Literature DB >> 21588408

1,1'-(9-Octyl-9H-carbazole-3,6-di-yl)diethanone.

Aamer Saeed, Madiha Kazmi, Shahid Ameen Samra, Madiha Irfan, Michael Bolte.   

Abstract

The central structural element of the title compound, C(24)H(29)NO(2), is a carbazole unit substituted with two acetyl residues and an octyl chain. The acetyl residues are nearly coplanar [dihedral angles = 5.37 (14) and 1.0 (3)°] with the carbazole unit which is essentially planar (r.m.s. deviation for all non-H atoms = 0.025 Å). The octyl chain adopts an all-trans conformation. The crystal packing is stabilized by C-H⋯O hydrogen bonds.

Entities:  

Year:  2010        PMID： 21588408      PMCID： PMC3007423          DOI： 10.1107/S1600536810028928

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


Related literature

For details of the biological activity of carbazoles, see: Yamashita et al. (1992 ▶). For properties of aromatic carbazolyl groups, see: Law (1992 ▶). For the properties and applications of carbazole-containing polymers, see: Strohriegl & Grazulevicius (1997 ▶).

Experimental

Crystal data

C24H29NO2 M = 363.48 Orthorhombic, a = 18.746 (2) Å b = 10.3842 (18) Å c = 20.994 (3) Å V = 4086.7 (10) Å3 Z = 8 Mo Kα radiation μ = 0.07 mm−1 T = 173 K 0.32 × 0.29 × 0.12 mm

Data collection

Stow IPDS II diffractometer 8614 measured reflections 3613 independent reflections 2024 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.086 S = 0.85 3613 reflections 248 parameters H-atom parameters constrained Δρmax = 0.20 e Å−3 Δρmin = −0.20 e Å−3 Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028928/bv2151sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028928/bv2151Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C24H29NO2F(000) = 1568
Mr = 363.48Dx = 1.182 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3794 reflections
a = 18.746 (2) Åθ = 3.6–25.9°
b = 10.3842 (18) ŵ = 0.07 mm−1
c = 20.994 (3) ÅT = 173 K
V = 4086.7 (10) Å3Plate, colourless
Z = 80.32 × 0.29 × 0.12 mm
Stow IPDS II two-circle diffractometer2024 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.031
graphiteθmax = 25.0°, θmin = 1.9°
ω scansh = 0→22
8614 measured reflectionsk = 0→12
3613 independent reflectionsl = 0→24
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.086w = 1/[σ2(Fo2) + (0.0389P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max = 0.001
3613 reflectionsΔρmax = 0.20 e Å−3
248 parametersΔρmin = −0.20 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0019 (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
N10.70663 (9)0.23596 (8)0.66696 (8)0.0259 (4)
O10.68112 (9)0.13339 (7)0.37076 (7)0.0482 (4)
O20.45645 (10)0.58614 (10)0.56767 (8)0.0579 (5)
C10.75428 (11)0.21735 (9)0.72139 (9)0.0300 (5)
H1A0.77870.13320.71700.036*
H1B0.72550.21470.76090.036*
C20.81004 (11)0.32270 (10)0.72736 (9)0.0340 (5)
H2A0.84160.30230.76380.041*
H2B0.78560.40500.73700.041*
C30.85589 (12)0.34086 (10)0.66809 (10)0.0335 (5)
H3A0.82470.36400.63180.040*
H3B0.87970.25840.65770.040*
C40.91269 (11)0.44553 (10)0.67644 (10)0.0342 (5)
H4A0.88920.52590.69070.041*
H4B0.94630.41860.71030.041*
C50.95472 (12)0.47302 (9)0.61566 (10)0.0358 (5)
H5A0.97700.39210.60070.043*
H5B0.92130.50240.58220.043*
C61.01263 (12)0.57443 (10)0.62449 (10)0.0376 (5)
H6A1.04990.53960.65310.045*
H6B0.99160.65090.64550.045*
C71.04725 (13)0.61615 (10)0.56216 (12)0.0472 (6)
H7A1.00980.64870.53310.057*
H7B1.06950.54020.54180.057*
C81.10405 (14)0.72094 (10)0.57099 (14)0.0696 (9)
H8A1.08120.80060.58550.104*
H8B1.12820.73660.53030.104*
H8C1.13900.69260.60280.104*
C110.71650 (11)0.18471 (9)0.60607 (9)0.0251 (4)
C120.66565 (10)0.23960 (8)0.56417 (9)0.0217 (4)
C130.66665 (11)0.20425 (9)0.49974 (9)0.0249 (4)
H130.63340.24060.47070.030*
C140.71716 (11)0.11499 (9)0.47877 (10)0.0260 (4)
C150.76638 (11)0.06208 (9)0.52180 (10)0.0295 (5)
H150.80030.00130.50680.035*
C160.76684 (11)0.09608 (9)0.58571 (9)0.0290 (5)
H160.80040.05990.61450.035*
C170.72007 (12)0.08031 (9)0.40940 (10)0.0310 (5)
C180.77287 (12)−0.01784 (9)0.38732 (9)0.0405 (6)
H18A0.7674−0.03140.34140.061*
H18B0.7646−0.09920.40980.061*
H18C0.82130.01270.39630.061*
C210.65132 (10)0.32388 (11)0.66472 (9)0.0240 (4)
C220.62341 (11)0.32930 (10)0.60171 (9)0.0234 (4)
C230.56768 (10)0.41338 (8)0.58793 (9)0.0249 (4)
H230.54860.41820.54610.030*
C240.54038 (10)0.49026 (10)0.63647 (9)0.0249 (4)
C250.56898 (11)0.48308 (11)0.69854 (9)0.0264 (4)
H250.54950.53640.73090.032*
C260.62438 (11)0.40090 (8)0.71366 (9)0.0262 (4)
H260.64340.39690.75560.031*
C270.48115 (12)0.58090 (11)0.62149 (10)0.0320 (5)
C280.44961 (11)0.66343 (9)0.67328 (10)0.0367 (5)
H28A0.41680.72630.65440.055*
H28B0.48790.70880.69570.055*
H28C0.42350.60890.70340.055*
U11U22U33U12U13U23
N10.0267 (9)0.0301 (4)0.0209 (9)0.0028 (7)−0.0033 (8)0.0032 (7)
O10.0590 (11)0.0599 (4)0.0255 (9)0.0280 (8)−0.0093 (9)−0.0055 (6)
O20.0641 (12)0.0820 (6)0.0276 (9)0.0404 (9)−0.0134 (9)−0.0098 (9)
C10.0336 (12)0.0367 (4)0.0198 (11)0.0043 (9)−0.0051 (11)0.0048 (8)
C20.0343 (13)0.0419 (4)0.0258 (12)0.0033 (10)−0.0061 (10)−0.0030 (9)
C30.0323 (11)0.0375 (4)0.0306 (12)0.0017 (9)−0.0050 (11)−0.0043 (9)
C40.0329 (11)0.0383 (5)0.0315 (13)0.0030 (9)−0.0040 (11)−0.0048 (9)
C50.0390 (13)0.0353 (4)0.0330 (13)0.0008 (9)−0.0035 (11)0.0015 (7)
C60.0354 (12)0.0404 (4)0.0372 (13)0.0002 (10)−0.0037 (11)−0.0020 (8)
C70.0437 (15)0.0484 (5)0.0494 (16)−0.0020 (10)0.0038 (13)0.0011 (10)
C80.0539 (19)0.0634 (6)0.092 (2)−0.0126 (11)0.0141 (18)0.0065 (11)
C110.0276 (11)0.0257 (4)0.0219 (11)−0.0021 (9)0.0010 (10)0.0025 (8)
C120.0219 (10)0.0199 (4)0.0233 (11)−0.0022 (8)−0.0003 (9)0.0009 (7)
C130.0269 (10)0.0267 (4)0.0211 (11)0.0002 (8)−0.0018 (10)0.0013 (7)
C140.0292 (10)0.0264 (4)0.0224 (11)0.0011 (8)−0.0007 (10)−0.0010 (8)
C150.0316 (12)0.0272 (4)0.0298 (12)0.0070 (8)−0.0010 (10)−0.0001 (8)
C160.0315 (13)0.0287 (4)0.0268 (11)0.0059 (9)−0.0055 (10)0.0016 (8)
C170.0344 (12)0.0304 (4)0.0281 (12)0.0030 (9)−0.0002 (11)−0.0031 (8)
C180.0476 (15)0.0435 (5)0.0303 (13)0.0130 (10)−0.0009 (11)−0.0073 (7)
C210.0238 (10)0.0266 (4)0.0217 (11)−0.0039 (8)0.0013 (9)0.0037 (8)
C220.0228 (10)0.0275 (4)0.0200 (10)−0.0014 (9)0.0015 (9)0.0026 (8)
C230.0252 (10)0.0293 (4)0.0202 (10)0.0004 (8)−0.0014 (9)0.0009 (7)
C240.0243 (10)0.0305 (5)0.0200 (11)0.0034 (9)0.0012 (10)0.0012 (8)
C250.0273 (10)0.0315 (4)0.0204 (11)0.0002 (9)0.0038 (9)−0.0006 (8)
C260.0281 (11)0.0324 (4)0.0180 (10)−0.0020 (8)0.0014 (10)0.0013 (7)
C270.0325 (13)0.0384 (5)0.0251 (12)0.0054 (10)0.0012 (10)0.0012 (9)
C280.0377 (14)0.0439 (4)0.0285 (12)0.0140 (9)0.0032 (11)−0.0022 (8)
N1—C211.382 (2)C11—C161.386 (2)
N1—C111.397 (2)C11—C121.417 (2)
N1—C11.463 (2)C12—C131.402 (2)
O1—C171.223 (2)C12—C221.455 (2)
O2—C271.222 (3)C13—C141.396 (2)
C1—C21.518 (2)C13—H130.9500
C1—H1A0.9900C14—C151.403 (3)
C1—H1B0.9900C14—C171.501 (3)
C2—C31.524 (3)C15—C161.388 (3)
C2—H2A0.9900C15—H150.9500
C2—H2B0.9900C16—H160.9500
C3—C41.532 (2)C17—C181.494 (2)
C3—H3A0.9900C18—H18A0.9800
C3—H3B0.9900C18—H18B0.9800
C4—C51.527 (3)C18—H18C0.9800
C4—H4A0.9900C21—C261.397 (2)
C4—H4B0.9900C21—C221.424 (3)
C5—C61.524 (2)C22—C231.392 (2)
C5—H5A0.9900C23—C241.392 (2)
C5—H5B0.9900C23—H230.9500
C6—C71.524 (3)C24—C251.411 (3)
C6—H6A0.9900C24—C271.489 (2)
C6—H6B0.9900C25—C261.381 (2)
C7—C81.534 (3)C25—H250.9500
C7—H7A0.9900C26—H260.9500
C7—H7B0.9900C27—C281.505 (3)
C8—H8A0.9800C28—H28A0.9800
C8—H8B0.9800C28—H28B0.9800
C8—H8C0.9800C28—H28C0.9800
C21—N1—C11108.65 (15)N1—C11—C12109.01 (13)
C21—N1—C1124.87 (15)C13—C12—C11119.00 (14)
C11—N1—C1125.69 (15)C13—C12—C22134.26 (16)
N1—C1—C2112.93 (12)C11—C12—C22106.70 (16)
N1—C1—H1A109.0C14—C13—C12119.16 (17)
C2—C1—H1A109.0C14—C13—H13120.4
N1—C1—H1B109.0C12—C13—H13120.4
C2—C1—H1B109.0C13—C14—C15120.19 (17)
H1A—C1—H1B107.8C13—C14—C17119.33 (17)
C1—C2—C3114.21 (15)C15—C14—C17120.44 (15)
C1—C2—H2A108.7C16—C15—C14121.80 (15)
C3—C2—H2A108.7C16—C15—H15119.1
C1—C2—H2B108.7C14—C15—H15119.1
C3—C2—H2B108.7C11—C16—C15117.59 (17)
H2A—C2—H2B107.6C11—C16—H16121.2
C2—C3—C4112.73 (16)C15—C16—H16121.2
C2—C3—H3A109.0O1—C17—C18119.81 (17)
C4—C3—H3A109.0O1—C17—C14120.92 (15)
C2—C3—H3B109.0C18—C17—C14119.25 (17)
C4—C3—H3B109.0C17—C18—H18A109.5
H3A—C3—H3B107.8C17—C18—H18B109.5
C5—C4—C3113.32 (16)H18A—C18—H18B109.5
C5—C4—H4A108.9C17—C18—H18C109.5
C3—C4—H4A108.9H18A—C18—H18C109.5
C5—C4—H4B108.9H18B—C18—H18C109.5
C3—C4—H4B108.9N1—C21—C26128.64 (17)
H4A—C4—H4B107.7N1—C21—C22109.47 (16)
C6—C5—C4113.28 (17)C26—C21—C22121.87 (16)
C6—C5—H5A108.9C23—C22—C21119.59 (16)
C4—C5—H5A108.9C23—C22—C12134.23 (17)
C6—C5—H5B108.9C21—C22—C12106.15 (15)
C4—C5—H5B108.9C24—C23—C22118.92 (17)
H5A—C5—H5B107.7C24—C23—H23120.5
C5—C6—C7113.29 (18)C22—C23—H23120.5
C5—C6—H6A108.9C23—C24—C25120.40 (16)
C7—C6—H6A108.9C23—C24—C27118.81 (17)
C5—C6—H6B108.9C25—C24—C27120.78 (17)
C7—C6—H6B108.9C26—C25—C24122.04 (16)
H6A—C6—H6B107.7C26—C25—H25119.0
C6—C7—C8113.2 (2)C24—C25—H25119.0
C6—C7—H7A108.9C25—C26—C21117.18 (17)
C8—C7—H7A108.9C25—C26—H26121.4
C6—C7—H7B108.9C21—C26—H26121.4
C8—C7—H7B108.9O2—C27—C24120.39 (18)
H7A—C7—H7B107.8O2—C27—C28119.58 (18)
C7—C8—H8A109.5C24—C27—C28120.00 (18)
C7—C8—H8B109.5C27—C28—H28A109.5
H8A—C8—H8B109.5C27—C28—H28B109.5
C7—C8—H8C109.5H28A—C28—H28B109.5
H8A—C8—H8C109.5C27—C28—H28C109.5
H8B—C8—H8C109.5H28A—C28—H28C109.5
C16—C11—N1128.72 (17)H28B—C28—H28C109.5
C16—C11—C12122.26 (16)
C21—N1—C1—C2−76.3 (2)C13—C14—C17—C18−178.38 (14)
C11—N1—C1—C292.42 (16)C15—C14—C17—C184.0 (2)
N1—C1—C2—C3−56.0 (2)C11—N1—C21—C26−177.94 (14)
C1—C2—C3—C4−178.57 (13)C1—N1—C21—C26−7.6 (2)
C2—C3—C4—C5−174.96 (14)C11—N1—C21—C220.98 (17)
C3—C4—C5—C6−178.36 (13)C1—N1—C21—C22171.30 (15)
C4—C5—C6—C7−171.59 (14)N1—C21—C22—C23−179.02 (12)
C5—C6—C7—C8178.39 (15)C26—C21—C22—C230.0 (2)
C21—N1—C11—C16178.24 (14)N1—C21—C22—C12−0.66 (17)
C1—N1—C11—C168.0 (2)C26—C21—C22—C12178.35 (13)
C21—N1—C11—C12−0.92 (16)C13—C12—C22—C230.5 (3)
C1—N1—C11—C12−171.13 (13)C11—C12—C22—C23178.11 (17)
C16—C11—C12—C13−0.7 (2)C13—C12—C22—C21−177.50 (17)
N1—C11—C12—C13178.53 (14)C11—C12—C22—C210.10 (16)
C16—C11—C12—C22−178.73 (13)C21—C22—C23—C24−0.2 (2)
N1—C11—C12—C220.49 (16)C12—C22—C23—C24−177.96 (16)
C11—C12—C13—C140.7 (2)C22—C23—C24—C250.2 (2)
C22—C12—C13—C14178.06 (14)C22—C23—C24—C27179.51 (15)
C12—C13—C14—C15−0.3 (2)C23—C24—C25—C260.0 (2)
C12—C13—C14—C17−177.90 (14)C27—C24—C25—C26−179.33 (13)
C13—C14—C15—C16−0.2 (2)C24—C25—C26—C21−0.2 (2)
C17—C14—C15—C16177.43 (16)N1—C21—C26—C25178.98 (14)
N1—C11—C16—C15−178.79 (15)C22—C21—C26—C250.2 (2)
C12—C11—C16—C150.3 (2)C23—C24—C27—O21.0 (3)
C14—C15—C16—C110.2 (2)C25—C24—C27—O2−179.67 (18)
C13—C14—C17—O13.4 (2)C23—C24—C27—C28178.84 (14)
C15—C14—C17—O1−174.24 (15)C25—C24—C27—C28−1.8 (2)
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.952.593.474 (2)154
C23—H23···O2i0.952.393.298 (3)160
C28—H28A···O1i0.982.403.363 (2)166
C26—H26···O1ii0.952.543.484 (2)173
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C13—H13⋯O2i0.952.593.474 (2)154
C23—H23⋯O2i0.952.393.298 (3)160
C28—H28A⋯O1i0.982.403.363 (2)166
C26—H26⋯O1ii0.952.543.484 (2)173

Symmetry codes: (i) ; (ii) .

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