(S)-3-Bromo-4-diallyl­amino-5-[(1R,2S,5R)-2-isopropyl-5-methyl­cyclo­hex­yloxy]furan-2(5H)-one

Fu, J.-H.; Wang, Z.-Y.; Li, J.-X.; Tan, Y.-H.

doi:10.1107/S1600536810047173

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3277

https://doi.org/10.1107/S1600536810047173

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(S)-3-Bromo-4-diallylamino-5-[(1R,2S,5R)-2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one

Jian-Hua Fu,^a Zhao-Yang Wang,^a ^* Jian-Xiao Li ^a and Yue-He Tan ^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 November 2010; accepted 14 November 2010; online 24 November 2010)

The title compound, C₂₀H₃₀BrNO₃, was obtained via a tandem asymmetric Michael addition–elimination reaction of 3,4-dibromo-5-(S)-(l-menthyloxy)-2(5H)-furanone and diallylamine in the presence of potassium fluoride. In the molecule, the five-membered furanone ring is approximately planar [maximum atomic deviation = 0.030 (3) Å], and the six-membered cyclohexane ring adopts a chair conformation.

Related literature

The title compound is a derivative of 4-amino-2(5H)-furanone. For the biological activity of 4-amino-2(5H)-furanones, see: Gondela & Walczak (2010 ); Tanoury et al. (2008 ); Kimura et al. (2000 ). For asymmetric Michael addition reactions of 2(5H)-furanone, see: Hoffmann et al. (2006 ); He et al. (2006). For the synthesis of the title compound, see: Song et al. (2009 ).

Experimental

Crystal data

C₂₀H₃₀BrNO₃
M_r = 412.35
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.5215 (16) Å
b = 11.934 (2) Å
c = 20.603 (4) Å
V = 2095.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 1.98 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.16 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.641, T_max = 0.729
19608 measured reflections
3640 independent reflections
2660 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.075
S = 1.04
3640 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1543 Friedel pairs
Flack parameter: 0.001 (9)

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: https://doi.org/10.1107/S1600536810047173/xu5089sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810047173/xu5089Isup2.hkl

checkCIF report

Comment top

The 2(5H)-furanone moiety occurs in many natural products exhibiting various biological activities, namely antibiotic cytotoxic and antitumor (Gondela et al., 2010). Recently, owing to their specific activity and high stereoselectivity, chiral 5-S-(l-menthyloxy)-2(5H)-furanones have emerged as significant synthetic intermediates (Hoffmann et al., 2006; Song et al., 2009). At the same time, 4-amino-2(5H)-furanone (or 3-amino-2(5H)-furanone) is an attractive moiety in chemical, pharmaceutical and agrochemical research (Tanoury et al., 2008; Kimura et al., 2000).

Therefore we are interested in the tandem Michael addition-elimination reaction of the chiral synthon 3,4-dibromo-5-(S)-(l-menthyloxy)-2(5H)-furanone and diallylamine in the present of potassium fluoride. The structure of the title compound (I) is illustrated in Fig. 1. The crystal structure of the title compound which has four chiral centers (C11(S), C9(R), C4(S), C7(R)) contains a five-membered furanone ring and a six-membered rings connected each other via C11—O3—C9 ether bond. The furanone ring of C11—O2—C14—C13—C12 is approximately planar, whereas the six-membered ring displays a chair conformation.

Related literature top

The title compound is a derivative of the 4-amino-2(5H)-furanone. For the biological activity of 4-amino-2(5H)-furanones, see: Gondela et al. (2010); Tanoury et al. (2008); Kimura et al. (2000). For asymmetric Michael addition reactions of 2(5H)-furanone, see: Hoffmann et al. (2006); He et al. (2006). For the synthesis of the title compound, see: Song et al. (2009).

Experimental top

The precursor 3,4-dibromo-5-(S)-(l-menthyloxy)-2(5H)-furanone was prepared according to the literature procedure (Song et al., 2009). After the mixture of 3,4-dibromo-5-(S)-(l-menthyloxy)-2(5H)-furanone (2.0 mmol) and potassium fluoride (6.0 mmol) was dissolved in absolute tetrahydrofuran (2.0 mL) under nitrogen atmosphere, tetrahydrofuran solution of diallylamine (3.0 mmol) was added. The reaction was carried out under the stirring at room temperature for 24 h. Once the reaction was complete, the solvents were removed under reduced pressure. The residual solid was dissolved in dichloromethane. Then the combined organic layers from extraction were concentrated under reduced pressure, and the crude product was purified by silica gel column chromatography with the gradient mixture of petroleum ether and ethyl acetate to give the product yielding (I) 0.645 g (78.3%).

Structure description top

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.
	Fig. 2. Perspective view of the crystal packing.

(S)-3-Bromo-4-diallylamino-5-[(1R,2S,5R)- 2-isopropyl-5-methylcyclohexyloxy]furan-2(5H)-one top

Crystal data top

C₂₀H₃₀BrNO₃	F(000) = 864
M_r = 412.35	D_x = 1.307 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3500 reflections
a = 8.5215 (16) Å	θ = 2.6–20.9°
b = 11.934 (2) Å	µ = 1.98 mm⁻¹
c = 20.603 (4) Å	T = 298 K
V = 2095.2 (7) Å³	Block, colourless
Z = 4	0.23 × 0.20 × 0.16 mm

Data collection top

Bruker APEXII area-detector diffractometer	3640 independent reflections
Radiation source: fine-focus sealed tube	2660 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
φ and ω scan	θ_max = 24.9°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.641, T_max = 0.729	k = −14→14
19608 measured reflections	l = −24→24

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.075	w = 1/[σ²(F_o²) + (0.P)² + 0.1072P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3640 reflections	Δρ_max = 0.28 e Å⁻³
230 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1543 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.001 (9)

Crystal data top

C₂₀H₃₀BrNO₃	V = 2095.2 (7) Å³
M_r = 412.35	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.5215 (16) Å	µ = 1.98 mm⁻¹
b = 11.934 (2) Å	T = 298 K
c = 20.603 (4) Å	0.23 × 0.20 × 0.16 mm

Data collection top

Bruker APEXII area-detector diffractometer	3640 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2660 reflections with I > 2σ(I)
T_min = 0.641, T_max = 0.729	R_int = 0.078
19608 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.075	Δρ_max = 0.28 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
3640 reflections	Absolute structure: Flack (1983), 1543 Friedel pairs
230 parameters	Absolute structure parameter: 0.001 (9)
0 restraints

Special details top

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
Br1	0.27706 (5)	−0.04364 (3)	0.92085 (2)	0.07258 (18)
O3	0.2972 (3)	0.36270 (16)	0.96994 (9)	0.0435 (5)
O2	0.3680 (3)	0.21670 (19)	1.03849 (10)	0.0574 (7)
O1	0.2726 (3)	0.0470 (2)	1.06339 (12)	0.0797 (8)
C4	0.2198 (4)	0.5548 (3)	0.97362 (17)	0.0567 (9)
H4	0.1129	0.5295	0.9834	0.068*
C9	0.3298 (4)	0.4689 (3)	1.00221 (16)	0.0479 (9)
H9	0.4381	0.4911	0.9927	0.057*
C8	0.3107 (4)	0.4579 (3)	1.07491 (17)	0.0579 (8)
H8A	0.3878	0.4051	1.0911	0.070*
H8B	0.2074	0.4277	1.0842	0.070*
C6	0.2203 (5)	0.6563 (3)	1.0818 (2)	0.0822 (12)
H6A	0.1126	0.6350	1.0907	0.099*
H6B	0.2394	0.7284	1.1021	0.099*
C3	0.2302 (4)	0.5667 (3)	0.89958 (18)	0.0670 (11)
H3	0.2262	0.4906	0.8819	0.080*
C5	0.2427 (5)	0.6670 (3)	1.0096 (2)	0.0798 (13)
H5A	0.3476	0.6949	1.0010	0.096*
H5B	0.1685	0.7214	0.9928	0.096*
C2	0.3854 (5)	0.6182 (4)	0.8759 (2)	0.0923 (14)
H2A	0.3909	0.6952	0.8892	0.138*
H2B	0.3903	0.6140	0.8294	0.138*
H2C	0.4719	0.5776	0.8943	0.138*
C10	0.3028 (6)	0.5538 (4)	1.1835 (2)	0.1184 (18)
H10A	0.1984	0.5261	1.1906	0.178*
H10B	0.3154	0.6243	1.2054	0.178*
H10C	0.3774	0.5009	1.2003	0.178*
C7	0.3301 (4)	0.5697 (3)	1.1109 (2)	0.0727 (12)
H7	0.4382	0.5956	1.1046	0.087*
C12	0.3881 (3)	0.1916 (2)	0.92585 (17)	0.0411 (7)
C11	0.4052 (4)	0.2769 (3)	0.98021 (15)	0.0441 (8)
H11	0.5124	0.3065	0.9819	0.053*
C13	0.3321 (4)	0.0962 (3)	0.95381 (17)	0.0468 (9)
C14	0.3192 (4)	0.1112 (3)	1.02266 (19)	0.0557 (10)
N1	0.4230 (3)	0.2185 (2)	0.86442 (14)	0.0512 (8)
C16	0.6441 (5)	0.3143 (3)	0.81261 (19)	0.0658 (11)
H16	0.7254	0.2830	0.8366	0.079*
C17	0.6743 (6)	0.3435 (3)	0.7539 (2)	0.0898 (14)
H17A	0.5960	0.3751	0.7283	0.108*
H17B	0.7744	0.3329	0.7369	0.108*
C15	0.4897 (4)	0.3267 (3)	0.84513 (18)	0.0547 (10)
H15A	0.5020	0.3734	0.8833	0.066*
H15B	0.4175	0.3642	0.8159	0.066*
C18	0.3789 (5)	0.1460 (3)	0.81058 (17)	0.0659 (11)
H18A	0.3965	0.0687	0.8231	0.079*
H18B	0.4467	0.1620	0.7739	0.079*
C19	0.2127 (6)	0.1588 (4)	0.7897 (2)	0.0828 (13)
H19	0.1814	0.1184	0.7534	0.099*
C20	0.1081 (6)	0.2206 (4)	0.8173 (2)	0.0991 (16)
H20A	0.1340	0.2626	0.8538	0.119*
H20B	0.0067	0.2232	0.8006	0.119*
C1	0.0902 (5)	0.6287 (4)	0.8715 (2)	0.0987 (16)
H1A	0.0917	0.7051	0.8861	0.148*
H1B	−0.0049	0.5934	0.8857	0.148*
H1C	0.0954	0.6269	0.8250	0.148*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0696 (3)	0.0426 (2)	0.1055 (3)	−0.0069 (2)	0.0069 (2)	−0.0098 (2)
O3	0.0464 (13)	0.0334 (11)	0.0508 (13)	0.0051 (11)	0.0006 (11)	−0.0065 (10)
O2	0.0797 (18)	0.0465 (14)	0.0460 (15)	0.0092 (13)	0.0040 (13)	0.0029 (12)
O1	0.1046 (19)	0.0580 (15)	0.0766 (18)	0.0109 (18)	0.0256 (16)	0.0173 (14)
C4	0.050 (2)	0.0383 (18)	0.082 (3)	−0.001 (2)	0.008 (2)	−0.0055 (17)
C9	0.0412 (19)	0.0343 (18)	0.068 (3)	−0.0073 (16)	0.0054 (16)	−0.0098 (17)
C8	0.055 (2)	0.054 (2)	0.065 (2)	0.0018 (19)	0.002 (2)	−0.011 (2)
C6	0.071 (3)	0.054 (2)	0.122 (4)	−0.005 (2)	0.011 (3)	−0.039 (2)
C3	0.071 (3)	0.046 (2)	0.084 (3)	0.004 (2)	0.012 (2)	0.0154 (17)
C5	0.073 (3)	0.040 (2)	0.126 (4)	0.000 (2)	0.007 (3)	−0.012 (2)
C2	0.094 (4)	0.068 (3)	0.115 (4)	0.001 (3)	0.031 (3)	0.028 (3)
C10	0.141 (4)	0.129 (4)	0.085 (4)	0.017 (4)	0.002 (3)	−0.060 (3)
C7	0.057 (2)	0.071 (3)	0.090 (3)	−0.001 (2)	0.007 (2)	−0.039 (2)
C12	0.0338 (17)	0.0386 (18)	0.051 (2)	0.0041 (13)	0.0021 (18)	−0.0023 (18)
C11	0.046 (2)	0.0382 (18)	0.048 (2)	0.0053 (16)	0.0020 (17)	−0.0017 (17)
C13	0.048 (2)	0.0388 (19)	0.053 (2)	0.0103 (16)	0.0032 (17)	−0.0003 (16)
C14	0.055 (3)	0.039 (2)	0.073 (3)	0.0175 (18)	0.015 (2)	0.0080 (19)
N1	0.0573 (19)	0.0478 (17)	0.048 (2)	−0.0038 (15)	0.0100 (15)	−0.0076 (15)
C16	0.070 (3)	0.067 (3)	0.061 (3)	−0.006 (2)	0.006 (2)	0.009 (2)
C17	0.107 (4)	0.082 (3)	0.081 (3)	0.005 (3)	0.018 (3)	0.021 (2)
C15	0.065 (3)	0.046 (2)	0.054 (2)	−0.0049 (18)	0.007 (2)	−0.0010 (17)
C18	0.084 (3)	0.064 (3)	0.050 (2)	−0.014 (2)	0.010 (2)	−0.015 (2)
C19	0.086 (3)	0.097 (3)	0.065 (3)	−0.024 (3)	−0.017 (3)	0.003 (2)
C20	0.070 (3)	0.125 (4)	0.103 (4)	−0.011 (3)	−0.018 (3)	0.037 (4)
C1	0.099 (4)	0.086 (3)	0.111 (4)	0.017 (3)	0.003 (3)	0.030 (3)

Geometric parameters (Å, º) top

Br1—C13	1.862 (3)	C10—H10A	0.9600
O3—C11	1.393 (4)	C10—H10B	0.9600
O3—C9	1.458 (3)	C10—H10C	0.9600
O2—C14	1.365 (4)	C7—H7	0.9800
O2—C11	1.434 (4)	C12—N1	1.339 (4)
O1—C14	1.204 (4)	C12—C13	1.362 (4)
C4—C9	1.509 (4)	C12—C11	1.521 (4)
C4—C3	1.535 (5)	C11—H11	0.9800
C4—C5	1.542 (4)	C13—C14	1.434 (5)
C4—H4	0.9800	N1—C18	1.456 (4)
C9—C8	1.512 (4)	N1—C15	1.466 (4)
C9—H9	0.9800	C16—C17	1.285 (5)
C8—C7	1.535 (5)	C16—C15	1.484 (5)
C8—H8A	0.9700	C16—H16	0.9300
C8—H8B	0.9700	C17—H17A	0.9300
C6—C5	1.505 (5)	C17—H17B	0.9300
C6—C7	1.518 (5)	C15—H15A	0.9700
C6—H6A	0.9700	C15—H15B	0.9700
C6—H6B	0.9700	C18—C19	1.488 (6)
C3—C1	1.518 (5)	C18—H18A	0.9700
C3—C2	1.538 (5)	C18—H18B	0.9700
C3—H3	0.9800	C19—C20	1.288 (6)
C5—H5A	0.9700	C19—H19	0.9300
C5—H5B	0.9700	C20—H20A	0.9300
C2—H2A	0.9600	C20—H20B	0.9300
C2—H2B	0.9600	C1—H1A	0.9600
C2—H2C	0.9600	C1—H1B	0.9600
C10—C7	1.526 (6)	C1—H1C	0.9600

C11—O3—C9	116.3 (2)	C10—C7—C8	110.4 (3)
C14—O2—C11	109.2 (3)	C6—C7—H7	108.2
C9—C4—C3	114.5 (3)	C10—C7—H7	108.2
C9—C4—C5	108.9 (3)	C8—C7—H7	108.2
C3—C4—C5	112.9 (3)	N1—C12—C13	132.7 (3)
C9—C4—H4	106.7	N1—C12—C11	120.9 (3)
C3—C4—H4	106.7	C13—C12—C11	106.3 (3)
C5—C4—H4	106.7	O3—C11—O2	110.5 (3)
O3—C9—C4	107.1 (2)	O3—C11—C12	108.5 (2)
O3—C9—C8	110.9 (3)	O2—C11—C12	105.1 (2)
C4—C9—C8	112.3 (3)	O3—C11—H11	110.9
O3—C9—H9	108.8	O2—C11—H11	110.9
C4—C9—H9	108.8	C12—C11—H11	110.9
C8—C9—H9	108.8	C12—C13—C14	109.9 (3)
C9—C8—C7	113.1 (3)	C12—C13—Br1	133.1 (3)
C9—C8—H8A	109.0	C14—C13—Br1	117.0 (2)
C7—C8—H8A	109.0	O1—C14—O2	121.4 (3)
C9—C8—H8B	109.0	O1—C14—C13	129.4 (3)
C7—C8—H8B	109.0	O2—C14—C13	109.2 (3)
H8A—C8—H8B	107.8	C12—N1—C18	121.3 (3)
C5—C6—C7	111.8 (3)	C12—N1—C15	123.6 (3)
C5—C6—H6A	109.3	C18—N1—C15	114.7 (3)
C7—C6—H6A	109.3	C17—C16—C15	125.1 (4)
C5—C6—H6B	109.3	C17—C16—H16	117.4
C7—C6—H6B	109.3	C15—C16—H16	117.4
H6A—C6—H6B	107.9	C16—C17—H17A	120.0
C1—C3—C4	112.2 (3)	C16—C17—H17B	120.0
C1—C3—C2	111.1 (3)	H17A—C17—H17B	120.0
C4—C3—C2	113.7 (3)	N1—C15—C16	112.2 (3)
C1—C3—H3	106.4	N1—C15—H15A	109.2
C4—C3—H3	106.4	C16—C15—H15A	109.2
C2—C3—H3	106.4	N1—C15—H15B	109.2
C6—C5—C4	112.7 (3)	C16—C15—H15B	109.2
C6—C5—H5A	109.1	H15A—C15—H15B	107.9
C4—C5—H5A	109.1	N1—C18—C19	113.9 (4)
C6—C5—H5B	109.1	N1—C18—H18A	108.8
C4—C5—H5B	109.1	C19—C18—H18A	108.8
H5A—C5—H5B	107.8	N1—C18—H18B	108.8
C3—C2—H2A	109.5	C19—C18—H18B	108.8
C3—C2—H2B	109.5	H18A—C18—H18B	107.7
H2A—C2—H2B	109.5	C20—C19—C18	126.2 (5)
C3—C2—H2C	109.5	C20—C19—H19	116.9
H2A—C2—H2C	109.5	C18—C19—H19	116.9
H2B—C2—H2C	109.5	C19—C20—H20A	120.0
C7—C10—H10A	109.5	C19—C20—H20B	120.0
C7—C10—H10B	109.5	H20A—C20—H20B	120.0
H10A—C10—H10B	109.5	C3—C1—H1A	109.5
C7—C10—H10C	109.5	C3—C1—H1B	109.5
H10A—C10—H10C	109.5	H1A—C1—H1B	109.5
H10B—C10—H10C	109.5	C3—C1—H1C	109.5
C6—C7—C10	112.2 (3)	H1A—C1—H1C	109.5
C6—C7—C8	109.5 (3)	H1B—C1—H1C	109.5

C11—O3—C9—C4	168.3 (2)	C13—C12—C11—O3	−113.1 (3)
C11—O3—C9—C8	−68.9 (3)	N1—C12—C11—O2	−176.3 (3)
C3—C4—C9—O3	−56.2 (3)	C13—C12—C11—O2	5.0 (3)
C5—C4—C9—O3	176.3 (3)	N1—C12—C13—C14	178.5 (3)
C3—C4—C9—C8	−178.1 (3)	C11—C12—C13—C14	−3.0 (4)
C5—C4—C9—C8	54.4 (4)	N1—C12—C13—Br1	0.3 (6)
O3—C9—C8—C7	−175.2 (3)	C11—C12—C13—Br1	178.8 (3)
C4—C9—C8—C7	−55.4 (4)	C11—O2—C14—O1	−175.5 (3)
C9—C4—C3—C1	164.3 (3)	C11—O2—C14—C13	3.6 (4)
C5—C4—C3—C1	−70.3 (4)	C12—C13—C14—O1	178.8 (3)
C9—C4—C3—C2	−68.5 (4)	Br1—C13—C14—O1	−2.6 (5)
C5—C4—C3—C2	56.9 (4)	C12—C13—C14—O2	−0.2 (4)
C7—C6—C5—C4	57.1 (4)	Br1—C13—C14—O2	178.3 (2)
C9—C4—C5—C6	−55.9 (4)	C13—C12—N1—C18	10.4 (5)
C3—C4—C5—C6	175.7 (3)	C11—C12—N1—C18	−167.9 (3)
C5—C6—C7—C10	−177.1 (3)	C13—C12—N1—C15	−177.2 (3)
C5—C6—C7—C8	−54.0 (4)	C11—C12—N1—C15	4.5 (5)
C9—C8—C7—C6	53.5 (4)	C12—N1—C15—C16	120.4 (3)
C9—C8—C7—C10	177.6 (3)	C18—N1—C15—C16	−66.7 (4)
C9—O3—C11—O2	85.9 (3)	C17—C16—C15—N1	117.8 (4)
C9—O3—C11—C12	−159.4 (2)	C12—N1—C18—C19	80.9 (4)
C14—O2—C11—O3	111.6 (3)	C15—N1—C18—C19	−92.2 (4)
C14—O2—C11—C12	−5.2 (3)	N1—C18—C19—C20	−4.7 (7)
N1—C12—C11—O3	65.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20A···N1	0.93	2.53	2.854 (6)	101
C18—H18A···Br1	0.97	2.62	3.322 (4)	129
C15—H15A···O3	0.97	2.50	3.081 (4)	118
C8—H8A···O2	0.97	2.50	3.015 (4)	113
C3—H3···O3	0.98	2.45	2.891 (4)	107

Experimental details

Crystal data
Chemical formula	C₂₀H₃₀BrNO₃
M_r	412.35
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	8.5215 (16), 11.934 (2), 20.603 (4)
V (Å³)	2095.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.98
Crystal size (mm)	0.23 × 0.20 × 0.16

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.641, 0.729
No. of measured, independent and observed [I > 2σ(I)] reflections	19608, 3640, 2660
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.592

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.075, 1.04
No. of reflections	3640
No. of parameters	230
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21
Absolute structure	Flack (1983), 1543 Friedel pairs
Absolute structure parameter	0.001 (9)

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

Acknowledgements

The 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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