Hydro­gen-bonded chains in 5-methyl-2-tri­fluoro­methyl-1,2,4-triazolo­[1,5-a]­pyrimidin-7(4H)-one and hydrogen-bonded chains of rings in 5-amino-3-tri­fluoro­methyl-1H-1,2,4-triazole–5-methyl-2-tri­fluoro­methyl-1,2,4-triazolo­[1,5-a]­pyrimidin-7(4H)-one (1/1), the co-crystal of a reaction product and one of its precursors

Boechat, N.; Dutra, K.D.B.; Valverde, A.L.; Wardell, S.M.S.V.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270104020256

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 10| October 2004| Pages o733-o736

doi:10.1107/S0108270104020256

Hydrogen-bonded chains in 5-methyl-2-trifluoromethyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one and hydrogen-bonded chains of rings in 5-amino-3-trifluoromethyl-1H-1,2,4-triazole–5-methyl-2-trifluoromethyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one (1/1), the co-crystal of a reaction product and one of its precursors

Nubia Boechat,^a Karen D. B. Dutra,^a Alessandra L. Valverde,^a Solange M. S. V. Wardell,^a John N. Low ^b ‡ and Christopher Glidewell ^c ^*

^aFundação Oswaldo Cruz, Far Manguinhos, Rua Sizenando Nabuco, 100 Manguinhos, 21041250 Rio de Janeiro, RJ, Brazil, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^cSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 11 August 2004; accepted 16 August 2004; online 18 September 2004)

In the title compounds, C₇H₅F₃N₄O, (I), and C₃H₃F₃N₄·C₇H₅F₃N₄O, (II), all of the molecular components exhibit some polarization of their molecular–electronic structures. The molecules in (I) are linked into simple C(6) chains, while in (II), the components are linked by a combination of two-centre N—H⋯N and N—H⋯O, and three-centre N—H⋯(O,N) hydrogen bonds into chains containing R $[{_1^2}]$ (5), R $[{_2^1}]$ (6) and R $[{_2^2}]$ (8) rings.

Comment

In the course of our studies of fluorinated triazole precursors of potential antimalarial compounds, we needed to prepare 3-methyl-5-(trifluoromethyl)-1,2,4-triazolo[1,5-a]pyrimidin-7-one, (I). The preparation of this compound by the reaction of 5-amino-3-trifluoromethyl-1H-1,2,4-triazole with ethyl acetoacetate has recently been reported (Zohdi, 1997 ), and use of the reported chromatographic purification readily affords pure (I). However, we have found that, when purification of the crude reaction product is attempted using recrystallization methods, the crystalline material obtained is not the expected triazolopyrimidinone, (I), but a co-crystal, (II), containing a 1:1 molar ratio of (I) with the starting triazole. We report here the molecular and supramolecular structures of both (I) and the co-crystal, (II).

In both (I) and (II) (Figs. 1 and 2), the bond lengths in the six-membered rings (Tables 1 and 3) indicate that the O14—C14—C15—C16—N17 fragment constitutes a vinylogous amide, with a significant contribution from the polarized form, (Ia). The other bond distances and angles in (I) show no unexpected values. In particular, the five-membered ring of the bicyclic component shows very strong bond fixation with a clear distinction between single and double bonds.

Within the triazole component of (II), the N21—C25 and N25—C25 bonds are too similar in length to be convincingly represented as double and single bonds, respectively. In pure 5-amino-3-trifluoromethyl-1H-1,2,4-triazole itself, (III) (Borbulevych et al., 1998 ), the corresponding bonds differ in length by only 0.022 (2) Å. The other C—N bond lengths within this ring are typical of their types (Allen et al., 1987 ) in both (II) and (III), and the dimensions thus suggest that there is some contribution from the polarized form, (IIIa), in both (II) and (III).

The molecules of (I) are linked into C(6) chains (Bernstein et al., 1995 ) by a single, almost linear, N—H⋯O hydrogen bond (Table 2). Amine atom N7 in the molecule at (x, y, z) acts as donor to carbonyl atom O4 in the molecule at (x − 1, $[{3 \over 2}]$ − y, z − $[{1 \over 2}]$ ), so forming a chain running parallel to the [201] direction and generated by the c-glide plane at y = $[{3 \over 4}]$ (Fig. 3). Two such chains, which are related to one another by inversion and hence antiparallel to each other, pass through each unit cell, but there are no direction-specific interactions between adjacent chains.

Within the asymmetric unit of compound (II), the independent molecular components are linked by two nearly linear N—H⋯N hydrogen bonds (Table 4), forming an R $[{_2^2}]$ (8) motif. These units are linked into a chain by one two-centre N—H⋯O hydrogen bond and one three-centre N—H⋯(O,N) hydrogen bond. Atom N25 at (x, y, z) acts as hydrogen-bond donor, via atom H25B, to atom N11 at (x − $[{3 \over 2}]$ , $[{3 \over 2}]$ − y, $[{1 \over 2}]$ + z). At the same time, atom N24 at (x, y, z) acts as donor to both atoms O14 and N13 at (x − $[{3 \over 2}]$ , $[{3 \over 2}]$ − y, $[{1 \over 2}]$ + z), forming a markedly asymmetric, but planar, three-centre interaction. Propagation of these hydrogen bonds then forms a complex chain of rings, containing [R $[{_1^2}]$ (5)][R $[{_2^1}]$ (6)][R $[{_2^2}]$ (8)] sequences of three edge-fused rings (Fig. 4). This chain is generated by the c-glide plane at y = $[{3 \over 4}]$ and runs parallel to the [30 $[\overline 1]$ ] direction. Two chains of this type pass through each unit cell, but there are no direction-specific interactions between adjacent chains.

It is pertinent to reconsider the supramolecular structure of the pure triazole component, (III). This was described (Borbulevych et al., 1998) as forming hydrogen-bonded layers parallel to the ab plane. However, analysis of the original atom coordinates using PLATON (Spek, 2003 ) clearly shows that the supramolecular structure consists of a C(4)C(5)[R $[{_2^2}]$ (7)] chain of rings running parallel to the [010] direction (Fig. 5). The formation of this chain utilizes only two of the three available N—H bonds, but there are no plausible acceptors available within hydrogen-bonding range of the third N—H bond, so that the supramolecular structure of (III) is properly described as one-dimensional.

Figure 1
The molecule of (I

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
The independent molecular components of (II

), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 3
Part of the crystal structure of (I

), showing the formation of a chain along [201]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, $[{3 \over 2}]$ − y, z − $[{1 \over 2}]$ ) and (1 + x, $[{3 \over 2}]$ − y, $[{1 \over 2}]$ + z), respectively.

Figure 4
Part of the crystal structure of (II

), showing the formation of a chain of rings along [30 $[\overline 1]$ ]. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − $[{3 \over 2}]$ , $[{3 \over 2}]$ − y, $[{1 \over 2}]$ + z) and ( $[{3 \over 2}]$ + x, $[{3 \over 2}]$ − y, z − $[{1 \over 2}]$ ), respectively.

Figure 5
Part of the crystal structure of (III

) (Borbulevych et al., 1998

), showing the formation of a chain of rings along [010]. The original atomic coordinates and atom-labelling scheme have been used. Atoms marked with an asterisk (*), a hash (#) or a dollar sign ($) are at the symmetry positions (−x, $[{1 \over 2}]$ + y, $[{1 \over 2}]$ − z), (x, 1 + y, z) and (−x, y − $[{1 \over 2}]$ , $[{1 \over 2}]$ − z), respectively.

Experimental

For the preparation of (I) and (II), an equimolar mixture of 3-amino-5-trifluoromethyl-1,2,4-triazole and ethyl acetoacetate (1 mmol of each) in toluene (27 ml) was heated under reflux for 2 h. The mixture was cooled to ambient temperature and the resulting solid was collected. Chromatographic purification (Zohdi, 1997) gave pure (I), and crystals of (I) suitable for single-crystal X-ray diffraction were grown from a solution in ethanol. By contrast, successive recrystallizations of the crude reaction mixture from EtOH and then from Me₂CO–CHCl₃ (1:1 v/v) gave crystals of (II) suitable for single-crystal X-ray diffraction.

Compound (I)

Crystal data

C₇H₅F₃N₄O
M_r = 218.15
Monoclinic, P2₁/c
a = 4.6152 (4) Å
b = 20.504 (2) Å
c = 8.7094 (9) Å
β = 91.378 (7)°
V = 823.93 (14) Å³
Z = 4
D_x = 1.759 Mg m⁻³
Mo Kα radiation
Cell parameters from 1862 reflections
θ = 3.1–27.5°
μ = 0.17 mm⁻¹
T = 120 (2) K
Block, colourless
0.42 × 0.20 × 0.12 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ scans, and ω scans with κ offsets
Absorption correction: multi-scan (DENZO–SMN; Otwinowski & Minor, 1997 ) T_min = 0.922, T_max = 0.980
8410 measured reflections
1862 independent reflections
1288 reflections with I > 2σ(I)
R_int = 0.053
θ_max = 27.5°
h = −5 → 5
k = −26 → 23
l = −11 → 11

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.173
S = 1.02
1862 reflections
138 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.1146P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.53 e Å⁻³
Extinction correction: SHELXL97 (Sheldrick, 1997 )
Extinction coefficient: 0.071 (10)

Table 1
Selected interatomic distances (Å) for (I)

N1—C2	1.362 (3)
C2—N3	1.316 (3)
N3—N3a	1.369 (3)
N3a—C4	1.405 (3)
C4—C5	1.424 (3)
C5—C6	1.361 (3)
C6—N7	1.368 (3)
N7—C7a	1.350 (3)
C7a—N1	1.312 (3)
N3a—C7a	1.363 (3)
C4—O4	1.235 (3)
C2—C21	1.496 (3)

Table 2
Hydrogen-bonding geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O4ⁱ	0.88	1.83	2.713 (2)	179
Symmetry code: (i) $[x-1,{\script{3\over 2}}-y,z-{\script{1\over 2}}]$ .

Compound (II)

Crystal data

C₃H₃F₃N₄·C₇H₅F₃N₄O
M_r = 370.24
Monoclinic, Cc
a = 5.0752 (4) Å
b = 22.182 (2) Å
c = 12.3960 (11) Å
β = 91.3200 (5)°
V = 1395.2 (2) Å³
Z = 4
D_x = 1.763 Mg m⁻³
Mo Kα radiation
Cell parameters from 1596 reflections
θ = 3.3–27.5°
μ = 0.18 mm⁻¹
T = 120 (2) K
Plate, colourless
0.55 × 0.18 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ scans, and ω scans with κ offsets
Absorption correction: multi-scan (SORTAV; Blessing, 1995 , 1997 ) T_min = 0.948, T_max = 0.993
8977 measured reflections
1596 independent reflections
1176 reflections with I > 2σ(I)
R_int = 0.061
θ_max = 27.5°
h = −6 → 6
k = −28 → 28
l = −16 → 16

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.110
S = 1.03
1596 reflections
227 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0677P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 3
Selected interatomic distances (Å) for (II)

N11—C12	1.361 (5)
C12—N13	1.312 (5)
N13—N13a	1.369 (5)
N13a—C14	1.404 (5)
C14—C15	1.417 (6)
C15—C16	1.372 (6)
C16—N17	1.364 (5)
N17—C17a	1.351 (5)
C17a—N11	1.323 (5)
N13a—C17a	1.355 (5)
C14—O14	1.235 (5)
C12—C121	1.498 (6)
C22—C221	1.488 (6)
N21—C22	1.363 (5)
C22—N23	1.298 (5)
N23—N24	1.358 (5)
N24—C25	1.356 (5)
C25—N21	1.329 (5)
C25—N25	1.342 (5)

Table 4
Hydrogen-bonding geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N17—H17⋯N21	0.88	2.00	2.868 (4)	168
N25—H25A⋯N11	0.88	2.12	2.987 (5)	167
N24—H24⋯N13ⁱ	0.88	2.41	3.193 (4)	149
N24—H24⋯O14ⁱ	0.88	2.16	2.860 (5)	136
N25—H25B⋯O14ⁱ	0.88	2.10	2.853 (4)	143
Symmetry codes: (i) $[x-{\script{3\over 2}},{\script{3\over 2}}-y,{\script{1\over 2}}+z]$ .

For compound (I), the space group P2₁/c was uniquely assigned from the systematic absences. Crystals of (II) are monoclinic and the systematic absences permitted Cc and C2/c as possible space groups. Consideration of the unit-cell volume suggested space group Cc, and this was confirmed by the subsequent structure analysis. All H atoms were located from difference maps and then treated as riding atoms, with C—H distances of 0.95 (ring CH) or 0.98 Å (CH₃) and N—H distances of 0.88 Å, and with U_iso(H) = 1.2U_eq(C,N), or 1.5U_eq(C) for the methyl group. In the absence of any significant anomalous scattering, the Flack (1983 ) parameter was indeterminate (Flack & Bernardinelli, 2000 ) and it was not possible to establish the correct orientation of the structure of (II) relative to the polar-axis directions (Jones, 1986 ). Accordingly, the Friedel-equivalent reflections were merged prior to the final refinements. However, although the data are 99.2% complete to θ = 27.47°, with merged equivalents the ratio of data to parameters is rather low at only 7.0.

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997 ); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN. For compound (I), program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). For compound (II), program(s) used to solve structure: OSCAIL (McArdle, 2003 ) and SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: OSCAIL and SHELXL97 (Sheldrick, 1997). For both compounds, molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I, II. DOI: 10.1107/S0108270104020256/sk1761sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104020256/sk1761Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270104020256/sk1761IIsup3.hkl

Comment top

In the course of our studies of fluorinated triazole precursors of potential anti-malarial compounds, we needed to prepare 3-methyl-5-(trifluoromethyl)-[1,2,4]triazolo[1,5-a]pyrimidin-7-one, (I). The preparation of this compound by the reaction of 3-amino-5-trifluoromethyl-1H-1,2,4-triazole with ethyl acetoacetate has recently been reported (Zohdi, 1997), and use of the reported chromatographic purification readily affords pure (I). However, we have found that, when purification of the crude reaction product is attempted using recrystallization methods, the crystalline material obtained is not the expected triazolopyrimidinone, (I), but a co-crystal, (II), containing a 1:1 molar ratio of (I) with the starting triazole. Here, we report the molecular and supramolecular structures of both (I) and the co-crystal, (II). \sch

Within the triazole component of (II), the N21—C25 and N25—C25 bonds are too similar in length to be convincingly represented as double and single bonds, respectively. In pure 3-amino-5-trifluoromethyl-1H-1,2,4-triazole itself, (III) (Borbulevych et al., 1998), the corresponding bonds differ in length by only 0.022 (2) Å. The other C—N bond lengths within this ring are typical of their types (Allen et al., 1987) in both (II) and (III), and the dimensions thus suggest that there is some contribution from the polarized form, (IIIa), in both (II) and (III).

The molecules of (I) are linked into C(6) chains (Bernstein et al., 1995) by a single, almost linear, N—H···O hydrogen bond (Table 2). Amino atom N7 in the molecule at (x, y, z) acts as donor to carbonyl atom O4 in the molecule at (x − 1, 3/2 − y, z − 1/2), so forming a chain running parallel to the [201] direction and generated by the c-glide plane at y = 3/4 (Fig. 3). Two such chains, which are related to one another by inversion and are hence anti-parallel to each other, pass through each unit cell, but there are no direction-specific interactions between adjacent chains.

Within the asymmetric unit of compound (II), the independent molecular components are linked by two nearly linear N—H···N hydrogen bonds (Table 4), forming an R₂²(8) motif. These units are linked into a chain by one two-centre N—H···O hydrogen bond and one three-centre N—H···(O,N) hydrogen bond. Atom N25 at (x, y, z) acts as hydrogen-bond donor, via atom H25B, to atom N11 at (x − 3/2, 3/2 − y, 1/2 + z). At the same time, atom N24 at (x, y, z) acts as donor to both atoms O14 and N13 at (x − 3/2, 3/2 − y, 1/2 + z), forming a markedly asymmetric, but planar, three-centre interaction. Propagation of these hydrogen bonds then forms a complex chain of rings, containing [R₁²(5)][R₂¹(6)][R₂²(8)] sequences of three edge-fused rings (Fig. 4). This chain is generated by the c-glide plane at y = 3/4 and it runs parallel to the [301] direction. Two chains of this type pass through each unit cell, but there are no direction-specific interactions between adjacent chains.

It is pertinent to reconsider the supramolecular structure of the pure triazole component, (III). This was described (Borbulevych et al., 1998) as forming hydrogen-bonded layers parallel to the ab plane. However, analysis of the original atom coordinates using PLATON (Spek, 2003) clearly shows that the supramolecular structure consists of a C(4) C(5)[R₂²(7)] chain of rings running parallel to the [010] direction (Fig. 5). The formation of this chain utilizes only two of the three available N—H bonds, but there are no plausible acceptors available within hydrogen-bonding range of the third N—H bond, so that the supramolecular structure of (III) is properly described as one-dimensional.

Experimental top

For the preparation of (I) and (II), an equimolar mixture of 3-amino-5-trifluoromethyl-1,2,4-triazole and ethyl acetoacetate (1 mmol of each) in toluene (27 ml) was heated under reflux for 2 h. The mixture was cooled to ambient temperature and the resulting solid was collected. Chromatographic purification (Zohdi, 1997) gave pure (I), and crystals of (I) suitable for single-crystal X-ray diffraction were grown from a solution in ethanol. By contrast, successive recrystallizations of the crude reaction mixture from EtOH and then from Me₂CO/CHCl₃ (1/1, v/v) gave crystals of (II) suitable for single-crystal X-ray diffraction.

Computing details top

For both compounds, data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for (I); OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997) for (II). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I); OSCAIL and SHELXL97 (Sheldrick, 1997) for (II). For both compounds, molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. The molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The independent molecular components of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. Part of the crystal structure of (I), showing formation of a chain along [201]. For the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 1, 3/2 − y, z − 1/2) and (1 + x, 3/2 − y, 1/2 + z), respectively.
	Fig. 4. Part of the crystal structure of (II), showing formation of a chain of rings along [301]. For the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*) or a hash (#) are at the symmetry positions (x − 3/2, 3/2 − y, 1/2 + z) and (3/2 + x, 3/2 − y, z − 1/2), respectively.
	Fig. 5. Part of the crystal structure of (III) (Borbulevych et al., 1998), showing formation of a chain of rings along [010]. The original atomic coordinates and atom-labelling scheme have been used. The atoms marked with an asterisk (*), a hash (#) or a dollar sign () are at the symmetry positions (-x, 1/2 + y, 1/2 − z), (x, 1 + y, z) and (-x, y − 1/2, 1/2 − z), respectively.

(I) 5-methyl-2-trifluoromethyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one top

Crystal data top

C₇H₅F₃N₄O	F(000) = 440
M_r = 218.15	D_x = 1.759 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1862 reflections
a = 4.6152 (4) Å	θ = 3.1–27.5°
b = 20.504 (2) Å	µ = 0.17 mm⁻¹
c = 8.7094 (9) Å	T = 120 K
β = 91.378 (7)°	Block, colourless
V = 823.93 (14) Å³	0.42 × 0.20 × 0.12 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	1862 independent reflections
Radiation source: fine-focus sealed X-ray tube	1288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	h = −5→5
T_min = 0.922, T_max = 0.980	k = −26→23
8410 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.065	H-atom parameters constrained
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.1146P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
1862 reflections	Δρ_max = 0.65 e Å⁻³
138 parameters	Δρ_min = −0.53 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.071 (10)

Crystal data top

C₇H₅F₃N₄O	V = 823.93 (14) Å³
M_r = 218.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.6152 (4) Å	µ = 0.17 mm⁻¹
b = 20.504 (2) Å	T = 120 K
c = 8.7094 (9) Å	0.42 × 0.20 × 0.12 mm
β = 91.378 (7)°

Data collection top

Nonius KappaCCD area-detector diffractometer	1862 independent reflections
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	1288 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.980	R_int = 0.053
8410 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.02	Δρ_max = 0.65 e Å⁻³
1862 reflections	Δρ_min = −0.53 e Å⁻³
138 parameters

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

	x	y	z	U_iso*/U_eq
F21	−0.1721 (3)	0.52415 (8)	0.2457 (2)	0.0537 (6)
F22	0.2289 (3)	0.51437 (7)	0.13118 (15)	0.0386 (5)
F23	0.2028 (4)	0.48649 (7)	0.36639 (17)	0.0475 (5)
O4	0.7878 (3)	0.68786 (8)	0.58691 (17)	0.0290 (5)
N1	0.0722 (4)	0.65130 (9)	0.2409 (2)	0.0247 (5)
N3	0.4013 (4)	0.60891 (9)	0.4147 (2)	0.0249 (5)
N3a	0.4146 (4)	0.67558 (9)	0.4130 (2)	0.0233 (5)
N7	0.1892 (4)	0.76402 (9)	0.2895 (2)	0.0239 (5)
C2	0.1948 (5)	0.59834 (11)	0.3109 (3)	0.0255 (6)
C4	0.6088 (5)	0.71441 (12)	0.4997 (2)	0.0244 (5)
C5	0.5643 (5)	0.78230 (11)	0.4739 (2)	0.0242 (5)
C6	0.3613 (5)	0.80605 (11)	0.3727 (2)	0.0247 (5)
C7a	0.2155 (4)	0.69892 (11)	0.3087 (2)	0.0222 (5)
C21	0.1123 (5)	0.53028 (12)	0.2658 (3)	0.0301 (6)
C61	0.3113 (5)	0.87660 (12)	0.3425 (3)	0.0306 (6)
H5	0.6820	0.8124	0.5300	0.029*
H6A	0.1061	0.8868	0.3561	0.046*
H6B	0.3649	0.8869	0.2371	0.046*
H6C	0.4300	0.9026	0.4146	0.046*
H7	0.0605	0.7795	0.2229	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F21	0.0276 (9)	0.0371 (10)	0.0961 (14)	−0.0050 (7)	−0.0038 (8)	−0.0253 (9)
F22	0.0494 (9)	0.0331 (9)	0.0331 (8)	−0.0012 (6)	−0.0005 (6)	−0.0083 (6)
F23	0.0754 (12)	0.0266 (9)	0.0397 (9)	−0.0040 (7)	−0.0118 (8)	0.0054 (7)
O4	0.0284 (9)	0.0300 (10)	0.0279 (9)	0.0020 (7)	−0.0113 (7)	−0.0010 (7)
N1	0.0251 (10)	0.0243 (11)	0.0244 (10)	0.0000 (8)	−0.0052 (7)	−0.0026 (8)
N3	0.0270 (10)	0.0190 (11)	0.0283 (10)	0.0004 (8)	−0.0042 (8)	−0.0015 (8)
N3a	0.0240 (10)	0.0216 (11)	0.0240 (10)	0.0005 (8)	−0.0047 (7)	−0.0017 (8)
N7	0.0247 (10)	0.0234 (11)	0.0233 (10)	0.0027 (8)	−0.0065 (7)	0.0021 (8)
C2	0.0255 (12)	0.0259 (13)	0.0248 (11)	−0.0009 (9)	−0.0025 (9)	−0.0003 (9)
C4	0.0223 (11)	0.0279 (13)	0.0229 (11)	−0.0002 (9)	−0.0010 (8)	−0.0026 (9)
C5	0.0250 (11)	0.0242 (12)	0.0233 (11)	−0.0021 (9)	−0.0029 (8)	−0.0028 (9)
C6	0.0268 (12)	0.0250 (13)	0.0222 (12)	−0.0024 (9)	0.0013 (8)	−0.0041 (9)
C7a	0.0209 (11)	0.0243 (13)	0.0212 (11)	0.0013 (9)	−0.0019 (8)	0.0003 (9)
C21	0.0298 (13)	0.0271 (13)	0.0331 (13)	−0.0007 (10)	−0.0034 (9)	−0.0019 (10)
C61	0.0347 (13)	0.0235 (13)	0.0333 (14)	0.0018 (11)	−0.0041 (10)	−0.0018 (10)

Geometric parameters (Å, º) top

N1—C2	1.362 (3)	C2—C21	1.496 (3)
C2—N3	1.316 (3)	F21—C21	1.326 (3)
N3—N3a	1.369 (3)	F22—C21	1.342 (3)
N3a—C4	1.405 (3)	F23—C21	1.315 (3)
C4—C5	1.424 (3)	C5—H5	0.95
C5—C6	1.361 (3)	C6—C61	1.487 (3)
C6—N7	1.368 (3)	C61—H6A	0.98
N7—C7a	1.350 (3)	C61—H6B	0.98
C7a—N1	1.312 (3)	C61—H6C	0.98
N3a—C7a	1.363 (3)	N7—H7	0.88
C4—O4	1.235 (3)

C7a—N1—C2	101.12 (18)	C6—C5—H5	118.4
N3—C2—N1	117.5 (2)	C4—C5—H5	118.4
N3—C2—C21	120.6 (2)	C5—C6—N7	120.0 (2)
N1—C2—C21	121.7 (2)	C5—C6—C61	124.3 (2)
F23—C21—F21	108.7 (2)	N7—C6—C61	115.7 (2)
F23—C21—F22	106.76 (19)	C6—C61—H6A	109.5
F21—C21—F22	106.16 (18)	C6—C61—H6B	109.5
F23—C21—C2	112.78 (19)	H6A—C61—H6B	109.5
F21—C21—C2	111.57 (19)	C6—C61—H6C	109.5
F22—C21—C2	110.55 (19)	H6A—C61—H6C	109.5
C2—N3—N3a	100.91 (17)	H6B—C61—H6C	109.5
C7a—N3a—N3	109.13 (17)	C7a—N7—C6	120.52 (18)
C7a—N3a—C4	124.77 (19)	C7a—N7—H7	119.7
N3—N3a—C4	126.06 (17)	C6—N7—H7	119.7
O4—C4—N3a	119.3 (2)	N1—C7a—N7	129.59 (19)
O4—C4—C5	128.3 (2)	N1—C7a—N3a	111.29 (19)
N3a—C4—C5	112.42 (18)	N7—C7a—N3a	119.11 (19)
C6—C5—C4	123.1 (2)

C7a—N1—C2—N3	−0.4 (3)	N3—N3a—C4—C5	−179.10 (19)
C7a—N1—C2—C21	−176.8 (2)	O4—C4—C5—C6	179.1 (2)
N3—C2—C21—F23	17.8 (3)	N3a—C4—C5—C6	−1.8 (3)
N1—C2—C21—F23	−165.9 (2)	C4—C5—C6—N7	−0.4 (3)
N3—C2—C21—F21	140.5 (2)	C4—C5—C6—C61	−179.6 (2)
N1—C2—C21—F21	−43.2 (3)	C5—C6—N7—C7a	1.2 (3)
N3—C2—C21—F22	−101.6 (2)	C61—C6—N7—C7a	−179.57 (19)
N1—C2—C21—F22	74.7 (3)	C2—N1—C7a—N7	−179.1 (2)
N1—C2—N3—N3a	0.3 (2)	C2—N1—C7a—N3a	0.4 (2)
C21—C2—N3—N3a	176.70 (19)	C6—N7—C7a—N1	179.9 (2)
C2—N3—N3a—C7a	0.0 (2)	C6—N7—C7a—N3a	0.4 (3)
C2—N3—N3a—C4	−177.7 (2)	N3—N3a—C7a—N1	−0.2 (2)
C7a—N3a—C4—O4	−177.25 (19)	C4—N3a—C7a—N1	177.46 (18)
N3—N3a—C4—O4	0.1 (3)	N3—N3a—C7a—N7	179.27 (18)
C7a—N3a—C4—C5	3.6 (3)	C4—N3a—C7a—N7	−3.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O4ⁱ	0.88	1.83	2.713 (2)	179

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

(II) 3-amino-5-trifluoromethyl-1H-1,2,4-triazole– 5-methyl-2-trifluoromethyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one (1/1) top

Crystal data top

C₃H₃F₃N₄·C₇H₅F₃N₄O	F(000) = 744
M_r = 370.24	D_x = 1.763 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1596 reflections
a = 5.0752 (4) Å	θ = 3.3–27.5°
b = 22.182 (2) Å	µ = 0.18 mm⁻¹
c = 12.3960 (11) Å	T = 120 K
β = 91.3200 (5)°	Plate, colourless
V = 1395.2 (2) Å³	0.55 × 0.18 × 0.04 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	1596 independent reflections
Radiation source: rotating anode	1176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ scans, and ω scans with κ offsets	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −6→6
T_min = 0.948, T_max = 0.993	k = −28→28
8977 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0677P)²] where P = (F_o² + 2F_c²)/3
1596 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.25 e Å⁻³
2 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₃H₃F₃N₄·C₇H₅F₃N₄O	V = 1395.2 (2) Å³
M_r = 370.24	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 5.0752 (4) Å	µ = 0.18 mm⁻¹
b = 22.182 (2) Å	T = 120 K
c = 12.3960 (11) Å	0.55 × 0.18 × 0.04 mm
β = 91.3200 (5)°

Data collection top

Nonius KappaCCD area-detector diffractometer	1596 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	1176 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.993	R_int = 0.061
8977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	2 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
1596 reflections	Δρ_min = −0.28 e Å⁻³
227 parameters

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

	x	y	z	U_iso*/U_eq
F121	0.2594 (6)	0.88968 (12)	0.5318 (3)	0.0574 (8)
F122	0.6378 (6)	0.88378 (12)	0.6120 (2)	0.0520 (7)
F123	0.6108 (5)	0.91107 (11)	0.4469 (2)	0.0449 (7)
O14	0.9903 (5)	0.70589 (13)	0.3008 (2)	0.0342 (7)
N11	0.3680 (6)	0.76650 (15)	0.5263 (3)	0.0277 (8)
N13	0.7101 (6)	0.79148 (14)	0.4179 (2)	0.0267 (7)
N13a	0.6641 (6)	0.73067 (14)	0.4156 (2)	0.0258 (7)
N17	0.3804 (6)	0.65950 (15)	0.4898 (2)	0.0278 (7)
C12	0.5292 (8)	0.80928 (19)	0.4848 (3)	0.0280 (9)
C14	0.7995 (8)	0.68870 (19)	0.3527 (3)	0.0283 (9)
C15	0.6937 (8)	0.62978 (19)	0.3606 (3)	0.0302 (9)
C16	0.4914 (8)	0.61592 (18)	0.4278 (3)	0.0291 (9)
C17a	0.4606 (7)	0.71726 (18)	0.4803 (3)	0.0261 (8)
C121	0.5084 (8)	0.8741 (2)	0.5176 (3)	0.0342 (10)
C161	0.3770 (9)	0.55411 (18)	0.4364 (4)	0.0382 (10)
F221	0.1869 (5)	0.52602 (13)	0.6966 (2)	0.0516 (7)
F222	−0.2027 (7)	0.49841 (13)	0.7390 (3)	0.0755 (12)
F223	−0.1152 (5)	0.51899 (11)	0.5748 (2)	0.0479 (7)
N21	−0.0183 (6)	0.64663 (14)	0.6485 (3)	0.0285 (8)
N23	−0.3334 (7)	0.61325 (16)	0.7604 (3)	0.0341 (9)
N24	−0.3346 (6)	0.67441 (16)	0.7552 (3)	0.0300 (8)
N25	−0.0922 (7)	0.75220 (15)	0.6700 (3)	0.0298 (7)
C22	−0.1431 (8)	0.59970 (18)	0.6965 (3)	0.0312 (9)
C25	−0.1428 (7)	0.69385 (17)	0.6893 (3)	0.0266 (9)
C221	−0.0683 (9)	0.5357 (2)	0.6779 (4)	0.0399 (10)
H15	0.7657	0.5987	0.3177	0.036*
H16A	0.3863	0.5409	0.5118	0.057*
H16B	0.4770	0.5262	0.3919	0.057*
H16C	0.1926	0.5548	0.4112	0.057*
H17	0.2574	0.6500	0.5357	0.033*
H24	−0.4440	0.6980	0.7896	0.036*
H25A	0.0348	0.7623	0.6264	0.036*
H25B	−0.1861	0.7804	0.7011	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F121	0.0476 (16)	0.0366 (15)	0.089 (2)	0.0044 (11)	0.0172 (15)	−0.0123 (14)
F122	0.086 (2)	0.0376 (16)	0.0325 (14)	−0.0062 (13)	−0.0058 (13)	−0.0074 (11)
F123	0.0647 (18)	0.0315 (14)	0.0390 (14)	−0.0053 (12)	0.0091 (13)	0.0046 (11)
O14	0.0370 (16)	0.0400 (17)	0.0260 (14)	−0.0003 (14)	0.0103 (13)	0.0013 (12)
N11	0.0297 (18)	0.0292 (19)	0.0243 (16)	−0.0003 (13)	0.0019 (14)	−0.0016 (13)
N13	0.0300 (17)	0.0299 (19)	0.0205 (16)	0.0004 (13)	0.0035 (14)	0.0005 (13)
N13a	0.0304 (17)	0.0298 (18)	0.0176 (14)	−0.0007 (14)	0.0058 (13)	0.0002 (13)
N17	0.0309 (17)	0.0290 (18)	0.0237 (16)	0.0002 (13)	0.0032 (14)	0.0002 (13)
C12	0.031 (2)	0.031 (2)	0.023 (2)	0.0002 (17)	0.0030 (17)	0.0022 (16)
C14	0.029 (2)	0.038 (2)	0.0186 (17)	0.0016 (17)	0.0019 (16)	0.0001 (16)
C15	0.032 (2)	0.035 (2)	0.0243 (19)	0.0020 (17)	0.0048 (17)	−0.0033 (16)
C16	0.030 (2)	0.032 (2)	0.025 (2)	0.0026 (17)	−0.0012 (18)	−0.0032 (16)
C17a	0.0236 (19)	0.035 (2)	0.0192 (18)	−0.0043 (16)	−0.0004 (15)	0.0003 (16)
C121	0.037 (2)	0.037 (2)	0.029 (2)	−0.0009 (18)	0.0064 (18)	−0.0017 (19)
C161	0.045 (2)	0.034 (2)	0.036 (2)	−0.0023 (19)	0.006 (2)	−0.0029 (19)
F221	0.0519 (17)	0.0494 (17)	0.0531 (16)	0.0185 (13)	−0.0041 (13)	−0.0009 (13)
F222	0.096 (3)	0.0348 (16)	0.099 (3)	0.0066 (16)	0.062 (2)	0.0194 (16)
F223	0.0526 (16)	0.0369 (13)	0.0540 (17)	−0.0002 (11)	0.0000 (13)	−0.0112 (13)
N21	0.0286 (19)	0.0307 (19)	0.0265 (17)	0.0007 (14)	0.0041 (14)	0.0026 (14)
N23	0.037 (2)	0.033 (2)	0.033 (2)	0.0008 (14)	0.0093 (17)	0.0044 (14)
N24	0.0311 (19)	0.032 (2)	0.0274 (17)	0.0023 (14)	0.0076 (15)	−0.0001 (14)
N25	0.0312 (17)	0.0286 (18)	0.0298 (17)	0.0023 (14)	0.0078 (14)	0.0009 (14)
C22	0.034 (2)	0.034 (2)	0.0260 (19)	0.0005 (18)	0.0022 (18)	0.0041 (18)
C25	0.028 (2)	0.032 (2)	0.0196 (18)	0.0018 (17)	−0.0038 (16)	0.0013 (17)
C221	0.047 (3)	0.033 (2)	0.040 (2)	0.0016 (19)	0.015 (2)	0.0079 (19)

Geometric parameters (Å, º) top

N11—C12	1.361 (5)	C161—H16A	0.98
C12—N13	1.312 (5)	C161—H16B	0.98
N13—N13a	1.369 (5)	C161—H16C	0.98
N13a—C14	1.404 (5)	N17—H17	0.88
C14—C15	1.417 (6)	C22—C221	1.488 (6)
C15—C16	1.372 (6)	N21—C22	1.363 (5)
C16—N17	1.364 (5)	C22—N23	1.298 (5)
N17—C17a	1.351 (5)	N23—N24	1.358 (5)
C17a—N11	1.323 (5)	N24—C25	1.356 (5)
N13a—C17a	1.355 (5)	C25—N21	1.329 (5)
C14—O14	1.235 (5)	C25—N25	1.342 (5)
C12—C121	1.498 (6)	C221—F222	1.322 (5)
C121—F123	1.316 (5)	C221—F221	1.328 (6)
C121—F121	1.326 (5)	C221—F223	1.347 (5)
C121—F122	1.346 (5)	N24—H24	0.88
C15—H15	0.95	N25—H25A	0.88
C16—C161	1.494 (6)	N25—H25B	0.88

C17a—N11—C12	100.9 (3)	H16B—C161—H16C	109.5
N13—C12—N11	117.7 (4)	C17a—N17—C16	119.6 (3)
N13—C12—C121	121.0 (4)	C17a—N17—H17	120.2
N11—C12—C121	121.3 (3)	C16—N17—H17	120.2
F123—C121—F121	108.5 (4)	N11—C17a—N17	129.4 (4)
F123—C121—F122	106.7 (4)	N11—C17a—N13a	110.9 (4)
F121—C121—F122	106.8 (3)	N17—C17a—N13a	119.7 (3)
F123—C121—C12	112.8 (3)	C25—N21—C22	101.9 (3)
F121—C121—C12	111.1 (4)	N23—C22—N21	116.7 (4)
F122—C121—C12	110.7 (3)	N23—C22—C221	120.8 (4)
C12—N13—N13a	100.9 (3)	N21—C22—C221	122.5 (4)
C17a—N13a—N13	109.6 (3)	F222—C221—F221	108.2 (4)
C17a—N13a—C14	124.9 (3)	F222—C221—F223	106.8 (4)
N13—N13a—C14	125.4 (3)	F221—C221—F223	105.7 (3)
O14—C14—N13a	119.0 (4)	F222—C221—C22	111.8 (4)
O14—C14—C15	128.6 (4)	F221—C221—C22	112.3 (4)
N13a—C14—C15	112.4 (3)	F223—C221—C22	111.7 (4)
C16—C15—C14	122.6 (4)	C22—N23—N24	101.8 (3)
C16—C15—H15	118.7	C25—N24—N23	110.1 (3)
C14—C15—H15	118.7	C25—N24—H24	125.0
N17—C16—C15	120.5 (4)	N23—N24—H24	125.0
N17—C16—C161	116.4 (4)	N21—C25—N25	126.7 (4)
C15—C16—C161	123.1 (4)	N21—C25—N24	109.5 (3)
C16—C161—H16A	109.5	N25—C25—N24	123.8 (3)
C16—C161—H16B	109.5	C25—N25—H25A	120.0
H16A—C161—H16B	109.5	C25—N25—H25B	120.0
C16—C161—H16C	109.5	H25A—N25—H25B	120.0
H16A—C161—H16C	109.5

C17a—N11—C12—N13	0.3 (4)	C12—N11—C17a—N13a	−0.1 (4)
C17a—N11—C12—C121	−177.4 (4)	C16—N17—C17a—N11	174.8 (4)
N13—C12—C121—F123	23.6 (6)	C16—N17—C17a—N13a	−5.1 (5)
N11—C12—C121—F123	−158.9 (3)	N13—N13a—C17a—N11	−0.1 (4)
N13—C12—C121—F121	145.7 (4)	C14—N13a—C17a—N11	−177.9 (3)
N11—C12—C121—F121	−36.8 (5)	N13—N13a—C17a—N17	179.7 (3)
N13—C12—C121—F122	−95.8 (4)	C14—N13a—C17a—N17	2.0 (5)
N11—C12—C121—F122	81.7 (5)	C25—N21—C22—N23	1.3 (5)
N11—C12—N13—N13a	−0.3 (4)	C25—N21—C22—C221	−178.6 (4)
C121—C12—N13—N13a	177.3 (3)	N23—C22—C221—F222	−4.7 (6)
C12—N13—N13a—C17a	0.3 (4)	N21—C22—C221—F222	175.3 (4)
C12—N13—N13a—C14	178.0 (3)	N23—C22—C221—F221	−126.5 (4)
C17a—N13a—C14—O14	−176.6 (3)	N21—C22—C221—F221	53.4 (5)
N13—N13a—C14—O14	6.0 (5)	N23—C22—C221—F223	114.9 (4)
C17a—N13a—C14—C15	2.2 (5)	N21—C22—C221—F223	−65.2 (6)
N13—N13a—C14—C15	−175.1 (3)	N21—C22—N23—N24	−0.4 (5)
O14—C14—C15—C16	175.1 (4)	C221—C22—N23—N24	179.5 (4)
N13a—C14—C15—C16	−3.6 (5)	C22—N23—N24—C25	−0.7 (4)
C14—C15—C16—N17	0.8 (6)	C22—N21—C25—N25	178.4 (4)
C14—C15—C16—C161	179.6 (4)	C22—N21—C25—N24	−1.6 (4)
C15—C16—N17—C17a	3.7 (6)	N23—N24—C25—N21	1.5 (4)
C161—C16—N17—C17a	−175.2 (3)	N23—N24—C25—N25	−178.5 (4)
C12—N11—C17a—N17	−179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N21	0.88	2.00	2.868 (4)	168
N25—H25A···N11	0.88	2.12	2.987 (5)	167
N24—H24···N13ⁱ	0.88	2.41	3.193 (4)	149
N24—H24···O14ⁱ	0.88	2.16	2.860 (5)	136
N25—H25B···O14ⁱ	0.88	2.10	2.853 (4)	143

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

Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₇H₅F₃N₄O	C₃H₃F₃N₄·C₇H₅F₃N₄O
M_r	218.15	370.24
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, Cc
Temperature (K)	120	120
a, b, c (Å)	4.6152 (4), 20.504 (2), 8.7094 (9)	5.0752 (4), 22.182 (2), 12.3960 (11)
β (°)	91.378 (7)	91.3200 (5)
V (Å³)	823.93 (14)	1395.2 (2)
Z	4	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.17	0.18
Crystal size (mm)	0.42 × 0.20 × 0.12	0.55 × 0.18 × 0.04

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997)	Multi-scan (SORTAV; Blessing, 1995, 1997)
T_min, T_max	0.922, 0.980	0.948, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	8410, 1862, 1288	8977, 1596, 1176
R_int	0.053	0.061
(sin θ/λ)_max (Å⁻¹)	0.649	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.173, 1.02	0.046, 0.110, 1.03
No. of reflections	1862	1596
No. of parameters	138	227
No. of restraints	0	2
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.53	0.25, −0.28

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, OSCAIL (McArdle, 2003) and SHELXS97 (Sheldrick, 1997), OSCAIL and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond lengths (Å) for (I) top

N1—C2	1.362 (3)	C6—N7	1.368 (3)
C2—N3	1.316 (3)	N7—C7a	1.350 (3)
N3—N3a	1.369 (3)	C7a—N1	1.312 (3)
N3a—C4	1.405 (3)	N3a—C7a	1.363 (3)
C4—C5	1.424 (3)	C4—O4	1.235 (3)
C5—C6	1.361 (3)	C2—C21	1.496 (3)

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O4ⁱ	0.88	1.83	2.713 (2)	179

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

Selected bond lengths (Å) for (II) top

N11—C12	1.361 (5)	C14—O14	1.235 (5)
C12—N13	1.312 (5)	C12—C121	1.498 (6)
N13—N13a	1.369 (5)	C22—C221	1.488 (6)
N13a—C14	1.404 (5)	N21—C22	1.363 (5)
C14—C15	1.417 (6)	C22—N23	1.298 (5)
C15—C16	1.372 (6)	N23—N24	1.358 (5)
C16—N17	1.364 (5)	N24—C25	1.356 (5)
N17—C17a	1.351 (5)	C25—N21	1.329 (5)
C17a—N11	1.323 (5)	C25—N25	1.342 (5)
N13a—C17a	1.355 (5)

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
N17—H17···N21	0.88	2.00	2.868 (4)	168
N25—H25A···N11	0.88	2.12	2.987 (5)	167
N24—H24···N13ⁱ	0.88	2.41	3.193 (4)	149
N24—H24···O14ⁱ	0.88	2.16	2.860 (5)	136
N25—H25B···O14ⁱ	0.88	2.10	2.853 (4)	143

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

Footnotes

‡Postal address: School of Engineering, University of Dundee, Dundee DD1 4HN, Scotland.

Acknowledgements

The X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England; the authors thank the staff for all their help and advice. JNL thanks NCR Self-Service, Dundee, for grants which have provided computing facilities for this work. NB, KDBD and SMSVW thank CNPq for financial support.

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Volume 60| Part 10| October 2004| Pages o733-o736

doi:10.1107/S0108270104020256