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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 4| April 2013| Pages o491-o492

2-Amino-6-methyl-5-{5-[(naphthalen-2-yl­­oxy)meth­yl]-1,3,4-oxa­diazol-2-ylsulfan­yl}-4-(3-nitro­phen­yl)pyridine-3-carbo­nitrile

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, and cDepartment of studies in Chemistry, Mangalore University, Mangalagangothri 574 199, India
*Correspondence e-mail: hkfun@usm.my

(Received 20 February 2013; accepted 28 February 2013; online 6 March 2013)

The asymmetric unit of the title compound, C26H18N6O4S, contains two independent mol­ecules (A and B). The dihedral angles between the oxadiazole ring and naphthalene ring system are 42.59 (14) and 6.88 (14) Å in mol­ecules A and B, respectively. The dihedral angles between the pyridine and benzene rings in A and B are 65.53 (13 )and 87.67 (13) Å, respectively. In the crystal, mol­ecules A and B are linked through a pair of N—H⋯N hydrogen bonds involving one -NH2 group H atom and second pair of N—H⋯N hydrogen bonds involving the other -NH2 group H atom, forming an –ABAB– ribbon along [100] containing R22(8) and R22(12) ring motifs. These ribbons are further connected by weak C—H⋯N, C—H⋯O and C—H⋯π inter­actions, resulting in a three-dimensional network. The crystal studied was a non-merohedral twin with refined components 0.906 (1):0.094 (1).

Related literature

For background to pyridine chemistry, see: Youngdale (1980[Youngdale, G. A. (1980). US Patent 4 288 440.], 1982[Youngdale, G. A. (1982). Chem. Abstr. 96, 6596.]); Todd (1970a[Todd, A. H. (1970a). UK Patent 1 203 149.],b[Todd, A. H. (1970b). Chem. Abstr. 73, 120509.]); Lohaus et al. (1968[Lohaus, G., Dittmar, W. & Afric, S. (1968). Pat. 6 906, 036.], 1970[Lohaus, G., Dittmar, W. & Afric, S. (1970). Chem. Abstr. 73, 120508.]); Gachet et al. (1995[Gachet, C., Cattanea, M., Ohlmann, P., Lecchi, B., Cassel, J., Mannucci, P. & Cazenave, J. P. (1995). Br. J. Haematol. 91, 434.]); Yao et al. (1994[Yao, S. K., Ober, J. C., Ferguson, J. J., Maffrand, J. P., Anderson, H. V., Buja, L. M. & Willerson, J. T. (1994). Am. J. Physiol. pp. H488-H493.]); Umemura et al. (1995[Umemura, K., Kawai, H., Ishihara, H. & Nakashima, M. (1995). Jpn J. Pharmacol. 76, 253-258.]). For background to 1,3,4-oxadiazole chemistry, see: Jin et al. (2006[Jin, L., Chen, J., Song, B., Chen, Z., Yang, S., Li, Q., Hu, D. & Xu, R. (2006). Bioorg. Med. Chem. Lett. 16, 5036-5040.]); Bhandari et al. (2008[Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822-1831.]); Krasovskii et al. (2000[Krasovskii, A. N., Bulgakov, A. K., Andrushko, A. P., Krasovskii, I. A., Dyachenko, A. M., Bokun, A. A., Kravchenko, N. A. & Demchenko, A. M. (2000). Pharm. Chem. J. 34, 115-117.]); Mishra et al. (1995[Mishra, L., Said, M. K., Itokawa, H. & Takeya, K. (1995). Bioorg. Med. Chem. Lett. 3, 1241-1245.]); Suman et al. (1979[Suman, S. P. & Bahel, S. C. V. (1979). J. Indian Chem. Soc. 56, 712.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C26H18N6O4S

  • Mr = 510.52

  • Triclinic, [P \overline 1]

  • a = 9.6132 (9) Å

  • b = 9.8928 (10) Å

  • c = 25.724 (2) Å

  • α = 83.215 (2)°

  • β = 84.102 (2)°

  • γ = 72.564 (2)°

  • V = 2311.8 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 100 K

  • 0.23 × 0.19 × 0.09 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.983

  • 9469 measured reflections

  • 9469 independent reflections

  • 8293 reflections with I > 2σ(I)

  • Rint = 0.000

Refinement
  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.164

  • S = 1.20

  • 9469 reflections

  • 686 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1B/C2B/C7B–C10B, C2B–C7B, C1A/C2A/C3A/C8A–C10A and O2A/C12A/N1A/N2A/C13A rings, respecively.

D—H⋯A D—H H⋯A DA D—H⋯A
N4A—H2NA⋯N5Bi 0.86 (4) 2.21 (4) 3.025 (4) 158 (3)
N4A—H1NA⋯N3Bii 0.84 (4) 2.23 (4) 3.056 (4) 165 (4)
N4B—H2NB⋯N3Aii 0.92 (4) 2.08 (4) 2.991 (4) 174 (4)
N4B—H1NB⋯N5Ai 0.85 (5) 2.34 (5) 3.157 (4) 162 (4)
C11A—H11B⋯O1Biii 0.99 2.36 3.332 (4) 168
C11B—H11C⋯O3Biv 0.99 2.60 3.173 (4) 117
C21B—H21B⋯N2Av 0.95 2.54 3.333 (4) 142
C22A—H22A⋯N1Bvi 0.95 2.60 3.540 (4) 169
C2A—H2AACg1vi 0.95 2.78 3.492 (3) 133
C4A—H4AACg2vi 0.95 2.62 3.457 (4) 147
C7A—H7AACg1iii 0.95 2.80 3.557 (3) 138
C3B—H3BACg3vii 0.95 2.67 3.440 (3) 138
C8B—H8BACg3viii 0.95 2.83 3.599 (3) 139
C24A—H24ACg4 0.95 2.92 3.652 (3) 135
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x, -y+2, -z; (iii) x, y-1, z; (iv) x-1, y, z; (v) x+1, y, z; (vi) x+1, y-1, z; (vii) -x, -y+1, -z+1; (viii) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Pyridine and its derivatives are of commercial interest and find application in medicinal drugs and in agricultural products such as herbicides,insecticides, fungicides, and plant growth regulators (picolines, lutidines, Timoprazole, and omeprazole). Pyridine derivatives have a wide range of biological activities being used as fungicidal, antibacterial, antifungal (Youngdale, 1980, 1982; Todd, 1970a,b), antimycotic (Lohaus et al., 1968, 1970) and antidepressant agents (Gachet et al., 1995), as well as thienopyridines being used as antithrombotic agents (Yao et al., 1994; Umemura et al., 1995) against platelet aggregation. Compounds containing a 1,3,4-oxadiazole ring have been reported to possess a broad spectrum of biological activities including insecticidal, antibacterial, anticancer, and anti-inflammatory (Jin et al., 2006; Bhandari et al., 2008; Krasovskii et al., 2000) as well as antimycobacterial, analgesic, antipyretic and anticonvulsant properties (Mishra et al., 1995; Suman et al., 1979). The above observations prompted us to synthesize the title compound containing oxadiazole and amino pyridine carbonitrile groups and substituted pyridine scaffolds to determine its crystal structure.

The asymmetric unit of the title compound consists of two crystallographically independent, 5-(5-((naphthalen-6-yloxy)methyl)-1,3,4-oxadiazol-2-ylthio) -2-amino-6-methyl-4-(3-nitrophenyl)pyridine-3-carbonitrile molecules (A & B), as shown in Fig. 1. The bond lengths and angles of molecules A and B agree with each other and are within normal ranges for bond lengths (Allen et al., 1987). The dihedral angles between pyridine rings (N3A/C14A–C18A)/ (N3B/C14B–C18B) and the benzene rings (C19A–C24A)/(C19B–C24B) are 65.53 (13) and 87.67 (13) Å, respectively. The central 1,3,4-oxadiazole ring system in both the molecules is essentially planar with maximum deviations of 0.007 (3) and 0.002 (3) %A respectively.

In the crystal structure (Fig. 2), molecule A is paired with molecule B via an N4—H···N3ii hydrogen bonds (symmetry code in Table 1), involving the 4-amino group and the pyridine N1 atom and it is paired with another molecule of B through a pair N4—H···N5i hydrogen bonds (symmetry code in Table 1), involving the 4-amino group and cyano N5 atom, forming R22(8) and R22(12) (Bernstein et al., 1995) ring motifs. These hydrogen-bonded ABAB pairs lead to a extended ribbon structure. Theese ribbon are linked by weak C—H···N, C—H···O hydrogen bonds, resulting in a three-dimensional network. The crystal structure is further stabilized by C—H···π interactions (Table 1).

Related literature top

For background to pyridine chemistry, see: Youngdale (1980, 1982); Todd (1970a,b); Lohaus et al. (1968, 1970); Gachet et al. (1995); Yao et al. (1994); Umemura et al. (1995). For background to 1,3,4-oxadiazole chemistry, see: Jin et al. (2006); Bhandari et al. (2008); Krasovskii et al. (2000); Mishra et al. (1995); Suman et al. (1979). 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 for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of malononitrile (10 mmol), substituted benzaldehyde (10 mmol), ammonium acetate (12.5 mmol) and 2-(5-((naphthalen-6-yloxy)methyl)-1,3,4-oxadiazol-2-ylthio)-1-(3-nitrophenyl)ethanone (8.33 mmol) in anhydrous benzene (25 ml) was refluxed for 18hrs, under nitrogen atm. Excess solvent was removed under reduced pressure. Residue was dissolved in ehtylacetate (50 ml) and washed successively with sodium bicarbonate solution (2 × 25 ml), water (2 × 25 ml), saturated brine solution (1 × 25 ml) and dried over anhydrous Na2SO4. Organic layer was evaporated to dryness and crude product was purified over silica using Dichloromethane/Methanol as eluent. Crystals suitable for X-ray studies were grown in a dimethylformamide solution (m.p:. 485 K).

Refinement top

N-bound H atoms were located in a difference Fourier map and were refined freely [refined N–H distance 0.86 (4), 0.84 (4), 0.92 (4) and 0.85 (4) Å]. The remaining hydrogen atoms were positioned geometrically [C–H = 0.95–0.99 Å] and were refined using a riding model, with Uiso(H) = 1.2 Ueq(C) or 1.5Ueq(methyl C). A rotating-group model was used for the methyl group. The crystal used was a non-merohedral twin with refined components 0.906 (1):0.094 (1). The structure was refined using the HKLF 5 type input.

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 asymmetric unit of the title compound with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.
2-Amino-6-methyl-5-{5-[(naphthalen-2-yloxy)methyl]-1,3,4-oxadiazol-2-ylsulfanyl}-4-(3-nitrophenyl)pyridine-3-carbonitrile top
Crystal data top
C26H18N6O4SZ = 4
Mr = 510.52F(000) = 1056
Triclinic, P1Dx = 1.467 Mg m3
Hall symbol: -P 1Melting point: 485 K
a = 9.6132 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.8928 (10) ÅCell parameters from 9913 reflections
c = 25.724 (2) Åθ = 2.2–31.8°
α = 83.215 (2)°µ = 0.19 mm1
β = 84.102 (2)°T = 100 K
γ = 72.564 (2)°Block, yellow
V = 2311.8 (4) Å30.23 × 0.19 × 0.09 mm
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
9469 independent reflections
Radiation source: fine-focus sealed tube8293 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
ϕ and ω scansθmax = 26.5°, θmin = 0.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1112
Tmin = 0.958, Tmax = 0.983k = 1212
9469 measured reflectionsl = 832
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.20 w = 1/[σ2(Fo2) + (0.0612P)2 + 3.203P]
where P = (Fo2 + 2Fc2)/3
9469 reflections(Δ/σ)max < 0.001
686 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C26H18N6O4Sγ = 72.564 (2)°
Mr = 510.52V = 2311.8 (4) Å3
Triclinic, P1Z = 4
a = 9.6132 (9) ÅMo Kα radiation
b = 9.8928 (10) ŵ = 0.19 mm1
c = 25.724 (2) ÅT = 100 K
α = 83.215 (2)°0.23 × 0.19 × 0.09 mm
β = 84.102 (2)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
9469 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
8293 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.983Rint = 0.000
9469 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0560 restraints
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.20Δρmax = 0.32 e Å3
9469 reflectionsΔρmin = 0.36 e Å3
686 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems 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*/Ueq
S1A0.16398 (8)0.33559 (7)0.14782 (3)0.02095 (16)
O1A0.2069 (2)0.3638 (3)0.35113 (8)0.0280 (5)
O2A0.1303 (2)0.3595 (2)0.25050 (8)0.0213 (4)
O3A0.5886 (3)0.4263 (4)0.30149 (11)0.0575 (8)
O4A0.3665 (3)0.5428 (3)0.28534 (9)0.0396 (6)
N1A0.0325 (3)0.5693 (3)0.25986 (10)0.0277 (6)
N2A0.0094 (3)0.5480 (3)0.20579 (10)0.0287 (6)
N3A0.0759 (3)0.6626 (3)0.03544 (9)0.0204 (5)
N4A0.2071 (3)0.8008 (3)0.01105 (10)0.0214 (5)
N5A0.5614 (3)0.6973 (3)0.03452 (11)0.0288 (6)
N6A0.4891 (3)0.4695 (3)0.27254 (11)0.0336 (6)
C1A0.3849 (3)0.2575 (3)0.41111 (12)0.0252 (6)
H1AA0.45610.24760.38220.030*
C2A0.4263 (3)0.2099 (3)0.46061 (13)0.0259 (6)
H2AA0.52670.16510.46580.031*
C3A0.3230 (3)0.2255 (3)0.50459 (12)0.0236 (6)
C4A0.3647 (4)0.1835 (3)0.55661 (13)0.0281 (7)
H4AA0.46490.14160.56290.034*
C5A0.2605 (4)0.2033 (3)0.59803 (13)0.0316 (7)
H5AA0.28950.17720.63290.038*
C6A0.1123 (4)0.2614 (3)0.58938 (13)0.0294 (7)
H6AA0.04120.27090.61830.035*
C7A0.0686 (3)0.3049 (3)0.53921 (12)0.0253 (6)
H7AA0.03240.34500.53380.030*
C8A0.1731 (3)0.2905 (3)0.49567 (12)0.0209 (6)
C9A0.1316 (3)0.3385 (3)0.44375 (12)0.0216 (6)
H9AA0.03160.38220.43750.026*
C10A0.2355 (3)0.3217 (3)0.40290 (12)0.0232 (6)
C11A0.0578 (3)0.4200 (3)0.34090 (12)0.0245 (6)
H11A0.01220.50590.35970.029*
H11B0.00500.34880.35310.029*
C12A0.0495 (3)0.4566 (3)0.28371 (11)0.0217 (6)
C13A0.0851 (3)0.4250 (3)0.20303 (11)0.0194 (6)
C14A0.1813 (3)0.4818 (3)0.10292 (11)0.0198 (6)
C15A0.0658 (3)0.5560 (3)0.07162 (11)0.0210 (6)
C16A0.2025 (3)0.6962 (3)0.02677 (10)0.0188 (5)
C17A0.3244 (3)0.6238 (3)0.05665 (11)0.0192 (6)
C18A0.3120 (3)0.5182 (3)0.09630 (10)0.0182 (5)
C19A0.4320 (3)0.4553 (3)0.13243 (11)0.0196 (6)
C20A0.5712 (3)0.3765 (3)0.11430 (13)0.0259 (6)
H20A0.59010.35770.07850.031*
C21A0.6824 (3)0.3254 (3)0.14864 (13)0.0290 (7)
H21A0.77640.27060.13610.035*
C22A0.6573 (3)0.3536 (3)0.20104 (14)0.0300 (7)
H22A0.73300.32010.22450.036*
C23A0.5191 (3)0.4318 (3)0.21772 (12)0.0252 (6)
C24A0.4061 (3)0.4836 (3)0.18467 (11)0.0205 (6)
H24A0.31220.53760.19760.025*
C25A0.0770 (3)0.5216 (4)0.07700 (13)0.0288 (7)
H25A0.14390.58700.05270.043*
H25B0.12000.53170.11310.043*
H25C0.06050.42350.06870.043*
C26A0.4569 (3)0.6636 (3)0.04550 (11)0.0213 (6)
S1B0.12684 (8)0.83421 (8)0.21600 (3)0.02183 (17)
O1B0.1561 (2)1.2195 (2)0.39059 (8)0.0265 (5)
O2B0.0028 (2)0.9464 (2)0.30307 (8)0.0208 (4)
O3B0.6655 (3)1.0426 (3)0.29656 (11)0.0454 (7)
O4B0.4448 (3)1.1689 (3)0.28241 (10)0.0377 (6)
N1B0.0584 (3)1.1801 (3)0.28436 (10)0.0276 (6)
N2B0.0113 (3)1.1138 (3)0.23840 (10)0.0262 (6)
N3B0.0583 (2)1.0526 (3)0.07428 (9)0.0192 (5)
N4B0.1950 (3)1.1622 (3)0.01522 (10)0.0247 (5)
N5B0.5528 (3)1.0738 (3)0.05879 (10)0.0270 (6)
N6B0.5503 (3)1.0651 (3)0.27607 (10)0.0266 (6)
C1B0.1881 (3)1.1234 (3)0.48129 (11)0.0206 (6)
H1BA0.14401.02820.47290.025*
C2B0.2398 (3)1.1516 (3)0.53383 (12)0.0212 (6)
C3B0.2306 (3)1.0404 (3)0.57422 (12)0.0230 (6)
H3BA0.18900.94470.56620.028*
C4B0.2807 (3)1.0679 (3)0.62501 (12)0.0256 (6)
H4BA0.27460.99160.65170.031*
C5B0.3413 (4)1.2102 (4)0.63744 (12)0.0291 (7)
H5BA0.37441.22950.67260.035*
C6B0.3525 (3)1.3201 (3)0.59898 (12)0.0265 (6)
H6BA0.39351.41520.60780.032*
C7B0.3041 (3)1.2946 (3)0.54617 (12)0.0225 (6)
C8B0.3159 (3)1.4046 (3)0.50515 (13)0.0262 (6)
H8BA0.35961.50040.51290.031*
C9B0.2666 (3)1.3773 (3)0.45474 (13)0.0253 (6)
H9BA0.27511.45330.42780.030*
C10B0.2024 (3)1.2343 (3)0.44277 (12)0.0223 (6)
C11B0.1193 (3)1.0798 (3)0.37579 (11)0.0231 (6)
H11C0.20671.04500.38060.028*
H11D0.04391.01570.39810.028*
C12B0.0627 (3)1.0796 (3)0.31969 (11)0.0203 (6)
C13B0.0402 (3)0.9793 (3)0.25173 (11)0.0199 (6)
C14B0.1555 (3)0.9272 (3)0.15448 (11)0.0190 (5)
C15B0.0435 (3)0.9761 (3)0.11971 (11)0.0205 (6)
C16B0.1880 (3)1.0798 (3)0.05979 (11)0.0190 (5)
C17B0.3088 (3)1.0223 (3)0.09096 (11)0.0177 (5)
C18B0.2900 (3)0.9505 (3)0.13989 (11)0.0179 (5)
C19B0.4140 (3)0.9067 (3)0.17522 (11)0.0194 (6)
C20B0.5258 (3)0.7806 (3)0.17060 (12)0.0248 (6)
H20B0.52170.71800.14590.030*
C21B0.6430 (3)0.7456 (3)0.20176 (13)0.0285 (7)
H21B0.71790.65820.19880.034*
C22B0.6517 (3)0.8372 (3)0.23727 (12)0.0255 (6)
H22B0.73200.81430.25870.031*
C23B0.5406 (3)0.9624 (3)0.24066 (11)0.0216 (6)
C24B0.4199 (3)0.9991 (3)0.21079 (11)0.0214 (6)
H24B0.34361.08500.21470.026*
C25B0.1006 (3)0.9448 (4)0.13195 (13)0.0278 (7)
H25D0.16020.97890.10170.042*
H25E0.15190.99310.16260.042*
H25F0.08360.84190.13950.042*
C26B0.4452 (3)1.0496 (3)0.07378 (11)0.0209 (6)
H2NA0.283 (4)0.831 (4)0.0159 (13)0.020 (8)*
H1NA0.129 (4)0.852 (4)0.0238 (14)0.026 (9)*
H2NB0.116 (4)1.215 (4)0.0027 (16)0.036 (10)*
H1NB0.274 (5)1.183 (4)0.0053 (16)0.040 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0232 (4)0.0202 (3)0.0190 (3)0.0060 (3)0.0007 (3)0.0009 (3)
O1A0.0226 (11)0.0401 (13)0.0190 (10)0.0072 (9)0.0023 (8)0.0022 (9)
O2A0.0244 (10)0.0202 (10)0.0169 (10)0.0032 (8)0.0009 (8)0.0007 (8)
O3A0.0607 (19)0.080 (2)0.0346 (15)0.0171 (16)0.0291 (14)0.0020 (14)
O4A0.0553 (17)0.0385 (14)0.0248 (12)0.0119 (12)0.0011 (11)0.0082 (10)
N1A0.0297 (14)0.0243 (13)0.0229 (13)0.0009 (11)0.0020 (11)0.0003 (10)
N2A0.0278 (14)0.0284 (14)0.0227 (13)0.0029 (11)0.0025 (11)0.0019 (11)
N3A0.0177 (11)0.0284 (13)0.0156 (11)0.0074 (10)0.0018 (9)0.0018 (10)
N4A0.0155 (12)0.0284 (13)0.0199 (12)0.0068 (11)0.0027 (10)0.0016 (10)
N5A0.0200 (13)0.0388 (15)0.0268 (14)0.0109 (11)0.0056 (10)0.0103 (11)
N6A0.0445 (17)0.0364 (16)0.0245 (14)0.0167 (14)0.0128 (13)0.0004 (12)
C1A0.0199 (14)0.0292 (16)0.0268 (15)0.0081 (12)0.0018 (12)0.0045 (12)
C2A0.0186 (14)0.0261 (15)0.0338 (17)0.0069 (12)0.0062 (12)0.0014 (13)
C3A0.0269 (15)0.0174 (13)0.0283 (16)0.0085 (12)0.0057 (12)0.0007 (11)
C4A0.0319 (16)0.0250 (15)0.0303 (17)0.0124 (13)0.0112 (13)0.0050 (12)
C5A0.048 (2)0.0266 (16)0.0243 (16)0.0156 (15)0.0109 (14)0.0040 (13)
C6A0.0421 (19)0.0228 (15)0.0234 (15)0.0116 (14)0.0031 (13)0.0011 (12)
C7A0.0294 (16)0.0194 (14)0.0269 (16)0.0070 (12)0.0010 (12)0.0021 (12)
C8A0.0260 (15)0.0142 (13)0.0239 (14)0.0078 (11)0.0027 (12)0.0013 (11)
C9A0.0213 (14)0.0180 (13)0.0248 (15)0.0045 (11)0.0037 (11)0.0006 (11)
C10A0.0260 (15)0.0244 (14)0.0207 (14)0.0088 (12)0.0034 (12)0.0020 (11)
C11A0.0233 (15)0.0260 (15)0.0213 (15)0.0039 (12)0.0009 (11)0.0004 (12)
C12A0.0185 (14)0.0236 (14)0.0211 (14)0.0035 (11)0.0010 (11)0.0028 (11)
C13A0.0175 (13)0.0229 (14)0.0165 (13)0.0049 (11)0.0027 (10)0.0024 (11)
C14A0.0181 (13)0.0233 (14)0.0182 (13)0.0063 (11)0.0007 (11)0.0032 (11)
C15A0.0183 (13)0.0281 (15)0.0158 (13)0.0064 (11)0.0006 (11)0.0009 (11)
C16A0.0180 (13)0.0254 (14)0.0130 (12)0.0056 (11)0.0019 (10)0.0025 (11)
C17A0.0153 (13)0.0271 (15)0.0151 (13)0.0054 (11)0.0018 (10)0.0033 (11)
C18A0.0176 (13)0.0210 (13)0.0147 (13)0.0028 (11)0.0001 (10)0.0051 (10)
C19A0.0182 (13)0.0212 (14)0.0202 (14)0.0069 (11)0.0023 (11)0.0009 (11)
C20A0.0233 (15)0.0243 (15)0.0272 (16)0.0036 (12)0.0009 (12)0.0021 (12)
C21A0.0183 (14)0.0247 (15)0.0390 (18)0.0007 (12)0.0009 (13)0.0015 (13)
C22A0.0235 (15)0.0277 (16)0.0376 (18)0.0058 (13)0.0127 (13)0.0064 (13)
C23A0.0317 (16)0.0261 (15)0.0206 (14)0.0120 (13)0.0065 (12)0.0008 (12)
C24A0.0205 (14)0.0206 (14)0.0208 (14)0.0070 (11)0.0019 (11)0.0009 (11)
C25A0.0219 (15)0.0364 (18)0.0287 (16)0.0115 (13)0.0066 (12)0.0064 (13)
C26A0.0206 (14)0.0263 (15)0.0147 (13)0.0039 (12)0.0049 (11)0.0025 (11)
S1B0.0244 (4)0.0207 (3)0.0181 (3)0.0055 (3)0.0014 (3)0.0021 (3)
O1B0.0316 (12)0.0241 (11)0.0218 (11)0.0076 (9)0.0063 (9)0.0027 (8)
O2B0.0193 (10)0.0233 (10)0.0165 (10)0.0022 (8)0.0020 (8)0.0013 (8)
O3B0.0428 (15)0.0419 (15)0.0556 (17)0.0091 (12)0.0321 (13)0.0043 (13)
O4B0.0333 (13)0.0393 (14)0.0402 (14)0.0031 (11)0.0077 (11)0.0170 (11)
N1B0.0301 (14)0.0273 (14)0.0220 (13)0.0054 (11)0.0050 (11)0.0027 (10)
N2B0.0308 (14)0.0245 (13)0.0201 (13)0.0062 (11)0.0053 (10)0.0003 (10)
N3B0.0139 (11)0.0262 (12)0.0172 (11)0.0054 (9)0.0023 (9)0.0011 (9)
N4B0.0155 (12)0.0376 (15)0.0205 (13)0.0103 (11)0.0027 (10)0.0072 (11)
N5B0.0196 (13)0.0344 (15)0.0262 (14)0.0087 (11)0.0045 (10)0.0051 (11)
N6B0.0297 (14)0.0279 (14)0.0242 (13)0.0101 (11)0.0101 (11)0.0018 (11)
C1B0.0180 (13)0.0185 (13)0.0245 (15)0.0046 (11)0.0003 (11)0.0027 (11)
C2B0.0177 (13)0.0220 (14)0.0264 (15)0.0077 (11)0.0012 (11)0.0071 (12)
C3B0.0231 (14)0.0227 (14)0.0234 (15)0.0058 (12)0.0017 (12)0.0050 (12)
C4B0.0273 (15)0.0292 (16)0.0221 (15)0.0112 (13)0.0034 (12)0.0005 (12)
C5B0.0313 (17)0.0372 (18)0.0213 (15)0.0121 (14)0.0022 (12)0.0097 (13)
C6B0.0275 (15)0.0256 (15)0.0289 (16)0.0095 (12)0.0036 (12)0.0127 (13)
C7B0.0173 (13)0.0221 (14)0.0288 (15)0.0061 (11)0.0019 (11)0.0075 (12)
C8B0.0234 (15)0.0197 (14)0.0354 (17)0.0063 (12)0.0015 (13)0.0059 (12)
C9B0.0232 (15)0.0204 (14)0.0311 (16)0.0069 (12)0.0016 (12)0.0016 (12)
C10B0.0199 (14)0.0253 (15)0.0212 (14)0.0074 (11)0.0043 (11)0.0027 (11)
C11B0.0239 (14)0.0249 (15)0.0202 (14)0.0077 (12)0.0000 (11)0.0004 (11)
C12B0.0169 (13)0.0254 (14)0.0185 (14)0.0064 (11)0.0008 (10)0.0012 (11)
C13B0.0188 (13)0.0257 (14)0.0150 (13)0.0086 (11)0.0003 (10)0.0029 (11)
C14B0.0193 (13)0.0188 (13)0.0170 (13)0.0032 (11)0.0003 (11)0.0010 (10)
C15B0.0201 (14)0.0216 (14)0.0201 (14)0.0070 (11)0.0003 (11)0.0022 (11)
C16B0.0162 (13)0.0237 (14)0.0179 (13)0.0065 (11)0.0015 (10)0.0029 (11)
C17B0.0132 (12)0.0199 (13)0.0188 (13)0.0033 (10)0.0008 (10)0.0016 (10)
C18B0.0191 (13)0.0155 (12)0.0177 (13)0.0026 (10)0.0024 (10)0.0019 (10)
C19B0.0175 (13)0.0220 (14)0.0191 (13)0.0084 (11)0.0005 (11)0.0028 (11)
C20B0.0231 (15)0.0236 (15)0.0262 (15)0.0051 (12)0.0033 (12)0.0000 (12)
C21B0.0208 (15)0.0264 (16)0.0339 (17)0.0004 (12)0.0049 (13)0.0000 (13)
C22B0.0181 (14)0.0305 (16)0.0250 (15)0.0050 (12)0.0065 (11)0.0077 (12)
C23B0.0235 (14)0.0252 (14)0.0164 (13)0.0077 (12)0.0044 (11)0.0008 (11)
C24B0.0193 (14)0.0215 (14)0.0204 (14)0.0021 (11)0.0045 (11)0.0024 (11)
C25B0.0237 (15)0.0347 (17)0.0258 (16)0.0122 (13)0.0032 (12)0.0052 (13)
C26B0.0191 (14)0.0230 (14)0.0186 (14)0.0036 (11)0.0053 (11)0.0030 (11)
Geometric parameters (Å, º) top
S1A—C13A1.746 (3)S1B—C13B1.742 (3)
S1A—C14A1.779 (3)S1B—C14B1.773 (3)
O1A—C10A1.378 (4)O1B—C10B1.381 (4)
O1A—C11A1.414 (4)O1B—C11B1.409 (4)
O2A—C13A1.361 (3)O2B—C12B1.370 (4)
O2A—C12A1.366 (3)O2B—C13B1.374 (3)
O3A—N6A1.216 (4)O3B—N6B1.224 (3)
O4A—N6A1.219 (4)O4B—N6B1.221 (4)
N1A—C12A1.285 (4)N1B—C12B1.273 (4)
N1A—N2A1.416 (4)N1B—N2B1.426 (4)
N2A—C13A1.287 (4)N2B—C13B1.287 (4)
N3A—C15A1.341 (4)N3B—C15B1.334 (4)
N3A—C16A1.346 (4)N3B—C16B1.359 (3)
N4A—C16A1.342 (4)N4B—C16B1.334 (4)
N4A—H2NA0.86 (4)N4B—H2NB0.92 (4)
N4A—H1NA0.84 (4)N4B—H1NB0.85 (4)
N5A—C26A1.149 (4)N5B—C26B1.149 (4)
N6A—C23A1.479 (4)N6B—C23B1.471 (4)
C1A—C2A1.361 (4)C1B—C10B1.374 (4)
C1A—C10A1.413 (4)C1B—C2B1.421 (4)
C1A—H1AA0.9500C1B—H1BA0.9500
C2A—C3A1.417 (4)C2B—C3B1.410 (4)
C2A—H2AA0.9500C2B—C7B1.424 (4)
C3A—C4A1.415 (4)C3B—C4B1.374 (4)
C3A—C8A1.422 (4)C3B—H3BA0.9500
C4A—C5A1.375 (5)C4B—C5B1.414 (5)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—C6A1.398 (5)C5B—C6B1.368 (5)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—C7A1.378 (4)C6B—C7B1.416 (4)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.416 (4)C7B—C8B1.410 (4)
C7A—H7AA0.9500C8B—C9B1.363 (5)
C8A—C9A1.419 (4)C8B—H8BA0.9500
C9A—C10A1.362 (4)C9B—C10B1.420 (4)
C9A—H9AA0.9500C9B—H9BA0.9500
C11A—C12A1.477 (4)C11B—C12B1.489 (4)
C11A—H11A0.9900C11B—H11C0.9900
C11A—H11B0.9900C11B—H11D0.9900
C14A—C18A1.397 (4)C14B—C18B1.388 (4)
C14A—C15A1.405 (4)C14B—C15B1.405 (4)
C15A—C25A1.499 (4)C15B—C25B1.503 (4)
C16A—C17A1.425 (4)C16B—C17B1.415 (4)
C17A—C18A1.395 (4)C17B—C18B1.393 (4)
C17A—C26A1.434 (4)C17B—C26B1.432 (4)
C18A—C19A1.495 (4)C18B—C19B1.501 (4)
C19A—C24A1.387 (4)C19B—C24B1.383 (4)
C19A—C20A1.395 (4)C19B—C20B1.389 (4)
C20A—C21A1.394 (4)C20B—C21B1.385 (4)
C20A—H20A0.9500C20B—H20B0.9500
C21A—C22A1.391 (5)C21B—C22B1.386 (5)
C21A—H21A0.9500C21B—H21B0.9500
C22A—C23A1.376 (5)C22B—C23B1.377 (4)
C22A—H22A0.9500C22B—H22B0.9500
C23A—C24A1.385 (4)C23B—C24B1.391 (4)
C24A—H24A0.9500C24B—H24B0.9500
C25A—H25A0.9800C25B—H25D0.9800
C25A—H25B0.9800C25B—H25E0.9800
C25A—H25C0.9800C25B—H25F0.9800
C13A—S1A—C14A99.92 (13)C13B—S1B—C14B98.96 (13)
C10A—O1A—C11A116.0 (2)C10B—O1B—C11B115.3 (2)
C13A—O2A—C12A101.6 (2)C12B—O2B—C13B101.0 (2)
C12A—N1A—N2A105.9 (2)C12B—N1B—N2B106.1 (2)
C13A—N2A—N1A105.5 (2)C13B—N2B—N1B105.2 (2)
C15A—N3A—C16A119.5 (2)C15B—N3B—C16B119.2 (2)
C16A—N4A—H2NA119 (2)C16B—N4B—H2NB125 (2)
C16A—N4A—H1NA119 (2)C16B—N4B—H1NB119 (3)
H2NA—N4A—H1NA119 (3)H2NB—N4B—H1NB115 (4)
O3A—N6A—O4A124.7 (3)O4B—N6B—O3B124.0 (3)
O3A—N6A—C23A117.7 (3)O4B—N6B—C23B118.3 (2)
O4A—N6A—C23A117.6 (3)O3B—N6B—C23B117.7 (3)
C2A—C1A—C10A119.6 (3)C10B—C1B—C2B119.6 (3)
C2A—C1A—H1AA120.2C10B—C1B—H1BA120.2
C10A—C1A—H1AA120.2C2B—C1B—H1BA120.2
C1A—C2A—C3A121.5 (3)C3B—C2B—C1B121.4 (3)
C1A—C2A—H2AA119.2C3B—C2B—C7B118.9 (3)
C3A—C2A—H2AA119.2C1B—C2B—C7B119.7 (3)
C4A—C3A—C2A122.3 (3)C4B—C3B—C2B121.3 (3)
C4A—C3A—C8A119.5 (3)C4B—C3B—H3BA119.4
C2A—C3A—C8A118.2 (3)C2B—C3B—H3BA119.4
C5A—C4A—C3A120.1 (3)C3B—C4B—C5B119.7 (3)
C5A—C4A—H4AA120.0C3B—C4B—H4BA120.1
C3A—C4A—H4AA120.0C5B—C4B—H4BA120.1
C4A—C5A—C6A120.7 (3)C6B—C5B—C4B120.2 (3)
C4A—C5A—H5AA119.7C6B—C5B—H5BA119.9
C6A—C5A—H5AA119.7C4B—C5B—H5BA119.9
C7A—C6A—C5A120.5 (3)C5B—C6B—C7B121.2 (3)
C7A—C6A—H6AA119.8C5B—C6B—H6BA119.4
C5A—C6A—H6AA119.8C7B—C6B—H6BA119.4
C6A—C7A—C8A120.5 (3)C8B—C7B—C6B123.1 (3)
C6A—C7A—H7AA119.8C8B—C7B—C2B118.3 (3)
C8A—C7A—H7AA119.8C6B—C7B—C2B118.6 (3)
C7A—C8A—C9A121.7 (3)C9B—C8B—C7B121.9 (3)
C7A—C8A—C3A118.7 (3)C9B—C8B—H8BA119.1
C9A—C8A—C3A119.6 (3)C7B—C8B—H8BA119.1
C10A—C9A—C8A119.8 (3)C8B—C9B—C10B119.5 (3)
C10A—C9A—H9AA120.1C8B—C9B—H9BA120.3
C8A—C9A—H9AA120.1C10B—C9B—H9BA120.3
C9A—C10A—O1A124.5 (3)C1B—C10B—O1B124.6 (3)
C9A—C10A—C1A121.2 (3)C1B—C10B—C9B121.0 (3)
O1A—C10A—C1A114.3 (3)O1B—C10B—C9B114.4 (3)
O1A—C11A—C12A108.0 (2)O1B—C11B—C12B108.9 (2)
O1A—C11A—H11A110.1O1B—C11B—H11C109.9
C12A—C11A—H11A110.1C12B—C11B—H11C109.9
O1A—C11A—H11B110.1O1B—C11B—H11D109.9
C12A—C11A—H11B110.1C12B—C11B—H11D109.9
H11A—C11A—H11B108.4H11C—C11B—H11D108.3
N1A—C12A—O2A113.3 (3)N1B—C12B—O2B113.9 (2)
N1A—C12A—C11A127.7 (3)N1B—C12B—C11B132.0 (3)
O2A—C12A—C11A118.9 (2)O2B—C12B—C11B114.1 (2)
N2A—C13A—O2A113.7 (3)N2B—C13B—O2B113.7 (3)
N2A—C13A—S1A129.3 (2)N2B—C13B—S1B130.8 (2)
O2A—C13A—S1A117.1 (2)O2B—C13B—S1B115.5 (2)
C18A—C14A—C15A119.7 (3)C18B—C14B—C15B119.3 (3)
C18A—C14A—S1A120.4 (2)C18B—C14B—S1B120.1 (2)
C15A—C14A—S1A119.8 (2)C15B—C14B—S1B120.6 (2)
N3A—C15A—C14A122.1 (3)N3B—C15B—C14B122.4 (3)
N3A—C15A—C25A115.9 (2)N3B—C15B—C25B116.2 (2)
C14A—C15A—C25A122.0 (3)C14B—C15B—C25B121.4 (3)
N4A—C16A—N3A116.6 (2)N4B—C16B—N3B116.8 (2)
N4A—C16A—C17A122.3 (3)N4B—C16B—C17B122.3 (3)
N3A—C16A—C17A121.1 (3)N3B—C16B—C17B120.8 (3)
C18A—C17A—C16A119.6 (3)C18B—C17B—C16B119.5 (2)
C18A—C17A—C26A121.6 (2)C18B—C17B—C26B120.8 (2)
C16A—C17A—C26A118.7 (3)C16B—C17B—C26B119.4 (2)
C17A—C18A—C14A117.8 (3)C14B—C18B—C17B118.3 (2)
C17A—C18A—C19A119.9 (2)C14B—C18B—C19B123.0 (2)
C14A—C18A—C19A122.1 (3)C17B—C18B—C19B118.7 (2)
C24A—C19A—C20A119.4 (3)C24B—C19B—C20B120.0 (3)
C24A—C19A—C18A118.8 (2)C24B—C19B—C18B118.5 (2)
C20A—C19A—C18A121.7 (3)C20B—C19B—C18B121.4 (3)
C19A—C20A—C21A120.1 (3)C21B—C20B—C19B120.5 (3)
C19A—C20A—H20A119.9C21B—C20B—H20B119.7
C21A—C20A—H20A119.9C19B—C20B—H20B119.7
C22A—C21A—C20A120.8 (3)C22B—C21B—C20B120.4 (3)
C22A—C21A—H21A119.6C22B—C21B—H21B119.8
C20A—C21A—H21A119.6C20B—C21B—H21B119.8
C23A—C22A—C21A117.7 (3)C23B—C22B—C21B118.1 (3)
C23A—C22A—H22A121.1C23B—C22B—H22B121.0
C21A—C22A—H22A121.1C21B—C22B—H22B121.0
C22A—C23A—C24A122.9 (3)C22B—C23B—C24B122.9 (3)
C22A—C23A—N6A119.6 (3)C22B—C23B—N6B119.3 (3)
C24A—C23A—N6A117.4 (3)C24B—C23B—N6B117.8 (3)
C23A—C24A—C19A119.1 (3)C19B—C24B—C23B118.1 (3)
C23A—C24A—H24A120.5C19B—C24B—H24B120.9
C19A—C24A—H24A120.5C23B—C24B—H24B120.9
C15A—C25A—H25A109.5C15B—C25B—H25D109.5
C15A—C25A—H25B109.5C15B—C25B—H25E109.5
H25A—C25A—H25B109.5H25D—C25B—H25E109.5
C15A—C25A—H25C109.5C15B—C25B—H25F109.5
H25A—C25A—H25C109.5H25D—C25B—H25F109.5
H25B—C25A—H25C109.5H25E—C25B—H25F109.5
N5A—C26A—C17A177.2 (3)N5B—C26B—C17B178.0 (3)
C12A—N1A—N2A—C13A0.5 (3)C12B—N1B—N2B—C13B0.4 (3)
C10A—C1A—C2A—C3A1.2 (5)C10B—C1B—C2B—C3B178.3 (3)
C1A—C2A—C3A—C4A176.6 (3)C10B—C1B—C2B—C7B0.8 (4)
C1A—C2A—C3A—C8A1.1 (4)C1B—C2B—C3B—C4B179.9 (3)
C2A—C3A—C4A—C5A178.8 (3)C7B—C2B—C3B—C4B0.8 (4)
C8A—C3A—C4A—C5A1.1 (4)C2B—C3B—C4B—C5B0.7 (5)
C3A—C4A—C5A—C6A1.7 (5)C3B—C4B—C5B—C6B1.1 (5)
C4A—C5A—C6A—C7A2.5 (5)C4B—C5B—C6B—C7B0.1 (5)
C5A—C6A—C7A—C8A0.5 (5)C5B—C6B—C7B—C8B178.8 (3)
C6A—C7A—C8A—C9A178.0 (3)C5B—C6B—C7B—C2B1.4 (4)
C6A—C7A—C8A—C3A2.3 (4)C3B—C2B—C7B—C8B178.4 (3)
C4A—C3A—C8A—C7A3.1 (4)C1B—C2B—C7B—C8B0.7 (4)
C2A—C3A—C8A—C7A179.1 (3)C3B—C2B—C7B—C6B1.9 (4)
C4A—C3A—C8A—C9A177.2 (3)C1B—C2B—C7B—C6B179.0 (3)
C2A—C3A—C8A—C9A0.6 (4)C6B—C7B—C8B—C9B179.1 (3)
C7A—C8A—C9A—C10A179.5 (3)C2B—C7B—C8B—C9B0.6 (4)
C3A—C8A—C9A—C10A0.1 (4)C7B—C8B—C9B—C10B0.5 (5)
C8A—C9A—C10A—O1A179.7 (3)C2B—C1B—C10B—O1B179.9 (3)
C8A—C9A—C10A—C1A0.2 (4)C2B—C1B—C10B—C9B0.7 (4)
C11A—O1A—C10A—C9A3.9 (4)C11B—O1B—C10B—C1B12.9 (4)
C11A—O1A—C10A—C1A176.0 (3)C11B—O1B—C10B—C9B167.9 (3)
C2A—C1A—C10A—C9A0.8 (5)C8B—C9B—C10B—C1B0.6 (4)
C2A—C1A—C10A—O1A179.2 (3)C8B—C9B—C10B—O1B179.8 (3)
C10A—O1A—C11A—C12A179.1 (2)C10B—O1B—C11B—C12B176.4 (2)
N2A—N1A—C12A—O2A1.3 (3)N2B—N1B—C12B—O2B0.3 (3)
N2A—N1A—C12A—C11A174.9 (3)N2B—N1B—C12B—C11B179.0 (3)
C13A—O2A—C12A—N1A1.5 (3)C13B—O2B—C12B—N1B0.2 (3)
C13A—O2A—C12A—C11A175.1 (3)C13B—O2B—C12B—C11B179.3 (2)
O1A—C11A—C12A—N1A136.7 (3)O1B—C11B—C12B—N1B8.7 (4)
O1A—C11A—C12A—O2A47.3 (4)O1B—C11B—C12B—O2B170.6 (2)
N1A—N2A—C13A—O2A0.4 (3)N1B—N2B—C13B—O2B0.3 (3)
N1A—N2A—C13A—S1A178.7 (2)N1B—N2B—C13B—S1B179.0 (2)
C12A—O2A—C13A—N2A1.1 (3)C12B—O2B—C13B—N2B0.1 (3)
C12A—O2A—C13A—S1A179.6 (2)C12B—O2B—C13B—S1B179.02 (19)
C14A—S1A—C13A—N2A36.7 (3)C14B—S1B—C13B—N2B2.7 (3)
C14A—S1A—C13A—O2A141.5 (2)C14B—S1B—C13B—O2B178.5 (2)
C13A—S1A—C14A—C18A94.8 (2)C13B—S1B—C14B—C18B98.0 (2)
C13A—S1A—C14A—C15A89.0 (2)C13B—S1B—C14B—C15B83.0 (2)
C16A—N3A—C15A—C14A3.2 (4)C16B—N3B—C15B—C14B2.7 (4)
C16A—N3A—C15A—C25A177.4 (3)C16B—N3B—C15B—C25B177.3 (3)
C18A—C14A—C15A—N3A0.6 (4)C18B—C14B—C15B—N3B4.4 (4)
S1A—C14A—C15A—N3A176.8 (2)S1B—C14B—C15B—N3B176.5 (2)
C18A—C14A—C15A—C25A180.0 (3)C18B—C14B—C15B—C25B175.7 (3)
S1A—C14A—C15A—C25A3.8 (4)S1B—C14B—C15B—C25B3.4 (4)
C15A—N3A—C16A—N4A178.0 (3)C15B—N3B—C16B—N4B177.0 (3)
C15A—N3A—C16A—C17A2.3 (4)C15B—N3B—C16B—C17B3.1 (4)
N4A—C16A—C17A—C18A178.5 (3)N4B—C16B—C17B—C18B172.8 (3)
N3A—C16A—C17A—C18A1.2 (4)N3B—C16B—C17B—C18B7.3 (4)
N4A—C16A—C17A—C26A0.6 (4)N4B—C16B—C17B—C26B1.8 (4)
N3A—C16A—C17A—C26A179.7 (3)N3B—C16B—C17B—C26B178.2 (3)
C16A—C17A—C18A—C14A3.7 (4)C15B—C14B—C18B—C17B0.1 (4)
C26A—C17A—C18A—C14A177.2 (3)S1B—C14B—C18B—C17B179.2 (2)
C16A—C17A—C18A—C19A171.9 (2)C15B—C14B—C18B—C19B177.7 (3)
C26A—C17A—C18A—C19A7.2 (4)S1B—C14B—C18B—C19B3.2 (4)
C15A—C14A—C18A—C17A2.9 (4)C16B—C17B—C18B—C14B5.5 (4)
S1A—C14A—C18A—C17A173.3 (2)C26B—C17B—C18B—C14B180.0 (3)
C15A—C14A—C18A—C19A172.7 (3)C16B—C17B—C18B—C19B172.3 (3)
S1A—C14A—C18A—C19A11.2 (4)C26B—C17B—C18B—C19B2.2 (4)
C17A—C18A—C19A—C24A111.4 (3)C14B—C18B—C19B—C24B86.1 (3)
C14A—C18A—C19A—C24A64.0 (4)C17B—C18B—C19B—C24B91.5 (3)
C17A—C18A—C19A—C20A64.7 (4)C14B—C18B—C19B—C20B97.7 (3)
C14A—C18A—C19A—C20A119.8 (3)C17B—C18B—C19B—C20B84.6 (3)
C24A—C19A—C20A—C21A0.8 (4)C24B—C19B—C20B—C21B0.6 (4)
C18A—C19A—C20A—C21A176.9 (3)C18B—C19B—C20B—C21B176.7 (3)
C19A—C20A—C21A—C22A0.9 (5)C19B—C20B—C21B—C22B1.2 (5)
C20A—C21A—C22A—C23A0.8 (5)C20B—C21B—C22B—C23B0.4 (5)
C21A—C22A—C23A—C24A0.5 (5)C21B—C22B—C23B—C24B1.2 (5)
C21A—C22A—C23A—N6A177.4 (3)C21B—C22B—C23B—N6B177.0 (3)
O3A—N6A—C23A—C22A1.7 (5)O4B—N6B—C23B—C22B173.0 (3)
O4A—N6A—C23A—C22A177.7 (3)O3B—N6B—C23B—C22B8.5 (4)
O3A—N6A—C23A—C24A178.8 (3)O4B—N6B—C23B—C24B8.7 (4)
O4A—N6A—C23A—C24A0.6 (4)O3B—N6B—C23B—C24B169.7 (3)
C22A—C23A—C24A—C19A0.4 (5)C20B—C19B—C24B—C23B0.8 (4)
N6A—C23A—C24A—C19A177.3 (3)C18B—C19B—C24B—C23B175.3 (3)
C20A—C19A—C24A—C23A0.5 (4)C22B—C23B—C24B—C19B1.8 (4)
C18A—C19A—C24A—C23A176.7 (3)N6B—C23B—C24B—C19B176.4 (3)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1B/C2B/C7B–C10B, C2B–C7B, C1A/C2A/C3A/C8A–C10A and O2A/C12A/N1A/N2A/C13A rings, respecively.
D—H···AD—HH···AD···AD—H···A
N4A—H2NA···N5Bi0.86 (4)2.21 (4)3.025 (4)158 (3)
N4A—H1NA···N3Bii0.84 (4)2.23 (4)3.056 (4)165 (4)
N4B—H2NB···N3Aii0.92 (4)2.08 (4)2.991 (4)174 (4)
N4B—H1NB···N5Ai0.85 (5)2.34 (5)3.157 (4)162 (4)
C11A—H11B···O1Biii0.992.363.332 (4)168
C11B—H11C···O3Biv0.992.603.173 (4)117
C21B—H21B···N2Av0.952.543.333 (4)142
C22A—H22A···N1Bvi0.952.603.540 (4)169
C2A—H2AA···Cg1vi0.952.783.492 (3)133
C4A—H4AA···Cg2vi0.952.623.457 (4)147
C7A—H7AA···Cg1iii0.952.803.557 (3)138
C3B—H3BA···Cg3vii0.952.673.440 (3)138
C8B—H8BA···Cg3viii0.952.833.599 (3)139
C24A—H24A···Cg40.952.923.652 (3)135
Symmetry codes: (i) x+1, y+2, z; (ii) x, y+2, z; (iii) x, y1, z; (iv) x1, y, z; (v) x+1, y, z; (vi) x+1, y1, z; (vii) x, y+1, z+1; (viii) x, y+2, z+1.

Experimental details

Crystal data
Chemical formulaC26H18N6O4S
Mr510.52
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)9.6132 (9), 9.8928 (10), 25.724 (2)
α, β, γ (°)83.215 (2), 84.102 (2), 72.564 (2)
V3)2311.8 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.23 × 0.19 × 0.09
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.958, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
9469, 9469, 8293
Rint0.000
(sin θ/λ)max1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.164, 1.20
No. of reflections9469
No. of parameters686
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.36

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2, Cg3 and Cg4 are the centroids of the C1B/C2B/C7B–C10B, C2B–C7B, C1A/C2A/C3A/C8A–C10A and O2A/C12A/N1A/N2A/C13A rings, respecively.
D—H···AD—HH···AD···AD—H···A
N4A—H2NA···N5Bi0.86 (4)2.21 (4)3.025 (4)158 (3)
N4A—H1NA···N3Bii0.84 (4)2.23 (4)3.056 (4)165 (4)
N4B—H2NB···N3Aii0.92 (4)2.08 (4)2.991 (4)174 (4)
N4B—H1NB···N5Ai0.85 (5)2.34 (5)3.157 (4)162 (4)
C11A—H11B···O1Biii0.992.363.332 (4)168
C11B—H11C···O3Biv0.992.603.173 (4)117
C21B—H21B···N2Av0.952.543.333 (4)142
C22A—H22A···N1Bvi0.952.603.540 (4)169
C2A—H2AA···Cg1vi0.952.783.492 (3)133
C4A—H4AA···Cg2vi0.952.623.457 (4)147
C7A—H7AA···Cg1iii0.952.803.557 (3)138
C3B—H3BA···Cg3vii0.952.673.440 (3)138
C8B—H8BA···Cg3viii0.952.833.599 (3)139
C24A—H24A···Cg40.952.923.652 (3)135
Symmetry codes: (i) x+1, y+2, z; (ii) x, y+2, z; (iii) x, y1, z; (iv) x1, y, z; (v) x+1, y, z; (vi) x+1, y1, z; (vii) x, y+1, z+1; (viii) x, y+2, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-3194-2011.

Acknowledgements

The authors thank Universiti Sains Malaysia (USM) for the RUC grant (Structure Determination of 50 kDa Outer Membrane Proteins From S.typhi By X-ray Protein Crystallography, No. 1001/PSKBP/8630013) and APEX DE2012 grant (No. 1002/PFIZIK/910323). CSC thanks Universiti Sains Malaysia for a postdoctoral research fellowship. PP thanks the UGC, New Delhi, for the award of a junior research fellowship.

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Volume 69| Part 4| April 2013| Pages o491-o492
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