tert-Butyl 3-(8-bromo-4H,10H-1,2-oxazolo[4,3-c][1]benzoxepin-10-yl)-2-methyl-1H-indole-1-carboxyl-ate.

In the title compound, C(25)H(23)BrN(2)O(4), the seven-membered ring adopts a twisted-boat conformation. The indole ring system is planar within 0.021 (2) Å and the ester group [-C(=O)-O-C-] is almost coplanar with it [dihedral angle = 3.0 (2)°]. The conformation of the ester group is influenced by intra-molecular C-H⋯O inter-actions. In the crystal structure, mol-ecules are linked into chains along the b axis by C-H⋯N hydrogen bonds.

Related literature

For general background to and biological applications of nitro­gen- and oxygen-containing heterocyclic compounds, see: Furstner (2003 ▶); Liddell (2002 ▶); Caramella & Grunanger (1984 ▶); Stormer et al. (2004 ▶); Erdelyi et al. (2008 ▶). Hou et al. (2003 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C25H23BrN2O4

M = 495.36

Monoclinic,

a = 16.0494 (6) Å

b = 9.6497 (4) Å

c = 16.2202 (7) Å

β = 116.267 (2)°

V = 2252.66 (16) Å3

Z = 4

Mo Kα radiation

μ = 1.86 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.982, T max = 0.982

20668 measured reflections

5584 independent reflections

2780 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.134

S = 1.00

5584 reflections

289 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027297/ci5101sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027297/ci5101Isup2.hkl

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

C25H23BrN2O4	F(000) = 1016
Mr = 495.36	Dx = 1.461 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1964 reflections
a = 16.0494 (6) Å	θ = 1.4–28.4°
b = 9.6497 (4) Å	µ = 1.86 mm−1
c = 16.2202 (7) Å	T = 293 K
β = 116.267 (2)°	Block, colourless
V = 2252.66 (16) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	5584 independent reflections
Radiation source: fine-focus sealed tube	2780 reflections with I > 2σ(I)
graphite	Rint = 0.049
ω and φ scans	θmax = 28.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −21→21
Tmin = 0.982, Tmax = 0.982	k = −12→12
20668 measured reflections	l = −21→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0504P)2 + 1.2404P] where P = (Fo2 + 2Fc2)/3
5584 reflections	(Δ/σ)max = 0.002
289 parameters	Δρmax = 0.40 e Å−3
1 restraint	Δρmin = −0.47 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.21016 (4)	0.94661 (4)	0.20807 (3)	0.0911 (2)
O1	0.48628 (16)	0.2154 (2)	0.14770 (17)	0.0662 (7)
O2	0.43563 (16)	0.6581 (2)	0.04692 (15)	0.0590 (6)
O3	−0.01565 (17)	0.2636 (3)	0.02194 (17)	0.0791 (8)
O4	0.02421 (14)	0.2088 (2)	0.16886 (14)	0.0513 (5)
N1	0.40074 (18)	0.2682 (3)	0.1374 (2)	0.0543 (7)
N2	0.12827 (16)	0.3153 (2)	0.13481 (16)	0.0389 (6)
C1	0.2807 (2)	0.8543 (3)	0.1577 (2)	0.0550 (8)
C2	0.2779 (2)	0.7113 (3)	0.1518 (2)	0.0476 (8)
H2	0.2406	0.6620	0.1719	0.057*
C3	0.3299 (2)	0.6404 (3)	0.1163 (2)	0.0424 (7)
C4	0.3153 (2)	0.4858 (3)	0.0952 (2)	0.0429 (7)
H4	0.2828	0.4793	0.0280	0.051*
C5	0.4033 (2)	0.4004 (3)	0.1233 (2)	0.0425 (7)
C6	0.5349 (2)	0.3220 (4)	0.1381 (2)	0.0584 (9)
H6	0.5940	0.3139	0.1411	0.070*
C7	0.4885 (2)	0.4401 (3)	0.1237 (2)	0.0462 (8)
C8	0.5156 (2)	0.5831 (4)	0.1103 (3)	0.0598 (9)
H8A	0.5432	0.6312	0.1689	0.072*
H8B	0.5615	0.5784	0.0868	0.072*
C9	0.3850 (2)	0.7190 (3)	0.0876 (2)	0.0468 (7)
C10	0.3868 (2)	0.8620 (4)	0.0935 (2)	0.0605 (9)
H10	0.4241	0.9122	0.0736	0.073*
C11	0.3343 (3)	0.9314 (3)	0.1283 (3)	0.0635 (10)
H11	0.3351	1.0276	0.1318	0.076*
C14	0.1088 (2)	0.3832 (4)	−0.0252 (2)	0.0559 (9)
H14A	0.0488	0.3422	−0.0430	0.084*
H14B	0.1407	0.3343	−0.0543	0.084*
H14C	0.1014	0.4786	−0.0439	0.084*
C12	0.2510 (2)	0.4182 (3)	0.1294 (2)	0.0404 (7)
C13	0.1637 (2)	0.3746 (3)	0.0763 (2)	0.0404 (7)
C15	0.19718 (19)	0.3240 (3)	0.2260 (2)	0.0376 (7)
C16	0.1986 (2)	0.2815 (3)	0.3088 (2)	0.0451 (7)
H16	0.1481	0.2360	0.3103	0.054*
C17	0.2775 (2)	0.3094 (4)	0.3884 (2)	0.0537 (8)
H17	0.2801	0.2820	0.4444	0.064*
C18	0.3536 (2)	0.3776 (4)	0.3872 (2)	0.0534 (8)
H18	0.4057	0.3961	0.4422	0.064*
C19	0.3518 (2)	0.4174 (3)	0.3050 (2)	0.0507 (8)
H19	0.4027	0.4623	0.3042	0.061*
C20	0.27401 (19)	0.3904 (3)	0.2236 (2)	0.0393 (7)
C21	0.0393 (2)	0.2605 (3)	0.1012 (2)	0.0476 (8)
C22	−0.0658 (2)	0.1391 (4)	0.1484 (2)	0.0542 (9)
C23	−0.0521 (3)	0.0973 (5)	0.2429 (3)	0.0806 (13)
H23A	−0.0023	0.0314	0.2682	0.121*
H23B	−0.1082	0.0562	0.2389	0.121*
H23C	−0.0371	0.1777	0.2817	0.121*
C24	−0.0771 (3)	0.0154 (4)	0.0874 (3)	0.0829 (12)
H24A	−0.0255	−0.0464	0.1173	0.124*
H24B	−0.0793	0.0459	0.0302	0.124*
H24C	−0.1338	−0.0320	0.0759	0.124*
C25	−0.1444 (2)	0.2408 (5)	0.1069 (3)	0.0769 (12)
H25A	−0.1527	0.2662	0.0466	0.115*
H25B	−0.1304	0.3220	0.1449	0.115*
H25C	−0.2005	0.1991	0.1028	0.115*

	U11	U22	U33	U12	U13	U23
Br1	0.1213 (4)	0.0499 (3)	0.1235 (4)	0.0187 (2)	0.0738 (3)	−0.0069 (2)
O1	0.0673 (15)	0.0465 (15)	0.0968 (19)	0.0139 (12)	0.0474 (14)	0.0101 (13)
O2	0.0687 (15)	0.0561 (15)	0.0683 (15)	−0.0004 (12)	0.0448 (13)	0.0146 (12)
O3	0.0632 (16)	0.114 (2)	0.0528 (16)	−0.0311 (15)	0.0189 (13)	0.0067 (15)
O4	0.0489 (12)	0.0553 (14)	0.0505 (12)	−0.0162 (11)	0.0227 (10)	0.0038 (10)
N1	0.0567 (16)	0.0364 (16)	0.082 (2)	0.0024 (13)	0.0422 (15)	0.0006 (14)
N2	0.0426 (13)	0.0335 (14)	0.0452 (14)	−0.0037 (11)	0.0237 (12)	0.0003 (11)
C1	0.062 (2)	0.0330 (19)	0.066 (2)	0.0045 (16)	0.0249 (18)	0.0017 (16)
C2	0.0547 (18)	0.0345 (18)	0.0562 (19)	−0.0033 (15)	0.0268 (16)	0.0012 (14)
C3	0.0484 (17)	0.0322 (17)	0.0484 (18)	−0.0027 (14)	0.0231 (15)	0.0042 (13)
C4	0.0460 (17)	0.0392 (18)	0.0475 (17)	−0.0070 (14)	0.0244 (15)	−0.0019 (14)
C5	0.0497 (18)	0.0348 (17)	0.0489 (18)	−0.0037 (14)	0.0272 (15)	−0.0040 (14)
C6	0.0510 (19)	0.060 (2)	0.071 (2)	0.0018 (18)	0.0331 (18)	0.0040 (18)
C7	0.0451 (17)	0.050 (2)	0.0492 (18)	−0.0044 (16)	0.0255 (15)	0.0002 (15)
C8	0.052 (2)	0.056 (2)	0.083 (2)	−0.0058 (17)	0.0392 (19)	0.0059 (19)
C9	0.0470 (17)	0.0425 (19)	0.0505 (18)	−0.0052 (15)	0.0212 (15)	0.0082 (15)
C10	0.062 (2)	0.043 (2)	0.077 (2)	−0.0082 (18)	0.0308 (19)	0.0171 (18)
C11	0.067 (2)	0.0293 (19)	0.084 (3)	−0.0055 (18)	0.024 (2)	0.0081 (17)
C14	0.063 (2)	0.059 (2)	0.051 (2)	−0.0106 (18)	0.0301 (17)	0.0022 (17)
C12	0.0488 (18)	0.0288 (16)	0.0482 (18)	0.0001 (13)	0.0257 (15)	0.0000 (13)
C13	0.0494 (17)	0.0288 (16)	0.0494 (18)	−0.0029 (14)	0.0279 (15)	0.0000 (13)
C15	0.0414 (16)	0.0247 (15)	0.0534 (19)	0.0016 (13)	0.0271 (15)	0.0002 (13)
C16	0.0476 (18)	0.0396 (18)	0.0522 (19)	0.0040 (14)	0.0259 (16)	0.0007 (15)
C17	0.061 (2)	0.053 (2)	0.052 (2)	0.0126 (18)	0.0289 (18)	0.0041 (16)
C18	0.0466 (18)	0.053 (2)	0.0486 (19)	0.0052 (16)	0.0106 (15)	−0.0094 (16)
C19	0.0513 (19)	0.048 (2)	0.052 (2)	0.0023 (16)	0.0223 (17)	−0.0009 (15)
C20	0.0404 (16)	0.0293 (15)	0.0478 (18)	0.0009 (13)	0.0191 (14)	−0.0047 (13)
C21	0.0484 (19)	0.045 (2)	0.049 (2)	−0.0041 (15)	0.0211 (17)	−0.0001 (15)
C22	0.0475 (19)	0.054 (2)	0.060 (2)	−0.0169 (17)	0.0229 (16)	0.0019 (17)
C23	0.072 (2)	0.095 (3)	0.072 (2)	−0.031 (2)	0.030 (2)	0.018 (2)
C24	0.090 (3)	0.061 (3)	0.105 (3)	−0.032 (2)	0.050 (3)	−0.020 (2)
C25	0.053 (2)	0.090 (3)	0.087 (3)	−0.004 (2)	0.031 (2)	0.005 (2)

Br1—C1	1.887 (3)	C11—H11	0.93
O1—C6	1.342 (4)	C14—C13	1.487 (4)
O1—N1	1.403 (3)	C14—H14A	0.96
O2—C9	1.384 (4)	C14—H14B	0.96
O2—C8	1.436 (4)	C14—H14C	0.96
O3—C21	1.195 (4)	C12—C13	1.347 (4)
O4—C21	1.321 (4)	C12—C20	1.429 (4)
O4—C22	1.492 (3)	C15—C16	1.396 (4)
N1—C5	1.300 (4)	C15—C20	1.405 (4)
N2—C21	1.388 (4)	C16—C17	1.376 (4)
N2—C15	1.403 (4)	C16—H16	0.93
N2—C13	1.425 (3)	C17—C18	1.396 (5)
C1—C11	1.372 (5)	C17—H17	0.93
C1—C2	1.382 (4)	C18—C19	1.376 (4)
C2—C3	1.386 (4)	C18—H18	0.93
C2—H2	0.93	C19—C20	1.383 (4)
C3—C9	1.392 (4)	C19—H19	0.93
C3—C4	1.525 (4)	C22—C25	1.502 (5)
C4—C12	1.518 (4)	C22—C23	1.503 (5)
C4—C5	1.520 (4)	C22—C24	1.509 (5)
C4—H4	0.98	C23—H23A	0.96
C5—C7	1.417 (4)	C23—H23B	0.96
C6—C7	1.325 (5)	C23—H23C	0.96
C6—H6	0.93	C24—H24A	0.96
C7—C8	1.491 (4)	C24—H24B	0.96
C8—H8A	0.97	C24—H24C	0.96
C8—H8B	0.97	C25—H25A	0.96
C9—C10	1.383 (5)	C25—H25B	0.96
C10—C11	1.378 (5)	C25—H25C	0.96
C10—H10	0.93
C6—O1—N1	107.3 (2)	C13—C12—C20	109.2 (2)
C9—O2—C8	113.6 (2)	C13—C12—C4	125.7 (3)
C21—O4—C22	120.0 (2)	C20—C12—C4	125.1 (3)
C5—N1—O1	105.8 (2)	C12—C13—N2	108.0 (2)
C21—N2—C15	129.1 (2)	C12—C13—C14	129.0 (3)
C21—N2—C13	122.4 (2)	N2—C13—C14	123.0 (3)
C15—N2—C13	108.5 (2)	C16—C15—N2	131.8 (3)
C11—C1—C2	121.5 (3)	C16—C15—C20	121.4 (3)
C11—C1—Br1	118.9 (3)	N2—C15—C20	106.9 (2)
C2—C1—Br1	119.6 (3)	C17—C16—C15	117.4 (3)
C1—C2—C3	121.0 (3)	C17—C16—H16	121.3
C1—C2—H2	119.5	C15—C16—H16	121.3
C3—C2—H2	119.5	C16—C17—C18	121.9 (3)
C2—C3—C9	117.2 (3)	C16—C17—H17	119.1
C2—C3—C4	121.0 (3)	C18—C17—H17	119.1
C9—C3—C4	121.0 (3)	C19—C18—C17	120.1 (3)
C12—C4—C5	110.4 (2)	C19—C18—H18	119.9
C12—C4—C3	113.6 (2)	C17—C18—H18	119.9
C5—C4—C3	115.6 (2)	C18—C19—C20	119.7 (3)
C12—C4—H4	105.4	C18—C19—H19	120.1
C5—C4—H4	105.4	C20—C19—H19	120.1
C3—C4—H4	105.4	C19—C20—C15	119.5 (3)
N1—C5—C7	111.7 (3)	C19—C20—C12	133.0 (3)
N1—C5—C4	119.2 (3)	C15—C20—C12	107.5 (2)
C7—C5—C4	128.4 (3)	O3—C21—O4	125.7 (3)
C7—C6—O1	111.7 (3)	O3—C21—N2	123.6 (3)
C7—C6—H6	124.2	O4—C21—N2	110.6 (3)
O1—C6—H6	124.2	O4—C22—C25	110.1 (3)
C6—C7—C5	103.6 (3)	O4—C22—C23	101.8 (3)
C6—C7—C8	130.1 (3)	C25—C22—C23	110.3 (3)
C5—C7—C8	126.3 (3)	O4—C22—C24	109.1 (3)
O2—C8—C7	110.2 (3)	C25—C22—C24	112.9 (3)
O2—C8—H8A	109.6	C23—C22—C24	112.1 (3)
C7—C8—H8A	109.6	C22—C23—H23A	109.5
O2—C8—H8B	109.6	C22—C23—H23B	109.5
C7—C8—H8B	109.6	H23A—C23—H23B	109.5
H8A—C8—H8B	108.1	C22—C23—H23C	109.5
C10—C9—O2	117.2 (3)	H23A—C23—H23C	109.5
C10—C9—C3	121.2 (3)	H23B—C23—H23C	109.5
O2—C9—C3	121.5 (3)	C22—C24—H24A	109.5
C11—C10—C9	121.0 (3)	C22—C24—H24B	109.5
C11—C10—H10	119.5	H24A—C24—H24B	109.5
C9—C10—H10	119.5	C22—C24—H24C	109.5
C1—C11—C10	118.1 (3)	H24A—C24—H24C	109.5
C1—C11—H11	121.0	H24B—C24—H24C	109.5
C10—C11—H11	121.0	C22—C25—H25A	109.5
C13—C14—H14A	109.5	C22—C25—H25B	109.5
C13—C14—H14B	109.5	H25A—C25—H25B	109.5
H14A—C14—H14B	109.5	C22—C25—H25C	109.5
C13—C14—H14C	109.5	H25A—C25—H25C	109.5
H14A—C14—H14C	109.5	H25B—C25—H25C	109.5
H14B—C14—H14C	109.5
C6—O1—N1—C5	−0.5 (3)	C5—C4—C12—C20	59.5 (4)
C11—C1—C2—C3	0.4 (5)	C3—C4—C12—C20	−72.3 (4)
Br1—C1—C2—C3	−179.1 (2)	C20—C12—C13—N2	−0.9 (3)
C1—C2—C3—C9	0.4 (5)	C4—C12—C13—N2	179.0 (3)
C1—C2—C3—C4	−169.9 (3)	C20—C12—C13—C14	178.9 (3)
C2—C3—C4—C12	−8.4 (4)	C4—C12—C13—C14	−1.3 (5)
C9—C3—C4—C12	−178.3 (3)	C21—N2—C13—C12	179.9 (3)
C2—C3—C4—C5	−137.6 (3)	C15—N2—C13—C12	0.0 (3)
C9—C3—C4—C5	52.5 (4)	C21—N2—C13—C14	0.1 (4)
O1—N1—C5—C7	0.0 (3)	C15—N2—C13—C14	−179.8 (3)
O1—N1—C5—C4	171.0 (2)	C21—N2—C15—C16	0.4 (5)
C12—C4—C5—N1	26.0 (4)	C13—N2—C15—C16	−179.7 (3)
C3—C4—C5—N1	156.7 (3)	C21—N2—C15—C20	−179.0 (3)
C12—C4—C5—C7	−164.6 (3)	C13—N2—C15—C20	0.9 (3)
C3—C4—C5—C7	−33.9 (4)	N2—C15—C16—C17	−178.1 (3)
N1—O1—C6—C7	1.0 (4)	C20—C15—C16—C17	1.2 (4)
O1—C6—C7—C5	−0.9 (4)	C15—C16—C17—C18	0.0 (5)
O1—C6—C7—C8	179.3 (3)	C16—C17—C18—C19	−0.9 (5)
N1—C5—C7—C6	0.6 (4)	C17—C18—C19—C20	0.4 (5)
C4—C5—C7—C6	−169.4 (3)	C18—C19—C20—C15	0.8 (4)
N1—C5—C7—C8	−179.7 (3)	C18—C19—C20—C12	179.8 (3)
C4—C5—C7—C8	10.3 (5)	C16—C15—C20—C19	−1.7 (4)
C9—O2—C8—C7	84.3 (3)	N2—C15—C20—C19	177.8 (3)
C6—C7—C8—O2	145.6 (3)	C16—C15—C20—C12	179.1 (3)
C5—C7—C8—O2	−34.0 (4)	N2—C15—C20—C12	−1.4 (3)
C8—O2—C9—C10	110.5 (3)	C13—C12—C20—C19	−177.6 (3)
C8—O2—C9—C3	−73.3 (4)	C4—C12—C20—C19	2.6 (5)
C2—C3—C9—C10	−0.7 (5)	C13—C12—C20—C15	1.4 (3)
C4—C3—C9—C10	169.6 (3)	C4—C12—C20—C15	−178.4 (3)
C2—C3—C9—O2	−176.7 (3)	C22—O4—C21—O3	4.0 (5)
C4—C3—C9—O2	−6.3 (4)	C22—O4—C21—N2	−177.5 (2)
O2—C9—C10—C11	176.4 (3)	C15—N2—C21—O3	176.7 (3)
C3—C9—C10—C11	0.2 (5)	C13—N2—C21—O3	−3.2 (5)
C2—C1—C11—C10	−0.8 (5)	C15—N2—C21—O4	−1.8 (4)
Br1—C1—C11—C10	178.7 (3)	C13—N2—C21—O4	178.3 (2)
C9—C10—C11—C1	0.5 (5)	C21—O4—C22—C25	−63.4 (4)
C5—C4—C12—C13	−120.3 (3)	C21—O4—C22—C23	179.7 (3)
C3—C4—C12—C13	107.9 (3)	C21—O4—C22—C24	61.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···O3	0.96	1.93	2.694 (4)	135
C24—H24B···O3	0.96	2.37	2.961 (5)	120
C11—H11···N1i	0.93	2.53	3.404 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯O3	0.96	1.93	2.694 (4)	135
C24—H24B⋯O3	0.96	2.37	2.961 (5)	120
C11—H11⋯N1i	0.93	2.53	3.404 (4)	156

Symmetry code: (i) .