N-(4-Chloro­phen­yl)-3,4,5-trimethoxy­benzamide

Saeed, A.; Khera, R.A.; Batool, M.; Shaheen, U.; Flörke, U.

doi:10.1107/S1600536808023234

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1625

doi:10.1107/S1600536808023234

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N-(4-Chlorophenyl)-3,4,5-trimethoxybenzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Mahira Batool,^a Uzma Shaheen ^a and Ulrich Flörke ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan, and ^bDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 12 July 2008; accepted 23 July 2008; online 31 July 2008)

In the title compound, C₁₆H₁₆ClNO₄, the dihedral angle between the two aromatic rings is 67.33 (8)°. The crystal packing shows strong intermolecular N—H⋯O hydrogen bonds that link the molecules to form chains along [ $[\overline{1}]$ 01].

Related literature

For related literature, see: Capdeville et al. (2002 ); Ho et al. (2002 ); Igawa et al. (1999 ); Jackson et al. (1994 ); Makino et al. (2003 ); Zhichkin et al. (2007 ).

Experimental

Crystal data

C₁₆H₁₆ClNO₄
M_r = 321.75
Monoclinic, C c
a = 9.487 (2) Å
b = 25.666 (6) Å
c = 6.9781 (15) Å
β = 112.340 (5)°
V = 1571.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 (2) K
0.41 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.901, T_max = 0.975
6765 measured reflections
3581 independent reflections
3104 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.106
S = 1.02
3581 reflections
202 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), with 1780 Friedel pairs
Flack parameter: 0.06 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.18	2.878 (3)	136
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023234/bt2747sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023234/bt2747Isup2.hkl

checkCIF report

Comment top

The benzanilide core is present in compounds with a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), benzodiazepine-2,5-diones (Ho et al., 20022), and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic, have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002). Benzamides have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999)

Geometric parameters of the title compound, C₁₆H₁₆ClNO₄, are in the usual ranges. The dihedral angle between the two aromatic rings is 67.33 (8)° and the torsion angles N1—C1—C2—C3 and C1—N1—C11—C12 are -31.1 (3)° and -39.2 (4)°, respectively. Of the three methoxy groups two of them lie nearly in plane with the aromatic ring, the O(3) group is almost perpendicular with C9—O3—C5—C4 of 92.2 (3)°. The crystal packing shows strong intermolecular N—H···O bonds that link molecules to endless chains along [-101]. Details are given in Table 1.

Related literature top

For related literature, see: Capdeville et al. (2002); Ho et al. (2002); Igawa et al. (1999); Jackson et al. (1994); Makino et al. (2003); Zhichkin et al. (2007).

Experimental top

Trimethoxybenzoyl chloride (5.4 mmol) in CHCl₃ was treated with 4-chloroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with aq 1 M HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl₃ afforded the title compound (84%) as white needles: IR (KBr) 3226, 1665, 1616, 1520, 1352 cm^-1; 1H NMR (CDCl₃, 400 MHz) δ 8.13 (d, J = 8 Hz, 1H), 7.81 (d, J = 8 Hz, 1H), 7.51 (dd, J = 8 Hz, 1H), 7.66 (dd, J = 8 Hz, 1H), 7.43 (d, J = 8 Hz, 2H), 7.36 (br s, 1H), 7.25 (d, J = 8 Hz, 1H), 3.89 (9H, s, OMex3). Anal. Calcd. For C₁₆H₁₆ClNO₄, C, 59.73; H, 5.01; 11.02; N, 4.35; found C, 59.69; H, 5.04; 11.02; N, 4.42

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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).

Figures top

	Fig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along [001] with intermolecular hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted.

N-(4-Chlorophenyl)-3,4,5-trimethoxybenzamide top

Crystal data top

C₁₆H₁₆ClNO₄	F(000) = 672
M_r = 321.75	D_x = 1.360 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 879 reflections
a = 9.487 (2) Å	θ = 2.5–26.6°
b = 25.666 (6) Å	µ = 0.26 mm⁻¹
c = 6.9781 (15) Å	T = 120 K
β = 112.340 (5)°	Prism, colourless
V = 1571.5 (6) Å³	0.41 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3581 independent reflections
Radiation source: sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.9°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −12→12
T_min = 0.901, T_max = 0.975	k = −33→29
6765 measured reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0463P)² + 0.1374P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3581 reflections	Δρ_max = 0.33 e Å⁻³
202 parameters	Δρ_min = −0.24 e Å⁻³
2 restraints	Absolute structure: Flack (1983), with 1780 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.06 (6)

Crystal data top

C₁₆H₁₆ClNO₄	V = 1571.5 (6) Å³
M_r = 321.75	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 9.487 (2) Å	µ = 0.26 mm⁻¹
b = 25.666 (6) Å	T = 120 K
c = 6.9781 (15) Å	0.41 × 0.10 × 0.10 mm
β = 112.340 (5)°

Data collection top

Bruker SMART APEX diffractometer	3581 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3104 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.975	R_int = 0.040
6765 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.106	Δρ_max = 0.33 e Å⁻³
S = 1.02	Δρ_min = −0.24 e Å⁻³
3581 reflections	Absolute structure: Flack (1983), with 1780 Friedel pairs
202 parameters	Absolute structure parameter: 0.06 (6)
2 restraints

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
Cl1	0.24506 (8)	0.52096 (2)	−0.45259 (9)	0.03098 (17)
O1	0.0700 (2)	0.75731 (7)	−0.2052 (3)	0.0251 (4)
O2	0.3495 (2)	0.83040 (7)	0.6718 (3)	0.0293 (4)
O3	0.2739 (2)	0.92522 (7)	0.5093 (3)	0.0287 (4)
O4	0.1760 (2)	0.94204 (7)	0.1029 (3)	0.0293 (4)
N1	0.2656 (2)	0.71265 (7)	0.0305 (3)	0.0206 (4)
H1	0.3366	0.7136	0.1562	0.025*
C1	0.1742 (3)	0.75494 (10)	−0.0350 (4)	0.0201 (5)
C2	0.2087 (3)	0.79915 (9)	0.1153 (4)	0.0190 (5)
C3	0.2689 (3)	0.79115 (10)	0.3293 (4)	0.0207 (5)
H3A	0.2926	0.7570	0.3846	0.025*
C4	0.2938 (3)	0.83381 (10)	0.4601 (4)	0.0217 (5)
C5	0.2589 (3)	0.88383 (10)	0.3797 (4)	0.0217 (5)
C6	0.2015 (3)	0.89163 (10)	0.1650 (4)	0.0226 (6)
C7	0.1739 (3)	0.84890 (9)	0.0330 (4)	0.0209 (5)
H7A	0.1314	0.8538	−0.1129	0.025*
C8	0.4275 (4)	0.78426 (12)	0.7598 (5)	0.0380 (7)
H8A	0.3560	0.7549	0.7223	0.057*
H8B	0.4727	0.7878	0.9109	0.057*
H8C	0.5083	0.7779	0.7073	0.057*
C9	0.4195 (4)	0.94971 (13)	0.5730 (6)	0.0457 (8)
H9A	0.4986	0.9251	0.6541	0.069*
H9B	0.4213	0.9803	0.6582	0.069*
H9C	0.4387	0.9606	0.4506	0.069*
C10	0.1094 (4)	0.95144 (11)	−0.1151 (5)	0.0375 (7)
H10A	0.1764	0.9377	−0.1807	0.056*
H10B	0.0960	0.9890	−0.1405	0.056*
H10C	0.0100	0.9341	−0.1736	0.056*
C11	0.2554 (3)	0.66682 (9)	−0.0888 (4)	0.0194 (5)
C12	0.1169 (3)	0.64558 (10)	−0.2157 (4)	0.0238 (5)
H12A	0.0244	0.6618	−0.2258	0.029*
C13	0.1133 (3)	0.60093 (10)	−0.3273 (4)	0.0269 (6)
H13A	0.0184	0.5868	−0.4158	0.032*
C14	0.2479 (3)	0.57674 (10)	−0.3103 (4)	0.0218 (5)
C15	0.3862 (3)	0.59685 (10)	−0.1809 (4)	0.0259 (6)
H15A	0.4784	0.5798	−0.1675	0.031*
C16	0.3897 (3)	0.64200 (10)	−0.0706 (4)	0.0250 (6)
H16A	0.4847	0.6561	0.0182	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0333 (3)	0.0268 (3)	0.0286 (3)	0.0033 (3)	0.0071 (3)	−0.0101 (3)
O1	0.0181 (9)	0.0240 (10)	0.0225 (9)	0.0011 (7)	−0.0043 (7)	−0.0031 (7)
O2	0.0373 (11)	0.0277 (10)	0.0193 (9)	0.0051 (8)	0.0066 (8)	0.0008 (8)
O3	0.0346 (11)	0.0236 (9)	0.0262 (10)	−0.0009 (8)	0.0097 (8)	−0.0075 (8)
O4	0.0406 (12)	0.0171 (9)	0.0248 (10)	0.0013 (8)	0.0062 (9)	0.0014 (8)
N1	0.0170 (10)	0.0186 (10)	0.0186 (10)	0.0016 (8)	−0.0019 (8)	−0.0021 (9)
C1	0.0157 (11)	0.0203 (12)	0.0207 (13)	−0.0004 (9)	0.0026 (11)	−0.0003 (10)
C2	0.0154 (12)	0.0179 (12)	0.0214 (13)	−0.0006 (9)	0.0046 (10)	−0.0017 (10)
C3	0.0172 (11)	0.0188 (12)	0.0221 (13)	−0.0002 (9)	0.0027 (10)	0.0033 (10)
C4	0.0218 (13)	0.0241 (14)	0.0184 (13)	−0.0003 (10)	0.0068 (11)	−0.0015 (10)
C5	0.0218 (12)	0.0203 (13)	0.0230 (13)	−0.0009 (10)	0.0085 (11)	−0.0056 (10)
C6	0.0227 (13)	0.0181 (13)	0.0248 (14)	0.0016 (10)	0.0065 (11)	0.0010 (10)
C7	0.0192 (11)	0.0211 (13)	0.0187 (12)	0.0010 (9)	0.0029 (10)	0.0005 (10)
C8	0.052 (2)	0.0397 (17)	0.0211 (14)	0.0166 (15)	0.0126 (14)	0.0076 (13)
C9	0.0401 (18)	0.0386 (18)	0.050 (2)	−0.0104 (14)	0.0079 (16)	−0.0163 (15)
C10	0.058 (2)	0.0190 (14)	0.0282 (15)	0.0046 (13)	0.0084 (14)	0.0044 (12)
C11	0.0225 (12)	0.0159 (12)	0.0161 (11)	−0.0007 (9)	0.0031 (10)	0.0018 (9)
C12	0.0176 (12)	0.0218 (13)	0.0294 (14)	0.0030 (10)	0.0059 (11)	−0.0023 (11)
C13	0.0200 (13)	0.0283 (15)	0.0255 (14)	−0.0029 (10)	0.0011 (11)	−0.0080 (11)
C14	0.0286 (13)	0.0161 (12)	0.0209 (13)	0.0003 (10)	0.0095 (11)	−0.0039 (10)
C15	0.0208 (13)	0.0263 (14)	0.0285 (14)	0.0057 (10)	0.0069 (11)	0.0015 (11)
C16	0.0191 (13)	0.0233 (14)	0.0255 (14)	−0.0013 (10)	0.0005 (11)	−0.0014 (11)

Geometric parameters (Å, º) top

Cl1—C14	1.737 (2)	C8—H8A	0.9800
O1—C1	1.225 (3)	C8—H8B	0.9800
O2—C4	1.369 (3)	C8—H8C	0.9800
O2—C8	1.408 (3)	C9—H9A	0.9800
O3—C5	1.367 (3)	C9—H9B	0.9800
O3—C9	1.426 (4)	C9—H9C	0.9800
O4—C6	1.357 (3)	C10—H10A	0.9800
O4—C10	1.429 (4)	C10—H10B	0.9800
N1—C1	1.356 (3)	C10—H10C	0.9800
N1—C11	1.423 (3)	C11—C16	1.386 (4)
N1—H1	0.8800	C11—C12	1.386 (4)
C1—C2	1.494 (3)	C12—C13	1.378 (4)
C2—C7	1.387 (3)	C12—H12A	0.9500
C2—C3	1.397 (4)	C13—C14	1.384 (4)
C3—C4	1.387 (3)	C13—H13A	0.9500
C3—H3A	0.9500	C14—C15	1.380 (4)
C4—C5	1.390 (4)	C15—C16	1.385 (4)
C5—C6	1.400 (3)	C15—H15A	0.9500
C6—C7	1.392 (4)	C16—H16A	0.9500
C7—H7A	0.9500

C4—O2—C8	116.6 (2)	H8B—C8—H8C	109.5
C5—O3—C9	113.2 (2)	O3—C9—H9A	109.5
C6—O4—C10	117.0 (2)	O3—C9—H9B	109.5
C1—N1—C11	124.9 (2)	H9A—C9—H9B	109.5
C1—N1—H1	117.5	O3—C9—H9C	109.5
C11—N1—H1	117.5	H9A—C9—H9C	109.5
O1—C1—N1	123.0 (2)	H9B—C9—H9C	109.5
O1—C1—C2	121.6 (2)	O4—C10—H10A	109.5
N1—C1—C2	115.5 (2)	O4—C10—H10B	109.5
C7—C2—C3	120.9 (2)	H10A—C10—H10B	109.5
C7—C2—C1	117.0 (2)	O4—C10—H10C	109.5
C3—C2—C1	122.0 (2)	H10A—C10—H10C	109.5
C4—C3—C2	119.1 (2)	H10B—C10—H10C	109.5
C4—C3—H3A	120.5	C16—C11—C12	119.5 (2)
C2—C3—H3A	120.5	C16—C11—N1	118.1 (2)
O2—C4—C3	124.0 (2)	C12—C11—N1	122.4 (2)
O2—C4—C5	115.4 (2)	C13—C12—C11	120.1 (2)
C3—C4—C5	120.6 (2)	C13—C12—H12A	119.9
O3—C5—C4	120.1 (2)	C11—C12—H12A	119.9
O3—C5—C6	119.8 (2)	C12—C13—C14	120.0 (2)
C4—C5—C6	120.0 (2)	C12—C13—H13A	120.0
O4—C6—C7	125.0 (2)	C14—C13—H13A	120.0
O4—C6—C5	115.3 (2)	C15—C14—C13	120.3 (2)
C7—C6—C5	119.6 (2)	C15—C14—Cl1	119.1 (2)
C2—C7—C6	119.7 (2)	C13—C14—Cl1	120.5 (2)
C2—C7—H7A	120.1	C14—C15—C16	119.5 (2)
C6—C7—H7A	120.1	C14—C15—H15A	120.2
O2—C8—H8A	109.5	C16—C15—H15A	120.2
O2—C8—H8B	109.5	C15—C16—C11	120.5 (2)
H8A—C8—H8B	109.5	C15—C16—H16A	119.8
O2—C8—H8C	109.5	C11—C16—H16A	119.8
H8A—C8—H8C	109.5

C11—N1—C1—O1	1.5 (4)	O3—C5—C6—O4	5.1 (3)
C11—N1—C1—C2	−178.5 (2)	C4—C5—C6—O4	−177.9 (2)
O1—C1—C2—C7	−29.2 (3)	O3—C5—C6—C7	−174.4 (2)
N1—C1—C2—C7	150.8 (2)	C4—C5—C6—C7	2.6 (4)
O1—C1—C2—C3	148.9 (2)	C3—C2—C7—C6	1.1 (4)
N1—C1—C2—C3	−31.1 (3)	C1—C2—C7—C6	179.2 (2)
C7—C2—C3—C4	0.0 (4)	O4—C6—C7—C2	178.2 (2)
C1—C2—C3—C4	−178.0 (2)	C5—C6—C7—C2	−2.4 (4)
C8—O2—C4—C3	19.9 (4)	C1—N1—C11—C16	143.0 (3)
C8—O2—C4—C5	−161.6 (3)	C1—N1—C11—C12	−39.2 (4)
C2—C3—C4—O2	178.7 (2)	C16—C11—C12—C13	−1.8 (4)
C2—C3—C4—C5	0.2 (4)	N1—C11—C12—C13	−179.6 (2)
C9—O3—C5—C4	92.2 (3)	C11—C12—C13—C14	1.0 (4)
C9—O3—C5—C6	−90.8 (3)	C12—C13—C14—C15	0.5 (4)
O2—C4—C5—O3	−3.1 (3)	C12—C13—C14—Cl1	−179.1 (2)
C3—C4—C5—O3	175.5 (2)	C13—C14—C15—C16	−1.1 (4)
O2—C4—C5—C6	179.8 (2)	Cl1—C14—C15—C16	178.5 (2)
C3—C4—C5—C6	−1.6 (4)	C14—C15—C16—C11	0.3 (4)
C10—O4—C6—C7	2.9 (4)	C12—C11—C16—C15	1.2 (4)
C10—O4—C6—C5	−176.6 (3)	N1—C11—C16—C15	179.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.18	2.878 (3)	136

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆ClNO₄
M_r	321.75
Crystal system, space group	Monoclinic, Cc
Temperature (K)	120
a, b, c (Å)	9.487 (2), 25.666 (6), 6.9781 (15)
β (°)	112.340 (5)
V (Å³)	1571.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.41 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.901, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	6765, 3581, 3104
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.106, 1.02
No. of reflections	3581
No. of parameters	202
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.24
Absolute structure	Flack (1983), with 1780 Friedel pairs
Absolute structure parameter	0.06 (6)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.18	2.878 (3)	135.6

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Acknowledgements

AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Capdeville, R., Buchdunger, E. Zimmermann, J. & Matter, A. (2002). Nature Rev. Drug Discov. 1, 493–502. Web of Science CrossRef CAS Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ho, T.-I., Chen, W.-S., Hsu, C.-W., Tsai, Y.-M. & Fang, J.-M. (2002). Heterocycles, 57, 1501–1506. CrossRef CAS Google Scholar
Igawa, H., Nishimura, M., Okada, K. & Nakamura, T. (1999). Jpn. Patent Kokai Tokkyo Koho JP 11171848. Google Scholar
Jackson, S., DeGrado, W., Dwivedi, A., Parthasarathy, A., Higley, A., Krywko, J., Rockwell, A., Markwalder, J., Wells, G., Wexler, R., Mousa, S. & Harlow, R. (1994). J. Am. Chem. Soc. 116, 3220–3230. CSD CrossRef CAS Web of Science Google Scholar
Makino, S., Nakanishi, E. & Tsuji, T. (2003). Bull. Korean Chem. Soc. 24, 389–392. CAS Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett. 9, 1415–1418. Web of Science CrossRef PubMed CAS Google Scholar