Ethyl 2-(2,5-dioxo-4,4-di­phenyl­imidazolidin-1-yl)acetate

Ramli, Y.; Akrad, R.; Guerrab, W.; Taoufik, J.; Ansar, M.; Mague, J.T.

doi:10.1107/S2414314617000980

Ethyl 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate

Y. Ramli, R. Akrad, W. Guerrab, J. Taoufik, M. Ansar and J. T. Mague

The five-membered ring of the title compound, C₁₉H₁₈N₂O₄, adopts an envelope conformation. In the crystal, pairwise N—H

O hydrogen bonds form centrosymmetric dimers which are connected into chains parallel to the c-axis direction by pairwise C—H

O hydrogen bonds. A second set of C—H

O hydrogen bonds links these chains into sheets oriented parallel to (100). A combination of additional C—H

O hydrogen bonds and C—H

π(ring) interactions combine the sheets into a three-dimensional network.

Keywords: crystal structure; imidazole; hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617000980/sj4081sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314617000980/sj4081Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617000980/sj4081Isup3.cml Supplementary material

CCDC reference: 1528488

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.047
wR factor = 0.130
Data-to-parameter ratio = 106.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A   ..  O4      ..       2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18A   ..  O3      ..       2.66 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.724 Check

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed ..          ! Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         49 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   2 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
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Ethyl 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate top

Crystal data top

C₁₉H₁₈N₂O₄	Z = 2
M_r = 338.35	F(000) = 356
Triclinic, P1	D_x = 1.351 Mg m⁻³
a = 8.5041 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6959 (5) Å	Cell parameters from 9879 reflections
c = 12.5024 (8) Å	θ = 2.6–29.1°
α = 71.002 (1)°	µ = 0.10 mm⁻¹
β = 88.165 (1)°	T = 100 K
γ = 72.572 (1)°	Column, colourless
V = 831.87 (9) Å³	0.43 × 0.29 × 0.26 mm

Data collection top

Bruker SMART APEX CCD diffractometer	31786 independent reflections
Radiation source: fine-focus sealed tube	21954 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.2°, θ_min = 1.7°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −11→11
T_min = 0.96, T_max = 0.97	l = −17→17
31786 measured reflections

Refinement top

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F²) = 0.130	All H-atom parameters refined
S = 1.06	w = 1/[σ²(F_o²) + (0.0527P)² + 0.0554P] where P = (F_o² + 2F_c²)/3
31786 reflections	(Δ/σ)_max < 0.001
299 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 7.5 sec/frame. Analysis of 1461 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the triclinic system and to consist of two major and at least two minor components. Since 91% of the reflections could be indexed on the two major components, it was decided to treat the crystal as having tw components. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

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. The structure was refined as a two-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.66938 (14)	0.42374 (14)	0.40959 (9)	0.0212 (3)
O2	0.48505 (14)	0.30571 (14)	0.11562 (9)	0.0236 (3)
O3	0.85782 (14)	0.08216 (15)	0.34383 (10)	0.0273 (3)
O4	0.73722 (13)	−0.10111 (13)	0.46031 (9)	0.0205 (3)
N1	0.54197 (16)	0.54676 (16)	0.12269 (11)	0.0163 (3)
H1	0.534 (2)	0.603 (2)	0.0466 (17)	0.033 (5)*
N2	0.55850 (16)	0.33561 (16)	0.28322 (10)	0.0168 (3)
C1	0.61488 (18)	0.44787 (19)	0.31540 (12)	0.0160 (3)
C2	0.52414 (18)	0.39103 (19)	0.16561 (13)	0.0165 (3)
C3	0.59387 (18)	0.60646 (19)	0.20887 (12)	0.0143 (3)
C4	0.75973 (18)	0.64172 (19)	0.18369 (12)	0.0157 (3)
C5	0.8844 (2)	0.5282 (2)	0.14690 (14)	0.0207 (3)
H5	0.862 (2)	0.428 (2)	0.1372 (15)	0.025 (5)*
C6	1.0353 (2)	0.5584 (2)	0.12179 (14)	0.0249 (4)
H6	1.121 (2)	0.476 (2)	0.0956 (15)	0.029 (5)*
C7	1.0626 (2)	0.7013 (2)	0.13345 (15)	0.0270 (4)
H7	1.171 (2)	0.725 (2)	0.1153 (16)	0.036 (5)*
C8	0.9406 (2)	0.8130 (2)	0.17129 (15)	0.0272 (4)
H8	0.956 (2)	0.912 (2)	0.1786 (16)	0.035 (5)*
C9	0.7894 (2)	0.7831 (2)	0.19693 (14)	0.0218 (4)
H9	0.702 (2)	0.864 (2)	0.2216 (15)	0.026 (5)*
C10	0.45633 (18)	0.76081 (19)	0.21919 (13)	0.0151 (3)
C11	0.3922 (2)	0.8989 (2)	0.12049 (14)	0.0190 (3)
H11	0.437 (2)	0.894 (2)	0.0486 (15)	0.021 (4)*
C12	0.2686 (2)	1.0425 (2)	0.12466 (15)	0.0219 (4)
H12	0.222 (2)	1.140 (2)	0.0536 (15)	0.027 (5)*
C13	0.2049 (2)	1.0487 (2)	0.22742 (14)	0.0218 (4)
H13	0.117 (2)	1.150 (2)	0.2302 (14)	0.025 (5)*
C14	0.2662 (2)	0.9111 (2)	0.32521 (15)	0.0223 (4)
H14	0.220 (2)	0.911 (2)	0.3975 (16)	0.028 (5)*
C15	0.3926 (2)	0.7678 (2)	0.32182 (14)	0.0191 (3)
H15	0.436 (2)	0.676 (2)	0.3905 (15)	0.024 (5)*
C16	0.5624 (2)	0.1679 (2)	0.35767 (14)	0.0185 (3)
H16A	0.515 (2)	0.177 (2)	0.4279 (16)	0.025 (5)*
H16B	0.497 (2)	0.126 (2)	0.3197 (15)	0.026 (5)*
C17	0.73753 (19)	0.0476 (2)	0.38441 (13)	0.0180 (3)
C18	0.8993 (2)	−0.2297 (2)	0.50004 (16)	0.0238 (4)
H18A	0.964 (2)	−0.185 (2)	0.5386 (15)	0.026 (5)*
H18B	0.955 (2)	−0.249 (2)	0.4347 (16)	0.027 (5)*
C19	0.8664 (2)	−0.3865 (2)	0.57850 (17)	0.0293 (4)
H19A	0.977 (3)	−0.481 (3)	0.6116 (17)	0.039 (6)*
H19B	0.801 (3)	−0.364 (2)	0.6446 (17)	0.039 (6)*
H19C	0.799 (3)	−0.430 (2)	0.5386 (17)	0.039 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0269 (6)	0.0215 (6)	0.0139 (6)	−0.0064 (5)	−0.0011 (4)	−0.0048 (5)
O2	0.0338 (7)	0.0224 (6)	0.0201 (6)	−0.0164 (5)	0.0009 (5)	−0.0072 (5)
O3	0.0228 (6)	0.0235 (7)	0.0349 (7)	−0.0082 (5)	0.0108 (5)	−0.0087 (5)
O4	0.0216 (6)	0.0148 (6)	0.0212 (6)	−0.0043 (4)	0.0010 (4)	−0.0018 (5)
N1	0.0224 (7)	0.0167 (7)	0.0116 (6)	−0.0089 (5)	0.0002 (5)	−0.0042 (5)
N2	0.0217 (7)	0.0142 (7)	0.0142 (6)	−0.0080 (5)	0.0010 (5)	−0.0020 (5)
C1	0.0159 (7)	0.0163 (8)	0.0150 (7)	−0.0040 (6)	0.0029 (5)	−0.0054 (6)
C2	0.0164 (7)	0.0174 (8)	0.0161 (7)	−0.0066 (6)	0.0012 (6)	−0.0048 (6)
C3	0.0177 (7)	0.0153 (8)	0.0112 (7)	−0.0070 (6)	0.0011 (5)	−0.0046 (6)
C4	0.0183 (7)	0.0176 (8)	0.0113 (7)	−0.0073 (6)	0.0006 (5)	−0.0031 (6)
C5	0.0216 (8)	0.0192 (8)	0.0209 (8)	−0.0065 (6)	0.0015 (6)	−0.0060 (7)
C6	0.0190 (8)	0.0295 (10)	0.0241 (9)	−0.0048 (7)	0.0028 (6)	−0.0085 (8)
C7	0.0197 (8)	0.0365 (11)	0.0258 (9)	−0.0144 (8)	0.0017 (7)	−0.0064 (8)
C8	0.0271 (9)	0.0302 (10)	0.0321 (10)	−0.0171 (8)	0.0018 (7)	−0.0130 (8)
C9	0.0218 (8)	0.0254 (9)	0.0237 (9)	−0.0103 (7)	0.0033 (6)	−0.0123 (7)
C10	0.0155 (7)	0.0146 (8)	0.0173 (8)	−0.0077 (6)	0.0012 (5)	−0.0051 (6)
C11	0.0216 (8)	0.0188 (8)	0.0166 (8)	−0.0087 (6)	0.0035 (6)	−0.0036 (7)
C12	0.0219 (8)	0.0173 (8)	0.0238 (9)	−0.0074 (6)	0.0002 (6)	−0.0019 (7)
C13	0.0179 (8)	0.0182 (8)	0.0311 (9)	−0.0058 (6)	0.0027 (7)	−0.0103 (7)
C14	0.0222 (8)	0.0260 (9)	0.0221 (9)	−0.0085 (7)	0.0054 (6)	−0.0119 (7)
C15	0.0217 (8)	0.0203 (8)	0.0154 (8)	−0.0069 (6)	0.0010 (6)	−0.0055 (7)
C16	0.0204 (8)	0.0153 (8)	0.0182 (8)	−0.0077 (6)	0.0027 (6)	−0.0014 (6)
C17	0.0224 (8)	0.0157 (8)	0.0176 (8)	−0.0064 (6)	0.0032 (6)	−0.0073 (6)
C18	0.0218 (8)	0.0188 (9)	0.0272 (9)	−0.0006 (7)	−0.0012 (7)	−0.0077 (7)
C19	0.0322 (10)	0.0221 (9)	0.0264 (10)	−0.0013 (8)	−0.0018 (8)	−0.0047 (8)

Geometric parameters (Å, º) top

O1—C1	1.2088 (17)	C8—H8	0.943 (19)
O2—C2	1.2307 (18)	C9—H9	0.978 (18)
O3—C17	1.2025 (19)	C10—C15	1.389 (2)
O4—C17	1.3325 (19)	C10—C11	1.396 (2)
O4—C18	1.4681 (19)	C11—C12	1.386 (2)
N1—C2	1.3378 (19)	C11—H11	0.975 (18)
N1—C3	1.4687 (18)	C12—C13	1.389 (2)
N1—H1	0.91 (2)	C12—H12	0.996 (18)
N2—C1	1.3760 (19)	C13—C14	1.383 (2)
N2—C2	1.4005 (19)	C13—H13	0.978 (18)
N2—C16	1.4433 (19)	C14—C15	1.392 (2)
C1—C3	1.543 (2)	C14—H14	0.973 (19)
C3—C10	1.533 (2)	C15—H15	0.954 (18)
C3—C4	1.533 (2)	C16—C17	1.515 (2)
C4—C9	1.387 (2)	C16—H16A	0.971 (18)
C4—C5	1.395 (2)	C16—H16B	0.958 (18)
C5—C6	1.392 (2)	C18—C19	1.497 (3)
C5—H5	0.989 (18)	C18—H18A	0.977 (18)
C6—C7	1.383 (2)	C18—H18B	0.968 (19)
C6—H6	0.985 (19)	C19—H19A	1.03 (2)
C7—C8	1.381 (3)	C19—H19B	1.02 (2)
C7—H7	1.01 (2)	C19—H19C	0.99 (2)
C8—C9	1.393 (2)

C17—O4—C18	116.34 (13)	C15—C10—C3	122.84 (13)
C2—N1—C3	113.27 (13)	C11—C10—C3	118.04 (14)
C2—N1—H1	122.0 (12)	C12—C11—C10	120.65 (15)
C3—N1—H1	124.3 (12)	C12—C11—H11	120.4 (10)
C1—N2—C2	111.55 (12)	C10—C11—H11	118.9 (10)
C1—N2—C16	124.09 (13)	C11—C12—C13	120.01 (15)
C2—N2—C16	123.48 (13)	C11—C12—H12	120.1 (10)
O1—C1—N2	125.56 (14)	C13—C12—H12	119.8 (10)
O1—C1—C3	127.87 (14)	C14—C13—C12	119.56 (16)
N2—C1—C3	106.56 (12)	C14—C13—H13	120.5 (10)
O2—C2—N1	128.79 (14)	C12—C13—H13	120.0 (10)
O2—C2—N2	123.61 (14)	C13—C14—C15	120.65 (16)
N1—C2—N2	107.59 (13)	C13—C14—H14	120.7 (11)
N1—C3—C10	109.98 (11)	C15—C14—H14	118.6 (11)
N1—C3—C4	110.84 (12)	C10—C15—C14	120.00 (15)
C10—C3—C4	113.22 (12)	C10—C15—H15	120.4 (11)
N1—C3—C1	100.42 (11)	C14—C15—H15	119.6 (11)
C10—C3—C1	111.28 (12)	N2—C16—C17	111.31 (13)
C4—C3—C1	110.38 (12)	N2—C16—H16A	109.3 (11)
C9—C4—C5	119.09 (14)	C17—C16—H16A	109.1 (10)
C9—C4—C3	121.76 (14)	N2—C16—H16B	107.2 (11)
C5—C4—C3	119.15 (13)	C17—C16—H16B	110.0 (11)
C6—C5—C4	120.39 (16)	H16A—C16—H16B	109.8 (15)
C6—C5—H5	121.0 (11)	O3—C17—O4	125.56 (15)
C4—C5—H5	118.6 (11)	O3—C17—C16	125.00 (15)
C7—C6—C5	120.01 (17)	O4—C17—C16	109.44 (13)
C7—C6—H6	121.3 (11)	O4—C18—C19	106.36 (15)
C5—C6—H6	118.7 (11)	O4—C18—H18A	108.3 (11)
C8—C7—C6	119.93 (16)	C19—C18—H18A	112.0 (11)
C8—C7—H7	119.3 (11)	O4—C18—H18B	108.4 (11)
C6—C7—H7	120.8 (11)	C19—C18—H18B	112.7 (10)
C7—C8—C9	120.29 (17)	H18A—C18—H18B	108.9 (15)
C7—C8—H8	121.1 (12)	C18—C19—H19A	109.9 (11)
C9—C8—H8	118.6 (12)	C18—C19—H19B	112.2 (11)
C4—C9—C8	120.27 (16)	H19A—C19—H19B	108.1 (16)
C4—C9—H9	119.2 (10)	C18—C19—H19C	111.1 (12)
C8—C9—H9	120.5 (10)	H19A—C19—H19C	109.3 (16)
C15—C10—C11	119.11 (14)	H19B—C19—H19C	106.1 (17)

C2—N2—C1—O1	−172.06 (14)	C4—C5—C6—C7	0.1 (2)
C16—N2—C1—O1	−2.5 (2)	C5—C6—C7—C8	0.8 (3)
C2—N2—C1—C3	8.07 (16)	C6—C7—C8—C9	−0.5 (3)
C16—N2—C1—C3	177.66 (13)	C5—C4—C9—C8	1.4 (2)
C3—N1—C2—O2	−178.70 (15)	C3—C4—C9—C8	−178.82 (14)
C3—N1—C2—N2	1.34 (17)	C7—C8—C9—C4	−0.6 (3)
C1—N2—C2—O2	173.90 (14)	N1—C3—C10—C15	126.47 (15)
C16—N2—C2—O2	4.2 (2)	C4—C3—C10—C15	−108.93 (16)
C1—N2—C2—N1	−6.13 (17)	C1—C3—C10—C15	16.09 (19)
C16—N2—C2—N1	−175.80 (13)	N1—C3—C10—C11	−52.87 (17)
C2—N1—C3—C10	−114.14 (14)	C4—C3—C10—C11	71.73 (17)
C2—N1—C3—C4	119.90 (14)	C1—C3—C10—C11	−163.25 (13)
C2—N1—C3—C1	3.23 (16)	C15—C10—C11—C12	1.1 (2)
O1—C1—C3—N1	173.53 (15)	C3—C10—C11—C12	−179.49 (13)
N2—C1—C3—N1	−6.61 (14)	C10—C11—C12—C13	−1.3 (2)
O1—C1—C3—C10	−70.07 (19)	C11—C12—C13—C14	0.3 (2)
N2—C1—C3—C10	109.79 (13)	C12—C13—C14—C15	0.9 (2)
O1—C1—C3—C4	56.5 (2)	C11—C10—C15—C14	0.1 (2)
N2—C1—C3—C4	−123.62 (13)	C3—C10—C15—C14	−179.25 (14)
N1—C3—C4—C9	138.84 (14)	C13—C14—C15—C10	−1.1 (2)
C10—C3—C4—C9	14.70 (19)	C1—N2—C16—C17	−70.75 (19)
C1—C3—C4—C9	−110.80 (16)	C2—N2—C16—C17	97.63 (17)
N1—C3—C4—C5	−41.42 (18)	C18—O4—C17—O3	2.5 (2)
C10—C3—C4—C5	−165.55 (13)	C18—O4—C17—C16	−176.91 (13)
C1—C3—C4—C5	68.94 (17)	N2—C16—C17—O3	−4.4 (2)
C9—C4—C5—C6	−1.2 (2)	N2—C16—C17—O4	174.99 (12)
C3—C4—C5—C6	179.04 (14)	C17—O4—C18—C19	−176.90 (14)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C4–C9 and C10–C15 benzene rings, respectively,

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.91 (2)	1.91 (2)	2.8203 (17)	172.6 (17)
C15—H15···O1ⁱⁱ	0.954 (18)	2.591 (18)	3.332 (2)	134.8 (14)
C16—H16A···O4ⁱⁱⁱ	0.971 (18)	2.653 (19)	3.415 (2)	135.7 (13)
C18—H18A···O3^iv	0.977 (18)	2.658 (19)	3.633 (2)	175.9 (14)
C7—H7···Cg3^v	1.01 (2)	2.976 (18)	3.6661 (19)	126.6 (13)
C12—H12···Cg2^vi	0.996 (18)	2.701 (18)	3.6673 (19)	163.1 (18)
C19—H19A···Cg2	1.03 (2)	2.83 (2)	3.572 (2)	129.0 (16)

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+1; (v) x+1, y, z; (vi) −x+1, −y+2, −z.

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Ethyl 2-(2,5-dioxo-4,4-di­phenyl­imidazolidin-1-yl)acetate

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Ethyl 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate