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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-Formyl-r-2,c-6-bis­­(4-meth­oxy­phen­yl)-t-3-methyl­piperidin-4-one

aPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, Government Arts College (Autonomous), Coimbatore 641 018, Tamilnadu, India, and cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: athiru@vsnl.net

(Received 2 October 2009; accepted 15 October 2009; online 23 October 2009)

The asymmetric unit of the title compound, C21H23NO4, contains two crystallographically independent mol­ecules A and B. In both mol­ecules, the piperidine-4-one rings adopt a distorted twist-boat conformation. The formyl group at position 1, the methoxy­phenyl ring at position 2 and the methyl group at position 3 are attached equatorially. The meth­oxy phenyl ring at position 6 has an axial orientation. The dihedral angle between the two benzene rings is 55.27 (8)° in mol­ecule A, and 55.29 (8)° in mol­ecule B. In the crystal, the mol­ecules are linked by weak C—H⋯O inter­molecular hydrogen-bond inter­actions. In addition, weak C—H⋯π inter­molecular inter­actions involving the benzene rings at positions 6 and 2 of mol­ecule B are also found in the crystal structure.

Related literature

For the biological activity of piperidones, see: Aridoss et al. (2008[Aridoss, G., Amirthaganesan, S., Ashok Kumar, N., Kim, J. T., Lim, K. T., Kabilan, S. & Jeong, Y. T. (2008). Bioorg. Med. Chem. Lett. 18, 6542-6548.]). For anti­neoplastic agents, see: Pati et al. (2008[Pati, H. N., Das, U., Quail, J. W., Kawase, M., Sakagami, H. & Dimmock, J. R. (2008). Eur. J. Med. Chem. 43, 1-7.]). For the stereochemistry of piperidine-4-one, see: Ponnuswamy et al. (2002[Ponnuswamy, S., Venkatraj, M., Jeyaraman, R., Suresh Kumar, M., Kumaran, D. & Ponnuswamy, M. N. (2002). Indian J. Chem. Sect. B, 41, 614-627.]); Venkatraj et al. (2008[Venkatraj, M., Ponnuswamy, S. & Jeyaraman, R. (2008). Indian J. Chem. Sect. B, 47, 461-476.]).

[Scheme 1]

Experimental

Crystal data
  • C21H23NO4

  • Mr = 353.40

  • Triclinic, [P \overline 1]

  • a = 11.5409 (4) Å

  • b = 12.4972 (5) Å

  • c = 14.7816 (6) Å

  • α = 67.878 (4)°

  • β = 74.719 (3)°

  • γ = 67.123 (4)°

  • V = 1802.42 (14) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.73 mm−1

  • T = 110 K

  • 0.55 × 0.45 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.484, Tmax = 1.000

  • 13170 measured reflections

  • 7096 independent reflections

  • 6709 reflections with I > 2σ(I)

  • Rint = 0.020

Refinement
  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.127

  • S = 1.06

  • 7096 reflections

  • 477 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.69 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
C5A—H5B⋯O16Bi 0.99 2.47 3.351 (2) 148
C5B—H5C⋯O11Aii 0.99 2.34 3.222 (2) 148
C12B—H12D⋯O11Aiii 0.98 2.47 3.427 (2) 167
C16A—H16A⋯O12Biv 0.98 2.51 3.468 (2) 167
C16B—H16D⋯O16Av 0.98 2.47 3.334 (2) 147
C25A—H25A⋯O4Bvi 0.95 2.43 3.266 (2) 147
C2A—H2ACg1vii 1.00 2.71 3.714 (2) 178
C12A—H12BCg2viii 0.98 2.92 3.846 (2) 158
Symmetry codes: (i) x, y+1, z; (ii) x, y, z-1; (iii) x, y-1, z-1; (iv) -x+1, -y, -z; (v) -x+1, -y, -z+1; (vi) x-1, y, z+1; (vii) -x, -y+1, -z+1; (viii) x, y, z+1. Cg1 and Cg2 are the centroids of the C61B–C66B and C21B–C26B rings, respectively.

Data collection: CrysAlis Pro (Oxford Diffraction, 2009[Oxford Diffraction (2009). 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Piperidin-4-ones and their derivatives show a broad spectrum of biological activities which includes antimicrobial, antiviral, anti tuberculosis and anticancer activities and could also be used against multidrug resistant organisms (Aridoss et al., 2008). 2,6-Diarylpiperidin-4-one based chemical entities act as antineoplastic agents (Pati et al., 2008). Recent efforts devoted to 2,6-diarylpiperidin-4-one based chemical entities and establishing their stereochemistry (Ponnuswamy et al., 2002), (Venkatraj et al., 2008) are significant because the pharmacological effects of potential new drugs depends on the stereochemistry and ring conformations of these compounds.

The asymmetric unit of the title compound, C21H23NO4, contains two crystallographically independent molecules A and B (Fig. 1, Fig. 2). In both molecules, the piperidine ring adopts a distorted twist boat conformation. The formyl group at 1, the methoxy phenyl ring at 2 and the methyl group at 3 are attached equatorially. The methoxy phenyl ring at 6 has an axial orientation. The dihedral angle between the two benzene rings is 55.27 (8)° in molecule A; and 55.29 (8)° in molecule B. Compound(I) is chiral: in the arbitrarily chosen asymmetric molecules, C2A(C2B), C3A(C3B) and C6A(C6B) have S, R and R conformations respectively. The molecules are linked by weak C–H···O intermolecular hydrogen bond interactions (Fig. 3; Table 1). In addition, weak C2A-H2A···π and C12A-H12B···π intermolecular interactions involving the benzene rings at positions 6(C61B-C66B) and 2(C21B-C26B) of molecule B are also found in the crystal structure.

Related literature top

For the biological activity of piperidones, see: Aridoss et al. (2008). For antineoplastic agents, see: Pati et al. (2008). For the stereochemistry of piperidine-4-one, see: Ponnuswamy et al. (2002); Venkatraj et al. (2008). Cg1 and Cg2 are the centroids of the C61B--C66B and C21B–C26B rings, respectively.

Experimental top

The ice-cold solution of acetic-formic anhydride was prepared from acetic anhydride (10 ml) and 85% formic acid (5 ml) and was added slowly to a cold solution of r-2,c-6-bis(4-methoxyphenyl)-t-3-methylpiperidin-4-one (1.625 g, 0.005 mol) in benzene (30 ml). The reaction mixture was stirred at room temperature for 5 h. The organic layer was separated, dried over anhydrous Na2SO4 and concentrated. The resulting mass was purified by crystallization from benzene-petroleum ether (333–335 K) in the ratio 1:1. Yield obtained was 1.13 g (64%).

Refinement top

Atoms H11A at C11A and H11B at C11B were located in a difference Fourier map and refined isotropically. Remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95, 0.98, 0.99 and 1.00 Å for Csp2, methyl, methylene and methine C, respectively; Uiso(H) = kUeq(C), where k = 1.5 for methyl and 1.2 for all other H atoms. The maximum residual electron density peak 0.685 e Å-3 is located 2.23Å from H5A.

Structure description top

Piperidin-4-ones and their derivatives show a broad spectrum of biological activities which includes antimicrobial, antiviral, anti tuberculosis and anticancer activities and could also be used against multidrug resistant organisms (Aridoss et al., 2008). 2,6-Diarylpiperidin-4-one based chemical entities act as antineoplastic agents (Pati et al., 2008). Recent efforts devoted to 2,6-diarylpiperidin-4-one based chemical entities and establishing their stereochemistry (Ponnuswamy et al., 2002), (Venkatraj et al., 2008) are significant because the pharmacological effects of potential new drugs depends on the stereochemistry and ring conformations of these compounds.

The asymmetric unit of the title compound, C21H23NO4, contains two crystallographically independent molecules A and B (Fig. 1, Fig. 2). In both molecules, the piperidine ring adopts a distorted twist boat conformation. The formyl group at 1, the methoxy phenyl ring at 2 and the methyl group at 3 are attached equatorially. The methoxy phenyl ring at 6 has an axial orientation. The dihedral angle between the two benzene rings is 55.27 (8)° in molecule A; and 55.29 (8)° in molecule B. Compound(I) is chiral: in the arbitrarily chosen asymmetric molecules, C2A(C2B), C3A(C3B) and C6A(C6B) have S, R and R conformations respectively. The molecules are linked by weak C–H···O intermolecular hydrogen bond interactions (Fig. 3; Table 1). In addition, weak C2A-H2A···π and C12A-H12B···π intermolecular interactions involving the benzene rings at positions 6(C61B-C66B) and 2(C21B-C26B) of molecule B are also found in the crystal structure.

For the biological activity of piperidones, see: Aridoss et al. (2008). For antineoplastic agents, see: Pati et al. (2008). For the stereochemistry of piperidine-4-one, see: Ponnuswamy et al. (2002); Venkatraj et al. (2008). Cg1 and Cg2 are the centroids of the C61B--C66B and C21B–C26B rings, respectively.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of independent molecule A, showing the atom-numbering scheme and displacement ellipsoids drawn at the 40% probability level(arbitary spheres for H atoms).
[Figure 2] Fig. 2. The molecular structure of independent molecule B, showing the atom-numbering scheme and displacement ellipsoids drawn at the 40% probability level(arbitary spheres for H atoms).
[Figure 3] Fig. 3. The packing of the title compound, viewed down the a axis. Dashed lines indicate weak C–H···O hydrogen bond intermolecular interactions. H atoms not involved in hydrogen bonding have been omitted.
1-Formyl-r-2,c-6-bis(4-methoxyphenyl)-t-3- methylpiperidin-4-one top
Crystal data top
C21H23NO4Z = 4
Mr = 353.40F(000) = 752
Triclinic, P1Dx = 1.302 Mg m3
Hall symbol: -P 1Melting point: 382(1) K
a = 11.5409 (4) ÅCu Kα radiation, λ = 1.54184 Å
b = 12.4972 (5) ÅCell parameters from 11847 reflections
c = 14.7816 (6) Åθ = 4.7–74.0°
α = 67.878 (4)°µ = 0.73 mm1
β = 74.719 (3)°T = 110 K
γ = 67.123 (4)°Plate, colourless
V = 1802.42 (14) Å30.55 × 0.45 × 0.18 mm
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
7096 independent reflections
Radiation source: Enhance (Cu) X-ray Source6709 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
Detector resolution: 10.5081 pixels mm-1θmax = 74.2°, θmin = 4.7°
ω scansh = 1413
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 1511
Tmin = 0.484, Tmax = 1.000l = 1817
13170 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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0704P)2 + 1.0073P]
where P = (Fo2 + 2Fc2)/3
7096 reflections(Δ/σ)max = 0.001
477 parametersΔρmax = 0.69 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C21H23NO4γ = 67.123 (4)°
Mr = 353.40V = 1802.42 (14) Å3
Triclinic, P1Z = 4
a = 11.5409 (4) ÅCu Kα radiation
b = 12.4972 (5) ŵ = 0.73 mm1
c = 14.7816 (6) ÅT = 110 K
α = 67.878 (4)°0.55 × 0.45 × 0.18 mm
β = 74.719 (3)°
Data collection top
Oxford Diffraction Xcalibur Ruby Gemini
diffractometer
7096 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
6709 reflections with I > 2σ(I)
Tmin = 0.484, Tmax = 1.000Rint = 0.020
13170 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.69 e Å3
7096 reflectionsΔρmin = 0.24 e Å3
477 parameters
Special details top

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 of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O4A0.07324 (12)0.89236 (11)0.42627 (9)0.0348 (4)
O11A0.22078 (11)0.58074 (10)0.77936 (8)0.0257 (3)
O12A0.13915 (10)0.19373 (10)0.83970 (9)0.0263 (3)
O16A0.50084 (11)0.34114 (10)0.38966 (8)0.0278 (3)
N1A0.08853 (11)0.63526 (11)0.66747 (9)0.0179 (3)
C2A0.03768 (13)0.64345 (13)0.65383 (10)0.0173 (4)
C3A0.05318 (13)0.69301 (13)0.54299 (10)0.0190 (4)
C4A0.01771 (14)0.80912 (14)0.49119 (11)0.0225 (4)
C5A0.09180 (15)0.81439 (13)0.52509 (11)0.0234 (4)
C6A0.17338 (14)0.69007 (13)0.58437 (10)0.0198 (4)
C11A0.11909 (14)0.59241 (13)0.75955 (11)0.0200 (4)
C12A0.04601 (17)0.08158 (15)0.83098 (14)0.0340 (5)
C16A0.50805 (16)0.36516 (16)0.28637 (12)0.0299 (5)
C21A0.05983 (13)0.52092 (13)0.70245 (10)0.0168 (4)
C22A0.01942 (13)0.41768 (13)0.67499 (10)0.0188 (4)
C23A0.00377 (13)0.30662 (13)0.71881 (11)0.0191 (4)
C24A0.10739 (13)0.29805 (13)0.79199 (11)0.0187 (4)
C25A0.18706 (13)0.40017 (14)0.82045 (10)0.0200 (4)
C26A0.16288 (13)0.50999 (13)0.77538 (10)0.0187 (4)
C31A0.18659 (15)0.70981 (16)0.52986 (12)0.0267 (4)
C61A0.25694 (13)0.60156 (13)0.52662 (11)0.0194 (4)
C62A0.26778 (13)0.62969 (14)0.42518 (11)0.0213 (4)
C63A0.34838 (14)0.54553 (14)0.37608 (11)0.0224 (4)
C64A0.41988 (13)0.43110 (14)0.42926 (11)0.0212 (4)
C65A0.41148 (14)0.40143 (14)0.53153 (11)0.0233 (4)
C66A0.33148 (14)0.48552 (14)0.57865 (11)0.0219 (4)
O4B0.53820 (11)0.36112 (12)0.07942 (10)0.0332 (4)
O11B0.01487 (10)0.36764 (10)0.00291 (8)0.0257 (3)
O12B0.27346 (11)0.14716 (10)0.18039 (8)0.0274 (3)
O16B0.30583 (13)0.04338 (11)0.39872 (9)0.0349 (4)
N1B0.20061 (11)0.30115 (10)0.04000 (8)0.0165 (3)
C2B0.30548 (13)0.25962 (12)0.11508 (10)0.0162 (3)
C3B0.43640 (13)0.23049 (13)0.08605 (10)0.0179 (3)
C4B0.44154 (14)0.33596 (13)0.06091 (10)0.0193 (4)
C5B0.31987 (13)0.40727 (12)0.01243 (10)0.0183 (4)
C6B0.22404 (13)0.33873 (12)0.03542 (10)0.0167 (4)
C11B0.07901 (14)0.32711 (13)0.05147 (11)0.0196 (4)
C12B0.24507 (19)0.24519 (15)0.09881 (13)0.0332 (5)
C16B0.39847 (19)0.06051 (17)0.45455 (13)0.0389 (5)
C21B0.29772 (12)0.14959 (12)0.13105 (10)0.0167 (4)
C22B0.29169 (14)0.04595 (13)0.05153 (10)0.0195 (4)
C23B0.28509 (14)0.05628 (13)0.06458 (11)0.0200 (4)
C24B0.28423 (13)0.05435 (13)0.15938 (11)0.0194 (4)
C25B0.29209 (13)0.04776 (13)0.23975 (11)0.0200 (4)
C26B0.29897 (13)0.14859 (13)0.22514 (10)0.0180 (4)
C31B0.54440 (14)0.19367 (15)0.16552 (12)0.0255 (4)
C61B0.25660 (13)0.23214 (12)0.12884 (10)0.0173 (4)
C62B0.36078 (13)0.20273 (13)0.17407 (11)0.0196 (4)
C63B0.38102 (14)0.11155 (14)0.26463 (11)0.0228 (4)
C64B0.29614 (15)0.04691 (13)0.31014 (11)0.0235 (4)
C65B0.19218 (15)0.07336 (14)0.26483 (11)0.0252 (4)
C66B0.17247 (14)0.16488 (14)0.17595 (11)0.0215 (4)
H2A0.103630.702560.686750.0207*
H3A0.007550.629760.511920.0228*
H5A0.057910.869710.566160.0280*
H5B0.146290.849770.466610.0280*
H6A0.231490.706030.613700.0238*
H11A0.0512 (17)0.5705 (16)0.8096 (13)0.019 (4)*
H12A0.080330.014380.868160.0509*
H12B0.029790.067850.857410.0509*
H12C0.023410.085320.761380.0509*
H16A0.568750.294070.267290.0448*
H16B0.536200.436450.250030.0448*
H16C0.424140.381480.270850.0448*
H22A0.090480.423280.625500.0226*
H23A0.050590.237250.698990.0230*
H25A0.257580.394500.870490.0240*
H26A0.217960.579510.794710.0225*
H31A0.204970.632940.564330.0400*
H31B0.191980.733570.459520.0400*
H31C0.248500.773710.557300.0400*
H62A0.219280.708000.388190.0256*
H63A0.354090.566690.306600.0268*
H65A0.460830.323480.568370.0279*
H66A0.326640.464470.648050.0263*
H2B0.296440.327580.178820.0194*
H3B0.446980.158570.024940.0214*
H5C0.280800.484410.062440.0220*
H5D0.339580.428670.038530.0220*
H6B0.142410.398960.054270.0200*
H11B0.0730 (16)0.3100 (15)0.1086 (13)0.014 (4)*
H12D0.239930.305650.123430.0498*
H12E0.163640.213100.060620.0498*
H12F0.312220.283850.056580.0498*
H16D0.395810.127640.515950.0584*
H16E0.380450.014580.469980.0584*
H16F0.482960.080260.416160.0584*
H22B0.292080.044970.012960.0233*
H23B0.281230.126270.009660.0240*
H25B0.292760.048500.304390.0240*
H26B0.304600.217910.280240.0217*
H31D0.537350.125700.179180.0382*
H31E0.626060.168340.142470.0382*
H31F0.539070.263350.225890.0382*
H62B0.420030.245740.142650.0234*
H63B0.452320.094000.294740.0273*
H65B0.134680.028270.295200.0302*
H66B0.100790.182600.146230.0258*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O4A0.0407 (7)0.0275 (6)0.0286 (6)0.0091 (5)0.0121 (5)0.0025 (5)
O11A0.0285 (6)0.0313 (6)0.0210 (5)0.0145 (5)0.0062 (4)0.0053 (4)
O12A0.0195 (5)0.0203 (5)0.0354 (6)0.0107 (4)0.0024 (4)0.0044 (4)
O16A0.0277 (6)0.0263 (6)0.0245 (6)0.0058 (5)0.0009 (4)0.0074 (4)
N1A0.0186 (6)0.0197 (6)0.0160 (6)0.0105 (5)0.0000 (4)0.0034 (4)
C2A0.0166 (6)0.0183 (7)0.0162 (6)0.0068 (5)0.0006 (5)0.0053 (5)
C3A0.0176 (7)0.0213 (7)0.0162 (7)0.0060 (5)0.0003 (5)0.0056 (5)
C4A0.0240 (7)0.0211 (7)0.0173 (7)0.0055 (6)0.0011 (5)0.0051 (6)
C5A0.0269 (8)0.0188 (7)0.0222 (7)0.0111 (6)0.0001 (6)0.0025 (6)
C6A0.0205 (7)0.0221 (7)0.0181 (7)0.0131 (6)0.0006 (5)0.0024 (5)
C11A0.0235 (7)0.0191 (7)0.0183 (7)0.0101 (6)0.0009 (6)0.0048 (5)
C12A0.0325 (9)0.0210 (8)0.0438 (10)0.0131 (7)0.0074 (7)0.0090 (7)
C16A0.0247 (8)0.0368 (9)0.0269 (8)0.0067 (7)0.0006 (6)0.0139 (7)
C21A0.0168 (6)0.0189 (7)0.0160 (6)0.0080 (5)0.0019 (5)0.0048 (5)
C22A0.0162 (6)0.0220 (7)0.0180 (7)0.0083 (5)0.0024 (5)0.0069 (5)
C23A0.0181 (7)0.0188 (7)0.0212 (7)0.0062 (5)0.0019 (5)0.0072 (5)
C24A0.0172 (7)0.0200 (7)0.0206 (7)0.0095 (5)0.0045 (5)0.0032 (5)
C25A0.0155 (6)0.0254 (7)0.0181 (7)0.0091 (5)0.0016 (5)0.0057 (6)
C26A0.0163 (6)0.0216 (7)0.0186 (7)0.0065 (5)0.0001 (5)0.0079 (5)
C31A0.0204 (7)0.0344 (8)0.0227 (7)0.0077 (6)0.0033 (6)0.0070 (6)
C61A0.0161 (6)0.0225 (7)0.0196 (7)0.0115 (5)0.0001 (5)0.0028 (5)
C62A0.0168 (7)0.0241 (7)0.0201 (7)0.0081 (6)0.0027 (5)0.0021 (6)
C63A0.0191 (7)0.0299 (8)0.0176 (7)0.0114 (6)0.0020 (5)0.0036 (6)
C64A0.0160 (7)0.0249 (7)0.0236 (7)0.0106 (6)0.0012 (5)0.0071 (6)
C65A0.0207 (7)0.0223 (7)0.0227 (7)0.0088 (6)0.0035 (6)0.0003 (6)
C66A0.0213 (7)0.0263 (7)0.0169 (7)0.0122 (6)0.0011 (5)0.0017 (6)
O4B0.0254 (6)0.0402 (7)0.0431 (7)0.0214 (5)0.0049 (5)0.0178 (6)
O11B0.0164 (5)0.0288 (6)0.0305 (6)0.0063 (4)0.0005 (4)0.0113 (5)
O12B0.0398 (7)0.0208 (5)0.0265 (6)0.0145 (5)0.0011 (5)0.0099 (4)
O16B0.0435 (7)0.0303 (6)0.0246 (6)0.0189 (5)0.0075 (5)0.0072 (5)
N1B0.0163 (6)0.0160 (5)0.0174 (5)0.0061 (4)0.0008 (4)0.0055 (4)
C2B0.0162 (6)0.0148 (6)0.0159 (6)0.0059 (5)0.0001 (5)0.0033 (5)
C3B0.0158 (6)0.0182 (6)0.0180 (6)0.0068 (5)0.0002 (5)0.0042 (5)
C4B0.0206 (7)0.0200 (7)0.0172 (6)0.0109 (5)0.0016 (5)0.0019 (5)
C5B0.0224 (7)0.0144 (6)0.0188 (7)0.0087 (5)0.0032 (5)0.0027 (5)
C6B0.0162 (6)0.0158 (6)0.0186 (7)0.0059 (5)0.0003 (5)0.0066 (5)
C11B0.0185 (7)0.0176 (7)0.0221 (7)0.0069 (5)0.0027 (5)0.0044 (5)
C12B0.0491 (10)0.0246 (8)0.0339 (9)0.0223 (8)0.0018 (8)0.0096 (7)
C16B0.0447 (10)0.0321 (9)0.0283 (9)0.0106 (8)0.0131 (8)0.0067 (7)
C21B0.0137 (6)0.0148 (6)0.0198 (7)0.0046 (5)0.0004 (5)0.0047 (5)
C22B0.0219 (7)0.0185 (7)0.0168 (7)0.0074 (5)0.0009 (5)0.0045 (5)
C23B0.0213 (7)0.0153 (6)0.0207 (7)0.0076 (5)0.0003 (5)0.0027 (5)
C24B0.0162 (6)0.0167 (6)0.0254 (7)0.0050 (5)0.0007 (5)0.0095 (6)
C25B0.0196 (7)0.0209 (7)0.0187 (7)0.0056 (5)0.0007 (5)0.0076 (5)
C26B0.0161 (6)0.0167 (6)0.0178 (7)0.0054 (5)0.0002 (5)0.0032 (5)
C31B0.0187 (7)0.0324 (8)0.0266 (8)0.0098 (6)0.0034 (6)0.0132 (7)
C61B0.0191 (7)0.0150 (6)0.0171 (7)0.0061 (5)0.0017 (5)0.0063 (5)
C62B0.0174 (7)0.0179 (7)0.0208 (7)0.0071 (5)0.0025 (5)0.0052 (5)
C63B0.0195 (7)0.0217 (7)0.0229 (7)0.0044 (6)0.0030 (6)0.0046 (6)
C64B0.0289 (8)0.0179 (7)0.0187 (7)0.0082 (6)0.0007 (6)0.0022 (6)
C65B0.0301 (8)0.0243 (7)0.0229 (7)0.0174 (6)0.0022 (6)0.0042 (6)
C66B0.0233 (7)0.0237 (7)0.0207 (7)0.0118 (6)0.0004 (6)0.0077 (6)
Geometric parameters (Å, º) top
O4A—C4A1.212 (2)C25A—H25A0.9500
O11A—C11A1.225 (2)C26A—H26A0.9500
O12A—C12A1.424 (2)C31A—H31C0.9800
O12A—C24A1.369 (2)C31A—H31B0.9800
O16A—C16A1.427 (2)C31A—H31A0.9800
O16A—C64A1.368 (2)C62A—H62A0.9500
O4B—C4B1.211 (2)C63A—H63A0.9500
O11B—C11B1.224 (2)C65A—H65A0.9500
O12B—C24B1.364 (2)C66A—H66A0.9500
O12B—C12B1.433 (2)C2B—C3B1.548 (2)
O16B—C16B1.423 (3)C2B—C21B1.519 (2)
O16B—C64B1.366 (2)C3B—C4B1.523 (2)
N1A—C2A1.482 (2)C3B—C31B1.528 (2)
N1A—C6A1.480 (2)C4B—C5B1.502 (2)
N1A—C11A1.349 (2)C5B—C6B1.525 (2)
N1B—C2B1.4843 (19)C6B—C61B1.524 (2)
N1B—C6B1.4794 (19)C21B—C22B1.394 (2)
N1B—C11B1.354 (2)C21B—C26B1.392 (2)
C2A—C21A1.518 (2)C22B—C23B1.394 (2)
C2A—C3A1.5505 (19)C23B—C24B1.395 (2)
C3A—C4A1.523 (2)C24B—C25B1.393 (2)
C3A—C31A1.526 (3)C25B—C26B1.390 (2)
C4A—C5A1.509 (3)C61B—C62B1.387 (2)
C5A—C6A1.530 (2)C61B—C66B1.404 (2)
C6A—C61A1.527 (2)C62B—C63B1.398 (2)
C21A—C22A1.395 (2)C63B—C64B1.387 (2)
C21A—C26A1.391 (2)C64B—C65B1.395 (3)
C22A—C23A1.392 (2)C65B—C66B1.382 (2)
C23A—C24A1.394 (2)C2B—H2B1.0000
C24A—C25A1.393 (2)C3B—H3B1.0000
C25A—C26A1.384 (2)C5B—H5C0.9900
C61A—C62A1.388 (2)C5B—H5D0.9900
C61A—C66A1.405 (2)C6B—H6B1.0000
C62A—C63A1.399 (2)C11B—H11B0.971 (18)
C63A—C64A1.386 (2)C12B—H12D0.9800
C64A—C65A1.400 (2)C12B—H12E0.9800
C65A—C66A1.378 (2)C12B—H12F0.9800
C2A—H2A1.0000C16B—H16D0.9800
C3A—H3A1.0000C16B—H16E0.9800
C5A—H5B0.9900C16B—H16F0.9800
C5A—H5A0.9900C22B—H22B0.9500
C6A—H6A1.0000C23B—H23B0.9500
C11A—H11A0.97 (2)C25B—H25B0.9500
C12A—H12B0.9800C26B—H26B0.9500
C12A—H12A0.9800C31B—H31D0.9800
C12A—H12C0.9800C31B—H31E0.9800
C16A—H16B0.9800C31B—H31F0.9800
C16A—H16C0.9800C62B—H62B0.9500
C16A—H16A0.9800C63B—H63B0.9500
C22A—H22A0.9500C65B—H65B0.9500
C23A—H23A0.9500C66B—H66B0.9500
O4B···C25Ai3.266 (2)C66B···H2Avii2.8600
O11A···C5Bii3.2221 (18)H2A···H11A2.5200
O11A···C66A3.3659 (19)H2A···H26A2.3000
O11A···C16Aiii3.278 (2)H2A···C64Bvii3.0600
O11B···C12Biv3.309 (3)H2A···C65Bvii2.8800
O11B···C66B3.378 (2)H2A···C66Bvii2.8600
O16A···C16Bv3.334 (2)H2A···C61Bvii3.0400
O16B···C5Avi3.351 (2)H2A···H31C2.5500
O4A···H31C2.8500H2B···H26B2.3500
O4A···H12Cvii2.6500H2B···H11B2.5800
O4A···H31B2.6600H2B···O11Axv2.8000
O4A···H23Avii2.7900H2B···C5B3.0900
O4B···H23Bviii2.9100H2B···C11Axv3.0700
O4B···H31E2.6400H2B···H31F2.5700
O4B···H31F2.8600H2B···H66Axv2.5100
O4B···H16Bix2.8500H3A···C61A2.8200
O4B···H12Fviii2.6500H3A···C6A2.8600
O4B···H25Ai2.4300H3A···C22A2.8200
O11A···H5Cii2.3400H3A···H22A2.4600
O11A···H6A2.3600H3A···C62A2.9400
O11A···H66A2.6200H3B···C22B2.8500
O11A···H16Biii2.6600H3B···C6B2.8800
O11A···H2Bii2.8000H3B···H22B2.5200
O11A···H12Dx2.4700H3B···C61B2.8700
O11B···H12Eiv2.8200H3B···C62B3.0300
O11B···H6Bxi2.6200H5B···O16Bxiv2.4700
O11B···H66B2.6500H5B···C62A2.7800
O11B···H6B2.3500H5B···H62A2.2500
O12A···H31Exii2.7800H5C···C2B3.0800
O12A···H23Bxiii2.6500H5C···C12Bxiv3.0900
O12B···H16Aviii2.5100H5C···O11Axv2.3400
O16A···H16Dv2.4700H5C···H12Dxiv2.3200
O16A···H6Aiii2.9000H5D···H26Avii2.4800
O16B···H5Bvi2.4700H5D···H62B2.2200
N1A···H22A2.9300H5D···C62B2.7400
N1A···H66A2.7700H6A···O16Aiii2.9000
N1B···H66B2.7700H6A···O11A2.3600
N1B···H22B2.8100H6B···O11B2.3500
C3A···C61A3.278 (2)H6B···O11Bxi2.6200
C3A···C62A3.569 (2)H6B···H11Avii2.5900
C3B···C61B3.307 (2)H11A···C11Bii2.908 (19)
C4A···C62A3.323 (2)H11A···C21A2.64 (2)
C4B···C62B3.294 (2)H11A···C26A3.06 (2)
C5A···O16Bxiv3.351 (2)H11A···H2A2.5200
C5B···O11Axv3.2221 (18)H11A···H6Bvii2.5900
C11A···C66A3.411 (2)H11B···H2B2.5800
C11A···C11Bii3.542 (2)H11B···C25Axv3.09 (2)
C11A···C22A3.524 (2)H11B···C22Axv3.095 (18)
C11B···C66B3.414 (2)H11B···C23Axv2.932 (19)
C11B···C11Axv3.542 (2)H11B···C21B2.619 (19)
C11B···C22B3.416 (2)H11B···C24Axv2.92 (2)
C12A···C24Bii3.536 (3)H12B···C24Bii2.7300
C12B···O11Biv3.309 (3)H12B···C25Bii2.9500
C16A···O11Aiii3.278 (2)H12B···C23Bii3.0500
C16B···O16Av3.334 (2)H12B···C23A2.8600
C22A···C11A3.524 (2)H12B···H23A2.5300
C22B···C11B3.416 (2)H12C···H23A2.1700
C23A···C26Bii3.424 (2)H12C···C23A2.6800
C24B···C12Axv3.536 (3)H12C···O4Avii2.6500
C25A···O4Bxii3.266 (2)H12D···O11Axvi2.4700
C25A···C63Avii3.571 (2)H12D···H5Cvi2.3200
C25B···C63Bviii3.509 (2)H12E···C23B2.8000
C26A···C31A3.556 (2)H12E···H23B2.4300
C26B···C31B3.471 (2)H12E···O11Biv2.8200
C26B···C23Axv3.424 (2)H12F···H23B2.2000
C31A···C26A3.556 (2)H12F···O4Bviii2.6500
C31A···C64Avii3.570 (3)H12F···C23B2.7000
C31B···C26B3.471 (2)H16A···O12Bviii2.5100
C61A···C3A3.278 (2)H16A···C12Bviii2.9100
C61B···C3B3.307 (2)H16B···C63A2.7400
C62A···C4A3.323 (2)H16B···O11Aiii2.6600
C62A···C3A3.569 (2)H16B···H63A2.2800
C62B···C4B3.294 (2)H16B···O4Bix2.8500
C63A···C25Avii3.571 (2)H16C···C26Avii2.9300
C63B···C25Bviii3.509 (2)H16C···C63A2.7700
C64A···C66Aiii3.375 (2)H16C···H63A2.3500
C64A···C31Avii3.570 (3)H16D···O16Av2.4700
C65A···C66Aiii3.525 (2)H16E···H63B2.4400
C65A···C65Aiii3.506 (2)H16E···H31Cvii2.4200
C66A···C64Aiii3.375 (2)H16E···C63B2.8100
C66A···O11A3.3659 (19)H16F···H63B2.2100
C66A···C11A3.411 (2)H16F···C63B2.7000
C66A···C65Aiii3.525 (2)H22A···C3A3.0400
C66B···O11B3.378 (2)H22A···N1A2.9300
C66B···C11B3.414 (2)H22A···H3A2.4600
C2B···H5C3.0800H22A···C31Avii3.0600
C3A···H22A3.0400H22A···C66A3.0100
C3B···H22B3.0700H22A···H31Bvii2.4700
C4A···H62A2.8200H22B···N1B2.8100
C4B···H62B2.7700H22B···C3B3.0700
C5A···H62A2.6400H22B···C66B3.0500
C5B···H2B3.0900H22B···H3B2.5200
C5B···H62B2.6000H23A···C26Bii3.0000
C6A···H3A2.8600H23A···C12A2.5500
C6B···H26Avii3.0200H23A···C25Bii2.9600
C6B···H3B2.8800H23A···H12B2.5300
C11A···H66A2.8200H23A···H12C2.1700
C11A···H2Bii3.0700H23A···O4Avii2.7900
C11B···H66B2.8100H23A···H31Bvii2.4700
C11B···H11Axv2.908 (19)H23B···O12Axiii2.6500
C12A···H23A2.5500H23B···H31Eviii2.5300
C12B···H16Aviii2.9100H23B···H12F2.2000
C12B···H5Cvi3.0900H23B···C12B2.5200
C12B···H23B2.5200H23B···H12E2.4300
C16A···H63A2.5300H23B···O4Bviii2.9100
C16B···H63B2.5300H25A···O4Bxii2.4300
C21A···H31A2.6000H26A···C6Bvii3.0200
C21A···H11A2.64 (2)H26A···H2A2.3000
C21B···H31D2.5900H26A···H5Dvii2.4800
C21B···H11B2.619 (19)H26A···C61Bvii2.8200
C22A···H3A2.8200H26A···C62Bvii2.7200
C22A···H31Bvii3.0500H26B···H2B2.3500
C22A···H11Bii3.095 (18)H31A···C21A2.6000
C22B···H3B2.8500H31A···C26A2.9900
C23A···H12B2.8600H31A···C63Avii3.0200
C23A···H11Bii2.932 (19)H31A···C64Avii2.8600
C23A···H31Bvii3.0500H31B···O4A2.6600
C23A···H12C2.6800H31B···C22Avii3.0500
C23B···H12Bxv3.0500H31B···C23Avii3.0500
C23B···H12E2.8000H31B···H22Avii2.4700
C23B···H12F2.7000H31B···H23Avii2.4700
C24A···H11Bii2.92 (2)H31C···O4A2.8500
C24B···H12Bxv2.7300H31C···H2A2.5500
C25A···H11Bii3.09 (2)H31C···H16Evii2.4200
C25A···H63Avii2.8500H31D···C21B2.5900
C25B···H23Axv2.9600H31D···C26B2.8900
C25B···H63Bviii2.8700H31E···H23Bviii2.5300
C25B···H12Bxv2.9500H31E···O4B2.6400
C26A···H16Cvii2.9300H31E···O12Ai2.7800
C26A···H31A2.9900H31F···H2B2.5700
C26A···H11A3.06 (2)H31F···C63Aix3.0400
C26B···H23Axv3.0000H31F···O4B2.8600
C26B···H31D2.8900H62A···C4A2.8200
C31A···H22Avii3.0600H62A···C5A2.6400
C61A···H3A2.8200H62A···H5B2.2500
C61B···H26Avii2.8200H62B···C4B2.7700
C61B···H3B2.8700H62B···C5B2.6000
C61B···H2Avii3.0400H62B···H5D2.2200
C62A···H5B2.7800H63A···C25Avii2.8500
C62A···H3A2.9400H63A···C16A2.5300
C62B···H5D2.7400H63A···H16B2.2800
C62B···H26Avii2.7200H63A···H16C2.3500
C62B···H3B3.0300H63B···H16E2.4400
C63A···H16C2.7700H63B···H16F2.2100
C63A···H16B2.7400H63B···C25Bviii2.8700
C63A···H31Avii3.0200H63B···C16B2.5300
C63A···H31Fix3.0400H66A···O11A2.6200
C63B···H16F2.7000H66A···N1A2.7700
C63B···H16E2.8100H66A···C11A2.8200
C64A···H31Avii2.8600H66A···H2Bii2.5100
C64B···H2Avii3.0600H66B···O11B2.6500
C65B···H2Avii2.8800H66B···N1B2.7700
C66A···H22A3.0100H66B···C11B2.8100
C66B···H22B3.0500
C12A—O12A—C24A117.51 (14)C64A—C63A—H63A120.00
C16A—O16A—C64A117.41 (13)C66A—C65A—H65A120.00
C12B—O12B—C24B117.35 (12)C64A—C65A—H65A120.00
C16B—O16B—C64B117.60 (15)C65A—C66A—H66A119.00
C2A—N1A—C11A119.14 (13)C61A—C66A—H66A119.00
C2A—N1A—C6A121.23 (12)N1B—C2B—C3B111.14 (12)
C6A—N1A—C11A118.97 (14)N1B—C2B—C21B111.06 (12)
C2B—N1B—C6B120.82 (13)C3B—C2B—C21B110.55 (12)
C2B—N1B—C11B119.48 (12)C2B—C3B—C4B111.18 (13)
C6B—N1B—C11B118.52 (12)C2B—C3B—C31B111.32 (12)
N1A—C2A—C3A111.04 (12)C4B—C3B—C31B112.34 (14)
N1A—C2A—C21A111.08 (13)O4B—C4B—C3B121.78 (15)
C3A—C2A—C21A111.07 (12)O4B—C4B—C5B121.96 (15)
C2A—C3A—C31A110.73 (13)C3B—C4B—C5B116.27 (14)
C4A—C3A—C31A112.49 (14)C4B—C5B—C6B113.58 (12)
C2A—C3A—C4A111.44 (13)N1B—C6B—C5B108.45 (11)
O4A—C4A—C3A122.36 (16)N1B—C6B—C61B111.82 (12)
O4A—C4A—C5A121.66 (16)C5B—C6B—C61B115.96 (13)
C3A—C4A—C5A115.98 (13)O11B—C11B—N1B125.09 (15)
C4A—C5A—C6A113.82 (14)C2B—C21B—C22B120.51 (12)
C5A—C6A—C61A116.35 (12)C2B—C21B—C26B121.05 (13)
N1A—C6A—C61A111.55 (13)C22B—C21B—C26B118.42 (14)
N1A—C6A—C5A107.83 (13)C21B—C22B—C23B121.46 (13)
O11A—C11A—N1A124.69 (15)C22B—C23B—C24B119.09 (14)
C2A—C21A—C26A119.91 (14)O12B—C24B—C23B124.13 (14)
C22A—C21A—C26A118.19 (14)O12B—C24B—C25B115.70 (13)
C2A—C21A—C22A121.89 (13)C23B—C24B—C25B120.16 (15)
C21A—C22A—C23A121.19 (14)C24B—C25B—C26B119.82 (14)
C22A—C23A—C24A119.45 (14)C21B—C26B—C25B121.04 (13)
O12A—C24A—C25A115.65 (14)C6B—C61B—C62B123.48 (14)
O12A—C24A—C23A124.33 (14)C6B—C61B—C66B118.65 (14)
C23A—C24A—C25A120.03 (14)C62B—C61B—C66B117.72 (13)
C24A—C25A—C26A119.60 (14)C61B—C62B—C63B121.82 (15)
C21A—C26A—C25A121.54 (14)C62B—C63B—C64B119.44 (16)
C6A—C61A—C66A118.14 (13)O16B—C64B—C63B124.57 (16)
C62A—C61A—C66A117.57 (14)O16B—C64B—C65B115.81 (16)
C6A—C61A—C62A124.25 (14)C63B—C64B—C65B119.63 (14)
C61A—C62A—C63A121.60 (15)C64B—C65B—C66B120.28 (16)
C62A—C63A—C64A119.71 (14)C61B—C66B—C65B121.11 (16)
O16A—C64A—C65A115.42 (14)N1B—C2B—H2B108.00
O16A—C64A—C63A124.99 (14)C3B—C2B—H2B108.00
C63A—C64A—C65A119.59 (15)C21B—C2B—H2B108.00
C64A—C65A—C66A119.88 (15)C2B—C3B—H3B107.00
C61A—C66A—C65A121.64 (14)C4B—C3B—H3B107.00
C21A—C2A—H2A108.00C31B—C3B—H3B107.00
N1A—C2A—H2A108.00C4B—C5B—H5C109.00
C3A—C2A—H2A108.00C4B—C5B—H5D109.00
C2A—C3A—H3A107.00C6B—C5B—H5C109.00
C4A—C3A—H3A107.00C6B—C5B—H5D109.00
C31A—C3A—H3A107.00H5C—C5B—H5D108.00
C4A—C5A—H5A109.00N1B—C6B—H6B107.00
C6A—C5A—H5B109.00C5B—C6B—H6B107.00
H5A—C5A—H5B108.00C61B—C6B—H6B107.00
C4A—C5A—H5B109.00O11B—C11B—H11B122.3 (12)
C6A—C5A—H5A109.00N1B—C11B—H11B112.6 (12)
N1A—C6A—H6A107.00O12B—C12B—H12D109.00
C61A—C6A—H6A107.00O12B—C12B—H12E109.00
C5A—C6A—H6A107.00O12B—C12B—H12F109.00
O11A—C11A—H11A122.9 (12)H12D—C12B—H12E109.00
N1A—C11A—H11A112.5 (12)H12D—C12B—H12F109.00
O12A—C12A—H12B109.00H12E—C12B—H12F109.00
O12A—C12A—H12C109.00O16B—C16B—H16D109.00
O12A—C12A—H12A109.00O16B—C16B—H16E109.00
H12B—C12A—H12C109.00O16B—C16B—H16F109.00
H12A—C12A—H12B109.00H16D—C16B—H16E109.00
H12A—C12A—H12C109.00H16D—C16B—H16F109.00
O16A—C16A—H16C109.00H16E—C16B—H16F109.00
H16A—C16A—H16B109.00C21B—C22B—H22B119.00
H16A—C16A—H16C109.00C23B—C22B—H22B119.00
H16B—C16A—H16C109.00C22B—C23B—H23B120.00
O16A—C16A—H16A109.00C24B—C23B—H23B120.00
O16A—C16A—H16B109.00C24B—C25B—H25B120.00
C23A—C22A—H22A119.00C26B—C25B—H25B120.00
C21A—C22A—H22A119.00C21B—C26B—H26B119.00
C22A—C23A—H23A120.00C25B—C26B—H26B119.00
C24A—C23A—H23A120.00C3B—C31B—H31D109.00
C26A—C25A—H25A120.00C3B—C31B—H31E109.00
C24A—C25A—H25A120.00C3B—C31B—H31F109.00
C21A—C26A—H26A119.00H31D—C31B—H31E109.00
C25A—C26A—H26A119.00H31D—C31B—H31F109.00
H31B—C31A—H31C109.00H31E—C31B—H31F109.00
C3A—C31A—H31B109.00C61B—C62B—H62B119.00
H31A—C31A—H31C109.00C63B—C62B—H62B119.00
C3A—C31A—H31A109.00C62B—C63B—H63B120.00
C3A—C31A—H31C109.00C64B—C63B—H63B120.00
H31A—C31A—H31B109.00C64B—C65B—H65B120.00
C61A—C62A—H62A119.00C66B—C65B—H65B120.00
C63A—C62A—H62A119.00C61B—C66B—H66B119.00
C62A—C63A—H63A120.00C65B—C66B—H66B119.00
C12A—O12A—C24A—C23A15.1 (2)C22A—C23A—C24A—C25A0.3 (2)
C12A—O12A—C24A—C25A165.35 (15)O12A—C24A—C25A—C26A179.35 (14)
C16A—O16A—C64A—C63A2.8 (3)C23A—C24A—C25A—C26A0.2 (2)
C16A—O16A—C64A—C65A177.15 (16)C24A—C25A—C26A—C21A0.5 (2)
C12B—O12B—C24B—C23B8.3 (2)C66A—C61A—C62A—C63A0.9 (3)
C12B—O12B—C24B—C25B170.39 (16)C6A—C61A—C62A—C63A178.45 (16)
C16B—O16B—C64B—C65B170.52 (15)C6A—C61A—C66A—C65A178.56 (16)
C16B—O16B—C64B—C63B9.3 (2)C62A—C61A—C66A—C65A0.9 (3)
C6A—N1A—C2A—C21A134.29 (13)C61A—C62A—C63A—C64A0.2 (3)
C11A—N1A—C2A—C3A179.22 (13)C62A—C63A—C64A—O16A179.39 (16)
C11A—N1A—C2A—C21A55.10 (18)C62A—C63A—C64A—C65A0.6 (3)
C6A—N1A—C2A—C3A10.16 (19)C63A—C64A—C65A—C66A0.6 (3)
C2A—N1A—C11A—O11A179.34 (15)O16A—C64A—C65A—C66A179.35 (16)
C6A—N1A—C11A—O11A9.8 (2)C64A—C65A—C66A—C61A0.1 (3)
C2A—N1A—C6A—C61A87.54 (17)N1B—C2B—C3B—C4B51.16 (15)
C11A—N1A—C6A—C5A129.24 (15)N1B—C2B—C3B—C31B177.23 (12)
C2A—N1A—C6A—C5A41.39 (18)C21B—C2B—C3B—C4B174.96 (11)
C11A—N1A—C6A—C61A101.83 (16)C21B—C2B—C3B—C31B58.96 (16)
C11B—N1B—C2B—C3B177.91 (13)N1B—C2B—C21B—C22B53.80 (19)
C11B—N1B—C2B—C21B54.40 (17)N1B—C2B—C21B—C26B127.48 (15)
C2B—N1B—C11B—O11B176.20 (14)C3B—C2B—C21B—C22B70.05 (18)
C6B—N1B—C11B—O11B8.5 (2)C3B—C2B—C21B—C26B108.67 (16)
C11B—N1B—C6B—C5B129.69 (14)C2B—C3B—C4B—O4B145.88 (15)
C2B—N1B—C6B—C5B37.80 (17)C2B—C3B—C4B—C5B33.80 (16)
C2B—N1B—C6B—C61B91.30 (15)C31B—C3B—C4B—O4B20.4 (2)
C6B—N1B—C2B—C21B138.23 (13)C31B—C3B—C4B—C5B159.31 (13)
C11B—N1B—C6B—C61B101.21 (15)O4B—C4B—C5B—C6B160.48 (14)
C6B—N1B—C2B—C3B14.71 (17)C3B—C4B—C5B—C6B19.84 (17)
N1A—C2A—C3A—C4A49.92 (17)C4B—C5B—C6B—N1B55.45 (16)
C3A—C2A—C21A—C26A114.74 (16)C4B—C5B—C6B—C61B71.30 (16)
N1A—C2A—C3A—C31A175.94 (13)N1B—C6B—C61B—C62B130.09 (15)
C21A—C2A—C3A—C4A174.06 (13)N1B—C6B—C61B—C66B54.52 (18)
C21A—C2A—C3A—C31A59.92 (17)C5B—C6B—C61B—C62B5.1 (2)
N1A—C2A—C21A—C22A60.01 (18)C5B—C6B—C61B—C66B179.56 (13)
N1A—C2A—C21A—C26A121.16 (15)C2B—C21B—C22B—C23B179.71 (15)
C3A—C2A—C21A—C22A64.10 (19)C26B—C21B—C22B—C23B1.0 (2)
C2A—C3A—C4A—O4A143.90 (16)C2B—C21B—C26B—C25B179.89 (15)
C31A—C3A—C4A—O4A18.9 (2)C22B—C21B—C26B—C25B1.1 (2)
C31A—C3A—C4A—C5A161.50 (13)C21B—C22B—C23B—C24B0.2 (3)
C2A—C3A—C4A—C5A36.46 (19)C22B—C23B—C24B—O12B177.55 (16)
C3A—C4A—C5A—C6A16.50 (19)C22B—C23B—C24B—C25B1.1 (3)
O4A—C4A—C5A—C6A163.15 (15)O12B—C24B—C25B—C26B177.84 (15)
C4A—C5A—C6A—C61A71.46 (19)C23B—C24B—C25B—C26B0.9 (3)
C4A—C5A—C6A—N1A54.69 (16)C24B—C25B—C26B—C21B0.2 (3)
N1A—C6A—C61A—C66A54.5 (2)C6B—C61B—C62B—C63B173.88 (14)
C5A—C6A—C61A—C62A3.7 (2)C66B—C61B—C62B—C63B1.6 (2)
N1A—C6A—C61A—C62A127.93 (17)C6B—C61B—C66B—C65B175.01 (14)
C5A—C6A—C61A—C66A178.79 (16)C62B—C61B—C66B—C65B0.6 (2)
C22A—C21A—C26A—C25A0.3 (2)C61B—C62B—C63B—C64B1.1 (2)
C2A—C21A—C26A—C25A179.15 (14)C62B—C63B—C64B—O16B179.58 (15)
C2A—C21A—C22A—C23A178.60 (14)C62B—C63B—C64B—C65B0.3 (2)
C26A—C21A—C22A—C23A0.3 (2)O16B—C64B—C65B—C66B178.71 (15)
C21A—C22A—C23A—C24A0.5 (2)C63B—C64B—C65B—C66B1.1 (2)
C22A—C23A—C24A—O12A179.82 (15)C64B—C65B—C66B—C61B0.7 (2)
Symmetry codes: (i) x+1, y, z1; (ii) x, y, z+1; (iii) x+1, y+1, z+1; (iv) x, y, z; (v) x+1, y, z+1; (vi) x, y1, z; (vii) x, y+1, z+1; (viii) x+1, y, z; (ix) x+1, y+1, z; (x) x, y+1, z+1; (xi) x, y+1, z; (xii) x1, y, z+1; (xiii) x, y, z+1; (xiv) x, y+1, z; (xv) x, y, z1; (xvi) x, y1, z1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5B···O16Bxiv0.992.473.351 (2)148
C5B—H5C···O11Axv0.992.343.222 (2)148
C12B—H12D···O11Axvi0.982.473.427 (2)167
C16A—H16A···O12Bviii0.982.513.468 (2)167
C16B—H16D···O16Av0.982.473.334 (2)147
C25A—H25A···O4Bxii0.952.433.266 (2)147
C2A—H2A···Cg1vii1.002.713.714 (2)178
C12A—H12B···Cg2ii0.982.923.846 (2)158
Symmetry codes: (ii) x, y, z+1; (v) x+1, y, z+1; (vii) x, y+1, z+1; (viii) x+1, y, z; (xii) x1, y, z+1; (xiv) x, y+1, z; (xv) x, y, z1; (xvi) x, y1, z1.

Experimental details

Crystal data
Chemical formulaC21H23NO4
Mr353.40
Crystal system, space groupTriclinic, P1
Temperature (K)110
a, b, c (Å)11.5409 (4), 12.4972 (5), 14.7816 (6)
α, β, γ (°)67.878 (4), 74.719 (3), 67.123 (4)
V3)1802.42 (14)
Z4
Radiation typeCu Kα
µ (mm1)0.73
Crystal size (mm)0.55 × 0.45 × 0.18
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby Gemini
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.484, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
13170, 7096, 6709
Rint0.020
(sin θ/λ)max1)0.624
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.127, 1.06
No. of reflections7096
No. of parameters477
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.69, 0.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5A—H5B···O16Bi0.992.473.351 (2)148
C5B—H5C···O11Aii0.992.343.222 (2)148
C12B—H12D···O11Aiii0.982.473.427 (2)167
C16A—H16A···O12Biv0.982.513.468 (2)167
C16B—H16D···O16Av0.982.473.334 (2)147
C25A—H25A···O4Bvi0.952.433.266 (2)147
C2A—H2A···Cg1vii1.002.713.714 (2)178
C12A—H12B···Cg2viii0.982.923.846 (2)158
Symmetry codes: (i) x, y+1, z; (ii) x, y, z1; (iii) x, y1, z1; (iv) x+1, y, z; (v) x+1, y, z+1; (vi) x1, y, z+1; (vii) x, y+1, z+1; (viii) x, y, z+1.
 

Acknowledgements

RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.

References

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First citationVenkatraj, M., Ponnuswamy, S. & Jeyaraman, R. (2008). Indian J. Chem. Sect. B, 47, 461–476.  Google Scholar

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