Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011321/bt6059sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011321/bt6059Isup2.hkl |
CCDC reference: 170897
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
There is some thermal disorder in ends of the tetrabutylammonium groups, but it was not found possible to model it with split sites. This results in several long and short C—C bonds. The hydroxyl H atoms were refined isotropically.
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).
C16H36N+·HSO4− | F(000) = 3008 |
Mr = 339.53 | Dx = 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 |
Nonius KappaCCD area-detector diffractometer | 13981 independent reflections |
Radiation source: Nonius FR591 rotating anode | 8004 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 9.091 pixels mm1 pixels mm-1 | θmax = 25.0°, θmin = 2.9° |
ϕ and ω scans to fill the Ewald sphere | h = −25→25 |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | k = −25→24 |
Tmin = 0.982, Tmax = 0.982 | l = −20→20 |
38718 measured reflections |
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(Fo2) + (0.1368P)2 + 1.0999P] where P = (Fo2 + 2Fc2)/3 |
13981 reflections | (Δ/σ)max < 0.001 |
809 parameters | Δρmax = 1.26 e Å−3 |
19 restraints | Δρmin = −0.70 e Å−3 |
C16H36N+·HSO4− | V = 7944.1 (3) Å3 |
Mr = 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)° |
Nonius KappaCCD area-detector diffractometer | 13981 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 8004 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.982 | Rint = 0.068 |
38718 measured reflections |
R[F2 > 2σ(F2)] = 0.074 | 19 restraints |
wR(F2) = 0.237 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.26 e Å−3 |
13981 reflections | Δρmin = −0.70 e Å−3 |
809 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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)* |
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) |
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) |
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− |
Mr | 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) |
Tmin, Tmax | 0.982, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38718, 13981, 8004 |
Rint | 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 |
Δρmax, Δρmin (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).
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) |
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.