8-Hydr-oxy-8-phenyl-2,3,7,8-tetra-hydro-6H-1,4-dioxino[2,3-f]isoindol-6-one.

In the title compound, C(16)H(13)NO(4), the indole system is essentially planar, whereas the dioxane ring adopts a twist conformation. The mol-ecules are linked into chains by -O- H⋯O=C- hydrogen bonds and these chains are linked into rods by means of N-H⋯O hydrogen bonds. Exept for weak C-H⋯O inter-actions between the rods, no other inter-molecular contacts of inter-est are present.

Related literature

For details of the appropriate nitrile hydrolysis, see: Moorthy & Singhal (2005 ▶).

Experimental

Crystal data

C16H13NO4

M = 283.27

Monoclinic,

a = 8.6001 (17) Å

b = 27.005 (5) Å

c = 5.7221 (5) Å

β = 92.602 (10)°

V = 1327.6 (4) Å3

Z = 4

Cu Kα radiation

μ = 0.85 mm−1

T = 291 (2) K

0.08 × 0.06 × 0.04 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: none

2892 measured reflections

2653 independent reflections

1784 reflections with I > 2σ(I)

R int = 0.025

2 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.147

S = 1.05

2653 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2000 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003012/rk2073sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003012/rk2073Isup2.hkl

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

C16H13NO4	F000 = 592
Mr = 283.27	Dx = 1.417 Mg m−3
Monoclinic, P21/c	Melting point = 485–486 K
Hall symbol: -P 2ybc	Cu Kα radiation λ = 1.54184 Å
a = 8.6001 (17) Å	Cell parameters from 25 reflections
b = 27.005 (5) Å	θ = 26–42º
c = 5.7221 (5) Å	µ = 0.85 mm−1
β = 92.602 (10)º	T = 291 (2) K
V = 1327.6 (4) Å3	Prism, colorless
Z = 4	0.08 × 0.06 × 0.04 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.025
Radiation source: fine-focus sealed tube	θmax = 73.9º
Monochromator: graphite	θmin = 3.3º
T = 291(2) K	h = −10→10
Non–profiled ω scans	k = 0→32
Absorption correction: none	l = 0→7
2892 measured reflections	2 standard reflections
2653 independent reflections	every 120 min
1784 reflections with I > 2σ(I)	intensity decay: none

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.054	w = 1/[σ2(Fo2) + (0.061P)2 + 0.4104P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.147	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.23 e Å−3
2653 reflections	Δρmin = −0.24 e Å−3
192 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (6)
Secondary atom site location: difference Fourier map

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	0.3338 (2)	0.50617 (7)	1.1457 (3)	0.0654 (5)
O2	0.3093 (2)	0.70474 (6)	0.9980 (3)	0.0549 (5)
H2	0.2370	0.6906	1.0585	0.082*
O3	0.1250 (2)	0.65694 (7)	0.3005 (3)	0.0568 (5)
O4	0.1351 (3)	0.48070 (7)	0.7532 (4)	0.0737 (6)
N7	0.2877 (2)	0.68919 (8)	0.5922 (3)	0.0498 (5)
H7	0.2972	0.7182	0.5321	0.060*
C2	0.2445 (4)	0.46150 (12)	1.1374 (6)	0.0810 (10)
H2A	0.1463	0.4671	1.2100	0.097*
H2B	0.3003	0.4360	1.2259	0.097*
C3	0.2138 (5)	0.44427 (12)	0.8942 (7)	0.0878 (11)
H3A	0.3117	0.4361	0.8260	0.105*
H3B	0.1510	0.4144	0.8956	0.105*
C5	0.1581 (3)	0.56216 (9)	0.6119 (4)	0.0536 (6)
H5	0.0937	0.5541	0.4826	0.064*
C6	0.2011 (3)	0.65333 (9)	0.4881 (4)	0.0467 (6)
C8	0.3642 (3)	0.67510 (9)	0.8154 (4)	0.0455 (6)
C9	0.3521 (3)	0.58711 (9)	1.0021 (4)	0.0498 (6)
H9	0.4163	0.5955	1.1313	0.060*
C10	0.2183 (3)	0.60935 (9)	0.6404 (4)	0.0467 (6)
C11	0.3138 (3)	0.62151 (9)	0.8321 (4)	0.0446 (5)
C12	0.1965 (3)	0.52745 (10)	0.7811 (5)	0.0542 (6)
C13	0.2925 (3)	0.53960 (9)	0.9759 (4)	0.0510 (6)
C14	0.5399 (3)	0.68000 (9)	0.8127 (4)	0.0458 (6)
C15	0.6197 (3)	0.66247 (10)	0.6231 (4)	0.0555 (6)
H15	0.5636	0.6499	0.4937	0.067*
C16	0.7790 (3)	0.66338 (11)	0.6228 (5)	0.0645 (7)
H16	0.8301	0.6514	0.4946	0.077*
C17	0.8631 (4)	0.68214 (12)	0.8136 (5)	0.0683 (8)
H17	0.9712	0.6829	0.8143	0.082*
C18	0.7876 (3)	0.69959 (11)	1.0011 (5)	0.0678 (8)
H18	0.8449	0.7121	1.1297	0.081*
C19	0.6268 (3)	0.69889 (10)	1.0022 (4)	0.0561 (7)
H19	0.5767	0.7112	1.1307	0.067*

	U11	U22	U33	U12	U13	U23
O1	0.0765 (13)	0.0525 (11)	0.0666 (12)	−0.0020 (9)	−0.0039 (10)	0.0182 (9)
O2	0.0654 (12)	0.0516 (10)	0.0488 (10)	−0.0046 (8)	0.0138 (8)	−0.0083 (8)
O3	0.0575 (11)	0.0718 (12)	0.0406 (9)	−0.0020 (9)	−0.0038 (8)	0.0054 (8)
O4	0.0847 (15)	0.0480 (11)	0.0870 (15)	−0.0136 (10)	−0.0131 (12)	0.0040 (10)
N7	0.0603 (13)	0.0463 (11)	0.0421 (10)	−0.0032 (9)	−0.0049 (9)	0.0071 (9)
C2	0.097 (3)	0.0529 (18)	0.093 (2)	−0.0106 (16)	0.0003 (19)	0.0230 (17)
C3	0.107 (3)	0.0513 (18)	0.104 (3)	−0.0006 (18)	−0.011 (2)	0.0065 (18)
C5	0.0578 (15)	0.0547 (15)	0.0480 (13)	−0.0073 (12)	−0.0020 (11)	−0.0051 (12)
C6	0.0464 (13)	0.0567 (15)	0.0371 (11)	0.0029 (11)	0.0021 (10)	0.0008 (10)
C8	0.0575 (14)	0.0446 (13)	0.0343 (11)	−0.0017 (11)	−0.0001 (10)	−0.0005 (9)
C9	0.0564 (14)	0.0511 (14)	0.0417 (12)	−0.0030 (11)	−0.0005 (10)	0.0034 (11)
C10	0.0512 (13)	0.0500 (14)	0.0388 (11)	−0.0035 (11)	0.0017 (10)	−0.0004 (10)
C11	0.0505 (13)	0.0459 (13)	0.0373 (12)	−0.0014 (10)	0.0022 (10)	0.0010 (10)
C12	0.0608 (16)	0.0454 (14)	0.0565 (15)	−0.0078 (12)	0.0027 (12)	−0.0041 (12)
C13	0.0556 (14)	0.0469 (14)	0.0506 (13)	−0.0001 (11)	0.0042 (11)	0.0074 (11)
C14	0.0567 (14)	0.0436 (13)	0.0370 (11)	−0.0025 (11)	0.0011 (10)	0.0021 (10)
C15	0.0610 (16)	0.0649 (17)	0.0407 (12)	−0.0025 (13)	0.0027 (11)	−0.0039 (12)
C16	0.0606 (16)	0.074 (2)	0.0594 (17)	0.0007 (14)	0.0109 (13)	−0.0030 (15)
C17	0.0570 (16)	0.076 (2)	0.0716 (19)	−0.0002 (14)	0.0011 (14)	0.0022 (16)
C18	0.0635 (18)	0.076 (2)	0.0624 (17)	−0.0039 (15)	−0.0152 (14)	−0.0050 (15)
C19	0.0672 (17)	0.0599 (16)	0.0404 (12)	0.0001 (13)	−0.0040 (11)	−0.0032 (11)

O1—C13	1.362 (3)	C8—C11	1.515 (3)
O1—C2	1.430 (4)	C8—C14	1.518 (3)
O2—C8	1.415 (3)	C9—C11	1.374 (3)
O2—H2	0.8200	C9—C13	1.387 (3)
O3—C6	1.236 (3)	C9—H9	0.9300
O4—C12	1.375 (3)	C10—C11	1.380 (3)
O4—C3	1.424 (4)	C12—C13	1.396 (3)
N7—C6	1.344 (3)	C14—C19	1.386 (3)
N7—C8	1.460 (3)	C14—C15	1.393 (3)
N7—H7	0.8600	C15—C16	1.370 (4)
C2—C3	1.480 (5)	C15—H15	0.9300
C2—H2A	0.9700	C16—C17	1.378 (4)
C2—H2B	0.9700	C16—H16	0.9300
C3—H3A	0.9700	C17—C18	1.363 (4)
C3—H3B	0.9700	C17—H17	0.9300
C5—C12	1.376 (4)	C18—C19	1.384 (4)
C5—C10	1.382 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—H19	0.9300
C6—C10	1.477 (3)
C13—O1—C2	114.4 (2)	C13—C9—H9	120.9
C8—O2—H2	109.5	C11—C10—C5	121.3 (2)
C12—O4—C3	113.5 (2)	C11—C10—C6	108.5 (2)
C6—N7—C8	114.7 (2)	C5—C10—C6	130.2 (2)
C6—N7—H7	122.6	C9—C11—C10	121.1 (2)
C8—N7—H7	122.6	C9—C11—C8	129.1 (2)
O1—C2—C3	111.7 (3)	C10—C11—C8	109.8 (2)
O1—C2—H2A	109.3	O4—C12—C5	117.7 (2)
C3—C2—H2A	109.3	O4—C12—C13	121.2 (2)
O1—C2—H2B	109.3	C5—C12—C13	121.0 (2)
C3—C2—H2B	109.3	O1—C13—C9	116.9 (2)
H2A—C2—H2B	107.9	O1—C13—C12	122.7 (2)
O4—C3—C2	112.1 (3)	C9—C13—C12	120.4 (2)
O4—C3—H3A	109.2	C19—C14—C15	117.8 (2)
C2—C3—H3A	109.2	C19—C14—C8	121.7 (2)
O4—C3—H3B	109.2	C15—C14—C8	120.3 (2)
C2—C3—H3B	109.2	C16—C15—C14	121.5 (3)
H3A—C3—H3B	107.9	C16—C15—H15	119.2
C12—C5—C10	117.9 (2)	C14—C15—H15	119.2
C12—C5—H5	121.0	C15—C16—C17	119.6 (3)
C10—C5—H5	121.0	C15—C16—H16	120.2
O3—C6—N7	126.1 (2)	C17—C16—H16	120.2
O3—C6—C10	127.7 (2)	C18—C17—C16	119.9 (3)
N7—C6—C10	106.23 (19)	C18—C17—H17	120.0
O2—C8—N7	110.3 (2)	C16—C17—H17	120.0
O2—C8—C11	112.82 (19)	C17—C18—C19	120.7 (3)
N7—C8—C11	100.69 (18)	C17—C18—H18	119.7
O2—C8—C14	108.89 (19)	C19—C18—H18	119.7
N7—C8—C14	112.20 (19)	C18—C19—C14	120.4 (3)
C11—C8—C14	111.8 (2)	C18—C19—H19	119.8
C11—C9—C13	118.2 (2)	C14—C19—H19	119.8
C11—C9—H9	120.9
C13—O1—C2—C3	40.4 (4)	C3—O4—C12—C5	162.9 (3)
C12—O4—C3—C2	45.2 (4)	C3—O4—C12—C13	−18.1 (4)
O1—C2—C3—O4	−57.6 (4)	C10—C5—C12—O4	179.4 (2)
C8—N7—C6—O3	179.2 (2)	C10—C5—C12—C13	0.3 (4)
C8—N7—C6—C10	−1.7 (3)	C2—O1—C13—C9	167.3 (3)
C6—N7—C8—O2	−117.5 (2)	C2—O1—C13—C12	−13.5 (4)
C6—N7—C8—C11	1.8 (3)	C11—C9—C13—O1	179.3 (2)
C6—N7—C8—C14	120.9 (2)	C11—C9—C13—C12	0.1 (4)
C12—C5—C10—C11	−0.1 (4)	O4—C12—C13—O1	1.5 (4)
C12—C5—C10—C6	178.4 (3)	C5—C12—C13—O1	−179.5 (2)
O3—C6—C10—C11	179.9 (2)	O4—C12—C13—C9	−179.3 (2)
N7—C6—C10—C11	0.8 (3)	C5—C12—C13—C9	−0.4 (4)
O3—C6—C10—C5	1.3 (4)	O2—C8—C14—C19	16.7 (3)
N7—C6—C10—C5	−177.8 (3)	N7—C8—C14—C19	139.1 (2)
C13—C9—C11—C10	0.2 (4)	C11—C8—C14—C19	−108.6 (3)
C13—C9—C11—C8	−178.9 (2)	O2—C8—C14—C15	−167.4 (2)
C5—C10—C11—C9	−0.2 (4)	N7—C8—C14—C15	−45.1 (3)
C6—C10—C11—C9	−178.9 (2)	C11—C8—C14—C15	67.2 (3)
C5—C10—C11—C8	179.0 (2)	C19—C14—C15—C16	0.5 (4)
C6—C10—C11—C8	0.3 (3)	C8—C14—C15—C16	−175.6 (2)
O2—C8—C11—C9	−64.5 (3)	C14—C15—C16—C17	−0.2 (4)
N7—C8—C11—C9	178.0 (2)	C15—C16—C17—C18	0.1 (5)
C14—C8—C11—C9	58.6 (3)	C16—C17—C18—C19	−0.3 (5)
O2—C8—C11—C10	116.3 (2)	C17—C18—C19—C14	0.5 (5)
N7—C8—C11—C10	−1.2 (3)	C15—C14—C19—C18	−0.6 (4)
C14—C8—C11—C10	−120.5 (2)	C8—C14—C19—C18	175.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.82	1.95	2.725 (3)	158
N7—H7···O2ii	0.86	2.09	2.922 (3)	161
C5—H5···O4iii	0.93	2.52	3.404 (3)	160
C19—H19···O2	0.93	2.40	2.734 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.82	1.95	2.725 (3)	158
N7—H7⋯O2ii	0.86	2.09	2.922 (3)	161
C5—H5⋯O4iii	0.93	2.52	3.404 (3)	160
C19—H19⋯O2	0.93	2.40	2.734 (4)	101

Symmetry codes: (i) ; (ii) ; (iii) .