3-[(Methyl­carbamo­yl)amino]-1H-isoindolium chloride

Maliha, B.; Tariq, M.I.; Tahir, M.N.; Hussain, I.; Siddiqui, H.L.

doi:10.1107/S1600536809003699

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o448

doi:10.1107/S1600536809003699

Open

access

3-[(Methylcarbamoyl)amino]-1H-isoindolium chloride

Bushra Maliha,^a Muhammad Ilyas Tariq,^b M. Nawaz Tahir,^c ^* Ishtiaq Hussain ^d and Hamid Latif Siddiqui ^a

^aUniversity of the Punjab, Institute of Chemistry, Lahore 54590, Pakistan, ^bUniversity of Sargodha, Department of Chemistry, Sargodha, Pakistan, ^cUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^dUniversity of the Punjab, Institute of Chemistry, Lahore-54590, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 16 December 2008; accepted 29 January 2009; online 4 February 2009)

The title compound, C₁₀H₁₂N₃O⁺·Cl⁻, is a derivative of o-phthaldehyde and methylthiourea. The molecules form dimers through intra- and intermolecular N—H⋯O hydrogen bonds. The dimers are further linked into chains through one C—H⋯Cl and two N—H⋯Cl hydrogen bonds.

Related literature

For applications of iminium salts, see: Page et al. (2008 ); Skalkos et al. (1994 ) Tariq et al. (2008 ). For the formation of derivatives of o-phthaldehyde with different ureas, see: Maliha, Tariq, Tahir, Hussain & Ali (2009 ); Maliha, Tariq, Tahir, Hussain & Siddiqui (2009 ); Maliha et al. (2008 ). For a related structure, see: Arfan et al. (2008 ).

Experimental

Crystal data

C₁₀H₁₂N₃O⁺·Cl⁻
M_r = 225.68
Triclinic, $[P \overline 1]$
a = 7.1171 (5) Å
b = 7.7900 (6) Å
c = 10.3033 (8) Å
α = 89.484 (3)°
β = 69.997 (2)°
γ = 74.613 (4)°
V = 515.43 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 (2) K
0.30 × 0.10 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.982, T_max = 0.989
8853 measured reflections
2369 independent reflections
2210 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.101
S = 1.01
2369 reflections
146 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.81 (2)	2.22 (2)	2.7097 (16)	119.9 (18)
N1—H1N⋯O1ⁱ	0.81 (2)	2.15 (2)	2.8760 (17)	150 (2)
N2—H2N⋯Cl1ⁱⁱ	0.90 (2)	2.23 (2)	3.0969 (13)	160.5 (18)
N3—H3N⋯Cl1ⁱⁱ	0.86 (2)	2.40 (2)	3.2082 (13)	157.0 (17)
C1—H1B⋯Cl1ⁱⁱⁱ	0.97	2.74	3.6755 (16)	162
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) x+1, y, z.

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, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003699/ez2156sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003699/ez2156Isup2.hkl

checkCIF report

Comment top

Iminium salts are a class of organic compounds acting as reactive intermediates. These are being extensively synthesized and further reacted in an efficient and convenient manner for the preparation of multidrug-resistance reversal agents and pesticides and for metal complexation to form new photosensitizers (Page et al., 2008; Skalkos et al., 1994; Tariq et al., 2008). The present paper relates to the continuation of our studies regarding the formation of derivatives of O-phthaldehyde with different ureas (Maliha et al., 2008; Maliha, Tariq, Tahir, Hussain & Ali, 2009; Maliha, Tariq, Tahir, Hussain & Siddiqui, 2009).

The molecule of the title compound (I; Fig 1), is almost planar. It has three N—H bonds in the asymmetric unit. The N—H of the pyrrole ring forms an intramolecular as well as an intermolecular N–H···O H-bond. The title compound forms a dimer (Fig 2) with a central four membered O···H···O···H unit. The other two N–H groups in the methyl urea moiety are involved in intermolecular H-bonding with the Cl^-. The Cl^- also forms H-bonds with the methylene group of the pyrrole ring. Consequently, the chlorine anion makes three H-bonds. Similar Cl^- bonding behavior has been reported by Arfan et al. (2008). No strong π interactions are observed.

Related literature top

For related literature regarding applications of iminium salts, see: Page et al. (2008); Skalkos et al. (1994) Tariq et al. (2008). For related literature regarding the formation of derivatives of O-phthaldehyde with different ureas, see: Maliha, Tariq, Tahir, Hussain & Ali (2009); Maliha, Tariq, Tahir, Hussain & Siddiqui (2009); Maliha et al. (2008). For a related structure, see: Arfan et al. (2008).

Experimental top

O-phthaldehyde (200 mmol), methylthiourea (200 mmol) and a few drops of 2M HCl were mixed and ground in mortar and pestle. The product obtained was washed sequentially with hexane, ether, ethanol and water. The precipitate was dried and recrystallized from a mixture of methanol:acetone (9:1), by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The title compound (I) with displacement ellipsoids drawn at 50% probability level. Intramolecular H-bonds are indicated by broken lines.
	Fig. 2. The packing of I (PLATON: Spek, 2003) showing the dimers and H-bonds to the chlorine anion. H-bonds are indicated by broken lines.

3-[(Methylcarbamoyl)amino]-1H-isoindolium chloride top

Crystal data top

C₁₀H₁₂N₃O⁺·Cl⁻	Z = 2
M_r = 225.68	F(000) = 236
Triclinic, P1	D_x = 1.454 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1171 (5) Å	Cell parameters from 2369 reflections
b = 7.7900 (6) Å	θ = 3.1–27.5°
c = 10.3033 (8) Å	µ = 0.35 mm⁻¹
α = 89.484 (3)°	T = 296 K
β = 69.997 (2)°	Needle, light yellow
γ = 74.613 (4)°	0.30 × 0.10 × 0.06 mm
V = 515.43 (7) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2369 independent reflections
Radiation source: fine-focus sealed tube	2210 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 7.50 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.982, T_max = 0.989	l = −13→13
8853 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)] = 0.032	Hydrogen site location: mixed
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0646P)² + 0.2853P] where P = (F_o² + 2F_c²)/3
2369 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₀H₁₂N₃O⁺·Cl⁻	γ = 74.613 (4)°
M_r = 225.68	V = 515.43 (7) Å³
Triclinic, P1	Z = 2
a = 7.1171 (5) Å	Mo Kα radiation
b = 7.7900 (6) Å	µ = 0.35 mm⁻¹
c = 10.3033 (8) Å	T = 296 K
α = 89.484 (3)°	0.30 × 0.10 × 0.06 mm
β = 69.997 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2369 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2210 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.989	R_int = 0.020
8853 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.69 e Å⁻³
2369 reflections	Δρ_min = −0.22 e Å⁻³
146 parameters

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 esds 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	0.29475 (16)	0.09740 (13)	0.60677 (11)	0.0195 (3)
N1	0.46180 (18)	0.25619 (17)	0.37719 (12)	0.0161 (3)
N2	0.19866 (18)	0.40058 (16)	0.58681 (12)	0.0155 (3)
N3	0.05849 (19)	0.28726 (17)	0.79177 (13)	0.0177 (3)
C1	0.5740 (2)	0.29979 (19)	0.23859 (15)	0.0175 (4)
C2	0.4836 (2)	0.49861 (19)	0.24873 (15)	0.0165 (4)
C3	0.5278 (2)	0.6215 (2)	0.15233 (15)	0.0201 (4)
C4	0.4209 (2)	0.8007 (2)	0.19298 (17)	0.0222 (4)
C5	0.2750 (2)	0.8576 (2)	0.32626 (17)	0.0214 (4)
C6	0.2298 (2)	0.73562 (19)	0.42329 (15)	0.0183 (4)
C7	0.3359 (2)	0.55629 (19)	0.38103 (14)	0.0149 (4)
C8	0.3263 (2)	0.39698 (18)	0.45638 (14)	0.0147 (3)
C9	0.1900 (2)	0.24711 (19)	0.66151 (14)	0.0155 (3)
C10	0.0312 (3)	0.1475 (2)	0.88541 (15)	0.0218 (4)
Cl1	0.11104 (5)	0.28646 (4)	0.19897 (3)	0.0186 (1)
H1A	0.54729	0.23997	0.16735	0.0210*
H1B	0.72287	0.26795	0.21941	0.0210*
H1N	0.487 (3)	0.156 (3)	0.401 (2)	0.0194*
H2N	0.113 (3)	0.507 (3)	0.631 (2)	0.0186*
H3	0.62547	0.58510	0.06360	0.0242*
H3N	−0.007 (3)	0.397 (3)	0.819 (2)	0.0212*
H4	0.44729	0.88501	0.12976	0.0266*
H5	0.20729	0.97864	0.35036	0.0256*
H6	0.13317	0.77212	0.51234	0.0220*
H10A	0.01212	0.04982	0.83996	0.0327*
H10B	−0.08889	0.19448	0.96722	0.0327*
H10C	0.15238	0.10608	0.91081	0.0327*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0212 (5)	0.0138 (5)	0.0177 (5)	−0.0003 (4)	−0.0033 (4)	0.0024 (4)
N1	0.0167 (5)	0.0144 (6)	0.0145 (6)	−0.0019 (4)	−0.0039 (4)	0.0029 (4)
N2	0.0166 (5)	0.0126 (6)	0.0143 (6)	−0.0020 (4)	−0.0032 (4)	0.0016 (4)
N3	0.0208 (6)	0.0145 (6)	0.0145 (6)	−0.0031 (5)	−0.0036 (5)	0.0021 (4)
C1	0.0162 (6)	0.0182 (7)	0.0149 (6)	−0.0030 (5)	−0.0029 (5)	0.0021 (5)
C2	0.0146 (6)	0.0192 (7)	0.0165 (7)	−0.0058 (5)	−0.0057 (5)	0.0024 (5)
C3	0.0193 (7)	0.0251 (8)	0.0169 (7)	−0.0097 (6)	−0.0049 (5)	0.0049 (6)
C4	0.0251 (7)	0.0221 (8)	0.0249 (7)	−0.0130 (6)	−0.0111 (6)	0.0101 (6)
C5	0.0245 (7)	0.0158 (7)	0.0264 (8)	−0.0074 (6)	−0.0109 (6)	0.0047 (6)
C6	0.0181 (6)	0.0176 (7)	0.0200 (7)	−0.0053 (5)	−0.0074 (5)	0.0016 (5)
C7	0.0142 (6)	0.0160 (6)	0.0164 (7)	−0.0055 (5)	−0.0067 (5)	0.0037 (5)
C8	0.0140 (6)	0.0156 (6)	0.0158 (6)	−0.0040 (5)	−0.0071 (5)	0.0018 (5)
C9	0.0160 (6)	0.0156 (6)	0.0155 (6)	−0.0048 (5)	−0.0062 (5)	0.0033 (5)
C10	0.0280 (7)	0.0197 (7)	0.0156 (7)	−0.0068 (6)	−0.0050 (6)	0.0060 (5)
Cl1	0.0195 (2)	0.0144 (2)	0.0192 (2)	−0.0041 (1)	−0.0040 (1)	0.0002 (1)

Geometric parameters (Å, º) top

O1—C9	1.2234 (17)	C4—C5	1.397 (2)
N1—C1	1.4654 (19)	C5—C6	1.390 (2)
N1—C8	1.3096 (19)	C6—C7	1.392 (2)
N2—C8	1.3356 (18)	C7—C8	1.463 (2)
N2—C9	1.4197 (19)	C1—H1A	0.9700
N3—C9	1.3296 (19)	C1—H1B	0.9700
N3—C10	1.456 (2)	C3—H3	0.9300
N1—H1N	0.81 (2)	C4—H4	0.9300
N2—H2N	0.90 (2)	C5—H5	0.9300
N3—H3N	0.86 (2)	C6—H6	0.9300
C1—C2	1.501 (2)	C10—H10A	0.9600
C2—C3	1.390 (2)	C10—H10B	0.9600
C2—C7	1.395 (2)	C10—H10C	0.9600
C3—C4	1.390 (2)

Cl1···C1	3.4838 (16)	C8···C7^vii	3.457 (2)
Cl1···C2	3.6463 (16)	C9···C3^vii	3.539 (2)
Cl1···C5ⁱ	3.6252 (16)	C9···C6ⁱⁱ	3.358 (2)
Cl1···N2ⁱⁱ	3.0969 (13)	C9···C4^vii	3.513 (2)
Cl1···N3ⁱⁱ	3.2082 (13)	C9···C5ⁱⁱ	3.575 (2)
Cl1···H5ⁱ	2.9100	C10···C4ⁱⁱ	3.500 (3)
Cl1···H1A	2.9300	C10···C5ⁱⁱ	3.579 (3)
Cl1···H1Bⁱⁱⁱ	2.7400	C10···C10^ix	3.283 (2)
Cl1···H2Nⁱⁱ	2.23 (2)	C1···H10B^x	2.9400
Cl1···H3^iv	3.0500	C5···H10Aⁱⁱ	3.0400
Cl1···H3Nⁱⁱ	2.40 (2)	C6···H2N	2.82 (2)
Cl1···H6ⁱⁱ	2.9900	C9···H1N	2.75 (2)
Cl1···H10A^v	3.0400	C10···H10B^ix	3.0600
O1···O1^vi	2.9982 (16)	C10···H10C^ix	3.0700
O1···N1^vi	2.8760 (17)	H1A···Cl1	2.9300
O1···N1	2.7097 (16)	H1B···Cl1^xi	2.7400
O1···H1N^vi	2.15 (2)	H1B···H10B^x	2.4700
O1···H10A	2.6500	H1N···O1^vi	2.15 (2)
O1···H1N	2.22 (2)	H1N···C9	2.75 (2)
N1···O1	2.7097 (16)	H1N···O1	2.22 (2)
N1···O1^vi	2.8760 (17)	H2N···H6	2.4000
N2···Cl1ⁱⁱ	3.0969 (13)	H2N···H3N	2.11 (3)
N3···C5ⁱⁱ	3.436 (2)	H2N···C6	2.82 (2)
N3···C3^vii	3.433 (2)	H2N···Cl1ⁱⁱ	2.23 (2)
N3···Cl1ⁱⁱ	3.2082 (13)	H3···Cl1^iv	3.0500
N2···H6	2.9400	H3N···H2N	2.11 (3)
C1···Cl1	3.4838 (16)	H3N···Cl1ⁱⁱ	2.40 (2)
C2···Cl1	3.6463 (16)	H5···Cl1^viii	2.9100
C3···N3^vii	3.433 (2)	H6···H2N	2.4000
C3···C9^vii	3.539 (2)	H6···N2	2.9400
C4···C9^vii	3.513 (2)	H6···Cl1ⁱⁱ	2.9900
C4···C10ⁱⁱ	3.500 (3)	H10A···O1	2.6500
C5···N3ⁱⁱ	3.436 (2)	H10A···Cl1^v	3.0400
C5···C9ⁱⁱ	3.575 (2)	H10A···C5ⁱⁱ	3.0400
C5···C10ⁱⁱ	3.579 (3)	H10B···C10^ix	3.0600
C5···Cl1^viii	3.6252 (16)	H10B···H1B^xii	2.4700
C6···C9ⁱⁱ	3.358 (2)	H10B···C1^xii	2.9400
C7···C8^vii	3.457 (2)	H10C···C10^ix	3.0700

C1—N1—C8	112.52 (12)	N2—C9—N3	112.47 (12)
C8—N2—C9	124.09 (12)	O1—C9—N2	121.32 (12)
C9—N3—C10	120.48 (13)	O1—C9—N3	126.20 (13)
C8—N1—H1N	125.2 (14)	N1—C1—H1A	111.00
C1—N1—H1N	122.2 (14)	N1—C1—H1B	111.00
C8—N2—H2N	118.4 (13)	C2—C1—H1A	111.00
C9—N2—H2N	117.5 (13)	C2—C1—H1B	111.00
C10—N3—H3N	121.3 (13)	H1A—C1—H1B	109.00
C9—N3—H3N	118.2 (13)	C2—C3—H3	121.00
N1—C1—C2	101.98 (12)	C4—C3—H3	121.00
C1—C2—C3	130.68 (13)	C3—C4—H4	119.00
C3—C2—C7	120.12 (13)	C5—C4—H4	119.00
C1—C2—C7	109.19 (12)	C4—C5—H5	120.00
C2—C3—C4	117.74 (14)	C6—C5—H5	120.00
C3—C4—C5	121.78 (14)	C5—C6—H6	122.00
C4—C5—C6	120.86 (14)	C7—C6—H6	122.00
C5—C6—C7	116.91 (13)	N3—C10—H10A	109.00
C2—C7—C8	106.74 (12)	N3—C10—H10B	109.00
C2—C7—C6	122.59 (13)	N3—C10—H10C	109.00
C6—C7—C8	130.66 (13)	H10A—C10—H10B	109.00
N1—C8—C7	109.54 (12)	H10A—C10—H10C	109.00
N1—C8—N2	126.82 (13)	H10B—C10—H10C	109.00
N2—C8—C7	123.63 (12)

C8—N1—C1—C2	1.26 (17)	C1—C2—C7—C6	177.86 (14)
C1—N1—C8—C7	−1.95 (18)	C1—C2—C7—C8	−1.00 (17)
C1—N1—C8—N2	178.99 (15)	C3—C2—C7—C6	−1.0 (2)
C9—N2—C8—N1	−0.2 (3)	C3—C2—C7—C8	−179.83 (14)
C8—N2—C9—N3	176.55 (15)	C2—C3—C4—C5	0.6 (2)
C9—N2—C8—C7	−179.15 (14)	C3—C4—C5—C6	−0.6 (2)
C8—N2—C9—O1	−3.7 (2)	C4—C5—C6—C7	−0.1 (2)
C10—N3—C9—O1	1.4 (3)	C5—C6—C7—C8	179.48 (16)
C10—N3—C9—N2	−178.92 (15)	C5—C6—C7—C2	0.9 (2)
N1—C1—C2—C3	178.61 (16)	C2—C7—C8—N1	1.83 (18)
N1—C1—C2—C7	−0.06 (17)	C6—C7—C8—N1	−176.90 (16)
C1—C2—C3—C4	−178.36 (16)	C6—C7—C8—N2	2.2 (3)
C7—C2—C3—C4	0.2 (2)	C2—C7—C8—N2	−179.07 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.81 (2)	2.22 (2)	2.7097 (16)	119.9 (18)
N1—H1N···O1^vi	0.81 (2)	2.15 (2)	2.8760 (17)	150 (2)
N2—H2N···Cl1ⁱⁱ	0.90 (2)	2.23 (2)	3.0969 (13)	160.5 (18)
N3—H3N···Cl1ⁱⁱ	0.86 (2)	2.40 (2)	3.2082 (13)	157.0 (17)
C1—H1B···Cl1^xi	0.9700	2.7400	3.6755 (16)	162.00

Symmetry codes: (ii) −x, −y+1, −z+1; (vi) −x+1, −y, −z+1; (xi) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂N₃O⁺·Cl⁻
M_r	225.68
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.1171 (5), 7.7900 (6), 10.3033 (8)
α, β, γ (°)	89.484 (3), 69.997 (2), 74.613 (4)
V (Å³)	515.43 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.30 × 0.10 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.982, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	8853, 2369, 2210
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.101, 1.01
No. of reflections	2369
No. of parameters	146
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.81 (2)	2.22 (2)	2.7097 (16)	119.9 (18)
N1—H1N···O1ⁱ	0.81 (2)	2.15 (2)	2.8760 (17)	150 (2)
N2—H2N···Cl1ⁱⁱ	0.90 (2)	2.23 (2)	3.0969 (13)	160.5 (18)
N3—H3N···Cl1ⁱⁱ	0.86 (2)	2.40 (2)	3.2082 (13)	157.0 (17)
C1—H1B···Cl1ⁱⁱⁱ	0.9700	2.7400	3.6755 (16)	162.00

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, and the University of the Punjab, Lahore, Pakistan, for funding the research.

References

Arfan, M., Tahir, M. N., Khan, R. & Iqbal, M. S. (2008). Acta Cryst. E64, o1505. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Maliha, B., Tariq, M. I., Tahir, M. N., Hussain, I. & Ali, M. (2009). Acta Cryst. E65, o41. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maliha, B., Tariq, M. I., Tahir, M. N., Hussain, I. & Siddiqui, H. L. (2008). Acta Cryst. E64, o786. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maliha, B., Tariq, M. I., Tahir, M. N., Hussain, I. & Siddiqui, H. L. (2009). Acta Cryst. E65, o42–o43. Web of Science CSD CrossRef IUCr Journals Google Scholar
Page, P. C. B., Parker, P., Rassias, G. A., Buckley, B. R. & Bethell, D. (2008). Adv. Synth. Catal. 350, 1867–1874. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Skalkos, D., Hampton, J. A., Keck, R. W., Wagoner, M. & Selman, S. H. (1994). Photochem. Photobiol. 59, 175–181. CrossRef CAS PubMed Web of Science Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tariq, M. I., Siddiqui, H. L., Hussain, I. & Afzal, S. (2008). J. Chem. Soc. Pak. 30, 472–475. CAS Google Scholar