3-[2-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)eth­yl] 5-methyl 2,6-dimethyl-4-(3-nitro­phen­yl)-1,4-dihydro­pyridine-3,5-dicarboxyl­ate

The title compound, C₂₆H₂₃N₃O₈, is a nefidipine analogue. The dihydro­pyridine ring has a flattened boat conformation. No hydrogen bonds exist in the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.111
• Data-to-parameter ratio = 11.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT432_ALERT_2_C Short Inter X...Y Contact  O4     ..  C16     ..       2.92 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O7     ..  C9      ..       2.97 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O8     ..  C21     ..       3.01 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of C4     = ...          S

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

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

---

S1. Comment

4-Aryl-1,4-dihydropyridine-3,5-dicarboxylic diesters of the nefidipine type have become almost indispensable for the treatment of cardiovascular diseases since they first appeared on the market in 1975 (Yiu & Knaus, 1999; Goldmann & Stoltefuss, 1991). The compound, 2,6-dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine- 3,5-dicarboxylic acid 3-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl) -ethyl] ester 5-methyl ester, is a nefidipine analog. It can also be used as an intermediate for preparation of 2,6- dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-amino-ethyl) ester 5-methyl ester. Fig.1 shows the structure of the title compound. The dihydropyridine ring has a flattened boat conformation. This compares well with the structure of 3-(2-acetoxyethyl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine- 3,5-dicarboxylateand nefidipine (Sun et al., 2006; Hofmann & Cimiraglia, 1990; Ramusino & Varì, 1999). The atoms C4 and N1 are displaced from the mean planes formed by the other atoms in the same ring by 0.281 (1) Å and 0.125 (1) Å, respectively. The dihedral angle between the benzene ring and the C3/C2/C6/C5 plane is 88.02 (1)°.

Related literature

For related literature, see: Goldmann & Stoltefuss (1991); Hofmann & Cimiraglia (1990); Ramusino & Varì (1999); Sun et al. (2006); Yiu & Knaus (1999).

S2. Experimental

The title compound was prepared from 2,6-dimethyl-4- (m-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid mono-methyl ester and 2-(2–2ydroxy-ethyl)-isoindole-1,3-dione in CH₂Cl₂. 2,6-Dimethyl-4- (m-nitro-phenyl)-1,4-dihydro-pyridine- 3,5-dicarboxylic acid mono-methyl ester (332 mg, 1 mmol) and 2-methyl-propan-1-ol (191 mg, 1 mmol) were dissolved in 20 ml CH₂Cl₂, dicyclohexylcarbodiimide (206 mg,1 mmol) and added to the solution at 278 K. The reaction mixture was stirred at 276–279 K for a further 5 h. The solvent was removed by vacuum evaporation. The product was purified by chromatography on silica gel column (eluted by ethyl acetate and petroleum ether, 1:4) at room temperature. The product (455 mg) was obtained in a yield of 90%. Suitable crystals were obtained by slow evaporation of a solution in ethyl acetate and petroleum ether (1:4).

S3. Refinement

All H atoms were positioned geometrically and refined using a riding model, with C—H 0.97 Å, and U_iso(H) = 1.2U_eq(C) except for the H atom on N1 which was located in a Fourier map and freely refined.

Computing details

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

Fig. 1. A view of the title compound. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

3-[2-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl] 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Crystal data

C26H23N3O8	Dx = 1.474 Mg m^−3
Mr = 505.47	Melting point = 243–244 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.7713 (16) Å	Cell parameters from 2343 reflections
b = 16.372 (3) Å	θ = 2.3–22.5°
c = 17.945 (4) Å	µ = 0.11 mm^−1
β = 95.43 (3)°	T = 293 K
V = 2273.0 (8) Å^3	Block, yellow
Z = 4	0.10 × 0.08 × 0.04 mm
F(000) = 1056

Data collection

Rigaku Saturn diffractometer	4009 independent reflections
Radiation source: rotating anode	3635 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.035
Detector resolution: 7.31 pixels mm^-1	θmax = 25.0°, θmin = 1.7°
ω scans	h = −9→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→19
Tmin = 0.989, Tmax = 0.996	l = −16→21
13760 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.7911P] where P = (Fo^2 + 2Fc^2)/3
4009 reflections	(Δ/σ)max = 0.001
341 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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
O1	0.49383 (17)	0.38716 (8)	0.52148 (7)	0.0286 (3)
O2	0.21767 (16)	0.34959 (8)	0.49192 (7)	0.0249 (3)
O3	−0.22762 (16)	0.13687 (9)	0.55571 (8)	0.0320 (3)
O4	−0.15986 (17)	0.02564 (8)	0.61640 (8)	0.0305 (3)
O5	0.01803 (15)	0.14288 (7)	0.32204 (7)	0.0216 (3)
O6	0.19557 (14)	0.08248 (7)	0.24663 (7)	0.0201 (3)
O7	0.48119 (16)	−0.02815 (8)	0.13320 (7)	0.0243 (3)
O8	0.06068 (15)	−0.14941 (8)	0.25700 (8)	0.0277 (3)
N1	0.61576 (19)	0.19920 (9)	0.36933 (8)	0.0202 (3)
N2	−0.12398 (18)	0.08343 (9)	0.57705 (8)	0.0230 (3)
N3	0.23954 (17)	−0.07506 (9)	0.18687 (8)	0.0194 (3)
C1	0.7467 (2)	0.31005 (11)	0.44434 (10)	0.0221 (4)
H1A	0.7234	0.3671	0.4363	0.033*
H1B	0.8402	0.2937	0.4163	0.033*
H1C	0.7779	0.3004	0.4966	0.033*
C2	0.5881 (2)	0.26132 (10)	0.41896 (10)	0.0186 (4)
C3	0.4268 (2)	0.27317 (10)	0.43928 (9)	0.0182 (4)
C4	0.2811 (2)	0.21423 (10)	0.41495 (9)	0.0180 (4)
H4	0.1758	0.2463	0.4024	0.022*
C5	0.3193 (2)	0.16685 (10)	0.34544 (9)	0.0178 (4)
C6	0.4839 (2)	0.15767 (10)	0.32777 (10)	0.0188 (4)
C7	0.5472 (2)	0.10637 (11)	0.26678 (10)	0.0240 (4)
H7A	0.5237	0.0499	0.2760	0.036*
H7B	0.6694	0.1140	0.2658	0.036*
H7C	0.4889	0.1223	0.2195	0.036*
C8	0.3901 (2)	0.34176 (11)	0.48782 (10)	0.0200 (4)
C9	0.1646 (3)	0.41683 (12)	0.53670 (11)	0.0307 (5)
H9A	0.2016	0.4069	0.5885	0.046*
H9B	0.0410	0.4217	0.5304	0.046*
H9C	0.2159	0.4665	0.5210	0.046*
C10	0.2465 (2)	0.15458 (10)	0.47756 (9)	0.0177 (4)
C11	0.0819 (2)	0.14706 (10)	0.50058 (10)	0.0192 (4)
H11	−0.0075	0.1803	0.4802	0.023*
C12	0.0524 (2)	0.08944 (10)	0.55433 (9)	0.0190 (4)
C13	0.1800 (2)	0.03819 (11)	0.58675 (10)	0.0214 (4)
H13	0.1560	−0.0009	0.6219	0.026*
C14	0.3446 (2)	0.04740 (11)	0.56474 (10)	0.0234 (4)
H14	0.4343	0.0150	0.5862	0.028*
C15	0.3767 (2)	0.10468 (11)	0.51081 (10)	0.0214 (4)
H15	0.4882	0.1098	0.4965	0.026*
C16	0.1640 (2)	0.13082 (10)	0.30507 (9)	0.0178 (4)
C17	0.0471 (2)	0.03969 (11)	0.21084 (10)	0.0222 (4)
H17A	−0.0353	0.0782	0.1868	0.027*
H17B	−0.0098	0.0087	0.2475	0.027*
C18	0.1126 (2)	−0.01691 (11)	0.15341 (10)	0.0222 (4)
H18A	0.0159	−0.0466	0.1283	0.027*
H18B	0.1647	0.0152	0.1161	0.027*
C19	0.4159 (2)	−0.07257 (10)	0.17660 (10)	0.0186 (4)
C20	0.4994 (2)	−0.13393 (10)	0.22918 (9)	0.0184 (4)
C21	0.6719 (2)	−0.15324 (11)	0.24496 (10)	0.0210 (4)
H21	0.7568	−0.1284	0.2196	0.025*
C22	0.7138 (2)	−0.21128 (11)	0.30038 (10)	0.0233 (4)
H22	0.8288	−0.2256	0.3125	0.028*
C23	0.5864 (2)	−0.24808 (11)	0.33774 (10)	0.0243 (4)
H23	0.6180	−0.2868	0.3744	0.029*
C24	0.4130 (2)	−0.22880 (11)	0.32195 (10)	0.0221 (4)
H24	0.3279	−0.2537	0.3471	0.027*
C25	0.3725 (2)	−0.17085 (10)	0.26712 (10)	0.0184 (4)
C26	0.2036 (2)	−0.13412 (11)	0.23925 (10)	0.0199 (4)
H1	0.724 (3)	0.1938 (13)	0.3578 (12)	0.033 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0341 (7)	0.0245 (7)	0.0270 (7)	−0.0051 (6)	0.0015 (6)	−0.0079 (6)
O2	0.0263 (7)	0.0240 (7)	0.0240 (7)	0.0073 (5)	−0.0005 (5)	−0.0078 (5)
O3	0.0210 (7)	0.0389 (8)	0.0365 (8)	0.0058 (6)	0.0051 (6)	0.0092 (6)
O4	0.0312 (7)	0.0294 (8)	0.0316 (8)	−0.0078 (6)	0.0074 (6)	0.0046 (6)
O5	0.0185 (6)	0.0236 (7)	0.0225 (7)	0.0010 (5)	0.0012 (5)	−0.0010 (5)
O6	0.0184 (6)	0.0217 (7)	0.0198 (6)	−0.0013 (5)	−0.0012 (5)	−0.0047 (5)
O7	0.0299 (7)	0.0231 (7)	0.0203 (7)	−0.0034 (5)	0.0044 (5)	0.0018 (5)
O8	0.0160 (6)	0.0292 (7)	0.0385 (8)	−0.0026 (5)	0.0060 (6)	−0.0016 (6)
N1	0.0177 (8)	0.0205 (8)	0.0222 (8)	0.0002 (6)	0.0014 (6)	−0.0012 (6)
N2	0.0218 (8)	0.0253 (8)	0.0220 (8)	−0.0035 (7)	0.0028 (6)	−0.0005 (7)
N3	0.0183 (7)	0.0198 (8)	0.0198 (8)	0.0012 (6)	0.0003 (6)	−0.0015 (6)
C1	0.0204 (9)	0.0210 (9)	0.0242 (10)	−0.0019 (7)	−0.0010 (7)	0.0017 (8)
C2	0.0234 (9)	0.0168 (9)	0.0150 (8)	−0.0005 (7)	−0.0007 (7)	0.0024 (7)
C3	0.0227 (9)	0.0167 (9)	0.0147 (9)	0.0000 (7)	−0.0009 (7)	0.0016 (7)
C4	0.0182 (8)	0.0175 (9)	0.0180 (9)	0.0017 (7)	0.0007 (7)	−0.0021 (7)
C5	0.0202 (9)	0.0152 (8)	0.0175 (9)	−0.0002 (7)	−0.0008 (7)	−0.0003 (7)
C6	0.0212 (9)	0.0168 (9)	0.0182 (9)	0.0001 (7)	0.0001 (7)	0.0007 (7)
C7	0.0209 (9)	0.0276 (10)	0.0238 (10)	−0.0013 (8)	0.0034 (8)	−0.0063 (8)
C8	0.0249 (9)	0.0184 (9)	0.0163 (9)	0.0004 (7)	0.0011 (7)	0.0025 (7)
C9	0.0371 (11)	0.0297 (11)	0.0249 (10)	0.0143 (9)	0.0012 (9)	−0.0087 (8)
C10	0.0204 (9)	0.0170 (9)	0.0156 (9)	−0.0002 (7)	0.0005 (7)	−0.0049 (7)
C11	0.0201 (9)	0.0185 (9)	0.0188 (9)	0.0015 (7)	0.0004 (7)	−0.0037 (7)
C12	0.0182 (8)	0.0206 (9)	0.0185 (9)	−0.0012 (7)	0.0030 (7)	−0.0046 (7)
C13	0.0263 (9)	0.0184 (9)	0.0200 (9)	0.0019 (7)	0.0043 (8)	0.0007 (7)
C14	0.0231 (9)	0.0231 (10)	0.0237 (10)	0.0074 (7)	0.0002 (8)	0.0035 (8)
C15	0.0187 (9)	0.0241 (10)	0.0216 (9)	0.0016 (7)	0.0021 (7)	−0.0007 (7)
C16	0.0228 (9)	0.0159 (9)	0.0146 (9)	0.0008 (7)	0.0008 (7)	0.0015 (7)
C17	0.0176 (9)	0.0226 (9)	0.0251 (10)	0.0016 (7)	−0.0046 (7)	−0.0036 (8)
C18	0.0226 (9)	0.0216 (9)	0.0206 (9)	0.0040 (7)	−0.0069 (7)	−0.0031 (7)
C19	0.0208 (9)	0.0186 (9)	0.0165 (9)	−0.0027 (7)	0.0017 (7)	−0.0044 (7)
C20	0.0205 (9)	0.0184 (9)	0.0164 (9)	0.0001 (7)	0.0019 (7)	−0.0022 (7)
C21	0.0190 (9)	0.0226 (9)	0.0217 (9)	−0.0016 (7)	0.0034 (7)	−0.0020 (7)
C22	0.0199 (9)	0.0263 (10)	0.0229 (10)	0.0036 (7)	−0.0017 (7)	−0.0039 (8)
C23	0.0318 (10)	0.0204 (9)	0.0200 (10)	0.0048 (8)	−0.0013 (8)	0.0004 (7)
C24	0.0265 (9)	0.0191 (9)	0.0215 (9)	−0.0017 (7)	0.0064 (8)	0.0006 (7)
C25	0.0189 (9)	0.0168 (9)	0.0197 (9)	−0.0013 (7)	0.0036 (7)	−0.0034 (7)
C26	0.0189 (9)	0.0195 (9)	0.0213 (9)	−0.0012 (7)	0.0017 (7)	−0.0059 (7)

Geometric parameters (Å, º)

O1—C8	1.215 (2)	C7—H7C	0.9600
O2—C8	1.355 (2)	C9—H9A	0.9600
O2—C9	1.446 (2)	C9—H9B	0.9600
O3—N2	1.226 (2)	C9—H9C	0.9600
O4—N2	1.228 (2)	C10—C11	1.387 (2)
O5—C16	1.218 (2)	C10—C15	1.391 (2)
O6—C16	1.355 (2)	C11—C12	1.384 (2)
O6—C17	1.447 (2)	C11—H11	0.9300
O7—C19	1.211 (2)	C12—C13	1.385 (2)
O8—C26	1.210 (2)	C13—C14	1.382 (3)
N1—C2	1.382 (2)	C13—H13	0.9300
N1—C6	1.387 (2)	C14—C15	1.387 (3)
N1—H1	0.89 (2)	C14—H14	0.9300
N2—C12	1.470 (2)	C15—H15	0.9300
N3—C26	1.395 (2)	C17—C18	1.510 (2)
N3—C19	1.401 (2)	C17—H17A	0.9700
N3—C18	1.459 (2)	C17—H17B	0.9700
C1—C2	1.502 (2)	C18—H18A	0.9700
C1—H1A	0.9600	C18—H18B	0.9700
C1—H1B	0.9600	C19—C20	1.485 (2)
C1—H1C	0.9600	C20—C21	1.380 (2)
C2—C3	1.353 (2)	C20—C25	1.389 (2)
C3—C8	1.466 (2)	C21—C22	1.392 (3)
C3—C4	1.520 (2)	C21—H21	0.9300
C4—C5	1.522 (2)	C22—C23	1.385 (3)
C4—C10	1.532 (2)	C22—H22	0.9300
C4—H4	0.9800	C23—C24	1.387 (3)
C5—C6	1.355 (2)	C23—H23	0.9300
C5—C16	1.471 (2)	C24—C25	1.382 (3)
C6—C7	1.499 (2)	C24—H24	0.9300
C7—H7A	0.9600	C25—C26	1.487 (2)
C7—H7B	0.9600
C8—O2—C9	115.98 (14)	C12—C11—H11	120.4
C16—O6—C17	115.54 (13)	C10—C11—H11	120.4
C2—N1—C6	123.74 (15)	C11—C12—C13	123.15 (16)
C2—N1—H1	115.5 (14)	C11—C12—N2	117.34 (15)
C6—N1—H1	119.5 (14)	C13—C12—N2	119.51 (15)
O3—N2—O4	123.44 (15)	C14—C13—C12	117.33 (16)
O3—N2—C12	117.91 (14)	C14—C13—H13	121.3
O4—N2—C12	118.64 (15)	C12—C13—H13	121.3
C26—N3—C19	111.71 (14)	C13—C14—C15	120.40 (16)
C26—N3—C18	123.98 (14)	C13—C14—H14	119.8
C19—N3—C18	123.96 (14)	C15—C14—H14	119.8
C2—C1—H1A	109.5	C14—C15—C10	121.64 (16)
C2—C1—H1B	109.5	C14—C15—H15	119.2
H1A—C1—H1B	109.5	C10—C15—H15	119.2
C2—C1—H1C	109.5	O5—C16—O6	121.97 (15)
H1A—C1—H1C	109.5	O5—C16—C5	123.50 (15)
H1B—C1—H1C	109.5	O6—C16—C5	114.53 (14)
C3—C2—N1	118.93 (16)	O6—C17—C18	107.07 (14)
C3—C2—C1	126.66 (16)	O6—C17—H17A	110.3
N1—C2—C1	114.41 (15)	C18—C17—H17A	110.3
C2—C3—C8	120.51 (16)	O6—C17—H17B	110.3
C2—C3—C4	121.06 (15)	C18—C17—H17B	110.3
C8—C3—C4	118.39 (14)	H17A—C17—H17B	108.6
C3—C4—C5	111.17 (14)	N3—C18—C17	112.23 (14)
C3—C4—C10	111.82 (14)	N3—C18—H18A	109.2
C5—C4—C10	109.73 (14)	C17—C18—H18A	109.2
C3—C4—H4	108.0	N3—C18—H18B	109.2
C5—C4—H4	108.0	C17—C18—H18B	109.2
C10—C4—H4	108.0	H18A—C18—H18B	107.9
C6—C5—C16	126.09 (16)	O7—C19—N3	125.22 (16)
C6—C5—C4	120.68 (15)	O7—C19—C20	129.07 (16)
C16—C5—C4	113.16 (14)	N3—C19—C20	105.71 (14)
C5—C6—N1	119.05 (16)	C21—C20—C25	121.37 (17)
C5—C6—C7	127.96 (16)	C21—C20—C19	130.00 (16)
N1—C6—C7	112.99 (15)	C25—C20—C19	108.56 (15)
C6—C7—H7A	109.5	C20—C21—C22	117.36 (16)
C6—C7—H7B	109.5	C20—C21—H21	121.3
H7A—C7—H7B	109.5	C22—C21—H21	121.3
C6—C7—H7C	109.5	C23—C22—C21	120.92 (17)
H7A—C7—H7C	109.5	C23—C22—H22	119.5
H7B—C7—H7C	109.5	C21—C22—H22	119.5
O1—C8—O2	121.89 (16)	C22—C23—C24	121.82 (17)
O1—C8—C3	127.38 (16)	C22—C23—H23	119.1
O2—C8—C3	110.73 (15)	C24—C23—H23	119.1
O2—C9—H9A	109.5	C25—C24—C23	116.93 (16)
O2—C9—H9B	109.5	C25—C24—H24	121.5
H9A—C9—H9B	109.5	C23—C24—H24	121.5
O2—C9—H9C	109.5	C24—C25—C20	121.60 (16)
H9A—C9—H9C	109.5	C24—C25—C26	130.64 (16)
H9B—C9—H9C	109.5	C20—C25—C26	107.72 (15)
C11—C10—C15	118.33 (16)	O8—C26—N3	124.62 (16)
C11—C10—C4	120.40 (15)	O8—C26—C25	129.12 (17)
C15—C10—C4	121.23 (15)	N3—C26—C25	106.26 (14)
C12—C11—C10	119.11 (16)
C6—N1—C2—C3	12.7 (3)	C13—C14—C15—C10	0.3 (3)
C6—N1—C2—C1	−166.72 (15)	C11—C10—C15—C14	1.2 (3)
N1—C2—C3—C8	−175.91 (15)	C4—C10—C15—C14	−176.51 (16)
C1—C2—C3—C8	3.5 (3)	C17—O6—C16—O5	−6.1 (2)
N1—C2—C3—C4	6.4 (2)	C17—O6—C16—C5	173.91 (14)
C1—C2—C3—C4	−174.24 (16)	C6—C5—C16—O5	−177.82 (17)
C2—C3—C4—C5	−22.4 (2)	C4—C5—C16—O5	5.4 (2)
C8—C3—C4—C5	159.82 (14)	C6—C5—C16—O6	2.1 (2)
C2—C3—C4—C10	100.59 (18)	C4—C5—C16—O6	−174.63 (14)
C8—C3—C4—C10	−77.15 (19)	C16—O6—C17—C18	−174.08 (14)
C3—C4—C5—C6	22.5 (2)	C26—N3—C18—C17	63.0 (2)
C10—C4—C5—C6	−101.67 (18)	C19—N3—C18—C17	−109.65 (18)
C3—C4—C5—C16	−160.50 (14)	O6—C17—C18—N3	58.87 (19)
C10—C4—C5—C16	75.28 (17)	C26—N3—C19—O7	178.32 (16)
C16—C5—C6—N1	176.72 (15)	C18—N3—C19—O7	−8.2 (3)
C4—C5—C6—N1	−6.7 (2)	C26—N3—C19—C20	−1.94 (18)
C16—C5—C6—C7	−3.4 (3)	C18—N3—C19—C20	171.54 (15)
C4—C5—C6—C7	173.12 (16)	O7—C19—C20—C21	3.7 (3)
C2—N1—C6—C5	−12.5 (3)	N3—C19—C20—C21	−176.02 (17)
C2—N1—C6—C7	167.58 (16)	O7—C19—C20—C25	−179.33 (17)
C9—O2—C8—O1	2.0 (2)	N3—C19—C20—C25	0.94 (18)
C9—O2—C8—C3	−178.35 (14)	C25—C20—C21—C22	0.1 (3)
C2—C3—C8—O1	−9.6 (3)	C19—C20—C21—C22	176.70 (17)
C4—C3—C8—O1	168.13 (17)	C20—C21—C22—C23	0.2 (3)
C2—C3—C8—O2	170.75 (15)	C21—C22—C23—C24	−0.2 (3)
C4—C3—C8—O2	−11.5 (2)	C22—C23—C24—C25	−0.1 (3)
C3—C4—C10—C11	125.58 (17)	C23—C24—C25—C20	0.4 (3)
C5—C4—C10—C11	−110.58 (17)	C23—C24—C25—C26	−177.07 (17)
C3—C4—C10—C15	−56.8 (2)	C21—C20—C25—C24	−0.4 (3)
C5—C4—C10—C15	67.1 (2)	C19—C20—C25—C24	−177.65 (16)
C15—C10—C11—C12	−1.3 (2)	C21—C20—C25—C26	177.59 (16)
C4—C10—C11—C12	176.42 (15)	C19—C20—C25—C26	0.32 (19)
C10—C11—C12—C13	0.0 (3)	C19—N3—C26—O8	−178.54 (16)
C10—C11—C12—N2	−179.92 (15)	C18—N3—C26—O8	8.0 (3)
O3—N2—C12—C11	−10.4 (2)	C19—N3—C26—C25	2.14 (18)
O4—N2—C12—C11	169.81 (15)	C18—N3—C26—C25	−171.34 (14)
O3—N2—C12—C13	169.71 (16)	C24—C25—C26—O8	−3.0 (3)
O4—N2—C12—C13	−10.1 (2)	C20—C25—C26—O8	179.25 (18)
C11—C12—C13—C14	1.5 (3)	C24—C25—C26—N3	176.26 (17)
N2—C12—C13—C14	−178.62 (15)	C20—C25—C26—N3	−1.47 (18)
C12—C13—C14—C15	−1.6 (3)