Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, 2C4H10N+·C6Cl2O42−, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010724/fl6097sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010724/fl6097Isup2.hkl
Contains datablock I

CCDC reference: 242316

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](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

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
2C4H10N+·C6Cl2O42Z = 2
Mr = 351.23F(000) = 368
Triclinic, P1Dx = 1.486 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.337 (3) ÅCell parameters from 25 reflections
b = 9.601 (4) Åθ = 11.2–11.8°
c = 9.947 (5) ŵ = 0.43 mm1
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 anodeRint = 0.014
Graphite monochromatorθmax = 27.5°, θmin = 2.2°
ω–2θ scansh = 1211
Absorption correction: ψ scan
(North et al., 1968)
k = 120
Tmin = 0.91, Tmax = 0.94l = 1211
3821 measured reflections3 standard reflections every 97 reflections
3606 independent reflections intensity decay: 1.7%
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-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 parametersΔρmax = 0.57 e Å3
0 restraintsΔρmin = 0.36 e Å3
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
xyzUiso*/Ueq
Cl10.58538 (7)0.46619 (8)0.27994 (7)0.0446 (2)
Cl20.97853 (7)0.05581 (7)0.26667 (7)0.03732 (19)
O10.8969 (2)0.4251 (2)0.1949 (2)0.0411 (5)
O20.50354 (19)0.1967 (2)0.0502 (2)0.0385 (4)
O30.6647 (2)0.0101 (2)0.1850 (2)0.0467 (5)
O41.06977 (18)0.1996 (2)0.02585 (19)0.0354 (4)
N10.2269 (2)0.3741 (2)0.1955 (2)0.0303 (4)
N20.3348 (2)0.0689 (2)0.1923 (2)0.0314 (4)
C10.8398 (2)0.3259 (3)0.1127 (3)0.0276 (5)
C20.6923 (3)0.3220 (3)0.1289 (3)0.0299 (5)
C30.6307 (2)0.2088 (3)0.0358 (3)0.0276 (5)
C40.7248 (3)0.0854 (3)0.0992 (3)0.0289 (5)
C50.8720 (2)0.0892 (3)0.1164 (2)0.0263 (5)
C60.9374 (2)0.1960 (3)0.0178 (2)0.0257 (5)
C70.2171 (3)0.3986 (3)0.3521 (3)0.0406 (6)
C80.1290 (4)0.5672 (4)0.4214 (3)0.0580 (9)
C90.1724 (4)0.6469 (4)0.3351 (4)0.0655 (10)
C100.1888 (3)0.5317 (3)0.1819 (3)0.0446 (7)
C110.3088 (4)0.2129 (3)0.2286 (3)0.0491 (7)
C120.3053 (5)0.1620 (4)0.3887 (4)0.0667 (10)
C130.2807 (4)0.0022 (4)0.4415 (3)0.0545 (8)
C140.3588 (3)0.0702 (3)0.3314 (3)0.0382 (6)
H10.31980.31640.16070.045*
H20.16260.32350.14510.045*
H30.31690.37690.39290.061*
H40.16570.33090.36500.061*
H50.15570.60870.52210.087*
H60.02140.58080.41620.087*
H70.26680.66930.36830.098*
H80.09460.74480.34290.098*
H90.26890.53710.13060.067*
H100.09540.55290.13030.067*
H110.41550.05690.13710.047*
H120.25520.07800.14380.047*
H130.38960.25950.19140.074*
H140.21380.29030.18620.074*
H150.39990.15490.42710.100*
H160.22370.23580.41860.100*
H170.32520.06140.53740.082*
H180.17380.01240.44460.082*
H190.46550.12180.35490.057*
H200.31320.14590.32620.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0321 (3)0.0451 (4)0.0429 (4)0.0121 (3)0.0090 (3)0.0021 (3)
Cl20.0291 (3)0.0395 (4)0.0350 (3)0.0069 (2)0.0059 (2)0.0055 (3)
O10.0301 (9)0.0376 (10)0.0496 (11)0.0181 (8)0.0002 (8)0.0026 (8)
O20.0237 (8)0.0473 (11)0.0415 (10)0.0170 (8)0.0046 (7)0.0062 (8)
O30.0292 (9)0.0460 (11)0.0511 (12)0.0193 (8)0.0033 (8)0.0051 (9)
O40.0220 (8)0.0418 (10)0.0406 (10)0.0133 (7)0.0042 (7)0.0087 (8)
N10.0231 (9)0.0318 (10)0.0322 (10)0.0092 (8)0.0012 (8)0.0062 (8)
N20.0259 (10)0.0367 (11)0.0319 (11)0.0103 (9)0.0001 (8)0.0119 (9)
C10.0234 (11)0.0271 (11)0.0335 (12)0.0096 (9)0.0006 (9)0.0105 (10)
C20.0206 (11)0.0307 (12)0.0340 (12)0.0068 (9)0.0039 (9)0.0067 (10)
C30.0186 (10)0.0312 (12)0.0331 (12)0.0074 (9)0.0006 (9)0.0118 (10)
C40.0218 (11)0.0307 (12)0.0342 (12)0.0098 (9)0.0026 (9)0.0109 (10)
C50.0219 (10)0.0282 (11)0.0281 (11)0.0057 (9)0.0014 (8)0.0105 (9)
C60.0194 (10)0.0289 (11)0.0324 (12)0.0080 (9)0.0019 (9)0.0150 (10)
C70.0433 (15)0.0445 (15)0.0331 (13)0.0103 (12)0.0019 (11)0.0149 (12)
C80.056 (2)0.0555 (19)0.0408 (17)0.0045 (16)0.0043 (14)0.0020 (14)
C90.062 (2)0.0315 (15)0.089 (3)0.0111 (15)0.0076 (19)0.0075 (17)
C100.0382 (15)0.0500 (17)0.0574 (18)0.0163 (13)0.0035 (13)0.0307 (15)
C110.0573 (19)0.0373 (15)0.0547 (18)0.0114 (13)0.0033 (14)0.0200 (13)
C120.087 (3)0.066 (2)0.054 (2)0.016 (2)0.0006 (18)0.0357 (18)
C130.0556 (19)0.073 (2)0.0380 (15)0.0246 (17)0.0067 (13)0.0199 (15)
C140.0343 (13)0.0342 (13)0.0387 (14)0.0100 (11)0.0019 (11)0.0045 (11)
Geometric parameters (Å, º) top
Cl1—C21.746 (3)C7—H30.97
Cl2—C51.742 (2)C7—H40.97
O1—C11.230 (3)C8—C91.498 (5)
O2—C31.256 (3)C8—H60.97
O3—C41.238 (3)C8—H50.97
O4—C61.259 (3)C9—C101.502 (5)
N1—C71.495 (3)C9—H80.97
N1—C101.495 (3)C9—H70.97
N1—H10.89C10—H90.97
N1—H20.89C10—H100.97
N2—C111.497 (3)C11—C121.482 (4)
N2—C141.499 (3)C11—H130.97
N2—H110.89C11—H140.97
N2—H120.89C12—C131.510 (5)
C1—C21.416 (3)C12—H160.97
C1—C61.544 (3)C12—H150.97
C2—C31.382 (3)C13—C141.516 (4)
C3—C41.540 (3)C13—H180.97
C4—C51.415 (3)C13—H170.97
C5—C61.384 (3)C14—H190.97
C7—C81.487 (4)C14—H200.97
O1···N1i2.962 (3)O3···N22.930 (3)
O2···N12.791 (3)O4···N2i2.783 (3)
O2···N22.841 (3)O4···N1i2.824 (3)
C3—C2—Cl1118.52 (18)C7—C8—H6110.9
C1—C2—Cl1117.3 (2)C9—C8—H6110.9
C6—C5—Cl2118.77 (17)H5—C8—H6108.9
C4—C5—Cl2117.4 (2)C8—C9—C10104.8 (3)
O1—C1—C2125.1 (2)C8—C9—H7110.8
O1—C1—C6117.1 (2)C10—C9—H7110.8
O2—C3—C2126.1 (2)C8—C9—H8110.8
O2—C3—C4116.1 (2)C10—C9—H8110.8
O3—C4—C5124.9 (2)H7—C9—H8108.9
O3—C4—C3116.9 (2)N1—C10—C9104.8 (2)
O4—C6—C5125.9 (2)N1—C10—H9110.8
O4—C6—C1116.1 (2)C9—C10—H9110.8
C1—C2—C3124.1 (2)N1—C10—H10110.8
C2—C3—C4117.8 (2)C9—C10—H10110.8
C3—C4—C5118.2 (2)H9—C10—H10108.9
C4—C5—C6123.8 (2)C12—C11—N2106.9 (2)
C5—C6—C1117.96 (19)C12—C11—H13110.3
C2—C1—C6117.82 (19)N2—C11—H13110.3
C7—N1—C10108.4 (2)C12—C11—H14110.3
C7—N1—H1110.0N2—C11—H14110.3
C10—N1—H1110.0H13—C11—H14108.6
C7—N1—H2110.0C11—C12—C13105.6 (3)
C10—N1—H2110.0C11—C12—H15110.6
H1—N1—H2108.4C13—C12—H15110.6
C11—N2—C14108.0 (2)C11—C12—H16110.6
C11—N2—H11110.1C13—C12—H16110.6
C14—N2—H11110.1H15—C12—H16108.7
C11—N2—H12110.1C12—C13—C14104.5 (2)
C14—N2—H12110.1C12—C13—H17110.9
H11—N2—H12108.4C14—C13—H17110.9
C8—C7—N1104.5 (2)C12—C13—H18110.9
C8—C7—H3110.8C14—C13—H18110.9
N1—C7—H3110.8H17—C13—H18108.9
C8—C7—H4110.8N2—C14—C13103.2 (2)
N1—C7—H4110.8N2—C14—H19111.1
H3—C7—H4108.9C13—C14—H19111.1
C7—C8—C9104.2 (3)N2—C14—H20111.1
C7—C8—H5110.9C13—C14—H20111.1
C9—C8—H5110.9H19—C14—H20109.1
O1—C1—C2—C3179.5 (3)C2—C3—C4—C53.4 (4)
O1—C1—C2—Cl11.8 (4)C3—C4—C5—C61.0 (4)
O1—C1—C6—O42.5 (4)C3—C4—C5—Cl2177.8 (2)
O1—C1—C6—C5176.0 (3)C4—C5—C6—O4177.0 (3)
O2—C3—C4—C5176.8 (3)C4—C5—C6—C14.6 (4)
O2—C3—C4—O33.3 (4)C6—C1—C2—C30.4 (4)
O3—C4—C5—C6179.1 (3)C6—C1—C2—Cl1178.1 (2)
O3—C4—C5—Cl22.3 (4)N1—C7—C8—C932.9 (3)
Cl1—C2—C3—O21.4 (4)C7—C8—C9—C1036.9 (3)
Cl1—C2—C3—C4178.3 (2)C8—C9—C10—N126.0 (3)
Cl2—C5—C6—O40.2 (4)C7—N1—C10—C95.6 (3)
Cl2—C5—C6—C1178.60 (19)C10—N1—C7—C816.9 (3)
C1—C2—C3—O2176.3 (3)N2—C11—C12—C1317.2 (4)
C1—C2—C3—C44.0 (4)C11—C12—C13—C1432.0 (4)
C2—C1—C6—O4177.4 (2)C12—C13—C14—N233.9 (3)
C2—C3—C4—O3176.5 (3)C11—N2—C14—C1323.7 (3)
C2—C1—C6—C54.0 (4)C14—N2—C11—C124.3 (4)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.891.912.791 (3)169
N1—H2···O1ii0.892.392.962 (3)122
N1—H2···O4ii0.891.982.824 (3)158
N2—H11···O20.892.122.841 (3)138
N2—H11···O30.892.262.930 (2)132
N2—H12···O4ii0.891.962.783 (3)153
Symmetry code: (ii) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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