2-Amino-4-methyl­pyrimidinium dihydrogen phosphate

Thomas, S.P.; Sunkari, J.

doi:10.1107/S160053681300648X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o529

doi:10.1107/S160053681300648X

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2-Amino-4-methylpyrimidinium dihydrogen phosphate

Sajesh P. Thomas ^a ^* and Jyothi Sunkari ^b

^aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^bDepartment of Chemistry, Kakatiya University, Warangal 506 009, India
^*Correspondence e-mail: jyothisri97@yahoo.co.in

(Received 8 February 2013; accepted 6 March 2013; online 13 March 2013)

A charge-assisted hydrogen-bonding network involving N—H⋯O and O—H⋯O hydrogen bonds stabilizes the crystal of the title salt, C₅H₈N₃⁺·H₂PO₄⁻. The dihydrogen phosphate anions form one-dimensional chains along [100], via O—H⋯O hydrogen bonds. The 2-amino-4-methylpyrimidinium cations are linked to these chains by means of two different kinds of N—H⋯O hydrogen bonds. Neighbouring chains are linked via C—H⋯N and C—H⋯O hydrogen bonds forming two-dimensional slab-like networks lying parallel to (01-1).

Related literature

Intriguing anion clusters formed by the supramolecular assembly of dihydrogen phosphates have been investigated recently (see: Hossain et al., 2012 ). Methylpyrimidine derivatives are known to be synthetic precursors to many bioactive pyrimidine derivatives (see: Xue et al., 1993 ). Metal complexes of pyrimidines (see: Zhu et al., 2008 ) and their proton transfer complexes with mineral acids are reported (see: Aakeroy et al., 2003 ). The infinite O—H⋯O hydrogen-bond chain present in this material is a structural feature suggestive of possible proton conducting behaviour (see: Haile et al., 2001 ).

Experimental

Crystal data

C₅H₈N₃⁺·H₂PO₄⁻
M_r = 207.13
Triclinic, $[P \overline 1]$
a = 6.1720 (2) Å
b = 7.5616 (3) Å
c = 9.9216 (4) Å
α = 100.562 (3)°
β = 99.821 (3)°
γ = 102.279 (4)°
V = 434.07 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.18 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.928, T_max = 0.947
9718 measured reflections
1717 independent reflections
1546 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.088
S = 1.08
1717 reflections
125 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	1.80	2.6100 (18)	168
N1—H1N⋯O2ⁱⁱ	0.86	2.14	3.000 (2)	177
O2—H2⋯O4ⁱⁱⁱ	0.82	1.80	2.5843 (17)	161
N1—H2N⋯O3^iv	0.86	2.01	2.845 (2)	163
N3—H3N⋯O3ⁱⁱ	0.90 (2)	1.73 (2)	2.6276 (19)	173 (2)
C4—H4⋯N2^v	0.93	2.55	3.463 (2)	166
C5—H5B⋯O1^vi	0.96	2.58	3.531 (3)	171
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1; (iv) -x, -y+1, -z+2; (v) x+1, y, z; (vi) -x, -y, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681300648X/ds2227sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300648X/ds2227Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681300648X/ds2227Isup3.cml

checkCIF report

Comment top

The title compound, a multicomponent crystal, AMHP, crystallizes in triclinic P-1, with a protonated 2-amino-4-methylpyrimidine molecule and a dihydrogenphosphate moiety in the asymmetric unit (Fig. 1). The dihydrogenphosphate residue forms a chain via O—H···O hydrogen bonds. 2-Amino-4-methylpyrimidinium cations are linked to these chains by means of two different kinds of N—H···O hydrogen bonds. The crystal packing is stabilized by N—H···O and O—H···O hydrogen bonds and the resulting supramolecular assembly is shown in Figure 2. The infinite hydrogen bond chains present in this structure are of special interest due to the anticipated proton conductivity of the material (see: Haile et al.2001).

Related literature top

Intriguing anion clusters formed by the supramolecular assembly of dihydrogen phosphates have been investigated recently (see: Hossain et al., 2012). Methylpyrimidine derivatives are known to be synthetic precursors to many bioactive pyrimidine derivatives (see: Xue et al., 1993). Metal complexes of pyrimidines (see: Zhu et al., 2008) and their proton transfer complexes with mineral acids are reported (see: Aakeroy et al., 2003). The infinite O—H···O hydrogen-bond chain present in this material is a structural feature suggestive of possible proton conducting behaviour (see: Haile et al., 2001).

Experimental top

The title compound was prepared by treating 2-amino 4-methyl pyramidine with phosphoric acid (H3PO4) in aqueous solution (Scheme 1) in 1:1 molar ratio. The crystals were harvested from the solution after 10 days and suitable crystal for single-crystal X-ray diffraction study were chosen using a polarizing microscope.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. ORTEP view of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. A view of supramolecular chain showing the hydrogen bonding between dihydrogen phosphate residues and the interlinked 2-amino-4-methylpyrimidine molecules.

2-Amino-4-methylpyrimidinium dihydrogen phosphate top

Crystal data top

C₅H₈N₃⁺·H₂PO₄⁻	Z = 2
M_r = 207.13	F(000) = 216
Triclinic, P1	Least Squares Treatment of 25 SET4 setting angles.
Hall symbol: -P 1	D_x = 1.585 Mg m⁻³
a = 6.1720 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5616 (3) Å	Cell parameters from 326 reflections
c = 9.9216 (4) Å	θ = 2.8–26.0°
α = 100.562 (3)°	µ = 0.31 mm⁻¹
β = 99.821 (3)°	T = 295 K
γ = 102.279 (4)°	Block, colourless
V = 434.07 (3) Å³	0.25 × 0.20 × 0.18 mm

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	1717 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1546 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 26.0°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	h = −7→7
T_min = 0.928, T_max = 0.947	k = −9→9
9718 measured reflections	l = −12→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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0449P)² + 0.1805P] where P = (F_o² + 2F_c²)/3
1717 reflections	(Δ/σ)_max < 0.001
125 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₅H₈N₃⁺·H₂PO₄⁻	γ = 102.279 (4)°
M_r = 207.13	V = 434.07 (3) Å³
Triclinic, P1	Z = 2
a = 6.1720 (2) Å	Mo Kα radiation
b = 7.5616 (3) Å	µ = 0.31 mm⁻¹
c = 9.9216 (4) Å	T = 295 K
α = 100.562 (3)°	0.25 × 0.20 × 0.18 mm
β = 99.821 (3)°

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	1717 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	1546 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.947	R_int = 0.027
9718 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.21 e Å⁻³
1717 reflections	Δρ_min = −0.34 e Å⁻³
125 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 e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
N1	0.1136 (3)	0.3869 (2)	1.11795 (16)	0.0405 (5)
N2	−0.0464 (2)	0.1740 (2)	0.90738 (15)	0.0332 (4)
N3	0.3480 (2)	0.2530 (2)	0.99937 (15)	0.0326 (4)
C1	0.1379 (3)	0.2712 (2)	1.00803 (17)	0.0293 (5)
C2	−0.0146 (3)	0.0613 (2)	0.79698 (18)	0.0341 (5)
C3	0.2007 (3)	0.0371 (3)	0.7852 (2)	0.0407 (6)
C4	0.3796 (3)	0.1362 (3)	0.88869 (19)	0.0386 (6)
C5	−0.2202 (4)	−0.0381 (3)	0.6843 (2)	0.0507 (7)
P1	0.28422 (7)	0.48498 (6)	0.64883 (4)	0.0283 (1)
O1	0.0685 (2)	0.31898 (17)	0.59152 (14)	0.0418 (4)
O2	0.4901 (2)	0.39299 (18)	0.64980 (12)	0.0365 (4)
O3	0.2949 (2)	0.5709 (2)	0.79898 (13)	0.0439 (4)
O4	0.29115 (19)	0.61556 (16)	0.55043 (13)	0.0336 (4)
H1N	0.23060	0.44920	1.18240	0.0490*
H2N	−0.01930	0.40020	1.12510	0.0490*
H3	0.21960	−0.04470	0.70830	0.0490*
H3N	0.464 (4)	0.319 (3)	1.071 (2)	0.048 (6)*
H4	0.52500	0.12390	0.88380	0.0460*
H5A	−0.31890	−0.12620	0.71950	0.0760*
H5B	−0.17500	−0.10210	0.60520	0.0760*
H5C	−0.29890	0.05020	0.65580	0.0760*
H1	−0.03370	0.35420	0.54850	0.0630*
H2	0.53240	0.39280	0.57580	0.0550*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0258 (7)	0.0530 (9)	0.0348 (8)	0.0121 (7)	0.0011 (6)	−0.0069 (7)
N2	0.0252 (7)	0.0384 (8)	0.0319 (7)	0.0049 (6)	0.0049 (6)	0.0030 (6)
N3	0.0238 (7)	0.0423 (8)	0.0309 (7)	0.0087 (6)	0.0047 (6)	0.0069 (6)
C1	0.0241 (8)	0.0338 (8)	0.0303 (8)	0.0081 (6)	0.0052 (6)	0.0081 (7)
C2	0.0327 (9)	0.0334 (8)	0.0331 (9)	0.0033 (7)	0.0079 (7)	0.0048 (7)
C3	0.0410 (10)	0.0435 (10)	0.0373 (10)	0.0132 (8)	0.0140 (8)	0.0003 (8)
C4	0.0315 (9)	0.0494 (10)	0.0403 (10)	0.0173 (8)	0.0134 (8)	0.0103 (8)
C5	0.0393 (11)	0.0546 (12)	0.0424 (11)	−0.0023 (9)	0.0047 (8)	−0.0077 (9)
P1	0.0201 (2)	0.0388 (3)	0.0242 (2)	0.0076 (2)	0.0030 (2)	0.0046 (2)
O1	0.0294 (7)	0.0421 (7)	0.0492 (8)	0.0029 (5)	−0.0041 (6)	0.0177 (6)
O2	0.0300 (6)	0.0563 (8)	0.0293 (6)	0.0201 (6)	0.0081 (5)	0.0126 (6)
O3	0.0298 (7)	0.0705 (9)	0.0280 (7)	0.0165 (6)	0.0057 (5)	−0.0015 (6)
O4	0.0238 (6)	0.0396 (6)	0.0379 (7)	0.0078 (5)	0.0066 (5)	0.0106 (5)

Geometric parameters (Å, º) top

P1—O3	1.4964 (13)	N1—H2N	0.8600
P1—O1	1.5623 (14)	N1—H1N	0.8600
P1—O2	1.5725 (14)	N3—H3N	0.90 (2)
P1—O4	1.5098 (13)	C2—C5	1.492 (3)
O1—H1	0.8200	C2—C3	1.401 (3)
O2—H2	0.8200	C3—C4	1.347 (3)
N1—C1	1.319 (2)	C3—H3	0.9300
N2—C2	1.329 (2)	C4—H4	0.9300
N2—C1	1.349 (2)	C5—H5C	0.9600
N3—C1	1.348 (2)	C5—H5A	0.9600
N3—C4	1.347 (2)	C5—H5B	0.9600

P1···H3Nⁱ	2.89 (2)	C2···C1^ix	3.481 (2)
P1···H2Nⁱⁱ	3.1000	C2···O1	3.099 (2)
P1···H1ⁱⁱⁱ	2.8900	C3···O1	3.257 (2)
P1···H1Nⁱ	3.0600	C4···O2	3.395 (2)
P1···H2^iv	2.8800	C5···O1	3.277 (3)
O1···C3	3.257 (2)	C5···H4^viii	2.9800
O1···C5	3.277 (3)	H1···P1ⁱⁱⁱ	2.8900
O1···O4ⁱⁱⁱ	2.6100 (18)	H1···O4ⁱⁱⁱ	1.8000
O1···C2	3.099 (2)	H1···H1ⁱⁱⁱ	2.5500
O2···N1ⁱ	3.000 (2)	H1N···H2ⁱ	2.5200
O2···C4	3.395 (2)	H1N···H3N	2.2400
O2···O4^iv	2.5843 (17)	H1N···P1ⁱ	3.0600
O3···N1ⁱⁱ	2.845 (2)	H1N···O2ⁱ	2.1400
O3···N3ⁱ	2.6276 (19)	H2···O4^iv	1.8000
O4···O1ⁱⁱⁱ	2.6100 (18)	H2···H1Nⁱ	2.5200
O4···O2^iv	2.5843 (17)	H2···H2^iv	2.4500
O1···H5B^v	2.5800	H2···P1^iv	2.8800
O2···H1Nⁱ	2.1400	H2N···P1ⁱⁱ	3.1000
O3···H3Nⁱ	1.73 (2)	H2N···O3ⁱⁱ	2.0100
O3···H2Nⁱⁱ	2.0100	H3···O4^x	2.9100
O4···H2^iv	1.8000	H3···H5B	2.3900
O4···H1ⁱⁱⁱ	1.8000	H3N···H1N	2.2400
O4···H3^vi	2.9100	H3N···P1ⁱ	2.89 (2)
O4···H5A^vii	2.8000	H3N···O3ⁱ	1.73 (2)
N1···O2ⁱ	3.000 (2)	H4···N2^xi	2.5500
N1···O3ⁱⁱ	2.845 (2)	H4···C5^xi	2.9800
N3···O3ⁱ	2.6276 (19)	H5A···O4^xii	2.8000
N2···H4^viii	2.5500	H5B···H3	2.3900
C1···C2^ix	3.481 (2)	H5B···O1^v	2.5800

O3—P1—O4	115.79 (8)	N2—C1—N3	121.54 (15)
O1—P1—O3	109.84 (8)	N2—C2—C3	122.14 (16)
O1—P1—O4	109.55 (7)	N2—C2—C5	116.73 (17)
O1—P1—O2	104.78 (7)	C3—C2—C5	121.13 (17)
O2—P1—O4	110.13 (7)	C2—C3—C4	117.84 (18)
O2—P1—O3	106.13 (7)	N3—C4—C3	120.03 (18)
P1—O1—H1	109.00	C2—C3—H3	121.00
P1—O2—H2	109.00	C4—C3—H3	121.00
C1—N2—C2	117.90 (15)	C3—C4—H4	120.00
C1—N3—C4	120.52 (15)	N3—C4—H4	120.00
H1N—N1—H2N	120.00	C2—C5—H5B	109.00
C1—N1—H1N	120.00	C2—C5—H5C	109.00
C1—N1—H2N	120.00	C2—C5—H5A	109.00
C1—N3—H3N	117.5 (15)	H5A—C5—H5C	109.00
C4—N3—H3N	121.9 (15)	H5B—C5—H5C	109.00
N1—C1—N3	118.80 (16)	H5A—C5—H5B	110.00
N1—C1—N2	119.66 (17)

C2—N2—C1—N1	178.81 (15)	C4—N3—C1—N2	0.1 (2)
C2—N2—C1—N3	−1.3 (2)	C1—N3—C4—C3	0.3 (3)
C1—N2—C2—C3	2.1 (2)	N2—C2—C3—C4	−1.7 (3)
C1—N2—C2—C5	−177.38 (16)	C5—C2—C3—C4	177.75 (19)
C4—N3—C1—N1	−179.98 (18)	C2—C3—C4—N3	0.4 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱⁱⁱ	0.82	1.80	2.6100 (18)	168
N1—H1N···O2ⁱ	0.86	2.14	3.000 (2)	177
O2—H2···O4^iv	0.82	1.80	2.5843 (17)	161
N1—H2N···O3ⁱⁱ	0.86	2.01	2.845 (2)	163
N3—H3N···O3ⁱ	0.90 (2)	1.73 (2)	2.6276 (19)	173 (2)
C4—H4···N2^xi	0.93	2.55	3.463 (2)	166
C5—H5B···O1^v	0.96	2.58	3.531 (3)	171

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

Experimental details

Crystal data
Chemical formula	C₅H₈N₃⁺·H₂PO₄⁻
M_r	207.13
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.1720 (2), 7.5616 (3), 9.9216 (4)
α, β, γ (°)	100.562 (3), 99.821 (3), 102.279 (4)
V (Å³)	434.07 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.928, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	9718, 1717, 1546
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.088, 1.08
No. of reflections	1717
No. of parameters	125
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis PRO (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 2012), Mercury (Macrae et al., 2008), PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

P1—O3	1.4964 (13)	N2—C2	1.329 (2)
P1—O1	1.5623 (14)	N2—C1	1.349 (2)
P1—O2	1.5725 (14)	N3—C1	1.348 (2)
P1—O4	1.5098 (13)	N3—C4	1.347 (2)
N1—C1	1.319 (2)

O3—P1—O4	115.79 (8)	C1—N3—C4	120.52 (15)
O1—P1—O3	109.84 (8)	N1—C1—N3	118.80 (16)
O1—P1—O4	109.55 (7)	N1—C1—N2	119.66 (17)
O1—P1—O2	104.78 (7)	N2—C1—N3	121.54 (15)
O2—P1—O4	110.13 (7)	N2—C2—C3	122.14 (16)
O2—P1—O3	106.13 (7)	N2—C2—C5	116.73 (17)
C1—N2—C2	117.90 (15)	N3—C4—C3	120.03 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.8200	1.8000	2.6100 (18)	168.00
N1—H1N···O2ⁱⁱ	0.8600	2.1400	3.000 (2)	177.00
O2—H2···O4ⁱⁱⁱ	0.8200	1.8000	2.5843 (17)	161.00
N1—H2N···O3^iv	0.8600	2.0100	2.845 (2)	163.00
N3—H3N···O3ⁱⁱ	0.90 (2)	1.73 (2)	2.6276 (19)	173 (2)
C4—H4···N2^v	0.9300	2.5500	3.463 (2)	166.00
C5—H5B···O1^vi	0.9600	2.5800	3.531 (3)	171.00

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

Acknowledgements

SPT thanks UGC for an SRF, JS thanks UGC for research funding. SPT and SJ acknowledge Professor T. N. Guru Row for his support and XRD facility at IISc.

References

Aakeroy, C. B., Beffert, K., Desper, J. & Elisabeth, E. (2003). Cryst. Growth Des. 3, 837–846. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Haile, S. M., Boysen, D. A., Chisholm, C. R. I. & Merle, R. B. (2001). Nature, 410, 910–913. Web of Science CrossRef PubMed CAS Google Scholar
Hossain, M. A., Muhammet, I. K., Avijit, P., Musabbir, A. S. & Frank, R. F. (2012). Cryst. Growth Des. 12, 567–571. Web of Science CSD CrossRef CAS PubMed Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2006). CrysAlis CCD, CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xue, S. J., Zhang, A. D. & Wang, H. T. (1993). Chem. Reagents, 15, 181–182. CAS Google Scholar
Zhu, W., Liu, X. & Wang, H. (2008). Acta Opt. Sin. 28, 1155–1160. CAS Google Scholar