Cocrystals of 5-fluorocytosine. II. Coformers with variable hydrogen-bonding sites

Two flexible molecules, biuret and 6-acetamidouracil, were cocrystallized with 5-fluorocytosine to study their conformational preferences. In the cocrystal with 5-fluorocytosine (I), biuret exhibits the same conformation as in its hydrate. In contrast, 6-acetamidouracil can adopt two main conformations depending on its crystal environment: in crystal (II) the trans form characterized by an intramolecular hydrogen bond is observed, while in the cocrystal with 5-fluorocytosine (III), the complementary binding induces the cis form. Three cocrystals of 6-methylisocytosine demonstrate that complementary binding enables the crystallization of a specific tautomer. In the cocrystals with 5-fluorocytosine, (IVa) and (IVb), only the 3H tautomer of 6-methylisocytosine is present, whereas in the cocrystal with 6-aminoisocytosine, (V), the 1H tautomeric form is adopted. The complexes observed in the cocrystals are stabilized by three hydrogen bonds similar to those constituting the Watson-Crick C·G base pair.

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), (III), (V); Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008) for (II), (IVa), (IVb).

(I) ;

Crystal data

C4H4FN3O·C2H5N3O2·C2H6OS	Z = 2
Mr = 310.32	F(000) = 324
Triclinic, P1	Dx = 1.481 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4065 (17) Å	Cell parameters from 4300 reflections
b = 8.9045 (18) Å	θ = 3.4–25.9°
c = 10.6441 (19) Å	µ = 0.27 mm^−1
α = 111.163 (15)°	T = 173 K
β = 96.337 (15)°	Needle, yellow
γ = 105.703 (16)°	0.60 × 0.30 × 0.20 mm
V = 695.8 (2) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	2617 independent reflections
Radiation source: fine-focus sealed tube	1669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.144
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan MULABS (Blessing, 1995; Spek, 2009)	h = −10→10
Tmin = 0.856, Tmax = 0.948	k = −9→10
4530 measured reflections	l = −12→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)] = 0.094	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.282	w = 1/[σ^2(Fo^2) + (0.1896P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
2617 reflections	Δρmax = 0.62 e Å^−3
208 parameters	Δρmin = −0.85 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: 0.07 (2)

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'	0.8716 (5)	0.2557 (6)	0.5405 (4)	0.0314 (10)
H1'	0.967 (4)	0.239 (7)	0.557 (6)	0.038*
C2'	0.7556 (6)	0.2210 (7)	0.6168 (5)	0.0309 (11)
O21'	0.7982 (4)	0.1873 (5)	0.7168 (3)	0.0365 (9)
N3'	0.5979 (5)	0.2314 (5)	0.5852 (4)	0.0281 (9)
C4'	0.5572 (6)	0.2738 (6)	0.4805 (5)	0.0272 (10)
N41'	0.4029 (5)	0.2823 (6)	0.4520 (4)	0.0343 (10)
H41	0.360 (7)	0.298 (7)	0.381 (4)	0.041*
H42	0.347 (7)	0.288 (8)	0.519 (4)	0.041*
C5'	0.6814 (6)	0.3154 (7)	0.4050 (5)	0.0309 (11)
F51'	0.6359 (4)	0.3625 (4)	0.3020 (3)	0.0396 (8)
C6'	0.8355 (6)	0.3040 (6)	0.4352 (5)	0.0305 (11)
H6'	0.9179	0.3288	0.3848	0.037*
N1	0.0683 (5)	0.0641 (6)	0.7517 (4)	0.0353 (10)
H11	0.081 (8)	0.015 (7)	0.809 (5)	0.042*
H12	−0.029 (5)	0.079 (7)	0.729 (6)	0.042*
C2	0.1959 (6)	0.1306 (6)	0.7020 (4)	0.0270 (10)
O21	0.1784 (4)	0.1955 (5)	0.6187 (3)	0.0375 (9)
N3	0.3545 (5)	0.1198 (5)	0.7424 (4)	0.0286 (9)
H3	0.421 (6)	0.151 (7)	0.691 (5)	0.034*
C4	0.4028 (6)	0.0611 (6)	0.8403 (4)	0.0286 (10)
O41	0.3035 (4)	0.0088 (5)	0.9063 (3)	0.0345 (9)
N5	0.5639 (5)	0.0647 (6)	0.8586 (4)	0.0378 (11)
H51	0.587 (8)	0.028 (7)	0.922 (5)	0.045*
H52	0.617 (7)	0.076 (8)	0.795 (5)	0.045*
S1A	0.12039 (19)	0.27830 (19)	0.12286 (14)	0.0425 (5)
O1A	0.1647 (5)	0.3395 (6)	0.2785 (4)	0.0503 (11)
C1A	−0.0443 (7)	0.3587 (8)	0.0881 (6)	0.0472 (15)
H1A1	−0.1477	0.2991	0.1085	0.071*
H1A2	−0.0669	0.3399	−0.0097	0.071*
H1A3	−0.0087	0.4814	0.1463	0.071*
C2A	0.2884 (8)	0.4160 (8)	0.0838 (6)	0.0493 (15)
H2A1	0.3094	0.5353	0.1456	0.074*
H2A2	0.2554	0.4002	−0.0125	0.074*
H2A3	0.3921	0.3877	0.0971	0.074*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1'	0.023 (2)	0.048 (3)	0.0268 (19)	0.0117 (18)	0.0075 (15)	0.0196 (19)
C2'	0.021 (2)	0.044 (3)	0.029 (2)	0.008 (2)	0.0048 (17)	0.020 (2)
O21'	0.0294 (19)	0.060 (2)	0.0368 (18)	0.0208 (17)	0.0108 (14)	0.0333 (18)
N3'	0.0194 (19)	0.034 (2)	0.0299 (19)	0.0072 (16)	0.0016 (15)	0.0150 (17)
C4'	0.024 (2)	0.031 (3)	0.028 (2)	0.0095 (19)	0.0059 (17)	0.0139 (19)
N41'	0.025 (2)	0.055 (3)	0.036 (2)	0.017 (2)	0.0071 (17)	0.031 (2)
C5'	0.032 (3)	0.041 (3)	0.025 (2)	0.012 (2)	0.0062 (18)	0.020 (2)
F51'	0.0402 (17)	0.055 (2)	0.0386 (15)	0.0191 (14)	0.0112 (12)	0.0334 (15)
C6'	0.028 (2)	0.036 (3)	0.025 (2)	0.003 (2)	0.0072 (17)	0.016 (2)
N1	0.025 (2)	0.053 (3)	0.039 (2)	0.014 (2)	0.0080 (17)	0.030 (2)
C2	0.021 (2)	0.034 (3)	0.025 (2)	0.0086 (19)	0.0029 (16)	0.0132 (19)
O21	0.0245 (18)	0.060 (2)	0.0413 (19)	0.0136 (16)	0.0101 (14)	0.0347 (18)
N3	0.0177 (19)	0.044 (3)	0.0283 (19)	0.0061 (17)	0.0026 (14)	0.0232 (19)
C4	0.030 (3)	0.033 (3)	0.023 (2)	0.009 (2)	0.0014 (17)	0.0133 (19)
O41	0.0291 (18)	0.053 (2)	0.0349 (17)	0.0168 (16)	0.0103 (14)	0.0304 (17)
N5	0.020 (2)	0.062 (3)	0.037 (2)	0.0092 (19)	0.0025 (16)	0.031 (2)
S1A	0.0480 (9)	0.0420 (9)	0.0384 (8)	0.0108 (6)	0.0109 (6)	0.0200 (6)
O1A	0.043 (2)	0.086 (3)	0.041 (2)	0.030 (2)	0.0113 (17)	0.040 (2)
C1A	0.037 (3)	0.058 (4)	0.037 (3)	0.000 (3)	−0.011 (2)	0.027 (3)
C2A	0.048 (3)	0.055 (4)	0.036 (3)	0.006 (3)	0.015 (2)	0.015 (3)

Geometric parameters (Å, º)

N1'—C6'	1.369 (6)	C2—N3	1.394 (6)
N1'—C2'	1.378 (6)	N3—C4	1.392 (6)
N1'—H1'	0.87 (2)	N3—H3	0.88 (2)
C2'—O21'	1.247 (5)	C4—O41	1.249 (6)
C2'—N3'	1.367 (6)	C4—N5	1.337 (6)
N3'—C4'	1.338 (6)	N5—H51	0.88 (2)
C4'—N41'	1.328 (6)	N5—H52	0.87 (2)
C4'—C5'	1.437 (7)	S1A—O1A	1.511 (4)
N41'—H41	0.87 (2)	S1A—C1A	1.784 (6)
N41'—H42	0.89 (2)	S1A—C2A	1.798 (6)
C5'—C6'	1.340 (7)	C1A—H1A1	0.9800
C5'—F51'	1.360 (5)	C1A—H1A2	0.9800
C6'—H6'	0.9500	C1A—H1A3	0.9800
N1—C2	1.338 (6)	C2A—H2A1	0.9800
N1—H11	0.88 (2)	C2A—H2A2	0.9800
N1—H12	0.89 (2)	C2A—H2A3	0.9800
C2—O21	1.237 (5)
C6'—N1'—C2'	122.1 (4)	C4—N3—C2	127.6 (4)
C6'—N1'—H1'	120 (4)	C4—N3—H3	124 (4)
C2'—N1'—H1'	118 (4)	C2—N3—H3	108 (4)
O21'—C2'—N3'	121.1 (4)	O41—C4—N5	122.3 (4)
O21'—C2'—N1'	119.6 (4)	O41—C4—N3	122.8 (4)
N3'—C2'—N1'	119.3 (4)	N5—C4—N3	114.9 (4)
C4'—N3'—C2'	120.0 (4)	C4—N5—H51	111 (4)
N41'—C4'—N3'	118.6 (4)	C4—N5—H52	117 (4)
N41'—C4'—C5'	121.3 (4)	H51—N5—H52	130 (6)
N3'—C4'—C5'	120.0 (4)	O1A—S1A—C1A	104.9 (3)
C4'—N41'—H41	126 (4)	O1A—S1A—C2A	105.4 (3)
C4'—N41'—H42	115 (4)	C1A—S1A—C2A	98.5 (3)
H41—N41'—H42	119 (5)	S1A—C1A—H1A1	109.5
C6'—C5'—F51'	122.1 (4)	S1A—C1A—H1A2	109.5
C6'—C5'—C4'	119.9 (4)	H1A1—C1A—H1A2	109.5
F51'—C5'—C4'	118.0 (4)	S1A—C1A—H1A3	109.5
C5'—C6'—N1'	118.6 (4)	H1A1—C1A—H1A3	109.5
C5'—C6'—H6'	120.7	H1A2—C1A—H1A3	109.5
N1'—C6'—H6'	120.7	S1A—C2A—H2A1	109.5
C2—N1—H11	123 (4)	S1A—C2A—H2A2	109.5
C2—N1—H12	116 (4)	H2A1—C2A—H2A2	109.5
H11—N1—H12	121 (6)	S1A—C2A—H2A3	109.5
O21—C2—N1	123.2 (4)	H2A1—C2A—H2A3	109.5
O21—C2—N3	118.7 (4)	H2A2—C2A—H2A3	109.5
N1—C2—N3	118.0 (4)
C6'—N1'—C2'—O21'	−175.8 (5)	N3'—C4'—C5'—F51'	−178.1 (4)
C6'—N1'—C2'—N3'	1.3 (7)	F51'—C5'—C6'—N1'	180.0 (4)
O21'—C2'—N3'—C4'	177.6 (5)	C4'—C5'—C6'—N1'	−1.4 (8)
N1'—C2'—N3'—C4'	0.5 (7)	C2'—N1'—C6'—C5'	−0.8 (8)
C2'—N3'—C4'—N41'	179.8 (5)	O21—C2—N3—C4	175.9 (4)
C2'—N3'—C4'—C5'	−2.7 (7)	N1—C2—N3—C4	−6.5 (8)
N41'—C4'—C5'—C6'	−179.3 (5)	C2—N3—C4—O41	0.0 (8)
N3'—C4'—C5'—C6'	3.2 (8)	C2—N3—C4—N5	179.9 (5)
N41'—C4'—C5'—F51'	−0.6 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1′—H1′···O21^i	0.87 (2)	2.01 (2)	2.870 (5)	172 (5)
N41′—H42···O21	0.89 (2)	2.04 (3)	2.872 (5)	156 (6)
N41′—H41···O1A	0.87 (2)	2.06 (4)	2.845 (5)	149 (5)
N1—H12···O21′^ii	0.89 (2)	1.96 (3)	2.820 (5)	162 (5)
N1—H11···O41	0.88 (2)	2.06 (5)	2.694 (5)	128 (5)
N3—H3···N3′	0.88 (2)	2.09 (2)	2.972 (5)	174 (5)
N5—H51···O41^iii	0.88 (2)	2.12 (3)	2.982 (5)	166 (6)
N5—H52···O21′	0.87 (2)	2.01 (3)	2.834 (6)	156 (6)

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

(II)

Crystal data

C6H7N3O3	F(000) = 352
Mr = 169.15	Dx = 1.563 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1601 reflections
a = 11.4303 (12) Å	θ = 3.4–26.0°
b = 7.1695 (8) Å	µ = 0.13 mm^−1
c = 8.9753 (11) Å	T = 173 K
β = 102.194 (9)°	Block, yellow
V = 718.93 (14) Å^3	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection

STOE IPDS II two-circle- diffractometer	773 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.187
Graphite monochromator	θmax = 25.6°, θmin = 3.4°
ω scans	h = −13→13
3983 measured reflections	k = −8→8
1337 independent reflections	l = −10→10

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ^2(Fo^2) + (0.0642P)^2] where P = (Fo^2 + 2Fc^2)/3
1337 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.28 e Å^−3
3 restraints	Δρmin = −0.27 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	0.7409 (3)	0.2480 (4)	0.5015 (4)	0.0238 (7)
H1	0.797 (3)	0.228 (6)	0.449 (4)	0.029*
C2	0.6872 (3)	0.0981 (5)	0.5530 (4)	0.0237 (8)
N3	0.6043 (3)	0.1391 (4)	0.6365 (3)	0.0247 (7)
H3	0.565 (3)	0.048 (4)	0.669 (4)	0.030*
C4	0.5720 (3)	0.3175 (5)	0.6727 (4)	0.0211 (8)
C5	0.6314 (3)	0.4668 (5)	0.6152 (4)	0.0233 (8)
H5	0.6143	0.5924	0.6365	0.028*
C6	0.7129 (3)	0.4277 (5)	0.5294 (4)	0.0232 (7)
O21	0.7141 (2)	−0.0628 (4)	0.5264 (3)	0.0323 (6)
O41	0.4959 (2)	0.3338 (4)	0.7509 (3)	0.0293 (6)
N61	0.7704 (3)	0.5681 (4)	0.4679 (4)	0.0254 (7)
H61	0.744 (3)	0.679 (3)	0.482 (5)	0.031*
C62	0.8584 (3)	0.5485 (5)	0.3849 (4)	0.0262 (8)
C63	0.9059 (4)	0.7292 (6)	0.3378 (5)	0.0323 (9)
H63A	0.9489	0.7060	0.2559	0.048*
H63B	0.9607	0.7849	0.4253	0.048*
H63C	0.8392	0.8149	0.3012	0.048*
O621	0.8944 (2)	0.3960 (4)	0.3520 (3)	0.0343 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0282 (16)	0.0172 (14)	0.0278 (16)	−0.0002 (13)	0.0102 (13)	−0.0013 (12)
C2	0.0261 (18)	0.021 (2)	0.0236 (18)	0.0016 (15)	0.0054 (14)	−0.0006 (14)
N3	0.0308 (16)	0.0136 (14)	0.0315 (16)	−0.0018 (13)	0.0103 (13)	0.0018 (12)
C4	0.0213 (16)	0.0206 (18)	0.0222 (18)	0.0043 (15)	0.0066 (14)	−0.0008 (14)
C5	0.0246 (18)	0.0130 (17)	0.0311 (19)	0.0021 (14)	0.0035 (16)	0.0014 (14)
C6	0.0261 (17)	0.0194 (17)	0.0230 (17)	0.0015 (15)	0.0027 (14)	0.0024 (15)
O21	0.0413 (15)	0.0169 (13)	0.0419 (15)	0.0046 (12)	0.0158 (12)	−0.0025 (12)
O41	0.0316 (13)	0.0226 (14)	0.0373 (14)	0.0004 (11)	0.0156 (12)	−0.0005 (11)
N61	0.0277 (15)	0.0152 (14)	0.0357 (17)	0.0033 (13)	0.0120 (13)	0.0005 (14)
C62	0.0229 (16)	0.028 (2)	0.0287 (18)	0.0011 (17)	0.0082 (15)	0.0020 (16)
C63	0.032 (2)	0.035 (2)	0.033 (2)	−0.0040 (17)	0.0117 (17)	0.0062 (17)
O621	0.0379 (14)	0.0290 (15)	0.0414 (16)	0.0035 (12)	0.0205 (12)	−0.0039 (12)

Geometric parameters (Å, º)

N1—C6	1.363 (5)	C5—H5	0.9500
N1—C2	1.365 (5)	C6—N61	1.380 (5)
N1—H1	0.885 (19)	N61—C62	1.380 (4)
C2—O21	1.230 (4)	N61—H61	0.867 (19)
C2—N3	1.359 (4)	C62—O621	1.226 (4)
N3—C4	1.389 (5)	C62—C63	1.500 (5)
N3—H3	0.880 (19)	C63—H63A	0.9800
C4—O41	1.233 (4)	C63—H63B	0.9800
C4—C5	1.422 (5)	C63—H63C	0.9800
C5—C6	1.356 (5)
C6—N1—C2	122.8 (3)	C5—C6—N1	121.0 (3)
C6—N1—H1	119 (3)	C5—C6—N61	121.2 (3)
C2—N1—H1	119 (3)	N1—C6—N61	117.7 (3)
O21—C2—N3	122.8 (3)	C62—N61—C6	127.2 (3)
O21—C2—N1	121.6 (3)	C62—N61—H61	119 (3)
N3—C2—N1	115.6 (3)	C6—N61—H61	114 (3)
C2—N3—C4	125.4 (3)	O621—C62—N61	122.7 (3)
C2—N3—H3	119 (3)	O621—C62—C63	122.9 (3)
C4—N3—H3	115 (3)	N61—C62—C63	114.4 (3)
O41—C4—N3	118.3 (3)	C62—C63—H63A	109.5
O41—C4—C5	125.7 (3)	C62—C63—H63B	109.5
N3—C4—C5	115.9 (3)	H63A—C63—H63B	109.5
C6—C5—C4	119.2 (3)	C62—C63—H63C	109.5
C6—C5—H5	120.4	H63A—C63—H63C	109.5
C4—C5—H5	120.4	H63B—C63—H63C	109.5
C6—N1—C2—O21	−179.9 (3)	C4—C5—C6—N1	−1.9 (5)
C6—N1—C2—N3	−0.9 (5)	C4—C5—C6—N61	178.3 (3)
O21—C2—N3—C4	178.7 (3)	C2—N1—C6—C5	2.0 (5)
N1—C2—N3—C4	−0.4 (5)	C2—N1—C6—N61	−178.1 (3)
C2—N3—C4—O41	−179.4 (4)	C5—C6—N61—C62	176.9 (4)
C2—N3—C4—C5	0.5 (5)	N1—C6—N61—C62	−2.9 (5)
O41—C4—C5—C6	−179.5 (4)	C6—N61—C62—O621	2.0 (6)
N3—C4—C5—C6	0.7 (4)	C6—N61—C62—C63	−178.2 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O621	0.89 (2)	1.96 (3)	2.645 (4)	133 (4)
N3—H3···O41^i	0.88 (2)	1.89 (2)	2.759 (4)	171 (4)
N61—H61···O21^ii	0.87 (2)	1.94 (2)	2.799 (4)	170 (4)

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

(III) ;

Crystal data

C4H4FN3O·C6H7N3O3·C2H6OS	F(000) = 784
Mr = 376.38	Dx = 1.547 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9551 reflections
a = 9.4478 (9) Å	θ = 3.5–25.9°
b = 23.7171 (16) Å	µ = 0.25 mm^−1
c = 7.2635 (7) Å	T = 173 K
β = 96.700 (8)°	Plate, colourless
V = 1616.4 (2) Å^3	0.40 × 0.20 × 0.20 mm
Z = 4

Data collection

STOE IPDS II two-circle- diffractometer	3031 independent reflections
Radiation source: fine-focus sealed tube	2410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.116
ω scans	θmax = 25.7°, θmin = 3.5°
Absorption correction: multi-scan MULABS (Blessing, 1995; Spek, 2009)	h = −11→11
Tmin = 0.906, Tmax = 0.952	k = −28→27
15378 measured reflections	l = −8→8

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0617P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3031 reflections	Δρmax = 0.35 e Å^−3
257 parameters	Δρmin = −0.34 e Å^−3
3 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: 0.013 (2)

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	0.59734 (17)	0.19712 (7)	0.7444 (2)	0.0177 (4)
H1	0.567 (3)	0.2323 (12)	0.764 (4)	0.037 (7)*
C2	0.5152 (2)	0.15203 (8)	0.7863 (3)	0.0190 (4)
N3	0.57290 (19)	0.09962 (7)	0.7627 (2)	0.0215 (4)
H3	0.519 (3)	0.0707 (12)	0.791 (3)	0.034 (7)*
C4	0.7085 (2)	0.08978 (9)	0.7085 (3)	0.0216 (4)
C5	0.7869 (2)	0.13904 (9)	0.6647 (3)	0.0206 (4)
H5	0.8775	0.1352	0.6215	0.025*
C6	0.7306 (2)	0.19125 (8)	0.6853 (2)	0.0172 (4)
O21	0.39637 (15)	0.15835 (6)	0.8383 (2)	0.0247 (3)
O41	0.75244 (17)	0.04058 (6)	0.7000 (2)	0.0336 (4)
N61	0.79417 (18)	0.24263 (7)	0.6552 (2)	0.0195 (4)
H61	0.742 (3)	0.2729 (12)	0.666 (3)	0.031 (7)*
C62	0.9303 (2)	0.25058 (8)	0.6083 (3)	0.0199 (4)
C63	0.9735 (2)	0.31148 (9)	0.5951 (3)	0.0238 (4)
H63A	1.0017	0.3264	0.7198	0.036*
H63B	0.8929	0.3334	0.5352	0.036*
H63C	1.0539	0.3143	0.5217	0.036*
O621	1.01090 (16)	0.21157 (7)	0.5819 (2)	0.0319 (4)
N1'	0.49640 (18)	0.40516 (7)	0.7573 (2)	0.0220 (4)
H1'	0.545 (3)	0.4347 (13)	0.712 (4)	0.041 (7)*
C2'	0.5489 (2)	0.35137 (8)	0.7394 (3)	0.0189 (4)
N3'	0.47484 (17)	0.30652 (7)	0.7958 (2)	0.0189 (4)
C4'	0.3505 (2)	0.31435 (8)	0.8658 (2)	0.0180 (4)
C5'	0.2968 (2)	0.37054 (8)	0.8797 (3)	0.0200 (4)
C6'	0.3703 (2)	0.41491 (9)	0.8263 (3)	0.0221 (4)
H6'	0.3354	0.4522	0.8363	0.027*
O21'	0.66438 (15)	0.34530 (6)	0.6732 (2)	0.0247 (3)
N41'	0.27940 (19)	0.27032 (8)	0.9215 (3)	0.0238 (4)
H41C	0.195 (3)	0.2771 (12)	0.974 (4)	0.042 (7)*
H41D	0.318 (3)	0.2369 (12)	0.903 (3)	0.033 (7)*
F51'	0.16909 (12)	0.37693 (5)	0.94694 (18)	0.0297 (3)
S1A	0.78134 (6)	0.52065 (3)	0.77666 (8)	0.0277 (2)	0.945 (3)
O1A	0.62937 (17)	0.50776 (7)	0.6952 (3)	0.0400 (5)
C1A	0.8560 (3)	0.56068 (11)	0.6043 (4)	0.0415 (6)
H1A1	0.8129	0.5983	0.5959	0.062*	0.945 (3)
H1A2	0.8371	0.5416	0.4842	0.062*	0.945 (3)
H1A3	0.9592	0.5641	0.6379	0.062*	0.945 (3)
H1A4	0.7988	0.5854	0.5169	0.062*	0.055 (3)
H1A5	0.9506	0.5556	0.5639	0.062*	0.055 (3)
H1A6	0.8658	0.5777	0.7281	0.062*	0.055 (3)
C2A	0.8792 (3)	0.45750 (11)	0.7566 (4)	0.0407 (6)
H2A1	0.8508	0.4295	0.8445	0.061*	0.945 (3)
H2A2	0.9813	0.4653	0.7840	0.061*	0.945 (3)
H2A3	0.8594	0.4428	0.6301	0.061*	0.945 (3)
H2A4	0.8369	0.4199	0.7617	0.061*	0.055 (3)
H2A5	0.8887	0.4745	0.8804	0.061*	0.055 (3)
H2A6	0.9734	0.4544	0.7136	0.061*	0.055 (3)
S1A'	0.7752 (14)	0.4977 (6)	0.611 (2)	0.067 (6)*	0.055 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0171 (8)	0.0129 (9)	0.0241 (8)	0.0008 (7)	0.0062 (6)	0.0003 (6)
C2	0.0194 (10)	0.0152 (10)	0.0225 (9)	−0.0013 (8)	0.0028 (8)	−0.0013 (7)
N3	0.0212 (8)	0.0125 (8)	0.0318 (9)	−0.0015 (7)	0.0073 (7)	−0.0014 (7)
C4	0.0216 (10)	0.0151 (11)	0.0288 (11)	−0.0002 (8)	0.0055 (8)	−0.0023 (8)
C5	0.0188 (9)	0.0163 (10)	0.0274 (10)	−0.0003 (8)	0.0063 (8)	−0.0026 (8)
C6	0.0177 (9)	0.0159 (10)	0.0181 (9)	−0.0010 (8)	0.0031 (7)	−0.0004 (7)
O21	0.0186 (7)	0.0191 (8)	0.0380 (8)	−0.0005 (6)	0.0103 (6)	0.0006 (6)
O41	0.0310 (8)	0.0127 (8)	0.0601 (10)	0.0013 (7)	0.0180 (7)	−0.0026 (7)
N61	0.0179 (8)	0.0136 (9)	0.0279 (8)	0.0010 (7)	0.0065 (7)	−0.0006 (7)
C62	0.0185 (9)	0.0195 (10)	0.0223 (9)	−0.0014 (8)	0.0056 (7)	0.0009 (8)
C63	0.0211 (10)	0.0189 (11)	0.0326 (11)	−0.0022 (8)	0.0077 (8)	0.0031 (8)
O621	0.0245 (8)	0.0188 (8)	0.0558 (10)	0.0023 (6)	0.0196 (7)	−0.0008 (7)
N1'	0.0223 (9)	0.0129 (9)	0.0319 (9)	0.0004 (7)	0.0083 (7)	−0.0004 (7)
C2'	0.0196 (9)	0.0147 (10)	0.0225 (9)	0.0011 (8)	0.0031 (8)	−0.0011 (7)
N3'	0.0189 (8)	0.0135 (8)	0.0253 (8)	0.0022 (7)	0.0066 (6)	0.0002 (6)
C4'	0.0183 (9)	0.0153 (10)	0.0199 (9)	0.0015 (8)	−0.0001 (7)	−0.0016 (7)
C5'	0.0160 (9)	0.0176 (11)	0.0269 (10)	0.0026 (8)	0.0041 (7)	−0.0045 (8)
C6'	0.0224 (10)	0.0138 (10)	0.0302 (11)	0.0023 (8)	0.0033 (8)	−0.0042 (8)
O21'	0.0225 (7)	0.0174 (8)	0.0362 (8)	0.0006 (6)	0.0118 (6)	0.0001 (6)
N41'	0.0193 (9)	0.0154 (9)	0.0384 (10)	0.0016 (7)	0.0108 (7)	−0.0007 (7)
F51'	0.0198 (6)	0.0206 (7)	0.0512 (8)	0.0003 (5)	0.0144 (5)	−0.0074 (5)
S1A	0.0297 (3)	0.0208 (3)	0.0354 (3)	−0.0042 (2)	0.0154 (2)	−0.0069 (2)
O1A	0.0225 (8)	0.0177 (8)	0.0824 (13)	−0.0004 (7)	0.0167 (8)	0.0026 (8)
C1A	0.0305 (12)	0.0288 (13)	0.0684 (17)	−0.0001 (10)	0.0194 (12)	0.0144 (12)
C2A	0.0312 (12)	0.0326 (14)	0.0592 (16)	0.0070 (11)	0.0088 (11)	0.0097 (12)

Geometric parameters (Å, º)

N1—C2	1.376 (3)	C4'—C5'	1.434 (3)
N1—C6	1.383 (2)	C5'—C6'	1.343 (3)
N1—H1	0.90 (3)	C5'—F51'	1.362 (2)
C2—O21	1.235 (2)	C6'—H6'	0.9500
C2—N3	1.376 (3)	N41'—H41C	0.94 (3)
N3—C4	1.403 (3)	N41'—H41D	0.89 (3)
N3—H3	0.89 (3)	S1A—O1A	1.5189 (18)
C4—O41	1.243 (3)	S1A—C2A	1.775 (3)
C4—C5	1.439 (3)	S1A—C1A	1.781 (2)
C5—C6	1.363 (3)	S1A—H1A6	1.6299
C5—H5	0.9500	S1A—H2A5	1.6177
C6—N61	1.387 (3)	O1A—S1A'	1.589 (13)
N61—C62	1.381 (2)	C1A—S1A'	1.682 (14)
N61—H61	0.88 (3)	C1A—H1A1	0.9800
C62—O621	1.228 (3)	C1A—H1A2	0.9800
C62—C63	1.507 (3)	C1A—H1A3	0.9800
C63—H63A	0.9800	C1A—H1A4	0.9800
C63—H63B	0.9800	C1A—H1A5	0.9800
C63—H63C	0.9800	C1A—H1A6	0.9800
N1'—C6'	1.365 (3)	C2A—S1A'	1.657 (13)
N1'—C2'	1.381 (3)	C2A—H2A1	0.9800
N1'—H1'	0.92 (3)	C2A—H2A2	0.9800
C2'—O21'	1.251 (2)	C2A—H2A3	0.9800
C2'—N3'	1.362 (3)	C2A—H2A4	0.9800
N3'—C4'	1.347 (2)	C2A—H2A5	0.9800
C4'—N41'	1.330 (3)	C2A—H2A6	0.9800
C2—N1—C6	123.19 (17)	H1A6—S1A—H2A5	111.5
C2—N1—H1	119.1 (17)	S1A—O1A—S1A'	50.0 (5)
C6—N1—H1	117.5 (18)	S1A'—C1A—H1A1	128.6
O21—C2—N3	122.36 (18)	S1A—C1A—H1A1	109.5
O21—C2—N1	121.98 (18)	S1A'—C1A—H1A2	65.1
N3—C2—N1	115.64 (17)	S1A—C1A—H1A2	109.5
C2—N3—C4	124.97 (18)	H1A1—C1A—H1A2	109.5
C2—N3—H3	115.0 (17)	S1A'—C1A—H1A3	120.6
C4—N3—H3	120.0 (17)	S1A—C1A—H1A3	109.5
O41—C4—N3	119.46 (18)	H1A1—C1A—H1A3	109.5
O41—C4—C5	124.59 (19)	H1A2—C1A—H1A3	109.5
N3—C4—C5	115.94 (18)	S1A'—C1A—H1A4	109.5
C6—C5—C4	119.72 (18)	S1A—C1A—H1A4	122.7
C6—C5—H5	120.1	H1A2—C1A—H1A4	70.8
C4—C5—H5	120.1	H1A3—C1A—H1A4	124.7
C5—C6—N1	120.43 (18)	S1A'—C1A—H1A5	109.5
C5—C6—N61	126.79 (18)	S1A—C1A—H1A5	126.5
N1—C6—N61	112.77 (17)	H1A1—C1A—H1A5	118.6
C62—N61—C6	126.27 (17)	H1A2—C1A—H1A5	75.9
C62—N61—H61	117.3 (17)	H1A4—C1A—H1A5	109.5
C6—N61—H61	116.4 (17)	S1A'—C1A—H1A6	109.5
O621—C62—N61	123.24 (19)	S1A—C1A—H1A6	65.0
O621—C62—C63	122.33 (18)	H1A1—C1A—H1A6	71.1
N61—C62—C63	114.42 (17)	H1A2—C1A—H1A6	173.8
C62—C63—H63A	109.5	H1A3—C1A—H1A6	75.7
C62—C63—H63B	109.5	H1A4—C1A—H1A6	109.5
H63A—C63—H63B	109.5	H1A5—C1A—H1A6	109.5
C62—C63—H63C	109.5	S1A'—C2A—H2A1	128.2
H63A—C63—H63C	109.5	S1A—C2A—H2A1	109.5
H63B—C63—H63C	109.5	S1A'—C2A—H2A2	121.1
C6'—N1'—C2'	121.97 (18)	S1A—C2A—H2A2	109.5
C6'—N1'—H1'	119.6 (18)	H2A1—C2A—H2A2	109.5
C2'—N1'—H1'	118.3 (18)	S1A'—C2A—H2A3	64.7
O21'—C2'—N3'	121.83 (18)	S1A—C2A—H2A3	109.5
O21'—C2'—N1'	118.78 (18)	H2A1—C2A—H2A3	109.5
N3'—C2'—N1'	119.39 (17)	H2A2—C2A—H2A3	109.5
C4'—N3'—C2'	120.48 (16)	S1A'—C2A—H2A4	109.5
N41'—C4'—N3'	120.02 (18)	S1A—C2A—H2A4	123.1
N41'—C4'—C5'	120.87 (18)	H2A2—C2A—H2A4	124.1
N3'—C4'—C5'	119.11 (17)	H2A3—C2A—H2A4	71.2
C6'—C5'—F51'	121.75 (18)	S1A'—C2A—H2A5	109.5
C6'—C5'—C4'	120.58 (18)	S1A—C2A—H2A5	64.6
F51'—C5'—C4'	117.67 (17)	H2A1—C2A—H2A5	71.5
C5'—C6'—N1'	118.45 (18)	H2A2—C2A—H2A5	75.7
C5'—C6'—H6'	120.8	H2A3—C2A—H2A5	173.5
N1'—C6'—H6'	120.8	H2A4—C2A—H2A5	109.5
C4'—N41'—H41C	118.2 (18)	S1A'—C2A—H2A6	109.5
C4'—N41'—H41D	115.2 (17)	S1A—C2A—H2A6	126.2
H41C—N41'—H41D	127 (2)	H2A1—C2A—H2A6	118.9
O1A—S1A—C2A	106.00 (11)	H2A3—C2A—H2A6	75.8
O1A—S1A—C1A	105.51 (12)	H2A4—C2A—H2A6	109.5
C2A—S1A—C1A	97.99 (12)	H2A5—C2A—H2A6	109.5
O1A—S1A—H1A6	123.2	O1A—S1A'—C2A	108.5 (8)
C2A—S1A—H1A6	114.2	O1A—S1A'—C1A	107.1 (8)
O1A—S1A—H2A5	123.9	C2A—S1A'—C1A	107.0 (8)
C1A—S1A—H2A5	114.2
C6—N1—C2—O21	−179.77 (17)	C2'—N3'—C4'—C5'	0.2 (3)
C6—N1—C2—N3	−1.2 (3)	N41'—C4'—C5'—C6'	178.80 (19)
O21—C2—N3—C4	−178.39 (18)	N3'—C4'—C5'—C6'	−1.0 (3)
N1—C2—N3—C4	3.0 (3)	N41'—C4'—C5'—F51'	−1.7 (3)
C2—N3—C4—O41	176.57 (19)	N3'—C4'—C5'—F51'	178.45 (16)
C2—N3—C4—C5	−3.9 (3)	F51'—C5'—C6'—N1'	−178.89 (17)
O41—C4—C5—C6	−177.6 (2)	C4'—C5'—C6'—N1'	0.6 (3)
N3—C4—C5—C6	2.9 (3)	C2'—N1'—C6'—C5'	0.7 (3)
C4—C5—C6—N1	−1.4 (3)	C2A—S1A—O1A—S1A'	−50.9 (6)
C4—C5—C6—N61	177.70 (18)	C1A—S1A—O1A—S1A'	52.4 (6)
C2—N1—C6—C5	0.5 (3)	O1A—S1A—C1A—S1A'	−54.9 (6)
C2—N1—C6—N61	−178.73 (16)	C2A—S1A—C1A—S1A'	54.2 (6)
C5—C6—N61—C62	−3.8 (3)	O1A—S1A—C2A—S1A'	53.8 (6)
N1—C6—N61—C62	175.31 (17)	C1A—S1A—C2A—S1A'	−54.9 (6)
C6—N61—C62—O621	2.3 (3)	S1A—O1A—S1A'—C2A	57.4 (6)
C6—N61—C62—C63	−176.68 (17)	S1A—O1A—S1A'—C1A	−57.8 (6)
C6'—N1'—C2'—O21'	179.23 (17)	S1A—C2A—S1A'—O1A	−51.4 (6)
C6'—N1'—C2'—N3'	−1.5 (3)	S1A—C2A—S1A'—C1A	63.8 (7)
O21'—C2'—N3'—C4'	−179.76 (17)	S1A—C1A—S1A'—O1A	52.0 (6)
N1'—C2'—N3'—C4'	1.0 (3)	S1A—C1A—S1A'—C2A	−64.2 (7)
C2'—N3'—C4'—N41'	−179.60 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3′	0.90 (3)	1.99 (3)	2.883 (2)	173 (3)
N3—H3···O1A^i	0.89 (3)	2.06 (3)	2.938 (2)	168 (2)
N61—H61···O21′	0.88 (3)	1.87 (3)	2.736 (2)	168 (2)
N1′—H1′···O1A	0.92 (3)	1.92 (3)	2.799 (2)	160 (3)
N41′—H41C···O621^ii	0.94 (3)	2.01 (3)	2.944 (2)	177 (3)
N41′—H41D···O21	0.89 (3)	2.08 (3)	2.966 (2)	175 (2)

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

(IVa)

Crystal data

C4H4FN3O·C5H7N3O	Z = 2
Mr = 254.24	F(000) = 264
Triclinic, P1	Dx = 1.512 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.5285 (7) Å	Cell parameters from 3861 reflections
b = 10.1491 (17) Å	θ = 3.5–25.9°
c = 12.626 (2) Å	µ = 0.12 mm^−1
α = 75.967 (13)°	T = 173 K
β = 89.785 (13)°	Block, colourless
γ = 82.918 (13)°	0.30 × 0.30 × 0.30 mm
V = 558.47 (16) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	1675 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.113
Graphite monochromator	θmax = 25.6°, θmin = 3.5°
ω scans	h = −5→5
4506 measured reflections	k = −11→12
2099 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) = 0.175	w = 1/[σ^2(Fo^2) + (0.1288P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
2099 reflections	Δρmax = 0.32 e Å^−3
189 parameters	Δρmin = −0.31 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: 0.09 (2)

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	0.6949 (4)	0.64793 (19)	0.94621 (13)	0.0305 (5)
C2	0.5925 (4)	0.6483 (2)	0.84691 (17)	0.0269 (5)
N3	0.6565 (4)	0.74133 (18)	0.75499 (14)	0.0271 (4)
H3	0.586 (6)	0.736 (3)	0.687 (2)	0.041 (7)*
C4	0.8347 (4)	0.8433 (2)	0.75656 (16)	0.0277 (5)
C5	0.9394 (5)	0.8449 (2)	0.86280 (16)	0.0308 (5)
H5	1.0570	0.9129	0.8719	0.037*
C6	0.8686 (5)	0.7476 (2)	0.95109 (16)	0.0303 (5)
N21	0.4238 (4)	0.5519 (2)	0.83545 (16)	0.0340 (5)
H21A	0.381 (6)	0.482 (3)	0.900 (2)	0.045 (7)*
H21B	0.349 (7)	0.560 (3)	0.770 (3)	0.049 (8)*
O41	0.8906 (3)	0.92251 (16)	0.66884 (12)	0.0341 (4)
C61	0.9858 (6)	0.7410 (3)	1.06419 (18)	0.0400 (6)
H61A	1.1054	0.8159	1.0611	0.060*
H61B	1.1096	0.6531	1.0924	0.060*
H61C	0.8184	0.7496	1.1125	0.060*
N1'	0.2056 (4)	0.62033 (19)	0.42542 (14)	0.0283 (4)
H1'	0.098 (6)	0.556 (3)	0.419 (2)	0.039 (7)*
C2'	0.2731 (4)	0.6363 (2)	0.52814 (16)	0.0256 (5)
N3'	0.4576 (4)	0.72922 (17)	0.53736 (13)	0.0260 (4)
C4'	0.5685 (4)	0.8070 (2)	0.44786 (17)	0.0250 (5)
C5'	0.4905 (5)	0.7911 (2)	0.34156 (16)	0.0288 (5)
C6'	0.3126 (5)	0.6974 (2)	0.33332 (17)	0.0296 (5)
H6'	0.2620	0.6851	0.2637	0.036*
O21'	0.1652 (3)	0.56351 (15)	0.61065 (11)	0.0303 (4)
N41'	0.7516 (4)	0.89500 (18)	0.45773 (15)	0.0285 (5)
H411	0.826 (6)	0.956 (3)	0.399 (2)	0.037 (7)*
H412	0.789 (6)	0.901 (3)	0.526 (2)	0.043 (7)*
F51'	0.6035 (3)	0.87174 (14)	0.25321 (10)	0.0380 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0335 (10)	0.0336 (10)	0.0241 (9)	−0.0074 (8)	−0.0029 (7)	−0.0046 (7)
C2	0.0267 (10)	0.0280 (11)	0.0255 (10)	−0.0045 (8)	−0.0005 (7)	−0.0051 (8)
N3	0.0302 (9)	0.0293 (10)	0.0222 (9)	−0.0088 (7)	−0.0043 (7)	−0.0043 (7)
C4	0.0279 (10)	0.0268 (10)	0.0287 (11)	−0.0061 (8)	−0.0028 (8)	−0.0060 (8)
C5	0.0321 (10)	0.0336 (11)	0.0288 (11)	−0.0112 (9)	−0.0063 (8)	−0.0077 (9)
C6	0.0305 (10)	0.0329 (11)	0.0280 (11)	−0.0031 (8)	−0.0035 (8)	−0.0089 (9)
N21	0.0410 (10)	0.0359 (11)	0.0253 (10)	−0.0153 (8)	−0.0040 (8)	−0.0023 (8)
O41	0.0415 (9)	0.0366 (9)	0.0254 (8)	−0.0188 (7)	−0.0033 (6)	−0.0029 (6)
C61	0.0470 (13)	0.0477 (14)	0.0267 (11)	−0.0126 (10)	−0.0057 (9)	−0.0085 (9)
N1'	0.0291 (9)	0.0302 (9)	0.0278 (9)	−0.0085 (7)	−0.0061 (7)	−0.0085 (7)
C2'	0.0231 (9)	0.0262 (10)	0.0282 (11)	−0.0038 (8)	−0.0051 (7)	−0.0074 (8)
N3'	0.0235 (8)	0.0284 (9)	0.0271 (9)	−0.0065 (7)	−0.0052 (7)	−0.0068 (7)
C4'	0.0225 (9)	0.0252 (10)	0.0269 (10)	−0.0011 (7)	−0.0048 (7)	−0.0062 (8)
C5'	0.0318 (10)	0.0297 (11)	0.0237 (10)	−0.0048 (8)	−0.0023 (8)	−0.0037 (8)
C6'	0.0311 (11)	0.0319 (11)	0.0271 (10)	−0.0057 (8)	−0.0063 (8)	−0.0088 (8)
O21'	0.0316 (8)	0.0342 (9)	0.0272 (8)	−0.0149 (6)	−0.0027 (6)	−0.0059 (6)
N41'	0.0292 (9)	0.0320 (10)	0.0265 (10)	−0.0121 (7)	−0.0025 (7)	−0.0070 (7)
F51'	0.0456 (8)	0.0452 (8)	0.0255 (7)	−0.0185 (6)	0.0028 (5)	−0.0069 (6)

Geometric parameters (Å, º)

N1—C2	1.337 (3)	C61—H61C	0.9800
N1—C6	1.368 (3)	N1'—C6'	1.359 (3)
C2—N21	1.348 (3)	N1'—C2'	1.385 (3)
C2—N3	1.362 (3)	N1'—H1'	0.88 (3)
N3—C4	1.392 (3)	C2'—O21'	1.258 (3)
N3—H3	0.93 (3)	C2'—N3'	1.360 (3)
C4—O41	1.246 (3)	N3'—C4'	1.346 (3)
C4—C5	1.429 (3)	C4'—N41'	1.319 (3)
C5—C6	1.365 (3)	C4'—C5'	1.440 (3)
C5—H5	0.9500	C5'—C6'	1.342 (3)
C6—C61	1.509 (3)	C5'—F51'	1.354 (2)
N21—H21A	0.98 (3)	C6'—H6'	0.9500
N21—H21B	0.88 (3)	N41'—H411	0.93 (3)
C61—H61A	0.9800	N41'—H412	0.90 (3)
C61—H61B	0.9800
C2—N1—C6	116.15 (18)	C6—C61—H61C	109.5
N1—C2—N21	119.53 (19)	H61A—C61—H61C	109.5
N1—C2—N3	122.68 (19)	H61B—C61—H61C	109.5
N21—C2—N3	117.78 (18)	C6'—N1'—C2'	121.81 (18)
C2—N3—C4	122.83 (18)	C6'—N1'—H1'	118.5 (18)
C2—N3—H3	119.7 (17)	C2'—N1'—H1'	119.7 (18)
C4—N3—H3	117.4 (17)	O21'—C2'—N3'	121.59 (17)
O41—C4—N3	119.30 (18)	O21'—C2'—N1'	119.28 (18)
O41—C4—C5	126.09 (19)	N3'—C2'—N1'	119.12 (19)
N3—C4—C5	114.61 (18)	C4'—N3'—C2'	120.62 (17)
C6—C5—C4	119.25 (19)	N41'—C4'—N3'	120.17 (18)
C6—C5—H5	120.4	N41'—C4'—C5'	120.3 (2)
C4—C5—H5	120.4	N3'—C4'—C5'	119.48 (19)
C5—C6—N1	124.45 (18)	C6'—C5'—F51'	122.49 (18)
C5—C6—C61	121.21 (19)	C6'—C5'—C4'	119.5 (2)
N1—C6—C61	114.34 (18)	F51'—C5'—C4'	118.00 (19)
C2—N21—H21A	119.4 (16)	C5'—C6'—N1'	119.44 (19)
C2—N21—H21B	117 (2)	C5'—C6'—H6'	120.3
H21A—N21—H21B	124 (3)	N1'—C6'—H6'	120.3
C6—C61—H61A	109.5	C4'—N41'—H411	124.4 (16)
C6—C61—H61B	109.5	C4'—N41'—H412	116.1 (19)
H61A—C61—H61B	109.5	H411—N41'—H412	119 (3)
C6—N1—C2—N21	178.94 (19)	C6'—N1'—C2'—N3'	−1.7 (3)
C6—N1—C2—N3	0.3 (3)	O21'—C2'—N3'—C4'	−179.39 (17)
N1—C2—N3—C4	0.3 (3)	N1'—C2'—N3'—C4'	1.4 (3)
N21—C2—N3—C4	−178.35 (18)	C2'—N3'—C4'—N41'	−178.74 (18)
C2—N3—C4—O41	178.00 (18)	C2'—N3'—C4'—C5'	0.0 (3)
C2—N3—C4—C5	−1.5 (3)	N41'—C4'—C5'—C6'	177.53 (19)
O41—C4—C5—C6	−177.3 (2)	N3'—C4'—C5'—C6'	−1.2 (3)
N3—C4—C5—C6	2.1 (3)	N41'—C4'—C5'—F51'	−1.9 (3)
C4—C5—C6—N1	−1.7 (3)	N3'—C4'—C5'—F51'	179.40 (17)
C4—C5—C6—C61	177.1 (2)	F51'—C5'—C6'—N1'	−179.68 (17)
C2—N1—C6—C5	0.4 (3)	C4'—C5'—C6'—N1'	1.0 (3)
C2—N1—C6—C61	−178.48 (19)	C2'—N1'—C6'—C5'	0.5 (3)
C6'—N1'—C2'—O21'	179.10 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1′—H1′···O21′^i	0.88 (3)	1.90 (3)	2.775 (2)	172 (3)
N41′—H411···O41^ii	0.93 (3)	1.94 (3)	2.810 (2)	154 (2)
N41′—H412···O41	0.90 (3)	1.93 (3)	2.828 (2)	176 (3)
N3—H3···N3′	0.93 (3)	2.00 (3)	2.930 (2)	176 (2)
N21—H21A···N1^iii	0.98 (3)	2.12 (3)	3.090 (3)	171 (2)
N21—H21B···O21′	0.88 (3)	2.17 (3)	3.045 (2)	176 (3)

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

(IVb)

Crystal data

C4H4FN3O·C5H7N3O·H2O	V = 587.63 (16) Å^3
Mr = 272.25	Z = 2
Triclinic, P1	F(000) = 284
Hall symbol: -P 1	Dx = 1.539 Mg m^−3
a = 5.1193 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3392 (15) Å	Cell parameters from 2601 reflections
c = 12.4862 (19) Å	θ = 4.0–25.7°
α = 97.103 (12)°	µ = 0.13 mm^−1
β = 93.662 (13)°	T = 173 K
γ = 95.766 (13)°	0.40 × 0.40 × 0.20 mm

Data collection

STOE IPDS II two-circle- diffractometer	1124 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.181
Graphite monochromator	θmax = 25.0°, θmin = 3.7°
ω scans	h = −5→6
8436 measured reflections	k = −11→11
2070 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.78	w = 1/[σ^2(Fo^2) + (0.0443P)^2] where P = (Fo^2 + 2Fc^2)/3
2070 reflections	(Δ/σ)max = 0.001
197 parameters	Δρmax = 0.21 e Å^−3
7 restraints	Δρmin = −0.30 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	−0.0530 (5)	−0.0477 (3)	0.7209 (2)	0.0227 (6)
C2	0.1476 (6)	0.0437 (3)	0.6993 (2)	0.0209 (7)
N3	0.2458 (5)	0.1631 (3)	0.76886 (19)	0.0210 (6)
H3	0.376 (7)	0.221 (3)	0.753 (3)	0.025*
C4	0.1448 (6)	0.2007 (3)	0.8679 (2)	0.0214 (7)
C5	−0.0698 (6)	0.1053 (3)	0.8911 (2)	0.0246 (7)
H5	−0.1526	0.1242	0.9566	0.030*
C6	−0.1578 (6)	−0.0146 (3)	0.8186 (2)	0.0234 (7)
N21	0.2636 (6)	0.0212 (3)	0.6061 (2)	0.0303 (7)
H21A	0.198 (7)	−0.059 (3)	0.565 (2)	0.036*
H21B	0.402 (5)	0.080 (3)	0.588 (3)	0.036*
O41	0.2478 (4)	0.3120 (2)	0.92671 (16)	0.0271 (6)
C61	−0.3800 (7)	−0.1210 (3)	0.8406 (3)	0.0306 (8)
H61A	−0.3126	−0.2130	0.8522	0.046*
H61B	−0.5117	−0.1376	0.7786	0.046*
H61C	−0.4612	−0.0823	0.9055	0.046*
N1'	1.0402 (5)	0.3988 (3)	0.6031 (2)	0.0229 (6)
H1'	1.102 (7)	0.368 (3)	0.541 (3)	0.027*
C2'	0.8096 (6)	0.3209 (3)	0.6229 (2)	0.0205 (7)
N3'	0.6997 (5)	0.3510 (2)	0.71785 (19)	0.0206 (6)
C4'	0.8169 (6)	0.4591 (3)	0.7921 (2)	0.0190 (7)
C5'	1.0530 (6)	0.5391 (3)	0.7704 (2)	0.0224 (7)
C6'	1.1624 (6)	0.5089 (3)	0.6769 (2)	0.0237 (7)
H6'	1.3208	0.5626	0.6623	0.028*
O21'	0.7045 (4)	0.2209 (2)	0.55116 (16)	0.0272 (5)
N41'	0.7071 (6)	0.4875 (3)	0.8843 (2)	0.0280 (7)
H41A	0.558 (5)	0.429 (3)	0.897 (3)	0.034*
H41B	0.786 (6)	0.557 (3)	0.935 (2)	0.034*
F51'	1.1630 (4)	0.64720 (19)	0.84809 (15)	0.0347 (5)
O1W	−0.2989 (5)	−0.3032 (2)	0.58184 (18)	0.0283 (5)
H1W	−0.439 (5)	−0.276 (3)	0.545 (2)	0.034*
H2W	−0.207 (6)	−0.228 (3)	0.623 (2)	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0247 (16)	0.0217 (13)	0.0204 (14)	−0.0022 (11)	0.0023 (11)	0.0018 (10)
C2	0.0226 (18)	0.0195 (16)	0.0192 (16)	0.0025 (13)	−0.0007 (13)	−0.0017 (12)
N3	0.0224 (16)	0.0208 (14)	0.0186 (14)	−0.0019 (11)	0.0035 (11)	−0.0003 (11)
C4	0.0218 (18)	0.0232 (16)	0.0186 (15)	0.0045 (13)	0.0010 (13)	−0.0014 (13)
C5	0.0301 (19)	0.0250 (16)	0.0183 (15)	−0.0010 (13)	0.0067 (13)	0.0020 (12)
C6	0.026 (2)	0.0223 (16)	0.0218 (16)	0.0025 (13)	0.0016 (13)	0.0036 (12)
N21	0.0322 (18)	0.0291 (15)	0.0252 (15)	−0.0056 (12)	0.0073 (12)	−0.0092 (11)
O41	0.0339 (14)	0.0249 (12)	0.0191 (11)	−0.0043 (10)	0.0082 (10)	−0.0075 (9)
C61	0.035 (2)	0.0289 (18)	0.0289 (17)	−0.0003 (15)	0.0069 (15)	0.0071 (13)
N1'	0.0259 (16)	0.0273 (14)	0.0159 (13)	0.0046 (12)	0.0065 (11)	0.0005 (11)
C2'	0.0187 (17)	0.0222 (15)	0.0203 (16)	0.0017 (12)	0.0029 (13)	0.0012 (12)
N3'	0.0206 (15)	0.0210 (13)	0.0184 (13)	0.0016 (11)	0.0025 (11)	−0.0048 (10)
C4'	0.0186 (18)	0.0189 (15)	0.0194 (16)	0.0024 (13)	0.0019 (12)	0.0011 (12)
C5'	0.0229 (18)	0.0197 (16)	0.0217 (16)	−0.0020 (13)	−0.0012 (13)	−0.0039 (12)
C6'	0.0239 (19)	0.0229 (16)	0.0237 (17)	−0.0032 (13)	0.0024 (14)	0.0047 (13)
O21'	0.0292 (14)	0.0305 (12)	0.0180 (11)	−0.0006 (10)	0.0024 (9)	−0.0088 (9)
N41'	0.0300 (17)	0.0293 (15)	0.0199 (13)	−0.0063 (12)	0.0090 (12)	−0.0113 (11)
F51'	0.0331 (12)	0.0328 (11)	0.0314 (10)	−0.0126 (8)	0.0044 (8)	−0.0108 (8)
O1W	0.0293 (14)	0.0324 (13)	0.0217 (11)	0.0021 (10)	0.0022 (10)	−0.0012 (9)

Geometric parameters (Å, º)

N1—C2	1.331 (4)	N1'—C6'	1.363 (4)
N1—C6	1.377 (4)	N1'—C2'	1.376 (4)
C2—N21	1.343 (4)	N1'—H1'	0.88 (3)
C2—N3	1.358 (4)	C2'—O21'	1.262 (3)
N3—C4	1.390 (4)	C2'—N3'	1.355 (4)
N3—H3	0.87 (3)	N3'—C4'	1.347 (4)
C4—O41	1.244 (3)	C4'—N41'	1.323 (4)
C4—C5	1.411 (4)	C4'—C5'	1.415 (4)
C5—C6	1.368 (4)	C5'—C6'	1.338 (4)
C5—H5	0.9500	C5'—F51'	1.361 (3)
C6—C61	1.496 (4)	C6'—H6'	0.9500
N21—H21A	0.871 (18)	N41'—H41A	0.924 (18)
N21—H21B	0.910 (18)	N41'—H41B	0.893 (18)
C61—H61A	0.9800	O1W—H1W	0.898 (18)
C61—H61B	0.9800	O1W—H2W	0.891 (18)
C61—H61C	0.9800
C2—N1—C6	116.2 (2)	H61A—C61—H61C	109.5
N1—C2—N21	120.9 (3)	H61B—C61—H61C	109.5
N1—C2—N3	122.5 (3)	C6'—N1'—C2'	121.5 (3)
N21—C2—N3	116.6 (3)	C6'—N1'—H1'	125 (2)
C2—N3—C4	123.0 (3)	C2'—N1'—H1'	114 (2)
C2—N3—H3	120 (2)	O21'—C2'—N3'	121.1 (3)
C4—N3—H3	117 (2)	O21'—C2'—N1'	118.6 (3)
O41—C4—N3	118.6 (3)	N3'—C2'—N1'	120.3 (3)
O41—C4—C5	126.5 (3)	C4'—N3'—C2'	119.3 (3)
N3—C4—C5	114.9 (3)	N41'—C4'—N3'	118.6 (3)
C6—C5—C4	119.5 (3)	N41'—C4'—C5'	121.5 (3)
C6—C5—H5	120.2	N3'—C4'—C5'	119.8 (3)
C4—C5—H5	120.2	C6'—C5'—F51'	121.7 (3)
C5—C6—N1	123.8 (3)	C6'—C5'—C4'	120.9 (3)
C5—C6—C61	121.6 (3)	F51'—C5'—C4'	117.4 (3)
N1—C6—C61	114.6 (3)	C5'—C6'—N1'	118.1 (3)
C2—N21—H21A	113 (2)	C5'—C6'—H6'	120.9
C2—N21—H21B	124 (2)	N1'—C6'—H6'	120.9
H21A—N21—H21B	123 (3)	C4'—N41'—H41A	119 (2)
C6—C61—H61A	109.5	C4'—N41'—H41B	119 (2)
C6—C61—H61B	109.5	H41A—N41'—H41B	122 (3)
H61A—C61—H61B	109.5	H1W—O1W—H2W	112 (3)
C6—C61—H61C	109.5
C6—N1—C2—N21	−179.9 (3)	C6'—N1'—C2'—N3'	−0.9 (5)
C6—N1—C2—N3	0.1 (4)	O21'—C2'—N3'—C4'	−179.6 (3)
N1—C2—N3—C4	−0.4 (5)	N1'—C2'—N3'—C4'	0.8 (4)
N21—C2—N3—C4	179.6 (3)	C2'—N3'—C4'—N41'	179.8 (3)
C2—N3—C4—O41	179.8 (3)	C2'—N3'—C4'—C5'	−0.3 (4)
C2—N3—C4—C5	−0.3 (4)	N41'—C4'—C5'—C6'	179.8 (3)
O41—C4—C5—C6	−178.8 (3)	N3'—C4'—C5'—C6'	−0.1 (5)
N3—C4—C5—C6	1.2 (4)	N41'—C4'—C5'—F51'	−0.2 (4)
C4—C5—C6—N1	−1.7 (5)	N3'—C4'—C5'—F51'	179.9 (3)
C4—C5—C6—C61	178.4 (3)	F51'—C5'—C6'—N1'	180.0 (3)
C2—N1—C6—C5	1.0 (5)	C4'—C5'—C6'—N1'	0.0 (5)
C2—N1—C6—C61	−179.1 (3)	C2'—N1'—C6'—C5'	0.5 (5)
C6'—N1'—C2'—O21'	179.5 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N3′	0.87 (3)	2.06 (3)	2.921 (3)	177 (3)
N21—H21A···O21′^i	0.87 (2)	2.09 (3)	2.831 (3)	143 (3)
N21—H21B···O21′	0.91 (2)	2.04 (2)	2.952 (4)	177 (3)
N1′—H1′···O1W^i	0.88 (3)	1.96 (3)	2.829 (3)	170 (3)
N41′—H41A···O41	0.92 (2)	1.92 (2)	2.845 (4)	178 (3)
N41′—H41B···O41^ii	0.89 (2)	2.02 (2)	2.807 (3)	146 (3)
O1W—H1W···O21′^iii	0.90 (2)	1.91 (2)	2.803 (3)	171 (3)
O1W—H2W···N1	0.89 (2)	2.01 (2)	2.896 (3)	171 (3)

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

(V) ;

Crystal data

C5H7N3O·C4H6N4O·2(C4H9NO)	Z = 2
Mr = 425.51	F(000) = 456
Triclinic, P1	Dx = 1.299 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9824 (11) Å	Cell parameters from 4489 reflections
b = 9.1224 (14) Å	θ = 3.2–25.8°
c = 17.651 (3) Å	µ = 0.10 mm^−1
α = 88.329 (12)°	T = 173 K
β = 89.875 (12)°	Block, colourless
γ = 75.513 (12)°	0.40 × 0.20 × 0.20 mm
V = 1088.1 (3) Å^3

Data collection

STOE IPDS II two-circle- diffractometer	2241 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.085
Graphite monochromator	θmax = 25.0°, θmin = 3.2°
ω scans	h = −8→8
8046 measured reflections	k = −10→10
3820 independent reflections	l = −21→21

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.234	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.1242P)^2] where P = (Fo^2 + 2Fc^2)/3
3820 reflections	(Δ/σ)max < 0.001
308 parameters	Δρmax = 0.29 e Å^−3
25 restraints	Δρmin = −0.29 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'	0.5870 (5)	0.5060 (4)	0.89902 (17)	0.0337 (8)
C2'	0.5765 (6)	0.5579 (5)	0.8281 (2)	0.0319 (9)
N21'	0.4953 (6)	0.7029 (4)	0.8113 (2)	0.0387 (8)
H21A	0.485 (7)	0.741 (5)	0.764 (3)	0.046*
H21B	0.437 (7)	0.771 (6)	0.844 (3)	0.046*
N3'	0.6483 (5)	0.4677 (4)	0.76900 (18)	0.0333 (8)
H3'	0.654 (6)	0.512 (5)	0.7240 (15)	0.040*
C4'	0.7408 (6)	0.3153 (5)	0.7787 (2)	0.0345 (9)
O41'	0.8079 (5)	0.2426 (3)	0.72092 (15)	0.0455 (8)
C5'	0.7480 (6)	0.2575 (5)	0.8534 (2)	0.0361 (9)
H5'	0.8046	0.1531	0.8644	0.043*
C6'	0.6705 (6)	0.3561 (5)	0.9113 (2)	0.0344 (9)
N61'	0.6760 (6)	0.3069 (4)	0.98480 (19)	0.0433 (9)
H61A	0.704 (7)	0.208 (3)	0.998 (3)	0.052*
H61B	0.580 (5)	0.362 (5)	1.013 (2)	0.052*
N1	0.7139 (5)	0.5722 (4)	0.48962 (18)	0.0348 (8)
H1	0.771 (7)	0.512 (5)	0.455 (3)	0.042*
C2	0.7217 (6)	0.5123 (5)	0.5615 (2)	0.0322 (9)
N21	0.8256 (6)	0.3716 (4)	0.5740 (2)	0.0397 (9)
H21C	0.863 (7)	0.313 (6)	0.535 (3)	0.048*
H21D	0.845 (7)	0.324 (6)	0.619 (3)	0.048*
N3	0.6296 (5)	0.5927 (4)	0.61921 (17)	0.0341 (8)
C4	0.5253 (6)	0.7405 (5)	0.6056 (2)	0.0358 (9)
O41	0.4467 (5)	0.8181 (3)	0.65967 (15)	0.0438 (8)
C5	0.5143 (6)	0.8007 (5)	0.5287 (2)	0.0391 (10)
H5	0.4383	0.9009	0.5176	0.047*
C6	0.6103 (6)	0.7164 (5)	0.4726 (2)	0.0370 (10)
C61	0.6152 (7)	0.7676 (6)	0.3908 (2)	0.0455 (11)
H611	0.5583	0.8772	0.3862	0.068*
H612	0.5382	0.7152	0.3599	0.068*
H613	0.7525	0.7438	0.3732	0.068*
O1A	0.9280 (5)	0.3183 (4)	0.41703 (17)	0.0535 (9)
C3A	1.0584 (8)	0.0510 (5)	0.3890 (3)	0.0533 (12)
H3A1	1.0974	−0.0055	0.3428	0.080*	0.750 (12)
H3A2	0.9513	0.0163	0.4138	0.080*	0.750 (12)
H3A3	1.1721	0.0340	0.4235	0.080*	0.750 (12)
H6A4	1.1167	−0.0500	0.3698	0.080*	0.250 (12)
H6A5	0.9300	0.0528	0.4120	0.080*	0.250 (12)
H6A6	1.1467	0.0751	0.4272	0.080*	0.250 (12)
C5A	1.0575 (8)	0.1418 (6)	0.2390 (3)	0.0593 (14)
H5A1	1.0494	0.1924	0.1890	0.089*	0.750 (12)
H5A2	0.9728	0.0708	0.2399	0.089*	0.750 (12)
H5A3	1.1947	0.0863	0.2495	0.089*	0.750 (12)
H5A4	1.1163	0.0341	0.2308	0.089*	0.250 (12)
H5A5	1.1452	0.2017	0.2184	0.089*	0.250 (12)
H5A6	0.9288	0.1729	0.2133	0.089*	0.250 (12)
C6A	0.9148 (8)	0.4200 (5)	0.2780 (3)	0.0521 (12)
H6A1	0.9237	0.4370	0.2232	0.078*	0.750 (12)
H6A2	0.9939	0.4776	0.3044	0.078*	0.750 (12)
H6A3	0.7764	0.4536	0.2937	0.078*	0.750 (12)
H3A4	0.9516	0.3655	0.2310	0.078*	0.250 (12)
H3A5	0.9946	0.4934	0.2838	0.078*	0.250 (12)
H3A6	0.7743	0.4734	0.2759	0.078*	0.250 (12)
C2A	0.9894 (8)	0.2146 (5)	0.3694 (3)	0.0363 (16)	0.750 (12)
N4A	0.9911 (7)	0.2557 (5)	0.2972 (2)	0.0393 (16)	0.750 (12)
C2A'	0.952 (2)	0.3081 (11)	0.3449 (4)	0.036 (5)*	0.250 (12)
N4A'	1.030 (2)	0.1678 (10)	0.3239 (5)	0.042 (5)*	0.250 (12)
O1B	0.2932 (5)	0.9505 (3)	0.91215 (18)	0.0500 (8)
C3B	0.2880 (7)	1.1311 (6)	0.8088 (3)	0.0495 (12)
H3B1	0.3379	1.0398	0.7796	0.074*
H3B2	0.3803	1.1960	0.8045	0.074*
H3B3	0.1582	1.1863	0.7890	0.074*
C5B	0.1777 (8)	1.3566 (5)	0.9220 (3)	0.0575 (13)
H5B1	0.2279	1.3717	0.8712	0.086*
H5B2	0.2402	1.4084	0.9589	0.086*
H5B3	0.0341	1.3983	0.9228	0.086*
C6B	0.2071 (8)	1.1510 (6)	1.0225 (3)	0.0543 (12)
H6B1	0.0862	1.1162	1.0297	0.081*
H6B2	0.2016	1.2388	1.0538	0.081*
H6B3	0.3222	1.0692	1.0373	0.081*
C2B	0.2689 (6)	1.0867 (6)	0.8909 (3)	0.0457 (11)
N4B	0.2242 (6)	1.1944 (5)	0.9415 (2)	0.0522 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1'	0.0392 (18)	0.0348 (19)	0.0276 (16)	−0.0095 (15)	0.0060 (14)	−0.0043 (14)
C2'	0.031 (2)	0.035 (2)	0.032 (2)	−0.0106 (17)	0.0021 (16)	−0.0093 (16)
N21'	0.051 (2)	0.030 (2)	0.0304 (18)	−0.0012 (16)	0.0060 (16)	−0.0039 (15)
N3'	0.0387 (18)	0.0341 (19)	0.0258 (16)	−0.0067 (15)	0.0027 (14)	−0.0026 (14)
C4'	0.032 (2)	0.034 (2)	0.035 (2)	−0.0042 (18)	0.0002 (16)	−0.0040 (17)
O41'	0.062 (2)	0.0378 (17)	0.0297 (14)	0.0018 (15)	0.0014 (13)	−0.0094 (12)
C5'	0.039 (2)	0.033 (2)	0.035 (2)	−0.0062 (18)	0.0004 (17)	−0.0033 (17)
C6'	0.034 (2)	0.035 (2)	0.035 (2)	−0.0097 (18)	−0.0011 (16)	−0.0045 (17)
N61'	0.057 (2)	0.037 (2)	0.0308 (18)	−0.0031 (19)	0.0045 (16)	0.0004 (15)
N1	0.0394 (19)	0.040 (2)	0.0280 (17)	−0.0146 (16)	0.0050 (14)	−0.0073 (15)
C2	0.031 (2)	0.038 (2)	0.0291 (19)	−0.0107 (18)	0.0000 (15)	−0.0028 (17)
N21	0.051 (2)	0.036 (2)	0.0317 (18)	−0.0099 (18)	0.0063 (16)	−0.0083 (16)
N3	0.0353 (18)	0.035 (2)	0.0317 (17)	−0.0082 (16)	0.0023 (14)	−0.0072 (14)
C4	0.037 (2)	0.037 (2)	0.036 (2)	−0.0128 (19)	0.0018 (17)	−0.0077 (18)
O41	0.0525 (18)	0.0403 (18)	0.0343 (15)	−0.0029 (14)	0.0043 (13)	−0.0075 (13)
C5	0.041 (2)	0.040 (2)	0.036 (2)	−0.0080 (19)	−0.0003 (17)	0.0003 (18)
C6	0.038 (2)	0.044 (3)	0.032 (2)	−0.017 (2)	−0.0014 (17)	−0.0009 (18)
C61	0.050 (3)	0.055 (3)	0.033 (2)	−0.016 (2)	0.0017 (19)	0.0034 (19)
O1A	0.059 (2)	0.065 (2)	0.0409 (17)	−0.0210 (18)	0.0152 (15)	−0.0252 (16)
C3A	0.072 (3)	0.041 (3)	0.044 (3)	−0.007 (2)	0.000 (2)	−0.006 (2)
C5A	0.070 (3)	0.066 (3)	0.048 (3)	−0.027 (3)	0.018 (2)	−0.032 (2)
C6A	0.058 (3)	0.053 (3)	0.048 (3)	−0.020 (2)	−0.004 (2)	0.004 (2)
C2A	0.036 (3)	0.038 (3)	0.036 (3)	−0.011 (3)	0.000 (2)	−0.005 (3)
N4A	0.043 (3)	0.040 (3)	0.035 (3)	−0.011 (2)	0.005 (2)	−0.010 (2)
O1B	0.063 (2)	0.0307 (17)	0.0517 (19)	−0.0038 (15)	0.0024 (15)	−0.0024 (14)
C3B	0.044 (3)	0.058 (3)	0.049 (3)	−0.017 (2)	0.000 (2)	0.004 (2)
C5B	0.054 (3)	0.035 (3)	0.084 (4)	−0.011 (2)	−0.003 (3)	−0.009 (2)
C6B	0.061 (3)	0.058 (3)	0.042 (2)	−0.012 (3)	−0.002 (2)	−0.014 (2)
C2B	0.035 (2)	0.049 (3)	0.053 (3)	−0.008 (2)	−0.006 (2)	−0.009 (2)
N4B	0.051 (2)	0.047 (2)	0.058 (2)	−0.0112 (19)	−0.0065 (19)	−0.0083 (19)

Geometric parameters (Å, º)

N1'—C2'	1.322 (5)	C3A—H3A3	0.9800
N1'—C6'	1.357 (5)	C3A—H6A4	0.9800
C2'—N21'	1.328 (5)	C3A—H6A5	0.9800
C2'—N3'	1.363 (5)	C3A—H6A6	0.9800
N21'—H21A	0.90 (5)	C5A—N4A	1.472 (5)
N21'—H21B	0.88 (5)	C5A—N4A'	1.528 (8)
N3'—C4'	1.384 (5)	C5A—H5A1	0.9800
N3'—H3'	0.89 (2)	C5A—H5A2	0.9800
C4'—O41'	1.258 (5)	C5A—H5A3	0.9800
C4'—C5'	1.401 (6)	C5A—H5A4	0.9800
C5'—C6'	1.399 (6)	C5A—H5A5	0.9800
C5'—H5'	0.9500	C5A—H5A6	0.9800
C6'—N61'	1.357 (5)	C6A—N4A	1.489 (6)
N61'—H61A	0.90 (2)	C6A—C2A'	1.517 (8)
N61'—H61B	0.89 (2)	C6A—H6A1	0.9800
N1—C6	1.359 (6)	C6A—H6A2	0.9800
N1—C2	1.363 (5)	C6A—H6A3	0.9800
N1—H1	0.86 (5)	C6A—H3A4	0.9800
C2—N21	1.319 (5)	C6A—H3A5	0.9800
C2—N3	1.339 (5)	C6A—H3A6	0.9800
N21—H21C	0.89 (5)	C2A—N4A	1.319 (6)
N21—H21D	0.88 (5)	C2A'—N4A'	1.323 (9)
N3—C4	1.377 (5)	O1B—C2B	1.258 (6)
C4—O41	1.248 (5)	C3B—C2B	1.507 (7)
C4—C5	1.445 (6)	C3B—H3B1	0.9800
C5—C6	1.343 (6)	C3B—H3B2	0.9800
C5—H5	0.9500	C3B—H3B3	0.9800
C6—C61	1.507 (6)	C5B—N4B	1.464 (6)
C61—H611	0.9800	C5B—H5B1	0.9800
C61—H612	0.9800	C5B—H5B2	0.9800
C61—H613	0.9800	C5B—H5B3	0.9800
O1A—C2A	1.276 (5)	C6B—N4B	1.484 (6)
O1A—C2A'	1.286 (8)	C6B—H6B1	0.9800
C3A—C2A	1.480 (6)	C6B—H6B2	0.9800
C3A—N4A'	1.524 (8)	C6B—H6B3	0.9800
C3A—H3A1	0.9800	C2B—N4B	1.326 (6)
C3A—H3A2	0.9800
C2'—N1'—C6'	117.1 (3)	H5A2—C5A—H5A3	109.5
N1'—C2'—N21'	120.7 (3)	N4A—C5A—H5A4	144.3
N1'—C2'—N3'	122.5 (4)	N4A'—C5A—H5A4	109.5
N21'—C2'—N3'	116.8 (4)	H5A1—C5A—H5A4	106.1
C2'—N21'—H21A	123 (3)	H5A2—C5A—H5A4	60.5
C2'—N21'—H21B	125 (3)	H5A3—C5A—H5A4	53.4
H21A—N21'—H21B	112 (4)	N4A—C5A—H5A5	89.5
C2'—N3'—C4'	122.7 (3)	N4A'—C5A—H5A5	109.5
C2'—N3'—H3'	118 (3)	H5A1—C5A—H5A5	52.7
C4'—N3'—H3'	119 (3)	H5A2—C5A—H5A5	158.6
O41'—C4'—N3'	118.0 (4)	H5A3—C5A—H5A5	71.6
O41'—C4'—C5'	126.5 (4)	H5A4—C5A—H5A5	109.5
N3'—C4'—C5'	115.5 (3)	N4A—C5A—H5A6	91.1
C6'—C5'—C4'	118.9 (4)	N4A'—C5A—H5A6	109.5
C6'—C5'—H5'	120.6	H5A1—C5A—H5A6	61.2
C4'—C5'—H5'	120.6	H5A2—C5A—H5A6	61.8
N1'—C6'—N61'	115.3 (3)	H5A3—C5A—H5A6	159.5
N1'—C6'—C5'	123.2 (4)	H5A4—C5A—H5A6	109.5
N61'—C6'—C5'	121.5 (4)	H5A5—C5A—H5A6	109.5
C6'—N61'—H61A	122 (3)	N4A—C6A—H6A1	109.5
C6'—N61'—H61B	114 (3)	C2A'—C6A—H6A1	147.7
H61A—N61'—H61B	112 (5)	N4A—C6A—H6A2	109.5
C6—N1—C2	121.6 (3)	C2A'—C6A—H6A2	87.8
C6—N1—H1	121 (3)	H6A1—C6A—H6A2	109.5
C2—N1—H1	117 (3)	N4A—C6A—H6A3	109.5
N21—C2—N3	119.7 (4)	C2A'—C6A—H6A3	88.7
N21—C2—N1	118.4 (4)	H6A1—C6A—H6A3	109.5
N3—C2—N1	121.9 (4)	H6A2—C6A—H6A3	109.5
C2—N21—H21C	119 (3)	N4A—C6A—H3A4	71.2
C2—N21—H21D	125 (3)	C2A'—C6A—H3A4	109.5
H21C—N21—H21D	115 (5)	H6A2—C6A—H3A4	125.8
C2—N3—C4	119.0 (3)	H6A3—C6A—H3A4	121.4
O41—C4—N3	119.3 (4)	N4A—C6A—H3A5	122.7
O41—C4—C5	122.4 (4)	C2A'—C6A—H3A5	109.5
N3—C4—C5	118.3 (4)	H6A1—C6A—H3A5	86.9
C6—C5—C4	120.7 (4)	H6A3—C6A—H3A5	115.8
C6—C5—H5	119.7	H3A4—C6A—H3A5	109.5
C4—C5—H5	119.7	N4A—C6A—H3A6	124.5
C5—C6—N1	118.5 (4)	C2A'—C6A—H3A6	109.5
C5—C6—C61	125.7 (4)	H6A1—C6A—H3A6	89.6
N1—C6—C61	115.8 (4)	H6A2—C6A—H3A6	112.0
C6—C61—H611	109.5	H3A4—C6A—H3A6	109.5
C6—C61—H612	109.5	H3A5—C6A—H3A6	109.5
H611—C61—H612	109.5	O1A—C2A—N4A	117.8 (4)
C6—C61—H613	109.5	O1A—C2A—C3A	124.8 (4)
H611—C61—H613	109.5	N4A—C2A—C3A	117.4 (4)
H612—C61—H613	109.5	C2A—N4A—C5A	120.7 (4)
C2A—C3A—H3A1	109.5	C2A—N4A—C6A	116.7 (4)
N4A'—C3A—H3A1	73.5	C5A—N4A—C6A	122.5 (4)
C2A—C3A—H3A2	109.5	O1A—C2A'—N4A'	112.9 (7)
N4A'—C3A—H3A2	124.7	O1A—C2A'—C6A	135.0 (7)
H3A1—C3A—H3A2	109.5	N4A'—C2A'—C6A	112.1 (6)
C2A—C3A—H3A3	109.5	C2A'—N4A'—C3A	113.6 (7)
N4A'—C3A—H3A3	121.6	C2A'—N4A'—C5A	117.3 (7)
H3A1—C3A—H3A3	109.5	C3A—N4A'—C5A	128.7 (7)
H3A2—C3A—H3A3	109.5	C2B—C3B—H3B1	109.5
C2A—C3A—H6A4	145.5	C2B—C3B—H3B2	109.5
N4A'—C3A—H6A4	109.5	H3B1—C3B—H3B2	109.5
H3A2—C3A—H6A4	91.7	C2B—C3B—H3B3	109.5
H3A3—C3A—H6A4	87.3	H3B1—C3B—H3B3	109.5
C2A—C3A—H6A5	90.1	H3B2—C3B—H3B3	109.5
N4A'—C3A—H6A5	109.5	N4B—C5B—H5B1	109.5
H3A1—C3A—H6A5	119.4	N4B—C5B—H5B2	109.5
H3A3—C3A—H6A5	116.7	H5B1—C5B—H5B2	109.5
H6A4—C3A—H6A5	109.5	N4B—C5B—H5B3	109.5
C2A—C3A—H6A6	89.0	H5B1—C5B—H5B3	109.5
N4A'—C3A—H6A6	109.5	H5B2—C5B—H5B3	109.5
H3A1—C3A—H6A6	126.8	N4B—C6B—H6B1	109.5
H3A2—C3A—H6A6	110.1	N4B—C6B—H6B2	109.5
H6A4—C3A—H6A6	109.5	H6B1—C6B—H6B2	109.5
H6A5—C3A—H6A6	109.5	N4B—C6B—H6B3	109.5
N4A—C5A—H5A1	109.5	H6B1—C6B—H6B3	109.5
N4A'—C5A—H5A1	144.2	H6B2—C6B—H6B3	109.5
N4A—C5A—H5A2	109.5	O1B—C2B—N4B	119.5 (4)
N4A'—C5A—H5A2	91.9	O1B—C2B—C3B	121.6 (4)
H5A1—C5A—H5A2	109.5	N4B—C2B—C3B	119.0 (4)
N4A—C5A—H5A3	109.5	C2B—N4B—C5B	123.8 (4)
N4A'—C5A—H5A3	88.6	C2B—N4B—C6B	119.1 (4)
H5A1—C5A—H5A3	109.5	C5B—N4B—C6B	117.0 (4)
C6'—N1'—C2'—N21'	179.4 (4)	N4A'—C3A—C2A—O1A	−177.4 (13)
C6'—N1'—C2'—N3'	−1.1 (5)	N4A'—C3A—C2A—N4A	2.9 (10)
N1'—C2'—N3'—C4'	−1.1 (6)	O1A—C2A—N4A—C5A	−179.2 (5)
N21'—C2'—N3'—C4'	178.4 (4)	C3A—C2A—N4A—C5A	0.6 (7)
C2'—N3'—C4'—O41'	−177.7 (4)	O1A—C2A—N4A—C6A	−1.8 (7)
C2'—N3'—C4'—C5'	2.8 (5)	C3A—C2A—N4A—C6A	177.9 (4)
O41'—C4'—C5'—C6'	178.2 (4)	N4A'—C5A—N4A—C2A	−3.4 (11)
N3'—C4'—C5'—C6'	−2.4 (5)	N4A'—C5A—N4A—C6A	179.4 (12)
C2'—N1'—C6'—N61'	−179.1 (4)	C2A'—C6A—N4A—C2A	0.6 (11)
C2'—N1'—C6'—C5'	1.5 (6)	C2A'—C6A—N4A—C5A	177.9 (12)
C4'—C5'—C6'—N1'	0.3 (6)	C2A—O1A—C2A'—N4A'	−2.2 (9)
C4'—C5'—C6'—N61'	−179.0 (4)	C2A—O1A—C2A'—C6A	179 (3)
C6—N1—C2—N21	−179.8 (4)	N4A—C6A—C2A'—O1A	179 (3)
C6—N1—C2—N3	−0.7 (5)	N4A—C6A—C2A'—N4A'	0.9 (8)
N21—C2—N3—C4	178.6 (4)	O1A—C2A'—N4A'—C3A	4.5 (19)
N1—C2—N3—C4	−0.5 (5)	C6A—C2A'—N4A'—C3A	−176.7 (10)
C2—N3—C4—O41	−176.7 (4)	O1A—C2A'—N4A'—C5A	177.8 (10)
C2—N3—C4—C5	2.1 (5)	C6A—C2A'—N4A'—C5A	−3.5 (18)
O41—C4—C5—C6	176.1 (4)	C2A—C3A—N4A'—C2A'	−1.2 (9)
N3—C4—C5—C6	−2.7 (6)	C2A—C3A—N4A'—C5A	−174 (2)
C4—C5—C6—N1	1.6 (6)	N4A—C5A—N4A'—C2A'	1.8 (9)
C4—C5—C6—C61	−178.1 (4)	N4A—C5A—N4A'—C3A	174 (2)
C2—N1—C6—C5	0.1 (6)	O1B—C2B—N4B—C5B	−175.0 (4)
C2—N1—C6—C61	179.8 (3)	C3B—C2B—N4B—C5B	4.5 (7)
C2A'—O1A—C2A—N4A	0.8 (11)	O1B—C2B—N4B—C6B	1.0 (6)
C2A'—O1A—C2A—C3A	−178.9 (14)	C3B—C2B—N4B—C6B	−179.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21′—H21B···O1B	0.88 (5)	2.10 (5)	2.981 (5)	174 (4)
N21′—H21A···O41	0.90 (5)	1.94 (5)	2.836 (5)	176 (4)
N3′—H3′···N3	0.89 (2)	1.96 (2)	2.839 (4)	170 (4)
N61′—H61B···N1′^i	0.89 (2)	2.15 (2)	3.019 (5)	165 (5)
N61′—H61A···O1B^i	0.90 (2)	2.11 (3)	2.893 (5)	145 (4)
N1—H1···O1A	0.86 (5)	1.97 (5)	2.770 (5)	154 (4)
N21—H21D···O41′	0.88 (5)	1.98 (5)	2.832 (5)	164 (5)
N21—H21C···O1A	0.89 (5)	2.13 (5)	2.885 (5)	143 (4)

Symmetry code: (i) −x+1, −y+1, −z+2.