(E)-N′-(3,4-Dimeth­oxy­benzyl­idene)-4-meth­oxy­benzohydrazide

Taha, M.; Naz, H.; Rahman, A.A.; Ismail, N.H.; Sammer, Y.

doi:10.1107/S1600536812034228

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2780

doi:10.1107/S1600536812034228

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(E)-N′-(3,4-Dimethoxybenzylidene)-4-methoxybenzohydrazide

Muhammad Taha,^a Humera Naz,^a,^b Aqilah Abd Rahman,^a,^b Nor Hadiani Ismail ^a and Yousuf Sammer ^c ^*

^aAtta-ur-Rahman Research Institute for Natural Products Discovery (RiND), Universiti Tecknologi MARA, Puncak Alam, 42300 Selangor, Malaysia, ^bFaculty of Pharmacy, Universiti Tecknologi MARA, Puncak Alam, 42300 Selangor, Malaysia, and ^cH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
^*Correspondence e-mail: dr.sammer.yousuf@gmail.com

(Received 27 July 2012; accepted 1 August 2012; online 25 August 2012)

In the title compound, C₁₇H₁₈N₂O₄, the azomethine double bond adopts an E conformation with an N—N—C—C torsion angle of −178.3 (3)°. The benzene rings are almost coplaner, with a dihedral angle of 2.98 (14)° between their mean planes. In the crystal, the molecules are linked by N—H⋯O hydrogen bonds, resulting in chains of molecules lying parallel to the b axis. The structure is further consolidated by rather weak C—H⋯O hydrogen-bonding interactions, resulting in six-membered rings about inversion centers linked into chains arranged parallel to the b axis.

Related literature

For the biological activity of benzohydrazides, see: Bayrak et al. (2009 ). For the crystal structures of related benzohydrazides, see: Fun et al. (2011 ); Lu et al. (2009 .

Experimental

Crystal data

C₁₇H₁₈N₂O₄
M_r = 314.33
Monoclinic, P 2₁ /c
a = 14.191 (2) Å
b = 5.0109 (8) Å
c = 22.535 (4) Å
β = 99.010 (4)°
V = 1582.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.23 × 0.20 × 0.04 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.979, T_max = 0.996
8638 measured reflections
2891 independent reflections
1400 reflections with I > 2σ(I)
R_int = 0.080

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.115
S = 0.96
2891 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3ⁱ	0.92 (3)	1.99 (3)	2.890 (4)	166 (2)
C15—H15A⋯O4ⁱⁱ	0.96	2.54	3.357 (4)	143
C17—H17A⋯O2ⁱⁱⁱ	0.96	2.55	3.505 (4)	172
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y, -z+2; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034228/pv2573sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812034228/pv2573Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812034228/pv2573Isup3.cml

checkCIF report

Comment top

Benzohydrazones play an imperative part in research due to their diverse structural features and wide range of biological activities such as antibacterial, antifungal, cytotoxic, anticonvulsant, antiplatelets, anticancer, antinflammatory, and analgesic (Bayrak et al., 2009). The title compound was prepared as a part of our ongoing research on benzohydrazones in order to study their structural features responsible for varoius biological activities.

In the title molecule (Fig. 1), the azomethine double bond (C7═N1, 1.277 (4) Å) adopts an E configuration with a torsion angle N2–N1–C6–C7 -178.3 (3)°. The benzene rings (C1–C6 and C9–C14) are almost coplanner with dihedral angle 2.98 (14)° between their mean planes. The bond lengths and angles in the title compound are similar to those reported in structurally realted compounds (Fun et al., 2011; Lu et al., 2009). The crystal structure is stabilized by N2—H2A···O3 intermolecular hydrogen bonds resulting in chains of molecules lying parallel to the b–axis (Tab. 1 & Fig. 2). The structure is further consolidated by rather weak intermolecular hydrogen bonding interactions C15—H15A···O4 and C17—H17A···O2, the former resulting in six membered rings about inversion centers and the later forming chains arranged parallel to the b-axis.

Related literature top

For the biological activity of benzohydrazides, see: Bayrak et al. (2009). For the crystal structures of related benzohydrazides, see: Fun et al. (2011); Lu et al. (2009.

Experimental top

The title compound was synthesized by refluxing a mixture of 4-methoxybenzohydrazide (0.332 g, 2.0 mmol) and 3,4-dimethoxybenzaldehyde (0.332 g, 2.0 mmol) and a catalytical amount of acetic acid for 3 h in methanol (20 ml). The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was evaporated by vacuum to afford the title compound (0.496 g, 79% yield). The compound was recrystalize by slow evaporation of a methanol solution to afforded light yellow crystals suitable for single-crystal X-ray diffraction studies. All chemicals were purchased from Sigma-Aldrich Germany.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.

Fig. 2. A view of the hydrogen bonding interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

(E)-N'-(3,4-Dimethoxybenzylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₇H₁₈N₂O₄	F(000) = 664
M_r = 314.33	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 506 reflections
a = 14.191 (2) Å	θ = 2.9–18.7°
b = 5.0109 (8) Å	µ = 0.10 mm⁻¹
c = 22.535 (4) Å	T = 273 K
β = 99.010 (4)°	Plate, colorles
V = 1582.7 (5) Å³	0.23 × 0.20 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2891 independent reflections
Radiation source: fine-focus sealed tube	1400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
ω scan	θ_max = 25.5°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −17→16
T_min = 0.979, T_max = 0.996	k = −5→5
8638 measured reflections	l = −27→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0319P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
2891 reflections	Δρ_max = 0.18 e Å⁻³
216 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0013 (5)

Crystal data top

C₁₇H₁₈N₂O₄	V = 1582.7 (5) Å³
M_r = 314.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.191 (2) Å	µ = 0.10 mm⁻¹
b = 5.0109 (8) Å	T = 273 K
c = 22.535 (4) Å	0.23 × 0.20 × 0.04 mm
β = 99.010 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	2891 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1400 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.996	R_int = 0.080
8638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.18 e Å⁻³
2891 reflections	Δρ_min = −0.16 e Å⁻³
216 parameters

Special details top

Geometry. 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.

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 > σ(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	0.08439 (16)	0.0973 (5)	0.30744 (8)	0.0533 (7)
O2	0.02249 (17)	−0.2411 (5)	0.37757 (9)	0.0517 (7)
O3	0.27009 (17)	−0.4724 (4)	0.67207 (9)	0.0559 (7)
O4	0.47170 (17)	−0.0216 (5)	0.92189 (8)	0.0597 (7)
N1	0.23561 (18)	−0.0850 (5)	0.58675 (10)	0.0423 (8)
N2	0.2763 (2)	−0.0366 (6)	0.64635 (11)	0.0429 (8)
C1	0.1311 (2)	−0.0799 (6)	0.46462 (12)	0.0383 (8)
H1B	0.1098	−0.2050	0.4900	0.046*
C2	0.0930 (2)	−0.0774 (6)	0.40460 (13)	0.0376 (8)
C3	0.1267 (2)	0.1102 (7)	0.36613 (12)	0.0390 (9)
C4	0.1959 (2)	0.2892 (6)	0.38871 (13)	0.0426 (9)
H4A	0.2185	0.4120	0.3634	0.051*
C5	0.2323 (2)	0.2866 (6)	0.44979 (13)	0.0447 (9)
H5A	0.2784	0.4110	0.4651	0.054*
C6	0.2013 (2)	0.1033 (7)	0.48788 (12)	0.0392 (9)
C7	0.2418 (2)	0.1119 (7)	0.55156 (13)	0.0435 (9)
H7A	0.2732	0.2658	0.5670	0.052*
C8	0.2912 (2)	−0.2397 (7)	0.68566 (13)	0.0380 (8)
C9	0.3389 (2)	−0.1642 (6)	0.74719 (12)	0.0330 (8)
C10	0.4038 (2)	0.0405 (6)	0.75824 (12)	0.0399 (9)
H10A	0.4164	0.1460	0.7265	0.048*
C11	0.4510 (2)	0.0934 (6)	0.81608 (12)	0.0401 (9)
H11A	0.4957	0.2301	0.8226	0.048*
C12	0.4308 (2)	−0.0582 (7)	0.86330 (13)	0.0395 (8)
C13	0.3653 (2)	−0.2629 (7)	0.85314 (13)	0.0468 (9)
H13A	0.3510	−0.3640	0.8852	0.056*
C14	0.3212 (2)	−0.3176 (6)	0.79592 (13)	0.0444 (9)
H14A	0.2787	−0.4597	0.7894	0.053*
C15	0.5404 (3)	0.1858 (7)	0.93508 (14)	0.0697 (12)
H15A	0.5626	0.1906	0.9776	0.105*
H15B	0.5116	0.3540	0.9224	0.105*
H15C	0.5932	0.1527	0.9142	0.105*
C16	−0.0236 (2)	−0.4110 (7)	0.41506 (13)	0.0567 (10)
H16A	−0.0743	−0.5066	0.3909	0.085*
H16B	−0.0494	−0.3050	0.4442	0.085*
H16C	0.0218	−0.5356	0.4353	0.085*
C17	0.1047 (3)	0.3085 (7)	0.26842 (13)	0.0626 (12)
H17A	0.0644	0.2907	0.2302	0.094*
H17B	0.1703	0.2987	0.2630	0.094*
H17C	0.0929	0.4774	0.2860	0.094*
H2A	0.2850 (18)	0.139 (5)	0.6573 (11)	0.030 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0620 (18)	0.0641 (18)	0.0305 (13)	−0.0093 (14)	−0.0034 (11)	0.0056 (12)
O2	0.0634 (18)	0.0525 (16)	0.0359 (13)	−0.0183 (14)	−0.0021 (12)	0.0002 (12)
O3	0.089 (2)	0.0261 (15)	0.0470 (14)	−0.0012 (13)	−0.0073 (12)	−0.0045 (12)
O4	0.0687 (19)	0.0761 (19)	0.0306 (13)	−0.0173 (15)	−0.0034 (11)	0.0017 (12)
N1	0.057 (2)	0.0356 (19)	0.0302 (15)	0.0044 (15)	−0.0065 (13)	−0.0070 (13)
N2	0.071 (2)	0.0230 (18)	0.0297 (15)	−0.0009 (16)	−0.0083 (13)	−0.0061 (14)
C1	0.049 (2)	0.031 (2)	0.0339 (18)	−0.0020 (18)	0.0027 (15)	0.0015 (15)
C2	0.044 (2)	0.034 (2)	0.0320 (18)	−0.0010 (18)	−0.0022 (15)	−0.0040 (16)
C3	0.042 (2)	0.045 (2)	0.0280 (18)	0.0055 (19)	0.0007 (15)	−0.0007 (17)
C4	0.045 (2)	0.045 (2)	0.0366 (19)	−0.0044 (18)	0.0030 (16)	0.0067 (16)
C5	0.049 (2)	0.040 (2)	0.042 (2)	−0.0053 (18)	−0.0050 (17)	−0.0007 (17)
C6	0.046 (2)	0.037 (2)	0.0331 (18)	0.0037 (18)	−0.0003 (16)	0.0000 (16)
C7	0.054 (3)	0.035 (2)	0.038 (2)	−0.0009 (19)	−0.0042 (17)	−0.0055 (17)
C8	0.050 (2)	0.027 (2)	0.0359 (19)	0.0054 (18)	0.0037 (16)	0.0010 (17)
C9	0.041 (2)	0.024 (2)	0.0337 (18)	0.0031 (16)	0.0054 (15)	−0.0005 (15)
C10	0.050 (2)	0.040 (2)	0.0301 (18)	−0.0014 (19)	0.0058 (15)	0.0014 (16)
C11	0.044 (2)	0.040 (2)	0.0349 (19)	−0.0064 (18)	0.0021 (15)	0.0005 (16)
C12	0.039 (2)	0.049 (2)	0.0289 (18)	0.0020 (19)	0.0016 (15)	−0.0004 (17)
C13	0.055 (3)	0.052 (2)	0.0323 (19)	−0.005 (2)	0.0052 (17)	0.0064 (17)
C14	0.055 (3)	0.033 (2)	0.045 (2)	−0.0077 (17)	0.0053 (17)	−0.0008 (17)
C15	0.077 (3)	0.081 (3)	0.043 (2)	−0.015 (3)	−0.015 (2)	−0.004 (2)
C16	0.051 (3)	0.065 (3)	0.054 (2)	−0.013 (2)	0.0067 (18)	−0.005 (2)
C17	0.073 (3)	0.069 (3)	0.045 (2)	0.008 (2)	0.003 (2)	0.018 (2)

Geometric parameters (Å, º) top

O1—C3	1.366 (3)	C7—H7A	0.9300
O1—C17	1.434 (3)	C8—C9	1.493 (4)
O2—C2	1.362 (3)	C9—C10	1.374 (4)
O2—C16	1.428 (3)	C9—C14	1.395 (4)
O3—C8	1.231 (3)	C10—C11	1.394 (4)
O4—C12	1.369 (3)	C10—H10A	0.9300
O4—C15	1.424 (4)	C11—C12	1.373 (4)
N1—C7	1.277 (4)	C11—H11A	0.9300
N1—N2	1.398 (3)	C12—C13	1.379 (4)
N2—C8	1.344 (4)	C13—C14	1.370 (4)
N2—H2A	0.92 (3)	C13—H13A	0.9300
C1—C2	1.376 (4)	C14—H14A	0.9300
C1—C6	1.395 (4)	C15—H15A	0.9600
C1—H1B	0.9300	C15—H15B	0.9600
C2—C3	1.412 (4)	C15—H15C	0.9600
C3—C4	1.367 (4)	C16—H16A	0.9600
C4—C5	1.393 (4)	C16—H16B	0.9600
C4—H4A	0.9300	C16—H16C	0.9600
C5—C6	1.375 (4)	C17—H17A	0.9600
C5—H5A	0.9300	C17—H17B	0.9600
C6—C7	1.460 (4)	C17—H17C	0.9600

C3—O1—C17	117.3 (3)	C9—C10—C11	121.4 (3)
C2—O2—C16	117.9 (2)	C9—C10—H10A	119.3
C12—O4—C15	118.2 (3)	C11—C10—H10A	119.3
C7—N1—N2	113.9 (3)	C12—C11—C10	119.4 (3)
C8—N2—N1	120.0 (3)	C12—C11—H11A	120.3
C8—N2—H2A	123.2 (16)	C10—C11—H11A	120.3
N1—N2—H2A	116.4 (16)	O4—C12—C11	124.4 (3)
C2—C1—C6	120.7 (3)	O4—C12—C13	115.6 (3)
C2—C1—H1B	119.6	C11—C12—C13	120.0 (3)
C6—C1—H1B	119.6	C14—C13—C12	120.1 (3)
O2—C2—C1	125.6 (3)	C14—C13—H13A	119.9
O2—C2—C3	115.0 (3)	C12—C13—H13A	119.9
C1—C2—C3	119.4 (3)	C13—C14—C9	121.2 (3)
O1—C3—C4	124.9 (3)	C13—C14—H14A	119.4
O1—C3—C2	115.0 (3)	C9—C14—H14A	119.4
C4—C3—C2	120.1 (3)	O4—C15—H15A	109.5
C3—C4—C5	119.7 (3)	O4—C15—H15B	109.5
C3—C4—H4A	120.2	H15A—C15—H15B	109.5
C5—C4—H4A	120.2	O4—C15—H15C	109.5
C6—C5—C4	121.2 (3)	H15A—C15—H15C	109.5
C6—C5—H5A	119.4	H15B—C15—H15C	109.5
C4—C5—H5A	119.4	O2—C16—H16A	109.5
C5—C6—C1	118.9 (3)	O2—C16—H16B	109.5
C5—C6—C7	118.6 (3)	H16A—C16—H16B	109.5
C1—C6—C7	122.4 (3)	O2—C16—H16C	109.5
N1—C7—C6	122.2 (3)	H16A—C16—H16C	109.5
N1—C7—H7A	118.9	H16B—C16—H16C	109.5
C6—C7—H7A	118.9	O1—C17—H17A	109.5
O3—C8—N2	123.1 (3)	O1—C17—H17B	109.5
O3—C8—C9	121.9 (3)	H17A—C17—H17B	109.5
N2—C8—C9	114.9 (3)	O1—C17—H17C	109.5
C10—C9—C14	117.8 (3)	H17A—C17—H17C	109.5
C10—C9—C8	123.4 (3)	H17B—C17—H17C	109.5
C14—C9—C8	118.7 (3)

C7—N1—N2—C8	−167.3 (3)	C1—C6—C7—N1	19.1 (5)
C16—O2—C2—C1	7.2 (5)	N1—N2—C8—O3	−0.4 (5)
C16—O2—C2—C3	−171.8 (3)	N1—N2—C8—C9	177.5 (3)
C6—C1—C2—O2	−178.0 (3)	O3—C8—C9—C10	146.6 (3)
C6—C1—C2—C3	1.1 (5)	N2—C8—C9—C10	−31.3 (5)
C17—O1—C3—C4	−8.7 (5)	O3—C8—C9—C14	−29.8 (5)
C17—O1—C3—C2	170.4 (3)	N2—C8—C9—C14	152.3 (3)
O2—C2—C3—O1	−0.7 (4)	C14—C9—C10—C11	0.4 (5)
C1—C2—C3—O1	−179.9 (3)	C8—C9—C10—C11	−176.0 (3)
O2—C2—C3—C4	178.4 (3)	C9—C10—C11—C12	−1.5 (5)
C1—C2—C3—C4	−0.7 (5)	C15—O4—C12—C11	−0.6 (5)
O1—C3—C4—C5	178.6 (3)	C15—O4—C12—C13	179.6 (3)
C2—C3—C4—C5	−0.4 (5)	C10—C11—C12—O4	−179.0 (3)
C3—C4—C5—C6	1.3 (5)	C10—C11—C12—C13	0.8 (5)
C4—C5—C6—C1	−1.0 (5)	O4—C12—C13—C14	−179.3 (3)
C4—C5—C6—C7	−179.6 (3)	C11—C12—C13—C14	0.9 (5)
C2—C1—C6—C5	−0.2 (5)	C12—C13—C14—C9	−2.0 (5)
C2—C1—C6—C7	178.4 (3)	C10—C9—C14—C13	1.4 (5)
N2—N1—C7—C6	−178.3 (3)	C8—C9—C14—C13	177.9 (3)
C5—C6—C7—N1	−162.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.92 (3)	1.99 (3)	2.890 (4)	166 (2)
C15—H15A···O4ⁱⁱ	0.96	2.54	3.357 (4)	143
C17—H17A···O2ⁱⁱⁱ	0.96	2.55	3.505 (4)	172

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₄
M_r	314.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	273
a, b, c (Å)	14.191 (2), 5.0109 (8), 22.535 (4)
β (°)	99.010 (4)
V (Å³)	1582.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.20 × 0.04

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.979, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	8638, 2891, 1400
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.115, 0.96
No. of reflections	2891
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3ⁱ	0.92 (3)	1.99 (3)	2.890 (4)	166 (2)
C15—H15A···O4ⁱⁱ	0.9600	2.5400	3.357 (4)	143.00
C17—H17A···O2ⁱⁱⁱ	0.9600	2.5500	3.505 (4)	172.00

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

References

Bayrak, H., Demirbas, N. & Karaoglu, S. A. (2009). Eur. J. Med. Chem. 44, 4362–4366. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Promdet, P., Chantrapromma, S., Horkaew, J. & Karalai, C. (2011). Acta Cryst. E67, o3370–o3371. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lu, J.-F., Min, S.-T., Ge, H.-G. & Ji, X.-H. (2009). Acta Cryst. E65, o2301. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. 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

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Volume 68| Part 9| September 2012| Page o2780

doi:10.1107/S1600536812034228

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