organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-Meth­­oxy-2-methyl-1H-benzo[f]indole-3-carbo­nitrile

aSchool of Chemistry and Biological Engineering, Changsha University of Science & Technology, Changsha 410004, People's Republic of China, and bCollege of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China
*Correspondence e-mail: js_li@yahoo.com.cn

(Received 5 December 2009; accepted 6 December 2009; online 9 December 2009)

Apart from the methyl group of the meth­oxy fragment, the title compound, C15H12N2O, is almost planar (r.m.s. deviation = 0.045 Å); the C atom deviates from the mean plane by 1.216 (1) Å. In the crystal, ππ stacking [shortest centroid–centroid separation = 3.4652 (10) Å] and C—H⋯π inter­actions occur.

Related literature

For the synthesis, see: Du et al. (2008[Du, Y. F., Chang, J. B., Reiner, J. & Zhao, K. (2008). J. Org. Chem. 73, 2007-2010.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12N2O

  • Mr = 236.27

  • Monoclinic, C 2/c

  • a = 18.663 (4) Å

  • b = 7.3763 (15) Å

  • c = 18.589 (4) Å

  • β = 113.46 (3)°

  • V = 2347.6 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.16 mm

Data collection
  • Rigaku Saturn CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.983, Tmax = 0.986

  • 11412 measured reflections

  • 2060 independent reflections

  • 1858 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.094

  • S = 1.04

  • 2060 reflections

  • 166 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.16 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C4–C9 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯Cg3i 0.93 2.65 3.3956 (15) 138
Symmetry code: (i) [x, -y-1, z-{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound, (I), comprises of a benzo ring and its fused indole ring (Fig. 1). The aromatic skeleton is essentially planar.

In the crystal packing, π-π stacking interaction and C—H···π interaction help establish the molecular packing. The shortest centroid-centroid separation is 3.4652 (10) Å, which occurs between the pyrrole parts of the molecules.

Related literature top

For the synthesis, see: Du et al. (2008).

Experimental top

The compound was obtained according to the method of Du and his coworkers (2008). Colourless block of (I) was grown by slow evaporation of its ethanolic solution.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93 and 0.96 Å)and refined as riding with Uiso(H) = 1.2Ueq(CH) or 1.5Ueq(CH3).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing displacement ellipsoids drawn at the 50% probability level.
1-Methoxy-2-methyl-1H-benzo[f]indole-3-carbonitrile top
Crystal data top
C15H12N2OF(000) = 992
Mr = 236.27Dx = 1.337 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3553 reflections
a = 18.663 (4) Åθ = 2.2–27.9°
b = 7.3763 (15) ŵ = 0.09 mm1
c = 18.589 (4) ÅT = 113 K
β = 113.46 (3)°Block, colourless
V = 2347.6 (8) Å30.20 × 0.18 × 0.16 mm
Z = 8
Data collection top
Rigaku Saturn CCD
diffractometer
2060 independent reflections
Radiation source: rotating anode1858 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.035
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 2.4°
ω and ϕ scansh = 2222
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 88
Tmin = 0.983, Tmax = 0.986l = 2222
11412 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0542P)2 + 1.1054P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2060 reflectionsΔρmax = 0.19 e Å3
166 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0212 (18)
Crystal data top
C15H12N2OV = 2347.6 (8) Å3
Mr = 236.27Z = 8
Monoclinic, C2/cMo Kα radiation
a = 18.663 (4) ŵ = 0.09 mm1
b = 7.3763 (15) ÅT = 113 K
c = 18.589 (4) Å0.20 × 0.18 × 0.16 mm
β = 113.46 (3)°
Data collection top
Rigaku Saturn CCD
diffractometer
2060 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
1858 reflections with I > 2σ(I)
Tmin = 0.983, Tmax = 0.986Rint = 0.035
11412 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.04Δρmax = 0.19 e Å3
2060 reflectionsΔρmin = 0.16 e Å3
166 parameters
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
O10.43321 (5)0.84231 (12)0.08385 (5)0.0257 (3)
N10.35813 (6)0.90176 (14)0.06827 (6)0.0203 (3)
N20.11930 (6)1.14000 (15)0.10753 (6)0.0269 (3)
C10.32134 (7)0.87498 (16)0.11865 (7)0.0194 (3)
C20.34992 (7)0.79261 (17)0.19296 (7)0.0223 (3)
H20.40100.75030.21630.027*
C30.29960 (7)0.77742 (16)0.22936 (7)0.0223 (3)
H30.31710.72480.27890.027*
C40.22060 (7)0.83997 (16)0.19371 (7)0.0201 (3)
C50.16852 (7)0.81573 (17)0.23131 (7)0.0235 (3)
H50.18610.75890.28000.028*
C60.09292 (7)0.87424 (18)0.19742 (7)0.0256 (3)
H60.05970.85790.22320.031*
C70.06515 (8)0.95940 (18)0.12338 (7)0.0249 (3)
H70.01381.00020.10080.030*
C80.11331 (7)0.98234 (16)0.08458 (7)0.0208 (3)
H80.09411.03720.03550.025*
C90.19198 (7)0.92382 (15)0.11816 (7)0.0181 (3)
C100.24518 (7)0.93956 (15)0.08037 (7)0.0181 (3)
C110.23885 (7)1.00368 (15)0.00486 (7)0.0185 (3)
C120.31010 (7)0.97803 (16)0.00040 (7)0.0195 (3)
C130.33588 (8)1.02295 (18)0.06433 (7)0.0253 (3)
H13A0.36311.13670.05310.038*
H13B0.29111.03170.11310.038*
H13C0.37000.92950.06810.038*
C140.48901 (8)0.9831 (2)0.12264 (9)0.0327 (4)
H14A0.48181.08290.08730.049*
H14B0.54100.93620.13830.049*
H14C0.48131.02390.16810.049*
C150.17262 (7)1.07923 (16)0.05700 (7)0.0196 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0194 (5)0.0244 (5)0.0344 (5)0.0039 (4)0.0119 (4)0.0008 (4)
N10.0163 (5)0.0211 (5)0.0235 (6)0.0016 (4)0.0079 (4)0.0004 (4)
N20.0258 (6)0.0317 (7)0.0227 (6)0.0015 (5)0.0093 (5)0.0016 (5)
C10.0211 (6)0.0161 (6)0.0216 (6)0.0016 (5)0.0090 (5)0.0021 (5)
C20.0203 (6)0.0193 (6)0.0237 (7)0.0015 (5)0.0049 (5)0.0005 (5)
C30.0274 (7)0.0180 (6)0.0190 (6)0.0013 (5)0.0067 (5)0.0008 (5)
C40.0241 (7)0.0155 (6)0.0201 (6)0.0031 (5)0.0082 (5)0.0034 (5)
C50.0300 (7)0.0205 (6)0.0200 (6)0.0063 (5)0.0100 (5)0.0031 (5)
C60.0265 (7)0.0283 (7)0.0258 (7)0.0094 (6)0.0145 (6)0.0062 (5)
C70.0199 (6)0.0273 (7)0.0259 (7)0.0043 (5)0.0076 (5)0.0063 (5)
C80.0209 (6)0.0200 (6)0.0190 (6)0.0034 (5)0.0054 (5)0.0030 (5)
C90.0203 (6)0.0142 (6)0.0187 (6)0.0042 (5)0.0067 (5)0.0044 (5)
C100.0208 (6)0.0135 (6)0.0188 (6)0.0030 (5)0.0065 (5)0.0033 (5)
C110.0203 (6)0.0158 (6)0.0181 (6)0.0023 (5)0.0064 (5)0.0019 (4)
C120.0227 (7)0.0153 (6)0.0198 (6)0.0026 (5)0.0076 (5)0.0032 (5)
C130.0295 (7)0.0232 (7)0.0262 (7)0.0014 (5)0.0143 (6)0.0012 (5)
C140.0183 (7)0.0371 (8)0.0394 (8)0.0031 (6)0.0079 (6)0.0001 (6)
C150.0225 (7)0.0191 (6)0.0192 (6)0.0034 (5)0.0104 (5)0.0025 (5)
Geometric parameters (Å, º) top
O1—N11.3844 (13)C6—H60.9300
O1—C141.4442 (16)C7—C81.3685 (18)
N1—C121.3559 (16)C7—H70.9300
N1—C11.3784 (16)C8—C91.4149 (18)
N2—C151.1529 (16)C8—H80.9300
C1—C101.3958 (17)C9—C101.4312 (17)
C1—C21.4054 (17)C10—C111.4408 (16)
C2—C31.3631 (19)C11—C121.3846 (18)
C2—H20.9300C11—C151.4245 (18)
C3—C41.4311 (18)C12—C131.4862 (17)
C3—H30.9300C13—H13A0.9600
C4—C51.4163 (18)C13—H13B0.9600
C4—C91.4292 (17)C13—H13C0.9600
C5—C61.3662 (19)C14—H14A0.9600
C5—H50.9300C14—H14B0.9600
C6—C71.4106 (19)C14—H14C0.9600
N1—O1—C14110.19 (9)C9—C8—H8119.5
C12—N1—C1112.19 (10)C8—C9—C4118.80 (11)
C12—N1—O1124.28 (10)C8—C9—C10124.02 (11)
C1—N1—O1123.30 (10)C4—C9—C10117.16 (11)
N1—C1—C10106.64 (11)C1—C10—C9119.12 (11)
N1—C1—C2129.27 (11)C1—C10—C11106.30 (11)
C10—C1—C2124.03 (12)C9—C10—C11134.51 (11)
C3—C2—C1117.16 (11)C12—C11—C15123.07 (11)
C3—C2—H2121.4C12—C11—C10108.38 (11)
C1—C2—H2121.4C15—C11—C10128.54 (11)
C2—C3—C4122.01 (12)N1—C12—C11106.49 (11)
C2—C3—H3119.0N1—C12—C13122.83 (11)
C4—C3—H3119.0C11—C12—C13130.67 (12)
C5—C4—C9118.56 (11)C12—C13—H13A109.5
C5—C4—C3120.91 (11)C12—C13—H13B109.5
C9—C4—C3120.51 (11)H13A—C13—H13B109.5
C6—C5—C4121.21 (12)C12—C13—H13C109.5
C6—C5—H5119.4H13A—C13—H13C109.5
C4—C5—H5119.4H13B—C13—H13C109.5
C5—C6—C7120.10 (12)O1—C14—H14A109.5
C5—C6—H6120.0O1—C14—H14B109.5
C7—C6—H6120.0H14A—C14—H14B109.5
C8—C7—C6120.40 (12)O1—C14—H14C109.5
C8—C7—H7119.8H14A—C14—H14C109.5
C6—C7—H7119.8H14B—C14—H14C109.5
C7—C8—C9120.91 (12)N2—C15—C11179.39 (13)
C7—C8—H8119.5
C14—O1—N1—C1293.87 (13)N1—C1—C10—C9178.00 (10)
C14—O1—N1—C192.15 (13)C2—C1—C10—C90.53 (18)
C12—N1—C1—C100.59 (13)N1—C1—C10—C110.58 (12)
O1—N1—C1—C10175.22 (10)C2—C1—C10—C11176.89 (11)
C12—N1—C1—C2176.70 (12)C8—C9—C10—C1179.17 (11)
O1—N1—C1—C22.08 (19)C4—C9—C10—C10.57 (16)
N1—C1—C2—C3177.49 (11)C8—C9—C10—C112.7 (2)
C10—C1—C2—C30.62 (18)C4—C9—C10—C11175.95 (12)
C1—C2—C3—C40.78 (18)C1—C10—C11—C120.40 (13)
C2—C3—C4—C5177.32 (11)C9—C10—C11—C12177.24 (12)
C2—C3—C4—C90.89 (18)C1—C10—C11—C15178.68 (11)
C9—C4—C5—C61.41 (18)C9—C10—C11—C151.8 (2)
C3—C4—C5—C6179.65 (11)C1—N1—C12—C110.33 (13)
C4—C5—C6—C70.48 (19)O1—N1—C12—C11174.90 (10)
C5—C6—C7—C80.70 (19)C1—N1—C12—C13179.24 (11)
C6—C7—C8—C90.91 (18)O1—N1—C12—C136.20 (18)
C7—C8—C9—C40.04 (17)C15—C11—C12—N1179.09 (10)
C7—C8—C9—C10178.54 (11)C10—C11—C12—N10.05 (13)
C5—C4—C9—C81.18 (17)C15—C11—C12—C132.1 (2)
C3—C4—C9—C8179.42 (10)C10—C11—C12—C13178.73 (12)
C5—C4—C9—C10177.50 (10)C12—C11—C15—N220 (14)
C3—C4—C9—C100.75 (17)C10—C11—C15—N2159 (14)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C4–C9 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg3i0.932.653.3956 (15)138
Symmetry code: (i) x, y1, z1/2.

Experimental details

Crystal data
Chemical formulaC15H12N2O
Mr236.27
Crystal system, space groupMonoclinic, C2/c
Temperature (K)113
a, b, c (Å)18.663 (4), 7.3763 (15), 18.589 (4)
β (°) 113.46 (3)
V3)2347.6 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.18 × 0.16
Data collection
DiffractometerRigaku Saturn CCD
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.983, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
11412, 2060, 1858
Rint0.035
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.094, 1.04
No. of reflections2060
No. of parameters166
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.16

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C4–C9 ring.
D—H···AD—HH···AD···AD—H···A
C3—H3···Cg3i0.932.653.3956 (15)138
Symmetry code: (i) x, y1, z1/2.
 

References

First citationDu, Y. F., Chang, J. B., Reiner, J. & Zhao, K. (2008). J. Org. Chem. 73, 2007–2010.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationRigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds