3-Ethyl-5-(4-oxochroman-3-ylmethyl­ene)-1,3-imidazolidine-2,4-dione

The mol­ecule of the title compound, C₁₅H₁₂N₂O₄, is planar, with a dihedral angle of 0.97 (4)° between the planes of the five-membered imidazolidine and benzopyran ring systems. The crystal structure is stabilized by C—H...O and N—H...O hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.114
• Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)         600 Deg.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  O4      ..       2.67 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Ethyl-5-(4-oxochroman-3-ylmethylene)-1,3-imidazolidine-2,4-dione

Crystal data

C15H12N2O4	Z = 2
Mr = 284.27	F(000) = 296
Triclinic, P1	Dx = 1.513 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3407 (4) Å	Cell parameters from 9747 reflections
b = 10.4070 (8) Å	θ = 3.1–28.5°
c = 12.0223 (9) Å	µ = 0.11 mm^−1
α = 106.953 (6)°	T = 295 K
β = 101.066 (6)°	Prism, colourless
γ = 92.143 (6)°	0.26 × 0.2 × 0.1 mm
V = 624.18 (9) Å^3

Data collection

Stoe IPDS-II diffractometer	2373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω scans	θmax = 28.5°, θmin = 3.1°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −6→7
Tmin = 0.972, Tmax = 0.989	k = −13→13
9747 measured reflections	l = −16→16
3131 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.095P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.114	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.34 e Å^−3
3131 reflections	Δρmin = −0.19 e Å^−3
203 parameters

Special details

Experimental. IR (cm-1) (γ pyrone CO): 1671; 1H NMR (DMSO-d6, 400?MHz, γ, p.p.m.): 1.11 (t, 3H, –CH3), 3.48 (q, 2H, –CH2–), 6.42 (s, 1H, =CH), 7.52 (ddd, 1H, 6-H), 7.70 (d, 1H, j8,7 = 8.80 Hz, 8-H), 7.84 (ddd, 1H, 7-H), 8.11 (dd, 1H, j5,6= 8.40 Hz, j5,7= 1.60 Hz, 5-H), 8.74 (s, 1H, 2-H), 10.53 (s, 1H, NH), ESMS[ES (+), m/z]: 285 (M+1)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O4	0.0983 (2)	0.49490 (11)	−0.16132 (9)	0.0264 (2)
H1	0.497 (4)	0.1214 (18)	0.4248 (17)	0.027 (5)*
H10	0.179 (4)	0.3843 (18)	0.0156 (16)	0.025 (4)*
H11	0.668 (4)	0.2149 (19)	−0.1303 (17)	0.032 (5)*
O1	0.3566 (2)	0.23695 (10)	0.27032 (9)	0.0236 (2)
O2	0.7307 (2)	0.14083 (11)	−0.00515 (9)	0.0259 (2)
O3	0.6898 (2)	0.25287 (11)	−0.33877 (9)	0.0274 (2)
C5	0.6738 (3)	0.11573 (13)	0.17631 (12)	0.0204 (3)
N2	0.3813 (2)	0.39021 (12)	−0.27353 (11)	0.0224 (3)
N1	0.5705 (2)	0.27450 (12)	−0.15918 (11)	0.0223 (3)
C13	0.5651 (3)	0.29902 (14)	−0.26467 (13)	0.0221 (3)
C7	0.6140 (3)	0.17199 (13)	0.07652 (12)	0.0199 (3)
C12	0.2636 (3)	0.41865 (14)	−0.17818 (12)	0.0210 (3)
C8	0.4109 (3)	0.26248 (13)	0.08340 (12)	0.0198 (3)
C9	0.2985 (3)	0.28713 (14)	0.17874 (12)	0.0216 (3)
H9	0.1686	0.3443	0.1807	0.026*
C14	0.3221 (3)	0.44218 (15)	−0.37468 (13)	0.0246 (3)
H14A	0.4775	0.4531	−0.4029	0.03*
H14B	0.2606	0.5303	−0.3492	0.03*
C15	0.1211 (3)	0.34943 (15)	−0.47615 (13)	0.0272 (3)
H15A	0.178	0.261	−0.4996	0.041*
H15B	0.0955	0.3846	−0.5425	0.041*
H15C	−0.0375	0.3441	−0.4505	0.041*
C1	0.5904 (3)	0.09625 (15)	0.36340 (13)	0.0253 (3)
C11	0.3856 (3)	0.33805 (13)	−0.10197 (12)	0.0203 (3)
C10	0.3145 (3)	0.33350 (14)	−0.00244 (12)	0.0206 (3)
C6	0.5421 (3)	0.14943 (14)	0.26884 (13)	0.0213 (3)
C2	0.7731 (3)	0.00679 (15)	0.36424 (13)	0.0263 (3)
H2	0.8067	−0.0305	0.4264	0.032*
C4	0.8606 (3)	0.02510 (14)	0.18031 (13)	0.0236 (3)
H4	0.9519	0.0014	0.12	0.028*
C3	0.9093 (3)	−0.02900 (15)	0.27333 (14)	0.0264 (3)
H3	1.0329	−0.0893	0.2755	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0252 (5)	0.0283 (5)	0.0287 (5)	0.0126 (4)	0.0074 (4)	0.0109 (4)
O1	0.0237 (5)	0.0279 (5)	0.0244 (5)	0.0100 (4)	0.0089 (4)	0.0124 (4)
O2	0.0266 (5)	0.0316 (5)	0.0255 (5)	0.0141 (4)	0.0116 (4)	0.0127 (4)
O3	0.0295 (6)	0.0327 (5)	0.0263 (5)	0.0120 (4)	0.0130 (4)	0.0130 (4)
C5	0.0189 (6)	0.0185 (6)	0.0235 (6)	0.0042 (5)	0.0028 (5)	0.0067 (5)
N2	0.0249 (6)	0.0230 (6)	0.0222 (6)	0.0084 (5)	0.0057 (5)	0.0103 (5)
N1	0.0223 (6)	0.0261 (6)	0.0231 (6)	0.0108 (5)	0.0085 (5)	0.0111 (5)
C13	0.0214 (7)	0.0233 (6)	0.0231 (6)	0.0053 (5)	0.0053 (5)	0.0089 (5)
C7	0.0183 (6)	0.0190 (6)	0.0217 (6)	0.0040 (5)	0.0031 (5)	0.0058 (5)
C12	0.0213 (7)	0.0203 (6)	0.0219 (6)	0.0051 (5)	0.0047 (5)	0.0070 (5)
C8	0.0197 (7)	0.0196 (6)	0.0207 (6)	0.0041 (5)	0.0043 (5)	0.0065 (5)
C9	0.0205 (7)	0.0219 (6)	0.0247 (7)	0.0072 (5)	0.0066 (5)	0.0090 (5)
C14	0.0256 (7)	0.0280 (7)	0.0255 (7)	0.0075 (6)	0.0065 (6)	0.0148 (6)
C15	0.0290 (8)	0.0298 (7)	0.0242 (7)	0.0087 (6)	0.0062 (6)	0.0092 (6)
C1	0.0253 (7)	0.0288 (7)	0.0243 (7)	0.0039 (6)	0.0068 (6)	0.0108 (6)
C11	0.0190 (6)	0.0193 (6)	0.0226 (6)	0.0057 (5)	0.0047 (5)	0.0058 (5)
C10	0.0194 (6)	0.0198 (6)	0.0230 (6)	0.0061 (5)	0.0054 (5)	0.0059 (5)
C6	0.0194 (6)	0.0200 (6)	0.0243 (7)	0.0046 (5)	0.0037 (5)	0.0067 (5)
C2	0.0262 (7)	0.0267 (7)	0.0271 (7)	0.0016 (6)	−0.0001 (6)	0.0137 (6)
C4	0.0224 (7)	0.0220 (6)	0.0263 (7)	0.0055 (5)	0.0041 (5)	0.0075 (5)
C3	0.0240 (7)	0.0229 (7)	0.0318 (7)	0.0070 (5)	0.0013 (6)	0.0100 (6)

Geometric parameters (Å, º)

O4—C12	1.2151 (17)	C9—H9	0.93
O1—C9	1.3407 (17)	C14—C15	1.518 (2)
O1—C6	1.3698 (16)	C14—H14A	0.97
O2—C7	1.2336 (17)	C14—H14B	0.97
O3—C13	1.2121 (18)	C15—H15A	0.96
C5—C6	1.395 (2)	C15—H15B	0.96
C5—C4	1.4018 (19)	C15—H15C	0.96
C5—C7	1.4699 (19)	C1—C2	1.374 (2)
N2—C12	1.3747 (18)	C1—C6	1.389 (2)
N2—C13	1.4016 (18)	C1—H1	0.949 (19)
N2—C14	1.4560 (17)	C11—C10	1.336 (2)
N1—C13	1.3600 (19)	C10—H10	0.936 (19)
N1—C11	1.3896 (18)	C2—C3	1.397 (2)
N1—H11	0.92 (2)	C2—H2	0.93
C7—C8	1.4614 (19)	C4—C3	1.379 (2)
C12—C11	1.4925 (19)	C4—H4	0.93
C8—C9	1.358 (2)	C3—H3	0.93
C8—C10	1.4647 (18)
C9—O1—C6	118.46 (11)	C15—C14—H14B	109.2
C6—C5—C4	118.13 (13)	H14A—C14—H14B	107.9
C6—C5—C7	120.66 (12)	C14—C15—H15A	109.5
C4—C5—C7	121.19 (13)	C14—C15—H15B	109.5
C12—N2—C13	111.45 (11)	H15A—C15—H15B	109.5
C12—N2—C14	125.83 (12)	C14—C15—H15C	109.5
C13—N2—C14	122.69 (12)	H15A—C15—H15C	109.5
C13—N1—C11	112.00 (12)	H15B—C15—H15C	109.5
C13—N1—H11	126.4 (12)	C2—C1—C6	118.26 (14)
C11—N1—H11	121.1 (12)	C2—C1—H1	121.9 (11)
O3—C13—N1	128.53 (13)	C6—C1—H1	119.9 (11)
O3—C13—N2	125.16 (13)	C10—C11—N1	131.50 (13)
N1—C13—N2	106.31 (12)	C10—C11—C12	123.50 (13)
O2—C7—C8	125.01 (13)	N1—C11—C12	104.99 (12)
O2—C7—C5	120.08 (12)	C11—C10—C8	131.40 (13)
C8—C7—C5	114.90 (12)	C11—C10—H10	114.4 (11)
O4—C12—N2	126.19 (13)	C8—C10—H10	114.2 (11)
O4—C12—C11	128.72 (13)	O1—C6—C1	116.61 (13)
N2—C12—C11	105.08 (11)	O1—C6—C5	121.19 (12)
C9—C8—C7	118.48 (12)	C1—C6—C5	122.20 (13)
C9—C8—C10	114.92 (12)	C1—C2—C3	121.13 (14)
C7—C8—C10	126.59 (12)	C1—C2—H2	119.4
O1—C9—C8	126.29 (13)	C3—C2—H2	119.4
O1—C9—H9	116.9	C3—C4—C5	120.24 (14)
C8—C9—H9	116.9	C3—C4—H4	119.9
N2—C14—C15	112.24 (12)	C5—C4—H4	119.9
N2—C14—H14A	109.2	C4—C3—C2	120.02 (14)
C15—C14—H14A	109.2	C4—C3—H3	120
N2—C14—H14B	109.2	C2—C3—H3	120
C11—N1—C13—O3	−175.36 (15)	C13—N1—C11—C10	174.91 (15)
C11—N1—C13—N2	4.25 (16)	C13—N1—C11—C12	−4.09 (16)
C12—N2—C13—O3	176.97 (14)	O4—C12—C11—C10	4.0 (2)
C14—N2—C13—O3	−1.0 (2)	N2—C12—C11—C10	−176.84 (13)
C12—N2—C13—N1	−2.66 (16)	O4—C12—C11—N1	−176.87 (14)
C14—N2—C13—N1	179.33 (13)	N2—C12—C11—N1	2.26 (14)
C6—C5—C7—O2	−179.56 (13)	N1—C11—C10—C8	1.8 (3)
C4—C5—C7—O2	−0.8 (2)	C12—C11—C10—C8	−179.37 (14)
C6—C5—C7—C8	−0.20 (19)	C9—C8—C10—C11	176.85 (15)
C4—C5—C7—C8	178.60 (12)	C7—C8—C10—C11	−2.1 (2)
C13—N2—C12—O4	179.37 (14)	C9—O1—C6—C1	−177.89 (13)
C14—N2—C12—O4	−2.7 (2)	C9—O1—C6—C5	1.85 (19)
C13—N2—C12—C11	0.20 (15)	C2—C1—C6—O1	179.24 (12)
C14—N2—C12—C11	178.14 (13)	C2—C1—C6—C5	−0.5 (2)
O2—C7—C8—C9	179.70 (14)	C4—C5—C6—O1	−179.76 (12)
C5—C7—C8—C9	0.38 (18)	C7—C5—C6—O1	−0.9 (2)
O2—C7—C8—C10	−1.4 (2)	C4—C5—C6—C1	0.0 (2)
C5—C7—C8—C10	179.30 (13)	C7—C5—C6—C1	178.80 (13)
C6—O1—C9—C8	−1.7 (2)	C6—C1—C2—C3	0.7 (2)
C7—C8—C9—O1	0.6 (2)	C6—C5—C4—C3	0.4 (2)
C10—C8—C9—O1	−178.44 (13)	C7—C5—C4—C3	−178.43 (13)
C12—N2—C14—C15	−91.48 (17)	C5—C4—C3—C2	−0.2 (2)
C13—N2—C14—C15	86.24 (17)	C1—C2—C3—C4	−0.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O2	0.93 (2)	1.86 (2)	2.6607 (17)	142.9 (18)
C10—H10···O4	0.93 (2)	2.674 (19)	2.995 (2)	101.0 (13)