(E)-Ethyl 2-cyano-3-[4-(4,5-diphenyl-1H-imidazol-2-yl)phen­yl]acrylate dihydrate

Liao, W.-X.; Peng, Y.-W.; Yu, L.; Ning, X.-Q.; Zeng, H.-P.

doi:10.1107/S1600536811006039

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o707

doi:10.1107/S1600536811006039

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(E)-Ethyl 2-cyano-3-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl]acrylate dihydrate

Wei-Xing Liao,^a Yi-Wen Peng,^a Li Yu,^a Xiao-Qing Ning ^a and He-Ping Zeng ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: zenghp@scnu.edu.cn

(Received 21 November 2010; accepted 17 February 2011; online 26 February 2011)

In the title compound, C₂₇H₂₁N₃O₂·2H₂O, the three benzene rings attached to the heterocyclic imidazole ring are not coplanar with the latter, making dihedral angles of 14.8 (2), 31.4 (2), and 37.5 (2)°, respectively, for the benzene ring planes in the 2-, 4- and 5-positions. In the crystal, there are two water molecules which serve as connectors between the acrylate molecules and stabilize the structure via N—H⋯O, O—H⋯N, C—H⋯O and O—H⋯O hydrogen bonding.

Related literature

For background to the electronic and photophysical properties of 2,4,5-triarylimidazoles, see: Valiyev et al. (2007 ). For the synthetic procedure, see: Liu et al. (2006 ). For related structures, see: Fridman et al. (2009 ).

Experimental

Crystal data

C₂₇H₂₁N₃O₂·2H₂O
M_r = 455.50
Triclinic, $[P \overline 1]$
a = 8.4976 (16) Å
b = 9.0263 (17) Å
c = 16.421 (3) Å
α = 83.536 (2)°
β = 79.821 (2)°
γ = 71.089 (2)°
V = 1170.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.28 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.962, T_max = 0.969
5922 measured reflections
4048 independent reflections
3010 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.134
S = 1.03
4048 reflections
326 parameters
9 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1W	0.88 (3)	2.04 (3)	2.915 (3)	172 (2)
O2W—H3W⋯N2	0.89 (4)	1.98 (4)	2.870 (3)	173 (3)
C9—H9⋯O1W	0.93	2.48	3.338 (3)	154
O1W—H2W⋯O2Wⁱ	0.86 (4)	1.95 (2)	2.789 (3)	165 (4)
O1W—H1W⋯N3ⁱⁱ	0.83 (2)	2.24 (2)	3.034 (3)	159 (3)
O2W—H4W⋯O1Wⁱⁱⁱ	0.81 (4)	2.25 (4)	3.041 (4)	167 (4)
Symmetry codes: (i) x, y+1, z; (ii) -x, -y+2, -z+1; (iii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006039/pv2361sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006039/pv2361Isup2.hkl

checkCIF report

Comment top

2,4,5-Triarylimidazoles based on extended organic π systems have received increasing interest due to the intriguing electronic and photophysical properties (Valiyev et al., 2007). As part of our on-going research interest in chemiluminescence compounds, the title compound was synthesized and its crystal structure determined as described herein.

The molecular structure of the title compound is presented in Fig. 1. Three benzene rings attached to the heterocyclic imidazole ring are not coplanar with the latter, with dihedral angles of 14.8 (2)°, 31.4 (2)°, and 37.5 (2)°, respectively, between the benzene ring planes in the 2-, 4- and 5-positions of the imidazole ring.

In the crystal packing, H₂O molecules serve as connectors to form the three-dimensional packing via hydrogen bonds (Fig. 2, Tab. 1), including N—H···O, O—H···N, C—H···O and O—H···O hydrogen bonds.

The crystal structures of several compounds related to the title molecule have been reported (Fridman et al., 2009).

Related literature top

For background to the electronic and photophysical properties of 2,4,5-triarylimidazoles, see: Valiyev et al. (2007). For the synthetic procedure, see: Liu et al. (2006). For related structures, see: Fridman et al. (2009).

Experimental top

The title compound was prepared as reported earlier (Liu et al., 2006). A mixture of 4-(4,5-diphenyl-1H-imidazol-2-yl)benzaldehyde (0.225 g, 0.69 mmol), ethyl 2-cyanoacetate (0.156 g, 2.1 mmol) and pyridine (2 ml) was stirred at room temperature for 10 h. The solution was poured into water (15 ml) and orange precipitate of the title compound formed immediately. The precipitate obtained was filtered, washed with water and dried. Single crystals of the title compound were obtained by slow evaporation from ethyl acetate at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme and 50% probability Displacement ellipsoids.
	Fig. 2. Part view of the crystal structure, showing hydrogen bonds indicated by dashed lines. Hydrogen atoms not involved in H-bonds have been omitted for clarity.

(E)-Ethyl 2-cyano-3-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl]acrylate dihydrate top

Crystal data top

C₂₇H₂₁N₃O₂·2H₂O	Z = 2
M_r = 455.50	F(000) = 480
Triclinic, P1	D_x = 1.292 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4976 (16) Å	Cell parameters from 2029 reflections
b = 9.0263 (17) Å	θ = 2.4–24.2°
c = 16.421 (3) Å	µ = 0.09 mm⁻¹
α = 83.536 (2)°	T = 296 K
β = 79.821 (2)°	Block, red
γ = 71.089 (2)°	0.30 × 0.28 × 0.24 mm
V = 1170.7 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	4048 independent reflections
Radiation source: fine-focus sealed tube	3010 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
T_min = 0.962, T_max = 0.969	k = −10→5
5922 measured reflections	l = −18→19

Refinement top

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.057P)² + 0.3479P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4048 reflections	Δρ_max = 0.31 e Å⁻³
326 parameters	Δρ_min = −0.28 e Å⁻³
9 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.049 (4)

Crystal data top

C₂₇H₂₁N₃O₂·2H₂O	γ = 71.089 (2)°
M_r = 455.50	V = 1170.7 (4) Å³
Triclinic, P1	Z = 2
a = 8.4976 (16) Å	Mo Kα radiation
b = 9.0263 (17) Å	µ = 0.09 mm⁻¹
c = 16.421 (3) Å	T = 296 K
α = 83.536 (2)°	0.30 × 0.28 × 0.24 mm
β = 79.821 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4048 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3010 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.969	R_int = 0.024
5922 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	9 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.31 e Å⁻³
4048 reflections	Δρ_min = −0.28 e Å⁻³
326 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.1176 (2)	0.5581 (2)	0.34629 (10)	0.0461 (4)
N2	0.2308 (2)	0.30220 (19)	0.36163 (10)	0.0458 (4)
C13	0.2002 (3)	0.4368 (2)	0.39524 (12)	0.0438 (5)
C10	0.2495 (2)	0.4536 (2)	0.47340 (12)	0.0426 (5)
C22	0.1701 (3)	0.2091 (2)	0.23943 (12)	0.0454 (5)
C4	0.4029 (3)	0.6126 (3)	0.74019 (13)	0.0493 (5)
C9	0.1825 (3)	0.5922 (2)	0.51442 (13)	0.0476 (5)
H9	0.1019	0.6761	0.4923	0.057*
C8	0.2336 (3)	0.6071 (2)	0.58706 (13)	0.0499 (5)
H8	0.1882	0.7013	0.6131	0.060*
C14	0.1657 (3)	0.3376 (2)	0.28845 (12)	0.0445 (5)
C7	0.3527 (3)	0.4828 (2)	0.62223 (12)	0.0458 (5)
O2	0.4180 (3)	0.7169 (2)	0.86022 (11)	0.0843 (6)
C12	0.4155 (3)	0.3427 (2)	0.58202 (14)	0.0535 (6)
H12	0.4921	0.2570	0.6055	0.064*
C5	0.3509 (3)	0.7711 (3)	0.70713 (14)	0.0532 (6)
C11	0.3671 (3)	0.3284 (2)	0.50880 (14)	0.0528 (6)
H11	0.4131	0.2345	0.4825	0.063*
C15	0.0948 (3)	0.4979 (2)	0.27737 (12)	0.0448 (5)
C16	0.0128 (3)	0.6002 (2)	0.21090 (13)	0.0473 (5)
C23	0.3001 (3)	0.0680 (2)	0.24136 (13)	0.0533 (6)
H23	0.3865	0.0572	0.2715	0.064*
C26	0.0437 (3)	0.2198 (3)	0.19410 (15)	0.0570 (6)
H26	−0.0445	0.3130	0.1919	0.068*
C17	−0.1236 (3)	0.7339 (2)	0.22837 (14)	0.0524 (6)
H17	−0.1645	0.7595	0.2831	0.063*
N3	0.3101 (3)	0.8982 (3)	0.68135 (14)	0.0735 (6)
C3	0.4488 (3)	0.5846 (3)	0.82517 (16)	0.0648 (7)
C21	0.0700 (3)	0.5658 (3)	0.12820 (14)	0.0595 (6)
H21	0.1614	0.4773	0.1152	0.071*
C20	−0.0064 (4)	0.6604 (3)	0.06561 (15)	0.0697 (7)
H20	0.0333	0.6353	0.0108	0.084*
C27	0.1752 (3)	−0.0438 (3)	0.15516 (15)	0.0655 (7)
H27	0.1765	−0.1288	0.1275	0.079*
C18	−0.1989 (3)	0.8292 (3)	0.16464 (16)	0.0651 (7)
H18	−0.2891	0.9191	0.1768	0.078*
C25	0.0461 (3)	0.0946 (3)	0.15209 (16)	0.0645 (7)
H25	−0.0397	0.1041	0.1218	0.077*
C24	0.3018 (3)	−0.0562 (3)	0.19897 (15)	0.0636 (7)
H24	0.3902	−0.1494	0.2002	0.076*
O1	0.5041 (3)	0.4573 (3)	0.85780 (13)	0.1021 (8)
C19	−0.1412 (4)	0.7919 (3)	0.08367 (17)	0.0717 (7)
H19	−0.1932	0.8554	0.0412	0.086*
O1W	0.0015 (3)	0.8867 (2)	0.38559 (12)	0.0792 (6)
O2W	0.2110 (3)	0.0132 (3)	0.44859 (16)	0.0886 (7)
C1	0.5089 (4)	0.8081 (4)	0.96681 (13)	0.1127 (12)
H1A	0.4386	0.9135	0.9565	0.169*
H1B	0.6168	0.7918	0.9330	0.169*
H1C	0.5229	0.7914	1.0242	0.169*
C2	0.4361 (4)	0.7061 (4)	0.94811 (13)	0.1250 (14)
H2A	0.3257	0.7256	0.9813	0.150*
H2B	0.5032	0.6002	0.9629	0.150*
H2W	0.071 (4)	0.931 (4)	0.396 (2)	0.144 (17)*
H1W	−0.065 (4)	0.952 (4)	0.357 (2)	0.128 (14)*
H3W	0.226 (4)	0.101 (4)	0.423 (2)	0.109 (12)*
H4W	0.168 (5)	0.031 (5)	0.496 (3)	0.145 (18)*
H1	0.088 (3)	0.659 (3)	0.3534 (15)	0.071 (8)*
C6	0.4077 (3)	0.4897 (3)	0.69979 (13)	0.0518 (5)
H6	0.4542	0.3924	0.7262	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0584 (11)	0.0352 (10)	0.0444 (10)	−0.0135 (8)	−0.0060 (8)	−0.0072 (8)
N2	0.0525 (10)	0.0375 (9)	0.0467 (10)	−0.0127 (8)	−0.0049 (8)	−0.0077 (8)
C13	0.0478 (11)	0.0381 (11)	0.0446 (11)	−0.0136 (9)	−0.0025 (9)	−0.0054 (9)
C10	0.0469 (11)	0.0395 (11)	0.0421 (11)	−0.0152 (9)	−0.0030 (9)	−0.0048 (9)
C22	0.0540 (12)	0.0395 (11)	0.0432 (11)	−0.0165 (10)	−0.0012 (9)	−0.0078 (9)
C4	0.0507 (12)	0.0489 (13)	0.0483 (12)	−0.0128 (10)	−0.0135 (10)	−0.0018 (10)
C9	0.0506 (12)	0.0399 (11)	0.0494 (12)	−0.0075 (9)	−0.0115 (9)	−0.0037 (9)
C8	0.0575 (13)	0.0401 (12)	0.0510 (13)	−0.0090 (10)	−0.0125 (10)	−0.0102 (10)
C14	0.0489 (12)	0.0401 (11)	0.0441 (11)	−0.0139 (9)	−0.0024 (9)	−0.0083 (9)
C7	0.0507 (12)	0.0415 (12)	0.0457 (12)	−0.0146 (10)	−0.0088 (9)	−0.0014 (9)
O2	0.1337 (17)	0.0820 (13)	0.0525 (10)	−0.0434 (12)	−0.0331 (11)	−0.0062 (9)
C12	0.0592 (13)	0.0409 (12)	0.0558 (13)	−0.0066 (10)	−0.0149 (11)	−0.0013 (10)
C5	0.0589 (14)	0.0530 (15)	0.0506 (13)	−0.0149 (11)	−0.0151 (11)	−0.0111 (11)
C11	0.0632 (14)	0.0361 (12)	0.0539 (13)	−0.0069 (10)	−0.0080 (11)	−0.0087 (10)
C15	0.0523 (12)	0.0395 (11)	0.0428 (11)	−0.0147 (9)	−0.0041 (9)	−0.0067 (9)
C16	0.0584 (13)	0.0410 (11)	0.0463 (12)	−0.0192 (10)	−0.0085 (10)	−0.0061 (9)
C23	0.0652 (14)	0.0421 (12)	0.0506 (12)	−0.0120 (11)	−0.0081 (10)	−0.0089 (10)
C26	0.0577 (14)	0.0511 (13)	0.0651 (14)	−0.0188 (11)	−0.0074 (11)	−0.0126 (11)
C17	0.0606 (14)	0.0440 (12)	0.0542 (13)	−0.0170 (11)	−0.0082 (10)	−0.0074 (10)
N3	0.0945 (17)	0.0497 (13)	0.0759 (15)	−0.0122 (12)	−0.0292 (12)	−0.0064 (11)
C3	0.0772 (17)	0.0685 (17)	0.0583 (15)	−0.0290 (14)	−0.0267 (13)	0.0015 (13)
C21	0.0755 (16)	0.0504 (13)	0.0501 (13)	−0.0155 (12)	−0.0066 (11)	−0.0094 (11)
C20	0.103 (2)	0.0661 (17)	0.0465 (14)	−0.0301 (16)	−0.0181 (13)	−0.0061 (12)
C27	0.0919 (19)	0.0530 (15)	0.0589 (15)	−0.0327 (14)	−0.0016 (13)	−0.0186 (12)
C18	0.0670 (15)	0.0528 (14)	0.0757 (17)	−0.0120 (12)	−0.0241 (13)	−0.0028 (12)
C25	0.0711 (16)	0.0658 (16)	0.0677 (16)	−0.0316 (14)	−0.0135 (12)	−0.0136 (13)
C24	0.0846 (18)	0.0405 (13)	0.0599 (14)	−0.0108 (12)	−0.0067 (13)	−0.0123 (11)
O1	0.154 (2)	0.0779 (14)	0.0811 (14)	−0.0278 (14)	−0.0646 (14)	0.0158 (11)
C19	0.0910 (19)	0.0665 (17)	0.0666 (17)	−0.0261 (15)	−0.0377 (15)	0.0044 (13)
O1W	0.1181 (17)	0.0475 (11)	0.0756 (13)	−0.0201 (11)	−0.0391 (12)	0.0042 (9)
O2W	0.136 (2)	0.0639 (13)	0.0736 (15)	−0.0457 (13)	−0.0134 (14)	0.0031 (11)
C1	0.161 (3)	0.132 (3)	0.0659 (19)	−0.063 (3)	−0.031 (2)	−0.017 (2)
C2	0.214 (4)	0.151 (3)	0.0583 (18)	−0.111 (3)	−0.053 (2)	0.0087 (19)
C6	0.0549 (13)	0.0468 (12)	0.0518 (13)	−0.0113 (10)	−0.0141 (10)	0.0015 (10)

Geometric parameters (Å, º) top

N1—C13	1.357 (3)	C23—C24	1.379 (3)
N1—C15	1.378 (3)	C23—H23	0.9300
N1—H1	0.88 (3)	C26—C25	1.381 (3)
N2—C13	1.321 (2)	C26—H26	0.9300
N2—C14	1.373 (3)	C17—C18	1.386 (3)
C13—C10	1.456 (3)	C17—H17	0.9300
C10—C9	1.391 (3)	C3—O1	1.195 (3)
C10—C11	1.393 (3)	C21—C20	1.373 (3)
C22—C26	1.385 (3)	C21—H21	0.9300
C22—C23	1.391 (3)	C20—C19	1.374 (4)
C22—C14	1.471 (3)	C20—H20	0.9300
C4—C6	1.342 (3)	C27—C24	1.366 (4)
C4—C5	1.427 (3)	C27—C25	1.373 (4)
C4—C3	1.487 (3)	C27—H27	0.9300
C9—C8	1.373 (3)	C18—C19	1.373 (4)
C9—H9	0.9300	C18—H18	0.9300
C8—C7	1.393 (3)	C25—H25	0.9300
C8—H8	0.9300	C24—H24	0.9300
C14—C15	1.380 (3)	C19—H19	0.9300
C7—C12	1.394 (3)	O1W—H2W	0.86 (4)
C7—C6	1.446 (3)	O1W—H1W	0.834 (18)
O2—C3	1.314 (3)	O2W—H3W	0.89 (4)
O2—C2	1.4674	O2W—H4W	0.81 (4)
C12—C11	1.369 (3)	C1—C2	1.3504
C12—H12	0.9300	C1—H1A	0.9600
C5—N3	1.140 (3)	C1—H1B	0.9600
C11—H11	0.9300	C1—H1C	0.9600
C15—C16	1.468 (3)	C2—H2A	0.9700
C16—C17	1.392 (3)	C2—H2B	0.9700
C16—C21	1.393 (3)	C6—H6	0.9300

C13—N1—C15	108.19 (17)	C25—C26—H26	119.4
C13—N1—H1	128.2 (16)	C22—C26—H26	119.4
C15—N1—H1	123.5 (16)	C18—C17—C16	120.3 (2)
C13—N2—C14	106.65 (16)	C18—C17—H17	119.8
N2—C13—N1	110.47 (18)	C16—C17—H17	119.8
N2—C13—C10	124.99 (18)	O1—C3—O2	124.4 (2)
N1—C13—C10	124.53 (18)	O1—C3—C4	124.1 (2)
C9—C10—C11	118.36 (19)	O2—C3—C4	111.5 (2)
C9—C10—C13	121.92 (18)	C20—C21—C16	121.1 (2)
C11—C10—C13	119.73 (18)	C20—C21—H21	119.5
C26—C22—C23	117.82 (19)	C16—C21—H21	119.5
C26—C22—C14	122.29 (19)	C21—C20—C19	120.3 (2)
C23—C22—C14	119.80 (19)	C21—C20—H20	119.9
C6—C4—C5	123.56 (19)	C19—C20—H20	119.9
C6—C4—C3	118.9 (2)	C24—C27—C25	119.6 (2)
C5—C4—C3	117.5 (2)	C24—C27—H27	120.2
C8—C9—C10	121.08 (19)	C25—C27—H27	120.2
C8—C9—H9	119.5	C19—C18—C17	120.5 (2)
C10—C9—H9	119.5	C19—C18—H18	119.8
C9—C8—C7	120.76 (19)	C17—C18—H18	119.8
C9—C8—H8	119.6	C27—C25—C26	120.0 (2)
C7—C8—H8	119.6	C27—C25—H25	120.0
N2—C14—C15	109.59 (17)	C26—C25—H25	120.0
N2—C14—C22	119.24 (17)	C27—C24—C23	120.8 (2)
C15—C14—C22	131.02 (19)	C27—C24—H24	119.6
C8—C7—C12	117.82 (19)	C23—C24—H24	119.6
C8—C7—C6	123.33 (19)	C18—C19—C20	119.8 (2)
C12—C7—C6	118.79 (19)	C18—C19—H19	120.1
C3—O2—C2	117.12	C20—C19—H19	120.1
C11—C12—C7	121.5 (2)	H2W—O1W—H1W	107 (2)
C11—C12—H12	119.2	H3W—O2W—H4W	109 (4)
C7—C12—H12	119.2	C2—C1—H1A	109.5
N3—C5—C4	179.3 (2)	C2—C1—H1B	109.5
C12—C11—C10	120.42 (19)	H1A—C1—H1B	109.5
C12—C11—H11	119.8	C2—C1—H1C	109.5
C10—C11—H11	119.8	H1A—C1—H1C	109.5
N1—C15—C14	105.09 (18)	H1B—C1—H1C	109.5
N1—C15—C16	121.59 (18)	C1—C2—O2	113.40
C14—C15—C16	133.31 (19)	C1—C2—H2A	108.9
C17—C16—C21	118.1 (2)	O2—C2—H2A	108.9
C17—C16—C15	121.25 (19)	C1—C2—H2B	108.9
C21—C16—C15	120.7 (2)	O2—C2—H2B	108.9
C24—C23—C22	120.5 (2)	H2A—C2—H2B	107.7
C24—C23—H23	119.7	C4—C6—C7	131.0 (2)
C22—C23—H23	119.7	C4—C6—H6	114.5
C25—C26—C22	121.2 (2)	C7—C6—H6	114.5

C14—N2—C13—N1	0.0 (2)	N1—C15—C16—C17	−38.2 (3)
C14—N2—C13—C10	−179.44 (19)	C14—C15—C16—C17	143.4 (2)
C15—N1—C13—N2	−0.3 (2)	N1—C15—C16—C21	141.8 (2)
C15—N1—C13—C10	179.10 (18)	C14—C15—C16—C21	−36.7 (4)
N2—C13—C10—C9	−165.5 (2)	C26—C22—C23—C24	0.3 (3)
N1—C13—C10—C9	15.2 (3)	C14—C22—C23—C24	176.9 (2)
N2—C13—C10—C11	14.7 (3)	C23—C22—C26—C25	0.0 (3)
N1—C13—C10—C11	−164.7 (2)	C14—C22—C26—C25	−176.5 (2)
C11—C10—C9—C8	1.5 (3)	C21—C16—C17—C18	−0.1 (3)
C13—C10—C9—C8	−178.4 (2)	C15—C16—C17—C18	179.8 (2)
C10—C9—C8—C7	−0.8 (3)	C2—O2—C3—O1	−6.81
C13—N2—C14—C15	0.4 (2)	C2—O2—C3—C4	171.99
C13—N2—C14—C22	−175.68 (18)	C6—C4—C3—O1	6.8 (4)
C26—C22—C14—N2	145.5 (2)	C5—C4—C3—O1	−175.1 (3)
C23—C22—C14—N2	−30.9 (3)	C6—C4—C3—O2	−172.1 (2)
C26—C22—C14—C15	−29.5 (3)	C5—C4—C3—O2	6.0 (3)
C23—C22—C14—C15	154.0 (2)	C17—C16—C21—C20	−0.4 (4)
C9—C8—C7—C12	−1.1 (3)	C15—C16—C21—C20	179.7 (2)
C9—C8—C7—C6	−178.1 (2)	C16—C21—C20—C19	0.2 (4)
C8—C7—C12—C11	2.3 (3)	C16—C17—C18—C19	0.8 (4)
C6—C7—C12—C11	179.4 (2)	C24—C27—C25—C26	−0.8 (4)
C6—C4—C5—N3	−166 (25)	C22—C26—C25—C27	0.3 (4)
C3—C4—C5—N3	16 (25)	C25—C27—C24—C23	1.1 (4)
C7—C12—C11—C10	−1.6 (3)	C22—C23—C24—C27	−0.8 (4)
C9—C10—C11—C12	−0.3 (3)	C17—C18—C19—C20	−0.9 (4)
C13—C10—C11—C12	179.6 (2)	C21—C20—C19—C18	0.4 (4)
C13—N1—C15—C14	0.5 (2)	C3—O2—C2—C1	139.63
C13—N1—C15—C16	−178.30 (18)	C5—C4—C6—C7	−5.9 (4)
N2—C14—C15—N1	−0.5 (2)	C3—C4—C6—C7	172.0 (2)
C22—C14—C15—N1	174.9 (2)	C8—C7—C6—C4	−21.8 (4)
N2—C14—C15—C16	178.1 (2)	C12—C7—C6—C4	161.2 (2)
C22—C14—C15—C16	−6.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.88 (3)	2.04 (3)	2.915 (3)	172 (2)
O2W—H3W···N2	0.89 (4)	1.98 (4)	2.870 (3)	173 (3)
C9—H9···O1W	0.93	2.48	3.338 (3)	154
C6—H6···O1	0.93	2.44	2.813 (3)	104
C2—H2B···O1	0.97	2.27	2.680 (3)	105
O1W—H2W···O2Wⁱ	0.86 (4)	1.95 (2)	2.789 (3)	165 (4)
O1W—H1W···N3ⁱⁱ	0.83 (2)	2.24 (2)	3.034 (3)	159 (3)
O2W—H4W···O1Wⁱⁱⁱ	0.81 (4)	2.25 (4)	3.041 (4)	167 (4)

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₇H₂₁N₃O₂·2H₂O
M_r	455.50
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.4976 (16), 9.0263 (17), 16.421 (3)
α, β, γ (°)	83.536 (2), 79.821 (2), 71.089 (2)
V (Å³)	1170.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.28 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.962, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	5922, 4048, 3010
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.134, 1.03
No. of reflections	4048
No. of parameters	326
No. of restraints	9
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.28

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.88 (3)	2.04 (3)	2.915 (3)	172 (2)
O2W—H3W···N2	0.89 (4)	1.98 (4)	2.870 (3)	173 (3)
C9—H9···O1W	0.93	2.48	3.338 (3)	154
C6—H6···O1	0.93	2.44	2.813 (3)	104
C2—H2B···O1	0.97	2.27	2.680 (3)	105
O1W—H2W···O2Wⁱ	0.86 (4)	1.95 (2)	2.789 (3)	165 (4)
O1W—H1W···N3ⁱⁱ	0.83 (2)	2.24 (2)	3.034 (3)	159 (3)
O2W—H4W···O1Wⁱⁱⁱ	0.81 (4)	2.25 (4)	3.041 (4)	167 (4)

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+2, −z+1; (iii) −x, −y+1, −z+1.

Acknowledgements

We are grateful to the Doctoral Program Foundation of the Natural Science Foundation of Guangdong Province, China (No. 5100430) for financial support.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fridman, N., Kaftory, M., Eichen, Y. & Speiser, S. (2009). J. Mol. Struct. 917, 101–109. CrossRef CAS Google Scholar
Liu, X. F., Zhong, Z. P. & Xu, Z. L. (2006). Fen Xi Ce Shi Xue Bao, 25, 6–10. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Valiyev, F., Hu, W. S., Chen, H. Y., Kuo, M. Y., Chao, I. & Tao, Y. T. (2007). Chem. Mater. 19, 3018–3026. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 3| March 2011| Page o707

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-Ethyl 2-cyano-3-[4-(4,5-di­phenyl-1H-imidazol-2-yl)phen­yl]acrylate dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

(E)-Ethyl 2-cyano-3-[4-(4,5-diphenyl-1H-imidazol-2-yl)phenyl]acrylate dihydrate