Phenyl 2-oxoimidazolidine-1-carboxyl­ate

In the title compound, C₁₀H₁₀N₂O₃, the five-membered imidazolidine ring is planar, with an r.m.s. derivation of 0.0243 (1)Å. The dihedral angle between the imidazolidine ring and the phenyl ring is 78.83 (2)°. A centrosymmetric ring is formed by a pair of N—H...O hydrogen bonds, creating a dimer; C—H...O hydrogen bonds connect these dimers into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.064
• wR factor = 0.131
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C1     -C6            1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  O3      ..       2.62 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10B   ..  O2      ..       2.83 Ang.

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

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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Bruker, 2002); software used to prepare material for publication: SHELXL97.

Phenyl 2-oxoimidazolidine-1-carboxylate

Crystal data

C10H10N2O3	F(000) = 432
Mr = 206.20	Dx = 1.418 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1260 reflections
a = 6.3535 (8) Å	θ = 2.3–24.3°
b = 14.0240 (18) Å	µ = 0.11 mm^−1
c = 10.8840 (13) Å	T = 298 K
β = 95.207 (3)°	Block, colourless
V = 965.8 (2) Å^3	0.15 × 0.12 × 0.07 mm
Z = 4

Data collection

Bruker APEX area-detector diffractometer	1704 independent reflections
Radiation source: fine-focus sealed tube	1156 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→7
Tmin = 0.984, Tmax = 0.993	k = −16→16
4994 measured reflections	l = −9→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0452P)^2 + 0.232P] where P = (Fo^2 + 2Fc^2)/3
1704 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
O1	0.2082 (3)	0.47526 (13)	0.33051 (19)	0.0536 (6)
O2	0.0051 (3)	0.35450 (15)	0.25090 (19)	0.0601 (7)
O3	−0.3326 (3)	0.42602 (14)	0.09373 (19)	0.0597 (7)
N1	−0.0379 (4)	0.50807 (15)	0.1801 (2)	0.0431 (6)
N2	−0.2653 (4)	0.58139 (16)	0.0497 (2)	0.0558 (7)
H2	−0.3772	0.5918	0.0010	0.067*
C1	0.3251 (4)	0.41197 (19)	0.4110 (3)	0.0417 (7)
C2	0.5033 (5)	0.3720 (2)	0.3745 (3)	0.0560 (9)
H2A	0.5436	0.3830	0.2957	0.067*
C3	0.6242 (5)	0.3145 (2)	0.4567 (4)	0.0655 (10)
H3	0.7473	0.2868	0.4331	0.079*
C4	0.5645 (6)	0.2983 (2)	0.5711 (4)	0.0627 (10)
H4	0.6455	0.2589	0.6255	0.075*
C5	0.3858 (6)	0.3397 (2)	0.6067 (3)	0.0665 (10)
H5	0.3461	0.3291	0.6857	0.080*
C6	0.2637 (5)	0.3972 (2)	0.5261 (3)	0.0598 (9)
H6	0.1414	0.4255	0.5499	0.072*
C7	0.0525 (4)	0.4363 (2)	0.2535 (3)	0.0420 (7)
C8	−0.2270 (5)	0.4984 (2)	0.1047 (3)	0.0416 (7)
C9	0.0451 (5)	0.60541 (19)	0.1756 (3)	0.0481 (8)
H9A	0.1887	0.6056	0.1520	0.058*
H9B	0.0424	0.6370	0.2547	0.058*
C10	−0.1061 (5)	0.6530 (2)	0.0775 (3)	0.0485 (8)
H10A	−0.1667	0.7105	0.1092	0.058*
H10B	−0.0350	0.6689	0.0050	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0555 (14)	0.0359 (11)	0.0632 (14)	−0.0015 (10)	−0.0279 (11)	0.0039 (10)
O2	0.0654 (15)	0.0362 (12)	0.0725 (16)	−0.0084 (11)	−0.0270 (12)	0.0080 (11)
O3	0.0563 (14)	0.0466 (13)	0.0708 (16)	−0.0159 (11)	−0.0233 (11)	0.0138 (11)
N1	0.0419 (14)	0.0352 (13)	0.0486 (15)	−0.0065 (11)	−0.0158 (12)	0.0045 (11)
N2	0.0500 (16)	0.0446 (15)	0.0672 (18)	−0.0092 (13)	−0.0244 (13)	0.0170 (14)
C1	0.0399 (18)	0.0331 (16)	0.049 (2)	−0.0028 (14)	−0.0151 (14)	−0.0001 (14)
C2	0.051 (2)	0.056 (2)	0.061 (2)	0.0028 (17)	0.0024 (17)	0.0038 (17)
C3	0.049 (2)	0.060 (2)	0.086 (3)	0.0148 (18)	−0.004 (2)	0.000 (2)
C4	0.066 (3)	0.0436 (19)	0.071 (3)	0.0043 (18)	−0.031 (2)	−0.0014 (18)
C5	0.090 (3)	0.066 (2)	0.042 (2)	0.012 (2)	−0.0062 (19)	0.0011 (17)
C6	0.061 (2)	0.062 (2)	0.055 (2)	0.0177 (18)	−0.0006 (18)	−0.0086 (18)
C7	0.0403 (19)	0.0395 (18)	0.0445 (18)	−0.0019 (14)	−0.0057 (14)	0.0007 (15)
C8	0.0417 (18)	0.0405 (17)	0.0408 (18)	−0.0059 (15)	−0.0056 (14)	0.0023 (15)
C9	0.0441 (18)	0.0390 (17)	0.059 (2)	−0.0058 (14)	−0.0085 (15)	0.0052 (15)
C10	0.052 (2)	0.0391 (17)	0.052 (2)	−0.0029 (15)	−0.0087 (15)	0.0053 (15)

Geometric parameters (Å, º)

O1—C7	1.352 (3)	C2—H2A	0.9300
O1—C1	1.410 (3)	C3—C4	1.354 (4)
O2—C7	1.186 (3)	C3—H3	0.9300
O3—C8	1.217 (3)	C4—C5	1.362 (5)
N1—C7	1.378 (3)	C4—H4	0.9300
N1—C8	1.399 (4)	C5—C6	1.378 (4)
N1—C9	1.466 (3)	C5—H5	0.9300
N2—C8	1.321 (3)	C6—H6	0.9300
N2—C10	1.438 (3)	C9—C10	1.524 (4)
N2—H2	0.8600	C9—H9A	0.9700
C1—C2	1.355 (4)	C9—H9B	0.9700
C1—C6	1.361 (4)	C10—H10A	0.9700
C2—C3	1.383 (4)	C10—H10B	0.9700
C7—O1—C1	116.4 (2)	C1—C6—C5	118.9 (3)
C7—N1—C8	124.1 (2)	C1—C6—H6	120.6
C7—N1—C9	124.5 (2)	C5—C6—H6	120.6
C8—N1—C9	111.3 (2)	O2—C7—O1	125.1 (3)
C8—N2—C10	115.0 (2)	O2—C7—N1	127.0 (3)
C8—N2—H2	122.5	O1—C7—N1	107.9 (2)
C10—N2—H2	122.5	O3—C8—N2	127.9 (3)
C2—C1—C6	121.6 (3)	O3—C8—N1	125.1 (3)
C2—C1—O1	119.1 (3)	N2—C8—N1	107.1 (2)
C6—C1—O1	119.2 (3)	N1—C9—C10	103.0 (2)
C1—C2—C3	118.8 (3)	N1—C9—H9A	111.2
C1—C2—H2A	120.6	C10—C9—H9A	111.2
C3—C2—H2A	120.6	N1—C9—H9B	111.2
C4—C3—C2	120.5 (3)	C10—C9—H9B	111.2
C4—C3—H3	119.8	H9A—C9—H9B	109.1
C2—C3—H3	119.8	N2—C10—C9	103.2 (2)
C3—C4—C5	120.0 (3)	N2—C10—H10A	111.1
C3—C4—H4	120.0	C9—C10—H10A	111.1
C5—C4—H4	120.0	N2—C10—H10B	111.1
C4—C5—C6	120.3 (3)	C9—C10—H10B	111.1
C4—C5—H5	119.9	H10A—C10—H10B	109.1
C6—C5—H5	119.9
C7—O1—C1—C2	91.4 (3)	C9—N1—C7—O2	−171.3 (3)
C7—O1—C1—C6	−92.7 (3)	C8—N1—C7—O1	−168.2 (2)
C6—C1—C2—C3	0.3 (5)	C9—N1—C7—O1	8.4 (4)
O1—C1—C2—C3	176.1 (3)	C10—N2—C8—O3	−177.6 (3)
C1—C2—C3—C4	0.3 (5)	C10—N2—C8—N1	2.3 (4)
C2—C3—C4—C5	−0.9 (5)	C7—N1—C8—O3	−0.9 (5)
C3—C4—C5—C6	0.8 (5)	C9—N1—C8—O3	−177.9 (3)
C2—C1—C6—C5	−0.4 (5)	C7—N1—C8—N2	179.2 (3)
O1—C1—C6—C5	−176.2 (3)	C9—N1—C8—N2	2.2 (3)
C4—C5—C6—C1	−0.2 (5)	C7—N1—C9—C10	177.7 (3)
C1—O1—C7—O2	1.7 (4)	C8—N1—C9—C10	−5.4 (3)
C1—O1—C7—N1	−178.0 (2)	C8—N2—C10—C9	−5.6 (3)
C8—N1—C7—O2	12.1 (5)	N1—C9—C10—N2	6.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.86	2.04	2.872 (3)	161
C4—H4···O3^ii	0.93	2.62	3.218 (4)	123
C2—H2A···O3^iii	0.93	2.48	3.403 (4)	175
C10—H10B···O2^iv	0.97	2.83	3.690 (4)	148

Symmetry codes: (i) −x−1, −y+1, −z; (ii) x+1, −y+1/2, z+1/2; (iii) x+1, y, z; (iv) −x, −y+1, −z.