Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047939/hg2297sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047939/hg2297Isup2.hkl |
CCDC reference: 667296
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.135
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N3 - N4 .. 5.12 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Etter (1990); Kagabu (1999); Yamamoto (1996); Yamamoto & Casida (1999).
A suspension of 3-choro-1-phenylpropan-1-one (1.68 g, 10 mmol), nitroimino imidazolidine (1.31 g, 10 mmol) and potassium carbonate (1.38 g, 10 mmol) in 25 ml of methyl cyanide was heated to reflux for 30 min. The reaction was quenched with water and extracted with methylene chloride. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was purified by silica gel column chromatography to give the target compound. The crystal was grown by slow evaporation of an ethanol solution at room temperature. Anal. Calcd for C12H14N4O3: C, 55.90; H, 5.63; N, 8.69. Found: C, 55.67; H, 5.64; N, 8.66. 1H NMR (CDCl3): 3.372 (b, 2H, CH2), 3.775 (s, 6H, –NCH2N–), 7.465–7.551 (m, 2H, Ar—H), 7.623–7.579 (m, 1H, Ar—H), 7.660 (dd, 2H, Ar—H), 8.020 (s, 1H, NH).
Although all H atoms were visible in difference maps, they were placed in geometrically calculated positions, with C—H distances in the range 0.93–0.97 Å and N—H distances of 0.86 Å, and included in the final refinement in the riding model approximation,with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H atoms.
Neonicotinoids (Yamamoto, 1996) represent a novel and distinct chemical class of insecticides with remarkable chemical and biological properties (Yamamoto Casida, 1999), which hold low degree of toxicity to mammals and aquatic life, and stability in the fields. Neonicotinoids act at the acetylcholine binding site of the nicotinic acetylcholine receptor (nAChR) of insects and the nitroimino imidazolidine is an important pharmcophore. Kagabu proposed that the nitrogen atom at the 1-position of the imidazolidine ring and one of the oxygen atoms of the nitro group play an important role in the interaction with the binding sites on nAChR (Kagabu, 1999).
The molecular structure of (I) (Fig. 1) contains no crystallographically imposed symmetry. The imidazole and benzene rings in each of the ligands are not coplanar, the dihedral angle formed by the least-squares planes of the phenyl and imidazole rings being equal to 76.55 (7)°. The dihedral angles between the mean plane of the imidazole ring and the plane of the N4/O2/O3 group are 4.67 (15)°. Selected bond lengths and angles are listed in Table 1.
Analysis of the crystal packing of (I) shows the existence of three N—H···O (two intermolecular and one intramolecular) interactions between the nitrite O atoms of the L ligand and the imidazole N atom, resulting in a one-dimensional chain along with [001] direction, as shown in Fig. 2. In this 1-D chain, a hydrogen-bonded ring, N = R2(3), is generated (Etter, 1990), which comprises one imidazole N2 atom and two O atoms of the nitrite group (O2 and O3). Furthermore, this 1-D chains are extended into 2-D supramolecular sheet via C(9)—H(B)···O(2) hydrogen bonds in bc plane [Symmetry code: x, 3/2 - y, 1/2 + z], as shown in Fig. 3. A significant intramolecular C(9)—H(9 A)···N(3) interaction is also observed, which contributes strongly to the stability of the structure. All relevant hydrogen-bonding geometries are listed in Table 2.
For related literature, see: Etter (1990); Kagabu (1999); Yamamoto (1996); Yamamoto & Casida (1999).
Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C12H14N4O3 | F(000) = 552 |
Mr = 262.27 | Dx = 1.383 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1967 reflections |
a = 15.346 (4) Å | θ = 2.7–26.2° |
b = 6.0908 (15) Å | µ = 0.10 mm−1 |
c = 13.784 (3) Å | T = 294 K |
β = 102.098 (4)° | Block, colourless |
V = 1259.8 (5) Å3 | 0.28 × 0.24 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2582 independent reflections |
Radiation source: fine-focus sealed tube | 1534 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 26.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→19 |
Tmin = 0.972, Tmax = 0.980 | k = −6→7 |
6913 measured reflections | l = −17→14 |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0576P)2 + 0.2621P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2582 reflections | Δρmax = 0.17 e Å−3 |
173 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (3) |
C12H14N4O3 | V = 1259.8 (5) Å3 |
Mr = 262.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.346 (4) Å | µ = 0.10 mm−1 |
b = 6.0908 (15) Å | T = 294 K |
c = 13.784 (3) Å | 0.28 × 0.24 × 0.20 mm |
β = 102.098 (4)° |
Bruker SMART CCD area-detector diffractometer | 2582 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1534 reflections with I > 2σ(I) |
Tmin = 0.972, Tmax = 0.980 | Rint = 0.039 |
6913 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.135 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.17 e Å−3 |
2582 reflections | Δρmin = −0.19 e Å−3 |
173 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 | ||
O1 | 0.89456 (9) | 0.4085 (3) | 0.57018 (12) | 0.0741 (5) | |
O2 | 0.62133 (12) | 0.2316 (4) | 0.85036 (15) | 0.1197 (8) | |
O3 | 0.54319 (14) | −0.0283 (4) | 0.77931 (16) | 0.1252 (8) | |
N1 | 0.68641 (11) | −0.0235 (3) | 0.57030 (13) | 0.0690 (5) | |
N2 | 0.58391 (13) | −0.2046 (4) | 0.62248 (17) | 0.0955 (7) | |
H2 | 0.5493 | −0.2437 | 0.6611 | 0.115* | |
N3 | 0.65419 (10) | 0.1137 (3) | 0.71315 (13) | 0.0668 (5) | |
N4 | 0.60406 (13) | 0.1005 (4) | 0.78249 (15) | 0.0814 (6) | |
C1 | 1.07620 (13) | 0.3262 (3) | 0.62309 (14) | 0.0575 (5) | |
H1 | 1.0577 | 0.4668 | 0.6018 | 0.069* | |
C2 | 1.16612 (14) | 0.2813 (4) | 0.65379 (16) | 0.0666 (6) | |
H2A | 1.2078 | 0.3920 | 0.6533 | 0.080* | |
C3 | 1.19427 (14) | 0.0738 (4) | 0.68500 (15) | 0.0670 (6) | |
H3 | 1.2547 | 0.0448 | 0.7069 | 0.080* | |
C4 | 1.13284 (14) | −0.0900 (4) | 0.68366 (16) | 0.0694 (6) | |
H4 | 1.1519 | −0.2313 | 0.7031 | 0.083* | |
C5 | 1.04285 (14) | −0.0474 (4) | 0.65363 (15) | 0.0613 (6) | |
H5 | 1.0018 | −0.1597 | 0.6534 | 0.074* | |
C6 | 1.01342 (12) | 0.1622 (3) | 0.62384 (12) | 0.0483 (5) | |
C7 | 0.91721 (13) | 0.2204 (3) | 0.59318 (13) | 0.0528 (5) | |
C8 | 0.84777 (12) | 0.0457 (3) | 0.59221 (14) | 0.0560 (5) | |
H8A | 0.8564 | −0.0212 | 0.6574 | 0.067* | |
H8B | 0.8550 | −0.0676 | 0.5451 | 0.067* | |
C9 | 0.75451 (12) | 0.1381 (4) | 0.56442 (15) | 0.0630 (6) | |
H9A | 0.7491 | 0.2595 | 0.6083 | 0.076* | |
H9B | 0.7446 | 0.1951 | 0.4973 | 0.076* | |
C10 | 0.66626 (17) | −0.2033 (5) | 0.5001 (2) | 0.0954 (9) | |
H10A | 0.7167 | −0.3017 | 0.5055 | 0.114* | |
H10B | 0.6496 | −0.1494 | 0.4326 | 0.114* | |
C11 | 0.58803 (18) | −0.3171 (5) | 0.5314 (2) | 0.1044 (10) | |
H11A | 0.5334 | −0.2981 | 0.4821 | 0.125* | |
H11B | 0.5994 | −0.4727 | 0.5427 | 0.125* | |
C12 | 0.63860 (12) | −0.0357 (4) | 0.64033 (16) | 0.0596 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0635 (9) | 0.0647 (10) | 0.0971 (12) | −0.0063 (8) | 0.0236 (8) | 0.0197 (8) |
O2 | 0.0866 (13) | 0.189 (2) | 0.0880 (13) | −0.0068 (14) | 0.0296 (10) | −0.0507 (15) |
O3 | 0.1108 (15) | 0.163 (2) | 0.1241 (17) | −0.0436 (16) | 0.0761 (13) | −0.0316 (15) |
N1 | 0.0608 (10) | 0.0798 (13) | 0.0744 (12) | −0.0253 (9) | 0.0326 (9) | −0.0172 (10) |
N2 | 0.0827 (14) | 0.1091 (17) | 0.1117 (17) | −0.0450 (13) | 0.0591 (12) | −0.0252 (14) |
N3 | 0.0461 (9) | 0.0920 (14) | 0.0656 (11) | −0.0005 (9) | 0.0192 (8) | −0.0066 (10) |
N4 | 0.0522 (11) | 0.1243 (19) | 0.0696 (13) | 0.0040 (12) | 0.0174 (9) | −0.0096 (13) |
C1 | 0.0618 (12) | 0.0540 (12) | 0.0613 (12) | −0.0126 (10) | 0.0236 (10) | −0.0065 (9) |
C2 | 0.0551 (13) | 0.0727 (15) | 0.0761 (15) | −0.0174 (11) | 0.0232 (11) | −0.0169 (12) |
C3 | 0.0563 (12) | 0.0864 (17) | 0.0583 (13) | 0.0008 (12) | 0.0119 (10) | −0.0079 (12) |
C4 | 0.0686 (14) | 0.0687 (14) | 0.0697 (14) | 0.0024 (12) | 0.0117 (11) | 0.0087 (11) |
C5 | 0.0660 (13) | 0.0586 (13) | 0.0601 (12) | −0.0130 (10) | 0.0148 (10) | 0.0075 (10) |
C6 | 0.0539 (11) | 0.0547 (12) | 0.0395 (10) | −0.0108 (9) | 0.0171 (8) | −0.0027 (8) |
C7 | 0.0624 (12) | 0.0554 (13) | 0.0448 (11) | −0.0102 (10) | 0.0207 (9) | 0.0042 (9) |
C8 | 0.0558 (11) | 0.0613 (13) | 0.0538 (11) | −0.0144 (10) | 0.0178 (9) | −0.0012 (9) |
C9 | 0.0553 (12) | 0.0714 (15) | 0.0659 (13) | −0.0175 (10) | 0.0210 (10) | −0.0018 (11) |
C10 | 0.0881 (17) | 0.105 (2) | 0.107 (2) | −0.0444 (16) | 0.0515 (15) | −0.0386 (17) |
C11 | 0.0877 (18) | 0.113 (2) | 0.128 (2) | −0.0473 (17) | 0.0580 (17) | −0.0403 (19) |
C12 | 0.0395 (10) | 0.0732 (14) | 0.0682 (13) | −0.00 | 0.0164 (9) | 0.0008 (11) |
O1—C7 | 1.220 (2) | C3—H3 | 0.9300 |
O2—N4 | 1.216 (3) | C4—C5 | 1.381 (3) |
O3—N4 | 1.214 (3) | C4—H4 | 0.9300 |
N1—C12 | 1.332 (2) | C5—C6 | 1.387 (3) |
N1—C9 | 1.450 (2) | C5—H5 | 0.9300 |
N1—C10 | 1.451 (3) | C6—C7 | 1.491 (3) |
N2—C12 | 1.318 (3) | C7—C8 | 1.504 (3) |
N2—C11 | 1.443 (3) | C8—C9 | 1.511 (3) |
N2—H2 | 0.8600 | C8—H8A | 0.9700 |
N3—C12 | 1.338 (3) | C8—H8B | 0.9700 |
N3—N4 | 1.349 (2) | C9—H9A | 0.9700 |
C1—C2 | 1.383 (3) | C9—H9B | 0.9700 |
C1—C6 | 1.390 (2) | C10—C11 | 1.525 (3) |
C1—H1 | 0.9300 | C10—H10A | 0.9700 |
C2—C3 | 1.375 (3) | C10—H10B | 0.9700 |
C2—H2A | 0.9300 | C11—H11A | 0.9700 |
C3—C4 | 1.370 (3) | C11—H11B | 0.9700 |
C12—N1—C9 | 126.26 (18) | O1—C7—C8 | 119.96 (18) |
C12—N1—C10 | 111.61 (17) | C6—C7—C8 | 119.49 (17) |
C9—N1—C10 | 122.04 (16) | C7—C8—C9 | 111.77 (17) |
C12—N2—C11 | 113.02 (18) | C7—C8—H8A | 109.3 |
C12—N2—H2 | 123.5 | C9—C8—H8A | 109.3 |
C11—N2—H2 | 123.5 | C7—C8—H8B | 109.3 |
C12—N3—N4 | 116.87 (19) | C9—C8—H8B | 109.3 |
O3—N4—O2 | 119.6 (2) | H8A—C8—H8B | 107.9 |
O3—N4—N3 | 124.2 (2) | N1—C9—C8 | 112.88 (18) |
O2—N4—N3 | 116.2 (2) | N1—C9—H9A | 109.0 |
C2—C1—C6 | 120.3 (2) | C8—C9—H9A | 109.0 |
C2—C1—H1 | 119.9 | N1—C9—H9B | 109.0 |
C6—C1—H1 | 119.9 | C8—C9—H9B | 109.0 |
C3—C2—C1 | 120.4 (2) | H9A—C9—H9B | 107.8 |
C3—C2—H2A | 119.8 | N1—C10—C11 | 103.03 (19) |
C1—C2—H2A | 119.8 | N1—C10—H10A | 111.2 |
C4—C3—C2 | 119.7 (2) | C11—C10—H10A | 111.2 |
C4—C3—H3 | 120.2 | N1—C10—H10B | 111.2 |
C2—C3—H3 | 120.2 | C11—C10—H10B | 111.2 |
C3—C4—C5 | 120.6 (2) | H10A—C10—H10B | 109.1 |
C3—C4—H4 | 119.7 | N2—C11—C10 | 102.15 (19) |
C5—C4—H4 | 119.7 | N2—C11—H11A | 111.3 |
C4—C5—C6 | 120.34 (19) | C10—C11—H11A | 111.3 |
C4—C5—H5 | 119.8 | N2—C11—H11B | 111.3 |
C6—C5—H5 | 119.8 | C10—C11—H11B | 111.3 |
C5—C6—C1 | 118.72 (19) | H11A—C11—H11B | 109.2 |
C5—C6—C7 | 122.99 (17) | N2—C12—N1 | 109.5 (2) |
C1—C6—C7 | 118.29 (18) | N2—C12—N3 | 132.64 (19) |
O1—C7—C6 | 120.55 (17) | N1—C12—N3 | 117.82 (18) |
C12—N3—N4—O3 | −4.6 (3) | C12—N1—C9—C8 | 105.8 (2) |
C12—N3—N4—O2 | 177.2 (2) | C10—N1—C9—C8 | −70.6 (3) |
C6—C1—C2—C3 | 0.2 (3) | C7—C8—C9—N1 | −175.57 (16) |
C1—C2—C3—C4 | 1.3 (3) | C12—N1—C10—C11 | 6.7 (3) |
C2—C3—C4—C5 | −1.6 (3) | C9—N1—C10—C11 | −176.4 (2) |
C3—C4—C5—C6 | 0.4 (3) | C12—N2—C11—C10 | 7.1 (3) |
C4—C5—C6—C1 | 1.2 (3) | N1—C10—C11—N2 | −7.8 (3) |
C4—C5—C6—C7 | −178.32 (17) | C11—N2—C12—N1 | −3.2 (3) |
C2—C1—C6—C5 | −1.5 (3) | C11—N2—C12—N3 | 178.0 (2) |
C2—C1—C6—C7 | 178.05 (16) | C9—N1—C12—N2 | −179.2 (2) |
C5—C6—C7—O1 | 177.96 (18) | C10—N1—C12—N2 | −2.6 (3) |
C1—C6—C7—O1 | −1.6 (3) | C9—N1—C12—N3 | −0.3 (3) |
C5—C6—C7—C8 | −1.1 (3) | C10—N1—C12—N3 | 176.4 (2) |
C1—C6—C7—C8 | 179.35 (16) | N4—N3—C12—N2 | −2.3 (4) |
O1—C7—C8—C9 | −2.1 (3) | N4—N3—C12—N1 | 178.99 (19) |
C6—C7—C8—C9 | 177.01 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.60 | 3.272 (3) | 136 |
N2—H2···O3i | 0.86 | 2.49 | 3.260 (3) | 150 |
C9—H9B···O2ii | 0.97 | 2.50 | 3.314 (3) | 141 |
N2—H2···O3 | 0.86 | 2.11 | 2.605 (3) | 116 |
C9—H9A···N3 | 0.97 | 2.42 | 2.814 (2) | 104 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H14N4O3 |
Mr | 262.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 15.346 (4), 6.0908 (15), 13.784 (3) |
β (°) | 102.098 (4) |
V (Å3) | 1259.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.28 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.972, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6913, 2582, 1534 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.135, 1.00 |
No. of reflections | 2582 |
No. of parameters | 173 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.19 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.60 | 3.272 (3) | 136.4 |
N2—H2···O3i | 0.86 | 2.49 | 3.260 (3) | 150.0 |
C9—H9B···O2ii | 0.97 | 2.50 | 3.314 (3) | 140.9 |
N2—H2···O3 | 0.86 | 2.11 | 2.605 (3) | 116.0 |
C9—H9A···N3 | 0.97 | 2.42 | 2.814 (2) | 103.5 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2. |
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Neonicotinoids (Yamamoto, 1996) represent a novel and distinct chemical class of insecticides with remarkable chemical and biological properties (Yamamoto Casida, 1999), which hold low degree of toxicity to mammals and aquatic life, and stability in the fields. Neonicotinoids act at the acetylcholine binding site of the nicotinic acetylcholine receptor (nAChR) of insects and the nitroimino imidazolidine is an important pharmcophore. Kagabu proposed that the nitrogen atom at the 1-position of the imidazolidine ring and one of the oxygen atoms of the nitro group play an important role in the interaction with the binding sites on nAChR (Kagabu, 1999).
The molecular structure of (I) (Fig. 1) contains no crystallographically imposed symmetry. The imidazole and benzene rings in each of the ligands are not coplanar, the dihedral angle formed by the least-squares planes of the phenyl and imidazole rings being equal to 76.55 (7)°. The dihedral angles between the mean plane of the imidazole ring and the plane of the N4/O2/O3 group are 4.67 (15)°. Selected bond lengths and angles are listed in Table 1.
Analysis of the crystal packing of (I) shows the existence of three N—H···O (two intermolecular and one intramolecular) interactions between the nitrite O atoms of the L ligand and the imidazole N atom, resulting in a one-dimensional chain along with [001] direction, as shown in Fig. 2. In this 1-D chain, a hydrogen-bonded ring, N = R2(3), is generated (Etter, 1990), which comprises one imidazole N2 atom and two O atoms of the nitrite group (O2 and O3). Furthermore, this 1-D chains are extended into 2-D supramolecular sheet via C(9)—H(B)···O(2) hydrogen bonds in bc plane [Symmetry code: x, 3/2 - y, 1/2 + z], as shown in Fig. 3. A significant intramolecular C(9)—H(9 A)···N(3) interaction is also observed, which contributes strongly to the stability of the structure. All relevant hydrogen-bonding geometries are listed in Table 2.