Ethenzamide-gentisic acid-acetic acid (2/1/1).

In the title co-crystal solvate, 2-ethoxy-benzamide-2,5-dihydroxy-benzoic acid-ethanoic acid (2/1/1), 2C(9)H(11)NO(2)·C(7)H(6)O(4)·C(2)H(4)O(2), two nonsteroidal anti-inflammatory drugs, ethenzamide (systematic name: 2-ethoxy-benzamide) and gentisic acid (systematic name: 2,5-dihydroxy-benzoic acid), together with acetic acid (systematic name: ethanoic acid) form a four-component mol-ecular assembly held together by N-H⋯O and O-H⋯O hydrogen bonds. This assembly features two symmetry-independent mol-ecules of ethenzamide, forming supra-molecular acid-amide heterosynthons with gentisic acid and acetic acid. These heterosynthons involve quite strong O-H⋯O [O⋯O = 2.5446 (15) and 2.5327 (15) Å] and less strong N-H⋯O [N⋯O = 2.9550 (17) and 2.9542 (17) Å] hydrogen bonds. The overall crystal packing features several C-H⋯O and π-π stacking inter-actions [centroid-centroid distance = 3.7792 (11) Å].

Related literature

For information on three polymorphs of a 1:1 co-crystal involving ethenzamide and gentisic acid, see: Aitipamula et al. (2009a ▶). For other co-crystals of ethenzamide, see: Aitipamula et al. (2009b ▶); Moribe et al. (2004 ▶). For related information on the drug activity of ethenzamide, see: Hirasawa et al. (1999 ▶). For the crystal structure of ethenzamide, see: Pagola & Stephens (2009 ▶). For related information on the drug activity of gentisic acid, see: Lorico et al. (1986 ▶). For more information on the supra­molecular heterosynthons, see: Fleischman et al. (2003 ▶). For reviews on pharmaceutical co-crystals, see: Schultheiss & Newman (2009 ▶); Almarsson & Zaworotko (2004 ▶). For more information on the hydrogen bonding, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

2C9H11NO2·C7H6O4·C2H4O2

M = 544.55

Triclinic,

a = 8.8083 (18) Å

b = 8.8802 (18) Å

c = 19.880 (4) Å

α = 93.65 (3)°

β = 93.55 (3)°

γ = 119.45 (3)°

V = 1343.5 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 110 K

0.33 × 0.29 × 0.22 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.967, T max = 0.978

19296 measured reflections

6594 independent reflections

6074 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.135

S = 1.11

6594 reflections

380 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012407/fb2192sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012407/fb2192Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

2C9H11NO2·C7H6O4·C2H4O2	Z = 2
Mr = 544.55	F(000) = 576
Triclinic, P1	Dx = 1.346 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8083 (18) Å	Cell parameters from 3760 reflections
b = 8.8802 (18) Å	θ = 2.1–31.0°
c = 19.880 (4) Å	µ = 0.10 mm−1
α = 93.65 (3)°	T = 110 K
β = 93.55 (3)°	Block, yellow
γ = 119.45 (3)°	0.33 × 0.29 × 0.22 mm
V = 1343.5 (6) Å3

Rigaku Saturn CCD area-detector diffractometer	6594 independent reflections
Radiation source: fine-focus sealed tube	6074 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (Blessing, 1995)	h = −11→11
Tmin = 0.967, Tmax = 0.978	k = −11→9
19296 measured reflections	l = −26→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0677P)2 + 0.2882P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
6594 reflections	Δρmax = 0.25 e Å−3
380 parameters	Δρmin = −0.23 e Å−3
0 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: 0.0054 (18)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O4	0.18598 (11)	0.96579 (12)	0.43017 (5)	0.0280 (2)
O9	1.05478 (12)	0.54627 (13)	0.63748 (5)	0.0319 (2)
O3	−0.22283 (12)	0.57234 (13)	0.51754 (5)	0.0324 (2)
O10	0.76432 (12)	0.38996 (13)	0.61300 (5)	0.0316 (2)
H20	0.781 (2)	0.464 (3)	0.5756 (10)	0.047*
N2	0.06949 (14)	0.72419 (16)	0.51542 (6)	0.0281 (2)
H10	0.079 (2)	0.668 (2)	0.5509 (9)	0.034*
H7	0.159 (2)	0.811 (2)	0.5000 (9)	0.034*
C16	−0.09157 (16)	0.68847 (16)	0.49396 (6)	0.0249 (2)
C11	0.01615 (16)	0.92217 (16)	0.41021 (6)	0.0251 (3)
C12	−0.02542 (17)	1.00581 (18)	0.36157 (7)	0.0295 (3)
H12	0.0654	1.0958	0.3409	0.035*
C18	0.49661 (17)	1.13984 (19)	0.43493 (7)	0.0325 (3)
H18A	0.5037	1.1604	0.4843	0.049*
H18B	0.5932	1.2403	0.4180	0.049*
H18C	0.5050	1.0356	0.4229	0.049*
C17	0.32440 (16)	1.11405 (17)	0.40346 (7)	0.0285 (3)
H17A	0.3150	1.2191	0.4149	0.034*
H17B	0.3155	1.0925	0.3535	0.034*
C10	−0.11871 (16)	0.78677 (16)	0.44080 (6)	0.0246 (2)
C15	−0.29227 (16)	0.74279 (17)	0.42099 (7)	0.0277 (3)
H15	−0.3844	0.6526	0.4411	0.033*
C13	−0.19922 (18)	0.95831 (18)	0.34313 (7)	0.0308 (3)
H13	−0.2264	1.0162	0.3099	0.037*
C26	0.91047 (17)	0.43317 (17)	0.65051 (7)	0.0283 (3)
C14	−0.33339 (17)	0.82690 (18)	0.37295 (7)	0.0308 (3)
H14	−0.4521	0.7951	0.3605	0.037*
C27	0.8867 (2)	0.3342 (2)	0.71097 (8)	0.0371 (3)
H27A	0.9874	0.3168	0.7199	0.056*
H27B	0.7791	0.2209	0.7020	0.056*
H27C	0.8780	0.4001	0.7505	0.056*
O1	0.91975 (12)	0.71644 (12)	1.01611 (5)	0.0296 (2)
O2	0.45825 (12)	0.67508 (13)	0.93005 (5)	0.0298 (2)
C1	0.66698 (16)	0.57974 (16)	0.93614 (6)	0.0247 (2)
N1	0.75912 (17)	0.84922 (16)	1.00868 (6)	0.0322 (3)
H1	0.656 (2)	0.845 (2)	0.9926 (9)	0.039*
H2	0.829 (2)	0.926 (2)	1.0438 (9)	0.039*
C7	0.78960 (16)	0.72148 (16)	0.98983 (6)	0.0254 (2)
C2	0.50360 (17)	0.55485 (16)	0.90874 (6)	0.0262 (3)
C6	0.71780 (18)	0.46025 (17)	0.91414 (7)	0.0291 (3)
H6	0.8278	0.4760	0.9321	0.035*
C8	0.28786 (17)	0.65018 (19)	0.90704 (7)	0.0316 (3)
H8A	0.1940	0.5434	0.9228	0.038*
H8B	0.2710	0.6394	0.8569	0.038*
C9	0.2832 (2)	0.8079 (2)	0.93678 (8)	0.0388 (3)
H9A	0.3025	0.8181	0.9863	0.058*
H9B	0.1687	0.7961	0.9232	0.058*
H9C	0.3755	0.9123	0.9201	0.058*
C4	0.44999 (19)	0.29481 (18)	0.84136 (7)	0.0344 (3)
H4	0.3759	0.1974	0.8093	0.041*
C3	0.39524 (18)	0.41077 (18)	0.86209 (7)	0.0314 (3)
H3	0.2839	0.3921	0.8445	0.038*
C5	0.61151 (19)	0.31929 (18)	0.86680 (7)	0.0330 (3)
H5	0.6489	0.2402	0.8519	0.040*
O8	0.70122 (13)	0.23351 (13)	0.25999 (5)	0.0327 (2)
H19	0.784 (3)	0.317 (3)	0.2955 (10)	0.049*
O6	0.13707 (13)	−0.09895 (13)	0.11728 (5)	0.0319 (2)
H11	0.039 (3)	−0.166 (3)	0.0787 (10)	0.048*
O5	−0.01505 (12)	0.03810 (13)	0.13600 (5)	0.0327 (2)
O7	0.10781 (13)	0.29851 (13)	0.23160 (5)	0.0325 (2)
H16	0.033 (3)	0.217 (3)	0.1981 (10)	0.049*
C24	0.41450 (17)	0.13298 (16)	0.20904 (6)	0.0254 (2)
H24	0.4210	0.0417	0.1842	0.030*
C22	0.54594 (17)	0.38590 (17)	0.29022 (6)	0.0285 (3)
H22	0.6432	0.4691	0.3207	0.034*
C23	0.55542 (16)	0.25175 (17)	0.25389 (6)	0.0264 (3)
C19	0.26205 (16)	0.14500 (16)	0.19962 (6)	0.0248 (2)
C25	0.11617 (17)	0.02315 (16)	0.14875 (6)	0.0262 (3)
C21	0.39528 (17)	0.39826 (17)	0.28208 (7)	0.0285 (3)
H21	0.3894	0.4890	0.3076	0.034*
C20	0.25202 (17)	0.27906 (17)	0.23681 (6)	0.0263 (3)

	U11	U22	U33	U12	U13	U23
O4	0.0206 (4)	0.0310 (5)	0.0326 (5)	0.0122 (4)	0.0044 (3)	0.0081 (4)
O9	0.0255 (4)	0.0373 (5)	0.0296 (5)	0.0130 (4)	0.0020 (3)	0.0044 (4)
O3	0.0221 (4)	0.0334 (5)	0.0383 (5)	0.0106 (4)	0.0038 (4)	0.0089 (4)
O10	0.0241 (4)	0.0338 (5)	0.0340 (5)	0.0119 (4)	0.0045 (4)	0.0054 (4)
N2	0.0215 (5)	0.0322 (6)	0.0288 (5)	0.0116 (4)	0.0025 (4)	0.0071 (4)
C16	0.0222 (5)	0.0254 (6)	0.0258 (6)	0.0112 (5)	0.0028 (4)	−0.0010 (4)
C11	0.0230 (5)	0.0271 (6)	0.0257 (6)	0.0136 (5)	0.0007 (4)	−0.0018 (5)
C12	0.0292 (6)	0.0305 (6)	0.0301 (6)	0.0160 (5)	0.0026 (5)	0.0035 (5)
C18	0.0246 (6)	0.0338 (7)	0.0383 (7)	0.0130 (5)	0.0055 (5)	0.0097 (6)
C17	0.0243 (6)	0.0285 (6)	0.0314 (6)	0.0115 (5)	0.0059 (5)	0.0068 (5)
C10	0.0234 (6)	0.0246 (6)	0.0251 (6)	0.0121 (5)	0.0010 (4)	−0.0025 (4)
C15	0.0234 (6)	0.0258 (6)	0.0308 (6)	0.0111 (5)	−0.0010 (5)	−0.0037 (5)
C13	0.0327 (7)	0.0301 (7)	0.0317 (6)	0.0185 (5)	−0.0046 (5)	−0.0006 (5)
C26	0.0293 (6)	0.0302 (6)	0.0275 (6)	0.0166 (5)	0.0049 (5)	0.0002 (5)
C14	0.0254 (6)	0.0301 (7)	0.0359 (7)	0.0149 (5)	−0.0050 (5)	−0.0040 (5)
C27	0.0446 (8)	0.0372 (8)	0.0330 (7)	0.0220 (6)	0.0083 (6)	0.0079 (6)
O1	0.0282 (4)	0.0290 (5)	0.0326 (5)	0.0159 (4)	−0.0005 (4)	−0.0008 (4)
O2	0.0302 (5)	0.0331 (5)	0.0305 (5)	0.0195 (4)	0.0020 (4)	0.0017 (4)
C1	0.0276 (6)	0.0228 (6)	0.0231 (6)	0.0117 (5)	0.0045 (4)	0.0048 (4)
N1	0.0356 (6)	0.0299 (6)	0.0338 (6)	0.0201 (5)	−0.0035 (5)	−0.0042 (5)
C7	0.0280 (6)	0.0238 (6)	0.0253 (6)	0.0130 (5)	0.0050 (4)	0.0054 (4)
C2	0.0299 (6)	0.0275 (6)	0.0235 (6)	0.0154 (5)	0.0062 (5)	0.0060 (5)
C6	0.0309 (6)	0.0281 (6)	0.0306 (6)	0.0162 (5)	0.0053 (5)	0.0039 (5)
C8	0.0275 (6)	0.0372 (7)	0.0342 (7)	0.0186 (6)	0.0047 (5)	0.0091 (5)
C9	0.0370 (7)	0.0420 (8)	0.0474 (8)	0.0261 (7)	0.0089 (6)	0.0101 (6)
C4	0.0375 (7)	0.0292 (7)	0.0298 (7)	0.0123 (6)	0.0017 (5)	−0.0008 (5)
C3	0.0299 (6)	0.0316 (7)	0.0290 (6)	0.0126 (5)	0.0018 (5)	0.0025 (5)
C5	0.0391 (7)	0.0288 (7)	0.0332 (7)	0.0188 (6)	0.0052 (5)	−0.0001 (5)
O8	0.0291 (5)	0.0363 (5)	0.0357 (5)	0.0198 (4)	−0.0039 (4)	−0.0006 (4)
O6	0.0344 (5)	0.0295 (5)	0.0336 (5)	0.0193 (4)	−0.0058 (4)	−0.0050 (4)
O5	0.0278 (5)	0.0350 (5)	0.0357 (5)	0.0176 (4)	−0.0032 (4)	−0.0034 (4)
O7	0.0290 (5)	0.0329 (5)	0.0383 (5)	0.0185 (4)	0.0006 (4)	−0.0026 (4)
C24	0.0287 (6)	0.0240 (6)	0.0249 (6)	0.0141 (5)	0.0025 (4)	0.0037 (4)
C22	0.0297 (6)	0.0260 (6)	0.0257 (6)	0.0110 (5)	0.0007 (5)	0.0016 (5)
C23	0.0260 (6)	0.0278 (6)	0.0266 (6)	0.0142 (5)	0.0021 (4)	0.0054 (5)
C19	0.0255 (6)	0.0235 (6)	0.0243 (6)	0.0113 (5)	0.0019 (4)	0.0037 (4)
C25	0.0271 (6)	0.0255 (6)	0.0266 (6)	0.0135 (5)	0.0029 (4)	0.0040 (5)
C21	0.0314 (6)	0.0254 (6)	0.0287 (6)	0.0142 (5)	0.0034 (5)	0.0012 (5)
C20	0.0269 (6)	0.0264 (6)	0.0270 (6)	0.0138 (5)	0.0045 (4)	0.0051 (5)

O4—C11	1.3720 (15)	C1—C7	1.4965 (19)
O4—C17	1.4466 (16)	N1—C7	1.3256 (17)
O9—C26	1.2289 (17)	N1—H1	0.930 (19)
O3—C16	1.2555 (16)	N1—H2	0.90 (2)
O10—C26	1.3112 (17)	C2—C3	1.395 (2)
O10—H20	0.99 (2)	C6—C5	1.385 (2)
N2—C16	1.3269 (16)	C6—H6	0.9500
N2—H10	0.913 (18)	C8—C9	1.506 (2)
N2—H7	0.879 (18)	C8—H8A	0.9900
C16—C10	1.4924 (19)	C8—H8B	0.9900
C11—C12	1.3913 (19)	C9—H9A	0.9800
C11—C10	1.4159 (18)	C9—H9B	0.9800
C12—C13	1.3899 (18)	C9—H9C	0.9800
C12—H12	0.9500	C4—C5	1.386 (2)
C18—C17	1.5058 (18)	C4—C3	1.386 (2)
C18—H18A	0.9800	C4—H4	0.9500
C18—H18B	0.9800	C3—H3	0.9500
C18—H18C	0.9800	C5—H5	0.9500
C17—H17A	0.9900	O8—C23	1.3705 (16)
C17—H17B	0.9900	O8—H19	0.96 (2)
C10—C15	1.4012 (17)	O6—C25	1.3134 (16)
C15—C14	1.384 (2)	O6—H11	1.02 (2)
C15—H15	0.9500	O5—C25	1.2397 (16)
C13—C14	1.389 (2)	O7—C20	1.3622 (16)
C13—H13	0.9500	O7—H16	0.90 (2)
C26—C27	1.499 (2)	C24—C23	1.3798 (19)
C14—H14	0.9500	C24—C19	1.4007 (18)
C27—H27A	0.9800	C24—H24	0.9500
C27—H27B	0.9800	C22—C21	1.3849 (19)
C27—H27C	0.9800	C22—C23	1.3941 (19)
O1—C7	1.2523 (16)	C22—H22	0.9500
O2—C2	1.3644 (16)	C19—C20	1.4040 (18)
O2—C8	1.4444 (16)	C19—C25	1.4756 (19)
C1—C6	1.3963 (18)	C21—C20	1.3955 (19)
C1—C2	1.4112 (18)	C21—H21	0.9500
C11—O4—C17	117.67 (10)	O1—C7—N1	121.31 (12)
C26—O10—H20	113.5 (11)	O1—C7—C1	118.85 (12)
C16—N2—H10	116.3 (11)	N1—C7—C1	119.85 (12)
C16—N2—H7	119.0 (11)	O2—C2—C3	122.70 (12)
H10—N2—H7	123.8 (16)	O2—C2—C1	117.45 (11)
O3—C16—N2	121.07 (12)	C3—C2—C1	119.85 (12)
O3—C16—C10	119.00 (11)	C5—C6—C1	121.49 (13)
N2—C16—C10	119.93 (12)	C5—C6—H6	119.3
O4—C11—C12	122.18 (12)	C1—C6—H6	119.3
O4—C11—C10	117.69 (11)	O2—C8—C9	106.37 (12)
C12—C11—C10	120.13 (12)	O2—C8—H8A	110.5
C13—C12—C11	120.32 (13)	C9—C8—H8A	110.5
C13—C12—H12	119.8	O2—C8—H8B	110.5
C11—C12—H12	119.8	C9—C8—H8B	110.5
C17—C18—H18A	109.5	H8A—C8—H8B	108.6
C17—C18—H18B	109.5	C8—C9—H9A	109.5
H18A—C18—H18B	109.5	C8—C9—H9B	109.5
C17—C18—H18C	109.5	H9A—C9—H9B	109.5
H18A—C18—H18C	109.5	C8—C9—H9C	109.5
H18B—C18—H18C	109.5	H9A—C9—H9C	109.5
O4—C17—C18	107.57 (11)	H9B—C9—H9C	109.5
O4—C17—H17A	110.2	C5—C4—C3	120.78 (13)
C18—C17—H17A	110.2	C5—C4—H4	119.6
O4—C17—H17B	110.2	C3—C4—H4	119.6
C18—C17—H17B	110.2	C4—C3—C2	120.05 (13)
H17A—C17—H17B	108.5	C4—C3—H3	120.0
C15—C10—C11	117.89 (12)	C2—C3—H3	120.0
C15—C10—C16	116.73 (12)	C6—C5—C4	119.29 (13)
C11—C10—C16	125.37 (11)	C6—C5—H5	120.4
C14—C15—C10	121.93 (13)	C4—C5—H5	120.4
C14—C15—H15	119.0	C23—O8—H19	109.3 (12)
C10—C15—H15	119.0	C25—O6—H11	110.3 (11)
C14—C13—C12	120.47 (13)	C20—O7—H16	105.4 (13)
C14—C13—H13	119.8	C23—C24—C19	120.98 (12)
C12—C13—H13	119.8	C23—C24—H24	119.5
O9—C26—O10	122.84 (13)	C19—C24—H24	119.5
O9—C26—C27	122.78 (13)	C21—C22—C23	120.24 (12)
O10—C26—C27	114.38 (12)	C21—C22—H22	119.9
C15—C14—C13	119.25 (12)	C23—C22—H22	119.9
C15—C14—H14	120.4	O8—C23—C24	117.91 (12)
C13—C14—H14	120.4	O8—C23—C22	122.62 (12)
C26—C27—H27A	109.5	C24—C23—C22	119.46 (12)
C26—C27—H27B	109.5	C24—C19—C20	119.47 (12)
H27A—C27—H27B	109.5	C24—C19—C25	120.45 (12)
C26—C27—H27C	109.5	C20—C19—C25	120.02 (12)
H27A—C27—H27C	109.5	O5—C25—O6	122.74 (12)
H27B—C27—H27C	109.5	O5—C25—C19	121.85 (12)
C2—O2—C8	119.79 (11)	O6—C25—C19	115.40 (11)
C6—C1—C2	118.51 (12)	C22—C21—C20	120.82 (12)
C6—C1—C7	116.30 (12)	C22—C21—H21	119.6
C2—C1—C7	125.14 (12)	C20—C21—H21	119.6
C7—N1—H1	120.7 (11)	O7—C20—C21	117.69 (12)
C7—N1—H2	117.4 (12)	O7—C20—C19	123.28 (12)
H1—N1—H2	120.6 (16)	C21—C20—C19	119.02 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.926 (19)	1.941 (18)	2.6472 (19)	131.6 (14)
N1—H2···O5i	0.90 (2)	2.085 (18)	2.9550 (17)	163.0 (15)
N2—H7···O4	0.879 (18)	1.959 (17)	2.6536 (16)	135.0 (17)
N2—H10···O9ii	0.912 (18)	2.057 (17)	2.9542 (17)	167.4 (17)
O6—H11···O1iii	1.02 (2)	1.53 (2)	2.5327 (15)	167.0 (18)
O7—H16···O5	0.90 (2)	1.80 (2)	2.6183 (15)	149 (3)
O8—H19···O9iv	0.96 (2)	1.77 (2)	2.7231 (16)	173 (2)
O10—H20···O3v	0.99 (2)	1.56 (2)	2.5446 (15)	171 (2)
C8—H8A···O1vi	0.99	2.46	3.3768 (19)	154
C13—H13···O8vii	0.95	2.55	3.452 (2)	159
C14—H14···O10viii	0.95	2.53	3.348 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.926 (19)	1.941 (18)	2.6472 (19)	131.6 (14)
N1—H2⋯O5i	0.90 (2)	2.085 (18)	2.9550 (17)	163.0 (15)
N2—H7⋯O4	0.879 (18)	1.959 (17)	2.6536 (16)	135.0 (17)
N2—H10⋯O9ii	0.912 (18)	2.057 (17)	2.9542 (17)	167.4 (17)
O6—H11⋯O1iii	1.02 (2)	1.53 (2)	2.5327 (15)	167.0 (18)
O7—H16⋯O5	0.90 (2)	1.80 (2)	2.6183 (15)	149 (3)
O8—H19⋯O9iv	0.96 (2)	1.77 (2)	2.7231 (16)	173 (2)
O10—H20⋯O3v	0.99 (2)	1.56 (2)	2.5446 (15)	171 (2)
C8—H8A⋯O1vi	0.99	2.46	3.3768 (19)	154
C13—H13⋯O8vii	0.95	2.55	3.452 (2)	159
C14—H14⋯O10viii	0.95	2.53	3.348 (2)	145

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