(E)-Methyl 2-chloro-4-dicyclo-hexyl-amino-4-oxobut-2-enoate.

In the title compound, C(17)H(26)ClNO(3), both cyclo-hexyl rings have chair conformations. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the synthesis, see: Song et al. (2009 ▶). For the biological activity of 2(5H)-furan­ones, see: Lattmann et al. (2005 ▶); Rowland et al. (2007 ▶); Kim et al. (2002 ▶). For chemical, pharmaceutical and agrochemical applications of 3,4-amino-2(5H)-furanones, see: Kimura et al. (2000 ▶); Tanoury et al. (2008 ▶). For related structures, see: Lattmann et al. (1999 ▶, 2006 ▶).

Experimental

Crystal data

C17H26ClNO3

M = 327.84

Monoclinic,

a = 8.8291 (19) Å

b = 10.533 (2) Å

c = 19.139 (4) Å

β = 92.955 (3)°

V = 1777.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 298 K

0.32 × 0.22 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.931, T max = 0.956

8635 measured reflections

3886 independent reflections

2457 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.160

S = 1.02

3886 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811027760/lx2191sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811027760/lx2191Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811027760/lx2191Isup3.cml

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

C17H26ClNO3	F(000) = 704
Mr = 327.84	Dx = 1.225 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2253 reflections
a = 8.8291 (19) Å	θ = 2.2–23.5°
b = 10.533 (2) Å	µ = 0.23 mm−1
c = 19.139 (4) Å	T = 298 K
β = 92.955 (3)°	Block, colourless
V = 1777.5 (6) Å3	0.32 × 0.22 × 0.20 mm
Z = 4

Bruker APEXII area-detector diffractometer	3886 independent reflections
Radiation source: fine-focus sealed tube	2457 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.1°
φ and ω scans	h = −4→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→12
Tmin = 0.931, Tmax = 0.956	l = −24→24
8635 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053	H-atom parameters constrained
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3886 reflections	Δρmax = 0.24 e Å−3
201 parameters	Δρmin = −0.28 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (3)

Experimental. Data for (I): 1H NMR (400 MHz, CDCl3, TMS): 1.073-1.564 (12H, m, 6CH2), 1.681-2.436 (8H, m, 4CH2), 2.973-3.124 (1H, m, CH), 3.350-3.417 (1H, m, CH), 3.813 (3H, s, CH3), ESI-MS, m/z (%): Calcd for C17H27ClNO3+([M+H]+): 328.16(100.0), 330.16(32.6), found: 328.39(15.0), 330.43(5.0).

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.

	x	y	z	Uiso*/Ueq
Cl1	1.02330 (7)	0.47301 (6)	0.29004 (3)	0.0574 (2)
N1	0.7284 (2)	0.73071 (19)	0.10932 (8)	0.0427 (5)
C1	0.6049 (2)	0.7104 (2)	0.15716 (10)	0.0452 (6)
H1	0.6483	0.6628	0.1974	0.054*
C6	0.4768 (3)	0.6305 (3)	0.12475 (14)	0.0623 (7)
H6A	0.4338	0.6728	0.0833	0.075*
H6B	0.5167	0.5492	0.1105	0.075*
C3	0.4221 (3)	0.8114 (3)	0.23589 (14)	0.0711 (8)
H3A	0.4656	0.7696	0.2774	0.085*
H3B	0.3815	0.8924	0.2501	0.085*
C2	0.5460 (3)	0.8343 (3)	0.18519 (12)	0.0588 (7)
H2A	0.5062	0.8861	0.1465	0.071*
H2B	0.6288	0.8804	0.2088	0.071*
C4	0.2953 (3)	0.7311 (3)	0.20438 (14)	0.0662 (8)
H4A	0.2238	0.7126	0.2398	0.079*
H4B	0.2421	0.7781	0.1671	0.079*
C5	0.3537 (3)	0.6090 (3)	0.17577 (18)	0.0805 (9)
H5A	0.2704	0.5633	0.1523	0.097*
H5B	0.3937	0.5568	0.2142	0.097*
C9	0.9064 (2)	0.6357 (2)	0.19601 (10)	0.0407 (5)
H9	0.9020	0.6907	0.2338	0.049*
C10	0.9445 (2)	0.5170 (2)	0.20899 (10)	0.0414 (5)
C8	0.8696 (2)	0.6886 (2)	0.12389 (10)	0.0431 (5)
C7	0.6909 (3)	0.7947 (2)	0.04169 (10)	0.0469 (6)
H7	0.5843	0.8202	0.0426	0.056*
C11	0.9352 (3)	0.4105 (2)	0.15775 (11)	0.0519 (6)
C12	0.7807 (3)	0.9153 (3)	0.03266 (13)	0.0625 (7)
H12A	0.8878	0.8952	0.0320	0.075*
H12B	0.7662	0.9716	0.0718	0.075*
C16	0.7013 (3)	0.7045 (3)	−0.02024 (11)	0.0617 (7)
H16A	0.6369	0.6312	−0.0140	0.074*
H16B	0.8049	0.6752	−0.0233	0.074*
C13	0.7293 (4)	0.9818 (3)	−0.03560 (14)	0.0788 (10)
H13A	0.6254	1.0104	−0.0327	0.095*
H13B	0.7924	1.0557	−0.0423	0.095*
C15	0.6504 (4)	0.7749 (4)	−0.08734 (13)	0.0845 (11)
H15A	0.6612	0.7190	−0.1271	0.101*
H15B	0.5439	0.7967	−0.0855	0.101*
C14	0.7399 (4)	0.8930 (4)	−0.09763 (14)	0.0881 (12)
H14A	0.7018	0.9357	−0.1399	0.106*
H14B	0.8452	0.8710	−0.1033	0.106*
O1	0.97348 (18)	0.69654 (19)	0.08431 (8)	0.0573 (5)
O3	0.8279 (2)	0.43037 (19)	0.10887 (9)	0.0648 (5)
O2	1.0144 (3)	0.3193 (2)	0.16138 (10)	0.0985 (9)
C17	0.8142 (4)	0.3387 (4)	0.05276 (16)	0.0938 (11)
H17A	0.8939	0.3520	0.0213	0.141*
H17B	0.7177	0.3487	0.0279	0.141*
H17C	0.8218	0.2545	0.0718	0.141*

	U11	U22	U33	U12	U13	U23
Cl1	0.0631 (4)	0.0582 (4)	0.0499 (3)	0.0121 (3)	−0.0066 (3)	0.0093 (2)
N1	0.0360 (10)	0.0521 (12)	0.0399 (9)	0.0072 (8)	0.0010 (7)	0.0075 (7)
C1	0.0338 (11)	0.0604 (16)	0.0417 (11)	0.0065 (10)	0.0025 (8)	0.0121 (10)
C6	0.0532 (15)	0.0544 (18)	0.0806 (17)	−0.0074 (12)	0.0148 (13)	−0.0088 (13)
C3	0.0494 (15)	0.105 (3)	0.0594 (14)	−0.0008 (15)	0.0108 (12)	−0.0137 (15)
C2	0.0438 (13)	0.0717 (19)	0.0617 (14)	−0.0059 (12)	0.0110 (11)	−0.0175 (12)
C4	0.0413 (14)	0.084 (2)	0.0744 (17)	0.0032 (13)	0.0129 (12)	0.0066 (14)
C5	0.0538 (17)	0.071 (2)	0.118 (2)	−0.0079 (15)	0.0236 (16)	0.0114 (17)
C9	0.0358 (11)	0.0439 (14)	0.0422 (10)	0.0024 (9)	−0.0014 (8)	−0.0004 (9)
C10	0.0362 (11)	0.0462 (14)	0.0417 (10)	0.0056 (9)	0.0023 (8)	0.0038 (9)
C8	0.0410 (12)	0.0448 (14)	0.0434 (11)	0.0036 (10)	−0.0004 (9)	−0.0023 (9)
C7	0.0440 (12)	0.0558 (15)	0.0408 (10)	0.0090 (11)	0.0004 (9)	0.0082 (9)
C11	0.0612 (15)	0.0469 (15)	0.0486 (12)	0.0088 (12)	0.0128 (11)	0.0018 (10)
C12	0.0655 (17)	0.0614 (19)	0.0607 (14)	0.0049 (14)	0.0044 (12)	0.0136 (12)
C16	0.0622 (16)	0.078 (2)	0.0440 (12)	0.0043 (14)	−0.0025 (11)	−0.0009 (11)
C13	0.081 (2)	0.079 (2)	0.0781 (19)	0.0246 (17)	0.0235 (16)	0.0392 (16)
C15	0.080 (2)	0.129 (3)	0.0432 (13)	0.022 (2)	−0.0034 (13)	0.0081 (15)
C14	0.092 (2)	0.119 (3)	0.0547 (15)	0.040 (2)	0.0198 (15)	0.0367 (17)
O1	0.0416 (9)	0.0774 (14)	0.0534 (9)	0.0111 (8)	0.0070 (7)	0.0084 (8)
O3	0.0602 (11)	0.0674 (13)	0.0654 (10)	0.0056 (9)	−0.0101 (9)	−0.0238 (9)
O2	0.150 (2)	0.0773 (17)	0.0678 (12)	0.0605 (16)	−0.0023 (13)	−0.0091 (10)
C17	0.107 (3)	0.096 (3)	0.0781 (19)	0.003 (2)	−0.0031 (18)	−0.0433 (18)

Cl1—C10	1.730 (2)	C8—O1	1.222 (2)
N1—C8	1.339 (3)	C7—C12	1.512 (4)
N1—C1	1.475 (3)	C7—C16	1.525 (3)
N1—C7	1.481 (3)	C7—H7	0.9800
C1—C2	1.514 (4)	C11—O2	1.189 (3)
C1—C6	1.517 (3)	C11—O3	1.313 (3)
C1—H1	0.9800	C12—C13	1.530 (3)
C6—C5	1.515 (3)	C12—H12A	0.9700
C6—H6A	0.9700	C12—H12B	0.9700
C6—H6B	0.9700	C16—C15	1.530 (4)
C3—C4	1.504 (4)	C16—H16A	0.9700
C3—C2	1.518 (3)	C16—H16B	0.9700
C3—H3A	0.9700	C13—C14	1.518 (5)
C3—H3B	0.9700	C13—H13A	0.9700
C2—H2A	0.9700	C13—H13B	0.9700
C2—H2B	0.9700	C15—C14	1.493 (5)
C4—C5	1.500 (4)	C15—H15A	0.9700
C4—H4A	0.9700	C15—H15B	0.9700
C4—H4B	0.9700	C14—H14A	0.9700
C5—H5A	0.9700	C14—H14B	0.9700
C5—H5B	0.9700	O3—C17	1.444 (3)
C9—C10	1.315 (3)	C17—H17A	0.9600
C9—C8	1.508 (3)	C17—H17B	0.9600
C9—H9	0.9300	C17—H17C	0.9600
C10—C11	1.489 (3)
C8—N1—C1	122.19 (17)	N1—C8—C9	117.89 (18)
C8—N1—C7	119.78 (17)	N1—C7—C12	112.77 (19)
C1—N1—C7	117.97 (16)	N1—C7—C16	112.1 (2)
N1—C1—C2	111.9 (2)	C12—C7—C16	112.4 (2)
N1—C1—C6	112.71 (18)	N1—C7—H7	106.3
C2—C1—C6	111.2 (2)	C12—C7—H7	106.3
N1—C1—H1	106.9	C16—C7—H7	106.3
C2—C1—H1	106.9	O2—C11—O3	124.8 (2)
C6—C1—H1	106.9	O2—C11—C10	123.9 (2)
C5—C6—C1	111.3 (2)	O3—C11—C10	111.3 (2)
C5—C6—H6A	109.4	C7—C12—C13	110.4 (2)
C1—C6—H6A	109.4	C7—C12—H12A	109.6
C5—C6—H6B	109.4	C13—C12—H12A	109.6
C1—C6—H6B	109.4	C7—C12—H12B	109.6
H6A—C6—H6B	108.0	C13—C12—H12B	109.6
C4—C3—C2	112.3 (2)	H12A—C12—H12B	108.1
C4—C3—H3A	109.2	C7—C16—C15	108.9 (2)
C2—C3—H3A	109.2	C7—C16—H16A	109.9
C4—C3—H3B	109.2	C15—C16—H16A	109.9
C2—C3—H3B	109.2	C7—C16—H16B	109.9
H3A—C3—H3B	107.9	C15—C16—H16B	109.9
C1—C2—C3	111.2 (2)	H16A—C16—H16B	108.3
C1—C2—H2A	109.4	C14—C13—C12	111.0 (2)
C3—C2—H2A	109.4	C14—C13—H13A	109.4
C1—C2—H2B	109.4	C12—C13—H13A	109.4
C3—C2—H2B	109.4	C14—C13—H13B	109.4
H2A—C2—H2B	108.0	C12—C13—H13B	109.4
C5—C4—C3	111.5 (2)	H13A—C13—H13B	108.0
C5—C4—H4A	109.3	C14—C15—C16	112.3 (3)
C3—C4—H4A	109.3	C14—C15—H15A	109.1
C5—C4—H4B	109.3	C16—C15—H15A	109.1
C3—C4—H4B	109.3	C14—C15—H15B	109.1
H4A—C4—H4B	108.0	C16—C15—H15B	109.1
C4—C5—C6	112.2 (3)	H15A—C15—H15B	107.9
C4—C5—H5A	109.2	C15—C14—C13	110.9 (2)
C6—C5—H5A	109.2	C15—C14—H14A	109.5
C4—C5—H5B	109.2	C13—C14—H14A	109.5
C6—C5—H5B	109.2	C15—C14—H14B	109.5
H5A—C5—H5B	107.9	C13—C14—H14B	109.5
C10—C9—C8	124.41 (19)	H14A—C14—H14B	108.1
C10—C9—H9	117.8	C11—O3—C17	116.9 (2)
C8—C9—H9	117.8	O3—C17—H17A	109.5
C9—C10—C11	125.92 (19)	O3—C17—H17B	109.5
C9—C10—Cl1	120.73 (17)	H17A—C17—H17B	109.5
C11—C10—Cl1	113.26 (17)	O3—C17—H17C	109.5
O1—C8—N1	124.64 (19)	H17A—C17—H17C	109.5
O1—C8—C9	117.33 (19)	H17B—C17—H17C	109.5
C8—N1—C1—C2	116.2 (2)	C10—C9—C8—N1	115.7 (3)
C7—N1—C1—C2	−66.8 (3)	C8—N1—C7—C12	−61.9 (3)
C8—N1—C1—C6	−117.6 (2)	C1—N1—C7—C12	121.0 (2)
C7—N1—C1—C6	59.4 (3)	C8—N1—C7—C16	66.2 (3)
N1—C1—C6—C5	178.7 (2)	C1—N1—C7—C16	−110.9 (2)
C2—C1—C6—C5	−54.7 (3)	C9—C10—C11—O2	152.5 (3)
N1—C1—C2—C3	−178.38 (19)	Cl1—C10—C11—O2	−23.9 (3)
C6—C1—C2—C3	54.6 (3)	C9—C10—C11—O3	−28.0 (3)
C4—C3—C2—C1	−54.5 (3)	Cl1—C10—C11—O3	155.65 (17)
C2—C3—C4—C5	53.9 (4)	N1—C7—C12—C13	−176.0 (2)
C3—C4—C5—C6	−53.9 (3)	C16—C7—C12—C13	56.0 (3)
C1—C6—C5—C4	54.5 (3)	N1—C7—C16—C15	176.1 (2)
C8—C9—C10—C11	−10.0 (4)	C12—C7—C16—C15	−55.7 (3)
C8—C9—C10—Cl1	166.08 (16)	C7—C12—C13—C14	−55.2 (3)
C1—N1—C8—O1	175.6 (2)	C7—C16—C15—C14	56.3 (3)
C7—N1—C8—O1	−1.4 (4)	C16—C15—C14—C13	−57.4 (3)
C1—N1—C8—C9	−8.9 (3)	C12—C13—C14—C15	56.2 (4)
C7—N1—C8—C9	174.2 (2)	O2—C11—O3—C17	−5.0 (4)
C10—C9—C8—O1	−68.4 (3)	C10—C11—O3—C17	175.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O1i	0.96	2.44	3.323 (4)	153.
C9—H9···O2ii	0.93	2.50	3.389 (3)	160.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17A⋯O1i	0.96	2.44	3.323 (4)	153
C9—H9⋯O2ii	0.93	2.50	3.389 (3)	160

Symmetry codes: (i) ; (ii) .