2-N,5′-Di-O-acetyl-2′,3′-O-isopropyl­ideneguanosine monohydrate

Meier, L.; Sá, M.M.; Bortoluzzi, A.J.

doi:10.1107/S1600536807038330

2-N,5'-Di-O-acetyl-2',3'-O-isopropylideneguanosine monohydrate

The asymmetric unit of the title compound, C₁₇H₂₁N₅O₇·H₂O, consists of two organic molecules (A and B) and two molecules of water. Both molecules show R configurations for all their chiral centres, and the furanose and dioxolane rings have envelope and twist conformations, respectively. The conformation of the nucleoside group is anti. The purine groups of the two molecules are almost parallel, with a dihedral angle between their mean planes of 4.90 (2)°. The molecules are stacked in the [010] direction, with alternating A and B molecules. Hydrogen bonds involving water molecules form an infinite one-dimensional chain, also along the crystallographic b axis. Hydrogen bonding between water molecules connects these chains, generating a double-sheet polymeric structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807038330/cf2128sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807038330/cf2128Isup2.hkl Contains datablock I

CCDC reference: 660245

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.050
wR factor = 0.148
Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.50 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C152
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2WB   ..  H121    ..       1.90 Ang.
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H1WB   ...          ?

Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        100 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       1000 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          6
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.95 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.05 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.25 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.44 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O13
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C52
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C130
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C23
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O

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           30.37
           From the CIF: _reflns_number_total               5699
           Count of symmetry unique reflns         5969
           Completeness (_total/calc)             95.48%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4'    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11'   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12'   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13'   = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14'   = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

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

  12 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Nucleosides and synthetically modified analogues participate in a variety of physiological processes (De Clercq & Field, 2006; Santaniello et al., 2005) and are known to self-associate via hydrogen bonding and base stacking (Shi et al., 2001). In particular, 2',3'-O-isopropylideneguanosine and derivatives are notable for their propensity to aggregate (Shi et al., 2003; Mande et al., 1988; Mande et al., 1989). However, the crystal structures of N2-acetylated guanosines have not been reported so far. In continuation of our research on the chemistry of nucleosides (Sá et al., 2002; Leitão et al., 2004), we recently developed a simple and inexpensive method for the synthesis of 2',3'-O-isopropylidene-2-N-5'-O-diacetylguanosine (I) in good yield and high purity (Sá & Meier, 2006). We now report the crystal structure of this compound.

The asymmetric unit consists of two independent molecules of (I) (Fig. 1) and two molecules of water. Distinct intermolecular interactions (Table 2) and different conformational parameters (Table 1) between the independent molecules of (I) lead the asymmetric unit to be greater than expected. A similar feature was also observed in the crystal structure of 2',3'-O-isopropylideneguanosine (II) reported by Mande et al. (1989).

Bond lengths and angles are within the expected ranges (Allen et al., 1987). Both molecules of (I) show R configuration for their chiral centers C1', C2', C3' and C4' in molecule A and C11', C12', C13' and C14' in molecule B. In molecule A the furanose ring adopts envelope conformation on C3' (pucker C3'-exo), where this atom is 0.421 (5) Å out of the least-squares plane defined by the remaining four atoms, with pseudorotation parameters P and τ_m of 20.6 (5)° and 27.6 (2)°. The dioxolane ring is twisted on O2—C2' bond and exhibits C30-exo–O2-endo type pucker with P = 112.7 (4)° and τ_m = 35.6 (2)°. Molecule B also shows the furanose ring as an envelope on C14' (pucker C14'-exo) with P = 233.3 (4)° and τ_m = 30.6 (2)°, where C14' is displaced of 0.431 (5) Å from the mean plane formed by the four other atoms. The dioxolane ring is twisted on C13'—O13 and exhibits C130-exo–O13-endo pucker type with pseudorotation parameters P = 355.8 (5)° and τ_m = 26.3 (2)°. In the N-acetylated groups, the conformation about the C4'—C5' bond is gauche–gauche with Φ_OC = 50.2 (5)° and Φ_OO = -69.7 (4)° for molecule A and about the C14'—C15' bond it is gauche-anti with Φ_OC = -75.4 (4)° and Φ_OO = 168.7 (3)° for molecule B. Similar conformations for these groups found in molecule A were reported for the crystal structure of compound (II) crystallized from Me₂SO by Mande et al. (1988), but they are significantly different from those determined for (II) crystallized from water/acetone (Mande et al., 1989), where in both molecules the furanose rings are C1'-endo, the conformation around C4'—C5' bonds is anti–gauche and the dioxolane ring in molecule A (II) is C9-endo–O3'-exo.

The purine groups are essentially planar, but the deviation from planarity is slightly different in each independent molecule of (I). The r.m.s. deviations of 10 fitted atoms are 0.005 and 0.020 for molecules A and B, respectively. Despite the N—H···O intramolecular hydrogen bond (Table 2), the torsion angles N3—C2—N21—C22 of -179.0 (3)° and N13—C12—N121—C122 of 175.0 (3)° demonstrate that the terminal amide arms deviate distinctly from the correspondent purine mean plane, while the exocyclic O6 and O16 atoms are retained in their respective planes. The conformation of the nucleoside group is anti with torsion angles O1—C1'—N9—C4 of -140.1 (3)° [A] and O11—C11'—N19—C14 of -178.9 (3)° [B]. These values are significantly different from those found in compound (II), with torsion angles of -94.1° (Mande et al., 1988) and 74.1° and 77.5° (Mande et al., 1989).

The purine groups of molecules A and B are almost parallel, with a dihedral angles between their mean planes of 4.90 (2)°. The molecules are stacked in the [010] direction, with intercalated A and B molecules. In addition, a very interesting packing take place through intermolecular interactions (Fig. 2). The water molecule O1W links A molecules and the water molecule O2W links B molecules, forming an infinite chain, also along the crystallographic b axis. The O2W—H2WB···O1W hydrogen bond between water molecules connects the two chains, thus building a double-sheet polymeric structure.

Related literature top

For related literature, see: Allen et al. (1987); De Clercq & Field (2006); Mande et al. (1988, 1989); Sá & Meier (2006); Sá et al. (2002); Santaniello et al. (2005); Shi et al. (2001, 2003); Leitão et al. (2004).

Experimental top

Selective acetylation of 2',3'-O-isopropylideneguanosine employing a combination of acetic anhydride and recyclable 13X molecular sieves under heterogeneous conditions gave (I) in high purity (81% yield) according to the reported method (Sá & Meier, 2006). Slow crystallization from CH₂Cl₂/AcOEt/MeOH/hexane (1:18:2:1) furnished single crystals (mp 397–398 K), allowing structural elucidation by X-ray crystallographic technique. The absolute configuration for (I) was previously assigned based on ¹H– and ¹³C-NMR shifts for the starting 2',3'-O-isopropylideneguanosine and on the homogeneity of the reaction product; in the absence of significant anomalous scattering, Friedel pairs were merged.

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: SET4 in CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The structure of one of the two indpendent molecules of (I) with the labeling scheme. Displacement ellipsoids are shown at the 40% probability level.
	Fig. 2. The structure of one of the two indpendent molecules of (I) with the labeling scheme. Displacement ellipsoids are shown at the 40% probability level.
	Fig. 3. Packing of (I) showing the molecules connected through hydrogen bonds (dashed lines) and stacked along the b axis.

2-N,5'-O-Diacetyl-2',3'-O-isopropylideneguanosine monohydrate top

Crystal data top

C₁₇H₂₁N₅O₇·H₂O	Z = 2
M_r = 425.40	F(000) = 448
Triclinic, P1	D_x = 1.429 Mg m⁻³
Hall symbol: P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.595 (1) Å	Cell parameters from 25 reflections
b = 9.688 (1) Å	θ = 5.1–18.8°
c = 16.301 (1) Å	µ = 0.12 mm⁻¹
α = 72.72 (1)°	T = 293 K
β = 89.68 (1)°	Prismatic, colourless
γ = 83.82 (1)°	0.50 × 0.23 × 0.16 mm
V = 988.34 (19) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.017
Radiation source: fine-focus sealed tube	θ_max = 30.4°, θ_min = 1.3°
Graphite monochromator	h = −9→9
ω/2θ scans	k = −13→13
6620 measured reflections	l = −22→14
5699 independent reflections	3 standard reflections every 200 reflections
4093 reflections with I > 2σ(I)	intensity decay: <1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0786P)² + 0.2093P] where P = (F_o² + 2F_c²)/3
5699 reflections	(Δ/σ)_max < 0.001
557 parameters	Δρ_max = 0.37 e Å⁻³
3 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₇H₂₁N₅O₇·H₂O	γ = 83.82 (1)°
M_r = 425.40	V = 988.34 (19) Å³
Triclinic, P1	Z = 2
a = 6.595 (1) Å	Mo Kα radiation
b = 9.688 (1) Å	µ = 0.12 mm⁻¹
c = 16.301 (1) Å	T = 293 K
α = 72.72 (1)°	0.50 × 0.23 × 0.16 mm
β = 89.68 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.017
6620 measured reflections	3 standard reflections every 200 reflections
5699 independent reflections	intensity decay: <1%
4093 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.050	3 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.37 e Å⁻³
5699 reflections	Δρ_min = −0.24 e Å⁻³
557 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.5489 (4)	0.9264 (3)	0.7783 (2)	0.0340 (6)
C2	0.5637 (5)	0.9965 (3)	0.8396 (2)	0.0330 (6)
N3	0.5925 (4)	0.9319 (3)	0.92166 (18)	0.0333 (5)
C4	0.6092 (5)	0.7851 (3)	0.9397 (2)	0.0308 (6)
C5	0.5969 (5)	0.7023 (3)	0.8842 (2)	0.0315 (6)
C6	0.5635 (4)	0.7744 (3)	0.7943 (2)	0.0326 (6)
O6	0.5481 (4)	0.7239 (3)	0.73424 (16)	0.0429 (6)
N7	0.6223 (4)	0.5549 (3)	0.9301 (2)	0.0379 (6)
C8	0.6499 (6)	0.5519 (4)	1.0101 (2)	0.0396 (7)
H8	0.6718	0.4663	1.0554	0.048*
N9	0.6430 (4)	0.6879 (3)	1.02033 (18)	0.0356 (6)
C1'	0.6706 (5)	0.7256 (3)	1.0993 (2)	0.0378 (7)
H1'	0.7105	0.8243	1.0857	0.045*
C2'	0.4813 (6)	0.7141 (3)	1.1521 (2)	0.0390 (7)
H2'	0.3563	0.7205	1.1183	0.047*
C3'	0.5225 (6)	0.5712 (4)	1.2242 (2)	0.0440 (8)
H3'	0.4681	0.4908	1.2098	0.053*
O1	0.8251 (4)	0.6254 (3)	1.14928 (18)	0.0489 (6)
O2	0.4720 (5)	0.8171 (3)	1.19937 (16)	0.0483 (6)
O3	0.4292 (5)	0.5984 (3)	1.29675 (19)	0.0618 (8)
C4'	0.7534 (6)	0.5496 (4)	1.2324 (2)	0.0451 (8)
H4'	0.7951	0.5973	1.2739	0.054*
C5'	0.8544 (7)	0.3959 (4)	1.2589 (3)	0.0569 (10)
H5'1	1.0008	0.3949	1.2527	0.068*
H5'2	0.8273	0.3479	1.3186	0.068*
N21	0.5468 (5)	1.1468 (3)	0.8130 (2)	0.0399 (6)
C22	0.5137 (6)	1.2358 (4)	0.7312 (3)	0.0465 (8)
O22	0.4858 (6)	1.1924 (3)	0.6696 (2)	0.0707 (10)
C23	0.5148 (8)	1.3962 (4)	0.7225 (3)	0.0566 (10)
H23A	0.5388	1.4077	0.7780	0.085*
H23B	0.3853	1.4477	0.6992	0.085*
H23C	0.6209	1.4345	0.6847	0.085*
C30	0.3801 (7)	0.7531 (4)	1.2793 (3)	0.0522 (9)
C31	0.1567 (9)	0.7868 (7)	1.2703 (4)	0.0769 (14)
H31A	0.1211	0.8896	1.2587	0.115*
H31B	0.0954	0.7361	1.3226	0.115*
H31C	0.1079	0.7564	1.2237	0.115*
C32	0.4768 (12)	0.8041 (8)	1.3469 (4)	0.0900 (19)
H32A	0.4431	0.9072	1.3345	0.135*
H32B	0.6222	0.7819	1.3471	0.135*
H32C	0.4267	0.7556	1.4022	0.135*
O51	0.7718 (5)	0.3217 (3)	1.20395 (19)	0.0544 (7)
C52	0.8204 (8)	0.1780 (5)	1.2249 (3)	0.0665 (12)
O52	0.9266 (10)	0.1129 (5)	1.2856 (4)	0.132 (2)
C53	0.7288 (11)	0.1140 (6)	1.1641 (4)	0.0841 (17)
H53A	0.6539	0.1898	1.1194	0.126*
H53B	0.6381	0.0460	1.1941	0.126*
H53C	0.8348	0.0646	1.1392	0.126*
N11	0.1225 (4)	0.6227 (3)	0.9599 (2)	0.0398 (6)
C12	0.1310 (5)	0.5385 (4)	0.9062 (2)	0.0363 (7)
N13	0.1113 (4)	0.5873 (3)	0.82256 (18)	0.0355 (6)
C14	0.0864 (5)	0.7348 (3)	0.7941 (2)	0.0320 (6)
C15	0.0782 (5)	0.8324 (4)	0.8417 (2)	0.0351 (7)
C16	0.0982 (5)	0.7765 (4)	0.9338 (2)	0.0390 (7)
O16	0.1000 (4)	0.8424 (3)	0.98721 (18)	0.0520 (7)
N17	0.0603 (4)	0.9738 (3)	0.7872 (2)	0.0406 (6)
C18	0.0581 (5)	0.9593 (4)	0.7106 (3)	0.0414 (8)
H18	0.0497	1.0378	0.6608	0.050*
N19	0.0694 (4)	0.8164 (3)	0.70972 (18)	0.0354 (6)
C11'	0.0976 (5)	0.7588 (4)	0.6352 (2)	0.0372 (7)
H11'	0.2361	0.7093	0.6380	0.045*
C12'	−0.0567 (5)	0.6523 (4)	0.6323 (2)	0.0377 (7)
H12'	−0.1515	0.6411	0.6797	0.045*
O11	0.0717 (4)	0.8759 (3)	0.55897 (17)	0.0497 (6)
O12	0.0358 (5)	0.5154 (3)	0.62789 (18)	0.0500 (6)
O13	−0.0623 (6)	0.6514 (4)	0.4896 (2)	0.0706 (10)
C13'	−0.1672 (6)	0.7242 (4)	0.5448 (2)	0.0471 (8)
H13'	−0.3136	0.7144	0.5468	0.057*
C14'	−0.1235 (6)	0.8797 (4)	0.5190 (2)	0.0465 (8)
H14'	−0.1148	0.9166	0.4564	0.056*
C15'	−0.2766 (7)	0.9774 (5)	0.5506 (3)	0.0571 (10)
H15A	−0.3037	0.9310	0.6104	0.069*
H15B	−0.2215	1.0679	0.5465	0.069*
N121	0.1636 (5)	0.3876 (3)	0.9412 (2)	0.0449 (7)
C122	0.2035 (6)	0.3085 (5)	1.0258 (3)	0.0527 (9)
O122	0.2148 (6)	0.3671 (4)	1.0822 (2)	0.0726 (9)
C123	0.2362 (9)	0.1468 (5)	1.0408 (4)	0.0713 (14)
H12A	0.2212	0.1261	0.9873	0.107*
H12B	0.1374	0.1010	1.0802	0.107*
H12C	0.3710	0.1101	1.0647	0.107*
C130	0.0215 (7)	0.5106 (4)	0.5404 (3)	0.0501 (9)
C131	−0.1049 (13)	0.3942 (8)	0.5376 (4)	0.095 (2)
H13A	−0.0414	0.3021	0.5732	0.142*
H13B	−0.1169	0.3913	0.4795	0.142*
H13C	−0.2381	0.4138	0.5584	0.142*
C132	0.2314 (10)	0.4863 (8)	0.5091 (4)	0.0876 (19)
H13D	0.2943	0.3919	0.5415	0.131*
H13E	0.3111	0.5594	0.5163	0.131*
H13F	0.2240	0.4921	0.4493	0.131*
O151	−0.4605 (5)	1.0066 (4)	0.5013 (3)	0.0728 (10)
C152	−0.4991 (9)	1.1363 (6)	0.4447 (4)	0.0708 (13)
O152	−0.3852 (10)	1.2225 (6)	0.4326 (4)	0.137 (2)
C153	−0.7059 (10)	1.1552 (8)	0.4044 (5)	0.103 (2)
H15C	−0.7699	1.0678	0.4272	0.155*
H15D	−0.6945	1.1752	0.3433	0.155*
H15E	−0.7869	1.2349	0.4165	0.155*
O1W	0.6997 (5)	0.2679 (3)	0.9295 (2)	0.0657 (9)
H1WA	0.6671	0.3556	0.9329	0.079*
H1WB	0.7369	0.2105	0.9797	0.079*
O2W	0.0482 (5)	1.2583 (4)	0.8105 (2)	0.0660 (9)
H2WA	0.0698	1.1624	0.8136	0.079*
H2WB	−0.0548	1.2723	0.8414	0.079*
H1	0.530 (8)	0.980 (6)	0.733 (4)	0.064 (15)*
H11	0.138 (7)	0.576 (5)	1.016 (3)	0.055 (13)*
H21	0.580 (6)	1.182 (4)	0.855 (3)	0.030 (9)*
H121	0.143 (7)	0.339 (5)	0.900 (3)	0.048 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0362 (14)	0.0316 (13)	0.0335 (14)	−0.0039 (10)	0.0007 (11)	−0.0084 (11)
C2	0.0310 (15)	0.0286 (14)	0.0392 (17)	−0.0024 (11)	0.0035 (12)	−0.0104 (12)
N3	0.0397 (14)	0.0246 (12)	0.0364 (14)	−0.0035 (10)	0.0030 (11)	−0.0101 (10)
C4	0.0308 (14)	0.0284 (14)	0.0322 (15)	−0.0041 (11)	0.0031 (11)	−0.0073 (12)
C5	0.0302 (14)	0.0261 (13)	0.0400 (17)	−0.0039 (11)	0.0040 (12)	−0.0124 (12)
C6	0.0251 (14)	0.0344 (15)	0.0431 (17)	−0.0075 (11)	0.0077 (12)	−0.0174 (13)
O6	0.0470 (14)	0.0453 (14)	0.0432 (13)	−0.0093 (11)	0.0034 (11)	−0.0221 (11)
N7	0.0407 (15)	0.0271 (13)	0.0470 (16)	−0.0048 (11)	0.0042 (12)	−0.0125 (11)
C8	0.0500 (19)	0.0263 (14)	0.0424 (18)	−0.0051 (13)	0.0020 (14)	−0.0097 (13)
N9	0.0416 (15)	0.0255 (12)	0.0392 (14)	−0.0040 (10)	−0.0011 (11)	−0.0089 (11)
C1'	0.0502 (19)	0.0277 (14)	0.0358 (16)	−0.0042 (13)	−0.0027 (14)	−0.0098 (12)
C2'	0.0484 (19)	0.0326 (16)	0.0369 (16)	−0.0014 (13)	−0.0012 (14)	−0.0129 (13)
C3'	0.057 (2)	0.0300 (15)	0.0421 (18)	−0.0052 (14)	0.0023 (15)	−0.0058 (13)
O1	0.0426 (14)	0.0517 (15)	0.0448 (14)	−0.0016 (11)	−0.0063 (11)	−0.0041 (12)
O2	0.0747 (18)	0.0322 (12)	0.0386 (13)	−0.0031 (11)	0.0055 (12)	−0.0127 (10)
O3	0.085 (2)	0.0449 (15)	0.0465 (16)	0.0003 (14)	0.0218 (15)	−0.0028 (12)
C4'	0.058 (2)	0.0336 (17)	0.0380 (18)	−0.0025 (15)	−0.0061 (15)	−0.0031 (14)
C5'	0.068 (3)	0.0399 (19)	0.057 (2)	0.0066 (18)	−0.020 (2)	−0.0088 (18)
N21	0.0509 (17)	0.0262 (13)	0.0405 (16)	−0.0023 (11)	−0.0030 (13)	−0.0075 (11)
C22	0.059 (2)	0.0296 (16)	0.046 (2)	−0.0009 (15)	0.0001 (16)	−0.0057 (14)
O22	0.116 (3)	0.0435 (16)	0.0472 (17)	−0.0018 (17)	−0.0089 (17)	−0.0079 (13)
C23	0.076 (3)	0.0267 (17)	0.059 (2)	−0.0025 (17)	0.000 (2)	−0.0010 (16)
C30	0.076 (3)	0.0427 (19)	0.0384 (19)	−0.0026 (18)	0.0052 (18)	−0.0136 (15)
C31	0.073 (3)	0.077 (3)	0.074 (3)	0.010 (3)	0.010 (3)	−0.018 (3)
C32	0.124 (5)	0.109 (5)	0.053 (3)	−0.026 (4)	0.006 (3)	−0.042 (3)
O51	0.0637 (17)	0.0370 (13)	0.0571 (17)	0.0050 (12)	−0.0174 (13)	−0.0090 (12)
C52	0.080 (3)	0.042 (2)	0.072 (3)	0.009 (2)	−0.016 (2)	−0.012 (2)
O52	0.190 (5)	0.053 (2)	0.140 (4)	0.045 (3)	−0.102 (4)	−0.030 (2)
C53	0.105 (4)	0.051 (3)	0.096 (4)	−0.009 (3)	−0.027 (3)	−0.020 (3)
N11	0.0390 (15)	0.0443 (16)	0.0367 (16)	−0.0083 (12)	0.0010 (12)	−0.0116 (13)
C12	0.0315 (16)	0.0342 (16)	0.0421 (17)	−0.0051 (12)	0.0006 (13)	−0.0093 (13)
N13	0.0404 (14)	0.0310 (13)	0.0368 (14)	−0.0057 (11)	−0.0001 (11)	−0.0121 (11)
C14	0.0284 (14)	0.0332 (15)	0.0356 (16)	−0.0027 (11)	0.0016 (12)	−0.0124 (12)
C15	0.0287 (15)	0.0352 (16)	0.0442 (18)	−0.0055 (12)	0.0005 (13)	−0.0157 (13)
C16	0.0292 (15)	0.0450 (19)	0.0477 (19)	−0.0066 (13)	0.0014 (13)	−0.0206 (15)
O16	0.0605 (17)	0.0562 (16)	0.0483 (15)	−0.0084 (13)	−0.0015 (13)	−0.0286 (13)
N17	0.0382 (15)	0.0339 (14)	0.0525 (18)	−0.0047 (11)	−0.0045 (13)	−0.0169 (13)
C18	0.0431 (18)	0.0304 (16)	0.049 (2)	−0.0032 (13)	−0.0052 (15)	−0.0090 (14)
N19	0.0372 (14)	0.0308 (13)	0.0381 (14)	−0.0028 (10)	−0.0033 (11)	−0.0103 (11)
C11'	0.0388 (17)	0.0360 (16)	0.0355 (16)	−0.0008 (13)	0.0008 (13)	−0.0099 (13)
C12'	0.0409 (17)	0.0377 (16)	0.0393 (17)	−0.0041 (13)	0.0014 (13)	−0.0188 (14)
O11	0.0519 (15)	0.0558 (16)	0.0373 (13)	−0.0144 (12)	−0.0004 (11)	−0.0048 (11)
O12	0.0701 (18)	0.0383 (13)	0.0432 (14)	0.0071 (12)	−0.0075 (12)	−0.0191 (11)
O13	0.106 (3)	0.0621 (19)	0.0417 (15)	0.0282 (18)	−0.0193 (16)	−0.0249 (14)
C13'	0.049 (2)	0.050 (2)	0.0450 (19)	0.0072 (15)	−0.0116 (16)	−0.0230 (17)
C14'	0.053 (2)	0.049 (2)	0.0337 (17)	0.0011 (16)	−0.0068 (15)	−0.0089 (15)
C15'	0.067 (3)	0.048 (2)	0.054 (2)	0.0102 (19)	−0.016 (2)	−0.0175 (18)
N121	0.0481 (17)	0.0351 (15)	0.0480 (17)	−0.0066 (12)	−0.0029 (13)	−0.0065 (13)
C122	0.053 (2)	0.047 (2)	0.049 (2)	−0.0040 (17)	−0.0011 (17)	−0.0008 (18)
O122	0.096 (3)	0.063 (2)	0.0476 (18)	−0.0009 (18)	−0.0051 (16)	−0.0019 (15)
C123	0.075 (3)	0.048 (2)	0.074 (3)	−0.001 (2)	−0.008 (2)	0.005 (2)
C130	0.072 (3)	0.0396 (18)	0.0404 (19)	0.0042 (17)	−0.0028 (17)	−0.0183 (15)
C131	0.139 (6)	0.091 (4)	0.072 (4)	−0.048 (4)	−0.008 (4)	−0.039 (3)
C132	0.088 (4)	0.105 (5)	0.055 (3)	0.016 (3)	0.017 (3)	−0.011 (3)
O151	0.0605 (19)	0.0502 (18)	0.107 (3)	0.0030 (14)	−0.0225 (19)	−0.0259 (18)
C152	0.075 (3)	0.060 (3)	0.072 (3)	0.006 (2)	−0.017 (3)	−0.016 (2)
O152	0.134 (5)	0.103 (4)	0.130 (5)	−0.037 (4)	−0.036 (4)	0.043 (3)
C153	0.086 (4)	0.105 (5)	0.119 (6)	0.038 (4)	−0.052 (4)	−0.048 (4)
O1W	0.092 (2)	0.0366 (14)	0.074 (2)	−0.0037 (14)	−0.0163 (17)	−0.0247 (14)
O2W	0.071 (2)	0.0555 (18)	0.085 (2)	−0.0057 (15)	0.0044 (17)	−0.0409 (17)

Geometric parameters (Å, º) top

N1—C2	1.373 (4)	N11—H11	0.89 (5)
N1—C6	1.410 (4)	C12—N13	1.306 (5)
N1—H1	0.77 (6)	C12—N121	1.396 (4)
C2—N3	1.303 (4)	N13—C14	1.357 (4)
C2—N21	1.383 (4)	C14—N19	1.366 (4)
N3—C4	1.356 (4)	C14—C15	1.387 (4)
C4—N9	1.374 (4)	C15—N17	1.387 (5)
C4—C5	1.383 (4)	C15—C16	1.437 (5)
C5—N7	1.393 (4)	C16—O16	1.224 (4)
C5—C6	1.431 (5)	N17—C18	1.299 (5)
C6—O6	1.227 (4)	C18—N19	1.383 (4)
N7—C8	1.310 (5)	C18—H18	0.930
C8—N9	1.373 (4)	N19—C11'	1.483 (4)
C8—H8	0.930	C11'—O11	1.408 (4)
N9—C1'	1.455 (4)	C11'—C12'	1.536 (5)
C1'—O1	1.404 (4)	C11'—H11'	0.980
C1'—C2'	1.508 (5)	C12'—O12	1.420 (4)
C1'—H1'	0.980	C12'—C13'	1.536 (5)
C2'—O2	1.427 (4)	C12'—H12'	0.980
C2'—C3'	1.526 (5)	O11—C14'	1.438 (5)
C2'—H2'	0.980	O12—C130	1.445 (5)
C3'—O3	1.410 (5)	O13—C130	1.423 (5)
C3'—C4'	1.516 (6)	O13—C13'	1.432 (5)
C3'—H3'	0.980	C13'—C14'	1.498 (6)
O1—C4'	1.440 (5)	C13'—H13'	0.980
O2—C30	1.429 (5)	C14'—C15'	1.503 (6)
O3—C30	1.441 (5)	C14'—H14'	0.980
C4'—C5'	1.502 (5)	C15'—O151	1.413 (5)
C4'—H4'	0.980	C15'—H15A	0.970
C5'—O51	1.445 (5)	C15'—H15B	0.970
C5'—H5'1	0.970	N121—C122	1.375 (5)
C5'—H5'2	0.970	N121—H121	0.95 (5)
N21—C22	1.360 (5)	C122—O122	1.221 (6)
N21—H21	0.89 (4)	C122—C123	1.503 (7)
C22—O22	1.220 (5)	C123—H12A	0.960
C22—C23	1.518 (5)	C123—H12B	0.960
C23—H23A	0.960	C123—H12C	0.960
C23—H23B	0.960	C130—C131	1.483 (7)
C23—H23C	0.960	C130—C132	1.492 (7)
C30—C31	1.473 (7)	C131—H13A	0.960
C30—C32	1.504 (7)	C131—H13B	0.960
C31—H31A	0.960	C131—H13C	0.960
C31—H31B	0.960	C132—H13D	0.960
C31—H31C	0.960	C132—H13E	0.960
C32—H32A	0.960	C132—H13F	0.960
C32—H32B	0.960	O151—C152	1.319 (6)
C32—H32C	0.960	C152—O152	1.156 (8)
O51—C52	1.334 (5)	C152—C153	1.487 (8)
C52—O52	1.188 (6)	C153—H15C	0.960
C52—C53	1.478 (8)	C153—H15D	0.960
C53—H53A	0.960	C153—H15E	0.960
C53—H53B	0.960	O1W—H1WA	0.8719
C53—H53C	0.960	O1W—H1WB	0.8614
N11—C12	1.359 (5)	O2W—H2WA	0.9113
N11—C16	1.415 (5)	O2W—H2WB	0.8654

C2—N1—C6	125.4 (3)	C12—N11—H11	117 (3)
C2—N1—H1	113 (4)	C16—N11—H11	118 (3)
C6—N1—H1	122 (4)	N13—C12—N11	125.1 (3)
N3—C2—N1	124.9 (3)	N13—C12—N121	115.9 (3)
N3—C2—N21	117.0 (3)	N11—C12—N121	118.9 (3)
N1—C2—N21	118.1 (3)	C12—N13—C14	111.8 (3)
C2—N3—C4	111.5 (3)	N13—C14—N19	125.0 (3)
N3—C4—N9	125.0 (3)	N13—C14—C15	128.6 (3)
N3—C4—C5	129.0 (3)	N19—C14—C15	106.4 (3)
N9—C4—C5	106.0 (3)	N17—C15—C14	110.0 (3)
C4—C5—N7	110.0 (3)	N17—C15—C16	131.2 (3)
C4—C5—C6	119.0 (3)	C14—C15—C16	118.7 (3)
N7—C5—C6	131.0 (3)	O16—C16—N11	120.3 (3)
O6—C6—N1	119.7 (3)	O16—C16—C15	129.4 (3)
O6—C6—C5	130.1 (3)	N11—C16—C15	110.3 (3)
N1—C6—C5	110.2 (3)	C18—N17—C15	104.4 (3)
C8—N7—C5	104.6 (3)	N17—C18—N19	113.9 (3)
N7—C8—N9	113.1 (3)	N17—C18—H18	123.1
N7—C8—H8	123.5	N19—C18—H18	123.1
N9—C8—H8	123.5	C14—N19—C18	105.3 (3)
C8—N9—C4	106.2 (3)	C14—N19—C11'	125.4 (3)
C8—N9—C1'	128.1 (3)	C18—N19—C11'	128.3 (3)
C4—N9—C1'	125.6 (3)	O11—C11'—N19	108.8 (3)
O1—C1'—N9	107.8 (3)	O11—C11'—C12'	108.1 (3)
O1—C1'—C2'	107.0 (3)	N19—C11'—C12'	112.5 (3)
N9—C1'—C2'	112.3 (3)	O11—C11'—H11'	109.1
O1—C1'—H1'	109.9	N19—C11'—H11'	109.1
N9—C1'—H1'	109.9	C12'—C11'—H11'	109.1
C2'—C1'—H1'	109.9	O12—C12'—C13'	105.3 (3)
O2—C2'—C1'	109.5 (3)	O12—C12'—C11'	113.5 (3)
O2—C2'—C3'	101.1 (3)	C13'—C12'—C11'	103.0 (3)
C1'—C2'—C3'	105.4 (3)	O12—C12'—H12'	111.5
O2—C2'—H2'	113.3	C13'—C12'—H12'	111.5
C1'—C2'—H2'	113.3	C11'—C12'—H12'	111.5
C3'—C2'—H2'	113.3	C11'—O11—C14'	109.9 (3)
O3—C3'—C4'	112.9 (3)	C12'—O12—C130	109.2 (3)
O3—C3'—C2'	105.1 (3)	C130—O13—C13'	108.6 (3)
C4'—C3'—C2'	102.7 (3)	O13—C13'—C14'	109.4 (4)
O3—C3'—H3'	111.9	O13—C13'—C12'	103.2 (3)
C4'—C3'—H3'	111.9	C14'—C13'—C12'	105.6 (3)
C2'—C3'—H3'	111.9	O13—C13'—H13'	112.7
C1'—O1—C4'	111.5 (3)	C14'—C13'—H13'	112.7
C2'—O2—C30	107.3 (3)	C12'—C13'—H13'	112.7
C3'—O3—C30	108.8 (3)	O11—C14'—C13'	104.6 (3)
O1—C4'—C5'	108.8 (3)	O11—C14'—C15'	108.5 (3)
O1—C4'—C3'	105.9 (3)	C13'—C14'—C15'	113.5 (4)
C5'—C4'—C3'	117.2 (3)	O11—C14'—H14'	110.0
O1—C4'—H4'	108.2	C13'—C14'—H14'	110.0
C5'—C4'—H4'	108.2	C15'—C14'—H14'	110.0
C3'—C4'—H4'	108.2	O151—C15'—C14'	110.5 (3)
O51—C5'—C4'	107.6 (3)	O151—C15'—H15A	109.6
O51—C5'—H5'1	110.2	C14'—C15'—H15A	109.6
C4'—C5'—H5'1	110.2	O151—C15'—H15B	109.6
O51—C5'—H5'2	110.2	C14'—C15'—H15B	109.6
C4'—C5'—H5'2	110.2	H15A—C15'—H15B	108.1
H5'1—C5'—H5'2	108.5	C122—N121—C12	127.9 (4)
C22—N21—C2	126.9 (3)	C122—N121—H121	120 (3)
C22—N21—H21	121 (2)	C12—N121—H121	112 (3)
C2—N21—H21	112 (2)	O122—C122—N121	121.9 (4)
O22—C22—N21	123.7 (3)	O122—C122—C123	124.2 (4)
O22—C22—C23	122.3 (4)	N121—C122—C123	113.9 (4)
N21—C22—C23	114.0 (3)	C122—C123—H12A	109.5
C22—C23—H23A	109.5	C122—C123—H12B	109.5
C22—C23—H23B	109.5	H12A—C123—H12B	109.5
H23A—C23—H23B	109.5	C122—C123—H12C	109.5
C22—C23—H23C	109.5	H12A—C123—H12C	109.5
H23A—C23—H23C	109.5	H12B—C123—H12C	109.5
H23B—C23—H23C	109.5	O13—C130—O12	106.8 (3)
O2—C30—O3	105.4 (3)	O13—C130—C131	113.2 (5)
O2—C30—C31	110.0 (4)	O12—C130—C131	109.0 (4)
O3—C30—C31	108.3 (4)	O13—C130—C132	106.4 (4)
O2—C30—C32	107.9 (4)	O12—C130—C132	108.9 (4)
O3—C30—C32	110.3 (4)	C131—C130—C132	112.2 (5)
C31—C30—C32	114.6 (5)	C130—C131—H13A	109.5
C30—C31—H31A	109.5	C130—C131—H13B	109.5
C30—C31—H31B	109.5	H13A—C131—H13B	109.5
H31A—C31—H31B	109.5	C130—C131—H13C	109.5
C30—C31—H31C	109.5	H13A—C131—H13C	109.5
H31A—C31—H31C	109.5	H13B—C131—H13C	109.5
H31B—C31—H31C	109.5	C130—C132—H13D	109.5
C30—C32—H32A	109.5	C130—C132—H13E	109.5
C30—C32—H32B	109.5	H13D—C132—H13E	109.5
H32A—C32—H32B	109.5	C130—C132—H13F	109.5
C30—C32—H32C	109.5	H13D—C132—H13F	109.5
H32A—C32—H32C	109.5	H13E—C132—H13F	109.5
H32B—C32—H32C	109.5	C152—O151—C15'	117.6 (4)
C52—O51—C5'	116.9 (3)	O152—C152—O151	122.2 (5)
O52—C52—O51	122.1 (5)	O152—C152—C153	126.6 (6)
O52—C52—C53	125.7 (5)	O151—C152—C153	111.1 (6)
O51—C52—C53	112.2 (4)	C152—C153—H15C	109.5
C52—C53—H53A	109.5	C152—C153—H15D	109.5
C52—C53—H53B	109.5	H15C—C153—H15D	109.5
H53A—C53—H53B	109.5	C152—C153—H15E	109.5
C52—C53—H53C	109.5	H15C—C153—H15E	109.5
H53A—C53—H53C	109.5	H15D—C153—H15E	109.5
H53B—C53—H53C	109.5	H1WA—O1W—H1WB	109.3
C12—N11—C16	125.4 (3)	H2WA—O2W—H2WB	109.5

C6—N1—C2—N3	−0.4 (5)	C16—N11—C12—N13	−2.4 (5)
C6—N1—C2—N21	179.7 (3)	C16—N11—C12—N121	177.5 (3)
N1—C2—N3—C4	0.8 (4)	N11—C12—N13—C14	1.8 (5)
N21—C2—N3—C4	−179.2 (3)	N121—C12—N13—C14	−178.1 (3)
C2—N3—C4—N9	179.0 (3)	C12—N13—C14—N19	177.5 (3)
C2—N3—C4—C5	−0.9 (5)	C12—N13—C14—C15	−0.7 (5)
N3—C4—C5—N7	−179.9 (3)	N13—C14—C15—N17	177.3 (3)
N9—C4—C5—N7	0.2 (3)	N19—C14—C15—N17	−1.2 (4)
N3—C4—C5—C6	0.5 (5)	N13—C14—C15—C16	0.2 (5)
N9—C4—C5—C6	−179.5 (3)	N19—C14—C15—C16	−178.3 (3)
C2—N1—C6—O6	−179.9 (3)	C12—N11—C16—O16	−177.3 (3)
C2—N1—C6—C5	−0.1 (4)	C12—N11—C16—C15	1.5 (4)
C4—C5—C6—O6	179.8 (3)	N17—C15—C16—O16	1.7 (6)
N7—C5—C6—O6	0.2 (6)	C14—C15—C16—O16	178.1 (3)
C4—C5—C6—N1	0.1 (4)	N17—C15—C16—N11	−176.9 (3)
N7—C5—C6—N1	−179.5 (3)	C14—C15—C16—N11	−0.5 (4)
C4—C5—N7—C8	−0.3 (4)	C14—C15—N17—C18	0.0 (4)
C6—C5—N7—C8	179.3 (3)	C16—C15—N17—C18	176.7 (3)
C5—N7—C8—N9	0.4 (4)	C15—N17—C18—N19	1.2 (4)
N7—C8—N9—C4	−0.3 (4)	N13—C14—N19—C18	−176.8 (3)
N7—C8—N9—C1'	−178.9 (3)	C15—C14—N19—C18	1.8 (3)
N3—C4—N9—C8	−179.9 (3)	N13—C14—N19—C11'	−7.1 (5)
C5—C4—N9—C8	0.0 (3)	C15—C14—N19—C11'	171.5 (3)
N3—C4—N9—C1'	−1.3 (5)	N17—C18—N19—C14	−2.0 (4)
C5—C4—N9—C1'	178.7 (3)	N17—C18—N19—C11'	−171.3 (3)
C8—N9—C1'—O1	38.3 (5)	C14—N19—C11'—O11	−178.9 (3)
C4—N9—C1'—O1	−140.0 (3)	C18—N19—C11'—O11	−11.6 (4)
C8—N9—C1'—C2'	−79.4 (4)	C14—N19—C11'—C12'	61.3 (4)
C4—N9—C1'—C2'	102.3 (4)	C18—N19—C11'—C12'	−131.4 (3)
O1—C1'—C2'—O2	92.1 (3)	O11—C11'—C12'—O12	114.1 (3)
N9—C1'—C2'—O2	−149.7 (3)	N19—C11'—C12'—O12	−125.7 (3)
O1—C1'—C2'—C3'	−15.9 (4)	O11—C11'—C12'—C13'	0.8 (3)
N9—C1'—C2'—C3'	102.2 (3)	N19—C11'—C12'—C13'	121.0 (3)
O2—C2'—C3'—O3	29.8 (4)	N19—C11'—O11—C14'	−104.6 (3)
C1'—C2'—C3'—O3	143.9 (3)	C12'—C11'—O11—C14'	17.9 (4)
O2—C2'—C3'—C4'	−88.5 (3)	C13'—C12'—O12—C130	10.4 (4)
C1'—C2'—C3'—C4'	25.6 (4)	C11'—C12'—O12—C130	−101.5 (4)
N9—C1'—O1—C4'	−122.1 (3)	C130—O13—C13'—C14'	138.7 (4)
C2'—C1'—O1—C4'	−1.1 (4)	C130—O13—C13'—C12'	26.6 (5)
C1'—C2'—O2—C30	−146.2 (3)	O12—C12'—C13'—O13	−22.4 (4)
C3'—C2'—O2—C30	−35.3 (4)	C11'—C12'—C13'—O13	96.8 (3)
C4'—C3'—O3—C30	97.3 (4)	O12—C12'—C13'—C14'	−137.2 (3)
C2'—C3'—O3—C30	−13.9 (4)	C11'—C12'—C13'—C14'	−18.0 (4)
C1'—O1—C4'—C5'	144.7 (3)	C11'—O11—C14'—C13'	−29.4 (4)
C1'—O1—C4'—C3'	17.8 (4)	C11'—O11—C14'—C15'	92.1 (4)
O3—C3'—C4'—O1	−139.0 (3)	O13—C13'—C14'—O11	−81.7 (4)
C2'—C3'—C4'—O1	−26.4 (4)	C12'—C13'—C14'—O11	28.8 (4)
O3—C3'—C4'—C5'	99.4 (4)	O13—C13'—C14'—C15'	160.1 (3)
C2'—C3'—C4'—C5'	−147.9 (3)	C12'—C13'—C14'—C15'	−89.3 (4)
O1—C4'—C5'—O51	−69.8 (4)	O11—C14'—C15'—O151	168.8 (4)
C3'—C4'—C5'—O51	50.2 (5)	C13'—C14'—C15'—O151	−75.3 (4)
N3—C2—N21—C22	−179.0 (3)	N13—C12—N121—C122	175.0 (4)
N1—C2—N21—C22	0.9 (5)	N11—C12—N121—C122	−4.9 (5)
C2—N21—C22—O22	3.1 (7)	C12—N121—C122—O122	0.1 (7)
C2—N21—C22—C23	−176.7 (4)	C12—N121—C122—C123	−178.5 (4)
C2'—O2—C30—O3	28.0 (4)	C13'—O13—C130—O12	−21.0 (5)
C2'—O2—C30—C31	−88.6 (4)	C13'—O13—C130—C131	98.9 (5)
C2'—O2—C30—C32	145.8 (4)	C13'—O13—C130—C132	−137.3 (4)
C3'—O3—C30—O2	−7.7 (5)	C12'—O12—C130—O13	5.8 (5)
C3'—O3—C30—C31	110.0 (4)	C12'—O12—C130—C131	−116.9 (5)
C3'—O3—C30—C32	−123.8 (4)	C12'—O12—C130—C132	120.4 (4)
C4'—C5'—O51—C52	−170.8 (4)	C14'—C15'—O151—C152	−105.0 (5)
C5'—O51—C52—O52	0.0 (9)	C15'—O151—C152—O152	2.8 (9)
C5'—O51—C52—C53	−179.7 (5)	C15'—O151—C152—C153	−174.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O22	0.77 (6)	2.00 (6)	2.649 (4)	142 (5)
N11—H11···O122	0.89 (5)	2.01 (5)	2.690 (5)	133 (4)
N21—H21···O1Wⁱ	0.89 (4)	1.88 (4)	2.757 (4)	168 (4)
N121—H121···O2Wⁱⁱ	0.95 (5)	1.98 (5)	2.915 (5)	169 (4)
O2W—H2WA···N17	0.91	2.00	2.885 (4)	162
O1W—H1WA···N7	0.87	1.91	2.775 (4)	173
O2W—H2WB···O1Wⁱⁱⁱ	0.87	2.15	3.011 (5)	170

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) x−1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₅O₇·H₂O
M_r	425.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	6.595 (1), 9.688 (1), 16.301 (1)
α, β, γ (°)	72.72 (1), 89.68 (1), 83.82 (1)
V (Å³)	988.34 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.50 × 0.23 × 0.16

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6620, 5699, 4093
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.711

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.148, 1.03
No. of reflections	5699
No. of parameters	557
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.24

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), SET4 in CAD-4 EXPRESS, HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006), SHELXL97.