organic compounds
5-(Adamantan-1-yl)-3-(benzylsulfanyl)-4-methyl-4H-1,2,4-triazole
aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: hkfun@usm.my
In the 20H25N3S, there are two crystallographic independent molecules with slightly different conformations. In one molecule, the whole benzyl group is disordered over two orientations with the refined site-occupancy ratio of 0.63 (2):0.37 (2). The dihedral angles between the 1,2,4-triazole and phenyl rings are 24.3 (8) (major component) and 25.8 (13)° (minor component) in the disordered molecule, whereas the corresponding angle is 51.53 (16)° in the other molecule. In the crystal, molecules are linked into a chain along the a axis by a weak C—H⋯N interaction. Weak C—H⋯π interactions are also observed.
of the title adamantyl derivative, CRelated literature
For bond-length data, see: Allen et al. (1987). For the synthesis and biological activity of adamantyl-1,2-4-triazole derivatives, see: El-Emam & Ibrahim (1991); El-Emam et al. (2004); Kadi et al. (2007, 2010); Togo et al. (1968). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2012); El-Emam et al. (2012). For a substituted sulfanyl-1,2,4-triazole structure, see: Fun et al. (2011).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812030784/is5162sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030784/is5162Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812030784/is5162Isup3.cml
Sodium methylate (120 mg) was added to a solution of 5-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazole-3-thiol (499 mg, 2 mmol) in absolute ethanol (10 ml) and the mixture was heated under reflux for 10 min. Benzyl bromide (342 mg, 2 mmol) was then added and the mixture was heated under reflux for 3 h. On cooling, the mixture was poured onto water (20 ml) and the precipitated crude product was filtered, washed with water and crystallized from ethanol to yield 475 mg (70%) of the title compound as colorless fine needle crystals. Colorless needle-shaped single crystals of the title compound suitable for X-ray
were recrystalized from chloroform/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days (m.p. 456–458 K).All H atoms were placed in calculated positions with C—H = 0.93 Å for aromatic (phenyl), 0.98 Å for aromatic (adamantyl), 0.97 Å for CH2 and 0.96 Å for CH3 atoms. The Uiso(H) values were constrained to be 1.5Ueq of the
for methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. The whole benzyl group of molecule A is disordered over two sites with refined site occupancies of 0.63 (2) and 0.37 (2). Similarity (SAME) restraint was used for both major and minor components of the disordered group.Derivatives of adamantane have long been known for their diverse biological activities including antiviral activity against the influenza (Togo et al., 1968) and HIV viruses (El-Emam et al., 2004). Moreover, adamantane derivatives were recently reported to exhibit marked antibacterial activity (Kadi et al., 2007, 2010). In an earlier publication, we reported the synthesis and potent anti-inflammatory and analgesic activities of a series of 5-(1-adamantyl)-4-substituted-4H-1,2,4-triazole-3-thiol derivatives including the title compound (I) (El-Emam & Ibrahim, 1991). We, herein reported the
of (I).There are two crystallograpic independent molecules A and B in the
of the title adamantyl derivative, C20H25N3S (Fig. 1). The whole benzyl group of molecule A is disordered over two positions with the refined site-occupancy ratio of 0.63 (2):0.37 (2) for the major and minor components. The 1,2,4-triazole ring is planar with an r.m.s. deviation of 0.001 (2) Å for the disordered molecule A [0.002 (2) Å for molecule B]. The orientation of the benzylsulfanyl moiety with respect to the 1,2,4-triazole ring can be indicated by the dihedral angles between the 1,2,4-triazole and phenyl ring being 24.3 (8) (major component) and 25.8 (13)° (minor component) and the torsion angles C1A–S1A–C13A–C14A = 170.0 (11)° and C1A–S1A–C13X–C14X = -165.8 (13)° for the disordered molecule A [the corresponding dihedral and torsion angles are 51.53 (16) and -163.3 (2)° for molecule B]. The adamantyl group is planarly attached to the 1,2,4-triazole ring at position 5 or atom C2. The bond distances agree with the literature values (Allen et al., 1987) and are comparable with the related structures (Al-Abdullah et al., 2012; El-Emam et al., 2012; Fun et al., 2011).In the crystal packing (Fig. 2), the molecules are linked into chains along the a axis by weak C—H···N interactions (Table 1). The crystal is further stabilized by weak C—H···π interactions (Table 1).
For bond-length data, see: Allen et al. (1987). For the synthesis and biological activity of adamantyl-1,2-4-triazole derivatives, see: El-Emam & Ibrahim (1991); El-Emam et al. (2004); Kadi et al. (2007, 2010); Togo et al. (1968). For related adamantyl-1,2,4-triazole structures, see: Al-Abdullah et al. (2012); El-Emam et al. (2012). For a substituted sulfanyl-1,2,4-triazole structure, see: Fun et al. (2011).
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Open bond show the minor X component. | |
Fig. 2. The crystal packing of the title compound viewed along the b axis. Only the major component and H atoms involved with the hydrogen bond were shown. Weak C—H···N interactions are shown as dashed lines. |
C20H25N3S | Z = 4 |
Mr = 339.49 | F(000) = 728 |
Triclinic, P1 | Dx = 1.256 Mg m−3 |
Hall symbol: -P 1 | Melting point = 456–458 K |
a = 6.4554 (3) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 14.0258 (6) Å | Cell parameters from 6505 reflections |
c = 20.2264 (9) Å | θ = 3.7–69.9° |
α = 94.610 (2)° | µ = 1.63 mm−1 |
β = 95.568 (3)° | T = 296 K |
γ = 98.317 (3)° | Needle, colorless |
V = 1795.23 (14) Å3 | 0.94 × 0.12 × 0.07 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 6505 independent reflections |
Radiation source: fine-focus sealed tube | 4522 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.081 |
φ and ω scans | θmax = 69.9°, θmin = 3.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −6→7 |
Tmin = 0.310, Tmax = 0.900 | k = −17→16 |
22288 measured reflections | l = −24→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.143 | w = 1/[σ2(Fo2) + (0.0644P)2 + 0.2321P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6505 reflections | Δρmax = 0.30 e Å−3 |
500 parameters | Δρmin = −0.26 e Å−3 |
15 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0058 (5) |
C20H25N3S | γ = 98.317 (3)° |
Mr = 339.49 | V = 1795.23 (14) Å3 |
Triclinic, P1 | Z = 4 |
a = 6.4554 (3) Å | Cu Kα radiation |
b = 14.0258 (6) Å | µ = 1.63 mm−1 |
c = 20.2264 (9) Å | T = 296 K |
α = 94.610 (2)° | 0.94 × 0.12 × 0.07 mm |
β = 95.568 (3)° |
Bruker SMART APEXII CCD area-detector diffractometer | 6505 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4522 reflections with I > 2σ(I) |
Tmin = 0.310, Tmax = 0.900 | Rint = 0.081 |
22288 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 15 restraints |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.30 e Å−3 |
6505 reflections | Δρmin = −0.26 e Å−3 |
500 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.13227 (11) | 0.28428 (5) | 0.53379 (3) | 0.0554 (2) | |
N1A | 0.1834 (3) | 0.32730 (13) | 0.67079 (9) | 0.0416 (4) | |
N2A | −0.1139 (3) | 0.35694 (18) | 0.62025 (10) | 0.0612 (6) | |
N3A | −0.1062 (3) | 0.38366 (18) | 0.68787 (10) | 0.0584 (6) | |
C1A | 0.0606 (4) | 0.32387 (17) | 0.61131 (11) | 0.0464 (5) | |
C2A | 0.0710 (3) | 0.36590 (16) | 0.71751 (11) | 0.0416 (5) | |
C3A | 0.1320 (3) | 0.38416 (16) | 0.79177 (11) | 0.0409 (5) | |
C4A | 0.1193 (5) | 0.28829 (18) | 0.82376 (12) | 0.0578 (6) | |
H4AA | 0.2181 | 0.2499 | 0.8058 | 0.069* | |
H4AB | −0.0213 | 0.2519 | 0.8133 | 0.069* | |
C5A | 0.1715 (6) | 0.3083 (2) | 0.89991 (13) | 0.0725 (8) | |
H5AA | 0.1644 | 0.2468 | 0.9201 | 0.087* | |
C6A | 0.0141 (5) | 0.3672 (3) | 0.92805 (14) | 0.0784 (9) | |
H6AA | −0.1273 | 0.3315 | 0.9180 | 0.094* | |
H6AB | 0.0451 | 0.3790 | 0.9762 | 0.094* | |
C7A | 0.0272 (4) | 0.4624 (2) | 0.89753 (13) | 0.0651 (8) | |
H7AA | −0.0744 | 0.5000 | 0.9158 | 0.078* | |
C8A | −0.0260 (4) | 0.4434 (2) | 0.82172 (12) | 0.0585 (7) | |
H8AA | −0.0205 | 0.5045 | 0.8022 | 0.070* | |
H8AB | −0.1677 | 0.4082 | 0.8114 | 0.070* | |
C9A | 0.3527 (4) | 0.4420 (2) | 0.81002 (12) | 0.0556 (6) | |
H9AA | 0.3608 | 0.5034 | 0.7907 | 0.067* | |
H9AB | 0.4557 | 0.4065 | 0.7918 | 0.067* | |
C10A | 0.4030 (4) | 0.4602 (2) | 0.88590 (14) | 0.0639 (7) | |
H10A | 0.5455 | 0.4965 | 0.8966 | 0.077* | |
C11A | 0.2465 (5) | 0.5188 (2) | 0.91453 (14) | 0.0677 (7) | |
H11A | 0.2790 | 0.5309 | 0.9626 | 0.081* | |
H11B | 0.2551 | 0.5806 | 0.8959 | 0.081* | |
C12A | 0.3925 (5) | 0.3650 (2) | 0.91542 (15) | 0.0770 (9) | |
H12A | 0.4289 | 0.3761 | 0.9634 | 0.092* | |
H12B | 0.4930 | 0.3280 | 0.8970 | 0.092* | |
C13A | 0.266 (3) | 0.4010 (6) | 0.5146 (6) | 0.072 (3) | 0.63 (2) |
H13A | 0.1627 | 0.4437 | 0.5064 | 0.087* | 0.63 (2) |
H13B | 0.3635 | 0.4301 | 0.5528 | 0.087* | 0.63 (2) |
C14A | 0.385 (4) | 0.391 (3) | 0.4541 (7) | 0.055 (4) | 0.63 (2) |
C15A | 0.311 (3) | 0.4217 (18) | 0.3953 (9) | 0.053 (2) | 0.63 (2) |
H15A | 0.1837 | 0.4459 | 0.3925 | 0.064* | 0.63 (2) |
C16A | 0.419 (3) | 0.4175 (13) | 0.3401 (5) | 0.057 (3) | 0.63 (2) |
H16A | 0.3656 | 0.4390 | 0.3005 | 0.068* | 0.63 (2) |
C17A | 0.607 (3) | 0.3810 (15) | 0.3441 (7) | 0.068 (4) | 0.63 (2) |
H17A | 0.6836 | 0.3793 | 0.3074 | 0.081* | 0.63 (2) |
C18A | 0.680 (2) | 0.3474 (14) | 0.4020 (10) | 0.067 (3) | 0.63 (2) |
H18A | 0.8012 | 0.3189 | 0.4040 | 0.080* | 0.63 (2) |
C19A | 0.573 (3) | 0.3556 (15) | 0.4580 (7) | 0.063 (4) | 0.63 (2) |
H19A | 0.6289 | 0.3369 | 0.4982 | 0.075* | 0.63 (2) |
C13X | 0.354 (3) | 0.3819 (13) | 0.5293 (7) | 0.058 (3) | 0.37 (2) |
H13E | 0.3137 | 0.4443 | 0.5420 | 0.070* | 0.37 (2) |
H13F | 0.4744 | 0.3732 | 0.5594 | 0.070* | 0.37 (2) |
C14X | 0.407 (7) | 0.377 (4) | 0.4585 (13) | 0.052 (6) | 0.37 (2) |
C15X | 0.293 (5) | 0.417 (3) | 0.4106 (14) | 0.071 (7) | 0.37 (2) |
H15C | 0.1698 | 0.4399 | 0.4202 | 0.086* | 0.37 (2) |
C16X | 0.359 (5) | 0.423 (3) | 0.3479 (13) | 0.073 (7) | 0.37 (2) |
H16C | 0.2839 | 0.4517 | 0.3155 | 0.088* | 0.37 (2) |
C17X | 0.540 (5) | 0.386 (2) | 0.3339 (11) | 0.061 (6) | 0.37 (2) |
H17C | 0.5820 | 0.3874 | 0.2913 | 0.073* | 0.37 (2) |
C18X | 0.657 (4) | 0.348 (3) | 0.3823 (14) | 0.074 (8) | 0.37 (2) |
H18C | 0.7838 | 0.3284 | 0.3738 | 0.088* | 0.37 (2) |
C19X | 0.585 (4) | 0.340 (2) | 0.4441 (11) | 0.053 (5) | 0.37 (2) |
H19C | 0.6560 | 0.3085 | 0.4759 | 0.063* | 0.37 (2) |
C20A | 0.3876 (4) | 0.2937 (2) | 0.67924 (14) | 0.0648 (7) | |
H20A | 0.4063 | 0.2549 | 0.6396 | 0.097* | |
H20B | 0.3928 | 0.2556 | 0.7166 | 0.097* | |
H20C | 0.4978 | 0.3485 | 0.6871 | 0.097* | |
S1B | 0.81154 (13) | 1.08284 (6) | 0.97495 (3) | 0.0710 (2) | |
N1B | 0.8218 (3) | 1.04770 (14) | 0.84119 (9) | 0.0455 (4) | |
N2B | 0.5528 (4) | 1.11795 (19) | 0.86704 (10) | 0.0656 (6) | |
N3B | 0.5424 (3) | 1.10162 (18) | 0.79771 (10) | 0.0613 (6) | |
C1B | 0.7201 (4) | 1.08489 (19) | 0.89102 (12) | 0.0526 (6) | |
C2B | 0.7028 (3) | 1.05931 (17) | 0.78341 (11) | 0.0447 (5) | |
C3B | 0.7402 (3) | 1.02536 (16) | 0.71346 (11) | 0.0410 (5) | |
C4B | 0.7354 (4) | 0.91500 (17) | 0.70604 (13) | 0.0534 (6) | |
H4BA | 0.8480 | 0.8981 | 0.7361 | 0.064* | |
H4BB | 0.6026 | 0.8832 | 0.7181 | 0.064* | |
C5B | 0.7617 (4) | 0.88001 (18) | 0.63401 (12) | 0.0558 (6) | |
H5BA | 0.7602 | 0.8098 | 0.6301 | 0.067* | |
C6B | 0.5816 (4) | 0.90431 (19) | 0.58710 (13) | 0.0568 (6) | |
H6BA | 0.5967 | 0.8816 | 0.5415 | 0.068* | |
H6BB | 0.4483 | 0.8723 | 0.5986 | 0.068* | |
C7B | 0.5847 (4) | 1.01282 (19) | 0.59299 (12) | 0.0526 (6) | |
H7BA | 0.4683 | 1.0284 | 0.5630 | 0.063* | |
C8B | 0.5606 (4) | 1.04849 (19) | 0.66446 (12) | 0.0521 (6) | |
H8BA | 0.4266 | 1.0180 | 0.6765 | 0.063* | |
H8BB | 0.5607 | 1.1179 | 0.6677 | 0.063* | |
C9B | 0.9480 (4) | 1.07541 (19) | 0.69275 (12) | 0.0509 (6) | |
H9BA | 0.9492 | 1.1449 | 0.6959 | 0.061* | |
H9BB | 1.0649 | 1.0623 | 0.7227 | 0.061* | |
C10B | 0.9735 (4) | 1.0386 (2) | 0.62118 (12) | 0.0581 (7) | |
H10B | 1.1079 | 1.0704 | 0.6089 | 0.070* | |
C11B | 0.7932 (5) | 1.0625 (2) | 0.57351 (13) | 0.0609 (7) | |
H11C | 0.7950 | 1.1320 | 0.5761 | 0.073* | |
H11D | 0.8098 | 1.0400 | 0.5280 | 0.073* | |
C12B | 0.9713 (4) | 0.9301 (2) | 0.61595 (13) | 0.0620 (7) | |
H12C | 1.0857 | 0.9147 | 0.6460 | 0.074* | |
H12D | 0.9912 | 0.9072 | 0.5708 | 0.074* | |
C13B | 0.6621 (5) | 1.1680 (2) | 1.01339 (13) | 0.0710 (8) | |
H13C | 0.6613 | 1.2237 | 0.9879 | 0.085* | |
H13D | 0.5176 | 1.1376 | 1.0141 | 0.085* | |
C14B | 0.7628 (5) | 1.1996 (2) | 1.08349 (13) | 0.0596 (7) | |
C15B | 0.6541 (6) | 1.1854 (3) | 1.13763 (16) | 0.0800 (9) | |
H15B | 0.5155 | 1.1540 | 1.1315 | 0.096* | |
C16B | 0.7500 (7) | 1.2179 (3) | 1.20200 (16) | 0.0967 (12) | |
H16B | 0.6737 | 1.2080 | 1.2382 | 0.116* | |
C17B | 0.9476 (7) | 1.2627 (3) | 1.21254 (16) | 0.0865 (10) | |
H17B | 1.0083 | 1.2844 | 1.2557 | 0.104* | |
C18B | 1.0613 (6) | 1.2770 (2) | 1.15988 (17) | 0.0795 (9) | |
H18B | 1.2001 | 1.3080 | 1.1670 | 0.095* | |
C19B | 0.9699 (5) | 1.2450 (2) | 1.09574 (15) | 0.0700 (8) | |
H19B | 1.0491 | 1.2543 | 1.0601 | 0.084* | |
C20B | 1.0230 (4) | 1.0113 (2) | 0.85207 (13) | 0.0618 (7) | |
H20D | 1.1267 | 1.0613 | 0.8761 | 0.093* | |
H20E | 1.0685 | 0.9926 | 0.8098 | 0.093* | |
H20F | 1.0056 | 0.9563 | 0.8775 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0688 (4) | 0.0476 (4) | 0.0462 (3) | −0.0050 (3) | 0.0160 (3) | −0.0043 (2) |
N1A | 0.0366 (10) | 0.0452 (11) | 0.0438 (10) | 0.0068 (7) | 0.0087 (7) | 0.0024 (8) |
N2A | 0.0521 (13) | 0.0891 (17) | 0.0431 (12) | 0.0203 (11) | −0.0010 (9) | −0.0001 (10) |
N3A | 0.0450 (12) | 0.0905 (17) | 0.0419 (11) | 0.0249 (10) | −0.0005 (8) | −0.0002 (10) |
C1A | 0.0489 (14) | 0.0468 (14) | 0.0423 (12) | 0.0023 (10) | 0.0068 (10) | 0.0034 (10) |
C2A | 0.0342 (12) | 0.0474 (13) | 0.0443 (12) | 0.0091 (9) | 0.0078 (9) | 0.0029 (9) |
C3A | 0.0326 (11) | 0.0478 (13) | 0.0428 (12) | 0.0090 (9) | 0.0045 (8) | 0.0011 (9) |
C4A | 0.0772 (18) | 0.0483 (15) | 0.0455 (14) | 0.0044 (12) | 0.0030 (12) | 0.0038 (11) |
C5A | 0.112 (3) | 0.0550 (17) | 0.0461 (15) | 0.0053 (16) | −0.0020 (15) | 0.0065 (12) |
C6A | 0.082 (2) | 0.100 (3) | 0.0439 (15) | −0.0140 (17) | 0.0146 (13) | −0.0037 (15) |
C7A | 0.0567 (16) | 0.089 (2) | 0.0497 (15) | 0.0243 (14) | 0.0064 (11) | −0.0146 (14) |
C8A | 0.0467 (14) | 0.0789 (19) | 0.0519 (14) | 0.0261 (12) | 0.0029 (10) | −0.0086 (12) |
C9A | 0.0371 (13) | 0.0664 (17) | 0.0594 (15) | −0.0004 (11) | 0.0043 (10) | −0.0016 (12) |
C10A | 0.0424 (15) | 0.078 (2) | 0.0634 (16) | −0.0011 (12) | −0.0078 (11) | −0.0091 (14) |
C11A | 0.0755 (19) | 0.0649 (18) | 0.0576 (16) | 0.0122 (14) | −0.0035 (13) | −0.0149 (13) |
C12A | 0.085 (2) | 0.091 (2) | 0.0551 (17) | 0.0361 (17) | −0.0184 (14) | −0.0039 (15) |
C13A | 0.113 (8) | 0.039 (4) | 0.066 (5) | −0.005 (4) | 0.044 (5) | 0.002 (3) |
C14A | 0.072 (7) | 0.041 (11) | 0.049 (8) | −0.003 (4) | 0.019 (6) | −0.006 (5) |
C15A | 0.052 (4) | 0.051 (4) | 0.060 (6) | 0.003 (3) | 0.023 (4) | 0.012 (5) |
C16A | 0.062 (9) | 0.066 (5) | 0.044 (3) | 0.011 (6) | 0.007 (4) | 0.008 (3) |
C17A | 0.069 (8) | 0.079 (6) | 0.060 (8) | 0.017 (5) | 0.024 (6) | 0.007 (5) |
C18A | 0.059 (4) | 0.057 (5) | 0.086 (9) | 0.005 (3) | 0.012 (5) | 0.014 (6) |
C19A | 0.090 (7) | 0.046 (8) | 0.045 (4) | −0.006 (4) | −0.004 (4) | −0.001 (5) |
C13X | 0.073 (8) | 0.039 (7) | 0.058 (6) | −0.005 (4) | 0.018 (5) | −0.007 (4) |
C14X | 0.076 (16) | 0.028 (11) | 0.049 (10) | −0.007 (7) | 0.005 (7) | 0.011 (6) |
C15X | 0.065 (9) | 0.069 (13) | 0.076 (17) | −0.008 (8) | 0.028 (10) | −0.009 (12) |
C16X | 0.066 (14) | 0.069 (8) | 0.090 (14) | 0.021 (9) | 0.012 (9) | 0.017 (9) |
C17X | 0.080 (18) | 0.059 (8) | 0.048 (6) | 0.010 (10) | 0.015 (10) | 0.022 (5) |
C18X | 0.076 (12) | 0.079 (10) | 0.072 (15) | 0.021 (8) | 0.022 (12) | 0.009 (10) |
C19X | 0.069 (9) | 0.030 (8) | 0.052 (11) | −0.004 (4) | 0.000 (8) | −0.005 (8) |
C20A | 0.0534 (16) | 0.085 (2) | 0.0619 (16) | 0.0331 (14) | 0.0120 (12) | −0.0026 (14) |
S1B | 0.0964 (6) | 0.0817 (5) | 0.0435 (4) | 0.0429 (4) | 0.0078 (3) | 0.0052 (3) |
N1B | 0.0460 (11) | 0.0507 (12) | 0.0414 (10) | 0.0135 (8) | 0.0042 (8) | 0.0032 (8) |
N2B | 0.0616 (14) | 0.0924 (18) | 0.0467 (12) | 0.0291 (12) | 0.0085 (10) | −0.0038 (11) |
N3B | 0.0516 (13) | 0.0874 (17) | 0.0479 (12) | 0.0280 (11) | 0.0031 (9) | −0.0050 (11) |
C1B | 0.0553 (15) | 0.0584 (16) | 0.0462 (13) | 0.0163 (11) | 0.0074 (10) | 0.0012 (11) |
C2B | 0.0399 (12) | 0.0504 (14) | 0.0441 (12) | 0.0103 (9) | 0.0024 (9) | 0.0024 (10) |
C3B | 0.0362 (12) | 0.0432 (13) | 0.0428 (12) | 0.0068 (9) | 0.0022 (8) | 0.0003 (9) |
C4B | 0.0592 (15) | 0.0433 (14) | 0.0568 (14) | 0.0067 (11) | 0.0062 (11) | 0.0028 (11) |
C5B | 0.0675 (16) | 0.0426 (14) | 0.0556 (15) | 0.0101 (11) | 0.0053 (12) | −0.0065 (11) |
C6B | 0.0486 (15) | 0.0590 (16) | 0.0555 (15) | −0.0034 (11) | −0.0008 (11) | −0.0094 (12) |
C7B | 0.0501 (14) | 0.0594 (16) | 0.0458 (13) | 0.0122 (11) | −0.0066 (10) | −0.0027 (11) |
C8B | 0.0475 (14) | 0.0574 (15) | 0.0506 (14) | 0.0158 (11) | −0.0035 (10) | −0.0039 (11) |
C9B | 0.0431 (13) | 0.0530 (15) | 0.0509 (14) | −0.0035 (10) | 0.0006 (10) | −0.0043 (11) |
C10B | 0.0463 (14) | 0.0742 (19) | 0.0476 (14) | −0.0099 (11) | 0.0088 (10) | −0.0023 (12) |
C11B | 0.0711 (18) | 0.0626 (17) | 0.0440 (14) | −0.0038 (13) | 0.0035 (12) | 0.0037 (11) |
C12B | 0.0495 (15) | 0.080 (2) | 0.0560 (15) | 0.0184 (13) | 0.0066 (11) | −0.0137 (13) |
C13B | 0.079 (2) | 0.086 (2) | 0.0532 (16) | 0.0326 (16) | 0.0101 (13) | 0.0007 (14) |
C14B | 0.080 (2) | 0.0537 (16) | 0.0516 (15) | 0.0260 (13) | 0.0173 (13) | 0.0057 (11) |
C15B | 0.089 (2) | 0.084 (2) | 0.0680 (19) | 0.0085 (17) | 0.0321 (17) | −0.0047 (16) |
C16B | 0.130 (3) | 0.105 (3) | 0.0550 (19) | 0.006 (2) | 0.038 (2) | −0.0045 (18) |
C17B | 0.129 (3) | 0.073 (2) | 0.0564 (19) | 0.021 (2) | 0.0066 (19) | −0.0063 (15) |
C18B | 0.088 (2) | 0.064 (2) | 0.083 (2) | 0.0131 (16) | −0.0019 (17) | 0.0020 (16) |
C19B | 0.085 (2) | 0.073 (2) | 0.0595 (17) | 0.0221 (16) | 0.0185 (15) | 0.0159 (14) |
C20B | 0.0616 (17) | 0.0743 (19) | 0.0538 (15) | 0.0314 (13) | −0.0012 (11) | 0.0030 (13) |
S1A—C1A | 1.748 (2) | C17X—H17C | 0.9300 |
S1A—C13A | 1.826 (8) | C18X—C19X | 1.384 (14) |
S1A—C13X | 1.845 (15) | C18X—H18C | 0.9300 |
N1A—C1A | 1.368 (3) | C19X—H19C | 0.9300 |
N1A—C2A | 1.370 (3) | C20A—H20A | 0.9600 |
N1A—C20A | 1.462 (3) | C20A—H20B | 0.9600 |
N2A—C1A | 1.301 (3) | C20A—H20C | 0.9600 |
N2A—N3A | 1.383 (3) | S1B—C1B | 1.746 (2) |
N3A—C2A | 1.305 (3) | S1B—C13B | 1.814 (3) |
C2A—C3A | 1.507 (3) | N1B—C1B | 1.364 (3) |
C3A—C9A | 1.530 (3) | N1B—C2B | 1.369 (3) |
C3A—C4A | 1.534 (3) | N1B—C20B | 1.466 (3) |
C3A—C8A | 1.543 (3) | N2B—C1B | 1.303 (3) |
C4A—C5A | 1.539 (3) | N2B—N3B | 1.396 (3) |
C4A—H4AA | 0.9700 | N3B—C2B | 1.310 (3) |
C4A—H4AB | 0.9700 | C2B—C3B | 1.509 (3) |
C5A—C12A | 1.520 (5) | C3B—C9B | 1.534 (3) |
C5A—C6A | 1.523 (5) | C3B—C4B | 1.539 (3) |
C5A—H5AA | 0.9800 | C3B—C8B | 1.539 (3) |
C6A—C7A | 1.511 (5) | C4B—C5B | 1.533 (3) |
C6A—H6AA | 0.9700 | C4B—H4BA | 0.9700 |
C6A—H6AB | 0.9700 | C4B—H4BB | 0.9700 |
C7A—C11A | 1.512 (4) | C5B—C12B | 1.523 (4) |
C7A—C8A | 1.531 (3) | C5B—C6B | 1.523 (4) |
C7A—H7AA | 0.9800 | C5B—H5BA | 0.9800 |
C8A—H8AA | 0.9700 | C6B—C7B | 1.514 (4) |
C8A—H8AB | 0.9700 | C6B—H6BA | 0.9700 |
C9A—C10A | 1.531 (4) | C6B—H6BB | 0.9700 |
C9A—H9AA | 0.9700 | C7B—C8B | 1.521 (3) |
C9A—H9AB | 0.9700 | C7B—C11B | 1.526 (4) |
C10A—C12A | 1.502 (5) | C7B—H7BA | 0.9800 |
C10A—C11A | 1.519 (4) | C8B—H8BA | 0.9700 |
C10A—H10A | 0.9800 | C8B—H8BB | 0.9700 |
C11A—H11A | 0.9700 | C9B—C10B | 1.529 (3) |
C11A—H11B | 0.9700 | C9B—H9BA | 0.9700 |
C12A—H12A | 0.9700 | C9B—H9BB | 0.9700 |
C12A—H12B | 0.9700 | C10B—C12B | 1.516 (4) |
C13A—C14A | 1.516 (8) | C10B—C11B | 1.531 (4) |
C13A—H13A | 0.9700 | C10B—H10B | 0.9800 |
C13A—H13B | 0.9700 | C11B—H11C | 0.9700 |
C14A—C15A | 1.362 (10) | C11B—H11D | 0.9700 |
C14A—C19A | 1.376 (11) | C12B—H12C | 0.9700 |
C15A—C16A | 1.373 (10) | C12B—H12D | 0.9700 |
C15A—H15A | 0.9300 | C13B—C14B | 1.505 (4) |
C16A—C17A | 1.384 (10) | C13B—H13C | 0.9700 |
C16A—H16A | 0.9300 | C13B—H13D | 0.9700 |
C17A—C18A | 1.365 (11) | C14B—C15B | 1.369 (4) |
C17A—H17A | 0.9300 | C14B—C19B | 1.385 (4) |
C18A—C19A | 1.385 (10) | C15B—C16B | 1.397 (5) |
C18A—H18A | 0.9300 | C15B—H15B | 0.9300 |
C19A—H19A | 0.9300 | C16B—C17B | 1.327 (5) |
C13X—C14X | 1.504 (14) | C16B—H16B | 0.9300 |
C13X—H13E | 0.9700 | C17B—C18B | 1.363 (5) |
C13X—H13F | 0.9700 | C17B—H17B | 0.9300 |
C14X—C15X | 1.362 (15) | C18B—C19B | 1.383 (4) |
C14X—C19X | 1.374 (14) | C18B—H18B | 0.9300 |
C15X—C16X | 1.384 (14) | C19B—H19B | 0.9300 |
C15X—H15C | 0.9300 | C20B—H20D | 0.9600 |
C16X—C17X | 1.385 (14) | C20B—H20E | 0.9600 |
C16X—H16C | 0.9300 | C20B—H20F | 0.9600 |
C17X—C18X | 1.367 (15) | ||
C1A—S1A—C13A | 97.2 (2) | C17X—C18X—C19X | 119.4 (15) |
C1A—S1A—C13X | 98.2 (4) | C17X—C18X—H18C | 120.3 |
C1A—N1A—C2A | 105.04 (18) | C19X—C18X—H18C | 120.3 |
C1A—N1A—C20A | 125.09 (19) | C14X—C19X—C18X | 120.1 (15) |
C2A—N1A—C20A | 129.9 (2) | C14X—C19X—H19C | 120.0 |
C1A—N2A—N3A | 106.63 (19) | C18X—C19X—H19C | 120.0 |
C2A—N3A—N2A | 108.67 (18) | N1A—C20A—H20A | 109.5 |
N2A—C1A—N1A | 110.59 (19) | N1A—C20A—H20B | 109.5 |
N2A—C1A—S1A | 124.74 (19) | H20A—C20A—H20B | 109.5 |
N1A—C1A—S1A | 124.64 (17) | N1A—C20A—H20C | 109.5 |
N3A—C2A—N1A | 109.07 (19) | H20A—C20A—H20C | 109.5 |
N3A—C2A—C3A | 123.56 (18) | H20B—C20A—H20C | 109.5 |
N1A—C2A—C3A | 127.36 (19) | C1B—S1B—C13B | 100.25 (12) |
C2A—C3A—C9A | 112.91 (18) | C1B—N1B—C2B | 104.86 (18) |
C2A—C3A—C4A | 110.55 (19) | C1B—N1B—C20B | 124.2 (2) |
C9A—C3A—C4A | 109.2 (2) | C2B—N1B—C20B | 130.82 (19) |
C2A—C3A—C8A | 108.14 (18) | C1B—N2B—N3B | 106.24 (19) |
C9A—C3A—C8A | 107.7 (2) | C2B—N3B—N2B | 108.07 (19) |
C4A—C3A—C8A | 108.2 (2) | N2B—C1B—N1B | 111.3 (2) |
C3A—C4A—C5A | 109.9 (2) | N2B—C1B—S1B | 127.25 (18) |
C3A—C4A—H4AA | 109.7 | N1B—C1B—S1B | 121.46 (18) |
C5A—C4A—H4AA | 109.7 | N3B—C2B—N1B | 109.56 (19) |
C3A—C4A—H4AB | 109.7 | N3B—C2B—C3B | 124.0 (2) |
C5A—C4A—H4AB | 109.7 | N1B—C2B—C3B | 126.43 (19) |
H4AA—C4A—H4AB | 108.2 | C2B—C3B—C9B | 113.09 (18) |
C12A—C5A—C6A | 109.5 (2) | C2B—C3B—C4B | 110.45 (19) |
C12A—C5A—C4A | 109.0 (3) | C9B—C3B—C4B | 109.48 (19) |
C6A—C5A—C4A | 109.6 (3) | C2B—C3B—C8B | 108.56 (17) |
C12A—C5A—H5AA | 109.6 | C9B—C3B—C8B | 107.48 (19) |
C6A—C5A—H5AA | 109.6 | C4B—C3B—C8B | 107.58 (19) |
C4A—C5A—H5AA | 109.6 | C5B—C4B—C3B | 110.3 (2) |
C7A—C6A—C5A | 109.5 (2) | C5B—C4B—H4BA | 109.6 |
C7A—C6A—H6AA | 109.8 | C3B—C4B—H4BA | 109.6 |
C5A—C6A—H6AA | 109.8 | C5B—C4B—H4BB | 109.6 |
C7A—C6A—H6AB | 109.8 | C3B—C4B—H4BB | 109.6 |
C5A—C6A—H6AB | 109.8 | H4BA—C4B—H4BB | 108.1 |
H6AA—C6A—H6AB | 108.2 | C12B—C5B—C6B | 109.9 (2) |
C6A—C7A—C11A | 109.5 (3) | C12B—C5B—C4B | 109.0 (2) |
C6A—C7A—C8A | 109.6 (2) | C6B—C5B—C4B | 109.5 (2) |
C11A—C7A—C8A | 110.3 (2) | C12B—C5B—H5BA | 109.5 |
C6A—C7A—H7AA | 109.1 | C6B—C5B—H5BA | 109.5 |
C11A—C7A—H7AA | 109.1 | C4B—C5B—H5BA | 109.5 |
C8A—C7A—H7AA | 109.1 | C7B—C6B—C5B | 109.38 (19) |
C7A—C8A—C3A | 110.15 (19) | C7B—C6B—H6BA | 109.8 |
C7A—C8A—H8AA | 109.6 | C5B—C6B—H6BA | 109.8 |
C3A—C8A—H8AA | 109.6 | C7B—C6B—H6BB | 109.8 |
C7A—C8A—H8AB | 109.6 | C5B—C6B—H6BB | 109.8 |
C3A—C8A—H8AB | 109.6 | H6BA—C6B—H6BB | 108.2 |
H8AA—C8A—H8AB | 108.1 | C6B—C7B—C8B | 109.8 (2) |
C3A—C9A—C10A | 110.3 (2) | C6B—C7B—C11B | 109.4 (2) |
C3A—C9A—H9AA | 109.6 | C8B—C7B—C11B | 109.4 (2) |
C10A—C9A—H9AA | 109.6 | C6B—C7B—H7BA | 109.4 |
C3A—C9A—H9AB | 109.6 | C8B—C7B—H7BA | 109.4 |
C10A—C9A—H9AB | 109.6 | C11B—C7B—H7BA | 109.4 |
H9AA—C9A—H9AB | 108.1 | C7B—C8B—C3B | 111.25 (19) |
C12A—C10A—C11A | 110.1 (3) | C7B—C8B—H8BA | 109.4 |
C12A—C10A—C9A | 109.4 (2) | C3B—C8B—H8BA | 109.4 |
C11A—C10A—C9A | 109.8 (2) | C7B—C8B—H8BB | 109.4 |
C12A—C10A—H10A | 109.2 | C3B—C8B—H8BB | 109.4 |
C11A—C10A—H10A | 109.2 | H8BA—C8B—H8BB | 108.0 |
C9A—C10A—H10A | 109.2 | C10B—C9B—C3B | 110.14 (19) |
C7A—C11A—C10A | 108.8 (2) | C10B—C9B—H9BA | 109.6 |
C7A—C11A—H11A | 109.9 | C3B—C9B—H9BA | 109.6 |
C10A—C11A—H11A | 109.9 | C10B—C9B—H9BB | 109.6 |
C7A—C11A—H11B | 109.9 | C3B—C9B—H9BB | 109.6 |
C10A—C11A—H11B | 109.9 | H9BA—C9B—H9BB | 108.1 |
H11A—C11A—H11B | 108.3 | C12B—C10B—C9B | 109.9 (2) |
C10A—C12A—C5A | 109.8 (2) | C12B—C10B—C11B | 109.5 (2) |
C10A—C12A—H12A | 109.7 | C9B—C10B—C11B | 109.7 (2) |
C5A—C12A—H12A | 109.7 | C12B—C10B—H10B | 109.2 |
C10A—C12A—H12B | 109.7 | C9B—C10B—H10B | 109.2 |
C5A—C12A—H12B | 109.7 | C11B—C10B—H10B | 109.2 |
H12A—C12A—H12B | 108.2 | C7B—C11B—C10B | 108.9 (2) |
C14A—C13A—S1A | 112.2 (15) | C7B—C11B—H11C | 109.9 |
C14A—C13A—H13A | 109.2 | C10B—C11B—H11C | 109.9 |
S1A—C13A—H13A | 109.2 | C7B—C11B—H11D | 109.9 |
C14A—C13A—H13B | 109.2 | C10B—C11B—H11D | 109.9 |
S1A—C13A—H13B | 109.2 | H11C—C11B—H11D | 108.3 |
H13A—C13A—H13B | 107.9 | C10B—C12B—C5B | 109.7 (2) |
C15A—C14A—C19A | 119.0 (8) | C10B—C12B—H12C | 109.7 |
C15A—C14A—C13A | 119.9 (11) | C5B—C12B—H12C | 109.7 |
C19A—C14A—C13A | 121.0 (11) | C10B—C12B—H12D | 109.7 |
C14A—C15A—C16A | 121.5 (8) | C5B—C12B—H12D | 109.7 |
C14A—C15A—H15A | 119.2 | H12C—C12B—H12D | 108.2 |
C16A—C15A—H15A | 119.2 | C14B—C13B—S1B | 108.66 (19) |
C15A—C16A—C17A | 119.4 (9) | C14B—C13B—H13C | 110.0 |
C15A—C16A—H16A | 120.3 | S1B—C13B—H13C | 110.0 |
C17A—C16A—H16A | 120.3 | C14B—C13B—H13D | 110.0 |
C18A—C17A—C16A | 119.5 (10) | S1B—C13B—H13D | 110.0 |
C18A—C17A—H17A | 120.2 | H13C—C13B—H13D | 108.3 |
C16A—C17A—H17A | 120.2 | C15B—C14B—C19B | 117.2 (3) |
C17A—C18A—C19A | 120.4 (11) | C15B—C14B—C13B | 121.7 (3) |
C17A—C18A—H18A | 119.8 | C19B—C14B—C13B | 121.1 (3) |
C19A—C18A—H18A | 119.8 | C14B—C15B—C16B | 120.4 (3) |
C14A—C19A—C18A | 120.0 (10) | C14B—C15B—H15B | 119.8 |
C14A—C19A—H19A | 120.0 | C16B—C15B—H15B | 119.8 |
C18A—C19A—H19A | 120.0 | C17B—C16B—C15B | 121.4 (3) |
C14X—C13X—S1A | 108 (3) | C17B—C16B—H16B | 119.3 |
C14X—C13X—H13E | 110.2 | C15B—C16B—H16B | 119.3 |
S1A—C13X—H13E | 110.2 | C16B—C17B—C18B | 119.8 (3) |
C14X—C13X—H13F | 110.2 | C16B—C17B—H17B | 120.1 |
S1A—C13X—H13F | 110.2 | C18B—C17B—H17B | 120.1 |
H13E—C13X—H13F | 108.5 | C17B—C18B—C19B | 119.8 (4) |
C15X—C14X—C19X | 120.4 (14) | C17B—C18B—H18B | 120.1 |
C15X—C14X—C13X | 120.8 (18) | C19B—C18B—H18B | 120.1 |
C19X—C14X—C13X | 118.6 (17) | C18B—C19B—C14B | 121.4 (3) |
C14X—C15X—C16X | 120.1 (17) | C18B—C19B—H19B | 119.3 |
C14X—C15X—H15C | 119.9 | C14B—C19B—H19B | 119.3 |
C16X—C15X—H15C | 119.9 | N1B—C20B—H20D | 109.5 |
C15X—C16X—C17X | 119.2 (17) | N1B—C20B—H20E | 109.5 |
C15X—C16X—H16C | 120.4 | H20D—C20B—H20E | 109.5 |
C17X—C16X—H16C | 120.4 | N1B—C20B—H20F | 109.5 |
C18X—C17X—C16X | 120.6 (15) | H20D—C20B—H20F | 109.5 |
C18X—C17X—H17C | 119.7 | H20E—C20B—H20F | 109.5 |
C16X—C17X—H17C | 119.7 | ||
C1A—N2A—N3A—C2A | −0.1 (3) | C13X—C14X—C15X—C16X | 172 (4) |
N3A—N2A—C1A—N1A | 0.3 (3) | C14X—C15X—C16X—C17X | 2 (7) |
N3A—N2A—C1A—S1A | −177.74 (18) | C15X—C16X—C17X—C18X | −3 (6) |
C2A—N1A—C1A—N2A | −0.4 (3) | C16X—C17X—C18X—C19X | 5 (6) |
C20A—N1A—C1A—N2A | 178.5 (2) | C15X—C14X—C19X—C18X | 5 (8) |
C2A—N1A—C1A—S1A | 177.69 (17) | C13X—C14X—C19X—C18X | −170 (4) |
C20A—N1A—C1A—S1A | −3.5 (3) | C17X—C18X—C19X—C14X | −6 (6) |
C13A—S1A—C1A—N2A | 89.2 (6) | C1B—N2B—N3B—C2B | 0.3 (3) |
C13X—S1A—C1A—N2A | 111.7 (7) | N3B—N2B—C1B—N1B | 0.2 (3) |
C13A—S1A—C1A—N1A | −88.6 (6) | N3B—N2B—C1B—S1B | −178.5 (2) |
C13X—S1A—C1A—N1A | −66.1 (7) | C2B—N1B—C1B—N2B | −0.5 (3) |
N2A—N3A—C2A—N1A | −0.1 (3) | C20B—N1B—C1B—N2B | 175.5 (3) |
N2A—N3A—C2A—C3A | −178.8 (2) | C2B—N1B—C1B—S1B | 178.19 (18) |
C1A—N1A—C2A—N3A | 0.3 (3) | C20B—N1B—C1B—S1B | −5.8 (4) |
C20A—N1A—C2A—N3A | −178.5 (3) | C13B—S1B—C1B—N2B | −16.1 (3) |
C1A—N1A—C2A—C3A | 178.9 (2) | C13B—S1B—C1B—N1B | 165.4 (2) |
C20A—N1A—C2A—C3A | 0.1 (4) | N2B—N3B—C2B—N1B | −0.6 (3) |
N3A—C2A—C3A—C9A | −129.8 (2) | N2B—N3B—C2B—C3B | 176.8 (2) |
N1A—C2A—C3A—C9A | 51.8 (3) | C1B—N1B—C2B—N3B | 0.7 (3) |
N3A—C2A—C3A—C4A | 107.6 (3) | C20B—N1B—C2B—N3B | −174.9 (3) |
N1A—C2A—C3A—C4A | −70.9 (3) | C1B—N1B—C2B—C3B | −176.6 (2) |
N3A—C2A—C3A—C8A | −10.7 (3) | C20B—N1B—C2B—C3B | 7.7 (4) |
N1A—C2A—C3A—C8A | 170.8 (2) | N3B—C2B—C3B—C9B | 118.8 (3) |
C2A—C3A—C4A—C5A | −177.3 (2) | N1B—C2B—C3B—C9B | −64.2 (3) |
C9A—C3A—C4A—C5A | 58.0 (3) | N3B—C2B—C3B—C4B | −118.1 (3) |
C8A—C3A—C4A—C5A | −59.0 (3) | N1B—C2B—C3B—C4B | 58.9 (3) |
C3A—C4A—C5A—C12A | −59.6 (3) | N3B—C2B—C3B—C8B | −0.3 (3) |
C3A—C4A—C5A—C6A | 60.2 (3) | N1B—C2B—C3B—C8B | 176.7 (2) |
C12A—C5A—C6A—C7A | 59.1 (3) | C2B—C3B—C4B—C5B | 177.00 (19) |
C4A—C5A—C6A—C7A | −60.4 (3) | C9B—C3B—C4B—C5B | −57.8 (3) |
C5A—C6A—C7A—C11A | −60.6 (3) | C8B—C3B—C4B—C5B | 58.7 (3) |
C5A—C6A—C7A—C8A | 60.5 (3) | C3B—C4B—C5B—C12B | 59.6 (3) |
C6A—C7A—C8A—C3A | −60.5 (3) | C3B—C4B—C5B—C6B | −60.7 (3) |
C11A—C7A—C8A—C3A | 60.2 (3) | C12B—C5B—C6B—C7B | −59.6 (3) |
C2A—C3A—C8A—C7A | 179.0 (2) | C4B—C5B—C6B—C7B | 60.2 (3) |
C9A—C3A—C8A—C7A | −58.7 (3) | C5B—C6B—C7B—C8B | −59.6 (3) |
C4A—C3A—C8A—C7A | 59.2 (3) | C5B—C6B—C7B—C11B | 60.6 (3) |
C2A—C3A—C9A—C10A | 178.6 (2) | C6B—C7B—C8B—C3B | 59.8 (3) |
C4A—C3A—C9A—C10A | −58.0 (3) | C11B—C7B—C8B—C3B | −60.3 (3) |
C8A—C3A—C9A—C10A | 59.3 (3) | C2B—C3B—C8B—C7B | −178.0 (2) |
C3A—C9A—C10A—C12A | 59.8 (3) | C9B—C3B—C8B—C7B | 59.3 (3) |
C3A—C9A—C10A—C11A | −61.1 (3) | C4B—C3B—C8B—C7B | −58.5 (3) |
C6A—C7A—C11A—C10A | 60.8 (3) | C2B—C3B—C9B—C10B | −179.1 (2) |
C8A—C7A—C11A—C10A | −59.9 (3) | C4B—C3B—C9B—C10B | 57.3 (3) |
C12A—C10A—C11A—C7A | −60.4 (3) | C8B—C3B—C9B—C10B | −59.3 (3) |
C9A—C10A—C11A—C7A | 60.1 (3) | C3B—C9B—C10B—C12B | −59.2 (3) |
C11A—C10A—C12A—C5A | 59.5 (3) | C3B—C9B—C10B—C11B | 61.3 (3) |
C9A—C10A—C12A—C5A | −61.3 (3) | C6B—C7B—C11B—C10B | −60.9 (3) |
C6A—C5A—C12A—C10A | −58.6 (3) | C8B—C7B—C11B—C10B | 59.5 (3) |
C4A—C5A—C12A—C10A | 61.3 (3) | C12B—C10B—C11B—C7B | 60.4 (3) |
C1A—S1A—C13A—C14A | 170.0 (11) | C9B—C10B—C11B—C7B | −60.3 (3) |
C13X—S1A—C13A—C14A | 75.9 (17) | C9B—C10B—C12B—C5B | 60.9 (3) |
S1A—C13A—C14A—C15A | 107 (3) | C11B—C10B—C12B—C5B | −59.6 (3) |
S1A—C13A—C14A—C19A | −75 (3) | C6B—C5B—C12B—C10B | 59.2 (3) |
C19A—C14A—C15A—C16A | 0 (5) | C4B—C5B—C12B—C10B | −60.9 (3) |
C13A—C14A—C15A—C16A | 178 (2) | C1B—S1B—C13B—C14B | −163.3 (2) |
C14A—C15A—C16A—C17A | 0 (4) | S1B—C13B—C14B—C15B | −121.0 (3) |
C15A—C16A—C17A—C18A | 2 (3) | S1B—C13B—C14B—C19B | 59.6 (3) |
C16A—C17A—C18A—C19A | −4 (3) | C19B—C14B—C15B—C16B | 1.3 (5) |
C15A—C14A—C19A—C18A | −2 (5) | C13B—C14B—C15B—C16B | −178.2 (3) |
C13A—C14A—C19A—C18A | 180 (2) | C14B—C15B—C16B—C17B | −0.2 (6) |
C17A—C18A—C19A—C14A | 5 (4) | C15B—C16B—C17B—C18B | −0.6 (6) |
C1A—S1A—C13X—C14X | −165.8 (13) | C16B—C17B—C18B—C19B | 0.3 (5) |
C13A—S1A—C13X—C14X | −76.9 (18) | C17B—C18B—C19B—C14B | 0.8 (5) |
S1A—C13X—C14X—C15X | 81 (6) | C15B—C14B—C19B—C18B | −1.5 (4) |
S1A—C13X—C14X—C19X | −104 (5) | C13B—C14B—C19B—C18B | 177.9 (3) |
C19X—C14X—C15X—C16X | −3 (9) |
Cg1, Cg2 and Cg3 are the centroids of the C14A–C19A, N1B–N3B/C1B–C2B and C14B–C19B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C20A—H20C···N3Ai | 0.96 | 2.53 | 3.311 (3) | 138 |
C4A—H4AB···Cg2ii | 0.97 | 2.98 | 3.837 (3) | 148 |
C5B—H5BA···Cg1iii | 0.98 | 2.97 | 3.833 (11) | 147 |
C13A—H13B···Cg1iii | 0.97 | 2.68 | 3.418 (14) | 133 |
C20B—H20F···Cg3iv | 0.96 | 2.92 | 3.595 (3) | 128 |
C13X—H13E···Cg1iii | 0.97 | 2.65 | 3.42 (2) | 137 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+2, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C20H25N3S |
Mr | 339.49 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 6.4554 (3), 14.0258 (6), 20.2264 (9) |
α, β, γ (°) | 94.610 (2), 95.568 (3), 98.317 (3) |
V (Å3) | 1795.23 (14) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.63 |
Crystal size (mm) | 0.94 × 0.12 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.310, 0.900 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 22288, 6505, 4522 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.143, 1.03 |
No. of reflections | 6505 |
No. of parameters | 500 |
No. of restraints | 15 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.26 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1, Cg2 and Cg3 are the centroids of the C14A–C19A, N1B–N3B/C1B–C2B and C14B–C19B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C20A—H20C···N3Ai | 0.96 | 2.53 | 3.311 (3) | 138 |
C4A—H4AB···Cg2ii | 0.97 | 2.98 | 3.837 (3) | 148 |
C5B—H5BA···Cg1iii | 0.98 | 2.97 | 3.833 (11) | 147 |
C13A—H13B···Cg1iii | 0.97 | 2.68 | 3.418 (14) | 133 |
C20B—H20F···Cg3iv | 0.96 | 2.92 | 3.595 (3) | 128 |
C13X—H13E···Cg1iii | 0.97 | 2.65 | 3.42 (2) | 137 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) −x+2, −y+2, −z+2. |
Acknowledgements
The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. HKF and SC thank the Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Derivatives of adamantane have long been known for their diverse biological activities including antiviral activity against the influenza (Togo et al., 1968) and HIV viruses (El-Emam et al., 2004). Moreover, adamantane derivatives were recently reported to exhibit marked antibacterial activity (Kadi et al., 2007, 2010). In an earlier publication, we reported the synthesis and potent anti-inflammatory and analgesic activities of a series of 5-(1-adamantyl)-4-substituted-4H-1,2,4-triazole-3-thiol derivatives including the title compound (I) (El-Emam & Ibrahim, 1991). We, herein reported the crystal structure of (I).
There are two crystallograpic independent molecules A and B in the asymmetric unit of the title adamantyl derivative, C20H25N3S (Fig. 1). The whole benzyl group of molecule A is disordered over two positions with the refined site-occupancy ratio of 0.63 (2):0.37 (2) for the major and minor components. The 1,2,4-triazole ring is planar with an r.m.s. deviation of 0.001 (2) Å for the disordered molecule A [0.002 (2) Å for molecule B]. The orientation of the benzylsulfanyl moiety with respect to the 1,2,4-triazole ring can be indicated by the dihedral angles between the 1,2,4-triazole and phenyl ring being 24.3 (8) (major component) and 25.8 (13)° (minor component) and the torsion angles C1A–S1A–C13A–C14A = 170.0 (11)° and C1A–S1A–C13X–C14X = -165.8 (13)° for the disordered molecule A [the corresponding dihedral and torsion angles are 51.53 (16) and -163.3 (2)° for molecule B]. The adamantyl group is planarly attached to the 1,2,4-triazole ring at position 5 or atom C2. The bond distances agree with the literature values (Allen et al., 1987) and are comparable with the related structures (Al-Abdullah et al., 2012; El-Emam et al., 2012; Fun et al., 2011).
In the crystal packing (Fig. 2), the molecules are linked into chains along the a axis by weak C—H···N interactions (Table 1). The crystal is further stabilized by weak C—H···π interactions (Table 1).