research communications
d]thiazol-2-yl)-6-(methylsulfanyl)pyrimidin-2-yl](phenylsulfonyl)azanide dimethylformamide monosolvate hemihydrate
of potassium [4-amino-5-(benzo[aChemistry Department, Faculty of Science, Helwan University, Cairo, Egypt, and bInstitut für Anorganische und Analytische Chemie, Technische Universität Braunschweig, Hagenring 30, D-38106 Braunschweig, Germany
*Correspondence e-mail: p.jones@tu-bs.de
The title compound, K+·C18H14N5O2S3−·C3H7NO·0.5H2O, was obtained in a reaction designed to deliver a neutral 2-pyrimidylbenzothiazole. The anion is deprotonated at the sulfonamide nitrogen. The of the title compound contains two potassium cations, two anions, two molecules of DMF and one of water. The anions display some conformational differences but each contains an intramolecular N—H⋯Nbenzothiazole hydrogen bond. The potassium ions both display a highly irregular six-coordination, different for each potassium ion. The anions, together with the DMF and water molecules, are linked by four classical hydrogen bonds to form chains parallel to the b-axis direction.
Keywords: crystal structure; benzothiazole; sulfonamide; pyrimidine; hydrogen bonding.
CCDC reference: 1896740
1. Chemical context
Benzothiazoles are versatile heterocyclic biologically active compounds that are common in a variety of pharmaceutical preparations (Azzam et al., 2017a,b). These compounds are of great importance in the field of medicinal chemistry because of their remarkable pharmacological potential (Keri et al., 2015). Benzothiazole derivatives show a high degree of structural diversity that has proved beneficial in the search for new therapeutic agents (Gill et al., 2015). Research in benzothiazole-based medicinal chemistry has rapidly become an active topic, since numerous benzothiazole-based compounds have been widely used as clinical drugs to treat various types of diseases with high therapeutic potency (Sharma et al., 2013). The medicinal properties associated with benzothiazole-related drugs have encouraged medicinal chemists to synthesize a large number of new therapeutics (Elgemeie & Elghandour, 1990; Elgemeie et al., 2000a,b). In recent years, 2-pyrimidylbenzothiazoles have appeared as an important pharmacological class in the development of anti-tumor agents (Das et al., 2003); their promising biological profile and synthetic accessibility have been attractive in their design and development as potential chemotherapeutics. In order to access this class of compounds in high yield and to introduce diversity, a variety of new synthetic methods has been invented (Seenaiah et al., 2014). Recently, we have described the syntheses of various antimetabolites starting from heterocyclic and acyclic cyanoketene dithioacetals (Elgemeie et al., 2015, 2016, 2017). As part of this program the reaction of 2-(benzo[d]thiazol-2-yl)-3,3-bis(methylthio)acrylonitrile (2) with N-(diaminomethylene)benzenesulfonamide (3) was studied (Fig. 1). The reaction between 2 and 3 in KOH/dioxane gave a product that was crystallized from DMF and identified by X-ray crystallography as the title compound, 5, rather than the expected neutral 2-pyrimidylbenzothiazole derivative, 4. Compound 4 appears to be formed, at least in part, on dissolving 5 in deuterated DMSO; 1H NMR measurements showed the free NH proton at δ 11.50 ppm. However, we have still been unable to isolate and crystallize derivative 4.
The formation of 5 from the reaction of 2 and 3 is assumed to proceed via initial addition of the amino group of 3 to the double bond of 2, followed by elimination of CH3SH and via addition of the amino group to the cyano group of benzothiazole to give the product 4, which separated as its potassium salt 5 in the presence of KOH in the reaction medium. The 1H NMR spectra of the product 4, formed in part in solution in deuterated DMSO, revealed the presence of a pyrimidine methylthio group at δ = 2.19 ppm and an amino group at δ = 8.49 ppm in solution. Compound 5 and its derivatives showed interesting preclinical antiviral biological results compared to current antiviral drugs and are currently being patented (Elgemeie et al., 2018).
2. Structural commentary
The X-ray 5 in the solid state. The molecular structure of compound 5 is illustrated in Fig. 2. The contains two potassium cations, two anions of 4 deprotonated at the sulfonamide nitrogen, two molecules of DMF and one of water; it was chosen arbitrarily in an attempt to maximize the number of weak interactions (bonds to potassium, hydrogen bonds) within this unit.
indicated the exclusive presence of structureThe potassium ions both display a highly irregular six-coordination; all K—N and K—O contacts (Table 1) are < 2.92 Å, and the next longest are > 3.33 Å. The atom K1 is coordinated by the pyrimidine nitrogen atom N2 and the deprotonated sulfonamide nitrogen N5, the sulfonamide oxygen atom O1′ and the water oxygen O1W within the and by the sulfonamide oxygen atom O2′ and the DMF oxygen O92 at (−x + 1, −y + 1, −z + 1). The atom K2 is coordinated by N2′, N5′ and both DMF oxygen atoms within the plus O2 at (−x + 1, −y + 1, −z + 1) and O1 at (x, y − 1, z). The angles subtended by the chelating anions via N2/N5 are particularly narrow. The bridging nature of O92 is shown in Fig. 3.
Each anion displays an intramolecular hydrogen bond (N4—H01⋯N3 and N4′—H01′⋯N3′; Table 2), forming an S(6) ring motif. The anions display some differences in conformation; the angle between the benzothiazole ring (seven atoms) and the pyrimidine ring plus immediate substituents (ten atoms) is 20.56 (5)° for anion 1 (unprimed atoms) but 42.20 (2)° for anion 2 (primed atoms). Comparing the torsion angles in Table 1, it may be seen that the signs of the torsion angles C9—C8—C2—S1 are different for the two anions [22.06 (18) and −42.51 (16)°]. A molecular fit of the ten atoms of the pyrimidine ring, inverting one anion, gives an r.m.s. deviation of 0.03 Å (Fig. 4); the benzothiazole rings are then a better fit, but the phenyl rings of the sulfonamide groups then point to opposite sides in the two anions, cf. torsion angle C10—N5—S3—C13 is 62.49 (11)°, and 65.28 (11)° in the non-inverted system.
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3. Supramolecular features
Classical hydrogen bonds are shown in Table 2. These four hydrogen bonds combined with the contacts at the potassium ions give a highly complex packing pattern. If the potassium ions are omitted, a much more simple pattern emerges; the residues are linked via the water molecules to form chains parallel to the b-axis direction, two of which are shown in Fig. 5.
4. Database survey
A search of the Cambridge Structural Database (CSD, V5.40, November 2018; Groom et al., 2016) gave 47 hits (including ten duplicated structures) for the fragment consisting of a pyrimidine ring system bearing a two-coordinate, and thus negatively charged, nitrogen substituent at the ring carbon between the two nitrogen atoms, with the nitrogen substituent forming part of a sulfonamide system. The hits included a silver salt (ASULDZ; Cook & Turner, 1975) and a sodium salt (JUBGUI/01; Hannan & Talukdar, 1992; Patel, 1995).
5. Synthesis and crystallization
Synthesis of potassium [4-amino-5-(benzo[d]thiazol-2-yl)-6-(methylsulfanyl)pyrimidin-2-yl](phenylsulfonyl)azanide dimethylformamide monosolvate hemihydrate (5):
The reaction pathway is illustrated in Fig. 1. 2-(Benzo[d]thiazole-2-yl)-3,3-bis(methylthio)acrylonitrile (2) (0.01 mol) was added to a stirred solution of the N-(diaminomethylene)benzenesulfonamide (3) (0.01 mol) in dry dioxane (20 ml) containing potassium hydroxide (0.01 mol); the reaction mixture was refluxed for 2 h. After completion of the reaction (TLC), the solid precipitate was filtered off, and then recrystallized from DMF/H2O to give colourless block-like crystals of compound 5, the potassium salt of compound 4, in 75% yield (m.p. = 517 K). IR (KBr, cm−1): ν 3431 and 3874 (NH, NH2). 1H NMR (400 MHz, DMSO-d6): δ 2.19 (s, 3H, SCH3), 7.32–7.39 (m, 4H, 3CH-phenyl, CH benzothiazole), 7.46 (t, 1H, J = 8.0 Hz, CH benzothiazole), 7.83–7.85 (m, 2H, 2CH-phenyl), 7.92 (d, 1H, J = 8.0 Hz, CH benzothiazole), 8.01 (d, 1H, J = 8.0 Hz, CH benzothiazole), 8.49 (s, br, 2H, NH2), 11.50 (s, br, 1H, NH).
6. Refinement
Crystal data, data collection and structure . The NH and OH hydrogen atoms were identified in difference-Fourier maps and refined freely. Methyl groups were identified from difference-Fourier maps, idealized and refined as rigid groups [C—H = 0.98 Å, H—C—H = 109.5° with Uiso(H) = 1.5Ueq(C-methyl)], and allowed to rotate but not to tip (AFIX 137). Other hydrogen atoms were included using a riding model starting from calculated positions: C—Haromatic = 0.95 Å with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 3
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Supporting information
CCDC reference: 1896740
https://doi.org/10.1107/S2056989019002275/su5477sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019002275/su5477Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 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).K+·C18H14N5O2S3−·C3H7NO·0.5H2O | Z = 4 |
Mr = 549.72 | F(000) = 1140 |
Triclinic, P1 | Dx = 1.514 Mg m−3 |
a = 11.8407 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6001 (4) Å | Cell parameters from 60104 reflections |
c = 18.8671 (5) Å | θ = 2.4–30.6° |
α = 90.160 (2)° | µ = 0.52 mm−1 |
β = 102.361 (2)° | T = 100 K |
γ = 117.933 (3)° | Block, colourless |
V = 2411.88 (13) Å3 | 0.35 × 0.25 × 0.25 mm |
Oxford Diffraction Xcalibur Eos diffractometer | 13912 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 11954 reflections with I > 2σ(I) |
Detector resolution: 16.1419 pixels mm-1 | Rint = 0.047 |
ω–scan | θmax = 30.0°, θmin = 2.2° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | h = −16→16 |
Tmin = 0.994, Tmax = 1.000 | k = −17→17 |
256622 measured reflections | l = −26→26 |
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)] = 0.030 | Hydrogen site location: mixed |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0331P)2 + 1.360P] where P = (Fo2 + 2Fc2)/3 |
13912 reflections | (Δ/σ)max = 0.002 |
652 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.5026 (0.0024) x + 0.9321 (0.0047) y + 8.4090 (0.0051) z = 6.8996 (0.0032) * -0.0075 (0.0009) C2 * 0.0127 (0.0009) N3 * 0.0119 (0.0012) C3A * -0.0103 (0.0011) C4 * -0.0129 (0.0011) C5 * 0.0036 (0.0011) C6 * 0.0057 (0.0010) C7 * 0.0136 (0.0012) C7A * -0.0168 (0.0007) S1 Rms deviation of fitted atoms = 0.0113 5.7089 (0.0026) x + 5.0746 (0.0027) y + 5.8404 (0.0040) z = 8.9926 (0.0015) Angle to previous plane (with approximate esd) = 20.556 ( 0.046 ) * 0.0683 (0.0011) C8 * 0.0132 (0.0010) C9 * 0.0105 (0.0010) C10 * -0.0228 (0.0011) C11 * -0.0190 (0.0009) N1 * -0.0234 (0.0010) N2 * 0.1204 (0.0009) C2 * -0.1062 (0.0006) S2 * 0.0646 (0.0008) N5 * -0.1055 (0.0009) N4 -0.1967 (0.0016) C12 -0.2593 (0.0011) S3 Rms deviation of fitted atoms = 0.0689 =============================================================================== - 2.2187 (0.0034) x + 11.9323 (0.0012) y - 3.9110 (0.0057) z = 2.1027 (0.0024) * 0.0421 (0.0009) C2' * -0.0030 (0.0009) N3' * -0.0322 (0.0011) C3A' * -0.0032 (0.0011) C4' * 0.0107 (0.0011) C5' * 0.0163 (0.0011) C6' * 0.0101 (0.0010) C7' * -0.0308 (0.0011) C7A' * -0.0099 (0.0007) S1' Rms deviation of fitted atoms = 0.0220 4.0185 (0.0027) x + 7.7469 (0.0023) y + 2.9794 (0.0039) z = 6.0513 (0.0008) Angle to previous plane (with approximate esd) = 42.200 ( 0.021 ) * -0.0154 (0.0011) C8' * 0.0164 (0.0010) C9' * 0.0066 (0.0010) C10' * 0.0299 (0.0010) C11' * 0.0483 (0.0009) N1' * 0.0253 (0.0009) N2' * -0.1309 (0.0009) C2' * 0.0515 (0.0006) S2' * -0.1005 (0.0008) N5' * 0.0688 (0.0008) N4' -0.2532 (0.0017) C12' 0.1802 (0.0010) S3' Rms deviation of fitted atoms = 0.0625 =============================================================================== |
x | y | z | Uiso*/Ueq | ||
S1 | 0.67977 (4) | 1.02828 (3) | 0.09802 (2) | 0.01751 (7) | |
S2 | 0.47162 (3) | 1.04245 (3) | 0.15477 (2) | 0.01496 (6) | |
S3 | 0.31676 (3) | 0.90940 (3) | 0.39554 (2) | 0.01143 (6) | |
C2 | 0.63692 (12) | 0.90552 (11) | 0.15096 (6) | 0.0128 (2) | |
C3A | 0.73099 (13) | 0.85659 (11) | 0.07477 (7) | 0.0142 (2) | |
C4 | 0.77389 (14) | 0.78717 (12) | 0.04155 (7) | 0.0191 (3) | |
H4 | 0.762989 | 0.712529 | 0.057998 | 0.023* | |
C5 | 0.83241 (14) | 0.82984 (13) | −0.01570 (7) | 0.0202 (3) | |
H5 | 0.862215 | 0.784025 | −0.038767 | 0.024* | |
C6 | 0.84838 (14) | 0.93991 (13) | −0.04020 (7) | 0.0198 (3) | |
H6 | 0.889986 | 0.967721 | −0.079226 | 0.024* | |
C7 | 0.80507 (14) | 1.00885 (12) | −0.00895 (7) | 0.0189 (3) | |
H7 | 0.814762 | 1.082683 | −0.026224 | 0.023* | |
C7A | 0.74648 (13) | 0.96563 (11) | 0.04907 (7) | 0.0149 (2) | |
C8 | 0.57484 (12) | 0.89569 (10) | 0.21128 (6) | 0.0121 (2) | |
C9 | 0.50259 (12) | 0.95499 (10) | 0.22093 (6) | 0.0121 (2) | |
C10 | 0.46477 (12) | 0.87455 (11) | 0.32734 (6) | 0.0123 (2) | |
C11 | 0.57609 (12) | 0.81497 (11) | 0.26460 (6) | 0.0126 (2) | |
C12 | 0.37416 (14) | 1.08905 (12) | 0.19405 (7) | 0.0172 (2) | |
H12A | 0.417727 | 1.120507 | 0.245597 | 0.026* | |
H12B | 0.286843 | 1.019598 | 0.190301 | 0.026* | |
H12C | 0.364720 | 1.152476 | 0.167707 | 0.026* | |
C13 | 0.17010 (12) | 0.82029 (11) | 0.32687 (6) | 0.0134 (2) | |
C14 | 0.11572 (15) | 0.69479 (12) | 0.32221 (8) | 0.0217 (3) | |
H14 | 0.159533 | 0.658842 | 0.352897 | 0.026* | |
C15 | −0.00368 (15) | 0.62278 (13) | 0.27195 (8) | 0.0260 (3) | |
H15 | −0.041467 | 0.537174 | 0.268056 | 0.031* | |
C16 | −0.06766 (14) | 0.67590 (14) | 0.22751 (8) | 0.0232 (3) | |
H16 | −0.149850 | 0.626424 | 0.193940 | 0.028* | |
C17 | −0.01210 (14) | 0.80064 (13) | 0.23196 (8) | 0.0219 (3) | |
H17 | −0.055603 | 0.836490 | 0.200925 | 0.026* | |
C18 | 0.10750 (13) | 0.87374 (12) | 0.28186 (7) | 0.0172 (2) | |
H18 | 0.145806 | 0.959352 | 0.285031 | 0.021* | |
N1 | 0.44791 (11) | 0.94544 (9) | 0.27717 (6) | 0.0132 (2) | |
N2 | 0.52377 (11) | 0.80718 (9) | 0.32239 (6) | 0.0135 (2) | |
N3 | 0.67040 (11) | 0.82571 (10) | 0.13235 (6) | 0.0148 (2) | |
N4 | 0.63003 (12) | 0.74264 (10) | 0.26054 (6) | 0.0176 (2) | |
H02 | 0.6135 (19) | 0.6870 (18) | 0.2900 (11) | 0.033 (5)* | |
H01 | 0.651 (2) | 0.7365 (18) | 0.2208 (11) | 0.034 (5)* | |
N5 | 0.41916 (11) | 0.86521 (10) | 0.38931 (6) | 0.0137 (2) | |
O1 | 0.35584 (9) | 1.03538 (8) | 0.38428 (5) | 0.01534 (17) | |
O2 | 0.28269 (9) | 0.87920 (8) | 0.46485 (5) | 0.01566 (18) | |
S1' | 0.61437 (3) | 0.29511 (3) | 0.01676 (2) | 0.01725 (7) | |
S2' | 0.54376 (3) | 0.46946 (3) | 0.09428 (2) | 0.01721 (7) | |
S3' | 0.46192 (3) | 0.42692 (3) | 0.35846 (2) | 0.01176 (6) | |
C2' | 0.72463 (12) | 0.34847 (11) | 0.10370 (6) | 0.0122 (2) | |
C3A' | 0.85618 (13) | 0.34467 (11) | 0.03647 (7) | 0.0145 (2) | |
C4' | 0.97234 (14) | 0.36291 (13) | 0.01881 (7) | 0.0193 (3) | |
H4' | 1.051620 | 0.390641 | 0.055865 | 0.023* | |
C5' | 0.97023 (15) | 0.34001 (13) | −0.05340 (8) | 0.0209 (3) | |
H5' | 1.048490 | 0.351042 | −0.065639 | 0.025* | |
C6' | 0.85444 (15) | 0.30083 (12) | −0.10871 (7) | 0.0209 (3) | |
H6' | 0.855166 | 0.285520 | −0.157894 | 0.025* | |
C7' | 0.73941 (15) | 0.28421 (12) | −0.09258 (7) | 0.0198 (3) | |
H7' | 0.661289 | 0.259304 | −0.130140 | 0.024* | |
C7A' | 0.74080 (13) | 0.30496 (11) | −0.01957 (7) | 0.0150 (2) | |
C8' | 0.68045 (12) | 0.36129 (10) | 0.16870 (6) | 0.0115 (2) | |
C9' | 0.59510 (12) | 0.40880 (10) | 0.17095 (6) | 0.0120 (2) | |
C10' | 0.58805 (12) | 0.36622 (10) | 0.28789 (6) | 0.0114 (2) | |
C11' | 0.72036 (12) | 0.32086 (10) | 0.23520 (6) | 0.0117 (2) | |
C12' | 0.41439 (15) | 0.48795 (13) | 0.11841 (7) | 0.0206 (3) | |
H12D | 0.348305 | 0.410299 | 0.129017 | 0.031* | |
H12E | 0.372818 | 0.515917 | 0.077628 | 0.031* | |
H12F | 0.451606 | 0.547696 | 0.161728 | 0.031* | |
C13' | 0.31457 (13) | 0.37337 (12) | 0.28815 (6) | 0.0144 (2) | |
C14' | 0.24643 (13) | 0.25133 (12) | 0.26169 (7) | 0.0163 (2) | |
H14' | 0.280816 | 0.199034 | 0.279043 | 0.020* | |
C15' | 0.12741 (14) | 0.20642 (13) | 0.20955 (7) | 0.0205 (3) | |
H15' | 0.081078 | 0.123450 | 0.190146 | 0.025* | |
C16' | 0.07620 (15) | 0.28272 (15) | 0.18583 (7) | 0.0234 (3) | |
H16' | −0.006040 | 0.251404 | 0.150880 | 0.028* | |
C17' | 0.14437 (15) | 0.40440 (15) | 0.21284 (8) | 0.0242 (3) | |
H17' | 0.108590 | 0.456059 | 0.196406 | 0.029* | |
C18' | 0.26492 (15) | 0.45107 (13) | 0.26390 (7) | 0.0199 (3) | |
H18' | 0.312684 | 0.534651 | 0.281964 | 0.024* | |
N1' | 0.55003 (11) | 0.41385 (9) | 0.22932 (5) | 0.01266 (19) | |
N2' | 0.67301 (10) | 0.32232 (9) | 0.29374 (5) | 0.01215 (19) | |
N3' | 0.84368 (11) | 0.36751 (10) | 0.10580 (6) | 0.0146 (2) | |
N4' | 0.80664 (11) | 0.27784 (10) | 0.24374 (6) | 0.0154 (2) | |
H02' | 0.8068 (18) | 0.2361 (17) | 0.2788 (10) | 0.026 (5)* | |
H01' | 0.8381 (19) | 0.2724 (17) | 0.2073 (11) | 0.032 (5)* | |
N5' | 0.53703 (11) | 0.35582 (9) | 0.34781 (5) | 0.01244 (19) | |
O1' | 0.53653 (10) | 0.55695 (8) | 0.35774 (5) | 0.01774 (19) | |
O2' | 0.41688 (10) | 0.39421 (8) | 0.42515 (5) | 0.01618 (18) | |
O1W | 0.74945 (12) | 0.84359 (11) | 0.54810 (6) | 0.0277 (2) | |
H03 | 0.721 (2) | 0.779 (2) | 0.5641 (12) | 0.043 (6)* | |
H04 | 0.722 (3) | 0.881 (2) | 0.5691 (14) | 0.059 (7)* | |
K1 | 0.49406 (3) | 0.68951 (3) | 0.45040 (2) | 0.01683 (6) | |
K2 | 0.61675 (3) | 0.18387 (2) | 0.41184 (2) | 0.01349 (6) | |
C91 | 0.80325 (13) | 0.04442 (12) | 0.39544 (7) | 0.0162 (2) | |
H91 | 0.767210 | 0.011982 | 0.435682 | 0.019* | |
C92 | 0.90128 (15) | −0.08901 (13) | 0.40894 (8) | 0.0220 (3) | |
H92A | 0.859007 | −0.110674 | 0.449887 | 0.033* | |
H92B | 0.996418 | −0.057876 | 0.427120 | 0.033* | |
H92C | 0.864741 | −0.160831 | 0.373445 | 0.033* | |
C93 | 0.93416 (16) | 0.04719 (14) | 0.31230 (8) | 0.0245 (3) | |
H93A | 0.914558 | 0.111216 | 0.294568 | 0.037* | |
H93B | 0.896673 | −0.019652 | 0.273044 | 0.037* | |
H93C | 1.029863 | 0.079505 | 0.327664 | 0.037* | |
N91 | 0.87702 (12) | 0.00353 (10) | 0.37388 (6) | 0.0171 (2) | |
O91 | 0.77808 (10) | 0.12169 (9) | 0.36692 (5) | 0.01859 (19) | |
C94 | 0.80107 (14) | 0.47812 (13) | 0.48372 (8) | 0.0227 (3) | |
H94 | 0.776435 | 0.467817 | 0.431813 | 0.027* | |
C95 | 0.96954 (19) | 0.68087 (16) | 0.47527 (10) | 0.0424 (5) | |
H95A | 0.931121 | 0.654844 | 0.422790 | 0.064* | |
H95B | 1.062670 | 0.701335 | 0.486721 | 0.064* | |
H95C | 0.962128 | 0.752100 | 0.488784 | 0.064* | |
C96 | 0.9427 (3) | 0.60669 (19) | 0.59444 (10) | 0.0733 (9) | |
H96A | 1.030708 | 0.614032 | 0.610117 | 0.110* | |
H96B | 0.880906 | 0.539661 | 0.615825 | 0.110* | |
H96C | 0.945776 | 0.682111 | 0.610803 | 0.110* | |
N92 | 0.89949 (12) | 0.58360 (10) | 0.51602 (6) | 0.0225 (2) | |
O92 | 0.73809 (10) | 0.39159 (9) | 0.51491 (5) | 0.0222 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02517 (18) | 0.01570 (14) | 0.01810 (14) | 0.01219 (13) | 0.01195 (12) | 0.00747 (11) |
S2 | 0.01847 (16) | 0.01588 (14) | 0.01479 (13) | 0.01093 (12) | 0.00581 (11) | 0.00621 (11) |
S3 | 0.01119 (14) | 0.01133 (12) | 0.01105 (12) | 0.00464 (11) | 0.00318 (10) | 0.00208 (9) |
C2 | 0.0127 (6) | 0.0121 (5) | 0.0126 (5) | 0.0052 (5) | 0.0028 (4) | 0.0032 (4) |
C3A | 0.0134 (6) | 0.0159 (5) | 0.0133 (5) | 0.0071 (5) | 0.0031 (4) | 0.0019 (4) |
C4 | 0.0214 (7) | 0.0201 (6) | 0.0193 (6) | 0.0118 (5) | 0.0074 (5) | 0.0033 (5) |
C5 | 0.0201 (7) | 0.0250 (7) | 0.0181 (6) | 0.0121 (6) | 0.0065 (5) | 0.0004 (5) |
C6 | 0.0167 (7) | 0.0280 (7) | 0.0141 (6) | 0.0096 (6) | 0.0050 (5) | 0.0032 (5) |
C7 | 0.0198 (7) | 0.0219 (6) | 0.0156 (6) | 0.0095 (5) | 0.0065 (5) | 0.0057 (5) |
C7A | 0.0155 (6) | 0.0171 (6) | 0.0133 (5) | 0.0083 (5) | 0.0046 (4) | 0.0026 (4) |
C8 | 0.0133 (6) | 0.0112 (5) | 0.0120 (5) | 0.0055 (5) | 0.0041 (4) | 0.0030 (4) |
C9 | 0.0115 (6) | 0.0110 (5) | 0.0126 (5) | 0.0047 (4) | 0.0023 (4) | 0.0029 (4) |
C10 | 0.0101 (6) | 0.0125 (5) | 0.0123 (5) | 0.0040 (5) | 0.0023 (4) | 0.0024 (4) |
C11 | 0.0114 (6) | 0.0118 (5) | 0.0129 (5) | 0.0047 (5) | 0.0019 (4) | 0.0024 (4) |
C12 | 0.0183 (7) | 0.0189 (6) | 0.0180 (6) | 0.0120 (5) | 0.0038 (5) | 0.0028 (5) |
C13 | 0.0117 (6) | 0.0146 (5) | 0.0124 (5) | 0.0048 (5) | 0.0040 (4) | 0.0013 (4) |
C14 | 0.0213 (7) | 0.0154 (6) | 0.0223 (6) | 0.0057 (5) | 0.0015 (5) | 0.0037 (5) |
C15 | 0.0230 (8) | 0.0161 (6) | 0.0260 (7) | 0.0008 (6) | 0.0017 (6) | 0.0003 (5) |
C16 | 0.0143 (7) | 0.0268 (7) | 0.0191 (6) | 0.0036 (6) | 0.0009 (5) | −0.0039 (5) |
C17 | 0.0184 (7) | 0.0274 (7) | 0.0200 (6) | 0.0130 (6) | −0.0002 (5) | −0.0008 (5) |
C18 | 0.0165 (7) | 0.0176 (6) | 0.0184 (6) | 0.0095 (5) | 0.0030 (5) | 0.0005 (5) |
N1 | 0.0135 (5) | 0.0141 (5) | 0.0130 (5) | 0.0072 (4) | 0.0040 (4) | 0.0038 (4) |
N2 | 0.0143 (5) | 0.0143 (5) | 0.0137 (5) | 0.0076 (4) | 0.0047 (4) | 0.0039 (4) |
N3 | 0.0169 (6) | 0.0157 (5) | 0.0143 (5) | 0.0088 (4) | 0.0061 (4) | 0.0036 (4) |
N4 | 0.0261 (7) | 0.0183 (5) | 0.0174 (5) | 0.0154 (5) | 0.0109 (5) | 0.0087 (4) |
N5 | 0.0133 (5) | 0.0166 (5) | 0.0131 (5) | 0.0082 (4) | 0.0046 (4) | 0.0041 (4) |
O1 | 0.0151 (5) | 0.0109 (4) | 0.0176 (4) | 0.0043 (3) | 0.0039 (3) | 0.0015 (3) |
O2 | 0.0170 (5) | 0.0183 (4) | 0.0124 (4) | 0.0081 (4) | 0.0059 (3) | 0.0033 (3) |
S1' | 0.01307 (16) | 0.02409 (16) | 0.01137 (13) | 0.00726 (13) | 0.00081 (11) | −0.00157 (11) |
S2' | 0.02224 (17) | 0.02347 (15) | 0.01330 (14) | 0.01611 (14) | 0.00615 (12) | 0.00867 (11) |
S3' | 0.01608 (15) | 0.01188 (13) | 0.01004 (12) | 0.00854 (11) | 0.00399 (10) | 0.00284 (9) |
C2' | 0.0135 (6) | 0.0116 (5) | 0.0099 (5) | 0.0053 (5) | 0.0016 (4) | 0.0022 (4) |
C3A' | 0.0174 (6) | 0.0149 (5) | 0.0126 (5) | 0.0084 (5) | 0.0047 (5) | 0.0037 (4) |
C4' | 0.0193 (7) | 0.0250 (6) | 0.0171 (6) | 0.0127 (6) | 0.0060 (5) | 0.0054 (5) |
C5' | 0.0249 (8) | 0.0252 (7) | 0.0207 (6) | 0.0156 (6) | 0.0122 (5) | 0.0075 (5) |
C6' | 0.0290 (8) | 0.0218 (6) | 0.0150 (6) | 0.0131 (6) | 0.0093 (5) | 0.0030 (5) |
C7' | 0.0224 (7) | 0.0214 (6) | 0.0128 (6) | 0.0088 (6) | 0.0031 (5) | −0.0011 (5) |
C7A' | 0.0165 (6) | 0.0141 (5) | 0.0139 (5) | 0.0065 (5) | 0.0045 (5) | 0.0009 (4) |
C8' | 0.0105 (6) | 0.0116 (5) | 0.0108 (5) | 0.0042 (4) | 0.0020 (4) | 0.0021 (4) |
C9' | 0.0119 (6) | 0.0099 (5) | 0.0121 (5) | 0.0042 (4) | 0.0016 (4) | 0.0030 (4) |
C10' | 0.0113 (6) | 0.0096 (5) | 0.0118 (5) | 0.0043 (4) | 0.0014 (4) | 0.0013 (4) |
C11' | 0.0102 (6) | 0.0112 (5) | 0.0118 (5) | 0.0041 (4) | 0.0011 (4) | 0.0008 (4) |
C12' | 0.0236 (7) | 0.0284 (7) | 0.0179 (6) | 0.0194 (6) | 0.0041 (5) | 0.0058 (5) |
C13' | 0.0161 (6) | 0.0213 (6) | 0.0110 (5) | 0.0123 (5) | 0.0053 (4) | 0.0039 (4) |
C14' | 0.0164 (7) | 0.0211 (6) | 0.0141 (5) | 0.0102 (5) | 0.0058 (5) | 0.0030 (5) |
C15' | 0.0165 (7) | 0.0272 (7) | 0.0152 (6) | 0.0075 (6) | 0.0064 (5) | 0.0014 (5) |
C16' | 0.0161 (7) | 0.0421 (8) | 0.0150 (6) | 0.0159 (6) | 0.0048 (5) | 0.0061 (5) |
C17' | 0.0267 (8) | 0.0400 (8) | 0.0186 (6) | 0.0256 (7) | 0.0069 (5) | 0.0092 (6) |
C18' | 0.0254 (8) | 0.0259 (7) | 0.0161 (6) | 0.0185 (6) | 0.0055 (5) | 0.0043 (5) |
N1' | 0.0136 (5) | 0.0137 (5) | 0.0117 (4) | 0.0074 (4) | 0.0031 (4) | 0.0035 (4) |
N2' | 0.0122 (5) | 0.0135 (5) | 0.0112 (4) | 0.0069 (4) | 0.0019 (4) | 0.0022 (4) |
N3' | 0.0145 (5) | 0.0179 (5) | 0.0118 (5) | 0.0080 (4) | 0.0039 (4) | 0.0034 (4) |
N4' | 0.0169 (6) | 0.0217 (5) | 0.0126 (5) | 0.0131 (5) | 0.0042 (4) | 0.0048 (4) |
N5' | 0.0154 (5) | 0.0140 (5) | 0.0114 (4) | 0.0097 (4) | 0.0035 (4) | 0.0035 (4) |
O1' | 0.0255 (5) | 0.0119 (4) | 0.0171 (4) | 0.0094 (4) | 0.0065 (4) | 0.0032 (3) |
O2' | 0.0212 (5) | 0.0196 (4) | 0.0117 (4) | 0.0118 (4) | 0.0067 (3) | 0.0040 (3) |
O1W | 0.0339 (7) | 0.0209 (5) | 0.0306 (6) | 0.0110 (5) | 0.0177 (5) | 0.0049 (4) |
K1 | 0.02118 (15) | 0.01917 (13) | 0.01416 (12) | 0.01203 (11) | 0.00636 (10) | 0.00500 (9) |
K2 | 0.01341 (13) | 0.01430 (12) | 0.01346 (11) | 0.00694 (10) | 0.00394 (9) | 0.00372 (9) |
C91 | 0.0155 (6) | 0.0176 (6) | 0.0155 (5) | 0.0076 (5) | 0.0047 (5) | 0.0019 (4) |
C92 | 0.0273 (8) | 0.0219 (6) | 0.0239 (7) | 0.0167 (6) | 0.0081 (6) | 0.0079 (5) |
C93 | 0.0295 (8) | 0.0312 (7) | 0.0257 (7) | 0.0208 (7) | 0.0165 (6) | 0.0128 (6) |
N91 | 0.0193 (6) | 0.0188 (5) | 0.0182 (5) | 0.0118 (5) | 0.0077 (4) | 0.0064 (4) |
O91 | 0.0206 (5) | 0.0208 (5) | 0.0190 (4) | 0.0130 (4) | 0.0062 (4) | 0.0039 (4) |
C94 | 0.0196 (7) | 0.0230 (7) | 0.0179 (6) | 0.0054 (6) | 0.0012 (5) | 0.0036 (5) |
C95 | 0.0359 (10) | 0.0305 (9) | 0.0324 (9) | −0.0041 (8) | 0.0014 (7) | 0.0163 (7) |
C96 | 0.097 (2) | 0.0295 (9) | 0.0224 (9) | −0.0215 (11) | 0.0030 (10) | −0.0015 (7) |
N92 | 0.0224 (6) | 0.0163 (5) | 0.0193 (5) | 0.0029 (5) | 0.0023 (5) | 0.0050 (4) |
O92 | 0.0209 (5) | 0.0163 (4) | 0.0219 (5) | 0.0036 (4) | 0.0037 (4) | 0.0033 (4) |
S1—C7A | 1.7299 (13) | S3'—N5' | 1.5672 (10) |
S1—C2 | 1.7716 (12) | S3'—C13' | 1.7778 (13) |
S2—C9 | 1.7600 (12) | C2'—N3' | 1.3058 (17) |
S2—C12 | 1.7957 (13) | C2'—C8' | 1.4685 (16) |
S3—O2 | 1.4500 (9) | C3A'—N3' | 1.3915 (15) |
S3—O1 | 1.4611 (9) | C3A'—C4' | 1.3986 (19) |
S3—N5 | 1.5770 (11) | C3A'—C7A' | 1.4046 (18) |
S3—C13 | 1.7767 (13) | C4'—C5' | 1.3843 (18) |
C2—N3 | 1.3126 (16) | C4'—H4' | 0.9500 |
C2—C8 | 1.4575 (16) | C5'—C6' | 1.401 (2) |
C3A—N3 | 1.3859 (16) | C5'—H5' | 0.9500 |
C3A—C7A | 1.4008 (17) | C6'—C7' | 1.379 (2) |
C3A—C4 | 1.4020 (18) | C6'—H6' | 0.9500 |
C4—C5 | 1.3822 (19) | C7'—C7A' | 1.3964 (17) |
C4—H4 | 0.9500 | C7'—H7' | 0.9500 |
C5—C6 | 1.403 (2) | C8'—C9' | 1.4024 (17) |
C5—H5 | 0.9500 | C8'—C11' | 1.4256 (16) |
C6—C7 | 1.3818 (19) | C9'—N1' | 1.3360 (15) |
C6—H6 | 0.9500 | C10'—N2' | 1.3432 (15) |
C7—C7A | 1.3966 (17) | C10'—N1' | 1.3519 (15) |
C7—H7 | 0.9500 | C10'—N5' | 1.3708 (15) |
C8—C9 | 1.4100 (17) | C11'—N2' | 1.3451 (15) |
C8—C11 | 1.4354 (16) | C11'—N4' | 1.3462 (16) |
C9—N1 | 1.3346 (15) | C12'—H12D | 0.9800 |
C10—N2 | 1.3419 (16) | C12'—H12E | 0.9800 |
C10—N1 | 1.3507 (15) | C12'—H12F | 0.9800 |
C10—N5 | 1.3726 (15) | C13'—C14' | 1.3877 (18) |
C11—N4 | 1.3454 (16) | C13'—C18' | 1.3929 (17) |
C11—N2 | 1.3474 (15) | C14'—C15' | 1.3893 (19) |
C12—H12A | 0.9800 | C14'—H14' | 0.9500 |
C12—H12B | 0.9800 | C15'—C16' | 1.387 (2) |
C12—H12C | 0.9800 | C15'—H15' | 0.9500 |
C13—C18 | 1.3877 (17) | C16'—C17' | 1.386 (2) |
C13—C14 | 1.3943 (18) | C16'—H16' | 0.9500 |
C14—C15 | 1.393 (2) | C17'—C18' | 1.390 (2) |
C14—H14 | 0.9500 | C17'—H17' | 0.9500 |
C15—C16 | 1.390 (2) | C18'—H18' | 0.9500 |
C15—H15 | 0.9500 | N4'—H02' | 0.847 (19) |
C16—C17 | 1.385 (2) | N4'—H01' | 0.87 (2) |
C16—H16 | 0.9500 | O1W—H03 | 0.81 (2) |
C17—C18 | 1.3938 (19) | O1W—H04 | 0.82 (3) |
C17—H17 | 0.9500 | C91—O91 | 1.2380 (15) |
C18—H18 | 0.9500 | C91—N91 | 1.3291 (17) |
K1—N2 | 2.8371 (10) | C91—H91 | 0.9500 |
K1—N5 | 2.9038 (11) | C92—N91 | 1.4548 (16) |
K1—O1' | 2.6918 (9) | C92—H92A | 0.9800 |
K1—O2'i | 2.7811 (9) | C92—H92B | 0.9800 |
K1—O1W | 2.8991 (13) | C92—H92C | 0.9800 |
K1—O92i | 2.6779 (11) | C93—N91 | 1.4497 (17) |
K2—N2' | 2.8320 (10) | C93—H93A | 0.9800 |
K2—N5' | 2.9133 (10) | C93—H93B | 0.9800 |
K2—O1ii | 2.6846 (10) | C93—H93C | 0.9800 |
K2—O2i | 2.6782 (9) | C94—O92 | 1.2333 (17) |
K2—O91 | 2.6594 (10) | C94—N92 | 1.3177 (18) |
K2—O92 | 2.8193 (10) | C94—H94 | 0.9500 |
N4—H02 | 0.87 (2) | C95—N92 | 1.4516 (19) |
N4—H01 | 0.85 (2) | C95—H95A | 0.9800 |
S1'—C7A' | 1.7299 (13) | C95—H95B | 0.9800 |
S1'—C2' | 1.7612 (12) | C95—H95C | 0.9800 |
S2'—C9' | 1.7639 (12) | C96—N92 | 1.439 (2) |
S2'—C12' | 1.8002 (14) | C96—H96A | 0.9800 |
S3'—O1' | 1.4541 (9) | C96—H96B | 0.9800 |
S3'—O2' | 1.4566 (9) | C96—H96C | 0.9800 |
C7A—S1—C2 | 89.78 (6) | N2'—C11'—N4' | 115.39 (10) |
C9—S2—C12 | 100.78 (6) | N2'—C11'—C8' | 121.93 (11) |
O2—S3—O1 | 113.35 (5) | N4'—C11'—C8' | 122.68 (11) |
O2—S3—N5 | 106.98 (5) | S2'—C12'—H12D | 109.5 |
O1—S3—N5 | 116.05 (6) | S2'—C12'—H12E | 109.5 |
O2—S3—C13 | 106.02 (6) | H12D—C12'—H12E | 109.5 |
O1—S3—C13 | 106.14 (6) | S2'—C12'—H12F | 109.5 |
N5—S3—C13 | 107.73 (6) | H12D—C12'—H12F | 109.5 |
N3—C2—C8 | 122.89 (11) | H12E—C12'—H12F | 109.5 |
N3—C2—S1 | 113.58 (9) | C14'—C13'—C18' | 121.11 (12) |
C8—C2—S1 | 123.50 (9) | C14'—C13'—S3' | 118.40 (9) |
N3—C3A—C7A | 114.97 (11) | C18'—C13'—S3' | 120.36 (10) |
N3—C3A—C4 | 125.16 (11) | C13'—C14'—C15' | 119.30 (12) |
C7A—C3A—C4 | 119.86 (12) | C13'—C14'—H14' | 120.3 |
C5—C4—C3A | 118.46 (12) | C15'—C14'—H14' | 120.3 |
C5—C4—H4 | 120.8 | C16'—C15'—C14' | 120.01 (13) |
C3A—C4—H4 | 120.8 | C16'—C15'—H15' | 120.0 |
C4—C5—C6 | 120.89 (13) | C14'—C15'—H15' | 120.0 |
C4—C5—H5 | 119.6 | C17'—C16'—C15' | 120.38 (13) |
C6—C5—H5 | 119.6 | C17'—C16'—H16' | 119.8 |
C7—C6—C5 | 121.59 (12) | C15'—C16'—H16' | 119.8 |
C7—C6—H6 | 119.2 | C16'—C17'—C18' | 120.21 (13) |
C5—C6—H6 | 119.2 | C16'—C17'—H17' | 119.9 |
C6—C7—C7A | 117.32 (12) | C18'—C17'—H17' | 119.9 |
C6—C7—H7 | 121.3 | C17'—C18'—C13' | 118.96 (13) |
C7A—C7—H7 | 121.3 | C17'—C18'—H18' | 120.5 |
C7—C7A—C3A | 121.87 (12) | C13'—C18'—H18' | 120.5 |
C7—C7A—S1 | 128.54 (10) | C9'—N1'—C10' | 116.17 (10) |
C3A—C7A—S1 | 109.57 (9) | C10'—N2'—C11' | 117.31 (10) |
C9—C8—C11 | 113.91 (11) | C10'—N2'—K2 | 101.07 (7) |
C9—C8—C2 | 125.26 (10) | C11'—N2'—K2 | 136.87 (8) |
C11—C8—C2 | 120.71 (11) | C2'—N3'—C3A' | 111.15 (10) |
N1—C9—C8 | 124.03 (11) | C11'—N4'—H02' | 116.1 (13) |
N1—C9—S2 | 115.19 (9) | C11'—N4'—H01' | 119.3 (13) |
C8—C9—S2 | 120.71 (9) | H02'—N4'—H01' | 121.2 (18) |
N2—C10—N1 | 125.23 (11) | C10'—N5'—S3' | 120.32 (8) |
N2—C10—N5 | 113.88 (10) | C10'—N5'—K2 | 96.61 (7) |
N1—C10—N5 | 120.89 (11) | S3'—N5'—K2 | 143.06 (5) |
N4—C11—N2 | 115.53 (11) | S3'—O1'—K1 | 114.51 (5) |
N4—C11—C8 | 122.42 (11) | K1—O1W—H03 | 74.2 (16) |
N2—C11—C8 | 122.05 (11) | K1—O1W—H04 | 93.9 (18) |
S2—C12—H12A | 109.5 | H03—O1W—H04 | 103 (2) |
S2—C12—H12B | 109.5 | O92i—K1—O1' | 122.10 (3) |
H12A—C12—H12B | 109.5 | O92i—K1—O2'i | 89.19 (3) |
S2—C12—H12C | 109.5 | O1'—K1—O2'i | 94.53 (3) |
H12A—C12—H12C | 109.5 | O92i—K1—N2 | 117.13 (3) |
H12B—C12—H12C | 109.5 | O1'—K1—N2 | 72.98 (3) |
C18—C13—C14 | 120.90 (12) | O2'i—K1—N2 | 153.65 (3) |
C18—C13—S3 | 120.94 (10) | O92i—K1—O1W | 125.24 (3) |
C14—C13—S3 | 118.07 (10) | O1'—K1—O1W | 105.49 (3) |
C15—C14—C13 | 119.14 (13) | O2'i—K1—O1W | 59.75 (3) |
C15—C14—H14 | 120.4 | N2—K1—O1W | 100.51 (3) |
C13—C14—H14 | 120.4 | O92i—K1—N5 | 80.48 (3) |
C16—C15—C14 | 120.15 (13) | O1'—K1—N5 | 116.98 (3) |
C16—C15—H15 | 119.9 | O2'i—K1—N5 | 147.63 (3) |
C14—C15—H15 | 119.9 | N2—K1—N5 | 46.67 (3) |
C17—C16—C15 | 120.28 (13) | O1W—K1—N5 | 101.98 (3) |
C17—C16—H16 | 119.9 | O91—K2—O2i | 79.15 (3) |
C15—C16—H16 | 119.9 | O91—K2—O1ii | 122.24 (3) |
C16—C17—C18 | 120.15 (13) | O2i—K2—O1ii | 104.71 (3) |
C16—C17—H17 | 119.9 | O91—K2—O92 | 116.05 (3) |
C18—C17—H17 | 119.9 | O2i—K2—O92 | 74.59 (3) |
C13—C18—C17 | 119.37 (12) | O1ii—K2—O92 | 120.48 (3) |
C13—C18—H18 | 120.3 | O91—K2—N2' | 78.44 (3) |
C17—C18—H18 | 120.3 | O2i—K2—N2' | 145.92 (3) |
C9—N1—C10 | 116.76 (10) | O1ii—K2—N2' | 108.90 (3) |
C10—N2—C11 | 117.63 (10) | O92—K2—N2' | 92.77 (3) |
C10—N2—K1 | 101.67 (7) | O91—K2—N5' | 124.93 (3) |
C11—N2—K1 | 140.70 (8) | O2i—K2—N5' | 145.82 (3) |
C2—N3—C3A | 112.08 (10) | O1ii—K2—N5' | 83.45 (3) |
C11—N4—H02 | 116.3 (13) | O92—K2—N5' | 72.82 (3) |
C11—N4—H01 | 116.8 (13) | N2'—K2—N5' | 46.50 (3) |
H02—N4—H01 | 122.6 (18) | O91—C91—N91 | 124.77 (12) |
C10—N5—S3 | 121.03 (9) | O91—C91—H91 | 117.6 |
C10—N5—K1 | 97.74 (7) | N91—C91—H91 | 117.6 |
S3—N5—K1 | 137.67 (6) | N91—C92—H92A | 109.5 |
S3—O1—K2iii | 115.26 (5) | N91—C92—H92B | 109.5 |
S3—O2—K2i | 136.13 (5) | H92A—C92—H92B | 109.5 |
C7A'—S1'—C2' | 89.38 (6) | N91—C92—H92C | 109.5 |
C9'—S2'—C12' | 101.82 (6) | H92A—C92—H92C | 109.5 |
O1'—S3'—O2' | 113.04 (5) | H92B—C92—H92C | 109.5 |
O1'—S3'—N5' | 114.63 (6) | N91—C93—H93A | 109.5 |
O2'—S3'—N5' | 107.06 (5) | N91—C93—H93B | 109.5 |
O1'—S3'—C13' | 107.07 (6) | H93A—C93—H93B | 109.5 |
O2'—S3'—C13' | 104.46 (6) | N91—C93—H93C | 109.5 |
N5'—S3'—C13' | 110.11 (6) | H93A—C93—H93C | 109.5 |
N3'—C2'—C8' | 123.71 (11) | H93B—C93—H93C | 109.5 |
N3'—C2'—S1' | 114.91 (9) | C91—N91—C93 | 121.04 (11) |
C8'—C2'—S1' | 121.23 (9) | C91—N91—C92 | 122.18 (11) |
N3'—C3A'—C4' | 125.82 (12) | C93—N91—C92 | 116.75 (11) |
N3'—C3A'—C7A' | 114.92 (11) | C91—O91—K2 | 120.87 (8) |
C4'—C3A'—C7A' | 119.19 (11) | O92—C94—N92 | 125.77 (13) |
C5'—C4'—C3A' | 119.11 (13) | O92—C94—K2 | 52.85 (7) |
C5'—C4'—H4' | 120.4 | N92—C94—K2 | 163.54 (11) |
C3A'—C4'—H4' | 120.4 | O92—C94—H94 | 117.1 |
C4'—C5'—C6' | 121.01 (13) | N92—C94—H94 | 117.1 |
C4'—C5'—H5' | 119.5 | K2—C94—H94 | 67.1 |
C6'—C5'—H5' | 119.5 | N92—C95—H95A | 109.5 |
C7'—C6'—C5' | 120.77 (12) | N92—C95—H95B | 109.5 |
C7'—C6'—H6' | 119.6 | H95A—C95—H95B | 109.5 |
C5'—C6'—H6' | 119.6 | N92—C95—H95C | 109.5 |
C6'—C7'—C7A' | 118.25 (13) | H95A—C95—H95C | 109.5 |
C6'—C7'—H7' | 120.9 | H95B—C95—H95C | 109.5 |
C7A'—C7'—H7' | 120.9 | N92—C96—H96A | 109.5 |
C7'—C7A'—C3A' | 121.65 (12) | N92—C96—H96B | 109.5 |
C7'—C7A'—S1' | 128.70 (11) | H96A—C96—H96B | 109.5 |
C3A'—C7A'—S1' | 109.58 (9) | N92—C96—H96C | 109.5 |
C9'—C8'—C11' | 114.77 (11) | H96A—C96—H96C | 109.5 |
C9'—C8'—C2' | 124.58 (10) | H96B—C96—H96C | 109.5 |
C11'—C8'—C2' | 120.62 (11) | C94—N92—C96 | 120.61 (13) |
N1'—C9'—C8' | 123.92 (11) | C94—N92—C95 | 122.44 (13) |
N1'—C9'—S2' | 116.05 (9) | C96—N92—C95 | 116.95 (14) |
C8'—C9'—S2' | 120.02 (9) | C94—O92—K1i | 132.77 (10) |
N2'—C10'—N1' | 125.70 (11) | C94—O92—K2 | 106.74 (9) |
N2'—C10'—N5' | 113.44 (10) | K1i—O92—K2 | 87.35 (3) |
N1'—C10'—N5' | 120.83 (11) | ||
C7A—S1—C2—N3 | −0.17 (11) | C3A'—C4'—C5'—C6' | 1.0 (2) |
C7A—S1—C2—C8 | 177.68 (11) | C4'—C5'—C6'—C7' | 0.1 (2) |
N3—C3A—C4—C5 | 179.77 (13) | C5'—C6'—C7'—C7A' | −1.4 (2) |
C7A—C3A—C4—C5 | 0.8 (2) | C6'—C7'—C7A'—C3A' | 1.59 (19) |
C3A—C4—C5—C6 | −0.1 (2) | C6'—C7'—C7A'—S1' | 178.38 (11) |
C4—C5—C6—C7 | −0.8 (2) | N3'—C3A'—C7A'—C7' | 176.71 (12) |
C5—C6—C7—C7A | 1.1 (2) | C4'—C3A'—C7A'—C7' | −0.55 (19) |
C6—C7—C7A—C3A | −0.3 (2) | N3'—C3A'—C7A'—S1' | −0.63 (14) |
C6—C7—C7A—S1 | −178.52 (11) | C4'—C3A'—C7A'—S1' | −177.89 (10) |
N3—C3A—C7A—C7 | −179.64 (12) | C2'—S1'—C7A'—C7' | −175.59 (13) |
C4—C3A—C7A—C7 | −0.6 (2) | C2'—S1'—C7A'—C3A' | 1.51 (9) |
N3—C3A—C7A—S1 | −1.16 (14) | N3'—C2'—C8'—C9' | 142.01 (13) |
C4—C3A—C7A—S1 | 177.90 (11) | S1'—C2'—C8'—C9' | −42.51 (16) |
C2—S1—C7A—C7 | 179.08 (13) | N3'—C2'—C8'—C11' | −40.08 (17) |
C2—S1—C7A—C3A | 0.73 (10) | S1'—C2'—C8'—C11' | 135.40 (10) |
N3—C2—C8—C9 | −160.28 (13) | C11'—C8'—C9'—N1' | −1.83 (17) |
S1—C2—C8—C9 | 22.06 (18) | C2'—C8'—C9'—N1' | 176.19 (11) |
N3—C2—C8—C11 | 15.40 (19) | C11'—C8'—C9'—S2' | 176.82 (9) |
S1—C2—C8—C11 | −162.25 (10) | C2'—C8'—C9'—S2' | −5.15 (17) |
C11—C8—C9—N1 | 4.82 (18) | C12'—S2'—C9'—N1' | −12.29 (11) |
C2—C8—C9—N1 | −179.23 (12) | C12'—S2'—C9'—C8' | 168.96 (10) |
C11—C8—C9—S2 | −171.83 (9) | C9'—C8'—C11'—N2' | 3.63 (17) |
C2—C8—C9—S2 | 4.12 (18) | C2'—C8'—C11'—N2' | −174.47 (11) |
C12—S2—C9—N1 | 1.16 (11) | C9'—C8'—C11'—N4' | −176.93 (11) |
C12—S2—C9—C8 | 178.09 (10) | C2'—C8'—C11'—N4' | 4.96 (18) |
C9—C8—C11—N4 | 174.05 (12) | O1'—S3'—C13'—C14' | 159.94 (10) |
C2—C8—C11—N4 | −2.09 (19) | O2'—S3'—C13'—C14' | −79.93 (11) |
C9—C8—C11—N2 | −6.32 (17) | N5'—S3'—C13'—C14' | 34.72 (12) |
C2—C8—C11—N2 | 177.53 (11) | O1'—S3'—C13'—C18' | −24.15 (12) |
O2—S3—C13—C18 | 113.30 (11) | O2'—S3'—C13'—C18' | 95.97 (11) |
O1—S3—C13—C18 | −7.52 (12) | N5'—S3'—C13'—C18' | −149.37 (10) |
N5—S3—C13—C18 | −132.44 (11) | C18'—C13'—C14'—C15' | 0.69 (19) |
O2—S3—C13—C14 | −63.18 (12) | S3'—C13'—C14'—C15' | 176.57 (10) |
O1—S3—C13—C14 | 175.99 (10) | C13'—C14'—C15'—C16' | −1.62 (19) |
N5—S3—C13—C14 | 51.07 (12) | C14'—C15'—C16'—C17' | 1.2 (2) |
C18—C13—C14—C15 | −0.6 (2) | C15'—C16'—C17'—C18' | 0.1 (2) |
S3—C13—C14—C15 | 175.93 (11) | C16'—C17'—C18'—C13' | −1.0 (2) |
C13—C14—C15—C16 | −0.4 (2) | C14'—C13'—C18'—C17' | 0.6 (2) |
C14—C15—C16—C17 | 1.1 (2) | S3'—C13'—C18'—C17' | −175.16 (10) |
C15—C16—C17—C18 | −1.0 (2) | C8'—C9'—N1'—C10' | −2.00 (18) |
C14—C13—C18—C17 | 0.7 (2) | S2'—C9'—N1'—C10' | 179.30 (9) |
S3—C13—C18—C17 | −175.65 (10) | N2'—C10'—N1'—C9' | 4.65 (18) |
C16—C17—C18—C13 | 0.0 (2) | N5'—C10'—N1'—C9' | −173.44 (11) |
C8—C9—N1—C10 | 0.33 (18) | N1'—C10'—N2'—C11' | −2.95 (18) |
S2—C9—N1—C10 | 177.15 (9) | N5'—C10'—N2'—C11' | 175.27 (10) |
N2—C10—N1—C9 | −4.84 (18) | N1'—C10'—N2'—K2 | −162.67 (10) |
N5—C10—N1—C9 | 175.93 (11) | N5'—C10'—N2'—K2 | 15.55 (11) |
N1—C10—N2—C11 | 3.35 (19) | N4'—C11'—N2'—C10' | 179.06 (11) |
N5—C10—N2—C11 | −177.38 (11) | C8'—C11'—N2'—C10' | −1.46 (17) |
N1—C10—N2—K1 | −177.35 (11) | N4'—C11'—N2'—K2 | −30.78 (17) |
N5—C10—N2—K1 | 1.93 (12) | C8'—C11'—N2'—K2 | 148.69 (9) |
N4—C11—N2—C10 | −177.73 (11) | C8'—C2'—N3'—C3A' | 178.01 (11) |
C8—C11—N2—C10 | 2.63 (18) | S1'—C2'—N3'—C3A' | 2.26 (13) |
N4—C11—N2—K1 | 3.35 (19) | C4'—C3A'—N3'—C2' | 176.01 (12) |
C8—C11—N2—K1 | −176.30 (9) | C7A'—C3A'—N3'—C2' | −1.04 (15) |
C8—C2—N3—C3A | −178.31 (11) | N2'—C10'—N5'—S3' | 166.36 (9) |
S1—C2—N3—C3A | −0.45 (14) | N1'—C10'—N5'—S3' | −15.33 (16) |
C7A—C3A—N3—C2 | 1.06 (16) | N2'—C10'—N5'—K2 | −14.92 (10) |
C4—C3A—N3—C2 | −177.94 (13) | N1'—C10'—N5'—K2 | 163.39 (10) |
N2—C10—N5—S3 | −164.13 (9) | O1'—S3'—N5'—C10' | −55.50 (11) |
N1—C10—N5—S3 | 15.18 (17) | O2'—S3'—N5'—C10' | 178.27 (9) |
N2—C10—N5—K1 | −1.86 (11) | C13'—S3'—N5'—C10' | 65.28 (11) |
N1—C10—N5—K1 | 177.45 (10) | O1'—S3'—N5'—K2 | 126.62 (9) |
O2—S3—N5—C10 | 176.11 (10) | O2'—S3'—N5'—K2 | 0.38 (11) |
O1—S3—N5—C10 | −56.26 (12) | C13'—S3'—N5'—K2 | −112.60 (9) |
C13—S3—N5—C10 | 62.49 (11) | O2'—S3'—O1'—K1 | −20.89 (7) |
O2—S3—N5—K1 | 22.74 (10) | N5'—S3'—O1'—K1 | −143.97 (5) |
O1—S3—N5—K1 | 150.37 (7) | C13'—S3'—O1'—K1 | 93.58 (6) |
C13—S3—N5—K1 | −90.88 (9) | O91—C91—N91—C93 | −0.8 (2) |
O2—S3—O1—K2iii | 99.65 (6) | O91—C91—N91—C92 | −178.96 (13) |
N5—S3—O1—K2iii | −24.76 (7) | N91—C91—O91—K2 | 176.30 (10) |
C13—S3—O1—K2iii | −144.38 (5) | O92—C94—N92—C96 | −0.2 (3) |
O1—S3—O2—K2i | −113.35 (8) | K2—C94—N92—C96 | −79.3 (4) |
N5—S3—O2—K2i | 15.85 (9) | O92—C94—N92—C95 | 179.47 (17) |
C13—S3—O2—K2i | 130.61 (7) | K2—C94—N92—C95 | 100.3 (4) |
C7A'—S1'—C2'—N3' | −2.26 (10) | N92—C94—O92—K1i | 98.16 (17) |
C7A'—S1'—C2'—C8' | −178.12 (10) | K2—C94—O92—K1i | −102.27 (11) |
N3'—C3A'—C4'—C5' | −177.66 (12) | N92—C94—O92—K2 | −159.57 (14) |
C7A'—C3A'—C4'—C5' | −0.73 (19) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) x, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H01···N3 | 0.85 (2) | 2.01 (2) | 2.6859 (15) | 136.0 (18) |
N4′—H01′···N3′ | 0.87 (2) | 2.26 (2) | 2.8781 (15) | 128.5 (16) |
N4—H02···O1′ | 0.87 (2) | 2.06 (2) | 2.9205 (14) | 167.5 (18) |
N4′—H02′···O91 | 0.847 (19) | 2.180 (19) | 3.0207 (14) | 172.0 (17) |
O1W—H03···O2′i | 0.81 (2) | 2.07 (2) | 2.8314 (15) | 157 (2) |
O1W—H04···O1iv | 0.82 (3) | 2.00 (3) | 2.8211 (15) | 176 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (iv) −x+1, −y+2, −z+1. |
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