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

In the cation of the title compound, C(18)H(23)N(2) (+)·C(7)H(7)O(4)S(-)·H(2)O, one ethyl group of the diethyl-amino unit is disordered over two sets of sites in a 0.665 (6):0.335 (6) ratio. The styrylpyridinium unit is nearly planar, with a dihedral angle between the pyridinium and benzene rings of 4.27 (8)°. In the crystal, the anion ring is almost perpendicular to the aromatic rings of the cation; the sulfonate-substituted benzene ring forms dihedral angles of 89.60 (8) and 89.37 (8)°, respectively, with the pyridinium and benzene rings of the cation. In the crystal, the three components are linked into a three-dimensional network by O-H⋯O and C-H⋯O hydrogen bonds. π-π inter-actions with centroid-centroid distances of 3.6999 (9) and 3.7106 (9) Å are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to and applications of quaternary ammonium compounds, see: Chanawanno et al. (2010 ▶); Domagk (1935 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶); Kaewmanee et al. (2010 ▶).

Experimental

Crystal data

C18H23N2 +·C7H7O4S−·H2O

M = 472.60

Triclinic,

a = 7.4430 (2) Å

b = 10.3298 (2) Å

c = 16.3817 (4) Å

α = 91.265 (1)°

β = 100.794 (1)°

γ = 102.281 (1)°

V = 1206.39 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.17 mm−1

T = 298 K

0.53 × 0.19 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.914, T max = 0.978

28598 measured reflections

6988 independent reflections

4465 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.145

S = 1.06

6988 reflections

312 parameters

H-atom parameters constrained

Δρmax = 0.29 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/S1600536812035258/is5179sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035258/is5179Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035258/is5179Isup3.cml

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

C18H23N2+·C7H7O4S−·H2O	Z = 2
Mr = 472.60	F(000) = 504
Triclinic, P1	Dx = 1.301 Mg m−3
Hall symbol: -P 1	Melting point = 421–423 K
a = 7.4430 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3298 (2) Å	Cell parameters from 6988 reflections
c = 16.3817 (4) Å	θ = 2.0–30.0°
α = 91.265 (1)°	µ = 0.17 mm−1
β = 100.794 (1)°	T = 298 K
γ = 102.281 (1)°	Needle, orange
V = 1206.39 (5) Å3	0.53 × 0.19 × 0.13 mm

Bruker APEXII CCD area-detector diffractometer	6988 independent reflections
Radiation source: sealed tube	4465 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 30.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.914, Tmax = 0.978	k = −14→14
28598 measured reflections	l = −23→23

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.1741P] where P = (Fo2 + 2Fc2)/3
6988 reflections	(Δ/σ)max = 0.001
312 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.32 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	−0.50562 (17)	1.00872 (12)	0.61471 (8)	0.0443 (3)
N2	0.6382 (2)	0.95002 (15)	0.87724 (11)	0.0724 (5)
C1	−0.6858 (2)	0.98155 (17)	0.57237 (10)	0.0522 (4)
H1A	−0.7540	1.0476	0.5693	0.063*
C2	−0.7688 (2)	0.85902 (18)	0.53425 (11)	0.0594 (4)
H2A	−0.8923	0.8413	0.5053	0.071*
C3	−0.6657 (3)	0.76154 (18)	0.53944 (11)	0.0615 (5)
H3A	−0.7199	0.6772	0.5142	0.074*
C4	−0.4839 (2)	0.78983 (16)	0.58190 (11)	0.0548 (4)
H4A	−0.4149	0.7243	0.5845	0.066*
C5	−0.3994 (2)	0.91516 (15)	0.62153 (9)	0.0448 (3)
C6	−0.2092 (2)	0.94942 (16)	0.66919 (10)	0.0499 (4)
H6A	−0.1625	1.0363	0.6914	0.060*
C7	−0.0969 (2)	0.86422 (16)	0.68320 (10)	0.0494 (4)
H7A	−0.1447	0.7789	0.6583	0.059*
C8	0.0914 (2)	0.88967 (15)	0.73292 (9)	0.0456 (3)
C9	0.1915 (2)	0.78913 (16)	0.74038 (10)	0.0508 (4)
H9A	0.1356	0.7070	0.7124	0.061*
C10	0.3691 (2)	0.80681 (16)	0.78742 (11)	0.0524 (4)
H10A	0.4304	0.7369	0.7907	0.063*
C11	0.4595 (2)	0.92947 (16)	0.83076 (10)	0.0509 (4)
C12	0.3604 (2)	1.03119 (16)	0.82244 (10)	0.0519 (4)
H12A	0.4165	1.1138	0.8498	0.062*
C13	0.1826 (2)	1.01232 (16)	0.77504 (10)	0.0495 (4)
H13A	0.1217	1.0824	0.7709	0.059*
C16	0.7364 (3)	0.84251 (19)	0.89166 (13)	0.0641 (5)
H16A	0.8703	0.8796	0.9060	0.077*
H16B	0.7119	0.7867	0.8407	0.077*
C17	0.6778 (3)	0.7585 (2)	0.96027 (14)	0.0828 (6)
H17A	0.7471	0.6898	0.9679	0.124*
H17B	0.5461	0.7192	0.9456	0.124*
H17C	0.7029	0.8131	1.0111	0.124*
C18	−0.4297 (2)	1.14455 (15)	0.65430 (11)	0.0539 (4)
H18A	−0.5196	1.1983	0.6384	0.081*
H18B	−0.3154	1.1828	0.6364	0.081*
H18C	−0.4050	1.1406	0.7137	0.081*
S1	0.85883 (5)	0.64249 (4)	0.33983 (3)	0.05481 (14)
O1	0.14269 (17)	0.50219 (14)	0.09686 (8)	0.0711 (4)
O2	0.8984 (2)	0.52093 (14)	0.37195 (11)	0.0983 (6)
O3	0.8267 (2)	0.72821 (16)	0.40326 (10)	0.0928 (5)
O4	0.99412 (18)	0.70754 (16)	0.29340 (10)	0.0853 (4)
C19	0.6343 (2)	0.61781 (16)	0.18441 (11)	0.0535 (4)
H19A	0.7427	0.6557	0.1655	0.064*
C20	0.4652 (2)	0.58362 (18)	0.12927 (11)	0.0591 (4)
H20A	0.4600	0.5972	0.0730	0.071*
C21	0.3033 (2)	0.52931 (16)	0.15715 (10)	0.0518 (4)
C22	0.3100 (2)	0.50668 (16)	0.24013 (11)	0.0528 (4)
H22A	0.2010	0.4699	0.2590	0.063*
C23	0.4813 (2)	0.53940 (15)	0.29535 (10)	0.0504 (4)
H23A	0.4871	0.5232	0.3513	0.061*
C24	0.6431 (2)	0.59581 (14)	0.26792 (10)	0.0446 (3)
C25	−0.0281 (3)	0.4442 (3)	0.12097 (15)	0.0874 (7)
H25A	−0.1299	0.4370	0.0742	0.131*
H25B	−0.0474	0.4989	0.1653	0.131*
H25C	−0.0228	0.3575	0.1397	0.131*
C14A	0.7158 (4)	1.0661 (3)	0.9384 (2)	0.0620 (10)	0.665 (7)
H14A	0.7805	1.0379	0.9897	0.074*	0.665 (7)
H14B	0.6145	1.1036	0.9511	0.074*	0.665 (7)
C15A	0.8500 (5)	1.1693 (4)	0.9030 (2)	0.0837 (13)	0.665 (7)
H15A	0.9023	1.2430	0.9433	0.126*	0.665 (7)
H15B	0.7844	1.1994	0.8534	0.126*	0.665 (7)
H15C	0.9489	1.1314	0.8897	0.126*	0.665 (7)
C14B	0.7614 (10)	1.0907 (7)	0.8914 (5)	0.067 (2)*	0.335 (7)
H14C	0.8900	1.0911	0.8876	0.080*	0.335 (7)
H14D	0.7132	1.1497	0.8520	0.080*	0.335 (7)
C15B	0.7461 (11)	1.1271 (9)	0.9771 (5)	0.085 (3)*	0.335 (7)
H15D	0.8186	1.2155	0.9935	0.127*	0.335 (7)
H15E	0.7928	1.0661	1.0144	0.127*	0.335 (7)
H15F	0.6171	1.1235	0.9792	0.127*	0.335 (7)
O1W	0.2163 (2)	0.42954 (15)	0.44206 (9)	0.0802 (4)
H1W1	0.2043	0.4060	0.4991	0.096*
H2W1	0.1179	0.4626	0.4195	0.096*

	U11	U22	U33	U12	U13	U23
N1	0.0394 (6)	0.0452 (7)	0.0455 (7)	0.0056 (5)	0.0063 (5)	−0.0013 (5)
N2	0.0520 (8)	0.0551 (9)	0.1020 (13)	0.0181 (7)	−0.0109 (8)	−0.0106 (8)
C1	0.0411 (8)	0.0600 (10)	0.0536 (9)	0.0101 (7)	0.0061 (7)	0.0001 (7)
C2	0.0443 (8)	0.0672 (11)	0.0569 (10)	−0.0012 (8)	0.0018 (7)	−0.0034 (8)
C3	0.0620 (10)	0.0512 (9)	0.0599 (10)	−0.0032 (8)	0.0026 (8)	−0.0072 (8)
C4	0.0582 (10)	0.0439 (8)	0.0582 (10)	0.0074 (7)	0.0058 (8)	−0.0013 (7)
C5	0.0455 (8)	0.0422 (8)	0.0448 (8)	0.0067 (6)	0.0077 (6)	0.0019 (6)
C6	0.0454 (8)	0.0453 (8)	0.0545 (9)	0.0070 (6)	0.0030 (7)	−0.0030 (7)
C7	0.0493 (8)	0.0469 (8)	0.0503 (9)	0.0100 (7)	0.0065 (7)	0.0004 (7)
C8	0.0467 (8)	0.0449 (8)	0.0455 (8)	0.0107 (6)	0.0094 (6)	0.0032 (6)
C9	0.0533 (9)	0.0422 (8)	0.0555 (9)	0.0112 (7)	0.0067 (7)	−0.0010 (7)
C10	0.0536 (9)	0.0443 (8)	0.0622 (10)	0.0186 (7)	0.0093 (8)	0.0029 (7)
C11	0.0447 (8)	0.0494 (9)	0.0579 (9)	0.0128 (7)	0.0063 (7)	0.0016 (7)
C12	0.0520 (9)	0.0432 (8)	0.0587 (10)	0.0127 (7)	0.0049 (7)	−0.0048 (7)
C13	0.0509 (9)	0.0452 (8)	0.0545 (9)	0.0169 (7)	0.0086 (7)	0.0007 (7)
C16	0.0504 (9)	0.0674 (11)	0.0759 (12)	0.0243 (8)	0.0039 (9)	−0.0013 (9)
C17	0.0948 (16)	0.0816 (14)	0.0772 (14)	0.0340 (12)	0.0137 (12)	0.0032 (11)
C18	0.0488 (9)	0.0458 (8)	0.0636 (10)	0.0095 (7)	0.0048 (7)	−0.0107 (7)
S1	0.0428 (2)	0.0440 (2)	0.0716 (3)	0.01129 (16)	−0.00529 (19)	−0.00146 (19)
O1	0.0525 (7)	0.0869 (9)	0.0627 (8)	0.0079 (6)	−0.0074 (6)	0.0003 (7)
O2	0.0759 (10)	0.0629 (9)	0.1366 (14)	0.0167 (7)	−0.0315 (9)	0.0240 (9)
O3	0.0668 (9)	0.1074 (12)	0.0924 (11)	0.0314 (8)	−0.0219 (8)	−0.0470 (9)
O4	0.0450 (7)	0.0923 (10)	0.1062 (11)	−0.0044 (7)	0.0055 (7)	0.0094 (9)
C19	0.0482 (8)	0.0485 (9)	0.0628 (10)	0.0058 (7)	0.0137 (7)	0.0038 (7)
C20	0.0594 (10)	0.0637 (11)	0.0501 (9)	0.0069 (8)	0.0076 (8)	0.0069 (8)
C21	0.0463 (8)	0.0493 (9)	0.0555 (10)	0.0103 (7)	0.0003 (7)	−0.0018 (7)
C22	0.0433 (8)	0.0525 (9)	0.0596 (10)	0.0041 (7)	0.0105 (7)	−0.0003 (7)
C23	0.0511 (9)	0.0469 (8)	0.0501 (9)	0.0073 (7)	0.0062 (7)	0.0016 (7)
C24	0.0421 (7)	0.0345 (7)	0.0547 (9)	0.0092 (6)	0.0030 (6)	−0.0014 (6)
C25	0.0442 (10)	0.1211 (19)	0.0871 (15)	0.0093 (11)	0.0008 (10)	−0.0126 (14)
C14A	0.0534 (16)	0.0638 (18)	0.064 (2)	0.0186 (13)	−0.0045 (14)	−0.0106 (15)
C15A	0.079 (2)	0.060 (2)	0.096 (3)	−0.0026 (17)	0.0013 (18)	−0.0063 (17)
O1W	0.0792 (9)	0.0933 (10)	0.0774 (9)	0.0416 (8)	0.0134 (7)	0.0030 (8)

N1—C1	1.3572 (19)	C18—H18A	0.9600
N1—C5	1.367 (2)	C18—H18B	0.9600
N1—C18	1.4811 (19)	C18—H18C	0.9600
N2—C11	1.374 (2)	S1—O3	1.4364 (15)
N2—C16	1.454 (2)	S1—O4	1.4372 (15)
N2—C14A	1.487 (4)	S1—O2	1.4383 (14)
N2—C14B	1.531 (8)	S1—C24	1.7706 (15)
C1—C2	1.364 (2)	O1—C21	1.3732 (19)
C1—H1A	0.9300	O1—C25	1.416 (2)
C2—C3	1.385 (3)	C19—C20	1.377 (2)
C2—H2A	0.9300	C19—C24	1.383 (2)
C3—C4	1.368 (2)	C19—H19A	0.9300
C3—H3A	0.9300	C20—C21	1.380 (2)
C4—C5	1.399 (2)	C20—H20A	0.9300
C4—H4A	0.9300	C21—C22	1.378 (2)
C5—C6	1.449 (2)	C22—C23	1.389 (2)
C6—C7	1.332 (2)	C22—H22A	0.9300
C6—H6A	0.9300	C23—C24	1.381 (2)
C7—C8	1.450 (2)	C23—H23A	0.9300
C7—H7A	0.9300	C25—H25A	0.9600
C8—C9	1.396 (2)	C25—H25B	0.9600
C8—C13	1.401 (2)	C25—H25C	0.9600
C9—C10	1.373 (2)	C14A—C15A	1.504 (6)
C9—H9A	0.9300	C14A—H14A	0.9700
C10—C11	1.407 (2)	C14A—H14B	0.9700
C10—H10A	0.9300	C15A—H15A	0.9600
C11—C12	1.402 (2)	C15A—H15B	0.9600
C12—C13	1.375 (2)	C15A—H15C	0.9600
C12—H12A	0.9300	C14B—C15B	1.477 (12)
C13—H13A	0.9300	C14B—H14C	0.9700
C16—C17	1.507 (3)	C14B—H14D	0.9700
C16—H16A	0.9700	C15B—H15D	0.9600
C16—H16B	0.9700	C15B—H15E	0.9600
C17—H17A	0.9600	C15B—H15F	0.9600
C17—H17B	0.9600	O1W—H1W1	0.9855
C17—H17C	0.9600	O1W—H2W1	0.8948
C1—N1—C5	121.85 (13)	H17B—C17—H17C	109.5
C1—N1—C18	116.77 (13)	N1—C18—H18A	109.5
C5—N1—C18	121.38 (12)	N1—C18—H18B	109.5
C11—N2—C16	121.76 (14)	H18A—C18—H18B	109.5
C11—N2—C14A	121.37 (16)	N1—C18—H18C	109.5
C16—N2—C14A	113.64 (17)	H18A—C18—H18C	109.5
C11—N2—C14B	119.6 (3)	H18B—C18—H18C	109.5
C16—N2—C14B	115.9 (3)	O3—S1—O4	113.46 (10)
N1—C1—C2	121.17 (16)	O3—S1—O2	111.88 (11)
N1—C1—H1A	119.4	O4—S1—O2	112.97 (10)
C2—C1—H1A	119.4	O3—S1—C24	105.87 (8)
C1—C2—C3	118.79 (16)	O4—S1—C24	106.18 (8)
C1—C2—H2A	120.6	O2—S1—C24	105.71 (8)
C3—C2—H2A	120.6	C21—O1—C25	117.97 (15)
C4—C3—C2	119.71 (15)	C20—C19—C24	120.06 (15)
C4—C3—H3A	120.1	C20—C19—H19A	120.0
C2—C3—H3A	120.1	C24—C19—H19A	120.0
C3—C4—C5	121.47 (16)	C19—C20—C21	120.26 (16)
C3—C4—H4A	119.3	C19—C20—H20A	119.9
C5—C4—H4A	119.3	C21—C20—H20A	119.9
N1—C5—C4	117.00 (14)	O1—C21—C22	124.66 (15)
N1—C5—C6	119.21 (13)	O1—C21—C20	115.03 (15)
C4—C5—C6	123.79 (15)	C22—C21—C20	120.31 (15)
C7—C6—C5	124.12 (14)	C21—C22—C23	119.25 (15)
C7—C6—H6A	117.9	C21—C22—H22A	120.4
C5—C6—H6A	117.9	C23—C22—H22A	120.4
C6—C7—C8	127.23 (15)	C24—C23—C22	120.60 (15)
C6—C7—H7A	116.4	C24—C23—H23A	119.7
C8—C7—H7A	116.4	C22—C23—H23A	119.7
C9—C8—C13	116.61 (14)	C23—C24—C19	119.50 (14)
C9—C8—C7	119.95 (14)	C23—C24—S1	119.97 (12)
C13—C8—C7	123.44 (14)	C19—C24—S1	120.51 (12)
C10—C9—C8	122.58 (14)	O1—C25—H25A	109.5
C10—C9—H9A	118.7	O1—C25—H25B	109.5
C8—C9—H9A	118.7	H25A—C25—H25B	109.5
C9—C10—C11	120.76 (15)	O1—C25—H25C	109.5
C9—C10—H10A	119.6	H25A—C25—H25C	109.5
C11—C10—H10A	119.6	H25B—C25—H25C	109.5
N2—C11—C12	121.41 (14)	N2—C14A—C15A	109.7 (3)
N2—C11—C10	121.78 (15)	N2—C14A—H14A	109.7
C12—C11—C10	116.78 (14)	C15A—C14A—H14A	109.7
C13—C12—C11	121.91 (14)	N2—C14A—H14B	109.7
C13—C12—H12A	119.0	C15A—C14A—H14B	109.7
C11—C12—H12A	119.0	H14A—C14A—H14B	108.2
C12—C13—C8	121.35 (14)	C15B—C14B—N2	101.4 (6)
C12—C13—H13A	119.3	C15B—C14B—H14C	111.5
C8—C13—H13A	119.3	N2—C14B—H14C	111.5
N2—C16—C17	112.53 (17)	C15B—C14B—H14D	111.5
N2—C16—H16A	109.1	N2—C14B—H14D	111.5
C17—C16—H16A	109.1	H14C—C14B—H14D	109.3
N2—C16—H16B	109.1	C14B—C15B—H15D	109.5
C17—C16—H16B	109.1	C14B—C15B—H15E	109.5
H16A—C16—H16B	107.8	H15D—C15B—H15E	109.5
C16—C17—H17A	109.5	C14B—C15B—H15F	109.5
C16—C17—H17B	109.5	H15D—C15B—H15F	109.5
H17A—C17—H17B	109.5	H15E—C15B—H15F	109.5
C16—C17—H17C	109.5	H1W1—O1W—H2W1	108.6
H17A—C17—H17C	109.5
C5—N1—C1—C2	−0.3 (2)	C9—C8—C13—C12	−1.2 (2)
C18—N1—C1—C2	−179.54 (15)	C7—C8—C13—C12	179.05 (15)
N1—C1—C2—C3	0.1 (3)	C11—N2—C16—C17	−80.5 (2)
C1—C2—C3—C4	−0.4 (3)	C14A—N2—C16—C17	79.5 (3)
C2—C3—C4—C5	0.9 (3)	C14B—N2—C16—C17	118.5 (4)
C1—N1—C5—C4	0.8 (2)	C24—C19—C20—C21	1.1 (3)
C18—N1—C5—C4	179.99 (14)	C25—O1—C21—C22	−1.4 (3)
C1—N1—C5—C6	−178.59 (14)	C25—O1—C21—C20	178.95 (18)
C18—N1—C5—C6	0.6 (2)	C19—C20—C21—O1	178.51 (15)
C3—C4—C5—N1	−1.1 (2)	C19—C20—C21—C22	−1.1 (3)
C3—C4—C5—C6	178.25 (16)	O1—C21—C22—C23	−179.48 (15)
N1—C5—C6—C7	176.57 (15)	C20—C21—C22—C23	0.1 (3)
C4—C5—C6—C7	−2.8 (3)	C21—C22—C23—C24	0.9 (2)
C5—C6—C7—C8	−177.25 (15)	C22—C23—C24—C19	−1.0 (2)
C6—C7—C8—C9	−179.16 (16)	C22—C23—C24—S1	177.67 (12)
C6—C7—C8—C13	0.6 (3)	C20—C19—C24—C23	0.0 (2)
C13—C8—C9—C10	1.1 (2)	C20—C19—C24—S1	−178.67 (13)
C7—C8—C9—C10	−179.14 (15)	O3—S1—C24—C23	−54.23 (15)
C8—C9—C10—C11	−0.1 (3)	O4—S1—C24—C23	−175.13 (13)
C16—N2—C11—C12	175.03 (17)	O2—S1—C24—C23	64.62 (15)
C14A—N2—C11—C12	16.6 (3)	O3—S1—C24—C19	124.45 (15)
C14B—N2—C11—C12	−24.6 (4)	O4—S1—C24—C19	3.56 (16)
C16—N2—C11—C10	−6.8 (3)	O2—S1—C24—C19	−116.70 (15)
C14A—N2—C11—C10	−165.2 (2)	C11—N2—C14A—C15A	−103.6 (3)
C14B—N2—C11—C10	153.6 (4)	C16—N2—C14A—C15A	96.4 (3)
C9—C10—C11—N2	−179.06 (17)	C14B—N2—C14A—C15A	−5.6 (5)
C9—C10—C11—C12	−0.8 (3)	C11—N2—C14B—C15B	101.7 (5)
N2—C11—C12—C13	178.98 (17)	C16—N2—C14B—C15B	−96.8 (5)
C10—C11—C12—C13	0.7 (3)	C14A—N2—C14B—C15B	−1.8 (4)
C11—C12—C13—C8	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2i	0.99	2.53	3.371 (2)	143
O1W—H1W1···O3i	0.99	2.15	3.073 (2)	155
O1W—H2W1···O2ii	0.89	1.90	2.791 (2)	176
C1—H1A···O3iii	0.93	2.54	3.419 (2)	158
C2—H2A···O3iv	0.93	2.47	3.349 (2)	158
C4—H4A···O1Wv	0.93	2.47	3.381 (2)	166
C7—H7A···O1Wv	0.93	2.58	3.479 (2)	163
C17—H17A···O1i	0.96	2.58	3.435 (3)	149
C18—H18A···O3iii	0.96	2.54	3.466 (2)	162
C18—H18B···O4vi	0.96	2.47	3.221 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2i	0.99	2.53	3.371 (2)	143
O1W—H1W1⋯O3i	0.99	2.15	3.073 (2)	155
O1W—H2W1⋯O2ii	0.89	1.90	2.791 (2)	176
C1—H1A⋯O3iii	0.93	2.54	3.419 (2)	158
C2—H2A⋯O3iv	0.93	2.47	3.349 (2)	158
C4—H4A⋯O1W v	0.93	2.47	3.381 (2)	166
C7—H7A⋯O1W v	0.93	2.58	3.479 (2)	163
C17—H17A⋯O1i	0.96	2.58	3.435 (3)	149
C18—H18A⋯O3iii	0.96	2.54	3.466 (2)	162
C18—H18B⋯O4vi	0.96	2.47	3.221 (2)	135

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