Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023884/rk2016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023884/rk2016Isup2.hkl |
CCDC reference: 657731
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.123
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT480_ALERT_4_C Long H...A H-Bond Reported H14 .. N13 .. 2.75 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
This is a part of our studies of intermolecular interactions in 4-nitroimidazole derivatives that started with 1-phenyl-4-nitroimidazole (Kubicki et al., 2001, 2002). Similar packing schemes and unit-cell parameters were found in 1-phenyl- and 1-(p-methylphenyl)-2-methyl-4-nitroimidazole (Kowalski, 1995). For related literature, see: Suwiński & Szczepankiewicz (1991).
The title compound was synthesized by aromatic nucleophilic sybstitution ANRORC according to procedure described before (Suwiński & Szczepankiewicz, 1991).
Isotropic displacement parameters for hydrogen atoms were calculeted as 1.2 (1.4 for the methyl group) times the Ueq value of the appropriate carrier atom.
Almost identical crystal packing was observed in the crystal structure of 1-(4-methylphenyl)-2-methyl-4-nitroimidazole (Kowalski, 1995), which crystallizes in similar unit cell (8.259 (2) Å, 7.805 (2) Å, 16.774 (3) Å). Also, there are close analogies between the intermolecular contacts in these structures. Another similar unit cell was used to describe 1-phenyl-2-methyl-4-nitroimidazole (Kowalski, 1995). In this case, however, only the projection along b-direction might be compared to the former cases; the packing along other directions looks quite different. In this case there is less intermolecular contacts in the crystal structure. This comparison might be regarded as another argument in favour of the role played by C—H···O and C—H···N hydrogen bonds in the determination of the crystal packing.
This is a part of our studies of intermolecular interactions in 4-nitroimidazole derivatives that started with 1-phenyl-4-nitroimidazole (Kubicki et al., 2001, 2002). Similar packing schemes and unit-cell parameters were found in 1-phenyl- and 1-(p-methylphenyl)-2-methyl-4-nitroimidazole (Kowalski, 1995). For related literature, see: Suwiński & Szczepankiewicz (1991).
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Stereochemical Workstation (Siemens ,1989); software used to prepare material for publication: SHELXL97.
C9H8N4O2 | F(000) = 424 |
Mr = 204.19 | Dx = 1.524 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3725 reflections |
a = 8.1315 (12) Å | θ = 3–23° |
b = 7.3189 (10) Å | µ = 0.11 mm−1 |
c = 15.104 (3) Å | T = 291 K |
β = 98.178 (14)° | Prism, colourless |
V = 889.8 (3) Å3 | 0.5 × 0.4 × 0.1 mm |
Z = 4 |
KUMA KM4CCD four-circle diffractometer | 1892 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 29.6°, θmin = 5.1° |
ω scan | h = −9→11 |
5973 measured reflections | k = −10→9 |
2311 independent reflections | l = −19→20 |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1177P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2311 reflections | Δρmax = 0.23 e Å−3 |
139 parameters | Δρmin = −0.19 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: 0.049 (8) |
C9H8N4O2 | V = 889.8 (3) Å3 |
Mr = 204.19 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.1315 (12) Å | µ = 0.11 mm−1 |
b = 7.3189 (10) Å | T = 291 K |
c = 15.104 (3) Å | 0.5 × 0.4 × 0.1 mm |
β = 98.178 (14)° |
KUMA KM4CCD four-circle diffractometer | 1892 reflections with I > 2σ(I) |
5973 measured reflections | Rint = 0.018 |
2311 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.23 e Å−3 |
2311 reflections | Δρmin = −0.19 e Å−3 |
139 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 | 0.63363 (11) | 0.17729 (13) | 0.85813 (6) | 0.0313 (2) | |
C11 | 0.64183 (13) | 0.15842 (14) | 0.76563 (7) | 0.0312 (2) | |
C12 | 0.50520 (15) | 0.10274 (17) | 0.70904 (8) | 0.0397 (3) | |
H12 | 0.4073 | 0.0812 | 0.7325 | 0.048* | |
N13 | 0.50567 (14) | 0.07805 (17) | 0.62254 (7) | 0.0483 (3) | |
C14 | 0.64606 (18) | 0.10848 (19) | 0.59085 (8) | 0.0476 (3) | |
H14 | 0.6477 | 0.0919 | 0.5299 | 0.057* | |
C15 | 0.78857 (17) | 0.16272 (19) | 0.64222 (9) | 0.0453 (3) | |
H15 | 0.8850 | 0.1821 | 0.6170 | 0.054* | |
C16 | 0.78730 (14) | 0.18828 (17) | 0.73201 (8) | 0.0387 (3) | |
H16 | 0.8827 | 0.2249 | 0.7691 | 0.046* | |
C2 | 0.51425 (13) | 0.26370 (16) | 0.89872 (7) | 0.0337 (3) | |
C21 | 0.37448 (16) | 0.3658 (2) | 0.85117 (8) | 0.0453 (3) | |
H21A | 0.3406 | 0.4585 | 0.8898 | 0.063* | |
H21B | 0.2834 | 0.2840 | 0.8334 | 0.063* | |
H21C | 0.4076 | 0.4221 | 0.7991 | 0.063* | |
N3 | 0.54348 (11) | 0.24577 (14) | 0.98488 (6) | 0.0372 (2) | |
C4 | 0.68361 (13) | 0.14672 (16) | 0.99900 (7) | 0.0344 (3) | |
N4 | 0.75007 (12) | 0.09068 (15) | 1.08599 (7) | 0.0416 (3) | |
O41 | 0.67792 (13) | 0.13436 (17) | 1.14800 (6) | 0.0582 (3) | |
O42 | 0.87520 (12) | −0.00099 (17) | 1.09452 (7) | 0.0598 (3) | |
C5 | 0.74372 (13) | 0.10265 (15) | 0.92353 (7) | 0.0343 (3) | |
H5 | 0.8390 | 0.0362 | 0.9176 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0286 (4) | 0.0398 (5) | 0.0251 (4) | 0.0019 (3) | 0.0023 (3) | −0.0022 (3) |
C11 | 0.0336 (5) | 0.0343 (5) | 0.0262 (5) | 0.0004 (4) | 0.0059 (4) | −0.0009 (4) |
C12 | 0.0362 (6) | 0.0530 (7) | 0.0300 (5) | −0.0047 (5) | 0.0052 (4) | −0.0034 (4) |
N13 | 0.0498 (6) | 0.0659 (7) | 0.0289 (5) | −0.0043 (5) | 0.0042 (4) | −0.0064 (4) |
C14 | 0.0597 (8) | 0.0559 (8) | 0.0290 (5) | 0.0035 (6) | 0.0131 (5) | −0.0010 (5) |
C15 | 0.0469 (7) | 0.0521 (7) | 0.0413 (6) | 0.0014 (5) | 0.0213 (5) | 0.0034 (5) |
C16 | 0.0354 (6) | 0.0428 (6) | 0.0390 (6) | −0.0026 (4) | 0.0091 (4) | −0.0004 (5) |
C2 | 0.0300 (5) | 0.0433 (6) | 0.0277 (5) | 0.0026 (4) | 0.0036 (4) | −0.0024 (4) |
C21 | 0.0394 (6) | 0.0584 (8) | 0.0369 (6) | 0.0146 (5) | 0.0013 (5) | 0.0004 (5) |
N3 | 0.0331 (5) | 0.0508 (6) | 0.0274 (4) | 0.0040 (4) | 0.0037 (3) | −0.0019 (4) |
C4 | 0.0302 (5) | 0.0449 (6) | 0.0270 (5) | −0.0005 (4) | 0.0001 (4) | 0.0013 (4) |
N4 | 0.0352 (5) | 0.0567 (6) | 0.0308 (5) | −0.0026 (4) | −0.0021 (4) | 0.0058 (4) |
O41 | 0.0555 (6) | 0.0917 (8) | 0.0270 (4) | 0.0024 (5) | 0.0043 (4) | 0.0054 (4) |
O42 | 0.0460 (5) | 0.0805 (8) | 0.0496 (6) | 0.0150 (5) | −0.0043 (4) | 0.0147 (5) |
C5 | 0.0299 (5) | 0.0407 (6) | 0.0314 (5) | 0.0021 (4) | 0.0008 (4) | 0.0000 (4) |
N1—C5 | 1.3505 (14) | C16—H16 | 0.9300 |
N1—C2 | 1.3738 (13) | C2—N3 | 1.2960 (14) |
N1—C11 | 1.4149 (13) | C2—C21 | 1.4608 (16) |
C11—C12 | 1.3642 (16) | C21—H21A | 0.9600 |
C11—C16 | 1.3696 (15) | C21—H21B | 0.9600 |
C12—N13 | 1.3195 (15) | C21—H21C | 0.9600 |
C12—H12 | 0.9300 | N3—C4 | 1.3418 (14) |
N13—C14 | 1.3181 (18) | C4—C5 | 1.3419 (15) |
C14—C15 | 1.359 (2) | C4—N4 | 1.4089 (14) |
C14—H14 | 0.9300 | N4—O42 | 1.2102 (14) |
C15—C16 | 1.3707 (17) | N4—O41 | 1.2165 (14) |
C15—H15 | 0.9300 | C5—H5 | 0.9300 |
C5—N1—C2 | 107.26 (9) | N3—C2—N1 | 111.18 (10) |
C5—N1—C11 | 124.28 (9) | N3—C2—C21 | 124.35 (10) |
C2—N1—C11 | 128.40 (9) | N1—C2—C21 | 124.46 (10) |
C12—C11—C16 | 118.99 (10) | C2—C21—H21A | 109.5 |
C12—C11—N1 | 119.95 (10) | C2—C21—H21B | 109.5 |
C16—C11—N1 | 121.00 (10) | H21A—C21—H21B | 109.5 |
N13—C12—C11 | 122.99 (11) | C2—C21—H21C | 109.5 |
N13—C12—H12 | 118.5 | H21A—C21—H21C | 109.5 |
C11—C12—H12 | 118.5 | H21B—C21—H21C | 109.5 |
C14—N13—C12 | 117.46 (11) | C2—N3—C4 | 104.15 (9) |
N13—C14—C15 | 123.66 (11) | N3—C4—C5 | 113.49 (10) |
N13—C14—H14 | 118.2 | N3—C4—N4 | 120.66 (10) |
C15—C14—H14 | 118.2 | C5—C4—N4 | 125.77 (11) |
C14—C15—C16 | 118.62 (11) | O42—N4—O41 | 123.64 (11) |
C14—C15—H15 | 120.7 | O42—N4—C4 | 117.76 (11) |
C16—C15—H15 | 120.7 | O41—N4—C4 | 118.59 (11) |
C11—C16—C15 | 118.27 (11) | C4—C5—N1 | 103.91 (9) |
C11—C16—H16 | 120.9 | C4—C5—H5 | 128.0 |
C15—C16—H16 | 120.9 | N1—C5—H5 | 128.0 |
C5—N1—C11—C12 | 129.18 (12) | C5—N1—C2—C21 | 178.35 (12) |
C2—N1—C11—C12 | −47.68 (16) | C11—N1—C2—C21 | −4.36 (19) |
C5—N1—C11—C16 | −48.21 (16) | N1—C2—N3—C4 | 0.08 (13) |
C2—N1—C11—C16 | 134.93 (12) | C21—C2—N3—C4 | −178.71 (12) |
C16—C11—C12—N13 | −0.83 (19) | C2—N3—C4—C5 | 0.31 (14) |
N1—C11—C12—N13 | −178.27 (11) | C2—N3—C4—N4 | −176.59 (10) |
C11—C12—N13—C14 | 0.3 (2) | N3—C4—N4—O42 | 178.79 (11) |
C12—N13—C14—C15 | 0.2 (2) | C5—C4—N4—O42 | 2.28 (19) |
N13—C14—C15—C16 | −0.3 (2) | N3—C4—N4—O41 | −0.16 (18) |
C12—C11—C16—C15 | 0.74 (18) | C5—C4—N4—O41 | −176.67 (12) |
N1—C11—C16—C15 | 178.15 (11) | N3—C4—C5—N1 | −0.57 (13) |
C14—C15—C16—C11 | −0.23 (19) | N4—C4—C5—N1 | 176.15 (11) |
C5—N1—C2—N3 | −0.44 (13) | C2—N1—C5—C4 | 0.58 (12) |
C11—N1—C2—N3 | 176.85 (10) | C11—N1—C5—C4 | −176.84 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O41i | 0.93 | 2.57 | 3.2872 (16) | 135 |
C14—H14···N13ii | 0.93 | 2.75 | 3.5557 (17) | 145 |
C15—H15···N3iii | 0.93 | 2.58 | 3.4342 (16) | 153 |
C5—H5···O42iv | 0.93 | 2.37 | 3.2358 (16) | 155 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+2, −y, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C9H8N4O2 |
Mr | 204.19 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 291 |
a, b, c (Å) | 8.1315 (12), 7.3189 (10), 15.104 (3) |
β (°) | 98.178 (14) |
V (Å3) | 889.8 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.5 × 0.4 × 0.1 |
Data collection | |
Diffractometer | KUMA KM4CCD four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5973, 2311, 1892 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.694 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.123, 1.06 |
No. of reflections | 2311 |
No. of parameters | 139 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.19 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2002), CrysAlis CCD, CrysAlis RED (Oxford Diffraction, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), Stereochemical Workstation (Siemens ,1989), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O41i | 0.93 | 2.57 | 3.2872 (16) | 134.7 |
C14—H14···N13ii | 0.93 | 2.75 | 3.5557 (17) | 144.8 |
C15—H15···N3iii | 0.93 | 2.58 | 3.4342 (16) | 153.1 |
C5—H5···O42iv | 0.93 | 2.37 | 3.2358 (16) | 154.6 |
Symmetry codes: (i) −x+1, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) x+1/2, −y+1/2, z−1/2; (iv) −x+2, −y, −z+2. |
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Almost identical crystal packing was observed in the crystal structure of 1-(4-methylphenyl)-2-methyl-4-nitroimidazole (Kowalski, 1995), which crystallizes in similar unit cell (8.259 (2) Å, 7.805 (2) Å, 16.774 (3) Å). Also, there are close analogies between the intermolecular contacts in these structures. Another similar unit cell was used to describe 1-phenyl-2-methyl-4-nitroimidazole (Kowalski, 1995). In this case, however, only the projection along b-direction might be compared to the former cases; the packing along other directions looks quite different. In this case there is less intermolecular contacts in the crystal structure. This comparison might be regarded as another argument in favour of the role played by C—H···O and C—H···N hydrogen bonds in the determination of the crystal packing.