(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butano­yl}-1,3-oxazolidin-2-one

Börding, S.; Strohmann, C.; Preut, H.; Hiersemann, M.

doi:10.1107/S1600536811053840

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o169

doi:10.1107/S1600536811053840

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(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]butanoyl}-1,3-oxazolidin-2-one

Sandra Börding,^a Carsten Strohmann,^a Hans Preut ^a ^* and Martin Hiersemann ^a

^aFakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, 44221 Dortmund, Germany
^*Correspondence e-mail: hans.preut@tu-dortmund.de

(Received 28 November 2011; accepted 14 December 2011; online 17 December 2011)

The title compound, C₁₉H₂₄ClNO₅, was synthesized and subsequently employed in an Evans alkylation. The purpose was to prove the absolute configuration in the projected synthesis of the side chain of (–)-Lytophilippine A. The oxazolidinone and the isopropylidene acetal rings have twisted conformations. The oxazolidinone and side-chain carbonyl groups are orientated in an antiperiplanar arrangement to minimize van der Waals repulsions. Furthermore, the Cl atom and the acetonide-protected secondary alcohol are also in an antiperiplanar arrangement with a torsion angle of 173.64 (14)°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary.

Related literature

For background to the synthesis, see: Gille & Hiersemann (2010 ); Jang et al. (2011 ); Řezanka et al. (2004 ). For Evans alkylation, see: Evans et al. (1981 , 1982 ).

Experimental

Crystal data

C₁₉H₂₄ClNO₅
M_r = 381.84
Monoclinic, P 2₁
a = 11.7552 (9) Å
b = 5.9139 (4) Å
c = 13.8789 (11) Å
β = 109.023 (9)°
V = 912.16 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.910, T_max = 0.954
6562 measured reflections
3594 independent reflections
2515 reflections with I > 2s(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.047
S = 0.98
3594 reflections
237 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1198 Friedel pairs
Flack parameter: 0.11 (5)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811053840/ff2045sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811053840/ff2045Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811053840/ff2045Isup3.cml

checkCIF report

Comment top

The title compound I was obtained during the synthesis of the side chain of (–)-Lytophilippine A (Řezanka et al., 2004). Recently our research group published the synthesis of the core fragment of (–)-Lytophilippine A (Gille & Hiersemann, 2010). Shortly after, the first total synthesis of the postulated structure was published (Jang et al., 2011). Compound I was synthesized and subsequently applied in an Evans alkylation (Evans et al., 1981; Evans et al., 1982) to install the stereogenic center at C23. The synthesis of I was carried out from carboxylic acid and (R)-4-benzyloxazolidin-2-one.

The oxazolidinone ring adopts a nearly coplanar conformation and the isopropylidene acetal is an open envelope-like structure. The oxazolidinone- and side-chain carbonyl groups are orientated in an antiperiplanar arrangement to minimize van der Waals repulsions. The dihedral angle between the plane through N, C10, O2 and the plane through N, C11, O3 is 9.4 (4)°. Furthermore, the chlorine atom and the acetonide protected secondary alcohol are also in an antiperiplanar arrangement with an torsion angle of 173.64 (14)°. The absolute configuration was determined and agrees with the configuration of the used chiral auxiliary.

Related literature top

For background to the synthesis, see: Gille & Hiersemann (2010); Jang et al. (2011); Řezanka et al. (2004). For Evans alkylation, see: Evans et al. (1981, 1982).

Experimental top

To a solution of carboxylic acid (840 mg, 3.77 mmol, 1.0 eq) in THF (20 ml, 5 ml/mmol) was added Et₃N (1.14 ml, 8.15 mmol, 2.0 eq) and pivaloylchloride (0.6 ml, 4.89 mmol, 1.2 eq) at 253 K. After stirring at this temperature for 2 h the mixture was warmed to 273 K. Solid LiCl (240 mg, 5.67 mmol, 1.5 eq) and (R)-4-benzyloxazolidin-2-one (669 mg, 3.77 mmol, 1.0 eq) were added. The reaction was quenched with H₂O after stirring for 2 h at room temperature. The layers were separated and the aqueous phase extracted with Et₂O. The combined organic phases were dried over anhydrous MgSO₄, filtered and concentrated under reduced pressure. Flash column chromatography (cyclohexane/ethyl acetate 5/1) afforded the title compound (1.12 g, 2.93 mmol, 84%) as a thick colourless oil. Single crystals of (I) were obtained by crystallization from isohexane to provide white needles. R_f 0.43 (cyclohexane/ethyl acetate 2/1); Anal. Calcd. for C₁₉H₂₄ClNO₅: C,59.8; H, 6.3; N, 3.7; Found: C, 59.8; H, 6.5; N, 3.6; [α]_D²⁰ -51.4 (c 1.02, CH₃Cl); M = 381.85 g/mol.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the labelling of all non-H atoms. Displacement ellipsoids are shown at the 30% probability level.

(4R)-4-Benzyl-3-{(4S)-4-chloro-4-[(S)-2,2- dimethyl-1,3-dioxolan-4-yl]butanoyl}-1,3-oxazolidin-2-one top

Crystal data top

C₁₉H₂₄ClNO₅	F(000) = 404
M_r = 381.84	D_x = 1.390 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2793 reflections
a = 11.7552 (9) Å	θ = 2.8–29.0°
b = 5.9139 (4) Å	µ = 0.24 mm⁻¹
c = 13.8789 (11) Å	T = 173 K
β = 109.023 (9)°	Block, white
V = 912.16 (12) Å³	0.40 × 0.20 × 0.20 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3594 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2515 reflections with I > 2s(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 16.0560 pixels mm^-1	θ_max = 26.0°, θ_min = 2.8°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −7→7
T_min = 0.910, T_max = 0.954	l = −17→16
6562 measured reflections

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.047	w = 1/[σ²(F_o²) + (0.007P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max < 0.001
3594 reflections	Δρ_max = 0.22 e Å⁻³
237 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1198 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.11 (5)

Crystal data top

C₁₉H₂₄ClNO₅	V = 912.16 (12) Å³
M_r = 381.84	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.7552 (9) Å	µ = 0.24 mm⁻¹
b = 5.9139 (4) Å	T = 173 K
c = 13.8789 (11) Å	0.40 × 0.20 × 0.20 mm
β = 109.023 (9)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	3594 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	2515 reflections with I > 2s(I)
T_min = 0.910, T_max = 0.954	R_int = 0.033
6562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.047	Δρ_max = 0.22 e Å⁻³
S = 0.98	Δρ_min = −0.21 e Å⁻³
3594 reflections	Absolute structure: Flack (1983), 1198 Friedel pairs
237 parameters	Absolute structure parameter: 0.11 (5)
1 restraint

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2008), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.1657 (2)	−0.3801 (4)	0.17220 (18)	0.0189 (6)
C2	0.0920 (2)	−0.2107 (4)	0.18929 (18)	0.0224 (7)
H2	0.1267	−0.0727	0.2202	0.027*
C3	−0.0317 (2)	−0.2418 (4)	0.1616 (2)	0.0290 (7)
H3	−0.0810	−0.1269	0.1750	0.035*
C4	−0.0827 (2)	−0.4398 (4)	0.11451 (19)	0.0270 (7)
H4	−0.1675	−0.4598	0.0940	0.032*
C5	−0.0110 (2)	−0.6085 (4)	0.0972 (2)	0.0285 (7)
H5	−0.0459	−0.7454	0.0653	0.034*
C6	0.1125 (2)	−0.5773 (4)	0.12673 (19)	0.0245 (7)
H6	0.1616	−0.6951	0.1153	0.029*
C7	0.30014 (18)	−0.3420 (4)	0.20129 (17)	0.0201 (6)
H7A	0.3425	−0.4887	0.2185	0.024*
H7B	0.3273	−0.2439	0.2623	0.024*
C8	0.3321 (2)	−0.2315 (4)	0.11426 (18)	0.0191 (6)
H8	0.2796	−0.0967	0.0885	0.023*
C9	0.3254 (2)	−0.3926 (4)	0.02582 (19)	0.0312 (7)
H9A	0.2762	−0.5272	0.0279	0.037*
H9B	0.2896	−0.3155	−0.0405	0.037*
C10	0.5254 (2)	−0.3120 (5)	0.10476 (17)	0.0206 (6)
C11	0.4985 (2)	0.0280 (4)	0.20304 (19)	0.0216 (6)
C12	0.6276 (2)	0.0996 (4)	0.2280 (2)	0.0244 (7)
H12A	0.6385	0.1773	0.1684	0.029*
H12B	0.6800	−0.0358	0.2430	0.029*
C13	0.6643 (2)	0.2563 (4)	0.31873 (19)	0.0220 (7)
H13A	0.6713	0.1670	0.3808	0.026*
H13B	0.5995	0.3689	0.3106	0.026*
C14	0.7817 (2)	0.3812 (4)	0.33466 (19)	0.0209 (6)
H14	0.7708	0.4861	0.2758	0.025*
C15	0.8252 (2)	0.5187 (4)	0.43295 (18)	0.0209 (6)
H15	0.9058	0.5866	0.4413	0.025*
C16	0.8292 (2)	0.3846 (4)	0.52813 (18)	0.0244 (6)
H16A	0.8405	0.2212	0.5187	0.029*
H16B	0.8949	0.4389	0.5886	0.029*
C17	0.6855 (2)	0.6563 (4)	0.50682 (18)	0.0229 (6)
C18	0.55163 (18)	0.6806 (5)	0.46026 (17)	0.0278 (6)
H18A	0.5204	0.5595	0.4104	0.042*
H18B	0.5328	0.8275	0.4261	0.042*
H18C	0.5143	0.6706	0.5138	0.042*
C19	0.7398 (2)	0.8166 (4)	0.59485 (18)	0.0272 (7)
H19A	0.7155	0.7708	0.6531	0.041*
H19B	0.7114	0.9706	0.5743	0.041*
H19C	0.8277	0.8121	0.6141	0.041*
Cl	0.90160 (5)	0.18577 (11)	0.33911 (5)	0.03519 (19)
N	0.46002 (17)	−0.1656 (3)	0.14456 (15)	0.0161 (5)
O1	0.44892 (15)	−0.4571 (3)	0.04026 (13)	0.0265 (4)
O2	0.63229 (13)	−0.3207 (3)	0.12130 (12)	0.0242 (4)
O3	0.42567 (14)	0.1337 (3)	0.22968 (13)	0.0314 (5)
O4	0.71441 (14)	0.4278 (2)	0.53829 (13)	0.0204 (4)
O5	0.73891 (12)	0.6923 (3)	0.42756 (11)	0.0231 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0209 (14)	0.0224 (16)	0.0130 (15)	−0.0011 (12)	0.0049 (13)	0.0024 (11)
C2	0.0283 (16)	0.0211 (14)	0.0183 (17)	0.0020 (13)	0.0085 (15)	−0.0011 (12)
C3	0.0288 (17)	0.0318 (17)	0.0305 (19)	0.0072 (14)	0.0151 (16)	−0.0004 (14)
C4	0.0206 (16)	0.0364 (16)	0.0244 (18)	−0.0029 (14)	0.0079 (15)	0.0005 (14)
C5	0.0306 (17)	0.0216 (16)	0.0353 (19)	−0.0098 (14)	0.0132 (16)	−0.0060 (14)
C6	0.0290 (17)	0.0195 (14)	0.0296 (18)	0.0021 (13)	0.0158 (15)	0.0014 (13)
C7	0.0225 (13)	0.0186 (14)	0.0183 (15)	−0.0005 (14)	0.0054 (12)	−0.0032 (12)
C8	0.0156 (14)	0.0228 (14)	0.0176 (16)	0.0021 (11)	0.0038 (13)	−0.0029 (12)
C9	0.0176 (14)	0.0477 (19)	0.0294 (18)	−0.0047 (14)	0.0094 (15)	−0.0112 (14)
C10	0.0278 (14)	0.0202 (13)	0.0131 (14)	−0.0007 (16)	0.0058 (13)	0.0073 (14)
C11	0.0259 (17)	0.0204 (14)	0.0168 (16)	−0.0011 (13)	0.0046 (14)	0.0036 (13)
C12	0.0197 (14)	0.0233 (15)	0.0334 (18)	−0.0028 (12)	0.0132 (14)	−0.0045 (12)
C13	0.0198 (14)	0.0239 (16)	0.0230 (17)	0.0007 (12)	0.0078 (14)	−0.0014 (12)
C14	0.0198 (15)	0.0208 (14)	0.0239 (17)	0.0079 (13)	0.0097 (14)	0.0060 (13)
C15	0.0176 (15)	0.0202 (14)	0.0242 (17)	−0.0038 (12)	0.0058 (14)	−0.0033 (13)
C16	0.0222 (16)	0.0280 (15)	0.0205 (17)	−0.0031 (13)	0.0033 (14)	−0.0005 (13)
C17	0.0277 (14)	0.0224 (15)	0.0215 (16)	−0.0027 (15)	0.0122 (14)	−0.0001 (14)
C18	0.0277 (14)	0.0233 (13)	0.0337 (17)	−0.0015 (16)	0.0116 (14)	0.0011 (15)
C19	0.0309 (17)	0.0260 (15)	0.0279 (18)	−0.0057 (12)	0.0140 (16)	−0.0055 (13)
Cl	0.0234 (4)	0.0399 (4)	0.0430 (5)	0.0074 (4)	0.0119 (4)	−0.0058 (4)
N	0.0116 (12)	0.0175 (12)	0.0205 (14)	0.0006 (9)	0.0070 (11)	−0.0043 (9)
O1	0.0241 (11)	0.0301 (10)	0.0254 (12)	−0.0011 (8)	0.0083 (10)	−0.0127 (9)
O2	0.0193 (8)	0.0274 (9)	0.0273 (11)	0.0067 (10)	0.0096 (8)	−0.0029 (10)
O3	0.0252 (9)	0.0262 (11)	0.0473 (14)	−0.0023 (9)	0.0182 (10)	−0.0133 (9)
O4	0.0215 (11)	0.0197 (9)	0.0234 (11)	0.0000 (9)	0.0120 (9)	0.0040 (8)
O5	0.0296 (10)	0.0209 (9)	0.0241 (10)	0.0017 (10)	0.0158 (9)	0.0022 (10)

Geometric parameters (Å, º) top

C1—C6	1.376 (3)	C11—C12	1.503 (3)
C1—C2	1.394 (3)	C12—C13	1.508 (3)
C1—C7	1.515 (3)	C12—H12A	0.9900
C2—C3	1.390 (3)	C12—H12B	0.9900
C2—H2	0.9500	C13—C14	1.517 (3)
C3—C4	1.379 (3)	C13—H13A	0.9900
C3—H3	0.9500	C13—H13B	0.9900
C4—C5	1.377 (3)	C14—C15	1.526 (3)
C4—H4	0.9500	C14—Cl	1.808 (2)
C5—C6	1.386 (3)	C14—H14	1.0000
C5—H5	0.9500	C15—O5	1.428 (2)
C6—H6	0.9500	C15—C16	1.528 (3)
C7—C8	1.524 (3)	C15—H15	1.0000
C7—H7A	0.9900	C16—O4	1.425 (3)
C7—H7B	0.9900	C16—H16A	0.9900
C8—N	1.476 (3)	C16—H16B	0.9900
C8—C9	1.536 (3)	C17—O4	1.426 (3)
C8—H8	1.0000	C17—O5	1.449 (2)
C9—O1	1.450 (2)	C17—C18	1.500 (3)
C9—H9A	0.9900	C17—C19	1.514 (3)
C9—H9B	0.9900	C18—H18A	0.9800
C10—O2	1.202 (2)	C18—H18B	0.9800
C10—O1	1.350 (3)	C18—H18C	0.9800
C10—N	1.386 (3)	C19—H19A	0.9800
C11—O3	1.211 (2)	C19—H19B	0.9800
C11—N	1.391 (3)	C19—H19C	0.9800

C6—C1—C2	118.2 (2)	C12—C13—C14	114.81 (19)
C6—C1—C7	121.8 (2)	C12—C13—H13A	108.6
C2—C1—C7	120.0 (2)	C14—C13—H13A	108.6
C3—C2—C1	120.7 (2)	C12—C13—H13B	108.6
C3—C2—H2	119.7	C14—C13—H13B	108.6
C1—C2—H2	119.7	H13A—C13—H13B	107.5
C4—C3—C2	119.8 (2)	C13—C14—C15	114.5 (2)
C4—C3—H3	120.1	C13—C14—Cl	110.85 (15)
C2—C3—H3	120.1	C15—C14—Cl	106.22 (17)
C5—C4—C3	120.1 (3)	C13—C14—H14	108.4
C5—C4—H4	120.0	C15—C14—H14	108.4
C3—C4—H4	120.0	Cl—C14—H14	108.4
C4—C5—C6	119.6 (2)	O5—C15—C14	108.09 (19)
C4—C5—H5	120.2	O5—C15—C16	103.84 (17)
C6—C5—H5	120.2	C14—C15—C16	113.78 (18)
C1—C6—C5	121.6 (2)	O5—C15—H15	110.3
C1—C6—H6	119.2	C14—C15—H15	110.3
C5—C6—H6	119.2	C16—C15—H15	110.3
C1—C7—C8	110.94 (19)	O4—C16—C15	103.26 (18)
C1—C7—H7A	109.5	O4—C16—H16A	111.1
C8—C7—H7A	109.5	C15—C16—H16A	111.1
C1—C7—H7B	109.5	O4—C16—H16B	111.1
C8—C7—H7B	109.5	C15—C16—H16B	111.1
H7A—C7—H7B	108.0	H16A—C16—H16B	109.1
N—C8—C7	112.25 (19)	O4—C17—O5	104.61 (18)
N—C8—C9	99.97 (18)	O4—C17—C18	109.5 (2)
C7—C8—C9	113.96 (18)	O5—C17—C18	108.19 (19)
N—C8—H8	110.1	O4—C17—C19	110.5 (2)
C7—C8—H8	110.1	O5—C17—C19	110.32 (19)
C9—C8—H8	110.1	C18—C17—C19	113.3 (2)
O1—C9—C8	105.4 (2)	C17—C18—H18A	109.5
O1—C9—H9A	110.7	C17—C18—H18B	109.5
C8—C9—H9A	110.7	H18A—C18—H18B	109.5
O1—C9—H9B	110.7	C17—C18—H18C	109.5
C8—C9—H9B	110.7	H18A—C18—H18C	109.5
H9A—C9—H9B	108.8	H18B—C18—H18C	109.5
O2—C10—O1	121.9 (3)	C17—C19—H19A	109.5
O2—C10—N	129.2 (3)	C17—C19—H19B	109.5
O1—C10—N	108.97 (19)	H19A—C19—H19B	109.5
O3—C11—N	118.3 (2)	C17—C19—H19C	109.5
O3—C11—C12	123.1 (2)	H19A—C19—H19C	109.5
N—C11—C12	118.6 (2)	H19B—C19—H19C	109.5
C11—C12—C13	110.96 (19)	C10—N—C11	129.0 (2)
C11—C12—H12A	109.4	C10—N—C8	111.57 (19)
C13—C12—H12A	109.4	C11—N—C8	119.42 (19)
C11—C12—H12B	109.4	C10—O1—C9	110.18 (18)
C13—C12—H12B	109.4	C16—O4—C17	106.18 (16)
H12A—C12—H12B	108.0	C15—O5—C17	109.33 (17)

C6—C1—C2—C3	0.4 (4)	O2—C10—N—C11	9.7 (4)
C7—C1—C2—C3	179.0 (2)	O1—C10—N—C11	−170.7 (2)
C1—C2—C3—C4	−1.5 (4)	O2—C10—N—C8	−172.6 (3)
C2—C3—C4—C5	1.5 (4)	O1—C10—N—C8	6.9 (3)
C3—C4—C5—C6	−0.4 (4)	O3—C11—N—C10	179.5 (2)
C2—C1—C6—C5	0.7 (4)	C12—C11—N—C10	0.9 (3)
C7—C1—C6—C5	−177.9 (2)	O3—C11—N—C8	2.0 (3)
C4—C5—C6—C1	−0.7 (4)	C12—C11—N—C8	−176.5 (2)
C6—C1—C7—C8	90.3 (3)	C7—C8—N—C10	104.9 (2)
C2—C1—C7—C8	−88.2 (3)	C9—C8—N—C10	−16.3 (2)
C1—C7—C8—N	172.7 (2)	C7—C8—N—C11	−77.2 (3)
C1—C7—C8—C9	−74.6 (3)	C9—C8—N—C11	161.60 (19)
N—C8—C9—O1	19.2 (2)	O2—C10—O1—C9	−173.6 (2)
C7—C8—C9—O1	−100.7 (2)	N—C10—O1—C9	6.8 (3)
O3—C11—C12—C13	21.4 (3)	C8—C9—O1—C10	−17.1 (2)
N—C11—C12—C13	−160.2 (2)	C15—C16—O4—C17	−35.9 (2)
C11—C12—C13—C14	−166.14 (19)	O5—C17—O4—C16	33.2 (2)
C12—C13—C14—C15	−173.5 (2)	C18—C17—O4—C16	148.95 (19)
C12—C13—C14—Cl	−53.4 (2)	C19—C17—O4—C16	−85.6 (2)
C13—C14—C15—O5	−63.7 (2)	C14—C15—O5—C17	116.1 (2)
Cl—C14—C15—O5	173.64 (14)	C16—C15—O5—C17	−5.0 (2)
C13—C14—C15—C16	51.1 (3)	O4—C17—O5—C15	−16.6 (2)
Cl—C14—C15—C16	−71.6 (2)	C18—C17—O5—C15	−133.4 (2)
O5—C15—C16—O4	24.8 (2)	C19—C17—O5—C15	102.2 (2)
C14—C15—C16—O4	−92.5 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄ClNO₅
M_r	381.84
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	173
a, b, c (Å)	11.7552 (9), 5.9139 (4), 13.8789 (11)
β (°)	109.023 (9)
V (Å³)	912.16 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.910, 0.954
No. of measured, independent and observed [I > 2s(I)] reflections	6562, 3594, 2515
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.047, 0.98
No. of reflections	3594
No. of parameters	237
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Absolute structure	Flack (1983), 1198 Friedel pairs
Absolute structure parameter	0.11 (5)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL-Plus (Sheldrick, 2008).

References

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