(1,3-Benzodioxol-5-ylmethyl)­ammonium 2-meth­oxy-5-[(1E)-3-oxo-3-phenyl­prop-1-en-1-yl]bezenesulfonate monohydrate

The reaction of a chalcone derivative and an aryl­methyl­amine yields the title organic salt, C₈H₁₀NO₂⁺·C₁₆H₁₃O₅S⁻·H₂O. The 1,3-dioxolane ring exhibits an envelope conformation. The C—C—C—C torsion angle of 16.7 (7)° between the 2-meth­oxy-5-vinyl­benzene­sulfonate unit and the phenyl ring indicates the non-planarity of the system. The polar heads of the anion and cation are connected by two bifurcated N—H...O hydrogen bonds. The water mol­ecule completes hydro­philic inter­actions by N—H...O hydrogen bonds with the cation and O—H...O bonds with the anion along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.045
• wR factor = 0.128
• Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.52 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O7
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           66.71
           From the CIF: _reflns_number_total               3968
           Count of symmetry unique reflns         2243
           Completeness (_total/calc)            176.91%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1725
           Fraction of Friedel pairs measured     0.769
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4-PC (Enraf–Nonius, 1993); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

1,3-Benzodioxol-5-ylmethaneammonium 2-methoxy-5-[(1E)-3-oxo-3-phenylprop-1-en-1-yl] bezenesulfonate monohydrate

Crystal data

C8H10NO2^+·C16H13O5S^−·H2O	F(000) = 1024
Mr = 487.51	Dx = 1.376 Mg m^−3
Orthorhombic, Pca21	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2ac	Cell parameters from 25 reflections
a = 11.631 (1) Å	θ = 9.4–22.2°
b = 24.686 (1) Å	µ = 1.66 mm^−1
c = 8.198 (1) Å	T = 299 K
V = 2353.8 (4) Å^3	Prism, colourless
Z = 4	0.60 × 0.15 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	3553 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 66.7°, θmin = 1.8°
ω/2θ scans	h = −13→13
Absorption correction: psi-scan (North et al., 1968)	k = −29→29
Tmin = 0.688, Tmax = 0.854	l = −8→9
4302 measured reflections	3 standard reflections every 120 min
3968 independent reflections	intensity decay: 0.5%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.045	w = 1/[σ^2(Fo^2) + (0.0917P)^2 + 0.2858P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.128	(Δ/σ)max = 0.014
S = 1.04	Δρmax = 0.31 e Å^−3
3968 reflections	Δρmin = −0.34 e Å^−3
324 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
7 restraints	Extinction coefficient: 0.0046 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1725 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.01 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.44846 (5)	0.38950 (3)	0.42068 (9)	0.03183 (19)
O1	0.3951 (2)	0.42551 (11)	0.3039 (3)	0.0595 (7)
O2	0.5054 (2)	0.41746 (10)	0.5528 (3)	0.0530 (6)
O3	0.36739 (18)	0.34942 (9)	0.4792 (3)	0.0446 (6)
O4	0.6497 (2)	0.43546 (8)	0.2636 (3)	0.0477 (6)
O5	0.7229 (3)	0.09731 (11)	−0.0383 (5)	0.0976 (14)
C1	0.5547 (2)	0.35342 (11)	0.3103 (3)	0.0297 (6)
C2	0.6450 (2)	0.38135 (11)	0.2353 (4)	0.0340 (6)
C3	0.7222 (3)	0.35323 (12)	0.1379 (4)	0.0421 (8)
H3	0.7827	0.3714	0.0879	0.050*
C4	0.7089 (3)	0.29794 (12)	0.1154 (4)	0.0429 (7)
H4	0.7598	0.2796	0.0474	0.051*
C5	0.6212 (2)	0.26907 (11)	0.1919 (4)	0.0363 (6)
C6	0.5452 (2)	0.29753 (11)	0.2899 (4)	0.0337 (6)
H6	0.4867	0.2790	0.3432	0.040*
C7	0.6068 (3)	0.21006 (12)	0.1704 (4)	0.0418 (7)
H7	0.5588	0.1923	0.2436	0.050*
C8	0.6563 (3)	0.18020 (14)	0.0557 (5)	0.0523 (9)
H8	0.6980	0.1984	−0.0242	0.063*
C9	0.6510 (4)	0.12080 (14)	0.0442 (5)	0.0589 (10)
C10	0.5635 (3)	0.08832 (13)	0.1352 (5)	0.0465 (8)
C11	0.5988 (4)	0.04129 (14)	0.2133 (6)	0.0628 (11)
H11	0.6761	0.0316	0.2118	0.075*
C12	0.5206 (5)	0.00891 (17)	0.2927 (7)	0.0747 (13)
H12	0.5456	−0.0222	0.3458	0.090*
C13	0.4070 (4)	0.02212 (17)	0.2943 (6)	0.0728 (12)
H13	0.3550	0.0000	0.3488	0.087*
C14	0.3686 (3)	0.06802 (17)	0.2158 (6)	0.0685 (12)
H14	0.2907	0.0764	0.2146	0.082*
C15	0.4476 (3)	0.10172 (14)	0.1381 (6)	0.0577 (10)
H15	0.4226	0.1334	0.0879	0.069*
C16	0.7367 (4)	0.46618 (14)	0.1813 (6)	0.0704 (13)
H16A	0.7239	0.4646	0.0657	0.106*
H16B	0.8109	0.4513	0.2062	0.106*
H16C	0.7335	0.5032	0.2169	0.106*
O6	0.0986 (3)	0.12902 (10)	0.1610 (4)	0.0718 (8)
O7	−0.0514 (3)	0.18545 (12)	0.0893 (4)	0.0777 (10)
N1	0.1430 (2)	0.37842 (12)	0.3369 (3)	0.0398 (6)
H11N	0.2141 (17)	0.3746 (14)	0.347 (5)	0.048*
H12N	0.124 (3)	0.4112 (9)	0.371 (5)	0.048*
H13N	0.120 (3)	0.3775 (14)	0.240 (3)	0.048*
C17	0.0857 (3)	0.33623 (14)	0.4374 (5)	0.0545 (9)
H17A	0.0050	0.3453	0.4491	0.065*
H17B	0.1198	0.3360	0.5453	0.065*
C18	0.0959 (3)	0.28091 (14)	0.3643 (4)	0.0463 (8)
C19	0.1855 (3)	0.24736 (14)	0.4052 (5)	0.0547 (9)
H19	0.2416	0.2600	0.4765	0.066*
C20	0.1952 (3)	0.19492 (15)	0.3431 (6)	0.0625 (10)
H20	0.2564	0.1725	0.3706	0.075*
C21	0.1102 (3)	0.17833 (13)	0.2402 (5)	0.0511 (8)
C22	0.0213 (3)	0.21135 (14)	0.1966 (5)	0.0509 (8)
C23	0.0111 (3)	0.26320 (15)	0.2576 (5)	0.0531 (9)
H23	−0.0501	0.2854	0.2284	0.064*
C24	−0.0136 (4)	0.12997 (16)	0.0945 (6)	0.0713 (12)
H24A	−0.0653	0.1087	0.1616	0.086*
H24B	−0.0132	0.1147	−0.0146	0.086*
O8	0.0498 (3)	0.46600 (11)	0.4897 (4)	0.0727 (9)
H81O	0.031 (4)	0.4986 (10)	0.482 (5)	0.087*
H82O	0.040 (4)	0.4564 (17)	0.588 (3)	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0320 (3)	0.0318 (3)	0.0317 (3)	−0.0001 (2)	0.0045 (3)	−0.0010 (3)
O1	0.0598 (15)	0.0638 (15)	0.0548 (16)	0.0277 (12)	0.0147 (13)	0.0215 (13)
O2	0.0501 (13)	0.0629 (14)	0.0461 (14)	−0.0092 (12)	0.0052 (11)	−0.0238 (13)
O3	0.0389 (11)	0.0411 (11)	0.0538 (14)	−0.0076 (9)	0.0119 (10)	−0.0027 (10)
O4	0.0529 (13)	0.0329 (10)	0.0573 (15)	−0.0122 (9)	0.0211 (11)	−0.0088 (10)
O5	0.105 (3)	0.0561 (15)	0.131 (4)	−0.0028 (16)	0.055 (3)	−0.0356 (19)
C1	0.0293 (13)	0.0314 (13)	0.0285 (15)	0.0007 (10)	−0.0001 (11)	−0.0006 (11)
C2	0.0356 (14)	0.0326 (13)	0.0337 (15)	−0.0057 (11)	0.0002 (11)	−0.0041 (12)
C3	0.0380 (16)	0.0436 (15)	0.045 (2)	−0.0078 (12)	0.0134 (13)	−0.0062 (14)
C4	0.0438 (16)	0.0409 (16)	0.0439 (18)	0.0038 (13)	0.0079 (14)	−0.0107 (14)
C5	0.0384 (13)	0.0339 (14)	0.0365 (16)	0.0004 (11)	−0.0013 (13)	−0.0036 (13)
C6	0.0357 (14)	0.0326 (14)	0.0328 (15)	−0.0032 (11)	−0.0016 (12)	0.0022 (12)
C7	0.0510 (17)	0.0307 (14)	0.0438 (18)	0.0017 (13)	0.0002 (15)	−0.0017 (13)
C8	0.066 (2)	0.0389 (17)	0.052 (2)	0.0009 (15)	0.0116 (18)	−0.0082 (15)
C9	0.066 (2)	0.0426 (19)	0.068 (3)	0.0042 (16)	0.008 (2)	−0.0209 (18)
C10	0.0553 (18)	0.0331 (15)	0.051 (2)	0.0041 (14)	−0.0077 (16)	−0.0114 (15)
C11	0.062 (2)	0.0434 (19)	0.083 (3)	0.0109 (17)	−0.020 (2)	−0.0061 (19)
C12	0.101 (3)	0.041 (2)	0.082 (3)	−0.004 (2)	−0.025 (3)	0.011 (2)
C13	0.090 (3)	0.053 (2)	0.075 (3)	−0.019 (2)	−0.008 (3)	0.003 (2)
C14	0.054 (2)	0.058 (2)	0.093 (3)	−0.0063 (17)	−0.003 (2)	−0.011 (2)
C15	0.064 (2)	0.0390 (17)	0.070 (3)	0.0084 (15)	−0.008 (2)	−0.0035 (17)
C16	0.079 (3)	0.0439 (16)	0.089 (3)	−0.025 (2)	0.036 (3)	−0.011 (2)
O6	0.0807 (19)	0.0474 (14)	0.087 (2)	0.0052 (14)	−0.0101 (18)	−0.0204 (15)
O7	0.090 (2)	0.0641 (17)	0.079 (2)	0.0040 (15)	−0.0351 (18)	−0.0178 (17)
N1	0.0415 (14)	0.0453 (14)	0.0325 (14)	−0.0046 (12)	−0.0064 (12)	0.0006 (12)
C17	0.0643 (19)	0.0482 (17)	0.051 (2)	−0.0060 (15)	0.019 (2)	−0.0041 (17)
C18	0.0538 (18)	0.0443 (17)	0.0406 (18)	−0.0045 (14)	0.0101 (15)	−0.0006 (14)
C19	0.0545 (18)	0.0481 (17)	0.062 (2)	−0.0063 (14)	−0.0082 (19)	0.0017 (18)
C20	0.055 (2)	0.0479 (19)	0.084 (3)	0.0078 (16)	−0.012 (2)	−0.001 (2)
C21	0.058 (2)	0.0390 (16)	0.057 (2)	−0.0023 (15)	0.0023 (18)	−0.0015 (15)
C22	0.059 (2)	0.0476 (18)	0.046 (2)	−0.0017 (15)	−0.0063 (17)	−0.0031 (16)
C23	0.0540 (19)	0.0503 (19)	0.055 (2)	0.0086 (15)	−0.0050 (17)	−0.0010 (18)
C24	0.087 (3)	0.057 (2)	0.070 (3)	−0.005 (2)	−0.012 (3)	−0.016 (2)
O8	0.118 (3)	0.0400 (13)	0.0597 (16)	0.0122 (15)	0.0112 (18)	0.0046 (12)

Geometric parameters (Å, º)

S1—O2	1.445 (3)	C14—C15	1.394 (6)
S1—O1	1.447 (3)	C14—H14	0.9300
S1—O3	1.449 (2)	C15—H15	0.9300
S1—C1	1.772 (3)	C16—H16A	0.9600
O4—C2	1.357 (3)	C16—H16B	0.9600
O4—C16	1.433 (4)	C16—H16C	0.9600
O5—C9	1.222 (5)	O6—C21	1.386 (4)
C1—C6	1.394 (4)	O6—C24	1.415 (5)
C1—C2	1.399 (4)	O7—C22	1.377 (5)
C2—C3	1.387 (4)	O7—C24	1.439 (5)
C3—C4	1.386 (4)	N1—C17	1.485 (5)
C3—H3	0.9300	N1—H11N	0.837 (18)
C4—C5	1.394 (4)	N1—H12N	0.884 (18)
C4—H4	0.9300	N1—H13N	0.841 (19)
C5—C6	1.386 (4)	C17—C18	1.496 (5)
C5—C7	1.477 (4)	C17—H17A	0.9700
C6—H6	0.9300	C17—H17B	0.9700
C7—C8	1.326 (5)	C18—C19	1.374 (5)
C7—H7	0.9300	C18—C23	1.388 (5)
C8—C9	1.471 (5)	C19—C20	1.395 (5)
C8—H8	0.9300	C19—H19	0.9300
C9—C10	1.495 (5)	C20—C21	1.362 (5)
C10—C11	1.388 (5)	C20—H20	0.9300
C10—C15	1.388 (5)	C21—C22	1.365 (5)
C11—C12	1.375 (6)	C22—C23	1.379 (5)
C11—H11	0.9300	C23—H23	0.9300
C12—C13	1.361 (7)	C24—H24A	0.9700
C12—H12	0.9300	C24—H24B	0.9700
C13—C14	1.378 (6)	O8—H81O	0.836 (19)
C13—H13	0.9300	O8—H82O	0.850 (19)
O2—S1—O1	113.52 (17)	C10—C15—C14	120.4 (4)
O2—S1—O3	112.11 (15)	C10—C15—H15	119.8
O1—S1—O3	111.07 (15)	C14—C15—H15	119.8
O2—S1—C1	107.66 (13)	O4—C16—H16A	109.5
O1—S1—C1	105.69 (14)	O4—C16—H16B	109.5
O3—S1—C1	106.25 (13)	H16A—C16—H16B	109.5
C2—O4—C16	117.9 (3)	O4—C16—H16C	109.5
C6—C1—C2	119.6 (3)	H16A—C16—H16C	109.5
C6—C1—S1	120.2 (2)	H16B—C16—H16C	109.5
C2—C1—S1	120.0 (2)	C21—O6—C24	104.9 (3)
O4—C2—C3	124.4 (3)	C22—O7—C24	103.6 (3)
O4—C2—C1	116.1 (3)	C17—N1—H11N	108 (3)
C3—C2—C1	119.5 (3)	C17—N1—H12N	111 (3)
C4—C3—C2	119.8 (3)	H11N—N1—H12N	108 (3)
C4—C3—H3	120.1	C17—N1—H13N	111 (3)
C2—C3—H3	120.1	H11N—N1—H13N	114 (4)
C3—C4—C5	121.7 (3)	H12N—N1—H13N	105 (4)
C3—C4—H4	119.2	N1—C17—C18	112.5 (3)
C5—C4—H4	119.2	N1—C17—H17A	109.1
C6—C5—C4	117.9 (3)	C18—C17—H17A	109.1
C6—C5—C7	119.8 (3)	N1—C17—H17B	109.1
C4—C5—C7	122.2 (3)	C18—C17—H17B	109.1
C5—C6—C1	121.4 (3)	H17A—C17—H17B	107.8
C5—C6—H6	119.3	C19—C18—C23	120.2 (3)
C1—C6—H6	119.3	C19—C18—C17	120.8 (3)
C8—C7—C5	125.7 (3)	C23—C18—C17	118.9 (3)
C8—C7—H7	117.1	C18—C19—C20	122.1 (4)
C5—C7—H7	117.1	C18—C19—H19	119.0
C7—C8—C9	125.5 (4)	C20—C19—H19	119.0
C7—C8—H8	117.2	C21—C20—C19	116.5 (3)
C9—C8—H8	117.2	C21—C20—H20	121.7
O5—C9—C8	118.7 (4)	C19—C20—H20	121.7
O5—C9—C10	119.2 (3)	C20—C21—C22	122.2 (3)
C8—C9—C10	122.1 (3)	C20—C21—O6	128.7 (3)
C11—C10—C15	118.6 (4)	C22—C21—O6	109.1 (3)
C11—C10—C9	118.5 (3)	C21—C22—O7	110.8 (3)
C15—C10—C9	122.8 (3)	C21—C22—C23	121.6 (3)
C12—C11—C10	120.6 (4)	O7—C22—C23	127.6 (3)
C12—C11—H11	119.7	C22—C23—C18	117.4 (3)
C10—C11—H11	119.7	C22—C23—H23	121.3
C13—C12—C11	120.5 (4)	C18—C23—H23	121.3
C13—C12—H12	119.8	O6—C24—O7	108.0 (3)
C11—C12—H12	119.8	O6—C24—H24A	110.1
C12—C13—C14	120.5 (4)	O7—C24—H24A	110.1
C12—C13—H13	119.7	O6—C24—H24B	110.1
C14—C13—H13	119.7	O7—C24—H24B	110.1
C13—C14—C15	119.4 (4)	H24A—C24—H24B	108.4
C13—C14—H14	120.3	H81O—O8—H82O	108 (3)
C15—C14—H14	120.3
O2—S1—C1—C6	122.8 (3)	C15—C10—C11—C12	−0.5 (6)
O1—S1—C1—C6	−115.5 (3)	C9—C10—C11—C12	−177.3 (4)
O3—S1—C1—C6	2.5 (3)	C10—C11—C12—C13	0.9 (7)
O2—S1—C1—C2	−60.8 (3)	C11—C12—C13—C14	0.3 (8)
O1—S1—C1—C2	60.8 (3)	C12—C13—C14—C15	−1.7 (7)
O3—S1—C1—C2	178.9 (2)	C11—C10—C15—C14	−1.0 (6)
C16—O4—C2—C3	3.2 (5)	C9—C10—C15—C14	175.7 (4)
C16—O4—C2—C1	−176.3 (3)	C13—C14—C15—C10	2.1 (7)
C6—C1—C2—O4	−178.7 (3)	N1—C17—C18—C19	91.6 (4)
S1—C1—C2—O4	4.9 (4)	N1—C17—C18—C23	−90.3 (4)
C6—C1—C2—C3	1.7 (4)	C23—C18—C19—C20	−0.2 (6)
S1—C1—C2—C3	−174.6 (2)	C17—C18—C19—C20	177.8 (4)
O4—C2—C3—C4	−179.2 (3)	C18—C19—C20—C21	−0.5 (6)
C1—C2—C3—C4	0.3 (5)	C19—C20—C21—C22	1.4 (6)
C2—C3—C4—C5	−1.8 (5)	C19—C20—C21—O6	179.6 (4)
C3—C4—C5—C6	1.2 (5)	C24—O6—C21—C20	169.9 (4)
C3—C4—C5—C7	−179.3 (3)	C24—O6—C21—C22	−11.7 (5)
C4—C5—C6—C1	0.8 (4)	C20—C21—C22—O7	178.8 (4)
C7—C5—C6—C1	−178.7 (3)	O6—C21—C22—O7	0.2 (5)
C2—C1—C6—C5	−2.3 (4)	C20—C21—C22—C23	−1.5 (6)
S1—C1—C6—C5	174.0 (2)	O6—C21—C22—C23	180.0 (4)
C6—C5—C7—C8	164.7 (3)	C24—O7—C22—C21	11.1 (5)
C4—C5—C7—C8	−14.7 (5)	C24—O7—C22—C23	−168.6 (4)
C5—C7—C8—C9	173.6 (4)	C21—C22—C23—C18	0.7 (6)
C7—C8—C9—O5	−160.9 (4)	O7—C22—C23—C18	−179.6 (4)
C7—C8—C9—C10	16.7 (7)	C19—C18—C23—C22	0.2 (6)
O5—C9—C10—C11	41.3 (6)	C17—C18—C23—C22	−178.0 (3)
C8—C9—C10—C11	−136.3 (4)	C21—O6—C24—O7	18.6 (5)
O5—C9—C10—C15	−135.4 (5)	C22—O7—C24—O6	−18.3 (5)
C8—C9—C10—C15	47.0 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O3	0.84 (2)	2.18 (2)	2.947 (4)	153 (4)
N1—H11N···O1	0.84 (2)	2.48 (3)	3.166 (4)	140 (3)
N1—H12N···O8	0.88 (2)	1.88 (2)	2.723 (4)	160 (4)
N1—H13N···O3^i	0.84 (2)	2.25 (2)	3.021 (4)	153 (3)
N1—H13N···O2^i	0.84 (2)	2.34 (3)	3.055 (4)	144 (3)
O8—H81O···O2^ii	0.84 (2)	2.17 (3)	2.968 (4)	159 (4)
O8—H82O···O1^iii	0.85 (2)	2.07 (3)	2.837 (4)	151 (5)

Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) x−1/2, −y+1, z; (iii) −x+1/2, y, z+1/2.