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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Amicarbazone

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and dDepartment of Chemistry, G. Madegowda Institute of Technology, Bharathinagara 571 422, India
*Correspondence e-mail: jjasinski@keene.edu

(Received 4 March 2013; accepted 20 March 2013; online 28 March 2013)

Three independent mol­ecules comprise the asymmetric unit of the title compound, C10H19N5O2, (systematic name: 4-amino-N-tert-butyl-3-isopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazole-1-carboxamide) . In all three mol­ecules, the triazole ring and the carboxamide group are almost coplanar [within 4.0–5.9 (9)°], particularly because of the formation of an intra­molecular N—H⋯O hydrogen bond. On other hand, the orientation of the isopropyl group varies significantly from mol­ecule to mol­ecule. The crystal packing is dominated by N—H⋯O and N—H⋯N hydrogen bonds, which connect the mol­ecules into infinite chains along [010].

Related literature

For herbicidal properties of amicarbazone and for its preparation, see: Dayan et al. (2009[Dayan, F. E., Trindade, M. L. B. & Velini, E. D. (2009). Weed Sci. 57, 579-583.]); Diehr (1998[Diehr (1998). US Patent No. US005708184A.]). For related structures, see: Crockett et al. (2004[Crockett, R., Forrester, A. R. & Howie, R. A. (2004). Acta Cryst. E60, o460-o461.]); Dupont et al. (1991[Dupont, L., Englebert, S., Dideberg, O., Pirotte, B. & Delarge, J. (1991). Acta Cryst. C47, 1557-1559.]); Heng et al. (2006[Heng, J., Zhu, H.-J., Tang, Q.-G. & Yan, H.-L. (2006). Acta Cryst. E62, o3111-o3112.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C10H19N5O2

  • Mr = 241.30

  • Triclinic, [P \overline 1]

  • a = 11.0298 (2) Å

  • b = 12.2135 (4) Å

  • c = 14.8542 (4) Å

  • α = 92.244 (2)°

  • β = 95.7020 (19)°

  • γ = 93.379 (2)°

  • V = 1985.65 (9) Å3

  • Z = 6

  • Cu Kα radiation

  • μ = 0.72 mm−1

  • T = 123 K

  • 0.35 × 0.25 × 0.15 mm

Data collection
  • Agilent Xcalibur (Ruby, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.791, Tmax = 1.000

  • 13380 measured reflections

  • 7959 independent reflections

  • 7592 reflections with I > 2σ(I)

  • Rint = 0.019

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.115

  • S = 1.05

  • 7959 reflections

  • 499 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N2A—H3N1⋯O1C 0.904 (19) 2.220 (19) 3.0832 (14) 159.6 (15)
N2A—H3N2⋯N3B 0.91 (2) 2.40 (2) 3.2251 (15) 150.9 (15)
N2A—H3N2⋯O2B 0.91 (2) 2.483 (19) 3.2492 (14) 141.7 (15)
N5A—H4AB⋯O1A 0.88 2.05 2.7770 (14) 140
N2B—H3B2⋯N3Ci 0.929 (19) 2.233 (19) 3.1619 (15) 179.1 (15)
N2B—H3B1⋯O1Bii 0.89 (2) 2.27 (2) 3.1356 (15) 163.1 (16)
N5B—H4BB⋯O1B 0.88 2.04 2.7655 (14) 139
N2C—H3C2⋯O1A 0.906 (18) 2.171 (18) 2.9455 (15) 143.1 (15)
N2C—H3C1⋯O2B 0.88 (2) 2.41 (2) 3.0718 (14) 132.8 (16)
N5C—H4CB⋯O1C 0.88 2.05 2.7721 (13) 139
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Amicarbazone (IUPAC name: 4-Amino-N-(tert-butyl)-4,5-dihydro-3- (iso-propyl)-5-oxo-1H-1,2,4-triazole-1-carboxamide) is a new triazolinone herbicide with a broad spectrum of weed control. The phenotypic responses of sensitive plants exposed to amicarbazone include chlorosis, stunted growth, tissue necrosis, and death. Its efficacy as both a foliar- and root-applied herbicide suggests that absorption and translocation of this compound is very rapid. This new herbicide is a potent inhibitor of photosynthetic electron transport, inducing chlorophyll fluorescence and interrupting oxygen evolution ostensibly via binding to the Qb domain of photosystem II (PSII) in a manner similar to the triazines and the triazinones classes of herbicides (Dayan et al., 2009). In view of the importance of amicarbazone derivatives, this paper reports the crystal and molecular structure of the title compound, (I), C10H19N5O2.

In (I), three independent molecules (A,B,C) crystallize in the asymmetric unit (Fig. 1). The dihedral angle between the mean planes of the triazole ring and carboxamide group (N4/C6/O2/N5) for each of the molecules lie between 4.0 (6)° and 5.9 (9)°. In each of the three molecules the torsion angles of the tert-butyl groups are quite similar [C6/N5/C7/C8 = -56.76 (17)° (A), 64.18 (17)° (B), -57.90 (17)° (C); C6/N5/C7/C9 = 66.03 (16)° (A), -57.99 (19)° (B), 64.87 (16)° (C); C6/N5/C7/C10 = -175.58 (12)° (A), -177.48 (19)° (B), -177.61 (13)° (C)] while those of the isopropyl group vary significantly [N3/C2/C3/C4 = 111.38(14° (A), 120.86 (14)° (B), 8.92 (17)° (C); N3/C2/C3/C5 = -11.65 (17)° (A), -113.15 (14)° (B), 88.83 (15)° (C)]. In the crystal molecular packing is dominated by N—H···O and N—H···N intermolecular interactions (Table 1) forming a network of infinite 1-D chains along [010] (Fig. 2).

Related literature top

For herbicidal properties of amicarbazone and for its preparation, see: Dayan et al. (2009); Diehr (1998). For related structures, see: Crockett et al. (2004); Dupont et al. (1991); Heng et al. (2006). For standard bond lengths, see: Allen et al. (1987).

Experimental top

Amicarbazone was prepared according to the patent procedure (Diehr, 1998). The resulting compound was recrystallized from methyl t-butyl ether by slow evaporation (M.P.: 373–378 K).

Refinement top

The amine H-atoms (H3N1, H3N2, H3B1, H3B2, H3C1, H3C2) were located by a difference map and refined isotropically. All of the remaining H atoms including the amide H atoms, were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 1.00Å (CH), 0.98Å (CH3) or 0.88Å (NH). Isotropic displacement parameters for these atoms were set to 1.18-1.20 (CH, NH) or 1.48-1.50 (CH3) times Ueq of the parent atom. All of the methyl groups were refined in idealized positions with their rotation angle optimized (AFIX 137).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the three independent molecules in the title compound showing the atom labeling scheme and 30% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound viewed along the c axis. Dashed lines indicate N—H···O intramolecular hydrogen bonds and weak N—H···O, N—H···N intermolecular interactions which form a network of infininte 1-D chains along [010]. H atoms not involved in hydrogen bonds or weak intermolecular interactions have been removed for clarity.
4-Amino-N-tert-butyl-5-oxo-3-(propan-2-yl)-1H-1,2,4-triazole-1-carboxamide top
Crystal data top
C10H19N5O2Z = 6
Mr = 241.30F(000) = 780
Triclinic, P1Dx = 1.211 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54184 Å
a = 11.0298 (2) ÅCell parameters from 11341 reflections
b = 12.2135 (4) Åθ = 3.0–75.4°
c = 14.8542 (4) ŵ = 0.72 mm1
α = 92.244 (2)°T = 123 K
β = 95.7020 (19)°Prism, colorless
γ = 93.379 (2)°0.35 × 0.25 × 0.15 mm
V = 1985.65 (9) Å3
Data collection top
Agilent Xcalibur (Ruby, Gemini)
diffractometer
7959 independent reflections
Radiation source: Enhance (Cu) X-ray Source7592 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 10.5081 pixels mm-1θmax = 75.6°, θmin = 3.0°
ω scansh = 139
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
k = 1315
Tmin = 0.791, Tmax = 1.000l = 1718
13380 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0642P)2 + 0.6558P]
where P = (Fo2 + 2Fc2)/3
7959 reflections(Δ/σ)max < 0.001
499 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C10H19N5O2γ = 93.379 (2)°
Mr = 241.30V = 1985.65 (9) Å3
Triclinic, P1Z = 6
a = 11.0298 (2) ÅCu Kα radiation
b = 12.2135 (4) ŵ = 0.72 mm1
c = 14.8542 (4) ÅT = 123 K
α = 92.244 (2)°0.35 × 0.25 × 0.15 mm
β = 95.7020 (19)°
Data collection top
Agilent Xcalibur (Ruby, Gemini)
diffractometer
7959 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
7592 reflections with I > 2σ(I)
Tmin = 0.791, Tmax = 1.000Rint = 0.019
13380 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.33 e Å3
7959 reflectionsΔρmin = 0.28 e Å3
499 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1A0.51333 (8)0.54857 (7)0.27512 (6)0.02404 (19)
O2A0.79068 (9)0.61028 (9)0.49492 (7)0.0338 (2)
N1A0.40274 (9)0.61234 (8)0.39102 (7)0.0195 (2)
N2A0.28358 (9)0.60744 (9)0.34749 (8)0.0228 (2)
H3N10.2623 (16)0.5362 (16)0.3316 (12)0.032 (4)*
H3N20.2814 (17)0.6526 (16)0.2999 (13)0.035 (4)*
N3A0.55089 (9)0.64321 (9)0.50255 (7)0.0223 (2)
N4A0.59586 (9)0.60225 (8)0.42386 (7)0.0212 (2)
N5A0.75776 (9)0.56285 (9)0.34326 (8)0.0242 (2)
H4AB0.69950.55130.29830.029*
C1A0.50547 (10)0.58304 (9)0.35331 (8)0.0196 (2)
C2A0.43486 (11)0.64838 (9)0.47960 (8)0.0201 (2)
C3A0.34541 (11)0.69354 (10)0.53838 (9)0.0237 (3)
H4AA0.27380.63910.53710.028*
C4A0.30062 (13)0.80053 (12)0.50000 (10)0.0315 (3)
H5AA0.25990.78540.43870.047*
H5AB0.37040.85350.49790.047*
H5AC0.24290.83090.53890.047*
C5A0.40205 (14)0.71189 (12)0.63627 (9)0.0305 (3)
H6AA0.42950.64230.65900.046*
H6AB0.34110.73930.67370.046*
H6AC0.47190.76580.63890.046*
C6A0.72576 (11)0.59224 (10)0.42504 (9)0.0233 (2)
C7A0.88576 (11)0.54861 (11)0.32375 (10)0.0271 (3)
C8A0.96498 (13)0.65373 (13)0.34987 (12)0.0372 (3)
H9AA0.96900.66850.41550.056*
H9AB0.92940.71510.31840.056*
H9AC1.04740.64510.33250.056*
C9A0.93520 (13)0.45147 (13)0.37431 (11)0.0363 (3)
H10A0.92830.46310.43920.054*
H10B1.02110.44520.36440.054*
H10C0.88790.38380.35170.054*
C10A0.87979 (14)0.52432 (15)0.22191 (11)0.0389 (3)
H11A0.84530.58570.18980.058*
H11B0.82810.45710.20550.058*
H11C0.96220.51450.20490.058*
O1B0.32055 (8)0.95985 (7)0.03184 (6)0.02541 (19)
O2B0.15234 (8)0.69360 (7)0.16012 (6)0.0269 (2)
N1B0.46600 (9)0.93184 (8)0.15285 (7)0.0201 (2)
N2B0.54880 (10)1.02214 (9)0.14557 (8)0.0242 (2)
H3B20.5068 (16)1.0854 (15)0.1505 (12)0.030 (4)*
H3B10.5749 (17)1.0154 (15)0.0910 (13)0.034 (4)*
N3B0.37300 (9)0.79451 (8)0.21715 (7)0.0221 (2)
N4B0.30260 (9)0.82468 (8)0.13967 (7)0.0211 (2)
N5B0.12373 (10)0.81232 (9)0.04498 (7)0.0258 (2)
H4BB0.16200.86340.01620.031*
C1B0.35739 (11)0.91208 (10)0.09966 (8)0.0206 (2)
C2B0.46927 (11)0.86178 (10)0.22317 (8)0.0208 (2)
C3B0.56869 (12)0.86298 (10)0.29937 (9)0.0261 (3)
H4BA0.54760.80160.33880.031*
C4B0.69240 (13)0.84177 (13)0.26659 (12)0.0381 (3)
H5BA0.68670.77110.23230.057*
H5BB0.75380.84010.31890.057*
H5BC0.71610.90050.22750.057*
C5B0.57330 (15)0.96978 (12)0.35741 (10)0.0354 (3)
H6BA0.49190.98140.37570.053*
H6BB0.59991.03140.32220.053*
H6BC0.63110.96490.41140.053*
C6B0.18508 (11)0.77003 (10)0.11635 (8)0.0214 (2)
C7B0.00412 (14)0.77871 (12)0.01138 (11)0.0363 (3)
C8B0.08729 (15)0.80880 (16)0.08385 (15)0.0514 (5)
H9BA0.07890.88830.09720.077*
H9BB0.06400.77050.13910.077*
H9BC0.17230.78690.06170.077*
C9B0.0174 (2)0.65528 (15)0.01308 (14)0.0556 (5)
H10D0.03740.63780.05890.083*
H10E0.10190.63450.03720.083*
H10F0.00380.61450.04120.083*
C10B0.0332 (2)0.84417 (17)0.07255 (14)0.0600 (6)
H11D0.01750.82160.11970.090*
H11E0.01620.92270.05700.090*
H11F0.11960.83030.09480.090*
O1C0.18247 (8)0.38918 (7)0.24910 (6)0.02389 (19)
O2C0.32253 (9)0.07163 (7)0.25786 (7)0.0297 (2)
N1C0.33153 (9)0.40112 (8)0.14853 (7)0.0196 (2)
N2C0.32178 (11)0.51004 (9)0.12243 (8)0.0232 (2)
H3C20.3638 (16)0.5511 (15)0.1687 (12)0.030 (4)*
H3C10.2454 (19)0.5268 (16)0.1224 (13)0.039 (5)*
N3C0.40591 (9)0.23804 (9)0.16020 (7)0.0222 (2)
N4C0.31110 (9)0.24896 (8)0.21498 (7)0.0200 (2)
N5C0.17403 (10)0.17616 (8)0.30715 (7)0.0227 (2)
H4CB0.14160.23980.30020.027*
C1C0.26465 (11)0.35096 (10)0.21013 (8)0.0192 (2)
C2C0.41530 (11)0.33083 (10)0.12170 (8)0.0201 (2)
C3C0.50113 (12)0.35820 (10)0.05267 (8)0.0234 (2)
H4CA0.51880.43960.05560.028*
C4C0.62141 (13)0.30430 (13)0.07196 (11)0.0349 (3)
H5CA0.65520.32280.13460.052*
H5CB0.67920.33090.03050.052*
H5CC0.60730.22450.06320.052*
C5C0.43789 (14)0.32422 (13)0.04145 (9)0.0346 (3)
H6CA0.36380.36420.05270.052*
H6CB0.41600.24510.04470.052*
H6CC0.49330.34150.08730.052*
C6C0.27048 (11)0.15583 (10)0.26283 (8)0.0208 (2)
C7C0.11856 (12)0.09791 (10)0.36725 (9)0.0257 (3)
C8C0.07780 (17)0.01067 (13)0.31583 (12)0.0425 (4)
H9CA0.14920.04490.29570.064*
H9CB0.02090.00290.26310.064*
H9CC0.03710.05970.35570.064*
C9C0.21050 (15)0.08115 (13)0.44839 (10)0.0356 (3)
H10G0.28170.04720.42760.053*
H10H0.17250.03310.49040.053*
H10I0.23630.15230.47930.053*
C10C0.00908 (15)0.15331 (13)0.39930 (12)0.0402 (4)
H11G0.03660.22420.42990.060*
H11H0.03010.10640.44150.060*
H11I0.04960.16490.34700.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0203 (4)0.0274 (4)0.0250 (4)0.0057 (3)0.0033 (3)0.0002 (3)
O2A0.0208 (4)0.0459 (6)0.0339 (5)0.0082 (4)0.0026 (4)0.0038 (4)
N1A0.0158 (5)0.0186 (5)0.0244 (5)0.0027 (4)0.0026 (4)0.0020 (4)
N2A0.0144 (5)0.0250 (5)0.0287 (5)0.0030 (4)0.0003 (4)0.0006 (4)
N3A0.0208 (5)0.0224 (5)0.0246 (5)0.0050 (4)0.0040 (4)0.0009 (4)
N4A0.0171 (5)0.0221 (5)0.0249 (5)0.0052 (4)0.0035 (4)0.0010 (4)
N5A0.0155 (5)0.0280 (5)0.0297 (5)0.0044 (4)0.0032 (4)0.0028 (4)
C1A0.0166 (5)0.0164 (5)0.0266 (6)0.0031 (4)0.0036 (4)0.0045 (4)
C2A0.0208 (6)0.0157 (5)0.0247 (6)0.0026 (4)0.0038 (4)0.0037 (4)
C3A0.0217 (6)0.0226 (6)0.0280 (6)0.0032 (5)0.0073 (5)0.0004 (5)
C4A0.0333 (7)0.0283 (7)0.0341 (7)0.0140 (5)0.0036 (6)0.0015 (5)
C5A0.0368 (7)0.0288 (7)0.0272 (6)0.0071 (5)0.0069 (5)0.0009 (5)
C6A0.0160 (6)0.0211 (6)0.0332 (7)0.0050 (4)0.0022 (5)0.0036 (5)
C7A0.0173 (6)0.0293 (7)0.0365 (7)0.0057 (5)0.0075 (5)0.0044 (5)
C8A0.0201 (6)0.0352 (8)0.0571 (9)0.0007 (5)0.0088 (6)0.0016 (7)
C9A0.0255 (7)0.0365 (8)0.0501 (9)0.0132 (6)0.0109 (6)0.0102 (6)
C10A0.0283 (7)0.0515 (9)0.0388 (8)0.0049 (6)0.0124 (6)0.0011 (7)
O1B0.0264 (4)0.0276 (5)0.0227 (4)0.0022 (4)0.0015 (3)0.0088 (3)
O2B0.0252 (4)0.0241 (4)0.0314 (5)0.0006 (3)0.0015 (4)0.0074 (4)
N1B0.0200 (5)0.0179 (5)0.0230 (5)0.0025 (4)0.0027 (4)0.0027 (4)
N2B0.0236 (5)0.0193 (5)0.0302 (6)0.0007 (4)0.0045 (4)0.0040 (4)
N3B0.0222 (5)0.0221 (5)0.0220 (5)0.0042 (4)0.0005 (4)0.0051 (4)
N4B0.0208 (5)0.0220 (5)0.0205 (5)0.0020 (4)0.0003 (4)0.0052 (4)
N5B0.0237 (5)0.0282 (5)0.0249 (5)0.0014 (4)0.0011 (4)0.0062 (4)
C1B0.0211 (6)0.0202 (5)0.0214 (5)0.0038 (4)0.0051 (4)0.0017 (4)
C2B0.0222 (6)0.0177 (5)0.0231 (6)0.0054 (4)0.0024 (4)0.0024 (4)
C3B0.0265 (6)0.0220 (6)0.0286 (6)0.0036 (5)0.0052 (5)0.0040 (5)
C4B0.0259 (7)0.0384 (8)0.0491 (9)0.0114 (6)0.0060 (6)0.0020 (6)
C5B0.0417 (8)0.0307 (7)0.0311 (7)0.0070 (6)0.0101 (6)0.0026 (6)
C6B0.0212 (6)0.0212 (6)0.0219 (6)0.0026 (4)0.0029 (4)0.0006 (4)
C7B0.0317 (7)0.0334 (7)0.0396 (8)0.0063 (6)0.0143 (6)0.0074 (6)
C8B0.0243 (7)0.0490 (10)0.0815 (14)0.0017 (7)0.0040 (8)0.0148 (9)
C9B0.0708 (13)0.0385 (9)0.0495 (10)0.0147 (8)0.0227 (9)0.0014 (7)
C10B0.0620 (12)0.0555 (11)0.0538 (11)0.0152 (9)0.0334 (9)0.0199 (9)
O1C0.0243 (4)0.0211 (4)0.0284 (4)0.0056 (3)0.0095 (3)0.0046 (3)
O2C0.0361 (5)0.0217 (4)0.0348 (5)0.0100 (4)0.0133 (4)0.0084 (4)
N1C0.0209 (5)0.0180 (5)0.0207 (5)0.0024 (4)0.0038 (4)0.0036 (4)
N2C0.0261 (6)0.0181 (5)0.0265 (5)0.0040 (4)0.0047 (4)0.0066 (4)
N3C0.0222 (5)0.0221 (5)0.0240 (5)0.0036 (4)0.0085 (4)0.0023 (4)
N4C0.0205 (5)0.0195 (5)0.0213 (5)0.0038 (4)0.0060 (4)0.0036 (4)
N5C0.0254 (5)0.0197 (5)0.0252 (5)0.0052 (4)0.0074 (4)0.0081 (4)
C1C0.0199 (5)0.0187 (5)0.0187 (5)0.0009 (4)0.0006 (4)0.0027 (4)
C2C0.0204 (6)0.0198 (5)0.0202 (5)0.0017 (4)0.0022 (4)0.0003 (4)
C3C0.0261 (6)0.0207 (6)0.0245 (6)0.0005 (5)0.0091 (5)0.0019 (4)
C4C0.0281 (7)0.0365 (7)0.0432 (8)0.0047 (6)0.0152 (6)0.0083 (6)
C5C0.0383 (8)0.0413 (8)0.0243 (6)0.0086 (6)0.0101 (6)0.0004 (6)
C6C0.0244 (6)0.0193 (6)0.0189 (5)0.0021 (4)0.0016 (4)0.0045 (4)
C7C0.0281 (6)0.0231 (6)0.0281 (6)0.0027 (5)0.0094 (5)0.0098 (5)
C8C0.0496 (9)0.0309 (8)0.0464 (9)0.0112 (7)0.0099 (7)0.0037 (6)
C9C0.0412 (8)0.0385 (8)0.0292 (7)0.0065 (6)0.0063 (6)0.0150 (6)
C10C0.0350 (8)0.0403 (8)0.0512 (9)0.0100 (6)0.0222 (7)0.0198 (7)
Geometric parameters (Å, º) top
O1A—C1A1.2329 (15)C4B—H5BA0.9800
O2A—C6A1.2061 (16)C4B—H5BB0.9800
N1A—C1A1.3725 (15)C4B—H5BC0.9800
N1A—C2A1.3764 (16)C5B—H6BA0.9800
N1A—N2A1.4028 (14)C5B—H6BB0.9800
N2A—H3N10.904 (19)C5B—H6BC0.9800
N2A—H3N20.91 (2)C7B—C10B1.525 (2)
N3A—C2A1.2971 (16)C7B—C8B1.530 (3)
N3A—N4A1.4004 (14)C7B—C9B1.532 (2)
N4A—C1A1.3757 (16)C8B—H9BA0.9800
N4A—C6A1.4435 (15)C8B—H9BB0.9800
N5A—C6A1.3398 (17)C8B—H9BC0.9800
N5A—C7A1.4879 (15)C9B—H10D0.9800
N5A—H4AB0.8800C9B—H10E0.9800
C2A—C3A1.4959 (16)C9B—H10F0.9800
C3A—C5A1.5271 (19)C10B—H11D0.9800
C3A—C4A1.5346 (18)C10B—H11E0.9800
C3A—H4AA1.0000C10B—H11F0.9800
C4A—H5AA0.9800O1C—C1C1.2278 (15)
C4A—H5AB0.9800O2C—C6C1.2103 (16)
C4A—H5AC0.9800N1C—C1C1.3717 (15)
C5A—H6AA0.9800N1C—C2C1.3746 (16)
C5A—H6AB0.9800N1C—N2C1.4072 (14)
C5A—H6AC0.9800N2C—H3C20.906 (18)
C7A—C10A1.524 (2)N2C—H3C10.88 (2)
C7A—C8A1.524 (2)N3C—C2C1.2926 (16)
C7A—C9A1.5276 (19)N3C—N4C1.3967 (14)
C8A—H9AA0.9800N4C—C1C1.3764 (15)
C8A—H9AB0.9800N4C—C6C1.4373 (15)
C8A—H9AC0.9800N5C—C6C1.3358 (16)
C9A—H10A0.9800N5C—C7C1.4802 (15)
C9A—H10B0.9800N5C—H4CB0.8800
C9A—H10C0.9800C2C—C3C1.4972 (16)
C10A—H11A0.9800C3C—C4C1.5224 (19)
C10A—H11B0.9800C3C—C5C1.5298 (19)
C10A—H11C0.9800C3C—H4CA1.0000
O1B—C1B1.2301 (15)C4C—H5CA0.9800
O2B—C6B1.2161 (15)C4C—H5CB0.9800
N1B—C1B1.3713 (16)C4C—H5CC0.9800
N1B—C2B1.3750 (15)C5C—H6CA0.9800
N1B—N2B1.4044 (14)C5C—H6CB0.9800
N2B—H3B20.929 (19)C5C—H6CC0.9800
N2B—H3B10.89 (2)C7C—C9C1.5243 (19)
N3B—C2B1.2973 (17)C7C—C8C1.525 (2)
N3B—N4B1.3974 (14)C7C—C10C1.5258 (19)
N4B—C1B1.3794 (16)C8C—H9CA0.9800
N4B—C6B1.4270 (16)C8C—H9CB0.9800
N5B—C6B1.3380 (16)C8C—H9CC0.9800
N5B—C7B1.4771 (17)C9C—H10G0.9800
N5B—H4BB0.8800C9C—H10H0.9800
C2B—C3B1.4948 (17)C9C—H10I0.9800
C3B—C4B1.526 (2)C10C—H11G0.9800
C3B—C5B1.5306 (19)C10C—H11H0.9800
C3B—H4BA1.0000C10C—H11I0.9800
C1A—N1A—C2A109.01 (10)C3B—C5B—H6BB109.5
C1A—N1A—N2A126.31 (10)H6BA—C5B—H6BB109.5
C2A—N1A—N2A124.69 (10)C3B—C5B—H6BC109.5
N1A—N2A—H3N1107.3 (11)H6BA—C5B—H6BC109.5
N1A—N2A—H3N2109.0 (12)H6BB—C5B—H6BC109.5
H3N1—N2A—H3N2114.1 (16)O2B—C6B—N5B127.90 (12)
C2A—N3A—N4A104.12 (10)O2B—C6B—N4B119.55 (11)
C1A—N4A—N3A112.25 (9)N5B—C6B—N4B112.54 (10)
C1A—N4A—C6A129.36 (10)N5B—C7B—C10B105.72 (13)
N3A—N4A—C6A118.27 (10)N5B—C7B—C8B109.22 (13)
C6A—N5A—C7A123.99 (11)C10B—C7B—C8B110.02 (16)
C6A—N5A—H4AB118.0N5B—C7B—C9B110.28 (14)
C7A—N5A—H4AB118.0C10B—C7B—C9B110.52 (15)
O1A—C1A—N1A127.90 (11)C8B—C7B—C9B110.95 (15)
O1A—C1A—N4A129.20 (11)C7B—C8B—H9BA109.5
N1A—C1A—N4A102.90 (10)C7B—C8B—H9BB109.5
N3A—C2A—N1A111.70 (10)H9BA—C8B—H9BB109.5
N3A—C2A—C3A125.55 (11)C7B—C8B—H9BC109.5
N1A—C2A—C3A122.66 (11)H9BA—C8B—H9BC109.5
C2A—C3A—C5A111.00 (11)H9BB—C8B—H9BC109.5
C2A—C3A—C4A109.25 (10)C7B—C9B—H10D109.5
C5A—C3A—C4A111.24 (11)C7B—C9B—H10E109.5
C2A—C3A—H4AA108.4H10D—C9B—H10E109.5
C5A—C3A—H4AA108.4C7B—C9B—H10F109.5
C4A—C3A—H4AA108.4H10D—C9B—H10F109.5
C3A—C4A—H5AA109.5H10E—C9B—H10F109.5
C3A—C4A—H5AB109.5C7B—C10B—H11D109.5
H5AA—C4A—H5AB109.5C7B—C10B—H11E109.5
C3A—C4A—H5AC109.5H11D—C10B—H11E109.5
H5AA—C4A—H5AC109.5C7B—C10B—H11F109.5
H5AB—C4A—H5AC109.5H11D—C10B—H11F109.5
C3A—C5A—H6AA109.5H11E—C10B—H11F109.5
C3A—C5A—H6AB109.5C1C—N1C—C2C109.08 (10)
H6AA—C5A—H6AB109.5C1C—N1C—N2C125.18 (10)
C3A—C5A—H6AC109.5C2C—N1C—N2C125.58 (10)
H6AA—C5A—H6AC109.5N1C—N2C—H3C2104.3 (11)
H6AB—C5A—H6AC109.5N1C—N2C—H3C1108.9 (12)
O2A—C6A—N5A128.31 (12)H3C2—N2C—H3C1105.8 (17)
O2A—C6A—N4A119.58 (12)C2C—N3C—N4C104.58 (10)
N5A—C6A—N4A112.11 (11)C1C—N4C—N3C111.95 (9)
N5A—C7A—C10A105.80 (11)C1C—N4C—C6C128.99 (10)
N5A—C7A—C8A110.33 (11)N3C—N4C—C6C118.94 (10)
C10A—C7A—C8A109.89 (12)C6C—N5C—C7C123.83 (10)
N5A—C7A—C9A109.66 (11)C6C—N5C—H4CB118.1
C10A—C7A—C9A109.83 (12)C7C—N5C—H4CB118.1
C8A—C7A—C9A111.18 (12)O1C—C1C—N1C127.35 (11)
C7A—C8A—H9AA109.5O1C—C1C—N4C129.76 (11)
C7A—C8A—H9AB109.5N1C—C1C—N4C102.87 (10)
H9AA—C8A—H9AB109.5N3C—C2C—N1C111.48 (10)
C7A—C8A—H9AC109.5N3C—C2C—C3C125.19 (11)
H9AA—C8A—H9AC109.5N1C—C2C—C3C123.25 (11)
H9AB—C8A—H9AC109.5C2C—C3C—C4C111.38 (11)
C7A—C9A—H10A109.5C2C—C3C—C5C108.67 (10)
C7A—C9A—H10B109.5C4C—C3C—C5C112.05 (12)
H10A—C9A—H10B109.5C2C—C3C—H4CA108.2
C7A—C9A—H10C109.5C4C—C3C—H4CA108.2
H10A—C9A—H10C109.5C5C—C3C—H4CA108.2
H10B—C9A—H10C109.5C3C—C4C—H5CA109.5
C7A—C10A—H11A109.5C3C—C4C—H5CB109.5
C7A—C10A—H11B109.5H5CA—C4C—H5CB109.5
H11A—C10A—H11B109.5C3C—C4C—H5CC109.5
C7A—C10A—H11C109.5H5CA—C4C—H5CC109.5
H11A—C10A—H11C109.5H5CB—C4C—H5CC109.5
H11B—C10A—H11C109.5C3C—C5C—H6CA109.5
C1B—N1B—C2B108.91 (10)C3C—C5C—H6CB109.5
C1B—N1B—N2B124.54 (10)H6CA—C5C—H6CB109.5
C2B—N1B—N2B125.57 (10)C3C—C5C—H6CC109.5
N1B—N2B—H3B2107.8 (11)H6CA—C5C—H6CC109.5
N1B—N2B—H3B1106.6 (12)H6CB—C5C—H6CC109.5
H3B2—N2B—H3B1110.3 (16)O2C—C6C—N5C128.46 (11)
C2B—N3B—N4B104.24 (10)O2C—C6C—N4C119.36 (11)
C1B—N4B—N3B112.05 (10)N5C—C6C—N4C112.16 (10)
C1B—N4B—C6B129.10 (10)N5C—C7C—C9C109.05 (11)
N3B—N4B—C6B118.67 (10)N5C—C7C—C8C110.71 (11)
C6B—N5B—C7B124.13 (11)C9C—C7C—C8C111.28 (12)
C6B—N5B—H4BB117.9N5C—C7C—C10C105.50 (10)
C7B—N5B—H4BB117.9C9C—C7C—C10C109.49 (12)
O1B—C1B—N1B127.81 (11)C8C—C7C—C10C110.63 (13)
O1B—C1B—N4B129.22 (11)C7C—C8C—H9CA109.5
N1B—C1B—N4B102.95 (10)C7C—C8C—H9CB109.5
N3B—C2B—N1B111.74 (11)H9CA—C8C—H9CB109.5
N3B—C2B—C3B123.07 (11)C7C—C8C—H9CC109.5
N1B—C2B—C3B125.18 (11)H9CA—C8C—H9CC109.5
C2B—C3B—C4B112.37 (11)H9CB—C8C—H9CC109.5
C2B—C3B—C5B110.69 (11)C7C—C9C—H10G109.5
C4B—C3B—C5B111.95 (12)C7C—C9C—H10H109.5
C2B—C3B—H4BA107.2H10G—C9C—H10H109.5
C4B—C3B—H4BA107.2C7C—C9C—H10I109.5
C5B—C3B—H4BA107.2H10G—C9C—H10I109.5
C3B—C4B—H5BA109.5H10H—C9C—H10I109.5
C3B—C4B—H5BB109.5C7C—C10C—H11G109.5
H5BA—C4B—H5BB109.5C7C—C10C—H11H109.5
C3B—C4B—H5BC109.5H11G—C10C—H11H109.5
H5BA—C4B—H5BC109.5C7C—C10C—H11I109.5
H5BB—C4B—H5BC109.5H11G—C10C—H11I109.5
C3B—C5B—H6BA109.5H11H—C10C—H11I109.5
C2A—N3A—N4A—C1A0.10 (13)N2B—N1B—C2B—C3B6.47 (19)
C2A—N3A—N4A—C6A176.55 (10)N3B—C2B—C3B—C4B120.86 (14)
C2A—N1A—C1A—O1A178.86 (12)N1B—C2B—C3B—C4B60.80 (16)
N2A—N1A—C1A—O1A0.90 (19)N3B—C2B—C3B—C5B113.15 (14)
C2A—N1A—C1A—N4A0.84 (12)N1B—C2B—C3B—C5B65.18 (17)
N2A—N1A—C1A—N4A179.39 (10)C7B—N5B—C6B—O2B6.4 (2)
N3A—N4A—C1A—O1A179.11 (11)C7B—N5B—C6B—N4B174.12 (12)
C6A—N4A—C1A—O1A3.2 (2)C1B—N4B—C6B—O2B179.99 (12)
N3A—N4A—C1A—N1A0.59 (12)N3B—N4B—C6B—O2B5.26 (17)
C6A—N4A—C1A—N1A176.55 (11)C1B—N4B—C6B—N5B0.45 (18)
N4A—N3A—C2A—N1A0.46 (13)N3B—N4B—C6B—N5B175.21 (10)
N4A—N3A—C2A—C3A176.14 (11)C6B—N5B—C7B—C10B177.48 (15)
C1A—N1A—C2A—N3A0.86 (13)C6B—N5B—C7B—C8B64.18 (17)
N2A—N1A—C2A—N3A179.37 (10)C6B—N5B—C7B—C9B57.99 (19)
C1A—N1A—C2A—C3A175.85 (10)C2C—N3C—N4C—C1C1.08 (13)
N2A—N1A—C2A—C3A3.92 (17)C2C—N3C—N4C—C6C175.35 (10)
N3A—C2A—C3A—C5A11.65 (17)C2C—N1C—C1C—O1C179.41 (12)
N1A—C2A—C3A—C5A172.11 (11)N2C—N1C—C1C—O1C3.8 (2)
N3A—C2A—C3A—C4A111.38 (14)C2C—N1C—C1C—N4C1.73 (12)
N1A—C2A—C3A—C4A64.86 (15)N2C—N1C—C1C—N4C177.36 (10)
C7A—N5A—C6A—O2A1.1 (2)N3C—N4C—C1C—O1C179.44 (12)
C7A—N5A—C6A—N4A178.68 (11)C6C—N4C—C1C—O1C4.6 (2)
C1A—N4A—C6A—O2A178.10 (12)N3C—N4C—C1C—N1C1.74 (13)
N3A—N4A—C6A—O2A6.15 (17)C6C—N4C—C1C—N1C174.23 (11)
C1A—N4A—C6A—N5A2.10 (18)N4C—N3C—C2C—N1C0.09 (13)
N3A—N4A—C6A—N5A173.65 (10)N4C—N3C—C2C—C3C177.01 (11)
C6A—N5A—C7A—C10A175.58 (12)C1C—N1C—C2C—N3C1.21 (14)
C6A—N5A—C7A—C8A56.76 (17)N2C—N1C—C2C—N3C176.81 (11)
C6A—N5A—C7A—C9A66.03 (16)C1C—N1C—C2C—C3C178.20 (11)
C2B—N3B—N4B—C1B0.70 (13)N2C—N1C—C2C—C3C6.20 (18)
C2B—N3B—N4B—C6B176.31 (10)N3C—C2C—C3C—C4C35.08 (17)
C2B—N1B—C1B—O1B178.39 (12)N1C—C2C—C3C—C4C148.34 (12)
N2B—N1B—C1B—O1B9.2 (2)N3C—C2C—C3C—C5C88.83 (15)
C2B—N1B—C1B—N4B3.08 (12)N1C—C2C—C3C—C5C87.75 (14)
N2B—N1B—C1B—N4B172.31 (10)C7C—N5C—C6C—O2C5.9 (2)
N3B—N4B—C1B—O1B179.14 (12)C7C—N5C—C6C—N4C175.50 (11)
C6B—N4B—C1B—O1B4.1 (2)C1C—N4C—C6C—O2C178.93 (12)
N3B—N4B—C1B—N1B2.37 (13)N3C—N4C—C6C—O2C3.20 (17)
C6B—N4B—C1B—N1B177.41 (11)C1C—N4C—C6C—N5C0.15 (18)
N4B—N3B—C2B—N1B1.35 (13)N3C—N4C—C6C—N5C175.58 (10)
N4B—N3B—C2B—C3B177.19 (11)C6C—N5C—C7C—C9C64.87 (16)
C1B—N1B—C2B—N3B2.95 (14)C6C—N5C—C7C—C8C57.90 (17)
N2B—N1B—C2B—N3B172.03 (11)C6C—N5C—C7C—C10C177.61 (13)
C1B—N1B—C2B—C3B175.55 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H3N1···O1C0.904 (19)2.220 (19)3.0832 (14)159.6 (15)
N2A—H3N2···N3B0.91 (2)2.40 (2)3.2251 (15)150.9 (15)
N2A—H3N2···O2B0.91 (2)2.483 (19)3.2492 (14)141.7 (15)
N5A—H4AB···O1A0.882.052.7770 (14)140
N2B—H3B2···N3Ci0.929 (19)2.233 (19)3.1619 (15)179.1 (15)
N2B—H3B1···O1Bii0.89 (2)2.27 (2)3.1356 (15)163.1 (16)
N5B—H4BB···O1B0.882.042.7655 (14)139
N2C—H3C2···O1A0.906 (18)2.171 (18)2.9455 (15)143.1 (15)
N2C—H3C1···O2B0.88 (2)2.41 (2)3.0718 (14)132.8 (16)
N5C—H4CB···O1C0.882.052.7721 (13)139
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z.

Experimental details

Crystal data
Chemical formulaC10H19N5O2
Mr241.30
Crystal system, space groupTriclinic, P1
Temperature (K)123
a, b, c (Å)11.0298 (2), 12.2135 (4), 14.8542 (4)
α, β, γ (°)92.244 (2), 95.7020 (19), 93.379 (2)
V3)1985.65 (9)
Z6
Radiation typeCu Kα
µ (mm1)0.72
Crystal size (mm)0.35 × 0.25 × 0.15
Data collection
DiffractometerAgilent Xcalibur (Ruby, Gemini)
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
Tmin, Tmax0.791, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
13380, 7959, 7592
Rint0.019
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.115, 1.05
No. of reflections7959
No. of parameters499
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.28

Computer programs: CrysAlis PRO (Agilent, 2012), CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H3N1···O1C0.904 (19)2.220 (19)3.0832 (14)159.6 (15)
N2A—H3N2···N3B0.91 (2)2.40 (2)3.2251 (15)150.9 (15)
N2A—H3N2···O2B0.91 (2)2.483 (19)3.2492 (14)141.7 (15)
N5A—H4AB···O1A0.882.052.7770 (14)139.8
N2B—H3B2···N3Ci0.929 (19)2.233 (19)3.1619 (15)179.1 (15)
N2B—H3B1···O1Bii0.89 (2)2.27 (2)3.1356 (15)163.1 (16)
N5B—H4BB···O1B0.882.042.7655 (14)139.2
N2C—H3C2···O1A0.906 (18)2.171 (18)2.9455 (15)143.1 (15)
N2C—H3C1···O2B0.88 (2)2.41 (2)3.0718 (14)132.8 (16)
N5C—H4CB···O1C0.882.052.7721 (13)139.1
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+2, z.
 

Acknowledgements

MK thanks the UOM for research facilities. RJB acknowledges the NSF–MRI program (grant No. CHE-0619278) for funds to purchase the X-ray diffractometer.

References

First citationAgilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
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First citationCrockett, R., Forrester, A. R. & Howie, R. A. (2004). Acta Cryst. E60, o460–o461.  Web of Science CSD CrossRef IUCr Journals
First citationDayan, F. E., Trindade, M. L. B. & Velini, E. D. (2009). Weed Sci. 57, 579–583.  Web of Science CrossRef CAS
First citationDiehr (1998). US Patent No. US005708184A.
First citationDupont, L., Englebert, S., Dideberg, O., Pirotte, B. & Delarge, J. (1991). Acta Cryst. C47, 1557–1559.  CSD CrossRef CAS Web of Science IUCr Journals
First citationHeng, J., Zhu, H.-J., Tang, Q.-G. & Yan, H.-L. (2006). Acta Cryst. E62, o3111–o3112.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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