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

In the title hydrated mol-ecular salt, C(18)H(23)N(2) (+)·C(6)H(4)ClO(3)S(-)·H(2)O, which shows moderate biological activity against methicillin-resistant Staphylococcus aureus (MRSA), one ethyl group of the 2-[4-(diethyl-amino)-styr-yl]-1-methyl-pyridinium cation is disordered over two orientations in a 0.604 (13):0.396 (13) ratio. The main part of the cation is nearly planar with a dihedral angle of 4.50 (10)° between the pyridinium and benzene rings. In the crystal, the components are linked by O-H⋯O hydrogen bonds and C-H⋯O weak inter-actions. Aromatic π-π stacking inter-actions with centroid-centroid separations of 3.7363 (12) and 3.7490 (13) Å also occur.

Related literature

For background to and the application of quarternary ammonium compounds as disinfecta­nts, see: Brown & Skurray (2001 ▶); Chanawanno, Chantrapromma, Anantapong, Kanjana-Opas & Fun (2010 ▶); Domagk (1935 ▶); Endo et al. (1987 ▶); Fun et al. (2011 ▶); Wainwright & Kristiansen (2003 ▶). For a related structure, see: Fun et al. (2011 ▶); Kaewmanee et al. (2010 ▶). For the synthesis, see: Chanawanno, Chantrapromma, Anantapong & Kanjana-Opas (2010 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H23N2 +·C6H4ClO3S−·H2O

M = 477.00

Triclinic,

a = 7.2511 (3) Å

b = 10.2272 (4) Å

c = 16.7169 (7) Å

α = 88.441 (3)°

β = 80.057 (2)°

γ = 77.062 (2)°

V = 1190.00 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 100 K

0.53 × 0.25 × 0.04 mm

Data collection

Bruker APEX Duo CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.866, T max = 0.990

15554 measured reflections

4617 independent reflections

3369 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.04

4617 reflections

320 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.32 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 datablock(s) global, I. DOI: 10.1107/S1600536811034258/hb6382sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034258/hb6382Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811034258/hb6382Isup3.cml

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

C18H23N2+·C6H4ClO3S−·H2O	Z = 2
Mr = 477.00	F(000) = 504
Triclinic, P1	Dx = 1.331 Mg m−3
Hall symbol: -P 1	Melting point = 446–448 K
a = 7.2511 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2272 (4) Å	Cell parameters from 4617 reflections
c = 16.7169 (7) Å	θ = 2.0–26.0°
α = 88.441 (3)°	µ = 0.28 mm−1
β = 80.057 (2)°	T = 296 K
γ = 77.062 (2)°	Plate, orange
V = 1190.00 (8) Å3	0.53 × 0.25 × 0.04 mm

Bruker APEX Duo CCD diffractometer	4617 independent reflections
Radiation source: sealed tube	3369 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.866, Tmax = 0.990	k = −12→12
15554 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3949P] where P = (Fo2 + 2Fc2)/3
4617 reflections	(Δ/σ)max = 0.001
320 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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)
Cl1	−0.43901 (10)	1.01358 (9)	0.38727 (5)	0.0885 (3)
S1	0.36666 (7)	0.85852 (5)	0.16430 (4)	0.04745 (17)
O1	0.4113 (2)	0.98202 (16)	0.13126 (11)	0.0731 (5)
O2	0.3361 (2)	0.77323 (18)	0.10248 (11)	0.0719 (5)
O3	0.4986 (2)	0.79002 (17)	0.21510 (11)	0.0669 (5)
N1	1.0111 (2)	0.50652 (16)	0.11414 (10)	0.0417 (4)
N2	−0.1490 (3)	0.4451 (2)	0.37633 (15)	0.0787 (7)
C1	1.1941 (3)	0.4789 (2)	0.07236 (13)	0.0502 (5)
H1A	1.2646	0.5451	0.0676	0.060*
C2	1.2759 (3)	0.3571 (2)	0.03751 (14)	0.0570 (6)
H2A	1.4011	0.3395	0.0091	0.068*
C3	1.1701 (4)	0.2594 (2)	0.04490 (14)	0.0587 (6)
H3A	1.2239	0.1750	0.0215	0.070*
C4	0.9856 (3)	0.2870 (2)	0.08674 (14)	0.0521 (6)
H4A	0.9146	0.2210	0.0908	0.063*
C5	0.9018 (3)	0.4124 (2)	0.12341 (12)	0.0413 (5)
C6	0.7102 (3)	0.4465 (2)	0.17040 (13)	0.0471 (5)
H6A	0.6627	0.5346	0.1889	0.056*
C7	0.5968 (3)	0.3595 (2)	0.18895 (13)	0.0478 (5)
H7A	0.6453	0.2731	0.1678	0.057*
C8	0.4073 (3)	0.3844 (2)	0.23826 (12)	0.0430 (5)
C9	0.3068 (3)	0.2820 (2)	0.25040 (14)	0.0506 (5)
H9A	0.3640	0.1985	0.2263	0.061*
C10	0.1273 (3)	0.2995 (2)	0.29644 (14)	0.0518 (5)
H10A	0.0667	0.2279	0.3035	0.062*
C11	0.0335 (3)	0.4238 (2)	0.33314 (14)	0.0524 (6)
C12	0.1351 (3)	0.5271 (2)	0.32114 (14)	0.0530 (6)
H12A	0.0785	0.6107	0.3451	0.064*
C13	0.3153 (3)	0.5076 (2)	0.27510 (13)	0.0479 (5)
H13A	0.3774	0.5785	0.2684	0.057*
C14	−0.2465 (4)	0.3354 (3)	0.39602 (17)	0.0684 (7)
H14A	−0.2227	0.2776	0.3486	0.082*
H14B	−0.3838	0.3722	0.4087	0.082*
C15	−0.1841 (5)	0.2521 (3)	0.46642 (18)	0.0881 (9)
H15A	−0.2525	0.1814	0.4758	0.132*
H15B	−0.2114	0.3078	0.5142	0.132*
H15C	−0.0487	0.2141	0.4541	0.132*
C18	0.9351 (3)	0.6428 (2)	0.14925 (15)	0.0536 (6)
H18A	1.0313	0.6947	0.1363	0.080*
H18B	0.9016	0.6372	0.2072	0.080*
H18C	0.8231	0.6852	0.1271	0.080*
C19	0.1250 (3)	0.8958 (2)	0.31157 (14)	0.0518 (6)
H19A	0.2346	0.8653	0.3346	0.062*
C20	−0.0530 (4)	0.9297 (3)	0.36085 (14)	0.0598 (6)
H20A	−0.0638	0.9228	0.4170	0.072*
C21	−0.2136 (3)	0.9736 (2)	0.32577 (14)	0.0526 (6)
C22	−0.2011 (3)	0.9859 (2)	0.24371 (14)	0.0505 (5)
H22A	−0.3114	1.0157	0.2210	0.061*
C23	−0.0230 (3)	0.9535 (2)	0.19461 (13)	0.0446 (5)
H23A	−0.0127	0.9629	0.1386	0.053*
C24	0.1407 (3)	0.90710 (19)	0.22881 (12)	0.0400 (5)
O1W	0.7231 (3)	1.0760 (3)	0.04924 (15)	0.0793 (6)
C16A	−0.2701 (8)	0.5883 (8)	0.3938 (4)	0.0633 (19)	0.604 (13)
H16A	−0.2270	0.6490	0.3529	0.076*	0.604 (13)
H16B	−0.4041	0.5906	0.3928	0.076*	0.604 (13)
C17A	−0.2473 (8)	0.6301 (8)	0.4756 (4)	0.084 (2)	0.604 (13)
H17A	−0.3215	0.7197	0.4877	0.125*	0.604 (13)
H17B	−0.1143	0.6275	0.4761	0.125*	0.604 (13)
H17C	−0.2914	0.5700	0.5157	0.125*	0.604 (13)
C16B	−0.2117 (11)	0.5539 (10)	0.4408 (6)	0.054 (3)	0.396 (13)
H16C	−0.1036	0.5870	0.4524	0.065*	0.396 (13)
H16D	−0.2780	0.5229	0.4906	0.065*	0.396 (13)
C17B	−0.3475 (16)	0.6607 (11)	0.3998 (6)	0.084 (3)	0.396 (13)
H17D	−0.4024	0.7355	0.4363	0.126*	0.396 (13)
H17E	−0.4482	0.6232	0.3860	0.126*	0.396 (13)
H17F	−0.2772	0.6904	0.3513	0.126*	0.396 (13)
H2W1	0.630 (4)	1.048 (3)	0.0698 (17)	0.073 (10)*
H1W1	0.697 (5)	1.109 (4)	0.003 (2)	0.111 (14)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0520 (4)	0.1114 (6)	0.0905 (5)	−0.0164 (4)	0.0210 (4)	−0.0234 (4)
S1	0.0366 (3)	0.0405 (3)	0.0620 (4)	−0.0105 (2)	0.0036 (2)	−0.0030 (2)
O1	0.0612 (11)	0.0534 (10)	0.0986 (14)	−0.0201 (8)	0.0104 (10)	0.0177 (9)
O2	0.0571 (10)	0.0803 (12)	0.0747 (11)	−0.0242 (9)	0.0155 (9)	−0.0323 (10)
O3	0.0387 (9)	0.0646 (11)	0.0905 (12)	0.0004 (8)	−0.0082 (8)	0.0063 (9)
N1	0.0351 (9)	0.0417 (9)	0.0464 (9)	−0.0070 (7)	−0.0027 (7)	−0.0046 (8)
N2	0.0593 (13)	0.0663 (14)	0.1036 (18)	−0.0285 (11)	0.0279 (12)	−0.0248 (13)
C1	0.0364 (11)	0.0580 (14)	0.0547 (13)	−0.0115 (10)	−0.0021 (10)	−0.0019 (11)
C2	0.0392 (12)	0.0628 (15)	0.0600 (14)	−0.0004 (11)	0.0026 (10)	−0.0057 (12)
C3	0.0592 (15)	0.0479 (13)	0.0583 (14)	0.0043 (12)	−0.0002 (12)	−0.0084 (11)
C4	0.0539 (14)	0.0397 (12)	0.0587 (13)	−0.0075 (10)	−0.0017 (11)	−0.0023 (10)
C5	0.0395 (11)	0.0400 (11)	0.0436 (11)	−0.0082 (9)	−0.0054 (9)	0.0000 (9)
C6	0.0431 (12)	0.0415 (12)	0.0536 (12)	−0.0091 (10)	0.0005 (10)	−0.0050 (10)
C7	0.0452 (12)	0.0420 (12)	0.0539 (13)	−0.0082 (10)	−0.0037 (10)	−0.0012 (10)
C8	0.0431 (12)	0.0425 (12)	0.0450 (11)	−0.0137 (9)	−0.0063 (9)	0.0016 (9)
C9	0.0491 (13)	0.0403 (12)	0.0606 (14)	−0.0105 (10)	−0.0028 (11)	−0.0044 (10)
C10	0.0504 (13)	0.0477 (13)	0.0600 (14)	−0.0215 (10)	−0.0023 (11)	−0.0025 (11)
C11	0.0462 (13)	0.0554 (14)	0.0549 (13)	−0.0182 (11)	0.0036 (10)	−0.0045 (11)
C12	0.0531 (13)	0.0450 (13)	0.0584 (13)	−0.0135 (11)	0.0026 (11)	−0.0099 (10)
C13	0.0497 (13)	0.0445 (12)	0.0521 (12)	−0.0193 (10)	−0.0041 (10)	−0.0009 (10)
C14	0.0514 (14)	0.0794 (18)	0.0754 (17)	−0.0292 (13)	0.0069 (13)	−0.0073 (14)
C15	0.094 (2)	0.103 (2)	0.0773 (19)	−0.0458 (19)	−0.0084 (17)	−0.0045 (18)
C18	0.0492 (13)	0.0458 (12)	0.0646 (14)	−0.0124 (10)	−0.0019 (11)	−0.0135 (11)
C19	0.0433 (12)	0.0552 (14)	0.0551 (13)	−0.0051 (10)	−0.0108 (10)	0.0004 (11)
C20	0.0592 (15)	0.0694 (16)	0.0466 (13)	−0.0098 (12)	−0.0026 (11)	−0.0033 (11)
C21	0.0419 (12)	0.0516 (13)	0.0603 (14)	−0.0114 (10)	0.0056 (11)	−0.0100 (11)
C22	0.0389 (12)	0.0472 (13)	0.0642 (15)	−0.0049 (10)	−0.0103 (11)	−0.0056 (11)
C23	0.0425 (12)	0.0415 (11)	0.0488 (12)	−0.0068 (9)	−0.0085 (10)	−0.0013 (9)
C24	0.0375 (11)	0.0299 (10)	0.0519 (12)	−0.0098 (8)	−0.0026 (9)	−0.0027 (9)
O1W	0.0702 (14)	0.1094 (18)	0.0700 (14)	−0.0476 (13)	−0.0091 (11)	0.0081 (12)
C16A	0.042 (3)	0.073 (5)	0.070 (4)	−0.010 (3)	0.000 (3)	0.000 (3)
C17A	0.077 (4)	0.090 (5)	0.076 (4)	−0.013 (3)	0.004 (3)	−0.024 (4)
C16B	0.049 (4)	0.064 (6)	0.048 (5)	−0.015 (4)	0.005 (3)	0.000 (4)
C17B	0.072 (6)	0.061 (6)	0.102 (7)	0.012 (5)	0.001 (5)	0.003 (5)

Cl1—C21	1.743 (2)	C13—H13A	0.9300
S1—O3	1.4406 (17)	C14—C15	1.507 (4)
S1—O1	1.4453 (16)	C14—H14A	0.9700
S1—O2	1.4466 (17)	C14—H14B	0.9700
S1—C24	1.775 (2)	C15—H15A	0.9600
N1—C1	1.361 (3)	C15—H15B	0.9600
N1—C5	1.367 (3)	C15—H15C	0.9600
N1—C18	1.477 (3)	C18—H18A	0.9600
N2—C11	1.367 (3)	C18—H18B	0.9600
N2—C14	1.456 (3)	C18—H18C	0.9600
N2—C16B	1.508 (11)	C19—C24	1.372 (3)
N2—C16A	1.537 (8)	C19—C20	1.383 (3)
C1—C2	1.354 (3)	C19—H19A	0.9300
C1—H1A	0.9300	C20—C21	1.375 (3)
C2—C3	1.381 (3)	C20—H20A	0.9300
C2—H2A	0.9300	C21—C22	1.363 (3)
C3—C4	1.370 (3)	C22—C23	1.382 (3)
C3—H3A	0.9300	C22—H22A	0.9300
C4—C5	1.398 (3)	C23—C24	1.389 (3)
C4—H4A	0.9300	C23—H23A	0.9300
C5—C6	1.446 (3)	O1W—H2W1	0.81 (3)
C6—C7	1.337 (3)	O1W—H1W1	0.86 (4)
C6—H6A	0.9300	C16A—C17A	1.490 (11)
C7—C8	1.448 (3)	C16A—H16A	0.9700
C7—H7A	0.9300	C16A—H16B	0.9700
C8—C13	1.391 (3)	C17A—H17A	0.9600
C8—C9	1.397 (3)	C17A—H17B	0.9600
C9—C10	1.370 (3)	C17A—H17C	0.9600
C9—H9A	0.9300	C16B—C17B	1.531 (15)
C10—C11	1.402 (3)	C16B—H16C	0.9700
C10—H10A	0.9300	C16B—H16D	0.9700
C11—C12	1.408 (3)	C17B—H17D	0.9600
C12—C13	1.372 (3)	C17B—H17E	0.9600
C12—H12A	0.9300	C17B—H17F	0.9600
O3—S1—O1	113.45 (11)	N2—C14—H14A	108.8
O3—S1—O2	113.60 (11)	C15—C14—H14A	108.8
O1—S1—O2	112.13 (12)	N2—C14—H14B	108.8
O3—S1—C24	106.07 (10)	C15—C14—H14B	108.8
O1—S1—C24	105.37 (10)	H14A—C14—H14B	107.7
O2—S1—C24	105.31 (9)	C14—C15—H15A	109.5
C1—N1—C5	121.61 (18)	C14—C15—H15B	109.5
C1—N1—C18	117.11 (18)	H15A—C15—H15B	109.5
C5—N1—C18	121.27 (17)	C14—C15—H15C	109.5
C11—N2—C14	121.6 (2)	H15A—C15—H15C	109.5
C11—N2—C16B	118.8 (3)	H15B—C15—H15C	109.5
C14—N2—C16B	111.8 (3)	N1—C18—H18A	109.5
C11—N2—C16A	120.6 (3)	N1—C18—H18B	109.5
C14—N2—C16A	117.1 (3)	H18A—C18—H18B	109.5
C2—C1—N1	121.5 (2)	N1—C18—H18C	109.5
C2—C1—H1A	119.3	H18A—C18—H18C	109.5
N1—C1—H1A	119.3	H18B—C18—H18C	109.5
C1—C2—C3	118.8 (2)	C24—C19—C20	120.3 (2)
C1—C2—H2A	120.6	C24—C19—H19A	119.9
C3—C2—H2A	120.6	C20—C19—H19A	119.9
C4—C3—C2	119.9 (2)	C21—C20—C19	119.1 (2)
C4—C3—H3A	120.1	C21—C20—H20A	120.4
C2—C3—H3A	120.1	C19—C20—H20A	120.4
C3—C4—C5	121.3 (2)	C22—C21—C20	121.5 (2)
C3—C4—H4A	119.3	C22—C21—Cl1	119.02 (18)
C5—C4—H4A	119.3	C20—C21—Cl1	119.46 (19)
N1—C5—C4	116.93 (19)	C21—C22—C23	119.3 (2)
N1—C5—C6	119.05 (18)	C21—C22—H22A	120.4
C4—C5—C6	124.0 (2)	C23—C22—H22A	120.4
C7—C6—C5	124.14 (19)	C22—C23—C24	120.0 (2)
C7—C6—H6A	117.9	C22—C23—H23A	120.0
C5—C6—H6A	117.9	C24—C23—H23A	120.0
C6—C7—C8	127.4 (2)	C19—C24—C23	119.73 (19)
C6—C7—H7A	116.3	C19—C24—S1	120.97 (16)
C8—C7—H7A	116.3	C23—C24—S1	119.28 (16)
C13—C8—C9	116.57 (19)	H2W1—O1W—H1W1	105 (3)
C13—C8—C7	123.52 (19)	C17A—C16A—N2	108.1 (7)
C9—C8—C7	119.92 (19)	C17A—C16A—H16A	110.1
C10—C9—C8	122.6 (2)	N2—C16A—H16A	110.1
C10—C9—H9A	118.7	C17A—C16A—H16B	110.1
C8—C9—H9A	118.7	N2—C16A—H16B	110.1
C9—C10—C11	121.0 (2)	H16A—C16A—H16B	108.4
C9—C10—H10A	119.5	N2—C16B—C17B	101.3 (8)
C11—C10—H10A	119.5	N2—C16B—H16C	111.5
N2—C11—C10	121.9 (2)	C17B—C16B—H16C	111.5
N2—C11—C12	121.6 (2)	N2—C16B—H16D	111.5
C10—C11—C12	116.4 (2)	C17B—C16B—H16D	111.5
C13—C12—C11	121.8 (2)	H16C—C16B—H16D	109.3
C13—C12—H12A	119.1	C16B—C17B—H17D	109.5
C11—C12—H12A	119.1	C16B—C17B—H17E	109.5
C12—C13—C8	121.6 (2)	H17D—C17B—H17E	109.5
C12—C13—H13A	119.2	C16B—C17B—H17F	109.5
C8—C13—H13A	119.2	H17D—C17B—H17F	109.5
N2—C14—C15	113.7 (2)	H17E—C17B—H17F	109.5
C5—N1—C1—C2	0.5 (3)	C11—C12—C13—C8	−0.4 (3)
C18—N1—C1—C2	−179.5 (2)	C9—C8—C13—C12	0.1 (3)
N1—C1—C2—C3	0.0 (3)	C7—C8—C13—C12	179.7 (2)
C1—C2—C3—C4	0.2 (4)	C11—N2—C14—C15	78.6 (3)
C2—C3—C4—C5	−0.9 (3)	C16B—N2—C14—C15	−70.2 (5)
C1—N1—C5—C4	−1.1 (3)	C16A—N2—C14—C15	−111.0 (4)
C18—N1—C5—C4	178.96 (19)	C24—C19—C20—C21	0.5 (4)
C1—N1—C5—C6	178.28 (18)	C19—C20—C21—C22	−0.7 (4)
C18—N1—C5—C6	−1.7 (3)	C19—C20—C21—Cl1	178.81 (18)
C3—C4—C5—N1	1.3 (3)	C20—C21—C22—C23	−0.1 (3)
C3—C4—C5—C6	−178.1 (2)	Cl1—C21—C22—C23	−179.58 (17)
N1—C5—C6—C7	−174.3 (2)	C21—C22—C23—C24	1.0 (3)
C4—C5—C6—C7	5.0 (3)	C20—C19—C24—C23	0.4 (3)
C5—C6—C7—C8	177.3 (2)	C20—C19—C24—S1	−177.73 (18)
C6—C7—C8—C13	−0.7 (4)	C22—C23—C24—C19	−1.2 (3)
C6—C7—C8—C9	178.9 (2)	C22—C23—C24—S1	177.00 (15)
C13—C8—C9—C10	−0.4 (3)	O3—S1—C24—C19	9.9 (2)
C7—C8—C9—C10	180.0 (2)	O1—S1—C24—C19	−110.69 (19)
C8—C9—C10—C11	0.9 (4)	O2—S1—C24—C19	130.60 (19)
C14—N2—C11—C10	8.5 (4)	O3—S1—C24—C23	−168.25 (16)
C16B—N2—C11—C10	155.2 (4)	O1—S1—C24—C23	71.18 (18)
C16A—N2—C11—C10	−161.5 (3)	O2—S1—C24—C23	−47.53 (19)
C14—N2—C11—C12	−173.5 (2)	C11—N2—C16A—C17A	−95.0 (4)
C16B—N2—C11—C12	−26.7 (5)	C14—N2—C16A—C17A	94.5 (4)
C16A—N2—C11—C12	16.5 (5)	C16B—N2—C16A—C17A	3.5 (5)
C9—C10—C11—N2	177.1 (2)	C11—N2—C16B—C17B	107.1 (5)
C9—C10—C11—C12	−1.1 (3)	C14—N2—C16B—C17B	−103.1 (5)
N2—C11—C12—C13	−177.3 (2)	C16A—N2—C16B—C17B	3.4 (5)
C10—C11—C12—C13	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···O1	0.81 (3)	1.98 (3)	2.783 (3)	174 (3)
O1W—H1W1···O2i	0.87 (3)	2.13 (4)	2.977 (3)	166 (3)
C2—H2A···O2ii	0.93	2.52	3.374 (3)	153
C4—H4A···O1Wiii	0.93	2.43	3.316 (3)	158
C13—H13A···O3	0.93	2.59	3.495 (3)	164
C18—H18A···O2iv	0.96	2.49	3.426 (3)	166
C18—H18C···O3	0.96	2.57	3.202 (3)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯O1	0.81 (3)	1.98 (3)	2.783 (3)	174 (3)
O1W—H1W1⋯O2i	0.87 (3)	2.13 (4)	2.977 (3)	166 (3)
C2—H2A⋯O2ii	0.93	2.52	3.374 (3)	153
C4—H4A⋯O1Wiii	0.93	2.43	3.316 (3)	158
C13—H13A⋯O3	0.93	2.59	3.495 (3)	164
C18—H18A⋯O2iv	0.96	2.49	3.426 (3)	166
C18—H18C⋯O3	0.96	2.57	3.202 (3)	123

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