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The title compound, C16H12BrN2O+·ClO4-, was synthesized, and characterized by 1H NMR and X-ray diffraction techniques.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015995/ci6397sup1.cif
Contains datablocks global, 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015995/ci63972sup2.hkl
Contains datablock 2

CCDC reference: 248773

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.045
  • wR factor = 0.132
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl1 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C6 - C61 ... 1.43 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O14 .. C9 .. 3.01 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 2 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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2–4-(Bromophenyl)-8-cyano-5,7-dimethyloxazolo[3,2-a]pyridin-1-ylium perchlorate top
Crystal data top
C16H12BrN2O+·ClO4Z = 2
Mr = 427.64F(000) = 428
Triclinic, P1Dx = 1.706 Mg m3
Hall symbol: -P 1Melting point: 512 K
a = 7.150 (3) ÅCu Kα radiation, λ = 1.54180 Å
b = 7.800 (2) ÅCell parameters from 25 reflections
c = 15.481 (5) Åθ = 32–35°
α = 90.68 (2)°µ = 5.13 mm1
β = 102.62 (3)°T = 293 K
γ = 98.48 (3)°Prism, yellow
V = 832.4 (5) Å30.30 × 0.30 × 0.30 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 74.8°, θmin = 2.9°
Graphite monochromatorh = 88
non–profiled ω scansk = 99
3288 measured reflectionsl = 019
3288 independent reflections1 standard reflections every 60 min
2825 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0738P)2 + 0.5105P]
where P = (Fo2 + 2Fc2)/3
3288 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.47 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.43851 (6)0.35058 (6)0.38134 (3)0.0779 (2)
N11.3875 (4)0.8098 (3)0.19734 (15)0.0427 (5)
C21.1981 (4)0.7206 (4)0.18258 (19)0.0470 (6)
H21.11860.67990.12810.056*
C31.1534 (4)0.7050 (4)0.26195 (18)0.0448 (6)
O41.3117 (3)0.7865 (3)0.32692 (12)0.0460 (5)
C51.4492 (4)0.8481 (4)0.28505 (18)0.0433 (6)
C61.6324 (4)0.9390 (4)0.32186 (19)0.0459 (6)
C71.7526 (4)0.9918 (4)0.26404 (19)0.0464 (6)
C81.6844 (5)0.9473 (4)0.17314 (19)0.0485 (7)
H81.76540.98140.13490.058*
C91.5040 (5)0.8560 (4)0.13824 (19)0.0476 (6)
C100.9839 (4)0.6240 (4)0.29167 (19)0.0453 (6)
C110.8263 (5)0.5354 (4)0.2301 (2)0.0527 (7)
H110.83040.53020.17050.063*
C120.6650 (5)0.4559 (5)0.2566 (2)0.0592 (8)
H120.56030.39680.21520.071*
C130.6594 (5)0.4641 (4)0.3447 (2)0.0541 (7)
C140.8129 (5)0.5536 (5)0.4071 (2)0.0572 (8)
H140.80670.55980.46650.069*
C150.9741 (5)0.6330 (4)0.3805 (2)0.0527 (7)
H151.07750.69330.42210.063*
C611.6918 (5)0.9709 (4)0.4155 (2)0.0536 (7)
N611.7441 (5)0.9941 (5)0.4903 (2)0.0757 (9)
C711.9508 (5)1.0915 (5)0.2986 (2)0.0578 (8)
H71A1.94011.20660.31760.087*
H71B2.02211.09780.25270.087*
H71C2.01741.03410.34790.087*
C911.4217 (6)0.8027 (5)0.0442 (2)0.0604 (9)
H91A1.51440.84260.00960.091*
H91B1.30560.85240.02370.091*
H91C1.39140.67850.03800.091*
Cl10.16164 (11)0.25699 (10)0.07652 (5)0.0530 (2)
O110.3035 (5)0.4077 (4)0.0913 (3)0.1045 (12)
O120.0070 (5)0.2911 (6)0.1035 (2)0.1031 (11)
O130.1146 (5)0.2042 (5)0.01431 (19)0.0994 (11)
O140.2421 (6)0.1269 (4)0.1278 (2)0.1019 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0581 (3)0.0769 (3)0.1007 (4)0.00607 (19)0.0328 (2)0.0044 (2)
N10.0484 (13)0.0389 (11)0.0371 (11)0.0022 (9)0.0042 (9)0.0039 (9)
C20.0472 (16)0.0463 (15)0.0416 (13)0.0005 (12)0.0020 (12)0.0028 (11)
C30.0447 (15)0.0423 (14)0.0425 (14)0.0025 (11)0.0019 (11)0.0006 (11)
O40.0436 (11)0.0518 (11)0.0382 (9)0.0011 (8)0.0055 (8)0.0008 (8)
C50.0468 (16)0.0424 (14)0.0380 (13)0.0058 (11)0.0045 (11)0.0009 (10)
C60.0476 (16)0.0432 (14)0.0423 (13)0.0034 (12)0.0028 (11)0.0001 (11)
C70.0434 (15)0.0440 (14)0.0491 (15)0.0047 (11)0.0056 (12)0.0054 (12)
C80.0497 (17)0.0495 (15)0.0450 (14)0.0038 (12)0.0100 (12)0.0095 (12)
C90.0562 (18)0.0438 (14)0.0413 (14)0.0046 (12)0.0091 (12)0.0076 (11)
C100.0446 (16)0.0444 (14)0.0448 (14)0.0030 (11)0.0078 (12)0.0017 (11)
C110.0492 (17)0.0564 (17)0.0475 (15)0.0003 (13)0.0058 (13)0.0029 (13)
C120.0509 (18)0.0597 (19)0.0588 (18)0.0001 (14)0.0006 (14)0.0066 (15)
C130.0454 (17)0.0510 (16)0.0657 (19)0.0040 (13)0.0139 (14)0.0083 (14)
C140.058 (2)0.0640 (19)0.0482 (16)0.0032 (15)0.0122 (14)0.0048 (14)
C150.0487 (17)0.0594 (18)0.0439 (14)0.0020 (13)0.0044 (12)0.0002 (13)
C610.0436 (16)0.0645 (19)0.0471 (16)0.0004 (13)0.0038 (12)0.0029 (13)
N610.064 (2)0.104 (3)0.0506 (16)0.0007 (18)0.0041 (14)0.0134 (16)
C710.0460 (17)0.0616 (19)0.0595 (18)0.0028 (14)0.0055 (14)0.0043 (15)
C910.072 (2)0.0623 (19)0.0404 (15)0.0086 (16)0.0099 (14)0.0036 (13)
Cl10.0530 (4)0.0505 (4)0.0514 (4)0.0038 (3)0.0055 (3)0.0012 (3)
O110.099 (3)0.0692 (19)0.125 (3)0.0199 (17)0.001 (2)0.0011 (18)
O120.072 (2)0.148 (3)0.098 (2)0.035 (2)0.0259 (18)0.006 (2)
O130.089 (2)0.148 (3)0.0530 (15)0.018 (2)0.0003 (15)0.0165 (17)
O140.135 (3)0.0744 (19)0.097 (2)0.039 (2)0.010 (2)0.0204 (17)
Geometric parameters (Å, º) top
Br1—C131.895 (3)C11—C121.373 (5)
N1—C51.348 (3)C11—H110.93
N1—C91.383 (4)C12—C131.375 (5)
N1—C21.398 (4)C12—H120.93
C2—C31.338 (4)C13—C141.385 (5)
C2—H20.93C14—C151.373 (5)
C3—O41.405 (3)C14—H140.93
C3—C101.450 (4)C15—H150.93
O4—C51.328 (4)C61—N611.140 (4)
C5—C61.390 (4)C71—H71A0.96
C6—C71.396 (4)C71—H71B0.96
C6—C611.426 (4)C71—H71C0.96
C7—C81.406 (4)C91—H91A0.96
C7—C711.494 (4)C91—H91B0.96
C8—C91.370 (4)C91—H91C0.96
C8—H80.93Cl1—O141.408 (3)
C9—C911.476 (4)Cl1—O131.414 (3)
C10—C111.393 (4)Cl1—O111.415 (3)
C10—C151.394 (4)Cl1—O121.418 (3)
C5—N1—C9122.0 (3)C11—C12—C13119.5 (3)
C5—N1—C2107.8 (2)C11—C12—H12120.2
C9—N1—C2130.2 (2)C13—C12—H12120.2
C3—C2—N1106.7 (2)C12—C13—C14121.0 (3)
C3—C2—H2126.6C12—C13—Br1119.4 (3)
N1—C2—H2126.6C14—C13—Br1119.6 (3)
C2—C3—O4108.8 (3)C15—C14—C13119.4 (3)
C2—C3—C10133.9 (3)C15—C14—H14120.3
O4—C3—C10117.3 (2)C13—C14—H14120.3
C5—O4—C3106.7 (2)C14—C15—C10120.5 (3)
O4—C5—N1110.0 (2)C14—C15—H15119.7
O4—C5—C6127.7 (3)C10—C15—H15119.7
N1—C5—C6122.3 (3)N61—C61—C6178.0 (4)
C5—C6—C7117.4 (3)C7—C71—H71A109.5
C5—C6—C61119.8 (3)C7—C71—H71B109.5
C7—C6—C61122.8 (3)H71A—C71—H71B109.5
C6—C7—C8118.7 (3)C7—C71—H71C109.5
C6—C7—C71120.4 (3)H71A—C71—H71C109.5
C8—C7—C71120.9 (3)H71B—C71—H71C109.5
C9—C8—C7123.1 (3)C9—C91—H91A109.5
C9—C8—H8118.5C9—C91—H91B109.5
C7—C8—H8118.5H91A—C91—H91B109.5
C8—C9—N1116.5 (3)C9—C91—H91C109.5
C8—C9—C91126.6 (3)H91A—C91—H91C109.5
N1—C9—C91116.9 (3)H91B—C91—H91C109.5
C11—C10—C15118.9 (3)O14—CL1—O13110.2 (2)
C11—C10—C3119.4 (3)O14—CL1—O11107.2 (2)
C15—C10—C3121.7 (3)O13—CL1—O11109.8 (2)
C12—C11—C10120.6 (3)O14—CL1—O12109.8 (3)
C12—C11—H11119.7O13—CL1—O12109.9 (2)
C10—C11—H11119.7O11—CL1—O12109.9 (3)
 

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