Anion–anion dimerization in tetra­butyl­ammonium hydrogen­sulfate

Light, M.E.; Gale, P.A.; Hursthouse, M.B.

doi:10.1107/S1600536801011321

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Anion-anion dimerization in tetrabutylammonium hydrogensulfate

M. E. Light, P. A. Gale and M. B. Hursthouse

The hydrogensulfate ions of the title compound, C₁₆H₃₆N⁺·HSO₄^-, form hydrogen-bonded dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011321/bt6059sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011321/bt6059Isup2.hkl Contains datablock I

CCDC reference: 170897

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.007 Å
R factor = 0.073
wR factor = 0.237
Data-to-parameter ratio = 17.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



DIFMX_01  Alert C The maximum difference density is > 0.1*ZMAX*0.75
          _refine_diff_density_max given =      1.256
          Test value =      1.200

DIFMX_02  Alert C The minimum difference density is > 0.1*ZMAX*0.75
          The relevant atom site should be identified.

PLAT_320  Alert C Check Hybridisation of  C(12)  in main residue          ?

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(11)  -   C(12)  =       1.35 Ang.

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(31)  -   C(32)  =       1.39 Ang.

PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(39)  -   C(40)  =       1.40 Ang.

PLAT_361  Alert C Long   C(sp3)-C(sp3) Bond  C(30)  -   C(31)  =       1.66 Ang.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 7 Alert Level C = Please check

Comment top

The development of receptors and sensors for anions is a rapidly developing area in supramolecular chemistry. (Atwood et al., 1996; Beer & Gale, 2001; Beer & Smith, 1997; Bianchi et al., 1997; Davis et al., 1996; Kavallieratos et al., 1997; Schmidtchen & Berger, 1997; Sessler & Allen, 1999). In addition, anions have recently been exploited as templates for the formation of self-assembled supramolecular architectures in both organic and inorganic systems (Gale, 2000, 2001). By drawing an analogy to carboxylic acid structures in the solid state (Bruno & Randaccio, 1980), one might expect the hydrogensulfate anions to dimerize via the formation of two hydrogen bonds. This anion dimer assembly has been observed in the tetramethylammonium salt (Malchus & Jansen, 1998) as well as in other crystal structures (e.g. Toma et al., 1994), however, not in the tetrabutylammonium salts that are commonly used in anion complexation studies.

The title compound, (I), crystallizes in a large monoclinic cell (Fig. 2) with four tetrabutylammonium ions and four hydrogensulfate ions in the asymmetric unit. Each hydrogensulfate ion donates and accepts a hydrogen bond (Fig. 2) to form the two dimers present in the asymmetric unit.

Experimental top

The title compound was obtained from the Aldrich Chemical Company.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: SCALEPACK (Otwinoski & Minor, 1997) and COLLECT; data reduction: DENZO, COLLECT maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1993); software used to prepare material for publication: WinGX (Farrugia, 1998).

Figures top

	Fig. 1. Displacement ellipsoid plot of the anion–cation pairs. The ellipses are drawn at the 30% probablity level and the H atoms on the tetrabutylammonium cation have been omitted for clarity.
	Fig. 2. Packing diagram showing the arrangement of the four tetrabutylammonium ions in the unit cell.

Tetrabutylammonium sulfate top

Crystal data top

C₁₆H₃₆N⁺·HSO₄⁻	F(000) = 3008
M_r = 339.53	D_x = 1.136 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.7299 (4) Å	Cell parameters from 38718 reflections
b = 21.3998 (4) Å	θ = 2.9–25.0°
c = 17.0880 (4) Å	µ = 0.18 mm⁻¹
β = 91.318 (3)°	T = 120 K
V = 7944.1 (3) Å³	Block, colourless
Z = 16	0.10 × 0.10 × 0.10 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	13981 independent reflections
Radiation source: Nonius FR591 rotating anode	8004 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.068
Detector resolution: 9.091 pixels mm¹ pixels mm^-1	θ_max = 25.0°, θ_min = 2.9°
ϕ and ω scans to fill the Ewald sphere	h = −25→25
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	k = −25→24
T_min = 0.982, T_max = 0.982	l = −20→20
38718 measured reflections

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.237	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1368P)² + 1.0999P] where P = (F_o² + 2F_c²)/3
13981 reflections	(Δ/σ)_max < 0.001
809 parameters	Δρ_max = 1.26 e Å⁻³
19 restraints	Δρ_min = −0.70 e Å⁻³

Crystal data top

C₁₆H₃₆N⁺·HSO₄⁻	V = 7944.1 (3) Å³
M_r = 339.53	Z = 16
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.7299 (4) Å	µ = 0.18 mm⁻¹
b = 21.3998 (4) Å	T = 120 K
c = 17.0880 (4) Å	0.10 × 0.10 × 0.10 mm
β = 91.318 (3)°

Data collection top

Nonius KappaCCD area-detector diffractometer	13981 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	8004 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.982	R_int = 0.068
38718 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	19 restraints
wR(F²) = 0.237	H-atom parameters constrained
S = 1.02	Δρ_max = 1.26 e Å⁻³
13981 reflections	Δρ_min = −0.70 e Å⁻³
809 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.36857 (18)	−0.04267 (19)	0.6738 (2)	0.0333 (10)
H1A	0.3608	0.0006	0.6916	0.040*
H1B	0.3283	−0.0639	0.6683	0.040*
C2	0.3981 (2)	−0.0400 (2)	0.5933 (2)	0.0397 (11)
H2A	0.4368	−0.0157	0.5971	0.048*
H2B	0.4083	−0.0829	0.5760	0.048*
C3	0.3544 (2)	−0.0097 (2)	0.5337 (2)	0.0556 (14)
H3A	0.3456	0.0338	0.5498	0.067*
H3B	0.3151	−0.0330	0.5314	0.067*
C4	0.3831 (3)	−0.0095 (2)	0.4526 (3)	0.0666 (16)
H4A	0.3546	0.0103	0.4148	0.100*
H4B	0.3912	−0.0525	0.4363	0.100*
H4C	0.4218	0.0140	0.4548	0.100*
C5	0.41941 (18)	−0.14302 (17)	0.7129 (2)	0.0329 (10)
H5A	0.4416	−0.1639	0.7569	0.040*
H5B	0.4471	−0.1427	0.6678	0.040*
C6	0.3630 (2)	−0.18176 (19)	0.6913 (3)	0.0521 (13)
H6A	0.3450	−0.1667	0.6409	0.062*
H6B	0.3316	−0.1766	0.7319	0.062*
C7	0.3797 (2)	−0.2510 (2)	0.6839 (3)	0.0507 (13)
H7A	0.3454	−0.2731	0.6568	0.061*
H7B	0.4164	−0.2548	0.6510	0.061*
C8	0.3927 (3)	−0.2819 (2)	0.7599 (3)	0.0689 (16)
H8A	0.4035	−0.3257	0.7509	0.103*
H8B	0.3560	−0.2798	0.7922	0.103*
H8C	0.4270	−0.2607	0.7869	0.103*
C9	0.46913 (17)	−0.04597 (18)	0.7482 (2)	0.0310 (10)
H9A	0.4922	−0.0501	0.6992	0.037*
H9B	0.4921	−0.0694	0.7895	0.037*
C10	0.4680 (2)	0.02283 (18)	0.7712 (3)	0.0405 (11)
H10A	0.4432	0.0462	0.7316	0.049*
H10B	0.4474	0.0270	0.8220	0.049*
C11	0.5864 (2)	0.0311 (3)	0.7668 (4)	0.0838 (19)
H11A	0.6153	0.0608	0.7913	0.126*
H11B	0.5940	0.0286	0.7106	0.126*
H11C	0.5921	−0.0102	0.7906	0.126*
C12	0.5282 (3)	0.0506 (3)	0.7777 (5)	0.124 (3)
H12A	0.5247	0.0879	0.7436	0.149*
H12B	0.5297	0.0672	0.8318	0.149*
C13	0.37032 (19)	−0.07383 (19)	0.8109 (2)	0.0357 (10)
H13A	0.3292	−0.0924	0.8004	0.043*
H13B	0.3641	−0.0295	0.8255	0.043*
C14	0.4004 (2)	−0.1078 (3)	0.8804 (3)	0.0573 (14)
H14A	0.4073	−0.1519	0.8655	0.069*
H14B	0.4412	−0.0888	0.8914	0.069*
C15	0.3651 (3)	−0.1066 (3)	0.9522 (3)	0.0662 (15)
H15A	0.3241	−0.1253	0.9412	0.079*
H15B	0.3585	−0.0625	0.9676	0.079*
C16	0.3951 (3)	−0.1406 (3)	1.0196 (3)	0.0727 (17)
H16A	0.3690	−0.1375	1.0655	0.109*
H16B	0.4353	−0.1219	1.0317	0.109*
H16C	0.4004	−0.1847	1.0057	0.109*
C17	0.30977 (19)	0.30363 (18)	0.8920 (2)	0.0332 (10)
H17A	0.3455	0.3130	0.8591	0.040*
H17B	0.2813	0.2768	0.8609	0.040*
C18	0.2772 (2)	0.36423 (19)	0.9095 (2)	0.0433 (12)
H18A	0.3011	0.3879	0.9496	0.052*
H18B	0.2360	0.3553	0.9304	0.052*
C19	0.2705 (3)	0.4036 (2)	0.8341 (3)	0.0542 (13)
H19A	0.2521	0.4444	0.8474	0.065*
H19B	0.3120	0.4117	0.8136	0.065*
C20	0.2316 (3)	0.3733 (2)	0.7706 (3)	0.0674 (16)
H20A	0.2299	0.4005	0.7245	0.101*
H20B	0.1899	0.3666	0.7895	0.101*
H20C	0.2497	0.3330	0.7565	0.101*
C21	0.28150 (18)	0.25479 (18)	1.0204 (2)	0.0292 (9)
H21A	0.2990	0.2312	1.0655	0.035*
H21B	0.2672	0.2956	1.0404	0.035*
C22	0.22641 (19)	0.2194 (2)	0.9880 (2)	0.0370 (10)
H22A	0.2403	0.1800	0.9638	0.044*
H22B	0.2054	0.2447	0.9470	0.044*
C23	0.1817 (2)	0.2048 (3)	1.0525 (3)	0.0660 (16)
H23A	0.1470	0.1801	1.0301	0.079*
H23B	0.2029	0.1787	1.0926	0.079*
C24	0.1563 (3)	0.2620 (4)	1.0915 (3)	0.101 (3)
H24A	0.1279	0.2493	1.1323	0.151*
H24B	0.1343	0.2877	1.0525	0.151*
H24C	0.1902	0.2862	1.1151	0.151*
C25	0.3580 (2)	0.20652 (19)	0.9309 (2)	0.0383 (11)
H25A	0.3922	0.2169	0.8959	0.046*
H25B	0.3254	0.1861	0.8985	0.046*
C26	0.3813 (2)	0.1601 (2)	0.9918 (2)	0.0450 (12)
H26A	0.4129	0.1803	1.0259	0.054*
H26B	0.3468	0.1470	1.0250	0.054*
C27	0.4087 (2)	0.1033 (2)	0.9528 (3)	0.0576 (14)
H27A	0.3776	0.0843	0.9168	0.069*
H27B	0.4442	0.1163	0.9214	0.069*
C28	0.4295 (3)	0.0557 (2)	1.0126 (3)	0.0714 (17)
H28A	0.4479	0.0199	0.9860	0.107*
H28B	0.3940	0.0416	1.0423	0.107*
H28C	0.4601	0.0746	1.0484	0.107*
C29	0.3815 (2)	0.3018 (2)	1.0099 (2)	0.0436 (12)
H29A	0.3616	0.3368	1.0374	0.052*
H29B	0.3990	0.2734	1.0503	0.052*
C30	0.4339 (3)	0.3279 (3)	0.9629 (3)	0.0825 (18)
H30A	0.4177	0.3560	0.9213	0.099*
H30B	0.4569	0.2936	0.9380	0.099*
C31	0.4795 (3)	0.3670 (3)	1.0246 (5)	0.102 (2)
H31A	0.5010	0.4019	0.9988	0.122*
H31B	0.4572	0.3828	1.0704	0.122*
C32	0.5191 (3)	0.3184 (3)	1.0442 (5)	0.119 (3)
H32A	0.5512	0.3335	1.0806	0.179*
H32B	0.5381	0.3024	0.9967	0.179*
H32C	0.4959	0.2848	1.0691	0.179*
C33	0.8174 (2)	0.19501 (19)	0.8964 (2)	0.0374 (10)
H33A	0.7943	0.2250	0.8629	0.045*
H33B	0.8512	0.1778	0.8650	0.045*
C34	0.7750 (2)	0.1425 (2)	0.9165 (3)	0.0531 (13)
H34A	0.7402	0.1590	0.9466	0.064*
H34B	0.7974	0.1118	0.9498	0.064*
C35	0.7502 (3)	0.1100 (2)	0.8423 (3)	0.0586 (14)
H35A	0.7167	0.0811	0.8569	0.070*
H35B	0.7322	0.1419	0.8066	0.070*
C36	0.7974 (3)	0.0743 (3)	0.8002 (3)	0.0849 (19)
H36A	0.7788	0.0559	0.7528	0.127*
H36B	0.8138	0.0411	0.8341	0.127*
H36C	0.8309	0.1025	0.7857	0.127*
C37	0.8846 (2)	0.18735 (19)	1.0175 (2)	0.0380 (11)
H37A	0.9029	0.2124	1.0609	0.046*
H37B	0.8567	0.1563	1.0410	0.046*
C38	0.9355 (2)	0.1527 (2)	0.9783 (3)	0.0484 (12)
H38A	0.9629	0.1824	0.9515	0.058*
H38B	0.9181	0.1233	0.9388	0.058*
C39	0.9715 (3)	0.1168 (3)	1.0415 (3)	0.0738 (18)
H39A	0.9864	0.1471	1.0815	0.089*
H39B	0.9430	0.0878	1.0674	0.089*
C40	1.0220 (4)	0.0825 (4)	1.0159 (5)	0.135 (3)
H40A	1.0413	0.0605	1.0605	0.203*
H40B	1.0520	0.1109	0.9929	0.203*
H40C	1.0081	0.0521	0.9765	0.203*
C41	0.79767 (18)	0.25782 (19)	1.0186 (2)	0.0333 (10)
H41A	0.7746	0.2227	1.0417	0.040*
H41B	0.8190	0.2801	1.0622	0.040*
C42	0.7520 (2)	0.3021 (2)	0.9806 (2)	0.0486 (12)
H42A	0.7316	0.2814	0.9351	0.058*
H42B	0.7738	0.3395	0.9615	0.058*
C43	0.7039 (2)	0.3215 (2)	1.0394 (3)	0.0498 (12)
H43A	0.6841	0.2835	1.0603	0.060*
H43B	0.6716	0.3463	1.0118	0.060*
C44	0.7299 (2)	0.3599 (2)	1.1077 (3)	0.0538 (13)
H44A	0.6968	0.3700	1.1436	0.081*
H44B	0.7478	0.3986	1.0878	0.081*
H44C	0.7618	0.3357	1.1356	0.081*
C45	0.88471 (18)	0.28197 (17)	0.9297 (2)	0.0300 (9)
H45A	0.9123	0.2625	0.8913	0.036*
H45B	0.8569	0.3107	0.9005	0.036*
C46	0.9237 (2)	0.32022 (19)	0.9862 (2)	0.0366 (10)
H46A	0.9563	0.2936	1.0099	0.044*
H46B	0.8977	0.3360	1.0288	0.044*
C47	0.95265 (19)	0.37462 (18)	0.9443 (2)	0.0349 (10)
H47A	0.9201	0.4044	0.9276	0.042*
H47B	0.9729	0.3591	0.8967	0.042*
C48	0.9997 (2)	0.4083 (2)	0.9957 (3)	0.0528 (13)
H48A	1.0175	0.4430	0.9664	0.079*
H48B	1.0324	0.3791	1.0117	0.079*
H48C	0.9796	0.4246	1.0422	0.079*
C49	0.95509 (19)	0.5494 (2)	0.7532 (3)	0.0431 (11)
H49A	0.9784	0.5720	0.7129	0.052*
H49B	0.9641	0.5699	0.8041	0.052*
C50	0.9787 (2)	0.4832 (2)	0.7574 (3)	0.0553 (13)
H50A	0.9716	0.4612	0.7071	0.066*
H50B	0.9585	0.4596	0.7995	0.066*
C51	1.0508 (3)	0.4912 (4)	0.7762 (5)	0.131 (3)
H51A	1.0689	0.5207	0.7385	0.158*
H51B	1.0571	0.5085	0.8295	0.158*
C52	1.0826 (6)	0.4271 (4)	0.7703 (8)	0.260 (7)
H52A	1.1266	0.4317	0.7827	0.391*
H52B	1.0772	0.4109	0.7169	0.391*
H52C	1.0642	0.3980	0.8074	0.391*
C53	0.8712 (2)	0.62668 (17)	0.7364 (2)	0.0347 (10)
H53A	0.8259	0.6313	0.7334	0.042*
H53B	0.8855	0.6437	0.7875	0.042*
C54	0.8987 (2)	0.66594 (19)	0.6720 (2)	0.0378 (11)
H54A	0.9436	0.6583	0.6704	0.045*
H54B	0.8803	0.6535	0.6208	0.045*
C55	0.8870 (2)	0.73481 (18)	0.6858 (2)	0.0383 (11)
H55A	0.9029	0.7465	0.7386	0.046*
H55B	0.8421	0.7428	0.6841	0.046*
C56	0.9178 (2)	0.7749 (2)	0.6248 (2)	0.0505 (13)
H56A	0.9091	0.8191	0.6349	0.076*
H56B	0.9018	0.7636	0.5726	0.076*
H56C	0.9624	0.7679	0.6274	0.076*
C57	0.84721 (19)	0.52387 (19)	0.7934 (2)	0.0395 (11)
H57A	0.8509	0.4783	0.7850	0.047*
H57B	0.8037	0.5354	0.7827	0.047*
C58	0.8625 (2)	0.53777 (19)	0.8791 (2)	0.0385 (11)
H58A	0.9044	0.5224	0.8925	0.046*
H58B	0.8618	0.5835	0.8879	0.046*
C59	0.8165 (2)	0.5066 (2)	0.9315 (3)	0.0489 (12)
H59A	0.7757	0.5265	0.9230	0.059*
H59B	0.8125	0.4621	0.9164	0.059*
C60	0.8339 (2)	0.5105 (2)	1.0165 (3)	0.0586 (14)
H60A	0.8021	0.4901	1.0474	0.088*
H60B	0.8374	0.5544	1.0321	0.088*
H60C	0.8734	0.4894	1.0258	0.088*
C61	0.87324 (19)	0.5292 (2)	0.6546 (2)	0.0379 (10)
H61A	0.9032	0.5467	0.6176	0.045*
H61B	0.8809	0.4836	0.6577	0.045*
C62	0.8096 (2)	0.5389 (2)	0.6201 (3)	0.0450 (12)
H62A	0.7999	0.5841	0.6193	0.054*
H62B	0.7791	0.5177	0.6531	0.054*
C63	0.8053 (3)	0.5132 (3)	0.5381 (3)	0.0737 (17)
H63A	0.8396	0.5306	0.5077	0.088*
H63B	0.8108	0.4674	0.5405	0.088*
C64	0.7475 (3)	0.5266 (3)	0.4960 (4)	0.099 (2)
H64A	0.7481	0.5073	0.4440	0.148*
H64B	0.7425	0.5719	0.4905	0.148*
H64C	0.7130	0.5096	0.5253	0.148*
N1	0.40682 (14)	−0.07610 (14)	0.73612 (17)	0.0275 (8)
N2	0.33247 (15)	0.26669 (15)	0.96323 (17)	0.0310 (8)
N3	0.84603 (15)	0.23086 (15)	0.96534 (17)	0.0317 (8)
N4	0.88676 (15)	0.55688 (15)	0.73414 (18)	0.0341 (8)
O1	0.46562 (13)	0.31004 (13)	0.65551 (15)	0.0416 (7)
O2	0.42325 (14)	0.35186 (15)	0.77404 (16)	0.0502 (9)
O3	0.35910 (12)	0.29095 (13)	0.68493 (15)	0.0370 (7)
O4	0.43959 (14)	0.24244 (17)	0.76360 (18)	0.0481 (9)
O5	0.77752 (16)	0.37005 (15)	0.65121 (17)	0.0599 (10)
O6	0.87326 (13)	0.36106 (13)	0.7231 (2)	0.0554 (9)
O7	0.77840 (14)	0.37905 (14)	0.79042 (17)	0.0504 (8)
O8	0.79698 (14)	0.27978 (13)	0.73198 (18)	0.0420 (8)
O9	0.38225 (13)	0.14355 (13)	0.70379 (19)	0.0497 (9)
O10	0.29069 (14)	0.19980 (14)	0.73824 (17)	0.0353 (7)
O11	0.28603 (16)	0.11822 (13)	0.64019 (16)	0.0515 (9)
O12	0.30184 (15)	0.09381 (14)	0.77591 (16)	0.0495 (8)
O13	0.88564 (13)	0.21114 (13)	0.67889 (16)	0.0440 (8)
O14	0.99486 (15)	0.18891 (16)	0.66692 (17)	0.0600 (10)
O15	0.96209 (18)	0.28067 (17)	0.7346 (3)	0.0738 (13)
O16	0.94674 (14)	0.18002 (16)	0.79156 (16)	0.0536 (9)
S1	0.42153 (5)	0.30311 (5)	0.71603 (5)	0.0329 (3)
S2	0.80648 (5)	0.35138 (5)	0.72366 (6)	0.0319 (3)
S3	0.31670 (5)	0.13464 (4)	0.71319 (6)	0.0303 (3)
S4	0.94748 (5)	0.21101 (5)	0.71757 (6)	0.0385 (3)
H10	0.3125 (18)	0.2246 (18)	0.719 (2)	0.027 (13)*
H4	0.425 (3)	0.211 (3)	0.742 (3)	0.09 (2)*
H8	0.829 (3)	0.260 (3)	0.707 (4)	0.14 (3)*
H15	0.931 (4)	0.303 (4)	0.732 (5)	0.17 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.028 (2)	0.030 (2)	0.042 (2)	0.0076 (18)	−0.0073 (19)	0.000 (2)
C2	0.042 (3)	0.039 (3)	0.038 (2)	0.008 (2)	−0.005 (2)	0.004 (2)
C3	0.077 (4)	0.052 (3)	0.037 (3)	0.025 (3)	−0.008 (3)	−0.002 (2)
C4	0.103 (5)	0.055 (3)	0.042 (3)	0.026 (3)	−0.008 (3)	0.005 (2)
C5	0.035 (2)	0.025 (2)	0.038 (2)	0.0023 (18)	−0.0055 (19)	−0.0019 (19)
C6	0.045 (3)	0.032 (3)	0.077 (3)	0.001 (2)	−0.024 (3)	−0.014 (2)
C7	0.062 (3)	0.033 (3)	0.057 (3)	−0.004 (2)	−0.008 (3)	−0.013 (2)
C8	0.086 (4)	0.037 (3)	0.083 (4)	−0.011 (3)	−0.002 (3)	0.008 (3)
C9	0.027 (2)	0.034 (2)	0.032 (2)	−0.0009 (18)	0.0002 (18)	−0.0014 (19)
C10	0.039 (3)	0.029 (2)	0.053 (3)	−0.008 (2)	0.001 (2)	−0.004 (2)
C11	0.038 (3)	0.075 (4)	0.138 (6)	−0.003 (3)	0.007 (4)	−0.024 (4)
C12	0.090 (4)	0.089 (4)	0.194 (5)	−0.017 (3)	0.009 (4)	−0.029 (4)
C13	0.031 (2)	0.033 (2)	0.044 (3)	−0.0020 (19)	0.010 (2)	−0.003 (2)
C14	0.056 (3)	0.080 (4)	0.036 (3)	0.013 (3)	0.006 (2)	0.004 (3)
C15	0.077 (4)	0.068 (4)	0.054 (3)	−0.006 (3)	0.013 (3)	0.006 (3)
C16	0.087 (4)	0.083 (4)	0.047 (3)	−0.002 (3)	0.001 (3)	0.022 (3)
C17	0.042 (3)	0.036 (2)	0.021 (2)	−0.004 (2)	−0.0004 (18)	0.0033 (19)
C18	0.065 (3)	0.037 (3)	0.028 (2)	−0.002 (2)	0.003 (2)	−0.001 (2)
C19	0.073 (4)	0.044 (3)	0.046 (3)	0.004 (3)	0.003 (3)	0.004 (2)
C20	0.080 (4)	0.066 (4)	0.055 (3)	0.009 (3)	−0.024 (3)	0.008 (3)
C21	0.035 (2)	0.035 (2)	0.0181 (19)	−0.0015 (19)	0.0018 (17)	0.0007 (18)
C22	0.032 (2)	0.041 (3)	0.037 (2)	−0.004 (2)	−0.004 (2)	0.003 (2)
C23	0.050 (3)	0.105 (5)	0.042 (3)	−0.029 (3)	−0.005 (3)	0.012 (3)
C24	0.057 (4)	0.192 (8)	0.054 (4)	−0.031 (4)	0.023 (3)	−0.049 (4)
C25	0.041 (3)	0.049 (3)	0.024 (2)	0.011 (2)	−0.0014 (19)	−0.008 (2)
C26	0.053 (3)	0.049 (3)	0.033 (2)	0.016 (2)	−0.009 (2)	−0.011 (2)
C27	0.052 (3)	0.073 (4)	0.047 (3)	0.030 (3)	−0.013 (2)	−0.018 (3)
C28	0.081 (4)	0.058 (3)	0.073 (4)	0.030 (3)	−0.036 (3)	−0.022 (3)
C29	0.044 (3)	0.065 (3)	0.022 (2)	−0.029 (2)	−0.003 (2)	−0.007 (2)
C30	0.071 (3)	0.125 (4)	0.051 (3)	−0.046 (3)	−0.002 (3)	−0.004 (3)
C31	0.064 (4)	0.075 (5)	0.169 (7)	−0.015 (4)	0.040 (5)	0.020 (5)
C32	0.090 (5)	0.074 (5)	0.196 (8)	0.012 (4)	0.033 (5)	0.057 (5)
C33	0.040 (3)	0.043 (3)	0.029 (2)	−0.006 (2)	−0.0093 (19)	0.003 (2)
C34	0.060 (3)	0.054 (3)	0.044 (3)	−0.023 (3)	−0.017 (2)	0.010 (2)
C35	0.066 (4)	0.049 (3)	0.060 (3)	−0.016 (3)	−0.020 (3)	0.000 (3)
C36	0.106 (5)	0.067 (4)	0.081 (4)	−0.013 (4)	−0.018 (4)	−0.011 (3)
C37	0.044 (3)	0.039 (2)	0.031 (2)	−0.002 (2)	−0.013 (2)	0.012 (2)
C38	0.051 (3)	0.041 (3)	0.052 (3)	0.007 (2)	−0.005 (2)	0.013 (2)
C39	0.066 (4)	0.073 (4)	0.082 (4)	0.036 (3)	0.009 (3)	0.022 (3)
C40	0.154 (8)	0.128 (7)	0.125 (7)	0.009 (6)	0.022 (6)	0.041 (6)
C41	0.028 (2)	0.047 (3)	0.025 (2)	−0.008 (2)	−0.0020 (18)	0.0025 (19)
C42	0.036 (3)	0.071 (3)	0.039 (3)	0.006 (2)	−0.005 (2)	0.007 (2)
C43	0.046 (3)	0.060 (3)	0.044 (3)	0.005 (2)	−0.001 (2)	0.001 (2)
C44	0.053 (3)	0.051 (3)	0.057 (3)	0.006 (2)	−0.004 (3)	0.003 (3)
C45	0.031 (2)	0.032 (2)	0.026 (2)	−0.0013 (18)	−0.0020 (18)	0.0059 (18)
C46	0.037 (3)	0.039 (2)	0.033 (2)	−0.003 (2)	−0.004 (2)	0.001 (2)
C47	0.032 (2)	0.027 (2)	0.046 (3)	0.0013 (19)	0.007 (2)	0.002 (2)
C48	0.055 (3)	0.038 (3)	0.066 (3)	−0.010 (2)	0.004 (3)	−0.005 (2)
C49	0.027 (2)	0.059 (3)	0.043 (3)	−0.008 (2)	0.000 (2)	0.003 (2)
C50	0.035 (3)	0.071 (4)	0.059 (3)	0.011 (3)	−0.002 (2)	0.011 (3)
C51	0.115 (7)	0.121 (6)	0.157 (7)	0.074 (5)	−0.019 (6)	−0.004 (6)
C52	0.256 (8)	0.265 (8)	0.259 (8)	−0.005 (5)	0.005 (5)	0.011 (5)
C53	0.036 (2)	0.030 (2)	0.037 (2)	−0.0055 (19)	0.003 (2)	−0.003 (2)
C54	0.044 (3)	0.039 (3)	0.031 (2)	−0.014 (2)	−0.001 (2)	−0.001 (2)
C55	0.049 (3)	0.031 (2)	0.034 (2)	−0.008 (2)	−0.006 (2)	0.004 (2)
C56	0.049 (3)	0.056 (3)	0.046 (3)	−0.017 (2)	−0.006 (2)	0.011 (2)
C57	0.030 (2)	0.032 (2)	0.057 (3)	−0.007 (2)	0.005 (2)	0.001 (2)
C58	0.036 (3)	0.035 (2)	0.045 (3)	−0.005 (2)	0.008 (2)	0.000 (2)
C59	0.042 (3)	0.044 (3)	0.061 (3)	0.005 (2)	0.014 (2)	0.015 (2)
C60	0.069 (4)	0.053 (3)	0.055 (3)	0.003 (3)	0.025 (3)	0.006 (3)
C61	0.039 (3)	0.036 (2)	0.039 (2)	−0.003 (2)	0.004 (2)	−0.008 (2)
C62	0.039 (3)	0.038 (3)	0.057 (3)	−0.002 (2)	−0.011 (2)	−0.007 (2)
C63	0.068 (4)	0.066 (4)	0.085 (4)	0.023 (3)	−0.036 (3)	−0.037 (3)
C64	0.094 (5)	0.079 (4)	0.122 (5)	0.012 (4)	−0.044 (4)	−0.034 (4)
N1	0.0242 (18)	0.0268 (18)	0.0314 (18)	0.0014 (14)	−0.0020 (15)	−0.0033 (15)
N2	0.0323 (19)	0.039 (2)	0.0215 (17)	−0.0063 (16)	0.0001 (15)	−0.0057 (15)
N3	0.035 (2)	0.0341 (19)	0.0252 (17)	−0.0015 (16)	−0.0086 (15)	0.0056 (15)
N4	0.031 (2)	0.035 (2)	0.0364 (19)	−0.0067 (16)	−0.0001 (16)	−0.0004 (16)
O1	0.0393 (18)	0.0586 (19)	0.0270 (15)	−0.0124 (15)	0.0009 (13)	0.0043 (14)
O2	0.051 (2)	0.064 (2)	0.0365 (17)	−0.0243 (17)	0.0075 (15)	−0.0139 (16)
O3	0.0344 (17)	0.0422 (17)	0.0339 (15)	−0.0076 (13)	−0.0091 (13)	0.0040 (13)
O4	0.039 (2)	0.061 (2)	0.0435 (19)	−0.0100 (17)	−0.0150 (15)	0.0158 (18)
O5	0.079 (3)	0.059 (2)	0.0414 (18)	0.0268 (18)	−0.0095 (17)	0.0108 (16)
O6	0.0302 (18)	0.0375 (18)	0.099 (3)	−0.0010 (14)	0.0083 (17)	−0.0082 (18)
O7	0.055 (2)	0.0495 (19)	0.0473 (19)	−0.0044 (16)	0.0143 (16)	−0.0154 (16)
O8	0.0354 (18)	0.0334 (17)	0.057 (2)	−0.0021 (14)	0.0001 (16)	0.0070 (15)
O9	0.0313 (18)	0.0367 (17)	0.082 (2)	0.0068 (14)	0.0135 (17)	0.0110 (16)
O10	0.0296 (17)	0.0346 (18)	0.0418 (18)	−0.0051 (15)	0.0053 (14)	−0.0055 (15)
O11	0.082 (3)	0.0378 (18)	0.0341 (17)	−0.0011 (17)	−0.0116 (17)	−0.0062 (14)
O12	0.059 (2)	0.0463 (19)	0.0432 (18)	−0.0079 (16)	0.0023 (16)	0.0160 (15)
O13	0.0407 (18)	0.0519 (19)	0.0385 (16)	0.0094 (15)	−0.0156 (14)	−0.0073 (15)
O14	0.047 (2)	0.095 (3)	0.0373 (17)	0.0261 (19)	0.0006 (15)	−0.0036 (18)
O15	0.051 (2)	0.046 (2)	0.124 (3)	0.0080 (18)	−0.038 (2)	−0.008 (2)
O16	0.048 (2)	0.078 (2)	0.0337 (17)	0.0190 (17)	−0.0043 (15)	0.0084 (17)
S1	0.0331 (6)	0.0443 (7)	0.0211 (5)	−0.0134 (5)	−0.0027 (4)	0.0007 (5)
S2	0.0334 (6)	0.0292 (6)	0.0333 (6)	0.0028 (5)	0.0017 (5)	−0.0006 (5)
S3	0.0357 (6)	0.0263 (5)	0.0289 (6)	−0.0010 (5)	0.0019 (5)	0.0028 (5)
S4	0.0389 (7)	0.0422 (7)	0.0340 (6)	0.0144 (5)	−0.0066 (5)	−0.0030 (5)

Geometric parameters (Å, º) top

C1—N1	1.515 (5)	C41—C42	1.508 (6)
C1—C2	1.531 (5)	C41—N3	1.520 (5)
C2—C3	1.522 (6)	C42—C43	1.525 (6)
C3—C4	1.533 (6)	C43—C44	1.525 (6)
C5—N1	1.513 (5)	C45—C46	1.510 (5)
C5—C6	1.519 (6)	C45—N3	1.515 (5)
C6—C7	1.531 (6)	C46—C47	1.512 (5)
C7—C8	1.478 (6)	C47—C48	1.515 (6)
C9—N1	1.510 (5)	C49—C50	1.508 (6)
C9—C10	1.524 (5)	C49—N4	1.521 (5)
C10—C12	1.440 (8)	C50—C51	1.601 (9)
C11—C12	1.348 (8)	C51—C52	1.540 (13)
C13—N1	1.521 (5)	C53—C54	1.518 (5)
C13—C14	1.526 (6)	C53—N4	1.532 (5)
C14—C15	1.463 (6)	C54—C55	1.515 (6)
C15—C16	1.500 (7)	C55—C56	1.519 (6)
C17—C18	1.510 (6)	C57—N4	1.517 (5)
C17—N2	1.524 (5)	C57—C58	1.525 (6)
C18—C19	1.543 (6)	C58—C59	1.512 (6)
C19—C20	1.506 (6)	C59—C60	1.494 (6)
C21—C22	1.511 (5)	C61—C62	1.504 (6)
C21—N2	1.515 (5)	C61—N4	1.506 (5)
C22—C23	1.518 (6)	C62—C63	1.507 (6)
C23—C24	1.504 (8)	C63—C64	1.461 (7)
C25—N2	1.512 (5)	O1—S1	1.434 (3)
C25—C26	1.518 (6)	O2—S1	1.439 (3)
C26—C27	1.516 (6)	O3—S1	1.469 (3)
C27—C28	1.505 (6)	O4—S1	1.577 (3)
C29—C30	1.515 (6)	O5—S2	1.433 (3)
C29—N2	1.516 (5)	O6—S2	1.466 (3)
C30—C31	1.658 (8)	O7—S2	1.434 (3)
C31—C32	1.387 (8)	O8—S2	1.553 (3)
C33—C34	1.498 (6)	O9—S3	1.450 (3)
C33—N3	1.525 (5)	O10—S3	1.568 (3)
C34—C35	1.533 (6)	O11—S3	1.444 (3)
C35—C36	1.479 (7)	O12—S3	1.426 (3)
C37—C38	1.503 (6)	O13—S4	1.484 (3)
C37—N3	1.526 (5)	O14—S4	1.440 (3)
C38—C39	1.527 (6)	O15—S4	1.551 (4)
C39—C40	1.398 (9)	O16—S4	1.428 (3)

N1—C1—C2	114.5 (3)	C9—N1—C5	105.8 (3)
C3—C2—C1	110.5 (4)	C9—N1—C1	111.7 (3)
C2—C3—C4	110.3 (4)	C5—N1—C1	111.3 (3)
N1—C5—C6	115.5 (3)	C9—N1—C13	110.8 (3)
C5—C6—C7	110.8 (4)	C5—N1—C13	110.6 (3)
C8—C7—C6	113.7 (4)	C1—N1—C13	106.7 (3)
N1—C9—C10	115.3 (3)	C25—N2—C21	111.9 (3)
C12—C10—C9	113.5 (4)	C25—N2—C29	110.8 (3)
C11—C12—C10	135.6 (6)	C21—N2—C29	105.0 (3)
N1—C13—C14	114.6 (3)	C25—N2—C17	105.3 (3)
C15—C14—C13	114.8 (4)	C21—N2—C17	112.0 (3)
C14—C15—C16	114.1 (5)	C29—N2—C17	111.9 (3)
C18—C17—N2	115.6 (3)	C45—N3—C41	111.4 (3)
C17—C18—C19	109.8 (3)	C45—N3—C33	105.8 (3)
C20—C19—C18	114.0 (4)	C41—N3—C33	112.2 (3)
C22—C21—N2	115.6 (3)	C45—N3—C37	111.9 (3)
C21—C22—C23	110.6 (3)	C41—N3—C37	105.0 (3)
C24—C23—C22	113.7 (5)	C33—N3—C37	110.6 (3)
N2—C25—C26	115.1 (3)	C61—N4—C57	108.5 (3)
C27—C26—C25	110.5 (3)	C61—N4—C49	108.7 (3)
C28—C27—C26	111.0 (4)	C57—N4—C49	111.9 (3)
C30—C29—N2	115.5 (3)	C61—N4—C53	111.6 (3)
C29—C30—C31	107.1 (4)	C57—N4—C53	108.0 (3)
C32—C31—C30	97.6 (6)	C49—N4—C53	108.2 (3)
C34—C33—N3	116.3 (3)	O1—S1—O2	114.50 (17)
C33—C34—C35	111.0 (4)	O1—S1—O3	112.60 (16)
C36—C35—C34	113.7 (5)	O2—S1—O3	112.75 (18)
C38—C37—N3	116.1 (3)	O1—S1—O4	107.14 (18)
C37—C38—C39	107.6 (4)	O2—S1—O4	103.87 (19)
C40—C39—C38	115.9 (6)	O3—S1—O4	104.93 (17)
C42—C41—N3	115.9 (3)	O5—S2—O7	112.69 (19)
C41—C42—C43	110.0 (3)	O5—S2—O6	111.7 (2)
C42—C43—C44	113.8 (4)	O7—S2—O6	112.7 (2)
C46—C45—N3	116.3 (3)	O5—S2—O8	107.31 (19)
C45—C46—C47	110.4 (3)	O7—S2—O8	105.94 (18)
C46—C47—C48	112.0 (3)	O6—S2—O8	105.89 (17)
C50—C49—N4	116.0 (4)	O12—S3—O11	113.09 (18)
C49—C50—C51	103.9 (4)	O12—S3—O9	113.83 (19)
C52—C51—C50	109.3 (8)	O11—S3—O9	111.8 (2)
C54—C53—N4	115.5 (3)	O12—S3—O10	104.51 (18)
C55—C54—C53	110.8 (3)	O11—S3—O10	106.87 (17)
C54—C55—C56	111.3 (4)	O9—S3—O10	105.94 (17)
N4—C57—C58	115.9 (3)	O16—S4—O14	113.73 (19)
C59—C58—C57	110.5 (4)	O16—S4—O13	111.51 (19)
C60—C59—C58	113.3 (4)	O14—S4—O13	112.68 (18)
C62—C61—N4	117.2 (3)	O16—S4—O15	106.7 (2)
C61—C62—C63	110.6 (4)	O14—S4—O15	106.4 (2)
C64—C63—C62	114.9 (5)	O13—S4—O15	105.14 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O3	0.79 (4)	1.85 (4)	2.628 (4)	171 (4)
O4—H4···O9	0.84 (6)	1.82 (6)	2.649 (5)	171 (6)
O8—H8···O13	0.92 (7)	1.70 (7)	2.602 (4)	166 (7)
O15—H15···O6	0.82 (8)	1.78 (8)	2.590 (5)	170 (9)

Experimental details

Crystal data
Chemical formula	C₁₆H₃₆N⁺·HSO₄⁻
M_r	339.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	21.7299 (4), 21.3998 (4), 17.0880 (4)
β (°)	91.318 (3)
V (Å³)	7944.1 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.982, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	38718, 13981, 8004
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.237, 1.02
No. of reflections	13981
No. of parameters	809
No. of restraints	19
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.26, −0.70

Computer programs: COLLECT (Hooft, 1998), SCALEPACK (Otwinoski & Minor, 1997) and COLLECT, DENZO, COLLECT maXus (Mackay et al., 1998), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), CAMERON (Watkin et al., 1993), WinGX (Farrugia, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10···O3	0.79 (4)	1.85 (4)	2.628 (4)	171 (4)
O4—H4···O9	0.84 (6)	1.82 (6)	2.649 (5)	171 (6)
O8—H8···O13	0.92 (7)	1.70 (7)	2.602 (4)	166 (7)
O15—H15···O6	0.82 (8)	1.78 (8)	2.590 (5)	170 (9)

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Anion-anion dimerization in tetra­butyl­ammonium hydrogen­sulfate