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access3-Chloroquinuclidinium chloride
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
The cation of the title compound, C7H13ClN+·Cl−, forms a linear hydrogen bond to the chloride anion. The cation is disordered about a mirror plane.
Related literature
For isomeric 4-chloroquinuclidinium chloride, see: Kurahashi et al. (1980![[Kurahashi, M., Engel, P. & Nowacki, W. (1980). Z. Kristallogr. 152, 147-156.]](../../../../../../logos/arrows/e_arr.gif "Kurahashi, M., Engel, P. & Nowacki, W. (1980). Z. Kristallogr. 152, 147-156.")
), which also reports the parent quinuclidinium chloride.
![[Scheme 1]](bq2068scheme1.gif)
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
Supporting information
contains datablocks global, I. DOI: 10.1107/S1600536808011434/bq2068sup1.cif
Structure factors: contains datablock I. DOI: 10.1107/S1600536808011434/bq2068Isup2.hkl
The commercially available compound was a crystalline. A large block was cut into a smaller specimen.
The cation is disordered about a mirror plane in the carbon atoms except C1 atom. The N1 and C1 atoms, which lie on this were refined with their normal half occupancies. The other carbon atoms were refined with half occupancies, subject to N–C being restrained to 1.49±0.01 Å and C–C to 1.54±0.01 Å. Additionally, the 1,3-related distances were restrained from 2.43±0.01 Å, to 2.47±0.01 Å as well as 2.52±-0.01 Å. The anisotropic temperature factors of the disordered carbon were restrained to be nearly isotropic but the N–H distance was restrained to 0.88±0.01 Å.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.99 to 1.00 Å) and were included in the in the riding model approximation, with U(H) set to 1.2U(C). The ammonium H-atom was located in a difference Fourier map, and was refined with an N–H distance restraint of 0.88±0.01 Å; its temperature factor was freely refined.
Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
![[Figure 1]](./bq2068fig1thm.gif) | Fig. 1. Thermal ellipsoid plot of the two independent molecules of 2-chloroquinuclidinium chloride at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The dashed lines denote the hydrogen bond. |
| C7H13ClN+·Cl− | F(000) = 392 |
| Mr = 182.10 | Dx = 1.408 Mg m−3 |
| Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2n | Cell parameters from 909 reflections |
| a = 9.379 (1) Å | θ = 3.1–22.9° |
| b = 8.067 (1) Å | µ = 0.68 mm−1 |
| c = 11.482 (2) Å | T = 100 K |
| V = 868.7 (2) Å3 | Block, colorless |
| Z = 4 | 0.15 × 0.08 × 0.03 mm |
| Bruker SMART APEX diffractometer | 1068 independent reflections |
| Radiation source: fine-focus sealed tube | 856 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.047 |
| ϕ and ω scans | θmax = 27.5°, θmin = 2.8° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→8 |
| Tmin = 0.872, Tmax = 1.000 | k = −10→10 |
| 5307 measured reflections | l = −14→13 |
| 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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0562P)2 + 0.8408P] where P = (Fo2 + 2Fc2)/3 |
| 1068 reflections | (Δ/σ)max = 0.001 |
| 82 parameters | Δρmax = 0.31 e Å−3 |
| 58 restraints | Δρmin = −0.57 e Å−3 |
| C7H13ClN+·Cl− | V = 868.7 (2) Å3 |
| Mr = 182.10 | Z = 4 |
| Orthorhombic, Pnma | Mo Kα radiation |
| a = 9.379 (1) Å | µ = 0.68 mm−1 |
| b = 8.067 (1) Å | T = 100 K |
| c = 11.482 (2) Å | 0.15 × 0.08 × 0.03 mm |
| Bruker SMART APEX diffractometer | 1068 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 856 reflections with I > 2σ(I) |
| Tmin = 0.872, Tmax = 1.000 | Rint = 0.047 |
| 5307 measured reflections |
| R[F2 > 2σ(F2)] = 0.039 | 58 restraints |
| wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.02 | Δρmax = 0.31 e Å−3 |
| 1068 reflections | Δρmin = −0.57 e Å−3 |
| 82 parameters |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| Cl1 | 0.69230 (8) | 0.2500 | 0.57828 (7) | 0.0218 (2) | |
| Cl2 | 0.10483 (11) | 0.2500 | 0.30411 (8) | 0.0374 (3) | |
| N1 | 0.3718 (3) | 0.2500 | 0.5682 (2) | 0.0190 (6) | |
| H1 | 0.4648 (12) | 0.2500 | 0.576 (3) | 0.035 (12)* | |
| C1 | 0.3382 (3) | 0.2500 | 0.4416 (3) | 0.0331 (9) | |
| H1A | 0.4092 | 0.1832 | 0.3983 | 0.040* | 0.50 |
| H1B | 0.3397 | 0.3645 | 0.4106 | 0.040* | 0.50 |
| C2 | 0.1846 (4) | 0.1722 (5) | 0.4282 (3) | 0.0184 (9) | 0.50 |
| H2 | 0.1947 | 0.0495 | 0.4194 | 0.022* | |
| C3 | 0.2957 (7) | 0.3924 (13) | 0.6253 (9) | 0.0204 (17) | 0.50 |
| H3A | 0.3397 | 0.4988 | 0.6019 | 0.024* | 0.50 |
| H3B | 0.3013 | 0.3825 | 0.7111 | 0.024* | 0.50 |
| C4 | 0.1402 (5) | 0.3855 (6) | 0.5851 (5) | 0.0212 (11) | 0.50 |
| H4A | 0.1248 | 0.4653 | 0.5209 | 0.025* | 0.50 |
| H4B | 0.0763 | 0.4159 | 0.6503 | 0.025* | 0.50 |
| C5 | 0.3285 (7) | 0.0917 (13) | 0.6251 (10) | 0.024 (2) | 0.50 |
| H5A | 0.3698 | 0.0857 | 0.7043 | 0.029* | 0.50 |
| H5B | 0.3651 | −0.0034 | 0.5795 | 0.029* | 0.50 |
| C6 | 0.1650 (5) | 0.0823 (7) | 0.6325 (4) | 0.0244 (12) | 0.50 |
| H6A | 0.1323 | 0.1111 | 0.7120 | 0.029* | 0.50 |
| H6B | 0.1316 | −0.0310 | 0.6139 | 0.029* | 0.50 |
| C7 | 0.1058 (4) | 0.2079 (5) | 0.5430 (4) | 0.0205 (12) | 0.50 |
| H7 | 0.0007 | 0.1931 | 0.5330 | 0.025* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Cl1 | 0.0157 (4) | 0.0284 (4) | 0.0212 (4) | 0.000 | −0.0006 (3) | 0.000 |
| Cl2 | 0.0340 (5) | 0.0546 (6) | 0.0236 (5) | 0.000 | −0.0111 (4) | 0.000 |
| N1 | 0.0145 (13) | 0.0241 (13) | 0.0184 (14) | 0.000 | −0.0020 (10) | 0.000 |
| C1 | 0.0176 (17) | 0.064 (3) | 0.0182 (19) | 0.000 | 0.0006 (13) | 0.000 |
| C2 | 0.019 (2) | 0.0171 (19) | 0.019 (2) | 0.0018 (17) | −0.0032 (16) | 0.0013 (17) |
| C3 | 0.019 (3) | 0.017 (3) | 0.025 (3) | −0.004 (3) | 0.008 (3) | 0.004 (2) |
| C4 | 0.015 (2) | 0.022 (3) | 0.026 (3) | 0.004 (2) | −0.004 (2) | −0.006 (2) |
| C5 | 0.017 (3) | 0.019 (3) | 0.036 (4) | 0.000 (3) | 0.007 (3) | −0.001 (3) |
| C6 | 0.028 (3) | 0.026 (3) | 0.019 (3) | −0.003 (2) | −0.002 (2) | 0.004 (2) |
| C7 | 0.0108 (17) | 0.030 (4) | 0.021 (2) | −0.0037 (16) | 0.0014 (15) | −0.0070 (18) |
| Cl2—C2 | 1.727 (4) | C3—H3B | 0.9900 |
| N1—C5 | 1.491 (7) | C4—C7 | 1.546 (6) |
| N1—C1 | 1.488 (4) | C4—H4A | 0.9900 |
| N1—C3 | 1.502 (7) | C4—H4B | 0.9900 |
| N1—H1 | 0.88 (1) | C5—C6 | 1.538 (7) |
| C1—C2 | 1.579 (4) | C5—H5A | 0.9900 |
| C1—H1A | 0.9900 | C5—H5B | 0.9900 |
| C1—H1B | 0.9900 | C6—C7 | 1.546 (5) |
| C2—C7 | 1.539 (5) | C6—H6A | 0.9900 |
| C2—H2 | 1.0000 | C6—H6B | 0.9900 |
| C3—C4 | 1.531 (7) | C7—H7 | 1.0000 |
| C3—H3A | 0.9900 | ||
| C5—N1—C1 | 111.7 (5) | C3—C4—C7 | 109.1 (4) |
| C5—N1—C3 | 109.5 (3) | C3—C4—H4A | 109.9 |
| C1—N1—C3 | 109.0 (4) | C7—C4—H4A | 109.9 |
| C5—N1—H1 | 103.1 (13) | C3—C4—H4B | 109.9 |
| C1—N1—H1 | 108 (3) | C7—C4—H4B | 109.9 |
| C3—N1—H1 | 115.3 (14) | H4A—C4—H4B | 108.3 |
| N1—C1—C2 | 106.8 (2) | N1—C5—C6 | 109.8 (5) |
| N1—C1—H1A | 110.4 | N1—C5—H5A | 109.7 |
| C2—C1—H1A | 110.4 | C6—C5—H5A | 109.7 |
| N1—C1—H1B | 110.4 | N1—C5—H5B | 109.7 |
| C2—C1—H1B | 110.4 | C6—C5—H5B | 109.7 |
| H1A—C1—H1B | 108.6 | H5A—C5—H5B | 108.2 |
| C7—C2—C1 | 106.3 (3) | C5—C6—C7 | 106.8 (4) |
| C7—C2—Cl2 | 115.5 (3) | C5—C6—H6A | 110.4 |
| C1—C2—Cl2 | 109.4 (2) | C7—C6—H6A | 110.4 |
| C7—C2—H2 | 108.5 | C5—C6—H6B | 110.4 |
| C1—C2—H2 | 108.5 | C7—C6—H6B | 110.4 |
| Cl2—C2—H2 | 108.5 | H6A—C6—H6B | 108.6 |
| N1—C3—C4 | 107.1 (4) | C2—C7—C4 | 109.9 (3) |
| N1—C3—H3A | 110.3 | C2—C7—C6 | 106.0 (3) |
| C4—C3—H3A | 110.3 | C4—C7—C6 | 108.9 (3) |
| N1—C3—H3B | 110.3 | C2—C7—H7 | 110.6 |
| C4—C3—H3B | 110.3 | C4—C7—H7 | 110.6 |
| H3A—C3—H3B | 108.6 | C6—C7—H7 | 110.6 |
| C5—N1—C1—C2 | 42.7 (4) | N1—C5—C6—C7 | 18.9 (10) |
| C3—N1—C1—C2 | −78.5 (4) | C1—C2—C7—C4 | 40.7 (4) |
| N1—C1—C2—C7 | 27.3 (3) | Cl2—C2—C7—C4 | −80.8 (4) |
| N1—C1—C2—Cl2 | 152.63 (17) | C1—C2—C7—C6 | −76.9 (4) |
| C5—N1—C3—C4 | −73.4 (6) | Cl2—C2—C7—C6 | 161.6 (3) |
| C1—N1—C3—C4 | 49.1 (8) | C3—C4—C7—C2 | −70.0 (6) |
| N1—C3—C4—C7 | 21.4 (9) | C3—C4—C7—C6 | 45.7 (6) |
| C1—N1—C5—C6 | −71.2 (9) | C5—C6—C7—C2 | 49.6 (7) |
| C3—N1—C5—C6 | 49.7 (7) | C5—C6—C7—C4 | −68.6 (7) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···Cl1 | 0.88 (1) | 2.13 (1) | 3.008 (3) | 175 (4) |
Experimental details
| Crystal data | |
| Chemical formula | C7H13ClN+·Cl− |
| Mr | 182.10 |
| Crystal system, space group | Orthorhombic, Pnma |
| Temperature (K) | 100 |
| a, b, c (Å) | 9.379 (1), 8.067 (1), 11.482 (2) |
| V (Å3) | 868.7 (2) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.68 |
| Crystal size (mm) | 0.15 × 0.08 × 0.03 |
| Data collection | |
| Diffractometer | Bruker SMART APEX diffractometer |
| Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
| Tmin, Tmax | 0.872, 1.000 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 5307, 1068, 856 |
| Rint | 0.047 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.113, 1.02 |
| No. of reflections | 1068 |
| No. of parameters | 82 |
| No. of restraints | 58 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.31, −0.57 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1···Cl1 | 0.88 (1) | 2.13 (1) | 3.008 (3) | 175 (4) |
Acknowledgements
We thank the University of Malaya for the purchase of the diffractometer.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kurahashi, M., Engel, P. & Nowacki, W. (1980). Z. Kristallogr. 152, 147–156. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
4-Chloroquinuclidinium chloride features an N–H···Cl hydrogen bond between the cation and anion. The N–C and C–C bonds are somewhat shorter than those in the unsubstituted salt, and this has been attributed to the electron-withdrawing effect of the chlorine substituent (Kurahashi et al., 1980). The present isomeric compound (Scheme I) is expected to show this feature; however, owing to disorder, the effect cannot be unambiguously observed even at low temperature. The cation forms a linear hydrogen bond [N–H···Cl 3.008 (3) Å] to the chloride; the cation is disordered about a mirror plane (Fig. 1).