(E)-N′-(3-Eth­oxy-4-hy­droxy­benzyl­idene)-4-meth­oxy­benzohydrazide

Fun, H.-K.; Promdet, P.; Horkaew, J.; Karalai, C.; Chantrapromma, S.

doi:10.1107/S1600536812007374

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o849-o850

doi:10.1107/S1600536812007374

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(E)-N′-(3-Ethoxy-4-hydroxybenzylidene)-4-methoxybenzohydrazide

Hoong-Kun Fun,^a ^*‡ Premrudee Promdet,^b Jirapa Horkaew,^b Chatchanok Karalai ^b and Suchada Chantrapromma ^b §

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

(Received 14 February 2012; accepted 18 February 2012; online 24 February 2012)

In the molecule of the title benzohydrazide derivative, C₁₇H₁₈N₂O₄, the dihedral angle between the two benzene rings is 6.86 (11)°. The methoxy group of the 4-methoxyphenyl fragment deviates slightly [C_methyl—O—C—C = 10.0 (4)°] with respect to the benzene ring, whereas the ethoxy group of the 3-ethoxy-4-hydroxyphenyl fragment is almost coplanar [C—O—C—C_methyl = 178.5 (2)°]. In the crystal, molecules are linked by N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds into a two-dimensional network parallel to the ab plane. C—H⋯π interactions and C⋯O [2.980 (3) Å] short contacts are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures, see: Fun et al. (2011 ); Horkaew et al. (2011 ); Promdet et al. (2011 ). For background and applications to benzohydrazide derivatives, see: Bedia et al. (2006 ); Loncle et al. (2004 ); Raj et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₄
M_r = 314.33
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.0607 (9) Å
b = 11.086 (2) Å
c = 27.629 (5) Å
V = 1550.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 297 K
0.56 × 0.10 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.948, T_max = 0.993
10252 measured reflections
2637 independent reflections
1921 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.154
S = 1.04
2637 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O3	0.82	2.41	2.683 (2)	100
O4—H1O4⋯O1ⁱ	0.82	2.21	2.981 (2)	156
N1—H1N1⋯O1ⁱⁱ	0.90	2.10	2.994 (3)	172
C10—H10A⋯O4ⁱⁱⁱ	0.93	2.55	3.462 (3)	168
C16—H16B⋯Cg1ⁱ	0.97	2.68	3.499 (2)	142
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812007374/rz2713sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007374/rz2713Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007374/rz2713Isup3.cml

checkCIF report

Comment top

During the course of our on-going research on benzohydrazide derivatives, which have been reported to possess various biological properties such as antibacterial and antifungal (Loncle et al., 2004), antitubercular (Bedia et al., 2006) and antiproliferative (Raj et al., 2007) activities, the synthesis and crystal structures of benzohydrazide derivatives have been reported (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). The title compound was synthesized and tested for its antioxidant and antibacterial activities and found to be inactive.

The molecule of the title benzohydrazide derivative (Fig. 1) exists in a trans-configuration with respect to the C8═N2 bond [1.286 (4) Å], as indicated by the torsion angle N1–N2–C8–C9 = -178.2 (2)°. The molecule is slightly twisted with the dihedral angle between the two benzene rings of 6.86 (11)°. The middle bridge fragment (O1/C7/N1/N2/C8) is planar with the torsion angle N2–N1–C7–O1 = 0.8 (4)° and the r.m.s. of 0.0360 (2) Å for the five non-H atoms. The mean plane through this bridge makes dihedral angles of 28.94 (15) and 26.51 (15)° with the C1–C6 and C9–C14 phenyl rings, respectively. The methoxy group of 4-methoxyphenyl is slightly twisted with respect to its bound benzene ring [torsion angle C15–O2–C4–C5 = 10.0 (4)°], whereas the ethoxy group of 3-ethoxy-4-hydroxyphenyl is co-planar with the torsion angle C11–O3–C16–C17 = 178.5 (2)°.

An intramolecular O4—H1O4···O3 hydrogen bond generates a S(5) ring motif (Bernstein et al., 1995). Bond distances are of normal values (Allen et al., 1987) and are comparable with those found in related structures (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O and O—H···O hydrogen bonds and weak C—H···O interactions (Table 1) into a two-dimensional network paralell to the ab plane. The crystal is further stabilized by C—H···π weak interaction (Table 1). A C8···O4^iv [2.980 (3) Å: (iv) = -x, 1/2+y, 1/2+z] short contact was observed.

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures, see: Fun et al. (2011); Horkaew et al. (2011); Promdet et al. (2011). For background and applications to benzohydrazide derivatives, see: Bedia et al. (2006); Loncle et al. (2004); Raj et al. (2007).

Experimental top

The title compound was prepared by dissolving 4-methoxybenzohydrazide (2 mmol, 0.33 g) in ethanol (10 ml). A solution of 3-ethoxy-4-hydroxybenzaldehyde (2 mmol, 0.33 g) in ethanol (10 ml) was then added slowly to the reaction. The mixture was refluxed for about 5 h and a white solid appeared. The mixture was then cooled to room temperature and filtered. Colourless needle-shaped single crystals of the title compound suitable for X-ray structure determination were recrystallized from methanol by slow evaporation of the solvent at room temperature after several days. M. p. 486-488 K.

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, showing 45% probability displacement ellipsoids. Hydrogen bond are drawn as dashed line.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. Hydrogen bonds are drawn as dashed lines.

(E)-N'-(3-Ethoxy-4-hydroxybenzylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₇H₁₈N₂O₄	D_x = 1.347 Mg m⁻³
M_r = 314.33	Melting point = 486–488 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2637 reflections
a = 5.0607 (9) Å	θ = 1.5–30.1°
b = 11.086 (2) Å	µ = 0.10 mm⁻¹
c = 27.629 (5) Å	T = 297 K
V = 1550.1 (5) Å³	Needle, colorless
Z = 4	0.56 × 0.10 × 0.07 mm
F(000) = 664

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	2637 independent reflections
Radiation source: sealed tube	1921 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
ϕ and ω scans	θ_max = 30.1°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.948, T_max = 0.993	k = −15→15
10252 measured reflections	l = −38→29

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0865P)² + 0.0494P] where P = (F_o² + 2F_c²)/3
2637 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₄	V = 1550.1 (5) Å³
M_r = 314.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.0607 (9) Å	µ = 0.10 mm⁻¹
b = 11.086 (2) Å	T = 297 K
c = 27.629 (5) Å	0.56 × 0.10 × 0.07 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	2637 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1921 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.993	R_int = 0.100
10252 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.04	Δρ_max = 0.36 e Å⁻³
2637 reflections	Δρ_min = −0.35 e Å⁻³
210 parameters

Special details top

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	0.7066 (4)	0.1645 (2)	0.40465 (7)	0.0575 (5)
O2	0.2255 (5)	−0.16566 (19)	0.57022 (7)	0.0623 (6)
O3	0.5434 (4)	0.52128 (16)	0.19944 (6)	0.0450 (4)
O4	0.2111 (4)	0.70975 (15)	0.20065 (7)	0.0499 (5)
H1O4	0.2354	0.6755	0.1747	0.075*
N1	0.2812 (5)	0.2287 (2)	0.40261 (8)	0.0445 (5)
H1N1	0.1137	0.2022	0.4041	0.067*
N2	0.3378 (5)	0.30448 (19)	0.36411 (8)	0.0465 (5)
C1	0.4040 (5)	0.0790 (2)	0.46083 (9)	0.0390 (5)
C2	0.5413 (6)	−0.0295 (3)	0.46673 (9)	0.0469 (6)
H2A	0.6794	−0.0482	0.4458	0.056*
C3	0.4754 (7)	−0.1084 (2)	0.50282 (9)	0.0518 (7)
H3A	0.5660	−0.1810	0.5057	0.062*
C4	0.2741 (6)	−0.0809 (2)	0.53512 (9)	0.0460 (6)
C5	0.1377 (7)	0.0268 (3)	0.53087 (10)	0.0516 (7)
H5A	0.0048	0.0464	0.5527	0.062*
C6	0.2019 (6)	0.1050 (2)	0.49356 (10)	0.0471 (6)
H6A	0.1079	0.1766	0.4902	0.057*
C7	0.4803 (5)	0.1604 (2)	0.42070 (9)	0.0415 (5)
C8	0.1489 (6)	0.3765 (2)	0.35246 (9)	0.0439 (6)
H8A	−0.0064	0.3750	0.3705	0.053*
C9	0.1701 (5)	0.4600 (2)	0.31206 (9)	0.0394 (5)
C10	0.3601 (5)	0.4457 (2)	0.27571 (9)	0.0387 (5)
H10A	0.4775	0.3812	0.2770	0.046*
C11	0.3739 (5)	0.5275 (2)	0.23787 (8)	0.0363 (5)
C12	0.2013 (5)	0.6265 (2)	0.23665 (9)	0.0374 (5)
C13	0.0117 (6)	0.6400 (2)	0.27242 (9)	0.0438 (6)
H13A	−0.1046	0.7049	0.2714	0.053*
C14	−0.0044 (6)	0.5566 (2)	0.30982 (9)	0.0455 (6)
H14A	−0.1331	0.5656	0.3336	0.055*
C15	−0.0056 (8)	−0.1503 (4)	0.59944 (11)	0.0733 (10)
H15A	−0.0236	−0.2179	0.6209	0.110*
H15B	−0.1585	−0.1453	0.5790	0.110*
H15C	0.0102	−0.0776	0.6180	0.110*
C16	0.7123 (5)	0.4166 (2)	0.19693 (9)	0.0417 (5)
H16A	0.6065	0.3437	0.1961	0.050*
H16B	0.8265	0.4133	0.2251	0.050*
C17	0.8749 (7)	0.4267 (3)	0.15168 (9)	0.0539 (7)
H17A	0.9934	0.3593	0.1496	0.081*
H17B	0.9749	0.5003	0.1525	0.081*
H17C	0.7603	0.4270	0.1240	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0414 (11)	0.0677 (13)	0.0635 (12)	0.0013 (10)	0.0107 (10)	0.0136 (11)
O2	0.0805 (16)	0.0535 (11)	0.0528 (10)	−0.0074 (11)	0.0050 (12)	0.0097 (10)
O3	0.0437 (10)	0.0448 (9)	0.0465 (9)	0.0102 (8)	0.0082 (9)	0.0071 (8)
O4	0.0578 (12)	0.0402 (8)	0.0519 (10)	0.0089 (8)	0.0092 (10)	0.0100 (8)
N1	0.0411 (12)	0.0485 (11)	0.0439 (11)	−0.0042 (9)	0.0058 (10)	0.0092 (9)
N2	0.0441 (13)	0.0508 (11)	0.0445 (11)	−0.0076 (10)	0.0024 (11)	0.0059 (10)
C1	0.0379 (13)	0.0411 (11)	0.0380 (12)	−0.0011 (10)	−0.0006 (10)	−0.0033 (9)
C2	0.0437 (15)	0.0510 (13)	0.0461 (13)	0.0085 (11)	0.0032 (12)	−0.0063 (12)
C3	0.0602 (18)	0.0456 (13)	0.0496 (15)	0.0083 (13)	−0.0036 (14)	0.0001 (12)
C4	0.0525 (16)	0.0438 (12)	0.0416 (12)	−0.0070 (12)	−0.0032 (12)	−0.0025 (11)
C5	0.0522 (17)	0.0563 (14)	0.0462 (14)	0.0015 (13)	0.0104 (13)	0.0041 (12)
C6	0.0467 (14)	0.0447 (12)	0.0500 (14)	0.0076 (11)	0.0051 (13)	−0.0009 (11)
C7	0.0383 (13)	0.0431 (11)	0.0431 (12)	−0.0021 (10)	0.0031 (12)	−0.0028 (10)
C8	0.0413 (14)	0.0457 (12)	0.0448 (13)	−0.0052 (11)	0.0028 (11)	0.0008 (10)
C9	0.0387 (13)	0.0383 (10)	0.0411 (12)	−0.0036 (9)	−0.0027 (11)	0.0007 (10)
C10	0.0353 (13)	0.0359 (10)	0.0448 (12)	0.0015 (9)	−0.0023 (10)	0.0017 (9)
C11	0.0321 (11)	0.0354 (10)	0.0415 (11)	−0.0018 (9)	0.0004 (10)	−0.0005 (9)
C12	0.0350 (12)	0.0314 (9)	0.0457 (12)	0.0003 (9)	−0.0014 (11)	0.0010 (9)
C13	0.0419 (14)	0.0344 (11)	0.0549 (14)	0.0030 (10)	0.0051 (13)	−0.0016 (10)
C14	0.0430 (14)	0.0454 (12)	0.0480 (13)	−0.0020 (11)	0.0075 (12)	−0.0017 (11)
C15	0.069 (2)	0.099 (3)	0.0512 (16)	−0.021 (2)	0.0028 (18)	0.0182 (18)
C16	0.0397 (13)	0.0379 (11)	0.0474 (13)	0.0053 (10)	0.0016 (12)	0.0000 (10)
C17	0.0583 (18)	0.0576 (15)	0.0460 (14)	0.0112 (14)	0.0044 (14)	−0.0024 (12)

Geometric parameters (Å, º) top

O1—C7	1.229 (3)	C6—H6A	0.9300
O2—C4	1.373 (3)	C8—C9	1.455 (3)
O2—C15	1.431 (5)	C8—H8A	0.9300
O3—C11	1.366 (3)	C9—C14	1.390 (4)
O3—C16	1.443 (3)	C9—C10	1.400 (4)
O4—C12	1.358 (3)	C10—C11	1.385 (3)
O4—H1O4	0.8198	C10—H10A	0.9300
N1—C7	1.356 (4)	C11—C12	1.403 (3)
N1—N2	1.386 (3)	C12—C13	1.386 (4)
N1—H1N1	0.8977	C13—C14	1.389 (3)
N2—C8	1.286 (4)	C13—H13A	0.9300
C1—C6	1.396 (4)	C14—H14A	0.9300
C1—C2	1.398 (4)	C15—H15A	0.9600
C1—C7	1.481 (3)	C15—H15B	0.9600
C2—C3	1.368 (4)	C15—H15C	0.9600
C2—H2A	0.9300	C16—C17	1.501 (4)
C3—C4	1.388 (4)	C16—H16A	0.9700
C3—H3A	0.9300	C16—H16B	0.9700
C4—C5	1.384 (4)	C17—H17A	0.9600
C5—C6	1.385 (4)	C17—H17B	0.9600
C5—H5A	0.9300	C17—H17C	0.9600

C4—O2—C15	117.6 (3)	C11—C10—C9	120.1 (2)
C11—O3—C16	116.72 (18)	C11—C10—H10A	119.9
C12—O4—H1O4	109.3	C9—C10—H10A	119.9
C7—N1—N2	117.9 (2)	O3—C11—C10	125.8 (2)
C7—N1—H1N1	120.2	O3—C11—C12	114.3 (2)
N2—N1—H1N1	115.3	C10—C11—C12	119.9 (2)
C8—N2—N1	114.5 (2)	O4—C12—C13	118.3 (2)
C6—C1—C2	117.8 (2)	O4—C12—C11	121.8 (2)
C6—C1—C7	123.4 (2)	C13—C12—C11	119.9 (2)
C2—C1—C7	118.8 (2)	C12—C13—C14	119.9 (2)
C3—C2—C1	120.9 (3)	C12—C13—H13A	120.0
C3—C2—H2A	119.5	C14—C13—H13A	120.0
C1—C2—H2A	119.5	C13—C14—C9	120.6 (2)
C2—C3—C4	120.5 (3)	C13—C14—H14A	119.7
C2—C3—H3A	119.8	C9—C14—H14A	119.7
C4—C3—H3A	119.8	O2—C15—H15A	109.5
O2—C4—C5	124.2 (3)	O2—C15—H15B	109.5
O2—C4—C3	115.8 (3)	H15A—C15—H15B	109.5
C5—C4—C3	120.1 (3)	O2—C15—H15C	109.5
C4—C5—C6	119.1 (3)	H15A—C15—H15C	109.5
C4—C5—H5A	120.5	H15B—C15—H15C	109.5
C6—C5—H5A	120.5	O3—C16—C17	107.8 (2)
C5—C6—C1	121.7 (3)	O3—C16—H16A	110.2
C5—C6—H6A	119.2	C17—C16—H16A	110.2
C1—C6—H6A	119.2	O3—C16—H16B	110.2
O1—C7—N1	122.6 (2)	C17—C16—H16B	110.2
O1—C7—C1	122.4 (3)	H16A—C16—H16B	108.5
N1—C7—C1	115.0 (2)	C16—C17—H17A	109.5
N2—C8—C9	122.2 (2)	C16—C17—H17B	109.5
N2—C8—H8A	118.9	H17A—C17—H17B	109.5
C9—C8—H8A	118.9	C16—C17—H17C	109.5
C14—C9—C10	119.5 (2)	H17A—C17—H17C	109.5
C14—C9—C8	118.6 (2)	H17B—C17—H17C	109.5
C10—C9—C8	122.0 (2)

C7—N1—N2—C8	−172.3 (2)	N1—N2—C8—C9	−178.2 (2)
C6—C1—C2—C3	1.4 (4)	N2—C8—C9—C14	−162.0 (3)
C7—C1—C2—C3	−179.0 (3)	N2—C8—C9—C10	18.0 (4)
C1—C2—C3—C4	−1.6 (4)	C14—C9—C10—C11	0.1 (4)
C15—O2—C4—C5	10.0 (4)	C8—C9—C10—C11	−179.9 (2)
C15—O2—C4—C3	−170.4 (3)	C16—O3—C11—C10	3.6 (3)
C2—C3—C4—O2	−179.4 (3)	C16—O3—C11—C12	−175.6 (2)
C2—C3—C4—C5	0.3 (4)	C9—C10—C11—O3	−177.6 (2)
O2—C4—C5—C6	−179.2 (3)	C9—C10—C11—C12	1.6 (4)
C3—C4—C5—C6	1.2 (4)	O3—C11—C12—O4	−1.8 (3)
C4—C5—C6—C1	−1.3 (4)	C10—C11—C12—O4	178.9 (2)
C2—C1—C6—C5	0.1 (4)	O3—C11—C12—C13	177.1 (2)
C7—C1—C6—C5	−179.5 (3)	C10—C11—C12—C13	−2.2 (4)
N2—N1—C7—O1	0.8 (4)	O4—C12—C13—C14	180.0 (2)
N2—N1—C7—C1	−178.3 (2)	C11—C12—C13—C14	1.0 (4)
C6—C1—C7—O1	150.6 (3)	C12—C13—C14—C9	0.7 (4)
C2—C1—C7—O1	−29.0 (4)	C10—C9—C14—C13	−1.2 (4)
C6—C1—C7—N1	−30.2 (4)	C8—C9—C14—C13	178.8 (2)
C2—C1—C7—N1	150.2 (2)	C11—O3—C16—C17	178.5 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O3	0.82	2.41	2.683 (2)	100
O4—H1O4···O1ⁱ	0.82	2.21	2.981 (2)	156
N1—H1N1···O1ⁱⁱ	0.90	2.10	2.994 (3)	172
C10—H10A···O4ⁱⁱⁱ	0.93	2.55	3.462 (3)	168
C16—H16B···Cg1ⁱ	0.97	2.68	3.499 (2)	142

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₄
M_r	314.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	297
a, b, c (Å)	5.0607 (9), 11.086 (2), 27.629 (5)
V (Å³)	1550.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.56 × 0.10 × 0.07

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.948, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	10252, 2637, 1921
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.154, 1.04
No. of reflections	2637
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

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 C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O3	0.82	2.41	2.683 (2)	100
O4—H1O4···O1ⁱ	0.82	2.21	2.981 (2)	156
N1—H1N1···O1ⁱⁱ	0.90	2.10	2.994 (3)	172
C10—H10A···O4ⁱⁱⁱ	0.93	2.55	3.462 (3)	168
C16—H16B···Cg1ⁱ	0.97	2.68	3.499 (2)	142

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

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

Acknowledgements

PP thanks the Development and Promotion of Science and Technology Talents Project for a fellowship. JH thanks the Crystal Materials Research Unit, Prince of Songkla University, for financial support. PP and JH thank Dr Nawong Boonnak for useful suggestions. Mr Teerasak Anantapong, Department of Biotechnology, Faculty of Agro-Industry, Prince of Songkla University, is acknowledged for baterial assays. The authors thank the Prince of Songkla University and the Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.

References

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Volume 68| Part 3| March 2012| Pages o849-o850

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