research communications
H-pyran-2-yl]sulfanyl}nicotinonitrile
of 4,6-dimethyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2aChemistry Department, Faculty of Science, Helwan University, Cairo, Egypt, bPharmaceutical Chemistry Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt, and cInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany
*Correspondence e-mail: p.jones@tu-bs.de
In the title compound, C14H18N2O5S, the C—S bond lengths are unequal, with S—Cglucose = 1.8016 (15) Å and S—Cpyridyl = 1.7723 (13) Å. The hydrophilic glucose residues lie in the regions z ≃ 0.25 and 0.75. Four classical hydrogen bonds link the molecules to form layers parallel to the ab plane, from which the pyridyl rings project; pyridyl ring stacking parallel to the a axis links adjacent layers.
Keywords: crystal structure; pyridine; thioglucose.
CCDC reference: 1580696
1. Chemical context
The search for new anticancer chemotherapeutic agents continues to be an active area of research (Elgemeie, 2003; Elgemeie & Jones, 2004). In recent years nucleoside analogs have occupied a significant position in the search for effective chemotherapeutic agents, because many non-natural nucleoside derivatives have been shown to possess bioactivity (Elgemeie & Abou-Zeid, 2015). In the last few decades, pyridine derivatives have received considerable attention because of their wide-ranging applications as antimetabolic agents (Elgemeie et al., 2009). Recently, we reported that many pyridine thioglycosides showed strong cytotoxicity against several human cancer cell lines and block proliferation of various cancer cell lines (Elgemeie, Abou-Zeid et al., 2015). We also showed that thioglycosides involving pyridine and dihydropyridine groups exerted inhibitory effects on both DNA- and RNA-containing viruses and inhibitors of protein glycosylation, respectively (Elgemeie et al., 2010). In view of these observations and with the aim of identifying new anticancer agents with improved pharmacokinetic and safety profiles, we have synthesized some new non-classical nucleoside analogs incorporating pyridine thioglycosides.
We report here a novel one-step synthesis of a pyridine-2-thioglucoside derivative by reaction of the pyridine-2(1H)-thione derivative (1) with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2). Thus, (1) reacted with (2) in KOH/acetone to give a product for which two isomeric structures, (3) and (4), seemed possible, corresponding to two possible modes of glucosylation. After deprotection of the product (see Scheme), the final free sugar pyridinethione N-glucoside (5) or its regioisomer pyridine-2-thioglucoside (6) was obtained. Spectroscopic data cannot differentiate between these structures.
2. Structural commentary
The X-ray 6) as the product in the solid state. The molecule is shown in Fig. 1 and geometrical parameters are given in Table 1. The C—S bond lengths are markedly unequal, with S—Cglucose 1.8016 (15), S—Cpyridyl 1.7723 (13) Å. The main torsional are between the rings, as defined by the torsion angles N11—C12—S1—C1 = −2.08 (14) and C2—C1—S1—C12 = 152.98 (9)°.
indicated unambiguously the formation of the pyridine-2-thioglucoside (
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3. Supramolecular features
The glucose moieties of (6) occupy the regions at z ≃ 0.25 and 0.75. The layer structure of (6) is shown in Fig. 2. Each O—H donor forms one two-centre hydrogen bond (Table 2); the two most linear C—H⋯X interactions also lie within the layer, but are not drawn explicitly in Fig. 2. The same applies to the short contact S1⋯O5 ( − x, + y, − z) = 3.1417 (10) Å.
Adjacent layers are connected via the pyridyl rings, which project into the spaces between the hydrophilic layers and form π stacks parallel to the a axis. Adjacent rings in the stack are related by the twofold axis (operators 1 − x, y, 1 − z and 2 − x, y, 1 − z). The interplanar angles are 4.33 (5)°, the centroid-to-centroid distances are 3.96 and 3.72 Å, and the ring offsets are ca 1.26 and 0.94 Å; these cannot be expressed exactly because neighbouring rings are not exactly parallel.
4. Database survey
Perhaps surprisingly, a database search revealed only one other example of a pyridine ring with a thioglucose substituent at the 2-position, namely pyridyl thioglucose monohydrate (Nordenson & Jeffrey, 1980; refcode PYSGPR). This compound also shows a marked inequality between the S—C bond lengths (cf. Table 1); S—Cglucose is 1.793 (3), S—Cpyridyl is 1.759 (3) Å.
5. Synthesis and crystallization
To a solution of the pyridine-2-(1H)-thione (1) (1.64 gm, 0.01 mol) in aqueous potassium hydroxide (6 ml, 0.56 g, 0.01 mol) was added a solution of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (2) (4.52 g, 0.011 mol) in acetone (30 ml). The reaction mixture was stirred at room temperature until the reaction was judged complete by TLC (30 min to 2 h). The mixture was evaporated under reduced pressure at 313 K and the residue was washed with distilled water to remove the potassium bromide. The solid was collected by filtration and crystallized from ethanol to give compound (3) in 85% yield (m.p. 468 K). Dry gaseous ammonia was then passed through a solution of the protected thioglycoside (3) (0.5 g) in dry methanol (20 ml) at 273 K for 0.5 h, then the mixture was stirred at 273 K until completion of the reaction (TLC, 2–6 h). The mixture was evaporated at 313 K to give a solid residue, which was recrystallized from ethanol to give compound (6) in 85% yield (m.p. 482–483 K).
IR (KBr): 3600–3258 (OH), 2222 (CN) cm−1. 1H NMR (DMSO-d6): δ 2.22 (s, 3H, CH3), 2.31 (s, 3H, CH3), 3.15–3.80 (m, 6H, 2H-6′, H-5′, H-4′, H-3′, H-2′), 4.40 (d, J = 9.55 Hz, 2H, HO-2′ and HO-3′), 4.90 (s, 1H, HO-4′), 5.30 (s, 1H, HO-6′), 5.59 (d, J1,2 = 9.86 Hz, 1H, H-1′), 7.19 (s, 1H, pyridine H-5) ppm. 13C NMR: δ 20.7 (CH3), 22.9 (CH3), 61.0 (C6′), 68.9 (C4′), 72.7 (C2′), 75.9 (C3′), 80.7 (C5′), 83.7 (C1′), 103.2 (C3), 116.0 (CN), 119.7 (C5), 149.2 (C4), 159.0 (C6), 164.0 (C2) ppm.
6. Refinement
Crystal data, data collection and structure . The as initially found by the diffractometer program was P21, with two independent but virtually identical molecules in the It became apparent that the two molecules formed layer structures independent of each other, and were related by a translation vector (0.5, 0.5, 0.5). The checkCIF program also indicated that the true should be centred, with a 100% fit and a small deviation. The same cell was retained for ease of checking, and the and repeated in I2. The was entirely satisfactory, and corresponds to the structure presented here. However, the reflections with (h + k + l) odd, which are required to be systematically absent in I2, seemed to be quite definitely present. We are unable to explain this anomaly. The HKL file appended to the contains these reflections.
details are summarized in Table 3
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Crystal data, data collection and structure . OH hydrogen atoms were refined freely but with an O—H distance restraint (SADI). Methyl groups were refined as idealized rigid groups allowed to rotate but not tip (AFIX 137), with C—H 0.98 Å and H—C—H 109.5°. Other hydrogen atoms were included using a riding model starting from calculated positions (C—Haromatic 0.95, C—Hmethylene 0.99, C—Hmethine 1.00 Å).
details are summarized in Table 2 was determined by the unambiguous of −0.008 (8) (ParsonsSupporting information
CCDC reference: 1580696
https://doi.org/10.1107/S2056989017015213/qm2120sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017015213/qm2120Isup2.hkl
Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell
CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015).C14H18N2O5S | F(000) = 688 |
Mr = 326.36 | Dx = 1.379 Mg m−3 |
Monoclinic, I2 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.66978 (18) Å | Cell parameters from 46975 reflections |
b = 8.72860 (13) Å | θ = 2.7–30.9° |
c = 23.7524 (4) Å | µ = 0.23 mm−1 |
β = 98.7356 (16)° | T = 100 K |
V = 1571.69 (5) Å3 | Block, colourless |
Z = 4 | 0.40 × 0.35 × 0.20 mm |
Oxford Diffraction Xcalibur Eos diffractometer | 4741 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 4590 reflections with I > 2σ(I) |
Detector resolution: 16.1419 pixels mm-1 | Rint = 0.027 |
ω–scan | θmax = 31.2°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015) | h = −10→11 |
Tmin = 0.980, Tmax = 1.000 | k = −12→12 |
84844 measured reflections | l = −34→33 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.0354P)2 + 0.4674P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.063 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.30 e Å−3 |
4741 reflections | Δρmin = −0.17 e Å−3 |
217 parameters | Absolute structure: Flack x determined using 2066 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
7 restraints | Absolute structure parameter: −0.008 (8) |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.59062 (4) | 0.54939 (4) | 0.37504 (2) | 0.01953 (8) | |
C1 | 0.57772 (17) | 0.35296 (17) | 0.35150 (5) | 0.0175 (2) | |
H1 | 0.557606 | 0.284848 | 0.383749 | 0.021* | |
O1 | 0.74310 (12) | 0.31545 (12) | 0.33376 (4) | 0.0183 (2) | |
C2 | 0.42750 (17) | 0.33167 (17) | 0.30152 (5) | 0.0177 (3) | |
H2 | 0.444291 | 0.404110 | 0.270164 | 0.021* | |
O2 | 0.26172 (13) | 0.35885 (13) | 0.31878 (4) | 0.0200 (2) | |
H02 | 0.223 (4) | 0.438 (3) | 0.3050 (12) | 0.054 (8)* | |
C3 | 0.42986 (17) | 0.16706 (17) | 0.27975 (5) | 0.0184 (2) | |
H3 | 0.399828 | 0.095244 | 0.309645 | 0.022* | |
O3 | 0.30583 (13) | 0.14881 (14) | 0.22910 (4) | 0.0226 (2) | |
H03 | 0.207 (3) | 0.161 (3) | 0.2365 (9) | 0.033 (6)* | |
C4 | 0.61090 (18) | 0.12809 (18) | 0.26570 (6) | 0.0185 (3) | |
H4 | 0.636616 | 0.194695 | 0.233704 | 0.022* | |
O4 | 0.61422 (15) | −0.02842 (14) | 0.24885 (5) | 0.0250 (2) | |
H04 | 0.672 (3) | −0.035 (3) | 0.2237 (9) | 0.039 (6)* | |
C5 | 0.74991 (17) | 0.15622 (18) | 0.31794 (5) | 0.0186 (2) | |
H5 | 0.722628 | 0.091101 | 0.350129 | 0.022* | |
C6 | 0.93568 (18) | 0.12113 (19) | 0.30688 (5) | 0.0210 (3) | |
H6A | 1.021081 | 0.174340 | 0.335809 | 0.025* | |
H6B | 0.957132 | 0.009636 | 0.311368 | 0.025* | |
O5 | 0.96641 (13) | 0.16663 (14) | 0.25148 (4) | 0.0208 (2) | |
H05 | 0.957 (3) | 0.256 (2) | 0.2480 (11) | 0.043 (7)* | |
N11 | 0.71744 (19) | 0.38506 (16) | 0.46739 (5) | 0.0247 (3) | |
C12 | 0.68518 (18) | 0.52490 (16) | 0.44732 (5) | 0.0193 (3) | |
C13 | 0.7223 (2) | 0.65733 (19) | 0.48057 (6) | 0.0219 (3) | |
C14 | 0.8011 (2) | 0.64238 (19) | 0.53789 (6) | 0.0235 (3) | |
C15 | 0.8355 (2) | 0.4955 (2) | 0.55786 (6) | 0.0274 (3) | |
H15 | 0.889755 | 0.479840 | 0.596114 | 0.033* | |
C16 | 0.7915 (2) | 0.3696 (2) | 0.52236 (6) | 0.0290 (3) | |
C17 | 0.6799 (3) | 0.8053 (2) | 0.45591 (7) | 0.0313 (4) | |
N12 | 0.6448 (3) | 0.9219 (2) | 0.43492 (7) | 0.0491 (5) | |
C18 | 0.8435 (3) | 0.7795 (2) | 0.57556 (7) | 0.0357 (4) | |
H18A | 0.876528 | 0.745852 | 0.615104 | 0.054* | |
H18B | 0.739865 | 0.846339 | 0.572717 | 0.054* | |
H18C | 0.941903 | 0.835962 | 0.563468 | 0.054* | |
C19 | 0.8230 (4) | 0.2094 (2) | 0.54374 (8) | 0.0472 (5) | |
H19A | 0.779315 | 0.137031 | 0.513317 | 0.071* | |
H19B | 0.760624 | 0.192842 | 0.576301 | 0.071* | |
H19C | 0.949717 | 0.193415 | 0.555621 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01731 (15) | 0.02917 (15) | 0.01144 (12) | −0.00026 (13) | 0.00001 (10) | 0.00067 (12) |
C1 | 0.0108 (6) | 0.0311 (7) | 0.0110 (5) | −0.0011 (5) | 0.0029 (4) | −0.0017 (5) |
O1 | 0.0094 (4) | 0.0321 (5) | 0.0138 (4) | −0.0017 (4) | 0.0028 (3) | −0.0016 (4) |
C2 | 0.0091 (6) | 0.0334 (7) | 0.0107 (5) | −0.0015 (5) | 0.0023 (4) | −0.0006 (5) |
O2 | 0.0097 (4) | 0.0329 (5) | 0.0181 (4) | 0.0011 (4) | 0.0045 (3) | 0.0002 (4) |
C3 | 0.0094 (6) | 0.0328 (7) | 0.0132 (5) | −0.0023 (5) | 0.0029 (4) | −0.0023 (5) |
O3 | 0.0084 (4) | 0.0429 (6) | 0.0162 (4) | −0.0026 (4) | 0.0014 (3) | −0.0066 (4) |
C4 | 0.0093 (6) | 0.0329 (7) | 0.0136 (5) | −0.0026 (5) | 0.0029 (4) | −0.0033 (5) |
O4 | 0.0159 (5) | 0.0371 (6) | 0.0239 (5) | −0.0036 (4) | 0.0095 (4) | −0.0100 (5) |
C5 | 0.0114 (6) | 0.0322 (6) | 0.0123 (5) | −0.0006 (5) | 0.0025 (4) | −0.0015 (5) |
C6 | 0.0104 (6) | 0.0404 (8) | 0.0124 (5) | 0.0011 (5) | 0.0018 (4) | −0.0012 (5) |
O5 | 0.0113 (4) | 0.0378 (6) | 0.0138 (4) | −0.0013 (4) | 0.0040 (3) | −0.0025 (4) |
N11 | 0.0303 (7) | 0.0304 (6) | 0.0123 (5) | −0.0068 (5) | −0.0003 (5) | 0.0028 (5) |
C12 | 0.0153 (6) | 0.0318 (8) | 0.0107 (5) | −0.0027 (5) | 0.0022 (4) | 0.0005 (5) |
C13 | 0.0213 (7) | 0.0316 (7) | 0.0131 (6) | −0.0011 (6) | 0.0039 (5) | −0.0001 (5) |
C14 | 0.0249 (7) | 0.0330 (8) | 0.0127 (6) | −0.0042 (6) | 0.0030 (5) | −0.0021 (5) |
C15 | 0.0331 (8) | 0.0353 (7) | 0.0124 (6) | −0.0069 (6) | −0.0010 (5) | 0.0010 (5) |
C16 | 0.0397 (9) | 0.0319 (8) | 0.0139 (6) | −0.0065 (7) | −0.0009 (6) | 0.0042 (6) |
C17 | 0.0441 (10) | 0.0340 (8) | 0.0151 (6) | 0.0055 (7) | 0.0029 (6) | −0.0042 (6) |
N12 | 0.0849 (15) | 0.0372 (9) | 0.0232 (7) | 0.0143 (9) | 0.0022 (8) | −0.0021 (6) |
C18 | 0.0511 (11) | 0.0371 (9) | 0.0175 (7) | −0.0039 (8) | 0.0005 (7) | −0.0059 (6) |
C19 | 0.0847 (17) | 0.0335 (9) | 0.0182 (7) | −0.0065 (10) | −0.0093 (8) | 0.0069 (7) |
S1—C12 | 1.7723 (13) | C6—H6A | 0.9900 |
S1—C1 | 1.8016 (15) | C6—H6B | 0.9900 |
C1—O1 | 1.4338 (16) | O5—H05 | 0.79 (2) |
C1—C2 | 1.5348 (17) | N11—C12 | 1.3201 (19) |
C1—H1 | 1.0000 | N11—C16 | 1.3492 (19) |
O1—C5 | 1.4428 (18) | C12—C13 | 1.405 (2) |
C2—O2 | 1.4141 (16) | C13—C14 | 1.4092 (19) |
C2—C3 | 1.528 (2) | C13—C17 | 1.435 (2) |
C2—H2 | 1.0000 | C14—C15 | 1.379 (2) |
O2—H02 | 0.80 (2) | C14—C18 | 1.500 (2) |
C3—O3 | 1.4247 (16) | C15—C16 | 1.394 (2) |
C3—C4 | 1.5152 (18) | C15—H15 | 0.9500 |
C3—H3 | 1.0000 | C16—C19 | 1.495 (2) |
O3—H03 | 0.809 (19) | C17—N12 | 1.147 (2) |
C4—O4 | 1.4249 (18) | C18—H18A | 0.9800 |
C4—C5 | 1.5280 (18) | C18—H18B | 0.9800 |
C4—H4 | 1.0000 | C18—H18C | 0.9800 |
O4—H04 | 0.800 (19) | C19—H19A | 0.9800 |
C5—C6 | 1.5187 (18) | C19—H19B | 0.9800 |
C5—H5 | 1.0000 | C19—H19C | 0.9800 |
C6—O5 | 1.4279 (16) | ||
C12—S1—C1 | 100.43 (6) | O5—C6—H6A | 108.9 |
O1—C1—C2 | 109.80 (10) | C5—C6—H6A | 108.9 |
O1—C1—S1 | 107.40 (9) | O5—C6—H6B | 108.9 |
C2—C1—S1 | 110.77 (10) | C5—C6—H6B | 108.9 |
O1—C1—H1 | 109.6 | H6A—C6—H6B | 107.8 |
C2—C1—H1 | 109.6 | C6—O5—H05 | 110.3 (19) |
S1—C1—H1 | 109.6 | C12—N11—C16 | 118.04 (14) |
C1—O1—C5 | 111.41 (10) | N11—C12—C13 | 123.16 (13) |
O2—C2—C3 | 108.25 (11) | N11—C12—S1 | 119.22 (10) |
O2—C2—C1 | 110.96 (10) | C13—C12—S1 | 117.62 (11) |
C3—C2—C1 | 109.24 (11) | C12—C13—C14 | 119.18 (14) |
O2—C2—H2 | 109.5 | C12—C13—C17 | 119.82 (13) |
C3—C2—H2 | 109.5 | C14—C13—C17 | 121.00 (15) |
C1—C2—H2 | 109.5 | C15—C14—C13 | 116.75 (14) |
C2—O2—H02 | 109 (2) | C15—C14—C18 | 121.60 (13) |
O3—C3—C4 | 107.80 (10) | C13—C14—C18 | 121.64 (15) |
O3—C3—C2 | 110.49 (11) | C14—C15—C16 | 120.56 (14) |
C4—C3—C2 | 110.12 (11) | C14—C15—H15 | 119.7 |
O3—C3—H3 | 109.5 | C16—C15—H15 | 119.7 |
C4—C3—H3 | 109.5 | N11—C16—C15 | 122.29 (15) |
C2—C3—H3 | 109.5 | N11—C16—C19 | 116.40 (15) |
C3—O3—H03 | 109.1 (16) | C15—C16—C19 | 121.31 (14) |
O4—C4—C3 | 109.46 (12) | N12—C17—C13 | 178.31 (17) |
O4—C4—C5 | 110.01 (12) | C14—C18—H18A | 109.5 |
C3—C4—C5 | 109.57 (11) | C14—C18—H18B | 109.5 |
O4—C4—H4 | 109.3 | H18A—C18—H18B | 109.5 |
C3—C4—H4 | 109.3 | C14—C18—H18C | 109.5 |
C5—C4—H4 | 109.3 | H18A—C18—H18C | 109.5 |
C4—O4—H04 | 108.6 (19) | H18B—C18—H18C | 109.5 |
O1—C5—C6 | 108.14 (11) | C16—C19—H19A | 109.5 |
O1—C5—C4 | 108.53 (11) | C16—C19—H19B | 109.5 |
C6—C5—C4 | 112.61 (11) | H19A—C19—H19B | 109.5 |
O1—C5—H5 | 109.2 | C16—C19—H19C | 109.5 |
C6—C5—H5 | 109.2 | H19A—C19—H19C | 109.5 |
C4—C5—H5 | 109.2 | H19B—C19—H19C | 109.5 |
O5—C6—C5 | 113.19 (11) | ||
C12—S1—C1—O1 | −87.12 (9) | C3—C4—C5—C6 | −179.39 (13) |
C12—S1—C1—C2 | 152.98 (9) | O1—C5—C6—O5 | −81.24 (14) |
C2—C1—O1—C5 | −63.63 (14) | C4—C5—C6—O5 | 38.67 (18) |
S1—C1—O1—C5 | 175.85 (8) | C16—N11—C12—C13 | −0.8 (2) |
O1—C1—C2—O2 | 176.40 (11) | C16—N11—C12—S1 | 179.18 (12) |
S1—C1—C2—O2 | −65.14 (13) | C1—S1—C12—N11 | −2.08 (14) |
O1—C1—C2—C3 | 57.13 (14) | C1—S1—C12—C13 | 177.90 (11) |
S1—C1—C2—C3 | 175.59 (8) | N11—C12—C13—C14 | 1.4 (2) |
O2—C2—C3—O3 | 66.09 (13) | S1—C12—C13—C14 | −178.62 (11) |
C1—C2—C3—O3 | −172.97 (10) | N11—C12—C13—C17 | −178.71 (16) |
O2—C2—C3—C4 | −174.93 (11) | S1—C12—C13—C17 | 1.31 (19) |
C1—C2—C3—C4 | −54.00 (14) | C12—C13—C14—C15 | −0.6 (2) |
O3—C3—C4—O4 | −62.97 (14) | C17—C13—C14—C15 | 179.51 (16) |
C2—C3—C4—O4 | 176.42 (10) | C12—C13—C14—C18 | −179.89 (15) |
O3—C3—C4—C5 | 176.33 (12) | C17—C13—C14—C18 | 0.2 (2) |
C2—C3—C4—C5 | 55.72 (15) | C13—C14—C15—C16 | −0.7 (3) |
C1—O1—C5—C6 | −173.06 (10) | C18—C14—C15—C16 | 178.65 (17) |
C1—O1—C5—C4 | 64.49 (13) | C12—N11—C16—C15 | −0.5 (3) |
O4—C4—C5—O1 | 179.92 (10) | C12—N11—C16—C19 | 178.95 (18) |
C3—C4—C5—O1 | −59.70 (14) | C14—C15—C16—N11 | 1.3 (3) |
O4—C4—C5—C6 | 60.23 (16) | C14—C15—C16—C19 | −178.17 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H02···O3i | 0.80 (2) | 2.01 (2) | 2.7909 (16) | 165 (3) |
O3—H03···O5ii | 0.81 (2) | 1.93 (2) | 2.7394 (14) | 174 (2) |
O4—H04···O1iii | 0.80 (2) | 2.06 (2) | 2.7490 (15) | 144 (2) |
O5—H05···O4iv | 0.79 (2) | 1.96 (2) | 2.7324 (18) | 165 (3) |
C2—H2···O5iv | 1.00 | 2.47 | 3.3326 (19) | 144 |
C5—H5···N12v | 1.00 | 2.64 | 3.638 (2) | 179 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+3/2, y−1/2, −z+1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) x, y−1, z. |
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