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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—H
O hydrogen bonds.
![...](/logos/entities/ctdot_rmgif.gif)
![...](/logos/entities/ctdot_rmgif.gif)
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
Key indicators
- Powder X-ray study
- T = 295 K
- Mean
(C-C) = 0.043 Å
- R factor = 0.000
- wR factor = 0.000
- Data-to-parameter ratio = 0.0
checkCIF/PLATON results
No syntax errors found
Alert level B POWD004_ALERT_1_B No 'Bragg' R factor has been given. Please supply a value for _refine_ls_R_factor_all [R(F)], refine_ls_R_Fsqd_factor [R(F^2)] or _refine_ls_R_I_factor [R(I)]. PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 43
Alert level C CRYSC01_ALERT_1_C The word below has not been recognised as a standard identifier. yellowish RADNW01_ALERT_1_C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54059 PLAT087_ALERT_2_C Unsatisfactory S value (Too High) .............. 2.11 PLAT430_ALERT_2_C Short Inter D...A Contact O13 .. O18B .. 2.85 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O11 .. C10A .. 2.98 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O12 .. C6A .. 2.99 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O23 .. C3B .. 2.99 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 Cl O4
Alert level G RADNT01_ALERT_1_G Extra text has been found in the _diffrn_radiation_type field. Radiation given as CuK\a~1~ Radiation identified as Cu K\a RADNW01_ALERT_1_G The radiation wavelength given implies that Cu Kalpha1 has been used. Please check that this is correct. Wavelength given = 1.54059
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
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. |
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