2-Bromo-N′-[(2Z)-butan-2-yl­idene]-5-methoxy­benzohydrazide

Jasinski, J.P.; Butcher, R.J.; Suchitra, L.P.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536809044869

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2968-o2969

https://doi.org/10.1107/S1600536809044869

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2-Bromo-N′-[(2Z)-butan-2-ylidene]-5-methoxybenzohydrazide

Jerry P. Jasinski,^a Ray J. Butcher,^b ^* L. P. Suchitra,^c H. S. Yathirajan ^c and B. Narayana ^d

^aDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^dDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 26 October 2009; accepted 27 October 2009; online 31 October 2009)

In the title compound, C₁₂H₁₅BrN₂O₂, the dihedral angle between the benzene ring and the mean plane of the amide grouping is 77.7 (8)°. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds occur, and the packing is further supported by C—H⋯O and C—H⋯Br interactions and weak π–π ring stacking interactions.

Related literature

Hydrazides and their corresponding Schiff bases are useful precursors in the synthesis of several heterocyclic systems, see: Narayana et al. (2005 ; 2005a ). For the biological activity of substituted hydrazides, see: Cajocorius et al. (1977 ). Hydrazides are intermediates in the production of many pharmaceutically important compounds, see: Liu et al. (2006 ). For related structures, see: Butcher et al. (2007 ); Hou (2009 ); Li & Ban (2009 ); Sarojini et al. (2007a ,b ,c ,d ). For the MOPAC AM1 calculations, see: Schmidt & Polik (2007 ).

Experimental

Crystal data

C₁₂H₁₅BrN₂O₂
M_r = 299.17
Monoclinic, P 2₁ /c
a = 8.0942 (1) Å
b = 14.2475 (2) Å
c = 11.2974 (2) Å
β = 91.1519 (13)°
V = 1302.58 (3) Å³
Z = 4
Cu Kα radiation
μ = 4.25 mm⁻¹
T = 200 K
0.56 × 0.47 × 0.35 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.452, T_max = 1.000
7962 measured reflections
2577 independent reflections
2484 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.122
S = 1.07
2577 reflections
157 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −1.07 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O2ⁱ	0.98	2.60	3.561 (4)	166
C10—H10A⋯Brⁱⁱ	0.98	3.07	3.949 (5)	151
C10—H10A⋯O2ⁱⁱⁱ	0.98	2.55	3.231 (4)	127
C11—H11A⋯O1^iv	0.99	2.55	3.373 (4)	141
N1—H1A⋯O2ⁱⁱⁱ	0.88	2.07	2.932 (3)	165
Symmetry codes: (i) -x, -y+2, -z; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+2, -z+1; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis Pro (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis Pro and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; 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 global, I. DOI: https://doi.org/10.1107/S1600536809044869/ds2010sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809044869/ds2010Isup2.hkl

checkCIF report

Comment top

Hydrazides and the corresponding Schiff bases are useful precursors in the synthesis of several heterocyclic systems (Narayana et al. 2005; 2005a). Some substituted hydrazides are reported to exhibit carcinostatic activity against several types of tumors (Cajocorius et al. 1977) and also possess antimicrobial activity. It is also used as an intermediate in many pharmaceutically important compounds (Liu et al. 2006). In continuation with our studies on the structures of hydrazides and their Schiff bases (Sarojini et al. 2007a, 2007b, 2007c, 2007d; Butcher et al. 2007) a new Schiff base, (I), C₁₂H₁5BrN₂O₂, has been synthesized and its crystal structure is now reported.

In the title compound, C₁₂H₁5BrN₂O₂, (Fig. 1), the 2-bromo and 5-methoxy groups are in the plane of the benzene ring. The dihedral angle between the mean planes of the carbonyl group (–C6—C8(O2)—N1—N2-) and benzene ring is 77.7 (8)°. The C1—C6—C8—O2 and C1—C6—C8—N1 torsion angles (-101.1 (3)° & -103.7 (3)°) support this observation. Crystal packing is supported by a collection of intermediate N1—H1A—O2 (-x,-y + 2,-z + 1) intermolecular interactions (see Table 1) which produces a cooperative network of infinite O—H···O—H···O—H chains arranged diagonally along the (101) plane of the unit cell (Fig. 2). In addition, weak intermolecular C10—H10A···O2 (-x,-y + 2,-z + 1), C11—H11A···O1 (-x + 1, y - 1/2,-z + 1/2), C7—H7B···O2 (-x,-y + 2,-z) and C10—H10A···Br (x,-y + 3/2,z1/2) interactions (Table 1) along with Cg1···Cg1 π-π ring stacking interactions at 3.869 (1)Å (2 - x,1 - y,1 - z; slippage = 1.43 (2) Å, where Cg1 = C1—C6), collectively, slightly influence crystal packing in this crystalline environment.

After a MOPAC AM1 computational calculation (Schmidt, 2007), the dihedral angle between the mean planes of the carbonyl group (–C6—C8(O2)—N1—N2-) and benzene ring becomes 84.0 (8)°, significantly greater that the 77.7 (8)° seen in the crystal. This supports the observation of a collective action of the intermediate and weak hydrogen bond interactions along with weak intermolecular π-π stacking interactions which influence crystal packing stability.

Related literature top

Hydrazides and the corresponding Schiff bases are useful precursors in the synthesis of several heterocyclic systems, see: Narayana et al. (2005; 2005a). For the biological activity of substituted hydrazides, see: Cajocorius et al. (1977). Hydrazides are intermediates in the production of many pharmaceutically important compounds, see: Liu et al. (2006). For related structures, see: Butcher et al. (2007); Hou (2009); Li & Ban (2009); Sarojini et al. (2007a,b,c,d). For the MOPAC AM1 computational calculation, see: Schmidt & Polik (2007).

Experimental top

A mixture of 2-bromo-5-methoxybenzohydrazide (2.45 g, 0.01 mol) and ethyl methyl ketone(1.44 g, 0.02 mol) in 20 ml of ethanol containing a drop of dilute sulfuric acid was refluxed for about 2 h (Scheme 2). On cooling, the solid separated was filtered and recrystallized from ethyl methyl ketone. M.P.: 385 K. Analysis for C₁₂H₁₅BrN₂O₂: Found (Calculated): C: 48.14 (48.18); H: 5.02 (5.05%); N: 9.31 (9.36%).

Structure description top

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); 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 C₁₂H₁5BrN₂O₂ showing atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, (I), viewed down the b axis. Dashed lines indicate intermediate intermolecular N—H···O and C—H···O interactions which produces a network of infinite O—H···O—H···O—H chains arranged diagonally along the (101) plane of the unit cell.

2-Bromo-N'-[(2Z)-butan-2-ylidene]-5-methoxybenzohydrazide top

Crystal data top

C₁₂H₁₅BrN₂O₂	F(000) = 608
M_r = 299.17	D_x = 1.526 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 8517 reflections
a = 8.0942 (1) Å	θ = 5.0–73.4°
b = 14.2475 (2) Å	µ = 4.25 mm⁻¹
c = 11.2974 (2) Å	T = 200 K
β = 91.1519 (13)°	Chunk, colorless
V = 1302.58 (3) Å³	0.56 × 0.47 × 0.35 mm
Z = 4

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	2577 independent reflections
Radiation source: fine-focus sealed tube	2484 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 10.5081 pixels mm^-1	θ_max = 73.6°, θ_min = 5.0°
φ and ω scans	h = −10→9
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −16→17
T_min = 0.452, T_max = 1.000	l = −9→13
7962 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0673P)² + 1.7115P] where P = (F_o² + 2F_c²)/3
2577 reflections	(Δ/σ)_max < 0.001
157 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −1.07 e Å⁻³

Crystal data top

C₁₂H₁₅BrN₂O₂	V = 1302.58 (3) Å³
M_r = 299.17	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.0942 (1) Å	µ = 4.25 mm⁻¹
b = 14.2475 (2) Å	T = 200 K
c = 11.2974 (2) Å	0.56 × 0.47 × 0.35 mm
β = 91.1519 (13)°

Data collection top

Oxford Diffraction Gemini R CCD diffractometer	2577 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2484 reflections with I > 2σ(I)
T_min = 0.452, T_max = 1.000	R_int = 0.023
7962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.07	Δρ_max = 0.73 e Å⁻³
2577 reflections	Δρ_min = −1.07 e Å⁻³
157 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
Br	−0.00062 (5)	0.75926 (3)	0.23886 (3)	0.05362 (18)
O1	0.3113 (3)	1.07458 (17)	−0.03054 (18)	0.0478 (6)
O2	−0.0433 (2)	1.01275 (15)	0.35066 (16)	0.0358 (5)
N1	0.1775 (3)	0.93324 (16)	0.42004 (18)	0.0306 (5)
H1A	0.1550	0.9465	0.4941	0.037*
N2	0.3148 (3)	0.87860 (17)	0.39363 (19)	0.0318 (5)
C1	0.0954 (3)	0.85866 (18)	0.1528 (2)	0.0305 (5)
C2	0.1316 (4)	0.8445 (2)	0.0351 (2)	0.0361 (6)
H2A	0.1073	0.7858	−0.0012	0.043*
C3	0.2033 (3)	0.9154 (2)	−0.0303 (2)	0.0316 (6)
H3A	0.2285	0.9056	−0.1111	0.038*
C4	0.2379 (3)	1.00067 (19)	0.0234 (2)	0.0294 (5)
C5	0.1981 (3)	1.01479 (18)	0.1415 (2)	0.0285 (5)
H5A	0.2195	1.0739	0.1775	0.034*
C6	0.1282 (3)	0.94403 (17)	0.2066 (2)	0.0244 (5)
C7	0.3619 (4)	1.0618 (3)	−0.1501 (3)	0.0525 (9)
H7A	0.4202	1.1181	−0.1766	0.079*
H7B	0.2644	1.0512	−0.2012	0.079*
H7C	0.4357	1.0075	−0.1544	0.079*
C8	0.0802 (3)	0.96538 (18)	0.3318 (2)	0.0258 (5)
C9	0.4048 (3)	0.8504 (2)	0.4794 (2)	0.0357 (6)
C10	0.3829 (5)	0.8738 (3)	0.6083 (3)	0.0624 (12)
H10A	0.2676	0.8632	0.6295	0.094*
H10B	0.4118	0.9397	0.6221	0.094*
H10C	0.4551	0.8336	0.6570	0.094*
C11	0.5478 (4)	0.7880 (3)	0.4479 (3)	0.0485 (8)
H11A	0.5308	0.7253	0.4835	0.058*
H11B	0.5486	0.7800	0.3609	0.058*
C12	0.7109 (5)	0.8246 (4)	0.4882 (5)	0.0764 (13)
H12A	0.7969	0.7786	0.4702	0.115*
H12B	0.7097	0.8357	0.5738	0.115*
H12C	0.7339	0.8837	0.4472	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0949 (4)	0.0345 (2)	0.0315 (2)	−0.01786 (16)	0.00182 (18)	0.00284 (12)
O1	0.0666 (14)	0.0508 (13)	0.0261 (11)	−0.0214 (11)	0.0079 (9)	−0.0005 (9)
O2	0.0396 (10)	0.0467 (12)	0.0210 (9)	0.0198 (8)	−0.0009 (7)	−0.0063 (8)
N1	0.0373 (11)	0.0386 (12)	0.0159 (10)	0.0145 (9)	0.0007 (8)	−0.0042 (8)
N2	0.0371 (11)	0.0346 (12)	0.0238 (11)	0.0125 (9)	0.0026 (9)	−0.0023 (9)
C1	0.0452 (14)	0.0245 (12)	0.0219 (12)	0.0002 (10)	0.0004 (10)	−0.0003 (10)
C2	0.0576 (17)	0.0292 (13)	0.0212 (13)	0.0033 (12)	−0.0032 (11)	−0.0081 (10)
C3	0.0397 (13)	0.0395 (15)	0.0157 (11)	0.0066 (11)	0.0019 (9)	−0.0066 (10)
C4	0.0322 (12)	0.0352 (14)	0.0206 (12)	−0.0005 (10)	−0.0021 (10)	−0.0007 (10)
C5	0.0342 (12)	0.0283 (12)	0.0230 (12)	0.0015 (10)	−0.0020 (9)	−0.0070 (10)
C6	0.0281 (11)	0.0275 (12)	0.0175 (11)	0.0092 (9)	−0.0018 (8)	−0.0033 (9)
C7	0.0564 (19)	0.076 (2)	0.0250 (15)	−0.0218 (17)	0.0066 (13)	0.0033 (15)
C8	0.0327 (12)	0.0255 (12)	0.0192 (11)	0.0047 (9)	−0.0004 (9)	−0.0039 (9)
C9	0.0391 (14)	0.0418 (15)	0.0263 (13)	0.0132 (12)	0.0014 (10)	0.0018 (11)
C10	0.060 (2)	0.104 (3)	0.0233 (15)	0.040 (2)	−0.0041 (14)	0.0002 (17)
C11	0.0513 (18)	0.0549 (19)	0.0393 (17)	0.0250 (15)	0.0012 (13)	0.0036 (15)
C12	0.050 (2)	0.100 (4)	0.079 (3)	0.016 (2)	0.004 (2)	0.004 (3)

Geometric parameters (Å, º) top

Br—C1	1.894 (3)	C5—H5A	0.9500
O1—C4	1.359 (3)	C6—C8	1.506 (3)
O1—C7	1.431 (4)	C7—H7A	0.9800
O2—C8	1.228 (3)	C7—H7B	0.9800
N1—C8	1.338 (3)	C7—H7C	0.9800
N1—N2	1.394 (3)	C9—C10	1.507 (4)
N1—H1A	0.8800	C9—C11	1.508 (4)
N2—C9	1.266 (4)	C10—H10A	0.9800
C1—C2	1.382 (4)	C10—H10B	0.9800
C1—C6	1.383 (3)	C10—H10C	0.9800
C2—C3	1.386 (4)	C11—C12	1.482 (6)
C2—H2A	0.9500	C11—H11A	0.9900
C3—C4	1.383 (4)	C11—H11B	0.9900
C3—H3A	0.9500	C12—H12A	0.9800
C4—C5	1.393 (4)	C12—H12B	0.9800
C5—C6	1.376 (4)	C12—H12C	0.9800

C4—O1—C7	117.4 (2)	H7A—C7—H7C	109.5
C8—N1—N2	119.4 (2)	H7B—C7—H7C	109.5
C8—N1—H1A	120.3	O2—C8—N1	121.9 (2)
N2—N1—H1A	120.3	O2—C8—C6	120.0 (2)
C9—N2—N1	117.5 (2)	N1—C8—C6	118.2 (2)
C2—C1—C6	120.6 (2)	N2—C9—C10	126.3 (3)
C2—C1—Br	118.8 (2)	N2—C9—C11	116.0 (3)
C6—C1—Br	120.59 (19)	C10—C9—C11	117.6 (3)
C1—C2—C3	120.3 (2)	C9—C10—H10A	109.5
C1—C2—H2A	119.9	C9—C10—H10B	109.5
C3—C2—H2A	119.9	H10A—C10—H10B	109.5
C4—C3—C2	119.4 (2)	C9—C10—H10C	109.5
C4—C3—H3A	120.3	H10A—C10—H10C	109.5
C2—C3—H3A	120.3	H10B—C10—H10C	109.5
O1—C4—C3	124.8 (2)	C12—C11—C9	113.8 (3)
O1—C4—C5	115.4 (2)	C12—C11—H11A	108.8
C3—C4—C5	119.8 (2)	C9—C11—H11A	108.8
C6—C5—C4	120.8 (2)	C12—C11—H11B	108.8
C6—C5—H5A	119.6	C9—C11—H11B	108.8
C4—C5—H5A	119.6	H11A—C11—H11B	107.7
C5—C6—C1	119.1 (2)	C11—C12—H12A	109.5
C5—C6—C8	118.1 (2)	C11—C12—H12B	109.5
C1—C6—C8	122.7 (2)	H12A—C12—H12B	109.5
O1—C7—H7A	109.5	C11—C12—H12C	109.5
O1—C7—H7B	109.5	H12A—C12—H12C	109.5
H7A—C7—H7B	109.5	H12B—C12—H12C	109.5
O1—C7—H7C	109.5

C8—N1—N2—C9	179.2 (3)	Br—C1—C6—C5	179.97 (19)
C6—C1—C2—C3	0.8 (4)	C2—C1—C6—C8	175.6 (2)
Br—C1—C2—C3	−179.4 (2)	Br—C1—C6—C8	−4.2 (3)
C1—C2—C3—C4	−0.2 (4)	N2—N1—C8—O2	179.0 (3)
C7—O1—C4—C3	−2.5 (4)	N2—N1—C8—C6	−2.5 (4)
C7—O1—C4—C5	177.0 (3)	C5—C6—C8—O2	74.8 (3)
C2—C3—C4—O1	178.4 (3)	C1—C6—C8—O2	−101.1 (3)
C2—C3—C4—C5	−1.0 (4)	C5—C6—C8—N1	−103.7 (3)
O1—C4—C5—C6	−177.9 (2)	C1—C6—C8—N1	80.4 (3)
C3—C4—C5—C6	1.6 (4)	N1—N2—C9—C10	−3.0 (5)
C4—C5—C6—C1	−0.9 (4)	N1—N2—C9—C11	177.4 (3)
C4—C5—C6—C8	−177.0 (2)	N2—C9—C11—C12	122.5 (4)
C2—C1—C6—C5	−0.3 (4)	C10—C9—C11—C12	−57.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O2ⁱ	0.98	2.60	3.561 (4)	166
C10—H10A···Brⁱⁱ	0.98	3.07	3.949 (5)	151
C10—H10A···O2ⁱⁱⁱ	0.98	2.55	3.231 (4)	127
C11—H11A···O1^iv	0.99	2.55	3.373 (4)	141
N1—H1A···O2ⁱⁱⁱ	0.88	2.07	2.932 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅BrN₂O₂
M_r	299.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	8.0942 (1), 14.2475 (2), 11.2974 (2)
β (°)	91.1519 (13)
V (Å³)	1302.58 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	4.25
Crystal size (mm)	0.56 × 0.47 × 0.35

Data collection
Diffractometer	Oxford Diffraction Gemini R CCD
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.452, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7962, 2577, 2484
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.122, 1.07
No. of reflections	2577
No. of parameters	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −1.07

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), 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
C7—H7B···O2ⁱ	0.98	2.60	3.561 (4)	166.4
C10—H10A···Brⁱⁱ	0.98	3.07	3.949 (5)	150.7
C10—H10A···O2ⁱⁱⁱ	0.98	2.55	3.231 (4)	126.8
C11—H11A···O1^iv	0.99	2.55	3.373 (4)	140.5
N1—H1A···O2ⁱⁱⁱ	0.88	2.07	2.932 (3)	165.2

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

Acknowledgements

LPS thanks the University of Mysore for use of their research facilities under the MPhil programme in Chemistry for the year 2008–2009. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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