1-Meth-oxy-2-methyl-1H-benzo[f]indole-3-carbonitrile.

Apart from the methyl group of the meth-oxy fragment, the title compound, C(15)H(12)N(2)O, 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, π-π stacking [shortest centroid-centroid separation = 3.4652 (10) Å] and C-H⋯π inter-actions occur.

Related literature

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

Experimental

Crystal data

C15H12N2O

M = 236.27

Monoclinic,

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 ▶) T min = 0.983, T max = 0.986

11412 measured reflections

2060 independent reflections

1858 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 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

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052416/hb5274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052416/hb5274Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H12N2O	F(000) = 992
Mr = 236.27	Dx = 1.337 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3553 reflections
a = 18.663 (4) Å	θ = 2.2–27.9°
b = 7.3763 (15) Å	µ = 0.09 mm−1
c = 18.589 (4) Å	T = 113 K
β = 113.46 (3)°	Block, colourless
V = 2347.6 (8) Å3	0.20 × 0.18 × 0.16 mm
Z = 8

Rigaku Saturn CCD diffractometer	2060 independent reflections
Radiation source: rotating anode	1858 reflections with I > 2σ(I)
confocal	Rint = 0.035
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω and φ scans	h = −22→22
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −8→8
Tmin = 0.983, Tmax = 0.986	l = −22→22
11412 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-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 reflections	Δρmax = 0.19 e Å−3
166 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0212 (18)

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.

	x	y	z	Uiso*/Ueq
O1	0.43321 (5)	0.84231 (12)	0.08385 (5)	0.0257 (3)
N1	0.35813 (6)	0.90176 (14)	0.06827 (6)	0.0203 (3)
N2	0.11930 (6)	1.14000 (15)	−0.10753 (6)	0.0269 (3)
C1	0.32134 (7)	0.87498 (16)	0.11865 (7)	0.0194 (3)
C2	0.34992 (7)	0.79261 (17)	0.19296 (7)	0.0223 (3)
H2	0.4010	0.7503	0.2163	0.027*
C3	0.29960 (7)	0.77742 (16)	0.22936 (7)	0.0223 (3)
H3	0.3171	0.7248	0.2789	0.027*
C4	0.22060 (7)	0.83997 (16)	0.19371 (7)	0.0201 (3)
C5	0.16852 (7)	0.81573 (17)	0.23131 (7)	0.0235 (3)
H5	0.1861	0.7589	0.2800	0.028*
C6	0.09292 (7)	0.87424 (18)	0.19742 (7)	0.0256 (3)
H6	0.0597	0.8579	0.2232	0.031*
C7	0.06515 (8)	0.95940 (18)	0.12338 (7)	0.0249 (3)
H7	0.0138	1.0002	0.1008	0.030*
C8	0.11331 (7)	0.98234 (16)	0.08458 (7)	0.0208 (3)
H8	0.0941	1.0372	0.0355	0.025*
C9	0.19198 (7)	0.92382 (15)	0.11816 (7)	0.0181 (3)
C10	0.24518 (7)	0.93956 (15)	0.08037 (7)	0.0181 (3)
C11	0.23885 (7)	1.00368 (15)	0.00486 (7)	0.0185 (3)
C12	0.31010 (7)	0.97803 (16)	−0.00040 (7)	0.0195 (3)
C13	0.33588 (8)	1.02295 (18)	−0.06433 (7)	0.0253 (3)
H13A	0.3631	1.1367	−0.0531	0.038*
H13B	0.2911	1.0317	−0.1131	0.038*
H13C	0.3700	0.9295	−0.0681	0.038*
C14	0.48901 (8)	0.9831 (2)	0.12264 (9)	0.0327 (4)
H14A	0.4818	1.0829	0.0873	0.049*
H14B	0.5410	0.9362	0.1383	0.049*
H14C	0.4813	1.0239	0.1681	0.049*
C15	0.17262 (7)	1.07923 (16)	−0.05700 (7)	0.0196 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0194 (5)	0.0244 (5)	0.0344 (5)	0.0039 (4)	0.0119 (4)	−0.0008 (4)
N1	0.0163 (5)	0.0211 (5)	0.0235 (6)	0.0016 (4)	0.0079 (4)	−0.0004 (4)
N2	0.0258 (6)	0.0317 (7)	0.0227 (6)	0.0015 (5)	0.0093 (5)	0.0016 (5)
C1	0.0211 (6)	0.0161 (6)	0.0216 (6)	−0.0016 (5)	0.0090 (5)	−0.0021 (5)
C2	0.0203 (6)	0.0193 (6)	0.0237 (7)	0.0015 (5)	0.0049 (5)	−0.0005 (5)
C3	0.0274 (7)	0.0180 (6)	0.0190 (6)	−0.0013 (5)	0.0067 (5)	0.0008 (5)
C4	0.0241 (7)	0.0155 (6)	0.0201 (6)	−0.0031 (5)	0.0082 (5)	−0.0034 (5)
C5	0.0300 (7)	0.0205 (6)	0.0200 (6)	−0.0063 (5)	0.0100 (5)	−0.0031 (5)
C6	0.0265 (7)	0.0283 (7)	0.0258 (7)	−0.0094 (6)	0.0145 (6)	−0.0062 (5)
C7	0.0199 (6)	0.0273 (7)	0.0259 (7)	−0.0043 (5)	0.0076 (5)	−0.0063 (5)
C8	0.0209 (6)	0.0200 (6)	0.0190 (6)	−0.0034 (5)	0.0054 (5)	−0.0030 (5)
C9	0.0203 (6)	0.0142 (6)	0.0187 (6)	−0.0042 (5)	0.0067 (5)	−0.0044 (5)
C10	0.0208 (6)	0.0135 (6)	0.0188 (6)	−0.0030 (5)	0.0065 (5)	−0.0033 (5)
C11	0.0203 (6)	0.0158 (6)	0.0181 (6)	−0.0023 (5)	0.0064 (5)	−0.0019 (4)
C12	0.0227 (7)	0.0153 (6)	0.0198 (6)	−0.0026 (5)	0.0076 (5)	−0.0032 (5)
C13	0.0295 (7)	0.0232 (7)	0.0262 (7)	−0.0014 (5)	0.0143 (6)	−0.0012 (5)
C14	0.0183 (7)	0.0371 (8)	0.0394 (8)	−0.0031 (6)	0.0079 (6)	−0.0001 (6)
C15	0.0225 (7)	0.0191 (6)	0.0192 (6)	−0.0034 (5)	0.0104 (5)	−0.0025 (5)

O1—N1	1.3844 (13)	C6—H6	0.9300
O1—C14	1.4442 (16)	C7—C8	1.3685 (18)
N1—C12	1.3559 (16)	C7—H7	0.9300
N1—C1	1.3784 (16)	C8—C9	1.4149 (18)
N2—C15	1.1529 (16)	C8—H8	0.9300
C1—C10	1.3958 (17)	C9—C10	1.4312 (17)
C1—C2	1.4054 (17)	C10—C11	1.4408 (16)
C2—C3	1.3631 (19)	C11—C12	1.3846 (18)
C2—H2	0.9300	C11—C15	1.4245 (18)
C3—C4	1.4311 (18)	C12—C13	1.4862 (17)
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.4163 (18)	C13—H13B	0.9600
C4—C9	1.4292 (17)	C13—H13C	0.9600
C5—C6	1.3662 (19)	C14—H14A	0.9600
C5—H5	0.9300	C14—H14B	0.9600
C6—C7	1.4106 (19)	C14—H14C	0.9600
N1—O1—C14	110.19 (9)	C9—C8—H8	119.5
C12—N1—C1	112.19 (10)	C8—C9—C4	118.80 (11)
C12—N1—O1	124.28 (10)	C8—C9—C10	124.02 (11)
C1—N1—O1	123.30 (10)	C4—C9—C10	117.16 (11)
N1—C1—C10	106.64 (11)	C1—C10—C9	119.12 (11)
N1—C1—C2	129.27 (11)	C1—C10—C11	106.30 (11)
C10—C1—C2	124.03 (12)	C9—C10—C11	134.51 (11)
C3—C2—C1	117.16 (11)	C12—C11—C15	123.07 (11)
C3—C2—H2	121.4	C12—C11—C10	108.38 (11)
C1—C2—H2	121.4	C15—C11—C10	128.54 (11)
C2—C3—C4	122.01 (12)	N1—C12—C11	106.49 (11)
C2—C3—H3	119.0	N1—C12—C13	122.83 (11)
C4—C3—H3	119.0	C11—C12—C13	130.67 (12)
C5—C4—C9	118.56 (11)	C12—C13—H13A	109.5
C5—C4—C3	120.91 (11)	C12—C13—H13B	109.5
C9—C4—C3	120.51 (11)	H13A—C13—H13B	109.5
C6—C5—C4	121.21 (12)	C12—C13—H13C	109.5
C6—C5—H5	119.4	H13A—C13—H13C	109.5
C4—C5—H5	119.4	H13B—C13—H13C	109.5
C5—C6—C7	120.10 (12)	O1—C14—H14A	109.5
C5—C6—H6	120.0	O1—C14—H14B	109.5
C7—C6—H6	120.0	H14A—C14—H14B	109.5
C8—C7—C6	120.40 (12)	O1—C14—H14C	109.5
C8—C7—H7	119.8	H14A—C14—H14C	109.5
C6—C7—H7	119.8	H14B—C14—H14C	109.5
C7—C8—C9	120.91 (12)	N2—C15—C11	179.39 (13)
C7—C8—H8	119.5
C14—O1—N1—C12	93.87 (13)	N1—C1—C10—C9	178.00 (10)
C14—O1—N1—C1	−92.15 (13)	C2—C1—C10—C9	0.53 (18)
C12—N1—C1—C10	−0.59 (13)	N1—C1—C10—C11	0.58 (12)
O1—N1—C1—C10	−175.22 (10)	C2—C1—C10—C11	−176.89 (11)
C12—N1—C1—C2	176.70 (12)	C8—C9—C10—C1	−179.17 (11)
O1—N1—C1—C2	2.08 (19)	C4—C9—C10—C1	−0.57 (16)
N1—C1—C2—C3	−177.49 (11)	C8—C9—C10—C11	−2.7 (2)
C10—C1—C2—C3	−0.62 (18)	C4—C9—C10—C11	175.95 (12)
C1—C2—C3—C4	0.78 (18)	C1—C10—C11—C12	−0.40 (13)
C2—C3—C4—C5	177.32 (11)	C9—C10—C11—C12	−177.24 (12)
C2—C3—C4—C9	−0.89 (18)	C1—C10—C11—C15	178.68 (11)
C9—C4—C5—C6	−1.41 (18)	C9—C10—C11—C15	1.8 (2)
C3—C4—C5—C6	−179.65 (11)	C1—N1—C12—C11	0.33 (13)
C4—C5—C6—C7	0.48 (19)	O1—N1—C12—C11	174.90 (10)
C5—C6—C7—C8	0.70 (19)	C1—N1—C12—C13	179.24 (11)
C6—C7—C8—C9	−0.91 (18)	O1—N1—C12—C13	−6.20 (18)
C7—C8—C9—C4	−0.04 (17)	C15—C11—C12—N1	−179.09 (10)
C7—C8—C9—C10	178.54 (11)	C10—C11—C12—N1	0.05 (13)
C5—C4—C9—C8	1.18 (17)	C15—C11—C12—C13	2.1 (2)
C3—C4—C9—C8	179.42 (10)	C10—C11—C12—C13	−178.73 (12)
C5—C4—C9—C10	−177.50 (10)	C12—C11—C15—N2	20 (14)
C3—C4—C9—C10	0.75 (17)	C10—C11—C15—N2	−159 (14)

Cg3 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg3i	0.93	2.65	3.3956 (15)	138

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg3i	0.93	2.65	3.3956 (15)	138

Symmetry code: (i) .