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In the title crystal structure, 2C5H12N+·C6Cl2O42−, chloranilate and piperidinium ions are connected by bifurcated N—H...O hydrogen bonds, giving a centrosymmetric chloranirate–piperidinium 1:2 unit. The 1:2 units are connected to each other by N—H...O hydrogen bonds, forming a mol­ecular ladder. There is a centre of symmetry at the centre of the anion ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013080/lh2042sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013080/lh2042Isup2.hkl
Contains datablock I

CCDC reference: 608450

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.033
  • wR factor = 0.083
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.781 0.968 Tmin(prime) and Tmax expected: 0.889 0.968 RR(prime) = 0.878 Please check that your absorption correction is appropriate. PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1 -C3_a 1.45 Ang. PLAT335_ALERT_2_C Large Benzene C-C Range C1 -C3_a 0.16 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C3_a ... 1.54 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C5 H12 N
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 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 2 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: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); 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: CrystalStructure.

Bis(piperidinium) chloranilate top
Crystal data top
2C5H12N+·C6Cl2O42Z = 1
Mr = 379.28F(000) = 200.00
Triclinic, P1Dx = 1.506 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 5.1239 (3) ÅCell parameters from 3435 reflections
b = 8.7058 (7) Åθ = 4.0–27.1°
c = 10.4508 (7) ŵ = 0.41 mm1
α = 114.412 (3)°T = 100 K
β = 95.561 (2)°Prism, dark red
γ = 95.070 (3)°0.28 × 0.15 × 0.08 mm
V = 418.25 (5) Å3
Data collection top
Rigaku R-AXIS RAPID II
diffractometer
1534 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.045
ω scansθmax = 27.1°, θmin = 4.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 66
Tmin = 0.781, Tmax = 0.968k = 1111
4040 measured reflectionsl = 1313
1838 independent reflections
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083All H-atom parameters refined
S = 1.08 w = 1/[σ2(Fo2) + (0.0364P)2 + 0.1379P]
where P = (Fo2 + 2Fc2)/3
1838 reflections(Δ/σ)max = 0.001
158 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.38 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
Cl10.96700 (7)0.57847 (5)0.75158 (4)0.01542 (13)
O10.7985 (2)0.25722 (14)0.48983 (13)0.0164 (3)
O20.5894 (2)0.81395 (14)0.72451 (12)0.0145 (3)
N10.8960 (3)0.01402 (17)0.22845 (15)0.0124 (3)
C10.6672 (3)0.37303 (19)0.49911 (17)0.0112 (3)
C20.7079 (3)0.5373 (2)0.61515 (17)0.0122 (3)
C30.5576 (3)0.6656 (2)0.62425 (17)0.0123 (3)
C40.9625 (3)0.0916 (2)0.30577 (18)0.0146 (3)
C50.7119 (3)0.1972 (2)0.30728 (19)0.0152 (3)
C60.5820 (3)0.3121 (2)0.15509 (19)0.0165 (4)
C70.5266 (3)0.2076 (2)0.07122 (18)0.0154 (4)
C80.7743 (3)0.0928 (2)0.07768 (18)0.0135 (3)
H10.785 (4)0.081 (3)0.274 (2)0.027 (6)*
H21.036 (4)0.079 (3)0.234 (2)0.016 (5)*
H31.051 (4)0.015 (3)0.397 (2)0.017 (5)*
H41.093 (4)0.167 (3)0.255 (2)0.018 (5)*
H50.587 (4)0.120 (3)0.359 (2)0.017 (5)*
H60.752 (4)0.265 (3)0.357 (2)0.025 (5)*
H70.413 (4)0.377 (3)0.153 (2)0.027 (6)*
H80.704 (4)0.394 (3)0.108 (2)0.025 (5)*
H90.391 (4)0.135 (3)0.112 (2)0.015 (5)*
H100.465 (4)0.278 (2)0.027 (2)0.009 (4)*
H110.737 (4)0.015 (2)0.036 (2)0.010 (4)*
H120.913 (4)0.162 (3)0.032 (2)0.017 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0148 (2)0.0141 (2)0.0141 (2)0.00190 (14)0.00284 (15)0.00393 (15)
O10.0181 (6)0.0127 (5)0.0163 (6)0.0058 (5)0.0010 (5)0.0038 (5)
O20.0141 (5)0.0097 (5)0.0148 (6)0.0010 (4)0.0008 (5)0.0010 (5)
N10.0127 (6)0.0089 (6)0.0133 (7)0.0010 (6)0.0016 (6)0.0030 (5)
C10.0116 (7)0.0101 (7)0.0123 (7)0.0001 (6)0.0028 (6)0.0052 (6)
C20.0105 (7)0.0133 (7)0.0104 (7)0.0002 (6)0.0020 (6)0.0036 (6)
C30.0116 (7)0.0096 (7)0.0139 (8)0.0014 (6)0.0029 (6)0.0036 (6)
C40.0146 (8)0.0159 (8)0.0121 (8)0.0015 (6)0.0012 (6)0.0057 (6)
C50.0161 (8)0.0152 (8)0.0165 (8)0.0022 (6)0.0017 (7)0.0090 (7)
C60.0156 (8)0.0125 (7)0.0197 (8)0.0005 (7)0.0008 (7)0.0066 (7)
C70.0135 (7)0.0141 (8)0.0149 (8)0.0005 (6)0.0021 (7)0.0039 (6)
C80.0140 (8)0.0140 (8)0.0126 (8)0.0018 (6)0.0012 (6)0.0061 (6)
Geometric parameters (Å, º) top
Cl1—C21.7466 (16)C4—H41.01 (2)
O1—C11.2372 (19)C5—C61.528 (2)
O2—C31.2662 (18)C5—H51.00 (2)
N1—C41.493 (2)C5—H60.96 (2)
N1—C81.494 (2)C6—C71.527 (3)
N1—H10.88 (2)C6—H70.98 (2)
N1—H20.86 (2)C6—H80.99 (2)
C1—C21.423 (2)C7—C81.522 (2)
C1—C3i1.545 (2)C7—H90.99 (2)
C2—C31.389 (2)C7—H100.958 (19)
C3—C1i1.545 (2)C8—H110.97 (2)
C4—C51.517 (2)C8—H121.00 (2)
C4—H30.95 (2)
Cl1···N1ii3.4702 (17)O1···H12.13 (2)
Cl1···C1ii3.5045 (17)O1···H22.93 (2)
O1···N12.8045 (19)O1···H32.67 (2)
O1···C43.093 (2)O1···H3iii2.93 (2)
O1···C4iii3.239 (2)O1···H6iii2.65 (2)
O2···N1i2.9929 (19)O2···H1i2.20 (2)
O2···N1ii2.8070 (19)O2···H2ii1.98 (2)
O2···C4ii3.318 (2)O2···H9i2.59 (2)
O2···C8i3.322 (2)O2···H11vi2.95 (2)
Cl1···H2ii2.93 (3)N1···H9vii3.08 (2)
Cl1···H6iii3.04 (2)N1···H11viii3.49 (2)
Cl1···H7iv3.01 (2)C1···H12.82 (2)
Cl1···H8iii3.09 (2)C3···H1i2.86 (2)
Cl1···H10v3.05 (2)C3···H2ii2.71 (2)
Cl1···H12vi2.93 (2)C4···H3iii2.86 (2)
C4—N1—C8112.14 (13)C6—C5—H5110.0 (12)
C4—N1—H1107.4 (15)C4—C5—H6110.3 (13)
C8—N1—H1110.0 (14)C6—C5—H6109.9 (13)
C4—N1—H2108.7 (14)H5—C5—H6107.3 (18)
C8—N1—H2111.7 (14)C7—C6—C5111.01 (14)
H1—N1—H2106.7 (19)C7—C6—H7108.0 (14)
O1—C1—C2124.61 (15)C5—C6—H7111.4 (13)
O1—C1—C3i117.11 (13)C7—C6—H8109.0 (14)
C2—C1—C3i118.28 (14)C5—C6—H8108.8 (12)
C3—C2—C1123.88 (15)H7—C6—H8108.5 (18)
C3—C2—Cl1118.86 (12)C8—C7—C6111.68 (14)
C1—C2—Cl1117.24 (12)C8—C7—H9108.1 (12)
O2—C3—C2125.90 (15)C6—C7—H9109.4 (12)
O2—C3—C1i116.26 (14)C8—C7—H10106.7 (11)
C2—C3—C1i117.84 (13)C6—C7—H10112.2 (12)
N1—C4—C5109.50 (13)H9—C7—H10108.7 (15)
N1—C4—H3106.5 (13)N1—C8—C7110.41 (14)
C5—C4—H3114.4 (12)N1—C8—H11106.6 (11)
N1—C4—H4107.7 (12)C7—C8—H11112.6 (11)
C5—C4—H4111.1 (12)N1—C8—H12105.3 (11)
H3—C4—H4107.3 (16)C7—C8—H12110.9 (11)
C4—C5—C6109.84 (14)H11—C8—H12110.7 (16)
C4—C5—H5109.5 (12)
O1—C1—C2—C3179.65 (16)Cl1—C2—C3—C1i178.92 (11)
C3i—C1—C2—C30.1 (3)C8—N1—C4—C560.58 (17)
O1—C1—C2—Cl11.5 (2)N1—C4—C5—C659.06 (17)
C3i—C1—C2—Cl1178.94 (11)C4—C5—C6—C756.11 (18)
C1—C2—C3—O2179.03 (16)C5—C6—C7—C853.38 (18)
Cl1—C2—C3—O20.2 (2)C4—N1—C8—C757.27 (17)
C1—C2—C3—C1i0.1 (3)C6—C7—C8—N153.13 (18)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1; (iii) x+2, y, z+1; (iv) x+1, y, z+1; (v) x+1, y+1, z+1; (vi) x, y+1, z+1; (vii) x+1, y, z; (viii) x+2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.88 (2)2.13 (2)2.8045 (19)133.1 (17)
N1—H1···O2i0.88 (2)2.20 (2)2.9929 (19)150.7 (17)
N1—H2···O2ii0.86 (2)1.98 (2)2.8070 (19)162 (2)
C7—H9···O2i0.99 (2)2.59 (2)3.349 (2)133.5 (17)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1.
 

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