Literature DB >> 21583880

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

Makuteswaran Sridharan, Karnam J Rajendra Prasad, Matthias Zeller.   

Abstract

The title compound, C(26)H(19)ClN(2), is a 5,6-dihydro-13H-indolo[3,2-c]acridine prepared by condensation of a 2,3,4,9-n class="Species">tetra-hydro-1H-carbazol-1-one with 2-amino-benzophenone. 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 mol-ecule is inter-rupted by the saturated ethyl-ene 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⋯π inter-actions. No classical hydrogen bonds or stacking inter-actions are observed.

Entities:  

Year:  2009        PMID： 21583880      PMCID： PMC2977744          DOI： 10.1107/S1600536809013737

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

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

Experimental

Crystal data

C26H19ClN2 M = 394.88 Triclinic, a = 9.981 (4) Å b = 10.057 (4) Å c = 10.281 (4) Å α = 76.459 (7)° β = 80.279 (7)° γ = 81.754 (7)° V = 983.1 (7) Å3 Z = 2 Mo Kα radiation μ = 0.21 mm−1 T = 293 K 0.55 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.851, T max = 0.975 10234 measured reflections 4857 independent reflections 2826 reflections with I > 2σ(I) R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.053 wR(F 2) = 0.124 S = 1.02 4857 reflections 263 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.24 e Å−3 Data collection and cell refinement: APEX2 (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and Mercury (Macrae et al., 2008 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013737/fl2247sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013737/fl2247Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C26H19ClN2Z = 2
Mr = 394.88F(000) = 412
Triclinic, P1Dx = 1.334 Mg m−3
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 mm−1
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
Bruker SMART APEX CCD diffractometer4857 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 = −13→13
Tmin = 0.851, Tmax = 0.975k = −13→13
10234 measured reflectionsl = −13→13
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 = 1.02w = 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 Å−3
0 restraintsΔρmin = −0.24 e Å−3
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.
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*
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)
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—C12−178.5 (2)
C1—C2—C3—C4−0.2 (3)C13—C12—C17—N2175.20 (18)
C2—C3—C4—C5−0.3 (3)C11—C12—C17—N2−2.2 (2)
C2—C3—C4—Cl2179.24 (18)C13—C12—C17—C16−3.4 (3)
C3—C4—C5—C60.6 (3)C11—C12—C17—C16179.2 (2)
Cl2—C4—C5—C6−178.99 (15)C12—C11—C18—N2−2.4 (2)
N1—C1—C6—C5−179.55 (18)C10—C11—C18—N2−178.18 (18)
C2—C1—C6—C5−0.2 (3)C12—C11—C18—C19168.12 (19)
N1—C1—C6—C70.3 (3)C10—C11—C18—C19−7.7 (3)
C2—C1—C6—C7179.7 (2)C7—C8—C19—N10.0 (3)
C4—C5—C6—C1−0.3 (3)C9—C8—C19—N1−177.1 (2)
C4—C5—C6—C7179.8 (2)C7—C8—C19—C18−176.48 (18)
C1—C6—C7—C8−1.3 (3)C9—C8—C19—C186.4 (3)
C5—C6—C7—C8178.57 (19)C11—C18—C19—N1−159.1 (2)
C1—C6—C7—C21176.41 (18)N2—C18—C19—N110.0 (3)
C5—C6—C7—C21−3.7 (3)C11—C18—C19—C817.6 (3)
C6—C7—C8—C191.1 (3)N2—C18—C19—C8−173.25 (19)
C21—C7—C8—C19−176.52 (18)C8—C7—C21—C26−103.4 (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—C22−100.2 (2)
C19—C8—C9—C10−38.2 (3)C26—C21—C22—C23−0.3 (4)
C8—C9—C10—C1145.2 (3)C7—C21—C22—C23178.9 (2)
C9—C10—C11—C18−24.0 (3)C21—C22—C23—C240.0 (4)
C9—C10—C11—C12161.5 (2)C22—C23—C24—C250.5 (4)
C18—C11—C12—C13−174.0 (2)C23—C24—C25—C26−0.8 (4)
C10—C11—C12—C131.1 (4)C22—C21—C26—C250.0 (4)
C18—C11—C12—C172.8 (2)C7—C21—C26—C25−179.2 (2)
C10—C11—C12—C17177.9 (2)C24—C25—C26—C210.6 (4)
C17—C12—C13—C141.3 (3)C8—C19—N1—C1−1.0 (3)
C11—C12—C13—C14177.8 (2)C18—C19—N1—C1175.42 (17)
C12—C13—C14—C151.3 (4)C2—C1—N1—C19−178.57 (19)
C13—C14—C15—C16−2.1 (4)C6—C1—N1—C190.8 (3)
C14—C15—C16—C170.1 (4)C16—C17—N2—C18179.2 (2)
C14—C15—C16—C20−178.7 (2)C12—C17—N2—C180.8 (2)
C15—C16—C17—N2−175.6 (2)C11—C18—N2—C171.1 (2)
C20—C16—C17—N23.2 (4)C19—C18—N2—C17−169.34 (19)
D—H···AD—HH···AD···AD—H···A
C10—H10B···Cg1i0.972.963.848 (3)152
C26—H26···Cg2i0.932.513.391 (3)158
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the ring C1–C6 and Cg2 is the centroid of the indole ring.

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 code: (i) .

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