organic compounds
N-[2-(Benzylideneamino)phenyl]-N′-phenylurea
aİlke Education and Health Foundation, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey, bDepartment of Chemistry, Faculty of Science, Erciyes University, 38039 Kayseri, Turkey, cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Erciyes University, 38039 Kayseri, Turkey, dDepartment of Physics, Faculty of Arts and Sciences, Dokuz Eylül University, Buca 35160 İzmir, Turkey, and eDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
*Correspondence e-mail: zeliha.atioglu@kapadokya.edu.tr
In the title compound, C20H17N3O [systematic name: 1-phenyl-3-{2-[(E)- (phenylmethylidene)amino]phenyl}urea], the middle benzene ring forms dihedral angles of 17.65 (17) and 29.48 (14)°, respectively, with the N- and C-bound phenyl rings, while the dihedral angle between the terminal rings is 46.53 (18)°. In the crystal, molecules are linked via N—H⋯O hydrogen bonds, forming helical supramolecular chains running parallel to the c axis via an R12(6) ring motif. The structure was refined as a two-component twin with a 0.966 (3):0.034 (3) domain ratio.
Keywords: crystal structure; twin; non-merohedry; urea.
CCDC reference: 1580619
Structure description
). The classical synthesis reported by Schiff involves the condensation of a carbonyl compound with an amine. Various Schiff base-containing compounds are widely used owing to their antifungal, antibacterial, antimalarial, antiproliferative, anti-inflammatory, antiviral and antipyretic properties. In addition to the aforementioned activities, are used as pigments and dyes, catalysts, intermediates in organic synthesis and as polymer stabilizers (da Silva et al., 2011). In this study, starting from o-phenylenediamine, we synthesized a new hybrid molecule containing imine and urea functionalities in the same molecule.
also known as or are nitrogen analogues of or in which the carbonyl group has been replaced by an imine or azomethine group (Ghose, 1983Referring to Fig. 1, the middle benzene ring (C8–C13) make dihedral angles of 17.65 (17) and 29.48 (14)°, respectively, with the terminal phenyl rings (C1–C6 and C15–C20). The dihedral angle between the latter is 46.53 (18)°. All bond lengths and angles are within normal ranges and are in agreement with those reported for 1-(2-aminophenyl)-3- phenylurea (Mague et al., 2015).
In the crystal, N—H⋯O hydrogen bonds link molecules into chains running parallel to the c axis with an (6) ring motif, Fig. 2 and Table 1.
Synthesis and crystallization
To a solution of [N-(2-aminophenyl)-N′-phenylurea] (0.01 mol, 2.27 g) in absolute ethanol (50 mL) stirred at room temperature was added benzaldehyde (0.01 mol, 1.1 g). The mixture was stirred at reflux conditions, until complete, and then cooled to room temperature. The precipitate was filtered off and washed with cold ethanol. The resulting residue was purified by crystallization from EtOH to afford the title compound (2.1 g, 67% yield) as a light-orange solid (m.p. 473–475 K).
Refinement
Crystal data, data collection and structure . The crystal investigated was refined as a two-component twin by non-merohedry. The twin ratio refined to a value of 0.966 (3):0.034 (3). The N-bound ring displayed high displacement parameters and was refined with several constraints.
details are summarized in Table 2Structural data
CCDC reference: 1580619
https://doi.org/10.1107/S241431461701519X/tk4039sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461701519X/tk4039Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S241431461701519X/tk4039Isup3.cml
Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell
CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C20H17N3O | Dx = 1.265 Mg m−3 |
Mr = 315.36 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 1544 reflections |
a = 10.3381 (6) Å | θ = 4.5–25.2° |
b = 17.6843 (13) Å | µ = 0.08 mm−1 |
c = 9.0562 (5) Å | T = 297 K |
V = 1655.67 (18) Å3 | Prism, light-orange |
Z = 4 | 0.42 × 0.23 × 0.20 mm |
F(000) = 664 |
Rigaku Oxford Diffraction Xcalibur, Eos diffractometer | 2499 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 1574 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: 8.0667 pixels mm-1 | θmax = 26.4°, θmin = 3.0° |
ω scans | h = −12→12 |
Absorption correction: analytical (CrysAlis PRO; Rigaku Oxford Diffraction, 2015) | k = −22→16 |
Tmin = 0.980, Tmax = 0.988 | l = −8→11 |
5335 measured reflections |
Refinement on F2 | 29 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.066 | w = 1/[σ2(Fo2) + (0.0306P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.85 | (Δ/σ)max < 0.001 |
2499 reflections | Δρmax = 0.12 e Å−3 |
217 parameters | Δρmin = −0.12 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. The H atoms attached to C and N atoms were placed in calculated positions (C—H = 0.93 Å and N—H = 0.86 Å) and treated as riding with Uiso(H) = 1.2 or 1.5Ueq(N,C). |
x | y | z | Uiso*/Ueq | ||
O1 | 0.17464 (16) | 0.71846 (10) | 0.29408 (19) | 0.0609 (5) | |
N1 | 0.21897 (19) | 0.66269 (12) | 0.5158 (2) | 0.0554 (6) | |
H1 | 0.2541 | 0.6711 | 0.6004 | 0.066* | |
N2 | 0.28671 (18) | 0.78190 (12) | 0.4728 (2) | 0.0524 (6) | |
H2 | 0.3177 | 0.7775 | 0.5605 | 0.063* | |
N3 | 0.51212 (19) | 0.84938 (10) | 0.5281 (2) | 0.0500 (5) | |
C1 | 0.1652 (3) | 0.59015 (18) | 0.4960 (3) | 0.0578 (7) | |
C2 | 0.2172 (3) | 0.5321 (2) | 0.5740 (4) | 0.0964 (12) | |
H2A | 0.2877 | 0.5412 | 0.6352 | 0.116* | |
C3 | 0.1681 (4) | 0.4604 (2) | 0.5645 (6) | 0.1319 (17) | |
H3 | 0.2041 | 0.4216 | 0.6204 | 0.158* | |
C4 | 0.0664 (5) | 0.4460 (3) | 0.4733 (5) | 0.136 (2) | |
H4 | 0.0337 | 0.3973 | 0.4646 | 0.163* | |
C5 | 0.0134 (5) | 0.5036 (3) | 0.3950 (5) | 0.151 (2) | |
H5 | −0.0563 | 0.4943 | 0.3327 | 0.181* | |
C6 | 0.0625 (4) | 0.5765 (2) | 0.4074 (4) | 0.1091 (13) | |
H6 | 0.0248 | 0.6159 | 0.3546 | 0.131* | |
C7 | 0.2223 (2) | 0.72075 (16) | 0.4189 (3) | 0.0472 (6) | |
C8 | 0.3085 (2) | 0.85135 (15) | 0.4020 (3) | 0.0473 (6) | |
C9 | 0.2214 (3) | 0.88489 (17) | 0.3065 (3) | 0.0578 (7) | |
H9 | 0.1442 | 0.8605 | 0.2837 | 0.069* | |
C10 | 0.2486 (4) | 0.95423 (17) | 0.2450 (3) | 0.0657 (8) | |
H10 | 0.1906 | 0.9759 | 0.1789 | 0.079* | |
C11 | 0.3603 (3) | 0.99154 (17) | 0.2803 (3) | 0.0683 (8) | |
H11 | 0.3770 | 1.0389 | 0.2401 | 0.082* | |
C12 | 0.4482 (3) | 0.95884 (16) | 0.3756 (3) | 0.0575 (7) | |
H12 | 0.5234 | 0.9847 | 0.4007 | 0.069* | |
C13 | 0.4250 (2) | 0.88802 (15) | 0.4337 (3) | 0.0479 (7) | |
C14 | 0.6317 (3) | 0.85566 (15) | 0.5046 (3) | 0.0545 (7) | |
H14 | 0.6585 | 0.8878 | 0.4293 | 0.065* | |
C15 | 0.7306 (3) | 0.81545 (15) | 0.5886 (3) | 0.0539 (7) | |
C16 | 0.8592 (3) | 0.83093 (18) | 0.5624 (3) | 0.0684 (8) | |
H16 | 0.8811 | 0.8696 | 0.4974 | 0.082* | |
C17 | 0.9554 (3) | 0.7904 (2) | 0.6301 (4) | 0.0802 (10) | |
H17 | 1.0418 | 0.8013 | 0.6114 | 0.096* | |
C18 | 0.9223 (4) | 0.7340 (2) | 0.7255 (4) | 0.0858 (11) | |
H18 | 0.9870 | 0.7056 | 0.7705 | 0.103* | |
C19 | 0.7937 (4) | 0.71814 (17) | 0.7563 (4) | 0.0839 (10) | |
H19 | 0.7726 | 0.6802 | 0.8232 | 0.101* | |
C20 | 0.6977 (3) | 0.75878 (17) | 0.6877 (3) | 0.0621 (8) | |
H20 | 0.6112 | 0.7484 | 0.7075 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0729 (12) | 0.0698 (13) | 0.0400 (10) | −0.0055 (10) | −0.0054 (9) | −0.0038 (10) |
N1 | 0.0683 (15) | 0.0557 (13) | 0.0421 (11) | −0.0115 (13) | −0.0086 (11) | 0.0021 (13) |
N2 | 0.0584 (13) | 0.0574 (14) | 0.0413 (12) | −0.0126 (12) | −0.0069 (11) | 0.0018 (12) |
N3 | 0.0507 (12) | 0.0504 (14) | 0.0488 (12) | −0.0037 (12) | −0.0036 (11) | −0.0010 (13) |
C1 | 0.0637 (17) | 0.062 (2) | 0.0476 (16) | −0.0081 (17) | 0.0150 (16) | −0.0039 (17) |
C2 | 0.093 (3) | 0.064 (2) | 0.132 (3) | −0.007 (2) | −0.003 (2) | 0.013 (2) |
C3 | 0.146 (4) | 0.058 (3) | 0.191 (5) | −0.008 (3) | 0.027 (3) | 0.012 (3) |
C4 | 0.193 (5) | 0.089 (3) | 0.124 (4) | −0.064 (4) | 0.073 (4) | −0.043 (3) |
C5 | 0.187 (5) | 0.163 (5) | 0.103 (3) | −0.126 (5) | −0.007 (3) | −0.001 (4) |
C6 | 0.119 (3) | 0.118 (3) | 0.090 (2) | −0.059 (3) | −0.026 (2) | 0.024 (2) |
C7 | 0.0437 (14) | 0.0593 (19) | 0.0386 (15) | 0.0012 (14) | 0.0055 (13) | −0.0026 (15) |
C8 | 0.0549 (17) | 0.0470 (16) | 0.0401 (14) | 0.0026 (14) | 0.0039 (13) | −0.0019 (14) |
C9 | 0.0563 (17) | 0.0654 (19) | 0.0516 (18) | 0.0116 (16) | −0.0051 (14) | −0.0084 (16) |
C10 | 0.081 (2) | 0.064 (2) | 0.0522 (18) | 0.021 (2) | −0.0107 (15) | 0.0018 (18) |
C11 | 0.091 (2) | 0.0533 (18) | 0.0605 (17) | 0.0100 (19) | 0.001 (2) | 0.0124 (17) |
C12 | 0.0656 (19) | 0.0483 (17) | 0.0587 (18) | −0.0056 (15) | 0.0060 (15) | 0.0033 (16) |
C13 | 0.0531 (15) | 0.0501 (17) | 0.0405 (15) | 0.0014 (14) | 0.0028 (13) | 0.0000 (14) |
C14 | 0.0575 (17) | 0.0549 (17) | 0.0512 (15) | −0.0035 (14) | 0.0005 (15) | −0.0004 (15) |
C15 | 0.0533 (17) | 0.0558 (18) | 0.0526 (16) | −0.0012 (15) | −0.0053 (15) | −0.0110 (15) |
C16 | 0.0549 (17) | 0.084 (2) | 0.0657 (18) | 0.0032 (18) | −0.0014 (16) | −0.0070 (18) |
C17 | 0.061 (2) | 0.104 (3) | 0.075 (2) | 0.012 (2) | −0.0023 (19) | −0.023 (2) |
C18 | 0.079 (3) | 0.094 (3) | 0.085 (3) | 0.026 (2) | −0.030 (2) | −0.017 (2) |
C19 | 0.102 (3) | 0.065 (2) | 0.084 (2) | 0.006 (2) | −0.025 (2) | 0.004 (2) |
C20 | 0.0677 (19) | 0.0566 (19) | 0.0622 (17) | −0.0030 (17) | −0.0063 (16) | −0.0011 (16) |
O1—C7 | 1.234 (3) | C9—C10 | 1.376 (3) |
N1—C7 | 1.351 (3) | C9—H9 | 0.9300 |
N1—C1 | 1.409 (3) | C10—C11 | 1.368 (4) |
N1—H1 | 0.8600 | C10—H10 | 0.9300 |
N2—C7 | 1.361 (3) | C11—C12 | 1.381 (3) |
N2—C8 | 1.404 (3) | C11—H11 | 0.9300 |
N2—H2 | 0.8600 | C12—C13 | 1.380 (3) |
N3—C14 | 1.259 (3) | C12—H12 | 0.9300 |
N3—C13 | 1.417 (3) | C14—C15 | 1.460 (4) |
C1—C6 | 1.353 (4) | C14—H14 | 0.9300 |
C1—C2 | 1.357 (4) | C15—C16 | 1.377 (4) |
C2—C3 | 1.368 (5) | C15—C20 | 1.388 (4) |
C2—H2A | 0.9300 | C16—C17 | 1.371 (4) |
C3—C4 | 1.361 (4) | C16—H16 | 0.9300 |
C3—H3 | 0.9300 | C17—C18 | 1.364 (4) |
C4—C5 | 1.356 (6) | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C19 | 1.386 (4) |
C5—C6 | 1.389 (5) | C18—H18 | 0.9300 |
C5—H5 | 0.9300 | C19—C20 | 1.375 (4) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C8—C9 | 1.382 (3) | C20—H20 | 0.9300 |
C8—C13 | 1.398 (3) | ||
C7—N1—C1 | 128.2 (2) | C11—C10—C9 | 120.5 (3) |
C7—N1—H1 | 115.9 | C11—C10—H10 | 119.7 |
C1—N1—H1 | 115.9 | C9—C10—H10 | 119.7 |
C7—N2—C8 | 127.6 (2) | C10—C11—C12 | 120.0 (3) |
C7—N2—H2 | 116.2 | C10—C11—H11 | 120.0 |
C8—N2—H2 | 116.2 | C12—C11—H11 | 120.0 |
C14—N3—C13 | 118.6 (2) | C13—C12—C11 | 120.3 (3) |
C6—C1—C2 | 119.0 (3) | C13—C12—H12 | 119.9 |
C6—C1—N1 | 123.2 (3) | C11—C12—H12 | 119.9 |
C2—C1—N1 | 117.8 (3) | C12—C13—C8 | 119.5 (2) |
C1—C2—C3 | 121.4 (4) | C12—C13—N3 | 123.9 (2) |
C1—C2—H2A | 119.3 | C8—C13—N3 | 116.6 (2) |
C3—C2—H2A | 119.3 | N3—C14—C15 | 123.8 (3) |
C4—C3—C2 | 119.9 (4) | N3—C14—H14 | 118.1 |
C4—C3—H3 | 120.1 | C15—C14—H14 | 118.1 |
C2—C3—H3 | 120.1 | C16—C15—C20 | 119.5 (3) |
C5—C4—C3 | 119.3 (5) | C16—C15—C14 | 119.3 (3) |
C5—C4—H4 | 120.4 | C20—C15—C14 | 121.1 (2) |
C3—C4—H4 | 120.4 | C17—C16—C15 | 121.3 (3) |
C4—C5—C6 | 120.4 (5) | C17—C16—H16 | 119.4 |
C4—C5—H5 | 119.8 | C15—C16—H16 | 119.4 |
C6—C5—H5 | 119.8 | C18—C17—C16 | 118.9 (3) |
C1—C6—C5 | 120.0 (4) | C18—C17—H17 | 120.5 |
C1—C6—H6 | 120.0 | C16—C17—H17 | 120.5 |
C5—C6—H6 | 120.0 | C17—C18—C19 | 121.0 (3) |
O1—C7—N1 | 124.1 (3) | C17—C18—H18 | 119.5 |
O1—C7—N2 | 123.4 (3) | C19—C18—H18 | 119.5 |
N1—C7—N2 | 112.5 (2) | C20—C19—C18 | 119.7 (3) |
C9—C8—C13 | 119.4 (2) | C20—C19—H19 | 120.1 |
C9—C8—N2 | 123.8 (2) | C18—C19—H19 | 120.1 |
C13—C8—N2 | 116.7 (2) | C19—C20—C15 | 119.5 (3) |
C10—C9—C8 | 120.2 (3) | C19—C20—H20 | 120.2 |
C10—C9—H9 | 119.9 | C15—C20—H20 | 120.2 |
C8—C9—H9 | 119.9 | ||
C7—N1—C1—C6 | −30.1 (5) | C10—C11—C12—C13 | 1.0 (4) |
C7—N1—C1—C2 | 152.2 (3) | C11—C12—C13—C8 | −3.5 (3) |
C6—C1—C2—C3 | 0.1 (5) | C11—C12—C13—N3 | 177.8 (2) |
N1—C1—C2—C3 | 177.9 (3) | C9—C8—C13—C12 | 3.5 (3) |
C1—C2—C3—C4 | 1.2 (7) | N2—C8—C13—C12 | −175.6 (2) |
C2—C3—C4—C5 | −1.4 (7) | C9—C8—C13—N3 | −177.7 (2) |
C3—C4—C5—C6 | 0.3 (8) | N2—C8—C13—N3 | 3.2 (3) |
C2—C1—C6—C5 | −1.2 (6) | C14—N3—C13—C12 | −37.0 (3) |
N1—C1—C6—C5 | −178.9 (3) | C14—N3—C13—C8 | 144.3 (2) |
C4—C5—C6—C1 | 1.0 (7) | C13—N3—C14—C15 | −176.5 (2) |
C1—N1—C7—O1 | 1.1 (4) | N3—C14—C15—C16 | −174.6 (3) |
C1—N1—C7—N2 | −177.5 (2) | N3—C14—C15—C20 | 9.3 (4) |
C8—N2—C7—O1 | 1.3 (4) | C20—C15—C16—C17 | 1.3 (4) |
C8—N2—C7—N1 | 179.9 (2) | C14—C15—C16—C17 | −174.8 (3) |
C7—N2—C8—C9 | 34.6 (3) | C15—C16—C17—C18 | −0.2 (4) |
C7—N2—C8—C13 | −146.4 (2) | C16—C17—C18—C19 | −1.2 (5) |
C13—C8—C9—C10 | −0.9 (3) | C17—C18—C19—C20 | 1.4 (5) |
N2—C8—C9—C10 | 178.1 (2) | C18—C19—C20—C15 | −0.3 (4) |
C8—C9—C10—C11 | −1.6 (4) | C16—C15—C20—C19 | −1.1 (4) |
C9—C10—C11—C12 | 1.6 (4) | C14—C15—C20—C19 | 175.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.08 | 2.921 (3) | 166 |
N2—H2···O1i | 0.86 | 2.36 | 3.144 (3) | 152 |
Symmetry code: (i) −x+1/2, y, z+1/2. |
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