Download citation
Download citation
link to html
In the title compound, C5H10NH2+·C6HO4Cl2, two chloranilate ions are connected by O—H...O hydrogen bonds to form a dimeric unit. The piperidinium ions are linked on both sides of the dimer via a bifurcated N—H...O hydrogen bond to afford a 2:2 complex of chloranilic acid and piperidine. The 2:2 complexes are linked together to form a hydrogen-bonded molecular tape.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023365/lh6126sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023365/lh6126Isup2.hkl
Contains datablock I

CCDC reference: 227013

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.093
  • Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT333_ALERT_2_C Large Av Benzene C-C Dist. C1 - C6 = 1.44 Ang. PLAT335_ALERT_2_C Large Benzene C-C Range C1 - C6 = 0.20 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C6 = 1.54 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1990); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR92 (Altomare, et al. 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows.

(I) top
Crystal data top
C5H12N+·C6HCl2O4F(000) = 1216.00
Mr = 294.13Dx = 1.559 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 17.263 (5) Åθ = 11.7–12.0°
b = 6.800 (4) ŵ = 0.52 mm1
c = 22.832 (8) ÅT = 299 K
β = 110.80 (2)°Prismatic, dark purple
V = 2505.5 (19) Å30.30 × 0.30 × 0.25 mm
Z = 8
Data collection top
Rigaku AFC-5R
diffractometer
2029 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 3.3°
ω–2θ scansh = 022
Absorption correction: ψ scan
(North et al., 1968)
k = 28
Tmin = 0.816, Tmax = 0.877l = 2927
3924 measured reflections3 standard reflections every 97 reflections
2866 independent reflections intensity decay: 1.1%
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)] = 0.035All H-atom parameters refined
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.031P)2 + 2.03P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.01
2866 reflectionsΔρmax = 0.31 e Å3
216 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 1.4E-3 (3)
Special details top

Experimental. The scan width was (1.68 + 0.30tanθ)° with an ω scan speed of 6° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.19360 (3)0.07182 (9)0.10353 (3)0.03969 (17)
Cl20.42847 (3)0.12311 (11)0.17429 (3)0.04382 (19)
O10.14759 (9)0.0208 (3)0.01009 (8)0.0420 (4)
O20.37363 (10)0.0034 (3)0.05712 (8)0.0394 (4)
O30.47215 (9)0.0848 (3)0.05631 (7)0.0397 (4)
O40.24660 (9)0.0672 (3)0.12676 (7)0.0437 (4)
N0.09638 (13)0.1059 (3)0.12238 (9)0.0392 (5)
C10.22073 (12)0.0047 (3)0.01936 (10)0.0289 (4)
C20.25685 (12)0.0105 (3)0.02863 (10)0.0280 (4)
C30.33890 (12)0.0152 (3)0.01421 (9)0.0273 (4)
C40.39751 (12)0.0641 (3)0.05101 (10)0.0283 (4)
C50.36400 (12)0.0800 (3)0.09781 (9)0.0289 (4)
C60.27886 (13)0.0547 (3)0.08662 (10)0.0292 (4)
C70.13646 (16)0.2011 (4)0.18518 (12)0.0409 (6)
C80.17747 (16)0.0509 (4)0.23478 (11)0.0432 (6)
C90.1196 (2)0.1136 (5)0.23617 (14)0.0576 (8)
C100.0817 (2)0.2062 (5)0.17120 (15)0.0584 (8)
C110.03792 (16)0.0553 (5)0.12241 (15)0.0534 (7)
H10.423 (2)0.009 (5)0.0424 (15)0.071 (11)*
H20.1382 (18)0.058 (4)0.1102 (13)0.056 (8)*
H30.0716 (19)0.198 (5)0.0990 (15)0.061 (9)*
H40.1757 (18)0.298 (5)0.1814 (13)0.061 (9)*
H50.0934 (17)0.267 (4)0.1938 (12)0.053 (8)*
H60.2228 (16)0.003 (4)0.2262 (12)0.047 (7)*
H70.1985 (17)0.122 (4)0.2756 (14)0.058 (8)*
H80.148 (2)0.223 (7)0.2676 (19)0.112 (14)*
H90.0776 (18)0.059 (4)0.2467 (13)0.050 (8)*
H100.127 (2)0.272 (5)0.1591 (15)0.077 (10)*
H110.0436 (18)0.291 (4)0.1683 (13)0.055 (8)*
H120.0211 (18)0.109 (5)0.0813 (15)0.064 (9)*
H130.0071 (19)0.009 (4)0.1277 (13)0.055 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0388 (3)0.0451 (3)0.0306 (3)0.0028 (3)0.0066 (2)0.0056 (2)
Cl20.0340 (3)0.0664 (5)0.0291 (3)0.0003 (3)0.0089 (2)0.0068 (3)
O10.0265 (7)0.0572 (11)0.0438 (9)0.0039 (8)0.0145 (7)0.0015 (8)
O20.0327 (9)0.0574 (11)0.0337 (8)0.0018 (8)0.0184 (7)0.0068 (8)
O30.0256 (7)0.0557 (11)0.0419 (9)0.0036 (7)0.0172 (6)0.0097 (8)
O40.0367 (8)0.0648 (12)0.0382 (8)0.0072 (8)0.0238 (7)0.0080 (8)
N0.0359 (10)0.0464 (13)0.0329 (10)0.0078 (10)0.0093 (8)0.0062 (10)
C10.0271 (10)0.0276 (11)0.0341 (11)0.0012 (9)0.0136 (8)0.0026 (9)
C20.0286 (10)0.0260 (11)0.0293 (10)0.0001 (8)0.0102 (8)0.0015 (8)
C30.0307 (10)0.0264 (11)0.0290 (10)0.0014 (8)0.0156 (8)0.0011 (8)
C40.0257 (9)0.0268 (11)0.0340 (10)0.0019 (8)0.0124 (8)0.0026 (9)
C50.0268 (9)0.0329 (12)0.0273 (10)0.0007 (9)0.0098 (8)0.0024 (9)
C60.0306 (10)0.0286 (11)0.0323 (11)0.0007 (9)0.0159 (8)0.0013 (9)
C70.0391 (12)0.0389 (15)0.0451 (13)0.0013 (11)0.0153 (11)0.0058 (11)
C80.0434 (13)0.0541 (17)0.0319 (12)0.0025 (12)0.0131 (10)0.0020 (11)
C90.075 (2)0.061 (2)0.0455 (15)0.0085 (17)0.0325 (15)0.0019 (14)
C100.0680 (19)0.0494 (19)0.0617 (18)0.0212 (16)0.0275 (16)0.0049 (15)
C110.0345 (13)0.065 (2)0.0562 (17)0.0075 (13)0.0102 (12)0.0157 (15)
Geometric parameters (Å, º) top
Cl1—C21.722 (2)C5—C61.410 (3)
Cl2—C51.730 (2)C7—C81.503 (4)
O1—C11.216 (2)C7—H40.97 (3)
O2—C31.324 (2)C7—H50.95 (3)
O2—H10.79 (3)C8—C91.508 (4)
O3—C41.259 (2)C8—H60.95 (3)
O4—C61.233 (2)C8—H71.00 (3)
N—C111.490 (4)C9—C101.528 (4)
N—C71.500 (3)C9—H81.03 (4)
N—H20.92 (3)C9—H90.92 (3)
N—H30.83 (3)C10—C111.506 (5)
C1—C21.444 (3)C10—H101.02 (3)
C1—C61.545 (3)C10—H110.86 (3)
C2—C31.347 (3)C11—H120.95 (3)
C3—C41.511 (3)C11—H130.93 (3)
C4—C51.388 (3)
O1···N3.049 (3)O4···C83.200 (4)
O1···C3i3.369 (3)O4···C73.244 (3)
O1···C4ii3.380 (3)C1···C2i3.381 (4)
O2···O3iii2.713 (3)C1···C3ii3.413 (4)
O2···Ni3.177 (3)C1···C2ii3.459 (4)
O3···Niv3.000 (3)C2···C6ii3.341 (4)
O4···N2.817 (3)C2···C2i3.549 (5)
C3—O2—H1112 (2)N—C7—H5105.9 (16)
C11—N—C7113.6 (2)C8—C7—H5111.2 (17)
C11—N—H2110.0 (18)H4—C7—H5109 (2)
C7—N—H2107.4 (18)C7—C8—C9112.4 (2)
C11—N—H3111 (2)C7—C8—H6108.2 (16)
C7—N—H3104 (2)C9—C8—H6108.6 (17)
H2—N—H3111 (3)C7—C8—H7107.1 (17)
O1—C1—C2124.0 (2)C9—C8—H7111.3 (16)
O1—C1—C6118.17 (18)H6—C8—H7109 (2)
C2—C1—C6117.83 (17)C8—C9—C10110.1 (2)
C3—C2—C1120.35 (19)C8—C9—H8113 (2)
C3—C2—Cl1121.01 (16)C10—C9—H8108 (2)
C1—C2—Cl1118.59 (15)C8—C9—H9107.3 (18)
O2—C3—C2121.35 (19)C10—C9—H9108.4 (18)
O2—C3—C4115.44 (17)H8—C9—H9110 (3)
C2—C3—C4123.21 (18)C11—C10—C9111.5 (3)
O3—C4—C5127.55 (19)C11—C10—H10109.3 (19)
O3—C4—C3115.08 (18)C9—C10—H10109.8 (19)
C5—C4—C3117.36 (17)C11—C10—H11103 (2)
C4—C5—C6122.92 (19)C9—C10—H11114 (2)
C4—C5—Cl2119.71 (15)H10—C10—H11109 (3)
C6—C5—Cl2117.32 (15)N—C11—C10109.8 (2)
O4—C6—C5125.0 (2)N—C11—H12104.6 (18)
O4—C6—C1116.65 (18)C10—C11—H12111.4 (19)
C5—C6—C1118.31 (17)N—C11—H13104.6 (18)
N—C7—C8111.1 (2)C10—C11—H13116.3 (18)
N—C7—H4107.9 (17)H12—C11—H13109 (2)
C8—C7—H4111.9 (17)
O1—C1—C2—C3178.3 (2)C3—C4—C5—Cl2176.66 (16)
C6—C1—C2—C31.1 (3)C4—C5—C6—O4179.8 (2)
O1—C1—C2—Cl11.0 (3)Cl2—C5—C6—O42.5 (3)
C6—C1—C2—Cl1178.49 (15)C4—C5—C6—C10.7 (3)
C1—C2—C3—O2178.2 (2)Cl2—C5—C6—C1176.68 (16)
Cl1—C2—C3—O20.8 (3)O1—C1—C6—O40.6 (3)
C1—C2—C3—C41.1 (3)C2—C1—C6—O4179.9 (2)
Cl1—C2—C3—C4178.45 (16)O1—C1—C6—C5178.6 (2)
O2—C3—C4—O31.3 (3)C2—C1—C6—C50.9 (3)
C2—C3—C4—O3179.4 (2)C11—N—C7—C853.6 (3)
O2—C3—C4—C5178.5 (2)N—C7—C8—C952.7 (3)
C2—C3—C4—C50.9 (3)C7—C8—C9—C1054.3 (4)
O3—C4—C5—C6179.7 (2)C8—C9—C10—C1156.3 (4)
C3—C4—C5—C60.7 (3)C7—N—C11—C1055.5 (3)
O3—C4—C5—Cl23.0 (3)C9—C10—C11—N56.5 (3)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1, y, z; (iv) x+1/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O30.80 (4)2.17 (3)2.614 (3)115 (3)
O2—H1···O3iii0.80 (4)2.05 (4)2.713 (3)140 (3)
N—H2···O10.92 (3)2.36 (3)3.049 (3)131 (2)
N—H2···O40.92 (3)1.97 (3)2.817 (3)153 (2)
N—H3···O3v0.84 (3)2.21 (3)3.000 (3)157 (3)
N—H3···O2i0.84 (3)2.56 (3)3.177 (3)131 (3)
C7—H5···Cl2v0.95 (3)2.82 (3)3.708 (4)156 (2)
C8—H6···O40.95 (3)2.49 (3)3.200 (4)132 (2)
Symmetry codes: (i) x+1/2, y1/2, z; (iii) x+1, y, z; (v) x1/2, y1/2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds