{6,6'-Dimeth-oxy-2,2'-[2,2-dimethyl-propane-1,3-diylbis(nitrilo-methyl-idyne)]diphenolato}nickel(II) 1.78-hydrate.

In the title complex, [Ni(C(21)H(24)N(2)O(4))]·1.78H(2)O, the Ni(II) ion has a slightly distorted planar geometry, coordinated by the two N and two O atoms of the tetra-dentate Schiff base ligand, with a mean deviation of 0.272 Å from the NiN(2)O(2) plane. The N and O donor atoms are mutually cis. The dihedral angle between two benzene rings of the ligand is 38.86 (8)°. There are also three solvent water mol-ecules, two of which lie across different crystallographic twofold rotation axes; one of these is partially occupied with a refined occupancy factor of 0.570 (7). The water mol-ecules are linked together as tetra-mers in R(2) (2)(8) ring motifs, which also connect two neighbouring mol-ecules of the complex through a network of O-H⋯O hydrogen bonds. The crystal structure is further stabilized by inter-molecular C-H⋯O and C-H⋯π inter-actions, which link neighbouring mol-ecules into extended chains along the b axis. Other inter-esting features of the crystal structure are the short inter-molecular C⋯C [3.204 (3)-3.365 (3) Å] and the C⋯O [3.199 (2)-3.205 (2) Å] contacts which are shorter than the sum of the van der Waals radii of these atoms.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Clark et al. (1968 ▶, 1969 ▶, 1970 ▶). For applications and bioactivity of Schiff base complexes, see: Elmali et al. (2000 ▶); Blower (1998 ▶); Granovski et al. (1993 ▶); Li & Chang (1991 ▶); Shahrokhian et al. (2000 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Ni(C21H24N2O4)]·1.78H2O

M = 459.29

Monoclinic,

a = 23.2513 (6) Å

b = 9.2709 (2) Å

c = 20.8024 (5) Å

β = 111.291 (1)°

V = 4178.12 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.97 mm−1

T = 100 K

0.48 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.655, T max = 0.959

19991 measured reflections

6519 independent reflections

4609 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.098

S = 1.06

6519 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014500/sj2621sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014500/sj2621Isup2.hkl

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

[Ni(C21H24N2O4)]·1.78H2O	F(000) = 1935
Mr = 459.29	Dx = 1.460 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5799 reflections
a = 23.2513 (6) Å	θ = 2.4–30.9°
b = 9.2709 (2) Å	µ = 0.97 mm−1
c = 20.8024 (5) Å	T = 100 K
β = 111.291 (1)°	Needle, green
V = 4178.12 (17) Å3	0.48 × 0.06 × 0.04 mm
Z = 8

Bruker SMART APEXII CCD area-detector diffractometer	6519 independent reflections
Radiation source: fine-focus sealed tube	4609 reflections with I > 2σ(I)
graphite	Rint = 0.040
φ and ω scans	θmax = 30.9°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −33→30
Tmin = 0.655, Tmax = 0.959	k = −13→13
19991 measured reflections	l = −30→30

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0393P)2 + 1.0555P] where P = (Fo2 + 2Fc2)/3
6519 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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. 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 > 2sigma(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	Occ. (<1)
Ni1	0.236534 (10)	0.03020 (3)	0.016967 (11)	0.01197 (8)
O1	0.20185 (6)	−0.04173 (15)	−0.07256 (6)	0.0141 (3)
O2	0.15706 (6)	0.08978 (16)	0.00363 (6)	0.0146 (3)
O3	0.15150 (6)	−0.03871 (16)	−0.20732 (7)	0.0198 (3)
O4	0.03874 (6)	0.13066 (18)	−0.03278 (7)	0.0263 (4)
N1	0.30718 (7)	−0.08539 (19)	0.04015 (7)	0.0126 (3)
N2	0.27481 (7)	0.15663 (19)	0.09066 (7)	0.0131 (3)
C1	0.23268 (8)	−0.1077 (2)	−0.10589 (9)	0.0128 (4)
C2	0.20584 (8)	−0.1127 (2)	−0.17960 (9)	0.0143 (4)
C3	0.23389 (9)	−0.1867 (2)	−0.21739 (10)	0.0184 (4)
H3A	0.2162	−0.1864	−0.2653	0.022*
C4	0.28894 (9)	−0.2625 (3)	−0.18454 (10)	0.0215 (5)
H4A	0.3070	−0.3147	−0.2104	0.026*
C5	0.31593 (9)	−0.2592 (2)	−0.11392 (10)	0.0191 (5)
H5A	0.3520	−0.3111	−0.0920	0.023*
C6	0.28970 (8)	−0.1783 (2)	−0.07416 (9)	0.0139 (4)
C7	0.32108 (8)	−0.1720 (2)	−0.00063 (9)	0.0149 (4)
H7A	0.3539	−0.2351	0.0191	0.018*
C8	0.34214 (8)	−0.0980 (2)	0.11514 (9)	0.0143 (4)
H8A	0.3701	−0.1794	0.1235	0.017*
H8B	0.3135	−0.1169	0.1384	0.017*
C9	0.37932 (8)	0.0387 (2)	0.14565 (9)	0.0145 (4)
C10	0.34240 (8)	0.1725 (2)	0.11110 (9)	0.0151 (4)
H10A	0.3559	0.2534	0.1426	0.018*
H10B	0.3517	0.1951	0.0704	0.018*
C11	0.24663 (8)	0.2501 (2)	0.11465 (9)	0.0136 (4)
H11A	0.2713	0.3124	0.1484	0.016*
C12	0.18108 (8)	0.2677 (2)	0.09453 (9)	0.0137 (4)
C13	0.15822 (9)	0.3744 (2)	0.12736 (9)	0.0165 (4)
H13A	0.1857	0.4290	0.1627	0.020*
C14	0.09596 (9)	0.3987 (2)	0.10780 (10)	0.0185 (4)
H14A	0.0815	0.4692	0.1299	0.022*
C15	0.05432 (9)	0.3170 (2)	0.05440 (10)	0.0197 (5)
H15A	0.0121	0.3326	0.0415	0.024*
C16	0.07557 (9)	0.2138 (2)	0.02094 (10)	0.0176 (4)
C17	0.14009 (8)	0.1858 (2)	0.03968 (9)	0.0140 (4)
C18	0.44051 (8)	0.0392 (3)	0.13346 (11)	0.0207 (5)
H18A	0.4323	0.0397	0.0848	0.031*
H18B	0.4638	−0.0454	0.1538	0.031*
H18C	0.4637	0.1237	0.1542	0.031*
C19	0.39200 (9)	0.0387 (3)	0.22342 (10)	0.0212 (5)
H19A	0.4149	0.1235	0.2440	0.032*
H19B	0.4155	−0.0455	0.2441	0.032*
H19C	0.3535	0.0379	0.2307	0.032*
C20	0.11522 (10)	−0.0671 (3)	−0.27807 (10)	0.0265 (5)
H20A	0.0770	−0.0152	−0.2908	0.040*
H20B	0.1069	−0.1686	−0.2843	0.040*
H20C	0.1374	−0.0365	−0.3066	0.040*
C21	−0.02618 (9)	0.1585 (3)	−0.05688 (11)	0.0341 (6)
H21A	−0.0470	0.0964	−0.0952	0.051*
H21B	−0.0338	0.2573	−0.0712	0.051*
H21C	−0.0413	0.1404	−0.0204	0.051*
O1W	0.0000	0.1551 (3)	−0.2500	0.0449 (7)
H1W1	−0.0179	0.1045	−0.2849	0.067*
O2W	0.06628 (7)	−0.03162 (18)	−0.13412 (8)	0.0316 (4)
H1W2	0.0657	−0.0153	−0.0937	0.047*
H2W2	0.1022	−0.0323	−0.1371	0.047*
O3W	0.0000	−0.2322 (4)	−0.2500	0.0320 (14)	0.570 (7)
H1W3	−0.0239	−0.1811	−0.2860	0.048*	0.570 (7)

	U11	U22	U33	U12	U13	U23
Ni1	0.01173 (11)	0.01265 (14)	0.01018 (11)	0.00058 (11)	0.00237 (8)	−0.00026 (11)
O1	0.0139 (6)	0.0158 (8)	0.0120 (6)	0.0011 (6)	0.0038 (5)	−0.0010 (6)
O2	0.0139 (6)	0.0159 (8)	0.0136 (6)	0.0012 (6)	0.0046 (5)	−0.0023 (6)
O3	0.0219 (7)	0.0210 (9)	0.0112 (6)	0.0054 (7)	−0.0001 (5)	−0.0023 (6)
O4	0.0119 (6)	0.0375 (10)	0.0256 (7)	0.0012 (7)	0.0020 (6)	−0.0132 (8)
N1	0.0132 (7)	0.0132 (9)	0.0104 (7)	−0.0018 (7)	0.0029 (6)	0.0011 (7)
N2	0.0137 (7)	0.0136 (9)	0.0105 (7)	−0.0004 (7)	0.0026 (6)	0.0029 (7)
C1	0.0146 (8)	0.0109 (10)	0.0133 (8)	−0.0031 (8)	0.0057 (7)	0.0002 (8)
C2	0.0155 (8)	0.0113 (11)	0.0150 (8)	−0.0020 (8)	0.0042 (7)	0.0000 (8)
C3	0.0231 (10)	0.0193 (12)	0.0135 (9)	−0.0021 (9)	0.0073 (8)	−0.0020 (9)
C4	0.0229 (10)	0.0242 (13)	0.0209 (10)	−0.0005 (10)	0.0123 (8)	−0.0073 (10)
C5	0.0144 (9)	0.0224 (13)	0.0210 (10)	0.0031 (9)	0.0070 (8)	−0.0004 (10)
C6	0.0142 (8)	0.0127 (10)	0.0150 (8)	−0.0030 (8)	0.0055 (7)	−0.0010 (8)
C7	0.0120 (8)	0.0144 (11)	0.0173 (9)	−0.0009 (8)	0.0042 (7)	0.0008 (9)
C8	0.0145 (8)	0.0146 (11)	0.0116 (8)	0.0000 (8)	0.0023 (7)	0.0028 (8)
C9	0.0140 (8)	0.0145 (11)	0.0132 (8)	−0.0025 (8)	0.0029 (7)	0.0002 (8)
C10	0.0146 (8)	0.0150 (11)	0.0161 (9)	−0.0028 (8)	0.0059 (7)	0.0012 (9)
C11	0.0183 (9)	0.0116 (11)	0.0101 (8)	−0.0026 (8)	0.0044 (7)	0.0020 (8)
C12	0.0175 (9)	0.0120 (11)	0.0129 (8)	0.0001 (8)	0.0071 (7)	0.0030 (8)
C13	0.0226 (9)	0.0129 (11)	0.0149 (9)	−0.0025 (9)	0.0078 (7)	0.0007 (8)
C14	0.0240 (10)	0.0166 (12)	0.0174 (9)	0.0038 (9)	0.0104 (8)	0.0009 (9)
C15	0.0156 (9)	0.0258 (13)	0.0188 (9)	0.0040 (9)	0.0076 (7)	0.0013 (10)
C16	0.0169 (9)	0.0205 (12)	0.0142 (9)	0.0008 (9)	0.0043 (7)	0.0004 (9)
C17	0.0164 (8)	0.0131 (11)	0.0131 (8)	0.0020 (8)	0.0061 (7)	0.0043 (8)
C18	0.0137 (8)	0.0220 (12)	0.0249 (10)	−0.0019 (9)	0.0052 (8)	0.0020 (10)
C19	0.0222 (10)	0.0235 (13)	0.0149 (9)	−0.0025 (10)	0.0033 (7)	−0.0007 (9)
C20	0.0263 (11)	0.0322 (15)	0.0139 (9)	0.0054 (11)	−0.0012 (8)	−0.0034 (10)
C21	0.0135 (9)	0.0545 (18)	0.0291 (11)	0.0012 (11)	0.0016 (8)	−0.0149 (13)
O1W	0.0409 (14)	0.0342 (16)	0.0516 (16)	0.000	0.0072 (12)	0.000
O2W	0.0210 (7)	0.0427 (11)	0.0294 (8)	−0.0017 (8)	0.0073 (6)	−0.0150 (8)
O3W	0.031 (2)	0.023 (3)	0.038 (2)	0.000	0.0070 (18)	0.000

Ni1—O2	1.8505 (13)	C9—C19	1.535 (3)
Ni1—O1	1.8636 (13)	C10—H10A	0.9700
Ni1—N1	1.8719 (16)	C10—H10B	0.9700
Ni1—N2	1.8776 (16)	C11—C12	1.436 (2)
O1—C1	1.315 (2)	C11—H11A	0.9300
O2—C17	1.313 (2)	C12—C13	1.411 (3)
O3—C2	1.368 (2)	C12—C17	1.413 (3)
O3—C20	1.430 (2)	C13—C14	1.373 (3)
O4—C16	1.372 (2)	C13—H13A	0.9300
O4—C21	1.431 (2)	C14—C15	1.402 (3)
N1—C7	1.292 (2)	C14—H14A	0.9300
N1—C8	1.479 (2)	C15—C16	1.376 (3)
N2—C11	1.291 (2)	C15—H15A	0.9300
N2—C10	1.479 (2)	C16—C17	1.430 (2)
C1—C6	1.409 (3)	C18—H18A	0.9600
C1—C2	1.431 (2)	C18—H18B	0.9600
C2—C3	1.373 (3)	C18—H18C	0.9600
C3—C4	1.402 (3)	C19—H19A	0.9600
C3—H3A	0.9300	C19—H19B	0.9600
C4—C5	1.372 (3)	C19—H19C	0.9600
C4—H4A	0.9300	C20—H20A	0.9600
C5—C6	1.409 (3)	C20—H20B	0.9600
C5—H5A	0.9300	C20—H20C	0.9600
C6—C7	1.437 (2)	C21—H21A	0.9600
C7—H7A	0.9300	C21—H21B	0.9600
C8—C9	1.536 (3)	C21—H21C	0.9600
C8—H8A	0.9700	O1W—H1W1	0.8368
C8—H8B	0.9700	O2W—H1W2	0.8598
C9—C10	1.531 (3)	O2W—H2W2	0.8602
C9—C18	1.533 (3)	O3W—H1W3	0.8900
O2—Ni1—O1	84.88 (5)	C9—C10—H10A	108.7
O2—Ni1—N1	160.84 (7)	N2—C10—H10B	108.7
O1—Ni1—N1	94.21 (6)	C9—C10—H10B	108.7
O2—Ni1—N2	95.02 (6)	H10A—C10—H10B	107.6
O1—Ni1—N2	160.77 (7)	N2—C11—C12	126.70 (18)
N1—Ni1—N2	92.04 (7)	N2—C11—H11A	116.7
C1—O1—Ni1	124.91 (11)	C12—C11—H11A	116.7
C17—O2—Ni1	127.39 (12)	C13—C12—C17	120.35 (17)
C2—O3—C20	116.80 (15)	C13—C12—C11	119.01 (18)
C16—O4—C21	116.83 (17)	C17—C12—C11	120.51 (17)
C7—N1—C8	118.09 (16)	C14—C13—C12	120.92 (18)
C7—N1—Ni1	126.32 (13)	C14—C13—H13A	119.5
C8—N1—Ni1	114.32 (12)	C12—C13—H13A	119.5
C11—N2—C10	117.23 (16)	C13—C14—C15	119.78 (19)
C11—N2—Ni1	125.31 (13)	C13—C14—H14A	120.1
C10—N2—Ni1	115.85 (12)	C15—C14—H14A	120.1
O1—C1—C6	124.71 (16)	C16—C15—C14	120.34 (18)
O1—C1—C2	118.08 (16)	C16—C15—H15A	119.8
C6—C1—C2	117.18 (17)	C14—C15—H15A	119.8
O3—C2—C3	124.56 (17)	O4—C16—C15	124.75 (17)
O3—C2—C1	114.34 (16)	O4—C16—C17	113.76 (17)
C3—C2—C1	121.10 (18)	C15—C16—C17	121.48 (18)
C2—C3—C4	120.73 (18)	O2—C17—C12	124.81 (17)
C2—C3—H3A	119.6	O2—C17—C16	118.05 (17)
C4—C3—H3A	119.6	C12—C17—C16	117.11 (18)
C5—C4—C3	119.49 (18)	C9—C18—H18A	109.5
C5—C4—H4A	120.3	C9—C18—H18B	109.5
C3—C4—H4A	120.3	H18A—C18—H18B	109.5
C4—C5—C6	120.88 (18)	C9—C18—H18C	109.5
C4—C5—H5A	119.6	H18A—C18—H18C	109.5
C6—C5—H5A	119.6	H18B—C18—H18C	109.5
C5—C6—C1	120.43 (17)	C9—C19—H19A	109.5
C5—C6—C7	119.07 (17)	C9—C19—H19B	109.5
C1—C6—C7	120.48 (17)	H19A—C19—H19B	109.5
N1—C7—C6	124.96 (18)	C9—C19—H19C	109.5
N1—C7—H7A	117.5	H19A—C19—H19C	109.5
C6—C7—H7A	117.5	H19B—C19—H19C	109.5
N1—C8—C9	112.44 (16)	O3—C20—H20A	109.5
N1—C8—H8A	109.1	O3—C20—H20B	109.5
C9—C8—H8A	109.1	H20A—C20—H20B	109.5
N1—C8—H8B	109.1	O3—C20—H20C	109.5
C9—C8—H8B	109.1	H20A—C20—H20C	109.5
H8A—C8—H8B	107.8	H20B—C20—H20C	109.5
C10—C9—C18	108.41 (16)	O4—C21—H21A	109.5
C10—C9—C19	110.81 (16)	O4—C21—H21B	109.5
C18—C9—C19	109.85 (15)	H21A—C21—H21B	109.5
C10—C9—C8	109.82 (15)	O4—C21—H21C	109.5
C18—C9—C8	110.55 (17)	H21A—C21—H21C	109.5
C19—C9—C8	107.40 (16)	H21B—C21—H21C	109.5
N2—C10—C9	114.23 (16)	H1W2—O2W—H2W2	115.6
N2—C10—H10A	108.7
O2—Ni1—O1—C1	179.08 (15)	C8—N1—C7—C6	176.88 (17)
N1—Ni1—O1—C1	−20.13 (16)	Ni1—N1—C7—C6	10.6 (3)
N2—Ni1—O1—C1	88.5 (2)	C5—C6—C7—N1	168.97 (19)
O1—Ni1—O2—C17	−162.95 (16)	C1—C6—C7—N1	−12.7 (3)
N1—Ni1—O2—C17	109.0 (2)	C7—N1—C8—C9	116.78 (19)
N2—Ni1—O2—C17	−2.25 (16)	Ni1—N1—C8—C9	−75.31 (16)
O2—Ni1—N1—C7	90.5 (2)	N1—C8—C9—C10	37.6 (2)
O1—Ni1—N1—C7	3.93 (17)	N1—C8—C9—C18	−81.95 (19)
N2—Ni1—N1—C7	−157.87 (17)	N1—C8—C9—C19	158.22 (15)
O2—Ni1—N1—C8	−76.3 (2)	C11—N2—C10—C9	123.82 (18)
O1—Ni1—N1—C8	−162.81 (13)	Ni1—N2—C10—C9	−69.85 (17)
N2—Ni1—N1—C8	35.38 (13)	C18—C9—C10—N2	153.78 (16)
O2—Ni1—N2—C11	−2.15 (16)	C19—C9—C10—N2	−85.59 (19)
O1—Ni1—N2—C11	86.7 (2)	C8—C9—C10—N2	32.9 (2)
N1—Ni1—N2—C11	−164.32 (16)	C10—N2—C11—C12	170.83 (17)
O2—Ni1—N2—C10	−167.23 (13)	Ni1—N2—C11—C12	5.9 (3)
O1—Ni1—N2—C10	−78.4 (2)	N2—C11—C12—C13	178.81 (18)
N1—Ni1—N2—C10	30.60 (13)	N2—C11—C12—C17	−5.2 (3)
Ni1—O1—C1—C6	23.2 (3)	C17—C12—C13—C14	1.4 (3)
Ni1—O1—C1—C2	−158.92 (14)	C11—C12—C13—C14	177.37 (18)
C20—O3—C2—C3	14.6 (3)	C12—C13—C14—C15	−0.2 (3)
C20—O3—C2—C1	−165.57 (18)	C13—C14—C15—C16	−0.8 (3)
O1—C1—C2—O3	3.8 (3)	C21—O4—C16—C15	2.5 (3)
C6—C1—C2—O3	−178.18 (17)	C21—O4—C16—C17	−176.59 (19)
O1—C1—C2—C3	−176.36 (18)	C14—C15—C16—O4	−178.51 (19)
C6—C1—C2—C3	1.7 (3)	C14—C15—C16—C17	0.6 (3)
O3—C2—C3—C4	−178.48 (19)	Ni1—O2—C17—C12	3.2 (3)
C1—C2—C3—C4	1.6 (3)	Ni1—O2—C17—C16	−178.97 (13)
C2—C3—C4—C5	−1.9 (3)	C13—C12—C17—O2	176.22 (18)
C3—C4—C5—C6	−1.3 (3)	C11—C12—C17—O2	0.3 (3)
C4—C5—C6—C1	4.7 (3)	C13—C12—C17—C16	−1.6 (3)
C4—C5—C6—C7	−176.9 (2)	C11—C12—C17—C16	−177.50 (18)
O1—C1—C6—C5	173.11 (18)	O4—C16—C17—O2	1.8 (3)
C2—C1—C6—C5	−4.8 (3)	C15—C16—C17—O2	−177.33 (18)
O1—C1—C6—C7	−5.2 (3)	O4—C16—C17—C12	179.80 (17)
C2—C1—C6—C7	176.85 (18)	C15—C16—C17—C12	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2Wi	0.84	2.08	2.913 (2)	175
O2W—H1W2···O2	0.86	2.54	3.089 (2)	123
O2W—H1W2···O4	0.86	2.10	2.846 (2)	145
O2W—H2W2···O1	0.86	2.22	2.942 (2)	142
O2W—H2W2···O3	0.86	2.16	2.905 (2)	145
O3W—H1W3···O2Wi	0.89	2.11	2.991 (3)	169
C10—H10B···O2ii	0.97	2.48	3.251 (2)	136
C8—H8B···Cg1iii	0.97	2.57	3.370 (2)	139
C13—H13A···Cg1ii	0.93	2.75	3.377 (2)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2Wi	0.84	2.08	2.913 (2)	175
O2W—H1W2⋯O2	0.86	2.54	3.089 (2)	123
O2W—H1W2⋯O4	0.86	2.10	2.846 (2)	145
O2W—H2W2⋯O1	0.86	2.22	2.942 (2)	142
O2W—H2W2⋯O3	0.86	2.16	2.905 (2)	145
O3W—H1W3⋯O2Wi	0.89	2.11	2.991 (3)	169
C10—H10B⋯O2ii	0.97	2.48	3.251 (2)	136
C8—H8B⋯Cg1iii	0.97	2.57	3.370 (2)	139
C13—H13A⋯Cg1ii	0.93	2.75	3.377 (2)	125

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.