N,N-Diethyl­anilinium 5-(5-chloro-2,4-dinitro­phen­yl)-2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidin-4-olate

Babykala, R.; Kalaivani, D.

doi:10.1107/S1600536813004352

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o398-o399

doi:10.1107/S1600536813004352

Open

access

N,N-Diethylanilinium 5-(5-chloro-2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate

R. Babykala ^a and D. Kalaivani ^a ^*

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

(Received 31 January 2013; accepted 13 February 2013; online 20 February 2013)

In the anion of the title salt, C₁₀H₁₆N⁺·C₁₀H₄ClN₄O₇⁻ [trivial name = N,N-diethylanilinium 5-(3-chloro-4,6,-dinitrophenyl)barbiturate], the dihedral angle between the benzene and pyrimidine rings is 45.49 (6)°. The mean plane of the nitro group, which is ortho-substituted with respect to the pyrimidine ring, is twisted by 41.57 (13)° from the benzene ring, while the mean plane of the nitro group, which is para-substituted, is twisted by 14.41 (12)° from this ring. In the crystal, N—H⋯O hydrogen bonds link cations and anions into chains along [1-10]. Within the chains, inversion-related anionic barbiturate anions form R₂²(8) ring motifs.

Related literature

For different types of interactions between electron-deficient nitro aromatics and bases, see: Jackson & Gazzolo (1900 ); Mulliken (1952 ); Russell & Janzen (1962 ); Blake et al. (1966 ). For donor–acceptor interactions see: Mulliken (1952); Radha et al. (1987 ). For π–π stacking interactions, see: Vembu & Fronczek (2009 ). For the biological activity of pyrimidine and barbiturate derivatives, see: Jain et al. (2006 ); Tripathi (2009 ) and of related barbiturates, see: Kalaivani & Buvaneswari (2010 ). For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009 ); Buvaneswari & Kalaivani (2011 ); Kalaivani & Mangaiyarkarasi (2013 ). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₀H₁₆N⁺·C₁₀H₄ClN₄O₇⁻
M_r = 477.86
Triclinic, $[P \overline 1]$
a = 9.8040 (2) Å
b = 10.2870 (2) Å
c = 11.8260 (2) Å
α = 74.727 (1)°
β = 82.761 (1)°
γ = 71.817 (1)°
V = 1091.87 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.913, T_max = 0.985
18678 measured reflections
3836 independent reflections
3123 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.04
3836 reflections
312 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O5ⁱ	0.83 (2)	2.06 (2)	2.892 (2)	175 (2)
N3—H3A⋯O7ⁱⁱ	0.83 (2)	1.96 (2)	2.794 (2)	180 (3)
N5—H5A⋯O6ⁱⁱⁱ	0.87 (3)	1.82 (3)	2.677 (2)	168 (3)
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y+1, -z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004352/lh5583sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004352/lh5583Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004352/lh5583Isup3.cml

checkCIF report

Comment top

Several types of interactions have been observed between electron deficient nitro aromatic compounds and electron rich species (Jackson et al., 1900; Mulliken, 1952; Russell et al., 1962; Blake et al., 1966). Partial transfer of electrons results in the formation of charge-transfer complexes (Mulliken, 1952; Russell et al., 1962). N,N-diethylaniline usually forms charge transfer complexes with electron deficient nitroaromatics which is revealed through the existence of π···π stacking in single crystal X-ray diffraction studies (Vembu et al.,2009). The title molecular salt is formed upon mixing 1,3-dichloro-4,6-dinitrobenzene (DCDNB), N,N-diethylaniline and barbituric acid in which no significant π···π stacking is observed between nitro aromatic ring and N,N-diethylaniline ring. Barbituric acid (pyrimidine-2,4,6(1H,3H,5H)-trione) and many other pyrimidine derivatives occupy a distinct and unique place in everyday life (Jain et al., 2006). Barbiturates are mainly used to stop convulsion and they also have hypnotic property which is applied for the treatment of psychotic patients, induction of state of sleep and prolonged sleep (Tripathi et al., 2009). The related barbiturates synthesised in our laboratory also possess such properties (Kalaivani & Malarvizhi 2009; Kalaivani & Buvaneswari 2010). Single crystal X-ray analysis of the molecular salts derived from (1-chloro-2,4-dinitrobenzene/2,4,6-trinitrobenzene), N,N-diethylaniline and barbituric acid have already been reported by our group (Buvaneswari & Kalaivani 2011; Kalaivani & Mangaiyarkarasi, 2013).

The molecular structure of the title compound is shown in Fig 1. In the crystal, N—H···O hyrogen bonds link cations and anions into chains (Fig 2) along [110] which incorporate R²₂(8) rings (Bernstein et al., 1995).

Related literature top

For different types of interactions between electron-deficient nitro aromatics and bases, see: Jackson & Gazzolo (1900); Mulliken (1952); Russell & Janzen (1962); Blake et al. (1966). For donor–acceptor interactions see: Mulliken (1952); Radha et al. (1987). For π–π stacking interactions, see: Vembu & Fronczek (2009). For the biological activity of pyrimidine and barbiturate derivatives, see: Jain et al. (2006); Tripathi (2009) and of related barbiturates, see: Kalaivani & Buvaneswari (2010). For the crystal structures of related barbiturates, see: Kalaivani & Malarvizhi (2009); Buvaneswari & Kalaivani (2011); Kalaivani & Mangaiyarkarasi (2013). For hydrogen-bond graph-set motifs, see: Bernstein et al. (1995).

Experimental top

Analytical grade 1,3-dichloro-4,6-dinitrobenzene (DCDNB) and Barbituric acid (BBA) were used as supplied by Aldrich company. N,N-Diethylaniline was distilled under reduced pressure and the fraction boiling over at its boiling point was used. DCDNB (2.37g, 0.01mol) in 15ml of absolute ethanol was mixed with barbituric acid (1.28g, 0.01mol)in 30ml of absolute ethanol. N,N-diethylaniline (3g, 0.01mol) was added to the above mixture, heated to 313K, and shaken well for 5-6 hrs. The solution was kept at room temperature. After a period of two weeks dark reddish orange block-shaped crystals formed in the solution. The crystals were powdered well and washed with 2 to 5ml of ethanol and 50ml of dry ether and recrystallized from absolute alcohol (m.pt :494K ; yield :80 %). Good quality crystals (dark reddish-orange blocks) for single crystal X-ray studies were obtained by slow evaporation of ethanol solution of the title compound at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (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 the title compound showing 30% probability displacement ellipsoids.
	Fig. 2. Part of the crystal structure showing the N—H···O hydrogen bonds as dotted lines.

N,N-Diethylanilinium 5-(5-chloro-2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate top

Crystal data top

C₁₀H₁₆N⁺·C₁₀H₄ClN₄O₇⁻	Z = 2
M_r = 477.86	F(000) = 496
Triclinic, P1	D_x = 1.453 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8040 (2) Å	Cell parameters from 7243 reflections
b = 10.2870 (2) Å	θ = 2.2–27.2°
c = 11.8260 (2) Å	µ = 0.23 mm⁻¹
α = 74.727 (1)°	T = 293 K
β = 82.761 (1)°	Block, red
γ = 71.817 (1)°	0.30 × 0.30 × 0.20 mm
V = 1091.87 (4) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	3836 independent reflections
Radiation source: fine-focus sealed tube	3123 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
T_min = 0.913, T_max = 0.985	k = −12→12
18678 measured reflections	l = −14→14

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0503P)² + 0.5116P] where P = (F_o² + 2F_c²)/3
3836 reflections	(Δ/σ)_max < 0.001
312 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₀H₁₆N⁺·C₁₀H₄ClN₄O₇⁻	γ = 71.817 (1)°
M_r = 477.86	V = 1091.87 (4) Å³
Triclinic, P1	Z = 2
a = 9.8040 (2) Å	Mo Kα radiation
b = 10.2870 (2) Å	µ = 0.23 mm⁻¹
c = 11.8260 (2) Å	T = 293 K
α = 74.727 (1)°	0.30 × 0.30 × 0.20 mm
β = 82.761 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3836 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3123 reflections with I > 2σ(I)
T_min = 0.913, T_max = 0.985	R_int = 0.027
18678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.40 e Å⁻³
3836 reflections	Δρ_min = −0.25 e Å⁻³
312 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > 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
C1	0.0071 (2)	0.0230 (2)	−0.27529 (19)	0.0475 (5)
C2	−0.0626 (2)	0.1317 (2)	−0.36552 (17)	0.0474 (5)
C3	−0.0487 (2)	0.2634 (2)	−0.38156 (17)	0.0477 (5)
H3	−0.0941	0.3359	−0.4425	0.057*
C4	0.0321 (2)	0.2889 (2)	−0.30787 (17)	0.0415 (4)
C5	0.10006 (18)	0.18534 (19)	−0.21224 (16)	0.0374 (4)
C6	0.0869 (2)	0.0517 (2)	−0.20168 (18)	0.0436 (5)
H6	0.1341	−0.0218	−0.1421	0.052*
C7	0.16905 (19)	0.21325 (18)	−0.12259 (16)	0.0377 (4)
C8	0.09802 (19)	0.33217 (19)	−0.07694 (17)	0.0402 (4)
C9	0.2870 (2)	0.2669 (2)	0.05867 (18)	0.0449 (5)
N4	0.35173 (17)	0.15462 (17)	0.01261 (15)	0.0415 (4)
C11	0.3494 (3)	0.6406 (4)	−0.1188 (2)	0.0874 (9)
H11A	0.3532	0.5436	−0.1072	0.131*
H11B	0.2542	0.6937	−0.0985	0.131*
H11C	0.4167	0.6476	−0.0699	0.131*
C12	0.3870 (3)	0.6980 (3)	−0.2442 (2)	0.0762 (8)
H12A	0.3780	0.7973	−0.2564	0.091*
H12B	0.3196	0.6896	−0.2933	0.091*
C13	0.5808 (3)	0.6803 (3)	−0.4067 (2)	0.0747 (7)
H13A	0.6680	0.6141	−0.4293	0.090*
H13B	0.5059	0.6876	−0.4564	0.090*
C14	0.6049 (6)	0.8165 (4)	−0.4284 (4)	0.1406 (17)
H14A	0.5165	0.8850	−0.4140	0.211*
H14B	0.6384	0.8432	−0.5085	0.211*
H14C	0.6756	0.8117	−0.3770	0.211*
C15	0.5662 (2)	0.4699 (3)	−0.25663 (18)	0.0520 (5)
C16	0.6740 (2)	0.3853 (3)	−0.1841 (2)	0.0589 (6)
H16	0.7297	0.4241	−0.1523	0.071*
C17	0.6985 (3)	0.2419 (3)	−0.1592 (2)	0.0736 (7)
H17	0.7704	0.1825	−0.1093	0.088*
C18	0.6163 (4)	0.1865 (3)	−0.2085 (3)	0.0808 (8)
H18	0.6332	0.0894	−0.1922	0.097*
C19	0.5097 (4)	0.2736 (4)	−0.2812 (3)	0.0837 (9)
H19	0.4546	0.2352	−0.3138	0.100*
C20	0.4836 (3)	0.4154 (3)	−0.3062 (2)	0.0694 (7)
H20	0.4113	0.4745	−0.3559	0.083*
N1	0.0461 (2)	0.43164 (19)	−0.33939 (16)	0.0544 (5)
N2	−0.1569 (2)	0.1174 (3)	−0.44496 (18)	0.0654 (6)
N3	0.16215 (17)	0.35220 (18)	0.01183 (15)	0.0448 (4)
C10	0.29895 (19)	0.11832 (18)	−0.07495 (16)	0.0371 (4)
N5	0.5380 (2)	0.6221 (2)	−0.28078 (16)	0.0585 (5)
O1	0.16331 (19)	0.44533 (19)	−0.33559 (18)	0.0795 (6)
O2	−0.05941 (19)	0.52979 (17)	−0.37394 (16)	0.0724 (5)
O3	−0.2340 (2)	0.2254 (3)	−0.50262 (19)	0.1009 (7)
O4	−0.1558 (3)	0.0024 (3)	−0.4513 (2)	0.1051 (8)
O5	0.37052 (14)	0.00914 (13)	−0.10491 (13)	0.0484 (4)
O6	0.33802 (18)	0.28916 (18)	0.13834 (16)	0.0726 (5)
O7	−0.01956 (14)	0.41850 (15)	−0.10903 (13)	0.0552 (4)
Cl1	−0.00919 (8)	−0.14432 (7)	−0.24327 (7)	0.0795 (2)
H4A	0.429 (3)	0.103 (2)	0.0413 (19)	0.050 (6)*
H3A	0.120 (2)	0.420 (2)	0.0409 (19)	0.047 (6)*
H5A	0.590 (3)	0.644 (3)	−0.238 (2)	0.072 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0400 (10)	0.0530 (12)	0.0561 (12)	−0.0093 (9)	−0.0074 (9)	−0.0267 (10)
C2	0.0352 (10)	0.0704 (14)	0.0425 (11)	−0.0100 (9)	−0.0085 (8)	−0.0266 (10)
C3	0.0382 (10)	0.0651 (13)	0.0339 (10)	−0.0044 (9)	−0.0105 (8)	−0.0107 (9)
C4	0.0354 (9)	0.0466 (11)	0.0399 (10)	−0.0052 (8)	−0.0075 (8)	−0.0114 (8)
C5	0.0287 (9)	0.0419 (10)	0.0396 (10)	0.0003 (7)	−0.0082 (7)	−0.0157 (8)
C6	0.0381 (10)	0.0426 (11)	0.0487 (11)	−0.0008 (8)	−0.0153 (8)	−0.0153 (9)
C7	0.0334 (9)	0.0368 (9)	0.0419 (10)	−0.0009 (7)	−0.0133 (8)	−0.0138 (8)
C8	0.0341 (9)	0.0396 (10)	0.0461 (11)	−0.0008 (8)	−0.0134 (8)	−0.0150 (8)
C9	0.0386 (10)	0.0433 (11)	0.0538 (12)	0.0008 (8)	−0.0175 (9)	−0.0212 (9)
N4	0.0323 (8)	0.0398 (9)	0.0508 (10)	0.0047 (7)	−0.0198 (7)	−0.0178 (7)
C11	0.0686 (17)	0.111 (2)	0.0614 (17)	0.0041 (16)	−0.0067 (13)	−0.0204 (16)
C12	0.0681 (16)	0.0864 (19)	0.0613 (16)	0.0003 (14)	−0.0242 (13)	−0.0135 (14)
C13	0.0782 (18)	0.098 (2)	0.0536 (14)	−0.0369 (16)	−0.0194 (13)	−0.0061 (13)
C14	0.221 (5)	0.109 (3)	0.104 (3)	−0.084 (3)	−0.027 (3)	0.008 (2)
C15	0.0459 (11)	0.0741 (15)	0.0426 (11)	−0.0209 (11)	−0.0023 (9)	−0.0205 (10)
C16	0.0425 (11)	0.0852 (17)	0.0492 (13)	−0.0135 (11)	−0.0030 (10)	−0.0218 (12)
C17	0.0590 (15)	0.0819 (19)	0.0656 (16)	−0.0052 (14)	0.0084 (12)	−0.0170 (14)
C18	0.090 (2)	0.0781 (19)	0.0766 (19)	−0.0345 (17)	0.0293 (17)	−0.0260 (16)
C19	0.096 (2)	0.104 (2)	0.0735 (19)	−0.059 (2)	0.0094 (17)	−0.0305 (17)
C20	0.0633 (15)	0.101 (2)	0.0587 (15)	−0.0389 (14)	−0.0094 (12)	−0.0222 (14)
N1	0.0529 (11)	0.0553 (11)	0.0509 (11)	−0.0123 (9)	−0.0147 (9)	−0.0040 (8)
N2	0.0491 (11)	0.1064 (18)	0.0543 (12)	−0.0243 (12)	−0.0102 (9)	−0.0363 (12)
N3	0.0387 (9)	0.0413 (9)	0.0558 (10)	0.0053 (7)	−0.0188 (8)	−0.0267 (8)
C10	0.0336 (9)	0.0348 (9)	0.0431 (10)	−0.0032 (8)	−0.0125 (8)	−0.0127 (8)
N5	0.0554 (11)	0.0807 (14)	0.0446 (10)	−0.0206 (10)	−0.0213 (9)	−0.0142 (10)
O1	0.0631 (11)	0.0739 (12)	0.1013 (14)	−0.0317 (9)	−0.0211 (10)	0.0015 (10)
O2	0.0740 (11)	0.0520 (9)	0.0756 (12)	−0.0005 (8)	−0.0290 (9)	0.0018 (8)
O3	0.0875 (14)	0.1337 (19)	0.0848 (14)	−0.0213 (13)	−0.0548 (12)	−0.0209 (13)
O4	0.1107 (17)	0.1282 (19)	0.1117 (18)	−0.0526 (15)	−0.0386 (14)	−0.0513 (15)
O5	0.0393 (7)	0.0416 (7)	0.0634 (9)	0.0081 (6)	−0.0221 (6)	−0.0258 (7)
O6	0.0622 (10)	0.0751 (11)	0.0873 (12)	0.0129 (8)	−0.0443 (9)	−0.0515 (10)
O7	0.0417 (8)	0.0527 (8)	0.0684 (10)	0.0147 (6)	−0.0284 (7)	−0.0320 (7)
Cl1	0.0822 (5)	0.0605 (4)	0.1107 (6)	−0.0254 (3)	−0.0314 (4)	−0.0274 (4)

Geometric parameters (Å, º) top

C1—C6	1.381 (3)	C12—H12B	0.9700
C1—C2	1.391 (3)	C13—C14	1.444 (4)
C1—Cl1	1.716 (2)	C13—N5	1.511 (3)
C2—C3	1.365 (3)	C13—H13A	0.9700
C2—N2	1.462 (3)	C13—H13B	0.9700
C3—C4	1.371 (3)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.404 (3)	C14—H14C	0.9600
C4—N1	1.463 (3)	C15—C16	1.368 (3)
C5—C6	1.392 (3)	C15—C20	1.376 (3)
C5—C7	1.458 (2)	C15—N5	1.457 (3)
C6—H6	0.9300	C16—C17	1.375 (4)
C7—C8	1.412 (2)	C16—H16	0.9300
C7—C10	1.417 (2)	C17—C18	1.376 (4)
C8—O7	1.247 (2)	C17—H17	0.9300
C8—N3	1.379 (2)	C18—C19	1.367 (4)
C9—O6	1.222 (2)	C18—H18	0.9300
C9—N3	1.348 (2)	C19—C20	1.356 (4)
C9—N4	1.350 (2)	C19—H19	0.9300
N4—C10	1.392 (2)	C20—H20	0.9300
N4—H4A	0.83 (2)	N1—O1	1.208 (2)
C11—C12	1.490 (4)	N1—O2	1.222 (2)
C11—H11A	0.9600	N2—O4	1.201 (3)
C11—H11B	0.9600	N2—O3	1.215 (3)
C11—H11C	0.9600	N3—H3A	0.83 (2)
C12—N5	1.511 (3)	C10—O5	1.239 (2)
C12—H12A	0.9700	N5—H5A	0.87 (3)

C6—C1—C2	118.98 (19)	C14—C13—H13B	108.7
C6—C1—Cl1	117.21 (16)	N5—C13—H13B	108.7
C2—C1—Cl1	123.67 (16)	H13A—C13—H13B	107.6
C3—C2—C1	119.82 (17)	C13—C14—H14A	109.5
C3—C2—N2	115.7 (2)	C13—C14—H14B	109.5
C1—C2—N2	124.4 (2)	H14A—C14—H14B	109.5
C2—C3—C4	120.06 (18)	C13—C14—H14C	109.5
C2—C3—H3	120.0	H14A—C14—H14C	109.5
C4—C3—H3	120.0	H14B—C14—H14C	109.5
C3—C4—C5	122.90 (19)	C16—C15—C20	121.9 (2)
C3—C4—N1	114.53 (17)	C16—C15—N5	118.7 (2)
C5—C4—N1	122.53 (17)	C20—C15—N5	119.4 (2)
C6—C5—C4	114.94 (17)	C15—C16—C17	118.7 (2)
C6—C5—C7	120.57 (16)	C15—C16—H16	120.7
C4—C5—C7	124.27 (17)	C17—C16—H16	120.7
C1—C6—C5	123.20 (18)	C16—C17—C18	119.8 (3)
C1—C6—H6	118.4	C16—C17—H17	120.1
C5—C6—H6	118.4	C18—C17—H17	120.1
C8—C7—C10	119.95 (16)	C19—C18—C17	120.2 (3)
C8—C7—C5	118.54 (15)	C19—C18—H18	119.9
C10—C7—C5	121.33 (15)	C17—C18—H18	119.9
O7—C8—N3	117.64 (16)	C20—C19—C18	120.8 (3)
O7—C8—C7	125.00 (16)	C20—C19—H19	119.6
N3—C8—C7	117.34 (15)	C18—C19—H19	119.6
O6—C9—N3	122.27 (17)	C19—C20—C15	118.6 (3)
O6—C9—N4	121.96 (17)	C19—C20—H20	120.7
N3—C9—N4	115.77 (17)	C15—C20—H20	120.7
C9—N4—C10	125.86 (15)	O1—N1—O2	123.6 (2)
C9—N4—H4A	115.2 (15)	O1—N1—C4	118.06 (18)
C10—N4—H4A	118.9 (15)	O2—N1—C4	118.25 (18)
C12—C11—H11A	109.5	O4—N2—O3	122.8 (2)
C12—C11—H11B	109.5	O4—N2—C2	120.0 (2)
H11A—C11—H11B	109.5	O3—N2—C2	117.2 (2)
C12—C11—H11C	109.5	C9—N3—C8	125.13 (16)
H11A—C11—H11C	109.5	C9—N3—H3A	116.8 (15)
H11B—C11—H11C	109.5	C8—N3—H3A	118.1 (15)
C11—C12—N5	112.2 (2)	O5—C10—N4	117.47 (15)
C11—C12—H12A	109.2	O5—C10—C7	126.66 (16)
N5—C12—H12A	109.2	N4—C10—C7	115.85 (15)
C11—C12—H12B	109.2	C15—N5—C13	110.66 (19)
N5—C12—H12B	109.2	C15—N5—C12	113.4 (2)
H12A—C12—H12B	107.9	C13—N5—C12	113.49 (19)
C14—C13—N5	114.3 (3)	C15—N5—H5A	110.8 (17)
C14—C13—H13A	108.7	C13—N5—H5A	105.5 (17)
N5—C13—H13A	108.7	C12—N5—H5A	102.4 (17)

C6—C1—C2—C3	1.4 (3)	C17—C18—C19—C20	0.2 (4)
Cl1—C1—C2—C3	177.04 (16)	C18—C19—C20—C15	−0.2 (4)
C6—C1—C2—N2	−176.22 (18)	C16—C15—C20—C19	0.6 (4)
Cl1—C1—C2—N2	−0.6 (3)	N5—C15—C20—C19	−178.9 (2)
C1—C2—C3—C4	−0.9 (3)	C3—C4—N1—O1	−136.1 (2)
N2—C2—C3—C4	176.96 (17)	C5—C4—N1—O1	41.9 (3)
C2—C3—C4—C5	−1.9 (3)	C3—C4—N1—O2	40.2 (3)
C2—C3—C4—N1	176.06 (18)	C5—C4—N1—O2	−141.9 (2)
C3—C4—C5—C6	3.8 (3)	C3—C2—N2—O4	166.9 (2)
N1—C4—C5—C6	−173.95 (17)	C1—C2—N2—O4	−15.4 (3)
C3—C4—C5—C7	−170.75 (18)	C3—C2—N2—O3	−13.0 (3)
N1—C4—C5—C7	11.5 (3)	C1—C2—N2—O3	164.7 (2)
C2—C1—C6—C5	0.8 (3)	O6—C9—N3—C8	−179.2 (2)
Cl1—C1—C6—C5	−175.12 (16)	N4—C9—N3—C8	0.4 (3)
C4—C5—C6—C1	−3.2 (3)	O7—C8—N3—C9	178.2 (2)
C7—C5—C6—C1	171.53 (18)	C7—C8—N3—C9	−0.2 (3)
C6—C5—C7—C8	−130.8 (2)	C9—N4—C10—O5	−178.0 (2)
C4—C5—C7—C8	43.4 (3)	C9—N4—C10—C7	3.3 (3)
C6—C5—C7—C10	44.3 (3)	C8—C7—C10—O5	178.5 (2)
C4—C5—C7—C10	−141.4 (2)	C5—C7—C10—O5	3.4 (3)
C10—C7—C8—O7	−176.7 (2)	C8—C7—C10—N4	−3.0 (3)
C5—C7—C8—O7	−1.5 (3)	C5—C7—C10—N4	−178.07 (17)
C10—C7—C8—N3	1.6 (3)	C16—C15—N5—C13	110.6 (2)
C5—C7—C8—N3	176.84 (18)	C20—C15—N5—C13	−69.9 (3)
O6—C9—N4—C10	177.5 (2)	C16—C15—N5—C12	−120.5 (2)
N3—C9—N4—C10	−2.0 (3)	C20—C15—N5—C12	59.0 (3)
C20—C15—C16—C17	−0.9 (3)	C14—C13—N5—C15	−159.4 (3)
N5—C15—C16—C17	178.5 (2)	C14—C13—N5—C12	71.8 (4)
C15—C16—C17—C18	0.9 (4)	C11—C12—N5—C15	54.0 (3)
C16—C17—C18—C19	−0.5 (4)	C11—C12—N5—C13	−178.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O5ⁱ	0.83 (2)	2.06 (2)	2.892 (2)	175 (2)
N3—H3A···O7ⁱⁱ	0.83 (2)	1.96 (2)	2.794 (2)	180 (3)
N5—H5A···O6ⁱⁱⁱ	0.87 (3)	1.82 (3)	2.677 (2)	168 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₆N⁺·C₁₀H₄ClN₄O₇⁻
M_r	477.86
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.8040 (2), 10.2870 (2), 11.8260 (2)
α, β, γ (°)	74.727 (1), 82.761 (1), 71.817 (1)
V (Å³)	1091.87 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.913, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	18678, 3836, 3123
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.04
No. of reflections	3836
No. of parameters	312
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.25

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O5ⁱ	0.83 (2)	2.06 (2)	2.892 (2)	175 (2)
N3—H3A···O7ⁱⁱ	0.83 (2)	1.96 (2)	2.794 (2)	180 (3)
N5—H5A···O6ⁱⁱⁱ	0.87 (3)	1.82 (3)	2.677 (2)	168 (3)

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

Acknowledgements

The authors are thankful to the SAIF, IIT Madras, for the data collection.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Blake, J. A., Evans, M. J. B. & Russell, K. E. (1966). Can. J. Chem. 44, 119–124. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Buvaneswari, M. & Kalaivani, D. (2011). Acta Cryst. E67, o3452. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jackson, C. J. & Gazzolo, F. H. (1900). Am. Chem. J. 23, 376–396. CAS Google Scholar
Jain, S., Chitre, T. S., Miniyar, P. B., Kathiravan, M. K., Bendre, V. S., Veer, S., Shahane, S. R. & Shishoo, C. J. (2006). Curr. Sci. 90, 793–803. CAS Google Scholar
Kalaivani, D. & Buvaneswari, M. (2010). Recent Advances in Clinical Medicine, pp. 255–260. UK: WSEAS Publications. Google Scholar
Kalaivani, D. & Malarvizhi, R. (2009). Acta Cryst. E65, o2548. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kalaivani, D. & Mangaiyarkarasi, G. (2013). Acta Cryst. E69, o3–o4. CSD CrossRef IUCr Journals 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
Mulliken, R. S. (1952). J. Am. Chem. Soc. 74, 811–824. CrossRef CAS Web of Science Google Scholar
Radha, N., Dhoulethbegum, S. & Sahayamary, J. (1987). Indian J. Chem. Sect. A, 26, 1006–1008. Google Scholar
Russell, G. A. & Janzen, E. G. (1962). J. Am. Chem. Soc. 4, 4153–4154. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tripathi, K. D. (2009). In Essentials of Medical Pharmacology, 6th ed. Chennai: Jaypee Brothers. Google Scholar
Vembu, N. & Fronczek, F. R. (2009). Acta Cryst. E65, o111–o112. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o398-o399

doi:10.1107/S1600536813004352

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

N,N-Di­ethyl­anilinium 5-(5-chloro-2,4-di­nitro­phen­yl)-2,6-dioxo-1,2,3,6-tetra­hydro­pyrimidin-4-olate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N,N-Diethylanilinium 5-(5-chloro-2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate