organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

Crystal structure of dimeth­yl[(E)-2-(1-methyl-5-nitro-1H-imidazol-4-yl)ethen­yl]amine

aUral Federal University, Mira 19 Ekaterinburg 620002, Russian Federation, and bPostovsky Institute of Organic Synthesis, Kovalevskoy 22 Ekaterinburg 620090, Russian Federation
*Correspondence e-mail: n.a.beliaev@urfu.ru

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 15 December 2015; accepted 29 December 2015; online 23 January 2016)

The title compound, C8H12N4O2, crystallized with two independent mol­ecules in the asymmetric unit. The bonds lengths of the enamine moiety show strong conjugation in the N—C=C system. In the crystal, the two independent mol­ecules are linked by C—H⋯O hydrogen bonds, forming zigzag chains along [10-1]. The chains are linked by further C—H⋯O hydrogen bonds, forming layers parallel to the ac plane.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title enamine was synthesized for the study of the [3 + 2] cyclo­addition reactions with azides (Bakulev et al., 2012[Bakulev, V. A., Efimov, I. V., Belyaev, N. A., Rozin, Yu. A., Volkova, N. N. & El'tsov, O. S. (2012). Chem. Heterocycl. Compd. 47, 1593-1595.]) and hydroxamoylchlorides (Bakulev et al., 2013[Bakulev, V. A., Efimov, I. V., Belyaev, N. A., Zhidovinov, S. S., Rozin, Y. A., Volkova, N. N., Khabarova, A. A. & Ele'tsov, O. S. (2013). Chem. Heterocycl. Compd. 48, 1880-1882.]). It crystallized with two independent mol­ecules in the asymmetric unit, Fig. 1[link]. Both mol­ecules are relatively planar. The mean plane of the N,N-di­methyl­ethenamine group N2/C3/C6–C8 is inclined to the imidazole ring N1/N3/C1/C4/C5 by 2.16 (11)°, while the mean plane of the N,N-di­methyl­ethenamine group N2A/C3A/C6A–C8A is inclined to the imidazole ring NA1/N3A/C1A/C4A/C5A by 6.17 (12)°. The NO2 group is inclined to the imidazole ring by 8.2 (2)° for ring N1/N3/C1/C4/C5 vs. N4/O1/O2, and 5.0 (2)° for ring N1A/N3A/C1A/C4A/C5A vs. N4A/O1A/O2A. The substituents at the C3=C8 and C3A=C8A bonds are placed in trans-positions. The bonds lengths of the enamine moiety show strong conjugation in the N—C=C system. The N—C bond lengths and C=C bond lengths in the two mol­ecules are very similar: N2—C8 is 1.326 (2) and N2A—C8A 1.331 (2) Å, and C8=C3 is 1.342 (3) and C8A=C3A is 1.334 (2) Å.

[Figure 1]
Figure 1
A view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

In the crystal, the two independent mol­ecules are linked by C—H⋯O hydrogen bonds, forming zigzag chains along [10[\overline{1}]]. The chains are linked by further C—H⋯O hydrogen bonds, forming layers parallel to the ac plane; see Fig. 2[link] and Table 1[link].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O1Ai 0.954 (15) 2.399 (15) 3.235 (3) 146 (1)
C2A—H2A⋯O1ii 0.958 (16) 2.254 (15) 3.181 (3) 162 (1)
C6—H6B⋯O1Aiii 0.96 2.58 3.461 (3) 153
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) -x+1, -y, -z+1.
[Figure 2]
Figure 2
A view along the c axis of the crystal packing of the title compound. Hydrogen bonds are drawn as dashed lines (see Table 1[link]), and H atoms not involved in these inter­actions have been omitted for clarity.

Synthesis and crystallization

The title compound was synthesized from 1,4-dimethyl-5-nitro-1H-imidazole following a reported procedure (Hosmane et al., 1985[Hosmane, R. S., Bhan, A. & Rauser, M. E. (1985). J. Org. Chem. 50, 5892-5895.]), illustrated in Fig. 3[link], and crystallized from ethanol yielding dark-red prismatic crystals.

[Figure 3]
Figure 3
Reaction scheme.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C8H12N4O2
Mr 196.22
Crystal system, space group Monoclinic, P21/c
Temperature (K) 295
a, b, c (Å) 10.5015 (12), 23.561 (3), 7.7533 (6)
β (°) 96.604 (8)
V3) 1905.6 (3)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.25 × 0.20 × 0.15
 
Data collection
Diffractometer Oxford Diffraction Xcalibur S CCD
No. of measured, independent and observed [I > 2σ(I)] reflections 10647, 3875, 1523
Rint 0.038
(sin θ/λ)max−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.066, 1.00
No. of reflections 3875
No. of parameters 284
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.14, −0.12
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, England.]), CrysAlis RED (Oxford Diffraction, 2006[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd., Abingdon, England.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Experimental top

The title compound was synthesized from 1,4-dimethyl-5-nitro-1H-imidazole following a reported procedure (Hosmane et al., 1985), illustrated in Fig. 3, and crystallized from ethanol yielding red prismatic crystals.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The methyl H atoms were included in calculated positions and treated as riding: C—H = 0.96 Å with Uiso(H) = 1.5Ueq(C-methyl). The remainder of the H atoms were located in a difference Fourier map and freely refined.

Structure description top

The title enamine was synthesized for the study of the [3 + 2] cycloaddition reactions with azides (Bakulev et al., 2012) and hydroxamoylchlorides (Bakulev et al., 2013). It crystallized with two independent molecules in the asymmetric unit, Fig. 1. Both molecules are relatively planar. The mean plane of the N,N-dimethylethenamine group N2/C3/C6–C8 is inclined to the imidazole ring N1/N3/C1/C4/C5 by 2.16 (11)°, while the mean plane of the N,N-dimethylethenamine group N2A/C3A/C6A–C8A is inclined to the imidazole ring NA1/N3A/C1A/C4A/C5A by 6.17 (12)°. The NO2 group is inclined to the imidazole ring by 8.2 (2)° for ring N1/N3/C1/C4/C5 vs. N4/O1/O2, and 5.0 (2)° for ring N1A/N3A/C1A/C4A/C5A versus. N4A/O1A/O2A. The substituents at the C3C8 and C3AC8A bonds are placed in trans-positions. The bonds lengths of the enamine moiety show strong conjugation in the N—C=C system. The N—C bond lengths and CC bond lengths in the two molecules are very similar: N2—C8 is 1.326 (2) and N2A—C8A 1.331 (2) Å, and C8C3 is 1.342 (3) and C8AC3A is 1.334 (2) Å.

In the crystal, the two independent molecules are linked by C—H···O hydrogen bonds, forming zigzag chains along [101]. The chains are linked by further C—H···O hydrogen bonds, forming layers parallel to the ac plane; see Fig. 2 and Table 1.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); 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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view along the c axis of the crystal packing of the title compound. Hydrogen bonds are drawn as dashed lines (see Table 1), and H atoms not involved in these interactions have been omitted for clarity.
[Figure 3] Fig. 3. Reaction scheme.
Dimethyl[(E)-2-(1-methyl-5-nitro-1H-imidazol-4-yl)ethenyl]amine top
Crystal data top
C8H12N4O2F(000) = 832
Mr = 196.22Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1523 reflections
a = 10.5015 (12) Åθ = 2.8–26.4°
b = 23.561 (3) ŵ = 0.10 mm1
c = 7.7533 (6) ÅT = 295 K
β = 96.604 (8)°Prism, red
V = 1905.6 (3) Å30.25 × 0.20 × 0.15 mm
Z = 8
Data collection top
Oxford Diffraction Xcalibur S CCD
diffractometer
1523 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 26.4°, θmin = 2.8°
ω scansh = 1313
10647 measured reflectionsk = 2829
3875 independent reflectionsl = 96
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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.066 w = 1/[σ2(Fo2) + (0.016P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3875 reflectionsΔρmax = 0.14 e Å3
284 parametersΔρmin = 0.12 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00217 (15)
Crystal data top
C8H12N4O2V = 1905.6 (3) Å3
Mr = 196.22Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.5015 (12) ŵ = 0.10 mm1
b = 23.561 (3) ÅT = 295 K
c = 7.7533 (6) Å0.25 × 0.20 × 0.15 mm
β = 96.604 (8)°
Data collection top
Oxford Diffraction Xcalibur S CCD
diffractometer
1523 reflections with I > 2σ(I)
10647 measured reflectionsRint = 0.038
3875 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.066H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.14 e Å3
3875 reflectionsΔρmin = 0.12 e Å3
284 parameters
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
N10.44977 (16)0.40312 (6)0.2065 (2)0.0497 (5)
N1A1.04292 (17)0.01495 (7)0.7905 (2)0.0531 (5)
O1A0.80215 (14)0.03162 (6)0.6211 (2)0.0983 (6)
C1A1.02942 (19)0.07638 (7)0.7864 (2)0.0718 (6)
H1AA1.10080.09330.85640.108*
H1AB1.02730.08950.66890.108*
H1AC0.95120.08690.83120.108*
O2A0.78287 (14)0.05713 (6)0.56123 (18)0.0818 (5)
N2A1.02826 (16)0.23407 (8)0.7367 (2)0.0608 (5)
C2A1.1448 (2)0.01246 (9)0.8654 (3)0.0615 (6)
N3A1.14002 (15)0.06755 (7)0.8499 (2)0.0587 (5)
C3A0.9826 (2)0.13453 (8)0.7150 (3)0.0510 (6)
C4A1.02459 (18)0.07855 (7)0.7556 (2)0.0454 (5)
N4A0.84503 (18)0.01685 (7)0.6297 (2)0.0619 (5)
C5A0.96365 (19)0.02736 (8)0.7181 (2)0.0471 (5)
C6A1.12128 (19)0.27801 (8)0.7863 (3)0.0796 (7)
H6AA1.19920.26110.83940.119*
H6AB1.08810.30330.86720.119*
H6AC1.13840.29880.68500.119*
C7A0.9047 (2)0.25138 (8)0.6542 (3)0.0795 (8)
H7AA0.83880.23480.71400.119*
H7AB0.89470.23890.53550.119*
H7AC0.89810.29200.65800.119*
C8A1.0565 (2)0.17934 (9)0.7605 (3)0.0511 (6)
O10.66579 (13)0.42352 (6)0.43092 (17)0.0828 (5)
C10.46003 (19)0.46466 (8)0.2120 (2)0.0690 (7)
H1A0.39080.48100.13650.104*
H1B0.54020.47600.17450.104*
H1C0.45590.47760.32860.104*
O20.71826 (12)0.33445 (6)0.43022 (17)0.0716 (4)
N20.49194 (15)0.15456 (7)0.21675 (19)0.0565 (5)
C20.3544 (2)0.37399 (10)0.1211 (3)0.0557 (6)
N30.36672 (15)0.31899 (7)0.12659 (19)0.0540 (5)
C30.5290 (2)0.25429 (8)0.2591 (3)0.0490 (6)
C40.48305 (17)0.30967 (7)0.2234 (2)0.0436 (5)
N40.64519 (17)0.37394 (7)0.3824 (2)0.0553 (5)
C50.53483 (19)0.36189 (8)0.2743 (2)0.0440 (5)
C60.4020 (2)0.11081 (8)0.1539 (3)0.0760 (7)
H6A0.33690.12680.07100.114*
H6B0.36300.09520.24950.114*
H6C0.44630.08130.09950.114*
C70.60698 (19)0.13755 (8)0.3232 (2)0.0726 (7)
H7A0.68030.15290.27590.109*
H7B0.61250.09690.32540.109*
H7C0.60490.15150.43910.109*
C80.4624 (2)0.20899 (9)0.1940 (3)0.0494 (6)
H20.2798 (15)0.3923 (6)0.0652 (19)0.048 (5)*
H2A1.2150 (16)0.0078 (6)0.927 (2)0.064 (6)*
H8A1.1417 (15)0.1740 (6)0.8116 (19)0.057 (6)*
H3A0.9011 (15)0.1399 (6)0.6555 (19)0.054 (6)*
H80.3814 (15)0.2149 (6)0.1173 (19)0.049 (5)*
H30.6049 (15)0.2509 (6)0.3238 (19)0.053 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0538 (11)0.0434 (11)0.0506 (11)0.0017 (10)0.0003 (9)0.0025 (9)
N1A0.0560 (12)0.0434 (11)0.0594 (12)0.0008 (10)0.0038 (10)0.0030 (9)
O1A0.0962 (13)0.0684 (10)0.1209 (14)0.0340 (9)0.0282 (10)0.0003 (10)
C1A0.0934 (17)0.0440 (14)0.0788 (16)0.0007 (12)0.0138 (13)0.0044 (13)
O2A0.0665 (10)0.0818 (11)0.0895 (12)0.0025 (9)0.0231 (9)0.0131 (9)
N2A0.0581 (13)0.0494 (12)0.0741 (13)0.0052 (10)0.0046 (11)0.0024 (10)
C2A0.0515 (15)0.0555 (16)0.0745 (17)0.0045 (13)0.0050 (13)0.0077 (14)
N3A0.0482 (11)0.0517 (11)0.0727 (12)0.0015 (9)0.0082 (9)0.0051 (10)
C3A0.0460 (16)0.0481 (15)0.0568 (15)0.0001 (12)0.0038 (13)0.0024 (11)
C4A0.0420 (13)0.0476 (13)0.0464 (13)0.0023 (11)0.0045 (11)0.0032 (11)
N4A0.0610 (14)0.0622 (13)0.0594 (13)0.0089 (11)0.0062 (11)0.0008 (11)
C5A0.0440 (13)0.0477 (14)0.0483 (14)0.0026 (12)0.0003 (11)0.0006 (11)
C6A0.0816 (17)0.0568 (15)0.1014 (18)0.0096 (13)0.0145 (15)0.0051 (13)
C7A0.0725 (18)0.0775 (18)0.0875 (17)0.0255 (13)0.0043 (15)0.0161 (13)
C8A0.0484 (15)0.0473 (15)0.0570 (15)0.0094 (12)0.0035 (12)0.0023 (12)
O10.0893 (12)0.0601 (9)0.0920 (12)0.0178 (8)0.0203 (9)0.0156 (9)
C10.0809 (16)0.0462 (14)0.0779 (16)0.0007 (11)0.0001 (13)0.0059 (12)
O20.0562 (9)0.0739 (10)0.0796 (10)0.0090 (8)0.0139 (8)0.0015 (8)
N20.0629 (12)0.0424 (12)0.0633 (12)0.0028 (9)0.0032 (10)0.0003 (10)
C20.0483 (15)0.0629 (16)0.0535 (15)0.0034 (13)0.0048 (12)0.0048 (13)
N30.0531 (11)0.0482 (11)0.0583 (11)0.0049 (8)0.0036 (9)0.0007 (9)
C30.0437 (15)0.0555 (16)0.0470 (14)0.0015 (12)0.0013 (12)0.0002 (12)
C40.0455 (14)0.0485 (13)0.0363 (12)0.0022 (11)0.0030 (10)0.0028 (11)
N40.0538 (12)0.0571 (13)0.0534 (12)0.0025 (10)0.0000 (10)0.0006 (10)
C50.0425 (13)0.0466 (14)0.0413 (13)0.0020 (11)0.0014 (11)0.0022 (11)
C60.0903 (18)0.0578 (15)0.0823 (16)0.0160 (13)0.0199 (15)0.0092 (13)
C70.0865 (18)0.0634 (16)0.0663 (15)0.0184 (12)0.0015 (14)0.0055 (12)
C80.0527 (15)0.0493 (15)0.0463 (14)0.0022 (12)0.0061 (12)0.0010 (11)
Geometric parameters (Å, º) top
N1—C21.327 (2)C7A—H7AB0.9600
N1—C51.382 (2)C7A—H7AC0.9600
N1—C11.4543 (19)C8A—H8A0.944 (14)
N1A—C2A1.325 (2)O1—N41.2387 (17)
N1A—C5A1.376 (2)C1—H1A0.9600
N1A—C1A1.4544 (19)C1—H1B0.9600
O1A—N4A1.2264 (17)C1—H1C0.9600
C1A—H1AA0.9600O2—N41.2355 (17)
C1A—H1AB0.9600N2—C81.326 (2)
C1A—H1AC0.9600N2—C71.4393 (19)
O2A—N4A1.2365 (17)N2—C61.444 (2)
N2A—C8A1.331 (2)C2—N31.303 (2)
N2A—C7A1.438 (2)C2—H20.954 (14)
N2A—C6A1.445 (2)N3—C41.3760 (19)
C2A—N3A1.304 (2)C3—C81.342 (2)
C2A—H2A0.959 (15)C3—C41.408 (2)
N3A—C4A1.3665 (19)C3—H30.895 (14)
C3A—C8A1.334 (2)C4—C51.384 (2)
C3A—C4A1.415 (2)N4—C51.379 (2)
C3A—H3A0.933 (14)C6—H6A0.9600
C4A—C5A1.380 (2)C6—H6B0.9600
N4A—C5A1.374 (2)C6—H6C0.9600
C6A—H6AA0.9600C7—H7A0.9600
C6A—H6AB0.9600C7—H7B0.9600
C6A—H6AC0.9600C7—H7C0.9600
C7A—H7AA0.9600C8—H80.990 (14)
C2—N1—C5104.14 (17)N2A—C8A—C3A128.1 (2)
C2—N1—C1125.41 (17)N2A—C8A—H8A111.9 (9)
C5—N1—C1130.33 (17)C3A—C8A—H8A120.0 (9)
C2A—N1A—C5A104.22 (18)N1—C1—H1A109.5
C2A—N1A—C1A124.50 (17)N1—C1—H1B109.5
C5A—N1A—C1A131.23 (18)H1A—C1—H1B109.5
N1A—C1A—H1AA109.5N1—C1—H1C109.5
N1A—C1A—H1AB109.5H1A—C1—H1C109.5
H1AA—C1A—H1AB109.5H1B—C1—H1C109.5
N1A—C1A—H1AC109.5C8—N2—C7120.89 (17)
H1AA—C1A—H1AC109.5C8—N2—C6120.77 (17)
H1AB—C1A—H1AC109.5C7—N2—C6117.89 (17)
C8A—N2A—C7A120.78 (18)N3—C2—N1115.58 (19)
C8A—N2A—C6A121.61 (18)N3—C2—H2122.6 (9)
C7A—N2A—C6A117.57 (18)N1—C2—H2121.8 (9)
N3A—C2A—N1A115.10 (19)C2—N3—C4104.80 (16)
N3A—C2A—H2A124.1 (10)C8—C3—C4120.7 (2)
N1A—C2A—H2A120.8 (10)C8—C3—H3122.0 (10)
C2A—N3A—C4A105.09 (16)C4—C3—H3117.2 (10)
C8A—C3A—C4A121.5 (2)N3—C4—C5107.98 (15)
C8A—C3A—H3A119.8 (9)N3—C4—C3121.21 (17)
C4A—C3A—H3A118.7 (9)C5—C4—C3130.78 (17)
N3A—C4A—C5A107.95 (15)O2—N4—O1122.57 (17)
N3A—C4A—C3A122.03 (17)O2—N4—C5118.48 (17)
C5A—C4A—C3A130.00 (18)O1—N4—C5118.93 (17)
O1A—N4A—O2A121.28 (18)N4—C5—N1123.21 (17)
O1A—N4A—C5A120.07 (17)N4—C5—C4129.14 (18)
O2A—N4A—C5A118.65 (17)N1—C5—C4107.50 (16)
N4A—C5A—N1A122.98 (18)N2—C6—H6A109.5
N4A—C5A—C4A129.37 (18)N2—C6—H6B109.5
N1A—C5A—C4A107.64 (16)H6A—C6—H6B109.5
N2A—C6A—H6AA109.5N2—C6—H6C109.5
N2A—C6A—H6AB109.5H6A—C6—H6C109.5
H6AA—C6A—H6AB109.5H6B—C6—H6C109.5
N2A—C6A—H6AC109.5N2—C7—H7A109.5
H6AA—C6A—H6AC109.5N2—C7—H7B109.5
H6AB—C6A—H6AC109.5H7A—C7—H7B109.5
N2A—C7A—H7AA109.5N2—C7—H7C109.5
N2A—C7A—H7AB109.5H7A—C7—H7C109.5
H7AA—C7A—H7AB109.5H7B—C7—H7C109.5
N2A—C7A—H7AC109.5N2—C8—C3128.0 (2)
H7AA—C7A—H7AC109.5N2—C8—H8112.8 (8)
H7AB—C7A—H7AC109.5C3—C8—H8119.3 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1Ai0.954 (15)2.399 (15)3.235 (3)146 (1)
C2A—H2A···O1ii0.958 (16)2.254 (15)3.181 (3)162 (1)
C6—H6B···O1Aiii0.962.583.461 (3)153
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y1/2, z+3/2; (iii) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1Ai0.954 (15)2.399 (15)3.235 (3)146 (1)
C2A—H2A···O1ii0.958 (16)2.254 (15)3.181 (3)162 (1)
C6—H6B···O1Aiii0.962.583.461 (3)153
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y1/2, z+3/2; (iii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC8H12N4O2
Mr196.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)10.5015 (12), 23.561 (3), 7.7533 (6)
β (°) 96.604 (8)
V3)1905.6 (3)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerOxford Diffraction Xcalibur S CCD
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10647, 3875, 1523
Rint0.038
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.066, 1.00
No. of reflections3875
No. of parameters284
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.12

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Acknowledgements

We thank the Ministry of Education and Science of the Russian Federation (State task 4.1626.2014/K) for financial support

References

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