Two isomeric di­deoxy­nucleosides

Swenson, D.C.; Nair, V.; Bera, S.

doi:10.1107/S0108270100008921

Two isomeric dideoxynucleosides

We have synthesized two isomeric dideoxynucleosides. 4(S)-(6-Amino-9H-purin-9-yl)-3-methylene-2,3,4,5-tetrahydrofuran-2(S)-ylmethanol, C₁₁H₁₃N₅O₂, is an analogue of the anti-HIV compound (S,S)-isodideoxyadenosine (isoDDA) with an exocyclic methylene group and is found to be anti-HIV inactive. The solid-state comformation is very similar to that of isoDDA. 4(S)-(6-Amino-3H-purin-3-yl)-3-methylene-2,3,4,5-tetrahydrofuran-2(S)-ylmethanol, C₁₁H₁₃N₅O₂, has an isomeric arrangement of the carbohydrate and base moieties, as confirmed by the crystal structure analysis. The asymmetric unit contains two independent molecules that differ in conformations at the sugar moiety.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100008921/qa0334sup1.cif Contains datablocks global, I, II
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008921/qa0334Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100008921/qa0334IIsup3.hkl Contains datablock II

CCDC references: 150388; 150389

Comment top

4(S)-6-Amino-9H-purin-9-yl)tetrahydro-2(S)-furanmethanol [(S,S)-isodideoxyadenosine or isoDDA; Bolon et al., 1994] has potent anti-HIV activity against HIV-1 and HIV-2 (Nair et al., 1995). Our interest in this compound led to the design and synthesis (using the Mitsunobu reaction as the key step) of compound (I), which was characterized by NMR, UV and HRMS data. Surprisingly compound (I) was found to be anti-HIV inactive from in vitro studies with infected CEM-SS cells. We determined the crystal structure in a search for possible explanations of the inactivity.

The solid-state conformation of compound (I) shows the sugar ring to have a O1'-envelope conformation anti to the adenine. This conformation is very similar to the solid-state comformation of isoDDA, the only difference being the O1',C5'-half-chair conformation of the sugar ring of isoDDA. In both compounds, an intramolecular hydrogen-bond-like interaction is present between H8 of adenine and O6' of the sugar moiety [C8—O6' = 3.261 (2) Å for isoDDA and 3.444 (2) Å for compound (I)]. The methylene substituent of compound (I) may impart sufficient conformational rigidity to the sugar ring to preserve this conformation in solution, thus preventing cellular phosphorylation which is a requirement for anti-HIV activity.

Intermolecular hydrogen bonding occurs between the N6 amine and O6' hydroxyl H atoms and the ring N atoms of the adenine moiety of adjacent molecules forming interlocked chains two molecules wide along the c axis.

The novel isomer, compound (II), has the sugar ring attachment at N3 of the base and has methylene substitution at C3'. The key step in the synthesis was a Mitsunobu coupling reaction. The title compound was characterized by NMR, UV and HRMS data. The crystal structure confirms the structure of the isomer.

The asymmetric unit contains two independent molecules (A and B) that have different carbohydrate-ring conformations. The conformations differ in three respects: (i) the ring of molecule A has an O5'A-envelope conformation, while the ring of molecule B has an O1'B,C5'B-half-chair conformation; (ii) in molecule A, the O6'A atom is anti to C3'A [C3'A—C2'A—C6'A—O6'A = −167.2 (4)°] and in molecule B, the O6'B atom is anti to H2'B [H2'B—C2'B—C6'B—O6'B = 173°]; (iii) the molecules differ in the relative orientation of the carbohydrate ring to the base; molecule A, C2A—N3A—C4'A—C5'A = 39.3 (6)°, and molecule B, C2B—N3B—C4'B—C5'B = 24.0 (6)°.

The hydrogen bonds between the amine H atoms and the ring N atoms of adjacent molecules form doubly linked ribbons of molecules parallel to the a axis. The O6' hydroxyl H atoms form hydrogen bonds that link the ribbons.

Experimental top

Preparation of compound (I): to a suspension of 2-(S)-(tert-butyldiphenylsilyloxymethyl)-3-methylenetetrahydrofuran-4-(R)-ol (1.66 mmol), Ph₃P (0.65 g) and adenine in dioxane (80 ml) at room temperature, DEAD (0.4 ml) was added dropwise and the resulting solution was stirred at room temperature for 22 h. The solvent was evaporated and the residue was purified on a silica-gel column. The major product (N-9 isomer; 0.34 g, 42% yield) was deprotected with NH₄F (0.4 g) in MeOH (30 ml) to give, after chromatographic separation on silica gel, compound (I) in 85% yield. Compound (I) crystallized from MeOH as white prisms: m.p. 463 K; ¹H NMR (DMSO-d₆) δ 8.15 (2 x s, 2H, H-2 and H-8), 7.25 (bs, 2H, NH₂), 5.56 (t, 1H, H-4'), 5.30 (bs, 1H, vinyl), 5.06 (t, J = 5.6 Hz, 1H, –OH), 4.44 (bs, 1H, H-2'), 3.73 (m, 2H, H-5'), 3.31 (t, J = 6.7 Hz, 2H, CH₂); UV (MeOH) λ_max 260.6 nm (ε 14000). HRMS (FAB): (M+Na)⁺ calculated for C₁₁H₁₃N₅NaO₂ 270.0966, found 270.0959. Preparation of the compound (II): to a suspension of 2-(S)-(tert-butyldiphenylsilyloxymethyl)-3-methylene-tetrahydrofuran-4-(R)-ol (1.66 mmol), Ph₃P (0.65 g), and adenine in dioxane (80 ml) at room temperature, DEAD (0.4 ml) was added dropwise and the reaction mixture was stirred at room temperature for 22 h. The solvent was then evaporated and the residue was separated on a silica-gel column. The minor product (N-3 isomer; 0.15 g, 19% yield) was deprotected with NH₄F to give, after chromatographic purification on silica gel, the compound (II) in 86% yield. The title compound crystallized from methanol as white prisms: m.p. 529 K; ¹H NMR (CD₃OD) δ 8.62 (s, 1H, H-8), 7.90 (s, 1H, H-2), 5.85 (m, iH, H-4'), 5.49 (m, 2H, vinyl), 4.52 (bs, 1H, H-2'), 4.29 (dd, J = 2.7, 10.6 Hz, 1H, H-5'a), 4.22 (dd, J = 5.9,10.6 Hz, 1H, H-5'b), 4.00 (dd, J = 2.9, 12.5 Hz, 1H, one of CH₂), 3.90 (dd, J = 3.3, 12.4 Hz, 1H, one H of CH₂); UV (MeOH) λ_max 274.5 nm (ε 13300); HMRS (FAB): (M + Na)⁺ calculated for C₁₁H₁₃N₅NaO₂ 270.0966, found 270.0954.

Computing details top

For both compounds, data collection: CAD-4 Operations Manual (Enraf-Nonius,1977); cell refinement: CAD-4 Operations Manual; data reduction: MolEN (Fair,1990); program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

C₁₁H₁₃N₅O₂	D_x = 1.429 Mg m⁻³
M_r = 247.26	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 24 reflections
a = 9.727 (2) Å	θ = 12.1–17.5°
b = 16.632 (4) Å	µ = 0.10 mm⁻¹
c = 7.104 (2) Å	T = 210 K
V = 1149.3 (5) Å³	Prism, colourless
Z = 4	0.36 × 0.24 × 0.21 mm
F(000) = 520

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.024
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.0°
Graphite monochromator	h = −11→11
θ–2θ scans	k = −1→19
4469 measured reflections	l = −8→8
1193 independent reflections	4 standard reflections every 120 min
1133 reflections with I > 2σ(I)	intensity decay: <2%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H-atom parameters constrained
wR(F²) = 0.064	w = 1/[σ²(F_o²) + (0.0349P)² + 0.1889P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.008
1193 reflections	Δρ_max = 0.17 e Å⁻³
166 parameters	Δρ_min = −0.10 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (3)

Crystal data top

C₁₁H₁₃N₅O₂	V = 1149.3 (5) Å³
M_r = 247.26	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.727 (2) Å	µ = 0.10 mm⁻¹
b = 16.632 (4) Å	T = 210 K
c = 7.104 (2) Å	0.36 × 0.24 × 0.21 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.024
4469 measured reflections	4 standard reflections every 120 min
1193 independent reflections	intensity decay: <2%
1133 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.023	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.11	Δρ_max = 0.17 e Å⁻³
1193 reflections	Δρ_min = −0.10 e Å⁻³
166 parameters

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
N1	0.58625 (15)	0.93347 (8)	0.7844 (2)	0.0263 (3)
C2	0.51904 (18)	0.86504 (10)	0.8226 (2)	0.0283 (4)
H2	0.4660	0.8657	0.9315	0.034*
N3	0.51725 (15)	0.79598 (8)	0.7266 (2)	0.0270 (3)
C4	0.59144 (16)	0.80265 (9)	0.5669 (2)	0.0216 (3)
C5	0.66519 (17)	0.86903 (9)	0.5073 (2)	0.0217 (4)
C6	0.66393 (18)	0.93680 (10)	0.6265 (2)	0.0236 (4)
N6	0.73670 (17)	1.00338 (9)	0.5930 (2)	0.0294 (3)
H6B	0.7335	1.0429	0.6710	0.035*
H6A	0.7867	1.0067	0.4935	0.035*
N7	0.73282 (15)	0.85309 (8)	0.3395 (2)	0.0252 (3)
C8	0.69869 (17)	0.77840 (10)	0.3012 (2)	0.0262 (4)
H8	0.7293	0.7512	0.1947	0.031*
N9	0.61379 (14)	0.74447 (8)	0.43286 (19)	0.0235 (3)
O1'	0.70105 (12)	0.57710 (7)	0.25746 (18)	0.0293 (3)
C2'	0.57703 (18)	0.57818 (10)	0.1480 (2)	0.0248 (4)
H2'	0.5278	0.5273	0.1657	0.030*
C3'	0.49360 (17)	0.64604 (10)	0.2329 (2)	0.0232 (4)
C4'	0.55393 (18)	0.66314 (9)	0.4263 (2)	0.0243 (4)
H4'	0.4831	0.6573	0.5235	0.029*
C5'	0.6618 (2)	0.59661 (10)	0.4460 (2)	0.0305 (4)
H5'B	0.7404	0.6155	0.5175	0.037*
H5'A	0.6232	0.5500	0.5089	0.037*
C6'	0.6127 (2)	0.58823 (11)	−0.0591 (2)	0.0293 (4)
H6'B	0.6746	0.5453	−0.0963	0.035*
H6'A	0.5294	0.5830	−0.1332	0.035*
O6'	0.67537 (14)	0.66326 (8)	−0.10049 (19)	0.0331 (3)
H6'	0.6158	0.6964	−0.1260	0.050 (7)*
C7'	0.39301 (18)	0.68600 (11)	0.1517 (3)	0.0327 (4)
H7'B	0.3667	0.6734	0.0294	0.039*
H7'A	0.3482	0.7269	0.2167	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0311 (7)	0.0245 (7)	0.0234 (7)	−0.0002 (6)	−0.0004 (7)	−0.0020 (6)
C2	0.0309 (8)	0.0285 (9)	0.0254 (9)	−0.0017 (7)	0.0050 (8)	−0.0022 (8)
N3	0.0311 (7)	0.0244 (7)	0.0255 (7)	−0.0029 (6)	0.0051 (6)	−0.0011 (6)
C4	0.0230 (8)	0.0202 (8)	0.0216 (8)	0.0016 (6)	−0.0027 (7)	−0.0002 (6)
C5	0.0227 (8)	0.0198 (8)	0.0228 (8)	0.0012 (6)	−0.0027 (7)	0.0015 (7)
C6	0.0258 (8)	0.0210 (8)	0.0239 (8)	0.0012 (7)	−0.0045 (7)	0.0018 (7)
N6	0.0432 (8)	0.0210 (6)	0.0241 (7)	−0.0063 (6)	0.0034 (7)	−0.0031 (6)
N7	0.0298 (7)	0.0214 (6)	0.0246 (7)	−0.0035 (6)	0.0020 (6)	0.0001 (6)
C8	0.0289 (9)	0.0258 (8)	0.0240 (8)	−0.0026 (7)	0.0035 (7)	−0.0012 (7)
N9	0.0278 (7)	0.0190 (7)	0.0236 (7)	−0.0019 (6)	0.0022 (6)	−0.0023 (6)
O1'	0.0329 (7)	0.0295 (6)	0.0254 (6)	0.0080 (5)	−0.0006 (5)	−0.0001 (5)
C2'	0.0297 (8)	0.0187 (7)	0.0260 (8)	−0.0019 (7)	−0.0001 (7)	0.0001 (7)
C3'	0.0239 (8)	0.0194 (7)	0.0262 (8)	−0.0048 (7)	0.0035 (7)	0.0007 (7)
C4'	0.0296 (9)	0.0197 (8)	0.0234 (8)	−0.0037 (7)	0.0037 (8)	−0.0005 (7)
C5'	0.0448 (10)	0.0219 (8)	0.0249 (8)	0.0016 (8)	−0.0034 (8)	0.0008 (7)
C6'	0.0377 (10)	0.0248 (8)	0.0253 (8)	−0.0002 (8)	0.0012 (8)	−0.0029 (7)
O6'	0.0363 (7)	0.0302 (7)	0.0329 (7)	−0.0019 (6)	0.0050 (6)	0.0053 (6)
C7'	0.0297 (9)	0.0324 (9)	0.0360 (10)	0.0018 (8)	−0.0011 (9)	−0.0013 (8)

Geometric parameters (Å, º) top

N1—C2	1.340 (2)	O1'—C2'	1.435 (2)
N1—C6	1.354 (2)	C2'—C3'	1.515 (2)
C2—N3	1.336 (2)	C2'—C6'	1.521 (2)
C2—H2	0.9300	C2'—H2'	0.9800
N3—C4	1.349 (2)	C3'—C7'	1.316 (2)
C4—N9	1.375 (2)	C3'—C4'	1.521 (2)
C4—C5	1.383 (2)	C4'—C5'	1.532 (2)
C5—N7	1.387 (2)	C4'—H4'	0.9800
C5—C6	1.410 (2)	C5'—H5'B	0.9700
C6—N6	1.336 (2)	C5'—H5'A	0.9700
N6—H6B	0.8600	C6'—O6'	1.420 (2)
N6—H6A	0.8600	C6'—H6'B	0.9700
N7—C8	1.314 (2)	C6'—H6'A	0.9700
C8—N9	1.370 (2)	O6'—H6'	0.8200
C8—H8	0.9300	C7'—H7'B	0.9300
N9—C4'	1.473 (2)	C7'—H7'A	0.9300
O1'—C5'	1.430 (2)

C2—N1—C6	118.34 (14)	O1'—C2'—H2'	109.3
N3—C2—N1	129.29 (16)	C3'—C2'—H2'	109.3
N3—C2—H2	115.4	C6'—C2'—H2'	109.3
N1—C2—H2	115.4	C7'—C3'—C2'	126.86 (17)
C2—N3—C4	110.58 (14)	C7'—C3'—C4'	126.04 (17)
N3—C4—N9	127.52 (15)	C2'—C3'—C4'	106.99 (13)
N3—C4—C5	126.90 (15)	N9—C4'—C3'	110.65 (13)
N9—C4—C5	105.54 (14)	N9—C4'—C5'	112.93 (14)
C4—C5—N7	110.88 (14)	C3'—C4'—C5'	102.22 (13)
C4—C5—C6	116.73 (15)	N9—C4'—H4'	110.3
N7—C5—C6	132.31 (15)	C3'—C4'—H4'	110.3
N6—C6—N1	118.50 (15)	C5'—C4'—H4'	110.3
N6—C6—C5	123.47 (16)	O1'—C5'—C4'	105.15 (13)
N1—C6—C5	118.02 (15)	O1'—C5'—H5'B	110.7
C6—N6—H6B	120.0	C4'—C5'—H5'B	110.7
C6—N6—H6A	120.0	O1'—C5'—H5'A	110.7
H6B—N6—H6A	120.0	C4'—C5'—H5'A	110.7
C8—N7—C5	103.83 (14)	H5'B—C5'—H5'A	108.8
N7—C8—N9	113.59 (15)	O6'—C6'—C2'	113.27 (14)
N7—C8—H8	123.2	O6'—C6'—H6'B	108.9
N9—C8—H8	123.2	C2'—C6'—H6'B	108.9
C8—N9—C4	106.16 (14)	O6'—C6'—H6'A	108.9
C8—N9—C4'	126.52 (14)	C2'—C6'—H6'A	108.9
C4—N9—C4'	127.26 (14)	H6'B—C6'—H6'A	107.7
C5'—O1'—C2'	106.28 (13)	C6'—O6'—H6'	109.5
O1'—C2'—C3'	104.11 (13)	C3'—C7'—H7'B	120.0
O1'—C2'—C6'	109.48 (14)	C3'—C7'—H7'A	120.0
C3'—C2'—C6'	115.18 (15)	H7'B—C7'—H7'A	120.0

C6—N1—C2—N3	0.8 (3)	N3—C4—N9—C4'	4.6 (3)
N1—C2—N3—C4	−3.1 (3)	C5—C4—N9—C4'	−177.47 (15)
C2—N3—C4—N9	179.76 (16)	C5'—O1'—C2'—C3'	36.01 (16)
C2—N3—C4—C5	2.3 (2)	C5'—O1'—C2'—C6'	159.67 (14)
N3—C4—C5—N7	177.82 (15)	O1'—C2'—C3'—C7'	158.59 (16)
N9—C4—C5—N7	−0.11 (18)	C6'—C2'—C3'—C7'	38.7 (2)
N3—C4—C5—C6	0.6 (2)	O1'—C2'—C3'—C4'	−17.90 (16)
N9—C4—C5—C6	−177.34 (14)	C6'—C2'—C3'—C4'	−137.78 (16)
C2—N1—C6—N6	−176.57 (15)	C8—N9—C4'—C3'	−46.5 (2)
C2—N1—C6—C5	2.5 (2)	C4—N9—C4'—C3'	130.41 (16)
C4—C5—C6—N6	175.94 (15)	C8—N9—C4'—C5'	67.3 (2)
N7—C5—C6—N6	−0.6 (3)	C4—N9—C4'—C5'	−115.70 (18)
C4—C5—C6—N1	−3.1 (2)	C7'—C3'—C4'—N9	−61.3 (2)
N7—C5—C6—N1	−179.57 (16)	C2'—C3'—C4'—N9	115.24 (15)
C4—C5—N7—C8	0.20 (18)	C7'—C3'—C4'—C5'	178.21 (17)
C6—C5—N7—C8	176.85 (18)	C2'—C3'—C4'—C5'	−5.26 (16)
C5—N7—C8—N9	−0.22 (18)	C2'—O1'—C5'—C4'	−40.20 (17)
N7—C8—N9—C4	0.16 (19)	N9—C4'—C5'—O1'	−91.97 (17)
N7—C8—N9—C4'	177.64 (15)	C3'—C4'—C5'—O1'	26.93 (17)
N3—C4—N9—C8	−177.94 (16)	O1'—C2'—C6'—O6'	−64.77 (19)
C5—C4—N9—C8	−0.02 (17)	C3'—C2'—C6'—O6'	52.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N1ⁱ	0.86	2.17	2.979 (2)	156
N6—H6B···N7ⁱⁱ	0.86	2.13	2.975 (2)	168
O6′—H6′···N3ⁱⁱⁱ	0.82	2.18	2.957 (2)	158
C8—H8···O6′	0.93	2.61	3.444 (2)	150

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

(II) top

Crystal data top

C₁₁H₁₃N₅O₂	F(000) = 520
M_r = 247.26	D_x = 1.444 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.496 (4) Å	Cell parameters from 22 reflections
b = 18.530 (6) Å	θ = 10.0–13.6°
c = 7.226 (2) Å	µ = 0.11 mm⁻¹
β = 90.81 (4)°	T = 200 K
V = 1137.5 (7) Å³	Prism, colourless
Z = 4	0.31 × 0.25 × 0.24 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.069
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.0°
Graphite monochromator	h = −10→10
θ–2θ scans	k = −21→21
5428 measured reflections	l = −6→8
2031 independent reflections	4 standard reflections every 120 min
1665 reflections with I > 2σ(I)	intensity decay: <2%

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0794P)² + 0.9198P] where P = (F_o² + 2F_c²)/3
2031 reflections	(Δ/σ)_max = 0.015
327 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₁H₁₃N₅O₂	V = 1137.5 (7) Å³
M_r = 247.26	Z = 4
Monoclinic, P2₁	Mo Kα radiation
a = 8.496 (4) Å	µ = 0.11 mm⁻¹
b = 18.530 (6) Å	T = 200 K
c = 7.226 (2) Å	0.31 × 0.25 × 0.24 mm
β = 90.81 (4)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.069
5428 measured reflections	4 standard reflections every 120 min
2031 independent reflections	intensity decay: <2%
1665 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	1 restraint
wR(F²) = 0.133	H-atom parameters constrained
S = 0.97	Δρ_max = 0.27 e Å⁻³
2031 reflections	Δρ_min = −0.29 e Å⁻³
327 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1A	0.0989 (5)	0.2273 (2)	0.4457 (6)	0.0258 (10)
C2A	0.0726 (6)	0.2636 (3)	0.5991 (7)	0.0252 (12)
H2A	−0.0315	0.2759	0.6213	0.030*
N3A	0.1785 (5)	0.2845 (2)	0.7261 (6)	0.0247 (10)
C4A	0.3318 (6)	0.2643 (3)	0.6939 (7)	0.0200 (11)
C5A	0.3694 (6)	0.2257 (3)	0.5378 (7)	0.0251 (12)
C6A	0.2499 (6)	0.2052 (3)	0.4085 (7)	0.0231 (11)
N6A	0.2740 (5)	0.1688 (3)	0.2562 (6)	0.0302 (11)
H6A1	0.1964	0.1592	0.1824	0.036*
H6A2	0.3673	0.1544	0.2300	0.036*
N7A	0.5308 (5)	0.2131 (3)	0.5411 (6)	0.0266 (10)
C8A	0.5762 (6)	0.2462 (3)	0.6985 (8)	0.0289 (12)
H8A	0.6810	0.2470	0.7375	0.035*
N9A	0.4603 (5)	0.2787 (2)	0.7984 (6)	0.0271 (10)
O1'A	−0.1319 (4)	0.34989 (19)	0.9012 (5)	0.0296 (9)
C2'A	−0.0613 (6)	0.4210 (3)	0.8949 (8)	0.0258 (12)
H2'A	−0.0649	0.4425	1.0186	0.031*
C3'A	0.1078 (6)	0.4056 (3)	0.8482 (7)	0.0248 (11)
C4'A	0.1406 (6)	0.3271 (3)	0.8943 (7)	0.0220 (11)
H4'A	0.2269	0.3236	0.9853	0.026*
C5'A	−0.0150 (7)	0.3042 (3)	0.9824 (9)	0.0332 (13)
H5'1	−0.0377	0.2539	0.9557	0.040*
H5'2	−0.0103	0.3107	1.1156	0.040*
C6'A	−0.1535 (7)	0.4666 (4)	0.7644 (9)	0.0395 (15)
H6'1	−0.0907	0.5081	0.7309	0.047*
H6'2	−0.1750	0.4392	0.6524	0.047*
O6'A	−0.2981 (5)	0.4909 (2)	0.8375 (7)	0.0475 (12)
H6'A	−0.3457	0.4566	0.8816	0.071*
C7'A	0.2108 (7)	0.4513 (3)	0.7794 (8)	0.0355 (14)
H7'1	0.1812	0.4987	0.7547	0.043*
H7'2	0.3128	0.4362	0.7555	0.043*
N1B	0.4063 (5)	0.6152 (2)	−0.0969 (6)	0.0232 (10)
C2B	0.4414 (6)	0.5805 (3)	0.0567 (7)	0.0260 (12)
H2B	0.5456	0.5662	0.0729	0.031*
N3B	0.3411 (5)	0.5634 (2)	0.1934 (6)	0.0224 (9)
C4B	0.1859 (6)	0.5823 (3)	0.1631 (7)	0.0231 (11)
C5B	0.1393 (6)	0.6163 (3)	−0.0006 (7)	0.0219 (11)
N6B	0.2215 (5)	0.6686 (3)	−0.2885 (6)	0.0278 (11)
H6B1	0.2958	0.6769	−0.3652	0.033*
H6B2	0.1268	0.6819	−0.3146	0.033*
C6B	0.2525 (6)	0.6355 (3)	−0.1323 (7)	0.0245 (11)
N7B	−0.0220 (5)	0.6259 (2)	0.0036 (6)	0.0266 (10)
C8B	−0.0562 (6)	0.5960 (3)	0.1669 (8)	0.0301 (13)
H8B	−0.1595	0.5943	0.2076	0.036*
N9B	0.0628 (5)	0.5683 (3)	0.2716 (6)	0.0293 (11)
O1'B	0.6395 (4)	0.4786 (2)	0.3358 (5)	0.0305 (9)
C2'B	0.5401 (6)	0.4157 (3)	0.3560 (8)	0.0295 (13)
H2'B	0.5603	0.3933	0.4769	0.035*
C3'B	0.3743 (6)	0.4454 (3)	0.3489 (7)	0.0232 (11)
C4'B	0.3857 (6)	0.5270 (3)	0.3681 (7)	0.0265 (12)
H4'B	0.3172	0.5434	0.4676	0.032*
C5'B	0.5577 (6)	0.5363 (3)	0.4267 (8)	0.0293 (12)
H5'3	0.5975	0.5828	0.3874	0.035*
H5'4	0.5698	0.5325	0.5601	0.035*
O6'B	0.5338 (4)	0.3902 (2)	0.0311 (5)	0.0322 (9)
H6'B	0.5062	0.3566	−0.0359	0.048*
C6'B	0.5784 (7)	0.3634 (3)	0.2055 (8)	0.0324 (13)
H6'3	0.6907	0.3538	0.2075	0.039*
H6'4	0.5242	0.3182	0.2277	0.039*
C7'B	0.2417 (7)	0.4077 (3)	0.3349 (8)	0.0346 (13)
H7'3	0.2453	0.3576	0.3283	0.042*
H7'4	0.1452	0.4314	0.3316	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.020 (2)	0.015 (2)	0.042 (3)	−0.0003 (18)	0.0022 (19)	−0.002 (2)
C2A	0.022 (3)	0.018 (3)	0.036 (3)	0.001 (2)	0.001 (2)	−0.002 (2)
N3A	0.020 (2)	0.015 (2)	0.039 (3)	0.0030 (17)	0.0052 (19)	−0.003 (2)
C4A	0.022 (2)	0.012 (2)	0.026 (3)	0.002 (2)	0.002 (2)	0.003 (2)
C5A	0.026 (3)	0.018 (3)	0.031 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
C6A	0.025 (3)	0.010 (2)	0.034 (3)	−0.001 (2)	0.002 (2)	0.001 (2)
N6A	0.022 (2)	0.030 (3)	0.038 (3)	0.001 (2)	0.000 (2)	−0.011 (2)
N7A	0.016 (2)	0.028 (3)	0.036 (2)	0.0011 (19)	0.0051 (18)	0.000 (2)
C8A	0.024 (3)	0.025 (3)	0.038 (3)	0.000 (2)	−0.001 (2)	−0.006 (3)
N9A	0.023 (2)	0.024 (2)	0.035 (2)	0.0000 (19)	0.0008 (19)	−0.009 (2)
O1'A	0.0224 (18)	0.0176 (19)	0.049 (2)	0.0016 (16)	0.0079 (16)	−0.0008 (18)
C2'A	0.029 (3)	0.012 (3)	0.036 (3)	0.003 (2)	0.004 (2)	−0.001 (2)
C3'A	0.029 (3)	0.013 (3)	0.033 (3)	0.003 (2)	0.003 (2)	−0.004 (2)
C4'A	0.020 (3)	0.015 (3)	0.031 (3)	0.002 (2)	0.006 (2)	−0.004 (2)
C5'A	0.033 (3)	0.022 (3)	0.045 (3)	0.007 (2)	0.011 (3)	−0.003 (3)
C6'A	0.032 (3)	0.036 (4)	0.050 (4)	0.011 (3)	0.006 (3)	0.003 (3)
O6'A	0.035 (2)	0.036 (3)	0.072 (3)	0.016 (2)	0.015 (2)	0.022 (3)
C7'A	0.045 (3)	0.014 (3)	0.048 (4)	−0.005 (2)	0.017 (3)	−0.004 (3)
N1B	0.017 (2)	0.017 (2)	0.035 (2)	−0.0011 (18)	0.0011 (18)	0.007 (2)
C2B	0.016 (2)	0.024 (3)	0.039 (3)	0.000 (2)	0.004 (2)	−0.001 (3)
N3B	0.020 (2)	0.017 (2)	0.031 (2)	0.0054 (18)	0.0039 (17)	0.003 (2)
C4B	0.020 (2)	0.020 (3)	0.029 (3)	−0.005 (2)	0.002 (2)	0.000 (2)
C5B	0.020 (3)	0.013 (2)	0.033 (3)	−0.002 (2)	0.001 (2)	−0.003 (2)
N6B	0.016 (2)	0.031 (3)	0.037 (3)	0.0018 (19)	0.0047 (19)	0.011 (2)
C6B	0.024 (3)	0.016 (3)	0.034 (3)	−0.006 (2)	0.005 (2)	−0.003 (2)
N7B	0.020 (2)	0.019 (2)	0.041 (3)	0.0007 (18)	0.0016 (19)	0.004 (2)
C8B	0.017 (2)	0.030 (3)	0.043 (3)	−0.001 (2)	0.008 (2)	−0.001 (3)
N9B	0.022 (2)	0.023 (2)	0.044 (3)	0.004 (2)	0.008 (2)	0.005 (2)
O1'B	0.0248 (19)	0.0212 (19)	0.046 (2)	0.0030 (16)	0.0038 (16)	−0.0025 (18)
C2'B	0.031 (3)	0.016 (3)	0.041 (3)	0.006 (2)	−0.004 (2)	0.010 (3)
C3'B	0.026 (3)	0.016 (2)	0.027 (3)	0.001 (2)	0.005 (2)	0.001 (2)
C4'B	0.028 (3)	0.023 (3)	0.028 (3)	0.007 (2)	0.001 (2)	−0.001 (2)
C5'B	0.030 (3)	0.020 (3)	0.038 (3)	0.004 (2)	−0.002 (2)	−0.002 (2)
O6'B	0.032 (2)	0.024 (2)	0.041 (2)	−0.0012 (17)	0.0007 (17)	−0.0058 (18)
C6'B	0.032 (3)	0.019 (3)	0.046 (3)	0.004 (2)	0.003 (3)	−0.002 (3)
C7'B	0.028 (3)	0.030 (3)	0.046 (3)	−0.003 (2)	0.000 (3)	0.005 (3)

Geometric parameters (Å, º) top

N1A—C2A	1.318 (7)	N1B—C2B	1.314 (7)
N1A—C6A	1.377 (7)	N1B—C6B	1.380 (6)
C2A—N3A	1.333 (7)	C2B—N3B	1.351 (7)
C2A—H2A	0.9300	C2B—H2B	0.9300
N3A—C4A	1.379 (6)	N3B—C4B	1.379 (6)
N3A—C4'A	1.489 (6)	N3B—C4'B	1.476 (7)
C4A—N9A	1.345 (7)	C4B—N9B	1.341 (7)
C4A—C5A	1.377 (7)	C4B—C5B	1.392 (8)
C5A—N7A	1.391 (7)	C5B—N7B	1.383 (7)
C5A—C6A	1.421 (7)	C5B—C6B	1.408 (7)
C6A—N6A	1.310 (7)	N6B—C6B	1.308 (7)
N6A—H6A1	0.8600	N6B—H6B1	0.8600
N6A—H6A2	0.8600	N6B—H6B2	0.8600
N7A—C8A	1.343 (7)	N7B—C8B	1.339 (7)
C8A—N9A	1.369 (7)	C8B—N9B	1.355 (7)
C8A—H8A	0.9300	C8B—H8B	0.9300
O1'A—C5'A	1.425 (7)	O1'B—C5'B	1.440 (7)
O1'A—C2'A	1.448 (6)	O1'B—C2'B	1.447 (7)
C2'A—C6'A	1.482 (8)	C2'B—C6'B	1.497 (8)
C2'A—C3'A	1.507 (7)	C2'B—C3'B	1.512 (8)
C2'A—H2'A	0.9800	C2'B—H2'B	0.9800
C3'A—C7'A	1.321 (8)	C3'B—C7'B	1.328 (8)
C3'A—C4'A	1.516 (7)	C3'B—C4'B	1.522 (8)
C4'A—C5'A	1.535 (8)	C4'B—C5'B	1.526 (7)
C4'A—H4'A	0.9800	C4'B—H4'B	0.9800
C5'A—H5'1	0.9700	C5'B—H5'3	0.9700
C5'A—H5'2	0.9700	C5'B—H5'4	0.9700
C6'A—O6'A	1.417 (7)	O6'B—C6'B	1.402 (7)
C6'A—H6'1	0.9700	O6'B—H6'B	0.8200
C6'A—H6'2	0.9700	C6'B—H6'3	0.9700
O6'A—H6'A	0.8200	C6'B—H6'4	0.9700
C7'A—H7'1	0.9300	C7'B—H7'3	0.9300
C7'A—H7'2	0.9300	C7'B—H7'4	0.9300

C2A—N1A—C6A	119.0 (4)	C2B—N1B—C6B	119.6 (4)
N1A—C2A—N3A	127.3 (5)	N1B—C2B—N3B	126.5 (5)
N1A—C2A—H2A	116.3	N1B—C2B—H2B	116.8
N3A—C2A—H2A	116.3	N3B—C2B—H2B	116.8
C2A—N3A—C4A	115.8 (4)	C2B—N3B—C4B	115.9 (4)
C2A—N3A—C4'A	124.4 (4)	C2B—N3B—C4'B	125.1 (4)
C4A—N3A—C4'A	119.8 (4)	C4B—N3B—C4'B	119.0 (4)
N9A—C4A—N3A	127.8 (4)	N9B—C4B—N3B	127.6 (5)
N9A—C4A—C5A	111.5 (4)	N9B—C4B—C5B	111.6 (4)
N3A—C4A—C5A	120.6 (4)	N3B—C4B—C5B	120.6 (4)
C4A—C5A—N7A	108.2 (4)	N7B—C5B—C4B	108.0 (4)
C4A—C5A—C6A	120.4 (5)	N7B—C5B—C6B	131.9 (5)
N7A—C5A—C6A	131.4 (5)	C4B—C5B—C6B	120.0 (5)
N6A—C6A—N1A	118.3 (5)	C6B—N6B—H6B1	120.0
N6A—C6A—C5A	124.8 (5)	C6B—N6B—H6B2	120.0
N1A—C6A—C5A	116.8 (5)	H6B1—N6B—H6B2	120.0
C6A—N6A—H6A1	120.0	N6B—C6B—N1B	117.8 (4)
C6A—N6A—H6A2	120.0	N6B—C6B—C5B	124.8 (5)
H6A1—N6A—H6A2	120.0	N1B—C6B—C5B	117.3 (5)
C8A—N7A—C5A	102.1 (4)	C8B—N7B—C5B	101.2 (4)
N7A—C8A—N9A	116.6 (5)	N7B—C8B—N9B	118.6 (5)
N7A—C8A—H8A	121.7	N7B—C8B—H8B	120.7
N9A—C8A—H8A	121.7	N9B—C8B—H8B	120.7
C4A—N9A—C8A	101.6 (4)	C4B—N9B—C8B	100.5 (4)
C5'A—O1'A—C2'A	105.5 (4)	C5'B—O1'B—C2'B	105.4 (4)
O1'A—C2'A—C6'A	108.8 (4)	O1'B—C2'B—C6'B	108.3 (5)
O1'A—C2'A—C3'A	103.4 (4)	O1'B—C2'B—C3'B	104.4 (4)
C6'A—C2'A—C3'A	117.6 (5)	C6'B—C2'B—C3'B	115.0 (5)
O1'A—C2'A—H2'A	108.9	O1'B—C2'B—H2'B	109.6
C6'A—C2'A—H2'A	108.9	C6'B—C2'B—H2'B	109.6
C3'A—C2'A—H2'A	108.9	C3'B—C2'B—H2'B	109.6
C7'A—C3'A—C2'A	127.0 (5)	C7'B—C3'B—C2'B	126.9 (5)
C7'A—C3'A—C4'A	125.3 (5)	C7'B—C3'B—C4'B	125.6 (5)
C2'A—C3'A—C4'A	107.8 (4)	C2'B—C3'B—C4'B	107.4 (4)
N3A—C4'A—C3'A	111.7 (4)	N3B—C4'B—C3'B	111.2 (4)
N3A—C4'A—C5'A	112.9 (4)	N3B—C4'B—C5'B	114.8 (4)
C3'A—C4'A—C5'A	101.5 (4)	C3'B—C4'B—C5'B	101.4 (4)
N3A—C4'A—H4'A	110.1	N3B—C4'B—H4'B	109.7
C3'A—C4'A—H4'A	110.1	C3'B—C4'B—H4'B	109.7
C5'A—C4'A—H4'A	110.1	C5'B—C4'B—H4'B	109.7
O1'A—C5'A—C4'A	105.3 (4)	O1'B—C5'B—C4'B	104.8 (4)
O1'A—C5'A—H5'1	110.7	O1'B—C5'B—H5'3	110.8
C4'A—C5'A—H5'1	110.7	C4'B—C5'B—H5'3	110.8
O1'A—C5'A—H5'2	110.7	O1'B—C5'B—H5'4	110.8
C4'A—C5'A—H5'2	110.7	C4'B—C5'B—H5'4	110.8
H5'1—C5'A—H5'2	108.8	H5'3—C5'B—H5'4	108.9
O6'A—C6'A—C2'A	113.4 (5)	C6'B—O6'B—H6'B	109.5
O6'A—C6'A—H6'1	108.9	O6'B—C6'B—C2'B	111.4 (4)
C2'A—C6'A—H6'1	108.9	O6'B—C6'B—H6'3	109.4
O6'A—C6'A—H6'2	108.9	C2'B—C6'B—H6'3	109.4
C2'A—C6'A—H6'2	108.9	O6'B—C6'B—H6'4	109.4
H6'1—C6'A—H6'2	107.7	C2'B—C6'B—H6'4	109.4
C6'A—O6'A—H6'A	109.5	H6'3—C6'B—H6'4	108.0
C3'A—C7'A—H7'1	120.0	C3'B—C7'B—H7'3	120.0
C3'A—C7'A—H7'2	120.0	C3'B—C7'B—H7'4	120.0
H7'1—C7'A—H7'2	120.0	H7'3—C7'B—H7'4	120.0

C6A—N1A—C2A—N3A	2.3 (8)	C6B—N1B—C2B—N3B	−2.4 (8)
N1A—C2A—N3A—C4A	−1.5 (8)	N1B—C2B—N3B—C4B	2.8 (8)
N1A—C2A—N3A—C4'A	178.3 (5)	N1B—C2B—N3B—C4'B	−177.2 (5)
C2A—N3A—C4A—N9A	179.5 (5)	C2B—N3B—C4B—N9B	176.3 (5)
C4'A—N3A—C4A—N9A	−0.3 (8)	C4'B—N3B—C4B—N9B	−3.6 (8)
C2A—N3A—C4A—C5A	0.8 (7)	C2B—N3B—C4B—C5B	0.4 (7)
C4'A—N3A—C4A—C5A	−179.1 (5)	C4'B—N3B—C4B—C5B	−179.6 (5)
N9A—C4A—C5A—N7A	1.0 (6)	N9B—C4B—C5B—N7B	1.0 (6)
N3A—C4A—C5A—N7A	179.9 (4)	N3B—C4B—C5B—N7B	177.6 (4)
N9A—C4A—C5A—C6A	−179.9 (5)	N9B—C4B—C5B—C6B	179.8 (5)
N3A—C4A—C5A—C6A	−0.9 (7)	N3B—C4B—C5B—C6B	−3.7 (7)
C2A—N1A—C6A—N6A	179.5 (5)	C2B—N1B—C6B—N6B	−178.4 (5)
C2A—N1A—C6A—C5A	−2.2 (7)	C2B—N1B—C6B—C5B	−1.1 (7)
C4A—C5A—C6A—N6A	179.8 (5)	N7B—C5B—C6B—N6B	−0.5 (9)
N7A—C5A—C6A—N6A	−1.2 (9)	C4B—C5B—C6B—N6B	−178.9 (5)
C4A—C5A—C6A—N1A	1.6 (7)	N7B—C5B—C6B—N1B	−177.6 (5)
N7A—C5A—C6A—N1A	−179.5 (5)	C4B—C5B—C6B—N1B	4.0 (7)
C4A—C5A—N7A—C8A	−0.8 (6)	C4B—C5B—N7B—C8B	−0.8 (5)
C6A—C5A—N7A—C8A	−179.8 (6)	C6B—C5B—N7B—C8B	−179.4 (6)
C5A—N7A—C8A—N9A	0.4 (6)	C5B—N7B—C8B—N9B	0.5 (6)
N3A—C4A—N9A—C8A	−179.5 (5)	N3B—C4B—N9B—C8B	−176.9 (5)
C5A—C4A—N9A—C8A	−0.7 (6)	C5B—C4B—N9B—C8B	−0.7 (6)
N7A—C8A—N9A—C4A	0.1 (6)	N7B—C8B—N9B—C4B	0.1 (7)
C5'A—O1'A—C2'A—C6'A	163.3 (4)	C5'B—O1'B—C2'B—C6'B	156.8 (4)
C5'A—O1'A—C2'A—C3'A	37.6 (5)	C5'B—O1'B—C2'B—C3'B	33.8 (5)
O1'A—C2'A—C3'A—C7'A	160.7 (5)	O1'B—C2'B—C3'B—C7'B	169.5 (5)
C6'A—C2'A—C3'A—C7'A	40.7 (8)	C6'B—C2'B—C3'B—C7'B	50.9 (8)
O1'A—C2'A—C3'A—C4'A	−19.3 (5)	O1'B—C2'B—C3'B—C4'B	−12.6 (6)
C6'A—C2'A—C3'A—C4'A	−139.2 (5)	C6'B—C2'B—C3'B—C4'B	−131.2 (5)
C2A—N3A—C4'A—C3'A	−74.7 (6)	C2B—N3B—C4'B—C3'B	−89.8 (6)
C4A—N3A—C4'A—C3'A	105.1 (5)	C4B—N3B—C4'B—C3'B	90.1 (5)
C2A—N3A—C4'A—C5'A	39.0 (7)	C2B—N3B—C4'B—C5'B	24.5 (7)
C4A—N3A—C4'A—C5'A	−141.2 (5)	C4B—N3B—C4'B—C5'B	−155.5 (5)
C7'A—C3'A—C4'A—N3A	−64.0 (7)	C7'B—C3'B—C4'B—N3B	−71.3 (7)
C2'A—C3'A—C4'A—N3A	116.0 (5)	C2'B—C3'B—C4'B—N3B	110.7 (5)
C7'A—C3'A—C4'A—C5'A	175.5 (5)	C7'B—C3'B—C4'B—C5'B	166.2 (6)
C2'A—C3'A—C4'A—C5'A	−4.6 (5)	C2'B—C3'B—C4'B—C5'B	−11.8 (6)
C2'A—O1'A—C5'A—C4'A	−41.6 (5)	C2'B—O1'B—C5'B—C4'B	−42.3 (5)
N3A—C4'A—C5'A—O1'A	−92.2 (5)	N3B—C4'B—C5'B—O1'B	−87.5 (5)
C3'A—C4'A—C5'A—O1'A	27.6 (5)	C3'B—C4'B—C5'B—O1'B	32.4 (5)
O1'A—C2'A—C6'A—O6'A	75.8 (6)	O1'B—C2'B—C6'B—O6'B	−67.4 (6)
C3'A—C2'A—C6'A—O6'A	−167.2 (5)	C3'B—C2'B—C6'B—O6'B	49.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6A—H6A1···N7Bⁱ	0.86	2.08	2.937 (6)	174
N6A—H6A2···N1Bⁱⁱ	0.86	2.28	3.127 (6)	168
O6′A—H6′A···O6′Bⁱⁱⁱ	0.82	1.94	2.745 (6)	167
N6B—H6B1···N7A^iv	0.86	2.07	2.924 (6)	172
N6B—H8B2···N1A^v	0.86	2.29	3.130 (6)	167
O6′B—H6′B···N9A^vi	0.82	1.91	2.731 (5)	175

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

Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₁₁H₁₃N₅O₂	C₁₁H₁₃N₅O₂
M_r	247.26	247.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Monoclinic, P2₁
Temperature (K)	210	200
a, b, c (Å)	9.727 (2), 16.632 (4), 7.104 (2)	8.496 (4), 18.530 (6), 7.226 (2)
α, β, γ (°)	90, 90, 90	90, 90.81 (4), 90
V (Å³)	1149.3 (5)	1137.5 (7)
Z	4	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.10	0.11
Crystal size (mm)	0.36 × 0.24 × 0.21	0.31 × 0.25 × 0.24

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4469, 1193, 1133	5428, 2031, 1665
R_int	0.024	0.069
(sin θ/λ)_max (Å⁻¹)	0.595	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.064, 1.11	0.049, 0.133, 0.97
No. of reflections	1193	2031
No. of parameters	166	327
No. of restraints	0	1
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.10	0.27, −0.29

Computer programs: CAD-4 Operations Manual (Enraf-Nonius,1977), CAD-4 Operations Manual, MolEN (Fair,1990), SHELXTL (Sheldrick, 1995), SHELXL97 (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) for (I) top

N1—C2	1.340 (2)	C8—N9	1.370 (2)
N1—C6	1.354 (2)	N9—C4'	1.473 (2)
C2—N3	1.336 (2)	O1'—C5'	1.430 (2)
N3—C4	1.349 (2)	O1'—C2'	1.435 (2)
C4—N9	1.375 (2)	C2'—C3'	1.515 (2)
C4—C5	1.383 (2)	C2'—C6'	1.521 (2)
C5—N7	1.387 (2)	C3'—C7'	1.316 (2)
C5—C6	1.410 (2)	C3'—C4'	1.521 (2)
C6—N6	1.336 (2)	C4'—C5'	1.532 (2)
N7—C8	1.314 (2)	C6'—O6'	1.420 (2)

C2—N1—C6	118.34 (14)	C8—N9—C4'	126.52 (14)
N3—C2—N1	129.29 (16)	C4—N9—C4'	127.26 (14)
C2—N3—C4	110.58 (14)	C5'—O1'—C2'	106.28 (13)
N3—C4—N9	127.52 (15)	O1'—C2'—C3'	104.11 (13)
N3—C4—C5	126.90 (15)	O1'—C2'—C6'	109.48 (14)
N9—C4—C5	105.54 (14)	C3'—C2'—C6'	115.18 (15)
C4—C5—N7	110.88 (14)	C7'—C3'—C2'	126.86 (17)
C4—C5—C6	116.73 (15)	C7'—C3'—C4'	126.04 (17)
N7—C5—C6	132.31 (15)	C2'—C3'—C4'	106.99 (13)
N6—C6—N1	118.50 (15)	N9—C4'—C3'	110.65 (13)
N6—C6—C5	123.47 (16)	N9—C4'—C5'	112.93 (14)
N1—C6—C5	118.02 (15)	C3'—C4'—C5'	102.22 (13)
C8—N7—C5	103.83 (14)	O1'—C5'—C4'	105.15 (13)
N7—C8—N9	113.59 (15)	O6'—C6'—C2'	113.27 (14)
C8—N9—C4	106.16 (14)

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6A···N1ⁱ	0.86	2.17	2.979 (2)	156
N6—H6B···N7ⁱⁱ	0.86	2.13	2.975 (2)	168
O6'—H6'···N3ⁱⁱⁱ	0.82	2.18	2.957 (2)	158
C8—H8···O6'	0.93	2.61	3.444 (2)	150

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

Selected geometric parameters (Å, º) for (II) top

N1A—C2A	1.318 (7)	N1B—C2B	1.314 (7)
N1A—C6A	1.377 (7)	N1B—C6B	1.380 (6)
C2A—N3A	1.333 (7)	C2B—N3B	1.351 (7)
N3A—C4A	1.379 (6)	N3B—C4B	1.379 (6)
N3A—C4'A	1.489 (6)	N3B—C4'B	1.476 (7)
C4A—N9A	1.345 (7)	C4B—N9B	1.341 (7)
C4A—C5A	1.377 (7)	C4B—C5B	1.392 (8)
C5A—N7A	1.391 (7)	C5B—N7B	1.383 (7)
C5A—C6A	1.421 (7)	C5B—C6B	1.408 (7)
C6A—N6A	1.310 (7)	N6B—C6B	1.308 (7)
N7A—C8A	1.343 (7)	N7B—C8B	1.339 (7)
C8A—N9A	1.369 (7)	C8B—N9B	1.355 (7)
O1'A—C5'A	1.425 (7)	O1'B—C5'B	1.440 (7)
O1'A—C2'A	1.448 (6)	O1'B—C2'B	1.447 (7)
C2'A—C6'A	1.482 (8)	C2'B—C6'B	1.497 (8)
C2'A—C3'A	1.507 (7)	C2'B—C3'B	1.512 (8)
C3'A—C7'A	1.321 (8)	C3'B—C7'B	1.328 (8)
C3'A—C4'A	1.516 (7)	C3'B—C4'B	1.522 (8)
C4'A—C5'A	1.535 (8)	C4'B—C5'B	1.526 (7)
C6'A—O6'A	1.417 (7)	O6'B—C6'B	1.402 (7)

C2A—N1A—C6A	119.0 (4)	C2B—N1B—C6B	119.6 (4)
N1A—C2A—N3A	127.3 (5)	N1B—C2B—N3B	126.5 (5)
C2A—N3A—C4A	115.8 (4)	C2B—N3B—C4B	115.9 (4)
C2A—N3A—C4'A	124.4 (4)	C2B—N3B—C4'B	125.1 (4)
C4A—N3A—C4'A	119.8 (4)	C4B—N3B—C4'B	119.0 (4)
N9A—C4A—N3A	127.8 (4)	N9B—C4B—N3B	127.6 (5)
N9A—C4A—C5A	111.5 (4)	N9B—C4B—C5B	111.6 (4)
N3A—C4A—C5A	120.6 (4)	N3B—C4B—C5B	120.6 (4)
C4A—C5A—N7A	108.2 (4)	N7B—C5B—C4B	108.0 (4)
C4A—C5A—C6A	120.4 (5)	N7B—C5B—C6B	131.9 (5)
N7A—C5A—C6A	131.4 (5)	C4B—C5B—C6B	120.0 (5)
N6A—C6A—N1A	118.3 (5)	N6B—C6B—N1B	117.8 (4)
N6A—C6A—C5A	124.8 (5)	N6B—C6B—C5B	124.8 (5)
N1A—C6A—C5A	116.8 (5)	N1B—C6B—C5B	117.3 (5)
C8A—N7A—C5A	102.1 (4)	C8B—N7B—C5B	101.2 (4)
N7A—C8A—N9A	116.6 (5)	N7B—C8B—N9B	118.6 (5)
C4A—N9A—C8A	101.6 (4)	C4B—N9B—C8B	100.5 (4)
C5'A—O1'A—C2'A	105.5 (4)	C5'B—O1'B—C2'B	105.4 (4)
O1'A—C2'A—C6'A	108.8 (4)	O1'B—C2'B—C6'B	108.3 (5)
O1'A—C2'A—C3'A	103.4 (4)	O1'B—C2'B—C3'B	104.4 (4)
C6'A—C2'A—C3'A	117.6 (5)	C6'B—C2'B—C3'B	115.0 (5)
C7'A—C3'A—C2'A	127.0 (5)	C7'B—C3'B—C2'B	126.9 (5)
C7'A—C3'A—C4'A	125.3 (5)	C7'B—C3'B—C4'B	125.6 (5)
C2'A—C3'A—C4'A	107.8 (4)	C2'B—C3'B—C4'B	107.4 (4)
N3A—C4'A—C3'A	111.7 (4)	N3B—C4'B—C3'B	111.2 (4)
N3A—C4'A—C5'A	112.9 (4)	N3B—C4'B—C5'B	114.8 (4)
C3'A—C4'A—C5'A	101.5 (4)	C3'B—C4'B—C5'B	101.4 (4)
O1'A—C5'A—C4'A	105.3 (4)	O1'B—C5'B—C4'B	104.8 (4)
O6'A—C6'A—C2'A	113.4 (5)	O6'B—C6'B—C2'B	111.4 (4)

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
N6A—H6A1···N7Bⁱ	0.86	2.08	2.937 (6)	174
N6A—H6A2···N1Bⁱⁱ	0.86	2.28	3.127 (6)	168
O6'A—H6'A···O6'Bⁱⁱⁱ	0.82	1.94	2.745 (6)	167
N6B—H6B1···N7A^iv	0.86	2.07	2.924 (6)	172
N6B—H8B2···N1A^v	0.86	2.29	3.130 (6)	167
O6'B—H6'B···N9A^vi	0.82	1.91	2.731 (5)	175

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

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Two isomeric di­deoxy­nucleosides

Supporting information

Two isomeric dideoxynucleosides