Amygdalin trihydrate

Extensive hydrogen bonding is present in the crystal structure of the title compound [systematic name: (R)-1-cyano-1-(phenyl­meth­yl)-β-D-glucopyranos­yl-(1→6)-β-D-glucopyran­oside], C₂₀H₂₇NO₁₁·3H₂O, involving all of the hydr­oxy groups. The water mol­ecules are also involved in the hydrogen bonding; in particular, one of them acts as a bridge between the endocyclic O atoms of the two sugar residues. The overall conformation of the disaccharide is described by the exo-anomeric conformations, φ′′_H = 26° and φ′_H = 38°, together with an antiperiplanar extended conformation of the constituent sugar residues, with ψ′′ = 155°.

Key indicators

• Single-crystal synchrotron study
• T = 110 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.097
• Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.98 Ratio
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.40 Ratio

Author Response: This is probbaly due to the fact that the hydrogens are refined with a riding model.

Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2Y    ..  H3Y     ..       1.84 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT213_ALERT_2_C Atom O2'     has ADP max/min Ratio .............       3.20 prolat
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         15
            O7  -C7  -C8  -N1    172.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         16
            C1  -C7  -C8  -N1     51.00  3.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         29

Alert level G
  ABSMU_01  Radiation type not identified. Calculation of
            _exptl_absorpt_correction_mu not performed.
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           45.94
           From the CIF: _reflns_number_total               5454
           Count of symmetry unique reflns         5630
           Completeness (_total/calc)             96.87%
           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         no

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

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1998); cell refinement: SMART; data reduction: SAINT (Siemens, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PLATON (Spek, 2003).

(R)-1-cyano-1-(phenylmethyl)-β-D-glucopyranosyl-(1→ 6)-β-D– glucopyranoside

Crystal data

C20H33NO14	F(000) = 544
Mr = 511.47	Dx = 1.403 Mg m^−3
Monoclinic, P21	Synchrotron radiation, λ = 0.891 Å
Hall symbol: P 2yb	Cell parameters from 999 reflections
a = 9.4794 (11) Å	θ = 3.0–29.0°
b = 7.9025 (9) Å	µ = 0.12 mm^−1
c = 16.2016 (19) Å	T = 110 K
β = 94.089 (3)°	Plate, colorless
V = 1210.6 (2) Å^3	0.20 × 0.10 × 0.02 mm
Z = 2

Data collection

Bruker SMART 1K area-detector diffractometer	5454 independent reflections
Radiation source: Beamline I711, Maxlab, Lund, Sweden	5010 reflections with I > 2σ(I)
Silicon monochromator	Rint = 0.031
Detector resolution: 10 pixels mm^-1	θmax = 45.9°, θmin = 1.6°
ω scan at different φ and 2θ	h = −15→14
Absorption correction: part of the refinement model (ΔF) (SADABS; Sheldrick, 2002)	k = −10→12
Tmin = 0.98, Tmax = 1.00	l = −16→25
20604 measured reflections

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0714P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
5454 reflections	Δρmax = 0.50 e Å^−3
343 parameters	Δρmin = −0.55 e Å^−3
10 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.051 (3)

Special details

Experimental. Absolute structure known as it is a natural product.

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.88152 (12)	0.31296 (17)	0.87864 (8)	0.0092 (2)
C2	0.99682 (13)	0.40772 (18)	0.85467 (8)	0.0131 (2)
H2	0.9819	0.4974	0.8160	0.016*
C3	1.13334 (13)	0.3706 (2)	0.88753 (9)	0.0157 (3)
H3	1.2111	0.4362	0.8719	0.019*
C4	1.15560 (13)	0.2378 (2)	0.94307 (10)	0.0197 (3)
H4	1.2485	0.2133	0.9658	0.024*
C5	1.04178 (15)	0.1403 (2)	0.96545 (10)	0.0222 (3)
H5	1.0575	0.0479	1.0025	0.027*
C6	0.90413 (14)	0.1785 (2)	0.93345 (9)	0.0158 (3)
H6	0.8265	0.1127	0.9491	0.019*
C7	0.73589 (13)	0.36194 (19)	0.84184 (8)	0.0125 (2)
H7	0.7257	0.4875	0.8464	0.015*
O7	0.72755 (9)	0.31791 (13)	0.75585 (6)	0.01039 (17)
C8	0.62104 (14)	0.2806 (3)	0.88613 (10)	0.0224 (3)
N1	0.53625 (15)	0.2211 (3)	0.92442 (12)	0.0389 (5)
C1'	0.64769 (11)	0.42740 (15)	0.70300 (7)	0.00656 (19)
H1'	0.6616	0.5476	0.7211	0.008*
C2'	0.69827 (10)	0.40125 (15)	0.61680 (7)	0.00594 (19)
H2'	0.7008	0.2770	0.6052	0.007*
O2'	0.83810 (8)	0.46652 (13)	0.61580 (6)	0.01042 (18)
H2X	0.8909	0.3929	0.5968	0.016*
C3'	0.60074 (10)	0.48632 (15)	0.54979 (7)	0.00522 (18)
H3'	0.6207	0.6106	0.5493	0.006*
O3'	0.63560 (9)	0.41348 (12)	0.47284 (6)	0.00866 (16)
H3X	0.5894	0.4624	0.4336	0.013*
C4'	0.44438 (10)	0.45777 (15)	0.56317 (7)	0.00505 (18)
H4'	0.4225	0.3366	0.5499	0.006*
O4'	0.35603 (9)	0.55936 (12)	0.50759 (6)	0.00853 (16)
H4X	0.3594	0.6606	0.5235	0.013*
C5'	0.41182 (11)	0.48762 (15)	0.65324 (7)	0.00556 (18)
H5'	0.4304	0.6086	0.6684	0.007*
O5'	0.50266 (8)	0.37899 (12)	0.70512 (6)	0.00722 (16)
C6'	0.26037 (11)	0.44187 (15)	0.66901 (8)	0.0078 (2)
H6XA	0.2501	0.4326	0.7292	0.009*
H6XB	0.1949	0.5305	0.6462	0.009*
O6'	0.22795 (8)	0.28318 (12)	0.62937 (6)	0.00766 (16)
C1''	0.12150 (10)	0.18916 (15)	0.66312 (7)	0.00554 (18)
H1''	0.0560	0.2653	0.6915	0.007*
C2''	0.04170 (10)	0.09484 (14)	0.59197 (7)	0.00477 (18)
H2''	0.1105	0.0305	0.5600	0.006*
O2''	−0.03409 (8)	0.21247 (12)	0.53828 (6)	0.00786 (16)
H2Y	0.0218	0.2577	0.5069	0.012*
C3''	−0.06282 (10)	−0.02798 (14)	0.62669 (7)	0.00450 (18)
H3''	−0.1337	0.0371	0.6567	0.005*
O3''	−0.13500 (8)	−0.12627 (12)	0.56258 (6)	0.00721 (15)
H3Y	−0.1399	−0.2274	0.5781	0.011*
C4''	0.01806 (11)	−0.14764 (14)	0.68725 (7)	0.00527 (18)
H4''	0.0898	−0.2115	0.6573	0.006*
O4''	−0.07501 (9)	−0.26505 (12)	0.72259 (6)	0.00915 (16)
H4Y	−0.0967	−0.3420	0.6882	0.014*
C5''	0.09444 (11)	−0.04260 (15)	0.75680 (7)	0.00632 (19)
H5''	0.0229	0.0230	0.7861	0.008*
O5''	0.18930 (8)	0.07326 (12)	0.72073 (6)	0.00724 (16)
C6''	0.18368 (12)	−0.14633 (17)	0.81940 (8)	0.0103 (2)
H6YA	0.2304	−0.0707	0.8617	0.012*
H6YB	0.1227	−0.2262	0.8476	0.012*
O6''	0.28803 (11)	−0.23813 (15)	0.77847 (7)	0.0182 (2)
H62C	0.3464	−0.2812	0.8139	0.027*
OW1	0.51979 (10)	0.50771 (13)	0.31483 (7)	0.01277 (18)
H1W1	0.510 (2)	0.610 (2)	0.3052 (14)	0.019*
H2W1	0.587 (2)	0.476 (3)	0.2876 (13)	0.019*
OW2	0.30569 (13)	0.3800 (2)	0.19742 (9)	0.0294 (3)
H1W2	0.357 (3)	0.432 (4)	0.2304 (15)	0.044*
H2W2	0.238 (2)	0.346 (4)	0.2215 (16)	0.044*
OW3	0.48522 (12)	0.18508 (19)	0.11009 (8)	0.0241 (3)
H1W3	0.429 (2)	0.254 (4)	0.1276 (15)	0.036*
H2W3	0.487 (3)	0.205 (4)	0.0598 (12)	0.036*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0106 (4)	0.0109 (5)	0.0058 (5)	0.0023 (4)	−0.0022 (4)	−0.0005 (4)
C2	0.0157 (5)	0.0137 (6)	0.0097 (6)	−0.0010 (4)	0.0002 (4)	0.0022 (5)
C3	0.0122 (5)	0.0235 (7)	0.0112 (6)	−0.0041 (5)	0.0008 (4)	−0.0021 (5)
C4	0.0107 (4)	0.0328 (8)	0.0149 (7)	0.0050 (5)	−0.0033 (4)	0.0019 (6)
C5	0.0173 (5)	0.0292 (8)	0.0198 (7)	0.0061 (5)	−0.0016 (5)	0.0147 (6)
C6	0.0130 (5)	0.0179 (6)	0.0164 (6)	0.0011 (4)	−0.0003 (4)	0.0088 (5)
C7	0.0117 (4)	0.0179 (6)	0.0076 (5)	0.0052 (4)	−0.0015 (4)	−0.0019 (5)
O7	0.0117 (3)	0.0120 (4)	0.0067 (4)	0.0047 (3)	−0.0046 (3)	−0.0012 (3)
C8	0.0118 (5)	0.0400 (10)	0.0154 (7)	0.0055 (6)	0.0007 (5)	0.0014 (6)
N1	0.0169 (5)	0.0684 (14)	0.0325 (9)	0.0038 (7)	0.0086 (6)	0.0129 (10)
C1'	0.0043 (4)	0.0072 (5)	0.0077 (5)	0.0003 (3)	−0.0026 (3)	−0.0010 (4)
C2'	0.0033 (3)	0.0060 (5)	0.0082 (5)	0.0002 (3)	−0.0015 (3)	−0.0010 (4)
O2'	0.0021 (3)	0.0119 (4)	0.0170 (5)	−0.0011 (3)	−0.0007 (3)	−0.0040 (4)
C3'	0.0038 (3)	0.0051 (4)	0.0067 (5)	−0.0004 (3)	−0.0006 (3)	0.0007 (4)
O3'	0.0083 (3)	0.0122 (4)	0.0056 (4)	0.0023 (3)	0.0009 (3)	0.0006 (3)
C4'	0.0036 (3)	0.0047 (4)	0.0067 (5)	−0.0002 (3)	−0.0013 (3)	0.0005 (4)
O4'	0.0065 (3)	0.0074 (4)	0.0110 (4)	0.0012 (3)	−0.0045 (3)	0.0023 (3)
C5'	0.0039 (3)	0.0043 (4)	0.0085 (5)	−0.0005 (3)	−0.0002 (3)	−0.0010 (4)
O5'	0.0054 (3)	0.0078 (4)	0.0081 (4)	−0.0004 (3)	−0.0019 (3)	0.0012 (3)
C6'	0.0048 (4)	0.0054 (5)	0.0134 (6)	−0.0018 (3)	0.0024 (4)	−0.0032 (4)
O6'	0.0070 (3)	0.0059 (4)	0.0104 (4)	−0.0044 (3)	0.0035 (3)	−0.0029 (3)
C1''	0.0039 (3)	0.0053 (4)	0.0075 (5)	−0.0012 (3)	0.0004 (3)	0.0000 (4)
C2''	0.0031 (3)	0.0049 (4)	0.0061 (5)	−0.0003 (3)	−0.0009 (3)	0.0002 (3)
O2''	0.0050 (3)	0.0083 (4)	0.0102 (4)	0.0007 (3)	−0.0001 (3)	0.0048 (3)
C3''	0.0024 (3)	0.0053 (4)	0.0056 (5)	−0.0007 (3)	−0.0014 (3)	−0.0007 (4)
O3''	0.0066 (3)	0.0060 (4)	0.0085 (4)	−0.0015 (3)	−0.0032 (3)	−0.0015 (3)
C4''	0.0044 (3)	0.0047 (4)	0.0065 (5)	−0.0007 (3)	−0.0009 (3)	0.0005 (4)
O4''	0.0102 (3)	0.0074 (4)	0.0097 (4)	−0.0045 (3)	−0.0005 (3)	0.0020 (3)
C5''	0.0058 (4)	0.0067 (4)	0.0064 (5)	−0.0011 (3)	−0.0002 (3)	0.0002 (4)
O5''	0.0042 (3)	0.0079 (4)	0.0092 (4)	−0.0020 (3)	−0.0026 (3)	0.0018 (3)
C6''	0.0111 (4)	0.0112 (5)	0.0080 (5)	0.0019 (4)	−0.0028 (4)	0.0001 (4)
O6''	0.0180 (4)	0.0221 (6)	0.0132 (5)	0.0130 (4)	−0.0069 (3)	−0.0056 (4)
OW1	0.0103 (4)	0.0129 (4)	0.0153 (5)	0.0006 (3)	0.0025 (3)	0.0023 (4)
OW2	0.0191 (5)	0.0419 (8)	0.0276 (7)	−0.0114 (5)	0.0035 (4)	−0.0059 (6)
OW3	0.0215 (5)	0.0312 (7)	0.0191 (6)	−0.0058 (5)	−0.0030 (4)	−0.0008 (5)

Geometric parameters (Å, º)

C1—C6	1.3915 (19)	C5'—H5'	1.0000
C1—C2	1.4024 (18)	C6'—O6'	1.4322 (15)
C1—C7	1.5145 (17)	C6'—H6XA	0.9900
C2—C3	1.3951 (19)	C6'—H6XB	0.9900
C2—H2	0.9500	O6'—C1''	1.3957 (13)
C3—C4	1.389 (2)	C1''—O5''	1.4275 (14)
C3—H3	0.9500	C1''—C2''	1.5271 (16)
C4—C5	1.394 (2)	C1''—H1''	1.0000
C4—H4	0.9500	C2''—O2''	1.4310 (14)
C5—C6	1.4021 (19)	C2''—C3''	1.5230 (15)
C5—H5	0.9500	C2''—H2''	1.0000
C6—H6	0.9500	O2''—H2Y	0.8400
C7—O7	1.4326 (16)	C3''—O3''	1.4315 (14)
C7—C8	1.492 (2)	C3''—C4''	1.5288 (16)
C7—H7	1.0000	C3''—H3''	1.0000
O7—C1'	1.4009 (14)	O3''—H3Y	0.8400
C8—N1	1.150 (2)	C4''—O4''	1.4280 (14)
C1'—O5'	1.4298 (13)	C4''—C5''	1.5385 (16)
C1'—C2'	1.5227 (16)	C4''—H4''	1.0000
C1'—H1'	1.0000	O4''—H4Y	0.8400
C2'—O2'	1.4235 (13)	C5''—O5''	1.4364 (14)
C2'—C3'	1.5304 (15)	C5''—C6''	1.5145 (17)
C2'—H2'	1.0000	C5''—H5''	1.0000
O2'—H2X	0.8400	C6''—O6''	1.4276 (16)
C3'—O3'	1.4330 (15)	C6''—H6YA	0.9900
C3'—C4'	1.5300 (14)	C6''—H6YB	0.9900
C3'—H3'	1.0000	O6''—H62C	0.8400
O3'—H3X	0.8400	OW1—H1W1	0.824 (18)
C4'—O4'	1.4315 (14)	OW1—H2W1	0.843 (17)
C4'—C5'	1.5311 (17)	OW2—H1W2	0.811 (19)
C4'—H4'	1.0000	OW2—H2W2	0.821 (19)
O4'—H4X	0.8400	OW3—H1W3	0.832 (19)
C5'—O5'	1.4428 (14)	OW3—H2W3	0.832 (19)
C5'—C6'	1.5196 (15)
C6—C1—C2	119.80 (11)	O5'—C5'—H5'	109.8
C6—C1—C7	122.75 (12)	C6'—C5'—H5'	109.8
C2—C1—C7	117.45 (12)	C4'—C5'—H5'	109.8
C3—C2—C1	120.14 (13)	C1'—O5'—C5'	111.22 (9)
C3—C2—H2	119.9	O6'—C6'—C5'	107.94 (9)
C1—C2—H2	119.9	O6'—C6'—H6XA	110.1
C4—C3—C2	120.01 (13)	C5'—C6'—H6XA	110.1
C4—C3—H3	120.0	O6'—C6'—H6XB	110.1
C2—C3—H3	120.0	C5'—C6'—H6XB	110.1
C3—C4—C5	120.08 (12)	H6XA—C6'—H6XB	108.4
C3—C4—H4	120.0	C1''—O6'—C6'	115.37 (9)
C5—C4—H4	120.0	O6'—C1''—O5''	107.06 (8)
C4—C5—C6	120.13 (14)	O6'—C1''—C2''	107.29 (9)
C4—C5—H5	119.9	O5''—C1''—C2''	110.86 (9)
C6—C5—H5	119.9	O6'—C1''—H1''	110.5
C1—C6—C5	119.81 (13)	O5''—C1''—H1''	110.5
C1—C6—H6	120.1	C2''—C1''—H1''	110.5
C5—C6—H6	120.1	O2''—C2''—C3''	109.08 (8)
O7—C7—C8	111.81 (12)	O2''—C2''—C1''	110.00 (9)
O7—C7—C1	107.84 (10)	C3''—C2''—C1''	109.42 (9)
C8—C7—C1	112.12 (12)	O2''—C2''—H2''	109.4
O7—C7—H7	108.3	C3''—C2''—H2''	109.4
C8—C7—H7	108.3	C1''—C2''—H2''	109.4
C1—C7—H7	108.3	C2''—O2''—H2Y	109.5
C1'—O7—C7	115.74 (10)	O3''—C3''—C2''	111.57 (9)
N1—C8—C7	176.11 (19)	O3''—C3''—C4''	108.78 (9)
O7—C1'—O5'	107.38 (10)	C2''—C3''—C4''	108.76 (8)
O7—C1'—C2'	106.57 (9)	O3''—C3''—H3''	109.2
O5'—C1'—C2'	110.60 (9)	C2''—C3''—H3''	109.2
O7—C1'—H1'	110.7	C4''—C3''—H3''	109.2
O5'—C1'—H1'	110.7	C3''—O3''—H3Y	109.5
C2'—C1'—H1'	110.7	O4''—C4''—C3''	111.30 (8)
O2'—C2'—C1'	108.40 (9)	O4''—C4''—C5''	109.19 (9)
O2'—C2'—C3'	110.41 (9)	C3''—C4''—C5''	108.94 (9)
C1'—C2'—C3'	112.17 (9)	O4''—C4''—H4''	109.1
O2'—C2'—H2'	108.6	C3''—C4''—H4''	109.1
C1'—C2'—H2'	108.6	C5''—C4''—H4''	109.1
C3'—C2'—H2'	108.6	C4''—O4''—H4Y	109.5
C2'—O2'—H2X	109.5	O5''—C5''—C6''	106.35 (9)
O3'—C3'—C4'	110.48 (9)	O5''—C5''—C4''	108.75 (9)
O3'—C3'—C2'	106.00 (9)	C6''—C5''—C4''	114.18 (10)
C4'—C3'—C2'	112.15 (9)	O5''—C5''—H5''	109.1
O3'—C3'—H3'	109.4	C6''—C5''—H5''	109.1
C4'—C3'—H3'	109.4	C4''—C5''—H5''	109.1
C2'—C3'—H3'	109.4	C1''—O5''—C5''	114.16 (8)
C3'—O3'—H3X	109.5	O6''—C6''—C5''	109.66 (10)
O4'—C4'—C3'	110.94 (9)	O6''—C6''—H6YA	109.7
O4'—C4'—C5'	111.37 (9)	C5''—C6''—H6YA	109.7
C3'—C4'—C5'	112.06 (9)	O6''—C6''—H6YB	109.7
O4'—C4'—H4'	107.4	C5''—C6''—H6YB	109.7
C3'—C4'—H4'	107.4	H6YA—C6''—H6YB	108.2
C5'—C4'—H4'	107.4	C6''—O6''—H62C	109.5
C4'—O4'—H4X	109.5	H1W1—OW1—H2W1	105.6 (19)
O5'—C5'—C6'	107.00 (10)	H1W2—OW2—H2W2	108 (2)
O5'—C5'—C4'	108.12 (9)	H1W3—OW3—H2W3	106 (2)
C6'—C5'—C4'	112.37 (9)
C6—C1—C2—C3	−1.9 (2)	O7—C1'—O5'—C5'	178.97 (9)
C7—C1—C2—C3	178.90 (13)	C2'—C1'—O5'—C5'	−65.13 (12)
C1—C2—C3—C4	1.1 (2)	C6'—C5'—O5'—C1'	−172.28 (9)
C2—C3—C4—C5	0.6 (2)	C4'—C5'—O5'—C1'	66.47 (11)
C3—C4—C5—C6	−1.5 (3)	O5'—C5'—C6'—O6'	−74.07 (12)
C2—C1—C6—C5	1.1 (2)	C4'—C5'—C6'—O6'	44.45 (13)
C7—C1—C6—C5	−179.78 (14)	C5'—C6'—O6'—C1''	154.93 (10)
C4—C5—C6—C1	0.6 (3)	C6'—O6'—C1''—O5''	−94.69 (11)
C6—C1—C7—O7	−109.30 (15)	C6'—O6'—C1''—C2''	146.25 (9)
C2—C1—C7—O7	69.87 (16)	O6'—C1''—C2''—O2''	−67.73 (11)
C6—C1—C7—C8	14.21 (19)	O5''—C1''—C2''—O2''	175.68 (8)
C2—C1—C7—C8	−166.63 (13)	O6'—C1''—C2''—C3''	172.45 (9)
C8—C7—O7—C1'	91.22 (14)	O5''—C1''—C2''—C3''	55.87 (11)
C1—C7—O7—C1'	−145.08 (11)	O2''—C2''—C3''—O3''	62.77 (11)
O7—C7—C8—N1	172 (3)	C1''—C2''—C3''—O3''	−176.85 (8)
C1—C7—C8—N1	51 (3)	O2''—C2''—C3''—C4''	−177.24 (9)
C7—O7—C1'—O5'	−83.22 (12)	C1''—C2''—C3''—C4''	−56.86 (11)
C7—O7—C1'—C2'	158.25 (10)	O3''—C3''—C4''—O4''	−58.91 (12)
O7—C1'—C2'—O2'	−69.25 (11)	C2''—C3''—C4''—O4''	179.39 (9)
O5'—C1'—C2'—O2'	174.35 (9)	O3''—C3''—C4''—C5''	−179.36 (8)
O7—C1'—C2'—C3'	168.59 (9)	C2''—C3''—C4''—C5''	58.93 (11)
O5'—C1'—C2'—C3'	52.19 (12)	O4''—C4''—C5''—O5''	179.14 (9)
O2'—C2'—C3'—O3'	75.00 (11)	C3''—C4''—C5''—O5''	−59.11 (11)
C1'—C2'—C3'—O3'	−163.99 (9)	O4''—C4''—C5''—C6''	60.57 (12)
O2'—C2'—C3'—C4'	−164.35 (9)	C3''—C4''—C5''—C6''	−177.68 (9)
C1'—C2'—C3'—C4'	−43.34 (13)	O6'—C1''—O5''—C5''	−175.61 (9)
O3'—C3'—C4'—O4'	−70.91 (12)	C2''—C1''—O5''—C5''	−58.88 (12)
C2'—C3'—C4'—O4'	171.08 (9)	C6''—C5''—O5''—C1''	−176.51 (9)
O3'—C3'—C4'—C5'	163.92 (9)	C4''—C5''—O5''—C1''	60.09 (12)
C2'—C3'—C4'—C5'	45.90 (13)	O5''—C5''—C6''—O6''	−61.27 (13)
O4'—C4'—C5'—O5'	178.90 (8)	C4''—C5''—C6''—O6''	58.66 (13)
C3'—C4'—C5'—O5'	−56.16 (12)	H1''—C1''—O6'—C6'	25.7
O4'—C4'—C5'—C6'	61.05 (12)	H1'—C1'—O7—C7	37.8
C3'—C4'—C5'—C6'	−174.02 (10)	C1'—O7—C7—H7	−28.1

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2X···O2′′^i	0.84	1.88	2.701 (1)	166
O3′—H3X···OW1	0.84	2.02	2.813 (2)	157
O4′—H4X···O3′^ii	0.84	2.00	2.817 (1)	164
O2′′—H2Y···O3′′^iii	0.84	1.85	2.690 (1)	175
O3′′—H3Y···O4′′	0.84	2.40	2.835 (1)	113
O3′′—H3Y···O2′^iv	0.84	2.51	3.346 (1)	176
O4′′—H4Y···O2′^iv	0.84	1.99	2.823 (1)	174
O6′′—H62C···OW3^v	0.84	1.96	2.774 (1)	162
OW1—H1W1···O5′^ii	0.82 (2)	2.14 (2)	2.958 (2)	173 (2)
OW1—H2W1···O5′′^ii	0.84 (2)	2.26 (2)	2.904 (1)	133 (2)
OW1—H2W1···O6′′^ii	0.84 (2)	2.36 (2)	3.126 (2)	151 (2)
OW2—H1W2···OW1	0.81 (3)	2.07 (3)	2.864 (2)	165 (3)
OW2—H2W2···O4′′^iii	0.82 (2)	2.04 (2)	2.860 (2)	174 (2)
OW3—H1W3···OW2	0.83 (2)	1.95 (2)	2.760 (2)	164 (2)
OW3—H2W3···N1^vi	0.83 (2)	2.28 (2)	3.094 (2)	167 (2)
C5—H5···Cg^vii	0.95	2.71	3.590 (2)	155
C5′′—H5′′···Cg^viii	1.00	2.83	3.640 (2)	138

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