organic compounds
The title compound, C14H12N3O2+·ClO4−, crystallizes with two cations and two anions in the asymmetric unit, Z′ = 2. All bond lengths and angles show normal values. Short intermolecular O(perchlorate)N(imidazole) contacts of 2.94 (3) and 2.95 (3) Å, respectively, indicate the principal location of positive charge near the imidazole N atom in both independent cations. The crystal packing is stabilized by weak intermolecular C—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012354/lh2329sup1.cif | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S1600536807012354/lh2329IIsup2.rtv |
CCDC reference: 643656
Computing details top
Data collection: Johannson LS18 linescanner data collection program (Reference?); cell refinement: Local program; data reduction: Local program; program(s) used to solve structure: MRIA (Zlokazov & Chernyshev, 1992); program(s) used to refine structure: MRIA; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: MRIA and SHELXL97 (Sheldrick, 1997).
1-Methyl-2-(4-nitrophenyl)imidazo[1,2-a]pyridinium perchlorate top
Crystal data top
C14H12N3O2+·ClO4− | F(000) = 2912 |
Mr = 353.72 | Dx = 1.503 Mg m−3 |
Orthorhombic, Pbca | Melting point: 472 K |
Hall symbol: -P 2ac 2ab | Cu Kα1 radiation, λ = 1.54059 Å |
a = 31.393 (18) Å | µ = 2.52 mm−1 |
b = 25.527 (17) Å | T = 295 K |
c = 7.800 (5) Å | Particle morphology: plate |
V = 6251 (7) Å3 | yellowish brown |
Z = 16 | flat sheet, 7 × 7 mm |
Data collection top
Enraf–Nonius Guinier Johannson camera FR 552 diffractometer | Specimen mounting: pressed as a thin layer in the specimen holder of the camera |
Radiation source: Fine focus X-ray tube, Nonius 3502.223 | Data collection mode: transmission |
Quartz monochromator | Scan method: Stationary detector |
Refinement top
Refinement on Inet | 220 restraints |
Least-squares matrix: full with fixed elements per cycle | 36 constraints |
Rp = 0.049 | H-atom parameters constrained |
Rwp = 0.063 | Weighting scheme based on measured s.u.'s |
Rexp = 0.030 | (Δ/σ)max = 0.023 |
7881 data points | Background function: Chebyshev polynomial up to the 5th order |
Profile function: split-type pseudo-Voigt (Toraya, 1986) | Preferred orientation correction: March–Dollase (Dollase, 1986); direction of preferred orientation 001, texture parameter r = 0.93(2) |
156 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1A | 0.6177 (6) | 0.5784 (9) | 0.905 (2) | 0.057 (3)* | |
C2A | 0.6241 (9) | 0.6247 (11) | 0.811 (3) | 0.057 (3)* | |
C3A | 0.6613 (9) | 0.6188 (12) | 0.720 (3) | 0.057 (3)* | |
H3A | 0.6736 | 0.6436 | 0.6475 | 0.05* | |
N4A | 0.6773 (8) | 0.5689 (8) | 0.755 (2) | 0.057 (3)* | |
C5A | 0.7137 (9) | 0.5444 (10) | 0.695 (4) | 0.057 (3)* | |
H5A | 0.7316 | 0.5613 | 0.6179 | 0.05* | |
C6A | 0.7231 (11) | 0.4948 (12) | 0.752 (3) | 0.057 (3)* | |
H6A | 0.7476 | 0.4781 | 0.7134 | 0.05* | |
C7A | 0.6957 (9) | 0.4688 (10) | 0.869 (3) | 0.057 (3)* | |
H7A | 0.7023 | 0.4351 | 0.9061 | 0.05* | |
C8A | 0.6591 (8) | 0.4933 (11) | 0.929 (4) | 0.057 (3)* | |
H8A | 0.6409 | 0.4764 | 1.0048 | 0.05* | |
C9A | 0.6503 (8) | 0.5443 (13) | 0.871 (3) | 0.057 (3)* | |
C10A | 0.5823 (10) | 0.5667 (10) | 1.025 (3) | 0.057 (3)* | |
H10A | 0.5631 | 0.5960 | 1.0288 | 0.05* | |
H10B | 0.5936 | 0.5604 | 1.1372 | 0.05* | |
H10C | 0.5673 | 0.5362 | 0.9861 | 0.05* | |
C11A | 0.5957 (9) | 0.6710 (12) | 0.814 (3) | 0.057 (3)* | |
C12A | 0.6137 (11) | 0.7210 (12) | 0.841 (4) | 0.057 (3)* | |
H12A | 0.6429 | 0.7245 | 0.8582 | 0.05* | |
C13A | 0.5871 (9) | 0.7657 (11) | 0.842 (3) | 0.057 (3)* | |
H13A | 0.5983 | 0.7990 | 0.8585 | 0.05* | |
C14A | 0.5442 (10) | 0.7584 (14) | 0.816 (4) | 0.057 (3)* | |
C15A | 0.5253 (8) | 0.7105 (12) | 0.785 (4) | 0.057 (3)* | |
H15A | 0.4962 | 0.7079 | 0.7629 | 0.05* | |
C16A | 0.5516 (9) | 0.6656 (10) | 0.786 (3) | 0.057 (3)* | |
H16A | 0.5398 | 0.6326 | 0.7687 | 0.05* | |
N17A | 0.5168 (7) | 0.8046 (9) | 0.813 (2) | 0.057 (3)* | |
O18A | 0.4803 (6) | 0.7993 (8) | 0.760 (3) | 0.057 (3)* | |
O19A | 0.5316 (7) | 0.8468 (7) | 0.858 (2) | 0.057 (3)* | |
Cl1 | 0.6894 (3) | 0.6246 (5) | 1.2414 (11) | 0.051 (4)* | |
O11 | 0.6450 (9) | 0.6301 (9) | 1.224 (3) | 0.112 (8)* | |
O12 | 0.6992 (9) | 0.5721 (9) | 1.283 (3) | 0.144 (9)* | |
O13 | 0.7042 (9) | 0.6576 (9) | 1.374 (3) | 0.17 (1)* | |
O14 | 0.7092 (9) | 0.6382 (9) | 1.086 (3) | 0.167 (9)* | |
N1B | 0.6421 (8) | 0.4229 (8) | 0.493 (3) | 0.042 (3)* | |
C2B | 0.6282 (9) | 0.3781 (11) | 0.579 (3) | 0.042 (3)* | |
C3B | 0.5909 (8) | 0.3909 (13) | 0.664 (3) | 0.042 (3)* | |
H3B | 0.5750 | 0.3688 | 0.7333 | 0.05* | |
N4B | 0.5815 (7) | 0.4430 (9) | 0.625 (2) | 0.042 (3)* | |
C5B | 0.5472 (9) | 0.4737 (11) | 0.674 (4) | 0.042 (3)* | |
H5B | 0.5261 | 0.4601 | 0.7453 | 0.05* | |
C6B | 0.5449 (11) | 0.5245 (12) | 0.617 (3) | 0.042 (3)* | |
H6B | 0.5219 | 0.5454 | 0.6477 | 0.05* | |
C7B | 0.5775 (10) | 0.5454 (14) | 0.510 (4) | 0.042 (3)* | |
H7B | 0.5759 | 0.5800 | 0.4739 | 0.05* | |
C8B | 0.6117 (12) | 0.5146 (13) | 0.460 (3) | 0.042 (3)* | |
H8B | 0.6330 | 0.5280 | 0.3901 | 0.05* | |
C9B | 0.6132 (9) | 0.4627 (15) | 0.519 (3) | 0.042 (3)* | |
C10B | 0.6805 (11) | 0.4292 (12) | 0.384 (3) | 0.042 (3)* | |
H10D | 0.6963 | 0.3970 | 0.3832 | 0.05* | |
H10E | 0.6980 | 0.4567 | 0.4303 | 0.05* | |
H10F | 0.6721 | 0.4380 | 0.2696 | 0.05* | |
C11B | 0.6505 (10) | 0.3269 (11) | 0.585 (4) | 0.042 (3)* | |
C12B | 0.6276 (12) | 0.2812 (12) | 0.543 (4) | 0.042 (3)* | |
H12B | 0.5992 | 0.2835 | 0.5101 | 0.05* | |
C13B | 0.6481 (9) | 0.2317 (13) | 0.551 (3) | 0.042 (3)* | |
H13B | 0.6337 | 0.2009 | 0.5241 | 0.05* | |
C14B | 0.6903 (9) | 0.2314 (13) | 0.599 (3) | 0.042 (3)* | |
C15B | 0.7142 (8) | 0.2747 (15) | 0.638 (4) | 0.042 (3)* | |
H15B | 0.7429 | 0.2718 | 0.6666 | 0.05* | |
C16B | 0.6937 (10) | 0.3242 (12) | 0.633 (4) | 0.042 (3)* | |
H16B | 0.7086 | 0.3545 | 0.6609 | 0.05* | |
N17B | 0.7116 (8) | 0.1805 (7) | 0.607 (2) | 0.042 (3)* | |
O18B | 0.7469 (7) | 0.1788 (8) | 0.6738 (19) | 0.042 (3)* | |
O19B | 0.6929 (7) | 0.1424 (9) | 0.549 (2) | 0.042 (3)* | |
Cl2 | 0.5581 (4) | 0.4009 (4) | 0.1471 (10) | 0.039 (4)* | |
O21 | 0.6030 (9) | 0.3999 (9) | 0.157 (3) | 0.104 (9)* | |
O22 | 0.5442 (9) | 0.4534 (9) | 0.144 (3) | 0.150 (8)* | |
O23 | 0.5448 (9) | 0.3754 (9) | −0.004 (3) | 0.16 (1)* | |
O24 | 0.5410 (9) | 0.3754 (9) | 0.291 (3) | 0.133 (9)* |
Geometric parameters (Å, º) top
Cl1—O11 | 1.41 (3) | C15A—C16A | 1.41 (4) |
Cl1—O12 | 1.41 (3) | C3A—H3A | 0.93 |
Cl1—O13 | 1.41 (2) | C5A—H5A | 0.93 |
Cl1—O14 | 1.41 (2) | C6A—H6A | 0.93 |
Cl2—O22 | 1.41 (3) | C7A—H7A | 0.93 |
Cl2—O23 | 1.41 (2) | C8A—H8A | 0.93 |
Cl2—O21 | 1.41 (3) | C10A—H10B | 0.96 |
Cl2—O24 | 1.40 (2) | C10A—H10A | 0.96 |
O18A—N17A | 1.23 (3) | C10A—H10C | 0.96 |
O19A—N17A | 1.22 (3) | C12A—H12A | 0.93 |
O18B—N17B | 1.23 (3) | C13A—H13A | 0.93 |
O19B—N17B | 1.22 (3) | C15A—H15A | 0.93 |
N1A—C2A | 1.41 (3) | C16A—H16A | 0.93 |
N1A—C9A | 1.37 (4) | C2B—C11B | 1.48 (4) |
N1A—C10A | 1.48 (3) | C2B—C3B | 1.38 (4) |
N4A—C3A | 1.39 (4) | C5B—C6B | 1.37 (4) |
N4A—C5A | 1.38 (4) | C6B—C7B | 1.42 (4) |
N4A—C9A | 1.39 (3) | C7B—C8B | 1.39 (5) |
N17A—C14A | 1.46 (4) | C8B—C9B | 1.40 (5) |
N1B—C2B | 1.40 (3) | C11B—C16B | 1.41 (4) |
N1B—C9B | 1.38 (4) | C11B—C12B | 1.41 (4) |
N1B—C10B | 1.48 (4) | C12B—C13B | 1.42 (5) |
N4B—C5B | 1.39 (4) | C13B—C14B | 1.38 (4) |
N4B—C3B | 1.40 (4) | C14B—C15B | 1.37 (5) |
N4B—C9B | 1.39 (3) | C15B—C16B | 1.42 (5) |
N17B—C14B | 1.46 (4) | C3B—H3B | 0.93 |
C2A—C3A | 1.37 (4) | C5B—H5B | 0.93 |
C2A—C11A | 1.48 (4) | C6B—H6B | 0.93 |
C5A—C6A | 1.37 (4) | C7B—H7B | 0.93 |
C6A—C7A | 1.42 (4) | C8B—H8B | 0.93 |
C7A—C8A | 1.39 (4) | C10B—H10E | 0.96 |
C8A—C9A | 1.41 (4) | C10B—H10F | 0.96 |
C11A—C12A | 1.41 (4) | C10B—H10D | 0.96 |
C11A—C16A | 1.41 (4) | C12B—H12B | 0.93 |
C12A—C13A | 1.41 (4) | C13B—H13B | 0.93 |
C13A—C14A | 1.37 (4) | C15B—H15B | 0.93 |
C14A—C15A | 1.38 (5) | C16B—H16B | 0.93 |
O11—Cl1—O13 | 109.7 (15) | C9A—C8A—H8A | 121 |
O11—Cl1—O14 | 109.3 (14) | H10A—C10A—H10C | 109 |
O12—Cl1—O13 | 109.2 (13) | N1A—C10A—H10A | 109 |
O12—Cl1—O14 | 109.6 (15) | H10B—C10A—H10C | 109 |
O13—Cl1—O14 | 109.6 (15) | N1A—C10A—H10B | 109 |
O11—Cl1—O12 | 109.4 (16) | N1A—C10A—H10C | 109 |
O21—Cl2—O22 | 109.1 (16) | H10A—C10A—H10B | 109 |
O21—Cl2—O23 | 109.5 (15) | C11A—C12A—H12A | 120 |
O22—Cl2—O23 | 109.5 (14) | C13A—C12A—H12A | 120 |
O22—Cl2—O24 | 109.6 (14) | C12A—C13A—H13A | 121 |
O23—Cl2—O24 | 109.9 (15) | C14A—C13A—H13A | 121 |
O21—Cl2—O24 | 109.2 (15) | C16A—C15A—H15A | 121 |
C2A—N1A—C9A | 109 (2) | C14A—C15A—H15A | 121 |
C2A—N1A—C10A | 127 (2) | C11A—C16A—H16A | 120 |
C9A—N1A—C10A | 124 (2) | C15A—C16A—H16A | 120 |
C3A—N4A—C9A | 108 (2) | N1B—C2B—C3B | 108 (2) |
C5A—N4A—C9A | 121 (2) | N1B—C2B—C11B | 126 (2) |
C3A—N4A—C5A | 130 (2) | C3B—C2B—C11B | 126 (3) |
O18A—N17A—O19A | 123 (2) | N4B—C3B—C2B | 107 (2) |
O18A—N17A—C14A | 118 (2) | N4B—C5B—C6B | 119 (3) |
O19A—N17A—C14A | 119 (2) | C5B—C6B—C7B | 120 (3) |
C9B—N1B—C10B | 122 (2) | C6B—C7B—C8B | 121 (3) |
C2B—N1B—C10B | 128 (2) | C7B—C8B—C9B | 118 (3) |
C2B—N1B—C9B | 109 (2) | N1B—C9B—N4B | 107 (3) |
C5B—N4B—C9B | 121 (2) | N4B—C9B—C8B | 121 (3) |
C3B—N4B—C5B | 130 (2) | N1B—C9B—C8B | 132 (3) |
C3B—N4B—C9B | 109 (2) | C2B—C11B—C16B | 120 (3) |
O19B—N17B—C14B | 118 (2) | C12B—C11B—C16B | 121 (3) |
O18B—N17B—O19B | 124 (2) | C2B—C11B—C12B | 119 (3) |
O18B—N17B—C14B | 118 (2) | C11B—C12B—C13B | 120 (3) |
N1A—C2A—C3A | 107 (2) | C12B—C13B—C14B | 117 (3) |
C3A—C2A—C11A | 127 (3) | N17B—C14B—C15B | 117 (2) |
N1A—C2A—C11A | 125 (2) | N17B—C14B—C13B | 117 (3) |
N4A—C3A—C2A | 108 (2) | C13B—C14B—C15B | 126 (3) |
N4A—C5A—C6A | 119 (3) | C14B—C15B—C16B | 118 (3) |
C5A—C6A—C7A | 121 (3) | C11B—C16B—C15B | 119 (3) |
C6A—C7A—C8A | 120 (3) | N4B—C3B—H3B | 126 |
C7A—C8A—C9A | 118 (2) | C2B—C3B—H3B | 126 |
N1A—C9A—N4A | 107 (2) | C6B—C5B—H5B | 120 |
N4A—C9A—C8A | 121 (2) | N4B—C5B—H5B | 120 |
N1A—C9A—C8A | 132 (2) | C5B—C6B—H6B | 120 |
C2A—C11A—C16A | 121 (3) | C7B—C6B—H6B | 120 |
C2A—C11A—C12A | 119 (3) | C8B—C7B—H7B | 120 |
C12A—C11A—C16A | 120 (3) | C6B—C7B—H7B | 120 |
C11A—C12A—C13A | 120 (3) | C7B—C8B—H8B | 121 |
C12A—C13A—C14A | 118 (3) | C9B—C8B—H8B | 121 |
N17A—C14A—C15A | 117 (3) | H10D—C10B—H10F | 110 |
N17A—C14A—C13A | 118 (3) | H10E—C10B—H10F | 110 |
C13A—C14A—C15A | 125 (3) | H10D—C10B—H10E | 109 |
C14A—C15A—C16A | 118 (2) | N1B—C10B—H10D | 109 |
C11A—C16A—C15A | 120 (2) | N1B—C10B—H10E | 109 |
N4A—C3A—H3A | 126 | N1B—C10B—H10F | 110 |
C2A—C3A—H3A | 126 | C11B—C12B—H12B | 120 |
N4A—C5A—H5A | 120 | C13B—C12B—H12B | 120 |
C6A—C5A—H5A | 120 | C12B—C13B—H13B | 121 |
C5A—C6A—H6A | 120 | C14B—C13B—H13B | 122 |
C7A—C6A—H6A | 120 | C14B—C15B—H15B | 121 |
C8A—C7A—H7A | 120 | C16B—C15B—H15B | 121 |
C6A—C7A—H7A | 120 | C15B—C16B—H16B | 120 |
C7A—C8A—H8A | 121 | C11B—C16B—H16B | 120 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3A—H3A···O13i | 0.93 | 2.37 | 3.18 (3) | 145 |
C3B—H3B···O23ii | 0.93 | 2.26 | 2.99 (3) | 135 |
C3B—H3B···O18Aiii | 0.93 | 2.48 | 3.29 (4) | 145 |
C6A—H6A···O12iv | 0.93 | 2.17 | 2.99 (4) | 146 |
C7A—H7A···O19Bv | 0.93 | 2.29 | 3.17 (3) | 157 |
C15A—H15A···O24vi | 0.93 | 2.46 | 3.08 (4) | 124 |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1; (iii) −x+1, y−1/2, −z+3/2; (iv) −x+3/2, −y+1, z−1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, −y+1, −z+1. |