Triethyl-ammonium 2,4-dinitro-phenyl-barbiturate.

In the title mol-ecular salt [systematic name: triethylammonium 5-(2,4-dinitrophenyl)-2,6-dioxo-1,2,3,6-tetrahydropyrim-idin-4-olate], C(6)H(16)N(+)·C(10)H(5)N(4)O(7) (-), the cation and anion are linked by an N-H⋯O hydrogen bond. In the crystal, inversion-related barbiturate rings are centrosymmetrically connected through pairs of N-H⋯O hydrogen bonds, forming R(2) (2)(8)R(2) (2)(8) ring motifs.

Related literature

For further information on the anti­convulsant properties of the title compound and general background, see: Kalaivani et al. (2008 ▶). For a related structure, see: Craven (1964 ▶). For data on hydrogen-bond motifs in organic crystals, see: Allen et al. (1998 ▶).

Experimental

Crystal data

C6H16N+·C10H5N4O7 −

M = 395.38

Monoclinic,

a = 29.7900 (8) Å

b = 10.4533 (3) Å

c = 11.9606 (3) Å

β = 97.903 (1)°

V = 3689.20 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.942, T max = 0.971

32882 measured reflections

3217 independent reflections

2493 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.109

S = 1.04

3217 reflections

268 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altornare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036976/hb5061sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036976/hb5061Isup2.hkl

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

C6H16N+·C10H5N4O7−	F(000) = 1664
Mr = 395.38	Dx = 1.424 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8875 reflections
a = 29.7900 (8) Å	θ = 2.5–24.5°
b = 10.4533 (3) Å	µ = 0.11 mm−1
c = 11.9606 (3) Å	T = 293 K
β = 97.903 (1)°	Block, maroon
V = 3689.20 (17) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3217 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω and φ scan	θmax = 24.9°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −35→35
Tmin = 0.942, Tmax = 0.971	k = −12→12
32882 measured reflections	l = −13→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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0467P)2 + 3.5895P] where P = (Fo2 + 2Fc2)/3
3217 reflections	(Δ/σ)max < 0.001
268 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.19 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	0.49607 (6)	0.30537 (17)	0.47768 (17)	0.0402 (5)
C2	0.43235 (6)	0.33505 (16)	0.32947 (15)	0.0336 (4)
C3	0.42904 (6)	0.20117 (16)	0.31524 (15)	0.0339 (4)
C4	0.45876 (6)	0.11860 (16)	0.38266 (15)	0.0348 (4)
C5	0.39223 (6)	0.15178 (15)	0.23248 (14)	0.0321 (4)
C6	0.34717 (6)	0.18925 (16)	0.22995 (14)	0.0317 (4)
C7	0.31314 (6)	0.15443 (17)	0.14568 (15)	0.0372 (4)
H7	0.2835	0.1820	0.1463	0.045*
C8	0.32439 (6)	0.07760 (17)	0.06070 (15)	0.0371 (4)
C9	0.36810 (7)	0.03485 (18)	0.05876 (16)	0.0408 (5)
H9	0.3751	−0.0173	0.0006	0.049*
C10	0.40118 (7)	0.07127 (17)	0.14501 (16)	0.0387 (5)
H10	0.4305	0.0411	0.1449	0.046*
C11	0.39539 (7)	0.7557 (2)	0.27509 (19)	0.0498 (5)
H11A	0.4126	0.7659	0.3495	0.060*
H11B	0.3779	0.8331	0.2577	0.060*
C12	0.42740 (9)	0.7390 (3)	0.1905 (2)	0.0700 (7)
H12A	0.4425	0.6580	0.2022	0.105*
H12B	0.4495	0.8065	0.1991	0.105*
H12C	0.4109	0.7419	0.1158	0.105*
C13	0.33902 (8)	0.6466 (2)	0.37901 (18)	0.0570 (6)
H13A	0.3268	0.7316	0.3877	0.068*
H13B	0.3137	0.5877	0.3659	0.068*
C14	0.36764 (10)	0.6107 (2)	0.48412 (19)	0.0702 (7)
H14A	0.3803	0.5274	0.4757	0.105*
H14B	0.3497	0.6092	0.5448	0.105*
H14C	0.3916	0.6720	0.5006	0.105*
C15	0.33107 (7)	0.6313 (2)	0.17207 (18)	0.0494 (5)
H15A	0.3145	0.5521	0.1768	0.059*
H15B	0.3478	0.6243	0.1083	0.059*
C16	0.29765 (8)	0.7386 (3)	0.1498 (2)	0.0690 (7)
H16A	0.2792	0.7424	0.2096	0.104*
H16B	0.2787	0.7240	0.0793	0.104*
H16C	0.3136	0.8179	0.1464	0.104*
N1	0.46707 (5)	0.37959 (15)	0.40826 (14)	0.0416 (4)
N2	0.49133 (5)	0.17742 (14)	0.46111 (14)	0.0387 (4)
N3	0.33250 (6)	0.26868 (15)	0.31972 (14)	0.0414 (4)
N4	0.28841 (7)	0.04383 (17)	−0.03058 (15)	0.0515 (5)
N5	0.36397 (6)	0.64590 (15)	0.27695 (13)	0.0387 (4)
O1	0.52439 (5)	0.35119 (13)	0.55104 (13)	0.0575 (4)
O2	0.40649 (4)	0.41466 (11)	0.27608 (11)	0.0425 (4)
O3	0.45764 (5)	−0.00016 (12)	0.38115 (12)	0.0496 (4)
O4	0.35005 (6)	0.25162 (15)	0.41664 (12)	0.0582 (4)
O5	0.30234 (5)	0.34649 (15)	0.29215 (14)	0.0582 (4)
O6	0.24947 (6)	0.0672 (2)	−0.01885 (17)	0.0964 (7)
O7	0.29920 (6)	−0.00325 (19)	−0.11540 (15)	0.0808 (6)
H1	0.4688 (7)	0.459 (2)	0.4188 (17)	0.046 (6)*
H2	0.5078 (7)	0.133 (2)	0.5064 (19)	0.050 (6)*
H5	0.3796 (7)	0.577 (2)	0.2791 (17)	0.044 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0371 (10)	0.0255 (9)	0.0527 (12)	−0.0008 (8)	−0.0122 (9)	−0.0017 (8)
C2	0.0337 (10)	0.0252 (9)	0.0386 (10)	0.0012 (7)	−0.0070 (8)	0.0001 (7)
C3	0.0353 (10)	0.0231 (9)	0.0395 (10)	0.0002 (7)	−0.0087 (8)	−0.0012 (7)
C4	0.0373 (10)	0.0231 (9)	0.0408 (10)	0.0002 (7)	−0.0061 (8)	−0.0025 (7)
C5	0.0393 (10)	0.0194 (8)	0.0344 (10)	−0.0015 (7)	−0.0058 (8)	0.0035 (7)
C6	0.0388 (10)	0.0247 (9)	0.0300 (9)	−0.0034 (7)	−0.0005 (8)	0.0003 (7)
C7	0.0349 (10)	0.0353 (10)	0.0394 (11)	−0.0039 (8)	−0.0016 (8)	0.0028 (8)
C8	0.0443 (11)	0.0295 (9)	0.0335 (10)	−0.0057 (8)	−0.0092 (8)	−0.0003 (8)
C9	0.0537 (12)	0.0284 (9)	0.0382 (10)	0.0004 (9)	−0.0019 (9)	−0.0062 (8)
C10	0.0410 (11)	0.0283 (9)	0.0441 (11)	0.0031 (8)	−0.0044 (9)	−0.0032 (8)
C11	0.0497 (13)	0.0374 (11)	0.0579 (13)	−0.0010 (9)	−0.0077 (10)	0.0042 (10)
C12	0.0664 (16)	0.0652 (16)	0.0797 (18)	−0.0033 (13)	0.0145 (14)	0.0200 (14)
C13	0.0710 (15)	0.0484 (13)	0.0549 (14)	0.0046 (11)	0.0203 (12)	−0.0038 (11)
C14	0.107 (2)	0.0575 (15)	0.0484 (14)	0.0062 (14)	0.0207 (14)	0.0066 (11)
C15	0.0528 (13)	0.0432 (12)	0.0495 (12)	−0.0039 (10)	−0.0029 (10)	−0.0025 (10)
C16	0.0522 (14)	0.0725 (17)	0.0766 (17)	0.0098 (12)	−0.0119 (12)	0.0106 (14)
N1	0.0444 (10)	0.0180 (8)	0.0554 (10)	−0.0014 (7)	−0.0185 (8)	−0.0011 (7)
N2	0.0391 (9)	0.0227 (8)	0.0480 (10)	0.0024 (7)	−0.0161 (8)	0.0015 (7)
N3	0.0436 (10)	0.0370 (9)	0.0435 (10)	−0.0082 (8)	0.0053 (8)	−0.0049 (7)
N4	0.0576 (12)	0.0441 (10)	0.0466 (11)	−0.0041 (9)	−0.0151 (9)	−0.0070 (8)
N5	0.0508 (10)	0.0255 (8)	0.0392 (9)	0.0094 (8)	0.0041 (7)	0.0014 (7)
O1	0.0558 (9)	0.0284 (7)	0.0756 (10)	−0.0022 (6)	−0.0366 (8)	−0.0024 (7)
O2	0.0464 (8)	0.0225 (6)	0.0522 (8)	0.0041 (6)	−0.0162 (6)	0.0014 (6)
O3	0.0594 (9)	0.0205 (7)	0.0600 (9)	0.0023 (6)	−0.0234 (7)	−0.0011 (6)
O4	0.0764 (11)	0.0639 (10)	0.0330 (8)	−0.0074 (8)	0.0031 (7)	−0.0084 (7)
O5	0.0499 (9)	0.0512 (9)	0.0730 (11)	0.0085 (8)	0.0067 (8)	−0.0125 (8)
O6	0.0495 (11)	0.150 (2)	0.0822 (14)	−0.0072 (12)	−0.0177 (10)	−0.0414 (13)
O7	0.0883 (13)	0.0883 (14)	0.0564 (11)	0.0148 (11)	−0.0234 (9)	−0.0350 (10)

C1—O1	1.228 (2)	C12—H12A	0.9600
C1—N2	1.357 (2)	C12—H12B	0.9600
C1—N1	1.357 (2)	C12—H12C	0.9600
C2—O2	1.248 (2)	C13—C14	1.467 (3)
C2—N1	1.381 (2)	C13—N5	1.514 (3)
C2—C3	1.412 (2)	C13—H13A	0.9700
C3—C4	1.408 (2)	C13—H13B	0.9700
C3—C5	1.466 (2)	C14—H14A	0.9600
C4—O3	1.242 (2)	C14—H14B	0.9600
C4—N2	1.396 (2)	C14—H14C	0.9600
C5—C6	1.395 (2)	C15—N5	1.490 (2)
C5—C10	1.397 (3)	C15—C16	1.498 (3)
C6—C7	1.377 (2)	C15—H15A	0.9700
C6—N3	1.471 (2)	C15—H15B	0.9700
C7—C8	1.373 (3)	C16—H16A	0.9600
C7—H7	0.9300	C16—H16B	0.9600
C8—C9	1.380 (3)	C16—H16C	0.9600
C8—N4	1.464 (2)	N1—H1	0.84 (2)
C9—C10	1.379 (3)	N2—H2	0.82 (2)
C9—H9	0.9300	N3—O4	1.217 (2)
C10—H10	0.9300	N3—O5	1.223 (2)
C11—N5	1.483 (3)	N4—O7	1.210 (2)
C11—C12	1.492 (3)	N4—O6	1.212 (2)
C11—H11A	0.9700	N5—H5	0.85 (2)
C11—H11B	0.9700
O1—C1—N2	122.44 (17)	C14—C13—N5	113.4 (2)
O1—C1—N1	122.11 (17)	C14—C13—H13A	108.9
N2—C1—N1	115.45 (16)	N5—C13—H13A	108.9
O2—C2—N1	118.42 (15)	C14—C13—H13B	108.9
O2—C2—C3	124.84 (16)	N5—C13—H13B	108.9
N1—C2—C3	116.74 (15)	H13A—C13—H13B	107.7
C4—C3—C2	120.71 (16)	C13—C14—H14A	109.5
C4—C3—C5	121.58 (15)	C13—C14—H14B	109.5
C2—C3—C5	117.63 (15)	H14A—C14—H14B	109.5
O3—C4—N2	117.69 (16)	C13—C14—H14C	109.5
O3—C4—C3	126.22 (16)	H14A—C14—H14C	109.5
N2—C4—C3	116.04 (15)	H14B—C14—H14C	109.5
C6—C5—C10	115.80 (16)	N5—C15—C16	114.65 (18)
C6—C5—C3	122.95 (16)	N5—C15—H15A	108.6
C10—C5—C3	121.05 (17)	C16—C15—H15A	108.6
C7—C6—C5	123.46 (16)	N5—C15—H15B	108.6
C7—C6—N3	114.89 (16)	C16—C15—H15B	108.6
C5—C6—N3	121.64 (15)	H15A—C15—H15B	107.6
C8—C7—C6	117.81 (17)	C15—C16—H16A	109.5
C8—C7—H7	121.1	C15—C16—H16B	109.5
C6—C7—H7	121.1	H16A—C16—H16B	109.5
C7—C8—C9	121.94 (16)	C15—C16—H16C	109.5
C7—C8—N4	117.70 (18)	H16A—C16—H16C	109.5
C9—C8—N4	120.34 (17)	H16B—C16—H16C	109.5
C10—C9—C8	118.50 (17)	C1—N1—C2	125.39 (16)
C10—C9—H9	120.8	C1—N1—H1	116.9 (14)
C8—C9—H9	120.8	C2—N1—H1	117.4 (14)
C9—C10—C5	122.44 (18)	C1—N2—C4	125.53 (16)
C9—C10—H10	118.8	C1—N2—H2	114.8 (16)
C5—C10—H10	118.8	C4—N2—H2	119.4 (16)
N5—C11—C12	112.55 (18)	O4—N3—O5	123.88 (17)
N5—C11—H11A	109.1	O4—N3—C6	118.73 (16)
C12—C11—H11A	109.1	O5—N3—C6	117.36 (16)
N5—C11—H11B	109.1	O7—N4—O6	123.20 (18)
C12—C11—H11B	109.1	O7—N4—C8	118.14 (19)
H11A—C11—H11B	107.8	O6—N4—C8	118.64 (19)
C11—C12—H12A	109.5	C11—N5—C15	114.20 (16)
C11—C12—H12B	109.5	C11—N5—C13	112.90 (17)
H12A—C12—H12B	109.5	C15—N5—C13	109.90 (17)
C11—C12—H12C	109.5	C11—N5—H5	107.9 (14)
H12A—C12—H12C	109.5	C15—N5—H5	103.4 (14)
H12B—C12—H12C	109.5	C13—N5—H5	107.9 (14)
O2—C2—C3—C4	−177.48 (19)	C3—C5—C10—C9	−172.52 (17)
N1—C2—C3—C4	2.8 (3)	O1—C1—N1—C2	−175.1 (2)
O2—C2—C3—C5	−0.7 (3)	N2—C1—N1—C2	4.3 (3)
N1—C2—C3—C5	179.64 (17)	O2—C2—N1—C1	175.63 (19)
C2—C3—C4—O3	176.4 (2)	C3—C2—N1—C1	−4.7 (3)
C5—C3—C4—O3	−0.2 (3)	O1—C1—N2—C4	177.2 (2)
C2—C3—C4—N2	−1.0 (3)	N1—C1—N2—C4	−2.2 (3)
C5—C3—C4—N2	−177.72 (17)	O3—C4—N2—C1	−177.0 (2)
C4—C3—C5—C6	126.7 (2)	C3—C4—N2—C1	0.7 (3)
C2—C3—C5—C6	−50.1 (3)	C7—C6—N3—O4	142.69 (17)
C4—C3—C5—C10	−58.6 (3)	C5—C6—N3—O4	−36.5 (2)
C2—C3—C5—C10	124.63 (19)	C7—C6—N3—O5	−35.6 (2)
C10—C5—C6—C7	−2.2 (3)	C5—C6—N3—O5	145.17 (17)
C3—C5—C6—C7	172.76 (17)	C7—C8—N4—O7	166.62 (19)
C10—C5—C6—N3	176.93 (15)	C9—C8—N4—O7	−12.1 (3)
C3—C5—C6—N3	−8.1 (3)	C7—C8—N4—O6	−11.6 (3)
C5—C6—C7—C8	0.7 (3)	C9—C8—N4—O6	169.7 (2)
N3—C6—C7—C8	−178.44 (16)	C12—C11—N5—C15	−66.8 (2)
C6—C7—C8—C9	0.5 (3)	C12—C11—N5—C13	166.72 (18)
C6—C7—C8—N4	−178.22 (16)	C16—C15—N5—C11	−65.2 (3)
C7—C8—C9—C10	−0.2 (3)	C16—C15—N5—C13	62.8 (2)
N4—C8—C9—C10	178.53 (17)	C14—C13—N5—C11	−73.7 (2)
C8—C9—C10—C5	−1.4 (3)	C14—C13—N5—C15	157.55 (19)
C6—C5—C10—C9	2.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.84 (2)	2.02 (2)	2.861 (2)	177 (2)
N2—H2···O3ii	0.82 (2)	2.10 (2)	2.918 (2)	172 (2)
N5—H5···O2	0.85 (2)	1.88 (2)	2.730 (2)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.84 (2)	2.02 (2)	2.861 (2)	177 (2)
N2—H2⋯O3ii	0.82 (2)	2.10 (2)	2.918 (2)	172 (2)
N5—H5⋯O2	0.85 (2)	1.88 (2)	2.730 (2)	172 (2)

Symmetry codes: (i) ; (ii) .