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Acta Cryst. (2011). E67, o463-o464    [ doi:10.1107/S1600536811002170 ]

3-Isobutyl-4-phenylsulfanyl-1H-pyrazol-5-ol

T. Shahani, H.-K. Fun, R. V. Ragavan, V. Vijayakumar and S. Sarveswari

Abstract top

The asymmetric unit of the title compound, C13H16N2OS, contains two independent molecules (A and B). The pyrazole ring [maximum deviations = 0.0049 (17) Å in molecule A and 0.0112 (19) Å in molecule B] makes a dihedral angle of 70.23 (11) and 73.18 (12)° with the phenyl ring in molecules A and B, respectively. The isobutyl group in molecule B is disordered over two sets of sites with a ratio of refined occupancies of 0.858 (5):0.142 (5). In the crystal, molecules A and B are linked via a pair of intermolecular N-H...O hydrogen bonds, generating an R22(8) ring motif. These ring motifs are further linked into two-dimensional arrays parallel to the bc plane by intermolecular N-H...O and weak C-H...S hydrogen bonds. The crystal is further stablized by weak [pi]-[pi] interactions [centroid-centroid distances = 3.5698 (13) and 3.5287 (12) Å].

Comment top

Antibacterial and antifungal activities of the azoles are most widely studied and some of them are in clinical practice as anti-microbial agents. However, the azole-resistant strain had led to the development of new antimicrobial compounds. In particular pyrazole derivatives are extensively studied and used as antimicrobial agents. Pyrazole is an important class of heterocyclic compounds and many pyrazole derivatives are reported to have the broad spectrum of biological properties such as anti-inflammatory, antifungal, herbicidal, anti-tumour, cytotoxic, molecular modelling, and antiviral activities. Pyrazole derivatives also act as antiangiogenic agents, A3 adenosine receptor antagonists, neuropeptide YY5 receptor antagonists, kinase inhibitor for treatment of type 2 diabetes, hyperlipidemia, obesity, and thrombopiotinmimetics. Recently urea derivatives of pyrazoles have been reported as potent inhibitors of p38 kinase. Since the high electronegativity of halogens (particularly chlorine and fluorine) in the aromatic part of the drug molecules play an important role in enhancing their biological activity, we are interested to have 4-fluoro or 4-chloro substitution in the aryls of 1,5-diaryl pyrazoles. As part of our on-going research aiming the synthesis of new antimicrobial compounds, we have reported the synthesis of novel pyrazole derivatives and their microbial activities (Ragavan et al., 2009; 2010). The structure of the title compound is presented here.

In the asymmetric unit of the title compound, (Fig. 1), the 1H-pyrazol ring (N1/N2/C7–C9) in molecule A (with maximum deviation of 0.0049 (17) Å at atom N2A) makes dihedral angle of 70.23 (11)° with phenyl ring (C1–C6). The corresponding values in molecule B are maximum deviation of 0.0112 (19) Å at atom N2B and 73.18 (12)°. The torsion angles of O1/C7/C8/S1 are 5.8 (3) and 7.0 (3)° in molecules A and B, respectively. The isobutane moiety (C10–C13) in molecule B is disordered over two positions with refined site-occupancies of 0.858 (5): 0.142 (5). The bond lengths (Allen et al.,1987) and angles are within normal ranges and comparable to those closely related structures (Shahani et al.,2009; 2010a, b, c).

In the crystal packing (Fig. 2), pairs of intermolecular N2A—H2NA···O1B and N2B—H2NB···O1A hydrogen bonds link neighbouring molecules, generating R22(8) ring motifs (Bernstein et al., 1995). Furthermore, N1A—H1NA···O1Ai, N1B—H1NB···O1Bii and C10B—H10D···S1Aiii hydrogen bonds (see Table 1 for symmetry codes) link the molecules into two-dimensional arrays parallel to the bc plane. The crystal structure is stablilized by weak π–π interactions [Cg1···Cg2 = 3.5698 (13) Å, symmetry code, 1/2-x, -1/2+y, z and Cg3···Cg4 = 3.5287 (12) Å, symmetry code, 1/2-x, 1/2+y, z]. Cg1 and Cg3 are the centroids of the 1H-pyrazole rings (N1B/N2B/C7B–C9B and N1A/N2A/C7A–C9A), Cg2 and Cg4 are the centroids of benzene rings (C1B–C6B and C1A–C6A).

Related literature top

For pyrazole derivatives and their microbial activity, see: Ragavan et al. (2009, 2010). For related structures, see: Shahani et al. (2009, 2010a,b,c). For hydrogen-bond motifs, see: Bernstein et al. (1995). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

The compound was synthesized using the method available in the literature (Ragavan et al.,2009) and recrystallized using the ethanol-chloroform 1:1 mixture. Yield: 71%. Mp: 489 K.

Refinement top

The hydrogen atoms bound to C atoms were positioned geometrically [C–H = 0.93–0.98 Å] with Uiso(H) =1.2 or 1.5Uiso(C). The hydrogen atoms attached to the N atoms were located from the difference map and refined freely, [N–H = 0.84 (3)—0.95 (3) Å]. The isobutane moiety (C10–C13) in molecule B is disordered over two positions with refined site-occupancies of 0.858 (5): 0.142 (5). The same Uij parameters were used for atom pair C11B and C11C.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. The open bonds indicate the minor component of disorder.
[Figure 2] Fig. 2. The crystal packing of the title compound, showing a two-dimensional array parallel to the bc plane. Intermolecular hydrogen bonds are shown as dashed lines.
3-Isobutyl-4-phenylsulfanyl-1H-pyrazol-5-ol top
Crystal data top
C13H16N2OSF(000) = 2112
Mr = 248.34Dx = 1.234 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 4628 reflections
a = 20.7342 (6) Åθ = 2.6–29.7°
b = 11.1320 (3) ŵ = 0.23 mm−1
c = 23.1608 (6) ÅT = 100 K
V = 5345.8 (3) Å3Block, colourless
Z = 160.37 × 0.24 × 0.14 mm
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		7837 independent reflections
Radiation source: fine-focus sealed tube5405 reflections with I > 2σ(I)
graphiteRint = 0.066
φ and ω scansθmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −25→29
Tmin = 0.920, Tmax = 0.969k = −14→15
33422 measured reflectionsl = −31→32
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0338P)2 + 4.0215P]
where P = (Fo2 + 2Fc2)/3
7837 reflections(Δ/σ)max < 0.001
329 parametersΔρmax = 0.57 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C13H16N2OSV = 5345.8 (3) Å3
Mr = 248.34Z = 16
Orthorhombic, PbcnMo Kα radiation
a = 20.7342 (6) ŵ = 0.23 mm−1
b = 11.1320 (3) ÅT = 100 K
c = 23.1608 (6) Å0.37 × 0.24 × 0.14 mm
Data collection top
Bruker APEXII DUO CCD area-detector
diffractometer		7837 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		5405 reflections with I > 2σ(I)
Tmin = 0.920, Tmax = 0.969Rint = 0.066
33422 measured reflectionsθmax = 30.1°
Refinement top
R[F2 > 2σ(F2)] = 0.062H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131Δρmax = 0.57 e Å−3
S = 1.14Δρmin = −0.36 e Å−3
7837 reflectionsAbsolute structure: ?
329 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.19888 (3)0.02166 (5)0.45317 (2)0.01991 (12)
O1A0.28838 (7)0.04530 (12)0.33405 (6)0.0167 (3)
N1A0.21490 (8)0.31619 (16)0.36323 (7)0.0166 (4)
N2A0.25553 (8)0.24348 (15)0.33265 (8)0.0154 (3)
C1A0.13701 (11)−0.19063 (19)0.44122 (10)0.0229 (5)
H1AA0.1514−0.20440.47870.028*
C2A0.10188 (12)−0.2778 (2)0.41238 (11)0.0294 (5)
H2AA0.0922−0.34970.43090.035*
C3A0.08107 (11)−0.2593 (2)0.35642 (12)0.0319 (6)
H3AA0.0584−0.31920.33710.038*
C4A0.09414 (11)−0.1515 (2)0.32926 (11)0.0283 (5)
H4AA0.0797−0.13860.29180.034*
C5A0.12885 (10)−0.0618 (2)0.35763 (10)0.0216 (5)
H5AA0.13730.01080.33920.026*
C6A0.15065 (10)−0.08166 (18)0.41356 (9)0.0189 (4)
C7A0.25607 (10)0.13164 (17)0.35621 (8)0.0151 (4)
C8A0.21390 (10)0.13713 (17)0.40444 (9)0.0164 (4)
C9A0.18970 (10)0.25375 (18)0.40703 (9)0.0177 (4)
C10A0.14148 (11)0.30870 (19)0.44681 (9)0.0222 (5)
H10A0.14790.39500.44770.027*
H10B0.14860.27830.48550.027*
C11A0.07172 (11)0.2821 (2)0.42884 (11)0.0274 (5)
H11A0.06590.19470.42830.033*
C12A0.02496 (13)0.3346 (3)0.47288 (13)0.0447 (7)
H12A0.03480.30340.51050.067*
H12B−0.01840.31310.46260.067*
H12C0.02900.42050.47330.067*
C13A0.05691 (13)0.3300 (3)0.36880 (12)0.0443 (7)
H13A0.01220.31660.36010.066*
H13B0.08320.28900.34090.066*
H13C0.06600.41450.36750.066*
S1B0.20246 (3)0.30672 (5)0.09810 (2)0.02120 (13)
O1B0.28972 (7)0.28861 (12)0.21994 (6)0.0168 (3)
N1B0.21814 (8)0.01560 (16)0.19109 (7)0.0166 (4)
N2B0.25850 (9)0.08975 (15)0.22121 (8)0.0168 (4)
C1B0.12469 (11)0.3859 (2)0.18971 (11)0.0252 (5)
H1BA0.13240.31290.20800.030*
C2B0.08736 (11)0.4730 (2)0.21669 (12)0.0316 (6)
H2BA0.07030.45820.25310.038*
C3B0.07542 (12)0.5817 (2)0.18976 (13)0.0364 (6)
H3BA0.05100.64010.20830.044*
C4B0.09985 (14)0.6030 (2)0.13543 (13)0.0405 (7)
H4BA0.09100.67540.11710.049*
C5B0.13763 (12)0.5173 (2)0.10778 (11)0.0320 (6)
H5BA0.15430.53260.07120.038*
C6B0.15048 (11)0.40805 (19)0.13536 (10)0.0217 (5)
C7B0.25854 (10)0.20082 (18)0.19731 (8)0.0155 (4)
C8B0.21715 (10)0.19358 (18)0.14830 (9)0.0166 (4)
C9B0.19360 (10)0.07625 (18)0.14657 (9)0.0176 (4)
C10B0.14766 (10)0.0172 (2)0.10600 (9)0.0218 (4)
H10C0.1516−0.06840.11000.026*0.858 (5)
H10D0.15960.03780.06720.026*0.858 (5)
H10E0.1699−0.04900.08840.026*0.142 (5)
H10F0.13790.07360.07590.026*0.142 (5)
C11B0.07762 (13)0.0524 (3)0.11539 (12)0.0241 (6)0.858 (5)
H11B0.07350.13830.10690.029*0.858 (5)
C11C0.0867 (8)−0.0274 (16)0.1281 (7)0.0241 (6)0.142 (5)
H11C0.0919−0.11250.13790.029*0.142 (5)
C12B0.03645 (12)−0.0169 (3)0.07140 (12)0.0436 (7)
H12D−0.00810.00410.07620.065*0.858 (5)
H12E0.05010.00330.03300.065*0.858 (5)
H12F0.0418−0.10160.07760.065*0.858 (5)
H12G0.0557−0.05420.03820.065*0.142 (5)
H12H−0.0033−0.05670.08050.065*0.142 (5)
H12I0.02810.06620.06320.065*0.142 (5)
C13B0.05389 (14)0.0320 (3)0.17556 (12)0.0466 (8)
H13D0.08010.07630.20230.070*0.858 (5)
H13E0.00990.05810.17870.070*0.858 (5)
H13F0.0566−0.05210.18420.070*0.858 (5)
H13G0.08060.02890.20940.070*0.142 (5)
H13H0.04540.11430.16580.070*0.142 (5)
H13I0.0139−0.00860.18310.070*0.142 (5)
H1NA0.2143 (13)0.399 (3)0.3566 (12)0.040 (8)*
H2NA0.2738 (11)0.267 (2)0.2993 (11)0.021 (6)*
H1NB0.2156 (14)−0.068 (3)0.2000 (12)0.044 (8)*
H2NB0.2737 (12)0.066 (2)0.2531 (11)0.024 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0318 (3)0.0154 (2)0.0125 (2)−0.0018 (2)0.0023 (2)0.00261 (19)
O1A0.0226 (7)0.0114 (7)0.0162 (7)0.0012 (6)0.0019 (6)−0.0002 (5)
N1A0.0223 (9)0.0110 (8)0.0166 (8)0.0014 (7)0.0013 (7)0.0003 (6)
N2A0.0204 (9)0.0111 (8)0.0147 (8)−0.0002 (7)0.0040 (7)−0.0004 (6)
C1A0.0306 (12)0.0164 (10)0.0218 (11)−0.0001 (9)0.0074 (9)0.0020 (8)
C2A0.0291 (12)0.0181 (11)0.0412 (15)−0.0059 (9)0.0108 (11)0.0011 (10)
C3A0.0224 (12)0.0248 (12)0.0486 (16)−0.0064 (10)0.0006 (11)−0.0074 (11)
C4A0.0229 (12)0.0302 (13)0.0317 (13)0.0015 (10)−0.0046 (10)−0.0034 (10)
C5A0.0216 (11)0.0198 (10)0.0235 (11)0.0003 (8)0.0020 (9)0.0028 (8)
C6A0.0205 (10)0.0166 (10)0.0196 (10)0.0005 (8)0.0064 (8)0.0002 (8)
C7A0.0212 (10)0.0111 (9)0.0131 (9)−0.0018 (8)−0.0023 (8)0.0000 (7)
C8A0.0237 (10)0.0111 (9)0.0143 (9)−0.0008 (8)0.0006 (8)0.0005 (7)
C9A0.0231 (10)0.0152 (9)0.0147 (10)−0.0017 (8)0.0010 (8)0.0000 (8)
C10A0.0306 (12)0.0176 (10)0.0183 (10)0.0028 (9)0.0060 (9)−0.0027 (8)
C11A0.0287 (12)0.0249 (12)0.0286 (13)−0.0006 (10)0.0076 (10)−0.0014 (10)
C12A0.0349 (15)0.0530 (18)0.0464 (17)0.0089 (13)0.0163 (13)−0.0037 (14)
C13A0.0295 (14)0.068 (2)0.0352 (16)0.0052 (14)−0.0014 (12)0.0024 (15)
S1B0.0310 (3)0.0189 (3)0.0137 (2)0.0003 (2)−0.0030 (2)0.00392 (19)
O1B0.0238 (8)0.0116 (6)0.0149 (7)−0.0019 (6)−0.0016 (6)−0.0007 (5)
N1B0.0235 (9)0.0116 (8)0.0147 (8)−0.0020 (7)−0.0030 (7)−0.0019 (7)
N2B0.0240 (9)0.0127 (8)0.0137 (8)−0.0005 (7)−0.0039 (7)0.0004 (6)
C1B0.0217 (11)0.0213 (11)0.0324 (13)0.0004 (9)−0.0028 (10)0.0035 (10)
C2B0.0233 (12)0.0331 (14)0.0385 (14)0.0029 (10)0.0002 (10)−0.0018 (11)
C3B0.0278 (13)0.0318 (14)0.0496 (17)0.0116 (11)−0.0088 (12)−0.0068 (12)
C4B0.0466 (16)0.0216 (12)0.0532 (19)0.0102 (12)−0.0217 (14)0.0029 (12)
C5B0.0409 (14)0.0241 (12)0.0311 (13)0.0023 (11)−0.0128 (11)0.0050 (10)
C6B0.0235 (11)0.0182 (10)0.0235 (11)0.0007 (9)−0.0091 (9)0.0012 (8)
C7B0.0199 (10)0.0136 (9)0.0130 (9)0.0024 (8)0.0017 (8)0.0006 (7)
C8B0.0232 (10)0.0138 (9)0.0130 (9)0.0005 (8)−0.0006 (8)0.0008 (7)
C9B0.0219 (10)0.0165 (9)0.0143 (9)0.0014 (8)0.0017 (8)−0.0028 (8)
C10B0.0257 (11)0.0221 (11)0.0177 (10)−0.0022 (9)−0.0032 (9)−0.0051 (9)
C11B0.0246 (13)0.0244 (14)0.0233 (13)−0.0004 (11)−0.0021 (11)−0.0031 (11)
C11C0.0246 (13)0.0244 (14)0.0233 (13)−0.0004 (11)−0.0021 (11)−0.0031 (11)
C12B0.0267 (13)0.075 (2)0.0294 (14)−0.0107 (14)−0.0032 (11)−0.0126 (14)
C13B0.0339 (15)0.074 (2)0.0314 (15)−0.0169 (15)0.0063 (12)−0.0169 (15)
Geometric parameters (Å, °) top
S1A—C8A1.739 (2)C1B—C2B1.389 (3)
S1A—C6A1.779 (2)C1B—C6B1.390 (3)
O1A—C7A1.279 (2)C1B—H1BA0.9300
N1A—C9A1.336 (3)C2B—C3B1.383 (4)
N1A—N2A1.366 (2)C2B—H2BA0.9300
N1A—H1NA0.94 (3)C3B—C4B1.377 (4)
N2A—C7A1.359 (2)C3B—H3BA0.9300
N2A—H2NA0.90 (2)C4B—C5B1.390 (4)
C1A—C2A1.385 (3)C4B—H4BA0.9300
C1A—C6A1.401 (3)C5B—C6B1.400 (3)
C1A—H1AA0.9300C5B—H5BA0.9300
C2A—C3A1.381 (4)C7B—C8B1.425 (3)
C2A—H2AA0.9300C8B—C9B1.395 (3)
C3A—C4A1.382 (3)C9B—C10B1.491 (3)
C3A—H3AA0.9300C10B—C11C1.451 (16)
C4A—C5A1.395 (3)C10B—C11B1.520 (3)
C4A—H4AA0.9300C10B—H10C0.9600
C5A—C6A1.390 (3)C10B—H10D0.9601
C5A—H5AA0.9300C10B—H10E0.9599
C7A—C8A1.420 (3)C10B—H10F0.9601
C8A—C9A1.393 (3)C11B—C13B1.495 (4)
C9A—C10A1.491 (3)C11B—C12B1.537 (4)
C10A—C11A1.534 (3)C11B—H10F1.5675
C10A—H10A0.9700C11B—H11B0.9800
C10A—H10B0.9700C11B—H13H1.5112
C11A—C13A1.520 (4)C11C—C13B1.452 (16)
C11A—C12A1.524 (3)C11C—C12B1.680 (16)
C11A—H11A0.9800C11C—H10C1.4813
C12A—H12A0.9600C11C—H11C0.9800
C12A—H12B0.9600C11C—H13F1.4689
C12A—H12C0.9600C12B—H12D0.9600
C13A—H13A0.9600C12B—H12E0.9600
C13A—H13B0.9600C12B—H12F0.9600
C13A—H13C0.9600C12B—H12G0.9599
S1B—C8B1.741 (2)C12B—H12H0.9600
S1B—C6B1.783 (2)C12B—H12I0.9601
O1B—C7B1.284 (2)C13B—H13D0.9602
N1B—C9B1.333 (3)C13B—H13E0.9600
N1B—N2B1.367 (2)C13B—H13F0.9598
N1B—H1NB0.95 (3)C13B—H13G0.9602
N2B—C7B1.355 (3)C13B—H13H0.9602
N2B—H2NB0.84 (3)C13B—H13I0.9598
C8A—S1A—C6A104.12 (10)C11C—C10B—H10C72.6
C9A—N1A—N2A109.06 (17)C9B—C10B—H10C108.8
C9A—N1A—H1NA129.2 (17)C11B—C10B—H10C108.9
N2A—N1A—H1NA120.6 (17)C11C—C10B—H10D129.5
C7A—N2A—N1A109.86 (17)C9B—C10B—H10D108.7
C7A—N2A—H2NA127.7 (15)C11B—C10B—H10D108.6
N1A—N2A—H2NA121.9 (15)H10C—C10B—H10D107.8
C2A—C1A—C6A119.5 (2)C11C—C10B—H10E107.9
C2A—C1A—H1AA120.3C9B—C10B—H10E107.4
C6A—C1A—H1AA120.3C11B—C10B—H10E135.9
C3A—C2A—C1A120.8 (2)H10D—C10B—H10E70.2
C3A—C2A—H2AA119.6C11C—C10B—H10F107.3
C1A—C2A—H2AA119.6C9B—C10B—H10F107.7
C2A—C3A—C4A119.7 (2)C11B—C10B—H10F74.6
C2A—C3A—H3AA120.2H10C—C10B—H10F137.4
C4A—C3A—H3AA120.2H10E—C10B—H10F107.1
C3A—C4A—C5A120.6 (2)C13B—C11B—C10B114.1 (2)
C3A—C4A—H4AA119.7C13B—C11B—C12B111.0 (2)
C5A—C4A—H4AA119.7C10B—C11B—C12B107.8 (2)
C6A—C5A—C4A119.5 (2)C13B—C11B—H10F146.1
C6A—C5A—H5AA120.2C12B—C11B—H10F97.6
C4A—C5A—H5AA120.2C13B—C11B—H11B107.9
C5A—C6A—C1A119.9 (2)C10B—C11B—H11B107.9
C5A—C6A—S1A124.09 (16)C12B—C11B—H11B107.9
C1A—C6A—S1A115.95 (17)H10F—C11B—H11B78.8
O1A—C7A—N2A122.10 (18)C10B—C11B—H13H130.6
O1A—C7A—C8A132.11 (18)C12B—C11B—H13H119.7
N2A—C7A—C8A105.74 (17)H10F—C11B—H13H137.3
C9A—C8A—C7A107.20 (17)H11B—C11B—H13H70.8
C9A—C8A—S1A126.62 (16)C10B—C11C—C13B121.3 (11)
C7A—C8A—S1A126.10 (15)C10B—C11C—C12B104.0 (10)
N1A—C9A—C8A108.13 (18)C13B—C11C—C12B105.6 (10)
N1A—C9A—C10A121.20 (18)C13B—C11C—H10C141.3
C8A—C9A—C10A130.58 (19)C12B—C11C—H10C111.3
C9A—C10A—C11A112.67 (18)C10B—C11C—H11C108.4
C9A—C10A—H10A109.1C13B—C11C—H11C108.4
C11A—C10A—H10A109.1C12B—C11C—H11C108.4
C9A—C10A—H10B109.1H10C—C11C—H11C70.6
C11A—C10A—H10B109.1C10B—C11C—H13F138.3
H10A—C10A—H10B107.8C12B—C11C—H13F116.2
C13A—C11A—C12A110.4 (2)H10C—C11C—H13F125.4
C13A—C11A—C10A111.8 (2)H11C—C11C—H13F70.1
C12A—C11A—C10A110.1 (2)C11B—C12B—H12D109.7
C13A—C11A—H11A108.1C11C—C12B—H12D121.6
C12A—C11A—H11A108.1C11B—C12B—H12E109.5
C10A—C11A—H11A108.1C11C—C12B—H12E123.9
C11A—C12A—H12A109.5H12D—C12B—H12E109.5
C11A—C12A—H12B109.5C11B—C12B—H12F109.3
H12A—C12A—H12B109.5C11C—C12B—H12F75.2
C11A—C12A—H12C109.5H12D—C12B—H12F109.5
H12A—C12A—H12C109.5H12E—C12B—H12F109.5
H12B—C12A—H12C109.5C11B—C12B—H12G121.1
C11A—C13A—H13A109.5C11C—C12B—H12G109.7
C11A—C13A—H13B109.5H12D—C12B—H12G126.7
H13A—C13A—H13B109.5H12F—C12B—H12G69.3
C11A—C13A—H13C109.5C11B—C12B—H12H124.3
H13A—C13A—H13C109.5C11C—C12B—H12H109.2
H13B—C13A—H13C109.5H12E—C12B—H12H124.4
C8B—S1B—C6B103.90 (10)H12F—C12B—H12H67.2
C9B—N1B—N2B108.82 (17)H12G—C12B—H12H109.5
C9B—N1B—H1NB129.8 (18)C11B—C12B—H12I75.4
N2B—N1B—H1NB120.7 (17)C11C—C12B—H12I109.5
C7B—N2B—N1B110.06 (17)H12D—C12B—H12I67.3
C7B—N2B—H2NB130.0 (17)H12E—C12B—H12I69.2
N1B—N2B—H2NB119.0 (17)H12F—C12B—H12I175.2
C2B—C1B—C6B119.9 (2)H12G—C12B—H12I109.5
C2B—C1B—H1BA120.1H12H—C12B—H12I109.5
C6B—C1B—H1BA120.1C11C—C13B—H13D117.2
C3B—C2B—C1B120.5 (3)C11B—C13B—H13D109.7
C3B—C2B—H2BA119.8C11C—C13B—H13E129.8
C1B—C2B—H2BA119.8C11B—C13B—H13E109.8
C4B—C3B—C2B119.8 (2)H13D—C13B—H13E109.5
C4B—C3B—H3BA120.1C11C—C13B—H13F71.7
C2B—C3B—H3BA120.1C11B—C13B—H13F108.9
C3B—C4B—C5B120.7 (2)H13D—C13B—H13F109.5
C3B—C4B—H4BA119.7H13E—C13B—H13F109.5
C5B—C4B—H4BA119.7C11C—C13B—H13G109.3
C4B—C5B—C6B119.5 (3)C11B—C13B—H13G125.2
C4B—C5B—H5BA120.2H13E—C13B—H13G119.8
C6B—C5B—H5BA120.2H13F—C13B—H13G76.2
C1B—C6B—C5B119.6 (2)C11C—C13B—H13H110.0
C1B—C6B—S1B123.98 (17)C11B—C13B—H13H72.3
C5B—C6B—S1B116.37 (19)H13D—C13B—H13H76.5
O1B—C7B—N2B121.90 (18)H13E—C13B—H13H63.6
O1B—C7B—C8B132.18 (18)H13F—C13B—H13H172.5
N2B—C7B—C8B105.87 (18)H13G—C13B—H13H109.5
C9B—C8B—C7B106.66 (18)C11C—C13B—H13I109.1
C9B—C8B—S1B126.65 (16)C11B—C13B—H13I121.7
C7B—C8B—S1B126.60 (16)H13D—C13B—H13I127.8
N1B—C9B—C8B108.55 (18)H13E—C13B—H13I46.2
N1B—C9B—C10B120.52 (18)H13F—C13B—H13I63.4
C8B—C9B—C10B130.91 (19)H13G—C13B—H13I109.5
C11C—C10B—C9B119.0 (6)H13H—C13B—H13I109.5
C9B—C10B—C11B113.98 (18)
C9A—N1A—N2A—C7A1.0 (2)C4B—C5B—C6B—S1B−177.12 (19)
C6A—C1A—C2A—C3A1.1 (3)C8B—S1B—C6B—C1B−6.3 (2)
C1A—C2A—C3A—C4A−1.5 (4)C8B—S1B—C6B—C5B171.51 (18)
C2A—C3A—C4A—C5A0.8 (4)N1B—N2B—C7B—O1B175.70 (18)
C3A—C4A—C5A—C6A0.3 (3)N1B—N2B—C7B—C8B−1.9 (2)
C4A—C5A—C6A—C1A−0.8 (3)O1B—C7B—C8B—C9B−176.2 (2)
C4A—C5A—C6A—S1A176.58 (17)N2B—C7B—C8B—C9B1.0 (2)
C2A—C1A—C6A—C5A0.1 (3)O1B—C7B—C8B—S1B7.0 (3)
C2A—C1A—C6A—S1A−177.48 (17)N2B—C7B—C8B—S1B−175.73 (16)
C8A—S1A—C6A—C5A−3.8 (2)C6B—S1B—C8B—C9B108.8 (2)
C8A—S1A—C6A—C1A173.60 (16)C6B—S1B—C8B—C7B−75.1 (2)
N1A—N2A—C7A—O1A177.07 (18)N2B—N1B—C9B—C8B−1.4 (2)
N1A—N2A—C7A—C8A−0.8 (2)N2B—N1B—C9B—C10B180.00 (18)
O1A—C7A—C8A—C9A−177.2 (2)C7B—C8B—C9B—N1B0.3 (2)
N2A—C7A—C8A—C9A0.3 (2)S1B—C8B—C9B—N1B176.98 (16)
O1A—C7A—C8A—S1A5.8 (3)C7B—C8B—C9B—C10B178.6 (2)
N2A—C7A—C8A—S1A−176.61 (15)S1B—C8B—C9B—C10B−4.7 (3)
C6A—S1A—C8A—C9A110.8 (2)N1B—C9B—C10B—C11C61.5 (9)
C6A—S1A—C8A—C7A−72.8 (2)C8B—C9B—C10B—C11C−116.7 (8)
N2A—N1A—C9A—C8A−0.8 (2)N1B—C9B—C10B—C11B103.1 (2)
N2A—N1A—C9A—C10A−177.72 (18)C8B—C9B—C10B—C11B−75.1 (3)
C7A—C8A—C9A—N1A0.3 (2)C11C—C10B—C11B—C13B51.9 (10)
S1A—C8A—C9A—N1A177.18 (16)C9B—C10B—C11B—C13B−55.2 (3)
C7A—C8A—C9A—C10A176.8 (2)C11C—C10B—C11B—C12B−72.0 (10)
S1A—C8A—C9A—C10A−6.3 (3)C9B—C10B—C11B—C12B−179.0 (2)
N1A—C9A—C10A—C11A94.6 (2)C9B—C10B—C11C—C13B32.4 (16)
C8A—C9A—C10A—C11A−81.6 (3)C11B—C10B—C11C—C13B−59.8 (11)
C9A—C10A—C11A—C13A−60.0 (3)C9B—C10B—C11C—C12B150.8 (5)
C9A—C10A—C11A—C12A176.9 (2)C11B—C10B—C11C—C12B58.6 (9)
C9B—N1B—N2B—C7B2.1 (2)C13B—C11B—C12B—C11C−63.0 (10)
C6B—C1B—C2B—C3B0.2 (4)C10B—C11B—C12B—C11C62.7 (10)
C1B—C2B—C3B—C4B1.0 (4)C10B—C11C—C12B—C11B−65.9 (10)
C2B—C3B—C4B—C5B−1.4 (4)C13B—C11C—C12B—C11B62.8 (9)
C3B—C4B—C5B—C6B0.5 (4)C10B—C11C—C13B—C11B60.7 (12)
C2B—C1B—C6B—C5B−1.1 (3)C12B—C11C—C13B—C11B−56.9 (8)
C2B—C1B—C6B—S1B176.58 (18)C10B—C11B—C13B—C11C−51.2 (10)
C4B—C5B—C6B—C1B0.8 (3)C12B—C11B—C13B—C11C70.9 (10)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1Ai0.94 (3)1.71 (3)2.639 (2)171 (3)
N2A—H2NA···O1B0.90 (2)1.88 (3)2.752 (2)161 (2)
N1B—H1NB···O1Bii0.95 (3)1.67 (3)2.619 (2)176 (3)
N2B—H2NB···O1A0.85 (3)1.91 (3)2.731 (2)162 (2)
C10B—H10D···S1Aiii0.962.843.721 (2)153
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z; (iii) x, −y, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···O1Ai0.94 (3)1.71 (3)2.639 (2)171 (3)
N2A—H2NA···O1B0.90 (2)1.88 (3)2.752 (2)161 (2)
N1B—H1NB···O1Bii0.95 (3)1.67 (3)2.619 (2)176 (3)
N2B—H2NB···O1A0.85 (3)1.91 (3)2.731 (2)162 (2)
C10B—H10D···S1Aiii0.962.843.721 (2)153
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z; (iii) x, −y, z−1/2.
Acknowledgements top

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

references
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