Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049471/ci2477sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049471/ci2477Isup2.hkl |
CCDC reference: 667363
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.050
- wR factor = 0.150
- Data-to-parameter ratio = 22.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.14 Ratio PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 16
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Compound (I) was synthesized by adding CS2 (2.4 ml, 40 mmol) to a solution of salicylic acid hydrazide (3.04 g, 20 mmol) in ethanol (15 ml) in the presence of KOH (1.12 g, 20 mmol) and stirring the reaction mixture for 2 h at room temperature. The solid product obtained in the above reaction was dissolved in EtOH-H2O mixture (75:25 v/v) and an EtOH solution of tetrabutylammonium bromide (3.22 g, 10 mmol) was added. The resulting dirty yellow solution was concentrated at room temperature to obtain solid of compound (I). The solid product was dissolved in minimum amount of ethanol (20 ml), to which water was added drop wise whereupon the impurity settled out. The solution was decanted and after evaporation of the solvent compound (I) solidified. White single crystals of (I) (m.p. 347 K) suitable for X-ray analysis were obtained by slow evaporation of a methanol solution over a period of 5 d. (yield 2.90 g, 68.75%): Analysis calculated: C 66.16, H 9.48, N 9.64%; found for C24H41N3O2S (435.66): C 66.10, H 9.43, N 9.68%; IR (KBr, ν cm-1): 3441 (OH), 1288 (C—O), 1601 (C=N), 1070 (N—N), 902 (C—S); 13C NMR (CDCl3, TMS): 179.78 (C1A), 160.81 (C2A), 124.71 (C3A), 160.25 (C4A), 133.35 (C5A), 129.33 (C6A), 118.10 (C7A), 128.91 (C8A), 57.52 (C11A, C21A, C31A, C41A), 23.04 (C12A, C22A, C32A, C32B, C42A), 19.16 (C13A, C23A, C33A, C43A), 13.42 (C14A, C24A, C34A, C44A).
All H atoms were initially located in a difference Fourier map. C-bound H atoms were then constrained to an ideal geometry with C—H distances in the range of 0.95–0.99 Å and Uiso(H) = 1.2Ueq(C). O-bound H atoms were refined freely. One of the n-butyl arms of one of the two tetrabutylammonium cations is disordered over two conformations with occupancies of 0.641 (7) and 0.359 (7). Both conformers were constrained to have similar geometries.
The title compound was synthesized by the ring closure reaction of the product obtained by the reaction of carbon disulfide with salicylic acid hydrazide in the presence of a base, followed by the addition of tetrabutylammoniumbromide in ethanolic medium.
The compound crystallizes in the monoclinic space group P21/n with two formula units in the asymmetric unit. The contents of the asymmetric unit, together with the atom-labelling scheme, are shown in Fig 1. The bond lengths and angles of the 1,3,4-oxadiazole ring are in good agreement with the values quoted in previous reports (Zhang et al., 2002; Singh et al. 2006, 2007; Stockhouse et al. 2001; Du & Zhao, 2004). The C1A—N1A [1.312 (3) Å] and C1B—N1B [1.308 (3) Å] bond lengths are intermediate between 1.47 Å for a C—N single bond and 1.29 Å for a C═ N double bond, and are significantly longer than the C2A—N2A [1.287 (3) Å] and C2B—N2B [1.290 (3) Å] bond lengths. The C—S bond distances [S1A—C1A = 1.674 (3) Å and S1B—C1B [1.684 (2) Å] are also intermediate between 1.82 Å for a C—S single bond and 1.56 Å for a C═S double bond.
In both molecules, the oxadiazole ring is almost coplanar with the 2-hydroxyphenyl ring. The dihedral angle between the two rings is 6.6 (1)° for molecule A and 1.4 (1)° for molecule B.
The molecular structure of each independent anion is influenced by O2A–H2A···N2A or O2B–H2B···N2B intramolecular hydrogen bonding. In the crystal structure, weak intermolecular C—H···S, C—H···N, and C—H···O interactions are observed (Table 1). In addition, the crystal packing is reinforced by weak intermolecular C—H···π interactions involving the C42A—H42B bond and the O1B/C1B/N1B/N2B/C2B ring [H···ring centroid = 2.92 Å, C21B···ring centroid = 3.578 (3) Å]. Thus the planarity of the two rings, π-electron delocalization, intermolecular and intramolecular interactions all contribute to stabilize the structure of the compound.
For related structures, see: Du & Zhao (2004); Singh et al. (2006); Singh et al. (2007); Stockhouse et al. (2001); Zhang et al. (2002).
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C16H36N+·C8H5N2O2S− | F(000) = 1904 |
Mr = 435.66 | Dx = 1.110 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7605 reflections |
a = 16.600 (6) Å | θ = 2.2–24.2° |
b = 13.228 (5) Å | µ = 0.15 mm−1 |
c = 23.957 (9) Å | T = 173 K |
β = 97.710 (6)° | Plate, colorless |
V = 5213 (3) Å3 | 0.51 × 0.43 × 0.23 mm |
Z = 8 |
Bruker APEXII CCD area-detector diffractometer | 12911 independent reflections |
Radiation source: fine-focus sealed tube | 5952 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 28.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −21→22 |
Tmin = 0.929, Tmax = 0.967 | k = −17→17 |
51583 measured reflections | l = −32→29 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0458P)2 + 2.3996P] where P = (Fo2 + 2Fc2)/3 |
12911 reflections | (Δ/σ)max = 0.001 |
586 parameters | Δρmax = 0.22 e Å−3 |
16 restraints | Δρmin = −0.31 e Å−3 |
C16H36N+·C8H5N2O2S− | V = 5213 (3) Å3 |
Mr = 435.66 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.600 (6) Å | µ = 0.15 mm−1 |
b = 13.228 (5) Å | T = 173 K |
c = 23.957 (9) Å | 0.51 × 0.43 × 0.23 mm |
β = 97.710 (6)° |
Bruker APEXII CCD area-detector diffractometer | 12911 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 5952 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.967 | Rint = 0.081 |
51583 measured reflections |
R[F2 > 2σ(F2)] = 0.050 | 16 restraints |
wR(F2) = 0.150 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.22 e Å−3 |
12911 reflections | Δρmin = −0.31 e Å−3 |
586 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 | Occ. (<1) | |
S1A | 0.37223 (4) | 0.70771 (5) | 0.20112 (3) | 0.0557 (2) | |
O1A | 0.30749 (9) | 0.60789 (11) | 0.10893 (6) | 0.0412 (4) | |
O2A | 0.31975 (14) | 0.31664 (15) | 0.04194 (10) | 0.0702 (6) | |
H2A | 0.3507 (19) | 0.347 (2) | 0.0708 (13) | 0.079 (11)* | |
N1A | 0.39980 (12) | 0.51807 (15) | 0.16416 (9) | 0.0465 (5) | |
N2A | 0.36975 (13) | 0.46067 (15) | 0.11638 (9) | 0.0471 (5) | |
C1A | 0.36270 (14) | 0.60585 (19) | 0.15926 (10) | 0.0416 (6) | |
C2A | 0.31688 (15) | 0.51541 (18) | 0.08591 (10) | 0.0404 (6) | |
C3A | 0.26839 (15) | 0.48733 (19) | 0.03352 (10) | 0.0438 (6) | |
C4A | 0.27140 (17) | 0.3875 (2) | 0.01407 (12) | 0.0529 (7) | |
C5A | 0.22353 (19) | 0.3599 (2) | −0.03591 (13) | 0.0657 (8) | |
H5A | 0.2256 | 0.2926 | −0.0496 | 0.079* | |
C6A | 0.17315 (18) | 0.4302 (3) | −0.06550 (13) | 0.0691 (9) | |
H6A | 0.1405 | 0.4108 | −0.0994 | 0.083* | |
C7A | 0.16958 (18) | 0.5278 (3) | −0.04651 (12) | 0.0664 (9) | |
H7A | 0.1346 | 0.5754 | −0.0672 | 0.080* | |
C8A | 0.21686 (16) | 0.5564 (2) | 0.00271 (11) | 0.0542 (7) | |
H8A | 0.2143 | 0.6240 | 0.0158 | 0.065* | |
S1B | 0.34712 (4) | 0.71102 (5) | 0.67823 (3) | 0.04552 (17) | |
O1B | 0.27317 (9) | 0.60672 (11) | 0.59033 (6) | 0.0396 (4) | |
O2B | 0.31007 (11) | 0.33542 (13) | 0.50700 (8) | 0.0498 (5) | |
H2B | 0.3400 (18) | 0.360 (2) | 0.5362 (12) | 0.071 (10)* | |
N1B | 0.38606 (12) | 0.53313 (14) | 0.63132 (9) | 0.0424 (5) | |
N2B | 0.35079 (12) | 0.47286 (14) | 0.58594 (8) | 0.0416 (5) | |
C1B | 0.33942 (14) | 0.61234 (17) | 0.63338 (10) | 0.0374 (5) | |
C2B | 0.28563 (14) | 0.51866 (17) | 0.56379 (10) | 0.0370 (5) | |
C3B | 0.22823 (15) | 0.48426 (17) | 0.51656 (10) | 0.0390 (6) | |
C4B | 0.24315 (15) | 0.39264 (18) | 0.49015 (10) | 0.0416 (6) | |
C5B | 0.18907 (16) | 0.3588 (2) | 0.44487 (11) | 0.0496 (7) | |
H5B | 0.1994 | 0.2972 | 0.4267 | 0.060* | |
C6B | 0.12055 (18) | 0.4140 (2) | 0.42610 (12) | 0.0571 (7) | |
H6B | 0.0838 | 0.3901 | 0.3951 | 0.069* | |
C7B | 0.10472 (19) | 0.5043 (2) | 0.45203 (12) | 0.0642 (8) | |
H7B | 0.0570 | 0.5417 | 0.4392 | 0.077* | |
C8B | 0.15880 (16) | 0.5394 (2) | 0.49666 (11) | 0.0522 (7) | |
H8B | 0.1485 | 0.6018 | 0.5140 | 0.063* | |
N1 | 0.64839 (11) | 0.57678 (14) | 0.20150 (8) | 0.0375 (5) | |
C11A | 0.63841 (15) | 0.64087 (18) | 0.14823 (10) | 0.0413 (6) | |
H11A | 0.6500 | 0.7121 | 0.1591 | 0.050* | |
H11B | 0.6799 | 0.6194 | 0.1246 | 0.050* | |
C12A | 0.55586 (16) | 0.6366 (2) | 0.11253 (11) | 0.0500 (7) | |
H12A | 0.5450 | 0.5668 | 0.0986 | 0.060* | |
H12B | 0.5131 | 0.6552 | 0.1358 | 0.060* | |
C13A | 0.55304 (18) | 0.7082 (2) | 0.06317 (11) | 0.0634 (8) | |
H13A | 0.6037 | 0.7010 | 0.0460 | 0.076* | |
H13B | 0.5505 | 0.7785 | 0.0770 | 0.076* | |
C14A | 0.4807 (2) | 0.6891 (3) | 0.01852 (13) | 0.0829 (10) | |
H14A | 0.4817 | 0.7374 | −0.0124 | 0.124* | |
H14B | 0.4303 | 0.6976 | 0.0351 | 0.124* | |
H14C | 0.4835 | 0.6201 | 0.0041 | 0.124* | |
C21A | 0.59405 (14) | 0.61311 (17) | 0.24331 (10) | 0.0403 (6) | |
H21A | 0.6053 | 0.5713 | 0.2777 | 0.048* | |
H21B | 0.5369 | 0.6007 | 0.2271 | 0.048* | |
C22A | 0.60217 (16) | 0.72338 (19) | 0.26044 (11) | 0.0482 (6) | |
H22A | 0.5795 | 0.7668 | 0.2285 | 0.058* | |
H22B | 0.6603 | 0.7408 | 0.2706 | 0.058* | |
C23A | 0.55669 (16) | 0.7419 (2) | 0.31053 (11) | 0.0540 (7) | |
H23A | 0.5847 | 0.7058 | 0.3438 | 0.065* | |
H23B | 0.5011 | 0.7139 | 0.3022 | 0.065* | |
C24A | 0.5515 (2) | 0.8540 (2) | 0.32434 (14) | 0.0763 (10) | |
H24A | 0.5218 | 0.8625 | 0.3567 | 0.114* | |
H24B | 0.5228 | 0.8898 | 0.2918 | 0.114* | |
H24C | 0.6064 | 0.8817 | 0.3334 | 0.114* | |
C31A | 0.62430 (14) | 0.46778 (16) | 0.18865 (10) | 0.0396 (6) | |
H31A | 0.5664 | 0.4663 | 0.1721 | 0.047* | |
H31B | 0.6291 | 0.4300 | 0.2246 | 0.047* | |
C32A | 0.67344 (16) | 0.41286 (18) | 0.14902 (11) | 0.0474 (6) | |
H32A | 0.6709 | 0.4507 | 0.1132 | 0.057* | |
H32B | 0.7311 | 0.4090 | 0.1661 | 0.057* | |
C33A | 0.64023 (18) | 0.30731 (19) | 0.13752 (12) | 0.0574 (7) | |
H33A | 0.5832 | 0.3119 | 0.1193 | 0.069* | |
H33B | 0.6405 | 0.2712 | 0.1737 | 0.069* | |
C34A | 0.6894 (2) | 0.2470 (2) | 0.09976 (13) | 0.0681 (9) | |
H34A | 0.6657 | 0.1794 | 0.0935 | 0.102* | |
H34B | 0.7457 | 0.2410 | 0.1179 | 0.102* | |
H34C | 0.6884 | 0.2817 | 0.0635 | 0.102* | |
C41A | 0.73787 (14) | 0.58491 (17) | 0.22524 (10) | 0.0406 (6) | |
H41A | 0.7703 | 0.5604 | 0.1962 | 0.049* | |
H41B | 0.7510 | 0.6574 | 0.2317 | 0.049* | |
C42A | 0.76561 (14) | 0.52838 (18) | 0.27942 (10) | 0.0436 (6) | |
H42A | 0.7463 | 0.4576 | 0.2760 | 0.052* | |
H42B | 0.7424 | 0.5605 | 0.3110 | 0.052* | |
C43A | 0.85770 (15) | 0.5303 (2) | 0.29096 (11) | 0.0505 (7) | |
H43A | 0.8762 | 0.6015 | 0.2941 | 0.061* | |
H43B | 0.8801 | 0.4995 | 0.2587 | 0.061* | |
C44A | 0.89112 (17) | 0.4743 (2) | 0.34442 (12) | 0.0611 (8) | |
H44A | 0.9506 | 0.4780 | 0.3498 | 0.092* | |
H44B | 0.8741 | 0.4034 | 0.3413 | 0.092* | |
H44C | 0.8702 | 0.5054 | 0.3767 | 0.092* | |
N2 | 0.37404 (12) | 0.39697 (14) | 0.33340 (9) | 0.0435 (5) | |
C11B | 0.4069 (10) | 0.4927 (8) | 0.3637 (6) | 0.043 (2) | 0.641 (7) |
H11C | 0.4665 | 0.4849 | 0.3727 | 0.051* | 0.641 (7) |
H11D | 0.3972 | 0.5493 | 0.3366 | 0.051* | 0.641 (7) |
C12B | 0.3747 (8) | 0.5252 (6) | 0.4176 (3) | 0.052 (2) | 0.641 (7) |
H12C | 0.3885 | 0.4726 | 0.4467 | 0.063* | 0.641 (7) |
H12D | 0.3147 | 0.5300 | 0.4102 | 0.063* | 0.641 (7) |
C13B | 0.4091 (5) | 0.6269 (5) | 0.4404 (3) | 0.074 (2) | 0.641 (7) |
H13C | 0.3982 | 0.6349 | 0.4798 | 0.089* | 0.641 (7) |
H13D | 0.4688 | 0.6269 | 0.4406 | 0.089* | 0.641 (7) |
C14B | 0.3731 (5) | 0.7151 (5) | 0.4062 (3) | 0.107 (3) | 0.641 (7) |
H14D | 0.3971 | 0.7781 | 0.4224 | 0.160* | 0.641 (7) |
H14E | 0.3142 | 0.7165 | 0.4066 | 0.160* | 0.641 (7) |
H14F | 0.3846 | 0.7083 | 0.3673 | 0.160* | 0.641 (7) |
C11C | 0.410 (2) | 0.4999 (15) | 0.3510 (12) | 0.050 (5) | 0.359 (7) |
H11E | 0.4692 | 0.4931 | 0.3647 | 0.060* | 0.359 (7) |
H11F | 0.4038 | 0.5470 | 0.3186 | 0.060* | 0.359 (7) |
C12C | 0.3654 (13) | 0.5394 (10) | 0.3978 (5) | 0.050 (3) | 0.359 (7) |
H12E | 0.3743 | 0.4943 | 0.4310 | 0.060* | 0.359 (7) |
H12F | 0.3063 | 0.5432 | 0.3847 | 0.060* | 0.359 (7) |
C13C | 0.3997 (8) | 0.6445 (8) | 0.4127 (4) | 0.059 (3) | 0.359 (7) |
H13E | 0.4592 | 0.6394 | 0.4235 | 0.071* | 0.359 (7) |
H13F | 0.3897 | 0.6884 | 0.3790 | 0.071* | 0.359 (7) |
C14C | 0.3624 (6) | 0.6929 (8) | 0.4603 (4) | 0.083 (4) | 0.359 (7) |
H14G | 0.3865 | 0.7598 | 0.4683 | 0.124* | 0.359 (7) |
H14H | 0.3730 | 0.6504 | 0.4940 | 0.124* | 0.359 (7) |
H14I | 0.3036 | 0.6997 | 0.4495 | 0.124* | 0.359 (7) |
C21B | 0.28409 (14) | 0.40714 (19) | 0.31129 (12) | 0.0487 (7) | |
H21C | 0.2660 | 0.3443 | 0.2909 | 0.058* | |
H21D | 0.2535 | 0.4130 | 0.3439 | 0.058* | |
C22B | 0.26181 (17) | 0.4962 (2) | 0.27233 (14) | 0.0681 (9) | |
H22C | 0.3034 | 0.5043 | 0.2466 | 0.082* | |
H22D | 0.2611 | 0.5588 | 0.2949 | 0.082* | |
C23B | 0.17851 (19) | 0.4807 (3) | 0.23776 (15) | 0.0759 (10) | |
H23C | 0.1396 | 0.4579 | 0.2630 | 0.091* | |
H23D | 0.1588 | 0.5461 | 0.2211 | 0.091* | |
C24D | 0.1803 (2) | 0.4042 (3) | 0.19130 (15) | 0.0870 (11) | |
H24D | 0.1256 | 0.3969 | 0.1704 | 0.130* | |
H24E | 0.1986 | 0.3388 | 0.2076 | 0.130* | |
H24F | 0.2178 | 0.4270 | 0.1656 | 0.130* | |
C31B | 0.38041 (15) | 0.31129 (18) | 0.37581 (11) | 0.0438 (6) | |
H31C | 0.3556 | 0.2502 | 0.3568 | 0.053* | |
H31D | 0.3478 | 0.3293 | 0.4061 | 0.053* | |
C32B | 0.46590 (16) | 0.2847 (2) | 0.40281 (11) | 0.0527 (7) | |
H32C | 0.4897 | 0.3429 | 0.4252 | 0.063* | |
H32D | 0.5003 | 0.2707 | 0.3730 | 0.063* | |
C33B | 0.46514 (18) | 0.1922 (2) | 0.44100 (12) | 0.0591 (8) | |
H33C | 0.5200 | 0.1837 | 0.4625 | 0.071* | |
H33D | 0.4267 | 0.2047 | 0.4685 | 0.071* | |
C34B | 0.4413 (2) | 0.0947 (2) | 0.40990 (14) | 0.0763 (10) | |
H34D | 0.4422 | 0.0391 | 0.4370 | 0.114* | |
H34E | 0.4799 | 0.0804 | 0.3833 | 0.114* | |
H34F | 0.3865 | 0.1015 | 0.3893 | 0.114* | |
C41B | 0.42319 (15) | 0.37380 (18) | 0.28570 (11) | 0.0447 (6) | |
H41C | 0.4168 | 0.4309 | 0.2588 | 0.054* | |
H41D | 0.4813 | 0.3704 | 0.3016 | 0.054* | |
C42B | 0.40114 (17) | 0.2770 (2) | 0.25339 (12) | 0.0578 (7) | |
H42C | 0.4079 | 0.2186 | 0.2795 | 0.069* | |
H42D | 0.3435 | 0.2796 | 0.2361 | 0.069* | |
C43B | 0.45533 (17) | 0.2639 (2) | 0.20792 (11) | 0.0533 (7) | |
H43C | 0.4516 | 0.3254 | 0.1842 | 0.064* | |
H43D | 0.5124 | 0.2573 | 0.2259 | 0.064* | |
C44B | 0.4340 (2) | 0.1731 (3) | 0.17077 (14) | 0.0787 (10) | |
H44D | 0.4712 | 0.1691 | 0.1424 | 0.118* | |
H44E | 0.3780 | 0.1797 | 0.1520 | 0.118* | |
H44F | 0.4388 | 0.1117 | 0.1938 | 0.118* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0585 (4) | 0.0526 (4) | 0.0529 (4) | 0.0059 (3) | −0.0040 (3) | −0.0101 (3) |
O1A | 0.0441 (10) | 0.0398 (9) | 0.0383 (9) | 0.0044 (8) | 0.0005 (8) | 0.0001 (8) |
O2A | 0.0852 (16) | 0.0477 (12) | 0.0773 (16) | 0.0024 (11) | 0.0094 (13) | −0.0132 (11) |
N1A | 0.0467 (12) | 0.0457 (12) | 0.0459 (13) | 0.0045 (10) | 0.0019 (10) | 0.0042 (10) |
N2A | 0.0516 (13) | 0.0426 (12) | 0.0471 (13) | 0.0040 (10) | 0.0067 (11) | 0.0010 (10) |
C1A | 0.0400 (14) | 0.0481 (15) | 0.0365 (13) | 0.0001 (11) | 0.0041 (11) | 0.0043 (11) |
C2A | 0.0426 (14) | 0.0386 (13) | 0.0414 (14) | −0.0001 (11) | 0.0102 (12) | 0.0004 (11) |
C3A | 0.0427 (14) | 0.0504 (15) | 0.0404 (14) | −0.0037 (12) | 0.0129 (12) | −0.0027 (12) |
C4A | 0.0529 (17) | 0.0539 (16) | 0.0546 (17) | −0.0054 (14) | 0.0169 (14) | −0.0099 (14) |
C5A | 0.065 (2) | 0.073 (2) | 0.062 (2) | −0.0159 (17) | 0.0195 (17) | −0.0236 (17) |
C6A | 0.0542 (19) | 0.106 (3) | 0.0481 (18) | −0.0170 (19) | 0.0126 (15) | −0.0217 (19) |
C7A | 0.0557 (18) | 0.096 (2) | 0.0457 (17) | 0.0006 (17) | 0.0012 (14) | −0.0049 (17) |
C8A | 0.0514 (16) | 0.0648 (17) | 0.0457 (16) | 0.0025 (14) | 0.0038 (13) | −0.0029 (14) |
S1B | 0.0513 (4) | 0.0428 (3) | 0.0421 (4) | 0.0025 (3) | 0.0049 (3) | −0.0048 (3) |
O1B | 0.0439 (9) | 0.0357 (8) | 0.0380 (9) | 0.0056 (7) | 0.0007 (8) | −0.0002 (7) |
O2B | 0.0505 (11) | 0.0465 (10) | 0.0533 (12) | 0.0046 (9) | 0.0100 (10) | −0.0082 (9) |
N1B | 0.0405 (11) | 0.0397 (11) | 0.0464 (12) | 0.0028 (9) | 0.0041 (10) | 0.0003 (10) |
N2B | 0.0427 (12) | 0.0388 (11) | 0.0430 (12) | 0.0038 (9) | 0.0049 (10) | −0.0010 (9) |
C1B | 0.0381 (13) | 0.0398 (13) | 0.0346 (13) | −0.0010 (11) | 0.0057 (11) | 0.0039 (11) |
C2B | 0.0432 (14) | 0.0340 (12) | 0.0354 (13) | 0.0015 (11) | 0.0114 (11) | 0.0001 (11) |
C3B | 0.0465 (14) | 0.0371 (12) | 0.0341 (13) | −0.0001 (11) | 0.0076 (11) | 0.0038 (11) |
C4B | 0.0482 (15) | 0.0403 (13) | 0.0385 (14) | −0.0020 (12) | 0.0142 (12) | 0.0033 (11) |
C5B | 0.0600 (17) | 0.0452 (14) | 0.0456 (15) | −0.0118 (13) | 0.0139 (14) | −0.0070 (12) |
C6B | 0.0644 (19) | 0.0609 (18) | 0.0440 (16) | −0.0100 (15) | −0.0006 (14) | −0.0033 (14) |
C7B | 0.071 (2) | 0.0609 (18) | 0.0546 (18) | 0.0086 (15) | −0.0146 (16) | 0.0024 (15) |
C8B | 0.0615 (17) | 0.0459 (15) | 0.0462 (16) | 0.0075 (13) | −0.0043 (14) | −0.0007 (12) |
N1 | 0.0410 (11) | 0.0337 (10) | 0.0383 (11) | −0.0015 (9) | 0.0069 (9) | 0.0021 (9) |
C11A | 0.0478 (15) | 0.0391 (13) | 0.0385 (13) | −0.0009 (11) | 0.0112 (12) | 0.0073 (11) |
C12A | 0.0507 (16) | 0.0569 (16) | 0.0424 (15) | 0.0006 (13) | 0.0066 (13) | 0.0110 (13) |
C13A | 0.0642 (19) | 0.078 (2) | 0.0485 (16) | 0.0110 (16) | 0.0103 (15) | 0.0168 (16) |
C14A | 0.086 (2) | 0.100 (3) | 0.059 (2) | 0.019 (2) | −0.0053 (18) | 0.0095 (19) |
C21A | 0.0397 (13) | 0.0449 (14) | 0.0369 (13) | 0.0021 (11) | 0.0082 (11) | 0.0023 (11) |
C22A | 0.0485 (15) | 0.0479 (15) | 0.0483 (15) | −0.0034 (12) | 0.0069 (13) | −0.0073 (13) |
C23A | 0.0493 (16) | 0.0656 (18) | 0.0462 (16) | 0.0028 (13) | 0.0029 (13) | −0.0111 (14) |
C24A | 0.069 (2) | 0.079 (2) | 0.083 (2) | −0.0044 (17) | 0.0165 (18) | −0.0340 (19) |
C31A | 0.0431 (14) | 0.0350 (12) | 0.0407 (14) | −0.0028 (11) | 0.0059 (11) | −0.0002 (11) |
C32A | 0.0490 (15) | 0.0422 (14) | 0.0531 (16) | 0.0000 (12) | 0.0153 (13) | −0.0013 (12) |
C33A | 0.0730 (19) | 0.0462 (15) | 0.0560 (17) | −0.0051 (14) | 0.0199 (15) | −0.0043 (13) |
C34A | 0.093 (2) | 0.0500 (16) | 0.066 (2) | 0.0072 (16) | 0.0276 (18) | −0.0101 (15) |
C41A | 0.0349 (13) | 0.0385 (13) | 0.0484 (15) | −0.0028 (10) | 0.0051 (11) | 0.0016 (11) |
C42A | 0.0430 (14) | 0.0421 (13) | 0.0452 (14) | −0.0035 (11) | 0.0031 (12) | 0.0019 (12) |
C43A | 0.0399 (14) | 0.0529 (16) | 0.0579 (17) | 0.0005 (12) | 0.0032 (13) | 0.0000 (13) |
C44A | 0.0508 (17) | 0.0596 (17) | 0.0685 (19) | 0.0023 (14) | −0.0082 (15) | 0.0051 (15) |
N2 | 0.0394 (11) | 0.0412 (11) | 0.0523 (13) | −0.0026 (9) | 0.0149 (10) | 0.0011 (10) |
C11B | 0.041 (4) | 0.037 (4) | 0.054 (6) | −0.007 (3) | 0.022 (4) | 0.004 (4) |
C12B | 0.069 (5) | 0.046 (3) | 0.045 (5) | −0.004 (3) | 0.017 (4) | −0.005 (3) |
C13B | 0.106 (5) | 0.058 (4) | 0.063 (5) | −0.011 (3) | 0.029 (5) | −0.011 (4) |
C14B | 0.153 (7) | 0.069 (4) | 0.106 (6) | 0.009 (4) | 0.047 (5) | −0.006 (4) |
C11C | 0.064 (9) | 0.037 (7) | 0.056 (10) | −0.010 (6) | 0.033 (7) | 0.000 (7) |
C12C | 0.059 (7) | 0.052 (6) | 0.038 (8) | −0.008 (5) | 0.005 (7) | 0.005 (5) |
C13C | 0.089 (7) | 0.039 (6) | 0.048 (7) | 0.001 (5) | 0.008 (7) | −0.007 (5) |
C14C | 0.101 (8) | 0.076 (7) | 0.078 (7) | −0.005 (6) | 0.035 (6) | −0.031 (6) |
C21B | 0.0386 (14) | 0.0501 (15) | 0.0592 (17) | 0.0017 (12) | 0.0132 (13) | 0.0060 (13) |
C22B | 0.0532 (18) | 0.0639 (19) | 0.089 (2) | 0.0089 (15) | 0.0155 (17) | 0.0235 (18) |
C23B | 0.0566 (19) | 0.084 (2) | 0.088 (2) | 0.0223 (17) | 0.0136 (18) | 0.022 (2) |
C24D | 0.068 (2) | 0.108 (3) | 0.083 (3) | 0.007 (2) | 0.004 (2) | 0.025 (2) |
C31B | 0.0462 (15) | 0.0426 (14) | 0.0448 (14) | −0.0034 (11) | 0.0144 (12) | 0.0032 (12) |
C32B | 0.0491 (16) | 0.0590 (16) | 0.0508 (16) | −0.0009 (13) | 0.0094 (13) | 0.0038 (14) |
C33B | 0.0589 (18) | 0.0642 (18) | 0.0552 (17) | 0.0073 (15) | 0.0112 (14) | 0.0100 (15) |
C34B | 0.085 (2) | 0.0587 (19) | 0.086 (2) | 0.0119 (17) | 0.015 (2) | 0.0084 (18) |
C41B | 0.0421 (14) | 0.0479 (15) | 0.0461 (15) | 0.0006 (12) | 0.0135 (12) | 0.0061 (12) |
C42B | 0.0518 (16) | 0.0629 (18) | 0.0613 (18) | −0.0039 (14) | 0.0170 (15) | −0.0074 (15) |
C43B | 0.0580 (17) | 0.0592 (17) | 0.0432 (15) | 0.0079 (14) | 0.0093 (14) | 0.0002 (13) |
C44B | 0.082 (2) | 0.084 (2) | 0.073 (2) | 0.0012 (19) | 0.0229 (19) | −0.0195 (19) |
S1A—C1A | 1.674 (3) | C41A—C42A | 1.515 (3) |
O1A—C2A | 1.359 (3) | C41A—H41A | 0.99 |
O1A—C1A | 1.413 (3) | C41A—H41B | 0.99 |
O2A—C4A | 1.351 (3) | C42A—C43A | 1.517 (3) |
O2A—H2A | 0.90 (3) | C42A—H42A | 0.99 |
N1A—C1A | 1.312 (3) | C42A—H42B | 0.99 |
N1A—N2A | 1.408 (3) | C43A—C44A | 1.519 (4) |
N2A—C2A | 1.287 (3) | C43A—H43A | 0.99 |
C2A—C3A | 1.446 (3) | C43A—H43B | 0.99 |
C3A—C8A | 1.394 (3) | C44A—H44A | 0.98 |
C3A—C4A | 1.403 (4) | C44A—H44B | 0.98 |
C4A—C5A | 1.394 (4) | C44A—H44C | 0.98 |
C5A—C6A | 1.382 (4) | N2—C31B | 1.516 (3) |
C5A—H5A | 0.95 | N2—C41B | 1.522 (3) |
C6A—C7A | 1.372 (4) | N2—C21B | 1.522 (3) |
C6A—H6A | 0.95 | N2—C11B | 1.524 (5) |
C7A—C8A | 1.379 (4) | N2—C11C | 1.526 (8) |
C7A—H7A | 0.95 | C11B—C12B | 1.523 (6) |
C8A—H8A | 0.95 | C11B—H11C | 0.99 |
S1B—C1B | 1.684 (2) | C11B—H11D | 0.99 |
O1B—C2B | 1.356 (3) | C12B—C13B | 1.534 (5) |
O1B—C1B | 1.405 (3) | C12B—H12C | 0.99 |
O2B—C4B | 1.360 (3) | C12B—H12D | 0.99 |
O2B—H2B | 0.87 (3) | C13B—C14B | 1.504 (6) |
N1B—C1B | 1.308 (3) | C13B—H13C | 0.99 |
N1B—N2B | 1.410 (3) | C13B—H13D | 0.99 |
N2B—C2B | 1.290 (3) | C14B—H14D | 0.98 |
C2B—C3B | 1.451 (3) | C14B—H14E | 0.98 |
C3B—C8B | 1.393 (3) | C14B—H14F | 0.98 |
C3B—C4B | 1.404 (3) | C11C—C12C | 1.521 (8) |
C4B—C5B | 1.386 (3) | C11C—H11E | 0.99 |
C5B—C6B | 1.375 (4) | C11C—H11F | 0.99 |
C5B—H5B | 0.95 | C12C—C13C | 1.527 (7) |
C6B—C7B | 1.387 (4) | C12C—H12E | 0.99 |
C6B—H6B | 0.95 | C12C—H12F | 0.99 |
C7B—C8B | 1.381 (3) | C13C—C14C | 1.510 (7) |
C7B—H7B | 0.95 | C13C—H13E | 0.99 |
C8B—H8B | 0.95 | C13C—H13F | 0.99 |
N1—C21A | 1.513 (3) | C14C—H14G | 0.98 |
N1—C31A | 1.517 (3) | C14C—H14H | 0.98 |
N1—C41A | 1.521 (3) | C14C—H14I | 0.98 |
N1—C11A | 1.523 (3) | C21B—C22B | 1.518 (4) |
C11A—C12A | 1.516 (3) | C21B—H21C | 0.99 |
C11A—H11A | 0.99 | C21B—H21D | 0.99 |
C11A—H11B | 0.99 | C22B—C23B | 1.528 (4) |
C12A—C13A | 1.511 (4) | C22B—H22C | 0.99 |
C12A—H12A | 0.99 | C22B—H22D | 0.99 |
C12A—H12B | 0.99 | C23B—C24D | 1.508 (5) |
C13A—C14A | 1.518 (4) | C23B—H23C | 0.99 |
C13A—H13A | 0.99 | C23B—H23D | 0.99 |
C13A—H13B | 0.99 | C24D—H24D | 0.98 |
C14A—H14A | 0.98 | C24D—H24E | 0.98 |
C14A—H14B | 0.98 | C24D—H24F | 0.98 |
C14A—H14C | 0.98 | C31B—C32B | 1.520 (3) |
C21A—C22A | 1.516 (3) | C31B—H31C | 0.99 |
C21A—H21A | 0.99 | C31B—H31D | 0.99 |
C21A—H21B | 0.99 | C32B—C33B | 1.530 (4) |
C22A—C23A | 1.521 (4) | C32B—H32C | 0.99 |
C22A—H22A | 0.99 | C32B—H32D | 0.99 |
C22A—H22B | 0.99 | C33B—C34B | 1.515 (4) |
C23A—C24A | 1.524 (4) | C33B—H33C | 0.99 |
C23A—H23A | 0.99 | C33B—H33D | 0.99 |
C23A—H23B | 0.99 | C34B—H34D | 0.98 |
C24A—H24A | 0.98 | C34B—H34E | 0.98 |
C24A—H24B | 0.98 | C34B—H34F | 0.98 |
C24A—H24C | 0.98 | C41B—C42B | 1.516 (3) |
C31A—C32A | 1.517 (3) | C41B—H41C | 0.99 |
C31A—H31A | 0.99 | C41B—H41D | 0.99 |
C31A—H31B | 0.99 | C42B—C43B | 1.513 (4) |
C32A—C33A | 1.513 (3) | C42B—H42C | 0.99 |
C32A—H32A | 0.99 | C42B—H42D | 0.99 |
C32A—H32B | 0.99 | C43B—C44B | 1.508 (4) |
C33A—C34A | 1.523 (4) | C43B—H43C | 0.99 |
C33A—H33A | 0.99 | C43B—H43D | 0.99 |
C33A—H33B | 0.99 | C44B—H44D | 0.98 |
C34A—H34A | 0.98 | C44B—H44E | 0.98 |
C34A—H34B | 0.98 | C44B—H44F | 0.98 |
C34A—H34C | 0.98 | ||
C2A—O1A—C1A | 103.44 (18) | C43A—C42A—H42A | 109.8 |
C4A—O2A—H2A | 108 (2) | C41A—C42A—H42B | 109.8 |
C1A—N1A—N2A | 107.08 (19) | C43A—C42A—H42B | 109.8 |
C2A—N2A—N1A | 107.33 (19) | H42A—C42A—H42B | 108.3 |
N1A—C1A—O1A | 109.6 (2) | C42A—C43A—C44A | 113.0 (2) |
N1A—C1A—S1A | 130.76 (19) | C42A—C43A—H43A | 109.0 |
O1A—C1A—S1A | 119.60 (17) | C44A—C43A—H43A | 109.0 |
N2A—C2A—O1A | 112.5 (2) | C42A—C43A—H43B | 109.0 |
N2A—C2A—C3A | 127.3 (2) | C44A—C43A—H43B | 109.0 |
O1A—C2A—C3A | 120.2 (2) | H43A—C43A—H43B | 107.8 |
C8A—C3A—C4A | 119.2 (2) | C43A—C44A—H44A | 109.5 |
C8A—C3A—C2A | 121.5 (2) | C43A—C44A—H44B | 109.5 |
C4A—C3A—C2A | 119.3 (2) | H44A—C44A—H44B | 109.5 |
O2A—C4A—C5A | 118.3 (3) | C43A—C44A—H44C | 109.5 |
O2A—C4A—C3A | 122.3 (2) | H44A—C44A—H44C | 109.5 |
C5A—C4A—C3A | 119.4 (3) | H44B—C44A—H44C | 109.5 |
C6A—C5A—C4A | 120.0 (3) | C31B—N2—C41B | 110.88 (18) |
C6A—C5A—H5A | 120.0 | C31B—N2—C21B | 106.03 (18) |
C4A—C5A—H5A | 120.0 | C41B—N2—C21B | 110.9 (2) |
C7A—C6A—C5A | 120.9 (3) | C31B—N2—C11B | 108.3 (7) |
C7A—C6A—H6A | 119.6 | C41B—N2—C11B | 109.4 (5) |
C5A—C6A—H6A | 119.6 | C21B—N2—C11B | 111.3 (7) |
C6A—C7A—C8A | 119.8 (3) | C12B—C11B—N2 | 119.6 (6) |
C6A—C7A—H7A | 120.1 | C12B—C11B—H11C | 107.4 |
C8A—C7A—H7A | 120.1 | N2—C11B—H11C | 107.4 |
C7A—C8A—C3A | 120.8 (3) | C12B—C11B—H11D | 107.4 |
C7A—C8A—H8A | 119.6 | N2—C11B—H11D | 107.4 |
C3A—C8A—H8A | 119.6 | H11C—C11B—H11D | 106.9 |
C2B—O1B—C1B | 103.65 (17) | C11B—C12B—C13B | 113.1 (6) |
C4B—O2B—H2B | 113 (2) | C11B—C12B—H12C | 109.0 |
C1B—N1B—N2B | 107.19 (18) | C13B—C12B—H12C | 109.0 |
C2B—N2B—N1B | 106.85 (18) | C11B—C12B—H12D | 109.0 |
N1B—C1B—O1B | 109.81 (19) | C13B—C12B—H12D | 109.0 |
N1B—C1B—S1B | 130.57 (18) | H12C—C12B—H12D | 107.8 |
O1B—C1B—S1B | 119.61 (16) | C14B—C13B—C12B | 112.6 (6) |
N2B—C2B—O1B | 112.5 (2) | C14B—C13B—H13C | 109.1 |
N2B—C2B—C3B | 126.9 (2) | C12B—C13B—H13C | 109.1 |
O1B—C2B—C3B | 120.6 (2) | C14B—C13B—H13D | 109.1 |
C8B—C3B—C4B | 119.0 (2) | C12B—C13B—H13D | 109.1 |
C8B—C3B—C2B | 122.0 (2) | H13C—C13B—H13D | 107.8 |
C4B—C3B—C2B | 119.0 (2) | C13B—C14B—H14D | 109.5 |
O2B—C4B—C5B | 118.0 (2) | C13B—C14B—H14E | 109.5 |
O2B—C4B—C3B | 122.2 (2) | H14D—C14B—H14E | 109.5 |
C5B—C4B—C3B | 119.7 (2) | C13B—C14B—H14F | 109.5 |
C6B—C5B—C4B | 120.3 (2) | H14D—C14B—H14F | 109.5 |
C6B—C5B—H5B | 119.8 | H14E—C14B—H14F | 109.5 |
C4B—C5B—H5B | 119.8 | C12C—C11C—N2 | 107.1 (12) |
C5B—C6B—C7B | 120.6 (3) | C12C—C11C—H11E | 110.3 |
C5B—C6B—H6B | 119.7 | N2—C11C—H11E | 110.3 |
C7B—C6B—H6B | 119.7 | C12C—C11C—H11F | 110.3 |
C8B—C7B—C6B | 119.5 (3) | N2—C11C—H11F | 110.3 |
C8B—C7B—H7B | 120.2 | H11E—C11C—H11F | 108.5 |
C6B—C7B—H7B | 120.2 | C11C—C12C—C13C | 106.3 (10) |
C7B—C8B—C3B | 120.8 (2) | C11C—C12C—H12E | 110.5 |
C7B—C8B—H8B | 119.6 | C13C—C12C—H12E | 110.5 |
C3B—C8B—H8B | 119.6 | C11C—C12C—H12F | 110.5 |
C21A—N1—C31A | 105.77 (17) | C13C—C12C—H12F | 110.5 |
C21A—N1—C41A | 111.64 (18) | H12E—C12C—H12F | 108.7 |
C31A—N1—C41A | 111.14 (17) | C14C—C13C—C12C | 112.6 (11) |
C21A—N1—C11A | 111.74 (18) | C14C—C13C—H13E | 109.1 |
C31A—N1—C11A | 111.30 (17) | C12C—C13C—H13E | 109.1 |
C41A—N1—C11A | 105.37 (17) | C14C—C13C—H13F | 109.1 |
C12A—C11A—N1 | 116.12 (19) | C12C—C13C—H13F | 109.1 |
C12A—C11A—H11A | 108.3 | H13E—C13C—H13F | 107.8 |
N1—C11A—H11A | 108.3 | C13C—C14C—H14G | 109.5 |
C12A—C11A—H11B | 108.3 | C13C—C14C—H14H | 109.5 |
N1—C11A—H11B | 108.3 | H14G—C14C—H14H | 109.5 |
H11A—C11A—H11B | 107.4 | C13C—C14C—H14I | 109.5 |
C13A—C12A—C11A | 110.4 (2) | H14G—C14C—H14I | 109.5 |
C13A—C12A—H12A | 109.6 | H14H—C14C—H14I | 109.5 |
C11A—C12A—H12A | 109.6 | C22B—C21B—N2 | 115.4 (2) |
C13A—C12A—H12B | 109.6 | C22B—C21B—H21C | 108.4 |
C11A—C12A—H12B | 109.6 | N2—C21B—H21C | 108.4 |
H12A—C12A—H12B | 108.1 | C22B—C21B—H21D | 108.4 |
C12A—C13A—C14A | 112.7 (3) | N2—C21B—H21D | 108.4 |
C12A—C13A—H13A | 109.1 | H21C—C21B—H21D | 107.5 |
C14A—C13A—H13A | 109.1 | C21B—C22B—C23B | 110.9 (2) |
C12A—C13A—H13B | 109.1 | C21B—C22B—H22C | 109.5 |
C14A—C13A—H13B | 109.1 | C23B—C22B—H22C | 109.5 |
H13A—C13A—H13B | 107.8 | C21B—C22B—H22D | 109.5 |
C13A—C14A—H14A | 109.5 | C23B—C22B—H22D | 109.5 |
C13A—C14A—H14B | 109.5 | H22C—C22B—H22D | 108.0 |
H14A—C14A—H14B | 109.5 | C24D—C23B—C22B | 112.6 (3) |
C13A—C14A—H14C | 109.5 | C24D—C23B—H23C | 109.1 |
H14A—C14A—H14C | 109.5 | C22B—C23B—H23C | 109.1 |
H14B—C14A—H14C | 109.5 | C24D—C23B—H23D | 109.1 |
N1—C21A—C22A | 116.4 (2) | C22B—C23B—H23D | 109.1 |
N1—C21A—H21A | 108.2 | H23C—C23B—H23D | 107.8 |
C22A—C21A—H21A | 108.2 | C23B—C24D—H24D | 109.5 |
N1—C21A—H21B | 108.2 | C23B—C24D—H24E | 109.5 |
C22A—C21A—H21B | 108.2 | H24D—C24D—H24E | 109.5 |
H21A—C21A—H21B | 107.3 | C23B—C24D—H24F | 109.5 |
C21A—C22A—C23A | 109.4 (2) | H24D—C24D—H24F | 109.5 |
C21A—C22A—H22A | 109.8 | H24E—C24D—H24F | 109.5 |
C23A—C22A—H22A | 109.8 | N2—C31B—C32B | 115.8 (2) |
C21A—C22A—H22B | 109.8 | N2—C31B—H31C | 108.3 |
C23A—C22A—H22B | 109.8 | C32B—C31B—H31C | 108.3 |
H22A—C22A—H22B | 108.2 | N2—C31B—H31D | 108.3 |
C22A—C23A—C24A | 112.1 (2) | C32B—C31B—H31D | 108.3 |
C22A—C23A—H23A | 109.2 | H31C—C31B—H31D | 107.4 |
C24A—C23A—H23A | 109.2 | C31B—C32B—C33B | 110.9 (2) |
C22A—C23A—H23B | 109.2 | C31B—C32B—H32C | 109.5 |
C24A—C23A—H23B | 109.2 | C33B—C32B—H32C | 109.4 |
H23A—C23A—H23B | 107.9 | C31B—C32B—H32D | 109.4 |
C23A—C24A—H24A | 109.5 | C33B—C32B—H32D | 109.4 |
C23A—C24A—H24B | 109.5 | H32C—C32B—H32D | 108.0 |
H24A—C24A—H24B | 109.5 | C34B—C33B—C32B | 114.2 (2) |
C23A—C24A—H24C | 109.5 | C34B—C33B—H33C | 108.7 |
H24A—C24A—H24C | 109.5 | C32B—C33B—H33C | 108.7 |
H24B—C24A—H24C | 109.5 | C34B—C33B—H33D | 108.7 |
N1—C31A—C32A | 115.64 (19) | C32B—C33B—H33D | 108.7 |
N1—C31A—H31A | 108.4 | H33C—C33B—H33D | 107.6 |
C32A—C31A—H31A | 108.4 | C33B—C34B—H34D | 109.5 |
N1—C31A—H31B | 108.4 | C33B—C34B—H34E | 109.5 |
C32A—C31A—H31B | 108.4 | H34D—C34B—H34E | 109.5 |
H31A—C31A—H31B | 107.4 | C33B—C34B—H34F | 109.5 |
C33A—C32A—C31A | 110.0 (2) | H34D—C34B—H34F | 109.5 |
C33A—C32A—H32A | 109.7 | H34E—C34B—H34F | 109.5 |
C31A—C32A—H32A | 109.7 | C42B—C41B—N2 | 115.9 (2) |
C33A—C32A—H32B | 109.7 | C42B—C41B—H41C | 108.3 |
C31A—C32A—H32B | 109.7 | N2—C41B—H41C | 108.3 |
H32A—C32A—H32B | 108.2 | C42B—C41B—H41D | 108.3 |
C32A—C33A—C34A | 112.4 (2) | N2—C41B—H41D | 108.3 |
C32A—C33A—H33A | 109.1 | H41C—C41B—H41D | 107.4 |
C34A—C33A—H33A | 109.1 | C43B—C42B—C41B | 109.8 (2) |
C32A—C33A—H33B | 109.1 | C43B—C42B—H42C | 109.7 |
C34A—C33A—H33B | 109.1 | C41B—C42B—H42C | 109.7 |
H33A—C33A—H33B | 107.9 | C43B—C42B—H42D | 109.7 |
C33A—C34A—H34A | 109.5 | C41B—C42B—H42D | 109.7 |
C33A—C34A—H34B | 109.5 | H42C—C42B—H42D | 108.2 |
H34A—C34A—H34B | 109.5 | C44B—C43B—C42B | 113.6 (2) |
C33A—C34A—H34C | 109.5 | C44B—C43B—H43C | 108.8 |
H34A—C34A—H34C | 109.5 | C42B—C43B—H43C | 108.8 |
H34B—C34A—H34C | 109.5 | C44B—C43B—H43D | 108.8 |
C42A—C41A—N1 | 117.04 (19) | C42B—C43B—H43D | 108.8 |
C42A—C41A—H41A | 108.0 | H43C—C43B—H43D | 107.7 |
N1—C41A—H41A | 108.0 | C43B—C44B—H44D | 109.5 |
C42A—C41A—H41B | 108.0 | C43B—C44B—H44E | 109.5 |
N1—C41A—H41B | 108.0 | H44D—C44B—H44E | 109.5 |
H41A—C41A—H41B | 107.3 | C43B—C44B—H44F | 109.5 |
C41A—C42A—C43A | 109.3 (2) | H44D—C44B—H44F | 109.5 |
C41A—C42A—H42A | 109.8 | H44E—C44B—H44F | 109.5 |
C1A—N1A—N2A—C2A | −0.3 (3) | C6B—C7B—C8B—C3B | −1.2 (5) |
N2A—N1A—C1A—O1A | 0.5 (3) | C4B—C3B—C8B—C7B | 0.7 (4) |
N2A—N1A—C1A—S1A | −178.8 (2) | C2B—C3B—C8B—C7B | −179.3 (3) |
C2A—O1A—C1A—N1A | −0.5 (3) | C21A—N1—C11A—C12A | −65.0 (3) |
C2A—O1A—C1A—S1A | 178.96 (18) | C31A—N1—C11A—C12A | 53.0 (3) |
N1A—N2A—C2A—O1A | 0.0 (3) | C41A—N1—C11A—C12A | 173.5 (2) |
N1A—N2A—C2A—C3A | −178.2 (2) | N1—C11A—C12A—C13A | 176.6 (2) |
C1A—O1A—C2A—N2A | 0.2 (3) | C11A—C12A—C13A—C14A | 166.0 (3) |
C1A—O1A—C2A—C3A | 178.7 (2) | C31A—N1—C21A—C22A | −176.2 (2) |
N2A—C2A—C3A—C8A | −175.8 (3) | C41A—N1—C21A—C22A | 62.8 (2) |
O1A—C2A—C3A—C8A | 6.1 (4) | C11A—N1—C21A—C22A | −54.9 (3) |
N2A—C2A—C3A—C4A | 6.2 (4) | N1—C21A—C22A—C23A | −168.78 (19) |
O1A—C2A—C3A—C4A | −172.0 (2) | C21A—C22A—C23A—C24A | −171.3 (2) |
C8A—C3A—C4A—O2A | −179.8 (2) | C21A—N1—C31A—C32A | −177.51 (19) |
C2A—C3A—C4A—O2A | −1.7 (4) | C41A—N1—C31A—C32A | −56.2 (3) |
C8A—C3A—C4A—C5A | 0.7 (4) | C11A—N1—C31A—C32A | 60.9 (3) |
C2A—C3A—C4A—C5A | 178.8 (3) | N1—C31A—C32A—C33A | −177.0 (2) |
O2A—C4A—C5A—C6A | 179.8 (3) | C31A—C32A—C33A—C34A | −177.7 (2) |
C3A—C4A—C5A—C6A | −0.6 (4) | C21A—N1—C41A—C42A | 58.0 (3) |
C4A—C5A—C6A—C7A | 0.3 (5) | C31A—N1—C41A—C42A | −59.8 (3) |
C5A—C6A—C7A—C8A | 0.1 (5) | C11A—N1—C41A—C42A | 179.5 (2) |
C6A—C7A—C8A—C3A | 0.0 (5) | N1—C41A—C42A—C43A | 170.3 (2) |
C4A—C3A—C8A—C7A | −0.4 (4) | C41A—C42A—C43A—C44A | −179.5 (2) |
C2A—C3A—C8A—C7A | −178.5 (3) | C31B—N2—C11B—C12B | −51.7 (14) |
C1B—N1B—N2B—C2B | −0.2 (3) | C41B—N2—C11B—C12B | −172.7 (10) |
N2B—N1B—C1B—O1B | 0.1 (3) | C21B—N2—C11B—C12B | 64.5 (14) |
N2B—N1B—C1B—S1B | 178.85 (19) | N2—C11B—C12B—C13B | −175.7 (11) |
C2B—O1B—C1B—N1B | 0.0 (2) | C11B—C12B—C13B—C14B | 73.9 (12) |
C2B—O1B—C1B—S1B | −178.86 (17) | N2—C11C—C12C—C13C | −177.2 (18) |
N1B—N2B—C2B—O1B | 0.3 (3) | C11C—C12C—C13C—C14C | −178.2 (18) |
N1B—N2B—C2B—C3B | −178.7 (2) | C31B—N2—C21B—C22B | 173.9 (2) |
C1B—O1B—C2B—N2B | −0.2 (3) | C41B—N2—C21B—C22B | −65.7 (3) |
C1B—O1B—C2B—C3B | 178.8 (2) | C11B—N2—C21B—C22B | 56.3 (6) |
N2B—C2B—C3B—C8B | 178.9 (2) | N2—C21B—C22B—C23B | 161.1 (2) |
O1B—C2B—C3B—C8B | 0.0 (4) | C41B—N2—C31B—C32B | 58.0 (3) |
N2B—C2B—C3B—C4B | −1.1 (4) | C21B—N2—C31B—C32B | 178.4 (2) |
O1B—C2B—C3B—C4B | −180.0 (2) | C11B—N2—C31B—C32B | −62.0 (6) |
C8B—C3B—C4B—O2B | 179.4 (2) | N2—C31B—C32B—C33B | −175.4 (2) |
C2B—C3B—C4B—O2B | −0.7 (4) | C31B—C32B—C33B—C34B | 67.5 (3) |
C8B—C3B—C4B—C5B | 0.2 (4) | C31B—N2—C41B—C42B | 57.2 (3) |
C2B—C3B—C4B—C5B | −179.8 (2) | C21B—N2—C41B—C42B | −60.3 (3) |
O2B—C4B—C5B—C6B | −179.8 (2) | C11B—N2—C41B—C42B | 176.6 (8) |
C3B—C4B—C5B—C6B | −0.7 (4) | N2—C41B—C42B—C43B | −179.5 (2) |
C4B—C5B—C6B—C7B | 0.2 (4) | C41B—C42B—C43B—C44B | −175.9 (2) |
C5B—C6B—C7B—C8B | 0.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2A···N2A | 0.90 (3) | 1.86 (3) | 2.665 (3) | 148 (3) |
O2B—H2B···N2B | 0.87 (3) | 1.90 (3) | 2.645 (3) | 143 (3) |
C11B—H11C···N1Bi | 0.99 | 2.47 | 3.440 (16) | 165 |
C21A—H21A···N1Bi | 0.99 | 2.57 | 3.551 (3) | 172 |
C31B—H31D···O2B | 0.99 | 2.58 | 3.511 (3) | 157 |
C41A—H41B···S1Bii | 0.99 | 2.79 | 3.520 (3) | 131 |
C11C—H11E···N1Bi | 0.99 | 2.42 | 3.38 (3) | 163 |
C41B—H41C···N1A | 0.99 | 2.52 | 3.459 (3) | 157 |
C24B—H24E···Cg1 | 0.99 | 2.92 | 3.863 (3) | 159 |
C42A—H42B···Cg2iii | 0.99 | 2.93 | 3.576 (3) | 125 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H36N+·C8H5N2O2S− |
Mr | 435.66 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 16.600 (6), 13.228 (5), 23.957 (9) |
β (°) | 97.710 (6) |
V (Å3) | 5213 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.51 × 0.43 × 0.23 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.929, 0.967 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 51583, 12911, 5952 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.150, 0.99 |
No. of reflections | 12911 |
No. of parameters | 586 |
No. of restraints | 16 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.31 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2A···N2A | 0.90 (3) | 1.86 (3) | 2.665 (3) | 148 (3) |
O2B—H2B···N2B | 0.87 (3) | 1.90 (3) | 2.645 (3) | 143 (3) |
C11B—H11C···N1Bi | 0.99 | 2.47 | 3.440 (16) | 165 |
C21A—H21A···N1Bi | 0.99 | 2.57 | 3.551 (3) | 172 |
C31B—H31D···O2B | 0.99 | 2.58 | 3.511 (3) | 157 |
C41A—H41B···S1Bii | 0.99 | 2.79 | 3.520 (3) | 131 |
C11C—H11E···N1Bi | 0.99 | 2.42 | 3.38 (3) | 163 |
C41B—H41C···N1A | 0.99 | 2.52 | 3.459 (3) | 157 |
C24B—H24E···Cg1 | 0.99 | 2.92 | 3.863 (3) | 159 |
C42A—H42B···Cg2iii | 0.99 | 2.93 | 3.576 (3) | 125 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z−1/2; (iii) −x+3/2, y+1/2, −z+1/2. |
The title compound was synthesized by the ring closure reaction of the product obtained by the reaction of carbon disulfide with salicylic acid hydrazide in the presence of a base, followed by the addition of tetrabutylammoniumbromide in ethanolic medium.
The compound crystallizes in the monoclinic space group P21/n with two formula units in the asymmetric unit. The contents of the asymmetric unit, together with the atom-labelling scheme, are shown in Fig 1. The bond lengths and angles of the 1,3,4-oxadiazole ring are in good agreement with the values quoted in previous reports (Zhang et al., 2002; Singh et al. 2006, 2007; Stockhouse et al. 2001; Du & Zhao, 2004). The C1A—N1A [1.312 (3) Å] and C1B—N1B [1.308 (3) Å] bond lengths are intermediate between 1.47 Å for a C—N single bond and 1.29 Å for a C═ N double bond, and are significantly longer than the C2A—N2A [1.287 (3) Å] and C2B—N2B [1.290 (3) Å] bond lengths. The C—S bond distances [S1A—C1A = 1.674 (3) Å and S1B—C1B [1.684 (2) Å] are also intermediate between 1.82 Å for a C—S single bond and 1.56 Å for a C═S double bond.
In both molecules, the oxadiazole ring is almost coplanar with the 2-hydroxyphenyl ring. The dihedral angle between the two rings is 6.6 (1)° for molecule A and 1.4 (1)° for molecule B.
The molecular structure of each independent anion is influenced by O2A–H2A···N2A or O2B–H2B···N2B intramolecular hydrogen bonding. In the crystal structure, weak intermolecular C—H···S, C—H···N, and C—H···O interactions are observed (Table 1). In addition, the crystal packing is reinforced by weak intermolecular C—H···π interactions involving the C42A—H42B bond and the O1B/C1B/N1B/N2B/C2B ring [H···ring centroid = 2.92 Å, C21B···ring centroid = 3.578 (3) Å]. Thus the planarity of the two rings, π-electron delocalization, intermolecular and intramolecular interactions all contribute to stabilize the structure of the compound.