N,N-Diethyl-anilinium 5-(5-chloro-2,4-dinitro-phen-yl)-2,6-dioxo-1,2,3,6-tetra-hydro-pyrimidin-4-olate.

In the anion of the title salt, C10H16N(+)·C10H4ClN4O7(-) [trivial name = N,N-diethyl-anilinium 5-(3-chloro-4,6,-dinitro-phen-yl)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 R2(2)(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 = 477.86

Triclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.117

S = 1.04

3836 reflections

312 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.25 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004352/lh5583sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004352/lh5583Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H16N+·C10H4ClN4O7−	Z = 2
Mr = 477.86	F(000) = 496
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0503P)2 + 0.5116P] where P = (Fo2 + 2Fc2)/3
3836 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) ; (iii) .