Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032394/fl2145sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032394/fl2145Isup2.hkl |
CCDC reference: 657689
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.003 Å
- R factor = 0.051
- wR factor = 0.140
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
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
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.
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.
Synthesis: Mu et al. (2006); Smith et al. (1958); Zetzsche et al. (1938). Geometry: Allen et al. (1987); Etter (1990).
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.
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. |
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) Å3 |
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 on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0705P)2] where P = (Fo2 + 2Fc2)/3 |
3345 reflections | (Δ/σ)max < 0.001 |
193 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
C17H18N2O2 | γ = 76.5805 (16)° |
Mr = 282.33 | V = 727.41 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.2562 (3) Å | Mo Kα radiation |
b = 9.5498 (3) Å | µ = 0.09 mm−1 |
c = 10.4583 (4) Å | T = 90 K |
α = 65.0882 (16)° | 0.30 × 0.30 × 0.10 mm |
β = 83.8718 (16)° |
Nonius KappaCCD diffractometer | 3345 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 1857 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.992 | Rint = 0.056 |
6620 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.140 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.27 e Å−3 |
3345 reflections | Δρmin = −0.23 e Å−3 |
193 parameters |
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 | ||
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* |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
Experimental details
Crystal data | |
Chemical formula | C17H18N2O2 |
Mr | 282.33 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 90 |
a, b, c (Å) | 8.2562 (3), 9.5498 (3), 10.4583 (4) |
α, β, γ (°) | 65.0882 (16), 83.8718 (16), 76.5805 (16) |
V (Å3) | 727.41 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.975, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6620, 3345, 1857 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.140, 0.97 |
No. of reflections | 3345 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.23 |
Computer programs: COLLECT (Nonius, 2002), SCALEPACK (Otwinowski & Minor, 1997), DENZO–SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1995), SHELXL97 and local procedures.
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.