Valyl benzyl ester chloride

Dutkiewicz, G.; Siddaraju, B.P.; Yathirajan, H.S.; Mayekar, A.N.; Kubicki, M.

doi:10.1107/S1600536810000176

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o324

https://doi.org/10.1107/S1600536810000176

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Valyl benzyl ester chloride

Grzegorz Dutkiewicz,^a B. P. Siddaraju,^b H. S. Yathirajan,^c A. N. Mayekar ^d and Maciej Kubicki ^a ^*

^aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland, ^bDepartment of Chemistry, V. V. Puram College of Science, Bangalore 560 004, India, ^cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^dSequent Scientific limited, New Mangalore 575 011, India
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 21 December 2009; accepted 4 January 2010; online 9 January 2010)

In the title compound (systematic name: 1-benzyloxy-3-methyl-1-oxobutan-2-aminium chloride), C₁₂H₁₈NO₂⁺·Cl⁻, the ester group is approximately planar, with a maximum deviation of 0.040 (2) Å from the least-squares plane, and makes a dihedral angle of 28.92 (16)° with the phenyl ring. The crystal structure is organized by N—H⋯Cl hydrogen bonds which join the two components into a chain along the b axis. Pairs of chains arranged antiparallel are interconnected by further N—H⋯Cl hydrogen bonds, forming eight-membered rings. Similar packing modes have been observed in a number of amino acid ester halides with a short unit-cell parameter of ca 5.5 Å along the direction in which the chains run.

Related literature

For valsartan, see: Black et al. (1997 ); Buhlmayer et al. (1994 ). For related structures, see: Bryndal et al. (2006 ); Jaeger et al. (2003 ); Nastopoulos et al. (1987 ). For a description of the Cambridge Structural Database, see: Allen (2002 ). For graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₂H₁₈NO₂⁺·Cl⁻
M_r = 243.72
Monoclinic, P 2₁
a = 9.705 (1) Å
b = 5.406 (1) Å
c = 13.116 (2) Å
β = 96.58 (1)°
V = 683.60 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 295 K
0.4 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.741, T_max = 0.948
2649 measured reflections
2010 independent reflections
1652 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.077
S = 1.06
2010 reflections
159 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 530 Friedel pairs
Flack parameter: 0.02 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.98	2.38	3.301 (3)	157
N2—H2A⋯Cl1ⁱⁱ	1.00 (3)	2.26 (4)	3.201 (3)	156 (2)
N2—H2B⋯Cl1ⁱⁱⁱ	0.90 (3)	2.29 (3)	3.177 (3)	166 (2)
N2—H2C⋯Cl1	0.96 (3)	2.15 (3)	3.101 (2)	172.1 (18)
C4—H4C⋯Cl1^iv	0.96	2.95	3.904 (3)	175
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (iv) x+1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810000176/is2507sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810000176/is2507Isup2.hkl

checkCIF report

Comment top

The title compound (I, Scheme 1), valyl benzyl ester chloride [1-(benzyloxy)-3-methyl-1-oxobutan-2-aminium chloride], is a reactant (Buhlmayer et al., 1994) for the synthesis of valsartan, which belongs to the class of angiotensin II receptor antagonists (Black et al., 1997).

The ester fragment C2/C1/O1/O11/C12 (Fig. 1) is in a good approximation planar, maximum deviation from the least squares plane being 0.040 (2) Å, and it makes a dihedral angle of 28.92 (16)° with the plane of the phenyl ring [planar within 0.009 (3) Å]. The C2—C3 bond is almost perpendicular to the plane of ester group, the torsion angle O11—C1—C2—C3 being -82.2 (3)°.

In the crystal structure, the N—H···Cl hydrogen bonds between the cations and chloride anions join the ionic components into the chains along the b direction (Fig. 2 and Table 1). Within these chains there are additional relatively short and linear C—H···O hydrogen bonds involving the C=O oxygen atom. Using graph-set notation (Bernstein et al., 1995), there are two second-order antiparallel C²₁(4) chains which are interconnected by another hydrogen bonds into two different kinds of third-order hydrogen bonded R⁴₂(8) rings. Similar packing was observed in a number of the amino acid ester halides, and it always was connected with the unit-cell parameter of ca 5.5 Å. In the Cambridge Structural Database (Allen, 2002), there are 25 organic structures of the amino acid ester halides, and 10 of them display similar crystal packing and appropriate unit-cell parameter. For instance, L-tyrosyl methyl ester chloride (Bryndal et al., 2006) crystallizes in P2₁2₁2₁ space group with one of the unit-cell parameters 5.424 (2) Å, valyl methyl ester chloride (Jaeger et al., 2003) - also P2₁2₁2₁, with 5.894 (2) Å, and (S-benzyl-L-cysteine methyl ester hydrochloride (Nastopoulos et al., 1987) - in P2₁ with c = 5.211 (2) Å.

The coordination of Cl ion by three hydrogen bonded N—H groups might be described as a trigonal pyramid with N—H groups at the base and Cl ion in the apex. The H···Cl···H angles are in the range 77–118°, and the sum of these angles is 277°. It might be noted that if these coordination is described as tetragonal, the empty coordination place is taken by relatively strong C—H(methyl)···Cl hydrogen bond (Table 1).

Related literature top

For valsartan, see: Black et al. (1997); Buhlmayer et al. (1994). For related structures, see: Bryndal et al. (2006); Jaeger et al. (2003); Nastopoulos et al. (1987). For a description of the Cambridge Structural Database, see: Allen (2002). For graph-set motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was obtained as a gift sample from Cipla, Bangalore, India. X-ray quality crystals were obtained from slow evaporation of an aqueous solution (m.p. 409–412 K).

Structure description top

For valsartan, see: Black et al. (1997); Buhlmayer et al. (1994). For related structures, see: Bryndal et al. (2006); Jaeger et al. (2003); Nastopoulos et al. (1987). For a description of the Cambridge Structural Database, see: Allen (2002). For graph-set motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Stereochemical Workstation Operation Manual (Siemens, 1989); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic ellipsoid representation of the title compound together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii. Hydrogen bond is shown as dashed line.
	Fig. 2. The hydrogen-bonded structure of the title compound. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) 1 - x, 1/2 + y, -z; (ii) x, 1 + y, z; (iii) 1 - x, -1/2 + y, -z; (iv) x, -1 + y, z; (v) 1 - x, -3/2 + y, -z.]

1-benzyloxy-3-methyl-1-oxobutan-2-aminium chloride top

Crystal data top

C₁₂H₁₈NO₂⁺·Cl⁻	F(000) = 260
M_r = 243.72	D_x = 1.184 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1449 reflections
a = 9.705 (1) Å	θ = 2.1–26.9°
b = 5.406 (1) Å	µ = 0.27 mm⁻¹
c = 13.116 (2) Å	T = 295 K
β = 96.58 (1)°	Prism, colourless
V = 683.60 (18) Å³	0.4 × 0.2 × 0.2 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	2010 independent reflections
Radiation source: Nova (Mo) X-ray Source	1652 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 5.2679 pixels mm^-1	θ_max = 26.9°, θ_min = 2.1°
ω scan	h = −10→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −4→6
T_min = 0.741, T_max = 0.948	l = −15→11
2649 measured reflections

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2010 reflections	Δρ_max = 0.17 e Å⁻³
159 parameters	Δρ_min = −0.24 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 530 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (8)

Crystal data top

C₁₂H₁₈NO₂⁺·Cl⁻	V = 683.60 (18) Å³
M_r = 243.72	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.705 (1) Å	µ = 0.27 mm⁻¹
b = 5.406 (1) Å	T = 295 K
c = 13.116 (2) Å	0.4 × 0.2 × 0.2 mm
β = 96.58 (1)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	2010 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1652 reflections with I > 2σ(I)
T_min = 0.741, T_max = 0.948	R_int = 0.023
2649 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	Δρ_max = 0.17 e Å⁻³
S = 1.06	Δρ_min = −0.24 e Å⁻³
2010 reflections	Absolute structure: Flack (1983), 530 Friedel pairs
159 parameters	Absolute structure parameter: 0.02 (8)
1 restraint

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
C1	0.6929 (3)	1.0154 (5)	0.2145 (2)	0.0492 (6)
O11	0.7115 (2)	0.9397 (3)	0.31112 (13)	0.0744 (6)
C12	0.6987 (5)	1.1297 (7)	0.3890 (2)	0.0963 (12)
H12A	0.6100	1.2132	0.3756	0.116*
H12B	0.7719	1.2516	0.3878	0.116*
C13	0.7099 (4)	1.0030 (7)	0.4919 (2)	0.0766 (10)
C14	0.6351 (4)	1.0998 (9)	0.5647 (2)	0.1010 (13)
H14	0.5791	1.2380	0.5506	0.121*
C15	0.6452 (6)	0.9849 (14)	0.6612 (3)	0.128 (2)
H15	0.5947	1.0479	0.7114	0.154*
C16	0.7258 (7)	0.7875 (13)	0.6824 (4)	0.137 (3)
H16	0.7314	0.7146	0.7469	0.165*
C17	0.7994 (6)	0.6933 (11)	0.6098 (4)	0.1375 (18)
H17	0.8544	0.5539	0.6243	0.165*
C18	0.7931 (5)	0.8035 (8)	0.5143 (3)	0.1053 (14)
H18	0.8459	0.7411	0.4653	0.126*
O1	0.6602 (2)	1.2196 (4)	0.18837 (14)	0.0702 (6)
C2	0.7212 (2)	0.8078 (4)	0.14310 (17)	0.0454 (6)
H2	0.6851	0.6536	0.1691	0.054*
N2	0.6429 (2)	0.8642 (6)	0.04138 (15)	0.0476 (5)
H2A	0.678 (3)	1.021 (7)	0.013 (2)	0.071 (10)*
H2B	0.649 (3)	0.740 (6)	−0.0041 (19)	0.049 (8)*
H2C	0.546 (3)	0.867 (7)	0.0479 (16)	0.064 (7)*
C3	0.8749 (3)	0.7732 (5)	0.1324 (2)	0.0558 (7)
H3	0.8806	0.6464	0.0796	0.067*
C4	0.9422 (3)	1.0029 (7)	0.0953 (3)	0.0886 (11)
H4A	0.9374	1.1335	0.1444	0.124*
H4B	0.8945	1.0526	0.0304	0.124*
H4C	1.0375	0.9688	0.0876	0.124*
C5	0.9560 (3)	0.6756 (7)	0.2299 (3)	0.0844 (10)
H5A	1.0481	0.6321	0.2163	0.118*
H5B	0.9103	0.5321	0.2530	0.118*
H5C	0.9609	0.8010	0.2820	0.118*
Cl1	0.33538 (6)	0.86692 (12)	0.08481 (4)	0.05096 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0545 (16)	0.0364 (15)	0.0597 (15)	−0.0021 (13)	0.0201 (12)	0.0033 (13)
O11	0.1207 (16)	0.0510 (14)	0.0542 (10)	0.0173 (11)	0.0221 (10)	0.0029 (8)
C12	0.171 (4)	0.060 (2)	0.0638 (19)	0.016 (3)	0.040 (2)	−0.0077 (17)
C13	0.107 (3)	0.068 (2)	0.0550 (17)	−0.004 (2)	0.0097 (17)	−0.0008 (16)
C14	0.117 (3)	0.125 (4)	0.062 (2)	−0.008 (3)	0.019 (2)	−0.018 (2)
C15	0.146 (5)	0.179 (6)	0.063 (3)	−0.054 (4)	0.025 (3)	−0.021 (3)
C16	0.181 (6)	0.160 (6)	0.064 (3)	−0.083 (5)	−0.015 (3)	0.021 (3)
C17	0.190 (5)	0.123 (4)	0.089 (3)	0.000 (4)	−0.030 (3)	0.027 (3)
C18	0.143 (4)	0.094 (4)	0.078 (2)	0.013 (3)	0.011 (2)	0.013 (2)
O1	0.1138 (17)	0.0358 (12)	0.0648 (12)	0.0101 (11)	0.0265 (11)	0.0051 (9)
C2	0.0508 (14)	0.0325 (16)	0.0541 (13)	−0.0006 (11)	0.0122 (10)	0.0044 (10)
N2	0.0450 (12)	0.0398 (12)	0.0593 (11)	−0.0043 (17)	0.0117 (9)	−0.0056 (15)
C3	0.0524 (16)	0.0503 (16)	0.0659 (16)	0.0095 (13)	0.0117 (13)	−0.0058 (13)
C4	0.055 (2)	0.090 (3)	0.123 (3)	−0.002 (2)	0.0227 (18)	0.021 (2)
C5	0.066 (2)	0.082 (3)	0.100 (2)	0.0181 (19)	−0.0083 (17)	0.0045 (19)
Cl1	0.0535 (3)	0.0506 (4)	0.0506 (3)	0.0008 (4)	0.0137 (2)	0.0006 (3)

Geometric parameters (Å, º) top

C1—O1	1.188 (3)	C18—H18	0.9300
C1—O11	1.324 (3)	C2—N2	1.489 (3)
C1—C2	1.507 (3)	C2—C3	1.526 (3)
O11—C12	1.464 (4)	C2—H2	0.9800
C12—C13	1.506 (4)	N2—H2A	1.00 (3)
C12—H12A	0.9700	N2—H2B	0.90 (3)
C12—H12B	0.9700	N2—H2C	0.96 (3)
C13—C18	1.359 (5)	C3—C4	1.509 (4)
C13—C14	1.368 (5)	C3—C5	1.518 (4)
C14—C15	1.403 (6)	C3—H3	0.9800
C14—H14	0.9300	C4—H4A	0.9600
C15—C16	1.334 (7)	C4—H4B	0.9600
C15—H15	0.9300	C4—H4C	0.9600
C16—C17	1.353 (8)	C5—H5A	0.9600
C16—H16	0.9300	C5—H5B	0.9600
C17—C18	1.382 (6)	C5—H5C	0.9600
C17—H17	0.9300

O1—C1—O11	124.5 (3)	N2—C2—C3	110.25 (19)
O1—C1—C2	125.0 (2)	C1—C2—C3	113.5 (2)
O11—C1—C2	110.5 (2)	N2—C2—H2	108.6
C1—O11—C12	115.9 (2)	C1—C2—H2	108.6
O11—C12—C13	107.6 (3)	C3—C2—H2	108.6
O11—C12—H12A	110.2	C2—N2—H2A	110.6 (17)
C13—C12—H12A	110.2	C2—N2—H2B	112.0 (16)
O11—C12—H12B	110.2	H2A—N2—H2B	109.2 (19)
C13—C12—H12B	110.2	C2—N2—H2C	109.3 (13)
H12A—C12—H12B	108.5	H2A—N2—H2C	113 (3)
C18—C13—C14	120.1 (4)	H2B—N2—H2C	102 (3)
C18—C13—C12	122.4 (3)	C4—C3—C5	110.8 (3)
C14—C13—C12	117.5 (4)	C4—C3—C2	113.1 (2)
C13—C14—C15	118.2 (5)	C5—C3—C2	112.5 (2)
C13—C14—H14	120.9	C4—C3—H3	106.6
C15—C14—H14	120.9	C5—C3—H3	106.6
C16—C15—C14	121.4 (5)	C2—C3—H3	106.6
C16—C15—H15	119.3	C3—C4—H4A	109.5
C14—C15—H15	119.3	C3—C4—H4B	109.5
C15—C16—C17	119.9 (5)	H4A—C4—H4B	109.5
C15—C16—H16	120.0	C3—C4—H4C	109.5
C17—C16—H16	120.0	H4A—C4—H4C	109.5
C16—C17—C18	120.2 (6)	H4B—C4—H4C	109.5
C16—C17—H17	119.9	C3—C5—H5A	109.5
C18—C17—H17	119.9	C3—C5—H5B	109.5
C13—C18—C17	120.1 (4)	H5A—C5—H5B	109.5
C13—C18—H18	119.9	C3—C5—H5C	109.5
C17—C18—H18	119.9	H5A—C5—H5C	109.5
N2—C2—C1	107.1 (2)	H5B—C5—H5C	109.5

O1—C1—O11—C12	−4.1 (4)	C12—C13—C18—C17	−179.8 (4)
C2—C1—O11—C12	175.1 (3)	C16—C17—C18—C13	−1.8 (7)
C1—O11—C12—C13	174.8 (3)	O1—C1—C2—N2	−25.0 (4)
O11—C12—C13—C18	34.5 (5)	O11—C1—C2—N2	155.9 (2)
O11—C12—C13—C14	−147.1 (3)	O1—C1—C2—C3	96.9 (3)
C18—C13—C14—C15	−1.1 (6)	O11—C1—C2—C3	−82.2 (3)
C12—C13—C14—C15	−179.5 (4)	N2—C2—C3—C4	62.6 (3)
C13—C14—C15—C16	0.4 (6)	C1—C2—C3—C4	−57.6 (3)
C14—C15—C16—C17	−0.3 (7)	N2—C2—C3—C5	−170.9 (3)
C15—C16—C17—C18	1.1 (8)	C1—C2—C3—C5	69.0 (3)
C14—C13—C18—C17	1.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.98	2.38	3.301 (3)	157
N2—H2A···Cl1ⁱⁱ	1.00 (3)	2.26 (4)	3.201 (3)	156 (2)
N2—H2B···Cl1ⁱⁱⁱ	0.90 (3)	2.29 (3)	3.177 (3)	166 (2)
N2—H2C···Cl1	0.96 (3)	2.15 (3)	3.101 (2)	172.1 (18)
C4—H4C···Cl1^iv	0.96	2.95	3.904 (3)	175

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₈NO₂⁺·Cl⁻
M_r	243.72
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	9.705 (1), 5.406 (1), 13.116 (2)
β (°)	96.58 (1)
V (Å³)	683.60 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.4 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.741, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	2649, 2010, 1652
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.636

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.077, 1.06
No. of reflections	2010
No. of parameters	159
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.24
Absolute structure	Flack (1983), 530 Friedel pairs
Absolute structure parameter	0.02 (8)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), Stereochemical Workstation Operation Manual (Siemens, 1989).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.98	2.38	3.301 (3)	157.2
N2—H2A···Cl1ⁱⁱ	1.00 (3)	2.26 (4)	3.201 (3)	156 (2)
N2—H2B···Cl1ⁱⁱⁱ	0.90 (3)	2.29 (3)	3.177 (3)	166 (2)
N2—H2C···Cl1	0.96 (3)	2.15 (3)	3.101 (2)	172.1 (18)
C4—H4C···Cl1^iv	0.96	2.95	3.904 (3)	174.7

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

Acknowledgements

BPS thanks Cipla, Bangalore for the gift of a sample of the title compound

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