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Crystal structure determination of rac-11′-(1-acetyl-1H-indazol-3-yl)-11′,11a′-di­hydro-10′H,17′H-spiro­[indene-2,18′-[5a,16b]methano­tri­indeno[1,2-b:1′,2′-d:2′′,1′′-g]oxocine]-1,3,10′,12′,17′(10aH)-penta­one aceto­nitrile 1.5-solvate

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry, Ben Gurion University of the Negev, POB 653, 8410501, Beer Sheva, Israel
*Correspondence e-mail: markbara@post.bgu.ac.il

Edited by O. Blacque, University of Zürich, Switzerland (Received 14 August 2018; accepted 20 August 2018; online 18 September 2018)

The title compound, C46H26N2O7·1.5CH3CN, is the aldol condensation product of bindone with indazole-3-carbaldehyde followed by double inter­molecular cyclization. The asymmetric unit, which has monoclinic P21/c symmetry, contains two independent mol­ecules of the title compound and three aceto­nitrile mol­ecules. The title mol­ecule comprises a central eight-membered ring, which contains an enol–ester, from which five arms extend. The arms exhibit inter­molecular inter­actions within the crystal lattice between mol­ecules of the title compound and with co-crystallized solvent mol­ecules (aceto­nitrile).

1. Chemical context

1,3-Indandione derivatives have been known for more than a century and have found numerous applications as drugs (anti­coagulants, analgesics, anti-inflammatory medicines; Eriks et al.,1979[Eriks, J. C., Van der Goot, H. & Nauta, W. T. (1979). Eur. J. Med. Chem. 14, 411-414.]), reagents in analytical and forensic chemistry (ninhydrins; Hansen & Joullié, 2005[Hansen, D. B. & Joullié, M. M. (2005). Chem. Soc. Rev. 34, 408-417.]), dyes and pigments (Manukian & Mangini, 1970[Manukian, B. K. & Mangini, A. (1970). Chimia, 24, 328-338.]; Schelz, 1975[Schelz, D. (1975). Helv. Chim. Acta, 58, 1207-1217.]; Bello et al., 1987[Bello, K. A., Cheng, L. & Griffiths, J. (1987). J. Chem. Soc. Perkin Trans. 2, pp. 815-818.]), semiconductors and photo semiconductors (Silinsh & Taure, 1969[Silinsh, E. A. & Taure, L. (1969). Phys. Stat. Sol. (b), 32, 847-852.]), and components of advanced materials (Gvishi et al., 2003[Gvishi, R., Berkovic, G., Kotler, Z., Krief, P., Becker, J. Y., Sigalov, M., Shapiro, L. & Khodorkovsky, V. (2003). Proc. SPIE, 5036, 437-442.]; Acharya et al., 2005[Acharya, S., Krief, P., Khodorkovsky, V., Kotler, Z., Berkovic, G., Klug, J. T. & Efrima, S. (2005). New J. Chem. 29, 1049-1057.]; Lokshin et al., 2017[Lokshin, V., Bekere, L. & Khodorkovsky, V. (2017). Dyes Pigments, 145, 570-575.]). One of the important features of 1,3-indandione as well as its dimer bindone [2-(2,3-di­hydro-3-oxo-1H-inden-1-yl­idene)-1H-indene-1, 3(2H)-dione] is the ease of their self-condensation, often with the formation of complex cyclic structures (Jacob et al., 2000[Jacob, K., Sigalov, M., Becker, J. Y., Ellern, A. & Khodorkovsky, V. (2000). Eur. J. Org. Chem. pp. 2047-2055.]). For over a century, cyclic 1,3-diketones have been known to form condensation products, including self-condensation (Wislicenus, 1887[Wislicenus, W. (1887). Ber. Dtsch. Chem. Ges. 20, 589-595.]). As a result of this property, they have found use as inter­mediates for condensed cyclization products (Sekhar, 2004[Sekhar, B. C. (2004). J. Heterocycl. Chem. 41, 807-855.]; Kozlov & Gusak, 2006[Kozlov, N. G. & Gusak, K. N. (2006). Zh. Org. Chim. 42, 1680-1686.]) that have themselves found use as anti­emetic (Kuang et al., 1994[Kuang, Y., Zhang, S. & Sun, X. (1994). Zhongguo Yiyao Gongye Zazhi, 25, 36.]) and anti­cancer (Heidelberger & Ansfield, 1963[Heidelberger, C. & Ansfield, F. J. (1963). Cancer Res. 23, 1226-1243.]) drugs.

[Scheme 1]

2. Structural commentary

The asymmetric unit of the title compound, shown in Fig. 1[link], contains two independent mol­ecules and three co-crystallized aceto­nitrile mol­ecules (Z = 8, Z′ = 4). The title compound is shown in Fig. 2[link].

[Figure 1]
Figure 1
ORTEP representation of the asymmetric unit of the crystal, containing two compound mol­ecules and three co-crystallized aceto­nitrile mol­ecules. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
View of one of the independent mol­ecules in the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

The core of the mol­ecule represented by an eight-membered oxocine ring, which is linked in the center by a carbon atom, C1 bridging between C2 and C6, and includes an ether group as shown in Fig. 3[link]a. Bond lengths, listed in Table 1[link], clearly indicate the presence of a C=C double bond with a bond length of 1.357 (3) Å and also featuring a short C—C bond with a bond length of 1.494 (3) Å,. Also inter­esting to note is the stark difference between the C—O bond lengths within the ring, ranging from 1.333 (3) to 1.462 (2) Å. The presence of the double bond, the short C—C bond and the great variation within the C—O bonds is due to the five arms of the structure, which extend from the central ring as shown in Fig. 3[link]b–3f and are described in Table 2[link].

Table 1
Bond lengths (Å) in the central eight-membered ring of the mol­ecule

Atom pair Bond length Atom pair Bond length
C1—C2 1.547 (3) C5—C6 1.554 (3)
C1—C6 1.576 (3) C6—C7 1.494 (3)
C2—C3 1.552 (3) C7=C8 1.357 (3)
C3—C4 1.546 (3) O1—C8 1.332 (3)
C4—C5 1.544 (3) O1—C2 1.462 (2)

Table 2
The various arms extending from the central ring

Arm designation Carbon atoms shared with central ring IUPAC name
1 (Fig. 3[link]b) C5, C6 1-indanone
2 (Fig. 3[link]c) C2, C3 1-indanone
3 (Fig. 3[link]d) C1 1,3-indandione
4 (Fig. 3[link]e) C4 1-(1H-indazol-1-yl)ethanone
5 (Fig. 3[link]f) C7, C8 1-H-inden-1-one
[Figure 3]
Figure 3
(a) The central eight-membered ring of the compound with the bridging carbon atom between C2 and C6. (b)–(f) The various arms extending from the central ring, showing the connection to the central ring.

3. Supra­molecular features

The packing of the crystal structure indicates that the aceto­nitrile mol­ecules inter­act with up to three different aromatic π systems belonging to arms 1–3; these inter­actions can be seen in Fig. 4[link]a. The inter­actions between aceto­nitrile and arms 2 and 3 also force some rigidity upon the structure, as seen in Fig. 4[link]b. It is worth noting that the inter­action seen in Fig. 4[link]b is not observed in the asymmetric unit, but in the extended packing of the crystal. These inter­actions are listed in Table 3[link].

Table 3
Packing inter­actions found inside the crystal lattice (Å)

Shortest bond distances that were found are shown for the various inter­actions.

Inter­action C⋯C
C12 (Arm 1)⋯C97i (Aceto­nitrile) 3.489 (3)
C26 (Arm 3)⋯C97i (Aceto­nitrile) 3.475 (3)
C58 (Arm 2′)⋯C97ii (Aceto­nitrile) 3.317 (3)
C66 (Arm 1)⋯C66i (Arm 1′) 3.388 (2)
C32 (Arm 4)⋯C89iv (Arm 2′) 3.381 (3)
Symmetry codes: (i) 1 − x, 2 − y, 1 − z; (ii) x − 1, y, z; (iii) x, [{3\over 2}] − y, −[{1\over 2}] + z.
[Figure 4]
Figure 4
(a) van der Waals inter­actions between the aceto­nitrile mol­ecules and the title compound: one aceto­nitrile mol­ecule inter­acts with up to three arms. (b) Illustration of the rigidity that is enforced upon two arms of the title compound as a result of van der Waals inter­actions.

A second inter­action, which contributes to the crystal packing, is a ππ inter­action between arms 4 and 5, as seen in Fig. 5[link]a. A third inter­action, which contributes to the crystal packing, is a ππ inter­action between arms 1 and 2, as seen in Fig. 5[link]b. These inter­actions are listed in Table 3[link].

[Figure 5]
Figure 5
ππ stacking between (a) arms 4 and 5 of adjacent mol­ecules and (b) arms 1 and 2 of the title compound.

Finally, a hydrogen-bonding network (Table 4[link]) is observed throughout the crystal, consisting of a C—H⋯O=C bonding pattern between the mol­ecules of the title compound, and a C—H⋯N≡C bonding pattern between the aceto­nitrile mol­ecules, as seen in Fig. 6[link].

Table 4
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯O11i 0.93 2.48 3.217 (2) 136
C19—H19⋯O9ii 0.93 2.58 3.277 (3) 132
C26—H26⋯O13 0.93 2.56 3.147 (3) 121
C39—H39B⋯O7iii 0.96 2.49 3.443 (3) 174
C44—H44⋯O2iii 0.93 2.59 3.446 (3) 153
C65—H65⋯O14iv 0.93 2.40 3.112 (3) 133
C80—H80⋯O5i 0.93 2.33 3.235 (2) 164
C82—H82⋯O3v 0.93 2.51 3.278 (3) 141
C83—H83⋯O4v 0.93 2.53 3.289 (2) 139
C88—H88⋯O7i 0.93 2.53 3.313 (3) 142
C89—H89⋯O3vi 0.93 2.44 3.323 (3) 159
C93—H93B⋯O5vii 0.96 2.57 3.341 (4) 137
C97—H97B⋯O10 0.96 2.31 3.072 (3) 1361
C51—H51⋯N3 0.98 2.55 3.000 (3) 108
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x, y+1, z; (v) -x+1, -y+2, -z+1; (vi) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (vii) -x, -y+1, -z+1.
[Figure 6]
Figure 6
Part of the C—H⋯O=C bonding pattern between mol­ecules of the title compound and also part of the C—H⋯N≡C bonding pattern between the aceto­nitrile mol­ecules.

4. Database survey

A search of the Cambridge Structural Database (CSD Version 5.39, update of August 2018; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) for the mol­ecular formula (C46H26N2O7) and for unit-cell dimensions yielded no results. Searching for the various arms yielded 72 hits for indanone and 38 hits for indandione. Similar structures that contain eight-membered rings and are the result of aldol condensation, namely 1-(1,3-dioxoindan-2-yl­idene)-2-[spiro-1,3-indandione-2,18′-(5′H,9b′H,12′H,16b′H-5′,12′-dioxo-9b′,16b′-methano-11′-methyl­tri­indeno­(1,2-b:1,2-d:1,2-f)oxocin-17-yl)]inden-3-yl acetate and spiro­(1,3-indandione-2,10′-5′H,9b′H,10′H,16′H-5′,16′-dioxobenzo[a]di­indeno[1,2-f:1,2-h]azulen-11′-yl acetate) have been published previously (refcodes MEKQIC, MEKQEY; Jacob et al., 2000[Jacob, K., Sigalov, M., Becker, J. Y., Ellern, A. & Khodorkovsky, V. (2000). Eur. J. Org. Chem. pp. 2047-2055.]).

5. Synthesis and crystallization

The synthetic procedure for the title compound will be published elsewhere. The title compound was crystallized in HPLC/gradient grade aceto­nitrile (99.9%) obtained from Sigma (CAS 75-05-8) by slow evaporation at a temperature of 277 K over the course of several weeks, resulting in yellow crystals.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5[link]. Hydrogen atoms were placed at calculated positions (C—H = 0.93–0.98 Å) and refined in riding mode, with Uiso(H) = 1.2Ueq(C) for CH and CH2 groups and 1.5Ueq(C) for CH3 groups.

Table 5
Experimental details

Crystal data
Chemical formula C46H26N2O7·1.5C2H3N
Mr 780.27
Crystal system, space group Monoclinic, P21/c
Temperature (K) 100
a, b, c (Å) 13.5195 (3), 13.0697 (3), 42.9248 (9)
β (°) 92.475 (2)
V3) 7577.6 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.09
Crystal size (mm) 0.32 × 0.31 × 0.29
 
Data collection
Diffractometer Rigaku Oxford Diffraction XtaLAB Synergy, Dualflex, HyPix
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2018[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.723, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 81627, 13290, 11196
Rint 0.050
(sin θ/λ)max−1) 0.594
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.122, 1.03
No. of reflections 13290
No. of parameters 1077
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.15, −0.43
Computer programs: CrysAlis PRO (Rigaku OD, 2018[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2018 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]) and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Supporting information


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

rac-11'-(1-Acetyl-1H-indazol-3-yl)-11',11a'-dihydro-10'H,17'H-spiro[indene-2,18'-[5a,16b]methanotriindeno[1,2-b:1',2'-d:2'',1''-g]oxocine]-1,3,10',12',17'(10a'H)-pentaone acetonitrile 1.5-solvate top
Crystal data top
C46H26N2O7·1.5C2H3NF(000) = 3240
Mr = 780.27Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.5195 (3) ÅCell parameters from 32475 reflections
b = 13.0697 (3) Åθ = 2.4–25.1°
c = 42.9248 (9) ŵ = 0.09 mm1
β = 92.475 (2)°T = 100 K
V = 7577.6 (3) Å3Cube, clear yellow
Z = 40.32 × 0.31 × 0.29 mm
Data collection top
Rigaku Oxford Diffraction XtaLAB Synergy, Dualflex, HyPix
diffractometer
11196 reflections with I > 2σ(I)
ω scansRint = 0.050
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2018)
θmax = 25.0°, θmin = 2.2°
Tmin = 0.723, Tmax = 1.000h = 1615
81627 measured reflectionsk = 1515
13290 independent reflectionsl = 5050
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.122 w = 1/[σ2(Fo2) + (0.0537P)2 + 7.2184P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
13290 reflectionsΔρmax = 1.15 e Å3
1077 parametersΔρmin = 0.43 e Å3
Special details top

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.

Refinement. 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C5(H5), C51(H51), C3(H3), C4(H4), C49(H49), C50(H50) 2.b Aromatic/amide H refined with riding coordinates: C21(H21), C11(H11), C87(H87), C14(H14), C18(H18), C59(H59), C56(H56), C25(H25), C90(H90), C63(H63), C71(H71), C83(H83), C88(H88), C74(H74), C28(H28), C19(H19), C20(H20), C13(H13), C89(H89), C72(H72), C12(H12), C66(H66), C64(H64), C33(H33), C27(H27), C58(H58), C73(H73), C80(H80), C57(H57), C26(H26), C82(H82), C65(H65), C81(H81), C36(H36), C45(H45), C34(H34), C35(H35), C44(H44), C42(H42), C43(H43) 2.c Idealised Me refined as rotating group: C77(H77A,H77B,H77C), C39(H39A,H39B,H39C), C95(H95A,H95B,H95C), C97(H97A,H97B, H97C), C93(H93A,H93B,H93C)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O40.28132 (9)0.90383 (11)0.35064 (3)0.0193 (3)
O50.06102 (10)0.85056 (11)0.35809 (3)0.0213 (3)
O20.31863 (10)1.12073 (11)0.31418 (3)0.0208 (3)
O80.26418 (10)0.69691 (11)0.60733 (3)0.0195 (3)
O110.20536 (10)0.91667 (11)0.60793 (3)0.0223 (3)
O120.55174 (10)0.86716 (11)0.62155 (3)0.0213 (3)
O30.36007 (10)0.75907 (11)0.29532 (3)0.0243 (3)
O140.41342 (11)0.33440 (11)0.50365 (3)0.0280 (3)
O130.27308 (11)0.83008 (11)0.50520 (3)0.0246 (3)
O10.01317 (10)0.79294 (11)0.29860 (3)0.0247 (3)
O100.64519 (10)0.84199 (12)0.55745 (3)0.0271 (3)
O90.59079 (11)0.62756 (12)0.64619 (3)0.0284 (3)
O60.11865 (13)0.96381 (14)0.15127 (3)0.0378 (4)
N40.45944 (12)0.46736 (13)0.53442 (4)0.0193 (4)
N30.43295 (12)0.55669 (13)0.54928 (4)0.0199 (4)
N10.15198 (12)0.92208 (13)0.23177 (4)0.0203 (4)
N20.17098 (13)0.95505 (14)0.20192 (4)0.0233 (4)
O70.07690 (12)1.13677 (12)0.28272 (4)0.0363 (4)
C310.22625 (14)0.95317 (15)0.24976 (4)0.0177 (4)
C840.43465 (14)0.97866 (15)0.64481 (4)0.0174 (4)
C90.23404 (14)1.09819 (15)0.31912 (4)0.0163 (4)
C850.46741 (14)0.89491 (15)0.62467 (4)0.0165 (4)
C860.35501 (14)0.73340 (15)0.65495 (4)0.0180 (4)
C10.10267 (13)0.89504 (15)0.33917 (4)0.0154 (4)
C50.17008 (13)1.02282 (15)0.29968 (4)0.0155 (4)
H50.1415401.0631530.2822690.019*
C300.02326 (14)0.87827 (15)0.36358 (4)0.0168 (4)
C60.08157 (13)0.99648 (15)0.32018 (4)0.0160 (4)
C510.47739 (14)0.77743 (15)0.56304 (4)0.0182 (4)
H510.4605850.7479220.5424970.022*
C780.29135 (14)0.92053 (15)0.61719 (4)0.0173 (4)
C30.19119 (14)0.82563 (15)0.29181 (4)0.0167 (4)
H30.1658090.7972370.2719030.020*
C790.33333 (14)0.99391 (15)0.64028 (5)0.0185 (4)
C240.16981 (14)0.91786 (15)0.39245 (4)0.0188 (4)
C160.27514 (14)0.75419 (15)0.30310 (4)0.0182 (4)
C150.07922 (14)1.08829 (15)0.34193 (4)0.0178 (4)
C220.13573 (14)0.70507 (15)0.32975 (4)0.0172 (4)
C100.16932 (14)1.14016 (15)0.34290 (4)0.0175 (4)
C170.23202 (14)0.67764 (15)0.32367 (4)0.0185 (4)
C40.22699 (14)0.93492 (15)0.28442 (4)0.0164 (4)
H40.2960520.9397790.2921980.020*
C290.06897 (14)0.90144 (15)0.39466 (5)0.0187 (4)
C530.29273 (14)0.78625 (15)0.55976 (4)0.0187 (4)
C690.51264 (14)0.58956 (15)0.56452 (4)0.0179 (4)
C470.37501 (13)0.84789 (15)0.60764 (4)0.0159 (4)
C520.38474 (14)0.84001 (15)0.57150 (4)0.0169 (4)
C490.44528 (14)0.66568 (15)0.61239 (4)0.0185 (4)
H490.4161500.5976430.6091600.022*
C750.55841 (14)0.44390 (15)0.54100 (4)0.0188 (4)
C500.50919 (14)0.68575 (15)0.58370 (4)0.0183 (4)
H500.5768620.6994020.5917270.022*
C680.55696 (14)0.85675 (16)0.55727 (4)0.0204 (4)
C20.10881 (13)0.80699 (15)0.31525 (4)0.0166 (4)
C620.40457 (15)0.94379 (16)0.55710 (4)0.0192 (4)
C910.44309 (14)0.69583 (16)0.66803 (5)0.0203 (4)
C210.07741 (15)0.64118 (16)0.34713 (5)0.0211 (4)
H210.0126790.6588790.3513010.025*
C70.00955 (14)0.97595 (17)0.30021 (5)0.0229 (5)
C700.59492 (14)0.52222 (15)0.56063 (4)0.0190 (4)
C320.29768 (15)1.00870 (16)0.23258 (5)0.0222 (4)
C110.18869 (15)1.21979 (16)0.36388 (5)0.0215 (4)
H110.2495311.2530920.3647300.026*
C540.24333 (14)0.72063 (15)0.57739 (4)0.0185 (4)
C920.50673 (15)0.65964 (16)0.64332 (5)0.0210 (4)
C870.28013 (15)0.76636 (15)0.67365 (5)0.0202 (4)
H870.2202490.7900790.6649410.024*
C230.19807 (14)0.90563 (14)0.35990 (4)0.0161 (4)
C480.35832 (14)0.73736 (15)0.61983 (4)0.0174 (4)
C670.50352 (15)0.95311 (16)0.54991 (4)0.0212 (4)
C610.24575 (14)0.78555 (15)0.52835 (5)0.0194 (4)
C550.15761 (14)0.67421 (15)0.55995 (5)0.0196 (4)
C140.00486 (15)1.11728 (16)0.36125 (5)0.0220 (4)
H140.0559271.0838490.3604670.026*
C600.15772 (14)0.71537 (15)0.52989 (5)0.0201 (4)
C180.27387 (15)0.58672 (16)0.33491 (5)0.0231 (4)
H180.3389000.5694400.3309970.028*
C760.38810 (15)0.40956 (16)0.51779 (5)0.0219 (4)
C590.08710 (15)0.68832 (17)0.50747 (5)0.0240 (4)
H590.0870210.7161880.4875380.029*
C560.08756 (15)0.60420 (16)0.56834 (5)0.0241 (4)
H560.0876540.5769290.5883540.029*
C250.22988 (15)0.94249 (17)0.41844 (5)0.0236 (4)
H250.2974330.9536700.4169280.028*
C900.46040 (16)0.69348 (18)0.70026 (5)0.0258 (5)
H900.5200660.6692180.7089690.031*
C460.12284 (15)0.87633 (18)0.26946 (5)0.0248 (5)
C630.33856 (16)1.02290 (16)0.55081 (5)0.0237 (4)
H630.2724391.0173280.5557080.028*
C710.69291 (15)0.52004 (17)0.57239 (5)0.0229 (4)
H710.7180130.5723240.5851220.027*
C830.49062 (15)1.03680 (16)0.66609 (5)0.0229 (4)
H830.5584761.0266780.6690280.027*
C370.26021 (16)1.00706 (16)0.20159 (5)0.0242 (4)
C880.29727 (15)0.76286 (16)0.70568 (5)0.0232 (4)
H880.2479300.7842310.7186520.028*
C80.03363 (14)0.87959 (17)0.29088 (5)0.0225 (4)
C740.61798 (15)0.36241 (16)0.53240 (5)0.0227 (4)
H740.5942160.3115550.5189000.027*
C280.02389 (16)0.90879 (17)0.42301 (5)0.0241 (4)
H280.0437550.8981210.4245040.029*
C190.21529 (16)0.52303 (16)0.35208 (5)0.0250 (5)
H190.2409400.4614340.3596730.030*
C200.11859 (16)0.55002 (16)0.35812 (5)0.0244 (5)
H200.0806120.5061100.3697590.029*
C130.02341 (16)1.19748 (16)0.38178 (5)0.0257 (5)
H130.0259611.2183670.3948070.031*
C890.38716 (16)0.72789 (17)0.71885 (5)0.0264 (5)
H890.3976040.7278700.7404120.032*
C720.75127 (15)0.43839 (18)0.56462 (5)0.0262 (5)
H720.8162710.4346460.5725540.031*
C120.11470 (16)1.24760 (17)0.38333 (5)0.0260 (5)
H120.1257231.3002750.3976250.031*
C660.53873 (16)1.04115 (17)0.53591 (5)0.0266 (5)
H660.6048501.0469990.5310390.032*
N50.41672 (18)0.3769 (2)0.60410 (6)0.0511 (6)
C640.37410 (17)1.11076 (17)0.53697 (5)0.0297 (5)
H640.3310321.1649010.5326360.036*
C330.38850 (16)1.05521 (17)0.24042 (5)0.0276 (5)
H330.4134751.0571920.2609430.033*
C270.08355 (17)0.93258 (18)0.44892 (5)0.0294 (5)
H270.0554860.9372920.4682670.035*
C580.01558 (15)0.61773 (17)0.51561 (5)0.0270 (5)
H580.0332940.5983390.5008760.032*
C380.10284 (17)0.93256 (17)0.17729 (5)0.0283 (5)
C730.71375 (16)0.36069 (17)0.54484 (5)0.0257 (5)
H730.7547600.3063790.5399720.031*
C800.28412 (15)1.06837 (17)0.65691 (5)0.0256 (5)
H800.2163361.0787430.6538580.031*
N60.00183 (19)0.34600 (18)0.57506 (6)0.0506 (6)
C570.01584 (16)0.57579 (17)0.54527 (5)0.0278 (5)
H570.0322560.5280310.5499830.033*
C260.18458 (17)0.94969 (19)0.44679 (5)0.0294 (5)
H260.2224910.9662410.4646750.035*
C410.15187 (17)0.97597 (17)0.26401 (5)0.0294 (5)
C820.44174 (16)1.11052 (18)0.68282 (5)0.0302 (5)
H820.4772721.1501580.6973990.036*
C650.47261 (17)1.11946 (18)0.52948 (5)0.0316 (5)
H650.4942931.1788820.5200020.038*
C810.33991 (16)1.12624 (18)0.67813 (6)0.0315 (5)
H810.3090561.1766710.6895130.038*
C360.31232 (18)1.05022 (18)0.17746 (5)0.0326 (5)
H360.2879061.0487660.1568700.039*
C450.17277 (18)0.79450 (18)0.25547 (6)0.0344 (5)
H450.1532280.7271080.2589810.041*
C340.43964 (19)1.09806 (19)0.21652 (6)0.0370 (6)
H340.5003301.1294710.2209800.044*
C770.28359 (16)0.44554 (18)0.51910 (5)0.0300 (5)
H77A0.2751150.5068150.5069410.045*
H77B0.2686800.4594490.5403450.045*
H77C0.2397410.3934840.5108400.045*
C400.07762 (16)1.04316 (17)0.28265 (5)0.0267 (5)
C960.48059 (19)0.3199 (2)0.60569 (5)0.0356 (6)
C390.01509 (18)0.87178 (19)0.18588 (5)0.0343 (5)
H39A0.0228880.9102660.2001980.051*
H39B0.0366830.8089060.1955330.051*
H39C0.0251490.8569330.1674630.051*
C350.4017 (2)1.0950 (2)0.18577 (6)0.0395 (6)
H350.4383681.1244420.1702630.047*
C440.25598 (18)0.8201 (2)0.23537 (6)0.0372 (6)
H440.2931320.7686060.2255200.045*
C420.22916 (18)0.9994 (2)0.24452 (6)0.0383 (6)
H420.2469051.0671160.2406080.046*
C940.0808 (2)0.3293 (2)0.58371 (6)0.0402 (6)
N70.87013 (18)0.8519 (3)0.47954 (6)0.0652 (8)
C430.28084 (18)0.9204 (2)0.23065 (6)0.0415 (6)
H430.3351920.9356020.2174470.050*
C980.86308 (18)0.8262 (2)0.50448 (6)0.0433 (7)
C950.5620 (2)0.2478 (3)0.60822 (7)0.0524 (7)
H95A0.5469010.1892240.5953870.079*
H95B0.5718430.2265140.6295390.079*
H95C0.6212130.2798700.6014260.079*
C970.8546 (2)0.7937 (3)0.53653 (7)0.0605 (9)
H97A0.8282970.7255430.5369230.091*
H97B0.8111320.8393390.5468940.091*
H97C0.9188070.7947900.5469940.091*
C930.1807 (2)0.3063 (3)0.59497 (9)0.0755 (12)
H93A0.2121210.2634140.5801640.113*
H93B0.1789310.2714790.6146230.113*
H93C0.2174470.3688230.5975840.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0145 (7)0.0234 (8)0.0200 (7)0.0007 (6)0.0003 (5)0.0000 (6)
O50.0159 (7)0.0222 (8)0.0259 (7)0.0003 (6)0.0011 (6)0.0011 (6)
O20.0164 (7)0.0216 (8)0.0244 (7)0.0026 (6)0.0000 (5)0.0014 (6)
O80.0182 (7)0.0195 (7)0.0204 (7)0.0034 (6)0.0032 (5)0.0014 (6)
O110.0154 (7)0.0240 (8)0.0272 (7)0.0012 (6)0.0030 (6)0.0009 (6)
O120.0155 (7)0.0257 (8)0.0226 (7)0.0026 (6)0.0011 (5)0.0041 (6)
O30.0206 (8)0.0258 (8)0.0269 (8)0.0052 (6)0.0054 (6)0.0013 (6)
O140.0386 (9)0.0179 (8)0.0270 (8)0.0003 (7)0.0052 (6)0.0035 (6)
O130.0300 (8)0.0243 (8)0.0193 (7)0.0023 (6)0.0008 (6)0.0021 (6)
O10.0197 (7)0.0272 (8)0.0266 (8)0.0002 (6)0.0044 (6)0.0044 (6)
O100.0193 (8)0.0292 (9)0.0331 (8)0.0027 (6)0.0037 (6)0.0001 (7)
O90.0249 (8)0.0348 (9)0.0255 (8)0.0121 (7)0.0005 (6)0.0029 (7)
O60.0477 (10)0.0469 (11)0.0183 (8)0.0123 (8)0.0033 (7)0.0020 (7)
N40.0215 (9)0.0171 (9)0.0193 (8)0.0000 (7)0.0002 (7)0.0032 (7)
N30.0213 (9)0.0177 (9)0.0207 (8)0.0009 (7)0.0005 (7)0.0021 (7)
N10.0255 (9)0.0206 (9)0.0146 (8)0.0023 (7)0.0004 (7)0.0008 (7)
N20.0305 (10)0.0240 (10)0.0152 (8)0.0032 (8)0.0005 (7)0.0020 (7)
O70.0377 (9)0.0243 (9)0.0457 (10)0.0009 (7)0.0114 (8)0.0001 (7)
C310.0205 (10)0.0151 (10)0.0176 (10)0.0028 (8)0.0019 (8)0.0014 (8)
C840.0156 (9)0.0172 (10)0.0195 (9)0.0002 (8)0.0012 (7)0.0010 (8)
C90.0186 (10)0.0146 (10)0.0154 (9)0.0012 (8)0.0016 (7)0.0032 (7)
C850.0169 (10)0.0169 (10)0.0156 (9)0.0000 (8)0.0006 (7)0.0027 (8)
C860.0204 (10)0.0141 (10)0.0194 (10)0.0019 (8)0.0002 (8)0.0015 (8)
C10.0133 (9)0.0151 (10)0.0177 (9)0.0012 (7)0.0012 (7)0.0012 (8)
C50.0163 (9)0.0154 (10)0.0146 (9)0.0002 (7)0.0008 (7)0.0017 (7)
C300.0166 (10)0.0119 (9)0.0219 (10)0.0020 (7)0.0016 (8)0.0012 (8)
C60.0149 (9)0.0152 (10)0.0179 (9)0.0012 (7)0.0010 (7)0.0004 (8)
C510.0203 (10)0.0182 (10)0.0159 (9)0.0012 (8)0.0003 (7)0.0009 (8)
C780.0170 (10)0.0170 (10)0.0180 (9)0.0013 (8)0.0010 (7)0.0051 (8)
C30.0184 (9)0.0167 (10)0.0147 (9)0.0011 (8)0.0010 (7)0.0009 (8)
C790.0174 (10)0.0162 (10)0.0219 (10)0.0005 (8)0.0001 (8)0.0019 (8)
C240.0200 (10)0.0163 (10)0.0201 (10)0.0024 (8)0.0000 (8)0.0044 (8)
C160.0190 (10)0.0198 (11)0.0157 (9)0.0034 (8)0.0002 (7)0.0035 (8)
C150.0212 (10)0.0145 (10)0.0175 (9)0.0021 (8)0.0016 (8)0.0029 (8)
C220.0204 (10)0.0155 (10)0.0155 (9)0.0011 (8)0.0028 (7)0.0015 (8)
C100.0199 (10)0.0163 (10)0.0161 (9)0.0030 (8)0.0019 (7)0.0029 (8)
C170.0212 (10)0.0177 (10)0.0163 (9)0.0016 (8)0.0014 (7)0.0013 (8)
C40.0152 (9)0.0175 (10)0.0165 (9)0.0008 (8)0.0007 (7)0.0010 (8)
C290.0205 (10)0.0156 (10)0.0201 (10)0.0009 (8)0.0006 (8)0.0021 (8)
C530.0165 (9)0.0189 (10)0.0202 (10)0.0017 (8)0.0024 (8)0.0033 (8)
C690.0189 (10)0.0178 (10)0.0171 (9)0.0008 (8)0.0011 (7)0.0014 (8)
C470.0145 (9)0.0156 (10)0.0174 (9)0.0009 (7)0.0021 (7)0.0000 (8)
C520.0170 (9)0.0168 (10)0.0167 (9)0.0010 (8)0.0017 (7)0.0004 (8)
C490.0207 (10)0.0165 (10)0.0182 (10)0.0019 (8)0.0002 (8)0.0010 (8)
C750.0220 (10)0.0188 (10)0.0159 (9)0.0001 (8)0.0024 (8)0.0017 (8)
C500.0173 (9)0.0191 (10)0.0185 (9)0.0002 (8)0.0000 (7)0.0014 (8)
C680.0200 (11)0.0245 (11)0.0166 (9)0.0033 (8)0.0011 (8)0.0023 (8)
C20.0129 (9)0.0180 (10)0.0187 (9)0.0006 (8)0.0026 (7)0.0012 (8)
C620.0232 (10)0.0195 (10)0.0146 (9)0.0043 (8)0.0036 (8)0.0004 (8)
C910.0195 (10)0.0193 (10)0.0221 (10)0.0012 (8)0.0004 (8)0.0020 (8)
C210.0225 (10)0.0175 (10)0.0236 (10)0.0009 (8)0.0027 (8)0.0016 (8)
C70.0112 (9)0.0323 (12)0.0249 (10)0.0010 (8)0.0018 (8)0.0147 (9)
C700.0212 (10)0.0192 (10)0.0169 (9)0.0003 (8)0.0031 (8)0.0014 (8)
C320.0289 (11)0.0164 (10)0.0219 (10)0.0005 (9)0.0071 (8)0.0008 (8)
C110.0251 (11)0.0182 (11)0.0210 (10)0.0020 (8)0.0025 (8)0.0002 (8)
C540.0180 (10)0.0173 (10)0.0201 (10)0.0011 (8)0.0009 (8)0.0025 (8)
C920.0216 (11)0.0195 (11)0.0217 (10)0.0038 (8)0.0001 (8)0.0031 (8)
C870.0197 (10)0.0170 (10)0.0239 (10)0.0005 (8)0.0015 (8)0.0033 (8)
C230.0172 (10)0.0118 (9)0.0190 (9)0.0009 (7)0.0012 (8)0.0020 (7)
C480.0156 (9)0.0159 (10)0.0207 (10)0.0014 (8)0.0009 (7)0.0001 (8)
C670.0231 (10)0.0218 (11)0.0182 (10)0.0048 (8)0.0039 (8)0.0011 (8)
C610.0199 (10)0.0175 (10)0.0206 (10)0.0026 (8)0.0012 (8)0.0015 (8)
C550.0159 (9)0.0177 (10)0.0249 (10)0.0024 (8)0.0018 (8)0.0053 (8)
C140.0211 (10)0.0180 (10)0.0273 (11)0.0021 (8)0.0047 (8)0.0022 (8)
C600.0198 (10)0.0168 (10)0.0238 (10)0.0025 (8)0.0019 (8)0.0034 (8)
C180.0244 (11)0.0212 (11)0.0233 (10)0.0066 (9)0.0013 (8)0.0006 (8)
C760.0292 (11)0.0173 (11)0.0188 (10)0.0038 (9)0.0035 (8)0.0039 (8)
C590.0251 (11)0.0239 (11)0.0227 (10)0.0044 (9)0.0020 (8)0.0028 (9)
C560.0263 (11)0.0191 (11)0.0269 (11)0.0003 (9)0.0008 (8)0.0007 (9)
C250.0213 (10)0.0285 (12)0.0206 (10)0.0011 (9)0.0027 (8)0.0031 (9)
C900.0245 (11)0.0319 (12)0.0206 (10)0.0042 (9)0.0019 (8)0.0029 (9)
C460.0162 (10)0.0376 (13)0.0203 (10)0.0016 (9)0.0031 (8)0.0033 (9)
C630.0239 (11)0.0221 (11)0.0246 (11)0.0008 (9)0.0045 (8)0.0022 (9)
C710.0229 (10)0.0259 (11)0.0198 (10)0.0002 (9)0.0004 (8)0.0035 (8)
C830.0173 (10)0.0253 (11)0.0259 (11)0.0006 (8)0.0001 (8)0.0043 (9)
C370.0318 (11)0.0201 (11)0.0208 (10)0.0038 (9)0.0036 (8)0.0004 (8)
C880.0270 (11)0.0205 (11)0.0228 (10)0.0001 (9)0.0075 (8)0.0010 (8)
C80.0169 (10)0.0317 (12)0.0189 (10)0.0004 (9)0.0001 (8)0.0042 (9)
C740.0284 (11)0.0190 (11)0.0211 (10)0.0002 (9)0.0048 (8)0.0008 (8)
C280.0231 (10)0.0276 (12)0.0221 (10)0.0020 (9)0.0051 (8)0.0028 (9)
C190.0334 (12)0.0182 (11)0.0231 (10)0.0069 (9)0.0028 (9)0.0030 (8)
C200.0322 (12)0.0185 (11)0.0226 (10)0.0020 (9)0.0015 (9)0.0016 (8)
C130.0338 (12)0.0207 (11)0.0232 (10)0.0038 (9)0.0085 (9)0.0017 (9)
C890.0321 (12)0.0295 (12)0.0175 (10)0.0007 (9)0.0003 (9)0.0019 (9)
C720.0202 (10)0.0319 (12)0.0265 (11)0.0050 (9)0.0004 (8)0.0003 (9)
C120.0381 (12)0.0200 (11)0.0198 (10)0.0010 (9)0.0007 (9)0.0050 (8)
C660.0259 (11)0.0273 (12)0.0260 (11)0.0102 (9)0.0052 (9)0.0046 (9)
N50.0479 (14)0.0571 (16)0.0494 (14)0.0082 (13)0.0142 (11)0.0171 (12)
C640.0328 (12)0.0214 (12)0.0342 (12)0.0021 (9)0.0079 (10)0.0056 (9)
C330.0304 (12)0.0240 (12)0.0286 (11)0.0059 (9)0.0053 (9)0.0018 (9)
C270.0337 (12)0.0372 (13)0.0178 (10)0.0011 (10)0.0058 (9)0.0034 (9)
C580.0232 (11)0.0250 (12)0.0321 (12)0.0005 (9)0.0080 (9)0.0082 (9)
C380.0377 (13)0.0269 (12)0.0196 (11)0.0108 (10)0.0058 (9)0.0020 (9)
C730.0254 (11)0.0247 (12)0.0277 (11)0.0064 (9)0.0078 (9)0.0006 (9)
C800.0186 (10)0.0230 (11)0.0353 (12)0.0034 (8)0.0009 (9)0.0038 (9)
N60.0529 (15)0.0372 (13)0.0619 (15)0.0033 (11)0.0037 (12)0.0124 (12)
C570.0229 (11)0.0203 (11)0.0402 (13)0.0062 (9)0.0006 (9)0.0022 (10)
C260.0328 (12)0.0389 (14)0.0159 (10)0.0006 (10)0.0042 (9)0.0018 (9)
C410.0399 (13)0.0242 (12)0.0242 (11)0.0034 (10)0.0013 (9)0.0009 (9)
C820.0243 (11)0.0296 (13)0.0365 (12)0.0023 (9)0.0003 (9)0.0141 (10)
C650.0368 (13)0.0233 (12)0.0337 (12)0.0101 (10)0.0083 (10)0.0096 (10)
C810.0245 (11)0.0271 (12)0.0431 (13)0.0023 (9)0.0044 (10)0.0150 (10)
C360.0471 (14)0.0279 (13)0.0234 (11)0.0031 (11)0.0089 (10)0.0053 (9)
C450.0446 (14)0.0209 (12)0.0385 (13)0.0081 (10)0.0106 (11)0.0030 (10)
C340.0397 (14)0.0330 (14)0.0391 (14)0.0122 (11)0.0130 (11)0.0002 (11)
C770.0263 (11)0.0269 (12)0.0363 (12)0.0042 (9)0.0056 (9)0.0015 (10)
C400.0280 (11)0.0235 (12)0.0284 (11)0.0001 (9)0.0022 (9)0.0012 (9)
C960.0395 (14)0.0432 (15)0.0245 (12)0.0004 (12)0.0052 (10)0.0067 (11)
C390.0418 (14)0.0322 (13)0.0277 (12)0.0003 (11)0.0141 (10)0.0011 (10)
C350.0517 (16)0.0329 (14)0.0355 (13)0.0064 (12)0.0202 (12)0.0068 (11)
C440.0401 (14)0.0368 (14)0.0341 (13)0.0156 (11)0.0074 (10)0.0116 (11)
C420.0382 (14)0.0324 (14)0.0436 (14)0.0042 (11)0.0068 (11)0.0035 (11)
C940.0470 (16)0.0321 (14)0.0419 (14)0.0078 (12)0.0058 (12)0.0084 (11)
N70.0392 (13)0.109 (2)0.0481 (15)0.0146 (14)0.0087 (11)0.0306 (16)
C430.0297 (13)0.0428 (16)0.0504 (15)0.0011 (11)0.0152 (11)0.0120 (12)
C980.0276 (13)0.0573 (18)0.0454 (16)0.0122 (12)0.0071 (11)0.0108 (13)
C950.0523 (17)0.062 (2)0.0424 (15)0.0185 (15)0.0022 (13)0.0110 (14)
C970.071 (2)0.063 (2)0.0493 (17)0.0325 (17)0.0279 (15)0.0133 (15)
C930.0429 (17)0.099 (3)0.084 (2)0.0192 (18)0.0034 (16)0.043 (2)
Geometric parameters (Å, º) top
O4—C231.210 (2)C87—C881.385 (3)
O5—C301.209 (2)C67—C661.391 (3)
O2—C91.209 (2)C61—C601.506 (3)
O8—C541.340 (2)C55—C601.398 (3)
O8—C481.459 (2)C55—C561.376 (3)
O11—C781.213 (2)C14—H140.9300
O12—C851.209 (2)C14—C131.386 (3)
O3—C161.211 (2)C60—C591.372 (3)
O14—C761.212 (3)C18—H180.9300
O13—C611.222 (2)C18—C191.383 (3)
O1—C21.462 (2)C76—C771.492 (3)
O1—C81.332 (3)C59—H590.9300
O10—C681.208 (2)C59—C581.392 (3)
O9—C921.213 (2)C56—H560.9300
O6—C381.217 (3)C56—C571.406 (3)
N4—N31.385 (2)C25—H250.9300
N4—C751.390 (3)C25—C261.389 (3)
N4—C761.397 (3)C90—H900.9300
N3—C691.309 (3)C90—C891.374 (3)
N1—N21.386 (2)C46—C81.485 (3)
N1—C311.305 (3)C46—C411.377 (3)
N2—C371.385 (3)C46—C451.387 (3)
N2—C381.403 (3)C63—H630.9300
O7—C401.223 (3)C63—C641.388 (3)
C31—C41.506 (3)C71—H710.9300
C31—C321.437 (3)C71—C721.377 (3)
C84—C851.475 (3)C83—H830.9300
C84—C791.389 (3)C83—C821.386 (3)
C84—C831.387 (3)C37—C361.397 (3)
C9—C51.534 (3)C88—H880.9300
C9—C101.478 (3)C88—C891.395 (3)
C85—C471.547 (3)C74—H740.9300
C86—C911.384 (3)C74—C731.379 (3)
C86—C871.387 (3)C28—H280.9300
C86—C481.511 (3)C28—C271.381 (3)
C1—C301.548 (3)C19—H190.9300
C1—C61.576 (3)C19—C201.389 (3)
C1—C21.547 (3)C20—H200.9300
C1—C231.541 (2)C13—H130.9300
C5—H50.9800C13—C121.396 (3)
C5—C61.554 (3)C89—H890.9300
C5—C41.544 (3)C72—H720.9300
C30—C291.478 (3)C72—C731.404 (3)
C6—C151.522 (3)C12—H120.9300
C6—C71.494 (3)C66—H660.9300
C51—H510.9800C66—C651.379 (3)
C51—C521.552 (3)N5—C961.140 (3)
C51—C501.541 (3)C64—H640.9300
C51—C681.522 (3)C64—C651.388 (3)
C78—C791.475 (3)C33—H330.9300
C78—C471.546 (3)C33—C341.380 (3)
C3—H30.9800C27—H270.9300
C3—C161.532 (3)C27—C261.391 (3)
C3—C41.546 (3)C58—H580.9300
C3—C21.552 (3)C58—C571.386 (3)
C79—C801.393 (3)C38—C391.487 (3)
C24—C291.387 (3)C73—H730.9300
C24—C231.473 (3)C80—H800.9300
C24—C251.389 (3)C80—C811.382 (3)
C16—C171.471 (3)N6—C941.137 (3)
C15—C101.393 (3)C57—H570.9300
C15—C141.383 (3)C26—H260.9300
C22—C171.386 (3)C41—C401.533 (3)
C22—C21.508 (3)C41—C421.345 (3)
C22—C211.388 (3)C82—H820.9300
C10—C111.394 (3)C82—C811.398 (3)
C17—C181.393 (3)C65—H650.9300
C4—H40.9800C81—H810.9300
C29—C281.388 (3)C36—H360.9300
C53—C521.497 (3)C36—C351.376 (4)
C53—C541.341 (3)C45—H450.9300
C53—C611.465 (3)C45—C441.427 (3)
C69—C501.504 (3)C34—H340.9300
C69—C701.434 (3)C34—C351.396 (4)
C47—C521.566 (3)C77—H77A0.9600
C47—C481.556 (3)C77—H77B0.9600
C52—C621.519 (3)C77—H77C0.9600
C49—H490.9800C96—C951.450 (4)
C49—C501.557 (3)C39—H39A0.9600
C49—C921.537 (3)C39—H39B0.9600
C49—C481.547 (3)C39—H39C0.9600
C75—C701.402 (3)C35—H350.9300
C75—C741.395 (3)C44—H440.9300
C50—H500.9800C44—C431.367 (4)
C68—C671.479 (3)C42—H420.9300
C62—C671.391 (3)C42—C431.369 (4)
C62—C631.385 (3)C94—C931.446 (4)
C91—C921.472 (3)N7—C981.130 (3)
C91—C901.393 (3)C43—H430.9300
C21—H210.9300C98—C971.449 (4)
C21—C201.389 (3)C95—H95A0.9600
C7—C81.357 (3)C95—H95B0.9600
C7—C401.458 (3)C95—H95C0.9600
C70—C711.397 (3)C97—H97A0.9600
C32—C371.403 (3)C97—H97B0.9600
C32—C331.398 (3)C97—H97C0.9600
C11—H110.9300C93—H93A0.9600
C11—C121.379 (3)C93—H93B0.9600
C54—C551.482 (3)C93—H93C0.9600
C87—H870.9300
C56···C973.381
C54—O8—C48114.40 (15)O13—C61—C53127.64 (19)
C8—O1—C2114.55 (16)O13—C61—C60126.34 (18)
N3—N4—C75110.99 (15)C53—C61—C60105.99 (17)
N3—N4—C76120.31 (16)C60—C55—C54106.07 (17)
C75—N4—C76128.46 (17)C56—C55—C54132.23 (19)
C69—N3—N4106.46 (16)C56—C55—C60121.70 (18)
C31—N1—N2106.35 (16)C15—C14—H14120.9
N1—N2—C38119.31 (17)C15—C14—C13118.17 (19)
C37—N2—N1111.01 (16)C13—C14—H14120.9
C37—N2—C38129.68 (18)C55—C60—C61107.87 (17)
N1—C31—C4120.49 (17)C59—C60—C61130.80 (19)
N1—C31—C32111.75 (17)C59—C60—C55121.31 (19)
C32—C31—C4127.65 (18)C17—C18—H18121.2
C79—C84—C85110.10 (17)C19—C18—C17117.67 (19)
C83—C84—C85128.56 (18)C19—C18—H18121.2
C83—C84—C79121.33 (18)O14—C76—N4119.38 (19)
O2—C9—C5125.23 (17)O14—C76—C77124.24 (19)
O2—C9—C10128.56 (18)N4—C76—C77116.38 (18)
C10—C9—C5106.10 (15)C60—C59—H59121.2
O12—C85—C84126.58 (18)C60—C59—C58117.7 (2)
O12—C85—C47125.06 (17)C58—C59—H59121.2
C84—C85—C47108.36 (15)C55—C56—H56121.5
C91—C86—C87120.80 (18)C55—C56—C57116.9 (2)
C91—C86—C48110.78 (17)C57—C56—H56121.5
C87—C86—C48128.33 (18)C24—C25—H25121.5
C30—C1—C6110.73 (15)C26—C25—C24117.05 (19)
C2—C1—C30113.74 (15)C26—C25—H25121.5
C2—C1—C6107.22 (15)C91—C90—H90120.8
C23—C1—C30102.10 (15)C89—C90—C91118.37 (19)
C23—C1—C6110.57 (15)C89—C90—H90120.8
C23—C1—C2112.49 (15)C41—C46—C8107.21 (19)
C9—C5—H5105.3C41—C46—C45121.7 (2)
C9—C5—C6105.32 (15)C45—C46—C8131.1 (2)
C9—C5—C4115.41 (15)C62—C63—H63121.0
C6—C5—H5105.3C62—C63—C64118.0 (2)
C4—C5—H5105.3C64—C63—H63121.0
C4—C5—C6119.03 (16)C70—C71—H71120.9
O5—C30—C1125.87 (17)C72—C71—C70118.2 (2)
O5—C30—C29126.24 (18)C72—C71—H71120.9
C29—C30—C1107.88 (15)C84—C83—H83121.2
C5—C6—C1110.65 (15)C82—C83—C84117.58 (19)
C15—C6—C1110.73 (15)C82—C83—H83121.2
C15—C6—C5102.11 (15)N2—C37—C32106.05 (17)
C7—C6—C1105.78 (15)N2—C37—C36132.3 (2)
C7—C6—C5110.55 (15)C36—C37—C32121.6 (2)
C7—C6—C15117.06 (16)C87—C88—H88119.4
C52—C51—H51105.1C87—C88—C89121.24 (19)
C50—C51—H51105.1C89—C88—H88119.4
C50—C51—C52118.88 (16)O1—C8—C7127.61 (18)
C68—C51—H51105.1O1—C8—C46119.59 (19)
C68—C51—C52105.21 (16)C7—C8—C46112.79 (19)
C68—C51—C50116.21 (16)C75—C74—H74121.5
O11—C78—C79125.63 (18)C73—C74—C75117.0 (2)
O11—C78—C47126.11 (18)C73—C74—H74121.5
C79—C78—C47108.23 (15)C29—C28—H28121.4
C16—C3—H3105.8C27—C28—C29117.29 (19)
C16—C3—C4113.20 (15)C27—C28—H28121.4
C16—C3—C2103.99 (15)C18—C19—H19119.6
C4—C3—H3105.8C18—C19—C20120.77 (19)
C4—C3—C2121.20 (16)C20—C19—H19119.6
C2—C3—H3105.8C21—C20—C19121.4 (2)
C84—C79—C78110.44 (17)C21—C20—H20119.3
C84—C79—C80121.22 (19)C19—C20—H20119.3
C80—C79—C78128.32 (18)C14—C13—H13119.3
C29—C24—C23110.13 (17)C14—C13—C12121.37 (19)
C29—C24—C25121.53 (18)C12—C13—H13119.3
C25—C24—C23128.34 (18)C90—C89—C88120.58 (19)
O3—C16—C3125.36 (18)C90—C89—H89119.7
O3—C16—C17127.32 (18)C88—C89—H89119.7
C17—C16—C3107.28 (16)C71—C72—H72119.6
C10—C15—C6111.13 (16)C71—C72—C73120.74 (19)
C14—C15—C6128.23 (18)C73—C72—H72119.6
C14—C15—C10120.41 (18)C11—C12—C13120.68 (19)
C17—C22—C2111.26 (17)C11—C12—H12119.7
C17—C22—C21120.37 (18)C13—C12—H12119.7
C21—C22—C2128.36 (18)C67—C66—H66121.0
C15—C10—C9109.98 (17)C65—C66—C67118.0 (2)
C15—C10—C11121.48 (18)C65—C66—H66121.0
C11—C10—C9128.53 (18)C63—C64—H64119.3
C22—C17—C16109.69 (17)C65—C64—C63121.3 (2)
C22—C17—C18121.74 (19)C65—C64—H64119.3
C18—C17—C16128.48 (18)C32—C33—H33121.3
C31—C4—C5108.61 (15)C34—C33—C32117.4 (2)
C31—C4—C3111.12 (16)C34—C33—H33121.3
C31—C4—H4107.0C28—C27—H27119.2
C5—C4—C3115.73 (15)C28—C27—C26121.64 (19)
C5—C4—H4107.0C26—C27—H27119.2
C3—C4—H4107.0C59—C58—H58119.4
C24—C29—C30110.10 (17)C57—C58—C59121.23 (19)
C24—C29—C28121.29 (19)C57—C58—H58119.4
C28—C29—C30128.60 (18)O6—C38—N2119.1 (2)
C54—C53—C52122.47 (17)O6—C38—C39125.5 (2)
C54—C53—C61107.98 (17)N2—C38—C39115.44 (18)
C61—C53—C52129.32 (18)C74—C73—C72122.1 (2)
N3—C69—C50120.24 (17)C74—C73—H73119.0
N3—C69—C70111.48 (17)C72—C73—H73119.0
C70—C69—C50128.27 (17)C79—C80—H80121.3
C85—C47—C52113.18 (15)C81—C80—C79117.44 (19)
C85—C47—C48109.61 (15)C81—C80—H80121.3
C78—C47—C85102.46 (15)C56—C57—H57119.4
C78—C47—C52113.40 (15)C58—C57—C56121.1 (2)
C78—C47—C48111.25 (15)C58—C57—H57119.4
C48—C47—C52106.96 (15)C25—C26—C27121.2 (2)
C51—C52—C47111.70 (15)C25—C26—H26119.4
C53—C52—C51109.94 (16)C27—C26—H26119.4
C53—C52—C47105.09 (15)C46—C41—C40106.12 (19)
C53—C52—C62116.14 (16)C42—C41—C46121.9 (2)
C62—C52—C51102.52 (15)C42—C41—C40131.9 (2)
C62—C52—C47111.61 (16)C83—C82—H82119.5
C50—C49—H49105.9C83—C82—C81121.1 (2)
C92—C49—H49105.9C81—C82—H82119.5
C92—C49—C50113.21 (16)C66—C65—C64120.9 (2)
C92—C49—C48103.88 (15)C66—C65—H65119.6
C48—C49—H49105.9C64—C65—H65119.6
C48—C49—C50120.92 (16)C80—C81—C82121.4 (2)
N4—C75—C70105.78 (17)C80—C81—H81119.3
N4—C75—C74132.58 (19)C82—C81—H81119.3
C74—C75—C70121.62 (19)C37—C36—H36121.8
C51—C50—C49115.83 (16)C35—C36—C37116.4 (2)
C51—C50—H50107.1C35—C36—H36121.8
C69—C50—C51110.46 (15)C46—C45—H45122.0
C69—C50—C49108.86 (16)C46—C45—C44115.9 (2)
C69—C50—H50107.1C44—C45—H45122.0
C49—C50—H50107.1C33—C34—H34119.5
O10—C68—C51126.50 (19)C33—C34—C35121.1 (2)
O10—C68—C67127.61 (19)C35—C34—H34119.5
C67—C68—C51105.82 (16)C76—C77—H77A109.5
O1—C2—C1110.26 (15)C76—C77—H77B109.5
O1—C2—C3110.31 (15)C76—C77—H77C109.5
O1—C2—C22106.47 (15)H77A—C77—H77B109.5
C1—C2—C3111.97 (15)H77A—C77—H77C109.5
C22—C2—C1113.71 (15)H77B—C77—H77C109.5
C22—C2—C3103.82 (15)O7—C40—C7126.6 (2)
C67—C62—C52110.90 (17)O7—C40—C41125.4 (2)
C63—C62—C52128.49 (18)C7—C40—C41108.01 (19)
C63—C62—C67120.61 (19)N5—C96—C95179.1 (3)
C86—C91—C92109.94 (17)C38—C39—H39A109.5
C86—C91—C90121.00 (19)C38—C39—H39B109.5
C90—C91—C92129.03 (18)C38—C39—H39C109.5
C22—C21—H21121.0H39A—C39—H39B109.5
C22—C21—C20118.03 (19)H39A—C39—H39C109.5
C20—C21—H21121.0H39B—C39—H39C109.5
C8—C7—C6121.15 (18)C36—C35—C34122.7 (2)
C8—C7—C40105.57 (18)C36—C35—H35118.7
C40—C7—C6132.4 (2)C34—C35—H35118.7
C75—C70—C69105.28 (17)C45—C44—H44120.1
C71—C70—C69134.30 (19)C43—C44—C45119.8 (2)
C71—C70—C75120.39 (19)C43—C44—H44120.1
C37—C32—C31104.82 (18)C41—C42—H42121.1
C33—C32—C31134.31 (19)C41—C42—C43117.8 (2)
C33—C32—C37120.83 (19)C43—C42—H42121.1
C10—C11—H11121.1N6—C94—C93179.0 (3)
C12—C11—C10117.85 (19)C44—C43—C42122.8 (2)
C12—C11—H11121.1C44—C43—H43118.6
O8—C54—C53126.87 (18)C42—C43—H43118.6
O8—C54—C55121.15 (17)N7—C98—C97179.6 (4)
C53—C54—C55111.98 (17)C96—C95—H95A109.5
O9—C92—C49125.08 (18)C96—C95—H95B109.5
O9—C92—C91127.74 (18)C96—C95—H95C109.5
C91—C92—C49107.14 (16)H95A—C95—H95B109.5
C86—C87—H87121.0H95A—C95—H95C109.5
C88—C87—C86117.96 (18)H95B—C95—H95C109.5
C88—C87—H87121.0C98—C97—H97A109.5
O4—C23—C1125.15 (17)C98—C97—H97B109.5
O4—C23—C24126.65 (17)C98—C97—H97C109.5
C24—C23—C1108.20 (15)H97A—C97—H97B109.5
O8—C48—C86106.96 (15)H97A—C97—H97C109.5
O8—C48—C47110.46 (15)H97B—C97—H97C109.5
O8—C48—C49111.29 (15)C94—C93—H93A109.5
C86—C48—C47112.23 (16)C94—C93—H93B109.5
C86—C48—C49103.93 (15)C94—C93—H93C109.5
C49—C48—C47111.72 (15)H93A—C93—H93B109.5
C62—C67—C68110.09 (18)H93A—C93—H93C109.5
C62—C67—C66121.2 (2)H93B—C93—H93C109.5
C66—C67—C68128.56 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O11i0.932.483.217 (2)136
C19—H19···O9ii0.932.583.277 (3)132
C26—H26···O130.932.563.147 (3)121
C39—H39B···O7iii0.962.493.443 (3)174
C44—H44···O2iii0.932.593.446 (3)153
C65—H65···O14iv0.932.403.112 (3)133
C80—H80···O5i0.932.333.235 (2)164
C82—H82···O3v0.932.513.278 (3)141
C83—H83···O4v0.932.533.289 (2)139
C88—H88···O7i0.932.533.313 (3)142
C89—H89···O3vi0.932.443.323 (3)159
C93—H93B···O5vii0.962.573.341 (4)137
C97—H97B···O100.962.313.072 (3)1361
C51—H51···N30.982.553.000 (3)108
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y+1, z+1; (iii) x, y1/2, z+1/2; (iv) x, y+1, z; (v) x+1, y+2, z+1; (vi) x, y+3/2, z+1/2; (vii) x, y+1, z+1.
Bond lengths (Å) in the central eight-membered ring of the molecule top
Atom pairBond lengthAtom pairBond length
C1—C21.547 (3)C5—C61.554 (3)
C1—C61.576 (3)C6—C71.494 (3)
C2—C31.552 (3)C7C81.357 (3)
C3—C41.546 (3)O1—C81.332 (3)
C4—C51.544 (3)O1—C21.462 (2)
The various arms extending from the central ring top
Arm designationCarbon atoms shared with central ringIUPAC name
1 (Fig. 3b)C5, C61-indanone
2 (Fig. 3c)C2, C31-indanone
3 (Fig. 3d)C11,3-indandione
4 (Fig. 3e)C41-(1H-indazol-1-yl)ethanone
5 (Fig. 3f)C7, C81-H-inden-1-one
Packing interactions found inside the crystal lattice (Å) top
Shortest bond distances that were found are shown for the various interactions.
InteractionC···C
C12 (Arm 1)···C97i (Acetonitrile)3.489 (3)
C26 (Arm 3)···C97i (Acetonitrile)3.475 (3)
C58 (Arm 2')···C97ii (Acetonitrile)3.317 (3)
C66 (Arm 1)···C66i (Arm 1')3.388 (2)
C32 (Arm 4)···C89iv (Arm 2')3.381 (3)
Symmetry codes: (i) 1 - x, 2 - y, 1 - z; (ii) x - 1, y, z; (iii) x, 3/2 - y, -1/2 + z.
 

Acknowledgements

We would like to warmly thank Professor Ira Weinstock for invaluable monetary and moral support.

Funding information

Funding for this research was provided by: Ben-Gurion University of the Negev.

References

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