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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 2| February 2013| Pages o297-o298

9-(3,4-Dimeth­­oxy­phen­yl)-3,3,6,6-tetra­methyl-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bDepartment of Chemistry, Shivaji University, Kolhapur, 416 004 (MS), India
*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 8 January 2013; accepted 23 January 2013; online 26 January 2013)

The asymmetric unit of the title compound, C25H31NO4, contains two independent mol­ecules. In one mol­ecule, the benzene ring and an attached meth­oxy group were refined as disordered over two sets of sites in a 0.65 (4): 0.35 (4) ratio. In both mol­ecules, the central ring of the acridinedione system adopts a flattened boat conformation. The four essentially planar atoms of this ring [maximum deviations = 0.006 (5) Å in both mol­ecules] forms dihedral angles of 86.8 (2) and 87.6 (2)°, respectively, with the major and minor components in the disordered benzene ring and 87.3 (2)° with the benzene ring in the fully ordered mol­ecule. The two outer rings of the acridinedione system adopt sofa conformations in both mol­ecules. In the crystal, N—H⋯O hydrogen bonds form two independent chains along [100]. C—H⋯O hydrogen bonds link the chains, forming a three-dimensional network.

Related literature

For applications of acridines, see: Murugan et al. (1998[Murugan, P., Shanmugasundaram, P., Ramakrishnan, V. T., Venkatachalapathy, B., Srividya, N., Ramamurthy, P., Gunasekaran, K. & Velmurugan, D. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 999-1003.]); Leon et al. (2008[Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.]); Josephrajan et al. (2005[Josephrajan, T., Ramakrishnan, V. T., Kathiravan, G. & Muthumary, J. (2005). ARKIVOC, pp. 124-136.]); Srividya et al. (1998[Srividya, N., Ramamurthy, P. & Ramakrishnan, V. T. (1998). Spectrochim. Acta Part A, 54, 245-253.], 1996[Srividya, N., Ramamurthy, P., Shanmugasundaram, P. & Ramakrishnan, V. T. (1996). J. Org. Chem. 61, 5083-5089.]). For related structures, see: Balamurugan et al. (2009[Balamurugan, P., Jagan, R., Thiagarajan, V. M., Yamin, B. & Sivakumar, K. (2009). Acta Cryst. E65, o271.]); Zhao & Teng (2008[Zhao, L.-L. & Teng, D. (2008). Acta Cryst. E64, o1772-o1773.]); Kant et al. (2013a[Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Patil, P. P. & Deshmukh, M. B. (2013a). Acta Cryst. E69, o100.],b[Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Jagadale, S. D. & Deshmukh, M. B. (2013b). Acta Cryst. E69, o101.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C25H31NO4

  • Mr = 409.51

  • Orthorhombic, P c a 21

  • a = 14.1607 (6) Å

  • b = 15.3126 (10) Å

  • c = 21.1196 (14) Å

  • V = 4579.5 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.672, Tmax = 1.000

  • 14639 measured reflections

  • 6386 independent reflections

  • 4075 reflections with I > 2σ(I)

  • Rint = 0.055

Refinement
  • R[F2 > 2σ(F2)] = 0.059

  • wR(F2) = 0.127

  • S = 1.01

  • 6386 reflections

  • 604 parameters

  • 53 restraints

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N12A—H12A⋯O1Ai 0.86 2.07 2.846 (4) 150
N12B—H12B⋯O8Bii 0.86 2.05 2.885 (4) 165
C2A—H2AA⋯O1Bii 0.97 2.45 3.400 (6) 166
C16A—H16D⋯O25Aiii 0.96 2.61 3.477 (12) 150
C7A—H7AB⋯O27Biv 0.97 2.47 3.432 (6) 169
C7B—H7BB⋯O8Ai 0.97 2.57 3.507 (5) 162
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+1, z]; (ii) [x+{\script{1\over 2}}, -y, z]; (iii) [-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]; (iv) [-x, -y+1, z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

The 1,4- dihydropyridine (DHP) nucleus act as a versatile intermediate for the synthesis of several pharmaceuticals together with those of cardiovascular drugs and as a calcium channel modulators, laser dyes and photo initiators (Leon et al., 2008). Acridines, the earliest known antibiotics and are toxic towards bacteria. Some acridinedione derivatives show good inhibition against the pathogen Vibrio isolate-I (Josephrajan et al., 2005). Certain acridine-1,8-diones exhibit fluorescence activities (Murugan et al., 1998) and a few acridinedione derivatives also show photophysical (Srividya et al., 1998) and electrochemical properties (Srividya et al., 1996). Thus, the accurate description of crystal structures of substituted acridinediones are expected to provide useful information on the role of substituents in influencing molecular conformation which has a direct relationship to biological activity. This paper deals with the crystal structure of a 3,4-dimethoxyphenyl substituted tetramethyl acridinedione, (I).

The asymmetric unit of the title compound comprises of two crystallographically independent molecules, A and B (Fig.1). In molecule A, the benzene ring and one attached methoxy group is disordered over two sets of sites in a 0.65 (4):0.35 (4) ratio. Bond lengths and angles are normal and correspond to those observed in related structures (Balamurugan et al., 2009; Zhao & Teng 2008; Kant et al. (2013a,b)). The central ring (C9/C10/C11/N12/C13/C14) of the acridinedione moiety adopts a flattened boat conformation (ΔCs(C9A) = 1.32 & ΔCs (C13A—C14A) = 10.43; ΔCs(C9B) = 1.34 & ΔCs (C13B—C14B) = 12.58) and the four essentially planar atoms (C10/C11/C13/C14) of this ring (maximum deviation-0.006 (5) Å for C11A and -0.006 (5) Å for C13B) forms a dihedral angle of 86.8 (2)° and 87.6 (2)° with the major and minor components of disorder benzene ring in molecule A and 87.3 (2)° with the benzene ring in molecule B. Both the outer rings adopt sofa conformations (ΔCs (C3A) = 7.99; ΔCs (C6A) = 4.61; ΔCs (C3B) = 8.34; ΔCs (C6B) = 8.93) (Duax & Norton, 1975). In the crystal N—H···O hydrogen bonds (Table 1) form two independent one-dimensional chains parallel to [100]. In addition weak C—H···O hydrogen bonds link chains to form a three-dimensional network (Fig. 2).

Related literature top

For applications of acridines, see: Murugan et al. (1998); Leon et al. (2008); Josephrajan et al. (2005); Srividya et al. (1998, 1996). For related structures, see: Balamurugan et al. (2009); Zhao & Teng (2008); Kant et al. (2013a,b). For ring conformations, see: Duax & Norton (1975).

Experimental top

In a 50 ml round bottom flask, a mixture of dimedone (2 mmole), 3,4 - dimethoxy benzaldehyde 2(1 mmole) and ammonium acetate (1.2 mmole) in aqu. ethanol (7 ml) was stirred at room temperature for 5 min. To this [CMIM][HSO4](3-carboxymethyl-1-methylimidazolium bisulfate)(20 mol %) was added and the reaction mixture heated at 348–351 K for 1.5 hrs. The progress of reaction was monitored by TLC. After completion of reaction, the mixture was gradually cooled to RT and poured on ice water under stirring. A precipitate was formed which was filtered and dried. The crude product was recrystallized from ethanol.

M.P.: 559–563 K, Yield:78%. IR(KBr): 3273, 3200, 3071, 2954, 1642, 1610 cm-1. 1H NMR(300 MHz, DMSO-d6): δ = 7.9 (s, 1H, NH); 7.2–6.2 (m, 3H, Ar—H); 5.0 (s, 1H, CH); 3.8 (s, 3H, OCH3); 3.7 (s, 3H, OCH3); 2.3–2.1 (m, 8H, CH2); 1.0 (s, 6H, CH3); 0.9 (s,6H, CH3).

Refinement top

All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with N—H distances of 0.86 Å, C—H distances of 0.93–0.98 Å and with Uiso(H) = 1.2Ueq(C/N) or 1.5Ueq(methyl C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. Atoms labeled with 'C' are the minor component of disorder.
[Figure 2] Fig. 2. The packing arrangement of molecules viewed along the b axis. The dashed lines show intermolecular C—H···O and N—H···O hydrogen bonds. Only H atoms involved in hydrogen bonds are shown. The disorder is not shown.
9-(3,4-Dimethoxyphenyl)-3,3,6,6-tetramethyl-1,2,3,4,5,6,7,8,9,10-decahydroacridine-1,8-dione top
Crystal data top
C25H31NO4F(000) = 1760
Mr = 409.51Dx = 1.188 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 6069 reflections
a = 14.1607 (6) Åθ = 3.5–29.0°
b = 15.3126 (10) ŵ = 0.08 mm1
c = 21.1196 (14) ÅT = 293 K
V = 4579.5 (5) Å3Block, yellow
Z = 80.3 × 0.2 × 0.2 mm
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
6386 independent reflections
Radiation source: fine-focus sealed tube4075 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
Detector resolution: 16.1049 pixels mm-1θmax = 25.0°, θmin = 3.5°
ω scansh = 1616
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 1813
Tmin = 0.672, Tmax = 1.000l = 2521
14639 measured reflections
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0377P)2]
where P = (Fo2 + 2Fc2)/3
6386 reflections(Δ/σ)max = 0.002
604 parametersΔρmax = 0.17 e Å3
53 restraintsΔρmin = 0.17 e Å3
Crystal data top
C25H31NO4V = 4579.5 (5) Å3
Mr = 409.51Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 14.1607 (6) ŵ = 0.08 mm1
b = 15.3126 (10) ÅT = 293 K
c = 21.1196 (14) Å0.3 × 0.2 × 0.2 mm
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
6386 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
4075 reflections with I > 2σ(I)
Tmin = 0.672, Tmax = 1.000Rint = 0.055
14639 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05953 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.01Δρmax = 0.17 e Å3
6386 reflectionsΔρmin = 0.17 e Å3
604 parameters
Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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*/UeqOcc. (<1)
O1A0.41575 (18)0.5230 (2)0.62071 (19)0.0548 (9)
O8A0.26645 (19)0.7813 (2)0.73491 (19)0.0666 (10)
O27A0.4145 (2)0.4704 (2)0.92959 (18)0.0681 (10)
N12A0.0923 (2)0.5381 (2)0.6676 (2)0.0474 (10)
H12A0.03880.51150.66740.057*
C1A0.3348 (3)0.4965 (3)0.6129 (3)0.0428 (12)
C2A0.3141 (3)0.4280 (3)0.5643 (3)0.0550 (13)
H2AA0.37020.39270.55820.066*
H2AB0.30000.45650.52440.066*
C3A0.2315 (3)0.3681 (3)0.5818 (2)0.0458 (11)
C4A0.1465 (2)0.4260 (3)0.5952 (2)0.0448 (11)
H4AA0.12280.44910.55550.054*
H4AB0.09690.39090.61400.054*
C5A0.0075 (3)0.6611 (3)0.7126 (2)0.0445 (11)
H5AA0.03690.61730.72720.053*
H5AB0.01820.68740.67450.053*
C6A0.0183 (3)0.7312 (3)0.7634 (2)0.0412 (10)
C7A0.0994 (3)0.7905 (3)0.7444 (2)0.0465 (12)
H7AA0.08100.82320.70710.056*
H7AB0.11040.83220.77820.056*
C8A0.1907 (3)0.7431 (3)0.7306 (2)0.0439 (11)
C9A0.2752 (2)0.6035 (3)0.6965 (2)0.0407 (11)
H9AA0.32210.64360.67860.049*
C10A0.2565 (2)0.5319 (3)0.6482 (2)0.0369 (10)
C11A0.1688 (3)0.5000 (3)0.6383 (2)0.0351 (11)
C13A0.0997 (2)0.6177 (3)0.6969 (2)0.0382 (10)
C14A0.1847 (2)0.6543 (3)0.7080 (2)0.0365 (10)
C15A0.2574 (3)0.3134 (3)0.6400 (3)0.0685 (16)
H15D0.20330.28050.65340.103*
H15E0.27730.35140.67360.103*
H15F0.30780.27420.62940.103*
C16A0.2084 (3)0.3074 (3)0.5267 (3)0.0715 (16)
H16D0.19200.34160.49020.107*
H16E0.15620.27060.53800.107*
H16F0.26250.27190.51720.107*
C17A0.0379 (3)0.6895 (3)0.8280 (2)0.0603 (13)
H17D0.09080.65060.82450.090*
H17E0.01670.65740.84150.090*
H17F0.05190.73440.85830.090*
C18A0.0729 (3)0.7854 (3)0.7663 (3)0.0587 (13)
H18D0.08660.80840.72500.088*
H18E0.06490.83270.79560.088*
H18F0.12410.74900.77990.088*
C19A0.3146 (3)0.5673 (3)0.7580 (2)0.0402 (10)
C22A0.3848 (3)0.5054 (3)0.8740 (2)0.0494 (12)
O25A0.2757 (9)0.3913 (8)0.8741 (5)0.074 (4)0.65 (4)
C20A0.2766 (6)0.4936 (5)0.7872 (3)0.043 (3)0.65 (4)
H20B0.22690.46440.76760.052*0.65 (4)
C21A0.3099 (6)0.4630 (5)0.8431 (3)0.045 (2)0.65 (4)
C23A0.4224 (6)0.5783 (6)0.8451 (4)0.065 (4)0.65 (4)
H23B0.47210.60750.86470.078*0.65 (4)
C24A0.3881 (6)0.6096 (6)0.7876 (4)0.055 (3)0.65 (4)
H24B0.41480.65890.76920.066*0.65 (4)
C26A0.2016 (14)0.3452 (12)0.8480 (7)0.078 (6)0.65 (4)
H26D0.17770.30440.87860.117*0.65 (4)
H26E0.22310.31410.81130.117*0.65 (4)
H26F0.15230.38490.83610.117*0.65 (4)
O25C0.2505 (17)0.420 (3)0.8889 (11)0.092 (9)0.35 (4)
C20C0.2630 (12)0.5092 (18)0.7952 (8)0.043 (4)0.35 (4)
H20C0.20460.48980.78080.052*0.35 (4)
C21C0.2953 (12)0.4801 (19)0.8519 (8)0.056 (5)0.35 (4)
C23C0.4336 (12)0.5662 (16)0.8386 (9)0.062 (5)0.35 (4)
H23C0.48910.58980.85490.075*0.35 (4)
C24C0.4021 (14)0.593 (2)0.7793 (10)0.055 (3)0.35 (4)
H24C0.44010.62860.75410.066*0.35 (4)
C26C0.184 (3)0.365 (3)0.8620 (15)0.081 (14)0.35 (4)
H26G0.15870.32720.89390.122*0.35 (4)
H26H0.21370.33070.82950.122*0.35 (4)
H26I0.13440.39930.84380.122*0.35 (4)
C28A0.5051 (4)0.4963 (4)0.9522 (3)0.0720 (18)
H28D0.52000.46420.98990.108*
H28E0.50450.55770.96150.108*
H28F0.55180.48460.92040.108*
O1B0.0121 (2)0.2853 (2)0.5241 (2)0.0810 (12)
O8B0.16622 (19)0.0344 (2)0.6456 (2)0.0734 (12)
O25B0.0012 (2)0.1058 (2)0.40468 (18)0.0766 (11)
O27B0.1489 (2)0.0429 (2)0.34795 (17)0.0604 (9)
N12B0.1604 (2)0.0524 (2)0.61100 (19)0.0458 (10)
H12B0.21410.02650.61400.055*
C1B0.0648 (3)0.2511 (3)0.5358 (3)0.0541 (13)
C2B0.1562 (3)0.2996 (3)0.5243 (3)0.0589 (14)
H2BA0.14720.33980.48930.071*
H2BB0.17100.33400.56160.071*
C3B0.2397 (3)0.2402 (3)0.5095 (2)0.0506 (12)
C4B0.2483 (3)0.1713 (3)0.5617 (2)0.0502 (12)
H4BA0.27420.19830.59950.060*
H4BB0.29200.12630.54810.060*
C5B0.1020 (3)0.0532 (3)0.6868 (3)0.0531 (13)
H5BA0.15360.08920.67140.064*
H5BB0.12280.02580.72580.064*
C6B0.0174 (3)0.1123 (3)0.7014 (3)0.0533 (13)
C7B0.0673 (3)0.0519 (3)0.7119 (3)0.0622 (14)
H7BA0.05740.01930.75070.075*
H7BB0.12330.08750.71770.075*
C8B0.0852 (3)0.0110 (3)0.6595 (3)0.0491 (14)
C9B0.0208 (2)0.1138 (3)0.5758 (2)0.0424 (11)
H9BA0.06830.15500.59130.051*
C10B0.0698 (3)0.1646 (3)0.5638 (2)0.0401 (11)
C11B0.1546 (3)0.1297 (3)0.5778 (2)0.0399 (10)
C13B0.0824 (3)0.0154 (3)0.6397 (3)0.0407 (11)
C14B0.0046 (2)0.0469 (3)0.6264 (2)0.0406 (11)
C15B0.2225 (4)0.1969 (4)0.4448 (3)0.0794 (17)
H15A0.21900.24110.41270.119*
H15B0.27340.15770.43550.119*
H15C0.16410.16500.44600.119*
C16B0.3307 (3)0.2941 (4)0.5059 (3)0.0820 (19)
H16A0.34470.31800.54680.123*
H16B0.38180.25730.49250.123*
H16C0.32260.34080.47600.123*
C17B0.0042 (3)0.1733 (3)0.6459 (3)0.0672 (15)
H17A0.06080.20550.65470.101*
H17B0.01270.13940.60810.101*
H17C0.04750.21310.64010.101*
C18B0.0376 (4)0.1652 (4)0.7612 (3)0.0847 (19)
H18A0.01620.20090.77110.127*
H18B0.09170.20180.75440.127*
H18C0.04990.12620.79590.127*
C19B0.0573 (3)0.0748 (3)0.5145 (2)0.0448 (12)
C20B0.0120 (3)0.0035 (3)0.4882 (2)0.0424 (12)
H20A0.04060.01950.50870.051*
C21B0.0421 (3)0.0343 (3)0.4328 (2)0.0466 (11)
C22B0.1219 (3)0.0023 (3)0.4027 (3)0.0522 (14)
C23B0.1665 (3)0.0674 (4)0.4282 (3)0.083 (2)
H23A0.21910.09060.40790.100*
C24B0.1351 (3)0.1051 (4)0.4845 (3)0.0768 (18)
H24A0.16820.15180.50170.092*
C26B0.0708 (3)0.1487 (4)0.4394 (3)0.0827 (19)
H26A0.09270.19840.41590.124*
H26B0.12240.10910.44630.124*
H26C0.04610.16760.47940.124*
C28B0.2427 (3)0.0244 (3)0.3247 (3)0.0665 (15)
H28A0.25570.06050.28870.100*
H28B0.28800.03620.35740.100*
H28C0.24660.03600.31270.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0224 (15)0.062 (2)0.080 (3)0.0021 (15)0.0027 (15)0.0113 (19)
O8A0.0491 (19)0.047 (2)0.103 (3)0.0204 (15)0.0055 (18)0.010 (2)
O27A0.056 (2)0.093 (3)0.056 (2)0.0114 (19)0.0208 (18)0.008 (2)
N12A0.0218 (16)0.045 (2)0.076 (3)0.0030 (15)0.0028 (17)0.020 (2)
C1A0.035 (3)0.038 (3)0.055 (3)0.0047 (18)0.001 (2)0.008 (2)
C2A0.040 (3)0.055 (3)0.071 (4)0.005 (2)0.012 (2)0.005 (3)
C3A0.042 (2)0.043 (2)0.052 (3)0.010 (2)0.003 (2)0.005 (2)
C4A0.030 (2)0.046 (3)0.059 (3)0.0029 (19)0.005 (2)0.013 (2)
C5A0.036 (2)0.047 (3)0.050 (3)0.0037 (19)0.002 (2)0.015 (2)
C6A0.041 (2)0.039 (3)0.043 (3)0.0016 (19)0.001 (2)0.003 (2)
C7A0.049 (3)0.037 (2)0.054 (3)0.001 (2)0.002 (2)0.004 (2)
C8A0.046 (3)0.042 (3)0.043 (3)0.008 (2)0.003 (2)0.004 (2)
C9A0.024 (2)0.037 (2)0.061 (3)0.0044 (17)0.0048 (19)0.003 (2)
C10A0.023 (2)0.034 (2)0.054 (3)0.0009 (18)0.0026 (18)0.002 (2)
C11A0.032 (2)0.040 (2)0.034 (3)0.0054 (16)0.0045 (19)0.005 (2)
C13A0.028 (2)0.041 (2)0.046 (3)0.0004 (17)0.0014 (18)0.005 (2)
C14A0.028 (2)0.036 (2)0.045 (3)0.0037 (17)0.0025 (18)0.008 (2)
C15A0.056 (3)0.053 (3)0.096 (4)0.001 (3)0.010 (3)0.021 (3)
C16A0.072 (4)0.058 (4)0.084 (4)0.017 (3)0.003 (3)0.021 (3)
C17A0.068 (3)0.060 (3)0.052 (3)0.005 (3)0.002 (2)0.004 (3)
C18A0.055 (3)0.052 (3)0.070 (3)0.015 (2)0.003 (3)0.017 (3)
C19A0.029 (2)0.039 (2)0.053 (3)0.0024 (16)0.0120 (18)0.004 (2)
C22A0.037 (2)0.062 (3)0.050 (3)0.0014 (18)0.011 (2)0.000 (2)
O25A0.068 (5)0.093 (6)0.060 (5)0.036 (5)0.011 (4)0.020 (4)
C20A0.033 (4)0.051 (6)0.046 (5)0.016 (4)0.004 (3)0.010 (3)
C21A0.033 (4)0.056 (5)0.046 (4)0.006 (3)0.007 (3)0.001 (3)
C23A0.050 (7)0.063 (7)0.081 (7)0.012 (5)0.036 (6)0.008 (6)
C24A0.041 (3)0.046 (5)0.078 (4)0.012 (3)0.027 (3)0.011 (4)
C26A0.055 (9)0.071 (8)0.108 (13)0.016 (6)0.005 (7)0.005 (8)
C19C0.029 (2)0.039 (2)0.053 (3)0.0024 (16)0.0120 (18)0.004 (2)
C22C0.037 (2)0.062 (3)0.050 (3)0.0014 (18)0.011 (2)0.000 (2)
O25C0.093 (11)0.127 (17)0.056 (9)0.057 (12)0.011 (9)0.028 (11)
C20C0.027 (7)0.046 (10)0.056 (9)0.004 (6)0.010 (5)0.006 (7)
C21C0.048 (8)0.080 (13)0.039 (9)0.022 (8)0.010 (6)0.004 (7)
C23C0.029 (9)0.077 (15)0.081 (12)0.003 (7)0.022 (7)0.020 (10)
C24C0.041 (3)0.046 (5)0.078 (4)0.012 (3)0.027 (3)0.011 (4)
C26C0.054 (15)0.11 (3)0.083 (17)0.05 (2)0.001 (15)0.02 (2)
C28A0.048 (3)0.103 (5)0.066 (4)0.004 (3)0.030 (3)0.005 (3)
O1B0.063 (2)0.050 (2)0.130 (4)0.0236 (19)0.002 (2)0.003 (2)
O8B0.0238 (16)0.066 (2)0.131 (4)0.0006 (16)0.0040 (18)0.018 (2)
O25B0.080 (2)0.080 (3)0.070 (3)0.046 (2)0.0272 (19)0.031 (2)
O27B0.0521 (19)0.074 (2)0.055 (2)0.0110 (17)0.0196 (16)0.0152 (19)
N12B0.0212 (17)0.054 (2)0.062 (3)0.0031 (16)0.0006 (16)0.004 (2)
C1B0.060 (3)0.043 (3)0.059 (3)0.013 (2)0.002 (2)0.007 (3)
C2B0.060 (3)0.044 (3)0.072 (4)0.008 (2)0.008 (3)0.007 (3)
C3B0.047 (3)0.052 (3)0.053 (3)0.001 (2)0.009 (2)0.005 (3)
C4B0.037 (2)0.055 (3)0.058 (3)0.004 (2)0.010 (2)0.005 (3)
C5B0.039 (2)0.062 (3)0.058 (3)0.010 (2)0.006 (2)0.006 (3)
C6B0.036 (2)0.058 (3)0.066 (4)0.010 (2)0.004 (2)0.001 (3)
C7B0.049 (3)0.055 (3)0.082 (4)0.013 (2)0.017 (3)0.012 (3)
C8B0.028 (3)0.050 (3)0.069 (4)0.006 (2)0.004 (2)0.021 (3)
C9B0.025 (2)0.038 (2)0.064 (3)0.0089 (18)0.001 (2)0.017 (2)
C10B0.032 (2)0.042 (3)0.047 (3)0.0053 (18)0.0007 (19)0.013 (2)
C11B0.035 (2)0.040 (2)0.044 (3)0.0010 (19)0.0000 (19)0.000 (2)
C13B0.026 (2)0.043 (3)0.054 (3)0.0071 (18)0.001 (2)0.005 (2)
C14B0.024 (2)0.042 (3)0.056 (3)0.0056 (18)0.001 (2)0.014 (2)
C15B0.098 (4)0.079 (4)0.061 (4)0.008 (3)0.018 (3)0.012 (3)
C16B0.063 (3)0.084 (5)0.100 (5)0.020 (3)0.021 (3)0.008 (4)
C17B0.052 (3)0.048 (3)0.102 (4)0.002 (2)0.001 (3)0.018 (3)
C18B0.083 (4)0.082 (5)0.089 (4)0.019 (3)0.002 (3)0.031 (4)
C19B0.030 (2)0.042 (3)0.062 (3)0.0089 (19)0.005 (2)0.012 (2)
C20B0.033 (2)0.047 (3)0.048 (3)0.0096 (18)0.012 (2)0.012 (2)
C21B0.041 (2)0.049 (3)0.050 (3)0.011 (2)0.006 (2)0.010 (3)
C22B0.050 (3)0.056 (3)0.051 (3)0.010 (2)0.019 (3)0.009 (3)
C23B0.065 (3)0.088 (4)0.097 (5)0.039 (3)0.048 (3)0.036 (4)
C24B0.066 (3)0.072 (4)0.093 (4)0.039 (3)0.037 (3)0.044 (3)
C26B0.070 (3)0.087 (4)0.091 (4)0.054 (3)0.029 (3)0.035 (4)
C28B0.052 (3)0.086 (4)0.062 (4)0.004 (3)0.021 (3)0.006 (3)
Geometric parameters (Å, º) top
O1A—C1A1.227 (5)C26C—H26H0.9600
O8A—C8A1.225 (4)C26C—H26I0.9600
O27A—C22A1.357 (6)C28A—H28D0.9600
O27A—C28A1.425 (5)C28A—H28E0.9600
N12A—C13A1.372 (5)C28A—H28F0.9600
N12A—C11A1.377 (5)O1B—C1B1.233 (5)
N12A—H12A0.8600O8B—C8B1.238 (5)
C1A—C10A1.441 (6)O25B—C21B1.373 (5)
C1A—C2A1.497 (7)O25B—C26B1.417 (5)
C2A—C3A1.532 (6)O27B—C22B1.368 (6)
C2A—H2AA0.9700O27B—C28B1.443 (5)
C2A—H2AB0.9700N12B—C11B1.378 (5)
C3A—C4A1.523 (5)N12B—C13B1.382 (5)
C3A—C16A1.525 (6)N12B—H12B0.8600
C3A—C15A1.531 (6)C1B—C10B1.453 (6)
C4A—C11A1.487 (6)C1B—C2B1.511 (6)
C4A—H4AA0.9700C2B—C3B1.525 (6)
C4A—H4AB0.9700C2B—H2BA0.9700
C5A—C13A1.501 (5)C2B—H2BB0.9700
C5A—C6A1.527 (5)C3B—C4B1.532 (6)
C5A—H5AA0.9700C3B—C16B1.532 (6)
C5A—H5AB0.9700C3B—C15B1.537 (6)
C6A—C7A1.518 (6)C4B—C11B1.510 (5)
C6A—C17A1.530 (6)C4B—H4BA0.9700
C6A—C18A1.536 (5)C4B—H4BB0.9700
C7A—C8A1.512 (6)C5B—C13B1.474 (6)
C7A—H7AA0.9700C5B—C6B1.533 (5)
C7A—H7AB0.9700C5B—H5BA0.9700
C8A—C14A1.444 (5)C5B—H5BB0.9700
C9A—C19A1.518 (5)C6B—C18B1.528 (7)
C9A—C14A1.519 (5)C6B—C17B1.530 (6)
C9A—C10A1.520 (6)C6B—C7B1.531 (6)
C9A—H9AA0.9800C7B—C8B1.489 (7)
C10A—C11A1.351 (5)C7B—H7BA0.9700
C13A—C14A1.348 (5)C7B—H7BB0.9700
C15A—H15D0.9600C8B—C14B1.446 (6)
C15A—H15E0.9600C9B—C14B1.499 (6)
C15A—H15F0.9600C9B—C19B1.516 (6)
C16A—H16D0.9600C9B—C10B1.520 (5)
C16A—H16E0.9600C9B—H9BA0.9800
C16A—H16F0.9600C10B—C11B1.348 (5)
C17A—H17D0.9600C13B—C14B1.352 (5)
C17A—H17E0.9600C15B—H15A0.9600
C17A—H17F0.9600C15B—H15B0.9600
C18A—H18D0.9600C15B—H15C0.9600
C18A—H18E0.9600C16B—H16A0.9600
C18A—H18F0.9600C16B—H16B0.9600
C19A—C24A1.376 (5)C16B—H16C0.9600
C19A—C20A1.394 (7)C17B—H17A0.9600
C22A—C23A1.379 (7)C17B—H17B0.9600
C22A—C21A1.404 (7)C17B—H17C0.9600
O25A—C21A1.366 (7)C18B—H18A0.9600
O25A—C26A1.380 (7)C18B—H18B0.9600
C20A—C21A1.356 (8)C18B—H18C0.9600
C20A—H20B0.9300C19B—C24B1.353 (5)
C23A—C24A1.394 (7)C19B—C20B1.383 (6)
C23A—H23B0.9300C20B—C21B1.373 (6)
C24A—H24B0.9300C20B—H20A0.9300
C26A—H26D0.9600C21B—C22B1.387 (6)
C26A—H26E0.9600C22B—C23B1.353 (6)
C26A—H26F0.9600C23B—C24B1.393 (6)
O25C—C21C1.366 (7)C23B—H23A0.9300
O25C—C26C1.380 (7)C24B—H24A0.9300
C20C—C21C1.356 (8)C26B—H26A0.9600
C20C—H20C0.9300C26B—H26B0.9600
C23C—C24C1.394 (7)C26B—H26C0.9600
C23C—H23C0.9300C28B—H28A0.9600
C24C—H24C0.9300C28B—H28B0.9600
C26C—H26G0.9600C28B—H28C0.9600
C22A—O27A—C28A117.3 (4)H28D—C28A—H28F109.5
C13A—N12A—C11A121.3 (3)H28E—C28A—H28F109.5
C13A—N12A—H12A119.4C21B—O25B—C26B116.7 (4)
C11A—N12A—H12A119.4C22B—O27B—C28B117.0 (4)
O1A—C1A—C10A121.7 (4)C11B—N12B—C13B121.8 (3)
O1A—C1A—C2A120.4 (4)C11B—N12B—H12B119.1
C10A—C1A—C2A117.9 (4)C13B—N12B—H12B119.1
C1A—C2A—C3A113.8 (4)O1B—C1B—C10B120.7 (4)
C1A—C2A—H2AA108.8O1B—C1B—C2B121.0 (5)
C3A—C2A—H2AA108.8C10B—C1B—C2B118.2 (4)
C1A—C2A—H2AB108.8C1B—C2B—C3B113.8 (4)
C3A—C2A—H2AB108.8C1B—C2B—H2BA108.8
H2AA—C2A—H2AB107.7C3B—C2B—H2BA108.8
C4A—C3A—C16A109.1 (3)C1B—C2B—H2BB108.8
C4A—C3A—C15A111.0 (4)C3B—C2B—H2BB108.8
C16A—C3A—C15A109.4 (4)H2BA—C2B—H2BB107.7
C4A—C3A—C2A107.4 (4)C2B—C3B—C4B109.0 (4)
C16A—C3A—C2A110.2 (4)C2B—C3B—C16B110.0 (4)
C15A—C3A—C2A109.8 (4)C4B—C3B—C16B109.9 (4)
C11A—C4A—C3A112.9 (3)C2B—C3B—C15B108.5 (4)
C11A—C4A—H4AA109.0C4B—C3B—C15B110.8 (4)
C3A—C4A—H4AA109.0C16B—C3B—C15B108.7 (4)
C11A—C4A—H4AB109.0C11B—C4B—C3B112.5 (4)
C3A—C4A—H4AB109.0C11B—C4B—H4BA109.1
H4AA—C4A—H4AB107.8C3B—C4B—H4BA109.1
C13A—C5A—C6A112.3 (3)C11B—C4B—H4BB109.1
C13A—C5A—H5AA109.1C3B—C4B—H4BB109.1
C6A—C5A—H5AA109.1H4BA—C4B—H4BB107.8
C13A—C5A—H5AB109.1C13B—C5B—C6B114.1 (4)
C6A—C5A—H5AB109.1C13B—C5B—H5BA108.7
H5AA—C5A—H5AB107.9C6B—C5B—H5BA108.7
C7A—C6A—C5A108.0 (4)C13B—C5B—H5BB108.7
C7A—C6A—C17A110.4 (3)C6B—C5B—H5BB108.7
C5A—C6A—C17A110.5 (4)H5BA—C5B—H5BB107.6
C7A—C6A—C18A108.9 (4)C18B—C6B—C17B110.3 (4)
C5A—C6A—C18A108.9 (3)C18B—C6B—C7B110.3 (4)
C17A—C6A—C18A110.1 (4)C17B—C6B—C7B108.8 (4)
C8A—C7A—C6A114.3 (3)C18B—C6B—C5B109.5 (4)
C8A—C7A—H7AA108.7C17B—C6B—C5B111.2 (4)
C6A—C7A—H7AA108.7C7B—C6B—C5B106.6 (4)
C8A—C7A—H7AB108.7C8B—C7B—C6B114.6 (4)
C6A—C7A—H7AB108.7C8B—C7B—H7BA108.6
H7AA—C7A—H7AB107.6C6B—C7B—H7BA108.6
O8A—C8A—C14A121.7 (4)C8B—C7B—H7BB108.6
O8A—C8A—C7A120.4 (4)C6B—C7B—H7BB108.6
C14A—C8A—C7A117.7 (3)H7BA—C7B—H7BB107.6
C19A—C9A—C14A111.1 (3)O8B—C8B—C14B120.5 (5)
C19A—C9A—C10A112.0 (3)O8B—C8B—C7B121.4 (4)
C14A—C9A—C10A109.2 (3)C14B—C8B—C7B118.1 (4)
C19A—C9A—H9AA108.1C14B—C9B—C19B113.1 (4)
C14A—C9A—H9AA108.1C14B—C9B—C10B109.9 (3)
C10A—C9A—H9AA108.1C19B—C9B—C10B110.4 (4)
C11A—C10A—C1A119.4 (4)C14B—C9B—H9BA107.8
C11A—C10A—C9A121.7 (4)C19B—C9B—H9BA107.8
C1A—C10A—C9A118.9 (3)C10B—C9B—H9BA107.8
C10A—C11A—N12A120.0 (4)C11B—C10B—C1B119.6 (4)
C10A—C11A—C4A124.5 (4)C11B—C10B—C9B120.8 (4)
N12A—C11A—C4A115.5 (3)C1B—C10B—C9B119.6 (4)
C14A—C13A—N12A121.0 (3)C10B—C11B—N12B120.4 (4)
C14A—C13A—C5A123.7 (4)C10B—C11B—C4B124.5 (4)
N12A—C13A—C5A115.2 (3)N12B—C11B—C4B115.1 (3)
C13A—C14A—C8A120.1 (3)C14B—C13B—N12B119.5 (4)
C13A—C14A—C9A120.9 (4)C14B—C13B—C5B124.5 (4)
C8A—C14A—C9A119.0 (3)N12B—C13B—C5B115.9 (3)
C3A—C15A—H15D109.5C13B—C14B—C8B118.9 (4)
C3A—C15A—H15E109.5C13B—C14B—C9B122.0 (4)
H15D—C15A—H15E109.5C8B—C14B—C9B119.0 (4)
C3A—C15A—H15F109.5C3B—C15B—H15A109.5
H15D—C15A—H15F109.5C3B—C15B—H15B109.5
H15E—C15A—H15F109.5H15A—C15B—H15B109.5
C3A—C16A—H16D109.5C3B—C15B—H15C109.5
C3A—C16A—H16E109.5H15A—C15B—H15C109.5
H16D—C16A—H16E109.5H15B—C15B—H15C109.5
C3A—C16A—H16F109.5C3B—C16B—H16A109.5
H16D—C16A—H16F109.5C3B—C16B—H16B109.5
H16E—C16A—H16F109.5H16A—C16B—H16B109.5
C6A—C17A—H17D109.5C3B—C16B—H16C109.5
C6A—C17A—H17E109.5H16A—C16B—H16C109.5
H17D—C17A—H17E109.5H16B—C16B—H16C109.5
C6A—C17A—H17F109.5C6B—C17B—H17A109.5
H17D—C17A—H17F109.5C6B—C17B—H17B109.5
H17E—C17A—H17F109.5H17A—C17B—H17B109.5
C6A—C18A—H18D109.5C6B—C17B—H17C109.5
C6A—C18A—H18E109.5H17A—C17B—H17C109.5
H18D—C18A—H18E109.5H17B—C17B—H17C109.5
C6A—C18A—H18F109.5C6B—C18B—H18A109.5
H18D—C18A—H18F109.5C6B—C18B—H18B109.5
H18E—C18A—H18F109.5H18A—C18B—H18B109.5
C24A—C19A—C20A118.2 (4)C6B—C18B—H18C109.5
C24A—C19A—C9A119.6 (4)H18A—C18B—H18C109.5
C20A—C19A—C9A122.1 (4)H18B—C18B—H18C109.5
O27A—C22A—C23A125.6 (5)C24B—C19B—C20B117.4 (4)
O27A—C22A—C21A117.0 (5)C24B—C19B—C9B122.9 (4)
C23A—C22A—C21A117.4 (5)C20B—C19B—C9B119.7 (4)
C21A—O25A—C26A119.4 (6)C21B—C20B—C19B122.1 (4)
C21A—C20A—C19A122.0 (5)C21B—C20B—H20A119.0
C21A—C20A—H20B119.0C19B—C20B—H20A119.0
C19A—C20A—H20B119.0C20B—C21B—O25B125.0 (4)
C20A—C21A—O25A124.8 (5)C20B—C21B—C22B119.7 (4)
C20A—C21A—C22A120.6 (5)O25B—C21B—C22B115.2 (4)
O25A—C21A—C22A114.6 (5)C23B—C22B—O27B124.5 (4)
C22A—C23A—C24A122.0 (5)C23B—C22B—C21B118.5 (5)
C22A—C23A—H23B119.0O27B—C22B—C21B117.1 (4)
C24A—C23A—H23B119.0C22B—C23B—C24B121.2 (4)
C19A—C24A—C23A119.8 (5)C22B—C23B—H23A119.4
C19A—C24A—H24B120.1C24B—C23B—H23A119.4
C23A—C24A—H24B120.1C19B—C24B—C23B121.2 (4)
C21C—O25C—C26C119.3 (6)C19B—C24B—H24A119.4
C21C—C20C—H20C119.0C23B—C24B—H24A119.4
C20C—C21C—O25C124.7 (5)O25B—C26B—H26A109.5
C24C—C23C—H23C119.1O25B—C26B—H26B109.5
C23C—C24C—H24C120.1H26A—C26B—H26B109.5
O25C—C26C—H26G109.5O25B—C26B—H26C109.5
O25C—C26C—H26H109.5H26A—C26B—H26C109.5
H26G—C26C—H26H109.5H26B—C26B—H26C109.5
O25C—C26C—H26I109.5O27B—C28B—H28A109.5
H26G—C26C—H26I109.5O27B—C28B—H28B109.5
H26H—C26C—H26I109.5H28A—C28B—H28B109.5
O27A—C28A—H28D109.5O27B—C28B—H28C109.5
O27A—C28A—H28E109.5H28A—C28B—H28C109.5
H28D—C28A—H28E109.5H28B—C28B—H28C109.5
O27A—C28A—H28F109.5
O1A—C1A—C2A—C3A148.7 (4)O1B—C1B—C2B—C3B151.5 (5)
C10A—C1A—C2A—C3A33.4 (6)C10B—C1B—C2B—C3B31.4 (6)
C1A—C2A—C3A—C4A54.9 (5)C1B—C2B—C3B—C4B53.3 (6)
C1A—C2A—C3A—C16A173.6 (4)C1B—C2B—C3B—C16B173.8 (4)
C1A—C2A—C3A—C15A65.9 (5)C1B—C2B—C3B—C15B67.4 (6)
C16A—C3A—C4A—C11A167.4 (4)C2B—C3B—C4B—C11B46.6 (5)
C15A—C3A—C4A—C11A72.0 (5)C16B—C3B—C4B—C11B167.2 (4)
C2A—C3A—C4A—C11A48.1 (5)C15B—C3B—C4B—C11B72.6 (5)
C13A—C5A—C6A—C7A49.7 (5)C13B—C5B—C6B—C18B166.2 (5)
C13A—C5A—C6A—C17A71.2 (4)C13B—C5B—C6B—C17B71.7 (5)
C13A—C5A—C6A—C18A167.8 (4)C13B—C5B—C6B—C7B46.8 (6)
C5A—C6A—C7A—C8A53.4 (5)C18B—C6B—C7B—C8B172.3 (4)
C17A—C6A—C7A—C8A67.5 (5)C17B—C6B—C7B—C8B66.5 (5)
C18A—C6A—C7A—C8A171.5 (4)C5B—C6B—C7B—C8B53.5 (5)
C6A—C7A—C8A—O8A156.3 (4)C6B—C7B—C8B—O8B146.9 (4)
C6A—C7A—C8A—C14A28.0 (6)C6B—C7B—C8B—C14B35.2 (6)
O1A—C1A—C10A—C11A179.4 (4)O1B—C1B—C10B—C11B178.2 (4)
C2A—C1A—C10A—C11A2.7 (6)C2B—C1B—C10B—C11B1.1 (7)
O1A—C1A—C10A—C9A0.3 (7)O1B—C1B—C10B—C9B3.2 (7)
C2A—C1A—C10A—C9A178.2 (4)C2B—C1B—C10B—C9B179.7 (4)
C19A—C9A—C10A—C11A100.3 (4)C14B—C9B—C10B—C11B24.2 (5)
C14A—C9A—C10A—C11A23.3 (6)C19B—C9B—C10B—C11B101.1 (5)
C19A—C9A—C10A—C1A78.8 (5)C14B—C9B—C10B—C1B157.2 (4)
C14A—C9A—C10A—C1A157.7 (4)C19B—C9B—C10B—C1B77.5 (5)
C1A—C10A—C11A—N12A174.4 (4)C1B—C10B—C11B—N12B172.4 (4)
C9A—C10A—C11A—N12A6.6 (6)C9B—C10B—C11B—N12B9.0 (6)
C1A—C10A—C11A—C4A3.5 (7)C1B—C10B—C11B—C4B5.0 (7)
C9A—C10A—C11A—C4A175.6 (4)C9B—C10B—C11B—C4B173.7 (4)
C13A—N12A—C11A—C10A12.7 (7)C13B—N12B—C11B—C10B10.4 (7)
C13A—N12A—C11A—C4A165.4 (4)C13B—N12B—C11B—C4B167.2 (4)
C3A—C4A—C11A—C10A21.3 (6)C3B—C4B—C11B—C10B19.3 (6)
C3A—C4A—C11A—N12A160.8 (4)C3B—C4B—C11B—N12B163.2 (4)
C11A—N12A—C13A—C14A11.7 (7)C11B—N12B—C13B—C14B11.4 (7)
C11A—N12A—C13A—C5A165.7 (4)C11B—N12B—C13B—C5B164.6 (4)
C6A—C5A—C13A—C14A22.1 (6)C6B—C5B—C13B—C14B23.1 (7)
C6A—C5A—C13A—N12A160.6 (4)C6B—C5B—C13B—N12B161.2 (4)
N12A—C13A—C14A—C8A171.2 (4)N12B—C13B—C14B—C8B176.4 (4)
C5A—C13A—C14A—C8A6.0 (6)C5B—C13B—C14B—C8B0.8 (7)
N12A—C13A—C14A—C9A8.4 (6)N12B—C13B—C14B—C9B7.3 (6)
C5A—C13A—C14A—C9A174.4 (4)C5B—C13B—C14B—C9B177.0 (4)
O8A—C8A—C14A—C13A172.4 (4)O8B—C8B—C14B—C13B175.3 (4)
C7A—C8A—C14A—C13A3.2 (6)C7B—C8B—C14B—C13B6.7 (6)
O8A—C8A—C14A—C9A7.2 (6)O8B—C8B—C14B—C9B1.0 (6)
C7A—C8A—C14A—C9A177.2 (4)C7B—C8B—C14B—C9B176.9 (4)
C19A—C9A—C14A—C13A100.0 (4)C19B—C9B—C14B—C13B100.3 (4)
C10A—C9A—C14A—C13A24.1 (5)C10B—C9B—C14B—C13B23.5 (6)
C19A—C9A—C14A—C8A80.4 (5)C19B—C9B—C14B—C8B75.9 (5)
C10A—C9A—C14A—C8A155.5 (4)C10B—C9B—C14B—C8B160.3 (4)
C14A—C9A—C19A—C24A100.4 (6)C14B—C9B—C19B—C24B128.4 (5)
C10A—C9A—C19A—C24A137.1 (6)C10B—C9B—C19B—C24B108.1 (5)
C14A—C9A—C19A—C20A77.3 (6)C14B—C9B—C19B—C20B49.7 (5)
C10A—C9A—C19A—C20A45.1 (6)C10B—C9B—C19B—C20B73.9 (5)
C28A—O27A—C22A—C23A16.7 (7)C24B—C19B—C20B—C21B1.9 (7)
C28A—O27A—C22A—C21A162.8 (6)C9B—C19B—C20B—C21B180.0 (4)
C24A—C19A—C20A—C21A0.00 (10)C19B—C20B—C21B—O25B179.1 (5)
C9A—C19A—C20A—C21A177.8 (3)C19B—C20B—C21B—C22B1.8 (8)
C19A—C20A—C21A—O25A180.00 (6)C26B—O25B—C21B—C20B7.2 (7)
C19A—C20A—C21A—C22A0.00 (11)C26B—O25B—C21B—C22B170.1 (5)
C26A—O25A—C21A—C20A0.4 (17)C28B—O27B—C22B—C23B15.7 (8)
C26A—O25A—C21A—C22A179.6 (17)C28B—O27B—C22B—C21B165.6 (5)
O27A—C22A—C21A—C20A179.5 (4)C20B—C21B—C22B—C23B1.7 (8)
C23A—C22A—C21A—C20A0.00 (9)O25B—C21B—C22B—C23B179.2 (5)
O27A—C22A—C21A—O25A0.5 (4)C20B—C21B—C22B—O27B179.5 (4)
C23A—C22A—C21A—O25A180.00 (5)O25B—C21B—C22B—O27B2.0 (7)
O27A—C22A—C23A—C24A179.5 (4)O27B—C22B—C23B—C24B179.5 (5)
C21A—C22A—C23A—C24A0.00 (9)C21B—C22B—C23B—C24B1.7 (9)
C20A—C19A—C24A—C23A0.00 (9)C20B—C19B—C24B—C23B1.9 (8)
C9A—C19A—C24A—C23A177.8 (3)C9B—C19B—C24B—C23B180.0 (5)
C22A—C23A—C24A—C19A0.00 (11)C22B—C23B—C24B—C19B1.9 (10)
C26C—O25C—C21C—C20C20 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12A—H12A···O1Ai0.862.072.846 (4)150
N12B—H12B···O8Bii0.862.052.885 (4)165
C2A—H2AA···O1Bii0.972.453.400 (6)166
C16A—H16D···O25Aiii0.962.613.477 (12)150
C7A—H7AB···O27Biv0.972.473.432 (6)169
C7B—H7BB···O8Ai0.972.573.507 (5)162
Symmetry codes: (i) x1/2, y+1, z; (ii) x+1/2, y, z; (iii) x+1/2, y, z1/2; (iv) x, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC25H31NO4
Mr409.51
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)293
a, b, c (Å)14.1607 (6), 15.3126 (10), 21.1196 (14)
V3)4579.5 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerOxford Diffraction Xcalibur Sapphire3
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.672, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14639, 6386, 4075
Rint0.055
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.127, 1.01
No. of reflections6386
No. of parameters604
No. of restraints53
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N12A—H12A···O1Ai0.862.072.846 (4)150
N12B—H12B···O8Bii0.862.052.885 (4)165
C2A—H2AA···O1Bii0.972.453.400 (6)166
C16A—H16D···O25Aiii0.962.613.477 (12)150
C7A—H7AB···O27Biv0.972.473.432 (6)169
C7B—H7BB···O8Ai0.972.573.507 (5)162
Symmetry codes: (i) x1/2, y+1, z; (ii) x+1/2, y, z; (iii) x+1/2, y, z1/2; (iv) x, y+1, z+1/2.
 

Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

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Volume 69| Part 2| February 2013| Pages o297-o298
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