In the title compound, 2C
4H
10N
+·C
6Cl
2O
42−, the pyrrolidinium and chloranilate ions are connected by N—H

O hydrogen bonds and arranged in an alternating manner to give an infinite molecular tape.
Supporting information
CCDC reference: 242316
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean
(C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.159
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.10
PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C1 -C6 1.44 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range C1 -C6 0.16 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C6 ... 1.54 Ang.
PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C3 - C4 ... 1.54 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C4 H10 N
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 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
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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.
Crystal data top
2C4H10N+·C6Cl2O42− | Z = 2 |
Mr = 351.23 | F(000) = 368 |
Triclinic, P1 | Dx = 1.486 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.337 (3) Å | Cell parameters from 25 reflections |
b = 9.601 (4) Å | θ = 11.2–11.8° |
c = 9.947 (5) Å | µ = 0.43 mm−1 |
α = 68.18 (3)° | T = 300 K |
β = 84.25 (3)° | Prism, dark red |
γ = 71.52 (2)° | 0.40 × 0.20 × 0.15 mm |
V = 785.0 (6) Å3 | |
Data collection top
Rigaku AFC-5R diffractometer | 2522 reflections with I > 2σ(I) |
Radiation source: Rigaku rotating anode | Rint = 0.014 |
Graphite monochromator | θmax = 27.5°, θmin = 2.2° |
ω–2θ scans | h = −12→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→0 |
Tmin = 0.91, Tmax = 0.94 | l = −12→11 |
3821 measured reflections | 3 standard reflections every 97 reflections |
3606 independent reflections | intensity decay: 1.7% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.09P)2] where P = (Fo2 + 2Fc2)/3 |
3606 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Special details top
Experimental. The scan width was (1.57 + 0.30tanθ)° with an ω scan speed of 4° 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. 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.58538 (7) | 0.46619 (8) | −0.27994 (7) | 0.0446 (2) | |
Cl2 | 0.97853 (7) | −0.05581 (7) | 0.26667 (7) | 0.03732 (19) | |
O1 | 0.8969 (2) | 0.4251 (2) | −0.1949 (2) | 0.0411 (5) | |
O2 | 0.50354 (19) | 0.1967 (2) | −0.0502 (2) | 0.0385 (4) | |
O3 | 0.6647 (2) | −0.0101 (2) | 0.1850 (2) | 0.0467 (5) | |
O4 | 1.06977 (18) | 0.1996 (2) | 0.02585 (19) | 0.0354 (4) | |
N1 | 0.2269 (2) | 0.3741 (2) | −0.1955 (2) | 0.0303 (4) | |
N2 | 0.3348 (2) | 0.0689 (2) | 0.1923 (2) | 0.0314 (4) | |
C1 | 0.8398 (2) | 0.3259 (3) | −0.1127 (3) | 0.0276 (5) | |
C2 | 0.6923 (3) | 0.3220 (3) | −0.1289 (3) | 0.0299 (5) | |
C3 | 0.6307 (2) | 0.2088 (3) | −0.0358 (3) | 0.0276 (5) | |
C4 | 0.7248 (3) | 0.0854 (3) | 0.0992 (3) | 0.0289 (5) | |
C5 | 0.8720 (2) | 0.0892 (3) | 0.1164 (2) | 0.0263 (5) | |
C6 | 0.9374 (2) | 0.1960 (3) | 0.0178 (2) | 0.0257 (5) | |
C7 | 0.2171 (3) | 0.3986 (3) | −0.3521 (3) | 0.0406 (6) | |
C8 | 0.1290 (4) | 0.5672 (4) | −0.4214 (3) | 0.0580 (9) | |
C9 | 0.1724 (4) | 0.6469 (4) | −0.3351 (4) | 0.0655 (10) | |
C10 | 0.1888 (3) | 0.5317 (3) | −0.1819 (3) | 0.0446 (7) | |
C11 | 0.3088 (4) | 0.2129 (3) | 0.2286 (3) | 0.0491 (7) | |
C12 | 0.3053 (5) | 0.1620 (4) | 0.3887 (4) | 0.0667 (10) | |
C13 | 0.2807 (4) | 0.0022 (4) | 0.4415 (3) | 0.0545 (8) | |
C14 | 0.3588 (3) | −0.0702 (3) | 0.3314 (3) | 0.0382 (6) | |
H1 | 0.3198 | 0.3164 | −0.1607 | 0.045* | |
H2 | 0.1626 | 0.3235 | −0.1451 | 0.045* | |
H3 | 0.3169 | 0.3769 | −0.3929 | 0.061* | |
H4 | 0.1657 | 0.3309 | −0.3650 | 0.061* | |
H5 | 0.1557 | 0.6087 | −0.5221 | 0.087* | |
H6 | 0.0214 | 0.5808 | −0.4162 | 0.087* | |
H7 | 0.2668 | 0.6693 | −0.3683 | 0.098* | |
H8 | 0.0946 | 0.7448 | −0.3429 | 0.098* | |
H9 | 0.2689 | 0.5371 | −0.1306 | 0.067* | |
H10 | 0.0954 | 0.5529 | −0.1303 | 0.067* | |
H11 | 0.4155 | 0.0569 | 0.1371 | 0.047* | |
H12 | 0.2552 | 0.0780 | 0.1438 | 0.047* | |
H13 | 0.3896 | 0.2595 | 0.1914 | 0.074* | |
H14 | 0.2138 | 0.2903 | 0.1862 | 0.074* | |
H15 | 0.3999 | 0.1549 | 0.4271 | 0.100* | |
H16 | 0.2237 | 0.2358 | 0.4186 | 0.100* | |
H17 | 0.3252 | −0.0614 | 0.5374 | 0.082* | |
H18 | 0.1738 | 0.0124 | 0.4446 | 0.082* | |
H19 | 0.4655 | −0.1218 | 0.3549 | 0.057* | |
H20 | 0.3132 | −0.1459 | 0.3262 | 0.057* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0321 (3) | 0.0451 (4) | 0.0429 (4) | −0.0121 (3) | −0.0090 (3) | 0.0021 (3) |
Cl2 | 0.0291 (3) | 0.0395 (4) | 0.0350 (3) | −0.0069 (2) | −0.0059 (2) | −0.0055 (3) |
O1 | 0.0301 (9) | 0.0376 (10) | 0.0496 (11) | −0.0181 (8) | 0.0002 (8) | −0.0026 (8) |
O2 | 0.0237 (8) | 0.0473 (11) | 0.0415 (10) | −0.0170 (8) | −0.0046 (7) | −0.0062 (8) |
O3 | 0.0292 (9) | 0.0460 (11) | 0.0511 (12) | −0.0193 (8) | −0.0033 (8) | 0.0051 (9) |
O4 | 0.0220 (8) | 0.0418 (10) | 0.0406 (10) | −0.0133 (7) | −0.0042 (7) | −0.0087 (8) |
N1 | 0.0231 (9) | 0.0318 (10) | 0.0322 (10) | −0.0092 (8) | −0.0012 (8) | −0.0062 (8) |
N2 | 0.0259 (10) | 0.0367 (11) | 0.0319 (11) | −0.0103 (9) | 0.0001 (8) | −0.0119 (9) |
C1 | 0.0234 (11) | 0.0271 (11) | 0.0335 (12) | −0.0096 (9) | 0.0006 (9) | −0.0105 (10) |
C2 | 0.0206 (11) | 0.0307 (12) | 0.0340 (12) | −0.0068 (9) | −0.0039 (9) | −0.0067 (10) |
C3 | 0.0186 (10) | 0.0312 (12) | 0.0331 (12) | −0.0074 (9) | 0.0006 (9) | −0.0118 (10) |
C4 | 0.0218 (11) | 0.0307 (12) | 0.0342 (12) | −0.0098 (9) | 0.0026 (9) | −0.0109 (10) |
C5 | 0.0219 (10) | 0.0282 (11) | 0.0281 (11) | −0.0057 (9) | −0.0014 (8) | −0.0105 (9) |
C6 | 0.0194 (10) | 0.0289 (11) | 0.0324 (12) | −0.0080 (9) | 0.0019 (9) | −0.0150 (10) |
C7 | 0.0433 (15) | 0.0445 (15) | 0.0331 (13) | −0.0103 (12) | −0.0019 (11) | −0.0149 (12) |
C8 | 0.056 (2) | 0.0555 (19) | 0.0408 (17) | −0.0045 (16) | −0.0043 (14) | −0.0020 (14) |
C9 | 0.062 (2) | 0.0315 (15) | 0.089 (3) | −0.0111 (15) | −0.0076 (19) | −0.0075 (17) |
C10 | 0.0382 (15) | 0.0500 (17) | 0.0574 (18) | −0.0163 (13) | 0.0035 (13) | −0.0307 (15) |
C11 | 0.0573 (19) | 0.0373 (15) | 0.0547 (18) | −0.0114 (13) | −0.0033 (14) | −0.0200 (13) |
C12 | 0.087 (3) | 0.066 (2) | 0.054 (2) | −0.016 (2) | −0.0006 (18) | −0.0357 (18) |
C13 | 0.0556 (19) | 0.073 (2) | 0.0380 (15) | −0.0246 (17) | 0.0067 (13) | −0.0199 (15) |
C14 | 0.0343 (13) | 0.0342 (13) | 0.0387 (14) | −0.0100 (11) | −0.0019 (11) | −0.0045 (11) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.746 (3) | C7—H3 | 0.97 |
Cl2—C5 | 1.742 (2) | C7—H4 | 0.97 |
O1—C1 | 1.230 (3) | C8—C9 | 1.498 (5) |
O2—C3 | 1.256 (3) | C8—H6 | 0.97 |
O3—C4 | 1.238 (3) | C8—H5 | 0.97 |
O4—C6 | 1.259 (3) | C9—C10 | 1.502 (5) |
N1—C7 | 1.495 (3) | C9—H8 | 0.97 |
N1—C10 | 1.495 (3) | C9—H7 | 0.97 |
N1—H1 | 0.89 | C10—H9 | 0.97 |
N1—H2 | 0.89 | C10—H10 | 0.97 |
N2—C11 | 1.497 (3) | C11—C12 | 1.482 (4) |
N2—C14 | 1.499 (3) | C11—H13 | 0.97 |
N2—H11 | 0.89 | C11—H14 | 0.97 |
N2—H12 | 0.89 | C12—C13 | 1.510 (5) |
C1—C2 | 1.416 (3) | C12—H16 | 0.97 |
C1—C6 | 1.544 (3) | C12—H15 | 0.97 |
C2—C3 | 1.382 (3) | C13—C14 | 1.516 (4) |
C3—C4 | 1.540 (3) | C13—H18 | 0.97 |
C4—C5 | 1.415 (3) | C13—H17 | 0.97 |
C5—C6 | 1.384 (3) | C14—H19 | 0.97 |
C7—C8 | 1.487 (4) | C14—H20 | 0.97 |
| | | |
O1···N1i | 2.962 (3) | O3···N2 | 2.930 (3) |
O2···N1 | 2.791 (3) | O4···N2i | 2.783 (3) |
O2···N2 | 2.841 (3) | O4···N1i | 2.824 (3) |
| | | |
C3—C2—Cl1 | 118.52 (18) | C7—C8—H6 | 110.9 |
C1—C2—Cl1 | 117.3 (2) | C9—C8—H6 | 110.9 |
C6—C5—Cl2 | 118.77 (17) | H5—C8—H6 | 108.9 |
C4—C5—Cl2 | 117.4 (2) | C8—C9—C10 | 104.8 (3) |
O1—C1—C2 | 125.1 (2) | C8—C9—H7 | 110.8 |
O1—C1—C6 | 117.1 (2) | C10—C9—H7 | 110.8 |
O2—C3—C2 | 126.1 (2) | C8—C9—H8 | 110.8 |
O2—C3—C4 | 116.1 (2) | C10—C9—H8 | 110.8 |
O3—C4—C5 | 124.9 (2) | H7—C9—H8 | 108.9 |
O3—C4—C3 | 116.9 (2) | N1—C10—C9 | 104.8 (2) |
O4—C6—C5 | 125.9 (2) | N1—C10—H9 | 110.8 |
O4—C6—C1 | 116.1 (2) | C9—C10—H9 | 110.8 |
C1—C2—C3 | 124.1 (2) | N1—C10—H10 | 110.8 |
C2—C3—C4 | 117.8 (2) | C9—C10—H10 | 110.8 |
C3—C4—C5 | 118.2 (2) | H9—C10—H10 | 108.9 |
C4—C5—C6 | 123.8 (2) | C12—C11—N2 | 106.9 (2) |
C5—C6—C1 | 117.96 (19) | C12—C11—H13 | 110.3 |
C2—C1—C6 | 117.82 (19) | N2—C11—H13 | 110.3 |
C7—N1—C10 | 108.4 (2) | C12—C11—H14 | 110.3 |
C7—N1—H1 | 110.0 | N2—C11—H14 | 110.3 |
C10—N1—H1 | 110.0 | H13—C11—H14 | 108.6 |
C7—N1—H2 | 110.0 | C11—C12—C13 | 105.6 (3) |
C10—N1—H2 | 110.0 | C11—C12—H15 | 110.6 |
H1—N1—H2 | 108.4 | C13—C12—H15 | 110.6 |
C11—N2—C14 | 108.0 (2) | C11—C12—H16 | 110.6 |
C11—N2—H11 | 110.1 | C13—C12—H16 | 110.6 |
C14—N2—H11 | 110.1 | H15—C12—H16 | 108.7 |
C11—N2—H12 | 110.1 | C12—C13—C14 | 104.5 (2) |
C14—N2—H12 | 110.1 | C12—C13—H17 | 110.9 |
H11—N2—H12 | 108.4 | C14—C13—H17 | 110.9 |
C8—C7—N1 | 104.5 (2) | C12—C13—H18 | 110.9 |
C8—C7—H3 | 110.8 | C14—C13—H18 | 110.9 |
N1—C7—H3 | 110.8 | H17—C13—H18 | 108.9 |
C8—C7—H4 | 110.8 | N2—C14—C13 | 103.2 (2) |
N1—C7—H4 | 110.8 | N2—C14—H19 | 111.1 |
H3—C7—H4 | 108.9 | C13—C14—H19 | 111.1 |
C7—C8—C9 | 104.2 (3) | N2—C14—H20 | 111.1 |
C7—C8—H5 | 110.9 | C13—C14—H20 | 111.1 |
C9—C8—H5 | 110.9 | H19—C14—H20 | 109.1 |
| | | |
O1—C1—C2—C3 | 179.5 (3) | C2—C3—C4—C5 | −3.4 (4) |
O1—C1—C2—Cl1 | 1.8 (4) | C3—C4—C5—C6 | −1.0 (4) |
O1—C1—C6—O4 | −2.5 (4) | C3—C4—C5—Cl2 | −177.8 (2) |
O1—C1—C6—C5 | 176.0 (3) | C4—C5—C6—O4 | −177.0 (3) |
O2—C3—C4—C5 | 176.8 (3) | C4—C5—C6—C1 | 4.6 (4) |
O2—C3—C4—O3 | −3.3 (4) | C6—C1—C2—C3 | −0.4 (4) |
O3—C4—C5—C6 | 179.1 (3) | C6—C1—C2—Cl1 | −178.1 (2) |
O3—C4—C5—Cl2 | 2.3 (4) | N1—C7—C8—C9 | 32.9 (3) |
Cl1—C2—C3—O2 | 1.4 (4) | C7—C8—C9—C10 | −36.9 (3) |
Cl1—C2—C3—C4 | −178.3 (2) | C8—C9—C10—N1 | 26.0 (3) |
Cl2—C5—C6—O4 | −0.2 (4) | C7—N1—C10—C9 | −5.6 (3) |
Cl2—C5—C6—C1 | −178.60 (19) | C10—N1—C7—C8 | −16.9 (3) |
C1—C2—C3—O2 | −176.3 (3) | N2—C11—C12—C13 | −17.2 (4) |
C1—C2—C3—C4 | 4.0 (4) | C11—C12—C13—C14 | 32.0 (4) |
C2—C1—C6—O4 | 177.4 (2) | C12—C13—C14—N2 | −33.9 (3) |
C2—C3—C4—O3 | 176.5 (3) | C11—N2—C14—C13 | 23.7 (3) |
C2—C1—C6—C5 | −4.0 (4) | C14—N2—C11—C12 | −4.3 (4) |
Symmetry code: (i) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.89 | 1.91 | 2.791 (3) | 169 |
N1—H2···O1ii | 0.89 | 2.39 | 2.962 (3) | 122 |
N1—H2···O4ii | 0.89 | 1.98 | 2.824 (3) | 158 |
N2—H11···O2 | 0.89 | 2.12 | 2.841 (3) | 138 |
N2—H11···O3 | 0.89 | 2.26 | 2.930 (2) | 132 |
N2—H12···O4ii | 0.89 | 1.96 | 2.783 (3) | 153 |
Symmetry code: (ii) x−1, y, z. |