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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876811202561X/gp5052sup1.cif
Contains datablocks I, II, III, IV, Va, Vb, Vc, Vd, VI, VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052IIsup3.hkl
Contains datablock pk1-31

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052IIIsup4.hkl
Contains datablock mt26-4ohneabs

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052IVsup5.hkl
Contains datablock mt18-11ohneabbs

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052Vasup6.hkl
Contains datablock mt19-8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052Vbsup7.hkl
Contains datablock mt19-12final

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052Vcsup8.hkl
Contains datablock mt19-12afinal

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052Vdsup9.hkl
Contains datablock mt19-10final

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052VIsup10.hkl
Contains datablock mt27-37ohneabs

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876811202561X/gp5052VIIsup11.hkl
Contains datablock mt87-4final

CCDC references: 898997; 898998; 898999; 899000; 899001; 899002; 899003; 899004; 899005; 899006

Computing details top

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) ; top
Crystal data top
C4H4FN3O·C4H5N3Z = 2
Mr = 224.21F(000) = 232
Triclinic, P1Dx = 1.520 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.2414 (12) ÅCell parameters from 2478 reflections
b = 7.2335 (17) Åθ = 3.5–25.7°
c = 11.546 (2) ŵ = 0.12 mm1
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) Å3
Data collection top
STOE IPDS II two-circle-
diffractometer
1246 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.138
Graphite monochromatorθmax = 25.6°, θmin = 3.5°
ω scansh = 77
4298 measured reflectionsk = 88
1834 independent reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.072H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.210 w = 1/[σ2(Fo2) + (0.1395P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
1834 reflectionsΔρmax = 0.32 e Å3
161 parametersΔρmin = 0.38 e Å3
4 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.058 (18)
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.4815 (4)0.2617 (4)0.2068 (2)0.0321 (6)
C20.5522 (5)0.2809 (4)0.3289 (3)0.0314 (7)
N30.4311 (4)0.2225 (4)0.4006 (2)0.0324 (6)
C40.2262 (4)0.1446 (5)0.3452 (3)0.0336 (7)
H40.13740.10420.39310.040*
C50.1372 (5)0.1201 (5)0.2211 (3)0.0361 (7)
H50.00850.06420.18300.043*
C60.2742 (5)0.1820 (5)0.1562 (3)0.0349 (7)
H60.21870.16750.07090.042*
N210.7574 (4)0.3574 (4)0.3848 (2)0.0364 (7)
H21A0.804 (5)0.391 (5)0.4667 (18)0.044*
H21B0.834 (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)
H6'0.27770.16880.67190.041*
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)
H41A0.661 (5)0.320 (5)1.068 (3)0.042*
H41B0.879 (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 (Å2) top
U11U22U33U12U13U23
N10.0289 (12)0.0360 (14)0.0332 (13)0.0014 (10)0.0096 (10)0.0107 (11)
C20.0301 (14)0.0324 (16)0.0353 (16)0.0072 (11)0.0133 (12)0.0105 (13)
N30.0247 (11)0.0412 (15)0.0326 (13)0.0005 (10)0.0091 (9)0.0103 (11)
C40.0255 (13)0.0433 (18)0.0325 (15)0.0002 (12)0.0086 (11)0.0101 (13)
C50.0259 (13)0.0413 (18)0.0363 (16)0.0057 (12)0.0044 (12)0.0056 (14)
C60.0308 (14)0.0394 (17)0.0305 (15)0.0020 (12)0.0036 (12)0.0059 (13)
N210.0220 (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) top
N1—C61.346 (4)N1'—C2'1.380 (4)
N1—C21.356 (4)N1'—H1'0.88 (4)
C2—N211.338 (4)C2'—O21'1.259 (3)
C2—N31.364 (4)C2'—N3'1.369 (4)
N3—C41.338 (4)N3'—C4'1.347 (4)
C4—C51.387 (4)C4'—N41'1.329 (4)
C4—H40.9500C4'—C5'1.419 (4)
C5—C61.383 (4)C5'—C6'1.345 (4)
C5—H50.9500C5'—F51'1.363 (3)
C6—H60.9500C6'—H6'0.9500
N21—H21A0.894 (19)N41'—H41A0.899 (19)
N21—H21B0.879 (19)N41'—H41B0.879 (19)
N1'—C6'1.360 (4)
C6—N1—C2115.8 (2)C6'—N1'—H1'119 (2)
N21—C2—N1118.8 (3)C2'—N1'—H1'119 (2)
N21—C2—N3116.3 (3)O21'—C2'—N3'121.8 (2)
N1—C2—N3124.8 (3)O21'—C2'—N1'118.6 (3)
C4—N3—C2116.6 (3)N3'—C2'—N1'119.6 (2)
N3—C4—C5123.1 (3)C4'—N3'—C2'119.8 (2)
N3—C4—H4118.4N41'—C4'—N3'120.0 (3)
C5—C4—H4118.4N41'—C4'—C5'120.7 (2)
C6—C5—C4115.8 (3)N3'—C4'—C5'119.3 (3)
C6—C5—H5122.1C6'—C5'—F51'120.6 (3)
C4—C5—H5122.1C6'—C5'—C4'121.1 (3)
N1—C6—C5123.8 (3)F51'—C5'—C4'118.3 (3)
N1—C6—H6118.1C5'—C6'—N1'118.2 (3)
C5—C6—H6118.1C5'—C6'—H6'120.9
C2—N21—H21A122 (2)N1'—C6'—H6'120.9
C2—N21—H21B119 (2)C4'—N41'—H41A121 (2)
H21A—N21—H21B116 (3)C4'—N41'—H41B116 (3)
C6'—N1'—C2'121.8 (2)H41A—N41'—H41B123 (3)
C6—N1—C2—N21179.4 (3)N1'—C2'—N3'—C4'4.3 (4)
C6—N1—C2—N31.4 (4)C2'—N3'—C4'—N41'179.2 (3)
N21—C2—N3—C4179.6 (3)C2'—N3'—C4'—C5'1.0 (4)
N1—C2—N3—C41.5 (4)N41'—C4'—C5'—C6'176.6 (3)
C2—N3—C4—C50.8 (4)N3'—C4'—C5'—C6'3.2 (5)
N3—C4—C5—C60.1 (5)N41'—C4'—C5'—F51'1.0 (4)
C2—N1—C6—C50.6 (4)N3'—C4'—C5'—F51'179.1 (2)
C4—C5—C6—N10.0 (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) top
D—H···AD—HH···AD···AD—H···A
N21—H21B···O21i0.88 (2)2.11 (2)2.917 (3)152 (3)
N21—H21A···O210.89 (2)2.20 (2)3.072 (4)165 (3)
N1—H1···N30.88 (4)1.96 (4)2.836 (4)171 (3)
N41—H41B···N3ii0.88 (2)2.09 (2)2.967 (4)173 (3)
N41—H41A···N1iii0.90 (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) ; top
Crystal data top
C6H9N3O2F(000) = 328
Mr = 155.16Dx = 1.399 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2797 reflections
a = 7.9835 (14) Åθ = 3.4–25.8°
b = 10.0664 (12) ŵ = 0.11 mm1
c = 9.8380 (16) ÅT = 173 K
β = 111.266 (13)°Block, colourless
V = 736.8 (2) Å30.40 × 0.20 × 0.20 mm
Z = 4
Data collection top
STOE IPDS II two-circle-
diffractometer
1081 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.075
Graphite monochromatorθmax = 25.6°, θmin = 3.4°
ω scansh = 99
4148 measured reflectionsk = 1212
1378 independent reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 0.97 w = 1/[σ2(Fo2) + (0.0753P)2]
where P = (Fo2 + 2Fc2)/3
1378 reflections(Δ/σ)max < 0.001
107 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.3040 (2)0.43048 (16)0.60310 (15)0.0234 (4)
H10.212 (4)0.481 (2)0.565 (3)0.045 (7)*
C20.4778 (2)0.47782 (19)0.65179 (17)0.0230 (4)
C30.5985 (2)0.35708 (18)0.70209 (19)0.0256 (4)
H3A0.68020.34800.64730.031*
H3B0.67060.36180.80770.031*
N40.46996 (19)0.24849 (15)0.66956 (16)0.0255 (4)
C50.2999 (2)0.29309 (18)0.61126 (17)0.0216 (4)
O210.52338 (16)0.59333 (14)0.65255 (13)0.0310 (4)
C410.5179 (3)0.10924 (19)0.6973 (2)0.0303 (4)
H41A0.63920.10200.77100.046*0.74 (2)
H41B0.51460.06660.60680.046*0.74 (2)
H41C0.43210.06520.73270.046*0.74 (2)
H41D0.41810.05390.63600.046*0.26 (2)
H41E0.54260.08920.80020.046*0.26 (2)
H41F0.62520.09070.67430.046*0.26 (2)
N510.16103 (19)0.21043 (15)0.56779 (15)0.0234 (4)
C520.0100 (2)0.26064 (17)0.53375 (17)0.0221 (4)
C530.1580 (2)0.16038 (18)0.4718 (2)0.0276 (4)
H53A0.18800.12080.55110.041*
H53B0.11790.09060.42110.041*
H53C0.26440.20440.40290.041*
O540.04656 (17)0.37642 (13)0.55588 (15)0.0329 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0179 (8)0.0221 (9)0.0268 (7)0.0029 (6)0.0041 (6)0.0015 (6)
C20.0204 (9)0.0276 (10)0.0202 (8)0.0025 (7)0.0061 (6)0.0007 (6)
C30.0192 (9)0.0271 (11)0.0281 (9)0.0004 (7)0.0056 (7)0.0036 (7)
N40.0181 (7)0.0240 (9)0.0308 (8)0.0021 (6)0.0046 (6)0.0029 (6)
C50.0215 (9)0.0220 (10)0.0208 (8)0.0030 (7)0.0071 (6)0.0004 (6)
O210.0252 (7)0.0282 (8)0.0359 (7)0.0043 (5)0.0067 (5)0.0005 (5)
C410.0227 (9)0.0290 (11)0.0372 (10)0.0060 (8)0.0083 (7)0.0046 (8)
N510.0191 (7)0.0213 (9)0.0278 (7)0.0012 (6)0.0061 (6)0.0010 (6)
C520.0214 (9)0.0222 (10)0.0219 (8)0.0006 (7)0.0067 (7)0.0022 (6)
C530.0206 (9)0.0279 (11)0.0312 (9)0.0022 (7)0.0056 (7)0.0015 (7)
O540.0205 (7)0.0228 (7)0.0521 (8)0.0023 (5)0.0092 (6)0.0013 (6)
Geometric parameters (Å, º) top
N1—C21.378 (2)C41—H41B0.9800
N1—C51.386 (2)C41—H41C0.9800
N1—H10.86 (3)C41—H41D0.9800
C2—O211.218 (2)C41—H41E0.9799
C2—C31.518 (2)C41—H41F0.9800
C3—N41.453 (2)N51—C521.379 (2)
C3—H3A0.9900C52—O541.240 (2)
C3—H3B0.9900C52—C531.504 (2)
N4—C51.345 (2)C53—H53A0.9800
N4—C411.453 (2)C53—H53B0.9800
C5—N511.327 (2)C53—H53C0.9800
C41—H41A0.9800
C2—N1—C5111.50 (14)N4—C41—H41B109.5
C2—N1—H1122.6 (17)N4—C41—H41C109.5
C5—N1—H1125.7 (17)N4—C41—H41D109.5
O21—C2—N1126.41 (16)N4—C41—H41E109.5
O21—C2—C3127.55 (15)H41D—C41—H41E109.5
N1—C2—C3106.05 (15)N4—C41—H41F109.5
N4—C3—C2102.51 (14)H41D—C41—H41F109.5
N4—C3—H3A111.3H41E—C41—H41F109.5
C2—C3—H3A111.3C5—N51—C52119.12 (16)
N4—C3—H3B111.3O54—C52—N51125.27 (16)
C2—C3—H3B111.3O54—C52—C53120.12 (15)
H3A—C3—H3B109.2N51—C52—C53114.55 (15)
C5—N4—C41123.95 (15)C52—C53—H53A109.5
C5—N4—C3111.44 (15)C52—C53—H53B109.5
C41—N4—C3124.60 (14)H53A—C53—H53B109.5
N51—C5—N4121.62 (17)C52—C53—H53C109.5
N51—C5—N1129.88 (15)H53A—C53—H53C109.5
N4—C5—N1108.46 (14)H53B—C53—H53C109.5
N4—C41—H41A109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O54i0.86 (3)2.02 (3)2.849 (2)162 (2)
N1—H1···O540.86 (3)2.29 (2)2.720 (2)111.0 (19)
Symmetry code: (i) x, y+1, z+1.
(III) top
Crystal data top
2(C4H4FN3O)·C6H9N3O2Z = 2
Mr = 413.37F(000) = 428
Triclinic, P1Dx = 1.531 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6548 (12) ÅCell parameters from 4645 reflections
b = 9.3233 (14) Åθ = 3.4–25.8°
c = 12.848 (2) ŵ = 0.13 mm1
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) Å3
Data collection top
STOE IPDS II two-circle-
diffractometer
2293 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.122
Graphite monochromatorθmax = 25.7°, θmin = 3.4°
ω scansh = 99
7962 measured reflectionsk = 1011
3344 independent reflectionsl = 1515
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0933P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3344 reflectionsΔρmax = 0.33 e Å3
286 parametersΔρmin = 0.31 e Å3
6 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (5)
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.8779 (3)0.1895 (2)0.68014 (19)0.0283 (5)
H1A0.851 (4)0.275 (2)0.642 (2)0.034*
C2A0.8488 (4)0.0703 (3)0.6316 (2)0.0272 (6)
N3A0.9005 (3)0.0662 (2)0.67878 (18)0.0284 (5)
C4A0.9784 (4)0.0854 (3)0.7679 (2)0.0254 (6)
C5A1.0118 (4)0.0391 (3)0.8149 (2)0.0283 (6)
C6A0.9609 (4)0.1729 (3)0.7700 (2)0.0278 (6)
H6A0.98240.25600.80050.033*
O21A0.7758 (3)0.0894 (2)0.54864 (16)0.0358 (5)
N41A1.0276 (3)0.2208 (3)0.8109 (2)0.0329 (6)
H4111.068 (4)0.238 (4)0.8742 (18)0.040*
H4120.985 (4)0.287 (3)0.781 (2)0.040*
F51A1.0990 (2)0.01573 (19)0.90320 (14)0.0404 (5)
N1B0.8276 (3)0.7119 (2)0.56716 (18)0.0263 (5)
H1B0.859 (4)0.776 (3)0.606 (2)0.032*
C2B0.8475 (4)0.5737 (3)0.6186 (2)0.0238 (6)
N3B0.8026 (3)0.4628 (2)0.57096 (17)0.0247 (5)
C4B0.7343 (3)0.4869 (3)0.4784 (2)0.0252 (6)
C5B0.7110 (4)0.6329 (3)0.4273 (2)0.0285 (6)
C6B0.7578 (4)0.7424 (3)0.4733 (2)0.0273 (6)
H6B0.74220.83950.44050.033*
O21B0.9087 (3)0.5502 (2)0.70644 (14)0.0270 (4)
N41B0.6909 (3)0.3749 (3)0.4360 (2)0.0305 (6)
H4130.641 (4)0.385 (4)0.3775 (18)0.037*
H4140.704 (4)0.287 (2)0.471 (2)0.037*
F51B0.6411 (3)0.65692 (19)0.33332 (13)0.0422 (5)
N11.2947 (3)0.5685 (2)1.09748 (18)0.0258 (5)
H11.272 (4)0.551 (3)1.163 (3)0.031*
C21.2242 (4)0.4888 (3)1.0123 (2)0.0261 (6)
C31.2933 (4)0.5712 (3)0.9180 (2)0.0296 (6)
H3A1.19500.60050.88490.035*
H3B1.36380.51230.86470.035*
N41.4041 (3)0.6978 (3)0.96428 (18)0.0302 (6)
C51.4010 (4)0.6961 (3)1.0688 (2)0.0264 (6)
O211.1245 (3)0.3734 (2)1.01437 (16)0.0352 (5)
C411.5061 (5)0.8120 (4)0.9051 (3)0.0449 (8)
H41A1.60300.86240.94510.067*
H41B1.55560.76840.83720.067*
H41C1.42850.88190.89330.067*
N511.4814 (3)0.8027 (2)1.13081 (18)0.0296 (5)
C521.5123 (3)0.7770 (3)1.2295 (2)0.0264 (6)
C531.5633 (4)0.9113 (3)1.3020 (2)0.0319 (7)
H53A1.65260.89271.34590.048*
H53B1.61230.99231.26040.048*
H53C1.45810.93661.34720.048*
O541.5066 (3)0.6533 (2)1.25920 (15)0.0307 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0368 (13)0.0159 (11)0.0324 (13)0.0018 (10)0.0070 (10)0.0029 (9)
C2A0.0329 (15)0.0180 (13)0.0313 (15)0.0049 (11)0.0043 (12)0.0024 (11)
N3A0.0375 (13)0.0177 (11)0.0304 (12)0.0030 (10)0.0076 (10)0.0013 (9)
C4A0.0276 (14)0.0203 (13)0.0273 (14)0.0020 (11)0.0017 (11)0.0006 (11)
C5A0.0294 (14)0.0297 (15)0.0269 (14)0.0034 (12)0.0058 (11)0.0058 (12)
C6A0.0312 (14)0.0233 (14)0.0301 (14)0.0041 (11)0.0026 (11)0.0083 (11)
O21A0.0536 (13)0.0215 (10)0.0347 (11)0.0070 (9)0.0159 (10)0.0013 (8)
N41A0.0425 (15)0.0245 (13)0.0326 (13)0.0025 (11)0.0137 (11)0.0009 (11)
F51A0.0510 (11)0.0377 (10)0.0355 (10)0.0024 (8)0.0198 (8)0.0058 (8)
N1B0.0372 (13)0.0149 (11)0.0270 (12)0.0026 (10)0.0037 (10)0.0040 (9)
C2B0.0297 (14)0.0172 (12)0.0238 (13)0.0012 (11)0.0001 (11)0.0047 (10)
N3B0.0324 (12)0.0172 (11)0.0252 (11)0.0027 (9)0.0022 (9)0.0062 (9)
C4B0.0253 (14)0.0226 (13)0.0275 (14)0.0000 (11)0.0023 (11)0.0057 (11)
C5B0.0373 (16)0.0247 (14)0.0239 (14)0.0025 (12)0.0072 (12)0.0023 (11)
C6B0.0362 (15)0.0183 (13)0.0253 (14)0.0003 (11)0.0020 (11)0.0004 (10)
O21B0.0375 (11)0.0202 (9)0.0240 (10)0.0022 (8)0.0072 (8)0.0041 (7)
N41B0.0408 (14)0.0222 (12)0.0307 (13)0.0050 (11)0.0118 (11)0.0032 (10)
F51B0.0656 (12)0.0315 (9)0.0320 (10)0.0044 (9)0.0216 (9)0.0002 (7)
N10.0345 (13)0.0206 (11)0.0218 (11)0.0013 (10)0.0049 (10)0.0050 (9)
C20.0313 (14)0.0234 (14)0.0251 (14)0.0063 (12)0.0059 (11)0.0021 (11)
C30.0335 (15)0.0314 (15)0.0250 (14)0.0070 (12)0.0062 (11)0.0015 (12)
N40.0381 (14)0.0268 (12)0.0252 (12)0.0002 (10)0.0037 (10)0.0063 (10)
C50.0346 (15)0.0222 (14)0.0241 (13)0.0069 (12)0.0029 (11)0.0054 (11)
O210.0428 (12)0.0281 (11)0.0335 (11)0.0031 (10)0.0110 (9)0.0007 (9)
C410.055 (2)0.0449 (19)0.0326 (16)0.0058 (16)0.0009 (15)0.0157 (15)
N510.0402 (14)0.0198 (12)0.0286 (12)0.0019 (10)0.0067 (10)0.0057 (9)
C520.0250 (14)0.0240 (14)0.0300 (14)0.0011 (11)0.0008 (11)0.0069 (11)
C530.0373 (16)0.0249 (15)0.0327 (15)0.0015 (12)0.0068 (12)0.0003 (12)
O540.0385 (11)0.0229 (10)0.0322 (11)0.0023 (9)0.0105 (9)0.0043 (8)
Geometric parameters (Å, º) top
N1A—C6A1.362 (4)C6B—H6B0.9500
N1A—C2A1.392 (3)N41B—H4130.870 (18)
N1A—H1A0.898 (18)N41B—H4140.885 (18)
C2A—O21A1.242 (3)N1—C21.367 (4)
C2A—N3A1.367 (4)N1—C51.398 (4)
N3A—C4A1.332 (4)N1—H10.86 (3)
C4A—N41A1.336 (4)C2—O211.224 (4)
C4A—C5A1.436 (4)C2—C31.512 (4)
C5A—C6A1.335 (4)C3—N41.456 (4)
C5A—F51A1.361 (3)C3—H3A0.9900
C6A—H6A0.9500C3—H3B0.9900
N41A—H4110.891 (18)N4—C51.343 (4)
N41A—H4120.886 (18)N4—C411.458 (4)
N1B—C6B1.357 (4)C5—N511.322 (4)
N1B—C2B1.374 (3)C41—H41A0.9800
N1B—H1B0.898 (18)C41—H41B0.9800
C2B—O21B1.255 (3)C41—H41C0.9800
C2B—N3B1.364 (3)N51—C521.369 (4)
N3B—C4B1.336 (4)C52—O541.249 (3)
C4B—N41B1.331 (3)C52—C531.502 (4)
C4B—C5B1.436 (4)C53—H53A0.9800
C5B—C6B1.348 (4)C53—H53B0.9800
C5B—F51B1.357 (3)C53—H53C0.9800
C6A—N1A—C2A121.8 (2)C4B—N41B—H414120 (2)
C6A—N1A—H1A124 (2)H413—N41B—H414117 (3)
C2A—N1A—H1A113 (2)C2—N1—C5111.3 (2)
O21A—C2A—N3A121.8 (2)C2—N1—H1127 (2)
O21A—C2A—N1A120.1 (2)C5—N1—H1121 (2)
N3A—C2A—N1A118.1 (2)O21—C2—N1125.4 (3)
C4A—N3A—C2A121.3 (2)O21—C2—C3127.9 (3)
N3A—C4A—N41A119.2 (2)N1—C2—C3106.7 (2)
N3A—C4A—C5A119.7 (2)N4—C3—C2102.4 (2)
N41A—C4A—C5A121.1 (3)N4—C3—H3A111.3
C6A—C5A—F51A122.1 (2)C2—C3—H3A111.3
C6A—C5A—C4A119.6 (3)N4—C3—H3B111.3
F51A—C5A—C4A118.3 (2)C2—C3—H3B111.3
C5A—C6A—N1A119.5 (2)H3A—C3—H3B109.2
C5A—C6A—H6A120.2C5—N4—C3111.4 (2)
N1A—C6A—H6A120.2C5—N4—C41124.0 (3)
C4A—N41A—H411122 (2)C3—N4—C41124.6 (2)
C4A—N41A—H412113 (2)N51—C5—N4123.7 (3)
H411—N41A—H412123 (3)N51—C5—N1128.1 (2)
C6B—N1B—C2B122.2 (2)N4—C5—N1108.2 (2)
C6B—N1B—H1B127 (2)N4—C41—H41A109.5
C2B—N1B—H1B111 (2)N4—C41—H41B109.5
O21B—C2B—N3B121.0 (2)H41A—C41—H41B109.5
O21B—C2B—N1B120.5 (2)N4—C41—H41C109.5
N3B—C2B—N1B118.5 (2)H41A—C41—H41C109.5
C4B—N3B—C2B121.5 (2)H41B—C41—H41C109.5
N41B—C4B—N3B119.0 (2)C5—N51—C52119.5 (2)
N41B—C4B—C5B122.1 (2)O54—C52—N51124.6 (3)
N3B—C4B—C5B118.9 (2)O54—C52—C53120.4 (2)
C6B—C5B—F51B121.5 (3)N51—C52—C53114.9 (2)
C6B—C5B—C4B119.8 (3)C52—C53—H53A109.5
F51B—C5B—C4B118.7 (2)C52—C53—H53B109.5
C5B—C6B—N1B119.0 (2)H53A—C53—H53B109.5
C5B—C6B—H6B120.5C52—C53—H53C109.5
N1B—C6B—H6B120.5H53A—C53—H53C109.5
C4B—N41B—H413123 (2)H53B—C53—H53C109.5
C6A—N1A—C2A—O21A178.6 (3)N41B—C4B—C5B—F51B0.6 (4)
C6A—N1A—C2A—N3A2.3 (4)N3B—C4B—C5B—F51B179.8 (2)
O21A—C2A—N3A—C4A179.9 (3)F51B—C5B—C6B—N1B179.8 (3)
N1A—C2A—N3A—C4A0.8 (4)C4B—C5B—C6B—N1B0.5 (4)
C2A—N3A—C4A—N41A179.6 (3)C2B—N1B—C6B—C5B1.9 (4)
C2A—N3A—C4A—C5A1.0 (4)C5—N1—C2—O21179.0 (3)
N3A—C4A—C5A—C6A1.4 (4)C5—N1—C2—C30.9 (3)
N41A—C4A—C5A—C6A180.0 (3)O21—C2—C3—N4179.9 (3)
N3A—C4A—C5A—F51A177.0 (2)N1—C2—C3—N40.2 (3)
N41A—C4A—C5A—F51A1.6 (4)C2—C3—N4—C51.2 (3)
F51A—C5A—C6A—N1A178.4 (3)C2—C3—N4—C41178.6 (3)
C4A—C5A—C6A—N1A0.0 (4)C3—N4—C5—N51175.7 (2)
C2A—N1A—C6A—C5A1.9 (4)C41—N4—C5—N514.5 (5)
C6B—N1B—C2B—O21B178.3 (3)C3—N4—C5—N11.8 (3)
C6B—N1B—C2B—N3B3.0 (4)C41—N4—C5—N1178.0 (3)
O21B—C2B—N3B—C4B178.7 (2)C2—N1—C5—N51175.7 (3)
N1B—C2B—N3B—C4B2.6 (4)C2—N1—C5—N41.7 (3)
C2B—N3B—C4B—N41B179.2 (2)N4—C5—N51—C52162.6 (3)
C2B—N3B—C4B—C5B1.2 (4)N1—C5—N51—C5220.4 (4)
N41B—C4B—C5B—C6B179.7 (3)C5—N51—C52—O5416.6 (4)
N3B—C4B—C5B—C6B0.1 (4)C5—N51—C52—C53166.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N3B0.90 (2)1.88 (2)2.778 (3)175 (3)
N41A—H412···O21Bi0.89 (2)2.07 (2)2.950 (3)175 (3)
N41A—H411···O210.89 (2)2.13 (2)2.946 (3)153 (3)
N1B—H1B···N3Aii0.90 (2)1.91 (2)2.802 (3)171 (3)
N41B—H414···O21A0.89 (2)2.02 (2)2.901 (3)171 (3)
N41B—H413···O54iii0.87 (2)2.02 (2)2.862 (3)162 (3)
N1—H1···O21Biv0.86 (3)2.06 (3)2.817 (3)147 (3)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x1, y+1, z1; (iv) x+2, y, z+2.
(IV) top
Crystal data top
C4H4FN3O·C4H5N3O2F(000) = 1056
Mr = 256.21Dx = 1.650 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9090 reflections
a = 15.5508 (15) Åθ = 3.5–25.9°
b = 11.7839 (7) ŵ = 0.14 mm1
c = 11.4971 (12) ÅT = 173 K
β = 101.660 (8)°Block, colourless
V = 2063.4 (3) Å30.60 × 0.30 × 0.30 mm
Z = 8
Data collection top
STOE IPDS II two-circle-
diffractometer
1507 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.159
Graphite monochromatorθmax = 25.6°, θmin = 3.5°
ω scansh = 1818
15020 measured reflectionsk = 1414
1935 independent reflectionsl = 1312
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0472P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
1935 reflectionsΔρmax = 0.27 e Å3
192 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0018 (5)
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.16314 (8)0.50672 (12)0.75001 (12)0.0208 (3)
H10.1913 (12)0.5430 (16)0.6998 (17)0.027 (5)*
C20.12106 (10)0.57338 (13)0.81866 (14)0.0225 (4)
N30.07348 (8)0.51746 (11)0.88880 (12)0.0210 (3)
H30.0437 (13)0.5558 (18)0.940 (2)0.047 (6)*
C40.06432 (9)0.39869 (13)0.89298 (13)0.0179 (3)
C50.10933 (9)0.33537 (13)0.81943 (13)0.0192 (3)
H50.10490.25500.81760.023*
C60.15942 (9)0.38941 (13)0.75059 (13)0.0177 (3)
O210.12809 (8)0.67801 (10)0.81616 (11)0.0347 (3)
O410.01841 (7)0.35882 (9)0.96112 (10)0.0231 (3)
N610.20757 (9)0.33771 (13)0.68126 (13)0.0242 (3)
H61A0.2167 (15)0.262 (2)0.687 (2)0.061 (7)*
H61B0.2456 (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)
H6'0.40010.65540.32790.028*
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)
H41C0.4458 (14)0.2995 (18)0.4658 (19)0.043 (6)*
H41D0.3913 (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 (Å2) top
U11U22U33U12U13U23
N10.0262 (7)0.0175 (7)0.0238 (7)0.0028 (5)0.0169 (6)0.0003 (5)
C20.0280 (8)0.0178 (8)0.0255 (8)0.0023 (6)0.0146 (7)0.0011 (6)
N30.0266 (7)0.0166 (7)0.0247 (7)0.0002 (5)0.0167 (6)0.0007 (5)
C40.0175 (7)0.0182 (7)0.0198 (8)0.0022 (6)0.0080 (6)0.0010 (6)
C50.0209 (7)0.0146 (7)0.0246 (8)0.0016 (6)0.0106 (6)0.0006 (6)
C60.0177 (7)0.0184 (8)0.0181 (8)0.0009 (6)0.0064 (6)0.0020 (6)
O210.0549 (8)0.0150 (6)0.0445 (7)0.0040 (5)0.0349 (6)0.0002 (5)
O410.0263 (6)0.0204 (6)0.0282 (6)0.0035 (4)0.0189 (5)0.0008 (5)
N610.0268 (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) top
N1—C21.370 (2)N1'—C6'1.366 (2)
N1—C61.384 (2)N1'—C2'1.384 (2)
N1—H10.90 (2)N1'—H1'0.98 (2)
C2—O211.239 (2)C2'—O21'1.2622 (18)
C2—N31.369 (2)C2'—N3'1.3597 (19)
N3—C41.4085 (19)N3'—C4'1.3433 (19)
N3—H30.93 (2)C4'—N41'1.327 (2)
C4—O411.2531 (18)C4'—C5'1.430 (2)
C4—C51.415 (2)C5'—C6'1.346 (2)
C5—C61.374 (2)C5'—F51'1.3569 (18)
C5—H50.9500C6'—H6'0.9500
C6—N611.345 (2)N41'—H41C0.90 (2)
N61—H61A0.90 (2)N41'—H41D0.91 (2)
N61—H61B0.92 (3)
C2—N1—C6123.01 (13)H61A—N61—H61B115 (2)
C2—N1—H1116.7 (12)C6'—N1'—C2'121.93 (14)
C6—N1—H1120.2 (12)C6'—N1'—H1'120.0 (12)
O21—C2—N3123.62 (15)C2'—N1'—H1'117.9 (12)
O21—C2—N1120.18 (14)O21'—C2'—N3'121.60 (14)
N3—C2—N1116.19 (14)O21'—C2'—N1'118.58 (13)
C2—N3—C4124.68 (13)N3'—C2'—N1'119.82 (13)
C2—N3—H3122.2 (13)C4'—N3'—C2'119.78 (13)
C4—N3—H3113.1 (13)N41'—C4'—N3'120.24 (14)
O41—C4—N3117.92 (13)N41'—C4'—C5'119.94 (14)
O41—C4—C5126.10 (14)N3'—C4'—C5'119.81 (13)
N3—C4—C5115.98 (13)C6'—C5'—F51'121.85 (15)
C6—C5—C4120.43 (14)C6'—C5'—C4'120.52 (14)
C6—C5—H5119.8F51'—C5'—C4'117.61 (14)
C4—C5—H5119.8C5'—C6'—N1'118.05 (15)
N61—C6—C5125.44 (15)C5'—C6'—H6'121.0
N61—C6—N1114.90 (14)N1'—C6'—H6'121.0
C5—C6—N1119.66 (14)C4'—N41'—H41C118.9 (14)
C6—N61—H61A120.4 (16)C4'—N41'—H41D119.2 (13)
C6—N61—H61B121.7 (14)H41C—N41'—H41D121.6 (19)
C6—N1—C2—O21178.62 (15)C6'—N1'—C2'—N3'1.9 (2)
C6—N1—C2—N30.5 (2)O21'—C2'—N3'—C4'179.43 (13)
O21—C2—N3—C4179.83 (15)N1'—C2'—N3'—C4'0.3 (2)
N1—C2—N3—C41.1 (2)C2'—N3'—C4'—N41'177.16 (14)
C2—N3—C4—O41179.74 (13)C2'—N3'—C4'—C5'2.8 (2)
C2—N3—C4—C50.9 (2)N41'—C4'—C5'—C6'176.55 (15)
O41—C4—C5—C6178.43 (14)N3'—C4'—C5'—C6'3.4 (2)
N3—C4—C5—C60.9 (2)N41'—C4'—C5'—F51'2.0 (2)
C4—C5—C6—N61177.24 (14)N3'—C4'—C5'—F51'178.07 (13)
C4—C5—C6—N12.4 (2)F51'—C5'—C6'—N1'179.78 (13)
C2—N1—C6—N61177.43 (14)C4'—C5'—C6'—N1'1.3 (2)
C2—N1—C6—C52.2 (2)C2'—N1'—C6'—C5'1.3 (2)
C6'—N1'—C2'—O21'178.42 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O210.90 (2)1.88 (2)2.7805 (17)175.4 (17)
N3—H3···O41i0.93 (2)1.92 (2)2.8534 (17)176.9 (19)
N61—H61A···O21ii0.90 (2)2.62 (2)3.1691 (18)120.6 (18)
N61—H61B···N30.92 (3)2.09 (3)3.011 (2)175.2 (19)
N1—H1···O21iii0.98 (2)1.85 (2)2.8256 (17)173.3 (18)
N41—H41C···O41iv0.90 (2)2.19 (2)2.9012 (17)135.7 (18)
N41—H41D···O21ii0.91 (2)1.91 (2)2.809 (2)169.7 (19)
Symmetry codes: (i) x, y+1, z+2; (ii) x+1/2, y1/2, z+3/2; (iii) x+1/2, y+3/2, z+1; (iv) x+1/2, y+1/2, z1/2.
(Va) ; top
Crystal data top
C4H4FN3O·C4H6N4O·H2OZ = 2
Mr = 273.25F(000) = 284
Triclinic, P1Dx = 1.590 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3280 (12) ÅCell parameters from 4119 reflections
b = 9.3484 (14) Åθ = 4.2–25.8°
c = 9.4779 (15) ŵ = 0.14 mm1
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) Å3
Data collection top
STOE IPDS II two-circle-
diffractometer
1615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.093
Graphite monochromatorθmax = 25.6°, θmin = 4.2°
ω scansh = 1010
6264 measured reflectionsk = 1111
2124 independent reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.0752P)2]
where P = (Fo2 + 2Fc2)/3
2124 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.28 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.4542 (2)0.49058 (18)0.21825 (19)0.0214 (3)
C20.5311 (2)0.3707 (2)0.3352 (2)0.0191 (4)
N30.6523 (2)0.39393 (18)0.38002 (19)0.0186 (3)
H30.710 (3)0.313 (3)0.449 (3)0.024 (5)*
C40.7017 (2)0.5455 (2)0.3086 (2)0.0179 (4)
C50.6179 (2)0.6743 (2)0.1893 (2)0.0209 (4)
H50.64070.78250.13940.025*
C60.5003 (2)0.6412 (2)0.1446 (2)0.0211 (4)
N210.4939 (2)0.2205 (2)0.4120 (2)0.0254 (4)
H21A0.418 (3)0.205 (3)0.379 (3)0.030 (6)*
H21B0.543 (3)0.148 (3)0.485 (3)0.018 (5)*
O410.81837 (17)0.55197 (15)0.35703 (16)0.0230 (3)
N610.4195 (2)0.7584 (2)0.0255 (2)0.0302 (4)
H61A0.359 (4)0.726 (3)0.009 (3)0.046 (7)*
H61B0.462 (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)
H6'1.07510.25740.90630.028*
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)
H41C0.932 (3)0.361 (3)0.531 (3)0.040 (7)*
H41D1.087 (4)0.288 (3)0.624 (3)0.041 (6)*
F51'1.17736 (16)0.00835 (15)0.81322 (16)0.0366 (3)
O1W0.16623 (19)0.49137 (15)0.12840 (17)0.0240 (3)
H1WA0.064 (4)0.517 (3)0.202 (3)0.038 (6)*
H1WB0.252 (4)0.489 (3)0.163 (3)0.033 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0196 (7)0.0248 (8)0.0226 (8)0.0078 (6)0.0099 (6)0.0055 (6)
C20.0153 (8)0.0225 (9)0.0209 (9)0.0031 (6)0.0057 (7)0.0098 (7)
N30.0180 (7)0.0168 (8)0.0230 (8)0.0038 (6)0.0114 (7)0.0046 (6)
C40.0154 (8)0.0200 (9)0.0210 (9)0.0045 (6)0.0046 (7)0.0101 (7)
C50.0206 (9)0.0191 (9)0.0216 (9)0.0073 (7)0.0061 (7)0.0046 (7)
C60.0183 (9)0.0233 (9)0.0186 (9)0.0034 (7)0.0056 (7)0.0066 (7)
N210.0287 (9)0.0203 (8)0.0341 (9)0.0083 (7)0.0201 (8)0.0037 (7)
O410.0239 (7)0.0219 (7)0.0299 (7)0.0076 (5)0.0137 (6)0.0079 (6)
N610.0327 (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)
O1W0.0204 (7)0.0247 (7)0.0278 (7)0.0065 (5)0.0098 (6)0.0072 (6)
Geometric parameters (Å, º) top
N1—C21.332 (2)N1'—C6'1.372 (2)
N1—C61.370 (2)N1'—C2'1.380 (2)
C2—N211.332 (2)N1'—H1'0.87 (3)
C2—N31.368 (2)C2'—O21'1.252 (2)
N3—C41.394 (2)C2'—N3'1.363 (2)
N3—H30.87 (2)N3'—C4'1.342 (2)
C4—O411.270 (2)C4'—N41'1.332 (2)
C4—C51.398 (3)C4'—C5'1.433 (3)
C5—C61.397 (2)C5'—C6'1.340 (3)
C5—H50.9500C5'—F51'1.3607 (19)
C6—N611.356 (2)C6'—H6'0.9500
N21—H21A0.90 (2)N41'—H41C0.90 (3)
N21—H21B0.83 (2)N41'—H41D0.92 (3)
N61—H61A0.90 (3)O1W—H1WA0.87 (3)
N61—H61B0.86 (3)O1W—H1WB0.89 (3)
C2—N1—C6116.85 (15)H61A—N61—H61B117 (2)
N21—C2—N1120.43 (16)C6'—N1'—C2'122.12 (14)
N21—C2—N3117.18 (16)C6'—N1'—H1'121.1 (16)
N1—C2—N3122.38 (15)C2'—N1'—H1'116.4 (16)
C2—N3—C4122.42 (15)O21'—C2'—N3'121.64 (15)
C2—N3—H3122.4 (14)O21'—C2'—N1'118.93 (15)
C4—N3—H3115.0 (14)N3'—C2'—N1'119.43 (15)
O41—C4—N3117.09 (15)C4'—N3'—C2'119.89 (14)
O41—C4—C5126.95 (15)N41'—C4'—N3'119.04 (16)
N3—C4—C5115.96 (15)N41'—C4'—C5'120.99 (16)
C6—C5—C4118.91 (15)N3'—C4'—C5'119.96 (15)
C6—C5—H5120.5C6'—C5'—F51'121.86 (16)
C4—C5—H5120.5C6'—C5'—C4'120.31 (16)
N61—C6—N1114.50 (16)F51'—C5'—C4'117.82 (15)
N61—C6—C5122.10 (16)C5'—C6'—N1'118.18 (16)
N1—C6—C5123.39 (16)C5'—C6'—H6'120.9
C2—N21—H21A116.8 (14)N1'—C6'—H6'120.9
C2—N21—H21B118.8 (13)C4'—N41'—H41C114.3 (15)
H21A—N21—H21B124 (2)C4'—N41'—H41D119.3 (15)
C6—N61—H61A118.2 (16)H41C—N41'—H41D126 (2)
C6—N61—H61B119.6 (18)H1WA—O1W—H1WB104 (2)
C6—N1—C2—N21179.64 (16)C6'—N1'—C2'—N3'3.4 (3)
C6—N1—C2—N30.7 (3)O21'—C2'—N3'—C4'176.12 (16)
N21—C2—N3—C4179.93 (16)N1'—C2'—N3'—C4'3.6 (3)
N1—C2—N3—C41.1 (3)C2'—N3'—C4'—N41'178.83 (17)
C2—N3—C4—O41178.51 (15)C2'—N3'—C4'—C5'1.3 (3)
C2—N3—C4—C50.8 (2)N41'—C4'—C5'—C6'178.44 (18)
O41—C4—C5—C6176.26 (17)N3'—C4'—C5'—C6'1.4 (3)
N3—C4—C5—C63.0 (2)N41'—C4'—C5'—F51'1.1 (3)
C2—N1—C6—N61179.47 (16)N3'—C4'—C5'—F51'179.07 (15)
C2—N1—C6—C51.7 (3)F51'—C5'—C6'—N1'178.81 (16)
C4—C5—C6—N61177.61 (17)C4'—C5'—C6'—N1'1.7 (3)
C4—C5—C6—N13.6 (3)C2'—N1'—C6'—C5'0.7 (3)
C6'—N1'—C2'—O21'176.37 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N30.87 (2)2.05 (3)2.917 (2)176 (2)
N61—H61B···O21i0.86 (3)2.51 (3)3.205 (2)139 (2)
N21—H21A···O21ii0.90 (2)2.05 (2)2.864 (2)150 (2)
N21—H21B···O210.83 (2)2.06 (2)2.887 (2)174.9 (19)
N1—H1···O1Wii0.87 (3)1.99 (3)2.867 (2)177 (2)
N41—H41C···O410.90 (3)2.01 (3)2.906 (2)171 (2)
N41—H41D···O41iii0.92 (3)2.04 (3)2.8441 (19)145 (2)
O1W—H1WA···O41iv0.87 (3)1.95 (3)2.809 (2)170 (2)
O1W—H1WB···N10.89 (3)1.97 (3)2.8661 (19)175 (2)
Symmetry codes: (i) x, y+1, z1; (ii) x+1, y, z+1; (iii) x+2, y+1, z+1; (iv) x1, y, z.
(Vb) ; top
Crystal data top
C4H4FN3O·C4H6N4O·C3H7NOZ = 2
Mr = 328.33F(000) = 344
Triclinic, P1Dx = 1.454 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.0866 (14) ÅCell parameters from 4256 reflections
b = 9.3632 (15) Åθ = 3.4–25.8°
c = 9.4019 (15) ŵ = 0.12 mm1
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) Å3
Data collection top
STOE IPDS II two-circle-
diffractometer
1593 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.080
Graphite monochromatorθmax = 25.6°, θmin = 3.4°
ω scansh = 1111
8452 measured reflectionsk = 1111
2806 independent reflectionsl = 1011
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0457P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.89(Δ/σ)max < 0.001
2806 reflectionsΔρmax = 0.29 e Å3
235 parametersΔρmin = 0.22 e Å3
8 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (3)
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.3660 (2)0.5069 (3)0.8344 (3)0.0261 (5)
C20.4758 (3)0.5363 (3)0.7533 (3)0.0234 (6)
N30.4821 (2)0.6406 (3)0.6742 (2)0.0221 (5)
H30.558 (2)0.656 (3)0.621 (3)0.027*
C40.3748 (3)0.7289 (3)0.6762 (3)0.0231 (6)
C50.2592 (3)0.7008 (3)0.7621 (3)0.0236 (6)
H50.18200.75590.76870.028*
C60.2587 (3)0.5904 (3)0.8384 (3)0.0241 (6)
N210.5867 (3)0.4611 (3)0.7460 (3)0.0340 (6)
H21A0.665 (3)0.484 (4)0.698 (3)0.041*
H21B0.588 (3)0.405 (3)0.809 (3)0.041*
O410.3948 (2)0.8275 (2)0.6039 (2)0.0297 (5)
N610.1525 (3)0.5615 (3)0.9271 (3)0.0369 (7)
H61A0.077 (3)0.608 (3)0.935 (3)0.044*
H61B0.145 (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)
H6'1.07070.78290.31130.030*
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)
H41A0.671 (3)0.991 (3)0.421 (3)0.035*
H41B0.578 (2)0.891 (3)0.506 (3)0.035*
F51'0.90390 (16)0.97161 (18)0.30756 (17)0.0287 (4)
O1A0.0914 (2)0.7263 (2)0.9818 (2)0.0357 (5)
C2A0.1240 (3)0.8222 (3)0.9225 (3)0.0304 (7)
H2A0.05900.85340.85600.036*
N3A0.2422 (2)0.8849 (3)0.9441 (2)0.0269 (5)
C4A0.2661 (3)1.0005 (4)0.8702 (3)0.0364 (7)
H4A10.18451.01930.81010.055*
H4A20.26571.09490.94520.055*
H4A30.36410.96430.80610.055*
C5A0.3518 (3)0.8447 (4)1.0413 (3)0.0334 (7)
H5A10.34170.93131.12880.050*
H5A20.33260.75751.07290.050*
H5A30.45490.81840.98780.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0218 (11)0.0275 (13)0.0376 (13)0.0113 (10)0.0108 (9)0.0179 (11)
C20.0202 (12)0.0198 (15)0.0344 (16)0.0070 (11)0.0064 (11)0.0122 (13)
N30.0187 (11)0.0245 (13)0.0314 (13)0.0096 (10)0.0137 (9)0.0157 (11)
C40.0214 (13)0.0225 (15)0.0297 (15)0.0114 (11)0.0064 (11)0.0091 (13)
C50.0206 (12)0.0233 (15)0.0314 (15)0.0093 (12)0.0085 (11)0.0109 (13)
C60.0171 (12)0.0235 (16)0.0340 (16)0.0035 (11)0.0069 (10)0.0119 (13)
N210.0251 (12)0.0352 (15)0.0588 (18)0.0164 (11)0.0204 (12)0.0314 (14)
O410.0293 (10)0.0296 (12)0.0438 (12)0.0153 (9)0.0152 (9)0.0243 (10)
N610.0307 (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)
O1A0.0327 (10)0.0359 (12)0.0481 (13)0.0156 (10)0.0118 (9)0.0207 (11)
C2A0.0278 (14)0.0300 (16)0.0332 (17)0.0060 (12)0.0083 (12)0.0082 (14)
N3A0.0278 (12)0.0260 (14)0.0304 (13)0.0102 (10)0.0069 (9)0.0099 (11)
C4A0.0367 (16)0.0302 (17)0.0450 (19)0.0083 (14)0.0034 (13)0.0154 (16)
C5A0.0294 (14)0.0418 (18)0.0317 (16)0.0107 (13)0.0087 (12)0.0122 (15)
Geometric parameters (Å, º) top
N1—C21.326 (3)N3'—C4'1.346 (3)
N1—C61.367 (3)C4'—N41'1.331 (3)
C2—N211.341 (3)C4'—C5'1.427 (4)
C2—N31.365 (3)C5'—C6'1.339 (3)
N3—C41.401 (3)C5'—F51'1.366 (3)
N3—H30.889 (17)C6'—H6'0.9500
C4—O411.271 (3)N41'—H41A0.892 (17)
C4—C51.395 (4)N41'—H41B0.889 (17)
C5—C61.400 (4)O1A—C2A1.243 (3)
C5—H50.9500C2A—N3A1.332 (3)
C6—N611.352 (3)C2A—H2A0.9500
N21—H21A0.890 (18)N3A—C5A1.458 (3)
N21—H21B0.883 (17)N3A—C4A1.469 (3)
N61—H61A0.886 (18)C4A—H4A10.9800
N61—H61B0.887 (18)C4A—H4A20.9800
N1'—C6'1.366 (3)C4A—H4A30.9800
N1'—C2'1.370 (3)C5A—H5A10.9800
N1'—H1'0.879 (17)C5A—H5A20.9800
C2'—O21'1.262 (3)C5A—H5A30.9800
C2'—N3'1.360 (3)
C2—N1—C6116.3 (2)N41'—C4'—C5'121.9 (2)
N1—C2—N21119.8 (2)N3'—C4'—C5'119.8 (2)
N1—C2—N3123.0 (2)C6'—C5'—F51'121.5 (2)
N21—C2—N3117.1 (2)C6'—C5'—C4'120.0 (2)
C2—N3—C4122.3 (2)F51'—C5'—C4'118.5 (2)
C2—N3—H3119.5 (17)C5'—C6'—N1'118.7 (2)
C4—N3—H3118.1 (17)C5'—C6'—H6'120.6
O41—C4—C5127.1 (2)N1'—C6'—H6'120.6
O41—C4—N3117.4 (2)C4'—N41'—H41A119.6 (19)
C5—C4—N3115.5 (2)C4'—N41'—H41B120.1 (19)
C4—C5—C6119.0 (2)H41A—N41'—H41B120 (3)
C4—C5—H5120.5O1A—C2A—N3A125.6 (3)
C6—C5—H5120.5O1A—C2A—H2A117.2
N61—C6—N1114.4 (2)N3A—C2A—H2A117.2
N61—C6—C5121.7 (2)C2A—N3A—C5A122.6 (2)
N1—C6—C5123.8 (2)C2A—N3A—C4A120.4 (3)
C2—N21—H21A121 (2)C5A—N3A—C4A117.0 (2)
C2—N21—H21B115 (2)N3A—C4A—H4A1109.5
H21A—N21—H21B122 (3)N3A—C4A—H4A2109.5
C6—N61—H61A121 (2)H4A1—C4A—H4A2109.5
C6—N61—H61B122 (2)N3A—C4A—H4A3109.5
H61A—N61—H61B116 (3)H4A1—C4A—H4A3109.5
C6'—N1'—C2'121.8 (2)H4A2—C4A—H4A3109.5
C6'—N1'—H1'119.1 (19)N3A—C5A—H5A1109.5
C2'—N1'—H1'119.0 (19)N3A—C5A—H5A2109.5
O21'—C2'—N3'121.0 (2)H5A1—C5A—H5A2109.5
O21'—C2'—N1'119.3 (2)N3A—C5A—H5A3109.5
N3'—C2'—N1'119.8 (2)H5A1—C5A—H5A3109.5
C4'—N3'—C2'119.8 (2)H5A2—C5A—H5A3109.5
N41'—C4'—N3'118.3 (2)
C6—N1—C2—N21178.8 (3)O21'—C2'—N3'—C4'178.6 (3)
C6—N1—C2—N31.6 (4)N1'—C2'—N3'—C4'1.0 (4)
N1—C2—N3—C42.1 (4)C2'—N3'—C4'—N41'179.4 (2)
N21—C2—N3—C4178.3 (3)C2'—N3'—C4'—C5'0.5 (4)
C2—N3—C4—O41176.9 (3)N41'—C4'—C5'—C6'177.5 (3)
C2—N3—C4—C51.3 (4)N3'—C4'—C5'—C6'2.3 (4)
O41—C4—C5—C6177.8 (3)N41'—C4'—C5'—F51'2.0 (4)
N3—C4—C5—C60.2 (4)N3'—C4'—C5'—F51'178.2 (2)
C2—N1—C6—N61177.4 (3)F51'—C5'—C6'—N1'177.9 (2)
C2—N1—C6—C50.6 (4)C4'—C5'—C6'—N1'2.6 (4)
C4—C5—C6—N61177.9 (3)C2'—N1'—C6'—C5'1.2 (4)
C4—C5—C6—N10.1 (4)O1A—C2A—N3A—C5A1.0 (4)
C6'—N1'—C2'—O21'179.0 (3)O1A—C2A—N3A—C4A178.3 (3)
C6'—N1'—C2'—N3'0.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N30.89 (2)2.06 (2)2.941 (3)170 (3)
N61—H61A···O1A0.89 (2)2.08 (2)2.958 (3)173 (3)
N61—H61B···O1Ai0.89 (2)2.12 (2)2.988 (3)167 (3)
N21—H21A···O210.89 (2)2.01 (2)2.898 (3)179 (3)
N1—H1···O21ii0.88 (2)1.87 (2)2.748 (3)174 (3)
N41—H41B···O410.89 (2)2.02 (2)2.904 (3)177 (3)
N41—H41A···O41iii0.89 (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) ; top
Crystal data top
2(C4H4FN3O)·2(C4H6N4O)·C3H7NOZ = 1
Mr = 583.56F(000) = 304
Triclinic, P1Dx = 1.463 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1894 (12) ÅCell parameters from 3942 reflections
b = 10.0991 (15) Åθ = 3.7–25.8°
c = 10.9953 (19) ŵ = 0.12 mm1
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) Å3
Data collection top
STOE IPDS II two-circle-
diffractometer
1665 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.074
Graphite monochromatorθmax = 25.6°, θmin = 3.5°
ω scansh = 88
7507 measured reflectionsk = 1212
2475 independent reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0889P)2 + 0.0624P]
where P = (Fo2 + 2Fc2)/3
2475 reflections(Δ/σ)max < 0.001
242 parametersΔρmax = 0.29 e Å3
11 restraintsΔρmin = 0.23 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.8427 (4)0.5383 (3)0.8547 (3)0.0226 (6)
C20.8119 (4)0.6116 (3)0.7732 (3)0.0192 (6)
N30.6191 (4)0.6122 (3)0.7173 (3)0.0213 (6)
H30.603 (6)0.663 (4)0.661 (4)0.042 (10)*
C40.4361 (5)0.5313 (3)0.7384 (3)0.0222 (7)
C50.4643 (5)0.4485 (3)0.8206 (3)0.0237 (7)
H50.34580.38750.83700.028*
C60.6672 (5)0.4564 (3)0.8779 (3)0.0216 (6)
N210.9765 (4)0.6913 (3)0.7435 (3)0.0270 (6)
H21A0.952 (6)0.743 (4)0.691 (4)0.032 (9)*
H21B1.087 (6)0.674 (4)0.758 (4)0.029 (9)*
O410.2645 (3)0.5405 (3)0.6839 (2)0.0290 (6)
N610.7038 (4)0.3807 (3)0.9595 (3)0.0295 (7)
H61A0.600 (5)0.344 (4)0.991 (4)0.038 (10)*
H61B0.841 (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)
H6'0.49780.94460.27670.028*
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)
H41A0.054 (6)0.622 (4)0.415 (4)0.028 (9)*
H41B0.216 (6)0.620 (4)0.540 (4)0.037 (10)*
F51'0.1330 (3)0.7845 (2)0.2814 (2)0.0328 (5)
O1A0.3541 (13)0.1276 (10)0.9696 (11)0.097 (3)0.50
C2A0.1657 (17)0.1064 (10)0.9424 (10)0.062 (3)0.50
H2A0.11140.15010.88360.075*0.50
N3A0.0349 (16)0.0273 (10)0.9892 (10)0.049 (2)0.50
C5A0.093 (3)0.0374 (14)1.0876 (12)0.074 (4)0.50
H5A10.25050.00491.12930.110*0.50
H5A20.02750.14961.04110.110*0.50
H5A30.03880.01151.15890.110*0.50
C4A0.1900 (19)0.0065 (17)0.9477 (16)0.086 (4)0.50
H4A10.19960.08720.91640.129*0.50
H4A20.23200.01311.02610.129*0.50
H4A30.28760.09460.87310.129*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0199 (12)0.0259 (13)0.0256 (15)0.0111 (11)0.0079 (11)0.0156 (12)
C20.0200 (14)0.0190 (14)0.0209 (16)0.0105 (12)0.0080 (12)0.0089 (13)
N30.0200 (13)0.0261 (13)0.0268 (15)0.0128 (11)0.0105 (11)0.0191 (12)
C40.0192 (14)0.0260 (15)0.0217 (17)0.0102 (12)0.0085 (13)0.0094 (14)
C50.0225 (15)0.0278 (16)0.0253 (18)0.0114 (13)0.0103 (13)0.0163 (14)
C60.0257 (15)0.0220 (15)0.0213 (17)0.0130 (13)0.0106 (13)0.0102 (13)
N210.0208 (14)0.0357 (15)0.0374 (18)0.0165 (12)0.0138 (12)0.0259 (14)
O410.0203 (11)0.0388 (13)0.0394 (15)0.0166 (10)0.0133 (10)0.0263 (12)
N610.0266 (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)
O1A0.071 (5)0.083 (6)0.124 (8)0.011 (4)0.033 (5)0.060 (6)
C2A0.085 (8)0.046 (5)0.049 (6)0.020 (5)0.020 (6)0.028 (5)
N3A0.074 (7)0.042 (7)0.028 (4)0.026 (6)0.013 (4)0.016 (4)
C5A0.151 (14)0.061 (7)0.044 (7)0.072 (9)0.038 (8)0.038 (6)
C4A0.075 (9)0.073 (8)0.061 (10)0.020 (7)0.002 (6)0.003 (7)
Geometric parameters (Å, º) top
N1—C21.324 (4)N3'—C4'1.344 (4)
N1—C61.371 (4)C4'—N41'1.330 (4)
C2—N211.348 (4)C4'—C5'1.434 (4)
C2—N31.363 (3)C5'—C6'1.341 (4)
N3—C41.396 (4)C5'—F51'1.361 (3)
N3—H30.91 (4)C6'—H6'0.9500
C4—O411.269 (3)N41'—H41A0.90 (4)
C4—C51.404 (4)N41'—H41B0.91 (4)
C5—C61.391 (4)O1A—C2A1.231 (11)
C5—H50.9500C2A—N3A1.311 (10)
C6—N611.353 (4)C2A—H2A0.9500
N21—H21A0.90 (4)N3A—C5A1.446 (10)
N21—H21B0.85 (4)N3A—C4A1.478 (14)
N61—H61A0.902 (19)C5A—H5A10.9800
N61—H61B0.883 (19)C5A—H5A20.9800
N1'—C6'1.366 (4)C5A—H5A30.9800
N1'—C2'1.383 (4)C4A—H4A10.9800
N1'—H1'0.89 (2)C4A—H4A20.9800
C2'—O21'1.256 (4)C4A—H4A30.9800
C2'—N3'1.361 (4)
C2—N1—C6116.8 (2)C2'—N1'—H1'118 (3)
N1—C2—N21119.8 (2)O21'—C2'—N3'121.2 (2)
N1—C2—N3123.0 (2)O21'—C2'—N1'119.1 (2)
N21—C2—N3117.2 (2)N3'—C2'—N1'119.6 (2)
C2—N3—C4122.3 (2)C4'—N3'—C2'120.2 (2)
C2—N3—H3121 (2)N41'—C4'—N3'119.1 (3)
C4—N3—H3117 (2)N41'—C4'—C5'121.2 (3)
O41—C4—N3117.9 (2)N3'—C4'—C5'119.7 (2)
O41—C4—C5126.8 (3)C6'—C5'—F51'122.1 (2)
N3—C4—C5115.3 (2)C6'—C5'—C4'119.9 (3)
C6—C5—C4119.5 (3)F51'—C5'—C4'118.0 (2)
C6—C5—H5120.2C5'—C6'—N1'119.1 (3)
C4—C5—H5120.2C5'—C6'—H6'120.4
N61—C6—N1115.1 (2)N1'—C6'—H6'120.4
N61—C6—C5121.9 (3)C4'—N41'—H41A121 (2)
N1—C6—C5123.0 (2)C4'—N41'—H41B115 (2)
C2—N21—H21A118 (2)H41A—N41'—H41B119 (3)
C2—N21—H21B119 (2)O1A—C2A—N3A124.3 (9)
H21A—N21—H21B122 (3)O1A—C2A—H2A117.8
C6—N61—H61A116 (2)N3A—C2A—H2A117.8
C6—N61—H61B115 (3)C2A—N3A—C5A125.8 (10)
H61A—N61—H61B123 (4)C2A—N3A—C4A119.8 (10)
C6'—N1'—C2'121.4 (2)C5A—N3A—C4A114.2 (8)
C6'—N1'—H1'120 (3)
C6—N1—C2—N21178.4 (3)O21'—C2'—N3'—C4'178.7 (3)
C6—N1—C2—N32.2 (4)N1'—C2'—N3'—C4'1.2 (4)
N1—C2—N3—C42.0 (5)C2'—N3'—C4'—N41'178.3 (3)
N21—C2—N3—C4178.6 (3)C2'—N3'—C4'—C5'0.2 (4)
C2—N3—C4—O41178.9 (3)N41'—C4'—C5'—C6'177.2 (3)
C2—N3—C4—C50.4 (4)N3'—C4'—C5'—C6'1.2 (4)
O41—C4—C5—C6177.0 (3)N41'—C4'—C5'—F51'1.9 (4)
N3—C4—C5—C62.3 (4)N3'—C4'—C5'—F51'179.7 (3)
C2—N1—C6—N61178.8 (3)F51'—C5'—C6'—N1'179.9 (3)
C2—N1—C6—C50.2 (4)C4'—C5'—C6'—N1'0.8 (4)
C4—C5—C6—N61179.0 (3)C2'—N1'—C6'—C5'0.6 (5)
C4—C5—C6—N12.1 (5)O1A—C2A—N3A—C5A5.1 (19)
C6'—N1'—C2'—O21'178.3 (3)O1A—C2A—N3A—C4A178.8 (12)
C6'—N1'—C2'—N3'1.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···N30.91 (4)2.00 (4)2.907 (3)178 (3)
N61—H61B···N1i0.88 (2)2.16 (2)3.031 (4)169 (4)
N61—H61A···O1A0.90 (2)2.17 (3)2.931 (8)141 (3)
N21—H21B···O41ii0.85 (4)2.31 (4)3.080 (3)150 (3)
N21—H21A···O210.90 (4)2.03 (4)2.932 (3)175 (3)
N1—H1···O21iii0.89 (2)1.85 (2)2.742 (3)179 (5)
N41—H41B···O410.91 (4)1.96 (4)2.863 (3)172 (3)
N41—H41A···O41iv0.90 (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) ; top
Crystal data top
2(C4H4FN3O)·C4H6N4O·C3H7NOZ = 6
Mr = 457.43F(000) = 1428
Triclinic, P1Dx = 1.501 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.2283 (11) ÅCell parameters from 11994 reflections
b = 15.1837 (12) Åθ = 3.4–25.7°
c = 18.8290 (17) ŵ = 0.13 mm1
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) Å3
Data collection top
STOE IPDS II two-circle-
diffractometer
5218 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.097
Graphite monochromatorθmax = 25.0°, θmin = 3.4°
ω scansh = 1313
32977 measured reflectionsk = 1818
10672 independent reflectionsl = 2218
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 0.90 w = 1/[σ2(Fo2) + (0.0533P)2]
where P = (Fo2 + 2Fc2)/3
10672 reflections(Δ/σ)max = 0.001
981 parametersΔρmax = 0.62 e Å3
33 restraintsΔρmin = 0.34 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.0441 (3)0.5768 (2)0.55522 (19)0.0254 (8)
C2A0.0027 (3)0.6429 (2)0.4964 (2)0.0215 (9)
N3A0.0053 (3)0.7348 (2)0.4930 (2)0.0249 (8)
H3A0.042 (4)0.775 (3)0.455 (2)0.030*
C4A0.0462 (3)0.7650 (2)0.5502 (2)0.0229 (9)
C5A0.0992 (4)0.6971 (3)0.6109 (2)0.0263 (9)
H5A0.13830.71360.65080.032*
C6A0.0944 (3)0.6038 (3)0.6125 (2)0.0231 (9)
N21A0.0548 (3)0.6212 (2)0.4385 (2)0.0260 (8)
H21A0.053 (3)0.5635 (15)0.440 (2)0.031*
H21B0.090 (3)0.662 (2)0.3995 (16)0.031*
O41A0.0372 (3)0.85096 (17)0.54260 (16)0.0333 (7)
N61A0.1358 (3)0.5337 (2)0.6720 (2)0.0343 (9)
H61A0.121 (4)0.4760 (16)0.676 (2)0.041*
H61B0.183 (3)0.541 (3)0.7094 (18)0.041*
N1B0.2222 (3)0.9053 (2)0.24467 (19)0.0257 (8)
H1B0.257 (3)0.883 (3)0.2116 (18)0.031*
C2B0.1733 (3)0.8403 (3)0.3076 (2)0.0223 (9)
N3B0.1223 (3)0.8689 (2)0.36472 (18)0.0224 (7)
C4B0.1246 (3)0.9593 (3)0.3592 (2)0.0238 (9)
C5B0.1785 (4)1.0249 (3)0.2933 (2)0.0286 (10)
C6B0.2253 (4)0.9973 (3)0.2376 (2)0.0293 (9)
H6B0.26021.04090.19380.035*
O21B0.1756 (2)0.75601 (17)0.31108 (15)0.0293 (7)
N41B0.0756 (3)0.9858 (2)0.4145 (2)0.0305 (8)
H41A0.042 (3)0.947 (2)0.4561 (16)0.037*
H41B0.069 (4)1.0429 (16)0.413 (2)0.037*
F51B0.1780 (2)1.11572 (15)0.29117 (14)0.0415 (6)
N1C0.4658 (3)0.8843 (2)0.0264 (2)0.0297 (8)
H1C0.513 (4)0.924 (3)0.005 (3)0.036*
C2C0.3913 (4)0.9083 (3)0.0782 (2)0.0293 (10)
N3C0.3337 (3)0.8400 (2)0.13371 (19)0.0264 (8)
C4C0.3487 (3)0.7496 (3)0.1380 (2)0.0251 (9)
C5C0.4232 (4)0.7275 (3)0.0822 (2)0.0303 (10)
C6C0.4808 (4)0.7945 (3)0.0289 (2)0.0292 (10)
H6C0.53220.77940.00720.035*
O21C0.3769 (3)0.99239 (18)0.07300 (16)0.0366 (7)
N41C0.2942 (3)0.6839 (2)0.1935 (2)0.0330 (9)
H41C0.308 (4)0.6252 (16)0.197 (2)0.040*
H41D0.248 (3)0.705 (3)0.2250 (19)0.040*
F51C0.4374 (2)0.63690 (16)0.08649 (16)0.0448 (7)
O1X0.2789 (3)0.5192 (2)0.80670 (18)0.0482 (9)
N3X0.3413 (3)0.6308 (2)0.8579 (2)0.0351 (9)
C2X0.3244 (5)0.5407 (3)0.8584 (3)0.0286 (14)0.771 (7)
H2X10.35000.49210.90210.034*0.771 (7)
C4X0.3906 (5)0.6531 (4)0.9202 (4)0.0463 (19)0.771 (7)
H4X10.39520.72080.90810.070*0.771 (7)
H4X20.34010.62680.96310.070*0.771 (7)
H4X30.47080.62710.93280.070*0.771 (7)
C5X0.3062 (5)0.7056 (3)0.7886 (3)0.0326 (15)0.771 (7)
H5X10.32300.76610.79550.049*0.771 (7)
H5X20.35160.70050.74700.049*0.771 (7)
H5X30.22080.70010.77730.049*0.771 (7)
C2X'0.291 (2)0.6024 (8)0.8061 (10)0.090 (10)*0.229 (7)
H2X20.26060.64900.76270.109*0.229 (7)
C4X'0.358 (3)0.7282 (8)0.8569 (14)0.085 (9)*0.229 (7)
H4X40.40390.72920.90240.128*0.229 (7)
H4X50.40200.76330.81260.128*0.229 (7)
H4X60.28040.75660.85510.128*0.229 (7)
C5X'0.3944 (17)0.5692 (10)0.9300 (7)0.047 (6)*0.229 (7)
H5X40.43100.60720.95870.071*0.229 (7)
H5X50.33190.52930.95910.071*0.229 (7)
H5X60.45530.53030.91970.071*0.229 (7)
N1D0.7028 (3)0.7928 (2)0.12640 (18)0.0215 (7)
C2D0.6528 (3)0.7259 (2)0.1847 (2)0.0196 (8)
N3D0.6623 (3)0.6342 (2)0.19134 (19)0.0247 (8)
H3D0.615 (3)0.596 (2)0.2277 (17)0.030*
C4D0.7237 (3)0.6024 (3)0.1381 (2)0.0243 (9)
C5D0.7777 (3)0.6705 (2)0.0767 (2)0.0239 (9)
H5D0.82380.65370.03930.029*
C6D0.7617 (3)0.7633 (2)0.0722 (2)0.0219 (8)
N21D0.5915 (3)0.7493 (2)0.23889 (19)0.0255 (8)
H21C0.546 (4)0.708 (3)0.271 (2)0.031*
H21D0.581 (3)0.807 (3)0.237 (2)0.031*
O41D0.7245 (3)0.51477 (17)0.14974 (16)0.0348 (7)
N61D0.8064 (3)0.8330 (2)0.0121 (2)0.0306 (8)
H61C0.774 (3)0.8885 (18)0.009 (2)0.037*
H61D0.840 (3)0.820 (3)0.0279 (16)0.037*
N1E0.3985 (3)0.4703 (2)0.42283 (19)0.0269 (8)
H1E0.361 (3)0.492 (3)0.4561 (18)0.032*
C2E0.4600 (3)0.5345 (2)0.3650 (2)0.0214 (8)
N3E0.5166 (3)0.5069 (2)0.30935 (19)0.0240 (7)
C4E0.5088 (3)0.4180 (3)0.3117 (2)0.0227 (9)
C5E0.4438 (4)0.3530 (3)0.3708 (2)0.0299 (10)
C6E0.3897 (4)0.3800 (3)0.4264 (2)0.0311 (10)
H6E0.34670.33680.46690.037*
O21E0.4632 (2)0.61780 (17)0.36430 (16)0.0318 (7)
N41E0.5654 (3)0.3912 (2)0.2571 (2)0.0295 (8)
H41E0.572 (4)0.3310 (15)0.263 (2)0.035*
H41F0.611 (3)0.431 (2)0.2220 (18)0.035*
F51E0.4403 (2)0.26290 (15)0.37137 (15)0.0474 (7)
N1F0.1815 (3)0.4775 (2)0.65690 (19)0.0270 (8)
H1F0.143 (3)0.434 (2)0.6934 (18)0.032*
C2F0.2345 (3)0.4566 (3)0.5962 (2)0.0235 (9)
N3F0.2898 (3)0.5255 (2)0.53908 (18)0.0228 (7)
C4F0.2904 (3)0.6123 (3)0.5421 (2)0.0247 (9)
C5F0.2371 (4)0.6321 (3)0.6056 (2)0.0287 (9)
C6F0.1832 (4)0.5648 (3)0.6615 (2)0.0301 (10)
H6F0.14680.57810.70360.036*
O21F0.2317 (2)0.37445 (17)0.59444 (16)0.0296 (7)
N41F0.3398 (3)0.6803 (2)0.4851 (2)0.0300 (8)
H41G0.349 (3)0.7381 (16)0.484 (2)0.036*
H41H0.377 (3)0.662 (3)0.4499 (18)0.036*
F51F0.2428 (2)0.72039 (15)0.60862 (14)0.0441 (7)
N1G0.4246 (3)0.0488 (2)1.22579 (18)0.0243 (7)
C2G0.3682 (3)0.0157 (2)1.1701 (2)0.0206 (8)
N3G0.3612 (3)0.1065 (2)1.16810 (19)0.0235 (7)
H3G0.311 (3)0.143 (2)1.1352 (18)0.028*
C4G0.4129 (3)0.1379 (3)1.2248 (2)0.0245 (9)
C5G0.4748 (3)0.0718 (2)1.2826 (2)0.0263 (9)
H5G0.51460.08881.32200.032*
C6G0.4779 (3)0.0209 (3)1.2821 (2)0.0246 (9)
N21G0.3147 (3)0.0071 (2)1.11295 (19)0.0247 (8)
H21E0.267 (4)0.037 (3)1.080 (2)0.030*
H21F0.312 (3)0.067 (3)1.119 (2)0.030*
O41G0.3985 (2)0.22271 (17)1.21802 (16)0.0297 (7)
N61G0.5301 (3)0.0897 (2)1.3384 (2)0.0354 (9)
H61E0.536 (4)0.145 (3)1.336 (3)0.043*
H61F0.563 (4)0.078 (3)1.378 (3)0.043*
N1H0.0889 (3)0.2675 (2)0.94391 (19)0.0231 (7)
H1H0.063 (3)0.247 (3)0.9075 (17)0.028*
C2H0.1462 (3)0.2056 (2)1.0053 (2)0.0197 (8)
N3H0.2103 (3)0.2371 (2)1.05526 (18)0.0208 (7)
C4H0.2096 (3)0.3296 (2)1.0474 (2)0.0233 (9)
C5H0.1428 (4)0.3904 (2)0.9868 (2)0.0259 (9)
C6H0.0863 (3)0.3595 (2)0.9354 (2)0.0244 (9)
H6H0.04490.40140.89340.029*
O21H0.1398 (2)0.11947 (16)1.01315 (15)0.0270 (6)
N41H0.2748 (3)0.3588 (2)1.0970 (2)0.0263 (8)
H41I0.310 (3)0.318 (2)1.1376 (16)0.032*
H41J0.270 (3)0.4188 (15)1.091 (2)0.032*
F51H0.1417 (2)0.48298 (14)0.98242 (14)0.0364 (6)
N1I0.1164 (3)0.2437 (2)0.71342 (19)0.0253 (7)
H1I0.152 (3)0.281 (2)0.6739 (16)0.030*
C2I0.0493 (3)0.2689 (2)0.7675 (2)0.0220 (8)
N3I0.0062 (3)0.20124 (19)0.82967 (17)0.0205 (7)
C4I0.0278 (3)0.1110 (2)0.8378 (2)0.0229 (8)
C5I0.0937 (3)0.0872 (3)0.7802 (2)0.0254 (9)
C6I0.1375 (3)0.1527 (3)0.7203 (2)0.0239 (9)
H6I0.18330.13630.68250.029*
O21I0.0313 (2)0.35301 (16)0.75957 (15)0.0290 (6)
N41I0.0149 (3)0.0463 (2)0.9004 (2)0.0288 (8)
H41K0.010 (3)0.0120 (16)0.913 (2)0.035*
H41L0.056 (3)0.065 (3)0.9357 (18)0.035*
F51I0.1104 (2)0.00583 (13)0.78849 (13)0.0335 (6)
O1Y0.9097 (3)0.7515 (2)0.09598 (17)0.0431 (8)
C2Y0.9754 (4)0.7810 (3)0.1511 (3)0.0320 (10)
H2Y0.99470.84510.16610.038*
N3Y1.0233 (3)0.7312 (2)0.19309 (19)0.0269 (7)
C5Y1.0016 (4)0.6321 (3)0.1744 (3)0.0371 (11)
H5Y10.95010.61110.12870.056*
H5Y21.07760.59780.16610.056*
H5Y30.96230.62050.21590.056*
C4Y1.0994 (4)0.7756 (3)0.2594 (3)0.0456 (12)
H4Y11.10660.84180.26550.068*
H4Y21.06420.76870.30390.068*
H4Y31.17860.74610.25340.068*
O1Z0.6507 (3)0.1135 (2)1.48097 (18)0.0461 (8)
C2Z0.6969 (4)0.0844 (3)1.5309 (3)0.0430 (12)
H2Z0.73290.12921.57350.052*
N3Z0.7005 (3)0.0030 (2)1.52978 (19)0.0309 (8)
C4Z0.7581 (4)0.0302 (3)1.5903 (3)0.0432 (12)
H4Z10.78920.02521.62930.065*
H4Z20.82390.07351.57080.065*
H4Z30.70010.06041.61180.065*
C5Z0.6522 (5)0.0764 (3)1.4661 (3)0.0566 (14)
H5Z10.62610.05081.42630.085*
H5Z20.58410.10411.48130.085*
H5Z30.71370.12431.44750.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.038 (2)0.0166 (16)0.0202 (19)0.0031 (14)0.0044 (15)0.0053 (15)
C2A0.031 (2)0.0162 (18)0.019 (2)0.0015 (16)0.0017 (18)0.0071 (18)
N3A0.038 (2)0.0159 (17)0.0192 (19)0.0032 (14)0.0094 (15)0.0051 (15)
C4A0.034 (2)0.0152 (19)0.021 (2)0.0021 (16)0.0047 (18)0.0079 (17)
C5A0.036 (2)0.020 (2)0.025 (2)0.0019 (17)0.0029 (18)0.0104 (18)
C6A0.026 (2)0.022 (2)0.022 (2)0.0025 (16)0.0036 (17)0.0099 (19)
N21A0.040 (2)0.0159 (17)0.023 (2)0.0060 (15)0.0074 (16)0.0083 (16)
O41A0.0553 (19)0.0151 (14)0.0301 (17)0.0033 (13)0.0113 (14)0.0099 (13)
N61A0.055 (2)0.0209 (18)0.025 (2)0.0049 (16)0.0186 (17)0.0070 (17)
N1B0.037 (2)0.0212 (17)0.0176 (18)0.0051 (14)0.0086 (15)0.0059 (15)
C2B0.024 (2)0.023 (2)0.021 (2)0.0009 (16)0.0018 (17)0.0096 (18)
N3B0.0303 (18)0.0172 (16)0.0196 (18)0.0016 (13)0.0030 (14)0.0063 (15)
C4B0.027 (2)0.023 (2)0.021 (2)0.0039 (16)0.0009 (18)0.0066 (18)
C5B0.040 (2)0.0158 (19)0.029 (2)0.0022 (17)0.004 (2)0.0068 (19)
C6B0.038 (2)0.018 (2)0.029 (2)0.0059 (17)0.0060 (19)0.0035 (18)
O21B0.0467 (17)0.0188 (14)0.0223 (16)0.0067 (12)0.0077 (13)0.0073 (12)
N41B0.048 (2)0.0173 (17)0.028 (2)0.0050 (16)0.0079 (17)0.0099 (16)
F51B0.0650 (17)0.0154 (12)0.0426 (16)0.0054 (11)0.0122 (13)0.0090 (11)
N1C0.035 (2)0.030 (2)0.022 (2)0.0033 (15)0.0083 (15)0.0057 (16)
C2C0.036 (2)0.025 (2)0.020 (2)0.0056 (18)0.0049 (19)0.0010 (19)
N3C0.0317 (18)0.0232 (17)0.0219 (19)0.0003 (14)0.0042 (15)0.0045 (15)
C4C0.027 (2)0.026 (2)0.023 (2)0.0002 (17)0.0013 (18)0.0092 (19)
C5C0.034 (2)0.029 (2)0.035 (3)0.0012 (19)0.002 (2)0.019 (2)
C6C0.032 (2)0.033 (2)0.026 (2)0.0002 (19)0.0028 (19)0.014 (2)
O21C0.0489 (18)0.0218 (15)0.0353 (18)0.0042 (13)0.0145 (14)0.0062 (13)
N41C0.041 (2)0.0241 (19)0.036 (2)0.0035 (16)0.0098 (18)0.0135 (18)
F51C0.0547 (16)0.0291 (13)0.0572 (18)0.0091 (11)0.0175 (13)0.0252 (13)
O1X0.057 (2)0.050 (2)0.038 (2)0.0062 (16)0.0162 (16)0.0168 (17)
N3X0.035 (2)0.0255 (18)0.039 (2)0.0063 (15)0.0009 (17)0.0015 (18)
C2X0.044 (3)0.017 (3)0.026 (3)0.009 (2)0.009 (3)0.009 (2)
C4X0.047 (4)0.053 (4)0.056 (4)0.002 (3)0.005 (3)0.043 (4)
C5X0.032 (3)0.018 (3)0.042 (4)0.003 (2)0.004 (3)0.002 (3)
N1D0.0289 (17)0.0182 (16)0.0190 (18)0.0012 (13)0.0048 (14)0.0088 (14)
C2D0.025 (2)0.0142 (18)0.019 (2)0.0026 (15)0.0014 (17)0.0055 (17)
N3D0.037 (2)0.0151 (16)0.0217 (19)0.0004 (14)0.0078 (15)0.0074 (15)
C4D0.031 (2)0.024 (2)0.022 (2)0.0007 (16)0.0027 (18)0.0138 (18)
C5D0.033 (2)0.0195 (19)0.021 (2)0.0015 (16)0.0070 (18)0.0098 (18)
C6D0.027 (2)0.0189 (19)0.019 (2)0.0026 (16)0.0048 (17)0.0046 (17)
N21D0.040 (2)0.0119 (16)0.026 (2)0.0047 (14)0.0152 (16)0.0093 (15)
O41D0.0560 (19)0.0121 (14)0.0359 (18)0.0045 (12)0.0134 (14)0.0089 (13)
N61D0.046 (2)0.0198 (17)0.024 (2)0.0018 (15)0.0129 (16)0.0069 (15)
N1E0.035 (2)0.0219 (18)0.0236 (19)0.0037 (14)0.0118 (15)0.0083 (15)
C2E0.024 (2)0.021 (2)0.018 (2)0.0021 (16)0.0070 (16)0.0049 (17)
N3E0.0319 (18)0.0168 (16)0.0244 (19)0.0039 (13)0.0046 (15)0.0087 (15)
C4E0.025 (2)0.020 (2)0.024 (2)0.0013 (16)0.0003 (17)0.0096 (18)
C5E0.042 (2)0.0151 (19)0.033 (3)0.0088 (17)0.007 (2)0.0088 (19)
C6E0.041 (2)0.020 (2)0.030 (2)0.0106 (18)0.006 (2)0.0052 (19)
O21E0.0461 (18)0.0204 (15)0.0303 (17)0.0059 (12)0.0131 (14)0.0119 (13)
N41E0.043 (2)0.0167 (17)0.030 (2)0.0037 (15)0.0092 (17)0.0110 (16)
F51E0.0746 (18)0.0188 (12)0.0492 (18)0.0163 (12)0.0251 (14)0.0143 (12)
N1F0.038 (2)0.0205 (17)0.0190 (19)0.0018 (14)0.0085 (15)0.0029 (15)
C2F0.028 (2)0.022 (2)0.018 (2)0.0001 (16)0.0041 (17)0.0037 (17)
N3F0.0274 (18)0.0210 (17)0.0181 (18)0.0014 (13)0.0046 (14)0.0041 (15)
C4F0.032 (2)0.023 (2)0.017 (2)0.0006 (17)0.0021 (17)0.0040 (18)
C5F0.040 (2)0.017 (2)0.027 (2)0.0010 (17)0.0033 (19)0.0056 (18)
C6F0.039 (2)0.027 (2)0.024 (2)0.0061 (18)0.0114 (19)0.0088 (19)
O21F0.0417 (17)0.0164 (14)0.0290 (17)0.0050 (12)0.0094 (13)0.0061 (12)
N41F0.046 (2)0.0194 (17)0.022 (2)0.0082 (15)0.0149 (16)0.0057 (16)
F51F0.0744 (18)0.0215 (12)0.0372 (16)0.0122 (12)0.0260 (13)0.0139 (12)
N1G0.0346 (19)0.0182 (16)0.0198 (18)0.0028 (14)0.0087 (15)0.0070 (15)
C2G0.027 (2)0.0138 (18)0.020 (2)0.0015 (15)0.0029 (17)0.0047 (17)
N3G0.0321 (19)0.0141 (17)0.024 (2)0.0023 (13)0.0091 (15)0.0068 (15)
C4G0.027 (2)0.023 (2)0.026 (2)0.0008 (16)0.0057 (17)0.0121 (18)
C5G0.033 (2)0.020 (2)0.024 (2)0.0037 (17)0.0160 (18)0.0070 (18)
C6G0.028 (2)0.022 (2)0.023 (2)0.0034 (16)0.0007 (17)0.0077 (18)
N21G0.040 (2)0.0117 (16)0.0214 (19)0.0037 (14)0.0116 (15)0.0055 (15)
O41G0.0398 (16)0.0171 (14)0.0337 (17)0.0052 (12)0.0138 (13)0.0122 (13)
N61G0.053 (2)0.0216 (18)0.028 (2)0.0057 (16)0.0173 (18)0.0042 (17)
N1H0.0348 (19)0.0156 (16)0.0190 (18)0.0004 (14)0.0077 (15)0.0068 (14)
C2H0.024 (2)0.0154 (19)0.017 (2)0.0026 (15)0.0023 (16)0.0015 (16)
N3H0.0270 (17)0.0166 (16)0.0189 (18)0.0033 (13)0.0045 (14)0.0063 (14)
C4H0.026 (2)0.0174 (19)0.027 (2)0.0021 (16)0.0008 (17)0.0079 (18)
C5H0.038 (2)0.0098 (18)0.028 (2)0.0028 (16)0.0058 (19)0.0037 (17)
C6H0.032 (2)0.0155 (19)0.020 (2)0.0018 (16)0.0058 (17)0.0006 (17)
O21H0.0391 (16)0.0155 (13)0.0270 (16)0.0002 (11)0.0099 (13)0.0092 (12)
N41H0.0366 (19)0.0152 (16)0.027 (2)0.0010 (14)0.0115 (15)0.0085 (15)
F51H0.0547 (15)0.0133 (11)0.0390 (15)0.0044 (10)0.0133 (12)0.0071 (11)
N1I0.0324 (19)0.0233 (18)0.0176 (18)0.0019 (14)0.0090 (15)0.0042 (15)
C2I0.027 (2)0.020 (2)0.019 (2)0.0024 (16)0.0026 (17)0.0070 (17)
N3I0.0297 (17)0.0139 (15)0.0159 (17)0.0030 (13)0.0020 (14)0.0024 (13)
C4I0.029 (2)0.021 (2)0.018 (2)0.0001 (16)0.0025 (17)0.0054 (17)
C5I0.032 (2)0.0182 (19)0.027 (2)0.0027 (16)0.0008 (18)0.0091 (18)
C6I0.029 (2)0.024 (2)0.020 (2)0.0008 (16)0.0055 (17)0.0115 (18)
O21I0.0397 (16)0.0162 (14)0.0291 (16)0.0038 (11)0.0134 (13)0.0063 (12)
N41I0.039 (2)0.0183 (16)0.026 (2)0.0000 (14)0.0075 (16)0.0040 (15)
F51I0.0510 (15)0.0141 (11)0.0365 (14)0.0005 (10)0.0033 (11)0.0103 (10)
O1Y0.0524 (19)0.0497 (19)0.0308 (18)0.0039 (15)0.0143 (15)0.0198 (16)
C2Y0.034 (2)0.033 (2)0.035 (3)0.0021 (19)0.002 (2)0.020 (2)
N3Y0.0326 (18)0.0295 (17)0.0202 (18)0.0048 (14)0.0056 (15)0.0109 (15)
C5Y0.044 (3)0.033 (2)0.041 (3)0.0074 (19)0.005 (2)0.021 (2)
C4Y0.048 (3)0.055 (3)0.034 (3)0.012 (2)0.010 (2)0.016 (2)
O1Z0.067 (2)0.0376 (18)0.0363 (19)0.0056 (15)0.0215 (16)0.0189 (16)
C2Z0.063 (3)0.028 (2)0.035 (3)0.011 (2)0.020 (2)0.008 (2)
N3Z0.042 (2)0.0276 (18)0.0223 (19)0.0067 (15)0.0115 (16)0.0088 (16)
C4Z0.053 (3)0.047 (3)0.033 (3)0.004 (2)0.001 (2)0.018 (2)
C5Z0.071 (4)0.033 (3)0.060 (4)0.015 (2)0.025 (3)0.009 (3)
Geometric parameters (Å, º) top
N1A—C2A1.328 (5)C4E—N41E1.347 (5)
N1A—C6A1.365 (5)C4E—C5E1.414 (6)
C2A—N21A1.340 (5)C5E—C6E1.354 (6)
C2A—N3A1.378 (5)C5E—F51E1.367 (4)
N3A—C4A1.395 (5)C6E—H6E0.9500
N3A—H3A0.87 (4)N41E—H41E0.889 (19)
C4A—O41A1.272 (4)N41E—H41F0.893 (19)
C4A—C5A1.391 (6)N1F—C6F1.357 (5)
C5A—C6A1.407 (5)N1F—C2F1.385 (5)
C5A—H5A0.9500N1F—H1F0.889 (19)
C6A—N61A1.347 (5)C2F—O21F1.260 (4)
N21A—H21A0.865 (19)C2F—N3F1.373 (5)
N21A—H21B0.880 (19)N3F—C4F1.338 (5)
N61A—H61A0.868 (19)C4F—N41F1.337 (5)
N61A—H61B0.890 (19)C4F—C5F1.423 (5)
N1B—C6B1.361 (5)C5F—C6F1.340 (6)
N1B—C2B1.376 (5)C5F—F51F1.364 (4)
N1B—H1B0.873 (19)C6F—H6F0.9500
C2B—O21B1.260 (4)N41F—H41G0.882 (19)
C2B—N3B1.378 (5)N41F—H41H0.877 (19)
N3B—C4B1.343 (5)N1G—C2G1.330 (5)
C4B—N41B1.323 (5)N1G—C6G1.368 (5)
C4B—C5B1.436 (6)C2G—N21G1.343 (5)
C5B—C6B1.329 (5)C2G—N3G1.371 (4)
C5B—F51B1.367 (4)N3G—C4G1.398 (5)
C6B—H6B0.9500N3G—H3G0.876 (19)
N41B—H41A0.892 (19)C4G—O41G1.266 (4)
N41B—H41B0.862 (19)C4G—C5G1.392 (5)
N1C—C6C1.355 (5)C5G—C6G1.412 (5)
N1C—C2C1.384 (5)C5G—H5G0.9500
N1C—H1C0.86 (5)C6G—N61G1.349 (5)
C2C—O21C1.256 (4)N21G—H21E0.91 (5)
C2C—N3C1.364 (5)N21G—H21F0.88 (4)
N3C—C4C1.354 (5)N61G—H61E0.85 (4)
C4C—N41C1.328 (5)N61G—H61F0.89 (5)
C4C—C5C1.429 (5)N1H—C6H1.355 (5)
C5C—C6C1.333 (6)N1H—C2H1.377 (5)
C5C—F51C1.358 (4)N1H—H1H0.870 (19)
C6C—H6C0.9500C2H—O21H1.268 (4)
N41C—H41C0.883 (19)C2H—N3H1.355 (4)
N41C—H41D0.893 (19)N3H—C4H1.364 (4)
O1X—C2X1.209 (5)C4H—N41H1.337 (5)
O1X—C2X'1.264 (9)C4H—C5H1.412 (6)
N3X—C2X'1.287 (9)C5H—C6H1.332 (5)
N3X—C2X1.374 (6)C5H—F51H1.382 (4)
N3X—C4X1.405 (6)C6H—H6H0.9500
N3X—C5X1.473 (6)N41H—H41I0.896 (19)
N3X—C4X'1.480 (9)N41H—H41J0.885 (19)
N3X—C5X'1.486 (9)N1I—C6I1.361 (5)
C2X—H2X10.9500N1I—C2I1.381 (5)
C4X—H4X10.9800N1I—H1I0.868 (19)
C4X—H4X20.9800C2I—O21I1.250 (4)
C4X—H4X30.9800C2I—N3I1.363 (5)
C5X—H5X10.9800N3I—C4I1.346 (4)
C5X—H5X20.9800C4I—N41I1.345 (5)
C5X—H5X30.9800C4I—C5I1.419 (5)
C2X'—H2X20.9500C5I—C6I1.325 (6)
C4X'—H4X40.9800C5I—F51I1.379 (4)
C4X'—H4X50.9800C6I—H6I0.9500
C4X'—H4X60.9800N41I—H41K0.880 (18)
C5X'—H5X40.9800N41I—H41L0.904 (19)
C5X'—H5X50.9800O1Y—C2Y1.211 (5)
C5X'—H5X60.9800C2Y—N3Y1.344 (4)
N1D—C2D1.344 (5)C2Y—H2Y0.9500
N1D—C6D1.375 (4)N3Y—C5Y1.456 (5)
C2D—N21D1.339 (5)N3Y—C4Y1.459 (6)
C2D—N3D1.360 (4)C5Y—H5Y10.9800
N3D—C4D1.392 (5)C5Y—H5Y20.9800
N3D—H3D0.903 (19)C5Y—H5Y30.9800
C4D—O41D1.277 (4)C4Y—H4Y10.9800
C4D—C5D1.403 (6)C4Y—H4Y20.9800
C5D—C6D1.392 (5)C4Y—H4Y30.9800
C5D—H5D0.9500O1Z—C2Z1.247 (5)
C6D—N61D1.362 (5)C2Z—N3Z1.321 (5)
N21D—H21C0.87 (5)C2Z—H2Z0.9500
N21D—H21D0.88 (4)N3Z—C5Z1.444 (6)
N61D—H61C0.897 (18)N3Z—C4Z1.450 (5)
N61D—H61D0.902 (19)C4Z—H4Z10.9800
N1E—C6E1.358 (5)C4Z—H4Z20.9800
N1E—C2E1.376 (5)C4Z—H4Z30.9800
N1E—H1E0.882 (19)C5Z—H5Z10.9800
C2E—O21E1.263 (4)C5Z—H5Z20.9800
C2E—N3E1.371 (5)C5Z—H5Z30.9800
N3E—C4E1.342 (5)
C2A—N1A—C6A117.2 (3)O21E—C2E—N3E121.3 (4)
N1A—C2A—N21A120.4 (3)O21E—C2E—N1E119.1 (3)
N1A—C2A—N3A122.6 (3)N3E—C2E—N1E119.6 (3)
N21A—C2A—N3A116.9 (4)C4E—N3E—C2E119.2 (4)
C2A—N3A—C4A121.6 (4)N3E—C4E—N41E118.8 (4)
C2A—N3A—H3A120 (3)N3E—C4E—C5E120.7 (3)
C4A—N3A—H3A119 (3)N41E—C4E—C5E120.5 (3)
O41A—C4A—C5A126.6 (3)C6E—C5E—F51E121.4 (4)
O41A—C4A—N3A117.0 (4)C6E—C5E—C4E120.1 (3)
C5A—C4A—N3A116.3 (3)F51E—C5E—C4E118.5 (3)
C4A—C5A—C6A119.2 (4)C5E—C6E—N1E118.2 (4)
C4A—C5A—H5A120.4C5E—C6E—H6E120.9
C6A—C5A—H5A120.4N1E—C6E—H6E120.9
N61A—C6A—N1A114.7 (3)C4E—N41E—H41E119 (3)
N61A—C6A—C5A122.4 (4)C4E—N41E—H41F120 (3)
N1A—C6A—C5A122.9 (4)H41E—N41E—H41F119 (4)
C2A—N21A—H21A117 (3)C6F—N1F—C2F121.5 (4)
C2A—N21A—H21B124 (3)C6F—N1F—H1F118 (3)
H21A—N21A—H21B119 (4)C2F—N1F—H1F121 (3)
C6A—N61A—H61A121 (3)O21F—C2F—N3F121.0 (3)
C6A—N61A—H61B125 (3)O21F—C2F—N1F119.4 (4)
H61A—N61A—H61B114 (4)N3F—C2F—N1F119.5 (3)
C6B—N1B—C2B122.2 (3)C4F—N3F—C2F119.7 (3)
C6B—N1B—H1B122 (3)N41F—C4F—N3F119.7 (3)
C2B—N1B—H1B116 (3)N41F—C4F—C5F120.4 (3)
O21B—C2B—N1B118.8 (3)N3F—C4F—C5F119.9 (4)
O21B—C2B—N3B121.8 (4)C6F—C5F—F51F120.8 (4)
N1B—C2B—N3B119.4 (3)C6F—C5F—C4F120.5 (3)
C4B—N3B—C2B119.5 (4)F51F—C5F—C4F118.7 (4)
N41B—C4B—N3B118.9 (4)C5F—C6F—N1F118.9 (4)
N41B—C4B—C5B121.6 (3)C5F—C6F—H6F120.6
N3B—C4B—C5B119.5 (3)N1F—C6F—H6F120.6
C6B—C5B—F51B122.6 (4)C4F—N41F—H41G125 (3)
C6B—C5B—C4B120.8 (3)C4F—N41F—H41H115 (3)
F51B—C5B—C4B116.6 (3)H41G—N41F—H41H118 (4)
C5B—C6B—N1B118.5 (4)C2G—N1G—C6G117.1 (3)
C5B—C6B—H6B120.7N1G—C2G—N21G120.0 (3)
N1B—C6B—H6B120.7N1G—C2G—N3G122.6 (3)
C4B—N41B—H41A124 (3)N21G—C2G—N3G117.4 (4)
C4B—N41B—H41B124 (3)C2G—N3G—C4G122.3 (3)
H41A—N41B—H41B112 (4)C2G—N3G—H3G118 (2)
C6C—N1C—C2C121.3 (4)C4G—N3G—H3G118 (3)
C6C—N1C—H1C116 (3)O41G—C4G—C5G127.3 (3)
C2C—N1C—H1C122 (3)O41G—C4G—N3G116.8 (4)
O21C—C2C—N3C121.1 (3)C5G—C4G—N3G115.8 (3)
O21C—C2C—N1C119.6 (4)C4G—C5G—C6G119.4 (3)
N3C—C2C—N1C119.3 (3)C4G—C5G—H5G120.3
C4C—N3C—C2C120.4 (3)C6G—C5G—H5G120.3
N41C—C4C—N3C119.6 (4)N61G—C6G—N1G114.6 (3)
N41C—C4C—C5C121.6 (3)N61G—C6G—C5G122.6 (4)
N3C—C4C—C5C118.9 (4)N1G—C6G—C5G122.8 (4)
C6C—C5C—F51C121.0 (4)C2G—N21G—H21E116 (2)
C6C—C5C—C4C120.3 (3)C2G—N21G—H21F115 (3)
F51C—C5C—C4C118.6 (4)H21E—N21G—H21F125 (4)
C5C—C6C—N1C119.7 (4)C6G—N61G—H61E122 (3)
C5C—C6C—H6C120.1C6G—N61G—H61F120 (3)
N1C—C6C—H6C120.1H61E—N61G—H61F118 (5)
C4C—N41C—H41C118 (3)C6H—N1H—C2H121.3 (3)
C4C—N41C—H41D115 (3)C6H—N1H—H1H120 (3)
H41C—N41C—H41D126 (4)C2H—N1H—H1H118 (3)
C2X—O1X—C2X'56.5 (6)O21H—C2H—N3H121.1 (3)
C2X'—N3X—C2X52.1 (7)O21H—C2H—N1H118.9 (3)
C2X'—N3X—C4X173.7 (10)N3H—C2H—N1H120.0 (3)
C2X—N3X—C4X122.5 (5)C2H—N3H—C4H119.4 (3)
C2X'—N3X—C5X65.5 (6)N41H—C4H—N3H118.0 (4)
C2X—N3X—C5X117.5 (4)N41H—C4H—C5H122.9 (3)
C4X—N3X—C5X119.9 (4)N3H—C4H—C5H119.1 (3)
C2X'—N3X—C4X'127.4 (11)C6H—C5H—F51H122.0 (4)
C2X—N3X—C4X'179.4 (11)C6H—C5H—C4H120.9 (3)
C4X—N3X—C4X'57.9 (9)F51H—C5H—C4H117.1 (3)
C5X—N3X—C4X'62.0 (9)C5H—C6H—N1H119.0 (4)
C2X'—N3X—C5X'124.7 (9)C5H—C6H—H6H120.5
C2X—N3X—C5X'72.6 (7)N1H—C6H—H6H120.5
C4X—N3X—C5X'50.2 (7)C4H—N41H—H41I121 (2)
C5X—N3X—C5X'168.6 (7)C4H—N41H—H41J116 (3)
C4X'—N3X—C5X'107.9 (10)H41I—N41H—H41J122 (4)
O1X—C2X—N3X124.2 (5)C6I—N1I—C2I121.1 (4)
O1X—C2X—H2X1117.9C6I—N1I—H1I113 (3)
N3X—C2X—H2X1117.9C2I—N1I—H1I126 (3)
N3X—C4X—H4X1109.5O21I—C2I—N3I121.0 (3)
N3X—C4X—H4X2109.5O21I—C2I—N1I119.7 (4)
H4X1—C4X—H4X2109.5N3I—C2I—N1I119.3 (3)
N3X—C4X—H4X3109.5C4I—N3I—C2I120.3 (3)
H4X1—C4X—H4X3109.5N3I—C4I—N41I118.6 (3)
H4X2—C4X—H4X3109.5N3I—C4I—C5I119.2 (4)
N3X—C5X—H5X1109.5N41I—C4I—C5I122.3 (3)
N3X—C5X—H5X2109.5C6I—C5I—F51I121.2 (3)
H5X1—C5X—H5X2109.5C6I—C5I—C4I120.7 (3)
N3X—C5X—H5X3109.5F51I—C5I—C4I118.0 (4)
H5X1—C5X—H5X3109.5C5I—C6I—N1I119.4 (3)
H5X2—C5X—H5X3109.5C5I—C6I—H6I120.3
O1X—C2X'—N3X127.1 (12)N1I—C6I—H6I120.3
O1X—C2X'—H2X2116.4C4I—N41I—H41K122 (3)
N3X—C2X'—H2X2116.4C4I—N41I—H41L119 (3)
N3X—C4X'—H4X4109.5H41K—N41I—H41L118 (4)
N3X—C4X'—H4X5109.5O1Y—C2Y—N3Y125.8 (4)
H4X4—C4X'—H4X5109.5O1Y—C2Y—H2Y117.1
N3X—C4X'—H4X6109.5N3Y—C2Y—H2Y117.1
H4X4—C4X'—H4X6109.5C2Y—N3Y—C5Y121.7 (4)
H4X5—C4X'—H4X6109.5C2Y—N3Y—C4Y120.5 (4)
N3X—C5X'—H5X4109.5C5Y—N3Y—C4Y117.8 (3)
N3X—C5X'—H5X5109.5N3Y—C5Y—H5Y1109.5
H5X4—C5X'—H5X5109.5N3Y—C5Y—H5Y2109.5
N3X—C5X'—H5X6109.5H5Y1—C5Y—H5Y2109.5
H5X4—C5X'—H5X6109.5N3Y—C5Y—H5Y3109.5
H5X5—C5X'—H5X6109.5H5Y1—C5Y—H5Y3109.5
C2D—N1D—C6D116.0 (3)H5Y2—C5Y—H5Y3109.5
N21D—C2D—N1D119.5 (3)N3Y—C4Y—H4Y1109.5
N21D—C2D—N3D118.1 (4)N3Y—C4Y—H4Y2109.5
N1D—C2D—N3D122.4 (3)H4Y1—C4Y—H4Y2109.5
C2D—N3D—C4D122.7 (4)N3Y—C4Y—H4Y3109.5
C2D—N3D—H3D115 (2)H4Y1—C4Y—H4Y3109.5
C4D—N3D—H3D121 (2)H4Y2—C4Y—H4Y3109.5
O41D—C4D—N3D116.9 (4)O1Z—C2Z—N3Z125.9 (5)
O41D—C4D—C5D126.7 (3)O1Z—C2Z—H2Z117.0
N3D—C4D—C5D116.3 (3)N3Z—C2Z—H2Z117.0
C6D—C5D—C4D118.1 (3)C2Z—N3Z—C5Z121.1 (4)
C6D—C5D—H5D120.9C2Z—N3Z—C4Z121.8 (4)
C4D—C5D—H5D120.9C5Z—N3Z—C4Z117.1 (3)
N61D—C6D—N1D114.6 (3)N3Z—C4Z—H4Z1109.5
N61D—C6D—C5D121.0 (3)N3Z—C4Z—H4Z2109.5
N1D—C6D—C5D124.3 (4)H4Z1—C4Z—H4Z2109.5
C2D—N21D—H21C119 (2)N3Z—C4Z—H4Z3109.5
C2D—N21D—H21D122 (3)H4Z1—C4Z—H4Z3109.5
H21C—N21D—H21D117 (4)H4Z2—C4Z—H4Z3109.5
C6D—N61D—H61C112 (3)N3Z—C5Z—H5Z1109.5
C6D—N61D—H61D120 (3)N3Z—C5Z—H5Z2109.5
H61C—N61D—H61D123 (4)H5Z1—C5Z—H5Z2109.5
C6E—N1E—C2E122.3 (3)N3Z—C5Z—H5Z3109.5
C6E—N1E—H1E121 (3)H5Z1—C5Z—H5Z3109.5
C2E—N1E—H1E116 (3)H5Z2—C5Z—H5Z3109.5
C6A—N1A—C2A—N21A179.2 (3)C2E—N3E—C4E—N41E179.5 (4)
C6A—N1A—C2A—N3A2.2 (5)C2E—N3E—C4E—C5E0.4 (6)
N1A—C2A—N3A—C4A2.9 (6)N3E—C4E—C5E—C6E0.8 (6)
N21A—C2A—N3A—C4A180.0 (4)N41E—C4E—C5E—C6E178.3 (4)
C2A—N3A—C4A—O41A178.7 (3)N3E—C4E—C5E—F51E178.8 (3)
C2A—N3A—C4A—C5A0.5 (6)N41E—C4E—C5E—F51E0.3 (6)
O41A—C4A—C5A—C6A175.7 (4)F51E—C5E—C6E—N1E178.9 (4)
N3A—C4A—C5A—C6A2.2 (6)C4E—C5E—C6E—N1E0.9 (6)
C2A—N1A—C6A—N61A177.2 (4)C2E—N1E—C6E—C5E0.1 (6)
C2A—N1A—C6A—C5A0.7 (6)C6F—N1F—C2F—O21F179.5 (4)
C4A—C5A—C6A—N61A174.8 (4)C6F—N1F—C2F—N3F0.2 (6)
C4A—C5A—C6A—N1A3.0 (6)O21F—C2F—N3F—C4F179.3 (4)
C6B—N1B—C2B—O21B178.5 (4)N1F—C2F—N3F—C4F1.0 (5)
C6B—N1B—C2B—N3B2.1 (6)C2F—N3F—C4F—N41F177.2 (4)
O21B—C2B—N3B—C4B178.3 (4)C2F—N3F—C4F—C5F2.0 (5)
N1B—C2B—N3B—C4B2.3 (5)N41F—C4F—C5F—C6F177.3 (4)
C2B—N3B—C4B—N41B179.8 (4)N3F—C4F—C5F—C6F1.9 (6)
C2B—N3B—C4B—C5B1.1 (5)N41F—C4F—C5F—F51F3.2 (6)
N41B—C4B—C5B—C6B178.7 (4)N3F—C4F—C5F—F51F177.6 (3)
N3B—C4B—C5B—C6B0.3 (6)F51F—C5F—C6F—N1F178.8 (4)
N41B—C4B—C5B—F51B1.0 (6)C4F—C5F—C6F—N1F0.7 (6)
N3B—C4B—C5B—F51B180.0 (3)C2F—N1F—C6F—C5F0.3 (6)
F51B—C5B—C6B—N1B179.7 (4)C6G—N1G—C2G—N21G179.6 (3)
C4B—C5B—C6B—N1B0.6 (6)C6G—N1G—C2G—N3G0.7 (5)
C2B—N1B—C6B—C5B0.6 (6)N1G—C2G—N3G—C4G0.2 (6)
C6C—N1C—C2C—O21C178.0 (4)N21G—C2G—N3G—C4G179.6 (3)
C6C—N1C—C2C—N3C1.4 (6)C2G—N3G—C4G—O41G178.4 (3)
O21C—C2C—N3C—C4C179.0 (4)C2G—N3G—C4G—C5G1.7 (5)
N1C—C2C—N3C—C4C0.4 (6)O41G—C4G—C5G—C6G177.7 (4)
C2C—N3C—C4C—N41C178.3 (4)N3G—C4G—C5G—C6G2.3 (6)
C2C—N3C—C4C—C5C1.7 (5)C2G—N1G—C6G—N61G177.7 (4)
N41C—C4C—C5C—C6C177.1 (4)C2G—N1G—C6G—C5G0.1 (5)
N3C—C4C—C5C—C6C2.9 (6)C4G—C5G—C6G—N61G176.0 (4)
N41C—C4C—C5C—F51C0.4 (6)C4G—C5G—C6G—N1G1.6 (6)
N3C—C4C—C5C—F51C179.6 (3)C6H—N1H—C2H—O21H175.6 (3)
F51C—C5C—C6C—N1C179.4 (4)C6H—N1H—C2H—N3H5.9 (5)
C4C—C5C—C6C—N1C1.9 (6)O21H—C2H—N3H—C4H176.3 (3)
C2C—N1C—C6C—C5C0.2 (6)N1H—C2H—N3H—C4H5.2 (5)
C2X'—O1X—C2X—N3X1.7 (17)C2H—N3H—C4H—N41H179.3 (3)
C2X'—N3X—C2X—O1X1.7 (17)C2H—N3H—C4H—C5H0.6 (5)
C4X—N3X—C2X—O1X177.6 (5)N41H—C4H—C5H—C6H174.9 (4)
C5X—N3X—C2X—O1X2.7 (7)N3H—C4H—C5H—C6H3.7 (6)
C5X'—N3X—C2X—O1X177.0 (10)N41H—C4H—C5H—F51H3.3 (6)
C2X—O1X—C2X'—N3X1.9 (19)N3H—C4H—C5H—F51H178.1 (3)
C2X—N3X—C2X'—O1X1.7 (17)F51H—C5H—C6H—N1H178.7 (3)
C5X—N3X—C2X'—O1X174 (3)C4H—C5H—C6H—N1H3.2 (6)
C4X'—N3X—C2X'—O1X179 (2)C2H—N1H—C6H—C5H1.5 (6)
C5X'—N3X—C2X'—O1X0 (4)C6I—N1I—C2I—O21I179.9 (3)
C6D—N1D—C2D—N21D178.4 (3)C6I—N1I—C2I—N3I1.7 (5)
C6D—N1D—C2D—N3D1.8 (5)O21I—C2I—N3I—C4I179.0 (3)
N21D—C2D—N3D—C4D179.8 (4)N1I—C2I—N3I—C4I0.7 (5)
N1D—C2D—N3D—C4D0.4 (6)C2I—N3I—C4I—N41I179.2 (3)
C2D—N3D—C4D—O41D178.7 (4)C2I—N3I—C4I—C5I1.3 (5)
C2D—N3D—C4D—C5D0.8 (5)N3I—C4I—C5I—C6I2.6 (6)
O41D—C4D—C5D—C6D176.8 (4)N41I—C4I—C5I—C6I178.0 (4)
N3D—C4D—C5D—C6D2.6 (5)N3I—C4I—C5I—F51I177.4 (3)
C2D—N1D—C6D—N61D177.0 (3)N41I—C4I—C5I—F51I2.1 (6)
C2D—N1D—C6D—C5D3.8 (5)F51I—C5I—C6I—N1I178.3 (3)
C4D—C5D—C6D—N61D176.6 (4)C4I—C5I—C6I—N1I1.6 (6)
C4D—C5D—C6D—N1D4.3 (6)C2I—N1I—C6I—C5I0.5 (6)
C6E—N1E—C2E—O21E178.9 (4)O1Y—C2Y—N3Y—C5Y1.3 (6)
C6E—N1E—C2E—N3E1.3 (6)O1Y—C2Y—N3Y—C4Y178.7 (4)
O21E—C2E—N3E—C4E178.7 (4)O1Z—C2Z—N3Z—C5Z2.4 (8)
N1E—C2E—N3E—C4E1.4 (5)O1Z—C2Z—N3Z—C4Z179.1 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3A—H3A···N3B0.87 (4)2.02 (5)2.894 (5)178 (4)
N21A—H21A···N1Ai0.87 (2)2.11 (2)2.977 (4)178 (4)
N21A—H21B···O21B0.88 (2)2.03 (2)2.909 (5)178 (4)
N61A—H61B···O1X0.89 (2)2.02 (2)2.884 (5)164 (4)
N1B—H1B···N3C0.87 (2)1.94 (2)2.815 (4)177 (4)
N41B—H41A···O41A0.89 (2)1.99 (2)2.878 (5)174 (4)
N41B—H41B···O41Aii0.86 (2)2.05 (3)2.860 (4)156 (4)
N1C—H1C···O21Ciii0.86 (5)1.92 (5)2.780 (5)178 (4)
N41C—H41D···O21B0.89 (2)2.13 (2)3.010 (4)167 (4)
N41C—H41C···O1Xi0.88 (2)2.25 (2)3.094 (4)160 (4)
N3D—H3D···N3E0.90 (2)2.00 (2)2.898 (5)177 (4)
N21D—H21D···N1Giv0.88 (4)2.13 (4)2.996 (4)173 (4)
N21D—H21C···O21E0.87 (5)2.05 (5)2.903 (5)167 (4)
N61D—H61D···O1Y0.90 (2)2.01 (2)2.885 (4)163 (4)
N1E—H1E···N3F0.88 (2)1.93 (2)2.801 (4)172 (4)
N41E—H41F···O41D0.89 (2)1.97 (2)2.861 (5)175 (4)
N41E—H41E···O41Gv0.89 (2)2.08 (3)2.895 (4)151 (4)
N1F—H1F···O21I0.89 (2)1.89 (2)2.768 (4)168 (4)
N41F—H41H···O21E0.88 (2)2.12 (2)2.999 (4)179 (4)
N41F—H41G···O1Ziv0.88 (2)2.23 (2)3.112 (4)173 (4)
N3G—H3G···N3H0.88 (2)2.03 (2)2.904 (5)174 (4)
N21G—H21F···N1Dvi0.88 (4)2.09 (4)2.968 (4)176 (4)
N21G—H21E···O21H0.91 (5)2.03 (5)2.933 (5)171 (3)
N61G—H61F···O1Z0.89 (5)2.05 (5)2.866 (5)153 (4)
N1H—H1H···N3I0.87 (2)1.94 (2)2.809 (4)176 (4)
N41H—H41I···O41G0.90 (2)1.97 (2)2.865 (5)173 (4)
N41H—H41J···O41Dvii0.89 (2)2.09 (3)2.847 (4)143 (4)
N1I—H1I···O21F0.87 (2)1.90 (2)2.762 (4)173 (4)
N41I—H41L···O21H0.90 (2)2.07 (2)2.974 (4)174 (4)
N41I—H41K···O21Hviii0.88 (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, z1; (v) x+1, y, z1; (vi) x1, y1, z+1; (vii) x1, y, z+1; (viii) x, y, z+2.
(VI) top
Crystal data top
C8H11N5O3Z = 4
Mr = 225.22F(000) = 472
Monoclinic, P21/cDx = 1.620 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.9182 (11) ÅCell parameters from 3262 reflections
b = 11.1666 (8) Åθ = 3.3–25.9°
c = 7.9786 (9) ŵ = 0.13 mm1
β = 108.346 (8)°T = 173 K
V = 923.30 (15) Å30.20 × 0.10 × 0.10 mm
Data collection top
STOE IPDS II two-circle-
diffractometer
1215 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.132
Graphite monochromatorθmax = 25.6°, θmin = 3.3°
ω scansh = 1313
6501 measured reflectionsk = 1313
1723 independent reflectionsl = 89
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0711P)2]
where P = (Fo2 + 2Fc2)/3
1723 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.27 e Å3
3 restraintsΔρmin = 0.32 e Å3
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.9389 (2)0.62257 (19)0.6574 (3)0.0176 (5)
H10.989 (3)0.565 (2)0.717 (4)0.021*
C20.8285 (3)0.5945 (2)0.5242 (4)0.0171 (5)
N30.7498 (2)0.6754 (2)0.4241 (3)0.0179 (5)
C40.7903 (3)0.7886 (2)0.4713 (4)0.0167 (6)
C50.8981 (2)0.8258 (2)0.6046 (4)0.0168 (5)
C60.9832 (3)0.7382 (2)0.7059 (4)0.0168 (6)
N70.9048 (2)0.95018 (19)0.6117 (3)0.0193 (5)
C80.8037 (3)0.9860 (2)0.4840 (4)0.0182 (6)
H80.78311.06790.45680.022*
N90.7299 (2)0.8920 (2)0.3929 (3)0.0180 (5)
N210.7989 (2)0.4779 (2)0.4990 (3)0.0228 (5)
H21A0.726 (2)0.460 (3)0.420 (4)0.027*
H21B0.851 (3)0.422 (3)0.561 (4)0.027*
O611.08727 (19)0.75473 (17)0.8263 (3)0.0237 (5)
C910.6116 (3)0.8976 (2)0.2434 (4)0.0178 (5)
H91A0.62420.95510.15570.021*
H91B0.59510.81790.18650.021*
O920.50241 (18)0.93261 (16)0.2897 (3)0.0193 (5)
C930.4725 (3)0.8573 (2)0.4169 (4)0.0206 (6)
H93A0.40840.89870.46090.025*
H93B0.55170.84570.51850.025*
C940.4195 (3)0.7356 (2)0.3464 (4)0.0200 (6)
H94A0.48520.69150.30920.024*
H94B0.40140.68920.44170.024*
O950.3043 (2)0.74536 (19)0.2006 (3)0.0268 (5)
H950.24050.75010.23770.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0152 (11)0.0138 (11)0.0216 (12)0.0001 (8)0.0027 (9)0.0005 (8)
C20.0160 (12)0.0167 (12)0.0202 (14)0.0017 (10)0.0080 (11)0.0019 (10)
N30.0189 (11)0.0152 (11)0.0190 (11)0.0006 (9)0.0053 (9)0.0011 (8)
C40.0170 (12)0.0173 (12)0.0172 (13)0.0011 (10)0.0075 (11)0.0025 (10)
C50.0153 (12)0.0142 (12)0.0203 (13)0.0038 (10)0.0046 (11)0.0019 (10)
C60.0160 (13)0.0156 (12)0.0183 (14)0.0001 (9)0.0047 (11)0.0007 (9)
N70.0193 (11)0.0130 (11)0.0244 (12)0.0021 (9)0.0051 (10)0.0007 (9)
C80.0184 (13)0.0116 (11)0.0248 (14)0.0006 (10)0.0069 (11)0.0014 (10)
N90.0194 (11)0.0142 (10)0.0198 (12)0.0015 (9)0.0055 (10)0.0016 (8)
N210.0237 (12)0.0136 (11)0.0256 (13)0.0004 (10)0.0002 (10)0.0006 (9)
O610.0197 (10)0.0190 (10)0.0274 (11)0.0020 (7)0.0000 (9)0.0002 (8)
C910.0185 (12)0.0181 (12)0.0164 (13)0.0019 (10)0.0048 (11)0.0026 (10)
O920.0176 (9)0.0156 (9)0.0234 (11)0.0018 (7)0.0047 (8)0.0021 (7)
C930.0210 (13)0.0230 (14)0.0185 (14)0.0003 (11)0.0071 (11)0.0009 (10)
C940.0198 (13)0.0193 (13)0.0200 (14)0.0024 (10)0.0049 (11)0.0006 (10)
O950.0209 (10)0.0308 (11)0.0236 (11)0.0053 (9)0.0002 (9)0.0004 (8)
Geometric parameters (Å, º) top
N1—C21.369 (4)N9—C911.458 (3)
N1—C61.390 (3)N21—H21A0.864 (19)
N1—H10.885 (18)N21—H21B0.881 (19)
C2—N31.327 (4)C91—O921.410 (3)
C2—N211.342 (4)C91—H91A0.9900
N3—C41.353 (4)C91—H91B0.9900
C4—N91.378 (3)O92—C931.433 (3)
C4—C51.379 (4)C93—C941.513 (4)
C5—N71.391 (4)C93—H93A0.9900
C5—C61.414 (4)C93—H93B0.9900
C6—O611.250 (3)C94—O951.423 (3)
N7—C81.307 (4)C94—H94A0.9900
C8—N91.383 (4)C94—H94B0.9900
C8—H80.9500O95—H950.8400
C2—N1—C6124.9 (2)C2—N21—H21A117 (2)
C2—N1—H1120 (2)C2—N21—H21B121 (2)
C6—N1—H1115 (2)H21A—N21—H21B122 (3)
N3—C2—N21119.4 (3)O92—C91—N9113.7 (2)
N3—C2—N1123.8 (2)O92—C91—H91A108.8
N21—C2—N1116.8 (2)N9—C91—H91A108.8
C2—N3—C4112.0 (2)O92—C91—H91B108.8
N3—C4—N9126.0 (2)N9—C91—H91B108.8
N3—C4—C5128.4 (2)H91A—C91—H91B107.7
N9—C4—C5105.6 (2)C91—O92—C93115.0 (2)
C4—C5—N7110.7 (2)O92—C93—C94114.2 (2)
C4—C5—C6118.7 (2)O92—C93—H93A108.7
N7—C5—C6130.6 (3)C94—C93—H93A108.7
O61—C6—N1120.2 (2)O92—C93—H93B108.7
O61—C6—C5127.7 (2)C94—C93—H93B108.7
N1—C6—C5112.0 (2)H93A—C93—H93B107.6
C8—N7—C5104.7 (2)O95—C94—C93111.8 (2)
N7—C8—N9112.8 (2)O95—C94—H94A109.3
N7—C8—H8123.6C93—C94—H94A109.3
N9—C8—H8123.6O95—C94—H94B109.3
C4—N9—C8106.3 (2)C93—C94—H94B109.3
C4—N9—C91125.6 (2)H94A—C94—H94B107.9
C8—N9—C91128.1 (2)C94—O95—H95109.5
C6—N1—C2—N30.2 (4)N7—C5—C6—N1179.0 (3)
C6—N1—C2—N21178.3 (2)C4—C5—N7—C80.6 (3)
N21—C2—N3—C4177.3 (2)C6—C5—N7—C8177.6 (3)
N1—C2—N3—C41.2 (4)C5—N7—C8—N90.2 (3)
C2—N3—C4—N9179.9 (2)N3—C4—N9—C8179.5 (2)
C2—N3—C4—C50.1 (4)C5—C4—N9—C80.5 (3)
N3—C4—C5—N7179.3 (2)N3—C4—N9—C910.6 (4)
N9—C4—C5—N70.7 (3)C5—C4—N9—C91179.4 (2)
N3—C4—C5—C62.3 (4)N7—C8—N9—C40.2 (3)
N9—C4—C5—C6177.7 (2)N7—C8—N9—C91179.7 (2)
C2—N1—C6—O61178.0 (3)C4—N9—C91—O92105.8 (3)
C2—N1—C6—C51.9 (4)C8—N9—C91—O9274.3 (3)
C4—C5—C6—O61177.0 (3)N9—C91—O92—C9358.4 (3)
N7—C5—C6—O611.1 (5)C91—O92—C93—C9471.4 (3)
C4—C5—C6—N12.9 (4)O92—C93—C94—O9559.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N7i0.89 (2)1.96 (2)2.834 (3)169 (3)
N21—H21A···O95ii0.86 (2)2.56 (3)3.069 (3)118 (3)
N21—H21B···O61i0.88 (2)2.09 (2)2.934 (3)159 (3)
O95—H95···O61iii0.842.012.849 (3)175
Symmetry codes: (i) x+2, y1/2, z+3/2; (ii) x+1, y1/2, z+1/2; (iii) x1, y+3/2, z1/2.
(VII) ; top
Crystal data top
C4H4FN3O·C8H11N5O3F(000) = 736
Mr = 354.32Dx = 1.622 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9824 reflections
a = 7.0859 (5) Åθ = 3.6–26.0°
b = 9.0414 (5) ŵ = 0.13 mm1
c = 22.8754 (16) ÅT = 173 K
β = 98.155 (6)°Block, colourless
V = 1450.73 (16) Å30.60 × 0.60 × 0.40 mm
Z = 4
Data collection top
STOE IPDS II two-circle-
diffractometer
2202 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.073
Graphite monochromatorθmax = 25.7°, θmin = 3.5°
ω scansh = 88
11519 measured reflectionsk = 1110
2718 independent reflectionsl = 2327
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0688P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
2718 reflectionsΔρmax = 0.34 e Å3
252 parametersΔρmin = 0.33 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.020 (3)
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.31615 (16)0.63847 (13)0.46492 (6)0.0191 (3)
H10.282 (2)0.5820 (19)0.4938 (8)0.028 (5)*
C20.38770 (19)0.77873 (16)0.47575 (6)0.0193 (3)
N210.4025 (2)0.82458 (17)0.53167 (6)0.0271 (3)
H21A0.375 (3)0.764 (2)0.5596 (9)0.033 (5)*
H21B0.447 (3)0.913 (2)0.5402 (10)0.039 (5)*
N30.43674 (16)0.86735 (13)0.43384 (5)0.0192 (3)
C40.40557 (18)0.80386 (16)0.37951 (6)0.0178 (3)
C50.33311 (19)0.66518 (16)0.36467 (6)0.0186 (3)
C60.28091 (19)0.57301 (15)0.40952 (7)0.0189 (3)
O610.20669 (15)0.44856 (11)0.40312 (5)0.0262 (3)
N70.31657 (17)0.64076 (14)0.30431 (5)0.0223 (3)
C80.3794 (2)0.76291 (16)0.28366 (7)0.0216 (3)
H80.38510.77900.24290.026*
N90.43674 (16)0.86634 (13)0.32676 (5)0.0185 (3)
C910.49976 (19)1.01439 (16)0.31408 (7)0.0204 (3)
H91A0.56351.06050.35090.025*
H91B0.59341.00850.28590.025*
O920.34457 (14)1.10231 (11)0.28994 (4)0.0217 (3)
C930.2348 (2)1.15385 (18)0.33420 (7)0.0275 (4)
H93A0.31091.22500.36070.033*
H93B0.20101.06950.35830.033*
C940.0568 (2)1.22747 (19)0.30455 (8)0.0319 (4)
H94A0.01621.15560.27760.038*
H94B0.02321.25510.33500.038*
O950.09130 (19)1.35572 (13)0.27195 (6)0.0375 (3)
H950.15211.41780.29460.045*
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)
H41A0.138 (3)0.319 (2)0.4610 (9)0.050 (6)*
H41B0.068 (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)
H6'0.11610.20730.68120.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0229 (6)0.0170 (6)0.0182 (6)0.0025 (5)0.0052 (5)0.0004 (5)
C20.0197 (6)0.0177 (7)0.0207 (8)0.0008 (5)0.0033 (5)0.0028 (6)
N210.0425 (8)0.0232 (7)0.0165 (7)0.0116 (6)0.0072 (6)0.0029 (6)
N30.0237 (6)0.0170 (6)0.0171 (6)0.0015 (5)0.0030 (5)0.0009 (5)
C40.0163 (6)0.0188 (7)0.0185 (7)0.0026 (5)0.0034 (5)0.0001 (6)
C50.0190 (6)0.0174 (7)0.0195 (8)0.0020 (5)0.0026 (5)0.0023 (6)
C60.0186 (6)0.0160 (7)0.0220 (7)0.0020 (5)0.0023 (5)0.0028 (6)
O610.0361 (6)0.0173 (6)0.0258 (6)0.0060 (4)0.0066 (4)0.0036 (4)
N70.0277 (6)0.0205 (7)0.0189 (7)0.0022 (5)0.0037 (5)0.0026 (5)
C80.0272 (7)0.0221 (8)0.0157 (7)0.0046 (6)0.0042 (6)0.0015 (6)
N90.0227 (6)0.0168 (6)0.0167 (6)0.0016 (5)0.0050 (5)0.0008 (5)
C910.0217 (7)0.0193 (7)0.0211 (7)0.0004 (5)0.0059 (5)0.0034 (6)
O920.0275 (5)0.0205 (6)0.0178 (5)0.0051 (4)0.0051 (4)0.0010 (4)
C930.0326 (8)0.0306 (9)0.0201 (8)0.0088 (7)0.0072 (6)0.0048 (7)
C940.0302 (8)0.0326 (9)0.0319 (9)0.0067 (7)0.0016 (7)0.0087 (7)
O950.0519 (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) top
N1—C21.3751 (19)C93—C941.500 (2)
N1—C61.3888 (19)C93—H93A0.9900
N1—H10.895 (15)C93—H93B0.9900
C2—N31.3328 (19)C94—O951.419 (2)
C2—N211.335 (2)C94—H94A0.9900
N21—H21A0.88 (2)C94—H94B0.9900
N21—H21B0.87 (2)O95—H950.8400
N3—C41.3583 (19)N1'—C6'1.360 (2)
C4—N91.3783 (19)N1'—C2'1.384 (2)
C4—C51.379 (2)N1'—H1'0.88 (2)
C5—N71.3866 (19)C2'—O21'1.240 (2)
C5—C61.411 (2)C2'—N3'1.361 (2)
C6—O611.2418 (18)N3'—C4'1.336 (2)
N7—C81.304 (2)C4'—N41'1.330 (2)
C8—N91.3775 (19)C4'—C5'1.423 (2)
C8—H80.9500N41'—H41A0.908 (16)
N9—C911.4533 (19)N41'—H41B0.90 (2)
C91—O921.4049 (17)C5'—C6'1.332 (2)
C91—H91A0.9900C5'—F51'1.3643 (19)
C91—H91B0.9900C6'—H6'0.9500
O92—C931.4393 (18)
C2—N1—C6124.85 (13)O92—C93—C94109.22 (13)
C2—N1—H1121.7 (12)O92—C93—H93A109.8
C6—N1—H1113.4 (12)C94—C93—H93A109.8
N3—C2—N21120.64 (14)O92—C93—H93B109.8
N3—C2—N1123.50 (13)C94—C93—H93B109.8
N21—C2—N1115.85 (14)H93A—C93—H93B108.3
C2—N21—H21A120.5 (13)O95—C94—C93113.83 (14)
C2—N21—H21B118.4 (14)O95—C94—H94A108.8
H21A—N21—H21B121.0 (19)C93—C94—H94A108.8
C2—N3—C4112.26 (12)O95—C94—H94B108.8
N3—C4—N9127.04 (13)C93—C94—H94B108.8
N3—C4—C5128.03 (14)H94A—C94—H94B107.7
N9—C4—C5104.91 (13)C94—O95—H95109.5
C4—C5—N7111.46 (13)C6'—N1'—C2'122.69 (15)
C4—C5—C6118.99 (13)C6'—N1'—H1'116.3 (14)
N7—C5—C6129.50 (13)C2'—N1'—H1'121.0 (14)
O61—C6—N1120.80 (14)O21'—C2'—N3'122.22 (14)
O61—C6—C5126.83 (14)O21'—C2'—N1'119.44 (15)
N1—C6—C5112.33 (12)N3'—C2'—N1'118.34 (14)
C8—N7—C5103.93 (12)C4'—N3'—C2'120.48 (14)
N7—C8—N9113.38 (13)N41'—C4'—N3'119.83 (15)
N7—C8—H8123.3N41'—C4'—C5'120.39 (15)
N9—C8—H8123.3N3'—C4'—C5'119.78 (15)
C8—N9—C4106.31 (12)C4'—N41'—H41A119.3 (15)
C8—N9—C91123.38 (12)C4'—N41'—H41B122.7 (15)
C4—N9—C91130.10 (12)H41A—N41'—H41B118 (2)
O92—C91—N9110.74 (11)C6'—C5'—F51'121.44 (15)
O92—C91—H91A109.5C6'—C5'—C4'120.64 (15)
N9—C91—H91A109.5F51'—C5'—C4'117.92 (15)
O92—C91—H91B109.5C5'—C6'—N1'118.05 (15)
N9—C91—H91B109.5C5'—C6'—H6'121.0
H91A—C91—H91B108.1N1'—C6'—H6'121.0
C91—O92—C93112.19 (11)
C6—N1—C2—N31.9 (2)C5—C4—N9—C80.70 (14)
C6—N1—C2—N21176.72 (13)N3—C4—N9—C913.5 (2)
N21—C2—N3—C4177.76 (13)C5—C4—N9—C91175.42 (13)
N1—C2—N3—C40.79 (19)C8—N9—C91—O9273.11 (16)
C2—N3—C4—N9178.48 (13)C4—N9—C91—O92100.82 (16)
C2—N3—C4—C50.2 (2)N9—C91—O92—C9377.46 (15)
N3—C4—C5—N7178.21 (12)C91—O92—C93—C94171.75 (13)
N9—C4—C5—N70.67 (15)O92—C93—C94—O9563.25 (18)
N3—C4—C5—C60.5 (2)C6'—N1'—C2'—O21'179.03 (13)
N9—C4—C5—C6178.37 (12)C6'—N1'—C2'—N3'0.5 (2)
C2—N1—C6—O61176.19 (13)O21'—C2'—N3'—C4'179.74 (13)
C2—N1—C6—C52.03 (19)N1'—C2'—N3'—C4'0.2 (2)
C4—C5—C6—O61176.76 (13)C2'—N3'—C4'—N41'178.75 (13)
N7—C5—C6—O610.5 (2)C2'—N3'—C4'—C5'1.0 (2)
C4—C5—C6—N11.33 (18)N41'—C4'—C5'—C6'178.61 (14)
N7—C5—C6—N1178.55 (13)N3'—C4'—C5'—C6'1.2 (2)
C4—C5—N7—C80.36 (15)N41'—C4'—C5'—F51'1.3 (2)
C6—C5—N7—C8177.75 (14)N3'—C4'—C5'—F51'178.90 (12)
C5—N7—C8—N90.11 (15)F51'—C5'—C6'—N1'179.60 (12)
N7—C8—N9—C40.53 (16)C4'—C5'—C6'—N1'0.5 (2)
N7—C8—N9—C91175.70 (12)C2'—N1'—C6'—C5'0.4 (2)
N3—C4—N9—C8178.21 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N30.90 (2)2.00 (2)2.8964 (18)176 (2)
N21—H21B···N3i0.87 (2)2.20 (2)3.0698 (19)177 (2)
N21—H21A···O210.88 (2)2.05 (2)2.9317 (19)179.7 (19)
O95—H95···N7ii0.842.323.0663 (18)148
O95—H95···O61ii0.842.473.1112 (16)134
N1—H1···O92iii0.88 (2)2.22 (2)3.0246 (18)151.6 (19)
N41—H41A···O610.91 (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.
 

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