(E)-4-Hy­droxy-N′-(3,4,5-trimeth­oxy­benzyl­idene)benzohydrazide

Horkaew, J.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536811041535

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2985

doi:10.1107/S1600536811041535

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(E)-4-Hydroxy-N′-(3,4,5-trimethoxybenzylidene)benzohydrazide

Jirapa Horkaew,^a Suchada Chantrapromma ^b ^*‡ and Hoong-Kun Fun ^c §

^aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, ^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: suchada.c@psu.ac.th

(Received 8 October 2011; accepted 9 October 2011; online 22 October 2011)

The title benzohydrazide derivative, C₁₇H₁₈N₂O₅, exists in a trans conformation with respect to the C=N double bond. The dihedral angle between the benzene rings is 19.41 (5)°. The two methoxy groups at the meta positions of the trimethoxybenzene group are almost coplanar with the ring [C—O—C—C = 1.62 (16) and 178.33 (10)°], whereas the third methoxy group, at the para position, is (+)-synclinal with the ring. In the crystal, molecules are linked by N—H⋯O and bifurcated O—H⋯(N,O) hydrogen bonds, as well as weak C—H⋯O interactions, into sheets lying parallel to the ac plane. A C—H⋯π interaction also occurs.

Related literature

For a related structure and background references to benzohydrazide derivatives, see: Fun et al. (2011 ). For related structures, see: Li & Ban (2009 ); Zhang (2011 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₅
M_r = 330.33
Orthorhombic, P b c a
a = 14.4623 (8) Å
b = 10.9202 (6) Å
c = 19.5592 (10) Å
V = 3089.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 297 K
0.39 × 0.21 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.960, T_max = 0.979
20210 measured reflections
4500 independent reflections
3777 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.03
4500 reflections
228 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1ⁱ	0.87 (2)	1.87 (2)	2.6646 (11)	152 (2)
O2—H1O2⋯N2ⁱ	0.87 (2)	2.56 (2)	3.2381 (13)	136.2 (18)
N1—H1N1⋯O4ⁱⁱ	0.874 (17)	2.088 (17)	2.8891 (12)	152.0 (16)
C6—H6A⋯O4ⁱⁱ	0.93	2.51	3.4116 (14)	165
C16—H16B⋯Cg1ⁱⁱⁱ	0.96	2.63	3.4572 (17)	145
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ ; (iii) -x, -y+2, -z+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/S1600536811041535/hb6444sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041535/hb6444Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041535/hb6444Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of benzohydrazide derivatives with possible antibacterial activities (Fun et al., 2011), we now report the synthesis and structure of the title compound, (I). The antibacterial activity of (I) will be reported elsewhere with other related benzohydrazide derivatives.

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₇H₁₈N₂O₅, exists in a trans-configuration with respect to the C8═N2 bond [1.2821 (15) Å] and the torsion angle N1–N2–C8–C9 = 178.33 (10)°. The molecule is twisted with the dihedral angle between the two benzene rings being 19.41 (5)°. The middle fragment is slightly twisted which can be indicated by the torsion angle O1–C7–N1–N2 = -6.63 (15)°. The mean plane through this middle bridge (O1/C7/N1/N2/C8) makes the dihedral angles of 12.06 (6) and 8.39 (6)° with the planes of 4-hydroxyphenyl and 3,4,5-trimethoxyphenyl rings, respectively. The three methoxy groups of the 3,4,5-trimethoxyphenyl unit have two different orientations: the two meta methoxy groups (at atoms C11 and C13 positions) are co-planar with their attached benzene ring with torsion angles C15–O3–C11–C10 = 1.62 (16)° and C17–O5–C13–C12 = 178.33 (10)° whereas the para methoxy is (+)-syn-clinally attached at atom C12 with the torsion angle C16–O4–C12–C11 = 71.28 (15)°. Bond distances are of normal values (Allen et al., 1987) and are comparable with the related structures (Fun et al., 2011; Li & Ban, 2009; Zhang, 2011).

In the crystal packing (Fig. 2), the molecules are linked by N—H···O, O—H···N and O—H···O hydrogen bonds as well as with weak C—H···O interactions (Table 1) into sheets parallel to the ac plane. The crystal structure is stabilized by N—H···O, O—H···N, O—H···O hydrogen bonds, weak C—H···O and C—H···π interactions (Table 1).

Related literature top

For a related structure and background references to benzohydrazide derivatives, see: Fun et al. (2011). For related structures, see: Li & Ban (2009); Zhang (2011). For reference bond-length data, see: Allen et al. (1987).

Experimental top

The title compound (I) was prepared by dissolving 4-hydroxybenzohydrazide (0.1 mmol, 0.15 g) in ethanol (15 ml) and a solution of 3,4,5-trimethoxybenzaldehyde (0.1 mmol, 0.19 g) in ethanol (15 ml) was then added to it0. The mixture was refluxed for around 3 hr and the white solid of the product that appeared was collected by filtration, washed with ethanol and dried in air. Colorless blocks of (I) were obtained after recrystalization from methanol by slow evaporation of the solvent at room temperature after several days, Mp. 532-533 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 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewed along the b axis, Hydrogen bonds were shown as dashed lines.

(E)-4-Hydroxy-N'-(3,4,5-trimethoxybenzylidene)benzohydrazide top

Crystal data top

C₁₇H₁₈N₂O₅	D_x = 1.421 Mg m⁻³
M_r = 330.33	Melting point = 533–532 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4500 reflections
a = 14.4623 (8) Å	θ = 2.1–30.0°
b = 10.9202 (6) Å	µ = 0.11 mm⁻¹
c = 19.5592 (10) Å	T = 297 K
V = 3089.0 (3) Å³	Block, colorless
Z = 8	0.39 × 0.21 × 0.20 mm
F(000) = 1392

Data collection top

Bruker SMART APEXII CCD diffractometer	4500 independent reflections
Radiation source: fine-focus sealed tube	3777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scans	h = −18→20
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −15→14
T_min = 0.960, T_max = 0.979	l = −27→27
20210 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0512P)² + 1.5827P] where P = (F_o² + 2F_c²)/3
4500 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₅	V = 3089.0 (3) Å³
M_r = 330.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.4623 (8) Å	µ = 0.11 mm⁻¹
b = 10.9202 (6) Å	T = 297 K
c = 19.5592 (10) Å	0.39 × 0.21 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	4500 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3777 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.979	R_int = 0.028
20210 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
4500 reflections	Δρ_min = −0.32 e Å⁻³
228 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	0.02505 (5)	1.10904 (8)	0.80535 (4)	0.01825 (17)
O2	−0.32653 (6)	1.14816 (8)	0.61694 (4)	0.01926 (18)
H1O2	−0.3790 (16)	1.119 (2)	0.6311 (11)	0.051 (6)*
O3	0.32914 (5)	0.88335 (8)	1.01826 (4)	0.01920 (18)
O4	0.29967 (5)	0.71610 (8)	1.11552 (4)	0.01747 (17)
O5	0.13085 (6)	0.63448 (8)	1.14433 (4)	0.01937 (18)
N1	−0.06135 (6)	0.96981 (9)	0.86248 (5)	0.01526 (18)
H1N1	−0.1150 (12)	0.9362 (16)	0.8709 (9)	0.029 (4)*
N2	0.01401 (6)	0.94312 (9)	0.90309 (5)	0.01538 (18)
C1	−0.12442 (7)	1.07047 (10)	0.76129 (5)	0.0147 (2)
C2	−0.11500 (7)	1.16838 (11)	0.71558 (6)	0.0165 (2)
H2A	−0.0627	1.2178	0.7178	0.020*
C3	−0.18213 (8)	1.19281 (11)	0.66718 (6)	0.0167 (2)
H3A	−0.1747	1.2578	0.6369	0.020*
C4	−0.26122 (7)	1.11954 (10)	0.66390 (5)	0.0155 (2)
C5	−0.26994 (7)	1.01888 (11)	0.70742 (6)	0.0163 (2)
H5A	−0.3212	0.9678	0.7039	0.020*
C6	−0.20211 (7)	0.99504 (10)	0.75593 (6)	0.0162 (2)
H6A	−0.2085	0.9283	0.7851	0.019*
C7	−0.04843 (7)	1.05222 (10)	0.81117 (5)	0.0142 (2)
C8	−0.00007 (7)	0.87131 (10)	0.95390 (6)	0.0155 (2)
H8A	−0.0592	0.8419	0.9630	0.019*
C9	0.07833 (7)	0.83586 (10)	0.99769 (5)	0.0144 (2)
C10	0.16646 (7)	0.88419 (10)	0.98592 (5)	0.0154 (2)
H10A	0.1756	0.9421	0.9517	0.019*
C11	0.24005 (7)	0.84492 (10)	1.02576 (5)	0.0153 (2)
C12	0.22580 (7)	0.75942 (10)	1.07816 (5)	0.0152 (2)
C13	0.13721 (7)	0.71439 (10)	1.09113 (5)	0.0153 (2)
C14	0.06307 (7)	0.75202 (10)	1.05023 (5)	0.0155 (2)
H14A	0.0040	0.7213	1.0580	0.019*
C15	0.34575 (8)	0.97270 (12)	0.96645 (6)	0.0208 (2)
H15A	0.4092	0.9982	0.9682	0.031*
H15B	0.3064	1.0422	0.9739	0.031*
H15C	0.3328	0.9379	0.9224	0.031*
C16	0.33986 (12)	0.80230 (13)	1.16153 (8)	0.0366 (4)
H16A	0.4044	0.7842	1.1672	0.055*
H16B	0.3093	0.7973	1.2050	0.055*
H16C	0.3330	0.8834	1.1433	0.055*
C17	0.04118 (8)	0.58866 (12)	1.16066 (6)	0.0221 (2)
H17A	0.0450	0.5378	1.2006	0.033*
H17B	0.0181	0.5414	1.1230	0.033*
H17C	0.0001	0.6560	1.1694	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0125 (3)	0.0233 (4)	0.0190 (4)	−0.0017 (3)	0.0000 (3)	0.0030 (3)
O2	0.0142 (4)	0.0264 (4)	0.0172 (4)	−0.0013 (3)	−0.0031 (3)	0.0046 (3)
O3	0.0124 (4)	0.0266 (4)	0.0186 (4)	−0.0017 (3)	−0.0006 (3)	0.0051 (3)
O4	0.0140 (3)	0.0186 (4)	0.0197 (4)	0.0021 (3)	−0.0051 (3)	0.0012 (3)
O5	0.0163 (4)	0.0222 (4)	0.0197 (4)	−0.0015 (3)	−0.0027 (3)	0.0078 (3)
N1	0.0108 (4)	0.0191 (4)	0.0158 (4)	−0.0002 (3)	−0.0020 (3)	0.0032 (3)
N2	0.0124 (4)	0.0185 (4)	0.0152 (4)	0.0024 (3)	−0.0027 (3)	−0.0001 (3)
C1	0.0121 (4)	0.0184 (5)	0.0135 (4)	0.0012 (4)	0.0003 (3)	0.0009 (4)
C2	0.0139 (5)	0.0193 (5)	0.0164 (5)	−0.0026 (4)	0.0002 (4)	0.0015 (4)
C3	0.0164 (5)	0.0187 (5)	0.0150 (5)	−0.0016 (4)	0.0001 (4)	0.0033 (4)
C4	0.0134 (4)	0.0197 (5)	0.0134 (4)	0.0016 (4)	0.0004 (4)	0.0000 (4)
C5	0.0132 (4)	0.0180 (5)	0.0176 (5)	−0.0014 (4)	−0.0002 (4)	0.0012 (4)
C6	0.0147 (5)	0.0170 (5)	0.0167 (5)	0.0003 (4)	0.0003 (4)	0.0031 (4)
C7	0.0124 (4)	0.0167 (5)	0.0134 (4)	0.0021 (4)	0.0011 (3)	−0.0001 (4)
C8	0.0132 (4)	0.0177 (5)	0.0157 (5)	0.0007 (4)	−0.0011 (4)	−0.0008 (4)
C9	0.0135 (4)	0.0157 (5)	0.0138 (4)	0.0017 (4)	−0.0009 (3)	−0.0015 (4)
C10	0.0142 (5)	0.0182 (5)	0.0139 (4)	0.0002 (4)	0.0003 (4)	0.0008 (4)
C11	0.0124 (4)	0.0184 (5)	0.0152 (4)	0.0002 (4)	0.0008 (4)	−0.0010 (4)
C12	0.0132 (4)	0.0173 (5)	0.0151 (4)	0.0028 (4)	−0.0016 (3)	0.0001 (4)
C13	0.0160 (5)	0.0163 (5)	0.0136 (4)	0.0010 (4)	−0.0010 (4)	0.0005 (4)
C14	0.0132 (4)	0.0172 (5)	0.0160 (5)	0.0000 (4)	−0.0006 (4)	0.0002 (4)
C15	0.0168 (5)	0.0258 (6)	0.0199 (5)	−0.0023 (4)	0.0012 (4)	0.0046 (4)
C16	0.0504 (9)	0.0268 (7)	0.0326 (7)	0.0135 (6)	−0.0256 (7)	−0.0118 (6)
C17	0.0182 (5)	0.0249 (6)	0.0233 (6)	−0.0036 (4)	−0.0010 (4)	0.0079 (5)

Geometric parameters (Å, º) top

O1—C7	1.2358 (13)	C5—H5A	0.9300
O2—C4	1.3542 (13)	C6—H6A	0.9300
O2—H1O2	0.87 (2)	C8—C9	1.4727 (14)
O3—C11	1.3630 (13)	C8—H8A	0.9300
O3—C15	1.4270 (14)	C9—C14	1.3939 (15)
O4—C12	1.3780 (12)	C9—C10	1.3986 (15)
O4—C16	1.4262 (15)	C10—C11	1.3871 (15)
O5—C13	1.3611 (13)	C10—H10A	0.9300
O5—C17	1.4262 (14)	C11—C12	1.4016 (15)
N1—C7	1.3608 (14)	C12—C13	1.3957 (15)
N1—N2	1.3797 (12)	C13—C14	1.3995 (15)
N1—H1N1	0.874 (18)	C14—H14A	0.9300
N2—C8	1.2821 (15)	C15—H15A	0.9600
C1—C6	1.3971 (15)	C15—H15B	0.9600
C1—C2	1.4004 (15)	C15—H15C	0.9600
C1—C7	1.4831 (14)	C16—H16A	0.9600
C2—C3	1.3820 (15)	C16—H16B	0.9600
C2—H2A	0.9300	C16—H16C	0.9600
C3—C4	1.3974 (15)	C17—H17A	0.9600
C3—H3A	0.9300	C17—H17B	0.9600
C4—C5	1.3959 (15)	C17—H17C	0.9600
C5—C6	1.3894 (15)

C4—O2—H1O2	108.0 (14)	C10—C9—C8	120.44 (10)
C11—O3—C15	116.49 (9)	C11—C10—C9	119.34 (10)
C12—O4—C16	115.09 (9)	C11—C10—H10A	120.3
C13—O5—C17	117.23 (9)	C9—C10—H10A	120.3
C7—N1—N2	117.12 (9)	O3—C11—C10	124.72 (10)
C7—N1—H1N1	122.6 (11)	O3—C11—C12	115.01 (9)
N2—N1—H1N1	120.2 (11)	C10—C11—C12	120.26 (10)
C8—N2—N1	116.75 (9)	O4—C12—C13	119.62 (10)
C6—C1—C2	118.72 (10)	O4—C12—C11	120.16 (9)
C6—C1—C7	124.48 (10)	C13—C12—C11	120.17 (10)
C2—C1—C7	116.77 (10)	O5—C13—C12	115.27 (9)
C3—C2—C1	121.09 (10)	O5—C13—C14	125.00 (10)
C3—C2—H2A	119.5	C12—C13—C14	119.73 (10)
C1—C2—H2A	119.5	C9—C14—C13	119.54 (10)
C2—C3—C4	119.73 (10)	C9—C14—H14A	120.2
C2—C3—H3A	120.1	C13—C14—H14A	120.2
C4—C3—H3A	120.1	O3—C15—H15A	109.5
O2—C4—C5	122.16 (10)	O3—C15—H15B	109.5
O2—C4—C3	118.03 (10)	H15A—C15—H15B	109.5
C5—C4—C3	119.79 (10)	O3—C15—H15C	109.5
C6—C5—C4	120.01 (10)	H15A—C15—H15C	109.5
C6—C5—H5A	120.0	H15B—C15—H15C	109.5
C4—C5—H5A	120.0	O4—C16—H16A	109.5
C5—C6—C1	120.57 (10)	O4—C16—H16B	109.5
C5—C6—H6A	119.7	H16A—C16—H16B	109.5
C1—C6—H6A	119.7	O4—C16—H16C	109.5
O1—C7—N1	121.20 (10)	H16A—C16—H16C	109.5
O1—C7—C1	120.61 (10)	H16B—C16—H16C	109.5
N1—C7—C1	118.18 (9)	O5—C17—H17A	109.5
N2—C8—C9	119.29 (10)	O5—C17—H17B	109.5
N2—C8—H8A	120.4	H17A—C17—H17B	109.5
C9—C8—H8A	120.4	O5—C17—H17C	109.5
C14—C9—C10	120.90 (10)	H17A—C17—H17C	109.5
C14—C9—C8	118.65 (10)	H17B—C17—H17C	109.5

C7—N1—N2—C8	175.78 (10)	C8—C9—C10—C11	−176.91 (10)
C6—C1—C2—C3	1.83 (17)	C15—O3—C11—C10	1.62 (16)
C7—C1—C2—C3	179.98 (10)	C15—O3—C11—C12	−178.52 (10)
C1—C2—C3—C4	0.52 (17)	C9—C10—C11—O3	178.62 (10)
C2—C3—C4—O2	178.38 (10)	C9—C10—C11—C12	−1.23 (16)
C2—C3—C4—C5	−2.91 (17)	C16—O4—C12—C13	−111.02 (14)
O2—C4—C5—C6	−178.41 (10)	C16—O4—C12—C11	71.28 (15)
C3—C4—C5—C6	2.94 (16)	O3—C11—C12—O4	−2.99 (15)
C4—C5—C6—C1	−0.57 (17)	C10—C11—C12—O4	176.88 (10)
C2—C1—C6—C5	−1.80 (16)	O3—C11—C12—C13	179.33 (10)
C7—C1—C6—C5	−179.80 (10)	C10—C11—C12—C13	−0.80 (17)
N2—N1—C7—O1	−6.63 (15)	C17—O5—C13—C12	178.33 (10)
N2—N1—C7—C1	172.15 (9)	C17—O5—C13—C14	−1.93 (16)
C6—C1—C7—O1	167.40 (11)	O4—C12—C13—O5	4.06 (15)
C2—C1—C7—O1	−10.63 (15)	C11—C12—C13—O5	−178.24 (10)
C6—C1—C7—N1	−11.39 (16)	O4—C12—C13—C14	−175.69 (10)
C2—C1—C7—N1	170.58 (10)	C11—C12—C13—C14	2.00 (16)
N1—N2—C8—C9	177.83 (9)	C10—C9—C14—C13	−0.90 (16)
N2—C8—C9—C14	−176.20 (10)	C8—C9—C14—C13	178.12 (10)
N2—C8—C9—C10	2.83 (16)	O5—C13—C14—C9	179.12 (10)
C14—C9—C10—C11	2.10 (16)	C12—C13—C14—C9	−1.15 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1ⁱ	0.87 (2)	1.87 (2)	2.6646 (11)	152 (2)
O2—H1O2···N2ⁱ	0.87 (2)	2.56 (2)	3.2381 (13)	136.2 (18)
N1—H1N1···O4ⁱⁱ	0.874 (17)	2.088 (17)	2.8891 (12)	152.0 (16)
C6—H6A···O4ⁱⁱ	0.93	2.51	3.4116 (14)	165
C16—H16B···Cg1ⁱⁱⁱ	0.96	2.63	3.4572 (17)	145

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x−1/2, −y+3/2, −z+2; (iii) −x, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₅
M_r	330.33
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	297
a, b, c (Å)	14.4623 (8), 10.9202 (6), 19.5592 (10)
V (Å³)	3089.0 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.39 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.960, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	20210, 4500, 3777
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.03
No. of reflections	4500
No. of parameters	228
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.32

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 C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1ⁱ	0.87 (2)	1.87 (2)	2.6646 (11)	152 (2)
O2—H1O2···N2ⁱ	0.87 (2)	2.56 (2)	3.2381 (13)	136.2 (18)
N1—H1N1···O4ⁱⁱ	0.874 (17)	2.088 (17)	2.8891 (12)	152.0 (16)
C6—H6A···O4ⁱⁱ	0.93	2.51	3.4116 (14)	165
C16—H16B···Cg1ⁱⁱⁱ	0.96	2.63	3.4572 (17)	145

Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x−1/2, −y+3/2, −z+2; (iii) −x, −y+2, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§Thomson Reuters ResearcherID: A-3561-2009. Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

JH thanks the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commission on Higher Education, Ministry of Education, and the Graduate School, Prince of Songkla University, for financial support. The authors thank the Prince of Songkla University through the Crystal Materials Research Unit and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Horkaew, J. & Chantrapromma, S. (2011). Acta Cryst. E67, o2644–o2645. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Li, C.-M. & Ban, H.-Y. (2009). Acta Cryst. E65, o876. Web of Science CSD CrossRef 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. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z. (2011). Acta Cryst. E67, o300. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o2985

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