organic compounds
E)-2-(1-methyl-5-nitro-1H-imidazol-4-yl)ethenyl]amine
of dimethyl[(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
The title compound, C8H12N4O2, crystallized with two independent molecules in the 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.
Keywords: crystal structure; enamine; imidazole; layered structure; C-H⋯O hydrogen bonding.
CCDC reference: 1444628
Structure description
The title enamine was synthesized for the study of the [3 + 2] cycloaddition reactions with et al., 2012) and hydroxamoylchlorides (Bakulev et al., 2013). It crystallized with two independent molecules in the 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 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.
(BakulevIn the crystal, the two independent molecules are linked by C—H⋯O hydrogen bonds, forming zigzag chains along [10]. The chains are linked by further C—H⋯O hydrogen bonds, forming layers parallel to the ac plane; see Fig. 2 and Table 1.
Synthesis and crystallization
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 dark-red prismatic crystals.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1444628
10.1107/S2414314615024888/su5263sup1.cif
contains datablocks I, Global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314615024888/su5263Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314615024888/su5263Isup3.cml
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.
Crystal data, data collection and structure
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.The title enamine was synthesized for the study of the [3 + 2] ═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.
reactions with (Bakulev et al., 2012) and hydroxamoylchlorides (Bakulev et al., 2013). It crystallized with two independent molecules in the 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 C3In 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.
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell
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).Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
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. | |
Fig. 3. Reaction scheme. |
C8H12N4O2 | F(000) = 832 |
Mr = 196.22 | Dx = 1.368 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1523 reflections |
a = 10.5015 (12) Å | θ = 2.8–26.4° |
b = 23.561 (3) Å | µ = 0.10 mm−1 |
c = 7.7533 (6) Å | T = 295 K |
β = 96.604 (8)° | Prism, red |
V = 1905.6 (3) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 8 |
Oxford Diffraction Xcalibur S CCD diffractometer | 1523 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 26.4°, θmin = 2.8° |
ω scans | h = −13→13 |
10647 measured reflections | k = −28→29 |
3875 independent reflections | l = −9→6 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H 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 reflections | Δρmax = 0.14 e Å−3 |
284 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00217 (15) |
C8H12N4O2 | V = 1905.6 (3) Å3 |
Mr = 196.22 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.5015 (12) Å | µ = 0.10 mm−1 |
b = 23.561 (3) Å | T = 295 K |
c = 7.7533 (6) Å | 0.25 × 0.20 × 0.15 mm |
β = 96.604 (8)° |
Oxford Diffraction Xcalibur S CCD diffractometer | 1523 reflections with I > 2σ(I) |
10647 measured reflections | Rint = 0.038 |
3875 independent reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.14 e Å−3 |
3875 reflections | Δρmin = −0.12 e Å−3 |
284 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.44977 (16) | 0.40312 (6) | 0.2065 (2) | 0.0497 (5) | |
N1A | 1.04292 (17) | −0.01495 (7) | 0.7905 (2) | 0.0531 (5) | |
O1A | 0.80215 (14) | −0.03162 (6) | 0.6211 (2) | 0.0983 (6) | |
C1A | 1.02942 (19) | −0.07638 (7) | 0.7864 (2) | 0.0718 (6) | |
H1AA | 1.1008 | −0.0933 | 0.8564 | 0.108* | |
H1AB | 1.0273 | −0.0895 | 0.6689 | 0.108* | |
H1AC | 0.9512 | −0.0869 | 0.8312 | 0.108* | |
O2A | 0.78287 (14) | 0.05713 (6) | 0.56123 (18) | 0.0818 (5) | |
N2A | 1.02826 (16) | 0.23407 (8) | 0.7367 (2) | 0.0608 (5) | |
C2A | 1.1448 (2) | 0.01246 (9) | 0.8654 (3) | 0.0615 (6) | |
N3A | 1.14002 (15) | 0.06755 (7) | 0.8499 (2) | 0.0587 (5) | |
C3A | 0.9826 (2) | 0.13453 (8) | 0.7150 (3) | 0.0510 (6) | |
C4A | 1.02459 (18) | 0.07855 (7) | 0.7556 (2) | 0.0454 (5) | |
N4A | 0.84503 (18) | 0.01685 (7) | 0.6297 (2) | 0.0619 (5) | |
C5A | 0.96365 (19) | 0.02736 (8) | 0.7181 (2) | 0.0471 (5) | |
C6A | 1.12128 (19) | 0.27801 (8) | 0.7863 (3) | 0.0796 (7) | |
H6AA | 1.1992 | 0.2611 | 0.8394 | 0.119* | |
H6AB | 1.0881 | 0.3033 | 0.8672 | 0.119* | |
H6AC | 1.1384 | 0.2988 | 0.6850 | 0.119* | |
C7A | 0.9047 (2) | 0.25138 (8) | 0.6542 (3) | 0.0795 (8) | |
H7AA | 0.8388 | 0.2348 | 0.7140 | 0.119* | |
H7AB | 0.8947 | 0.2389 | 0.5355 | 0.119* | |
H7AC | 0.8981 | 0.2920 | 0.6580 | 0.119* | |
C8A | 1.0565 (2) | 0.17934 (9) | 0.7605 (3) | 0.0511 (6) | |
O1 | 0.66579 (13) | 0.42352 (6) | 0.43092 (17) | 0.0828 (5) | |
C1 | 0.46003 (19) | 0.46466 (8) | 0.2120 (2) | 0.0690 (7) | |
H1A | 0.3908 | 0.4810 | 0.1365 | 0.104* | |
H1B | 0.5402 | 0.4760 | 0.1745 | 0.104* | |
H1C | 0.4559 | 0.4776 | 0.3286 | 0.104* | |
O2 | 0.71826 (12) | 0.33445 (6) | 0.43022 (17) | 0.0716 (4) | |
N2 | 0.49194 (15) | 0.15456 (7) | 0.21675 (19) | 0.0565 (5) | |
C2 | 0.3544 (2) | 0.37399 (10) | 0.1211 (3) | 0.0557 (6) | |
N3 | 0.36672 (15) | 0.31899 (7) | 0.12659 (19) | 0.0540 (5) | |
C3 | 0.5290 (2) | 0.25429 (8) | 0.2591 (3) | 0.0490 (6) | |
C4 | 0.48305 (17) | 0.30967 (7) | 0.2234 (2) | 0.0436 (5) | |
N4 | 0.64519 (17) | 0.37394 (7) | 0.3824 (2) | 0.0553 (5) | |
C5 | 0.53483 (19) | 0.36189 (8) | 0.2743 (2) | 0.0440 (5) | |
C6 | 0.4020 (2) | 0.11081 (8) | 0.1539 (3) | 0.0760 (7) | |
H6A | 0.3369 | 0.1268 | 0.0710 | 0.114* | |
H6B | 0.3630 | 0.0952 | 0.2495 | 0.114* | |
H6C | 0.4463 | 0.0813 | 0.0995 | 0.114* | |
C7 | 0.60698 (19) | 0.13755 (8) | 0.3232 (2) | 0.0726 (7) | |
H7A | 0.6803 | 0.1529 | 0.2759 | 0.109* | |
H7B | 0.6125 | 0.0969 | 0.3254 | 0.109* | |
H7C | 0.6049 | 0.1515 | 0.4391 | 0.109* | |
C8 | 0.4624 (2) | 0.20899 (9) | 0.1940 (3) | 0.0494 (6) | |
H2 | 0.2798 (15) | 0.3923 (6) | 0.0652 (19) | 0.048 (5)* | |
H2A | 1.2150 (16) | −0.0078 (6) | 0.927 (2) | 0.064 (6)* | |
H8A | 1.1417 (15) | 0.1740 (6) | 0.8116 (19) | 0.057 (6)* | |
H3A | 0.9011 (15) | 0.1399 (6) | 0.6555 (19) | 0.054 (6)* | |
H8 | 0.3814 (15) | 0.2149 (6) | 0.1173 (19) | 0.049 (5)* | |
H3 | 0.6049 (15) | 0.2509 (6) | 0.3238 (19) | 0.053 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0538 (11) | 0.0434 (11) | 0.0506 (11) | 0.0017 (10) | 0.0003 (9) | 0.0025 (9) |
N1A | 0.0560 (12) | 0.0434 (11) | 0.0594 (12) | 0.0008 (10) | 0.0038 (10) | 0.0030 (9) |
O1A | 0.0962 (13) | 0.0684 (10) | 0.1209 (14) | −0.0340 (9) | −0.0282 (10) | 0.0003 (10) |
C1A | 0.0934 (17) | 0.0440 (14) | 0.0788 (16) | −0.0007 (12) | 0.0138 (13) | 0.0044 (13) |
O2A | 0.0665 (10) | 0.0818 (11) | 0.0895 (12) | −0.0025 (9) | −0.0231 (9) | 0.0131 (9) |
N2A | 0.0581 (13) | 0.0494 (12) | 0.0741 (13) | 0.0052 (10) | 0.0046 (11) | 0.0024 (10) |
C2A | 0.0515 (15) | 0.0555 (16) | 0.0745 (17) | 0.0045 (13) | −0.0050 (13) | 0.0077 (14) |
N3A | 0.0482 (11) | 0.0517 (11) | 0.0727 (12) | 0.0015 (9) | −0.0082 (9) | 0.0051 (10) |
C3A | 0.0460 (16) | 0.0481 (15) | 0.0568 (15) | 0.0001 (12) | −0.0038 (13) | 0.0024 (11) |
C4A | 0.0420 (13) | 0.0476 (13) | 0.0464 (13) | −0.0023 (11) | 0.0045 (11) | 0.0032 (11) |
N4A | 0.0610 (14) | 0.0622 (13) | 0.0594 (13) | −0.0089 (11) | −0.0062 (11) | 0.0008 (11) |
C5A | 0.0440 (13) | 0.0477 (14) | 0.0483 (14) | −0.0026 (12) | −0.0003 (11) | 0.0006 (11) |
C6A | 0.0816 (17) | 0.0568 (15) | 0.1014 (18) | −0.0096 (13) | 0.0145 (15) | −0.0051 (13) |
C7A | 0.0725 (18) | 0.0775 (18) | 0.0875 (17) | 0.0255 (13) | 0.0043 (15) | 0.0161 (13) |
C8A | 0.0484 (15) | 0.0473 (15) | 0.0570 (15) | 0.0094 (12) | 0.0035 (12) | 0.0023 (12) |
O1 | 0.0893 (12) | 0.0601 (9) | 0.0920 (12) | −0.0178 (8) | −0.0203 (9) | −0.0156 (9) |
C1 | 0.0809 (16) | 0.0462 (14) | 0.0779 (16) | 0.0007 (11) | 0.0001 (13) | 0.0059 (12) |
O2 | 0.0562 (9) | 0.0739 (10) | 0.0796 (10) | 0.0090 (8) | −0.0139 (8) | −0.0015 (8) |
N2 | 0.0629 (12) | 0.0424 (12) | 0.0633 (12) | 0.0028 (9) | 0.0032 (10) | 0.0003 (10) |
C2 | 0.0483 (15) | 0.0629 (16) | 0.0535 (15) | 0.0034 (13) | −0.0048 (12) | 0.0048 (13) |
N3 | 0.0531 (11) | 0.0482 (11) | 0.0583 (11) | 0.0049 (8) | −0.0036 (9) | 0.0007 (9) |
C3 | 0.0437 (15) | 0.0555 (16) | 0.0470 (14) | 0.0015 (12) | 0.0013 (12) | −0.0002 (12) |
C4 | 0.0455 (14) | 0.0485 (13) | 0.0363 (12) | 0.0022 (11) | 0.0030 (10) | 0.0028 (11) |
N4 | 0.0538 (12) | 0.0571 (13) | 0.0534 (12) | −0.0025 (10) | 0.0000 (10) | −0.0006 (10) |
C5 | 0.0425 (13) | 0.0466 (14) | 0.0413 (13) | −0.0020 (11) | −0.0014 (11) | −0.0022 (11) |
C6 | 0.0903 (18) | 0.0578 (15) | 0.0823 (16) | −0.0160 (13) | 0.0199 (15) | −0.0092 (13) |
C7 | 0.0865 (18) | 0.0634 (16) | 0.0663 (15) | 0.0184 (12) | 0.0015 (14) | 0.0055 (12) |
C8 | 0.0527 (15) | 0.0493 (15) | 0.0463 (14) | 0.0022 (12) | 0.0061 (12) | −0.0010 (11) |
N1—C2 | 1.327 (2) | C7A—H7AB | 0.9600 |
N1—C5 | 1.382 (2) | C7A—H7AC | 0.9600 |
N1—C1 | 1.4543 (19) | C8A—H8A | 0.944 (14) |
N1A—C2A | 1.325 (2) | O1—N4 | 1.2387 (17) |
N1A—C5A | 1.376 (2) | C1—H1A | 0.9600 |
N1A—C1A | 1.4544 (19) | C1—H1B | 0.9600 |
O1A—N4A | 1.2264 (17) | C1—H1C | 0.9600 |
C1A—H1AA | 0.9600 | O2—N4 | 1.2355 (17) |
C1A—H1AB | 0.9600 | N2—C8 | 1.326 (2) |
C1A—H1AC | 0.9600 | N2—C7 | 1.4393 (19) |
O2A—N4A | 1.2365 (17) | N2—C6 | 1.444 (2) |
N2A—C8A | 1.331 (2) | C2—N3 | 1.303 (2) |
N2A—C7A | 1.438 (2) | C2—H2 | 0.954 (14) |
N2A—C6A | 1.445 (2) | N3—C4 | 1.3760 (19) |
C2A—N3A | 1.304 (2) | C3—C8 | 1.342 (2) |
C2A—H2A | 0.959 (15) | C3—C4 | 1.408 (2) |
N3A—C4A | 1.3665 (19) | C3—H3 | 0.895 (14) |
C3A—C8A | 1.334 (2) | C4—C5 | 1.384 (2) |
C3A—C4A | 1.415 (2) | N4—C5 | 1.379 (2) |
C3A—H3A | 0.933 (14) | C6—H6A | 0.9600 |
C4A—C5A | 1.380 (2) | C6—H6B | 0.9600 |
N4A—C5A | 1.374 (2) | C6—H6C | 0.9600 |
C6A—H6AA | 0.9600 | C7—H7A | 0.9600 |
C6A—H6AB | 0.9600 | C7—H7B | 0.9600 |
C6A—H6AC | 0.9600 | C7—H7C | 0.9600 |
C7A—H7AA | 0.9600 | C8—H8 | 0.990 (14) |
C2—N1—C5 | 104.14 (17) | N2A—C8A—C3A | 128.1 (2) |
C2—N1—C1 | 125.41 (17) | N2A—C8A—H8A | 111.9 (9) |
C5—N1—C1 | 130.33 (17) | C3A—C8A—H8A | 120.0 (9) |
C2A—N1A—C5A | 104.22 (18) | N1—C1—H1A | 109.5 |
C2A—N1A—C1A | 124.50 (17) | N1—C1—H1B | 109.5 |
C5A—N1A—C1A | 131.23 (18) | H1A—C1—H1B | 109.5 |
N1A—C1A—H1AA | 109.5 | N1—C1—H1C | 109.5 |
N1A—C1A—H1AB | 109.5 | H1A—C1—H1C | 109.5 |
H1AA—C1A—H1AB | 109.5 | H1B—C1—H1C | 109.5 |
N1A—C1A—H1AC | 109.5 | C8—N2—C7 | 120.89 (17) |
H1AA—C1A—H1AC | 109.5 | C8—N2—C6 | 120.77 (17) |
H1AB—C1A—H1AC | 109.5 | C7—N2—C6 | 117.89 (17) |
C8A—N2A—C7A | 120.78 (18) | N3—C2—N1 | 115.58 (19) |
C8A—N2A—C6A | 121.61 (18) | N3—C2—H2 | 122.6 (9) |
C7A—N2A—C6A | 117.57 (18) | N1—C2—H2 | 121.8 (9) |
N3A—C2A—N1A | 115.10 (19) | C2—N3—C4 | 104.80 (16) |
N3A—C2A—H2A | 124.1 (10) | C8—C3—C4 | 120.7 (2) |
N1A—C2A—H2A | 120.8 (10) | C8—C3—H3 | 122.0 (10) |
C2A—N3A—C4A | 105.09 (16) | C4—C3—H3 | 117.2 (10) |
C8A—C3A—C4A | 121.5 (2) | N3—C4—C5 | 107.98 (15) |
C8A—C3A—H3A | 119.8 (9) | N3—C4—C3 | 121.21 (17) |
C4A—C3A—H3A | 118.7 (9) | C5—C4—C3 | 130.78 (17) |
N3A—C4A—C5A | 107.95 (15) | O2—N4—O1 | 122.57 (17) |
N3A—C4A—C3A | 122.03 (17) | O2—N4—C5 | 118.48 (17) |
C5A—C4A—C3A | 130.00 (18) | O1—N4—C5 | 118.93 (17) |
O1A—N4A—O2A | 121.28 (18) | N4—C5—N1 | 123.21 (17) |
O1A—N4A—C5A | 120.07 (17) | N4—C5—C4 | 129.14 (18) |
O2A—N4A—C5A | 118.65 (17) | N1—C5—C4 | 107.50 (16) |
N4A—C5A—N1A | 122.98 (18) | N2—C6—H6A | 109.5 |
N4A—C5A—C4A | 129.37 (18) | N2—C6—H6B | 109.5 |
N1A—C5A—C4A | 107.64 (16) | H6A—C6—H6B | 109.5 |
N2A—C6A—H6AA | 109.5 | N2—C6—H6C | 109.5 |
N2A—C6A—H6AB | 109.5 | H6A—C6—H6C | 109.5 |
H6AA—C6A—H6AB | 109.5 | H6B—C6—H6C | 109.5 |
N2A—C6A—H6AC | 109.5 | N2—C7—H7A | 109.5 |
H6AA—C6A—H6AC | 109.5 | N2—C7—H7B | 109.5 |
H6AB—C6A—H6AC | 109.5 | H7A—C7—H7B | 109.5 |
N2A—C7A—H7AA | 109.5 | N2—C7—H7C | 109.5 |
N2A—C7A—H7AB | 109.5 | H7A—C7—H7C | 109.5 |
H7AA—C7A—H7AB | 109.5 | H7B—C7—H7C | 109.5 |
N2A—C7A—H7AC | 109.5 | N2—C8—C3 | 128.0 (2) |
H7AA—C7A—H7AC | 109.5 | N2—C8—H8 | 112.8 (8) |
H7AB—C7A—H7AC | 109.5 | C3—C8—H8 | 119.3 (8) |
D—H···A | D—H | H···A | D···A | 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+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | 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+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+3/2; (iii) −x+1, −y, −z+1. |
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) |
V (Å3) | 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 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10647, 3875, 1523 |
Rint | 0.038 |
(sin θ/λ)max (Å−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), 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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