(Z)-4-(2-Hy­droxy­benzyl­idene)-1-methyl-2-phenyl-1H-imidazol-5(4H)-one

Chang, M.-J.; Tsai, H.-Y.; Fang, T.-C.; Luo, M.-H.; Chen, K.-Y.

doi:10.1107/S1600536812007921

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o902-o903

doi:10.1107/S1600536812007921

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(Z)-4-(2-Hydroxybenzylidene)-1-methyl-2-phenyl-1H-imidazol-5(4H)-one

Ming-Jen Chang,^a Hsing-Yang Tsai,^a Tzu-Chien Fang,^a Ming-Hui Luo ^a and Kew-Yu Chen ^a ^*

^aDepartment of Chemical Engineering, Feng Chia University, 40724 Taichung, Taiwan
^*Correspondence e-mail: kyuchen@fcu.edu.tw

(Received 10 February 2012; accepted 22 February 2012; online 29 February 2012)

In the title compound, C₁₇H₁₄N₂O₂, the asymmetric unit comprises two molecules that are comformationally similar [the dihedral angles between the phenyl rings in each are 46.35 (2) and 48.04 (3)°], with the conformation stabilized by intramolecular O—H⋯N hydrogen bonds, which generate S(7) rings. In the crystal, inversion-related molecules are linked by pairs of weak C—H⋯O hydrogen bonds, forming dimers with an R₂²(16) graph-set motif. Weak inter-ring π–π stacking is observed in the structure, the shortest centroid-to-centroid distance being 3.7480 (13) Å.

Related literature

For the spectroscopy and preparation of the title compound, see: Chuang et al. (2011 ). For the applications of proton-transfer dyes, see: Chen & Pang (2010 ); Gryko et al. (2010 ); Han et al. (2010 ); Helal et al. (2010 ); Ikeda et al. (2010 ); Ito et al. (2011 ); Lim et al. (2011 ); Lins et al. (2010 ); Maupin et al. (2011 ); Santos et al. (2011 ); Tang et al. (2011 ). For a related structure, see: Chen et al. (2007 ). For graph-set theory of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₄N₂O₂
M_r = 278.30
Triclinic, $[P \overline 1]$
a = 9.7843 (4) Å
b = 9.8972 (3) Å
c = 15.4313 (6) Å
α = 72.086 (2)°
β = 79.301 (2)°
γ = 70.500 (2)°
V = 1334.57 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.32 × 0.28 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.889, T_max = 0.984
20392 measured reflections
4699 independent reflections
2273 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.101
S = 0.80
4699 reflections
382 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.80	2.615 (2)	176
O4—H4⋯N4	0.82	1.79	2.612 (3)	175
C10—H10⋯O1ⁱ	0.93	2.58	3.403 (3)	148
C30—H30⋯O3ⁱⁱ	0.93	2.68	3.421 (3)	137
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007921/zs2183sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007921/zs2183Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007921/zs2183Isup3.cml

checkCIF report

Comment top

The excited-state intramolecular proton transfer (ESIPT) reaction of the title compound has been investigated recently (Chuang et al., 2011), which involves transfer of a hydroxy proton to the imine nitrogen through an intramolecular seven-membered ring hydrogen-bonding system. The proton-transfer dyes have found many important applications. Prototypical examples are probes for solvation dynamics (Chen & Pang, 2010; Lins et al.) and biological environments (Lim et al., 2011; Maupin et al., 2011), near-infrared fluorescent dyes (Ikeda et al., 2010), chemosensors (Han et al., 2010; Helal et al., 2010), photochromic materials (Ito et al., 2011), fluorescence microscopy imaging (Santos et al., 2011), and recent applications in the field of organic light-emitting devices (Gryko et al., 2010; Tang et al., 2011).

The molecular structure of the title compound, C₁₇H₁₄N₂O₂ is shown in Fig. 1. The asymmetric unit comprises two symmetry-independent molecules (A and B) which are comformationally similar [dihedral angles between the phenyl rings in each are 46.35 (2) and 48.04 (3)°]. The conformation stabilized in each by intramolecular O—H···N hydrogen bonds which generate S(7) rings (Chen et al., 2007). Present also are intramolecular C—H···O interactions between the methyl group and the ketone O-atom, generating S(5) rings (Table 1). In the crystal (Fig. 2), inversion-related molecules are linked by pairs of weak hydrogen bonds (Table 1), forming cyclic dimers with an R₂²(16) graph-set motif (Bernstein et al., 1995). Weak π–π stacking is also observed in the crystal structure, the shortest centroid–centroid distance being 3.7480 (13) Å [symmetry code: x, y - 1, z].

Related literature top

For the spectroscopy and preparation of the title compound, see: Chuang et al. (2011). For the applications of proton-transfer dyes, see: Chen & Pang (2010); Gryko et al. (2010); Han et al. (2010); Helal et al. (2010); Ikeda et al. (2010); Ito et al. (2011); Lim et al. (2011); Lins et al. (2010); Maupin et al. (2011); Santos et al. (2011); Tang et al. (2011). For a related structure, see: Chen et al. (2007). For graph-set theory of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized according to the literature procedure (Chuang et al., 2011). Yellow needle-shaped crystals suitable for the crystallographic studies reported here were isolated over a period of six weeks by slow evaporation from a chloroform solution.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. A section of the crystal packing of the title compound, viewed along the b axis. Green and blue dashed lines denote the intermolecular C10—H10···O1ⁱ and C30—H30···O3ⁱⁱ hydrogen bonds, respectively. For symmetry codes (i) and (ii), see Table 1.

(Z)-4-(2-Hydroxybenzylidene)-1-methyl-2-phenyl-1H- imidazol-5(4H)-one top

Crystal data top

C₁₇H₁₄N₂O₂	Z = 4
M_r = 278.30	F(000) = 584
Triclinic, P1	D_x = 1.385 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7843 (4) Å	Cell parameters from 3314 reflections
b = 9.8972 (3) Å	θ = 2.5–25.0°
c = 15.4313 (6) Å	µ = 0.09 mm⁻¹
α = 72.086 (2)°	T = 150 K
β = 79.301 (2)°	Prism, yellow
γ = 70.500 (2)°	0.32 × 0.28 × 0.14 mm
V = 1334.57 (9) Å³

Data collection top

Bruker SMART CCD diffractometer	4699 independent reflections
Radiation source: fine-focus sealed tube	2273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.889, T_max = 0.984	k = −11→10
20392 measured reflections	l = −18→18

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.049P)²] where P = (F_o² + 2F_c²)/3
S = 0.80	(Δ/σ)_max < 0.001
4699 reflections	Δρ_max = 0.35 e Å⁻³
382 parameters	Δρ_min = −0.36 e Å⁻³
0 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: 0.037 (2)

Crystal data top

C₁₇H₁₄N₂O₂	γ = 70.500 (2)°
M_r = 278.30	V = 1334.57 (9) Å³
Triclinic, P1	Z = 4
a = 9.7843 (4) Å	Mo Kα radiation
b = 9.8972 (3) Å	µ = 0.09 mm⁻¹
c = 15.4313 (6) Å	T = 150 K
α = 72.086 (2)°	0.32 × 0.28 × 0.14 mm
β = 79.301 (2)°

Data collection top

Bruker SMART CCD diffractometer	4699 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2273 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.984	R_int = 0.054
20392 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 0.80	Δρ_max = 0.35 e Å⁻³
4699 reflections	Δρ_min = −0.36 e Å⁻³
382 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
O1	0.13687 (16)	−0.12970 (16)	0.02374 (11)	0.0292 (4)
O2	0.24941 (16)	0.01412 (16)	0.32193 (9)	0.0331 (5)
H2	0.1962	−0.0125	0.2996	0.050*
O3	0.15388 (16)	0.37862 (16)	0.01672 (11)	0.0299 (4)
O4	0.23819 (17)	0.52664 (17)	0.32188 (10)	0.0410 (5)
H4	0.1961	0.4877	0.2999	0.061*
N1	−0.00550 (19)	−0.16641 (18)	0.16225 (12)	0.0229 (5)
N2	0.09021 (19)	−0.07230 (18)	0.24367 (12)	0.0219 (5)
N3	0.00423 (19)	0.34215 (18)	0.15218 (12)	0.0228 (5)
N4	0.10847 (19)	0.41218 (18)	0.24187 (12)	0.0227 (5)
C1	−0.0086 (2)	−0.1355 (2)	0.24468 (15)	0.0223 (6)
C2	0.1046 (2)	−0.1190 (2)	0.10228 (16)	0.0227 (6)
C3	0.1655 (2)	−0.0577 (2)	0.15660 (15)	0.0206 (6)
C4	−0.1125 (2)	−0.2116 (2)	0.13239 (15)	0.0306 (6)
H4A	−0.1132	−0.1750	0.0671	0.046*
H4B	−0.2073	−0.1713	0.1609	0.046*
H4C	−0.0875	−0.3181	0.1495	0.046*
C5	0.2778 (2)	−0.0006 (2)	0.12414 (15)	0.0215 (6)
H5	0.3074	0.0033	0.0628	0.026*
C6	0.3625 (2)	0.0560 (2)	0.16442 (15)	0.0193 (6)
C7	0.3494 (2)	0.0583 (2)	0.25650 (16)	0.0232 (6)
C8	0.4470 (3)	0.1070 (2)	0.28520 (16)	0.0307 (7)
H8	0.4385	0.1081	0.3460	0.037*
C9	0.5556 (3)	0.1535 (2)	0.22577 (16)	0.0312 (7)
H9	0.6200	0.1846	0.2469	0.037*
C10	0.5697 (2)	0.1544 (2)	0.13480 (16)	0.0288 (6)
H10	0.6424	0.1868	0.0941	0.035*
C11	0.4740 (2)	0.1065 (2)	0.10597 (15)	0.0251 (6)
H11	0.4834	0.1074	0.0447	0.030*
C13	−0.1095 (2)	−0.1721 (2)	0.32475 (15)	0.0213 (6)
C14	−0.1679 (2)	−0.0741 (2)	0.37879 (15)	0.0259 (6)
H14	−0.1459	0.0154	0.3627	0.031*
C15	−0.2590 (2)	−0.1091 (2)	0.45685 (16)	0.0316 (7)
H15	−0.2995	−0.0424	0.4925	0.038*
C16	−0.2899 (3)	−0.2423 (3)	0.48168 (16)	0.0335 (7)
H16	−0.3511	−0.2654	0.5342	0.040*
C17	−0.2304 (3)	−0.3420 (3)	0.42909 (17)	0.0403 (7)
H17	−0.2504	−0.4327	0.4465	0.048*
C18	−0.1414 (3)	−0.3063 (2)	0.35063 (16)	0.0342 (7)
H18	−0.1023	−0.3729	0.3147	0.041*
C21	0.0052 (2)	0.3587 (2)	0.23784 (15)	0.0213 (6)
C22	0.1193 (2)	0.3853 (2)	0.09563 (16)	0.0224 (6)
C23	0.1837 (2)	0.4354 (2)	0.15464 (15)	0.0218 (6)
C24	−0.0927 (2)	0.2851 (2)	0.12174 (15)	0.0300 (6)
H24A	−0.0467	0.2512	0.0685	0.045*
H24B	−0.1819	0.3626	0.1071	0.045*
H24C	−0.1133	0.2037	0.1696	0.045*
C25	0.2933 (2)	0.4973 (2)	0.12575 (15)	0.0241 (6)
H25	0.3284	0.5009	0.0650	0.029*
C26	0.3682 (2)	0.5595 (2)	0.16923 (16)	0.0219 (6)
C27	0.3378 (2)	0.5747 (2)	0.25873 (16)	0.0238 (6)
C28	0.4158 (3)	0.6439 (2)	0.28910 (16)	0.0288 (6)
H28	0.3938	0.6553	0.3482	0.035*
C29	0.5248 (3)	0.6955 (2)	0.23309 (17)	0.0314 (7)
H29	0.5759	0.7410	0.2544	0.038*
C30	0.5579 (2)	0.6795 (2)	0.14511 (17)	0.0319 (7)
H30	0.6319	0.7136	0.1071	0.038*
C31	0.4811 (2)	0.6132 (2)	0.11422 (16)	0.0289 (6)
H31	0.5042	0.6032	0.0548	0.035*
C33	−0.0964 (2)	0.3198 (2)	0.31732 (15)	0.0221 (6)
C34	−0.0444 (3)	0.2553 (2)	0.40301 (16)	0.0295 (6)
H34	0.0537	0.2357	0.4088	0.035*
C35	−0.1373 (3)	0.2200 (2)	0.47980 (16)	0.0334 (7)
H35	−0.1012	0.1757	0.5368	0.040*
C36	−0.2833 (3)	0.2502 (2)	0.47222 (16)	0.0290 (6)
H36	−0.3458	0.2261	0.5239	0.035*
C37	−0.3360 (3)	0.3161 (2)	0.38798 (16)	0.0282 (6)
H37	−0.4348	0.3376	0.3830	0.034*
C38	−0.2438 (2)	0.3510 (2)	0.31025 (15)	0.0254 (6)
H38	−0.2807	0.3952	0.2535	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0265 (10)	0.0404 (10)	0.0249 (11)	−0.0125 (8)	0.0015 (8)	−0.0138 (9)
O2	0.0353 (11)	0.0523 (11)	0.0223 (10)	−0.0289 (9)	0.0055 (9)	−0.0123 (8)
O3	0.0312 (11)	0.0353 (10)	0.0240 (11)	−0.0109 (9)	0.0004 (9)	−0.0096 (9)
O4	0.0483 (12)	0.0557 (12)	0.0318 (11)	−0.0307 (10)	0.0043 (10)	−0.0175 (9)
N1	0.0195 (12)	0.0289 (12)	0.0253 (13)	−0.0123 (10)	0.0000 (10)	−0.0099 (10)
N2	0.0184 (12)	0.0245 (11)	0.0230 (13)	−0.0092 (10)	0.0017 (10)	−0.0055 (9)
N3	0.0228 (13)	0.0275 (12)	0.0217 (12)	−0.0112 (10)	−0.0014 (10)	−0.0079 (10)
N4	0.0206 (12)	0.0259 (11)	0.0228 (13)	−0.0098 (10)	0.0011 (10)	−0.0068 (9)
C1	0.0199 (15)	0.0205 (14)	0.0256 (16)	−0.0033 (12)	−0.0017 (12)	−0.0078 (12)
C2	0.0187 (15)	0.0232 (14)	0.0241 (16)	−0.0041 (12)	−0.0015 (13)	−0.0061 (12)
C3	0.0170 (14)	0.0212 (13)	0.0217 (15)	−0.0042 (11)	−0.0019 (12)	−0.0044 (11)
C4	0.0265 (16)	0.0392 (16)	0.0340 (17)	−0.0156 (13)	−0.0043 (13)	−0.0136 (13)
C5	0.0208 (15)	0.0233 (14)	0.0171 (14)	−0.0032 (12)	−0.0008 (11)	−0.0049 (11)
C6	0.0164 (14)	0.0186 (13)	0.0208 (15)	−0.0044 (11)	−0.0010 (12)	−0.0036 (11)
C7	0.0217 (15)	0.0229 (14)	0.0244 (16)	−0.0086 (12)	0.0017 (12)	−0.0054 (12)
C8	0.0332 (16)	0.0412 (16)	0.0242 (16)	−0.0164 (14)	−0.0004 (13)	−0.0133 (13)
C9	0.0283 (16)	0.0406 (16)	0.0325 (17)	−0.0189 (13)	−0.0029 (13)	−0.0113 (13)
C10	0.0197 (15)	0.0357 (15)	0.0334 (17)	−0.0145 (13)	0.0025 (13)	−0.0084 (13)
C11	0.0227 (15)	0.0282 (14)	0.0239 (15)	−0.0070 (12)	0.0010 (12)	−0.0084 (12)
C13	0.0176 (14)	0.0243 (14)	0.0231 (15)	−0.0084 (12)	−0.0009 (12)	−0.0058 (12)
C14	0.0264 (15)	0.0258 (14)	0.0269 (15)	−0.0106 (12)	−0.0003 (12)	−0.0068 (12)
C15	0.0316 (16)	0.0329 (16)	0.0312 (17)	−0.0101 (13)	0.0045 (13)	−0.0135 (13)
C16	0.0296 (17)	0.0405 (16)	0.0319 (17)	−0.0190 (14)	0.0078 (13)	−0.0086 (14)
C17	0.0440 (18)	0.0402 (17)	0.0427 (18)	−0.0269 (15)	0.0126 (15)	−0.0134 (14)
C18	0.0376 (17)	0.0318 (16)	0.0386 (17)	−0.0162 (13)	0.0071 (14)	−0.0166 (13)
C21	0.0220 (15)	0.0184 (14)	0.0222 (16)	−0.0052 (12)	−0.0017 (12)	−0.0048 (12)
C22	0.0222 (15)	0.0193 (14)	0.0215 (16)	−0.0027 (11)	−0.0011 (13)	−0.0038 (12)
C23	0.0192 (14)	0.0233 (14)	0.0210 (15)	−0.0058 (12)	0.0015 (12)	−0.0057 (12)
C24	0.0318 (16)	0.0322 (15)	0.0303 (16)	−0.0111 (13)	−0.0054 (13)	−0.0109 (12)
C25	0.0229 (15)	0.0230 (14)	0.0227 (15)	−0.0039 (12)	0.0026 (12)	−0.0068 (12)
C26	0.0202 (15)	0.0194 (14)	0.0256 (16)	−0.0047 (12)	−0.0013 (12)	−0.0073 (12)
C27	0.0217 (15)	0.0236 (14)	0.0243 (16)	−0.0090 (12)	0.0012 (12)	−0.0032 (12)
C28	0.0324 (16)	0.0286 (14)	0.0257 (16)	−0.0059 (13)	−0.0073 (13)	−0.0081 (12)
C29	0.0250 (16)	0.0274 (15)	0.0443 (19)	−0.0077 (13)	−0.0107 (14)	−0.0087 (14)
C30	0.0205 (15)	0.0297 (15)	0.0430 (19)	−0.0080 (12)	0.0009 (13)	−0.0080 (14)
C31	0.0249 (16)	0.0252 (14)	0.0363 (17)	−0.0089 (12)	−0.0019 (13)	−0.0066 (13)
C33	0.0229 (15)	0.0215 (14)	0.0234 (16)	−0.0087 (12)	−0.0009 (12)	−0.0068 (12)
C34	0.0245 (15)	0.0384 (16)	0.0283 (16)	−0.0130 (13)	−0.0031 (13)	−0.0080 (13)
C35	0.0361 (17)	0.0436 (17)	0.0226 (16)	−0.0178 (14)	−0.0025 (13)	−0.0050 (13)
C36	0.0299 (17)	0.0327 (15)	0.0253 (16)	−0.0139 (13)	0.0061 (13)	−0.0091 (13)
C37	0.0207 (15)	0.0283 (15)	0.0354 (17)	−0.0094 (12)	0.0015 (13)	−0.0079 (13)
C38	0.0248 (15)	0.0257 (14)	0.0248 (15)	−0.0080 (12)	−0.0035 (12)	−0.0043 (12)

Geometric parameters (Å, º) top

O1—C2	1.222 (2)	C14—H14	0.9300
O2—C7	1.347 (2)	C15—C16	1.373 (3)
O2—H2	0.8200	C15—H15	0.9300
O3—C22	1.218 (2)	C16—C17	1.380 (3)
O4—C27	1.341 (2)	C16—H16	0.9300
O4—H4	0.8200	C17—C18	1.378 (3)
N1—C2	1.392 (3)	C17—H17	0.9300
N1—C1	1.390 (3)	C18—H18	0.9300
N1—C4	1.458 (2)	C21—C33	1.467 (3)
N2—C1	1.311 (2)	C22—C23	1.474 (3)
N2—C3	1.397 (3)	C23—C25	1.348 (3)
N3—C21	1.383 (3)	C24—H24A	0.9600
N3—C22	1.392 (3)	C24—H24B	0.9600
N3—C24	1.458 (2)	C24—H24C	0.9600
N4—C21	1.306 (2)	C25—C26	1.450 (3)
N4—C23	1.400 (3)	C25—H25	0.9300
C1—C13	1.464 (3)	C26—C27	1.402 (3)
C2—C3	1.471 (3)	C26—C31	1.410 (3)
C3—C5	1.347 (3)	C27—C28	1.396 (3)
C4—H4A	0.9600	C28—C29	1.376 (3)
C4—H4B	0.9600	C28—H28	0.9300
C4—H4C	0.9600	C29—C30	1.381 (3)
C5—C6	1.449 (3)	C29—H29	0.9300
C5—H5	0.9300	C30—C31	1.371 (3)
C6—C11	1.406 (3)	C30—H30	0.9300
C6—C7	1.409 (3)	C31—H31	0.9300
C7—C8	1.392 (3)	C33—C34	1.388 (3)
C8—C9	1.374 (3)	C33—C38	1.389 (3)
C8—H8	0.9300	C34—C35	1.382 (3)
C9—C10	1.382 (3)	C34—H34	0.9300
C9—H9	0.9300	C35—C36	1.378 (3)
C10—C11	1.372 (3)	C35—H35	0.9300
C10—H10	0.9300	C36—C37	1.373 (3)
C11—H11	0.9300	C36—H36	0.9300
C13—C14	1.383 (3)	C37—C38	1.387 (3)
C13—C18	1.388 (3)	C37—H37	0.9300
C14—C15	1.385 (3)	C38—H38	0.9300

C7—O2—H2	109.5	C18—C17—H17	120.2
C27—O4—H4	109.5	C16—C17—H17	120.2
C2—N1—C1	108.23 (18)	C17—C18—C13	120.6 (2)
C2—N1—C4	122.40 (19)	C17—C18—H18	119.7
C1—N1—C4	128.31 (19)	C13—C18—H18	119.7
C1—N2—C3	106.55 (18)	N4—C21—N3	112.87 (19)
C21—N3—C22	108.32 (18)	N4—C21—C33	122.4 (2)
C21—N3—C24	128.78 (18)	N3—C21—C33	124.7 (2)
C22—N3—C24	122.86 (19)	O3—C22—N3	125.6 (2)
C21—N4—C23	106.86 (19)	O3—C22—C23	130.9 (2)
N2—C1—N1	112.80 (19)	N3—C22—C23	103.46 (19)
N2—C1—C13	123.5 (2)	C25—C23—N4	127.5 (2)
N1—C1—C13	123.68 (19)	C25—C23—C22	124.1 (2)
O1—C2—N1	125.2 (2)	N4—C23—C22	108.41 (18)
O1—C2—C3	131.3 (2)	N3—C24—H24A	109.5
N1—C2—C3	103.43 (19)	N3—C24—H24B	109.5
C5—C3—N2	128.0 (2)	H24A—C24—H24B	109.5
C5—C3—C2	123.0 (2)	N3—C24—H24C	109.5
N2—C3—C2	108.99 (18)	H24A—C24—H24C	109.5
N1—C4—H4A	109.5	H24B—C24—H24C	109.5
N1—C4—H4B	109.5	C23—C25—C26	133.6 (2)
H4A—C4—H4B	109.5	C23—C25—H25	113.2
N1—C4—H4C	109.5	C26—C25—H25	113.2
H4A—C4—H4C	109.5	C27—C26—C31	117.1 (2)
H4B—C4—H4C	109.5	C27—C26—C25	126.9 (2)
C3—C5—C6	133.7 (2)	C31—C26—C25	115.9 (2)
C3—C5—H5	113.2	O4—C27—C28	114.2 (2)
C6—C5—H5	113.2	O4—C27—C26	125.9 (2)
C11—C6—C7	117.1 (2)	C28—C27—C26	120.0 (2)
C11—C6—C5	116.0 (2)	C29—C28—C27	121.1 (2)
C7—C6—C5	126.9 (2)	C29—C28—H28	119.4
O2—C7—C8	115.5 (2)	C27—C28—H28	119.4
O2—C7—C6	125.2 (2)	C28—C29—C30	119.8 (2)
C8—C7—C6	119.3 (2)	C28—C29—H29	120.1
C9—C8—C7	121.5 (2)	C30—C29—H29	120.1
C9—C8—H8	119.2	C31—C30—C29	119.5 (2)
C7—C8—H8	119.2	C31—C30—H30	120.2
C8—C9—C10	120.4 (2)	C29—C30—H30	120.2
C8—C9—H9	119.8	C30—C31—C26	122.4 (2)
C10—C9—H9	119.8	C30—C31—H31	118.8
C11—C10—C9	118.4 (2)	C26—C31—H31	118.8
C11—C10—H10	120.8	C34—C33—C38	118.9 (2)
C9—C10—H10	120.8	C34—C33—C21	118.9 (2)
C10—C11—C6	123.3 (2)	C38—C33—C21	122.2 (2)
C10—C11—H11	118.4	C35—C34—C33	120.6 (2)
C6—C11—H11	118.4	C35—C34—H34	119.7
C14—C13—C18	119.2 (2)	C33—C34—H34	119.7
C14—C13—C1	119.10 (19)	C36—C35—C34	120.2 (2)
C18—C13—C1	121.6 (2)	C36—C35—H35	119.9
C13—C14—C15	120.1 (2)	C34—C35—H35	119.9
C13—C14—H14	119.9	C37—C36—C35	119.6 (2)
C15—C14—H14	119.9	C37—C36—H36	120.2
C16—C15—C14	120.1 (2)	C35—C36—H36	120.2
C16—C15—H15	119.9	C36—C37—C38	120.8 (2)
C14—C15—H15	119.9	C36—C37—H37	119.6
C15—C16—C17	120.3 (2)	C38—C37—H37	119.6
C15—C16—H16	119.8	C33—C38—C37	119.9 (2)
C17—C16—H16	119.8	C33—C38—H38	120.1
C18—C17—C16	119.6 (2)	C37—C38—H38	120.1

C2—N1—C1—N2	−0.1 (2)	C3—C5—C6—C7	3.3 (4)
C2—N1—C1—C13	−179.03 (19)	C3—C5—C6—C11	179.8 (2)
C4—N1—C1—N2	−168.39 (19)	C5—C6—C7—O2	−3.5 (3)
C1—N1—C2—O1	179.9 (2)	C5—C6—C7—C8	175.3 (2)
C1—N1—C2—C3	0.0 (2)	C11—C6—C7—O2	−179.95 (18)
C4—N1—C2—O1	−11.0 (3)	C11—C6—C7—C8	−1.1 (3)
C4—N1—C2—C3	169.06 (17)	C5—C6—C11—C10	−175.71 (19)
C3—N2—C1—N1	0.3 (2)	C7—C6—C11—C10	1.1 (3)
C3—N2—C1—C13	179.15 (19)	O2—C7—C8—C9	179.22 (19)
C1—N2—C3—C2	−0.3 (2)	C6—C7—C8—C9	0.3 (3)
C1—N2—C3—C5	−179.1 (2)	C7—C8—C9—C10	0.7 (3)
N1—C1—C13—C14	−142.3 (2)	C8—C9—C10—C11	−0.7 (3)
N1—C1—C13—C18	41.4 (3)	C9—C10—C11—C6	−0.2 (3)
N2—C1—C13—C14	38.9 (3)	C1—C13—C14—C15	−177.4 (2)
N2—C1—C13—C18	−137.4 (2)	C18—C13—C14—C15	−1.1 (3)
O1—C2—C3—N2	−179.8 (2)	C1—C13—C18—C17	176.4 (2)
O1—C2—C3—C5	−0.8 (4)	C14—C13—C18—C17	0.1 (4)
N1—C2—C3—N2	0.2 (2)	C13—C14—C15—C16	1.0 (3)
N1—C2—C3—C5	179.09 (19)	C14—C15—C16—C17	0.0 (4)
N2—C3—C5—C6	3.6 (4)	C15—C16—C17—C18	−1.0 (4)
C2—C3—C5—C6	−175.1 (2)	C16—C17—C18—C13	0.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.80	2.615 (2)	176
O4—H4···N4	0.82	1.79	2.612 (3)	175
C4—H4A···O1	0.96	2.56	2.896 (3)	100
C10—H10···O1ⁱ	0.93	2.58	3.403 (3)	148
C30—H30···O3ⁱⁱ	0.93	2.68	3.421 (3)	137
C24—H24A···O3	0.96	2.56	2.902 (3)	101

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄N₂O₂
M_r	278.30
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	9.7843 (4), 9.8972 (3), 15.4313 (6)
α, β, γ (°)	72.086 (2), 79.301 (2), 70.500 (2)
V (Å³)	1334.57 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.28 × 0.14

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.889, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	20392, 4699, 2273
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.101, 0.80
No. of reflections	4699
No. of parameters	382
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.36

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.80	2.615 (2)	176
O4—H4···N4	0.82	1.79	2.612 (3)	175
C10—H10···O1ⁱ	0.93	2.58	3.403 (3)	148
C30—H30···O3ⁱⁱ	0.93	2.68	3.421 (3)	137

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

Acknowledgements

This work was supported by the National Science Council (grant No. NSC 99-2113-M-035-001-MY2) and Feng Chia University, Taiwan.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, K.-Y., Cheng, Y.-M., Lai, C.-H., Hsu, C.-C., Ho, M.-L., Lee, G.-H. & Chou, P.-T. (2007). J. Am. Chem. Soc. 129, 4534–4535. Web of Science CSD CrossRef PubMed CAS Google Scholar
Chen, W.-H. & Pang, Y. (2010). Tetrahedron Lett. 51, 1914–1918. Web of Science CrossRef CAS Google Scholar
Chuang, W.-T., Hsieh, C.-C., Lai, C.-H., Lai, C.-H., Shih, C.-W., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Org. Chem. 76, 8189–8202. Web of Science CSD CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gryko, D. T., Piechowska, J. & Galezowski, M. (2010). J. Org. Chem. 75, 1297–1300. Web of Science CrossRef CAS PubMed Google Scholar
Han, D. Y., Kim, J. M., Kim, J., Jung, H. S., Lee, Y. H., Zhang, J. F. & Kim, J. S. (2010). Tetrahedron Lett. 51, 1947–1951. Web of Science CSD CrossRef CAS Google Scholar
Helal, A., Lee, S. H., Kim, S. H. & Kim, H.-S. (2010). Tetrahedron Lett. 51, 3531–3535. Web of Science CrossRef CAS Google Scholar
Ikeda, S., Toganoh, M., Easwaramoorthi, S., Lim, J. M., Kim, D. & Furuta, H. (2010). J. Org. Chem. 75, 8637–8649. Web of Science CSD CrossRef CAS PubMed Google Scholar
Ito, Y., Amimoto, K. & Kawato, T. (2011). Dyes Pigm. 89, 319–323. Web of Science CSD CrossRef CAS Google Scholar
Lim, C.-K., Seo, J., Kim, S., Kwon, I. C., Ahn, C.-H. & Park, S. Y. (2011). Dyes Pigm. 90, 284–289. Web of Science CrossRef CAS Google Scholar
Lins, G. O. W., Campo, L. F., Rodembusch, F. S. & Stefani, V. (2010). Dyes Pigm. 84, 114-120. Web of Science CrossRef CAS Google Scholar
Maupin, C. M., Castillo, N., Taraphder, S., Tu, C., McKenna, R., Silverman, D. N. & Voth, G. A. (2011). J. Am. Chem. Soc. 133, 6223-6234. Web of Science CrossRef CAS PubMed Google Scholar
Santos, R. C., Silva Faleiro, N. V., Campo, L. F., Scroferneker, M. L., Corbellini, V. A., Rodembusch, F. S. & Stefani, V. (2011). Tetrahedron Lett. 52, 3048–3053. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, K.-C., Chang, M.-J., Lin, T.-Y., Pan, H.-A., Fang, T.-C., Chen, K.-Y., Hung, W.-Y., Hsu, Y.-H. & Chou, P.-T. (2011). J. Am. Chem. Soc. 133, 17738–17745. Web of Science CSD CrossRef CAS PubMed Google Scholar