Crystal structures of deprotonated nucleobases from an expanded DNA alphabet

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.

Computing details

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)]

Crystal data

[Na(C5H4N3O3)(H2O)]·C5H5N3O3·H2O	F(000) = 760
Mr = 368.26	Dx = 1.673 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.8644 (14) Å	Cell parameters from 3013 reflections
b = 3.5981 (2) Å	θ = 2.0–28.0°
c = 20.2402 (14) Å	µ = 0.17 mm^−1
β = 105.8625 (13)°	T = 100 K
V = 1461.61 (16) Å^3	Needle, yellow
Z = 4	0.40 × 0.05 × 0.03 mm

Data collection

Bruker APEXII DUO diffractometer	1329 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
phi and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: analytical (SADABS; Bruker, 2014)	h = −24→26
Tmin = 0.964, Tmax = 0.997	k = −4→4
7572 measured reflections	l = −26→26
1682 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: mixed
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.054P)^2 + 0.3149P] where P = (Fo^2 + 2Fc^2)/3
1682 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Na1	0.0000	0.8127 (2)	0.2500	0.0189 (2)
O1	0.33936 (5)	0.5410 (3)	0.09450 (5)	0.0234 (3)
O2	0.08687 (5)	0.7655 (3)	0.18809 (5)	0.0273 (3)
O3	0.04132 (5)	0.5154 (3)	0.08790 (5)	0.0253 (3)
N1	0.22868 (6)	0.4386 (3)	0.05437 (5)	0.0152 (3)
H1A	0.2380 (16)	0.350 (9)	0.0244 (16)	0.018*	0.5
N2	0.09214 (6)	0.6320 (3)	0.13258 (5)	0.0192 (3)
N3	0.11780 (6)	0.3242 (4)	0.00782 (5)	0.0178 (3)
H3B	0.1303 (9)	0.223 (5)	−0.0240 (9)	0.028 (5)*
H3C	0.0751 (9)	0.328 (6)	0.0086 (9)	0.032 (5)*
C1	0.28274 (7)	0.5701 (4)	0.10369 (6)	0.0161 (3)
C2	0.27211 (7)	0.7394 (4)	0.16454 (6)	0.0158 (3)
H2A	0.3087	0.8396	0.1988	0.019*
C3	0.21023 (7)	0.7547 (4)	0.17251 (6)	0.0159 (3)
H3A	0.2034	0.8614	0.2130	0.019*
C4	0.15483 (7)	0.6131 (4)	0.12102 (6)	0.0155 (3)
C5	0.16537 (7)	0.4567 (4)	0.05971 (6)	0.0145 (3)
O4	0.45554 (5)	0.8140 (3)	0.17415 (5)	0.0196 (2)
H4A	0.4176 (11)	0.754 (5)	0.1513 (10)	0.036 (5)*
H4B	0.4778 (11)	0.862 (7)	0.1459 (12)	0.057 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Na1	0.0211 (4)	0.0186 (4)	0.0173 (4)	0.000	0.0056 (3)	0.000
O1	0.0165 (5)	0.0351 (6)	0.0188 (5)	−0.0039 (4)	0.0052 (4)	−0.0082 (4)
O2	0.0272 (6)	0.0364 (7)	0.0231 (5)	−0.0015 (5)	0.0149 (4)	−0.0097 (4)
O3	0.0173 (5)	0.0368 (7)	0.0222 (5)	−0.0036 (5)	0.0061 (4)	−0.0048 (4)
N1	0.0164 (6)	0.0173 (6)	0.0120 (5)	−0.0008 (5)	0.0040 (4)	−0.0010 (4)
N2	0.0220 (7)	0.0196 (6)	0.0180 (5)	−0.0002 (5)	0.0088 (5)	−0.0010 (5)
N3	0.0153 (6)	0.0244 (7)	0.0144 (5)	−0.0023 (5)	0.0050 (4)	−0.0043 (5)
C1	0.0184 (7)	0.0158 (7)	0.0140 (6)	−0.0004 (5)	0.0043 (5)	0.0026 (5)
C2	0.0197 (7)	0.0150 (7)	0.0108 (5)	−0.0025 (5)	0.0011 (5)	−0.0005 (5)
C3	0.0243 (7)	0.0128 (7)	0.0112 (6)	0.0010 (5)	0.0058 (5)	0.0001 (4)
C4	0.0184 (7)	0.0137 (7)	0.0154 (6)	−0.0001 (5)	0.0066 (5)	0.0002 (5)
C5	0.0177 (7)	0.0122 (6)	0.0139 (6)	0.0009 (5)	0.0049 (5)	0.0024 (5)
O4	0.0163 (5)	0.0258 (6)	0.0158 (5)	−0.0031 (4)	0.0029 (4)	−0.0014 (4)

Geometric parameters (Å, º)

Na1—O4^i	2.3788 (12)	N2—C4	1.3920 (17)
Na1—O4^ii	2.3788 (12)	N3—C5	1.3212 (17)
Na1—O4^iii	2.3859 (12)	N3—H3B	0.841 (18)
Na1—O4^iv	2.3859 (12)	N3—H3C	0.895 (18)
Na1—O2^v	2.4749 (10)	C1—C2	1.4445 (17)
Na1—O2	2.4749 (10)	C2—C3	1.3454 (19)
Na1—Na1^vi	3.5981 (2)	C2—H2A	0.9500
Na1—Na1^vii	3.5981 (2)	C3—C4	1.4224 (18)
O1—C1	1.2496 (16)	C3—H3A	0.9500
O2—N2	1.2542 (14)	C4—C5	1.4331 (17)
O3—N2	1.2625 (15)	O4—Na1^viii	2.3788 (12)
N1—C5	1.3559 (17)	O4—Na1^ix	2.3859 (12)
N1—C1	1.3700 (17)	O4—H4A	0.83 (2)
N1—H1A	0.76 (3)	O4—H4B	0.85 (2)
O4^i—Na1—O4^ii	82.07 (6)	C5—N1—H1A	124 (2)
O4^i—Na1—O4^iii	179.85 (4)	C1—N1—H1A	113 (2)
O4^ii—Na1—O4^iii	98.08 (3)	O2—N2—O3	120.46 (11)
O4^i—Na1—O4^iv	98.08 (3)	O2—N2—C4	119.07 (11)
O4^ii—Na1—O4^iv	179.85 (4)	O3—N2—C4	120.47 (11)
O4^iii—Na1—O4^iv	81.77 (5)	C5—N3—H3B	116.3 (12)
O4^i—Na1—O2^v	93.71 (4)	C5—N3—H3C	121.0 (11)
O4^ii—Na1—O2^v	80.32 (4)	H3B—N3—H3C	122.6 (16)
O4^iii—Na1—O2^v	86.32 (4)	O1—C1—N1	119.09 (11)
O4^iv—Na1—O2^v	99.66 (4)	O1—C1—C2	122.27 (12)
O4^i—Na1—O2	80.32 (4)	N1—C1—C2	118.64 (12)
O4^ii—Na1—O2	93.71 (4)	C3—C2—C1	119.69 (12)
O4^iii—Na1—O2	99.66 (4)	C3—C2—H2A	120.2
O4^iv—Na1—O2	86.32 (4)	C1—C2—H2A	120.2
O2^v—Na1—O2	172.14 (7)	C2—C3—C4	120.78 (11)
O4^i—Na1—Na1^vi	138.96 (3)	C2—C3—H3A	119.6
O4^ii—Na1—Na1^vi	138.96 (3)	C4—C3—H3A	119.6
O4^iii—Na1—Na1^vi	40.89 (3)	N2—C4—C3	118.16 (11)
O4^iv—Na1—Na1^vi	40.89 (3)	N2—C4—C5	122.57 (12)
O2^v—Na1—Na1^vi	93.93 (3)	C3—C4—C5	119.27 (12)
O2—Na1—Na1^vi	93.93 (3)	N3—C5—N1	117.12 (11)
O4^i—Na1—Na1^vii	41.04 (3)	N3—C5—C4	124.77 (12)
O4^ii—Na1—Na1^vii	41.04 (3)	N1—C5—C4	118.11 (12)
O4^iii—Na1—Na1^vii	139.11 (3)	Na1^viii—O4—Na1^ix	98.08 (3)
O4^iv—Na1—Na1^vii	139.11 (3)	Na1^viii—O4—H4A	134.4 (13)
O2^v—Na1—Na1^vii	86.07 (3)	Na1^ix—O4—H4A	107.9 (13)
O2—Na1—Na1^vii	86.07 (3)	Na1^viii—O4—H4B	95.4 (16)
Na1^vi—Na1—Na1^vii	180.0	Na1^ix—O4—H4B	113.5 (16)
N2—O2—Na1	137.35 (9)	H4A—O4—H4B	106.9 (19)
C5—N1—C1	123.46 (11)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N1^x	0.76 (3)	2.17 (3)	2.924 (2)	174 (3)
N3—H3B···O1^x	0.841 (18)	1.958 (18)	2.7975 (15)	176.5 (17)
N3—H3C···O3	0.895 (18)	2.036 (18)	2.6570 (15)	125.4 (14)
O4—H4A···O1	0.83 (2)	1.88 (2)	2.7025 (14)	169.2 (19)
O4—H4B···O2^viii	0.85 (2)	2.64 (2)	3.1313 (16)	118.4 (18)
O4—H4B···O3^viii	0.85 (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)

Crystal data

C10H15N7O7	F(000) = 360
Mr = 345.29	Dx = 1.635 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.8724 (10) Å	Cell parameters from 3888 reflections
b = 3.7149 (3) Å	θ = 2.0–28.0°
c = 17.3901 (15) Å	µ = 0.14 mm^−1
β = 93.012 (2)°	T = 100 K
V = 701.41 (11) Å^3	Needle, yellow
Z = 2	0.29 × 0.09 × 0.07 mm

Data collection

Bruker APEXII DUO diffractometer	2934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
phi and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: analytical (SADABS; Bruker, 2014)	h = −14→10
Tmin = 0.976, Tmax = 0.993	k = −4→4
7278 measured reflections	l = −22→22
3174 independent 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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.090P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.004
3174 reflections	Δρmax = 0.26 e Å^−3
248 parameters	Δρmin = −0.22 e Å^−3
31 restraints	Absolute structure: Flack x determined using 1135 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.0 (6)

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.

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

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1A	−0.51782 (14)	0.5944 (6)	−0.25542 (8)	0.0287 (4)
O2A	−0.74782 (14)	0.4261 (6)	−0.58249 (8)	0.0277 (4)
O3A	−0.89863 (13)	0.7106 (5)	−0.53151 (8)	0.0229 (4)
N1A	−0.69744 (16)	0.7205 (5)	−0.32140 (9)	0.0168 (4)
H1A	−0.7302	0.7669	−0.2796	0.020*	0.5
N2A	−0.79419 (16)	0.5702 (6)	−0.52580 (9)	0.0184 (4)
N3A	−0.88118 (15)	0.8778 (5)	−0.38244 (9)	0.0164 (4)
H3A"	−0.9038	0.9709	−0.3396	0.020*
H3A'	−0.9314	0.8900	−0.4250	0.020*
C2A	−0.53538 (19)	0.4210 (6)	−0.38606 (11)	0.0182 (4)
H2A	−0.4569	0.3207	−0.3848	0.022*
C1A	−0.58169 (18)	0.5796 (7)	−0.31828 (11)	0.0183 (4)
C3A	−0.60718 (18)	0.4192 (6)	−0.45191 (11)	0.0164 (4)
H3A	−0.5778	0.3144	−0.4959	0.020*
C4A	−0.72559 (18)	0.5732 (6)	−0.45506 (11)	0.0149 (4)
C5A	−0.77185 (18)	0.7266 (6)	−0.38711 (11)	0.0139 (4)
O3B	−0.60860 (13)	0.8425 (5)	0.03922 (8)	0.0200 (4)
O2B	−0.75985 (14)	1.1212 (5)	0.09095 (8)	0.0217 (4)
O1B	−0.93970 (13)	1.2439 (5)	−0.24812 (8)	0.0215 (4)
N2B	−0.70885 (16)	1.0112 (5)	0.03188 (9)	0.0158 (4)
N1B	−0.77706 (16)	1.0180 (5)	−0.17746 (9)	0.0158 (4)
H1B	−0.7525	0.9521	−0.2211	0.019*	0.5
N3B	−0.60902 (15)	0.7782 (5)	−0.11268 (10)	0.0172 (4)
H3B'	−0.5627	0.7708	−0.0699	0.021*
H3B"	−0.5760	0.6939	−0.1594	0.021*
C2B	−0.94121 (19)	1.3154 (6)	−0.11296 (11)	0.0165 (4)
H2B	−1.0170	1.4321	−0.1151	0.020*
C1B	−0.88818 (19)	1.1941 (6)	−0.18301 (11)	0.0169 (4)
C4B	−0.76586 (18)	1.0752 (6)	−0.03994 (10)	0.0140 (4)
C3B	−0.88016 (19)	1.2581 (6)	−0.04467 (11)	0.0153 (4)
H3B	−0.9137	1.3403	0.0002	0.018*
C5B	−0.71398 (18)	0.9528 (6)	−0.10969 (11)	0.0136 (4)
O1	−0.1624 (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
H1C	−0.174 (4)	0.584 (5)	−0.3259 (15)	0.099 (11)*
H1D	−0.089 (3)	0.597 (5)	−0.268 (2)	0.099 (11)*
N2	−0.3466 (5)	0.1076 (12)	−0.2124 (2)	0.0189 (8)*	0.5
H1	−0.337 (5)	0.102 (14)	−0.157 (2)	0.053 (10)*	0.5
H2	−0.386 (5)	−0.109 (13)	−0.233 (3)	0.053 (10)*	0.5
H3	−0.270 (4)	0.155 (13)	−0.236 (4)	0.053 (10)*	0.5
H4	−0.410 (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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0156 (7)	0.0539 (12)	0.0166 (7)	0.0042 (8)	0.0002 (6)	0.0035 (8)
O2A	0.0267 (8)	0.0404 (11)	0.0163 (7)	−0.0017 (8)	0.0047 (6)	−0.0113 (8)
O3A	0.0166 (8)	0.0334 (9)	0.0184 (7)	0.0004 (7)	−0.0021 (6)	−0.0011 (7)
N1A	0.0152 (8)	0.0215 (9)	0.0137 (8)	−0.0011 (7)	0.0023 (6)	0.0039 (7)
N2A	0.0184 (9)	0.0213 (10)	0.0158 (8)	−0.0047 (8)	0.0033 (7)	−0.0028 (8)
N3A	0.0146 (8)	0.0225 (9)	0.0123 (7)	0.0024 (8)	0.0014 (6)	−0.0017 (7)
C2A	0.0142 (9)	0.018 (1)	0.0228 (10)	0.0016 (9)	0.0055 (8)	0.0045 (9)
C1A	0.015 (1)	0.0240 (11)	0.0158 (9)	−0.0043 (9)	0.0011 (8)	0.0045 (9)
C3A	0.0194 (10)	0.0131 (10)	0.0173 (9)	−0.0011 (9)	0.0071 (8)	−0.0011 (8)
C4A	0.0161 (9)	0.0152 (9)	0.0135 (8)	−0.0037 (8)	0.0024 (7)	0.0006 (8)
C5A	0.0144 (9)	0.0118 (9)	0.0156 (9)	−0.0024 (8)	0.0024 (7)	0.0013 (8)
O3B	0.0177 (7)	0.0248 (9)	0.0173 (7)	0.0007 (7)	−0.0030 (6)	0.0005 (6)
O2B	0.0250 (8)	0.0297 (9)	0.0108 (6)	−0.0030 (7)	0.0043 (5)	−0.0020 (6)
O1B	0.0197 (8)	0.0287 (9)	0.0160 (7)	0.0025 (7)	−0.0008 (6)	0.0010 (7)
N2B	0.0176 (8)	0.0159 (10)	0.0139 (8)	−0.0042 (7)	0.0014 (6)	−0.0005 (7)
N1B	0.0163 (8)	0.0191 (9)	0.0119 (7)	−0.0019 (7)	0.0010 (6)	0.0005 (7)
N3B	0.0150 (8)	0.0211 (10)	0.0154 (8)	0.0015 (7)	0.0001 (6)	−0.0018 (7)
C2B	0.0149 (10)	0.0144 (10)	0.0204 (10)	0.0006 (8)	0.0039 (8)	−0.0001 (8)
C1B	0.0173 (10)	0.0175 (11)	0.0159 (9)	−0.0052 (9)	0.0006 (8)	0.0003 (8)
C4B	0.0163 (10)	0.0133 (9)	0.0123 (8)	−0.0025 (8)	0.0009 (7)	0.0007 (8)
C3B	0.0177 (10)	0.0139 (10)	0.0148 (9)	−0.0029 (9)	0.0054 (7)	−0.0015 (8)
C5B	0.0134 (9)	0.0117 (10)	0.0156 (9)	−0.0039 (8)	0.0004 (7)	0.0005 (8)

Geometric parameters (Å, º)

O1A—C1A	1.265 (2)	N1B—H1B	0.8541
O2A—N2A	1.251 (2)	N3B—C5B	1.316 (3)
O3A—N2A	1.249 (2)	N3B—H3B'	0.8762
N1A—C1A	1.361 (3)	N3B—H3B"	0.9588
N1A—C5A	1.365 (2)	C2B—C3B	1.347 (3)
N1A—H1A	0.8440	C2B—C1B	1.447 (3)
N2A—C4A	1.405 (2)	C2B—H2B	0.9300
N3A—C5A	1.321 (3)	C4B—C3B	1.415 (3)
N3A—H3A"	0.8691	C4B—C5B	1.438 (3)
N3A—H3A'	0.8972	C3B—H3B	0.9300
C2A—C3A	1.352 (3)	O1—H1C	0.83 (2)
C2A—C1A	1.433 (3)	O1—H1D	0.84 (2)
C2A—H2A	0.9300	O1'—H1C	0.83 (2)
C3A—C4A	1.407 (3)	O1'—H1D	0.83 (2)
C3A—H3A	0.9300	N2—H1	0.97 (3)
C4A—C5A	1.427 (3)	N2—H2	0.97 (3)
O3B—N2B	1.258 (2)	N2—H3	0.97 (3)
O2B—N2B	1.261 (2)	N2—H4	0.97 (3)
O1B—C1B	1.250 (2)	N2'—H1'	0.93 (3)
N2B—C4B	1.386 (2)	N2'—H2'	0.93 (3)
N1B—C5B	1.354 (2)	N2'—H3'	0.93 (3)
N1B—C1B	1.373 (3)	N2'—H4'	0.93 (3)
C1A—N1A—C5A	123.07 (17)	C5B—N3B—H3B"	124.0
C1A—N1A—H1A	118.4	H3B'—N3B—H3B"	119.0
C5A—N1A—H1A	117.3	C3B—C2B—C1B	119.58 (19)
O3A—N2A—O2A	121.23 (16)	C3B—C2B—H2B	120.2
O3A—N2A—C4A	120.34 (16)	C1B—C2B—H2B	120.2
O2A—N2A—C4A	118.43 (18)	O1B—C1B—N1B	119.01 (17)
C5A—N3A—H3A"	121.2	O1B—C1B—C2B	122.48 (19)
C5A—N3A—H3A'	118.8	N1B—C1B—C2B	118.51 (18)
H3A"—N3A—H3A'	120.0	N2B—C4B—C3B	118.99 (17)
C3A—C2A—C1A	119.13 (19)	N2B—C4B—C5B	121.96 (18)
C3A—C2A—H2A	120.4	C3B—C4B—C5B	119.02 (17)
C1A—C2A—H2A	120.4	C2B—C3B—C4B	121.18 (18)
O1A—C1A—N1A	118.82 (18)	C2B—C3B—H3B	119.4
O1A—C1A—C2A	121.88 (19)	C4B—C3B—H3B	119.4
N1A—C1A—C2A	119.30 (17)	N3B—C5B—N1B	117.04 (17)
C2A—C3A—C4A	121.17 (19)	N3B—C5B—C4B	124.65 (18)
C2A—C3A—H3A	119.4	N1B—C5B—C4B	118.31 (17)
C4A—C3A—H3A	119.4	H1C—O1—H1D	107 (3)
N2A—C4A—C3A	118.26 (17)	H1C—O1'—H1D	107 (3)
N2A—C4A—C5A	122.30 (18)	H1—N2—H2	112 (2)
C3A—C4A—C5A	119.44 (17)	H1—N2—H3	113 (6)
N3A—C5A—N1A	116.82 (17)	H2—N2—H3	112 (2)
N3A—C5A—C4A	125.32 (18)	H1—N2—H4	112 (2)
N1A—C5A—C4A	117.86 (17)	H2—N2—H4	97 (5)
O3B—N2B—O2B	119.65 (16)	H3—N2—H4	111 (2)
O3B—N2B—C4B	121.41 (16)	H1'—N2'—H2'	102.9 (19)
O2B—N2B—C4B	118.94 (17)	H1'—N2'—H3'	119 (6)
C5B—N1B—C1B	123.38 (17)	H2'—N2'—H3'	102.9 (19)
C5B—N1B—H1B	123.7	H1'—N2'—H4'	102.8 (19)
C1B—N1B—H1B	112.9	H2'—N2'—H4'	128 (6)
C5B—N3B—H3B'	116.3	H3'—N2'—H4'	102.6 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N1B	0.84	2.09	2.909 (2)	163
N3A—H3A"···O1B	0.87	1.94	2.805 (2)	171
N3A—H3A′···O3A	0.90	2.02	2.663 (2)	128
N3A—H3A′···O3A^i	0.90	2.29	3.020 (2)	138
N1B—H1B···N1A	0.85	2.06	2.909 (2)	172
N3B—H3B′···O3B	0.88	2.01	2.652 (2)	130
N3B—H3B′···O3B^ii	0.88	2.49	3.087 (2)	126
N3B—H3B"···O1A	0.96	1.85	2.805 (2)	172
O1—H1C···O2A^iii	0.83 (2)	2.18 (2)	2.743 (4)	125 (2)
O1′—H1C···O2A^iii	0.83 (2)	2.18 (2)	2.951 (4)	154 (3)
O1—H1D···O1B^iv	0.84 (2)	2.10 (2)	2.869 (4)	153 (2)
O1′—H1D···O1B^iv	0.83 (2)	2.10 (2)	2.636 (4)	122 (2)
N2—H1···O3B^ii	0.97 (3)	2.33 (4)	3.197 (4)	148 (4)
N2—H1···O2B^v	0.97 (3)	2.34 (5)	2.968 (5)	122 (4)
N2—H1···N2B^ii	0.97 (3)	2.68 (4)	3.502 (4)	144 (4)
N2—H2···O1A^vi	0.97 (3)	1.84 (4)	2.741 (5)	154 (5)
N2—H3···O1	0.97 (3)	2.31 (4)	3.099 (6)	138 (4)
N2—H4···O1A	0.97 (3)	1.71 (4)	2.674 (5)	175 (6)
N2′—H1′···O2B^v	0.93 (3)	2.32 (5)	2.906 (5)	121 (4)
N2′—H2′···O1A	0.93 (3)	2.39 (5)	3.074 (5)	130 (5)
N2′—H3′···O1′	0.93 (3)	1.61 (4)	2.465 (6)	152 (5)
N2′—H4′···O1′^vi	0.93 (3)	1.90 (3)	2.800 (6)	161 (4)

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