organic compounds
of 1,3-dicyclohexyl-1-[3-(pyren-1-yl)propanoyl]urea
aCentro de Investigación en Ingeniería y Ciencias Aplicadas, Universidad Autónoma del Estado de Morelos, Av. Universidad No. 1001 Col. Chamilpa, CP 62209, Cuernavaca Mor., Mexico, and bCentro de Investigaciónes Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad No. 1001 Col. Chamilpa, CP 62209, Cuernavaca Mor., Mexico
*Correspondence e-mail: vbarba@uaem.mx
In the title compound, C33H38N2O2, each of the cyclohexyl rings adopts a chair conformation. The two planes involving carbonyl groups, C—(C=O)—N and N—(C=O)—N, are oriented at a dihedral angle of 62.28 (10)°. In the crystal, two neighboring molecules are linked by a pair of N—H⋯O interactions, generating an inversion dimer. The dimers are interconnected by C—H⋯O hydrogen bonds into a supramolecular chain along the a-axis direction.
Keywords: crystal structure; N,N′-dicyclohexylcarbodimide; N,N′-dicyclohexylurea; hydrogen bonds.
CCDC reference: 1420776
1. Related literature
For the synthesis of the title compound, see: Abd-El-Aziz et al. (2013). For the syntheses of N,N′-dicyclohexylcarbodiimide and N-acyl-N,N′-dicyclohexylurea, see: Zhu et al. (2008); Gonçalves & Balogh (2006); Kaiser et al. (2008); Slebioda (1995). For related crystal structures, see: Chérioux et al. (2002); Cai et al. (2009); Imhof (2007); Dhinaa et al. (2010); Pinheiro et al. (2011).
2. Experimental
2.1. Crystal data
|
2.3. Refinement
|
Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, DIAMOND (Brandenburg, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1420776
10.1107/S2056989015015996/is5410sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015015996/is5410Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015015996/is5410Isup3.cml
Compound I was obtained according to the literature (Abd-El-Aziz et al., 2013) from an incomplete esterification reaction between pyrenobutanoic acid (6.80 mmol), N,N'-dicyclohexylcarbodiimide (7.48 mmol), 2,6-dimethylpyridine (1.08 mmol) as catalyst and 2-(thiophene-3-yl) ethanol (13.6 mmol). The three first components were stirred under room temperature for 1.5 h using 40 ml of toluene, then the last component was added and heated 1 h under reflux. (I) was isolated in a yield ca 8% from a
using hexane-ethyl acetate system 4:1. From slow evaporation of the mixture solution, suitable crystals for X-ray diffraction were obtained (m.p. = 164 °C).H atoms were positioned geometrically [C—H = 0.95 Å (aryl), 0.99 Å (methylene) and 1.00 Å (methine)] and constrained using a riding-model approximation with Uiso(H) = 1.2Ueq(C). The H atom bonded to N (H2A) was located in a difference Fourier map and refined freely with an N—H distance restraint of 0.86 (1) Å.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), DIAMOND (Brandenburg, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A view of the crystal packing of the title compound. Hydrogen atoms not involved in the hydrogen bonds (dashed lines) have been omitted for clarity. |
C33H38N2O2 | Z = 2 |
Mr = 494.65 | F(000) = 532 |
Triclinic, P1 | Dx = 1.241 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0505 (15) Å | Cell parameters from 5456 reflections |
b = 10.1845 (17) Å | θ = 2.6–28.2° |
c = 14.571 (2) Å | µ = 0.08 mm−1 |
α = 99.541 (3)° | T = 100 K |
β = 90.315 (3)° | Plates, colourless |
γ = 92.191 (3)° | 0.16 × 0.13 × 0.11 mm |
V = 1323.4 (4) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 4658 independent reflections |
Radiation source: fine-focus sealed tube | 3738 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 8.3 pixels mm-1 | θmax = 25.0°, θmin = 1.4° |
phi and ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −12→12 |
Tmin = 0.988, Tmax = 0.992 | l = −17→17 |
12906 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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.031P)2 + 0.3784P] where P = (Fo2 + 2Fc2)/3 |
4658 reflections | (Δ/σ)max = 0.001 |
338 parameters | Δρmax = 0.19 e Å−3 |
1 restraint | Δρmin = −0.17 e Å−3 |
C33H38N2O2 | γ = 92.191 (3)° |
Mr = 494.65 | V = 1323.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.0505 (15) Å | Mo Kα radiation |
b = 10.1845 (17) Å | µ = 0.08 mm−1 |
c = 14.571 (2) Å | T = 100 K |
α = 99.541 (3)° | 0.16 × 0.13 × 0.11 mm |
β = 90.315 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 4658 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 3738 reflections with I > 2σ(I) |
Tmin = 0.988, Tmax = 0.992 | Rint = 0.050 |
12906 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 1 restraint |
wR(F2) = 0.128 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.19 e Å−3 |
4658 reflections | Δρmin = −0.17 e Å−3 |
338 parameters |
Experimental. 1H NMR (400 MHz, CDCl3) δ: 8.29 (d, J = 9.2 Hz, 2H), 8.15 (d, J = 7.8 Hz, 2H), 8.10 (dd, J = 7.7, 6.8 Hz, 2H), 8.0 (t, J= 7.7 Hz, 1H), 7.85 (d, J = 7.8 HZ, 2H), 5.27 (s, 1H), 3.90 (qn, J = 7.0 Hz, 2H), 3.36 (t, J =7.2 Hz, 2H), 2.38 (t, J = 7.2 Hz, 2H), 2.18 (qn, J = 7.2 Hz, 2H), 0.6–1.8 (m, 20H). IR (KBr) (cm-1) = 3299 (w), 2930 (m), 2859 (w), 1702 (s), 1633 (s), 1534 (m), 1365 (m), 1239(m), 835 (s). EI—MS m/z (%): 494 (M+, 5), 369 (50), 228 (100), 215 (45). |
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 | ||
C1 | 0.15199 (19) | 0.48523 (17) | 0.56198 (11) | 0.0247 (4) | |
C2 | 0.1888 (2) | 0.63158 (17) | 0.56245 (12) | 0.0265 (4) | |
H2C | 0.1232 | 0.6644 | 0.5173 | 0.032* | |
H2D | 0.2920 | 0.6421 | 0.5418 | 0.032* | |
C3 | 0.1715 (2) | 0.71654 (18) | 0.65839 (12) | 0.0295 (4) | |
H3A | 0.1728 | 0.8117 | 0.6516 | 0.035* | |
H3B | 0.0743 | 0.6941 | 0.6839 | 0.035* | |
C4 | 0.2932 (2) | 0.6959 (2) | 0.72692 (12) | 0.0351 (5) | |
H4A | 0.2843 | 0.6033 | 0.7394 | 0.042* | |
H4B | 0.3906 | 0.7079 | 0.6983 | 0.042* | |
C5 | 0.2863 (2) | 0.79106 (19) | 0.81785 (12) | 0.0322 (4) | |
C6 | 0.1854 (2) | 0.76932 (18) | 0.88786 (12) | 0.0292 (4) | |
C7 | 0.0873 (2) | 0.65401 (18) | 0.87947 (13) | 0.0336 (5) | |
H7 | 0.0897 | 0.5889 | 0.8247 | 0.040* | |
C8 | −0.0083 (2) | 0.63533 (19) | 0.94717 (13) | 0.0366 (5) | |
H8 | −0.0714 | 0.5575 | 0.9387 | 0.044* | |
C9 | −0.0176 (2) | 0.72924 (19) | 1.03139 (13) | 0.0348 (5) | |
C10 | −0.1161 (2) | 0.7118 (2) | 1.10233 (15) | 0.0450 (5) | |
H10 | −0.1796 | 0.6342 | 1.0956 | 0.054* | |
C11 | −0.1221 (3) | 0.8056 (2) | 1.18188 (15) | 0.0508 (6) | |
H11 | −0.1890 | 0.7918 | 1.2297 | 0.061* | |
C12 | −0.0319 (2) | 0.9196 (2) | 1.19279 (14) | 0.0440 (5) | |
H12 | −0.0386 | 0.9838 | 1.2478 | 0.053* | |
C13 | 0.0690 (2) | 0.94226 (19) | 1.12456 (12) | 0.0346 (5) | |
C14 | 0.1642 (2) | 1.0593 (2) | 1.13308 (13) | 0.0392 (5) | |
H14 | 0.1596 | 1.1249 | 1.1875 | 0.047* | |
C15 | 0.2598 (2) | 1.0785 (2) | 1.06597 (14) | 0.0381 (5) | |
H15 | 0.3211 | 1.1574 | 1.0739 | 0.046* | |
C16 | 0.2715 (2) | 0.98252 (18) | 0.98232 (13) | 0.0319 (4) | |
C17 | 0.3699 (2) | 1.0003 (2) | 0.91197 (13) | 0.0382 (5) | |
H17 | 0.4333 | 1.0780 | 0.9188 | 0.046* | |
C18 | 0.3764 (2) | 0.9061 (2) | 0.83215 (13) | 0.0383 (5) | |
H18 | 0.4449 | 0.9207 | 0.7854 | 0.046* | |
C19 | 0.1783 (2) | 0.86558 (18) | 0.97074 (12) | 0.0296 (4) | |
C20 | 0.0770 (2) | 0.84527 (18) | 1.04232 (12) | 0.0301 (4) | |
C21 | 0.20051 (19) | 0.25014 (17) | 0.50327 (12) | 0.0272 (4) | |
H21 | 0.1011 | 0.2347 | 0.5300 | 0.033* | |
C22 | 0.2051 (2) | 0.16123 (18) | 0.40814 (12) | 0.0329 (5) | |
H22A | 0.1279 | 0.1870 | 0.3669 | 0.040* | |
H22B | 0.3024 | 0.1735 | 0.3794 | 0.040* | |
C23 | 0.1795 (2) | 0.01573 (19) | 0.41794 (14) | 0.0376 (5) | |
H23A | 0.0779 | 0.0019 | 0.4402 | 0.045* | |
H23B | 0.1890 | −0.0409 | 0.3563 | 0.045* | |
C24 | 0.2896 (2) | −0.02592 (19) | 0.48565 (14) | 0.0396 (5) | |
H24A | 0.3900 | −0.0238 | 0.4592 | 0.048* | |
H24B | 0.2648 | −0.1186 | 0.4943 | 0.048* | |
C25 | 0.2887 (2) | 0.06563 (18) | 0.57992 (13) | 0.0374 (5) | |
H25A | 0.1922 | 0.0548 | 0.6100 | 0.045* | |
H25B | 0.3668 | 0.0398 | 0.6206 | 0.045* | |
C26 | 0.3151 (2) | 0.21121 (18) | 0.56959 (12) | 0.0305 (4) | |
H26A | 0.3083 | 0.2686 | 0.6312 | 0.037* | |
H26B | 0.4156 | 0.2244 | 0.5452 | 0.037* | |
C27 | 0.3174 (2) | 0.42850 (17) | 0.42681 (12) | 0.0264 (4) | |
C28 | 0.3480 (2) | 0.54841 (18) | 0.29600 (12) | 0.0290 (4) | |
H28 | 0.4519 | 0.5645 | 0.3200 | 0.035* | |
C29 | 0.3498 (2) | 0.44741 (19) | 0.20684 (12) | 0.0368 (5) | |
H29A | 0.2471 | 0.4248 | 0.1844 | 0.044* | |
H29B | 0.3940 | 0.3648 | 0.2197 | 0.044* | |
C30 | 0.4382 (3) | 0.5017 (2) | 0.13153 (15) | 0.0547 (6) | |
H30A | 0.5438 | 0.5123 | 0.1505 | 0.066* | |
H30B | 0.4303 | 0.4367 | 0.0729 | 0.066* | |
C31 | 0.3839 (3) | 0.6349 (2) | 0.11436 (14) | 0.0485 (6) | |
H31A | 0.4491 | 0.6700 | 0.0690 | 0.058* | |
H31B | 0.2828 | 0.6221 | 0.0872 | 0.058* | |
C32 | 0.3822 (3) | 0.7348 (2) | 0.20321 (14) | 0.0459 (5) | |
H32A | 0.3393 | 0.8181 | 0.1906 | 0.055* | |
H32B | 0.4848 | 0.7562 | 0.2263 | 0.055* | |
C33 | 0.2913 (3) | 0.6800 (2) | 0.27775 (14) | 0.0450 (6) | |
H33A | 0.2962 | 0.7454 | 0.3362 | 0.054* | |
H33B | 0.1866 | 0.6673 | 0.2572 | 0.054* | |
H2A | 0.1664 (11) | 0.5120 (18) | 0.3687 (12) | 0.028 (5)* | |
N1 | 0.21491 (16) | 0.39366 (14) | 0.49557 (10) | 0.0257 (3) | |
N2 | 0.25912 (17) | 0.49893 (15) | 0.36770 (10) | 0.0297 (4) | |
O1 | 0.06756 (13) | 0.44841 (12) | 0.61964 (8) | 0.0314 (3) | |
O2 | 0.44266 (14) | 0.38979 (13) | 0.42418 (9) | 0.0353 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0230 (9) | 0.0294 (10) | 0.0212 (9) | 0.0054 (7) | 0.0028 (7) | 0.0014 (8) |
C2 | 0.0285 (10) | 0.0267 (10) | 0.0242 (9) | 0.0052 (8) | 0.0049 (7) | 0.0023 (7) |
C3 | 0.0317 (10) | 0.0272 (10) | 0.0286 (10) | 0.0072 (8) | 0.0063 (8) | −0.0004 (8) |
C4 | 0.0336 (11) | 0.0422 (12) | 0.0277 (10) | 0.0115 (9) | 0.0044 (8) | −0.0015 (9) |
C5 | 0.0297 (10) | 0.0386 (11) | 0.0272 (10) | 0.0099 (9) | 0.0001 (8) | 0.0002 (8) |
C6 | 0.0317 (10) | 0.0283 (10) | 0.0269 (10) | 0.0085 (8) | −0.0017 (8) | 0.0013 (8) |
C7 | 0.0445 (12) | 0.0273 (10) | 0.0279 (10) | 0.0052 (9) | −0.0016 (9) | 0.0004 (8) |
C8 | 0.0429 (12) | 0.0308 (11) | 0.0366 (11) | −0.0016 (9) | −0.0027 (9) | 0.0076 (9) |
C9 | 0.0381 (11) | 0.0363 (11) | 0.0319 (11) | 0.0075 (9) | 0.0010 (9) | 0.0098 (9) |
C10 | 0.0472 (13) | 0.0451 (13) | 0.0462 (13) | 0.0027 (10) | 0.0095 (10) | 0.0167 (11) |
C11 | 0.0553 (15) | 0.0647 (16) | 0.0355 (12) | 0.0115 (12) | 0.0179 (11) | 0.0143 (11) |
C12 | 0.0501 (14) | 0.0526 (14) | 0.0292 (11) | 0.0161 (11) | 0.0081 (10) | 0.0029 (10) |
C13 | 0.0403 (12) | 0.0391 (12) | 0.0247 (10) | 0.0163 (9) | −0.0002 (8) | 0.0027 (8) |
C14 | 0.0487 (13) | 0.0371 (12) | 0.0285 (11) | 0.0123 (10) | −0.0054 (9) | −0.0064 (9) |
C15 | 0.0436 (12) | 0.0320 (11) | 0.0362 (11) | 0.0028 (9) | −0.0073 (9) | −0.0017 (9) |
C16 | 0.0314 (11) | 0.0331 (11) | 0.0301 (10) | 0.0037 (8) | −0.0035 (8) | 0.0014 (8) |
C17 | 0.0362 (11) | 0.0383 (12) | 0.0385 (11) | −0.0063 (9) | −0.0028 (9) | 0.0031 (9) |
C18 | 0.0318 (11) | 0.0506 (13) | 0.0314 (11) | 0.0012 (9) | 0.0052 (9) | 0.0036 (9) |
C19 | 0.0308 (10) | 0.0320 (10) | 0.0261 (10) | 0.0088 (8) | −0.0019 (8) | 0.0032 (8) |
C20 | 0.0335 (11) | 0.0332 (11) | 0.0247 (10) | 0.0108 (8) | 0.0000 (8) | 0.0054 (8) |
C21 | 0.0272 (10) | 0.0246 (9) | 0.0288 (10) | 0.0024 (7) | 0.0088 (8) | 0.0010 (8) |
C22 | 0.0364 (11) | 0.0321 (11) | 0.0288 (10) | 0.0077 (8) | −0.0003 (8) | −0.0010 (8) |
C23 | 0.0399 (12) | 0.0310 (11) | 0.0378 (11) | 0.0002 (9) | 0.0037 (9) | −0.0061 (9) |
C24 | 0.0507 (13) | 0.0260 (10) | 0.0418 (12) | 0.0043 (9) | 0.0041 (10) | 0.0038 (9) |
C25 | 0.0484 (13) | 0.0303 (11) | 0.0342 (11) | 0.0031 (9) | 0.0027 (9) | 0.0071 (9) |
C26 | 0.0361 (11) | 0.0294 (10) | 0.0254 (10) | 0.0012 (8) | 0.0039 (8) | 0.0024 (8) |
C27 | 0.0291 (10) | 0.0242 (9) | 0.0237 (9) | 0.0036 (8) | 0.0084 (8) | −0.0034 (7) |
C28 | 0.0310 (10) | 0.0320 (10) | 0.0238 (9) | 0.0017 (8) | 0.0088 (8) | 0.0039 (8) |
C29 | 0.0515 (13) | 0.0306 (11) | 0.0277 (10) | 0.0058 (9) | 0.0065 (9) | 0.0018 (8) |
C30 | 0.0814 (18) | 0.0509 (14) | 0.0338 (12) | 0.0183 (13) | 0.0249 (12) | 0.0081 (10) |
C31 | 0.0625 (15) | 0.0533 (14) | 0.0340 (12) | 0.0037 (11) | 0.0122 (10) | 0.0188 (10) |
C32 | 0.0595 (15) | 0.0352 (12) | 0.0458 (13) | 0.0034 (10) | 0.0098 (11) | 0.0140 (10) |
C33 | 0.0628 (15) | 0.0336 (12) | 0.0392 (12) | 0.0114 (10) | 0.0191 (11) | 0.0050 (9) |
N1 | 0.0285 (8) | 0.0238 (8) | 0.0245 (8) | 0.0048 (6) | 0.0091 (6) | 0.0018 (6) |
N2 | 0.0272 (9) | 0.0360 (9) | 0.0268 (8) | 0.0081 (7) | 0.0095 (7) | 0.0061 (7) |
O1 | 0.0335 (7) | 0.0323 (7) | 0.0280 (7) | 0.0041 (6) | 0.0136 (6) | 0.0023 (6) |
O2 | 0.0284 (7) | 0.0413 (8) | 0.0371 (8) | 0.0081 (6) | 0.0103 (6) | 0.0075 (6) |
C1—O1 | 1.2329 (19) | C21—N1 | 1.485 (2) |
C1—N1 | 1.370 (2) | C21—C26 | 1.521 (2) |
C1—C2 | 1.514 (2) | C21—C22 | 1.527 (2) |
C2—C3 | 1.529 (2) | C21—H21 | 1.0000 |
C2—H2C | 0.9900 | C22—C23 | 1.521 (3) |
C2—H2D | 0.9900 | C22—H22A | 0.9900 |
C3—C4 | 1.526 (3) | C22—H22B | 0.9900 |
C3—H3A | 0.9900 | C23—C24 | 1.518 (3) |
C3—H3B | 0.9900 | C23—H23A | 0.9900 |
C4—C5 | 1.510 (2) | C23—H23B | 0.9900 |
C4—H4A | 0.9900 | C24—C25 | 1.527 (3) |
C4—H4B | 0.9900 | C24—H24A | 0.9900 |
C5—C18 | 1.388 (3) | C24—H24B | 0.9900 |
C5—C6 | 1.412 (2) | C25—C26 | 1.525 (3) |
C6—C19 | 1.427 (2) | C25—H25A | 0.9900 |
C6—C7 | 1.433 (3) | C25—H25B | 0.9900 |
C7—C8 | 1.348 (3) | C26—H26A | 0.9900 |
C7—H7 | 0.9500 | C26—H26B | 0.9900 |
C8—C9 | 1.430 (3) | C27—O2 | 1.213 (2) |
C8—H8 | 0.9500 | C27—N2 | 1.328 (2) |
C9—C10 | 1.398 (3) | C27—N1 | 1.447 (2) |
C9—C20 | 1.419 (3) | C28—N2 | 1.464 (2) |
C10—C11 | 1.378 (3) | C28—C33 | 1.516 (3) |
C10—H10 | 0.9500 | C28—C29 | 1.518 (2) |
C11—C12 | 1.380 (3) | C28—H28 | 1.0000 |
C11—H11 | 0.9500 | C29—C30 | 1.525 (3) |
C12—C13 | 1.394 (3) | C29—H29A | 0.9900 |
C12—H12 | 0.9500 | C29—H29B | 0.9900 |
C13—C20 | 1.425 (2) | C30—C31 | 1.520 (3) |
C13—C14 | 1.432 (3) | C30—H30A | 0.9900 |
C14—C15 | 1.343 (3) | C30—H30B | 0.9900 |
C14—H14 | 0.9500 | C31—C32 | 1.509 (3) |
C15—C16 | 1.438 (3) | C31—H31A | 0.9900 |
C15—H15 | 0.9500 | C31—H31B | 0.9900 |
C16—C17 | 1.391 (3) | C32—C33 | 1.531 (3) |
C16—C19 | 1.419 (3) | C32—H32A | 0.9900 |
C17—C18 | 1.382 (3) | C32—H32B | 0.9900 |
C17—H17 | 0.9500 | C33—H33A | 0.9900 |
C18—H18 | 0.9500 | C33—H33B | 0.9900 |
C19—C20 | 1.428 (2) | N2—H2A | 0.855 (9) |
O1—C1—N1 | 120.38 (16) | C23—C22—C21 | 110.36 (15) |
O1—C1—C2 | 121.25 (14) | C23—C22—H22A | 109.6 |
N1—C1—C2 | 118.37 (14) | C21—C22—H22A | 109.6 |
C1—C2—C3 | 112.77 (14) | C23—C22—H22B | 109.6 |
C1—C2—H2C | 109.0 | C21—C22—H22B | 109.6 |
C3—C2—H2C | 109.0 | H22A—C22—H22B | 108.1 |
C1—C2—H2D | 109.0 | C24—C23—C22 | 111.45 (16) |
C3—C2—H2D | 109.0 | C24—C23—H23A | 109.3 |
H2C—C2—H2D | 107.8 | C22—C23—H23A | 109.3 |
C4—C3—C2 | 112.71 (14) | C24—C23—H23B | 109.3 |
C4—C3—H3A | 109.0 | C22—C23—H23B | 109.3 |
C2—C3—H3A | 109.0 | H23A—C23—H23B | 108.0 |
C4—C3—H3B | 109.0 | C23—C24—C25 | 111.59 (16) |
C2—C3—H3B | 109.0 | C23—C24—H24A | 109.3 |
H3A—C3—H3B | 107.8 | C25—C24—H24A | 109.3 |
C5—C4—C3 | 112.66 (15) | C23—C24—H24B | 109.3 |
C5—C4—H4A | 109.1 | C25—C24—H24B | 109.3 |
C3—C4—H4A | 109.1 | H24A—C24—H24B | 108.0 |
C5—C4—H4B | 109.1 | C26—C25—C24 | 111.40 (15) |
C3—C4—H4B | 109.1 | C26—C25—H25A | 109.3 |
H4A—C4—H4B | 107.8 | C24—C25—H25A | 109.3 |
C18—C5—C6 | 118.59 (16) | C26—C25—H25B | 109.3 |
C18—C5—C4 | 119.68 (17) | C24—C25—H25B | 109.3 |
C6—C5—C4 | 121.66 (17) | H25A—C25—H25B | 108.0 |
C5—C6—C19 | 119.51 (17) | C21—C26—C25 | 109.86 (15) |
C5—C6—C7 | 122.80 (16) | C21—C26—H26A | 109.7 |
C19—C6—C7 | 117.69 (16) | C25—C26—H26A | 109.7 |
C8—C7—C6 | 121.81 (17) | C21—C26—H26B | 109.7 |
C8—C7—H7 | 119.1 | C25—C26—H26B | 109.7 |
C6—C7—H7 | 119.1 | H26A—C26—H26B | 108.2 |
C7—C8—C9 | 121.97 (18) | O2—C27—N2 | 125.42 (16) |
C7—C8—H8 | 119.0 | O2—C27—N1 | 120.55 (16) |
C9—C8—H8 | 119.0 | N2—C27—N1 | 113.96 (15) |
C10—C9—C20 | 119.10 (18) | N2—C28—C33 | 110.08 (14) |
C10—C9—C8 | 122.84 (19) | N2—C28—C29 | 111.64 (15) |
C20—C9—C8 | 118.06 (17) | C33—C28—C29 | 110.95 (16) |
C11—C10—C9 | 120.8 (2) | N2—C28—H28 | 108.0 |
C11—C10—H10 | 119.6 | C33—C28—H28 | 108.0 |
C9—C10—H10 | 119.6 | C29—C28—H28 | 108.0 |
C10—C11—C12 | 120.65 (19) | C28—C29—C30 | 111.25 (16) |
C10—C11—H11 | 119.7 | C28—C29—H29A | 109.4 |
C12—C11—H11 | 119.7 | C30—C29—H29A | 109.4 |
C11—C12—C13 | 121.16 (19) | C28—C29—H29B | 109.4 |
C11—C12—H12 | 119.4 | C30—C29—H29B | 109.4 |
C13—C12—H12 | 119.4 | H29A—C29—H29B | 108.0 |
C12—C13—C20 | 118.67 (19) | C31—C30—C29 | 111.98 (17) |
C12—C13—C14 | 122.89 (18) | C31—C30—H30A | 109.2 |
C20—C13—C14 | 118.43 (17) | C29—C30—H30A | 109.2 |
C15—C14—C13 | 121.50 (18) | C31—C30—H30B | 109.2 |
C15—C14—H14 | 119.2 | C29—C30—H30B | 109.2 |
C13—C14—H14 | 119.2 | H30A—C30—H30B | 107.9 |
C14—C15—C16 | 121.61 (19) | C32—C31—C30 | 111.46 (17) |
C14—C15—H15 | 119.2 | C32—C31—H31A | 109.3 |
C16—C15—H15 | 119.2 | C30—C31—H31A | 109.3 |
C17—C16—C19 | 118.72 (16) | C32—C31—H31B | 109.3 |
C17—C16—C15 | 122.57 (18) | C30—C31—H31B | 109.3 |
C19—C16—C15 | 118.71 (17) | H31A—C31—H31B | 108.0 |
C18—C17—C16 | 120.66 (18) | C31—C32—C33 | 110.94 (17) |
C18—C17—H17 | 119.7 | C31—C32—H32A | 109.5 |
C16—C17—H17 | 119.7 | C33—C32—H32A | 109.5 |
C17—C18—C5 | 122.37 (18) | C31—C32—H32B | 109.5 |
C17—C18—H18 | 118.8 | C33—C32—H32B | 109.5 |
C5—C18—H18 | 118.8 | H32A—C32—H32B | 108.0 |
C16—C19—C6 | 120.14 (16) | C28—C33—C32 | 111.45 (16) |
C16—C19—C20 | 119.56 (16) | C28—C33—H33A | 109.3 |
C6—C19—C20 | 120.30 (17) | C32—C33—H33A | 109.3 |
C9—C20—C13 | 119.65 (17) | C28—C33—H33B | 109.3 |
C9—C20—C19 | 120.16 (16) | C32—C33—H33B | 109.3 |
C13—C20—C19 | 120.18 (18) | H33A—C33—H33B | 108.0 |
N1—C21—C26 | 112.10 (14) | C1—N1—C27 | 123.78 (14) |
N1—C21—C22 | 111.76 (14) | C1—N1—C21 | 119.09 (14) |
C26—C21—C22 | 111.18 (14) | C27—N1—C21 | 116.20 (13) |
N1—C21—H21 | 107.2 | C27—N2—C28 | 121.70 (15) |
C26—C21—H21 | 107.2 | C27—N2—H2A | 119.8 (12) |
C22—C21—H21 | 107.2 | C28—N2—H2A | 118.4 (12) |
O1—C1—C2—C3 | 25.2 (2) | C8—C9—C20—C19 | −0.3 (3) |
N1—C1—C2—C3 | −154.78 (15) | C12—C13—C20—C9 | 0.5 (3) |
C1—C2—C3—C4 | 72.4 (2) | C14—C13—C20—C9 | −179.06 (17) |
C2—C3—C4—C5 | 173.33 (16) | C12—C13—C20—C19 | 179.60 (16) |
C3—C4—C5—C18 | −97.4 (2) | C14—C13—C20—C19 | 0.1 (3) |
C3—C4—C5—C6 | 79.7 (2) | C16—C19—C20—C9 | 179.55 (16) |
C18—C5—C6—C19 | 0.2 (3) | C6—C19—C20—C9 | −0.2 (3) |
C4—C5—C6—C19 | −176.96 (16) | C16—C19—C20—C13 | 0.4 (3) |
C18—C5—C6—C7 | 179.69 (17) | C6—C19—C20—C13 | −179.31 (16) |
C4—C5—C6—C7 | 2.5 (3) | N1—C21—C22—C23 | −176.13 (15) |
C5—C6—C7—C8 | −179.91 (17) | C26—C21—C22—C23 | 57.8 (2) |
C19—C6—C7—C8 | −0.4 (3) | C21—C22—C23—C24 | −55.6 (2) |
C6—C7—C8—C9 | 0.0 (3) | C22—C23—C24—C25 | 54.4 (2) |
C7—C8—C9—C10 | 179.94 (18) | C23—C24—C25—C26 | −54.8 (2) |
C7—C8—C9—C20 | 0.4 (3) | N1—C21—C26—C25 | 176.17 (14) |
C20—C9—C10—C11 | 0.2 (3) | C22—C21—C26—C25 | −57.92 (19) |
C8—C9—C10—C11 | −179.37 (19) | C24—C25—C26—C21 | 56.1 (2) |
C9—C10—C11—C12 | 0.6 (3) | N2—C28—C29—C30 | 178.07 (16) |
C10—C11—C12—C13 | −0.9 (3) | C33—C28—C29—C30 | 54.9 (2) |
C11—C12—C13—C20 | 0.3 (3) | C28—C29—C30—C31 | −54.2 (3) |
C11—C12—C13—C14 | 179.83 (19) | C29—C30—C31—C32 | 54.4 (3) |
C12—C13—C14—C15 | −179.73 (19) | C30—C31—C32—C33 | −54.9 (3) |
C20—C13—C14—C15 | −0.2 (3) | N2—C28—C33—C32 | 179.84 (17) |
C13—C14—C15—C16 | −0.1 (3) | C29—C28—C33—C32 | −56.1 (2) |
C14—C15—C16—C17 | −179.91 (18) | C31—C32—C33—C28 | 56.2 (2) |
C14—C15—C16—C19 | 0.6 (3) | O1—C1—N1—C27 | −178.60 (15) |
C19—C16—C17—C18 | 0.2 (3) | C2—C1—N1—C27 | 1.4 (2) |
C15—C16—C17—C18 | −179.24 (18) | O1—C1—N1—C21 | −10.1 (2) |
C16—C17—C18—C5 | 0.3 (3) | C2—C1—N1—C21 | 169.94 (15) |
C6—C5—C18—C17 | −0.5 (3) | O2—C27—N1—C1 | 118.43 (19) |
C4—C5—C18—C17 | 176.71 (18) | N2—C27—N1—C1 | −64.3 (2) |
C17—C16—C19—C6 | −0.5 (3) | O2—C27—N1—C21 | −50.4 (2) |
C15—C16—C19—C6 | 178.97 (16) | N2—C27—N1—C21 | 126.88 (16) |
C17—C16—C19—C20 | 179.76 (17) | C26—C21—N1—C1 | −82.44 (19) |
C15—C16—C19—C20 | −0.7 (3) | C22—C21—N1—C1 | 151.97 (15) |
C5—C6—C19—C16 | 0.3 (3) | C26—C21—N1—C27 | 86.94 (18) |
C7—C6—C19—C16 | −179.21 (16) | C22—C21—N1—C27 | −38.7 (2) |
C5—C6—C19—C20 | −179.97 (16) | O2—C27—N2—C28 | −5.7 (3) |
C7—C6—C19—C20 | 0.5 (2) | N1—C27—N2—C28 | 177.15 (14) |
C10—C9—C20—C13 | −0.7 (3) | C33—C28—N2—C27 | −147.59 (18) |
C8—C9—C20—C13 | 178.86 (17) | C29—C28—N2—C27 | 88.7 (2) |
C10—C9—C20—C19 | −179.85 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.86 (1) | 2.17 (1) | 3.026 (2) | 176 (2) |
C2—H2D···O2ii | 0.99 | 2.49 | 3.358 (2) | 146 |
C4—H4B···O2ii | 0.99 | 2.45 | 3.302 (2) | 144 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.855 (10) | 2.173 (10) | 3.026 (2) | 176.4 (15) |
C2—H2D···O2ii | 0.99 | 2.49 | 3.358 (2) | 146 |
C4—H4B···O2ii | 0.99 | 2.45 | 3.302 (2) | 144 |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
Finantial support from CONACYT (grant No. CB2007–81383-Q) and for a scholarship to EGJ (grant No. 132946) is gratefully acknowledged.
References
Abd-El-Aziz, A. S., Dalgakiran, S., Kucukkaya, I. & Wagner, B. D. (2013). Electrochim. Acta, 89, 445–453. CAS Google Scholar
Brandenburg, K. (1997). DIAMOND. University of Bonn, Germany. Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cai, X.-Q., Yan, X.-W. & Xie, X.-N. (2009). Z. Kristallogr. New Cryst. Struct. 224, 211–212. CAS Google Scholar
Chérioux, F., Therrien, B., Stoeckli-Evans, H. & Süss-Fink, G. (2002). Acta Cryst. E58, o27–o29. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dhinaa, A. N., Jagan, R., Sivakumar, K. & Chinnakali, K. (2010). Acta Cryst. E66, o1291. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gonçalves, V. C. & Balogh, D. T. (2006). Eur. Polym. J. 42, 3303–3310. Google Scholar
Imhof, W. (2007). Acta Cryst. E63, o4036–o4037. CSD CrossRef IUCr Journals Google Scholar
Kaiser, C. R., Pinheiro, A. C., de Souza, M. V. N., Wardell, J. L. & Wardell, S. M. S. V. (2008). J. Chem. Res. (S), pp. 468–472. CrossRef Google Scholar
Pinheiro, A. C., Souza, M. V. N. de, Wardell, J. L., Wardell, S. M. S. V. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2676–o2677. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ślebioda, M. (1995). Tetrahedron, 51, 7829–7834. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhu, L., Zhu, Y., Meng, X., Hao, J., Li, Q., Wei, Y. & Lin, Y. (2008). Chem. Eur. J. 14, 10923–10927. CSD CrossRef PubMed CAS Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
N,N'-Dicyclohexylcarbodiimide has been used to form esters from carboxylic acid, alcohols and catalytic amounts of 2,6-dimethylpyridine (Zhu et al., 2008; Gonçalves & Balogh, 2006). Nonetheless, the absence of alcohols produce the formation of N-acyl-N,N'-dicyclohexylureas (Kaiser et al., 2008). When arenecarboxylic acids are used, the yield reaction can be modulated by electronic effects of the substituents (Slebioda, 1995). Several crystal structures of N-(arenecarbonyl)-N,N'-dicyclohexylurea derivatives have been reported (Chérioux et al., 2002; Cai et al., 2009; Imhof 2007; Dhinaa et al., 2010; Pinheiro et al., 2011). Herein, we now report the crystal structure of 1,3-dicyclohexyl-1-[(1-pyrenepropyl)carbonyl]urea (I).
In the molecular structure of I, the pyrenyl group and the two planes involving urea nitrogen atoms N1 and N2, C27/N1/C21/C1 and C28/N2/C27/H2A, are almost planar with r.m.s. deviations of 0.008 (2), 0.0346 (18) and 0.0098 (18) Å, respectively. The interplanar angle between the C27/N1/C21/C1 and C28/N2/C27/H2A planes is 61.1 (6)°. Each of the cyclohexyl rings adopts a chair conformation (Fig. 1). In the crystal, two neighboring molecules are linked by a pair of N—H···O interactions, generating an inversion dimer. The dimers are interconnected by C—H···O hydrogen bonds into a supramolecular chain along the a axis (Fig. 2 and Table 1).