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Reported here is the crystal structure of a heterocycle that implements a donor–donor–acceptor hydrogen-bonding pattern, as found in the Z component [6-amino-5-nitro­pyridin-2(1H)-one] of an artificially expanded genetic information system (AEGIS). AEGIS is a new form of DNA from synthetic biology that has six replicable nucleotides, rather than the four found in natural DNA. Remarkably, Z crystallizes from water as a 1:1 complex of its neutral and deprotonated forms, and forms a `skinny' pyrimidine–pyrimidine pair in this structure. The pair resembles the known inter­calated cytosine pair. The formation of the same pair in two different salts, namely poly[[aqua­(μ6-2-amino-6-oxo-3-nitro-1,6-di­hydro­pyridin-1-ido)sodium]–6-amino-5-nitro­pyridin-2(1H)-one–water (1/1/1)], denoted Z-Sod, {[Na(C5H4N3O3)(H2O)]·C5H5N3O3·H2O}n, and ammonium 2-amino-6-oxo-3-nitro-1,6-di­hydro­pyridin-1-ide–6-amino-5-nitro­pyridin-2(1H)-one–water (1/1/1), denoted Z-Am, NH4+·C5H4N3O3·C5H5N3O3·H2O, under two different crystallization conditions suggests that the pair is especially stable. Implications of this structure for the use of this heterocycle in artificial DNA are discussed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616017071/ku3185sup1.cif
Contains datablocks Z-Sod, Z-Am

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616017071/ku3185Z-Sodsup2.hkl
Contains datablock Z-Sod

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616017071/ku3185Z-Amsup3.hkl
Contains datablock Z-Am

CCDC references: 1511352; 1511351

Computing details top

For both compounds, data collection: APEX2 (Bruker, 2014); cell refinement: APEX2 (Bruker, 2014); data reduction: APEX2 and SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Bruker, 1998) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and publCIF (Westrip, 2010).

(Z-Sod) Poly[[aqua(µ6-2-amino-6-oxo-3-nitro-1,6-dihydropyridinido)sodium]–6-amino-5-nitropyridin-2(1H)-one–water (1/1/1)] top
Crystal data top
[Na(C5H4N3O3)(H2O)]·C5H5N3O3·H2OF(000) = 760
Mr = 368.26Dx = 1.673 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 20.8644 (14) ÅCell parameters from 3013 reflections
b = 3.5981 (2) Åθ = 2.0–28.0°
c = 20.2402 (14) ŵ = 0.17 mm1
β = 105.8625 (13)°T = 100 K
V = 1461.61 (16) Å3Needle, yellow
Z = 40.40 × 0.05 × 0.03 mm
Data collection top
Bruker APEXII DUO
diffractometer
1329 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
phi and ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: analytical
(SADABS; Bruker, 2014)
h = 2426
Tmin = 0.964, Tmax = 0.997k = 44
7572 measured reflectionsl = 2626
1682 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: mixed
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.054P)2 + 0.3149P]
where P = (Fo2 + 2Fc2)/3
1682 reflections(Δ/σ)max < 0.001
133 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.23 e Å3
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.

Refinement. All H atoms bound to C atoms were positioned geometrically ( C—H = 0.93/1.00 Å) and allowed to ride with Uiso(H)= 1.2/1.5Ueq(C).

The asymmetric unit consists of the molecule, a water solvent molecule and a sodium ion located on an 2-fold rotational axis of symmetry. The molecule had a 50% occupancy H atom on the ring nitrogen N1. The molecules crystallize as dimers of neutral and anionic molecule where the ring nitrogen H atom spend half the time on one and the other half of the second molecule of the pair related by inversion symmetry. In addition to the strong hydrogen-bonding between H1a and N1 of the pair of the molecules, this type of dimer crystallization is also driven by the strong dual hydrogen-bonding between the imino protons of N3 and O1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Na10.00000.8127 (2)0.25000.0189 (2)
O10.33936 (5)0.5410 (3)0.09450 (5)0.0234 (3)
O20.08687 (5)0.7655 (3)0.18809 (5)0.0273 (3)
O30.04132 (5)0.5154 (3)0.08790 (5)0.0253 (3)
N10.22868 (6)0.4386 (3)0.05437 (5)0.0152 (3)
H1A0.2380 (16)0.350 (9)0.0244 (16)0.018*0.5
N20.09214 (6)0.6320 (3)0.13258 (5)0.0192 (3)
N30.11780 (6)0.3242 (4)0.00782 (5)0.0178 (3)
H3B0.1303 (9)0.223 (5)0.0240 (9)0.028 (5)*
H3C0.0751 (9)0.328 (6)0.0086 (9)0.032 (5)*
C10.28274 (7)0.5701 (4)0.10369 (6)0.0161 (3)
C20.27211 (7)0.7394 (4)0.16454 (6)0.0158 (3)
H2A0.30870.83960.19880.019*
C30.21023 (7)0.7547 (4)0.17251 (6)0.0159 (3)
H3A0.20340.86140.21300.019*
C40.15483 (7)0.6131 (4)0.12102 (6)0.0155 (3)
C50.16537 (7)0.4567 (4)0.05971 (6)0.0145 (3)
O40.45554 (5)0.8140 (3)0.17415 (5)0.0196 (2)
H4A0.4176 (11)0.754 (5)0.1513 (10)0.036 (5)*
H4B0.4778 (11)0.862 (7)0.1459 (12)0.057 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Na10.0211 (4)0.0186 (4)0.0173 (4)0.0000.0056 (3)0.000
O10.0165 (5)0.0351 (6)0.0188 (5)0.0039 (4)0.0052 (4)0.0082 (4)
O20.0272 (6)0.0364 (7)0.0231 (5)0.0015 (5)0.0149 (4)0.0097 (4)
O30.0173 (5)0.0368 (7)0.0222 (5)0.0036 (5)0.0061 (4)0.0048 (4)
N10.0164 (6)0.0173 (6)0.0120 (5)0.0008 (5)0.0040 (4)0.0010 (4)
N20.0220 (7)0.0196 (6)0.0180 (5)0.0002 (5)0.0088 (5)0.0010 (5)
N30.0153 (6)0.0244 (7)0.0144 (5)0.0023 (5)0.0050 (4)0.0043 (5)
C10.0184 (7)0.0158 (7)0.0140 (6)0.0004 (5)0.0043 (5)0.0026 (5)
C20.0197 (7)0.0150 (7)0.0108 (5)0.0025 (5)0.0011 (5)0.0005 (5)
C30.0243 (7)0.0128 (7)0.0112 (6)0.0010 (5)0.0058 (5)0.0001 (4)
C40.0184 (7)0.0137 (7)0.0154 (6)0.0001 (5)0.0066 (5)0.0002 (5)
C50.0177 (7)0.0122 (6)0.0139 (6)0.0009 (5)0.0049 (5)0.0024 (5)
O40.0163 (5)0.0258 (6)0.0158 (5)0.0031 (4)0.0029 (4)0.0014 (4)
Geometric parameters (Å, º) top
Na1—O4i2.3788 (12)N2—C41.3920 (17)
Na1—O4ii2.3788 (12)N3—C51.3212 (17)
Na1—O4iii2.3859 (12)N3—H3B0.841 (18)
Na1—O4iv2.3859 (12)N3—H3C0.895 (18)
Na1—O2v2.4749 (10)C1—C21.4445 (17)
Na1—O22.4749 (10)C2—C31.3454 (19)
Na1—Na1vi3.5981 (2)C2—H2A0.9500
Na1—Na1vii3.5981 (2)C3—C41.4224 (18)
O1—C11.2496 (16)C3—H3A0.9500
O2—N21.2542 (14)C4—C51.4331 (17)
O3—N21.2625 (15)O4—Na1viii2.3788 (12)
N1—C51.3559 (17)O4—Na1ix2.3859 (12)
N1—C11.3700 (17)O4—H4A0.83 (2)
N1—H1A0.76 (3)O4—H4B0.85 (2)
O4i—Na1—O4ii82.07 (6)C5—N1—H1A124 (2)
O4i—Na1—O4iii179.85 (4)C1—N1—H1A113 (2)
O4ii—Na1—O4iii98.08 (3)O2—N2—O3120.46 (11)
O4i—Na1—O4iv98.08 (3)O2—N2—C4119.07 (11)
O4ii—Na1—O4iv179.85 (4)O3—N2—C4120.47 (11)
O4iii—Na1—O4iv81.77 (5)C5—N3—H3B116.3 (12)
O4i—Na1—O2v93.71 (4)C5—N3—H3C121.0 (11)
O4ii—Na1—O2v80.32 (4)H3B—N3—H3C122.6 (16)
O4iii—Na1—O2v86.32 (4)O1—C1—N1119.09 (11)
O4iv—Na1—O2v99.66 (4)O1—C1—C2122.27 (12)
O4i—Na1—O280.32 (4)N1—C1—C2118.64 (12)
O4ii—Na1—O293.71 (4)C3—C2—C1119.69 (12)
O4iii—Na1—O299.66 (4)C3—C2—H2A120.2
O4iv—Na1—O286.32 (4)C1—C2—H2A120.2
O2v—Na1—O2172.14 (7)C2—C3—C4120.78 (11)
O4i—Na1—Na1vi138.96 (3)C2—C3—H3A119.6
O4ii—Na1—Na1vi138.96 (3)C4—C3—H3A119.6
O4iii—Na1—Na1vi40.89 (3)N2—C4—C3118.16 (11)
O4iv—Na1—Na1vi40.89 (3)N2—C4—C5122.57 (12)
O2v—Na1—Na1vi93.93 (3)C3—C4—C5119.27 (12)
O2—Na1—Na1vi93.93 (3)N3—C5—N1117.12 (11)
O4i—Na1—Na1vii41.04 (3)N3—C5—C4124.77 (12)
O4ii—Na1—Na1vii41.04 (3)N1—C5—C4118.11 (12)
O4iii—Na1—Na1vii139.11 (3)Na1viii—O4—Na1ix98.08 (3)
O4iv—Na1—Na1vii139.11 (3)Na1viii—O4—H4A134.4 (13)
O2v—Na1—Na1vii86.07 (3)Na1ix—O4—H4A107.9 (13)
O2—Na1—Na1vii86.07 (3)Na1viii—O4—H4B95.4 (16)
Na1vi—Na1—Na1vii180.0Na1ix—O4—H4B113.5 (16)
N2—O2—Na1137.35 (9)H4A—O4—H4B106.9 (19)
C5—N1—C1123.46 (11)
Symmetry codes: (i) x1/2, y1/2, z; (ii) x+1/2, y1/2, z+1/2; (iii) x+1/2, y+1/2, z+1/2; (iv) x1/2, y+1/2, z; (v) x, y, z+1/2; (vi) x, y+1, z; (vii) x, y1, z; (viii) x+1/2, y+1/2, z; (ix) x+1/2, y1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···N1x0.76 (3)2.17 (3)2.924 (2)174 (3)
N3—H3B···O1x0.841 (18)1.958 (18)2.7975 (15)176.5 (17)
N3—H3C···O30.895 (18)2.036 (18)2.6570 (15)125.4 (14)
O4—H4A···O10.83 (2)1.88 (2)2.7025 (14)169.2 (19)
O4—H4B···O2viii0.85 (2)2.64 (2)3.1313 (16)118.4 (18)
O4—H4B···O3viii0.85 (2)2.07 (2)2.9129 (14)172 (2)
Symmetry codes: (viii) x+1/2, y+1/2, z; (x) x+1/2, y+1/2, z.
(Z-Am) Ammonium 2-amino-6-oxo-3-nitro-1,6-dihydropyridinide–6-amino-5-nitropyridin-2(1H)-one–water (1/1/1) top
Crystal data top
C10H15N7O7F(000) = 360
Mr = 345.29Dx = 1.635 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 10.8724 (10) ÅCell parameters from 3888 reflections
b = 3.7149 (3) Åθ = 2.0–28.0°
c = 17.3901 (15) ŵ = 0.14 mm1
β = 93.012 (2)°T = 100 K
V = 701.41 (11) Å3Needle, yellow
Z = 20.29 × 0.09 × 0.07 mm
Data collection top
Bruker APEXII DUO
diffractometer
2934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
phi and ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: analytical
(SADABS; Bruker, 2014)
h = 1410
Tmin = 0.976, Tmax = 0.993k = 44
7278 measured reflectionsl = 2222
3174 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.090P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.004
3174 reflectionsΔρmax = 0.26 e Å3
248 parametersΔρmin = 0.22 e Å3
31 restraintsAbsolute structure: Flack x determined using 1135 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.0 (6)
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.

Refinement. All H atoms bound to C atoms were positioned geometrically ( C—H = 0.93/1.00 Å) and allowed to ride with Uiso(H)= 1.2/1.5Ueq(C). Methyl ones were allowed to rotate around the corresponding C—C.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O1A0.51782 (14)0.5944 (6)0.25542 (8)0.0287 (4)
O2A0.74782 (14)0.4261 (6)0.58249 (8)0.0277 (4)
O3A0.89863 (13)0.7106 (5)0.53151 (8)0.0229 (4)
N1A0.69744 (16)0.7205 (5)0.32140 (9)0.0168 (4)
H1A0.73020.76690.27960.020*0.5
N2A0.79419 (16)0.5702 (6)0.52580 (9)0.0184 (4)
N3A0.88118 (15)0.8778 (5)0.38244 (9)0.0164 (4)
H3A"0.90380.97090.33960.020*
H3A'0.93140.89000.42500.020*
C2A0.53538 (19)0.4210 (6)0.38606 (11)0.0182 (4)
H2A0.45690.32070.38480.022*
C1A0.58169 (18)0.5796 (7)0.31828 (11)0.0183 (4)
C3A0.60718 (18)0.4192 (6)0.45191 (11)0.0164 (4)
H3A0.57780.31440.49590.020*
C4A0.72559 (18)0.5732 (6)0.45506 (11)0.0149 (4)
C5A0.77185 (18)0.7266 (6)0.38711 (11)0.0139 (4)
O3B0.60860 (13)0.8425 (5)0.03922 (8)0.0200 (4)
O2B0.75985 (14)1.1212 (5)0.09095 (8)0.0217 (4)
O1B0.93970 (13)1.2439 (5)0.24812 (8)0.0215 (4)
N2B0.70885 (16)1.0112 (5)0.03188 (9)0.0158 (4)
N1B0.77706 (16)1.0180 (5)0.17746 (9)0.0158 (4)
H1B0.75250.95210.22110.019*0.5
N3B0.60902 (15)0.7782 (5)0.11268 (10)0.0172 (4)
H3B'0.56270.77080.06990.021*
H3B"0.57600.69390.15940.021*
C2B0.94121 (19)1.3154 (6)0.11296 (11)0.0165 (4)
H2B1.01701.43210.11510.020*
C1B0.88818 (19)1.1941 (6)0.18301 (11)0.0169 (4)
C4B0.76586 (18)1.0752 (6)0.03994 (10)0.0140 (4)
C3B0.88016 (19)1.2581 (6)0.04467 (11)0.0153 (4)
H3B0.91371.34030.00020.018*
C5B0.71398 (18)0.9528 (6)0.10969 (11)0.0136 (4)
O10.1624 (4)0.6432 (12)0.2800 (2)0.0205 (9)*0.5
O1'0.1591 (4)0.5247 (12)0.2800 (2)0.0196 (9)*0.5
H1C0.174 (4)0.584 (5)0.3259 (15)0.099 (11)*
H1D0.089 (3)0.597 (5)0.268 (2)0.099 (11)*
N20.3466 (5)0.1076 (12)0.2124 (2)0.0189 (8)*0.5
H10.337 (5)0.102 (14)0.157 (2)0.053 (10)*0.5
H20.386 (5)0.109 (13)0.233 (3)0.053 (10)*0.5
H30.270 (4)0.155 (13)0.236 (4)0.053 (10)*0.5
H40.410 (4)0.275 (15)0.230 (3)0.053 (10)*0.5
N2'0.2977 (5)0.0886 (13)0.2219 (2)0.0208 (9)*0.5
H1'0.292 (4)0.111 (17)0.1686 (18)0.039 (9)*0.5
H2'0.382 (3)0.095 (18)0.234 (3)0.039 (9)*0.5
H3'0.268 (4)0.274 (12)0.252 (3)0.039 (9)*0.5
H4'0.243 (4)0.098 (12)0.231 (2)0.039 (9)*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0156 (7)0.0539 (12)0.0166 (7)0.0042 (8)0.0002 (6)0.0035 (8)
O2A0.0267 (8)0.0404 (11)0.0163 (7)0.0017 (8)0.0047 (6)0.0113 (8)
O3A0.0166 (8)0.0334 (9)0.0184 (7)0.0004 (7)0.0021 (6)0.0011 (7)
N1A0.0152 (8)0.0215 (9)0.0137 (8)0.0011 (7)0.0023 (6)0.0039 (7)
N2A0.0184 (9)0.0213 (10)0.0158 (8)0.0047 (8)0.0033 (7)0.0028 (8)
N3A0.0146 (8)0.0225 (9)0.0123 (7)0.0024 (8)0.0014 (6)0.0017 (7)
C2A0.0142 (9)0.018 (1)0.0228 (10)0.0016 (9)0.0055 (8)0.0045 (9)
C1A0.015 (1)0.0240 (11)0.0158 (9)0.0043 (9)0.0011 (8)0.0045 (9)
C3A0.0194 (10)0.0131 (10)0.0173 (9)0.0011 (9)0.0071 (8)0.0011 (8)
C4A0.0161 (9)0.0152 (9)0.0135 (8)0.0037 (8)0.0024 (7)0.0006 (8)
C5A0.0144 (9)0.0118 (9)0.0156 (9)0.0024 (8)0.0024 (7)0.0013 (8)
O3B0.0177 (7)0.0248 (9)0.0173 (7)0.0007 (7)0.0030 (6)0.0005 (6)
O2B0.0250 (8)0.0297 (9)0.0108 (6)0.0030 (7)0.0043 (5)0.0020 (6)
O1B0.0197 (8)0.0287 (9)0.0160 (7)0.0025 (7)0.0008 (6)0.0010 (7)
N2B0.0176 (8)0.0159 (10)0.0139 (8)0.0042 (7)0.0014 (6)0.0005 (7)
N1B0.0163 (8)0.0191 (9)0.0119 (7)0.0019 (7)0.0010 (6)0.0005 (7)
N3B0.0150 (8)0.0211 (10)0.0154 (8)0.0015 (7)0.0001 (6)0.0018 (7)
C2B0.0149 (10)0.0144 (10)0.0204 (10)0.0006 (8)0.0039 (8)0.0001 (8)
C1B0.0173 (10)0.0175 (11)0.0159 (9)0.0052 (9)0.0006 (8)0.0003 (8)
C4B0.0163 (10)0.0133 (9)0.0123 (8)0.0025 (8)0.0009 (7)0.0007 (8)
C3B0.0177 (10)0.0139 (10)0.0148 (9)0.0029 (9)0.0054 (7)0.0015 (8)
C5B0.0134 (9)0.0117 (10)0.0156 (9)0.0039 (8)0.0004 (7)0.0005 (8)
Geometric parameters (Å, º) top
O1A—C1A1.265 (2)N1B—H1B0.8541
O2A—N2A1.251 (2)N3B—C5B1.316 (3)
O3A—N2A1.249 (2)N3B—H3B'0.8762
N1A—C1A1.361 (3)N3B—H3B"0.9588
N1A—C5A1.365 (2)C2B—C3B1.347 (3)
N1A—H1A0.8440C2B—C1B1.447 (3)
N2A—C4A1.405 (2)C2B—H2B0.9300
N3A—C5A1.321 (3)C4B—C3B1.415 (3)
N3A—H3A"0.8691C4B—C5B1.438 (3)
N3A—H3A'0.8972C3B—H3B0.9300
C2A—C3A1.352 (3)O1—H1C0.83 (2)
C2A—C1A1.433 (3)O1—H1D0.84 (2)
C2A—H2A0.9300O1'—H1C0.83 (2)
C3A—C4A1.407 (3)O1'—H1D0.83 (2)
C3A—H3A0.9300N2—H10.97 (3)
C4A—C5A1.427 (3)N2—H20.97 (3)
O3B—N2B1.258 (2)N2—H30.97 (3)
O2B—N2B1.261 (2)N2—H40.97 (3)
O1B—C1B1.250 (2)N2'—H1'0.93 (3)
N2B—C4B1.386 (2)N2'—H2'0.93 (3)
N1B—C5B1.354 (2)N2'—H3'0.93 (3)
N1B—C1B1.373 (3)N2'—H4'0.93 (3)
C1A—N1A—C5A123.07 (17)C5B—N3B—H3B"124.0
C1A—N1A—H1A118.4H3B'—N3B—H3B"119.0
C5A—N1A—H1A117.3C3B—C2B—C1B119.58 (19)
O3A—N2A—O2A121.23 (16)C3B—C2B—H2B120.2
O3A—N2A—C4A120.34 (16)C1B—C2B—H2B120.2
O2A—N2A—C4A118.43 (18)O1B—C1B—N1B119.01 (17)
C5A—N3A—H3A"121.2O1B—C1B—C2B122.48 (19)
C5A—N3A—H3A'118.8N1B—C1B—C2B118.51 (18)
H3A"—N3A—H3A'120.0N2B—C4B—C3B118.99 (17)
C3A—C2A—C1A119.13 (19)N2B—C4B—C5B121.96 (18)
C3A—C2A—H2A120.4C3B—C4B—C5B119.02 (17)
C1A—C2A—H2A120.4C2B—C3B—C4B121.18 (18)
O1A—C1A—N1A118.82 (18)C2B—C3B—H3B119.4
O1A—C1A—C2A121.88 (19)C4B—C3B—H3B119.4
N1A—C1A—C2A119.30 (17)N3B—C5B—N1B117.04 (17)
C2A—C3A—C4A121.17 (19)N3B—C5B—C4B124.65 (18)
C2A—C3A—H3A119.4N1B—C5B—C4B118.31 (17)
C4A—C3A—H3A119.4H1C—O1—H1D107 (3)
N2A—C4A—C3A118.26 (17)H1C—O1'—H1D107 (3)
N2A—C4A—C5A122.30 (18)H1—N2—H2112 (2)
C3A—C4A—C5A119.44 (17)H1—N2—H3113 (6)
N3A—C5A—N1A116.82 (17)H2—N2—H3112 (2)
N3A—C5A—C4A125.32 (18)H1—N2—H4112 (2)
N1A—C5A—C4A117.86 (17)H2—N2—H497 (5)
O3B—N2B—O2B119.65 (16)H3—N2—H4111 (2)
O3B—N2B—C4B121.41 (16)H1'—N2'—H2'102.9 (19)
O2B—N2B—C4B118.94 (17)H1'—N2'—H3'119 (6)
C5B—N1B—C1B123.38 (17)H2'—N2'—H3'102.9 (19)
C5B—N1B—H1B123.7H1'—N2'—H4'102.8 (19)
C1B—N1B—H1B112.9H2'—N2'—H4'128 (6)
C5B—N3B—H3B'116.3H3'—N2'—H4'102.6 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···N1B0.842.092.909 (2)163
N3A—H3A"···O1B0.871.942.805 (2)171
N3A—H3A···O3A0.902.022.663 (2)128
N3A—H3A···O3Ai0.902.293.020 (2)138
N1B—H1B···N1A0.852.062.909 (2)172
N3B—H3B···O3B0.882.012.652 (2)130
N3B—H3B···O3Bii0.882.493.087 (2)126
N3B—H3B"···O1A0.961.852.805 (2)172
O1—H1C···O2Aiii0.83 (2)2.18 (2)2.743 (4)125 (2)
O1—H1C···O2Aiii0.83 (2)2.18 (2)2.951 (4)154 (3)
O1—H1D···O1Biv0.84 (2)2.10 (2)2.869 (4)153 (2)
O1—H1D···O1Biv0.83 (2)2.10 (2)2.636 (4)122 (2)
N2—H1···O3Bii0.97 (3)2.33 (4)3.197 (4)148 (4)
N2—H1···O2Bv0.97 (3)2.34 (5)2.968 (5)122 (4)
N2—H1···N2Bii0.97 (3)2.68 (4)3.502 (4)144 (4)
N2—H2···O1Avi0.97 (3)1.84 (4)2.741 (5)154 (5)
N2—H3···O10.97 (3)2.31 (4)3.099 (6)138 (4)
N2—H4···O1A0.97 (3)1.71 (4)2.674 (5)175 (6)
N2—H1···O2Bv0.93 (3)2.32 (5)2.906 (5)121 (4)
N2—H2···O1A0.93 (3)2.39 (5)3.074 (5)130 (5)
N2—H3···O10.93 (3)1.61 (4)2.465 (6)152 (5)
N2—H4···O1vi0.93 (3)1.90 (3)2.800 (6)161 (4)
Symmetry codes: (i) x2, y+1/2, z1; (ii) x1, y1/2, z; (iii) x1, y+1/2, z1; (iv) x+1, y1, z; (v) x1, y3/2, z; (vi) x, y1, z.
A list of crystallization conditions. top
Solventb.p. (K)m.p (K)Solubility
DMSO462292++++ (dissolved all)
DMF427212++++ (dissolved all)
Water373273++++
Ethylene glycol470260+++ (white precipitate)
Ethanol195159++
Pyridine389231++
Acetonitrile354228++
Ethyl acetate350189+ (white precipitate)
Toluene384178-
Benzene353278.5-
DCM313176-
Diethyl ether308157-
THF339165-
Hexanes341179-
Chlorobenzene404228-
Chloroform334209-
tert-butyl methyl ether328164-
1,4-Dioxane374285-
 

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