N-p-Tolyl-N-[N-(p-tol­yl)carbamo­yl]­acetamide

The title compound, C₁₇H₁₈N₂O₂, was obtained by reacting N,N'-diphenyl-1H-imidazole-1-carboximidamide with tert-butyl acetate. There is an intra­molecular S(6) hydrogen-bonded loop formed between the urea NH group and the acetyl O atom. While the other potential hydrogen-bond acceptor, the carbonyl O atom of urea, does not participate in any hydrogen bonds, there are short contacts between each mol­ecule and four adjacent mol­ecules, indicating that they contribute to the stabilization of the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.051
• wR factor = 0.140
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

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Alert level C
CRYSC01_ALERT_1_C The word below has not been recognised as a standard
            identifier.
            block
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        160 Deg.

   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

   5 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

N-acetylureas, including N-p-tolyl-N-(p-tolylcarbamoyl)acetamide (I), were first synthesized by reacting AcOH with carbodiimides (Zetzsche et al., 1938; Smith et al., 1958). In 2006, a new method to prepare N-acetylureas was reported by Mu et al. (2006).The structures of two N-acetylureas including the title compound were confirmed by X-ray crystallography analysis, but no details of the structures were given. Here, we report the crystal structure of I obtained by a different synthesis method.

The asymmetric unit of (I), (Fig. 1), contains one molecule and the bond lengths and angles are within normal ranges (Allen et al., 1987). In the crystal structure, an S(6) hydrogen bond forms between the urea NH and the O of the acetyl group (Etter, 1990). The other hydrogen bond acceptor, the carbonyl O of the urea, does not participate in hydrogen bonds. Although no intermolecular hydrogen bonds are discovered in the crystal structure, short contacts exist between molecules. Each molecule is in short contact with four adjacent molecules, suggesting that weak interactions stablize the crystal structure.

Related literature

Synthesis: Mu et al. (2006); Smith et al. (1958); Zetzsche et al. (1938). Geometry: Allen et al. (1987); Etter (1990).

S2. Experimental

A saturated solution was prepared by dissolving 20 mg of N,N'-diphenyl-1H-imidazole-1-carboximidamide in 5 ml of tert-butyl acetate at room temperature. The resulted solution was set for crystal growth by slow evaporation. Single crystals of the title compound were obtained in a week.

Computing details

Data collection: COLLECT (Nonius, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO–SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local procedures.

Figures

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A packing diagram of (I) viewed along the a axis.

N-p-Tolyl-N-[N-(p-tolyl)carbamoyl]acetamide

Crystal data

C17H18N2O2	Z = 2
Mr = 282.33	F(000) = 300
Triclinic, P1	Dx = 1.289 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2562 (3) Å	Cell parameters from 3311 reflections
b = 9.5498 (3) Å	θ = 1–27.5°
c = 10.4583 (4) Å	µ = 0.09 mm^−1
α = 65.0882 (16)°	T = 90 K
β = 83.8718 (16)°	Colourless, block
γ = 76.5805 (16)°	0.30 × 0.30 × 0.10 mm
V = 727.41 (4) Å^3

Data collection

Nonius KappaCCD diffractometer	3345 independent reflections
Radiation source: fine-focus sealed tube	1857 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
Detector resolution: 18 pixels mm^-1	θmax = 27.5°, θmin = 2.2°
ω scans at fixed χ = 55°	h = −10→10
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997)	k = −12→12
Tmin = 0.975, Tmax = 0.992	l = −13→13
6620 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H-atom parameters constrained
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0705P)^2] where P = (Fo^2 + 2Fc^2)/3
3345 reflections	(Δ/σ)max < 0.001
193 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.23 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
N1	0.46825 (18)	0.80888 (17)	0.72922 (15)	0.0237 (4)
N2	0.73670 (18)	0.70652 (17)	0.66213 (15)	0.0261 (4)
H2	0.6883	0.7319	0.5821	0.031*
O1	0.68725 (16)	0.70943 (16)	0.87994 (14)	0.0378 (4)
O2	0.47319 (15)	0.83026 (14)	0.50216 (12)	0.0289 (3)
C1	0.6403 (2)	0.7371 (2)	0.76391 (19)	0.0259 (4)
C2	0.3756 (2)	0.8486 (2)	0.84037 (18)	0.0241 (4)
C3	0.2991 (2)	0.7396 (2)	0.94701 (18)	0.0291 (5)
H3	0.3013	0.6400	0.9463	0.035*
C4	0.2186 (2)	0.7773 (2)	1.05552 (18)	0.0306 (5)
H4	0.1646	0.7030	1.1284	0.037*
C5	0.2156 (2)	0.9213 (2)	1.05963 (18)	0.0277 (5)
C6	0.2924 (2)	1.0291 (2)	0.95016 (19)	0.0302 (5)
H6	0.2905	1.1288	0.9504	0.036*
C7	0.3719 (2)	0.9935 (2)	0.84048 (18)	0.0286 (5)
H7	0.4234	1.0687	0.7660	0.034*
C8	0.1338 (2)	0.9583 (2)	1.18071 (18)	0.0360 (5)
H8A	0.2054	0.9007	1.2636	0.054*
H8B	0.0260	0.9264	1.2026	0.054*
H8C	0.1168	1.0720	1.1547	0.054*
C9	0.9093 (2)	0.6371 (2)	0.67291 (18)	0.0244 (4)
C10	0.9928 (2)	0.5569 (2)	0.79996 (19)	0.0296 (5)
H10	0.9353	0.5492	0.8856	0.035*
C11	1.1606 (2)	0.4881 (2)	0.80180 (19)	0.0280 (5)
H11	1.2159	0.4325	0.8898	0.034*
C12	1.2499 (2)	0.4976 (2)	0.68017 (19)	0.0269 (4)
C13	1.1649 (2)	0.5796 (2)	0.55315 (19)	0.0287 (5)
H13	1.2233	0.5888	0.4676	0.034*
C14	0.9967 (2)	0.6482 (2)	0.54892 (19)	0.0279 (4)
H14	0.9411	0.7029	0.4611	0.033*
C15	1.4328 (2)	0.4226 (2)	0.6862 (2)	0.0332 (5)
H15A	1.4985	0.5049	0.6534	0.050*
H15B	1.4559	0.3650	0.6257	0.050*
H15C	1.4627	0.3493	0.7836	0.050*
C16	0.3945 (2)	0.85026 (19)	0.60228 (18)	0.0243 (4)
C17	0.2113 (2)	0.9195 (2)	0.59209 (19)	0.0298 (5)
H17A	0.1730	0.9457	0.4976	0.045*
H17B	0.1897	1.0153	0.6095	0.045*
H17C	0.1515	0.8426	0.6625	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0216 (9)	0.0285 (9)	0.0222 (8)	−0.0046 (7)	0.0026 (7)	−0.0125 (7)
N2	0.0225 (9)	0.0343 (9)	0.0241 (8)	−0.0055 (7)	0.0021 (7)	−0.0152 (7)
O1	0.0325 (8)	0.0508 (9)	0.0318 (8)	0.0018 (7)	−0.0031 (6)	−0.0233 (7)
O2	0.0289 (8)	0.0339 (8)	0.0248 (7)	−0.0057 (6)	0.0046 (6)	−0.0146 (6)
C1	0.0251 (11)	0.0275 (10)	0.0274 (10)	−0.0086 (8)	0.0040 (8)	−0.0130 (9)
C2	0.0217 (10)	0.0298 (10)	0.0221 (10)	−0.0040 (8)	0.0035 (8)	−0.0133 (8)
C3	0.0295 (11)	0.0296 (11)	0.0313 (11)	−0.0098 (9)	0.0029 (9)	−0.0145 (9)
C4	0.0296 (11)	0.0362 (12)	0.0236 (10)	−0.0114 (9)	0.0056 (9)	−0.0090 (9)
C5	0.0219 (10)	0.0343 (11)	0.0267 (10)	−0.0036 (8)	0.0025 (8)	−0.0142 (9)
C6	0.0354 (12)	0.0277 (11)	0.0306 (11)	−0.0057 (9)	0.0042 (9)	−0.0162 (9)
C7	0.0320 (11)	0.0274 (11)	0.0252 (10)	−0.0080 (9)	0.0048 (8)	−0.0099 (9)
C8	0.0330 (12)	0.0450 (13)	0.0291 (11)	−0.0044 (10)	0.0056 (9)	−0.0175 (10)
C9	0.0220 (10)	0.0224 (10)	0.0299 (11)	−0.0043 (8)	0.0019 (8)	−0.0126 (8)
C10	0.0306 (12)	0.0288 (11)	0.0291 (11)	−0.0065 (9)	0.0045 (9)	−0.0125 (9)
C11	0.0284 (11)	0.0264 (10)	0.0283 (10)	−0.0038 (9)	−0.0025 (9)	−0.0108 (9)
C12	0.0258 (11)	0.0219 (10)	0.0345 (11)	−0.0057 (8)	0.0031 (9)	−0.0133 (9)
C13	0.0277 (11)	0.0292 (11)	0.0290 (11)	−0.0064 (9)	0.0071 (9)	−0.0132 (9)
C14	0.0281 (11)	0.0281 (10)	0.0268 (10)	−0.0045 (9)	0.0016 (8)	−0.0118 (9)
C15	0.0296 (12)	0.0304 (11)	0.0374 (12)	−0.0046 (9)	0.0032 (9)	−0.0135 (9)
C16	0.0289 (11)	0.0204 (10)	0.0242 (10)	−0.0085 (8)	0.0026 (8)	−0.0088 (8)
C17	0.0285 (11)	0.0316 (11)	0.0282 (10)	−0.0023 (9)	−0.0001 (8)	−0.0135 (9)

Geometric parameters (Å, º)

N1—C16	1.381 (2)	C8—H8B	0.9800
N1—C1	1.438 (2)	C8—H8C	0.9800
N1—C2	1.458 (2)	C9—C10	1.386 (2)
N2—C1	1.351 (2)	C9—C14	1.390 (2)
N2—C9	1.420 (2)	C10—C11	1.387 (3)
N2—H2	0.8800	C10—H10	0.9500
O1—C1	1.215 (2)	C11—C12	1.380 (2)
O2—C16	1.233 (2)	C11—H11	0.9500
C2—C7	1.378 (2)	C12—C13	1.392 (2)
C2—C3	1.380 (2)	C12—C15	1.508 (2)
C3—C4	1.390 (2)	C13—C14	1.388 (3)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.388 (2)	C14—H14	0.9500
C4—H4	0.9500	C15—H15A	0.9800
C5—C6	1.389 (2)	C15—H15B	0.9800
C5—C8	1.506 (2)	C15—H15C	0.9800
C6—C7	1.387 (2)	C16—C17	1.499 (2)
C6—H6	0.9500	C17—H17A	0.9800
C7—H7	0.9500	C17—H17B	0.9800
C8—H8A	0.9800	C17—H17C	0.9800
C16—N1—C1	126.12 (14)	C10—C9—C14	118.99 (16)
C16—N1—C2	120.99 (14)	C10—C9—N2	123.41 (16)
C1—N1—C2	112.70 (13)	C14—C9—N2	117.59 (16)
C1—N2—C9	125.73 (16)	C9—C10—C11	119.83 (17)
C1—N2—H2	117.1	C9—C10—H10	120.1
C9—N2—H2	117.1	C11—C10—H10	120.1
O1—C1—N2	125.47 (17)	C12—C11—C10	122.23 (17)
O1—C1—N1	118.43 (15)	C12—C11—H11	118.9
N2—C1—N1	116.09 (16)	C10—C11—H11	118.9
C7—C2—C3	120.65 (16)	C11—C12—C13	117.36 (16)
C7—C2—N1	119.03 (15)	C11—C12—C15	120.70 (17)
C3—C2—N1	120.27 (15)	C13—C12—C15	121.94 (17)
C2—C3—C4	119.17 (17)	C14—C13—C12	121.40 (17)
C2—C3—H3	120.4	C14—C13—H13	119.3
C4—C3—H3	120.4	C12—C13—H13	119.3
C5—C4—C3	121.39 (17)	C13—C14—C9	120.19 (18)
C5—C4—H4	119.3	C13—C14—H14	119.9
C3—C4—H4	119.3	C9—C14—H14	119.9
C4—C5—C6	118.11 (16)	C12—C15—H15A	109.5
C4—C5—C8	120.90 (17)	C12—C15—H15B	109.5
C6—C5—C8	120.97 (17)	H15A—C15—H15B	109.5
C7—C6—C5	121.11 (17)	C12—C15—H15C	109.5
C7—C6—H6	119.4	H15A—C15—H15C	109.5
C5—C6—H6	119.4	H15B—C15—H15C	109.5
C2—C7—C6	119.56 (17)	O2—C16—N1	122.47 (16)
C2—C7—H7	120.2	O2—C16—C17	120.98 (16)
C6—C7—H7	120.2	N1—C16—C17	116.54 (15)
C5—C8—H8A	109.5	C16—C17—H17A	109.5
C5—C8—H8B	109.5	C16—C17—H17B	109.5
H8A—C8—H8B	109.5	H17A—C17—H17B	109.5
C5—C8—H8C	109.5	C16—C17—H17C	109.5
H8A—C8—H8C	109.5	H17A—C17—H17C	109.5
H8B—C8—H8C	109.5	H17B—C17—H17C	109.5
C9—N2—C1—O1	−0.1 (3)	N1—C2—C7—C6	−176.25 (16)
C9—N2—C1—N1	179.67 (15)	C5—C6—C7—C2	−0.4 (3)
C16—N1—C1—O1	179.03 (16)	C1—N2—C9—C10	16.3 (3)
C2—N1—C1—O1	4.0 (2)	C1—N2—C9—C14	−165.16 (16)
C16—N1—C1—N2	−0.7 (2)	C14—C9—C10—C11	−0.6 (3)
C2—N1—C1—N2	−175.77 (14)	N2—C9—C10—C11	177.90 (15)
C16—N1—C2—C7	−87.1 (2)	C9—C10—C11—C12	0.7 (3)
C1—N1—C2—C7	88.2 (2)	C10—C11—C12—C13	−0.1 (3)
C16—N1—C2—C3	95.6 (2)	C10—C11—C12—C15	179.34 (16)
C1—N1—C2—C3	−89.01 (19)	C11—C12—C13—C14	−0.4 (3)
C7—C2—C3—C4	−0.4 (3)	C15—C12—C13—C14	−179.92 (16)
N1—C2—C3—C4	176.79 (15)	C12—C13—C14—C9	0.5 (3)
C2—C3—C4—C5	−0.8 (3)	C10—C9—C14—C13	0.0 (3)
C3—C4—C5—C6	1.4 (3)	N2—C9—C14—C13	−178.57 (16)
C3—C4—C5—C8	−177.59 (17)	C1—N1—C16—O2	−0.9 (3)
C4—C5—C6—C7	−0.8 (3)	C2—N1—C16—O2	173.77 (15)
C8—C5—C6—C7	178.18 (17)	C1—N1—C16—C17	178.22 (15)
C3—C2—C7—C6	1.0 (3)	C2—N1—C16—C17	−7.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88	1.90	2.6167 (19)	137