Literature DB >> 21582438

4-Methyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

M Sridharan, K J Rajendra Prasad, A Thomas Gunaseelan, A Thiruvalluvar, R J Butcher.   

Abstract

In the title compound, C(14)H(15)NO, the seven-membered ring exhibits a slightly distorted twist-boat conformation. The pyrrole ring forms a dihedral angle of 1.44 (10)° with the fused benzene ring. N-H⋯O hydrogen bonds form a centrosymmetric dimer and weak C-H⋯π inter-actions are also found in the crystal structure.

Entities:  

Year:  2009        PMID： 21582438      PMCID： PMC2968932          DOI： 10.1107/S1600536809007429

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


Related literature

For a related crystal structure, see: Sridharan et al. (2008 ▶).

Experimental

Crystal data

C14H15NO M = 213.27 Monoclinic, a = 9.6731 (4) Å b = 10.0924 (5) Å c = 11.8328 (6) Å β = 103.397 (5)° V = 1123.74 (10) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 295 K 0.55 × 0.45 × 0.26 mm

Data collection

Oxford Diffraction Gemini R diffractometer Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.936, T max = 1.000 (expected range = 0.917–0.980) 9586 measured reflections 3772 independent reflections 2044 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.077 wR(F 2) = 0.253 S = 1.04 3772 reflections 150 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.57 e Å−3 Δρmin = −0.30 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007429/wn2312sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007429/wn2312Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H15NOF(000) = 456
Mr = 213.27Dx = 1.261 Mg m−3
Monoclinic, P21/nMelting point: 412.5 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 9.6731 (4) ÅCell parameters from 3217 reflections
b = 10.0924 (5) Åθ = 4.7–32.7°
c = 11.8328 (6) ŵ = 0.08 mm−1
β = 103.397 (5)°T = 295 K
V = 1123.74 (10) Å3Prism, colourless
Z = 40.55 × 0.45 × 0.26 mm
Oxford Diffraction Gemini R diffractometer3772 independent reflections
Radiation source: fine-focus sealed tube2044 reflections with I > 2σ(I)
graphiteRint = 0.025
Detector resolution: 10.5081 pixels mm-1θmax = 32.8°, θmin = 4.7°
φ and ω scansh = −14→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −14→15
Tmin = 0.937, Tmax = 1.000l = −17→15
9586 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.253H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.1467P)2] where P = (Fo2 + 2Fc2)/3
3772 reflections(Δ/σ)max = 0.001
150 parametersΔρmax = 0.57 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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 > 2σ(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
O60.07595 (15)0.12098 (15)−0.05930 (13)0.0619 (5)
N50.23136 (16)−0.06788 (15)0.07124 (12)0.0407 (4)
C10.5759 (2)−0.1262 (3)0.25005 (19)0.0684 (9)
C20.5665 (3)−0.2535 (3)0.2849 (2)0.0765 (9)
C30.4432 (3)−0.3286 (3)0.24770 (18)0.0677 (9)
C40.3234 (2)−0.2780 (2)0.17452 (17)0.0523 (7)
C4A0.33242 (19)−0.14568 (19)0.14131 (14)0.0430 (5)
C5A0.28716 (17)0.05736 (17)0.06406 (14)0.0398 (5)
C60.19212 (19)0.15599 (19)−0.00273 (15)0.0445 (6)
C70.2291 (3)0.3012 (2)0.0012 (2)0.0648 (8)
C80.3799 (3)0.3459 (3)0.0216 (3)0.0855 (11)
C90.4803 (3)0.3090 (3)0.1286 (3)0.0892 (11)
C100.5353 (2)0.1680 (3)0.1405 (2)0.0624 (8)
C10A0.42772 (18)0.05965 (19)0.12696 (15)0.0453 (6)
C10B0.45656 (19)−0.0687 (2)0.17618 (15)0.0479 (6)
C140.1923 (3)−0.3579 (2)0.1263 (2)0.0715 (9)
H10.65958−0.078270.274660.0820*
H20.64462−0.291830.335040.0916*
H30.44200−0.415580.273290.0813*
H50.134 (3)−0.084 (2)0.0449 (18)0.054 (6)*
H7A0.178780.33949−0.072010.0777*
H7B0.189460.340960.061340.0777*
H8A0.417360.31357−0.042490.1026*
H8B0.379280.441910.017070.1026*
H9A0.435640.326120.192520.1070*
H9B0.561570.367660.138190.1070*
H10A0.591250.154380.083270.0749*
H10B0.599050.159030.216540.0749*
H14A0.18522−0.374730.045260.1074*
H14B0.11011−0.309590.135420.1074*
H14C0.19759−0.440580.167190.1074*
U11U22U33U12U13U23
O60.0446 (8)0.0549 (9)0.0752 (10)−0.0084 (6)−0.0088 (7)0.0151 (7)
N50.0350 (7)0.0400 (8)0.0453 (8)−0.0003 (6)0.0054 (6)0.0036 (6)
C10.0434 (11)0.102 (2)0.0559 (12)0.0226 (12)0.0035 (9)0.0005 (12)
C20.0640 (14)0.107 (2)0.0565 (13)0.0439 (15)0.0101 (10)0.0127 (13)
C30.0818 (17)0.0718 (15)0.0551 (12)0.0387 (13)0.0272 (12)0.0185 (11)
C40.0636 (12)0.0531 (12)0.0473 (10)0.0179 (10)0.0273 (9)0.0090 (8)
C4A0.0408 (9)0.0520 (11)0.0379 (8)0.0101 (8)0.0125 (7)0.0001 (7)
C5A0.0354 (8)0.0431 (10)0.0407 (8)−0.0049 (7)0.0083 (6)−0.0033 (7)
C60.0427 (10)0.0447 (10)0.0442 (9)−0.0046 (8)0.0062 (7)0.0041 (7)
C70.0683 (14)0.0483 (12)0.0718 (14)−0.0129 (10)0.0043 (11)0.0063 (10)
C80.0817 (19)0.0623 (16)0.113 (2)−0.0267 (14)0.0236 (16)0.0034 (15)
C90.0805 (18)0.082 (2)0.0953 (19)−0.0445 (16)0.0002 (15)−0.0061 (15)
C100.0384 (10)0.0861 (17)0.0602 (12)−0.0196 (10)0.0065 (8)−0.0131 (11)
C10A0.0356 (9)0.0608 (12)0.0390 (8)−0.0029 (8)0.0074 (7)−0.0079 (8)
C10B0.0393 (9)0.0648 (13)0.0388 (9)0.0101 (8)0.0073 (7)−0.0038 (8)
C140.095 (2)0.0499 (12)0.0785 (15)0.0098 (12)0.0380 (14)0.0109 (11)
O6—C61.220 (2)C10—C10A1.492 (3)
N5—C4A1.373 (2)C10A—C10B1.421 (3)
N5—C5A1.385 (2)C1—H10.9300
N5—H50.94 (3)C2—H20.9300
C1—C10B1.402 (3)C3—H30.9300
C1—C21.359 (4)C7—H7A0.9700
C2—C31.396 (4)C7—H7B0.9700
C3—C41.374 (3)C8—H8A0.9700
C4—C4A1.401 (3)C8—H8B0.9700
C4—C141.500 (3)C9—H9A0.9700
C4A—C10B1.409 (3)C9—H9B0.9700
C5A—C61.457 (3)C10—H10A0.9700
C5A—C10A1.391 (2)C10—H10B0.9700
C6—C71.507 (3)C14—H14A0.9600
C7—C81.492 (4)C14—H14B0.9600
C8—C91.454 (5)C14—H14C0.9600
C9—C101.514 (4)
O6···N52.684 (2)H5···O62.41 (2)
O6···N5i2.992 (2)H5···C142.94 (2)
O6···H52.41 (2)H5···H14B2.5500
O6···H5i2.11 (3)H5···O6i2.11 (3)
O6···H14Bi2.6300H7A···H10Bvii2.4400
N5···O62.684 (2)H7B···H9A2.5300
N5···O6i2.992 (2)H7B···H14Cviii2.5300
N5···H14B2.8800H8A···H10A2.5400
N5···H10Aii2.9200H8A···C2ii2.9700
C3···C6iii3.560 (3)H8A···C3ii3.0400
C6···C3iv3.560 (3)H9A···H7B2.5300
C10A···C14iv3.484 (3)H9A···H14Biv2.5800
C14···C10Aiii3.484 (3)H10A···H8A2.5400
C1···H10B2.9200H10A···H2v2.5700
C2···H8Aii2.9700H10A···N5ii2.9200
C3···H8Aii3.0400H10A···C4Aii2.9200
C4A···H10Aii2.9200H10B···C12.9200
C10···H2v3.0700H10B···H12.5200
C10···H13.0400H10B···H7Aix2.4400
C10A···H14Civ2.9600H14B···N52.8800
C10B···H14Civ2.9300H14B···H52.5500
C14···H52.94 (2)H14B···H9Aiii2.5800
H1···C103.0400H14B···O6i2.6300
H1···H10B2.5200H14C···H32.4200
H2···C10vi3.0700H14C···H7Bx2.5300
H2···H10Avi2.5700H14C···C10Aiii2.9600
H3···H14C2.4200H14C···C10Biii2.9300
C4A—N5—C5A109.03 (15)C1—C2—H2119.00
C4A—N5—H5128.5 (13)C3—C2—H2119.00
C5A—N5—H5121.0 (13)C2—C3—H3119.00
C2—C1—C10B118.5 (2)C4—C3—H3119.00
C1—C2—C3122.0 (2)C6—C7—H7A107.00
C2—C3—C4122.1 (3)C6—C7—H7B107.00
C4A—C4—C14120.54 (18)C8—C7—H7A107.00
C3—C4—C4A115.7 (2)C8—C7—H7B107.00
C3—C4—C14123.7 (2)H7A—C7—H7B107.00
N5—C4A—C4129.27 (17)C7—C8—H8A107.00
N5—C4A—C10B107.50 (16)C7—C8—H8B107.00
C4—C4A—C10B123.21 (17)C9—C8—H8A107.00
N5—C5A—C6116.80 (15)C9—C8—H8B107.00
C6—C5A—C10A133.99 (17)H8A—C8—H8B107.00
N5—C5A—C10A109.21 (15)C8—C9—H9A108.00
O6—C6—C7118.74 (19)C8—C9—H9B108.00
C5A—C6—C7122.15 (17)C10—C9—H9A108.00
O6—C6—C5A119.02 (17)C10—C9—H9B108.00
C6—C7—C8121.0 (2)H9A—C9—H9B107.00
C7—C8—C9119.6 (3)C9—C10—H10A108.00
C8—C9—C10118.1 (3)C9—C10—H10B108.00
C9—C10—C10A117.22 (19)C10A—C10—H10A108.00
C5A—C10A—C10B106.20 (16)C10A—C10—H10B108.00
C10—C10A—C10B123.93 (17)H10A—C10—H10B107.00
C5A—C10A—C10129.83 (18)C4—C14—H14A109.00
C4A—C10B—C10A108.03 (16)C4—C14—H14B109.00
C1—C10B—C4A118.49 (19)C4—C14—H14C110.00
C1—C10B—C10A133.5 (2)H14A—C14—H14B109.00
C2—C1—H1121.00H14A—C14—H14C109.00
C10B—C1—H1121.00H14B—C14—H14C109.00
C5A—N5—C4A—C4179.17 (18)N5—C5A—C6—C7167.99 (18)
C5A—N5—C4A—C10B−1.88 (19)C10A—C5A—C6—O6172.63 (19)
C4A—N5—C5A—C6−177.17 (15)C10A—C5A—C6—C7−11.0 (3)
C4A—N5—C5A—C10A2.05 (19)N5—C5A—C10A—C10176.20 (19)
C10B—C1—C2—C31.2 (4)N5—C5A—C10A—C10B−1.36 (19)
C2—C1—C10B—C4A−0.1 (3)C6—C5A—C10A—C10−4.8 (3)
C2—C1—C10B—C10A177.7 (2)C6—C5A—C10A—C10B177.67 (18)
C1—C2—C3—C4−0.7 (4)O6—C6—C7—C8−153.2 (2)
C2—C3—C4—C4A−1.0 (3)C5A—C6—C7—C830.4 (3)
C2—C3—C4—C14175.8 (2)C6—C7—C8—C9−60.2 (4)
C3—C4—C4A—N5−179.06 (19)C7—C8—C9—C1075.5 (4)
C3—C4—C4A—C10B2.1 (3)C8—C9—C10—C10A−56.8 (3)
C14—C4—C4A—N54.0 (3)C9—C10—C10A—C5A27.5 (3)
C14—C4—C4A—C10B−174.77 (19)C9—C10—C10A—C10B−155.4 (2)
N5—C4A—C10B—C1179.35 (17)C5A—C10A—C10B—C1−177.8 (2)
N5—C4A—C10B—C10A1.0 (2)C5A—C10A—C10B—C4A0.2 (2)
C4—C4A—C10B—C1−1.6 (3)C10—C10A—C10B—C14.5 (3)
C4—C4A—C10B—C10A−179.94 (17)C10—C10A—C10B—C4A−177.54 (18)
N5—C5A—C6—O6−8.4 (2)
D—H···AD—HH···AD···AD—H···A
N5—H5···O6i0.94 (3)2.11 (3)2.992 (2)156.6 (19)
C10—H10A···Cg1ii0.972.843.736 (2)154
C14—H14C···Cg1iii0.962.863.621 (2)137
C8—H8A···Cg2ii0.972.873.830 (3)173
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N5—H5⋯O6i0.94 (3)2.11 (3)2.992 (2)156.6 (19)
C10—H10A⋯Cg1ii0.972.843.736 (2)154
C14—H14C⋯Cg1iii0.962.863.621 (2)137
C8—H8A⋯Cg2ii0.972.873.830 (3)173

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the pyrrole ring and Cg2 is the centroid of the benzene ring.

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  7,8,9,10-Tetra-hydro-2-methyl-cyclo-hepta-[b]indol-6(5H)-one.

Authors:  Makuteswaran Sridharan; Karnam J Rajendra Prasad; Aimable Ngendahimana; Matthias Zeller
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-06-07

3.  Structure validation in chemical crystallography.

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1.  2,5-Dimethyl-7,8,9,10-tetra-hydro-cyclo-hepta-[b]indol-6(5H)-one.

Authors:  R Archana; E Yamuna; K J Rajendra Prasad; A Thiruvalluvar; R J Butcher
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-23
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