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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1837–o1838.
Published online 2010 June 26. doi:  10.1107/S1600536810024499
PMCID: PMC3007086

(E)-7-(Pyren-1-yl)hept-6-enoic acid

Abstract

The title compound, C23H20O2, is a precursor of a pyrene-based supra­molecular element for non-covalent attachment to a carbon nanotube. The asymmetric unit contains three independent mol­ecules. The carb­oxy­lic acid group in each of these mol­ecules serves as an inter­molecular hydrogen-bond donor and acceptor, generating the commonly observed double O—H(...)O hydrogen-bond motif in an eight-membered ring. Weaker C—H(...)O, π–π [centroid–centroid distance = 3.968 (4) Å] and C—H(...)π inter­actions are also found in the crystal structure.

Related literature

Pyrene functionalized with an aliphatic spacer can be used to functionalize mol­ecular skeletons and the resulting mono- or multipyrene derivative bound non-covalently to a π-surface, see: Kavakka et al. (2007 [triangle]); Tomonari et al. (2006 [triangle]). For related structures, see: Bariamis et al. (2009 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). The title compound was synthesized by a Wittig reaction, see: Wittig & Haag (1955 [triangle]); Wittig & Schöllkopf (1954 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1837-scheme1.jpg

Experimental

Crystal data

  • C23H20O2
  • M r = 328.39
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1837-efi1.jpg
  • a = 10.7785 (3) Å
  • b = 13.3315 (4) Å
  • c = 18.9574 (6) Å
  • α = 103.287 (2)°
  • β = 103.064 (2)°
  • γ = 98.391 (2)°
  • V = 2525.64 (13) Å3
  • Z = 6
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 123 K
  • 0.32 × 0.14 × 0.06 mm

Data collection

  • Bruker–Nonius Kappa CCD diffractometer with an APEXII detector
  • 15113 measured reflections
  • 8885 independent reflections
  • 5729 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.164
  • S = 1.06
  • 8885 reflections
  • 685 parameters
  • 9 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.32 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: COLLECT (Bruker, 2008 [triangle]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and Mercury (Macrae et al., 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024499/fj2323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024499/fj2323Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the Academy of Finland (KR, project Nos. 212588 and 218325).

supplementary crystallographic information

Comment

Pyrene functionalized with an aliphatic spacer can be used to functionalize molecular skeletons and the resulting mono- or multipyrene derivative bound non-covalently to a pi-surface. Such a non-covalent functionalization has recently been reported by Kavakka et al. (Kavakka, et al., 2007) and Tomonari et al. (Tomonari, et al., 2006).

The title compound is synthesized by a Wittig reaction (Wittig & Schöllkopf, 1954; Wittig & Haag, 1955). In the molecule (Fig. 1) the planar pyrene ring is bonded to olefinic end carbon of hepten-6-oic acid chain and the pyrene is not coplanar with the conjugated double bond. In three independent molecules in asymmetric unit (labelled A, B and C) the hepten-6-oic acid side chains are almost straight and the dihedral angles between the pyrene rings and the double bonds are 34.8 (3), 14.5 (5) and 33.7 (2) °, respectively. Similar phenomenon was observed with (2E,4E,6E)-3-Methyl-7-(pyren-1-yl)octa-2,4,6-trienoic acid (Bariamis, et al., 2009), the trienoic acid derivative with two additional methyl groups in the positions of 3 and 7 in the side chain. Similar to that trienoic acid (Bariamis, et al., 2009) the carboxyl groups of three molecules of the title compound are connected to carboxyl group of another molecule with double hydrogen bonding interactions (Table 1), generating the R22(8) graph-set motif (Bernstein et al., 1995). With this motif one centrosymmetric BB pair and two non-centrosymmetric AC pairs were formed (Fig. 2). Mercury -program (Macrae et al., 2008) also finds some short intermolecular C—H···O, π–π [centroid-centroid distance 3.968 (4) Å] and weak C—H···π contacts (Table 1), which connect these pairs to each other and define the overall structure in the crystal.

Experimental

Bis(trimethylsilyl)amine (HMDS) (526 mg, 3.28 mmol) was dissolved in dry THF under inert atmosphere. 1.6-M n-BuLi (6.15 ml) was added at -10 °C temperature and the resulting solution was placed into dropping funnel and kept under inert atmosphere. (5-Carboxypentyl)triphenylphosphonium bromide (1.5 g, 3.28 mmol) was dissolved in dry THF under inert atmosphere. The solution was cooled to -10 °C and LiHMDS was added dropwise to the reaction flask. After addition the reaction mixture was stirred at room temperature for 20 minutes. Then the reaction mixture was cooled again (ice salt bath) and 1-pyrene carboxaldehyde (755 mg, 3.28 mmol), dissolved in dry THF, was added dropwise into reaction mixture under inert atmosphere. After addition the reaction mixture was stirred at room temperature for 1 h. The reaction was quenched with aq. 5% citric acid, extracted with DCM and obtained extract was evaporated to yield brown oil. Brown plates were crystallized out from this oil within two weeks. These plates were directly used in single-crystal analysis.

Refinement

All H atoms were visible in electron density maps, but those bonded to C were calculated at their idealized positions and allowed to ride on their parent atoms at C—H distances of 0.95 Å (aromatic, olefinic) and 0.99 Å (methylene), with Uiso(H) of 1.2 times Ueq(C). The O—H protons were found in the electron density map and were fixed in place by DFIX restraint (s = 0.02) at distances of 0.91 Å from N atoms, and Uiso(H) values of 1.5 times Ueq(O) were used.

Figures

Fig. 1.
View of the molecule A of title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
Fig. 2.
Packing diagram of the title compound showing the AC and BB pairs formed by O—H···O interactions between carboxyl groups.

Crystal data

C23H20O2Z = 6
Mr = 328.39F(000) = 1044
Triclinic, P1Dx = 1.295 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.7785 (3) ÅCell parameters from 10136 reflections
b = 13.3315 (4) Åθ = 0.4–28.3°
c = 18.9574 (6) ŵ = 0.08 mm1
α = 103.287 (2)°T = 123 K
β = 103.064 (2)°Plate, brown
γ = 98.391 (2)°0.32 × 0.14 × 0.06 mm
V = 2525.64 (13) Å3

Data collection

Bruker–Nonius Kappa CCD diffractometer with an APEXII detector5729 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 25.0°, θmin = 2.0°
Detector resolution: 9 pixels mm-1h = −12→12
[var phi] and ω scansk = −15→14
15113 measured reflectionsl = −22→22
8885 independent reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.051P)2 + 2.3851P] where P = (Fo2 + 2Fc2)/3
8885 reflections(Δ/σ)max < 0.001
685 parametersΔρmax = 0.32 e Å3
9 restraintsΔρmin = −0.39 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1A0.7011 (2)1.28351 (14)0.93924 (11)0.0334 (5)
O2A0.7089 (2)1.14559 (15)0.98730 (11)0.0325 (5)
H2O0.700 (3)1.190 (2)1.0269 (14)0.049*
C1A0.6787 (3)0.9784 (2)0.45311 (15)0.0231 (6)
C2A0.6764 (3)0.8741 (2)0.45537 (15)0.0270 (6)
H2A0.68680.85840.50250.032*
C3A0.6597 (3)0.7931 (2)0.39162 (15)0.0273 (6)
H3A0.65690.72310.39560.033*
C4A0.6467 (2)0.8129 (2)0.32122 (15)0.0217 (6)
C5A0.6330 (3)0.7317 (2)0.25410 (15)0.0262 (6)
H5A0.62930.66100.25670.031*
C6A0.6252 (3)0.7529 (2)0.18704 (16)0.0285 (6)
H6A0.61740.69730.14370.034*
C7A0.6286 (2)0.8582 (2)0.18038 (15)0.0227 (6)
C8A0.6204 (3)0.8833 (2)0.11204 (16)0.0307 (7)
H8A0.61400.82920.06810.037*
C9A0.6215 (3)0.9859 (2)0.10714 (16)0.0327 (7)
H9A0.61781.00140.06030.039*
C10A0.6281 (3)1.0657 (2)0.17000 (16)0.0290 (7)
H10A0.62621.13520.16580.035*
C11A0.6375 (2)1.0444 (2)0.23970 (15)0.0228 (6)
C12A0.6431 (3)1.1248 (2)0.30620 (15)0.0259 (6)
H12A0.63781.19400.30250.031*
C13A0.6556 (3)1.1044 (2)0.37389 (15)0.0235 (6)
H13A0.65981.15980.41660.028*
C14A0.6628 (2)1.0011 (2)0.38260 (14)0.0199 (6)
C15A0.6496 (2)0.91896 (19)0.31704 (14)0.0190 (6)
C16A0.6386 (2)0.9403 (2)0.24570 (14)0.0203 (6)
C17A0.6997 (3)1.0615 (2)0.52346 (16)0.0299 (7)
H17A0.74881.12860.52720.036*
C18A0.6569 (3)1.0513 (2)0.58107 (15)0.0292 (7)
H18A0.60670.98410.57620.035*
C19A0.6775 (3)1.1329 (2)0.65390 (15)0.0256 (6)
H19A0.60151.16700.65120.031*
H19B0.75531.18780.66130.031*
C20A0.6958 (3)1.08693 (19)0.72159 (14)0.0214 (6)
H20A0.62261.02680.71170.026*
H20B0.77721.05970.72760.026*
C21A0.7024 (3)1.1674 (2)0.79478 (14)0.0219 (6)
H21A0.62361.19800.78800.026*
H21B0.77921.22520.80680.026*
C22A0.7118 (3)1.1178 (2)0.86038 (14)0.0237 (6)
H22A0.63931.05590.84600.028*
H22B0.79431.09230.86930.028*
C23A0.7074 (3)1.1910 (2)0.93228 (15)0.0248 (6)
O1B1.0145 (2)1.00042 (15)0.91661 (11)0.0400 (5)
O2B0.9862 (2)0.85927 (15)0.95987 (11)0.0336 (5)
H2P0.980 (3)0.906 (2)0.9987 (14)0.050*
C1B1.0025 (2)0.7018 (2)0.43238 (15)0.0218 (6)
C2B1.0249 (2)0.6030 (2)0.43784 (15)0.0237 (6)
H2B1.03650.58800.48530.028*
C3B1.0308 (2)0.5264 (2)0.37656 (15)0.0236 (6)
H3B1.04650.46020.38260.028*
C4B1.0140 (2)0.5448 (2)0.30571 (15)0.0215 (6)
C5B1.0173 (3)0.4662 (2)0.24065 (15)0.0256 (6)
H5B1.02970.39870.24540.031*
C6B1.0032 (3)0.4859 (2)0.17310 (16)0.0274 (6)
H6B1.00570.43200.13110.033*
C7B0.9844 (2)0.5867 (2)0.16315 (15)0.0235 (6)
C8B0.9707 (3)0.6100 (2)0.09403 (16)0.0311 (7)
H8B0.97380.55750.05140.037*
C9B0.9528 (3)0.7079 (2)0.08623 (16)0.0310 (7)
H9B0.94380.72190.03860.037*
C10B0.9478 (3)0.7860 (2)0.14783 (15)0.0269 (6)
H10B0.93520.85300.14190.032*
C11B0.9612 (2)0.7668 (2)0.21823 (15)0.0226 (6)
C12B0.9575 (3)0.8450 (2)0.28320 (15)0.0245 (6)
H12B0.94580.91270.27850.029*
C13B0.9702 (2)0.8255 (2)0.35100 (15)0.0234 (6)
H13B0.96710.87970.39260.028*
C14B0.9885 (2)0.7246 (2)0.36191 (15)0.0203 (6)
C15B0.9934 (2)0.6457 (2)0.29844 (14)0.0193 (6)
C16B0.9798 (2)0.6661 (2)0.22665 (14)0.0198 (6)
C17B0.9926 (3)0.7791 (2)0.49945 (16)0.0309 (7)
H17B0.95860.83810.49010.037*
C18B1.0226 (4)0.7777 (3)0.56672 (18)0.0535 (10)
H18B1.05830.71930.57580.064*
C19B1.0111 (3)0.8540 (2)0.63549 (16)0.0334 (7)
H19C0.92910.87920.62290.040*
H19D1.08430.91570.65130.040*
C20B1.0123 (3)0.8049 (2)0.70078 (15)0.0267 (6)
H20C0.93570.74600.68590.032*
H20D1.09140.77520.71090.032*
C21B1.0097 (3)0.8827 (2)0.77258 (14)0.0251 (6)
H21C0.93100.91290.76260.030*
H21D1.08680.94120.78800.030*
C22B1.0095 (3)0.8319 (2)0.83661 (15)0.0259 (6)
H22C0.93380.77210.82040.031*
H22D1.08940.80320.84710.031*
C23B1.0035 (3)0.9059 (2)0.90779 (15)0.0260 (6)
O1C0.6907 (2)0.28109 (14)0.10986 (11)0.0331 (5)
O2C0.6698 (2)0.41463 (15)0.05805 (11)0.0333 (5)
H2Q0.686 (3)0.371 (2)0.0220 (15)0.050*
C1C0.6603 (2)0.5787 (2)0.58619 (15)0.0215 (6)
C2C0.6594 (3)0.6831 (2)0.58354 (15)0.0244 (6)
H2C0.65840.70030.53750.029*
C3C0.6598 (3)0.7614 (2)0.64555 (15)0.0253 (6)
H3C0.65840.83090.64140.030*
C4C0.6622 (2)0.7396 (2)0.71438 (15)0.0221 (6)
C5C0.6637 (3)0.8190 (2)0.78027 (15)0.0249 (6)
H5C0.66150.88870.77700.030*
C6C0.6683 (3)0.7973 (2)0.84681 (15)0.0252 (6)
H6C0.67010.85200.88940.030*
C7C0.6705 (3)0.6923 (2)0.85436 (15)0.0241 (6)
C8C0.6765 (3)0.6669 (2)0.92237 (15)0.0283 (6)
H8C0.67990.72060.96590.034*
C9C0.6775 (3)0.5650 (2)0.92765 (16)0.0300 (7)
H9C0.68220.54970.97460.036*
C10C0.6719 (3)0.4855 (2)0.86485 (15)0.0276 (6)
H10C0.67220.41580.86890.033*
C11C0.6658 (2)0.5068 (2)0.79512 (15)0.0224 (6)
C12C0.6606 (3)0.4266 (2)0.72900 (15)0.0232 (6)
H12C0.65850.35620.73190.028*
C13C0.6589 (2)0.4486 (2)0.66270 (15)0.0226 (6)
H13C0.65630.39330.62030.027*
C14C0.6607 (2)0.5538 (2)0.65459 (14)0.0194 (6)
C15C0.6627 (2)0.63459 (19)0.71920 (14)0.0185 (5)
C16C0.6667 (2)0.6115 (2)0.78970 (14)0.0205 (6)
C17C0.6560 (3)0.4983 (2)0.51713 (15)0.0234 (6)
H17C0.61120.42860.51080.028*
C18C0.7091 (3)0.5148 (2)0.46341 (15)0.0239 (6)
H18C0.75730.58360.47070.029*
C19C0.6997 (3)0.4343 (2)0.39215 (14)0.0237 (6)
H19E0.62610.37500.38360.028*
H19F0.78050.40620.39770.028*
C20C0.6798 (2)0.47802 (19)0.32339 (14)0.0210 (6)
H20E0.59600.50170.31580.025*
H20F0.75020.54030.33330.025*
C21C0.6791 (3)0.3979 (2)0.25162 (14)0.0214 (6)
H21E0.76030.37080.26000.026*
H21F0.60500.33770.23960.026*
C22C0.6679 (3)0.4450 (2)0.18521 (14)0.0223 (6)
H22E0.58350.46730.17480.027*
H22F0.73790.50880.19930.027*
C23C0.6770 (3)0.3718 (2)0.11480 (15)0.0237 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0587 (14)0.0231 (11)0.0227 (11)0.0115 (9)0.0163 (10)0.0075 (9)
O2A0.0563 (14)0.0268 (11)0.0182 (11)0.0132 (10)0.0130 (10)0.0076 (9)
C1A0.0248 (14)0.0241 (14)0.0190 (14)0.0040 (11)0.0060 (11)0.0038 (12)
C2A0.0362 (16)0.0286 (15)0.0199 (15)0.0088 (12)0.0081 (12)0.0120 (13)
C3A0.0353 (16)0.0219 (14)0.0268 (16)0.0095 (12)0.0078 (13)0.0091 (13)
C4A0.0212 (14)0.0228 (14)0.0225 (15)0.0073 (11)0.0063 (11)0.0066 (12)
C5A0.0285 (15)0.0217 (14)0.0281 (16)0.0078 (11)0.0081 (12)0.0045 (12)
C6A0.0286 (15)0.0276 (15)0.0268 (16)0.0064 (12)0.0084 (12)0.0014 (13)
C7A0.0197 (13)0.0297 (15)0.0185 (14)0.0050 (11)0.0065 (11)0.0048 (12)
C8A0.0337 (16)0.0374 (17)0.0203 (15)0.0076 (13)0.0103 (12)0.0032 (13)
C9A0.0357 (17)0.0419 (18)0.0247 (16)0.0059 (13)0.0103 (13)0.0163 (14)
C10A0.0328 (16)0.0297 (15)0.0262 (16)0.0032 (12)0.0102 (13)0.0107 (13)
C11A0.0241 (14)0.0246 (14)0.0193 (14)0.0027 (11)0.0067 (11)0.0062 (12)
C12A0.0290 (15)0.0220 (14)0.0282 (16)0.0050 (11)0.0078 (12)0.0102 (13)
C13A0.0277 (15)0.0216 (14)0.0213 (15)0.0061 (11)0.0079 (12)0.0043 (12)
C14A0.0192 (13)0.0222 (13)0.0184 (14)0.0053 (10)0.0055 (11)0.0047 (11)
C15A0.0156 (13)0.0214 (13)0.0203 (14)0.0043 (10)0.0058 (10)0.0052 (11)
C16A0.0169 (13)0.0256 (14)0.0192 (14)0.0058 (10)0.0064 (11)0.0055 (12)
C17A0.0389 (17)0.0257 (15)0.0235 (16)0.0039 (12)0.0071 (13)0.0066 (13)
C18A0.0396 (17)0.0254 (15)0.0233 (16)0.0059 (12)0.0091 (13)0.0080 (13)
C19A0.0310 (15)0.0249 (14)0.0211 (15)0.0063 (12)0.0093 (12)0.0043 (12)
C20A0.0252 (14)0.0190 (13)0.0202 (14)0.0050 (10)0.0072 (11)0.0040 (11)
C21A0.0250 (14)0.0225 (13)0.0192 (14)0.0062 (11)0.0072 (11)0.0057 (12)
C22A0.0305 (15)0.0216 (13)0.0196 (14)0.0068 (11)0.0072 (12)0.0059 (12)
C23A0.0270 (15)0.0269 (15)0.0217 (15)0.0050 (11)0.0067 (12)0.0089 (12)
O1B0.0757 (16)0.0215 (11)0.0268 (12)0.0097 (10)0.0225 (11)0.0060 (9)
O2B0.0565 (14)0.0276 (11)0.0198 (11)0.0080 (10)0.0149 (10)0.0086 (9)
C1B0.0195 (13)0.0273 (14)0.0180 (14)0.0038 (11)0.0049 (11)0.0056 (12)
C2B0.0238 (14)0.0286 (15)0.0204 (15)0.0080 (11)0.0053 (11)0.0091 (12)
C3B0.0214 (14)0.0228 (14)0.0275 (16)0.0052 (11)0.0058 (12)0.0088 (12)
C4B0.0162 (13)0.0240 (14)0.0229 (15)0.0026 (10)0.0048 (11)0.0049 (12)
C5B0.0274 (15)0.0218 (14)0.0274 (16)0.0067 (11)0.0087 (12)0.0039 (12)
C6B0.0287 (15)0.0261 (15)0.0235 (16)0.0047 (12)0.0091 (12)−0.0021 (12)
C7B0.0200 (14)0.0271 (15)0.0206 (15)0.0010 (11)0.0068 (11)0.0024 (12)
C8B0.0336 (16)0.0350 (16)0.0206 (15)0.0020 (13)0.0081 (13)0.0021 (13)
C9B0.0345 (16)0.0401 (17)0.0199 (15)0.0040 (13)0.0072 (12)0.0134 (14)
C10B0.0280 (15)0.0291 (15)0.0253 (16)0.0038 (12)0.0070 (12)0.0126 (13)
C11B0.0212 (14)0.0235 (14)0.0234 (15)0.0022 (11)0.0056 (11)0.0087 (12)
C12B0.0276 (15)0.0212 (14)0.0267 (16)0.0064 (11)0.0081 (12)0.0089 (12)
C13B0.0235 (14)0.0233 (14)0.0230 (15)0.0059 (11)0.0069 (11)0.0042 (12)
C14B0.0168 (13)0.0228 (14)0.0194 (14)0.0038 (10)0.0030 (11)0.0041 (12)
C15B0.0141 (12)0.0227 (14)0.0202 (14)0.0025 (10)0.0050 (10)0.0048 (12)
C16B0.0175 (13)0.0242 (14)0.0165 (14)0.0014 (10)0.0054 (10)0.0040 (11)
C17B0.0482 (19)0.0283 (15)0.0240 (17)0.0186 (13)0.0136 (14)0.0117 (13)
C18B0.117 (3)0.0291 (17)0.0253 (19)0.0310 (19)0.0275 (19)0.0113 (15)
C19B0.054 (2)0.0273 (15)0.0196 (15)0.0114 (14)0.0116 (14)0.0049 (13)
C20B0.0342 (16)0.0261 (14)0.0199 (15)0.0077 (12)0.0054 (12)0.0076 (12)
C21B0.0305 (15)0.0245 (14)0.0193 (15)0.0050 (12)0.0069 (12)0.0042 (12)
C22B0.0310 (15)0.0261 (15)0.0221 (15)0.0084 (12)0.0074 (12)0.0075 (12)
C23B0.0307 (15)0.0267 (15)0.0207 (15)0.0039 (12)0.0072 (12)0.0074 (12)
O1C0.0585 (14)0.0228 (11)0.0225 (11)0.0117 (9)0.0162 (10)0.0077 (9)
O2C0.0568 (14)0.0284 (11)0.0212 (11)0.0152 (10)0.0163 (10)0.0098 (9)
C1C0.0195 (13)0.0235 (14)0.0207 (15)0.0039 (11)0.0054 (11)0.0049 (12)
C2C0.0293 (15)0.0260 (14)0.0201 (15)0.0060 (11)0.0073 (12)0.0094 (12)
C3C0.0311 (15)0.0202 (14)0.0262 (16)0.0068 (11)0.0092 (12)0.0070 (12)
C4C0.0242 (14)0.0202 (13)0.0231 (15)0.0062 (11)0.0068 (11)0.0069 (12)
C5C0.0278 (15)0.0199 (14)0.0269 (16)0.0073 (11)0.0082 (12)0.0040 (12)
C6C0.0275 (15)0.0231 (14)0.0235 (15)0.0067 (11)0.0085 (12)0.0008 (12)
C7C0.0240 (14)0.0264 (14)0.0215 (15)0.0048 (11)0.0069 (11)0.0054 (12)
C8C0.0334 (16)0.0340 (16)0.0160 (14)0.0065 (12)0.0078 (12)0.0032 (12)
C9C0.0331 (16)0.0394 (17)0.0178 (15)0.0062 (13)0.0050 (12)0.0114 (13)
C10C0.0330 (16)0.0300 (15)0.0236 (16)0.0083 (12)0.0095 (12)0.0120 (13)
C11C0.0212 (14)0.0252 (14)0.0228 (15)0.0054 (11)0.0070 (11)0.0093 (12)
C12C0.0274 (15)0.0203 (13)0.0234 (15)0.0062 (11)0.0085 (12)0.0067 (12)
C13C0.0268 (14)0.0183 (13)0.0217 (15)0.0052 (11)0.0088 (12)0.0009 (11)
C14C0.0175 (13)0.0239 (13)0.0175 (14)0.0033 (10)0.0062 (11)0.0063 (11)
C15C0.0168 (13)0.0206 (13)0.0171 (14)0.0026 (10)0.0043 (10)0.0043 (11)
C16C0.0176 (13)0.0242 (14)0.0193 (14)0.0039 (11)0.0049 (11)0.0054 (12)
C17C0.0265 (15)0.0229 (14)0.0201 (15)0.0055 (11)0.0049 (11)0.0057 (12)
C18C0.0277 (15)0.0216 (13)0.0208 (15)0.0044 (11)0.0056 (12)0.0040 (11)
C19C0.0298 (15)0.0239 (14)0.0194 (14)0.0081 (11)0.0085 (12)0.0062 (12)
C20C0.0234 (14)0.0218 (13)0.0188 (14)0.0054 (11)0.0070 (11)0.0057 (11)
C21C0.0230 (14)0.0229 (13)0.0179 (14)0.0059 (11)0.0048 (11)0.0050 (11)
C22C0.0264 (14)0.0231 (14)0.0177 (14)0.0050 (11)0.0071 (11)0.0050 (12)
C23C0.0264 (14)0.0255 (15)0.0183 (14)0.0030 (11)0.0054 (11)0.0063 (12)

Geometric parameters (Å, °)

O1A—C23A1.224 (3)C11B—C16B1.425 (4)
O2A—C23A1.319 (3)C11B—C12B1.432 (4)
O2A—H2O0.875 (18)C12B—C13B1.350 (4)
C1A—C2A1.398 (4)C12B—H12B0.9500
C1A—C14A1.416 (4)C13B—C14B1.441 (3)
C1A—C17A1.472 (4)C13B—H13B0.9500
C2A—C3A1.380 (4)C14B—C15B1.422 (4)
C2A—H2A0.9500C15B—C16B1.428 (3)
C3A—C4A1.399 (4)C17B—C18B1.248 (4)
C3A—H3A0.9500C17B—H17B0.9500
C4A—C5A1.431 (4)C18B—C19B1.500 (4)
C4A—C15A1.431 (3)C18B—H18B0.9500
C5A—C6A1.352 (4)C19B—C20B1.526 (4)
C5A—H5A0.9500C19B—H19C0.9900
C6A—C7A1.434 (4)C19B—H19D0.9900
C6A—H6A0.9500C20B—C21B1.519 (4)
C7A—C8A1.398 (4)C20B—H20C0.9900
C7A—C16A1.423 (4)C20B—H20D0.9900
C8A—C9A1.391 (4)C21B—C22B1.520 (3)
C8A—H8A0.9500C21B—H21C0.9900
C9A—C10A1.383 (4)C21B—H21D0.9900
C9A—H9A0.9500C22B—C23B1.498 (4)
C10A—C11A1.399 (4)C22B—H22C0.9900
C10A—H10A0.9500C22B—H22D0.9900
C11A—C16A1.420 (3)O1C—C23C1.224 (3)
C11A—C12A1.437 (4)O2C—C23C1.322 (3)
C12A—C13A1.353 (4)O2C—H2Q0.859 (18)
C12A—H12A0.9500C1C—C2C1.405 (4)
C13A—C14A1.435 (3)C1C—C14C1.410 (3)
C13A—H13A0.9500C1C—C17C1.476 (4)
C14A—C15A1.419 (4)C2C—C3C1.380 (4)
C15A—C16A1.428 (4)C2C—H2C0.9500
C17A—C18A1.304 (4)C3C—C4C1.396 (4)
C17A—H17A0.9500C3C—H3C0.9500
C18A—C19A1.497 (4)C4C—C15C1.424 (3)
C18A—H18A0.9500C4C—C5C1.435 (4)
C19A—C20A1.531 (3)C5C—C6C1.350 (4)
C19A—H19A0.9900C5C—H5C0.9500
C19A—H19B0.9900C6C—C7C1.442 (4)
C20A—C21A1.526 (4)C6C—H6C0.9500
C20A—H20A0.9900C7C—C8C1.397 (4)
C20A—H20B0.9900C7C—C16C1.423 (4)
C21A—C22A1.527 (3)C8C—C9C1.387 (4)
C21A—H21A0.9900C8C—H8C0.9500
C21A—H21B0.9900C9C—C10C1.383 (4)
C22A—C23A1.498 (4)C9C—H9C0.9500
C22A—H22A0.9900C10C—C11C1.404 (4)
C22A—H22B0.9900C10C—H10C0.9500
O1B—C23B1.217 (3)C11C—C16C1.421 (3)
O2B—C23B1.314 (3)C11C—C12C1.433 (4)
O2B—H2P0.872 (18)C12C—C13C1.351 (4)
C1B—C2B1.396 (4)C12C—H12C0.9500
C1B—C14B1.417 (4)C13C—C14C1.444 (3)
C1B—C17B1.477 (4)C13C—H13C0.9500
C2B—C3B1.379 (4)C14C—C15C1.427 (4)
C2B—H2B0.9500C15C—C16C1.432 (3)
C3B—C4B1.397 (4)C17C—C18C1.320 (4)
C3B—H3B0.9500C17C—H17C0.9500
C4B—C15B1.426 (4)C18C—C19C1.492 (4)
C4B—C5B1.434 (4)C18C—H18C0.9500
C5B—C6B1.345 (4)C19C—C20C1.531 (3)
C5B—H5B0.9500C19C—H19E0.9900
C6B—C7B1.435 (4)C19C—H19F0.9900
C6B—H6B0.9500C20C—C21C1.522 (4)
C7B—C8B1.396 (4)C20C—H20E0.9900
C7B—C16B1.424 (4)C20C—H20F0.9900
C8B—C9B1.383 (4)C21C—C22C1.520 (3)
C8B—H8B0.9500C21C—H21E0.9900
C9B—C10B1.391 (4)C21C—H21F0.9900
C9B—H9B0.9500C22C—C23C1.494 (4)
C10B—C11B1.396 (4)C22C—H22E0.9900
C10B—H10B0.9500C22C—H22F0.9900
C23A—O2A—H2O110 (2)C1B—C14B—C13B123.1 (2)
C2A—C1A—C14A118.5 (2)C15B—C14B—C13B117.5 (2)
C2A—C1A—C17A119.6 (2)C14B—C15B—C4B120.4 (2)
C14A—C1A—C17A121.9 (2)C14B—C15B—C16B120.8 (2)
C3A—C2A—C1A122.4 (2)C4B—C15B—C16B118.8 (2)
C3A—C2A—H2A118.8C7B—C16B—C11B119.5 (2)
C1A—C2A—H2A118.8C7B—C16B—C15B120.6 (2)
C2A—C3A—C4A120.8 (2)C11B—C16B—C15B119.8 (2)
C2A—C3A—H3A119.6C18B—C17B—C1B129.0 (3)
C4A—C3A—H3A119.6C18B—C17B—H17B115.5
C3A—C4A—C5A122.6 (2)C1B—C17B—H17B115.5
C3A—C4A—C15A118.2 (2)C17B—C18B—C19B130.0 (3)
C5A—C4A—C15A119.2 (2)C17B—C18B—H18B115.0
C6A—C5A—C4A121.7 (2)C19B—C18B—H18B115.0
C6A—C5A—H5A119.1C18B—C19B—C20B112.4 (2)
C4A—C5A—H5A119.1C18B—C19B—H19C109.1
C5A—C6A—C7A120.9 (3)C20B—C19B—H19C109.1
C5A—C6A—H6A119.5C18B—C19B—H19D109.1
C7A—C6A—H6A119.5C20B—C19B—H19D109.1
C8A—C7A—C16A118.6 (2)H19C—C19B—H19D107.9
C8A—C7A—C6A122.7 (3)C21B—C20B—C19B113.2 (2)
C16A—C7A—C6A118.7 (2)C21B—C20B—H20C108.9
C9A—C8A—C7A121.3 (3)C19B—C20B—H20C108.9
C9A—C8A—H8A119.3C21B—C20B—H20D108.9
C7A—C8A—H8A119.3C19B—C20B—H20D108.9
C10A—C9A—C8A120.5 (3)H20C—C20B—H20D107.7
C10A—C9A—H9A119.8C20B—C21B—C22B112.3 (2)
C8A—C9A—H9A119.8C20B—C21B—H21C109.1
C9A—C10A—C11A120.2 (3)C22B—C21B—H21C109.1
C9A—C10A—H10A119.9C20B—C21B—H21D109.1
C11A—C10A—H10A119.9C22B—C21B—H21D109.1
C10A—C11A—C16A119.9 (2)H21C—C21B—H21D107.9
C10A—C11A—C12A122.0 (2)C23B—C22B—C21B113.8 (2)
C16A—C11A—C12A118.1 (2)C23B—C22B—H22C108.8
C13A—C12A—C11A121.8 (2)C21B—C22B—H22C108.8
C13A—C12A—H12A119.1C23B—C22B—H22D108.8
C11A—C12A—H12A119.1C21B—C22B—H22D108.8
C12A—C13A—C14A121.5 (2)H22C—C22B—H22D107.7
C12A—C13A—H13A119.2O1B—C23B—O2B123.2 (3)
C14A—C13A—H13A119.2O1B—C23B—C22B123.0 (2)
C1A—C14A—C15A119.6 (2)O2B—C23B—C22B113.8 (2)
C1A—C14A—C13A122.6 (2)C23C—O2C—H2Q107 (2)
C15A—C14A—C13A117.8 (2)C2C—C1C—C14C118.4 (2)
C14A—C15A—C16A120.8 (2)C2C—C1C—C17C119.3 (2)
C14A—C15A—C4A120.5 (2)C14C—C1C—C17C122.2 (2)
C16A—C15A—C4A118.7 (2)C3C—C2C—C1C122.2 (2)
C11A—C16A—C7A119.6 (2)C3C—C2C—H2C118.9
C11A—C16A—C15A119.8 (2)C1C—C2C—H2C118.9
C7A—C16A—C15A120.7 (2)C2C—C3C—C4C120.7 (2)
C18A—C17A—C1A126.0 (3)C2C—C3C—H3C119.7
C18A—C17A—H17A117.0C4C—C3C—H3C119.7
C1A—C17A—H17A117.0C3C—C4C—C15C118.7 (2)
C17A—C18A—C19A127.7 (3)C3C—C4C—C5C122.4 (2)
C17A—C18A—H18A116.1C15C—C4C—C5C118.9 (2)
C19A—C18A—H18A116.1C6C—C5C—C4C121.8 (2)
C18A—C19A—C20A112.7 (2)C6C—C5C—H5C119.1
C18A—C19A—H19A109.0C4C—C5C—H5C119.1
C20A—C19A—H19A109.0C5C—C6C—C7C121.1 (2)
C18A—C19A—H19B109.0C5C—C6C—H6C119.5
C20A—C19A—H19B109.0C7C—C6C—H6C119.5
H19A—C19A—H19B107.8C8C—C7C—C16C118.7 (2)
C21A—C20A—C19A112.9 (2)C8C—C7C—C6C122.8 (2)
C21A—C20A—H20A109.0C16C—C7C—C6C118.4 (2)
C19A—C20A—H20A109.0C9C—C8C—C7C121.4 (3)
C21A—C20A—H20B109.0C9C—C8C—H8C119.3
C19A—C20A—H20B109.0C7C—C8C—H8C119.3
H20A—C20A—H20B107.8C10C—C9C—C8C120.3 (3)
C20A—C21A—C22A111.9 (2)C10C—C9C—H9C119.9
C20A—C21A—H21A109.2C8C—C9C—H9C119.9
C22A—C21A—H21A109.2C9C—C10C—C11C120.6 (3)
C20A—C21A—H21B109.2C9C—C10C—H10C119.7
C22A—C21A—H21B109.2C11C—C10C—H10C119.7
H21A—C21A—H21B107.9C10C—C11C—C16C119.3 (2)
C23A—C22A—C21A114.2 (2)C10C—C11C—C12C122.1 (2)
C23A—C22A—H22A108.7C16C—C11C—C12C118.5 (2)
C21A—C22A—H22A108.7C13C—C12C—C11C121.7 (2)
C23A—C22A—H22B108.7C13C—C12C—H12C119.2
C21A—C22A—H22B108.7C11C—C12C—H12C119.2
H22A—C22A—H22B107.6C12C—C13C—C14C121.8 (2)
O1A—C23A—O2A123.1 (3)C12C—C13C—H13C119.1
O1A—C23A—C22A123.5 (2)C14C—C13C—H13C119.1
O2A—C23A—C22A113.5 (2)C1C—C14C—C15C119.7 (2)
C23B—O2B—H2P109 (2)C1C—C14C—C13C122.7 (2)
C2B—C1B—C14B118.7 (2)C15C—C14C—C13C117.6 (2)
C2B—C1B—C17B119.5 (2)C4C—C15C—C14C120.2 (2)
C14B—C1B—C17B121.8 (2)C4C—C15C—C16C119.3 (2)
C3B—C2B—C1B122.1 (2)C14C—C15C—C16C120.5 (2)
C3B—C2B—H2B119.0C11C—C16C—C7C119.6 (2)
C1B—C2B—H2B119.0C11C—C16C—C15C119.9 (2)
C2B—C3B—C4B121.0 (2)C7C—C16C—C15C120.5 (2)
C2B—C3B—H3B119.5C18C—C17C—C1C125.7 (2)
C4B—C3B—H3B119.5C18C—C17C—H17C117.2
C3B—C4B—C15B118.4 (2)C1C—C17C—H17C117.2
C3B—C4B—C5B122.3 (2)C17C—C18C—C19C125.5 (2)
C15B—C4B—C5B119.3 (2)C17C—C18C—H18C117.2
C6B—C5B—C4B121.5 (2)C19C—C18C—H18C117.2
C6B—C5B—H5B119.2C18C—C19C—C20C113.1 (2)
C4B—C5B—H5B119.2C18C—C19C—H19E109.0
C5B—C6B—C7B121.3 (3)C20C—C19C—H19E109.0
C5B—C6B—H6B119.3C18C—C19C—H19F109.0
C7B—C6B—H6B119.3C20C—C19C—H19F109.0
C8B—C7B—C16B118.8 (2)H19E—C19C—H19F107.8
C8B—C7B—C6B122.8 (3)C21C—C20C—C19C113.1 (2)
C16B—C7B—C6B118.4 (2)C21C—C20C—H20E109.0
C9B—C8B—C7B121.4 (3)C19C—C20C—H20E109.0
C9B—C8B—H8B119.3C21C—C20C—H20F109.0
C7B—C8B—H8B119.3C19C—C20C—H20F109.0
C8B—C9B—C10B120.3 (3)H20E—C20C—H20F107.8
C8B—C9B—H9B119.9C22C—C21C—C20C112.2 (2)
C10B—C9B—H9B119.9C22C—C21C—H21E109.2
C9B—C10B—C11B120.6 (3)C20C—C21C—H21E109.2
C9B—C10B—H10B119.7C22C—C21C—H21F109.2
C11B—C10B—H10B119.7C20C—C21C—H21F109.2
C10B—C11B—C16B119.4 (2)H21E—C21C—H21F107.9
C10B—C11B—C12B122.4 (2)C23C—C22C—C21C114.2 (2)
C16B—C11B—C12B118.2 (2)C23C—C22C—H22E108.7
C13B—C12B—C11B121.9 (2)C21C—C22C—H22E108.7
C13B—C12B—H12B119.0C23C—C22C—H22F108.7
C11B—C12B—H12B119.0C21C—C22C—H22F108.7
C12B—C13B—C14B121.7 (2)H22E—C22C—H22F107.6
C12B—C13B—H13B119.1O1C—C23C—O2C122.9 (2)
C14B—C13B—H13B119.1O1C—C23C—C22C123.6 (2)
C1B—C14B—C15B119.4 (2)O2C—C23C—C22C113.5 (2)
C14A—C1A—C2A—C3A0.2 (4)C1B—C14B—C15B—C16B−179.9 (2)
C17A—C1A—C2A—C3A−178.7 (3)C13B—C14B—C15B—C16B−0.4 (3)
C1A—C2A—C3A—C4A1.3 (4)C3B—C4B—C15B—C14B−0.8 (4)
C2A—C3A—C4A—C5A178.1 (3)C5B—C4B—C15B—C14B179.4 (2)
C2A—C3A—C4A—C15A−0.8 (4)C3B—C4B—C15B—C16B178.3 (2)
C3A—C4A—C5A—C6A−177.6 (3)C5B—C4B—C15B—C16B−1.5 (3)
C15A—C4A—C5A—C6A1.2 (4)C8B—C7B—C16B—C11B0.2 (4)
C4A—C5A—C6A—C7A−0.9 (4)C6B—C7B—C16B—C11B−180.0 (2)
C5A—C6A—C7A—C8A−179.8 (3)C8B—C7B—C16B—C15B−180.0 (2)
C5A—C6A—C7A—C16A−0.8 (4)C6B—C7B—C16B—C15B−0.1 (4)
C16A—C7A—C8A—C9A−0.2 (4)C10B—C11B—C16B—C7B0.0 (4)
C6A—C7A—C8A—C9A178.8 (3)C12B—C11B—C16B—C7B−179.8 (2)
C7A—C8A—C9A—C10A−1.3 (4)C10B—C11B—C16B—C15B−179.9 (2)
C8A—C9A—C10A—C11A1.9 (4)C12B—C11B—C16B—C15B0.4 (3)
C9A—C10A—C11A—C16A−0.8 (4)C14B—C15B—C16B—C7B−179.8 (2)
C9A—C10A—C11A—C12A−179.3 (3)C4B—C15B—C16B—C7B1.1 (3)
C10A—C11A—C12A—C13A−178.2 (3)C14B—C15B—C16B—C11B0.1 (3)
C16A—C11A—C12A—C13A3.3 (4)C4B—C15B—C16B—C11B−179.0 (2)
C11A—C12A—C13A—C14A−0.6 (4)C2B—C1B—C17B—C18B13.3 (5)
C2A—C1A—C14A—C15A−2.1 (4)C14B—C1B—C17B—C18B−167.4 (4)
C17A—C1A—C14A—C15A176.8 (2)C1B—C17B—C18B—C19B−178.6 (3)
C2A—C1A—C14A—C13A176.0 (2)C17B—C18B—C19B—C20B159.4 (4)
C17A—C1A—C14A—C13A−5.1 (4)C18B—C19B—C20B—C21B176.2 (3)
C12A—C13A—C14A—C1A178.7 (3)C19B—C20B—C21B—C22B179.4 (2)
C12A—C13A—C14A—C15A−3.2 (4)C20B—C21B—C22B—C23B−178.5 (2)
C1A—C14A—C15A—C16A−177.5 (2)C21B—C22B—C23B—O1B−8.9 (4)
C13A—C14A—C15A—C16A4.2 (4)C21B—C22B—C23B—O2B171.5 (2)
C1A—C14A—C15A—C4A2.7 (4)C14C—C1C—C2C—C3C0.5 (4)
C13A—C14A—C15A—C4A−175.6 (2)C17C—C1C—C2C—C3C178.3 (2)
C3A—C4A—C15A—C14A−1.2 (4)C1C—C2C—C3C—C4C0.5 (4)
C5A—C4A—C15A—C14A179.9 (2)C2C—C3C—C4C—C15C−0.7 (4)
C3A—C4A—C15A—C16A179.0 (2)C2C—C3C—C4C—C5C179.5 (2)
C5A—C4A—C15A—C16A0.1 (4)C3C—C4C—C5C—C6C−178.8 (3)
C10A—C11A—C16A—C7A−0.8 (4)C15C—C4C—C5C—C6C1.4 (4)
C12A—C11A—C16A—C7A177.8 (2)C4C—C5C—C6C—C7C−0.6 (4)
C10A—C11A—C16A—C15A179.3 (2)C5C—C6C—C7C—C8C179.3 (3)
C12A—C11A—C16A—C15A−2.1 (4)C5C—C6C—C7C—C16C−0.5 (4)
C8A—C7A—C16A—C11A1.3 (4)C16C—C7C—C8C—C9C−0.6 (4)
C6A—C7A—C16A—C11A−177.8 (2)C6C—C7C—C8C—C9C179.6 (3)
C8A—C7A—C16A—C15A−178.8 (2)C7C—C8C—C9C—C10C−0.3 (4)
C6A—C7A—C16A—C15A2.1 (4)C8C—C9C—C10C—C11C0.4 (4)
C14A—C15A—C16A—C11A−1.6 (4)C9C—C10C—C11C—C16C0.6 (4)
C4A—C15A—C16A—C11A178.2 (2)C9C—C10C—C11C—C12C179.6 (3)
C14A—C15A—C16A—C7A178.5 (2)C10C—C11C—C12C—C13C−177.9 (3)
C4A—C15A—C16A—C7A−1.7 (4)C16C—C11C—C12C—C13C1.1 (4)
C2A—C1A—C17A—C18A−35.6 (4)C11C—C12C—C13C—C14C−0.6 (4)
C14A—C1A—C17A—C18A145.6 (3)C2C—C1C—C14C—C15C−1.2 (4)
C1A—C17A—C18A—C19A179.0 (3)C17C—C1C—C14C—C15C−178.9 (2)
C17A—C18A—C19A—C20A−143.0 (3)C2C—C1C—C14C—C13C178.7 (2)
C18A—C19A—C20A—C21A−173.9 (2)C17C—C1C—C14C—C13C0.9 (4)
C19A—C20A—C21A—C22A176.3 (2)C12C—C13C—C14C—C1C179.3 (2)
C20A—C21A—C22A—C23A−175.2 (2)C12C—C13C—C14C—C15C−0.8 (4)
C21A—C22A—C23A—O1A−2.3 (4)C3C—C4C—C15C—C14C0.0 (4)
C21A—C22A—C23A—O2A176.7 (2)C5C—C4C—C15C—C14C179.8 (2)
C14B—C1B—C2B—C3B−1.5 (4)C3C—C4C—C15C—C16C179.3 (2)
C17B—C1B—C2B—C3B177.8 (2)C5C—C4C—C15C—C16C−0.9 (4)
C1B—C2B—C3B—C4B−0.2 (4)C1C—C14C—C15C—C4C1.0 (4)
C2B—C3B—C4B—C15B1.4 (4)C13C—C14C—C15C—C4C−178.9 (2)
C2B—C3B—C4B—C5B−178.9 (2)C1C—C14C—C15C—C16C−178.3 (2)
C3B—C4B—C5B—C6B−178.8 (3)C13C—C14C—C15C—C16C1.8 (3)
C15B—C4B—C5B—C6B0.9 (4)C10C—C11C—C16C—C7C−1.6 (4)
C4B—C5B—C6B—C7B0.1 (4)C12C—C11C—C16C—C7C179.4 (2)
C5B—C6B—C7B—C8B179.3 (3)C10C—C11C—C16C—C15C178.9 (2)
C5B—C6B—C7B—C16B−0.5 (4)C12C—C11C—C16C—C15C−0.1 (4)
C16B—C7B—C8B—C9B−0.1 (4)C8C—C7C—C16C—C11C1.6 (4)
C6B—C7B—C8B—C9B−180.0 (3)C6C—C7C—C16C—C11C−178.6 (2)
C7B—C8B—C9B—C10B−0.1 (4)C8C—C7C—C16C—C15C−178.9 (2)
C8B—C9B—C10B—C11B0.2 (4)C6C—C7C—C16C—C15C0.9 (4)
C9B—C10B—C11B—C16B−0.1 (4)C4C—C15C—C16C—C11C179.3 (2)
C9B—C10B—C11B—C12B179.6 (3)C14C—C15C—C16C—C11C−1.4 (4)
C10B—C11B—C12B—C13B179.8 (3)C4C—C15C—C16C—C7C−0.2 (4)
C16B—C11B—C12B—C13B−0.5 (4)C14C—C15C—C16C—C7C179.1 (2)
C11B—C12B—C13B—C14B0.1 (4)C2C—C1C—C17C—C18C33.4 (4)
C2B—C1B—C14B—C15B2.0 (4)C14C—C1C—C17C—C18C−148.9 (3)
C17B—C1B—C14B—C15B−177.4 (2)C1C—C17C—C18C—C19C−177.2 (2)
C2B—C1B—C14B—C13B−177.5 (2)C17C—C18C—C19C—C20C139.5 (3)
C17B—C1B—C14B—C13B3.2 (4)C18C—C19C—C20C—C21C176.3 (2)
C12B—C13B—C14B—C1B179.8 (2)C19C—C20C—C21C—C22C−176.3 (2)
C12B—C13B—C14B—C15B0.3 (4)C20C—C21C—C22C—C23C175.6 (2)
C1B—C14B—C15B—C4B−0.8 (4)C21C—C22C—C23C—O1C0.8 (4)
C13B—C14B—C15B—C4B178.7 (2)C21C—C22C—C23C—O2C−178.7 (2)

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1A–C4A,C15A,C14A and C7C–C11C,C16C rings, respectively.
D—H···AD—HH···AD···AD—H···A
O2A—H2O···O1Ci0.88 (2)1.79 (2)2.661 (3)177 (3)
O2B—H2P···O1Bii0.87 (2)1.78 (2)2.642 (3)173 (3)
O2C—H2Q···O1Aiii0.86 (2)1.78 (2)2.636 (3)172 (3)
C10C—H10C···O1Aiv0.952.463.336 (3)154
C10B—H10B···O1Bv0.952.513.354 (3)148
C10A—H10A···O1Cvi0.952.513.360 (3)150
C22C—H22E···Cg2vii0.992.633.500 (4)147
C19A—H19A···Cg1viii0.992.723.511 (4)137

Symmetry codes: (i) x, y+1, z+1; (ii) −x+2, −y+2, −z+2; (iii) x, y−1, z−1; (iv) x, y−1, z; (v) −x+2, −y+2, −z+1; (vi) x, y+1, z; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2323).

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