Ethyl 2-[(Z)-4-isobutyl-5-oxo-2-(phenyl­imino)imidazolidin-1-yl]acetate

Sun, Y.; Li, H.-X.; He, P.; Li, G.

doi:10.1107/S1600536807058473

Ethyl 2-[(Z)-4-isobutyl-5-oxo-2-(phenylimino)imidazolidin-1-yl]acetate

Y. Sun, H.-X. Li, P. He and G. Li

In the crystal structure of the title compound, C₁₇H₂₃N₃O₃, intermolecular N—H

O and C—H

O hydrogen bonds are present. The planar heterocyclic ring makes a dihedral angle of 64.4 (1)° with the phenyl ring.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058473/at2473sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058473/at2473Isup2.hkl Contains datablock I

CCDC reference: 672985

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
R factor = 0.069
wR factor = 0.195
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.94 Ratio

Author Response: This is owing to disorder, e.g. in i-butyl moieties.

PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.25 Ratio

Author Response: This is owing to disorder, e.g. in i-butyl moieties.

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C11

Author Response: This is owing to disorder, e.g. in i-butyl moieties.


Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.101
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15

Author Response: This is owing to disorder, e.g. in i-butyl moieties.

PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

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

Related literature top

Related preparation and biological activity is described by Lacroix et al. (2000a,b). For related literature, see: Li & Hu (2006).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme.
	Fig. 2. The packing in the crystal structure, showing the N—H···O and C—H···O hydrogen bonds as dashed lines.
	Fig. 3. Preparation of the title compound.

Ethyl 2-[(Z)-4-isobutyl-5-oxo-2-(phenylimino)imidazolidin-1-yl]acetate top

Crystal data top

C₁₇H₂₃N₃O₃	F(000) = 1360
M_r = 317.38	D_x = 1.194 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3517 reflections
a = 16.059 (2) Å	θ = 2.3–21.8°
b = 10.6310 (16) Å	µ = 0.08 mm⁻¹
c = 20.690 (3) Å	T = 292 K
V = 3532.2 (9) Å³	Block, colorless
Z = 8	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3097 independent reflections
Radiation source: fine-focus sealed tube	2154 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.101
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −19→19
T_min = 0.984, T_max = 0.992	k = −12→12
26346 measured reflections	l = −24→24

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) = 0.195	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0923P)² + 1.1347P] where P = (F_o² + 2F_c²)/3
3097 reflections	(Δ/σ)_max = 0.002
211 parameters	Δρ_max = 0.34 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₂₃N₃O₃	V = 3532.2 (9) Å³
M_r = 317.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.059 (2) Å	µ = 0.08 mm⁻¹
b = 10.6310 (16) Å	T = 292 K
c = 20.690 (3) Å	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3097 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2154 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.992	R_int = 0.101
26346 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	1 restraint
wR(F²) = 0.195	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
3097 reflections	Δρ_min = −0.18 e Å⁻³
211 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	0.09982 (18)	0.7576 (3)	0.08787 (13)	0.0458 (7)
C2	0.0456 (2)	0.6621 (3)	0.06955 (14)	0.0551 (8)
H2	−0.0046	0.6822	0.0496	0.066*
C3	0.0655 (2)	0.5376 (3)	0.08081 (17)	0.0659 (9)
H3	0.0290	0.4745	0.0679	0.079*
C4	0.1392 (2)	0.5062 (3)	0.11101 (15)	0.0603 (9)
H4	0.1525	0.4223	0.1184	0.072*
C5	0.19213 (19)	0.5989 (3)	0.12982 (15)	0.0591 (9)
H5	0.2415	0.5782	0.1508	0.071*
C6	0.17313 (18)	0.7238 (3)	0.11799 (14)	0.0547 (8)
H6	0.2105	0.7861	0.1306	0.066*
C7	0.11827 (17)	0.9583 (3)	0.04646 (12)	0.0424 (7)
C9	0.15621 (18)	1.1546 (3)	0.00999 (13)	0.0479 (7)
C10	0.2068 (2)	1.0674 (3)	−0.09344 (15)	0.0645 (9)
H10A	0.1498	1.0486	−0.1056	0.077*
H10B	0.2182	1.1534	−0.1065	0.077*
C11	0.2631 (3)	0.9824 (5)	−0.13001 (18)	0.0954 (14)
H11	0.2525	0.8962	−0.1153	0.114*
C12	0.3534 (3)	1.0105 (7)	−0.1188 (3)	0.162 (3)
H12A	0.3643	1.0971	−0.1287	0.244*
H12B	0.3868	0.9577	−0.1462	0.244*
H12C	0.3671	0.9944	−0.0744	0.244*
C13	0.2439 (4)	0.9881 (8)	−0.2014 (2)	0.167 (3)
H13A	0.1864	0.9671	−0.2084	0.251*
H13B	0.2786	0.9293	−0.2241	0.251*
H13C	0.2544	1.0716	−0.2172	0.251*
C14	0.02954 (18)	1.1411 (3)	0.07902 (14)	0.0508 (8)
H14A	−0.0183	1.0858	0.0756	0.061*
H14B	0.0147	1.2210	0.0595	0.061*
C15	0.04940 (19)	1.1616 (3)	0.14927 (14)	0.0503 (7)
C16	−0.0116 (3)	1.2182 (4)	0.24988 (18)	0.0879 (13)
H16A	−0.0635	1.1980	0.2714	0.106*
H16B	0.0318	1.1664	0.2687	0.106*
C17	0.0080 (4)	1.3489 (5)	0.2607 (2)	0.1209 (18)
H17A	0.0605	1.3684	0.2409	0.181*
H17B	0.0112	1.3648	0.3063	0.181*
H17C	−0.0347	1.4005	0.2420	0.181*
N1	0.07527 (15)	0.8841 (2)	0.08053 (12)	0.0518 (6)
N2	0.18427 (15)	0.9414 (2)	0.00589 (11)	0.0501 (6)
H2A	0.2208	0.8838	0.0119	0.060*
C8	0.21386 (19)	1.0593 (3)	−0.02093 (13)	0.0492 (7)
H8	0.2715	1.0748	−0.0074	0.059*
N3	0.09884 (14)	1.0867 (2)	0.04362 (11)	0.0444 (6)
O1	0.15797 (13)	1.2674 (2)	0.00413 (11)	0.0635 (6)
O2	0.11634 (16)	1.1560 (3)	0.17248 (12)	0.0920 (9)
O3	−0.01909 (14)	1.1890 (2)	0.18119 (10)	0.0732 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0515 (17)	0.0453 (17)	0.0406 (15)	−0.0024 (14)	0.0101 (13)	0.0044 (12)
C2	0.0557 (18)	0.054 (2)	0.0560 (19)	−0.0059 (15)	−0.0061 (14)	0.0081 (14)
C3	0.068 (2)	0.049 (2)	0.081 (2)	−0.0111 (17)	−0.0014 (18)	0.0035 (17)
C4	0.066 (2)	0.049 (2)	0.066 (2)	0.0048 (16)	0.0110 (17)	0.0138 (15)
C5	0.0473 (18)	0.067 (2)	0.064 (2)	0.0020 (16)	0.0024 (15)	0.0149 (16)
C6	0.0526 (18)	0.058 (2)	0.0531 (18)	−0.0125 (15)	0.0022 (14)	0.0054 (14)
C7	0.0502 (16)	0.0414 (17)	0.0357 (14)	−0.0016 (13)	0.0013 (12)	−0.0010 (12)
C9	0.0526 (17)	0.0422 (18)	0.0489 (16)	−0.0031 (14)	−0.0012 (13)	0.0044 (13)
C10	0.065 (2)	0.075 (2)	0.0532 (19)	−0.0010 (18)	0.0023 (16)	0.0055 (16)
C11	0.104 (3)	0.123 (4)	0.059 (2)	0.020 (3)	0.009 (2)	−0.007 (2)
C12	0.090 (4)	0.305 (10)	0.091 (3)	0.043 (5)	0.022 (3)	−0.007 (4)
C13	0.157 (5)	0.282 (9)	0.063 (3)	0.058 (5)	0.006 (3)	−0.046 (4)
C14	0.0510 (17)	0.0511 (18)	0.0502 (17)	0.0098 (14)	0.0016 (14)	−0.0031 (13)
C15	0.0499 (18)	0.0472 (18)	0.0538 (18)	0.0065 (14)	0.0047 (15)	0.0007 (13)
C16	0.097 (3)	0.110 (3)	0.057 (2)	−0.003 (2)	0.026 (2)	−0.010 (2)
C17	0.191 (5)	0.101 (4)	0.071 (3)	−0.014 (4)	0.018 (3)	−0.024 (2)
N1	0.0576 (15)	0.0453 (15)	0.0525 (14)	−0.0005 (12)	0.0111 (12)	0.0061 (11)
N2	0.0576 (15)	0.0439 (14)	0.0488 (14)	0.0064 (11)	0.0124 (11)	0.0031 (11)
C8	0.0517 (17)	0.0482 (18)	0.0477 (16)	−0.0010 (14)	0.0101 (13)	0.0053 (13)
N3	0.0521 (14)	0.0361 (13)	0.0449 (13)	0.0010 (11)	0.0068 (11)	−0.0007 (10)
O1	0.0723 (15)	0.0399 (14)	0.0782 (15)	−0.0001 (10)	0.0046 (12)	0.0065 (11)
O2	0.0664 (16)	0.145 (3)	0.0649 (16)	0.0304 (17)	−0.0104 (13)	−0.0237 (15)
O3	0.0633 (15)	0.0986 (19)	0.0576 (14)	0.0068 (13)	0.0157 (11)	−0.0164 (12)

Geometric parameters (Å, º) top

C1—C6	1.380 (4)	C11—H11	0.9800
C1—C2	1.391 (4)	C12—H12A	0.9600
C1—N1	1.410 (4)	C12—H12B	0.9600
C2—C3	1.381 (5)	C12—H12C	0.9600
C2—H2	0.9300	C13—H13A	0.9600
C3—C4	1.378 (5)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.358 (5)	C14—N3	1.453 (3)
C4—H4	0.9300	C14—C15	1.504 (4)
C5—C6	1.385 (4)	C14—H14A	0.9700
C5—H5	0.9300	C14—H14B	0.9700
C6—H6	0.9300	C15—O2	1.179 (3)
C7—N1	1.263 (3)	C15—O3	1.316 (3)
C7—N2	1.364 (3)	C16—C17	1.441 (6)
C7—N3	1.401 (3)	C16—O3	1.460 (4)
C9—O1	1.205 (3)	C16—H16A	0.9700
C9—N3	1.362 (4)	C16—H16B	0.9700
C9—C8	1.514 (4)	C17—H17A	0.9600
C10—C11	1.485 (5)	C17—H17B	0.9600
C10—C8	1.507 (4)	C17—H17C	0.9600
C10—H10A	0.9700	N2—C8	1.451 (4)
C10—H10B	0.9700	N2—H2A	0.8573
C11—C12	1.499 (7)	C8—H8	0.9800
C11—C13	1.511 (6)

C6—C1—C2	117.8 (3)	C11—C13—H13A	109.5
C6—C1—N1	122.4 (3)	C11—C13—H13B	109.5
C2—C1—N1	119.5 (3)	H13A—C13—H13B	109.5
C3—C2—C1	120.6 (3)	C11—C13—H13C	109.5
C3—C2—H2	119.7	H13A—C13—H13C	109.5
C1—C2—H2	119.7	H13B—C13—H13C	109.5
C4—C3—C2	120.5 (3)	N3—C14—C15	112.5 (2)
C4—C3—H3	119.8	N3—C14—H14A	109.1
C2—C3—H3	119.8	C15—C14—H14A	109.1
C5—C4—C3	119.4 (3)	N3—C14—H14B	109.1
C5—C4—H4	120.3	C15—C14—H14B	109.1
C3—C4—H4	120.3	H14A—C14—H14B	107.8
C4—C5—C6	120.5 (3)	O2—C15—O3	124.7 (3)
C4—C5—H5	119.8	O2—C15—C14	125.4 (3)
C6—C5—H5	119.8	O3—C15—C14	109.9 (3)
C1—C6—C5	121.2 (3)	C17—C16—O3	111.9 (3)
C1—C6—H6	119.4	C17—C16—H16A	109.2
C5—C6—H6	119.4	O3—C16—H16A	109.2
N1—C7—N2	133.3 (3)	C17—C16—H16B	109.2
N1—C7—N3	120.6 (2)	O3—C16—H16B	109.2
N2—C7—N3	106.0 (2)	H16A—C16—H16B	107.9
O1—C9—N3	126.5 (3)	C16—C17—H17A	109.5
O1—C9—C8	127.5 (3)	C16—C17—H17B	109.5
N3—C9—C8	105.9 (2)	H17A—C17—H17B	109.5
C11—C10—C8	115.3 (3)	C16—C17—H17C	109.5
C11—C10—H10A	108.5	H17A—C17—H17C	109.5
C8—C10—H10A	108.5	H17B—C17—H17C	109.5
C11—C10—H10B	108.5	C7—N1—C1	120.2 (2)
C8—C10—H10B	108.5	C7—N2—C8	112.1 (2)
H10A—C10—H10B	107.5	C7—N2—H2A	122.5
C10—C11—C12	112.9 (4)	C8—N2—H2A	116.7
C10—C11—C13	110.5 (4)	N2—C8—C10	113.9 (3)
C12—C11—C13	109.9 (4)	N2—C8—C9	102.5 (2)
C10—C11—H11	107.8	C10—C8—C9	109.7 (2)
C12—C11—H11	107.8	N2—C8—H8	110.2
C13—C11—H11	107.8	C10—C8—H8	110.2
C11—C12—H12A	109.5	C9—C8—H8	110.2
C11—C12—H12B	109.5	C9—N3—C7	112.8 (2)
H12A—C12—H12B	109.5	C9—N3—C14	124.3 (2)
C11—C12—H12C	109.5	C7—N3—C14	122.5 (2)
H12A—C12—H12C	109.5	C15—O3—C16	117.8 (3)
H12B—C12—H12C	109.5

C6—C1—C2—C3	−0.7 (4)	C11—C10—C8—N2	−68.4 (4)
N1—C1—C2—C3	−175.0 (3)	C11—C10—C8—C9	177.5 (3)
C1—C2—C3—C4	0.7 (5)	O1—C9—C8—N2	177.5 (3)
C2—C3—C4—C5	0.1 (5)	N3—C9—C8—N2	−5.4 (3)
C3—C4—C5—C6	−1.0 (5)	O1—C9—C8—C10	−61.2 (4)
C2—C1—C6—C5	−0.2 (4)	N3—C9—C8—C10	115.9 (3)
N1—C1—C6—C5	174.0 (3)	O1—C9—N3—C7	−174.2 (3)
C4—C5—C6—C1	1.0 (5)	C8—C9—N3—C7	8.6 (3)
C8—C10—C11—C12	−62.8 (5)	O1—C9—N3—C14	−0.6 (5)
C8—C10—C11—C13	173.7 (4)	C8—C9—N3—C14	−177.7 (2)
N3—C14—C15—O2	12.5 (5)	N1—C7—N3—C9	173.8 (3)
N3—C14—C15—O3	−168.6 (3)	N2—C7—N3—C9	−8.3 (3)
N2—C7—N1—C1	8.7 (5)	N1—C7—N3—C14	0.1 (4)
N3—C7—N1—C1	−174.1 (2)	N2—C7—N3—C14	177.9 (2)
C6—C1—N1—C7	63.9 (4)	C15—C14—N3—C9	−94.3 (3)
C2—C1—N1—C7	−122.0 (3)	C15—C14—N3—C7	78.7 (3)
N1—C7—N2—C8	−178.2 (3)	O2—C15—O3—C16	1.9 (5)
N3—C7—N2—C8	4.3 (3)	C14—C15—O3—C16	−177.1 (3)
C7—N2—C8—C10	−117.7 (3)	C17—C16—O3—C15	85.4 (5)
C7—N2—C8—C9	0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.47	3.257 (4)	143
N2—H2A···O1ⁱ	0.86	2.31	3.137 (3)	162

Symmetry code: (i) −x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃N₃O₃
M_r	317.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	292
a, b, c (Å)	16.059 (2), 10.6310 (16), 20.690 (3)
V (Å³)	3532.2 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.984, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	26346, 3097, 2154
R_int	0.101
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.195, 1.06
No. of reflections	3097
No. of parameters	211
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.18

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2ⁱ	0.93	2.47	3.257 (4)	142.6
N2—H2A···O1ⁱ	0.86	2.31	3.137 (3)	161.5

Symmetry code: (i) −x+1/2, y−1/2, z.

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Ethyl 2-[(Z)-4-isobutyl-5-oxo-2-(phenyl­imino)imidazolidin-1-yl]acetate

Supporting information

Key indicators

checkCIF/PLATON results

Ethyl 2-[(Z)-4-isobutyl-5-oxo-2-(phenylimino)imidazolidin-1-yl]acetate