2-(2′,3′,4′,6′-Tetra-O-acetyl-β-D-gluco­pyran­osyl­thio)-4-pyridin-4-yl-6,7,8,9-tetra­hydro-5H-cyclo­hepta­[b]­pyridine-3-carbo­nitrile

In the title compound, C₃₀H₃₃N₃O₉S, the glucoside moiety is attached to the pyridone via the S atom. The expected absolute configuration was confirmed. Dimensions at sulfur are S—C(pyridone) 1.780 (2), S—C(glucoside) 1.803 (2) Å, C—S—C 98.15 (11)°. There are three short H...O contacts (<2.5 Å) that determine the molecular packing.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.111
• Data-to-parameter ratio = 18.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_371  Alert C Long   C(sp2)-C(sp1) Bond  C(3)   -   C(12)  =       1.44 Ang.

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     31
                   C4  -C3  -C12 -N13   126.00 12.00   1.555   1.555   1.555   1.555

PLAT_710  Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle #     32
                   C2  -C3  -C12 -N13   -53.00 12.00   1.555   1.555   1.555   1.555

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               7289
         Count of symmetry unique reflns         4155
         Completeness (_total/calc)            175.43%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      3134
         Fraction of Friedel pairs measured     0.754
         Are heavy atom types Z>Si present          yes
          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.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 3 Alert Level C = Please check

---

Computing details

Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

2-(2',3',4',6'-Tetra-O-acetyl-β-D-glucopyranosylthio)-4-pyridin-4-yl- 6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carbonitrile

Crystal data

C30H33N3O9S	Dx = 1.281 Mg m^−3
Mr = 611.65	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 61 reflections
a = 8.0237 (14) Å	θ = 4.5–12.5°
b = 10.2293 (14) Å	µ = 0.16 mm^−1
c = 38.636 (6) Å	T = 173 K
V = 3171.1 (9) Å^3	Tablet, colourless
Z = 4	0.60 × 0.45 × 0.25 mm
F(000) = 1288

Data collection

Siemens P4 diffractometer	Rint = 0.022
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 3.2°
Graphite monochromator	h = −10→10
ω–scans	k = −13→0
7824 measured reflections	l = 0→50
7289 independent reflections	3 standard reflections every 247 reflections
5529 reflections with I > 2σ(I)	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0643P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max = 0.018
7289 reflections	Δρmax = 0.43 e Å^−3
392 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (8)

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.3626 (0.0187) x + 5.2939 (0.0127) y + 31.0403 (0.0432) z = 28.5469 (0.0330)

* -0.0107 (0.0009) C5 * 0.0109 (0.0009) C9 * -0.0229 (0.0019) C10 * 0.0227 (0.0019) C11 - 1.2242 (0.0061) C6 - 1.2060 (0.0073) C7 - 1.1798 (0.0060) C8

Rms deviation of fitted atoms = 0.0178

- 2.3734 (0.0457) x + 5.4440 (0.0190) y + 30.6484 (0.0889) z = 27.1271 (0.0634)

Angle to previous plane (with approximate e.s.d.) = 1.02 (0.42)

* 0.0000 (0.0000) C6 * 0.0000 (0.0000) C7 * 0.0000 (0.0000) C8

Rms deviation of fitted atoms = 0.0000

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
S	0.60092 (7)	0.49702 (6)	0.878323 (16)	0.03099 (13)
O1	0.37769 (19)	0.42109 (14)	0.92324 (4)	0.0277 (3)
O2	0.64631 (18)	0.18940 (15)	0.87778 (4)	0.0304 (4)
O3	0.5351 (2)	0.04489 (14)	0.93768 (4)	0.0304 (4)
O4	0.2138 (2)	0.11383 (15)	0.95799 (4)	0.0341 (4)
O5	0.0610 (2)	0.51253 (18)	0.93864 (5)	0.0414 (4)
O6	0.8998 (3)	0.2544 (3)	0.89351 (7)	0.0785 (8)
O7	0.4022 (3)	−0.09843 (16)	0.90312 (4)	0.0432 (4)
O8	0.2244 (3)	0.1743 (2)	1.01388 (5)	0.0497 (5)
O9	0.2129 (3)	0.66015 (19)	0.96802 (5)	0.0523 (5)
N1	0.2985 (3)	0.52590 (19)	0.84962 (6)	0.0386 (5)
C2	0.4462 (3)	0.5818 (2)	0.85412 (6)	0.0297 (5)
C3	0.4818 (3)	0.7062 (2)	0.84100 (6)	0.0266 (5)
C4	0.3653 (3)	0.7689 (2)	0.82020 (6)	0.0331 (5)
C5	0.0740 (4)	0.7722 (3)	0.79327 (9)	0.0528 (8)
H5A	−0.0228	0.7914	0.8083	0.063*
H5B	0.1161	0.8566	0.7843	0.063*
C6	0.0156 (5)	0.6917 (4)	0.76345 (9)	0.0723 (10)
H6A	0.1137	0.6502	0.7525	0.087*
H6B	−0.0356	0.7505	0.7461	0.087*
C7	−0.1100 (5)	0.5851 (3)	0.77267 (9)	0.0672 (9)
H7A	−0.2078	0.6266	0.7838	0.081*
H7B	−0.1489	0.5435	0.7510	0.081*
C8	−0.0437 (4)	0.4786 (3)	0.79671 (10)	0.0707 (10)
H8A	−0.1322	0.4122	0.8000	0.085*
H8B	0.0514	0.4350	0.7852	0.085*
C9	0.0117 (3)	0.5247 (3)	0.83142 (9)	0.0523 (8)
H9A	0.0150	0.4488	0.8473	0.063*
H9B	−0.0724	0.5867	0.8405	0.063*
C10	0.1800 (3)	0.5906 (3)	0.83190 (7)	0.0407 (6)
C11	0.2089 (3)	0.7105 (3)	0.81512 (7)	0.0403 (6)
C12	0.6375 (3)	0.7688 (2)	0.84973 (6)	0.0310 (5)
N13	0.7596 (3)	0.8178 (2)	0.85719 (7)	0.0454 (6)
C14	0.4056 (3)	0.9003 (2)	0.80537 (6)	0.0328 (5)
C15	0.4877 (4)	0.9112 (3)	0.77388 (7)	0.0430 (6)
H15	0.5193	0.8356	0.7612	0.052*
C16	0.5222 (4)	1.0348 (3)	0.76147 (8)	0.0530 (8)
H16	0.5783	1.0410	0.7399	0.064*
N17	0.4835 (4)	1.1445 (2)	0.77724 (7)	0.0569 (7)
C18	0.4039 (6)	1.1327 (3)	0.80750 (8)	0.0648 (10)
H18	0.3732	1.2104	0.8194	0.078*
C19	0.3636 (4)	1.0138 (3)	0.82255 (7)	0.0513 (8)
H19	0.3082	1.0105	0.8443	0.062*
C20	0.4705 (3)	0.3686 (2)	0.89534 (6)	0.0250 (5)
H20	0.3915	0.3397	0.8768	0.030*
C21	0.5714 (3)	0.2505 (2)	0.90755 (6)	0.0249 (5)
H21	0.6568	0.2756	0.9252	0.030*
C22	0.4460 (3)	0.1521 (2)	0.92205 (6)	0.0260 (5)
H22	0.3760	0.1179	0.9027	0.031*
C23	0.3333 (3)	0.2134 (2)	0.94904 (6)	0.0271 (5)
H23	0.3995	0.2392	0.9699	0.033*
C24	0.2474 (3)	0.3324 (2)	0.93358 (6)	0.0299 (5)
H24	0.1830	0.3049	0.9126	0.036*
C30	0.1334 (3)	0.4050 (2)	0.95776 (7)	0.0378 (6)
H30A	0.0446	0.3461	0.9663	0.045*
H30B	0.1969	0.4383	0.9779	0.045*
C31	0.8125 (3)	0.1985 (3)	0.87389 (8)	0.0404 (6)
C32	0.4965 (3)	−0.0777 (2)	0.92633 (6)	0.0337 (6)
C33	0.1739 (3)	0.1009 (3)	0.99221 (7)	0.0371 (6)
C34	0.1195 (3)	0.6331 (2)	0.94491 (7)	0.0398 (6)
C35	0.8684 (4)	0.1336 (3)	0.84150 (8)	0.0544 (8)
H35A	0.9894	0.1427	0.8392	0.082*
H35B	0.8134	0.1746	0.8216	0.082*
H35C	0.8391	0.0406	0.8423	0.082*
C36	0.5863 (4)	−0.1782 (2)	0.94682 (8)	0.0510 (7)
H36A	0.5232	−0.1975	0.9679	0.077*
H36B	0.6970	−0.1454	0.9530	0.077*
H36C	0.5978	−0.2581	0.9330	0.077*
C37	0.0610 (4)	−0.0132 (3)	0.99696 (8)	0.0641 (10)
H37A	0.1169	−0.0928	0.9889	0.096*
H37B	−0.0413	0.0004	0.9836	0.096*
H37C	0.0331	−0.0224	1.0215	0.096*
C38	0.0523 (4)	0.7278 (3)	0.91904 (9)	0.0583 (8)
H38A	0.0242	0.8101	0.9307	0.088*
H38B	−0.0479	0.6913	0.9083	0.088*
H38C	0.1366	0.7443	0.9012	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0260 (2)	0.0266 (3)	0.0404 (3)	−0.0020 (3)	−0.0022 (3)	0.0103 (3)
O1	0.0273 (8)	0.0236 (7)	0.0324 (8)	−0.0019 (7)	0.0022 (7)	0.0005 (6)
O2	0.0286 (8)	0.0297 (8)	0.0329 (8)	−0.0016 (6)	0.0038 (7)	−0.0010 (7)
O3	0.0369 (9)	0.0236 (8)	0.0308 (8)	0.0009 (7)	−0.0031 (7)	0.0037 (7)
O4	0.0398 (9)	0.0316 (9)	0.0308 (9)	−0.0115 (8)	0.0083 (7)	−0.0031 (7)
O5	0.0338 (9)	0.0404 (10)	0.0500 (10)	0.0091 (8)	−0.0030 (8)	−0.0022 (9)
O6	0.0296 (11)	0.113 (2)	0.0930 (18)	−0.0122 (13)	−0.0010 (12)	−0.0369 (16)
O7	0.0637 (12)	0.0300 (9)	0.0359 (10)	−0.0035 (10)	−0.0083 (10)	−0.0049 (8)
O8	0.0625 (13)	0.0567 (12)	0.0300 (9)	−0.0102 (11)	0.0113 (9)	−0.0045 (9)
O9	0.0686 (13)	0.0436 (11)	0.0448 (11)	−0.0002 (11)	−0.0083 (11)	−0.0048 (9)
N1	0.0357 (11)	0.0316 (11)	0.0487 (13)	−0.0045 (9)	−0.0093 (10)	0.0125 (10)
C2	0.0293 (11)	0.0283 (11)	0.0316 (12)	0.0003 (9)	−0.0022 (10)	0.0044 (10)
C3	0.0270 (11)	0.0251 (11)	0.0277 (11)	0.0000 (9)	0.0011 (9)	0.0006 (9)
C4	0.0387 (14)	0.0262 (12)	0.0343 (13)	0.0002 (10)	−0.0039 (11)	0.0023 (10)
C5	0.0462 (17)	0.0462 (16)	0.0661 (19)	−0.0037 (14)	−0.0157 (15)	0.0182 (15)
C6	0.068 (2)	0.085 (3)	0.064 (2)	0.004 (2)	−0.0282 (19)	0.011 (2)
C7	0.0564 (19)	0.070 (2)	0.075 (2)	−0.0084 (19)	−0.0307 (18)	−0.0021 (19)
C8	0.0603 (19)	0.054 (2)	0.098 (3)	−0.0101 (17)	−0.032 (2)	−0.005 (2)
C9	0.0404 (14)	0.0435 (17)	0.073 (2)	−0.0049 (13)	−0.0074 (14)	0.0131 (15)
C10	0.0349 (13)	0.0384 (14)	0.0487 (16)	−0.0023 (12)	−0.0054 (12)	0.0023 (13)
C11	0.0388 (14)	0.0371 (14)	0.0450 (15)	−0.0023 (12)	−0.0091 (12)	0.0076 (12)
C12	0.0353 (13)	0.0228 (11)	0.0350 (13)	0.0030 (10)	−0.0003 (11)	0.0052 (10)
N13	0.0376 (13)	0.0357 (12)	0.0630 (15)	−0.0071 (10)	−0.0111 (12)	0.0107 (11)
C14	0.0377 (13)	0.0268 (11)	0.0338 (13)	−0.0008 (11)	−0.0117 (11)	0.0056 (10)
C15	0.0464 (15)	0.0326 (13)	0.0502 (16)	0.0014 (12)	0.0031 (13)	0.0073 (13)
C16	0.0529 (17)	0.0488 (18)	0.0574 (19)	−0.0078 (14)	0.0003 (15)	0.0204 (15)
N17	0.0739 (18)	0.0380 (14)	0.0587 (17)	−0.0164 (13)	−0.0271 (15)	0.0159 (12)
C18	0.117 (3)	0.0288 (14)	0.0487 (19)	−0.0054 (18)	−0.030 (2)	0.0007 (13)
C19	0.088 (2)	0.0362 (14)	0.0297 (13)	0.0044 (16)	−0.0110 (14)	0.0005 (12)
C20	0.0259 (11)	0.0216 (10)	0.0275 (11)	−0.0027 (9)	0.0004 (9)	0.0038 (9)
C21	0.0233 (11)	0.0258 (11)	0.0255 (11)	−0.0007 (9)	−0.0023 (9)	0.0008 (9)
C22	0.0303 (12)	0.0216 (10)	0.0262 (11)	−0.0015 (9)	−0.0036 (9)	0.0031 (9)
C23	0.0276 (11)	0.0276 (11)	0.0263 (11)	−0.0065 (9)	0.0009 (9)	0.0020 (9)
C24	0.0263 (11)	0.0312 (12)	0.0322 (12)	−0.0026 (10)	0.0012 (10)	−0.0023 (10)
C30	0.0350 (14)	0.0378 (13)	0.0406 (14)	0.0060 (12)	0.0075 (12)	0.0025 (12)
C31	0.0311 (13)	0.0344 (13)	0.0557 (17)	0.0005 (11)	0.0092 (13)	0.0029 (13)
C32	0.0459 (15)	0.0260 (12)	0.0292 (12)	0.0015 (11)	0.0078 (11)	0.0006 (10)
C33	0.0426 (14)	0.0320 (13)	0.0366 (14)	0.0019 (12)	0.0139 (11)	0.0022 (11)
C34	0.0392 (14)	0.0404 (14)	0.0397 (14)	0.0127 (12)	0.0036 (13)	−0.0072 (12)
C35	0.0467 (17)	0.0448 (16)	0.072 (2)	−0.0011 (13)	0.0281 (16)	−0.0024 (14)
C36	0.076 (2)	0.0284 (13)	0.0486 (16)	0.0112 (14)	−0.0056 (16)	0.0065 (12)
C37	0.085 (2)	0.0420 (17)	0.066 (2)	−0.0126 (17)	0.0454 (18)	0.0000 (15)
C38	0.068 (2)	0.0476 (17)	0.0599 (19)	0.0109 (16)	−0.0065 (17)	0.0033 (15)

Geometric parameters (Å, º)

S—C2	1.780 (2)	C12—N13	1.138 (3)
S—C20	1.803 (2)	C14—C19	1.379 (4)
O1—C20	1.416 (3)	C14—C15	1.388 (4)
O1—C24	1.441 (3)	C15—C16	1.380 (4)
O2—C31	1.345 (3)	C15—H15	0.9500
O2—C21	1.440 (3)	C16—N17	1.315 (4)
O3—C32	1.364 (3)	C16—H16	0.9500
O3—C22	1.442 (3)	N17—C18	1.338 (4)
O4—C33	1.367 (3)	C18—C19	1.387 (4)
O4—C23	1.441 (3)	C18—H18	0.9500
O5—C34	1.342 (3)	C19—H19	0.9500
O5—C30	1.447 (3)	C20—C21	1.529 (3)
O6—C31	1.179 (3)	C20—H20	1.0000
O7—C32	1.192 (3)	C21—C22	1.529 (3)
O8—C33	1.195 (3)	C21—H21	1.0000
O9—C34	1.198 (3)	C22—C23	1.516 (3)
N1—C2	1.327 (3)	C22—H22	1.0000
N1—C10	1.346 (3)	C23—C24	1.521 (3)
C2—C3	1.399 (3)	C23—H23	1.0000
C3—C4	1.390 (3)	C24—C30	1.504 (3)
C3—C12	1.444 (3)	C24—H24	1.0000
C4—C11	1.404 (4)	C30—H30A	0.9900
C4—C14	1.496 (3)	C30—H30B	0.9900
C5—C6	1.492 (5)	C31—C35	1.486 (4)
C5—C11	1.510 (4)	C32—C36	1.484 (4)
C5—H5A	0.9900	C33—C37	1.489 (4)
C5—H5B	0.9900	C34—C38	1.493 (4)
C6—C7	1.527 (5)	C35—H35A	0.9800
C6—H6A	0.9900	C35—H35B	0.9800
C6—H6B	0.9900	C35—H35C	0.9800
C7—C8	1.527 (5)	C36—H36A	0.9800
C7—H7A	0.9900	C36—H36B	0.9800
C7—H7B	0.9900	C36—H36C	0.9800
C8—C9	1.490 (5)	C37—H37A	0.9800
C8—H8A	0.9900	C37—H37B	0.9800
C8—H8B	0.9900	C37—H37C	0.9800
C9—C10	1.510 (4)	C38—H38A	0.9800
C9—H9A	0.9900	C38—H38B	0.9800
C9—H9B	0.9900	C38—H38C	0.9800
C10—C11	1.407 (4)
C2—S—C20	98.15 (11)	C21—C20—S	112.40 (15)
C20—O1—C24	110.72 (16)	O1—C20—H20	108.8
C31—O2—C21	118.2 (2)	C21—C20—H20	108.8
C32—O3—C22	116.89 (18)	S—C20—H20	108.8
C33—O4—C23	117.14 (19)	O2—C21—C20	108.50 (17)
C34—O5—C30	117.8 (2)	O2—C21—C22	106.38 (17)
C2—N1—C10	119.1 (2)	C20—C21—C22	106.52 (17)
N1—C2—C3	121.7 (2)	O2—C21—H21	111.7
N1—C2—S	118.82 (17)	C20—C21—H21	111.7
C3—C2—S	119.42 (17)	C22—C21—H21	111.7
C4—C3—C2	119.5 (2)	O3—C22—C23	108.80 (18)
C4—C3—C12	120.8 (2)	O3—C22—C21	109.10 (17)
C2—C3—C12	119.7 (2)	C23—C22—C21	111.88 (18)
C3—C4—C11	119.1 (2)	O3—C22—H22	109.0
C3—C4—C14	119.4 (2)	C23—C22—H22	109.0
C11—C4—C14	121.5 (2)	C21—C22—H22	109.0
C6—C5—C11	115.2 (3)	O4—C23—C22	105.63 (17)
C6—C5—H5A	108.5	O4—C23—C24	110.98 (18)
C11—C5—H5A	108.5	C22—C23—C24	109.32 (18)
C6—C5—H5B	108.5	O4—C23—H23	110.3
C11—C5—H5B	108.5	C22—C23—H23	110.3
H5A—C5—H5B	107.5	C24—C23—H23	110.3
C5—C6—C7	114.9 (3)	O1—C24—C30	107.60 (19)
C5—C6—H6A	108.5	O1—C24—C23	106.49 (17)
C7—C6—H6A	108.5	C30—C24—C23	115.3 (2)
C5—C6—H6B	108.5	O1—C24—H24	109.1
C7—C6—H6B	108.5	C30—C24—H24	109.1
H6A—C6—H6B	107.5	C23—C24—H24	109.1
C8—C7—C6	114.9 (3)	O5—C30—C24	107.6 (2)
C8—C7—H7A	108.5	O5—C30—H30A	110.2
C6—C7—H7A	108.5	C24—C30—H30A	110.2
C8—C7—H7B	108.5	O5—C30—H30B	110.2
C6—C7—H7B	108.5	C24—C30—H30B	110.2
H7A—C7—H7B	107.5	H30A—C30—H30B	108.5
C9—C8—C7	115.2 (3)	O6—C31—O2	123.4 (3)
C9—C8—H8A	108.5	O6—C31—C35	125.4 (3)
C7—C8—H8A	108.5	O2—C31—C35	111.2 (3)
C9—C8—H8B	108.5	O7—C32—O3	123.3 (2)
C7—C8—H8B	108.5	O7—C32—C36	125.9 (2)
H8A—C8—H8B	107.5	O3—C32—C36	110.8 (2)
C8—C9—C10	114.8 (3)	O8—C33—O4	122.5 (2)
C8—C9—H9A	108.6	O8—C33—C37	127.8 (3)
C10—C9—H9A	108.6	O4—C33—C37	109.7 (2)
C8—C9—H9B	108.6	O9—C34—O5	124.4 (2)
C10—C9—H9B	108.6	O9—C34—C38	125.1 (3)
H9A—C9—H9B	107.5	O5—C34—C38	110.5 (2)
N1—C10—C11	123.2 (2)	C31—C35—H35A	109.5
N1—C10—C9	114.7 (2)	C31—C35—H35B	109.5
C11—C10—C9	122.1 (2)	H35A—C35—H35B	109.5
C4—C11—C10	117.0 (2)	C31—C35—H35C	109.5
C4—C11—C5	122.8 (2)	H35A—C35—H35C	109.5
C10—C11—C5	120.3 (2)	H35B—C35—H35C	109.5
N13—C12—C3	178.8 (3)	C32—C36—H36A	109.5
C19—C14—C15	118.0 (2)	C32—C36—H36B	109.5
C19—C14—C4	121.3 (2)	H36A—C36—H36B	109.5
C15—C14—C4	120.7 (2)	C32—C36—H36C	109.5
C16—C15—C14	118.3 (3)	H36A—C36—H36C	109.5
C16—C15—H15	120.9	H36B—C36—H36C	109.5
C14—C15—H15	120.9	C33—C37—H37A	109.5
N17—C16—C15	125.0 (3)	C33—C37—H37B	109.5
N17—C16—H16	117.5	H37A—C37—H37B	109.5
C15—C16—H16	117.5	C33—C37—H37C	109.5
C16—N17—C18	116.1 (3)	H37A—C37—H37C	109.5
N17—C18—C19	123.8 (3)	H37B—C37—H37C	109.5
N17—C18—H18	118.1	C34—C38—H38A	109.5
C19—C18—H18	118.1	C34—C38—H38B	109.5
C14—C19—C18	118.7 (3)	H38A—C38—H38B	109.5
C14—C19—H19	120.7	C34—C38—H38C	109.5
C18—C19—H19	120.7	H38A—C38—H38C	109.5
O1—C20—C21	110.08 (17)	H38B—C38—H38C	109.5
O1—C20—S	107.84 (14)
C10—N1—C2—C3	0.1 (4)	C4—C14—C19—C18	−179.9 (3)
C10—N1—C2—S	178.7 (2)	N17—C18—C19—C14	−0.8 (5)
C20—S—C2—N1	−10.7 (2)	C24—O1—C20—C21	−68.6 (2)
C20—S—C2—C3	167.95 (19)	C24—O1—C20—S	168.46 (14)
N1—C2—C3—C4	−5.6 (4)	C2—S—C20—O1	−78.05 (16)
S—C2—C3—C4	175.83 (18)	C2—S—C20—C21	160.43 (17)
N1—C2—C3—C12	173.3 (2)	C31—O2—C21—C20	110.0 (2)
S—C2—C3—C12	−5.3 (3)	C31—O2—C21—C22	−135.8 (2)
C2—C3—C4—C11	5.1 (4)	O1—C20—C21—O2	172.45 (16)
C12—C3—C4—C11	−173.7 (2)	S—C20—C21—O2	−67.3 (2)
C2—C3—C4—C14	−178.2 (2)	O1—C20—C21—C22	58.3 (2)
C12—C3—C4—C14	2.9 (3)	S—C20—C21—C22	178.51 (15)
C11—C5—C6—C7	80.5 (4)	C32—O3—C22—C23	112.3 (2)
C5—C6—C7—C8	−63.8 (4)	C32—O3—C22—C21	−125.4 (2)
C6—C7—C8—C9	61.4 (5)	O2—C21—C22—O3	71.0 (2)
C7—C8—C9—C10	−77.5 (4)	C20—C21—C22—O3	−173.38 (17)
C2—N1—C10—C11	5.8 (4)	O2—C21—C22—C23	−168.55 (17)
C2—N1—C10—C9	−174.0 (3)	C20—C21—C22—C23	−52.9 (2)
C8—C9—C10—N1	−114.2 (3)	C33—O4—C23—C22	138.5 (2)
C8—C9—C10—C11	66.0 (4)	C33—O4—C23—C24	−103.1 (2)
C3—C4—C11—C10	0.4 (4)	O3—C22—C23—O4	−64.3 (2)
C14—C4—C11—C10	−176.2 (2)	C21—C22—C23—O4	175.06 (17)
C3—C4—C11—C5	179.4 (3)	O3—C22—C23—C24	176.19 (17)
C14—C4—C11—C5	2.8 (4)	C21—C22—C23—C24	55.6 (2)
N1—C10—C11—C4	−6.0 (4)	C20—O1—C24—C30	−168.38 (18)
C9—C10—C11—C4	173.8 (3)	C20—O1—C24—C23	67.5 (2)
N1—C10—C11—C5	175.0 (3)	O4—C23—C24—O1	−175.80 (17)
C9—C10—C11—C5	−5.2 (4)	C22—C23—C24—O1	−59.7 (2)
C6—C5—C11—C4	121.1 (3)	O4—C23—C24—C30	65.0 (3)
C6—C5—C11—C10	−59.9 (4)	C22—C23—C24—C30	−178.9 (2)
C4—C3—C12—N13	126 (12)	C34—O5—C30—C24	−104.6 (2)
C2—C3—C12—N13	−53 (12)	O1—C24—C30—O5	62.4 (2)
C3—C4—C14—C19	−91.6 (3)	C23—C24—C30—O5	−178.97 (19)
C11—C4—C14—C19	85.0 (3)	C21—O2—C31—O6	−0.3 (4)
C3—C4—C14—C15	88.0 (3)	C21—O2—C31—C35	−178.5 (2)
C11—C4—C14—C15	−95.4 (3)	C22—O3—C32—O7	4.8 (3)
C19—C14—C15—C16	−0.2 (4)	C22—O3—C32—C36	−174.9 (2)
C4—C14—C15—C16	−179.8 (3)	C23—O4—C33—O8	5.7 (4)
C14—C15—C16—N17	0.1 (5)	C23—O4—C33—C37	−175.1 (2)
C15—C16—N17—C18	−0.3 (5)	C30—O5—C34—O9	−9.4 (4)
C16—N17—C18—C19	0.7 (5)	C30—O5—C34—C38	170.5 (2)
C15—C14—C19—C18	0.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37C···O1^i	0.98	2.68	3.544 (3)	147
C24—H24···O6^ii	1.00	2.45	3.288 (3)	142
C19—H19···O7^iii	0.95	2.64	3.332 (3)	130
C38—H38C···O7^iii	0.98	2.67	3.379 (4)	129
C21—H21···O8^iv	1.00	2.47	3.364 (3)	149
C5—H5A···N13^ii	0.99	2.59	3.561 (4)	168
C35—H35C···N13^v	0.98	2.44	3.401 (4)	168
C15—H15···N17^vi	0.95	2.45	3.375 (4)	163

Symmetry codes: (i) x−1/2, −y+1/2, −z+2; (ii) x−1, y, z; (iii) x, y+1, z; (iv) x+1/2, −y+1/2, −z+2; (v) x, y−1, z; (vi) −x+1, y−1/2, −z+3/2.