2-{(E)-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-3H-indol-1-ium-2-yl]vin-yl}-6-hydroxy-meth-yl-4-nitro-phenolate dihydrate.

The title merocyanine-type mol-ecule, C(21)H(22)N(2)O(5)·2H(2)O, crystallizes in a zwitterionic form and has an E configuration at the styryl C=C bond. The styryl part of the mol-ecule and the indolium ring are slightly twisted and form a dihedral angle of 13.4 (1)°. The 1.274 (3) Å C-O bond length in the phenolate fragment is the longest among similar mol-ecules. Hydrogen bonds between solvent water mol-ecules, two hydroxyl groups and the phenolate O atom dictate the packing arrangement of mol-ecules in the crystal and join the mol-ecules into a two-dimensional polymeric network which propagates parallel to (001). Four water mol-ecules and four hydr-oxy groups form a centrosymmetric homodromic cyclic motif of O-H⋯O hydrogen bonds. Another cyclic centrosymmetric motif is generated by four water mol-ecules and two phenolate O atoms.

Related literature

This structure is similar to the perviously reported trans-MEH compound, see: Raymo et al. (2003 ▶). For similar structures, see also: Aldoshin & Atovmyan (1985 ▶), Hobley et al. (1999 ▶), Zou et al. (2003 ▶). For the synthetic procedure, see: Raymo & Giordani (2001 ▶).

Experimental

Crystal data

C21H22N2O5·2H2O

M = 418.44

Triclinic,

a = 7.377 (2) Å

b = 8.868 (2) Å

c = 16.817 (5) Å

α = 94.603 (5)°

β = 101.639 (6)°

γ = 102.140 (7)°

V = 1044.8 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 183 K

0.10 × 0.10 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.981, T max = 0.990

7525 measured reflections

3651 independent reflections

2472 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.134

S = 1.02

3651 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: XSHELL (Bruker, 2000 ▶); molecular graphics: XSHELL and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027238/gk2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027238/gk2221Isup2.hkl

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

C21H22N2O5·2H2O	Z = 2
Mr = 418.44	F(000) = 444
Triclinic, P1	Dx = 1.330 Mg m−3Dm = 1.31 (8) Mg m−3Dm measured by picnometer
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.377 (2) Å	Cell parameters from 200 reflections
b = 8.868 (2) Å	θ = 1–25°
c = 16.817 (5) Å	µ = 0.10 mm−1
α = 94.603 (5)°	T = 183 K
β = 101.639 (6)°	Block, dark red
γ = 102.140 (7)°	0.10 × 0.10 × 0.10 mm
V = 1044.8 (5) Å3

Bruker APEX CCD area-detector diffractometer	3651 independent reflections
Radiation source: fine-focus sealed tube	2472 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −8→8
Tmin = 0.981, Tmax = 0.990	k = −10→10
7525 measured reflections	l = −19→19

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0611P)2 + 0.0096P] where P = (Fo2 + 2Fc2)/3
3651 reflections	(Δ/σ)max < 0.001
271 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 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 > 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
N1	0.4314 (3)	0.7565 (2)	0.27176 (12)	0.0266 (5)
N2	−0.7317 (3)	0.3125 (2)	0.07265 (13)	0.0297 (5)
O1	0.3009 (3)	0.8842 (2)	0.40555 (12)	0.0453 (5)
H1	0.3172	0.9730	0.3903	0.054*
O2	−0.1195 (2)	0.4576 (2)	0.33751 (11)	0.0348 (5)
O3	−0.7048 (3)	0.3290 (2)	0.00334 (11)	0.0399 (5)
O4	−0.8914 (3)	0.2639 (2)	0.08513 (12)	0.0439 (6)
O5	−0.6302 (2)	0.1775 (2)	0.36144 (11)	0.0376 (5)
H5	−0.7015	0.2285	0.3787	0.045*
C1	0.5663 (3)	0.8684 (3)	0.24386 (15)	0.0275 (6)
C2	0.7509 (4)	0.9396 (3)	0.28370 (17)	0.0337 (7)
H2A	0.8074	0.9150	0.3355	0.040*
C3	0.8489 (4)	1.0488 (3)	0.24380 (18)	0.0392 (7)
H3	0.9755	1.1027	0.2694	0.047*
C4	0.7670 (4)	1.0812 (3)	0.16759 (18)	0.0381 (7)
H4	0.8380	1.1564	0.1416	0.046*
C5	0.5822 (4)	1.0052 (3)	0.12871 (17)	0.0331 (7)
H5A	0.5267	1.0267	0.0760	0.040*
C6	0.4804 (3)	0.8976 (3)	0.16797 (15)	0.0251 (6)
C7	0.2797 (3)	0.8003 (3)	0.14308 (14)	0.0248 (6)
C8	0.2563 (4)	0.6884 (3)	0.06505 (15)	0.0308 (6)
H8A	0.2692	0.7482	0.0192	0.046*
H8B	0.1302	0.6172	0.0529	0.046*
H8C	0.3545	0.6285	0.0734	0.046*
C9	0.1368 (4)	0.9048 (3)	0.12986 (17)	0.0355 (7)
H9A	0.1498	0.9716	0.1810	0.053*
H9B	0.0071	0.8398	0.1132	0.053*
H9C	0.1625	0.9697	0.0871	0.053*
C10	0.2648 (3)	0.7159 (3)	0.21803 (15)	0.0246 (6)
C11	0.4762 (4)	0.7097 (3)	0.35407 (15)	0.0311 (6)
H11A	0.6030	0.6851	0.3639	0.037*
H11B	0.3813	0.6147	0.3575	0.037*
C12	0.4755 (4)	0.8380 (3)	0.41955 (16)	0.0392 (7)
H12A	0.4980	0.8006	0.4738	0.047*
H12B	0.5804	0.9288	0.4203	0.047*
C13	0.1035 (3)	0.6165 (3)	0.23467 (15)	0.0274 (6)
H13	0.1166	0.5811	0.2869	0.033*
C14	−0.0685 (3)	0.5680 (3)	0.18168 (16)	0.0275 (6)
H14	−0.0760	0.5985	0.1284	0.033*
C15	−0.2409 (3)	0.4756 (3)	0.19654 (15)	0.0244 (6)
C16	−0.3992 (3)	0.4350 (3)	0.13128 (15)	0.0249 (6)
H16	−0.3883	0.4651	0.0792	0.030*
C17	−0.5708 (3)	0.3522 (3)	0.14124 (15)	0.0249 (6)
C18	−0.5931 (3)	0.3052 (3)	0.21741 (15)	0.0252 (6)
H18	−0.7142	0.2517	0.2237	0.030*
C19	−0.4402 (4)	0.3369 (3)	0.28191 (15)	0.0250 (6)
C20	−0.2575 (4)	0.4255 (3)	0.27503 (15)	0.0266 (6)
C21	−0.4511 (4)	0.2795 (3)	0.36328 (16)	0.0327 (7)
H21A	−0.3487	0.2240	0.3791	0.039*
H21B	−0.4292	0.3699	0.4054	0.039*
O10	0.9517 (3)	0.7347 (2)	0.43717 (12)	0.0471 (6)
H10A	1.0729	0.7979	0.4350	0.071*
H10B	0.9319	0.6349	0.4070	0.071*
O20	0.1635 (3)	0.3445 (3)	0.42365 (13)	0.0642 (7)
H20B	0.1048	0.3071	0.4659	0.096*
H20A	0.0628	0.3721	0.3872	0.096*

	U11	U22	U33	U12	U13	U23
N1	0.0212 (12)	0.0303 (12)	0.0277 (12)	0.0033 (10)	0.0063 (10)	0.0044 (10)
N2	0.0267 (13)	0.0250 (12)	0.0348 (14)	−0.0003 (10)	0.0046 (11)	0.0106 (10)
O1	0.0443 (13)	0.0374 (12)	0.0578 (14)	0.0064 (10)	0.0235 (11)	0.0051 (10)
O2	0.0280 (11)	0.0442 (12)	0.0284 (10)	0.0022 (9)	0.0019 (9)	0.0099 (9)
O3	0.0369 (12)	0.0498 (13)	0.0275 (11)	−0.0016 (10)	0.0049 (9)	0.0094 (9)
O4	0.0216 (11)	0.0570 (13)	0.0477 (13)	−0.0046 (10)	0.0038 (9)	0.0221 (10)
O5	0.0340 (11)	0.0422 (12)	0.0401 (11)	0.0048 (9)	0.0168 (9)	0.0148 (9)
C1	0.0214 (14)	0.0312 (15)	0.0306 (15)	0.0028 (12)	0.0119 (12)	0.0014 (12)
C2	0.0203 (15)	0.0408 (17)	0.0372 (16)	0.0033 (13)	0.0063 (12)	−0.0003 (13)
C3	0.0215 (15)	0.0390 (17)	0.054 (2)	−0.0017 (13)	0.0140 (14)	−0.0045 (15)
C4	0.0347 (17)	0.0322 (16)	0.053 (2)	0.0054 (14)	0.0255 (15)	0.0068 (14)
C5	0.0342 (17)	0.0317 (16)	0.0372 (17)	0.0073 (13)	0.0163 (14)	0.0070 (13)
C6	0.0252 (14)	0.0232 (14)	0.0272 (14)	0.0053 (11)	0.0081 (12)	−0.0006 (11)
C7	0.0238 (14)	0.0268 (14)	0.0245 (14)	0.0064 (12)	0.0065 (11)	0.0030 (11)
C8	0.0326 (16)	0.0335 (16)	0.0275 (15)	0.0082 (13)	0.0086 (12)	0.0054 (12)
C9	0.0275 (16)	0.0291 (15)	0.0486 (18)	0.0047 (13)	0.0075 (13)	0.0042 (13)
C10	0.0209 (14)	0.0281 (14)	0.0245 (14)	0.0061 (12)	0.0054 (11)	−0.0003 (11)
C11	0.0268 (15)	0.0379 (16)	0.0270 (15)	0.0074 (13)	0.0009 (12)	0.0085 (13)
C12	0.0405 (18)	0.0474 (19)	0.0272 (15)	0.0073 (15)	0.0049 (14)	0.0047 (13)
C13	0.0238 (15)	0.0321 (15)	0.0242 (14)	0.0016 (12)	0.0041 (12)	0.0066 (11)
C14	0.0284 (15)	0.0276 (14)	0.0267 (14)	0.0038 (12)	0.0090 (12)	0.0035 (11)
C15	0.0225 (14)	0.0223 (13)	0.0293 (14)	0.0054 (11)	0.0073 (12)	0.0043 (11)
C16	0.0265 (15)	0.0230 (13)	0.0256 (14)	0.0028 (11)	0.0085 (12)	0.0074 (11)
C17	0.0214 (14)	0.0227 (13)	0.0284 (14)	0.0023 (11)	0.0031 (11)	0.0041 (11)
C18	0.0223 (14)	0.0221 (13)	0.0320 (15)	0.0027 (11)	0.0090 (12)	0.0065 (11)
C19	0.0271 (15)	0.0211 (13)	0.0286 (14)	0.0056 (11)	0.0091 (12)	0.0063 (11)
C20	0.0273 (15)	0.0247 (14)	0.0269 (15)	0.0056 (12)	0.0037 (12)	0.0036 (11)
C21	0.0298 (16)	0.0367 (16)	0.0316 (15)	0.0037 (13)	0.0090 (13)	0.0085 (13)
O10	0.0411 (12)	0.0499 (13)	0.0513 (13)	0.0091 (10)	0.0144 (10)	0.0054 (10)
O20	0.0526 (15)	0.104 (2)	0.0522 (14)	0.0420 (14)	0.0186 (12)	0.0250 (14)

N1—C10	1.331 (3)	C9—H9A	0.9797
N1—C1	1.429 (3)	C9—H9B	0.9799
N1—C11	1.471 (3)	C9—H9C	0.9803
N2—O4	1.232 (3)	C10—C13	1.416 (3)
N2—O3	1.236 (3)	C11—C12	1.520 (4)
N2—C17	1.439 (3)	C11—H11A	0.9895
O1—C12	1.414 (3)	C11—H11B	0.9895
O1—H1	0.8400	C12—H12A	0.9904
O2—C20	1.273 (3)	C12—H12B	0.9898
O5—C21	1.429 (3)	C13—C14	1.357 (3)
O5—H5	0.8405	C13—H13	0.9492
C1—C6	1.376 (3)	C14—C15	1.440 (3)
C1—C2	1.380 (3)	C14—H14	0.9503
C2—C3	1.385 (4)	C15—C16	1.393 (3)
C2—H2A	0.9507	C15—C20	1.446 (3)
C3—C4	1.382 (4)	C16—C17	1.373 (3)
C3—H3	0.9503	C16—H16	0.9504
C4—C5	1.387 (4)	C17—C18	1.408 (3)
C4—H4	0.9500	C18—C19	1.361 (3)
C5—C6	1.382 (3)	C18—H18	0.9499
C5—H5A	0.9502	C19—C20	1.442 (3)
C6—C7	1.506 (3)	C19—C21	1.509 (3)
C7—C10	1.527 (3)	C21—H21A	0.9901
C7—C8	1.538 (3)	C21—H21B	0.9898
C7—C9	1.539 (3)	O10—H10A	0.9594
C8—H8A	0.9795	O10—H10B	0.9515
C8—H8B	0.9805	O20—H20B	0.9502
C8—H8C	0.9795	O20—H20A	0.9513
C10—N1—C1	111.6 (2)	C13—C10—C7	128.7 (2)
C10—N1—C11	127.0 (2)	N1—C11—C12	111.2 (2)
C1—N1—C11	121.1 (2)	N1—C11—H11A	109.4
O4—N2—O3	122.4 (2)	C12—C11—H11A	109.4
O4—N2—C17	118.9 (2)	N1—C11—H11B	109.4
O3—N2—C17	118.8 (2)	C12—C11—H11B	109.4
C12—O1—H1	109.4	H11A—C11—H11B	108.0
C21—O5—H5	109.4	O1—C12—C11	111.7 (2)
C6—C1—C2	123.8 (2)	O1—C12—H12A	109.2
C6—C1—N1	108.1 (2)	C11—C12—H12A	109.3
C2—C1—N1	128.0 (2)	O1—C12—H12B	109.3
C1—C2—C3	116.1 (3)	C11—C12—H12B	109.3
C1—C2—H2A	121.9	H12A—C12—H12B	108.0
C3—C2—H2A	122.0	C14—C13—C10	125.0 (2)
C4—C3—C2	121.5 (3)	C14—C13—H13	117.5
C4—C3—H3	119.2	C10—C13—H13	117.5
C2—C3—H3	119.2	C13—C14—C15	127.7 (2)
C3—C4—C5	120.7 (3)	C13—C14—H14	116.1
C3—C4—H4	119.6	C15—C14—H14	116.2
C5—C4—H4	119.7	C16—C15—C14	117.3 (2)
C6—C5—C4	118.8 (3)	C16—C15—C20	119.2 (2)
C6—C5—H5A	120.6	C14—C15—C20	123.5 (2)
C4—C5—H5A	120.6	C17—C16—C15	120.9 (2)
C1—C6—C5	119.0 (2)	C17—C16—H16	119.5
C1—C6—C7	109.7 (2)	C15—C16—H16	119.6
C5—C6—C7	131.3 (2)	C16—C17—C18	121.4 (2)
C6—C7—C10	101.47 (19)	C16—C17—N2	119.5 (2)
C6—C7—C8	110.0 (2)	C18—C17—N2	119.1 (2)
C10—C7—C8	112.7 (2)	C19—C18—C17	119.7 (2)
C6—C7—C9	110.5 (2)	C19—C18—H18	120.2
C10—C7—C9	111.1 (2)	C17—C18—H18	120.2
C8—C7—C9	110.8 (2)	C18—C19—C20	121.1 (2)
C7—C8—H8A	109.4	C18—C19—C21	122.3 (2)
C7—C8—H8B	109.5	C20—C19—C21	116.6 (2)
H8A—C8—H8B	109.5	O2—C20—C19	119.4 (2)
C7—C8—H8C	109.5	O2—C20—C15	122.9 (2)
H8A—C8—H8C	109.5	C19—C20—C15	117.7 (2)
H8B—C8—H8C	109.5	O5—C21—C19	112.6 (2)
C7—C9—H9A	109.5	O5—C21—H21A	109.0
C7—C9—H9B	109.5	C19—C21—H21A	109.1
H9A—C9—H9B	109.4	O5—C21—H21B	109.1
C7—C9—H9C	109.5	C19—C21—H21B	109.1
H9A—C9—H9C	109.4	H21A—C21—H21B	107.8
H9B—C9—H9C	109.5	H10A—O10—H10B	110.1
N1—C10—C13	122.2 (2)	H20B—O20—H20A	102.9
N1—C10—C7	109.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20B···O10i	0.96	1.80	2.739 (4)	166
O10—H10B···O2ii	0.95	1.81	2.750 (3)	172
O20—H20A···O2	0.95	1.78	2.714 (3)	167
O10—H10A···O1ii	0.95	1.87	2.811 (3)	165
O5—H5···O20iii	0.84	1.80	2.633 (3)	175
O1—H1···O5iv	0.84	1.90	2.734 (3)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O20—H20B⋯O10i	0.96	1.80	2.739 (4)	166
O10—H10B⋯O2ii	0.95	1.81	2.750 (3)	172
O20—H20A⋯O2	0.95	1.78	2.714 (3)	167
O10—H10A⋯O1ii	0.95	1.87	2.811 (3)	165
O5—H5⋯O20iii	0.84	1.80	2.633 (3)	175
O1—H1⋯O5iv	0.84	1.90	2.734 (3)	176

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