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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.
Supporting information
CCDC reference: 1826037
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).
Crystal data top
2Na+·C10H12N5O8P2−·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) Å3 | Plate, colourless |
Z = 2 | 0.50 × 0.40 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.071 | w = 1/[σ2(Fo2) + (0.0357P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—Na2ii | 2.342 (2) |
C4—N9 | 1.382 (4) | O2—Na2iii | 2.341 (2) |
C5—N7 | 1.390 (4) | Na1—O3W | 2.337 (3) |
C5—C6 | 1.426 (4) | Na1—O6iv | 2.392 (2) |
C6—O6 | 1.241 (4) | Na1—O4W | 2.439 (2) |
O6—Na1i | 2.392 (2) | Na1—O1W | 2.476 (3) |
O6—Na2i | 2.441 (2) | Na1—O2W | 2.514 (3) |
N7—C8 | 1.311 (4) | Na1—Na2 | 3.5456 (18) |
C8—N9 | 1.377 (4) | Na1—Na2v | 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—O2vi | 2.341 (2) |
C1'—C2'B | 1.511 (13) | Na2—O1vii | 2.342 (2) |
C1'—C2'A | 1.512 (12) | Na2—O4W | 2.365 (3) |
C1'—H1' | 0.9800 | Na2—O6iv | 2.441 (2) |
C2'A—O2'A | 1.399 (10) | Na2—O2Wviii | 2.701 (3) |
C2'A—C3' | 1.507 (12) | Na2—O3Wix | 2.732 (3) |
C2'A—H2'A | 0.9800 | Na2—Na1ix | 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—Na2x | 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—Na2v | 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 | O6iv—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 | O6iv—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) | O6iv—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—Na2v | 38.36 (7) |
O6—C6—N1 | 120.4 (3) | O3'—Na1—Na2v | 100.24 (7) |
O6—C6—C5 | 128.1 (3) | O6iv—Na1—Na2v | 136.97 (7) |
N1—C6—C5 | 111.4 (2) | O4W—Na1—Na2v | 57.37 (6) |
C6—O6—Na1i | 137.11 (19) | O1W—Na1—Na2v | 130.01 (7) |
C6—O6—Na2i | 128.22 (19) | O2W—Na1—Na2v | 103.69 (7) |
Na1i—O6—Na2i | 94.37 (8) | Na2—Na1—Na2v | 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 | O6iv—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) | Na2v—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) | O6iv—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) | Na2v—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) | O2vi—Na2—O1vii | 104.64 (9) |
O2'A—C2'A—H2'A | 107.1 | O2vi—Na2—O4W | 144.77 (9) |
C3'—C2'A—H2'A | 107.1 | O1vii—Na2—O4W | 110.16 (9) |
C1'—C2'A—H2'A | 107.1 | O2vi—Na2—O6iv | 87.01 (8) |
O2'B—C2'B—C1' | 107.7 (9) | O1vii—Na2—O6iv | 94.51 (8) |
O2'B—C2'B—C3' | 115.0 (9) | O4W—Na2—O6iv | 85.06 (8) |
C1'—C2'B—C3' | 100.4 (7) | O2vi—Na2—O2Wviii | 68.41 (8) |
O2'B—C2'B—H2'B | 111.1 | O1vii—Na2—O2Wviii | 173.05 (9) |
C1'—C2'B—H2'B | 111.1 | O4W—Na2—O2Wviii | 76.73 (8) |
C3'—C2'B—H2'B | 111.1 | O6iv—Na2—O2Wviii | 85.04 (8) |
O3'—C3'—C2'A | 114.9 (6) | O2vi—Na2—O3Wix | 80.41 (8) |
O3'—C3'—C4' | 109.5 (2) | O1vii—Na2—O3Wix | 109.25 (8) |
C2'A—C3'—C4' | 102.2 (4) | O4W—Na2—O3Wix | 92.97 (8) |
O3'—C3'—C2'B | 107.9 (6) | O6iv—Na2—O3Wix | 155.23 (9) |
C4'—C3'—C2'B | 104.9 (5) | O2Wviii—Na2—O3Wix | 70.52 (8) |
O3'—C3'—H3' | 110.0 | O2vi—Na2—Na1 | 124.05 (7) |
C2'A—C3'—H3' | 110.0 | O1vii—Na2—Na1 | 101.78 (7) |
C4'—C3'—H3' | 110.0 | O4W—Na2—Na1 | 43.24 (6) |
C3'—O3'—Na1 | 144.81 (18) | O6iv—Na2—Na1 | 42.28 (5) |
C3'—O3'—H3'O | 104.5 | O2Wviii—Na2—Na1 | 82.56 (6) |
Na1—O3'—H3'O | 102.8 | O3Wix—Na2—Na1 | 133.63 (7) |
O4'—C4'—C5' | 109.2 (2) | O2vi—Na2—Na1ix | 88.70 (6) |
O4'—C4'—C3' | 106.3 (2) | O1vii—Na2—Na1ix | 77.19 (6) |
C5'—C4'—C3' | 112.5 (2) | O4W—Na2—Na1ix | 103.91 (7) |
O4'—C4'—H4' | 109.6 | O6iv—Na2—Na1ix | 169.38 (7) |
C5'—C4'—H4' | 109.6 | O2Wviii—Na2—Na1ix | 102.39 (6) |
C3'—C4'—H4' | 109.6 | O3Wix—Na2—Na1ix | 32.06 (5) |
C1'—O4'—C4' | 105.3 (2) | Na1—Na2—Na1ix | 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—Na2x | 164.82 (10) |
C4'—C5'—H5' | 109.3 | Na1—O2W—H21W | 98.4 |
H5''—C5'—H5' | 108.0 | Na2x—O2W—H21W | 93.7 |
C5'—O5'—P1 | 119.58 (18) | Na1—O2W—H22W | 112.9 |
O2—P1—O3 | 113.42 (13) | Na2x—O2W—H22W | 69.8 |
O2—P1—O1 | 112.73 (12) | H21W—O2W—H22W | 113.4 |
O3—P1—O1 | 111.51 (13) | Na1—O3W—Na2v | 109.58 (10) |
O2—P1—O5' | 102.40 (11) | Na1—O3W—H31W | 105.9 |
O3—P1—O5' | 107.68 (12) | Na2v—O3W—H31W | 105.9 |
O1—P1—O5' | 108.47 (12) | Na1—O3W—H32W | 124.6 |
P1—O1—Na2ii | 139.73 (13) | Na2v—O3W—H32W | 105.6 |
P1—O2—Na2iii | 134.72 (12) | H31W—O3W—H32W | 103.7 |
O3W—Na1—O3' | 101.94 (10) | Na2—O4W—Na1 | 95.13 (8) |
O3W—Na1—O6iv | 172.09 (10) | Na2—O4W—H41W | 121.2 |
O3'—Na1—O6iv | 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 |
O6iv—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—Na1i | 150.7 (2) | C2'A—C3'—C4'—O4' | −2.9 (7) |
C5—C6—O6—Na1i | −29.6 (5) | C2'B—C3'—C4'—O4' | −9.6 (7) |
N1—C6—O6—Na2i | −21.3 (4) | O3'—C3'—C4'—C5' | 115.4 (3) |
C5—C6—O6—Na2i | 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—Na2ii | −78.6 (2) |
C8—N9—C1'—C2'A | −39.4 (7) | O3—P1—O1—Na2ii | 152.51 (18) |
C4—N9—C1'—C2'A | 132.4 (6) | O5'—P1—O1—Na2ii | 34.1 (2) |
O4'—C1'—C2'A—O2'A | 168.7 (9) | O3—P1—O2—Na2iii | 67.4 (2) |
N9—C1'—C2'A—O2'A | −73.8 (12) | O1—P1—O2—Na2iii | −60.5 (2) |
O4'—C1'—C2'A—C3' | 42.9 (9) | O5'—P1—O2—Na2iii | −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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2xi | 0.86 | 1.84 | 2.682 (4) | 166 |
N2—H1N2···O2′Bx | 0.86 | 2.54 | 3.274 (7) | 144 |
N2—H2N2···O5′xi | 0.86 | 2.15 | 3.014 (4) | 179 |
O2′A···N3viii | | | 2.780 (7) | |
O2′B···N7iv | | | 3.207 (6) | |
O3′—H3′O···O1Wviii | 0.880 | 1.760 | 2.640 (4) | 177.9 |
O1W—H11···O2W | 0.99 | 1.87 | 2.726 (4) | 143 |
O1W—H12···N7iv | 0.86 | 1.92 | 2.769 (4) | 172 |
O2W—H21···O3xii | 0.86 | 1.98 | 2.831 (3) | 170 |
O2W—H22···O1vii | 0.95 | 2.48 | 3.322 (3) | 147 |
O2W—H22···O2vii | 0.95 | 2.03 | 2.850 (3) | 144 |
O3W—H31···O1xii | 0.97 | 2.04 | 2.956 (4) | 158 |
O3W—H32···O3 | 1.02 | 1.75 | 2.730 (3) | 159 |
O4W—H41···O3xii | 0.83 | 1.99 | 2.800 (3) | 167 |
O4W—H42···O1ix | 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. |
Coordination distances (Å) around sodium ions topNa1···O3' | 2.342 (2) | Na1···O3W | 2.337 (3) |
Na1···O1W | 2.476 (3) | Na1···O4W | 2.439 (3) |
Na1···O2W | 2.514 (3) | Na1···O6i | 2.392 (2) |
| | | |
Na2···O1ii | 2.342 (2) | Na2···O4W | 2.365 (3) |
Na2···O2iii | 2.341 (2) | Na2···O6i | 2.441 (2) |
Na2···O2Wiv | 2.701 (3) | Na2···O3Wv' | 2.732 (3) |
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, z;
(v) -x+1, y+1/2, -z. |
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