supplementary materials


Acta Cryst. (2009). E65, o1064    [ doi:10.1107/S1600536809013737 ]

9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine

M. Sridharan, K. J. Rajendra Prasad and M. Zeller

Abstract top

The title compound, C26H19ClN2, is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-tetrahydro-1H-carbazol-1-one with 2-aminobenzophenone. The crystals undergo a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on cooling rate and disturbance by vibration, thus indicating supercooling of the metastable room-temperature structure at lower temperature. The overall planarity of the indolo[3,2-c]acridine part of the molecule is interrupted by the saturated ethylene group, and the planes of the two halves exhibit a dihedral angle of 22.05 (6)° with each other while themselves being essentially planar. Packing is dominated by C-H...[pi] interactions. No classical hydrogen bonds or stacking interactions are observed.

Comment top

Nitrogen-containing heterocyclic compounds are the key building blocks used to develop compounds of biological and medicinal interest to chemists. Among nitrogen heterocycles, carbazole alkaloids represent an important class of natural products. The Indian medicinal plant Murraya koenigii spreng (Rutaceae) has been found to be a rich source of many carbazole alkaloids (Iyer & Devi, 2008). A number of carbazole alkaloids with intriguing novel structures and useful biological activities were isolated from natural sources over the past decades which had attracted chemists to frame novel synthetic strategies towards the synthesis of carbazole and its derivatives. The continuous increase of isolable natural products as well as pharmacological action of these carbazole derivatives has generated synthetic interest; consequently the syntheses of carbazoles have been a vigorously active area of study (Knölker & Reddy, 2002, and references therein; Choi et al. 2008).

Based on the structural, biological and pharmacological importance of the carbazole derivatives, the present investigation was aimed to devise a viable synthetic route to prepare these classes of compound using different synthetic methodologies. For our synthetic strategy 2,3,4,9-tetra-hydro-1H-carbazol-1-ones, prepared in our laboratory as potential precursors, have opened new avenues for the synthesis of highly functionalized carbazole derivatives. Based on these facts we have developed and reported an efficient syntheses of novel indoloacridines and have reported the crystallographic behavior of some of these compounds (Sridharan et al., 2009a,b). The current contribution presents the synthesis (Fig. 1) and crystal structure of the title compound which represents one such indoloacridine.

The compound undergoes a destructive phase change upon cooling at varying temperatures between 270 and 200 K, depending on cooling rate and disturbance by vibration, thus indicating supercooling of the room-temperature phase. To guarantee collection of a whole dataset the collection was thus performed at room temperture. An ORTEPstyle plot of the molecule is shown in Fig. 2.

The overall planarity of the indolo[3,2-c]acridine part of the molecule is interrupted by the saturated ethylene group of C9 and C10. The planes formed by C1 to C9, C19 and N1 as well as the plane made up of atoms C10 to C18, C20 and N2 are overall planar with r.m.s. deviations from planarity of only 0.01 and 0.03 Å, respectively. With each other the two planes form an angle of 22.05 (6)°. C10 deviates from the first plane by 0.807 (3) Å, C9 from the second by 0.476 (3) Å. The phenyl ring is at an angle to the first plane of 77.81 (6)°.

The N—H group does not form a classical hydrogen bond in the solid state and no strong ππ stacking interactions are observed. Other than van der Waals dispersive forces the packing of the compound in the solid state is dominated by C—H···π interactions (Fig. 3). The two most prominent such interactions are between C10—H10B and the centroid Cg1 of the ring built by atoms C1 to C6 (the chlorine-substituted phenyl ring), and between C26—H26 and the centroid Cg2 of the indole ring with H···Cg distances of 2.96 and 2.51 Å (Table 1). Additional very weak C—H···C and N—H···C interactions are indicated in Fig. 3.

In a recent publication (Sridharan et al., 2009b) we reported the structure of the dehydrogenated derivative of the title compound. It crystallizes in a primitive inversion symmetric setting with a similar volume as for the structure of the title compound. There are however no further reaching similarities between the structures of the two compounds. The hydrogenated molecule is essentially planar and packing, shape of the unit cell and location of the inversion centers are different for the two related compounds (Fig. 4).

Related literature top

For general background on the synthesis and properties of carbazole derivatives, see: Knölker & Reddy (2002); Choi et al. (2008). For synthesis and structures of indoloacridines, see: Sridharan et al. (2009a,b). For pharmacologically active ingredients (especially carbazole alkaloids) of Murraya koenigii spreng, see: Iyer & Devi (2008).

Experimental top

8-Methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.995 g, 5 mmol) and 2-amino-5-chlorobenzophenone (1.155 g, 5 mmol) were refluxed for 5 h in glacial acetic acid (4 ml) containing one drop of sulfuric acid. The reaction was monitored by TLC. After the completion of the reaction, the mixture was poured into crushed ice, extracted with chloroform, and the organic layer dried (Na2SO4). The crude product obtained on removal of the solvent was purified by column chromatography over silica gel using petroleum ether:ethyl acetate (98:5) to yield the title compound. 1.26 g, 64%, m.p. 527–529 K. Single crystals suitable for data collection were grown by slow evaporation from a solution in ethanol.

Refinement top

All H atoms were added in calculated positions with C—H bond distances of 0.97 (methylene), 0.93 (aromatic) and 0.96 Å (methyl) and an N—H distance of 0.86 Å. They were refined with isotropic displacement parameters Uiso of 1.5 (methyl) or 1.2 times Ueq (all others) of the adjacent C or N atom.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: APEX2 (Bruker, 2008); 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 Mercury (Macrae et al., 2008).

Figures top
[Figure 1] Fig. 1. Synthesis of the title compound
[Figure 2] Fig. 2. Thermal ellipsoid plot of the title compound with the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level, H atoms are shown as capped sticks.
[Figure 3] Fig. 3. Packing view of the title compound showing C—H···π interactions and very weak C—H···C and N—H···C interactions (blue dotted lines).
[Figure 4] Fig. 4. Overlay of the title compound with its hydrogenated counterpart (Sridharan et al., 2009b). The chlorobenzene part of the top molecule was used to define the overlay of the two compounds. The other molecules are created by the symmetry operations of their respective structures.
9-Chloro-1-methyl-7-phenyl-5,6-dihydro-13H-indolo[3,2-c]acridine top
Crystal data top
C26H19ClN2Z = 2
Mr = 394.88F(000) = 412
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.981 (4) ÅCell parameters from 417 reflections
b = 10.057 (4) Åθ = 2.6–30.3°
c = 10.281 (4) ŵ = 0.21 mm1
α = 76.459 (7)°T = 293 K
β = 80.279 (7)°Needle, yellow
γ = 81.754 (7)°0.55 × 0.20 × 0.12 mm
V = 983.1 (7) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer
4857 independent reflections
Radiation source: fine-focus sealed tube2826 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scansθmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan
(APEX2; Bruker, 2008)
h = 1313
Tmin = 0.851, Tmax = 0.975k = 1313
10234 measured reflectionsl = 1313
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0406P)2 + 0.0904P]
where P = (Fo2 + 2Fc2)/3
4857 reflections(Δ/σ)max = 0.001
263 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C26H19ClN2γ = 81.754 (7)°
Mr = 394.88V = 983.1 (7) Å3
Triclinic, P1Z = 2
a = 9.981 (4) ÅMo Kα radiation
b = 10.057 (4) ŵ = 0.21 mm1
c = 10.281 (4) ÅT = 293 K
α = 76.459 (7)°0.55 × 0.20 × 0.12 mm
β = 80.279 (7)°
Data collection top
Bruker SMART APEX CCD
diffractometer
4857 independent reflections
Absorption correction: multi-scan
(APEX2; Bruker, 2008)
2826 reflections with I > 2σ(I)
Tmin = 0.851, Tmax = 0.975Rint = 0.038
10234 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.053H-atom parameters constrained
wR(F2) = 0.124Δρmax = 0.17 e Å3
S = 1.02Δρmin = 0.24 e Å3
4857 reflectionsAbsolute structure: ?
263 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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
C11.0539 (2)0.6878 (2)0.9185 (2)0.0377 (5)
C21.1590 (2)0.6123 (2)0.8474 (2)0.0483 (6)
H21.16280.62310.75460.058*
C31.2550 (2)0.5237 (2)0.9125 (2)0.0499 (6)
H31.32370.47410.86450.060*
C41.2495 (2)0.5079 (2)1.0516 (2)0.0433 (5)
C51.1507 (2)0.5793 (2)1.1249 (2)0.0401 (5)
H51.14980.56741.21750.048*
C61.04930 (19)0.6717 (2)1.05958 (19)0.0360 (5)
C70.9424 (2)0.7498 (2)1.12968 (19)0.0366 (5)
C80.8504 (2)0.8392 (2)1.0570 (2)0.0384 (5)
C90.7306 (2)0.9240 (2)1.1197 (2)0.0481 (6)
H9A0.75040.93491.20560.058*
H9B0.65090.87411.13790.058*
C100.6961 (2)1.0667 (2)1.0325 (2)0.0481 (6)
H10A0.60641.10581.06750.058*
H10B0.76251.12701.03570.058*
C110.6973 (2)1.0559 (2)0.8900 (2)0.0399 (5)
C120.6403 (2)1.1467 (2)0.7787 (2)0.0406 (5)
C130.5656 (2)1.2770 (2)0.7608 (2)0.0509 (6)
H130.54051.32160.83230.061*
C140.5304 (2)1.3371 (3)0.6356 (3)0.0607 (7)
H140.48251.42450.62190.073*
C150.5649 (2)1.2703 (3)0.5283 (3)0.0606 (7)
H150.53641.31350.44570.073*
C160.6396 (2)1.1428 (2)0.5396 (2)0.0496 (6)
C170.6786 (2)1.0840 (2)0.6669 (2)0.0412 (5)
C180.7711 (2)0.9486 (2)0.8411 (2)0.0388 (5)
C190.8654 (2)0.8472 (2)0.91467 (19)0.0370 (5)
C200.6795 (3)1.0715 (3)0.4238 (2)0.0692 (8)
H20A0.63581.12260.34820.104*
H20B0.65120.98050.45030.104*
H20C0.77691.06570.39870.104*
C210.9294 (2)0.7292 (2)1.27990 (19)0.0373 (5)
C220.8344 (2)0.6490 (3)1.3624 (2)0.0557 (6)
H220.77730.60891.32360.067*
C230.8222 (3)0.6269 (3)1.5009 (2)0.0594 (7)
H230.75740.57231.55480.071*
C240.9056 (2)0.6854 (2)1.5591 (2)0.0493 (6)
H240.89830.67031.65270.059*
C250.9988 (3)0.7656 (3)1.4794 (2)0.0608 (7)
H251.05480.80651.51880.073*
C261.0116 (2)0.7874 (3)1.3397 (2)0.0575 (7)
H261.07670.84201.28640.069*
Cl21.37259 (6)0.39220 (7)1.13247 (6)0.0601 (2)
N10.96084 (17)0.77544 (17)0.84684 (16)0.0407 (4)
N20.75957 (17)0.96338 (17)0.70665 (17)0.0433 (4)
H2A0.79660.90690.65630.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0383 (11)0.0386 (12)0.0376 (11)0.0026 (9)0.0047 (9)0.0122 (9)
C20.0522 (13)0.0554 (15)0.0375 (12)0.0053 (11)0.0065 (10)0.0170 (11)
C30.0457 (13)0.0552 (15)0.0493 (13)0.0090 (11)0.0070 (10)0.0208 (12)
C40.0414 (12)0.0400 (12)0.0476 (13)0.0002 (10)0.0110 (10)0.0069 (10)
C50.0420 (12)0.0422 (13)0.0352 (11)0.0035 (10)0.0069 (9)0.0059 (10)
C60.0382 (11)0.0361 (11)0.0348 (11)0.0046 (9)0.0044 (9)0.0098 (9)
C70.0406 (11)0.0359 (12)0.0335 (10)0.0060 (9)0.0032 (9)0.0084 (9)
C80.0400 (11)0.0383 (12)0.0363 (11)0.0038 (9)0.0015 (9)0.0098 (9)
C90.0495 (13)0.0506 (14)0.0398 (12)0.0051 (11)0.0006 (10)0.0109 (11)
C100.0538 (14)0.0446 (14)0.0448 (13)0.0035 (11)0.0038 (10)0.0147 (11)
C110.0397 (11)0.0359 (12)0.0427 (12)0.0005 (9)0.0038 (9)0.0094 (10)
C120.0360 (11)0.0391 (12)0.0455 (12)0.0003 (10)0.0040 (9)0.0105 (10)
C130.0504 (14)0.0418 (13)0.0583 (15)0.0047 (11)0.0051 (11)0.0139 (12)
C140.0621 (16)0.0425 (14)0.0703 (17)0.0089 (12)0.0152 (13)0.0026 (13)
C150.0665 (16)0.0538 (16)0.0576 (15)0.0043 (13)0.0236 (13)0.0002 (13)
C160.0544 (14)0.0459 (14)0.0491 (14)0.0024 (11)0.0170 (11)0.0064 (11)
C170.0403 (12)0.0358 (12)0.0474 (13)0.0007 (10)0.0109 (9)0.0076 (10)
C180.0438 (12)0.0377 (12)0.0352 (11)0.0016 (10)0.0073 (9)0.0090 (9)
C190.0402 (11)0.0356 (12)0.0361 (11)0.0023 (9)0.0048 (9)0.0106 (9)
C200.090 (2)0.0684 (18)0.0523 (15)0.0027 (15)0.0249 (14)0.0146 (14)
C210.0389 (11)0.0392 (12)0.0330 (11)0.0012 (10)0.0040 (9)0.0089 (9)
C220.0668 (16)0.0670 (17)0.0387 (13)0.0280 (14)0.0050 (11)0.0115 (12)
C230.0729 (17)0.0674 (17)0.0386 (13)0.0267 (14)0.0006 (12)0.0069 (12)
C240.0595 (15)0.0525 (14)0.0338 (11)0.0004 (12)0.0067 (10)0.0087 (11)
C250.0627 (16)0.0808 (19)0.0467 (14)0.0232 (15)0.0142 (12)0.0151 (13)
C260.0587 (15)0.0747 (18)0.0430 (13)0.0280 (14)0.0049 (11)0.0096 (13)
Cl20.0529 (4)0.0598 (4)0.0614 (4)0.0131 (3)0.0138 (3)0.0083 (3)
N10.0444 (10)0.0417 (10)0.0368 (9)0.0045 (8)0.0088 (8)0.0134 (8)
N20.0524 (11)0.0383 (10)0.0408 (10)0.0047 (9)0.0107 (8)0.0148 (8)
Geometric parameters (Å, °) top
C1—N11.369 (2)C13—H130.9300
C1—C21.408 (3)C14—C151.393 (3)
C1—C61.415 (3)C14—H140.9300
C2—C31.361 (3)C15—C161.378 (3)
C2—H20.9300C15—H150.9300
C3—C41.394 (3)C16—C171.400 (3)
C3—H30.9300C16—C201.499 (3)
C4—C51.362 (3)C17—N21.375 (2)
C4—Cl21.742 (2)C18—N21.378 (2)
C5—C61.416 (3)C18—C191.450 (3)
C5—H50.9300C19—N11.315 (2)
C6—C71.428 (3)C20—H20A0.9600
C7—C81.375 (3)C20—H20B0.9600
C7—C211.495 (3)C20—H20C0.9600
C8—C191.430 (3)C21—C261.368 (3)
C8—C91.509 (3)C21—C221.377 (3)
C9—C101.530 (3)C22—C231.375 (3)
C9—H9A0.9700C22—H220.9300
C9—H9B0.9700C23—C241.368 (3)
C10—C111.492 (3)C23—H230.9300
C10—H10A0.9700C24—C251.355 (3)
C10—H10B0.9700C24—H240.9300
C11—C181.364 (3)C25—C261.388 (3)
C11—C121.432 (3)C25—H250.9300
C12—C131.400 (3)C26—H260.9300
C12—C171.410 (3)N2—H2A0.8600
C13—C141.369 (3)
N1—C1—C2118.08 (18)C13—C14—H14119.3
N1—C1—C6122.72 (18)C15—C14—H14119.3
C2—C1—C6119.20 (18)C16—C15—C14122.7 (2)
C3—C2—C1121.0 (2)C16—C15—H15118.6
C3—C2—H2119.5C14—C15—H15118.6
C1—C2—H2119.5C15—C16—C17115.4 (2)
C2—C3—C4119.4 (2)C15—C16—C20123.0 (2)
C2—C3—H3120.3C17—C16—C20121.6 (2)
C4—C3—H3120.3N2—C17—C16128.9 (2)
C5—C4—C3121.83 (19)N2—C17—C12108.05 (17)
C5—C4—Cl2119.76 (16)C16—C17—C12123.0 (2)
C3—C4—Cl2118.41 (16)C11—C18—N2110.36 (18)
C4—C5—C6119.80 (18)C11—C18—C19123.91 (18)
C4—C5—H5120.1N2—C18—C19124.99 (18)
C6—C5—H5120.1N1—C19—C8125.10 (18)
C1—C6—C5118.68 (18)N1—C19—C18118.81 (18)
C1—C6—C7118.34 (18)C8—C19—C18116.00 (18)
C5—C6—C7122.98 (18)C16—C20—H20A109.5
C8—C7—C6118.72 (17)C16—C20—H20B109.5
C8—C7—C21121.44 (18)H20A—C20—H20B109.5
C6—C7—C21119.80 (17)C16—C20—H20C109.5
C7—C8—C19118.02 (18)H20A—C20—H20C109.5
C7—C8—C9123.77 (18)H20B—C20—H20C109.5
C19—C8—C9118.14 (18)C26—C21—C22117.98 (19)
C8—C9—C10114.34 (18)C26—C21—C7121.54 (19)
C8—C9—H9A108.7C22—C21—C7120.48 (18)
C10—C9—H9A108.7C23—C22—C21121.5 (2)
C8—C9—H9B108.7C23—C22—H22119.3
C10—C9—H9B108.7C21—C22—H22119.3
H9A—C9—H9B107.6C24—C23—C22119.8 (2)
C11—C10—C9109.85 (18)C24—C23—H23120.1
C11—C10—H10A109.7C22—C23—H23120.1
C9—C10—H10A109.7C25—C24—C23119.5 (2)
C11—C10—H10B109.7C25—C24—H24120.3
C9—C10—H10B109.7C23—C24—H24120.3
H10A—C10—H10B108.2C24—C25—C26120.7 (2)
C18—C11—C12106.56 (18)C24—C25—H25119.6
C18—C11—C10121.04 (18)C26—C25—H25119.6
C12—C11—C10132.23 (19)C21—C26—C25120.5 (2)
C13—C12—C17118.90 (19)C21—C26—H26119.7
C13—C12—C11134.2 (2)C25—C26—H26119.7
C17—C12—C11106.81 (18)C19—N1—C1117.09 (17)
C14—C13—C12118.4 (2)C17—N2—C18108.15 (17)
C14—C13—H13120.8C17—N2—H2A125.9
C12—C13—H13120.8C18—N2—H2A125.9
C13—C14—C15121.4 (2)
N1—C1—C2—C3179.8 (2)C15—C16—C17—C122.6 (3)
C6—C1—C2—C30.5 (3)C20—C16—C17—C12178.5 (2)
C1—C2—C3—C40.2 (3)C13—C12—C17—N2175.20 (18)
C2—C3—C4—C50.3 (3)C11—C12—C17—N22.2 (2)
C2—C3—C4—Cl2179.24 (18)C13—C12—C17—C163.4 (3)
C3—C4—C5—C60.6 (3)C11—C12—C17—C16179.2 (2)
Cl2—C4—C5—C6178.99 (15)C12—C11—C18—N22.4 (2)
N1—C1—C6—C5179.55 (18)C10—C11—C18—N2178.18 (18)
C2—C1—C6—C50.2 (3)C12—C11—C18—C19168.12 (19)
N1—C1—C6—C70.3 (3)C10—C11—C18—C197.7 (3)
C2—C1—C6—C7179.7 (2)C7—C8—C19—N10.0 (3)
C4—C5—C6—C10.3 (3)C9—C8—C19—N1177.1 (2)
C4—C5—C6—C7179.8 (2)C7—C8—C19—C18176.48 (18)
C1—C6—C7—C81.3 (3)C9—C8—C19—C186.4 (3)
C5—C6—C7—C8178.57 (19)C11—C18—C19—N1159.1 (2)
C1—C6—C7—C21176.41 (18)N2—C18—C19—N110.0 (3)
C5—C6—C7—C213.7 (3)C11—C18—C19—C817.6 (3)
C6—C7—C8—C191.1 (3)N2—C18—C19—C8173.25 (19)
C21—C7—C8—C19176.52 (18)C8—C7—C21—C26103.4 (3)
C6—C7—C8—C9178.06 (19)C6—C7—C21—C2678.9 (3)
C21—C7—C8—C90.4 (3)C8—C7—C21—C2277.4 (3)
C7—C8—C9—C10144.9 (2)C6—C7—C21—C22100.2 (2)
C19—C8—C9—C1038.2 (3)C26—C21—C22—C230.3 (4)
C8—C9—C10—C1145.2 (3)C7—C21—C22—C23178.9 (2)
C9—C10—C11—C1824.0 (3)C21—C22—C23—C240.0 (4)
C9—C10—C11—C12161.5 (2)C22—C23—C24—C250.5 (4)
C18—C11—C12—C13174.0 (2)C23—C24—C25—C260.8 (4)
C10—C11—C12—C131.1 (4)C22—C21—C26—C250.0 (4)
C18—C11—C12—C172.8 (2)C7—C21—C26—C25179.2 (2)
C10—C11—C12—C17177.9 (2)C24—C25—C26—C210.6 (4)
C17—C12—C13—C141.3 (3)C8—C19—N1—C11.0 (3)
C11—C12—C13—C14177.8 (2)C18—C19—N1—C1175.42 (17)
C12—C13—C14—C151.3 (4)C2—C1—N1—C19178.57 (19)
C13—C14—C15—C162.1 (4)C6—C1—N1—C190.8 (3)
C14—C15—C16—C170.1 (4)C16—C17—N2—C18179.2 (2)
C14—C15—C16—C20178.7 (2)C12—C17—N2—C180.8 (2)
C15—C16—C17—N2175.6 (2)C11—C18—N2—C171.1 (2)
C20—C16—C17—N23.2 (4)C19—C18—N2—C17169.34 (19)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···Cg1i0.972.963.848 (3)152
C26—H26···Cg2i0.932.513.391 (3)158
Symmetry codes: (i) −x+2, −y+2, −z+2.
Table 1
Hydrogen-bond geometry (Å, °)
top
D—H···AD—HH···AD···AD—H···A
C10—H10B···Cg1i0.972.963.848 (3)152
C26—H26···Cg2i0.932.513.391 (3)158
Symmetry codes: (i) −x+2, −y+2, −z+2.
Acknowledgements top

The authors acknowledge the UGC, New Delhi, India, for the award of a Major Research Project (grant No. F.31-122/2005). MS thanks the UGC, New Delhi, for the award of a research fellowship. The diffractometer was funded by NSF grant No. 0087210, by Ohio Board of Regents grant No. CAP-491, and by YSU.

references
References top

Bruker (2008). APEX2. Bruker AXS Inc, Madison, Wisconsin, USA.

Choi, T., Czerwonka, R., Forke, R., Jäger, A., Knöll, J., Krahl, M. P., Krause, T., Reddy, K. R., Franzblau, S. G. & Knölker, H.-J. (2008). Med. Chem. Res. 17, 374–385.

Iyer, D. & Devi, P. U. (2008). Pharmacogn. Rev. 2, 180–184.

Knölker, H. J. & Reddy, K. R. (2002). Chem. Rev. 102, 4303–4427.

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Sridharan, M., Rajendra Prasad, K. J., Kotheimer, A. E., Wagner, T. R. & Zeller, M. (2009b). J. Chem. Crystallogr. 39. In the press. [Any update? DOI?]

Sridharan, M., Rajendra Prasad, K. J., Ngendahimana, A. & Zeller, M. (2009a). J. Chem. Crystallogr. 39, 270–278.