1-Methyl-2-[(E)-2,4,5-trimeth-oxy-styr-yl]pyridinium 4-meth-oxy-benzene-sulfonate monohydrate.

In the title compound, C(17)H(20)NO(3) (+)·C(7)H(7)O(4)S(-)·H(2)O, the cation exists in an E configuration with respect to the C=C bond and is twisted with a dihedral angle of 17.81 (8)° between the pyridinium and benzene rings. The benzene ring of the anion is almost parallel to the pyridinium ring [dihedral angle = 3.45 (9)°], whereas it is inclined to the benzene ring of the cation [dihedral angle = 17.62 (8)°]. The crystal structure is stabilized by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions which link the cations, anions and water mol-ecules into chains along the a axis. π-π inter-actions with centroid-centroid distances of 3.7751 (9) and 3.7920 (11) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to the non-linear optical properties and applications of pyridinium and quinolinium derivatives, see: Chanawanno et al. (2010 ▶), Chantrapromma et al. (2010 ▶); Fun et al. (2009 ▶); Ruanwas et al. (2010 ▶); Williams (1984 ▶). For related structures, see, Chantrapromma et al. (2007 ▶); Mueangkeaw et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C17H20NO3 +·C7H7O4S−·H2O

M = 491.55

Triclinic,

a = 6.8463 (4) Å

b = 10.8855 (5) Å

c = 15.8137 (8) Å

α = 83.950 (2)°

β = 81.355 (2)°

γ = 81.140 (2)°

V = 1147.14 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.19 mm−1

T = 100 K

0.40 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.927, T max = 0.989

20386 measured reflections

5219 independent reflections

4534 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.124

S = 1.05

5219 reflections

320 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.56 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/S1600536811008610/rz2563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008610/rz2563Isup2.hkl

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

C17H20NO3+·C7H7O4S−·H2O	Z = 2
Mr = 491.55	F(000) = 520
Triclinic, P1	Dx = 1.423 Mg m−3
Hall symbol: -P 1	Melting point = 453–454 K
a = 6.8463 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8855 (5) Å	Cell parameters from 5219 reflections
c = 15.8137 (8) Å	θ = 1.9–27.5°
α = 83.950 (2)°	µ = 0.19 mm−1
β = 81.355 (2)°	T = 100 K
γ = 81.140 (2)°	Needle, orange
V = 1147.14 (10) Å3	0.40 × 0.08 × 0.06 mm

Bruker APEXII CCD area-detector diffractometer	5219 independent reflections
Radiation source: sealed tube	4534 reflections with I > 2σ(I)
graphite	Rint = 0.044
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.927, Tmax = 0.989	k = −14→14
20386 measured reflections	l = −20→20

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) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.7052P] where P = (Fo2 + 2Fc2)/3
5219 reflections	(Δ/σ)max = 0.001
320 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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
O1	0.66045 (19)	0.25805 (10)	0.59540 (7)	0.0188 (3)
O2	0.68611 (19)	0.08432 (10)	0.71952 (7)	0.0175 (3)
O3	0.80545 (19)	−0.23713 (10)	0.52116 (7)	0.0179 (3)
N1	0.9833 (2)	−0.28189 (12)	0.22686 (9)	0.0161 (3)
C1	1.0348 (3)	−0.30052 (16)	0.14228 (11)	0.0190 (3)
H1A	1.0992	−0.3781	0.1266	0.023*
C2	0.9938 (3)	−0.20721 (16)	0.07975 (11)	0.0206 (4)
H2A	1.0305	−0.2204	0.0220	0.025*
C3	0.8952 (3)	−0.09151 (16)	0.10463 (11)	0.0204 (4)
H3A	0.8652	−0.0269	0.0632	0.024*
C4	0.8425 (3)	−0.07334 (15)	0.19030 (11)	0.0180 (3)
H4A	0.7758	0.0035	0.2063	0.022*
C5	0.8881 (2)	−0.16930 (15)	0.25392 (11)	0.0162 (3)
C6	0.8438 (3)	−0.15693 (15)	0.34518 (11)	0.0170 (3)
H6A	0.8501	−0.2293	0.3822	0.020*
C7	0.7939 (2)	−0.04592 (15)	0.37962 (10)	0.0156 (3)
H7A	0.7785	0.0241	0.3408	0.019*
C8	0.7615 (2)	−0.02274 (14)	0.46947 (10)	0.0146 (3)
C9	0.7239 (2)	0.10386 (14)	0.48848 (10)	0.0151 (3)
H9A	0.7169	0.1661	0.4435	0.018*
C10	0.6973 (2)	0.13751 (14)	0.57154 (10)	0.0145 (3)
C11	0.7094 (2)	0.04381 (14)	0.63954 (10)	0.0146 (3)
C12	0.7439 (2)	−0.08119 (14)	0.62344 (10)	0.0157 (3)
H12A	0.7494	−0.1428	0.6688	0.019*
C13	0.7702 (2)	−0.11436 (14)	0.53926 (11)	0.0147 (3)
C14	1.0358 (3)	−0.38729 (15)	0.29003 (11)	0.0205 (4)
H14A	1.1044	−0.4574	0.2604	0.031*
H14B	0.9164	−0.4098	0.3242	0.031*
H14C	1.1208	−0.3631	0.3266	0.031*
C15	0.6289 (3)	0.35323 (15)	0.52829 (11)	0.0229 (4)
H15A	0.5949	0.4327	0.5519	0.034*
H15B	0.5219	0.3379	0.4997	0.034*
H15C	0.7485	0.3535	0.4879	0.034*
C16	0.7042 (3)	−0.00944 (15)	0.79006 (10)	0.0182 (3)
H16A	0.6872	0.0300	0.8427	0.027*
H16B	0.8338	−0.0583	0.7821	0.027*
H16C	0.6036	−0.0627	0.7925	0.027*
C17	0.8118 (3)	−0.33027 (15)	0.59227 (11)	0.0205 (4)
H17A	0.8410	−0.4116	0.5713	0.031*
H17B	0.6849	−0.3229	0.6280	0.031*
H17C	0.9137	−0.3187	0.6251	0.031*
S1	0.74248 (6)	0.29952 (4)	0.22553 (3)	0.01886 (12)
O4	0.7780 (2)	0.31567 (12)	0.31164 (9)	0.0316 (3)
O5	0.9172 (2)	0.24169 (11)	0.17148 (9)	0.0286 (3)
O6	0.5690 (2)	0.23666 (11)	0.22522 (9)	0.0247 (3)
O7	0.49664 (19)	0.80352 (10)	0.06333 (8)	0.0205 (3)
C18	0.6572 (3)	0.59021 (15)	0.04644 (11)	0.0181 (3)
H18A	0.6807	0.6042	−0.0130	0.022*
C19	0.7175 (3)	0.47361 (15)	0.08730 (11)	0.0181 (3)
H19A	0.7829	0.4095	0.0546	0.022*
C20	0.6816 (2)	0.45156 (14)	0.17576 (11)	0.0161 (3)
C21	0.5851 (3)	0.54790 (15)	0.22507 (11)	0.0178 (3)
H21A	0.5607	0.5335	0.2845	0.021*
C22	0.5252 (3)	0.66499 (15)	0.18597 (11)	0.0179 (3)
H22A	0.4620	0.7293	0.2189	0.021*
C23	0.5608 (3)	0.68533 (14)	0.09672 (11)	0.0160 (3)
C24	0.5288 (3)	0.82721 (16)	−0.02806 (11)	0.0248 (4)
H24A	0.4792	0.9127	−0.0437	0.037*
H24B	0.4596	0.7735	−0.0536	0.037*
H24C	0.6690	0.8113	−0.0482	0.037*
O1W	0.2248 (2)	0.38849 (12)	0.16774 (9)	0.0228 (3)
H2W1	0.320 (5)	0.349 (3)	0.1858 (17)	0.047 (8)*
H1W1	0.134 (4)	0.342 (3)	0.1731 (16)	0.043 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0289 (7)	0.0070 (5)	0.0203 (6)	0.0022 (5)	−0.0065 (5)	−0.0025 (4)
O2	0.0255 (7)	0.0094 (5)	0.0168 (5)	0.0022 (5)	−0.0041 (5)	−0.0017 (4)
O3	0.0261 (7)	0.0076 (5)	0.0194 (6)	0.0010 (5)	−0.0035 (5)	−0.0027 (4)
N1	0.0164 (7)	0.0121 (6)	0.0201 (7)	0.0002 (5)	−0.0046 (5)	−0.0038 (5)
C1	0.0172 (8)	0.0170 (8)	0.0234 (8)	−0.0001 (6)	−0.0026 (7)	−0.0083 (6)
C2	0.0195 (9)	0.0226 (8)	0.0197 (8)	−0.0011 (7)	−0.0023 (7)	−0.0057 (7)
C3	0.0215 (9)	0.0173 (8)	0.0222 (8)	−0.0011 (7)	−0.0049 (7)	−0.0005 (6)
C4	0.0179 (8)	0.0130 (7)	0.0233 (8)	−0.0002 (6)	−0.0043 (7)	−0.0037 (6)
C5	0.0143 (8)	0.0131 (7)	0.0223 (8)	−0.0014 (6)	−0.0039 (6)	−0.0051 (6)
C6	0.0176 (8)	0.0133 (7)	0.0198 (8)	0.0000 (6)	−0.0030 (6)	−0.0019 (6)
C7	0.0143 (8)	0.0132 (7)	0.0189 (7)	0.0003 (6)	−0.0029 (6)	−0.0023 (6)
C8	0.0127 (8)	0.0122 (7)	0.0191 (8)	0.0004 (6)	−0.0031 (6)	−0.0034 (6)
C9	0.0151 (8)	0.0102 (7)	0.0191 (7)	0.0001 (6)	−0.0027 (6)	0.0000 (6)
C10	0.0139 (8)	0.0082 (7)	0.0212 (8)	0.0018 (6)	−0.0037 (6)	−0.0034 (6)
C11	0.0140 (8)	0.0114 (7)	0.0179 (7)	0.0020 (6)	−0.0023 (6)	−0.0037 (6)
C12	0.0177 (8)	0.0099 (7)	0.0187 (8)	0.0003 (6)	−0.0032 (6)	−0.0003 (6)
C13	0.0130 (8)	0.0076 (7)	0.0234 (8)	0.0008 (6)	−0.0026 (6)	−0.0037 (6)
C14	0.0265 (10)	0.0130 (7)	0.0211 (8)	0.0038 (7)	−0.0058 (7)	−0.0028 (6)
C15	0.0365 (11)	0.0087 (7)	0.0243 (8)	−0.0006 (7)	−0.0105 (8)	−0.0002 (6)
C16	0.0240 (9)	0.0128 (7)	0.0171 (7)	0.0008 (6)	−0.0046 (7)	−0.0007 (6)
C17	0.0281 (10)	0.0094 (7)	0.0237 (8)	0.0011 (6)	−0.0068 (7)	−0.0005 (6)
S1	0.0190 (2)	0.01144 (19)	0.0263 (2)	−0.00110 (15)	−0.00810 (17)	0.00317 (15)
O4	0.0422 (9)	0.0235 (7)	0.0317 (7)	−0.0056 (6)	−0.0193 (6)	0.0066 (5)
O5	0.0217 (7)	0.0145 (6)	0.0458 (8)	0.0037 (5)	−0.0020 (6)	0.0016 (5)
O6	0.0238 (7)	0.0155 (6)	0.0354 (7)	−0.0045 (5)	−0.0081 (6)	0.0038 (5)
O7	0.0276 (7)	0.0102 (5)	0.0219 (6)	0.0033 (5)	−0.0037 (5)	−0.0008 (4)
C18	0.0233 (9)	0.0126 (7)	0.0182 (7)	−0.0006 (6)	−0.0029 (7)	−0.0027 (6)
C19	0.0211 (9)	0.0113 (7)	0.0221 (8)	0.0002 (6)	−0.0034 (7)	−0.0052 (6)
C20	0.0149 (8)	0.0111 (7)	0.0230 (8)	−0.0015 (6)	−0.0057 (6)	−0.0009 (6)
C21	0.0186 (9)	0.0164 (8)	0.0185 (8)	−0.0024 (6)	−0.0024 (6)	−0.0018 (6)
C22	0.0187 (8)	0.0132 (7)	0.0214 (8)	0.0009 (6)	−0.0023 (7)	−0.0052 (6)
C23	0.0167 (8)	0.0089 (7)	0.0223 (8)	0.0000 (6)	−0.0053 (6)	−0.0001 (6)
C24	0.0334 (11)	0.0155 (8)	0.0234 (9)	0.0041 (7)	−0.0067 (8)	0.0016 (7)
O1W	0.0200 (7)	0.0185 (6)	0.0297 (7)	0.0000 (6)	−0.0035 (6)	−0.0046 (5)

O1—C10	1.3789 (18)	C14—H14C	0.9600
O1—C15	1.4194 (19)	C15—H15A	0.9600
O2—C11	1.3620 (19)	C15—H15B	0.9600
O2—C16	1.4366 (19)	C15—H15C	0.9600
O3—C13	1.3736 (18)	C16—H16A	0.9600
O3—C17	1.4335 (19)	C16—H16B	0.9600
N1—C1	1.359 (2)	C16—H16C	0.9600
N1—C5	1.375 (2)	C17—H17A	0.9600
N1—C14	1.477 (2)	C17—H17B	0.9600
C1—C2	1.368 (2)	C17—H17C	0.9600
C1—H1A	0.9300	S1—O4	1.4518 (14)
C2—C3	1.400 (2)	S1—O6	1.4602 (13)
C2—H2A	0.9300	S1—O5	1.4603 (14)
C3—C4	1.376 (2)	S1—C20	1.7730 (16)
C3—H3A	0.9300	O7—C23	1.3710 (18)
C4—C5	1.405 (2)	O7—C24	1.431 (2)
C4—H4A	0.9300	C18—C23	1.395 (2)
C5—C6	1.446 (2)	C18—C19	1.395 (2)
C6—C7	1.352 (2)	C18—H18A	0.9300
C6—H6A	0.9300	C19—C20	1.385 (2)
C7—C8	1.448 (2)	C19—H19A	0.9300
C7—H7A	0.9300	C20—C21	1.396 (2)
C8—C13	1.409 (2)	C21—C22	1.387 (2)
C8—C9	1.418 (2)	C21—H21A	0.9300
C9—C10	1.379 (2)	C22—C23	1.396 (2)
C9—H9A	0.9300	C22—H22A	0.9300
C10—C11	1.405 (2)	C24—H24A	0.9600
C11—C12	1.389 (2)	C24—H24B	0.9600
C12—C13	1.394 (2)	C24—H24C	0.9600
C12—H12A	0.9300	O1W—H2W1	0.80 (3)
C14—H14A	0.9600	O1W—H1W1	0.84 (3)
C14—H14B	0.9600
C10—O1—C15	115.80 (12)	O1—C15—H15A	109.5
C11—O2—C16	116.97 (12)	O1—C15—H15B	109.5
C13—O3—C17	117.46 (12)	H15A—C15—H15B	109.5
C1—N1—C5	122.06 (14)	O1—C15—H15C	109.5
C1—N1—C14	117.55 (13)	H15A—C15—H15C	109.5
C5—N1—C14	120.39 (13)	H15B—C15—H15C	109.5
N1—C1—C2	121.19 (15)	O2—C16—H16A	109.5
N1—C1—H1A	119.4	O2—C16—H16B	109.5
C2—C1—H1A	119.4	H16A—C16—H16B	109.5
C1—C2—C3	118.52 (15)	O2—C16—H16C	109.5
C1—C2—H2A	120.7	H16A—C16—H16C	109.5
C3—C2—H2A	120.7	H16B—C16—H16C	109.5
C4—C3—C2	120.05 (16)	O3—C17—H17A	109.5
C4—C3—H3A	120.0	O3—C17—H17B	109.5
C2—C3—H3A	120.0	H17A—C17—H17B	109.5
C3—C4—C5	120.90 (15)	O3—C17—H17C	109.5
C3—C4—H4A	119.5	H17A—C17—H17C	109.5
C5—C4—H4A	119.5	H17B—C17—H17C	109.5
N1—C5—C4	117.27 (14)	O4—S1—O6	112.62 (8)
N1—C5—C6	118.25 (14)	O4—S1—O5	114.15 (9)
C4—C5—C6	124.48 (14)	O6—S1—O5	111.56 (8)
C7—C6—C5	123.58 (15)	O4—S1—C20	106.30 (8)
C7—C6—H6A	118.2	O6—S1—C20	105.60 (7)
C5—C6—H6A	118.2	O5—S1—C20	105.85 (8)
C6—C7—C8	127.96 (15)	C23—O7—C24	117.05 (13)
C6—C7—H7A	116.0	C23—C18—C19	118.51 (15)
C8—C7—H7A	116.0	C23—C18—H18A	120.7
C13—C8—C9	117.33 (14)	C19—C18—H18A	120.7
C13—C8—C7	125.88 (14)	C20—C19—C18	121.16 (15)
C9—C8—C7	116.76 (14)	C20—C19—H19A	119.4
C10—C9—C8	122.01 (14)	C18—C19—H19A	119.4
C10—C9—H9A	119.0	C19—C20—C21	119.53 (15)
C8—C9—H9A	119.0	C19—C20—S1	120.26 (12)
O1—C10—C9	125.62 (14)	C21—C20—S1	120.06 (13)
O1—C10—C11	115.21 (13)	C22—C21—C20	120.38 (15)
C9—C10—C11	119.17 (14)	C22—C21—H21A	119.8
O2—C11—C12	123.81 (14)	C20—C21—H21A	119.8
O2—C11—C10	115.77 (13)	C21—C22—C23	119.36 (15)
C12—C11—C10	120.41 (14)	C21—C22—H22A	120.3
C11—C12—C13	120.01 (14)	C23—C22—H22A	120.3
C11—C12—H12A	120.0	O7—C23—C18	123.36 (15)
C13—C12—H12A	120.0	O7—C23—C22	115.59 (14)
O3—C13—C12	121.44 (14)	C18—C23—C22	121.05 (15)
O3—C13—C8	117.52 (14)	O7—C24—H24A	109.5
C12—C13—C8	121.04 (14)	O7—C24—H24B	109.5
N1—C14—H14A	109.5	H24A—C24—H24B	109.5
N1—C14—H14B	109.5	O7—C24—H24C	109.5
H14A—C14—H14B	109.5	H24A—C24—H24C	109.5
N1—C14—H14C	109.5	H24B—C24—H24C	109.5
H14A—C14—H14C	109.5	H2W1—O1W—H1W1	109 (3)
H14B—C14—H14C	109.5
C5—N1—C1—C2	0.0 (3)	O2—C11—C12—C13	−178.62 (15)
C14—N1—C1—C2	−179.20 (16)	C10—C11—C12—C13	1.1 (3)
N1—C1—C2—C3	−0.6 (3)	C17—O3—C13—C12	0.7 (2)
C1—C2—C3—C4	0.3 (3)	C17—O3—C13—C8	−179.24 (14)
C2—C3—C4—C5	0.7 (3)	C11—C12—C13—O3	179.71 (15)
C1—N1—C5—C4	0.9 (2)	C11—C12—C13—C8	−0.3 (3)
C14—N1—C5—C4	−179.92 (15)	C9—C8—C13—O3	179.62 (14)
C1—N1—C5—C6	−178.33 (15)	C7—C8—C13—O3	−2.5 (2)
C14—N1—C5—C6	0.8 (2)	C9—C8—C13—C12	−0.4 (2)
C3—C4—C5—N1	−1.2 (2)	C7—C8—C13—C12	177.53 (16)
C3—C4—C5—C6	177.98 (16)	C23—C18—C19—C20	0.5 (3)
N1—C5—C6—C7	164.26 (17)	C18—C19—C20—C21	−0.6 (3)
C4—C5—C6—C7	−14.9 (3)	C18—C19—C20—S1	175.15 (13)
C5—C6—C7—C8	−174.98 (16)	O4—S1—C20—C19	153.77 (14)
C6—C7—C8—C13	−2.2 (3)	O6—S1—C20—C19	−86.39 (15)
C6—C7—C8—C9	175.70 (17)	O5—S1—C20—C19	32.02 (16)
C13—C8—C9—C10	0.2 (2)	O4—S1—C20—C21	−30.55 (17)
C7—C8—C9—C10	−177.85 (15)	O6—S1—C20—C21	89.30 (15)
C15—O1—C10—C9	6.4 (2)	O5—S1—C20—C21	−152.29 (14)
C15—O1—C10—C11	−174.21 (15)	C19—C20—C21—C22	0.0 (3)
C8—C9—C10—O1	179.91 (15)	S1—C20—C21—C22	−175.73 (13)
C8—C9—C10—C11	0.6 (3)	C20—C21—C22—C23	0.6 (3)
C16—O2—C11—C12	1.7 (2)	C24—O7—C23—C18	1.2 (2)
C16—O2—C11—C10	−178.06 (14)	C24—O7—C23—C22	−179.31 (15)
O1—C10—C11—O2	−0.9 (2)	C19—C18—C23—O7	179.53 (15)
C9—C10—C11—O2	178.52 (15)	C19—C18—C23—C22	0.1 (3)
O1—C10—C11—C12	179.34 (15)	C21—C22—C23—O7	179.87 (15)
C9—C10—C11—C12	−1.2 (2)	C21—C22—C23—C18	−0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O6	0.80 (3)	2.08 (3)	2.8703 (19)	175 (3)
O1W—H1W1···O5i	0.85 (3)	1.98 (3)	2.8233 (19)	173 (2)
C9—H9A···O4	0.93	2.53	3.445 (2)	167
C14—H14A···O1Wii	0.96	2.32	3.262 (2)	168
C14—H14C···O1iii	0.96	2.54	3.487 (2)	168
C16—H16A···O7iv	0.96	2.53	3.388 (2)	149
C16—H16B···O5iii	0.96	2.54	3.408 (2)	150
C16—H16C···O6v	0.96	2.44	3.371 (2)	163
C17—H17C···O4iii	0.96	2.47	3.419 (2)	168
C18—H18A···O1Wvi	0.93	2.43	3.354 (2)	171
C22—H22A···O2iv	0.93	2.36	3.281 (2)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O6	0.80 (3)	2.08 (3)	2.8703 (19)	175 (3)
O1W—H1W1⋯O5i	0.85 (3)	1.98 (3)	2.8233 (19)	173 (2)
C9—H9A⋯O4	0.93	2.53	3.445 (2)	167
C14—H14A⋯O1Wii	0.96	2.32	3.262 (2)	168
C14—H14C⋯O1iii	0.96	2.54	3.487 (2)	168
C16—H16A⋯O7iv	0.96	2.53	3.388 (2)	149
C16—H16B⋯O5iii	0.96	2.54	3.408 (2)	150
C16—H16C⋯O6v	0.96	2.44	3.371 (2)	163
C17—H17C⋯O4iii	0.96	2.47	3.419 (2)	168
C18—H18A⋯O1Wvi	0.93	2.43	3.354 (2)	171
C22—H22A⋯O2iv	0.93	2.36	3.281 (2)	170

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