3-[4-(3,4-Di­methyl­phenyl)-1,3-thia­zol-2-yl]-2-(2-hydroxy­phenyl)-1,2,3,4-tetra­hydro­quin­az­olin-4-one

The facile one-pot synthesis of the title compound, C₂₅H₂₁N₃O₂S, is described. The six-membered 1,3-di­aza ring is puckered with an axial phenyl group in the 2-position. Intermolecular hydrogen bonding between hydroxyl and ketonic O atoms produces infinite one-dimensional chains in the a direction.

S1. Comment

4-(1H)-Quinazolinones, commonly known as benzpyrimidinones, form an important class of heterocyclic compounds. Some of them either occur as quinazoline alkaloids (Mohrle & Gundlack, 1970; Baker & McEvoy, 1995) or their precursors (Brown, 1984). In addition, numerous synthetic quinazolinone derivatives are known which exhibit diverse antihistamic (Graham, 1960), diuretic (Cohen et al., 1960), hypnotic (Chappel & Seeman, 1963) and anti-inflammatory (Saravanan et al., 1998) biological activities.

In view of the multifaceted pharmacological behaviour of this class of heterocyclic compounds, an attempt was made to synthesize some new 2,3-disubstituted-benzpyrimidones, containing three different biodynamic moieties. For this purpose, synthesis of the title compound, (IV), was anticipated starting from the key intermediate (III) which in turn might be obtained by condensing 2-amino-4-(3,4-dimethylphenyl)thiazole, (I), with N-(2-hydrpoxybenzylidine)-anthranilic acid, (II), in the presence of phosphorus oxychloride. When this reaction was carried out, (IV) was obtained directly, rather than the expected amide (III). The direct formation of (IV) might be explained on the basis that the condensation and cyclization take place in a concerted manner with the final stage involving the facile nucleophilic attack of the amidic nitrogen on the benzylidene carbon. Crystals of (IV) were recrystallized from a mixture of DMF-C₂H₅OH and its structure was finally confirmed by single-crystal X-ray diffraction. \sch

The molecular structure of the title compound is illustrated in Fig. 1. The bond lengths and angles are largely unremarkable, although the C5'-S1'-C2' bond angle of 87.98 (9)° is perhaps slightly narrower than expected; a survey of the Cambridge Structural Database (Allen & Kennard, 1993) for 1,3-thiazol rings gave a mean (based upon 1906 observations) value of 90.79 (5)° for this angle. The thiazole ring is flat (r.m.s. deviation 0.005 Å) and is inclined at an angle of 32.7 (1)° to the plane of the attached phenyl group. The 1,3-diaza ring, containing an sp³ carbon atom (i.e. C2), is non-planar with Cremer-Pople puckering parameters (Cremer & Pople, 1975) of Q_T = 0.418 (2) Å, θ = 61.9 (3)° and ϕ = 44.9 (3)°; the only axial substituent attached to this ring is the hydroxyphenyl group which is inclined at an angle of 86.1 (1)° with respect to the best plane through the diaza ring (r.m.s. deviation 0.0171 Å).

The intramolecular O1···S1' contact of 2.6138 (14) Å is short in comparison to the sum of the van der Waals radii for O and S (3.32 Å): it arises from the planarity of the O1═C4—N3—C2'—S1' unit (see the appropriate torsion angles in Table 1), an arrangement which minimizes the O···S separation. This planarity is anticipated on the basis of resonance theory which predicts partial double bond character in the N3—C4 and N3–C2' bonds, resulting in restricted rotation about these linkages.

Infinite one-dimensional chains are formed via hydrogen bonding between hydroxyl groups (O2—H) and ketonic O atoms (O1) in the a direction; these O.·O distances of 2.7682 (18) Å are significantly shorter than the sum of the oxygen van der Waals radii (3.04 Å; Bondi, 1964). A weaker intra-molecular hydrogen-bonding interaction between the N1 hydrogen atom and the O2 atom is also present.

S2. Experimental

A mixture of 2-amino-4-(3,4-dimethylphenyl)thiazole (1.0 g, 0.005 mol) and n-(2-hydroxybenzylidene)anthranilic acid (1.2 g, 0.005 mol) in freshly distilled phosphorus oxychloride (40 ml) was refluxed for 8 hrs. The progress of the reaction was monitored by thin-layer chromatography. After completion of the reaction, the contents were cooled and poured into ice-water. The solid that separated was filtered, washed with water, dried and crystallized from a mixture of DMF-C₂H₅OH as pale yellow needles (1.7 g, 81% yield, m.p. 502 K). IR(KBr)ν_max: 3320, 3030, 2960, 1735, 1698, 1615, 1576, 1419, 1402, 1382, 1297, 1263, 1142, 1089, 1060, 990, 890, 820, 760 cm^{-1. 1}H NMR (250 MHz, DMSO-d₆): δ 2.22 and 2.51 (2 s, 3H each, 2 x CH₃), 6.59 (m, 1H, H-3''), 6.73–6.82 (m, 2H, H-8 and H-4''), 6.85–6.91 (m, 2H, H-5'' and H-2'''), 7.02–7.15 (m, 2H, H-6 and H-5'''), 7.32 (m, 1H, H-7), 7.54–7.69 (m, 4H, H-2, H-5', H-6'' and H-6'''), 7.86 (dd, 1H, J = 7.9 and 1.5 Hz, H-5), 10.2 (s, 1H, NH). ¹³C NMR (62.9 MHz, DMSO-d₆): δ 19.0, 19.4, 65.0, 108.8, 112.7, 115.3, 115.5, 117.7, 118.4, 123.0, 125.1, 125.9, 126.7, 127.8, 129.2, 129.6, 131.6, 134.8, 135.8, 136.2, 146.4, 148.3, 154.6, 156.4, 161.4. EIMS m/z (% int): 427(M⁺, 38), 333 (16), 308 (12), 275 (13), 243 (18), 239 (85), 238 (38), 224 (30), 204 (26), 199 (20), 180 (18), 158 (100), 105 (14), 91 (30), 86 (34) and 69 (19).

S3. Refinement

H atoms bonded to N, O and methyl C atoms were located from ΔF syntheses, while others bound to C atoms were placed geometrically. For refinement those bonded to N and O atoms were refined freely, those in CH₃ groups were treated as part of rigid rotating groups with U_iso(H) = 1.5U_eq(C) and other H atoms bound to C were constrained to ride on these carrier atoms with U_iso(H) = 1.2U_eq(C).

Computing details

Data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Siemens, 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC; software used to prepare material for publication: SHELXTL/PC.

Figures

Fig. 1. View of the molecule showing the atomic numbering. Displacement ellipsoids are drawn at the 50% probability level for non-H atoms. Hydrogen atoms are shown as spheres of arbitrary radii.

(IV)

Crystal data

C25H21N3O2S	Z = 2
Mr = 427.51	F(000) = 448
Triclinic, P1	Dx = 1.384 Mg m^−3
a = 8.9439 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5231 (12) Å	Cell parameters from 3730 reflections
c = 12.0135 (12) Å	θ = 2.0–28.6°
α = 63.663 (3)°	µ = 0.19 mm^−1
β = 68.248 (3)°	T = 180 K
γ = 75.966 (3)°	Block, yellow
V = 1026.06 (18) Å^3	0.42 × 0.32 × 0.10 mm

Data collection

Siemens SMART CCD area detector diffractometer with Oxford Cryosystems open-flow cryostat (Cosier & Glazer, 1986)	4545 independent reflections
Radiation source: normal-focus sealed tube	3162 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.192 pixels mm^-1	θmax = 28.6°, θmin = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→9
Tmin = 0.926, Tmax = 0.982	l = −15→14
6303 measured 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0603P)^2] where P = (Fo^2 + 2Fc^2)/3
4545 reflections	(Δ/σ)max < 0.001
294 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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. The temperature of the crystal was controlled using the Oxford Cryosystem Cryostream Cooler (Cosier & Glazer, 1986).

Data were collected over a hemisphere of reciprocal space, by a combination of three sets of exposures. Each set had a different ϕ angle for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal to detector distance was 5.01 cm. Crystal decay was monitored by repeating the initial frames at the end of the data collection and analyzing the duplicate reflections.

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

	x	y	z	Uiso*/Ueq
S1'	0.90489 (5)	0.27276 (5)	0.36923 (5)	0.03164 (15)
O1	0.80359 (14)	0.12134 (13)	0.61581 (13)	0.0340 (3)
O2	1.51436 (16)	0.08272 (14)	0.60838 (15)	0.0385 (4)
H2"B	1.599 (3)	0.091 (3)	0.617 (3)	0.083 (9)*
N1	1.23189 (19)	−0.04198 (16)	0.67536 (15)	0.0289 (4)
H1A	1.318 (2)	−0.070 (2)	0.6880 (19)	0.037 (6)*
N3	1.07767 (16)	0.10911 (14)	0.53902 (13)	0.0233 (3)
N3'	1.21346 (17)	0.21290 (14)	0.31535 (14)	0.0252 (3)
C2	1.23302 (19)	0.08345 (17)	0.56794 (17)	0.0230 (4)
H2A	1.3231	0.0781	0.4899	0.028*
C4	0.9345 (2)	0.08049 (18)	0.63918 (17)	0.0261 (4)
C5	0.8102 (2)	−0.0259 (2)	0.87810 (19)	0.0377 (5)
H5A	0.7080	0.0157	0.8672	0.045*
C6	0.8202 (3)	−0.1089 (2)	0.9997 (2)	0.0509 (6)
H6A	0.7260	−0.1239	1.0731	0.061*
C7	0.9694 (3)	−0.1708 (2)	1.0144 (2)	0.0531 (6)
H7A	0.9763	−0.2292	1.0986	0.064*
C8	1.1082 (3)	−0.1495 (2)	0.90920 (19)	0.0421 (5)
H8A	1.2092	−0.1932	0.9212	0.051*
C9	1.0994 (2)	−0.06334 (18)	0.78526 (17)	0.0290 (4)
C10	0.9486 (2)	−0.00147 (18)	0.76949 (17)	0.0279 (4)
C2'	1.0785 (2)	0.19046 (17)	0.41052 (17)	0.0239 (4)
C4'	1.1834 (2)	0.30132 (18)	0.19996 (17)	0.0269 (4)
C5'	1.0252 (2)	0.3441 (2)	0.21214 (19)	0.0323 (5)
H5'A	0.978 (2)	0.4014 (19)	0.1419 (19)	0.038 (6)*
C1"	1.2582 (2)	0.19321 (17)	0.59576 (16)	0.0225 (4)
C2"	1.4054 (2)	0.18783 (18)	0.61535 (17)	0.0269 (4)
C3"	1.4348 (2)	0.2834 (2)	0.64244 (19)	0.0343 (5)
H3"A	1.5348	0.2787	0.6557	0.041*
C4"	1.3191 (2)	0.3854 (2)	0.65021 (19)	0.0377 (5)
H4"A	1.3395	0.4508	0.6691	0.045*
C5"	1.1733 (2)	0.39299 (19)	0.63066 (19)	0.0340 (5)
H5"B	1.0934	0.4632	0.6364	0.041*
C6"	1.1452 (2)	0.29743 (18)	0.60272 (17)	0.0279 (4)
H6"B	1.0457	0.3036	0.5880	0.034*
C1"'	1.3194 (2)	0.33737 (18)	0.07721 (17)	0.0281 (4)
C2"'	1.3156 (2)	0.46021 (19)	−0.02275 (18)	0.0302 (4)
H2"A	1.2259	0.5220	−0.0102	0.036*
C3"'	1.4398 (2)	0.49490 (19)	−0.14068 (18)	0.0302 (4)
C4"'	1.5709 (2)	0.4037 (2)	−0.15924 (18)	0.0344 (5)
C5"'	1.5742 (2)	0.2811 (2)	−0.0599 (2)	0.0373 (5)
H5"A	1.6627	0.2185	−0.0729	0.045*
C6"'	1.4513 (2)	0.2479 (2)	0.05782 (19)	0.0328 (4)
H6"A	1.4574	0.1640	0.1250	0.039*
C7"'	1.4332 (2)	0.6297 (2)	−0.24574 (19)	0.0391 (5)
H7"A	1.4453	0.6232	−0.3273	0.059*
H7"B	1.5209	0.6757	−0.2586	0.059*
H7"C	1.3290	0.6776	−0.2195	0.059*
C8"'	1.7103 (3)	0.4374 (3)	−0.2845 (2)	0.0517 (6)
H8"A	1.7885	0.3608	−0.2813	0.078*
H8"B	1.7631	0.5082	−0.2948	0.078*
H8"C	1.6693	0.4648	−0.3585	0.078*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1'	0.0226 (2)	0.0352 (3)	0.0351 (3)	−0.00144 (19)	−0.0138 (2)	−0.0086 (2)
O1	0.0179 (6)	0.0403 (8)	0.0414 (8)	−0.0060 (6)	−0.0096 (6)	−0.0117 (7)
O2	0.0196 (7)	0.0435 (9)	0.0628 (10)	0.0015 (6)	−0.0179 (7)	−0.0276 (8)
N1	0.0240 (8)	0.0266 (9)	0.0330 (9)	−0.0030 (7)	−0.0136 (7)	−0.0048 (7)
N3	0.0184 (7)	0.0261 (8)	0.0260 (8)	−0.0044 (6)	−0.0092 (6)	−0.0075 (7)
N3'	0.0237 (8)	0.0263 (9)	0.0269 (8)	−0.0032 (6)	−0.0098 (6)	−0.0093 (7)
C2	0.0155 (8)	0.0281 (10)	0.0239 (9)	−0.0028 (7)	−0.0070 (7)	−0.0079 (8)
C4	0.0218 (9)	0.0265 (10)	0.0327 (10)	−0.0071 (7)	−0.0078 (8)	−0.0119 (8)
C5	0.0313 (11)	0.0460 (13)	0.0359 (11)	−0.0136 (9)	−0.0014 (9)	−0.0181 (10)
C6	0.0516 (15)	0.0622 (17)	0.0307 (11)	−0.0241 (12)	0.0012 (10)	−0.0127 (11)
C7	0.0679 (16)	0.0592 (16)	0.0279 (11)	−0.0244 (13)	−0.0143 (11)	−0.0041 (11)
C8	0.0478 (13)	0.0443 (13)	0.0353 (11)	−0.0119 (10)	−0.0196 (10)	−0.0070 (10)
C9	0.0333 (10)	0.0265 (10)	0.0290 (10)	−0.0107 (8)	−0.0104 (8)	−0.0076 (8)
C10	0.0277 (10)	0.0283 (10)	0.0275 (9)	−0.0111 (8)	−0.0057 (8)	−0.0087 (8)
C2'	0.0240 (9)	0.0213 (9)	0.0300 (9)	−0.0036 (7)	−0.0126 (8)	−0.0089 (8)
C4'	0.0301 (10)	0.0254 (10)	0.0283 (9)	−0.0045 (8)	−0.0132 (8)	−0.0086 (8)
C5'	0.0315 (10)	0.0315 (11)	0.0315 (10)	−0.0041 (8)	−0.0170 (9)	−0.0036 (9)
C1"	0.0197 (8)	0.0242 (10)	0.0215 (8)	−0.0072 (7)	−0.0049 (7)	−0.0054 (7)
C2"	0.0193 (9)	0.0311 (11)	0.0291 (10)	−0.0036 (7)	−0.0069 (7)	−0.0105 (8)
C3"	0.0263 (10)	0.0424 (13)	0.0400 (11)	−0.0104 (9)	−0.0118 (9)	−0.0162 (10)
C4"	0.0395 (12)	0.0395 (13)	0.0428 (12)	−0.0124 (9)	−0.0109 (10)	−0.0204 (10)
C5"	0.0321 (10)	0.0299 (11)	0.0402 (11)	−0.0031 (8)	−0.0085 (9)	−0.0160 (9)
C6"	0.0203 (9)	0.0316 (11)	0.0300 (10)	−0.0050 (8)	−0.0070 (8)	−0.0096 (9)
C1"'	0.0289 (10)	0.0322 (11)	0.0260 (9)	−0.0074 (8)	−0.0115 (8)	−0.0091 (8)
C2"'	0.0298 (10)	0.0310 (11)	0.0321 (10)	−0.0032 (8)	−0.0144 (8)	−0.0102 (9)
C3"'	0.0315 (10)	0.0361 (11)	0.0288 (10)	−0.0108 (8)	−0.0147 (8)	−0.0094 (9)
C4"'	0.0291 (10)	0.0482 (13)	0.0302 (10)	−0.0107 (9)	−0.0092 (8)	−0.0153 (10)
C5"'	0.0289 (10)	0.0457 (13)	0.0405 (11)	0.0006 (9)	−0.0123 (9)	−0.0202 (10)
C6"'	0.0341 (11)	0.0322 (11)	0.0331 (10)	−0.0030 (8)	−0.0145 (9)	−0.0100 (9)
C7"'	0.0414 (12)	0.0401 (13)	0.0326 (11)	−0.0155 (10)	−0.0133 (9)	−0.0040 (10)
C8"'	0.0391 (13)	0.0687 (17)	0.0426 (13)	−0.0117 (11)	−0.0017 (10)	−0.0230 (13)

Geometric parameters (Å, º)

S1'—C5'	1.716 (2)	C9—C10	1.403 (2)
S1'—C2'	1.7308 (17)	C4'—C5'	1.355 (2)
O1—C4	1.237 (2)	C4'—C1"'	1.483 (2)
O2—C2"	1.371 (2)	C1"—C6"	1.382 (2)
N1—C9	1.379 (2)	C1"—C2"	1.404 (2)
N1—C2	1.448 (2)	C2"—C3"	1.382 (3)
N3—C4	1.381 (2)	C3"—C4"	1.377 (3)
N3—C2'	1.405 (2)	C4"—C5"	1.384 (3)
N3—C2	1.485 (2)	C5"—C6"	1.383 (3)
N3'—C2'	1.303 (2)	C1"'—C6"'	1.389 (3)
N3'—C4'	1.387 (2)	C1"'—C2"'	1.395 (2)
C2—C1"	1.527 (2)	C2"'—C3"'	1.396 (3)
C4—C10	1.461 (3)	C3"'—C4"'	1.395 (3)
C5—C6	1.368 (3)	C3"'—C7"'	1.510 (3)
C5—C10	1.400 (2)	C4"'—C5"'	1.390 (3)
C6—C7	1.386 (3)	C4"'—C8"'	1.515 (3)
C7—C8	1.381 (3)	C5"'—C6"'	1.388 (3)
C8—C9	1.395 (3)
C5'—S1'—C2'	87.98 (9)	C5'—C4'—C1"'	126.13 (16)
C9—N1—C2	117.71 (15)	N3'—C4'—C1"'	119.55 (15)
C4—N3—C2'	121.23 (14)	C4'—C5'—S1'	111.67 (14)
C4—N3—C2	120.36 (14)	C6"—C1"—C2"	118.03 (17)
C2'—N3—C2	116.62 (13)	C6"—C1"—C2	124.06 (15)
C2'—N3'—C4'	110.18 (15)	C2"—C1"—C2	117.91 (15)
N1—C2—N3	107.49 (13)	O2—C2"—C3"	122.88 (16)
N1—C2—C1"	113.02 (14)	O2—C2"—C1"	116.43 (17)
N3—C2—C1"	111.13 (14)	C3"—C2"—C1"	120.68 (17)
O1—C4—N3	120.11 (16)	C4"—C3"—C2"	120.00 (17)
O1—C4—C10	123.45 (16)	C3"—C4"—C5"	120.33 (19)
N3—C4—C10	116.41 (15)	C6"—C5"—C4"	119.37 (18)
C6—C5—C10	120.9 (2)	C1"—C6"—C5"	121.58 (17)
C5—C6—C7	119.2 (2)	C6"'—C1"'—C2"'	118.53 (17)
C8—C7—C6	121.4 (2)	C6"'—C1"'—C4'	120.55 (16)
C7—C8—C9	119.7 (2)	C2"'—C1"'—C4'	120.89 (17)
N1—C9—C8	122.68 (18)	C1"'—C2"'—C3"'	121.90 (18)
N1—C9—C10	118.06 (16)	C4"'—C3"'—C2"'	118.97 (17)
C8—C9—C10	119.14 (18)	C4"'—C3"'—C7"'	120.61 (17)
C5—C10—C9	119.62 (17)	C2"'—C3"'—C7"'	120.42 (18)
C5—C10—C4	120.20 (17)	C5"'—C4"'—C3"'	119.12 (17)
C9—C10—C4	120.03 (16)	C5"'—C4"'—C8"'	119.86 (19)
N3'—C2'—N3	121.08 (15)	C3"'—C4"'—C8"'	121.01 (19)
N3'—C2'—S1'	115.87 (13)	C6"'—C5"'—C4"'	121.61 (19)
N3—C2'—S1'	122.98 (13)	C5"'—C6"'—C1"'	119.87 (18)
C5'—C4'—N3'	114.29 (16)
C9—N1—C2—N3	−51.2 (2)	C2'—N3'—C4'—C1"'	−177.56 (16)
C9—N1—C2—C1"	71.8 (2)	N3'—C4'—C5'—S1'	−1.2 (2)
C4—N3—C2—N1	42.2 (2)	C1"'—C4'—C5'—S1'	176.78 (15)
C2'—N3—C2—N1	−152.78 (15)	C2'—S1'—C5'—C4'	1.12 (16)
C4—N3—C2—C1"	−81.93 (19)	N1—C2—C1"—C6"	−116.39 (18)
C2'—N3—C2—C1"	83.06 (18)	N3—C2—C1"—C6"	4.6 (2)
C2'—N3—C4—O1	3.6 (3)	N1—C2—C1"—C2"	63.7 (2)
C2—N3—C4—O1	167.90 (16)	N3—C2—C1"—C2"	−175.37 (14)
C2'—N3—C4—C10	−177.93 (16)	C6"—C1"—C2"—O2	179.69 (16)
C2—N3—C4—C10	−13.6 (2)	C2—C1"—C2"—O2	−0.4 (2)
C10—C5—C6—C7	−1.0 (4)	C6"—C1"—C2"—C3"	0.8 (3)
C5—C6—C7—C8	0.7 (4)	C2—C1"—C2"—C3"	−179.23 (16)
C6—C7—C8—C9	0.4 (4)	O2—C2"—C3"—C4"	−178.91 (17)
C2—N1—C9—C8	−152.23 (18)	C1"—C2"—C3"—C4"	−0.1 (3)
C2—N1—C9—C10	31.8 (2)	C2"—C3"—C4"—C5"	−0.2 (3)
C7—C8—C9—N1	−177.0 (2)	C3"—C4"—C5"—C6"	−0.3 (3)
C7—C8—C9—C10	−1.1 (3)	C2"—C1"—C6"—C5"	−1.3 (3)
C6—C5—C10—C9	0.3 (3)	C2—C1"—C6"—C5"	178.78 (17)
C6—C5—C10—C4	175.9 (2)	C4"—C5"—C6"—C1"	1.0 (3)
N1—C9—C10—C5	176.88 (18)	C5'—C4'—C1"'—C6"'	−145.9 (2)
C8—C9—C10—C5	0.7 (3)	N3'—C4'—C1"'—C6"'	32.0 (3)
N1—C9—C10—C4	1.3 (3)	C5'—C4'—C1"'—C2"'	32.2 (3)
C8—C9—C10—C4	−174.83 (18)	N3'—C4'—C1"'—C2"'	−149.92 (17)
O1—C4—C10—C5	−7.2 (3)	C6"'—C1"'—C2"'—C3"'	0.1 (3)
N3—C4—C10—C5	174.40 (17)	C4'—C1"'—C2"'—C3"'	−177.95 (16)
O1—C4—C10—C9	168.34 (18)	C1"'—C2"'—C3"'—C4"'	0.4 (3)
N3—C4—C10—C9	−10.1 (3)	C1"'—C2"'—C3"'—C7"'	−178.81 (17)
C4'—N3'—C2'—N3	−176.67 (16)	C2"'—C3"'—C4"'—C5"'	0.0 (3)
C4'—N3'—C2'—S1'	0.3 (2)	C7"'—C3"'—C4"'—C5"'	179.19 (17)
C4—N3—C2'—N3'	−177.08 (16)	C2"'—C3"'—C4"'—C8"'	−178.90 (18)
C2—N3—C2'—N3'	18.1 (2)	C7"'—C3"'—C4"'—C8"'	0.3 (3)
C4—N3—C2'—S1'	6.1 (2)	C3"'—C4"'—C5"'—C6"'	−0.9 (3)
C2—N3—C2'—S1'	−158.71 (13)	C8"'—C4"'—C5"'—C6"'	178.01 (18)
C5'—S1'—C2'—N3'	−0.85 (15)	C4"'—C5"'—C6"'—C1"'	1.4 (3)
C5'—S1'—C2'—N3	176.09 (16)	C2"'—C1"'—C6"'—C5"'	−1.0 (3)
C2'—N3'—C4'—C5'	0.6 (2)	C4'—C1"'—C6"'—C5"'	177.07 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2"B···O1^i	0.84 (3)	1.93 (3)	2.7682 (18)	173 (3)
N1—H1A···O2	0.80 (2)	2.42 (2)	2.885 (2)	118.4 (18)

Symmetry code: (i) x+1, y, z.