4-Amino-N-(6-chloro-5-methoxy­pyrimidin-4-yl)benzene­sulfonamide

Fun, H.-K.; Goh, J.H.; Chidan Kumar, C.S.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536810001121

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Pages o372-o373

https://doi.org/10.1107/S1600536810001121

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4-Amino-N-(6-chloro-5-methoxypyrimidin-4-yl)benzenesulfonamide

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § C. S. Chidan Kumar,^b H. S. Yathirajan ^b and B. Narayana ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 5 January 2010; accepted 9 January 2010; online 16 January 2010)

In the title compound, C₁₁H₁₁ClN₄O₃S, the S atom is bonded in a distorted tetrahedral geometry, by two O atoms, a C atom of the benzene ring and an amino N atom. The essentially planar pyrimidine ring [maximum deviation = 0.020 (1) Å] forms a dihedral angle of 87.57 (5)° with the benzene ring. In the crystal structure, pairs of molecules are linked by intermolecular N—H⋯O hydrogen bonds to generate centrosymmetric R₂²(8) ring motifs. In addition, molecules are linked into a three-dimensional extended network by intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds.

Related literature

For general background to and applications of the title compound, see: Amir et al. (2007 ); Calabresi et al. (1975 ); El-Hashash et al. (1993 ); Nagaraja et al. (2003 ); Townsend & Drach (2002 ). For a related structure, see: Chohan et al. (2008 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₁ClN₄O₃S
M_r = 314.75
Monoclinic, P 2₁ /c
a = 12.8792 (6) Å
b = 13.3557 (6) Å
c = 8.0867 (4) Å
β = 102.396 (1)°
V = 1358.57 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 100 K
0.44 × 0.33 × 0.12 mm

Data collection

Bruker SMART APEX DUO area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.829, T_max = 0.950
20122 measured reflections
4863 independent reflections
4292 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.089
S = 1.04
4863 reflections
225 parameters
All H-atom parameters refined
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N4ⁱ	0.875 (19)	2.616 (18)	3.4230 (14)	153.8 (15)
N1—H2N1⋯O1ⁱⁱ	0.882 (18)	2.533 (19)	3.3274 (13)	150.2 (15)
N2—H1N2⋯O2ⁱⁱⁱ	0.880 (18)	2.031 (18)	2.8866 (12)	163.7 (16)
C4—H4A⋯O1ⁱⁱ	0.944 (16)	2.460 (16)	3.2603 (13)	142.5 (13)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ ; (ii) x, y, z+1; (iii) -x, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810001121/lh2975sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001121/lh2975Isup2.hkl

checkCIF report

Comment top

The importance of pyrimidines and analogous compounds in pharmaceutical and biological fields is well known (Townsend et al., 2002). Some substituted pyrimidines and their derivaties have been reported to possess anti-microbial and anti-fungal activities (El-Hashash et al., 1993). Pyrimidines have incidental anti-viral activity against herpes and vaccinia infections (Calabresi et al., 1975). A review on pyrimidines as anti-inflammatory agent is described by Amir et al. (2007). Sulfonamides are an important class of anti-bacterial drugs used in medicine and veterinary practice. Sulfa drugs are widely used in the treatment of infections, especially for patients intolerant to antibiotics. The vast commercial success of these medicinal agents has made the chemistry of sulfonamides to become a major area of research and an important branch of commercial importance in pharmaceutical sciences (Nagaraja et al., 2003). In view of the importance of the title compound possessing potential anti-bacterial properties, its crystal structure is reported herein.

In the title sulfonamide compound (Fig. 1), the geometry around the S1 atom is a distorted tetrahedron, comprising of atoms O1 and O2 of the sulfonyl group, C6 atom of benzene ring and the amino atom N2. The O1–S1–O2 and O2–S1–N2 angles are 119.20 (5) and 102.20 (4)°, respectively, and the C6–S1–N2–C7 torsion angle is -68.95 (9)°. The pyrimidine ring is essentially planar, with r.m.s. deviation of -0.020 (1) Å, and is almost perpendicular to the benzene ring (C1-C6), as indicated by the dihedral angle of 87.57 (5)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a related structure (Chohan et al., 2008). In the crystal structure, pairs of intermolecular N2—H1N2···O2ⁱⁱⁱ hydrogen bonds (see Table 1 for symmetry code) generate R²₂(8) ring motifs (Bernstein et al., 1995). Neighbouring molecules are linked into a three-dimensional extended network by intermolecular N1—H1N1···N4, N1—H2N1···O1 and C4—H4A···O1 hydrogen bonds (Fig. 2).

Related literature top

For general background to and applications of the title compound, see: Amir et al. (2007); Calabresi et al. (1975); El-Hashash et al. (1993); Nagaraja et al. (2003); Townsend et al. (2002). For a related structure, see: Chohan et al. (2008). For details of hydrogen-bond motifs, see : Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem, Bangalore, India. The compound was used without further purification. Single crystals of good quality were obtained from slow evaporation of an acetonitrile solution. M.p. 447–450 K.

Structure description top

For general background to and applications of the title compound, see: Amir et al. (2007); Calabresi et al. (1975); El-Hashash et al. (1993); Nagaraja et al. (2003); Townsend et al. (2002). For a related structure, see: Chohan et al. (2008). For details of hydrogen-bond motifs, see : Bernstein et al. (1995). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
	Fig. 2. Part of the crystal structure of the title compound, viewed along the c axis, showing a three-dimensional extended network. H atoms not involved in intermolecular hydrogen bonds (dashed lines) have been omitted for clarity.

4-Amino-N-(6-chloro-5-methoxypyrimidin-4-yl)benzenesulfonamide top

Crystal data top

C₁₁H₁₁ClN₄O₃S	F(000) = 648
M_r = 314.75	D_x = 1.539 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9451 reflections
a = 12.8792 (6) Å	θ = 3.1–35.0°
b = 13.3557 (6) Å	µ = 0.45 mm⁻¹
c = 8.0867 (4) Å	T = 100 K
β = 102.396 (1)°	Plate, colourless
V = 1358.57 (11) Å³	0.44 × 0.33 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX DUO area-detector diffractometer	4863 independent reflections
Radiation source: fine-focus sealed tube	4292 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 32.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→18
T_min = 0.829, T_max = 0.950	k = −20→20
20122 measured reflections	l = −11→12

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	All H-atom parameters refined
S = 1.04	w = 1/[σ²(F_o²) + (0.0475P)² + 0.4528P] where P = (F_o² + 2F_c²)/3
4863 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₁H₁₁ClN₄O₃S	V = 1358.57 (11) Å³
M_r = 314.75	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8792 (6) Å	µ = 0.45 mm⁻¹
b = 13.3557 (6) Å	T = 100 K
c = 8.0867 (4) Å	0.44 × 0.33 × 0.12 mm
β = 102.396 (1)°

Data collection top

Bruker SMART APEX DUO area-detector diffractometer	4863 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4292 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.950	R_int = 0.026
20122 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.089	All H-atom parameters refined
S = 1.04	Δρ_max = 0.53 e Å⁻³
4863 reflections	Δρ_min = −0.37 e Å⁻³
225 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.32221 (2)	0.130087 (19)	0.89383 (4)	0.02300 (7)
S1	0.150384 (18)	0.591224 (17)	0.98106 (3)	0.01312 (6)
O1	0.19845 (6)	0.64388 (6)	0.86316 (9)	0.01714 (14)
O2	0.03978 (6)	0.60773 (6)	0.97922 (10)	0.01793 (14)
O3	0.15020 (6)	0.26617 (6)	0.97198 (9)	0.01711 (14)
N1	0.40417 (8)	0.62924 (7)	1.67597 (11)	0.02030 (18)
N2	0.15327 (7)	0.46898 (6)	0.94120 (11)	0.01577 (15)
N3	0.32756 (7)	0.46232 (7)	0.89578 (12)	0.01792 (16)
N4	0.40819 (7)	0.30443 (7)	0.86117 (13)	0.01997 (17)
C1	0.32974 (8)	0.63720 (7)	1.21150 (12)	0.01551 (17)
C2	0.38928 (8)	0.64543 (8)	1.37493 (13)	0.01691 (17)
C3	0.34401 (8)	0.62413 (7)	1.51452 (12)	0.01546 (17)
C4	0.23638 (8)	0.59518 (8)	1.48550 (13)	0.01756 (18)
C5	0.17708 (8)	0.58676 (8)	1.32262 (13)	0.01685 (18)
C6	0.22376 (7)	0.60750 (7)	1.18497 (12)	0.01355 (16)
C7	0.24116 (7)	0.41496 (7)	0.92115 (12)	0.01407 (16)
C8	0.23504 (7)	0.30973 (7)	0.92579 (12)	0.01413 (16)
C9	0.32214 (8)	0.25928 (7)	0.89322 (12)	0.01631 (17)
C10	0.40614 (8)	0.40413 (8)	0.86664 (15)	0.0207 (2)
C11	0.07329 (9)	0.21978 (10)	0.83669 (16)	0.0253 (2)
H1A	0.3591 (13)	0.6546 (12)	1.120 (2)	0.025 (4)*
H2A	0.4615 (13)	0.6672 (13)	1.393 (2)	0.027 (4)*
H4A	0.2078 (13)	0.5806 (12)	1.581 (2)	0.027 (4)*
H5A	0.1038 (13)	0.5624 (12)	1.303 (2)	0.026 (4)*
H10A	0.4693 (14)	0.4379 (13)	0.847 (2)	0.030 (4)*
H11A	0.0146 (14)	0.2042 (14)	0.883 (2)	0.035 (4)*
H11B	0.0532 (14)	0.2688 (14)	0.743 (2)	0.038 (5)*
H11C	0.0991 (15)	0.1654 (16)	0.795 (2)	0.043 (5)*
H1N1	0.4646 (14)	0.6617 (14)	1.695 (2)	0.033 (4)*
H2N1	0.3696 (15)	0.6271 (14)	1.759 (2)	0.034 (5)*
H1N2	0.1012 (14)	0.4342 (13)	0.968 (2)	0.030 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02251 (13)	0.01320 (11)	0.03324 (15)	0.00115 (8)	0.00591 (10)	−0.00126 (9)
S1	0.01184 (10)	0.01368 (11)	0.01457 (11)	0.00149 (7)	0.00442 (8)	0.00027 (7)
O1	0.0191 (3)	0.0179 (3)	0.0156 (3)	0.0009 (3)	0.0064 (3)	0.0026 (2)
O2	0.0121 (3)	0.0195 (3)	0.0228 (3)	0.0032 (2)	0.0050 (3)	0.0005 (3)
O3	0.0161 (3)	0.0188 (3)	0.0177 (3)	−0.0056 (3)	0.0064 (3)	−0.0027 (3)
N1	0.0241 (4)	0.0228 (4)	0.0140 (4)	−0.0020 (3)	0.0041 (3)	−0.0002 (3)
N2	0.0129 (3)	0.0139 (3)	0.0220 (4)	−0.0005 (3)	0.0071 (3)	−0.0028 (3)
N3	0.0143 (4)	0.0154 (4)	0.0260 (4)	0.0000 (3)	0.0085 (3)	−0.0005 (3)
N4	0.0161 (4)	0.0172 (4)	0.0285 (4)	0.0019 (3)	0.0091 (3)	0.0003 (3)
C1	0.0155 (4)	0.0164 (4)	0.0160 (4)	−0.0008 (3)	0.0063 (3)	0.0003 (3)
C2	0.0159 (4)	0.0189 (4)	0.0167 (4)	−0.0015 (3)	0.0053 (3)	0.0000 (3)
C3	0.0191 (4)	0.0130 (4)	0.0148 (4)	0.0011 (3)	0.0049 (3)	−0.0002 (3)
C4	0.0202 (4)	0.0185 (4)	0.0161 (4)	−0.0004 (3)	0.0087 (3)	0.0009 (3)
C5	0.0157 (4)	0.0188 (4)	0.0178 (4)	−0.0007 (3)	0.0076 (3)	0.0008 (3)
C6	0.0135 (4)	0.0136 (4)	0.0145 (4)	0.0006 (3)	0.0049 (3)	0.0000 (3)
C7	0.0123 (4)	0.0149 (4)	0.0154 (4)	0.0003 (3)	0.0041 (3)	−0.0017 (3)
C8	0.0137 (4)	0.0148 (4)	0.0144 (4)	−0.0013 (3)	0.0041 (3)	−0.0010 (3)
C9	0.0167 (4)	0.0135 (4)	0.0189 (4)	0.0011 (3)	0.0042 (3)	−0.0011 (3)
C10	0.0153 (4)	0.0180 (4)	0.0313 (5)	0.0004 (3)	0.0103 (4)	−0.0002 (4)
C11	0.0196 (5)	0.0299 (6)	0.0268 (5)	−0.0086 (4)	0.0058 (4)	−0.0109 (4)

Geometric parameters (Å, º) top

Cl1—C9	1.7255 (10)	C1—C2	1.3826 (14)
S1—O1	1.4283 (7)	C1—C6	1.3932 (13)
S1—O2	1.4383 (7)	C1—H1A	0.931 (16)
S1—N2	1.6662 (9)	C2—C3	1.4063 (13)
S1—C6	1.7292 (10)	C2—H2A	0.955 (17)
O3—C8	1.3590 (11)	C3—C4	1.4094 (14)
O3—C11	1.4480 (13)	C4—C5	1.3781 (15)
N1—C3	1.3694 (13)	C4—H4A	0.941 (17)
N1—H1N1	0.875 (18)	C5—C6	1.4016 (13)
N1—H2N1	0.879 (19)	C5—H5A	0.979 (16)
N2—C7	1.3809 (12)	C7—C8	1.4085 (14)
N2—H1N2	0.880 (18)	C8—C9	1.3816 (13)
N3—C7	1.3336 (12)	C10—H10A	0.973 (17)
N3—C10	1.3364 (13)	C11—H11A	0.938 (18)
N4—C10	1.3328 (14)	C11—H11B	0.991 (19)
N4—C9	1.3351 (13)	C11—H11C	0.90 (2)

O1—S1—O2	119.20 (5)	C3—C4—H4A	117.7 (10)
O1—S1—N2	108.81 (4)	C4—C5—C6	119.92 (9)
O2—S1—N2	102.20 (4)	C4—C5—H5A	119.9 (10)
O1—S1—C6	110.38 (5)	C6—C5—H5A	120.1 (10)
O2—S1—C6	109.14 (5)	C1—C6—C5	120.47 (9)
N2—S1—C6	106.10 (5)	C1—C6—S1	119.96 (7)
C8—O3—C11	115.81 (8)	C5—C6—S1	119.52 (8)
C3—N1—H1N1	119.3 (12)	N3—C7—N2	120.16 (9)
C3—N1—H2N1	116.6 (12)	N3—C7—C8	122.05 (9)
H1N1—N1—H2N1	117.5 (17)	N2—C7—C8	117.78 (8)
C7—N2—S1	125.98 (7)	O3—C8—C9	125.25 (9)
C7—N2—H1N2	116.1 (11)	O3—C8—C7	119.17 (8)
S1—N2—H1N2	114.8 (11)	C9—C8—C7	115.41 (9)
C7—N3—C10	116.09 (9)	N4—C9—C8	123.96 (9)
C10—N4—C9	114.94 (9)	N4—C9—Cl1	116.89 (7)
C2—C1—C6	119.60 (9)	C8—C9—Cl1	119.15 (8)
C2—C1—H1A	120.2 (10)	N4—C10—N3	127.44 (10)
C6—C1—H1A	120.1 (10)	N4—C10—H10A	115.8 (10)
C1—C2—C3	120.71 (9)	N3—C10—H10A	116.8 (10)
C1—C2—H2A	119.7 (10)	O3—C11—H11A	105.7 (11)
C3—C2—H2A	119.6 (10)	O3—C11—H11B	108.5 (11)
N1—C3—C2	120.53 (9)	H11A—C11—H11B	110.6 (15)
N1—C3—C4	120.49 (9)	O3—C11—H11C	112.6 (12)
C2—C3—C4	118.96 (9)	H11A—C11—H11C	111.6 (17)
C5—C4—C3	120.34 (9)	H11B—C11—H11C	107.8 (16)
C5—C4—H4A	122.0 (10)

O1—S1—N2—C7	49.81 (10)	C10—N3—C7—N2	−175.76 (10)
O2—S1—N2—C7	176.75 (8)	C10—N3—C7—C8	3.19 (15)
C6—S1—N2—C7	−68.95 (9)	S1—N2—C7—N3	−14.89 (14)
C6—C1—C2—C3	0.01 (15)	S1—N2—C7—C8	166.11 (7)
C1—C2—C3—N1	177.89 (10)	C11—O3—C8—C9	−78.05 (13)
C1—C2—C3—C4	−0.66 (15)	C11—O3—C8—C7	106.84 (11)
N1—C3—C4—C5	−177.74 (10)	N3—C7—C8—O3	172.23 (9)
C2—C3—C4—C5	0.80 (15)	N2—C7—C8—O3	−8.80 (13)
C3—C4—C5—C6	−0.30 (15)	N3—C7—C8—C9	−3.36 (14)
C2—C1—C6—C5	0.51 (15)	N2—C7—C8—C9	175.62 (9)
C2—C1—C6—S1	−176.93 (8)	C10—N4—C9—C8	1.60 (15)
C4—C5—C6—C1	−0.37 (15)	C10—N4—C9—Cl1	−178.19 (8)
C4—C5—C6—S1	177.08 (8)	O3—C8—C9—N4	−174.46 (10)
O1—S1—C6—C1	−20.24 (9)	C7—C8—C9—N4	0.82 (14)
O2—S1—C6—C1	−153.06 (8)	O3—C8—C9—Cl1	5.32 (14)
N2—S1—C6—C1	97.49 (8)	C7—C8—C9—Cl1	−179.40 (7)
O1—S1—C6—C5	162.29 (8)	C9—N4—C10—N3	−1.89 (18)
O2—S1—C6—C5	29.47 (9)	C7—N3—C10—N4	−0.47 (18)
N2—S1—C6—C5	−79.98 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N4ⁱ	0.875 (19)	2.616 (18)	3.4230 (14)	153.8 (15)
N1—H2N1···O1ⁱⁱ	0.882 (18)	2.533 (19)	3.3274 (13)	150.2 (15)
N2—H1N2···O2ⁱⁱⁱ	0.880 (18)	2.031 (18)	2.8866 (12)	163.7 (16)
C4—H4A···O1ⁱⁱ	0.944 (16)	2.460 (16)	3.2603 (13)	142.5 (13)

Symmetry codes: (i) −x+1, y+1/2, −z+5/2; (ii) x, y, z+1; (iii) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁ClN₄O₃S
M_r	314.75
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.8792 (6), 13.3557 (6), 8.0867 (4)
β (°)	102.396 (1)
V (Å³)	1358.57 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.44 × 0.33 × 0.12

Data collection
Diffractometer	Bruker SMART APEX DUO area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.829, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	20122, 4863, 4292
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.089, 1.04
No. of reflections	4863
No. of parameters	225
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.37

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N4ⁱ	0.875 (19)	2.616 (18)	3.4230 (14)	153.8 (15)
N1—H2N1···O1ⁱⁱ	0.882 (18)	2.533 (19)	3.3274 (13)	150.2 (15)
N2—H1N2···O2ⁱⁱⁱ	0.880 (18)	2.031 (18)	2.8866 (12)	163.7 (16)
C4—H4A···O1ⁱⁱ	0.944 (16)	2.460 (16)	3.2603 (13)	142.5 (13)

Symmetry codes: (i) −x+1, y+1/2, −z+5/2; (ii) x, y, z+1; (iii) −x, −y+1, −z+2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. CSC thanks the University of Mysore for research facilities.

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