Methyl 3-(4-chloro­phen­yl)-2-(1,3-dimethyl-2,5-dioxo-4-phenyl­imidazolidin-4-yl)-3-oxopropano­ate

Abstract

The title compound, C₂₁H₁₉ClN₂O₅, is a tetra­substituted hydantoin derivative which contains an imidazolidine-2,4-dione core. The dihedral angle between the aromatic rings is 64.53 (14)°. In the crystal, weak inter­molecular C—H⋯O hydrogen bonding is found. An intra­molecular C—H⋯O inter­action also occurs.

Related literature

For the preparation of the title compound, see: Gao et al. (2010 ▶).

Experimental

Crystal data

• C₂₁H₁₉ClN₂O₅

• M _r = 414.83

• Monoclinic,

• a = 11.4644 (11) Å

• b = 12.0231 (12) Å

• c = 15.1184 (15) Å

• β = 101.731 (2)°

• V = 2040.4 (3) ų

• Z = 4

• Mo Kα radiation

• μ = 0.22 mm⁻¹

• T = 298 K

• 0.40 × 0.30 × 0.20 mm

Data collection

• Bruker SMART CCD area-detector diffractometer

• 21013 measured reflections

• 4007 independent reflections

• 3573 reflections with I > 2σ(I)

• R _int = 0.059

Refinement

• R[F ² > 2σ(F ²)] = 0.069

• wR(F ²) = 0.164

• S = 1.17

• 4007 reflections

• 265 parameters

• H-atom parameters constrained

• Δρ_max = 0.32 e Å⁻³

• Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811018733/nc2228Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.93	2.49	3.168 (3)	129
C10—H10A⋯O5ii	0.96	2.51	3.235 (4)	132
C15—H15B⋯O2	0.96	2.59	3.312 (4)	132

Symmetry codes: (i) ; (ii) .

supplementary crystallographic information

Experimental

The title compound was synthesized according to the reported literature (Gao et al., 2010). The crystal was grown by slow evaporation of the solvent at room temperature from a chloroform-methanol(1:1) solution of the title compound.

Refinement

All H atoms were positioned in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range of 0.93–0.98 Å and U_iso(H) = 1.2U_eq(C) (1.5 for methyl H atoms).

Figures

Fig. 1.

A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level. H atoms omitted for clarity.

Crystal data

C21H19ClN2O5	F(000) = 864
Mr = 414.83	Dx = 1.350 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6439 reflections
a = 11.4644 (11) Å	θ = 2.2–27.8°
b = 12.0231 (12) Å	µ = 0.22 mm−1
c = 15.1184 (15) Å	T = 298 K
β = 101.731 (2)°	Block, colourless
V = 2040.4 (3) Å3	0.40 × 0.30 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3573 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
graphite	θmax = 26.0°, θmin = 2.0°
φ and ω scans	h = −14→14
21013 measured reflections	k = −14→14
4007 independent reflections	l = −18→18

Refinement

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0623P)2 + 1.2007P] where P = (Fo2 + 2Fc2)/3
4007 reflections	(Δ/σ)max = 0.001
265 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6491 (2)	0.2716 (2)	0.94021 (16)	0.0355 (5)
C2	0.6948 (3)	0.3041 (2)	1.02851 (18)	0.0487 (7)
H2	0.7238	0.2505	1.0718	0.058*
C3	0.6979 (3)	0.4144 (3)	1.05292 (19)	0.0551 (8)
H3	0.7286	0.4356	1.1122	0.066*
C4	0.6548 (2)	0.4928 (2)	0.9885 (2)	0.0482 (7)
C5	0.6083 (3)	0.4641 (2)	0.90104 (19)	0.0493 (7)
H5	0.5786	0.5183	0.8585	0.059*
C6	0.6058 (2)	0.3535 (2)	0.87671 (17)	0.0443 (6)
H6	0.5750	0.3333	0.8172	0.053*
C7	0.6478 (2)	0.1512 (2)	0.91874 (15)	0.0350 (5)
C8	0.6010 (2)	0.1162 (2)	0.81994 (15)	0.0344 (5)
H8	0.6337	0.1691	0.7821	0.041*
C9	0.4663 (2)	0.1244 (2)	0.79297 (18)	0.0437 (6)
C10	0.2854 (3)	0.1228 (4)	0.8447 (3)	0.0785 (11)
H10A	0.2548	0.1872	0.8102	0.118*
H10B	0.2578	0.1223	0.9006	0.118*
H10C	0.2582	0.0569	0.8109	0.118*
C11	0.6383 (2)	−0.0019 (2)	0.79438 (15)	0.0347 (5)
C12	0.6180 (2)	−0.0061 (2)	0.69012 (16)	0.0378 (6)
C13	0.5134 (2)	−0.1486 (2)	0.7368 (2)	0.0483 (7)
C14	0.5159 (3)	−0.1377 (3)	0.5715 (2)	0.0702 (10)
H14A	0.4433	−0.1012	0.5435	0.105*
H14B	0.5033	−0.2166	0.5712	0.105*
H14C	0.5771	−0.1207	0.5386	0.105*
C15	0.5383 (3)	−0.1235 (3)	0.9003 (2)	0.0591 (8)
H15A	0.5019	−0.1958	0.8957	0.089*
H15B	0.4867	−0.0708	0.9207	0.089*
H15C	0.6130	−0.1263	0.9426	0.089*
C16	0.7700 (2)	−0.0284 (2)	0.82963 (15)	0.0352 (5)
C17	0.8069 (3)	−0.1364 (2)	0.85344 (17)	0.0442 (6)
H17	0.7505	−0.1925	0.8509	0.053*
C18	0.9261 (3)	−0.1613 (3)	0.88070 (19)	0.0548 (7)
H18	0.9493	−0.2339	0.8966	0.066*
C19	1.0107 (3)	−0.0798 (3)	0.8845 (2)	0.0615 (8)
H19	1.0910	−0.0964	0.9040	0.074*
C20	0.9752 (3)	0.0270 (3)	0.8592 (2)	0.0607 (8)
H20	1.0322	0.0823	0.8606	0.073*
C21	0.8562 (2)	0.0526 (2)	0.83176 (19)	0.0457 (6)
H21	0.8336	0.1250	0.8146	0.055*
Cl1	0.66072 (9)	0.63209 (7)	1.01981 (7)	0.0773 (3)
N1	0.5525 (2)	−0.0993 (2)	0.66416 (14)	0.0480 (6)
N2	0.55847 (19)	−0.08964 (18)	0.81188 (14)	0.0425 (5)
O1	0.68288 (17)	0.08220 (15)	0.97634 (11)	0.0474 (5)
O2	0.41472 (16)	0.12565 (17)	0.86363 (13)	0.0524 (5)
O3	0.41480 (19)	0.1265 (2)	0.71633 (14)	0.0767 (7)
O4	0.65545 (17)	0.05911 (16)	0.64252 (12)	0.0486 (5)
O5	0.4498 (2)	−0.22967 (19)	0.73042 (17)	0.0748 (7)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0306 (12)	0.0426 (13)	0.0341 (12)	−0.0007 (10)	0.0082 (9)	−0.0021 (10)
C2	0.0519 (16)	0.0500 (16)	0.0380 (14)	0.0056 (13)	−0.0052 (12)	−0.0034 (12)
C3	0.0582 (18)	0.0561 (17)	0.0433 (15)	0.0039 (14)	−0.0077 (13)	−0.0166 (13)
C4	0.0420 (14)	0.0442 (15)	0.0596 (17)	−0.0026 (12)	0.0135 (13)	−0.0134 (13)
C5	0.0577 (17)	0.0422 (15)	0.0504 (16)	0.0018 (13)	0.0165 (13)	0.0041 (12)
C6	0.0520 (15)	0.0484 (15)	0.0325 (13)	−0.0016 (12)	0.0086 (11)	−0.0028 (11)
C7	0.0290 (12)	0.0449 (13)	0.0312 (12)	0.0007 (10)	0.0064 (9)	−0.0012 (10)
C8	0.0341 (12)	0.0382 (13)	0.0310 (12)	−0.0004 (10)	0.0065 (9)	−0.0027 (10)
C9	0.0386 (14)	0.0498 (15)	0.0397 (14)	0.0030 (11)	0.0005 (11)	−0.0070 (12)
C10	0.0333 (16)	0.119 (3)	0.082 (2)	0.0004 (18)	0.0098 (15)	−0.023 (2)
C11	0.0357 (12)	0.0376 (13)	0.0316 (12)	−0.0044 (10)	0.0087 (10)	−0.0019 (10)
C12	0.0358 (13)	0.0432 (14)	0.0343 (13)	0.0058 (11)	0.0066 (10)	−0.0043 (11)
C13	0.0426 (15)	0.0441 (15)	0.0574 (17)	−0.0059 (12)	0.0084 (12)	−0.0077 (13)
C14	0.084 (2)	0.073 (2)	0.0471 (18)	−0.0079 (18)	−0.0021 (16)	−0.0221 (16)
C15	0.072 (2)	0.0542 (17)	0.0597 (19)	−0.0116 (15)	0.0324 (16)	0.0037 (14)
C16	0.0392 (13)	0.0381 (13)	0.0286 (11)	0.0018 (10)	0.0080 (10)	−0.0029 (10)
C17	0.0537 (16)	0.0414 (14)	0.0381 (14)	0.0002 (12)	0.0104 (12)	0.0021 (11)
C18	0.0620 (19)	0.0526 (17)	0.0472 (16)	0.0210 (15)	0.0047 (13)	0.0053 (13)
C19	0.0415 (16)	0.074 (2)	0.0642 (19)	0.0140 (15)	−0.0004 (14)	−0.0005 (16)
C20	0.0378 (15)	0.065 (2)	0.077 (2)	−0.0027 (14)	0.0069 (14)	−0.0041 (16)
C21	0.0388 (14)	0.0416 (14)	0.0568 (16)	0.0012 (11)	0.0102 (12)	0.0016 (12)
Cl1	0.0874 (7)	0.0451 (4)	0.0994 (7)	−0.0030 (4)	0.0187 (5)	−0.0212 (4)
N1	0.0512 (13)	0.0505 (13)	0.0394 (12)	−0.0044 (11)	0.0023 (10)	−0.0118 (10)
N2	0.0428 (12)	0.0443 (12)	0.0424 (12)	−0.0103 (9)	0.0132 (9)	−0.0039 (10)
O1	0.0588 (12)	0.0461 (10)	0.0353 (10)	0.0056 (9)	0.0046 (8)	0.0028 (8)
O2	0.0337 (10)	0.0734 (14)	0.0498 (11)	0.0006 (9)	0.0076 (8)	−0.0116 (10)
O3	0.0454 (12)	0.133 (2)	0.0455 (12)	0.0053 (13)	−0.0058 (9)	−0.0075 (13)
O4	0.0559 (11)	0.0557 (11)	0.0364 (10)	0.0022 (9)	0.0147 (8)	0.0041 (8)
O5	0.0732 (15)	0.0613 (14)	0.0883 (17)	−0.0323 (12)	0.0122 (13)	−0.0147 (12)

Geometric parameters (Å, °)

C1—C2	1.387 (3)	C11—C12	1.547 (3)
C1—C6	1.394 (4)	C12—O4	1.201 (3)
C1—C7	1.483 (3)	C12—N1	1.361 (3)
C2—C3	1.375 (4)	C13—O5	1.209 (3)
C2—H2	0.9300	C13—N2	1.348 (3)
C3—C4	1.373 (4)	C13—N1	1.400 (4)
C3—H3	0.9300	C14—N1	1.453 (3)
C4—C5	1.366 (4)	C14—H14A	0.9600
C4—Cl1	1.738 (3)	C14—H14B	0.9600
C5—C6	1.378 (4)	C14—H14C	0.9600
C5—H5	0.9300	C15—N2	1.460 (3)
C6—H6	0.9300	C15—H15A	0.9600
C7—O1	1.211 (3)	C15—H15B	0.9600
C7—C8	1.540 (3)	C15—H15C	0.9600
C8—C9	1.518 (3)	C16—C21	1.384 (4)
C8—C11	1.554 (3)	C16—C17	1.390 (3)
C8—H8	0.9800	C17—C18	1.377 (4)
C9—O3	1.189 (3)	C17—H17	0.9300
C9—O2	1.322 (3)	C18—C19	1.372 (5)
C10—O2	1.452 (3)	C18—H18	0.9300
C10—H10A	0.9600	C19—C20	1.377 (5)
C10—H10B	0.9600	C19—H19	0.9300
C10—H10C	0.9600	C20—C21	1.378 (4)
C11—N2	1.456 (3)	C20—H20	0.9300
C11—C16	1.529 (3)	C21—H21	0.9300
C2—C1—C6	118.4 (2)	O4—C12—C11	126.2 (2)
C2—C1—C7	118.1 (2)	N1—C12—C11	106.3 (2)
C6—C1—C7	123.5 (2)	O5—C13—N2	127.8 (3)
C3—C2—C1	120.9 (3)	O5—C13—N1	124.2 (3)
C3—C2—H2	119.5	N2—C13—N1	108.0 (2)
C1—C2—H2	119.5	N1—C14—H14A	109.5
C4—C3—C2	119.1 (3)	N1—C14—H14B	109.5
C4—C3—H3	120.5	H14A—C14—H14B	109.5
C2—C3—H3	120.5	N1—C14—H14C	109.5
C5—C4—C3	121.8 (3)	H14A—C14—H14C	109.5
C5—C4—Cl1	119.5 (2)	H14B—C14—H14C	109.5
C3—C4—Cl1	118.7 (2)	N2—C15—H15A	109.5
C4—C5—C6	119.0 (3)	N2—C15—H15B	109.5
C4—C5—H5	120.5	H15A—C15—H15B	109.5
C6—C5—H5	120.5	N2—C15—H15C	109.5
C5—C6—C1	120.8 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.6	H15B—C15—H15C	109.5
C1—C6—H6	119.6	C21—C16—C17	118.3 (2)
O1—C7—C1	121.6 (2)	C21—C16—C11	120.7 (2)
O1—C7—C8	120.6 (2)	C17—C16—C11	120.8 (2)
C1—C7—C8	117.7 (2)	C18—C17—C16	120.8 (3)
C9—C8—C7	112.17 (19)	C18—C17—H17	119.6
C9—C8—C11	107.97 (19)	C16—C17—H17	119.6
C7—C8—C11	115.58 (19)	C19—C18—C17	120.5 (3)
C9—C8—H8	106.9	C19—C18—H18	119.8
C7—C8—H8	106.9	C17—C18—H18	119.8
C11—C8—H8	106.9	C18—C19—C20	119.2 (3)
O3—C9—O2	124.9 (3)	C18—C19—H19	120.4
O3—C9—C8	122.7 (2)	C20—C19—H19	120.4
O2—C9—C8	112.4 (2)	C19—C20—C21	120.7 (3)
O2—C10—H10A	109.5	C19—C20—H20	119.6
O2—C10—H10B	109.5	C21—C20—H20	119.6
H10A—C10—H10B	109.5	C20—C21—C16	120.5 (3)
O2—C10—H10C	109.5	C20—C21—H21	119.7
H10A—C10—H10C	109.5	C16—C21—H21	119.7
H10B—C10—H10C	109.5	C12—N1—C13	111.6 (2)
N2—C11—C16	113.5 (2)	C12—N1—C14	125.0 (3)
N2—C11—C12	101.05 (18)	C13—N1—C14	123.1 (2)
C16—C11—C12	106.35 (18)	C13—N2—C11	112.1 (2)
N2—C11—C8	113.72 (19)	C13—N2—C15	121.2 (2)
C16—C11—C8	113.95 (19)	C11—N2—C15	126.2 (2)
C12—C11—C8	106.94 (19)	C9—O2—C10	116.6 (2)
O4—C12—N1	127.4 (2)
C6—C1—C2—C3	−0.2 (4)	N2—C11—C16—C21	−169.5 (2)
C7—C1—C2—C3	−179.6 (3)	C12—C11—C16—C21	80.4 (3)
C1—C2—C3—C4	0.0 (5)	C8—C11—C16—C21	−37.2 (3)
C2—C3—C4—C5	0.5 (5)	N2—C11—C16—C17	15.7 (3)
C2—C3—C4—Cl1	−179.2 (2)	C12—C11—C16—C17	−94.4 (3)
C3—C4—C5—C6	−0.8 (4)	C8—C11—C16—C17	148.0 (2)
Cl1—C4—C5—C6	179.0 (2)	C21—C16—C17—C18	1.7 (4)
C4—C5—C6—C1	0.6 (4)	C11—C16—C17—C18	176.6 (2)
C2—C1—C6—C5	−0.1 (4)	C16—C17—C18—C19	−0.2 (4)
C7—C1—C6—C5	179.2 (2)	C17—C18—C19—C20	−1.2 (5)
C2—C1—C7—O1	1.6 (4)	C18—C19—C20—C21	1.1 (5)
C6—C1—C7—O1	−177.7 (2)	C19—C20—C21—C16	0.3 (5)
C2—C1—C7—C8	−177.9 (2)	C17—C16—C21—C20	−1.7 (4)
C6—C1—C7—C8	2.8 (3)	C11—C16—C21—C20	−176.6 (3)
O1—C7—C8—C9	105.8 (3)	O4—C12—N1—C13	−173.5 (3)
C1—C7—C8—C9	−74.8 (3)	C11—C12—N1—C13	8.1 (3)
O1—C7—C8—C11	−18.6 (3)	O4—C12—N1—C14	0.5 (4)
C1—C7—C8—C11	160.9 (2)	C11—C12—N1—C14	−178.0 (3)
C7—C8—C9—O3	162.1 (3)	O5—C13—N1—C12	176.9 (3)
C11—C8—C9—O3	−69.4 (3)	N2—C13—N1—C12	−2.7 (3)
C7—C8—C9—O2	−19.6 (3)	O5—C13—N1—C14	2.9 (5)
C11—C8—C9—O2	108.9 (2)	N2—C13—N1—C14	−176.7 (3)
C9—C8—C11—N2	−39.6 (3)	O5—C13—N2—C11	176.0 (3)
C7—C8—C11—N2	86.9 (2)	N1—C13—N2—C11	−4.4 (3)
C9—C8—C11—C16	−171.7 (2)	O5—C13—N2—C15	3.3 (5)
C7—C8—C11—C16	−45.2 (3)	N1—C13—N2—C15	−177.1 (2)
C9—C8—C11—C12	71.1 (2)	C16—C11—N2—C13	−104.7 (2)
C7—C8—C11—C12	−162.42 (19)	C12—C11—N2—C13	8.7 (3)
N2—C11—C12—O4	171.7 (2)	C8—C11—N2—C13	122.9 (2)
C16—C11—C12—O4	−69.6 (3)	C16—C11—N2—C15	67.5 (3)
C8—C11—C12—O4	52.5 (3)	C12—C11—N2—C15	−179.1 (2)
N2—C11—C12—N1	−9.8 (2)	C8—C11—N2—C15	−64.9 (3)
C16—C11—C12—N1	108.9 (2)	O3—C9—O2—C10	3.8 (4)
C8—C11—C12—N1	−129.0 (2)	C8—C9—O2—C10	−174.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.93	2.49	3.168 (3)	129
C10—H10A···O5ii	0.96	2.51	3.235 (4)	132
C15—H15B···O2	0.96	2.59	3.312 (4)	132

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+3/2.