(E)-N′-(3-Hy­droxy-4-meth­oxy­benzyl­idene)-4-meth­oxy­benzohydrazide

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

doi:10.1107/S1600536811048240

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages o3370-o3371

https://doi.org/10.1107/S1600536811048240

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(E)-N′-(3-Hydroxy-4-methoxybenzylidene)-4-methoxybenzohydrazide

Hoong-Kun Fun,^a ^*‡ Premrudee Promdet,^b Suchada Chantrapromma,^b § Jirapa Horkaew ^b and Chatchanok Karalai ^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 11 November 2011; accepted 14 November 2011; online 19 November 2011)

The title molecule, a benzohydrazide derivative, C₁₆H₁₆N₂O₄, is twisted with a dihedral angle of 69.97 (5)° between the two benzene rings. An intramolecular O—H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, molecules are linked by N—H⋯O and weak C—H⋯O hydrogen bonds into a chain along the c axis. C—H⋯π interactions are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ). For details of 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 of benzohydrazide derivatives, see: Bedia et al. (2006 ); Loncle et al. (2004 ); Melnyk et al. (2006 ); Raj et al. (2007 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₄
M_r = 300.31
Monoclinic, P 2₁ /c
a = 12.1323 (19) Å
b = 12.9727 (15) Å
c = 9.6714 (12) Å
β = 113.213 (2)°
V = 1398.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 K
0.58 × 0.30 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.942, T_max = 0.993
14521 measured reflections
3704 independent reflections
3260 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.109
S = 1.03
3704 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.23 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
O3—H1O3⋯O4	0.87 (2)	2.18 (2)	2.6692 (13)	115.9 (18)
N1—H1N1⋯O1ⁱ	0.887 (18)	1.992 (18)	2.8698 (13)	170.0 (16)
C8—H8A⋯O1ⁱ	0.93	2.47	3.2780 (15)	145
C15—H15C⋯Cg1ⁱⁱ	0.96	2.72	3.5664 (15)	148
C16—H16B⋯Cg1ⁱⁱⁱ	0.96	2.76	3.4366 (16)	128
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z; (iii) x, y-1, 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: https://doi.org/10.1107/S1600536811048240/is5009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048240/is5009Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811048240/is5009Isup3.cml

checkCIF report

Comment top

Benzohydrazide derivatives have been reported to possess various biological properties, such as antibacterial and antifungal (Loncle et al., 2004), antitubercular (Bedia et al., 2006), antimalarial (Melnyk et al., 2006) and antiproliferative (Raj et al., 2007) activities. We have previously reported some crystal structures of this type of compounds (Fun et al., 2011; Horkaew et al., 2011; Promdet et al., 2011). The title compound (I) was synthesized in order to study the effect of functional groups to their bioactivities comparing to the closely related structures. (I) was screened for antibacterial and antioxidant activities. Our results show that (I) exhibits moderate antibacterial activity whereas it is inactive for antioxidant activity. The three dimensional structure of (I) was studied in order to gain more details to explain the effect of structure on its bioactivity.

The molecule of the title benzohydrazide derivative (Fig. 1), C₁₆H₁₆N₂O₄, exists in a trans-configuration with respect to the C8═N2 bond [1.2808 (14) Å] and the torsion angle of N1–N2–C8–C9 is 179.20 (9)°. The molecule is twisted as indicated by the dihedral angle between the two benzene rings being 69.97 (5)°. The middle bridge fragment (O1/C7/N1/N2/C8) is nearly planar with a torsion angle N2–N1–C7–O1 = -0.80 (16)°. The mean plane through this bridge makes dihedral angles of 27.88 (7) and 43.44 (7)° with the C1–C6 and C9–C14 benzene rings, respectively. The methoxy group of 4-methoxyphenyl (at atom C4) is co-planar with its bound benzene ring [torsion angle C15–O2–C4–C5 = -0.76 (16)° and r.m.s 0.0131 (1) Å for the seven non H atoms], whereas the methoxy group of the 3-hydroxy-4-methoxyphenyl (at atom C12) is slight deviated with a torsion angle C16–O4–C12–C13 = 10.02 (15)°. An intramolecular O3—H1O3···O4 hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995). Bond distances are of normal values (Allen et al., 1987) and are comparable with the 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 hydrogen bonds and weak C—H···O interactions (Table 1) into chains along the c axis. These chains are arranged in a face-to-face manner. The crystal is stabilized by N—H···O hydrogen bonds, weak C—H···O and C—H···π interactions (Table 1).

Related literature top

For bond-length data, see: Allen et al. (1987). For details of 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 of benzohydrazide derivatives, see: Bedia et al. (2006); Loncle et al. (2004); Melnyk et al. (2006); Raj et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound (I) was prepared by dissolving 4-methoxybenzohydrazide (2 mmol, 0.33 g) in ethanol (10 ml). The solution of 3-hydroxy-4-methoxybenzaldehyde (2 mmol, 0.30 g) in ethanol (10 ml) was then added slowly to the reaction. The mixture was refluxed for around 3 hr. The solution was then cooled to room temperature. Colorless plate-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. 491-492 K).

Structure description top

For bond-length data, see: Allen et al. (1987). For details of 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 of benzohydrazide derivatives, see: Bedia et al. (2006); Loncle et al. (2004); Melnyk et al. (2006); Raj et al. (2007). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

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 60% probability displacement ellipsoids and the atom-numbering scheme. Hydrogen bond was drawn as a dash line.
	Fig. 2. A crystal packing diagram of the title compound viewed along the b axis, showing chains running along the c axis. Hydrogen bonds were drawn as dashed lines.

(E)-N'-(3-Hydroxy-4-methoxybenzylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₆H₁₆N₂O₄	F(000) = 632
M_r = 300.31	D_x = 1.426 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 491–492 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.1323 (19) Å	Cell parameters from 3704 reflections
b = 12.9727 (15) Å	θ = 1.8–29.0°
c = 9.6714 (12) Å	µ = 0.10 mm⁻¹
β = 113.213 (2)°	T = 100 K
V = 1398.9 (3) Å³	Plate, colorless
Z = 4	0.58 × 0.30 × 0.07 mm

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3704 independent reflections
Radiation source: sealed tube	3260 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 29.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→16
T_min = 0.942, T_max = 0.993	k = −17→16
14521 measured reflections	l = −13→13

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)] = 0.037	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) + (0.058P)² + 0.5751P] where P = (F_o² + 2F_c²)/3
3704 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₄	V = 1398.9 (3) Å³
M_r = 300.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1323 (19) Å	µ = 0.10 mm⁻¹
b = 12.9727 (15) Å	T = 100 K
c = 9.6714 (12) Å	0.58 × 0.30 × 0.07 mm
β = 113.213 (2)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	3704 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3260 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.993	R_int = 0.021
14521 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.39 e Å⁻³
3704 reflections	Δρ_min = −0.23 e Å⁻³
208 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	0.29470 (7)	0.79595 (6)	0.37018 (8)	0.01765 (17)
O2	0.47609 (8)	1.16425 (6)	0.09037 (9)	0.02033 (18)
O3	−0.02649 (8)	0.33066 (7)	0.26553 (10)	0.02208 (19)
H1O3	−0.0427 (18)	0.2655 (17)	0.262 (2)	0.049 (6)*
O4	0.05699 (8)	0.16672 (6)	0.17060 (10)	0.02052 (18)
N1	0.24563 (9)	0.72966 (7)	0.13517 (10)	0.01662 (19)
H1N1	0.2597 (15)	0.7299 (13)	0.0519 (19)	0.027 (4)*
N2	0.20136 (8)	0.63908 (7)	0.16926 (10)	0.01754 (19)
C1	0.33802 (9)	0.89609 (8)	0.19231 (11)	0.0143 (2)
C2	0.42433 (10)	0.95553 (8)	0.30308 (11)	0.0169 (2)
H2A	0.4511	0.9355	0.4033	0.020*
C3	0.47027 (10)	1.04352 (8)	0.26570 (11)	0.0175 (2)
H3A	0.5285	1.0818	0.3403	0.021*
C4	0.42906 (9)	1.07495 (8)	0.11550 (12)	0.0158 (2)
C5	0.34465 (9)	1.01566 (8)	0.00388 (11)	0.0162 (2)
H5A	0.3184	1.0355	−0.0964	0.019*
C6	0.29974 (9)	0.92674 (8)	0.04258 (11)	0.0155 (2)
H6A	0.2434	0.8872	−0.0323	0.019*
C7	0.29096 (9)	0.80337 (8)	0.24151 (11)	0.0143 (2)
C8	0.20399 (10)	0.56293 (9)	0.08631 (12)	0.0174 (2)
H8A	0.2331	0.5735	0.0117	0.021*
C9	0.16289 (9)	0.46024 (8)	0.10510 (11)	0.0167 (2)
C10	0.08516 (9)	0.44367 (8)	0.17847 (11)	0.0170 (2)
H10A	0.0565	0.4994	0.2150	0.020*
C11	0.05118 (9)	0.34488 (8)	0.19644 (12)	0.0168 (2)
C12	0.09594 (9)	0.26028 (8)	0.14405 (12)	0.0167 (2)
C13	0.17260 (10)	0.27633 (9)	0.07125 (12)	0.0192 (2)
H13A	0.2022	0.2205	0.0362	0.023*
C14	0.20503 (10)	0.37620 (9)	0.05082 (12)	0.0192 (2)
H14A	0.2554	0.3869	0.0004	0.023*
C15	0.43662 (11)	1.19826 (9)	−0.06160 (13)	0.0221 (2)
H15A	0.4779	1.2606	−0.0655	0.033*
H15B	0.3518	1.2110	−0.1008	0.033*
H15C	0.4535	1.1461	−0.1208	0.033*
C16	0.11532 (11)	0.07892 (9)	0.14054 (14)	0.0228 (2)
H16A	0.0817	0.0171	0.1624	0.034*
H16B	0.1995	0.0817	0.2025	0.034*
H16C	0.1039	0.0790	0.0365	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0231 (4)	0.0179 (4)	0.0150 (3)	0.0017 (3)	0.0108 (3)	0.0010 (3)
O2	0.0243 (4)	0.0178 (4)	0.0183 (4)	−0.0057 (3)	0.0077 (3)	0.0011 (3)
O3	0.0220 (4)	0.0190 (4)	0.0318 (4)	−0.0008 (3)	0.0175 (3)	0.0007 (3)
O4	0.0227 (4)	0.0151 (4)	0.0284 (4)	−0.0019 (3)	0.0150 (3)	0.0001 (3)
N1	0.0227 (4)	0.0154 (4)	0.0144 (4)	−0.0033 (3)	0.0100 (3)	−0.0004 (3)
N2	0.0195 (4)	0.0164 (4)	0.0166 (4)	−0.0041 (3)	0.0070 (3)	0.0013 (3)
C1	0.0175 (5)	0.0137 (4)	0.0136 (4)	0.0006 (4)	0.0082 (4)	−0.0006 (3)
C2	0.0209 (5)	0.0175 (5)	0.0125 (4)	0.0000 (4)	0.0066 (4)	−0.0009 (4)
C3	0.0197 (5)	0.0172 (5)	0.0147 (4)	−0.0028 (4)	0.0058 (4)	−0.0029 (4)
C4	0.0172 (5)	0.0145 (5)	0.0176 (5)	−0.0006 (4)	0.0088 (4)	0.0002 (4)
C5	0.0183 (5)	0.0170 (5)	0.0130 (4)	−0.0004 (4)	0.0059 (4)	0.0011 (4)
C6	0.0168 (5)	0.0159 (5)	0.0131 (4)	−0.0014 (4)	0.0053 (4)	−0.0014 (3)
C7	0.0144 (4)	0.0150 (5)	0.0148 (4)	0.0015 (4)	0.0071 (4)	0.0006 (3)
C8	0.0190 (5)	0.0183 (5)	0.0149 (4)	−0.0017 (4)	0.0067 (4)	0.0015 (4)
C9	0.0174 (5)	0.0171 (5)	0.0134 (4)	−0.0021 (4)	0.0037 (4)	0.0007 (4)
C10	0.0160 (5)	0.0170 (5)	0.0170 (4)	0.0008 (4)	0.0055 (4)	0.0001 (4)
C11	0.0138 (4)	0.0193 (5)	0.0168 (4)	−0.0004 (4)	0.0057 (4)	0.0007 (4)
C12	0.0164 (5)	0.0155 (5)	0.0176 (4)	−0.0020 (4)	0.0060 (4)	0.0003 (4)
C13	0.0220 (5)	0.0177 (5)	0.0203 (5)	−0.0009 (4)	0.0109 (4)	−0.0020 (4)
C14	0.0229 (5)	0.0196 (5)	0.0186 (5)	−0.0038 (4)	0.0117 (4)	−0.0009 (4)
C15	0.0252 (5)	0.0206 (5)	0.0209 (5)	−0.0015 (4)	0.0096 (4)	0.0056 (4)
C16	0.0274 (6)	0.0153 (5)	0.0298 (6)	−0.0013 (4)	0.0158 (5)	−0.0019 (4)

Geometric parameters (Å, º) top

O1—C7	1.2310 (13)	C5—H5A	0.9300
O2—C4	1.3550 (12)	C6—H6A	0.9300
O2—C15	1.4246 (13)	C8—C9	1.4588 (15)
O3—C11	1.3656 (13)	C8—H8A	0.9300
O3—H1O3	0.87 (2)	C9—C14	1.3918 (15)
O4—C12	1.3631 (13)	C9—C10	1.4024 (15)
O4—C16	1.4300 (14)	C10—C11	1.3779 (15)
N1—C7	1.3523 (13)	C10—H10A	0.9300
N1—N2	1.3847 (12)	C11—C12	1.4046 (15)
N1—H1N1	0.887 (17)	C12—C13	1.3858 (15)
N2—C8	1.2808 (14)	C13—C14	1.3906 (15)
C1—C6	1.3930 (14)	C13—H13A	0.9300
C1—C2	1.3980 (14)	C14—H14A	0.9300
C1—C7	1.4877 (14)	C15—H15A	0.9600
C2—C3	1.3796 (15)	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C3—C4	1.3978 (14)	C16—H16A	0.9600
C3—H3A	0.9300	C16—H16B	0.9600
C4—C5	1.3907 (14)	C16—H16C	0.9600
C5—C6	1.3888 (14)

C4—O2—C15	117.11 (9)	C14—C9—C10	119.41 (10)
C11—O3—H1O3	107.6 (13)	C14—C9—C8	118.29 (10)
C12—O4—C16	115.78 (9)	C10—C9—C8	122.28 (10)
C7—N1—N2	119.91 (9)	C11—C10—C9	120.04 (10)
C7—N1—H1N1	121.5 (11)	C11—C10—H10A	120.0
N2—N1—H1N1	116.8 (11)	C9—C10—H10A	120.0
C8—N2—N1	113.42 (9)	O3—C11—C10	119.06 (10)
C6—C1—C2	118.77 (10)	O3—C11—C12	120.68 (10)
C6—C1—C7	123.40 (9)	C10—C11—C12	120.25 (10)
C2—C1—C7	117.83 (9)	O4—C12—C13	125.55 (10)
C3—C2—C1	120.90 (9)	O4—C12—C11	114.57 (9)
C3—C2—H2A	119.6	C13—C12—C11	119.88 (10)
C1—C2—H2A	119.6	C12—C13—C14	119.76 (10)
C2—C3—C4	119.85 (9)	C12—C13—H13A	120.1
C2—C3—H3A	120.1	C14—C13—H13A	120.1
C4—C3—H3A	120.1	C13—C14—C9	120.64 (10)
O2—C4—C5	124.53 (9)	C13—C14—H14A	119.7
O2—C4—C3	115.62 (9)	C9—C14—H14A	119.7
C5—C4—C3	119.85 (10)	O2—C15—H15A	109.5
C6—C5—C4	119.82 (9)	O2—C15—H15B	109.5
C6—C5—H5A	120.1	H15A—C15—H15B	109.5
C4—C5—H5A	120.1	O2—C15—H15C	109.5
C5—C6—C1	120.78 (9)	H15A—C15—H15C	109.5
C5—C6—H6A	119.6	H15B—C15—H15C	109.5
C1—C6—H6A	119.6	O4—C16—H16A	109.5
O1—C7—N1	123.74 (10)	O4—C16—H16B	109.5
O1—C7—C1	121.37 (9)	H16A—C16—H16B	109.5
N1—C7—C1	114.89 (9)	O4—C16—H16C	109.5
N2—C8—C9	122.15 (10)	H16A—C16—H16C	109.5
N2—C8—H8A	118.9	H16B—C16—H16C	109.5
C9—C8—H8A	118.9

C7—N1—N2—C8	−154.92 (10)	N1—N2—C8—C9	179.20 (9)
C6—C1—C2—C3	0.60 (16)	N2—C8—C9—C14	−158.09 (11)
C7—C1—C2—C3	−178.84 (10)	N2—C8—C9—C10	20.44 (16)
C1—C2—C3—C4	0.97 (17)	C14—C9—C10—C11	0.05 (15)
C15—O2—C4—C5	−0.76 (16)	C8—C9—C10—C11	−178.47 (9)
C15—O2—C4—C3	179.62 (10)	C9—C10—C11—O3	−178.69 (9)
C2—C3—C4—O2	177.65 (10)	C9—C10—C11—C12	1.23 (15)
C2—C3—C4—C5	−2.00 (16)	C16—O4—C12—C13	10.02 (15)
O2—C4—C5—C6	−178.16 (10)	C16—O4—C12—C11	−170.42 (9)
C3—C4—C5—C6	1.45 (16)	O3—C11—C12—O4	−1.02 (14)
C4—C5—C6—C1	0.14 (16)	C10—C11—C12—O4	179.07 (9)
C2—C1—C6—C5	−1.16 (16)	O3—C11—C12—C13	178.58 (10)
C7—C1—C6—C5	178.25 (10)	C10—C11—C12—C13	−1.34 (16)
N2—N1—C7—O1	−0.80 (16)	O4—C12—C13—C14	179.72 (10)
N2—N1—C7—C1	178.78 (9)	C11—C12—C13—C14	0.17 (16)
C6—C1—C7—O1	−155.95 (10)	C12—C13—C14—C9	1.11 (16)
C2—C1—C7—O1	23.46 (15)	C10—C9—C14—C13	−1.22 (16)
C6—C1—C7—N1	24.46 (14)	C8—C9—C14—C13	177.35 (10)
C2—C1—C7—N1	−156.13 (10)

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
O3—H1O3···O4	0.87 (2)	2.18 (2)	2.6692 (13)	115.9 (18)
N1—H1N1···O1ⁱ	0.887 (18)	1.992 (18)	2.8698 (13)	170.0 (16)
C8—H8A···O1ⁱ	0.93	2.47	3.2780 (15)	145
C15—H15C···Cg1ⁱⁱ	0.96	2.72	3.5664 (15)	148
C16—H16B···Cg1ⁱⁱⁱ	0.96	2.76	3.4366 (16)	128

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₄
M_r	300.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.1323 (19), 12.9727 (15), 9.6714 (12)
β (°)	113.213 (2)
V (Å³)	1398.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.58 × 0.30 × 0.07

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.942, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	14521, 3704, 3260
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.109, 1.03
No. of reflections	3704
No. of parameters	208
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.23

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
O3—H1O3···O4	0.87 (2)	2.18 (2)	2.6692 (13)	115.9 (18)
N1—H1N1···O1ⁱ	0.887 (18)	1.992 (18)	2.8698 (13)	170.0 (16)
C8—H8A···O1ⁱ	0.93	2.47	3.2780 (15)	145
C15—H15C···Cg1ⁱⁱ	0.96	2.72	3.5664 (15)	148
C16—H16B···Cg1ⁱⁱⁱ	0.96	2.76	3.4366 (16)	128

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

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

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. The authors also thank the Prince of Songkla University and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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Volume 67| Part 12| December 2011| Pages o3370-o3371

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