Two N-ortho-nitro­benzene­sulfonyl α,α-disubstituted amino acid adducts

The carboxy group of 2-methyl-N-[(2-nitrophenyl)sulfonyl]­alanine, C₁₀H₁₂N₂O₆S, forms centrosymmetric hydrogen-bonded dimers with an O...O distance of 2.629 (2) Å and an intramolecular N—H...O(nitro) hydrogen bond N...O distance of 2.823 (2) Å. 1-[(2-Nitro­phenyl)­sulfonyl­amino]­cyclo­hexane­carboxyl­ic acid, C₁₃H₁₆N₂O₆S, has Z′ = 2 and forms similar interactions.

S1. Comment

The incorporation of α,α-disubstituted amino acids into short peptide segments can dramatically increase the helical propensity of sequences as short as ten residues (Prasad & Balaram, 1984; Marshall, et al., 1990). This effect has been of recent interest in the development of novel amphipathic helical peptides, designed to exhibit anti-microbial activity under physiological conditions (Wysong et al., 1997; Yokum et al., 1996). However, the incorporation of some α,α-disubstituted amino acids into peptide sequences has proven to be difficult during solid phase peptide synthesis (SPPS) by the use of the Fmoc-acid fluoride (Fmoc = 9-fluorenylmethoxycarbonyl) conditions set forth by Wenschuh et al. (1994). As part of an effort to increase the overall efficacy of the couplings, we have probed the utilization of the acid chloride analogues of several commonly used α,α-disubstituted amino acids, two of which are described here, Aib (2-aminoisobutyric acid) and Cyh (1-amino-1-cyclohexanecarboxylic acid). Because the use of acid chlorides greatly increases the propensity of oxazolone formation under SPPS conditions (Carpino et al., 1991), we experimented with the use of the ortho-nitrobenzensulfonyl protecting group as an alternative to the Fmoc protecting group. The ortho-nitrobenzenesulfonyl group is readily cleaved by nucleophilic displacement (Fukuyama et al., 1995). It is, however, stable under acidic conditions, and is thus orthogonal to the Boc chemistry (Boc = t-butyloxycarbonyl) required for sidegroup protection of several amino acids during SPPS. In addition, due to the lower nucleophilicity of the sulfonyl group, oxazolone formation by intramolecular cyclization is minimized (Miller & Scanlan, 1998). The incorporation of the ortho-nitrobenzenesulfonyl group has the added advantage of introducing a greater propensity towards crystallization of the amino acid derivatives. We herein report the first crystallographic data on the o-nitrobenzenesulfonyl derivatives of these α,α-disubstituted amino acids, oNBS-Aib, (I), and oNBS-Cyh, (II). \sch

oNBS-Aib has Z' = 1, while compound oNBS-Cyh has Z' = 2. The conformations of the molecules are described by five torsion angles: that about the C—NO₂ bond, and the four in the C—S—N—C—C(carboxy) chain. The conformations of oNBS-Aib and the two independent molecules of oNBS-Cyh are quite similar. In all three cases, the NO₂ group is rotated out of the plane of its attached phenyl group by 38.5 (2)–47.1 (3)°, as measured by the magnitudes of torsion angles O5—N2—C8—C3. This is similar to, but slightly smaller than the 52.4 (6)° seen in N,N-dimethyl-o-nitrobenzenesulfonamide (Ruostesuo et al., 1989). The four torsion angles about the C—S—N—C—C(carboxy) chain exhibit good agreement between the two molecules of oNBS-Cyh (mean difference 4.6°), and between oNBS-Aib and oNBS-Cyh (mean differences 4.3° with the unprimed molecule and 6.1° with the primed molecule). This conformation is different, however, from the conformation seen in N-p-toluenesulfonyl-α-aminoisobutyric acid (Crisma et al., 1999), which differs from oNBS-Aib only by having a p-tosyl subsituent on S rather than o-nitrophenyl. In that p-tosyl compound, torsion angles along the C—S—N—C—C(carboxy) chain are, respectively, 52.5 (2), 84.1 (3), 80.1 (3), and 33.7 (4)°. While the N—C—C—O torsion angle of the p-tosyl compound agrees well with those seen in oNBS-Aib and oNBS-Cyh, the other three torsion angles differ by 20–30°.

The likely cause of this conformational difference is hydrogen bonding by the N—H group. In the p-tosyl compound (Crisma et al., 1999), the N—H group forms a near-linear intermolecular hydrogen bond of N···O length 2.893 (3) Å to sulfonyl oxygen. In both oNBS-Aib and oNBS-Cyh, all N—H groups form nonlinear intramolecular contacts to nitro oxygen atoms, and longer, more linear intermolecular interactions with nitro or carboxy O. The COOH group of oNBS-Aib forms a centrosymmetric hydrogen-bonded dimer with O···O distance 2.629 (2) Å. The two independent molecules of oNBS-Cyh form a hydrogen-bonded dimer about a pseudocenter near 1/4, 3/4, 1/2, with O···O distances 2.619 (2) and 2.705 (2) Å.

The difference in the environments of the primed and unprimed molecules may be seen in the hydrogen bonding by the N—H group. That of the primed molecule forms a near-linear intermolecular contact to nitro oxygen O5ⁱ (i = x, 3/2 − y, 1/2 + z, see Table 2), while the nearest distance to the unprimed N—H group is somewhat longer, 3.767 (2) Å to sulfonyl oxygen O1' at x, 3/2 − y, z − 1/2, and somewhat less linear, with N—H···O angle 152 (2)°.

The cyclohexyl group of oNBS-Cyh is in the chair conformation, having endocyclic torsion angle magnitudes in the range 53.9 (2)–57.3 (2)°, in good agreement with the mean value of 54.6° observed in 1-aminocyclohexane-1-carboxylic acid and six of its derivatives (Valle et al., 1988).

We have isolated a second polymorph of oNBS-Cyh having Z' = 1 from the same crystallization, but have not obtained crystals of sufficient quality to report the full structure here. That polymorph has space group P1, with cell dimensions a = 8.48 (2), b = 8.52 (2), c = 11.44 (3) Å, α = 97.2 (2), β = 102.8 (2), γ = 106.1 (2)°, V = 759 (3) ų at 297 K, R = 0.090. Its conformation is quite similar to that of the Z' = 2 polymorph described here.

S2. Experimental

Compounds (1) and (2) were prepared by reacting the corresponding amino acid (1 eq.) with chlorotrimethylsilane (1.85 eq), diisopropylethylamine, (2.3 eq) and ortho-nitrobenzenesulfonyl chloride (0.9 eq) in anhydrous dichloromethane over 12 h (273 K to reflux), followed by aqueous work-up and extraction. Both amino acid derivatives were crystallized by dissolving the crude material in a hot ethanol solution, followed by slow cooling to room temperature.

S3. Refinement

Carboxy and N—H H atoms were located in difference maps and refined individually. Other H atoms were placed in calculated positions with C—H bond distances 0.95 for phenyl and 0.98 Å for methyl, and thereafter treated as riding. A torsional parameter was refined for each methyl group. U_iso = 1.2U_eq of the attached C (1.5 for methyl).

Computing details

For both compounds, data collection: CAD-4 EXPRESS (Enraf Nonius, 1994); cell refinement: CAD-4 EXPRESS. Data reduction: XCAD4 (Harms & Wocadlo, 1995) for (I); maXus (Mackay et al., 1999) for (II). Program(s) used to solve structure: SHELXS97 (Sheldrick, 199b) for (I); SIR92 (Altomare et al., 1993) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997). Software used to prepare material for publication: WinGX publication routines (Farrugia, 1999) for (I); SHELXL97 (Sheldrick, 1997) for (II).

Figures

	Fig. 1. The molecular structure of oNBS-Aib with 50% ellipsoids.
	Fig. 2. The two independent molecules of oNBS-Cyh with 50% ellipsoids.

(I) N-(2-nitrobenzenesulfonyl)-2-amino isobutyric acid

Crystal data

C10H12N2O6S	F(000) = 600
Mr = 288.28	Dx = 1.572 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.665 (3) Å	Cell parameters from 25 reflections
b = 10.614 (2) Å	θ = 14.8–21.1°
c = 11.121 (4) Å	µ = 0.29 mm^−1
β = 117.80 (2)°	T = 100 K
V = 1217.9 (6) Å^3	Prism, colorless
Z = 4	0.45 × 0.43 × 0.20 mm

Data collection

Enraf-Nonius CAD4 (with Oxford Cryostream) diffractometer	Rint = 0.035
ω–2θ scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: ψ scan (North et al., 1968)	h = −16→14
Tmin = 0.880, Tmax = 0.944	k = −14→8
4282 measured reflections	l = 0→15
3536 independent reflections	3 standard reflections every 60 min
2710 reflections with I > 2σ(I)	intensity decay: 5.0%

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0437P)^2 + 0.4249P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.042	(Δ/σ)max = 0.001
wR(F^2) = 0.109	Δρmax = 0.46 e Å^−3
S = 1.03	Δρmin = −0.37 e Å^−3
3536 reflections	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
183 parameters	Extinction coefficient: 0.0105 (14)
0 restraints

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.

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

	x	y	z	Uiso*/Ueq
S	0.72056 (4)	0.74709 (4)	0.66517 (4)	0.01288 (11)
O1	0.73513 (12)	0.63104 (13)	0.73690 (13)	0.0188 (3)
O2	0.69106 (12)	0.86147 (12)	0.71433 (13)	0.0189 (3)
O3	0.98574 (12)	0.85716 (12)	0.91026 (12)	0.0152 (3)
O4	0.94016 (12)	1.05851 (11)	0.84208 (12)	0.0149 (3)
O5	0.78235 (12)	0.53798 (12)	0.52256 (14)	0.0204 (3)
O6	0.62615 (13)	0.40202 (12)	0.44478 (14)	0.0227 (3)
N1	0.84935 (14)	0.77553 (14)	0.65117 (15)	0.0147 (3)
N2	0.66683 (14)	0.50992 (14)	0.46771 (15)	0.0146 (3)
C1	0.94529 (15)	0.94668 (16)	0.81806 (16)	0.0121 (3)
C2	0.91241 (16)	0.89947 (16)	0.67511 (16)	0.0131 (3)
C3	0.59119 (16)	0.72314 (16)	0.49805 (16)	0.0129 (3)
C4	0.49572 (17)	0.81608 (17)	0.44523 (18)	0.0165 (3)
H4	0.5051	0.8910	0.4956	0.020*
C5	0.38713 (17)	0.80018 (19)	0.31969 (19)	0.0200 (4)
H5	0.3241	0.8652	0.2840	0.024*
C6	0.37020 (17)	0.69041 (19)	0.24650 (18)	0.0198 (4)
H6	0.296	0.6804	0.1605	0.024*
C7	0.46168 (16)	0.59461 (18)	0.29862 (17)	0.0168 (4)
H7	0.4492	0.5178	0.2502	0.020*
C8	0.57152 (16)	0.61270 (16)	0.42241 (17)	0.0134 (3)
C9	1.04188 (17)	0.87881 (18)	0.6737 (2)	0.0189 (4)
H9A	1.0929	0.8158	0.7424	0.028*
H9B	1.0899	0.9584	0.6942	0.028*
H9C	1.0256	0.8490	0.5837	0.028*
C10	0.82947 (18)	0.99529 (18)	0.56642 (18)	0.0191 (4)
H10A	0.8111	0.9634	0.4765	0.029*
H10B	0.8763	1.0754	0.5835	0.029*
H10C	0.7478	1.0085	0.5696	0.029*
H3O	1.010 (3)	0.894 (3)	0.991 (3)	0.053 (9)*
H1N	0.887 (2)	0.716 (2)	0.648 (3)	0.034 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S	0.01306 (19)	0.0156 (2)	0.01038 (19)	−0.00238 (15)	0.00576 (15)	−0.00250 (15)
O1	0.0188 (6)	0.0226 (7)	0.0142 (6)	−0.0027 (5)	0.0071 (5)	0.0032 (5)
O2	0.0184 (6)	0.0227 (7)	0.0172 (6)	−0.0025 (5)	0.0097 (5)	−0.0081 (5)
O3	0.0194 (6)	0.0140 (6)	0.0105 (6)	−0.0020 (5)	0.0055 (5)	−0.0017 (5)
O4	0.0181 (6)	0.0134 (6)	0.0116 (6)	0.0001 (5)	0.0054 (5)	−0.0013 (5)
O5	0.0135 (6)	0.0189 (6)	0.0243 (7)	0.0004 (5)	0.0050 (5)	−0.0030 (5)
O6	0.0277 (7)	0.0129 (6)	0.0289 (7)	−0.0044 (5)	0.0145 (6)	−0.0041 (5)
N1	0.0144 (7)	0.0138 (7)	0.0174 (7)	−0.0035 (5)	0.0085 (6)	−0.0057 (6)
N2	0.0173 (7)	0.0150 (7)	0.0130 (7)	−0.0008 (5)	0.0084 (6)	−0.0026 (5)
C1	0.0105 (7)	0.0145 (8)	0.0107 (7)	−0.0017 (6)	0.0045 (6)	−0.0008 (6)
C2	0.0150 (7)	0.0140 (8)	0.0097 (7)	−0.0030 (6)	0.0053 (6)	−0.0023 (6)
C3	0.0119 (7)	0.0151 (8)	0.0108 (7)	−0.0020 (6)	0.0044 (6)	−0.0006 (6)
C4	0.0170 (8)	0.0154 (8)	0.0177 (8)	−0.0005 (6)	0.0086 (7)	−0.0006 (7)
C5	0.0153 (8)	0.0228 (9)	0.0198 (9)	0.0042 (7)	0.0065 (7)	0.0039 (7)
C6	0.0137 (8)	0.0299 (10)	0.0125 (8)	−0.0019 (7)	0.0034 (6)	−0.0007 (7)
C7	0.0159 (8)	0.0213 (9)	0.0136 (8)	−0.0043 (6)	0.0072 (7)	−0.0041 (7)
C8	0.0138 (7)	0.0131 (7)	0.0143 (7)	−0.0014 (6)	0.0074 (6)	−0.0003 (6)
C9	0.0186 (8)	0.0201 (9)	0.0217 (9)	−0.0042 (7)	0.0126 (7)	−0.0057 (7)
C10	0.0257 (9)	0.0186 (9)	0.0115 (8)	−0.0004 (7)	0.0075 (7)	−0.0002 (7)

Geometric parameters (Å, º)

S—O1	1.4338 (13)	C3—C8	1.398 (2)
S—O2	1.4376 (13)	C4—C5	1.390 (3)
S—N1	1.6096 (16)	C4—H4	0.95
S—C3	1.7832 (18)	C5—C6	1.382 (3)
O3—C1	1.314 (2)	C5—H5	0.95
O3—H3O	0.90 (3)	C6—C7	1.390 (3)
O4—C1	1.224 (2)	C6—H6	0.95
O5—N2	1.2287 (18)	C7—C8	1.389 (2)
O6—N2	1.2203 (19)	C7—H7	0.95
N1—C2	1.470 (2)	C9—H9A	0.98
N1—H1N	0.78 (3)	C9—H9B	0.98
N2—C8	1.469 (2)	C9—H9C	0.98
C1—C2	1.535 (2)	C10—H10A	0.98
C2—C10	1.530 (2)	C10—H10B	0.98
C2—C9	1.533 (2)	C10—H10C	0.98
C3—C4	1.396 (2)
O1—S—O2	120.08 (8)	C5—C4—H4	119.6
O1—S—N1	109.95 (8)	C3—C4—H4	119.6
O2—S—N1	106.15 (8)	C6—C5—C4	120.46 (17)
O1—S—C3	106.29 (8)	C6—C5—H5	119.8
O2—S—C3	106.28 (8)	C4—C5—H5	119.8
N1—S—C3	107.47 (8)	C5—C6—C7	120.02 (16)
C1—O3—H3O	107.2 (19)	C5—C6—H6	120
C2—N1—S	124.14 (12)	C7—C6—H6	120
C2—N1—H1N	119.4 (19)	C8—C7—C6	119.09 (17)
S—N1—H1N	115.0 (19)	C8—C7—H7	120.5
O6—N2—O5	124.11 (15)	C6—C7—H7	120.5
O6—N2—C8	117.84 (14)	C7—C8—C3	121.94 (16)
O5—N2—C8	118.01 (14)	C7—C8—N2	115.99 (15)
O4—C1—O3	124.56 (16)	C3—C8—N2	122.06 (15)
O4—C1—C2	121.90 (15)	C2—C9—H9A	109.5
O3—C1—C2	113.42 (14)	C2—C9—H9B	109.5
N1—C2—C10	111.92 (14)	H9A—C9—H9B	109.5
N1—C2—C9	106.39 (14)	C2—C9—H9C	109.5
C10—C2—C9	110.50 (15)	H9A—C9—H9C	109.5
N1—C2—C1	110.00 (14)	H9B—C9—H9C	109.5
C10—C2—C1	111.20 (14)	C2—C10—H10A	109.5
C9—C2—C1	106.58 (14)	C2—C10—H10B	109.5
C4—C3—C8	117.68 (15)	H10A—C10—H10B	109.5
C4—C3—S	117.33 (13)	C2—C10—H10C	109.5
C8—C3—S	124.63 (13)	H10A—C10—H10C	109.5
C5—C4—C3	120.75 (17)	H10B—C10—H10C	109.5
O1—S—N1—C2	−135.75 (14)	N1—S—C3—C8	77.28 (16)
O2—S—N1—C2	−4.43 (16)	C8—C3—C4—C5	−2.0 (3)
C3—S—N1—C2	108.97 (15)	S—C3—C4—C5	−175.44 (14)
S—N1—C2—C10	−68.35 (19)	C3—C4—C5—C6	1.7 (3)
S—N1—C2—C9	170.86 (12)	C4—C5—C6—C7	0.4 (3)
S—N1—C2—C1	55.80 (19)	C5—C6—C7—C8	−2.1 (3)
O4—C1—C2—N1	−145.24 (16)	C6—C7—C8—C3	1.8 (3)
O3—C1—C2—N1	38.50 (19)	C6—C7—C8—N2	−177.08 (16)
O4—C1—C2—C10	−20.7 (2)	C4—C3—C8—C7	0.2 (2)
O3—C1—C2—C10	163.06 (14)	S—C3—C8—C7	173.18 (14)
O4—C1—C2—C9	99.81 (18)	C4—C3—C8—N2	179.02 (15)
O3—C1—C2—C9	−76.45 (17)	S—C3—C8—N2	−8.0 (2)
O1—S—C3—C4	132.56 (14)	O6—N2—C8—C7	−37.5 (2)
O2—S—C3—C4	3.56 (16)	O5—N2—C8—C7	140.35 (16)
N1—S—C3—C4	−109.76 (14)	O6—N2—C8—C3	143.65 (17)
O1—S—C3—C8	−40.41 (16)	O5—N2—C8—C3	−38.5 (2)
O2—S—C3—C8	−169.41 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4^i	0.90 (3)	1.74 (3)	2.629 (2)	171 (3)
N1—H1N···O5	0.78 (3)	2.32 (3)	2.823 (2)	123 (2)
N1—H1N···O4^ii	0.78 (3)	2.58 (3)	3.342 (2)	165 (2)

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

(II) N-(2-nitrobenzenesulfonyl)-1-amino-1-cyclohexane carboxylic acid

Crystal data

C13H16N2O6S	F(000) = 1376
Mr = 328.34	Dx = 1.479 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.9780 (12) Å	Cell parameters from 25 reflections
b = 14.9840 (11) Å	θ = 10.6–21.2°
c = 13.436 (1) Å	µ = 0.25 mm^−1
β = 113.568 (6)°	T = 100 K
V = 2948.4 (4) Å^3	Fragment, colorless
Z = 8	0.55 × 0.42 × 0.35 mm

Data collection

Enraf-Nonius CAD4 (with Oxford Cryostream) diffractometer	5772 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 29.0°, θmin = 2.1°
ω–2θ scans	h = 0→21
Absorption correction: ψ scan (North et al., 1968)	k = −20→20
Tmin = 0.887, Tmax = 0.916	l = −18→16
9183 measured reflections	3 standard reflections every 60 min
7815 independent reflections	intensity decay: 2.7%

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 = 1.09	w = 1/[σ^2(Fo^2) + (0.0311P)^2 + 2.1884P] where P = (Fo^2 + 2Fc^2)/3
7815 reflections	(Δ/σ)max = 0.001
413 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.61 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.

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

	x	y	z	Uiso*/Ueq
S1	0.09596 (3)	0.97588 (3)	0.32063 (4)	0.01886 (11)
O1	0.07698 (10)	0.95375 (10)	0.21026 (12)	0.0263 (3)
O2	0.06725 (10)	0.91675 (10)	0.38543 (13)	0.0253 (3)
O3	0.24607 (11)	0.81592 (10)	0.40654 (12)	0.0231 (3)
H3O	0.241 (2)	0.760 (2)	0.413 (2)	0.055 (10)*
O4	0.24094 (10)	0.81240 (9)	0.57073 (11)	0.0214 (3)
O5	0.14870 (10)	1.12141 (11)	0.19518 (12)	0.0257 (3)
O6	0.01772 (13)	1.15342 (15)	0.06488 (13)	0.0448 (5)
N1	0.20410 (11)	0.99212 (11)	0.38608 (14)	0.0177 (3)
H1N	0.2302 (18)	1.0027 (18)	0.345 (2)	0.032 (7)*
N2	0.06654 (12)	1.13870 (12)	0.15986 (14)	0.0241 (4)
C1	0.24585 (12)	0.85404 (13)	0.49489 (16)	0.0173 (4)
C2	0.25654 (13)	0.95561 (13)	0.49575 (15)	0.0170 (4)
C3	0.04003 (12)	1.07902 (13)	0.31794 (16)	0.0172 (4)
C4	0.00172 (14)	1.09270 (15)	0.39323 (18)	0.0245 (4)
H4	0.0113	1.0496	0.4486	0.029*
C5	−0.05019 (14)	1.16799 (15)	0.38932 (18)	0.0259 (4)
H5	−0.0745	1.1767	0.4426	0.031*
C6	−0.06639 (13)	1.23023 (14)	0.30794 (17)	0.0210 (4)
H6	−0.1031	1.2811	0.3041	0.025*
C7	−0.02901 (13)	1.21842 (13)	0.23183 (16)	0.0203 (4)
H7	−0.0401	1.2609	0.1755	0.024*
C8	0.02452 (13)	1.14433 (13)	0.23865 (15)	0.0166 (4)
C9	0.35848 (13)	0.97477 (14)	0.52258 (17)	0.0215 (4)
H9A	0.3966	0.9447	0.5915	0.026*
H9B	0.3747	0.9498	0.4645	0.026*
C10	0.22940 (14)	0.99947 (13)	0.58202 (17)	0.0215 (4)
H10A	0.1636	0.9894	0.5631	0.026*
H10B	0.2640	0.9714	0.6535	0.026*
C11	0.37919 (14)	1.07499 (14)	0.53325 (18)	0.0256 (4)
H11A	0.4456	1.0841	0.5559	0.031*
H11B	0.3475	1.1038	0.4616	0.031*
C12	0.34900 (16)	1.11890 (16)	0.61550 (18)	0.0302 (5)
H12A	0.3584	1.1842	0.6152	0.036*
H12B	0.3870	1.0963	0.6891	0.036*
C13	0.24882 (15)	1.09985 (14)	0.58985 (18)	0.0259 (4)
H13A	0.2104	1.1287	0.5202	0.031*
H13B	0.2325	1.1259	0.6474	0.031*
S1'	0.39312 (3)	0.48665 (3)	0.68607 (4)	0.01874 (11)
O1'	0.39760 (11)	0.49706 (10)	0.79381 (12)	0.0277 (3)
O2'	0.42115 (10)	0.55820 (10)	0.63517 (13)	0.0258 (3)
O3'	0.23298 (11)	0.63264 (10)	0.58293 (12)	0.0233 (3)
H3O'	0.231 (2)	0.691 (2)	0.573 (2)	0.054 (9)*
O4'	0.23567 (10)	0.64204 (9)	0.41800 (11)	0.0223 (3)
O5'	0.34019 (10)	0.31660 (11)	0.77393 (12)	0.0268 (3)
O6'	0.46285 (12)	0.27744 (12)	0.91166 (13)	0.0334 (4)
N1'	0.29094 (11)	0.46090 (11)	0.60551 (13)	0.0172 (3)
H1N'	0.2599 (18)	0.4333 (18)	0.632 (2)	0.033 (7)*
N2'	0.42296 (12)	0.30432 (11)	0.81867 (14)	0.0224 (4)
C1'	0.23842 (12)	0.59795 (13)	0.49588 (16)	0.0176 (4)
C2'	0.24470 (13)	0.49593 (12)	0.49482 (15)	0.0161 (4)
C3'	0.46525 (13)	0.39516 (13)	0.68908 (16)	0.0189 (4)
C4'	0.51743 (13)	0.40143 (15)	0.62783 (18)	0.0248 (4)
H4'	0.5119	0.4528	0.5841	0.030*
C5'	0.57751 (15)	0.33409 (16)	0.6293 (2)	0.0302 (5)
H5'	0.6109	0.3387	0.5849	0.036*
C6'	0.58903 (14)	0.25994 (15)	0.69563 (19)	0.0277 (5)
H6'	0.6304	0.2140	0.6968	0.033*
C7'	0.53985 (14)	0.25345 (14)	0.75990 (18)	0.0243 (4)
H7'	0.5486	0.2040	0.8072	0.029*
C8'	0.47783 (13)	0.31967 (13)	0.75465 (16)	0.0182 (4)
C9'	0.14586 (13)	0.45971 (14)	0.45016 (16)	0.0201 (4)
H9'1	0.1178	0.4742	0.5019	0.024*
H9'2	0.1096	0.4896	0.3804	0.024*
C10'	0.29091 (14)	0.46655 (13)	0.41918 (16)	0.0197 (4)
H10C	0.2601	0.4960	0.3478	0.024*
H10D	0.3554	0.4864	0.4503	0.024*
C11'	0.14241 (14)	0.35880 (14)	0.43242 (18)	0.0241 (4)
H11C	0.1723	0.3285	0.5035	0.029*
H11D	0.0779	0.3392	0.3997	0.029*
C12'	0.18975 (15)	0.33127 (15)	0.35862 (18)	0.0263 (5)
H12C	0.1898	0.2654	0.3531	0.032*
H12D	0.1557	0.3557	0.2849	0.032*
C13'	0.28770 (14)	0.36558 (14)	0.40289 (18)	0.0230 (4)
H13C	0.3159	0.3502	0.3516	0.028*
H13D	0.3234	0.3361	0.4731	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0155 (2)	0.0109 (2)	0.0234 (2)	−0.00006 (17)	0.00072 (18)	0.00085 (18)
O1	0.0237 (7)	0.0180 (7)	0.0255 (8)	0.0024 (6)	−0.0023 (6)	−0.0046 (6)
O2	0.0182 (7)	0.0142 (7)	0.0367 (9)	−0.0004 (6)	0.0038 (6)	0.0074 (6)
O3	0.0322 (8)	0.0151 (7)	0.0228 (7)	0.0032 (6)	0.0118 (6)	0.0021 (6)
O4	0.0261 (7)	0.0155 (7)	0.0237 (7)	0.0038 (6)	0.0112 (6)	0.0044 (6)
O5	0.0223 (7)	0.0281 (8)	0.0276 (8)	0.0021 (6)	0.0110 (6)	0.0002 (6)
O6	0.0444 (11)	0.0687 (14)	0.0205 (8)	0.0264 (10)	0.0123 (8)	0.0153 (8)
N1	0.0154 (8)	0.0156 (8)	0.0184 (8)	0.0014 (6)	0.0030 (6)	0.0037 (6)
N2	0.0261 (9)	0.0240 (9)	0.0219 (9)	0.0065 (7)	0.0094 (7)	0.0046 (7)
C1	0.0129 (8)	0.0161 (9)	0.0204 (9)	0.0048 (7)	0.0040 (7)	0.0030 (7)
C2	0.0148 (8)	0.0145 (9)	0.0179 (9)	0.0020 (7)	0.0026 (7)	0.0025 (7)
C3	0.0121 (8)	0.0147 (9)	0.0212 (9)	−0.0007 (7)	0.0028 (7)	0.0006 (7)
C4	0.0214 (10)	0.0242 (11)	0.0303 (11)	0.0042 (8)	0.0129 (9)	0.0104 (9)
C5	0.0214 (10)	0.0284 (11)	0.0311 (11)	0.0027 (9)	0.0140 (9)	0.0045 (9)
C6	0.0156 (9)	0.0163 (9)	0.0285 (10)	0.0021 (7)	0.0060 (8)	−0.0001 (8)
C7	0.0194 (9)	0.0148 (9)	0.0232 (10)	0.0017 (7)	0.0050 (8)	0.0044 (7)
C8	0.0156 (8)	0.0149 (9)	0.0175 (9)	−0.0014 (7)	0.0046 (7)	0.0003 (7)
C9	0.0143 (9)	0.0232 (10)	0.0222 (10)	0.0011 (8)	0.0024 (8)	0.0029 (8)
C10	0.0224 (10)	0.0181 (10)	0.0230 (10)	0.0012 (8)	0.0081 (8)	−0.0012 (8)
C11	0.0184 (9)	0.0234 (11)	0.0285 (11)	−0.0057 (8)	0.0027 (8)	0.0026 (9)
C12	0.0316 (12)	0.0230 (11)	0.0275 (11)	−0.0081 (9)	0.0030 (9)	−0.0039 (9)
C13	0.0304 (11)	0.0183 (10)	0.0267 (11)	−0.0017 (9)	0.0090 (9)	−0.0054 (8)
S1'	0.0185 (2)	0.0112 (2)	0.0201 (2)	−0.00045 (17)	0.00089 (18)	−0.00002 (17)
O1'	0.0337 (9)	0.0224 (8)	0.0192 (7)	0.0030 (6)	0.0022 (6)	−0.0057 (6)
O2'	0.0215 (7)	0.0129 (7)	0.0344 (8)	−0.0038 (6)	0.0024 (6)	0.0045 (6)
O3'	0.0348 (8)	0.0144 (7)	0.0238 (7)	0.0040 (6)	0.0149 (7)	0.0011 (6)
O4'	0.0292 (8)	0.0148 (7)	0.0224 (7)	0.0032 (6)	0.0099 (6)	0.0035 (6)
O5'	0.0213 (7)	0.0271 (8)	0.0303 (8)	0.0018 (6)	0.0087 (6)	0.0061 (7)
O6'	0.0386 (9)	0.0337 (9)	0.0248 (8)	0.0096 (8)	0.0096 (7)	0.0139 (7)
N1'	0.0158 (8)	0.0157 (8)	0.0183 (8)	−0.0020 (6)	0.0048 (6)	0.0043 (6)
N2'	0.0273 (9)	0.0158 (8)	0.0223 (8)	0.0018 (7)	0.0080 (7)	0.0047 (7)
C1'	0.0126 (8)	0.0164 (9)	0.0215 (9)	0.0027 (7)	0.0045 (7)	0.0019 (7)
C2'	0.0160 (8)	0.0133 (9)	0.0169 (9)	0.0017 (7)	0.0045 (7)	0.0021 (7)
C3'	0.0129 (8)	0.0156 (9)	0.0217 (9)	−0.0015 (7)	−0.0001 (7)	−0.0006 (7)
C4'	0.0160 (9)	0.0251 (11)	0.0301 (11)	−0.0002 (8)	0.0058 (8)	0.0084 (9)
C5'	0.0202 (10)	0.0342 (13)	0.0378 (13)	0.0025 (9)	0.0134 (9)	0.0037 (10)
C6'	0.0185 (10)	0.0251 (11)	0.0355 (12)	0.0030 (8)	0.0068 (9)	−0.0021 (9)
C7'	0.0205 (10)	0.0167 (9)	0.0285 (11)	0.0011 (8)	0.0022 (8)	0.0013 (8)
C8'	0.0161 (9)	0.0141 (9)	0.0199 (9)	−0.0021 (7)	0.0026 (7)	0.0004 (7)
C9'	0.0137 (8)	0.0213 (10)	0.0224 (10)	0.0002 (7)	0.0041 (7)	0.0006 (8)
C10'	0.0207 (9)	0.0167 (9)	0.0222 (10)	0.0018 (7)	0.0092 (8)	0.0009 (7)
C11'	0.0230 (10)	0.0215 (10)	0.0258 (10)	−0.0072 (8)	0.0076 (8)	−0.0051 (8)
C12'	0.0284 (11)	0.0232 (11)	0.0258 (11)	−0.0045 (9)	0.0093 (9)	−0.0078 (9)
C13'	0.0258 (10)	0.0166 (9)	0.0274 (11)	0.0006 (8)	0.0114 (9)	−0.0033 (8)

Geometric parameters (Å, º)

S1—O1	1.4287 (16)	S1'—O1'	1.4290 (15)
S1—O2	1.4397 (15)	S1'—O2'	1.4363 (15)
S1—N1	1.6134 (17)	S1'—N1'	1.6041 (17)
S1—C3	1.778 (2)	S1'—C3'	1.781 (2)
O3—C1	1.319 (2)	O3'—C1'	1.314 (2)
O3—H3O	0.85 (3)	O3'—H3O'	0.89 (3)
O4—C1	1.224 (2)	O4'—C1'	1.223 (2)
O5—N2	1.232 (2)	O5'—N2'	1.228 (2)
O6—N2	1.221 (2)	O6'—N2'	1.222 (2)
N1—C2	1.478 (2)	N1'—C2'	1.468 (2)
N1—H1N	0.83 (3)	N1'—H1N'	0.83 (3)
N2—C8	1.465 (3)	N2'—C8'	1.471 (3)
C1—C2	1.531 (3)	C1'—C2'	1.532 (3)
C2—C10	1.538 (3)	C2'—C10'	1.540 (3)
C2—C9	1.548 (3)	C2'—C9'	1.546 (3)
C3—C4	1.391 (3)	C3'—C4'	1.389 (3)
C3—C8	1.394 (3)	C3'—C8'	1.398 (3)
C4—C5	1.389 (3)	C4'—C5'	1.387 (3)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.381 (3)	C5'—C6'	1.389 (3)
C5—H5	0.9500	C5'—H5'	0.9500
C6—C7	1.386 (3)	C6'—C7'	1.384 (3)
C6—H6	0.9500	C6'—H6'	0.9500
C7—C8	1.382 (3)	C7'—C8'	1.384 (3)
C7—H7	0.9500	C7'—H7'	0.9500
C9—C11	1.532 (3)	C9'—C11'	1.528 (3)
C9—H9A	0.9900	C9'—H9'1	0.9900
C9—H9B	0.9900	C9'—H9'2	0.9900
C10—C13	1.531 (3)	C10'—C13'	1.527 (3)
C10—H10A	0.9900	C10'—H10C	0.9900
C10—H10B	0.9900	C10'—H10D	0.9900
C11—C12	1.521 (3)	C11'—C12'	1.525 (3)
C11—H11A	0.9900	C11'—H11C	0.9900
C11—H11B	0.9900	C11'—H11D	0.9900
C12—C13	1.524 (3)	C12'—C13'	1.524 (3)
C12—H12A	0.9900	C12'—H12C	0.9900
C12—H12B	0.9900	C12'—H12D	0.9900
C13—H13A	0.9900	C13'—H13C	0.9900
C13—H13B	0.9900	C13'—H13D	0.9900
O1—S1—O2	119.88 (10)	O1'—S1'—O2'	120.14 (10)
O1—S1—N1	109.71 (10)	O1'—S1'—N1'	109.58 (9)
O2—S1—N1	107.09 (9)	O2'—S1'—N1'	106.57 (9)
O1—S1—C3	106.51 (9)	O1'—S1'—C3'	106.93 (9)
O2—S1—C3	105.55 (9)	O2'—S1'—C3'	105.26 (10)
N1—S1—C3	107.46 (9)	N1'—S1'—C3'	107.76 (9)
C1—O3—H3O	108 (2)	C1'—O3'—H3O'	105 (2)
C2—N1—S1	122.97 (14)	C2'—N1'—S1'	124.19 (13)
C2—N1—H1N	120.0 (19)	C2'—N1'—H1N'	117.9 (18)
S1—N1—H1N	112.2 (18)	S1'—N1'—H1N'	117.1 (18)
O6—N2—O5	125.31 (19)	O6'—N2'—O5'	124.70 (18)
O6—N2—C8	117.33 (17)	O6'—N2'—C8'	117.40 (17)
O5—N2—C8	117.34 (17)	O5'—N2'—C8'	117.85 (16)
O4—C1—O3	123.57 (18)	O4'—C1'—O3'	123.72 (18)
O4—C1—C2	123.00 (18)	O4'—C1'—C2'	120.72 (18)
O3—C1—C2	113.38 (17)	O3'—C1'—C2'	115.52 (17)
N1—C2—C1	110.08 (16)	N1'—C2'—C1'	110.83 (16)
N1—C2—C10	112.02 (16)	N1'—C2'—C10'	112.74 (15)
C1—C2—C10	111.48 (16)	C1'—C2'—C10'	109.98 (16)
N1—C2—C9	106.73 (16)	N1'—C2'—C9'	106.85 (15)
C1—C2—C9	106.86 (15)	C1'—C2'—C9'	107.06 (15)
C10—C2—C9	109.44 (16)	C10'—C2'—C9'	109.17 (16)
C4—C3—C8	117.19 (18)	C4'—C3'—C8'	117.32 (18)
C4—C3—S1	118.49 (15)	C4'—C3'—S1'	118.08 (16)
C8—C3—S1	124.05 (15)	C8'—C3'—S1'	124.45 (16)
C5—C4—C3	121.46 (19)	C5'—C4'—C3'	121.2 (2)
C5—C4—H4	119.3	C5'—C4'—H4'	119.4
C3—C4—H4	119.3	C3'—C4'—H4'	119.4
C6—C5—C4	119.9 (2)	C4'—C5'—C6'	120.3 (2)
C6—C5—H5	120.0	C4'—C5'—H5'	119.8
C4—C5—H5	120.0	C6'—C5'—H5'	119.8
C5—C6—C7	119.89 (19)	C7'—C6'—C5'	119.6 (2)
C5—C6—H6	120.1	C7'—C6'—H6'	120.2
C7—C6—H6	120.1	C5'—C6'—H6'	120.2
C8—C7—C6	119.44 (18)	C6'—C7'—C8'	119.4 (2)
C8—C7—H7	120.3	C6'—C7'—H7'	120.3
C6—C7—H7	120.3	C8'—C7'—H7'	120.3
C7—C8—C3	122.05 (18)	C7'—C8'—C3'	122.13 (19)
C7—C8—N2	116.66 (17)	C7'—C8'—N2'	116.10 (17)
C3—C8—N2	121.26 (17)	C3'—C8'—N2'	121.73 (17)
C11—C9—C2	111.80 (17)	C11'—C9'—C2'	112.05 (16)
C11—C9—H9A	109.3	C11'—C9'—H9'1	109.2
C2—C9—H9A	109.3	C2'—C9'—H9'1	109.2
C11—C9—H9B	109.3	C11'—C9'—H9'2	109.2
C2—C9—H9B	109.3	C2'—C9'—H9'2	109.2
H9A—C9—H9B	107.9	H9'1—C9'—H9'2	107.9
C13—C10—C2	111.17 (17)	C13'—C10'—C2'	112.35 (16)
C13—C10—H10A	109.4	C13'—C10'—H10C	109.1
C2—C10—H10A	109.4	C2'—C10'—H10C	109.1
C13—C10—H10B	109.4	C13'—C10'—H10D	109.1
C2—C10—H10B	109.4	C2'—C10'—H10D	109.1
H10A—C10—H10B	108.0	H10C—C10'—H10D	107.9
C12—C11—C9	111.87 (18)	C12'—C11'—C9'	111.88 (18)
C12—C11—H11A	109.2	C12'—C11'—H11C	109.2
C9—C11—H11A	109.2	C9'—C11'—H11C	109.2
C12—C11—H11B	109.2	C12'—C11'—H11D	109.2
C9—C11—H11B	109.2	C9'—C11'—H11D	109.2
H11A—C11—H11B	107.9	H11C—C11'—H11D	107.9
C11—C12—C13	111.37 (18)	C13'—C12'—C11'	110.72 (17)
C11—C12—H12A	109.4	C13'—C12'—H12C	109.5
C13—C12—H12A	109.4	C11'—C12'—H12C	109.5
C11—C12—H12B	109.4	C13'—C12'—H12D	109.5
C13—C12—H12B	109.4	C11'—C12'—H12D	109.5
H12A—C12—H12B	108.0	H12C—C12'—H12D	108.1
C12—C13—C10	111.43 (18)	C12'—C13'—C10'	111.14 (18)
C12—C13—H13A	109.3	C12'—C13'—H13C	109.4
C10—C13—H13A	109.3	C10'—C13'—H13C	109.4
C12—C13—H13B	109.3	C12'—C13'—H13D	109.4
C10—C13—H13B	109.3	C10'—C13'—H13D	109.4
H13A—C13—H13B	108.0	H13C—C13'—H13D	108.0
O1—S1—N1—C2	−135.74 (16)	O1'—S1'—N1'—C2'	140.35 (16)
O2—S1—N1—C2	−4.15 (18)	O2'—S1'—N1'—C2'	8.92 (18)
C3—S1—N1—C2	108.84 (16)	C3'—S1'—N1'—C2'	−103.64 (17)
S1—N1—C2—C1	56.7 (2)	S1'—N1'—C2'—C1'	−59.4 (2)
S1—N1—C2—C10	−67.9 (2)	S1'—N1'—C2'—C10'	64.3 (2)
S1—N1—C2—C9	172.30 (14)	S1'—N1'—C2'—C9'	−175.73 (13)
O4—C1—C2—N1	−143.38 (18)	O4'—C1'—C2'—N1'	152.01 (17)
O3—C1—C2—N1	39.1 (2)	O3'—C1'—C2'—N1'	−30.4 (2)
O4—C1—C2—C10	−18.4 (3)	O4'—C1'—C2'—C10'	26.7 (2)
O3—C1—C2—C10	164.06 (16)	O3'—C1'—C2'—C10'	−155.69 (16)
O4—C1—C2—C9	101.1 (2)	O4'—C1'—C2'—C9'	−91.8 (2)
O3—C1—C2—C9	−76.4 (2)	O3'—C1'—C2'—C9'	85.8 (2)
O1—S1—C3—C4	143.90 (16)	O1'—S1'—C3'—C4'	−141.09 (16)
O2—S1—C3—C4	15.46 (18)	O2'—S1'—C3'—C4'	−12.26 (18)
N1—S1—C3—C4	−98.58 (17)	N1'—S1'—C3'—C4'	101.18 (17)
O1—S1—C3—C8	−29.91 (19)	O1'—S1'—C3'—C8'	34.36 (19)
O2—S1—C3—C8	−158.35 (16)	O2'—S1'—C3'—C8'	163.20 (16)
N1—S1—C3—C8	87.61 (18)	N1'—S1'—C3'—C8'	−83.36 (18)
C8—C3—C4—C5	0.3 (3)	C8'—C3'—C4'—C5'	1.9 (3)
S1—C3—C4—C5	−173.91 (17)	S1'—C3'—C4'—C5'	177.69 (17)
C3—C4—C5—C6	1.5 (3)	C3'—C4'—C5'—C6'	−2.3 (3)
C4—C5—C6—C7	−1.5 (3)	C4'—C5'—C6'—C7'	0.3 (3)
C5—C6—C7—C8	−0.3 (3)	C5'—C6'—C7'—C8'	2.0 (3)
C6—C7—C8—C3	2.1 (3)	C6'—C7'—C8'—C3'	−2.3 (3)
C6—C7—C8—N2	−176.32 (18)	C6'—C7'—C8'—N2'	175.20 (19)
C4—C3—C8—C7	−2.1 (3)	C4'—C3'—C8'—C7'	0.4 (3)
S1—C3—C8—C7	171.76 (15)	S1'—C3'—C8'—C7'	−175.09 (16)
C4—C3—C8—N2	176.24 (18)	C4'—C3'—C8'—N2'	−177.00 (18)
S1—C3—C8—N2	−9.9 (3)	S1'—C3'—C8'—N2'	7.5 (3)
O6—N2—C8—C7	−47.1 (3)	O6'—N2'—C8'—C7'	45.3 (3)
O5—N2—C8—C7	131.3 (2)	O5'—N2'—C8'—C7'	−132.4 (2)
O6—N2—C8—C3	134.4 (2)	O6'—N2'—C8'—C3'	−137.2 (2)
O5—N2—C8—C3	−47.1 (3)	O5'—N2'—C8'—C3'	45.1 (3)
N1—C2—C9—C11	66.0 (2)	N1'—C2'—C9'—C11'	−68.0 (2)
C1—C2—C9—C11	−176.22 (17)	C1'—C2'—C9'—C11'	173.22 (17)
C10—C2—C9—C11	−55.4 (2)	C10'—C2'—C9'—C11'	54.2 (2)
N1—C2—C10—C13	−61.5 (2)	N1'—C2'—C10'—C13'	63.4 (2)
C1—C2—C10—C13	174.60 (16)	C1'—C2'—C10'—C13'	−172.35 (16)
C9—C2—C10—C13	56.6 (2)	C9'—C2'—C10'—C13'	−55.2 (2)
C2—C9—C11—C12	54.6 (2)	C2'—C9'—C11'—C12'	−55.5 (2)
C9—C11—C12—C13	−53.9 (2)	C9'—C11'—C12'—C13'	55.3 (2)
C11—C12—C13—C10	55.3 (3)	C11'—C12'—C13'—C10'	−55.7 (2)
C2—C10—C13—C12	−57.3 (2)	C2'—C10'—C13'—C12'	56.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4′	0.85 (3)	1.77 (3)	2.619 (2)	175 (3)
N1—H1N···O5	0.83 (3)	2.61 (3)	3.050 (2)	115 (2)
O3′—H3O′···O4	0.89 (3)	1.82 (3)	2.705 (2)	172 (3)
N1′—H1N′···O5′	0.83 (3)	2.53 (3)	2.999 (2)	117 (2)
N1′—H1N′···O5^i	0.83 (3)	2.40 (3)	3.214 (2)	168 (3)

Symmetry code: (i) x, −y+3/2, z+1/2.