(E)-Methyl 2-chloro-4-dicyclo­hexyl­amino-4-oxobut-2-enoate

Liu, C.-M.; Xue, F.-L.; Fu, J.-H.; Wang, Z.-Y.

doi:10.1107/S1600536811027760

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2051

doi:10.1107/S1600536811027760

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(E)-Methyl 2-chloro-4-dicyclohexylamino-4-oxobut-2-enoate

Cai-Mei Liu,^a Fu-Ling Xue,^a Jian-Hua Fu ^a and Zhao-Yang Wang ^a ^*

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: wangwangzhaoyang@tom.com

(Received 11 May 2011; accepted 11 July 2011; online 16 July 2011)

In the title compound, C₁₇H₂₆ClNO₃, both cyclohexyl rings have chair conformations. In the crystal, molecules are linked by weak intermolecular 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_r = 327.84
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.053
wR(F²) = 0.160
S = 1.02
3886 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811027760/lx2191sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811027760/lx2191Isup3.cml

checkCIF report

Comment top

Molecules possessing 2(5H)-furanone moiety are useful heterocyclic compounds due to their valuable biological activities such as antibacterial, anti-inflammatory and antitumor (Lattmann et al., 2005; Rowland et al., 2007; Kim et al., 2002). The 5-alkoxy-3,4-dihalo-2(5H)-furanones being a kind of synthons are widely used in tandem Michael addition-elimination reactions (Song et al., 2009). The 4-amino-2(5H)-furanones exhibit an antibiotic activity against MRSA (Lattmann et al., 1999; Lattmann et al., 2006). Therefore, we are interested in the tandem Michael addition-elimination reaction of the synthon 3,4-dichloro-5-methoxyfuran-2(5H)-one with secondary amines in the present of potassium fluoride. However, we obtained an unanticipated product, (E)-methyl 2-chloro-4-(dicyclohexylamino)-4-oxobut-2-enoate, instead of the expected compound 3-chloro-4-(dicyclohexylamino)-5-methoxyfuran-2(5H)-one (Lattmann et al., 1999). Herein, we report the crystal structure of the title compound.

In the title compound (Fig. 1), the both cyclohexyl rings are in the chair form. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between the H atom of the vinyl group and the O atom of the ester group (Table 1; C9—H9···O2ⁱⁱ), and a methyl H atom and the O atom of the amide group (Table 1; C17—H17A···O1ⁱ).

Related literature top

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 their antibiotic activity, see: Kimura et al. (2000); Tanoury et al. (2008). For related structures, see: Lattmann et al. (1999, 2006).

Experimental top

The precursor 3,4-dichloro-5-methoxyfuran-2(5H)-one was prepared according to the literature procedure (Song et al., 2009). The solution of dicyclohexylamine (2.736 g, 3.0 mL) in tetrahydrofuran (3.0 mL) was added to a stirred solution of 3,4-dichloro-5-methoxyfuran-(5H)-one (36.39 mg, 2.0 mmol) and potassium fluoride (34.85 mg, 6.0 mmol) in tetrahydrofuran (3.0 mL) under nitrogen atmosphere. After being stirred at room temperature for 24 h, the solvent was removed under reduced pressure. The residual solid was dissolved in dichloromethane and then the combined organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with the gradient mixture of petroleum ether and ethyl acetate to give the title compound (yield 22.6%). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in (insert proper solvent) at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. [Symmetry codes: (i) - x + 2, - y + 1, - z; (ii) - x + 2, y + 1/2, - z + 1/2; (iii) - x + 2, y - 1/2, - z + 1/2.]

(E)-Methyl 2-chloro-4-dicyclohexylamino-4-oxobut-2-enoate top

Crystal data top

C₁₇H₂₆ClNO₃	F(000) = 704
M_r = 327.84	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.070P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
3886 reflections	Δρ_max = 0.24 e Å⁻³
201 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₂₆ClNO₃	V = 1777.5 (6) Å³
M_r = 327.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8291 (19) Å	µ = 0.23 mm⁻¹
b = 10.533 (2) Å	T = 298 K
c = 19.139 (4) Å	0.32 × 0.22 × 0.20 mm
β = 92.955 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	3886 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2457 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.956	R_int = 0.051
8635 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
3886 reflections	Δρ_min = −0.28 e Å⁻³
201 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+1, −z; (ii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₆ClNO₃
M_r	327.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.8291 (19), 10.533 (2), 19.139 (4)
β (°)	92.955 (3)
V (Å³)	1777.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.32 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.931, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	8635, 3886, 2457
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.160, 1.02
No. of reflections	3886
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···O1ⁱ	0.96	2.44	3.323 (4)	152.6
C9—H9···O2ⁱⁱ	0.93	2.50	3.389 (3)	160.0

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

Acknowledgements

This work was supported by the National Natural Science Foundation of China (grant No. 20772035) and the Natural Science Foundation of Guangdong Province, China (grant No. 5300082).

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