Photochemical formation of 2-acetyl-7-methyl­benz­[e]­indole

The title compound, C₁₅H₁₃NO, was obtained on irradiation of N-acetyl-2-(2-methyl­styryl)­pyrrole. It was characterized spectroscopically and by X-ray diffraction. The mol­ecule is a planar system of three annelated rings (toluene, benzene and pyrrole). An intermolecular hydrogen bond (N—H...O) is observed, connecting mol­ecules into a chain.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.056
• wR factor = 0.168
• Data-to-parameter ratio = 8.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           74.87
         From the CIF: _reflns_number_total               1398
         Count of symmetry unique reflns         1398
         Completeness (_total/calc)            100.00%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 and CELDIM in CAD-4 Software; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SIR97 (Altomare et al.,1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1990).

2-acetyl-7-methylbenzo[e]indol

Crystal data

C15H13NO	F(000) = 472
Mr = 223.26	Dx = 1.283 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.8710 (6) Å	θ = 9.5–21.9°
b = 8.835 (1) Å	µ = 0.63 mm^−1
c = 19.042 (2) Å	T = 293 K
V = 1156.0 (2) Å^3	Prismatic, colourless
Z = 4	0.14 × 0.12 × 0.09 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	Rint = 0.000
Radiation source: X-ray tube	θmax = 74.9°, θmin = 4.6°
Graphite monochromator	h = −8→0
θ/2θ scans	k = −11→0
1398 measured reflections	l = 0→23
1398 independent reflections	3 standard reflections every 120 min
1030 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: see text
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.1015P)^2 + 0.0534P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
1398 reflections	Δρmax = 0.31 e Å^−3
161 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
O16	0.4065 (4)	0.3058 (3)	0.49174 (10)	0.0671 (10)
N1	0.6746 (5)	0.2657 (4)	0.38581 (10)	0.0531 (9)
C2	0.5065 (6)	0.3463 (4)	0.37681 (10)	0.0515 (10)
C3	0.4966 (6)	0.3931 (4)	0.30747 (10)	0.0558 (11)
C4	0.6653 (6)	0.3403 (4)	0.27382 (10)	0.0495 (11)
C5	0.7746 (6)	0.2627 (4)	0.32379 (10)	0.0509 (11)
C6	0.9552 (6)	0.1946 (5)	0.30861 (10)	0.0603 (11)
C7	1.0233 (7)	0.2091 (5)	0.2426 (2)	0.0647 (12)
C8	0.9215 (6)	0.2881 (4)	0.18892 (10)	0.0560 (11)
C9	0.7400 (6)	0.3553 (5)	0.20343 (10)	0.0543 (11)
C10	0.6397 (7)	0.4350 (5)	0.15009 (10)	0.0680 (16)
C11	0.7213 (9)	0.4440 (6)	0.0844 (2)	0.0810 (18)
C12	0.9004 (9)	0.3774 (6)	0.0700 (2)	0.0773 (18)
C13	0.9992 (7)	0.3031 (5)	0.1199 (2)	0.0670 (14)
C14	1.1864 (13)	0.2332 (9)	0.1026 (3)	0.141 (3)
C15	0.3726 (6)	0.3663 (5)	0.43452 (10)	0.0558 (11)
C17	0.1949 (7)	0.4619 (6)	0.4232 (2)	0.0787 (17)
H1	0.719 (7)	0.226 (5)	0.430 (2)	0.073 (13)*
H3	0.396890	0.449020	0.287030	0.0670*
H6	1.024460	0.141890	0.342700	0.0724*
H7	1.142580	0.165270	0.231580	0.0777*
H10	0.520460	0.480500	0.159390	0.0817*
H11	0.655690	0.495400	0.048910	0.0970*
H12	0.952300	0.384600	0.025010	0.0929*
H14A	1.181730	0.127150	0.113530	0.2112*
H14B	1.287750	0.280490	0.129430	0.2112*
H14C	1.212400	0.245970	0.053390	0.2112*
H17A	0.088130	0.420710	0.449540	0.1180*
H17B	0.162420	0.462870	0.374190	0.1180*
H17C	0.220380	0.563410	0.438720	0.1180*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O16	0.0705 (17)	0.079 (2)	0.0517 (14)	0.0013 (16)	0.0074 (14)	0.0084 (14)
N1	0.0567 (17)	0.0609 (18)	0.0417 (14)	0.0046 (16)	−0.0049 (13)	0.0078 (14)
C2	0.0513 (18)	0.0566 (19)	0.0466 (16)	0.0000 (18)	−0.0017 (16)	0.0049 (15)
C3	0.0544 (19)	0.064 (2)	0.0490 (18)	0.003 (2)	−0.0053 (17)	0.0142 (17)
C4	0.0525 (19)	0.052 (2)	0.0440 (16)	−0.0042 (17)	−0.0054 (15)	0.0052 (15)
C5	0.056 (2)	0.053 (2)	0.0437 (16)	−0.0001 (17)	−0.0033 (15)	0.0063 (15)
C6	0.059 (2)	0.069 (2)	0.0528 (19)	0.010 (2)	−0.0047 (17)	0.0055 (19)
C7	0.064 (2)	0.068 (2)	0.062 (2)	0.009 (2)	0.0061 (19)	−0.0009 (19)
C8	0.065 (2)	0.055 (2)	0.0481 (18)	−0.009 (2)	0.0003 (18)	−0.0041 (16)
C9	0.065 (2)	0.053 (2)	0.0449 (17)	−0.010 (2)	−0.0057 (17)	0.0051 (15)
C10	0.084 (3)	0.070 (3)	0.050 (2)	−0.010 (3)	−0.012 (2)	0.0120 (18)
C11	0.116 (4)	0.076 (3)	0.051 (2)	−0.022 (3)	−0.017 (3)	0.014 (2)
C12	0.111 (4)	0.071 (3)	0.050 (2)	−0.023 (3)	0.007 (2)	0.003 (2)
C13	0.081 (3)	0.063 (2)	0.057 (2)	−0.020 (2)	0.020 (2)	−0.0102 (19)
C14	0.150 (6)	0.158 (7)	0.114 (5)	−0.041 (6)	0.045 (5)	−0.027 (5)
C15	0.059 (2)	0.055 (2)	0.0533 (19)	−0.0064 (18)	0.0043 (17)	0.0035 (17)
C17	0.074 (3)	0.086 (3)	0.076 (3)	0.019 (3)	0.009 (3)	0.006 (3)

Geometric parameters (Å, º)

O16—C15	1.236 (3)	C11—C12	1.391 (8)
N1—C2	1.368 (5)	C12—C13	1.340 (6)
N1—C5	1.367 (4)	C13—C14	1.464 (7)
N1—H1	0.96 (4)	C15—C17	1.500 (6)
C2—C3	1.385 (3)	C3—H3	0.9300
C2—C15	1.444 (4)	C6—H6	0.9299
C3—C4	1.404 (5)	C7—H7	0.9304
C4—C9	1.441 (3)	C10—H10	0.9296
C4—C5	1.393 (4)	C11—H11	0.9307
C5—C6	1.409 (6)	C12—H12	0.9301
C6—C7	1.347 (5)	C14—H14A	0.9603
C7—C8	1.422 (5)	C14—H14B	0.9594
C8—C9	1.409 (6)	C14—H14C	0.9606
C8—C13	1.425 (5)	C17—H17A	0.9603
C9—C10	1.415 (5)	C17—H17B	0.9596
C10—C11	1.373 (5)	C17—H17C	0.9604
O16···N1	2.755 (4)	H3···C10	3.0981
O16···N1^i	2.894 (3)	H3···C17	2.9432
O16···H1	2.55 (5)	H3···H10	2.5895
O16···H1^i	1.99 (4)	H3···H17B	2.3163
O16···H17A^ii	2.6101	H6···C10^x	2.9470
O16···H11^iii	2.8814	H6···C11^x	2.8347
N1···O16	2.755 (4)	H6···C12^x	2.9138
N1···O16^ii	2.894 (3)	H6···C13^x	3.0811
C13···C17^iii	3.397 (7)	H7···C14	2.5462
C14···C17^iii	3.585 (10)	H7···H14A	2.2889
C17···C14^iv	3.585 (10)	H7···H14B	2.4114
C17···C13^iv	3.397 (7)	H10···C3	2.9282
C3···H17B	2.6956	H10···H3	2.5895
C3···H10	2.9282	H10···H14B^vii	2.4505
C6···H17B^v	3.0339	H11···O16^iv	2.8814
C7···H14B	2.8885	H12···H14C	2.2329
C7···H14A	2.7838	H12···C15^xi	3.0430
C10···H6^vi	2.9470	H12···H14C^viii	2.5053
C10···H14B^vii	2.8047	H14A···C7	2.7838
C10···H3	3.0981	H14A···H7	2.2889
C11···H6^vi	2.8347	H14A···C17^iii	3.0525
C12···H6^vi	2.9138	H14B···C7	2.8885
C12···H17C^iii	2.9003	H14B···C10^v	2.8047
C12···H14C^viii	2.8943	H14B···H7	2.4114
C13···H17C^iii	2.8296	H14B···H10^v	2.4505
C13···H6^vi	3.0811	H14C···H12	2.2329
C14···H7	2.5462	H14C···C12^xii	2.8943
C15···H12^ix	3.0430	H14C···H12^xii	2.5053
C15···H1^i	2.90 (4)	H17A···O16^i	2.6101
C17···H3	2.9432	H17B···C3	2.6956
C17···H14A^iv	3.0525	H17B···C6^vii	3.0339
H1···O16	2.55 (5)	H17B···H3	2.3163
H1···O16^ii	1.99 (4)	H17C···C12^iv	2.9003
H1···C15^ii	2.90 (4)	H17C···C13^iv	2.8296
C2—N1—C5	109.1 (2)	C2—C15—C17	118.6 (3)
C5—N1—H1	126 (3)	O16—C15—C2	119.9 (4)
C2—N1—H1	125 (3)	O16—C15—C17	121.6 (3)
N1—C2—C15	120.4 (2)	C2—C3—H3	126.41
N1—C2—C3	108.4 (3)	C4—C3—H3	126.41
C3—C2—C15	131.1 (4)	C5—C6—H6	121.42
C2—C3—C4	107.2 (3)	C7—C6—H6	121.41
C3—C4—C5	107.3 (2)	C6—C7—H7	118.47
C5—C4—C9	119.2 (3)	C8—C7—H7	118.39
C3—C4—C9	133.5 (3)	C9—C10—H10	120.51
N1—C5—C6	128.9 (3)	C11—C10—H10	120.56
N1—C5—C4	108.0 (3)	C10—C11—H11	119.47
C4—C5—C6	123.0 (2)	C12—C11—H11	119.45
C5—C6—C7	117.2 (3)	C11—C12—H12	119.45
C6—C7—C8	123.1 (4)	C13—C12—H12	119.51
C9—C8—C13	118.3 (3)	C13—C14—H14A	109.47
C7—C8—C13	121.6 (4)	C13—C14—H14B	109.52
C7—C8—C9	120.1 (3)	C13—C14—H14C	109.47
C4—C9—C10	122.7 (4)	H14A—C14—H14B	109.49
C4—C9—C8	117.3 (3)	H14A—C14—H14C	109.40
C8—C9—C10	120.0 (2)	H14B—C14—H14C	109.47
C9—C10—C11	118.9 (4)	C15—C17—H17A	109.47
C10—C11—C12	121.1 (4)	C15—C17—H17B	109.51
C11—C12—C13	121.0 (4)	C15—C17—H17C	109.46
C8—C13—C14	119.8 (4)	H17A—C17—H17B	109.49
C12—C13—C14	119.5 (4)	H17A—C17—H17C	109.42
C8—C13—C12	120.7 (4)	H17B—C17—H17C	109.47
C5—N1—C2—C3	1.2 (4)	C4—C5—C6—C7	1.1 (6)
C5—N1—C2—C15	179.7 (4)	N1—C5—C6—C7	−179.6 (4)
C2—N1—C5—C4	−1.4 (4)	C5—C6—C7—C8	−0.3 (6)
C2—N1—C5—C6	179.3 (4)	C6—C7—C8—C9	−0.3 (6)
C15—C2—C3—C4	−178.9 (4)	C6—C7—C8—C13	179.1 (4)
N1—C2—C15—O16	−2.6 (6)	C13—C8—C9—C10	0.1 (6)
N1—C2—C15—C17	177.0 (4)	C7—C8—C13—C14	1.4 (7)
N1—C2—C3—C4	−0.6 (4)	C9—C8—C13—C12	−0.9 (6)
C3—C2—C15—C17	−4.9 (7)	C7—C8—C13—C12	179.7 (4)
C3—C2—C15—O16	175.5 (4)	C7—C8—C9—C4	0.1 (5)
C2—C3—C4—C5	−0.2 (4)	C7—C8—C9—C10	179.5 (4)
C2—C3—C4—C9	−178.2 (4)	C13—C8—C9—C4	−179.3 (4)
C3—C4—C5—C6	−179.6 (4)	C9—C8—C13—C14	−179.3 (5)
C9—C4—C5—N1	179.3 (3)	C4—C9—C10—C11	179.9 (5)
C9—C4—C5—C6	−1.3 (6)	C8—C9—C10—C11	0.7 (6)
C3—C4—C9—C8	178.4 (4)	C9—C10—C11—C12	−0.5 (7)
C3—C4—C5—N1	0.9 (4)	C10—C11—C12—C13	−0.3 (8)
C3—C4—C9—C10	−0.9 (7)	C11—C12—C13—C8	1.1 (8)
C5—C4—C9—C8	0.6 (5)	C11—C12—C13—C14	179.4 (5)
C5—C4—C9—C10	−178.7 (4)

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) x+1, y, z; (vi) −x+2, y+1/2, −z+1/2; (vii) x−1, y, z; (viii) x−1/2, −y+1/2, −z; (ix) −x+3/2, −y+1, z+1/2; (x) −x+2, y−1/2, −z+1/2; (xi) −x+3/2, −y+1, z−1/2; (xii) x+1/2, −y+1/2, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O16^ii	0.96 (4)	1.99 (4)	2.894 (3)	156 (4)

Symmetry code: (ii) x+1/2, −y+1/2, −z+1.