3,4-Dihydr-oxy-N'-(2-hydroxy-benzyl-idene)benzohydrazide-methanol-water (2/1/3).

The asymmetric unit of the title compound, C(14)H(12)N(2)O(4)·0.5CH(4)O·1.5H(2)O, consists of two Schiff base mol-ecules, three water mol-ecules and one methanol mol-ecule. The dihedral angle between the two benzene rings is 7.8 (2)° in one of the mol-ecules and 4.0 (2)° in the other. Intra-molecular O-H⋯O and O-H⋯N hydrogen bonds are observed. Mol-ecules are linked into a three-dimensional network by O-H⋯O and N-H⋯O inter-molecular hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Brückner et al. (2000 ▶); Harrop et al. (2003 ▶); Ren et al. (2002 ▶). For related structures, see: Diao (2007 ▶); Diao et al. (2007 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

C14H12N2O4·0.5CH4O·1.5H2O

M = 315.30

Triclinic,

a = 10.707 (2) Å

b = 11.994 (2) Å

c = 14.103 (3) Å

α = 111.56 (3)°

β = 103.13 (3)°

γ = 104.72 (3)°

V = 1522.2 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 (2) K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.982, T max = 0.984

9348 measured reflections

6429 independent reflections

2812 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.144

S = 0.97

6429 reflections

438 parameters

11 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065038/ci2538sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065038/ci2538Isup2.hkl

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

C14H12N2O4·0.5CH4O·1.5H2O	Z = 4
Mr = 315.30	F000 = 664
Triclinic, P1	Dx = 1.376 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.707 (2) Å	Cell parameters from 1027 reflections
b = 11.994 (2) Å	θ = 2.6–24.4º
c = 14.103 (3) Å	µ = 0.11 mm−1
α = 111.56 (3)º	T = 298 (2) K
β = 103.13 (3)º	Block, yellow
γ = 104.72 (3)º	0.17 × 0.15 × 0.15 mm
V = 1522.2 (8) Å3

Bruker SMART CCD area-detector diffractometer	6429 independent reflections
Radiation source: fine-focus sealed tube	2812 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 298(2) K	θmax = 26.9º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −13→9
Tmin = 0.982, Tmax = 0.984	k = −14→15
9348 measured reflections	l = −14→17

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)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.001
6429 reflections	Δρmax = 0.17 e Å−3
438 parameters	Δρmin = −0.21 e Å−3
11 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.7795 (2)	0.64000 (17)	1.35513 (13)	0.0587 (6)
H1	0.7625	0.5633	1.3388	0.088*
O2	0.7267 (2)	0.85547 (16)	1.37077 (14)	0.0528 (5)
H2	0.7490	0.8323	1.4179	0.079*
O3	0.7116 (2)	0.39011 (18)	0.96456 (14)	0.0609 (6)
O4	0.6696 (2)	0.19447 (18)	0.67631 (15)	0.0605 (6)
H4	0.6723	0.2551	0.7296	0.091*
O5	0.6555 (2)	0.13711 (18)	−0.10815 (14)	0.0675 (6)
H5	0.6701	0.2132	−0.0932	0.101*
O6	0.7472 (2)	−0.05612 (18)	−0.11851 (15)	0.0635 (6)
H6	0.7496	−0.0212	−0.1586	0.095*
O7	0.71818 (18)	0.38404 (17)	0.28249 (13)	0.0490 (5)
O8	0.7971 (2)	0.60616 (18)	0.57457 (15)	0.0625 (6)
H8	0.7958	0.5464	0.5214	0.094*
O9	0.8032 (2)	0.04122 (18)	0.73419 (16)	0.0581 (5)
H9	0.7470	0.0701	0.7128	0.087*
O10	0.5614 (2)	0.6868 (2)	0.83236 (18)	0.0619 (6)
O11	0.8239 (2)	0.84887 (19)	0.56226 (15)	0.0563 (6)
O12	0.9056 (2)	0.11266 (19)	0.42584 (19)	0.0669 (6)
N1	0.6301 (2)	0.4906 (2)	0.87321 (17)	0.0401 (5)
N2	0.6220 (2)	0.3958 (2)	0.77792 (17)	0.0406 (5)
N3	0.8292 (2)	0.30112 (19)	0.37667 (17)	0.0396 (5)
N4	0.8380 (2)	0.39822 (19)	0.47159 (16)	0.0382 (5)
C1	0.6883 (2)	0.5837 (2)	1.06912 (19)	0.0370 (6)
C2	0.7299 (2)	0.5671 (2)	1.16190 (19)	0.0425 (7)
H2A	0.7506	0.4945	1.1559	0.051*
C3	0.7415 (3)	0.6543 (2)	1.2623 (2)	0.0404 (6)
C4	0.7141 (3)	0.7644 (2)	1.2724 (2)	0.0401 (6)
C5	0.6716 (3)	0.7821 (2)	1.1813 (2)	0.0461 (7)
H5A	0.6512	0.8549	1.1877	0.055*
C6	0.6588 (3)	0.6929 (2)	1.0802 (2)	0.0464 (7)
H6A	0.6303	0.7063	1.0192	0.056*
C7	0.6776 (3)	0.4813 (3)	0.9654 (2)	0.0418 (7)
C8	0.5749 (2)	0.4005 (3)	0.6887 (2)	0.0431 (7)
H8A	0.5451	0.4669	0.6888	0.052*
C9	0.5675 (2)	0.3036 (3)	0.58771 (19)	0.0399 (6)
C10	0.6148 (3)	0.2049 (3)	0.5842 (2)	0.0457 (7)
C11	0.6070 (3)	0.1131 (3)	0.4859 (2)	0.0602 (9)
H11	0.6400	0.0481	0.4845	0.072*
C12	0.5506 (3)	0.1181 (3)	0.3907 (3)	0.0722 (11)
H12	0.5436	0.0554	0.3245	0.087*
C13	0.5047 (3)	0.2150 (4)	0.3926 (2)	0.0697 (10)
H13	0.4679	0.2187	0.3280	0.084*
C14	0.5126 (3)	0.3074 (3)	0.4900 (2)	0.0555 (8)
H14	0.4809	0.3729	0.4904	0.067*
C15	0.7553 (3)	0.1977 (2)	0.17858 (19)	0.0389 (6)
C16	0.7038 (3)	0.2094 (2)	0.0849 (2)	0.0447 (7)
H16	0.6703	0.2747	0.0890	0.054*
C17	0.7011 (3)	0.1264 (3)	−0.0143 (2)	0.0475 (7)
C18	0.7470 (3)	0.0272 (2)	−0.0213 (2)	0.0481 (7)
C19	0.7935 (3)	0.0113 (3)	0.0699 (2)	0.0581 (8)
H19	0.8221	−0.0571	0.0645	0.070*
C20	0.7984 (3)	0.0957 (2)	0.1699 (2)	0.0517 (8)
H20	0.8306	0.0843	0.2314	0.062*
C21	0.7657 (3)	0.3000 (2)	0.2826 (2)	0.0385 (6)
C22	0.8895 (2)	0.3959 (2)	0.5612 (2)	0.0406 (6)
H22	0.9212	0.3306	0.5616	0.049*
C23	0.8987 (2)	0.4949 (2)	0.6626 (2)	0.0404 (7)
C24	0.8529 (3)	0.5961 (3)	0.6665 (2)	0.0462 (7)
C25	0.8627 (3)	0.6882 (3)	0.7647 (2)	0.0606 (8)
H25	0.8320	0.7546	0.7667	0.073*
C26	0.9175 (3)	0.6818 (3)	0.8592 (3)	0.0686 (10)
H26	0.9241	0.7445	0.9252	0.082*
C27	0.9630 (3)	0.5839 (3)	0.8583 (2)	0.0653 (9)
H27	0.9999	0.5801	0.9229	0.078*
C28	0.9532 (3)	0.4917 (3)	0.7604 (2)	0.0518 (8)
H28	0.9839	0.4256	0.7596	0.062*
C29	0.9365 (3)	0.1399 (4)	0.7883 (3)	0.1063 (14)
H29A	0.9356	0.2106	0.8488	0.159*
H29B	0.9623	0.1696	0.7384	0.159*
H29C	1.0019	0.1066	0.8145	0.159*
H3	0.857 (3)	0.238 (2)	0.382 (2)	0.080*
H11B	0.799 (3)	0.897 (2)	0.6091 (19)	0.080*
H12B	0.852 (2)	0.0381 (15)	0.411 (2)	0.080*
H1A	0.608 (3)	0.5579 (19)	0.871 (2)	0.080*
H12A	0.9848 (14)	0.110 (3)	0.428 (2)	0.080*
H11A	0.806 (3)	0.7774 (15)	0.565 (2)	0.080*
H10A	0.613 (2)	0.7585 (17)	0.840 (2)	0.080*
H10B	0.4781 (12)	0.677 (3)	0.804 (2)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0975 (16)	0.0432 (11)	0.0340 (11)	0.0319 (12)	0.0162 (10)	0.0165 (9)
O2	0.0792 (14)	0.0403 (11)	0.0418 (11)	0.0273 (10)	0.0260 (11)	0.0157 (9)
O3	0.1012 (16)	0.0528 (13)	0.0427 (12)	0.0477 (12)	0.0267 (11)	0.0225 (10)
O4	0.0862 (15)	0.0518 (13)	0.0495 (13)	0.0376 (12)	0.0249 (12)	0.0205 (11)
O5	0.1172 (18)	0.0582 (13)	0.0381 (12)	0.0494 (14)	0.0273 (11)	0.0220 (10)
O6	0.1113 (17)	0.0439 (12)	0.0450 (12)	0.0406 (12)	0.0357 (12)	0.0174 (10)
O7	0.0684 (13)	0.0426 (11)	0.0432 (11)	0.0319 (10)	0.0213 (9)	0.0185 (9)
O8	0.0940 (16)	0.0526 (13)	0.0508 (13)	0.0424 (12)	0.0278 (12)	0.0222 (11)
O9	0.0649 (14)	0.0559 (13)	0.0523 (13)	0.0294 (11)	0.0210 (11)	0.0185 (10)
O10	0.0650 (14)	0.0575 (14)	0.0714 (15)	0.0288 (12)	0.0174 (13)	0.0375 (13)
O11	0.0738 (14)	0.0496 (13)	0.0485 (13)	0.0278 (12)	0.0303 (10)	0.0168 (11)
O12	0.0593 (14)	0.0522 (13)	0.0956 (16)	0.0269 (12)	0.0253 (14)	0.0371 (13)
N1	0.0532 (14)	0.0373 (13)	0.0330 (13)	0.0209 (11)	0.0183 (11)	0.0146 (11)
N2	0.0461 (14)	0.0429 (13)	0.0334 (13)	0.0182 (11)	0.0158 (10)	0.0157 (11)
N3	0.0494 (14)	0.0353 (13)	0.0382 (13)	0.0191 (11)	0.0202 (11)	0.0157 (11)
N4	0.0444 (13)	0.0343 (12)	0.0326 (13)	0.0145 (10)	0.0158 (10)	0.0107 (10)
C1	0.0433 (16)	0.0346 (15)	0.0330 (15)	0.0160 (12)	0.0144 (12)	0.0139 (12)
C2	0.0541 (17)	0.0385 (15)	0.0367 (16)	0.0246 (14)	0.0139 (13)	0.0155 (13)
C3	0.0493 (17)	0.0365 (16)	0.0343 (15)	0.0152 (13)	0.0132 (13)	0.0164 (13)
C4	0.0484 (17)	0.0315 (15)	0.0395 (16)	0.0143 (13)	0.0195 (13)	0.0133 (13)
C5	0.0668 (19)	0.0341 (16)	0.0479 (17)	0.0263 (14)	0.0255 (15)	0.0213 (14)
C6	0.0663 (19)	0.0428 (17)	0.0372 (16)	0.0245 (15)	0.0196 (14)	0.0218 (14)
C7	0.0511 (17)	0.0421 (17)	0.0423 (17)	0.0221 (14)	0.0210 (13)	0.0236 (14)
C8	0.0419 (16)	0.0460 (17)	0.0465 (17)	0.0165 (13)	0.0189 (13)	0.0240 (15)
C9	0.0363 (15)	0.0448 (17)	0.0320 (15)	0.0082 (13)	0.0118 (12)	0.0154 (13)
C10	0.0476 (17)	0.0429 (17)	0.0414 (17)	0.0103 (14)	0.0208 (14)	0.0150 (14)
C11	0.066 (2)	0.0478 (19)	0.059 (2)	0.0121 (16)	0.0345 (17)	0.0141 (16)
C12	0.074 (2)	0.060 (2)	0.043 (2)	−0.0081 (19)	0.0279 (18)	0.0009 (18)
C13	0.063 (2)	0.083 (3)	0.0344 (19)	−0.005 (2)	0.0102 (15)	0.0223 (19)
C14	0.0486 (18)	0.067 (2)	0.0442 (18)	0.0118 (16)	0.0135 (15)	0.0269 (17)
C15	0.0498 (16)	0.0331 (15)	0.0353 (15)	0.0158 (13)	0.0191 (13)	0.0144 (13)
C16	0.0624 (19)	0.0397 (16)	0.0397 (16)	0.0274 (14)	0.0214 (14)	0.0182 (14)
C17	0.066 (2)	0.0400 (17)	0.0391 (17)	0.0231 (15)	0.0198 (15)	0.0183 (14)
C18	0.072 (2)	0.0326 (16)	0.0368 (16)	0.0193 (15)	0.0221 (14)	0.0108 (13)
C19	0.094 (2)	0.0401 (17)	0.0498 (19)	0.0364 (17)	0.0301 (17)	0.0202 (15)
C20	0.082 (2)	0.0402 (17)	0.0418 (17)	0.0300 (16)	0.0247 (15)	0.0211 (14)
C21	0.0483 (17)	0.0343 (15)	0.0379 (16)	0.0162 (13)	0.0199 (13)	0.0181 (13)
C22	0.0368 (15)	0.0391 (16)	0.0443 (17)	0.0139 (13)	0.0146 (13)	0.0172 (14)
C23	0.0358 (15)	0.0408 (16)	0.0365 (16)	0.0082 (13)	0.0110 (12)	0.0143 (13)
C24	0.0454 (17)	0.0419 (17)	0.0424 (17)	0.0091 (14)	0.0170 (13)	0.0139 (14)
C25	0.068 (2)	0.0479 (19)	0.052 (2)	0.0184 (16)	0.0275 (17)	0.0067 (16)
C26	0.064 (2)	0.064 (2)	0.043 (2)	0.0083 (19)	0.0207 (17)	−0.0015 (17)
C27	0.056 (2)	0.082 (3)	0.0359 (18)	0.0100 (19)	0.0089 (15)	0.0192 (18)
C28	0.0489 (18)	0.0583 (19)	0.0454 (18)	0.0160 (15)	0.0149 (14)	0.0245 (16)
C29	0.066 (3)	0.096 (3)	0.126 (3)	0.015 (2)	0.010 (2)	0.043 (3)

O1—C3	1.367 (3)	C6—H6A	0.93
O1—H1	0.82	C8—C9	1.440 (3)
O2—C4	1.365 (3)	C8—H8A	0.93
O2—H2	0.82	C9—C10	1.390 (4)
O3—C7	1.234 (3)	C9—C14	1.392 (3)
O4—C10	1.363 (3)	C10—C11	1.386 (4)
O4—H4	0.82	C11—C12	1.372 (4)
O5—C17	1.368 (3)	C11—H11	0.93
O5—H5	0.82	C12—C13	1.365 (4)
O6—C18	1.368 (3)	C12—H12	0.93
O6—H6	0.82	C13—C14	1.380 (4)
O7—C21	1.240 (3)	C13—H13	0.93
O8—C24	1.361 (3)	C14—H14	0.93
O8—H8	0.82	C15—C16	1.384 (3)
O9—C29	1.416 (3)	C15—C20	1.388 (3)
O9—H9	0.82	C15—C21	1.484 (3)
O10—H10A	0.846 (10)	C16—C17	1.375 (3)
O10—H10B	0.85 (2)	C16—H16	0.93
O11—H11B	0.85 (3)	C17—C18	1.378 (4)
O11—H11A	0.85 (2)	C18—C19	1.370 (4)
O12—H12B	0.85 (2)	C19—C20	1.381 (4)
O12—H12A	0.85 (2)	C19—H19	0.93
N1—C7	1.341 (3)	C20—H20	0.93
N1—N2	1.372 (3)	C22—C23	1.447 (3)
N1—H1A	0.91 (3)	C22—H22	0.93
N2—C8	1.272 (3)	C23—C28	1.388 (3)
N3—C21	1.340 (3)	C23—C24	1.407 (4)
N3—N4	1.378 (3)	C24—C25	1.379 (4)
N3—H3	0.90 (3)	C25—C26	1.367 (4)
N4—C22	1.273 (3)	C25—H25	0.93
C1—C6	1.387 (3)	C26—C27	1.379 (4)
C1—C2	1.387 (3)	C26—H26	0.93
C1—C7	1.481 (3)	C27—C28	1.376 (4)
C2—C3	1.372 (3)	C27—H27	0.93
C2—H2A	0.93	C28—H28	0.93
C3—C4	1.388 (3)	C29—H29A	0.96
C4—C5	1.373 (3)	C29—H29B	0.96
C5—C6	1.383 (3)	C29—H29C	0.96
C5—H5A	0.93
C3—O1—H1	109.5	C12—C13—C14	120.4 (3)
C4—O2—H2	109.5	C12—C13—H13	119.8
C10—O4—H4	109.5	C14—C13—H13	119.8
C17—O5—H5	109.5	C13—C14—C9	120.6 (3)
C18—O6—H6	109.5	C13—C14—H14	119.7
C24—O8—H8	109.5	C9—C14—H14	119.7
C29—O9—H9	109.5	C16—C15—C20	118.5 (2)
H10A—O10—H10B	108 (2)	C16—C15—C21	116.7 (2)
H11B—O11—H11A	107 (2)	C20—C15—C21	124.7 (2)
H12B—O12—H12A	108 (2)	C17—C16—C15	121.4 (3)
C7—N1—N2	117.5 (2)	C17—C16—H16	119.3
C7—N1—H1A	123.7 (19)	C15—C16—H16	119.3
N2—N1—H1A	118.7 (19)	O5—C17—C16	123.3 (3)
C8—N2—N1	119.1 (2)	O5—C17—C18	117.2 (2)
C21—N3—N4	117.2 (2)	C16—C17—C18	119.5 (3)
C21—N3—H3	124.4 (19)	O6—C18—C19	119.2 (3)
N4—N3—H3	118.0 (18)	O6—C18—C17	120.9 (2)
C22—N4—N3	118.1 (2)	C19—C18—C17	119.9 (3)
C6—C1—C2	118.0 (2)	C18—C19—C20	120.8 (3)
C6—C1—C7	125.4 (2)	C18—C19—H19	119.6
C2—C1—C7	116.6 (2)	C20—C19—H19	119.6
C3—C2—C1	122.0 (3)	C19—C20—C15	119.9 (3)
C3—C2—H2A	119.0	C19—C20—H20	120.0
C1—C2—H2A	119.0	C15—C20—H20	120.0
O1—C3—C2	123.7 (2)	O7—C21—N3	120.5 (2)
O1—C3—C4	117.0 (2)	O7—C21—C15	120.6 (2)
C2—C3—C4	119.3 (2)	N3—C21—C15	118.9 (2)
O2—C4—C5	118.8 (2)	N4—C22—C23	119.9 (3)
O2—C4—C3	121.6 (2)	N4—C22—H22	120.1
C5—C4—C3	119.6 (2)	C23—C22—H22	120.1
C4—C5—C6	120.7 (3)	C28—C23—C24	117.7 (3)
C4—C5—H5A	119.7	C28—C23—C22	120.0 (3)
C6—C5—H5A	119.7	C24—C23—C22	122.3 (2)
C5—C6—C1	120.4 (2)	O8—C24—C25	117.9 (3)
C5—C6—H6A	119.8	O8—C24—C23	121.7 (2)
C1—C6—H6A	119.8	C25—C24—C23	120.4 (3)
O3—C7—N1	121.3 (2)	C26—C25—C24	120.0 (3)
O3—C7—C1	120.6 (2)	C26—C25—H25	120.0
N1—C7—C1	118.1 (2)	C24—C25—H25	120.0
N2—C8—C9	120.3 (3)	C25—C26—C27	121.0 (3)
N2—C8—H8A	119.8	C25—C26—H26	119.5
C9—C8—H8A	119.8	C27—C26—H26	119.5
C10—C9—C14	118.2 (3)	C28—C27—C26	119.1 (3)
C10—C9—C8	121.8 (2)	C28—C27—H27	120.4
C14—C9—C8	120.0 (3)	C26—C27—H27	120.4
O4—C10—C11	117.7 (3)	C27—C28—C23	121.7 (3)
O4—C10—C9	121.7 (2)	C27—C28—H28	119.2
C11—C10—C9	120.6 (3)	C23—C28—H28	119.2
C12—C11—C10	120.0 (3)	O9—C29—H29A	109.5
C12—C11—H11	120.0	O9—C29—H29B	109.5
C10—C11—H11	120.0	H29A—C29—H29B	109.5
C13—C12—C11	120.2 (3)	O9—C29—H29C	109.5
C13—C12—H12	119.9	H29A—C29—H29C	109.5
C11—C12—H12	119.9	H29B—C29—H29C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10B···O7i	0.85 (2)	1.96 (1)	2.793 (3)	168 (3)
O10—H10A···O6ii	0.85 (1)	2.10 (1)	2.938 (3)	173 (3)
O11—H11A···O8	0.85 (2)	2.09 (1)	2.925 (3)	170 (3)
O12—H12A···O11iii	0.85 (2)	1.94 (1)	2.770 (3)	165 (3)
N1—H1A···O10	0.91 (3)	1.96 (3)	2.844 (3)	167 (3)
O12—H12B···O2iv	0.85 (2)	2.04 (1)	2.889 (3)	177 (3)
O11—H11B···O9v	0.85 (3)	1.95 (3)	2.765 (3)	162 (3)
N3—H3···O12	0.90 (3)	1.96 (3)	2.845 (3)	165 (3)
O8—H8···N4	0.82	1.87	2.589 (3)	146
O6—H6···O9vi	0.82	2.04	2.834 (3)	161
O5—H5···O3vi	0.82	1.86	2.670 (3)	170
O4—H4···N2	0.82	1.84	2.561 (3)	146
O2—H2···O1	0.82	2.29	2.725 (3)	114
O2—H2···O11vii	0.82	1.93	2.703 (3)	158
O1—H1···O7vii	0.82	1.88	2.695 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10B⋯O7i	0.85 (2)	1.96 (1)	2.793 (3)	168 (3)
O10—H10A⋯O6ii	0.85 (1)	2.10 (1)	2.938 (3)	173 (3)
O11—H11A⋯O8	0.85 (2)	2.09 (1)	2.925 (3)	170 (3)
O12—H12A⋯O11iii	0.85 (2)	1.94 (1)	2.770 (3)	165 (3)
N1—H1A⋯O10	0.91 (3)	1.96 (3)	2.844 (3)	167 (3)
O12—H12B⋯O2iv	0.85 (2)	2.04 (1)	2.889 (3)	177 (3)
O11—H11B⋯O9v	0.85 (3)	1.95 (3)	2.765 (3)	162 (3)
N3—H3⋯O12	0.90 (3)	1.96 (3)	2.845 (3)	165 (3)
O8—H8⋯N4	0.82	1.87	2.589 (3)	146
O6—H6⋯O9vi	0.82	2.04	2.834 (3)	161
O5—H5⋯O3vi	0.82	1.86	2.670 (3)	170
O4—H4⋯N2	0.82	1.84	2.561 (3)	146
O2—H2⋯O1	0.82	2.29	2.725 (3)	114
O2—H2⋯O11vii	0.82	1.93	2.703 (3)	158
O1—H1⋯O7vii	0.82	1.88	2.695 (3)	172

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