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The title compound, 4-phenyl­pyridinium-3-squarate, C15H9NO3, exhibits an inter­planar angle between the pyridinium and squarate rings of 0.6 (1)°. It displays a dipolar electronic ground-state structure, with a positively charged pyridinium fragment and a negatively charged squarate moiety. In the mol­ecule, the two aromatic rings are twisted by 31.6 (1)°. The bond lengths within the squarate system represent average values for the two possible resonance structures, with a central typical carbon­yl bond [1.203 (2) Å] flanked by two longer `semicarbon­yl' bonds of lengths 1.228 (2) and 1.221 (2) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805008457/bt6631sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805008457/bt6631Isup2.hkl
Contains datablock I

CCDC reference: 270248

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.112
  • Data-to-parameter ratio = 12.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1' - C2' ... 1.53 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1' - C4' ... 1.53 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O4' .. C2 .. 2.98 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H3 .. O4' .. 2.62 Ang.
Alert level G HYDTR01_ALERT_1_G Extra text has been found in the _refine_ls_hydrogen_treatment fi Explanatory text should be in the _publ_section_refinement field. Hydrogen treatment given as constr. Hydrogen treatment identified as constr
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: R3m/V User's Guide (Siemens, 1989); cell refinement: R3m/V User's Guide; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

4-phenylpyridinium-3-squarate top
Crystal data top
C15H9NO3F(000) = 520
Mr = 251.23Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15 reflections
a = 12.852 (3) Åθ = 7.5–15°
b = 12.924 (3) ŵ = 0.10 mm1
c = 7.236 (2) ÅT = 293 K
β = 91.49 (2)°Prism, orange-red
V = 1201.4 (5) Å30.34 × 0.26 × 0.21 mm
Z = 4
Data collection top
Siemens P4 four-circle
diffractometer
1455 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 25.0°, θmin = 3.2°
Profile fitted scansh = 1515
Absorption correction: ψ scan
(XPREP in SHELXTL-Plus; Sheldrick, 1995)
k = 151
Tmin = 0.957, Tmax = 0.983l = 18
2889 measured reflections3 standard reflections every 100 reflections
2112 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.112 w = 1/[σ2(Fo2) + (0.0532P)2 + 0.0499P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2112 reflectionsΔρmax = 0.13 e Å3
173 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.037 (6)
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
N10.94652 (11)0.86755 (11)0.27545 (19)0.0374 (4)
C20.90358 (13)0.95958 (13)0.3211 (2)0.0418 (5)
H20.93811.02080.29410.050*
C30.81038 (13)0.96316 (14)0.4061 (2)0.0431 (5)
H30.78221.02700.43700.052*
C40.75627 (13)0.87285 (14)0.4478 (2)0.0392 (4)
C50.80279 (13)0.77933 (13)0.3978 (2)0.0410 (5)
H50.76910.71730.42210.049*
C60.89689 (13)0.77760 (13)0.3140 (2)0.0404 (5)
H60.92700.71470.28320.048*
C70.65479 (14)0.87656 (14)0.5389 (3)0.0437 (5)
C80.63144 (15)0.95605 (16)0.6601 (3)0.0544 (6)
H80.68091.00670.68720.065*
C90.53512 (17)0.96036 (19)0.7405 (3)0.0660 (7)
H90.52091.01300.82370.079*
C100.46063 (17)0.8879 (2)0.6989 (3)0.0727 (8)
H100.39530.89230.75080.087*
C110.48278 (16)0.8082 (2)0.5796 (3)0.0709 (7)
H110.43250.75840.55200.085*
C120.57929 (14)0.80190 (17)0.5009 (3)0.0568 (6)
H120.59390.74730.42180.068*
C3'1.04273 (13)0.86561 (13)0.1870 (2)0.0375 (4)
C2'1.11034 (13)0.94603 (14)0.1312 (2)0.0411 (4)
O2'1.11143 (10)1.04105 (10)0.1341 (2)0.0555 (4)
C1'1.18378 (14)0.86210 (14)0.0627 (3)0.0467 (5)
O1'1.26807 (12)0.86024 (12)0.0059 (2)0.0753 (5)
C4'1.10458 (14)0.78166 (14)0.1240 (3)0.0443 (5)
O4'1.09764 (11)0.68750 (10)0.1188 (2)0.0633 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0376 (8)0.0324 (8)0.0427 (8)0.0007 (6)0.0076 (6)0.0008 (6)
C20.0434 (10)0.0307 (10)0.0517 (11)0.0013 (8)0.0089 (8)0.0000 (8)
C30.0410 (10)0.0367 (10)0.0523 (11)0.0029 (8)0.0115 (8)0.0037 (8)
C40.0353 (9)0.0431 (11)0.0392 (9)0.0003 (8)0.0036 (7)0.0014 (8)
C50.0425 (10)0.0333 (10)0.0475 (11)0.0062 (8)0.0084 (8)0.0006 (8)
C60.0429 (10)0.0309 (10)0.0478 (11)0.0007 (8)0.0076 (8)0.0013 (8)
C70.0379 (10)0.0491 (11)0.0442 (10)0.0003 (8)0.0059 (8)0.0032 (9)
C80.0492 (11)0.0609 (13)0.0538 (12)0.0042 (10)0.0116 (9)0.0029 (10)
C90.0616 (14)0.0828 (17)0.0545 (13)0.0209 (13)0.0206 (11)0.0050 (12)
C100.0424 (12)0.105 (2)0.0713 (15)0.0152 (13)0.0226 (11)0.0277 (15)
C110.0415 (12)0.0910 (18)0.0808 (17)0.0116 (12)0.0105 (11)0.0153 (14)
C120.0444 (12)0.0658 (14)0.0605 (13)0.0096 (10)0.0090 (10)0.0003 (11)
C3'0.0344 (9)0.0353 (10)0.0432 (10)0.0033 (7)0.0073 (7)0.0029 (8)
C2'0.0393 (10)0.0387 (11)0.0456 (10)0.0015 (8)0.0066 (8)0.0015 (9)
O2'0.0522 (8)0.0348 (8)0.0802 (10)0.0031 (6)0.0170 (7)0.0015 (7)
C1'0.0398 (10)0.0490 (12)0.0518 (11)0.0038 (9)0.0095 (9)0.0019 (9)
O1'0.0507 (9)0.0741 (11)0.1029 (13)0.0058 (8)0.0375 (9)0.0007 (9)
C4'0.0453 (11)0.0374 (10)0.0505 (11)0.0058 (8)0.0079 (9)0.0012 (9)
O4'0.0675 (9)0.0336 (8)0.0900 (11)0.0064 (7)0.0223 (8)0.0023 (7)
Geometric parameters (Å, º) top
N1—C21.356 (2)C8—H80.9300
N1—C61.358 (2)C9—C101.367 (3)
N1—C3'1.407 (2)C9—H90.9300
C2—C31.361 (2)C10—C111.378 (3)
C2—H20.9300C10—H100.9300
C3—C41.396 (2)C11—C121.381 (3)
C3—H30.9300C11—H110.9300
C4—C51.400 (2)C12—H120.9300
C4—C71.477 (3)C3'—C2'1.420 (2)
C5—C61.367 (2)C3'—C4'1.427 (2)
C5—H50.9300C2'—O2'1.228 (2)
C6—H60.9300C2'—C1'1.529 (2)
C7—C81.388 (3)C1'—O1'1.203 (2)
C7—C121.391 (3)C1'—C4'1.529 (3)
C8—C91.383 (3)C4'—O4'1.221 (2)
C2—N1—C6120.31 (14)C10—C9—C8120.6 (2)
C2—N1—C3'119.63 (14)C10—C9—H9119.7
C6—N1—C3'120.05 (15)C8—C9—H9119.7
N1—C2—C3120.55 (16)C9—C10—C11119.7 (2)
N1—C2—H2119.7C9—C10—H10120.2
C3—C2—H2119.7C11—C10—H10120.2
C2—C3—C4121.23 (17)C10—C11—C12120.3 (2)
C2—C3—H3119.4C10—C11—H11119.8
C4—C3—H3119.4C12—C11—H11119.8
C3—C4—C5116.58 (16)C11—C12—C7120.5 (2)
C3—C4—C7121.33 (16)C11—C12—H12119.8
C5—C4—C7122.09 (16)C7—C12—H12119.8
C6—C5—C4121.16 (16)N1—C3'—C2'131.88 (16)
C6—C5—H5119.4N1—C3'—C4'131.47 (17)
C4—C5—H5119.4C2'—C3'—C4'96.65 (14)
N1—C6—C5120.16 (16)O2'—C2'—C3'137.20 (17)
N1—C6—H6119.9O2'—C2'—C1'135.08 (17)
C5—C6—H6119.9C3'—C2'—C1'87.72 (14)
C8—C7—C12118.51 (17)O1'—C1'—C2'135.87 (19)
C8—C7—C4120.90 (17)O1'—C1'—C4'135.99 (18)
C12—C7—C4120.56 (17)C2'—C1'—C4'88.12 (14)
C9—C8—C7120.4 (2)O4'—C4'—C3'136.65 (19)
C9—C8—H8119.8O4'—C4'—C1'135.86 (18)
C7—C8—H8119.8C3'—C4'—C1'87.48 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.932.383.082 (2)132
C3—H3···O4ii0.932.623.138 (2)116
C10—H10···O1iii0.932.473.330 (3)154
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+2, y+1/2, z+1/2; (iii) x1, y, z+1.
 

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