Five pseudopolymorphs and a cocrystal of nitro­furan­toin

The anti­biotic nitro­furan­toin {systematic name: (E)-1-[(5-nitro-2-fur­yl)methyl­idene­amino]­imidazolidine-2,4-dione} is not only used for the treatment of urinary tract infections, but also illegally applied as an animal food additive. Since derivatives of 2,6-diamino­pyridine might serve as artificial receptors for its recognition, we crystallized one potential drug–receptor complex, nitro­furan­toin–2,6-diacetamido­pyridine (1/1), C₈H₆N₄O₅·C₉H₁₁N₃O₂, (I·II). It is characterized by one N—H...N and two N—H...O hydrogen bonds and confirms a previous NMR study. During the crystallization screening, several new pseudopolymorphs of both components were obtained, namely a nitro­furan­toin dimethyl sulfoxide monosolvate, C₈H₆N₄O₅·C₂H₆OS, (Ia), a nitro­furan­toin dimethyl sulfoxide hemisolvate, C₈H₆N₄O₅·0.5C₂H₆OS, (Ib), two nitro­furan­toin dimethyl­acetamide monosolvates, C₈H₆N₄O₅·C₄H₉NO, (Ic) and (Id), and a nitro­furan­toin dimethyl­acetamide disolvate, C₈H₆N₄O₅·2C₄H₉NO, (Ie), as well as a 2,6-diacetamido­pyridine dimethyl­formamide monosolvate, C₉H₁₁N₃O₂·C₃H₇NO, (IIa). Of these, (Ia), (Ic) and (Id) were formed during cocrystallization attempts with 1-(4-fluorophenyl)biguanide hydrochloride. Obviously nitro­furan­toin prefers the higher-energy conformation in the crystal structures, which all exhibit N—H...O and C—H...O hydrogen-bond inter­actions. The latter are especially important for the crystal packing. 2,6-Diacetamido­pyridine shows some conformational flexibility depending on the hydrogen-bond pattern.

S1. Comment

Nitrofurantoin is an antibacterial drug used for the treatment of urinary tract infections. It is reduced by bacterial flavoproteins to reactive intermediates, which inhibit the processes of protein synthesis, aerobic energy metabolism as well as DNA, RNA and cell wall synthesis (Cadwallader & Jun, 1976). The resistance of E. coli to other antibiotics has led to an increased interest in this drug in spite of its severe side effects (Cunha, 2006). In many countries, it is illegally applied as an animal food additive, which can further be passed to humans through the food chain and cause plenty of diseases. Since the present quantification of nitrofurantoin is time-consuming and costly, diaminopyridine derivatives are developed as artificial receptors for its recognition. The drug–receptor complex is characterized by one N—H···N and two N—H···O hydrogen bonds and has been examined by NMR spectroscopy (Athikomrattanakul et al., 2009).

A study of the Cambridge Structural Database (CSD, Version 5.31 of November 2009, plus three updates; Allen, 2002) revealed that similar hydrogen-bond patterns are observed in cocrystals of 2,6-diaminopyridine derivatives and six-membered ring compounds with complementary functional groups [CSD refcodes: DOPCUG (Feibush et al., 1986), FODTIB (Hamilton & Van Engen, 1987), MAWPUW (Li et al., 2005), VABVID and VABVOJ (Muehldorf et al., 1988), XESSAQ (Spange et al., 2006)]. Since no such cocrystal with five-membered ring compounds has been reported, we cocrystallized nitrofurantoin and 2,6-diacetaminopyridine. In addition to the desired cocrystal, (I.II), five pseudopolymorphs of nitrofurantoin crystallized during the various cocrystallization experiments: a dimethyl sulfoxide solvate, (Ia), a dimethyl sulfoxide hemisolvate, (Ib), two dimethylacetamide solvates, (Ic) and (Id), and a dimethylacetamide disolvate, (Ie). Furthermore, a 2,6-diacetaminopyridine dimethylformamide solvate, (II), was obtained.

Compounds (Ia) and (Ib) formed during cocrystallization attempts from dimethyl sulfoxide (DMSO). (Ia) crystallized in the monoclinic space group P2₁/c with one nitrofurantoin and one DMSO molecule in the asymmetric unit. Both molecules are linked by an N—H···O hydrogen bond (Fig. 1). C—H···O interactions between nitrofurantoin molecules lead to ribbons running along the a axis, which are further stabilized by van der Waals interactions to a herringbone pattern (Fig. 2). Compound (Ib) crystallized in the monoclinic space group C2/c as a hemisolvate. The DMSO molecule lies on a twofold axis with the S atom disordered over two positions (Fig. 3). The packing of (Ib) shows zigzag chains of C—H···O-bonded nitrofurantoin molecules running along the a axis (Fig. 4).

Crystallization attempts from dimethylacetamide (DMAC) yielded another three nitrofurantoin solvates, (Ic), (Id) and (Ie). (Ic) and (Id) crystallized with one nitrofurantoin and one DMAC molecule in the asymmetric unit (Figs. 5 and 6). In both structures, the DMAC molecule is disordered over two sites with all non-hydrogen atoms of these two sites in a common plane (r.m.s. deviation = 0.024 Å). (Ic) crystallized in the triclinic space group P1, (Id) in the monoclinic space group P2₁/c. A similar hydrogen-bond pattern is observed: the nitrofurantoin molecules are linked to each other by C—H···O and to the solvent molecules by N—H···O interactions. However, the packing motifs of the two polymorphs are quite different. Nitrofurantoin and solvent molecules form ribbons parallel to the (0 2 3) plane in (Ic) and zigzag chains running along the b axis in (Id) (Figs. 7 and 8). In structure (Ie), which crystallized in the monoclinic space group P2₁/c, there are two independent solvent molecules (Fig. 9). Again, each DMAC molecule is disordered over two sites with a planar arrangement of all non-hydrogen atoms (r.m.s. deviation = 0.024 and 0.038 Å, respectively). The nitrofurantoin molecules are linked to one of these by an N—H···O and to the other one by a C—H···O hydrogen bond. The packing shows layers parallel to the (5 0 2) plane (Fig. 10).

In the five pseudopolymorphs, (Ia)–(Ie), the configuration of nitrofurantoin with respect to the C7═N6 double bond is E with C7–H pointing towards the methylene group of the imidazolidinedione ring. The dihedral angle between the planes through the two rings varies from 5.9 (1) to 12.4 (1)°. Since also the nitro group is rotated by less than 10° with respect to the furan ring, the molecules are almost planar (Table 10). Due to the rotatable C7—C8 bond, nitrofurantoin can adopt two forms: an antiperiplanar conformation between N6 and the furan O9 atom [as in (Ib)] and a synperiplanar conformation (observed in the other four pseudopolymorphs). According to an ab initio energy calculation with geometry optimization [program Gaussian; basis set: RHF/6–31+G(d); Frisch et al., 2004], the synperiplanar conformation is by 11.8 kJ mol^-1 less stable than the antiperiplanar one. Since high-energy conformers are rarely observed in crystal structures (Weng et al., 2008), we examined all five entries of nitrofurantoin in the CSD [refcodes: HAXBUD, HAXBUD01 (Pienaar et al., 1993a), LABJON (Bertolasi et al., 1993), LABJON01 and LABJON02 (Pienaar et al., 1993b)], which confirmed that apparently the higher-energy conformer is preferred in the solid state. A detailed analysis with our force-field program MOMO (Wagner et al., 2009), which also clearly favoured the antiperiplanar conformation, yielded that the energy difference is caused by electrostatic interactions. A closer examination of the molecular charge distribution calculated by Gaussian shows that the positive and negative charges are equally distributed in the antiperiplanar conformation, while in the synperiplanar one the molecule has positive and negative sides (Fig. 11). This may promote a more compact crystal packing, which would explain why the less stable conformer is favoured in the solid phase.

During the preparation of the nitrofurantoin receptor 2,6-diacetaminopyridine it crystallized as a dimethylformamide (DMF) solvate, (II), in the monoclinic space group P2₁/c. Both methyl groups of the 2,6-diacetaminopyridine molecule show rotational disorder and are antiperiplanar to the pyridine ring atoms. Thus the two N—H bonds are directed to the same side as the pyridine N atom (Fig. 12). The 2,6-diacetaminopyridine and the DMF molecule are connected by an N—H···O hydrogen bond from one amide group. These entities form zigzag chains along the c axis stabilized by further N—H···O bonds between the other amide groups (Fig. 13). Similar conformations are observed in the crystal structures of solvent-free 2,6-diacetaminopyridine [refcodes: DOPDAN (Feibush et al., 1986) and DOPDAN01 (Mahapatra et al., 2009)].

The desired complex (I.II) crystallized in the monoclinic space group P2₁/n, with nitrofurantoin and 2,6-diacetaminopyridine connected by one N—H···N and two N—H···O bonds (Fig. 14). As in (Ib), the nitrofurantoin molecule adopts the antiperiplanar conformation as well as the usual E configuration of the C═N double bond. The nitro group and the furan ring are coplanar and the planes through the furan and the imidazolidinedione moiety form a dihedral angle of 9.0 (1)°. Similar to (II), the carbonyl O atoms of the 2,6-diacetaminopyridine molecule point away from the pyridine N atom. One of the amide groups is coplanar with the pyridine ring, while the other one encloses a dihedral angle of 16.7 (1)° with it. The crystal packing shows layers parallel to the (1 0 3) plane, which are stabilized by C—H···O interactions between both components (Fig. 15).

Nitrofurantoin forms an N—H···O and a C—H···O hydrogen bond in all (pseudo)polymorphs. Interestingly, the N—H···O bond connects two nitrofurantoin molecules only in the solvent-free forms (LABJON, LABJON01 and LABJON02); in the solvates [(Ia)–(Ie), HAXBUD, HAXBUD01], it is formed to the solvent molecule. The C—H···O interaction (always with participation of the C—H bond of the hydrazone moiety N—N═C—H) usually connects two nitrofurantoin molecules and thus plays a significant role for the crystal packing, also for that of the complex (I.II). Even though its molecular structure in solvent-free forms and the dimethylformamide solvate (II) is very similar, 2,6-diacetaminopyridine shows some conformational flexibility. The dihedral angle between the planes through the amide groups and the pyridine ring varies from 2.8 to 33.4° depending on the hydrogen-bond interactions. In the cocrystal (I.II), the hydrogen-bonded complexes are further linked by C—H···O interactions to the amide. As a result of that, the 2,6-diacetaminopyridine molecule is not planar. Altogether, since no crystal structure of a complex between nitrofurantoin and a 2,6-diaminopyridine derivative has yet been published, the cocrystal (I.II) confirms the NMR study (Athikomrattanakul et al., 2009) of this drug–receptor complex.

Related literature

For related literature, see: Allen (2002); Athikomrattanakul et al. (2009); Bertolasi et al. (1993); Cadwallader & Jun (1976); Cunha (2006); Feibush et al. (1986); Frisch et al. (2004); Hamilton & Van Engen (1987); Li et al. (2005); Mahapatra et al. (2009); Muehldorf et al. (1988); Pienaar et al. (1993a, 1993b); Spange et al. (2006); Wagner et al. (2009); Weng et al. (2008).

S2. Experimental

Single crystals of (Ia), (Ic) and (Id) were obtained by cocrystallization of commercially available nitrofurantoin with 1-(4-fluorophenyl)biguanide hydrochloride (Table 8). Solvent evaporation experiments with mixtures of nitrofurantoin and 2,6-diacetaminopyridine yielded (Ib), (Ie) and the cocrystal, (I.II) (Table 9).

For the preparation of compound (II), 2,6-diaminopyridine (5 g, 0.046 mol) was added to a solution of acetic acid anhydride (10.4 ml, 0.055 mol) in 1,4-dioxane (100 ml) under a nitrogen atmosphere. The reaction mixture was heated at reflux for 24 h. After cooling to room temperature, the solvent was removed using a rotary evaporator. Unreacted 2,6-diaminopyridine and acetic acid anhydride were rinsed away with water. 11.5 mg of 2,6-diacetaminopyridine dissolved in dimethylformamide (200 µl) at 323 K yielded (II).

S3. Refinement

Crystals (Ia), (Id) and (I.II) show R_int-values higher than 0.100: 0.176 (Ia), 0.147 (Id) and 0.138 (I.II), although the data sets were collected with high redundancy: 6.52 (Ia), 6.32 (Id) and 8.98 (I.II). (Ia) and (Id) did not diffract very strongly [R_σ values: 0.106 (Ia) and 0.099 (Id)], but there is no obvious reason for (I.II). However, all other important quality criteria are satisfied.

The H atoms, except those bonded to disordered solvent atoms, were initially located by difference Fourier synthesis. Subsequently, H atoms bonded to C atoms were refined using a riding model, with methyl C—H = 0.98 Å, secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å and with U_iso(H) = 1.5U_eq(C) for methyl H or 1.2U_eq(C) for secondary and aromatic H. H atoms bonded to N atoms were refined isotropically.

In (Ib), the O atom of the dimethyl sulfoxide lies on a twofold axis so that the S atom is disordered. In (Ic), (Id) and (Ie), all solvent atoms except O are disordered over two positions, but the disordered methyl C atoms coincide pairwise thus forming a rectangular arrangement together with the O atom. The site-occupation factors for the major occupied orientations are 0.646 (7) in (Ic), 0.53 (1) in (Id), 0.926 (5) and 0.882 (6) in (Ie). For the minor occupied orientations of both solvent molecules in (Ie), similarity restraints were applied and the carbonyl C and the N atoms were refined isotropically.

In (II), the methyl groups of 2,6-diacetaminopyridine are rotationally disordered over two positions, with site-occupation factors of 0.58 (5) and 0.66 (2) for the major occupied orientations.

Computing details

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. A perspective view of (Ia), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates the N—H···O hydrogen bond.
	Fig. 2. A packing diagram for (Ia). N—H···O and C—H···O hydrogen bonds are shown as dashed lines.
	Fig. 3. A perspective view of (Ib), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates the N—H···O hydrogen bond. The dimethyl sulfoxide solvent molecule lies on a twofold axis; only one of the two disordered positions is shown.
	Fig. 4. A packing diagram for (Ib). N—H···O and C—H···O hydrogen bonds are shown as dashed lines. Only one site of the disordered dimethyl sulfoxide is shown.
	Fig. 5. A perspective view of (Ic), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates the N—H···O hydrogen bond. The dimethylacetamide solvent molecule is disordered; only the major occupied site is shown.
	Fig. 6. A perspective view of (Id), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates the N—H···O hydrogen bond. The dimethylacetamide solvent molecule is disordered; only the major occupied site is shown.
	Fig. 7. A partial packing diagram for (Ic). N—H···O and C—H···O hydrogen bonds are shown as dashed lines. The minor occupied site of the dimethylacetamide solvent molecules has been omitted.
	Fig. 8. A partial packing diagram for (Id). N—H···O and C—H···O hydrogen bonds are shown as dashed lines. The minor occupied site of the dimethylacetamide solvent molecules has been omitted.
	Fig. 9. A perspective view of (Ie), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed lines indicate hydrogen bonds. The dimethylacetamide solvent molecules are disordered; only the major occupied sites are shown.
	Fig. 10. A partial packing diagram for (Ie). N—H···O and C—H···O hydrogen bonds are shown as dashed lines. The minor occupied sites of the dimethylacetamide solvent molecules have been omitted.
	Fig. 11. (a) The molecular charge distribution of the antiperiplanar conformer of nitrofurantoin. (In the electronic version of the paper, regions of high relative negative charge are red and those of high relative positive charge are blue.) The electrostatic potential was calculated on an isosurface at 0.0004 e/b^3; the colour scale ranges from -0.07 to +0.07 h (e: elementary charge; b: bohr, the atomic unit of length; h: hartree, the atomic unit of energy). (b) The molecular charge distribution of the synperiplanar conformer of nitrofurantoin. (In the electronic version of the paper, regions of high relative negative charge are red and those of high relative positive charge are blue.) The electrostatic potential was calculated on an isosurface at 0.0004 e/b^3; the colour scale ranges from -0.07 to +0.07 h (e: elementary charge; b: bohr, the atomic unit of length; h: hartree, the atomic unit of energy). (c) The colour scale for the molecular charge distribution.
	Fig. 12. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates the N—H···O hydrogen bond. The rotational disorder of the methyl groups is not shown.
	Fig. 13. A partial packing diagram for (II). Hydrogen bonds are shown as dashes lines.
	Fig. 14. A perspective view of (I.II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed lines indicate hydrogen bonds.
	Fig. 15. A partial packing diagram for (I.II). N—H···O, N—H···N and C—H···O hydrogen bonds are shown as dashed lines.

(Ia) (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione dimethyl sulfoxide monosolvate

Crystal data

C8H6N4O5·C2H6OS	F(000) = 656
Mr = 316.30	Dx = 1.520 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6257 (4) Å	Cell parameters from 5085 reflections
b = 26.488 (2) Å	θ = 3.5–25.8°
c = 8.0032 (5) Å	µ = 0.27 mm^−1
β = 100.347 (5)°	T = 173 K
V = 1381.73 (16) Å^3	Block, yellow
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer	2437 independent reflections
Radiation source: fine-focus sealed tube	1588 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.176
ω scans	θmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −7→7
Tmin = 0.900, Tmax = 0.948	k = −31→31
15878 measured reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0422P)^2] where P = (Fo^2 + 2Fc^2)/3
2437 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.53 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.7086 (4)	0.37863 (10)	0.4536 (4)	0.0263 (6)
H1	0.808 (6)	0.3612 (14)	0.417 (5)	0.031 (10)*
C2	0.7313 (5)	0.41820 (12)	0.5674 (4)	0.0255 (7)
O21	0.8912 (3)	0.43666 (10)	0.6389 (3)	0.0374 (6)
N3	0.5355 (4)	0.43282 (10)	0.5848 (4)	0.0247 (6)
C4	0.3781 (5)	0.40286 (13)	0.4784 (4)	0.0283 (8)
H4A	0.2874	0.4242	0.3953	0.034*
H4B	0.2939	0.3839	0.5475	0.034*
C5	0.5071 (5)	0.36756 (13)	0.3910 (5)	0.0292 (8)
O51	0.4452 (4)	0.33599 (10)	0.2849 (4)	0.0421 (7)
N6	0.5106 (4)	0.47279 (9)	0.6863 (3)	0.0230 (6)
C7	0.3239 (5)	0.48193 (12)	0.7029 (4)	0.0240 (7)
H7	0.2155	0.4614	0.6457	0.029*
C8	0.2799 (4)	0.52292 (12)	0.8074 (4)	0.0240 (7)
O9	0.4395 (3)	0.55309 (8)	0.8855 (3)	0.0239 (5)
C10	0.3505 (5)	0.58815 (12)	0.9710 (4)	0.0278 (8)
C11	0.1459 (5)	0.58211 (13)	0.9555 (4)	0.0300 (8)
H11	0.0531	0.6021	1.0049	0.036*
C12	0.1002 (5)	0.53948 (12)	0.8496 (4)	0.0276 (8)
H12	−0.0315	0.5249	0.8140	0.033*
N13	0.4882 (5)	0.62297 (11)	1.0693 (4)	0.0341 (7)
O14	0.6726 (4)	0.61732 (10)	1.0802 (4)	0.0434 (7)
O15	0.4070 (4)	0.65681 (10)	1.1426 (4)	0.0463 (7)
O1A	1.0023 (3)	0.31445 (9)	0.3776 (3)	0.0315 (6)
S2A	1.01025 (13)	0.28756 (3)	0.21177 (11)	0.0271 (2)
C3A	1.1797 (6)	0.23559 (14)	0.2655 (5)	0.0391 (9)
H3A1	1.3190	0.2481	0.3061	0.059*
H3A2	1.1787	0.2144	0.1649	0.059*
H3A3	1.1347	0.2156	0.3550	0.059*
C4A	0.7764 (6)	0.25235 (14)	0.1625 (5)	0.0383 (9)
H4A1	0.7651	0.2296	0.2570	0.058*
H4A2	0.7764	0.2325	0.0591	0.058*
H4A3	0.6596	0.2757	0.1446	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0224 (14)	0.0276 (15)	0.0298 (16)	−0.0008 (12)	0.0070 (11)	−0.0046 (13)
C2	0.0246 (16)	0.0270 (17)	0.0261 (18)	−0.0005 (14)	0.0077 (14)	0.0016 (15)
O21	0.0181 (12)	0.0494 (16)	0.0444 (16)	−0.0073 (11)	0.0047 (11)	−0.0165 (13)
N3	0.0180 (12)	0.0218 (13)	0.0341 (16)	−0.0031 (10)	0.0044 (11)	−0.0074 (12)
C4	0.0221 (16)	0.0278 (18)	0.035 (2)	−0.0033 (13)	0.0041 (14)	−0.0080 (15)
C5	0.0236 (16)	0.0275 (18)	0.037 (2)	−0.0052 (14)	0.0054 (14)	−0.0039 (16)
O51	0.0342 (14)	0.0426 (16)	0.0507 (17)	−0.0113 (12)	0.0109 (12)	−0.0238 (14)
N6	0.0246 (14)	0.0198 (13)	0.0252 (15)	−0.0002 (11)	0.0058 (11)	−0.0008 (11)
C7	0.0216 (16)	0.0198 (15)	0.0302 (19)	−0.0030 (12)	0.0032 (13)	0.0004 (14)
C8	0.0203 (15)	0.0217 (16)	0.0287 (18)	0.0006 (12)	0.0010 (13)	0.0030 (14)
O9	0.0216 (11)	0.0206 (11)	0.0287 (13)	−0.0001 (9)	0.0026 (10)	−0.0045 (10)
C10	0.0323 (18)	0.0254 (18)	0.0257 (18)	0.0040 (13)	0.0055 (14)	−0.0011 (15)
C11	0.0325 (18)	0.0292 (18)	0.0297 (19)	0.0067 (14)	0.0096 (15)	0.0020 (15)
C12	0.0236 (17)	0.0260 (18)	0.033 (2)	0.0037 (13)	0.0054 (14)	0.0056 (15)
N13	0.0414 (18)	0.0266 (16)	0.0345 (18)	0.0015 (13)	0.0069 (13)	−0.0039 (14)
O14	0.0334 (15)	0.0403 (16)	0.0531 (18)	−0.0056 (11)	−0.0012 (12)	−0.0062 (13)
O15	0.0623 (17)	0.0329 (15)	0.0445 (16)	0.0024 (13)	0.0120 (14)	−0.0132 (13)
O1A	0.0326 (13)	0.0329 (13)	0.0306 (14)	0.0056 (10)	0.0097 (10)	−0.0077 (11)
S2A	0.0302 (4)	0.0244 (4)	0.0286 (4)	0.0028 (4)	0.0105 (3)	0.0009 (4)
C3A	0.043 (2)	0.0307 (19)	0.043 (2)	0.0124 (16)	0.0065 (17)	−0.0025 (18)
C4A	0.040 (2)	0.036 (2)	0.042 (2)	−0.0081 (16)	0.0148 (17)	−0.0073 (18)

Geometric parameters (Å, º)

N1—C5	1.371 (4)	C10—C11	1.348 (5)
N1—C2	1.379 (4)	C10—N13	1.430 (4)
N1—H1	0.89 (4)	C11—C12	1.412 (5)
C2—O21	1.213 (4)	C11—H11	0.9500
C2—N3	1.384 (4)	C12—H12	0.9500
N3—N6	1.362 (4)	N13—O14	1.218 (4)
N3—C4	1.457 (4)	N13—O15	1.245 (4)
C4—C5	1.520 (5)	O1A—S2A	1.516 (2)
C4—H4A	0.9900	S2A—C3A	1.780 (3)
C4—H4B	0.9900	S2A—C4A	1.791 (4)
C5—O51	1.209 (4)	C3A—H3A1	0.9800
N6—C7	1.290 (4)	C3A—H3A2	0.9800
C7—C8	1.432 (4)	C3A—H3A3	0.9800
C7—H7	0.9500	C4A—H4A1	0.9800
C8—O9	1.382 (4)	C4A—H4A2	0.9800
C8—C12	1.366 (4)	C4A—H4A3	0.9800
O9—C10	1.351 (4)
C5—N1—C2	112.8 (3)	C11—C10—N13	131.2 (3)
C5—N1—H1	120 (2)	O9—C10—N13	115.4 (3)
C2—N1—H1	128 (2)	C10—C11—C12	104.7 (3)
O21—C2—N3	126.5 (3)	C10—C11—H11	127.6
O21—C2—N1	126.9 (3)	C12—C11—H11	127.6
N3—C2—N1	106.6 (3)	C8—C12—C11	107.6 (3)
N6—N3—C2	119.6 (2)	C8—C12—H12	126.2
N6—N3—C4	128.4 (2)	C11—C12—H12	126.2
C2—N3—C4	112.0 (3)	O14—N13—O15	124.5 (3)
N3—C4—C5	101.6 (2)	O14—N13—C10	119.5 (3)
N3—C4—H4A	111.4	O15—N13—C10	115.9 (3)
C5—C4—H4A	111.4	O1A—S2A—C3A	105.77 (17)
N3—C4—H4B	111.4	O1A—S2A—C4A	105.81 (16)
C5—C4—H4B	111.4	C3A—S2A—C4A	97.69 (19)
H4A—C4—H4B	109.3	S2A—C3A—H3A1	109.5
O51—C5—N1	126.1 (3)	S2A—C3A—H3A2	109.5
O51—C5—C4	126.9 (3)	H3A1—C3A—H3A2	109.5
N1—C5—C4	106.9 (3)	S2A—C3A—H3A3	109.5
C7—N6—N3	115.4 (3)	H3A1—C3A—H3A3	109.5
N6—C7—C8	120.1 (3)	H3A2—C3A—H3A3	109.5
N6—C7—H7	119.9	S2A—C4A—H4A1	109.5
C8—C7—H7	119.9	S2A—C4A—H4A2	109.5
O9—C8—C12	109.4 (3)	H4A1—C4A—H4A2	109.5
O9—C8—C7	118.9 (3)	S2A—C4A—H4A3	109.5
C12—C8—C7	131.7 (3)	H4A1—C4A—H4A3	109.5
C10—O9—C8	105.0 (2)	H4A2—C4A—H4A3	109.5
C11—C10—O9	113.3 (3)
C5—N1—C2—O21	−178.1 (3)	N6—C7—C8—O9	1.8 (5)
C5—N1—C2—N3	2.0 (4)	N6—C7—C8—C12	−177.9 (3)
O21—C2—N3—N6	2.4 (5)	C12—C8—O9—C10	−1.2 (3)
N1—C2—N3—N6	−177.7 (3)	C7—C8—O9—C10	179.0 (3)
O21—C2—N3—C4	179.3 (3)	C8—O9—C10—C11	1.0 (4)
N1—C2—N3—C4	−0.8 (4)	C8—O9—C10—N13	177.5 (3)
N6—N3—C4—C5	176.1 (3)	O9—C10—C11—C12	−0.4 (4)
C2—N3—C4—C5	−0.5 (4)	N13—C10—C11—C12	−176.1 (3)
C2—N1—C5—O51	177.0 (4)	O9—C8—C12—C11	1.0 (4)
C2—N1—C5—C4	−2.3 (4)	C7—C8—C12—C11	−179.2 (3)
N3—C4—C5—O51	−177.7 (4)	C10—C11—C12—C8	−0.4 (4)
N3—C4—C5—N1	1.6 (4)	C11—C10—N13—O14	170.7 (4)
C2—N3—N6—C7	−176.1 (3)	O9—C10—N13—O14	−5.0 (5)
C4—N3—N6—C7	7.5 (5)	C11—C10—N13—O15	−7.4 (5)
N3—N6—C7—C8	179.7 (3)	O9—C10—N13—O15	176.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1A	0.89 (4)	1.86 (4)	2.733 (4)	167 (3)
C7—H7···O21^i	0.95	2.24	3.065 (4)	145

Symmetry code: (i) x−1, y, z.

(Ib) (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione dimethyl sulfoxide hemisolvate

Crystal data

C8H6N4O5·0.5(C2H6OS)	F(000) = 1144
Mr = ?	Dx = 1.633 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.1710 (11) Å	Cell parameters from 10186 reflections
b = 13.7985 (8) Å	θ = 3.6–26.1°
c = 10.3465 (8) Å	µ = 0.22 mm^−1
β = 102.358 (6)°	T = 173 K
V = 2255.2 (3) Å^3	Block, yellow
Z = 8	0.50 × 0.40 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer	2116 independent reflections
Radiation source: fine-focus sealed tube	1806 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
ω scans	θmax = 25.6°, θmin = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −19→19
Tmin = 0.896, Tmax = 0.957	k = −16→16
13781 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0611P)^2 + 0.1688P] where P = (Fo^2 + 2Fc^2)/3
2116 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.55503 (9)	0.28434 (10)	0.47191 (13)	0.0248 (3)
H1	0.5384 (16)	0.2546 (17)	0.399 (3)	0.049 (6)*
C2	0.56931 (10)	0.23377 (11)	0.59100 (15)	0.0223 (3)
O21	0.56260 (9)	0.14817 (8)	0.60474 (11)	0.0333 (3)
N3	0.59366 (9)	0.30307 (9)	0.68891 (12)	0.0230 (3)
C4	0.59851 (11)	0.39981 (11)	0.63492 (15)	0.0249 (4)
H4A	0.6569	0.4258	0.6582	0.030*
H4B	0.5596	0.4453	0.6661	0.030*
C5	0.57099 (10)	0.38098 (12)	0.48737 (15)	0.0251 (3)
O51	0.56544 (8)	0.44117 (9)	0.39996 (11)	0.0365 (3)
N6	0.61420 (8)	0.27458 (9)	0.81746 (12)	0.0221 (3)
C7	0.64003 (10)	0.34106 (11)	0.90363 (14)	0.0228 (3)
H7	0.6438	0.4067	0.8780	0.027*
C8	0.66312 (10)	0.31228 (11)	1.04115 (14)	0.0221 (3)
O9	0.69640 (7)	0.38476 (8)	1.12747 (10)	0.0243 (3)
C10	0.71209 (10)	0.34230 (12)	1.24842 (14)	0.0236 (3)
C11	0.69100 (11)	0.24745 (12)	1.24310 (16)	0.0269 (4)
H11	0.6963	0.2035	1.3150	0.032*
C12	0.65936 (10)	0.22773 (12)	1.10748 (15)	0.0267 (4)
H12	0.6393	0.1671	1.0698	0.032*
N13	0.74641 (9)	0.40287 (10)	1.35737 (13)	0.0270 (3)
O14	0.76313 (8)	0.48756 (9)	1.33718 (11)	0.0331 (3)
O15	0.75653 (8)	0.36511 (10)	1.46809 (11)	0.0367 (3)
O1A	0.5000	0.16833 (11)	0.2500	0.0283 (4)
S2A	0.52129 (5)	0.06598 (5)	0.19909 (7)	0.0209 (2)	0.50
C3A	0.42509 (12)	0.00521 (12)	0.15938 (17)	0.0328 (4)
H3AA	0.4097	−0.0598	0.1836	0.049*	0.50
H3AB	0.3738	0.0413	0.1194	0.049*	0.50
H3AC	0.4619	0.0003	0.0955	0.049*	0.50
H3AD	0.4341	−0.0597	0.1265	0.049*	0.50
H3AE	0.4011	0.0000	0.2383	0.049*	0.50
H3AF	0.3860	0.0413	0.0905	0.049*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0287 (7)	0.0287 (7)	0.0149 (6)	−0.0048 (6)	0.0001 (5)	−0.0006 (5)
C2	0.0244 (8)	0.0246 (8)	0.0179 (7)	−0.0015 (6)	0.0045 (6)	−0.0009 (6)
O21	0.0521 (8)	0.0220 (6)	0.0249 (6)	−0.0049 (5)	0.0062 (5)	−0.0017 (5)
N3	0.0326 (7)	0.0206 (6)	0.0139 (6)	−0.0012 (5)	0.0008 (5)	0.0017 (5)
C4	0.0331 (9)	0.0211 (8)	0.0179 (7)	−0.0007 (6)	0.0001 (6)	0.0027 (6)
C5	0.0250 (8)	0.0284 (8)	0.0194 (7)	−0.0014 (6)	−0.0007 (6)	0.0045 (6)
O51	0.0467 (8)	0.0360 (7)	0.0224 (6)	−0.0034 (6)	−0.0026 (5)	0.0118 (5)
N6	0.0262 (7)	0.0245 (7)	0.0144 (6)	0.0012 (5)	0.0017 (5)	0.0030 (5)
C7	0.0276 (8)	0.0224 (7)	0.0176 (7)	0.0005 (6)	0.0029 (6)	0.0014 (6)
C8	0.0232 (8)	0.0254 (8)	0.0170 (7)	0.0009 (6)	0.0024 (6)	−0.0024 (6)
O9	0.0306 (6)	0.0253 (6)	0.0150 (5)	0.0010 (4)	0.0006 (4)	0.0006 (4)
C10	0.0255 (8)	0.0302 (8)	0.0139 (7)	0.0026 (6)	0.0015 (6)	0.0020 (6)
C11	0.0292 (8)	0.0312 (8)	0.0192 (7)	0.0022 (7)	0.0028 (6)	0.0059 (6)
C12	0.0313 (9)	0.0263 (8)	0.0215 (8)	−0.0014 (7)	0.0033 (6)	0.0007 (6)
N13	0.0261 (7)	0.0342 (8)	0.0185 (7)	0.0038 (6)	0.0000 (5)	−0.0004 (5)
O14	0.0387 (7)	0.0295 (6)	0.0277 (6)	0.0009 (5)	−0.0006 (5)	−0.0034 (5)
O15	0.0433 (8)	0.0480 (8)	0.0149 (6)	−0.0020 (6)	−0.0028 (5)	0.0037 (5)
O1A	0.0396 (10)	0.0186 (8)	0.0236 (8)	0.000	−0.0004 (7)	0.000
S2A	0.0270 (4)	0.0197 (4)	0.0152 (3)	−0.0005 (3)	0.0031 (3)	−0.0002 (3)
C3A	0.0358 (9)	0.0255 (8)	0.0317 (9)	−0.0012 (7)	−0.0051 (7)	0.0008 (7)

Geometric parameters (Å, º)

N1—C5	1.361 (2)	C11—C12	1.413 (2)
N1—C2	1.3916 (19)	C11—H11	0.9500
N1—H1	0.85 (3)	C12—H12	0.9500
C2—O21	1.1975 (19)	N13—O14	1.2274 (19)
C2—N3	1.387 (2)	N13—O15	1.2371 (18)
N3—N6	1.3582 (17)	O1A—S2A^i	1.5710 (15)
N3—C4	1.4556 (19)	O1A—S2A	1.5710 (15)
C4—C5	1.518 (2)	S2A—S2A^i	1.3763 (15)
C4—H4A	0.9900	S2A—C3A	1.7374 (19)
C4—H4B	0.9900	S2A—C3A^i	1.7482 (18)
C5—O51	1.2170 (19)	S2A—H3AC	1.5663
N6—C7	1.285 (2)	C3A—S2A^i	1.7482 (18)
C7—C8	1.447 (2)	C3A—H3AA	0.9782
C7—H7	0.9500	C3A—H3AB	0.9800
C8—C12	1.362 (2)	C3A—H3AC	0.9817
C8—O9	1.3718 (18)	C3A—H3AD	0.9797
O9—C10	1.3557 (18)	C3A—H3AE	0.9781
C10—C11	1.351 (2)	C3A—H3AF	0.9807
C10—N13	1.418 (2)
C5—N1—C2	113.31 (13)	S2A^i—O1A—S2A	51.96 (7)
C5—N1—H1	126.3 (16)	S2A^i—S2A—O1A	64.02 (4)
C2—N1—H1	120.4 (16)	S2A^i—S2A—C3A	67.16 (8)
O21—C2—N1	126.70 (14)	O1A—S2A—C3A	105.30 (7)
O21—C2—N3	127.73 (14)	S2A^i—S2A—C3A^i	66.33 (8)
N1—C2—N3	105.57 (13)	O1A—S2A—C3A^i	104.80 (7)
N6—N3—C2	119.17 (12)	C3A—S2A—C3A^i	103.01 (11)
N6—N3—C4	128.26 (12)	S2A^i—S2A—H3AC	100.9
C2—N3—C4	112.46 (12)	O1A—S2A—H3AC	127.1
N3—C4—C5	101.57 (12)	C3A^i—S2A—H3AC	114.7
N3—C4—H4A	111.5	S2A—C3A—S2A^i	46.51 (6)
C5—C4—H4A	111.5	S2A—C3A—H3AA	130.3
N3—C4—H4B	111.5	S2A^i—C3A—H3AA	109.4
C5—C4—H4B	111.5	S2A—C3A—H3AB	119.2
H4A—C4—H4B	109.3	S2A^i—C3A—H3AB	109.4
O51—C5—N1	126.82 (15)	H3AA—C3A—H3AB	109.6
O51—C5—C4	126.12 (15)	S2A—C3A—H3AC	63.4
N1—C5—C4	107.06 (13)	S2A^i—C3A—H3AC	109.5
C7—N6—N3	116.61 (13)	H3AA—C3A—H3AC	109.5
N6—C7—C8	117.61 (14)	H3AB—C3A—H3AC	109.3
N6—C7—H7	121.2	S2A—C3A—H3AD	109.4
C8—C7—H7	121.2	S2A^i—C3A—H3AD	130.2
C12—C8—O9	110.50 (13)	H3AA—C3A—H3AD	46.8
C12—C8—C7	134.49 (14)	H3AB—C3A—H3AD	119.6
O9—C8—C7	115.01 (13)	H3AC—C3A—H3AD	63.1
C10—O9—C8	104.81 (12)	S2A—C3A—H3AE	109.4
O9—C10—C11	112.68 (13)	S2A^i—C3A—H3AE	63.3
O9—C10—N13	116.31 (13)	H3AA—C3A—H3AE	63.3
C11—C10—N13	131.01 (14)	H3AB—C3A—H3AE	86.5
C10—C11—C12	105.17 (13)	H3AC—C3A—H3AE	164.2
C10—C11—H11	127.4	H3AD—C3A—H3AE	109.7
C12—C11—H11	127.4	S2A—C3A—H3AF	109.4
C8—C12—C11	106.84 (14)	S2A^i—C3A—H3AF	119.4
C8—C12—H12	126.6	H3AA—C3A—H3AF	119.5
C11—C12—H12	126.6	H3AC—C3A—H3AF	86.3
O14—N13—O15	124.63 (14)	H3AD—C3A—H3AF	109.4
O14—N13—C10	119.28 (13)	H3AE—C3A—H3AF	109.6
O15—N13—C10	116.09 (14)
C5—N1—C2—O21	−177.59 (17)	C12—C8—O9—C10	−0.56 (17)
C5—N1—C2—N3	1.74 (18)	C7—C8—O9—C10	179.28 (13)
O21—C2—N3—N6	1.0 (3)	C8—O9—C10—C11	0.27 (17)
N1—C2—N3—N6	−178.34 (13)	C8—O9—C10—N13	−179.27 (13)
O21—C2—N3—C4	177.32 (17)	O9—C10—C11—C12	0.10 (19)
N1—C2—N3—C4	−2.00 (18)	N13—C10—C11—C12	179.55 (16)
N6—N3—C4—C5	177.42 (14)	O9—C8—C12—C11	0.63 (19)
C2—N3—C4—C5	1.48 (17)	C7—C8—C12—C11	−179.16 (17)
C2—N1—C5—O51	178.33 (17)	C10—C11—C12—C8	−0.44 (19)
C2—N1—C5—C4	−0.83 (18)	O9—C10—N13—O14	−2.9 (2)
N3—C4—C5—O51	−179.55 (17)	C11—C10—N13—O14	177.64 (17)
N3—C4—C5—N1	−0.38 (17)	O9—C10—N13—O15	176.39 (13)
C2—N3—N6—C7	176.90 (14)	C11—C10—N13—O15	−3.0 (3)
C4—N3—N6—C7	1.2 (2)	S2A^i—O1A—S2A—C3A	54.48 (8)
N3—N6—C7—C8	−179.37 (13)	S2A^i—O1A—S2A—C3A^i	−53.80 (8)
N6—C7—C8—C12	−5.1 (3)	O1A—S2A—C3A—S2A^i	−52.55 (5)
N6—C7—C8—O9	175.15 (13)	C3A^i—S2A—C3A—S2A^i	57.02 (9)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1A	0.85 (3)	1.94 (3)	2.7841 (16)	171 (2)
C7—H7···O51^ii	0.95	2.49	3.235 (2)	136

Symmetry code: (ii) x, −y+1, z+1/2.

(Ic) (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dion dimethylacetamide monosolvate

Crystal data

C8H6N4O5·C4H9NO	Z = 2
Mr = 325.29	F(000) = 340
Triclinic, P1	Dx = 1.464 Mg m^−3
a = 6.6544 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9842 (6) Å	Cell parameters from 17770 reflections
c = 14.3515 (11) Å	θ = 3.2–26.1°
α = 100.021 (6)°	µ = 0.12 mm^−1
β = 93.566 (6)°	T = 173 K
γ = 99.274 (6)°	Block, colourless
V = 737.85 (10) Å^3	0.30 × 0.30 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer	2111 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.062
Graphite monochromator	θmax = 25.6°, θmin = 3.2°
ω scans	h = −8→8
24053 measured reflections	k = −9→9
2770 independent reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0657P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2770 reflections	Δρmax = 0.28 e Å^−3
232 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (4)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.3323 (2)	0.62290 (18)	0.73950 (10)	0.0296 (3)
H1	0.230 (4)	0.649 (3)	0.7792 (18)	0.065 (7)*
C2	0.2983 (2)	0.4852 (2)	0.66326 (11)	0.0281 (4)
O21	0.13623 (17)	0.39642 (17)	0.63138 (9)	0.0382 (3)
N3	0.4876 (2)	0.47248 (18)	0.63120 (9)	0.0282 (3)
C4	0.6510 (2)	0.6003 (2)	0.68690 (11)	0.0308 (4)
H4A	0.7243	0.6746	0.6469	0.037*
H4B	0.7500	0.5452	0.7199	0.037*
C5	0.5329 (3)	0.7013 (2)	0.75657 (11)	0.0302 (4)
O51	0.60202 (19)	0.82787 (16)	0.81607 (9)	0.0403 (3)
N6	0.5037 (2)	0.34449 (18)	0.55711 (9)	0.0276 (3)
C7	0.6869 (2)	0.3273 (2)	0.53814 (11)	0.0282 (4)
H7	0.8010	0.4026	0.5743	0.034*
C8	0.7176 (2)	0.1933 (2)	0.46184 (11)	0.0285 (4)
O9	0.54888 (17)	0.09676 (15)	0.40652 (7)	0.0298 (3)
C10	0.6247 (3)	−0.0162 (2)	0.34225 (11)	0.0302 (4)
C11	0.8301 (3)	0.0020 (2)	0.35424 (12)	0.0336 (4)
H11	0.9153	−0.0632	0.3178	0.040*
C12	0.8918 (3)	0.1390 (2)	0.43258 (12)	0.0314 (4)
H12	1.0278	0.1845	0.4596	0.038*
N13	0.4754 (2)	−0.1362 (2)	0.27809 (10)	0.0370 (4)
O14	0.2939 (2)	−0.13929 (19)	0.29028 (9)	0.0469 (4)
O15	0.5403 (2)	−0.23311 (18)	0.21488 (9)	0.0504 (4)
O1A	0.0279 (2)	0.65609 (19)	0.85940 (9)	0.0452 (4)
C3A	0.2632 (3)	0.8710 (3)	0.98807 (15)	0.0448 (5)
H3AA	0.2266	0.9795	1.0198	0.067*	0.646 (7)
H3AB	0.3498	0.8937	0.9373	0.067*	0.646 (7)
H3AC	0.3378	0.8212	1.0344	0.067*	0.646 (7)
H3AD	0.3295	0.9546	1.0441	0.067*	0.354 (7)
H3AE	0.3462	0.7810	0.9723	0.067*	0.354 (7)
H3AF	0.2497	0.9302	0.9342	0.067*	0.354 (7)
C5A	−0.0287 (3)	0.8084 (3)	1.10608 (13)	0.0534 (6)
H5AA	−0.1588	0.8341	1.1281	0.080*	0.646 (7)
H5AB	0.0687	0.9164	1.1112	0.080*	0.646 (7)
H5AC	0.0265	0.7345	1.1454	0.080*	0.646 (7)
H5AD	0.0634	0.8976	1.1518	0.080*	0.354 (7)
H5AE	−0.1643	0.8408	1.1008	0.080*	0.354 (7)
H5AF	−0.0397	0.6978	1.1279	0.080*	0.354 (7)
C6A	−0.2580 (3)	0.5867 (3)	0.96691 (16)	0.0438 (5)
H6AA	−0.3728	0.6480	0.9603	0.066*	0.646 (7)
H6AB	−0.2875	0.5068	1.0110	0.066*	0.646 (7)
H6AC	−0.2380	0.5216	0.9047	0.066*	0.646 (7)
H6AD	−0.2665	0.6336	1.0341	0.066*	0.354 (7)
H6AE	−0.3724	0.6118	0.9285	0.066*	0.354 (7)
H6AF	−0.2644	0.4614	0.9583	0.066*	0.354 (7)
C2A	0.0691 (6)	0.7444 (5)	0.9457 (3)	0.0391 (11)	0.646 (7)
N4A	−0.0626 (6)	0.7180 (5)	1.0058 (2)	0.0423 (11)	0.646 (7)
N4B	0.0568 (8)	0.7914 (6)	1.0092 (3)	0.0216 (14)	0.354 (7)
C2B	−0.0598 (8)	0.6682 (6)	0.9361 (3)	0.0151 (15)	0.354 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0264 (7)	0.0314 (8)	0.0296 (7)	0.0049 (6)	0.0033 (6)	0.0015 (6)
C2	0.0256 (9)	0.0318 (9)	0.0272 (8)	0.0069 (7)	0.0006 (6)	0.0054 (7)
O21	0.0225 (6)	0.0410 (7)	0.0452 (7)	0.0034 (6)	−0.0013 (5)	−0.0044 (6)
N3	0.0226 (7)	0.0351 (8)	0.0242 (6)	0.0026 (6)	0.0013 (5)	0.0011 (6)
C4	0.0255 (8)	0.0351 (10)	0.0289 (8)	−0.0008 (7)	−0.0004 (6)	0.0048 (7)
C5	0.0320 (9)	0.0305 (9)	0.0274 (8)	0.0039 (7)	−0.0009 (7)	0.0064 (7)
O51	0.0417 (7)	0.0357 (7)	0.0370 (7)	0.0008 (6)	−0.0033 (5)	−0.0032 (6)
N6	0.0288 (7)	0.0316 (8)	0.0231 (6)	0.0071 (6)	0.0021 (5)	0.0054 (6)
C7	0.0247 (8)	0.0355 (9)	0.0245 (8)	0.0040 (7)	0.0005 (6)	0.0075 (7)
C8	0.0269 (8)	0.0333 (9)	0.0259 (8)	0.0042 (7)	0.0007 (6)	0.0087 (7)
O9	0.0271 (6)	0.0360 (7)	0.0263 (6)	0.0058 (5)	0.0020 (4)	0.0057 (5)
C10	0.0341 (9)	0.0296 (9)	0.0275 (8)	0.0056 (7)	0.0033 (7)	0.0069 (7)
C11	0.0355 (10)	0.0341 (10)	0.0327 (9)	0.0096 (8)	0.0077 (7)	0.0059 (7)
C12	0.0270 (9)	0.0354 (10)	0.0327 (9)	0.0059 (7)	0.0047 (7)	0.0079 (7)
N13	0.0438 (10)	0.0353 (9)	0.0311 (8)	0.0014 (7)	−0.0010 (6)	0.0102 (7)
O14	0.0344 (8)	0.0591 (9)	0.0433 (7)	−0.0036 (6)	−0.0051 (6)	0.0128 (6)
O15	0.0642 (10)	0.0405 (8)	0.0402 (7)	0.0064 (7)	0.0015 (7)	−0.0057 (6)
O1A	0.0425 (8)	0.0622 (9)	0.0309 (7)	0.0205 (7)	0.0056 (6)	−0.0022 (6)
C3A	0.0293 (10)	0.0386 (11)	0.0586 (12)	−0.0022 (8)	−0.0002 (8)	−0.0039 (9)
C5A	0.0553 (13)	0.0746 (16)	0.0290 (9)	0.0188 (12)	0.0049 (9)	−0.0010 (10)
C6A	0.0249 (9)	0.0415 (11)	0.0668 (13)	0.0009 (8)	0.0063 (8)	0.0188 (10)
C2A	0.039 (3)	0.0357 (19)	0.046 (2)	0.0162 (19)	0.0037 (15)	0.0059 (16)
N4A	0.042 (2)	0.0491 (19)	0.037 (2)	0.0142 (18)	0.0043 (13)	0.0055 (14)
N4B	0.008 (3)	0.029 (3)	0.020 (3)	−0.007 (2)	0.0021 (16)	−0.0089 (19)
C2B	0.007 (3)	0.017 (2)	0.016 (3)	−0.003 (2)	0.0009 (16)	−0.0031 (19)

Geometric parameters (Å, º)

N1—C5	1.368 (2)	C3A—N4B	1.490 (6)
N1—C2	1.388 (2)	C3A—C2A	1.525 (5)
N1—H1	0.94 (3)	C3A—H3AA	0.9800
C2—O21	1.206 (2)	C3A—H3AB	0.9800
C2—N3	1.380 (2)	C3A—H3AC	0.9800
N3—N6	1.3629 (19)	C3A—H3AD	0.9801
N3—C4	1.454 (2)	C3A—H3AE	0.9800
C4—C5	1.513 (2)	C3A—H3AF	0.9800
C4—H4A	0.9900	C5A—N4A	1.479 (4)
C4—H4B	0.9900	C5A—N4B	1.527 (5)
C5—O51	1.209 (2)	C5A—H5AA	0.9800
N6—C7	1.289 (2)	C5A—H5AB	0.9800
C7—C8	1.441 (2)	C5A—H5AC	0.9800
C7—H7	0.9500	C5A—H5AD	0.9800
C8—C12	1.366 (2)	C5A—H5AE	0.9800
C8—O9	1.372 (2)	C5A—H5AF	0.9800
O9—C10	1.354 (2)	C6A—C2B	1.501 (6)
C10—C11	1.348 (2)	C6A—N4A	1.539 (5)
C10—N13	1.423 (2)	C6A—H6AA	0.9800
C11—C12	1.414 (2)	C6A—H6AB	0.9800
C11—H11	0.9500	C6A—H6AC	0.9800
C12—H12	0.9500	C6A—H6AD	0.9800
N13—O14	1.228 (2)	C6A—H6AE	0.9800
N13—O15	1.233 (2)	C6A—H6AF	0.9800
O1A—C2B	1.274 (5)	C2A—N4A	1.286 (6)
O1A—C2A	1.303 (5)	N4B—C2B	1.402 (8)
C5—N1—C2	112.89 (14)	H3AE—C3A—H3AF	109.5
C5—N1—H1	124.2 (16)	N4A—C5A—H5AA	109.5
C2—N1—H1	122.5 (16)	N4B—C5A—H5AA	133.3
O21—C2—N3	127.34 (15)	N4A—C5A—H5AB	109.5
O21—C2—N1	126.86 (15)	N4B—C5A—H5AB	76.6
N3—C2—N1	105.80 (14)	H5AA—C5A—H5AB	109.5
N6—N3—C2	119.38 (14)	N4A—C5A—H5AC	109.5
N6—N3—C4	127.91 (13)	N4B—C5A—H5AC	111.6
C2—N3—C4	112.66 (13)	H5AA—C5A—H5AC	109.5
N3—C4—C5	101.48 (13)	H5AB—C5A—H5AC	109.5
N3—C4—H4A	111.5	N4A—C5A—H5AD	144.1
C5—C4—H4A	111.5	N4B—C5A—H5AD	109.3
N3—C4—H4B	111.5	H5AA—C5A—H5AD	98.2
C5—C4—H4B	111.5	H5AC—C5A—H5AD	80.9
H4A—C4—H4B	109.3	N4A—C5A—H5AE	89.9
O51—C5—N1	126.24 (16)	N4B—C5A—H5AE	109.6
O51—C5—C4	126.69 (16)	H5AB—C5A—H5AE	105.3
N1—C5—C4	107.07 (14)	H5AC—C5A—H5AE	130.8
C7—N6—N3	116.08 (14)	H5AD—C5A—H5AE	109.5
N6—C7—C8	119.65 (15)	N4A—C5A—H5AF	90.8
N6—C7—H7	120.2	N4B—C5A—H5AF	109.6
C8—C7—H7	120.2	H5AA—C5A—H5AF	95.1
C12—C8—O9	110.49 (14)	H5AB—C5A—H5AF	139.6
C12—C8—C7	131.27 (16)	H5AD—C5A—H5AF	109.5
O9—C8—C7	118.23 (14)	H5AE—C5A—H5AF	109.5
C10—O9—C8	104.75 (12)	C2B—C6A—H6AA	115.6
C11—C10—O9	112.89 (15)	N4A—C6A—H6AA	109.5
C11—C10—N13	131.86 (16)	C2B—C6A—H6AB	131.6
O9—C10—N13	115.17 (14)	N4A—C6A—H6AB	109.5
C10—C11—C12	105.25 (14)	H6AA—C6A—H6AB	109.5
C10—C11—H11	127.4	C2B—C6A—H6AC	71.5
C12—C11—H11	127.4	N4A—C6A—H6AC	109.5
C8—C12—C11	106.62 (15)	H6AA—C6A—H6AC	109.5
C8—C12—H12	126.7	H6AB—C6A—H6AC	109.5
C11—C12—H12	126.7	C2B—C6A—H6AD	109.6
O14—N13—O15	124.76 (16)	N4A—C6A—H6AD	70.7
O14—N13—C10	118.68 (15)	H6AA—C6A—H6AD	80.7
O15—N13—C10	116.54 (15)	H6AB—C6A—H6AD	60.9
N4B—C3A—H3AA	84.6	H6AC—C6A—H6AD	168.5
C2A—C3A—H3AA	109.5	C2B—C6A—H6AE	109.5
N4B—C3A—H3AB	144.7	N4A—C6A—H6AE	124.3
C2A—C3A—H3AB	109.5	H6AB—C6A—H6AE	118.5
H3AA—C3A—H3AB	109.5	H6AC—C6A—H6AE	80.2
N4B—C3A—H3AC	94.8	H6AD—C6A—H6AE	109.5
C2A—C3A—H3AC	109.5	C2B—C6A—H6AF	109.4
H3AA—C3A—H3AC	109.5	N4A—C6A—H6AF	123.2
H3AB—C3A—H3AC	109.5	H6AA—C6A—H6AF	127.0
N4B—C3A—H3AD	109.2	H6AB—C6A—H6AF	49.1
C2A—C3A—H3AD	145.3	H6AC—C6A—H6AF	60.4
H3AA—C3A—H3AD	49.3	H6AD—C6A—H6AF	109.5
H3AB—C3A—H3AD	104.1	H6AE—C6A—H6AF	109.5
H3AC—C3A—H3AD	65.5	N4A—C2A—O1A	117.8 (5)
N4B—C3A—H3AE	109.6	N4A—C2A—C3A	114.0 (4)
C2A—C3A—H3AE	90.8	O1A—C2A—C3A	128.1 (3)
H3AA—C3A—H3AE	158.4	C2A—N4A—C5A	122.1 (5)
H3AB—C3A—H3AE	68.5	C2A—N4A—C6A	115.9 (4)
H3AC—C3A—H3AE	54.7	C5A—N4A—C6A	122.0 (3)
H3AD—C3A—H3AE	109.5	C2B—N4B—C3A	116.6 (5)
N4B—C3A—H3AF	109.7	C2B—N4B—C5A	115.8 (5)
C2A—C3A—H3AF	88.4	C3A—N4B—C5A	126.9 (4)
H3AA—C3A—H3AF	79.2	O1A—C2B—N4B	111.6 (5)
H3AB—C3A—H3AF	46.3	O1A—C2B—C6A	136.1 (4)
H3AC—C3A—H3AF	154.9	N4B—C2B—C6A	112.3 (4)
H3AD—C3A—H3AF	109.5
C5—N1—C2—O21	−178.06 (16)	O9—C10—N13—O14	−6.2 (2)
C5—N1—C2—N3	1.33 (18)	C11—C10—N13—O15	−8.1 (3)
O21—C2—N3—N6	−2.1 (3)	O9—C10—N13—O15	175.38 (14)
N1—C2—N3—N6	178.48 (13)	C2B—O1A—C2A—N4A	0.8 (3)
O21—C2—N3—C4	−179.67 (16)	C2B—O1A—C2A—C3A	176.8 (4)
N1—C2—N3—C4	0.94 (18)	N4B—C3A—C2A—N4A	−5.0 (3)
N6—N3—C4—C5	−179.80 (14)	N4B—C3A—C2A—O1A	178.9 (5)
C2—N3—C4—C5	−2.53 (17)	O1A—C2A—N4A—C5A	178.5 (2)
C2—N1—C5—O51	176.88 (16)	C3A—C2A—N4A—C5A	2.0 (4)
C2—N1—C5—C4	−2.93 (18)	O1A—C2A—N4A—C6A	−1.6 (3)
N3—C4—C5—O51	−176.64 (16)	C3A—C2A—N4A—C6A	−178.12 (19)
N3—C4—C5—N1	3.17 (16)	N4B—C5A—N4A—C2A	3.5 (3)
C2—N3—N6—C7	−172.06 (14)	N4B—C5A—N4A—C6A	−176.4 (4)
C4—N3—N6—C7	5.1 (2)	C2B—C6A—N4A—C2A	0.5 (3)
N3—N6—C7—C8	179.04 (14)	C2B—C6A—N4A—C5A	−179.6 (4)
N6—C7—C8—C12	−173.89 (17)	C2A—C3A—N4B—C2B	2.5 (3)
N6—C7—C8—O9	5.3 (2)	C2A—C3A—N4B—C5A	172.3 (5)
C12—C8—O9—C10	−0.68 (17)	N4A—C5A—N4B—C2B	−0.8 (3)
C7—C8—O9—C10	179.98 (14)	N4A—C5A—N4B—C3A	−170.7 (6)
C8—O9—C10—C11	0.64 (18)	C2A—O1A—C2B—N4B	1.4 (3)
C8—O9—C10—N13	177.83 (13)	C2A—O1A—C2B—C6A	179.7 (6)
O9—C10—C11—C12	−0.4 (2)	C3A—N4B—C2B—O1A	−5.5 (5)
N13—C10—C11—C12	−176.93 (17)	C5A—N4B—C2B—O1A	−176.4 (3)
O9—C8—C12—C11	0.49 (19)	C3A—N4B—C2B—C6A	175.8 (3)
C7—C8—C12—C11	179.71 (17)	C5A—N4B—C2B—C6A	4.8 (4)
C10—C11—C12—C8	−0.09 (19)	N4A—C6A—C2B—O1A	179.2 (6)
C11—C10—N13—O14	170.30 (18)	N4A—C6A—C2B—N4B	−2.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1A	0.94 (3)	1.82 (3)	2.7533 (19)	169 (2)
C7—H7···O21^i	0.95	2.34	3.123 (2)	139

Symmetry code: (i) x+1, y, z.

(Id) (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dion dimethylacetamide monosolvate

Crystal data

C8H6N4O5·C4H9NO	F(000) = 680
Mr = 325.29	Dx = 1.474 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.2038 (16) Å	Cell parameters from 5010 reflections
b = 7.4215 (5) Å	θ = 3.3–25.7°
c = 13.1195 (12) Å	µ = 0.12 mm^−1
β = 111.681 (7)°	T = 173 K
V = 1466.1 (2) Å^3	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer	1584 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.147
Graphite monochromator	θmax = 25.6°, θmin = 3.2°
ω scans	h = −19→19
17332 measured reflections	k = −9→9
2743 independent reflections	l = −14→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ^2(Fo^2) + (0.0409P)^2] where P = (Fo^2 + 2Fc^2)/3
2743 reflections	(Δ/σ)max < 0.001
231 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.44048 (14)	0.8147 (3)	0.47492 (17)	0.0265 (5)
H1	0.4047 (18)	0.864 (4)	0.501 (2)	0.035 (8)*
C2	0.51946 (15)	0.7335 (3)	0.5398 (2)	0.0262 (6)
O21	0.54928 (12)	0.7235 (3)	0.63849 (14)	0.0374 (5)
N3	0.55619 (13)	0.6646 (3)	0.46797 (16)	0.0255 (5)
C4	0.50279 (16)	0.7062 (4)	0.35406 (19)	0.0292 (6)
H4A	0.4834	0.5953	0.3097	0.035*
H4B	0.5356	0.7840	0.3207	0.035*
C5	0.42524 (16)	0.8044 (3)	0.3653 (2)	0.0287 (6)
O51	0.36091 (12)	0.8639 (3)	0.29181 (15)	0.0413 (5)
N6	0.63847 (13)	0.5897 (3)	0.50853 (16)	0.0260 (5)
C7	0.67150 (15)	0.5385 (3)	0.4376 (2)	0.0273 (6)
H7	0.6379	0.5509	0.3614	0.033*
C8	0.75898 (16)	0.4629 (3)	0.4740 (2)	0.0280 (6)
O9	0.80569 (11)	0.4382 (2)	0.58451 (14)	0.0317 (4)
C10	0.88552 (16)	0.3719 (4)	0.5922 (2)	0.0333 (6)
C11	0.89241 (17)	0.3522 (4)	0.4937 (2)	0.0366 (7)
H11	0.9422	0.3088	0.4792	0.044*
C12	0.81008 (17)	0.4095 (4)	0.4164 (2)	0.0341 (6)
H12	0.7932	0.4109	0.3390	0.041*
N13	0.94479 (16)	0.3229 (4)	0.6983 (2)	0.0453 (6)
O14	0.92013 (14)	0.3342 (3)	0.77664 (17)	0.0559 (6)
O15	1.01833 (14)	0.2656 (4)	0.70567 (19)	0.0713 (8)
O1A	0.34129 (11)	0.9862 (3)	0.57493 (17)	0.0418 (5)
C3A	0.21805 (19)	1.0507 (4)	0.3933 (2)	0.0410 (7)
H3A1	0.1565	1.0918	0.3724	0.062*	0.532 (12)
H3A2	0.2189	0.9327	0.3602	0.062*	0.532 (12)
H3A3	0.2514	1.1376	0.3673	0.062*	0.532 (12)
H3A4	0.1996	1.1625	0.3512	0.062*	0.468 (12)
H3A5	0.1841	0.9494	0.3499	0.062*	0.468 (12)
H3A6	0.2816	1.0308	0.4105	0.062*	0.468 (12)
C6A	0.25463 (19)	1.0653 (4)	0.6961 (2)	0.0421 (7)
H6A1	0.2124	1.0995	0.7303	0.063*	0.532 (12)
H6A2	0.3059	1.1466	0.7214	0.063*	0.532 (12)
H6A3	0.2746	0.9412	0.7166	0.063*	0.532 (12)
H6A4	0.3115	1.0672	0.7585	0.063*	0.468 (12)
H6A5	0.2177	0.9671	0.7057	0.063*	0.468 (12)
H6A6	0.2240	1.1804	0.6922	0.063*	0.468 (12)
C5A	0.11593 (18)	1.1268 (5)	0.5101 (3)	0.0602 (10)
H5A1	0.0858	1.1556	0.5605	0.090*	0.532 (12)
H5A2	0.0860	1.0248	0.4636	0.090*	0.532 (12)
H5A3	0.1140	1.2317	0.4639	0.090*	0.532 (12)
H5A4	0.0692	1.1437	0.4376	0.090*	0.468 (12)
H5A5	0.1268	1.2409	0.5505	0.090*	0.468 (12)
H5A6	0.0970	1.0353	0.5508	0.090*	0.468 (12)
N4A	0.2105 (4)	1.0782 (6)	0.5745 (6)	0.0275 (18)	0.532 (12)
C2A	0.2596 (6)	1.0357 (7)	0.5153 (7)	0.0293 (19)	0.532 (12)
N4B	0.2018 (5)	1.0649 (7)	0.4979 (7)	0.034 (2)	0.468 (12)
C2B	0.2713 (5)	1.0359 (8)	0.5899 (8)	0.030 (2)	0.468 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0268 (11)	0.0306 (13)	0.0243 (11)	0.0023 (9)	0.0120 (9)	−0.0002 (9)
C2	0.0239 (12)	0.0277 (14)	0.0279 (15)	−0.0018 (11)	0.0107 (11)	−0.0001 (11)
O21	0.0396 (10)	0.0545 (13)	0.0184 (10)	0.0106 (9)	0.0111 (8)	0.0023 (8)
N3	0.0237 (10)	0.0360 (13)	0.0186 (10)	0.0003 (9)	0.0101 (8)	0.0004 (9)
C4	0.0295 (13)	0.0375 (16)	0.0196 (13)	−0.0018 (11)	0.0077 (10)	0.0010 (11)
C5	0.0291 (13)	0.0305 (15)	0.0256 (14)	−0.0058 (11)	0.0091 (11)	0.0010 (11)
O51	0.0356 (10)	0.0533 (13)	0.0307 (10)	0.0089 (9)	0.0072 (9)	0.0093 (9)
N6	0.0255 (10)	0.0282 (12)	0.0260 (11)	−0.0041 (9)	0.0113 (9)	−0.0008 (9)
C7	0.0257 (13)	0.0320 (15)	0.0244 (13)	−0.0028 (11)	0.0094 (11)	−0.0038 (11)
C8	0.0301 (13)	0.0297 (14)	0.0229 (13)	−0.0045 (11)	0.0084 (11)	−0.0058 (11)
O9	0.0298 (9)	0.0372 (11)	0.0269 (10)	0.0017 (8)	0.0091 (8)	−0.0020 (8)
C10	0.0261 (13)	0.0370 (16)	0.0323 (15)	0.0025 (12)	0.0055 (11)	−0.0051 (12)
C11	0.0292 (14)	0.0411 (17)	0.0400 (16)	0.0030 (12)	0.0133 (12)	−0.0073 (13)
C12	0.0332 (14)	0.0410 (17)	0.0306 (14)	−0.0010 (12)	0.0148 (12)	−0.0076 (12)
N13	0.0363 (13)	0.0508 (17)	0.0398 (15)	0.0101 (12)	0.0035 (11)	−0.0033 (12)
O14	0.0532 (13)	0.0788 (17)	0.0322 (12)	0.0126 (12)	0.0118 (10)	0.0052 (11)
O15	0.0419 (13)	0.111 (2)	0.0498 (14)	0.0319 (14)	0.0039 (10)	−0.0039 (14)
O1A	0.0283 (10)	0.0415 (12)	0.0583 (13)	0.0043 (9)	0.0191 (10)	−0.0049 (10)
C3A	0.0450 (16)	0.0526 (19)	0.0250 (14)	−0.0009 (14)	0.0122 (13)	−0.0026 (13)
C6A	0.0403 (16)	0.059 (2)	0.0283 (15)	0.0010 (14)	0.0144 (13)	−0.0047 (13)
C5A	0.0235 (14)	0.053 (2)	0.101 (3)	0.0102 (14)	0.0183 (16)	0.010 (2)
N4A	0.023 (3)	0.033 (3)	0.026 (4)	0.000 (2)	0.010 (2)	0.0008 (19)
C2A	0.034 (5)	0.030 (3)	0.026 (4)	−0.009 (3)	0.014 (3)	−0.009 (2)
N4B	0.025 (4)	0.039 (3)	0.036 (5)	0.000 (2)	0.010 (3)	0.000 (3)
C2B	0.027 (5)	0.029 (3)	0.035 (5)	−0.007 (3)	0.013 (4)	−0.007 (3)

Geometric parameters (Å, º)

N1—C5	1.369 (3)	C3A—N4B	1.493 (9)
N1—C2	1.386 (3)	C3A—C2A	1.493 (9)
N1—H1	0.86 (3)	C3A—H3A1	0.9800
C2—O21	1.206 (3)	C3A—H3A2	0.9800
C2—N3	1.385 (3)	C3A—H3A3	0.9800
N3—N6	1.358 (3)	C3A—H3A4	0.9799
N3—C4	1.457 (3)	C3A—H3A5	0.9800
C4—C5	1.506 (4)	C3A—H3A6	0.9801
C4—H4A	0.9900	C6A—N4A	1.492 (7)
C4—H4B	0.9900	C6A—C2B	1.529 (10)
C5—O51	1.212 (3)	C6A—H6A1	0.9800
N6—C7	1.291 (3)	C6A—H6A2	0.9800
C7—C8	1.432 (3)	C6A—H6A3	0.9800
C7—H7	0.9500	C6A—H6A4	0.9800
C8—C12	1.370 (4)	C6A—H6A5	0.9799
C8—O9	1.377 (3)	C6A—H6A6	0.9800
O9—C10	1.352 (3)	C5A—N4A	1.495 (7)
C10—C11	1.346 (4)	C5A—N4B	1.529 (9)
C10—N13	1.416 (3)	C5A—H5A1	0.9800
C11—C12	1.410 (4)	C5A—H5A2	0.9800
C11—H11	0.9500	C5A—H5A3	0.9800
C12—H12	0.9500	C5A—H5A4	0.9799
N13—O15	1.235 (3)	C5A—H5A5	0.9799
N13—O14	1.236 (3)	C5A—H5A6	0.9800
O1A—C2B	1.276 (9)	N4A—C2A	1.340 (13)
O1A—C2A	1.317 (9)	N4B—C2B	1.329 (15)
C5—N1—C2	112.8 (2)	N4A—C6A—H6A2	109.5
C5—N1—H1	124.2 (18)	C2B—C6A—H6A2	89.0
C2—N1—H1	122.9 (18)	H6A1—C6A—H6A2	109.5
O21—C2—N3	127.3 (2)	N4A—C6A—H6A3	109.5
O21—C2—N1	126.8 (2)	C2B—C6A—H6A3	88.0
N3—C2—N1	105.9 (2)	H6A1—C6A—H6A3	109.5
N6—N3—C2	119.40 (19)	H6A2—C6A—H6A3	109.5
N6—N3—C4	127.9 (2)	N4A—C6A—H6A4	145.4
C2—N3—C4	112.2 (2)	C2B—C6A—H6A4	109.5
N3—C4—C5	101.73 (19)	H6A1—C6A—H6A4	102.3
N3—C4—H4A	111.4	H6A3—C6A—H6A4	70.8
C5—C4—H4A	111.4	N4A—C6A—H6A5	96.4
N3—C4—H4B	111.4	C2B—C6A—H6A5	109.4
C5—C4—H4B	111.4	H6A1—C6A—H6A5	64.6
H4A—C4—H4B	109.3	H6A2—C6A—H6A5	153.6
O51—C5—N1	125.7 (2)	H6A3—C6A—H6A5	54.6
O51—C5—C4	127.0 (2)	H6A4—C6A—H6A5	109.5
N1—C5—C4	107.3 (2)	N4A—C6A—H6A6	81.6
C7—N6—N3	116.5 (2)	C2B—C6A—H6A6	109.4
N6—C7—C8	119.8 (2)	H6A1—C6A—H6A6	51.1
N6—C7—H7	120.1	H6A2—C6A—H6A6	80.3
C8—C7—H7	120.1	H6A3—C6A—H6A6	160.5
C12—C8—O9	109.5 (2)	H6A4—C6A—H6A6	109.5
C12—C8—C7	130.9 (2)	H6A5—C6A—H6A6	109.5
O9—C8—C7	119.7 (2)	N4A—C5A—H5A1	109.5
C10—O9—C8	105.40 (19)	N4B—C5A—H5A1	146.7
C11—C10—O9	112.6 (2)	N4A—C5A—H5A2	109.5
C11—C10—N13	130.5 (2)	N4B—C5A—H5A2	87.9
O9—C10—N13	116.7 (2)	H5A1—C5A—H5A2	109.5
C10—C11—C12	105.4 (2)	N4A—C5A—H5A3	109.5
C10—C11—H11	127.3	N4B—C5A—H5A3	89.8
C12—C11—H11	127.3	H5A1—C5A—H5A3	109.5
C8—C12—C11	107.2 (2)	H5A2—C5A—H5A3	109.5
C8—C12—H12	126.4	N4A—C5A—H5A4	147.3
C11—C12—H12	126.4	N4B—C5A—H5A4	110.1
O15—N13—O14	123.9 (2)	H5A1—C5A—H5A4	103.2
O15—N13—C10	116.8 (3)	H5A2—C5A—H5A4	57.9
O14—N13—C10	119.3 (2)	H5A3—C5A—H5A4	57.4
N4B—C3A—H3A1	74.3	N4A—C5A—H5A5	87.8
C2A—C3A—H3A1	109.5	N4B—C5A—H5A5	109.1
N4B—C3A—H3A2	120.4	H5A1—C5A—H5A5	58.7
C2A—C3A—H3A2	109.5	H5A2—C5A—H5A5	162.2
H3A1—C3A—H3A2	109.5	H5A3—C5A—H5A5	66.8
N4B—C3A—H3A3	125.5	H5A4—C5A—H5A5	109.5
C2A—C3A—H3A3	109.5	N4A—C5A—H5A6	89.2
H3A1—C3A—H3A3	109.5	N4B—C5A—H5A6	109.2
H3A2—C3A—H3A3	109.5	H5A1—C5A—H5A6	56.6
N4B—C3A—H3A4	109.7	H5A2—C5A—H5A6	67.8
C2A—C3A—H3A4	126.2	H5A3—C5A—H5A6	160.4
H3A1—C3A—H3A4	60.8	H5A4—C5A—H5A6	109.5
H3A2—C3A—H3A4	123.9	H5A5—C5A—H5A6	109.5
H3A3—C3A—H3A4	48.7	C2A—N4A—C6A	116.9 (7)
N4B—C3A—H3A5	109.7	C2A—N4A—C5A	115.7 (8)
C2A—C3A—H3A5	119.9	C6A—N4A—C5A	127.3 (5)
H3A1—C3A—H3A5	77.4	O1A—C2A—N4A	113.8 (8)
H3A3—C3A—H3A5	124.5	O1A—C2A—C3A	127.9 (6)
H3A4—C3A—H3A5	109.5	N4A—C2A—C3A	118.3 (8)
N4B—C3A—H3A6	109.0	O1A—C2A—H3A6	90.7
C2A—C3A—H3A6	73.9	N4A—C2A—H3A6	154.8
H3A1—C3A—H3A6	170.0	C2B—N4B—C3A	116.5 (9)
H3A2—C3A—H3A6	77.3	C2B—N4B—C5A	116.8 (9)
H3A3—C3A—H3A6	60.8	C3A—N4B—C5A	126.4 (6)
H3A4—C3A—H3A6	109.5	O1A—C2B—N4B	114.2 (10)
H3A5—C3A—H3A6	109.5	O1A—C2B—C6A	130.4 (7)
N4A—C6A—H6A1	109.5	N4B—C2B—C6A	115.4 (8)
C2B—C6A—H6A1	147.3
C5—N1—C2—O21	179.7 (3)	O9—C10—N13—O15	−178.7 (3)
C5—N1—C2—N3	−1.1 (3)	C11—C10—N13—O14	−171.2 (3)
O21—C2—N3—N6	−6.4 (4)	O9—C10—N13—O14	3.4 (4)
N1—C2—N3—N6	174.4 (2)	C2B—C6A—N4A—C2A	−1.1 (5)
O21—C2—N3—C4	−178.6 (3)	C2B—C6A—N4A—C5A	176.4 (7)
N1—C2—N3—C4	2.3 (3)	N4B—C5A—N4A—C2A	2.0 (4)
N6—N3—C4—C5	−173.8 (2)	N4B—C5A—N4A—C6A	−175.5 (7)
C2—N3—C4—C5	−2.4 (3)	C2B—O1A—C2A—N4A	0.7 (4)
C2—N1—C5—O51	179.6 (3)	C2B—O1A—C2A—C3A	−180.0 (8)
C2—N1—C5—C4	−0.4 (3)	C6A—N4A—C2A—O1A	0.6 (6)
N3—C4—C5—O51	−178.4 (3)	C5A—N4A—C2A—O1A	−177.2 (4)
N3—C4—C5—N1	1.6 (3)	C6A—N4A—C2A—C3A	−178.8 (4)
C2—N3—N6—C7	−175.6 (2)	C5A—N4A—C2A—C3A	3.4 (6)
C4—N3—N6—C7	−4.8 (3)	N4B—C3A—C2A—O1A	176.0 (8)
N3—N6—C7—C8	178.3 (2)	N4B—C3A—C2A—N4A	−4.8 (4)
N6—C7—C8—C12	−175.5 (3)	C2A—C3A—N4B—C2B	0.8 (5)
N6—C7—C8—O9	2.8 (4)	C2A—C3A—N4B—C5A	174.5 (8)
C12—C8—O9—C10	0.8 (3)	N4A—C5A—N4B—C2B	1.6 (4)
C7—C8—O9—C10	−177.9 (2)	N4A—C5A—N4B—C3A	−172.2 (7)
C8—O9—C10—C11	−0.3 (3)	C2A—O1A—C2B—N4B	2.9 (4)
C8—O9—C10—N13	−175.9 (2)	C2A—O1A—C2B—C6A	−177.8 (9)
O9—C10—C11—C12	−0.3 (3)	C3A—N4B—C2B—O1A	−5.0 (7)
N13—C10—C11—C12	174.5 (3)	C5A—N4B—C2B—O1A	−179.4 (4)
O9—C8—C12—C11	−1.0 (3)	C3A—N4B—C2B—C6A	175.5 (4)
C7—C8—C12—C11	177.5 (3)	C5A—N4B—C2B—C6A	1.2 (7)
C10—C11—C12—C8	0.8 (3)	N4A—C6A—C2B—O1A	178.2 (9)
C11—C10—N13—O15	6.7 (5)	N4A—C6A—C2B—N4B	−2.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1A	0.86 (3)	1.88 (3)	2.736 (3)	172 (3)
C7—H7···O51^i	0.95	2.45	3.137 (3)	129

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(Ie) (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione dimethylacetamide disolvat

Crystal data

C8H6N4O5·2C4H9NO	F(000) = 872
Mr = 412.41	Dx = 1.327 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.874 (2) Å	Cell parameters from 8474 reflections
b = 11.5433 (9) Å	θ = 3.5–25.9°
c = 8.7162 (9) Å	µ = 0.11 mm^−1
β = 100.708 (9)°	T = 173 K
V = 2063.6 (3) Å^3	Block, yellow
Z = 4	0.60 × 0.60 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer	2943 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.078
Graphite monochromator	θmax = 25.6°, θmin = 3.5°
ω scans	h = −25→23
9751 measured reflections	k = −13→13
3844 independent reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0809P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
3844 reflections	Δρmax = 0.26 e Å^−3
285 parameters	Δρmin = −0.24 e Å^−3
22 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.027 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.66679 (7)	0.53815 (13)	0.41046 (17)	0.0360 (3)
H1	0.6368 (14)	0.492 (2)	0.341 (3)	0.073 (8)*
C2	0.70735 (8)	0.48757 (15)	0.53845 (19)	0.0348 (4)
O21	0.70772 (7)	0.38678 (11)	0.57660 (16)	0.0484 (4)
N3	0.74634 (7)	0.57599 (11)	0.60893 (15)	0.0328 (3)
C4	0.73370 (8)	0.68598 (14)	0.52766 (18)	0.0327 (4)
H4A	0.7727	0.7145	0.4898	0.039*
H4B	0.7190	0.7457	0.5950	0.039*
C5	0.67955 (8)	0.65254 (15)	0.39306 (18)	0.0332 (4)
O51	0.65300 (6)	0.71682 (11)	0.29060 (14)	0.0440 (3)
N6	0.79325 (7)	0.55227 (12)	0.73625 (15)	0.0317 (3)
C7	0.82855 (8)	0.63851 (14)	0.79451 (18)	0.0310 (4)
H7	0.8210	0.7135	0.7499	0.037*
C8	0.87985 (8)	0.62031 (14)	0.92860 (18)	0.0311 (4)
O9	0.89185 (5)	0.50962 (9)	0.98338 (12)	0.0305 (3)
C10	0.94202 (8)	0.52129 (15)	1.10720 (19)	0.0326 (4)
C11	0.96170 (8)	0.63200 (16)	1.1323 (2)	0.0385 (4)
H11	0.9956	0.6603	1.2114	0.046*
C12	0.92099 (8)	0.69690 (15)	1.0155 (2)	0.0375 (4)
H12	0.9221	0.7783	1.0005	0.045*
N13	0.96523 (7)	0.41673 (13)	1.18270 (18)	0.0386 (4)
O14	0.93963 (6)	0.32441 (11)	1.13676 (16)	0.0482 (4)
O15	1.01178 (7)	0.42607 (13)	1.29381 (17)	0.0539 (4)
C3A	0.74350 (11)	1.0515 (2)	0.6033 (2)	0.0528 (5)
H3A1	0.7645	1.0803	0.5192	0.079*	0.926 (5)
H3A2	0.7168	1.1131	0.6365	0.079*	0.926 (5)
H3A3	0.7158	0.9851	0.5656	0.079*	0.926 (5)
H3A4	0.7192	1.1159	0.5466	0.079*	0.074 (5)
H3A5	0.7129	0.9973	0.6378	0.079*	0.074 (5)
H3A6	0.7683	1.0112	0.5345	0.079*	0.074 (5)
O1A	0.80822 (7)	0.91085 (10)	0.76794 (17)	0.0494 (4)
C5A	0.81159 (12)	1.22201 (16)	0.8097 (3)	0.0574 (6)
H5A1	0.7971	1.2384	0.6983	0.086*	0.926 (5)
H5A2	0.8508	1.2674	0.8497	0.086*	0.926 (5)
H5A3	0.7770	1.2429	0.8666	0.086*	0.926 (5)
H5A4	0.7847	1.2800	0.7453	0.086*	0.074 (5)
H5A5	0.8576	1.2349	0.8048	0.086*	0.074 (5)
H5A6	0.8055	1.2288	0.9181	0.086*	0.074 (5)
C6A	0.87552 (10)	1.06610 (17)	0.9677 (2)	0.0477 (5)
H6A1	0.8616	1.0933	1.0629	0.072*	0.926 (5)
H6A2	0.9173	1.1019	0.9597	0.072*	0.926 (5)
H6A3	0.8804	0.9817	0.9719	0.072*	0.926 (5)
H6A4	0.8702	1.1505	0.9648	0.072*	0.074 (5)
H6A5	0.9200	1.0464	0.9561	0.072*	0.074 (5)
H6A6	0.8675	1.0364	1.0678	0.072*	0.074 (5)
C2A	0.79502 (9)	1.01455 (16)	0.7401 (2)	0.0368 (6)	0.926 (5)
N4A	0.82642 (8)	1.09815 (13)	0.8311 (2)	0.0395 (5)	0.926 (5)
C2A'	0.8266 (9)	1.0112 (13)	0.834 (2)	0.031 (7)*	0.074 (5)
N4A'	0.7910 (9)	1.0991 (13)	0.748 (2)	0.045 (7)*	0.074 (5)
C3B	0.60868 (11)	0.2194 (2)	0.3047 (3)	0.0591 (6)
H3B1	0.5842	0.1623	0.3539	0.089*	0.881 (6)
H3B2	0.6395	0.2601	0.3854	0.089*	0.881 (6)
H3B3	0.6327	0.1798	0.2335	0.089*	0.881 (6)
H3B4	0.6207	0.1380	0.3250	0.089*	0.119 (6)
H3B5	0.6038	0.2572	0.4026	0.089*	0.119 (6)
H3B6	0.6428	0.2587	0.2610	0.089*	0.119 (6)
O1B	0.56823 (7)	0.41347 (12)	0.23160 (17)	0.0537 (4)
C5B	0.50137 (15)	0.1400 (2)	0.0829 (3)	0.0854 (9)
H5B1	0.4612	0.1273	0.0064	0.128*	0.881 (6)
H5B2	0.4983	0.1001	0.1804	0.128*	0.881 (6)
H5B3	0.5386	0.1096	0.0417	0.128*	0.881 (6)
H5B4	0.5154	0.0601	0.1072	0.128*	0.119 (6)
H5B5	0.5038	0.1572	−0.0260	0.128*	0.119 (6)
H5B6	0.4564	0.1497	0.0984	0.128*	0.119 (6)
C6B	0.46290 (12)	0.3472 (3)	0.0326 (3)	0.0775 (8)
H6B1	0.4283	0.3052	−0.0370	0.116*	0.881 (6)
H6B2	0.4844	0.4007	−0.0290	0.116*	0.881 (6)
H6B3	0.4439	0.3911	0.1093	0.116*	0.881 (6)
H6B4	0.4469	0.2693	0.0016	0.116*	0.119 (6)
H6B5	0.4714	0.3892	−0.0593	0.116*	0.119 (6)
H6B6	0.4299	0.3889	0.0777	0.116*	0.119 (6)
C2B	0.56159 (11)	0.3062 (2)	0.2134 (3)	0.0437 (7)	0.881 (6)
N4B	0.51037 (10)	0.26517 (18)	0.1130 (2)	0.0542 (7)	0.881 (6)
C2B'	0.5284 (8)	0.3380 (12)	0.1584 (19)	0.053 (6)*	0.119 (6)
N4B'	0.5474 (6)	0.2258 (11)	0.1942 (15)	0.047 (5)*	0.119 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0303 (7)	0.0406 (8)	0.0345 (7)	−0.0045 (6)	−0.0006 (6)	0.0006 (6)
C2	0.0314 (8)	0.0378 (9)	0.0344 (9)	−0.0036 (7)	0.0044 (7)	0.0023 (7)
O21	0.0476 (7)	0.0380 (7)	0.0542 (8)	−0.0106 (6)	−0.0047 (6)	0.0087 (6)
N3	0.0340 (7)	0.0325 (7)	0.0291 (7)	−0.0023 (6)	−0.0016 (6)	0.0034 (5)
C4	0.0354 (8)	0.0330 (9)	0.0284 (8)	−0.0002 (7)	0.0023 (6)	0.0005 (6)
C5	0.0298 (8)	0.0396 (9)	0.0300 (8)	0.0012 (7)	0.0054 (7)	−0.0004 (7)
O51	0.0423 (7)	0.0495 (8)	0.0361 (6)	0.0042 (6)	−0.0031 (5)	0.0074 (5)
N6	0.0305 (7)	0.0356 (7)	0.0278 (7)	0.0008 (6)	0.0023 (5)	0.0018 (5)
C7	0.0343 (8)	0.0299 (8)	0.0286 (8)	0.0026 (7)	0.0048 (6)	0.0003 (6)
C8	0.0309 (8)	0.0305 (8)	0.0316 (8)	0.0018 (7)	0.0049 (7)	−0.0010 (6)
O9	0.0263 (5)	0.0315 (6)	0.0317 (6)	0.0008 (4)	−0.0001 (5)	−0.0012 (4)
C10	0.0247 (7)	0.0392 (9)	0.0319 (8)	0.0023 (7)	0.0002 (6)	−0.0034 (7)
C11	0.0320 (8)	0.0429 (10)	0.0379 (9)	−0.0008 (7)	−0.0010 (7)	−0.0077 (7)
C12	0.0389 (9)	0.0310 (8)	0.0408 (9)	−0.0016 (7)	0.0031 (7)	−0.0037 (7)
N13	0.0293 (7)	0.0433 (8)	0.0413 (8)	0.0039 (6)	0.0018 (6)	0.0024 (6)
O14	0.0426 (7)	0.0368 (7)	0.0612 (8)	0.0011 (6)	−0.0005 (6)	0.0065 (6)
O15	0.0395 (7)	0.0634 (9)	0.0506 (8)	0.0074 (6)	−0.0133 (6)	0.0035 (6)
C3A	0.0483 (11)	0.0615 (13)	0.0474 (11)	0.0023 (10)	0.0057 (9)	0.0086 (9)
O1A	0.0585 (8)	0.0308 (7)	0.0609 (9)	−0.0011 (6)	0.0167 (7)	0.0028 (6)
C5A	0.0763 (14)	0.0305 (10)	0.0669 (13)	0.0080 (10)	0.0173 (11)	0.0036 (9)
C6A	0.0481 (10)	0.0477 (11)	0.0453 (10)	−0.0017 (9)	0.0033 (8)	0.0049 (8)
C2A	0.0383 (10)	0.0350 (11)	0.0401 (11)	−0.0002 (8)	0.0153 (9)	0.0040 (8)
N4A	0.0438 (10)	0.0314 (9)	0.0435 (10)	0.0044 (7)	0.0089 (8)	0.0048 (6)
C3B	0.0498 (11)	0.0551 (13)	0.0738 (14)	0.0010 (10)	0.0148 (10)	−0.0088 (11)
O1B	0.0461 (7)	0.0476 (8)	0.0609 (9)	−0.0120 (6)	−0.0068 (6)	−0.0081 (6)
C5B	0.102 (2)	0.0764 (17)	0.0851 (18)	−0.0538 (17)	0.0357 (16)	−0.0341 (14)
C6B	0.0633 (14)	0.0932 (18)	0.0636 (14)	−0.0358 (14)	−0.0201 (12)	0.0175 (13)
C2B	0.0424 (12)	0.0474 (15)	0.0434 (12)	−0.0128 (10)	0.0138 (10)	−0.0089 (9)
N4B	0.0576 (13)	0.0585 (13)	0.0454 (11)	−0.0291 (10)	0.0070 (9)	−0.0074 (9)

Geometric parameters (Å, º)

N1—C5	1.361 (2)	C5A—H5A5	0.9800
N1—C2	1.397 (2)	C5A—H5A6	0.9800
N1—H1	0.95 (3)	C6A—N4A	1.467 (2)
C2—O21	1.210 (2)	C6A—C2A'	1.538 (13)
C2—N3	1.377 (2)	C6A—H6A1	0.9800
N3—N6	1.3645 (18)	C6A—H6A2	0.9800
N3—C4	1.454 (2)	C6A—H6A3	0.9800
C4—C5	1.520 (2)	C6A—H6A4	0.9800
C4—H4A	0.9900	C6A—H6A5	0.9800
C4—H4B	0.9900	C6A—H6A6	0.9800
C5—O51	1.213 (2)	C2A—N4A	1.341 (3)
N6—C7	1.285 (2)	C2A'—N4A'	1.392 (17)
C7—C8	1.446 (2)	C3B—N4B'	1.452 (11)
C7—H7	0.9500	C3B—C2B	1.520 (3)
C8—C12	1.361 (2)	C3B—H3B1	0.9800
C8—O9	1.3707 (19)	C3B—H3B2	0.9800
O9—C10	1.3637 (18)	C3B—H3B3	0.9800
C10—C11	1.348 (2)	C3B—H3B4	0.9800
C10—N13	1.416 (2)	C3B—H3B5	0.9800
C11—C12	1.414 (2)	C3B—H3B6	0.9800
C11—H11	0.9500	O1B—C2B	1.253 (3)
C12—H12	0.9500	O1B—C2B'	1.289 (13)
N13—O14	1.2256 (19)	C5B—N4B	1.474 (3)
N13—O15	1.243 (2)	C5B—N4B'	1.581 (11)
C3A—C2A	1.511 (3)	C5B—H5B1	0.9800
C3A—N4A'	1.550 (14)	C5B—H5B2	0.9800
C3A—H3A1	0.9800	C5B—H5B3	0.9800
C3A—H3A2	0.9800	C5B—H5B4	0.9800
C3A—H3A3	0.9800	C5B—H5B5	0.9800
C3A—H3A4	0.9800	C5B—H5B6	0.9800
C3A—H3A5	0.9800	C6B—N4B	1.454 (3)
C3A—H3A6	0.9800	C6B—C2B'	1.589 (13)
O1A—C2A	1.242 (2)	C6B—H6B1	0.9800
O1A—C2A'	1.317 (13)	C6B—H6B2	0.9800
C5A—N4A	1.468 (2)	C6B—H6B3	0.9800
C5A—N4A'	1.551 (14)	C6B—H6B4	0.9800
C5A—H5A1	0.9800	C6B—H6B5	0.9800
C5A—H5A2	0.9800	C6B—H6B6	0.9800
C5A—H5A3	0.9800	C2B—N4B	1.336 (3)
C5A—H5A4	0.9800	C2B'—N4B'	1.374 (16)
C5—N1—C2	113.10 (14)	C2A'—C6A—H6A6	109.5
C5—N1—H1	126.6 (15)	H6A2—C6A—H6A6	120.8
C2—N1—H1	120.1 (15)	H6A3—C6A—H6A6	69.7
O21—C2—N3	128.12 (15)	H6A4—C6A—H6A6	109.5
O21—C2—N1	126.40 (15)	H6A5—C6A—H6A6	109.5
N3—C2—N1	105.47 (14)	O1A—C2A—N4A	120.77 (17)
N6—N3—C2	119.31 (13)	O1A—C2A—C3A	121.73 (18)
N6—N3—C4	127.54 (13)	N4A—C2A—C3A	117.50 (17)
C2—N3—C4	113.03 (13)	C2A—N4A—C6A	119.34 (15)
N3—C4—C5	101.29 (13)	C2A—N4A—C5A	123.88 (17)
N3—C4—H4A	111.5	C6A—N4A—C5A	116.64 (17)
C5—C4—H4A	111.5	O1A—C2A'—N4A'	108.9 (11)
N3—C4—H4B	111.5	O1A—C2A'—C6A	142.3 (12)
C5—C4—H4B	111.5	N4A'—C2A'—C6A	108.8 (10)
H4A—C4—H4B	109.3	C2A'—N4A'—C5A	113.1 (11)
O51—C5—N1	127.11 (15)	C2A'—N4A'—C3A	112.1 (10)
O51—C5—C4	125.83 (15)	C5A—N4A'—C3A	134.6 (11)
N1—C5—C4	107.06 (13)	N4B'—C3B—H3B1	81.9
C7—N6—N3	115.97 (13)	C2B—C3B—H3B1	109.5
N6—C7—C8	119.39 (14)	N4B'—C3B—H3B2	146.1
N6—C7—H7	120.3	C2B—C3B—H3B2	109.5
C8—C7—H7	120.3	H3B1—C3B—H3B2	109.5
C12—C8—O9	110.87 (13)	N4B'—C3B—H3B3	95.5
C12—C8—C7	130.66 (15)	C2B—C3B—H3B3	109.5
O9—C8—C7	118.48 (14)	H3B1—C3B—H3B3	109.5
C10—O9—C8	104.32 (12)	H3B2—C3B—H3B3	109.5
C11—C10—O9	112.84 (15)	N4B'—C3B—H3B4	109.5
C11—C10—N13	131.69 (15)	C2B—C3B—H3B4	147.7
O9—C10—N13	115.44 (14)	H3B1—C3B—H3B4	54.1
C10—C11—C12	105.16 (14)	H3B2—C3B—H3B4	102.6
C10—C11—H11	127.4	H3B3—C3B—H3B4	61.5
C12—C11—H11	127.4	N4B'—C3B—H3B5	109.5
C8—C12—C11	106.81 (15)	C2B—C3B—H3B5	90.0
C8—C12—H12	126.6	H3B1—C3B—H3B5	76.8
C11—C12—H12	126.6	H3B2—C3B—H3B5	47.3
O14—N13—O15	124.08 (15)	H3B3—C3B—H3B5	155.0
O14—N13—C10	119.90 (14)	H3B4—C3B—H3B5	109.5
O15—N13—C10	116.02 (15)	N4B'—C3B—H3B6	109.5
C2A—C3A—H3A1	109.5	C2B—C3B—H3B6	86.4
N4A'—C3A—H3A1	100.3	H3B1—C3B—H3B6	163.2
C2A—C3A—H3A2	109.5	H3B2—C3B—H3B6	68.3
N4A'—C3A—H3A2	79.5	H3B3—C3B—H3B6	58.3
H3A1—C3A—H3A2	109.5	H3B4—C3B—H3B6	109.5
C2A—C3A—H3A3	109.5	H3B5—C3B—H3B6	109.5
N4A'—C3A—H3A3	143.0	N4B—C5B—H5B1	109.5
H3A1—C3A—H3A3	109.5	N4B'—C5B—H5B1	149.0
H3A2—C3A—H3A3	109.5	N4B—C5B—H5B2	109.5
C2A—C3A—H3A4	146.9	N4B'—C5B—H5B2	83.8
N4A'—C3A—H3A4	109.5	H5B1—C5B—H5B2	109.5
H3A1—C3A—H3A4	68.1	N4B—C5B—H5B3	109.5
H3A2—C3A—H3A4	47.9	N4B'—C5B—H5B3	90.9
H3A3—C3A—H3A4	101.9	H5B1—C5B—H5B3	109.5
C2A—C3A—H3A5	89.2	H5B2—C5B—H5B3	109.5
N4A'—C3A—H3A5	109.5	N4B—C5B—H5B4	149.5
H3A1—C3A—H3A5	148.6	N4B'—C5B—H5B4	109.5
H3A2—C3A—H3A5	86.2	H5B1—C5B—H5B4	100.9
H3A4—C3A—H3A5	109.5	H5B2—C5B—H5B4	55.5
C2A—C3A—H3A6	88.2	H5B3—C5B—H5B4	61.0
N4A'—C3A—H3A6	109.5	N4B—C5B—H5B5	86.9
H3A1—C3A—H3A6	48.8	N4B'—C5B—H5B5	109.5
H3A2—C3A—H3A6	156.8	H5B1—C5B—H5B5	64.1
H3A3—C3A—H3A6	76.7	H5B2—C5B—H5B5	163.5
H3A4—C3A—H3A6	109.5	H5B3—C5B—H5B5	62.0
H3A5—C3A—H3A6	109.5	H5B4—C5B—H5B5	109.5
N4A—C5A—H5A1	109.5	N4B—C5B—H5B6	87.6
N4A'—C5A—H5A1	79.4	N4B'—C5B—H5B6	109.5
N4A—C5A—H5A2	109.5	H5B1—C5B—H5B6	52.4
N4A'—C5A—H5A2	140.6	H5B2—C5B—H5B6	73.4
H5A1—C5A—H5A2	109.5	H5B3—C5B—H5B6	159.6
N4A—C5A—H5A3	109.5	H5B4—C5B—H5B6	109.5
N4A'—C5A—H5A3	102.7	H5B5—C5B—H5B6	109.5
H5A1—C5A—H5A3	109.5	N4B—C6B—H6B1	109.5
H5A2—C5A—H5A3	109.5	C2B'—C6B—H6B1	146.5
N4A—C5A—H5A4	145.4	N4B—C6B—H6B2	109.5
N4A'—C5A—H5A4	109.5	C2B'—C6B—H6B2	89.8
H5A2—C5A—H5A4	100.9	H6B1—C6B—H6B2	109.5
H5A3—C5A—H5A4	74.0	N4B—C6B—H6B3	109.5
N4A—C5A—H5A5	88.1	C2B'—C6B—H6B3	88.2
N4A'—C5A—H5A5	109.5	H6B1—C6B—H6B3	109.5
H5A1—C5A—H5A5	93.0	H6B2—C6B—H6B3	109.5
H5A3—C5A—H5A5	143.6	N4B—C6B—H6B4	72.6
H5A4—C5A—H5A5	109.5	C2B'—C6B—H6B4	109.5
N4A—C5A—H5A6	91.0	H6B2—C6B—H6B4	126.5
N4A'—C5A—H5A6	109.5	H6B3—C6B—H6B4	120.2
H5A1—C5A—H5A6	150.2	N4B—C6B—H6B5	120.3
H5A2—C5A—H5A6	82.1	C2B'—C6B—H6B5	109.5
H5A4—C5A—H5A6	109.5	H6B1—C6B—H6B5	88.0
H5A5—C5A—H5A6	109.5	H6B3—C6B—H6B5	117.4
N4A—C6A—H6A1	109.5	H6B4—C6B—H6B5	109.5
C2A'—C6A—H6A1	121.1	N4B—C6B—H6B6	126.3
N4A—C6A—H6A2	109.5	C2B'—C6B—H6B6	109.5
C2A'—C6A—H6A2	126.4	H6B1—C6B—H6B6	90.0
H6A1—C6A—H6A2	109.5	H6B2—C6B—H6B6	109.8
N4A—C6A—H6A3	109.5	H6B4—C6B—H6B6	109.5
C2A'—C6A—H6A3	70.6	H6B5—C6B—H6B6	109.5
H6A1—C6A—H6A3	109.5	O1B—C2B—N4B	119.3 (2)
H6A2—C6A—H6A3	109.5	O1B—C2B—C3B	122.65 (19)
N4A—C6A—H6A4	70.7	N4B—C2B—C3B	118.0 (2)
C2A'—C6A—H6A4	109.5	C2B—N4B—C6B	118.4 (2)
H6A1—C6A—H6A4	69.7	C2B—N4B—C5B	121.6 (2)
H6A2—C6A—H6A4	71.2	C6B—N4B—C5B	120.0 (2)
H6A3—C6A—H6A4	179.1	O1B—C2B'—N4B'	113.1 (11)
N4A—C6A—H6A5	120.5	O1B—C2B'—C6B	133.6 (10)
C2A'—C6A—H6A5	109.5	N4B'—C2B'—C6B	113.3 (10)
H6A1—C6A—H6A5	126.7	C2B'—N4B'—C3B	112.4 (10)
H6A3—C6A—H6A5	71.2	C2B'—N4B'—C5B	109.5 (9)
H6A4—C6A—H6A5	109.5	C3B—N4B'—C5B	137.3 (9)
N4A—C6A—H6A6	127.0
C5—N1—C2—O21	−177.29 (18)	C2A'—C6A—N4A—C5A	174.0 (14)
C5—N1—C2—N3	2.2 (2)	N4A'—C5A—N4A—C2A	2.7 (15)
O21—C2—N3—N6	1.7 (3)	N4A'—C5A—N4A—C6A	−172.9 (15)
N1—C2—N3—N6	−177.80 (14)	C2A—O1A—C2A'—N4A'	2.6 (11)
O21—C2—N3—C4	178.06 (18)	C2A—O1A—C2A'—C6A	−174 (4)
N1—C2—N3—C4	−1.40 (19)	N4A—C6A—C2A'—O1A	173 (4)
N6—N3—C4—C5	176.26 (15)	N4A—C6A—C2A'—N4A'	−3.9 (10)
C2—N3—C4—C5	0.22 (18)	O1A—C2A'—N4A'—C5A	−176.8 (14)
C2—N1—C5—O51	178.19 (17)	C6A—C2A'—N4A'—C5A	1 (2)
C2—N1—C5—C4	−2.08 (19)	O1A—C2A'—N4A'—C3A	−1 (2)
N3—C4—C5—O51	−179.18 (16)	C6A—C2A'—N4A'—C3A	176.4 (13)
N3—C4—C5—N1	1.08 (17)	N4A—C5A—N4A'—C2A'	3.5 (11)
C2—N3—N6—C7	178.88 (15)	N4A—C5A—N4A'—C3A	−171 (3)
C4—N3—N6—C7	3.1 (2)	C2A—C3A—N4A'—C2A'	−1.5 (11)
N3—N6—C7—C8	−179.32 (14)	C2A—C3A—N4A'—C5A	173 (3)
N6—C7—C8—C12	−176.15 (18)	C2B'—O1B—C2B—N4B	3.7 (14)
N6—C7—C8—O9	4.1 (2)	C2B'—O1B—C2B—C3B	−174.5 (15)
C12—C8—O9—C10	−0.06 (18)	N4B'—C3B—C2B—O1B	174.0 (10)
C7—C8—O9—C10	179.77 (14)	N4B'—C3B—C2B—N4B	−4.3 (9)
C8—O9—C10—C11	0.01 (19)	O1B—C2B—N4B—C6B	−2.2 (3)
C8—O9—C10—N13	−178.21 (14)	C3B—C2B—N4B—C6B	176.2 (2)
O9—C10—C11—C12	0.0 (2)	O1B—C2B—N4B—C5B	177.8 (2)
N13—C10—C11—C12	177.89 (18)	C3B—C2B—N4B—C5B	−3.8 (3)
O9—C8—C12—C11	0.1 (2)	C2B'—C6B—N4B—C2B	−1.8 (12)
C7—C8—C12—C11	−179.72 (17)	C2B'—C6B—N4B—C5B	178.3 (12)
C10—C11—C12—C8	−0.1 (2)	N4B'—C5B—N4B—C2B	6.7 (8)
C11—C10—N13—O14	−178.84 (19)	N4B'—C5B—N4B—C6B	−173.4 (9)
O9—C10—N13—O14	−1.0 (2)	C2B—O1B—C2B'—N4B'	3.5 (7)
C11—C10—N13—O15	0.9 (3)	C2B—O1B—C2B'—C6B	−175 (3)
O9—C10—N13—O15	178.66 (15)	N4B—C6B—C2B'—O1B	173 (3)
C2A'—O1A—C2A—N4A	3.3 (15)	N4B—C6B—C2B'—N4B'	−4.9 (7)
C2A'—O1A—C2A—C3A	−176.8 (15)	O1B—C2B'—N4B'—C3B	−1 (2)
N4A'—C3A—C2A—O1A	175.5 (14)	C6B—C2B'—N4B'—C3B	177.7 (10)
N4A'—C3A—C2A—N4A	−4.6 (14)	O1B—C2B'—N4B'—C5B	−172.3 (11)
O1A—C2A—N4A—C6A	−1.8 (3)	C6B—C2B'—N4B'—C5B	6.3 (18)
C3A—C2A—N4A—C6A	178.29 (18)	C2B—C3B—N4B'—C2B'	−2.4 (9)
O1A—C2A—N4A—C5A	−177.25 (19)	C2B—C3B—N4B'—C5B	166 (2)
C3A—C2A—N4A—C5A	2.8 (3)	N4B—C5B—N4B'—C2B'	−0.4 (9)
C2A'—C6A—N4A—C2A	−1.8 (13)	N4B—C5B—N4B'—C3B	−169 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1B	0.95 (3)	1.81 (3)	2.7463 (19)	169 (3)
C7—H7···O1A	0.95	2.30	3.175 (2)	152

(II) 2,6-diacetaminopyridine dimethylformamide monosolvate

Crystal data

C9H11N3O2·C3H7NO	F(000) = 568
Mr = 266.30	Dx = 1.270 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.3031 (7) Å	Cell parameters from 6874 reflections
b = 13.1539 (8) Å	θ = 3.3–25.9°
c = 9.3959 (5) Å	µ = 0.09 mm^−1
β = 94.327 (5)°	T = 173 K
V = 1393.00 (14) Å^3	Block, colourless
Z = 4	0.50 × 0.40 × 0.40 mm

Data collection

Stoe IPDS II two-circle diffractometer	1967 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.100
Graphite monochromator	θmax = 25.6°, θmin = 3.3°
ω scans	h = −13→13
12406 measured reflections	k = −15→15
2603 independent reflections	l = −10→11

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0587P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
2603 reflections	Δρmax = 0.24 e Å^−3
187 parameters	Δρmin = −0.19 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.81887 (10)	0.42930 (9)	0.33685 (12)	0.0280 (3)
C2	0.77593 (12)	0.52246 (11)	0.30726 (16)	0.0299 (3)
C3	0.77636 (13)	0.59988 (11)	0.40791 (17)	0.0356 (4)
H3	0.7454	0.6653	0.3838	0.043*
C4	0.82346 (14)	0.57795 (12)	0.54412 (17)	0.0372 (4)
H4	0.8245	0.6291	0.6156	0.045*
C5	0.86915 (13)	0.48275 (12)	0.57834 (16)	0.0340 (4)
H5	0.9016	0.4672	0.6720	0.041*
C6	0.86552 (12)	0.41064 (11)	0.46952 (15)	0.0278 (3)
N21	0.72814 (12)	0.53106 (10)	0.16546 (14)	0.0347 (3)
H21	0.7197 (16)	0.4710 (17)	0.118 (2)	0.053 (5)*
C22	0.69884 (14)	0.61764 (12)	0.09140 (18)	0.0371 (4)
C23	0.64755 (17)	0.59993 (13)	−0.05894 (19)	0.0469 (4)
H23A	0.5641	0.6209	−0.0674	0.070*	0.42 (5)
H23B	0.6532	0.5276	−0.0822	0.070*	0.42 (5)
H23C	0.6919	0.6398	−0.1251	0.070*	0.42 (5)
H23D	0.5674	0.5718	−0.0572	0.070*	0.58 (5)
H23E	0.6978	0.5519	−0.1067	0.070*	0.58 (5)
H23F	0.6440	0.6646	−0.1111	0.070*	0.58 (5)
O24	0.71192 (12)	0.70272 (9)	0.14172 (14)	0.0516 (3)
N61	0.91380 (11)	0.31284 (10)	0.48319 (13)	0.0285 (3)
H61	0.9215 (15)	0.2810 (14)	0.404 (2)	0.042 (5)*
C62	0.95180 (12)	0.26280 (12)	0.60424 (15)	0.0310 (3)
C63	1.00524 (16)	0.16042 (13)	0.58083 (17)	0.0428 (4)
H63A	1.0861	0.1584	0.6265	0.064*	0.66 (2)
H63B	1.0075	0.1481	0.4782	0.064*	0.66 (2)
H63C	0.9571	0.1078	0.6225	0.064*	0.66 (2)
H63D	0.9488	0.1187	0.5220	0.064*	0.34 (2)
H63E	1.0236	0.1270	0.6731	0.064*	0.34 (2)
H63F	1.0783	0.1686	0.5320	0.064*	0.34 (2)
O64	0.94306 (11)	0.29781 (8)	0.72423 (11)	0.0419 (3)
O1A	0.66772 (10)	0.34158 (9)	0.02033 (13)	0.0424 (3)
C2A	0.65996 (13)	0.26859 (12)	0.10092 (17)	0.0345 (4)
H2A	0.7024	0.2723	0.1920	0.041*
N3A	0.59688 (11)	0.18486 (10)	0.07072 (14)	0.0342 (3)
C4A	0.59146 (16)	0.10297 (13)	0.1735 (2)	0.0453 (4)
H4A1	0.6417	0.1197	0.2599	0.068*
H4A2	0.6196	0.0399	0.1321	0.068*
H4A3	0.5093	0.0940	0.1980	0.068*
C5A	0.53209 (15)	0.17015 (14)	−0.06731 (19)	0.0428 (4)
H5A1	0.5349	0.2328	−0.1234	0.064*
H5A2	0.4493	0.1532	−0.0534	0.064*
H5A3	0.5684	0.1146	−0.1182	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0304 (6)	0.0251 (6)	0.0284 (6)	−0.0028 (5)	0.0007 (5)	−0.0004 (5)
C2	0.0282 (7)	0.0259 (8)	0.0354 (8)	−0.0036 (5)	0.0021 (6)	0.0004 (6)
C3	0.0358 (8)	0.0253 (8)	0.0462 (9)	−0.0023 (6)	0.0060 (7)	−0.0044 (7)
C4	0.0425 (9)	0.0316 (8)	0.0381 (9)	−0.0051 (6)	0.0075 (7)	−0.0105 (6)
C5	0.0372 (8)	0.0364 (9)	0.0286 (8)	−0.0047 (6)	0.0035 (6)	−0.0047 (6)
C6	0.0274 (7)	0.0289 (7)	0.0274 (7)	−0.0048 (5)	0.0037 (6)	−0.0013 (6)
N21	0.0427 (7)	0.0242 (7)	0.0357 (7)	0.0002 (5)	−0.0061 (5)	0.0000 (5)
C22	0.0363 (8)	0.0267 (8)	0.0477 (10)	0.0003 (6)	−0.0007 (7)	0.0054 (7)
C23	0.0551 (10)	0.0372 (9)	0.0465 (10)	0.0033 (8)	−0.0091 (8)	0.0091 (7)
O24	0.0676 (8)	0.0265 (7)	0.0586 (8)	0.0007 (5)	−0.0088 (6)	0.0036 (5)
N61	0.0360 (7)	0.0288 (7)	0.0203 (6)	−0.0005 (5)	0.0008 (5)	−0.0009 (5)
C62	0.0316 (7)	0.0371 (8)	0.0243 (7)	−0.0056 (6)	0.0013 (6)	0.0025 (6)
C63	0.0500 (9)	0.0470 (10)	0.0315 (8)	0.0106 (8)	0.0025 (7)	0.0089 (7)
O64	0.0614 (7)	0.0420 (7)	0.0222 (5)	−0.0067 (5)	0.0020 (5)	0.0004 (5)
O1A	0.0511 (7)	0.0322 (6)	0.0429 (6)	−0.0061 (5)	−0.0026 (5)	0.0009 (5)
C2A	0.0326 (8)	0.0333 (8)	0.0374 (8)	0.0022 (6)	0.0009 (6)	−0.0049 (7)
N3A	0.0352 (7)	0.0299 (7)	0.0375 (7)	−0.0008 (5)	0.0024 (5)	−0.0024 (5)
C4A	0.0518 (10)	0.0349 (9)	0.0498 (10)	−0.0012 (7)	0.0081 (8)	0.0040 (7)
C5A	0.0401 (9)	0.0434 (10)	0.0442 (9)	−0.0063 (7)	−0.0013 (7)	−0.0088 (7)

Geometric parameters (Å, º)

N1—C6	1.3390 (19)	N61—C62	1.3556 (19)
N1—C2	1.3395 (19)	N61—H61	0.87 (2)
C2—C3	1.389 (2)	C62—O64	1.2287 (18)
C2—N21	1.404 (2)	C62—C63	1.499 (2)
C3—C4	1.379 (2)	C63—H63A	0.9800
C3—H3	0.9500	C63—H63B	0.9800
C4—C5	1.383 (2)	C63—H63C	0.9800
C4—H4	0.9500	C63—H63D	0.9801
C5—C6	1.393 (2)	C63—H63E	0.9801
C5—H5	0.9500	C63—H63F	0.9801
C6—N61	1.3995 (19)	O1A—C2A	1.2300 (19)
N21—C22	1.362 (2)	C2A—N3A	1.331 (2)
N21—H21	0.91 (2)	C2A—H2A	0.9500
C22—O24	1.220 (2)	N3A—C4A	1.451 (2)
C22—C23	1.504 (2)	N3A—C5A	1.453 (2)
C23—H23A	0.9800	C4A—H4A1	0.9800
C23—H23B	0.9800	C4A—H4A2	0.9800
C23—H23C	0.9800	C4A—H4A3	0.9800
C23—H23D	0.9804	C5A—H5A1	0.9800
C23—H23E	0.9804	C5A—H5A2	0.9800
C23—H23F	0.9805	C5A—H5A3	0.9800
C6—N1—C2	118.16 (12)	C62—N61—H61	116.3 (12)
N1—C2—C3	123.14 (14)	C6—N61—H61	115.3 (12)
N1—C2—N21	112.22 (13)	O64—C62—N61	123.06 (14)
C3—C2—N21	124.62 (14)	O64—C62—C63	122.18 (13)
C4—C3—C2	117.36 (14)	N61—C62—C63	114.76 (13)
C4—C3—H3	121.3	C62—C63—H63A	109.5
C2—C3—H3	121.3	C62—C63—H63B	109.5
C3—C4—C5	121.09 (14)	C62—C63—H63C	109.5
C3—C4—H4	119.5	C62—C63—H63D	109.5
C5—C4—H4	119.5	C62—C63—H63E	109.5
C4—C5—C6	117.13 (14)	H63D—C63—H63E	109.5
C4—C5—H5	121.4	C62—C63—H63F	109.5
C6—C5—H5	121.4	H63D—C63—H63F	109.5
N1—C6—C5	123.11 (14)	H63E—C63—H63F	109.5
N1—C6—N61	112.17 (12)	O1A—C2A—N3A	125.21 (15)
C5—C6—N61	124.67 (13)	O1A—C2A—H2A	117.4
C22—N21—C2	127.83 (14)	N3A—C2A—H2A	117.4
C22—N21—H21	117.5 (13)	C2A—N3A—C4A	121.41 (14)
C2—N21—H21	114.6 (13)	C2A—N3A—C5A	121.75 (14)
O24—C22—N21	123.46 (16)	C4A—N3A—C5A	116.83 (14)
O24—C22—C23	122.22 (15)	N3A—C4A—H4A1	109.5
N21—C22—C23	114.32 (14)	N3A—C4A—H4A2	109.5
C22—C23—H23A	109.5	H4A1—C4A—H4A2	109.5
C22—C23—H23B	109.5	N3A—C4A—H4A3	109.5
C22—C23—H23C	109.5	H4A1—C4A—H4A3	109.5
C22—C23—H23D	109.5	H4A2—C4A—H4A3	109.5
C22—C23—H23E	109.5	N3A—C5A—H5A1	109.5
H23D—C23—H23E	109.4	N3A—C5A—H5A2	109.5
C22—C23—H23F	109.5	H5A1—C5A—H5A2	109.5
H23D—C23—H23F	109.4	N3A—C5A—H5A3	109.5
H23E—C23—H23F	109.4	H5A1—C5A—H5A3	109.5
C62—N61—C6	128.32 (13)	H5A2—C5A—H5A3	109.5
C6—N1—C2—C3	−0.8 (2)	N1—C2—N21—C22	−165.90 (14)
C6—N1—C2—N21	−179.05 (12)	C3—C2—N21—C22	15.8 (2)
N1—C2—C3—C4	−0.1 (2)	C2—N21—C22—O24	0.5 (3)
N21—C2—C3—C4	177.94 (14)	C2—N21—C22—C23	−179.08 (14)
C2—C3—C4—C5	0.5 (2)	N1—C6—N61—C62	−169.19 (13)
C3—C4—C5—C6	0.1 (2)	C5—C6—N61—C62	13.4 (2)
C2—N1—C6—C5	1.4 (2)	C6—N61—C62—O64	3.5 (2)
C2—N1—C6—N61	−176.13 (11)	C6—N61—C62—C63	−176.79 (13)
C4—C5—C6—N1	−1.0 (2)	O1A—C2A—N3A—C4A	−179.06 (14)
C4—C5—C6—N61	176.14 (13)	O1A—C2A—N3A—C5A	2.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O1A	0.91 (2)	2.00 (2)	2.8979 (18)	168.8 (17)
N61—H61···O64^i	0.87 (2)	2.01 (2)	2.8757 (16)	177.4 (18)

Symmetry code: (i) x, −y+1/2, z−1/2.

(I.II) (E)-1-[(5-nitro-2-furyl)methylideneamino]imidazolidine-2,4-dione–2,6- diacetaminopyridine (1/1)

Crystal data

C8H6N4O5·C9H11N3O2	F(000) = 896
Mr = 431.38	Dx = 1.490 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.8407 (6) Å	Cell parameters from 18548 reflections
b = 17.9443 (10) Å	θ = 3.5–25.8°
c = 10.9902 (6) Å	µ = 0.12 mm^−1
β = 97.839 (5)°	T = 173 K
V = 1922.56 (19) Å^3	Block, colourless
Z = 4	0.50 × 0.50 × 0.40 mm

Data collection

Stoe IPDS II two-circle diffractometer	2802 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.138
Graphite monochromator	θmax = 25.6°, θmin = 3.5°
ω scans	h = −11→11
32493 measured reflections	k = −21→21
3619 independent reflections	l = −12→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.122	w = 1/[σ^2(Fo^2) + (0.0793P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.004
3619 reflections	Δρmax = 0.24 e Å^−3
295 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.52583 (13)	0.64458 (7)	0.64174 (13)	0.0296 (3)
C2	0.42350 (17)	0.68120 (9)	0.68671 (16)	0.0301 (4)
C3	0.41884 (18)	0.75887 (9)	0.69434 (17)	0.0349 (4)
H3	0.3473	0.7835	0.7284	0.042*
C4	0.52252 (18)	0.79852 (10)	0.65029 (17)	0.0384 (4)
H4	0.5217	0.8514	0.6537	0.046*
C5	0.62753 (18)	0.76271 (9)	0.60124 (17)	0.0357 (4)
H5	0.6973	0.7900	0.5691	0.043*
C6	0.62646 (16)	0.68500 (9)	0.60097 (16)	0.0298 (4)
N21	0.32474 (15)	0.63422 (8)	0.72663 (15)	0.0356 (4)
H21	0.337 (2)	0.5827 (12)	0.7193 (18)	0.043 (5)*
C22	0.20514 (18)	0.65339 (10)	0.77066 (19)	0.0397 (4)
C23	0.11866 (19)	0.58871 (11)	0.8009 (2)	0.0494 (5)
H23A	0.0935	0.5954	0.8835	0.074*
H23B	0.1708	0.5424	0.7980	0.074*
H23C	0.0353	0.5863	0.7410	0.074*
O24	0.17032 (16)	0.71770 (8)	0.78528 (18)	0.0658 (5)
N61	0.72765 (14)	0.64156 (8)	0.55533 (14)	0.0332 (3)
H61	0.713 (2)	0.5936 (13)	0.548 (2)	0.050 (6)*
C62	0.85420 (17)	0.66453 (10)	0.52916 (18)	0.0380 (4)
C63	0.9342 (2)	0.60583 (11)	0.4720 (2)	0.0475 (5)
H63A	0.8942	0.5984	0.3862	0.071*
H63B	0.9306	0.5589	0.5171	0.071*
H63C	1.0298	0.6219	0.4754	0.071*
O64	0.89694 (15)	0.72777 (8)	0.55051 (17)	0.0608 (5)
N1'	0.54265 (14)	0.48520 (8)	0.65571 (14)	0.0328 (4)
H1'	0.537 (2)	0.5339 (13)	0.6433 (19)	0.050 (6)*
C2'	0.64290 (17)	0.44362 (8)	0.60760 (16)	0.0308 (4)
O21'	0.72697 (12)	0.46849 (6)	0.54699 (12)	0.0386 (3)
N3'	0.62300 (14)	0.37095 (7)	0.64226 (14)	0.0311 (3)
C4'	0.50642 (16)	0.36282 (8)	0.71095 (16)	0.0293 (4)
H4'1	0.5354	0.3428	0.7944	0.035*
H4'2	0.4346	0.3302	0.6673	0.035*
C5'	0.45734 (17)	0.44286 (9)	0.71532 (16)	0.0315 (4)
O51'	0.35997 (13)	0.46560 (7)	0.76174 (13)	0.0412 (3)
N6'	0.70088 (14)	0.31481 (7)	0.60336 (13)	0.0296 (3)
C7'	0.66610 (16)	0.24868 (9)	0.63244 (16)	0.0295 (4)
H7'	0.5906	0.2411	0.6764	0.035*
C8'	0.74453 (16)	0.18599 (8)	0.59668 (16)	0.0290 (4)
O9'	0.69141 (11)	0.11784 (6)	0.62218 (11)	0.0326 (3)
C10'	0.77851 (17)	0.06735 (8)	0.58329 (17)	0.0316 (4)
C11'	0.88363 (18)	0.09948 (9)	0.53549 (17)	0.0331 (4)
H11'	0.9568	0.0752	0.5034	0.040*
C12'	0.86101 (17)	0.17743 (9)	0.54369 (17)	0.0331 (4)
H12'	0.9163	0.2160	0.5174	0.040*
N13'	0.74296 (15)	−0.00858 (8)	0.59716 (15)	0.0376 (4)
O14'	0.63803 (15)	−0.02321 (7)	0.64050 (17)	0.0651 (5)
O15'	0.82215 (13)	−0.05616 (6)	0.56451 (13)	0.0448 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0277 (7)	0.0235 (6)	0.0391 (8)	0.0008 (5)	0.0095 (6)	0.0014 (6)
C2	0.0302 (8)	0.0246 (8)	0.0364 (9)	0.0012 (6)	0.0079 (7)	−0.0019 (7)
C3	0.0361 (9)	0.0248 (8)	0.0445 (11)	0.0038 (7)	0.0085 (8)	−0.0033 (7)
C4	0.0447 (10)	0.0221 (8)	0.0481 (11)	0.0001 (7)	0.0052 (9)	0.0001 (7)
C5	0.0358 (9)	0.0261 (8)	0.0458 (11)	−0.0039 (7)	0.0075 (8)	0.0036 (7)
C6	0.0272 (8)	0.0263 (8)	0.0365 (9)	−0.0008 (6)	0.0060 (7)	0.0015 (7)
N21	0.0309 (7)	0.0245 (7)	0.0548 (10)	0.0031 (6)	0.0184 (7)	−0.0013 (6)
C22	0.0302 (9)	0.0384 (10)	0.0532 (12)	0.0087 (8)	0.0158 (8)	0.0033 (8)
C23	0.0327 (10)	0.0447 (11)	0.0751 (15)	0.0050 (8)	0.0223 (10)	0.0066 (10)
O24	0.0575 (9)	0.0364 (8)	0.1135 (14)	0.0176 (7)	0.0478 (9)	0.0051 (8)
N61	0.0287 (7)	0.0260 (7)	0.0472 (9)	−0.0015 (6)	0.0137 (6)	0.0022 (6)
C62	0.0304 (9)	0.0381 (10)	0.0475 (11)	−0.0033 (7)	0.0127 (8)	0.0065 (8)
C63	0.0370 (10)	0.0454 (11)	0.0647 (14)	0.0015 (8)	0.0231 (10)	0.0041 (10)
O64	0.0432 (8)	0.0428 (8)	0.1021 (13)	−0.0155 (6)	0.0313 (8)	−0.0097 (8)
N1'	0.0325 (8)	0.0191 (7)	0.0503 (10)	0.0024 (6)	0.0183 (7)	0.0038 (6)
C2'	0.0305 (8)	0.0218 (8)	0.0414 (10)	0.0004 (7)	0.0096 (7)	0.0009 (7)
O21'	0.0367 (7)	0.0256 (6)	0.0581 (8)	0.0004 (5)	0.0230 (6)	0.0045 (5)
N3'	0.0313 (7)	0.0190 (6)	0.0462 (9)	0.0009 (5)	0.0172 (6)	−0.0001 (6)
C4'	0.0284 (8)	0.0222 (7)	0.0397 (9)	−0.0006 (6)	0.0131 (7)	−0.0001 (7)
C5'	0.0303 (8)	0.0267 (8)	0.0390 (10)	0.0008 (7)	0.0106 (7)	0.0012 (7)
O51'	0.0386 (7)	0.0310 (6)	0.0588 (9)	0.0066 (5)	0.0239 (6)	0.0047 (6)
N6'	0.0290 (7)	0.0204 (7)	0.0406 (8)	0.0031 (5)	0.0090 (6)	−0.0018 (6)
C7'	0.0270 (8)	0.0225 (8)	0.0404 (10)	0.0003 (6)	0.0096 (7)	−0.0002 (7)
C8'	0.0306 (8)	0.0194 (7)	0.0377 (9)	−0.0014 (6)	0.0072 (7)	0.0018 (7)
O9'	0.0287 (6)	0.0199 (5)	0.0518 (8)	0.0018 (4)	0.0147 (5)	0.0002 (5)
C10'	0.0304 (8)	0.0217 (8)	0.0440 (10)	0.0043 (6)	0.0096 (7)	−0.0015 (7)
C11'	0.0309 (8)	0.0283 (9)	0.0423 (10)	0.0034 (7)	0.0134 (7)	−0.0013 (7)
C12'	0.0319 (9)	0.0255 (8)	0.0437 (10)	−0.0002 (6)	0.0120 (8)	0.0009 (7)
N13'	0.0354 (8)	0.0217 (7)	0.0571 (10)	0.0021 (6)	0.0108 (7)	−0.0005 (7)
O14'	0.0537 (9)	0.0265 (7)	0.1245 (15)	−0.0029 (6)	0.0463 (9)	0.0034 (8)
O15'	0.0446 (7)	0.0242 (6)	0.0658 (9)	0.0096 (5)	0.0088 (7)	−0.0046 (6)

Geometric parameters (Å, º)

N1—C2	1.351 (2)	N1'—C5'	1.364 (2)
N1—C6	1.352 (2)	N1'—C2'	1.397 (2)
C2—C3	1.397 (2)	N1'—H1'	0.88 (2)
C2—N21	1.401 (2)	C2'—O21'	1.216 (2)
C3—C4	1.384 (3)	C2'—N3'	1.380 (2)
C3—H3	0.9500	N3'—N6'	1.3691 (19)
C4—C5	1.387 (3)	N3'—C4'	1.464 (2)
C4—H4	0.9500	C4'—C5'	1.518 (2)
C5—C6	1.395 (2)	C4'—H4'1	0.9900
C5—H5	0.9500	C4'—H4'2	0.9900
C6—N61	1.410 (2)	C5'—O51'	1.216 (2)
N21—C22	1.376 (2)	N6'—C7'	1.287 (2)
N21—H21	0.94 (2)	C7'—C8'	1.449 (2)
C22—O24	1.221 (2)	C7'—H7'	0.9500
C22—C23	1.503 (3)	C8'—C12'	1.363 (2)
C23—H23A	0.9800	C8'—O9'	1.3739 (19)
C23—H23B	0.9800	O9'—C10'	1.3557 (19)
C23—H23C	0.9800	C10'—C11'	1.352 (2)
N61—C62	1.379 (2)	C10'—N13'	1.420 (2)
N61—H61	0.88 (2)	C11'—C12'	1.421 (2)
C62—O64	1.222 (2)	C11'—H11'	0.9500
C62—C63	1.503 (3)	C12'—H12'	0.9500
C63—H63A	0.9800	N13'—O14'	1.223 (2)
C63—H63B	0.9800	N13'—O15'	1.2415 (18)
C63—H63C	0.9800
C2—N1—C6	118.44 (14)	H63B—C63—H63C	109.5
N1—C2—C3	122.63 (15)	C5'—N1'—C2'	113.39 (13)
N1—C2—N21	113.91 (14)	C5'—N1'—H1'	126.7 (14)
C3—C2—N21	123.45 (15)	C2'—N1'—H1'	119.9 (14)
C4—C3—C2	117.38 (16)	O21'—C2'—N3'	129.12 (15)
C4—C3—H3	121.3	O21'—C2'—N1'	125.44 (14)
C2—C3—H3	121.3	N3'—C2'—N1'	105.43 (14)
C3—C4—C5	121.43 (16)	N6'—N3'—C2'	120.18 (13)
C3—C4—H4	119.3	N6'—N3'—C4'	126.80 (12)
C5—C4—H4	119.3	C2'—N3'—C4'	112.77 (13)
C4—C5—C6	117.28 (16)	N3'—C4'—C5'	101.37 (12)
C4—C5—H5	121.4	N3'—C4'—H4'1	111.5
C6—C5—H5	121.4	C5'—C4'—H4'1	111.5
N1—C6—C5	122.78 (15)	N3'—C4'—H4'2	111.5
N1—C6—N61	113.96 (14)	C5'—C4'—H4'2	111.5
C5—C6—N61	123.24 (15)	H4'1—C4'—H4'2	109.3
C22—N21—C2	128.52 (15)	O51'—C5'—N1'	125.91 (15)
C22—N21—H21	113.8 (12)	O51'—C5'—C4'	127.09 (15)
C2—N21—H21	117.6 (12)	N1'—C5'—C4'	107.00 (13)
O24—C22—N21	123.48 (17)	C7'—N6'—N3'	114.94 (14)
O24—C22—C23	121.56 (16)	N6'—C7'—C8'	118.61 (14)
N21—C22—C23	114.97 (16)	N6'—C7'—H7'	120.7
C22—C23—H23A	109.5	C8'—C7'—H7'	120.7
C22—C23—H23B	109.5	C12'—C8'—O9'	110.63 (13)
H23A—C23—H23B	109.5	C12'—C8'—C7'	135.52 (14)
C22—C23—H23C	109.5	O9'—C8'—C7'	113.84 (13)
H23A—C23—H23C	109.5	C10'—O9'—C8'	104.83 (12)
H23B—C23—H23C	109.5	C11'—C10'—O9'	112.82 (14)
C62—N61—C6	127.66 (15)	C11'—C10'—N13'	131.59 (15)
C62—N61—H61	114.7 (15)	O9'—C10'—N13'	115.58 (14)
C6—N61—H61	117.4 (15)	C10'—C11'—C12'	105.09 (15)
O64—C62—N61	122.31 (17)	C10'—C11'—H11'	127.5
O64—C62—C63	123.03 (16)	C12'—C11'—H11'	127.5
N61—C62—C63	114.65 (16)	C8'—C12'—C11'	106.63 (14)
C62—C63—H63A	109.5	C8'—C12'—H12'	126.7
C62—C63—H63B	109.5	C11'—C12'—H12'	126.7
H63A—C63—H63B	109.5	O14'—N13'—O15'	124.15 (14)
C62—C63—H63C	109.5	O14'—N13'—C10'	118.76 (14)
H63A—C63—H63C	109.5	O15'—N13'—C10'	117.09 (15)
C6—N1—C2—C3	−1.0 (2)	N6'—N3'—C4'—C5'	−175.01 (15)
C6—N1—C2—N21	−179.90 (14)	C2'—N3'—C4'—C5'	−0.76 (19)
N1—C2—C3—C4	1.8 (3)	C2'—N1'—C5'—O51'	−177.74 (17)
N21—C2—C3—C4	−179.38 (16)	C2'—N1'—C5'—C4'	1.6 (2)
C2—C3—C4—C5	−0.4 (3)	N3'—C4'—C5'—O51'	178.85 (18)
C3—C4—C5—C6	−1.6 (3)	N3'—C4'—C5'—N1'	−0.51 (18)
C2—N1—C6—C5	−1.3 (2)	C2'—N3'—N6'—C7'	−174.43 (16)
C2—N1—C6—N61	−179.64 (14)	C4'—N3'—N6'—C7'	−0.6 (2)
C4—C5—C6—N1	2.5 (3)	N3'—N6'—C7'—C8'	−178.99 (14)
C4—C5—C6—N61	−179.23 (16)	N6'—C7'—C8'—C12'	6.2 (3)
N1—C2—N21—C22	−176.25 (17)	N6'—C7'—C8'—O9'	−174.36 (15)
C3—C2—N21—C22	4.8 (3)	C12'—C8'—O9'—C10'	−0.03 (19)
C2—N21—C22—O24	−2.8 (3)	C7'—C8'—O9'—C10'	−179.58 (14)
C2—N21—C22—C23	177.57 (18)	C8'—O9'—C10'—C11'	0.3 (2)
N1—C6—N61—C62	−166.82 (16)	C8'—O9'—C10'—N13'	−178.46 (15)
C5—C6—N61—C62	14.8 (3)	O9'—C10'—C11'—C12'	−0.5 (2)
C6—N61—C62—O64	4.3 (3)	N13'—C10'—C11'—C12'	178.06 (19)
C6—N61—C62—C63	−175.34 (17)	O9'—C8'—C12'—C11'	−0.3 (2)
C5'—N1'—C2'—O21'	177.07 (17)	C7'—C8'—C12'—C11'	179.15 (19)
C5'—N1'—C2'—N3'	−2.1 (2)	C10'—C11'—C12'—C8'	0.4 (2)
O21'—C2'—N3'—N6'	−2.7 (3)	C11'—C10'—N13'—O14'	−177.6 (2)
N1'—C2'—N3'—N6'	176.37 (14)	O9'—C10'—N13'—O14'	1.0 (3)
O21'—C2'—N3'—C4'	−177.41 (18)	C11'—C10'—N13'—O15'	2.8 (3)
N1'—C2'—N3'—C4'	1.70 (19)	O9'—C10'—N13'—O15'	−178.68 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···O51′	0.94 (2)	2.16 (2)	3.0640 (19)	162.4 (17)
N61—H61···O21′	0.88 (2)	2.25 (2)	3.1069 (19)	167 (2)
N1′—H1′···N1	0.88 (2)	1.99 (2)	2.868 (2)	171.6 (19)
C7′—H7′···O24^i	0.95	2.69	3.592 (2)	159

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.