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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1623–o1624.
Published online 2009 June 20. doi:  10.1107/S1600536809022739
PMCID: PMC2969353

4-(9-Anthr­yl)-1-(2,4-dimethoxy­phen­yl)spiro­[azetidine-3,9′-xanthen]-2-one

Abstract

The title compound, C37H27NO4, crystallizes with two mol­ecules in the asymmetric unit. The β-lactam ring of each mol­ecule is very nearly planar, with maximum deviations of 0.001 (2) and 0.017 (2) Å in the two mol­ecules. The crystal structure is stabilized by inter­molecular C—H(...)O and C—H(...)N contacts, as well as by weak C—H(...)π inter­actions.

Related literature

For the biological properties of spiro-β-lactams, see: Kobayashi et al. (1991 [triangle]); Sheehan et al. (1978 [triangle]); Skiles & McNeil (1990 [triangle]); Waldmann (1995 [triangle]). For polycyclic aromatic β-lactams with anti-cancer activity, see: Banik et al. (2003 [triangle], 2004 [triangle]); Becker & Banik (1998 [triangle]). For several syntheses of spiro-β-lactams, see: Jarrahpoor & Khalili (2007 [triangle]). For the structural characterizations of some β-lactam compounds, see: Akkurt et al. (2008a [triangle],b [triangle]); Yalçın et al. (2009 [triangle]). For ring puckering analysis, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1623-scheme1.jpg

Experimental

Crystal data

  • C37H27NO4
  • M r = 549.60
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1623-efi1.jpg
  • a = 12.3164 (6) Å
  • b = 13.1277 (7) Å
  • c = 18.4838 (11) Å
  • α = 92.434 (5)°
  • β = 109.236 (4)°
  • γ = 91.357 (4)°
  • V = 2816.9 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 295 K
  • 0.35 × 0.32 × 0.28 mm

Data collection

  • Stoe IPDS 2 diffractometer
  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002 [triangle]) T min = 0.971, T max = 0.977
  • 30264 measured reflections
  • 11851 independent reflections
  • 6076 reflections with I > 2σ(I)
  • R int = 0.100

Refinement

  • R[F 2 > 2σ(F 2)] = 0.057
  • wR(F 2) = 0.131
  • S = 0.88
  • 11851 reflections
  • 762 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 [triangle]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022739/tk2470sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022739/tk2470Isup2.hkl

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

supplementary crystallographic information

Comment

Spiro compounds represent an important class of naturally occurring compounds characterized by pronounced biological properties (Kobayashi et al., 1991; Waldmann, 1995). Spiro-β-lactams are also interesting due to their anti-viral (Skiles & McNeil, 1990) and anti-bacterial properties (Sheehan et al., 1978). Several syntheses of spiro-β-lactams are available in the literature (Jarrahpoor & Khalili, 2007). Some polycyclic aromatic β-lactams with anti-cancer effects have also been reported (Banik et al., 2003 & 2004; Becker & Banik, 1998). As an extension of our work (Yalçın et al., 2009; Akkurt et al., 2008a,b) on structural characterization of the β-lactam compounds, the title compound, (I), is reported herein.

The asymmetric unit of (I) contains two enantiomorphic molecules IA and IB (Fig. 1 for molecule IA and Fig. 2 for molecule IB) and there is one chiral centre in each molecule, i.e. at C15, which have S and R configurations. In (I), the bond lengths and angles are comparable with the values found in related structures (Yalçın et al., 2009; Akkurt et al., 2008a,b). The β-lactam units of molecules IA and IB are very nearly planar, with maximum deviations of 0.001 (2) Å and -0.017 (2) Å, respectively, from the respective least-squares plane. The dihedral angles between the planes in molecules IA and IB are given in Table 2, and those between the similar planes of the molecules IA and IB are given in Table 3.

In the xanthene ring systems, the central ring, [O1/C16/C17/C22/C23/C28 for molecule IA, and O1'/C16'/C17'/C22'/C23'/C28' for molecule IB] is not planar, with puckering parameters: QT= 0.417 (3) Å, θ = 98.2 (4)° and [var phi] = 4.8 (4)° for molecule IA and QT= 0.357 (2) Å, θ = 81.1 (3)° and [var phi] = 185.9 (4)° for molecule IB (Cremer & Pople, 1975).

The anthracene ring systems, attached at C15 for molecule IA and C15' for molecule IB, are almost planar, with significant deviations of -0.068 (4) Å for C3, 0.050 (3) Å for C6, and -0.052 (3) Å for C10 in molecule IA, and with significant deviations of -0.040 (3) Å for C6', 0.043 (3) Å for C11', and -0.075 (2) Å for C14' in molecule IB.

The molecular conformation is stabilized by intramolecular C—H···O and C—H···N contacts. Molecules are linked to each other by intermolecular C—H···O and C—H···N contacts and by weak C—H···π interactions (Table 1).

Experimental

A mixture of the Schiff base (E)—N-(anthracen-9-ylmethylene)-2,4-dimethoxybenzamine (0.30 g, 0.87 mmol) and triethylamine (0.44 g, 4.39 mmol), 9H-xanthen-9-carboxylic acid (0.30 g,1.31 mmol) and tosyl chloride (0.25 g, 1.31 mmol) in CH2Cl2 (15 ml) was stirred at room temperature for 24 h. The solution was washed with HCl (1 N, 20 ml), a saturated sodium bicarbonate solution (20 ml), and then brine (20 ml). It was then dried over Na2SO4. The solvent was evaporated to give the crude product as a light-green crystalline material which was then purified by recrystallization from ethylacetate [yield 69%, m.p. 453–455 K]. IR (KBr, cm-1): 1739 (CO β-lactam). 1H-NMR δ (p.p.m.): 2.91, 3.58 (s, 6H, 2OMe) 6.16 (s, 1H, 4), 6.17–8.18 (m, ArH, 20H). 13C-NMR δ (p.p.m.): 55.4, 55.5(2OMe), 65.9 (C-3), 78.1 (C-4), 100.2–158.2 (aromatic carbon), 167.7 (CO β-lactam). Analysis calculated for C37H27NO4: C 80.86, H 4.95, N 2.55%. Found: C 80.03, H 4.98, N 2.83%

Refinement

The H atoms were positioned geometrically and refined in a riding model approximation with C—H = 0.93 to 0.98 Å, and with Uiso(H) = 1.2 or 1.5Ueq(C).

Figures

Fig. 1.
The molecular structure of molecule IA of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids.
Fig. 2.
The molecular structure of molecule IB of (I), with the atom-numbering scheme and 30% probability displacement ellipsoids.

Crystal data

C37H27NO4Z = 4
Mr = 549.60F(000) = 1152
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3164 (6) ÅCell parameters from 23132 reflections
b = 13.1277 (7) Åθ = 1.2–27.3°
c = 18.4838 (11) ŵ = 0.08 mm1
α = 92.434 (5)°T = 295 K
β = 109.236 (4)°Block, light-green
γ = 91.357 (4)°0.35 × 0.32 × 0.28 mm
V = 2816.9 (3) Å3

Data collection

Stoe IPDS 2 diffractometer11851 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus6076 reflections with I > 2σ(I)
plane graphiteRint = 0.100
Detector resolution: 6.67 pixels mm-1θmax = 26.8°, θmin = 1.8°
ω scansh = −15→15
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −16→16
Tmin = 0.971, Tmax = 0.977l = −23→23
30264 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.131w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3
S = 0.88(Δ/σ)max = 0.001
11851 reflectionsΔρmax = 0.18 e Å3
762 parametersΔρmin = −0.23 e Å3
2 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0068 (7)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O10.8942 (2)0.88820 (16)0.18847 (11)0.0895 (9)
O20.63763 (13)0.56579 (13)0.09096 (9)0.0674 (6)
O30.90833 (14)0.56385 (14)−0.05719 (9)0.0725 (7)
O40.69478 (19)0.27229 (16)−0.19830 (10)0.0908 (8)
N10.75037 (15)0.59802 (14)0.01293 (9)0.0524 (6)
C10.72308 (18)0.78066 (18)−0.09183 (11)0.0592 (9)
C20.6123 (2)0.7298 (2)−0.10711 (14)0.0720 (10)
C30.5219 (3)0.7432 (3)−0.17004 (16)0.0879 (13)
C40.5295 (3)0.8129 (3)−0.22451 (17)0.1029 (15)
C50.6301 (4)0.8638 (3)−0.21355 (16)0.0961 (13)
C60.7287 (3)0.8506 (2)−0.14902 (13)0.0708 (10)
C70.8339 (3)0.9000 (2)−0.14035 (15)0.0786 (13)
C80.9320 (3)0.88555 (19)−0.07957 (15)0.0690 (10)
C91.0389 (3)0.9364 (2)−0.07369 (19)0.0840 (13)
C101.1332 (3)0.9231 (2)−0.0159 (2)0.0913 (15)
C111.1318 (3)0.8585 (2)0.04329 (18)0.0878 (12)
C121.0308 (2)0.8090 (2)0.04008 (16)0.0707 (10)
C130.9280 (2)0.81834 (17)−0.02127 (13)0.0570 (8)
C140.82102 (17)0.76592 (17)−0.02899 (11)0.0541 (8)
C150.82820 (19)0.69059 (16)0.03212 (11)0.0501 (7)
C160.78066 (19)0.71268 (18)0.10240 (12)0.0545 (8)
C170.7174 (2)0.8073 (2)0.10394 (13)0.0634 (10)
C180.5995 (3)0.8159 (2)0.06731 (16)0.0796 (11)
C190.5477 (3)0.9063 (3)0.0717 (2)0.1015 (16)
C200.6127 (5)0.9907 (3)0.1132 (2)0.1125 (18)
C210.7290 (4)0.9829 (3)0.1509 (2)0.1018 (16)
C220.7789 (3)0.8925 (2)0.14681 (16)0.0741 (11)
C230.9323 (2)0.7946 (2)0.21506 (15)0.0747 (11)
C241.0304 (3)0.7936 (3)0.27988 (18)0.1009 (15)
C251.0689 (3)0.7023 (4)0.30934 (18)0.1086 (18)
C261.0104 (3)0.6127 (3)0.27628 (16)0.0884 (13)
C270.9147 (2)0.6136 (2)0.21140 (13)0.0677 (10)
C280.8755 (2)0.7047 (2)0.17832 (12)0.0599 (8)
C290.70803 (19)0.61445 (18)0.07177 (12)0.0532 (8)
C300.73190 (18)0.51789 (17)−0.04314 (11)0.0524 (7)
C310.81466 (19)0.49726 (18)−0.07871 (12)0.0548 (8)
C320.7981 (2)0.4166 (2)−0.13046 (13)0.0648 (9)
C330.7004 (2)0.3525 (2)−0.14772 (12)0.0682 (9)
C340.6163 (2)0.3748 (2)−0.11564 (13)0.0689 (9)
C350.6335 (2)0.4558 (2)−0.06368 (12)0.0637 (9)
C360.9813 (2)0.5661 (3)−0.10290 (16)0.0895 (13)
C370.5967 (3)0.2041 (3)−0.2176 (2)0.1199 (16)
O1'0.44211 (14)0.09851 (14)0.62126 (8)0.0719 (6)
O2'0.18500 (15)0.04284 (14)0.34188 (10)0.0729 (6)
O3'−0.01023 (14)0.31985 (15)0.43808 (9)0.0769 (7)
O4'−0.24931 (16)0.34781 (16)0.17933 (11)0.0885 (8)
N1'0.13169 (15)0.19227 (14)0.39409 (10)0.0520 (6)
C1'0.28673 (18)0.39075 (16)0.43460 (11)0.0508 (7)
C2'0.2675 (2)0.3577 (2)0.35600 (12)0.0635 (9)
C3'0.2940 (2)0.4195 (2)0.30641 (14)0.0765 (10)
C4'0.3409 (2)0.5182 (3)0.32963 (18)0.0871 (12)
C5'0.3623 (2)0.5540 (2)0.40215 (17)0.0777 (11)
C6'0.3372 (2)0.49171 (18)0.45703 (14)0.0600 (8)
C7'0.3643 (2)0.52860 (19)0.53249 (15)0.0689 (10)
C8'0.3451 (2)0.47047 (19)0.58850 (13)0.0599 (8)
C9'0.3769 (2)0.5086 (2)0.66671 (15)0.0788 (11)
C10'0.3577 (3)0.4526 (3)0.72053 (16)0.0867 (11)
C11'0.3086 (2)0.3547 (3)0.70069 (14)0.0799 (11)
C12'0.2770 (2)0.3136 (2)0.62795 (12)0.0648 (9)
C13'0.29286 (18)0.37098 (17)0.56685 (12)0.0512 (8)
C14'0.26145 (17)0.33231 (16)0.48937 (11)0.0471 (7)
C15'0.20202 (17)0.22763 (17)0.47349 (11)0.0487 (7)
C16'0.27389 (18)0.12751 (16)0.47554 (11)0.0494 (7)
C17'0.40112 (18)0.14129 (16)0.48928 (12)0.0494 (7)
C18'0.4458 (2)0.16801 (19)0.43213 (13)0.0627 (9)
C19'0.5634 (2)0.1823 (2)0.44889 (17)0.0704 (10)
C20'0.6365 (2)0.1699 (2)0.52095 (17)0.0746 (10)
C21'0.5956 (2)0.1404 (2)0.57790 (15)0.0713 (10)
C22'0.47776 (19)0.12735 (18)0.56074 (13)0.0560 (8)
C23'0.3361 (2)0.04727 (18)0.60154 (13)0.0579 (8)
C24'0.3182 (2)−0.0088 (2)0.65867 (15)0.0750 (10)
C25'0.2170 (3)−0.0663 (2)0.64169 (19)0.0885 (12)
C26'0.1382 (3)−0.0691 (2)0.56960 (19)0.0885 (12)
C27'0.1551 (2)−0.0086 (2)0.51410 (16)0.0751 (10)
C28'0.25504 (19)0.05271 (17)0.53059 (13)0.0550 (8)
C29'0.19331 (19)0.10879 (18)0.39218 (13)0.0541 (8)
C30'0.03498 (18)0.23067 (17)0.34005 (12)0.0511 (7)
C31'−0.0381 (2)0.29768 (18)0.36066 (13)0.0569 (8)
C32'−0.1302 (2)0.3351 (2)0.30565 (14)0.0655 (9)
C33'−0.1550 (2)0.30523 (19)0.22879 (14)0.0617 (8)
C34'−0.0870 (2)0.2385 (2)0.20754 (13)0.0656 (9)
C35'0.0076 (2)0.2021 (2)0.26307 (13)0.0627 (9)
C36'−0.0904 (3)0.3752 (4)0.46276 (19)0.1243 (18)
C37'−0.2853 (2)0.3143 (3)0.10074 (15)0.0922 (13)
H20.603000.68540−0.071500.0860*
H30.453300.70620−0.177900.1050*
H40.465800.82340−0.267300.1240*
H50.635000.90930−0.249700.1150*
H70.838000.94470−0.177200.0940*
H91.041600.97970−0.111600.1010*
H101.201700.95660−0.013900.1100*
H111.198900.849800.084000.1050*
H121.030400.768000.079800.0850*
H150.907800.669300.052900.0600*
H180.555500.759800.039600.0960*
H190.469100.911200.046900.1220*
H200.577801.052200.115500.1350*
H210.772801.038900.178800.1220*
H241.069300.854300.302800.1210*
H251.135000.700900.352000.1300*
H261.035500.551100.297800.1060*
H270.875800.552400.189500.0810*
H320.852400.40420−0.154400.0780*
H340.548400.33500−0.129400.0830*
H350.577300.46940−0.041500.0760*
H36A1.020300.50300−0.099400.1340*
H36B1.037000.62180−0.084700.1340*
H36C0.936000.57480−0.155400.1340*
H37A0.587200.18070−0.171500.1800*
H37B0.607400.14680−0.248200.1800*
H37C0.529500.23880−0.246000.1800*
H2'0.236100.292500.338600.0760*
H3'0.280700.395400.256000.0920*
H4'0.357300.559400.294500.1050*
H5'0.393700.619800.417100.0930*
H7'0.396400.594400.546100.0830*
H9'0.411400.573500.680400.0950*
H10'0.377100.479000.770800.1040*
H11'0.297000.315900.738700.0960*
H12'0.244700.247700.617100.0780*
H15'0.155600.220100.507100.0580*
H18'0.396300.176300.382600.0750*
H19'0.592500.200400.410600.0840*
H20'0.715200.181500.531800.0900*
H21'0.645800.129500.626700.0860*
H24'0.37310−0.007600.707300.0900*
H25'0.20240−0.103200.679500.1060*
H26'0.07260−0.111800.557600.1060*
H27'0.09940−0.009100.465700.0900*
H32'−0.176800.381000.319900.0790*
H34'−0.103700.217400.156200.0790*
H35'0.054300.156900.248100.0750*
H36D−0.093700.443200.445100.1870*
H36E−0.066600.378200.517800.1870*
H36F−0.165100.341700.442100.1870*
H37D−0.226200.331600.079600.1380*
H37E−0.354700.347000.073400.1380*
H37F−0.299300.241700.096100.1380*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.1113 (18)0.0758 (14)0.0818 (13)−0.0323 (12)0.0361 (13)−0.0047 (11)
O20.0648 (10)0.0836 (12)0.0618 (9)−0.0163 (9)0.0331 (9)0.0036 (8)
O30.0656 (11)0.0824 (12)0.0809 (11)−0.0140 (9)0.0425 (10)−0.0095 (9)
O40.1228 (17)0.0850 (14)0.0636 (11)−0.0187 (12)0.0334 (12)−0.0161 (10)
N10.0546 (11)0.0603 (12)0.0465 (10)−0.0093 (9)0.0238 (9)−0.0006 (9)
C10.0729 (17)0.0651 (15)0.0457 (12)0.0114 (12)0.0269 (13)0.0056 (11)
C20.0638 (17)0.097 (2)0.0543 (14)0.0118 (14)0.0179 (14)0.0041 (14)
C30.080 (2)0.112 (3)0.0657 (17)0.0220 (17)0.0150 (16)0.0024 (17)
C40.107 (3)0.129 (3)0.0591 (18)0.040 (2)0.0062 (18)0.0093 (19)
C50.143 (3)0.093 (2)0.0521 (16)0.031 (2)0.029 (2)0.0157 (15)
C60.105 (2)0.0663 (16)0.0495 (14)0.0217 (15)0.0348 (15)0.0095 (12)
C70.133 (3)0.0616 (16)0.0611 (16)0.0122 (16)0.0572 (19)0.0134 (13)
C80.105 (2)0.0530 (14)0.0681 (16)0.0006 (14)0.0545 (17)0.0056 (12)
C90.120 (3)0.0626 (17)0.095 (2)−0.0163 (18)0.072 (2)−0.0002 (16)
C100.108 (3)0.0705 (19)0.120 (3)−0.0249 (19)0.075 (2)−0.0120 (19)
C110.080 (2)0.080 (2)0.110 (2)−0.0186 (16)0.0430 (18)−0.0053 (17)
C120.0687 (17)0.0655 (17)0.0817 (17)−0.0126 (13)0.0309 (16)0.0069 (14)
C130.0719 (16)0.0488 (13)0.0608 (14)−0.0006 (11)0.0365 (14)0.0026 (11)
C140.0657 (15)0.0553 (14)0.0488 (12)−0.0004 (11)0.0291 (12)0.0045 (10)
C150.0532 (13)0.0542 (13)0.0465 (11)−0.0024 (10)0.0212 (10)0.0058 (10)
C160.0626 (14)0.0605 (14)0.0463 (12)−0.0084 (11)0.0267 (11)0.0038 (10)
C170.0811 (19)0.0679 (17)0.0537 (13)−0.0001 (14)0.0385 (14)0.0096 (12)
C180.095 (2)0.085 (2)0.0729 (17)0.0188 (16)0.0444 (17)0.0165 (15)
C190.120 (3)0.109 (3)0.096 (2)0.038 (2)0.058 (2)0.032 (2)
C200.189 (4)0.078 (2)0.113 (3)0.037 (3)0.103 (3)0.022 (2)
C210.164 (4)0.072 (2)0.098 (2)0.001 (2)0.082 (3)0.0077 (18)
C220.108 (2)0.0608 (18)0.0696 (17)−0.0034 (17)0.0513 (18)0.0068 (14)
C230.083 (2)0.086 (2)0.0575 (15)−0.0246 (16)0.0288 (15)−0.0010 (14)
C240.098 (3)0.124 (3)0.0698 (19)−0.042 (2)0.0188 (19)−0.016 (2)
C250.093 (3)0.153 (4)0.0645 (19)−0.016 (3)0.0070 (18)0.003 (2)
C260.084 (2)0.117 (3)0.0599 (16)0.0094 (19)0.0168 (16)0.0128 (17)
C270.0695 (17)0.0849 (19)0.0496 (13)−0.0026 (14)0.0209 (13)0.0054 (13)
C280.0607 (14)0.0778 (17)0.0451 (12)−0.0137 (13)0.0241 (12)0.0013 (12)
C290.0546 (13)0.0630 (14)0.0466 (12)0.0001 (11)0.0223 (11)0.0086 (10)
C300.0540 (13)0.0620 (14)0.0415 (11)−0.0062 (11)0.0167 (11)0.0043 (10)
C310.0575 (14)0.0598 (14)0.0479 (12)−0.0020 (11)0.0184 (11)0.0077 (11)
C320.0744 (17)0.0748 (17)0.0505 (13)−0.0006 (14)0.0278 (13)0.0047 (12)
C330.0894 (19)0.0705 (17)0.0401 (12)−0.0072 (14)0.0166 (13)−0.0009 (12)
C340.0692 (16)0.0825 (19)0.0500 (13)−0.0185 (14)0.0153 (13)−0.0036 (13)
C350.0582 (15)0.0841 (18)0.0488 (13)−0.0129 (13)0.0194 (12)0.0000 (12)
C360.0777 (19)0.119 (3)0.0907 (19)−0.0113 (17)0.0545 (17)0.0046 (18)
C370.129 (3)0.109 (3)0.099 (2)−0.031 (2)0.016 (2)−0.047 (2)
O1'0.0662 (11)0.0938 (13)0.0491 (9)−0.0157 (9)0.0113 (8)0.0045 (9)
O2'0.0773 (12)0.0655 (11)0.0663 (10)0.0034 (9)0.0125 (9)−0.0114 (9)
O3'0.0658 (11)0.1052 (15)0.0563 (10)0.0190 (10)0.0164 (9)−0.0092 (9)
O4'0.0755 (13)0.0963 (15)0.0741 (12)0.0140 (11)−0.0030 (10)0.0089 (11)
N1'0.0498 (11)0.0558 (12)0.0479 (10)0.0009 (9)0.0129 (9)0.0013 (8)
C1'0.0481 (12)0.0543 (13)0.0516 (12)0.0068 (10)0.0174 (10)0.0113 (10)
C2'0.0618 (15)0.0791 (18)0.0511 (13)−0.0042 (13)0.0204 (12)0.0110 (12)
C3'0.0785 (18)0.095 (2)0.0589 (15)0.0021 (16)0.0243 (14)0.0257 (14)
C4'0.081 (2)0.102 (2)0.083 (2)−0.0029 (17)0.0292 (17)0.0449 (18)
C5'0.0785 (19)0.0649 (17)0.092 (2)−0.0020 (14)0.0286 (16)0.0282 (15)
C6'0.0566 (14)0.0554 (14)0.0704 (15)0.0062 (11)0.0226 (12)0.0142 (12)
C7'0.0702 (17)0.0518 (15)0.0819 (18)−0.0039 (12)0.0226 (14)−0.0032 (13)
C8'0.0584 (15)0.0594 (15)0.0612 (14)0.0089 (11)0.0198 (12)−0.0069 (12)
C9'0.0797 (19)0.0786 (19)0.0730 (17)0.0034 (15)0.0218 (15)−0.0240 (15)
C10'0.099 (2)0.105 (2)0.0563 (15)0.0159 (18)0.0278 (16)−0.0171 (16)
C11'0.094 (2)0.101 (2)0.0542 (15)0.0133 (17)0.0372 (15)0.0015 (15)
C12'0.0734 (17)0.0765 (17)0.0502 (13)0.0039 (13)0.0281 (13)0.0024 (12)
C13'0.0494 (13)0.0556 (14)0.0516 (12)0.0088 (10)0.0205 (11)0.0004 (10)
C14'0.0472 (12)0.0501 (12)0.0467 (11)0.0056 (9)0.0187 (10)0.0041 (9)
C15'0.0473 (12)0.0575 (13)0.0411 (11)−0.0020 (10)0.0144 (10)0.0040 (10)
C16'0.0496 (13)0.0483 (12)0.0487 (12)0.0013 (10)0.0138 (10)0.0061 (10)
C17'0.0506 (13)0.0443 (12)0.0530 (13)0.0010 (10)0.0171 (11)0.0004 (10)
C18'0.0663 (16)0.0672 (16)0.0590 (14)−0.0010 (12)0.0270 (13)0.0026 (12)
C19'0.0698 (17)0.0685 (17)0.0844 (19)−0.0041 (13)0.0427 (16)−0.0060 (14)
C20'0.0550 (16)0.0741 (18)0.097 (2)−0.0088 (13)0.0308 (16)−0.0112 (15)
C21'0.0563 (16)0.0792 (19)0.0709 (16)−0.0036 (13)0.0122 (13)−0.0038 (14)
C22'0.0526 (14)0.0565 (14)0.0561 (13)−0.0041 (11)0.0151 (12)0.0003 (11)
C23'0.0559 (14)0.0592 (14)0.0581 (14)−0.0017 (11)0.0176 (12)0.0101 (11)
C24'0.0860 (19)0.0779 (18)0.0648 (15)0.0094 (15)0.0270 (15)0.0241 (13)
C25'0.091 (2)0.090 (2)0.096 (2)0.0003 (17)0.043 (2)0.0369 (18)
C26'0.074 (2)0.086 (2)0.111 (2)−0.0126 (16)0.0361 (19)0.0298 (18)
C27'0.0599 (16)0.0746 (18)0.0873 (18)−0.0075 (13)0.0183 (14)0.0225 (15)
C28'0.0501 (13)0.0529 (13)0.0622 (14)0.0029 (10)0.0179 (12)0.0110 (11)
C29'0.0556 (14)0.0513 (14)0.0535 (13)−0.0021 (11)0.0160 (11)0.0006 (11)
C30'0.0459 (12)0.0553 (13)0.0505 (12)−0.0011 (10)0.0133 (11)0.0075 (10)
C31'0.0546 (14)0.0588 (14)0.0554 (14)−0.0020 (11)0.0160 (12)0.0021 (11)
C32'0.0570 (15)0.0667 (16)0.0686 (16)0.0081 (12)0.0150 (13)0.0013 (13)
C33'0.0518 (14)0.0608 (15)0.0635 (15)−0.0007 (12)0.0063 (12)0.0105 (12)
C34'0.0647 (16)0.0765 (18)0.0497 (13)−0.0015 (14)0.0109 (13)0.0048 (12)
C35'0.0631 (15)0.0724 (17)0.0511 (13)0.0076 (12)0.0167 (12)0.0010 (12)
C36'0.106 (3)0.180 (4)0.086 (2)0.056 (2)0.031 (2)−0.025 (2)
C37'0.0740 (19)0.125 (3)0.0639 (17)−0.0091 (18)0.0028 (15)0.0243 (17)

Geometric parameters (Å, °)

O1—C221.378 (4)C27—H270.9300
O1—C231.378 (3)C32—H320.9300
O2—C291.217 (3)C34—H340.9300
O3—C311.369 (3)C35—H350.9300
O3—C361.423 (3)C36—H36C0.9600
O4—C331.363 (3)C36—H36B0.9600
O4—C371.423 (5)C36—H36A0.9600
O1'—C23'1.384 (3)C37—H37A0.9600
O1'—C22'1.393 (3)C37—H37B0.9600
O2'—C29'1.220 (3)C37—H37C0.9600
O3'—C31'1.374 (3)C1'—C2'1.439 (3)
O3'—C36'1.419 (5)C1'—C6'1.435 (3)
O4'—C33'1.368 (3)C1'—C14'1.405 (3)
O4'—C37'1.419 (3)C2'—C3'1.361 (4)
N1—C151.485 (3)C3'—C4'1.397 (5)
N1—C291.364 (3)C4'—C5'1.340 (4)
N1—C301.405 (3)C5'—C6'1.435 (4)
N1'—C15'1.485 (3)C6'—C7'1.386 (4)
N1'—C29'1.354 (3)C7'—C8'1.389 (4)
N1'—C30'1.399 (3)C8'—C9'1.432 (3)
C1—C21.440 (3)C8'—C13'1.423 (3)
C1—C61.447 (3)C9'—C10'1.340 (4)
C1—C141.396 (3)C10'—C11'1.389 (5)
C2—C31.341 (4)C11'—C12'1.354 (3)
C3—C41.413 (5)C12'—C13'1.446 (3)
C4—C51.344 (6)C13'—C14'1.422 (3)
C5—C61.414 (5)C14'—C15'1.512 (3)
C6—C71.393 (5)C15'—C16'1.597 (3)
C7—C81.376 (4)C16'—C17'1.508 (3)
C8—C91.431 (5)C16'—C28'1.511 (3)
C8—C131.434 (4)C16'—C29'1.539 (3)
C9—C101.315 (5)C17'—C18'1.395 (3)
C10—C111.417 (4)C17'—C22'1.370 (3)
C11—C121.372 (4)C18'—C19'1.384 (4)
C12—C131.406 (4)C19'—C20'1.359 (4)
C13—C141.434 (3)C20'—C21'1.374 (4)
C14—C151.515 (3)C21'—C22'1.384 (4)
C15—C161.610 (3)C23'—C24'1.385 (4)
C16—C171.486 (4)C23'—C28'1.368 (3)
C16—C281.511 (3)C24'—C25'1.378 (4)
C16—C291.528 (3)C25'—C26'1.364 (5)
C17—C221.394 (4)C26'—C27'1.389 (4)
C17—C181.395 (4)C27'—C28'1.393 (4)
C18—C191.373 (5)C30'—C31'1.402 (3)
C19—C201.392 (6)C30'—C35'1.383 (3)
C20—C211.380 (7)C31'—C32'1.368 (3)
C21—C221.360 (5)C32'—C33'1.388 (3)
C23—C281.387 (4)C33'—C34'1.359 (4)
C23—C241.394 (4)C34'—C35'1.385 (3)
C24—C251.368 (6)C2'—H2'0.9300
C25—C261.373 (6)C3'—H3'0.9300
C26—C271.378 (4)C4'—H4'0.9300
C27—C281.390 (4)C5'—H5'0.9300
C30—C311.409 (3)C7'—H7'0.9300
C30—C351.379 (3)C9'—H9'0.9300
C31—C321.361 (3)C10'—H10'0.9300
C32—C331.391 (4)C11'—H11'0.9300
C33—C341.384 (4)C12'—H12'0.9300
C34—C351.366 (3)C15'—H15'0.9800
C2—H20.9300C18'—H18'0.9300
C3—H30.9300C19'—H19'0.9300
C4—H40.9300C20'—H20'0.9300
C5—H50.9300C21'—H21'0.9300
C7—H70.9300C24'—H24'0.9300
C9—H90.9300C25'—H25'0.9300
C10—H100.9300C26'—H26'0.9300
C11—H110.9300C27'—H27'0.9300
C12—H120.9300C32'—H32'0.9300
C15—H150.9800C34'—H34'0.9300
C18—H180.9300C35'—H35'0.9300
C19—H190.9300C36'—H36D0.9600
C20—H200.9300C36'—H36E0.9600
C21—H210.9300C36'—H36F0.9600
C24—H240.9300C37'—H37D0.9600
C25—H250.9300C37'—H37E0.9600
C26—H260.9300C37'—H37F0.9600
O1'···C37i3.195 (4)C30···H22.7100
O2···C183.354 (3)C30'···H2'2.6000
O2···C353.132 (3)C30'···H26'viii3.0900
O2···C34ii3.409 (3)C31'···H26'viii3.0200
O2···C35ii3.212 (3)C32···H36C2.8000
O2'···C35'3.106 (3)C32···H36A2.8100
O2'···C27'3.416 (3)C32···H4'ii3.0400
O3···N12.705 (3)C32'···H36F2.6900
O3···C133.366 (3)C32'···H36D2.7800
O3···O3iii3.117 (2)C33···H11iii3.0700
O3···C36iii3.377 (4)C33···H4'ii2.8700
O3···C152.718 (3)C34···H37C2.8300
O3···C142.975 (3)C34···H37A2.6800
O3'···C14'3.161 (3)C34'···H37F2.7500
O3'···C15'2.796 (3)C34'···H21vii3.0300
O3'···N1'2.735 (3)C34'···H37D2.7700
O1···H9iv2.5600C35···H37Evi2.9300
O1'···H37Bi2.6300C35···H23.0500
O1'···H37Ci2.8900C35'···H2'2.9000
O2···H10'v2.7100C36···H322.5700
O2···H37Evi2.8800C36'···H32'2.5100
O2···H182.8500C37···H342.5300
O2···H272.9100C37···H11iii3.0100
O2···H35ii2.5200C37'···H34'2.5300
O2···H352.5800C37'···H3ix2.8900
O2'···H27'2.9200H2···C183.0400
O2'···H24vii2.7700H2···N12.3300
O2'···H35'2.5200H2···C152.8000
O3···H36Aiii2.9100H2···C292.7500
O3···H152.4100H2···C302.7100
O3'···H26'viii2.8300H2···C353.0500
O3'···H15'2.4600H2···H182.4800
O4···H4'ii2.8500H2'···C35'2.9000
O4···H11iii2.7000H2'···H18'2.4600
O4'···H3ix2.5900H2'···C15'2.8200
N1···C22.964 (3)H2'···C29'2.7500
N1···O32.705 (3)H2'···N1'2.3100
N1'···C2'2.957 (3)H2'···C30'2.6000
N1'···O3'2.735 (3)H3···C37'ix2.8900
N1···H22.3300H3···O4'ix2.5900
N1'···H2'2.3100H4···H24'xv2.5100
C1···C303.597 (3)H4···C24'xv2.9700
C1'···C18'3.565 (3)H4···H19'ii2.5100
C1'···C30'3.591 (3)H4'···O4ii2.8500
C2···C303.261 (3)H4'···C33ii2.8700
C2···C293.544 (3)H4'···C32ii3.0400
C2···N12.964 (3)H5···H18'ii2.5600
C2···C183.425 (4)H5···H72.4400
C2'···C18'3.395 (4)H5'···C20'v3.0200
C2'···C29'3.522 (4)H5'···H7'2.4100
C2'···C30'3.201 (3)H7···H92.4200
C2'···N1'2.957 (3)H7···H35'ii2.5200
C4'···C9'v3.481 (4)H7···H52.4400
C5'···C7'v3.403 (4)H7'···C19'v2.9500
C5'···C8'v3.573 (4)H7'···H5'2.4100
C7···C11iv3.522 (4)H7'···H9'2.4600
C7···C10iv3.537 (4)H9···H72.4200
C7'···C5'v3.403 (4)H9···O1iv2.5600
C8···C10iv3.274 (4)H9···C22iv3.0000
C8···C11iv3.555 (4)H9'···H7'2.4600
C8···C9iv3.514 (4)H10···C21iv3.0600
C8'···C5'v3.573 (4)H10'···O2v2.7100
C9···C34'ii3.506 (4)H11···C33iii3.0700
C9···C10iv3.588 (5)H11···C37iii3.0100
C9···C13iv3.550 (4)H11···O4iii2.7000
C9···C11iv3.592 (5)H11'···C28v3.0200
C9···C9iv3.541 (5)H12···C152.5200
C9···C8iv3.514 (4)H12···H151.8900
C9···C12iv3.550 (4)H12'···C15'2.5300
C9'···C4'v3.481 (4)H12'···H15'1.9800
C10···C8iv3.274 (4)H12'···C23'2.9300
C10···C7iv3.537 (4)H12'···C28'2.9900
C10···C13iv3.581 (4)H15···O32.4100
C10···C9iv3.588 (5)H15···H121.8900
C11···C9iv3.592 (5)H15···C122.4200
C11···C7iv3.522 (4)H15···C273.0200
C11···C8iv3.555 (4)H15···H36Aiii2.5300
C12···C9iv3.550 (4)H15'···O3'2.4600
C13···C10iv3.581 (4)H15'···C12'2.4900
C13···C9iv3.550 (4)H15'···C27'3.0100
C13···O33.366 (3)H15'···H12'1.9800
C14···O32.975 (3)H18···O22.8500
C14···C313.599 (3)H18···C23.0300
C14'···O3'3.161 (3)H18···C292.6600
C14'···C18'3.542 (3)H18···H22.4800
C15···O32.718 (3)H18'···C29'2.7000
C15'···O3'2.796 (3)H18'···H2'2.4600
C18···O23.354 (3)H18'···C2'2.8600
C18···C23.425 (4)H18'···H5ii2.5600
C18'···C1'3.565 (3)H18'···C5ii3.0500
C18'···C14'3.542 (3)H19'···H4ii2.5100
C18'···C2'3.395 (4)H20'···C27'x3.0500
C19'···C24'x3.599 (4)H21···C34'xvi3.0300
C19'···C23'x3.490 (4)H21'···H37Bi2.5100
C20'···C27'x3.568 (4)H24···O2'xvi2.7700
C20'···C28'x3.467 (4)H24'···H4xiv2.5100
C23'···C19'x3.490 (4)H26'···C30'viii3.0900
C24'···C19'x3.599 (4)H26'···O3'viii2.8300
C27···C36iii3.558 (4)H26'···C31'viii3.0200
C27'···C20'x3.568 (4)H27···H36Aiii2.5100
C27'···O2'3.416 (3)H27···O22.9100
C28'···C20'x3.467 (4)H27···C292.6300
C29···C23.544 (3)H27'···C29'2.5900
C29'···C2'3.522 (4)H27'···O2'2.9200
C30···C23.261 (3)H27'···C26'viii3.0000
C30···C13.597 (3)H32···C362.5700
C30'···C2'3.201 (3)H32···H36C2.4500
C30'···C1'3.591 (3)H32···H36A2.3200
C31···C143.599 (3)H32'···H36D2.3000
C34···O2ii3.409 (3)H32'···H36F2.3000
C34'···C9ii3.506 (4)H32'···C10'xiii3.0900
C35···O2ii3.212 (3)H32'···C9'xiii2.9600
C35···C37'vi3.500 (4)H32'···C36'2.5100
C35···O23.132 (3)H34···C372.5300
C35'···O2'3.106 (3)H34···H37A2.2600
C36···O3iii3.377 (4)H34···H37C2.3900
C36···C27iii3.558 (4)H34'···C37'2.5300
C37···O1'xi3.195 (4)H34'···H37F2.3300
C37'···C35xii3.500 (4)H34'···C9ii2.7700
C2···H183.0300H34'···C10ii3.0300
C2'···H18'2.8600H34'···H37D2.3300
C5···H18'ii3.0500H35···O22.5800
C7···H35'ii2.8500H35···C292.8100
C9···H34'ii2.7700H35···O2ii2.5200
C9'···H32'xiii2.9600H35'···C29'2.7600
C10···H34'ii3.0300H35'···C7ii2.8500
C10'···H32'xiii3.0900H35'···O2'2.5200
C11'···H37Ci3.0400H35'···H7ii2.5200
C12···H152.4200H36A···H322.3200
C12'···H15'2.4900H36A···O3iii2.9100
C15···H22.8000H36A···C322.8100
C15···H122.5200H36A···C27iii2.8500
C15'···H12'2.5300H36A···H15iii2.5300
C15'···H2'2.8200H36A···H27iii2.5100
C18···H23.0400H36B···H37Dii2.3700
C19···H37Aii3.0900H36C···C322.8000
C19'···H7'v2.9500H36C···H322.4500
C20'···H5'v3.0200H36D···C32'2.7800
C21···H10iv3.0600H36D···H32'2.3000
C22···H9iv3.0000H36F···C32'2.6900
C23'···H12'2.9300H36F···H32'2.3000
C24'···H4xiv2.9700H37A···C342.6800
C26'···H27'viii3.0000H37A···H342.2600
C27···H36Aiii2.8500H37A···C19ii3.0900
C27···H153.0200H37B···O1'xi2.6300
C27'···H20'x3.0500H37B···H21'xi2.5100
C27'···H15'3.0100H37C···C342.8300
C28···H11'v3.0200H37C···H342.3900
C28'···H12'2.9900H37C···C11'xi3.0400
C29···H352.8100H37C···O1'xi2.8900
C29···H182.6600H37D···C34'2.7700
C29···H272.6300H37D···H34'2.3300
C29···H22.7500H37D···H36Bii2.3700
C29'···H27'2.5900H37E···O2xii2.8800
C29'···H18'2.7000H37E···C35xii2.9300
C29'···H35'2.7600H37F···C34'2.7500
C29'···H2'2.7500H37F···H34'2.3300
C22—O1—C23116.5 (2)H37B—C37—H37C110.00
C31—O3—C36118.9 (2)O4—C37—H37A109.00
C33—O4—C37117.5 (2)O4—C37—H37B109.00
C22'—O1'—C23'116.38 (17)O4—C37—H37C109.00
C31'—O3'—C36'117.2 (2)H37A—C37—H37B109.00
C33'—O4'—C37'118.3 (2)H37A—C37—H37C109.00
C15—N1—C30132.54 (18)C2'—C1'—C6'115.6 (2)
C15—N1—C2995.21 (16)C2'—C1'—C14'125.4 (2)
C29—N1—C30132.2 (2)C6'—C1'—C14'119.02 (19)
C15'—N1'—C29'95.05 (17)C1'—C2'—C3'121.7 (2)
C15'—N1'—C30'132.80 (18)C2'—C3'—C4'121.4 (2)
C29'—N1'—C30'132.15 (19)C3'—C4'—C5'120.4 (3)
C2—C1—C14125.5 (2)C4'—C5'—C6'120.6 (3)
C2—C1—C6114.6 (2)C1'—C6'—C5'120.4 (2)
C6—C1—C14120.0 (2)C1'—C6'—C7'119.9 (2)
C1—C2—C3123.3 (3)C5'—C6'—C7'119.7 (2)
C2—C3—C4120.8 (3)C6'—C7'—C8'122.1 (2)
C3—C4—C5119.0 (3)C7'—C8'—C9'121.4 (2)
C4—C5—C6122.3 (3)C7'—C8'—C13'118.7 (2)
C5—C6—C7121.7 (3)C9'—C8'—C13'120.0 (2)
C1—C6—C5119.9 (3)C8'—C9'—C10'121.3 (3)
C1—C6—C7118.4 (2)C9'—C10'—C11'119.6 (3)
C6—C7—C8122.8 (3)C10'—C11'—C12'122.3 (3)
C9—C8—C13119.2 (3)C11'—C12'—C13'120.9 (3)
C7—C8—C9120.9 (3)C8'—C13'—C12'116.0 (2)
C7—C8—C13119.9 (3)C8'—C13'—C14'120.4 (2)
C8—C9—C10121.4 (3)C12'—C13'—C14'123.6 (2)
C9—C10—C11120.8 (3)C1'—C14'—C13'119.83 (19)
C10—C11—C12119.5 (3)C1'—C14'—C15'125.23 (18)
C11—C12—C13122.1 (3)C13'—C14'—C15'114.95 (18)
C12—C13—C14124.6 (2)N1'—C15'—C14'120.43 (17)
C8—C13—C14118.5 (2)N1'—C15'—C16'86.90 (15)
C8—C13—C12116.9 (2)C14'—C15'—C16'120.73 (18)
C1—C14—C13120.5 (2)C15'—C16'—C17'117.84 (18)
C1—C14—C15125.0 (2)C15'—C16'—C28'111.94 (18)
C13—C14—C15114.34 (18)C15'—C16'—C29'83.84 (15)
N1—C15—C14119.47 (17)C17'—C16'—C28'109.19 (18)
N1—C15—C1686.38 (16)C17'—C16'—C29'117.87 (18)
C14—C15—C16123.19 (18)C28'—C16'—C29'114.37 (19)
C15—C16—C28110.67 (19)C16'—C17'—C18'123.00 (19)
C15—C16—C17118.62 (18)C16'—C17'—C22'119.4 (2)
C15—C16—C2984.27 (16)C18'—C17'—C22'117.6 (2)
C17—C16—C28109.82 (19)C17'—C18'—C19'120.3 (2)
C17—C16—C29116.8 (2)C18'—C19'—C20'120.4 (3)
C28—C16—C29114.7 (2)C19'—C20'—C21'120.8 (3)
C16—C17—C22118.0 (2)C20'—C21'—C22'118.3 (2)
C18—C17—C22117.5 (3)O1'—C22'—C17'122.0 (2)
C16—C17—C18124.4 (2)O1'—C22'—C21'115.3 (2)
C17—C18—C19120.7 (3)C17'—C22'—C21'122.6 (2)
C18—C19—C20120.1 (4)O1'—C23'—C24'115.3 (2)
C19—C20—C21119.9 (4)O1'—C23'—C28'121.9 (2)
C20—C21—C22119.4 (4)C24'—C23'—C28'122.8 (2)
O1—C22—C17121.0 (3)C23'—C24'—C25'118.4 (3)
O1—C22—C21116.6 (3)C24'—C25'—C26'120.2 (3)
C17—C22—C21122.4 (3)C25'—C26'—C27'120.5 (3)
O1—C23—C28121.2 (2)C26'—C27'—C28'120.3 (3)
O1—C23—C24117.6 (3)C16'—C28'—C23'119.5 (2)
C24—C23—C28121.3 (3)C16'—C28'—C27'122.9 (2)
C23—C24—C25119.3 (3)C23'—C28'—C27'117.5 (2)
C24—C25—C26120.4 (3)O2'—C29'—N1'131.9 (2)
C25—C26—C27120.3 (3)O2'—C29'—C16'134.0 (2)
C26—C27—C28120.9 (3)N1'—C29'—C16'94.11 (17)
C23—C28—C27117.7 (2)N1'—C30'—C31'122.48 (19)
C16—C28—C27124.8 (2)N1'—C30'—C35'120.2 (2)
C16—C28—C23117.4 (2)C31'—C30'—C35'117.3 (2)
N1—C29—C1694.15 (18)O3'—C31'—C30'115.0 (2)
O2—C29—N1131.3 (2)O3'—C31'—C32'124.5 (2)
O2—C29—C16134.6 (2)C30'—C31'—C32'120.4 (2)
C31—C30—C35118.1 (2)C31'—C32'—C33'120.8 (2)
N1—C30—C31120.9 (2)O4'—C33'—C32'115.3 (2)
N1—C30—C35121.0 (2)O4'—C33'—C34'124.8 (2)
O3—C31—C30114.82 (19)C32'—C33'—C34'119.9 (2)
O3—C31—C32124.8 (2)C33'—C34'—C35'119.4 (2)
C30—C31—C32120.3 (2)C30'—C35'—C34'122.2 (2)
C31—C32—C33120.4 (2)C1'—C2'—H2'119.00
C32—C33—C34119.6 (2)C3'—C2'—H2'119.00
O4—C33—C34125.1 (2)C2'—C3'—H3'119.00
O4—C33—C32115.3 (2)C4'—C3'—H3'119.00
C33—C34—C35119.6 (2)C3'—C4'—H4'120.00
C30—C35—C34121.8 (2)C5'—C4'—H4'120.00
C3—C2—H2118.00C4'—C5'—H5'120.00
C1—C2—H2118.00C6'—C5'—H5'120.00
C2—C3—H3120.00C6'—C7'—H7'119.00
C4—C3—H3120.00C8'—C7'—H7'119.00
C3—C4—H4120.00C8'—C9'—H9'119.00
C5—C4—H4121.00C10'—C9'—H9'119.00
C6—C5—H5119.00C9'—C10'—H10'120.00
C4—C5—H5119.00C11'—C10'—H10'120.00
C6—C7—H7119.00C10'—C11'—H11'119.00
C8—C7—H7119.00C12'—C11'—H11'119.00
C8—C9—H9119.00C11'—C12'—H12'120.00
C10—C9—H9119.00C13'—C12'—H12'120.00
C11—C10—H10120.00N1'—C15'—H15'109.00
C9—C10—H10120.00C14'—C15'—H15'109.00
C10—C11—H11120.00C16'—C15'—H15'109.00
C12—C11—H11120.00C17'—C18'—H18'120.00
C11—C12—H12119.00C19'—C18'—H18'120.00
C13—C12—H12119.00C18'—C19'—H19'120.00
C14—C15—H15109.00C20'—C19'—H19'120.00
N1—C15—H15109.00C19'—C20'—H20'120.00
C16—C15—H15109.00C21'—C20'—H20'120.00
C19—C18—H18120.00C20'—C21'—H21'121.00
C17—C18—H18120.00C22'—C21'—H21'121.00
C18—C19—H19120.00C23'—C24'—H24'121.00
C20—C19—H19120.00C25'—C24'—H24'121.00
C19—C20—H20120.00C24'—C25'—H25'120.00
C21—C20—H20120.00C26'—C25'—H25'120.00
C22—C21—H21120.00C25'—C26'—H26'120.00
C20—C21—H21120.00C27'—C26'—H26'120.00
C23—C24—H24120.00C26'—C27'—H27'120.00
C25—C24—H24120.00C28'—C27'—H27'120.00
C26—C25—H25120.00C31'—C32'—H32'120.00
C24—C25—H25120.00C33'—C32'—H32'120.00
C25—C26—H26120.00C33'—C34'—H34'120.00
C27—C26—H26120.00C35'—C34'—H34'120.00
C26—C27—H27120.00C30'—C35'—H35'119.00
C28—C27—H27120.00C34'—C35'—H35'119.00
C33—C32—H32120.00O3'—C36'—H36D109.00
C31—C32—H32120.00O3'—C36'—H36E109.00
C33—C34—H34120.00O3'—C36'—H36F110.00
C35—C34—H34120.00H36D—C36'—H36E109.00
C30—C35—H35119.00H36D—C36'—H36F109.00
C34—C35—H35119.00H36E—C36'—H36F109.00
H36A—C36—H36B109.00O4'—C37'—H37D109.00
H36A—C36—H36C109.00O4'—C37'—H37E109.00
O3—C36—H36A109.00O4'—C37'—H37F109.00
O3—C36—H36B109.00H37D—C37'—H37E109.00
O3—C36—H36C110.00H37D—C37'—H37F110.00
H36B—C36—H36C110.00H37E—C37'—H37F110.00
C23—O1—C22—C21150.1 (3)C24—C23—C28—C16−171.4 (3)
C22—O1—C23—C24−154.9 (3)C28—C23—C24—C25−2.4 (5)
C22—O1—C23—C2825.5 (4)C23—C24—C25—C26−1.2 (5)
C23—O1—C22—C17−29.0 (4)C24—C25—C26—C272.4 (5)
C36—O3—C31—C3215.5 (4)C25—C26—C27—C28−0.1 (5)
C36—O3—C31—C30−164.2 (2)C26—C27—C28—C16172.3 (3)
C37—O4—C33—C32179.7 (2)C26—C27—C28—C23−3.3 (4)
C37—O4—C33—C34−2.3 (4)C35—C30—C31—C32−1.5 (3)
C22'—O1'—C23'—C28'−20.5 (3)N1—C30—C31—O3−3.3 (3)
C23'—O1'—C22'—C21'−155.5 (2)N1—C30—C31—C32177.1 (2)
C22'—O1'—C23'—C24'159.9 (2)C31—C30—C35—C341.5 (3)
C23'—O1'—C22'—C17'24.3 (3)C35—C30—C31—O3178.1 (2)
C36'—O3'—C31'—C32'8.0 (4)N1—C30—C35—C34−177.1 (2)
C36'—O3'—C31'—C30'−171.1 (3)O3—C31—C32—C33179.2 (2)
C37'—O4'—C33'—C34'5.4 (4)C30—C31—C32—C33−1.2 (4)
C37'—O4'—C33'—C32'−174.9 (2)C31—C32—C33—C344.1 (4)
C15—N1—C29—C16−0.12 (18)C31—C32—C33—O4−177.8 (2)
C30—N1—C15—C16−176.3 (2)O4—C33—C34—C35178.0 (2)
C29—N1—C15—C160.11 (17)C32—C33—C34—C35−4.1 (4)
C30—N1—C29—C16176.4 (2)C33—C34—C35—C301.4 (4)
C15—N1—C30—C35−161.6 (2)C6'—C1'—C14'—C15'176.2 (2)
C29—N1—C30—C3523.2 (4)C14'—C1'—C6'—C7'2.5 (4)
C29—N1—C30—C31−155.4 (2)C2'—C1'—C14'—C13'175.1 (2)
C29—N1—C15—C14−126.4 (2)C14'—C1'—C6'—C5'−179.0 (2)
C30—N1—C29—O2−3.5 (4)C6'—C1'—C14'—C13'−4.1 (3)
C30—N1—C15—C1457.2 (3)C14'—C1'—C2'—C3'179.7 (2)
C15—N1—C29—O2−179.9 (3)C2'—C1'—C6'—C5'1.7 (3)
C15—N1—C30—C3119.9 (3)C2'—C1'—C6'—C7'−176.8 (2)
C29'—N1'—C15'—C14'121.7 (2)C6'—C1'—C2'—C3'−1.1 (4)
C29'—N1'—C30'—C35'−21.0 (4)C2'—C1'—C14'—C15'−4.6 (4)
C29'—N1'—C30'—C31'158.4 (2)C1'—C2'—C3'—C4'−0.2 (4)
C29'—N1'—C15'—C16'−2.44 (17)C2'—C3'—C4'—C5'0.8 (4)
C30'—N1'—C15'—C16'177.1 (2)C3'—C4'—C5'—C6'−0.1 (4)
C15'—N1'—C30'—C35'159.7 (2)C4'—C5'—C6'—C1'−1.2 (4)
C30'—N1'—C29'—C16'−177.0 (2)C4'—C5'—C6'—C7'177.4 (3)
C30'—N1'—C29'—O2'2.2 (5)C5'—C6'—C7'—C8'−178.0 (2)
C30'—N1'—C15'—C14'−58.8 (3)C1'—C6'—C7'—C8'0.5 (4)
C15'—N1'—C29'—O2'−178.3 (3)C6'—C7'—C8'—C9'178.0 (2)
C15'—N1'—C30'—C31'−20.9 (4)C6'—C7'—C8'—C13'−1.8 (4)
C15'—N1'—C29'—C16'2.54 (18)C7'—C8'—C13'—C14'0.2 (4)
C2—C1—C6—C7−177.5 (2)C9'—C8'—C13'—C12'−0.9 (3)
C6—C1—C14—C15−176.3 (2)C7'—C8'—C9'—C10'179.6 (3)
C14—C1—C6—C71.5 (4)C7'—C8'—C13'—C12'179.0 (2)
C2—C1—C6—C5−0.3 (4)C13'—C8'—C9'—C10'−0.5 (4)
C14—C1—C2—C3−177.0 (3)C9'—C8'—C13'—C14'−179.7 (2)
C2—C1—C14—C152.6 (4)C8'—C9'—C10'—C11'1.6 (5)
C6—C1—C14—C13−1.1 (3)C9'—C10'—C11'—C12'−1.2 (5)
C6—C1—C2—C31.8 (4)C10'—C11'—C12'—C13'−0.3 (5)
C2—C1—C14—C13177.7 (2)C11'—C12'—C13'—C14'−179.9 (2)
C14—C1—C6—C5178.6 (3)C11'—C12'—C13'—C8'1.3 (4)
C1—C2—C3—C4−2.7 (5)C8'—C13'—C14'—C15'−177.4 (2)
C2—C3—C4—C51.9 (6)C12'—C13'—C14'—C15'3.9 (3)
C3—C4—C5—C6−0.4 (6)C8'—C13'—C14'—C1'2.8 (3)
C4—C5—C6—C7176.7 (3)C12'—C13'—C14'—C1'−175.9 (2)
C4—C5—C6—C1−0.3 (5)C13'—C14'—C15'—N1'160.0 (2)
C5—C6—C7—C8−177.6 (3)C1'—C14'—C15'—C16'85.7 (3)
C1—C6—C7—C8−0.5 (4)C13'—C14'—C15'—C16'−94.0 (2)
C6—C7—C8—C9178.8 (3)C1'—C14'—C15'—N1'−20.3 (3)
C6—C7—C8—C13−0.9 (4)N1'—C15'—C16'—C17'120.49 (18)
C9—C8—C13—C14−178.4 (2)C14'—C15'—C16'—C17'−3.4 (3)
C13—C8—C9—C10−0.3 (4)N1'—C15'—C16'—C28'−111.67 (18)
C7—C8—C9—C10−180.0 (3)C14'—C15'—C16'—C29'−121.76 (19)
C7—C8—C13—C12−178.6 (3)N1'—C15'—C16'—C29'2.15 (15)
C9—C8—C13—C121.8 (4)C14'—C15'—C16'—C28'124.4 (2)
C7—C8—C13—C141.3 (4)C15'—C16'—C28'—C23'−101.0 (2)
C8—C9—C10—C11−0.7 (5)C29'—C16'—C28'—C23'165.8 (2)
C9—C10—C11—C120.2 (5)C29'—C16'—C28'—C27'−17.5 (3)
C10—C11—C12—C131.4 (4)C29'—C16'—C17'—C18'19.7 (3)
C11—C12—C13—C14177.8 (3)C29'—C16'—C17'—C22'−160.4 (2)
C11—C12—C13—C8−2.3 (4)C15'—C16'—C28'—C27'75.7 (3)
C8—C13—C14—C15175.4 (2)C17'—C16'—C28'—C23'31.3 (3)
C12—C13—C14—C15−4.8 (3)C17'—C16'—C28'—C27'−152.0 (2)
C12—C13—C14—C1179.5 (2)C15'—C16'—C17'—C18'−78.5 (3)
C8—C13—C14—C1−0.3 (3)C28'—C16'—C17'—C22'−27.7 (3)
C13—C14—C15—C16104.5 (2)C15'—C16'—C17'—C22'101.5 (2)
C1—C14—C15—C16−80.0 (3)C15'—C16'—C29'—O2'178.5 (3)
C13—C14—C15—N1−149.0 (2)C17'—C16'—C29'—O2'60.2 (4)
C1—C14—C15—N126.4 (3)C17'—C16'—C29'—N1'−120.7 (2)
C14—C15—C16—C175.6 (3)C15'—C16'—C29'—N1'−2.36 (17)
N1—C15—C16—C28114.2 (2)C28'—C16'—C17'—C18'152.4 (2)
N1—C15—C16—C17−117.6 (2)C28'—C16'—C29'—N1'109.0 (2)
C14—C15—C16—C28−122.6 (2)C28'—C16'—C29'—O2'−70.1 (4)
N1—C15—C16—C29−0.10 (15)C16'—C17'—C22'—C21'−178.9 (2)
C14—C15—C16—C29123.1 (2)C18'—C17'—C22'—O1'−178.6 (2)
C29—C16—C28—C2714.5 (3)C16'—C17'—C22'—O1'1.4 (3)
C15—C16—C29—O2179.9 (3)C18'—C17'—C22'—C21'1.1 (4)
C28—C16—C17—C2232.9 (3)C22'—C17'—C18'—C19'−1.8 (3)
C17—C16—C28—C23−36.0 (3)C16'—C17'—C18'—C19'178.2 (2)
C29—C16—C28—C23−169.9 (2)C17'—C18'—C19'—C20'0.4 (4)
C17—C16—C28—C27148.4 (2)C18'—C19'—C20'—C21'1.8 (4)
C28—C16—C29—N1−110.0 (2)C19'—C20'—C21'—C22'−2.4 (4)
C29—C16—C17—C18−12.1 (3)C20'—C21'—C22'—O1'−179.3 (2)
C15—C16—C17—C22−95.7 (3)C20'—C21'—C22'—C17'0.9 (4)
C15—C16—C28—C27−78.8 (3)C24'—C23'—C28'—C16'171.0 (2)
C15—C16—C17—C1886.5 (3)C24'—C23'—C28'—C27'−5.9 (4)
C17—C16—C29—O2−60.8 (3)O1'—C23'—C28'—C16'−8.6 (3)
C17—C16—C29—N1119.4 (2)O1'—C23'—C28'—C27'174.5 (2)
C28—C16—C29—O269.8 (4)C28'—C23'—C24'—C25'3.9 (4)
C29—C16—C17—C22165.8 (2)O1'—C23'—C24'—C25'−176.5 (2)
C15—C16—C29—N10.11 (16)C23'—C24'—C25'—C26'1.5 (4)
C15—C16—C28—C2396.9 (3)C24'—C25'—C26'—C27'−4.6 (5)
C28—C16—C17—C18−144.9 (3)C25'—C26'—C27'—C28'2.5 (4)
C16—C17—C18—C19179.9 (3)C26'—C27'—C28'—C23'2.6 (4)
C18—C17—C22—O1176.0 (3)C26'—C27'—C28'—C16'−174.1 (2)
C16—C17—C22—O1−2.0 (4)N1'—C30'—C31'—C32'178.5 (2)
C22—C17—C18—C192.1 (4)C35'—C30'—C31'—O3'177.1 (2)
C16—C17—C22—C21179.1 (3)C35'—C30'—C31'—C32'−2.1 (4)
C18—C17—C22—C21−2.9 (4)N1'—C30'—C35'—C34'−179.7 (2)
C17—C18—C19—C20−0.2 (5)C31'—C30'—C35'—C34'0.9 (4)
C18—C19—C20—C21−1.0 (6)N1'—C30'—C31'—O3'−2.3 (3)
C19—C20—C21—C220.2 (6)O3'—C31'—C32'—C33'−177.2 (2)
C20—C21—C22—O1−177.2 (3)C30'—C31'—C32'—C33'1.9 (4)
C20—C21—C22—C171.8 (5)C31'—C32'—C33'—C34'−0.4 (4)
C24—C23—C28—C274.5 (4)C31'—C32'—C33'—O4'179.9 (2)
O1—C23—C24—C25178.1 (3)O4'—C33'—C34'—C35'178.8 (2)
O1—C23—C28—C168.1 (4)C32'—C33'—C34'—C35'−0.9 (4)
O1—C23—C28—C27−175.9 (2)C33'—C34'—C35'—C30'0.6 (4)

Symmetry codes: (i) x, y, z+1; (ii) −x+1, −y+1, −z; (iii) −x+2, −y+1, −z; (iv) −x+2, −y+2, −z; (v) −x+1, −y+1, −z+1; (vi) x+1, y, z; (vii) x−1, y−1, z; (viii) −x, −y, −z+1; (ix) −x, −y+1, −z; (x) −x+1, −y, −z+1; (xi) x, y, z−1; (xii) x−1, y, z; (xiii) −x, −y+1, −z+1; (xiv) x, y−1, z+1; (xv) x, y+1, z−1; (xvi) x+1, y+1, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···N10.932.332.964 (3)125
C2'—H2'···N1'0.932.312.957 (3)126
C3—H3···O4'ix0.932.593.484 (4)163
C9—H9···O1iv0.932.563.458 (4)164
C35—H35···O20.932.583.132 (3)119
C35—H35···O2ii0.932.523.212 (3)131
C35'—H35'···O2'0.932.523.106 (3)121
C2—H2···Cg10.932.593.188 (3)122
C2'—H2'···Cg150.932.623.196 (3)121
C25'—H25'···Cg22viii0.932.983.791 (3)147

Symmetry codes: (ix) −x, −y+1, −z; (iv) −x+2, −y+2, −z; (ii) −x+1, −y+1, −z; (viii) −x, −y, −z+1.

Table 2 Comparision of the dihedral angles between the planes of the rings for molecules IA and IB.

(The prime suffix shows the similar planes and angles for the molecule IB).

Plane1Plane2Angle(1/2)Angle(1'/2')
AB80.83 (16)81.34 (15)
AC67.20 (17)72.70 (15)
AD67.97 (13)65.71 (13)
AE22.23 (14)20.88 (15)
BC32.34 (16)26.90 (13)
BD46.25 (12)41.50 (10)
BE77.80 (13)79.39 (13)
CD67.09 (13)62.22 (9)
CE45.50 (14)52.74 (12)
DE79.35 (9)76.25 (10)

The planes of the molecule IA are A(N1/C15/C16/C29), B(C23–C28), C(C17–C22), D(C1–C14) and E(C30–C35) .

Table 3 The dihedral angles between the similar ring planes in molecules IA and IB

PlanePlaneAngle
AA'86.92 (17)
BB'46.81 (14)
CC'88.40 (14)
DD'54.64 (6)
EE'65.35 (12)

The planes of the molecule IB are A'(N1'/C15'/C16'/C29'), B'(C23'–C28'), C'(C17'–C22'), D'(C1'–C14') and E'(C30'–C35').

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2470).

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