(E)-4-Allyl-2-[(2-hydroxy­phen­yl)iminiometh­yl]-6-methoxy­phenolate

Eltayeb, N.E.; Teoh, S.G.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S160053681000838X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o934-o935

doi:10.1107/S160053681000838X

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(E)-4-Allyl-2-[(2-hydroxyphenyl)iminiomethyl]-6-methoxyphenolate

Naser Eltaher Eltayeb,^a ‡ Siang Guan Teoh,^a Suchada Chantrapromma ^b § and Hoong-Kun Fun ^c ^*¶

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 3 March 2010; accepted 4 March 2010; online 27 March 2010)

The title compound, C₁₇H₁₇NO₃, crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. The zwitterion exists in a trans configuration about the C=N bond. The dihedral angle between the two benzene rings is 13.42 (7)°. The methoxy group is almost coplanar [C—O—C—C = 2.1 (2)°] with the attached ring whereas the allyl unit is oriented at a dihedral angle of 67.9 (1)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the molecules are linked into zigzag chains along [010] by O—H⋯O hydrogen bonds. In addition, weak C—H⋯π interactions are observed.

Related literature

For background to Schiff bases and their applications, see: Dao et al. (2000 ); Eltayeb & Ahmed (2005a ,b ); Karthikeyan et al. (2006 ); Sriram et al. (2006 ). For related structures, see: Eltayeb et al. (2009 ); Tan & Liu (2009 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₇H₁₇NO₃
M_r = 283.32
Orthorhombic, P b c a
a = 14.719 (3) Å
b = 9.1302 (16) Å
c = 20.597 (4) Å
V = 2768.0 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.50 × 0.15 × 0.02 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.955, T_max = 0.998
16563 measured reflections
4056 independent reflections
2744 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.141
S = 1.00
4056 reflections
254 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2ⁱ	0.95	1.72	2.6443 (16)	166
O1—H1O1⋯O3ⁱ	0.95	2.55	3.1268 (16)	119
N1—H1N1⋯O2	0.97 (2)	1.85 (2)	2.6553 (18)	138 (2)
C14—H14B⋯Cg1ⁱⁱ	1.01 (2)	2.75 (2)	3.569 (2)	139 (2)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000838X/ci5052sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000838X/ci5052Isup2.hkl

checkCIF report

Comment top

Schiff bases have received much attention because of their potential applications. Some of these compounds exhibit various pharmacological activities, as noted by their anticancer (Dao et al., 2000), anti-HIV (Sriram et al., 2006), antibacterial and antifungal (Karthikeyan et al., 2006) properties. In addition, some of them may be used as analytical reagents for the determination of trace elements (Eltayeb & Ahmed, 2005a,b). Previously we have reported the crystal structure of 2-((E)-{2-[(E)-2,3-dihydroxybenzylideneamino]-5-methylphenyl}- iminiomethyl)-6-hydroxyphenolate (Eltayeb et al., 2009) which exists in a zwitterionic form. The title compound is another schiff base which also crystallizes in a zwitterionic form. Herein we report its crystal structure.

The title molecule exists in a trans configuration about the C═N double bond [1.3129 (19) Å], with a C6–N1–C7–C8 torsion angle of 178.13 (14)°. The molecule is slightly twisted, with the dihedral angle between the two benzene rings being 13.42 (7)°. The hydroxy group is coplanar with the attached C1–C6 benzene ring. The methoxy group is coplanar with the attached C8–C13 benzene ring [C14—O3—C12—C11 = 2.1 (2)°; r.m.s. deviation of 0.0384 (1) Å for the eight non H atoms]. The allyl unit (C15–C17) is in an (-)-anticlinal conformation as indicated by the C11—C10—C15—C16 torsion angle of -94.28 (18)°. An intramolecular N—H···O hydrogen bond between the NH⁺ and the phenolate O^- groups generate an S(6) ring motif (Fig. 1 and Table 1) (Bernstein et al., 1995). The bond distances show normal values (Allen et al., 1987) and are comparable with those observed in related structures (Eltayeb et al., 2009; Tan & Liu, 2009).

In the crystal packing (Fig. 2), molecules are linked into zigzag chains along the [010] by O—H···O hydrogen bonds involving hydroxy groups, phenolate and methoxy O atoms (Table 1). Within a chain, the adjacent molecules are approximately perpendicular to each other (Fig. 2). The crystal structure is further stabilized by weak intermolecular C—H···π interactions (Table 1) involving the C8–C13 ring (centroid Cg1).

Related literature top

For background to Schiff bases and their applications, see: Dao et al. (2000); Eltayeb & Ahmed (2005a,b); Karthikeyan et al. (2006); Sriram et al. (2006). For related structures, see: Eltayeb et al. (2009); Tan & Liu (2009). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was synthesized by adding 5-allyl-2-hydroxy-3-methoxybenzaldehyde (0.768 g, 4 mmol) to a solution of 2-aminophenol (0.436 g, 4 mmol) in ethanol (30 ml). The mixture was refluxed with stirring for 30 min. The resultant red solution was filtered and the filtrate was evaporated to give a red solid product. Red plate-shaped single crystals of the title compound suitable for X-ray structure determination were obtained from diethyl ether by slow evaporation at room temperature after a few days.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis, showing chains running along the b axis. Hydrogen bonds are shown as dashed lines.

(E)-4-Allyl-2-[(2-hydroxyphenyl)iminiomethyl]-6-methoxyphenolate top

Crystal data top

C₁₇H₁₇NO₃	F(000) = 1200
M_r = 283.32	D_x = 1.360 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4056 reflections
a = 14.719 (3) Å	θ = 2.0–30.2°
b = 9.1302 (16) Å	µ = 0.09 mm⁻¹
c = 20.597 (4) Å	T = 100 K
V = 2768.0 (9) Å³	Plate, red
Z = 8	0.50 × 0.15 × 0.02 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4056 independent reflections
Radiation source: sealed tube	2744 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 30.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→20
T_min = 0.955, T_max = 0.998	k = −12→12
16563 measured reflections	l = −26→28

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0776P)²] where P = (F_o² + 2F_c²)/3
4056 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₇H₁₇NO₃	V = 2768.0 (9) Å³
M_r = 283.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.719 (3) Å	µ = 0.09 mm⁻¹
b = 9.1302 (16) Å	T = 100 K
c = 20.597 (4) Å	0.50 × 0.15 × 0.02 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	4056 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2744 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.998	R_int = 0.073
16563 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.39 e Å⁻³
4056 reflections	Δρ_min = −0.29 e Å⁻³
254 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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	0.01450 (7)	0.45448 (12)	0.30069 (5)	0.0161 (2)
H1O1	−0.0369	0.3930	0.3044	0.024*
O2	0.12030 (7)	0.76365 (12)	0.20618 (6)	0.0180 (3)
O3	0.15126 (7)	0.93837 (13)	0.10464 (5)	0.0197 (3)
N1	0.18381 (8)	0.56151 (14)	0.28699 (6)	0.0135 (3)
C1	0.07946 (9)	0.39626 (16)	0.33947 (7)	0.0135 (3)
C2	0.06178 (10)	0.28421 (18)	0.38347 (8)	0.0167 (3)
C3	0.13112 (11)	0.22677 (18)	0.42119 (8)	0.0186 (3)
C4	0.21898 (11)	0.28105 (18)	0.41570 (8)	0.0177 (3)
C5	0.23708 (10)	0.39363 (17)	0.37262 (8)	0.0153 (3)
C6	0.16809 (10)	0.45100 (16)	0.33395 (7)	0.0136 (3)
C7	0.26375 (10)	0.60410 (17)	0.26593 (7)	0.0145 (3)
C8	0.27799 (9)	0.71113 (16)	0.21797 (7)	0.0133 (3)
C9	0.36954 (10)	0.74371 (17)	0.20005 (8)	0.0150 (3)
C10	0.38828 (10)	0.84469 (17)	0.15316 (8)	0.0166 (3)
C11	0.31474 (11)	0.91227 (17)	0.12006 (8)	0.0166 (3)
C12	0.22584 (10)	0.88183 (16)	0.13544 (8)	0.0147 (3)
C13	0.20324 (10)	0.78420 (16)	0.18785 (7)	0.0139 (3)
C14	0.16825 (13)	1.03310 (19)	0.05078 (9)	0.0221 (4)
C15	0.48556 (11)	0.8797 (2)	0.13422 (9)	0.0207 (4)
C16	0.52342 (10)	0.77196 (19)	0.08627 (8)	0.0188 (3)
C17	0.55487 (11)	0.8048 (2)	0.02828 (9)	0.0244 (4)
H2	0.0021 (12)	0.247 (2)	0.3859 (8)	0.015 (4)*
H3	0.1195 (13)	0.144 (2)	0.4528 (9)	0.025 (5)*
H4	0.2678 (14)	0.238 (2)	0.4435 (10)	0.031 (5)*
H5	0.2969 (13)	0.435 (2)	0.3707 (9)	0.023 (5)*
H7	0.3152 (12)	0.5554 (19)	0.2862 (8)	0.015 (4)*
H9	0.4179 (13)	0.6900 (19)	0.2254 (8)	0.019 (5)*
H11	0.3273 (13)	0.983 (2)	0.0852 (9)	0.024 (5)*
H14A	0.1109 (14)	1.062 (2)	0.0335 (10)	0.030 (5)*
H14B	0.2011 (14)	1.124 (2)	0.0651 (10)	0.034 (6)*
H14C	0.2072 (13)	0.985 (2)	0.0176 (9)	0.025 (5)*
H15A	0.5199 (14)	0.882 (2)	0.1754 (10)	0.032 (6)*
H15C	0.4901 (12)	0.982 (2)	0.1163 (9)	0.015 (4)*
H16	0.5258 (13)	0.672 (2)	0.1013 (9)	0.029 (5)*
H17A	0.5552 (14)	0.909 (2)	0.0120 (10)	0.033 (5)*
H17B	0.5755 (15)	0.729 (2)	−0.0016 (10)	0.038 (6)*
H1N1	0.1343 (15)	0.611 (2)	0.2647 (10)	0.035 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0080 (5)	0.0182 (6)	0.0222 (6)	−0.0005 (4)	−0.0012 (4)	0.0024 (5)
O2	0.0091 (5)	0.0203 (6)	0.0246 (6)	0.0008 (4)	0.0019 (4)	0.0038 (5)
O3	0.0153 (5)	0.0214 (6)	0.0223 (6)	0.0032 (4)	−0.0001 (4)	0.0063 (5)
N1	0.0101 (6)	0.0140 (6)	0.0164 (7)	−0.0008 (5)	−0.0003 (5)	0.0008 (5)
C1	0.0091 (6)	0.0140 (7)	0.0173 (8)	0.0023 (5)	−0.0004 (5)	−0.0023 (6)
C2	0.0127 (7)	0.0170 (8)	0.0204 (8)	−0.0020 (6)	0.0014 (6)	0.0011 (6)
C3	0.0170 (7)	0.0177 (8)	0.0211 (8)	0.0006 (6)	0.0012 (6)	0.0030 (6)
C4	0.0155 (7)	0.0180 (8)	0.0196 (8)	0.0018 (6)	−0.0026 (6)	0.0004 (6)
C5	0.0106 (6)	0.0174 (8)	0.0178 (8)	−0.0006 (5)	−0.0019 (5)	−0.0006 (6)
C6	0.0118 (6)	0.0128 (7)	0.0162 (8)	−0.0006 (5)	0.0015 (5)	−0.0007 (6)
C7	0.0100 (6)	0.0150 (7)	0.0186 (8)	0.0003 (5)	−0.0006 (5)	−0.0020 (6)
C8	0.0104 (6)	0.0133 (7)	0.0164 (8)	−0.0013 (5)	0.0011 (5)	−0.0024 (6)
C9	0.0104 (6)	0.0148 (7)	0.0198 (8)	−0.0018 (5)	0.0006 (5)	−0.0016 (6)
C10	0.0124 (7)	0.0160 (7)	0.0213 (8)	−0.0035 (6)	0.0031 (6)	−0.0040 (6)
C11	0.0179 (7)	0.0139 (7)	0.0181 (8)	−0.0019 (6)	0.0034 (6)	−0.0008 (6)
C12	0.0139 (7)	0.0128 (7)	0.0175 (8)	0.0012 (5)	0.0007 (5)	−0.0007 (6)
C13	0.0109 (7)	0.0128 (7)	0.0181 (8)	−0.0003 (5)	0.0014 (5)	−0.0024 (6)
C14	0.0270 (9)	0.0183 (8)	0.0212 (9)	0.0041 (7)	−0.0001 (7)	0.0047 (7)
C15	0.0136 (7)	0.0254 (9)	0.0230 (9)	−0.0066 (6)	0.0031 (6)	−0.0021 (7)
C16	0.0098 (6)	0.0199 (8)	0.0268 (9)	0.0020 (6)	−0.0003 (6)	0.0013 (7)
C17	0.0148 (8)	0.0326 (10)	0.0259 (9)	0.0016 (7)	0.0002 (6)	−0.0065 (8)

Geometric parameters (Å, º) top

O1—C1	1.3546 (17)	C8—C13	1.428 (2)
O1—H1O1	0.9454	C8—C9	1.4285 (19)
O2—C13	1.2915 (17)	C9—C10	1.363 (2)
O3—C12	1.3691 (18)	C9—H9	1.010 (18)
O3—C14	1.429 (2)	C10—C11	1.420 (2)
N1—C7	1.3129 (19)	C10—C15	1.518 (2)
N1—C6	1.4168 (19)	C11—C12	1.375 (2)
N1—H1N1	0.97 (2)	C11—H11	0.982 (19)
C1—C2	1.391 (2)	C12—C13	1.439 (2)
C1—C6	1.4015 (19)	C14—H14A	0.95 (2)
C2—C3	1.386 (2)	C14—H14B	1.01 (2)
C2—H2	0.944 (18)	C14—H14C	0.99 (2)
C3—C4	1.390 (2)	C15—C16	1.501 (2)
C3—H3	1.010 (19)	C15—H15A	0.99 (2)
C4—C5	1.384 (2)	C15—H15C	1.003 (19)
C4—H4	1.00 (2)	C16—C17	1.316 (2)
C5—C6	1.393 (2)	C16—H16	0.96 (2)
C5—H5	0.960 (19)	C17—H17A	1.01 (2)
C7—C8	1.405 (2)	C17—H17B	0.98 (2)
C7—H7	0.972 (18)

C1—O1—H1O1	106.5	C8—C9—H9	115.5 (10)
C12—O3—C14	116.60 (12)	C9—C10—C11	118.66 (14)
C7—N1—C6	125.65 (13)	C9—C10—C15	121.01 (14)
C7—N1—H1N1	112.1 (13)	C11—C10—C15	120.27 (15)
C6—N1—H1N1	122.2 (13)	C12—C11—C10	121.80 (15)
O1—C1—C2	122.72 (13)	C12—C11—H11	118.7 (12)
O1—C1—C6	117.99 (13)	C10—C11—H11	119.5 (12)
C2—C1—C6	119.29 (13)	O3—C12—C11	125.46 (14)
C3—C2—C1	120.38 (14)	O3—C12—C13	113.32 (13)
C3—C2—H2	121.2 (11)	C11—C12—C13	121.22 (14)
C1—C2—H2	118.4 (11)	O2—C13—C8	122.23 (14)
C2—C3—C4	120.32 (15)	O2—C13—C12	121.86 (13)
C2—C3—H3	121.3 (11)	C8—C13—C12	115.91 (13)
C4—C3—H3	118.4 (11)	O3—C14—H14A	107.5 (12)
C5—C4—C3	119.76 (14)	O3—C14—H14B	110.9 (12)
C5—C4—H4	121.5 (12)	H14A—C14—H14B	108.0 (17)
C3—C4—H4	118.7 (12)	O3—C14—H14C	111.6 (11)
C4—C5—C6	120.37 (14)	H14A—C14—H14C	111.9 (16)
C4—C5—H5	119.9 (12)	H14B—C14—H14C	106.9 (16)
C6—C5—H5	119.7 (12)	C16—C15—C10	112.41 (13)
C5—C6—C1	119.88 (14)	C16—C15—H15A	113.0 (12)
C5—C6—N1	122.62 (13)	C10—C15—H15A	105.5 (12)
C1—C6—N1	117.48 (13)	C16—C15—H15C	109.9 (10)
N1—C7—C8	124.88 (14)	C10—C15—H15C	110.7 (10)
N1—C7—H7	114.9 (10)	H15A—C15—H15C	105.0 (16)
C8—C7—H7	120.2 (10)	C17—C16—C15	125.35 (17)
C7—C8—C13	121.01 (13)	C17—C16—H16	119.6 (12)
C7—C8—C9	117.85 (13)	C15—C16—H16	115.0 (12)
C13—C8—C9	121.15 (14)	C16—C17—H17A	121.2 (12)
C10—C9—C8	120.97 (14)	C16—C17—H17B	121.3 (12)
C10—C9—H9	123.5 (10)	H17A—C17—H17B	117.4 (17)

O1—C1—C2—C3	178.84 (14)	C8—C9—C10—C15	179.82 (14)
C6—C1—C2—C3	−0.3 (2)	C9—C10—C11—C12	2.0 (2)
C1—C2—C3—C4	0.3 (2)	C15—C10—C11—C12	179.24 (15)
C2—C3—C4—C5	0.4 (2)	C14—O3—C12—C11	2.1 (2)
C3—C4—C5—C6	−1.1 (2)	C14—O3—C12—C13	−178.25 (13)
C4—C5—C6—C1	1.1 (2)	C10—C11—C12—O3	−177.77 (14)
C4—C5—C6—N1	−177.01 (14)	C10—C11—C12—C13	2.6 (2)
O1—C1—C6—C5	−179.60 (14)	C7—C8—C13—O2	5.1 (2)
C2—C1—C6—C5	−0.4 (2)	C9—C8—C13—O2	−175.35 (14)
O1—C1—C6—N1	−1.4 (2)	C7—C8—C13—C12	−174.61 (14)
C2—C1—C6—N1	177.85 (13)	C9—C8—C13—C12	5.0 (2)
C7—N1—C6—C5	12.8 (2)	O3—C12—C13—O2	−5.3 (2)
C7—N1—C6—C1	−165.40 (14)	C11—C12—C13—O2	174.39 (14)
C6—N1—C7—C8	178.13 (14)	O3—C12—C13—C8	174.40 (12)
N1—C7—C8—C13	0.3 (2)	C11—C12—C13—C8	−5.9 (2)
N1—C7—C8—C9	−179.33 (14)	C9—C10—C15—C16	82.87 (19)
C7—C8—C9—C10	178.97 (14)	C11—C10—C15—C16	−94.28 (18)
C13—C8—C9—C10	−0.6 (2)	C10—C15—C16—C17	121.37 (18)
C8—C9—C10—C11	−3.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.95	1.72	2.6443 (16)	166
O1—H1O1···O3ⁱ	0.95	2.55	3.1268 (16)	119
N1—H1N1···O2	0.97 (2)	1.85 (2)	2.6553 (18)	138 (2)
C14—H14B···Cg1ⁱⁱ	1.01 (2)	2.75 (2)	3.569 (2)	139 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₃
M_r	283.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	14.719 (3), 9.1302 (16), 20.597 (4)
V (Å³)	2768.0 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.15 × 0.02

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.955, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	16563, 4056, 2744
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.141, 1.00
No. of reflections	4056
No. of parameters	254
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.95	1.72	2.6443 (16)	166
O1—H1O1···O3ⁱ	0.95	2.55	3.1268 (16)	119
N1—H1N1···O2	0.97 (2)	1.85 (2)	2.6553 (18)	138 (2)
C14—H14B···Cg1ⁱⁱ	1.01 (2)	2.75 (2)	3.569 (2)	139 (2)

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

Footnotes

‡On study leave from Department of Chemistry, International University of Africa, Khartoum, Sudan, e-mail: nasertaha90@hotmail.com

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors thank the Malaysian Government, the Ministry of Science, Technology and Innovation (MOSTI) and Universiti Sains Malaysia for the E-Science Fund and RU research grants (PKIMIA/613308, PKIMIA/815002, and PKIMIA/811120). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing study leave. The authors also thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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Volume 66| Part 4| April 2010| Pages o934-o935

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