organic compounds
2-[(Phenylcarbamoyl)amino]butyl N-phenylcarbamate
aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, b'Vinča' Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, PO Box 522, 11001 Belgrade, Serbia, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and dSchool Department of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title compound, C18H21N3O3, the terminal phenyl rings make a dihedral angle of 86.3 (5)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along [001], forming parallel C(4) and R12(6) graph-set motifs.
Related literature
For pharmaceutical properties of et al. (2009); Gisbert & Pajares (2004); Metcalf (2002); Ray & Chaturvedi (2004). For a related structure, see: Ghalib et al. (2010). For graph-set motifs, see: Bernstein et al. (1995).
and carbamide compounds, see: LiExperimental
Crystal data
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Data collection
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON.
Supporting information
https://doi.org/10.1107/S1600536812038081/hg5248sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038081/hg5248Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812038081/hg5248Isup3.cml
The title compound was obtained as a biproduct from a reaction mixture of 89 mg (1 mmol) 2-aminobutan-1-ol, 119 mg (1 mmol) phenylisocyanate and 93 mg (1 mmol) chloroacetone in 50 ml e thanol in presence of few drops of TEA. The reaction mixture was refluxed for 4 h then left to cool at ambient temperature. The solid that formed was decanted washed by ethanol and dried by filteration then recrystallized from acetone. M,p. 427 K. Colourless crystals suitable for X-ray diffraction were grown from acetone solution of (1) over 3 days at room temperature. M.p. 469 K; 91% yield. IR: spectrum, cm-1: 1593 (C=C), 1635 (C=O urea), 1704 (C=O carbamate), 2936–2969 (CH-aliphatic), 3088 (CH-aromatic). 1H-NMR, p.p.m., (DMSO); 0.93 t (3H, CH2—CH3), 1.5 m (2H, CH—CH2—CH3), 3.8 m (1H, CH2—CH—CH2), 4.0 d (2H, O—CH2—CH), 6.1 s (CH—NH—CO), 6.9–7.4 (m, 10H, Ar), 8.4 s (NH—CO—NH—Ph), 9.6 s (O—CO—NH—Ph). 13C-NMR spectrum, d, p.p.m. (DMSO-d): 10.2 (CH3, CH3CH2), 24 (CH2, CH3CH2), 50.2 (CH, CH2—CH—CH2), 66.2 (CH2, O—CH2—CH), 117–128 (10 CH, Ar), 153, 140 (2 C, Ar), 153 (HNCONH, urea), 172 (carbamte).
Carbon-bound H-atoms were placed geometrically (C—H = 0.93 to 0.98 Å) and were refined using a riding model with Uiso=1.2 or 1.5Ueq(C). The N-bound H atom was located from a difference map and refined freely with the distance restraint N—H = 0.86 ± 0.02 Å. In the absence of significant
the could not be reliably determined so the Friedel pairs were merged and any references to the [-0.3 (5)] were removed.Carbamides and
are great classes of organic compounds due to their incorporations in many of bioactive structures. Carbamides, such as N-phenyl-N'-(2-chloroethyl)ureas (CEUs) and benzoylureas (BUs) show good anticancer activity, and these compounds have mainly been proved to be tubulin ligands that inhibit the polymerization of tubulin (Li et al., 2009; Gisbert et al., 2004). such as aldicarb, carbofuran (Furadan), carbaryl (Sevin), ethienocarb, and fenobucarb are widely used as active pesticides (Metcalf, 2002). used also in drug design of anticancer drugs (Ray & Chaturvedi, 2004) and in polymer industry such as polyureathanes. In view of such important applications, we herein report the synthesis and of the title compound (I) having both functions of carbamide and carbamate groups.In (I), (Fig. 1), the orientation of the C1–C6 phenyl ring with respect to the other C13–C18 phenyl ring of the molecule is almost normal by a dihedral angle of 86.3 (5)°. The N1–C7–O2–C8, O2–C8–C9–N2, C9–N2–C12–N3 and C8–C9–C10–C11 torsion angles are 179.8 (5), 169.9 (4), -177.1 (6) and -63.7 (8)°, respectively. The values of the bond lengths and bond angles are consistent with a related structure (Ghalib et al., 2010).
In the crystal, adjacent molecules are interconnected by N—H···O hydrogen bonds (Table 1) into a chain-like structure along the c axis generating parallel C(4) and R21(6) ring motifs (Fig. 2; Bernstein et al., 1995).
For pharmaceutical properties of
and carbamide compounds, see: Li et al. (2009); Gisbert & Pajares (2004); Metcalf (2002); Ray & Chaturvedi (2004). For a related structure, see: Ghalib et al. (2010). For graph-set motifs, see: Bernstein et al. (1995).Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).C18H21N3O3 | F(000) = 696 |
Mr = 327.38 | Dx = 1.198 Mg m−3 |
Monoclinic, Cc | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: C -2yc | Cell parameters from 838 reflections |
a = 10.722 (5) Å | θ = 4.0–72.5° |
b = 22.297 (3) Å | µ = 0.68 mm−1 |
c = 9.109 (3) Å | T = 293 K |
β = 123.570 (6)° | Plate, colourless |
V = 1814.5 (11) Å3 | 0.14 × 0.12 × 0.07 mm |
Z = 4 |
Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer | 1264 reflections with I > 2σ(I) |
Radiation source: Enhance (Cu) X-ray Source | Rint = 0.024 |
Graphite monochromator | θmax = 72.7°, θmin = 4.0° |
Detector resolution: 16.3280 pixels mm-1 | h = −10→13 |
ω scans | k = −26→27 |
2915 measured reflections | l = −11→8 |
1676 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.0822P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
1676 reflections | Δρmax = 0.22 e Å−3 |
231 parameters | Δρmin = −0.22 e Å−3 |
5 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0019 (5) |
C18H21N3O3 | V = 1814.5 (11) Å3 |
Mr = 327.38 | Z = 4 |
Monoclinic, Cc | Cu Kα radiation |
a = 10.722 (5) Å | µ = 0.68 mm−1 |
b = 22.297 (3) Å | T = 293 K |
c = 9.109 (3) Å | 0.14 × 0.12 × 0.07 mm |
β = 123.570 (6)° |
Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer | 1264 reflections with I > 2σ(I) |
2915 measured reflections | Rint = 0.024 |
1676 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 5 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.22 e Å−3 |
1676 reflections | Δρmin = −0.22 e Å−3 |
231 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.2114 (5) | 0.75128 (17) | 0.7981 (6) | 0.1177 (16) | |
O2 | −0.0009 (4) | 0.69881 (13) | 0.6486 (4) | 0.0788 (10) | |
O3 | 0.0605 (5) | 0.51102 (14) | 0.6398 (5) | 0.0941 (16) | |
N1 | 0.0064 (5) | 0.78786 (17) | 0.5510 (5) | 0.0734 (14) | |
N2 | 0.0156 (6) | 0.55146 (15) | 0.8323 (5) | 0.0847 (18) | |
N3 | 0.1249 (6) | 0.45933 (16) | 0.8872 (6) | 0.0886 (18) | |
C1 | 0.0557 (6) | 0.84566 (19) | 0.5415 (6) | 0.0722 (16) | |
C2 | −0.0217 (7) | 0.8733 (2) | 0.3778 (8) | 0.092 (2) | |
C3 | 0.0180 (10) | 0.9309 (3) | 0.3609 (11) | 0.124 (3) | |
C4 | 0.1309 (10) | 0.9615 (3) | 0.5060 (12) | 0.123 (3) | |
C5 | 0.2039 (8) | 0.9341 (3) | 0.6652 (11) | 0.110 (3) | |
C6 | 0.1700 (7) | 0.8764 (2) | 0.6871 (8) | 0.088 (2) | |
C7 | 0.0846 (6) | 0.74643 (18) | 0.6781 (6) | 0.0704 (16) | |
C8 | 0.0670 (7) | 0.6502 (2) | 0.7745 (7) | 0.0822 (18) | |
C9 | −0.0553 (6) | 0.60516 (19) | 0.7281 (6) | 0.0797 (18) | |
C10 | −0.1753 (9) | 0.6283 (3) | 0.7544 (10) | 0.111 (3) | |
C11 | −0.1308 (16) | 0.6430 (4) | 0.9279 (16) | 0.182 (6) | |
C12 | 0.0681 (6) | 0.50769 (18) | 0.7795 (6) | 0.0771 (18) | |
C13 | 0.1897 (7) | 0.4088 (2) | 0.8611 (7) | 0.088 (2) | |
C14 | 0.1571 (11) | 0.3526 (2) | 0.8931 (10) | 0.120 (3) | |
C15 | 0.2259 (17) | 0.3026 (3) | 0.8774 (17) | 0.180 (6) | |
C16 | 0.3162 (16) | 0.3086 (4) | 0.8189 (17) | 0.184 (7) | |
C17 | 0.3521 (12) | 0.3633 (3) | 0.7913 (13) | 0.151 (5) | |
C18 | 0.2891 (9) | 0.4141 (3) | 0.8129 (10) | 0.111 (3) | |
H1N | −0.085 (3) | 0.778 (2) | 0.472 (5) | 0.087 (17)* | |
H2 | −0.09950 | 0.85340 | 0.28010 | 0.1110* | |
H2N | 0.020 (5) | 0.549 (2) | 0.929 (4) | 0.072 (13)* | |
H3 | −0.03200 | 0.94910 | 0.25070 | 0.1480* | |
H3N | 0.092 (6) | 0.456 (2) | 0.954 (6) | 0.087 (15)* | |
H4 | 0.15640 | 1.00020 | 0.49460 | 0.1470* | |
H5 | 0.27940 | 0.95480 | 0.76300 | 0.1320* | |
H6 | 0.22280 | 0.85830 | 0.79760 | 0.1050* | |
H8A | 0.11030 | 0.66520 | 0.89320 | 0.0990* | |
H8B | 0.14570 | 0.63160 | 0.76810 | 0.0990* | |
H9 | −0.10400 | 0.59450 | 0.60360 | 0.0950* | |
H10A | −0.21960 | 0.66380 | 0.68200 | 0.1330* | |
H10B | −0.25340 | 0.59820 | 0.70980 | 0.1330* | |
H11A | −0.20880 | 0.66540 | 0.92430 | 0.2720* | |
H11B | −0.04100 | 0.66660 | 0.98310 | 0.2720* | |
H11C | −0.11230 | 0.60680 | 0.99410 | 0.2720* | |
H14 | 0.08890 | 0.34810 | 0.92510 | 0.1440* | |
H15 | 0.20950 | 0.26490 | 0.90750 | 0.2150* | |
H16 | 0.35410 | 0.27460 | 0.79740 | 0.2200* | |
H17 | 0.41930 | 0.36720 | 0.75760 | 0.1800* | |
H18 | 0.31480 | 0.45190 | 0.79440 | 0.1320* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.073 (3) | 0.078 (2) | 0.119 (3) | −0.0025 (17) | 0.001 (3) | 0.014 (2) |
O2 | 0.086 (2) | 0.0655 (16) | 0.0737 (18) | −0.0028 (14) | 0.0372 (17) | 0.0139 (14) |
O3 | 0.176 (4) | 0.0685 (17) | 0.094 (2) | 0.005 (2) | 0.110 (3) | 0.0044 (16) |
N1 | 0.077 (3) | 0.0649 (19) | 0.074 (2) | −0.0062 (17) | 0.039 (2) | 0.0022 (17) |
N2 | 0.159 (4) | 0.0572 (18) | 0.085 (3) | 0.016 (2) | 0.097 (3) | 0.0076 (18) |
N3 | 0.161 (4) | 0.0644 (19) | 0.095 (3) | 0.021 (2) | 0.105 (3) | 0.0121 (18) |
C1 | 0.089 (3) | 0.060 (2) | 0.085 (3) | −0.001 (2) | 0.059 (3) | 0.006 (2) |
C2 | 0.110 (4) | 0.074 (3) | 0.099 (4) | 0.002 (3) | 0.062 (3) | 0.014 (3) |
C3 | 0.177 (7) | 0.081 (3) | 0.127 (5) | 0.003 (4) | 0.092 (6) | 0.027 (4) |
C4 | 0.161 (7) | 0.070 (3) | 0.159 (7) | −0.015 (4) | 0.102 (6) | 0.009 (4) |
C5 | 0.131 (5) | 0.071 (3) | 0.141 (6) | −0.023 (3) | 0.083 (5) | −0.016 (4) |
C6 | 0.101 (4) | 0.072 (3) | 0.097 (4) | −0.016 (3) | 0.059 (3) | −0.010 (3) |
C7 | 0.081 (3) | 0.052 (2) | 0.076 (3) | 0.0030 (19) | 0.042 (3) | 0.0076 (18) |
C8 | 0.109 (4) | 0.062 (2) | 0.081 (3) | 0.010 (2) | 0.056 (3) | 0.016 (2) |
C9 | 0.124 (4) | 0.057 (2) | 0.081 (3) | 0.007 (2) | 0.071 (3) | 0.0054 (19) |
C10 | 0.150 (6) | 0.079 (3) | 0.145 (6) | 0.008 (4) | 0.108 (5) | 0.010 (3) |
C11 | 0.284 (13) | 0.146 (8) | 0.215 (10) | 0.065 (8) | 0.201 (11) | 0.031 (7) |
C12 | 0.135 (4) | 0.053 (2) | 0.086 (3) | 0.003 (2) | 0.088 (3) | 0.0014 (19) |
C13 | 0.144 (5) | 0.066 (2) | 0.096 (3) | 0.019 (3) | 0.092 (4) | 0.006 (2) |
C14 | 0.218 (8) | 0.068 (3) | 0.147 (5) | 0.020 (4) | 0.146 (6) | 0.015 (3) |
C15 | 0.345 (14) | 0.071 (4) | 0.246 (11) | 0.052 (6) | 0.241 (12) | 0.034 (5) |
C16 | 0.322 (15) | 0.093 (5) | 0.268 (13) | 0.075 (7) | 0.246 (13) | 0.041 (6) |
C17 | 0.228 (10) | 0.113 (5) | 0.204 (9) | 0.051 (6) | 0.178 (9) | 0.020 (5) |
C18 | 0.165 (6) | 0.085 (3) | 0.141 (5) | 0.015 (4) | 0.122 (5) | 0.002 (3) |
O1—C7 | 1.188 (8) | C13—C14 | 1.375 (8) |
O2—C7 | 1.330 (6) | C14—C15 | 1.387 (16) |
O2—C8 | 1.448 (6) | C15—C16 | 1.35 (3) |
O3—C12 | 1.232 (7) | C16—C17 | 1.344 (14) |
N1—C1 | 1.414 (6) | C17—C18 | 1.387 (13) |
N1—C7 | 1.350 (6) | C2—H2 | 0.9300 |
N2—C9 | 1.454 (6) | C3—H3 | 0.9300 |
N2—C12 | 1.342 (7) | C4—H4 | 0.9300 |
N3—C12 | 1.355 (6) | C5—H5 | 0.9300 |
N3—C13 | 1.411 (8) | C6—H6 | 0.9300 |
N1—H1N | 0.86 (4) | C8—H8A | 0.9700 |
N2—H2N | 0.86 (4) | C8—H8B | 0.9700 |
N3—H3N | 0.86 (6) | C9—H9 | 0.9800 |
C1—C6 | 1.390 (8) | C10—H10A | 0.9700 |
C1—C2 | 1.387 (7) | C10—H10B | 0.9700 |
C2—C3 | 1.388 (9) | C11—H11A | 0.9600 |
C3—C4 | 1.381 (12) | C11—H11B | 0.9600 |
C4—C5 | 1.354 (12) | C11—H11C | 0.9600 |
C5—C6 | 1.381 (9) | C14—H14 | 0.9300 |
C8—C9 | 1.515 (9) | C15—H15 | 0.9300 |
C9—C10 | 1.523 (12) | C16—H16 | 0.9300 |
C10—C11 | 1.414 (15) | C17—H17 | 0.9300 |
C13—C18 | 1.364 (13) | C18—H18 | 0.9300 |
C7—O2—C8 | 116.7 (4) | C3—C2—H2 | 120.00 |
C1—N1—C7 | 126.9 (5) | C2—C3—H3 | 120.00 |
C9—N2—C12 | 122.5 (4) | C4—C3—H3 | 120.00 |
C12—N3—C13 | 125.4 (5) | C3—C4—H4 | 121.00 |
C7—N1—H1N | 115 (3) | C5—C4—H4 | 121.00 |
C1—N1—H1N | 118 (3) | C4—C5—H5 | 119.00 |
C9—N2—H2N | 116 (3) | C6—C5—H5 | 119.00 |
C12—N2—H2N | 122 (3) | C1—C6—H6 | 120.00 |
C13—N3—H3N | 119 (3) | C5—C6—H6 | 121.00 |
C12—N3—H3N | 113 (3) | O2—C8—H8A | 110.00 |
N1—C1—C6 | 123.6 (4) | O2—C8—H8B | 110.00 |
C2—C1—C6 | 119.6 (5) | C9—C8—H8A | 110.00 |
N1—C1—C2 | 116.7 (5) | C9—C8—H8B | 110.00 |
C1—C2—C3 | 119.5 (6) | H8A—C8—H8B | 109.00 |
C2—C3—C4 | 120.7 (7) | N2—C9—H9 | 108.00 |
C3—C4—C5 | 118.9 (7) | C8—C9—H9 | 108.00 |
C4—C5—C6 | 122.2 (7) | C10—C9—H9 | 108.00 |
C1—C6—C5 | 119.0 (6) | C9—C10—H10A | 108.00 |
O2—C7—N1 | 110.0 (5) | C9—C10—H10B | 108.00 |
O1—C7—O2 | 124.7 (4) | C11—C10—H10A | 108.00 |
O1—C7—N1 | 125.4 (5) | C11—C10—H10B | 108.00 |
O2—C8—C9 | 107.3 (5) | H10A—C10—H10B | 107.00 |
N2—C9—C10 | 111.0 (5) | C10—C11—H11A | 109.00 |
C8—C9—C10 | 114.1 (5) | C10—C11—H11B | 109.00 |
N2—C9—C8 | 107.7 (5) | C10—C11—H11C | 109.00 |
C9—C10—C11 | 117.5 (10) | H11A—C11—H11B | 110.00 |
N2—C12—N3 | 115.4 (5) | H11A—C11—H11C | 109.00 |
O3—C12—N3 | 122.9 (5) | H11B—C11—H11C | 109.00 |
O3—C12—N2 | 121.7 (4) | C13—C14—H14 | 120.00 |
N3—C13—C14 | 119.0 (8) | C15—C14—H14 | 120.00 |
N3—C13—C18 | 122.0 (5) | C14—C15—H15 | 120.00 |
C14—C13—C18 | 118.9 (7) | C16—C15—H15 | 120.00 |
C13—C14—C15 | 119.9 (12) | C15—C16—H16 | 120.00 |
C14—C15—C16 | 120.1 (9) | C17—C16—H16 | 120.00 |
C15—C16—C17 | 120.5 (12) | C16—C17—H17 | 120.00 |
C16—C17—C18 | 120.1 (13) | C18—C17—H17 | 120.00 |
C13—C18—C17 | 120.2 (8) | C13—C18—H18 | 120.00 |
C1—C2—H2 | 120.00 | C17—C18—H18 | 120.00 |
C7—O2—C8—C9 | 172.8 (5) | C6—C1—C2—C3 | 1.3 (12) |
C8—O2—C7—N1 | −179.8 (5) | C1—C2—C3—C4 | −1.7 (15) |
C8—O2—C7—O1 | 0.8 (9) | C2—C3—C4—C5 | 0.9 (17) |
C1—N1—C7—O1 | −4.2 (10) | C3—C4—C5—C6 | 0.5 (16) |
C7—N1—C1—C6 | −22.7 (10) | C4—C5—C6—C1 | −1.0 (14) |
C1—N1—C7—O2 | 176.3 (5) | O2—C8—C9—C10 | −66.4 (6) |
C7—N1—C1—C2 | 160.8 (6) | O2—C8—C9—N2 | 169.9 (4) |
C12—N2—C9—C8 | −86.4 (6) | C8—C9—C10—C11 | −63.7 (8) |
C9—N2—C12—N3 | −177.1 (6) | N2—C9—C10—C11 | 58.2 (8) |
C12—N2—C9—C10 | 148.1 (6) | N3—C13—C14—C15 | −176.5 (8) |
C9—N2—C12—O3 | 0.9 (10) | C18—C13—C14—C15 | 0.5 (12) |
C13—N3—C12—N2 | −178.2 (6) | N3—C13—C18—C17 | 179.0 (7) |
C13—N3—C12—O3 | 3.9 (10) | C14—C13—C18—C17 | 2.1 (11) |
C12—N3—C13—C18 | 44.7 (10) | C13—C14—C15—C16 | −4.7 (17) |
C12—N3—C13—C14 | −138.4 (7) | C14—C15—C16—C17 | 6 (2) |
N1—C1—C6—C5 | −176.3 (7) | C15—C16—C17—C18 | −3.9 (19) |
C2—C1—C6—C5 | 0.1 (12) | C16—C17—C18—C13 | −0.4 (14) |
N1—C1—C2—C3 | 177.9 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 (4) | 1.97 (4) | 2.831 (7) | 175 (4) |
N2—H2N···O3ii | 0.86 (4) | 2.18 (4) | 2.920 (6) | 145 (4) |
N3—H3N···O3ii | 0.86 (6) | 2.04 (6) | 2.822 (8) | 152 (4) |
C6—H6···O1 | 0.93 | 2.39 | 2.917 (6) | 116 |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H21N3O3 |
Mr | 327.38 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 10.722 (5), 22.297 (3), 9.109 (3) |
β (°) | 123.570 (6) |
V (Å3) | 1814.5 (11) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.14 × 0.12 × 0.07 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Sapphire3, Gemini) |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2915, 1676, 1264 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.619 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.155, 1.05 |
No. of reflections | 1676 |
No. of parameters | 231 |
No. of restraints | 5 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.22, −0.22 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 (4) | 1.97 (4) | 2.831 (7) | 175 (4) |
N2—H2N···O3ii | 0.86 (4) | 2.18 (4) | 2.920 (6) | 145 (4) |
N3—H3N···O3ii | 0.86 (6) | 2.04 (6) | 2.822 (8) | 152 (4) |
Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) x, −y+1, z+1/2. |
Acknowledgements
GAB thanks the Ministry of Education and Science of the Republic of Serbia for financial support (projects 172014 and 172035. The authors also thank Manchester Metropolitan University and Erciyes University for facilitating this study.
References
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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.
Carbamides and carbamates are great classes of organic compounds due to their incorporations in many of bioactive structures. Carbamides, such as N-phenyl-N'-(2-chloroethyl)ureas (CEUs) and benzoylureas (BUs) show good anticancer activity, and these compounds have mainly been proved to be tubulin ligands that inhibit the polymerization of tubulin (Li et al., 2009; Gisbert et al., 2004). Carbamates such as aldicarb, carbofuran (Furadan), carbaryl (Sevin), ethienocarb, and fenobucarb are widely used as active pesticides (Metcalf, 2002). Carbamates used also in drug design of anticancer drugs (Ray & Chaturvedi, 2004) and in polymer industry such as polyureathanes. In view of such important applications, we herein report the synthesis and crystal structure of the title compound (I) having both functions of carbamide and carbamate groups.
In (I), (Fig. 1), the orientation of the C1–C6 phenyl ring with respect to the other C13–C18 phenyl ring of the molecule is almost normal by a dihedral angle of 86.3 (5)°. The N1–C7–O2–C8, O2–C8–C9–N2, C9–N2–C12–N3 and C8–C9–C10–C11 torsion angles are 179.8 (5), 169.9 (4), -177.1 (6) and -63.7 (8)°, respectively. The values of the bond lengths and bond angles are consistent with a related structure (Ghalib et al., 2010).
In the crystal, adjacent molecules are interconnected by N—H···O hydrogen bonds (Table 1) into a chain-like structure along the c axis generating parallel C(4) and R21(6) ring motifs (Fig. 2; Bernstein et al., 1995).