Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogen-bonding sites

The antifungal drug 5-fluorocytosine (4-amino-5-fluoro-1,2-dihydropyrimidin-2-one) was cocrystallized with five complementary compounds in order to better understand its drug-receptor interaction. The first two compounds, 2-aminopyrimidine (2-amino-1,3-diazine) and N-acetylcreatinine (N-acetyl-2-amino-1-methyl-5H-imidazol-4-one), exhibit donor-acceptor sites for R₂²(8) heterodimer formation with 5-fluorocytosine. Such a heterodimer is observed in the cocrystal with 2-aminopyrimidine (I); in contrast, 5-fluorocytosine and N-acetylcreatinine [which forms homodimers in its crystal structure (II)] are connected only by a single hydrogen bond in (III). The other three compounds 6-aminouracil (6-amino-2,4-pyrimidinediol), 6-aminoisocytosine (2,6-diamino-3H-pyrimidin-4-one) and acyclovir [acycloguanosine or 2-amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one] possess donor-donor-acceptor sites; therefore, they can interact with 5-fluorocytosine to form a heterodimer linked by three hydrogen bonds. In the cocrystals with 6-aminoisocytosine (Va)-(Vd), as well as in the cocrystal with the antiviral drug acyclovir (VII), the desired heterodimers are observed. However, they are not formed in the cocrystal with 6-aminouracil (IV), where the components are connected by two hydrogen bonds. In addition, a solvent-free structure of acyclovir (VI) was obtained. A comparison of the calculated energies released during dimer formation helped to rationalize the preference for hydrogen-bonding interactions in the various cocrystal structures.

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); for (I), (II), (Va), (Vb), (Vc), (Vd), (VII); Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008) for (III), (IV), (VI).

(I) ;

Crystal data

C4H4FN3O·C4H5N3	Z = 2
Mr = 224.21	F(000) = 232
Triclinic, P1	Dx = 1.520 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2414 (12) Å	Cell parameters from 2478 reflections
b = 7.2335 (17) Å	θ = 3.5–25.7°
c = 11.546 (2) Å	µ = 0.12 mm^−1
α = 105.371 (18)°	T = 173 K
β = 101.944 (16)°	Block, colourless
γ = 91.700 (18)°	0.40 × 0.10 × 0.10 mm
V = 489.76 (17) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	1246 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 = −7→7
4298 measured reflections	k = −8→8
1834 independent reflections	l = −13→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)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.210	w = 1/[σ^2(Fo^2) + (0.1395P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
1834 reflections	Δρmax = 0.32 e Å^−3
161 parameters	Δρmin = −0.38 e Å^−3
4 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: 0.058 (18)

Special details

Experimental. ;

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	0.4815 (4)	0.2617 (4)	0.2068 (2)	0.0321 (6)
C2	0.5522 (5)	0.2809 (4)	0.3289 (3)	0.0314 (7)
N3	0.4311 (4)	0.2225 (4)	0.4006 (2)	0.0324 (6)
C4	0.2262 (4)	0.1446 (5)	0.3452 (3)	0.0336 (7)
H4	0.1374	0.1042	0.3931	0.040*
C5	0.1372 (5)	0.1201 (5)	0.2211 (3)	0.0361 (7)
H5	−0.0085	0.0642	0.1830	0.043*
C6	0.2742 (5)	0.1820 (5)	0.1562 (3)	0.0349 (7)
H6	0.2187	0.1675	0.0709	0.042*
N21	0.7574 (4)	0.3574 (4)	0.3848 (2)	0.0364 (7)
H21A	0.804 (5)	0.391 (5)	0.4667 (18)	0.044*
H21B	0.834 (5)	0.412 (5)	0.345 (3)	0.044*
N1'	0.5718 (4)	0.2739 (4)	0.6578 (2)	0.0296 (6)
H1'	0.537 (6)	0.248 (5)	0.577 (4)	0.036*
C2'	0.7823 (4)	0.3500 (4)	0.7204 (3)	0.0297 (7)
N3'	0.8400 (4)	0.3832 (4)	0.8456 (2)	0.0300 (6)
C4'	0.6961 (4)	0.3299 (4)	0.9056 (3)	0.0289 (7)
C5'	0.4848 (4)	0.2423 (5)	0.8380 (3)	0.0320 (7)
C6'	0.4223 (5)	0.2203 (5)	0.7161 (3)	0.0342 (7)
H6'	0.2777	0.1688	0.6719	0.041*
O21'	0.9153 (3)	0.3898 (3)	0.6602 (2)	0.0383 (6)
N41'	0.7527 (4)	0.3599 (4)	1.0271 (2)	0.0353 (7)
H41A	0.661 (5)	0.320 (5)	1.068 (3)	0.042*
H41B	0.879 (4)	0.428 (5)	1.064 (3)	0.042*
F51'	0.3432 (3)	0.1872 (3)	0.90050 (17)	0.0446 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0289 (12)	0.0360 (14)	0.0332 (13)	0.0014 (10)	0.0096 (10)	0.0107 (11)
C2	0.0301 (14)	0.0324 (16)	0.0353 (16)	0.0072 (11)	0.0133 (12)	0.0105 (13)
N3	0.0247 (11)	0.0412 (15)	0.0326 (13)	0.0005 (10)	0.0091 (9)	0.0103 (11)
C4	0.0255 (13)	0.0433 (18)	0.0325 (15)	−0.0002 (12)	0.0086 (11)	0.0101 (13)
C5	0.0259 (13)	0.0413 (18)	0.0363 (16)	−0.0057 (12)	0.0044 (12)	0.0056 (14)
C6	0.0308 (14)	0.0394 (17)	0.0305 (15)	−0.0020 (12)	0.0036 (12)	0.0059 (13)
N21	0.0220 (11)	0.0533 (17)	0.0353 (14)	−0.0061 (11)	0.0070 (10)	0.0154 (12)
N1'	0.0243 (11)	0.0381 (14)	0.0247 (12)	−0.0029 (10)	0.0014 (9)	0.0095 (11)
C2'	0.0234 (12)	0.0325 (16)	0.0345 (15)	0.0011 (11)	0.0062 (11)	0.0118 (13)
N3'	0.0212 (11)	0.0362 (14)	0.0331 (13)	−0.0013 (9)	0.0040 (9)	0.0124 (11)
C4'	0.0266 (13)	0.0299 (15)	0.0321 (15)	0.0026 (11)	0.0078 (11)	0.0108 (12)
C5'	0.0246 (13)	0.0414 (17)	0.0330 (15)	−0.0018 (12)	0.0099 (11)	0.0129 (13)
C6'	0.0240 (13)	0.0429 (18)	0.0356 (16)	−0.0017 (12)	0.0072 (11)	0.0107 (14)
O21'	0.0300 (10)	0.0516 (14)	0.0380 (12)	−0.0031 (9)	0.0106 (9)	0.0188 (10)
N41'	0.0268 (12)	0.0469 (16)	0.0322 (14)	−0.0056 (11)	0.0054 (10)	0.0130 (12)
F51'	0.0304 (9)	0.0678 (14)	0.0373 (10)	−0.0121 (8)	0.0114 (8)	0.0164 (9)

Geometric parameters (Å, º)

N1—C6	1.346 (4)	N1'—C2'	1.380 (4)
N1—C2	1.356 (4)	N1'—H1'	0.88 (4)
C2—N21	1.338 (4)	C2'—O21'	1.259 (3)
C2—N3	1.364 (4)	C2'—N3'	1.369 (4)
N3—C4	1.338 (4)	N3'—C4'	1.347 (4)
C4—C5	1.387 (4)	C4'—N41'	1.329 (4)
C4—H4	0.9500	C4'—C5'	1.419 (4)
C5—C6	1.383 (4)	C5'—C6'	1.345 (4)
C5—H5	0.9500	C5'—F51'	1.363 (3)
C6—H6	0.9500	C6'—H6'	0.9500
N21—H21A	0.894 (19)	N41'—H41A	0.899 (19)
N21—H21B	0.879 (19)	N41'—H41B	0.879 (19)
N1'—C6'	1.360 (4)
C6—N1—C2	115.8 (2)	C6'—N1'—H1'	119 (2)
N21—C2—N1	118.8 (3)	C2'—N1'—H1'	119 (2)
N21—C2—N3	116.3 (3)	O21'—C2'—N3'	121.8 (2)
N1—C2—N3	124.8 (3)	O21'—C2'—N1'	118.6 (3)
C4—N3—C2	116.6 (3)	N3'—C2'—N1'	119.6 (2)
N3—C4—C5	123.1 (3)	C4'—N3'—C2'	119.8 (2)
N3—C4—H4	118.4	N41'—C4'—N3'	120.0 (3)
C5—C4—H4	118.4	N41'—C4'—C5'	120.7 (2)
C6—C5—C4	115.8 (3)	N3'—C4'—C5'	119.3 (3)
C6—C5—H5	122.1	C6'—C5'—F51'	120.6 (3)
C4—C5—H5	122.1	C6'—C5'—C4'	121.1 (3)
N1—C6—C5	123.8 (3)	F51'—C5'—C4'	118.3 (3)
N1—C6—H6	118.1	C5'—C6'—N1'	118.2 (3)
C5—C6—H6	118.1	C5'—C6'—H6'	120.9
C2—N21—H21A	122 (2)	N1'—C6'—H6'	120.9
C2—N21—H21B	119 (2)	C4'—N41'—H41A	121 (2)
H21A—N21—H21B	116 (3)	C4'—N41'—H41B	116 (3)
C6'—N1'—C2'	121.8 (2)	H41A—N41'—H41B	123 (3)
C6—N1—C2—N21	179.4 (3)	N1'—C2'—N3'—C4'	4.3 (4)
C6—N1—C2—N3	1.4 (4)	C2'—N3'—C4'—N41'	179.2 (3)
N21—C2—N3—C4	−179.6 (3)	C2'—N3'—C4'—C5'	−1.0 (4)
N1—C2—N3—C4	−1.5 (4)	N41'—C4'—C5'—C6'	176.6 (3)
C2—N3—C4—C5	0.8 (4)	N3'—C4'—C5'—C6'	−3.2 (5)
N3—C4—C5—C6	−0.1 (5)	N41'—C4'—C5'—F51'	−1.0 (4)
C2—N1—C6—C5	−0.6 (4)	N3'—C4'—C5'—F51'	179.1 (2)
C4—C5—C6—N1	0.0 (5)	F51'—C5'—C6'—N1'	−178.6 (3)
C6'—N1'—C2'—O21'	177.3 (3)	C4'—C5'—C6'—N1'	3.8 (5)
C6'—N1'—C2'—N3'	−3.7 (4)	C2'—N1'—C6'—C5'	−0.4 (4)
O21'—C2'—N3'—C4'	−176.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21B···O21′^i	0.88 (2)	2.11 (2)	2.917 (3)	152 (3)
N21—H21A···O21′	0.89 (2)	2.20 (2)	3.072 (4)	165 (3)
N1′—H1′···N3	0.88 (4)	1.96 (4)	2.836 (4)	171 (3)
N41′—H41B···N3′^ii	0.88 (2)	2.09 (2)	2.967 (4)	173 (3)
N41′—H41A···N1^iii	0.90 (2)	2.25 (2)	3.136 (3)	168 (3)

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

(II) ;

Crystal data

C6H9N3O2	F(000) = 328
Mr = 155.16	Dx = 1.399 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2797 reflections
a = 7.9835 (14) Å	θ = 3.4–25.8°
b = 10.0664 (12) Å	µ = 0.11 mm^−1
c = 9.8380 (16) Å	T = 173 K
β = 111.266 (13)°	Block, colourless
V = 736.8 (2) Å^3	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection

STOE IPDS II two-circle- diffractometer	1081 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.075
Graphite monochromator	θmax = 25.6°, θmin = 3.4°
ω scans	h = −9→9
4148 measured reflections	k = −12→12
1378 independent reflections	l = −11→11

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0753P)^2] where P = (Fo^2 + 2Fc^2)/3
1378 reflections	(Δ/σ)max < 0.001
107 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. ;

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	0.3040 (2)	0.43048 (16)	0.60310 (15)	0.0234 (4)
H1	0.212 (4)	0.481 (2)	0.565 (3)	0.045 (7)*
C2	0.4778 (2)	0.47782 (19)	0.65179 (17)	0.0230 (4)
C3	0.5985 (2)	0.35708 (18)	0.70209 (19)	0.0256 (4)
H3A	0.6802	0.3480	0.6473	0.031*
H3B	0.6706	0.3618	0.8077	0.031*
N4	0.46996 (19)	0.24849 (15)	0.66956 (16)	0.0255 (4)
C5	0.2999 (2)	0.29309 (18)	0.61126 (17)	0.0216 (4)
O21	0.52338 (16)	0.59333 (14)	0.65255 (13)	0.0310 (4)
C41	0.5179 (3)	0.10924 (19)	0.6973 (2)	0.0303 (4)
H41A	0.6392	0.1020	0.7710	0.046*	0.74 (2)
H41B	0.5146	0.0666	0.6068	0.046*	0.74 (2)
H41C	0.4321	0.0652	0.7327	0.046*	0.74 (2)
H41D	0.4181	0.0539	0.6360	0.046*	0.26 (2)
H41E	0.5426	0.0892	0.8002	0.046*	0.26 (2)
H41F	0.6252	0.0907	0.6743	0.046*	0.26 (2)
N51	0.16103 (19)	0.21043 (15)	0.56779 (15)	0.0234 (4)
C52	−0.0100 (2)	0.26064 (17)	0.53375 (17)	0.0221 (4)
C53	−0.1580 (2)	0.16038 (18)	0.4718 (2)	0.0276 (4)
H53A	−0.1880	0.1208	0.5511	0.041*
H53B	−0.1179	0.0906	0.4211	0.041*
H53C	−0.2644	0.2044	0.4029	0.041*
O54	−0.04656 (17)	0.37642 (13)	0.55588 (15)	0.0329 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0179 (8)	0.0221 (9)	0.0268 (7)	0.0029 (6)	0.0041 (6)	0.0015 (6)
C2	0.0204 (9)	0.0276 (10)	0.0202 (8)	−0.0025 (7)	0.0061 (6)	−0.0007 (6)
C3	0.0192 (9)	0.0271 (11)	0.0281 (9)	−0.0004 (7)	0.0056 (7)	0.0036 (7)
N4	0.0181 (7)	0.0240 (9)	0.0308 (8)	0.0021 (6)	0.0046 (6)	0.0029 (6)
C5	0.0215 (9)	0.0220 (10)	0.0208 (8)	0.0030 (7)	0.0071 (6)	−0.0004 (6)
O21	0.0252 (7)	0.0282 (8)	0.0359 (7)	−0.0043 (5)	0.0067 (5)	−0.0005 (5)
C41	0.0227 (9)	0.0290 (11)	0.0372 (10)	0.0060 (8)	0.0083 (7)	0.0046 (8)
N51	0.0191 (7)	0.0213 (9)	0.0278 (7)	0.0012 (6)	0.0061 (6)	−0.0010 (6)
C52	0.0214 (9)	0.0222 (10)	0.0219 (8)	0.0006 (7)	0.0067 (7)	0.0022 (6)
C53	0.0206 (9)	0.0279 (11)	0.0312 (9)	−0.0022 (7)	0.0056 (7)	−0.0015 (7)
O54	0.0205 (7)	0.0228 (7)	0.0521 (8)	0.0023 (5)	0.0092 (6)	−0.0013 (6)

Geometric parameters (Å, º)

N1—C2	1.378 (2)	C41—H41B	0.9800
N1—C5	1.386 (2)	C41—H41C	0.9800
N1—H1	0.86 (3)	C41—H41D	0.9800
C2—O21	1.218 (2)	C41—H41E	0.9799
C2—C3	1.518 (2)	C41—H41F	0.9800
C3—N4	1.453 (2)	N51—C52	1.379 (2)
C3—H3A	0.9900	C52—O54	1.240 (2)
C3—H3B	0.9900	C52—C53	1.504 (2)
N4—C5	1.345 (2)	C53—H53A	0.9800
N4—C41	1.453 (2)	C53—H53B	0.9800
C5—N51	1.327 (2)	C53—H53C	0.9800
C41—H41A	0.9800
C2—N1—C5	111.50 (14)	N4—C41—H41B	109.5
C2—N1—H1	122.6 (17)	N4—C41—H41C	109.5
C5—N1—H1	125.7 (17)	N4—C41—H41D	109.5
O21—C2—N1	126.41 (16)	N4—C41—H41E	109.5
O21—C2—C3	127.55 (15)	H41D—C41—H41E	109.5
N1—C2—C3	106.05 (15)	N4—C41—H41F	109.5
N4—C3—C2	102.51 (14)	H41D—C41—H41F	109.5
N4—C3—H3A	111.3	H41E—C41—H41F	109.5
C2—C3—H3A	111.3	C5—N51—C52	119.12 (16)
N4—C3—H3B	111.3	O54—C52—N51	125.27 (16)
C2—C3—H3B	111.3	O54—C52—C53	120.12 (15)
H3A—C3—H3B	109.2	N51—C52—C53	114.55 (15)
C5—N4—C41	123.95 (15)	C52—C53—H53A	109.5
C5—N4—C3	111.44 (15)	C52—C53—H53B	109.5
C41—N4—C3	124.60 (14)	H53A—C53—H53B	109.5
N51—C5—N4	121.62 (17)	C52—C53—H53C	109.5
N51—C5—N1	129.88 (15)	H53A—C53—H53C	109.5
N4—C5—N1	108.46 (14)	H53B—C53—H53C	109.5
N4—C41—H41A	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O54^i	0.86 (3)	2.02 (3)	2.849 (2)	162 (2)
N1—H1···O54	0.86 (3)	2.29 (2)	2.720 (2)	111.0 (19)

Symmetry code: (i) −x, −y+1, −z+1.

(III)

Crystal data

2(C4H4FN3O)·C6H9N3O2	Z = 2
Mr = 413.37	F(000) = 428
Triclinic, P1	Dx = 1.531 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.6548 (12) Å	Cell parameters from 4645 reflections
b = 9.3233 (14) Å	θ = 3.4–25.8°
c = 12.848 (2) Å	µ = 0.13 mm^−1
α = 83.406 (12)°	T = 173 K
β = 83.529 (12)°	Block, yellow
γ = 81.420 (12)°	0.30 × 0.30 × 0.20 mm
V = 896.4 (2) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	2293 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.122
Graphite monochromator	θmax = 25.7°, θmin = 3.4°
ω scans	h = −9→9
7962 measured reflections	k = −10→11
3344 independent reflections	l = −15→15

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)] = 0.063	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0933P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
3344 reflections	Δρmax = 0.33 e Å^−3
286 parameters	Δρmin = −0.31 e Å^−3
6 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: 0.021 (5)

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
N1A	0.8779 (3)	0.1895 (2)	0.68014 (19)	0.0283 (5)
H1A	0.851 (4)	0.275 (2)	0.642 (2)	0.034*
C2A	0.8488 (4)	0.0703 (3)	0.6316 (2)	0.0272 (6)
N3A	0.9005 (3)	−0.0662 (2)	0.67878 (18)	0.0284 (5)
C4A	0.9784 (4)	−0.0854 (3)	0.7679 (2)	0.0254 (6)
C5A	1.0118 (4)	0.0391 (3)	0.8149 (2)	0.0283 (6)
C6A	0.9609 (4)	0.1729 (3)	0.7700 (2)	0.0278 (6)
H6A	0.9824	0.2560	0.8005	0.033*
O21A	0.7758 (3)	0.0894 (2)	0.54864 (16)	0.0358 (5)
N41A	1.0276 (3)	−0.2208 (3)	0.8109 (2)	0.0329 (6)
H411	1.068 (4)	−0.238 (4)	0.8742 (18)	0.040*
H412	0.985 (4)	−0.287 (3)	0.781 (2)	0.040*
F51A	1.0990 (2)	0.01573 (19)	0.90320 (14)	0.0404 (5)
N1B	0.8276 (3)	0.7119 (2)	0.56716 (18)	0.0263 (5)
H1B	0.859 (4)	0.776 (3)	0.606 (2)	0.032*
C2B	0.8475 (4)	0.5737 (3)	0.6186 (2)	0.0238 (6)
N3B	0.8026 (3)	0.4628 (2)	0.57096 (17)	0.0247 (5)
C4B	0.7343 (3)	0.4869 (3)	0.4784 (2)	0.0252 (6)
C5B	0.7110 (4)	0.6329 (3)	0.4273 (2)	0.0285 (6)
C6B	0.7578 (4)	0.7424 (3)	0.4733 (2)	0.0273 (6)
H6B	0.7422	0.8395	0.4405	0.033*
O21B	0.9087 (3)	0.5502 (2)	0.70644 (14)	0.0270 (4)
N41B	0.6909 (3)	0.3749 (3)	0.4360 (2)	0.0305 (6)
H413	0.641 (4)	0.385 (4)	0.3775 (18)	0.037*
H414	0.704 (4)	0.287 (2)	0.471 (2)	0.037*
F51B	0.6411 (3)	0.65692 (19)	0.33332 (13)	0.0422 (5)
N1	1.2947 (3)	−0.5685 (2)	1.09748 (18)	0.0258 (5)
H1	1.272 (4)	−0.551 (3)	1.163 (3)	0.031*
C2	1.2242 (4)	−0.4888 (3)	1.0123 (2)	0.0261 (6)
C3	1.2933 (4)	−0.5712 (3)	0.9180 (2)	0.0296 (6)
H3A	1.1950	−0.6005	0.8849	0.035*
H3B	1.3638	−0.5123	0.8647	0.035*
N4	1.4041 (3)	−0.6978 (3)	0.96428 (18)	0.0302 (6)
C5	1.4010 (4)	−0.6961 (3)	1.0688 (2)	0.0264 (6)
O21	1.1245 (3)	−0.3734 (2)	1.01437 (16)	0.0352 (5)
C41	1.5061 (5)	−0.8120 (4)	0.9051 (3)	0.0449 (8)
H41A	1.6030	−0.8624	0.9451	0.067*
H41B	1.5556	−0.7684	0.8372	0.067*
H41C	1.4285	−0.8819	0.8933	0.067*
N51	1.4814 (3)	−0.8027 (2)	1.13081 (18)	0.0296 (5)
C52	1.5123 (3)	−0.7770 (3)	1.2295 (2)	0.0264 (6)
C53	1.5633 (4)	−0.9113 (3)	1.3020 (2)	0.0319 (7)
H53A	1.6526	−0.8927	1.3459	0.048*
H53B	1.6123	−0.9923	1.2604	0.048*
H53C	1.4581	−0.9366	1.3472	0.048*
O54	1.5066 (3)	−0.6533 (2)	1.25920 (15)	0.0307 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0368 (13)	0.0159 (11)	0.0324 (13)	−0.0018 (10)	−0.0070 (10)	−0.0029 (9)
C2A	0.0329 (15)	0.0180 (13)	0.0313 (15)	−0.0049 (11)	−0.0043 (12)	−0.0024 (11)
N3A	0.0375 (13)	0.0177 (11)	0.0304 (12)	−0.0030 (10)	−0.0076 (10)	−0.0013 (9)
C4A	0.0276 (14)	0.0203 (13)	0.0273 (14)	−0.0020 (11)	−0.0017 (11)	−0.0006 (11)
C5A	0.0294 (14)	0.0297 (15)	0.0269 (14)	−0.0034 (12)	−0.0058 (11)	−0.0058 (12)
C6A	0.0312 (14)	0.0233 (14)	0.0301 (14)	−0.0041 (11)	−0.0026 (11)	−0.0083 (11)
O21A	0.0536 (13)	0.0215 (10)	0.0347 (11)	−0.0070 (9)	−0.0159 (10)	0.0013 (8)
N41A	0.0425 (15)	0.0245 (13)	0.0326 (13)	−0.0025 (11)	−0.0137 (11)	0.0009 (11)
F51A	0.0510 (11)	0.0377 (10)	0.0355 (10)	−0.0024 (8)	−0.0198 (8)	−0.0058 (8)
N1B	0.0372 (13)	0.0149 (11)	0.0270 (12)	−0.0026 (10)	−0.0037 (10)	−0.0040 (9)
C2B	0.0297 (14)	0.0172 (12)	0.0238 (13)	−0.0012 (11)	0.0001 (11)	−0.0047 (10)
N3B	0.0324 (12)	0.0172 (11)	0.0252 (11)	−0.0027 (9)	−0.0022 (9)	−0.0062 (9)
C4B	0.0253 (14)	0.0226 (13)	0.0275 (14)	0.0000 (11)	−0.0023 (11)	−0.0057 (11)
C5B	0.0373 (16)	0.0247 (14)	0.0239 (14)	−0.0025 (12)	−0.0072 (12)	−0.0023 (11)
C6B	0.0362 (15)	0.0183 (13)	0.0253 (14)	0.0003 (11)	−0.0020 (11)	0.0004 (10)
O21B	0.0375 (11)	0.0202 (9)	0.0240 (10)	−0.0022 (8)	−0.0072 (8)	−0.0041 (7)
N41B	0.0408 (14)	0.0222 (12)	0.0307 (13)	−0.0050 (11)	−0.0118 (11)	−0.0032 (10)
F51B	0.0656 (12)	0.0315 (9)	0.0320 (10)	−0.0044 (9)	−0.0216 (9)	0.0002 (7)
N1	0.0345 (13)	0.0206 (11)	0.0218 (11)	0.0013 (10)	−0.0049 (10)	−0.0050 (9)
C2	0.0313 (14)	0.0234 (14)	0.0251 (14)	−0.0063 (12)	−0.0059 (11)	−0.0021 (11)
C3	0.0335 (15)	0.0314 (15)	0.0250 (14)	−0.0070 (12)	−0.0062 (11)	−0.0015 (12)
N4	0.0381 (14)	0.0268 (12)	0.0252 (12)	0.0002 (10)	−0.0037 (10)	−0.0063 (10)
C5	0.0346 (15)	0.0222 (14)	0.0241 (13)	−0.0069 (12)	−0.0029 (11)	−0.0054 (11)
O21	0.0428 (12)	0.0281 (11)	0.0335 (11)	0.0031 (10)	−0.0110 (9)	−0.0007 (9)
C41	0.055 (2)	0.0449 (19)	0.0326 (16)	0.0058 (16)	−0.0009 (15)	−0.0157 (15)
N51	0.0402 (14)	0.0198 (12)	0.0286 (12)	0.0019 (10)	−0.0067 (10)	−0.0057 (9)
C52	0.0250 (14)	0.0240 (14)	0.0300 (14)	−0.0011 (11)	−0.0008 (11)	−0.0069 (11)
C53	0.0373 (16)	0.0249 (15)	0.0327 (15)	−0.0015 (12)	−0.0068 (12)	−0.0003 (12)
O54	0.0385 (11)	0.0229 (10)	0.0322 (11)	−0.0023 (9)	−0.0105 (9)	−0.0043 (8)

Geometric parameters (Å, º)

N1A—C6A	1.362 (4)	C6B—H6B	0.9500
N1A—C2A	1.392 (3)	N41B—H413	0.870 (18)
N1A—H1A	0.898 (18)	N41B—H414	0.885 (18)
C2A—O21A	1.242 (3)	N1—C2	1.367 (4)
C2A—N3A	1.367 (4)	N1—C5	1.398 (4)
N3A—C4A	1.332 (4)	N1—H1	0.86 (3)
C4A—N41A	1.336 (4)	C2—O21	1.224 (4)
C4A—C5A	1.436 (4)	C2—C3	1.512 (4)
C5A—C6A	1.335 (4)	C3—N4	1.456 (4)
C5A—F51A	1.361 (3)	C3—H3A	0.9900
C6A—H6A	0.9500	C3—H3B	0.9900
N41A—H411	0.891 (18)	N4—C5	1.343 (4)
N41A—H412	0.886 (18)	N4—C41	1.458 (4)
N1B—C6B	1.357 (4)	C5—N51	1.322 (4)
N1B—C2B	1.374 (3)	C41—H41A	0.9800
N1B—H1B	0.898 (18)	C41—H41B	0.9800
C2B—O21B	1.255 (3)	C41—H41C	0.9800
C2B—N3B	1.364 (3)	N51—C52	1.369 (4)
N3B—C4B	1.336 (4)	C52—O54	1.249 (3)
C4B—N41B	1.331 (3)	C52—C53	1.502 (4)
C4B—C5B	1.436 (4)	C53—H53A	0.9800
C5B—C6B	1.348 (4)	C53—H53B	0.9800
C5B—F51B	1.357 (3)	C53—H53C	0.9800
C6A—N1A—C2A	121.8 (2)	C4B—N41B—H414	120 (2)
C6A—N1A—H1A	124 (2)	H413—N41B—H414	117 (3)
C2A—N1A—H1A	113 (2)	C2—N1—C5	111.3 (2)
O21A—C2A—N3A	121.8 (2)	C2—N1—H1	127 (2)
O21A—C2A—N1A	120.1 (2)	C5—N1—H1	121 (2)
N3A—C2A—N1A	118.1 (2)	O21—C2—N1	125.4 (3)
C4A—N3A—C2A	121.3 (2)	O21—C2—C3	127.9 (3)
N3A—C4A—N41A	119.2 (2)	N1—C2—C3	106.7 (2)
N3A—C4A—C5A	119.7 (2)	N4—C3—C2	102.4 (2)
N41A—C4A—C5A	121.1 (3)	N4—C3—H3A	111.3
C6A—C5A—F51A	122.1 (2)	C2—C3—H3A	111.3
C6A—C5A—C4A	119.6 (3)	N4—C3—H3B	111.3
F51A—C5A—C4A	118.3 (2)	C2—C3—H3B	111.3
C5A—C6A—N1A	119.5 (2)	H3A—C3—H3B	109.2
C5A—C6A—H6A	120.2	C5—N4—C3	111.4 (2)
N1A—C6A—H6A	120.2	C5—N4—C41	124.0 (3)
C4A—N41A—H411	122 (2)	C3—N4—C41	124.6 (2)
C4A—N41A—H412	113 (2)	N51—C5—N4	123.7 (3)
H411—N41A—H412	123 (3)	N51—C5—N1	128.1 (2)
C6B—N1B—C2B	122.2 (2)	N4—C5—N1	108.2 (2)
C6B—N1B—H1B	127 (2)	N4—C41—H41A	109.5
C2B—N1B—H1B	111 (2)	N4—C41—H41B	109.5
O21B—C2B—N3B	121.0 (2)	H41A—C41—H41B	109.5
O21B—C2B—N1B	120.5 (2)	N4—C41—H41C	109.5
N3B—C2B—N1B	118.5 (2)	H41A—C41—H41C	109.5
C4B—N3B—C2B	121.5 (2)	H41B—C41—H41C	109.5
N41B—C4B—N3B	119.0 (2)	C5—N51—C52	119.5 (2)
N41B—C4B—C5B	122.1 (2)	O54—C52—N51	124.6 (3)
N3B—C4B—C5B	118.9 (2)	O54—C52—C53	120.4 (2)
C6B—C5B—F51B	121.5 (3)	N51—C52—C53	114.9 (2)
C6B—C5B—C4B	119.8 (3)	C52—C53—H53A	109.5
F51B—C5B—C4B	118.7 (2)	C52—C53—H53B	109.5
C5B—C6B—N1B	119.0 (2)	H53A—C53—H53B	109.5
C5B—C6B—H6B	120.5	C52—C53—H53C	109.5
N1B—C6B—H6B	120.5	H53A—C53—H53C	109.5
C4B—N41B—H413	123 (2)	H53B—C53—H53C	109.5
C6A—N1A—C2A—O21A	−178.6 (3)	N41B—C4B—C5B—F51B	0.6 (4)
C6A—N1A—C2A—N3A	2.3 (4)	N3B—C4B—C5B—F51B	−179.8 (2)
O21A—C2A—N3A—C4A	−179.9 (3)	F51B—C5B—C6B—N1B	−179.8 (3)
N1A—C2A—N3A—C4A	−0.8 (4)	C4B—C5B—C6B—N1B	0.5 (4)
C2A—N3A—C4A—N41A	−179.6 (3)	C2B—N1B—C6B—C5B	−1.9 (4)
C2A—N3A—C4A—C5A	−1.0 (4)	C5—N1—C2—O21	179.0 (3)
N3A—C4A—C5A—C6A	1.4 (4)	C5—N1—C2—C3	−0.9 (3)
N41A—C4A—C5A—C6A	−180.0 (3)	O21—C2—C3—N4	179.9 (3)
N3A—C4A—C5A—F51A	−177.0 (2)	N1—C2—C3—N4	−0.2 (3)
N41A—C4A—C5A—F51A	1.6 (4)	C2—C3—N4—C5	1.2 (3)
F51A—C5A—C6A—N1A	178.4 (3)	C2—C3—N4—C41	−178.6 (3)
C4A—C5A—C6A—N1A	0.0 (4)	C3—N4—C5—N51	175.7 (2)
C2A—N1A—C6A—C5A	−1.9 (4)	C41—N4—C5—N51	−4.5 (5)
C6B—N1B—C2B—O21B	−178.3 (3)	C3—N4—C5—N1	−1.8 (3)
C6B—N1B—C2B—N3B	3.0 (4)	C41—N4—C5—N1	178.0 (3)
O21B—C2B—N3B—C4B	178.7 (2)	C2—N1—C5—N51	−175.7 (3)
N1B—C2B—N3B—C4B	−2.6 (4)	C2—N1—C5—N4	1.7 (3)
C2B—N3B—C4B—N41B	−179.2 (2)	N4—C5—N51—C52	162.6 (3)
C2B—N3B—C4B—C5B	1.2 (4)	N1—C5—N51—C52	−20.4 (4)
N41B—C4B—C5B—C6B	−179.7 (3)	C5—N51—C52—O54	−16.6 (4)
N3B—C4B—C5B—C6B	−0.1 (4)	C5—N51—C52—C53	166.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N3B	0.90 (2)	1.88 (2)	2.778 (3)	175 (3)
N41A—H412···O21B^i	0.89 (2)	2.07 (2)	2.950 (3)	175 (3)
N41A—H411···O21	0.89 (2)	2.13 (2)	2.946 (3)	153 (3)
N1B—H1B···N3A^ii	0.90 (2)	1.91 (2)	2.802 (3)	171 (3)
N41B—H414···O21A	0.89 (2)	2.02 (2)	2.901 (3)	171 (3)
N41B—H413···O54^iii	0.87 (2)	2.02 (2)	2.862 (3)	162 (3)
N1—H1···O21B^iv	0.86 (3)	2.06 (3)	2.817 (3)	147 (3)

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

(IV)

Crystal data

C4H4FN3O·C4H5N3O2	F(000) = 1056
Mr = 256.21	Dx = 1.650 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9090 reflections
a = 15.5508 (15) Å	θ = 3.5–25.9°
b = 11.7839 (7) Å	µ = 0.14 mm^−1
c = 11.4971 (12) Å	T = 173 K
β = 101.660 (8)°	Block, colourless
V = 2063.4 (3) Å^3	0.60 × 0.30 × 0.30 mm
Z = 8

Data collection

STOE IPDS II two-circle- diffractometer	1507 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.159
Graphite monochromator	θmax = 25.6°, θmin = 3.5°
ω scans	h = −18→18
15020 measured reflections	k = −14→14
1935 independent reflections	l = −13→12

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.0472P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
1935 reflections	Δρmax = 0.27 e Å^−3
192 parameters	Δρmin = −0.21 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: 0.0018 (5)

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	0.16314 (8)	0.50672 (12)	0.75001 (12)	0.0208 (3)
H1	0.1913 (12)	0.5430 (16)	0.6998 (17)	0.027 (5)*
C2	0.12106 (10)	0.57338 (13)	0.81866 (14)	0.0225 (4)
N3	0.07348 (8)	0.51746 (11)	0.88880 (12)	0.0210 (3)
H3	0.0437 (13)	0.5558 (18)	0.940 (2)	0.047 (6)*
C4	0.06432 (9)	0.39869 (13)	0.89298 (13)	0.0179 (3)
C5	0.10933 (9)	0.33537 (13)	0.81943 (13)	0.0192 (3)
H5	0.1049	0.2550	0.8176	0.023*
C6	0.15942 (9)	0.38941 (13)	0.75059 (13)	0.0177 (3)
O21	0.12809 (8)	0.67801 (10)	0.81616 (11)	0.0347 (3)
O41	0.01841 (7)	0.35882 (9)	0.96112 (10)	0.0231 (3)
N61	0.20757 (9)	0.33771 (13)	0.68126 (13)	0.0242 (3)
H61A	0.2167 (15)	0.262 (2)	0.687 (2)	0.061 (7)*
H61B	0.2456 (15)	0.3776 (19)	0.645 (2)	0.054 (7)*
N1'	0.32668 (8)	0.65165 (11)	0.45465 (12)	0.0206 (3)
H1'	0.3047 (13)	0.7292 (18)	0.4427 (18)	0.043 (6)*
C2'	0.29644 (9)	0.58530 (13)	0.53727 (14)	0.0184 (3)
N3'	0.32273 (8)	0.47538 (10)	0.55340 (12)	0.0189 (3)
C4'	0.37820 (9)	0.43197 (12)	0.48934 (14)	0.0190 (3)
C5'	0.40613 (10)	0.50005 (15)	0.40088 (14)	0.0231 (4)
C6'	0.38086 (10)	0.60923 (14)	0.38535 (14)	0.0231 (4)
H6'	0.4001	0.6554	0.3279	0.028*
O21'	0.24496 (7)	0.62932 (9)	0.59645 (10)	0.0236 (3)
N41'	0.40715 (9)	0.32627 (12)	0.50794 (14)	0.0250 (3)
H41C	0.4458 (14)	0.2995 (18)	0.4658 (19)	0.043 (6)*
H41D	0.3913 (14)	0.2850 (18)	0.567 (2)	0.045 (6)*
F51'	0.46007 (7)	0.45133 (9)	0.33608 (9)	0.0374 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0262 (7)	0.0175 (7)	0.0238 (7)	−0.0028 (5)	0.0169 (6)	0.0003 (5)
C2	0.0280 (8)	0.0178 (8)	0.0255 (8)	−0.0023 (6)	0.0146 (7)	−0.0011 (6)
N3	0.0266 (7)	0.0166 (7)	0.0247 (7)	−0.0002 (5)	0.0167 (6)	0.0007 (5)
C4	0.0175 (7)	0.0182 (7)	0.0198 (8)	−0.0022 (6)	0.0080 (6)	0.0010 (6)
C5	0.0209 (7)	0.0146 (7)	0.0246 (8)	−0.0016 (6)	0.0106 (6)	−0.0006 (6)
C6	0.0177 (7)	0.0184 (8)	0.0181 (8)	−0.0009 (6)	0.0064 (6)	−0.0020 (6)
O21	0.0549 (8)	0.0150 (6)	0.0445 (7)	−0.0040 (5)	0.0349 (6)	−0.0002 (5)
O41	0.0263 (6)	0.0204 (6)	0.0282 (6)	−0.0035 (4)	0.0189 (5)	0.0008 (5)
N61	0.0268 (7)	0.0203 (7)	0.0311 (8)	−0.0010 (6)	0.0190 (6)	−0.0026 (6)
N1'	0.0228 (7)	0.0187 (7)	0.0239 (7)	0.0013 (5)	0.0134 (5)	0.0041 (5)
C2'	0.0190 (7)	0.0180 (8)	0.0204 (8)	−0.0002 (6)	0.0094 (6)	0.0009 (6)
N3'	0.0208 (6)	0.0149 (6)	0.0240 (7)	−0.0003 (5)	0.0119 (5)	−0.0001 (5)
C4'	0.0194 (7)	0.0179 (8)	0.0217 (8)	−0.0017 (6)	0.0086 (6)	−0.0028 (6)
C5'	0.0226 (8)	0.0280 (8)	0.0232 (8)	0.0050 (6)	0.0154 (7)	−0.0009 (7)
C6'	0.0239 (7)	0.0252 (8)	0.0240 (8)	0.0005 (7)	0.0138 (6)	0.0054 (7)
O21'	0.0288 (6)	0.0172 (6)	0.0308 (6)	0.0029 (4)	0.0201 (5)	0.0022 (5)
N41'	0.0294 (8)	0.0182 (7)	0.0333 (8)	0.0036 (6)	0.0207 (6)	0.0004 (6)
F51'	0.0477 (6)	0.0375 (6)	0.0376 (6)	0.0156 (5)	0.0337 (5)	0.0064 (5)

Geometric parameters (Å, º)

N1—C2	1.370 (2)	N1'—C6'	1.366 (2)
N1—C6	1.384 (2)	N1'—C2'	1.384 (2)
N1—H1	0.90 (2)	N1'—H1'	0.98 (2)
C2—O21	1.239 (2)	C2'—O21'	1.2622 (18)
C2—N3	1.369 (2)	C2'—N3'	1.3597 (19)
N3—C4	1.4085 (19)	N3'—C4'	1.3433 (19)
N3—H3	0.93 (2)	C4'—N41'	1.327 (2)
C4—O41	1.2531 (18)	C4'—C5'	1.430 (2)
C4—C5	1.415 (2)	C5'—C6'	1.346 (2)
C5—C6	1.374 (2)	C5'—F51'	1.3569 (18)
C5—H5	0.9500	C6'—H6'	0.9500
C6—N61	1.345 (2)	N41'—H41C	0.90 (2)
N61—H61A	0.90 (2)	N41'—H41D	0.91 (2)
N61—H61B	0.92 (3)
C2—N1—C6	123.01 (13)	H61A—N61—H61B	115 (2)
C2—N1—H1	116.7 (12)	C6'—N1'—C2'	121.93 (14)
C6—N1—H1	120.2 (12)	C6'—N1'—H1'	120.0 (12)
O21—C2—N3	123.62 (15)	C2'—N1'—H1'	117.9 (12)
O21—C2—N1	120.18 (14)	O21'—C2'—N3'	121.60 (14)
N3—C2—N1	116.19 (14)	O21'—C2'—N1'	118.58 (13)
C2—N3—C4	124.68 (13)	N3'—C2'—N1'	119.82 (13)
C2—N3—H3	122.2 (13)	C4'—N3'—C2'	119.78 (13)
C4—N3—H3	113.1 (13)	N41'—C4'—N3'	120.24 (14)
O41—C4—N3	117.92 (13)	N41'—C4'—C5'	119.94 (14)
O41—C4—C5	126.10 (14)	N3'—C4'—C5'	119.81 (13)
N3—C4—C5	115.98 (13)	C6'—C5'—F51'	121.85 (15)
C6—C5—C4	120.43 (14)	C6'—C5'—C4'	120.52 (14)
C6—C5—H5	119.8	F51'—C5'—C4'	117.61 (14)
C4—C5—H5	119.8	C5'—C6'—N1'	118.05 (15)
N61—C6—C5	125.44 (15)	C5'—C6'—H6'	121.0
N61—C6—N1	114.90 (14)	N1'—C6'—H6'	121.0
C5—C6—N1	119.66 (14)	C4'—N41'—H41C	118.9 (14)
C6—N61—H61A	120.4 (16)	C4'—N41'—H41D	119.2 (13)
C6—N61—H61B	121.7 (14)	H41C—N41'—H41D	121.6 (19)
C6—N1—C2—O21	178.62 (15)	C6'—N1'—C2'—N3'	1.9 (2)
C6—N1—C2—N3	−0.5 (2)	O21'—C2'—N3'—C4'	−179.43 (13)
O21—C2—N3—C4	179.83 (15)	N1'—C2'—N3'—C4'	0.3 (2)
N1—C2—N3—C4	−1.1 (2)	C2'—N3'—C4'—N41'	177.16 (14)
C2—N3—C4—O41	−179.74 (13)	C2'—N3'—C4'—C5'	−2.8 (2)
C2—N3—C4—C5	0.9 (2)	N41'—C4'—C5'—C6'	−176.55 (15)
O41—C4—C5—C6	−178.43 (14)	N3'—C4'—C5'—C6'	3.4 (2)
N3—C4—C5—C6	0.9 (2)	N41'—C4'—C5'—F51'	2.0 (2)
C4—C5—C6—N61	177.24 (14)	N3'—C4'—C5'—F51'	−178.07 (13)
C4—C5—C6—N1	−2.4 (2)	F51'—C5'—C6'—N1'	−179.78 (13)
C2—N1—C6—N61	−177.43 (14)	C4'—C5'—C6'—N1'	−1.3 (2)
C2—N1—C6—C5	2.2 (2)	C2'—N1'—C6'—C5'	−1.3 (2)
C6'—N1'—C2'—O21'	−178.42 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O21′	0.90 (2)	1.88 (2)	2.7805 (17)	175.4 (17)
N3—H3···O41^i	0.93 (2)	1.92 (2)	2.8534 (17)	176.9 (19)
N61—H61A···O21^ii	0.90 (2)	2.62 (2)	3.1691 (18)	120.6 (18)
N61—H61B···N3′	0.92 (3)	2.09 (3)	3.011 (2)	175.2 (19)
N1′—H1′···O21′^iii	0.98 (2)	1.85 (2)	2.8256 (17)	173.3 (18)
N41′—H41C···O41^iv	0.90 (2)	2.19 (2)	2.9012 (17)	135.7 (18)
N41′—H41D···O21^ii	0.91 (2)	1.91 (2)	2.809 (2)	169.7 (19)

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1/2, −y+3/2, −z+1; (iv) x+1/2, −y+1/2, z−1/2.

(Va) ;

Crystal data

C4H4FN3O·C4H6N4O·H2O	Z = 2
Mr = 273.25	F(000) = 284
Triclinic, P1	Dx = 1.590 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.3280 (12) Å	Cell parameters from 4119 reflections
b = 9.3484 (14) Å	θ = 4.2–25.8°
c = 9.4779 (15) Å	µ = 0.14 mm^−1
α = 61.797 (11)°	T = 173 K
β = 64.500 (11)°	Block, colourless
γ = 67.138 (11)°	0.30 × 0.30 × 0.15 mm
V = 570.83 (15) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	1615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.093
Graphite monochromator	θmax = 25.6°, θmin = 4.2°
ω scans	h = −10→10
6264 measured reflections	k = −11→11
2124 independent reflections	l = −11→11

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0752P)^2] where P = (Fo^2 + 2Fc^2)/3
2124 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

Experimental. ;

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	0.4542 (2)	0.49058 (18)	0.21825 (19)	0.0214 (3)
C2	0.5311 (2)	0.3707 (2)	0.3352 (2)	0.0191 (4)
N3	0.6523 (2)	0.39393 (18)	0.38002 (19)	0.0186 (3)
H3	0.710 (3)	0.313 (3)	0.449 (3)	0.024 (5)*
C4	0.7017 (2)	0.5455 (2)	0.3086 (2)	0.0179 (4)
C5	0.6179 (2)	0.6743 (2)	0.1893 (2)	0.0209 (4)
H5	0.6407	0.7825	0.1394	0.025*
C6	0.5003 (2)	0.6412 (2)	0.1446 (2)	0.0211 (4)
N21	0.4939 (2)	0.2205 (2)	0.4120 (2)	0.0254 (4)
H21A	0.418 (3)	0.205 (3)	0.379 (3)	0.030 (6)*
H21B	0.543 (3)	0.148 (3)	0.485 (3)	0.018 (5)*
O41	0.81837 (17)	0.55197 (15)	0.35703 (16)	0.0230 (3)
N61	0.4195 (2)	0.7584 (2)	0.0255 (2)	0.0302 (4)
H61A	0.359 (4)	0.726 (3)	−0.009 (3)	0.046 (7)*
H61B	0.462 (4)	0.845 (4)	−0.044 (4)	0.050 (7)*
N1'	0.8816 (2)	−0.17077 (18)	0.79064 (19)	0.0226 (4)
H1'	0.863 (3)	−0.267 (3)	0.817 (3)	0.035 (6)*
C2'	0.7879 (2)	−0.0327 (2)	0.6881 (2)	0.0203 (4)
N3'	0.8326 (2)	0.11684 (17)	0.62066 (19)	0.0196 (3)
C4'	0.9599 (2)	0.1308 (2)	0.6617 (2)	0.0188 (4)
C5'	1.0513 (2)	−0.0124 (2)	0.7734 (2)	0.0231 (4)
C6'	1.0130 (2)	−0.1612 (2)	0.8345 (2)	0.0231 (4)
H6'	1.0751	−0.2574	0.9063	0.028*
O21'	0.66311 (18)	−0.04823 (15)	0.65977 (18)	0.0294 (4)
N41'	0.9996 (2)	0.2786 (2)	0.5969 (2)	0.0252 (4)
H41C	0.932 (3)	0.361 (3)	0.531 (3)	0.040 (7)*
H41D	1.087 (4)	0.288 (3)	0.624 (3)	0.041 (6)*
F51'	1.17736 (16)	0.00835 (15)	0.81322 (16)	0.0366 (3)
O1W	0.16623 (19)	0.49137 (15)	0.12840 (17)	0.0240 (3)
H1WA	0.064 (4)	0.517 (3)	0.202 (3)	0.038 (6)*
H1WB	0.252 (4)	0.489 (3)	0.163 (3)	0.033 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0196 (7)	0.0248 (8)	0.0226 (8)	−0.0078 (6)	−0.0099 (6)	−0.0055 (6)
C2	0.0153 (8)	0.0225 (9)	0.0209 (9)	−0.0031 (6)	−0.0057 (7)	−0.0098 (7)
N3	0.0180 (7)	0.0168 (8)	0.0230 (8)	−0.0038 (6)	−0.0114 (7)	−0.0046 (6)
C4	0.0154 (8)	0.0200 (9)	0.0210 (9)	−0.0045 (6)	−0.0046 (7)	−0.0101 (7)
C5	0.0206 (9)	0.0191 (9)	0.0216 (9)	−0.0073 (7)	−0.0061 (7)	−0.0046 (7)
C6	0.0183 (9)	0.0233 (9)	0.0186 (9)	−0.0034 (7)	−0.0056 (7)	−0.0066 (7)
N21	0.0287 (9)	0.0203 (8)	0.0341 (9)	−0.0083 (7)	−0.0201 (8)	−0.0037 (7)
O41	0.0239 (7)	0.0219 (7)	0.0299 (7)	−0.0076 (5)	−0.0137 (6)	−0.0079 (6)
N61	0.0327 (9)	0.0290 (9)	0.0278 (9)	−0.0109 (7)	−0.0193 (8)	0.0024 (7)
N1'	0.0253 (8)	0.0164 (8)	0.0263 (8)	−0.0083 (6)	−0.0118 (7)	−0.0018 (7)
C2'	0.0204 (9)	0.0188 (9)	0.0225 (9)	−0.0065 (7)	−0.0080 (7)	−0.0052 (7)
N3'	0.0207 (8)	0.0171 (7)	0.0233 (8)	−0.0057 (6)	−0.0108 (6)	−0.0044 (6)
C4'	0.0178 (8)	0.0200 (8)	0.0218 (9)	−0.0047 (6)	−0.0073 (7)	−0.0088 (7)
C5'	0.0217 (9)	0.0250 (9)	0.0275 (10)	−0.0052 (7)	−0.0133 (8)	−0.0085 (8)
C6'	0.0229 (9)	0.0201 (9)	0.0233 (9)	−0.0027 (7)	−0.0122 (8)	−0.0029 (7)
O21'	0.0325 (7)	0.0212 (7)	0.0421 (8)	−0.0118 (5)	−0.0233 (7)	−0.0025 (6)
N41'	0.0291 (9)	0.0202 (8)	0.0341 (9)	−0.0083 (7)	−0.0196 (8)	−0.0049 (7)
F51'	0.0408 (7)	0.0318 (6)	0.0506 (8)	−0.0099 (5)	−0.0355 (6)	−0.0049 (5)
O1W	0.0204 (7)	0.0247 (7)	0.0278 (7)	−0.0065 (5)	−0.0098 (6)	−0.0072 (6)

Geometric parameters (Å, º)

N1—C2	1.332 (2)	N1'—C6'	1.372 (2)
N1—C6	1.370 (2)	N1'—C2'	1.380 (2)
C2—N21	1.332 (2)	N1'—H1'	0.87 (3)
C2—N3	1.368 (2)	C2'—O21'	1.252 (2)
N3—C4	1.394 (2)	C2'—N3'	1.363 (2)
N3—H3	0.87 (2)	N3'—C4'	1.342 (2)
C4—O41	1.270 (2)	C4'—N41'	1.332 (2)
C4—C5	1.398 (3)	C4'—C5'	1.433 (3)
C5—C6	1.397 (2)	C5'—C6'	1.340 (3)
C5—H5	0.9500	C5'—F51'	1.3607 (19)
C6—N61	1.356 (2)	C6'—H6'	0.9500
N21—H21A	0.90 (2)	N41'—H41C	0.90 (3)
N21—H21B	0.83 (2)	N41'—H41D	0.92 (3)
N61—H61A	0.90 (3)	O1W—H1WA	0.87 (3)
N61—H61B	0.86 (3)	O1W—H1WB	0.89 (3)
C2—N1—C6	116.85 (15)	H61A—N61—H61B	117 (2)
N21—C2—N1	120.43 (16)	C6'—N1'—C2'	122.12 (14)
N21—C2—N3	117.18 (16)	C6'—N1'—H1'	121.1 (16)
N1—C2—N3	122.38 (15)	C2'—N1'—H1'	116.4 (16)
C2—N3—C4	122.42 (15)	O21'—C2'—N3'	121.64 (15)
C2—N3—H3	122.4 (14)	O21'—C2'—N1'	118.93 (15)
C4—N3—H3	115.0 (14)	N3'—C2'—N1'	119.43 (15)
O41—C4—N3	117.09 (15)	C4'—N3'—C2'	119.89 (14)
O41—C4—C5	126.95 (15)	N41'—C4'—N3'	119.04 (16)
N3—C4—C5	115.96 (15)	N41'—C4'—C5'	120.99 (16)
C6—C5—C4	118.91 (15)	N3'—C4'—C5'	119.96 (15)
C6—C5—H5	120.5	C6'—C5'—F51'	121.86 (16)
C4—C5—H5	120.5	C6'—C5'—C4'	120.31 (16)
N61—C6—N1	114.50 (16)	F51'—C5'—C4'	117.82 (15)
N61—C6—C5	122.10 (16)	C5'—C6'—N1'	118.18 (16)
N1—C6—C5	123.39 (16)	C5'—C6'—H6'	120.9
C2—N21—H21A	116.8 (14)	N1'—C6'—H6'	120.9
C2—N21—H21B	118.8 (13)	C4'—N41'—H41C	114.3 (15)
H21A—N21—H21B	124 (2)	C4'—N41'—H41D	119.3 (15)
C6—N61—H61A	118.2 (16)	H41C—N41'—H41D	126 (2)
C6—N61—H61B	119.6 (18)	H1WA—O1W—H1WB	104 (2)
C6—N1—C2—N21	−179.64 (16)	C6'—N1'—C2'—N3'	3.4 (3)
C6—N1—C2—N3	−0.7 (3)	O21'—C2'—N3'—C4'	176.12 (16)
N21—C2—N3—C4	−179.93 (16)	N1'—C2'—N3'—C4'	−3.6 (3)
N1—C2—N3—C4	1.1 (3)	C2'—N3'—C4'—N41'	−178.83 (17)
C2—N3—C4—O41	−178.51 (15)	C2'—N3'—C4'—C5'	1.3 (3)
C2—N3—C4—C5	0.8 (2)	N41'—C4'—C5'—C6'	−178.44 (18)
O41—C4—C5—C6	176.26 (17)	N3'—C4'—C5'—C6'	1.4 (3)
N3—C4—C5—C6	−3.0 (2)	N41'—C4'—C5'—F51'	1.1 (3)
C2—N1—C6—N61	179.47 (16)	N3'—C4'—C5'—F51'	−179.07 (15)
C2—N1—C6—C5	−1.7 (3)	F51'—C5'—C6'—N1'	178.81 (16)
C4—C5—C6—N61	−177.61 (17)	C4'—C5'—C6'—N1'	−1.7 (3)
C4—C5—C6—N1	3.6 (3)	C2'—N1'—C6'—C5'	−0.7 (3)
C6'—N1'—C2'—O21'	−176.37 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N3′	0.87 (2)	2.05 (3)	2.917 (2)	176 (2)
N61—H61B···O21′^i	0.86 (3)	2.51 (3)	3.205 (2)	139 (2)
N21—H21A···O21′^ii	0.90 (2)	2.05 (2)	2.864 (2)	150 (2)
N21—H21B···O21′	0.83 (2)	2.06 (2)	2.887 (2)	174.9 (19)
N1′—H1′···O1W^ii	0.87 (3)	1.99 (3)	2.867 (2)	177 (2)
N41′—H41C···O41	0.90 (3)	2.01 (3)	2.906 (2)	171 (2)
N41′—H41D···O41^iii	0.92 (3)	2.04 (3)	2.8441 (19)	145 (2)
O1W—H1WA···O41^iv	0.87 (3)	1.95 (3)	2.809 (2)	170 (2)
O1W—H1WB···N1	0.89 (3)	1.97 (3)	2.8661 (19)	175 (2)

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

(Vb) ;

Crystal data

C4H4FN3O·C4H6N4O·C3H7NO	Z = 2
Mr = 328.33	F(000) = 344
Triclinic, P1	Dx = 1.454 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0866 (14) Å	Cell parameters from 4256 reflections
b = 9.3632 (15) Å	θ = 3.4–25.8°
c = 9.4019 (15) Å	µ = 0.12 mm^−1
α = 104.720 (13)°	T = 173 K
β = 94.340 (13)°	Block, yellow
γ = 102.010 (13)°	0.60 × 0.60 × 0.30 mm
V = 749.7 (2) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	1593 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.080
Graphite monochromator	θmax = 25.6°, θmin = 3.4°
ω scans	h = −11→11
8452 measured reflections	k = −11→11
2806 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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0457P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.89	(Δ/σ)max < 0.001
2806 reflections	Δρmax = 0.29 e Å^−3
235 parameters	Δρmin = −0.22 e Å^−3
8 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: 0.014 (3)

Special details

Experimental. ;

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	0.3660 (2)	0.5069 (3)	0.8344 (3)	0.0261 (5)
C2	0.4758 (3)	0.5363 (3)	0.7533 (3)	0.0234 (6)
N3	0.4821 (2)	0.6406 (3)	0.6742 (2)	0.0221 (5)
H3	0.558 (2)	0.656 (3)	0.621 (3)	0.027*
C4	0.3748 (3)	0.7289 (3)	0.6762 (3)	0.0231 (6)
C5	0.2592 (3)	0.7008 (3)	0.7621 (3)	0.0236 (6)
H5	0.1820	0.7559	0.7687	0.028*
C6	0.2587 (3)	0.5904 (3)	0.8384 (3)	0.0241 (6)
N21	0.5867 (3)	0.4611 (3)	0.7460 (3)	0.0340 (6)
H21A	0.665 (3)	0.484 (4)	0.698 (3)	0.041*
H21B	0.588 (3)	0.405 (3)	0.809 (3)	0.041*
O41	0.3948 (2)	0.8275 (2)	0.6039 (2)	0.0297 (5)
N61	0.1525 (3)	0.5615 (3)	0.9271 (3)	0.0369 (7)
H61A	0.077 (3)	0.608 (3)	0.935 (3)	0.044*
H61B	0.145 (3)	0.485 (3)	0.967 (3)	0.044*
N1'	0.9716 (2)	0.6619 (3)	0.4433 (3)	0.0251 (5)
H1'	1.036 (3)	0.603 (3)	0.437 (3)	0.030*
C2'	0.8537 (3)	0.6394 (3)	0.5239 (3)	0.0212 (6)
N3'	0.7497 (2)	0.7255 (3)	0.5292 (2)	0.0234 (5)
C4'	0.7644 (3)	0.8337 (3)	0.4570 (3)	0.0215 (6)
C5'	0.8897 (3)	0.8582 (3)	0.3763 (3)	0.0218 (6)
C6'	0.9893 (3)	0.7702 (3)	0.3682 (3)	0.0246 (6)
H6'	1.0707	0.7829	0.3113	0.030*
O21'	0.84386 (19)	0.5392 (2)	0.5930 (2)	0.0274 (5)
N41'	0.6598 (3)	0.9150 (3)	0.4633 (3)	0.0289 (6)
H41A	0.671 (3)	0.991 (3)	0.421 (3)	0.035*
H41B	0.578 (2)	0.891 (3)	0.506 (3)	0.035*
F51'	0.90390 (16)	0.97161 (18)	0.30756 (17)	0.0287 (4)
O1A	−0.0914 (2)	0.7263 (2)	0.9818 (2)	0.0357 (5)
C2A	−0.1240 (3)	0.8222 (3)	0.9225 (3)	0.0304 (7)
H2A	−0.0590	0.8534	0.8560	0.036*
N3A	−0.2422 (2)	0.8849 (3)	0.9441 (2)	0.0269 (5)
C4A	−0.2661 (3)	1.0005 (4)	0.8702 (3)	0.0364 (7)
H4A1	−0.1845	1.0193	0.8101	0.055*
H4A2	−0.2657	1.0949	0.9452	0.055*
H4A3	−0.3641	0.9643	0.8061	0.055*
C5A	−0.3518 (3)	0.8447 (4)	1.0413 (3)	0.0334 (7)
H5A1	−0.3417	0.9313	1.1288	0.050*
H5A2	−0.3326	0.7575	1.0729	0.050*
H5A3	−0.4549	0.8184	0.9878	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0218 (11)	0.0275 (13)	0.0376 (13)	0.0113 (10)	0.0108 (9)	0.0179 (11)
C2	0.0202 (12)	0.0198 (15)	0.0344 (16)	0.0070 (11)	0.0064 (11)	0.0122 (13)
N3	0.0187 (11)	0.0245 (13)	0.0314 (13)	0.0096 (10)	0.0137 (9)	0.0157 (11)
C4	0.0214 (13)	0.0225 (15)	0.0297 (15)	0.0114 (11)	0.0064 (11)	0.0091 (13)
C5	0.0206 (12)	0.0233 (15)	0.0314 (15)	0.0093 (12)	0.0085 (11)	0.0109 (13)
C6	0.0171 (12)	0.0235 (16)	0.0340 (16)	0.0035 (11)	0.0069 (10)	0.0119 (13)
N21	0.0251 (12)	0.0352 (15)	0.0588 (18)	0.0164 (11)	0.0204 (12)	0.0314 (14)
O41	0.0293 (10)	0.0296 (12)	0.0438 (12)	0.0153 (9)	0.0152 (9)	0.0243 (10)
N61	0.0307 (13)	0.0403 (17)	0.0581 (17)	0.0183 (12)	0.0262 (12)	0.0326 (14)
N1'	0.0210 (11)	0.0245 (13)	0.0383 (13)	0.0128 (10)	0.0118 (10)	0.0156 (11)
C2'	0.0200 (12)	0.0217 (15)	0.0273 (14)	0.0096 (11)	0.0111 (10)	0.0102 (12)
N3'	0.0210 (11)	0.0240 (13)	0.0320 (13)	0.0114 (9)	0.0092 (9)	0.0134 (11)
C4'	0.0214 (12)	0.0210 (15)	0.0242 (14)	0.0085 (11)	0.0044 (10)	0.0071 (12)
C5'	0.0236 (13)	0.0220 (15)	0.0236 (14)	0.0062 (11)	0.0077 (10)	0.0111 (12)
C6'	0.0218 (13)	0.0243 (16)	0.0306 (15)	0.0048 (12)	0.0112 (11)	0.0108 (13)
O21'	0.0263 (9)	0.0272 (11)	0.0409 (12)	0.0149 (8)	0.0155 (8)	0.0209 (10)
N41'	0.0262 (12)	0.0318 (14)	0.0432 (15)	0.0181 (11)	0.0189 (10)	0.0229 (12)
F51'	0.0297 (8)	0.0269 (9)	0.0378 (9)	0.0081 (7)	0.0098 (6)	0.0209 (8)
O1A	0.0327 (10)	0.0359 (12)	0.0481 (13)	0.0156 (10)	0.0118 (9)	0.0207 (11)
C2A	0.0278 (14)	0.0300 (16)	0.0332 (17)	0.0060 (12)	0.0083 (12)	0.0082 (14)
N3A	0.0278 (12)	0.0260 (14)	0.0304 (13)	0.0102 (10)	0.0069 (9)	0.0099 (11)
C4A	0.0367 (16)	0.0302 (17)	0.0450 (19)	0.0083 (14)	0.0034 (13)	0.0154 (16)
C5A	0.0294 (14)	0.0418 (18)	0.0317 (16)	0.0107 (13)	0.0087 (12)	0.0122 (15)

Geometric parameters (Å, º)

N1—C2	1.326 (3)	N3'—C4'	1.346 (3)
N1—C6	1.367 (3)	C4'—N41'	1.331 (3)
C2—N21	1.341 (3)	C4'—C5'	1.427 (4)
C2—N3	1.365 (3)	C5'—C6'	1.339 (3)
N3—C4	1.401 (3)	C5'—F51'	1.366 (3)
N3—H3	0.889 (17)	C6'—H6'	0.9500
C4—O41	1.271 (3)	N41'—H41A	0.892 (17)
C4—C5	1.395 (4)	N41'—H41B	0.889 (17)
C5—C6	1.400 (4)	O1A—C2A	1.243 (3)
C5—H5	0.9500	C2A—N3A	1.332 (3)
C6—N61	1.352 (3)	C2A—H2A	0.9500
N21—H21A	0.890 (18)	N3A—C5A	1.458 (3)
N21—H21B	0.883 (17)	N3A—C4A	1.469 (3)
N61—H61A	0.886 (18)	C4A—H4A1	0.9800
N61—H61B	0.887 (18)	C4A—H4A2	0.9800
N1'—C6'	1.366 (3)	C4A—H4A3	0.9800
N1'—C2'	1.370 (3)	C5A—H5A1	0.9800
N1'—H1'	0.879 (17)	C5A—H5A2	0.9800
C2'—O21'	1.262 (3)	C5A—H5A3	0.9800
C2'—N3'	1.360 (3)
C2—N1—C6	116.3 (2)	N41'—C4'—C5'	121.9 (2)
N1—C2—N21	119.8 (2)	N3'—C4'—C5'	119.8 (2)
N1—C2—N3	123.0 (2)	C6'—C5'—F51'	121.5 (2)
N21—C2—N3	117.1 (2)	C6'—C5'—C4'	120.0 (2)
C2—N3—C4	122.3 (2)	F51'—C5'—C4'	118.5 (2)
C2—N3—H3	119.5 (17)	C5'—C6'—N1'	118.7 (2)
C4—N3—H3	118.1 (17)	C5'—C6'—H6'	120.6
O41—C4—C5	127.1 (2)	N1'—C6'—H6'	120.6
O41—C4—N3	117.4 (2)	C4'—N41'—H41A	119.6 (19)
C5—C4—N3	115.5 (2)	C4'—N41'—H41B	120.1 (19)
C4—C5—C6	119.0 (2)	H41A—N41'—H41B	120 (3)
C4—C5—H5	120.5	O1A—C2A—N3A	125.6 (3)
C6—C5—H5	120.5	O1A—C2A—H2A	117.2
N61—C6—N1	114.4 (2)	N3A—C2A—H2A	117.2
N61—C6—C5	121.7 (2)	C2A—N3A—C5A	122.6 (2)
N1—C6—C5	123.8 (2)	C2A—N3A—C4A	120.4 (3)
C2—N21—H21A	121 (2)	C5A—N3A—C4A	117.0 (2)
C2—N21—H21B	115 (2)	N3A—C4A—H4A1	109.5
H21A—N21—H21B	122 (3)	N3A—C4A—H4A2	109.5
C6—N61—H61A	121 (2)	H4A1—C4A—H4A2	109.5
C6—N61—H61B	122 (2)	N3A—C4A—H4A3	109.5
H61A—N61—H61B	116 (3)	H4A1—C4A—H4A3	109.5
C6'—N1'—C2'	121.8 (2)	H4A2—C4A—H4A3	109.5
C6'—N1'—H1'	119.1 (19)	N3A—C5A—H5A1	109.5
C2'—N1'—H1'	119.0 (19)	N3A—C5A—H5A2	109.5
O21'—C2'—N3'	121.0 (2)	H5A1—C5A—H5A2	109.5
O21'—C2'—N1'	119.3 (2)	N3A—C5A—H5A3	109.5
N3'—C2'—N1'	119.8 (2)	H5A1—C5A—H5A3	109.5
C4'—N3'—C2'	119.8 (2)	H5A2—C5A—H5A3	109.5
N41'—C4'—N3'	118.3 (2)
C6—N1—C2—N21	178.8 (3)	O21'—C2'—N3'—C4'	178.6 (3)
C6—N1—C2—N3	−1.6 (4)	N1'—C2'—N3'—C4'	−1.0 (4)
N1—C2—N3—C4	2.1 (4)	C2'—N3'—C4'—N41'	179.4 (2)
N21—C2—N3—C4	−178.3 (3)	C2'—N3'—C4'—C5'	−0.5 (4)
C2—N3—C4—O41	176.9 (3)	N41'—C4'—C5'—C6'	−177.5 (3)
C2—N3—C4—C5	−1.3 (4)	N3'—C4'—C5'—C6'	2.3 (4)
O41—C4—C5—C6	−177.8 (3)	N41'—C4'—C5'—F51'	2.0 (4)
N3—C4—C5—C6	0.2 (4)	N3'—C4'—C5'—F51'	−178.2 (2)
C2—N1—C6—N61	−177.4 (3)	F51'—C5'—C6'—N1'	177.9 (2)
C2—N1—C6—C5	0.6 (4)	C4'—C5'—C6'—N1'	−2.6 (4)
C4—C5—C6—N61	177.9 (3)	C2'—N1'—C6'—C5'	1.2 (4)
C4—C5—C6—N1	0.1 (4)	O1A—C2A—N3A—C5A	−1.0 (4)
C6'—N1'—C2'—O21'	−179.0 (3)	O1A—C2A—N3A—C4A	178.3 (3)
C6'—N1'—C2'—N3'	0.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N3′	0.89 (2)	2.06 (2)	2.941 (3)	170 (3)
N61—H61A···O1A	0.89 (2)	2.08 (2)	2.958 (3)	173 (3)
N61—H61B···O1A^i	0.89 (2)	2.12 (2)	2.988 (3)	167 (3)
N21—H21A···O21′	0.89 (2)	2.01 (2)	2.898 (3)	179 (3)
N1′—H1′···O21′^ii	0.88 (2)	1.87 (2)	2.748 (3)	174 (3)
N41′—H41B···O41	0.89 (2)	2.02 (2)	2.904 (3)	177 (3)
N41′—H41A···O41^iii	0.89 (2)	1.97 (2)	2.772 (3)	148 (3)

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

(Vc) ;

Crystal data

2(C4H4FN3O)·2(C4H6N4O)·C3H7NO	Z = 1
Mr = 583.56	F(000) = 304
Triclinic, P1	Dx = 1.463 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1894 (12) Å	Cell parameters from 3942 reflections
b = 10.0991 (15) Å	θ = 3.7–25.8°
c = 10.9953 (19) Å	µ = 0.12 mm^−1
α = 104.97 (1)°	T = 173 K
β = 105.33 (1)°	Block, yellow
γ = 110.85 (1)°	0.50 × 0.50 × 0.40 mm
V = 662.22 (19) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	1665 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.074
Graphite monochromator	θmax = 25.6°, θmin = 3.5°
ω scans	h = −8→8
7507 measured reflections	k = −12→12
2475 independent reflections	l = −13→13

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0889P)^2 + 0.0624P] where P = (Fo^2 + 2Fc^2)/3
2475 reflections	(Δ/σ)max < 0.001
242 parameters	Δρmax = 0.29 e Å^−3
11 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. ;

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	0.8427 (4)	0.5383 (3)	0.8547 (3)	0.0226 (6)
C2	0.8119 (4)	0.6116 (3)	0.7732 (3)	0.0192 (6)
N3	0.6191 (4)	0.6122 (3)	0.7173 (3)	0.0213 (6)
H3	0.603 (6)	0.663 (4)	0.661 (4)	0.042 (10)*
C4	0.4361 (5)	0.5313 (3)	0.7384 (3)	0.0222 (7)
C5	0.4643 (5)	0.4485 (3)	0.8206 (3)	0.0237 (7)
H5	0.3458	0.3875	0.8370	0.028*
C6	0.6672 (5)	0.4564 (3)	0.8779 (3)	0.0216 (6)
N21	0.9765 (4)	0.6913 (3)	0.7435 (3)	0.0270 (6)
H21A	0.952 (6)	0.743 (4)	0.691 (4)	0.032 (9)*
H21B	1.087 (6)	0.674 (4)	0.758 (4)	0.029 (9)*
O41	0.2645 (3)	0.5405 (3)	0.6839 (2)	0.0290 (6)
N61	0.7038 (4)	0.3807 (3)	0.9595 (3)	0.0295 (7)
H61A	0.600 (5)	0.344 (4)	0.991 (4)	0.038 (10)*
H61B	0.841 (4)	0.408 (5)	1.005 (4)	0.054 (13)*
N1'	0.7108 (4)	0.9232 (3)	0.4227 (3)	0.0237 (6)
H1'	0.830 (5)	0.987 (4)	0.419 (5)	0.062 (13)*
C2'	0.7346 (5)	0.8577 (3)	0.5182 (3)	0.0223 (7)
N3'	0.5570 (4)	0.7709 (3)	0.5355 (3)	0.0212 (6)
C4'	0.3592 (5)	0.7466 (3)	0.4586 (3)	0.0198 (6)
C5'	0.3360 (5)	0.8122 (3)	0.3578 (3)	0.0223 (7)
C6'	0.5116 (5)	0.8997 (3)	0.3425 (3)	0.0236 (7)
H6'	0.4978	0.9446	0.2767	0.028*
O21'	0.9204 (3)	0.8796 (3)	0.5873 (3)	0.0319 (6)
N41'	0.1889 (4)	0.6647 (3)	0.4798 (3)	0.0254 (6)
H41A	0.054 (6)	0.622 (4)	0.415 (4)	0.028 (9)*
H41B	0.216 (6)	0.620 (4)	0.540 (4)	0.037 (10)*
F51'	0.1330 (3)	0.7845 (2)	0.2814 (2)	0.0328 (5)
O1A	0.3541 (13)	0.1276 (10)	0.9696 (11)	0.097 (3)	0.50
C2A	0.1657 (17)	0.1064 (10)	0.9424 (10)	0.062 (3)	0.50
H2A	0.1114	0.1501	0.8836	0.075*	0.50
N3A	0.0349 (16)	0.0273 (10)	0.9892 (10)	0.049 (2)	0.50
C5A	0.093 (3)	−0.0374 (14)	1.0876 (12)	0.074 (4)	0.50
H5A1	0.2505	0.0049	1.1293	0.110*	0.50
H5A2	0.0275	−0.1496	1.0411	0.110*	0.50
H5A3	0.0388	−0.0115	1.1589	0.110*	0.50
C4A	−0.1900 (19)	0.0065 (17)	0.9477 (16)	0.086 (4)	0.50
H4A1	−0.1996	0.0872	0.9164	0.129*	0.50
H4A2	−0.2320	0.0131	1.0261	0.129*	0.50
H4A3	−0.2876	−0.0946	0.8731	0.129*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0199 (12)	0.0259 (13)	0.0256 (15)	0.0111 (11)	0.0079 (11)	0.0156 (12)
C2	0.0200 (14)	0.0190 (14)	0.0209 (16)	0.0105 (12)	0.0080 (12)	0.0089 (13)
N3	0.0200 (13)	0.0261 (13)	0.0268 (15)	0.0128 (11)	0.0105 (11)	0.0191 (12)
C4	0.0192 (14)	0.0260 (15)	0.0217 (17)	0.0102 (12)	0.0085 (13)	0.0094 (14)
C5	0.0225 (15)	0.0278 (16)	0.0253 (18)	0.0114 (13)	0.0103 (13)	0.0163 (14)
C6	0.0257 (15)	0.0220 (15)	0.0213 (17)	0.0130 (13)	0.0106 (13)	0.0102 (13)
N21	0.0208 (14)	0.0357 (15)	0.0374 (18)	0.0165 (12)	0.0138 (12)	0.0259 (14)
O41	0.0203 (11)	0.0388 (13)	0.0394 (15)	0.0166 (10)	0.0133 (10)	0.0263 (12)
N61	0.0266 (15)	0.0412 (16)	0.0324 (17)	0.0168 (13)	0.0131 (13)	0.0283 (14)
N1'	0.0218 (13)	0.0254 (13)	0.0304 (16)	0.0103 (11)	0.0119 (12)	0.0195 (12)
C2'	0.0209 (15)	0.0208 (15)	0.0282 (19)	0.0092 (12)	0.0093 (13)	0.0147 (14)
N3'	0.0209 (13)	0.0227 (13)	0.0246 (15)	0.0095 (11)	0.0103 (11)	0.0150 (11)
C4'	0.0202 (14)	0.0190 (14)	0.0228 (17)	0.0098 (12)	0.0097 (13)	0.0095 (13)
C5'	0.0208 (15)	0.0217 (15)	0.0233 (17)	0.0111 (13)	0.0042 (13)	0.0095 (13)
C6'	0.0264 (16)	0.0206 (15)	0.0235 (17)	0.0110 (13)	0.0069 (13)	0.0109 (13)
O21'	0.0176 (11)	0.0396 (13)	0.0473 (16)	0.0123 (10)	0.0110 (10)	0.0329 (12)
N41'	0.0163 (13)	0.0309 (14)	0.0305 (16)	0.0084 (11)	0.0075 (12)	0.0194 (13)
F51'	0.0232 (9)	0.0389 (11)	0.0377 (12)	0.0133 (8)	0.0053 (8)	0.0249 (10)
O1A	0.071 (5)	0.083 (6)	0.124 (8)	0.011 (4)	0.033 (5)	0.060 (6)
C2A	0.085 (8)	0.046 (5)	0.049 (6)	0.020 (5)	0.020 (6)	0.028 (5)
N3A	0.074 (7)	0.042 (7)	0.028 (4)	0.026 (6)	0.013 (4)	0.016 (4)
C5A	0.151 (14)	0.061 (7)	0.044 (7)	0.072 (9)	0.038 (8)	0.038 (6)
C4A	0.075 (9)	0.073 (8)	0.061 (10)	0.020 (7)	−0.002 (6)	0.003 (7)

Geometric parameters (Å, º)

N1—C2	1.324 (4)	N3'—C4'	1.344 (4)
N1—C6	1.371 (4)	C4'—N41'	1.330 (4)
C2—N21	1.348 (4)	C4'—C5'	1.434 (4)
C2—N3	1.363 (3)	C5'—C6'	1.341 (4)
N3—C4	1.396 (4)	C5'—F51'	1.361 (3)
N3—H3	0.91 (4)	C6'—H6'	0.9500
C4—O41	1.269 (3)	N41'—H41A	0.90 (4)
C4—C5	1.404 (4)	N41'—H41B	0.91 (4)
C5—C6	1.391 (4)	O1A—C2A	1.231 (11)
C5—H5	0.9500	C2A—N3A	1.311 (10)
C6—N61	1.353 (4)	C2A—H2A	0.9500
N21—H21A	0.90 (4)	N3A—C5A	1.446 (10)
N21—H21B	0.85 (4)	N3A—C4A	1.478 (14)
N61—H61A	0.902 (19)	C5A—H5A1	0.9800
N61—H61B	0.883 (19)	C5A—H5A2	0.9800
N1'—C6'	1.366 (4)	C5A—H5A3	0.9800
N1'—C2'	1.383 (4)	C4A—H4A1	0.9800
N1'—H1'	0.89 (2)	C4A—H4A2	0.9800
C2'—O21'	1.256 (4)	C4A—H4A3	0.9800
C2'—N3'	1.361 (4)
C2—N1—C6	116.8 (2)	C2'—N1'—H1'	118 (3)
N1—C2—N21	119.8 (2)	O21'—C2'—N3'	121.2 (2)
N1—C2—N3	123.0 (2)	O21'—C2'—N1'	119.1 (2)
N21—C2—N3	117.2 (2)	N3'—C2'—N1'	119.6 (2)
C2—N3—C4	122.3 (2)	C4'—N3'—C2'	120.2 (2)
C2—N3—H3	121 (2)	N41'—C4'—N3'	119.1 (3)
C4—N3—H3	117 (2)	N41'—C4'—C5'	121.2 (3)
O41—C4—N3	117.9 (2)	N3'—C4'—C5'	119.7 (2)
O41—C4—C5	126.8 (3)	C6'—C5'—F51'	122.1 (2)
N3—C4—C5	115.3 (2)	C6'—C5'—C4'	119.9 (3)
C6—C5—C4	119.5 (3)	F51'—C5'—C4'	118.0 (2)
C6—C5—H5	120.2	C5'—C6'—N1'	119.1 (3)
C4—C5—H5	120.2	C5'—C6'—H6'	120.4
N61—C6—N1	115.1 (2)	N1'—C6'—H6'	120.4
N61—C6—C5	121.9 (3)	C4'—N41'—H41A	121 (2)
N1—C6—C5	123.0 (2)	C4'—N41'—H41B	115 (2)
C2—N21—H21A	118 (2)	H41A—N41'—H41B	119 (3)
C2—N21—H21B	119 (2)	O1A—C2A—N3A	124.3 (9)
H21A—N21—H21B	122 (3)	O1A—C2A—H2A	117.8
C6—N61—H61A	116 (2)	N3A—C2A—H2A	117.8
C6—N61—H61B	115 (3)	C2A—N3A—C5A	125.8 (10)
H61A—N61—H61B	123 (4)	C2A—N3A—C4A	119.8 (10)
C6'—N1'—C2'	121.4 (2)	C5A—N3A—C4A	114.2 (8)
C6'—N1'—H1'	120 (3)
C6—N1—C2—N21	−178.4 (3)	O21'—C2'—N3'—C4'	−178.7 (3)
C6—N1—C2—N3	2.2 (4)	N1'—C2'—N3'—C4'	1.2 (4)
N1—C2—N3—C4	−2.0 (5)	C2'—N3'—C4'—N41'	−178.3 (3)
N21—C2—N3—C4	178.6 (3)	C2'—N3'—C4'—C5'	0.2 (4)
C2—N3—C4—O41	178.9 (3)	N41'—C4'—C5'—C6'	177.2 (3)
C2—N3—C4—C5	−0.4 (4)	N3'—C4'—C5'—C6'	−1.2 (4)
O41—C4—C5—C6	−177.0 (3)	N41'—C4'—C5'—F51'	−1.9 (4)
N3—C4—C5—C6	2.3 (4)	N3'—C4'—C5'—F51'	179.7 (3)
C2—N1—C6—N61	178.8 (3)	F51'—C5'—C6'—N1'	179.9 (3)
C2—N1—C6—C5	−0.2 (4)	C4'—C5'—C6'—N1'	0.8 (4)
C4—C5—C6—N61	179.0 (3)	C2'—N1'—C6'—C5'	0.6 (5)
C4—C5—C6—N1	−2.1 (5)	O1A—C2A—N3A—C5A	5.1 (19)
C6'—N1'—C2'—O21'	178.3 (3)	O1A—C2A—N3A—C4A	−178.8 (12)
C6'—N1'—C2'—N3'	−1.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N3′	0.91 (4)	2.00 (4)	2.907 (3)	178 (3)
N61—H61B···N1^i	0.88 (2)	2.16 (2)	3.031 (4)	169 (4)
N61—H61A···O1A	0.90 (2)	2.17 (3)	2.931 (8)	141 (3)
N21—H21B···O41^ii	0.85 (4)	2.31 (4)	3.080 (3)	150 (3)
N21—H21A···O21′	0.90 (4)	2.03 (4)	2.932 (3)	175 (3)
N1′—H1′···O21′^iii	0.89 (2)	1.85 (2)	2.742 (3)	179 (5)
N41′—H41B···O41	0.91 (4)	1.96 (4)	2.863 (3)	172 (3)
N41′—H41A···O41^iv	0.90 (4)	2.05 (4)	2.885 (4)	153 (3)

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

(Vd) ;

Crystal data

2(C4H4FN3O)·C4H6N4O·C3H7NO	Z = 6
Mr = 457.43	F(000) = 1428
Triclinic, P1	Dx = 1.501 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.2283 (11) Å	Cell parameters from 11994 reflections
b = 15.1837 (12) Å	θ = 3.4–25.7°
c = 18.8290 (17) Å	µ = 0.13 mm^−1
α = 71.262 (7)°	T = 173 K
β = 87.187 (8)°	Block, colourless
γ = 88.460 (7)°	0.30 × 0.20 × 0.15 mm
V = 3036.1 (5) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	5218 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.097
Graphite monochromator	θmax = 25.0°, θmin = 3.4°
ω scans	h = −13→13
32977 measured reflections	k = −18→18
10672 independent reflections	l = −22→18

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ^2(Fo^2) + (0.0533P)^2] where P = (Fo^2 + 2Fc^2)/3
10672 reflections	(Δ/σ)max = 0.001
981 parameters	Δρmax = 0.62 e Å^−3
33 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. ;

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)
N1A	−0.0441 (3)	0.5768 (2)	0.55522 (19)	0.0254 (8)
C2A	0.0027 (3)	0.6429 (2)	0.4964 (2)	0.0215 (9)
N3A	0.0053 (3)	0.7348 (2)	0.4930 (2)	0.0249 (8)
H3A	0.042 (4)	0.775 (3)	0.455 (2)	0.030*
C4A	−0.0462 (3)	0.7650 (2)	0.5502 (2)	0.0229 (9)
C5A	−0.0992 (4)	0.6971 (3)	0.6109 (2)	0.0263 (9)
H5A	−0.1383	0.7136	0.6508	0.032*
C6A	−0.0944 (3)	0.6038 (3)	0.6125 (2)	0.0231 (9)
N21A	0.0548 (3)	0.6212 (2)	0.4385 (2)	0.0260 (8)
H21A	0.053 (3)	0.5635 (15)	0.440 (2)	0.031*
H21B	0.090 (3)	0.662 (2)	0.3995 (16)	0.031*
O41A	−0.0372 (3)	0.85096 (17)	0.54260 (16)	0.0333 (7)
N61A	−0.1358 (3)	0.5337 (2)	0.6720 (2)	0.0343 (9)
H61A	−0.121 (4)	0.4760 (16)	0.676 (2)	0.041*
H61B	−0.183 (3)	0.541 (3)	0.7094 (18)	0.041*
N1B	0.2222 (3)	0.9053 (2)	0.24467 (19)	0.0257 (8)
H1B	0.257 (3)	0.883 (3)	0.2116 (18)	0.031*
C2B	0.1733 (3)	0.8403 (3)	0.3076 (2)	0.0223 (9)
N3B	0.1223 (3)	0.8689 (2)	0.36472 (18)	0.0224 (7)
C4B	0.1246 (3)	0.9593 (3)	0.3592 (2)	0.0238 (9)
C5B	0.1785 (4)	1.0249 (3)	0.2933 (2)	0.0286 (10)
C6B	0.2253 (4)	0.9973 (3)	0.2376 (2)	0.0293 (9)
H6B	0.2602	1.0409	0.1938	0.035*
O21B	0.1756 (2)	0.75601 (17)	0.31108 (15)	0.0293 (7)
N41B	0.0756 (3)	0.9858 (2)	0.4145 (2)	0.0305 (8)
H41A	0.042 (3)	0.947 (2)	0.4561 (16)	0.037*
H41B	0.069 (4)	1.0429 (16)	0.413 (2)	0.037*
F51B	0.1780 (2)	1.11572 (15)	0.29117 (14)	0.0415 (6)
N1C	0.4658 (3)	0.8843 (2)	0.0264 (2)	0.0297 (8)
H1C	0.513 (4)	0.924 (3)	−0.005 (3)	0.036*
C2C	0.3913 (4)	0.9083 (3)	0.0782 (2)	0.0293 (10)
N3C	0.3337 (3)	0.8400 (2)	0.13371 (19)	0.0264 (8)
C4C	0.3487 (3)	0.7496 (3)	0.1380 (2)	0.0251 (9)
C5C	0.4232 (4)	0.7275 (3)	0.0822 (2)	0.0303 (10)
C6C	0.4808 (4)	0.7945 (3)	0.0289 (2)	0.0292 (10)
H6C	0.5322	0.7794	−0.0072	0.035*
O21C	0.3769 (3)	0.99239 (18)	0.07300 (16)	0.0366 (7)
N41C	0.2942 (3)	0.6839 (2)	0.1935 (2)	0.0330 (9)
H41C	0.308 (4)	0.6252 (16)	0.197 (2)	0.040*
H41D	0.248 (3)	0.705 (3)	0.2250 (19)	0.040*
F51C	0.4374 (2)	0.63690 (16)	0.08649 (16)	0.0448 (7)
O1X	−0.2789 (3)	0.5192 (2)	0.80670 (18)	0.0482 (9)
N3X	−0.3413 (3)	0.6308 (2)	0.8579 (2)	0.0351 (9)
C2X	−0.3244 (5)	0.5407 (3)	0.8584 (3)	0.0286 (14)	0.771 (7)
H2X1	−0.3500	0.4921	0.9021	0.034*	0.771 (7)
C4X	−0.3906 (5)	0.6531 (4)	0.9202 (4)	0.0463 (19)	0.771 (7)
H4X1	−0.3952	0.7208	0.9081	0.070*	0.771 (7)
H4X2	−0.3401	0.6268	0.9631	0.070*	0.771 (7)
H4X3	−0.4708	0.6271	0.9328	0.070*	0.771 (7)
C5X	−0.3062 (5)	0.7056 (3)	0.7886 (3)	0.0326 (15)	0.771 (7)
H5X1	−0.3230	0.7661	0.7955	0.049*	0.771 (7)
H5X2	−0.3516	0.7005	0.7470	0.049*	0.771 (7)
H5X3	−0.2208	0.7001	0.7773	0.049*	0.771 (7)
C2X'	−0.291 (2)	0.6024 (8)	0.8061 (10)	0.090 (10)*	0.229 (7)
H2X2	−0.2606	0.6490	0.7627	0.109*	0.229 (7)
C4X'	−0.358 (3)	0.7282 (8)	0.8569 (14)	0.085 (9)*	0.229 (7)
H4X4	−0.4039	0.7292	0.9024	0.128*	0.229 (7)
H4X5	−0.4020	0.7633	0.8126	0.128*	0.229 (7)
H4X6	−0.2804	0.7566	0.8551	0.128*	0.229 (7)
C5X'	−0.3944 (17)	0.5692 (10)	0.9300 (7)	0.047 (6)*	0.229 (7)
H5X4	−0.4310	0.6072	0.9587	0.071*	0.229 (7)
H5X5	−0.3319	0.5293	0.9591	0.071*	0.229 (7)
H5X6	−0.4553	0.5303	0.9197	0.071*	0.229 (7)
N1D	0.7028 (3)	0.7928 (2)	0.12640 (18)	0.0215 (7)
C2D	0.6528 (3)	0.7259 (2)	0.1847 (2)	0.0196 (8)
N3D	0.6623 (3)	0.6342 (2)	0.19134 (19)	0.0247 (8)
H3D	0.615 (3)	0.596 (2)	0.2277 (17)	0.030*
C4D	0.7237 (3)	0.6024 (3)	0.1381 (2)	0.0243 (9)
C5D	0.7777 (3)	0.6705 (2)	0.0767 (2)	0.0239 (9)
H5D	0.8238	0.6537	0.0393	0.029*
C6D	0.7617 (3)	0.7633 (2)	0.0722 (2)	0.0219 (8)
N21D	0.5915 (3)	0.7493 (2)	0.23889 (19)	0.0255 (8)
H21C	0.546 (4)	0.708 (3)	0.271 (2)	0.031*
H21D	0.581 (3)	0.807 (3)	0.237 (2)	0.031*
O41D	0.7245 (3)	0.51477 (17)	0.14974 (16)	0.0348 (7)
N61D	0.8064 (3)	0.8330 (2)	0.0121 (2)	0.0306 (8)
H61C	0.774 (3)	0.8885 (18)	0.009 (2)	0.037*
H61D	0.840 (3)	0.820 (3)	−0.0279 (16)	0.037*
N1E	0.3985 (3)	0.4703 (2)	0.42283 (19)	0.0269 (8)
H1E	0.361 (3)	0.492 (3)	0.4561 (18)	0.032*
C2E	0.4600 (3)	0.5345 (2)	0.3650 (2)	0.0214 (8)
N3E	0.5166 (3)	0.5069 (2)	0.30935 (19)	0.0240 (7)
C4E	0.5088 (3)	0.4180 (3)	0.3117 (2)	0.0227 (9)
C5E	0.4438 (4)	0.3530 (3)	0.3708 (2)	0.0299 (10)
C6E	0.3897 (4)	0.3800 (3)	0.4264 (2)	0.0311 (10)
H6E	0.3467	0.3368	0.4669	0.037*
O21E	0.4632 (2)	0.61780 (17)	0.36430 (16)	0.0318 (7)
N41E	0.5654 (3)	0.3912 (2)	0.2571 (2)	0.0295 (8)
H41E	0.572 (4)	0.3310 (15)	0.263 (2)	0.035*
H41F	0.611 (3)	0.431 (2)	0.2220 (18)	0.035*
F51E	0.4403 (2)	0.26290 (15)	0.37137 (15)	0.0474 (7)
N1F	0.1815 (3)	0.4775 (2)	0.65690 (19)	0.0270 (8)
H1F	0.143 (3)	0.434 (2)	0.6934 (18)	0.032*
C2F	0.2345 (3)	0.4566 (3)	0.5962 (2)	0.0235 (9)
N3F	0.2898 (3)	0.5255 (2)	0.53908 (18)	0.0228 (7)
C4F	0.2904 (3)	0.6123 (3)	0.5421 (2)	0.0247 (9)
C5F	0.2371 (4)	0.6321 (3)	0.6056 (2)	0.0287 (9)
C6F	0.1832 (4)	0.5648 (3)	0.6615 (2)	0.0301 (10)
H6F	0.1468	0.5781	0.7036	0.036*
O21F	0.2317 (2)	0.37445 (17)	0.59444 (16)	0.0296 (7)
N41F	0.3398 (3)	0.6803 (2)	0.4851 (2)	0.0300 (8)
H41G	0.349 (3)	0.7381 (16)	0.484 (2)	0.036*
H41H	0.377 (3)	0.662 (3)	0.4499 (18)	0.036*
F51F	0.2428 (2)	0.72039 (15)	0.60862 (14)	0.0441 (7)
N1G	−0.4246 (3)	−0.0488 (2)	1.22579 (18)	0.0243 (7)
C2G	−0.3682 (3)	0.0157 (2)	1.1701 (2)	0.0206 (8)
N3G	−0.3612 (3)	0.1065 (2)	1.16810 (19)	0.0235 (7)
H3G	−0.311 (3)	0.143 (2)	1.1352 (18)	0.028*
C4G	−0.4129 (3)	0.1379 (3)	1.2248 (2)	0.0245 (9)
C5G	−0.4748 (3)	0.0718 (2)	1.2826 (2)	0.0263 (9)
H5G	−0.5146	0.0888	1.3220	0.032*
C6G	−0.4779 (3)	−0.0209 (3)	1.2821 (2)	0.0246 (9)
N21G	−0.3147 (3)	−0.0071 (2)	1.11295 (19)	0.0247 (8)
H21E	−0.267 (4)	0.037 (3)	1.080 (2)	0.030*
H21F	−0.312 (3)	−0.067 (3)	1.119 (2)	0.030*
O41G	−0.3985 (2)	0.22271 (17)	1.21802 (16)	0.0297 (7)
N61G	−0.5301 (3)	−0.0897 (2)	1.3384 (2)	0.0354 (9)
H61E	−0.536 (4)	−0.145 (3)	1.336 (3)	0.043*
H61F	−0.563 (4)	−0.078 (3)	1.378 (3)	0.043*
N1H	−0.0889 (3)	0.2675 (2)	0.94391 (19)	0.0231 (7)
H1H	−0.063 (3)	0.247 (3)	0.9075 (17)	0.028*
C2H	−0.1462 (3)	0.2056 (2)	1.0053 (2)	0.0197 (8)
N3H	−0.2103 (3)	0.2371 (2)	1.05526 (18)	0.0208 (7)
C4H	−0.2096 (3)	0.3296 (2)	1.0474 (2)	0.0233 (9)
C5H	−0.1428 (4)	0.3904 (2)	0.9868 (2)	0.0259 (9)
C6H	−0.0863 (3)	0.3595 (2)	0.9354 (2)	0.0244 (9)
H6H	−0.0449	0.4014	0.8934	0.029*
O21H	−0.1398 (2)	0.11947 (16)	1.01315 (15)	0.0270 (6)
N41H	−0.2748 (3)	0.3588 (2)	1.0970 (2)	0.0263 (8)
H41I	−0.310 (3)	0.318 (2)	1.1376 (16)	0.032*
H41J	−0.270 (3)	0.4188 (15)	1.091 (2)	0.032*
F51H	−0.1417 (2)	0.48298 (14)	0.98242 (14)	0.0364 (6)
N1I	0.1164 (3)	0.2437 (2)	0.71342 (19)	0.0253 (7)
H1I	0.152 (3)	0.281 (2)	0.6739 (16)	0.030*
C2I	0.0493 (3)	0.2689 (2)	0.7675 (2)	0.0220 (8)
N3I	0.0062 (3)	0.20124 (19)	0.82967 (17)	0.0205 (7)
C4I	0.0278 (3)	0.1110 (2)	0.8378 (2)	0.0229 (8)
C5I	0.0937 (3)	0.0872 (3)	0.7802 (2)	0.0254 (9)
C6I	0.1375 (3)	0.1527 (3)	0.7203 (2)	0.0239 (9)
H6I	0.1833	0.1363	0.6825	0.029*
O21I	0.0313 (2)	0.35301 (16)	0.75957 (15)	0.0290 (6)
N41I	−0.0149 (3)	0.0463 (2)	0.9004 (2)	0.0288 (8)
H41K	0.010 (3)	−0.0120 (16)	0.913 (2)	0.035*
H41L	−0.056 (3)	0.065 (3)	0.9357 (18)	0.035*
F51I	0.1104 (2)	−0.00583 (13)	0.78849 (13)	0.0335 (6)
O1Y	0.9097 (3)	0.7515 (2)	−0.09598 (17)	0.0431 (8)
C2Y	0.9754 (4)	0.7810 (3)	−0.1511 (3)	0.0320 (10)
H2Y	0.9947	0.8451	−0.1661	0.038*
N3Y	1.0233 (3)	0.7312 (2)	−0.19309 (19)	0.0269 (7)
C5Y	1.0016 (4)	0.6321 (3)	−0.1744 (3)	0.0371 (11)
H5Y1	0.9501	0.6111	−0.1287	0.056*
H5Y2	1.0776	0.5978	−0.1661	0.056*
H5Y3	0.9623	0.6205	−0.2159	0.056*
C4Y	1.0994 (4)	0.7756 (3)	−0.2594 (3)	0.0456 (12)
H4Y1	1.1066	0.8418	−0.2655	0.068*
H4Y2	1.0642	0.7687	−0.3039	0.068*
H4Y3	1.1786	0.7461	−0.2534	0.068*
O1Z	−0.6507 (3)	−0.1135 (2)	1.48097 (18)	0.0461 (8)
C2Z	−0.6969 (4)	−0.0844 (3)	1.5309 (3)	0.0430 (12)
H2Z	−0.7329	−0.1292	1.5735	0.052*
N3Z	−0.7005 (3)	0.0030 (2)	1.52978 (19)	0.0309 (8)
C4Z	−0.7581 (4)	0.0302 (3)	1.5903 (3)	0.0432 (12)
H4Z1	−0.7892	−0.0252	1.6293	0.065*
H4Z2	−0.8239	0.0735	1.5708	0.065*
H4Z3	−0.7001	0.0604	1.6118	0.065*
C5Z	−0.6522 (5)	0.0764 (3)	1.4661 (3)	0.0566 (14)
H5Z1	−0.6261	0.0508	1.4263	0.085*
H5Z2	−0.5841	0.1041	1.4813	0.085*
H5Z3	−0.7137	0.1243	1.4475	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.038 (2)	0.0166 (16)	0.0202 (19)	−0.0031 (14)	0.0044 (15)	−0.0053 (15)
C2A	0.031 (2)	0.0162 (18)	0.019 (2)	−0.0015 (16)	−0.0017 (18)	−0.0071 (18)
N3A	0.038 (2)	0.0159 (17)	0.0192 (19)	−0.0032 (14)	0.0094 (15)	−0.0051 (15)
C4A	0.034 (2)	0.0152 (19)	0.021 (2)	0.0021 (16)	0.0047 (18)	−0.0079 (17)
C5A	0.036 (2)	0.020 (2)	0.025 (2)	0.0019 (17)	0.0029 (18)	−0.0104 (18)
C6A	0.026 (2)	0.022 (2)	0.022 (2)	−0.0025 (16)	0.0036 (17)	−0.0099 (19)
N21A	0.040 (2)	0.0159 (17)	0.023 (2)	−0.0060 (15)	0.0074 (16)	−0.0083 (16)
O41A	0.0553 (19)	0.0151 (14)	0.0301 (17)	−0.0033 (13)	0.0113 (14)	−0.0099 (13)
N61A	0.055 (2)	0.0209 (18)	0.025 (2)	−0.0049 (16)	0.0186 (17)	−0.0070 (17)
N1B	0.037 (2)	0.0212 (17)	0.0176 (18)	−0.0051 (14)	0.0086 (15)	−0.0059 (15)
C2B	0.024 (2)	0.023 (2)	0.021 (2)	0.0009 (16)	−0.0018 (17)	−0.0096 (18)
N3B	0.0303 (18)	0.0172 (16)	0.0196 (18)	−0.0016 (13)	0.0030 (14)	−0.0063 (15)
C4B	0.027 (2)	0.023 (2)	0.021 (2)	−0.0039 (16)	−0.0009 (18)	−0.0066 (18)
C5B	0.040 (2)	0.0158 (19)	0.029 (2)	−0.0022 (17)	0.004 (2)	−0.0068 (19)
C6B	0.038 (2)	0.018 (2)	0.029 (2)	−0.0059 (17)	0.0060 (19)	−0.0035 (18)
O21B	0.0467 (17)	0.0188 (14)	0.0223 (16)	−0.0067 (12)	0.0077 (13)	−0.0073 (12)
N41B	0.048 (2)	0.0173 (17)	0.028 (2)	−0.0050 (16)	0.0079 (17)	−0.0099 (16)
F51B	0.0650 (17)	0.0154 (12)	0.0426 (16)	−0.0054 (11)	0.0122 (13)	−0.0090 (11)
N1C	0.035 (2)	0.030 (2)	0.022 (2)	0.0033 (15)	0.0083 (15)	−0.0057 (16)
C2C	0.036 (2)	0.025 (2)	0.020 (2)	0.0056 (18)	0.0049 (19)	−0.0010 (19)
N3C	0.0317 (18)	0.0232 (17)	0.0219 (19)	−0.0003 (14)	0.0042 (15)	−0.0045 (15)
C4C	0.027 (2)	0.026 (2)	0.023 (2)	−0.0002 (17)	−0.0013 (18)	−0.0092 (19)
C5C	0.034 (2)	0.029 (2)	0.035 (3)	0.0012 (19)	−0.002 (2)	−0.019 (2)
C6C	0.032 (2)	0.033 (2)	0.026 (2)	0.0002 (19)	0.0028 (19)	−0.014 (2)
O21C	0.0489 (18)	0.0218 (15)	0.0353 (18)	0.0042 (13)	0.0145 (14)	−0.0062 (13)
N41C	0.041 (2)	0.0241 (19)	0.036 (2)	−0.0035 (16)	0.0098 (18)	−0.0135 (18)
F51C	0.0547 (16)	0.0291 (13)	0.0572 (18)	−0.0091 (11)	0.0175 (13)	−0.0252 (13)
O1X	0.057 (2)	0.050 (2)	0.038 (2)	0.0062 (16)	0.0162 (16)	−0.0168 (17)
N3X	0.035 (2)	0.0255 (18)	0.039 (2)	−0.0063 (15)	−0.0009 (17)	−0.0015 (18)
C2X	0.044 (3)	0.017 (3)	0.026 (3)	−0.009 (2)	0.009 (3)	−0.009 (2)
C4X	0.047 (4)	0.053 (4)	0.056 (4)	0.002 (3)	0.005 (3)	−0.043 (4)
C5X	0.032 (3)	0.018 (3)	0.042 (4)	−0.003 (2)	0.004 (3)	−0.002 (3)
N1D	0.0289 (17)	0.0182 (16)	0.0190 (18)	−0.0012 (13)	0.0048 (14)	−0.0088 (14)
C2D	0.025 (2)	0.0142 (18)	0.019 (2)	−0.0026 (15)	0.0014 (17)	−0.0055 (17)
N3D	0.037 (2)	0.0151 (16)	0.0217 (19)	−0.0004 (14)	0.0078 (15)	−0.0074 (15)
C4D	0.031 (2)	0.024 (2)	0.022 (2)	0.0007 (16)	0.0027 (18)	−0.0138 (18)
C5D	0.033 (2)	0.0195 (19)	0.021 (2)	−0.0015 (16)	0.0070 (18)	−0.0098 (18)
C6D	0.027 (2)	0.0189 (19)	0.019 (2)	−0.0026 (16)	0.0048 (17)	−0.0046 (17)
N21D	0.040 (2)	0.0119 (16)	0.026 (2)	−0.0047 (14)	0.0152 (16)	−0.0093 (15)
O41D	0.0560 (19)	0.0121 (14)	0.0359 (18)	−0.0045 (12)	0.0134 (14)	−0.0089 (13)
N61D	0.046 (2)	0.0198 (17)	0.024 (2)	−0.0018 (15)	0.0129 (16)	−0.0069 (15)
N1E	0.035 (2)	0.0219 (18)	0.0236 (19)	−0.0037 (14)	0.0118 (15)	−0.0083 (15)
C2E	0.024 (2)	0.021 (2)	0.018 (2)	−0.0021 (16)	0.0070 (16)	−0.0049 (17)
N3E	0.0319 (18)	0.0168 (16)	0.0244 (19)	−0.0039 (13)	0.0046 (15)	−0.0087 (15)
C4E	0.025 (2)	0.020 (2)	0.024 (2)	−0.0013 (16)	0.0003 (17)	−0.0096 (18)
C5E	0.042 (2)	0.0151 (19)	0.033 (3)	−0.0088 (17)	0.007 (2)	−0.0088 (19)
C6E	0.041 (2)	0.020 (2)	0.030 (2)	−0.0106 (18)	0.006 (2)	−0.0052 (19)
O21E	0.0461 (18)	0.0204 (15)	0.0303 (17)	−0.0059 (12)	0.0131 (14)	−0.0119 (13)
N41E	0.043 (2)	0.0167 (17)	0.030 (2)	−0.0037 (15)	0.0092 (17)	−0.0110 (16)
F51E	0.0746 (18)	0.0188 (12)	0.0492 (18)	−0.0163 (12)	0.0251 (14)	−0.0143 (12)
N1F	0.038 (2)	0.0205 (17)	0.0190 (19)	−0.0018 (14)	0.0085 (15)	−0.0029 (15)
C2F	0.028 (2)	0.022 (2)	0.018 (2)	0.0001 (16)	0.0041 (17)	−0.0037 (17)
N3F	0.0274 (18)	0.0210 (17)	0.0181 (18)	−0.0014 (13)	0.0046 (14)	−0.0041 (15)
C4F	0.032 (2)	0.023 (2)	0.017 (2)	0.0006 (17)	0.0021 (17)	−0.0040 (18)
C5F	0.040 (2)	0.017 (2)	0.027 (2)	−0.0010 (17)	0.0033 (19)	−0.0056 (18)
C6F	0.039 (2)	0.027 (2)	0.024 (2)	−0.0061 (18)	0.0114 (19)	−0.0088 (19)
O21F	0.0417 (17)	0.0164 (14)	0.0290 (17)	−0.0050 (12)	0.0094 (13)	−0.0061 (12)
N41F	0.046 (2)	0.0194 (17)	0.022 (2)	−0.0082 (15)	0.0149 (16)	−0.0057 (16)
F51F	0.0744 (18)	0.0215 (12)	0.0372 (16)	−0.0122 (12)	0.0260 (13)	−0.0139 (12)
N1G	0.0346 (19)	0.0182 (16)	0.0198 (18)	−0.0028 (14)	0.0087 (15)	−0.0070 (15)
C2G	0.027 (2)	0.0138 (18)	0.020 (2)	−0.0015 (15)	0.0029 (17)	−0.0047 (17)
N3G	0.0321 (19)	0.0141 (17)	0.024 (2)	−0.0023 (13)	0.0091 (15)	−0.0068 (15)
C4G	0.027 (2)	0.023 (2)	0.026 (2)	0.0008 (16)	0.0057 (17)	−0.0121 (18)
C5G	0.033 (2)	0.020 (2)	0.024 (2)	−0.0037 (17)	0.0160 (18)	−0.0070 (18)
C6G	0.028 (2)	0.022 (2)	0.023 (2)	0.0034 (16)	0.0007 (17)	−0.0077 (18)
N21G	0.040 (2)	0.0117 (16)	0.0214 (19)	−0.0037 (14)	0.0116 (15)	−0.0055 (15)
O41G	0.0398 (16)	0.0171 (14)	0.0337 (17)	−0.0052 (12)	0.0138 (13)	−0.0122 (13)
N61G	0.053 (2)	0.0216 (18)	0.028 (2)	−0.0057 (16)	0.0173 (18)	−0.0042 (17)
N1H	0.0348 (19)	0.0156 (16)	0.0190 (18)	0.0004 (14)	0.0077 (15)	−0.0068 (14)
C2H	0.024 (2)	0.0154 (19)	0.017 (2)	−0.0026 (15)	0.0023 (16)	−0.0015 (16)
N3H	0.0270 (17)	0.0166 (16)	0.0189 (18)	−0.0033 (13)	0.0045 (14)	−0.0063 (14)
C4H	0.026 (2)	0.0174 (19)	0.027 (2)	−0.0021 (16)	0.0008 (17)	−0.0079 (18)
C5H	0.038 (2)	0.0098 (18)	0.028 (2)	−0.0028 (16)	0.0058 (19)	−0.0037 (17)
C6H	0.032 (2)	0.0155 (19)	0.020 (2)	−0.0018 (16)	0.0058 (17)	0.0006 (17)
O21H	0.0391 (16)	0.0155 (13)	0.0270 (16)	0.0002 (11)	0.0099 (13)	−0.0092 (12)
N41H	0.0366 (19)	0.0152 (16)	0.027 (2)	−0.0010 (14)	0.0115 (15)	−0.0085 (15)
F51H	0.0547 (15)	0.0133 (11)	0.0390 (15)	−0.0044 (10)	0.0133 (12)	−0.0071 (11)
N1I	0.0324 (19)	0.0233 (18)	0.0176 (18)	−0.0019 (14)	0.0090 (15)	−0.0042 (15)
C2I	0.027 (2)	0.020 (2)	0.019 (2)	−0.0024 (16)	0.0026 (17)	−0.0070 (17)
N3I	0.0297 (17)	0.0139 (15)	0.0159 (17)	−0.0030 (13)	0.0020 (14)	−0.0024 (13)
C4I	0.029 (2)	0.021 (2)	0.018 (2)	−0.0001 (16)	−0.0025 (17)	−0.0054 (17)
C5I	0.032 (2)	0.0182 (19)	0.027 (2)	0.0027 (16)	−0.0008 (18)	−0.0091 (18)
C6I	0.029 (2)	0.024 (2)	0.020 (2)	0.0008 (16)	0.0055 (17)	−0.0115 (18)
O21I	0.0397 (16)	0.0162 (14)	0.0291 (16)	−0.0038 (11)	0.0134 (13)	−0.0063 (12)
N41I	0.039 (2)	0.0183 (16)	0.026 (2)	0.0000 (14)	0.0075 (16)	−0.0040 (15)
F51I	0.0510 (15)	0.0141 (11)	0.0365 (14)	0.0005 (10)	0.0033 (11)	−0.0103 (10)
O1Y	0.0524 (19)	0.0497 (19)	0.0308 (18)	−0.0039 (15)	0.0143 (15)	−0.0198 (16)
C2Y	0.034 (2)	0.033 (2)	0.035 (3)	0.0021 (19)	−0.002 (2)	−0.020 (2)
N3Y	0.0326 (18)	0.0295 (17)	0.0202 (18)	−0.0048 (14)	0.0056 (15)	−0.0109 (15)
C5Y	0.044 (3)	0.033 (2)	0.041 (3)	−0.0074 (19)	0.005 (2)	−0.021 (2)
C4Y	0.048 (3)	0.055 (3)	0.034 (3)	−0.012 (2)	0.010 (2)	−0.016 (2)
O1Z	0.067 (2)	0.0376 (18)	0.0363 (19)	−0.0056 (15)	0.0215 (16)	−0.0189 (16)
C2Z	0.063 (3)	0.028 (2)	0.035 (3)	−0.011 (2)	0.020 (2)	−0.008 (2)
N3Z	0.042 (2)	0.0276 (18)	0.0223 (19)	−0.0067 (15)	0.0115 (16)	−0.0088 (16)
C4Z	0.053 (3)	0.047 (3)	0.033 (3)	0.004 (2)	−0.001 (2)	−0.018 (2)
C5Z	0.071 (4)	0.033 (3)	0.060 (4)	−0.015 (2)	0.025 (3)	−0.009 (3)

Geometric parameters (Å, º)

N1A—C2A	1.328 (5)	C4E—N41E	1.347 (5)
N1A—C6A	1.365 (5)	C4E—C5E	1.414 (6)
C2A—N21A	1.340 (5)	C5E—C6E	1.354 (6)
C2A—N3A	1.378 (5)	C5E—F51E	1.367 (4)
N3A—C4A	1.395 (5)	C6E—H6E	0.9500
N3A—H3A	0.87 (4)	N41E—H41E	0.889 (19)
C4A—O41A	1.272 (4)	N41E—H41F	0.893 (19)
C4A—C5A	1.391 (6)	N1F—C6F	1.357 (5)
C5A—C6A	1.407 (5)	N1F—C2F	1.385 (5)
C5A—H5A	0.9500	N1F—H1F	0.889 (19)
C6A—N61A	1.347 (5)	C2F—O21F	1.260 (4)
N21A—H21A	0.865 (19)	C2F—N3F	1.373 (5)
N21A—H21B	0.880 (19)	N3F—C4F	1.338 (5)
N61A—H61A	0.868 (19)	C4F—N41F	1.337 (5)
N61A—H61B	0.890 (19)	C4F—C5F	1.423 (5)
N1B—C6B	1.361 (5)	C5F—C6F	1.340 (6)
N1B—C2B	1.376 (5)	C5F—F51F	1.364 (4)
N1B—H1B	0.873 (19)	C6F—H6F	0.9500
C2B—O21B	1.260 (4)	N41F—H41G	0.882 (19)
C2B—N3B	1.378 (5)	N41F—H41H	0.877 (19)
N3B—C4B	1.343 (5)	N1G—C2G	1.330 (5)
C4B—N41B	1.323 (5)	N1G—C6G	1.368 (5)
C4B—C5B	1.436 (6)	C2G—N21G	1.343 (5)
C5B—C6B	1.329 (5)	C2G—N3G	1.371 (4)
C5B—F51B	1.367 (4)	N3G—C4G	1.398 (5)
C6B—H6B	0.9500	N3G—H3G	0.876 (19)
N41B—H41A	0.892 (19)	C4G—O41G	1.266 (4)
N41B—H41B	0.862 (19)	C4G—C5G	1.392 (5)
N1C—C6C	1.355 (5)	C5G—C6G	1.412 (5)
N1C—C2C	1.384 (5)	C5G—H5G	0.9500
N1C—H1C	0.86 (5)	C6G—N61G	1.349 (5)
C2C—O21C	1.256 (4)	N21G—H21E	0.91 (5)
C2C—N3C	1.364 (5)	N21G—H21F	0.88 (4)
N3C—C4C	1.354 (5)	N61G—H61E	0.85 (4)
C4C—N41C	1.328 (5)	N61G—H61F	0.89 (5)
C4C—C5C	1.429 (5)	N1H—C6H	1.355 (5)
C5C—C6C	1.333 (6)	N1H—C2H	1.377 (5)
C5C—F51C	1.358 (4)	N1H—H1H	0.870 (19)
C6C—H6C	0.9500	C2H—O21H	1.268 (4)
N41C—H41C	0.883 (19)	C2H—N3H	1.355 (4)
N41C—H41D	0.893 (19)	N3H—C4H	1.364 (4)
O1X—C2X	1.209 (5)	C4H—N41H	1.337 (5)
O1X—C2X'	1.264 (9)	C4H—C5H	1.412 (6)
N3X—C2X'	1.287 (9)	C5H—C6H	1.332 (5)
N3X—C2X	1.374 (6)	C5H—F51H	1.382 (4)
N3X—C4X	1.405 (6)	C6H—H6H	0.9500
N3X—C5X	1.473 (6)	N41H—H41I	0.896 (19)
N3X—C4X'	1.480 (9)	N41H—H41J	0.885 (19)
N3X—C5X'	1.486 (9)	N1I—C6I	1.361 (5)
C2X—H2X1	0.9500	N1I—C2I	1.381 (5)
C4X—H4X1	0.9800	N1I—H1I	0.868 (19)
C4X—H4X2	0.9800	C2I—O21I	1.250 (4)
C4X—H4X3	0.9800	C2I—N3I	1.363 (5)
C5X—H5X1	0.9800	N3I—C4I	1.346 (4)
C5X—H5X2	0.9800	C4I—N41I	1.345 (5)
C5X—H5X3	0.9800	C4I—C5I	1.419 (5)
C2X'—H2X2	0.9500	C5I—C6I	1.325 (6)
C4X'—H4X4	0.9800	C5I—F51I	1.379 (4)
C4X'—H4X5	0.9800	C6I—H6I	0.9500
C4X'—H4X6	0.9800	N41I—H41K	0.880 (18)
C5X'—H5X4	0.9800	N41I—H41L	0.904 (19)
C5X'—H5X5	0.9800	O1Y—C2Y	1.211 (5)
C5X'—H5X6	0.9800	C2Y—N3Y	1.344 (4)
N1D—C2D	1.344 (5)	C2Y—H2Y	0.9500
N1D—C6D	1.375 (4)	N3Y—C5Y	1.456 (5)
C2D—N21D	1.339 (5)	N3Y—C4Y	1.459 (6)
C2D—N3D	1.360 (4)	C5Y—H5Y1	0.9800
N3D—C4D	1.392 (5)	C5Y—H5Y2	0.9800
N3D—H3D	0.903 (19)	C5Y—H5Y3	0.9800
C4D—O41D	1.277 (4)	C4Y—H4Y1	0.9800
C4D—C5D	1.403 (6)	C4Y—H4Y2	0.9800
C5D—C6D	1.392 (5)	C4Y—H4Y3	0.9800
C5D—H5D	0.9500	O1Z—C2Z	1.247 (5)
C6D—N61D	1.362 (5)	C2Z—N3Z	1.321 (5)
N21D—H21C	0.87 (5)	C2Z—H2Z	0.9500
N21D—H21D	0.88 (4)	N3Z—C5Z	1.444 (6)
N61D—H61C	0.897 (18)	N3Z—C4Z	1.450 (5)
N61D—H61D	0.902 (19)	C4Z—H4Z1	0.9800
N1E—C6E	1.358 (5)	C4Z—H4Z2	0.9800
N1E—C2E	1.376 (5)	C4Z—H4Z3	0.9800
N1E—H1E	0.882 (19)	C5Z—H5Z1	0.9800
C2E—O21E	1.263 (4)	C5Z—H5Z2	0.9800
C2E—N3E	1.371 (5)	C5Z—H5Z3	0.9800
N3E—C4E	1.342 (5)
C2A—N1A—C6A	117.2 (3)	O21E—C2E—N3E	121.3 (4)
N1A—C2A—N21A	120.4 (3)	O21E—C2E—N1E	119.1 (3)
N1A—C2A—N3A	122.6 (3)	N3E—C2E—N1E	119.6 (3)
N21A—C2A—N3A	116.9 (4)	C4E—N3E—C2E	119.2 (4)
C2A—N3A—C4A	121.6 (4)	N3E—C4E—N41E	118.8 (4)
C2A—N3A—H3A	120 (3)	N3E—C4E—C5E	120.7 (3)
C4A—N3A—H3A	119 (3)	N41E—C4E—C5E	120.5 (3)
O41A—C4A—C5A	126.6 (3)	C6E—C5E—F51E	121.4 (4)
O41A—C4A—N3A	117.0 (4)	C6E—C5E—C4E	120.1 (3)
C5A—C4A—N3A	116.3 (3)	F51E—C5E—C4E	118.5 (3)
C4A—C5A—C6A	119.2 (4)	C5E—C6E—N1E	118.2 (4)
C4A—C5A—H5A	120.4	C5E—C6E—H6E	120.9
C6A—C5A—H5A	120.4	N1E—C6E—H6E	120.9
N61A—C6A—N1A	114.7 (3)	C4E—N41E—H41E	119 (3)
N61A—C6A—C5A	122.4 (4)	C4E—N41E—H41F	120 (3)
N1A—C6A—C5A	122.9 (4)	H41E—N41E—H41F	119 (4)
C2A—N21A—H21A	117 (3)	C6F—N1F—C2F	121.5 (4)
C2A—N21A—H21B	124 (3)	C6F—N1F—H1F	118 (3)
H21A—N21A—H21B	119 (4)	C2F—N1F—H1F	121 (3)
C6A—N61A—H61A	121 (3)	O21F—C2F—N3F	121.0 (3)
C6A—N61A—H61B	125 (3)	O21F—C2F—N1F	119.4 (4)
H61A—N61A—H61B	114 (4)	N3F—C2F—N1F	119.5 (3)
C6B—N1B—C2B	122.2 (3)	C4F—N3F—C2F	119.7 (3)
C6B—N1B—H1B	122 (3)	N41F—C4F—N3F	119.7 (3)
C2B—N1B—H1B	116 (3)	N41F—C4F—C5F	120.4 (3)
O21B—C2B—N1B	118.8 (3)	N3F—C4F—C5F	119.9 (4)
O21B—C2B—N3B	121.8 (4)	C6F—C5F—F51F	120.8 (4)
N1B—C2B—N3B	119.4 (3)	C6F—C5F—C4F	120.5 (3)
C4B—N3B—C2B	119.5 (4)	F51F—C5F—C4F	118.7 (4)
N41B—C4B—N3B	118.9 (4)	C5F—C6F—N1F	118.9 (4)
N41B—C4B—C5B	121.6 (3)	C5F—C6F—H6F	120.6
N3B—C4B—C5B	119.5 (3)	N1F—C6F—H6F	120.6
C6B—C5B—F51B	122.6 (4)	C4F—N41F—H41G	125 (3)
C6B—C5B—C4B	120.8 (3)	C4F—N41F—H41H	115 (3)
F51B—C5B—C4B	116.6 (3)	H41G—N41F—H41H	118 (4)
C5B—C6B—N1B	118.5 (4)	C2G—N1G—C6G	117.1 (3)
C5B—C6B—H6B	120.7	N1G—C2G—N21G	120.0 (3)
N1B—C6B—H6B	120.7	N1G—C2G—N3G	122.6 (3)
C4B—N41B—H41A	124 (3)	N21G—C2G—N3G	117.4 (4)
C4B—N41B—H41B	124 (3)	C2G—N3G—C4G	122.3 (3)
H41A—N41B—H41B	112 (4)	C2G—N3G—H3G	118 (2)
C6C—N1C—C2C	121.3 (4)	C4G—N3G—H3G	118 (3)
C6C—N1C—H1C	116 (3)	O41G—C4G—C5G	127.3 (3)
C2C—N1C—H1C	122 (3)	O41G—C4G—N3G	116.8 (4)
O21C—C2C—N3C	121.1 (3)	C5G—C4G—N3G	115.8 (3)
O21C—C2C—N1C	119.6 (4)	C4G—C5G—C6G	119.4 (3)
N3C—C2C—N1C	119.3 (3)	C4G—C5G—H5G	120.3
C4C—N3C—C2C	120.4 (3)	C6G—C5G—H5G	120.3
N41C—C4C—N3C	119.6 (4)	N61G—C6G—N1G	114.6 (3)
N41C—C4C—C5C	121.6 (3)	N61G—C6G—C5G	122.6 (4)
N3C—C4C—C5C	118.9 (4)	N1G—C6G—C5G	122.8 (4)
C6C—C5C—F51C	121.0 (4)	C2G—N21G—H21E	116 (2)
C6C—C5C—C4C	120.3 (3)	C2G—N21G—H21F	115 (3)
F51C—C5C—C4C	118.6 (4)	H21E—N21G—H21F	125 (4)
C5C—C6C—N1C	119.7 (4)	C6G—N61G—H61E	122 (3)
C5C—C6C—H6C	120.1	C6G—N61G—H61F	120 (3)
N1C—C6C—H6C	120.1	H61E—N61G—H61F	118 (5)
C4C—N41C—H41C	118 (3)	C6H—N1H—C2H	121.3 (3)
C4C—N41C—H41D	115 (3)	C6H—N1H—H1H	120 (3)
H41C—N41C—H41D	126 (4)	C2H—N1H—H1H	118 (3)
C2X—O1X—C2X'	56.5 (6)	O21H—C2H—N3H	121.1 (3)
C2X'—N3X—C2X	52.1 (7)	O21H—C2H—N1H	118.9 (3)
C2X'—N3X—C4X	173.7 (10)	N3H—C2H—N1H	120.0 (3)
C2X—N3X—C4X	122.5 (5)	C2H—N3H—C4H	119.4 (3)
C2X'—N3X—C5X	65.5 (6)	N41H—C4H—N3H	118.0 (4)
C2X—N3X—C5X	117.5 (4)	N41H—C4H—C5H	122.9 (3)
C4X—N3X—C5X	119.9 (4)	N3H—C4H—C5H	119.1 (3)
C2X'—N3X—C4X'	127.4 (11)	C6H—C5H—F51H	122.0 (4)
C2X—N3X—C4X'	179.4 (11)	C6H—C5H—C4H	120.9 (3)
C4X—N3X—C4X'	57.9 (9)	F51H—C5H—C4H	117.1 (3)
C5X—N3X—C4X'	62.0 (9)	C5H—C6H—N1H	119.0 (4)
C2X'—N3X—C5X'	124.7 (9)	C5H—C6H—H6H	120.5
C2X—N3X—C5X'	72.6 (7)	N1H—C6H—H6H	120.5
C4X—N3X—C5X'	50.2 (7)	C4H—N41H—H41I	121 (2)
C5X—N3X—C5X'	168.6 (7)	C4H—N41H—H41J	116 (3)
C4X'—N3X—C5X'	107.9 (10)	H41I—N41H—H41J	122 (4)
O1X—C2X—N3X	124.2 (5)	C6I—N1I—C2I	121.1 (4)
O1X—C2X—H2X1	117.9	C6I—N1I—H1I	113 (3)
N3X—C2X—H2X1	117.9	C2I—N1I—H1I	126 (3)
N3X—C4X—H4X1	109.5	O21I—C2I—N3I	121.0 (3)
N3X—C4X—H4X2	109.5	O21I—C2I—N1I	119.7 (4)
H4X1—C4X—H4X2	109.5	N3I—C2I—N1I	119.3 (3)
N3X—C4X—H4X3	109.5	C4I—N3I—C2I	120.3 (3)
H4X1—C4X—H4X3	109.5	N3I—C4I—N41I	118.6 (3)
H4X2—C4X—H4X3	109.5	N3I—C4I—C5I	119.2 (4)
N3X—C5X—H5X1	109.5	N41I—C4I—C5I	122.3 (3)
N3X—C5X—H5X2	109.5	C6I—C5I—F51I	121.2 (3)
H5X1—C5X—H5X2	109.5	C6I—C5I—C4I	120.7 (3)
N3X—C5X—H5X3	109.5	F51I—C5I—C4I	118.0 (4)
H5X1—C5X—H5X3	109.5	C5I—C6I—N1I	119.4 (3)
H5X2—C5X—H5X3	109.5	C5I—C6I—H6I	120.3
O1X—C2X'—N3X	127.1 (12)	N1I—C6I—H6I	120.3
O1X—C2X'—H2X2	116.4	C4I—N41I—H41K	122 (3)
N3X—C2X'—H2X2	116.4	C4I—N41I—H41L	119 (3)
N3X—C4X'—H4X4	109.5	H41K—N41I—H41L	118 (4)
N3X—C4X'—H4X5	109.5	O1Y—C2Y—N3Y	125.8 (4)
H4X4—C4X'—H4X5	109.5	O1Y—C2Y—H2Y	117.1
N3X—C4X'—H4X6	109.5	N3Y—C2Y—H2Y	117.1
H4X4—C4X'—H4X6	109.5	C2Y—N3Y—C5Y	121.7 (4)
H4X5—C4X'—H4X6	109.5	C2Y—N3Y—C4Y	120.5 (4)
N3X—C5X'—H5X4	109.5	C5Y—N3Y—C4Y	117.8 (3)
N3X—C5X'—H5X5	109.5	N3Y—C5Y—H5Y1	109.5
H5X4—C5X'—H5X5	109.5	N3Y—C5Y—H5Y2	109.5
N3X—C5X'—H5X6	109.5	H5Y1—C5Y—H5Y2	109.5
H5X4—C5X'—H5X6	109.5	N3Y—C5Y—H5Y3	109.5
H5X5—C5X'—H5X6	109.5	H5Y1—C5Y—H5Y3	109.5
C2D—N1D—C6D	116.0 (3)	H5Y2—C5Y—H5Y3	109.5
N21D—C2D—N1D	119.5 (3)	N3Y—C4Y—H4Y1	109.5
N21D—C2D—N3D	118.1 (4)	N3Y—C4Y—H4Y2	109.5
N1D—C2D—N3D	122.4 (3)	H4Y1—C4Y—H4Y2	109.5
C2D—N3D—C4D	122.7 (4)	N3Y—C4Y—H4Y3	109.5
C2D—N3D—H3D	115 (2)	H4Y1—C4Y—H4Y3	109.5
C4D—N3D—H3D	121 (2)	H4Y2—C4Y—H4Y3	109.5
O41D—C4D—N3D	116.9 (4)	O1Z—C2Z—N3Z	125.9 (5)
O41D—C4D—C5D	126.7 (3)	O1Z—C2Z—H2Z	117.0
N3D—C4D—C5D	116.3 (3)	N3Z—C2Z—H2Z	117.0
C6D—C5D—C4D	118.1 (3)	C2Z—N3Z—C5Z	121.1 (4)
C6D—C5D—H5D	120.9	C2Z—N3Z—C4Z	121.8 (4)
C4D—C5D—H5D	120.9	C5Z—N3Z—C4Z	117.1 (3)
N61D—C6D—N1D	114.6 (3)	N3Z—C4Z—H4Z1	109.5
N61D—C6D—C5D	121.0 (3)	N3Z—C4Z—H4Z2	109.5
N1D—C6D—C5D	124.3 (4)	H4Z1—C4Z—H4Z2	109.5
C2D—N21D—H21C	119 (2)	N3Z—C4Z—H4Z3	109.5
C2D—N21D—H21D	122 (3)	H4Z1—C4Z—H4Z3	109.5
H21C—N21D—H21D	117 (4)	H4Z2—C4Z—H4Z3	109.5
C6D—N61D—H61C	112 (3)	N3Z—C5Z—H5Z1	109.5
C6D—N61D—H61D	120 (3)	N3Z—C5Z—H5Z2	109.5
H61C—N61D—H61D	123 (4)	H5Z1—C5Z—H5Z2	109.5
C6E—N1E—C2E	122.3 (3)	N3Z—C5Z—H5Z3	109.5
C6E—N1E—H1E	121 (3)	H5Z1—C5Z—H5Z3	109.5
C2E—N1E—H1E	116 (3)	H5Z2—C5Z—H5Z3	109.5
C6A—N1A—C2A—N21A	179.2 (3)	C2E—N3E—C4E—N41E	−179.5 (4)
C6A—N1A—C2A—N3A	2.2 (5)	C2E—N3E—C4E—C5E	−0.4 (6)
N1A—C2A—N3A—C4A	−2.9 (6)	N3E—C4E—C5E—C6E	−0.8 (6)
N21A—C2A—N3A—C4A	−180.0 (4)	N41E—C4E—C5E—C6E	178.3 (4)
C2A—N3A—C4A—O41A	178.7 (3)	N3E—C4E—C5E—F51E	−178.8 (3)
C2A—N3A—C4A—C5A	0.5 (6)	N41E—C4E—C5E—F51E	0.3 (6)
O41A—C4A—C5A—C6A	−175.7 (4)	F51E—C5E—C6E—N1E	178.9 (4)
N3A—C4A—C5A—C6A	2.2 (6)	C4E—C5E—C6E—N1E	0.9 (6)
C2A—N1A—C6A—N61A	−177.2 (4)	C2E—N1E—C6E—C5E	0.1 (6)
C2A—N1A—C6A—C5A	0.7 (6)	C6F—N1F—C2F—O21F	179.5 (4)
C4A—C5A—C6A—N61A	174.8 (4)	C6F—N1F—C2F—N3F	−0.2 (6)
C4A—C5A—C6A—N1A	−3.0 (6)	O21F—C2F—N3F—C4F	179.3 (4)
C6B—N1B—C2B—O21B	−178.5 (4)	N1F—C2F—N3F—C4F	−1.0 (5)
C6B—N1B—C2B—N3B	2.1 (6)	C2F—N3F—C4F—N41F	−177.2 (4)
O21B—C2B—N3B—C4B	178.3 (4)	C2F—N3F—C4F—C5F	2.0 (5)
N1B—C2B—N3B—C4B	−2.3 (5)	N41F—C4F—C5F—C6F	177.3 (4)
C2B—N3B—C4B—N41B	−179.8 (4)	N3F—C4F—C5F—C6F	−1.9 (6)
C2B—N3B—C4B—C5B	1.1 (5)	N41F—C4F—C5F—F51F	−3.2 (6)
N41B—C4B—C5B—C6B	−178.7 (4)	N3F—C4F—C5F—F51F	177.6 (3)
N3B—C4B—C5B—C6B	0.3 (6)	F51F—C5F—C6F—N1F	−178.8 (4)
N41B—C4B—C5B—F51B	1.0 (6)	C4F—C5F—C6F—N1F	0.7 (6)
N3B—C4B—C5B—F51B	−180.0 (3)	C2F—N1F—C6F—C5F	0.3 (6)
F51B—C5B—C6B—N1B	179.7 (4)	C6G—N1G—C2G—N21G	−179.6 (3)
C4B—C5B—C6B—N1B	−0.6 (6)	C6G—N1G—C2G—N3G	0.7 (5)
C2B—N1B—C6B—C5B	−0.6 (6)	N1G—C2G—N3G—C4G	0.2 (6)
C6C—N1C—C2C—O21C	−178.0 (4)	N21G—C2G—N3G—C4G	−179.6 (3)
C6C—N1C—C2C—N3C	1.4 (6)	C2G—N3G—C4G—O41G	178.4 (3)
O21C—C2C—N3C—C4C	179.0 (4)	C2G—N3G—C4G—C5G	−1.7 (5)
N1C—C2C—N3C—C4C	−0.4 (6)	O41G—C4G—C5G—C6G	−177.7 (4)
C2C—N3C—C4C—N41C	178.3 (4)	N3G—C4G—C5G—C6G	2.3 (6)
C2C—N3C—C4C—C5C	−1.7 (5)	C2G—N1G—C6G—N61G	−177.7 (4)
N41C—C4C—C5C—C6C	−177.1 (4)	C2G—N1G—C6G—C5G	0.1 (5)
N3C—C4C—C5C—C6C	2.9 (6)	C4G—C5G—C6G—N61G	176.0 (4)
N41C—C4C—C5C—F51C	0.4 (6)	C4G—C5G—C6G—N1G	−1.6 (6)
N3C—C4C—C5C—F51C	−179.6 (3)	C6H—N1H—C2H—O21H	−175.6 (3)
F51C—C5C—C6C—N1C	−179.4 (4)	C6H—N1H—C2H—N3H	5.9 (5)
C4C—C5C—C6C—N1C	−1.9 (6)	O21H—C2H—N3H—C4H	176.3 (3)
C2C—N1C—C6C—C5C	−0.2 (6)	N1H—C2H—N3H—C4H	−5.2 (5)
C2X'—O1X—C2X—N3X	1.7 (17)	C2H—N3H—C4H—N41H	179.3 (3)
C2X'—N3X—C2X—O1X	−1.7 (17)	C2H—N3H—C4H—C5H	0.6 (5)
C4X—N3X—C2X—O1X	−177.6 (5)	N41H—C4H—C5H—C6H	−174.9 (4)
C5X—N3X—C2X—O1X	2.7 (7)	N3H—C4H—C5H—C6H	3.7 (6)
C5X'—N3X—C2X—O1X	177.0 (10)	N41H—C4H—C5H—F51H	3.3 (6)
C2X—O1X—C2X'—N3X	−1.9 (19)	N3H—C4H—C5H—F51H	−178.1 (3)
C2X—N3X—C2X'—O1X	1.7 (17)	F51H—C5H—C6H—N1H	178.7 (3)
C5X—N3X—C2X'—O1X	−174 (3)	C4H—C5H—C6H—N1H	−3.2 (6)
C4X'—N3X—C2X'—O1X	−179 (2)	C2H—N1H—C6H—C5H	−1.5 (6)
C5X'—N3X—C2X'—O1X	0 (4)	C6I—N1I—C2I—O21I	−179.9 (3)
C6D—N1D—C2D—N21D	−178.4 (3)	C6I—N1I—C2I—N3I	1.7 (5)
C6D—N1D—C2D—N3D	1.8 (5)	O21I—C2I—N3I—C4I	−179.0 (3)
N21D—C2D—N3D—C4D	179.8 (4)	N1I—C2I—N3I—C4I	−0.7 (5)
N1D—C2D—N3D—C4D	−0.4 (6)	C2I—N3I—C4I—N41I	179.2 (3)
C2D—N3D—C4D—O41D	−178.7 (4)	C2I—N3I—C4I—C5I	−1.3 (5)
C2D—N3D—C4D—C5D	0.8 (5)	N3I—C4I—C5I—C6I	2.6 (6)
O41D—C4D—C5D—C6D	176.8 (4)	N41I—C4I—C5I—C6I	−178.0 (4)
N3D—C4D—C5D—C6D	−2.6 (5)	N3I—C4I—C5I—F51I	−177.4 (3)
C2D—N1D—C6D—N61D	177.0 (3)	N41I—C4I—C5I—F51I	2.1 (6)
C2D—N1D—C6D—C5D	−3.8 (5)	F51I—C5I—C6I—N1I	178.3 (3)
C4D—C5D—C6D—N61D	−176.6 (4)	C4I—C5I—C6I—N1I	−1.6 (6)
C4D—C5D—C6D—N1D	4.3 (6)	C2I—N1I—C6I—C5I	−0.5 (6)
C6E—N1E—C2E—O21E	178.9 (4)	O1Y—C2Y—N3Y—C5Y	−1.3 (6)
C6E—N1E—C2E—N3E	−1.3 (6)	O1Y—C2Y—N3Y—C4Y	178.7 (4)
O21E—C2E—N3E—C4E	−178.7 (4)	O1Z—C2Z—N3Z—C5Z	2.4 (8)
N1E—C2E—N3E—C4E	1.4 (5)	O1Z—C2Z—N3Z—C4Z	179.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···N3B	0.87 (4)	2.02 (5)	2.894 (5)	178 (4)
N21A—H21A···N1A^i	0.87 (2)	2.11 (2)	2.977 (4)	178 (4)
N21A—H21B···O21B	0.88 (2)	2.03 (2)	2.909 (5)	178 (4)
N61A—H61B···O1X	0.89 (2)	2.02 (2)	2.884 (5)	164 (4)
N1B—H1B···N3C	0.87 (2)	1.94 (2)	2.815 (4)	177 (4)
N41B—H41A···O41A	0.89 (2)	1.99 (2)	2.878 (5)	174 (4)
N41B—H41B···O41A^ii	0.86 (2)	2.05 (3)	2.860 (4)	156 (4)
N1C—H1C···O21C^iii	0.86 (5)	1.92 (5)	2.780 (5)	178 (4)
N41C—H41D···O21B	0.89 (2)	2.13 (2)	3.010 (4)	167 (4)
N41C—H41C···O1X^i	0.88 (2)	2.25 (2)	3.094 (4)	160 (4)
N3D—H3D···N3E	0.90 (2)	2.00 (2)	2.898 (5)	177 (4)
N21D—H21D···N1G^iv	0.88 (4)	2.13 (4)	2.996 (4)	173 (4)
N21D—H21C···O21E	0.87 (5)	2.05 (5)	2.903 (5)	167 (4)
N61D—H61D···O1Y	0.90 (2)	2.01 (2)	2.885 (4)	163 (4)
N1E—H1E···N3F	0.88 (2)	1.93 (2)	2.801 (4)	172 (4)
N41E—H41F···O41D	0.89 (2)	1.97 (2)	2.861 (5)	175 (4)
N41E—H41E···O41G^v	0.89 (2)	2.08 (3)	2.895 (4)	151 (4)
N1F—H1F···O21I	0.89 (2)	1.89 (2)	2.768 (4)	168 (4)
N41F—H41H···O21E	0.88 (2)	2.12 (2)	2.999 (4)	179 (4)
N41F—H41G···O1Z^iv	0.88 (2)	2.23 (2)	3.112 (4)	173 (4)
N3G—H3G···N3H	0.88 (2)	2.03 (2)	2.904 (5)	174 (4)
N21G—H21F···N1D^vi	0.88 (4)	2.09 (4)	2.968 (4)	176 (4)
N21G—H21E···O21H	0.91 (5)	2.03 (5)	2.933 (5)	171 (3)
N61G—H61F···O1Z	0.89 (5)	2.05 (5)	2.866 (5)	153 (4)
N1H—H1H···N3I	0.87 (2)	1.94 (2)	2.809 (4)	176 (4)
N41H—H41I···O41G	0.90 (2)	1.97 (2)	2.865 (5)	173 (4)
N41H—H41J···O41D^vii	0.89 (2)	2.09 (3)	2.847 (4)	143 (4)
N1I—H1I···O21F	0.87 (2)	1.90 (2)	2.762 (4)	173 (4)
N41I—H41L···O21H	0.90 (2)	2.07 (2)	2.974 (4)	174 (4)
N41I—H41K···O21H^viii	0.88 (2)	2.31 (3)	3.068 (4)	144 (3)

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

(VI)

Crystal data

C8H11N5O3	Z = 4
Mr = 225.22	F(000) = 472
Monoclinic, P21/c	Dx = 1.620 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.9182 (11) Å	Cell parameters from 3262 reflections
b = 11.1666 (8) Å	θ = 3.3–25.9°
c = 7.9786 (9) Å	µ = 0.13 mm^−1
β = 108.346 (8)°	T = 173 K
V = 923.30 (15) Å^3	0.20 × 0.10 × 0.10 mm

Data collection

STOE IPDS II two-circle- diffractometer	1215 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.132
Graphite monochromator	θmax = 25.6°, θmin = 3.3°
ω scans	h = −13→13
6501 measured reflections	k = −13→13
1723 independent reflections	l = −8→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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0711P)^2] where P = (Fo^2 + 2Fc^2)/3
1723 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.27 e Å^−3
3 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
N1	0.9389 (2)	0.62257 (19)	0.6574 (3)	0.0176 (5)
H1	0.989 (3)	0.565 (2)	0.717 (4)	0.021*
C2	0.8285 (3)	0.5945 (2)	0.5242 (4)	0.0171 (5)
N3	0.7498 (2)	0.6754 (2)	0.4241 (3)	0.0179 (5)
C4	0.7903 (3)	0.7886 (2)	0.4713 (4)	0.0167 (6)
C5	0.8981 (2)	0.8258 (2)	0.6046 (4)	0.0168 (5)
C6	0.9832 (3)	0.7382 (2)	0.7059 (4)	0.0168 (6)
N7	0.9048 (2)	0.95018 (19)	0.6117 (3)	0.0193 (5)
C8	0.8037 (3)	0.9860 (2)	0.4840 (4)	0.0182 (6)
H8	0.7831	1.0679	0.4568	0.022*
N9	0.7299 (2)	0.8920 (2)	0.3929 (3)	0.0180 (5)
N21	0.7989 (2)	0.4779 (2)	0.4990 (3)	0.0228 (5)
H21A	0.726 (2)	0.460 (3)	0.420 (4)	0.027*
H21B	0.851 (3)	0.422 (3)	0.561 (4)	0.027*
O61	1.08727 (19)	0.75473 (17)	0.8263 (3)	0.0237 (5)
C91	0.6116 (3)	0.8976 (2)	0.2434 (4)	0.0178 (5)
H91A	0.6242	0.9551	0.1557	0.021*
H91B	0.5951	0.8179	0.1865	0.021*
O92	0.50241 (18)	0.93261 (16)	0.2897 (3)	0.0193 (5)
C93	0.4725 (3)	0.8573 (2)	0.4169 (4)	0.0206 (6)
H93A	0.4084	0.8987	0.4609	0.025*
H93B	0.5517	0.8457	0.5185	0.025*
C94	0.4195 (3)	0.7356 (2)	0.3464 (4)	0.0200 (6)
H94A	0.4852	0.6915	0.3092	0.024*
H94B	0.4014	0.6892	0.4417	0.024*
O95	0.3043 (2)	0.74536 (19)	0.2006 (3)	0.0268 (5)
H95	0.2405	0.7501	0.2377	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0152 (11)	0.0138 (11)	0.0216 (12)	0.0001 (8)	0.0027 (9)	0.0005 (8)
C2	0.0160 (12)	0.0167 (12)	0.0202 (14)	0.0017 (10)	0.0080 (11)	−0.0019 (10)
N3	0.0189 (11)	0.0152 (11)	0.0190 (11)	−0.0006 (9)	0.0053 (9)	−0.0011 (8)
C4	0.0170 (12)	0.0173 (12)	0.0172 (13)	0.0011 (10)	0.0075 (11)	0.0025 (10)
C5	0.0153 (12)	0.0142 (12)	0.0203 (13)	−0.0038 (10)	0.0046 (11)	−0.0019 (10)
C6	0.0160 (13)	0.0156 (12)	0.0183 (14)	−0.0001 (9)	0.0047 (11)	0.0007 (9)
N7	0.0193 (11)	0.0130 (11)	0.0244 (12)	−0.0021 (9)	0.0051 (10)	−0.0007 (9)
C8	0.0184 (13)	0.0116 (11)	0.0248 (14)	−0.0006 (10)	0.0069 (11)	0.0014 (10)
N9	0.0194 (11)	0.0142 (10)	0.0198 (12)	0.0015 (9)	0.0055 (10)	0.0016 (8)
N21	0.0237 (12)	0.0136 (11)	0.0256 (13)	−0.0004 (10)	−0.0002 (10)	−0.0006 (9)
O61	0.0197 (10)	0.0190 (10)	0.0274 (11)	−0.0020 (7)	0.0000 (9)	0.0002 (8)
C91	0.0185 (12)	0.0181 (12)	0.0164 (13)	0.0019 (10)	0.0048 (11)	0.0026 (10)
O92	0.0176 (9)	0.0156 (9)	0.0234 (11)	0.0018 (7)	0.0047 (8)	0.0021 (7)
C93	0.0210 (13)	0.0230 (14)	0.0185 (14)	0.0003 (11)	0.0071 (11)	−0.0009 (10)
C94	0.0198 (13)	0.0193 (13)	0.0200 (14)	−0.0024 (10)	0.0049 (11)	0.0006 (10)
O95	0.0209 (10)	0.0308 (11)	0.0236 (11)	−0.0053 (9)	−0.0002 (9)	−0.0004 (8)

Geometric parameters (Å, º)

N1—C2	1.369 (4)	N9—C91	1.458 (3)
N1—C6	1.390 (3)	N21—H21A	0.864 (19)
N1—H1	0.885 (18)	N21—H21B	0.881 (19)
C2—N3	1.327 (4)	C91—O92	1.410 (3)
C2—N21	1.342 (4)	C91—H91A	0.9900
N3—C4	1.353 (4)	C91—H91B	0.9900
C4—N9	1.378 (3)	O92—C93	1.433 (3)
C4—C5	1.379 (4)	C93—C94	1.513 (4)
C5—N7	1.391 (4)	C93—H93A	0.9900
C5—C6	1.414 (4)	C93—H93B	0.9900
C6—O61	1.250 (3)	C94—O95	1.423 (3)
N7—C8	1.307 (4)	C94—H94A	0.9900
C8—N9	1.383 (4)	C94—H94B	0.9900
C8—H8	0.9500	O95—H95	0.8400
C2—N1—C6	124.9 (2)	C2—N21—H21A	117 (2)
C2—N1—H1	120 (2)	C2—N21—H21B	121 (2)
C6—N1—H1	115 (2)	H21A—N21—H21B	122 (3)
N3—C2—N21	119.4 (3)	O92—C91—N9	113.7 (2)
N3—C2—N1	123.8 (2)	O92—C91—H91A	108.8
N21—C2—N1	116.8 (2)	N9—C91—H91A	108.8
C2—N3—C4	112.0 (2)	O92—C91—H91B	108.8
N3—C4—N9	126.0 (2)	N9—C91—H91B	108.8
N3—C4—C5	128.4 (2)	H91A—C91—H91B	107.7
N9—C4—C5	105.6 (2)	C91—O92—C93	115.0 (2)
C4—C5—N7	110.7 (2)	O92—C93—C94	114.2 (2)
C4—C5—C6	118.7 (2)	O92—C93—H93A	108.7
N7—C5—C6	130.6 (3)	C94—C93—H93A	108.7
O61—C6—N1	120.2 (2)	O92—C93—H93B	108.7
O61—C6—C5	127.7 (2)	C94—C93—H93B	108.7
N1—C6—C5	112.0 (2)	H93A—C93—H93B	107.6
C8—N7—C5	104.7 (2)	O95—C94—C93	111.8 (2)
N7—C8—N9	112.8 (2)	O95—C94—H94A	109.3
N7—C8—H8	123.6	C93—C94—H94A	109.3
N9—C8—H8	123.6	O95—C94—H94B	109.3
C4—N9—C8	106.3 (2)	C93—C94—H94B	109.3
C4—N9—C91	125.6 (2)	H94A—C94—H94B	107.9
C8—N9—C91	128.1 (2)	C94—O95—H95	109.5
C6—N1—C2—N3	0.2 (4)	N7—C5—C6—N1	179.0 (3)
C6—N1—C2—N21	−178.3 (2)	C4—C5—N7—C8	−0.6 (3)
N21—C2—N3—C4	177.3 (2)	C6—C5—N7—C8	177.6 (3)
N1—C2—N3—C4	−1.2 (4)	C5—N7—C8—N9	0.2 (3)
C2—N3—C4—N9	179.9 (2)	N3—C4—N9—C8	179.5 (2)
C2—N3—C4—C5	−0.1 (4)	C5—C4—N9—C8	−0.5 (3)
N3—C4—C5—N7	−179.3 (2)	N3—C4—N9—C91	−0.6 (4)
N9—C4—C5—N7	0.7 (3)	C5—C4—N9—C91	179.4 (2)
N3—C4—C5—C6	2.3 (4)	N7—C8—N9—C4	0.2 (3)
N9—C4—C5—C6	−177.7 (2)	N7—C8—N9—C91	−179.7 (2)
C2—N1—C6—O61	−178.0 (3)	C4—N9—C91—O92	105.8 (3)
C2—N1—C6—C5	1.9 (4)	C8—N9—C91—O92	−74.3 (3)
C4—C5—C6—O61	177.0 (3)	N9—C91—O92—C93	−58.4 (3)
N7—C5—C6—O61	−1.1 (5)	C91—O92—C93—C94	−71.4 (3)
C4—C5—C6—N1	−2.9 (4)	O92—C93—C94—O95	−59.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7^i	0.89 (2)	1.96 (2)	2.834 (3)	169 (3)
N21—H21A···O95^ii	0.86 (2)	2.56 (3)	3.069 (3)	118 (3)
N21—H21B···O61^i	0.88 (2)	2.09 (2)	2.934 (3)	159 (3)
O95—H95···O61^iii	0.84	2.01	2.849 (3)	175

Symmetry codes: (i) −x+2, y−1/2, −z+3/2; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1, −y+3/2, z−1/2.

(VII) ;

Crystal data

C4H4FN3O·C8H11N5O3	F(000) = 736
Mr = 354.32	Dx = 1.622 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9824 reflections
a = 7.0859 (5) Å	θ = 3.6–26.0°
b = 9.0414 (5) Å	µ = 0.13 mm^−1
c = 22.8754 (16) Å	T = 173 K
β = 98.155 (6)°	Block, colourless
V = 1450.73 (16) Å^3	0.60 × 0.60 × 0.40 mm
Z = 4

Data collection

STOE IPDS II two-circle- diffractometer	2202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.073
Graphite monochromator	θmax = 25.7°, θmin = 3.5°
ω scans	h = −8→8
11519 measured reflections	k = −11→10
2718 independent reflections	l = −23→27

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0688P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
2718 reflections	Δρmax = 0.34 e Å^−3
252 parameters	Δρmin = −0.33 e Å^−3
2 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: 0.020 (3)

Special details

Experimental. ;

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	0.31615 (16)	0.63847 (13)	0.46492 (6)	0.0191 (3)
H1	0.282 (2)	0.5820 (19)	0.4938 (8)	0.028 (5)*
C2	0.38770 (19)	0.77873 (16)	0.47575 (6)	0.0193 (3)
N21	0.4025 (2)	0.82458 (17)	0.53167 (6)	0.0271 (3)
H21A	0.375 (3)	0.764 (2)	0.5596 (9)	0.033 (5)*
H21B	0.447 (3)	0.913 (2)	0.5402 (10)	0.039 (5)*
N3	0.43674 (16)	0.86735 (13)	0.43384 (5)	0.0192 (3)
C4	0.40557 (18)	0.80386 (16)	0.37951 (6)	0.0178 (3)
C5	0.33311 (19)	0.66518 (16)	0.36467 (6)	0.0186 (3)
C6	0.28091 (19)	0.57301 (15)	0.40952 (7)	0.0189 (3)
O61	0.20669 (15)	0.44856 (11)	0.40312 (5)	0.0262 (3)
N7	0.31657 (17)	0.64076 (14)	0.30431 (5)	0.0223 (3)
C8	0.3794 (2)	0.76291 (16)	0.28366 (7)	0.0216 (3)
H8	0.3851	0.7790	0.2429	0.026*
N9	0.43674 (16)	0.86634 (13)	0.32676 (5)	0.0185 (3)
C91	0.49976 (19)	1.01439 (16)	0.31408 (7)	0.0204 (3)
H91A	0.5635	1.0605	0.3509	0.025*
H91B	0.5934	1.0085	0.2859	0.025*
O92	0.34457 (14)	1.10231 (11)	0.28994 (4)	0.0217 (3)
C93	0.2348 (2)	1.15385 (18)	0.33420 (7)	0.0275 (4)
H93A	0.3109	1.2250	0.3607	0.033*
H93B	0.2010	1.0695	0.3583	0.033*
C94	0.0568 (2)	1.22747 (19)	0.30455 (8)	0.0319 (4)
H94A	−0.0162	1.1556	0.2776	0.038*
H94B	−0.0232	1.2551	0.3350	0.038*
O95	0.09130 (19)	1.35572 (13)	0.27195 (6)	0.0375 (3)
H95	0.1521	1.4178	0.2946	0.045*
N1'	0.20902 (18)	0.40773 (16)	0.65852 (6)	0.0267 (3)
H1'	0.232 (3)	0.437 (2)	0.6954 (11)	0.044 (6)*
C2'	0.2483 (2)	0.49881 (18)	0.61312 (7)	0.0237 (3)
O21'	0.31230 (16)	0.62467 (13)	0.62475 (5)	0.0300 (3)
N3'	0.21615 (17)	0.44579 (14)	0.55692 (6)	0.0231 (3)
C4'	0.14772 (19)	0.30924 (18)	0.54615 (7)	0.0235 (3)
N41'	0.1136 (2)	0.25984 (17)	0.49089 (6)	0.0293 (3)
H41A	0.138 (3)	0.319 (2)	0.4610 (9)	0.050 (6)*
H41B	0.068 (3)	0.169 (3)	0.4817 (10)	0.049 (6)*
C5'	0.1111 (2)	0.21774 (18)	0.59389 (8)	0.0258 (4)
F51'	0.04437 (15)	0.07822 (11)	0.58108 (5)	0.0387 (3)
C6'	0.1412 (2)	0.26770 (18)	0.64919 (7)	0.0268 (4)
H6'	0.1161	0.2073	0.6812	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0229 (6)	0.0170 (6)	0.0182 (6)	−0.0025 (5)	0.0052 (5)	0.0004 (5)
C2	0.0197 (6)	0.0177 (7)	0.0207 (8)	−0.0008 (5)	0.0033 (5)	−0.0028 (6)
N21	0.0425 (8)	0.0232 (7)	0.0165 (7)	−0.0116 (6)	0.0072 (6)	−0.0029 (6)
N3	0.0237 (6)	0.0170 (6)	0.0171 (6)	−0.0015 (5)	0.0030 (5)	−0.0009 (5)
C4	0.0163 (6)	0.0188 (7)	0.0185 (7)	0.0026 (5)	0.0034 (5)	−0.0001 (6)
C5	0.0190 (6)	0.0174 (7)	0.0195 (8)	0.0020 (5)	0.0026 (5)	−0.0023 (6)
C6	0.0186 (6)	0.0160 (7)	0.0220 (7)	0.0020 (5)	0.0023 (5)	−0.0028 (6)
O61	0.0361 (6)	0.0173 (6)	0.0258 (6)	−0.0060 (4)	0.0066 (4)	−0.0036 (4)
N7	0.0277 (6)	0.0205 (7)	0.0189 (7)	0.0022 (5)	0.0037 (5)	−0.0026 (5)
C8	0.0272 (7)	0.0221 (8)	0.0157 (7)	0.0046 (6)	0.0042 (6)	−0.0015 (6)
N9	0.0227 (6)	0.0168 (6)	0.0167 (6)	0.0016 (5)	0.0050 (5)	0.0008 (5)
C91	0.0217 (7)	0.0193 (7)	0.0211 (7)	0.0004 (5)	0.0059 (5)	0.0034 (6)
O92	0.0275 (5)	0.0205 (6)	0.0178 (5)	0.0051 (4)	0.0051 (4)	0.0010 (4)
C93	0.0326 (8)	0.0306 (9)	0.0201 (8)	0.0088 (7)	0.0072 (6)	−0.0048 (7)
C94	0.0302 (8)	0.0326 (9)	0.0319 (9)	0.0067 (7)	0.0016 (7)	−0.0087 (7)
O95	0.0519 (7)	0.0231 (6)	0.0332 (7)	0.0078 (5)	−0.0090 (5)	−0.0104 (5)
N1'	0.0263 (6)	0.0326 (8)	0.0215 (7)	0.0006 (5)	0.0048 (5)	0.0045 (6)
C2'	0.0208 (7)	0.0277 (8)	0.0233 (8)	0.0029 (6)	0.0052 (6)	0.0038 (6)
O21'	0.0367 (6)	0.0290 (6)	0.0252 (6)	−0.0039 (5)	0.0072 (5)	−0.0012 (5)
N3'	0.0239 (6)	0.0246 (7)	0.0215 (7)	0.0022 (5)	0.0054 (5)	0.0027 (5)
C4'	0.0184 (7)	0.0257 (8)	0.0268 (8)	0.0036 (6)	0.0051 (6)	0.0032 (6)
N41'	0.0373 (7)	0.0251 (8)	0.0261 (8)	−0.0046 (6)	0.0066 (6)	0.0006 (6)
C5'	0.0232 (7)	0.0223 (8)	0.0328 (9)	0.0004 (6)	0.0064 (6)	0.0051 (7)
F51'	0.0494 (6)	0.0270 (5)	0.0410 (6)	−0.0091 (4)	0.0112 (5)	0.0047 (4)
C6'	0.0217 (7)	0.0311 (9)	0.0283 (9)	0.0037 (6)	0.0062 (6)	0.0113 (7)

Geometric parameters (Å, º)

N1—C2	1.3751 (19)	C93—C94	1.500 (2)
N1—C6	1.3888 (19)	C93—H93A	0.9900
N1—H1	0.895 (15)	C93—H93B	0.9900
C2—N3	1.3328 (19)	C94—O95	1.419 (2)
C2—N21	1.335 (2)	C94—H94A	0.9900
N21—H21A	0.88 (2)	C94—H94B	0.9900
N21—H21B	0.87 (2)	O95—H95	0.8400
N3—C4	1.3583 (19)	N1'—C6'	1.360 (2)
C4—N9	1.3783 (19)	N1'—C2'	1.384 (2)
C4—C5	1.379 (2)	N1'—H1'	0.88 (2)
C5—N7	1.3866 (19)	C2'—O21'	1.240 (2)
C5—C6	1.411 (2)	C2'—N3'	1.361 (2)
C6—O61	1.2418 (18)	N3'—C4'	1.336 (2)
N7—C8	1.304 (2)	C4'—N41'	1.330 (2)
C8—N9	1.3775 (19)	C4'—C5'	1.423 (2)
C8—H8	0.9500	N41'—H41A	0.908 (16)
N9—C91	1.4533 (19)	N41'—H41B	0.90 (2)
C91—O92	1.4049 (17)	C5'—C6'	1.332 (2)
C91—H91A	0.9900	C5'—F51'	1.3643 (19)
C91—H91B	0.9900	C6'—H6'	0.9500
O92—C93	1.4393 (18)
C2—N1—C6	124.85 (13)	O92—C93—C94	109.22 (13)
C2—N1—H1	121.7 (12)	O92—C93—H93A	109.8
C6—N1—H1	113.4 (12)	C94—C93—H93A	109.8
N3—C2—N21	120.64 (14)	O92—C93—H93B	109.8
N3—C2—N1	123.50 (13)	C94—C93—H93B	109.8
N21—C2—N1	115.85 (14)	H93A—C93—H93B	108.3
C2—N21—H21A	120.5 (13)	O95—C94—C93	113.83 (14)
C2—N21—H21B	118.4 (14)	O95—C94—H94A	108.8
H21A—N21—H21B	121.0 (19)	C93—C94—H94A	108.8
C2—N3—C4	112.26 (12)	O95—C94—H94B	108.8
N3—C4—N9	127.04 (13)	C93—C94—H94B	108.8
N3—C4—C5	128.03 (14)	H94A—C94—H94B	107.7
N9—C4—C5	104.91 (13)	C94—O95—H95	109.5
C4—C5—N7	111.46 (13)	C6'—N1'—C2'	122.69 (15)
C4—C5—C6	118.99 (13)	C6'—N1'—H1'	116.3 (14)
N7—C5—C6	129.50 (13)	C2'—N1'—H1'	121.0 (14)
O61—C6—N1	120.80 (14)	O21'—C2'—N3'	122.22 (14)
O61—C6—C5	126.83 (14)	O21'—C2'—N1'	119.44 (15)
N1—C6—C5	112.33 (12)	N3'—C2'—N1'	118.34 (14)
C8—N7—C5	103.93 (12)	C4'—N3'—C2'	120.48 (14)
N7—C8—N9	113.38 (13)	N41'—C4'—N3'	119.83 (15)
N7—C8—H8	123.3	N41'—C4'—C5'	120.39 (15)
N9—C8—H8	123.3	N3'—C4'—C5'	119.78 (15)
C8—N9—C4	106.31 (12)	C4'—N41'—H41A	119.3 (15)
C8—N9—C91	123.38 (12)	C4'—N41'—H41B	122.7 (15)
C4—N9—C91	130.10 (12)	H41A—N41'—H41B	118 (2)
O92—C91—N9	110.74 (11)	C6'—C5'—F51'	121.44 (15)
O92—C91—H91A	109.5	C6'—C5'—C4'	120.64 (15)
N9—C91—H91A	109.5	F51'—C5'—C4'	117.92 (15)
O92—C91—H91B	109.5	C5'—C6'—N1'	118.05 (15)
N9—C91—H91B	109.5	C5'—C6'—H6'	121.0
H91A—C91—H91B	108.1	N1'—C6'—H6'	121.0
C91—O92—C93	112.19 (11)
C6—N1—C2—N3	−1.9 (2)	C5—C4—N9—C8	0.70 (14)
C6—N1—C2—N21	176.72 (13)	N3—C4—N9—C91	−3.5 (2)
N21—C2—N3—C4	−177.76 (13)	C5—C4—N9—C91	175.42 (13)
N1—C2—N3—C4	0.79 (19)	C8—N9—C91—O92	73.11 (16)
C2—N3—C4—N9	178.48 (13)	C4—N9—C91—O92	−100.82 (16)
C2—N3—C4—C5	−0.2 (2)	N9—C91—O92—C93	77.46 (15)
N3—C4—C5—N7	178.21 (12)	C91—O92—C93—C94	−171.75 (13)
N9—C4—C5—N7	−0.67 (15)	O92—C93—C94—O95	−63.25 (18)
N3—C4—C5—C6	0.5 (2)	C6'—N1'—C2'—O21'	−179.03 (13)
N9—C4—C5—C6	−178.37 (12)	C6'—N1'—C2'—N3'	0.5 (2)
C2—N1—C6—O61	−176.19 (13)	O21'—C2'—N3'—C4'	179.74 (13)
C2—N1—C6—C5	2.03 (19)	N1'—C2'—N3'—C4'	0.2 (2)
C4—C5—C6—O61	176.76 (13)	C2'—N3'—C4'—N41'	178.75 (13)
N7—C5—C6—O61	−0.5 (2)	C2'—N3'—C4'—C5'	−1.0 (2)
C4—C5—C6—N1	−1.33 (18)	N41'—C4'—C5'—C6'	−178.61 (14)
N7—C5—C6—N1	−178.55 (13)	N3'—C4'—C5'—C6'	1.2 (2)
C4—C5—N7—C8	0.36 (15)	N41'—C4'—C5'—F51'	1.3 (2)
C6—C5—N7—C8	177.75 (14)	N3'—C4'—C5'—F51'	−178.90 (12)
C5—N7—C8—N9	0.11 (15)	F51'—C5'—C6'—N1'	179.60 (12)
N7—C8—N9—C4	−0.53 (16)	C4'—C5'—C6'—N1'	−0.5 (2)
N7—C8—N9—C91	−175.70 (12)	C2'—N1'—C6'—C5'	−0.4 (2)
N3—C4—N9—C8	−178.21 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3′	0.90 (2)	2.00 (2)	2.8964 (18)	176 (2)
N21—H21B···N3^i	0.87 (2)	2.20 (2)	3.0698 (19)	177 (2)
N21—H21A···O21′	0.88 (2)	2.05 (2)	2.9317 (19)	179.7 (19)
O95—H95···N7^ii	0.84	2.32	3.0663 (18)	148
O95—H95···O61^ii	0.84	2.47	3.1112 (16)	134
N1′—H1′···O92^iii	0.88 (2)	2.22 (2)	3.0246 (18)	151.6 (19)
N41′—H41A···O61	0.91 (2)	1.88 (2)	2.7844 (18)	175 (2)

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y+1, z; (iii) x, −y+3/2, z+1/2.