2-(7-Hydr­oxy-2-naphth­yloxy)-N-(6-methyl-2-pyrid­yl)acetamide

Fun, H.-K.; Jebas, S.R.; Jana, S.; Chakrabarty, R.; Goswami, S.

doi:10.1107/S1600536808006211

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o699

doi:10.1107/S1600536808006211

Open

access

2-(7-Hydroxy-2-naphthyloxy)-N-(6-methyl-2-pyridyl)acetamide

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ Subrata Jana,^b Rinku Chakrabarty ^b and Shyamaprasad Goswami ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Chemistry, Bengal Engineering and Science University, Shibpur, Howrah 711 103, India
^*Correspondence e-mail: hkfun@usm.my

(Received 5 March 2008; accepted 6 March 2008; online 12 March 2008)

In the title compound, C₁₈H₁₆N₂O₃, the dihedral angle between the naphthalene ring system and the pyridyl ring is 18.1 (8)°. The molecules are interconnected via C—H⋯O and O—H⋯O hydrogen bonds. Inversion-related molecules are linked by O—H⋯O hydrogen bonds into cyclic centrosymmetric R₂²(22) dimers. Intramolecular N—H⋯O hydrogen bonding produces an S(5) ring motif. The crystal structure is further stabilized by weak C—H—π interactions.

Related literature

For related literature on the applications; see: Atwood et al. (1996 ); Garcia-Tellado et al. (1990 ); Ghosh & Masanta (2006 ). For comparison bond lengths and angles see: Jin & Jin (2005 ); Liu & Li (2004 ); Rozycka-Sokolowska et al. (2004 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₃
M_r = 308.33
Triclinic, $[P \overline 1]$
a = 5.3676 (3) Å
b = 11.6991 (7) Å
c = 12.2915 (6) Å
α = 104.994 (4)°
β = 94.777 (3)°
γ = 94.877 (4)°
V = 738.42 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100.0 (1) K
0.4 × 0.16 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.963, T_max = 0.992
12299 measured reflections
3340 independent reflections
2480 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.130
S = 1.08
3340 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11B⋯O3ⁱ	0.97	2.45	3.410 (2)	168
N1—H1N1⋯O1	0.88 (2)	2.11 (2)	2.5688 (18)	111.9 (16)
O3—H1O3⋯O2ⁱⁱ	0.88 (3)	1.85 (2)	2.6575 (17)	152 (2)
C11—H11A⋯Cg1ⁱⁱⁱ	0.97	2.63	3.438	141
C18—H18A⋯Cg2^iv	0.97	2.92	3.805	153
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x, -y+1, -z+2; (iii) x-1, y, z; (iv) -x, -y+1, -z+1. Cg1 is the centroid of the C1,C2,C7–C10 ring and Cg2 is the centroid of C2–C7 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006211/ng2430sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808006211/ng2430Isup2.hkl

checkCIF report

Comment top

Pyridine amide moiety is widely used for the recognition of carboxylic acid functional group due to its complementary donor-acceptor arrangement (Garcia-Tellado et al., 1990). This group attached with different spacer having photo physical properties is the current interest for the recognition studies of both mono/di carboxylic acids (Ghosh & Masanta, 2006).This type of compounds is also important for its unique supramolecular arrangement (Atwood et al., 1996).

The asymmetric unit of (I) contains one molecule of 2–(7-hydroxy– naphthalene-2-yloxy)-N-(6-methyl-pyridine–2–yl) –acetamide. The dihedral angle between the naphthalene ring and the pyridine rings being 18.03 (8)°. The bond lengths and bond angles are comparable with the values reported in the literature (Rozycka-Sokolowska et al., 2004; Jin & Jin, 2005). The bond distance of C12=O2 is 1.226 (2) Å, which is typical for double bonds (Liu & Li., 2004). The naphthalene ring is planar, the maximum deviation from the least squares plane being -0.011 (2) Å for atom C10. The pyridine ring is planar with the maximum deviation from planarity being -0.010 (2) Å for atom C17.

The molecules are stacked into layers parallel to the bc-plane by C11—H11B—O3ⁱ and O3—H1O3—O2ⁱⁱ hydrogen bonds (Fig. 2). In the crystal structure of (I), inversion-related molecules at (x,y,z) and (2 - x,1 - y,3 - z) are linked by O3—H1O3—O2 hydrogen bonds into cyclic centrosymmetric R₂²(22) dimers. The crystal structure is further stabilized by weak C—H—π interactions involving rings C11—H11A—Cg1 (where Cg1 is the centroid of the C1,C2,C7—C10 ring) and C18—H18A—Cg2 (where Cg2 is the centroid of C2—C7 ring). The molecular conformation is stabilized by a N1—H1N1—O1 intramolecular interaction generating a ring motif S(5).

Related literature top

For related literature on the applications; see: Atwood et al. (1996); Garcia-Tellado et al. (1990); Ghosh & Masanta (2006). For comparison bond lengths and angles see: Jin & Jin (2005); Liu & Li (2004); Rozycka-Sokolowska et al. (2004). Cg1 is the centroid of the C1,C2,C7–C10 ring and Cg2 is the centroid of C2–C7 ring

Experimental top

2,7-Dihydroxynaphthalene (160 mg, 1.0 mmol) and N–picolylchloroacetamide (185 mg, 1.0 mmol) were stirred with K₂CO₃ (345 mg, 2.5 mmol) and ^tBu4N⁺Br^- (50 mg, 0.16 mmol) in dry acetone (10 ml) for 7 h at room temperature. Acetone was then distilled off and the crude product was extracted with CHCl₃ (4 x 20 ml) after washing with water. The product (I) was purified by column chromatography (Silica gel 100–200 mesh) using 20% ethyl acetate in pet ether as eluent to afford an off-white coloured solid compound (Yield 61%). Single crystals were grown by slow evaporation of CHCl₃/MeOH/Xylene solution (v/v 1:1:3) (Mp. 178–80 °C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

2-(7-Hydroxy-2-naphthyloxy)-N-(6-methyl-2-pyridyl)acetamide top

Crystal data top

C₁₈H₁₆N₂O₃	Z = 2
M_r = 308.33	F(000) = 324
Triclinic, P1	D_x = 1.387 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3676 (3) Å	Cell parameters from 2511 reflections
b = 11.6991 (7) Å	θ = 3.4–30.4°
c = 12.2915 (6) Å	µ = 0.10 mm⁻¹
α = 104.994 (4)°	T = 100 K
β = 94.777 (3)°	Block, colourless
γ = 94.877 (4)°	0.4 × 0.16 × 0.09 mm
V = 738.42 (7) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2480 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	R_int = 0.046
ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −6→6
T_min = 0.963, T_max = 0.992	k = −15→13
12299 measured reflections	l = −15→15
3340 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.045	w = 1/[σ²(F_o²) + (0.0577P)² + 0.2187P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.130	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.24 e Å⁻³
3340 reflections	Δρ_min = −0.31 e Å⁻³
217 parameters

Crystal data top

C₁₈H₁₆N₂O₃	γ = 94.877 (4)°
M_r = 308.33	V = 738.42 (7) Å³
Triclinic, P1	Z = 2
a = 5.3676 (3) Å	Mo Kα radiation
b = 11.6991 (7) Å	µ = 0.10 mm⁻¹
c = 12.2915 (6) Å	T = 100 K
α = 104.994 (4)°	0.4 × 0.16 × 0.09 mm
β = 94.777 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3340 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2480 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.992	R_int = 0.046
12299 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.24 e Å⁻³
3340 reflections	Δρ_min = −0.31 e Å⁻³
217 parameters

Special details top

Geometry. Experimental. The low-temperature data was collected with the Oxford Crysosystem Cobra low-temperature attachement.

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.

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

	x	y	z	U_iso*/U_eq
O1	−0.0438 (2)	0.40705 (11)	0.65093 (10)	0.0240 (3)
O2	−0.5889 (2)	0.23059 (11)	0.67844 (10)	0.0252 (3)
O3	0.8081 (2)	0.77389 (11)	1.13643 (11)	0.0245 (3)
N1	−0.3537 (3)	0.23114 (14)	0.53179 (13)	0.0225 (3)
N2	−0.3711 (3)	0.13147 (13)	0.34601 (12)	0.0204 (3)
C1	0.2212 (3)	0.52560 (15)	0.81993 (14)	0.0202 (4)
H1A	0.1222	0.4975	0.8681	0.024*
C2	0.4376 (3)	0.60921 (15)	0.86540 (14)	0.0188 (4)
C3	0.5095 (3)	0.65141 (15)	0.98390 (14)	0.0201 (4)
H3A	0.4128	0.6258	1.0342	0.024*
C4	0.7222 (3)	0.73013 (15)	1.02417 (14)	0.0199 (4)
C5	0.8699 (3)	0.77091 (16)	0.94921 (15)	0.0222 (4)
H5A	1.0129	0.8245	0.9777	0.027*
C6	0.8034 (3)	0.73183 (15)	0.83490 (15)	0.0220 (4)
H6A	0.9019	0.759	0.786	0.026*
C7	0.5856 (3)	0.65024 (15)	0.79020 (14)	0.0194 (4)
C8	0.5140 (3)	0.60795 (16)	0.67167 (15)	0.0218 (4)
H8A	0.6104	0.6349	0.622	0.026*
C9	0.3063 (3)	0.52862 (16)	0.62984 (15)	0.0219 (4)
H9A	0.2608	0.5019	0.5521	0.026*
C10	0.1598 (3)	0.48687 (15)	0.70512 (15)	0.0212 (4)
C11	−0.2068 (3)	0.35993 (16)	0.71767 (15)	0.0214 (4)
H11A	−0.2874	0.4234	0.7641	0.026*
H11B	−0.111	0.3235	0.7675	0.026*
C12	−0.4042 (3)	0.26785 (15)	0.64022 (14)	0.0201 (4)
C13	−0.4891 (3)	0.14402 (15)	0.43903 (15)	0.0206 (4)
C14	−0.7171 (3)	0.08120 (16)	0.44454 (16)	0.0241 (4)
H14A	−0.7945	0.0941	0.511	0.029*
C15	−0.8235 (3)	−0.00193 (17)	0.34564 (16)	0.0259 (4)
H15A	−0.9753	−0.0469	0.3448	0.031*
C16	−0.7042 (3)	−0.01777 (16)	0.24877 (15)	0.0227 (4)
H16A	−0.7733	−0.0742	0.1826	0.027*
C17	−0.4792 (3)	0.05155 (15)	0.25079 (14)	0.0198 (4)
C18	−0.3482 (3)	0.04513 (16)	0.14692 (15)	0.0244 (4)
H18D	−0.1719	0.0416	0.1646	0.037*
H18A	−0.3712	0.1145	0.1209	0.037*
H18B	−0.4174	−0.0248	0.0887	0.037*
H1N1	−0.210 (4)	0.2626 (18)	0.5165 (17)	0.026 (5)*
H1O3	0.700 (5)	0.756 (2)	1.181 (2)	0.043 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0247 (6)	0.0271 (7)	0.0162 (6)	−0.0067 (5)	0.0001 (5)	0.0022 (5)
O2	0.0267 (6)	0.0274 (7)	0.0193 (7)	−0.0016 (5)	0.0039 (5)	0.0034 (5)
O3	0.0262 (6)	0.0291 (7)	0.0146 (7)	−0.0054 (5)	−0.0010 (5)	0.0031 (5)
N1	0.0234 (7)	0.0243 (8)	0.0165 (8)	−0.0042 (6)	0.0005 (6)	0.0021 (6)
N2	0.0226 (7)	0.0195 (7)	0.0174 (8)	−0.0006 (5)	−0.0010 (6)	0.0037 (6)
C1	0.0224 (8)	0.0214 (9)	0.0162 (9)	0.0007 (6)	0.0028 (7)	0.0042 (7)
C2	0.0210 (8)	0.0170 (8)	0.0174 (9)	0.0027 (6)	0.0020 (7)	0.0025 (7)
C3	0.0233 (8)	0.0205 (9)	0.0161 (9)	0.0001 (6)	0.0028 (7)	0.0048 (7)
C4	0.0233 (8)	0.0186 (9)	0.0159 (9)	0.0019 (6)	−0.0002 (7)	0.0020 (7)
C5	0.0219 (8)	0.0213 (9)	0.0211 (10)	−0.0015 (6)	0.0010 (7)	0.0035 (7)
C6	0.0238 (8)	0.0210 (9)	0.0207 (9)	−0.0011 (7)	0.0047 (7)	0.0051 (7)
C7	0.0231 (8)	0.0177 (8)	0.0168 (9)	0.0021 (6)	0.0022 (7)	0.0035 (7)
C8	0.0258 (8)	0.0216 (9)	0.0187 (9)	0.0034 (7)	0.0050 (7)	0.0058 (7)
C9	0.0281 (9)	0.0226 (9)	0.0133 (9)	0.0028 (7)	0.0008 (7)	0.0021 (7)
C10	0.0219 (8)	0.0182 (9)	0.0203 (9)	0.0021 (6)	−0.0012 (7)	0.0004 (7)
C11	0.0239 (8)	0.0219 (9)	0.0167 (9)	0.0009 (7)	0.0003 (7)	0.0031 (7)
C12	0.0241 (8)	0.0196 (9)	0.0158 (9)	0.0027 (7)	−0.0001 (7)	0.0038 (7)
C13	0.0241 (8)	0.0195 (9)	0.0165 (9)	0.0008 (6)	−0.0013 (7)	0.0033 (7)
C14	0.0251 (9)	0.0277 (10)	0.0186 (9)	−0.0014 (7)	0.0022 (7)	0.0062 (8)
C15	0.0240 (8)	0.0277 (10)	0.0241 (10)	−0.0060 (7)	−0.0029 (7)	0.0082 (8)
C16	0.0257 (8)	0.0205 (9)	0.0183 (9)	−0.0032 (7)	−0.0038 (7)	0.0028 (7)
C17	0.0233 (8)	0.0183 (8)	0.0168 (9)	0.0022 (6)	−0.0012 (7)	0.0039 (7)
C18	0.0272 (9)	0.0243 (9)	0.0183 (9)	0.0000 (7)	−0.0001 (7)	0.0016 (7)

Geometric parameters (Å, º) top

O1—C10	1.376 (2)	C6—H6A	0.93
O1—C11	1.419 (2)	C7—C8	1.420 (2)
O2—C12	1.226 (2)	C8—C9	1.360 (2)
O3—C4	1.366 (2)	C8—H8A	0.93
O3—H1O3	0.88 (3)	C9—C10	1.415 (3)
N1—C12	1.348 (2)	C9—H9A	0.93
N1—C13	1.415 (2)	C11—C12	1.516 (2)
N1—H1N1	0.88 (2)	C11—H11A	0.97
N2—C13	1.334 (2)	C11—H11B	0.97
N2—C17	1.345 (2)	C13—C14	1.389 (2)
C1—C10	1.368 (2)	C14—C15	1.388 (2)
C1—C2	1.426 (2)	C14—H14A	0.93
C1—H1A	0.93	C15—C16	1.377 (3)
C2—C7	1.415 (2)	C15—H15A	0.93
C2—C3	1.420 (2)	C16—C17	1.391 (2)
C3—C4	1.374 (2)	C16—H16A	0.93
C3—H3A	0.93	C17—C18	1.496 (3)
C4—C5	1.411 (2)	C18—H18D	0.96
C5—C6	1.366 (2)	C18—H18A	0.96
C5—H5A	0.93	C18—H18B	0.96
C6—C7	1.418 (2)

C10—O1—C11	118.54 (13)	C1—C10—O1	125.35 (16)
C4—O3—H1O3	112.9 (16)	C1—C10—C9	121.31 (16)
C12—N1—C13	129.91 (15)	O1—C10—C9	113.33 (15)
C12—N1—H1N1	115.8 (13)	O1—C11—C12	109.16 (14)
C13—N1—H1N1	114.2 (13)	O1—C11—H11A	109.8
C13—N2—C17	117.79 (14)	C12—C11—H11A	109.8
C10—C1—C2	119.74 (17)	O1—C11—H11B	109.8
C10—C1—H1A	120.1	C12—C11—H11B	109.8
C2—C1—H1A	120.1	H11A—C11—H11B	108.3
C7—C2—C3	119.23 (15)	O2—C12—N1	125.19 (16)
C7—C2—C1	119.02 (15)	O2—C12—C11	120.00 (15)
C3—C2—C1	121.74 (16)	N1—C12—C11	114.78 (15)
C4—C3—C2	119.93 (16)	N2—C13—C14	124.72 (16)
C4—C3—H3A	120	N2—C13—N1	111.27 (15)
C2—C3—H3A	120	C14—C13—N1	124.00 (17)
O3—C4—C3	124.03 (16)	C15—C14—C13	116.46 (17)
O3—C4—C5	115.14 (15)	C15—C14—H14A	121.8
C3—C4—C5	120.83 (16)	C13—C14—H14A	121.8
C6—C5—C4	120.17 (15)	C16—C15—C14	120.03 (16)
C6—C5—H5A	119.9	C16—C15—H15A	120
C4—C5—H5A	119.9	C14—C15—H15A	120
C5—C6—C7	120.59 (17)	C15—C16—C17	119.32 (16)
C5—C6—H6A	119.7	C15—C16—H16A	120.3
C7—C6—H6A	119.7	C17—C16—H16A	120.3
C2—C7—C6	119.24 (15)	N2—C17—C16	121.65 (16)
C2—C7—C8	119.26 (15)	N2—C17—C18	116.05 (15)
C6—C7—C8	121.50 (16)	C16—C17—C18	122.26 (15)
C9—C8—C7	120.91 (17)	C17—C18—H18D	109.5
C9—C8—H8A	119.5	C17—C18—H18A	109.5
C7—C8—H8A	119.5	H18D—C18—H18A	109.5
C8—C9—C10	119.75 (16)	C17—C18—H18B	109.5
C8—C9—H9A	120.1	H18D—C18—H18B	109.5
C10—C9—H9A	120.1	H18A—C18—H18B	109.5

C10—C1—C2—C7	−0.2 (2)	C11—O1—C10—C9	−179.27 (14)
C10—C1—C2—C3	−179.63 (16)	C8—C9—C10—C1	0.7 (3)
C7—C2—C3—C4	−0.7 (3)	C8—C9—C10—O1	−179.89 (15)
C1—C2—C3—C4	178.70 (16)	C10—O1—C11—C12	−175.79 (14)
C2—C3—C4—O3	−178.86 (15)	C13—N1—C12—O2	−1.0 (3)
C2—C3—C4—C5	0.6 (3)	C13—N1—C12—C11	177.16 (16)
O3—C4—C5—C6	179.21 (16)	O1—C11—C12—O2	−167.56 (15)
C3—C4—C5—C6	−0.3 (3)	O1—C11—C12—N1	14.2 (2)
C4—C5—C6—C7	0.1 (3)	C17—N2—C13—C14	−0.6 (3)
C3—C2—C7—C6	0.5 (2)	C17—N2—C13—N1	−179.81 (14)
C1—C2—C7—C6	−178.93 (15)	C12—N1—C13—N2	−178.05 (16)
C3—C2—C7—C8	179.92 (16)	C12—N1—C13—C14	2.7 (3)
C1—C2—C7—C8	0.5 (2)	N2—C13—C14—C15	1.4 (3)
C5—C6—C7—C2	−0.2 (3)	N1—C13—C14—C15	−179.45 (16)
C5—C6—C7—C8	−179.62 (16)	C13—C14—C15—C16	−0.6 (3)
C2—C7—C8—C9	−0.2 (3)	C14—C15—C16—C17	−1.0 (3)
C6—C7—C8—C9	179.21 (16)	C13—N2—C17—C16	−1.1 (2)
C7—C8—C9—C10	−0.4 (3)	C13—N2—C17—C18	176.69 (15)
C2—C1—C10—O1	−179.74 (15)	C15—C16—C17—N2	1.9 (3)
C2—C1—C10—C9	−0.4 (3)	C15—C16—C17—C18	−175.75 (17)
C11—O1—C10—C1	0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O3ⁱ	0.97	2.45	3.410 (2)	168
N1—H1N1···O1	0.88 (2)	2.11 (2)	2.5688 (18)	111.9 (16)
O3—H1O3···O2ⁱⁱ	0.88 (3)	1.85 (2)	2.6575 (17)	152 (2)
C11—H11A···Cg1ⁱⁱⁱ	0.97	2.63	3.438	141
C18—H18A···Cg2^iv	0.97	2.93	3.805	153

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₃
M_r	308.33
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.3676 (3), 11.6991 (7), 12.2915 (6)
α, β, γ (°)	104.994 (4), 94.777 (3), 94.877 (4)
V (Å³)	738.42 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.4 × 0.16 × 0.09

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.963, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	12299, 3340, 2480
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.130, 1.08
No. of reflections	3340
No. of parameters	217
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.31

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11B···O3ⁱ	0.97	2.45	3.410 (2)	168.2
N1—H1N1···O1	0.88 (2)	2.11 (2)	2.5688 (18)	111.9 (16)
O3—H1O3···O2ⁱⁱ	0.88 (3)	1.85 (2)	2.6575 (17)	152 (2)
C11—H11A···Cg1ⁱⁱⁱ	0.97	2.631	3.438	140.85
C18—H18A···Cg2^iv	0.97	2.925	3.805	152.91

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

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India

Acknowledgements

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for the awarding of a post-doctoral research fellowship. SG thanks the CSIR and DST for financial support. RC thanks the CSIR for a research fellowship.

References

Atwood, J. L., Davies, J. E. D., MacNico, D. D. & Vogtle, F. (1996). Editors. Comprehensive Supramolecular Chemistry, Vols. 6, 7, 9. Oxford: Pergamon. Google Scholar
Bruker (2005). SAINT and SMART. Bruker Axs Inc., Madison, Wisconsin, USA. Google Scholar
Garcia-Tellado, F., Goswami, S., Chang, S. K., Geib, S. J. & Hamilton, A. D. (1990). J. Am. Chem. Soc. 112, 7393–7394. CSD CrossRef CAS Web of Science Google Scholar
Ghosh, K. & Masanta, G. (2006). Tetrahedron Lett. 47, 2365–2369. Web of Science CrossRef CAS Google Scholar
Jin, C.-Z. & Jin, L.-F. (2005). Acta Cryst. E61, o275–o276. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, W.-Y. & Li, Y.-Z. (2004). Acta Cryst. E60, o694–o695. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rozycka-Sokolowska, E., Marciniak, B. & Pavlyuk, V. (2004). Acta Cryst. E60, o884–o885. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar