organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 5| May 2010| Pages o1200-o1201

2-[(1Z)-(9-Ethyl-9H-carbazol-3-yl)methyl­ene­amino]-4,5,6,7-tetra­hydro-1-benzo­thio­phene-3-carbo­nitrile–benzene (2/1)

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Chemistry, Faculty of Science, King Abdulaziz University, Jeddah, Saudi Arabia
*Correspondence e-mail: hkfun@usm.my

(Received 22 March 2010; accepted 23 April 2010; online 28 April 2010)

In the title compound, 2C24H21N3S·C6H6, the two independent Schiff base mol­ecules (A and B) in the asymmetric unit differ in the orientation of the tetra­hydro­benzothio­phene ring system with respect to the carbazole ring system by 180° rotation about the C—C bond in the C—C=N—C linkage. The two mol­ecules also differ in the orientation of the ethyl groups [C—N—C—C torsion angle of 90.7 (3)° in mol­ecule A, and −79.4 (3)° in mol­ecule B]. In mol­ecule B, two methyl­ene C atoms of the cyclo­hexene ring are disordered over two sites with occupancies of 0.58 (1) and 0.42 (1). The cyclo­hexene rings in both mol­ecules adopt half-chair conformations. The dihedral angle between the thio­phene ring and the carbazole ring system is 8.07 (9)° in mol­ecule A [3.10 (9)° in mol­ecule B]. In the crystal structure, the independent mol­ecules are linked into dimers by inter­molecular C—H⋯N hydrogen bonds. In addition, C—H⋯π inter­actions are observed.

Related literature

For biological and other applications of Schiff base compounds, see: Abu-Hussen (2006[Abu-Hussen, A. A. A. (2006). J. Coord. Chem. 59, 157-176.]); Elerman et al. (2002[Elerman, Y., Kabak, M. & Elmali, A. (2002). Z. Naturforsch. Teil B, 57, 651-656.]); Panneerselvam et al. (2005[Panneerselvam, P., Nair, R. P., Vijayalakshmi, G., Subramanian, E. H. & Sridhar, S. K. (2005). Eur. J. Med. Chem. 40, 225-229.]); Walsh et al. (1996[Walsh, O. M., Meegan, M. J., Prendergast, R. M. & Nakib, T. A. (1996). Eur. J. Med. Chem. 31, 989-1000.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For a related structure, see: Elerman & Elmali (1998[Elerman, Y. & Elmali, A. (1998). Acta Cryst. C54, 529-531.]).

[Scheme 1]

Experimental

Crystal data
  • 2C24H21N3S·C6H6

  • Mr = 845.10

  • Triclinic, [P \overline 1]

  • a = 11.4816 (1) Å

  • b = 13.7322 (2) Å

  • c = 14.8358 (2) Å

  • α = 81.841 (1)°

  • β = 77.083 (1)°

  • γ = 83.864 (1)°

  • V = 2250.00 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.16 mm−1

  • T = 293 K

  • 0.45 × 0.15 × 0.07 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.989

  • 48693 measured reflections

  • 13169 independent reflections

  • 6227 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.070

  • wR(F2) = 0.167

  • S = 1.01

  • 13169 reflections

  • 580 parameters

  • 63 restraints

  • H-atom parameters constrained

  • Δρmax = 0.31 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1B–C6B, C7A–C12A and C14A–C16A/C21A/S1A rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C22A—H22A⋯N3Bi 0.97 2.59 3.487 (3) 155
C11A—H11ACg1ii 0.93 2.65 3.499 (3) 153
C11B—H11BCg2i 0.93 2.82 3.725 (3) 166
C27—H27ACg3iii 0.93 2.71 3.625 (6) 169
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y, z; (iii) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. 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

Schiff bases are an important class of compounds in medicinal and pharmaceutical field. They show biological applications including anti-bacterial (Abu-Hussen, 2006), anti-fungal (Panneerselvam et al., 2005) and anti-tumor (Walsh et al., 1996) activities. In the field of coordination chemistry, they are used extensively as ligands due to intramolecular hydrogen bonds between O and N atoms, which is applicable for the formation of metal complexes. Schiff bases are also used in the field of photochromism and thermochromism in the solid state (Elerman et al., 2002). In this paper, we report the crystal structure of the title Schiff base compound.

The asymmetric unit of the title compound (Fig. 1) consists of two crystallographically independent Schiff base molecules and a benzene solvent molecule. The two independent main molecules differ in the orientation of the tetrahydrobenzothiophene ring system with respect to the 9H-carbazole ring system by 180° rotation about the C9—C13 bond. The conformation of the ethyl group (C22/C23) also differs in both molecules, with C1A—N1A—C22A—C23A torsion angle of 90.7 (3)° in molecule A, indicating (+)-anti-clinal conformation, whereas C1B—N1B—C22B—C23B torsion angle of -79.4 (3)° in molecule B, indicating (-)-syn-clinal conformation.

In molecule A, the cyclohexene ring (C16A-C21A) adopts a half-chair conformation, with puckering parameters of Q = 0.433 (3) Å, θ = 49.1 (4)° and ϕ = 145.4 (5)° (Cremer & Pople, 1975). In both the major and minor conformers of molecule B, the cyclohexene rings adopt half-chair conformations; the puckering parameters: Q = 0.508 (7) Å, θ = 50.0 (6)° and ϕ = 155.0 (7)° for the major conformer and Q = 0.467 (9) Å, θ = 130.4 (7)°, and ϕ = 330.0 (10)° for the minor conformer. The dihedral angle between the thiophene ring and the carbazole ring system is 8.07 (9)° in molecule A and 3.10 (9)° in molecule B. The bond lengths and angles are comparable to a related 4,5,6,7-tetrahydro-1-benzothiophene-3-carbonitrile structure (Elerman & Elmali, 1998).

In the crystal structure (Fig. 2), the benzene solvent molecule is not involved in intermolecular hydrogen bonding. The Schiff base molecules are linked into dimers by pairs of intermolecular C22A—H22A···N3B hydrogen bonds (Table 1). The crystal structure is further stabilized by weak intermolecular C—H···π interactions (Table 1).

Related literature top

For biological and other applications of Schiff base compounds, see: Abu-Hussen (2006); Elerman et al. (2002); Panneerselvam et al. (2005); Walsh et al. (1996). For ring puckering parameters, see: Cremer & Pople (1975). For a related structure, see: Elerman & Elmali (1998).

Experimental top

A mixture of carbazolealdehyde (0.50 g, 0.0022 mol) and 2-amino-3-cyanobenzothiophene (0.38 g, 0.0022 mol) in methanol (15 ml) was refluxed for 5 h with stirring to give a light yellow precipitate. It was then filtered and washed with methanol to give the pure Schiff base. Good quality single crystals were recrystallized from a mixture of benzene, chloroform and methanol (4:4:2). (Yield 78 %, M.p. 468 K).

Refinement top

Atoms C18B and C19B are both disordered over two positions with occupancies of 0.58 (1) and 0.42 (1). In both disorder components, the C—C distances involving the disordered atoms were restrained to be equal. In the benzene solvent molecule, the C—C distances were restrained to 1.384 (3) Å. The Uij components of atom C18X and all C atoms of the benzene solvent molecule were restrained to an approximate isotropic behaviour. H atoms were placed in their calculated positions [C–H = 0.93–97 Å] and refined using a riding model with Uiso = 1.2 or 1.5 Ueq(C).

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. Displacement ellipsoids are drawn at the 20 % probability level. For clarity, the benzene solvent molecule is not shown.
[Figure 2] Fig. 2. The crystal structure of the title compound, viewed along the a axis, showing the molecules being linked into dimers. Only the major disordered components are shown. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.
2-[(1Z)-(9-Ethyl-9H-carbazol-3-yl)methyleneamino]-4,5,6,7- tetrahydro-1-benzothiophene-3-carbonitrile–benzene (2/1) top
Crystal data top
2C24H21N3S·C6H6Z = 2
Mr = 845.10F(000) = 892
Triclinic, P1Dx = 1.247 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.4816 (1) ÅCell parameters from 6974 reflections
b = 13.7322 (2) Åθ = 2.4–21.2°
c = 14.8358 (2) ŵ = 0.16 mm1
α = 81.841 (1)°T = 293 K
β = 77.083 (1)°Plate, yellow
γ = 83.864 (1)°0.45 × 0.15 × 0.07 mm
V = 2250.00 (5) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
13169 independent reflections
Radiation source: fine-focus sealed tube6227 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ and ω scansθmax = 30.1°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 1616
Tmin = 0.931, Tmax = 0.989k = 1919
48693 measured reflectionsl = 2020
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)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0574P)2 + 0.4624P]
where P = (Fo2 + 2Fc2)/3
13169 reflections(Δ/σ)max = 0.001
580 parametersΔρmax = 0.31 e Å3
63 restraintsΔρmin = 0.20 e Å3
Crystal data top
2C24H21N3S·C6H6γ = 83.864 (1)°
Mr = 845.10V = 2250.00 (5) Å3
Triclinic, P1Z = 2
a = 11.4816 (1) ÅMo Kα radiation
b = 13.7322 (2) ŵ = 0.16 mm1
c = 14.8358 (2) ÅT = 293 K
α = 81.841 (1)°0.45 × 0.15 × 0.07 mm
β = 77.083 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
13169 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
6227 reflections with I > 2σ(I)
Tmin = 0.931, Tmax = 0.989Rint = 0.048
48693 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07063 restraints
wR(F2) = 0.167H-atom parameters constrained
S = 1.01Δρmax = 0.31 e Å3
13169 reflectionsΔρmin = 0.20 e Å3
580 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.28193 (6)0.58795 (5)0.14257 (5)0.0645 (2)
N1A0.35074 (17)0.81675 (13)0.21845 (13)0.0532 (5)
N2A0.03256 (16)0.58008 (14)0.08737 (14)0.0554 (5)
N3A0.0583 (2)0.3886 (2)0.2688 (2)0.0964 (8)
C1A0.4457 (2)0.75882 (16)0.18956 (15)0.0496 (5)
C2A0.5683 (2)0.76344 (19)0.22354 (18)0.0622 (7)
H2A0.59830.81200.27090.075*
C3A0.6437 (2)0.6938 (2)0.1847 (2)0.0693 (7)
H3A0.72590.69420.20750.083*
C4A0.6002 (2)0.6226 (2)0.1121 (2)0.0718 (7)
H4A0.65370.57730.08640.086*
C5A0.4785 (2)0.61827 (18)0.07770 (18)0.0630 (7)
H5A0.44970.57090.02870.076*
C6A0.39982 (19)0.68584 (16)0.11748 (15)0.0481 (5)
C7A0.27086 (19)0.69989 (15)0.10253 (14)0.0452 (5)
C8A0.17748 (19)0.65416 (16)0.04151 (15)0.0492 (5)
H8A0.19320.60220.00270.059*
C9A0.0596 (2)0.68660 (16)0.04674 (15)0.0504 (5)
C10A0.0376 (2)0.76495 (18)0.11427 (17)0.0603 (6)
H10A0.04130.78490.11820.072*
C11A0.1282 (2)0.81317 (17)0.17470 (16)0.0573 (6)
H11A0.11190.86540.21850.069*
C12A0.2451 (2)0.78087 (16)0.16790 (15)0.0478 (5)
C13A0.0413 (2)0.64287 (17)0.01630 (17)0.0559 (6)
H13A0.11730.66150.00450.067*
C14A0.13382 (19)0.54642 (16)0.14786 (16)0.0514 (6)
C15A0.13252 (19)0.47652 (16)0.22303 (16)0.0488 (5)
C16A0.2488 (2)0.45626 (16)0.27752 (15)0.0486 (5)
C17A0.2730 (2)0.3862 (2)0.36522 (18)0.0672 (7)
H17A0.21540.39240.40250.081*
H17B0.26330.31910.34980.081*
C18A0.3980 (3)0.4065 (2)0.4210 (2)0.0870 (9)
H18A0.41790.35060.46790.104*
H18B0.39970.46370.45290.104*
C19A0.4892 (3)0.4243 (3)0.3640 (2)0.0874 (9)
H19A0.56690.43670.40440.105*
H19B0.49170.36500.33610.105*
C20A0.4682 (2)0.5109 (2)0.28643 (19)0.0695 (7)
H20A0.51320.50490.23960.083*
H20B0.49610.57250.31200.083*
C21A0.3371 (2)0.51130 (17)0.24260 (16)0.0534 (6)
C22A0.3612 (2)0.90256 (18)0.28954 (17)0.0651 (7)
H22A0.43260.93430.28930.078*
H22B0.29260.94940.27370.078*
C23A0.3678 (3)0.8773 (2)0.38548 (18)0.0853 (9)
H23A0.37590.93620.42910.128*
H23B0.29590.84830.38700.128*
H23C0.43570.83130.40190.128*
C24A0.0248 (2)0.42838 (19)0.24646 (18)0.0624 (7)
S1B0.38291 (6)0.72056 (5)0.14806 (5)0.0707 (2)
N1B0.91999 (18)1.09596 (14)0.17385 (13)0.0557 (5)
N2B0.50847 (18)0.88652 (15)0.13816 (13)0.0599 (5)
N3B0.3760 (2)0.9764 (2)0.36567 (18)0.0917 (8)
C1B0.9522 (2)1.04208 (17)0.24963 (16)0.0530 (6)
C2B1.0415 (2)1.05656 (19)0.32907 (17)0.0618 (7)
H2B1.08981.10890.33870.074*
C3B1.0561 (2)0.9905 (2)0.39332 (18)0.0706 (7)
H3B1.11560.99840.44720.085*
C4B0.9841 (2)0.9125 (2)0.37945 (17)0.0703 (7)
H4B0.99610.86920.42410.084*
C5B0.8949 (2)0.8980 (2)0.30040 (16)0.0605 (6)
H5B0.84670.84570.29170.073*
C6B0.87815 (19)0.96298 (17)0.23398 (15)0.0493 (5)
C7B0.79972 (19)0.96862 (16)0.14364 (15)0.0482 (5)
C8B0.7109 (2)0.91230 (17)0.08940 (15)0.0529 (6)
H8B0.68980.85820.11180.063*
C9B0.6528 (2)0.93600 (17)0.00138 (16)0.0535 (6)
C10B0.6838 (2)1.01967 (18)0.03051 (16)0.0593 (6)
H10B0.64391.03620.08880.071*
C11B0.7708 (2)1.07744 (18)0.02177 (17)0.0594 (6)
H11B0.79021.13240.00030.071*
C12B0.8295 (2)1.05139 (17)0.10915 (16)0.0517 (6)
C13B0.5630 (2)0.87384 (19)0.05443 (17)0.0596 (6)
H13B0.54350.82170.02840.071*
C14B0.4238 (2)0.82359 (18)0.18658 (16)0.0574 (6)
C15B0.3571 (2)0.83434 (19)0.27491 (16)0.0574 (6)
C16B0.2759 (2)0.7603 (2)0.31164 (17)0.0590 (6)
C17B0.1949 (2)0.7533 (2)0.40691 (18)0.0787 (8)
H17C0.24350.73240.45290.094*0.580 (10)
H17D0.15770.81860.41780.094*0.580 (10)
H17E0.12620.80000.40880.094*0.420 (10)
H17F0.23720.76400.45320.094*0.420 (10)
C18B0.1000 (5)0.6851 (5)0.4213 (6)0.094 (3)0.580 (10)
H18C0.03600.71430.39070.113*0.580 (10)
H18D0.06670.66900.48720.113*0.580 (10)
C19B0.1608 (7)0.5936 (5)0.3786 (4)0.097 (3)0.580 (10)
H19C0.10460.54280.39460.117*0.580 (10)
H19D0.22810.56990.40740.117*0.580 (10)
C18X0.1499 (9)0.6467 (6)0.4240 (7)0.082 (3)0.420 (10)
H18E0.21610.60120.43760.098*0.420 (10)
H18F0.08760.64370.48030.098*0.420 (10)
C19X0.1007 (7)0.6051 (8)0.3504 (5)0.085 (3)0.420 (10)
H19E0.07670.53870.37190.102*0.420 (10)
H19F0.03320.64680.33380.102*0.420 (10)
C20B0.2076 (3)0.6061 (2)0.2700 (2)0.0834 (9)
H20C0.25680.54790.25000.100*0.580 (10)
H20D0.14140.61790.23810.100*0.580 (10)
H20E0.26000.54830.28100.100*0.420 (10)
H20F0.18220.60140.21350.100*0.420 (10)
C21B0.2802 (2)0.6939 (2)0.25154 (19)0.0662 (7)
C22B0.9866 (2)1.17511 (18)0.1602 (2)0.0675 (7)
H22C0.93461.21660.11760.081*
H22D1.01111.21560.21930.081*
C23B1.0961 (3)1.1365 (2)0.1218 (2)0.0892 (9)
H23D1.13881.19090.11600.134*
H23E1.14731.09460.16330.134*
H23F1.07201.09950.06170.134*
C24B0.3697 (2)0.9139 (2)0.32369 (18)0.0665 (7)
C250.3449 (4)0.1706 (3)0.5697 (4)0.1256 (15)
H25A0.39550.11380.57700.151*
C260.3230 (4)0.2345 (4)0.6346 (3)0.1390 (16)
H26A0.35580.22150.68740.167*
C270.2512 (5)0.3183 (4)0.6194 (4)0.1336 (17)
H27A0.23390.36220.66380.160*
C280.2037 (4)0.3403 (3)0.5419 (4)0.1294 (17)
H28A0.15790.39940.53240.155*
C290.2247 (4)0.2739 (4)0.4784 (3)0.1280 (15)
H29A0.19230.28660.42550.154*
C300.2938 (4)0.1888 (4)0.4942 (3)0.1156 (14)
H30A0.30620.14230.45250.139*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0501 (4)0.0724 (4)0.0636 (4)0.0010 (3)0.0070 (3)0.0043 (3)
N1A0.0549 (12)0.0531 (11)0.0460 (11)0.0064 (9)0.0053 (9)0.0061 (9)
N2A0.0508 (11)0.0565 (12)0.0528 (12)0.0063 (9)0.0015 (9)0.0040 (10)
N3A0.0632 (16)0.099 (2)0.122 (2)0.0068 (14)0.0265 (16)0.0024 (17)
C1A0.0507 (13)0.0514 (13)0.0442 (13)0.0043 (10)0.0036 (11)0.0068 (10)
C2A0.0581 (15)0.0664 (16)0.0602 (16)0.0146 (13)0.0042 (13)0.0071 (13)
C3A0.0501 (14)0.0766 (18)0.0796 (19)0.0084 (13)0.0039 (14)0.0170 (16)
C4A0.0542 (16)0.0708 (18)0.087 (2)0.0061 (13)0.0172 (15)0.0039 (16)
C5A0.0568 (15)0.0598 (15)0.0654 (17)0.0018 (12)0.0084 (13)0.0039 (13)
C6A0.0492 (13)0.0477 (12)0.0443 (13)0.0010 (10)0.0049 (10)0.0069 (10)
C7A0.0499 (12)0.0441 (12)0.0388 (12)0.0029 (9)0.0065 (10)0.0051 (10)
C8A0.0545 (14)0.0456 (12)0.0413 (12)0.0009 (10)0.0029 (11)0.0001 (10)
C9A0.0498 (13)0.0515 (13)0.0450 (13)0.0009 (10)0.0031 (11)0.0046 (11)
C10A0.0498 (14)0.0666 (16)0.0590 (15)0.0027 (12)0.0087 (12)0.0003 (13)
C11A0.0585 (15)0.0568 (14)0.0507 (14)0.0035 (12)0.0111 (12)0.0068 (11)
C12A0.0520 (13)0.0479 (12)0.0393 (12)0.0008 (10)0.0035 (10)0.0026 (10)
C13A0.0476 (13)0.0606 (15)0.0560 (15)0.0020 (11)0.0038 (12)0.0082 (12)
C14A0.0460 (12)0.0533 (13)0.0516 (14)0.0049 (10)0.0014 (11)0.0090 (11)
C15A0.0439 (12)0.0499 (13)0.0516 (14)0.0021 (10)0.0063 (11)0.0094 (11)
C16A0.0480 (13)0.0509 (13)0.0454 (13)0.0054 (10)0.0038 (11)0.0092 (10)
C17A0.0643 (16)0.0699 (17)0.0602 (16)0.0107 (13)0.0016 (13)0.0018 (13)
C18A0.0717 (19)0.101 (2)0.073 (2)0.0109 (16)0.0082 (17)0.0050 (17)
C19A0.0588 (17)0.122 (3)0.075 (2)0.0309 (17)0.0083 (16)0.0096 (19)
C20A0.0441 (13)0.0883 (19)0.0717 (18)0.0063 (13)0.0000 (13)0.0132 (15)
C21A0.0463 (13)0.0589 (14)0.0524 (14)0.0078 (11)0.0023 (11)0.0086 (11)
C22A0.0695 (17)0.0569 (15)0.0603 (16)0.0095 (12)0.0058 (13)0.0121 (12)
C23A0.111 (2)0.0760 (19)0.0556 (17)0.0056 (17)0.0047 (16)0.0147 (14)
C24A0.0514 (15)0.0620 (16)0.0688 (17)0.0038 (12)0.0055 (13)0.0031 (13)
S1B0.0759 (5)0.0701 (4)0.0595 (4)0.0001 (3)0.0028 (4)0.0085 (3)
N1B0.0635 (12)0.0509 (11)0.0520 (12)0.0042 (9)0.0134 (10)0.0024 (9)
N2B0.0579 (12)0.0684 (13)0.0458 (12)0.0043 (10)0.0037 (10)0.0002 (10)
N3B0.0908 (19)0.112 (2)0.0738 (17)0.0163 (16)0.0070 (14)0.0249 (16)
C1B0.0545 (14)0.0568 (14)0.0454 (13)0.0036 (11)0.0163 (11)0.0045 (11)
C2B0.0590 (15)0.0697 (16)0.0511 (15)0.0039 (12)0.0111 (12)0.0101 (13)
C3B0.0669 (17)0.094 (2)0.0426 (14)0.0024 (15)0.0040 (13)0.0057 (14)
C4B0.0740 (18)0.092 (2)0.0437 (14)0.0003 (16)0.0083 (13)0.0153 (14)
C5B0.0610 (15)0.0772 (17)0.0442 (14)0.0056 (13)0.0104 (12)0.0112 (12)
C6B0.0484 (13)0.0581 (14)0.0404 (12)0.0040 (11)0.0133 (10)0.0025 (11)
C7B0.0492 (13)0.0524 (13)0.0423 (12)0.0044 (10)0.0125 (11)0.0048 (10)
C8B0.0549 (14)0.0572 (14)0.0464 (13)0.0001 (11)0.0112 (11)0.0079 (11)
C9B0.0531 (14)0.0599 (14)0.0447 (13)0.0050 (11)0.0098 (11)0.0045 (11)
C10B0.0674 (16)0.0650 (16)0.0416 (13)0.0082 (13)0.0078 (12)0.0099 (12)
C11B0.0715 (17)0.0567 (15)0.0525 (15)0.0037 (12)0.0169 (13)0.0154 (12)
C12B0.0573 (14)0.0513 (13)0.0450 (13)0.0049 (11)0.0164 (11)0.0014 (11)
C13B0.0575 (15)0.0661 (16)0.0517 (15)0.0030 (12)0.0097 (12)0.0045 (12)
C14B0.0547 (14)0.0641 (15)0.0488 (14)0.0056 (12)0.0101 (12)0.0002 (12)
C15B0.0531 (14)0.0705 (16)0.0451 (14)0.0077 (12)0.0115 (12)0.0023 (12)
C16B0.0460 (13)0.0734 (17)0.0496 (14)0.0070 (12)0.0062 (11)0.0039 (13)
C17B0.0623 (17)0.102 (2)0.0585 (17)0.0043 (16)0.0010 (14)0.0067 (16)
C18B0.040 (3)0.157 (7)0.080 (4)0.020 (4)0.004 (3)0.003 (4)
C19B0.061 (4)0.065 (4)0.149 (8)0.018 (4)0.002 (5)0.016 (4)
C18X0.038 (5)0.145 (8)0.059 (5)0.020 (5)0.002 (4)0.004 (5)
C19X0.051 (5)0.101 (6)0.097 (7)0.013 (5)0.005 (5)0.016 (5)
C20B0.078 (2)0.076 (2)0.089 (2)0.0112 (15)0.0121 (17)0.0067 (17)
C21B0.0565 (15)0.0678 (17)0.0664 (17)0.0037 (13)0.0087 (13)0.0050 (14)
C22B0.0768 (18)0.0512 (15)0.0759 (18)0.0068 (13)0.0204 (15)0.0041 (13)
C23B0.081 (2)0.086 (2)0.111 (3)0.0008 (16)0.0391 (19)0.0243 (19)
C24B0.0595 (16)0.087 (2)0.0484 (15)0.0008 (14)0.0069 (13)0.0038 (15)
C250.096 (3)0.097 (3)0.156 (4)0.003 (2)0.014 (3)0.009 (3)
C260.114 (3)0.178 (5)0.132 (4)0.042 (3)0.026 (3)0.022 (4)
C270.128 (4)0.118 (4)0.162 (4)0.040 (3)0.005 (3)0.079 (3)
C280.080 (3)0.086 (3)0.196 (5)0.003 (2)0.011 (3)0.008 (3)
C290.093 (3)0.183 (5)0.098 (3)0.044 (3)0.005 (2)0.017 (3)
C300.119 (3)0.121 (3)0.098 (3)0.038 (3)0.032 (2)0.051 (3)
Geometric parameters (Å, º) top
S1A—C21A1.729 (2)C3B—C4B1.388 (4)
S1A—C14A1.750 (2)C3B—H3B0.93
N1A—C12A1.376 (3)C4B—C5B1.380 (3)
N1A—C1A1.390 (3)C4B—H4B0.93
N1A—C22A1.462 (3)C5B—C6B1.390 (3)
N2A—C13A1.279 (3)C5B—H5B0.93
N2A—C14A1.379 (3)C6B—C7B1.445 (3)
N3A—C24A1.139 (3)C7B—C8B1.382 (3)
C1A—C2A1.390 (3)C7B—C12B1.413 (3)
C1A—C6A1.408 (3)C8B—C9B1.393 (3)
C2A—C3A1.373 (4)C8B—H8B0.93
C2A—H2A0.93C9B—C10B1.409 (3)
C3A—C4A1.388 (4)C9B—C13B1.443 (3)
C3A—H3A0.93C10B—C11B1.370 (3)
C4A—C5A1.381 (3)C10B—H10B0.93
C4A—H4A0.93C11B—C12B1.398 (3)
C5A—C6A1.389 (3)C11B—H11B0.93
C5A—H5A0.93C13B—H13B0.93
C6A—C7A1.443 (3)C14B—C15B1.381 (3)
C7A—C8A1.383 (3)C15B—C16B1.421 (3)
C7A—C12A1.420 (3)C15B—C24B1.430 (4)
C8A—C9A1.394 (3)C16B—C21B1.353 (4)
C8A—H8A0.93C16B—C17B1.505 (3)
C9A—C10A1.405 (3)C17B—C18B1.472 (5)
C9A—C13A1.444 (3)C17B—C18X1.573 (7)
C10A—C11A1.374 (3)C17B—H17C0.97
C10A—H10A0.93C17B—H17D0.97
C11A—C12A1.388 (3)C17B—H17E0.96
C11A—H11A0.93C17B—H17F0.96
C13A—H13A0.93C18B—C19B1.520 (6)
C14A—C15A1.366 (3)C18B—H18C0.97
C15A—C24A1.428 (4)C18B—H18D0.97
C15A—C16A1.430 (3)C19B—C20B1.571 (6)
C16A—C21A1.352 (3)C19B—H19C0.97
C16A—C17A1.495 (3)C19B—H19D0.97
C17A—C18A1.506 (4)C18X—C19X1.535 (7)
C17A—H17A0.97C18X—H18E0.97
C17A—H17B0.97C18X—H18F0.97
C18A—C19A1.467 (4)C19X—C20B1.508 (6)
C18A—H18A0.97C19X—H19E0.97
C18A—H18B0.97C19X—H19F0.97
C19A—C20A1.531 (4)C20B—C21B1.497 (4)
C19A—H19A0.97C20B—H20C0.97
C19A—H19B0.97C20B—H20D0.97
C20A—C21A1.501 (3)C20B—H20E0.96
C20A—H20A0.97C20B—H20F0.96
C20A—H20B0.97C22B—C23B1.510 (4)
C22A—C23A1.496 (4)C22B—H22C0.97
C22A—H22A0.97C22B—H22D0.97
C22A—H22B0.97C23B—H23D0.96
C23A—H23A0.96C23B—H23E0.96
C23A—H23B0.96C23B—H23F0.96
C23A—H23C0.96C25—C261.358 (7)
S1B—C21B1.734 (3)C25—C301.358 (7)
S1B—C14B1.743 (3)C25—H25A0.93
N1B—C12B1.378 (3)C26—C271.364 (8)
N1B—C1B1.393 (3)C26—H26A0.93
N1B—C22B1.455 (3)C27—C281.363 (8)
N2B—C13B1.287 (3)C27—H27A0.93
N2B—C14B1.378 (3)C28—C291.368 (7)
N3B—C24B1.146 (3)C28—H28A0.93
C1B—C2B1.385 (3)C29—C301.363 (7)
C1B—C6B1.412 (3)C29—H29A0.93
C2B—C3B1.379 (4)C30—H30A0.93
C2B—H2B0.93
C21A—S1A—C14A91.75 (11)C7B—C8B—H8B119.8
C12A—N1A—C1A108.65 (18)C9B—C8B—H8B119.8
C12A—N1A—C22A125.6 (2)C8B—C9B—C10B119.1 (2)
C1A—N1A—C22A125.74 (19)C8B—C9B—C13B118.9 (2)
C13A—N2A—C14A120.6 (2)C10B—C9B—C13B122.1 (2)
N1A—C1A—C2A129.5 (2)C11B—C10B—C9B122.0 (2)
N1A—C1A—C6A109.02 (19)C11B—C10B—H10B119.0
C2A—C1A—C6A121.5 (2)C9B—C10B—H10B119.0
C3A—C2A—C1A117.6 (2)C10B—C11B—C12B118.1 (2)
C3A—C2A—H2A121.2C10B—C11B—H11B121.0
C1A—C2A—H2A121.2C12B—C11B—H11B121.0
C2A—C3A—C4A121.7 (2)N1B—C12B—C11B129.4 (2)
C2A—C3A—H3A119.1N1B—C12B—C7B109.3 (2)
C4A—C3A—H3A119.1C11B—C12B—C7B121.3 (2)
C5A—C4A—C3A120.8 (3)N2B—C13B—C9B123.7 (2)
C5A—C4A—H4A119.6N2B—C13B—H13B118.1
C3A—C4A—H4A119.6C9B—C13B—H13B118.1
C4A—C5A—C6A118.9 (2)N2B—C14B—C15B123.8 (2)
C4A—C5A—H5A120.6N2B—C14B—S1B126.62 (18)
C6A—C5A—H5A120.6C15B—C14B—S1B109.55 (19)
C5A—C6A—C1A119.5 (2)C14B—C15B—C16B114.1 (2)
C5A—C6A—C7A133.6 (2)C14B—C15B—C24B122.1 (2)
C1A—C6A—C7A106.86 (19)C16B—C15B—C24B123.8 (2)
C8A—C7A—C12A119.4 (2)C21B—C16B—C15B112.4 (2)
C8A—C7A—C6A134.4 (2)C21B—C16B—C17B122.7 (2)
C12A—C7A—C6A106.16 (18)C15B—C16B—C17B125.0 (3)
C7A—C8A—C9A119.5 (2)C18B—C17B—C16B114.8 (4)
C7A—C8A—H8A120.2C16B—C17B—C18X105.1 (4)
C9A—C8A—H8A120.2C18B—C17B—H17C108.6
C8A—C9A—C10A119.5 (2)C16B—C17B—H17C108.6
C8A—C9A—C13A121.9 (2)C18X—C17B—H17C88.7
C10A—C9A—C13A118.6 (2)C18B—C17B—H17D108.6
C11A—C10A—C9A122.5 (2)C16B—C17B—H17D108.6
C11A—C10A—H10A118.8C18X—C17B—H17D134.9
C9A—C10A—H10A118.8H17C—C17B—H17D107.5
C10A—C11A—C12A117.4 (2)C18B—C17B—H17E80.2
C10A—C11A—H11A121.3C16B—C17B—H17E111.5
C12A—C11A—H11A121.3C18X—C17B—H17E108.0
N1A—C12A—C11A129.0 (2)H17C—C17B—H17E130.0
N1A—C12A—C7A109.28 (19)C18B—C17B—H17F125.3
C11A—C12A—C7A121.7 (2)C16B—C17B—H17F110.9
N2A—C13A—C9A123.9 (2)C18X—C17B—H17F112.0
N2A—C13A—H13A118.0H17D—C17B—H17F82.7
C9A—C13A—H13A118.0H17E—C17B—H17F109.3
C15A—C14A—N2A124.4 (2)C17B—C18B—C19B105.3 (5)
C15A—C14A—S1A109.76 (16)C17B—C18B—H18C110.7
N2A—C14A—S1A125.85 (18)C19B—C18B—H18C110.7
C14A—C15A—C24A123.3 (2)C17B—C18B—H18D110.7
C14A—C15A—C16A114.2 (2)C19B—C18B—H18D110.7
C24A—C15A—C16A122.5 (2)H18C—C18B—H18D108.8
C21A—C16A—C15A112.0 (2)C18B—C19B—C20B116.5 (6)
C21A—C16A—C17A122.6 (2)C18B—C19B—H19C108.2
C15A—C16A—C17A125.3 (2)C20B—C19B—H19C108.2
C16A—C17A—C18A111.3 (2)C18B—C19B—H19D108.2
C16A—C17A—H17A109.4C20B—C19B—H19D108.2
C18A—C17A—H17A109.4H19C—C19B—H19D107.3
C16A—C17A—H17B109.4C19X—C18X—C17B121.8 (7)
C18A—C17A—H17B109.4C19X—C18X—H18E106.9
H17A—C17A—H17B108.0C17B—C18X—H18E106.9
C19A—C18A—C17A113.3 (3)C19X—C18X—H18F106.9
C19A—C18A—H18A108.9C17B—C18X—H18F106.9
C17A—C18A—H18A108.9H18E—C18X—H18F106.7
C19A—C18A—H18B108.9C20B—C19X—C18X101.7 (7)
C17A—C18A—H18B108.9C20B—C19X—H19E111.4
H18A—C18A—H18B107.7C18X—C19X—H19E111.4
C18A—C19A—C20A114.3 (2)C20B—C19X—H19F111.4
C18A—C19A—H19A108.7C18X—C19X—H19F111.4
C20A—C19A—H19A108.7H19E—C19X—H19F109.3
C18A—C19A—H19B108.7C21B—C20B—C19X116.9 (4)
C20A—C19A—H19B108.7C21B—C20B—C19B103.9 (4)
H19A—C19A—H19B107.6C21B—C20B—H20C111.0
C21A—C20A—C19A109.7 (2)C19X—C20B—H20C124.8
C21A—C20A—H20A109.7C19B—C20B—H20C111.0
C19A—C20A—H20A109.7C21B—C20B—H20D111.0
C21A—C20A—H20B109.7C19X—C20B—H20D78.1
C19A—C20A—H20B109.7C19B—C20B—H20D111.0
H20A—C20A—H20B108.2H20C—C20B—H20D109.0
C16A—C21A—C20A124.9 (2)C21B—C20B—H20E107.9
C16A—C21A—S1A112.23 (17)C19X—C20B—H20E108.1
C20A—C21A—S1A122.78 (19)C19B—C20B—H20E85.4
N1A—C22A—C23A113.3 (2)H20D—C20B—H20E131.9
N1A—C22A—H22A108.9C21B—C20B—H20F106.7
C23A—C22A—H22A108.9C19X—C20B—H20F109.8
N1A—C22A—H22B108.9C19B—C20B—H20F141.1
C23A—C22A—H22B108.9H20C—C20B—H20F79.6
H22A—C22A—H22B107.7H20E—C20B—H20F107.0
C22A—C23A—H23A109.5C16B—C21B—C20B125.5 (2)
C22A—C23A—H23B109.5C16B—C21B—S1B112.0 (2)
H23A—C23A—H23B109.5C20B—C21B—S1B122.5 (2)
C22A—C23A—H23C109.5N1B—C22B—C23B112.2 (2)
H23A—C23A—H23C109.5N1B—C22B—H22C109.2
H23B—C23A—H23C109.5C23B—C22B—H22C109.2
N3A—C24A—C15A177.1 (3)N1B—C22B—H22D109.2
C21B—S1B—C14B91.95 (13)C23B—C22B—H22D109.2
C12B—N1B—C1B108.69 (19)H22C—C22B—H22D107.9
C12B—N1B—C22B126.4 (2)C22B—C23B—H23D109.5
C1B—N1B—C22B124.1 (2)C22B—C23B—H23E109.5
C13B—N2B—C14B120.0 (2)H23D—C23B—H23E109.5
C2B—C1B—N1B129.3 (2)C22B—C23B—H23F109.5
C2B—C1B—C6B121.9 (2)H23D—C23B—H23F109.5
N1B—C1B—C6B108.8 (2)H23E—C23B—H23F109.5
C3B—C2B—C1B117.5 (2)N3B—C24B—C15B177.2 (3)
C3B—C2B—H2B121.3C26—C25—C30120.7 (4)
C1B—C2B—H2B121.3C26—C25—H25A119.6
C2B—C3B—C4B121.5 (2)C30—C25—H25A119.6
C2B—C3B—H3B119.2C25—C26—C27117.5 (4)
C4B—C3B—H3B119.2C25—C26—H26A121.3
C5B—C4B—C3B121.0 (3)C27—C26—H26A121.3
C5B—C4B—H4B119.5C28—C27—C26122.7 (4)
C3B—C4B—H4B119.5C28—C27—H27A118.6
C4B—C5B—C6B118.9 (2)C26—C27—H27A118.6
C4B—C5B—H5B120.6C27—C28—C29118.8 (4)
C6B—C5B—H5B120.6C27—C28—H28A120.6
C5B—C6B—C1B119.1 (2)C29—C28—H28A120.6
C5B—C6B—C7B134.2 (2)C30—C29—C28118.9 (4)
C1B—C6B—C7B106.6 (2)C30—C29—H29A120.6
C8B—C7B—C12B119.1 (2)C28—C29—H29A120.6
C8B—C7B—C6B134.4 (2)C25—C30—C29121.3 (4)
C12B—C7B—C6B106.5 (2)C25—C30—H30A119.4
C7B—C8B—C9B120.4 (2)C29—C30—H30A119.4
C12A—N1A—C1A—C2A176.3 (2)C4B—C5B—C6B—C1B0.5 (3)
C22A—N1A—C1A—C2A4.7 (4)C4B—C5B—C6B—C7B176.9 (2)
C12A—N1A—C1A—C6A1.4 (2)C2B—C1B—C6B—C5B0.4 (3)
C22A—N1A—C1A—C6A177.6 (2)N1B—C1B—C6B—C5B179.32 (19)
N1A—C1A—C2A—C3A177.1 (2)C2B—C1B—C6B—C7B177.7 (2)
C6A—C1A—C2A—C3A0.4 (4)N1B—C1B—C6B—C7B1.3 (2)
C1A—C2A—C3A—C4A1.8 (4)C5B—C6B—C7B—C8B0.7 (4)
C2A—C3A—C4A—C5A1.4 (4)C1B—C6B—C7B—C8B178.4 (2)
C3A—C4A—C5A—C6A0.6 (4)C5B—C6B—C7B—C12B178.0 (2)
C4A—C5A—C6A—C1A2.0 (4)C1B—C6B—C7B—C12B0.4 (2)
C4A—C5A—C6A—C7A176.8 (2)C12B—C7B—C8B—C9B0.9 (3)
N1A—C1A—C6A—C5A179.5 (2)C6B—C7B—C8B—C9B177.7 (2)
C2A—C1A—C6A—C5A1.6 (3)C7B—C8B—C9B—C10B1.6 (3)
N1A—C1A—C6A—C7A0.4 (2)C7B—C8B—C9B—C13B178.2 (2)
C2A—C1A—C6A—C7A177.5 (2)C8B—C9B—C10B—C11B1.2 (4)
C5A—C6A—C7A—C8A2.7 (4)C13B—C9B—C10B—C11B178.6 (2)
C1A—C6A—C7A—C8A178.4 (2)C9B—C10B—C11B—C12B0.0 (4)
C5A—C6A—C7A—C12A178.2 (3)C1B—N1B—C12B—C11B178.5 (2)
C1A—C6A—C7A—C12A0.7 (2)C22B—N1B—C12B—C11B8.5 (4)
C12A—C7A—C8A—C9A1.7 (3)C1B—N1B—C12B—C7B1.4 (2)
C6A—C7A—C8A—C9A179.3 (2)C22B—N1B—C12B—C7B171.4 (2)
C7A—C8A—C9A—C10A0.3 (3)C10B—C11B—C12B—N1B179.2 (2)
C7A—C8A—C9A—C13A178.8 (2)C10B—C11B—C12B—C7B0.7 (3)
C8A—C9A—C10A—C11A1.6 (4)C8B—C7B—C12B—N1B179.6 (2)
C13A—C9A—C10A—C11A177.5 (2)C6B—C7B—C12B—N1B0.6 (2)
C9A—C10A—C11A—C12A0.8 (4)C8B—C7B—C12B—C11B0.3 (3)
C1A—N1A—C12A—C11A177.9 (2)C6B—C7B—C12B—C11B179.3 (2)
C22A—N1A—C12A—C11A3.1 (4)C14B—N2B—C13B—C9B180.0 (2)
C1A—N1A—C12A—C7A1.9 (2)C8B—C9B—C13B—N2B176.5 (2)
C22A—N1A—C12A—C7A177.1 (2)C10B—C9B—C13B—N2B3.3 (4)
C10A—C11A—C12A—N1A179.0 (2)C13B—N2B—C14B—C15B177.0 (2)
C10A—C11A—C12A—C7A1.3 (3)C13B—N2B—C14B—S1B2.7 (3)
C8A—C7A—C12A—N1A177.68 (19)C21B—S1B—C14B—N2B179.4 (2)
C6A—C7A—C12A—N1A1.6 (2)C21B—S1B—C14B—C15B0.92 (19)
C8A—C7A—C12A—C11A2.5 (3)N2B—C14B—C15B—C16B179.5 (2)
C6A—C7A—C12A—C11A178.2 (2)S1B—C14B—C15B—C16B0.9 (3)
C14A—N2A—C13A—C9A175.7 (2)N2B—C14B—C15B—C24B0.9 (4)
C8A—C9A—C13A—N2A8.2 (4)S1B—C14B—C15B—C24B178.80 (19)
C10A—C9A—C13A—N2A170.9 (2)C14B—C15B—C16B—C21B0.3 (3)
C13A—N2A—C14A—C15A177.1 (2)C24B—C15B—C16B—C21B179.4 (2)
C13A—N2A—C14A—S1A4.6 (3)C14B—C15B—C16B—C17B178.6 (2)
C21A—S1A—C14A—C15A0.84 (18)C24B—C15B—C16B—C17B1.8 (4)
C21A—S1A—C14A—N2A177.6 (2)C21B—C16B—C17B—C18B14.7 (5)
N2A—C14A—C15A—C24A1.4 (4)C15B—C16B—C17B—C18B166.5 (4)
S1A—C14A—C15A—C24A179.89 (19)C21B—C16B—C17B—C18X13.2 (5)
N2A—C14A—C15A—C16A177.8 (2)C15B—C16B—C17B—C18X165.6 (4)
S1A—C14A—C15A—C16A0.7 (2)C16B—C17B—C18B—C19B43.5 (8)
C14A—C15A—C16A—C21A0.1 (3)C18X—C17B—C18B—C19B31.3 (8)
C24A—C15A—C16A—C21A179.3 (2)C17B—C18B—C19B—C20B66.4 (10)
C14A—C15A—C16A—C17A177.5 (2)C18B—C17B—C18X—C19X66.9 (11)
C24A—C15A—C16A—C17A1.7 (4)C16B—C17B—C18X—C19X48.0 (10)
C21A—C16A—C17A—C18A16.2 (4)C17B—C18X—C19X—C20B61.3 (13)
C15A—C16A—C17A—C18A161.2 (2)C18X—C19X—C20B—C21B40.4 (10)
C16A—C17A—C18A—C19A44.0 (4)C18X—C19X—C20B—C19B32.8 (6)
C17A—C18A—C19A—C20A58.4 (4)C18B—C19B—C20B—C21B50.9 (8)
C18A—C19A—C20A—C21A39.9 (3)C18B—C19B—C20B—C19X67.6 (9)
C15A—C16A—C21A—C20A176.8 (2)C15B—C16B—C21B—C20B178.8 (2)
C17A—C16A—C21A—C20A0.9 (4)C17B—C16B—C21B—C20B0.1 (4)
C15A—C16A—C21A—S1A0.6 (3)C15B—C16B—C21B—S1B0.4 (3)
C17A—C16A—C21A—S1A178.22 (18)C17B—C16B—C21B—S1B179.31 (19)
C19A—C20A—C21A—C16A11.9 (4)C19X—C20B—C21B—C16B16.1 (7)
C19A—C20A—C21A—S1A171.02 (19)C19B—C20B—C21B—C16B16.2 (4)
C14A—S1A—C21A—C16A0.81 (19)C19X—C20B—C21B—S1B164.8 (5)
C14A—S1A—C21A—C20A176.6 (2)C19B—C20B—C21B—S1B162.9 (3)
C12A—N1A—C22A—C23A90.5 (3)C14B—S1B—C21B—C16B0.8 (2)
C1A—N1A—C22A—C23A90.7 (3)C14B—S1B—C21B—C20B178.4 (2)
C12B—N1B—C1B—C2B177.2 (2)C12B—N1B—C22B—C23B89.1 (3)
C22B—N1B—C1B—C2B6.9 (4)C1B—N1B—C22B—C23B79.4 (3)
C12B—N1B—C1B—C6B1.7 (2)C30—C25—C26—C272.0 (7)
C22B—N1B—C1B—C6B171.9 (2)C25—C26—C27—C281.3 (7)
N1B—C1B—C2B—C3B178.7 (2)C26—C27—C28—C292.8 (7)
C6B—C1B—C2B—C3B0.0 (3)C27—C28—C29—C301.0 (6)
C1B—C2B—C3B—C4B0.2 (4)C26—C25—C30—C293.8 (6)
C2B—C3B—C4B—C5B0.1 (4)C28—C29—C30—C252.2 (6)
C3B—C4B—C5B—C6B0.3 (4)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C1B–C6B, C7A–C12A and C14A–C16A/C21A/S1A rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22A—H22A···N3Bi0.972.593.487 (3)155
C11A—H11A···Cg1ii0.932.653.499 (3)153
C11B—H11B···Cg2i0.932.823.725 (3)166
C27—H27A···Cg3iii0.932.713.625 (6)169
Symmetry codes: (i) x+1, y+2, z; (ii) x1, y, z; (iii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formula2C24H21N3S·C6H6
Mr845.10
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)11.4816 (1), 13.7322 (2), 14.8358 (2)
α, β, γ (°)81.841 (1), 77.083 (1), 83.864 (1)
V3)2250.00 (5)
Z2
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.45 × 0.15 × 0.07
Data collection
DiffractometerBruker SMART APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.931, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections
48693, 13169, 6227
Rint0.048
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.070, 0.167, 1.01
No. of reflections13169
No. of parameters580
No. of restraints63
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.20

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

Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C1B–C6B, C7A–C12A and C14A–C16A/C21A/S1A rings, respectively.
D—H···AD—HH···AD···AD—H···A
C22A—H22A···N3Bi0.972.593.487 (3)155
C11A—H11A···Cg1ii0.932.653.499 (3)153
C11B—H11B···Cg2i0.932.823.725 (3)166
C27—H27A···Cg3iii0.932.713.625 (6)169
Symmetry codes: (i) x+1, y+2, z; (ii) x1, y, z; (iii) x, y+1, z+1.
 

Footnotes

Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

On secondment from: The Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, Saudi Arabia.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). JHG also thanks USM for the award of a USM fellowship. The authors thank the Department of Chemistry, King Abdulaziz University, for providing research facilities.

References

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Volume 66| Part 5| May 2010| Pages o1200-o1201
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