Polymorphism of urea–barbituric acid co-crystals

Gryl, M.; Krawczuk, A.; Stadnicka, K.

doi:10.1107/S0108768108026645

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Polymorphism of urea-barbituric acid co-crystals

M. Gryl, A. Krawczuk and K. Stadnicka

The crystal structures of three polymorphs found for the addition complex of urea and barbituric acid are described and compared. Two polymorphs are monoclinic, space groups P2₁/c and Cc, whereas the third is triclinic, $P\bar 1$ . The displacement of electron density towards the mesomeric forms, corresponding to the tautomeric forms of higher stability, of the barbituric acid molecule seem to influence the type of hydrogen bonds formed, which in turn determines the different packing topology in the polymorphs. While the polymorphic forms can be easily differentiated at the first-level graph-set analysis of their hydrogen-bonding patterns, a higher-level analysis enables important features of the mutual spatial arrangement of the structural components to be revealed.

Keywords: addition compounds; polymorphism; hydrogen bonding; graph-set analysis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768108026645/bs5065sup1.cif Contains datablocks global, I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108026645/bs5065Isup2.fcf Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108026645/bs5065IIsup3.fcf Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768108026645/bs5065IIIsup4.fcf Contains datablock III

CCDC references: 705613; 705614; 705615

Computing details top

For all compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); ORTEP-3 for Windows (Farrugia, 1997); Mercury (Version 1.4; Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

(I) 2,4,6(1H,3H,5H)-Pyrimidinetrione urea addition compound top

Crystal data top

C₅H₈N₄O₄	F(000) = 392
M_r = 188.15	D_x = 1.593 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1657 reflections
a = 7.8857 (3) Å	θ = 1.0–27.5°
b = 6.9620 (2) Å	µ = 0.14 mm⁻¹
c = 14.4283 (6) Å	T = 293 K
β = 98.027 (1)°	Plate, yellowish
V = 784.36 (5) Å³	0.30 × 0.22 × 0.05 mm
Z = 4

Data collection top

KappaCCD diffractometer	1775 independent reflections
Radiation source: fine-focus sealed tube	1334 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.025
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans at χ = 55 °	h = −10→10
Absorption correction: multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	k = −9→8
T_min = 0.960, T_max = 0.993	l = −18→18
3177 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0535P)² + 0.1825P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.21 e Å⁻³
1775 reflections	Δρ_min = −0.19 e Å⁻³
118 parameters

Crystal data top

C₅H₈N₄O₄	V = 784.36 (5) Å³
M_r = 188.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8857 (3) Å	µ = 0.14 mm⁻¹
b = 6.9620 (2) Å	T = 293 K
c = 14.4283 (6) Å	0.30 × 0.22 × 0.05 mm
β = 98.027 (1)°

Data collection top

KappaCCD diffractometer	1775 independent reflections
Absorption correction: multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	1334 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.993	R_int = 0.025
3177 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
1775 reflections	Δρ_min = −0.19 e Å⁻³
118 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.29444 (13)	0.08443 (15)	−0.04154 (8)	0.0405 (3)
C1	0.33939 (19)	0.2365 (2)	0.00107 (11)	0.0312 (4)
N2	0.49808 (17)	0.2593 (2)	0.04500 (11)	0.0453 (4)
H2A	0.5718	0.1684	0.0444	0.054*
H2B	0.5269	0.3648	0.0740	0.054*
N4	0.22878 (18)	0.3807 (2)	0.00349 (12)	0.0490 (4)
H4A	0.1255	0.3695	−0.0244	0.059*
H4B	0.2607	0.4848	0.0329	0.059*
N1	0.02901 (15)	0.02606 (18)	0.12628 (9)	0.0316 (3)
H1	−0.0651	0.0085	0.0893	0.038*
C2	0.15042 (18)	−0.1145 (2)	0.12890 (11)	0.0320 (4)
O2	0.12314 (14)	−0.26446 (16)	0.08623 (9)	0.0477 (4)
N3	0.30640 (15)	−0.07976 (18)	0.18238 (9)	0.0333 (3)
H3	0.3870	−0.1613	0.1785	0.040*
C4	0.34359 (18)	0.0726 (2)	0.24078 (11)	0.0319 (4)
O4	0.47961 (14)	0.08108 (17)	0.29313 (9)	0.0448 (3)
C5	0.2109 (2)	0.2251 (2)	0.23773 (12)	0.0384 (4)
H5A	0.1878	0.2463	0.3012	0.046*
H5B	0.2598	0.3430	0.2172	0.046*
C6	0.04407 (19)	0.1936 (2)	0.17773 (11)	0.0333 (4)
O6	−0.07375 (16)	0.30556 (19)	0.17366 (9)	0.0511 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0322 (6)	0.0330 (6)	0.0530 (7)	0.0027 (5)	−0.0054 (5)	−0.0115 (5)
C1	0.0313 (8)	0.0284 (8)	0.0334 (8)	−0.0004 (6)	0.0025 (6)	−0.0012 (7)
N2	0.0358 (8)	0.0341 (8)	0.0614 (10)	0.0005 (6)	−0.0098 (7)	−0.0123 (7)
N4	0.0377 (8)	0.0345 (8)	0.0721 (11)	0.0043 (6)	−0.0014 (7)	−0.0159 (7)
N1	0.0251 (6)	0.0319 (7)	0.0355 (7)	0.0023 (5)	−0.0040 (5)	−0.0031 (6)
C2	0.0281 (8)	0.0299 (8)	0.0367 (8)	−0.0005 (6)	−0.0003 (6)	−0.0012 (7)
O2	0.0371 (7)	0.0351 (7)	0.0668 (9)	0.0030 (5)	−0.0073 (6)	−0.0177 (6)
N3	0.0257 (6)	0.0289 (7)	0.0435 (7)	0.0026 (5)	−0.0008 (5)	−0.0035 (6)
C4	0.0299 (8)	0.0309 (8)	0.0338 (8)	−0.0030 (6)	0.0003 (6)	0.0028 (7)
O4	0.0347 (6)	0.0422 (7)	0.0521 (7)	−0.0021 (5)	−0.0125 (5)	−0.0007 (6)
C5	0.0386 (9)	0.0364 (9)	0.0383 (9)	0.0025 (7)	−0.0013 (7)	−0.0097 (7)
C6	0.0326 (8)	0.0348 (8)	0.0321 (8)	0.0046 (6)	0.0033 (6)	−0.0002 (7)
O6	0.0445 (7)	0.0503 (8)	0.0561 (8)	0.0184 (6)	−0.0014 (6)	−0.0131 (6)

Geometric parameters (Å, º) top

O1—C1	1.251 (2)	C2—O2	1.216 (2)
C1—N2	1.331 (2)	C2—N3	1.379 (2)
C1—N4	1.333 (2)	N3—C4	1.361 (2)
N2—H2A	0.8600	N3—H3	0.8600
N2—H2B	0.8600	C4—O4	1.224 (2)
N4—H4A	0.8600	C4—C5	1.487 (2)
N4—H4B	0.8600	C5—C6	1.487 (2)
N1—C2	1.366 (2)	C5—H5A	0.9700
N1—C6	1.378 (2)	C5—H5B	0.9700
N1—H1	0.8600	C6—O6	1.208 (2)

O1—C1—N2	121.2 (1)	C4—N3—C2	125.5 (1)
O1—C1—N4	120.6 (1)	C4—N3—H3	117.2
N2—C1—N4	118.2 (1)	C2—N3—H3	117.2
C1—N2—H2A	120.0	O4—C4—N3	120.9 (1)
C1—N2—H2B	120.0	O4—C4—C5	122.4 (1)
H2A—N2—H2B	120.0	N3—C4—C5	116.6 (1)
C1—N4—H4A	120.0	C6—C5—C4	118.3 (1)
C1—N4—H4B	120.0	C6—C5—H5A	107.7
H4A—N4—H4B	120.0	C4—C5—H5A	107.7
C2—N1—C6	125.7 (1)	C6—C5—H5B	107.7
C2—N1—H1	117.1	C4—C5—H5B	107.7
C6—N1—H1	117.1	H5A—C5—H5B	107.1
O2—C2—N1	121.8 (1)	O6—C6—N1	120.8 (1)
O2—C2—N3	121.0 (1)	O6—C6—C5	123.0 (2)
N1—C2—N3	117.2 (1)	N1—C6—C5	116.2 (1)

C6—N1—C2—O2	174.8 (2)	O4—C4—C5—C6	−174.8 (2)
C6—N1—C2—N3	−5.1 (2)	N3—C4—C5—C6	4.8 (2)
O2—C2—N3—C4	−172.2 (2)	C2—N1—C6—O6	−176.7 (2)
N1—C2—N3—C4	7.7 (2)	C2—N1—C6—C5	2.8 (2)
C2—N3—C4—O4	172.0 (2)	C4—C5—C6—O6	176.9 (2)
C2—N3—C4—C5	−7.6 (2)	C4—C5—C6—N1	−2.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.06	2.903 (2)	168
N2—H2B···O4ⁱⁱ	0.86	2.44	3.223 (2)	151
N4—H4A···O2ⁱⁱⁱ	0.86	2.17	3.005 (2)	165
N4—H4B···O2^iv	0.86	2.25	2.916 (2)	135
N1—H1···O1ⁱⁱⁱ	0.86	1.95	2.779 (2)	160
N3—H3···O4^v	0.86	2.09	2.895 (2)	156

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

(II) 2,4,6(1H,3H,5H)-Pyrimidinetrione urea addition compound top

Crystal data top

C₅H₈N₄O₄	F(000) = 392
M_r = 188.15	D_x = 1.556 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1182 reflections
a = 15.9423 (7) Å	θ = 1.0–30.0°
b = 5.0984 (3) Å	µ = 0.14 mm⁻¹
c = 10.5534 (5) Å	T = 293 K
β = 110.570 (2)°	Block, colourless
V = 803.09 (7) Å³	0.32 × 0.22 × 0.12 mm
Z = 4

Data collection top

KappaCCD diffractometer	1169 independent reflections
Radiation source: fine-focus sealed tube	1099 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.016
Detector resolution: 9 pixels mm^-1	θ_max = 30.0°, θ_min = 4.1°
ω scans at χ = 55 °	h = −21→20
Absorption correction: multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	k = −4→7
T_min = 0.958, T_max = 0.984	l = −14→14
3691 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0491P)² + 0.0769P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.033	(Δ/σ)_max < 0.001
wR(F²) = 0.083	Δρ_max = 0.15 e Å⁻³
S = 1.06	Δρ_min = −0.17 e Å⁻³
1169 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
118 parameters	Absolute structure parameter: 0.00 (3)
2 restraints

Crystal data top

C₅H₈N₄O₄	V = 803.09 (7) Å³
M_r = 188.15	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 15.9423 (7) Å	µ = 0.14 mm⁻¹
b = 5.0984 (3) Å	T = 293 K
c = 10.5534 (5) Å	0.32 × 0.22 × 0.12 mm
β = 110.570 (2)°

Data collection top

KappaCCD diffractometer	1169 independent reflections
Absorption correction: multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	1099 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.984	R_int = 0.016
3691 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.083	Δρ_max = 0.15 e Å⁻³
S = 1.06	Δρ_min = −0.17 e Å⁻³
1169 reflections	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
118 parameters	Absolute structure parameter: 0.00 (3)
2 restraints

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.76305 (8)	0.5526 (3)	0.56200 (11)	0.0355 (3)
C1	0.68332 (11)	0.4865 (4)	0.49837 (16)	0.0311 (3)
N2	0.64621 (11)	0.2830 (4)	0.53835 (17)	0.0497 (4)
H2A	0.6769	0.1945	0.6088	0.060*
H2B	0.5916	0.2403	0.4937	0.060*
N4	0.63236 (12)	0.6185 (4)	0.38989 (18)	0.0508 (5)
H4A	0.6538	0.7522	0.3619	0.061*
H4B	0.5780	0.5701	0.3477	0.061*
N1	0.84095 (10)	−0.0066 (3)	0.49126 (14)	0.0326 (3)
H1	0.8125	−0.1336	0.5117	0.039*
C2	0.80045 (10)	0.1134 (3)	0.36886 (16)	0.0314 (3)
O2	0.72846 (10)	0.0353 (3)	0.28983 (13)	0.0462 (4)
N3	0.84309 (9)	0.3242 (3)	0.33813 (13)	0.0329 (3)
H3	0.8166	0.4013	0.2620	0.039*
C4	0.92426 (10)	0.4221 (3)	0.41845 (16)	0.0320 (3)
O4	0.95950 (10)	0.6007 (3)	0.37923 (15)	0.0470 (4)
C5	0.96514 (11)	0.3047 (3)	0.55714 (16)	0.0354 (3)
H5A	1.0277	0.2683	0.5729	0.042*
H5B	0.9632	0.4353	0.6229	0.042*
C6	0.92271 (10)	0.0581 (3)	0.58379 (15)	0.0306 (3)
O6	0.95728 (9)	−0.0776 (3)	0.68302 (14)	0.0446 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0288 (6)	0.0431 (7)	0.0289 (6)	−0.0064 (5)	0.0028 (5)	−0.0013 (5)
C1	0.0285 (7)	0.0362 (8)	0.0260 (6)	−0.0022 (6)	0.0063 (5)	−0.0055 (5)
N2	0.0359 (8)	0.0574 (10)	0.0457 (9)	−0.0149 (7)	0.0016 (7)	0.0097 (8)
N4	0.0362 (8)	0.0540 (10)	0.0451 (9)	−0.0113 (7)	−0.0072 (7)	0.0129 (8)
N1	0.0286 (6)	0.0329 (6)	0.0314 (6)	−0.0052 (5)	0.0043 (5)	0.0017 (5)
C2	0.0277 (7)	0.0365 (8)	0.0273 (7)	−0.0035 (6)	0.0065 (6)	−0.0024 (6)
O2	0.0369 (7)	0.0572 (8)	0.0335 (6)	−0.0138 (6)	−0.0013 (5)	0.0014 (6)
N3	0.0323 (6)	0.0401 (7)	0.0233 (6)	−0.0030 (5)	0.0061 (5)	0.0019 (5)
C4	0.0299 (8)	0.0337 (8)	0.0312 (7)	−0.0024 (6)	0.0095 (6)	−0.0020 (6)
O4	0.0440 (7)	0.0506 (8)	0.0424 (7)	−0.0146 (6)	0.0101 (6)	0.0082 (6)
C5	0.0305 (7)	0.0385 (8)	0.0318 (8)	−0.0067 (6)	0.0041 (6)	0.0001 (6)
C6	0.0264 (7)	0.0321 (7)	0.0289 (7)	0.0005 (6)	0.0045 (6)	−0.0012 (6)
O6	0.0385 (7)	0.0435 (7)	0.0390 (7)	−0.0041 (6)	−0.0022 (5)	0.0097 (5)

Geometric parameters (Å, º) top

O1—C1	1.257 (2)	C2—O2	1.224 (2)
C1—N4	1.330 (2)	C2—N3	1.370 (2)
C1—N2	1.334 (2)	N3—C4	1.368 (2)
N2—H2A	0.8600	N3—H3	0.8600
N2—H2B	0.8600	C4—O4	1.216 (2)
N4—H4A	0.8600	C4—C5	1.502 (2)
N4—H4B	0.8600	C5—C6	1.500 (2)
N1—C6	1.366 (2)	C5—H5A	0.9700
N1—C2	1.369 (2)	C5—H5B	0.9700
N1—H1	0.8600	C6—O6	1.214 (2)

O1—C1—N4	121.4 (2)	C4—N3—C2	125.4 (1)
O1—C1—N2	121.1 (2)	C4—N3—H3	117.3
N4—C1—N2	117.5 (2)	C2—N3—H3	117.3
C1—N2—H2A	120.0	O4—C4—N3	120.8 (2)
C1—N2—H2B	120.0	O4—C4—C5	122.4 (2)
H2A—N2—H2B	120.0	N3—C4—C5	116.8 (1)
C1—N4—H4A	120.0	C6—C5—C4	116.6 (1)
C1—N4—H4B	120.0	C6—C5—H5A	108.2
H4A—N4—H4B	120.0	C4—C5—H5A	108.2
C6—N1—C2	125.6 (2)	C6—C5—H5B	108.2
C6—N1—H1	117.2	C4—C5—H5B	108.2
C2—N1—H1	117.2	H5A—C5—H5B	107.3
O2—C2—N1	121.1 (2)	O6—C6—N1	120.6 (2)
O2—C2—N3	121.2 (2)	O6—C6—C5	122.8 (1)
N1—C2—N3	117.7 (1)	N1—C6—C5	116.6 (1)

C6—N1—C2—O2	177.1 (2)	O4—C4—C5—C6	−170.2 (2)
C6—N1—C2—N3	−3.1 (2)	N3—C4—C5—C6	11.9 (2)
O2—C2—N3—C4	−178.6 (2)	C2—N1—C6—O6	−172.1 (2)
N1—C2—N3—C4	1.6 (2)	C2—N1—C6—C5	9.2 (2)
C2—N3—C4—O4	175.6 (2)	C4—C5—C6—O6	168.2 (2)
C2—N3—C4—C5	−6.4 (2)	C4—C5—C6—N1	−13.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.86	2.14	2.992 (2)	169
N2—H2B···O4ⁱⁱ	0.86	2.15	3.005 (2)	175
N4—H4A···O2ⁱⁱⁱ	0.86	2.17	3.019 (2)	169
N4—H4B···O6^iv	0.86	2.09	2.884 (2)	153
N1—H1···O1^v	0.86	1.94	2.793 (2)	172
N3—H3···O1^vi	0.86	1.99	2.811 (2)	158

Symmetry codes: (i) x, −y, z+1/2; (ii) x−1/2, y−1/2, z; (iii) x, y+1, z; (iv) x−1/2, −y+1/2, z−1/2; (v) x, y−1, z; (vi) x, −y+1, z−1/2.

(III) 2,4,6(1H,3H,5H)-Pyrimidinetrione urea addition compound top

Crystal data top

C₅H₈N₄O₄	Z = 4
M_r = 188.15	F(000) = 392
Triclinic, P1	D_x = 1.586 Mg m⁻³
a = 8.1588 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1117 (4) Å	Cell parameters from 2050 reflections
c = 10.9268 (5) Å	θ = 2.9–29.1°
α = 100.248 (2)°	µ = 0.14 mm⁻¹
β = 91.515 (2)°	T = 293 K
γ = 99.192 (2)°	Block, colourless
V = 787.82 (6) Å³	0.35 × 0.13 × 0.13 mm

Data collection top

KappaCCD diffractometer	3584 independent reflections
Radiation source: fine-focus sealed tube	2380 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	R_int = 0.017
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans at χ = 55 °	h = −9→10
Absorption correction: multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	k = −9→11
T_min = 0.953, T_max = 0.982	l = −14→14
4828 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.053	w = 1/[σ²(F_o²) + (0.0476P)² + 0.2967P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.137	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.22 e Å⁻³
3584 reflections	Δρ_min = −0.19 e Å⁻³
235 parameters

Crystal data top

C₅H₈N₄O₄	γ = 99.192 (2)°
M_r = 188.15	V = 787.82 (6) Å³
Triclinic, P1	Z = 4
a = 8.1588 (4) Å	Mo Kα radiation
b = 9.1117 (4) Å	µ = 0.14 mm⁻¹
c = 10.9268 (5) Å	T = 293 K
α = 100.248 (2)°	0.35 × 0.13 × 0.13 mm
β = 91.515 (2)°

Data collection top

KappaCCD diffractometer	3584 independent reflections
Absorption correction: multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	2380 reflections with I > 2σ(I)
T_min = 0.953, T_max = 0.982	R_int = 0.017
4828 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.03	Δρ_max = 0.22 e Å⁻³
3584 reflections	Δρ_min = −0.19 e Å⁻³
235 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1A	0.7813 (2)	0.04121 (19)	0.52443 (15)	0.0420 (4)
H1A	0.7609	0.0212	0.5971	0.050*
C2A	0.6814 (3)	−0.0434 (2)	0.42570 (18)	0.0401 (5)
O2A	0.5749 (2)	−0.14712 (17)	0.44075 (13)	0.0544 (4)
N3A	0.7088 (2)	−0.0068 (2)	0.31096 (16)	0.0463 (5)
H3A	0.6472	−0.0608	0.2489	0.056*
C4A	0.8263 (3)	0.1087 (2)	0.28616 (19)	0.0426 (5)
O4A	0.8402 (2)	0.1331 (2)	0.18121 (14)	0.0632 (5)
C5A	0.9343 (3)	0.1979 (2)	0.39424 (18)	0.0411 (5)
H5A1	1.0490	0.1935	0.3748	0.049*
H5A2	0.9197	0.3026	0.4020	0.049*
C6A	0.9096 (2)	0.1537 (2)	0.51749 (19)	0.0389 (5)
O6A	0.99946 (19)	0.21308 (18)	0.60997 (14)	0.0548 (4)
N1B	0.6821 (2)	0.42592 (19)	0.96006 (15)	0.0403 (4)
H1B	0.6549	0.4113	1.0330	0.048*
C2B	0.5979 (2)	0.3292 (2)	0.86060 (18)	0.0388 (5)
O2B	0.4860 (2)	0.22890 (18)	0.87468 (14)	0.0566 (5)
N3B	0.6444 (2)	0.34856 (19)	0.74367 (15)	0.0417 (4)
H3B	0.5977	0.2821	0.6815	0.050*
C4B	0.7586 (3)	0.4646 (2)	0.71804 (19)	0.0397 (5)
O4B	0.7809 (2)	0.47970 (19)	0.61115 (13)	0.0569 (4)
C5B	0.8523 (3)	0.5679 (3)	0.82745 (19)	0.0456 (5)
H5B1	0.8406	0.6707	0.8212	0.055*
H5B2	0.9692	0.5608	0.8208	0.055*
C6B	0.8053 (3)	0.5434 (2)	0.95412 (19)	0.0401 (5)
O6B	0.8734 (2)	0.62294 (18)	1.04861 (14)	0.0573 (5)
O1A	0.45510 (19)	0.62811 (17)	0.82492 (13)	0.0490 (4)
C1A	0.3897 (3)	0.5897 (2)	0.71742 (19)	0.0396 (5)
N2A	0.4423 (2)	0.6616 (2)	0.62667 (17)	0.0569 (5)
H2A1	0.5232	0.7366	0.6416	0.068*
H2A2	0.3955	0.6333	0.5530	0.068*
N4A	0.2615 (3)	0.4753 (2)	0.6897 (2)	0.0637 (6)
H4A1	0.2231	0.4272	0.7466	0.076*
H4A2	0.2175	0.4499	0.6149	0.076*
O1B	0.7245 (2)	−0.07543 (18)	0.73102 (13)	0.0587 (5)
C1B	0.7595 (3)	−0.0159 (2)	0.84199 (19)	0.0427 (5)
N2B	0.8721 (3)	0.1093 (2)	0.8735 (2)	0.0619 (6)
H2B1	0.9221	0.1503	0.8166	0.074*
H2B2	0.8950	0.1491	0.9507	0.074*
N4B	0.6877 (3)	−0.0768 (2)	0.93195 (17)	0.0666 (6)
H4B1	0.6158	−0.1585	0.9141	0.080*
H4B2	0.7127	−0.0348	1.0085	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0447 (10)	0.0466 (10)	0.0274 (9)	−0.0121 (8)	0.0000 (7)	0.0052 (8)
C2A	0.0411 (12)	0.0408 (11)	0.0320 (11)	−0.0066 (9)	0.0003 (9)	0.0019 (9)
O2A	0.0618 (10)	0.0527 (9)	0.0364 (8)	−0.0254 (8)	−0.0002 (7)	0.0068 (7)
N3A	0.0505 (11)	0.0467 (10)	0.0332 (9)	−0.0136 (8)	−0.0043 (8)	0.0051 (8)
C4A	0.0447 (12)	0.0456 (12)	0.0349 (11)	0.0007 (9)	0.0044 (9)	0.0064 (10)
O4A	0.0781 (12)	0.0715 (12)	0.0355 (9)	−0.0075 (9)	0.0052 (8)	0.0154 (8)
C5A	0.0381 (11)	0.0419 (11)	0.0395 (12)	−0.0064 (9)	0.0017 (9)	0.0096 (9)
C6A	0.0347 (11)	0.0393 (11)	0.0377 (11)	−0.0011 (9)	0.0021 (8)	−0.0001 (9)
O6A	0.0488 (9)	0.0623 (10)	0.0417 (9)	−0.0160 (8)	−0.0071 (7)	0.0023 (8)
N1B	0.0447 (10)	0.0444 (10)	0.0265 (8)	−0.0073 (8)	−0.0003 (7)	0.0055 (7)
C2B	0.0415 (12)	0.0403 (11)	0.0298 (10)	−0.0047 (9)	−0.0012 (8)	0.0043 (9)
O2B	0.0601 (10)	0.0607 (10)	0.0361 (8)	−0.0262 (8)	0.0018 (7)	0.0072 (7)
N3B	0.0474 (10)	0.0423 (10)	0.0274 (9)	−0.0091 (8)	−0.0004 (7)	0.0007 (7)
C4B	0.0383 (11)	0.0450 (12)	0.0348 (11)	0.0034 (9)	0.0020 (8)	0.0083 (9)
O4B	0.0663 (11)	0.0689 (11)	0.0325 (8)	−0.0049 (8)	0.0046 (7)	0.0153 (8)
C5B	0.0418 (12)	0.0503 (13)	0.0397 (12)	−0.0094 (10)	0.0000 (9)	0.0107 (10)
C6B	0.0386 (11)	0.0401 (11)	0.0371 (11)	−0.0029 (9)	−0.0030 (8)	0.0045 (9)
O6B	0.0634 (11)	0.0571 (10)	0.0382 (9)	−0.0184 (8)	−0.0084 (7)	0.0004 (8)
O1A	0.0538 (9)	0.0550 (9)	0.0318 (8)	−0.0109 (7)	−0.0038 (6)	0.0094 (7)
C1A	0.0391 (11)	0.0394 (11)	0.0372 (11)	0.0004 (9)	−0.0005 (9)	0.0043 (9)
N2A	0.0634 (13)	0.0694 (13)	0.0329 (10)	−0.0085 (10)	−0.0018 (9)	0.0139 (9)
N4A	0.0601 (13)	0.0554 (12)	0.0632 (14)	−0.0172 (10)	−0.0134 (10)	0.0041 (11)
O1B	0.0738 (11)	0.0588 (10)	0.0310 (8)	−0.0221 (8)	0.0024 (7)	0.0042 (7)
C1B	0.0490 (13)	0.0416 (12)	0.0336 (11)	−0.0022 (9)	−0.0001 (9)	0.0054 (9)
N2B	0.0639 (13)	0.0503 (12)	0.0592 (13)	−0.0143 (10)	−0.0100 (10)	0.0005 (10)
N4B	0.0990 (18)	0.0606 (13)	0.0318 (11)	−0.0134 (12)	0.0078 (10)	0.0092 (10)

Geometric parameters (Å, º) top

N1A—C6A	1.357 (2)	C4B—O4B	1.215 (2)
N1A—C2A	1.371 (2)	C4B—C5B	1.491 (3)
N1A—H1A	0.8600	C5B—C6B	1.491 (3)
C2A—O2A	1.215 (2)	C5B—H5B1	0.9700
C2A—N3A	1.368 (3)	C5B—H5B2	0.9700
N3A—C4A	1.376 (3)	C6B—O6B	1.214 (2)
N3A—H3A	0.8600	O1A—C1A	1.244 (2)
C4A—O4A	1.211 (2)	C1A—N2A	1.327 (3)
C4A—C5A	1.485 (3)	C1A—N4A	1.340 (3)
C5A—C6A	1.482 (3)	N2A—H2A1	0.8600
C5A—H5A1	0.9700	N2A—H2A2	0.8600
C5A—H5A2	0.9700	N4A—H4A1	0.8600
C6A—O6A	1.221 (2)	N4A—H4A2	0.8600
N1B—C6B	1.359 (2)	O1B—C1B	1.243 (2)
N1B—C2B	1.362 (2)	C1B—N4B	1.319 (3)
N1B—H1B	0.8600	C1B—N2B	1.331 (3)
C2B—O2B	1.218 (2)	N2B—H2B1	0.8600
C2B—N3B	1.375 (2)	N2B—H2B2	0.8600
N3B—C4B	1.367 (3)	N4B—H4B1	0.8600
N3B—H3B	0.8600	N4B—H4B2	0.8600

C6A—N1A—C2A	125.7 (2)	O4B—C4B—N3B	120.7 (2)
C6A—N1A—H1A	117.2	O4B—C4B—C5B	123.0 (2)
C2A—N1A—H1A	117.2	N3B—C4B—C5B	116.3 (2)
O2A—C2A—N3A	122.2 (2)	C4B—C5B—C6B	117.8 (2)
O2A—C2A—N1A	120.7 (2)	C4B—C5B—H5B1	107.9
N3A—C2A—N1A	117.2 (2)	C6B—C5B—H5B1	107.9
C2A—N3A—C4A	125.8 (2)	C4B—C5B—H5B2	107.9
C2A—N3A—H3A	117.1	C6B—C5B—H5B2	107.9
C4A—N3A—H3A	117.1	H5B1—C5B—H5B2	107.2
O4A—C4A—N3A	120.9 (2)	O6B—C6B—N1B	120.6 (2)
O4A—C4A—C5A	122.9 (2)	O6B—C6B—C5B	122.5 (2)
N3A—C4A—C5A	116.2 (2)	N1B—C6B—C5B	116.9 (2)
C6A—C5A—C4A	118.0 (2)	O1A—C1A—N2A	121.4 (2)
C6A—C5A—H5A1	107.8	O1A—C1A—N4A	121.0 (2)
C4A—C5A—H5A1	107.8	N2A—C1A—N4A	117.6 (2)
C6A—C5A—H5A2	107.8	C1A—N2A—H2A1	120.0
C4A—C5A—H5A2	107.8	C1A—N2A—H2A2	120.0
H5A1—C5A—H5A2	107.1	H2A1—N2A—H2A2	120.0
O6A—C6A—N1A	120.1 (2)	C1A—N4A—H4A1	120.0
O6A—C6A—C5A	122.9 (2)	C1A—N4A—H4A2	120.0
N1A—C6A—C5A	117.0 (2)	H4A1—N4A—H4A2	120.0
C6B—N1B—C2B	125.7 (2)	O1B—C1B—N4B	120.7 (2)
C6B—N1B—H1B	117.2	O1B—C1B—N2B	121.2 (2)
C2B—N1B—H1B	117.2	N4B—C1B—N2B	118.2 (2)
O2B—C2B—N1B	121.2 (2)	C1B—N2B—H2B1	120.0
O2B—C2B—N3B	121.2 (2)	C1B—N2B—H2B2	120.0
N1B—C2B—N3B	117.6 (2)	H2B1—N2B—H2B2	120.0
C4B—N3B—C2B	125.5 (2)	C1B—N4B—H4B1	120.0
C4B—N3B—H3B	117.3	C1B—N4B—H4B2	120.0
C2B—N3B—H3B	117.3	H4B1—N4B—H4B2	120.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O1B	0.86	1.85	2.682 (2)	164
N3A—H3A···O2Bⁱ	0.86	2.00	2.842 (2)	166
N1B—H1B···O1Aⁱⁱ	0.86	1.87	2.718 (2)	167
N3B—H3B···O2Aⁱ	0.86	2.01	2.842 (2)	162
N2A—H2A1···O1Bⁱⁱⁱ	0.86	2.24	3.077 (2)	165
N2A—H2A2···O4B^iv	0.86	2.25	3.088 (2)	164
N4B—H4B1···O1A^v	0.86	2.21	3.055 (3)	167
N4B—H4B2···O4A^vi	0.86	2.31	3.135 (3)	160

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

Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	C₅H₈N₄O₄	C₅H₈N₄O₄	C₅H₈N₄O₄
M_r	188.15	188.15	188.15
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, Cc	Triclinic, P1
Temperature (K)	293	293	293
a, b, c (Å)	7.8857 (3), 6.9620 (2), 14.4283 (6)	15.9423 (7), 5.0984 (3), 10.5534 (5)	8.1588 (4), 9.1117 (4), 10.9268 (5)
α, β, γ (°)	90, 98.027 (1), 90	90, 110.570 (2), 90	100.248 (2), 91.515 (2), 99.192 (2)
V (Å³)	784.36 (5)	803.09 (7)	787.82 (6)
Z	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.14	0.14	0.14
Crystal size (mm)	0.30 × 0.22 × 0.05	0.32 × 0.22 × 0.12	0.35 × 0.13 × 0.13

Data collection
Diffractometer	KappaCCD diffractometer	KappaCCD diffractometer	KappaCCD diffractometer
Absorption correction	Multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	Multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)	Multi-scan HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997)
T_min, T_max	0.960, 0.993	0.958, 0.984	0.953, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	3177, 1775, 1334	3691, 1169, 1099	4828, 3584, 2380
R_int	0.025	0.016	0.017
(sin θ/λ)_max (Å⁻¹)	0.649	0.704	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.113, 1.03	0.033, 0.083, 1.06	0.053, 0.137, 1.03
No. of reflections	1775	1169	3584
No. of parameters	118	118	235
No. of restraints	0	2	0
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.19	0.15, −0.17	0.22, −0.19
Absolute structure	?	Flack H D (1983), Acta Cryst. A39, 876-881	?
Absolute structure parameter	?	0.00 (3)	?

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003); ORTEP-3 for Windows (Farrugia, 1997); Mercury (Version 1.4; Macrae et al., 2006).

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