Structural characterization and photochromic behaviour of a novel compound based on a π-acidic naphthalene di­imide derivative and a double hydroxide-bridged dinuclear Al^III aqua ion cluster

Noncovalent inter­actions, such as π–π stacking inter­actions, C—H...π inter­actions and hydrogen bonding, are important driving forces for self-assembly in the construction of functional supermolecules and materials, especially in multicomponent supra­molecular systems. Herein, a novel compound based on a π-acidic naphthalene di­imide derivative and a double hydroxide-bridged dinuclear Al³⁺ aqua ion cluster, namely bis­[N,N′-bis­(2-sulfonato­eth­yl)-1,4,5,8-naphthalene di­imide] di-μ-hydroxido-bis­[tetra­aqua­aluminium(III)] tetra­hydrate, (C₁₈H₁₂N₂O₁₀S₂)₂[Al₂(OH)₂(H₂O)₈]·4H₂O, was obtained using the above-mentioned common noncovalent inter­actions, as well as uncommon lone-pair–π inter­actions. Functional mol­ecular modules were connected by these noncovalent inter­actions to generate obvious photochromic properties. The compound was prepared by the self-assembly of N,N′-bis­(2-sulfoeth­yl)-1,4,5,8-naphthalene di­imide and Al(NO₃)₃·9H₂O under mixed solvothermal conditions, and was characterized in detail by single-crystal X-ray diffraction, powder X-ray diffraction and FT–IR spectroscopy. The thermal stability and photochromic properties were also investigated; furthermore, in-situ solid-state UV–Vis absorption spectroscopy and electron spin resonance (ESR) were used to clarify the photochromic mechanism.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis[N,N'-bis(2-sulfonatoethyl)-1,4,5,8-naphthalene diimide] di-µ-hydroxido-bis[tetraaquaaluminium(III)] tetrahydrate

Crystal data

(C18H12N2O10S2)2[Al2(OH)2(H2O)8]·4H2O	Z = 1
Mr = 1265.00	F(000) = 656
Triclinic, P1	Dx = 1.724 Mg m^−3
a = 8.1442 (4) Å	Cu Kα radiation, λ = 1.54184 Å
b = 9.2736 (5) Å	Cell parameters from 2864 reflections
c = 17.1777 (10) Å	θ = 5.0–76.4°
α = 76.525 (5)°	µ = 3.17 mm^−1
β = 80.080 (4)°	T = 100 K
γ = 76.808 (4)°	Parallelepiped, yellow
V = 1218.60 (12) Å^3	0.3 × 0.2 × 0.08 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	4284 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	3439 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.058
Detector resolution: 10.3503 pixels mm^-1	θmax = 66.6°, θmin = 5.0°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −11→10
Tmin = 0.488, Tmax = 1.000	l = −20→20
7812 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.089P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4284 reflections	Δρmax = 0.56 e Å^−3
402 parameters	Δρmin = −0.74 e Å^−3
17 restraints

Special details

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. A suitable single crystal was mounted on a loop for the X-ray measurement. Diffraction data was collected on a SuperNova (Dual source) diffractometer equipped with the CrysAlis PRO X-ray crystallography data systems. The measurement was made by using graphic monochromatic Cu Kα radiation (λ = 1.54184 Å) at 100 K under a cold nitrogen stream. Using OLEX2 (Dolomanov et al., 2009.), the structure was solved with the SHELXT (Sheldrick, 2008) structure solution program using Intrinsic Phasing and refined with the SHELXL (Sheldrick, 2015) refinement package using least-squares minimisation. Crystallographic data has been deposited at the Cambridge Crystallographic Data Center with reference number CCDC 1868171. This data can be obtained free of charge from The Cambridge Crystallographic Data Centre via https://www.ccdc.cam.ac.uk/data_request/cif.

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

	x	y	z	Uiso*/Ueq
S1	0.26152 (9)	1.01210 (8)	0.13293 (4)	0.0157 (2)
Al1	0.05436 (11)	0.56602 (10)	0.05626 (5)	0.0152 (2)
N1	0.1635 (3)	0.7190 (3)	0.34171 (16)	0.0200 (6)
N2	0.2709 (3)	0.0781 (3)	0.65591 (15)	0.0161 (5)
O1	0.1119 (3)	1.0200 (3)	0.09428 (13)	0.0215 (5)
O2	0.4174 (3)	0.9912 (3)	0.07733 (13)	0.0212 (5)
O3	0.2434 (3)	1.1389 (2)	0.17279 (14)	0.0230 (5)
O4	0.0423 (3)	0.5925 (3)	0.27538 (13)	0.0229 (5)
O5	0.2971 (3)	0.8418 (3)	0.40449 (14)	0.0259 (5)
O6	0.1810 (3)	−0.0574 (2)	0.58274 (13)	0.0229 (5)
O7	0.3538 (3)	0.2132 (3)	0.73129 (13)	0.0213 (5)
O8	0.2821 (3)	−0.3876 (3)	0.76957 (13)	0.0196 (5)
O9	0.5866 (3)	−0.4405 (3)	0.77641 (13)	0.0208 (5)
O10	0.3912 (3)	−0.3015 (3)	0.87021 (12)	0.0191 (5)
O11	−0.1395 (3)	0.5648 (2)	0.01369 (13)	0.0163 (4)
O12	0.1074 (3)	0.7393 (3)	−0.02352 (13)	0.0179 (5)
H12A	0.039 (4)	0.816 (3)	−0.043 (2)	0.027*
H12B	0.188 (3)	0.725 (4)	−0.0608 (15)	0.027*
O13	−0.0633 (3)	0.6956 (3)	0.12526 (13)	0.0204 (5)
H13A	−0.051 (5)	0.674 (4)	0.1744 (8)	0.031*
H13B	−0.132 (4)	0.779 (2)	0.117 (2)	0.031*
O14	0.2682 (3)	0.5543 (3)	0.08894 (13)	0.0193 (5)
H14A	0.340 (4)	0.609 (4)	0.0649 (18)	0.029*
H14B	0.302 (4)	0.516 (4)	0.1341 (12)	0.029*
O15	0.0262 (3)	0.4062 (2)	0.14757 (13)	0.0184 (5)
H15A	−0.063 (3)	0.389 (4)	0.1768 (19)	0.028*
H15B	0.097 (3)	0.324 (2)	0.154 (2)	0.028*
O16	0.5096 (3)	0.7092 (2)	0.01376 (13)	0.0203 (5)
H16A	0.494389	0.797988	0.022835	0.030*
H16B	0.502259	0.714810	−0.035696	0.030*
O17	0.7624 (3)	0.9596 (2)	0.08111 (13)	0.0222 (5)
C1	0.2821 (4)	0.8453 (3)	0.20877 (18)	0.0164 (6)
H1A	0.285652	0.757420	0.184596	0.020*
H1B	0.390434	0.829838	0.231127	0.020*
C2	0.1352 (4)	0.8539 (4)	0.27660 (19)	0.0220 (7)
H2A	0.125485	0.946058	0.298176	0.026*
H2B	0.027509	0.860312	0.255449	0.026*
C3	0.1152 (4)	0.5892 (4)	0.33203 (18)	0.0190 (7)
C4	0.1538 (4)	0.4515 (4)	0.39480 (18)	0.0173 (6)
C5	0.2189 (4)	0.4589 (4)	0.46453 (18)	0.0163 (6)
C6	0.2603 (4)	0.5953 (4)	0.47315 (19)	0.0185 (6)
C7	0.2448 (4)	0.7284 (4)	0.40553 (19)	0.0208 (7)
C8	0.3137 (4)	0.6028 (4)	0.54356 (19)	0.0196 (7)
H8	0.338679	0.694748	0.549198	0.024*
C9	0.3318 (4)	0.4760 (4)	0.60741 (18)	0.0174 (6)
H9	0.367406	0.482897	0.656016	0.021*
C10	0.2973 (4)	0.3408 (4)	0.59909 (18)	0.0158 (6)
C11	0.2411 (4)	0.3308 (3)	0.52765 (18)	0.0156 (6)
C12	0.2019 (4)	0.1956 (4)	0.51850 (18)	0.0164 (6)
C13	0.1424 (4)	0.1878 (4)	0.44938 (19)	0.0205 (7)
H13	0.118773	0.095403	0.443560	0.025*
C14	0.1169 (4)	0.3176 (4)	0.38735 (19)	0.0208 (7)
H14	0.074036	0.312842	0.340149	0.025*
C15	0.2177 (4)	0.0612 (4)	0.58584 (18)	0.0181 (6)
C16	0.3123 (4)	0.2093 (4)	0.66716 (18)	0.0164 (6)
C17	0.2754 (4)	−0.0525 (4)	0.72472 (18)	0.0179 (6)
H17A	0.180420	−0.103456	0.725810	0.022*
H17B	0.259392	−0.015801	0.775735	0.022*
C18	0.4429 (4)	−0.1660 (4)	0.71914 (19)	0.0165 (6)
H11	−0.237 (3)	0.605 (4)	0.023 (2)	0.025*
H17C	0.659 (2)	0.961 (4)	0.086 (2)	0.025*
H17D	0.793 (4)	1.005 (4)	0.0360 (14)	0.025*
S2	0.42425 (9)	−0.33744 (8)	0.78929 (4)	0.0156 (2)
H18A	0.533 (5)	−0.137 (4)	0.734 (2)	0.018 (9)*
H18B	0.475 (5)	−0.197 (5)	0.667 (3)	0.033 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0164 (4)	0.0177 (4)	0.0105 (4)	−0.0054 (3)	−0.0007 (3)	0.0034 (3)
Al1	0.0179 (5)	0.0166 (5)	0.0105 (4)	−0.0057 (3)	−0.0025 (3)	0.0013 (4)
N1	0.0236 (14)	0.0199 (14)	0.0107 (13)	−0.0035 (11)	0.0024 (11)	0.0043 (11)
N2	0.0189 (13)	0.0162 (13)	0.0103 (12)	−0.0028 (10)	−0.0030 (10)	0.0035 (11)
O1	0.0200 (11)	0.0245 (12)	0.0178 (11)	−0.0067 (9)	−0.0060 (9)	0.0048 (10)
O2	0.0188 (11)	0.0269 (12)	0.0134 (11)	−0.0074 (9)	0.0036 (9)	0.0033 (10)
O3	0.0306 (13)	0.0172 (11)	0.0195 (12)	−0.0051 (9)	−0.0054 (10)	0.0012 (9)
O4	0.0244 (12)	0.0300 (13)	0.0109 (11)	−0.0032 (10)	−0.0036 (9)	0.0013 (10)
O5	0.0379 (14)	0.0170 (12)	0.0200 (12)	−0.0098 (10)	0.0008 (10)	0.0031 (10)
O6	0.0347 (13)	0.0185 (12)	0.0166 (11)	−0.0102 (10)	−0.0051 (10)	0.0008 (10)
O7	0.0280 (12)	0.0246 (12)	0.0110 (11)	−0.0078 (10)	−0.0057 (9)	0.0019 (9)
O8	0.0221 (11)	0.0228 (12)	0.0133 (11)	−0.0091 (9)	0.0004 (9)	−0.0001 (9)
O9	0.0206 (11)	0.0226 (12)	0.0136 (11)	0.0005 (9)	0.0005 (9)	0.0008 (9)
O10	0.0216 (11)	0.0239 (12)	0.0094 (10)	−0.0057 (9)	−0.0011 (8)	0.0017 (9)
O11	0.0146 (10)	0.0211 (11)	0.0137 (10)	−0.0051 (9)	−0.0004 (8)	−0.0037 (9)
O12	0.0208 (11)	0.0191 (11)	0.0108 (10)	−0.0043 (9)	−0.0012 (8)	0.0026 (9)
O13	0.0276 (12)	0.0204 (12)	0.0104 (10)	−0.0011 (9)	−0.0035 (9)	−0.0002 (9)
O14	0.0206 (11)	0.0239 (12)	0.0133 (11)	−0.0102 (9)	−0.0052 (9)	0.0047 (9)
O15	0.0197 (11)	0.0178 (11)	0.0146 (11)	−0.0063 (9)	−0.0004 (9)	0.0043 (9)
O16	0.0229 (11)	0.0215 (11)	0.0170 (11)	−0.0054 (9)	−0.0041 (9)	−0.0025 (10)
O17	0.0200 (11)	0.0266 (13)	0.0172 (12)	−0.0053 (10)	−0.0009 (9)	0.0009 (10)
C1	0.0203 (15)	0.0135 (14)	0.0101 (14)	−0.0027 (12)	−0.0002 (12)	0.0063 (12)
C2	0.0223 (16)	0.0226 (17)	0.0131 (15)	−0.0007 (13)	0.0026 (13)	0.0053 (14)
C3	0.0187 (15)	0.0235 (17)	0.0108 (15)	−0.0045 (13)	0.0027 (12)	0.0017 (13)
C4	0.0186 (15)	0.0209 (16)	0.0091 (14)	−0.0049 (12)	−0.0004 (12)	0.0036 (13)
C5	0.0189 (15)	0.0189 (15)	0.0096 (14)	−0.0070 (12)	−0.0002 (12)	0.0020 (13)
C6	0.0191 (15)	0.0182 (15)	0.0142 (15)	−0.0025 (12)	0.0017 (12)	0.0006 (13)
C7	0.0237 (16)	0.0216 (17)	0.0135 (15)	−0.0056 (13)	0.0038 (12)	0.0001 (14)
C8	0.0211 (16)	0.0181 (15)	0.0196 (16)	−0.0066 (12)	0.0018 (13)	−0.0040 (13)
C9	0.0196 (15)	0.0205 (16)	0.0126 (15)	−0.0043 (12)	−0.0009 (12)	−0.0046 (13)
C10	0.0148 (14)	0.0195 (16)	0.0106 (14)	−0.0051 (12)	0.0005 (11)	0.0021 (12)
C11	0.0160 (14)	0.0178 (15)	0.0113 (14)	−0.0041 (12)	−0.0009 (11)	0.0005 (12)
C12	0.0178 (15)	0.0193 (15)	0.0111 (14)	−0.0064 (12)	−0.0012 (11)	0.0009 (13)
C13	0.0223 (16)	0.0244 (17)	0.0156 (16)	−0.0072 (13)	−0.0032 (12)	−0.0024 (14)
C14	0.0239 (16)	0.0286 (18)	0.0106 (15)	−0.0073 (14)	−0.0033 (12)	−0.0023 (13)
C15	0.0211 (16)	0.0186 (16)	0.0128 (15)	−0.0029 (12)	−0.0010 (12)	−0.0014 (13)
C16	0.0150 (14)	0.0192 (15)	0.0140 (15)	−0.0059 (12)	−0.0012 (12)	0.0008 (13)
C17	0.0190 (15)	0.0196 (16)	0.0115 (14)	−0.0067 (12)	−0.0001 (12)	0.0056 (13)
C18	0.0166 (15)	0.0165 (15)	0.0139 (15)	−0.0051 (12)	−0.0011 (12)	0.0032 (13)
S2	0.0182 (4)	0.0171 (4)	0.0092 (4)	−0.0039 (3)	−0.0013 (3)	0.0020 (3)

Geometric parameters (Å, º)

S1—O1	1.465 (2)	O16—H16B	0.8510
S1—O2	1.451 (2)	O17—H17C	0.834 (18)
S1—O3	1.461 (2)	O17—H17D	0.821 (18)
S1—C1	1.770 (3)	C1—H1A	0.9900
Al1—Al1^i	2.8646 (18)	C1—H1B	0.9900
Al1—O11	1.855 (2)	C1—C2	1.521 (4)
Al1—O11^i	1.845 (2)	C2—H2A	0.9900
Al1—O12	1.932 (2)	C2—H2B	0.9900
Al1—O13	1.874 (2)	C3—C4	1.477 (4)
Al1—O14	1.893 (2)	C4—C5	1.413 (4)
Al1—O15	1.912 (2)	C4—C14	1.381 (5)
N1—C2	1.474 (4)	C5—C6	1.427 (4)
N1—C3	1.401 (4)	C5—C11	1.410 (4)
N1—C7	1.404 (4)	C6—C7	1.483 (4)
N2—C15	1.399 (4)	C6—C8	1.374 (5)
N2—C16	1.397 (4)	C8—H8	0.9500
N2—C17	1.481 (4)	C8—C9	1.409 (5)
O4—C3	1.216 (4)	C9—H9	0.9500
O5—C7	1.216 (4)	C9—C10	1.389 (4)
O6—C15	1.220 (4)	C10—C11	1.410 (4)
O7—C16	1.217 (4)	C10—C16	1.479 (4)
O8—S2	1.458 (2)	C11—C12	1.411 (4)
O9—S2	1.460 (2)	C12—C13	1.380 (4)
O10—S2	1.470 (2)	C12—C15	1.487 (4)
O11—H11	0.804 (19)	C13—H13	0.9500
O12—H12A	0.838 (10)	C13—C14	1.411 (5)
O12—H12B	0.843 (10)	C14—H14	0.9500
O13—H13A	0.838 (10)	C17—H17A	0.9900
O13—H13B	0.843 (10)	C17—H17B	0.9900
O14—H14A	0.849 (10)	C17—C18	1.524 (4)
O14—H14B	0.842 (10)	C18—S2	1.777 (3)
O15—H15A	0.835 (10)	C18—H18A	0.93 (4)
O15—H15B	0.841 (10)	C18—H18B	0.98 (4)
O16—H16A	0.8506
O1—S1—C1	107.48 (14)	H2A—C2—H2B	108.1
O2—S1—O1	110.80 (13)	N1—C3—C4	116.6 (3)
O2—S1—O3	113.80 (14)	O4—C3—N1	120.8 (3)
O2—S1—C1	104.82 (14)	O4—C3—C4	122.5 (3)
O3—S1—O1	112.33 (14)	C5—C4—C3	120.1 (3)
O3—S1—C1	107.06 (14)	C14—C4—C3	119.9 (3)
O11^i—Al1—Al1^i	39.38 (7)	C14—C4—C5	120.0 (3)
O11—Al1—Al1^i	39.13 (7)	C4—C5—C6	121.1 (3)
O11^i—Al1—O11	78.51 (11)	C11—C5—C4	120.0 (3)
O11^i—Al1—O12	92.95 (10)	C11—C5—C6	118.9 (3)
O11—Al1—O12	93.71 (10)	C5—C6—C7	119.3 (3)
O11—Al1—O13	93.43 (11)	C8—C6—C5	120.1 (3)
O11^i—Al1—O13	171.71 (11)	C8—C6—C7	120.6 (3)
O11^i—Al1—O14	94.18 (11)	N1—C7—C6	116.5 (3)
O11—Al1—O14	172.54 (11)	O5—C7—N1	120.5 (3)
O11—Al1—O15	96.20 (10)	O5—C7—C6	122.9 (3)
O11^i—Al1—O15	93.42 (11)	C6—C8—H8	119.6
O12—Al1—Al1^i	94.30 (8)	C6—C8—C9	120.9 (3)
O13—Al1—Al1^i	132.53 (9)	C9—C8—H8	119.6
O13—Al1—O12	89.45 (11)	C8—C9—H9	120.1
O13—Al1—O14	93.93 (11)	C10—C9—C8	119.8 (3)
O13—Al1—O15	85.48 (10)	C10—C9—H9	120.1
O14—Al1—Al1^i	133.54 (9)	C9—C10—C11	120.4 (3)
O14—Al1—O12	85.12 (10)	C9—C10—C16	119.4 (3)
O14—Al1—O15	85.63 (10)	C11—C10—C16	120.2 (3)
O15—Al1—Al1^i	96.22 (8)	C5—C11—C12	118.8 (3)
O15—Al1—O12	169.12 (11)	C10—C11—C5	119.9 (3)
C3—N1—C2	116.8 (3)	C10—C11—C12	121.4 (3)
C3—N1—C7	125.5 (3)	C11—C12—C15	119.4 (3)
C7—N1—C2	117.6 (3)	C13—C12—C11	121.1 (3)
C15—N2—C17	116.7 (3)	C13—C12—C15	119.4 (3)
C16—N2—C15	125.5 (3)	C12—C13—H13	120.2
C16—N2—C17	117.8 (2)	C12—C13—C14	119.7 (3)
Al1^i—O11—Al1	101.49 (11)	C14—C13—H13	120.2
Al1^i—O11—H11	127 (3)	C4—C14—C13	120.5 (3)
Al1—O11—H11	131 (3)	C4—C14—H14	119.7
Al1—O12—H12A	128 (2)	C13—C14—H14	119.7
Al1—O12—H12B	118 (2)	N2—C15—C12	116.9 (3)
H12A—O12—H12B	105 (2)	O6—C15—N2	120.3 (3)
Al1—O13—H13A	120 (2)	O6—C15—C12	122.7 (3)
Al1—O13—H13B	133 (2)	N2—C16—C10	116.6 (3)
H13A—O13—H13B	107 (2)	O7—C16—N2	120.3 (3)
Al1—O14—H14A	126 (2)	O7—C16—C10	123.0 (3)
Al1—O14—H14B	129 (2)	N2—C17—H17A	109.2
H14A—O14—H14B	104 (2)	N2—C17—H17B	109.2
Al1—O15—H15A	128 (2)	N2—C17—C18	111.8 (2)
Al1—O15—H15B	121 (2)	H17A—C17—H17B	107.9
H15A—O15—H15B	107 (2)	C18—C17—H17A	109.2
H16A—O16—H16B	109.3	C18—C17—H17B	109.2
H17C—O17—H17D	109 (3)	C17—C18—S2	109.8 (2)
S1—C1—H1A	109.3	C17—C18—H18A	114 (2)
S1—C1—H1B	109.3	C17—C18—H18B	114 (2)
H1A—C1—H1B	108.0	S2—C18—H18A	103 (2)
C2—C1—S1	111.6 (2)	S2—C18—H18B	104 (2)
C2—C1—H1A	109.3	H18A—C18—H18B	110 (3)
C2—C1—H1B	109.3	O8—S2—O9	113.01 (14)
N1—C2—C1	110.1 (3)	O8—S2—O10	112.30 (13)
N1—C2—H2A	109.6	O8—S2—C18	105.80 (14)
N1—C2—H2B	109.6	O9—S2—O10	112.56 (13)
C1—C2—H2A	109.6	O9—S2—C18	105.65 (14)
C1—C2—H2B	109.6	O10—S2—C18	106.85 (15)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12A···O1^ii	0.84 (1)	1.87 (1)	2.704 (3)	176 (4)
O12—H12B···O10^iii	0.84 (1)	1.87 (1)	2.699 (3)	169 (4)
O13—H13A···O4	0.84 (1)	1.94 (1)	2.747 (3)	163 (3)
O13—H13B···O17^iv	0.84 (1)	1.72 (9)	2.55 (8)	167 (5)
O14—H14A···O16	0.85 (1)	1.83 (1)	2.674 (3)	175 (4)
O14—H14B···O9^v	0.84 (1)	1.83 (1)	2.664 (3)	169 (3)
O14—H14B···S2^v	0.84 (1)	2.78 (2)	3.499 (2)	144 (3)
O15—H15A···O8^vi	0.84 (1)	1.86 (1)	2.686 (3)	169 (3)
O15—H15B···O3^vii	0.84 (1)	1.85 (1)	2.688 (3)	176 (3)
C1—H1B···O7^viii	0.99	2.21	3.194 (4)	174
O11—H11···O16^iv	0.81 (2)	2.08 (2)	2.866 (3)	163 (4)
O17—H17C···O2	0.83 (2)	1.95 (2)	2.768 (3)	169 (3)
O17—H17D···O1^ix	0.82 (2)	2.29 (3)	2.987 (3)	144 (4)

Symmetry codes: (ii) −x, −y+2, −z; (iii) x, y+1, z−1; (iv) x−1, y, z; (v) −x+1, −y, −z+1; (vi) −x, −y, −z+1; (vii) x, y−1, z; (viii) −x+1, −y+1, −z+1; (ix) −x+1, −y+2, −z.