Influence of fluorine substitution on the mol­ecular conformation of 3′-de­oxy-3′-fluoro-5-methyl­uridine

Fluorine substitutions on the furan­ose ring of nucleosides are known to strongly influence the conformational properties of oligonucleotides. In order to assess the effect of fluorine on the conformation of 3′-de­oxy-3′-fluoro-5-methyl­uridine (^RT^F), C₁₀H₁₃FN₂O₅, we studied its stereochemistry in the crystalline state using X-ray crystallography. The com­pound crystallizes in the chiral ortho­rhom­bic space group P2₁2₁2₁ and contains two symmetry-independent mol­ecules (A and B) in the asymmetric unit. The furan­ose ring in mol­ecules A and B adopts conformations between envelope (²E, 2′-endo, P = 162°) and twisted (²T₃, 2′-endo and 3′exo, P = 180°), with pseudorotation phase angles (P) of 164.3 and 170.2°, respectively. The maximum puckering amplitudes, ν_max, for mol­ecules A and B are 38.8 and 36.1°, respectively. In contrast, for 5-methyl­uridine (^RT^OH), the value of P is 21.2°, which is between the ³E (3′-endo, P = 18.0°) and ³T₄ (3′-endo and 4′-exo, P = 36°) conformations. The value of ν_max for ^RT^OH is 41.29°. Mol­ecules A and B of ^RT^F generate respective helical assemblies across the crystal­lographic 2₁-screw axis through classical N—H...O aand O—H...O hydro­gen bonds supplemented by C—H...O contacts. Adjacent parallel helices of both mol­ecules are linked to each other via O—H...O and O...π inter­actions.

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXTL (Bruker, 2006), PLATON (Spek, 2020) and publCIF (Westrip, 2010).

3'-Fluoro-3'-deoxy-5-methyluridine

Crystal data

C10H13FN2O5	Dx = 1.520 Mg m^−3
Mr = 260.22	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9902 reflections
a = 7.0301 (3) Å	θ = 2.5–30.9°
b = 17.1705 (8) Å	µ = 0.13 mm^−1
c = 18.8369 (9) Å	T = 296 K
V = 2273.81 (18) Å^3	Plate, colourless
Z = 8	0.40 × 0.30 × 0.22 mm
F(000) = 1088

Data collection

Bruker APEXII CCD diffractometer	4002 independent reflections
Radiation source: Fine focus sealed tube	3837 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −7→8
Tmin = 0.949, Tmax = 0.972	k = −20→20
31022 measured reflections	l = −22→22

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0307P)^2 + 0.4954P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.067	(Δ/σ)max = 0.001
S = 1.10	Δρmax = 0.13 e Å^−3
4002 reflections	Δρmin = −0.14 e Å^−3
351 parameters	Absolute structure: Flack x determined using 1541 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.0 (2)

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.

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

	x	y	z	Uiso*/Ueq
F3'	−0.0060 (2)	0.65373 (10)	0.70579 (7)	0.0464 (4)
F3''	0.2654 (2)	0.32166 (9)	1.06606 (7)	0.0422 (4)
O2A	−0.0021 (3)	0.54059 (10)	0.95157 (9)	0.0391 (4)
O4A	0.4226 (3)	0.63184 (11)	1.11204 (8)	0.0374 (4)
O2'	−0.0442 (3)	0.71961 (13)	0.83490 (10)	0.0401 (5)
O4'	0.3141 (3)	0.58196 (9)	0.79074 (8)	0.0346 (4)
O5'	0.5620 (3)	0.71432 (13)	0.77067 (12)	0.0520 (6)
O2''	0.3545 (3)	0.24214 (10)	0.94469 (9)	0.0363 (4)
O4''	0.4260 (3)	0.44496 (9)	0.96731 (8)	0.0336 (4)
O5''	0.8193 (3)	0.40864 (11)	1.00190 (11)	0.0455 (5)
O2B	0.1154 (3)	0.34758 (13)	0.81722 (10)	0.0484 (5)
O4B	0.5120 (3)	0.44644 (13)	0.65023 (9)	0.0514 (5)
N1A	0.2535 (3)	0.60931 (11)	0.91032 (9)	0.0260 (4)
N3A	0.2127 (3)	0.58861 (11)	1.03050 (10)	0.0273 (4)
N1B	0.4065 (3)	0.39216 (11)	0.85359 (9)	0.0286 (4)
N3B	0.3184 (3)	0.39792 (12)	0.73551 (11)	0.0333 (5)
C1'	0.1779 (4)	0.61286 (13)	0.83765 (11)	0.0273 (5)
H1'	0.0609	0.5820	0.8348	0.033*
C2'	0.1380 (3)	0.69566 (14)	0.81246 (12)	0.0270 (5)
H2'1	0.2348	0.7312	0.8311	0.032*
C3'	0.1608 (4)	0.68712 (15)	0.73269 (12)	0.0314 (5)
H3'	0.1914	0.7367	0.7096	0.038*
C4'	0.3208 (4)	0.62813 (15)	0.72601 (12)	0.0348 (6)
H4'	0.2923	0.5938	0.6858	0.042*
C5'	0.5168 (4)	0.66062 (19)	0.71579 (15)	0.0471 (7)
H5'1	0.6087	0.6185	0.7159	0.057*
H5'2	0.5241	0.6866	0.6702	0.057*
C1''	0.3606 (4)	0.37925 (13)	0.92824 (11)	0.0283 (5)
H1''	0.2224	0.3747	0.9336	0.034*
C2''	0.4553 (3)	0.30963 (13)	0.96250 (12)	0.0264 (5)
H2'2	0.5871	0.3053	0.9461	0.032*
C3''	0.4514 (3)	0.33313 (14)	1.03996 (12)	0.0281 (5)
H3''	0.5469	0.3053	1.0681	0.034*
C4''	0.4890 (4)	0.41983 (14)	1.03721 (12)	0.0300 (5)
H4''	0.4081	0.4451	1.0728	0.036*
C5''	0.6911 (4)	0.44507 (15)	1.04993 (14)	0.0400 (6)
H5'3	0.7000	0.5011	1.0446	0.048*
H5'4	0.7272	0.4321	1.0982	0.048*
C2A	0.1451 (3)	0.57611 (12)	0.96287 (12)	0.0262 (5)
C4A	0.3810 (3)	0.62377 (13)	1.04851 (11)	0.0269 (5)
C5A	0.4990 (4)	0.64899 (13)	0.99056 (12)	0.0270 (5)
C6A	0.4285 (3)	0.64152 (13)	0.92457 (12)	0.0261 (5)
H6A	0.5017	0.6590	0.8867	0.031*
C7A	0.6878 (4)	0.68522 (17)	1.00607 (14)	0.0397 (6)
H7A1	0.6690	0.7355	1.0272	0.060*
H7A2	0.7582	0.6908	0.9627	0.060*
H7A3	0.7574	0.6526	1.0383	0.060*
C2B	0.2677 (4)	0.37686 (14)	0.80336 (12)	0.0324 (6)
C4B	0.4890 (4)	0.42850 (14)	0.71324 (12)	0.0342 (6)
C5B	0.6317 (4)	0.43750 (14)	0.76744 (12)	0.0306 (5)
C6B	0.5841 (4)	0.41923 (14)	0.83428 (12)	0.0302 (5)
H6B	0.6756	0.4251	0.8695	0.036*
C7B	0.8240 (4)	0.46819 (19)	0.74696 (14)	0.0449 (7)
H7B1	0.9086	0.4645	0.7868	0.067*
H7B2	0.8128	0.5217	0.7327	0.067*
H7B3	0.8737	0.4380	0.7083	0.067*
H2'	−0.032 (6)	0.766 (3)	0.846 (2)	0.086 (15)*
H5'	0.683 (6)	0.718 (2)	0.7765 (19)	0.072 (12)*
H5"	0.886 (6)	0.447 (2)	0.9857 (19)	0.072 (11)*
H2"	0.394 (5)	0.2046 (18)	0.9643 (17)	0.051 (10)*
H3A	0.145 (4)	0.5732 (15)	1.0667 (14)	0.033 (7)*
H3B	0.238 (4)	0.3889 (16)	0.7024 (15)	0.037 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F3'	0.0397 (9)	0.0693 (11)	0.0304 (8)	−0.0070 (8)	−0.0089 (7)	−0.0016 (7)
F3''	0.0366 (8)	0.0567 (9)	0.0334 (8)	−0.0118 (8)	0.0116 (7)	−0.0027 (7)
O2A	0.0385 (10)	0.0487 (11)	0.0303 (9)	−0.0193 (9)	−0.0006 (8)	0.0059 (7)
O4A	0.0423 (11)	0.0502 (11)	0.0197 (8)	−0.0066 (9)	−0.0031 (7)	−0.0024 (7)
O2'	0.0327 (11)	0.0468 (12)	0.0408 (10)	0.0055 (9)	0.0057 (8)	−0.0037 (9)
O4'	0.0489 (11)	0.0326 (9)	0.0225 (8)	0.0082 (8)	0.0030 (8)	−0.0011 (7)
O5'	0.0356 (13)	0.0657 (14)	0.0545 (13)	−0.0093 (11)	0.0059 (10)	0.0002 (10)
O2''	0.0455 (11)	0.0275 (9)	0.0358 (10)	−0.0050 (8)	−0.0042 (9)	0.0004 (8)
O4''	0.0496 (11)	0.0264 (8)	0.0248 (8)	0.0038 (8)	−0.0029 (8)	−0.0003 (6)
O5''	0.0379 (11)	0.0356 (10)	0.0632 (13)	−0.0074 (9)	0.0081 (10)	0.0077 (9)
O2B	0.0380 (11)	0.0674 (13)	0.0396 (10)	−0.0161 (10)	−0.0076 (9)	0.0118 (9)
O4B	0.0554 (13)	0.0769 (14)	0.0220 (9)	−0.0188 (11)	−0.0056 (9)	0.0083 (9)
N1A	0.0277 (11)	0.0294 (10)	0.0209 (9)	−0.0052 (9)	−0.0015 (8)	0.0017 (7)
N3A	0.0314 (11)	0.0328 (10)	0.0178 (9)	−0.0054 (9)	0.0048 (9)	0.0022 (8)
N1B	0.0298 (11)	0.0348 (11)	0.0212 (9)	−0.0007 (9)	−0.0031 (8)	0.0039 (8)
N3B	0.0375 (13)	0.0390 (12)	0.0235 (10)	−0.0067 (10)	−0.0100 (10)	0.0010 (9)
C1'	0.0313 (13)	0.0312 (12)	0.0195 (10)	−0.0054 (10)	−0.0020 (10)	−0.0006 (9)
C2'	0.0246 (12)	0.0322 (12)	0.0242 (11)	0.0012 (10)	0.0001 (10)	−0.0001 (9)
C3'	0.0321 (13)	0.0384 (13)	0.0238 (12)	−0.0048 (11)	−0.0041 (10)	0.0033 (10)
C4'	0.0440 (15)	0.0427 (14)	0.0178 (11)	0.0011 (12)	0.0019 (11)	−0.0011 (10)
C5'	0.0422 (17)	0.0657 (19)	0.0335 (14)	0.0066 (15)	0.0118 (13)	0.0064 (13)
C1''	0.0291 (13)	0.0318 (12)	0.0241 (11)	0.0018 (11)	0.0023 (10)	0.0015 (9)
C2''	0.0275 (13)	0.0263 (11)	0.0253 (11)	0.0002 (10)	0.0019 (10)	−0.0001 (9)
C3''	0.0240 (12)	0.0374 (13)	0.0228 (11)	−0.0027 (10)	0.0016 (10)	0.0045 (10)
C4''	0.0366 (14)	0.0332 (13)	0.0203 (11)	0.0032 (11)	0.0032 (11)	−0.0013 (9)
C5''	0.0481 (17)	0.0346 (13)	0.0372 (14)	−0.0100 (12)	−0.0050 (13)	0.0004 (11)
C2A	0.0294 (13)	0.0246 (11)	0.0246 (11)	−0.0031 (10)	0.0026 (10)	0.0036 (9)
C4A	0.0325 (13)	0.0257 (11)	0.0224 (11)	0.0030 (10)	0.0003 (10)	0.0000 (9)
C5A	0.0290 (12)	0.0271 (12)	0.0250 (11)	−0.0010 (10)	0.0000 (10)	−0.0018 (9)
C6A	0.0277 (13)	0.0273 (11)	0.0234 (11)	−0.0036 (10)	0.0045 (10)	0.0028 (9)
C7A	0.0335 (15)	0.0507 (15)	0.0350 (14)	−0.0094 (12)	−0.0002 (12)	−0.0019 (12)
C2B	0.0361 (15)	0.0319 (12)	0.0293 (12)	−0.0002 (12)	−0.0080 (11)	0.0040 (10)
C4B	0.0406 (15)	0.0356 (13)	0.0265 (12)	−0.0022 (12)	−0.0038 (11)	−0.0007 (10)
C5B	0.0311 (13)	0.0334 (12)	0.0273 (12)	0.0016 (11)	−0.0029 (11)	0.0004 (10)
C6B	0.0299 (13)	0.0352 (13)	0.0256 (12)	0.0021 (11)	−0.0066 (10)	0.0012 (10)
C7B	0.0360 (16)	0.0607 (18)	0.0378 (15)	−0.0011 (14)	−0.0020 (12)	0.0085 (13)

Geometric parameters (Å, º)

F3'—C3'	1.400 (3)	C2'—C3'	1.518 (3)
F3''—C3''	1.411 (3)	C2'—H2'1	0.9800
O2A—C2A	1.220 (3)	C3'—C4'	1.519 (4)
O4A—C4A	1.240 (3)	C3'—H3'	0.9800
O2'—C2'	1.410 (3)	C4'—C5'	1.499 (4)
O2'—H2'	0.83 (4)	C4'—H4'	0.9800
O4'—C1'	1.407 (3)	C5'—H5'1	0.9700
O4'—C4'	1.455 (3)	C5'—H5'2	0.9700
O5'—C5'	1.421 (4)	C1''—C2''	1.513 (3)
O5'—H5'	0.86 (4)	C1''—H1''	0.9800
O2''—C2''	1.399 (3)	C2''—C3''	1.514 (3)
O2''—H2"	0.79 (3)	C2''—H2'2	0.9800
O4''—C1''	1.423 (3)	C3''—C4''	1.513 (3)
O4''—C4''	1.455 (3)	C3''—H3''	0.9800
O5''—C5''	1.422 (3)	C4''—C5''	1.505 (4)
O5''—H5"	0.87 (4)	C4''—H4''	0.9800
O2B—C2B	1.212 (3)	C5''—H5'3	0.9700
O4B—C4B	1.237 (3)	C5''—H5'4	0.9700
N1A—C2A	1.373 (3)	C4A—C5A	1.438 (3)
N1A—C6A	1.376 (3)	C5A—C6A	1.344 (3)
N1A—C1'	1.470 (3)	C5A—C7A	1.494 (4)
N3A—C4A	1.371 (3)	C6A—H6A	0.9300
N3A—C2A	1.376 (3)	C7A—H7A1	0.9600
N3A—H3A	0.87 (3)	C7A—H7A2	0.9600
N1B—C6B	1.381 (3)	C7A—H7A3	0.9600
N1B—C2B	1.384 (3)	C4B—C5B	1.440 (3)
N1B—C1''	1.460 (3)	C5B—C6B	1.340 (3)
N3B—C4B	1.374 (3)	C5B—C7B	1.502 (4)
N3B—C2B	1.375 (3)	C6B—H6B	0.9300
N3B—H3B	0.85 (3)	C7B—H7B1	0.9600
C1'—C2'	1.525 (3)	C7B—H7B2	0.9600
C1'—H1'	0.9800	C7B—H7B3	0.9600
C2'—O2'—H2'	105 (3)	O2''—C2''—H2'2	109.9
C1'—O4'—C4'	110.06 (18)	C1''—C2''—H2'2	109.9
C5'—O5'—H5'	111 (3)	C3''—C2''—H2'2	109.9
C2''—O2''—H2"	113 (2)	F3''—C3''—C4''	108.12 (19)
C1''—O4''—C4''	109.33 (17)	F3''—C3''—C2''	108.37 (19)
C5''—O5''—H5"	103 (2)	C4''—C3''—C2''	103.07 (18)
C2A—N1A—C6A	121.50 (19)	F3''—C3''—H3''	112.3
C2A—N1A—C1'	119.22 (19)	C4''—C3''—H3''	112.3
C6A—N1A—C1'	119.24 (18)	C2''—C3''—H3''	112.3
C4A—N3A—C2A	126.6 (2)	O4''—C4''—C5''	110.2 (2)
C4A—N3A—H3A	114.2 (18)	O4''—C4''—C3''	105.65 (18)
C2A—N3A—H3A	119.2 (18)	C5''—C4''—C3''	116.3 (2)
C6B—N1B—C2B	121.41 (19)	O4''—C4''—H4''	108.1
C6B—N1B—C1''	120.32 (19)	C5''—C4''—H4''	108.1
C2B—N1B—C1''	118.3 (2)	C3''—C4''—H4''	108.1
C4B—N3B—C2B	127.6 (2)	O5''—C5''—C4''	111.7 (2)
C4B—N3B—H3B	114.9 (18)	O5''—C5''—H5'3	109.3
C2B—N3B—H3B	117.4 (19)	C4''—C5''—H5'3	109.3
O4'—C1'—N1A	108.87 (19)	O5''—C5''—H5'4	109.3
O4'—C1'—C2'	106.35 (18)	C4''—C5''—H5'4	109.3
N1A—C1'—C2'	113.26 (18)	H5'3—C5''—H5'4	107.9
O4'—C1'—H1'	109.4	O2A—C2A—N1A	123.5 (2)
N1A—C1'—H1'	109.4	O2A—C2A—N3A	122.2 (2)
C2'—C1'—H1'	109.4	N1A—C2A—N3A	114.3 (2)
O2'—C2'—C3'	114.9 (2)	O4A—C4A—N3A	119.5 (2)
O2'—C2'—C1'	110.2 (2)	O4A—C4A—C5A	124.3 (2)
C3'—C2'—C1'	101.45 (18)	N3A—C4A—C5A	116.27 (19)
O2'—C2'—H2'1	110.0	C6A—C5A—C4A	117.4 (2)
C3'—C2'—H2'1	110.0	C6A—C5A—C7A	123.2 (2)
C1'—C2'—H2'1	110.0	C4A—C5A—C7A	119.3 (2)
F3'—C3'—C2'	108.0 (2)	C5A—C6A—N1A	123.3 (2)
F3'—C3'—C4'	108.5 (2)	C5A—C6A—H6A	118.4
C2'—C3'—C4'	102.97 (19)	N1A—C6A—H6A	118.4
F3'—C3'—H3'	112.3	C5A—C7A—H7A1	109.5
C2'—C3'—H3'	112.3	C5A—C7A—H7A2	109.5
C4'—C3'—H3'	112.3	H7A1—C7A—H7A2	109.5
O4'—C4'—C5'	109.9 (2)	C5A—C7A—H7A3	109.5
O4'—C4'—C3'	105.65 (19)	H7A1—C7A—H7A3	109.5
C5'—C4'—C3'	116.3 (2)	H7A2—C7A—H7A3	109.5
O4'—C4'—H4'	108.2	O2B—C2B—N3B	122.6 (2)
C5'—C4'—H4'	108.2	O2B—C2B—N1B	123.7 (2)
C3'—C4'—H4'	108.2	N3B—C2B—N1B	113.7 (2)
O5'—C5'—C4'	110.7 (2)	O4B—C4B—N3B	120.1 (2)
O5'—C5'—H5'1	109.5	O4B—C4B—C5B	124.3 (3)
C4'—C5'—H5'1	109.5	N3B—C4B—C5B	115.6 (2)
O5'—C5'—H5'2	109.5	C6B—C5B—C4B	117.9 (2)
C4'—C5'—H5'2	109.5	C6B—C5B—C7B	123.2 (2)
H5'1—C5'—H5'2	108.1	C4B—C5B—C7B	118.9 (2)
O4''—C1''—N1B	107.83 (18)	C5B—C6B—N1B	123.5 (2)
O4''—C1''—C2''	105.30 (18)	C5B—C6B—H6B	118.3
N1B—C1''—C2''	115.69 (19)	N1B—C6B—H6B	118.3
O4''—C1''—H1''	109.3	C5B—C7B—H7B1	109.5
N1B—C1''—H1''	109.3	C5B—C7B—H7B2	109.5
C2''—C1''—H1''	109.3	H7B1—C7B—H7B2	109.5
O2''—C2''—C1''	109.23 (19)	C5B—C7B—H7B3	109.5
O2''—C2''—C3''	116.28 (19)	H7B1—C7B—H7B3	109.5
C1''—C2''—C3''	101.10 (18)	H7B2—C7B—H7B3	109.5
C4'—O4'—C1'—N1A	−139.95 (19)	F3''—C3''—C4''—O4''	−89.4 (2)
C4'—O4'—C1'—C2'	−17.6 (2)	C2''—C3''—C4''—O4''	25.2 (2)
C2A—N1A—C1'—O4'	−128.7 (2)	F3''—C3''—C4''—C5''	148.0 (2)
C6A—N1A—C1'—O4'	53.4 (3)	C2''—C3''—C4''—C5''	−97.4 (2)
C2A—N1A—C1'—C2'	113.2 (2)	O4''—C4''—C5''—O5''	−64.1 (3)
C6A—N1A—C1'—C2'	−64.7 (3)	C3''—C4''—C5''—O5''	56.1 (3)
O4'—C1'—C2'—O2'	155.48 (18)	C6A—N1A—C2A—O2A	−172.9 (2)
N1A—C1'—C2'—O2'	−85.0 (2)	C1'—N1A—C2A—O2A	9.2 (3)
O4'—C1'—C2'—C3'	33.3 (2)	C6A—N1A—C2A—N3A	9.4 (3)
N1A—C1'—C2'—C3'	152.9 (2)	C1'—N1A—C2A—N3A	−168.5 (2)
O2'—C2'—C3'—F3'	−39.8 (3)	C4A—N3A—C2A—O2A	176.0 (2)
C1'—C2'—C3'—F3'	79.1 (2)	C4A—N3A—C2A—N1A	−6.2 (3)
O2'—C2'—C3'—C4'	−154.5 (2)	C2A—N3A—C4A—O4A	179.2 (2)
C1'—C2'—C3'—C4'	−35.6 (2)	C2A—N3A—C4A—C5A	−0.9 (3)
C1'—O4'—C4'—C5'	120.6 (2)	O4A—C4A—C5A—C6A	−175.1 (2)
C1'—O4'—C4'—C3'	−5.7 (3)	N3A—C4A—C5A—C6A	5.0 (3)
F3'—C3'—C4'—O4'	−87.9 (2)	O4A—C4A—C5A—C7A	2.0 (4)
C2'—C3'—C4'—O4'	26.4 (2)	N3A—C4A—C5A—C7A	−177.8 (2)
F3'—C3'—C4'—C5'	149.9 (2)	C4A—C5A—C6A—N1A	−1.9 (3)
C2'—C3'—C4'—C5'	−95.8 (2)	C7A—C5A—C6A—N1A	−178.9 (2)
O4'—C4'—C5'—O5'	−65.2 (3)	C2A—N1A—C6A—C5A	−5.8 (3)
C3'—C4'—C5'—O5'	54.8 (3)	C1'—N1A—C6A—C5A	172.1 (2)
C4''—O4''—C1''—N1B	−146.43 (18)	C4B—N3B—C2B—O2B	−177.2 (3)
C4''—O4''—C1''—C2''	−22.4 (2)	C4B—N3B—C2B—N1B	2.7 (4)
C6B—N1B—C1''—O4''	45.4 (3)	C6B—N1B—C2B—O2B	174.2 (2)
C2B—N1B—C1''—O4''	−134.4 (2)	C1''—N1B—C2B—O2B	−6.1 (4)
C6B—N1B—C1''—C2''	−72.2 (3)	C6B—N1B—C2B—N3B	−5.7 (3)
C2B—N1B—C1''—C2''	108.1 (2)	C1''—N1B—C2B—N3B	174.0 (2)
O4''—C1''—C2''—O2''	160.26 (19)	C2B—N3B—C4B—O4B	−178.2 (3)
N1B—C1''—C2''—O2''	−80.8 (2)	C2B—N3B—C4B—C5B	1.6 (4)
O4''—C1''—C2''—C3''	37.2 (2)	O4B—C4B—C5B—C6B	176.8 (3)
N1B—C1''—C2''—C3''	156.1 (2)	N3B—C4B—C5B—C6B	−3.1 (3)
O2''—C2''—C3''—F3''	−41.1 (3)	O4B—C4B—C5B—C7B	−2.0 (4)
C1''—C2''—C3''—F3''	77.0 (2)	N3B—C4B—C5B—C7B	178.1 (2)
O2''—C2''—C3''—C4''	−155.5 (2)	C4B—C5B—C6B—N1B	0.2 (4)
C1''—C2''—C3''—C4''	−37.4 (2)	C7B—C5B—C6B—N1B	178.9 (2)
C1''—O4''—C4''—C5''	124.5 (2)	C2B—N1B—C6B—C5B	4.5 (4)
C1''—O4''—C4''—C3''	−1.9 (2)	C1''—N1B—C6B—C5B	−175.2 (2)

Hydrogen-bond geometry (Å, º)

Cg2 is the centroid of the N1A/C2A/N3A/C4A–C6A ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···O4B^i	0.87 (3)	1.95 (3)	2.818 (3)	172 (2)
N3B^ii—H3B^ii···O4A	0.85 (3)	2.08 (3)	2.923 (3)	172 (3)
O5′—H5′···O2′^iii	0.86 (4)	2.21 (4)	3.022 (3)	157 (3)
O2′—H2′···O4A^iv	0.83 (4)	1.95 (4)	2.749 (3)	161 (4)
O2"—H2"···O5"^v	0.79 (3)	2.11 (3)	2.789 (3)	143 (3)
O5"—H5"···O2A^iii	0.87 (4)	1.90 (4)	2.758 (3)	172 (4)
C7B—H7B3···O4A^vi	0.96	2.60	3.547 (3)	168
C7B—H7B1···O2B^iii	0.96	2.54	3.199 (4)	126
C3"—H3"···O2"^vii	0.98	2.32	3.128 (3)	139
C2"—H2′2···F3"^vii	0.98	2.53	3.182 (3)	124
C7A—H7A1···Cg2^viii	0.96	2.78	3.571 (3)	140

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