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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807012354/lh2329sup1.cif
Contains datablocks II, global

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S1600536807012354/lh2329IIsup2.rtv
Contains datablock II

CCDC reference: 643656

Key indicators

  • Powder X-ray study
  • T = 295 K
  • Mean [sigma](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+·ClO4F(000) = 2912
Mr = 353.72Dx = 1.503 Mg m3
Orthorhombic, PbcaMelting point: 472 K
Hall symbol: -P 2ac 2abCu Kα1 radiation, λ = 1.54059 Å
a = 31.393 (18) ŵ = 2.52 mm1
b = 25.527 (17) ÅT = 295 K
c = 7.800 (5) ÅParticle morphology: plate
V = 6251 (7) Å3yellowish brown
Z = 16flat 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 3502.223Data collection mode: transmission
Quartz monochromatorScan method: Stationary detector
Refinement top
Refinement on Inet220 restraints
Least-squares matrix: full with fixed elements per cycle36 constraints
Rp = 0.049H-atom parameters constrained
Rwp = 0.063Weighting scheme based on measured s.u.'s
Rexp = 0.030(Δ/σ)max = 0.023
7881 data pointsBackground 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
Special details top

Experimental. Specimen was rotated in its plane

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N1A0.6177 (6)0.5784 (9)0.905 (2)0.057 (3)*
C2A0.6241 (9)0.6247 (11)0.811 (3)0.057 (3)*
C3A0.6613 (9)0.6188 (12)0.720 (3)0.057 (3)*
H3A0.67360.64360.64750.05*
N4A0.6773 (8)0.5689 (8)0.755 (2)0.057 (3)*
C5A0.7137 (9)0.5444 (10)0.695 (4)0.057 (3)*
H5A0.73160.56130.61790.05*
C6A0.7231 (11)0.4948 (12)0.752 (3)0.057 (3)*
H6A0.74760.47810.71340.05*
C7A0.6957 (9)0.4688 (10)0.869 (3)0.057 (3)*
H7A0.70230.43510.90610.05*
C8A0.6591 (8)0.4933 (11)0.929 (4)0.057 (3)*
H8A0.64090.47641.00480.05*
C9A0.6503 (8)0.5443 (13)0.871 (3)0.057 (3)*
C10A0.5823 (10)0.5667 (10)1.025 (3)0.057 (3)*
H10A0.56310.59601.02880.05*
H10B0.59360.56041.13720.05*
H10C0.56730.53620.98610.05*
C11A0.5957 (9)0.6710 (12)0.814 (3)0.057 (3)*
C12A0.6137 (11)0.7210 (12)0.841 (4)0.057 (3)*
H12A0.64290.72450.85820.05*
C13A0.5871 (9)0.7657 (11)0.842 (3)0.057 (3)*
H13A0.59830.79900.85850.05*
C14A0.5442 (10)0.7584 (14)0.816 (4)0.057 (3)*
C15A0.5253 (8)0.7105 (12)0.785 (4)0.057 (3)*
H15A0.49620.70790.76290.05*
C16A0.5516 (9)0.6656 (10)0.786 (3)0.057 (3)*
H16A0.53980.63260.76870.05*
N17A0.5168 (7)0.8046 (9)0.813 (2)0.057 (3)*
O18A0.4803 (6)0.7993 (8)0.760 (3)0.057 (3)*
O19A0.5316 (7)0.8468 (7)0.858 (2)0.057 (3)*
Cl10.6894 (3)0.6246 (5)1.2414 (11)0.051 (4)*
O110.6450 (9)0.6301 (9)1.224 (3)0.112 (8)*
O120.6992 (9)0.5721 (9)1.283 (3)0.144 (9)*
O130.7042 (9)0.6576 (9)1.374 (3)0.17 (1)*
O140.7092 (9)0.6382 (9)1.086 (3)0.167 (9)*
N1B0.6421 (8)0.4229 (8)0.493 (3)0.042 (3)*
C2B0.6282 (9)0.3781 (11)0.579 (3)0.042 (3)*
C3B0.5909 (8)0.3909 (13)0.664 (3)0.042 (3)*
H3B0.57500.36880.73330.05*
N4B0.5815 (7)0.4430 (9)0.625 (2)0.042 (3)*
C5B0.5472 (9)0.4737 (11)0.674 (4)0.042 (3)*
H5B0.52610.46010.74530.05*
C6B0.5449 (11)0.5245 (12)0.617 (3)0.042 (3)*
H6B0.52190.54540.64770.05*
C7B0.5775 (10)0.5454 (14)0.510 (4)0.042 (3)*
H7B0.57590.58000.47390.05*
C8B0.6117 (12)0.5146 (13)0.460 (3)0.042 (3)*
H8B0.63300.52800.39010.05*
C9B0.6132 (9)0.4627 (15)0.519 (3)0.042 (3)*
C10B0.6805 (11)0.4292 (12)0.384 (3)0.042 (3)*
H10D0.69630.39700.38320.05*
H10E0.69800.45670.43030.05*
H10F0.67210.43800.26960.05*
C11B0.6505 (10)0.3269 (11)0.585 (4)0.042 (3)*
C12B0.6276 (12)0.2812 (12)0.543 (4)0.042 (3)*
H12B0.59920.28350.51010.05*
C13B0.6481 (9)0.2317 (13)0.551 (3)0.042 (3)*
H13B0.63370.20090.52410.05*
C14B0.6903 (9)0.2314 (13)0.599 (3)0.042 (3)*
C15B0.7142 (8)0.2747 (15)0.638 (4)0.042 (3)*
H15B0.74290.27180.66660.05*
C16B0.6937 (10)0.3242 (12)0.633 (4)0.042 (3)*
H16B0.70860.35450.66090.05*
N17B0.7116 (8)0.1805 (7)0.607 (2)0.042 (3)*
O18B0.7469 (7)0.1788 (8)0.6738 (19)0.042 (3)*
O19B0.6929 (7)0.1424 (9)0.549 (2)0.042 (3)*
Cl20.5581 (4)0.4009 (4)0.1471 (10)0.039 (4)*
O210.6030 (9)0.3999 (9)0.157 (3)0.104 (9)*
O220.5442 (9)0.4534 (9)0.144 (3)0.150 (8)*
O230.5448 (9)0.3754 (9)0.004 (3)0.16 (1)*
O240.5410 (9)0.3754 (9)0.291 (3)0.133 (9)*
Geometric parameters (Å, º) top
Cl1—O111.41 (3)C15A—C16A1.41 (4)
Cl1—O121.41 (3)C3A—H3A0.93
Cl1—O131.41 (2)C5A—H5A0.93
Cl1—O141.41 (2)C6A—H6A0.93
Cl2—O221.41 (3)C7A—H7A0.93
Cl2—O231.41 (2)C8A—H8A0.93
Cl2—O211.41 (3)C10A—H10B0.96
Cl2—O241.40 (2)C10A—H10A0.96
O18A—N17A1.23 (3)C10A—H10C0.96
O19A—N17A1.22 (3)C12A—H12A0.93
O18B—N17B1.23 (3)C13A—H13A0.93
O19B—N17B1.22 (3)C15A—H15A0.93
N1A—C2A1.41 (3)C16A—H16A0.93
N1A—C9A1.37 (4)C2B—C11B1.48 (4)
N1A—C10A1.48 (3)C2B—C3B1.38 (4)
N4A—C3A1.39 (4)C5B—C6B1.37 (4)
N4A—C5A1.38 (4)C6B—C7B1.42 (4)
N4A—C9A1.39 (3)C7B—C8B1.39 (5)
N17A—C14A1.46 (4)C8B—C9B1.40 (5)
N1B—C2B1.40 (3)C11B—C16B1.41 (4)
N1B—C9B1.38 (4)C11B—C12B1.41 (4)
N1B—C10B1.48 (4)C12B—C13B1.42 (5)
N4B—C5B1.39 (4)C13B—C14B1.38 (4)
N4B—C3B1.40 (4)C14B—C15B1.37 (5)
N4B—C9B1.39 (3)C15B—C16B1.42 (5)
N17B—C14B1.46 (4)C3B—H3B0.93
C2A—C3A1.37 (4)C5B—H5B0.93
C2A—C11A1.48 (4)C6B—H6B0.93
C5A—C6A1.37 (4)C7B—H7B0.93
C6A—C7A1.42 (4)C8B—H8B0.93
C7A—C8A1.39 (4)C10B—H10E0.96
C8A—C9A1.41 (4)C10B—H10F0.96
C11A—C12A1.41 (4)C10B—H10D0.96
C11A—C16A1.41 (4)C12B—H12B0.93
C12A—C13A1.41 (4)C13B—H13B0.93
C13A—C14A1.37 (4)C15B—H15B0.93
C14A—C15A1.38 (5)C16B—H16B0.93
O11—Cl1—O13109.7 (15)C9A—C8A—H8A121
O11—Cl1—O14109.3 (14)H10A—C10A—H10C109
O12—Cl1—O13109.2 (13)N1A—C10A—H10A109
O12—Cl1—O14109.6 (15)H10B—C10A—H10C109
O13—Cl1—O14109.6 (15)N1A—C10A—H10B109
O11—Cl1—O12109.4 (16)N1A—C10A—H10C109
O21—Cl2—O22109.1 (16)H10A—C10A—H10B109
O21—Cl2—O23109.5 (15)C11A—C12A—H12A120
O22—Cl2—O23109.5 (14)C13A—C12A—H12A120
O22—Cl2—O24109.6 (14)C12A—C13A—H13A121
O23—Cl2—O24109.9 (15)C14A—C13A—H13A121
O21—Cl2—O24109.2 (15)C16A—C15A—H15A121
C2A—N1A—C9A109 (2)C14A—C15A—H15A121
C2A—N1A—C10A127 (2)C11A—C16A—H16A120
C9A—N1A—C10A124 (2)C15A—C16A—H16A120
C3A—N4A—C9A108 (2)N1B—C2B—C3B108 (2)
C5A—N4A—C9A121 (2)N1B—C2B—C11B126 (2)
C3A—N4A—C5A130 (2)C3B—C2B—C11B126 (3)
O18A—N17A—O19A123 (2)N4B—C3B—C2B107 (2)
O18A—N17A—C14A118 (2)N4B—C5B—C6B119 (3)
O19A—N17A—C14A119 (2)C5B—C6B—C7B120 (3)
C9B—N1B—C10B122 (2)C6B—C7B—C8B121 (3)
C2B—N1B—C10B128 (2)C7B—C8B—C9B118 (3)
C2B—N1B—C9B109 (2)N1B—C9B—N4B107 (3)
C5B—N4B—C9B121 (2)N4B—C9B—C8B121 (3)
C3B—N4B—C5B130 (2)N1B—C9B—C8B132 (3)
C3B—N4B—C9B109 (2)C2B—C11B—C16B120 (3)
O19B—N17B—C14B118 (2)C12B—C11B—C16B121 (3)
O18B—N17B—O19B124 (2)C2B—C11B—C12B119 (3)
O18B—N17B—C14B118 (2)C11B—C12B—C13B120 (3)
N1A—C2A—C3A107 (2)C12B—C13B—C14B117 (3)
C3A—C2A—C11A127 (3)N17B—C14B—C15B117 (2)
N1A—C2A—C11A125 (2)N17B—C14B—C13B117 (3)
N4A—C3A—C2A108 (2)C13B—C14B—C15B126 (3)
N4A—C5A—C6A119 (3)C14B—C15B—C16B118 (3)
C5A—C6A—C7A121 (3)C11B—C16B—C15B119 (3)
C6A—C7A—C8A120 (3)N4B—C3B—H3B126
C7A—C8A—C9A118 (2)C2B—C3B—H3B126
N1A—C9A—N4A107 (2)C6B—C5B—H5B120
N4A—C9A—C8A121 (2)N4B—C5B—H5B120
N1A—C9A—C8A132 (2)C5B—C6B—H6B120
C2A—C11A—C16A121 (3)C7B—C6B—H6B120
C2A—C11A—C12A119 (3)C8B—C7B—H7B120
C12A—C11A—C16A120 (3)C6B—C7B—H7B120
C11A—C12A—C13A120 (3)C7B—C8B—H8B121
C12A—C13A—C14A118 (3)C9B—C8B—H8B121
N17A—C14A—C15A117 (3)H10D—C10B—H10F110
N17A—C14A—C13A118 (3)H10E—C10B—H10F110
C13A—C14A—C15A125 (3)H10D—C10B—H10E109
C14A—C15A—C16A118 (2)N1B—C10B—H10D109
C11A—C16A—C15A120 (2)N1B—C10B—H10E109
N4A—C3A—H3A126N1B—C10B—H10F110
C2A—C3A—H3A126C11B—C12B—H12B120
N4A—C5A—H5A120C13B—C12B—H12B120
C6A—C5A—H5A120C12B—C13B—H13B121
C5A—C6A—H6A120C14B—C13B—H13B122
C7A—C6A—H6A120C14B—C15B—H15B121
C8A—C7A—H7A120C16B—C15B—H15B121
C6A—C7A—H7A120C15B—C16B—H16B120
C7A—C8A—H8A121C11B—C16B—H16B120
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3A···O13i0.932.373.18 (3)145
C3B—H3B···O23ii0.932.262.99 (3)135
C3B—H3B···O18Aiii0.932.483.29 (4)145
C6A—H6A···O12iv0.932.172.99 (4)146
C7A—H7A···O19Bv0.932.293.17 (3)157
C15A—H15A···O24vi0.932.463.08 (4)124
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1; (iii) x+1, y1/2, z+3/2; (iv) x+3/2, y+1, z1/2; (v) x, y+1/2, z+1/2; (vi) x+1, y+1, z+1.
 

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