5-Phenyl-1,3,4-dioxazol-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-D-gluco­pyran­oside

The crystal structure of the title compound, C₂₂H₂₄N₂O₁₀S, has been determined by X-ray diffraction. The molecule contains a sugar ring and a planar substituted heterocyclic ring linked, unusually, by an S atom. The sugar ring is in the normal chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.036
• wR factor = 0.046
• Data-to-parameter ratio = 15.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT162_ALERT_4_C Missing or Zero su (esd) on y-coordinate for ...          S
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ......        C12

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           27.44
           From the CIF: _reflns_number_total               4988
           Count of symmetry unique reflns         2979
           Completeness (_total/calc)            167.44%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2009
           Fraction of Friedel pairs measured     0.674
           Are heavy atom types Z>Si present          yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare, 1994); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1999); molecular graphics: ORTEPIII (Johnson, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

(I)

Crystal data

C22H24N2O10S	F(000) = 532.00
Mr = 508.50	Dx = 1.398 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 3903 reflections
a = 11.50 (2) Å	θ = 3.1–27.5°
b = 7.35 (1) Å	µ = 0.19 mm^−1
c = 14.30 (2) Å	T = 173 K
β = 92.42 (2)°	Block, colorless
V = 1208 (3) Å^3	0.35 × 0.20 × 0.15 mm
Z = 2

Data collection

Rigaku/MSC Mercury CCD diffractometer	4441 reflections with F^2 > 2σ(F^2)
Detector resolution: 14.63 pixels mm^-1	Rint = 0.021
ω scans	θmax = 27.4°
Absorption correction: multi-scan (Jacobson, 1998)	h = −14→14
Tmin = 0.897, Tmax = 0.972	k = −7→9
9357 measured reflections	l = −18→12
4988 independent reflections

Refinement

Refinement on F	w = 1/[σ^2(Fo) + 0.00063|Fo|^2]
R[F^2 > 2σ(F^2)] = 0.036	(Δ/σ)max = 0.003
wR(F^2) = 0.046	Δρmax = 0.22 e Å^−3
S = 1.06	Δρmin = −0.18 e Å^−3
4971 reflections	Absolute structure: Flack (1983)
315 parameters	Absolute structure parameter: 0.028 (6)
H-atom parameters not refined

Special details

Refinement. Refinement using reflections with F² > 0.0 σ(F²). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
S	0.12808 (5)	0.5580	0.80704 (4)	0.0308 (1)
O1	0.2824 (1)	0.3359 (2)	0.73653 (9)	0.0256 (4)
O2	0.3607 (1)	0.0649 (3)	0.60502 (9)	0.0320 (4)
O3	0.5201 (1)	−0.0962 (3)	0.5706 (1)	0.0493 (5)
O4	0.4886 (1)	−0.0149 (2)	0.81296 (9)	0.0251 (4)
O5	0.4128 (1)	−0.2852 (2)	0.7688 (1)	0.0431 (5)
O6	0.2964 (1)	−0.0413 (2)	0.94629 (9)	0.0243 (4)
O7	0.4612 (1)	−0.0495 (2)	1.0375 (1)	0.0364 (4)
O8	0.2028 (1)	0.3082 (2)	0.98238 (9)	0.0245 (4)
O9	0.0112 (1)	0.2438 (3)	0.9617 (1)	0.0380 (4)
O10	0.0380 (1)	0.2569 (2)	0.72297 (10)	0.0267 (4)
N1	−0.0947 (2)	0.4530 (3)	0.7688 (1)	0.0386 (6)
N2	−0.1523 (2)	0.3070 (3)	0.7223 (1)	0.0383 (6)
C1	0.2479 (2)	0.4014 (3)	0.8249 (1)	0.0240 (5)
C2	0.2256 (2)	0.2418 (3)	0.8902 (1)	0.0220 (5)
C3	0.3332 (2)	0.1215 (3)	0.8995 (1)	0.0213 (5)
C4	0.3764 (2)	0.0733 (3)	0.8026 (1)	0.0214 (5)
C5	0.3925 (2)	0.2444 (3)	0.7447 (1)	0.0242 (5)
C6	0.4331 (2)	0.2049 (3)	0.6476 (1)	0.0313 (6)
C7	0.4152 (2)	−0.0831 (3)	0.5713 (1)	0.0346 (6)
C8	0.3300 (2)	−0.2229 (4)	0.5379 (2)	0.0554 (9)
C9	0.4959 (2)	−0.1946 (3)	0.7917 (1)	0.0273 (5)
C10	0.6192 (2)	−0.2570 (4)	0.8016 (2)	0.0379 (6)
C11	0.3665 (2)	−0.1102 (3)	1.0165 (1)	0.0240 (5)
C12	0.3083 (2)	−0.2669 (3)	1.0611 (2)	0.0335 (6)
C13	0.0899 (2)	0.2997 (3)	1.0107 (1)	0.0263 (5)
C14	0.0830 (2)	0.3658 (3)	1.1091 (1)	0.0306 (6)
C15	0.0147 (2)	0.4171 (3)	0.7665 (1)	0.0282 (5)
C16	−0.0718 (2)	0.1952 (3)	0.6979 (1)	0.0266 (5)
C17	−0.0828 (2)	0.0217 (3)	0.6496 (1)	0.0253 (5)
C18	−0.1935 (2)	−0.0379 (4)	0.6192 (1)	0.0329 (6)
C19	−0.2052 (2)	−0.2001 (4)	0.5718 (2)	0.0422 (7)
C20	−0.1091 (2)	−0.3055 (4)	0.5551 (2)	0.0441 (7)
C21	0.0008 (2)	−0.2482 (4)	0.5862 (2)	0.0400 (7)
C22	0.0144 (2)	−0.0844 (3)	0.6334 (1)	0.0322 (6)
H1	0.3128	0.4698	0.8524	0.0288*
H2	0.1598	0.1713	0.8659	0.0264*
H3	0.3941	0.1821	0.9366	0.0256*
H4	0.3212	−0.0072	0.7705	0.0258*
H5	0.4487	0.3230	0.7770	0.0290*
H6	0.5134	0.1640	0.6516	0.0375*
H7	0.4274	0.3146	0.6099	0.0375*
H8	0.2836	−0.2613	0.5895	0.0662*
H9	0.2794	−0.1719	0.4887	0.0662*
H10	0.3712	−0.3268	0.5138	0.0662*
H11	0.6233	−0.3854	0.7865	0.0454*
H12	0.6662	−0.1883	0.7593	0.0454*
H13	0.6482	−0.2379	0.8655	0.0454*
H14	0.2357	−0.2267	1.0864	0.0401*
H15	0.2925	−0.3610	1.0147	0.0401*
H16	0.3588	−0.3151	1.1112	0.0401*
H17	0.1323	0.2909	1.1502	0.0367*
H18	0.1092	0.4911	1.1129	0.0367*
H19	0.0032	0.3584	1.1281	0.0367*
H20	−0.2616	0.0346	0.6314	0.0396*
H21	−0.2819	−0.2408	0.5498	0.0505*
H22	−0.1182	−0.4197	0.5216	0.0526*
H23	0.0683	−0.3230	0.5750	0.0480*
H24	0.0913	−0.0441	0.6548	0.0386*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.0310 (3)	0.0212 (3)	0.0399 (3)	0.0022 (2)	−0.0027 (2)	−0.0015 (2)
O1	0.0269 (7)	0.0265 (8)	0.0234 (7)	0.0022 (6)	0.0011 (5)	0.0012 (6)
O2	0.0279 (7)	0.0428 (9)	0.0253 (7)	0.0070 (7)	0.0009 (5)	−0.0058 (7)
O3	0.0261 (8)	0.057 (1)	0.066 (1)	0.0055 (8)	0.0084 (8)	−0.0167 (9)
O4	0.0186 (7)	0.0261 (8)	0.0306 (7)	−0.0012 (6)	0.0000 (5)	−0.0039 (6)
O5	0.0372 (9)	0.0242 (9)	0.067 (1)	−0.0066 (7)	−0.0029 (8)	0.0003 (8)
O6	0.0232 (7)	0.0252 (8)	0.0244 (7)	−0.0041 (6)	−0.0011 (5)	0.0069 (6)
O7	0.0273 (8)	0.0363 (10)	0.0447 (9)	−0.0013 (7)	−0.0099 (6)	0.0090 (7)
O8	0.0206 (7)	0.0302 (8)	0.0230 (7)	−0.0045 (6)	0.0028 (5)	−0.0034 (6)
O9	0.0244 (7)	0.047 (1)	0.0425 (9)	−0.0080 (7)	0.0032 (6)	−0.0057 (8)
O10	0.0218 (7)	0.0286 (8)	0.0295 (7)	0.0010 (6)	−0.0015 (5)	−0.0013 (6)
N1	0.0292 (10)	0.036 (1)	0.050 (1)	0.0041 (9)	0.0002 (8)	−0.0073 (9)
N2	0.0263 (9)	0.040 (1)	0.049 (1)	0.0022 (9)	−0.0013 (8)	−0.0035 (9)
C1	0.0237 (10)	0.023 (1)	0.0250 (9)	−0.0027 (8)	−0.0007 (7)	−0.0004 (8)
C2	0.0206 (9)	0.024 (1)	0.0215 (9)	−0.0017 (8)	0.0003 (7)	−0.0030 (8)
C3	0.0219 (9)	0.021 (1)	0.0210 (9)	−0.0040 (7)	−0.0022 (7)	0.0030 (7)
C4	0.0189 (8)	0.0206 (10)	0.0246 (9)	−0.0023 (8)	−0.0001 (7)	−0.0023 (8)
C5	0.0214 (9)	0.027 (1)	0.0241 (9)	−0.0037 (8)	0.0006 (7)	−0.0007 (8)
C6	0.032 (1)	0.036 (1)	0.027 (1)	−0.0005 (10)	0.0057 (8)	0.0024 (9)
C7	0.032 (1)	0.046 (2)	0.026 (1)	0.008 (1)	0.0054 (8)	−0.0071 (9)
C8	0.032 (1)	0.070 (2)	0.064 (2)	0.005 (1)	−0.002 (1)	−0.038 (2)
C9	0.029 (1)	0.024 (1)	0.030 (1)	0.0012 (9)	0.0056 (8)	0.0047 (8)
C10	0.031 (1)	0.035 (1)	0.049 (1)	0.0072 (10)	0.0072 (10)	0.006 (1)
C11	0.026 (1)	0.022 (1)	0.0233 (9)	0.0059 (8)	0.0007 (7)	0.0004 (7)
C12	0.035 (1)	0.031 (1)	0.034 (1)	0.0007 (10)	0.0008 (9)	0.0119 (9)
C13	0.0247 (10)	0.022 (1)	0.032 (1)	−0.0016 (8)	0.0058 (8)	0.0037 (8)
C14	0.035 (1)	0.027 (1)	0.030 (1)	−0.0003 (9)	0.0097 (9)	0.0042 (9)
C15	0.030 (1)	0.025 (1)	0.029 (1)	0.0042 (9)	−0.0008 (8)	0.0007 (8)
C16	0.0196 (9)	0.036 (1)	0.0241 (9)	−0.0019 (9)	−0.0029 (7)	0.0048 (8)
C17	0.0233 (9)	0.034 (1)	0.0188 (8)	−0.0016 (8)	−0.0006 (7)	0.0041 (8)
C18	0.024 (1)	0.044 (1)	0.031 (1)	−0.0001 (10)	−0.0025 (8)	0.001 (1)
C19	0.032 (1)	0.053 (2)	0.041 (1)	−0.009 (1)	−0.0048 (10)	−0.008 (1)
C20	0.043 (1)	0.051 (2)	0.039 (1)	−0.008 (1)	0.006 (1)	−0.018 (1)
C21	0.032 (1)	0.042 (1)	0.047 (1)	0.000 (1)	0.0099 (10)	−0.009 (1)
C22	0.0230 (10)	0.041 (1)	0.033 (1)	−0.0049 (9)	0.0026 (8)	−0.0013 (9)

Geometric parameters (Å, º)

S—C1	1.805 (4)	C17—C18	1.398 (4)
S—C15	1.745 (4)	C17—C22	1.390 (4)
O1—C1	1.424 (3)	C18—C19	1.375 (5)
O1—C5	1.434 (4)	C19—C20	1.379 (4)
O2—C6	1.442 (4)	C20—C21	1.387 (4)
O2—C7	1.354 (4)	C21—C22	1.386 (4)
O3—C7	1.211 (3)	C1—H1	0.9694
O4—C4	1.446 (4)	C2—H2	0.9694
O4—C9	1.359 (4)	C3—H3	0.9690
O5—C9	1.199 (3)	C4—H4	0.9691
O6—C3	1.443 (4)	C5—H5	0.9693
O6—C11	1.359 (3)	C6—H6	0.9705
O7—C11	1.203 (3)	C6—H7	0.9706
O8—C2	1.440 (3)	C8—H8	0.9706
O8—C13	1.378 (3)	C8—H9	0.9693
O9—C13	1.194 (3)	C8—H10	0.9697
O10—C15	1.364 (3)	C10—H11	0.9697
O10—C16	1.375 (3)	C10—H12	0.9699
N1—N2	1.413 (4)	C10—H13	0.9696
N1—C15	1.287 (4)	C12—H14	0.9699
N2—C16	1.297 (4)	C12—H15	0.9703
C1—C2	1.528 (4)	C12—H16	0.9700
C2—C3	1.522 (4)	C14—H17	0.9705
C3—C4	1.533 (4)	C14—H18	0.9698
C4—C5	1.521 (4)	C14—H19	0.9695
C5—C6	1.512 (3)	C18—H20	0.9692
C7—C8	1.485 (4)	C19—H21	0.9711
C9—C10	1.491 (4)	C20—H22	0.9699
C11—C12	1.489 (4)	C21—H23	0.9700
C13—C14	1.494 (3)	C22—H24	0.9698
C16—C17	1.453 (4)
S···O8	3.196 (6)	C11···O4	3.358 (6)
S···O9	3.505 (6)	C12···O4^x	3.416 (7)
S···C13	3.520 (6)	C13···S	3.520 (6)
S···C14^i	3.563 (7)	C14···S^vi	3.563 (7)
S···H19^i	2.8518	C14···O9^i	3.135 (6)
O1···O2	2.908 (6)	C15···O9	3.070 (6)
O1···O5^ii	3.187 (6)	C15···C21^ii	3.562 (7)
O1···O10	2.869 (5)	C18···O3^xii	3.365 (6)
O2···O1	2.908 (6)	C18···C8^vii	3.546 (7)
O3···C18^iii	3.365 (6)	C19···O3^xii	3.249 (6)
O3···C19^iii	3.249 (6)	C20···C22^xi	3.592 (7)
O3···C9	3.267 (6)	C21···C15^v	3.562 (7)
O4···C12^iv	3.416 (7)	C22···C20^vii	3.592 (7)
O4···O6	2.986 (5)	C4···H1	3.0950
O4···C11	3.358 (6)	C8···H20^xi	3.0816
O5···O1^v	3.187 (6)	C10···H17^x	2.9325
O5···C1^v	3.110 (6)	C12···H18^v	3.0163
O5···C7	3.192 (6)	C15···H2	2.8051
O6···O4	2.986 (5)	C18···H12^xii	2.8481
O6···O8	2.841 (5)	C22···H22^vii	2.8331
O7···C10^iv	3.309 (7)	H1···O5^ii	2.4719
O8···S	3.196 (6)	H1···C4	3.0950
O8···O6	2.841 (5)	H1···H3	2.5885
O9···C15	3.070 (6)	H1···H5	2.2162
O9···C14^vi	3.135 (6)	H2···O9	2.2975
O9···S	3.505 (6)	H2···O10	2.5087
O10···O1	2.869 (5)	H2···C15	2.8051
O10···C2	3.154 (6)	H3···O7	2.3411
O10···N2	2.219 (5)	H3···H1	2.5885
O2···H4	2.4855	H3···O7^iv	2.5973
O2···H21^vii	2.7555	H4···O2	2.4855
O3···H10^viii	2.6585	H4···O5	2.2995
O3···H21^iii	2.5416	H5···O5^ii	2.9108
O3···H20^iii	2.7925	H5···H1	2.2162
O3···H6	2.2389	H6···O3	2.2389
O3···H7^ix	2.7547	H6···O4	2.6815
O4···H6	2.6815	H7···O3^viii	2.7547
O4···H16^iv	2.5003	H8···O5	2.9139
O5···H1^v	2.4719	H8···H23	2.5171
O5···H5^v	2.9108	H10···O3^ix	2.6585
O5···H8	2.9139	H10···H20^xi	2.5916
O5···H4	2.2995	H12···C18^iii	2.8481
O7···H3^x	2.5973	H13···O8^x	2.7328
O7···H3	2.3411	H13···H17^x	2.5524
O8···H15^ii	2.6738	H14···H18^v	2.5707
O8···H13^iv	2.7328	H14···O9^vi	2.9012
O9···H2	2.2975	H14···N2^vi	2.9472
O9···H14^i	2.9012	H15···O8^v	2.6738
O9···H18^vi	2.5259	H16···O4^x	2.5003
O10···H2	2.5087	H17···N1^vi	2.7819
O10···H24	2.5042	H17···C10^iv	2.9325
N1···O10	2.218 (5)	H17···H13^iv	2.5524
N2···O10	2.219 (5)	H18···C12^ii	3.0163
N1···H17^i	2.7819	H18···H14^ii	2.5707
N2···H20	2.6721	H18···O9^i	2.5259
N2···H14^i	2.9472	H19···S^vi	2.8518
C1···O5^ii	3.110 (6)	H20···O3^xii	2.7925
C2···O10	3.154 (6)	H20···N2	2.6721
C4···C7	3.548 (7)	H20···C8^vii	3.0816
C7···C9	3.350 (6)	H20···H10^vii	2.5916
C7···O5	3.192 (6)	H21···O3^xii	2.5416
C7···C4	3.548 (7)	H21···O2^xi	2.7555
C8···C18^xi	3.546 (7)	H22···C22^xi	2.8331
C9···C7	3.350 (6)	H23···H8	2.5171
C9···O3	3.267 (6)	H24···O10	2.5042
C10···O7^x	3.309 (7)
C1—S—C15	102.93 (10)	C2—C1—H1	107.25
C1—O1—C5	111.37 (13)	O8—C2—H2	109.86
C6—O2—C7	117.12 (15)	C1—C2—H2	109.88
C4—O4—C9	118.44 (16)	C3—C2—H2	109.89
C3—O6—C11	118.37 (15)	O6—C3—H3	110.28
C2—O8—C13	117.65 (14)	C2—C3—H3	110.30
C15—O10—C16	102.00 (15)	C4—C3—H3	110.29
N2—N1—C15	105.76 (19)	O4—C4—H4	109.79
N1—N2—C16	106.4 (2)	C3—C4—H4	109.78
S—C1—O1	109.24 (12)	C5—C4—H4	109.83
S—C1—C2	115.42 (16)	O1—C5—H5	109.14
O1—C1—C2	110.06 (17)	C4—C5—H5	109.11
O8—C2—C1	109.94 (16)	C6—C5—H5	109.06
O8—C2—C3	107.20 (13)	O2—C6—H6	109.56
C1—C2—C3	110.04 (18)	O2—C6—H7	109.51
O6—C3—C2	105.60 (17)	C5—C6—H6	109.60
O6—C3—C4	109.88 (17)	C5—C6—H7	109.54
C2—C3—C4	110.40 (14)	H6—C6—H7	109.38
O4—C4—C3	109.44 (14)	C7—C8—H8	109.46
O4—C4—C5	107.33 (17)	C7—C8—H9	109.49
C3—C4—C5	110.64 (17)	C7—C8—H10	109.49
O1—C5—C4	107.74 (17)	H8—C8—H9	109.38
O1—C5—C6	108.73 (15)	H8—C8—H10	109.50
C4—C5—C6	112.99 (17)	H9—C8—H10	109.51
O2—C6—C5	109.25 (17)	C9—C10—H11	109.46
O2—C7—O3	122.9 (2)	C9—C10—H12	109.47
O2—C7—C8	111.19 (19)	C9—C10—H13	109.44
O3—C7—C8	125.9 (2)	H11—C10—H12	109.52
O4—C9—O5	123.0 (2)	H11—C10—H13	109.43
O4—C9—C10	110.19 (19)	H12—C10—H13	109.50
O5—C9—C10	126.8 (2)	C11—C12—H14	109.49
O6—C11—O7	123.28 (18)	C11—C12—H15	109.45
O6—C11—C12	109.96 (19)	C11—C12—H16	109.45
O7—C11—C12	126.75 (19)	H14—C12—H15	109.45
O8—C13—O9	122.93 (15)	H14—C12—H16	109.49
O8—C13—C14	110.51 (17)	H15—C12—H16	109.49
O9—C13—C14	126.6 (2)	C13—C14—H17	109.45
S—C15—O10	120.37 (16)	C13—C14—H18	109.44
S—C15—N1	125.96 (17)	C13—C14—H19	109.53
O10—C15—N1	113.56 (19)	H17—C14—H18	109.43
O10—C16—N2	112.28 (19)	H17—C14—H19	109.52
O10—C16—C17	118.29 (19)	H18—C14—H19	109.46
N2—C16—C17	129.4 (2)	C17—C18—H20	120.25
C16—C17—C18	118.9 (2)	C19—C18—H20	120.16
C16—C17—C22	121.1 (2)	C18—C19—H21	119.69
C18—C17—C22	120.0 (2)	C20—C19—H21	119.64
C17—C18—C19	119.6 (2)	C19—C20—H22	120.08
C18—C19—C20	120.7 (2)	C21—C20—H22	119.92
C19—C20—C21	120.0 (3)	C20—C21—H23	119.97
C20—C21—C22	120.2 (2)	C22—C21—H23	119.88
C17—C22—C21	119.6 (2)	C17—C22—H24	120.33
S—C1—H1	107.26	C21—C22—H24	120.11
O1—C1—H1	107.26
S—C1—O1—C5	166.9 (1)	N2—C16—C17—C18	3.4 (3)
S—C1—C2—O8	−61.8 (2)	N2—C16—C17—C22	−176.8 (2)
S—C1—C2—C3	−179.7 (1)	C1—O1—C5—C4	66.0 (2)
S—C15—O10—C16	−176.6 (1)	C1—O1—C5—C6	−171.1 (2)
S—C15—N1—N2	175.6 (2)	C1—C2—O8—C13	106.8 (2)
O1—C1—S—C15	68.6 (1)	C1—C2—C3—C4	−50.2 (2)
O1—C1—C2—O8	174.0 (1)	C2—O8—C13—C14	177.4 (2)
O1—C1—C2—C3	56.1 (2)	C2—C1—S—C15	−56.1 (2)
O1—C5—C4—O4	−178.2 (1)	C2—C1—O1—C5	−65.3 (2)
O1—C5—C4—C3	−58.8 (2)	C2—C3—O6—C11	−135.8 (2)
O1—C5—C6—O2	−70.7 (2)	C2—C3—C4—C5	52.4 (2)
O2—C6—C5—C4	49.0 (2)	C3—O6—C11—C12	174.8 (2)
O3—C7—O2—C6	−4.5 (3)	C3—C2—O8—C13	−133.5 (2)
O4—C4—C3—O6	−73.2 (2)	C3—C4—O4—C9	110.7 (2)
O4—C4—C3—C2	170.6 (2)	C3—C4—C5—C6	−179.0 (2)
O4—C4—C5—C6	61.6 (2)	C4—O4—C9—C10	176.8 (2)
O5—C9—O4—C4	−3.4 (3)	C4—C3—O6—C11	105.1 (2)
O6—C3—C2—O8	71.5 (2)	C5—C4—O4—C9	−129.1 (2)
O6—C3—C2—C1	−168.9 (1)	C5—C6—O2—C7	−126.2 (2)
O6—C3—C4—C5	168.6 (1)	C6—O2—C7—C8	174.6 (2)
O7—C11—O6—C3	−5.2 (3)	C15—O10—C16—C17	−179.2 (2)
O8—C2—C3—C4	−169.7 (1)	C15—N1—N2—C16	1.2 (2)
O9—C13—O8—C2	−1.7 (3)	C16—C17—C18—C19	178.7 (2)
O10—C15—S—C1	−25.0 (2)	C16—C17—C22—C21	−179.3 (2)
O10—C15—N1—N2	−0.6 (2)	C17—C18—C19—C20	0.9 (4)
O10—C16—N2—N1	−1.3 (2)	C17—C22—C21—C20	0.3 (3)
O10—C16—C17—C18	−176.5 (2)	C18—C17—C22—C21	0.5 (3)
O10—C16—C17—C22	3.3 (3)	C18—C19—C20—C21	0.0 (4)
N1—N2—C16—C17	178.8 (2)	C19—C18—C17—C22	−1.1 (3)
N1—C15—S—C1	159.0 (2)	C19—C20—C21—C22	−0.6 (4)
N1—C15—O10—C16	−0.1 (2)	C19—C20—C21—C22	−0.6 (4)
N2—C16—O10—C15	0.9 (2)

Symmetry codes: (i) −x, y+1/2, −z+2; (ii) x, y+1, z; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+2; (v) x, y−1, z; (vi) −x, y−1/2, −z+2; (vii) −x, y+1/2, −z+1; (viii) −x+1, y+1/2, −z+1; (ix) −x+1, y−1/2, −z+1; (x) −x+1, y−1/2, −z+2; (xi) −x, y−1/2, −z+1; (xii) x−1, y, z.