Crystal structure and sequential dehydration transitions of disodium guanosine 5′-monophos­phate tetra­hydrate

Disodium guanosine 5′-monophosphate was reported previously to crystallize as both the tetra­hydrate and the hepta­hydrate. We herein report a determination of the mol­ecular and crystal structures of the title tetrahydrated salt, 2Na⁺·C₁₀H₁₂N₅O₈P²⁻·4H₂O. It was found that the structure differs markedly from that of the hepta­hydrate, but greatly resembles that of disodium de­oxy­guanosine 5′-monophosphate tetra­hydrate. The C2′—O2′H moiety of ribose is surrounded by hydro­philic moieties and is disordered over two sites. The sugar puckering mode is O4′-endo-C1′-exo at both sites and the conformation around the C4′—C5′ bond is gauche–trans. Powder X-ray diffraction and thermal analyses revealed that the temperature-controlled transition from the tetra­hydrate to the anhydride proceeded through three inter­mediate phases between 40 and 60 °C at 0% relative humidity. Large induction periods were observed.

Computing details

Data collection: CrystalClear (Rigaku, 2006); cell refinement: CrystalClear (Rigaku, 2006); data reduction: CrystalClear (Rigaku, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(I)

Crystal data

2Na^+·C10H12N5O8P^2^−·4H2O	F(000) = 496
Mr = 479.26	Dx = 1.709 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.7107 Å
a = 5.5965 (8) Å	Cell parameters from 527 reflections
b = 10.7222 (17) Å	θ = 10–15°
c = 15.710 (3) Å	µ = 0.27 mm^−1
β = 98.796 (9)°	T = 299 K
V = 931.6 (3) Å^3	Plate, colourless
Z = 2	0.50 × 0.40 × 0.05 mm

Data collection

Rigaku MERCURY CCD diffractometer	4037 independent reflections
Radiation source: Rotating Anode	3700 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 7.31 pixels mm^-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −6→7
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	k = −13→13
Tmin = 0.877, Tmax = 0.987	l = −20→20
7321 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0357P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.002
4037 reflections	Δρmax = 0.24 e Å^−3
276 parameters	Δρmin = −0.25 e Å^−3
3 restraints	Absolute structure: Flack x determined using 1155 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.2134 (4)	0.4626 (3)	0.70364 (15)	0.0252 (5)
H1	0.1476	0.4858	0.7471	0.030*
C2	0.1221 (5)	0.5116 (3)	0.62554 (17)	0.0245 (6)
N2	−0.0628 (5)	0.5917 (3)	0.62266 (18)	0.0393 (7)
H1N2	−0.1241	0.6252	0.5745	0.047*
H2N2	−0.1202	0.6095	0.6689	0.047*
N3	0.2070 (4)	0.4858 (3)	0.55320 (14)	0.0260 (5)
C4	0.3956 (5)	0.4055 (3)	0.56689 (18)	0.0241 (6)
C5	0.4960 (5)	0.3489 (3)	0.64213 (18)	0.0251 (6)
C6	0.4027 (5)	0.3787 (3)	0.71924 (19)	0.0233 (6)
O6	0.4716 (4)	0.3394 (2)	0.79324 (13)	0.0303 (5)
N7	0.6873 (5)	0.2725 (3)	0.62867 (16)	0.0300 (6)
C8	0.6990 (6)	0.2842 (3)	0.54635 (19)	0.0302 (7)
H8	0.8125	0.2432	0.5190	0.036*
N9	0.5259 (5)	0.3634 (3)	0.50459 (16)	0.0265 (6)
C1'	0.5013 (5)	0.4065 (3)	0.41620 (18)	0.0248 (6)
H1'	0.3912	0.4781	0.4077	0.030*
C2'A	0.736 (3)	0.4368 (13)	0.3841 (7)	0.0329 (13)	0.5
H2'A	0.8464	0.3669	0.4005	0.039*	0.5
O2'A	0.8593 (9)	0.5458 (6)	0.4132 (3)	0.0329 (13)	0.5
C2'B	0.730 (3)	0.4544 (13)	0.3878 (8)	0.0326 (13)	0.5
H2'B	0.8706	0.4046	0.4128	0.039*	0.5
O2'B	0.7594 (10)	0.5837 (5)	0.4143 (3)	0.0326 (13)	0.5
C3'	0.6691 (5)	0.4331 (3)	0.28750 (18)	0.0248 (6)
H3'	0.7992	0.3941	0.2617	0.030*
O3'	0.6091 (4)	0.5495 (2)	0.24854 (13)	0.0359 (6)
H3'O	0.7494	0.5846	0.2450	0.050*
C4'	0.4446 (5)	0.3486 (3)	0.27548 (17)	0.0221 (6)
H4'	0.3029	0.3966	0.2495	0.026*
O4'	0.4121 (4)	0.3079 (2)	0.36071 (13)	0.0353 (6)
C5'	0.4738 (5)	0.2375 (3)	0.22129 (19)	0.0267 (6)
H5''	0.4921	0.2645	0.1637	0.032*
H5'	0.6194	0.1929	0.2454	0.032*
O5'	0.2696 (4)	0.1549 (2)	0.21646 (12)	0.0290 (5)
P1	0.10363 (13)	0.1293	0.12416 (4)	0.01985 (16)
O1	0.2605 (4)	0.0701 (2)	0.06450 (13)	0.0293 (5)
O2	−0.0855 (4)	0.0416 (2)	0.14771 (13)	0.0311 (5)
O3	0.0022 (4)	0.2532 (2)	0.08967 (14)	0.0328 (5)
Na1	0.3453 (2)	0.65391 (14)	0.14192 (8)	0.0340 (3)
Na2	0.5886 (2)	0.93330 (13)	0.07010 (8)	0.0288 (3)
O1W	0.0250 (4)	0.6577 (2)	0.23455 (14)	0.0402 (6)
H11W	−0.0067	0.7332	0.1987	0.050*
H12W	0.1127	0.6865	0.2796	0.050*
O2W	−0.0011 (4)	0.7968 (2)	0.08815 (14)	0.0359 (5)
H21W	−0.0169	0.7782	0.0342	0.050*
H22W	0.0358	0.8822	0.0997	0.050*
O3W	0.1588 (5)	0.4883 (2)	0.06080 (15)	0.0444 (6)
H31W	0.0037	0.5195	0.0335	0.050*
H32W	0.1181	0.4045	0.0856	0.050*
O4W	0.4574 (4)	0.7386 (2)	0.00945 (14)	0.0322 (5)
H41W	0.3271	0.7317	−0.0231	0.050*
H42W	0.5636	0.6841	−0.0150	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0292 (13)	0.0287 (14)	0.0184 (11)	0.0071 (11)	0.0063 (10)	−0.0011 (10)
C2	0.0276 (16)	0.0258 (16)	0.0200 (14)	0.0006 (13)	0.0035 (12)	−0.0011 (12)
N2	0.0413 (16)	0.0494 (19)	0.0275 (14)	0.0234 (14)	0.0064 (12)	0.0053 (13)
N3	0.0270 (13)	0.0317 (14)	0.0191 (12)	0.0058 (11)	0.0036 (10)	0.0002 (11)
C4	0.0275 (15)	0.0245 (16)	0.0201 (14)	−0.0012 (12)	0.0030 (12)	−0.0023 (12)
C5	0.0303 (16)	0.0265 (16)	0.0186 (14)	0.0024 (13)	0.0039 (11)	−0.0004 (12)
C6	0.0267 (15)	0.0231 (15)	0.0206 (14)	−0.0003 (12)	0.0051 (11)	0.0016 (12)
O6	0.0410 (12)	0.0322 (13)	0.0174 (10)	0.0111 (10)	0.0034 (9)	0.0043 (9)
N7	0.0351 (14)	0.0318 (15)	0.0243 (13)	0.0112 (12)	0.0087 (11)	0.0024 (11)
C8	0.0334 (17)	0.0335 (18)	0.0254 (15)	0.0077 (14)	0.0101 (13)	0.0008 (13)
N9	0.0321 (14)	0.0312 (15)	0.0174 (11)	0.0065 (12)	0.0073 (10)	−0.0005 (11)
C1'	0.0305 (16)	0.0262 (17)	0.0173 (14)	−0.0001 (13)	0.0029 (11)	−0.0021 (11)
C2'A	0.030 (2)	0.039 (3)	0.026 (2)	−0.014 (2)	−0.0073 (16)	0.0067 (19)
O2'A	0.030 (2)	0.039 (3)	0.026 (2)	−0.014 (2)	−0.0073 (16)	0.0067 (19)
C2'B	0.039 (2)	0.032 (3)	0.024 (2)	−0.008 (2)	−0.0040 (18)	−0.0028 (18)
O2'B	0.039 (2)	0.032 (3)	0.024 (2)	−0.008 (2)	−0.0040 (18)	−0.0028 (18)
C3'	0.0268 (15)	0.0264 (16)	0.0220 (14)	−0.0026 (13)	0.0062 (11)	0.0005 (13)
O3'	0.0392 (13)	0.0342 (13)	0.0305 (12)	−0.0134 (11)	−0.0067 (10)	0.0132 (10)
C4'	0.0240 (15)	0.0243 (15)	0.0187 (13)	−0.0039 (12)	0.0058 (11)	0.0012 (11)
O4'	0.0484 (14)	0.0422 (14)	0.0176 (10)	−0.0241 (11)	0.0125 (9)	−0.0071 (10)
C5'	0.0261 (15)	0.0298 (17)	0.0236 (15)	−0.0072 (14)	0.0022 (11)	−0.0073 (13)
O5'	0.0332 (11)	0.0335 (12)	0.0193 (9)	−0.0125 (10)	0.0012 (8)	−0.0029 (9)
P1	0.0236 (4)	0.0199 (4)	0.0159 (3)	−0.0029 (3)	0.0026 (3)	−0.0006 (3)
O1	0.0294 (11)	0.0335 (12)	0.0255 (10)	0.0016 (9)	0.0058 (8)	−0.0072 (9)
O2	0.0345 (12)	0.0365 (13)	0.0220 (10)	−0.0164 (10)	0.0039 (9)	0.0037 (9)
O3	0.0383 (12)	0.0245 (13)	0.0341 (12)	0.0031 (10)	0.0004 (10)	0.0048 (10)
Na1	0.0426 (7)	0.0315 (7)	0.0258 (6)	−0.0041 (6)	−0.0014 (5)	0.0007 (6)
Na2	0.0285 (6)	0.0290 (7)	0.0282 (6)	−0.0017 (5)	0.0025 (5)	−0.0045 (5)
O1W	0.0395 (12)	0.0466 (15)	0.0328 (12)	−0.0157 (11)	0.0006 (10)	0.0029 (11)
O2W	0.0466 (13)	0.0330 (13)	0.0287 (12)	−0.0020 (11)	0.0077 (10)	−0.0030 (10)
O3W	0.0587 (16)	0.0314 (13)	0.0375 (13)	−0.0056 (12)	−0.0105 (11)	0.0020 (11)
O4W	0.0281 (11)	0.0394 (13)	0.0300 (12)	−0.0030 (10)	0.0069 (9)	−0.0099 (10)

Geometric parameters (Å, º)

N1—C2	1.360 (4)	C4'—H4'	0.9800
N1—C6	1.383 (4)	C5'—O5'	1.438 (3)
N1—H1	0.8600	C5'—H5''	0.9700
C2—N3	1.326 (3)	C5'—H5'	0.9700
C2—N2	1.340 (4)	O5'—P1	1.621 (2)
N2—H1N2	0.8600	P1—O2	1.503 (2)
N2—H2N2	0.8600	P1—O3	1.512 (2)
N3—C4	1.354 (4)	P1—O1	1.517 (2)
C4—C5	1.370 (4)	O1—Na2^ii	2.342 (2)
C4—N9	1.382 (4)	O2—Na2^iii	2.341 (2)
C5—N7	1.390 (4)	Na1—O3W	2.337 (3)
C5—C6	1.426 (4)	Na1—O6^iv	2.392 (2)
C6—O6	1.241 (4)	Na1—O4W	2.439 (2)
O6—Na1^i	2.392 (2)	Na1—O1W	2.476 (3)
O6—Na2^i	2.441 (2)	Na1—O2W	2.514 (3)
N7—C8	1.311 (4)	Na1—Na2	3.5456 (18)
C8—N9	1.377 (4)	Na1—Na2^v	4.1476 (18)
C8—H8	0.9300	Na1—H3'O	2.6776
N9—C1'	1.450 (4)	Na1—H11W	2.4368
C1'—O4'	1.412 (3)	Na2—O2^vi	2.341 (2)
C1'—C2'B	1.511 (13)	Na2—O1^vii	2.342 (2)
C1'—C2'A	1.512 (12)	Na2—O4W	2.365 (3)
C1'—H1'	0.9800	Na2—O6^iv	2.441 (2)
C2'A—O2'A	1.399 (10)	Na2—O2W^viii	2.701 (3)
C2'A—C3'	1.507 (12)	Na2—O3W^ix	2.732 (3)
C2'A—H2'A	0.9800	Na2—Na1^ix	4.1476 (18)
C2'B—O2'B	1.448 (11)	O1W—H11W	0.9860
C2'B—C3'	1.578 (12)	O1W—H12W	0.8548
C2'B—H2'B	0.9800	O2W—Na2^x	2.701 (3)
C3'—O3'	1.407 (4)	O2W—H21W	0.8619
C3'—C4'	1.538 (4)	O2W—H22W	0.9498
C3'—H3'	0.9800	O3W—Na2^v	2.732 (3)
O3'—Na1	2.342 (2)	O3W—H31W	0.9670
O3'—H3'O	0.8801	O3W—H32W	1.0184
C4'—O4'	1.446 (3)	O4W—H41W	0.8274
C4'—C5'	1.488 (4)	O4W—H42W	0.9548
C2—N1—C6	125.7 (2)	O3W—Na1—O1W	91.72 (9)
C2—N1—H1	117.2	O3'—Na1—O1W	91.23 (9)
C6—N1—H1	117.2	O6^iv—Na1—O1W	92.15 (9)
N3—C2—N2	118.7 (3)	O4W—Na1—O1W	143.06 (9)
N3—C2—N1	123.9 (3)	O3W—Na1—O2W	91.30 (9)
N2—C2—N1	117.4 (2)	O3'—Na1—O2W	154.34 (10)
C2—N2—H1N2	120.0	O6^iv—Na1—O2W	83.95 (9)
C2—N2—H2N2	120.0	O4W—Na1—O2W	76.83 (8)
H1N2—N2—H2N2	120.0	O1W—Na1—O2W	66.23 (8)
C2—N3—C4	111.7 (2)	O3W—Na1—Na2	129.04 (8)
N3—C4—C5	128.7 (3)	O3'—Na1—Na2	113.63 (7)
N3—C4—N9	125.3 (3)	O6^iv—Na1—Na2	43.35 (6)
C5—C4—N9	106.0 (3)	O4W—Na1—Na2	41.63 (6)
C4—C5—N7	110.7 (3)	O1W—Na1—Na2	121.39 (8)
C4—C5—C6	118.6 (3)	O2W—Na1—Na2	72.06 (6)
N7—C5—C6	130.7 (3)	O3W—Na1—Na2^v	38.36 (7)
O6—C6—N1	120.4 (3)	O3'—Na1—Na2^v	100.24 (7)
O6—C6—C5	128.1 (3)	O6^iv—Na1—Na2^v	136.97 (7)
N1—C6—C5	111.4 (2)	O4W—Na1—Na2^v	57.37 (6)
C6—O6—Na1^i	137.11 (19)	O1W—Na1—Na2^v	130.01 (7)
C6—O6—Na2^i	128.22 (19)	O2W—Na1—Na2^v	103.69 (7)
Na1^i—O6—Na2^i	94.37 (8)	Na2—Na1—Na2^v	98.08 (3)
C8—N7—C5	104.5 (3)	O3W—Na1—H3'O	112.6
N7—C8—N9	113.0 (3)	O3'—Na1—H3'O	18.7
N7—C8—H8	123.5	O6^iv—Na1—H3'O	72.9
N9—C8—H8	123.5	O4W—Na1—H3'O	108.4
C8—N9—C4	105.8 (2)	O1W—Na1—H3'O	105.6
C8—N9—C1'	127.6 (2)	O2W—Na1—H3'O	155.4
C4—N9—C1'	126.2 (2)	Na2—Na1—H3'O	95.6
O4'—C1'—N9	109.0 (2)	Na2^v—Na1—H3'O	99.0
O4'—C1'—C2'B	108.0 (4)	O3W—Na1—H11W	98.4
N9—C1'—C2'B	115.5 (6)	O3'—Na1—H11W	111.2
O4'—C1'—C2'A	101.4 (5)	O6^iv—Na1—H11W	82.6
N9—C1'—C2'A	115.3 (6)	O4W—Na1—H11W	120.7
O4'—C1'—H1'	110.3	O1W—Na1—H11W	23.1
N9—C1'—H1'	110.3	O2W—Na1—H11W	44.4
C2'A—C1'—H1'	110.3	Na2—Na1—H11W	101.1
O2'A—C2'A—C3'	112.6 (8)	Na2^v—Na1—H11W	132.0
O2'A—C2'A—C1'	118.7 (9)	H3'O—Na1—H11W	122.1
C3'—C2'A—C1'	103.6 (8)	O2^vi—Na2—O1^vii	104.64 (9)
O2'A—C2'A—H2'A	107.1	O2^vi—Na2—O4W	144.77 (9)
C3'—C2'A—H2'A	107.1	O1^vii—Na2—O4W	110.16 (9)
C1'—C2'A—H2'A	107.1	O2^vi—Na2—O6^iv	87.01 (8)
O2'B—C2'B—C1'	107.7 (9)	O1^vii—Na2—O6^iv	94.51 (8)
O2'B—C2'B—C3'	115.0 (9)	O4W—Na2—O6^iv	85.06 (8)
C1'—C2'B—C3'	100.4 (7)	O2^vi—Na2—O2W^viii	68.41 (8)
O2'B—C2'B—H2'B	111.1	O1^vii—Na2—O2W^viii	173.05 (9)
C1'—C2'B—H2'B	111.1	O4W—Na2—O2W^viii	76.73 (8)
C3'—C2'B—H2'B	111.1	O6^iv—Na2—O2W^viii	85.04 (8)
O3'—C3'—C2'A	114.9 (6)	O2^vi—Na2—O3W^ix	80.41 (8)
O3'—C3'—C4'	109.5 (2)	O1^vii—Na2—O3W^ix	109.25 (8)
C2'A—C3'—C4'	102.2 (4)	O4W—Na2—O3W^ix	92.97 (8)
O3'—C3'—C2'B	107.9 (6)	O6^iv—Na2—O3W^ix	155.23 (9)
C4'—C3'—C2'B	104.9 (5)	O2W^viii—Na2—O3W^ix	70.52 (8)
O3'—C3'—H3'	110.0	O2^vi—Na2—Na1	124.05 (7)
C2'A—C3'—H3'	110.0	O1^vii—Na2—Na1	101.78 (7)
C4'—C3'—H3'	110.0	O4W—Na2—Na1	43.24 (6)
C3'—O3'—Na1	144.81 (18)	O6^iv—Na2—Na1	42.28 (5)
C3'—O3'—H3'O	104.5	O2W^viii—Na2—Na1	82.56 (6)
Na1—O3'—H3'O	102.8	O3W^ix—Na2—Na1	133.63 (7)
O4'—C4'—C5'	109.2 (2)	O2^vi—Na2—Na1^ix	88.70 (6)
O4'—C4'—C3'	106.3 (2)	O1^vii—Na2—Na1^ix	77.19 (6)
C5'—C4'—C3'	112.5 (2)	O4W—Na2—Na1^ix	103.91 (7)
O4'—C4'—H4'	109.6	O6^iv—Na2—Na1^ix	169.38 (7)
C5'—C4'—H4'	109.6	O2W^viii—Na2—Na1^ix	102.39 (6)
C3'—C4'—H4'	109.6	O3W^ix—Na2—Na1^ix	32.06 (5)
C1'—O4'—C4'	105.3 (2)	Na1—Na2—Na1^ix	145.40 (4)
O5'—C5'—C4'	111.5 (2)	Na1—O1W—H11W	76.2
O5'—C5'—H5''	109.3	Na1—O1W—H12W	96.7
C4'—C5'—H5''	109.3	H11W—O1W—H12W	102.0
O5'—C5'—H5'	109.3	Na1—O2W—Na2^x	164.82 (10)
C4'—C5'—H5'	109.3	Na1—O2W—H21W	98.4
H5''—C5'—H5'	108.0	Na2^x—O2W—H21W	93.7
C5'—O5'—P1	119.58 (18)	Na1—O2W—H22W	112.9
O2—P1—O3	113.42 (13)	Na2^x—O2W—H22W	69.8
O2—P1—O1	112.73 (12)	H21W—O2W—H22W	113.4
O3—P1—O1	111.51 (13)	Na1—O3W—Na2^v	109.58 (10)
O2—P1—O5'	102.40 (11)	Na1—O3W—H31W	105.9
O3—P1—O5'	107.68 (12)	Na2^v—O3W—H31W	105.9
O1—P1—O5'	108.47 (12)	Na1—O3W—H32W	124.6
P1—O1—Na2^ii	139.73 (13)	Na2^v—O3W—H32W	105.6
P1—O2—Na2^iii	134.72 (12)	H31W—O3W—H32W	103.7
O3W—Na1—O3'	101.94 (10)	Na2—O4W—Na1	95.13 (8)
O3W—Na1—O6^iv	172.09 (10)	Na2—O4W—H41W	121.2
O3'—Na1—O6^iv	84.88 (8)	Na1—O4W—H41W	100.2
O3W—Na1—O4W	88.24 (9)	Na2—O4W—H42W	121.9
O3'—Na1—O4W	124.89 (9)	Na1—O4W—H42W	111.9
O6^iv—Na1—O4W	84.53 (8)	H41W—O4W—H42W	103.9
C6—N1—C2—N3	−0.9 (5)	O4'—C1'—C2'B—O2'B	153.8 (7)
C6—N1—C2—N2	179.9 (3)	N9—C1'—C2'B—O2'B	−84.0 (10)
N2—C2—N3—C4	178.9 (3)	O4'—C1'—C2'B—C3'	33.2 (9)
N1—C2—N3—C4	−0.3 (4)	N9—C1'—C2'B—C3'	155.4 (5)
C2—N3—C4—C5	2.2 (4)	O2'A—C2'A—C3'—O3'	−34.7 (12)
C2—N3—C4—N9	−178.3 (3)	C1'—C2'A—C3'—O3'	94.8 (7)
N3—C4—C5—N7	179.8 (3)	O2'A—C2'A—C3'—C4'	−153.2 (9)
N9—C4—C5—N7	0.3 (3)	C1'—C2'A—C3'—C4'	−23.6 (9)
N3—C4—C5—C6	−2.7 (5)	O2'B—C2'B—C3'—O3'	−11.8 (11)
N9—C4—C5—C6	177.7 (3)	C1'—C2'B—C3'—O3'	103.4 (7)
C2—N1—C6—O6	−179.8 (3)	O2'B—C2'B—C3'—C4'	−128.4 (9)
C2—N1—C6—C5	0.4 (4)	C1'—C2'B—C3'—C4'	−13.2 (9)
C4—C5—C6—O6	−178.6 (3)	C2'A—C3'—O3'—Na1	−139.3 (6)
N7—C5—C6—O6	−1.7 (6)	C4'—C3'—O3'—Na1	−25.0 (4)
C4—C5—C6—N1	1.2 (4)	C2'B—C3'—O3'—Na1	−138.6 (6)
N7—C5—C6—N1	178.1 (3)	O3'—C3'—C4'—O4'	−125.2 (2)
N1—C6—O6—Na1^i	150.7 (2)	C2'A—C3'—C4'—O4'	−2.9 (7)
C5—C6—O6—Na1^i	−29.6 (5)	C2'B—C3'—C4'—O4'	−9.6 (7)
N1—C6—O6—Na2^i	−21.3 (4)	O3'—C3'—C4'—C5'	115.4 (3)
C5—C6—O6—Na2^i	158.5 (2)	C2'A—C3'—C4'—C5'	−122.4 (7)
C4—C5—N7—C8	0.0 (4)	C2'B—C3'—C4'—C5'	−129.1 (7)
C6—C5—N7—C8	−177.1 (3)	N9—C1'—O4'—C4'	−167.4 (2)
C5—N7—C8—N9	−0.3 (4)	C2'B—C1'—O4'—C4'	−41.3 (7)
N7—C8—N9—C4	0.4 (4)	C2'A—C1'—O4'—C4'	−45.4 (7)
N7—C8—N9—C1'	173.6 (3)	C5'—C4'—O4'—C1'	152.3 (2)
N3—C4—N9—C8	−180.0 (3)	C3'—C4'—O4'—C1'	30.7 (3)
C5—C4—N9—C8	−0.4 (3)	O4'—C4'—C5'—O5'	57.8 (3)
N3—C4—N9—C1'	6.7 (5)	C3'—C4'—C5'—O5'	175.5 (2)
C5—C4—N9—C1'	−173.7 (3)	C4'—C5'—O5'—P1	117.1 (2)
C8—N9—C1'—O4'	73.8 (4)	C5'—O5'—P1—O2	−179.4 (2)
C4—N9—C1'—O4'	−114.4 (3)	C5'—O5'—P1—O3	−59.6 (2)
C8—N9—C1'—C2'B	−47.9 (7)	C5'—O5'—P1—O1	61.2 (2)
C4—N9—C1'—C2'B	124.0 (6)	O2—P1—O1—Na2^ii	−78.6 (2)
C8—N9—C1'—C2'A	−39.4 (7)	O3—P1—O1—Na2^ii	152.51 (18)
C4—N9—C1'—C2'A	132.4 (6)	O5'—P1—O1—Na2^ii	34.1 (2)
O4'—C1'—C2'A—O2'A	168.7 (9)	O3—P1—O2—Na2^iii	67.4 (2)
N9—C1'—C2'A—O2'A	−73.8 (12)	O1—P1—O2—Na2^iii	−60.5 (2)
O4'—C1'—C2'A—C3'	42.9 (9)	O5'—P1—O2—Na2^iii	−176.86 (17)
N9—C1'—C2'A—C3'	160.5 (6)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^xi	0.86	1.84	2.682 (4)	166
N2—H1N2···O2′B^x	0.86	2.54	3.274 (7)	144
N2—H2N2···O5′^xi	0.86	2.15	3.014 (4)	179
O2′A···N3^viii			2.780 (7)
O2′B···N7^iv			3.207 (6)
O3′—H3′O···O1W^viii	0.880	1.760	2.640 (4)	177.9
O1W—H11···O2W	0.99	1.87	2.726 (4)	143
O1W—H12···N7^iv	0.86	1.92	2.769 (4)	172
O2W—H21···O3^xii	0.86	1.98	2.831 (3)	170
O2W—H22···O1^vii	0.95	2.48	3.322 (3)	147
O2W—H22···O2^vii	0.95	2.03	2.850 (3)	144
O3W—H31···O1^xii	0.97	2.04	2.956 (4)	158
O3W—H32···O3	1.02	1.75	2.730 (3)	159
O4W—H41···O3^xii	0.83	1.99	2.800 (3)	167
O4W—H42···O1^ix	0.96	1.82	2.768 (3)	174

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