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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): o354.
Published online 2009 January 23. doi:  10.1107/S160053680900186X
PMCID: PMC2968328

1,2-Di-2-quinolylethene

Abstract

The title compound, C20H14N2, comprises two crystallographically independent centrosymmetric mol­ecules (A and B) with different conformations due to the disorder of molecule B. The whole of mol­ecule B is disordered over two sets of positions, corresponding to a 180° rotation of the molecule, with a site-occupancy ratio of 0.780 (6):0.220 (6). The minor component of the disordered part in B has the same configuration as mol­ecule A, but the major component is different. The dihedral angle between the planes of mol­ecule A and mol­ecule B (major component) is 63.22 (3)°. The crystal structure is stabilized by inter­molecular C—H(...)π inter­actions.

Related literature

For the biological activities, mol­ecular recognition and catalysis see, for example: Fournet et al. (2003 [triangle]); Yamada et al., (1981 [triangle]); Goswami & Mahapatra (1998 [triangle]); Goswami et al. (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o354-scheme1.jpg

Experimental

Crystal data

  • C20H14N2
  • M r = 282.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o354-efi1.jpg
  • a = 15.6378 (2) Å
  • b = 6.0798 (1) Å
  • c = 16.0860 (2) Å
  • β = 108.879 (1)°
  • V = 1447.10 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100.0 (1) K
  • 0.34 × 0.33 × 0.09 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.863, T max = 0.993
  • 12910 measured reflections
  • 3317 independent reflections
  • 2476 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.102
  • S = 1.04
  • 3317 reflections
  • 245 parameters
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900186X/pk2144sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900186X/pk2144Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. We thank the DST [SR/S1/OC-13/2005], Goverment of India, for financial support. ACM thanks the UGC, Goverment of India, for a fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Alkene or alkyne substituted quinolines are important as they exhibit significant activities against HTLV-1 transformed cells and also show the efficiency of these compounds for the treatment of ATLL (Fournet et al., 2003).

The benzylic carbon-carbon coupling reactions of benzylic halides catalyzed by CoI(PPh3)3Cl and also the synthesis of diaryl ethylene have been reported (Yamada et al., 1981). The same reaction of functionalised benzylic bromides was shown to be useful for carbon-carbon bond formation by CoI in the absence of oxygen, resulting in the convenient synthesis of a variety of functionalized benzylic dimers suitable for new spacers in molecular recognition research (Goswami & Mahapatra 1998; Goswami et al., 1989). We report here a useful and straightforward procedure for the synthesis of 1,2-di-(2-quinolyl)-ethylene from 2,2-dichloromethyl quinoline.

The title compound, Fig. 1, comprises two crystallographically independent centrosymmetric molecules with different conformations due to the disorder over two sites, corresponding to a ca180° rotation about the C9B—C10B bond. The minor component of the disordered part in B has the same configuration as molecule A, but the major component is different. The difference in conformation is that the A molecule atoms N1A-C9A-C10A-C10AA (AA is the symmetry related of A), form a chain like U shape while the corresponding atoms in the major component of B form a Z shape. The dihedral angle between the plane of molecule A and molecule B is 63.22 (3)°. In molecule B, the whole molecule is disordered over two positions with a site-occupancy factor of 0.780 (6)/0.220 (6). The crystal structure is stabilized by intermolecular C—H···π interactions (C2A—H2AA···Cg1i, C6A—H6AA···Cg2ii, C4B—H4B···Cg3iii, and C6A—H6AA···Cg3iv: (i) 1/2 - X, 1/2 + Y, 1/2 - Z; (ii) -1/2 + X, 1/2 - Y, 1/2 + Z; (iii) 1/2 + X, 3/2 - Y, 1/2 + Z; (iv) 1/2 - X, -3/2 + Y, 1/2 - Z; Cg1, Cg2 and Cg3 are the centroids of the C3A–C8A, N1B/C8B/C3B/C2B/C1B/C9B and N1C/C8C/C3C/C2C/C1C/C9C aromatic rings).

Experimental

2,2-dichloromethyl quinoline (1 mmol) was dissolved in dry benzene (25 mL). The anhydrous green colored CoI(PPh3)3Cl (2.5 mmol) catalyst was added to the reaction mixture with stirring at room temperature under a nitrogen atmosphere. After 30 minutes, the color of the reaction mixture had changed from green to blue. The reaction mixture was then heated under reflux conditions for 2-3 h. The solvent was evaporated to dryness, the residue was worked up with water and the organic part was extracted with chloroform. The organic layer was dried (Na2SO4) and concentrated. Column chromatography of the crude product on silica gel and elution with methanol in chloroform afforded 1,2-di-(2-quinolyl)-ethylene. Single crystals suitable for X-ray diffraction were grown by slow evaporation of a CHCl3-methanol (1:1) solution of the title compound.

Refinement

All of the hydrogen atoms were positioned geometrically and constrained to refine with the parent atoms with C—H = 0.96 Å and Uiso (H) = 1.2 Ueq (C). The whole molecule B is disordered by a 180° rotation over two positions with a site- occupancy factor of 0.780 (6)/0.220 (6). For the minor component, only isotropic refinement was used. Initially rigid, similarity and simulation restraints were applied to molecule B. After steady state has been reached, these restraints were removed for the final refinement. There is no restraint used in the final refinement.

Figures

Fig. 1.
The molecular structure showing 40% probability displacement ellipsoids and the atomic numbering. Open bonds indicate the minor component [symmetry code for C: -x + 1, -y + 2, -z and symmetry code for unlabelled atoms -x, -y, -z].
Fig. 2.
Crystal packing of viewed down the b-axis showing linking of molecules by intermolecular C—H···π interactions. Inermolecular interactions are drawn as dashed lines. Only the major component of the disordered molecule ...

Crystal data

C20H14N2F(000) = 592
Mr = 282.33Dx = 1.296 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3767 reflections
a = 15.6378 (2) Åθ = 2.7–31.5°
b = 6.0798 (1) ŵ = 0.08 mm1
c = 16.0860 (2) ÅT = 100 K
β = 108.879 (1)°Block, yellow
V = 1447.10 (4) Å30.34 × 0.33 × 0.09 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer3317 independent reflections
Radiation source: fine-focus sealed tube2476 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 27.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −20→20
Tmin = 0.863, Tmax = 0.993k = −7→6
12910 measured reflectionsl = −20→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.102w = 1/[σ2(Fo2) + (0.0416P)2 + 0.3849P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3317 reflectionsΔρmax = 0.25 e Å3
245 parametersΔρmin = −0.17 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0035 (10)

Special details

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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)

xyzUiso*/UeqOcc. (<1)
N1A0.07166 (7)0.04930 (18)0.16586 (7)0.0216 (3)
C1A0.10529 (8)0.3931 (2)0.10857 (9)0.0246 (3)
H1AA0.10030.47970.05960.030*
C2A0.14983 (8)0.4706 (2)0.19043 (9)0.0247 (3)
H2AA0.17490.61080.19770.030*
C3A0.15781 (8)0.3371 (2)0.26439 (8)0.0215 (3)
C4A0.20530 (8)0.4010 (2)0.35202 (9)0.0263 (3)
H4AA0.23180.53950.36310.032*
C5A0.21245 (8)0.2605 (2)0.42038 (9)0.0281 (3)
H5AA0.24420.30330.47760.034*
C6A0.17178 (9)0.0509 (2)0.40428 (9)0.0281 (3)
H6AA0.1770−0.04370.45110.034*
C7A0.12485 (8)−0.0149 (2)0.32079 (9)0.0248 (3)
H7AA0.0977−0.15280.31140.030*
C8A0.11711 (8)0.1247 (2)0.24836 (8)0.0201 (3)
C9A0.06639 (8)0.1799 (2)0.09801 (8)0.0218 (3)
C10A0.01868 (8)0.0993 (2)0.00925 (8)0.0232 (3)
H10A0.01420.1934−0.03750.028*
N1B0.69538 (18)0.8831 (3)0.07847 (10)0.0206 (5)0.780 (6)
C1B0.57855 (14)0.6355 (5)0.08990 (15)0.0210 (5)0.780 (6)
H1B0.51740.61040.08010.025*0.780 (6)
C2B0.6415 (3)0.4802 (7)0.1311 (3)0.0247 (9)0.780 (6)
H2B0.62310.34760.14860.030*0.780 (6)
C3B0.7367 (3)0.5221 (6)0.1476 (2)0.0161 (7)0.780 (6)
C4B0.8065 (3)0.3683 (7)0.1894 (3)0.0215 (9)0.780 (6)
H4B0.79180.23210.20720.026*0.780 (6)
C5B0.89117 (17)0.4192 (6)0.20252 (17)0.0241 (6)0.780 (6)
H5B0.93600.31670.22840.029*0.780 (6)
C6B0.91586 (16)0.6283 (5)0.17789 (16)0.0236 (6)0.780 (6)
H6B0.97650.66230.18910.028*0.780 (6)
C7B0.8505 (2)0.7811 (4)0.13753 (16)0.0219 (5)0.780 (6)
H7B0.86700.91740.12130.026*0.780 (6)
C8B0.7575 (3)0.7292 (7)0.1208 (2)0.0182 (7)0.780 (6)
C9B0.6082 (2)0.8361 (4)0.06227 (11)0.0192 (5)0.780 (6)
C10B0.54504 (13)1.0039 (3)0.01229 (11)0.0208 (6)0.780 (6)
H10B0.57031.1285−0.00390.025*0.780 (6)
N1C0.3376 (6)1.1411 (12)−0.0755 (4)0.0140 (16)*0.220 (6)
C1C0.4292 (7)1.4289 (18)−0.1047 (6)0.026 (2)*0.220 (6)
H1C0.48701.4748−0.10130.031*0.220 (6)
C2C0.3606 (11)1.556 (3)−0.1416 (11)0.014 (3)*0.220 (6)
H2C0.36871.6944−0.16280.017*0.220 (6)
C3C0.2813 (9)1.486 (2)−0.1479 (10)0.011 (3)*0.220 (6)
C4C0.2057 (13)1.604 (3)−0.1817 (12)0.024 (4)*0.220 (6)
H4C0.21201.7485−0.19760.029*0.220 (6)
C5C0.1046 (7)1.515 (2)−0.1969 (7)0.020 (3)*0.220 (6)
H5C0.05291.5947−0.22630.025*0.220 (6)
C6C0.1025 (8)1.3099 (17)−0.1622 (6)0.022 (2)*0.220 (6)
H6C0.04741.2482−0.16450.026*0.220 (6)
C7C0.1792 (8)1.197 (2)−0.1248 (6)0.026 (3)*0.220 (6)
H7C0.17431.0569−0.10350.031*0.220 (6)
C8C0.2620 (12)1.271 (4)−0.1160 (13)0.030 (5)*0.220 (6)
C9C0.4178 (6)1.2225 (17)−0.0697 (5)0.0172 (18)*0.220 (6)
C10C0.4987 (5)1.0882 (12)−0.0238 (4)0.023 (2)*0.220 (6)
H10C0.55331.1342−0.02940.028*0.220 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N1A0.0207 (5)0.0220 (6)0.0214 (6)0.0007 (4)0.0058 (4)−0.0004 (5)
C1A0.0220 (6)0.0249 (7)0.0272 (7)0.0016 (5)0.0083 (5)0.0051 (6)
C2A0.0214 (6)0.0195 (7)0.0330 (8)−0.0017 (5)0.0084 (6)−0.0009 (6)
C3A0.0174 (6)0.0220 (7)0.0253 (7)0.0022 (5)0.0072 (5)−0.0030 (5)
C4A0.0227 (6)0.0248 (7)0.0301 (8)0.0003 (5)0.0068 (5)−0.0085 (6)
C5A0.0248 (7)0.0365 (8)0.0213 (7)0.0032 (6)0.0052 (5)−0.0089 (6)
C6A0.0282 (7)0.0344 (8)0.0222 (7)0.0036 (6)0.0088 (5)0.0023 (6)
C7A0.0250 (7)0.0245 (7)0.0251 (7)−0.0009 (5)0.0083 (5)0.0005 (6)
C8A0.0163 (6)0.0215 (7)0.0226 (7)0.0012 (5)0.0064 (5)−0.0013 (5)
C9A0.0189 (6)0.0225 (7)0.0236 (7)0.0022 (5)0.0065 (5)0.0017 (5)
C10A0.0214 (6)0.0265 (7)0.0209 (7)0.0029 (5)0.0058 (5)0.0034 (6)
N1B0.0168 (11)0.0220 (9)0.0217 (8)−0.0001 (7)0.0045 (7)0.0001 (6)
C1B0.0193 (9)0.0226 (15)0.0203 (10)−0.0011 (9)0.0051 (7)−0.0014 (10)
C2B0.0308 (15)0.0216 (19)0.0228 (16)−0.0083 (12)0.0103 (11)−0.0013 (13)
C3B0.0110 (15)0.0222 (13)0.0160 (11)−0.0003 (12)0.0056 (11)−0.0020 (7)
C4B0.0253 (17)0.0185 (15)0.0189 (14)0.0117 (12)0.0048 (11)0.0069 (10)
C5B0.0255 (12)0.0219 (15)0.0244 (11)0.0049 (11)0.0074 (8)0.0034 (11)
C6B0.0194 (11)0.0273 (14)0.0233 (11)0.0025 (11)0.0057 (8)0.0023 (10)
C7B0.0179 (13)0.0234 (11)0.0258 (11)−0.0020 (11)0.0089 (10)−0.0010 (9)
C8B0.022 (2)0.0188 (13)0.0133 (12)0.0004 (14)0.0051 (12)−0.0022 (7)
C9B0.0188 (11)0.0192 (11)0.0195 (9)−0.0017 (9)0.0061 (8)−0.0012 (7)
C10B0.0214 (11)0.0190 (10)0.0214 (9)−0.0012 (7)0.0061 (7)0.0009 (7)

Geometric parameters (Å, °)

N1A—C9A1.3307 (16)C4B—H4B0.9300
N1A—C8A1.3661 (15)C5B—C6B1.422 (4)
C1A—C2A1.3592 (18)C5B—H5B0.9300
C1A—C9A1.4183 (18)C6B—C7B1.378 (3)
C1A—H1AA0.9300C6B—H6B0.9300
C2A—C3A1.4118 (18)C7B—C8B1.426 (5)
C2A—H2AA0.9300C7B—H7B0.9300
C3A—C4A1.4183 (17)C9B—C10B1.466 (3)
C3A—C8A1.4259 (18)C10B—C10Bii1.335 (4)
C4A—C5A1.3683 (19)C10B—H10B0.9300
C4A—H4AA0.9300N1C—C9C1.324 (9)
C5A—C6A1.411 (2)N1C—C8C1.40 (2)
C5A—H5AA0.9300C1C—C2C1.30 (2)
C6A—C7A1.3652 (18)C1C—C9C1.410 (10)
C6A—H6AA0.9300C1C—H1C0.9300
C7A—C8A1.4146 (18)C2C—C3C1.28 (2)
C7A—H7AA0.9300C2C—H2C0.9300
C9A—C10A1.4650 (17)C3C—C4C1.34 (2)
C10A—C10Ai1.332 (3)C3C—C8C1.47 (3)
C10A—H10A0.9300C4C—C5C1.61 (2)
N1B—C9B1.333 (3)C4C—H4C0.9300
N1B—C8B1.362 (5)C5C—C6C1.371 (13)
C1B—C2B1.370 (5)C5C—H5C0.9300
C1B—C9B1.426 (3)C6C—C7C1.344 (11)
C1B—H1B0.9300C6C—H6C0.9300
C2B—C3B1.448 (6)C7C—C8C1.335 (18)
C2B—H2B0.9300C7C—H7C0.9300
C3B—C8B1.403 (6)C9C—C10C1.486 (11)
C3B—C4B1.429 (5)C10C—C10Cii1.311 (15)
C4B—C5B1.308 (6)C10C—H10C0.9300
C9A—N1A—C8A118.11 (11)C7B—C6B—C5B120.5 (2)
C2A—C1A—C9A119.88 (12)C7B—C6B—H6B119.8
C2A—C1A—H1AA120.1C5B—C6B—H6B119.8
C9A—C1A—H1AA120.1C6B—C7B—C8B119.7 (2)
C1A—C2A—C3A119.68 (12)C6B—C7B—H7B120.2
C1A—C2A—H2AA120.2C8B—C7B—H7B120.2
C3A—C2A—H2AA120.2N1B—C8B—C3B124.8 (4)
C2A—C3A—C4A123.73 (12)N1B—C8B—C7B117.5 (3)
C2A—C3A—C8A117.09 (11)C3B—C8B—C7B117.7 (3)
C4A—C3A—C8A119.16 (12)N1B—C9B—C1B122.53 (17)
C5A—C4A—C3A120.54 (13)N1B—C9B—C10B115.0 (2)
C5A—C4A—H4AA119.7C1B—C9B—C10B122.4 (2)
C3A—C4A—H4AA119.7C10Bii—C10B—C9B126.7 (2)
C4A—C5A—C6A120.12 (12)C10Bii—C10B—H10B116.7
C4A—C5A—H5AA119.9C9B—C10B—H10B116.7
C6A—C5A—H5AA119.9C9C—N1C—C8C117.5 (11)
C7A—C6A—C5A120.80 (13)C2C—C1C—C9C121.4 (10)
C7A—C6A—H6AA119.6C2C—C1C—H1C119.3
C5A—C6A—H6AA119.6C9C—C1C—H1C119.3
C6A—C7A—C8A120.67 (13)C3C—C2C—C1C118.0 (14)
C6A—C7A—H7AA119.7C3C—C2C—H2C121.0
C8A—C7A—H7AA119.7C1C—C2C—H2C121.0
N1A—C8A—C7A118.54 (12)C2C—C3C—C4C123.7 (16)
N1A—C8A—C3A122.77 (12)C2C—C3C—C8C124.9 (14)
C7A—C8A—C3A118.69 (11)C4C—C3C—C8C111.4 (14)
N1A—C9A—C1A122.47 (12)C3C—C4C—C5C125.1 (14)
N1A—C9A—C10A118.44 (12)C3C—C4C—H4C117.5
C1A—C9A—C10A119.09 (12)C5C—C4C—H4C117.5
C10Ai—C10A—C9A124.71 (15)C6C—C5C—C4C113.2 (10)
C10Ai—C10A—H10A117.6C6C—C5C—H5C123.4
C9A—C10A—H10A117.6C4C—C5C—H5C123.4
C9B—N1B—C8B118.0 (3)C7C—C6C—C5C120.8 (11)
C2B—C1B—C9B119.0 (2)C7C—C6C—H6C119.6
C2B—C1B—H1B120.5C5C—C6C—H6C119.6
C9B—C1B—H1B120.5C8C—C7C—C6C124.7 (14)
C1B—C2B—C3B120.2 (3)C8C—C7C—H7C117.7
C1B—C2B—H2B119.9C6C—C7C—H7C117.7
C3B—C2B—H2B119.9C7C—C8C—N1C120.2 (18)
C8B—C3B—C4B120.9 (4)C7C—C8C—C3C124.4 (16)
C8B—C3B—C2B115.4 (4)N1C—C8C—C3C115.3 (14)
C4B—C3B—C2B123.7 (4)N1C—C9C—C1C122.9 (8)
C5B—C4B—C3B120.0 (4)N1C—C9C—C10C117.7 (9)
C5B—C4B—H4B120.0C1C—C9C—C10C119.3 (9)
C3B—C4B—H4B120.0C10Cii—C10C—C9C126.9 (9)
C4B—C5B—C6B121.2 (3)C10Cii—C10C—H10C116.6
C4B—C5B—H5B119.4C9C—C10C—H10C116.6
C6B—C5B—H5B119.4
C9A—C1A—C2A—C3A0.64 (18)C2B—C3B—C8B—N1B−2.9 (5)
C1A—C2A—C3A—C4A178.00 (12)C4B—C3B—C8B—C7B−0.6 (5)
C1A—C2A—C3A—C8A−0.46 (17)C2B—C3B—C8B—C7B178.5 (3)
C2A—C3A—C4A—C5A−178.12 (12)C6B—C7B—C8B—N1B−178.1 (2)
C8A—C3A—C4A—C5A0.32 (18)C6B—C7B—C8B—C3B0.6 (4)
C3A—C4A—C5A—C6A−0.58 (19)C8B—N1B—C9B—C1B2.0 (3)
C4A—C5A—C6A—C7A−0.06 (19)C8B—N1B—C9B—C10B−176.8 (2)
C5A—C6A—C7A—C8A0.96 (19)C2B—C1B—C9B—N1B−3.1 (3)
C9A—N1A—C8A—C7A−178.59 (11)C2B—C1B—C9B—C10B175.6 (3)
C9A—N1A—C8A—C3A0.75 (17)N1B—C9B—C10B—C10Bii179.9 (2)
C6A—C7A—C8A—N1A178.17 (11)C1B—C9B—C10B—C10Bii1.1 (3)
C6A—C7A—C8A—C3A−1.20 (18)C9C—C1C—C2C—C3C−2(2)
C2A—C3A—C8A—N1A−0.24 (17)C1C—C2C—C3C—C4C177.6 (16)
C4A—C3A—C8A—N1A−178.78 (11)C1C—C2C—C3C—C8C0(3)
C2A—C3A—C8A—C7A179.10 (11)C2C—C3C—C4C—C5C175.5 (15)
C4A—C3A—C8A—C7A0.56 (17)C8C—C3C—C4C—C5C−7(2)
C8A—N1A—C9A—C1A−0.58 (17)C3C—C4C—C5C—C6C7(2)
C8A—N1A—C9A—C10A179.29 (10)C4C—C5C—C6C—C7C−3.8 (16)
C2A—C1A—C9A—N1A−0.11 (19)C5C—C6C—C7C—C8C2(2)
C2A—C1A—C9A—C10A−179.98 (11)C6C—C7C—C8C—N1C179.5 (11)
N1A—C9A—C10A—C10Ai−1.6 (2)C6C—C7C—C8C—C3C−1(3)
C1A—C9A—C10A—C10Ai178.32 (15)C9C—N1C—C8C—C7C179.2 (13)
C9B—C1B—C2B—C3B1.1 (5)C9C—N1C—C8C—C3C0.2 (19)
C1B—C2B—C3B—C8B1.6 (6)C2C—C3C—C8C—C7C−178.3 (17)
C1B—C2B—C3B—C4B−179.3 (4)C4C—C3C—C8C—C7C4(3)
C8B—C3B—C4B—C5B−0.5 (6)C2C—C3C—C8C—N1C1(2)
C2B—C3B—C4B—C5B−179.5 (4)C4C—C3C—C8C—N1C−176.8 (15)
C3B—C4B—C5B—C6B1.6 (6)C8C—N1C—C9C—C1C−2.0 (15)
C4B—C5B—C6B—C7B−1.5 (4)C8C—N1C—C9C—C10C177.9 (10)
C5B—C6B—C7B—C8B0.3 (4)C2C—C1C—C9C—N1C3.2 (16)
C9B—N1B—C8B—C3B1.1 (4)C2C—C1C—C9C—C10C−176.7 (11)
C9B—N1B—C8B—C7B179.8 (2)N1C—C9C—C10C—C10Cii−11.3 (12)
C4B—C3B—C8B—N1B178.1 (3)C1C—C9C—C10C—C10Cii168.6 (9)

Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2A—H2AA···Cg1iii0.932.773.3409 (14)121
C6A—H6AA···Cg2iv0.932.653.5328 (18)159
C4B—H4B···Cg3v0.932.853.376 (12)116
C6A—H6AA···Cg3vi0.932.763.613 (10)152

Symmetry codes: (iii) −x+1/2, y+1/2, −z+1/2; (iv) x−3/2, −y−1/2, z−1/2; (v) x−1/2, −y+1/2, z−1/2; (vi) −x+1/2, y−3/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2144).

References

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  • Goswami, S. P. & Mahapatra, A. K. (1998). Tetrahedron Lett.39, 1981–1984.
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