Arjunglucoside I chloro­methane 0.25-solvate monohydrate

The crystal structure of the title compound (systematic name: β-D-gluco­pyran­osyl 2α,3β,19α,23-tetra­hydroxy­olean-12-en-28-oate chloro­methane 0.25-solvate monohydrate), C₃₆H₅₈O₁₁·0.25CH₃Cl·H₂O, contains a triterpenyl moiety esterified with a gluco­pyran­osyl unit, a disordered mol­ecule of chloro­methane solvent with a partial site occupancy located about a twofold axis and a water mol­ecule of hydration. Three rings of the triterpenyl moiety adopt classical chair conformations, while one ring exhibits an envelope conformation and one has a flattened chair conformation. The gluco­pyran­osyl ring also adopts a chair conformation. The structure is stabilized by extensive intermolecular hydrogen bonds as well as an intramolecular interaction.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in solvent or counterion
• R factor = 0.043
• wR factor = 0.115
• Data-to-parameter ratio = 9.4

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT035_ALERT_1_A No _chemical_absolute_configuration info given .          ?

Author Response: Absolute configuration could not be determined in this analysis.

Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O4     -   H4     ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O12    -   H12A   ...          ?
PLAT432_ALERT_2_B Short Inter X...Y Contact  O4     ..  Cl1     ..       2.85 Ang.

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.70 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.30 Ratio
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      20.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O12    ..  Cl1     ..       3.06 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.40
           From the CIF: _reflns_number_total               4380
           Count of symmetry unique reflns         4430
           Completeness (_total/calc)             98.87%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present          yes

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

β-D-Glucopyranosyl 2α,3β,19α,23-tetrahydroxyolean-12-en-28-oate

Crystal data

C36H58O11·0.25CH3Cl·H2O	F(000) = 1514
Mr = 697.46	Dx = 1.284 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 7564 reflections
a = 30.241 (9) Å	θ = 3.8–27.4°
b = 7.441 (2) Å	µ = 0.11 mm^−1
c = 16.290 (7) Å	T = 293 K
β = 100.103 (12)°	Needle, colorless
V = 3609 (2) Å^3	0.22 × 0.15 × 0.08 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	4380 independent reflections
Radiation source: fine-focus sealed tube	3817 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω and φ scans	θmax = 27.4°, θmin = 3.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −38→38
Tmin = 0.976, Tmax = 0.991	k = −9→9
7564 measured reflections	l = −21→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0635P)^2 + 2.4P] where P = (Fo^2 + 2Fc^2)/3
4380 reflections	(Δ/σ)max = 0.002
467 parameters	Δρmax = 0.38 e Å^−3
4 restraints	Δρmin = −0.38 e Å^−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.32447 (7)	1.2120 (3)	0.22648 (12)	0.0268 (4)
H1	0.3103	1.1917	0.1797	0.040*
O2	0.26369 (6)	0.9381 (3)	0.17554 (11)	0.0261 (4)
H2	0.2743	0.9089	0.1345	0.039*
O3	0.32968 (7)	0.5535 (3)	0.26133 (14)	0.0340 (5)
H3	0.3311	0.4474	0.2484	0.051*
O4	0.52716 (7)	0.8968 (4)	0.69251 (13)	0.0368 (5)
H4	0.5312	0.9675	0.6559	0.055*
O5	0.38323 (6)	0.8399 (3)	0.83006 (12)	0.0250 (4)
O6	0.40705 (6)	0.5564 (3)	0.85895 (12)	0.0250 (4)
O1'	0.36132 (6)	0.5811 (3)	0.95626 (11)	0.0240 (4)
O2'	0.36939 (8)	0.2256 (3)	0.80804 (12)	0.0316 (5)
H2'	0.3783	0.1214	0.8111	0.047*
O3'	0.34410 (7)	0.0305 (3)	0.95509 (13)	0.0295 (5)
H3'	0.3475	−0.0274	0.9138	0.044*
O4'	0.29360 (6)	0.2487 (3)	1.04833 (12)	0.0267 (4)
H4'	0.2693	0.2751	1.0201	0.040*
O6'	0.29510 (7)	0.8015 (3)	1.03761 (12)	0.0272 (4)
H6'	0.3115	0.8663	1.0153	0.041*
C1	0.34176 (9)	1.0996 (4)	0.36681 (16)	0.0221 (5)
H1A	0.3456	1.2203	0.3895	0.027*
H1B	0.3704	1.0611	0.3538	0.027*
C2	0.30683 (9)	1.1031 (4)	0.28667 (16)	0.0215 (5)
H2A	0.2789	1.1564	0.2981	0.026*
C3	0.29726 (9)	0.9187 (4)	0.24924 (16)	0.0203 (5)
H3A	0.3248	0.8742	0.2322	0.024*
C4	0.28277 (9)	0.7812 (4)	0.30974 (16)	0.0219 (5)
C5	0.31848 (8)	0.7862 (4)	0.39137 (16)	0.0203 (5)
H5	0.3467	0.7517	0.3739	0.024*
C6	0.31069 (10)	0.6421 (4)	0.45403 (17)	0.0258 (6)
H6A	0.3023	0.5302	0.4250	0.031*
H6B	0.2862	0.6785	0.4817	0.031*
C7	0.35300 (9)	0.6136 (4)	0.51871 (17)	0.0240 (6)
H7A	0.3767	0.5690	0.4911	0.029*
H7B	0.3471	0.5230	0.5582	0.029*
C8	0.36910 (8)	0.7873 (4)	0.56638 (15)	0.0188 (5)
C9	0.37046 (9)	0.9453 (4)	0.50441 (16)	0.0193 (5)
H9	0.3950	0.9149	0.4748	0.023*
C10	0.32827 (9)	0.9720 (4)	0.43360 (16)	0.0201 (5)
C11	0.38632 (10)	1.1182 (4)	0.55348 (18)	0.0271 (6)
H11A	0.4028	1.1913	0.5198	0.033*
H11B	0.3601	1.1861	0.5617	0.033*
C12	0.41555 (9)	1.0880 (4)	0.63720 (17)	0.0243 (6)
H12	0.4240	1.1893	0.6696	0.029*
C13	0.43035 (8)	0.9304 (4)	0.66922 (16)	0.0193 (5)
C14	0.41885 (8)	0.7611 (4)	0.61606 (15)	0.0189 (5)
C15	0.42246 (9)	0.5869 (4)	0.66804 (17)	0.0234 (6)
H15A	0.3946	0.5692	0.6887	0.028*
H15B	0.4261	0.4862	0.6320	0.028*
C16	0.46146 (9)	0.5868 (4)	0.74223 (16)	0.0232 (6)
H16A	0.4897	0.5979	0.7221	0.028*
H16B	0.4618	0.4738	0.7721	0.028*
C17	0.45668 (8)	0.7430 (4)	0.80163 (16)	0.0218 (5)
C18	0.45927 (9)	0.9250 (4)	0.75706 (17)	0.0214 (5)
H18	0.4462	1.0141	0.7902	0.026*
C19	0.50798 (9)	0.9903 (4)	0.75466 (17)	0.0267 (6)
H19	0.5060	1.1173	0.7385	0.032*
C20	0.53991 (10)	0.9790 (5)	0.83957 (18)	0.0340 (7)
C21	0.53850 (10)	0.7880 (5)	0.87362 (19)	0.0357 (7)
H21A	0.5496	0.7052	0.8359	0.043*
H21B	0.5584	0.7807	0.9272	0.043*
C22	0.49154 (9)	0.7311 (5)	0.88406 (17)	0.0294 (6)
H22A	0.4816	0.8070	0.9257	0.035*
H22B	0.4926	0.6083	0.9044	0.035*
C23	0.28451 (10)	0.5970 (4)	0.26932 (18)	0.0285 (6)
H23A	0.2731	0.5066	0.3031	0.034*
H23B	0.2656	0.5972	0.2147	0.034*
C24	0.23390 (9)	0.8112 (5)	0.32055 (18)	0.0324 (7)
H24A	0.2290	0.9368	0.3287	0.049*
H24B	0.2281	0.7449	0.3681	0.049*
H24C	0.2140	0.7704	0.2715	0.049*
C25	0.28795 (9)	1.0536 (4)	0.46610 (17)	0.0275 (6)
H25A	0.2738	0.9627	0.4944	0.041*
H25B	0.2667	1.0996	0.4201	0.041*
H25C	0.2981	1.1496	0.5042	0.041*
C26	0.33623 (9)	0.8262 (4)	0.62768 (17)	0.0236 (6)
H26A	0.3410	0.9463	0.6490	0.035*
H26B	0.3416	0.7422	0.6731	0.035*
H26C	0.3058	0.8143	0.5988	0.035*
C27	0.45337 (9)	0.7415 (4)	0.55651 (16)	0.0248 (6)
H27A	0.4421	0.6582	0.5129	0.037*
H27B	0.4813	0.6979	0.5872	0.037*
H27C	0.4581	0.8564	0.5326	0.037*
C28	0.41150 (9)	0.7237 (4)	0.83013 (15)	0.0206 (5)
C29	0.58797 (11)	1.0233 (7)	0.8281 (2)	0.0508 (10)
H29A	0.5982	0.9336	0.7935	0.076*
H29B	0.6073	1.0250	0.8816	0.076*
H29C	0.5884	1.1389	0.8022	0.076*
C30	0.52571 (13)	1.1189 (6)	0.8991 (2)	0.0463 (9)
H30A	0.5448	1.1093	0.9526	0.069*
H30B	0.4951	1.0978	0.9049	0.069*
H30C	0.5284	1.2372	0.8769	0.069*
C1'	0.36544 (9)	0.4984 (4)	0.88013 (16)	0.0218 (6)
H1'	0.3401	0.5296	0.8362	0.026*
C2'	0.37043 (9)	0.2950 (4)	0.88972 (16)	0.0224 (5)
H2'1	0.3997	0.2680	0.9238	0.027*
C3'	0.33353 (9)	0.2137 (4)	0.93149 (16)	0.0222 (5)
H3'1	0.3049	0.2174	0.8924	0.027*
C4'	0.32883 (9)	0.3179 (4)	1.00981 (16)	0.0212 (5)
H4'1	0.3570	0.3057	1.0495	0.025*
C5'	0.32231 (9)	0.5173 (4)	0.98748 (16)	0.0207 (5)
H5'	0.2957	0.5312	0.9440	0.025*
C6'	0.31739 (10)	0.6348 (4)	1.06081 (17)	0.0263 (6)
H6'1	0.3007	0.5694	1.0968	0.032*
H6'2	0.3470	0.6597	1.0926	0.032*
O12	0.57488 (13)	0.5551 (8)	0.6748 (4)	0.143 (2)
H12A	0.5657	0.4557	0.6579	0.172*
H12B	0.6011	0.5626	0.6684	0.172*
Cl1	0.4622 (2)	0.2036 (11)	0.4067 (4)	0.103 (2)	0.25
C31	0.4881 (5)	0.260 (2)	0.4591 (9)	0.041 (3)*	0.25
H31A	0.4743	0.3491	0.4889	0.062*	0.25
H31B	0.5121	0.3134	0.4363	0.062*	0.25
H31C	0.4997	0.1646	0.4964	0.062*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0364 (11)	0.0209 (10)	0.0226 (9)	−0.0010 (8)	0.0041 (8)	0.0037 (8)
O2	0.0263 (10)	0.0339 (11)	0.0178 (9)	0.0027 (8)	0.0026 (7)	0.0006 (8)
O3	0.0385 (11)	0.0224 (11)	0.0403 (12)	0.0008 (9)	0.0045 (9)	−0.0082 (9)
O4	0.0265 (10)	0.0611 (15)	0.0246 (11)	−0.0062 (11)	0.0095 (9)	0.0006 (10)
O5	0.0277 (10)	0.0224 (10)	0.0272 (10)	0.0017 (8)	0.0107 (8)	0.0022 (8)
O6	0.0229 (9)	0.0235 (10)	0.0316 (10)	0.0004 (8)	0.0129 (8)	0.0056 (9)
O1'	0.0253 (9)	0.0248 (10)	0.0246 (10)	−0.0051 (8)	0.0117 (8)	−0.0024 (8)
O2'	0.0476 (13)	0.0261 (11)	0.0243 (10)	0.0063 (10)	0.0156 (9)	0.0005 (9)
O3'	0.0434 (12)	0.0191 (10)	0.0299 (11)	0.0002 (9)	0.0170 (9)	0.0012 (8)
O4'	0.0266 (10)	0.0309 (11)	0.0245 (9)	−0.0022 (9)	0.0095 (8)	0.0057 (9)
O6'	0.0318 (11)	0.0226 (10)	0.0305 (11)	−0.0012 (8)	0.0146 (9)	−0.0006 (8)
C1	0.0244 (13)	0.0197 (13)	0.0221 (13)	0.0003 (11)	0.0039 (10)	0.0001 (11)
C2	0.0265 (13)	0.0199 (13)	0.0192 (12)	0.0030 (11)	0.0065 (10)	0.0031 (10)
C3	0.0194 (12)	0.0225 (13)	0.0188 (13)	0.0020 (10)	0.0030 (10)	0.0000 (10)
C4	0.0211 (12)	0.0246 (14)	0.0204 (12)	−0.0015 (10)	0.0045 (10)	0.0016 (11)
C5	0.0186 (12)	0.0221 (13)	0.0210 (12)	−0.0015 (10)	0.0056 (10)	0.0002 (11)
C6	0.0288 (14)	0.0255 (14)	0.0225 (13)	−0.0088 (12)	0.0028 (11)	0.0015 (11)
C7	0.0315 (14)	0.0158 (13)	0.0241 (14)	−0.0027 (11)	0.0033 (11)	0.0017 (11)
C8	0.0193 (12)	0.0185 (13)	0.0191 (12)	−0.0006 (10)	0.0044 (9)	0.0008 (10)
C9	0.0214 (12)	0.0161 (12)	0.0205 (13)	−0.0018 (10)	0.0044 (10)	0.0012 (10)
C10	0.0202 (12)	0.0211 (13)	0.0191 (13)	0.0030 (10)	0.0040 (10)	0.0003 (10)
C11	0.0352 (15)	0.0188 (13)	0.0257 (14)	−0.0019 (12)	0.0009 (12)	0.0014 (11)
C12	0.0279 (14)	0.0207 (14)	0.0242 (13)	−0.0050 (11)	0.0043 (11)	−0.0011 (11)
C13	0.0164 (12)	0.0221 (13)	0.0197 (13)	−0.0029 (10)	0.0040 (10)	−0.0005 (11)
C14	0.0183 (12)	0.0196 (13)	0.0193 (12)	0.0009 (10)	0.0047 (9)	0.0024 (10)
C15	0.0270 (13)	0.0188 (13)	0.0244 (14)	0.0017 (11)	0.0044 (11)	0.0003 (11)
C16	0.0234 (13)	0.0263 (14)	0.0213 (13)	0.0044 (11)	0.0074 (10)	0.0051 (11)
C17	0.0180 (12)	0.0271 (14)	0.0207 (12)	−0.0019 (11)	0.0043 (10)	0.0015 (11)
C18	0.0215 (13)	0.0232 (14)	0.0200 (13)	−0.0030 (11)	0.0047 (10)	0.0006 (11)
C19	0.0255 (13)	0.0306 (16)	0.0249 (14)	−0.0081 (11)	0.0065 (11)	0.0038 (12)
C20	0.0257 (15)	0.050 (2)	0.0244 (14)	−0.0119 (14)	0.0006 (12)	0.0026 (14)
C21	0.0243 (14)	0.053 (2)	0.0271 (14)	−0.0027 (14)	−0.0030 (11)	0.0080 (15)
C22	0.0260 (14)	0.0397 (17)	0.0219 (13)	−0.0033 (13)	0.0025 (11)	0.0076 (13)
C23	0.0347 (15)	0.0281 (15)	0.0211 (13)	−0.0085 (12)	0.0006 (11)	−0.0006 (12)
C24	0.0208 (13)	0.052 (2)	0.0238 (13)	−0.0082 (13)	0.0023 (11)	0.0027 (14)
C25	0.0254 (13)	0.0315 (16)	0.0259 (14)	0.0093 (12)	0.0050 (11)	−0.0017 (12)
C26	0.0205 (12)	0.0286 (14)	0.0229 (13)	−0.0012 (11)	0.0065 (10)	0.0001 (11)
C27	0.0222 (13)	0.0302 (15)	0.0227 (12)	0.0044 (12)	0.0058 (10)	0.0001 (12)
C28	0.0235 (13)	0.0225 (13)	0.0163 (12)	−0.0018 (11)	0.0047 (9)	0.0006 (10)
C29	0.0289 (16)	0.081 (3)	0.0398 (19)	−0.0191 (19)	−0.0017 (14)	0.009 (2)
C30	0.052 (2)	0.055 (2)	0.0297 (16)	−0.0183 (18)	0.0016 (15)	−0.0061 (16)
C1'	0.0219 (13)	0.0225 (14)	0.0225 (13)	−0.0011 (10)	0.0085 (10)	0.0025 (11)
C2'	0.0237 (13)	0.0221 (13)	0.0220 (13)	0.0009 (10)	0.0058 (10)	0.0007 (11)
C3'	0.0269 (13)	0.0187 (13)	0.0221 (13)	0.0003 (11)	0.0076 (10)	0.0029 (11)
C4'	0.0226 (13)	0.0214 (13)	0.0206 (12)	−0.0020 (10)	0.0066 (10)	0.0029 (10)
C5'	0.0198 (12)	0.0225 (13)	0.0216 (12)	−0.0004 (10)	0.0082 (10)	0.0004 (10)
C6'	0.0335 (15)	0.0241 (14)	0.0229 (13)	0.0026 (12)	0.0091 (11)	−0.0003 (11)
O12	0.057 (2)	0.211 (6)	0.170 (5)	0.042 (3)	0.045 (3)	0.090 (5)
Cl1	0.081 (4)	0.153 (6)	0.087 (4)	−0.026 (4)	0.050 (3)	−0.054 (4)

Geometric parameters (Å, º)

O1—C2	1.444 (3)	C15—H15A	0.9700
O1—H1	0.8200	C15—H15B	0.9700
O2—C3	1.437 (3)	C16—C17	1.535 (4)
O2—H2	0.8200	C16—H16A	0.9700
O3—C23	1.432 (4)	C16—H16B	0.9700
O3—H3	0.8200	C17—C28	1.525 (3)
O4—C19	1.432 (4)	C17—C18	1.545 (4)
O4—H4	0.8200	C17—C22	1.557 (4)
O5—C28	1.216 (3)	C18—C19	1.558 (4)
O6—C28	1.345 (3)	C18—H18	0.9800
O6—C1'	1.429 (3)	C19—C20	1.544 (4)
O1'—C1'	1.410 (3)	C19—H19	0.9800
O1'—C5'	1.444 (3)	C20—C21	1.529 (5)
O2'—C2'	1.423 (3)	C20—C29	1.533 (4)
O2'—H2'	0.8200	C20—C30	1.534 (5)
O3'—C3'	1.437 (3)	C21—C22	1.520 (4)
O3'—H3'	0.8200	C21—H21A	0.9700
O4'—C4'	1.424 (3)	C21—H21B	0.9700
O4'—H4'	0.8200	C22—H22A	0.9700
O6'—C6'	1.431 (3)	C22—H22B	0.9700
O6'—H6'	0.8200	C23—H23A	0.9700
C1—C2	1.529 (4)	C23—H23B	0.9700
C1—C10	1.552 (4)	C24—H24A	0.9600
C1—H1A	0.9700	C24—H24B	0.9600
C1—H1B	0.9700	C24—H24C	0.9600
C2—C3	1.509 (4)	C25—H25A	0.9600
C2—H2A	0.9800	C25—H25B	0.9600
C3—C4	1.536 (4)	C25—H25C	0.9600
C3—H3A	0.9800	C26—H26A	0.9600
C4—C23	1.526 (4)	C26—H26B	0.9600
C4—C24	1.535 (4)	C26—H26C	0.9600
C4—C5	1.559 (4)	C27—H27A	0.9600
C5—C6	1.527 (4)	C27—H27B	0.9600
C5—C10	1.549 (4)	C27—H27C	0.9600
C5—H5	0.9800	C29—H29A	0.9600
C6—C7	1.523 (4)	C29—H29B	0.9600
C6—H6A	0.9700	C29—H29C	0.9600
C6—H6B	0.9700	C30—H30A	0.9600
C7—C8	1.542 (4)	C30—H30B	0.9600
C7—H7A	0.9700	C30—H30C	0.9600
C7—H7B	0.9700	C1'—C2'	1.526 (4)
C8—C26	1.555 (3)	C1'—H1'	0.9800
C8—C9	1.555 (3)	C2'—C3'	1.530 (4)
C8—C14	1.590 (3)	C2'—H2'1	0.9800
C9—C11	1.546 (4)	C3'—C4'	1.521 (4)
C9—C10	1.575 (4)	C3'—H3'1	0.9800
C9—H9	0.9800	C4'—C5'	1.532 (4)
C10—C25	1.537 (4)	C4'—H4'1	0.9800
C11—C12	1.506 (4)	C5'—C6'	1.508 (4)
C11—H11A	0.9700	C5'—H5'	0.9800
C11—H11B	0.9700	C6'—H6'1	0.9700
C12—C13	1.329 (4)	C6'—H6'2	0.9700
C12—H12	0.9300	O12—H12A	0.82
C13—C14	1.534 (4)	O12—H12B	0.82
C13—C18	1.541 (4)	Cl1—C31	1.131 (14)
C14—C15	1.542 (4)	C31—H31A	0.9600
C14—C27	1.552 (3)	C31—H31B	0.9600
C15—C16	1.534 (4)	C31—H31C	0.9600
C2—O1—H1	109.5	O4—C19—C20	109.9 (2)
C3—O2—H2	109.5	O4—C19—C18	111.6 (2)
C23—O3—H3	109.5	C20—C19—C18	114.0 (2)
C19—O4—H4	109.5	O4—C19—H19	107.0
C28—O6—C1'	120.7 (2)	C20—C19—H19	107.0
C1'—O1'—C5'	111.7 (2)	C18—C19—H19	107.0
C2'—O2'—H2'	109.5	C21—C20—C29	109.3 (3)
C3'—O3'—H3'	109.5	C21—C20—C30	111.9 (3)
C4'—O4'—H4'	109.5	C29—C20—C30	107.9 (3)
C6'—O6'—H6'	109.5	C21—C20—C19	108.8 (3)
C2—C1—C10	112.4 (2)	C29—C20—C19	109.7 (2)
C2—C1—H1A	109.1	C30—C20—C19	109.2 (3)
C10—C1—H1A	109.1	C22—C21—C20	112.7 (3)
C2—C1—H1B	109.1	C22—C21—H21A	109.1
C10—C1—H1B	109.1	C20—C21—H21A	109.1
H1A—C1—H1B	107.8	C22—C21—H21B	109.1
O1—C2—C3	107.7 (2)	C20—C21—H21B	109.1
O1—C2—C1	107.9 (2)	H21A—C21—H21B	107.8
C3—C2—C1	112.6 (2)	C21—C22—C17	113.1 (2)
O1—C2—H2A	109.5	C21—C22—H22A	109.0
C3—C2—H2A	109.5	C17—C22—H22A	109.0
C1—C2—H2A	109.5	C21—C22—H22B	109.0
O2—C3—C2	107.6 (2)	C17—C22—H22B	109.0
O2—C3—C4	111.3 (2)	H22A—C22—H22B	107.8
C2—C3—C4	113.7 (2)	O3—C23—C4	110.4 (2)
O2—C3—H3A	108.0	O3—C23—H23A	109.6
C2—C3—H3A	108.0	C4—C23—H23A	109.6
C4—C3—H3A	108.0	O3—C23—H23B	109.6
C23—C4—C24	106.7 (2)	C4—C23—H23B	109.6
C23—C4—C3	106.6 (2)	H23A—C23—H23B	108.1
C24—C4—C3	111.5 (2)	C4—C24—H24A	109.5
C23—C4—C5	108.5 (2)	C4—C24—H24B	109.5
C24—C4—C5	115.8 (2)	H24A—C24—H24B	109.5
C3—C4—C5	107.4 (2)	C4—C24—H24C	109.5
C6—C5—C10	111.7 (2)	H24A—C24—H24C	109.5
C6—C5—C4	112.9 (2)	H24B—C24—H24C	109.5
C10—C5—C4	116.7 (2)	C10—C25—H25A	109.5
C6—C5—H5	104.7	C10—C25—H25B	109.5
C10—C5—H5	104.7	H25A—C25—H25B	109.5
C4—C5—H5	104.7	C10—C25—H25C	109.5
C5—C6—C7	110.5 (2)	H25A—C25—H25C	109.5
C5—C6—H6A	109.5	H25B—C25—H25C	109.5
C7—C6—H6A	109.5	C8—C26—H26A	109.5
C5—C6—H6B	109.5	C8—C26—H26B	109.5
C7—C6—H6B	109.5	H26A—C26—H26B	109.5
H6A—C6—H6B	108.1	C8—C26—H26C	109.5
C6—C7—C8	112.6 (2)	H26A—C26—H26C	109.5
C6—C7—H7A	109.1	H26B—C26—H26C	109.5
C8—C7—H7A	109.1	C14—C27—H27A	109.5
C6—C7—H7B	109.1	C14—C27—H27B	109.5
C8—C7—H7B	109.1	H27A—C27—H27B	109.5
H7A—C7—H7B	107.8	C14—C27—H27C	109.5
C7—C8—C26	107.4 (2)	H27A—C27—H27C	109.5
C7—C8—C9	110.4 (2)	H27B—C27—H27C	109.5
C26—C8—C9	111.6 (2)	O5—C28—O6	123.0 (2)
C7—C8—C14	109.9 (2)	O5—C28—C17	126.9 (2)
C26—C8—C14	110.5 (2)	O6—C28—C17	110.1 (2)
C9—C8—C14	107.0 (2)	C20—C29—H29A	109.5
C11—C9—C8	109.6 (2)	C20—C29—H29B	109.5
C11—C9—C10	114.3 (2)	H29A—C29—H29B	109.5
C8—C9—C10	117.4 (2)	C20—C29—H29C	109.5
C11—C9—H9	104.7	H29A—C29—H29C	109.5
C8—C9—H9	104.7	H29B—C29—H29C	109.5
C10—C9—H9	104.7	C20—C30—H30A	109.5
C25—C10—C5	113.8 (2)	C20—C30—H30B	109.5
C25—C10—C1	108.8 (2)	H30A—C30—H30B	109.5
C5—C10—C1	106.7 (2)	C20—C30—H30C	109.5
C25—C10—C9	112.8 (2)	H30A—C30—H30C	109.5
C5—C10—C9	106.2 (2)	H30B—C30—H30C	109.5
C1—C10—C9	108.2 (2)	O1'—C1'—O6	107.3 (2)
C12—C11—C9	115.0 (2)	O1'—C1'—C2'	111.4 (2)
C12—C11—H11A	108.5	O6—C1'—C2'	104.4 (2)
C9—C11—H11A	108.5	O1'—C1'—H1'	111.1
C12—C11—H11B	108.5	O6—C1'—H1'	111.1
C9—C11—H11B	108.5	C2'—C1'—H1'	111.1
H11A—C11—H11B	107.5	O2'—C2'—C1'	106.2 (2)
C13—C12—C11	126.2 (2)	O2'—C2'—C3'	112.0 (2)
C13—C12—H12	116.9	C1'—C2'—C3'	111.8 (2)
C11—C12—H12	116.9	O2'—C2'—H2'1	108.9
C12—C13—C14	118.4 (2)	C1'—C2'—H2'1	108.9
C12—C13—C18	119.0 (2)	C3'—C2'—H2'1	108.9
C14—C13—C18	122.6 (2)	O3'—C3'—C4'	108.0 (2)
C13—C14—C15	113.2 (2)	O3'—C3'—C2'	110.4 (2)
C13—C14—C27	108.6 (2)	C4'—C3'—C2'	110.7 (2)
C15—C14—C27	105.9 (2)	O3'—C3'—H3'1	109.2
C13—C14—C8	106.7 (2)	C4'—C3'—H3'1	109.2
C15—C14—C8	110.6 (2)	C2'—C3'—H3'1	109.2
C27—C14—C8	111.9 (2)	O4'—C4'—C3'	111.9 (2)
C16—C15—C14	113.8 (2)	O4'—C4'—C5'	112.3 (2)
C16—C15—H15A	108.8	C3'—C4'—C5'	108.8 (2)
C14—C15—H15A	108.8	O4'—C4'—H4'1	107.9
C16—C15—H15B	108.8	C3'—C4'—H4'1	107.9
C14—C15—H15B	108.8	C5'—C4'—H4'1	107.9
H15A—C15—H15B	107.7	O1'—C5'—C6'	106.8 (2)
C15—C16—C17	110.6 (2)	O1'—C5'—C4'	108.8 (2)
C15—C16—H16A	109.5	C6'—C5'—C4'	113.5 (2)
C17—C16—H16A	109.5	O1'—C5'—H5'	109.2
C15—C16—H16B	109.5	C6'—C5'—H5'	109.2
C17—C16—H16B	109.5	C4'—C5'—H5'	109.2
H16A—C16—H16B	108.1	O6'—C6'—C5'	113.6 (2)
C28—C17—C16	108.0 (2)	O6'—C6'—H6'1	108.8
C28—C17—C18	110.4 (2)	C5'—C6'—H6'1	108.8
C16—C17—C18	110.4 (2)	O6'—C6'—H6'2	108.8
C28—C17—C22	103.8 (2)	C5'—C6'—H6'2	108.8
C16—C17—C22	112.1 (2)	H6'1—C6'—H6'2	107.7
C18—C17—C22	111.9 (2)	H12A—O12—H12B	107.2
C13—C18—C17	113.1 (2)	Cl1—C31—H31A	109.5
C13—C18—C19	110.7 (2)	Cl1—C31—H31B	109.5
C17—C18—C19	114.3 (2)	H31A—C31—H31B	109.5
C13—C18—H18	106.0	Cl1—C31—H31C	109.5
C17—C18—H18	106.0	H31A—C31—H31C	109.5
C19—C18—H18	106.0	H31B—C31—H31C	109.5
C10—C1—C2—O1	−174.8 (2)	C8—C14—C15—C16	−156.8 (2)
C10—C1—C2—C3	−56.1 (3)	C14—C15—C16—C17	59.2 (3)
O1—C2—C3—O2	−62.1 (3)	C15—C16—C17—C28	57.8 (3)
C1—C2—C3—O2	179.1 (2)	C15—C16—C17—C18	−63.0 (3)
O1—C2—C3—C4	174.1 (2)	C15—C16—C17—C22	171.5 (2)
C1—C2—C3—C4	55.3 (3)	C12—C13—C18—C17	154.6 (2)
O2—C3—C4—C23	70.3 (3)	C14—C13—C18—C17	−27.0 (3)
C2—C3—C4—C23	−167.9 (2)	C12—C13—C18—C19	−75.8 (3)
O2—C3—C4—C24	−45.7 (3)	C14—C13—C18—C19	102.7 (3)
C2—C3—C4—C24	76.1 (3)	C28—C17—C18—C13	−73.6 (3)
O2—C3—C4—C5	−173.5 (2)	C16—C17—C18—C13	45.8 (3)
C2—C3—C4—C5	−51.7 (3)	C22—C17—C18—C13	171.3 (2)
C23—C4—C5—C6	−59.4 (3)	C28—C17—C18—C19	158.6 (2)
C24—C4—C5—C6	60.5 (3)	C16—C17—C18—C19	−82.1 (3)
C3—C4—C5—C6	−174.3 (2)	C22—C17—C18—C19	43.5 (3)
C23—C4—C5—C10	169.2 (2)	C13—C18—C19—O4	−51.6 (3)
C24—C4—C5—C10	−70.9 (3)	C17—C18—C19—O4	77.4 (3)
C3—C4—C5—C10	54.3 (3)	C13—C18—C19—C20	−176.8 (2)
C10—C5—C6—C7	−63.8 (3)	C17—C18—C19—C20	−47.8 (3)
C4—C5—C6—C7	162.4 (2)	O4—C19—C20—C21	−72.7 (3)
C5—C6—C7—C8	58.0 (3)	C18—C19—C20—C21	53.3 (3)
C6—C7—C8—C26	73.5 (3)	O4—C19—C20—C29	46.8 (4)
C6—C7—C8—C9	−48.5 (3)	C18—C19—C20—C29	172.9 (3)
C6—C7—C8—C14	−166.3 (2)	O4—C19—C20—C30	164.9 (3)
C7—C8—C9—C11	179.6 (2)	C18—C19—C20—C30	−69.0 (3)
C26—C8—C9—C11	60.2 (3)	C29—C20—C21—C22	−178.1 (3)
C14—C8—C9—C11	−60.8 (3)	C30—C20—C21—C22	62.4 (3)
C7—C8—C9—C10	47.0 (3)	C19—C20—C21—C22	−58.3 (3)
C26—C8—C9—C10	−72.4 (3)	C20—C21—C22—C17	57.2 (4)
C14—C8—C9—C10	166.6 (2)	C28—C17—C22—C21	−167.3 (3)
C6—C5—C10—C25	−67.4 (3)	C16—C17—C22—C21	76.4 (3)
C4—C5—C10—C25	64.5 (3)	C18—C17—C22—C21	−48.2 (4)
C6—C5—C10—C1	172.6 (2)	C24—C4—C23—O3	−176.6 (2)
C4—C5—C10—C1	−55.5 (3)	C3—C4—C23—O3	64.2 (3)
C6—C5—C10—C9	57.4 (3)	C5—C4—C23—O3	−51.2 (3)
C4—C5—C10—C9	−170.7 (2)	C1'—O6—C28—O5	9.2 (4)
C2—C1—C10—C25	−69.5 (3)	C1'—O6—C28—C17	−172.5 (2)
C2—C1—C10—C5	53.7 (3)	C16—C17—C28—O5	−130.7 (3)
C2—C1—C10—C9	167.7 (2)	C18—C17—C28—O5	−9.9 (4)
C11—C9—C10—C25	−55.7 (3)	C22—C17—C28—O5	110.1 (3)
C8—C9—C10—C25	74.7 (3)	C16—C17—C28—O6	51.1 (3)
C11—C9—C10—C5	178.9 (2)	C18—C17—C28—O6	172.0 (2)
C8—C9—C10—C5	−50.7 (3)	C22—C17—C28—O6	−68.0 (3)
C11—C9—C10—C1	64.6 (3)	C5'—O1'—C1'—O6	−174.3 (2)
C8—C9—C10—C1	−165.0 (2)	C5'—O1'—C1'—C2'	−60.6 (3)
C8—C9—C11—C12	26.4 (3)	C28—O6—C1'—O1'	−74.5 (3)
C10—C9—C11—C12	160.6 (2)	C28—O6—C1'—C2'	167.1 (2)
C9—C11—C12—C13	3.9 (4)	O1'—C1'—C2'—O2'	173.9 (2)
C11—C12—C13—C14	2.7 (4)	O6—C1'—C2'—O2'	−70.6 (3)
C11—C12—C13—C18	−178.7 (2)	O1'—C1'—C2'—C3'	51.5 (3)
C12—C13—C14—C15	−159.4 (2)	O6—C1'—C2'—C3'	167.1 (2)
C18—C13—C14—C15	22.1 (3)	O2'—C2'—C3'—O3'	72.8 (3)
C12—C13—C14—C27	83.3 (3)	C1'—C2'—C3'—O3'	−168.2 (2)
C18—C13—C14—C27	−95.2 (3)	O2'—C2'—C3'—C4'	−167.7 (2)
C12—C13—C14—C8	−37.5 (3)	C1'—C2'—C3'—C4'	−48.7 (3)
C18—C13—C14—C8	144.0 (2)	O3'—C3'—C4'—O4'	−61.0 (3)
C7—C8—C14—C13	−173.8 (2)	C2'—C3'—C4'—O4'	178.0 (2)
C26—C8—C14—C13	−55.4 (3)	O3'—C3'—C4'—C5'	174.3 (2)
C9—C8—C14—C13	66.3 (2)	C2'—C3'—C4'—C5'	53.3 (3)
C7—C8—C14—C15	−50.3 (3)	C1'—O1'—C5'—C6'	−171.3 (2)
C26—C8—C14—C15	68.1 (3)	C1'—O1'—C5'—C4'	65.7 (3)
C9—C8—C14—C15	−170.2 (2)	O4'—C4'—C5'—O1'	174.6 (2)
C7—C8—C14—C27	67.5 (3)	C3'—C4'—C5'—O1'	−61.0 (3)
C26—C8—C14—C27	−174.1 (2)	O4'—C4'—C5'—C6'	55.8 (3)
C9—C8—C14—C27	−52.4 (3)	C3'—C4'—C5'—C6'	−179.8 (2)
C13—C14—C15—C16	−37.1 (3)	O1'—C5'—C6'—O6'	82.3 (3)
C27—C14—C15—C16	81.7 (3)	C4'—C5'—C6'—O6'	−157.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4′^i	0.82	2.15	2.901 (3)	152
O1—H1···O2	0.82	2.35	2.772 (3)	113
O2—H2···O6′^ii	0.82	1.97	2.781 (3)	171
O3—H3···O1^iii	0.82	1.79	2.602 (3)	170
O4—H4···Cl1^iv	0.82	2.06	2.848 (7)	161
O2′—H2′···O5^iii	0.82	2.12	2.914 (3)	163
O3′—H3′···O5^iii	0.82	2.13	2.900 (3)	157
O4′—H4′···O6′^v	0.82	2.02	2.827 (3)	169
O6′—H6′···O3′^vi	0.82	1.94	2.758 (3)	174
O12—H12A···Cl1^vii	0.82	2.24	3.056 (12)	171
O12—H12B···O3^vii	0.82	2.20	2.891 (5)	142

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