Crystal structure of 1-ethyl-spiro-[imid-az-olidine-4,1'-indane]-2,5-dione.

In the title compound, C13H14N2O2, the C5 ring has an envelope conformation with the C atom adjacent to the quaternary C being the flap. The five atoms comprising the imidazolidine-2,4-dione ring are almost planar (r.m.s. deviation = 0.004 Å). The dihedral angle between the five-membered rings is 89.66 (10)°. In the crystal, inversion-related mol-ecules are connected via {⋯HNCO}2 synthons. These are linked into a helical supra-molecular chain along [010] by C-H⋯O inter-actions.

Related literature

For background to the synthesis and biological activity of hydantoin derivatives, see: Manjunath et al. (2011 ▶, 2012 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H14N2O2

M = 230.26

Monoclinic,

a = 13.7183 (10) Å

b = 6.2040 (5) Å

c = 15.1944 (11) Å

β = 112.865 (3)°

V = 1191.56 (16) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.867, T max = 0.867

6730 measured reflections

1953 independent reflections

1742 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.07

1953 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814017097/tk5331sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017097/tk5331Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814017097/tk5331Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814017097/tk5331fig1.tif

A view of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S1600536814017097/tk5331fig2.tif

A view along the b axis of the crystal packing of the title compound.

CCDC reference: 1015714

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H14N2O2	Z = 4
Mr = 230.26	F(000) = 488
Monoclinic, P21/n	Dx = 1.284 Mg m−3
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 13.7183 (10) Å	µ = 0.72 mm−1
b = 6.2040 (5) Å	T = 296 K
c = 15.1944 (11) Å	Block, colourless
β = 112.865 (3)°	0.23 × 0.22 × 0.21 mm
V = 1191.56 (16) Å3

Bruker X8 Proteum diffractometer	1742 reflections with I > 2σ(I)
Detector resolution: 10.7 pixels mm-1	Rint = 0.027
φ and ω scans	θmax = 64.5°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −15→15
Tmin = 0.867, Tmax = 0.867	k = −3→7
6730 measured reflections	l = −16→17
1953 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.120	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.277P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
1953 reflections	Δρmax = 0.23 e Å−3
156 parameters	Δρmin = −0.21 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0109 (13)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O6	0.76182 (10)	−0.0363 (2)	0.94368 (9)	0.0601 (5)
O7	0.55113 (10)	0.2685 (2)	1.07873 (8)	0.0578 (4)
N1	0.66453 (10)	0.0760 (2)	1.02847 (9)	0.0424 (4)
N3	0.57906 (12)	0.3540 (2)	0.94258 (10)	0.0519 (5)
C2	0.59249 (12)	0.2404 (3)	1.02119 (11)	0.0434 (5)
C4	0.64286 (12)	0.2741 (2)	0.89160 (11)	0.0409 (5)
C5	0.69854 (12)	0.0850 (2)	0.95511 (11)	0.0414 (5)
C8	0.70154 (13)	−0.0797 (3)	1.10674 (12)	0.0510 (5)
C9	0.79910 (18)	−0.0056 (4)	1.18691 (15)	0.0760 (8)
C10	0.57793 (11)	0.2115 (2)	0.78900 (10)	0.0383 (4)
C11	0.50778 (13)	0.0411 (3)	0.75563 (14)	0.0545 (6)
C12	0.45848 (16)	0.0121 (4)	0.65796 (16)	0.0713 (7)
C13	0.47830 (15)	0.1510 (4)	0.59623 (14)	0.0741 (8)
C14	0.54676 (14)	0.3205 (4)	0.62923 (13)	0.0649 (7)
C15	0.59759 (11)	0.3507 (3)	0.72680 (11)	0.0447 (5)
C16	0.67693 (15)	0.5191 (3)	0.77928 (14)	0.0586 (6)
C17	0.72378 (15)	0.4361 (3)	0.88099 (13)	0.0569 (6)
H1	0.85420	0.01810	1.16380	0.1140*
H2	0.44450	0.12930	0.53070	0.0890*
H3	0.78460	0.12630	1.21260	0.1140*
H4	0.53720	0.46290	0.92390	0.0620*
H5	0.55900	0.41400	0.58670	0.0780*
H6	0.41160	−0.10190	0.63380	0.0860*
H7	0.49420	−0.05110	0.79780	0.0650*
H8	0.73090	0.53320	0.75320	0.0700*
H9	0.64310	0.65790	0.77600	0.0700*
H10	0.73560	0.55430	0.92580	0.0680*
H11	0.79080	0.36510	0.89350	0.0680*
H12	0.64620	−0.10350	1.13040	0.0610*
H13	0.71580	−0.21600	1.08280	0.0610*
H14	0.82130	−0.11370	1.23600	0.1140*

	U11	U22	U33	U12	U13	U23
O6	0.0622 (8)	0.0624 (8)	0.0613 (8)	0.0248 (6)	0.0301 (6)	0.0006 (6)
O7	0.0702 (8)	0.0651 (8)	0.0502 (7)	0.0260 (6)	0.0366 (6)	0.0125 (6)
N1	0.0483 (7)	0.0410 (7)	0.0397 (7)	0.0137 (5)	0.0190 (6)	0.0071 (5)
N3	0.0724 (9)	0.0482 (8)	0.0425 (8)	0.0301 (7)	0.0305 (7)	0.0115 (6)
C2	0.0505 (9)	0.0436 (8)	0.0382 (8)	0.0131 (7)	0.0195 (7)	0.0021 (7)
C4	0.0489 (8)	0.0398 (8)	0.0373 (8)	0.0060 (6)	0.0205 (7)	−0.0005 (6)
C5	0.0428 (8)	0.0411 (8)	0.0400 (8)	0.0059 (7)	0.0159 (6)	−0.0035 (6)
C8	0.0549 (9)	0.0473 (9)	0.0523 (10)	0.0120 (7)	0.0225 (8)	0.0144 (8)
C9	0.0771 (13)	0.0799 (15)	0.0547 (12)	0.0073 (11)	0.0079 (10)	0.0142 (10)
C10	0.0360 (7)	0.0432 (8)	0.0382 (8)	0.0043 (6)	0.0171 (6)	0.0003 (6)
C11	0.0482 (9)	0.0568 (10)	0.0589 (11)	−0.0082 (8)	0.0211 (8)	−0.0026 (8)
C12	0.0516 (10)	0.0831 (14)	0.0681 (14)	−0.0145 (10)	0.0112 (10)	−0.0207 (11)
C13	0.0497 (10)	0.1212 (19)	0.0424 (10)	−0.0016 (12)	0.0080 (8)	−0.0116 (11)
C14	0.0503 (10)	0.1028 (16)	0.0408 (10)	0.0043 (10)	0.0167 (8)	0.0148 (10)
C15	0.0367 (8)	0.0571 (10)	0.0420 (9)	0.0049 (7)	0.0171 (7)	0.0084 (7)
C16	0.0587 (10)	0.0530 (10)	0.0633 (12)	−0.0060 (8)	0.0230 (9)	0.0116 (9)
C17	0.0621 (10)	0.0521 (10)	0.0516 (10)	−0.0131 (8)	0.0167 (8)	−0.0065 (8)

O6—C5	1.211 (2)	C14—C15	1.384 (2)
O7—C2	1.226 (2)	C15—C16	1.496 (3)
N1—C2	1.394 (2)	C16—C17	1.515 (3)
N1—C5	1.367 (2)	C8—H12	0.9700
N1—C8	1.462 (2)	C8—H13	0.9700
N3—C2	1.337 (2)	C9—H1	0.9600
N3—C4	1.462 (2)	C9—H3	0.9600
N3—H4	0.8600	C9—H14	0.9600
C4—C5	1.523 (2)	C11—H7	0.9300
C4—C10	1.515 (2)	C12—H6	0.9300
C4—C17	1.552 (3)	C13—H2	0.9300
C8—C9	1.490 (3)	C14—H5	0.9300
C10—C11	1.386 (2)	C16—H8	0.9700
C10—C15	1.382 (2)	C16—H9	0.9700
C11—C12	1.383 (3)	C17—H10	0.9700
C12—C13	1.376 (3)	C17—H11	0.9700
C13—C14	1.369 (3)
O6···C17i	3.392 (2)	C17···H2x	3.0300
O6···C14ii	3.343 (3)	H1···C5	3.0900
O7···N3iii	2.886 (2)	H1···C13x	3.0900
O6···H11	2.6800	H1···C14x	3.0600
O6···H13	2.6700	H2···C13viii	3.0700
O6···H5ii	2.6900	H2···C17ix	3.0300
O6···H10i	2.5600	H2···H11ix	2.3200
O7···H12	2.6200	H3···H14iv	2.4900
O7···H14iv	2.7700	H4···O7iii	2.0500
O7···H4iii	2.0500	H4···C2iii	2.9000
O7···H7v	2.5800	H5···O6vi	2.6900
N3···O7iii	2.886 (2)	H7···C5	3.0100
C14···O6vi	3.343 (3)	H7···O7v	2.5800
C17···O6vii	3.392 (2)	H8···C15vi	2.9900
C2···H4iii	2.9000	H9···C11vii	2.9600
C5···H1	3.0900	H10···O6vii	2.5600
C5···H7	3.0100	H11···O6	2.6800
C11···H9i	2.9600	H11···H2x	2.3200
C13···H2viii	3.0700	H12···O7	2.6200
C13···H1ix	3.0900	H13···O6	2.6700
C14···H1ix	3.0600	H14···O7xi	2.7700
C15···H8ii	2.9900	H14···H3xi	2.4900
C2—N1—C5	111.19 (12)	C4—C17—C16	106.81 (15)
C2—N1—C8	124.02 (14)	N1—C8—H12	109.00
C5—N1—C8	124.75 (14)	N1—C8—H13	109.00
C2—N3—C4	113.05 (14)	C9—C8—H12	109.00
C2—N3—H4	123.00	C9—C8—H13	109.00
C4—N3—H4	123.00	H12—C8—H13	108.00
N1—C2—N3	107.70 (14)	C8—C9—H1	109.00
O7—C2—N1	123.90 (15)	C8—C9—H3	109.00
O7—C2—N3	128.41 (17)	C8—C9—H14	109.00
N3—C4—C17	115.79 (12)	H1—C9—H3	110.00
C5—C4—C10	113.84 (11)	H1—C9—H14	109.00
C5—C4—C17	111.22 (14)	H3—C9—H14	109.00
C10—C4—C17	102.56 (13)	C10—C11—H7	121.00
N3—C4—C5	100.46 (12)	C12—C11—H7	121.00
N3—C4—C10	113.47 (14)	C11—C12—H6	120.00
O6—C5—N1	125.62 (14)	C13—C12—H6	120.00
N1—C5—C4	107.59 (13)	C12—C13—H2	119.00
O6—C5—C4	126.79 (15)	C14—C13—H2	119.00
N1—C8—C9	112.28 (16)	C13—C14—H5	121.00
C4—C10—C15	110.52 (13)	C15—C14—H5	120.00
C4—C10—C11	128.23 (14)	C15—C16—H8	111.00
C11—C10—C15	121.24 (15)	C15—C16—H9	111.00
C10—C11—C12	118.18 (18)	C17—C16—H8	111.00
C11—C12—C13	120.4 (2)	C17—C16—H9	111.00
C12—C13—C14	121.37 (19)	H8—C16—H9	109.00
C13—C14—C15	119.00 (19)	C4—C17—H10	110.00
C10—C15—C16	111.52 (14)	C4—C17—H11	110.00
C10—C15—C14	119.80 (17)	C16—C17—H10	110.00
C14—C15—C16	128.68 (17)	C16—C17—H11	110.00
C15—C16—C17	103.82 (15)	H10—C17—H11	109.00
C5—N1—C2—O7	−179.31 (16)	N3—C4—C10—C15	112.36 (15)
C5—N1—C2—N3	0.70 (19)	C5—C4—C10—C11	45.9 (2)
C8—N1—C2—O7	−1.6 (3)	C5—C4—C10—C15	−133.54 (15)
C8—N1—C2—N3	178.45 (15)	C17—C4—C10—C11	166.16 (17)
C2—N1—C5—O6	179.35 (16)	C17—C4—C10—C15	−13.28 (17)
C2—N1—C5—C4	−0.48 (17)	N3—C4—C17—C16	−103.10 (17)
C8—N1—C5—O6	1.6 (3)	C5—C4—C17—C16	143.07 (15)
C8—N1—C5—C4	−178.21 (14)	C10—C4—C17—C16	21.02 (17)
C2—N1—C8—C9	−90.8 (2)	C4—C10—C11—C12	−178.69 (18)
C5—N1—C8—C9	86.6 (2)	C15—C10—C11—C12	0.7 (3)
C4—N3—C2—O7	179.36 (17)	C4—C10—C15—C14	179.40 (16)
C4—N3—C2—N1	−0.64 (19)	C4—C10—C15—C16	0.3 (2)
C2—N3—C4—C5	0.34 (17)	C11—C10—C15—C14	−0.1 (3)
C2—N3—C4—C10	122.24 (15)	C11—C10—C15—C16	−179.18 (16)
C2—N3—C4—C17	−119.53 (16)	C10—C11—C12—C13	−0.7 (3)
N3—C4—C5—O6	−179.74 (16)	C11—C12—C13—C14	0.0 (4)
N3—C4—C5—N1	0.09 (16)	C12—C13—C14—C15	0.6 (3)
C10—C4—C5—O6	58.6 (2)	C13—C14—C15—C10	−0.6 (3)
C10—C4—C5—N1	−121.54 (15)	C13—C14—C15—C16	178.3 (2)
C17—C4—C5—O6	−56.6 (2)	C10—C15—C16—C17	13.2 (2)
C17—C4—C5—N1	123.20 (14)	C14—C15—C16—C17	−165.8 (2)
N3—C4—C10—C11	−68.2 (2)	C15—C16—C17—C4	−21.00 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H4···O7iii	0.86	2.05	2.886 (2)	163
C11—H7···O7v	0.93	2.58	3.501 (2)	173
C17—H10···O6vii	0.97	2.56	3.392 (2)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H4⋯O7i	0.86	2.05	2.886 (2)	163
C11—H7⋯O7ii	0.93	2.58	3.501 (2)	173
C17—H10⋯O6iii	0.97	2.56	3.392 (2)	143

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