Lappaconitine

Wang, Y.-P.; Sun, W.-X.; Zhang, J.; Liu, H.-S.; Wen, H.-H.

doi:10.1107/S1600536807007131

Lappaconitine

Y.-P. Wang, W.-X. Sun, J. Zhang, H.-S. Liu and H.-H. Wen

In the crystal structure of lappaconitine [systematic name: (1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17R)-20-ethyl-4,8,9-trihydroxy-1,14,16-trimethoxyacontin-4-yl 2-(acetylamino)benzoate], C₃₂H₄₄N₂O₈, the rings adopt chair, boat and envelope conformations. The absolute configuration of the title compound was assigned by reference to the reported hydrobromide salt.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007131/ww2045sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007131/ww2045Isup2.hkl Contains datablock I

CCDC reference: 604701

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.004 Å
R factor = 0.041
wR factor = 0.099
Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density ....       4.82

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.689
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.69 e/A   
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.06 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.89 Ratio

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           26.49
           From the CIF: _reflns_number_total               3600
           Count of symmetry unique reflns         3599
           Completeness (_total/calc)            100.03%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         1
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17    = .          R

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

  13 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(1S,4S,5S,7S,8S,9S,10S,11S,13R,14S,16S,17R)-20-ethyl-4,8,9-trihydroxy- 1,14,16-trimethoxyacontin-4-yl 2-(acetylamino)benzoate top

Crystal data top

C₃₂H₄₄N₂O₈	D_x = 1.297 Mg m⁻³
M_r = 584.69	Melting point: 224 K
Trigonal, P3₁21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 31 2"	Cell parameters from 7233 reflections
a = 10.8279 (4) Å	θ = 2.2–21.7°
c = 44.2504 (8) Å	µ = 0.09 mm⁻¹
V = 4493.0 (2) Å³	T = 294 K
Z = 6	Block, colourless
F(000) = 1884	0.50 × 0.47 × 0.40 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3107 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 26.5°, θ_min = 2.2°
φ and ω scans	h = −13→13
26234 measured reflections	k = −8→13
3600 independent reflections	l = −52→55

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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0392P)² + 1.8542P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.008
3600 reflections	Δρ_max = 0.69 e Å⁻³
387 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (4)

Special details top

Experimental. Spectroscopic analysis: ¹H NMR (CDCl₃, δ, p.p.m., selected signal): 1.10 (t, 3H), 3.26 (s, 6H), 3.36 (s, 3H), 6.98 (t, 1H), 7.46 (t, 1H), 7.90 (d, 1H), 8.64(d, 1H); ¹³C NMR (CDCl₃, δ, p.p.m.): 169.0, 167.3, 141.6, 134.3, 131.0, 122.3, 120.2, 115.7, 90.1, 84.6, 84.1, 82.8, 78.5, 75.6, 61.5, 57.9, 56.5, 56.1, 55.4, 50.9, 49.8, 48.9, 48.5, 47.5, 44.8, 36.2, 31.8, 26.7, 26.2, 25.5, 24.1, 13.5. Analysis, calculated for C₃₂H₄₄N₂O₈: C 65.72, H 7.59, N 4.79%; found: C 65.99, H 7.56, N 4.58%.

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	0.4155 (3)	0.7126 (3)	0.88688 (6)	0.0384 (6)
H1	0.3143	0.6826	0.8848	0.046*
C2	0.4973 (3)	0.8403 (3)	0.86626 (6)	0.0432 (7)
H2A	0.5970	0.8905	0.8722	0.052*
H2B	0.4607	0.9051	0.8687	0.052*
C3	0.4858 (3)	0.7977 (3)	0.83321 (6)	0.0450 (7)
H3A	0.3885	0.7591	0.8263	0.054*
H3B	0.5471	0.8804	0.8210	0.054*
C4	0.5307 (3)	0.6865 (3)	0.83017 (5)	0.0360 (6)
C5	0.4243 (3)	0.5477 (3)	0.84610 (5)	0.0351 (6)
H5	0.3276	0.5096	0.8381	0.042*
C6	0.4763 (3)	0.4392 (3)	0.84289 (5)	0.0394 (6)
H6A	0.5446	0.4659	0.8265	0.047*
H6B	0.3970	0.3443	0.8390	0.047*
C7	0.5473 (3)	0.4446 (3)	0.87365 (5)	0.0338 (6)
H7	0.6383	0.4474	0.8705	0.041*
C8	0.4493 (3)	0.3180 (3)	0.89370 (6)	0.0359 (6)
C9	0.2989 (3)	0.3040 (3)	0.89579 (5)	0.0355 (6)
C10	0.3089 (3)	0.4504 (3)	0.89867 (5)	0.0339 (6)
H10	0.2182	0.4385	0.8913	0.041*
C11	0.4302 (3)	0.5787 (3)	0.88074 (5)	0.0318 (6)
C12	0.3107 (3)	0.4715 (3)	0.93392 (6)	0.0432 (7)
H12A	0.3953	0.5592	0.9399	0.052*
H12B	0.2273	0.4761	0.9402	0.052*
C13	0.3103 (3)	0.3424 (3)	0.94844 (6)	0.0394 (6)
H13	0.2595	0.3183	0.9678	0.047*
C14	0.2273 (3)	0.2281 (3)	0.92513 (6)	0.0426 (7)
H14	0.1279	0.2064	0.9251	0.051*
C15	0.5182 (3)	0.3271 (3)	0.92501 (6)	0.0409 (7)
H15A	0.5084	0.2347	0.9292	0.049*
H15B	0.6194	0.3947	0.9233	0.049*
C16	0.4620 (3)	0.3698 (3)	0.95263 (5)	0.0411 (6)
H16	0.5253	0.4717	0.9565	0.049*
C17	0.5732 (3)	0.5878 (3)	0.88748 (5)	0.0311 (5)
H17	0.5868	0.5877	0.9094	0.037*
C18	0.6833 (3)	0.7360 (3)	0.84106 (5)	0.0382 (6)
H18A	0.7197	0.6828	0.8303	0.046*
H18B	0.7437	0.8360	0.8361	0.046*
C19	0.7826 (4)	0.9902 (4)	0.69914 (6)	0.0512 (8)
C20	0.8836 (4)	1.1390 (4)	0.70960 (7)	0.0667 (10)
H20A	0.9795	1.1634	0.7047	0.100*
H20B	0.8750	1.1448	0.7311	0.100*
H20C	0.8610	1.2043	0.6998	0.100*
C21	0.5997 (3)	0.7338 (3)	0.77651 (6)	0.0414 (7)
C22	0.3952 (6)	0.8379 (5)	0.92929 (9)	0.0957 (16)
H22A	0.4449	0.9332	0.9214	0.144*
H22B	0.4035	0.8411	0.9509	0.144*
H22C	0.2963	0.7932	0.9238	0.144*
C23	0.1593 (4)	0.0152 (4)	0.95286 (8)	0.0691 (10)
H23A	0.2134	0.0612	0.9707	0.104*
H23B	0.1497	−0.0775	0.9510	0.104*
H23C	0.0665	0.0057	0.9544	0.104*
C24	0.6019 (4)	0.3355 (5)	0.98873 (8)	0.0822 (13)
H24A	0.6508	0.3111	0.9739	0.123*
H24B	0.5971	0.2883	1.0074	0.123*
H24C	0.6526	0.4368	0.9918	0.123*
C25	0.8305 (3)	0.7331 (3)	0.88187 (6)	0.0418 (7)
H25A	0.8441	0.6645	0.8704	0.050*
H25B	0.8304	0.7115	0.9031	0.050*
C26	0.9540 (3)	0.8809 (4)	0.87572 (8)	0.0595 (9)
H26A	0.9667	0.8959	0.8543	0.089*
H26B	1.0392	0.8901	0.8845	0.089*
H26C	0.9344	0.9505	0.8844	0.089*
C1'	0.5646 (3)	0.6655 (3)	0.74604 (6)	0.0400 (6)
C2'	0.6298 (3)	0.7442 (3)	0.71956 (6)	0.0412 (7)
C3'	0.5976 (4)	0.6730 (4)	0.69187 (6)	0.0531 (8)
H3'	0.6416	0.7230	0.6743	0.064*
C4'	0.5018 (4)	0.5299 (4)	0.69038 (7)	0.0587 (9)
H4'	0.4812	0.4843	0.6717	0.070*
C5'	0.4348 (4)	0.4517 (4)	0.71597 (7)	0.0577 (8)
H5'	0.3688	0.3549	0.7146	0.069*
C6'	0.4680 (3)	0.5203 (3)	0.74357 (6)	0.0482 (7)
H6'	0.4247	0.4681	0.7609	0.058*
N1	0.7249 (3)	0.8911 (3)	0.72174 (5)	0.0469 (6)
H1A	0.7506	0.9235	0.7398	0.056*
N2	0.6922 (2)	0.7168 (2)	0.87405 (4)	0.0332 (5)
O1	0.7567 (3)	0.9629 (3)	0.67265 (5)	0.0817 (9)
O2	0.6909 (2)	0.8559 (2)	0.78145 (4)	0.0541 (6)
O3	0.5170 (2)	0.6422 (2)	0.79807 (4)	0.0436 (5)
O4	0.2112 (2)	0.2303 (2)	0.87038 (4)	0.0506 (5)
H4	0.2199	0.1612	0.8663	0.076*
O5	0.4340 (3)	0.1928 (2)	0.87853 (4)	0.0496 (5)
H5A	0.3864	0.1223	0.8891	0.074*
O6	0.2307 (2)	0.0982 (2)	0.92714 (4)	0.0484 (5)
O7	0.4625 (2)	0.2919 (3)	0.97851 (4)	0.0574 (6)
O8	0.4547 (3)	0.7594 (2)	0.91738 (4)	0.0539 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0394 (16)	0.0385 (15)	0.0376 (14)	0.0197 (13)	−0.0020 (12)	−0.0011 (12)
C2	0.0501 (17)	0.0348 (15)	0.0447 (15)	0.0212 (14)	0.0018 (13)	0.0025 (12)
C3	0.0505 (18)	0.0391 (16)	0.0424 (15)	0.0202 (15)	−0.0026 (13)	0.0084 (12)
C4	0.0407 (15)	0.0336 (14)	0.0268 (12)	0.0133 (12)	−0.0009 (11)	0.0035 (11)
C5	0.0344 (14)	0.0328 (14)	0.0306 (12)	0.0112 (12)	−0.0021 (11)	0.0024 (10)
C6	0.0470 (17)	0.0325 (14)	0.0314 (13)	0.0143 (13)	0.0059 (12)	0.0024 (11)
C7	0.0368 (14)	0.0327 (14)	0.0321 (12)	0.0175 (12)	0.0072 (11)	0.0021 (11)
C8	0.0410 (15)	0.0304 (14)	0.0350 (13)	0.0169 (12)	0.0056 (12)	0.0012 (11)
C9	0.0337 (14)	0.0334 (14)	0.0327 (13)	0.0117 (12)	0.0006 (11)	0.0036 (11)
C10	0.0272 (13)	0.0356 (14)	0.0356 (12)	0.0132 (11)	0.0012 (11)	0.0040 (11)
C11	0.0334 (14)	0.0305 (13)	0.0277 (11)	0.0132 (11)	0.0012 (10)	0.0016 (10)
C12	0.0467 (17)	0.0507 (18)	0.0362 (14)	0.0274 (15)	0.0115 (12)	0.0078 (12)
C13	0.0377 (15)	0.0460 (17)	0.0334 (13)	0.0202 (13)	0.0103 (11)	0.0095 (12)
C14	0.0350 (15)	0.0415 (16)	0.0447 (15)	0.0142 (13)	0.0069 (12)	0.0127 (13)
C15	0.0393 (16)	0.0445 (16)	0.0405 (14)	0.0222 (13)	0.0044 (12)	0.0099 (12)
C16	0.0393 (15)	0.0441 (16)	0.0341 (13)	0.0167 (13)	0.0016 (12)	0.0045 (12)
C17	0.0317 (13)	0.0299 (13)	0.0277 (11)	0.0123 (11)	0.0025 (10)	0.0005 (10)
C18	0.0377 (15)	0.0376 (15)	0.0313 (12)	0.0129 (13)	0.0031 (11)	0.0045 (11)
C19	0.068 (2)	0.064 (2)	0.0378 (15)	0.0451 (19)	0.0106 (15)	0.0111 (14)
C20	0.083 (3)	0.056 (2)	0.060 (2)	0.035 (2)	0.0161 (19)	0.0144 (17)
C21	0.0467 (17)	0.0427 (17)	0.0311 (13)	0.0195 (14)	0.0010 (12)	0.0067 (12)
C22	0.151 (5)	0.088 (3)	0.073 (2)	0.079 (3)	0.021 (3)	−0.017 (2)
C23	0.070 (2)	0.056 (2)	0.071 (2)	0.024 (2)	0.0177 (19)	0.0315 (18)
C24	0.068 (3)	0.126 (4)	0.060 (2)	0.054 (3)	−0.0140 (19)	0.011 (2)
C25	0.0344 (15)	0.0439 (17)	0.0407 (15)	0.0147 (13)	−0.0010 (12)	−0.0005 (13)
C26	0.0366 (17)	0.054 (2)	0.067 (2)	0.0064 (16)	−0.0038 (15)	0.0028 (16)
C1'	0.0411 (16)	0.0455 (16)	0.0332 (13)	0.0216 (13)	−0.0022 (12)	0.0008 (12)
C2'	0.0424 (16)	0.0554 (18)	0.0319 (13)	0.0290 (15)	−0.0004 (11)	0.0033 (13)
C3'	0.060 (2)	0.069 (2)	0.0352 (14)	0.0361 (19)	0.0023 (14)	−0.0025 (15)
C4'	0.072 (2)	0.072 (2)	0.0393 (16)	0.041 (2)	−0.0084 (15)	−0.0147 (16)
C5'	0.059 (2)	0.053 (2)	0.0558 (18)	0.0233 (17)	−0.0102 (16)	−0.0165 (16)
C6'	0.0512 (19)	0.0464 (18)	0.0442 (15)	0.0222 (16)	−0.0022 (13)	−0.0021 (13)
N1	0.0545 (16)	0.0521 (16)	0.0310 (11)	0.0244 (14)	0.0018 (11)	0.0047 (11)
N2	0.0304 (11)	0.0326 (12)	0.0310 (10)	0.0115 (10)	0.0005 (9)	0.0016 (9)
O1	0.134 (3)	0.0785 (18)	0.0354 (11)	0.0550 (19)	0.0027 (14)	0.0103 (11)
O2	0.0623 (14)	0.0415 (12)	0.0353 (10)	0.0087 (11)	0.0024 (10)	0.0024 (9)
O3	0.0526 (12)	0.0381 (10)	0.0275 (9)	0.0134 (10)	0.0004 (8)	0.0034 (8)
O4	0.0490 (12)	0.0406 (12)	0.0454 (11)	0.0098 (10)	−0.0091 (10)	−0.0015 (9)
O5	0.0634 (15)	0.0318 (11)	0.0505 (11)	0.0215 (11)	0.0150 (10)	0.0036 (9)
O6	0.0513 (13)	0.0361 (11)	0.0494 (11)	0.0156 (10)	0.0080 (10)	0.0136 (9)
O7	0.0553 (14)	0.0825 (17)	0.0367 (10)	0.0361 (13)	0.0019 (9)	0.0165 (11)
O8	0.0817 (17)	0.0462 (12)	0.0375 (10)	0.0348 (12)	−0.0004 (10)	−0.0051 (9)

Geometric parameters (Å, º) top

C1—O8	1.429 (3)	C17—H17	0.9800
C1—C2	1.517 (4)	C18—N2	1.484 (3)
C1—C11	1.559 (4)	C18—H18A	0.9700
C1—H1	0.9800	C18—H18B	0.9700
C2—C3	1.520 (4)	C19—O1	1.207 (3)
C2—H2A	0.9700	C19—N1	1.368 (4)
C2—H2B	0.9700	C19—C20	1.498 (5)
C3—C4	1.512 (4)	C20—H20A	0.9600
C3—H3A	0.9700	C20—H20B	0.9600
C3—H3B	0.9700	C20—H20C	0.9600
C4—O3	1.483 (3)	C21—O2	1.211 (4)
C4—C5	1.533 (4)	C21—O3	1.345 (3)
C4—C18	1.538 (4)	C21—C1'	1.493 (4)
C5—C6	1.543 (4)	C22—O8	1.401 (4)
C5—C11	1.563 (3)	C22—H22A	0.9600
C5—H5	0.9800	C22—H22B	0.9600
C6—C7	1.550 (4)	C22—H22C	0.9600
C6—H6A	0.9700	C23—O6	1.417 (3)
C6—H6B	0.9700	C23—H23A	0.9600
C7—C8	1.529 (4)	C23—H23B	0.9600
C7—C17	1.557 (4)	C23—H23C	0.9600
C7—H7	0.9800	C24—O7	1.412 (4)
C8—O5	1.446 (3)	C24—H24A	0.9600
C8—C15	1.553 (4)	C24—H24B	0.9600
C8—C9	1.561 (4)	C24—H24C	0.9600
C9—O4	1.430 (3)	C25—N2	1.459 (4)
C9—C14	1.524 (3)	C25—C26	1.511 (4)
C9—C10	1.539 (4)	C25—H25A	0.9700
C10—C11	1.569 (3)	C25—H25B	0.9700
C10—C12	1.575 (3)	C26—H26A	0.9600
C10—H10	0.9800	C26—H26B	0.9600
C11—C17	1.531 (4)	C26—H26C	0.9600
C12—C13	1.537 (4)	C1'—C6'	1.390 (4)
C12—H12A	0.9700	C1'—C2'	1.413 (4)
C12—H12B	0.9700	C2'—C3'	1.396 (4)
C13—C14	1.514 (4)	C2'—N1	1.401 (4)
C13—C16	1.527 (4)	C3'—C4'	1.369 (5)
C13—H13	0.9800	C3'—H3'	0.9300
C14—O6	1.428 (3)	C4'—C5'	1.382 (5)
C14—H14	0.9800	C4'—H4'	0.9300
C15—C16	1.536 (4)	C5'—C6'	1.380 (4)
C15—H15A	0.9700	C5'—H5'	0.9300
C15—H15B	0.9700	C6'—H6'	0.9300
C16—O7	1.425 (3)	N1—H1A	0.8600
C16—H16	0.9800	O4—H4	0.8200
C17—N2	1.471 (3)	O5—H5A	0.8200

O8—C1—C2	108.1 (2)	O7—C16—C13	107.7 (2)
O8—C1—C11	110.1 (2)	O7—C16—C15	110.0 (2)
C2—C1—C11	117.3 (2)	C13—C16—C15	113.2 (2)
O8—C1—H1	107.0	O7—C16—H16	108.6
C2—C1—H1	107.0	C13—C16—H16	108.6
C11—C1—H1	107.0	C15—C16—H16	108.6
C1—C2—C3	112.3 (2)	N2—C17—C11	111.1 (2)
C1—C2—H2A	109.1	N2—C17—C7	115.0 (2)
C3—C2—H2A	109.1	C11—C17—C7	100.8 (2)
C1—C2—H2B	109.1	N2—C17—H17	109.9
C3—C2—H2B	109.1	C11—C17—H17	109.9
H2A—C2—H2B	107.9	C7—C17—H17	109.9
C4—C3—C2	108.5 (2)	N2—C18—C4	113.1 (2)
C4—C3—H3A	110.0	N2—C18—H18A	109.0
C2—C3—H3A	110.0	C4—C18—H18A	109.0
C4—C3—H3B	110.0	N2—C18—H18B	109.0
C2—C3—H3B	110.0	C4—C18—H18B	109.0
H3A—C3—H3B	108.4	H18A—C18—H18B	107.8
O3—C4—C3	108.8 (2)	O1—C19—N1	124.0 (3)
O3—C4—C5	102.6 (2)	O1—C19—C20	121.3 (3)
C3—C4—C5	110.9 (2)	N1—C19—C20	114.8 (3)
O3—C4—C18	109.2 (2)	C19—C20—H20A	109.5
C3—C4—C18	114.3 (2)	C19—C20—H20B	109.5
C5—C4—C18	110.3 (2)	H20A—C20—H20B	109.5
C4—C5—C6	108.8 (2)	C19—C20—H20C	109.5
C4—C5—C11	108.1 (2)	H20A—C20—H20C	109.5
C6—C5—C11	105.2 (2)	H20B—C20—H20C	109.5
C4—C5—H5	111.5	O2—C21—O3	123.8 (2)
C6—C5—H5	111.5	O2—C21—C1'	124.8 (2)
C11—C5—H5	111.5	O3—C21—C1'	111.4 (3)
C5—C6—C7	104.7 (2)	O8—C22—H22A	109.5
C5—C6—H6A	110.8	O8—C22—H22B	109.5
C7—C6—H6A	110.8	H22A—C22—H22B	109.5
C5—C6—H6B	110.8	O8—C22—H22C	109.5
C7—C6—H6B	110.8	H22A—C22—H22C	109.5
H6A—C6—H6B	108.9	H22B—C22—H22C	109.5
C8—C7—C6	111.5 (2)	O6—C23—H23A	109.5
C8—C7—C17	111.3 (2)	O6—C23—H23B	109.5
C6—C7—C17	102.8 (2)	H23A—C23—H23B	109.5
C8—C7—H7	110.3	O6—C23—H23C	109.5
C6—C7—H7	110.3	H23A—C23—H23C	109.5
C17—C7—H7	110.3	H23B—C23—H23C	109.5
O5—C8—C7	105.9 (2)	O7—C24—H24A	109.5
O5—C8—C15	107.5 (2)	O7—C24—H24B	109.5
C7—C8—C15	111.4 (2)	H24A—C24—H24B	109.5
O5—C8—C9	108.2 (2)	O7—C24—H24C	109.5
C7—C8—C9	110.1 (2)	H24A—C24—H24C	109.5
C15—C8—C9	113.5 (2)	H24B—C24—H24C	109.5
O4—C9—C14	110.6 (2)	N2—C25—C26	113.4 (3)
O4—C9—C10	108.9 (2)	N2—C25—H25A	108.9
C14—C9—C10	103.8 (2)	C26—C25—H25A	108.9
O4—C9—C8	112.2 (2)	N2—C25—H25B	108.9
C14—C9—C8	109.1 (2)	C26—C25—H25B	108.9
C10—C9—C8	111.9 (2)	H25A—C25—H25B	107.7
C9—C10—C11	117.8 (2)	C25—C26—H26A	109.5
C9—C10—C12	102.8 (2)	C25—C26—H26B	109.5
C11—C10—C12	115.4 (2)	H26A—C26—H26B	109.5
C9—C10—H10	106.7	C25—C26—H26C	109.5
C11—C10—H10	106.7	H26A—C26—H26C	109.5
C12—C10—H10	106.7	H26B—C26—H26C	109.5
C17—C11—C1	118.4 (2)	C6'—C1'—C2'	118.9 (3)
C17—C11—C5	97.84 (19)	C6'—C1'—C21	119.5 (3)
C1—C11—C5	111.0 (2)	C2'—C1'—C21	121.6 (3)
C17—C11—C10	109.3 (2)	C3'—C2'—N1	121.8 (3)
C1—C11—C10	107.8 (2)	C3'—C2'—C1'	118.9 (3)
C5—C11—C10	112.3 (2)	N1—C2'—C1'	119.4 (2)
C13—C12—C10	106.7 (2)	C4'—C3'—C2'	120.4 (3)
C13—C12—H12A	110.4	C4'—C3'—H3'	119.8
C10—C12—H12A	110.4	C2'—C3'—H3'	119.8
C13—C12—H12B	110.4	C3'—C4'—C5'	121.5 (3)
C10—C12—H12B	110.4	C3'—C4'—H4'	119.3
H12A—C12—H12B	108.6	C5'—C4'—H4'	119.3
C14—C13—C16	112.5 (2)	C6'—C5'—C4'	118.7 (3)
C14—C13—C12	100.9 (2)	C6'—C5'—H5'	120.7
C16—C13—C12	111.1 (2)	C4'—C5'—H5'	120.7
C14—C13—H13	110.6	C5'—C6'—C1'	121.6 (3)
C16—C13—H13	110.6	C5'—C6'—H6'	119.2
C12—C13—H13	110.6	C1'—C6'—H6'	119.2
O6—C14—C13	117.7 (2)	C19—N1—C2'	128.9 (2)
O6—C14—C9	109.1 (2)	C19—N1—H1A	115.5
C13—C14—C9	101.9 (2)	C2'—N1—H1A	115.5
O6—C14—H14	109.2	C25—N2—C17	112.2 (2)
C13—C14—H14	109.2	C25—N2—C18	110.5 (2)
C9—C14—H14	109.2	C17—N2—C18	116.3 (2)
C16—C15—C8	118.6 (2)	C21—O3—C4	121.3 (2)
C16—C15—H15A	107.7	C9—O4—H4	109.5
C8—C15—H15A	107.7	C8—O5—H5A	109.5
C16—C15—H15B	107.7	C23—O6—C14	113.6 (2)
C8—C15—H15B	107.7	C24—O7—C16	112.3 (3)
H15A—C15—H15B	107.1	C22—O8—C1	115.2 (3)

O8—C1—C2—C3	168.9 (2)	C8—C9—C14—O6	−52.2 (3)
C11—C1—C2—C3	43.8 (4)	O4—C9—C14—C13	−163.2 (2)
C1—C2—C3—C4	−53.7 (3)	C10—C9—C14—C13	−46.4 (3)
C2—C3—C4—O3	178.9 (2)	C8—C9—C14—C13	73.0 (3)
C2—C3—C4—C5	66.7 (3)	O5—C8—C15—C16	−138.9 (3)
C2—C3—C4—C18	−58.8 (3)	C7—C8—C15—C16	105.5 (3)
O3—C4—C5—C6	65.1 (2)	C9—C8—C15—C16	−19.4 (4)
C3—C4—C5—C6	−178.9 (2)	C14—C13—C16—O7	−98.1 (3)
C18—C4—C5—C6	−51.2 (3)	C12—C13—C16—O7	149.6 (2)
O3—C4—C5—C11	178.8 (2)	C14—C13—C16—C15	23.8 (3)
C3—C4—C5—C11	−65.1 (3)	C12—C13—C16—C15	−88.5 (3)
C18—C4—C5—C11	62.5 (3)	C8—C15—C16—O7	143.1 (3)
C4—C5—C6—C7	100.7 (2)	C8—C15—C16—C13	22.5 (4)
C11—C5—C6—C7	−14.9 (3)	C1—C11—C17—N2	−49.2 (3)
C5—C6—C7—C8	101.7 (2)	C5—C11—C17—N2	69.8 (2)
C5—C6—C7—C17	−17.7 (3)	C10—C11—C17—N2	−173.18 (18)
C6—C7—C8—O5	65.9 (3)	C1—C11—C17—C7	−171.6 (2)
C17—C7—C8—O5	−179.9 (2)	C5—C11—C17—C7	−52.5 (2)
C6—C7—C8—C15	−177.6 (2)	C10—C11—C17—C7	64.5 (2)
C17—C7—C8—C15	−63.4 (3)	C8—C7—C17—N2	165.6 (2)
C6—C7—C8—C9	−50.8 (3)	C6—C7—C17—N2	−74.9 (3)
C17—C7—C8—C9	63.4 (3)	C8—C7—C17—C11	−74.9 (2)
O5—C8—C9—O4	−33.0 (3)	C6—C7—C17—C11	44.6 (2)
C7—C8—C9—O4	82.3 (3)	O3—C4—C18—N2	−152.6 (2)
C15—C8—C9—O4	−152.1 (2)	C3—C4—C18—N2	85.3 (3)
O5—C8—C9—C14	90.0 (2)	C5—C4—C18—N2	−40.5 (3)
C7—C8—C9—C14	−154.8 (2)	O2—C21—C1'—C6'	173.3 (3)
C15—C8—C9—C14	−29.2 (3)	O3—C21—C1'—C6'	−6.6 (4)
O5—C8—C9—C10	−155.72 (19)	O2—C21—C1'—C2'	−5.2 (5)
C7—C8—C9—C10	−40.5 (3)	O3—C21—C1'—C2'	174.9 (3)
C15—C8—C9—C10	85.2 (3)	C6'—C1'—C2'—C3'	−1.5 (4)
O4—C9—C10—C11	−88.2 (3)	C21—C1'—C2'—C3'	177.0 (3)
C14—C9—C10—C11	153.9 (2)	C6'—C1'—C2'—N1	178.7 (3)
C8—C9—C10—C11	36.4 (3)	C21—C1'—C2'—N1	−2.9 (4)
O4—C9—C10—C12	143.8 (2)	N1—C2'—C3'—C4'	−178.5 (3)
C14—C9—C10—C12	25.9 (3)	C1'—C2'—C3'—C4'	1.6 (5)
C8—C9—C10—C12	−91.6 (2)	C2'—C3'—C4'—C5'	−0.4 (5)
O8—C1—C11—C17	−54.3 (3)	C3'—C4'—C5'—C6'	−1.0 (5)
C2—C1—C11—C17	69.8 (3)	C4'—C5'—C6'—C1'	1.1 (5)
O8—C1—C11—C5	−166.3 (2)	C2'—C1'—C6'—C5'	0.1 (5)
C2—C1—C11—C5	−42.2 (3)	C21—C1'—C6'—C5'	−178.4 (3)
O8—C1—C11—C10	70.4 (3)	O1—C19—N1—C2'	0.7 (5)
C2—C1—C11—C10	−165.6 (2)	C20—C19—N1—C2'	−178.9 (3)
C4—C5—C11—C17	−74.2 (2)	C3'—C2'—N1—C19	11.0 (5)
C6—C5—C11—C17	41.9 (2)	C1'—C2'—N1—C19	−169.1 (3)
C4—C5—C11—C1	50.3 (3)	C26—C25—N2—C17	−164.6 (2)
C6—C5—C11—C1	166.5 (2)	C26—C25—N2—C18	63.8 (3)
C4—C5—C11—C10	171.1 (2)	C11—C17—N2—C25	176.1 (2)
C6—C5—C11—C10	−72.7 (3)	C7—C17—N2—C25	−70.3 (3)
C9—C10—C11—C17	−51.1 (3)	C11—C17—N2—C18	−55.3 (3)
C12—C10—C11—C17	70.7 (3)	C7—C17—N2—C18	58.3 (3)
C9—C10—C11—C1	178.9 (2)	C4—C18—N2—C25	166.6 (2)
C12—C10—C11—C1	−59.3 (3)	C4—C18—N2—C17	37.2 (3)
C9—C10—C11—C5	56.3 (3)	O2—C21—O3—C4	1.0 (5)
C12—C10—C11—C5	178.1 (2)	C1'—C21—O3—C4	−179.1 (2)
C9—C10—C12—C13	3.1 (3)	C3—C4—O3—C21	65.8 (3)
C11—C10—C12—C13	−126.5 (2)	C5—C4—O3—C21	−176.6 (2)
C10—C12—C13—C14	−30.9 (3)	C18—C4—O3—C21	−59.5 (3)
C10—C12—C13—C16	88.6 (3)	C13—C14—O6—C23	68.1 (3)
C16—C13—C14—O6	47.8 (3)	C9—C14—O6—C23	−176.6 (3)
C12—C13—C14—O6	166.3 (2)	C13—C16—O7—C24	−165.8 (3)
C16—C13—C14—C9	−71.4 (3)	C15—C16—O7—C24	70.4 (4)
C12—C13—C14—C9	47.1 (3)	C2—C1—O8—C22	75.0 (4)
O4—C9—C14—O6	71.7 (3)	C11—C1—O8—C22	−155.8 (3)
C10—C9—C14—O6	−171.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.86	1.97	2.668 (3)	138
O4—H4···O5	0.82	2.23	2.665 (3)	113
O5—H5A···O6	0.82	2.30	2.875 (3)	127

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