(E)-2-[4-(Diethyl-amino)-styr-yl]-1-methyl-pyridinium benzene-sulfonate mono-hydrate.

The asymmetric unit of the title compound, C(18)H(23)N(2) (+)·C(6)H(5)O(3)S(-)·H(2)O, comprises a 2-[4-(diethyl-amino)-styr-yl]-1-methyl-pyridinium cation, a benzene-sulfonate anion and a solvent water mol-ecule. One ethyl substituent of the diethyl-amino group of the cation is disordered over two positions in a 0.73789 (9):0.26211 (9) ratio. The cation exists in the E configuration with respect to the C=C bond and the π-conjugated system is essentially planar with a dihedral angle of 0.82 (10)° between the pyridinium and benzene rings. The cation and anion are almost orthogonal with a dihedral angle of 86.71 (10)° between the π-conjugated system of the cation and benzene ring of the anion. In the crystal, mol-ecules are arranged into chains along [001] and adjacent chains are linked by weak C-H⋯O inter-actions. The crystal is further stablilized by O-H⋯O hydrogen bonds and weak C-H⋯π inter-actions.

Related literature

For standard bond lengths, see Allen et al. (1987 ▶). For background to and applications of quaternary ammonium compounds, see: Chanawanno et al. (2010 ▶); Fun et al. (2010 ▶); Massi et al. (2003 ▶); Soprey & Maxcy (1968 ▶); Yabuhara et al. (2004 ▶). For related structures, see: Chanawanno et al. (2010 ▶); Kaewmanee et al. (2010 ▶).

Experimental

Crystal data

C18H23N2 +·C6H5O3S−·H2O

M = 442.57

Monoclinic,

a = 9.9393 (5) Å

b = 17.9047 (9) Å

c = 13.2532 (7) Å

β = 100.715 (1)°

V = 2317.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 297 K

0.47 × 0.28 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector. diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.924, T max = 0.955

23078 measured reflections

6105 independent reflections

3770 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.173

S = 1.04

6105 reflections

293 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.34 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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/S1600536811004156/sj5101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811004156/sj5101Isup2.hkl

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

C18H23N2+·C6H5O3S−·H2O	F(000) = 944
Mr = 442.57	Dx = 1.268 Mg m−3
Monoclinic, P21/c	Melting point = 566–468 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.9393 (5) Å	Cell parameters from 6105 reflections
b = 17.9047 (9) Å	θ = 1.9–29.0°
c = 13.2532 (7) Å	µ = 0.17 mm−1
β = 100.715 (1)°	T = 297 K
V = 2317.4 (2) Å3	Block, orange
Z = 4	0.47 × 0.28 × 0.27 mm

Bruker SMART APEXII CCD area-detector. diffractometer	6105 independent reflections
Radiation source: sealed tube	3770 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 29.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.924, Tmax = 0.955	k = −24→24
23078 measured reflections	l = −17→18

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0718P)2 + 0.6034P] where P = (Fo2 + 2Fc2)/3
6105 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.37923 (17)	0.19719 (9)	0.60635 (12)	0.0544 (4)
N2	0.5404 (2)	−0.11253 (14)	0.11672 (19)	0.0943 (7)
C1	0.3917 (3)	0.24752 (13)	0.68435 (19)	0.0749 (7)
H1A	0.3134	0.2636	0.7070	0.090*
C2	0.5133 (3)	0.27431 (15)	0.7291 (2)	0.0861 (8)
H2A	0.5193	0.3085	0.7826	0.103*
C3	0.6310 (3)	0.25112 (14)	0.69564 (19)	0.0779 (7)
H3A	0.7163	0.2697	0.7260	0.093*
C4	0.6188 (2)	0.20033 (12)	0.61701 (16)	0.0601 (5)
H4A	0.6970	0.1843	0.5943	0.072*
C5	0.49121 (19)	0.17222 (10)	0.57031 (14)	0.0466 (4)
C6	0.47237 (18)	0.12106 (10)	0.48520 (14)	0.0478 (4)
H6A	0.3837	0.1055	0.4583	0.057*
C7	0.57404 (18)	0.09435 (10)	0.44222 (14)	0.0470 (4)
H7A	0.6621	0.1100	0.4708	0.056*
C8	0.56174 (17)	0.04385 (9)	0.35634 (14)	0.0447 (4)
C9	0.67804 (19)	0.02127 (12)	0.31950 (16)	0.0602 (5)
H9A	0.7627	0.0407	0.3498	0.072*
C10	0.6720 (2)	−0.02858 (13)	0.24028 (17)	0.0677 (6)
H10A	0.7524	−0.0421	0.2185	0.081*
C11	0.5480 (2)	−0.05947 (12)	0.19157 (16)	0.0602 (5)
C12	0.4306 (2)	−0.03423 (12)	0.22563 (17)	0.0630 (5)
H12A	0.3453	−0.0516	0.1932	0.076*
C13	0.43791 (19)	0.01503 (11)	0.30494 (16)	0.0568 (5)
H13A	0.3574	0.0298	0.3253	0.068*
C14	0.4085 (3)	−0.14535 (16)	0.0674 (2)	0.0988 (10)
H14A	0.4247	−0.1945	0.0412	0.119*
H14B	0.3509	−0.1514	0.1184	0.119*
C15	0.3368 (4)	−0.09968 (19)	−0.0164 (3)	0.1244 (12)
H15A	0.2533	−0.1241	−0.0475	0.187*
H15B	0.3938	−0.0929	−0.0667	0.187*
H15C	0.3159	−0.0519	0.0098	0.187*
C16A	0.6609 (5)	−0.1534 (2)	0.0964 (3)	0.0785 (14)	0.738 (9)
H16A	0.6350	−0.2045	0.0777	0.094*	0.738 (9)
H16B	0.7302	−0.1546	0.1585	0.094*	0.738 (9)
C17A	0.7198 (5)	−0.1177 (2)	0.0113 (4)	0.0975 (17)	0.738 (9)
H17A	0.7939	−0.1477	−0.0033	0.146*	0.738 (9)
H17B	0.7530	−0.0687	0.0321	0.146*	0.738 (9)
H17C	0.6499	−0.1140	−0.0492	0.146*	0.738 (9)
C16B	0.6536 (13)	−0.1042 (7)	0.0426 (10)	0.080 (4)*	0.262 (9)
H16C	0.6142	−0.1116	−0.0293	0.096*	0.262 (9)
H16D	0.7013	−0.0567	0.0518	0.096*	0.262 (9)
C17B	0.7432 (15)	−0.1684 (7)	0.0869 (10)	0.090 (4)*	0.262 (9)
H17D	0.8044	−0.1811	0.0414	0.135*	0.262 (9)
H17E	0.6870	−0.2108	0.0949	0.135*	0.262 (9)
H17F	0.7953	−0.1544	0.1526	0.135*	0.262 (9)
S1	0.04707 (5)	0.15726 (4)	0.24744 (4)	0.0654 (2)
O1	0.0265 (2)	0.18007 (11)	0.14137 (14)	0.0980 (6)
O2	−0.0623 (2)	0.18000 (11)	0.29822 (16)	0.0985 (6)
O3	0.18028 (17)	0.17776 (11)	0.30344 (15)	0.0916 (6)
C19	0.0540 (2)	0.02197 (16)	0.3415 (2)	0.0776 (7)
H19A	0.0560	0.0495	0.4013	0.093*
C20	0.0584 (3)	−0.0546 (2)	0.3458 (3)	0.1078 (11)
H20A	0.0638	−0.0787	0.4085	0.129*
C21	0.0549 (3)	−0.0958 (2)	0.2577 (5)	0.1239 (16)
H21A	0.0578	−0.1477	0.2608	0.149*
C22	0.0472 (3)	−0.0597 (2)	0.1643 (3)	0.1092 (11)
H22A	0.0446	−0.0874	0.1047	0.131*
C23	0.0431 (2)	0.01794 (17)	0.1597 (2)	0.0815 (7)
H23A	0.0381	0.0423	0.0972	0.098*
C24	0.04664 (18)	0.05846 (14)	0.24854 (17)	0.0618 (5)
C18	0.2404 (2)	0.17099 (14)	0.56214 (19)	0.0718 (6)
H18A	0.2365	0.1176	0.5682	0.108*
H18B	0.2185	0.1848	0.4910	0.108*
H18C	0.1757	0.1934	0.5984	0.108*
O1W	0.8847 (2)	0.20924 (15)	0.49628 (17)	0.1225 (8)
H1W1	0.9246	0.2080	0.4349	0.147*
H2W1	0.9407	0.2522	0.5417	0.147*

	U11	U22	U33	U12	U13	U23
N1	0.0629 (10)	0.0548 (9)	0.0489 (9)	0.0076 (7)	0.0193 (8)	0.0020 (7)
N2	0.0730 (13)	0.1111 (17)	0.0977 (17)	0.0068 (12)	0.0129 (12)	−0.0540 (14)
C1	0.1001 (19)	0.0667 (14)	0.0643 (14)	0.0145 (13)	0.0324 (14)	−0.0063 (12)
C2	0.126 (2)	0.0707 (15)	0.0626 (15)	−0.0013 (16)	0.0201 (16)	−0.0207 (13)
C3	0.0946 (18)	0.0713 (15)	0.0622 (14)	−0.0176 (13)	0.0001 (13)	−0.0076 (12)
C4	0.0608 (12)	0.0635 (12)	0.0542 (12)	−0.0035 (9)	0.0060 (9)	−0.0027 (10)
C5	0.0511 (10)	0.0446 (9)	0.0452 (10)	0.0039 (7)	0.0121 (8)	0.0037 (8)
C6	0.0438 (9)	0.0507 (10)	0.0494 (10)	−0.0008 (7)	0.0096 (8)	−0.0008 (8)
C7	0.0417 (9)	0.0503 (10)	0.0479 (10)	0.0036 (7)	0.0053 (7)	0.0022 (8)
C8	0.0415 (9)	0.0446 (9)	0.0478 (10)	0.0047 (7)	0.0082 (7)	0.0028 (8)
C9	0.0391 (9)	0.0771 (13)	0.0641 (13)	0.0035 (9)	0.0083 (9)	−0.0135 (11)
C10	0.0471 (11)	0.0884 (15)	0.0693 (14)	0.0122 (10)	0.0149 (10)	−0.0182 (12)
C11	0.0587 (12)	0.0614 (12)	0.0602 (12)	0.0083 (9)	0.0099 (10)	−0.0118 (10)
C12	0.0474 (11)	0.0695 (13)	0.0704 (14)	−0.0030 (9)	0.0066 (9)	−0.0172 (11)
C13	0.0429 (10)	0.0630 (12)	0.0660 (13)	0.0021 (8)	0.0139 (9)	−0.0100 (10)
C14	0.116 (2)	0.0828 (18)	0.088 (2)	0.0180 (16)	−0.0052 (17)	−0.0326 (16)
C15	0.157 (3)	0.102 (2)	0.104 (3)	0.030 (2)	−0.003 (2)	−0.008 (2)
C16A	0.083 (3)	0.065 (2)	0.091 (3)	0.0100 (17)	0.027 (2)	−0.0236 (19)
C17A	0.106 (3)	0.096 (3)	0.100 (3)	−0.007 (2)	0.042 (3)	−0.022 (2)
S1	0.0521 (3)	0.0842 (4)	0.0600 (4)	−0.0066 (3)	0.0107 (2)	0.0051 (3)
O1	0.1207 (16)	0.1058 (14)	0.0630 (11)	0.0042 (12)	0.0051 (10)	0.0237 (10)
O2	0.0845 (13)	0.1046 (14)	0.1157 (16)	0.0043 (10)	0.0427 (12)	−0.0098 (12)
O3	0.0688 (11)	0.1090 (14)	0.0908 (13)	−0.0309 (10)	−0.0008 (9)	0.0101 (11)
C19	0.0459 (11)	0.1011 (19)	0.0840 (17)	−0.0052 (11)	0.0073 (11)	0.0224 (15)
C20	0.0568 (16)	0.111 (3)	0.151 (3)	−0.0014 (16)	0.0091 (18)	0.052 (2)
C21	0.0538 (16)	0.085 (2)	0.229 (5)	0.0030 (14)	0.016 (2)	0.023 (3)
C22	0.0698 (18)	0.098 (2)	0.161 (3)	0.0011 (16)	0.022 (2)	−0.028 (2)
C23	0.0588 (14)	0.100 (2)	0.0860 (18)	−0.0017 (13)	0.0138 (12)	−0.0064 (15)
C24	0.0338 (9)	0.0847 (15)	0.0659 (13)	−0.0028 (9)	0.0066 (8)	0.0094 (12)
C18	0.0523 (12)	0.0903 (17)	0.0775 (16)	0.0081 (11)	0.0242 (11)	0.0007 (13)
O1W	0.1150 (17)	0.157 (2)	0.1059 (16)	−0.0526 (15)	0.0468 (13)	−0.0250 (15)

N1—C1	1.360 (3)	C15—H15B	0.9600
N1—C5	1.365 (2)	C15—H15C	0.9600
N1—C18	1.472 (3)	C16A—C17A	1.506 (7)
N2—C11	1.365 (3)	C16A—H16A	0.9700
N2—C16A	1.471 (4)	C16A—H16B	0.9700
N2—C14	1.474 (4)	C17A—H17A	0.9600
N2—C16B	1.632 (14)	C17A—H17B	0.9600
C1—C2	1.333 (4)	C17A—H17C	0.9600
C1—H1A	0.9300	C16B—C17B	1.51 (2)
C2—C3	1.389 (4)	C16B—H16C	0.9700
C2—H2A	0.9300	C16B—H16D	0.9700
C3—C4	1.371 (3)	C17B—H17D	0.9600
C3—H3A	0.9300	C17B—H17E	0.9600
C4—C5	1.397 (3)	C17B—H17F	0.9600
C4—H4A	0.9300	S1—O2	1.4395 (18)
C5—C6	1.438 (3)	S1—O3	1.4398 (17)
C6—C7	1.337 (2)	S1—O1	1.4414 (18)
C6—H6A	0.9300	S1—C24	1.769 (2)
C7—C8	1.441 (2)	C19—C20	1.372 (4)
C7—H7A	0.9300	C19—C24	1.384 (3)
C8—C13	1.390 (3)	C19—H19A	0.9300
C8—C9	1.396 (2)	C20—C21	1.376 (5)
C9—C10	1.371 (3)	C20—H20A	0.9300
C9—H9A	0.9300	C21—C22	1.385 (5)
C10—C11	1.396 (3)	C21—H21A	0.9300
C10—H10A	0.9300	C22—C23	1.391 (4)
C11—C12	1.401 (3)	C22—H22A	0.9300
C12—C13	1.364 (3)	C23—C24	1.377 (3)
C12—H12A	0.9300	C23—H23A	0.9300
C13—H13A	0.9300	C18—H18A	0.9600
C14—C15	1.454 (4)	C18—H18B	0.9600
C14—H14A	0.9700	C18—H18C	0.9600
C14—H14B	0.9700	O1W—H1W1	0.9693
C15—H15A	0.9600	O1W—H2W1	1.0669
C1—N1—C5	121.22 (19)	C14—C15—H15B	109.5
C1—N1—C18	117.38 (19)	H15A—C15—H15B	109.5
C5—N1—C18	121.40 (17)	C14—C15—H15C	109.5
C11—N2—C16A	122.8 (2)	H15A—C15—H15C	109.5
C11—N2—C14	121.6 (2)	H15B—C15—H15C	109.5
C16A—N2—C14	114.1 (2)	N2—C16A—C17A	111.7 (4)
C11—N2—C16B	115.0 (5)	N2—C16A—H16A	109.3
C14—N2—C16B	115.2 (5)	C17A—C16A—H16A	109.3
C2—C1—N1	121.5 (2)	N2—C16A—H16B	109.3
C2—C1—H1A	119.2	C17A—C16A—H16B	109.3
N1—C1—H1A	119.2	H16A—C16A—H16B	108.0
C1—C2—C3	119.9 (2)	C17B—C16B—N2	96.9 (10)
C1—C2—H2A	120.0	C17B—C16B—H16C	112.4
C3—C2—H2A	120.0	N2—C16B—H16C	112.4
C4—C3—C2	118.7 (2)	C17B—C16B—H16D	112.4
C4—C3—H3A	120.7	N2—C16B—H16D	112.4
C2—C3—H3A	120.7	H16C—C16B—H16D	109.9
C3—C4—C5	121.3 (2)	C16B—C17B—H17D	109.5
C3—C4—H4A	119.3	C16B—C17B—H17E	109.5
C5—C4—H4A	119.3	H17D—C17B—H17E	109.5
N1—C5—C4	117.31 (17)	C16B—C17B—H17F	109.5
N1—C5—C6	119.16 (17)	H17D—C17B—H17F	109.5
C4—C5—C6	123.50 (17)	H17E—C17B—H17F	109.5
C7—C6—C5	124.29 (17)	O2—S1—O3	112.89 (13)
C7—C6—H6A	117.9	O2—S1—O1	113.17 (13)
C5—C6—H6A	117.9	O3—S1—O1	112.36 (12)
C6—C7—C8	126.94 (17)	O2—S1—C24	106.01 (11)
C6—C7—H7A	116.5	O3—S1—C24	104.71 (11)
C8—C7—H7A	116.5	O1—S1—C24	106.92 (12)
C13—C8—C9	115.87 (17)	C20—C19—C24	120.3 (3)
C13—C8—C7	123.87 (16)	C20—C19—H19A	119.9
C9—C8—C7	120.26 (16)	C24—C19—H19A	119.9
C10—C9—C8	122.39 (18)	C19—C20—C21	120.3 (3)
C10—C9—H9A	118.8	C19—C20—H20A	119.8
C8—C9—H9A	118.8	C21—C20—H20A	119.8
C9—C10—C11	121.40 (18)	C20—C21—C22	119.7 (4)
C9—C10—H10A	119.3	C20—C21—H21A	120.1
C11—C10—H10A	119.3	C22—C21—H21A	120.1
N2—C11—C10	122.44 (19)	C21—C22—C23	120.1 (4)
N2—C11—C12	121.4 (2)	C21—C22—H22A	119.9
C10—C11—C12	116.11 (19)	C23—C22—H22A	119.9
C13—C12—C11	121.91 (19)	C24—C23—C22	119.5 (3)
C13—C12—H12A	119.0	C24—C23—H23A	120.2
C11—C12—H12A	119.0	C22—C23—H23A	120.2
C12—C13—C8	122.21 (17)	C23—C24—C19	120.0 (3)
C12—C13—H13A	118.9	C23—C24—S1	121.29 (19)
C8—C13—H13A	118.9	C19—C24—S1	118.6 (2)
C15—C14—N2	112.6 (3)	N1—C18—H18A	109.5
C15—C14—H14A	109.1	N1—C18—H18B	109.5
N2—C14—H14A	109.1	H18A—C18—H18B	109.5
C15—C14—H14B	109.1	N1—C18—H18C	109.5
N2—C14—H14B	109.1	H18A—C18—H18C	109.5
H14A—C14—H14B	107.8	H18B—C18—H18C	109.5
C14—C15—H15A	109.5	H1W1—O1W—H2W1	103.8
C5—N1—C1—C2	−0.3 (3)	C10—C11—C12—C13	−2.9 (4)
C18—N1—C1—C2	180.0 (2)	C11—C12—C13—C8	0.6 (4)
N1—C1—C2—C3	0.4 (4)	C9—C8—C13—C12	2.1 (3)
C1—C2—C3—C4	−0.4 (4)	C7—C8—C13—C12	−178.2 (2)
C2—C3—C4—C5	0.3 (3)	C11—N2—C14—C15	83.8 (4)
C1—N1—C5—C4	0.2 (3)	C16A—N2—C14—C15	−109.7 (3)
C18—N1—C5—C4	179.92 (18)	C16B—N2—C14—C15	−63.0 (6)
C1—N1—C5—C6	−177.75 (18)	C11—N2—C16A—C17A	−95.3 (4)
C18—N1—C5—C6	2.0 (3)	C14—N2—C16A—C17A	98.4 (4)
C3—C4—C5—N1	−0.2 (3)	C16B—N2—C16A—C17A	−3.2 (7)
C3—C4—C5—C6	177.6 (2)	C11—N2—C16B—C17B	106.1 (7)
N1—C5—C6—C7	178.44 (17)	C16A—N2—C16B—C17B	−6.1 (5)
C4—C5—C6—C7	0.7 (3)	C14—N2—C16B—C17B	−104.8 (7)
C5—C6—C7—C8	−179.19 (17)	C24—C19—C20—C21	−0.3 (4)
C6—C7—C8—C13	−0.1 (3)	C19—C20—C21—C22	0.1 (4)
C6—C7—C8—C9	179.54 (19)	C20—C21—C22—C23	0.1 (4)
C13—C8—C9—C10	−2.6 (3)	C21—C22—C23—C24	−0.1 (4)
C7—C8—C9—C10	177.8 (2)	C22—C23—C24—C19	0.0 (3)
C8—C9—C10—C11	0.2 (4)	C22—C23—C24—S1	178.04 (19)
C16A—N2—C11—C10	13.7 (4)	C20—C19—C24—C23	0.3 (3)
C14—N2—C11—C10	179.0 (3)	C20—C19—C24—S1	−177.88 (18)
C16B—N2—C11—C10	−34.1 (6)	O2—S1—C24—C23	127.83 (19)
C16A—N2—C11—C12	−164.7 (3)	O3—S1—C24—C23	−112.59 (18)
C14—N2—C11—C12	0.6 (4)	O1—S1—C24—C23	6.8 (2)
C16B—N2—C11—C12	147.5 (5)	O2—S1—C24—C19	−54.06 (19)
C9—C10—C11—N2	−176.0 (2)	O3—S1—C24—C19	65.52 (19)
C9—C10—C11—C12	2.5 (4)	O1—S1—C24—C19	−175.08 (17)
N2—C11—C12—C13	175.6 (2)

Cg1 is the centroid of the C19–C24 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2i	0.97	1.91	2.821 (3)	156
O1W—H2W1···O1ii	1.07	1.88	2.933 (3)	170
C1—H1A···O3iii	0.93	2.26	3.151 (3)	160
C3—H3A···O2ii	0.93	2.41	3.335 (4)	178
C4—H4A···O1W	0.93	2.50	3.338 (3)	149
C18—H18B···O3	0.96	2.45	3.371 (3)	162
C10—H10A···Cg1i	0.93	2.95	3.741 (2)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C19–C24 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2i	0.97	1.91	2.821 (3)	156
O1W—H2W1⋯O1ii	1.07	1.88	2.933 (3)	170
C1—H1A⋯O3iii	0.93	2.26	3.151 (3)	160
C3—H3A⋯O2ii	0.93	2.41	3.335 (4)	178
C4—H4A⋯O1W	0.93	2.50	3.338 (3)	149
C18—H18B⋯O3	0.96	2.45	3.371 (3)	162
C10—H10A⋯Cg1i	0.93	2.95	3.741 (2)	144

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