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

Jin, Y.-Z.; Liu, C.-E.; Zhang, R.-H.; Fu, D.-X.; Lv, Y.-K.

doi:10.1107/S1600536811020964

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1593

doi:10.1107/S1600536811020964

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

Yun-Zhou Jin,^a Cai-E Liu,^a Rong-Hua Zhang,^a ^* Da-Xu Fu ^a and Yao-Kang Lv ^a

^aChemistry Department, Tongji University, Shanghai 200092, People's Republic of China
^*Correspondence e-mail: tj_zrh@163.com

(Received 11 May 2011; accepted 31 May 2011; online 11 June 2011)

The structure of the title compound, C₁₉H₁₉NO₂, 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, molecules are linked by weak intermolecular 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_r = 293.35
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.188
S = 1.01
3501 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020964/ez2247sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811020964/ez2247Isup3.cml

checkCIF report

Comment top

Asymmetric photochemistry is one of the most important reactions in organic chemistry. Many compounds can be obtained in one step, but can not be synthesized in the ground state (Gould et al.,2001; Grätzel, 2001; Korzeniewski & Zoladz, 2001; Aubert et al., 2000). Benzophenone acylamide derivatives can form a seven-membered ring with high stereoselectivity through intramolecular photoinduced decarboxylation and cyclization (Basarić et al., 2008; Griesbeck et al., 1997; Griesbeck et al., 1999; Griesbeck et al., 2002). We report herein the crystal structure and synthesis of the title compound.

The structure of the title compound which contains a seven-membered ring, a five-membered ring and two six-membered rings is shown in Fig. 1. The dihedral angle between the two benzene rings is 86.90 (7)°. Atoms C13 and C17 of the title compound are chiral centers. There are weak C—H···O hydrogen bonds which link neighboring molecules to form a two-dimensional layer in the bc plane (Fig. 2).

Related literature top

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 top

The title compound was the main product from the photoreaction of (S)-1-(2-(4-methylbenzoyl) benzoyl)pyrrolidine-2-carboxylic acid under N₂ for 10 h. The compound was purified by flash column chromatography (silica gel column, petroleum ether/ethyl acetate=3/1). Colorless crystals for the X-ray crystallographic studies were gained from slow evaporation of a dichloromethane solution.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atomic numbering scheme.
	Fig. 2. Partial packing view showing the C—H···O interactions and the formation of two-dimensional layer in the bc plane.

5-p-Tolyl-1,2,3,3a-tetrahydrobenzo[e]pyrrolo[2,1- b][1,3]oxazepin-10(5H)-one top

Crystal data top

C₁₉H₁₉NO₂	F(000) = 624
M_r = 293.35	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.105P)²] where P = (F_o² + 2F_c²)/3
3501 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₉NO₂	V = 1537.6 (10) Å³
M_r = 293.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.237 (3) Å	µ = 0.08 mm⁻¹
b = 16.868 (6) Å	T = 296 K
c = 11.267 (4) Å	0.20 × 0.18 × 0.17 mm
β = 100.851 (6)°

Data collection top

Bruker APEXII area-detector diffractometer	3501 independent reflections
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	2338 reflections with I > 2σ(I)
T_min = 0.736, T_max = 1.000	R_int = 0.030
13060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.188	H-atom parameters constrained
S = 1.01	Δρ_max = 0.46 e Å⁻³
3501 reflections	Δρ_min = −0.22 e Å⁻³
199 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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉NO₂
M_r	293.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.237 (3), 16.868 (6), 11.267 (4)
β (°)	100.851 (6)
V (Å³)	1537.6 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.17

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Empirical (using intensity measurements) (SADABS; Sheldrick, 1996)
T_min, T_max	0.736, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13060, 3501, 2338
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.188, 1.01
No. of reflections	3501
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.22

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O2ⁱ	0.96	2.42	3.354 (3)	163.2
C17—H17A···O2ⁱⁱ	0.98	2.38	3.357 (3)	174.1

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z.

Acknowledgements

Financial support from the National Natural Science Foundation of China is gratefully acknowledged.

References

Aubert, C., Vos, M. H., Mathis, P., Eker, A. P. M. & Brettel, K. (2000). Nature (London), 405, 586–590. Web of Science PubMed CAS Google Scholar
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