3'-(3-Hy-droxy-phen-yl)-4-methyl-spiro-[benzo[e][1,4]diazepine-3,2'-oxirane]-2,5(1H,4H)-dione.

In the title compound, C(17)H(14)N(2)O(4), the seven-membered ring adopts a boat conformation, and the two benzene rings make a dihedral angle of 45.22 (5)°. The crystal packing is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the biological activity of the title compound, see: Birkinshaw et al. (1963 ▶); Cutler et al. (1984 ▶); Heguy, et al. (1998 ▶). For the biosynthesis of cyclo­penol, see: Nover & Luckner (1969 ▶).

Experimental

Crystal data

C17H14N2O4

M = 310.30

Monoclinic,

a = 7.0066 (2) Å

b = 11.6160 (4) Å

c = 9.1568 (2) Å

β = 108.157 (1)°

V = 708.15 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 193 K

0.55 × 0.32 × 0.22 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

6890 measured reflections

1701 independent reflections

1627 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.107

S = 0.99

1701 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811022161/xu5236sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022161/xu5236Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022161/xu5236Isup3.cml

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

C17H14N2O4	F(000) = 324
Mr = 310.30	Dx = 1.455 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1484 reflections
a = 7.0066 (2) Å	θ = 1.9–27.5°
b = 11.6160 (4) Å	µ = 0.11 mm−1
c = 9.1568 (2) Å	T = 193 K
β = 108.157 (1)°	Block, colourless
V = 708.15 (4) Å3	0.55 × 0.32 × 0.22 mm
Z = 2

Bruker SMART 1000 CCD area-detector diffractometer	1627 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 27.5°, θmin = 3.1°
φ and ω scans	h = −8→9
6890 measured reflections	k = −15→15
1701 independent reflections	l = −11→11

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
1701 reflections	(Δ/σ)max = 0.009
208 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.24 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
O2	0.4377 (2)	0.08072 (14)	0.31423 (17)	0.0269 (3)
O3	0.4521 (2)	0.40192 (14)	0.02123 (17)	0.0227 (3)
O1	0.6694 (2)	0.51497 (15)	0.29249 (19)	0.0291 (4)
O4	−0.0361 (2)	0.06229 (14)	−0.25108 (18)	0.0271 (4)
H4A	0.0758	0.0542	−0.2604	0.041*
N2	0.4837 (2)	0.24388 (15)	0.19567 (18)	0.0184 (3)
N1	0.4887 (2)	0.42631 (15)	0.42617 (18)	0.0205 (4)
H1	0.5578	0.4610	0.5087	0.025*
C8	0.3244 (3)	0.35791 (17)	0.4353 (2)	0.0186 (4)
C9	0.2804 (3)	0.24831 (18)	0.3691 (2)	0.0186 (4)
C7	0.2100 (3)	0.40240 (19)	0.5227 (2)	0.0216 (4)
H7	0.2433	0.4733	0.5712	0.026*
C4	0.1162 (3)	0.18798 (19)	0.3878 (2)	0.0236 (4)
H4	0.0858	0.1152	0.3445	0.028*
C3	0.4063 (3)	0.18510 (18)	0.2913 (2)	0.0192 (4)
C12	0.1144 (3)	0.22949 (19)	−0.1034 (2)	0.0212 (4)
H12	0.2423	0.1976	−0.0787	0.025*
C10	0.6209 (3)	0.1863 (2)	0.1253 (2)	0.0257 (4)
H10A	0.6350	0.1068	0.1554	0.038*
H10B	0.7499	0.2231	0.1592	0.038*
H10C	0.5671	0.1915	0.0154	0.038*
C16	−0.1031 (3)	0.3876 (2)	−0.0884 (2)	0.0241 (4)
H16	−0.1207	0.4607	−0.0531	0.029*
C11	0.0875 (3)	0.33865 (18)	−0.0492 (2)	0.0201 (4)
C14	−0.2433 (3)	0.21769 (19)	−0.2334 (2)	0.0234 (4)
H14	−0.3541	0.1771	−0.2941	0.028*
C6	0.0469 (3)	0.3415 (2)	0.5378 (2)	0.0247 (4)
H6	−0.0307	0.3725	0.5941	0.030*
C13	−0.0508 (3)	0.16860 (19)	−0.1948 (2)	0.0208 (4)
C17	0.2579 (3)	0.40891 (18)	0.0485 (2)	0.0198 (4)
H17	0.2200	0.4869	0.0695	0.024*
C15	−0.2672 (3)	0.3264 (2)	−0.1808 (2)	0.0252 (4)
H15	−0.3946	0.3592	−0.2075	0.030*
C2	0.4422 (3)	0.36451 (16)	0.1645 (2)	0.0180 (4)
C5	−0.0007 (3)	0.2341 (2)	0.4688 (2)	0.0267 (5)
H5	−0.1113	0.1937	0.4774	0.032*
C1	0.5463 (3)	0.44186 (18)	0.2995 (2)	0.0195 (4)

	U11	U22	U33	U12	U13	U23
O2	0.0382 (8)	0.0157 (7)	0.0268 (7)	0.0038 (6)	0.0100 (6)	0.0041 (6)
O3	0.0288 (7)	0.0214 (7)	0.0222 (7)	0.0002 (5)	0.0139 (5)	0.0024 (6)
O1	0.0309 (8)	0.0236 (8)	0.0359 (8)	−0.0097 (6)	0.0149 (6)	−0.0027 (7)
O4	0.0268 (7)	0.0222 (8)	0.0341 (8)	−0.0028 (6)	0.0121 (6)	−0.0060 (6)
N2	0.0227 (7)	0.0155 (8)	0.0180 (7)	0.0029 (6)	0.0077 (6)	0.0006 (7)
N1	0.0236 (8)	0.0174 (8)	0.0189 (8)	−0.0052 (6)	0.0044 (6)	−0.0034 (6)
C8	0.0194 (9)	0.0184 (9)	0.0169 (8)	−0.0022 (7)	0.0042 (7)	0.0015 (7)
C9	0.0225 (8)	0.0181 (9)	0.0144 (8)	0.0006 (7)	0.0046 (7)	0.0022 (7)
C7	0.0273 (9)	0.0183 (9)	0.0180 (8)	0.0001 (7)	0.0052 (7)	−0.0012 (7)
C4	0.0251 (9)	0.0204 (10)	0.0234 (9)	−0.0063 (8)	0.0050 (7)	0.0004 (8)
C3	0.0220 (9)	0.0140 (9)	0.0188 (8)	0.0025 (7)	0.0021 (6)	0.0016 (7)
C12	0.0234 (9)	0.0216 (10)	0.0186 (8)	0.0041 (7)	0.0065 (7)	0.0022 (7)
C10	0.0248 (10)	0.0251 (11)	0.0290 (9)	0.0094 (8)	0.0113 (7)	−0.0007 (8)
C16	0.0289 (10)	0.0229 (10)	0.0216 (9)	0.0058 (8)	0.0096 (8)	0.0013 (8)
C11	0.0256 (9)	0.0208 (10)	0.0149 (8)	0.0012 (7)	0.0076 (7)	0.0007 (7)
C14	0.0204 (9)	0.0291 (12)	0.0213 (9)	−0.0014 (7)	0.0071 (7)	0.0018 (8)
C6	0.0277 (10)	0.0291 (11)	0.0202 (9)	0.0014 (8)	0.0117 (8)	0.0027 (8)
C13	0.0265 (9)	0.0187 (9)	0.0195 (8)	−0.0010 (8)	0.0105 (7)	0.0000 (7)
C17	0.0263 (10)	0.0163 (9)	0.0178 (8)	0.0017 (7)	0.0085 (7)	0.0028 (7)
C15	0.0234 (10)	0.0300 (12)	0.0230 (10)	0.0054 (8)	0.0082 (8)	0.0030 (8)
C2	0.0220 (9)	0.0143 (9)	0.0193 (8)	0.0005 (7)	0.0087 (7)	0.0016 (7)
C5	0.0263 (10)	0.0300 (12)	0.0252 (10)	−0.0084 (9)	0.0101 (8)	0.0025 (9)
C1	0.0200 (8)	0.0149 (9)	0.0238 (9)	0.0001 (6)	0.0069 (7)	−0.0002 (7)

O2—C3	1.238 (3)	C12—C13	1.392 (3)
O3—C2	1.405 (2)	C12—C11	1.396 (3)
O3—C17	1.461 (2)	C12—H12	0.9300
O1—C1	1.226 (3)	C10—H10A	0.9600
O4—C13	1.354 (3)	C10—H10B	0.9600
O4—H4A	0.8200	C10—H10C	0.9600
N2—C3	1.350 (3)	C16—C15	1.392 (3)
N2—C2	1.441 (2)	C16—C11	1.392 (3)
N2—C10	1.474 (2)	C16—H16	0.9300
N1—C1	1.354 (3)	C11—C17	1.492 (3)
N1—C8	1.422 (2)	C14—C15	1.380 (3)
N1—H1	0.8600	C14—C13	1.404 (3)
C8—C7	1.397 (3)	C14—H14	0.9300
C8—C9	1.402 (3)	C6—C5	1.391 (3)
C9—C4	1.403 (3)	C6—H6	0.9300
C9—C3	1.489 (3)	C17—C2	1.486 (3)
C7—C6	1.387 (3)	C17—H17	0.9800
C7—H7	0.9300	C15—H15	0.9300
C4—C5	1.373 (3)	C2—C1	1.518 (3)
C4—H4	0.9300	C5—H5	0.9300
C2—O3—C17	62.43 (12)	C11—C16—H16	120.2
C13—O4—H4A	109.5	C16—C11—C12	120.29 (19)
C3—N2—C2	121.51 (17)	C16—C11—C17	117.10 (18)
C3—N2—C10	120.16 (17)	C12—C11—C17	122.59 (17)
C2—N2—C10	118.28 (17)	C15—C14—C13	119.7 (2)
C1—N1—C8	125.99 (16)	C15—C14—H14	120.1
C1—N1—H1	117.0	C13—C14—H14	120.1
C8—N1—H1	117.0	C7—C6—C5	119.99 (19)
C7—C8—C9	119.68 (18)	C7—C6—H6	120.0
C7—C8—N1	116.53 (18)	C5—C6—H6	120.0
C9—C8—N1	123.70 (17)	O4—C13—C12	122.98 (18)
C4—C9—C8	118.62 (18)	O4—C13—C14	117.11 (18)
C4—C9—C3	116.31 (19)	C12—C13—C14	119.9 (2)
C8—C9—C3	124.83 (17)	O3—C17—C2	56.95 (11)
C6—C7—C8	120.4 (2)	O3—C17—C11	118.78 (16)
C6—C7—H7	119.8	C2—C17—C11	126.41 (18)
C8—C7—H7	119.8	O3—C17—H17	114.1
C5—C4—C9	121.4 (2)	C2—C17—H17	114.1
C5—C4—H4	119.3	C11—C17—H17	114.1
C9—C4—H4	119.3	C14—C15—C16	120.80 (18)
O2—C3—N2	121.27 (19)	C14—C15—H15	119.6
O2—C3—C9	120.14 (19)	C16—C15—H15	119.6
N2—C3—C9	118.58 (18)	O3—C2—N2	114.81 (16)
C13—C12—C11	119.76 (18)	O3—C2—C17	60.63 (12)
C13—C12—H12	120.1	N2—C2—C17	123.77 (17)
C11—C12—H12	120.1	O3—C2—C1	115.22 (16)
N2—C10—H10A	109.5	N2—C2—C1	113.46 (16)
N2—C10—H10B	109.5	C17—C2—C1	117.85 (17)
H10A—C10—H10B	109.5	C4—C5—C6	119.79 (19)
N2—C10—H10C	109.5	C4—C5—H5	120.1
H10A—C10—H10C	109.5	C6—C5—H5	120.1
H10B—C10—H10C	109.5	O1—C1—N1	122.65 (19)
C15—C16—C11	119.5 (2)	O1—C1—C2	122.34 (19)
C15—C16—H16	120.2	N1—C1—C2	114.97 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.13	2.893 (2)	148
O4—H4A···O1ii	0.82	1.95	2.7689 (17)	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.13	2.893 (2)	148
O4—H4A⋯O1ii	0.82	1.95	2.7689 (17)	173

Symmetry codes: (i) ; (ii) .