(E)-2-[4-(Dimethyl-amino)styr-yl]-1-methyl-quinolinium 4-methoxy-benzene-sulfonate monohydrate.

In the title compound, C(20)H(21)N(2) (+)·C(7)H(7)O(4)S(-)·H(2)O, the cation is nearly planar and exists in the E configuration. The cations and anions form individual chains along the b axis and are inter-connected by weak C-H⋯O inter-actions. The 4-methoxy-benzensulfonate anions are linked to water mol-ecules through O-H⋯O hydrogen bonds, forming a three-dimensional network. The crystal structure is further stabilized by a C-H⋯π inter-action involving the methoxy-phenyl ring. The sulfonate anion is also involved in a weak intra-molecular C-H⋯O inter-action which generates an S(5) ring motif.

Related literature

For bond lengths and angles, see: Allen (2002 ▶); Allen et al. (1987 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to NLO materials research, see: Chia et al., (1995 ▶); Otero et al., (2002 ▶). For related structures, see for example: Chantrapromma et al. (2006 ▶, 2007 ▶, 2007a ▶,b ▶); Jindawong et al. (2005 ▶); Dittrich et al. (2003 ▶); Nogi et al. (2000 ▶); Sato et al. (1999 ▶).

Experimental

Crystal data

C20H21N2 +·C7H7O4S−·H2O

M = 494.60

Monoclinic,

a = 14.6064 (5) Å

b = 10.4253 (4) Å

c = 19.5025 (6) Å

β = 126.737 (2)°

V = 2379.94 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 100.0 (1) K

0.58 × 0.27 × 0.19 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.904, T max = 0.967

33983 measured reflections

6953 independent reflections

5445 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.139

S = 1.06

6953 reflections

350 parameters

H-atom parameters constrained

Δρmax = 0.74 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005205/sj2466sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005205/sj2466Isup2.hkl

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

C20H21N2+·C7H7O4S–·H2O	F000 = 1048
Mr = 494.60	Dx = 1.380 Mg m−3
Monoclinic, P21/c	Melting point = 545–547 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 14.6064 (5) Å	Cell parameters from 6593 reflections
b = 10.4253 (4) Å	θ = 2.1–30.0º
c = 19.5025 (6) Å	µ = 0.18 mm−1
β = 126.737 (2)º	T = 100.0 (1) K
V = 2379.94 (16) Å3	Block, brown
Z = 4	0.58 × 0.27 × 0.19 mm

Bruker SMART APEX2 CCD area-detector diffractometer	6953 independent reflections
Radiation source: fine-focus sealed tube	5445 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 2.1º
ω scans	h = −20→19
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.904, Tmax = 0.967	l = −24→27
33983 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0641P)2 + 1.1852P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
6953 reflections	Δρmax = 0.75 e Å−3
350 parameters	Δρmin = −0.42 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cryosystem Cobra low-temperature attachment.

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
S1	0.61826 (3)	0.05907 (4)	0.76956 (2)	0.02112 (11)
O1	0.95438 (10)	−0.35916 (12)	0.95862 (7)	0.0250 (3)
O2	0.53003 (10)	0.00579 (13)	0.68519 (7)	0.0275 (3)
O3	0.57692 (12)	0.08820 (15)	0.81913 (8)	0.0360 (3)
O4	0.67900 (11)	0.16597 (13)	0.76497 (8)	0.0301 (3)
O1W	0.66931 (11)	0.09083 (15)	0.33524 (10)	0.0429 (4)
H1W	0.6058	0.0660	0.3224	0.058 (8)*
H2W	0.6633	0.1682	0.3187	0.050 (7)*
N1	0.56771 (11)	0.67419 (14)	0.49475 (8)	0.0215 (3)
N2	0.05342 (12)	1.30700 (15)	0.29537 (8)	0.0235 (3)
C1	0.64527 (13)	0.57400 (17)	0.54367 (9)	0.0217 (3)
C2	0.70847 (15)	0.51470 (19)	0.52077 (11)	0.0277 (4)
H2A	0.7021	0.5417	0.4726	0.038 (6)*
C3	0.77995 (16)	0.4162 (2)	0.56969 (11)	0.0322 (4)
H3A	0.8227	0.3772	0.5545	0.055 (7)*
C4	0.79097 (16)	0.37240 (19)	0.64227 (11)	0.0304 (4)
H4A	0.8393	0.3040	0.6737	0.043 (6)*
C5	0.73095 (14)	0.42956 (18)	0.66701 (10)	0.0268 (4)
H5A	0.7384	0.4009	0.7153	0.024 (5)*
C6	0.65650 (13)	0.53407 (17)	0.61789 (10)	0.0229 (3)
C7	0.59337 (14)	0.59648 (18)	0.64128 (10)	0.0237 (3)
H7A	0.5989	0.5687	0.6889	0.026 (5)*
C8	0.52447 (14)	0.69699 (18)	0.59453 (10)	0.0241 (3)
H8A	0.4857	0.7396	0.6120	0.024 (5)*
C9	0.51057 (13)	0.73831 (17)	0.51874 (9)	0.0216 (3)
C10	0.43701 (13)	0.84531 (17)	0.46835 (10)	0.0220 (3)
H10A	0.4384	0.8763	0.4243	0.032 (6)*
C11	0.36646 (13)	0.90197 (17)	0.48240 (9)	0.0211 (3)
H11A	0.3685	0.8710	0.5280	0.033 (6)*
C12	0.28800 (13)	1.00599 (16)	0.43337 (9)	0.0197 (3)
C13	0.22320 (13)	1.05721 (17)	0.45820 (9)	0.0218 (3)
H13A	0.2324	1.0239	0.5062	0.039 (6)*
C14	0.14611 (13)	1.15578 (17)	0.41354 (9)	0.0215 (3)
H14A	0.1048	1.1876	0.4321	0.029 (5)*
C15	0.12911 (12)	1.20908 (16)	0.33990 (9)	0.0188 (3)
C16	0.19398 (13)	1.15699 (17)	0.31446 (9)	0.0202 (3)
H16A	0.1845	1.1893	0.2661	0.025 (5)*
C17	0.27101 (13)	1.05893 (17)	0.36003 (9)	0.0206 (3)
H17A	0.3128	1.0270	0.3419	0.023 (5)*
C18	−0.01161 (15)	1.3601 (2)	0.32301 (11)	0.0292 (4)
H18A	0.0396	1.3844	0.3821	0.029 (5)*
H18B	−0.0642	1.2968	0.3162	0.034 (6)*
H18C	−0.0532	1.4341	0.2890	0.054 (8)*
C19	0.03078 (15)	1.35334 (19)	0.21618 (10)	0.0260 (4)
H19A	0.1000	1.3866	0.2277	0.036 (6)*
H19B	−0.0257	1.4200	0.1926	0.043 (7)*
H19C	0.0031	1.2839	0.1760	0.028 (5)*
C20	0.54745 (16)	0.7057 (2)	0.41323 (11)	0.0288 (4)
H20A	0.4713	0.7384	0.3738	0.051 (7)*
H20B	0.5564	0.6299	0.3898	0.044 (7)*
H20C	0.6014	0.7695	0.4228	0.048 (7)*
C21	0.72090 (13)	−0.06494 (16)	0.82541 (9)	0.0190 (3)
C22	0.68657 (13)	−0.19286 (17)	0.81620 (9)	0.0210 (3)
H22A	0.6094	−0.2136	0.7793	0.024 (5)*
C23	0.76655 (14)	−0.28880 (17)	0.86144 (9)	0.0218 (3)
H23A	0.7432	−0.3737	0.8553	0.032 (6)*
C24	0.88269 (13)	−0.25763 (16)	0.91662 (9)	0.0198 (3)
C25	0.91782 (13)	−0.13092 (16)	0.92572 (9)	0.0209 (3)
H25A	0.9950	−0.1102	0.9623	0.030 (5)*
C26	0.83634 (13)	−0.03516 (17)	0.87967 (9)	0.0207 (3)
H26A	0.8596	0.0497	0.8853	0.021 (5)*
C27	1.07377 (14)	−0.33401 (19)	1.02041 (11)	0.0272 (4)
H27A	1.1131	−0.4129	1.0475	0.024 (5)*
H27B	1.0848	−0.2755	1.0628	0.031 (5)*
H27C	1.1035	−0.2968	0.9924	0.038 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.02159 (18)	0.0248 (2)	0.01629 (17)	0.00406 (15)	0.01098 (14)	0.00242 (14)
O1	0.0220 (5)	0.0216 (6)	0.0234 (5)	0.0026 (5)	0.0093 (4)	0.0033 (5)
O2	0.0230 (6)	0.0336 (7)	0.0176 (5)	0.0029 (5)	0.0077 (5)	0.0016 (5)
O3	0.0390 (7)	0.0486 (9)	0.0284 (6)	0.0158 (7)	0.0244 (6)	0.0072 (6)
O4	0.0289 (6)	0.0248 (7)	0.0309 (6)	0.0018 (5)	0.0148 (5)	0.0054 (5)
O1W	0.0259 (7)	0.0310 (8)	0.0591 (9)	0.0033 (6)	0.0186 (7)	0.0143 (7)
N1	0.0211 (6)	0.0261 (8)	0.0164 (6)	0.0002 (5)	0.0107 (5)	0.0007 (5)
N2	0.0241 (6)	0.0285 (8)	0.0181 (6)	0.0070 (6)	0.0128 (5)	0.0032 (5)
C1	0.0180 (7)	0.0230 (8)	0.0167 (6)	−0.0035 (6)	0.0065 (5)	−0.0007 (6)
C2	0.0264 (8)	0.0331 (10)	0.0228 (7)	0.0006 (7)	0.0143 (7)	−0.0013 (7)
C3	0.0326 (9)	0.0343 (11)	0.0284 (8)	0.0044 (8)	0.0175 (7)	−0.0010 (7)
C4	0.0309 (9)	0.0274 (10)	0.0274 (8)	0.0069 (7)	0.0145 (7)	0.0042 (7)
C5	0.0231 (7)	0.0299 (10)	0.0210 (7)	0.0015 (7)	0.0097 (6)	0.0015 (7)
C6	0.0194 (7)	0.0258 (9)	0.0205 (7)	−0.0050 (6)	0.0102 (6)	−0.0058 (6)
C7	0.0238 (7)	0.0290 (9)	0.0165 (6)	−0.0025 (7)	0.0109 (6)	−0.0001 (6)
C8	0.0213 (7)	0.0291 (9)	0.0210 (7)	0.0012 (7)	0.0121 (6)	0.0021 (6)
C9	0.0176 (6)	0.0240 (9)	0.0205 (7)	−0.0033 (6)	0.0099 (6)	−0.0048 (6)
C10	0.0205 (7)	0.0253 (9)	0.0177 (6)	0.0007 (6)	0.0101 (6)	−0.0001 (6)
C11	0.0207 (7)	0.0237 (8)	0.0171 (6)	−0.0009 (6)	0.0103 (6)	−0.0007 (6)
C12	0.0179 (6)	0.0217 (8)	0.0173 (6)	−0.0011 (6)	0.0094 (5)	−0.0020 (6)
C13	0.0215 (7)	0.0276 (9)	0.0169 (6)	−0.0001 (6)	0.0117 (6)	0.0012 (6)
C14	0.0211 (7)	0.0278 (9)	0.0174 (6)	0.0014 (6)	0.0126 (6)	−0.0017 (6)
C15	0.0169 (6)	0.0208 (8)	0.0158 (6)	−0.0003 (6)	0.0082 (5)	−0.0020 (5)
C16	0.0202 (7)	0.0256 (8)	0.0160 (6)	−0.0007 (6)	0.0114 (6)	−0.0005 (6)
C17	0.0180 (6)	0.0275 (9)	0.0178 (6)	0.0009 (6)	0.0114 (5)	−0.0027 (6)
C18	0.0274 (8)	0.0354 (10)	0.0247 (8)	0.0099 (8)	0.0156 (7)	0.0014 (7)
C19	0.0251 (8)	0.0296 (9)	0.0191 (7)	0.0019 (7)	0.0110 (6)	0.0039 (6)
C20	0.0325 (9)	0.0341 (10)	0.0243 (8)	0.0077 (8)	0.0195 (7)	0.0077 (7)
C21	0.0202 (7)	0.0234 (8)	0.0139 (6)	0.0012 (6)	0.0105 (5)	0.0017 (6)
C22	0.0188 (7)	0.0259 (9)	0.0162 (6)	−0.0012 (6)	0.0093 (6)	0.0004 (6)
C23	0.0247 (7)	0.0210 (8)	0.0178 (6)	−0.0019 (6)	0.0118 (6)	0.0006 (6)
C24	0.0221 (7)	0.0222 (8)	0.0156 (6)	0.0028 (6)	0.0115 (6)	0.0020 (6)
C25	0.0187 (7)	0.0239 (8)	0.0157 (6)	−0.0011 (6)	0.0080 (6)	0.0000 (6)
C26	0.0221 (7)	0.0210 (8)	0.0175 (6)	−0.0016 (6)	0.0110 (6)	−0.0006 (6)
C27	0.0216 (7)	0.0300 (10)	0.0230 (7)	0.0039 (7)	0.0095 (6)	0.0039 (7)

S1—O3	1.4455 (13)	C11—H11A	0.9299
S1—O4	1.4602 (14)	C12—C13	1.401 (2)
S1—O2	1.4628 (12)	C12—C17	1.410 (2)
S1—C21	1.7754 (16)	C13—C14	1.382 (2)
O1—C24	1.3644 (19)	C13—H13A	0.9301
O1—C27	1.431 (2)	C14—C15	1.417 (2)
O1W—H1W	0.8450	C14—H14A	0.9297
O1W—H2W	0.8529	C15—C16	1.415 (2)
N1—C9	1.353 (2)	C16—C17	1.380 (2)
N1—C1	1.411 (2)	C16—H16A	0.9299
N1—C20	1.470 (2)	C17—H17A	0.9299
N2—C15	1.368 (2)	C18—H18A	0.9600
N2—C18	1.453 (2)	C18—H18B	0.9600
N2—C19	1.455 (2)	C18—H18C	0.9600
C1—C2	1.388 (2)	C19—H19A	0.9600
C1—C6	1.418 (2)	C19—H19B	0.9600
C2—C3	1.365 (3)	C19—H19C	0.9600
C2—H2A	0.9299	C20—H20A	0.9600
C3—C4	1.402 (3)	C20—H20B	0.9600
C3—H3A	0.9301	C20—H20C	0.9600
C4—C5	1.365 (3)	C21—C26	1.387 (2)
C4—H4A	0.9300	C21—C22	1.398 (2)
C5—C6	1.429 (2)	C22—C23	1.382 (2)
C5—H5A	0.9301	C22—H22A	0.9300
C6—C7	1.409 (2)	C23—C24	1.399 (2)
C7—C8	1.358 (2)	C23—H23A	0.9301
C7—H7A	0.9300	C24—C25	1.390 (2)
C8—C9	1.433 (2)	C25—C26	1.393 (2)
C8—H8A	0.9301	C25—H25A	0.9300
C9—C10	1.450 (2)	C26—H26A	0.9301
C10—C11	1.350 (2)	C27—H27A	0.9600
C10—H10A	0.9299	C27—H27B	0.9600
C11—C12	1.447 (2)	C27—H27C	0.9600
O3—S1—O4	113.13 (9)	C13—C14—H14A	119.6
O3—S1—O2	113.11 (8)	C15—C14—H14A	119.6
O4—S1—O2	112.31 (8)	N2—C15—C16	121.37 (14)
O3—S1—C21	106.25 (7)	N2—C15—C14	121.43 (14)
O4—S1—C21	105.80 (7)	C16—C15—C14	117.20 (14)
O2—S1—C21	105.44 (8)	C17—C16—C15	121.17 (14)
C24—O1—C27	118.33 (14)	C17—C16—H16A	119.4
H1W—O1W—H2W	109.3	C15—C16—H16A	119.4
C9—N1—C1	122.94 (14)	C16—C17—C12	121.62 (15)
C9—N1—C20	119.79 (14)	C16—C17—H17A	119.2
C1—N1—C20	117.24 (14)	C12—C17—H17A	119.2
C15—N2—C18	120.55 (14)	N2—C18—H18A	109.5
C15—N2—C19	120.40 (14)	N2—C18—H18B	109.5
C18—N2—C19	118.91 (14)	H18A—C18—H18B	109.5
C2—C1—N1	122.11 (15)	N2—C18—H18C	109.5
C2—C1—C6	120.29 (16)	H18A—C18—H18C	109.5
N1—C1—C6	117.60 (15)	H18B—C18—H18C	109.5
C3—C2—C1	119.21 (17)	N2—C19—H19A	109.5
C3—C2—H2A	120.4	N2—C19—H19B	109.5
C1—C2—H2A	120.4	H19A—C19—H19B	109.5
C2—C3—C4	121.91 (18)	N2—C19—H19C	109.5
C2—C3—H3A	119.0	H19A—C19—H19C	109.5
C4—C3—H3A	119.1	H19B—C19—H19C	109.5
C5—C4—C3	120.31 (18)	N1—C20—H20A	109.5
C5—C4—H4A	119.8	N1—C20—H20B	109.5
C3—C4—H4A	119.8	H20A—C20—H20B	109.5
C4—C5—C6	119.22 (16)	N1—C20—H20C	109.5
C4—C5—H5A	120.5	H20A—C20—H20C	109.5
C6—C5—H5A	120.3	H20B—C20—H20C	109.5
C7—C6—C1	119.76 (16)	C26—C21—C22	119.36 (15)
C7—C6—C5	121.21 (16)	C26—C21—S1	120.01 (13)
C1—C6—C5	119.03 (16)	C22—C21—S1	120.63 (11)
C8—C7—C6	120.31 (16)	C23—C22—C21	120.46 (14)
C8—C7—H7A	119.8	C23—C22—H22A	119.7
C6—C7—H7A	119.9	C21—C22—H22A	119.8
C7—C8—C9	121.03 (16)	C22—C23—C24	119.73 (16)
C7—C8—H8A	119.5	C22—C23—H23A	120.1
C9—C8—H8A	119.5	C24—C23—H23A	120.2
N1—C9—C8	118.18 (15)	O1—C24—C25	124.66 (14)
N1—C9—C10	120.42 (14)	O1—C24—C23	115.07 (15)
C8—C9—C10	121.40 (15)	C25—C24—C23	120.28 (15)
C11—C10—C9	123.04 (15)	C24—C25—C26	119.41 (14)
C11—C10—H10A	118.5	C24—C25—H25A	120.3
C9—C10—H10A	118.5	C26—C25—H25A	120.3
C10—C11—C12	126.36 (15)	C21—C26—C25	120.74 (16)
C10—C11—H11A	116.8	C21—C26—H26A	119.6
C12—C11—H11A	116.9	C25—C26—H26A	119.7
C13—C12—C17	117.13 (15)	O1—C27—H27A	109.5
C13—C12—C11	119.28 (14)	O1—C27—H27B	109.5
C17—C12—C11	123.58 (15)	H27A—C27—H27B	109.5
C14—C13—C12	121.99 (15)	O1—C27—H27C	109.5
C14—C13—H13A	119.0	H27A—C27—H27C	109.5
C12—C13—H13A	119.0	H27B—C27—H27C	109.5
C13—C14—C15	120.88 (15)
C9—N1—C1—C2	−175.88 (16)	C12—C13—C14—C15	0.3 (2)
C20—N1—C1—C2	5.9 (2)	C18—N2—C15—C16	−179.39 (16)
C9—N1—C1—C6	4.6 (2)	C19—N2—C15—C16	5.0 (2)
C20—N1—C1—C6	−173.66 (15)	C18—N2—C15—C14	0.4 (2)
N1—C1—C2—C3	−178.39 (16)	C19—N2—C15—C14	−175.14 (15)
C6—C1—C2—C3	1.1 (3)	C13—C14—C15—N2	−179.73 (15)
C1—C2—C3—C4	0.4 (3)	C13—C14—C15—C16	0.1 (2)
C2—C3—C4—C5	−1.1 (3)	N2—C15—C16—C17	179.42 (15)
C3—C4—C5—C6	0.3 (3)	C14—C15—C16—C17	−0.4 (2)
C2—C1—C6—C7	178.90 (16)	C15—C16—C17—C12	0.4 (2)
N1—C1—C6—C7	−1.6 (2)	C13—C12—C17—C16	0.0 (2)
C2—C1—C6—C5	−1.9 (2)	C11—C12—C17—C16	179.05 (15)
N1—C1—C6—C5	177.59 (14)	O3—S1—C21—C26	−97.34 (14)
C4—C5—C6—C7	−179.62 (17)	O4—S1—C21—C26	23.18 (15)
C4—C5—C6—C1	1.2 (2)	O2—S1—C21—C26	142.35 (13)
C1—C6—C7—C8	−1.9 (2)	O3—S1—C21—C22	81.83 (14)
C5—C6—C7—C8	178.93 (16)	O4—S1—C21—C22	−157.66 (13)
C6—C7—C8—C9	2.7 (3)	O2—S1—C21—C22	−38.48 (15)
C1—N1—C9—C8	−3.9 (2)	C26—C21—C22—C23	0.8 (2)
C20—N1—C9—C8	174.28 (15)	S1—C21—C22—C23	−178.35 (12)
C1—N1—C9—C10	176.41 (14)	C21—C22—C23—C24	−0.2 (2)
C20—N1—C9—C10	−5.4 (2)	C27—O1—C24—C25	3.9 (2)
C7—C8—C9—N1	0.2 (2)	C27—O1—C24—C23	−175.95 (14)
C7—C8—C9—C10	179.86 (16)	C22—C23—C24—O1	179.57 (14)
N1—C9—C10—C11	170.96 (15)	C22—C23—C24—C25	−0.3 (2)
C8—C9—C10—C11	−8.7 (2)	O1—C24—C25—C26	−179.62 (14)
C9—C10—C11—C12	−177.83 (15)	C23—C24—C25—C26	0.2 (2)
C10—C11—C12—C13	−177.82 (16)	C22—C21—C26—C25	−0.9 (2)
C10—C11—C12—C17	3.2 (3)	S1—C21—C26—C25	178.29 (12)
C17—C12—C13—C14	−0.3 (2)	C24—C25—C26—C21	0.4 (2)
C11—C12—C13—C14	−179.40 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2i	0.84	2.04	2.875 (3)	169
O1W—H2W···O4ii	0.85	2.10	2.926 (2)	161
C7—H7A···O3iii	0.93	2.49	3.015 (3)	116
C8—H8A···O3iii	0.93	2.57	3.049 (3)	113
C20—H20A···O4iv	0.96	2.46	3.325 (2)	151
C23—H23A···O1Wv	0.93	2.44	3.365 (2)	176
C26—H26A···O4	0.93	2.56	2.921 (2)	104
C27—H27A···O1Wvi	0.96	2.58	3.160 (3)	119
C27—H27A···O1vii	0.96	2.55	3.282 (2)	133
C16—H16A···Cg1iv	0.93	2.81	3.6513 (19)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2i	0.84	2.04	2.875 (3)	169
O1W—H2W⋯O4ii	0.85	2.10	2.926 (2)	161
C7—H7A⋯O3iii	0.93	2.49	3.015 (3)	116
C8—H8A⋯O3iii	0.93	2.57	3.049 (3)	113
C20—H20A⋯O4iv	0.96	2.46	3.325 (2)	151
C23—H23A⋯O1Wv	0.93	2.44	3.365 (2)	176
C26—H26A⋯O4	0.93	2.56	2.921 (2)	104
C27—H27A⋯O1Wvi	0.96	2.58	3.160 (3)	119
C27—H27A⋯O1vii	0.96	2.55	3.282 (2)	133
C16—H16A⋯Cg1iv	0.93	2.81	3.6513 (19)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) . Cg1 is the centroid of the C21–C26 methoxy­phenyl ring.