α-Thymidine at 105 K

Görbitz, C.H.; Nelson, W.H.; Sagstuen, E.

doi:10.1107/S1600536805009700

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α-Thymidine at 105 K

C. H. Görbitz, W. H. Nelson and E. Sagstuen

Two independent molecules in the crystal structure of the title nucleoside, 1-(2-deoxy-α-D-ribofuranosyl)-5-methyluracil, C₁₀H₁₄N₂O₅, form a dimer connected by two inter-base hydrogen bonds. The ring puckering modes are envelope C4′-endo and half-chair C3′-exo-C4′-endo, respectively, which are quite uncommon conformations for 2′-deoxyriboses.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805009700/fl6154sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805009700/fl6154Isup2.hkl Contains datablock I

CCDC reference: 271873

checkCIF report

Key indicators

Single-crystal X-ray study
T = 105 K
Mean (C-C) = 0.001 Å
R factor = 0.032
wR factor = 0.086
Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size .......       0.85 mm

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.802     0.938
            Tmin' and Tmax expected:      0.904     0.938
            RR' =      0.887
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.07
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.25
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         20

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           40.53
           From the CIF: _reflns_number_total               6311
           Count of symmetry unique reflns         7184
           Completeness (_total/calc)             87.85%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-(2-Deoxy-α-D-ribofuranosyl)-5-methyluracil top

Crystal data top

C₁₀H₁₄N₂O₅	Z = 2
M_r = 242.23	F(000) = 256
Triclinic, P1	D_x = 1.438 Mg m⁻³
a = 5.838 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.883 (4) Å	Cell parameters from 7621 reflections
c = 10.576 (4) Å	θ = 2.1–40.5°
α = 107.225 (14)°	µ = 0.12 mm⁻¹
β = 100.203 (14)°	T = 105 K
γ = 98.894 (14)°	Block, colourless
V = 559.5 (4) Å³	0.85 × 0.75 × 0.55 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	6311 independent reflections
Radiation source: fine-focus sealed tube	6021 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
Detector resolution: 8.3 pixels mm^-1	θ_max = 40.5°, θ_min = 2.1°
Sets of exposures each taken over 0.3° ω rotation scans	h = −9→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→17
T_min = 0.802, T_max = 0.938	l = −19→19
10979 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0624P)² + 0.0016P] where P = (F_o² + 2F_c²)/3
6311 reflections	(Δ/σ)_max < 0.001
327 parameters	Δρ_max = 0.56 e Å⁻³
3 restraints	Δρ_min = −0.18 e Å⁻³

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. Data were collected by measuring two sets of exposures with the detector set at 2θ = 29° and three sets of exposures with the detector set at 2θ = 55°, crystal-to-detector distance 5.00 cm. Refinement of F² against ALL reflections.

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

	x	y	z	U_iso*/U_eq
O2A	0.99446 (13)	0.60401 (9)	0.20607 (7)	0.02154 (12)
O4A	0.53074 (15)	0.79306 (11)	−0.06091 (7)	0.02684 (16)
O3'A	0.38596 (13)	0.80434 (11)	0.55607 (8)	0.02685 (16)
H3'A	0.338 (5)	0.850 (3)	0.621 (3)	0.040*
O4'A	0.89252 (10)	0.84899 (6)	0.53619 (6)	0.01408 (9)
O5'A	1.21317 (12)	0.89927 (8)	0.78953 (7)	0.02065 (11)
H5'A	1.302 (4)	0.871 (2)	0.843 (2)	0.031*
N1A	0.73696 (12)	0.73467 (8)	0.30135 (7)	0.01455 (10)
N3A	0.75051 (13)	0.69610 (9)	0.07467 (7)	0.01668 (11)
H3A	0.805 (3)	0.646 (2)	0.0082 (19)	0.020*
C2A	0.83777 (14)	0.67390 (9)	0.19547 (7)	0.01493 (11)
C4A	0.58619 (14)	0.77987 (10)	0.05303 (8)	0.01652 (12)
C5A	0.49125 (14)	0.84449 (9)	0.16944 (7)	0.01536 (11)
C6A	0.56658 (13)	0.81612 (9)	0.28648 (7)	0.01512 (11)
H61A	0.4994	0.8538	0.3615	0.018*
C7A	0.31675 (18)	0.93993 (12)	0.15600 (10)	0.02313 (16)
H71A	0.2520	0.9637	0.2373	0.035*
H72A	0.1863	0.8885	0.0752	0.035*
H73A	0.3985	1.0296	0.1467	0.035*
C1'A	0.81025 (14)	0.70905 (8)	0.43197 (7)	0.01396 (11)
H11A	0.9434	0.6565	0.4281	0.017*
C2'A	0.60614 (16)	0.62447 (10)	0.47267 (8)	0.01959 (14)
H21A	0.4595	0.5897	0.3983	0.024*
H22A	0.6523	0.5400	0.4939	0.024*
C3'A	0.56696 (14)	0.73461 (10)	0.59950 (8)	0.01779 (13)
H31A	0.5245	0.6875	0.6664	0.021*
C4'A	0.81051 (13)	0.84212 (9)	0.65648 (7)	0.01402 (11)
H41A	0.7875	0.9399	0.7075	0.017*
C5'A	0.98963 (15)	0.79587 (10)	0.74950 (8)	0.01805 (13)
H51A	0.9311	0.7923	0.8310	0.022*
H52A	1.0104	0.6979	0.7009	0.022*
O2B	−0.07623 (14)	0.52463 (8)	0.85938 (7)	0.02202 (12)
O4B	0.46198 (14)	0.39902 (10)	1.14759 (7)	0.02398 (13)
O3'B	0.22204 (13)	0.06900 (8)	0.48502 (7)	0.01989 (11)
H3'B	0.148 (4)	0.000 (2)	0.503 (2)	0.030*
O4'B	0.18710 (15)	0.38733 (8)	0.55097 (7)	0.02310 (13)
O5'B	−0.23065 (16)	0.30407 (12)	0.31947 (10)	0.03125 (17)
H5'B	−0.292 (5)	0.324 (3)	0.264 (3)	0.047*
N1B	0.14988 (15)	0.36854 (9)	0.76382 (7)	0.01881 (12)
N3B	0.20318 (14)	0.46219 (9)	0.99941 (7)	0.01726 (11)
H3B	0.147 (3)	0.515 (2)	1.0612 (19)	0.021*
C2B	0.08264 (15)	0.45638 (9)	0.87243 (8)	0.01610 (12)
C4B	0.37674 (14)	0.38616 (9)	1.02740 (8)	0.01623 (12)
C5B	0.44383 (15)	0.29765 (9)	0.90897 (8)	0.01755 (12)
C6B	0.32851 (17)	0.29357 (10)	0.78413 (9)	0.01985 (14)
H61B	0.3721	0.2364	0.7064	0.024*
C7B	0.63390 (18)	0.21410 (12)	0.93006 (10)	0.02398 (16)
H71B	0.6656	0.1644	0.8421	0.036*
H72B	0.5793	0.1422	0.9714	0.036*
H73B	0.7804	0.2813	0.9905	0.036*
C1'B	0.01834 (16)	0.34594 (9)	0.62248 (8)	0.01850 (13)
H11B	−0.1010	0.4087	0.6256	0.022*
C2'B	−0.11032 (15)	0.18592 (9)	0.54249 (9)	0.01833 (13)
H21B	−0.1105	0.1273	0.6039	0.022*
H22B	−0.2772	0.1792	0.4970	0.022*
C3'B	0.03540 (15)	0.13386 (9)	0.43691 (8)	0.01636 (12)
H31B	−0.0711	0.0663	0.3487	0.020*
C4'B	0.15448 (15)	0.27520 (9)	0.42040 (8)	0.01661 (12)
H41B	0.3147	0.2661	0.4021	0.020*
C5'B	0.00923 (18)	0.31191 (11)	0.30524 (9)	0.02135 (14)
H51B	0.0801	0.4109	0.3084	0.026*
H52B	0.0114	0.2426	0.2163	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2A	0.0249 (3)	0.0316 (3)	0.0164 (2)	0.0168 (3)	0.0098 (2)	0.0118 (2)
O4A	0.0293 (3)	0.0467 (4)	0.0142 (2)	0.0207 (3)	0.0081 (2)	0.0163 (3)
O3'A	0.0170 (3)	0.0507 (5)	0.0211 (3)	0.0143 (3)	0.0076 (2)	0.0187 (3)
O4'A	0.0161 (2)	0.0163 (2)	0.01037 (19)	0.00158 (16)	0.00391 (15)	0.00579 (17)
O5'A	0.0162 (2)	0.0279 (3)	0.0176 (3)	0.0032 (2)	0.00028 (18)	0.0102 (2)
N1A	0.0158 (2)	0.0199 (3)	0.0106 (2)	0.0067 (2)	0.00457 (17)	0.0068 (2)
N3A	0.0188 (3)	0.0243 (3)	0.0107 (2)	0.0090 (2)	0.00591 (19)	0.0077 (2)
C2A	0.0161 (3)	0.0198 (3)	0.0114 (3)	0.0061 (2)	0.0052 (2)	0.0066 (2)
C4A	0.0159 (3)	0.0245 (3)	0.0118 (3)	0.0069 (2)	0.0045 (2)	0.0080 (2)
C5A	0.0144 (3)	0.0209 (3)	0.0122 (3)	0.0056 (2)	0.00331 (19)	0.0065 (2)
C6A	0.0149 (3)	0.0198 (3)	0.0116 (3)	0.0054 (2)	0.00392 (19)	0.0052 (2)
C7A	0.0232 (4)	0.0334 (4)	0.0191 (3)	0.0158 (3)	0.0068 (3)	0.0119 (3)
C1'A	0.0165 (3)	0.0162 (3)	0.0106 (2)	0.0042 (2)	0.00425 (19)	0.0055 (2)
C2'A	0.0225 (3)	0.0197 (3)	0.0146 (3)	−0.0019 (3)	0.0053 (2)	0.0056 (3)
C3'A	0.0142 (3)	0.0275 (3)	0.0143 (3)	0.0037 (2)	0.0052 (2)	0.0102 (3)
C4'A	0.0154 (3)	0.0183 (3)	0.0106 (2)	0.0056 (2)	0.00430 (19)	0.0065 (2)
C5'A	0.0179 (3)	0.0238 (3)	0.0144 (3)	0.0038 (2)	0.0021 (2)	0.0106 (3)
O2B	0.0280 (3)	0.0273 (3)	0.0167 (2)	0.0160 (3)	0.0077 (2)	0.0097 (2)
O4B	0.0249 (3)	0.0342 (3)	0.0134 (2)	0.0113 (3)	0.0015 (2)	0.0080 (2)
O3'B	0.0238 (3)	0.0188 (2)	0.0212 (3)	0.0084 (2)	0.0065 (2)	0.0101 (2)
O4'B	0.0349 (4)	0.0170 (2)	0.0140 (2)	−0.0024 (2)	0.0051 (2)	0.0046 (2)
O5'B	0.0259 (3)	0.0491 (5)	0.0319 (4)	0.0173 (3)	0.0084 (3)	0.0271 (4)
N1B	0.0250 (3)	0.0218 (3)	0.0114 (2)	0.0111 (2)	0.0040 (2)	0.0052 (2)
N3B	0.0196 (3)	0.0211 (3)	0.0117 (2)	0.0072 (2)	0.00407 (19)	0.0047 (2)
C2B	0.0199 (3)	0.0173 (3)	0.0127 (3)	0.0063 (2)	0.0049 (2)	0.0057 (2)
C4B	0.0158 (3)	0.0187 (3)	0.0135 (3)	0.0040 (2)	0.0022 (2)	0.0052 (2)
C5B	0.0183 (3)	0.0195 (3)	0.0150 (3)	0.0066 (2)	0.0032 (2)	0.0051 (2)
C6B	0.0240 (3)	0.0224 (3)	0.0140 (3)	0.0114 (3)	0.0039 (2)	0.0045 (3)
C7B	0.0226 (4)	0.0280 (4)	0.0223 (4)	0.0122 (3)	0.0035 (3)	0.0075 (3)
C1'B	0.0259 (4)	0.0183 (3)	0.0124 (3)	0.0083 (3)	0.0033 (2)	0.0057 (2)
C2'B	0.0195 (3)	0.0200 (3)	0.0167 (3)	0.0041 (2)	0.0061 (2)	0.0070 (3)
C3'B	0.0188 (3)	0.0153 (3)	0.0147 (3)	0.0031 (2)	0.0038 (2)	0.0050 (2)
C4'B	0.0198 (3)	0.0177 (3)	0.0132 (3)	0.0034 (2)	0.0037 (2)	0.0070 (2)
C5'B	0.0260 (4)	0.0260 (4)	0.0165 (3)	0.0081 (3)	0.0058 (2)	0.0121 (3)

Geometric parameters (Å, º) top

O2A—C2A	1.2375 (11)	O2B—C2B	1.2399 (11)
O4A—C4A	1.2417 (11)	O4B—C4B	1.2411 (11)
O3'A—C3'A	1.4294 (12)	O3'B—C3'B	1.4387 (11)
O3'A—H3'A	0.83 (3)	O3'B—H3'B	0.84 (2)
O4'A—C1'A	1.4361 (11)	O4'B—C1'B	1.4257 (12)
O4'A—C4'A	1.4523 (10)	O4'B—C4'B	1.4514 (12)
O5'A—C5'A	1.4361 (12)	O5'B—C5'B	1.4276 (14)
O5'A—H5'A	0.84 (2)	O5'B—H5'B	0.72 (3)
N1A—C2A	1.3804 (10)	N1B—C2B	1.3790 (11)
N1A—C6A	1.3889 (11)	N1B—C6B	1.3916 (12)
N1A—C1'A	1.4788 (11)	N1B—C1'B	1.4889 (12)
N3A—C2A	1.3820 (11)	N3B—C2B	1.3817 (12)
N3A—C4A	1.3921 (12)	N3B—C4B	1.3928 (12)
N3A—H3A	0.874 (19)	N3B—H3B	0.857 (19)
C4A—C5A	1.4548 (12)	C4B—C5B	1.4555 (12)
C5A—C6A	1.3620 (11)	C5B—C6B	1.3576 (13)
C5A—C7A	1.5077 (13)	C5B—C7B	1.5058 (13)
C6A—H61A	0.9500	C6B—H61B	0.9500
C7A—H71A	0.9800	C7B—H71B	0.9800
C7A—H72A	0.9800	C7B—H72B	0.9800
C7A—H73A	0.9800	C7B—H73B	0.9800
C1'A—C2'A	1.5462 (12)	C1'B—C2'B	1.5479 (14)
C1'A—H11A	1.0000	C1'B—H11B	1.0000
C2'A—C3'A	1.5354 (13)	C2'B—C3'B	1.5385 (12)
C2'A—H21A	0.9900	C2'B—H21B	0.9900
C2'A—H22A	0.9900	C2'B—H22B	0.9900
C3'A—C4'A	1.5375 (13)	C3'B—C4'B	1.5337 (13)
C3'A—H31A	1.0000	C3'B—H31B	1.0000
C4'A—C5'A	1.5232 (11)	C4'B—C5'B	1.5247 (12)
C4'A—H41A	1.0000	C4'B—H41B	1.0000
C5'A—H51A	0.9900	C5'B—H51B	0.9900
C5'A—H52A	0.9900	C5'B—H52B	0.9900

C3'A—O3'A—H3'A	111.0 (18)	C3'B—O3'B—H3'B	103.1 (15)
C1'A—O4'A—C4'A	108.80 (6)	C1'B—O4'B—C4'B	110.33 (7)
C5'A—O5'A—H5'A	104.3 (15)	C5'B—O5'B—H5'B	106 (2)
C2A—N1A—C6A	121.45 (7)	C2B—N1B—C6B	121.11 (7)
C2A—N1A—C1'A	118.62 (7)	C2B—N1B—C1'B	119.38 (7)
C6A—N1A—C1'A	119.92 (6)	C6B—N1B—C1'B	119.39 (7)
C2A—N3A—C4A	126.74 (7)	C2B—N3B—C4B	126.93 (7)
C2A—N3A—H3A	111.5 (13)	C2B—N3B—H3B	109.8 (13)
C4A—N3A—H3A	121.7 (13)	C4B—N3B—H3B	123.1 (13)
O2A—C2A—N1A	123.23 (7)	O2B—C2B—N1B	123.42 (8)
O2A—C2A—N3A	121.66 (7)	O2B—C2B—N3B	121.40 (7)
N1A—C2A—N3A	115.11 (7)	N1B—C2B—N3B	115.17 (7)
O4A—C4A—N3A	119.13 (8)	O4B—C4B—N3B	119.09 (8)
O4A—C4A—C5A	125.35 (8)	O4B—C4B—C5B	125.55 (8)
N3A—C4A—C5A	115.52 (7)	N3B—C4B—C5B	115.36 (7)
C6A—C5A—C4A	117.91 (7)	C6B—C5B—C4B	117.81 (8)
C6A—C5A—C7A	123.05 (7)	C6B—C5B—C7B	123.27 (8)
C4A—C5A—C7A	119.04 (7)	C4B—C5B—C7B	118.92 (8)
C5A—C6A—N1A	123.11 (7)	C5B—C6B—N1B	123.55 (8)
C5A—C6A—H61A	118.4	C5B—C6B—H61B	118.2
N1A—C6A—H61A	118.4	N1B—C6B—H61B	118.2
C5A—C7A—H71A	109.5	C5B—C7B—H71B	109.5
C5A—C7A—H72A	109.5	C5B—C7B—H72B	109.5
H71A—C7A—H72A	109.5	H71B—C7B—H72B	109.5
C5A—C7A—H73A	109.5	C5B—C7B—H73B	109.5
H71A—C7A—H73A	109.5	H71B—C7B—H73B	109.5
H72A—C7A—H73A	109.5	H72B—C7B—H73B	109.5
O4'A—C1'A—N1A	107.00 (7)	O4'B—C1'B—N1B	107.95 (8)
O4'A—C1'A—C2'A	106.88 (6)	O4'B—C1'B—C2'B	107.49 (7)
N1A—C1'A—C2'A	114.23 (7)	N1B—C1'B—C2'B	113.28 (7)
O4'A—C1'A—H11A	109.5	O4'B—C1'B—H11B	109.3
N1A—C1'A—H11A	109.5	N1B—C1'B—H11B	109.3
C2'A—C1'A—H11A	109.5	C2'B—C1'B—H11B	109.3
C3'A—C2'A—C1'A	104.76 (7)	C3'B—C2'B—C1'B	104.46 (7)
C3'A—C2'A—H21A	110.8	C3'B—C2'B—H21B	110.9
C1'A—C2'A—H21A	110.8	C1'B—C2'B—H21B	110.9
C3'A—C2'A—H22A	110.8	C3'B—C2'B—H22B	110.9
C1'A—C2'A—H22A	110.8	C1'B—C2'B—H22B	110.9
H21A—C2'A—H22A	108.9	H21B—C2'B—H22B	108.9
O3'A—C3'A—C2'A	108.18 (7)	O3'B—C3'B—C4'B	107.56 (7)
O3'A—C3'A—C4'A	110.65 (8)	O3'B—C3'B—C2'B	112.97 (7)
C2'A—C3'A—C4'A	102.43 (7)	C4'B—C3'B—C2'B	103.19 (7)
O3'A—C3'A—H31A	111.7	O3'B—C3'B—H31B	110.9
C2'A—C3'A—H31A	111.7	C4'B—C3'B—H31B	110.9
C4'A—C3'A—H31A	111.7	C2'B—C3'B—H31B	110.9
O4'A—C4'A—C5'A	111.17 (7)	O4'B—C4'B—C5'B	111.39 (8)
O4'A—C4'A—C3'A	104.27 (6)	O4'B—C4'B—C3'B	105.66 (7)
C5'A—C4'A—C3'A	113.54 (7)	C5'B—C4'B—C3'B	113.17 (7)
O4'A—C4'A—H41A	109.2	O4'B—C4'B—H41B	108.8
C5'A—C4'A—H41A	109.2	C5'B—C4'B—H41B	108.8
C3'A—C4'A—H41A	109.2	C3'B—C4'B—H41B	108.8
O5'A—C5'A—C4'A	108.52 (7)	O5'B—C5'B—C4'B	109.34 (7)
O5'A—C5'A—H51A	110.0	O5'B—C5'B—H51B	109.8
C4'A—C5'A—H51A	110.0	C4'B—C5'B—H51B	109.8
O5'A—C5'A—H52A	110.0	O5'B—C5'B—H52B	109.8
C4'A—C5'A—H52A	110.0	C4'B—C5'B—H52B	109.8
H51A—C5'A—H52A	108.4	H51B—C5'B—H52B	108.3

C2A—N1A—C1'A—O4'A	124.84 (8)	C2B—N1B—C1'B—O4'B	123.87 (9)
C4'A—O4'A—C1'A—C2'A	17.59 (8)	C4'B—O4'B—C1'B—C2'B	8.61 (9)
O4'A—C1'A—C2'A—C3'A	5.50 (8)	O4'B—C1'B—C2'B—C3'B	10.72 (9)
C1'A—C2'A—C3'A—C4'A	−24.58 (8)	C1'B—C2'B—C3'B—C4'B	−24.45 (8)
C2'A—C3'A—C4'A—O4'A	35.38 (8)	C2'B—C3'B—C4'B—O4'B	30.05 (9)
C3'A—C4'A—O4'A—C1'A	−33.64 (8)	C3'B—C4'B—O4'B—C1'B	−24.65 (9)
O4'A—C4'A—C5'A—O5'A	59.34 (9)	O4'B—C4'B—C5'B—O5'B	−68.49 (10)
C6A—N1A—C2A—O2A	178.02 (8)	C6B—N1B—C2B—O2B	−179.61 (9)
C1'A—N1A—C2A—O2A	−3.22 (12)	C1'B—N1B—C2B—O2B	−3.66 (13)
C6A—N1A—C2A—N3A	−2.18 (11)	C6B—N1B—C2B—N3B	−0.55 (12)
C1'A—N1A—C2A—N3A	176.59 (7)	C1'B—N1B—C2B—N3B	175.39 (8)
C4A—N3A—C2A—O2A	−175.73 (9)	C4B—N3B—C2B—O2B	176.99 (9)
C4A—N3A—C2A—N1A	4.46 (12)	C4B—N3B—C2B—N1B	−2.09 (12)
C2A—N3A—C4A—O4A	177.70 (9)	C2B—N3B—C4B—O4B	−177.20 (9)
C2A—N3A—C4A—C5A	−2.87 (13)	C2B—N3B—C4B—C5B	3.35 (12)
O4A—C4A—C5A—C6A	178.33 (10)	O4B—C4B—C5B—C6B	178.62 (10)
N3A—C4A—C5A—C6A	−1.06 (12)	N3B—C4B—C5B—C6B	−1.96 (12)
O4A—C4A—C5A—C7A	−2.10 (14)	O4B—C4B—C5B—C7B	−0.63 (14)
N3A—C4A—C5A—C7A	178.51 (8)	N3B—C4B—C5B—C7B	178.79 (8)
C4A—C5A—C6A—N1A	3.14 (12)	C4B—C5B—C6B—N1B	−0.36 (14)
C7A—C5A—C6A—N1A	−176.41 (8)	C7B—C5B—C6B—N1B	178.86 (9)
C2A—N1A—C6A—C5A	−1.50 (12)	C2B—N1B—C6B—C5B	1.73 (14)
C1'A—N1A—C6A—C5A	179.75 (8)	C1'B—N1B—C6B—C5B	−174.21 (9)
C4'A—O4'A—C1'A—N1A	140.35 (6)	C4'B—O4'B—C1'B—N1B	131.14 (8)
C6A—N1A—C1'A—O4'A	−56.38 (9)	C6B—N1B—C1'B—O4'B	−60.12 (11)
C2A—N1A—C1'A—C2'A	−117.10 (8)	C2B—N1B—C1'B—C2'B	−117.23 (9)
C6A—N1A—C1'A—C2'A	61.68 (10)	C6B—N1B—C1'B—C2'B	58.79 (11)
N1A—C1'A—C2'A—C3'A	−112.64 (8)	N1B—C1'B—C2'B—C3'B	−108.45 (8)
C1'A—C2'A—C3'A—O3'A	92.32 (9)	C1'B—C2'B—C3'B—O3'B	91.40 (8)
C1'A—O4'A—C4'A—C5'A	89.07 (8)	C1'B—O4'B—C4'B—C5'B	98.63 (9)
O3'A—C3'A—C4'A—O4'A	−79.74 (8)	O3'B—C3'B—C4'B—O4'B	−89.59 (8)
O3'A—C3'A—C4'A—C5'A	159.11 (7)	O3'B—C3'B—C4'B—C5'B	148.27 (7)
C2'A—C3'A—C4'A—C5'A	−85.77 (8)	C2'B—C3'B—C4'B—C5'B	−92.09 (9)
C3'A—C4'A—C5'A—O5'A	176.54 (6)	C3'B—C4'B—C5'B—O5'B	50.39 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3′A—H3′A···O5′Aⁱ	0.83 (3)	2.00 (2)	2.7923 (14)	161 (3)
O5′A—H5′A···O4Aⁱⁱ	0.84 (2)	1.93 (2)	2.7546 (12)	170 (2)
N3A—H3A···O2Bⁱⁱⁱ	0.874 (19)	1.979 (19)	2.8531 (12)	177.9 (18)
C6A—H61A···O3′A	0.95	2.43	3.2371 (15)	143
O3′B—H3′B···O4′A^iv	0.84 (2)	2.09 (2)	2.9144 (12)	166 (2)
O5′B—H5′B···O4B^v	0.72 (3)	2.09 (3)	2.7893 (13)	162 (3)
N3B—H3B···O2A^vi	0.857 (19)	1.961 (19)	2.8078 (12)	169.7 (19)
C6B—H61B···O3′B	0.95	2.35	3.1682 (16)	144

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

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