4-Hy-droxy-2-methyl-1,1-dioxo-2H-1λ,2- benzothia-zine-3-carb-oxy-lic acid hemihydrate.

In the title compound, C(10)H(9)NO(5)S·0.5H(2)O, two geometrically different organic mol-ecules are present. The benzene rings and the carboxyl-ate groups are oriented at dihedral angles of 13.44 (4) and 21.15 (18)°. In both mol-ecules, an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, both moleucles form inversion dimers linked by pairs of O-H⋯O hydrogen bonds to generate R(2) (2)(8) loops. The dimers are consolidated into chains extending along [100] by bridging O-H⋯O hydrogen bonds from the water mol-ecule. A weak C-H⋯O hydrogen bond also occurs.

Related literature

For background to non-steroidal anti-inflammatory drugs, see: Akram et al. (2008 ▶); Foye et al. (1995 ▶); Lombardino et al. (1971 ▶, 1973 ▶); Siddiqui, Ahmad, Siddiqui et al. (2008 ▶); Siddiqui, Ahmad, Tariq et al. (2008 ▶). For a related structure, see: Golič & Leban (1987 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C10H9NO5S·0.5H2O

M = 264.25

Triclinic,

a = 7.1837 (2) Å

b = 8.5847 (3) Å

c = 17.9814 (4) Å

α = 87.605 (1)°

β = 89.713 (2)°

γ = 87.174 (1)°

V = 1106.59 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.915, T max = 0.938

15712 measured reflections

4317 independent reflections

3468 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.097

S = 1.03

4317 reflections

295 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812004291/hb6618sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004291/hb6618Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004291/hb6618Isup3.cml

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

C10H9NO5S·0.5H2O	Z = 4
Mr = 264.25	F(000) = 548
Triclinic, P1	Dx = 1.586 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1837 (2) Å	Cell parameters from 3468 reflections
b = 8.5847 (3) Å	θ = 2.3–26.0°
c = 17.9814 (4) Å	µ = 0.31 mm−1
α = 87.605 (1)°	T = 296 K
β = 89.713 (2)°	Prism, light green
γ = 87.174 (1)°	0.35 × 0.25 × 0.22 mm
V = 1106.59 (6) Å3

Bruker Kappa APEXII CCD diffractometer	4317 independent reflections
Radiation source: fine-focus sealed tube	3468 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 8.00 pixels mm-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −7→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→10
Tmin = 0.915, Tmax = 0.938	l = −22→22
15712 measured reflections

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0439P)2 + 0.3985P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4317 reflections	Δρmax = 0.32 e Å−3
295 parameters	Δρmin = −0.32 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: 0.0115 (13)

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.

	x	y	z	Uiso*/Ueq
S1	0.73268 (7)	0.47997 (5)	0.36202 (3)	0.0326 (2)
O1	1.0126 (2)	0.78588 (17)	0.48912 (8)	0.0460 (5)
O2	0.9190 (2)	0.99420 (16)	0.41728 (8)	0.0487 (5)
O3	0.7800 (2)	0.95223 (16)	0.28936 (8)	0.0429 (5)
O4	0.56659 (19)	0.53462 (17)	0.39886 (8)	0.0434 (5)
O5	0.7877 (2)	0.31809 (15)	0.36788 (8)	0.0433 (5)
N1	0.9045 (2)	0.57982 (17)	0.39058 (8)	0.0318 (5)
C1	0.9390 (3)	0.8508 (2)	0.42875 (11)	0.0374 (7)
C2	0.8833 (3)	0.7439 (2)	0.37332 (10)	0.0318 (6)
C3	0.8093 (3)	0.7998 (2)	0.30725 (10)	0.0318 (6)
C4	0.7527 (3)	0.6968 (2)	0.24926 (10)	0.0318 (6)
C5	0.7316 (3)	0.7497 (3)	0.17540 (11)	0.0396 (7)
C6	0.6781 (3)	0.6499 (3)	0.12229 (11)	0.0458 (8)
C7	0.6430 (3)	0.4970 (3)	0.14134 (12)	0.0462 (8)
C8	0.6621 (3)	0.4403 (3)	0.21428 (11)	0.0407 (7)
C9	0.7164 (3)	0.5410 (2)	0.26757 (10)	0.0328 (6)
C10	1.09513 (6)	0.50694 (9)	0.39024 (3)	0.0442 (7)
S2	0.34876 (5)	1.12692 (4)	0.12496 (2)	0.0377 (2)
O6	0.36746 (6)	1.17536 (7)	0.35142 (3)	0.0544 (6)
O7	0.37431 (6)	0.91858 (7)	0.37872 (3)	0.0550 (6)
O8	0.31763 (5)	0.73224 (5)	0.27403 (4)	0.0476 (5)
O9	0.54647 (5)	1.10602 (4)	0.13153 (2)	0.0479 (5)
O10	0.27227 (5)	1.25250 (4)	0.07867 (2)	0.0530 (6)
N2	0.26231 (5)	1.14344 (4)	0.20849 (2)	0.0361 (5)
C11	0.35007 (5)	1.03047 (5)	0.33412 (3)	0.0412 (7)
C12	0.29810 (5)	1.00779 (4)	0.25703 (2)	0.0352 (6)
C13	0.28734 (5)	0.86196 (5)	0.23138 (3)	0.0352 (6)
C14	0.24568 (5)	0.83233 (5)	0.15354 (3)	0.0363 (6)
C15	0.19471 (5)	0.68585 (5)	0.13242 (4)	0.0488 (8)
C16	0.1577 (3)	0.6612 (3)	0.05880 (15)	0.0585 (9)
C17	0.1707 (3)	0.7789 (3)	0.00546 (14)	0.0598 (9)
C18	0.2239 (3)	0.9247 (3)	0.02421 (12)	0.0511 (8)
C19	0.2620 (3)	0.9500 (2)	0.09812 (11)	0.0372 (6)
C20	0.0766 (3)	1.2219 (3)	0.21567 (13)	0.0530 (8)
O11	0.4465 (3)	0.2097 (2)	0.48986 (9)	0.0635 (7)
H1	1.038 (3)	0.854 (3)	0.5179 (13)	0.0552*
H3	0.816 (3)	1.001 (3)	0.3286 (13)	0.0514*
H5	0.75359	0.85293	0.16185	0.0475*
H6	0.66556	0.68614	0.07302	0.0549*
H7	0.60624	0.43125	0.10490	0.0554*
H8	0.63897	0.33706	0.22725	0.0488*
H10A	1.14009	0.50333	0.33994	0.0663*
H10B	1.09340	0.40282	0.41180	0.0663*
H10C	1.17576	0.56731	0.41874	0.0663*
H6A	0.39669	1.17567	0.39964	0.0652*
H8A	0.33841	0.76910	0.31793	0.0571*
H15	0.18570	0.60481	0.16802	0.0585*
H16	0.12344	0.56331	0.04515	0.0702*
H17	0.14353	0.76055	−0.04383	0.0717*
H18	0.23387	1.00439	−0.01205	0.0613*
H20A	0.05271	1.24259	0.26698	0.0795*
H20B	−0.01620	1.15579	0.19802	0.0795*
H20C	0.07219	1.31847	0.18667	0.0795*
H11A	0.453 (4)	0.294 (4)	0.5075 (17)	0.0762*
H11B	0.507 (4)	0.152 (3)	0.5209 (16)	0.0762*

	U11	U22	U33	U12	U13	U23
S1	0.0377 (3)	0.0276 (3)	0.0328 (3)	−0.0056 (2)	−0.0022 (2)	−0.0010 (2)
O1	0.0701 (10)	0.0310 (8)	0.0377 (8)	−0.0098 (7)	−0.0214 (7)	0.0008 (6)
O2	0.0744 (11)	0.0265 (8)	0.0457 (9)	−0.0063 (7)	−0.0213 (8)	−0.0001 (6)
O3	0.0589 (10)	0.0283 (8)	0.0412 (8)	−0.0037 (7)	−0.0138 (7)	0.0047 (6)
O4	0.0401 (8)	0.0479 (9)	0.0427 (8)	−0.0068 (7)	0.0066 (6)	−0.0051 (7)
O5	0.0575 (9)	0.0267 (8)	0.0456 (8)	−0.0047 (7)	−0.0087 (7)	0.0023 (6)
N1	0.0350 (9)	0.0247 (8)	0.0356 (9)	−0.0021 (7)	−0.0076 (7)	0.0014 (7)
C1	0.0440 (12)	0.0310 (12)	0.0374 (11)	−0.0070 (9)	−0.0078 (9)	0.0029 (9)
C2	0.0360 (10)	0.0255 (10)	0.0338 (10)	−0.0034 (8)	−0.0046 (8)	0.0020 (8)
C3	0.0327 (10)	0.0270 (10)	0.0357 (10)	−0.0028 (8)	−0.0009 (8)	0.0014 (8)
C4	0.0286 (10)	0.0338 (11)	0.0326 (10)	0.0005 (8)	−0.0021 (8)	0.0008 (8)
C5	0.0402 (11)	0.0423 (12)	0.0357 (11)	−0.0018 (9)	−0.0028 (9)	0.0048 (9)
C6	0.0468 (13)	0.0589 (15)	0.0311 (11)	0.0020 (11)	−0.0041 (9)	−0.0003 (10)
C7	0.0489 (13)	0.0524 (14)	0.0380 (12)	0.0010 (11)	−0.0087 (10)	−0.0138 (10)
C8	0.0424 (12)	0.0368 (12)	0.0435 (12)	−0.0008 (9)	−0.0056 (9)	−0.0090 (9)
C9	0.0308 (10)	0.0341 (11)	0.0334 (10)	0.0008 (8)	−0.0030 (8)	−0.0026 (8)
C10	0.0401 (12)	0.0345 (12)	0.0571 (14)	0.0004 (9)	−0.0016 (10)	0.0079 (10)
S2	0.0490 (3)	0.0330 (3)	0.0308 (3)	−0.0030 (2)	0.0016 (2)	0.0025 (2)
O6	0.0779 (12)	0.0512 (10)	0.0340 (8)	−0.0002 (8)	−0.0103 (8)	−0.0042 (7)
O7	0.0713 (11)	0.0566 (10)	0.0354 (8)	0.0034 (9)	−0.0033 (7)	0.0105 (8)
O8	0.0563 (10)	0.0377 (9)	0.0475 (9)	−0.0017 (7)	0.0050 (7)	0.0112 (7)
O9	0.0454 (9)	0.0476 (9)	0.0509 (9)	−0.0086 (7)	0.0081 (7)	0.0020 (7)
O10	0.0814 (12)	0.0390 (9)	0.0373 (8)	0.0008 (8)	−0.0052 (8)	0.0091 (7)
N2	0.0467 (10)	0.0312 (9)	0.0297 (9)	0.0020 (8)	0.0000 (7)	0.0009 (7)
C11	0.0430 (12)	0.0462 (13)	0.0336 (11)	0.0028 (10)	0.0028 (9)	0.0029 (10)
C12	0.0382 (11)	0.0363 (12)	0.0304 (10)	0.0015 (9)	0.0023 (8)	0.0038 (9)
C13	0.0328 (10)	0.0334 (11)	0.0384 (11)	0.0001 (9)	0.0048 (8)	0.0076 (9)
C14	0.0304 (10)	0.0345 (11)	0.0439 (11)	−0.0009 (9)	0.0043 (8)	−0.0032 (9)
C15	0.0429 (12)	0.0387 (13)	0.0653 (15)	−0.0065 (10)	0.0060 (11)	−0.0055 (11)
C16	0.0538 (15)	0.0506 (15)	0.0735 (18)	−0.0075 (12)	−0.0037 (12)	−0.0250 (14)
C17	0.0626 (16)	0.0646 (17)	0.0533 (15)	0.0035 (13)	−0.0080 (12)	−0.0242 (14)
C18	0.0618 (15)	0.0530 (15)	0.0384 (12)	0.0022 (12)	−0.0019 (10)	−0.0082 (11)
C19	0.0393 (11)	0.0346 (11)	0.0376 (11)	0.0021 (9)	0.0008 (9)	−0.0039 (9)
C20	0.0598 (15)	0.0465 (14)	0.0504 (14)	0.0160 (12)	0.0057 (11)	0.0017 (11)
O11	0.0951 (14)	0.0557 (12)	0.0398 (9)	0.0004 (11)	−0.0156 (9)	−0.0064 (8)

S1—O4	1.4302 (15)	C4—C9	1.401 (2)
S1—O5	1.4257 (14)	C5—C6	1.378 (3)
S1—N1	1.6339 (15)	C6—C7	1.378 (4)
S1—C9	1.7590 (19)	C7—C8	1.385 (3)
S2—N2	1.6314 (5)	C8—C9	1.387 (3)
S2—O9	1.4276 (5)	C5—H5	0.9300
S2—O10	1.4241 (5)	C6—H6	0.9300
S2—C19	1.7566 (18)	C7—H7	0.9300
O1—C1	1.302 (2)	C8—H8	0.9300
O2—C1	1.241 (2)	C10—H10C	0.9600
O3—C3	1.341 (2)	C10—H10A	0.9600
O1—H1	0.83 (2)	C10—H10B	0.9600
O3—H3	0.88 (2)	C11—C12	1.4607 (6)
O6—C11	1.3067 (7)	C12—C13	1.3580 (6)
O7—C11	1.2315 (7)	C13—C14	1.4679 (7)
O8—C13	1.3349 (7)	C14—C19	1.3977 (19)
O6—H6A	0.8900	C14—C15	1.3951 (6)
O8—H8A	0.8800	C15—C16	1.379 (3)
O11—H11B	0.84 (3)	C16—C17	1.370 (4)
O11—H11A	0.81 (3)	C17—C18	1.382 (4)
N1—C10	1.4774 (15)	C18—C19	1.386 (3)
N1—C2	1.431 (2)	C15—H15	0.9300
N2—C12	1.4394 (5)	C16—H16	0.9300
N2—C20	1.472 (2)	C17—H17	0.9300
C1—C2	1.453 (3)	C18—H18	0.9300
C2—C3	1.363 (3)	C20—H20C	0.9600
C3—C4	1.467 (3)	C20—H20A	0.9600
C4—C5	1.392 (3)	C20—H20B	0.9600
O4—S1—O5	119.32 (9)	C7—C6—H6	120.00
O4—S1—N1	107.88 (8)	C6—C7—H7	120.00
O4—S1—C9	108.12 (9)	C8—C7—H7	120.00
O5—S1—N1	108.56 (8)	C9—C8—H8	121.00
O5—S1—C9	109.51 (9)	C7—C8—H8	121.00
N1—S1—C9	102.07 (9)	N1—C10—H10B	109.00
O9—S2—O10	119.03 (3)	N1—C10—H10C	109.00
O9—S2—N2	107.87 (3)	N1—C10—H10A	109.00
O9—S2—C19	108.08 (7)	H10A—C10—H10B	109.00
O10—S2—N2	108.36 (3)	H10B—C10—H10C	109.00
O10—S2—C19	109.87 (7)	H10A—C10—H10C	109.00
N2—S2—C19	102.34 (7)	O6—C11—O7	123.53 (5)
C1—O1—H1	109.6 (17)	O6—C11—C12	115.45 (4)
C3—O3—H3	105.2 (16)	O7—C11—C12	121.03 (4)
C11—O6—H6A	108.00	N2—C12—C11	118.50 (3)
C13—O8—H8A	103.00	N2—C12—C13	120.77 (4)
H11A—O11—H11B	102 (3)	C11—C12—C13	120.72 (4)
S1—N1—C2	114.15 (12)	C12—C13—C14	123.01 (4)
S1—N1—C10	118.74 (10)	O8—C13—C12	123.29 (5)
C2—N1—C10	117.70 (13)	O8—C13—C14	113.69 (4)
S2—N2—C20	117.81 (9)	C13—C14—C15	121.33 (5)
S2—N2—C12	113.99 (3)	C13—C14—C19	120.41 (8)
C12—N2—C20	115.64 (10)	C15—C14—C19	118.23 (9)
O1—C1—O2	123.45 (18)	C14—C15—C16	120.03 (12)
O1—C1—C2	115.62 (15)	C15—C16—C17	120.9 (2)
O2—C1—C2	120.91 (18)	C16—C17—C18	120.6 (2)
N1—C2—C1	118.39 (16)	C17—C18—C19	118.7 (2)
C1—C2—C3	120.37 (16)	S2—C19—C14	117.15 (13)
N1—C2—C3	121.22 (16)	S2—C19—C18	121.23 (16)
O3—C3—C4	113.89 (16)	C14—C19—C18	121.47 (17)
O3—C3—C2	123.67 (16)	C16—C15—H15	120.00
C2—C3—C4	122.44 (16)	C14—C15—H15	120.00
C3—C4—C5	121.78 (17)	C15—C16—H16	120.00
C5—C4—C9	118.12 (18)	C17—C16—H16	120.00
C3—C4—C9	120.10 (16)	C18—C17—H17	120.00
C4—C5—C6	120.3 (2)	C16—C17—H17	120.00
C5—C6—C7	120.8 (2)	C17—C18—H18	121.00
C6—C7—C8	120.6 (2)	C19—C18—H18	121.00
C7—C8—C9	118.5 (2)	N2—C20—H20B	109.00
C4—C9—C8	121.72 (18)	N2—C20—H20C	109.00
S1—C9—C4	117.15 (14)	N2—C20—H20A	109.00
S1—C9—C8	121.07 (15)	H20A—C20—H20C	109.00
C6—C5—H5	120.00	H20B—C20—H20C	109.00
C4—C5—H5	120.00	H20A—C20—H20B	109.00
C5—C6—H6	120.00
O4—S1—N1—C2	−61.72 (14)	C1—C2—C3—C4	179.38 (19)
O4—S1—N1—C10	152.50 (10)	O3—C3—C4—C9	−158.93 (19)
O5—S1—N1—C2	167.65 (13)	C2—C3—C4—C5	−160.1 (2)
O5—S1—N1—C10	21.87 (13)	C2—C3—C4—C9	20.5 (3)
C9—S1—N1—C2	52.05 (14)	O3—C3—C4—C5	20.4 (3)
C9—S1—N1—C10	−93.72 (12)	C3—C4—C5—C6	−179.9 (2)
O4—S1—C9—C4	78.31 (18)	C3—C4—C9—S1	2.5 (3)
O4—S1—C9—C8	−99.01 (19)	C3—C4—C9—C8	179.8 (2)
O5—S1—C9—C4	−150.19 (16)	C9—C4—C5—C6	−0.6 (3)
O5—S1—C9—C8	32.5 (2)	C5—C4—C9—C8	0.4 (3)
N1—S1—C9—C4	−35.29 (18)	C5—C4—C9—S1	−176.86 (16)
N1—S1—C9—C8	147.39 (18)	C4—C5—C6—C7	0.6 (3)
C19—S2—N2—C12	52.04 (8)	C5—C6—C7—C8	−0.5 (3)
C19—S2—N2—C20	−88.35 (13)	C6—C7—C8—C9	0.3 (3)
O9—S2—C19—C14	78.38 (14)	C7—C8—C9—S1	176.90 (17)
O9—S2—C19—C18	−97.21 (18)	C7—C8—C9—C4	−0.3 (3)
O10—S2—C19—C14	−150.27 (11)	O6—C11—C12—N2	−2.89 (5)
O10—S2—C19—C18	34.1 (2)	O6—C11—C12—C13	175.85 (4)
N2—S2—C19—C14	−35.32 (15)	O7—C11—C12—N2	176.85 (4)
N2—S2—C19—C18	149.09 (17)	O7—C11—C12—C13	−4.41 (6)
O10—S2—N2—C20	27.70 (12)	N2—C12—C13—O8	−179.45 (4)
O9—S2—N2—C12	−61.81 (4)	N2—C12—C13—C14	2.10 (6)
O9—S2—N2—C20	157.80 (11)	C11—C12—C13—O8	1.84 (6)
O10—S2—N2—C12	168.08 (3)	C11—C12—C13—C14	−176.62 (3)
S1—N1—C2—C1	140.26 (16)	O8—C13—C14—C15	15.95 (5)
S1—N1—C2—C3	−38.4 (2)	O8—C13—C14—C19	−162.03 (11)
C10—N1—C2—C1	−73.6 (2)	C12—C13—C14—C15	−165.46 (4)
C10—N1—C2—C3	107.7 (2)	C12—C13—C14—C19	16.56 (11)
S2—N2—C12—C11	138.41 (3)	C13—C14—C15—C16	−179.53 (11)
C20—N2—C12—C11	−80.31 (11)	C19—C14—C15—C16	−1.51 (15)
C20—N2—C12—C13	100.95 (11)	C13—C14—C19—S2	4.25 (18)
S2—N2—C12—C13	−40.33 (5)	C13—C14—C19—C18	179.83 (15)
O1—C1—C2—N1	3.0 (3)	C15—C14—C19—S2	−173.79 (8)
O1—C1—C2—C3	−178.26 (19)	C15—C14—C19—C18	1.8 (2)
O2—C1—C2—N1	−178.13 (18)	C14—C15—C16—C17	0.2 (2)
O2—C1—C2—C3	0.6 (3)	C15—C16—C17—C18	0.9 (3)
N1—C2—C3—O3	177.46 (18)	C16—C17—C18—C19	−0.7 (3)
N1—C2—C3—C4	−2.0 (3)	C17—C18—C19—S2	174.68 (17)
C1—C2—C3—O3	−1.2 (3)	C17—C18—C19—C14	−0.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.83 (2)	1.82 (2)	2.647 (2)	177 (2)
O3—H3···O2	0.88 (2)	1.76 (2)	2.558 (2)	150 (2)
O6—H6A···O11ii	0.89	1.70	2.5881 (17)	170
O8—H8A···O7	0.88	1.75	2.5675 (8)	154
O11—H11A···O4iii	0.81 (3)	2.28 (3)	3.029 (2)	155 (3)
O11—H11B···O7iii	0.84 (3)	2.06 (3)	2.8508 (18)	158 (3)
C10—H10B···O1iv	0.96	2.50	3.3679 (16)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.83 (2)	1.82 (2)	2.647 (2)	177 (2)
O3—H3⋯O2	0.88 (2)	1.76 (2)	2.558 (2)	150 (2)
O6—H6A⋯O11ii	0.89	1.70	2.5881 (17)	170
O8—H8A⋯O7	0.88	1.75	2.5675 (8)	154
O11—H11A⋯O4iii	0.81 (3)	2.28 (3)	3.029 (2)	155 (3)
O11—H11B⋯O7iii	0.84 (3)	2.06 (3)	2.8508 (18)	158 (3)
C10—H10B⋯O1iv	0.96	2.50	3.3679 (16)	151

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