Crystal structure of tri­methyl­ammonium 5-(2,4-di­nitro­phen­yl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidin-4-olate

Gunaseelan, S.; Doraisamyraja, K.

doi:10.1107/S1600536814019977

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 10| October 2014| Pages o1102-o1103

doi:10.1107/S1600536814019977

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Crystal structure of trimethylammonium 5-(2,4-dinitrophenyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate

Sridevi Gunaseelan ^a and Kalaivani Doraisamyraja ^a ^*

^aPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
^*Correspondence e-mail: kalaivbalaj@yahoo.co.in

Edited by A. J. Lough, University of Toronto, Canada (Received 24 July 2014; accepted 4 September 2014; online 13 September 2014)

The asymmetric unit of the title molecular salt, C₃H₁₀N⁺·C₁₂H₉N₄O₇⁻ [alternative name: trimethylammonium 5-(2,4-dinitrophenyl)-1,3-dimethyl barbiturate], contains one anion and two half-occupancy cations. The cations are disordered about inversion centres. The tetrahydropyrimidine ring is essentially planar [maximum deviation = 0.007 (2) Å] and forms a dihedral angle of 41.12 (6)° with the plane of the benzene ring. In the crystal, N—H⋯O hydrogen bonds link the cations to the anions.

Keywords: crystal structure; barbiturates; biological activity; trimethylammonium salt; tetrahydropyrimidin-4-olate salt; anionic σ-complexes.

CCDC reference: 1022943

1. Related literature

For the biological activity of barbiturates, see: Hueso et al. (2003 ); Kalaivani et al. (2008 ); Tripathi (2009 ); Kalaivani & Buvaneswari (2010 ). For various types of anionic σ-complexes, see: Terrier (1982 ); Gnanadoss & Kalaivani (1985 ); Al-Kaysi et al. (2005 ); For barbiturates as carbon-bonded σ-complexes, see: Kalaivani & Malarvizhi (2009 ); Buvaneswari & Kalaivani (2011 ); Kalaivani et al. (2012 ); Babykala & Kalaivani (2012 , 2013 ); Sridevi & Kalaivani (2012 ); Rajamani & Kalaivani (2012 ). For the crystal structure of a related barbiturate, see: Mangaiyarkarasi & Kalaivani (2013 )

2. Experimental

2.1. Crystal data

C₃H₁₀N⁺·C₁₂H₉N₄O₇⁻
M_r = 381.35
Triclinic, $[P \overline 1]$
a = 9.8417 (5) Å
b = 9.9474 (6) Å
c = 10.4241 (5) Å
α = 103.454 (2)°
β = 106.479 (2)°
γ = 100.856 (2)°
V = 915.66 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.35 × 0.35 × 0.30 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 9536, T_max = 9865
16319 measured reflections
4271 independent reflections
2922 reflections with I > 2σ(I)
R_int = 0.026

2.3. Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.164
S = 0.99
4271 reflections
341 parameters
76 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5A⋯O7	0.91 (2)	1.80 (2)	2.666 (3)	156 (2)
N6—H6A⋯O5	0.92 (2)	1.83 (2)	2.737 (3)	171 (2)

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1022943

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814019977/lh5722sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814019977/lh5722Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814019977/lh5722Isup3.cml

checkCIF report

Comment top

Barbiturates are pyrimidine derivatives and most of them have anticonvulsant activity (Hueso et al., 2003; Kalaivani et al., 2008; Tripathi, 2009; Kalaivani & Buvaneswari, 2010). Various different types of anionic sigma complexes such as carbon-bonded, nitrogen-bonded, oxygen-bonded and Spiro-Meisenheimer complexes have been reported by different groups of scientists (Terrier, 1982; Gnanadoss & Kalaivani, 1985; Al-Kaysi et al., 2005). A number of crystalline barbiturates in the form of carbon-bonded sigma complexes have been prepared and reported by our group (Kalaivani & Malarvizhi, 2009; Buvaneswari & Kalaivani, 2011; Kalaivani et al., 2012; Babykala & Kalaivani, 2012; Sridevi & Kalaivani, 2012; Rajamani & Kalaivani, 2012; Babykala & Kalaivani, 2013). The asymmetric unit of a related barbiturate prepared from 1-chloro-2,4-dinitrobenzene (DNCB) and barbituric acid in the presence of trimethylamine (Mangaiyarkarasi & Kalaivani, 2013) comprises of two cations and two anions. However, in the present investigation, the asymmetric unit of the molecular salt is comprised of one 5-(2,4-dinitrophenyl)-1,3-dimethylbarbiturate anion and two half occupancy trimethylammonium cations. The molecular structure of the title compound is shown in Fig. 1. The cations lie on inversion centres and hence are disordered. In the crystal, N—H···O hydrogen bonds exist between the protonated nitrogen atoms of the cations and oxygen atoms of the carbonyl groups of anions. The tetrahydropyrimidine ring is essentially planar (maximum deviation = 0.007 (2) Å for N3) and forms a dihedral angle of 41.12 (6)Å with the benzene ring. The nitro group which para with respect to the junction of two rings forms a dihedral of -5.7 (2)° with the benzene ring and may be involved to a greater extent in electron delocalization with the benzene than the nitro group ortho to the junction of the two rings which forms a dihedral angle of 38.8 (2)° with the benzene ring.

Related literature top

For the biological activity of barbiturates, see: Hueso et al. (2003); Kalaivani et al. (2008); Tripathi (2009); Kalaivani & Buvaneswari (2010). For various types of anionic σ-complexes, see: Terrier (1982); Gnanadoss & Kalaivani (1985); Al-Kaysi et al. (2005); For barbiturates as carbon-bonded σ-complexes, see: Kalaivani & Malarvizhi (2009); Buvaneswari & Kalaivani (2011); Kalaivani et al. (2012); Babykala & Kalaivani (2012, 2013); Sridevi & Kalaivani (2012); Rajamani & Kalaivani (2012). For the crystal structure of a related barbiturate, see: Mangaiyarkarasi & Kalaivani (2013)

Experimental top

Analytical grade 1-chloro-2,4-dinitrobenzene (2.02 g,0.01 mol) was dissolved in 20 ml of absolute alcohol. 1,3-Dimethylbarbituric acid (1.56 g,0.01 mol) was also dissolved in 30 ml of absolute alcohol separately. These two solutions were then mixed. To this mixture, 4 ml of trimethylamine (0.03 mol) was added and shaken well for 5–6 hrs. The slightly turbid solution obtained was filtered and kept as such at 298K. After a period of three weeks, dark shiny maroon red coloured crystals of the title salt crystallized out from the solution. The crystals were filtered, powdered well using agate mortar and washed with 30 ml of dry ether. The dry solid of the title compound obtained was quickly washed with 1 ml of absolute alcohol to remove unreacted reactants and finally with 25 ml of dry ether. The pure powder was recrystllized from hot etanol (Yield: 80%; m.pt; 513 K). Good quality single crystals, suitable for X-ray diffraction studies, were obtained by slow evaporation of a solution of the title compound in ethanol at room temperature. The crystals obtained were non-hygroscopic and extraordinarily stable at room temperature. Solubility at 298 K: 2.78 g/100 mL(water); 4.58 g/100 mL(Ethanol); 17.78 g/100 mL(DMSO).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of title compound showing 30% probability displacement ellipsoids. The cations are half occupancy.

Trimethylammonium 5-(2,4-dinitrophenyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate top

Crystal data top

C₃H₁₀N⁺·C₁₂H₉N₄O₇⁻	Z = 2
M_r = 381.35	F(000) = 400
Triclinic, P1	D_x = 1.383 Mg m⁻³
a = 9.8417 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9474 (6) Å	Cell parameters from 5386 reflections
c = 10.4241 (5) Å	θ = 2.1–27.5°
α = 103.454 (2)°	µ = 0.11 mm⁻¹
β = 106.479 (2)°	T = 293 K
γ = 100.856 (2)°	Block, red
V = 915.66 (9) Å³	0.35 × 0.35 × 0.30 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2922 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
ω and ϕ scan	θ_max = 27.7°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
T_min = 9536, T_max = 9865	k = −12→12
16319 measured reflections	l = −13→13
4271 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0891P)² + 0.1912P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.164	(Δ/σ)_max < 0.001
S = 0.99	Δρ_max = 0.23 e Å⁻³
4271 reflections	Δρ_min = −0.20 e Å⁻³
341 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
76 restraints	Extinction coefficient: 0.020 (4)

Crystal data top

C₃H₁₀N⁺·C₁₂H₉N₄O₇⁻	γ = 100.856 (2)°
M_r = 381.35	V = 915.66 (9) Å³
Triclinic, P1	Z = 2
a = 9.8417 (5) Å	Mo Kα radiation
b = 9.9474 (6) Å	µ = 0.11 mm⁻¹
c = 10.4241 (5) Å	T = 293 K
α = 103.454 (2)°	0.35 × 0.35 × 0.30 mm
β = 106.479 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4271 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2922 reflections with I > 2σ(I)
T_min = 9536, T_max = 9865	R_int = 0.026
16319 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	76 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.23 e Å⁻³
4271 reflections	Δρ_min = −0.20 e Å⁻³
341 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.3976 (2)	0.7207 (3)	0.07803 (19)	0.0655 (6)
C2	0.2837 (2)	0.6256 (2)	0.08545 (17)	0.0548 (5)
H2	0.2434	0.5342	0.0208	0.066*
C3	0.22965 (18)	0.66915 (18)	0.19261 (16)	0.0440 (4)
C4	0.29063 (16)	0.80221 (18)	0.29787 (16)	0.0424 (4)
C5	0.40705 (19)	0.8947 (2)	0.28249 (19)	0.0584 (5)
H5	0.4508	0.9853	0.3481	0.070*
C6	0.4590 (2)	0.8561 (3)	0.1734 (2)	0.0712 (6)
H6	0.5347	0.9208	0.1644	0.085*
C7	0.24320 (16)	0.84301 (17)	0.41888 (15)	0.0415 (4)
C8	0.21150 (17)	0.74090 (18)	0.48671 (16)	0.0435 (4)
C9	0.1589 (2)	0.9213 (2)	0.65492 (18)	0.0560 (5)
C10	0.23385 (19)	0.98455 (19)	0.46730 (18)	0.0507 (4)
C11	0.1303 (3)	0.6789 (3)	0.6741 (3)	0.0840 (7)
H11A	0.1415	0.5884	0.6277	0.126*
H11B	0.0301	0.6674	0.6704	0.126*
H11C	0.1944	0.7116	0.7704	0.126*
C12	0.1746 (3)	1.1619 (2)	0.6375 (2)	0.0740 (6)
H12A	0.1987	1.2185	0.5799	0.111*
H12B	0.2405	1.2061	0.7326	0.111*
H12C	0.0752	1.1559	0.6342	0.111*
N1	0.4546 (2)	0.6754 (3)	−0.0364 (2)	0.0970 (8)
N2	0.09232 (17)	0.56946 (15)	0.18014 (14)	0.0511 (4)
N3	0.18912 (16)	1.01709 (16)	0.58517 (15)	0.0531 (4)
N4	0.16852 (17)	0.78490 (17)	0.60370 (15)	0.0529 (4)
O1	0.4045 (2)	0.5528 (3)	−0.1143 (2)	0.1098 (7)
O2	0.5474 (3)	0.7651 (4)	−0.0482 (3)	0.1804 (16)
O3	0.0792 (2)	0.44075 (15)	0.13971 (17)	0.0812 (5)
O4	−0.00550 (14)	0.61913 (14)	0.20145 (14)	0.0609 (4)
O5	0.22047 (16)	0.61540 (14)	0.45327 (13)	0.0597 (4)
O6	0.2581 (2)	1.08059 (16)	0.41394 (18)	0.0814 (5)
O7	0.1253 (2)	0.95645 (19)	0.75936 (16)	0.0872 (5)
N5	−0.0051 (4)	0.9761 (3)	0.9524 (3)	0.0548 (8)	0.5
H5A	0.0157 (18)	0.9501 (17)	0.8715 (19)	0.066*	0.5
C13	0.0093 (9)	1.1276 (5)	0.9872 (7)	0.0839 (16)	0.5
H13A	−0.062 (5)	1.134 (8)	0.905 (4)	0.126*	0.5
H13B	0.106 (3)	1.180 (6)	0.993 (6)	0.126*	0.5
H13C	−0.010 (6)	1.166 (6)	1.070 (4)	0.126*	0.5
C14	−0.1578 (5)	0.8892 (6)	0.9182 (5)	0.0772 (12)	0.5
H14A	−0.155 (6)	0.791 (3)	0.896 (5)	0.116*	0.5
H14B	−0.217 (6)	0.909 (5)	0.841 (3)	0.116*	0.5
H14C	−0.188 (6)	0.913 (5)	0.998 (4)	0.116*	0.5
C15	0.0966 (8)	0.9352 (8)	1.0574 (6)	0.0886 (17)	0.5
H15A	0.094 (7)	0.834 (2)	1.037 (7)	0.133*	0.5
H15B	0.087 (7)	0.966 (6)	1.148 (4)	0.133*	0.5
H15C	0.193 (4)	0.987 (5)	1.062 (7)	0.133*	0.5
N6	0.4670 (5)	0.5181 (5)	0.4932 (5)	0.0741 (11)	0.5
H6A	0.381 (2)	0.544 (2)	0.4697 (18)	0.089*	0.5
C16	0.4046 (7)	0.3737 (6)	0.3630 (6)	0.0930 (15)	0.5
H16A	0.426 (6)	0.307 (6)	0.413 (6)	0.140*	0.5
H16B	0.441 (6)	0.364 (7)	0.288 (5)	0.140*	0.5
H16C	0.302 (3)	0.367 (7)	0.334 (6)	0.140*	0.5
C17	0.5736 (8)	0.6071 (8)	0.4681 (12)	0.117 (3)	0.5
H17A	0.623 (8)	0.537 (7)	0.436 (7)	0.176*	0.5
H17B	0.647 (7)	0.679 (6)	0.551 (4)	0.176*	0.5
H17C	0.545 (4)	0.651 (6)	0.396 (5)	0.176*	0.5
C18	0.4811 (9)	0.4741 (12)	0.6114 (7)	0.111 (3)	0.5
H18A	0.393 (3)	0.443 (7)	0.631 (5)	0.166*	0.5
H18B	0.558 (5)	0.536 (7)	0.695 (5)	0.166*	0.5
H18C	0.510 (8)	0.389 (5)	0.574 (8)	0.166*	0.5

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0500 (10)	0.1118 (17)	0.0387 (9)	0.0263 (11)	0.0228 (8)	0.0172 (10)
C2	0.0573 (10)	0.0737 (12)	0.0377 (8)	0.0300 (9)	0.0197 (7)	0.0106 (8)
C3	0.0482 (8)	0.0543 (10)	0.0350 (8)	0.0210 (7)	0.0183 (6)	0.0129 (7)
C4	0.0397 (7)	0.0541 (9)	0.0346 (7)	0.0155 (7)	0.0139 (6)	0.0121 (7)
C5	0.0464 (9)	0.0752 (13)	0.0454 (9)	0.0029 (8)	0.0181 (7)	0.0112 (9)
C6	0.0459 (9)	0.1101 (18)	0.0544 (11)	0.0043 (10)	0.0249 (8)	0.0231 (12)
C7	0.0404 (7)	0.0468 (9)	0.0351 (8)	0.0110 (6)	0.0152 (6)	0.0064 (6)
C8	0.0445 (8)	0.0548 (10)	0.0349 (8)	0.0194 (7)	0.0168 (6)	0.0117 (7)
C9	0.0517 (9)	0.0693 (12)	0.0403 (9)	0.0141 (8)	0.0210 (7)	−0.0002 (8)
C10	0.0517 (9)	0.0468 (10)	0.0464 (9)	0.0059 (7)	0.0196 (7)	0.0038 (7)
C11	0.119 (2)	0.0999 (18)	0.0632 (13)	0.0394 (15)	0.0570 (14)	0.0414 (13)
C12	0.0747 (13)	0.0577 (12)	0.0777 (14)	0.0182 (10)	0.0309 (11)	−0.0072 (10)
N1	0.0689 (12)	0.170 (2)	0.0540 (11)	0.0302 (14)	0.0373 (10)	0.0186 (14)
N2	0.0666 (9)	0.0447 (8)	0.0390 (7)	0.0118 (7)	0.0222 (6)	0.0046 (6)
N3	0.0530 (8)	0.0492 (8)	0.0498 (8)	0.0115 (6)	0.0226 (6)	−0.0024 (7)
N4	0.0604 (9)	0.0676 (10)	0.0393 (7)	0.0214 (7)	0.0264 (6)	0.0172 (7)
O1	0.1167 (15)	0.164 (2)	0.0614 (10)	0.0629 (14)	0.0513 (10)	0.0114 (12)
O2	0.145 (2)	0.251 (3)	0.1205 (19)	−0.023 (2)	0.1083 (19)	−0.003 (2)
O3	0.1220 (13)	0.0443 (8)	0.0793 (10)	0.0157 (8)	0.0525 (10)	0.0058 (7)
O4	0.0511 (7)	0.0642 (8)	0.0588 (8)	0.0074 (6)	0.0239 (6)	0.0030 (6)
O5	0.0829 (9)	0.0629 (8)	0.0538 (7)	0.0374 (7)	0.0356 (7)	0.0264 (6)
O6	0.1232 (13)	0.0492 (8)	0.0846 (11)	0.0192 (8)	0.0583 (10)	0.0191 (7)
O7	0.1065 (12)	0.1035 (12)	0.0624 (9)	0.0314 (10)	0.0580 (9)	0.0071 (8)
N5	0.086 (2)	0.0557 (19)	0.0494 (17)	0.0395 (17)	0.0426 (18)	0.0251 (15)
C13	0.126 (5)	0.060 (3)	0.094 (4)	0.042 (3)	0.063 (4)	0.031 (3)
C14	0.082 (3)	0.080 (3)	0.064 (3)	0.016 (2)	0.030 (2)	0.010 (2)
C15	0.100 (4)	0.117 (5)	0.077 (3)	0.063 (4)	0.032 (3)	0.050 (4)
N6	0.081 (3)	0.082 (3)	0.104 (3)	0.048 (2)	0.059 (3)	0.055 (2)
C16	0.106 (4)	0.081 (4)	0.090 (4)	0.026 (3)	0.039 (3)	0.016 (3)
C17	0.087 (4)	0.076 (4)	0.195 (9)	0.017 (3)	0.042 (5)	0.065 (5)
C18	0.106 (5)	0.192 (9)	0.083 (4)	0.090 (6)	0.054 (4)	0.067 (5)

Geometric parameters (Å, º) top

C1—C2	1.358 (3)	C13—C14ⁱ	1.577 (10)
C1—C6	1.377 (3)	C13—H13A	0.962 (19)
C1—N1	1.471 (2)	C13—H13B	0.971 (19)
C2—C3	1.385 (2)	C13—H13C	0.944 (18)
C2—H2	0.9300	C14—C13ⁱ	1.577 (10)
C3—C4	1.403 (2)	C14—C15ⁱ	1.669 (9)
C3—N2	1.471 (2)	C14—N5ⁱ	1.819 (6)
C4—C5	1.400 (2)	C14—H14A	0.962 (18)
C4—C7	1.463 (2)	C14—H14B	0.938 (18)
C5—C6	1.379 (3)	C14—H14C	0.956 (18)
C5—H5	0.9300	C15—C13ⁱ	1.019 (8)
C6—H6	0.9300	C15—N5ⁱ	1.375 (6)
C7—C8	1.403 (2)	C15—C14ⁱ	1.669 (9)
C7—C10	1.411 (2)	C15—H15A	0.972 (19)
C8—O5	1.243 (2)	C15—H15B	0.960 (19)
C8—N4	1.404 (2)	C15—H15C	0.973 (19)
C9—O7	1.219 (2)	N6—N6ⁱⁱ	0.796 (6)
C9—N3	1.365 (3)	N6—C18ⁱⁱ	1.340 (8)
C9—N4	1.370 (2)	N6—C17	1.367 (8)
C10—O6	1.231 (2)	N6—C18	1.381 (7)
C10—N3	1.408 (2)	N6—C17ⁱⁱ	1.419 (8)
C11—N4	1.470 (3)	N6—C16	1.603 (7)
C11—H11A	0.9600	N6—C16ⁱⁱ	1.632 (8)
C11—H11B	0.9600	N6—H6A	0.92 (2)
C11—H11C	0.9600	C16—C18ⁱⁱ	1.621 (12)
C12—N3	1.466 (2)	C16—N6ⁱⁱ	1.633 (8)
C12—H12A	0.9600	C16—C17ⁱⁱ	1.673 (13)
C12—H12B	0.9600	C16—H16A	0.955 (19)
C12—H12C	0.9600	C16—H16B	0.938 (19)
N1—O2	1.206 (3)	C16—H16C	0.953 (19)
N1—O1	1.215 (3)	C17—C18ⁱⁱ	0.949 (9)
N2—O4	1.2122 (19)	C17—N6ⁱⁱ	1.419 (8)
N2—O3	1.2205 (19)	C17—C16ⁱⁱ	1.673 (13)
N5—N5ⁱ	0.964 (5)	C17—H17A	0.98 (2)
N5—C13ⁱ	1.328 (6)	C17—H17B	0.97 (2)
N5—C15ⁱ	1.375 (6)	C17—H17C	0.955 (18)
N5—C13	1.435 (6)	C18—C17ⁱⁱ	0.949 (9)
N5—C15	1.450 (6)	C18—N6ⁱⁱ	1.340 (8)
N5—C14	1.482 (6)	C18—C16ⁱⁱ	1.621 (12)
N5—C14ⁱ	1.819 (6)	C18—H18A	0.957 (18)
N5—H5A	0.914 (19)	C18—H18B	0.956 (19)
C13—C15ⁱ	1.019 (8)	C18—H18C	0.971 (19)
C13—N5ⁱ	1.328 (6)

C2—C1—C6	121.79 (16)	N5—C14—H14C	110 (4)
C2—C1—N1	117.9 (2)	C13ⁱ—C14—H14C	90 (3)
C6—C1—N1	120.3 (2)	C15ⁱ—C14—H14C	89 (3)
C1—C2—C3	117.72 (17)	N5ⁱ—C14—H14C	78 (3)
C1—C2—H2	121.1	H14A—C14—H14C	109 (3)
C3—C2—H2	121.1	H14B—C14—H14C	113 (3)
C2—C3—C4	123.94 (16)	C13ⁱ—C15—N5ⁱ	72.0 (5)
C2—C3—N2	114.20 (15)	C13ⁱ—C15—N5	62.2 (4)
C4—C3—N2	121.62 (13)	N5ⁱ—C15—N5	39.8 (2)
C5—C4—C3	114.84 (14)	C13ⁱ—C15—C14ⁱ	127.8 (6)
C5—C4—C7	121.04 (15)	N5ⁱ—C15—C14ⁱ	57.3 (3)
C3—C4—C7	124.08 (14)	N5—C15—C14ⁱ	70.9 (4)
C6—C5—C4	122.27 (18)	C13ⁱ—C15—H15A	69 (4)
C6—C5—H5	118.9	N5ⁱ—C15—H15A	141 (4)
C4—C5—H5	118.9	N5—C15—H15A	117 (5)
C5—C6—C1	119.30 (18)	C14ⁱ—C15—H15A	159 (3)
C5—C6—H6	120.3	C13ⁱ—C15—H15B	93 (4)
C1—C6—H6	120.3	N5ⁱ—C15—H15B	73 (4)
C8—C7—C10	121.30 (14)	N5—C15—H15B	112 (4)
C8—C7—C4	119.04 (14)	C14ⁱ—C15—H15B	84 (4)
C10—C7—C4	119.64 (15)	H15A—C15—H15B	108 (3)
O5—C8—N4	117.22 (15)	C13ⁱ—C15—H15C	158 (4)
O5—C8—C7	125.47 (14)	N5ⁱ—C15—H15C	109 (4)
N4—C8—C7	117.30 (15)	N5—C15—H15C	104 (4)
O7—C9—N3	121.10 (19)	C14ⁱ—C15—H15C	53 (4)
O7—C9—N4	121.4 (2)	H15A—C15—H15C	107 (3)
N3—C9—N4	117.52 (14)	H15B—C15—H15C	109 (3)
O6—C10—N3	117.41 (16)	N6ⁱⁱ—N6—C18ⁱⁱ	75.8 (6)
O6—C10—C7	125.85 (16)	N6ⁱⁱ—N6—C17	77.1 (7)
N3—C10—C7	116.72 (16)	C18ⁱⁱ—N6—C17	41.0 (4)
N4—C11—H11A	109.5	N6ⁱⁱ—N6—C18	70.2 (7)
N4—C11—H11B	109.5	C18ⁱⁱ—N6—C18	146.0 (3)
H11A—C11—H11B	109.5	C17—N6—C18	127.1 (6)
N4—C11—H11C	109.5	N6ⁱⁱ—N6—C17ⁱⁱ	69.8 (7)
H11A—C11—H11C	109.5	C18ⁱⁱ—N6—C17ⁱⁱ	126.1 (6)
H11B—C11—H11C	109.5	C17—N6—C17ⁱⁱ	146.9 (3)
N3—C12—H12A	109.5	C18—N6—C17ⁱⁱ	39.6 (4)
N3—C12—H12B	109.5	N6ⁱⁱ—N6—C16	77.8 (7)
H12A—C12—H12B	109.5	C18ⁱⁱ—N6—C16	66.1 (5)
N3—C12—H12C	109.5	C17—N6—C16	106.5 (6)
H12A—C12—H12C	109.5	C18—N6—C16	105.7 (6)
H12B—C12—H12C	109.5	C17ⁱⁱ—N6—C16	66.9 (6)
O2—N1—O1	124.0 (2)	N6ⁱⁱ—N6—C16ⁱⁱ	73.7 (8)
O2—N1—C1	116.9 (3)	C18ⁱⁱ—N6—C16ⁱⁱ	106.1 (5)
O1—N1—C1	119.1 (2)	C17—N6—C16ⁱⁱ	67.1 (6)
O4—N2—O3	123.40 (16)	C18—N6—C16ⁱⁱ	64.5 (5)
O4—N2—C3	118.26 (14)	C17ⁱⁱ—N6—C16ⁱⁱ	102.6 (6)
O3—N2—C3	118.14 (15)	C16—N6—C16ⁱⁱ	151.5 (2)
C9—N3—C10	123.73 (15)	N6ⁱⁱ—N6—H6A	170.3 (15)
C9—N3—C12	117.55 (16)	C18ⁱⁱ—N6—H6A	104.8 (11)
C10—N3—C12	118.73 (17)	C17—N6—H6A	109.9 (11)
C9—N4—C8	123.40 (15)	C18—N6—H6A	108.7 (11)
C9—N4—C11	118.16 (15)	C17ⁱⁱ—N6—H6A	103.0 (11)
C8—N4—C11	118.44 (17)	C16—N6—H6A	93.5 (12)
N5ⁱ—N5—C13ⁱ	75.7 (4)	C16ⁱⁱ—N6—H6A	114.8 (11)
N5ⁱ—N5—C15ⁱ	74.3 (4)	N6—C16—C18ⁱⁱ	49.1 (3)
C13ⁱ—N5—C15ⁱ	127.0 (4)	N6—C16—N6ⁱⁱ	28.5 (2)
N5ⁱ—N5—C13	63.7 (4)	C18ⁱⁱ—C16—N6ⁱⁱ	50.2 (3)
C13ⁱ—N5—C13	139.4 (3)	N6—C16—C17ⁱⁱ	51.3 (3)
C15ⁱ—N5—C13	42.4 (3)	C18ⁱⁱ—C16—C17ⁱⁱ	96.6 (4)
N5ⁱ—N5—C15	65.9 (4)	N6ⁱⁱ—C16—C17ⁱⁱ	48.8 (3)
C13ⁱ—N5—C15	42.7 (4)	N6—C16—H16A	99 (4)
C15ⁱ—N5—C15	140.2 (2)	C18ⁱⁱ—C16—H16A	125 (4)
C13—N5—C15	113.9 (4)	N6ⁱⁱ—C16—H16A	80 (4)
N5ⁱ—N5—C14	93.7 (4)	C17ⁱⁱ—C16—H16A	53 (4)
C13ⁱ—N5—C14	68.1 (4)	N6—C16—H16B	121 (4)
C15ⁱ—N5—C14	71.4 (4)	C18ⁱⁱ—C16—H16B	72 (4)
C13—N5—C14	112.9 (4)	N6ⁱⁱ—C16—H16B	110 (4)
C15—N5—C14	110.2 (4)	C17ⁱⁱ—C16—H16B	152 (4)
N5ⁱ—N5—C14ⁱ	54.4 (4)	H16A—C16—H16B	112 (3)
C13ⁱ—N5—C14ⁱ	100.0 (4)	N6—C16—H16C	101 (4)
C15ⁱ—N5—C14ⁱ	96.7 (4)	C18ⁱⁱ—C16—H16C	119 (4)
C13—N5—C14ⁱ	56.5 (4)	N6ⁱⁱ—C16—H16C	127 (4)
C15—N5—C14ⁱ	60.2 (4)	C17ⁱⁱ—C16—H16C	96 (4)
C14—N5—C14ⁱ	148.1 (2)	H16A—C16—H16C	110 (3)
N5ⁱ—N5—H5A	161.2 (12)	H16B—C16—H16C	113 (3)
C13ⁱ—N5—H5A	111.6 (10)	C18ⁱⁱ—C17—N6	68.0 (6)
C15ⁱ—N5—H5A	110.8 (10)	C18ⁱⁱ—C17—N6ⁱⁱ	68.0 (6)
C13—N5—H5A	107.2 (11)	N6—C17—N6ⁱⁱ	33.1 (3)
C15—N5—H5A	107.0 (11)	C18ⁱⁱ—C17—C16ⁱⁱ	128.5 (9)
C14—N5—H5A	105.1 (11)	N6—C17—C16ⁱⁱ	64.0 (5)
C14ⁱ—N5—H5A	106.8 (11)	N6ⁱⁱ—C17—C16ⁱⁱ	61.8 (5)
C15ⁱ—C13—N5ⁱ	75.1 (5)	C18ⁱⁱ—C17—H17A	61 (5)
C15ⁱ—C13—N5	65.6 (5)	N6—C17—H17A	99 (5)
N5ⁱ—C13—N5	40.6 (3)	N6ⁱⁱ—C17—H17A	70 (5)
C15ⁱ—C13—C14ⁱ	134.6 (6)	C16ⁱⁱ—C17—H17A	109 (4)
N5ⁱ—C13—C14ⁱ	60.6 (4)	C18ⁱⁱ—C17—H17B	167 (4)
N5—C13—C14ⁱ	74.1 (4)	N6—C17—H17B	115 (5)
C15ⁱ—C13—H13A	56 (4)	N6ⁱⁱ—C17—H17B	107 (4)
N5ⁱ—C13—H13A	129 (4)	C16ⁱⁱ—C17—H17B	51 (5)
N5—C13—H13A	102 (5)	H17A—C17—H17B	106 (3)
C14ⁱ—C13—H13A	159 (4)	C18ⁱⁱ—C17—H17C	78 (4)
C15ⁱ—C13—H13B	158 (3)	N6—C17—H17C	119.0 (18)
N5ⁱ—C13—H13B	117 (4)	N6ⁱⁱ—C17—H17C	143 (3)
N5—C13—H13B	111 (4)	C16ⁱⁱ—C17—H17C	142 (4)
C14ⁱ—C13—H13B	57 (4)	H17A—C17—H17C	108 (3)
H13A—C13—H13B	107 (3)	H17B—C17—H17C	109 (3)
C15ⁱ—C13—H13C	89 (3)	C17ⁱⁱ—C18—N6ⁱⁱ	71.0 (7)
N5ⁱ—C13—H13C	76 (4)	C17ⁱⁱ—C18—N6	72.4 (7)
N5—C13—H13C	114 (4)	N6ⁱⁱ—C18—N6	34.0 (3)
C14ⁱ—C13—H13C	89 (4)	C17ⁱⁱ—C18—C16ⁱⁱ	134.5 (9)
H13A—C13—H13C	112 (3)	N6ⁱⁱ—C18—C16ⁱⁱ	64.8 (5)
H13B—C13—H13C	111 (3)	N6—C18—C16ⁱⁱ	65.3 (5)
N5—C14—C13ⁱ	51.3 (3)	C17ⁱⁱ—C18—H18A	78 (4)
N5—C14—C15ⁱ	51.3 (3)	N6ⁱⁱ—C18—H18A	143 (3)
C13ⁱ—C14—C15ⁱ	96.3 (3)	N6—C18—H18A	117.4 (17)
N5—C14—N5ⁱ	31.9 (2)	C16ⁱⁱ—C18—H18A	136 (4)
C13ⁱ—C14—N5ⁱ	49.4 (3)	C17ⁱⁱ—C18—H18B	161 (5)
C15ⁱ—C14—N5ⁱ	48.9 (3)	N6ⁱⁱ—C18—H18B	105 (4)
N5—C14—H14A	106 (4)	N6—C18—H18B	116 (5)
C13ⁱ—C14—H14A	69 (3)	C16ⁱⁱ—C18—H18B	50 (5)
C15ⁱ—C14—H14A	156 (3)	H18A—C18—H18B	110 (3)
N5ⁱ—C14—H14A	118 (3)	C17ⁱⁱ—C18—H18C	51 (5)
N5—C14—H14B	107 (4)	N6ⁱⁱ—C18—H18C	67 (5)
C13ⁱ—C14—H14B	154 (4)	N6—C18—H18C	94 (5)
C15ⁱ—C14—H14B	73 (3)	C16ⁱⁱ—C18—H18C	116 (4)
N5ⁱ—C14—H14B	122 (4)	H18A—C18—H18C	108 (3)
H14A—C14—H14B	112 (3)	H18B—C18—H18C	110 (3)

C6—C1—C2—C3	0.4 (3)	C13ⁱ—N5—C14—C15ⁱ	145.1 (4)
N1—C1—C2—C3	−179.46 (18)	C13—N5—C14—C15ⁱ	9.2 (4)
C1—C2—C3—C4	−3.7 (3)	C15—N5—C14—C15ⁱ	137.8 (3)
C1—C2—C3—N2	170.69 (17)	C14ⁱ—N5—C14—C15ⁱ	72.1 (4)
C2—C3—C4—C5	4.0 (3)	C13ⁱ—N5—C14—N5ⁱ	73.0 (4)
N2—C3—C4—C5	−169.94 (16)	C15ⁱ—N5—C14—N5ⁱ	−72.1 (4)
C2—C3—C4—C7	−173.67 (16)	C13—N5—C14—N5ⁱ	−62.9 (4)
N2—C3—C4—C7	12.4 (2)	C15—N5—C14—N5ⁱ	65.6 (4)
C3—C4—C5—C6	−1.2 (3)	C14ⁱ—N5—C14—N5ⁱ	−0.002 (2)
C7—C4—C5—C6	176.58 (18)	N5ⁱ—N5—C15—C13ⁱ	95.0 (6)
C4—C5—C6—C1	−1.8 (3)	C15ⁱ—N5—C15—C13ⁱ	95.0 (6)
C2—C1—C6—C5	2.3 (3)	C13—N5—C15—C13ⁱ	138.1 (4)
N1—C1—C6—C5	−177.9 (2)	C14—N5—C15—C13ⁱ	10.1 (6)
C5—C4—C7—C8	−136.83 (18)	C14ⁱ—N5—C15—C13ⁱ	156.4 (6)
C3—C4—C7—C8	40.7 (2)	C13ⁱ—N5—C15—N5ⁱ	−95.0 (6)
C5—C4—C7—C10	41.5 (2)	C15ⁱ—N5—C15—N5ⁱ	0.000 (1)
C3—C4—C7—C10	−140.90 (17)	C13—N5—C15—N5ⁱ	43.1 (4)
C10—C7—C8—O5	−178.11 (16)	C14—N5—C15—N5ⁱ	−84.9 (5)
C4—C7—C8—O5	0.2 (2)	C14ⁱ—N5—C15—N5ⁱ	61.4 (4)
C10—C7—C8—N4	0.7 (2)	N5ⁱ—N5—C15—C14ⁱ	−61.4 (4)
C4—C7—C8—N4	179.05 (14)	C13ⁱ—N5—C15—C14ⁱ	−156.4 (6)
C8—C7—C10—O6	−179.24 (18)	C15ⁱ—N5—C15—C14ⁱ	−61.4 (4)
C4—C7—C10—O6	2.4 (3)	C13—N5—C15—C14ⁱ	−18.3 (4)
C8—C7—C10—N3	−0.9 (2)	C14—N5—C15—C14ⁱ	−146.3 (2)
C4—C7—C10—N3	−179.29 (14)	N6ⁱⁱ—N6—C16—C18ⁱⁱ	−79.7 (6)
C2—C1—N1—O2	174.1 (3)	C17—N6—C16—C18ⁱⁱ	−7.4 (6)
C6—C1—N1—O2	−5.7 (4)	C18—N6—C16—C18ⁱⁱ	−144.9 (3)
C2—C1—N1—O1	−4.5 (3)	C17ⁱⁱ—N6—C16—C18ⁱⁱ	−152.8 (6)
C6—C1—N1—O1	175.7 (2)	C16ⁱⁱ—N6—C16—C18ⁱⁱ	−79.7 (6)
C2—C3—N2—O4	−135.67 (17)	C18ⁱⁱ—N6—C16—N6ⁱⁱ	79.7 (6)
C4—C3—N2—O4	38.8 (2)	C17—N6—C16—N6ⁱⁱ	72.4 (7)
C2—C3—N2—O3	39.5 (2)	C18—N6—C16—N6ⁱⁱ	−65.1 (6)
C4—C3—N2—O3	−146.01 (17)	C17ⁱⁱ—N6—C16—N6ⁱⁱ	−73.0 (7)
O7—C9—N3—C10	177.49 (17)	C16ⁱⁱ—N6—C16—N6ⁱⁱ	0.004 (2)
N4—C9—N3—C10	−2.1 (3)	N6ⁱⁱ—N6—C16—C17ⁱⁱ	73.0 (7)
O7—C9—N3—C12	−2.2 (3)	C18ⁱⁱ—N6—C16—C17ⁱⁱ	152.8 (6)
N4—C9—N3—C12	178.26 (16)	C17—N6—C16—C17ⁱⁱ	145.4 (4)
O6—C10—N3—C9	−179.88 (18)	C18—N6—C16—C17ⁱⁱ	7.9 (6)
C7—C10—N3—C9	1.7 (2)	C16ⁱⁱ—N6—C16—C17ⁱⁱ	73.0 (7)
O6—C10—N3—C12	−0.2 (3)	N6ⁱⁱ—N6—C17—C18ⁱⁱ	83.2 (10)
C7—C10—N3—C12	−178.68 (16)	C18—N6—C17—C18ⁱⁱ	135.7 (5)
O7—C9—N4—C8	−177.78 (17)	C17ⁱⁱ—N6—C17—C18ⁱⁱ	83.2 (10)
N3—C9—N4—C8	1.8 (3)	C16—N6—C17—C18ⁱⁱ	10.3 (8)
O7—C9—N4—C11	2.9 (3)	C16ⁱⁱ—N6—C17—C18ⁱⁱ	160.8 (9)
N3—C9—N4—C11	−177.50 (18)	C18ⁱⁱ—N6—C17—N6ⁱⁱ	−83.2 (10)
O5—C8—N4—C9	177.77 (15)	C18—N6—C17—N6ⁱⁱ	52.5 (7)
C7—C8—N4—C9	−1.1 (2)	C17ⁱⁱ—N6—C17—N6ⁱⁱ	−0.001 (2)
O5—C8—N4—C11	−2.9 (2)	C16—N6—C17—N6ⁱⁱ	−72.9 (7)
C7—C8—N4—C11	178.16 (17)	C16ⁱⁱ—N6—C17—N6ⁱⁱ	77.6 (8)
N5ⁱ—N5—C13—C15ⁱ	−95.4 (6)	N6ⁱⁱ—N6—C17—C16ⁱⁱ	−77.6 (8)
C13ⁱ—N5—C13—C15ⁱ	−95.4 (6)	C18ⁱⁱ—N6—C17—C16ⁱⁱ	−160.8 (9)
C15—N5—C13—C15ⁱ	−139.6 (4)	C18—N6—C17—C16ⁱⁱ	−25.1 (7)
C14—N5—C13—C15ⁱ	−13.0 (6)	C17ⁱⁱ—N6—C17—C16ⁱⁱ	−77.6 (8)
C14ⁱ—N5—C13—C15ⁱ	−158.6 (6)	C16—N6—C17—C16ⁱⁱ	−150.5 (3)
C13ⁱ—N5—C13—N5ⁱ	0.000 (1)	N6ⁱⁱ—N6—C18—C17ⁱⁱ	−81.9 (10)
C15ⁱ—N5—C13—N5ⁱ	95.4 (6)	C18ⁱⁱ—N6—C18—C17ⁱⁱ	−81.9 (10)
C15—N5—C13—N5ⁱ	−44.1 (4)	C17—N6—C18—C17ⁱⁱ	−137.2 (5)
C14—N5—C13—N5ⁱ	82.5 (5)	C16—N6—C18—C17ⁱⁱ	−11.5 (8)
C14ⁱ—N5—C13—N5ⁱ	−63.1 (4)	C16ⁱⁱ—N6—C18—C17ⁱⁱ	−162.9 (8)
N5ⁱ—N5—C13—C14ⁱ	63.1 (4)	C18ⁱⁱ—N6—C18—N6ⁱⁱ	−0.002 (2)
C13ⁱ—N5—C13—C14ⁱ	63.1 (4)	C17—N6—C18—N6ⁱⁱ	−55.2 (8)
C15ⁱ—N5—C13—C14ⁱ	158.6 (6)	C17ⁱⁱ—N6—C18—N6ⁱⁱ	81.9 (10)
C15—N5—C13—C14ⁱ	19.0 (4)	C16—N6—C18—N6ⁱⁱ	70.4 (7)
C14—N5—C13—C14ⁱ	145.6 (3)	C16ⁱⁱ—N6—C18—N6ⁱⁱ	−80.9 (7)
N5ⁱ—N5—C14—C13ⁱ	−73.0 (4)	N6ⁱⁱ—N6—C18—C16ⁱⁱ	80.9 (7)
C15ⁱ—N5—C14—C13ⁱ	−145.1 (4)	C18ⁱⁱ—N6—C18—C16ⁱⁱ	80.9 (7)
C13—N5—C14—C13ⁱ	−135.9 (3)	C17—N6—C18—C16ⁱⁱ	25.7 (7)
C15—N5—C14—C13ⁱ	−7.4 (4)	C17ⁱⁱ—N6—C18—C16ⁱⁱ	162.9 (8)
C14ⁱ—N5—C14—C13ⁱ	−73.0 (4)	C16—N6—C18—C16ⁱⁱ	151.4 (3)
N5ⁱ—N5—C14—C15ⁱ	72.1 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O7	0.91 (2)	1.80 (2)	2.666 (3)	156 (2)
N6—H6A···O5	0.92 (2)	1.83 (2)	2.737 (3)	171 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5A···O7	0.91 (2)	1.80 (2)	2.666 (3)	156.0 (15)
N6—H6A···O5	0.92 (2)	1.83 (2)	2.737 (3)	170.5 (17)

Acknowledgements

The authors are grateful to SERB–DST, New Delhi, for the financial support and SAIF, IIT Madras, for the data collection.

References

Al-Kaysi, R. O., Mueller, A. M., Ahn, T. S., Lee, S. & Bardeen, C. J. (2005). Langmuir, 21, 7990–7994. Web of Science PubMed CAS Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Babykala, R. & Kalaivani, D. (2012). Acta Cryst. E68, o541. Web of Science CSD CrossRef IUCr Journals Google Scholar
Babykala, R. & Kalaivani, D. (2013). Acta Cryst. E69, o398–o399. CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o1433–o1434. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gnanadoss, L. M. & Kalaivani, D. (1985). J. Org. Chem. 50, 1174–1178. CrossRef CAS Web of Science Google Scholar
Hueso, F., Moreno, M. N., Martinez, J. M. & Ramirez, M. J. (2003). J. Inorg. Biochem. 94, 326–334. Web of Science PubMed Google Scholar
Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255–260. Cambridge: WSEAS Publications. Google Scholar
Kalaivani, D., Buvaneswari, M. & Rajeswari, S. (2012). Acta Cryst. E68, o29–o30. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kalaivani, D., Malarvizhi, R. & Subbalakshmi, R. (2008). Med. Chem. Res. 17, 369–373. Web of Science CrossRef CAS 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
Mangaiyarkarasi, G. & Kalaivani, D. (2013). Acta Cryst. E69, o592–o593. CSD CrossRef CAS IUCr Journals Google Scholar
Rajamani, K. & Kalaivani, D. (2012). Acta Cryst. E68, o2395. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sridevi, G. & Kalaivani, D. (2012). Acta Cryst. E68, o1044. CSD CrossRef IUCr Journals Google Scholar
Terrier, F. (1982). Chem. Rev. 82, 77–152. CrossRef CAS Web of Science Google Scholar
Tripathi, K. D. (2009). In Essentials of Medical Pharmacology, 6th ed. Chennai: Jaypee Brothers. Google Scholar

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Volume 70| Part 10| October 2014| Pages o1102-o1103

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of tri­methyl­ammonium 5-(2,4-di­nitro­phen­yl)-1,3-di­methyl-2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidin-4-olate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of trimethylammonium 5-(2,4-dinitrophenyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate