organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(2RS,3SR,10SR,11RS)-3,10-Diphen­­oxy-18,21-dioxa-5,8-di­aza­penta­cyclo­[20.4.0.02,5.08,11.012,17]hexa­cosa-1(26),12,14,16,22,24-hexa­ene-4,9-dione ethyl acetate hemisolvate

aDepartment of Physics, The Madura College, Madurai 625 011, India, bDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
*Correspondence e-mail: plakshmannilantha@ymail.com

(Received 22 July 2011; accepted 26 July 2011; online 30 July 2011)

In the title compound, C34H30N2O6·0.5C4H8O2, there are two mol­ecules in the asymmetric unit and the structure is stabilized by C—H⋯O inter­actions. The two nonsolvent mol­ecules of the asymmetric unit are linked together by a weak C—H⋯O hydrogen bond. The ethyl acetate mol­ecule is present as a space filler and does not participate in the hydrogen-bonding network.

Related literature

For background to the pharmaceutical applications of β-lactam anti­biotics, see: Samarendra et al. (1994[Samarendra, C. I., Maiti, N., Micetich, R., Daneshtalab, M., Atchison, K., Phillips, O. A. & Kunugita, C. (1994). J. Antibiot. 47, 1030-1040.]); Vaccaro & Davis (1998[Vaccaro, W. D. & Davis, H. R. Jr (1998). Bioorg. Med. Chem. Lett. 8, 313-318.]); Vaccaro et al. (1998[Vaccaro, W. D., Sher, R. & Davis, H. R. Jr (1998). Bioorg. Med. Chem. Lett. 8, 35-40.]); Borthwick et al. (1998[Borthwick, A. D., Weingarte, G., Haley, T. M., Tomaszewski, M., Wang, W., Hu, Z., Bedard, J., Jin, H., Yuen, L. & Mansour, T. S. (1998). Bioorg. Med. Chem. Lett. 8, 365-370.]).

[Scheme 1]

Experimental

Crystal data
  • C34H30N2O6·0.5(C4H8O2)

  • Mr = 606.65

  • Monoclinic, P 21 /n

  • a = 18.037 (3) Å

  • b = 17.201 (3) Å

  • c = 21.589 (4) Å

  • β = 108.722 (1)°

  • V = 6343.67 (19) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.18 × 0.16 × 0.13 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker (1998). SADABS. Bruker AXS Inc., Maddison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.988

  • 64493 measured reflections

  • 13208 independent reflections

  • 7192 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.053

  • wR(F2) = 0.175

  • S = 1.02

  • 13208 reflections

  • 813 parameters

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C53—H53⋯O6 0.93 2.52 3.344 (3) 147
C2—H2⋯O2 0.93 2.42 3.250 (3) 149
C32—H32⋯O1 0.93 2.33 3.178 (3) 151
C66—H66⋯O7 0.93 2.48 3.299 (3) 147

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

β-Lactam antibiotics are widely employed in the treatment of bacterial infections(Samarendra et al., 1994). In recent years, several natural β-lactams have been shown to exhibit a high antibacterial activity. 1,3,4-trisubstituted β-lactams were found to be new, potent cholesterol absorption inhibitors (Vaccaro & Davis 1998; Vaccaro et al., 1998) human cytomegalovirus (Borthwick et al., 1998). Furthermore, many anticancer drugs in current use are toxic and thus limited in their efficacy. It is therefore essential to develop novel chemotherapeutic agents with lower levels of toxicity. β-lactam antibiotics have been used for many years with limited or no toxicity. In view of this, the crystal structure determination of the title compound was carried out.

The asymmetric unit of (I) contain two independent molecules, The pair have almost identical geometry. The internal angles of the four-membered rings of the title compound, (I), vary from 85.3 (8) to 96.2 (5)° . The sums of the bond angles at the N atoms are 359.4 (2) and 360.0 (1),359.3 (8) 359.9 (5) for N1, N2,N3 and N4 respectively are in accordance with sp2 hybridization. The conformation of the molecules is stabilized by weak intramolecular C—H···O and C—H···N interactions, (Table 1). The two non-solvent molecules of the asymmetruc unit are linked together by a weak C—H···O hydrogen bond. The presence of the ethyl acetate solvent as a mere space filler suggests that its contribution to the intermolecular interactions is insignificant but it has nevertheless played a role in crystallization. There is a solvent accessible void of 66.7 Å3 in the structure.

Related literature top

For background to the pharmaceutical applications of β-lactam antibiotics, see: Samarendra et al. (1994); Vaccaro & Davis (1998); Vaccaro et al. (1998); Borthwick et al. (1998).

Experimental top

A solution of phenoxyacetyl chloride in dry dichloromethane (20 ml) was slowly added to a solution of bisimine (1 mmol) and Et3N (3.5 mmol) in dichloromethane (20 ml) at 0 °C and the reaction mixture was stirred for 12 h at room temperature. Completion of the reaction evidenced by TLC analysis, the reaction mixture was washed with water (2 X 20 ml), saturated NaHCO3 (15 ml) and brine (15 ml). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was separated by column chromatography (hexane: ethyl acetate 7:3) gave pure bis-β-lactam in good yield. The product was recrystallized from ethyl acetate by slow evaporation technique. m.p.: 195°C, yield: 48%

Refinement top

The H atoms were placed in calculated positions and allowed to ride on their carrier atoms with C—H = 0.93–0.98 Å and Uiso = 1.2Ueq(C,) for CH, CH2 groups and Uiso = 1.5Ueq(C) for CH3 group.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. One of the molecule of the two independent molecules and the solvent molecule ethyl acetate of the asymmetric unit(I), showing 10% probability displacement ellipsoids and the atom-numbering scheme. H-atoms are omitted for clarity.
[Figure 2] Fig. 2. The other molecule of the two independent molecules of the asymmetric unit(I), showing 10% probability displacement ellipsoids and the atom-numbering scheme. H-atoms are omitted for clarity.
(2RS,3SR,10SR,11RS)-3,10-Diphenoxy-18,21-dioxa-5,8- diazapentacyclo[20.4.0.02,5.08,11.012,17]hexacosa- 1(26),12,14,16,22,24-hexaene-4,9-dione ethyl acetate hemisolvate top
Crystal data top
C34H30N2O6·0.5(C4H8O2)F(000) = 2560
Mr = 606.65Dx = 1.270 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 2500 reflections
a = 18.037 (3) Åθ = 2–27°
b = 17.201 (3) ŵ = 0.09 mm1
c = 21.589 (4) ÅT = 293 K
β = 108.722 (10)°Block, colourless
V = 6343.67 (19) Å30.18 × 0.16 × 0.13 mm
Z = 8
Data collection top
Bruker SMART APEX CCD
diffractometer
13208 independent reflections
Radiation source: fine-focus sealed tube7192 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω scansθmax = 26.6°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 2222
Tmin = 0.984, Tmax = 0.988k = 2121
64493 measured reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0801P)2 + 1.3813P]
where P = (Fo2 + 2Fc2)/3
13208 reflections(Δ/σ)max < 0.001
813 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C34H30N2O6·0.5(C4H8O2)V = 6343.67 (19) Å3
Mr = 606.65Z = 8
Monoclinic, P21/nMo Kα radiation
a = 18.037 (3) ŵ = 0.09 mm1
b = 17.201 (3) ÅT = 293 K
c = 21.589 (4) Å0.18 × 0.16 × 0.13 mm
β = 108.722 (10)°
Data collection top
Bruker SMART APEX CCD
diffractometer
13208 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
7192 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.988Rint = 0.046
64493 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 1.02Δρmax = 0.32 e Å3
13208 reflectionsΔρmin = 0.24 e Å3
813 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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) top
xyzUiso*/Ueq
O10.58820 (10)0.50849 (11)0.49402 (8)0.0675 (5)
O20.46252 (10)0.40807 (11)0.76094 (9)0.0678 (5)
O30.79089 (11)0.27095 (10)0.67869 (9)0.0692 (5)
O40.68980 (10)0.18393 (11)0.72407 (9)0.0723 (5)
O50.75451 (8)0.41331 (10)0.52020 (7)0.0543 (4)
O60.54253 (9)0.23356 (9)0.79798 (7)0.0546 (4)
N10.53463 (10)0.36778 (11)0.69396 (9)0.0482 (5)
N20.62448 (10)0.43556 (11)0.59046 (8)0.0477 (5)
C10.53443 (14)0.23039 (16)0.85949 (11)0.0579 (7)
C20.50667 (17)0.29204 (19)0.88634 (13)0.0738 (8)
H20.49380.33870.86360.089*
C30.49799 (19)0.2840 (2)0.94753 (15)0.0934 (11)
H30.47900.32530.96580.112*
C40.5172 (2)0.2159 (3)0.98101 (16)0.1071 (14)
H40.51240.21101.02250.129*
C50.5436 (2)0.1545 (3)0.95333 (17)0.1107 (13)
H50.55550.10780.97600.133*
C60.55309 (18)0.16067 (19)0.89231 (14)0.0805 (9)
H60.57150.11900.87400.097*
C70.56993 (12)0.30462 (13)0.78045 (10)0.0451 (5)
H70.61430.32520.81600.054*
C80.58797 (12)0.30110 (13)0.71428 (10)0.0438 (5)
H80.64230.31530.71970.053*
C90.51115 (12)0.36898 (14)0.74746 (11)0.0481 (6)
C100.56317 (14)0.22914 (14)0.67387 (10)0.0501 (6)
C110.48777 (17)0.2166 (2)0.63373 (13)0.0766 (8)
H110.44990.25450.63020.092*
C120.4673 (2)0.1484 (3)0.59849 (16)0.1033 (12)
H120.41580.14050.57210.124*
C130.5221 (3)0.0930 (2)0.60227 (17)0.1031 (12)
H130.50790.04770.57780.124*
C140.5990 (2)0.10279 (18)0.64218 (15)0.0818 (9)
H140.63650.06490.64440.098*
C150.61848 (16)0.17077 (15)0.67866 (12)0.0593 (6)
C160.75889 (17)0.15158 (17)0.71566 (17)0.0795 (9)
H16A0.74820.13320.67120.095*
H16B0.77760.10820.74530.095*
C170.81814 (16)0.21491 (17)0.73031 (15)0.0751 (8)
H17A0.82310.23850.77220.090*
H17B0.86880.19460.73170.090*
C180.81363 (13)0.34669 (15)0.69163 (10)0.0488 (6)
C190.88309 (14)0.36788 (17)0.73889 (11)0.0582 (7)
H190.91570.33010.76450.070*
C200.90333 (15)0.4447 (2)0.74750 (13)0.0669 (8)
H200.94980.45890.77930.080*
C210.85609 (17)0.50128 (18)0.70996 (13)0.0675 (7)
H210.87040.55340.71610.081*
C220.78640 (15)0.47960 (15)0.66253 (11)0.0559 (6)
H220.75430.51770.63700.067*
C230.76414 (12)0.40245 (13)0.65274 (10)0.0426 (5)
C240.68875 (12)0.37855 (13)0.60175 (10)0.0439 (5)
H240.67250.32590.60900.053*
C250.68248 (12)0.39336 (14)0.52855 (10)0.0466 (5)
H250.65700.35000.50020.056*
C260.62359 (12)0.45784 (15)0.53028 (10)0.0482 (6)
C270.75411 (12)0.42248 (14)0.45610 (10)0.0476 (5)
C280.81786 (15)0.39355 (18)0.44128 (12)0.0685 (8)
H280.85770.36790.47300.082*
C290.82196 (16)0.40302 (18)0.37899 (13)0.0721 (8)
H290.86490.38370.36900.087*
C300.76339 (15)0.44063 (16)0.33156 (12)0.0611 (7)
H300.76620.44620.28950.073*
C310.70102 (14)0.46967 (15)0.34697 (11)0.0546 (6)
H310.66150.49570.31520.066*
C320.69594 (13)0.46082 (14)0.40911 (11)0.0507 (6)
H320.65320.48080.41900.061*
C330.58264 (13)0.46822 (14)0.63199 (11)0.0504 (6)
H33A0.56240.51880.61490.061*
H33B0.61950.47600.67550.061*
C340.51501 (12)0.41862 (15)0.63752 (11)0.0526 (6)
H34A0.47290.45280.63910.063*
H34B0.49560.38710.59830.063*
O70.08612 (10)0.03084 (12)0.50260 (9)0.0732 (6)
O80.02514 (11)0.08467 (11)0.77821 (10)0.0750 (5)
O90.27029 (12)0.22602 (11)0.67684 (9)0.0814 (6)
O100.18251 (14)0.31822 (12)0.73090 (10)0.0873 (6)
O110.23893 (8)0.08131 (10)0.51517 (7)0.0545 (4)
O120.05351 (10)0.25116 (10)0.81692 (8)0.0634 (5)
N30.03988 (10)0.12389 (12)0.70535 (9)0.0516 (5)
N40.11730 (10)0.05203 (11)0.59366 (8)0.0495 (5)
C350.10712 (19)0.29037 (16)0.86937 (13)0.0687 (7)
C360.0732 (3)0.33826 (19)0.90397 (16)0.1016 (12)
H360.01910.34330.89250.122*
C370.1232 (4)0.3788 (3)0.9568 (2)0.146 (2)
H370.10170.41260.98010.176*
C380.2030 (4)0.3706 (3)0.9758 (3)0.158 (2)
H380.23520.39671.01230.190*
C390.2332 (3)0.3238 (3)0.9400 (2)0.1273 (15)
H390.28730.31840.95200.153*
C400.1864 (2)0.2834 (2)0.88599 (16)0.0918 (10)
H400.20870.25220.86160.110*
C410.08090 (14)0.18611 (14)0.79130 (11)0.0506 (6)
H410.12790.16420.82320.061*
C420.09050 (13)0.19243 (13)0.72190 (11)0.0471 (5)
H420.14410.18110.72280.057*
C430.02096 (14)0.12327 (14)0.76097 (11)0.0521 (6)
C440.05858 (15)0.26504 (16)0.68418 (11)0.0562 (6)
C450.01947 (17)0.2737 (2)0.64774 (13)0.0765 (9)
H450.05400.23260.64480.092*
C460.0471 (2)0.3434 (3)0.61535 (15)0.1036 (14)
H460.10000.34910.59210.124*
C470.0032 (3)0.4026 (3)0.61783 (17)0.1100 (15)
H470.01490.44790.59440.132*
C480.0809 (3)0.39636 (19)0.65468 (16)0.1004 (12)
H480.11490.43770.65710.120*
C490.1083 (2)0.32766 (17)0.68836 (13)0.0713 (8)
C500.2471 (2)0.34862 (19)0.71346 (19)0.0998 (11)
H50A0.26980.39300.74060.120*
H50B0.22990.36500.66810.120*
C510.3058 (2)0.2846 (2)0.72398 (17)0.0935 (10)
H51A0.35350.30340.71770.112*
H51B0.31840.26400.76800.112*
C520.30210 (13)0.15310 (15)0.68510 (11)0.0536 (6)
C530.37626 (15)0.1362 (2)0.72771 (13)0.0705 (8)
H530.40730.17570.75220.085*
C540.40356 (16)0.0618 (2)0.73372 (14)0.0803 (9)
H540.45310.05080.76250.096*
C550.35892 (18)0.0031 (2)0.69790 (13)0.0774 (9)
H550.37800.04760.70200.093*
C560.28482 (15)0.01966 (16)0.65534 (11)0.0592 (6)
H560.25420.02040.63130.071*
C570.25554 (12)0.09451 (13)0.64801 (10)0.0427 (5)
C580.17667 (12)0.11307 (13)0.59957 (10)0.0436 (5)
H580.15800.16520.60550.052*
C590.16737 (12)0.09423 (14)0.52655 (10)0.0474 (5)
H590.13600.13380.49690.057*
C600.11648 (13)0.02564 (16)0.53458 (11)0.0522 (6)
C610.23611 (12)0.07508 (14)0.45046 (10)0.0461 (5)
C620.29714 (16)0.10742 (19)0.43439 (13)0.0752 (9)
H620.33670.13390.46580.090*
C630.29951 (17)0.10048 (19)0.37165 (13)0.0788 (9)
H630.34090.12250.36090.095*
C640.24212 (15)0.06174 (15)0.32478 (11)0.0571 (6)
H640.24430.05740.28250.069*
C650.18145 (14)0.02940 (14)0.34073 (11)0.0516 (6)
H650.14220.00280.30920.062*
C660.17816 (13)0.03615 (14)0.40402 (10)0.0489 (6)
H660.13670.01430.41470.059*
C670.08087 (14)0.02224 (15)0.63947 (12)0.0567 (6)
H67A0.12100.01530.68150.068*
H67B0.05910.02860.62460.068*
C680.01636 (13)0.07316 (17)0.64897 (12)0.0628 (7)
H68A0.00500.10490.61010.075*
H68B0.02530.03970.65260.075*
O130.64589 (13)0.69087 (14)0.51650 (12)0.1002 (7)
O140.67151 (18)0.64668 (18)0.61737 (13)0.1269 (9)
C690.5398 (2)0.6845 (2)0.5557 (2)0.1183 (13)
H69A0.51120.64310.52850.178*
H69B0.52380.73330.53400.178*
H69C0.52930.68430.59650.178*
C700.6249 (2)0.6732 (2)0.56792 (18)0.0894 (10)
C710.7275 (2)0.6741 (3)0.5224 (2)0.1394 (17)
H71A0.76260.70590.55640.167*
H71B0.73940.61980.53330.167*
C720.7356 (3)0.6917 (4)0.4603 (3)0.187 (3)
H72A0.69790.66250.42680.280*
H72B0.78740.67820.46070.280*
H72C0.72700.74630.45150.280*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0629 (10)0.0937 (14)0.0532 (10)0.0301 (10)0.0288 (8)0.0327 (10)
O20.0679 (11)0.0809 (13)0.0716 (12)0.0114 (10)0.0459 (10)0.0080 (10)
O30.0805 (12)0.0558 (12)0.0588 (11)0.0143 (10)0.0050 (9)0.0102 (9)
O40.0673 (11)0.0669 (12)0.0752 (13)0.0155 (9)0.0121 (10)0.0115 (10)
O50.0451 (8)0.0895 (12)0.0327 (8)0.0076 (8)0.0188 (7)0.0068 (8)
O60.0673 (10)0.0610 (10)0.0375 (8)0.0207 (8)0.0196 (7)0.0042 (7)
N10.0469 (10)0.0603 (12)0.0444 (11)0.0092 (9)0.0243 (8)0.0148 (9)
N20.0472 (10)0.0637 (12)0.0382 (10)0.0142 (9)0.0219 (8)0.0149 (9)
C10.0575 (14)0.0792 (19)0.0360 (13)0.0279 (13)0.0135 (11)0.0048 (13)
C20.0846 (19)0.093 (2)0.0494 (16)0.0148 (17)0.0288 (14)0.0006 (15)
C30.103 (2)0.133 (3)0.0557 (19)0.039 (2)0.0420 (17)0.010 (2)
C40.121 (3)0.161 (4)0.0485 (19)0.064 (3)0.0388 (19)0.002 (2)
C50.145 (3)0.122 (3)0.065 (2)0.044 (3)0.033 (2)0.030 (2)
C60.099 (2)0.083 (2)0.0595 (18)0.0216 (18)0.0262 (16)0.0180 (16)
C70.0476 (12)0.0528 (14)0.0373 (12)0.0109 (11)0.0171 (9)0.0042 (10)
C80.0429 (11)0.0527 (14)0.0388 (12)0.0010 (10)0.0173 (9)0.0097 (10)
C90.0450 (12)0.0607 (15)0.0455 (13)0.0054 (11)0.0242 (10)0.0057 (11)
C100.0571 (14)0.0587 (15)0.0357 (12)0.0058 (12)0.0168 (10)0.0061 (11)
C110.0685 (17)0.097 (2)0.0555 (17)0.0120 (16)0.0076 (14)0.0075 (16)
C120.102 (3)0.122 (3)0.065 (2)0.032 (3)0.0015 (18)0.015 (2)
C130.146 (4)0.083 (3)0.068 (2)0.034 (3)0.016 (2)0.0200 (19)
C140.118 (3)0.0595 (19)0.0642 (19)0.0030 (18)0.0242 (18)0.0039 (15)
C150.0758 (17)0.0550 (16)0.0455 (14)0.0040 (14)0.0169 (13)0.0033 (12)
C160.083 (2)0.0571 (18)0.100 (2)0.0284 (16)0.0317 (17)0.0122 (16)
C170.0671 (17)0.0720 (19)0.081 (2)0.0288 (16)0.0170 (15)0.0269 (16)
C180.0508 (13)0.0615 (16)0.0386 (12)0.0093 (12)0.0209 (10)0.0029 (11)
C190.0480 (13)0.085 (2)0.0441 (14)0.0124 (13)0.0180 (11)0.0007 (13)
C200.0535 (15)0.104 (2)0.0479 (15)0.0090 (16)0.0226 (12)0.0068 (15)
C210.0807 (19)0.0758 (19)0.0549 (16)0.0181 (16)0.0343 (15)0.0066 (15)
C220.0660 (15)0.0625 (17)0.0456 (14)0.0029 (13)0.0268 (12)0.0063 (12)
C230.0492 (12)0.0527 (14)0.0335 (11)0.0052 (11)0.0237 (10)0.0066 (10)
C240.0487 (12)0.0501 (13)0.0368 (12)0.0055 (10)0.0193 (10)0.0067 (10)
C250.0458 (12)0.0620 (15)0.0340 (11)0.0037 (11)0.0157 (9)0.0049 (10)
C260.0426 (12)0.0682 (16)0.0375 (12)0.0073 (11)0.0182 (10)0.0117 (11)
C270.0485 (12)0.0650 (15)0.0334 (12)0.0013 (11)0.0191 (10)0.0009 (11)
C280.0596 (15)0.105 (2)0.0479 (15)0.0214 (15)0.0276 (12)0.0132 (14)
C290.0701 (17)0.102 (2)0.0581 (17)0.0154 (16)0.0402 (14)0.0052 (15)
C300.0754 (17)0.0769 (18)0.0411 (14)0.0081 (14)0.0327 (13)0.0011 (13)
C310.0622 (15)0.0638 (16)0.0398 (13)0.0039 (12)0.0193 (11)0.0055 (11)
C320.0508 (13)0.0649 (16)0.0410 (13)0.0046 (12)0.0211 (10)0.0044 (11)
C330.0545 (13)0.0589 (15)0.0471 (13)0.0135 (11)0.0293 (11)0.0126 (11)
C340.0445 (12)0.0699 (16)0.0481 (13)0.0143 (11)0.0216 (10)0.0211 (12)
O70.0749 (12)0.0944 (14)0.0594 (11)0.0356 (11)0.0341 (9)0.0355 (10)
O80.0878 (13)0.0758 (13)0.0845 (14)0.0058 (11)0.0600 (11)0.0011 (10)
O90.0924 (14)0.0577 (13)0.0716 (13)0.0242 (11)0.0050 (10)0.0041 (10)
O100.1087 (16)0.0700 (13)0.0707 (14)0.0264 (12)0.0113 (12)0.0074 (11)
O110.0440 (8)0.0917 (13)0.0311 (8)0.0079 (8)0.0167 (6)0.0012 (8)
O120.0800 (11)0.0635 (11)0.0474 (10)0.0159 (9)0.0216 (9)0.0108 (8)
N30.0498 (11)0.0667 (13)0.0455 (11)0.0117 (10)0.0253 (9)0.0141 (9)
N40.0491 (10)0.0665 (13)0.0386 (10)0.0179 (9)0.0223 (8)0.0150 (9)
C350.103 (2)0.0580 (17)0.0463 (15)0.0021 (16)0.0264 (15)0.0010 (13)
C360.167 (3)0.077 (2)0.073 (2)0.003 (2)0.057 (2)0.0237 (18)
C370.249 (6)0.098 (3)0.100 (4)0.018 (4)0.066 (4)0.048 (3)
C380.229 (7)0.122 (4)0.094 (4)0.050 (5)0.012 (4)0.036 (3)
C390.138 (4)0.112 (3)0.104 (3)0.036 (3)0.000 (3)0.011 (3)
C400.104 (3)0.084 (2)0.075 (2)0.008 (2)0.0113 (19)0.0140 (18)
C410.0604 (14)0.0524 (14)0.0397 (13)0.0122 (11)0.0171 (11)0.0046 (11)
C420.0459 (12)0.0529 (14)0.0460 (13)0.0001 (11)0.0196 (10)0.0070 (11)
C430.0567 (14)0.0582 (15)0.0508 (14)0.0069 (12)0.0304 (11)0.0009 (11)
C440.0662 (16)0.0708 (18)0.0381 (13)0.0129 (14)0.0256 (11)0.0018 (12)
C450.0727 (18)0.117 (3)0.0509 (16)0.0300 (18)0.0350 (14)0.0157 (16)
C460.113 (3)0.161 (4)0.0489 (18)0.076 (3)0.0432 (19)0.030 (2)
C470.184 (5)0.101 (3)0.053 (2)0.066 (3)0.048 (3)0.018 (2)
C480.183 (4)0.055 (2)0.058 (2)0.014 (2)0.032 (2)0.0022 (16)
C490.107 (2)0.0581 (18)0.0475 (16)0.0031 (17)0.0233 (16)0.0022 (13)
C500.130 (3)0.061 (2)0.105 (3)0.048 (2)0.034 (2)0.0126 (19)
C510.097 (2)0.073 (2)0.097 (3)0.045 (2)0.0135 (19)0.0191 (19)
C520.0526 (14)0.0641 (17)0.0454 (14)0.0168 (12)0.0172 (11)0.0019 (12)
C530.0490 (15)0.107 (3)0.0533 (16)0.0250 (16)0.0127 (12)0.0007 (16)
C540.0500 (16)0.137 (3)0.0536 (17)0.0135 (19)0.0158 (13)0.0057 (19)
C550.084 (2)0.101 (2)0.0478 (16)0.0341 (19)0.0209 (15)0.0052 (16)
C560.0702 (16)0.0669 (18)0.0413 (13)0.0053 (13)0.0189 (12)0.0057 (12)
C570.0461 (12)0.0563 (15)0.0304 (11)0.0085 (11)0.0188 (9)0.0011 (10)
C580.0445 (12)0.0527 (14)0.0359 (11)0.0063 (10)0.0163 (9)0.0038 (10)
C590.0430 (12)0.0665 (16)0.0340 (12)0.0027 (11)0.0143 (9)0.0018 (11)
C600.0435 (12)0.0775 (18)0.0381 (12)0.0106 (12)0.0167 (10)0.0148 (12)
C610.0471 (12)0.0612 (15)0.0330 (11)0.0030 (11)0.0169 (10)0.0027 (10)
C620.0686 (17)0.114 (2)0.0489 (15)0.0386 (17)0.0273 (13)0.0134 (15)
C630.0793 (19)0.116 (3)0.0559 (17)0.0335 (18)0.0419 (15)0.0120 (16)
C640.0710 (16)0.0698 (17)0.0387 (13)0.0068 (13)0.0291 (12)0.0011 (12)
C650.0555 (13)0.0596 (15)0.0407 (13)0.0043 (12)0.0171 (10)0.0047 (11)
C660.0466 (12)0.0619 (15)0.0415 (13)0.0039 (11)0.0188 (10)0.0009 (11)
C670.0663 (15)0.0621 (16)0.0539 (14)0.0193 (12)0.0365 (12)0.0153 (12)
C680.0493 (13)0.091 (2)0.0537 (15)0.0201 (13)0.0249 (11)0.0268 (14)
O130.0974 (16)0.1138 (19)0.0950 (17)0.0069 (14)0.0389 (13)0.0220 (14)
O140.144 (2)0.143 (3)0.0833 (18)0.0065 (19)0.0226 (17)0.0098 (17)
C690.123 (3)0.116 (3)0.137 (4)0.025 (3)0.071 (3)0.013 (3)
C700.117 (3)0.080 (2)0.073 (2)0.003 (2)0.032 (2)0.0031 (18)
C710.096 (3)0.187 (5)0.148 (4)0.013 (3)0.056 (3)0.046 (4)
C720.139 (4)0.261 (7)0.190 (6)0.011 (4)0.094 (4)0.060 (5)
Geometric parameters (Å, º) top
O1—C261.208 (3)O11—C591.407 (2)
O2—C91.213 (3)O12—C351.403 (3)
O3—C181.368 (3)O12—C411.406 (3)
O3—C171.436 (3)N3—C431.350 (3)
O4—C151.363 (3)N3—C681.446 (3)
O4—C161.428 (3)N3—C421.463 (3)
O5—C271.390 (2)N4—C601.349 (3)
O5—C251.410 (2)N4—C671.446 (3)
O6—C11.383 (3)N4—C581.476 (3)
O6—C71.415 (2)C35—C401.364 (4)
N1—C91.352 (3)C35—C361.380 (4)
N1—C341.448 (3)C36—C371.394 (6)
N1—C81.471 (3)C36—H360.9300
N2—C261.350 (3)C37—C381.370 (7)
N2—C331.457 (3)C37—H370.9300
N2—C241.478 (3)C38—C391.346 (7)
C1—C21.377 (4)C38—H380.9300
C1—C61.379 (4)C39—C401.387 (5)
C2—C31.386 (4)C39—H390.9300
C2—H20.9300C40—H400.9300
C3—C41.362 (5)C41—C431.520 (3)
C3—H30.9300C41—C421.566 (3)
C4—C51.373 (5)C41—H410.9800
C4—H40.9300C42—C441.501 (3)
C5—C61.386 (4)C42—H420.9800
C5—H50.9300C44—C451.383 (4)
C6—H60.9300C44—C491.385 (4)
C7—C91.540 (3)C45—C461.397 (5)
C7—C81.565 (3)C45—H450.9300
C7—H70.9800C46—C471.355 (6)
C8—C101.498 (3)C46—H460.9300
C8—H80.9800C47—C481.375 (6)
C10—C111.375 (3)C47—H470.9300
C10—C151.396 (3)C48—C491.392 (4)
C11—C121.382 (5)C48—H480.9300
C11—H110.9300C50—C511.493 (5)
C12—C131.355 (5)C50—H50A0.9700
C12—H120.9300C50—H50B0.9700
C13—C141.389 (5)C51—H51A0.9700
C13—H130.9300C51—H51B0.9700
C14—C151.390 (4)C52—C531.389 (4)
C14—H140.9300C52—C571.389 (3)
C16—C171.487 (4)C53—C541.363 (4)
C16—H16A0.9700C53—H530.9300
C16—H16B0.9700C54—C551.366 (4)
C17—H17A0.9700C54—H540.9300
C17—H17B0.9700C55—C561.387 (4)
C18—C191.387 (3)C55—H550.9300
C18—C231.393 (3)C56—C571.381 (3)
C19—C201.368 (4)C56—H560.9300
C19—H190.9300C57—C581.505 (3)
C20—C211.373 (4)C58—C591.565 (3)
C20—H200.9300C58—H580.9800
C21—C221.393 (4)C59—C601.538 (3)
C21—H210.9300C59—H590.9800
C22—C231.383 (3)C61—C661.369 (3)
C22—H220.9300C61—C621.374 (3)
C23—C241.506 (3)C62—C631.374 (3)
C24—C251.569 (3)C62—H620.9300
C24—H240.9800C63—C641.366 (4)
C25—C261.544 (3)C63—H630.9300
C25—H250.9800C64—C651.367 (3)
C27—C321.372 (3)C64—H640.9300
C27—C281.382 (3)C65—C661.391 (3)
C28—C291.380 (3)C65—H650.9300
C28—H280.9300C66—H660.9300
C29—C301.374 (4)C67—C681.522 (3)
C29—H290.9300C67—H67A0.9700
C30—C311.366 (3)C67—H67B0.9700
C30—H300.9300C68—H68A0.9700
C31—C321.382 (3)C68—H68B0.9700
C31—H310.9300O13—C701.319 (4)
C32—H320.9300O13—C711.464 (4)
C33—C341.524 (3)O14—C701.216 (4)
C33—H33A0.9700C69—C701.484 (5)
C33—H33B0.9700C69—H69A0.9600
C34—H34A0.9700C69—H69B0.9600
C34—H34B0.9700C69—H69C0.9600
O7—C601.216 (3)C71—C721.428 (6)
O8—C431.212 (3)C71—H71A0.9700
O9—C521.367 (3)C71—H71B0.9700
O9—C511.429 (3)C72—H72A0.9600
O10—C491.369 (4)C72—H72B0.9600
O10—C501.434 (4)C72—H72C0.9600
O11—C611.386 (2)
C18—O3—C17118.4 (2)C40—C35—O12124.3 (3)
C15—O4—C16120.3 (2)C36—C35—O12114.4 (3)
C27—O5—C25116.36 (16)C35—C36—C37117.3 (4)
C1—O6—C7116.40 (18)C35—C36—H36121.3
C9—N1—C34130.60 (19)C37—C36—H36121.3
C9—N1—C896.39 (16)C38—C37—C36122.3 (5)
C34—N1—C8132.96 (17)C38—C37—H37118.8
C26—N2—C33129.37 (19)C36—C37—H37118.8
C26—N2—C2496.51 (16)C39—C38—C37118.0 (5)
C33—N2—C24133.49 (17)C39—C38—H38121.0
C2—C1—C6121.0 (2)C37—C38—H38121.0
C2—C1—O6122.6 (2)C38—C39—C40122.2 (5)
C6—C1—O6116.4 (3)C38—C39—H39118.9
C1—C2—C3119.5 (3)C40—C39—H39118.9
C1—C2—H2120.3C35—C40—C39118.7 (4)
C3—C2—H2120.3C35—C40—H40120.6
C4—C3—C2120.3 (4)C39—C40—H40120.6
C4—C3—H3119.9O12—C41—C43116.36 (19)
C2—C3—H3119.9O12—C41—C42118.80 (19)
C3—C4—C5119.7 (3)C43—C41—C4285.36 (16)
C3—C4—H4120.1O12—C41—H41111.3
C5—C4—H4120.1C43—C41—H41111.3
C4—C5—C6121.4 (4)C42—C41—H41111.3
C4—C5—H5119.3N3—C42—C44115.9 (2)
C6—C5—H5119.3N3—C42—C4185.74 (16)
C1—C6—C5118.1 (3)C44—C42—C41115.83 (18)
C1—C6—H6121.0N3—C42—H42112.3
C5—C6—H6121.0C44—C42—H42112.3
O6—C7—C9119.80 (17)C41—C42—H42112.3
O6—C7—C8113.81 (18)O8—C43—N3132.2 (2)
C9—C7—C885.39 (15)O8—C43—C41136.1 (2)
O6—C7—H7111.8N3—C43—C4191.69 (17)
C9—C7—H7111.8C45—C44—C49118.2 (3)
C8—C7—H7111.8C45—C44—C42122.8 (3)
N1—C8—C10115.24 (18)C49—C44—C42119.0 (2)
N1—C8—C786.23 (15)C44—C45—C46120.8 (3)
C10—C8—C7116.93 (17)C44—C45—H45119.6
N1—C8—H8112.0C46—C45—H45119.6
C10—C8—H8112.0C47—C46—C45119.9 (4)
C7—C8—H8112.0C47—C46—H46120.0
O2—C9—N1131.5 (2)C45—C46—H46120.0
O2—C9—C7137.0 (2)C46—C47—C48120.6 (4)
N1—C9—C791.51 (17)C46—C47—H47119.7
C11—C10—C15118.2 (3)C48—C47—H47119.7
C11—C10—C8123.2 (2)C47—C48—C49119.5 (4)
C15—C10—C8118.6 (2)C47—C48—H48120.2
C10—C11—C12121.1 (3)C49—C48—H48120.2
C10—C11—H11119.5O10—C49—C44115.1 (2)
C12—C11—H11119.5O10—C49—C48123.9 (3)
C13—C12—C11120.2 (3)C44—C49—C48120.8 (3)
C13—C12—H12119.9O10—C50—C51106.7 (3)
C11—C12—H12119.9O10—C50—H50A110.4
C12—C13—C14121.1 (3)C51—C50—H50A110.4
C12—C13—H13119.5O10—C50—H50B110.4
C14—C13—H13119.5C51—C50—H50B110.4
C13—C14—C15118.3 (3)H50A—C50—H50B108.6
C13—C14—H14120.9O9—C51—C50106.1 (3)
C15—C14—H14120.9O9—C51—H51A110.5
O4—C15—C14123.7 (3)C50—C51—H51A110.5
O4—C15—C10114.9 (2)O9—C51—H51B110.5
C14—C15—C10121.2 (3)C50—C51—H51B110.5
O4—C16—C17106.5 (2)H51A—C51—H51B108.7
O4—C16—H16A110.4O9—C52—C53123.6 (2)
C17—C16—H16A110.4O9—C52—C57116.1 (2)
O4—C16—H16B110.4C53—C52—C57120.4 (3)
C17—C16—H16B110.4C54—C53—C52120.1 (3)
H16A—C16—H16B108.6C54—C53—H53120.0
O3—C17—C16106.4 (2)C52—C53—H53120.0
O3—C17—H17A110.4C53—C54—C55120.7 (3)
C16—C17—H17A110.4C53—C54—H54119.6
O3—C17—H17B110.4C55—C54—H54119.6
C16—C17—H17B110.4C54—C55—C56119.4 (3)
H17A—C17—H17B108.6C54—C55—H55120.3
O3—C18—C19122.8 (2)C56—C55—H55120.3
O3—C18—C23116.1 (2)C57—C56—C55121.3 (3)
C19—C18—C23121.0 (2)C57—C56—H56119.3
C20—C19—C18119.5 (3)C55—C56—H56119.4
C20—C19—H19120.2C56—C57—C52118.2 (2)
C18—C19—H19120.2C56—C57—C58121.3 (2)
C19—C20—C21121.1 (3)C52—C57—C58120.6 (2)
C19—C20—H20119.5N4—C58—C57114.02 (18)
C21—C20—H20119.5N4—C58—C5985.72 (15)
C20—C21—C22119.1 (3)C57—C58—C59115.33 (17)
C20—C21—H21120.4N4—C58—H58113.0
C22—C21—H21120.4C57—C58—H58113.0
C23—C22—C21121.2 (2)C59—C58—H58113.0
C23—C22—H22119.4O11—C59—C60120.8 (2)
C21—C22—H22119.4O11—C59—C58113.64 (17)
C22—C23—C18118.0 (2)C60—C59—C5885.43 (15)
C22—C23—C24121.6 (2)O11—C59—H59111.5
C18—C23—C24120.4 (2)C60—C59—H59111.5
N2—C24—C23114.57 (18)C58—C59—H59111.5
N2—C24—C2585.82 (15)O7—C60—N4132.2 (2)
C23—C24—C25116.63 (17)O7—C60—C59136.5 (2)
N2—C24—H24112.4N4—C60—C5991.30 (18)
C23—C24—H24112.4C66—C61—C62119.9 (2)
C25—C24—H24112.4C66—C61—O11123.28 (18)
O5—C25—C26119.82 (19)C62—C61—O11116.8 (2)
O5—C25—C24113.38 (17)C61—C62—C63119.7 (2)
C26—C25—C2485.41 (15)C61—C62—H62120.2
O5—C25—H25111.9C63—C62—H62120.2
C26—C25—H25111.9C64—C63—C62121.1 (2)
C24—C25—H25111.9C64—C63—H63119.4
O1—C26—N2132.0 (2)C62—C63—H63119.4
O1—C26—C25136.64 (19)C63—C64—C65119.3 (2)
N2—C26—C2591.35 (17)C63—C64—H64120.3
C32—C27—C28119.9 (2)C65—C64—H64120.3
C32—C27—O5123.30 (19)C64—C65—C66120.2 (2)
C28—C27—O5116.8 (2)C64—C65—H65119.9
C29—C28—C27119.5 (2)C66—C65—H65119.9
C29—C28—H28120.3C61—C66—C65119.8 (2)
C27—C28—H28120.3C61—C66—H66120.1
C30—C29—C28120.9 (2)C65—C66—H66120.1
C30—C29—H29119.6N4—C67—C68115.0 (2)
C28—C29—H29119.6N4—C67—H67A108.5
C31—C30—C29119.1 (2)C68—C67—H67A108.5
C31—C30—H30120.4N4—C67—H67B108.5
C29—C30—H30120.4C68—C67—H67B108.5
C30—C31—C32120.8 (2)H67A—C67—H67B107.5
C30—C31—H31119.6N3—C68—C67115.5 (2)
C32—C31—H31119.6N3—C68—H68A108.4
C27—C32—C31119.8 (2)C67—C68—H68A108.4
C27—C32—H32120.1N3—C68—H68B108.4
C31—C32—H32120.1C67—C68—H68B108.4
N2—C33—C34114.7 (2)H68A—C68—H68B107.5
N2—C33—H33A108.6C70—O13—C71115.7 (3)
C34—C33—H33A108.6C70—C69—H69A109.5
N2—C33—H33B108.6C70—C69—H69B109.5
C34—C33—H33B108.6H69A—C69—H69B109.5
H33A—C33—H33B107.6C70—C69—H69C109.5
N1—C34—C33114.73 (18)H69A—C69—H69C109.5
N1—C34—H34A108.6H69B—C69—H69C109.5
C33—C34—H34A108.6O14—C70—O13121.4 (4)
N1—C34—H34B108.6O14—C70—C69126.2 (4)
C33—C34—H34B108.6O13—C70—C69112.3 (3)
H34A—C34—H34B107.6C72—C71—O13106.2 (4)
C52—O9—C51118.7 (2)C72—C71—H71A110.5
C49—O10—C50118.9 (2)O13—C71—H71A110.5
C61—O11—C59116.70 (16)C72—C71—H71B110.5
C35—O12—C41117.5 (2)O13—C71—H71B110.5
C43—N3—C68130.9 (2)H71A—C71—H71B108.7
C43—N3—C4296.04 (17)C71—C72—H72A109.5
C68—N3—C42133.09 (18)C71—C72—H72B109.5
C60—N4—C67131.1 (2)H72A—C72—H72B109.5
C60—N4—C5896.23 (16)C71—C72—H72C109.5
C67—N4—C58132.03 (17)H72A—C72—H72C109.5
C40—C35—C36121.3 (3)H72B—C72—H72C109.5
C7—O6—C1—C239.0 (3)C40—C35—C36—C370.4 (5)
C7—O6—C1—C6143.2 (2)O12—C35—C36—C37179.8 (3)
C6—C1—C2—C30.5 (4)C35—C36—C37—C381.9 (7)
O6—C1—C2—C3178.2 (2)C36—C37—C38—C392.6 (9)
C1—C2—C3—C40.4 (5)C37—C38—C39—C401.0 (8)
C2—C3—C4—C51.4 (5)C36—C35—C40—C391.9 (5)
C3—C4—C5—C61.5 (6)O12—C35—C40—C39178.4 (3)
C2—C1—C6—C50.4 (4)C38—C39—C40—C351.2 (7)
O6—C1—C6—C5178.2 (3)C35—O12—C41—C43150.9 (2)
C4—C5—C6—C10.6 (5)C35—O12—C41—C42109.3 (2)
C1—O6—C7—C988.7 (2)C43—N3—C42—C44108.3 (2)
C1—O6—C7—C8172.60 (19)C68—N3—C42—C4471.3 (3)
C9—N1—C8—C10112.63 (19)C43—N3—C42—C418.43 (18)
C34—N1—C8—C1069.8 (3)C68—N3—C42—C41172.0 (3)
C9—N1—C8—C75.46 (17)O12—C41—C42—N3125.1 (2)
C34—N1—C8—C7172.1 (2)C43—C41—C42—N37.46 (16)
O6—C7—C8—N1125.40 (18)O12—C41—C42—C448.3 (3)
C9—C7—C8—N14.78 (15)C43—C41—C42—C44109.4 (2)
O6—C7—C8—C108.9 (3)C68—N3—C43—O86.5 (5)
C9—C7—C8—C10111.7 (2)C42—N3—C43—O8173.1 (3)
C34—N1—C9—O27.3 (4)C68—N3—C43—C41171.8 (2)
C8—N1—C9—O2175.1 (3)C42—N3—C43—C418.66 (18)
C34—N1—C9—C7172.1 (2)O12—C41—C43—O853.8 (4)
C8—N1—C9—C75.54 (18)C42—C41—C43—O8173.8 (3)
O6—C7—C9—O260.6 (4)O12—C41—C43—N3128.0 (2)
C8—C7—C9—O2175.5 (3)C42—C41—C43—N38.07 (17)
O6—C7—C9—N1120.1 (2)N3—C42—C44—C4515.0 (3)
C8—C7—C9—N15.19 (16)C41—C42—C44—C4583.2 (3)
N1—C8—C10—C1118.3 (3)N3—C42—C44—C49168.2 (2)
C7—C8—C10—C1180.8 (3)C41—C42—C44—C4993.5 (3)
N1—C8—C10—C15163.82 (19)C49—C44—C45—C460.9 (4)
C7—C8—C10—C1597.1 (2)C42—C44—C45—C46177.6 (2)
C15—C10—C11—C120.7 (4)C44—C45—C46—C472.0 (4)
C8—C10—C11—C12178.5 (3)C45—C46—C47—C483.3 (5)
C10—C11—C12—C131.0 (5)C46—C47—C48—C491.7 (5)
C11—C12—C13—C141.1 (6)C50—O10—C49—C44142.0 (3)
C12—C13—C14—C150.5 (5)C50—O10—C49—C4842.6 (4)
C16—O4—C15—C1432.2 (4)C45—C44—C49—O10173.0 (2)
C16—O4—C15—C10151.8 (2)C42—C44—C49—O103.9 (3)
C13—C14—C15—O4173.6 (3)C45—C44—C49—C482.5 (4)
C13—C14—C15—C102.2 (4)C42—C44—C49—C48179.4 (2)
C11—C10—C15—O4173.8 (2)C47—C48—C49—O10173.8 (3)
C8—C10—C15—O44.1 (3)C47—C48—C49—C441.3 (5)
C11—C10—C15—C142.3 (4)C49—O10—C50—C51130.4 (3)
C8—C10—C15—C14179.8 (2)C52—O9—C51—C50164.1 (2)
C15—O4—C16—C17134.4 (3)O10—C50—C51—O966.6 (3)
C18—O3—C17—C16153.4 (2)C51—O9—C52—C5315.0 (4)
O4—C16—C17—O368.4 (3)C51—O9—C52—C57164.8 (2)
C17—O3—C18—C1927.5 (3)O9—C52—C53—C54179.3 (2)
C17—O3—C18—C23154.7 (2)C57—C52—C53—C540.5 (4)
O3—C18—C19—C20177.7 (2)C52—C53—C54—C550.4 (4)
C23—C18—C19—C200.0 (3)C53—C54—C55—C560.4 (4)
C18—C19—C20—C210.2 (3)C54—C55—C56—C570.6 (4)
C19—C20—C21—C220.2 (4)C55—C56—C57—C520.7 (3)
C20—C21—C22—C230.1 (3)C55—C56—C57—C58177.1 (2)
C21—C22—C23—C180.2 (3)O9—C52—C57—C56179.2 (2)
C21—C22—C23—C24179.76 (19)C53—C52—C57—C560.6 (3)
O3—C18—C23—C22177.61 (18)O9—C52—C57—C583.0 (3)
C19—C18—C23—C220.2 (3)C53—C52—C57—C58177.2 (2)
O3—C18—C23—C242.4 (3)C60—N4—C58—C57106.8 (2)
C19—C18—C23—C24179.81 (18)C67—N4—C58—C5764.9 (3)
C26—N2—C24—C23109.9 (2)C60—N4—C58—C599.08 (18)
C33—N2—C24—C2361.3 (3)C67—N4—C58—C59179.2 (2)
C26—N2—C24—C257.52 (18)C56—C57—C58—N436.9 (3)
C33—N2—C24—C25178.7 (2)C52—C57—C58—N4145.29 (19)
C22—C23—C24—N232.3 (3)C56—C57—C58—C5960.0 (3)
C18—C23—C24—N2147.69 (18)C52—C57—C58—C59117.8 (2)
C22—C23—C24—C2565.7 (3)C61—O11—C59—C6089.5 (2)
C18—C23—C24—C25114.3 (2)C61—O11—C59—C58171.27 (19)
C27—O5—C25—C2685.4 (2)N4—C58—C59—O11129.7 (2)
C27—O5—C25—C24176.11 (19)C57—C58—C59—O1115.1 (3)
N2—C24—C25—O5127.13 (19)N4—C58—C59—C607.93 (16)
C23—C24—C25—O511.7 (3)C57—C58—C59—C60106.7 (2)
N2—C24—C25—C266.54 (16)C67—N4—C60—O71.0 (5)
C23—C24—C25—C26108.9 (2)C58—N4—C60—O7170.9 (3)
C33—N2—C26—O11.5 (4)C67—N4—C60—C59178.9 (2)
C24—N2—C26—O1173.3 (3)C58—N4—C60—C599.21 (18)
C33—N2—C26—C25179.4 (2)O11—C59—C60—O756.5 (4)
C24—N2—C26—C257.62 (18)C58—C59—C60—O7171.4 (3)
O5—C25—C26—O159.4 (4)O11—C59—C60—N4123.5 (2)
C24—C25—C26—O1173.8 (3)C58—C59—C60—N48.66 (17)
O5—C25—C26—N2121.5 (2)C59—O11—C61—C6640.3 (3)
C24—C25—C26—N27.15 (17)C59—O11—C61—C62142.4 (2)
C25—O5—C27—C3242.8 (3)C66—C61—C62—C630.1 (4)
C25—O5—C27—C28139.8 (2)O11—C61—C62—C63177.4 (3)
C32—C27—C28—C290.5 (4)C61—C62—C63—C640.1 (5)
O5—C27—C28—C29178.0 (3)C62—C63—C64—C650.0 (5)
C27—C28—C29—C300.2 (5)C63—C64—C65—C660.2 (4)
C28—C29—C30—C310.8 (4)C62—C61—C66—C650.1 (4)
C29—C30—C31—C320.7 (4)O11—C61—C66—C65177.0 (2)
C28—C27—C32—C310.6 (4)C64—C65—C66—C610.3 (4)
O5—C27—C32—C31177.9 (2)C60—N4—C67—C68112.9 (3)
C30—C31—C32—C270.0 (4)C58—N4—C67—C6878.0 (3)
C26—N2—C33—C34107.1 (3)C43—N3—C68—C67112.1 (3)
C24—N2—C33—C3484.2 (3)C42—N3—C68—C6768.5 (4)
C9—N1—C34—C33112.5 (3)N4—C67—C68—N397.4 (3)
C8—N1—C34—C3364.3 (3)C71—O13—C70—O142.0 (5)
N2—C33—C34—N195.2 (2)C71—O13—C70—C69174.3 (4)
C41—O12—C35—C4017.9 (4)C70—O13—C71—C72175.5 (4)
C41—O12—C35—C36162.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C53—H53···O60.932.523.344 (3)147
C2—H2···O20.932.423.250 (3)149
C32—H32···O10.932.333.178 (3)151
C66—H66···O70.932.483.299 (3)147

Experimental details

Crystal data
Chemical formulaC34H30N2O6·0.5(C4H8O2)
Mr606.65
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)18.037 (3), 17.201 (3), 21.589 (4)
β (°) 108.722 (10)
V3)6343.67 (19)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.18 × 0.16 × 0.13
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.984, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections
64493, 13208, 7192
Rint0.046
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.175, 1.02
No. of reflections13208
No. of parameters813
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.24

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C53—H53···O60.932.523.344 (3)147
C2—H2···O20.932.423.250 (3)149
C32—H32···O10.932.333.178 (3)151
C66—H66···O70.932.483.299 (3)147
 

Acknowledgements

NA, AIA and UK extend their appreciation to the Deanship of Scientific Research at King Saud University for their funding of this work through the research grant No. RGP-VPP-026.

References

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First citationBruker (1998). SADABS. Bruker AXS Inc., Maddison, Wisconsin, USA.  Google Scholar
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First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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First citationVaccaro, W. D., Sher, R. & Davis, H. R. Jr (1998). Bioorg. Med. Chem. Lett. 8, 35–40.  Web of Science CrossRef CAS PubMed Google Scholar

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