Methyl 2-methyl-6-methyl­thio-1,3-dioxo-4-[(2,3,4,6-tetra-O-acetyl-[beta]-D-gluco­pyran­osyl)­amino]-2,3-di­hydro-1H-pyrrolo­[3,4-c]­pyridine-7-carboxyl­ate

The title compound, C₂₅H₂₉N₃O₁₃S, has peripheral acetyl and carbo­methoxy groups which show disorder. The absolute structure, although known from the starting materials, was confirmed by the analysis. There are no intermolecular hydrogen bonds. This structure is of importance because it elucidates the pathway for hetero-Diels-Alder reactions between di­methyl acetyl­enedi­carboxyl­ate and 6-amino­pyridin-4(3H)-one derivatives catalyzed by tri­fluoro­acetic acid.

Computing details

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Methyl 2-methyl-6-methylthio-1,3-dioxo-4-[(2,3,4,6-tetra-O-acetyl-β-D– glucopyranosyl)amino]-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carboxylate

Crystal data

C25H29N3O13S	Dx = 1.332 Mg m^−3
Mr = 611.57	Melting point: 481 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.1696 (9) Å	Cell parameters from 4963 reflections
b = 6.9695 (7) Å	θ = 2.2–26.3°
c = 21.526 (2) Å	µ = 0.17 mm^−1
β = 92.036 (5)°	T = 150 K
V = 1524.7 (3) Å^3	Plate, yellow
Z = 2	0.25 × 0.1 × 0.1 mm
F(000) = 640

Data collection

KappaCCD diffractometer	4963 independent reflections
Radiation source: fine-focus sealed X-ray tube	2950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
φ and ω scans with κ offsets	θmax = 26.3°, θmin = 2.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	h = −12→12
Tmin = 0.958, Tmax = 0.983	k = −6→8
10860 measured reflections	l = −26→26

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)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0795P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max = 0.005
4963 reflections	Δρmax = 0.27 e Å^−3
378 parameters	Δρmin = −0.28 e Å^−3
4 restraints	Absolute structure: Flack (1983), 2844 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (15)

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	−0.2682 (5)	−0.0651 (9)	−0.5476 (3)	0.0394 (13)
O1	−0.2645 (3)	−0.0447 (6)	−0.60250 (17)	0.0481 (10)
N2	−0.3861 (4)	−0.0885 (7)	−0.51609 (19)	0.0369 (12)
C21	−0.5134 (5)	−0.1032 (9)	−0.5491 (2)	0.0469 (16)
C3	−0.3664 (5)	−0.0869 (8)	−0.4519 (2)	0.0333 (13)
O3	−0.4534 (3)	−0.1040 (5)	−0.41460 (16)	0.0412 (10)
C4	−0.0238 (5)	−0.0494 (9)	−0.4934 (2)	0.0332 (12)
O41	0.1686 (5)	0.0193 (12)	−0.5509 (3)	0.038 (2)*	0.711 (16)
O41A	0.1701 (10)	−0.102 (3)	−0.5510 (7)	0.053 (6)*	0.289 (16)
C41	0.0553 (5)	−0.0473 (9)	−0.5508 (3)	0.0393 (14)
O42	−0.0075 (5)	−0.1201 (12)	−0.5992 (2)	0.035 (2)*	0.711 (16)
O42A	−0.0145 (11)	−0.023 (3)	−0.6026 (4)	0.047 (6)*	0.289 (16)
C42	0.0556 (6)	−0.0897 (12)	−0.6573 (2)	0.064 (2)
C5	0.0397 (4)	−0.0551 (9)	−0.4334 (2)	0.0335 (12)
S5	0.21136 (12)	−0.0540 (2)	−0.42639 (7)	0.0423 (4)
C51	0.2369 (5)	−0.0838 (11)	−0.3438 (2)	0.0577 (19)
N6	−0.0256 (4)	−0.0546 (8)	−0.38019 (18)	0.0371 (11)
C7	−0.1593 (5)	−0.0600 (8)	−0.3839 (2)	0.0337 (12)
N7	−0.2245 (4)	−0.0560 (7)	−0.33035 (17)	0.0336 (10)
O7	−0.1373 (3)	−0.2294 (5)	−0.24636 (16)	0.0380 (10)
C71	−0.1671 (5)	−0.0437 (9)	−0.2691 (2)	0.0383 (13)
C72	−0.2670 (5)	0.0447 (8)	−0.2263 (2)	0.0350 (14)
O721	−0.2872 (3)	0.2466 (5)	−0.24187 (16)	0.0387 (10)
C721	−0.3988 (6)	0.2919 (10)	−0.2760 (3)	0.0436 (16)
C722	−0.4138 (6)	0.4993 (8)	−0.2834 (3)	0.0551 (18)
O722	−0.4772 (4)	0.1695 (6)	−0.29357 (18)	0.0502 (11)
C73	−0.2194 (5)	0.0394 (9)	−0.1574 (3)	0.0363 (14)
O731	−0.3296 (3)	0.1033 (6)	−0.12282 (17)	0.0461 (11)
C731	−0.3070 (7)	0.2424 (11)	−0.0796 (3)	0.0594 (19)
C732	−0.4329 (7)	0.2874 (12)	−0.0476 (4)	0.103 (3)
O732	−0.2014 (5)	0.3132 (8)	−0.0695 (2)	0.095 (2)
C74	−0.1814 (5)	−0.1620 (9)	−0.1400 (2)	0.0382 (15)
O741	−0.1241 (4)	−0.1642 (6)	−0.07900 (17)	0.0493 (11)
C741	−0.2026 (7)	−0.2204 (10)	−0.0323 (3)	0.0547 (18)
C742	−0.1241 (8)	−0.2292 (16)	0.0287 (3)	0.116 (4)
O742	−0.3159 (5)	−0.2534 (8)	−0.0389 (2)	0.0727 (15)
C75	−0.0781 (5)	−0.2312 (8)	−0.1848 (2)	0.0397 (15)
C751	−0.0349 (5)	−0.4340 (9)	−0.1719 (3)	0.0385 (15)
O751	0.0924 (3)	−0.4557 (7)	−0.1991 (2)	0.0508 (12)
C752	0.1375 (6)	−0.6339 (11)	−0.2043 (3)	0.0472 (17)
C753	0.2694 (6)	−0.6396 (11)	−0.2336 (3)	0.075 (2)
O752	0.0779 (4)	−0.7718 (7)	−0.1892 (2)	0.0557 (12)
C8	−0.1626 (5)	−0.0593 (8)	−0.4953 (2)	0.0314 (12)
C9	−0.2256 (4)	−0.0661 (8)	−0.4401 (2)	0.0286 (12)
H21A	−0.5783	−0.1561	−0.5212	0.070*	0.50
H21B	−0.5057	−0.1879	−0.5851	0.070*	0.50
H21C	−0.5418	0.0244	−0.5632	0.070*	0.50
H21D	−0.5056	−0.0569	−0.5918	0.070*	0.50
H21E	−0.5782	−0.0252	−0.5279	0.070*	0.50
H21F	−0.5421	−0.2375	−0.5498	0.070*	0.50
H42A	−0.0087	−0.1080	−0.6918	0.096*	0.50
H42B	0.1277	−0.1818	−0.6611	0.096*	0.50
H42C	0.0906	0.0411	−0.6585	0.096*	0.50
H42D	0.1484	−0.0578	−0.6491	0.096*	0.50
H42E	0.0120	0.0161	−0.6799	0.096*	0.50
H42F	0.0492	−0.2069	−0.6824	0.096*	0.50
H51A	0.3297	−0.1136	−0.3343	0.087*	0.50
H51B	0.1818	−0.1890	−0.3294	0.087*	0.50
H51C	0.2133	0.0351	−0.3226	0.087*	0.50
H51D	0.1535	−0.0648	−0.3232	0.087*	0.50
H51E	0.3014	0.0107	−0.3281	0.087*	0.50
H51F	0.2699	−0.2134	−0.3350	0.087*	0.50
H7	−0.3110	−0.0615	−0.3336	0.040*
H71	−0.0856	0.0365	−0.2692	0.046*
H72	−0.3525	−0.0255	−0.2312	0.042*
H23A	−0.3471	0.5651	−0.2573	0.083*	0.50
H23B	−0.5017	0.5377	−0.2709	0.083*	0.50
H23C	−0.4026	0.5340	−0.3270	0.083*	0.50
H23D	−0.4872	0.5262	−0.3129	0.083*	0.50
H23E	−0.3326	0.5535	−0.2992	0.083*	0.50
H23F	−0.4316	0.5572	−0.2431	0.083*	0.50
H73	−0.1429	0.1279	−0.1503	0.044*
H32A	−0.4872	0.1715	−0.0459	0.155*	0.50
H32B	−0.4812	0.3876	−0.0708	0.155*	0.50
H32C	−0.4121	0.3325	−0.0052	0.155*	0.50
H32D	−0.4332	0.4229	−0.0354	0.155*	0.50
H32E	−0.4391	0.2068	−0.0105	0.155*	0.50
H32F	−0.5082	0.2619	−0.0760	0.155*	0.50
H74	−0.2603	−0.2476	−0.1425	0.046*
H742A	−0.0343	−0.2722	0.0212	0.174*	0.50
H742B	−0.1659	−0.3196	0.0568	0.174*	0.50
H742C	−0.1213	−0.1015	0.0478	0.174*	0.50
H742D	−0.1800	−0.1900	0.0627	0.174*	0.50
H742E	−0.0484	−0.1426	0.0271	0.174*	0.50
H742F	−0.0931	−0.3607	0.0360	0.174*	0.50
H75	−0.0002	−0.1435	−0.1828	0.048*
H751A	−0.0280	−0.4577	−0.1266	0.046*
H751B	−0.0988	−0.5260	−0.1908	0.046*
H753A	0.3088	−0.5113	−0.2322	0.113*	0.50
H753B	0.2583	−0.6813	−0.2769	0.113*	0.50
H753C	0.3270	−0.7299	−0.2108	0.113*	0.50
H753D	0.2873	−0.7703	−0.2477	0.113*	0.50
H753E	0.3378	−0.6003	−0.2030	0.113*	0.50
H753F	0.2691	−0.5517	−0.2691	0.113*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.039 (3)	0.044 (4)	0.036 (3)	0.007 (3)	0.008 (3)	0.003 (4)
O1	0.057 (2)	0.061 (3)	0.027 (2)	0.002 (2)	0.0045 (18)	0.001 (2)
N2	0.027 (2)	0.050 (3)	0.034 (3)	−0.006 (2)	0.001 (2)	−0.002 (2)
C21	0.045 (4)	0.060 (5)	0.036 (3)	0.004 (3)	0.002 (3)	−0.001 (3)
C3	0.034 (3)	0.029 (4)	0.038 (3)	−0.001 (3)	0.012 (3)	−0.007 (3)
O3	0.034 (2)	0.053 (3)	0.037 (2)	0.0008 (19)	0.0080 (17)	−0.002 (2)
C4	0.028 (3)	0.035 (3)	0.037 (3)	−0.009 (3)	0.011 (2)	−0.014 (3)
C41	0.026 (3)	0.030 (3)	0.063 (4)	−0.008 (3)	0.014 (3)	−0.007 (4)
C42	0.064 (4)	0.105 (6)	0.025 (3)	−0.007 (4)	0.023 (3)	−0.002 (4)
C5	0.035 (3)	0.031 (3)	0.034 (3)	−0.010 (3)	0.004 (2)	0.008 (3)
S5	0.0282 (7)	0.0548 (10)	0.0442 (9)	−0.0012 (8)	0.0065 (6)	−0.0047 (9)
C51	0.044 (4)	0.085 (6)	0.044 (4)	−0.004 (4)	−0.006 (3)	−0.013 (4)
N6	0.036 (3)	0.048 (3)	0.028 (2)	−0.001 (2)	0.0076 (19)	0.000 (3)
C7	0.036 (3)	0.026 (3)	0.039 (3)	0.002 (3)	0.008 (3)	0.005 (3)
N7	0.032 (2)	0.041 (3)	0.029 (2)	0.006 (2)	0.0089 (19)	0.003 (3)
O7	0.040 (2)	0.046 (3)	0.028 (2)	−0.0024 (19)	0.0032 (17)	−0.0031 (19)
C71	0.034 (3)	0.048 (4)	0.033 (3)	0.005 (3)	0.004 (2)	0.006 (3)
C72	0.030 (3)	0.036 (3)	0.040 (4)	−0.005 (3)	0.013 (3)	−0.004 (3)
O721	0.032 (2)	0.042 (3)	0.041 (2)	−0.0008 (18)	0.0054 (18)	−0.006 (2)
C721	0.025 (3)	0.059 (5)	0.047 (4)	0.012 (3)	0.003 (3)	−0.007 (3)
C722	0.051 (4)	0.051 (5)	0.064 (5)	0.003 (3)	0.007 (3)	0.008 (3)
O722	0.039 (2)	0.058 (3)	0.053 (3)	0.002 (2)	0.001 (2)	−0.008 (2)
C73	0.027 (3)	0.045 (4)	0.037 (4)	−0.002 (3)	0.004 (3)	−0.009 (3)
O731	0.036 (2)	0.063 (3)	0.041 (2)	−0.0032 (19)	0.0154 (19)	−0.013 (2)
C731	0.071 (5)	0.057 (5)	0.052 (5)	−0.010 (4)	0.031 (4)	−0.018 (4)
C732	0.069 (5)	0.103 (7)	0.143 (8)	−0.023 (5)	0.082 (5)	−0.052 (6)
O732	0.067 (4)	0.119 (5)	0.100 (4)	−0.039 (3)	0.028 (3)	−0.061 (4)
C74	0.038 (3)	0.051 (4)	0.025 (3)	−0.005 (3)	0.008 (3)	0.000 (3)
O741	0.044 (2)	0.076 (3)	0.028 (2)	−0.002 (2)	0.0007 (19)	0.003 (2)
C741	0.065 (5)	0.073 (5)	0.027 (4)	0.007 (4)	0.011 (3)	0.000 (3)
C742	0.124 (7)	0.195 (12)	0.028 (4)	0.006 (7)	−0.011 (4)	0.044 (6)
O742	0.059 (3)	0.109 (4)	0.052 (3)	−0.007 (3)	0.024 (3)	0.015 (3)
C75	0.037 (3)	0.055 (4)	0.028 (3)	0.003 (3)	0.015 (3)	0.002 (3)
C751	0.033 (3)	0.050 (4)	0.033 (3)	0.004 (3)	0.014 (3)	0.001 (3)
O751	0.030 (2)	0.061 (3)	0.062 (3)	0.005 (2)	0.011 (2)	0.001 (2)
C752	0.033 (3)	0.050 (4)	0.059 (4)	−0.005 (4)	0.006 (3)	−0.016 (4)
C753	0.049 (4)	0.090 (6)	0.087 (5)	0.005 (4)	0.017 (4)	−0.024 (5)
O752	0.042 (3)	0.052 (3)	0.073 (3)	−0.003 (2)	0.011 (2)	−0.008 (3)
C8	0.038 (3)	0.026 (3)	0.032 (3)	0.006 (3)	0.012 (2)	−0.012 (3)
C9	0.026 (3)	0.026 (3)	0.034 (3)	−0.006 (3)	0.004 (2)	−0.006 (3)

Geometric parameters (Å, º)

C1—O1	1.192 (5)	O721—C721	1.367 (7)
C1—N2	1.408 (6)	C721—O722	1.219 (7)
C1—C8	1.529 (7)	C721—C722	1.461 (9)
N2—C3	1.388 (6)	C722—H23A	0.9800
N2—C21	1.459 (6)	C722—H23B	0.9800
C21—H21A	0.9800	C722—H23C	0.9800
C21—H21B	0.9800	C722—H23D	0.9800
C21—H21C	0.9800	C722—H23E	0.9800
C21—H21D	0.9800	C722—H23F	0.9800
C21—H21E	0.9800	C73—O731	1.437 (6)
C21—H21F	0.9800	C73—C74	1.500 (8)
C3—O3	1.222 (5)	C73—H73	1.0000
C3—C9	1.453 (7)	O731—C731	1.358 (7)
C4—C8	1.413 (6)	C731—O732	1.194 (7)
C4—C5	1.425 (7)	C731—C732	1.509 (8)
C4—C41	1.497 (7)	C732—H32A	0.9800
O41—C41	1.242 (7)	C732—H32B	0.9800
O41A—C41	1.229 (9)	C732—H32C	0.9800
C41—O42	1.305 (8)	C732—H32D	0.9800
C41—O42A	1.311 (9)	C732—H32E	0.9800
O42—C42	1.442 (7)	C732—H32F	0.9800
O42A—C42	1.473 (9)	C74—O741	1.418 (6)
C42—H42A	0.9800	C74—C75	1.529 (7)
C42—H42B	0.9800	C74—H74	1.0000
C42—H42D	0.9800	O741—C741	1.363 (7)
C42—H42E	0.9800	C741—O742	1.178 (7)
C42—H42F	0.9800	C741—C742	1.515 (9)
C5—N6	1.343 (6)	C742—H742A	0.9800
C5—S5	1.747 (5)	C742—H742B	0.9800
S5—C51	1.800 (6)	C742—H742C	0.9800
C51—H51A	0.9800	C742—H742D	0.9800
C51—H51B	0.9800	C742—H742E	0.9800
C51—H51C	0.9800	C742—H742F	0.9800
C51—H51D	0.9800	C75—C751	1.504 (8)
C51—H51E	0.9800	C75—H75	1.0000
C51—H51F	0.9800	C751—O751	1.448 (6)
N6—C7	1.361 (6)	C751—H751A	0.9900
C7—N7	1.350 (6)	C751—H751B	0.9900
C7—C9	1.364 (6)	O751—C752	1.330 (7)
N7—C71	1.425 (6)	C752—O752	1.188 (7)
N7—H7	0.8800	C752—C753	1.502 (8)
O7—C71	1.413 (7)	C753—H753A	0.9800
O7—C75	1.436 (6)	C753—H753B	0.9800
C71—C72	1.526 (7)	C753—H753C	0.9800
C71—H71	1.0000	C753—H753D	0.9800
C72—O721	1.459 (7)	C753—H753E	0.9800
C72—C73	1.544 (7)	C753—H753F	0.9800
C72—H72	1.0000	C8—C9	1.370 (6)
O1—C1—N2	123.3 (5)	H23A—C722—H23B	109.5
O1—C1—C8	133.0 (5)	C721—C722—H23C	109.5
N2—C1—C8	103.6 (4)	H23A—C722—H23C	109.5
C3—N2—C1	112.6 (4)	H23B—C722—H23C	109.5
C3—N2—C21	125.4 (4)	C721—C722—H23D	109.5
C1—N2—C21	122.0 (4)	H23A—C722—H23D	141.1
N2—C21—H21A	109.5	H23B—C722—H23D	56.3
N2—C21—H21B	109.5	H23C—C722—H23D	56.3
H21A—C21—H21B	109.5	C721—C722—H23E	109.5
N2—C21—H21C	109.5	H23A—C722—H23E	56.3
H21A—C21—H21C	109.5	H23B—C722—H23E	141.1
H21B—C21—H21C	109.5	H23C—C722—H23E	56.3
N2—C21—H21D	109.5	H23D—C722—H23E	109.5
H21A—C21—H21D	141.1	C721—C722—H23F	109.5
H21B—C21—H21D	56.3	H23A—C722—H23F	56.3
H21C—C21—H21D	56.3	H23B—C722—H23F	56.3
N2—C21—H21E	109.5	H23C—C722—H23F	141.1
H21A—C21—H21E	56.3	H23D—C722—H23F	109.5
H21B—C21—H21E	141.1	H23E—C722—H23F	109.5
H21C—C21—H21E	56.3	O731—C73—C74	111.1 (5)
H21D—C21—H21E	109.5	O731—C73—C72	105.4 (4)
N2—C21—H21F	109.5	C74—C73—C72	109.3 (5)
H21A—C21—H21F	56.3	O731—C73—H73	110.3
H21B—C21—H21F	56.3	C74—C73—H73	110.3
H21C—C21—H21F	141.1	C72—C73—H73	110.3
H21D—C21—H21F	109.5	C731—O731—C73	117.4 (4)
H21E—C21—H21F	109.5	O732—C731—O731	123.3 (6)
O3—C3—N2	124.9 (5)	O732—C731—C732	127.0 (7)
O3—C3—C9	128.8 (5)	O731—C731—C732	109.6 (6)
N2—C3—C9	106.3 (4)	C731—C732—H32A	109.5
C8—C4—C5	116.3 (4)	C731—C732—H32B	109.5
C8—C4—C41	122.9 (5)	H32A—C732—H32B	109.5
C5—C4—C41	120.6 (4)	C731—C732—H32C	109.5
O41A—C41—O41	40.1 (8)	H32A—C732—H32C	109.5
O41A—C41—O42	108.3 (9)	H32B—C732—H32C	109.5
O41—C41—O42	124.9 (5)	C731—C732—H32D	109.5
O41A—C41—O42A	121.5 (9)	H32A—C732—H32D	141.1
O41—C41—O42A	115.2 (9)	H32B—C732—H32D	56.3
O42—C41—O42A	30.3 (7)	H32C—C732—H32D	56.3
O41A—C41—C4	122.5 (9)	C731—C732—H32E	109.5
O41—C41—C4	122.0 (5)	H32A—C732—H32E	56.3
O42—C41—C4	113.1 (4)	H32B—C732—H32E	141.1
O42A—C41—C4	114.3 (6)	H32C—C732—H32E	56.3
C41—O42—C42	114.5 (5)	H32D—C732—H32E	109.5
C41—O42A—C42	112.1 (9)	C731—C732—H32F	109.5
O42—C42—O42A	27.1 (7)	H32A—C732—H32F	56.3
O42—C42—H42A	109.5	H32B—C732—H32F	56.3
O42A—C42—H42A	108.6	H32C—C732—H32F	141.1
O42—C42—H42B	109.5	H32D—C732—H32F	109.5
O42A—C42—H42B	131.1	H32E—C732—H32F	109.5
H42A—C42—H42B	109.5	O741—C74—C73	109.6 (5)
O42—C42—H42C	109.5	O741—C74—C75	108.2 (4)
O42A—C42—H42C	85.1	C73—C74—C75	108.4 (5)
H42A—C42—H42C	109.5	O741—C74—H74	110.2
H42B—C42—H42C	109.5	C73—C74—H74	110.2
O42—C42—H42D	109.5	C75—C74—H74	110.2
O42A—C42—H42D	106.0	C741—O741—C74	117.0 (4)
H42A—C42—H42D	141.1	O742—C741—O741	124.2 (6)
H42B—C42—H42D	56.3	O742—C741—C742	125.5 (7)
H42C—C42—H42D	56.3	O741—C741—C742	110.3 (6)
O42—C42—H42E	109.5	C741—C742—H742A	109.5
O42A—C42—H42E	86.3	C741—C742—H742B	109.5
H42A—C42—H42E	56.3	H742A—C742—H742B	109.5
H42B—C42—H42E	141.1	C741—C742—H742C	109.5
H42C—C42—H42E	56.3	H742A—C742—H742C	109.5
H42D—C42—H42E	109.5	H742B—C742—H742C	109.5
O42—C42—H42F	109.5	C741—C742—H742D	109.5
O42A—C42—H42F	132.7	H742A—C742—H742D	141.1
H42A—C42—H42F	56.3	H742B—C742—H742D	56.3
H42B—C42—H42F	56.3	H742C—C742—H742D	56.3
H42C—C42—H42F	141.1	C741—C742—H742E	109.5
H42D—C42—H42F	109.5	H742A—C742—H742E	56.3
H42E—C42—H42F	109.5	H742B—C742—H742E	141.1
N6—C5—C4	123.5 (4)	H742C—C742—H742E	56.3
N6—C5—S5	116.7 (4)	H742D—C742—H742E	109.5
C4—C5—S5	119.8 (4)	C741—C742—H742F	109.5
C5—S5—C51	101.1 (2)	H742A—C742—H742F	56.3
S5—C51—H51A	109.5	H742B—C742—H742F	56.3
S5—C51—H51B	109.5	H742C—C742—H742F	141.1
H51A—C51—H51B	109.5	H742D—C742—H742F	109.5
S5—C51—H51C	109.5	H742E—C742—H742F	109.5
H51A—C51—H51C	109.5	O7—C75—C751	106.8 (5)
H51B—C51—H51C	109.5	O7—C75—C74	107.7 (4)
S5—C51—H51D	109.5	C751—C75—C74	112.5 (4)
H51A—C51—H51D	141.1	O7—C75—H75	109.9
H51B—C51—H51D	56.3	C751—C75—H75	109.9
H51C—C51—H51D	56.3	C74—C75—H75	109.9
S5—C51—H51E	109.5	O751—C751—C75	106.4 (5)
H51A—C51—H51E	56.3	O751—C751—H751A	110.4
H51B—C51—H51E	141.1	C75—C751—H751A	110.4
H51C—C51—H51E	56.3	O751—C751—H751B	110.4
H51D—C51—H51E	109.5	C75—C751—H751B	110.4
S5—C51—H51F	109.5	H751A—C751—H751B	108.6
H51A—C51—H51F	56.3	C752—O751—C751	116.6 (5)
H51B—C51—H51F	56.3	O752—C752—O751	123.5 (6)
H51C—C51—H51F	141.1	O752—C752—C753	124.4 (7)
H51D—C51—H51F	109.5	O751—C752—C753	112.0 (6)
H51E—C51—H51F	109.5	C752—C753—H753A	109.5
C5—N6—C7	118.2 (4)	C752—C753—H753B	109.5
N7—C7—N6	118.0 (4)	H753A—C753—H753B	109.5
N7—C7—C9	121.1 (4)	C752—C753—H753C	109.5
N6—C7—C9	120.9 (4)	H753A—C753—H753C	109.5
C7—N7—C71	126.4 (4)	H753B—C753—H753C	109.5
C7—N7—H7	116.8	C752—C753—H753D	109.5
C71—N7—H7	116.8	H753A—C753—H753D	141.1
C71—O7—C75	114.0 (4)	H753B—C753—H753D	56.3
O7—C71—N7	110.0 (5)	H753C—C753—H753D	56.3
O7—C71—C72	107.4 (4)	C752—C753—H753E	109.5
N7—C71—C72	108.9 (4)	H753A—C753—H753E	56.3
O7—C71—H71	110.2	H753B—C753—H753E	141.1
N7—C71—H71	110.2	H753C—C753—H753E	56.3
C72—C71—H71	110.2	H753D—C753—H753E	109.5
O721—C72—C71	110.0 (4)	C752—C753—H753F	109.5
O721—C72—C73	106.3 (4)	H753A—C753—H753F	56.3
C71—C72—C73	112.2 (4)	H753B—C753—H753F	56.3
O721—C72—H72	109.4	H753C—C753—H753F	141.1
C71—C72—H72	109.4	H753D—C753—H753F	109.5
C73—C72—H72	109.4	H753E—C753—H753F	109.5
C721—O721—C72	117.0 (4)	C9—C8—C4	118.4 (4)
O722—C721—O721	121.7 (6)	C9—C8—C1	107.5 (4)
O722—C721—C722	126.5 (6)	C4—C8—C1	134.2 (4)
O721—C721—C722	111.6 (6)	C7—C9—C8	122.5 (4)
C721—C722—H23A	109.5	C7—C9—C3	127.7 (4)
C721—C722—H23B	109.5	C8—C9—C3	109.8 (4)
O1—C1—N2—C3	−172.9 (6)	C72—O721—C721—C722	174.5 (5)
C8—C1—N2—C3	3.3 (6)	O721—C72—C73—O731	67.1 (5)
O1—C1—N2—C21	4.4 (9)	C71—C72—C73—O731	−172.6 (5)
C8—C1—N2—C21	−179.3 (5)	O721—C72—C73—C74	−173.4 (4)
C1—N2—C3—O3	179.7 (5)	C71—C72—C73—C74	−53.1 (6)
C21—N2—C3—O3	2.5 (9)	C74—C73—O731—C731	111.0 (6)
C1—N2—C3—C9	−1.6 (6)	C72—C73—O731—C731	−130.7 (5)
C21—N2—C3—C9	−178.8 (5)	C73—O731—C731—O732	0.3 (10)
C8—C4—C41—O41A	−155.0 (13)	C73—O731—C731—C732	−178.9 (6)
C5—C4—C41—O41A	20.5 (15)	O731—C73—C74—O741	−70.5 (5)
C8—C4—C41—O41	157.2 (7)	C72—C73—C74—O741	173.6 (4)
C5—C4—C41—O41	−27.2 (9)	O731—C73—C74—C75	171.7 (4)
C8—C4—C41—O42	−22.3 (9)	C72—C73—C74—C75	55.8 (5)
C5—C4—C41—O42	153.2 (7)	C73—C74—O741—C741	100.1 (6)
C8—C4—C41—O42A	10.8 (13)	C75—C74—O741—C741	−141.9 (5)
C5—C4—C41—O42A	−173.7 (12)	C74—O741—C741—O742	−5.6 (9)
O41A—C41—O42—C42	−51.3 (12)	C74—O741—C741—C742	175.8 (6)
O41—C41—O42—C42	−10.1 (11)	C71—O7—C75—C751	−171.7 (4)
O42A—C41—O42—C42	70.4 (11)	C71—O7—C75—C74	67.2 (5)
C4—C41—O42—C42	169.5 (6)	O741—C74—C75—O7	179.7 (5)
O41A—C41—O42A—C42	6 (2)	C73—C74—C75—O7	−61.6 (5)
O41—C41—O42A—C42	51.8 (17)	O741—C74—C75—C751	62.2 (6)
O42—C41—O42A—C42	−64.9 (12)	C73—C74—C75—C751	−179.1 (5)
C4—C41—O42A—C42	−159.4 (10)	O7—C75—C751—O751	83.6 (5)
C41—O42—C42—O42A	−68.2 (11)	C74—C75—C751—O751	−158.4 (4)
C41—O42A—C42—O42	65.2 (13)	C75—C751—O751—C752	−166.9 (5)
C8—C4—C5—N6	−5.1 (9)	C751—O751—C752—O752	1.8 (9)
C41—C4—C5—N6	179.1 (5)	C751—O751—C752—C753	179.5 (5)
C8—C4—C5—S5	177.3 (5)	C5—C4—C8—C9	2.4 (9)
C41—C4—C5—S5	1.5 (8)	C41—C4—C8—C9	178.1 (5)
N6—C5—S5—C51	7.0 (6)	C5—C4—C8—C1	−177.4 (6)
C4—C5—S5—C51	−175.2 (5)	C41—C4—C8—C1	−1.7 (11)
C4—C5—N6—C7	3.8 (9)	O1—C1—C8—C9	171.8 (7)
S5—C5—N6—C7	−178.5 (5)	N2—C1—C8—C9	−3.9 (7)
C5—N6—C7—N7	−178.8 (5)	O1—C1—C8—C4	−8.4 (13)
C5—N6—C7—C9	0.2 (9)	N2—C1—C8—C4	175.9 (7)
N6—C7—N7—C71	1.0 (9)	N7—C7—C9—C8	176.2 (5)
C9—C7—N7—C71	−178.0 (6)	N6—C7—C9—C8	−2.7 (9)
C75—O7—C71—N7	179.6 (4)	N7—C7—C9—C3	−6.2 (9)
C75—O7—C71—C72	−62.0 (5)	N6—C7—C9—C3	174.9 (6)
C7—N7—C71—O7	−87.6 (7)	C4—C8—C9—C7	1.3 (9)
C7—N7—C71—C72	154.9 (5)	C1—C8—C9—C7	−178.8 (6)
O7—C71—C72—O721	171.7 (4)	C4—C8—C9—C3	−176.7 (5)
N7—C71—C72—O721	−69.2 (6)	C1—C8—C9—C3	3.2 (7)
O7—C71—C72—C73	53.6 (6)	O3—C3—C9—C7	−0.4 (10)
N7—C71—C72—C73	172.6 (5)	N2—C3—C9—C7	−179.0 (6)
C71—C72—O721—C721	101.7 (5)	O3—C3—C9—C8	177.5 (5)
C73—C72—O721—C721	−136.5 (4)	N2—C3—C9—C8	−1.2 (6)
C72—O721—C721—O722	−1.0 (7)