3-Chloro-4-dimethyl-amino-5-[(1R,2S,5R)-2-isopropyl-5-methyl-cyclo-hex-yloxy]furan-2(5H)-one.

The title compound, C(16)H(26)ClNO(3) contains one almost planar furan-one ring [maximum deviation of 0.021 (2) Å for the O atom] with a stereogenic center (S) and one cyclo-hexane ring which displays a chair conformation and has three stereogenic centers [S at the C atom bearing the isopropyl group, R at the C atom attached to the O atom and R at the C atom bearing the methyl group].

Related literature

For natural products containing a 2(5H)-furan­one subunit, see: Ming et al. (2002 ▶). For biologically active 2(5H)-furan­ones, see: Bailly et al. (2008 ▶). For the synthesis of 2(5H)-furan­ones with substituents in positions 3 and 4, see: Van Oeveren et al. (1994 ▶); For related structures, see: Chen et al. (1995 ▶); Martín & Mateo (1995 ▶); Gawronski et al. (1997 ▶). For the use of benzimidazoles in organic synthesis, see: Mao et al. (2010 ▶). For standard bond lengths, see: Allen et al. (1987 ▶); Orpen et al. (1989 ▶). For the structures of heterosubstituted 2(5H)-furan­ones, see: Gawronski et al. (1997 ▶). For the synthesis and structure of optically pure 5-(l-menth­yloxy)-3,4-dichloro-2(5H)-furan­one, see: Chen & Geng (1993 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C16H26ClNO3

M = 315.83

Orthorhombic,

a = 7.5438 (5) Å

b = 8.1631 (5) Å

c = 28.5953 (17) Å

V = 1760.92 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.23 × 0.22 × 0.19 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.950, T max = 0.958

9112 measured reflections

2922 independent reflections

1951 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.117

S = 1.02

2922 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Absolute structure: Flack (1983 ▶), 1066 Friedel pairs

Flack parameter: −0.05 (9)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015583/si2350sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015583/si2350Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015583/si2350Isup3.cml

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

C16H26ClNO3	F(000) = 680
Mr = 315.83	Dx = 1.191 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3099 reflections
a = 7.5438 (5) Å	θ = 2.8–20.5°
b = 8.1631 (5) Å	µ = 0.23 mm−1
c = 28.5953 (17) Å	T = 296 K
V = 1760.92 (19) Å3	Block, colourless
Z = 4	0.23 × 0.22 × 0.19 mm

Bruker APEXII area-detector diffractometer	2922 independent reflections
Radiation source: fine-focus sealed tube	1951 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 25.2°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.950, Tmax = 0.958	k = −9→6
9112 measured reflections	l = −23→34

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.047	w = 1/[σ2(Fo2) + (0.055P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.117	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.15 e Å−3
2922 reflections	Δρmin = −0.14 e Å−3
196 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.016 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1066 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: −0.05 (9)

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.

	x	y	z	Uiso*/Ueq
C1	0.4580 (5)	0.8674 (4)	0.45480 (10)	0.0785 (11)
H1A	0.3934	0.7827	0.4714	0.094*
H1B	0.5740	0.8773	0.4691	0.094*
C2	0.4806 (4)	0.8152 (4)	0.40327 (9)	0.0628 (9)
H2	0.5491	0.9020	0.3880	0.075*
C3	0.2995 (4)	0.8133 (3)	0.37990 (9)	0.0525 (8)
H3	0.2272	0.7270	0.3942	0.063*
C4	0.2051 (5)	0.9754 (3)	0.38525 (9)	0.0701 (10)
H4A	0.0895	0.9685	0.3705	0.084*
H4B	0.2724	1.0599	0.3693	0.084*
C5	0.1815 (6)	1.0237 (4)	0.43669 (11)	0.0804 (11)
H5	0.1112	0.9379	0.4519	0.096*
C6	0.3610 (7)	1.0271 (4)	0.45991 (11)	0.0893 (12)
H6A	0.4316	1.1140	0.4462	0.107*
H6B	0.3462	1.0514	0.4929	0.107*
C7	0.0799 (7)	1.1841 (5)	0.44127 (12)	0.1207 (16)
H7A	0.0713	1.2137	0.4737	0.181*
H7B	−0.0369	1.1710	0.4285	0.181*
H7C	0.1413	1.2688	0.4245	0.181*
C8	0.5869 (5)	0.6562 (4)	0.39706 (11)	0.0718 (10)
H8	0.5775	0.6257	0.3640	0.086*
C9	0.5161 (5)	0.5122 (4)	0.42518 (12)	0.0989 (14)
H9A	0.5293	0.5345	0.4580	0.148*
H9B	0.5814	0.4151	0.4173	0.148*
H9C	0.3930	0.4960	0.4181	0.148*
C10	0.7855 (5)	0.6823 (6)	0.40726 (13)	0.1098 (14)
H10A	0.8276	0.7752	0.3899	0.165*
H10B	0.8507	0.5865	0.3981	0.165*
H10C	0.8019	0.7016	0.4401	0.165*
C11	0.2476 (5)	0.4116 (4)	0.31317 (11)	0.0793 (11)
H11A	0.3620	0.3966	0.3272	0.119*
H11B	0.1923	0.3069	0.3087	0.119*
H11C	0.1751	0.4777	0.3333	0.119*
C12	0.3298 (6)	0.3891 (4)	0.23027 (11)	0.0928 (12)
H12A	0.2355	0.3726	0.2082	0.139*
H12B	0.3670	0.2853	0.2426	0.139*
H12C	0.4280	0.4411	0.2149	0.139*
C13	0.2303 (4)	0.6503 (3)	0.26159 (9)	0.0495 (7)
C14	0.2256 (4)	0.7458 (3)	0.22286 (9)	0.0530 (8)
C15	0.1758 (4)	0.9092 (4)	0.23489 (11)	0.0588 (8)
C16	0.1844 (4)	0.7605 (3)	0.30258 (10)	0.0529 (8)
H16	0.0818	0.7180	0.3198	0.063*
Cl1	0.26385 (14)	0.70164 (12)	0.16516 (3)	0.0940 (4)
N1	0.2678 (3)	0.4928 (3)	0.26825 (8)	0.0609 (7)
O1	0.3317 (3)	0.7719 (2)	0.33142 (6)	0.0524 (5)
O2	0.1456 (3)	0.9169 (2)	0.28218 (6)	0.0627 (6)
O3	0.1584 (3)	1.0295 (3)	0.21086 (7)	0.0817 (7)

	U11	U22	U33	U12	U13	U23
C1	0.098 (3)	0.095 (3)	0.0424 (19)	−0.022 (2)	−0.0045 (19)	−0.0019 (18)
C2	0.075 (3)	0.077 (2)	0.0371 (18)	−0.022 (2)	−0.0020 (17)	0.0055 (15)
C3	0.062 (2)	0.0594 (16)	0.0362 (16)	−0.0128 (16)	0.0064 (15)	−0.0012 (12)
C4	0.095 (3)	0.0667 (18)	0.0485 (18)	−0.0030 (19)	0.0067 (19)	−0.0073 (14)
C5	0.116 (4)	0.075 (2)	0.050 (2)	0.001 (2)	0.010 (2)	−0.0140 (16)
C6	0.137 (4)	0.086 (2)	0.045 (2)	−0.017 (3)	0.002 (2)	−0.0115 (18)
C7	0.174 (4)	0.106 (3)	0.082 (3)	0.036 (3)	0.010 (3)	−0.038 (2)
C8	0.070 (3)	0.093 (3)	0.053 (2)	−0.005 (2)	−0.0094 (19)	0.0014 (18)
C9	0.118 (4)	0.096 (3)	0.083 (3)	0.003 (3)	−0.010 (3)	0.025 (2)
C10	0.069 (3)	0.178 (4)	0.083 (3)	−0.002 (3)	−0.016 (2)	0.003 (3)
C11	0.090 (3)	0.0654 (17)	0.082 (2)	0.004 (2)	−0.013 (2)	0.0145 (17)
C12	0.101 (3)	0.078 (2)	0.099 (3)	0.025 (2)	−0.005 (2)	−0.029 (2)
C13	0.047 (2)	0.0554 (16)	0.0464 (16)	−0.0003 (15)	−0.0049 (16)	−0.0037 (14)
C14	0.052 (2)	0.0640 (17)	0.0426 (18)	−0.0003 (15)	−0.0025 (15)	−0.0071 (14)
C15	0.052 (2)	0.0674 (19)	0.057 (2)	−0.0010 (17)	−0.0063 (18)	0.0047 (17)
C16	0.057 (2)	0.0535 (16)	0.0482 (17)	−0.0012 (15)	−0.0009 (17)	−0.0027 (14)
Cl1	0.1203 (10)	0.1131 (7)	0.0485 (5)	0.0028 (6)	0.0062 (5)	−0.0091 (4)
N1	0.065 (2)	0.0527 (13)	0.0646 (16)	0.0081 (13)	−0.0033 (15)	−0.0077 (12)
O1	0.0491 (14)	0.0721 (11)	0.0360 (10)	−0.0039 (10)	−0.0030 (10)	−0.0042 (9)
O2	0.0772 (17)	0.0524 (11)	0.0586 (14)	0.0124 (11)	−0.0053 (12)	−0.0035 (10)
O3	0.0903 (19)	0.0725 (13)	0.0823 (16)	0.0021 (13)	−0.0102 (15)	0.0247 (12)

C1—C6	1.502 (5)	C9—H9A	0.9600
C1—C2	1.544 (4)	C9—H9B	0.9600
C1—H1A	0.9700	C9—H9C	0.9600
C1—H1B	0.9700	C10—H10A	0.9600
C2—C3	1.521 (4)	C10—H10B	0.9600
C2—C8	1.536 (5)	C10—H10C	0.9600
C2—H2	0.9800	C11—N1	1.453 (3)
C3—O1	1.447 (3)	C11—H11A	0.9600
C3—C4	1.511 (4)	C11—H11B	0.9600
C3—H3	0.9800	C11—H11C	0.9600
C4—C5	1.533 (4)	C12—N1	1.454 (4)
C4—H4A	0.9700	C12—H12A	0.9600
C4—H4B	0.9700	C12—H12B	0.9600
C5—C6	1.509 (6)	C12—H12C	0.9600
C5—C7	1.523 (5)	C13—N1	1.331 (3)
C5—H5	0.9800	C13—C14	1.354 (3)
C6—H6A	0.9700	C13—C16	1.518 (4)
C6—H6B	0.9700	C14—C15	1.428 (4)
C7—H7A	0.9600	C14—Cl1	1.713 (3)
C7—H7B	0.9600	C15—O3	1.205 (3)
C7—H7C	0.9600	C15—O2	1.373 (3)
C8—C9	1.521 (4)	C16—O1	1.387 (3)
C8—C10	1.541 (5)	C16—O2	1.434 (3)
C8—H8	0.9800	C16—H16	0.9800
C6—C1—C2	112.7 (3)	C2—C8—H8	106.8
C6—C1—H1A	109.0	C10—C8—H8	106.8
C2—C1—H1A	109.0	C8—C9—H9A	109.5
C6—C1—H1B	109.0	C8—C9—H9B	109.5
C2—C1—H1B	109.0	H9A—C9—H9B	109.5
H1A—C1—H1B	107.8	C8—C9—H9C	109.5
C3—C2—C8	114.2 (3)	H9A—C9—H9C	109.5
C3—C2—C1	108.8 (3)	H9B—C9—H9C	109.5
C8—C2—C1	113.7 (3)	C8—C10—H10A	109.5
C3—C2—H2	106.5	C8—C10—H10B	109.5
C8—C2—H2	106.5	H10A—C10—H10B	109.5
C1—C2—H2	106.5	C8—C10—H10C	109.5
O1—C3—C4	112.3 (2)	H10A—C10—H10C	109.5
O1—C3—C2	105.8 (2)	H10B—C10—H10C	109.5
C4—C3—C2	111.7 (3)	N1—C11—H11A	109.5
O1—C3—H3	109.0	N1—C11—H11B	109.5
C4—C3—H3	109.0	H11A—C11—H11B	109.5
C2—C3—H3	109.0	N1—C11—H11C	109.5
C3—C4—C5	112.1 (2)	H11A—C11—H11C	109.5
C3—C4—H4A	109.2	H11B—C11—H11C	109.5
C5—C4—H4A	109.2	N1—C12—H12A	109.5
C3—C4—H4B	109.2	N1—C12—H12B	109.5
C5—C4—H4B	109.2	H12A—C12—H12B	109.5
H4A—C4—H4B	107.9	N1—C12—H12C	109.5
C6—C5—C7	113.5 (3)	H12A—C12—H12C	109.5
C6—C5—C4	108.8 (3)	H12B—C12—H12C	109.5
C7—C5—C4	111.2 (3)	N1—C13—C14	132.7 (3)
C6—C5—H5	107.7	N1—C13—C16	120.7 (2)
C7—C5—H5	107.7	C14—C13—C16	106.5 (2)
C4—C5—H5	107.7	C13—C14—C15	110.3 (2)
C1—C6—C5	112.2 (3)	C13—C14—Cl1	131.5 (2)
C1—C6—H6A	109.2	C15—C14—Cl1	118.2 (2)
C5—C6—H6A	109.2	O3—C15—O2	120.4 (3)
C1—C6—H6B	109.2	O3—C15—C14	130.7 (3)
C5—C6—H6B	109.2	O2—C15—C14	108.9 (2)
H6A—C6—H6B	107.9	O1—C16—O2	110.2 (2)
C5—C7—H7A	109.5	O1—C16—C13	108.4 (2)
C5—C7—H7B	109.5	O2—C16—C13	105.1 (2)
H7A—C7—H7B	109.5	O1—C16—H16	111.0
C5—C7—H7C	109.5	O2—C16—H16	111.0
H7A—C7—H7C	109.5	C13—C16—H16	111.0
H7B—C7—H7C	109.5	C13—N1—C11	123.0 (2)
C9—C8—C2	114.1 (3)	C13—N1—C12	121.6 (3)
C9—C8—C10	110.4 (3)	C11—N1—C12	115.4 (2)
C2—C8—C10	111.6 (3)	C16—O1—C3	116.8 (2)
C9—C8—H8	106.8	C15—O2—C16	109.0 (2)