Tetra-aqua-bis-[1-(3-carb-oxy-phen-yl)-4,4'-bipyridin-1-ium-κN]zinc bis-(4,5-carb-oxy-benzene-1,2-dicarboxyl-ate) 2.5-hydrate.

In the complex cation of the title compound, [Zn(C(17)H(13)N(2)O(2))(2)(H(2)O)(4)](C(10)H(4)O(8))(2)·2.5H(2)O, the Zn(II) atom, lying on an inversion center, is coordinated by two N atoms from two N-(3-carb-oxy-phen-yl)-4,4'-bipyridin-1-ium ligands and four water mol-ecules in a distorted octa-hedral geometry. The pyromellitate anion is double deprotonated. O-H⋯O and C-H⋯O hydrogen bonds connect the cations, anions and uncoordinated water mol-ecules into a three-dimensional supra-molecular network. One of the two lattice water molecules shows an occupancy of 0.25. An intra-molecular O-H⋯O hydrogen bond is present in the anion.

Related literature

For background to the structures and applications of viologen compounds, see: Ebbesen et al. (1984 ▶); Jin et al. (2010 ▶); Sun et al. (2005 ▶); Xu et al. (2007 ▶).

Experimental

Crystal data

[Zn(C17H13N2O2)2(H2O)4](C10H4O8)2·2.5H2O

M = 1241.33

Monoclinic,

a = 7.5476 (2) Å

b = 19.5528 (4) Å

c = 19.2752 (4) Å

β = 110.431 (2)°

V = 2665.63 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.56 mm−1

T = 298 K

0.43 × 0.41 × 0.37 mm

Data collection

Bruker APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.781, T max = 0.825

25451 measured reflections

4867 independent reflections

4250 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.078

S = 1.06

4867 reflections

429 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811045156/hy2468sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045156/hy2468Isup2.hkl

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

[Zn(C17H13N2O2)2(H2O)4](C10H4O8)2·2.5H2O	F(000) = 1282
Mr = 1241.33	Dx = 1.547 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4867 reflections
a = 7.5476 (2) Å	θ = 3.1–25.4°
b = 19.5528 (4) Å	µ = 0.56 mm−1
c = 19.2752 (4) Å	T = 298 K
β = 110.431 (2)°	Block, yellow
V = 2665.63 (10) Å3	0.43 × 0.41 × 0.37 mm
Z = 2

Bruker APEX CCD diffractometer	4867 independent reflections
Radiation source: fine-focus sealed tube	4250 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 25.4°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.781, Tmax = 0.825	k = −23→23
25451 measured reflections	l = −23→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0331P)2 + 1.443P] where P = (Fo2 + 2Fc2)/3
4867 reflections	(Δ/σ)max = 0.001
429 parameters	Δρmax = 0.29 e Å−3
4 restraints	Δρmin = −0.36 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.5000	0.5000	0.5000	0.02391 (9)
O1	0.5186 (2)	1.24085 (7)	0.33078 (8)	0.0434 (4)
H7	0.583 (4)	1.2716 (14)	0.3626 (15)	0.065*
O2	0.6136 (2)	1.16786 (7)	0.42474 (8)	0.0513 (4)
O3	0.80086 (19)	0.50774 (7)	0.53939 (8)	0.0327 (3)
H1	0.844 (3)	0.4741 (13)	0.5221 (13)	0.049*
H2	0.855 (3)	0.5404 (13)	0.5307 (13)	0.049*
O4	0.4919 (2)	0.53685 (7)	0.60006 (8)	0.0344 (3)
H3	0.591 (4)	0.5432 (13)	0.6368 (14)	0.052*
H4	0.423 (3)	0.5747 (13)	0.5993 (13)	0.052*
O5	0.7710 (4)	0.55277 (9)	0.05365 (11)	0.0879 (8)
O6	0.7924 (2)	0.53366 (8)	−0.05325 (9)	0.0507 (4)
H9	0.819 (4)	0.5542 (14)	−0.0882 (13)	0.076*
O7	0.8657 (3)	0.59789 (8)	−0.14700 (9)	0.0702 (6)
O8	0.9161 (2)	0.70368 (8)	−0.17320 (7)	0.0464 (4)
O9	0.9545 (2)	0.74468 (7)	0.20592 (7)	0.0419 (4)
H8	0.939 (4)	0.7691 (13)	0.2399 (15)	0.063*
O10	0.9735 (2)	0.84566 (7)	0.15526 (8)	0.0444 (4)
O11	1.04737 (18)	0.89852 (6)	0.00847 (7)	0.0349 (3)
O12	1.29187 (17)	0.84798 (6)	0.09494 (7)	0.0313 (3)
O13	0.8157 (3)	0.95061 (10)	0.21503 (10)	0.0555 (4)
H5	0.872 (5)	0.9152 (19)	0.199 (2)	0.105 (13)*
H6	0.816 (5)	0.9357 (17)	0.257 (2)	0.097 (12)*
O14	0.8680 (18)	1.0750 (5)	0.2965 (6)	0.109 (3)	0.25
H10	0.91 (3)	1.062 (10)	0.340 (4)	0.163*	0.25
H11	0.798 (10)	1.044 (3)	0.275 (10)	0.163*	0.25
N1	0.4598 (2)	0.60196 (7)	0.45273 (8)	0.0267 (3)
N2	0.3534 (2)	0.93790 (7)	0.31154 (8)	0.0253 (3)
C1	0.3529 (3)	0.61428 (9)	0.38216 (11)	0.0359 (4)
H1A	0.2941	0.5775	0.3525	0.043*
C2	0.3255 (3)	0.67884 (9)	0.35108 (11)	0.0360 (4)
H2A	0.2528	0.6848	0.3014	0.043*
C3	0.5401 (3)	0.65598 (9)	0.49434 (10)	0.0299 (4)
H3A	0.6167	0.6485	0.5433	0.036*
C4	0.5151 (3)	0.72233 (9)	0.46828 (10)	0.0301 (4)
H4A	0.5702	0.7584	0.4999	0.036*
C5	0.4079 (2)	0.73488 (8)	0.39504 (10)	0.0253 (4)
C6	0.3860 (2)	0.80580 (9)	0.36554 (10)	0.0256 (4)
C7	0.3945 (3)	0.81976 (9)	0.29649 (10)	0.0340 (4)
H7A	0.4100	0.7841	0.2672	0.041*
C8	0.3803 (3)	0.88552 (9)	0.27086 (10)	0.0343 (4)
H8A	0.3893	0.8942	0.2248	0.041*
C9	0.3598 (3)	0.86071 (9)	0.40711 (10)	0.0284 (4)
H9A	0.3547	0.8532	0.4540	0.034*
C10	0.3416 (3)	0.92569 (9)	0.37883 (10)	0.0288 (4)
H10A	0.3208	0.9619	0.4063	0.035*
C12	0.3409 (3)	1.00795 (8)	0.28392 (10)	0.0263 (4)
C13	0.2324 (3)	1.02160 (10)	0.21080 (10)	0.0355 (4)
H13A	0.1684	0.9866	0.1793	0.043*
C14	0.2213 (3)	1.08835 (10)	0.18574 (11)	0.0407 (5)
H14A	0.1504	1.0983	0.1367	0.049*
C15	0.3149 (3)	1.14040 (9)	0.23309 (10)	0.0330 (4)
H15A	0.3052	1.1852	0.2160	0.040*
C16	0.4233 (3)	1.12578 (9)	0.30622 (10)	0.0261 (4)
C17	0.4371 (2)	1.05870 (9)	0.33179 (9)	0.0265 (4)
H17A	0.5103	1.0483	0.3805	0.032*
C18	0.5277 (3)	1.17943 (9)	0.36038 (10)	0.0290 (4)
C19	0.8122 (3)	0.57302 (10)	0.00281 (12)	0.0367 (5)
C20	0.8992 (3)	0.65999 (10)	−0.13012 (10)	0.0311 (4)
C21	0.9692 (2)	0.78374 (9)	0.15265 (10)	0.0272 (4)
C22	1.1268 (2)	0.84837 (8)	0.04705 (9)	0.0240 (4)
C23	0.8857 (2)	0.64591 (9)	0.00489 (10)	0.0252 (4)
C24	0.9082 (2)	0.67918 (9)	0.07170 (9)	0.0262 (4)
H24A	0.8778	0.6557	0.1080	0.031*
C25	0.9740 (2)	0.74564 (9)	0.08605 (9)	0.0231 (4)
C26	1.0261 (2)	0.78040 (8)	0.03287 (9)	0.0223 (3)
C27	0.9965 (2)	0.74906 (9)	−0.03482 (9)	0.0245 (4)
H27A	1.0256	0.7733	−0.0710	0.029*
C28	0.9254 (2)	0.68298 (9)	−0.05120 (9)	0.0237 (4)

	U11	U22	U33	U12	U13	U23
Zn1	0.03018 (16)	0.01496 (15)	0.02675 (16)	0.00253 (11)	0.01013 (12)	0.00130 (11)
O1	0.0654 (10)	0.0207 (7)	0.0339 (8)	−0.0122 (7)	0.0046 (7)	0.0038 (6)
O2	0.0864 (12)	0.0321 (8)	0.0254 (8)	−0.0156 (8)	0.0070 (8)	0.0014 (6)
O3	0.0322 (7)	0.0228 (7)	0.0456 (8)	−0.0012 (6)	0.0167 (6)	−0.0025 (6)
O4	0.0456 (8)	0.0273 (7)	0.0299 (7)	0.0110 (6)	0.0125 (6)	−0.0006 (6)
O5	0.178 (2)	0.0368 (10)	0.0895 (14)	−0.0447 (12)	0.0982 (16)	−0.0147 (9)
O6	0.0767 (11)	0.0299 (8)	0.0470 (9)	−0.0207 (8)	0.0234 (8)	−0.0105 (7)
O7	0.1403 (18)	0.0379 (9)	0.0362 (9)	−0.0227 (10)	0.0359 (10)	−0.0152 (7)
O8	0.0765 (11)	0.0419 (9)	0.0260 (7)	−0.0017 (8)	0.0243 (7)	0.0016 (6)
O9	0.0714 (10)	0.0359 (8)	0.0269 (7)	−0.0035 (7)	0.0281 (7)	−0.0002 (6)
O10	0.0751 (11)	0.0284 (8)	0.0404 (8)	−0.0017 (7)	0.0335 (8)	−0.0051 (6)
O11	0.0391 (7)	0.0211 (7)	0.0442 (8)	0.0020 (6)	0.0141 (6)	0.0095 (6)
O12	0.0334 (7)	0.0211 (6)	0.0359 (7)	−0.0047 (5)	0.0076 (6)	0.0014 (5)
O13	0.0707 (11)	0.0586 (11)	0.0343 (9)	0.0133 (9)	0.0147 (8)	0.0069 (8)
O14	0.142 (9)	0.066 (6)	0.087 (7)	0.003 (6)	0.001 (7)	−0.007 (5)
N1	0.0324 (8)	0.0173 (7)	0.0303 (8)	0.0015 (6)	0.0108 (7)	0.0009 (6)
N2	0.0356 (8)	0.0162 (7)	0.0235 (7)	0.0000 (6)	0.0094 (6)	0.0008 (6)
C1	0.0510 (12)	0.0183 (9)	0.0312 (10)	−0.0001 (8)	0.0053 (9)	−0.0028 (8)
C2	0.0529 (12)	0.0205 (9)	0.0272 (10)	0.0028 (8)	0.0047 (9)	0.0012 (8)
C3	0.0334 (10)	0.0235 (9)	0.0282 (10)	−0.0008 (8)	0.0051 (8)	0.0033 (7)
C4	0.0363 (10)	0.0184 (9)	0.0313 (10)	−0.0048 (7)	0.0065 (8)	−0.0022 (7)
C5	0.0310 (9)	0.0172 (8)	0.0292 (9)	0.0023 (7)	0.0127 (8)	0.0018 (7)
C6	0.0294 (9)	0.0187 (9)	0.0270 (9)	−0.0001 (7)	0.0078 (7)	−0.0003 (7)
C7	0.0573 (12)	0.0190 (9)	0.0288 (10)	0.0031 (8)	0.0189 (9)	−0.0033 (7)
C8	0.0582 (12)	0.0233 (9)	0.0255 (10)	0.0008 (9)	0.0198 (9)	−0.0006 (8)
C9	0.0421 (10)	0.0215 (9)	0.0242 (9)	0.0005 (8)	0.0148 (8)	0.0013 (7)
C10	0.0428 (11)	0.0201 (9)	0.0268 (9)	0.0015 (8)	0.0162 (8)	−0.0028 (7)
C12	0.0360 (10)	0.0174 (9)	0.0263 (9)	0.0006 (7)	0.0119 (8)	0.0035 (7)
C13	0.0464 (11)	0.0254 (10)	0.0271 (10)	−0.0056 (8)	0.0032 (9)	−0.0015 (8)
C14	0.0528 (13)	0.0314 (11)	0.0254 (10)	−0.0017 (9)	−0.0021 (9)	0.0072 (8)
C15	0.0443 (11)	0.0201 (9)	0.0312 (10)	−0.0003 (8)	0.0091 (9)	0.0070 (8)
C16	0.0340 (9)	0.0198 (9)	0.0260 (9)	0.0000 (7)	0.0123 (8)	0.0021 (7)
C17	0.0342 (10)	0.0228 (9)	0.0217 (9)	0.0005 (7)	0.0089 (7)	0.0030 (7)
C18	0.0393 (10)	0.0227 (9)	0.0278 (10)	−0.0021 (8)	0.0154 (8)	0.0013 (7)
C19	0.0467 (12)	0.0244 (10)	0.0439 (12)	−0.0072 (9)	0.0221 (10)	−0.0011 (9)
C20	0.0374 (10)	0.0316 (10)	0.0240 (9)	0.0008 (8)	0.0104 (8)	−0.0018 (8)
C21	0.0280 (9)	0.0308 (10)	0.0239 (9)	−0.0018 (7)	0.0104 (7)	0.0005 (7)
C22	0.0314 (9)	0.0191 (9)	0.0260 (9)	−0.0012 (7)	0.0157 (8)	0.0000 (7)
C23	0.0278 (9)	0.0215 (9)	0.0267 (9)	−0.0029 (7)	0.0102 (7)	0.0004 (7)
C24	0.0311 (9)	0.0266 (9)	0.0240 (9)	−0.0022 (7)	0.0134 (7)	0.0048 (7)
C25	0.0245 (8)	0.0241 (9)	0.0203 (8)	−0.0009 (7)	0.0073 (7)	0.0010 (7)
C26	0.0243 (8)	0.0196 (8)	0.0232 (8)	0.0004 (7)	0.0087 (7)	0.0018 (7)
C27	0.0301 (9)	0.0227 (9)	0.0233 (9)	−0.0012 (7)	0.0124 (7)	0.0045 (7)
C28	0.0258 (9)	0.0234 (9)	0.0216 (9)	0.0006 (7)	0.0077 (7)	0.0006 (7)

Zn1—O4	2.0798 (13)	C4—C5	1.382 (3)
Zn1—O3	2.1335 (14)	C4—H4A	0.9300
Zn1—N1	2.1689 (14)	C5—C6	1.486 (2)
O1—C18	1.321 (2)	C6—C7	1.382 (3)
O1—H7	0.88 (3)	C6—C9	1.394 (2)
O2—C18	1.204 (2)	C7—C8	1.368 (3)
O3—H1	0.85 (3)	C7—H7A	0.9300
O3—H2	0.81 (3)	C8—H8A	0.9300
O4—H3	0.84 (3)	C9—C10	1.371 (2)
O4—H4	0.90 (3)	C9—H9A	0.9300
O5—C19	1.195 (2)	C10—H10A	0.9300
O6—C19	1.292 (2)	C12—C17	1.377 (2)
O6—H9	0.867 (17)	C12—C13	1.387 (3)
O7—C20	1.260 (2)	C13—C14	1.384 (3)
O8—C20	1.229 (2)	C13—H13A	0.9300
O9—C21	1.315 (2)	C14—C15	1.385 (3)
O9—H8	0.85 (3)	C14—H14A	0.9300
O10—C21	1.212 (2)	C15—C16	1.390 (3)
O11—C22	1.250 (2)	C15—H15A	0.9300
O12—C22	1.266 (2)	C16—C17	1.392 (2)
O13—H5	0.92 (4)	C16—C18	1.496 (2)
O13—H6	0.87 (4)	C17—H17A	0.9300
O14—H10	0.82 (2)	C19—C23	1.525 (2)
O14—H11	0.82 (2)	C20—C28	1.531 (2)
N1—C3	1.337 (2)	C21—C25	1.496 (2)
N1—C1	1.339 (2)	C22—C26	1.508 (2)
N2—C8	1.348 (2)	C23—C24	1.399 (2)
N2—C10	1.352 (2)	C23—C28	1.418 (2)
N2—C12	1.460 (2)	C24—C25	1.384 (2)
C1—C2	1.382 (3)	C24—H24A	0.9300
C1—H1A	0.9300	C25—C26	1.396 (2)
C2—C5	1.392 (3)	C26—C27	1.387 (2)
C2—H2A	0.9300	C27—C28	1.392 (2)
C3—C4	1.380 (2)	C27—H27A	0.9300
C3—H3A	0.9300
O4i—Zn1—O4	180.0	C10—C9—H9A	120.0
O4i—Zn1—O3i	91.02 (6)	C6—C9—H9A	120.0
O4—Zn1—O3i	88.98 (6)	N2—C10—C9	120.95 (16)
O4i—Zn1—O3	88.98 (6)	N2—C10—H10A	119.5
O4—Zn1—O3	91.02 (6)	C9—C10—H10A	119.5
O3i—Zn1—O3	180.0	C17—C12—C13	121.91 (16)
O4i—Zn1—N1	88.50 (5)	C17—C12—N2	118.68 (15)
O4—Zn1—N1	91.50 (5)	C13—C12—N2	119.41 (16)
O3i—Zn1—N1	86.58 (5)	C14—C13—C12	118.60 (17)
O3—Zn1—N1	93.42 (5)	C14—C13—H13A	120.7
O4i—Zn1—N1i	91.50 (5)	C12—C13—H13A	120.7
O4—Zn1—N1i	88.50 (5)	C13—C14—C15	120.55 (18)
O3i—Zn1—N1i	93.42 (5)	C13—C14—H14A	119.7
O3—Zn1—N1i	86.58 (5)	C15—C14—H14A	119.7
N1—Zn1—N1i	180.00 (8)	C14—C15—C16	120.09 (17)
C18—O1—H7	113.0 (17)	C14—C15—H15A	120.0
Zn1—O3—H1	107.9 (16)	C16—C15—H15A	120.0
Zn1—O3—H2	122.5 (17)	C15—C16—C17	119.83 (16)
H1—O3—H2	104 (2)	C15—C16—C18	122.93 (16)
Zn1—O4—H3	121.7 (17)	C17—C16—C18	117.23 (16)
Zn1—O4—H4	118.2 (15)	C12—C17—C16	119.02 (16)
H3—O4—H4	103 (2)	C12—C17—H17A	120.5
C19—O6—H9	112 (2)	C16—C17—H17A	120.5
C21—O9—H8	110.3 (18)	O2—C18—O1	122.97 (17)
H5—O13—H6	102 (3)	O2—C18—C16	123.40 (16)
H10—O14—H11	104 (10)	O1—C18—C16	113.63 (16)
C3—N1—C1	116.98 (15)	O5—C19—O6	120.08 (19)
C3—N1—Zn1	120.43 (12)	O5—C19—C23	119.00 (18)
C1—N1—Zn1	122.58 (12)	O6—C19—C23	120.91 (17)
C8—N2—C10	119.85 (15)	O8—C20—O7	123.68 (18)
C8—N2—C12	120.28 (14)	O8—C20—C28	117.35 (16)
C10—N2—C12	119.85 (14)	O7—C20—C28	118.95 (16)
N1—C1—C2	123.42 (17)	O10—C21—O9	123.79 (17)
N1—C1—H1A	118.3	O10—C21—C25	121.67 (16)
C2—C1—H1A	118.3	O9—C21—C25	114.51 (16)
C1—C2—C5	119.20 (17)	O11—C22—O12	125.74 (16)
C1—C2—H2A	120.4	O11—C22—C26	118.48 (15)
C5—C2—H2A	120.4	O12—C22—C26	115.63 (15)
N1—C3—C4	123.26 (17)	C24—C23—C28	118.29 (15)
N1—C3—H3A	118.4	C24—C23—C19	112.65 (15)
C4—C3—H3A	118.4	C28—C23—C19	129.02 (16)
C3—C4—C5	119.72 (17)	C25—C24—C23	122.71 (15)
C3—C4—H4A	120.1	C25—C24—H24A	118.6
C5—C4—H4A	120.1	C23—C24—H24A	118.6
C4—C5—C2	117.37 (16)	C24—C25—C26	118.93 (15)
C4—C5—C6	120.26 (16)	C24—C25—C21	121.64 (15)
C2—C5—C6	122.36 (16)	C26—C25—C21	119.03 (15)
C7—C6—C9	117.70 (16)	C27—C26—C25	118.78 (15)
C7—C6—C5	121.10 (15)	C27—C26—C22	117.73 (15)
C9—C6—C5	121.18 (16)	C25—C26—C22	123.32 (15)
C8—C7—C6	120.62 (17)	C26—C27—C28	123.08 (15)
C8—C7—H7A	119.7	C26—C27—H27A	118.5
C6—C7—H7A	119.7	C28—C27—H27A	118.5
N2—C8—C7	120.86 (17)	C27—C28—C23	117.96 (15)
N2—C8—H8A	119.6	C27—C28—C20	113.79 (15)
C7—C8—H8A	119.6	C23—C28—C20	128.25 (16)
C10—C9—C6	119.99 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H7···O12ii	0.87 (2)	1.80 (3)	2.656 (3)	164 (3)
O3—H1···O11iii	0.85 (2)	1.88 (3)	2.732 (2)	175 (3)
O3—H2···O11iv	0.81 (3)	2.03 (2)	2.820 (4)	163 (2)
O4—H3···O13iv	0.84 (2)	1.84 (3)	2.677 (6)	175 (3)
O4—H4···O12v	0.90 (3)	1.79 (4)	2.694 (2)	177 (4)
O6—H9···O7	0.87 (3)	1.56 (3)	2.418 (2)	174 (3)
O9—H8···O8iv	0.85 (3)	1.82 (3)	2.646 (3)	163 (4)
O13—H5···O10	0.92 (4)	1.90 (2)	2.813 (3)	174 (3)
O13—H6···O7iv	0.87 (4)	1.86 (4)	2.723 (2)	169 (3)
O14—H11···O13	0.82 (2)	2.18 (2)	2.846 (2)	138 (2)
C7—H7A···O1vi	0.93	2.30	3.155 (2)	153
C8—H8A···O12vii	0.93	2.52	3.302 (2)	142
C9—H9A···O2viii	0.93	2.30	3.225 (2)	172
C10—H10A···O5ix	0.93	2.15	3.060 (3)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H7⋯O12i	0.87 (2)	1.80 (3)	2.656 (3)	164 (3)
O3—H1⋯O11ii	0.85 (2)	1.88 (3)	2.732 (2)	175 (3)
O3—H2⋯O11iii	0.81 (3)	2.03 (2)	2.820 (4)	163 (2)
O4—H3⋯O13iii	0.84 (2)	1.84 (3)	2.677 (6)	175 (3)
O4—H4⋯O12iv	0.90 (3)	1.79 (4)	2.694 (2)	177 (4)
O6—H9⋯O7	0.87 (3)	1.56 (3)	2.418 (2)	174 (3)
O9—H8⋯O8iii	0.85 (3)	1.82 (3)	2.646 (3)	163 (4)
O13—H5⋯O10	0.92 (4)	1.90 (2)	2.813 (3)	174 (3)
O13—H6⋯O7iii	0.87 (4)	1.86 (4)	2.723 (2)	169 (3)
O14—H11⋯O13	0.82 (2)	2.18 (2)	2.846 (2)	138 (2)
C7—H7A⋯O1v	0.93	2.30	3.155 (2)	153
C8—H8A⋯O12vi	0.93	2.52	3.302 (2)	142
C9—H9A⋯O2vii	0.93	2.30	3.225 (2)	172
C10—H10A⋯O5viii	0.93	2.15	3.060 (3)	167

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