(11R)-13-(Benzyl­amino)-4,5-ep­oxy-11,13-dihydro­costunolide

The title compound, C₂₂H₂₉NO₃, was obtained by the reaction of benzyl­amine with parthenolide. X-ray crystal structure determination revealed that the configuration of the new chiral center at C11 is R, establishing the stereospecificity of the amination reaction.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.096
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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           68.01
           From the CIF: _reflns_number_total               3531
           Count of symmetry unique reflns         2050
           Completeness (_total/calc)            172.24%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1481
           Fraction of Friedel pairs measured     0.722
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

Parthenolide, is a germacrene sesquiterpene lactone. It has been isolated from several different species of plant in the Asteraceae (Compositae) family, feverfew (Tanacetum parthenium) being one of them (de Kraker et al., 2002). Its remarkable cytotoxic, antitumor, antiviral and antileishmanic properties have made it the focus of a large number of investigations. Its ability to induce tumor apoptosis through the inhibition of NF-kappaB make it a potential therapeutic for the treatment of leukemia (Guzman et al., 2005). Its development in this regard has been impeded by its low polarity and low water solubility. We saw a potential solution to this problem in the formation of a conjugate adduct of an amine species at the C-13, α-methylene group of the γ-butyrolactone function of parthenolide (Crooks et al., 2005). The title compound was synthesized as part of an ongoing drug discovery effort by reaction of benzylamine with parthenolide. The benzylamine adduct obtained was shown to be a single diastereomer by NMR analysis. The crystal structure of the title compound was determined to obtain the configuration of the newly formed stereocenter at C-11. An R absolute configuration was found. Bond distances and angles within the molecule are quite regular with average normal bonds (Allen et al., 1987). A hydrogen bond is observed between N-1H and O3 (2.30 (17) A°, 2.97 (17) A°, 130.2 (8) °) (Table 1) of the carbonyl oxygen of the 5-membered lactone ring, which can be considered as a weak hydrogen bond (Desiraju & Steiner, 1999).

Related literature

For related literature, see: Allen et al. (1987); Crooks et al. (2005); Desiraju & Steiner (1999); Guzman et al. (2005); de Kraker et al. (2002); Parsons & Flack (2004).

S2. Experimental

The title compound was prepared by dissolving parthenolide (100 mg, 0.403 mmol) in MeOH (10 ml) and adding benzylamine (43.1 mg, 0.403 mmol) to the solution. The mixture was stirred at room temperature for 18 h. The solvent was evaporated and the title compound was purified by column chromatography over silica gel by eluting with 15% acetone in hexane. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in chloroform/hexane at room temperature. The title compound was obtained as white crystals. ¹H NMR (CDCl₃, p.p.m.): δ 7.35–7.26 (m, 5H), 5.19 (app. d, 1H, J = 10.2), 3.92–3.75 (m, 3H), 3.02 (dd, 1H, J = 3.6 and 12.3 Hz), 2.74 (m, 2H), 2.44–1.78 (m, 11 H), 1.69 (s, 3H), 1.29 (s, 3H); ¹³C NMR (CDCl₃, δ, p.p.m.): 176.7, 140.0, 134.6, 128.5, 128.1, 127.1, 125.2, 82.7, 66.5, 61.7, 54.1, 48.4, 46.7, 46.2, 41.2, 36.8, 30.2, 24.3, 17.5, 17.2.

S3. Refinement

H atoms were found in difference Fourier maps and those attached to carbon atoms were subsequently placed in idealized positions with constrained C—H distances of 0.98Å (RCH₃), 0.99 Å (R₂CH₂), 1.00 Å (R₃CH) and 0.95 Å (C_ArH) with U_iso(H) values set to either 1.5U_eq(methyl) or 1.2U_eq of the attached C atom respectively. Since the NH hydrogen was clearly not planar, and there being no suitable riding model available, the coordinates of this H atom were refined but its U_iso was set to 1.5U_eq of the attached N atom.

Since this crystal structure was known to be of an all light-atom chiral compound, Cu Kα x-rays were used so that the absolute configuration could be determined from the anomalous scattering of the oxygen atoms. The value of the Flack parameter (Flack, 1983) based on refinement with unmerged Friedel pairs, as determined by the Parsons' quotient method (Parsons & Flack, 2004) was x(u) = 0.13 (6).

Computing details

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and local procedures.

Figures

	Fig. 1. A view of the asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level; H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A packing diagram, viewed down the a axis, hydrogen atoms have been omitted for clarity.

(11R)-13-(Benzylamino)-4,5-epoxy-11,13-dihydrocostunolide

Crystal data

C22H29NO3	F(000) = 768
Mr = 355.46	Dx = 1.208 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 7188 reflections
a = 8.3772 (6) Å	θ = 4.1–68.0°
b = 13.7441 (10) Å	µ = 0.63 mm^−1
c = 16.9684 (12) Å	T = 90 K
V = 1953.7 (2) Å^3	Rod, colourless
Z = 4	0.35 × 0.08 × 0.08 mm

Data collection

X8 Proteum diffractometer	3446 reflections with I > 2σ(I)
Radiation source: fine-focus rotating anode	Rint = 0.043
Helios multilayer optics monochromator	θmax = 68.0°, θmin = 4.1°
Detector resolution: 18 pixels mm^-1	h = −10→10
ω and φ scans	k = −16→16
21942 measured reflections	l = −20→20
3531 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0636P)^2 + 0.2363P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max = 0.001
S = 1.08	Δρmax = 0.26 e Å^−3
3531 reflections	Δρmin = −0.19 e Å^−3
241 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0055 (5)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 0000 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.13 (6)

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.

Flack parameter from normal least-squares (unmerged data): is x = 0.09232; su = 0.07777 Flack parameter from Parson's quotients: CC = 15.45, GooF 1.2789, Flack x = 0.1327; su = 0.0656 Result from Parsons quotients given in this CIF.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.48723 (15)	0.32099 (8)	0.46644 (9)	0.0325 (3)
H1N	0.422 (3)	0.3350 (9)	0.4245 (12)	0.049*
O1	0.24522 (12)	0.80545 (7)	0.50257 (5)	0.0269 (2)
O2	0.26117 (12)	0.60530 (7)	0.47005 (6)	0.0282 (2)
O3	0.28650 (15)	0.47566 (7)	0.39368 (6)	0.0397 (3)
C1	0.54615 (17)	0.79131 (10)	0.68316 (8)	0.0260 (3)
H1	0.6343	0.7856	0.6482	0.031*
C2	0.46528 (19)	0.88816 (10)	0.68533 (8)	0.0309 (3)
H2A	0.5454	0.9401	0.6938	0.037*
H2B	0.3883	0.8901	0.7296	0.037*
C3	0.37714 (17)	0.90558 (10)	0.60700 (8)	0.0292 (3)
H3A	0.3096	0.9644	0.6116	0.035*
H3B	0.4560	0.9170	0.5645	0.035*
C4	0.27459 (16)	0.81977 (10)	0.58600 (8)	0.0266 (3)
C5	0.35340 (15)	0.74075 (9)	0.54297 (7)	0.0211 (3)
H5	0.4688	0.7525	0.5313	0.025*
C6	0.30846 (16)	0.63576 (10)	0.54922 (7)	0.0233 (3)
H6	0.2174	0.6275	0.5868	0.028*
C7	0.44529 (16)	0.56754 (10)	0.57132 (8)	0.0247 (3)
H7	0.5462	0.5941	0.5484	0.030*
C8	0.4736 (2)	0.54673 (11)	0.65905 (9)	0.0349 (4)
H8A	0.3689	0.5472	0.6861	0.042*
H8B	0.5178	0.4802	0.6640	0.042*
C9	0.58504 (19)	0.61685 (10)	0.70247 (9)	0.0331 (3)
H9A	0.6238	0.5848	0.7511	0.040*
H9B	0.6789	0.6300	0.6687	0.040*
C10	0.50933 (17)	0.71205 (11)	0.72440 (8)	0.0305 (3)
C11	0.40039 (16)	0.47539 (10)	0.52589 (8)	0.0263 (3)
H11	0.3246	0.4365	0.5587	0.032*
C12	0.31212 (17)	0.51417 (10)	0.45586 (9)	0.0277 (3)
C13	0.53912 (17)	0.41115 (11)	0.50311 (10)	0.0335 (3)
H13A	0.6091	0.4469	0.4661	0.040*
H13B	0.6025	0.3958	0.5508	0.040*
C14	0.3954 (3)	0.70842 (16)	0.79204 (11)	0.0502 (5)
H14A	0.3438	0.7720	0.7981	0.075*
H14B	0.4536	0.6922	0.8404	0.075*
H14C	0.3141	0.6587	0.7820	0.075*
C15	0.13073 (18)	0.80289 (13)	0.63629 (10)	0.0369 (4)
H15A	0.0642	0.8615	0.6366	0.055*
H15B	0.1645	0.7878	0.6902	0.055*
H15C	0.0692	0.7482	0.6150	0.055*
C2'	0.62254 (18)	0.26381 (12)	0.44003 (13)	0.0444 (4)
H2'1	0.6892	0.2464	0.4861	0.053*
H2'2	0.6885	0.3036	0.4039	0.053*
C3'	0.57217 (17)	0.17232 (10)	0.39836 (10)	0.0329 (3)
C4'	0.62586 (19)	0.15239 (12)	0.32291 (10)	0.0389 (4)
H4'	0.6913	0.1983	0.2964	0.047*
C5'	0.58531 (19)	0.06646 (13)	0.28581 (9)	0.0391 (4)
H5'	0.6237	0.0532	0.2342	0.047*
C6'	0.48934 (19)	0.00007 (12)	0.32352 (9)	0.0351 (3)
H6'	0.4614	−0.0590	0.2980	0.042*
C7'	0.43343 (18)	0.01924 (11)	0.39868 (9)	0.0329 (3)
H7'	0.3664	−0.0264	0.4247	0.039*
C8'	0.47545 (17)	0.10493 (10)	0.43568 (9)	0.0307 (3)
H8'	0.4375	0.1178	0.4874	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0196 (6)	0.0285 (6)	0.0494 (7)	−0.0004 (5)	−0.0044 (6)	0.0005 (5)
O1	0.0237 (5)	0.0322 (5)	0.0248 (5)	0.0057 (4)	−0.0060 (4)	0.0004 (4)
O2	0.0274 (5)	0.0280 (5)	0.0291 (5)	0.0004 (4)	−0.0113 (4)	−0.0012 (4)
O3	0.0516 (7)	0.0332 (5)	0.0345 (6)	0.0028 (5)	−0.0147 (5)	−0.0036 (4)
C1	0.0213 (7)	0.0332 (7)	0.0236 (6)	−0.0046 (5)	−0.0039 (5)	−0.0001 (5)
C2	0.0319 (8)	0.0324 (7)	0.0284 (7)	−0.0029 (6)	−0.0016 (6)	−0.0044 (5)
C3	0.0296 (7)	0.0284 (6)	0.0296 (7)	0.0051 (6)	−0.0017 (6)	−0.0031 (6)
C4	0.0207 (6)	0.0351 (7)	0.0238 (6)	0.0069 (5)	−0.0025 (5)	−0.0024 (5)
C5	0.0148 (6)	0.0274 (6)	0.0213 (6)	0.0011 (5)	−0.0027 (5)	0.0007 (5)
C6	0.0182 (6)	0.0300 (6)	0.0215 (6)	−0.0040 (5)	−0.0026 (5)	−0.0002 (5)
C7	0.0209 (6)	0.0256 (6)	0.0276 (7)	−0.0063 (5)	−0.0060 (5)	0.0071 (5)
C8	0.0408 (9)	0.0327 (7)	0.0311 (7)	−0.0118 (7)	−0.0147 (7)	0.0110 (6)
C9	0.0313 (8)	0.0329 (7)	0.0350 (7)	−0.0068 (6)	−0.0134 (6)	0.0088 (6)
C10	0.0266 (7)	0.0373 (7)	0.0277 (7)	−0.0061 (6)	−0.0065 (6)	0.0044 (6)
C11	0.0204 (6)	0.0251 (6)	0.0334 (7)	−0.0053 (5)	−0.0055 (5)	0.0045 (6)
C12	0.0238 (6)	0.0261 (6)	0.0331 (7)	−0.0016 (6)	−0.0048 (6)	0.0006 (5)
C13	0.0196 (7)	0.0279 (7)	0.0531 (9)	−0.0040 (6)	−0.0065 (6)	0.0043 (6)
C14	0.0538 (11)	0.0618 (11)	0.0350 (8)	−0.0059 (9)	0.0059 (8)	0.0136 (8)
C15	0.0239 (7)	0.0512 (9)	0.0357 (8)	0.0058 (7)	0.0040 (6)	−0.0041 (6)
C2'	0.0202 (7)	0.0344 (8)	0.0784 (12)	0.0009 (6)	0.0010 (8)	−0.0026 (8)
C3'	0.0150 (6)	0.0324 (7)	0.0514 (9)	0.0046 (5)	0.0011 (6)	0.0049 (7)
C4'	0.0224 (7)	0.0471 (9)	0.0473 (9)	0.0084 (6)	0.0067 (6)	0.0191 (7)
C5'	0.0255 (7)	0.0611 (10)	0.0308 (7)	0.0157 (7)	0.0014 (6)	0.0070 (7)
C6'	0.0260 (7)	0.0422 (8)	0.0371 (7)	0.0095 (6)	−0.0029 (6)	−0.0046 (6)
C7'	0.0233 (7)	0.0362 (7)	0.0391 (8)	−0.0006 (6)	0.0007 (6)	0.0022 (6)
C8'	0.0194 (7)	0.0364 (7)	0.0361 (7)	0.0028 (6)	0.0043 (6)	−0.0005 (6)

Geometric parameters (Å, º)

N1—C2'	1.450 (2)	C9—C10	1.501 (2)
N1—C13	1.4532 (19)	C9—H9A	0.9900
N1—H1N	0.92 (2)	C9—H9B	0.9900
O1—C5	1.4429 (15)	C10—C14	1.494 (2)
O1—C4	1.4502 (16)	C11—C12	1.4975 (19)
O2—C12	1.3450 (17)	C11—C13	1.510 (2)
O2—C6	1.4617 (15)	C11—H11	1.0000
O3—C12	1.1998 (18)	C13—H13A	0.9900
C1—C10	1.331 (2)	C13—H13B	0.9900
C1—C2	1.494 (2)	C14—H14A	0.9800
C1—H1	0.9500	C14—H14B	0.9800
C2—C3	1.539 (2)	C14—H14C	0.9800
C2—H2A	0.9900	C15—H15A	0.9800
C2—H2B	0.9900	C15—H15B	0.9800
C3—C4	1.502 (2)	C15—H15C	0.9800
C3—H3A	0.9900	C2'—C3'	1.503 (2)
C3—H3B	0.9900	C2'—H2'1	0.9900
C4—C5	1.4658 (18)	C2'—H2'2	0.9900
C4—C15	1.495 (2)	C3'—C8'	1.384 (2)
C5—C6	1.4950 (18)	C3'—C4'	1.384 (2)
C5—H5	1.0000	C4'—C5'	1.381 (3)
C6—C7	1.5277 (19)	C4'—H4'	0.9500
C6—H6	1.0000	C5'—C6'	1.374 (2)
C7—C11	1.5297 (18)	C5'—H5'	0.9500
C7—C8	1.5343 (18)	C6'—C7'	1.384 (2)
C7—H7	1.0000	C6'—H6'	0.9500
C8—C9	1.531 (2)	C7'—C8'	1.380 (2)
C8—H8A	0.9900	C7'—H7'	0.9500
C8—H8B	0.9900	C8'—H8'	0.9500
C2'—N1—C13	111.13 (12)	H9A—C9—H9B	107.6
C2'—N1—H1N	109.8 (8)	C1—C10—C14	125.41 (16)
C13—N1—H1N	109.4 (8)	C1—C10—C9	119.03 (13)
C5—O1—C4	60.88 (8)	C14—C10—C9	115.56 (14)
C12—O2—C6	110.20 (10)	C12—C11—C13	112.65 (12)
C10—C1—C2	127.67 (14)	C12—C11—C7	103.10 (10)
C10—C1—H1	116.2	C13—C11—C7	115.08 (11)
C2—C1—H1	116.2	C12—C11—H11	108.6
C1—C2—C3	109.56 (11)	C13—C11—H11	108.6
C1—C2—H2A	109.8	C7—C11—H11	108.6
C3—C2—H2A	109.8	O3—C12—O2	120.76 (13)
C1—C2—H2B	109.8	O3—C12—C11	128.99 (13)
C3—C2—H2B	109.8	O2—C12—C11	110.25 (11)
H2A—C2—H2B	108.2	N1—C13—C11	112.21 (11)
C4—C3—C2	110.92 (11)	N1—C13—H13A	109.2
C4—C3—H3A	109.5	C11—C13—H13A	109.2
C2—C3—H3A	109.5	N1—C13—H13B	109.2
C4—C3—H3B	109.5	C11—C13—H13B	109.2
C2—C3—H3B	109.5	H13A—C13—H13B	107.9
H3A—C3—H3B	108.0	C10—C14—H14A	109.5
O1—C4—C5	59.32 (8)	C10—C14—H14B	109.5
O1—C4—C15	113.54 (12)	H14A—C14—H14B	109.5
C5—C4—C15	122.17 (13)	C10—C14—H14C	109.5
O1—C4—C3	115.80 (12)	H14A—C14—H14C	109.5
C5—C4—C3	116.26 (12)	H14B—C14—H14C	109.5
C15—C4—C3	116.59 (13)	C4—C15—H15A	109.5
O1—C5—C4	59.80 (8)	C4—C15—H15B	109.5
O1—C5—C6	118.06 (10)	H15A—C15—H15B	109.5
C4—C5—C6	124.50 (11)	C4—C15—H15C	109.5
O1—C5—H5	114.4	H15A—C15—H15C	109.5
C4—C5—H5	114.4	H15B—C15—H15C	109.5
C6—C5—H5	114.4	N1—C2'—C3'	112.29 (12)
O2—C6—C5	106.23 (10)	N1—C2'—H2'1	109.1
O2—C6—C7	104.67 (10)	C3'—C2'—H2'1	109.1
C5—C6—C7	114.89 (11)	N1—C2'—H2'2	109.1
O2—C6—H6	110.3	C3'—C2'—H2'2	109.1
C5—C6—H6	110.3	H2'1—C2'—H2'2	107.9
C7—C6—H6	110.3	C8'—C3'—C4'	118.74 (15)
C6—C7—C11	101.53 (10)	C8'—C3'—C2'	120.59 (15)
C6—C7—C8	117.94 (12)	C4'—C3'—C2'	120.63 (15)
C11—C7—C8	111.88 (11)	C5'—C4'—C3'	120.73 (15)
C6—C7—H7	108.3	C5'—C4'—H4'	119.6
C11—C7—H7	108.3	C3'—C4'—H4'	119.6
C8—C7—H7	108.3	C6'—C5'—C4'	119.98 (15)
C9—C8—C7	116.34 (12)	C6'—C5'—H5'	120.0
C9—C8—H8A	108.2	C4'—C5'—H5'	120.0
C7—C8—H8A	108.2	C5'—C6'—C7'	120.04 (15)
C9—C8—H8B	108.2	C5'—C6'—H6'	120.0
C7—C8—H8B	108.2	C7'—C6'—H6'	120.0
H8A—C8—H8B	107.4	C8'—C7'—C6'	119.70 (14)
C10—C9—C8	114.22 (13)	C8'—C7'—H7'	120.2
C10—C9—H9A	108.7	C6'—C7'—H7'	120.2
C8—C9—H9A	108.7	C7'—C8'—C3'	120.81 (14)
C10—C9—H9B	108.7	C7'—C8'—H8'	119.6
C8—C9—H9B	108.7	C3'—C8'—H8'	119.6
C10—C1—C2—C3	−110.86 (17)	C2—C1—C10—C9	168.37 (13)
C1—C2—C3—C4	50.01 (16)	C8—C9—C10—C1	−104.86 (16)
C5—O1—C4—C15	−114.63 (14)	C8—C9—C10—C14	74.63 (17)
C5—O1—C4—C3	106.53 (13)	C6—C7—C11—C12	29.69 (13)
C2—C3—C4—O1	−152.77 (11)	C8—C7—C11—C12	156.36 (12)
C2—C3—C4—C5	−85.95 (15)	C6—C7—C11—C13	152.74 (12)
C2—C3—C4—C15	69.67 (16)	C8—C7—C11—C13	−80.59 (16)
C4—O1—C5—C6	115.63 (13)	C6—O2—C12—O3	−179.43 (13)
C15—C4—C5—O1	100.10 (14)	C6—O2—C12—C11	−0.25 (15)
C3—C4—C5—O1	−105.76 (13)	C13—C11—C12—O3	35.0 (2)
O1—C4—C5—C6	−105.09 (13)	C7—C11—C12—O3	159.65 (16)
C15—C4—C5—C6	−5.0 (2)	C13—C11—C12—O2	−144.11 (12)
C3—C4—C5—C6	149.15 (12)	C7—C11—C12—O2	−19.44 (15)
C12—O2—C6—C5	141.96 (11)	C2'—N1—C13—C11	175.89 (14)
C12—O2—C6—C7	20.01 (14)	C12—C11—C13—N1	−67.32 (15)
O1—C5—C6—O2	48.47 (14)	C7—C11—C13—N1	174.88 (12)
C4—C5—C6—O2	119.49 (13)	C13—N1—C2'—C3'	−177.25 (14)
O1—C5—C6—C7	163.67 (11)	N1—C2'—C3'—C8'	−57.4 (2)
C4—C5—C6—C7	−125.31 (13)	N1—C2'—C3'—C4'	124.74 (16)
O2—C6—C7—C11	−30.40 (13)	C8'—C3'—C4'—C5'	−0.7 (2)
C5—C6—C7—C11	−146.50 (11)	C2'—C3'—C4'—C5'	177.20 (14)
O2—C6—C7—C8	−152.99 (11)	C3'—C4'—C5'—C6'	0.7 (2)
C5—C6—C7—C8	90.90 (14)	C4'—C5'—C6'—C7'	−0.1 (2)
C6—C7—C8—C9	−88.67 (17)	C5'—C6'—C7'—C8'	−0.5 (2)
C11—C7—C8—C9	154.15 (14)	C6'—C7'—C8'—C3'	0.4 (2)
C7—C8—C9—C10	78.04 (18)	C4'—C3'—C8'—C7'	0.2 (2)
C2—C1—C10—C14	−11.1 (2)	C2'—C3'—C8'—C7'	−177.73 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.92 (2)	2.30 (2)	2.9784 (17)	130 (1)