(3R,3aS,6R,6aR)-tert-Butyl N-(6-chloro-2-oxo-6a-phenyl­perhydro­furo[3,2-b]furan-3-yl)carbamate

The chiral title compound, C₁₇H₂₀ClNO₅, arose as a side product during the synthesis of novel furan­omycin derivatives. The stereochemistry at the bicyclic core is consistent with a halolactonization step. The five-membered rings are nearly perpendicular to each other [torsion angle at the common bond: -88.3 (3)°].

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.029
• wR factor = 0.079
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         33 Perc.
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C14
PLAT331_ALERT_2_B Small Average Phenyl C-C Dist.   C1     -C6            1.36 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Cl     -   C8      ..       5.99 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N      -   C13     ..       5.84 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT420_ALERT_2_C D-H Without Acceptor       N      -   H0     ...          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.79
           From the CIF: _reflns_number_total               3280
           Count of symmetry unique reflns         1967
           Completeness (_total/calc)            166.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1313
           Fraction of Friedel pairs measured     0.668
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound, (I), is a side product in the preparation of novel furanomycin derivatives using the gold-catalyzed cyclization of α-hydroxyallenes (Hoffmann-Röder & Krause, 2001). It was obtained after an aldehyde oxidation in the presence of NaClO₂ and chlorolactonization of the resulted boc-protected amino acid intermediate by hypochloric acid, a degradation product of the oxidant (Erdsack & Krause, 2007). A crystal structure determination of (I) has now been carried out to establish the relative configuration of the stereogenic centers at the bicyclic core. Fig. 1 shows that the relative configuration of C6 and C6a is consistent with the stereospecific halolactonization step. The torsion angle O3—C7—C10—O1 is -88.3 (3)°. The configurations of the stereogenic C atoms in (I) (C3 R, C3a S, C6 R and C6a R) were established by refining the Flack (1983) absolute structure parameter; they are consistent with those of the equivalent atoms in the starting material (Erdsack et al., 2007).

Related literature

For related literature, see: Erdsack & Krause (2007); Erdsack et al. (2007); Flack (1983); Hoffmann-Röder & Krause (2001).

S2. Experimental

In a Schlenk tube equipped with a magnetic stirrer bar, 47 mg (0.15 mmol) of tert-butyl-(1R,2S)-[2-hydroxy-1-(3-phenyl-2,5-dihydrofuran-2-yl)-ethyl]-carbamate (synthesis of this compound will be described elsewhere; Erdsack & Krause 2007) was dissolved in dry dichloromethane (1.5 ml) under argon and cooled to 273 K. With stirring, 87 mg (0.23 mmol) of Dess-Martin periodinane was added in one portion. After 2 h, the mixture was diluted with diethyl ether (3 ml), quenched with sat. aq. NaHCO₃ and sat. aq. Na₂S₂O₃ 1:1 (5 ml) and diluted with additional 3 ml of diethyl ether. After a few minutes with stirring at r.t., the biphasic mixture came clear. The organic phase was separated and the residue was extracted with diethyl ether (3 × 10 ml). The combined organic layers were washed with aq. sat. NaHCO₃ and brine and dried with MgSO₄. The solution was filtered and the solvent was evaporated. The crude aldehyde was dissolved in a 1:1 mixture of t-BuOH/THF (5 ml). The flask was sealed with a rubber septum and was cooled to 273 K. With vigorous stirring, a solution of NaClO₂ (80%, technical grade, 52 mg, 0.46 mmol) and NaH₂PO₄*H₂O (82 mg, 0.46 mmol) in 1 ml water was slowly added dropwise via syringe over 30 min. The reaction mixture came yellow and was allowed to stir at r.t. overnight. The mixture was diluted with water (15 ml) and extracted with diethyl ether (3 × 15 ml). The combined organic layers were dried (MgSO₄), filtered and the solvent was evaporated. The residue was purified by column chromatography on silica gel (iso-hexane/EtOAc 4:1 v/v) to give 28 mg (53%) of the lactone (I) as a solid, which was suspended in a few drops of iso-hexane. Ethyl acetate was added dropwise until the compound was completely dissolved, and colourless needles of (I) were obtained by slow evaporation at ambient temperature; mp 432 K; [α]_D²¹ - 44.0 (c 1.40, CHCl₃); IR (KBr pellet), cm^-1: 3419 (m), 3323 (m), 3062 (w), 2979 (m), 2932 (m), 2885 (w), 1801 (s), 1712 (s), 1510 (m), 1451 (m), 1393 (m), 1368 (m), 1253 (m), 1163 (s), 1104 (m), 1062 (m), 942 (s), 865 (m), 751 (m), 734 (m), 699 (m), 665 (w), 577 (w), 514 (w); ¹H NMR (400 MHz, CDCl₃): δ (p.p.m.): 7.48 - 7.43 (m, 5 H), 5.22 (dd, J = 6.3, 13.6 Hz, 1 H), 4.69 (dd, J = 4.0, 8.6 Hz, 1 H), 4.62 (d, J = 3.4 Hz, 1 H), 4.51 (dd, J = 3.9, 10.5 Hz, 1 H), 4.32 (d, J = 10.5 Hz, 1 H), 1.46 (m, 9 H); ¹³C NMR (100.6 MHz, CDCl₃): δ (p.p.m.) 172.0, 155.2, 132.1, 129.8, 128.7, 127.0, 94.8, 81.0, 80.1, 76.9, 63.3, 54.1, 28.2 HRMS (ESI): m/z calculated for C₁₇H₂₁O₅N³⁵Cl: [M + H]⁺ = 354.11028, found 354.11002

S3. Refinement

The H atoms were placed in calculated positions, with C—H = 0.93–0.98 and N—H = 0.86 Å and were refined as riding, with U_iso(H) = 1.5U_eq; the methyl groups were allowed to rotate but not to tip.

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures

Fig. 1. : The molecular structure of (I) with displacement ellipsoids shown at the 30% probability level (arbitrary spheres for the H atoms).

(3R,3aS,6R,6aR)-tert-Butyl N-(6-chloro-2-oxo-6a-phenylperhydrofuro[3,2-b]furan-3-yl)carbamate

Crystal data

C17H20ClNO5	F(000) = 744
Mr = 353.79	Dx = 1.342 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14042 reflections
a = 6.1519 (7) Å	θ = 3.1–25.8°
b = 12.029 (2) Å	µ = 0.24 mm^−1
c = 23.655 (4) Å	T = 291 K
V = 1750.5 (5) Å^3	Needle, colourless
Z = 4	0.44 × 0.08 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer	1085 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.036
Graphite monochromator	θmax = 25.8°, θmin = 3.1°
Detector resolution: 19 vertical, 18 horizontal pixels mm^-1	h = −7→7
309 frames via ω–rotation (Δω=1%) and two times 120 s per frame (three sets at different κ–angles) scans	k = 0→14
14042 measured reflections	l = 0→28
3280 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	[1.0exp(7.10(sinθ/λ)^2)]/[σ^2(Fo^2)]
wR(F^2) = 0.079	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 0.10 e Å^−3
3280 reflections	Δρmin = −0.11 e Å^−3
221 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0215 (9)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1313 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.08 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.6643 (2)	0.59959 (10)	0.85442 (5)	0.1028 (4)
O1	0.5371 (4)	0.6930 (2)	0.97543 (10)	0.0741 (7)
O2	0.0232 (4)	0.5437 (2)	1.04297 (11)	0.0772 (8)
O3	0.1997 (4)	0.5179 (2)	0.96171 (11)	0.0702 (7)
O4	0.5678 (5)	0.4974 (2)	1.14730 (11)	0.0925 (9)
O5	0.5498 (4)	0.6773 (2)	1.17002 (11)	0.0832 (8)
N	0.4380 (4)	0.6243 (2)	1.08588 (12)	0.0678 (8)
H0	0.3938	0.6917	1.0822	0.102*
C1	0.4893 (6)	0.4053 (3)	0.92572 (15)	0.0687 (10)
C2	0.3421 (8)	0.3404 (4)	0.89794 (16)	0.0938 (14)
H2	0.2048	0.3681	0.8894	0.141*
C3	0.3975 (9)	0.2339 (4)	0.88258 (19)	0.1040 (17)
H3	0.2977	0.1897	0.8635	0.156*
C4	0.5945 (10)	0.1938 (4)	0.8950 (2)	0.1002 (16)
H4	0.6314	0.1219	0.8843	0.150*
C5	0.7399 (9)	0.2570 (4)	0.9230 (2)	0.1152 (18)
H5	0.8761	0.2281	0.9317	0.173*
C6	0.6885 (8)	0.3633 (4)	0.93866 (18)	0.0982 (14)
H6	0.7891	0.4066	0.9581	0.147*
C7	0.4274 (6)	0.5205 (3)	0.94081 (14)	0.0601 (10)
C8	0.4180 (6)	0.6041 (3)	0.89390 (14)	0.0701 (10)
H8	0.2905	0.5928	0.8697	0.105*
C9	0.4034 (6)	0.7103 (3)	0.92654 (15)	0.0781 (12)
H9A	0.4570	0.7721	0.9042	0.117*
H9B	0.2543	0.7254	0.9375	0.117*
C10	0.5502 (5)	0.5787 (3)	0.98781 (15)	0.0626 (10)
H10	0.7011	0.5530	0.9906	0.094*
C11	0.4212 (5)	0.5507 (3)	1.03969 (15)	0.0649 (10)
H11	0.4684	0.4772	1.0527	0.097*
C12	0.1912 (7)	0.5391 (3)	1.01752 (18)	0.0662 (10)
C13	0.5233 (6)	0.5907 (4)	1.13647 (18)	0.0727 (11)
C14	0.6347 (7)	0.6647 (4)	1.22849 (16)	0.0861 (13)
C15	0.8603 (6)	0.6207 (5)	1.22662 (17)	0.132 (2)
H15A	0.9223	0.6230	1.2638	0.199*
H15B	0.9462	0.6653	1.2015	0.199*
H15C	0.8581	0.5453	1.2133	0.199*
C16	0.6267 (10)	0.7804 (4)	1.24998 (17)	0.156 (3)
H16A	0.4821	0.8091	1.2458	0.234*
H16B	0.7263	0.8257	1.2289	0.234*
H16C	0.6667	0.7813	1.2892	0.234*
C17	0.4855 (7)	0.5924 (4)	1.26134 (17)	0.1118 (15)
H17A	0.3408	0.6221	1.2596	0.168*
H17B	0.5325	0.5896	1.3000	0.168*
H17C	0.4866	0.5188	1.2456	0.168*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1244 (9)	0.0872 (8)	0.0967 (8)	0.0053 (8)	0.0295 (7)	0.0076 (7)
O1	0.0901 (18)	0.0578 (18)	0.0744 (18)	−0.0033 (16)	−0.0172 (15)	0.0027 (13)
O2	0.0676 (17)	0.0769 (19)	0.0872 (19)	0.0014 (16)	−0.0038 (15)	0.0033 (15)
O3	0.0584 (16)	0.0840 (19)	0.0682 (17)	0.0018 (16)	−0.0079 (14)	−0.0048 (14)
O4	0.126 (2)	0.0707 (19)	0.0810 (19)	0.0217 (19)	−0.0200 (18)	0.0004 (17)
O5	0.112 (2)	0.0692 (19)	0.0681 (17)	−0.0006 (18)	−0.0191 (16)	0.0014 (15)
N	0.080 (2)	0.059 (2)	0.0639 (19)	0.0043 (18)	−0.0168 (17)	0.0010 (17)
C1	0.069 (3)	0.065 (3)	0.073 (3)	0.001 (3)	−0.002 (2)	0.000 (2)
C2	0.107 (4)	0.085 (3)	0.089 (3)	0.003 (3)	−0.019 (3)	−0.018 (3)
C3	0.130 (5)	0.085 (4)	0.096 (3)	−0.016 (3)	−0.008 (3)	−0.017 (3)
C4	0.143 (5)	0.059 (3)	0.099 (4)	0.003 (4)	0.015 (4)	0.003 (3)
C5	0.111 (5)	0.071 (4)	0.163 (5)	0.015 (3)	−0.013 (4)	0.013 (4)
C6	0.093 (3)	0.058 (3)	0.144 (4)	0.007 (3)	−0.016 (3)	−0.009 (3)
C7	0.054 (2)	0.056 (3)	0.070 (3)	0.003 (2)	−0.004 (2)	−0.001 (2)
C8	0.074 (2)	0.069 (3)	0.067 (2)	0.007 (3)	−0.004 (2)	0.004 (2)
C9	0.091 (3)	0.068 (3)	0.076 (3)	0.006 (2)	−0.016 (3)	0.004 (2)
C10	0.059 (2)	0.058 (3)	0.070 (2)	0.000 (2)	−0.004 (2)	−0.001 (2)
C11	0.064 (2)	0.061 (3)	0.070 (2)	−0.002 (2)	−0.016 (2)	−0.006 (2)
C12	0.062 (3)	0.057 (3)	0.079 (3)	0.000 (2)	−0.008 (3)	0.000 (2)
C13	0.068 (3)	0.075 (3)	0.075 (3)	0.001 (3)	−0.001 (2)	−0.002 (3)
C14	0.107 (4)	0.099 (4)	0.053 (3)	−0.004 (3)	−0.018 (3)	0.010 (2)
C15	0.085 (3)	0.220 (6)	0.092 (3)	0.000 (4)	−0.021 (3)	0.021 (4)
C16	0.279 (8)	0.100 (4)	0.088 (4)	−0.015 (5)	−0.055 (5)	−0.023 (3)
C17	0.112 (3)	0.146 (4)	0.078 (3)	0.005 (4)	0.009 (3)	0.010 (3)

Geometric parameters (Å, º)

Cl—C8	1.781 (3)	C6—H6	0.9300
O1—C10	1.409 (4)	C7—C8	1.499 (4)
O1—C9	1.434 (4)	C7—C10	1.516 (4)
O2—C12	1.197 (4)	C8—C9	1.496 (5)
O3—C12	1.346 (4)	C8—H8	0.9800
O3—C7	1.486 (4)	C9—H9A	0.9700
O4—C13	1.183 (4)	C9—H9B	0.9700
O5—C13	1.320 (4)	C10—C11	1.500 (4)
O5—C14	1.486 (4)	C10—H10	0.9800
N—C13	1.368 (4)	C11—C12	1.516 (5)
N—C11	1.410 (4)	C11—H11	0.9800
N—H0	0.8600	C14—C16	1.483 (5)
C1—C6	1.360 (5)	C14—C17	1.484 (5)
C1—C2	1.364 (5)	C14—C15	1.486 (5)
C1—C7	1.481 (5)	C15—H15A	0.9600
C2—C3	1.374 (6)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C3—C4	1.337 (6)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.347 (6)	C16—H16C	0.9600
C4—H4	0.9300	C17—H17A	0.9600
C5—C6	1.369 (5)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C10—O1—C9	110.0 (3)	O1—C10—C11	111.0 (3)
C12—O3—C7	111.0 (3)	O1—C10—C7	105.6 (3)
C13—O5—C14	121.5 (3)	C11—C10—C7	103.5 (3)
C13—N—C11	121.4 (3)	O1—C10—H10	112.1
C13—N—H0	119.3	C11—C10—H10	112.1
C11—N—H0	119.3	C7—C10—H10	112.1
C6—C1—C2	119.6 (4)	N—C11—C10	117.0 (3)
C6—C1—C7	121.6 (4)	N—C11—C12	113.2 (3)
C2—C1—C7	118.7 (4)	C10—C11—C12	103.4 (3)
C1—C2—C3	119.7 (5)	N—C11—H11	107.6
C1—C2—H2	120.1	C10—C11—H11	107.6
C3—C2—H2	120.1	C12—C11—H11	107.6
C4—C3—C2	120.2 (5)	O2—C12—O3	122.4 (3)
C4—C3—H3	119.9	O2—C12—C11	128.9 (4)
C2—C3—H3	119.9	O3—C12—C11	108.7 (4)
C3—C4—C5	120.4 (5)	O4—C13—O5	126.2 (4)
C3—C4—H4	119.8	O4—C13—N	123.9 (4)
C5—C4—H4	119.8	O5—C13—N	109.9 (4)
C4—C5—C6	120.4 (5)	C16—C14—C17	110.5 (4)
C4—C5—H5	119.8	C16—C14—O5	102.2 (3)
C6—C5—H5	119.8	C17—C14—O5	109.3 (3)
C1—C6—C5	119.6 (5)	C16—C14—C15	112.0 (4)
C1—C6—H6	120.2	C17—C14—C15	112.6 (4)
C5—C6—H6	120.2	O5—C14—C15	109.7 (3)
C1—C7—O3	107.6 (3)	C14—C15—H15A	109.5
C1—C7—C8	117.4 (3)	C14—C15—H15B	109.5
O3—C7—C8	102.9 (3)	H15A—C15—H15B	109.5
C1—C7—C10	118.7 (3)	C14—C15—H15C	109.5
O3—C7—C10	103.6 (3)	H15A—C15—H15C	109.5
C8—C7—C10	104.6 (3)	H15B—C15—H15C	109.5
C7—C8—C9	101.1 (3)	C14—C16—H16A	109.5
C7—C8—Cl	109.6 (3)	C14—C16—H16B	109.5
C9—C8—Cl	110.3 (3)	H16A—C16—H16B	109.5
C7—C8—H8	111.8	C14—C16—H16C	109.5
C9—C8—H8	111.8	H16A—C16—H16C	109.5
Cl—C8—H8	111.8	H16B—C16—H16C	109.5
O1—C9—C8	105.0 (3)	C14—C17—H17A	109.5
O1—C9—H9A	110.8	C14—C17—H17B	109.5
C8—C9—H9A	110.8	H17A—C17—H17B	109.5
O1—C9—H9B	110.8	C14—C17—H17C	109.5
C8—C9—H9B	110.8	H17A—C17—H17C	109.5
H9A—C9—H9B	108.8	H17B—C17—H17C	109.5
C6—C1—C2—C3	−0.9 (6)	C9—O1—C10—C7	3.9 (4)
C7—C1—C2—C3	178.8 (4)	C1—C7—C10—O1	152.5 (3)
C1—C2—C3—C4	0.3 (7)	O3—C7—C10—O1	−88.3 (3)
C2—C3—C4—C5	0.4 (8)	C8—C7—C10—O1	19.3 (4)
C3—C4—C5—C6	−0.5 (8)	C1—C7—C10—C11	−90.8 (4)
C2—C1—C6—C5	0.9 (7)	O3—C7—C10—C11	28.5 (3)
C7—C1—C6—C5	−178.8 (4)	C8—C7—C10—C11	136.0 (3)
C4—C5—C6—C1	−0.2 (8)	C13—N—C11—C10	−116.8 (4)
C6—C1—C7—O3	−138.5 (4)	C13—N—C11—C12	123.1 (4)
C2—C1—C7—O3	41.8 (4)	O1—C10—C11—N	−42.8 (4)
C6—C1—C7—C8	106.1 (5)	C7—C10—C11—N	−155.7 (3)
C2—C1—C7—C8	−73.6 (5)	O1—C10—C11—C12	82.5 (4)
C6—C1—C7—C10	−21.4 (5)	C7—C10—C11—C12	−30.4 (4)
C2—C1—C7—C10	158.9 (4)	C7—O3—C12—O2	178.3 (3)
C12—O3—C7—C1	110.8 (3)	C7—O3—C12—C11	−3.7 (4)
C12—O3—C7—C8	−124.7 (3)	N—C11—C12—O2	−32.6 (6)
C12—O3—C7—C10	−15.9 (4)	C10—C11—C12—O2	−160.2 (4)
C1—C7—C8—C9	−167.4 (3)	N—C11—C12—O3	149.5 (3)
O3—C7—C8—C9	74.6 (3)	C10—C11—C12—O3	21.9 (4)
C10—C7—C8—C9	−33.4 (4)	C14—O5—C13—O4	−2.5 (7)
C1—C7—C8—Cl	−50.9 (4)	C14—O5—C13—N	178.3 (3)
O3—C7—C8—Cl	−168.9 (2)	C11—N—C13—O4	−7.9 (6)
C10—C7—C8—Cl	83.1 (3)	C11—N—C13—O5	171.3 (3)
C10—O1—C9—C8	−25.6 (4)	C13—O5—C14—C16	−177.6 (4)
C7—C8—C9—O1	36.0 (4)	C13—O5—C14—C17	−60.5 (5)
Cl—C8—C9—O1	−79.9 (3)	C13—O5—C14—C15	63.4 (5)
C9—O1—C10—C11	−107.7 (3)