5-p-Tolyl-1,2,3,3a-tetra-hydro-benzo[e]pyrrolo-[2,1-b][1,3]oxazepin-10(5H)-one.

The structure of the title compound, C(19)H(19)NO(2), contains a seven-membered ring, which is fused to one five- and one six-membered ring, and carries a tolyl substituent. The two benzene rings are oriented relative to each other at a dihedral angle of 86.90 (7)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background to asymmetric photochemical reactions, see: Gould et al. (2001 ▶); Grätzel (2001 ▶); Korzeniewski & Zoladz (2001 ▶); Aubert et al. (2000 ▶). For related structures, see: Basarić et al. (2008 ▶); Griesbeck et al. (1997 ▶, 1999 ▶, 2002 ▶).

Experimental

Crystal data

C19H19NO2

M = 293.35

Monoclinic,

a = 8.237 (3) Å

b = 16.868 (6) Å

c = 11.267 (4) Å

β = 100.851 (6)°

V = 1537.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.20 × 0.18 × 0.17 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996 ▶) T min = 0.736, T max = 1.000

13060 measured reflections

3501 independent reflections

2338 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.188

S = 1.01

3501 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2004 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811020964/ez2247sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020964/ez2247Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020964/ez2247Isup3.cml

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

C19H19NO2	F(000) = 624
Mr = 293.35	Dx = 1.267 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4317 reflections
a = 8.237 (3) Å	θ = 2.2–27.5°
b = 16.868 (6) Å	µ = 0.08 mm−1
c = 11.267 (4) Å	T = 296 K
β = 100.851 (6)°	Prism, colourless
V = 1537.6 (10) Å3	0.20 × 0.18 × 0.17 mm
Z = 4

Bruker APEXII area-detector diffractometer	3501 independent reflections
Radiation source: fine-focus sealed tube	2338 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.736, Tmax = 1.000	k = −21→21
13060 measured reflections	l = −12→14

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.188	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.105P)2] where P = (Fo2 + 2Fc2)/3
3501 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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	0.15809 (16)	0.47030 (7)	0.33133 (12)	0.0557 (4)
N1	0.00869 (19)	0.40627 (9)	0.15419 (14)	0.0512 (4)
C1	0.2534 (3)	0.33184 (14)	0.1825 (2)	0.0753 (7)
H1A	0.2936	0.2797	0.1659	0.113*
H1B	0.3427	0.3699	0.1866	0.113*
O2	−0.18305 (19)	0.44457 (9)	−0.00756 (13)	0.0663 (4)
C2	0.1855 (3)	0.33170 (12)	0.2983 (2)	0.0704 (6)
H2A	0.2735	0.3382	0.3681	0.106*
H2B	0.1272	0.2827	0.3069	0.106*
C3	0.1049 (3)	0.35569 (13)	0.0862 (2)	0.0673 (6)
H3A	0.1393	0.3849	0.0210	0.101*
H3B	0.0417	0.3096	0.0531	0.101*
C4	−0.3496 (3)	0.58920 (13)	0.3392 (2)	0.0637 (6)
H4A	−0.3995	0.6193	0.3914	0.096*
C5	0.4603 (3)	0.79714 (14)	0.5623 (2)	0.0754 (7)
H5A	0.4984	0.7799	0.6440	0.113*
H5B	0.3937	0.8438	0.5622	0.113*
H5C	0.5535	0.8089	0.5255	0.113*
C6	−0.3713 (2)	0.50009 (12)	0.17358 (19)	0.0583 (5)
H6A	−0.4362	0.4709	0.1124	0.087*
C7	−0.4450 (3)	0.54405 (13)	0.2524 (2)	0.0664 (6)
H7A	−0.5592	0.5429	0.2463	0.100*
C8	0.2897 (3)	0.74206 (12)	0.3717 (2)	0.0595 (5)
H8A	0.3033	0.7900	0.3341	0.089*
C9	0.2009 (2)	0.68221 (12)	0.30601 (19)	0.0558 (5)
H9A	0.1555	0.6906	0.2250	0.084*
C10	−0.1795 (2)	0.59058 (11)	0.35038 (18)	0.0536 (5)
H10A	−0.1167	0.6224	0.4092	0.080*
C11	0.3356 (3)	0.66015 (12)	0.54475 (18)	0.0589 (5)
H11A	0.3809	0.6522	0.6259	0.088*
C12	−0.2000 (2)	0.49935 (11)	0.18561 (16)	0.0470 (4)
C13	0.0680 (2)	0.40196 (11)	0.28510 (17)	0.0529 (5)
H13A	−0.0237	0.3922	0.3274	0.079*
C14	0.3585 (2)	0.73232 (11)	0.49200 (19)	0.0545 (5)
C15	0.2468 (3)	0.59949 (12)	0.47968 (18)	0.0578 (5)
H15A	0.2331	0.5516	0.5175	0.087*
C16	0.1782 (2)	0.60969 (11)	0.35837 (16)	0.0463 (4)
C17	0.0854 (2)	0.54463 (10)	0.28326 (16)	0.0463 (4)
H17A	0.1067	0.5501	0.2010	0.069*
C18	−0.1249 (2)	0.44804 (11)	0.10158 (17)	0.0505 (5)
C19	−0.1014 (2)	0.54521 (10)	0.27503 (16)	0.0442 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0487 (8)	0.0543 (8)	0.0601 (9)	0.0093 (6)	0.0006 (6)	−0.0076 (6)
N1	0.0479 (9)	0.0542 (8)	0.0526 (9)	0.0007 (7)	0.0119 (7)	−0.0068 (7)
C1	0.0647 (14)	0.0654 (13)	0.0979 (19)	0.0143 (11)	0.0205 (13)	−0.0125 (12)
O2	0.0627 (9)	0.0857 (11)	0.0481 (8)	−0.0147 (8)	0.0046 (7)	−0.0054 (7)
C2	0.0688 (14)	0.0576 (12)	0.0835 (16)	0.0105 (10)	0.0109 (12)	−0.0003 (11)
C3	0.0717 (14)	0.0625 (12)	0.0727 (15)	−0.0003 (11)	0.0265 (12)	−0.0188 (11)
C4	0.0536 (12)	0.0651 (12)	0.0772 (15)	0.0140 (10)	0.0246 (11)	0.0023 (11)
C5	0.0737 (15)	0.0639 (13)	0.0851 (17)	−0.0010 (11)	0.0055 (13)	−0.0114 (12)
C6	0.0408 (10)	0.0650 (12)	0.0670 (13)	0.0005 (9)	0.0045 (9)	0.0064 (10)
C7	0.0422 (11)	0.0737 (13)	0.0854 (16)	0.0109 (10)	0.0174 (11)	0.0113 (12)
C8	0.0570 (12)	0.0510 (10)	0.0686 (13)	0.0036 (9)	0.0069 (10)	0.0019 (10)
C9	0.0494 (11)	0.0588 (11)	0.0575 (12)	0.0071 (9)	0.0054 (9)	0.0025 (9)
C10	0.0522 (11)	0.0548 (10)	0.0559 (11)	0.0085 (9)	0.0160 (9)	0.0002 (9)
C11	0.0619 (12)	0.0656 (12)	0.0471 (11)	−0.0049 (10)	0.0046 (9)	−0.0045 (9)
C12	0.0418 (10)	0.0519 (10)	0.0479 (10)	−0.0003 (8)	0.0098 (8)	0.0075 (8)
C13	0.0516 (11)	0.0514 (10)	0.0552 (12)	0.0021 (8)	0.0090 (9)	−0.0013 (9)
C14	0.0481 (11)	0.0514 (10)	0.0636 (13)	0.0026 (8)	0.0097 (9)	−0.0107 (9)
C15	0.0651 (13)	0.0597 (11)	0.0494 (11)	−0.0083 (10)	0.0125 (9)	−0.0011 (9)
C16	0.0381 (9)	0.0540 (10)	0.0486 (10)	0.0015 (7)	0.0126 (8)	−0.0054 (8)
C17	0.0421 (10)	0.0535 (10)	0.0444 (10)	0.0013 (8)	0.0112 (8)	−0.0024 (8)
C18	0.0456 (10)	0.0557 (10)	0.0508 (11)	−0.0116 (8)	0.0103 (8)	−0.0006 (9)
C19	0.0395 (9)	0.0494 (9)	0.0443 (10)	0.0025 (7)	0.0099 (7)	0.0055 (8)

O1—C13	1.416 (2)	C6—C7	1.382 (3)
O1—C17	1.450 (2)	C6—C12	1.391 (3)
N1—C18	1.347 (2)	C6—H6A	0.9300
N1—C13	1.466 (2)	C7—H7A	0.9300
N1—C3	1.474 (2)	C8—C14	1.377 (3)
C1—C2	1.514 (4)	C8—C9	1.378 (3)
C1—C3	1.528 (3)	C8—H8A	0.9300
C1—H1A	0.9700	C9—C16	1.386 (3)
C1—H1B	0.9700	C9—H9A	0.9300
O2—C18	1.234 (2)	C10—C19	1.388 (3)
C2—C13	1.520 (3)	C10—H10A	0.9300
C2—H2A	0.9700	C11—C14	1.383 (3)
C2—H2B	0.9700	C11—C15	1.385 (3)
C3—H3A	0.9700	C11—H11A	0.9300
C3—H3B	0.9700	C12—C19	1.402 (3)
C4—C7	1.366 (3)	C12—C18	1.500 (3)
C4—C10	1.383 (3)	C13—H13A	0.9800
C4—H4A	0.9300	C15—C16	1.388 (3)
C5—C14	1.509 (3)	C15—H15A	0.9300
C5—H5A	0.9600	C16—C17	1.504 (2)
C5—H5B	0.9600	C17—C19	1.524 (2)
C5—H5C	0.9600	C17—H17A	0.9800
C13—O1—C17	114.55 (13)	C8—C9—C16	121.24 (19)
C18—N1—C13	123.97 (15)	C8—C9—H9A	119.4
C18—N1—C3	123.30 (17)	C16—C9—H9A	119.4
C13—N1—C3	112.62 (16)	C4—C10—C19	120.91 (19)
C2—C1—C3	103.64 (19)	C4—C10—H10A	119.5
C2—C1—H1A	111.0	C19—C10—H10A	119.5
C3—C1—H1A	111.0	C14—C11—C15	121.61 (19)
C2—C1—H1B	111.0	C14—C11—H11A	119.2
C3—C1—H1B	111.0	C15—C11—H11A	119.2
H1A—C1—H1B	109.0	C6—C12—C19	120.33 (18)
C1—C2—C13	104.25 (19)	C6—C12—C18	118.34 (17)
C1—C2—H2A	110.9	C19—C12—C18	121.32 (16)
C13—C2—H2A	110.9	O1—C13—N1	112.46 (15)
C1—C2—H2B	110.9	O1—C13—C2	108.58 (16)
C13—C2—H2B	110.9	N1—C13—C2	102.88 (16)
H2A—C2—H2B	108.9	O1—C13—H13A	110.9
N1—C3—C1	102.74 (16)	N1—C13—H13A	110.9
N1—C3—H3A	111.2	C2—C13—H13A	110.9
C1—C3—H3A	111.2	C8—C14—C11	117.62 (18)
N1—C3—H3B	111.2	C8—C14—C5	121.05 (19)
C1—C3—H3B	111.2	C11—C14—C5	121.30 (19)
H3A—C3—H3B	109.1	C11—C15—C16	120.43 (18)
C7—C4—C10	120.74 (19)	C11—C15—H15A	119.8
C7—C4—H4A	119.6	C16—C15—H15A	119.8
C10—C4—H4A	119.6	C9—C16—C15	117.76 (17)
C14—C5—H5A	109.5	C9—C16—C17	119.98 (17)
C14—C5—H5B	109.5	C15—C16—C17	122.24 (16)
H5A—C5—H5B	109.5	O1—C17—C16	106.89 (14)
C14—C5—H5C	109.5	O1—C17—C19	111.69 (14)
H5A—C5—H5C	109.5	C16—C17—C19	115.45 (14)
H5B—C5—H5C	109.5	O1—C17—H17A	107.5
C7—C6—C12	120.2 (2)	C16—C17—H17A	107.5
C7—C6—H6A	119.9	C19—C17—H17A	107.5
C12—C6—H6A	119.9	O2—C18—N1	123.04 (18)
C4—C7—C6	119.7 (2)	O2—C18—C12	121.86 (18)
C4—C7—H7A	120.1	N1—C18—C12	115.10 (16)
C6—C7—H7A	120.1	C10—C19—C12	118.08 (17)
C14—C8—C9	121.34 (19)	C10—C19—C17	123.07 (17)
C14—C8—H8A	119.3	C12—C19—C17	118.83 (16)
C9—C8—H8A	119.3

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O2i	0.96	2.42	3.354 (3)	163.
C17—H17A···O2ii	0.98	2.38	3.357 (3)	174.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O2i	0.96	2.42	3.354 (3)	163
C17—H17A⋯O2ii	0.98	2.38	3.357 (3)	174

Symmetry codes: (i) ; (ii) .