organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

3-Ethyl-5,5-di­phenyl­imidazolidine-2,4-dione

CROSSMARK_Color_square_no_text.svg

aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: gerrab_walid@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 29 October 2017; accepted 1 November 2017; online 7 November 2017)

In the title mol­ecule, C17H16N2O2, the phenyl rings attached at the 5-position of the imidazolidine-2,4-dione ring are inclined to the five-membered ring by 60.03 (5) and 63.04 (5)°. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds form chains along the a-axis direction, which are connected in pairs by additional C—H⋯O hydrogen bonds. The chains are tied together by C—H⋯π(ring) inter­actions.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

As part of our ongoing studies of 5,5-di­phenyl­imidazolidine-2,4-dione derivatives (Ramli et al., 2017a[Ramli, Y., Akrad, R., Guerrab, W., Taoufik, J., Ansar, M. & Mague, J. T. (2017a). IUCrData, 2, x170098.],b[Ramli, Y., Guerrab, W., Moussaif, A., Taoufik, J., Essassi, E. M. & Mague, J. T. (2017b). IUCrData, 2, x171041.]; Akrad et al. 2017[Akrad, R., Mague, J. T., Guerrab, W., Taoufik, J., Ansar, M. & Ramli, Y. (2017). IUCrData, 2, x170033.]; Guerrab et al. 2017[Guerrab, W., Akrad, R., Ansar, M., Taoufik, J., Mague, J. T. & Ramli, Y. (2017). IUCrData, 2, x171534.]), the title compound was prepared and its crystal structure is reported here.

In the title mol­ecule, Fig. 1[link], the imidazolidine-2,4-dione ring has two phenyl rings attached at the 5-position. These are inclined to the five-membered ring by 60.03 (5) (C6–C11) and 63.04 (5)° (C12–C17).

[Figure 1]
Figure 1
The title mol­ecule showing the labeling scheme and 50% probability displacement ellipsoids for the non-hydrogen atoms.

In the crystal, N2—H2⋯O1i and C4—H4A⋯O2ii hydrogen bonds link the mol­ecules, forming chains along the a-axis direction. Two adjacent chains are joined into ribbons (i.e. one-dimensional assemblies) parallel to [100] by inversion-related C4—H4B⋯O2ii hydrogen bonds that enclose R22(8) rings (Table 1[link] and Fig. 2[link]). The ribbons are further associated through C15—H15⋯Cg2iv inter­actions (Table 1[link] and Fig. 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C6–C11 phenyl ring.

D—H⋯A D—H H⋯A DA D—H⋯A
N2—H2⋯O1i 0.885 (15) 1.947 (15) 2.8270 (11) 172.4 (13)
C4—H4A⋯O2ii 0.980 (14) 2.533 (13) 3.3215 (13) 137.5 (10)
C4—H4B⋯O2iii 0.977 (14) 2.552 (13) 3.3013 (12) 133.4 (10)
C15—H15⋯Cg2iv 0.964 (18) 2.84 (2) 3.646 (1) 141.7 (14)
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z; (iii) -x+1, -y+2, -z+1; (iv) [x-{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{3\over 2}}].
[Figure 2]
Figure 2
Detail of the chains formed along a by N—H⋯O and C—H⋯O hydrogen bonds (blue and black dashed lines, respectively) and linked into ribbons parallel to (0[\overline{1}]1).
[Figure 3]
Figure 3
Packing viewed along the a-axis direction showing the association of chains through C—H⋯π(ring) inter­actions (green dashed lines).

Synthesis and crystallization

To a solution of 5,5-di­phenyl­imidazolidine-2,4-dion (1 g, 3.96 mmol), one equivalent of ethyl bromide (0.43 g) in absolute DMF was added and heated under reflux for 3 h in the presence of 1.3 equivalents of K2CO3. The reaction mixture was filtered while hot, and the solvent evaporated under reduced pressure. The residue obtained was dried and crystallized from ethanol solution to yield colourless block-shaped crystals of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C17H16N2O2
Mr 280.32
Crystal system, space group Monoclinic, P21/n
Temperature (K) 150
a, b, c (Å) 6.2175 (2), 15.5036 (5), 15.3736 (5)
β (°) 98.012 (1)
V3) 1467.45 (8)
Z 4
Radiation type Cu Kα
μ (mm−1) 0.68
Crystal size (mm) 0.27 × 0.23 × 0.14
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.84, 0.91
No. of measured, independent and observed [I > 2σ(I)] reflections 22530, 2977, 2804
Rint 0.036
(sin θ/λ)max−1) 0.625
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.081, 1.04
No. of reflections 2977
No. of parameters 255
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.24, −0.18
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2016 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND, Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Ethyl-5,5-diphenylimidazolidine-2,4-dione top
Crystal data top
C17H16N2O2F(000) = 592
Mr = 280.32Dx = 1.269 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 6.2175 (2) ÅCell parameters from 9415 reflections
b = 15.5036 (5) Åθ = 2.9–74.5°
c = 15.3736 (5) ŵ = 0.68 mm1
β = 98.012 (1)°T = 150 K
V = 1467.45 (8) Å3Block, colourles
Z = 40.27 × 0.23 × 0.14 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
2977 independent reflections
Radiation source: INCOATEC IµS micro-focus source2804 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.036
Detector resolution: 10.4167 pixels mm-1θmax = 74.4°, θmin = 4.1°
ω scansh = 76
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1919
Tmin = 0.84, Tmax = 0.91l = 1918
22530 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033All H-atom parameters refined
wR(F2) = 0.081 w = 1/[σ2(Fo2) + (0.0329P)2 + 0.5063P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2977 reflectionsΔρmax = 0.24 e Å3
255 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL2016 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0110 (5)
Special details top

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. 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 > 2sigma(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 (Å2) top
xyzUiso*/Ueq
O10.02846 (11)0.80012 (5)0.28794 (5)0.02339 (18)
O20.64834 (12)0.92452 (5)0.42726 (5)0.0308 (2)
N10.30545 (13)0.87404 (5)0.37070 (5)0.01958 (19)
N20.59292 (13)0.82270 (5)0.31698 (5)0.02024 (19)
H20.732 (2)0.8135 (9)0.3127 (9)0.032 (3)*
C10.40946 (14)0.77880 (6)0.26630 (6)0.0176 (2)
C20.22036 (15)0.81752 (6)0.30855 (6)0.0175 (2)
C30.53431 (16)0.87836 (6)0.37683 (6)0.0203 (2)
C40.18308 (17)0.92347 (7)0.42886 (7)0.0228 (2)
H4A0.038 (2)0.9333 (8)0.3968 (8)0.026 (3)*
H4B0.256 (2)0.9791 (9)0.4383 (8)0.028 (3)*
C50.1716 (2)0.87682 (9)0.51397 (8)0.0364 (3)
H5A0.103 (3)0.8208 (11)0.5029 (11)0.049 (4)*
H5B0.086 (3)0.9098 (10)0.5514 (11)0.045 (4)*
H5C0.320 (3)0.8698 (11)0.5478 (11)0.049 (4)*
C60.42774 (15)0.68098 (6)0.27939 (6)0.0194 (2)
C70.59603 (18)0.63822 (7)0.24610 (7)0.0266 (2)
H70.697 (2)0.6714 (9)0.2124 (9)0.035 (4)*
C80.6263 (2)0.55032 (8)0.25929 (8)0.0327 (3)
H80.745 (3)0.5221 (10)0.2354 (10)0.046 (4)*
C90.4889 (2)0.50432 (7)0.30558 (8)0.0350 (3)
H90.510 (3)0.4428 (11)0.3164 (11)0.050 (4)*
C100.3218 (2)0.54604 (8)0.33872 (9)0.0384 (3)
H100.223 (3)0.5123 (11)0.3700 (11)0.054 (5)*
C110.29031 (19)0.63426 (7)0.32556 (8)0.0301 (3)
H110.168 (2)0.6641 (9)0.3503 (10)0.038 (4)*
C120.38141 (16)0.80267 (6)0.16860 (6)0.0199 (2)
C130.53462 (18)0.85206 (7)0.13385 (7)0.0278 (2)
H130.665 (2)0.8718 (9)0.1728 (9)0.033 (3)*
C140.5034 (2)0.87438 (8)0.04508 (8)0.0369 (3)
H140.618 (3)0.9090 (11)0.0219 (11)0.052 (4)*
C150.3187 (2)0.84836 (9)0.00873 (8)0.0389 (3)
H150.295 (3)0.8651 (11)0.0697 (12)0.054 (5)*
C160.1665 (2)0.79836 (9)0.02544 (8)0.0378 (3)
H160.034 (3)0.7799 (11)0.0117 (12)0.055 (5)*
C170.19777 (18)0.77468 (8)0.11325 (7)0.0291 (3)
H170.090 (2)0.7373 (10)0.1373 (10)0.042 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0137 (3)0.0289 (4)0.0277 (4)0.0010 (3)0.0033 (3)0.0060 (3)
O20.0207 (4)0.0365 (4)0.0346 (4)0.0050 (3)0.0023 (3)0.0174 (3)
N10.0153 (4)0.0230 (4)0.0210 (4)0.0001 (3)0.0044 (3)0.0057 (3)
N20.0123 (4)0.0266 (4)0.0220 (4)0.0013 (3)0.0033 (3)0.0072 (3)
C10.0130 (4)0.0215 (5)0.0183 (5)0.0011 (3)0.0026 (3)0.0036 (3)
C20.0152 (5)0.0194 (4)0.0182 (4)0.0003 (3)0.0034 (3)0.0004 (3)
C30.0166 (5)0.0231 (5)0.0213 (5)0.0010 (4)0.0028 (4)0.0028 (4)
C40.0194 (5)0.0248 (5)0.0251 (5)0.0023 (4)0.0059 (4)0.0079 (4)
C50.0433 (7)0.0395 (7)0.0295 (6)0.0091 (6)0.0163 (5)0.0010 (5)
C60.0188 (5)0.0216 (5)0.0170 (4)0.0007 (4)0.0002 (3)0.0029 (3)
C70.0279 (6)0.0277 (5)0.0250 (5)0.0050 (4)0.0070 (4)0.0021 (4)
C80.0356 (6)0.0286 (6)0.0336 (6)0.0098 (5)0.0042 (5)0.0063 (5)
C90.0400 (7)0.0207 (5)0.0424 (7)0.0020 (5)0.0010 (5)0.0022 (5)
C100.0387 (7)0.0266 (6)0.0517 (8)0.0040 (5)0.0121 (6)0.0053 (5)
C110.0270 (6)0.0263 (5)0.0390 (6)0.0000 (4)0.0113 (5)0.0010 (5)
C120.0209 (5)0.0202 (5)0.0189 (5)0.0033 (4)0.0042 (4)0.0022 (4)
C130.0298 (6)0.0287 (5)0.0259 (5)0.0031 (4)0.0077 (4)0.0003 (4)
C140.0488 (7)0.0348 (6)0.0299 (6)0.0019 (5)0.0152 (5)0.0053 (5)
C150.0549 (8)0.0416 (7)0.0200 (5)0.0102 (6)0.0053 (5)0.0049 (5)
C160.0388 (7)0.0494 (7)0.0229 (6)0.0036 (6)0.0038 (5)0.0030 (5)
C170.0270 (6)0.0371 (6)0.0226 (5)0.0023 (4)0.0011 (4)0.0034 (4)
Geometric parameters (Å, º) top
O1—C21.2212 (12)C7—H71.007 (14)
O2—C31.2094 (12)C8—C91.3836 (18)
N1—C21.3489 (12)C8—H80.972 (16)
N1—C31.4145 (12)C9—C101.3801 (18)
N1—C41.4682 (12)C9—H90.974 (17)
N2—C31.3481 (13)C10—C111.3924 (17)
N2—C11.4572 (12)C10—H100.980 (18)
N2—H20.885 (15)C11—H111.010 (15)
C1—C61.5321 (13)C12—C131.3859 (14)
C1—C121.5332 (13)C12—C171.3946 (15)
C1—C21.5419 (12)C13—C141.3949 (16)
C4—C51.5054 (16)C13—H130.988 (14)
C4—H4A0.980 (14)C14—C151.379 (2)
C4—H4B0.977 (14)C14—H140.996 (17)
C5—H5A0.972 (17)C15—C161.382 (2)
C5—H5B0.979 (16)C15—H150.964 (18)
C5—H5C1.002 (17)C16—C171.3863 (16)
C6—C111.3884 (15)C16—H160.979 (18)
C6—C71.3948 (14)C17—H170.996 (16)
C7—C81.3868 (16)
C2—N1—C3111.69 (8)C8—C7—C6120.45 (10)
C2—N1—C4125.81 (8)C8—C7—H7119.7 (8)
C3—N1—C4122.45 (8)C6—C7—H7119.8 (8)
C3—N2—C1113.45 (8)C9—C8—C7120.05 (11)
C3—N2—H2120.9 (9)C9—C8—H8121.2 (9)
C1—N2—H2125.6 (9)C7—C8—H8118.7 (9)
N2—C1—C6110.73 (8)C10—C9—C8119.93 (11)
N2—C1—C12112.63 (8)C10—C9—H9119.0 (10)
C6—C1—C12111.34 (8)C8—C9—H9121.1 (10)
N2—C1—C2100.31 (7)C9—C10—C11120.30 (11)
C6—C1—C2112.15 (8)C9—C10—H10119.0 (10)
C12—C1—C2109.23 (8)C11—C10—H10120.7 (10)
O1—C2—N1126.86 (9)C6—C11—C10120.17 (11)
O1—C2—C1125.42 (8)C6—C11—H11120.3 (8)
N1—C2—C1107.72 (8)C10—C11—H11119.5 (8)
O2—C3—N2128.77 (9)C13—C12—C17119.01 (10)
O2—C3—N1124.41 (9)C13—C12—C1121.37 (9)
N2—C3—N1106.81 (8)C17—C12—C1119.62 (9)
N1—C4—C5111.71 (9)C12—C13—C14120.31 (11)
N1—C4—H4A107.2 (8)C12—C13—H13119.2 (8)
C5—C4—H4A111.1 (8)C14—C13—H13120.4 (8)
N1—C4—H4B106.3 (8)C15—C14—C13120.35 (11)
C5—C4—H4B111.9 (8)C15—C14—H14121.3 (10)
H4A—C4—H4B108.4 (11)C13—C14—H14118.3 (10)
C4—C5—H5A110.4 (10)C14—C15—C16119.53 (11)
C4—C5—H5B110.8 (9)C14—C15—H15120.3 (10)
H5A—C5—H5B108.1 (13)C16—C15—H15120.1 (10)
C4—C5—H5C110.6 (9)C15—C16—C17120.55 (12)
H5A—C5—H5C110.1 (13)C15—C16—H16120.5 (10)
H5B—C5—H5C106.7 (13)C17—C16—H16118.9 (10)
C11—C6—C7119.10 (10)C16—C17—C12120.22 (11)
C11—C6—C1122.95 (9)C16—C17—H17120.3 (9)
C7—C6—C1117.90 (9)C12—C17—H17119.5 (9)
C3—N2—C1—C6119.72 (9)C12—C1—C6—C758.81 (11)
C3—N2—C1—C12114.89 (9)C2—C1—C6—C7178.45 (8)
C3—N2—C1—C21.12 (10)C11—C6—C7—C80.30 (16)
C3—N1—C2—O1179.73 (9)C1—C6—C7—C8177.20 (10)
C4—N1—C2—O12.79 (16)C6—C7—C8—C90.14 (17)
C3—N1—C2—C10.49 (11)C7—C8—C9—C100.09 (18)
C4—N1—C2—C1177.97 (9)C8—C9—C10—C110.2 (2)
N2—C1—C2—O1179.81 (9)C7—C6—C11—C100.42 (17)
C6—C1—C2—O162.27 (12)C1—C6—C11—C10176.94 (11)
C12—C1—C2—O161.65 (12)C9—C10—C11—C60.4 (2)
N2—C1—C2—N10.93 (10)N2—C1—C12—C137.69 (13)
C6—C1—C2—N1118.48 (8)C6—C1—C12—C13117.37 (10)
C12—C1—C2—N1117.60 (9)C2—C1—C12—C13118.23 (10)
C1—N2—C3—O2178.95 (10)N2—C1—C12—C17171.99 (9)
C1—N2—C3—N10.90 (11)C6—C1—C12—C1762.94 (12)
C2—N1—C3—O2179.64 (10)C2—C1—C12—C1761.46 (11)
C4—N1—C3—O22.78 (16)C17—C12—C13—C140.96 (16)
C2—N1—C3—N20.22 (11)C1—C12—C13—C14178.72 (10)
C4—N1—C3—N2177.36 (9)C12—C13—C14—C150.72 (18)
C2—N1—C4—C591.96 (13)C13—C14—C15—C161.38 (19)
C3—N1—C4—C585.27 (12)C14—C15—C16—C170.3 (2)
N2—C1—C6—C11110.08 (11)C15—C16—C17—C121.35 (19)
C12—C1—C6—C11123.80 (10)C13—C12—C17—C161.99 (16)
C2—C1—C6—C111.06 (13)C1—C12—C17—C16177.70 (10)
N2—C1—C6—C767.31 (11)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C6–C11 phenyl ring.
D—H···AD—HH···AD···AD—H···A
N2—H2···O1i0.885 (15)1.947 (15)2.8270 (11)172.4 (13)
C4—H4A···O2ii0.980 (14)2.533 (13)3.3215 (13)137.5 (10)
C4—H4B···O2iii0.977 (14)2.552 (13)3.3013 (12)133.4 (10)
C15—H15···Cg2iv0.964 (18)2.84 (2)3.646 (1)141.7 (14)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x+1, y+2, z+1; (iv) x3/2, y+1/2, z3/2.
 

Acknowledgements

The support of NSF-MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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