2-Methyl-3-p-tolyl-3H-benzo[e]indole-1-carbonitrile.

In the title compound, C(21)H(16)N(2), the dihedral angle between the benzoindole and tosyl ring systems is 71.99 (7)°. In the crystal, mol-ecules are linked into centrosymmetric dimers by pairs of C-H⋯N hydrogen bonds, generating R(2) (2)(16) loops.

Related literature

For the synthesis, see: Du et al. (2006 ▶).

Experimental

Crystal data

C21n class="CellLine">H16N2

M = 296.36

Monoclinic,

a = 10.321 (2) Å

b = 12.422 (3) Å

c = 13.258 (3) Å

β = 107.14 (3)°

V = 1624.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.28 × 0.20 × 0.18 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.980, T max = 0.987

10714 measured reflections

2858 independent reflections

2092 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.168

S = 1.04

2858 reflections

210 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/S1600536809052441/hb5275sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052441/hb5275Isup2.hkl

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

C21H16N2	F(000) = 624
Mr = 296.36	Dx = 1.212 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3474 reflections
a = 10.321 (2) Å	θ = 2.2–27.5°
b = 12.422 (3) Å	µ = 0.07 mm−1
c = 13.258 (3) Å	T = 293 K
β = 107.14 (3)°	Block, colourless
V = 1624.4 (6) Å3	0.28 × 0.20 × 0.18 mm
Z = 4

Rigaku Saturn CCD diffractometer	2858 independent reflections
Radiation source: rotating anode	2092 reflections with I > 2σ(I)
confocal	Rint = 0.036
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.2°
ω and φ scans	h = −12→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→14
Tmin = 0.980, Tmax = 0.987	l = −15→14
10714 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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.168	w = 1/[σ2(Fo2) + (0.1027P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2858 reflections	Δρmax = 0.19 e Å−3
210 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: 0.070 (10)

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
N1	0.10089 (15)	0.87702 (12)	0.23973 (11)	0.0575 (5)
N2	−0.2675 (2)	1.06928 (18)	0.01735 (16)	0.1025 (8)
C1	0.00439 (18)	0.79674 (14)	0.23281 (13)	0.0547 (5)
C2	0.0217 (2)	0.69469 (15)	0.27979 (14)	0.0629 (5)
H2	0.1053	0.6728	0.3241	0.075*
C3	−0.0883 (2)	0.62878 (16)	0.25826 (15)	0.0679 (6)
H3	−0.0790	0.5606	0.2885	0.081*
C4	−0.2171 (2)	0.66084 (17)	0.19091 (15)	0.0631 (6)
C5	−0.3298 (2)	0.5901 (2)	0.16630 (16)	0.0806 (7)
H5	−0.3197	0.5211	0.1947	0.097*
C6	−0.4540 (2)	0.6220 (2)	0.10095 (19)	0.0900 (8)
H6	−0.5266	0.5742	0.0854	0.108*
C7	−0.4715 (2)	0.7253 (2)	0.05799 (18)	0.0860 (7)
H7	−0.5561	0.7467	0.0150	0.103*
C8	−0.3656 (2)	0.79452 (19)	0.07884 (15)	0.0692 (6)
H8	−0.3783	0.8630	0.0491	0.083*
C9	−0.23647 (19)	0.76498 (16)	0.14464 (13)	0.0580 (5)
C10	−0.12000 (19)	0.83318 (14)	0.16682 (12)	0.0542 (5)
C11	−0.0941 (2)	0.93897 (14)	0.13370 (13)	0.0589 (5)
C12	0.0402 (2)	0.96343 (15)	0.17945 (14)	0.0608 (5)
C13	0.1146 (3)	1.06418 (17)	0.17368 (17)	0.0812 (7)
H13A	0.1546	1.0918	0.2436	0.122*
H13B	0.0529	1.1164	0.1323	0.122*
H13C	0.1847	1.0496	0.1414	0.122*
C14	−0.1898 (2)	1.01126 (18)	0.06895 (15)	0.0722 (6)
C15	0.24140 (19)	0.86902 (14)	0.29878 (14)	0.0556 (5)
C16	0.3392 (2)	0.85881 (17)	0.24716 (15)	0.0670 (6)
H16	0.3146	0.8569	0.1738	0.080*
C17	0.4734 (2)	0.85143 (16)	0.30554 (17)	0.0722 (6)
H17	0.5388	0.8442	0.2704	0.087*
C18	0.5142 (2)	0.85442 (15)	0.41425 (17)	0.0670 (6)
C19	0.4147 (2)	0.86356 (17)	0.46373 (16)	0.0717 (6)
H19	0.4395	0.8647	0.5371	0.086*
C20	0.2793 (2)	0.87108 (16)	0.40767 (14)	0.0661 (6)
H20	0.2140	0.8775	0.4430	0.079*
C21	0.6620 (2)	0.8465 (2)	0.4766 (2)	0.1000 (9)
H21A	0.6952	0.7759	0.4682	0.150*
H21B	0.6720	0.8594	0.5499	0.150*
H21C	0.7128	0.8993	0.4513	0.150*

	U11	U22	U33	U12	U13	U23
N1	0.0540 (10)	0.0542 (9)	0.0598 (9)	0.0010 (7)	0.0098 (7)	0.0032 (7)
N2	0.1048 (18)	0.1026 (16)	0.0931 (13)	0.0401 (13)	0.0185 (12)	0.0307 (12)
C1	0.0532 (11)	0.0564 (11)	0.0521 (9)	0.0020 (9)	0.0115 (8)	0.0003 (8)
C2	0.0582 (12)	0.0630 (12)	0.0618 (11)	0.0065 (10)	0.0091 (9)	0.0085 (9)
C3	0.0706 (15)	0.0630 (12)	0.0686 (12)	−0.0020 (10)	0.0181 (10)	0.0123 (9)
C4	0.0561 (13)	0.0752 (14)	0.0595 (11)	−0.0083 (10)	0.0193 (9)	−0.0022 (9)
C5	0.0756 (17)	0.0909 (16)	0.0801 (13)	−0.0151 (13)	0.0306 (12)	−0.0002 (11)
C6	0.0581 (16)	0.124 (2)	0.0903 (16)	−0.0246 (14)	0.0249 (13)	−0.0114 (15)
C7	0.0544 (14)	0.123 (2)	0.0797 (14)	−0.0008 (13)	0.0185 (11)	−0.0047 (14)
C8	0.0516 (12)	0.0883 (15)	0.0654 (12)	0.0054 (11)	0.0137 (9)	−0.0024 (10)
C9	0.0517 (12)	0.0728 (13)	0.0502 (10)	0.0031 (9)	0.0162 (8)	−0.0029 (8)
C10	0.0531 (11)	0.0601 (11)	0.0475 (9)	0.0074 (9)	0.0120 (8)	−0.0010 (7)
C11	0.0616 (13)	0.0571 (11)	0.0550 (10)	0.0116 (9)	0.0128 (9)	0.0036 (8)
C12	0.0653 (13)	0.0532 (11)	0.0628 (10)	0.0061 (9)	0.0171 (9)	0.0013 (8)
C13	0.0884 (17)	0.0583 (13)	0.0960 (14)	−0.0013 (11)	0.0257 (13)	0.0075 (11)
C14	0.0755 (15)	0.0725 (14)	0.0667 (12)	0.0194 (11)	0.0181 (10)	0.0103 (10)
C15	0.0481 (11)	0.0550 (11)	0.0584 (10)	−0.0029 (8)	0.0078 (8)	−0.0001 (8)
C16	0.0665 (14)	0.0746 (13)	0.0614 (11)	0.0013 (10)	0.0213 (10)	−0.0024 (9)
C17	0.0578 (14)	0.0732 (14)	0.0902 (15)	0.0001 (10)	0.0288 (11)	−0.0033 (10)
C18	0.0535 (13)	0.0555 (12)	0.0852 (14)	−0.0010 (9)	0.0102 (11)	0.0016 (10)
C19	0.0628 (14)	0.0818 (14)	0.0627 (11)	−0.0043 (11)	0.0062 (10)	0.0005 (10)
C20	0.0564 (13)	0.0825 (14)	0.0593 (11)	−0.0021 (10)	0.0169 (9)	0.0014 (9)
C21	0.0563 (15)	0.0937 (18)	0.133 (2)	0.0003 (12)	0.0011 (14)	0.0023 (15)

N1—C12	1.374 (2)	C10—C11	1.435 (3)
N1—C1	1.393 (2)	C11—C12	1.373 (3)
N1—C15	1.434 (2)	C11—C14	1.421 (3)
N2—C14	1.143 (2)	C12—C13	1.483 (3)
C1—C10	1.399 (2)	C13—H13A	0.9600
C1—C2	1.400 (2)	C13—H13B	0.9600
C2—C3	1.360 (3)	C13—H13C	0.9600
C2—H2	0.9300	C15—C20	1.380 (3)
C3—C4	1.422 (3)	C15—C16	1.382 (3)
C3—H3	0.9300	C16—C17	1.376 (3)
C4—C5	1.417 (3)	C16—H16	0.9300
C4—C9	1.420 (3)	C17—C18	1.378 (3)
C5—C6	1.377 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.376 (3)
C6—C7	1.394 (4)	C18—C21	1.509 (3)
C6—H6	0.9300	C19—C20	1.379 (3)
C7—C8	1.354 (3)	C19—H19	0.9300
C7—H7	0.9300	C20—H20	0.9300
C8—C9	1.409 (3)	C21—H21A	0.9600
C8—H8	0.9300	C21—H21B	0.9600
C9—C10	1.429 (3)	C21—H21C	0.9600
C12—N1—C1	109.04 (15)	C14—C11—C10	127.20 (19)
C12—N1—C15	125.88 (15)	C11—C12—N1	108.18 (17)
C1—N1—C15	125.07 (14)	C11—C12—C13	129.44 (18)
N1—C1—C10	108.42 (15)	N1—C12—C13	122.34 (18)
N1—C1—C2	128.59 (17)	C12—C13—H13A	109.5
C10—C1—C2	122.97 (17)	C12—C13—H13B	109.5
C3—C2—C1	117.55 (18)	H13A—C13—H13B	109.5
C3—C2—H2	121.2	C12—C13—H13C	109.5
C1—C2—H2	121.2	H13A—C13—H13C	109.5
C2—C3—C4	122.07 (18)	H13B—C13—H13C	109.5
C2—C3—H3	119.0	N2—C14—C11	179.4 (3)
C4—C3—H3	119.0	C20—C15—C16	119.78 (18)
C5—C4—C9	117.6 (2)	C20—C15—N1	119.91 (18)
C5—C4—C3	121.5 (2)	C16—C15—N1	120.31 (16)
C9—C4—C3	120.85 (18)	C17—C16—C15	119.24 (17)
C6—C5—C4	121.0 (2)	C17—C16—H16	120.4
C6—C5—H5	119.5	C15—C16—H16	120.4
C4—C5—H5	119.5	C16—C17—C18	122.2 (2)
C5—C6—C7	120.4 (2)	C16—C17—H17	118.9
C5—C6—H6	119.8	C18—C17—H17	118.9
C7—C6—H6	119.8	C19—C18—C17	117.41 (19)
C8—C7—C6	120.1 (2)	C19—C18—C21	121.3 (2)
C8—C7—H7	120.0	C17—C18—C21	121.2 (2)
C6—C7—H7	120.0	C18—C19—C20	121.91 (19)
C7—C8—C9	121.4 (2)	C18—C19—H19	119.0
C7—C8—H8	119.3	C20—C19—H19	119.0
C9—C8—H8	119.3	C19—C20—C15	119.5 (2)
C8—C9—C4	119.45 (19)	C19—C20—H20	120.3
C8—C9—C10	123.90 (19)	C15—C20—H20	120.3
C4—C9—C10	116.63 (17)	C18—C21—H21A	109.5
C1—C10—C9	119.89 (17)	C18—C21—H21B	109.4
C1—C10—C11	105.56 (17)	H21A—C21—H21B	109.5
C9—C10—C11	134.53 (16)	C18—C21—H21C	109.4
C12—C11—C14	123.93 (19)	H21A—C21—H21C	109.5
C12—C11—C10	108.80 (15)	H21B—C21—H21C	109.5
C12—N1—C1—C10	−0.03 (19)	C1—C10—C11—C12	−0.5 (2)
C15—N1—C1—C10	−178.86 (14)	C9—C10—C11—C12	−178.67 (19)
C12—N1—C1—C2	178.88 (18)	C1—C10—C11—C14	−177.42 (17)
C15—N1—C1—C2	0.0 (3)	C9—C10—C11—C14	4.4 (3)
N1—C1—C2—C3	−177.95 (18)	C14—C11—C12—N1	177.53 (16)
C10—C1—C2—C3	0.8 (3)	C10—C11—C12—N1	0.5 (2)
C1—C2—C3—C4	−0.1 (3)	C14—C11—C12—C13	0.0 (3)
C2—C3—C4—C5	177.9 (2)	C10—C11—C12—C13	−177.0 (2)
C2—C3—C4—C9	−1.2 (3)	C1—N1—C12—C11	−0.3 (2)
C9—C4—C5—C6	−0.8 (3)	C15—N1—C12—C11	178.55 (16)
C3—C4—C5—C6	−179.95 (19)	C1—N1—C12—C13	177.43 (18)
C4—C5—C6—C7	−0.4 (4)	C15—N1—C12—C13	−3.8 (3)
C5—C6—C7—C8	1.2 (4)	C12—C11—C14—N2	−129 (29)
C6—C7—C8—C9	−0.7 (3)	C10—C11—C14—N2	47 (29)
C7—C8—C9—C4	−0.6 (3)	C12—N1—C15—C20	110.1 (2)
C7—C8—C9—C10	177.95 (18)	C1—N1—C15—C20	−71.3 (2)
C5—C4—C9—C8	1.3 (3)	C12—N1—C15—C16	−70.1 (2)
C3—C4—C9—C8	−179.57 (17)	C1—N1—C15—C16	108.5 (2)
C5—C4—C9—C10	−177.31 (17)	C20—C15—C16—C17	−0.4 (3)
C3—C4—C9—C10	1.8 (3)	N1—C15—C16—C17	179.90 (17)
N1—C1—C10—C9	178.82 (15)	C15—C16—C17—C18	−0.3 (3)
C2—C1—C10—C9	−0.2 (3)	C16—C17—C18—C19	1.0 (3)
N1—C1—C10—C11	0.30 (19)	C16—C17—C18—C21	−179.8 (2)
C2—C1—C10—C11	−178.68 (16)	C17—C18—C19—C20	−0.9 (3)
C8—C9—C10—C1	−179.70 (15)	C21—C18—C19—C20	179.9 (2)
C4—C9—C10—C1	−1.1 (2)	C18—C19—C20—C15	0.3 (3)
C8—C9—C10—C11	−1.7 (3)	C16—C15—C20—C19	0.4 (3)
C4—C9—C10—C11	176.86 (18)	N1—C15—C20—C19	−179.86 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N2i	0.93	2.60	3.480 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯N2i	0.93	2.60	3.480 (3)	158

Symmetry code: (i) .