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

Zhang, D.; Deng, C.; Yang, Y.

doi:10.1107/S1600536811018733

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1508

doi:10.1107/S1600536811018733

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

Dongxue Zhang,^a Cong Deng ^a and Yan Yang ^a ^*

^aKey Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
^*Correspondence e-mail: hbdongxue@163.com

(Received 13 April 2011; accepted 17 May 2011; online 25 May 2011)

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, P 2₁ /n
a = 11.4644 (11) Å
b = 12.0231 (12) Å
c = 15.1184 (15) Å
β = 101.731 (2)°
V = 2040.4 (3) Å³
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[F² > 2σ(F²)] = 0.069
wR(F²) = 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

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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811018733/nc2228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018733/nc2228Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811018733/nc2228Isup3.cml

checkCIF report

Related literature top

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

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top

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.

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

Crystal data top

C₂₁H₁₉ClN₂O₅	F(000) = 864
M_r = 414.83	D_x = 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 top

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

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0623P)² + 1.2007P] where P = (F_o² + 2F_c²)/3
4007 reflections	(Δ/σ)_max = 0.001
265 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₉ClN₂O₅	V = 2040.4 (3) Å³
M_r = 414.83	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.4644 (11) Å	µ = 0.22 mm⁻¹
b = 12.0231 (12) Å	T = 298 K
c = 15.1184 (15) Å	0.40 × 0.30 × 0.20 mm
β = 101.731 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3573 reflections with I > 2σ(I)
21013 measured reflections	R_int = 0.059
4007 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.17	Δρ_max = 0.32 e Å⁻³
4007 reflections	Δρ_min = −0.22 e Å⁻³
265 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉ClN₂O₅
M_r	414.83
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.4644 (11), 12.0231 (12), 15.1184 (15)
β (°)	101.731 (2)
V (Å³)	2040.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21013, 4007, 3573
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.164, 1.17
No. of reflections	4007
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.22

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

The authors are grateful to the Central China Normal University for financial support and thank Dr Xiang-Gao Meng for the X-ray data collection.

References

Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gao, M., Yang, Y., Wu, Y.-D., Deng, C., Shu, W.-M., Zhang, D.-X., Cao, L.-P., She, N.-F. & Wu, A.-X. (2010). Org. Lett. 12, 4026–4029. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 6| June 2011| Page o1508

doi:10.1107/S1600536811018733

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

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

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