4-(4-Methoxy­phen­yl)piperazin-1-ium chloride

Zia-ur-Rehman; Tahir, M.N.; Danish, M.; Muhammad, N.; Ali, S.

doi:10.1107/S1600536809004280

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o503

doi:10.1107/S1600536809004280

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4-(4-Methoxyphenyl)piperazin-1-ium chloride

Zia-ur-Rehman,^a M. Nawaz Tahir,^b ^* Muhammad Danish,^c Niaz Muhammad ^a and Saqib Ali ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cUniversity of Sargodha, Department of Chemistry, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 2 February 2009; accepted 5 February 2009; online 11 February 2009)

In the title compound, C₁₁H₁₇N₂O⁺·Cl⁻, the dihedral angle between the benzene ring and the basal plane of piperazine ring is 39.20 (8)°. In the crystal, intermolecular N—H⋯Cl hydrogen bonds occur. There is also a C—H⋯π interaction between the benzene rings.

Related literature

The title compound was obtained as a by-product in a continuation of work on the synthesis of tin complexes containing piperazine, see: Zia-ur-Rahman et al. (2006 , 2007 ). For related structures, see: Lu (2007 ); Sadiq-ur-Rehman et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₇N₂O⁺·Cl⁻
M_r = 228.72
Orthorhombic, I b a 2
a = 10.2890 (7) Å
b = 31.5218 (18) Å
c = 7.5909 (5) Å
V = 2461.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 (2) K
0.28 × 0.22 × 0.15 mm

Data collection

Bruker KAPPA APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.922, T_max = 0.950
7605 measured reflections
3073 independent reflections
2327 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.139
S = 1.01
3073 reflections
137 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1076 Friedel pairs
Flack parameter: 0.05 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯Cl1ⁱ	0.90	2.20	3.082 (2)	168
N2—H2B⋯Cl1	0.90	2.24	3.134 (3)	177
C3—H3⋯CgAⁱⁱ	0.93	2.88	3.573 (2)	133
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . CgA is the centroid of the benzene ring.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004280/at2720sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004280/at2720Isup2.hkl

checkCIF report

Comment top

In continuation to synthesizing the tin complexes containing piperazine (Zia-ur-Rahman et al., 2006, 2007), the title compound (I), (Fig 1) has been obtained as a byproduct.

The crystal structures of (II) 4-nitrophenylpiperazinium chloride monohydrate (Lu, 2007) and 4-(2-pyridyl)piperazin-1-ium chloride (Sadiq-ur-Rehman et al., 2007) has been reported. The title compound have a replacement of nitro group in (II) with methoxy at the same position. Due to this change it is observed that (I) does not contain water molecule although the aquas medium was present during crystallization. In the title compound the benzene ring A(C1—C6) is planar along with the methoxy group. The piperazinium is in chair form with the basal plane B(C8—C11) and the N–atoms are at a distance of 0.6680 (37) and -0.6620 (46) Å. The dihedral angle between the groups A and B is 39.20 (8)°. The molecules are linked each other through intra and intermolecular H–bonding (Table 1, Fig 2). There exists a π interaction between the C3–H3 and the centroid of the benzene ring.

Related literature top

For the synthesis of tin complexes containing piperazine, see: Zia-ur-Rahman et al. (2006, 2007). For related structures, see: Lu (2007); Sadiq-ur-Rehman et al. (2007). CgA is the centroid of the benzene ring.

Experimental top

Me₂SnCl₂ (0.24 g, 1.08 mmol) in methanol (30 ml) was added dropwise to 4-(4-methoxyphenyl)piperazinium 4-(4-methoxyphenyl)piperazine-1-carbodithioate (0.5 g, 1.08 mmol) in methanol (30 ml) and the mixture was refluxed for 3 h with constant stirring. The 4-(4-methoxyphenyl)piperazinium chloride thus formed, was filtered off and recrystallized from water-ethanol (1:4) to give colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP drawing of the title compound, with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
	Fig. 2. The partial packing figure (PLATON: Spek, 2009) which shows the dimeric nature of the compound.

4-(4-Methoxyphenyl)piperazin-1-ium chloride top

Crystal data top

C₁₁H₁₇N₂O⁺·Cl⁻	F(000) = 976
M_r = 228.72	D_x = 1.234 Mg m⁻³
Orthorhombic, Iba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2c	Cell parameters from 3073 reflections
a = 10.2890 (7) Å	θ = 1.2–30.5°
b = 31.5218 (18) Å	µ = 0.29 mm⁻¹
c = 7.5909 (5) Å	T = 296 K
V = 2461.9 (3) Å³	Prismatic, colourless
Z = 8	0.28 × 0.22 × 0.15 mm

Data collection top

Bruker KAPPA APEXII CCD diffractometer	3073 independent reflections
Radiation source: fine-focus sealed tube	2327 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
Detector resolution: 7.3 pixels mm^-1	θ_max = 30.5°, θ_min = 1.3°
ω scans	h = −14→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −42→44
T_min = 0.922, T_max = 0.950	l = −5→10
7605 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0883P)² + 0.0737P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.139	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.35 e Å⁻³
3073 reflections	Δρ_min = −0.29 e Å⁻³
137 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0136 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1076 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.05 (9)

Crystal data top

C₁₁H₁₇N₂O⁺·Cl⁻	V = 2461.9 (3) Å³
M_r = 228.72	Z = 8
Orthorhombic, Iba2	Mo Kα radiation
a = 10.2890 (7) Å	µ = 0.29 mm⁻¹
b = 31.5218 (18) Å	T = 296 K
c = 7.5909 (5) Å	0.28 × 0.22 × 0.15 mm

Data collection top

Bruker KAPPA APEXII CCD diffractometer	3073 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2327 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.950	R_int = 0.026
7605 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.139	Δρ_max = 0.35 e Å⁻³
S = 1.01	Δρ_min = −0.29 e Å⁻³
3073 reflections	Absolute structure: Flack (1983), 1076 Friedel pairs
137 parameters	Absolute structure parameter: 0.05 (9)
1 restraint

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.41690 (13)	0.30736 (4)	0.7357 (3)	0.0454 (4)
N1	0.30676 (15)	0.13295 (5)	0.7320 (3)	0.0407 (5)
N2	0.25384 (18)	0.04631 (6)	0.6512 (4)	0.0561 (8)
C1	0.33328 (16)	0.17757 (5)	0.7214 (3)	0.0334 (5)
C2	0.25085 (17)	0.20603 (6)	0.6364 (3)	0.0368 (6)
C3	0.27578 (17)	0.24960 (7)	0.6389 (3)	0.0362 (6)
C4	0.38456 (16)	0.26505 (6)	0.7235 (3)	0.0329 (5)
C5	0.46885 (18)	0.23669 (6)	0.8075 (3)	0.0371 (5)
C6	0.44271 (18)	0.19397 (6)	0.8060 (3)	0.0386 (6)
C7	0.3309 (3)	0.33675 (8)	0.6540 (4)	0.0641 (9)
C8	0.1772 (2)	0.11964 (7)	0.6751 (3)	0.0486 (7)
C9	0.1533 (2)	0.07386 (7)	0.7291 (4)	0.0563 (7)
C10	0.3855 (3)	0.06000 (7)	0.7054 (4)	0.0617 (9)
C11	0.4071 (2)	0.10588 (7)	0.6540 (4)	0.0513 (7)
Cl1	0.24567 (7)	0.04913 (2)	0.23863 (13)	0.0710 (3)
H2	0.17815	0.19587	0.57701	0.0442*
H2A	0.24059	0.01935	0.68585	0.0673*
H2B	0.24770	0.04718	0.53299	0.0673*
H3	0.21888	0.26823	0.58342	0.0435*
H5	0.54265	0.24678	0.86451	0.0446*
H6	0.49937	0.17549	0.86277	0.0464*
H7A	0.36281	0.36507	0.67113	0.0962*
H7B	0.32577	0.33080	0.53014	0.0962*
H7C	0.24605	0.33421	0.70556	0.0962*
H8A	0.11208	0.13783	0.72828	0.0583*
H8B	0.17019	0.12226	0.54811	0.0583*
H9A	0.06804	0.06493	0.68906	0.0675*
H9B	0.15557	0.07151	0.85649	0.0675*
H10A	0.39486	0.05691	0.83195	0.0742*
H10B	0.45021	0.04222	0.64893	0.0742*
H11A	0.40474	0.10852	0.52670	0.0615*
H11B	0.49212	0.11503	0.69420	0.0615*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0468 (7)	0.0384 (7)	0.0510 (9)	−0.0060 (5)	−0.0035 (8)	0.0000 (8)
N1	0.0415 (8)	0.0359 (7)	0.0447 (9)	0.0009 (6)	0.0001 (9)	0.0004 (8)
N2	0.0814 (15)	0.0327 (10)	0.0542 (14)	−0.0018 (8)	−0.0042 (10)	0.0048 (9)
C1	0.0351 (8)	0.0346 (8)	0.0306 (9)	0.0019 (6)	0.0006 (9)	−0.0009 (8)
C2	0.0353 (9)	0.0401 (10)	0.0351 (11)	−0.0007 (7)	−0.0065 (8)	0.0002 (8)
C3	0.0345 (9)	0.0382 (10)	0.0359 (10)	0.0024 (7)	−0.0041 (8)	0.0011 (8)
C4	0.0340 (8)	0.0373 (8)	0.0273 (8)	−0.0021 (6)	0.0038 (8)	−0.0019 (8)
C5	0.0320 (8)	0.0467 (10)	0.0327 (9)	−0.0036 (8)	−0.0052 (8)	−0.0020 (8)
C6	0.0352 (9)	0.0458 (10)	0.0349 (10)	0.0064 (8)	−0.0030 (8)	0.0038 (8)
C7	0.0701 (16)	0.0391 (12)	0.083 (2)	−0.0030 (11)	−0.0173 (15)	0.0059 (12)
C8	0.0468 (11)	0.0391 (11)	0.0599 (16)	−0.0038 (9)	−0.0042 (10)	−0.0035 (9)
C9	0.0571 (12)	0.0463 (11)	0.0654 (15)	−0.0088 (9)	0.0005 (14)	0.0007 (13)
C10	0.0658 (14)	0.0392 (11)	0.080 (2)	0.0088 (10)	0.0024 (14)	0.0063 (12)
C11	0.0502 (12)	0.0381 (10)	0.0655 (15)	0.0066 (9)	0.0077 (11)	0.0001 (10)
Cl1	0.1167 (6)	0.0368 (3)	0.0596 (4)	0.0072 (3)	−0.0038 (4)	−0.0031 (3)

Geometric parameters (Å, º) top

O1—C4	1.378 (2)	C10—C11	1.514 (3)
O1—C7	1.423 (3)	C2—H2	0.9300
N1—C1	1.435 (2)	C3—H3	0.9300
N1—C8	1.463 (3)	C5—H5	0.9300
N1—C11	1.464 (3)	C6—H6	0.9300
N2—C9	1.474 (3)	C7—H7A	0.9600
N2—C10	1.480 (4)	C7—H7B	0.9600
N2—H2A	0.9000	C7—H7C	0.9600
N2—H2B	0.9000	C8—H8A	0.9700
C1—C2	1.393 (3)	C8—H8B	0.9700
C1—C6	1.396 (3)	C9—H9A	0.9700
C2—C3	1.397 (3)	C9—H9B	0.9700
C3—C4	1.379 (3)	C10—H10A	0.9700
C4—C5	1.399 (3)	C10—H10B	0.9700
C5—C6	1.373 (3)	C11—H11A	0.9700
C8—C9	1.520 (3)	C11—H11B	0.9700

Cl1···N2	3.134 (3)	H2···H8A	2.2600
Cl1···N2ⁱ	3.082 (2)	H2···H8B	2.3300
Cl1···H2Aⁱ	2.2000	H2A···Cl1^vi	2.2000
Cl1···H9Bⁱⁱ	3.1300	H2B···H11A	2.5200
Cl1···H2B	2.2400	H2B···Cl1	2.2400
Cl1···H7Aⁱⁱⁱ	2.9700	H2B···H8B	2.5000
O1···H2^iv	2.7700	H3···C5ⁱⁱⁱ	2.8500
O1···H8A^v	2.6500	H3···C7	2.5100
N1···N2	2.852 (3)	H3···H7B	2.2900
N2···N1	2.852 (3)	H3···H7C	2.2900
N2···Cl1	3.134 (3)	H3···C6ⁱⁱⁱ	2.9400
N2···Cl1^vi	3.082 (2)	H3···C5^vii	3.0900
N1···H7B^iv	2.8800	H5···C3^ix	2.8000
C2···C4ⁱⁱⁱ	3.549 (3)	H5···C3^v	2.9500
C3···C5^vii	3.435 (3)	H5···C4^ix	2.8800
C3···C5ⁱⁱⁱ	3.585 (3)	H6···C11	2.8700
C3···C4ⁱⁱⁱ	3.589 (3)	H6···H11B	2.3000
C4···C2^iv	3.549 (3)	H7A···Cl1^iv	2.9700
C4···C3^iv	3.589 (3)	H7B···C3	2.7400
C5···C3^v	3.435 (3)	H7B···C1ⁱⁱⁱ	2.8700
C5···C3^iv	3.585 (3)	H7B···H3	2.2900
C1···H7B^iv	2.8700	H7B···N1ⁱⁱⁱ	2.8800
C2···H8A	2.6700	H7B···H8Aⁱⁱⁱ	2.5800
C2···H8B	2.8500	H7C···H3	2.2900
C3···H5^viii	2.8000	H7C···C3	2.7300
C3···H5^vii	2.9500	H8A···C2	2.6700
C3···H7C	2.7300	H8A···H7B^iv	2.5800
C3···H7B	2.7400	H8A···O1^vii	2.6500
C4···H2^iv	3.0200	H8A···H2	2.2600
C4···H5^viii	2.8800	H8A···C7^vii	3.0500
C5···H3^v	3.0900	H8B···H2B	2.5000
C5···H3^iv	2.8500	H8B···H11A	2.4600
C6···H11B	2.6800	H8B···C2	2.8500
C6···H3^iv	2.9400	H8B···H2	2.3300
C7···H8A^v	3.0500	H9B···Cl1^x	3.1300
C7···H3	2.5100	H9B···H10A	2.5100
C8···H2	2.5200	H10A···H9B	2.5100
C11···H6	2.8700	H11A···H2B	2.5200
H2···C8	2.5200	H11A···H8B	2.4600
H2···C4ⁱⁱⁱ	3.0200	H11B···H6	2.3000
H2···O1ⁱⁱⁱ	2.7700	H11B···C6	2.6800

C4—O1—C7	116.79 (18)	C6—C5—H5	120.00
C1—N1—C8	115.97 (16)	C1—C6—H6	119.00
C1—N1—C11	114.48 (16)	C5—C6—H6	119.00
C8—N1—C11	110.85 (17)	O1—C7—H7A	109.00
C9—N2—C10	111.0 (2)	O1—C7—H7B	109.00
C9—N2—H2B	109.00	O1—C7—H7C	109.00
C10—N2—H2A	109.00	H7A—C7—H7B	109.00
C10—N2—H2B	109.00	H7A—C7—H7C	109.00
H2A—N2—H2B	108.00	H7B—C7—H7C	109.00
C9—N2—H2A	109.00	N1—C8—H8A	110.00
N1—C1—C2	122.78 (16)	N1—C8—H8B	110.00
N1—C1—C6	119.39 (17)	C9—C8—H8A	110.00
C2—C1—C6	117.76 (16)	C9—C8—H8B	110.00
C1—C2—C3	120.99 (17)	H8A—C8—H8B	108.00
C2—C3—C4	120.16 (18)	N2—C9—H9A	110.00
O1—C4—C5	115.99 (17)	N2—C9—H9B	110.00
O1—C4—C3	124.69 (18)	C8—C9—H9A	110.00
C3—C4—C5	119.31 (18)	C8—C9—H9B	110.00
C4—C5—C6	120.09 (18)	H9A—C9—H9B	108.00
C1—C6—C5	121.68 (18)	N2—C10—H10A	110.00
N1—C8—C9	109.88 (17)	N2—C10—H10B	110.00
N2—C9—C8	109.72 (19)	C11—C10—H10A	110.00
N2—C10—C11	110.0 (2)	C11—C10—H10B	110.00
N1—C11—C10	110.4 (2)	H10A—C10—H10B	108.00
C1—C2—H2	119.00	N1—C11—H11A	110.00
C3—C2—H2	120.00	N1—C11—H11B	110.00
C2—C3—H3	120.00	C10—C11—H11A	110.00
C4—C3—H3	120.00	C10—C11—H11B	110.00
C4—C5—H5	120.00	H11A—C11—H11B	108.00

C7—O1—C4—C3	−0.2 (3)	N1—C1—C2—C3	175.8 (2)
C7—O1—C4—C5	−178.8 (2)	C6—C1—C2—C3	−1.2 (3)
C8—N1—C1—C2	−10.2 (3)	N1—C1—C6—C5	−176.6 (2)
C8—N1—C1—C6	166.8 (2)	C2—C1—C6—C5	0.5 (3)
C11—N1—C1—C2	120.9 (2)	C1—C2—C3—C4	1.2 (3)
C11—N1—C1—C6	−62.2 (3)	C2—C3—C4—O1	−179.0 (2)
C1—N1—C8—C9	−168.1 (2)	C2—C3—C4—C5	−0.4 (3)
C11—N1—C8—C9	59.1 (3)	O1—C4—C5—C6	178.4 (2)
C1—N1—C11—C10	167.9 (2)	C3—C4—C5—C6	−0.3 (3)
C8—N1—C11—C10	−58.6 (3)	C4—C5—C6—C1	0.3 (3)
C10—N2—C9—C8	57.6 (3)	N1—C8—C9—N2	−58.2 (3)
C9—N2—C10—C11	−56.9 (3)	N2—C10—C11—N1	56.8 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^vi	0.90	2.20	3.082 (2)	168
N2—H2B···Cl1	0.90	2.24	3.134 (3)	177
C3—H3···CgAⁱⁱⁱ	0.93	2.88	3.573 (2)	133

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇N₂O⁺·Cl⁻
M_r	228.72
Crystal system, space group	Orthorhombic, Iba2
Temperature (K)	296
a, b, c (Å)	10.2890 (7), 31.5218 (18), 7.5909 (5)
V (Å³)	2461.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.28 × 0.22 × 0.15

Data collection
Diffractometer	Bruker KAPPA APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.922, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	7605, 3073, 2327
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.713

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.139, 1.01
No. of reflections	3073
No. of parameters	137
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.29
Absolute structure	Flack (1983), 1076 Friedel pairs
Absolute structure parameter	0.05 (9)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1ⁱ	0.90	2.20	3.082 (2)	168
N2—H2B···Cl1	0.90	2.24	3.134 (3)	177
C3—H3···CgAⁱⁱ	0.93	2.88	3.573 (2)	133

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

Acknowledgements

The authors acknowledge the the Higher Education Commission, Islamabad, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore.

References

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