N-tert-Butyl-2-(2,6-di­chloro­phen­yl)imidazo[1,2-a]pyrazin-3-amine

Fatima, Z.; Srinivasan, T.; Koorathota, S.; Thennarasu, S.; Velmurugan, D.

doi:10.1107/S1600536813013640

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o949-o950

doi:10.1107/S1600536813013640

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N-tert-Butyl-2-(2,6-dichlorophenyl)imidazo[1,2-a]pyrazin-3-amine

Zeenat Fatima,^a Thothadri Srinivasan,^a Suman Koorathota,^b Sathiah Thennarasu ^b and Devadasan Velmurugan ^a ^*

^aCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and ^bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
^*Correspondence e-mail: shirai2011@gmail.com

(Received 13 May 2013; accepted 17 May 2013; online 25 May 2013)

In the title compound, C₁₆H₁₆Cl₂N₄, the imidazole ring mean plane makes a dihedral angle of 70.01 (1)° with the phenyl ring. The Cl atoms deviate by −0.0472 (6) and 0.0245 (8) Å from the plane of their attached benzene ring. In the crystal, molecules are linked via pairs of C—H⋯N hydrogen bonds, forming inversion dimers.

Related literature

For applications of the pyrazine ring system in drug development, see: Du et al. (2009 ); Dubinina et al. (2006 ); Ellsworth et al. (2007 ); Mukaiyama et al. (2007 ). For background to the fluorescence properties of related compounds, see: Kawai et al. (2001 ); Abdullah (2005 ). For general background to the use of imidazole derivatives as drugs, see: Dooley et al. (1992 ); Jackson et al. (2000 ); Banfi et al. (2006 ). For related structures, see: Ouzidan et al. (2011 ); Nasir et al. (2010 ).

Experimental

Crystal data

C₁₆H₁₆Cl₂N₄
M_r = 335.23
Triclinic, $[P \overline 1]$
a = 8.1482 (4) Å
b = 9.8553 (5) Å
c = 11.5265 (6) Å
α = 93.218 (2)°
β = 99.320 (3)°
γ = 113.026 (2)°
V = 833.31 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.892, T_max = 0.926
12583 measured reflections
3438 independent reflections
2941 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.120
S = 1.05
3438 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N2ⁱ	0.93	2.62	3.500 (3)	158
Symmetry code: (i) -x+2, -y, -z.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); 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, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813013640/su2601sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013640/su2601Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013640/su2601Isup3.cml

checkCIF report

Comment top

The pyrazine ring system is a useful structural element in medicinal chemistry and has found broad applications in drug development such as antiproliferative agents (Dubinina et al., 2006), potent CXCR3 antagonists (Du et al., 2009), CB1 antagonists (Ellsworth et al., 2007) and c-Src inhibitors (Mukaiyama et al., 2007). On-going structural studies of heterocyclic N-containing derivatives (Nasir et al., 2010) are motivated by an investigation of their fluorescence properties (Kawai et al., 2001; Abdullah, 2005). For multidrug-resistant Tuberculosis (Dooley et al., 1992), antifungal and antimycobacterial activity (Banfi et al. 2006) and bactericidal effects (Jackson et al. 2000), the use of imidazole based compounds were reported. In view of the different applications of this class of compounds, we have undertaken a single-crystal structure determination of the title compound.

In the titled compound, Fig.1, the imidazole ring (N2/N3/C3/C5/C6) makes a dihedral angle of 1.06 (9)° with the pyrazine ring (N1/N3/C1-C4), and a dihedral angle of 70.01 (1)° with the phenyl ring (C7-C12). The dihedral angle between the pyrazine ring and the phenyl ring is 69.54 (1)°. The chlorine atoms Cl1 and Cl2 attached to the phenyl ring deviate by -0.0472 (6)Å and 0.0245 (8)Å.

In the crystal, molecules are linked via pairs of C—H···N hydrogen bonds forming inversion dimers (Table 1 and Fig.2).

Related literature top

For applications of the pyrazine ring system in drug development, see: Du et al. (2009); Dubinina et al. (2006); Ellsworth et al. (2007); Mukaiyama et al. (2007). For background to the fluorescence properties of related compounds, see: Kawai et al. (2001); Abdullah (2005). For general background to the use of imidazole derivatives as drugs, see: Dooley et al. (1992); Jackson et al. (2000); Banfi et al. (2006). For related structures, see: Ouzidan et al. (2011); Nasir et al. (2010).

Experimental top

2-aminopyrazine (1.0 mmol) was placed in oven-dried round bottom flask, dissolved in EtOH (5.0 mL) and stirred at room temperature. 2,6-dichlorobenzaldehyde (1.0 mmol), tert-butyl isocyanide (1.0 mmol) and Iodine (2.0 mol%) were added together and the mixture stirred, progress of the reaction was monitored by using TLC, at room temperature for one hour. The reaction mixture was concentrated under reduced pressure and the crude product was partitioned between EtOAc and water. The organic phase was separated, and the residual product in the aqueous phase was extracted with EtOAc (2 × 10 mL). The combined organic extract was dried over anhydrous Na₂SO₄, filtered, concentrated and purified using column chromatography (silica gel 60-120 mesh, elutent: 5% EtOAc in hexane).M.p: 421 - 423 k, IR (KBr, cm^-1): 3353 (NH). After two weeks a colourless crystalline solid separated out. It was washed with a minimum amount of ethanol and then dried in a vacuum oven; a crystal was chosen for X-ray diffraction studies from this sample.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The hydrogen bonds are sown as dashed lines (see Table 1 for details; H-atoms not involved in H-bonds have been excluded for clarity).

N-tert-Butyl-2-(2,6-dichlorophenyl)imidazo[1,2-a]pyrazin-3-amine top

Crystal data top

C₁₆H₁₆Cl₂N₄	Z = 2
M_r = 335.23	F(000) = 348
Triclinic, P1	D_x = 1.336 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1482 (4) Å	Cell parameters from 3438 reflections
b = 9.8553 (5) Å	θ = 1.8–26.5°
c = 11.5265 (6) Å	µ = 0.39 mm⁻¹
α = 93.218 (2)°	T = 293 K
β = 99.320 (3)°	Block, colourless
γ = 113.026 (2)°	0.30 × 0.25 × 0.20 mm
V = 833.31 (7) Å³

Data collection top

Bruker SMART APEXII area-detector diffractometer	3438 independent reflections
Radiation source: fine-focus sealed tube	2941 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 26.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.892, T_max = 0.926	k = −12→12
12583 measured reflections	l = −14→14

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)] = 0.040	H-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0616P)² + 0.252P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3438 reflections	Δρ_max = 0.34 e Å⁻³
203 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (4)

Crystal data top

C₁₆H₁₆Cl₂N₄	γ = 113.026 (2)°
M_r = 335.23	V = 833.31 (7) Å³
Triclinic, P1	Z = 2
a = 8.1482 (4) Å	Mo Kα radiation
b = 9.8553 (5) Å	µ = 0.39 mm⁻¹
c = 11.5265 (6) Å	T = 293 K
α = 93.218 (2)°	0.30 × 0.25 × 0.20 mm
β = 99.320 (3)°

Data collection top

Bruker SMART APEXII area-detector diffractometer	3438 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2941 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.926	R_int = 0.026
12583 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
3438 reflections	Δρ_min = −0.40 e Å⁻³
203 parameters

Special details top

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
C1	0.8515 (3)	0.3445 (2)	−0.14305 (16)	0.0590 (5)
H1	0.8278	0.3957	−0.2044	0.071*
C2	0.8018 (2)	0.3676 (2)	−0.04035 (15)	0.0490 (4)
H2	0.7462	0.4327	−0.0307	0.059*
C3	0.9215 (2)	0.19622 (19)	0.03479 (14)	0.0428 (4)
C4	0.9674 (3)	0.1803 (2)	−0.07708 (15)	0.0573 (5)
H4	1.0238	0.1165	−0.0894	0.069*
C5	0.8067 (2)	0.29067 (17)	0.16413 (13)	0.0374 (3)
C6	0.8760 (2)	0.19427 (17)	0.21161 (13)	0.0386 (3)
C7	0.8730 (2)	0.15258 (17)	0.33280 (13)	0.0412 (4)
C8	0.9765 (2)	0.25222 (19)	0.43377 (14)	0.0466 (4)
C9	0.9642 (3)	0.2172 (2)	0.54712 (16)	0.0618 (5)
H9	1.0343	0.2872	0.6126	0.074*
C10	0.8473 (4)	0.0779 (3)	0.56200 (17)	0.0737 (6)
H10	0.8378	0.0534	0.6381	0.088*
C11	0.7438 (4)	−0.0259 (2)	0.46540 (18)	0.0711 (6)
H11	0.6652	−0.1206	0.4757	0.085*
C12	0.7582 (3)	0.0125 (2)	0.35278 (16)	0.0543 (4)
C13	0.5310 (2)	0.3227 (2)	0.20642 (16)	0.0529 (4)
C14	0.4269 (3)	0.2237 (5)	0.0930 (3)	0.1323 (15)
H14A	0.4406	0.2817	0.0282	0.198*
H14B	0.3004	0.1768	0.0967	0.198*
H14C	0.4727	0.1489	0.0811	0.198*
C15	0.4854 (5)	0.4564 (4)	0.2163 (4)	0.1293 (15)
H15A	0.5521	0.5183	0.2900	0.194*
H15B	0.3572	0.4243	0.2137	0.194*
H15C	0.5178	0.5118	0.1516	0.194*
C16	0.4855 (4)	0.2406 (4)	0.3101 (3)	0.1010 (10)
H16A	0.5025	0.1498	0.3006	0.151*
H16B	0.3611	0.2180	0.3144	0.151*
H16C	0.5639	0.3012	0.3817	0.151*
N1	0.9338 (2)	0.2515 (2)	−0.16355 (13)	0.0635 (4)
N2	0.9474 (2)	0.13643 (16)	0.13275 (12)	0.0466 (3)
N3	0.83689 (17)	0.29093 (14)	0.04973 (11)	0.0386 (3)
N4	0.72957 (19)	0.38082 (15)	0.20777 (13)	0.0471 (3)
H4A	0.7978	0.4719	0.2361	0.057*
Cl1	1.12956 (7)	0.42849 (6)	0.41790 (4)	0.0670 (2)
Cl2	0.62201 (10)	−0.11935 (6)	0.23322 (5)	0.0897 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0591 (11)	0.0737 (12)	0.0376 (9)	0.0192 (9)	0.0069 (8)	0.0206 (8)
C2	0.0468 (9)	0.0563 (10)	0.0433 (9)	0.0191 (8)	0.0079 (7)	0.0192 (7)
C3	0.0458 (8)	0.0510 (9)	0.0335 (8)	0.0213 (7)	0.0092 (6)	0.0038 (6)
C4	0.0675 (12)	0.0724 (12)	0.0367 (9)	0.0316 (10)	0.0160 (8)	0.0033 (8)
C5	0.0377 (7)	0.0415 (7)	0.0325 (7)	0.0145 (6)	0.0092 (6)	0.0062 (6)
C6	0.0440 (8)	0.0432 (8)	0.0302 (7)	0.0191 (6)	0.0081 (6)	0.0047 (6)
C7	0.0520 (9)	0.0461 (8)	0.0309 (7)	0.0244 (7)	0.0101 (6)	0.0076 (6)
C8	0.0552 (10)	0.0493 (9)	0.0363 (8)	0.0215 (8)	0.0109 (7)	0.0055 (7)
C9	0.0847 (14)	0.0649 (11)	0.0316 (8)	0.0274 (10)	0.0090 (8)	0.0024 (8)
C10	0.1114 (18)	0.0719 (13)	0.0364 (10)	0.0311 (13)	0.0228 (11)	0.0187 (9)
C11	0.1029 (17)	0.0547 (11)	0.0495 (11)	0.0206 (11)	0.0241 (11)	0.0198 (9)
C12	0.0718 (12)	0.0473 (9)	0.0394 (9)	0.0199 (8)	0.0099 (8)	0.0067 (7)
C13	0.0517 (10)	0.0700 (11)	0.0510 (10)	0.0342 (9)	0.0207 (8)	0.0183 (9)
C14	0.0456 (13)	0.225 (4)	0.092 (2)	0.0308 (19)	0.0034 (13)	−0.041 (2)
C15	0.121 (3)	0.123 (3)	0.221 (4)	0.095 (2)	0.105 (3)	0.087 (3)
C16	0.0738 (16)	0.136 (2)	0.113 (2)	0.0448 (17)	0.0477 (16)	0.076 (2)
N1	0.0727 (11)	0.0839 (12)	0.0337 (8)	0.0292 (9)	0.0157 (7)	0.0109 (7)
N2	0.0590 (8)	0.0559 (8)	0.0350 (7)	0.0324 (7)	0.0130 (6)	0.0071 (6)
N3	0.0375 (6)	0.0449 (7)	0.0317 (6)	0.0144 (5)	0.0071 (5)	0.0083 (5)
N4	0.0487 (8)	0.0432 (7)	0.0548 (8)	0.0213 (6)	0.0177 (6)	0.0064 (6)
Cl1	0.0707 (3)	0.0591 (3)	0.0495 (3)	0.0047 (2)	0.0110 (2)	0.0012 (2)
Cl2	0.1200 (5)	0.0537 (3)	0.0557 (3)	−0.0004 (3)	0.0043 (3)	−0.0005 (2)

Geometric parameters (Å, º) top

C1—C2	1.347 (3)	C9—H9	0.9300
C1—N1	1.362 (3)	C10—C11	1.375 (3)
C1—H1	0.9300	C10—H10	0.9300
C2—N3	1.376 (2)	C11—C12	1.383 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—N2	1.327 (2)	C12—Cl2	1.7307 (19)
C3—N3	1.378 (2)	C13—N4	1.487 (2)
C3—C4	1.417 (2)	C13—C14	1.494 (3)
C4—N1	1.304 (3)	C13—C16	1.496 (3)
C4—H4	0.9300	C13—C15	1.506 (3)
C5—C6	1.378 (2)	C14—H14A	0.9600
C5—N3	1.3800 (19)	C14—H14B	0.9600
C5—N4	1.388 (2)	C14—H14C	0.9600
C6—N2	1.3650 (19)	C15—H15A	0.9600
C6—C7	1.479 (2)	C15—H15B	0.9600
C7—C12	1.389 (2)	C15—H15C	0.9600
C7—C8	1.391 (2)	C16—H16A	0.9600
C8—C9	1.379 (2)	C16—H16B	0.9600
C8—Cl1	1.7383 (18)	C16—H16C	0.9600
C9—C10	1.370 (3)	N4—H4A	0.8600

C2—C1—N1	124.75 (17)	C11—C12—Cl2	117.84 (15)
C2—C1—H1	117.6	C7—C12—Cl2	119.48 (13)
N1—C1—H1	117.6	N4—C13—C14	109.91 (16)
C1—C2—N3	117.18 (17)	N4—C13—C16	111.05 (16)
C1—C2—H2	121.4	C14—C13—C16	110.3 (3)
N3—C2—H2	121.4	N4—C13—C15	106.32 (19)
N2—C3—N3	111.51 (13)	C14—C13—C15	110.4 (3)
N2—C3—C4	131.36 (16)	C16—C13—C15	108.7 (2)
N3—C3—C4	117.12 (15)	C13—C14—H14A	109.5
N1—C4—C3	122.75 (18)	C13—C14—H14B	109.5
N1—C4—H4	118.6	H14A—C14—H14B	109.5
C3—C4—H4	118.6	C13—C14—H14C	109.5
C6—C5—N3	104.18 (13)	H14A—C14—H14C	109.5
C6—C5—N4	134.65 (14)	H14B—C14—H14C	109.5
N3—C5—N4	121.10 (13)	C13—C15—H15A	109.5
N2—C6—C5	112.36 (13)	C13—C15—H15B	109.5
N2—C6—C7	122.10 (13)	H15A—C15—H15B	109.5
C5—C6—C7	125.53 (13)	C13—C15—H15C	109.5
C12—C7—C8	115.75 (14)	H15A—C15—H15C	109.5
C12—C7—C6	121.53 (14)	H15B—C15—H15C	109.5
C8—C7—C6	122.64 (14)	C13—C16—H16A	109.5
C9—C8—C7	122.83 (17)	C13—C16—H16B	109.5
C9—C8—Cl1	117.98 (14)	H16A—C16—H16B	109.5
C7—C8—Cl1	119.18 (12)	C13—C16—H16C	109.5
C10—C9—C8	119.10 (18)	H16A—C16—H16C	109.5
C10—C9—H9	120.4	H16B—C16—H16C	109.5
C8—C9—H9	120.4	C4—N1—C1	117.39 (16)
C9—C10—C11	120.58 (18)	C3—N2—C6	104.55 (13)
C9—C10—H10	119.7	C2—N3—C3	120.81 (14)
C11—C10—H10	119.7	C2—N3—C5	131.78 (14)
C10—C11—C12	119.06 (19)	C3—N3—C5	107.39 (12)
C10—C11—H11	120.5	C5—N4—C13	121.18 (14)
C12—C11—H11	120.5	C5—N4—H4A	119.4
C11—C12—C7	122.66 (17)	C13—N4—H4A	119.4

N1—C1—C2—N3	−0.2 (3)	C8—C7—C12—Cl2	179.44 (13)
N2—C3—C4—N1	−178.52 (19)	C6—C7—C12—Cl2	2.7 (2)
N3—C3—C4—N1	0.4 (3)	C3—C4—N1—C1	0.2 (3)
N3—C5—C6—N2	0.31 (18)	C2—C1—N1—C4	−0.3 (3)
N4—C5—C6—N2	−176.49 (17)	N3—C3—N2—C6	0.44 (19)
N3—C5—C6—C7	−178.54 (14)	C4—C3—N2—C6	179.42 (19)
N4—C5—C6—C7	4.7 (3)	C5—C6—N2—C3	−0.46 (19)
N2—C6—C7—C12	−71.1 (2)	C7—C6—N2—C3	178.43 (15)
C5—C6—C7—C12	107.6 (2)	C1—C2—N3—C3	0.8 (2)
N2—C6—C7—C8	112.39 (19)	C1—C2—N3—C5	178.89 (16)
C5—C6—C7—C8	−68.9 (2)	N2—C3—N3—C2	178.22 (14)
C12—C7—C8—C9	−1.6 (3)	C4—C3—N3—C2	−0.9 (2)
C6—C7—C8—C9	175.10 (17)	N2—C3—N3—C5	−0.26 (18)
C12—C7—C8—Cl1	177.99 (13)	C4—C3—N3—C5	−179.40 (15)
C6—C7—C8—Cl1	−5.3 (2)	C6—C5—N3—C2	−178.28 (16)
C7—C8—C9—C10	0.9 (3)	N4—C5—N3—C2	−0.9 (3)
Cl1—C8—C9—C10	−178.66 (18)	C6—C5—N3—C3	−0.03 (16)
C8—C9—C10—C11	0.2 (4)	N4—C5—N3—C3	177.31 (14)
C9—C10—C11—C12	−0.5 (4)	C6—C5—N4—C13	−87.5 (2)
C10—C11—C12—C7	−0.3 (4)	N3—C5—N4—C13	96.14 (18)
C10—C11—C12—Cl2	−178.48 (19)	C14—C13—N4—C5	−40.2 (3)
C8—C7—C12—C11	1.3 (3)	C16—C13—N4—C5	82.2 (2)
C6—C7—C12—C11	−175.48 (19)	C15—C13—N4—C5	−159.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.93	2.62	3.500 (3)	158

Symmetry code: (i) −x+2, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆Cl₂N₄
M_r	335.23
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.1482 (4), 9.8553 (5), 11.5265 (6)
α, β, γ (°)	93.218 (2), 99.320 (3), 113.026 (2)
V (Å³)	833.31 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.892, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	12583, 3438, 2941
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.05
No. of reflections	3438
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.40

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N2ⁱ	0.93	2.62	3.500 (3)	158

Symmetry code: (i) −x+2, −y, −z.

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. ZF also thanks the UGC for a meritorious fellowship.

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