085*
O3	0.9237 (4)	0.37442 (9)	0.5194 (3)	0.0366 (6)
O4	1.1711 (5)	0.33930 (12)	1.0182 (3)	0.0618 (9)
O5	0.9113 (6)	0.38681 (13)	0.8677 (4)	0.0659 (9)
O6	1.0105 (5)	0.15561 (11)	0.8787 (3)	0.0527 (7)
O7	0.9511 (5)	0.13208 (10)	0.6075 (3)	0.0507 (7)
O8	0.9119 (4)	0.26246 (10)	0.1693 (3)	0.0456 (6)
O9	0.7415 (5)	0.33288 (10)	0.1914 (3)	0.0489 (7)
O10	0.5060 (4)	0.11319 (9)	0.8159 (3)	0.0379 (6)
O11	0.4555 (4)	0.23048 (10)	1.1305 (3)	0.0443 (6)
O12	0.6326 (5)	0.16004 (10)	1.1346 (3)	0.0505 (7)
O13	0.4413 (5)	0.35254 (9)	0.6731 (4)	0.0529 (7)
O14	0.3963 (5)	0.32377 (10)	0.4098 (3)	0.0522 (7)
O15	0.2242 (5)	0.14022 (12)	0.3056 (3)	0.0565 (8)
O16	0.4623 (6)	0.09005 (11)	0.4743 (4)	0.0668 (9)
N1	0.8717 (5)	0.07237 (10)	1.0875 (4)	0.0354 (6)
H1A	0.7843	0.0987	1.0431	0.053*
H1B	0.8912	0.0535	1.0000	0.053*
H1C	0.9959	0.0848	1.1535	0.053*
N2	0.4952 (5)	0.00857 (12)	0.7727 (4)	0.0380 (7)
N3	0.4987 (6)	−0.07402 (13)	0.7471 (5)	0.0590 (10)
H3	0.4956	−0.1045	0.7020	0.071*
N4	1.0229 (5)	0.34810 (12)	0.8865 (4)	0.0388 (7)
N5	0.9722 (4)	0.16635 (11)	0.7214 (4)	0.0353 (7)
N6	0.8457 (5)	0.29442 (11)	0.2552 (3)	0.0322 (6)
N7	0.5317 (4)	0.19734 (11)	1.0568 (3)	0.0312 (6)
N8	0.4235 (4)	0.31696 (11)	0.5679 (4)	0.0315 (6)
N9	0.3649 (5)	0.13122 (11)	0.4434 (3)	0.0364 (7)
C1	0.9350 (6)	−0.00520 (14)	1.2718 (5)	0.0423 (9)
C2	0.7771 (6)	0.03902 (13)	1.1981 (4)	0.0344 (7)
C3	0.5503 (5)	0.02145 (14)	1.0983 (4)	0.0365 (8)
H3A	0.4943	0.0022	1.1793	0.044*
H3B	0.4629	0.0522	1.0624	0.044*
C4	0.5280 (5)	−0.01146 (13)	0.9395 (4)	0.0331 (7)
C5	0.4757 (6)	−0.03046 (16)	0.6596 (5)	0.0493 (10)
C6	0.5283 (7)	−0.06396 (16)	0.9212 (5)	0.0504 (10)
C7	0.9258 (5)	0.32737 (12)	0.5650 (4)	0.0256 (6)
C8	0.9775 (5)	0.30948 (13)	0.7450 (4)	0.0283 (7)
C9	0.9939 (5)	0.25863 (13)	0.7963 (4)	0.0275 (7)
H9	1.0308	0.2500	0.9151	0.033*
C10	0.9549 (5)	0.22013 (12)	0.6693 (4)	0.0265 (6)
C11	0.9070 (4)	0.23282 (12)	0.4924 (4)	0.0259 (6)
H11	0.8856	0.2068	0.4077	0.031*
C12	0.8915 (5)	0.28421 (11)	0.4435 (4)	0.0235 (6)
C13	0.4825 (5)	0.15872 (12)	0.7585 (4)	0.0260 (6)
C14	0.5012 (5)	0.20440 (12)	0.8692 (4)	0.0232 (6)
C15	0.4816 (5)	0.25485 (12)	0.8099 (4)	0.0246 (6)
H15	0.4977	0.2825	0.8884	0.030*
C16	0.4375 (5)	0.26384 (12)	0.6310 (4)	0.0237 (6)
C17	0.3974 (4)	0.22294 (12)	0.5116 (4)	0.0247 (6)
H17	0.3562	0.2293	0.3910	0.030*
C18	0.4195 (5)	0.17329 (12)	0.5740 (4)	0.0249 (6)
O17W	1.0107 (7)	0.43238 (13)	0.2418 (5)	0.0724 (10)
O18W	1.0051 (8)	0.03423 (14)	0.8230 (5)	0.0779 (11)
H17A	1.006 (14)	0.415 (3)	0.150 (7)	0.18 (4)*
H17B	1.04 (2)	0.411 (3)	0.325 (9)	0.31 (7)*
H18A	1.001 (9)	0.0022 (8)	0.808 (7)	0.086 (19)*
H18B	0.977 (15)	0.049 (2)	0.726 (5)	0.19 (4)*
H2A	0.763 (6)	0.0623 (16)	1.296 (5)	0.039 (10)*
H6	0.539 (7)	−0.0916 (19)	0.999 (6)	0.064 (13)*
H5	0.455 (7)	−0.029 (2)	0.536 (6)	0.068 (13)*
H2B	0.479 (7)	0.0432 (19)	0.751 (5)	0.053 (12)*

	U11	U22	U33	U12	U13	U23
O1	0.0441 (17)	0.047 (2)	0.123 (3)	0.0016 (14)	−0.0029 (17)	0.0338 (19)
O2	0.0723 (19)	0.0389 (16)	0.0567 (16)	0.0113 (15)	0.0166 (14)	0.0245 (13)
O3	0.0544 (15)	0.0211 (12)	0.0300 (11)	−0.0025 (11)	0.0064 (10)	−0.0010 (9)
O4	0.083 (2)	0.0564 (19)	0.0295 (13)	−0.0121 (17)	−0.0084 (13)	−0.0061 (13)
O5	0.096 (2)	0.0489 (19)	0.0517 (16)	0.0160 (18)	0.0213 (15)	−0.0173 (14)
O6	0.0750 (19)	0.0426 (16)	0.0386 (14)	−0.0024 (14)	0.0143 (13)	0.0187 (12)
O7	0.0717 (19)	0.0268 (14)	0.0524 (16)	−0.0034 (14)	0.0168 (13)	0.0001 (13)
O8	0.0684 (17)	0.0436 (16)	0.0298 (12)	−0.0007 (14)	0.0225 (12)	−0.0067 (11)
O9	0.0775 (19)	0.0295 (13)	0.0292 (12)	0.0062 (13)	0.0000 (12)	0.0058 (10)
O10	0.0591 (16)	0.0204 (12)	0.0299 (12)	0.0018 (11)	0.0070 (11)	0.0016 (9)
O11	0.0660 (16)	0.0427 (15)	0.0298 (12)	0.0072 (13)	0.0229 (12)	−0.0033 (11)
O12	0.080 (2)	0.0350 (14)	0.0269 (12)	0.0154 (14)	0.0007 (12)	0.0059 (11)
O13	0.079 (2)	0.0174 (13)	0.0575 (16)	0.0002 (13)	0.0135 (14)	−0.0002 (12)
O14	0.081 (2)	0.0376 (15)	0.0368 (13)	0.0005 (15)	0.0155 (13)	0.0172 (12)
O15	0.0706 (19)	0.0514 (18)	0.0320 (13)	−0.0160 (15)	−0.0078 (12)	−0.0063 (12)
O16	0.112 (3)	0.0364 (17)	0.0446 (16)	0.0147 (18)	0.0118 (17)	−0.0133 (13)
N1	0.0395 (15)	0.0194 (14)	0.0404 (16)	−0.0002 (12)	0.0017 (12)	0.0029 (11)
N2	0.0445 (17)	0.0244 (15)	0.0380 (16)	−0.0015 (14)	0.0019 (13)	−0.0004 (13)
N3	0.082 (3)	0.0247 (17)	0.058 (2)	−0.0058 (18)	0.0021 (18)	−0.0120 (15)
N4	0.0573 (19)	0.0330 (18)	0.0281 (14)	−0.0092 (15)	0.0158 (13)	−0.0041 (12)
N5	0.0356 (15)	0.0281 (16)	0.0416 (16)	−0.0027 (13)	0.0110 (12)	0.0070 (13)
N6	0.0444 (16)	0.0279 (15)	0.0219 (13)	−0.0078 (13)	0.0066 (11)	−0.0031 (11)
N7	0.0428 (16)	0.0261 (15)	0.0220 (13)	−0.0012 (13)	0.0056 (11)	−0.0016 (11)
N8	0.0286 (14)	0.0255 (15)	0.0399 (15)	−0.0017 (12)	0.0096 (11)	0.0060 (12)
N9	0.0547 (18)	0.0253 (15)	0.0290 (14)	−0.0073 (14)	0.0122 (13)	−0.0055 (12)
C1	0.048 (2)	0.0270 (19)	0.0382 (19)	−0.0013 (17)	−0.0072 (16)	0.0034 (15)
C2	0.0470 (19)	0.0246 (17)	0.0274 (15)	0.0004 (15)	0.0048 (14)	0.0022 (13)
C3	0.0412 (18)	0.0329 (18)	0.0341 (17)	0.0030 (16)	0.0097 (14)	0.0045 (14)
C4	0.0338 (16)	0.0230 (16)	0.0377 (17)	−0.0032 (14)	0.0037 (13)	0.0027 (14)
C5	0.058 (2)	0.038 (2)	0.043 (2)	−0.0062 (19)	0.0018 (18)	−0.0087 (18)
C6	0.064 (3)	0.031 (2)	0.045 (2)	−0.0083 (19)	0.0001 (19)	0.0019 (18)
C7	0.0269 (15)	0.0258 (16)	0.0221 (14)	−0.0025 (13)	0.0046 (11)	−0.0039 (12)
C8	0.0311 (16)	0.0290 (17)	0.0248 (15)	−0.0051 (14)	0.0081 (12)	−0.0064 (13)
C9	0.0295 (15)	0.0314 (18)	0.0224 (14)	−0.0003 (14)	0.0090 (12)	0.0034 (13)
C10	0.0251 (14)	0.0234 (16)	0.0313 (15)	−0.0005 (13)	0.0088 (11)	0.0038 (12)
C11	0.0254 (14)	0.0262 (16)	0.0263 (14)	−0.0033 (13)	0.0082 (11)	−0.0041 (12)
C12	0.0288 (15)	0.0187 (14)	0.0213 (14)	−0.0009 (12)	0.0051 (11)	−0.0007 (11)
C13	0.0275 (15)	0.0248 (16)	0.0251 (15)	0.0014 (13)	0.0070 (12)	−0.0005 (13)
C14	0.0267 (14)	0.0246 (16)	0.0176 (14)	0.0022 (13)	0.0057 (11)	0.0006 (11)
C15	0.0256 (14)	0.0233 (15)	0.0239 (14)	0.0018 (13)	0.0057 (11)	−0.0023 (12)
C16	0.0229 (14)	0.0202 (15)	0.0276 (15)	0.0015 (12)	0.0072 (11)	0.0048 (12)
C17	0.0254 (14)	0.0274 (17)	0.0215 (14)	−0.0005 (13)	0.0074 (11)	0.0027 (12)
C18	0.0270 (15)	0.0252 (16)	0.0215 (15)	−0.0004 (13)	0.0058 (12)	−0.0030 (11)
O17W	0.126 (3)	0.0397 (18)	0.0615 (19)	−0.0171 (19)	0.043 (2)	−0.0111 (15)
O18W	0.125 (3)	0.043 (2)	0.085 (3)	0.009 (2)	0.060 (2)	0.0001 (18)

O1—C1	1.199 (5)	N8—C16	1.448 (4)
O2—C1	1.311 (5)	N9—C18	1.468 (4)
O2—H2	0.8200	C1—C2	1.534 (5)
O3—C7	1.261 (4)	C2—C3	1.537 (5)
O4—N4	1.220 (4)	C2—H2A	1.01 (4)
O5—N4	1.220 (4)	C3—C4	1.491 (5)
O6—N5	1.232 (4)	C3—H3A	0.9700
O7—N5	1.242 (4)	C3—H3B	0.9700
O8—N6	1.230 (4)	C4—C6	1.357 (5)
O9—N6	1.224 (4)	C5—H5	0.96 (5)
O10—C13	1.249 (4)	C6—H6	0.93 (5)
O11—N7	1.225 (3)	C7—C12	1.444 (4)
O12—N7	1.224 (4)	C7—C8	1.445 (4)
O13—N8	1.222 (4)	C8—C9	1.363 (5)
O14—N8	1.230 (4)	C9—C10	1.383 (4)
O15—N9	1.228 (4)	C9—H9	0.9300
O16—N9	1.224 (4)	C10—C11	1.387 (4)
N1—C2	1.494 (4)	C11—C12	1.372 (4)
N1—H1A	0.8900	C11—H11	0.9300
N1—H1B	0.8900	C13—C14	1.451 (4)
N1—H1C	0.8900	C13—C18	1.450 (4)
N2—C5	1.328 (5)	C14—C15	1.373 (4)
N2—C4	1.380 (4)	C15—C16	1.385 (4)
N2—H2B	0.91 (5)	C15—H15	0.9300
N3—C5	1.303 (5)	C16—C17	1.388 (4)
N3—C6	1.365 (5)	C17—C18	1.361 (4)
N3—H3	0.8600	C17—H17	0.9300
N4—C8	1.463 (4)	O17W—H17A	0.84 (2)
N5—C10	1.438 (4)	O17W—H17B	0.84 (2)
N6—C12	1.461 (4)	O18W—H18A	0.83 (2)
N7—C14	1.457 (4)	O18W—H18B	0.83 (2)
C1—O2—H2	109.5	C6—C4—N2	105.8 (3)
C2—N1—H1A	109.5	C6—C4—C3	130.7 (3)
C2—N1—H1B	109.5	N2—C4—C3	123.5 (3)
H1A—N1—H1B	109.5	N3—C5—N2	108.3 (4)
C2—N1—H1C	109.5	N3—C5—H5	124 (3)
H1A—N1—H1C	109.5	N2—C5—H5	128 (3)
H1B—N1—H1C	109.5	C4—C6—N3	107.0 (4)
C5—N2—C4	109.0 (3)	C4—C6—H6	134 (3)
C5—N2—H2B	129 (3)	N3—C6—H6	119 (3)
C4—N2—H2B	121 (3)	O3—C7—C12	123.9 (3)
C5—N3—C6	109.8 (3)	O3—C7—C8	124.7 (3)
C5—N3—H3	125.1	C12—C7—C8	111.3 (3)
C6—N3—H3	125.1	C9—C8—C7	125.1 (3)
O5—N4—O4	123.7 (3)	C9—C8—N4	116.1 (3)
O5—N4—C8	118.8 (3)	C7—C8—N4	118.7 (3)
O4—N4—C8	117.5 (3)	C8—C9—C10	119.1 (3)
O6—N5—O7	121.8 (3)	C8—C9—H9	120.4
O7—N5—O7	0.0 (3)	C10—C9—H9	120.4
O6—N5—C10	118.9 (3)	C9—C10—C11	120.7 (3)
O7—N5—C10	119.3 (3)	C9—C10—N5	119.7 (3)
O9—N6—O8	123.9 (3)	C11—C10—N5	119.6 (3)
O9—N6—C12	119.2 (3)	C12—C11—C10	119.3 (3)
O8—N6—C12	116.9 (3)	C12—C11—H11	120.3
O12—N7—O11	122.8 (3)	C10—C11—H11	120.3
O12—N7—C14	120.2 (3)	C11—C12—C7	124.5 (3)
O11—N7—C14	117.0 (3)	C11—C12—N6	116.0 (3)
O13—N8—O14	123.4 (3)	C7—C12—N6	119.4 (3)
O13—N8—C16	119.0 (3)	O10—C13—C14	123.9 (3)
O14—N8—C16	117.6 (3)	O10—C13—C18	125.4 (3)
O16—N9—O15	123.6 (3)	C14—C13—C18	110.6 (3)
O16—N9—C18	119.5 (3)	C15—C14—C13	125.0 (2)
O15—N9—C18	116.9 (3)	C15—C14—N7	116.1 (3)
O1—C1—O2	126.3 (4)	C13—C14—N7	118.8 (3)
O1—C1—C2	121.9 (3)	C14—C15—C16	118.7 (3)
O2—C1—C2	111.7 (3)	C14—C15—H15	120.6
N1—C2—C1	107.1 (3)	C16—C15—H15	120.6
N1—C2—C3	112.3 (3)	C15—C16—C17	121.1 (3)
C1—C2—C3	115.1 (3)	C15—C16—N8	119.1 (3)
N1—C2—H2A	105 (2)	C17—C16—N8	119.8 (3)
C1—C2—H2A	111 (2)	C18—C17—C16	118.8 (3)
C3—C2—H2A	106 (2)	C18—C17—H17	120.6
C4—C3—C2	115.9 (3)	C16—C17—H17	120.6
C4—C3—H3A	108.3	C17—C18—C13	125.4 (3)
C2—C3—H3A	108.3	C17—C18—N9	117.1 (2)
C4—C3—H3B	108.3	C13—C18—N9	117.5 (3)
C2—C3—H3B	108.3	H17A—O17W—H17B	106 (3)
H3A—C3—H3B	107.4	H18A—O18W—H18B	109 (3)
O1—C1—C2—N1	17.5 (5)	C8—C7—C12—C11	−0.3 (4)
O2—C1—C2—N1	−164.4 (3)	O3—C7—C12—N6	−1.7 (5)
O1—C1—C2—C3	143.1 (4)	C8—C7—C12—N6	−177.6 (3)
O2—C1—C2—C3	−38.8 (4)	O9—N6—C12—C11	148.0 (3)
N1—C2—C3—C4	62.2 (4)	O8—N6—C12—C11	−30.3 (4)
C1—C2—C3—C4	−60.7 (4)	O9—N6—C12—C7	−34.5 (4)
C5—N2—C4—C6	0.3 (4)	O8—N6—C12—C7	147.2 (3)
C5—N2—C4—C3	−178.1 (3)	O10—C13—C14—C15	178.2 (3)
C2—C3—C4—C6	92.6 (5)	C18—C13—C14—C15	−5.6 (4)
C2—C3—C4—N2	−89.5 (4)	O10—C13—C14—N7	−5.3 (5)
C6—N3—C5—N2	1.7 (5)	C18—C13—C14—N7	170.9 (2)
C4—N2—C5—N3	−1.2 (5)	O12—N7—C14—C15	−150.2 (3)
N2—C4—C6—N3	0.7 (4)	O11—N7—C14—C15	28.7 (4)
C3—C4—C6—N3	179.0 (4)	O12—N7—C14—C13	33.0 (4)
C5—N3—C6—C4	−1.5 (5)	O11—N7—C14—C13	−148.1 (3)
O3—C7—C8—C9	−175.4 (3)	C13—C14—C15—C16	1.0 (5)
C12—C7—C8—C9	0.4 (4)	N7—C14—C15—C16	−175.5 (2)
O3—C7—C8—N4	2.6 (5)	C14—C15—C16—C17	4.9 (4)
C12—C7—C8—N4	178.4 (3)	C14—C15—C16—N8	−178.0 (3)
O5—N4—C8—C9	−139.3 (3)	O13—N8—C16—C15	−3.4 (4)
O4—N4—C8—C9	40.2 (4)	O14—N8—C16—C15	175.9 (3)
O5—N4—C8—C7	42.6 (5)	O13—N8—C16—C17	173.8 (3)
O4—N4—C8—C7	−138.0 (3)	O14—N8—C16—C17	−6.9 (4)
C7—C8—C9—C10	−1.4 (5)	C15—C16—C17—C18	−5.4 (4)
N4—C8—C9—C10	−179.4 (3)	N8—C16—C17—C18	177.5 (3)
C8—C9—C10—C11	2.2 (4)	C16—C17—C18—C13	0.1 (5)
C8—C9—C10—N5	179.8 (3)	C16—C17—C18—N9	176.9 (3)
O6—N5—C10—C9	3.9 (4)	O10—C13—C18—C17	−178.8 (3)
O7—N5—C10—C9	−175.1 (3)	C14—C13—C18—C17	5.1 (4)
O6—N5—C10—C11	−178.5 (3)	O10—C13—C18—N9	4.4 (5)
O7—N5—C10—C11	2.5 (4)	C14—C13—C18—N9	−171.8 (3)
C9—C10—C11—C12	−2.2 (4)	O16—N9—C18—C17	147.2 (3)
N5—C10—C11—C12	−179.7 (3)	O15—N9—C18—C17	−31.3 (4)
C10—C11—C12—C7	1.2 (5)	O16—N9—C18—C13	−35.7 (4)
C10—C11—C12—N6	178.6 (2)	O15—N9—C18—C13	145.8 (3)
O3—C7—C12—C11	175.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O10	0.89	2.19	2.909 (3)	138
N1—H1A···O12	0.89	2.11	2.841 (4)	139
N1—H1B···O18W	0.89	1.85	2.700 (5)	158
N1—H1C···O15i	0.89	2.16	3.007 (4)	159
N2—H2B···O10	0.91 (5)	1.86 (5)	2.709 (4)	154 (4)
N2—H2B···O16	0.91 (5)	2.49 (4)	3.125 (4)	128 (3)
N3—H3···O9ii	0.86	2.56	2.992 (5)	112
N3—H3···O14ii	0.86	2.25	3.077 (4)	160
O2—H2···O3iii	0.82	1.86	2.657 (3)	165
O17W—H17A···O5iv	0.84 (2)	2.27 (3)	3.082 (4)	162 (9)
O17W—H17B···O3	0.84 (2)	2.14 (8)	2.864 (4)	144 (12)
O18W—H18A···O17Wv	0.83 (2)	1.83 (2)	2.664 (5)	176 (5)
O18W—H18B···O7	0.83 (2)	2.32 (4)	3.005 (5)	140 (6)
C3—H3B···O10	0.97	2.59	3.210 (4)	122
C9—H9···O8vi	0.93	2.40	3.177 (4)	141
C17—H17···O11iv	0.93	2.36	3.177 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O10	0.89	2.19	2.909 (3)	138
N1—H1A⋯O12	0.89	2.11	2.841 (4)	139
N1—H1B⋯O18W	0.89	1.85	2.700 (5)	158
N1—H1C⋯O15i	0.89	2.16	3.007 (4)	159
N2—H2B⋯O10	0.91 (5)	1.86 (5)	2.709 (4)	154 (4)
N2—H2B⋯O16	0.91 (5)	2.49 (4)	3.125 (4)	128 (3)
N3—H3⋯O9ii	0.86	2.56	2.992 (5)	112
N3—H3⋯O14ii	0.86	2.25	3.077 (4)	160
O2—H2⋯O3iii	0.82	1.86	2.657 (3)	165
O17W—H17A⋯O5iv	0.84 (2)	2.27 (3)	3.082 (4)	162 (9)
O17W—H17B⋯O3	0.84 (2)	2.14 (8)	2.864 (4)	144 (12)
O18W—H18A⋯O17W v	0.83 (2)	1.83 (2)	2.664 (5)	176 (5)
O18W—H18B⋯O7	0.83 (2)	2.32 (4)	3.005 (5)	140 (6)
C3—H3B⋯O10	0.97	2.59	3.210 (4)	122
C9—H9⋯O8vi	0.93	2.40	3.177 (4)	141
C17—H17⋯O11iv	0.93	2.36	3.177 (3)	147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .