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Acta Cryst. (2012). E68, o2755    [ doi:10.1107/S1600536812036094 ]

10-Benzyl-9-(4-ethoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

V. Sughanya and N. Sureshbabu

Abstract top

In the title compound, C32H37NO3, the central dihydropyridine ring adopts a nearly planar flattened-boat conformation, whereas both cyclohexenone rings adopt half-chair conformations. The mean and maximum deviations from the mean plane of the dihydropyridine ring are 0.1252 (9) and 0.188 (1) Å, respectively. The 4-ethoxyphenyl and phenyl rings form dihedral angles of 75.20 (4) and 82.14 (5)° with the dihydropyridine mean plane, respectively.

Comment top

Acridine derivatives with a dihydropyridine unit belong to a special class of compounds, because of their wide range of applications in the pharmaceutical and dye industries. They are also well known as therapeutic agents (Wysocka-Skrzela & Ledochowski, 1976; Nasim & Brychcy,1979; Thull & Testa, 1994; Reil et al., 1994; Mandi et al., 1994).

The central dihydropyridine ring is almost planar with a mean deviation from the mean plane of 0.1252 (9) Å and with a maximum deviation of 0.188 (1) Å for C9. The planar 4-ethoxyphenyl and phenyl rings form dihedral angles of 75.20 (4)° and 82.14 (5)° with the dihydropyridine mean plane. The rings A (C1–C6), B (N1/C3/C4/C9/C10/C11) and C (C10–C15) show total puckering amplitudes Q(T) of 0.506 (2) Å, 0.307 (1) Å and 0.470 (2) Å, respectively. The cyclohexenone rings A and C adopt half chair conformation, whereas the central ring B adopts flattened boat conformation. This can be understood from the Cremer & Pople (1975) puckering parameters: φ = = -7.10 (2)° and θ = 62.2 (2)° (for A); φ = 166.5 (2)°, and θ = 77.4 (2)° (for B) and φ = -163.97 (3)°, θ = 56.9 (2)° (for C), respectively. In the title compound, the bond lengths (Allen et al., 1987) and angles are generally within normal ranges. In the dihydropyridine ring C10=C11 and C4=C3 are double bonds (C10—C11 = 1.3489 (18) Å and C4—C3 = 1.3540 (18) Å), as indicated by the bond distances. The C11—C10—C15 [120.39 (13)°] and C3—C4—C5 [119.51 (13)°] angles are almost the same. In this conformation C1 and C13 may be described as flap atoms being away from the plane of the ring. The observed carbonyl bond lengths (C15—O1 = 1.2232 (17) Å and C5—O2 = 1.2275 (17) Å) are also normal.

Related literature top

For general background, see: Wysocka-Skrzela & Ledochowski (1976); Nasim & Brychcy (1979); Thull & Testa (1994); Reil et al. (1994); Mandi et al. (1994). For related structures, see: Abdelhamid et al. (2011); Khalilov et al. (2011); Tang et al. (2008); Tu et al. (2004). For a related synthesis, see: Li et al. (2003). For ring-puckering parameters, see: Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared in two stages. In the first stage, a mixture of 4-ethoxybenzaldehyde (1.2 g, 8 mmol), 5,5-dimethylcyclohexane-1,3-dione (2.24 g, 16 mmol) and 20 ml of ethanol was heated to 70°C for about 10 minutes. The reaction mixture was allowed to cool to room temperature and the resulting solid intermediate, 2,2'-((4-ethoxyphenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) was filtered and dried (m.p.: 411 K, yield: 78%). In the second stage about 0.8 g of this intermediate was dissoloved in 25 ml of acetic acid. The solution was refluxed together with benzylamine (0.33 g, 3 mmol) for 8 h with the reaction being monitored by TLC. After completion of the reaction, the reaction mixture was poured into crushed ice and stirred well. The solid that separated was filtered and dried and then recrystallized from ethanol to yield yellow crystals of the title compound (m.p.: 433 K, yield: 82%).

Refinement top

All the hydrogen atoms were fixed in calculated positions and allowed to ride on their parent atom with d(C—H) = 0.96 Å and Uiso(H) = 1.5 Ueq(C) for CH3, d(C—H) = 0.97 Å and Uiso(H) = 1.2 Ueq(C) for CH2, d(C—H) = 0.98 Å and Uiso(H) = 1.2 Ueq(C) for aliphatic CH and with d(C—H) = 0.93 Å and Uiso(H) = 1.2 Ueq(C) for aromatic CH.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2/SAINT (Bruker, 2004); data reduction: SAINT/XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the structure of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram for the title compound.
10-Benzyl-9-(4-ethoxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10- hexahydroacridine-1,8(2H,5H)-dione top
Crystal data top
C32H37NO3Dx = 1.222 Mg m−3
Mr = 483.63Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 6423 reflections
a = 16.8172 (7) Åθ = 2.4–27.3°
b = 15.7033 (7) ŵ = 0.08 mm−1
c = 19.908 (1) ÅT = 296 K
V = 5257.4 (4) Å3Block, colourless
Z = 80.30 × 0.20 × 0.20 mm
F(000) = 2080
Data collection top
Bruker APEXII CCD
diffractometer		6422 independent reflections
Radiation source: fine-focus sealed tube4439 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω and φ scanθmax = 28.1°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		h = −22→22
Tmin = 0.976, Tmax = 0.986k = −20→20
54483 measured reflectionsl = −26→26
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0534P)2 + 1.5474P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
6422 reflectionsΔρmax = 0.25 e Å−3
326 parametersΔρmin = −0.16 e Å−3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0017 (3)
Crystal data top
C32H37NO3V = 5257.4 (4) Å3
Mr = 483.63Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 16.8172 (7) ŵ = 0.08 mm−1
b = 15.7033 (7) ÅT = 296 K
c = 19.908 (1) Å0.30 × 0.20 × 0.20 mm
Data collection top
Bruker APEXII CCD
diffractometer		6422 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2004)		4439 reflections with I > 2σ(I)
Tmin = 0.976, Tmax = 0.986Rint = 0.040
54483 measured reflectionsθmax = 28.1°
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.128Δρmax = 0.25 e Å−3
S = 1.03Δρmin = −0.16 e Å−3
6422 reflectionsAbsolute structure: ?
326 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C10.43933 (9)0.70202 (10)0.33199 (8)0.0427 (4)
C20.44922 (8)0.61875 (9)0.29361 (8)0.0386 (3)
H2A0.49200.62510.26130.046*
H2B0.46440.57430.32490.046*
C30.37519 (8)0.59175 (8)0.25718 (7)0.0308 (3)
C40.31496 (8)0.64638 (8)0.24372 (7)0.0323 (3)
C50.32733 (9)0.73706 (9)0.25208 (7)0.0386 (3)
C60.40380 (10)0.76626 (10)0.28343 (9)0.0512 (4)
H6A0.39430.81920.30720.061*
H6B0.44210.77770.24810.061*
C70.38514 (12)0.68989 (15)0.39259 (9)0.0668 (5)
H7A0.40840.64910.42270.100*
H7B0.33420.66960.37790.100*
H7C0.37870.74330.41540.100*
C80.52092 (11)0.73258 (12)0.35585 (11)0.0629 (5)
H8A0.54300.69160.38630.094*
H8B0.51540.78640.37830.094*
H8C0.55560.73900.31790.094*
C90.23605 (8)0.61457 (9)0.21724 (7)0.0325 (3)
H90.21490.65830.18700.039*
C100.25047 (8)0.53568 (9)0.17623 (7)0.0329 (3)
C110.31540 (8)0.48656 (8)0.18523 (6)0.0307 (3)
C120.33256 (8)0.41003 (9)0.14247 (7)0.0362 (3)
H12A0.32160.35920.16850.043*
H12B0.38870.40970.13140.043*
C130.28452 (9)0.40604 (10)0.07704 (7)0.0418 (4)
C140.19796 (9)0.42652 (11)0.09332 (8)0.0462 (4)
H14A0.16760.42790.05190.055*
H14B0.17630.38160.12130.055*
C150.18853 (8)0.51014 (10)0.12889 (7)0.0382 (3)
C160.29115 (11)0.31582 (12)0.04862 (10)0.0615 (5)
H16A0.27150.27580.08100.092*
H16B0.34580.30340.03880.092*
H16C0.26030.31170.00820.092*
C170.31637 (12)0.46944 (13)0.02556 (8)0.0594 (5)
H17A0.37090.45630.01560.089*
H17B0.31300.52610.04350.089*
H17C0.28530.4659−0.01480.089*
C180.42660 (9)0.44408 (9)0.26170 (8)0.0385 (3)
H18A0.48060.46570.26010.046*
H18B0.42440.39320.23410.046*
C190.40643 (9)0.42094 (9)0.33302 (8)0.0390 (3)
C200.32955 (11)0.39930 (11)0.35078 (9)0.0523 (4)
H200.28970.39940.31840.063*
C210.31140 (15)0.37766 (14)0.41603 (11)0.0765 (6)
H210.25960.36260.42710.092*
C220.3683 (2)0.37810 (14)0.46431 (11)0.0875 (8)
H220.35550.36370.50830.105*
C230.4439 (2)0.39963 (15)0.44815 (12)0.0943 (9)
H230.48270.40080.48140.113*
C240.46399 (13)0.42012 (12)0.38220 (11)0.0687 (6)
H240.51640.43330.37140.082*
C250.17591 (8)0.60221 (9)0.27392 (7)0.0339 (3)
C260.14725 (9)0.52322 (10)0.29309 (7)0.0396 (3)
H260.16570.47460.27150.048*
C270.09150 (9)0.51533 (10)0.34395 (8)0.0436 (4)
H270.07300.46160.35600.052*
C280.06319 (9)0.58640 (11)0.37696 (8)0.0428 (4)
C290.09195 (9)0.66542 (11)0.35946 (9)0.0500 (4)
H290.07430.71380.38190.060*
C300.14731 (9)0.67259 (10)0.30830 (8)0.0453 (4)
H300.16590.72640.29660.054*
C31−0.02477 (11)0.64092 (14)0.46208 (9)0.0619 (5)
H31A0.01790.67970.47390.074*
H31B−0.04820.62010.50350.074*
C32−0.08674 (12)0.68881 (16)0.42322 (11)0.0756 (6)
H32A−0.10650.73510.45000.113*
H32B−0.12970.65110.41210.113*
H32C−0.06370.71090.38270.113*
N10.37233 (7)0.50849 (7)0.23366 (6)0.0327 (3)
O10.12873 (7)0.55348 (8)0.12149 (6)0.0547 (3)
O20.27853 (7)0.78993 (7)0.23301 (6)0.0527 (3)
O30.00768 (7)0.57079 (9)0.42588 (6)0.0605 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0415 (8)0.0388 (8)0.0478 (9)−0.0022 (6)−0.0073 (7)−0.0038 (7)
C20.0337 (7)0.0346 (8)0.0475 (8)−0.0009 (6)−0.0024 (6)0.0010 (6)
C30.0325 (7)0.0302 (7)0.0298 (7)−0.0012 (5)0.0028 (5)0.0021 (5)
C40.0338 (7)0.0312 (7)0.0319 (7)0.0020 (5)0.0015 (5)0.0009 (5)
C50.0428 (8)0.0332 (7)0.0397 (8)0.0031 (6)0.0025 (6)0.0031 (6)
C60.0535 (9)0.0308 (8)0.0693 (11)−0.0031 (7)−0.0105 (8)−0.0004 (7)
C70.0682 (12)0.0884 (15)0.0437 (10)−0.0004 (11)−0.0013 (9)−0.0126 (10)
C80.0554 (10)0.0464 (10)0.0868 (14)−0.0040 (8)−0.0236 (10)−0.0120 (9)
C90.0330 (7)0.0325 (7)0.0321 (7)0.0061 (5)−0.0010 (5)−0.0012 (5)
C100.0329 (6)0.0353 (7)0.0306 (7)0.0019 (6)0.0018 (5)−0.0015 (5)
C110.0329 (6)0.0308 (7)0.0284 (6)−0.0001 (5)0.0044 (5)0.0009 (5)
C120.0344 (7)0.0354 (8)0.0389 (7)0.0024 (6)0.0055 (6)−0.0046 (6)
C130.0422 (8)0.0451 (9)0.0383 (8)0.0018 (7)0.0019 (6)−0.0116 (7)
C140.0397 (8)0.0525 (10)0.0465 (9)−0.0004 (7)−0.0046 (7)−0.0121 (7)
C150.0353 (7)0.0461 (9)0.0332 (7)0.0029 (6)0.0009 (6)−0.0022 (6)
C160.0597 (11)0.0598 (11)0.0650 (12)0.0051 (9)−0.0049 (9)−0.0286 (9)
C170.0684 (12)0.0712 (12)0.0386 (9)0.0050 (10)0.0105 (8)0.0003 (8)
C180.0363 (7)0.0323 (7)0.0470 (8)0.0082 (6)−0.0030 (6)−0.0009 (6)
C190.0482 (8)0.0245 (7)0.0443 (8)0.0033 (6)−0.0097 (7)−0.0009 (6)
C200.0543 (10)0.0492 (10)0.0534 (10)0.0019 (8)−0.0001 (8)0.0036 (8)
C210.0986 (17)0.0636 (13)0.0672 (14)0.0018 (12)0.0270 (13)0.0092 (10)
C220.162 (3)0.0540 (13)0.0459 (11)−0.0053 (15)0.0005 (15)0.0041 (9)
C230.152 (3)0.0677 (15)0.0630 (14)−0.0223 (16)−0.0547 (16)0.0181 (11)
C240.0751 (13)0.0590 (12)0.0719 (13)−0.0124 (10)−0.0339 (11)0.0174 (10)
C250.0295 (6)0.0380 (8)0.0343 (7)0.0033 (6)−0.0017 (5)−0.0050 (6)
C260.0416 (8)0.0384 (8)0.0390 (8)0.0066 (6)0.0021 (6)−0.0044 (6)
C270.0453 (8)0.0424 (9)0.0430 (8)0.0002 (7)0.0037 (7)0.0017 (7)
C280.0376 (7)0.0561 (10)0.0347 (8)0.0011 (7)0.0031 (6)−0.0045 (7)
C290.0464 (9)0.0493 (10)0.0541 (10)0.0008 (7)0.0115 (7)−0.0199 (8)
C300.0431 (8)0.0383 (8)0.0545 (9)−0.0022 (7)0.0073 (7)−0.0115 (7)
C310.0512 (10)0.0908 (15)0.0437 (9)0.0045 (10)0.0093 (8)−0.0171 (9)
C320.0558 (11)0.0931 (16)0.0777 (14)0.0088 (11)0.0036 (10)−0.0102 (12)
N10.0338 (6)0.0297 (6)0.0347 (6)0.0041 (5)−0.0014 (5)−0.0003 (5)
O10.0443 (6)0.0648 (8)0.0551 (7)0.0161 (6)−0.0139 (5)−0.0119 (6)
O20.0547 (7)0.0340 (6)0.0693 (8)0.0090 (5)−0.0071 (6)0.0060 (5)
O30.0585 (7)0.0716 (9)0.0515 (7)0.0025 (6)0.0200 (6)−0.0040 (6)
Geometric parameters (Å, º) top
C1—C61.520 (2)C16—H16B0.9600
C1—C21.523 (2)C16—H16C0.9600
C1—C71.524 (2)C17—H17A0.9600
C1—C81.529 (2)C17—H17B0.9600
C2—C31.5020 (19)C17—H17C0.9600
C2—H2A0.9700C18—N11.4723 (17)
C2—H2B0.9700C18—C191.504 (2)
C3—C41.3540 (18)C18—H18A0.9700
C3—N11.3896 (17)C18—H18B0.9700
C4—C51.449 (2)C19—C241.377 (2)
C4—C91.5127 (19)C19—C201.383 (2)
C5—O21.2275 (17)C20—C211.377 (3)
C5—C61.501 (2)C20—H200.9300
C6—H6A0.9700C21—C221.357 (3)
C6—H6B0.9700C21—H210.9300
C7—H7A0.9600C22—C231.353 (4)
C7—H7B0.9600C22—H220.9300
C7—H7C0.9600C23—C241.394 (3)
C8—H8A0.9600C23—H230.9300
C8—H8B0.9600C24—H240.9300
C8—H8C0.9600C25—C261.384 (2)
C9—C101.5033 (19)C25—C301.386 (2)
C9—C251.5277 (19)C26—C271.385 (2)
C9—H90.9800C26—H260.9300
C10—C111.3489 (18)C27—C281.380 (2)
C10—C151.4609 (19)C27—H270.9300
C11—N11.4017 (17)C28—O31.3711 (19)
C11—C121.5007 (18)C28—C291.377 (2)
C12—C131.534 (2)C29—C301.384 (2)
C12—H12A0.9700C29—H290.9300
C12—H12B0.9700C30—H300.9300
C13—C141.526 (2)C31—O31.425 (2)
C13—C171.526 (2)C31—C321.500 (3)
C13—C161.530 (2)C31—H31A0.9700
C14—C151.500 (2)C31—H31B0.9700
C14—H14A0.9700C32—H32A0.9600
C14—H14B0.9700C32—H32B0.9600
C15—O11.2232 (17)C32—H32C0.9600
C16—H16A0.9600
C6—C1—C2107.08 (13)C10—C15—C14118.00 (12)
C6—C1—C7110.58 (15)C13—C16—H16A109.5
C2—C1—C7110.80 (14)C13—C16—H16B109.5
C6—C1—C8110.00 (14)H16A—C16—H16B109.5
C2—C1—C8109.09 (13)C13—C16—H16C109.5
C7—C1—C8109.26 (15)H16A—C16—H16C109.5
C3—C2—C1113.20 (12)H16B—C16—H16C109.5
C3—C2—H2A108.9C13—C17—H17A109.5
C1—C2—H2A108.9C13—C17—H17B109.5
C3—C2—H2B108.9H17A—C17—H17B109.5
C1—C2—H2B108.9C13—C17—H17C109.5
H2A—C2—H2B107.8H17A—C17—H17C109.5
C4—C3—N1120.23 (12)H17B—C17—H17C109.5
C4—C3—C2122.47 (12)N1—C18—C19112.58 (12)
N1—C3—C2117.19 (11)N1—C18—H18A109.1
C3—C4—C5119.51 (13)C19—C18—H18A109.1
C3—C4—C9121.07 (12)N1—C18—H18B109.1
C5—C4—C9119.37 (12)C19—C18—H18B109.1
O2—C5—C4122.23 (14)H18A—C18—H18B107.8
O2—C5—C6119.65 (13)C24—C19—C20118.25 (17)
C4—C5—C6118.10 (13)C24—C19—C18120.99 (16)
C5—C6—C1113.49 (13)C20—C19—C18120.76 (14)
C5—C6—H6A108.9C21—C20—C19120.61 (19)
C1—C6—H6A108.9C21—C20—H20119.7
C5—C6—H6B108.9C19—C20—H20119.7
C1—C6—H6B108.9C22—C21—C20120.7 (2)
H6A—C6—H6B107.7C22—C21—H21119.7
C1—C7—H7A109.5C20—C21—H21119.7
C1—C7—H7B109.5C23—C22—C21119.7 (2)
H7A—C7—H7B109.5C23—C22—H22120.1
C1—C7—H7C109.5C21—C22—H22120.1
H7A—C7—H7C109.5C22—C23—C24120.6 (2)
H7B—C7—H7C109.5C22—C23—H23119.7
C1—C8—H8A109.5C24—C23—H23119.7
C1—C8—H8B109.5C19—C24—C23120.1 (2)
H8A—C8—H8B109.5C19—C24—H24120.0
C1—C8—H8C109.5C23—C24—H24120.0
H8A—C8—H8C109.5C26—C25—C30117.22 (13)
H8B—C8—H8C109.5C26—C25—C9123.23 (12)
C10—C9—C4108.65 (11)C30—C25—C9119.55 (13)
C10—C9—C25113.78 (12)C25—C26—C27121.14 (14)
C4—C9—C25111.43 (11)C25—C26—H26119.4
C10—C9—H9107.6C27—C26—H26119.4
C4—C9—H9107.6C28—C27—C26120.61 (15)
C25—C9—H9107.6C28—C27—H27119.7
C11—C10—C15120.39 (13)C26—C27—H27119.7
C11—C10—C9121.99 (12)O3—C28—C29125.46 (14)
C15—C10—C9117.48 (12)O3—C28—C27115.37 (15)
C10—C11—N1120.24 (12)C29—C28—C27119.16 (14)
C10—C11—C12122.57 (12)C28—C29—C30119.72 (14)
N1—C11—C12117.11 (11)C28—C29—H29120.1
C11—C12—C13114.40 (12)C30—C29—H29120.1
C11—C12—H12A108.7C29—C30—C25122.12 (15)
C13—C12—H12A108.7C29—C30—H30118.9
C11—C12—H12B108.7C25—C30—H30118.9
C13—C12—H12B108.7O3—C31—C32113.12 (16)
H12A—C12—H12B107.6O3—C31—H31A109.0
C14—C13—C17109.87 (14)C32—C31—H31A109.0
C14—C13—C16110.08 (13)O3—C31—H31B109.0
C17—C13—C16109.29 (14)C32—C31—H31B109.0
C14—C13—C12108.27 (12)H31A—C31—H31B107.8
C17—C13—C12111.03 (13)C31—C32—H32A109.5
C16—C13—C12108.28 (13)C31—C32—H32B109.5
C15—C14—C13112.68 (13)H32A—C32—H32B109.5
C15—C14—H14A109.1C31—C32—H32C109.5
C13—C14—H14A109.1H32A—C32—H32C109.5
C15—C14—H14B109.1H32B—C32—H32C109.5
C13—C14—H14B109.1C3—N1—C11119.12 (11)
H14A—C14—H14B107.8C3—N1—C18119.81 (11)
O1—C15—C10120.74 (13)C11—N1—C18121.02 (11)
O1—C15—C14121.13 (13)C28—O3—C31118.81 (15)
C6—C1—C2—C3−50.29 (17)C9—C10—C15—C14−173.31 (13)
C7—C1—C2—C370.38 (17)C13—C14—C15—O1148.98 (15)
C8—C1—C2—C3−169.30 (14)C13—C14—C15—C10−35.1 (2)
C1—C2—C3—C418.00 (19)N1—C18—C19—C24−130.50 (16)
C1—C2—C3—N1−165.83 (12)N1—C18—C19—C2049.97 (19)
N1—C3—C4—C5−163.38 (12)C24—C19—C20—C210.1 (3)
C2—C3—C4—C512.7 (2)C18—C19—C20—C21179.61 (16)
N1—C3—C4—C913.97 (19)C19—C20—C21—C220.8 (3)
C2—C3—C4—C9−169.97 (12)C20—C21—C22—C23−0.3 (4)
C3—C4—C5—O2170.96 (14)C21—C22—C23—C24−1.0 (4)
C9—C4—C5—O2−6.4 (2)C20—C19—C24—C23−1.3 (3)
C3—C4—C5—C6−7.3 (2)C18—C19—C24—C23179.12 (18)
C9—C4—C5—C6175.34 (13)C22—C23—C24—C191.8 (4)
O2—C5—C6—C1153.19 (15)C10—C9—C25—C2610.19 (19)
C4—C5—C6—C1−28.5 (2)C4—C9—C25—C26−113.05 (15)
C2—C1—C6—C555.69 (18)C10—C9—C25—C30−169.34 (13)
C7—C1—C6—C5−65.12 (19)C4—C9—C25—C3067.41 (17)
C8—C1—C6—C5174.12 (15)C30—C25—C26—C270.8 (2)
C3—C4—C9—C10−30.37 (17)C9—C25—C26—C27−178.69 (13)
C5—C4—C9—C10146.99 (13)C25—C26—C27—C28−0.1 (2)
C3—C4—C9—C2595.76 (15)C26—C27—C28—O3179.40 (14)
C5—C4—C9—C25−86.89 (15)C26—C27—C28—C29−1.0 (2)
C4—C9—C10—C1123.49 (18)O3—C28—C29—C30−179.07 (15)
C25—C9—C10—C11−101.26 (15)C27—C28—C29—C301.4 (2)
C4—C9—C10—C15−160.71 (12)C28—C29—C30—C25−0.7 (3)
C25—C9—C10—C1574.54 (15)C26—C25—C30—C29−0.5 (2)
C15—C10—C11—N1−176.05 (12)C9—C25—C30—C29179.10 (14)
C9—C10—C11—N1−0.4 (2)C4—C3—N1—C1112.70 (18)
C15—C10—C11—C127.3 (2)C2—C3—N1—C11−163.56 (12)
C9—C10—C11—C12−176.98 (12)C4—C3—N1—C18−164.86 (12)
C10—C11—C12—C1315.91 (19)C2—C3—N1—C1818.88 (18)
N1—C11—C12—C13−160.80 (12)C10—C11—N1—C3−19.72 (18)
C11—C12—C13—C14−45.85 (17)C12—C11—N1—C3157.07 (12)
C11—C12—C13—C1774.84 (16)C10—C11—N1—C18157.81 (13)
C11—C12—C13—C16−165.18 (13)C12—C11—N1—C18−25.40 (18)
C17—C13—C14—C15−66.36 (17)C19—C18—N1—C370.01 (16)
C16—C13—C14—C15173.24 (14)C19—C18—N1—C11−107.50 (14)
C12—C13—C14—C1555.05 (18)C29—C28—O3—C310.7 (2)
C11—C10—C15—O1178.49 (14)C27—C28—O3—C31−179.71 (14)
C9—C10—C15—O12.6 (2)C32—C31—O3—C2877.7 (2)
C11—C10—C15—C142.6 (2)
Acknowledgements top

The authors thank Dr Babu Varghese and SAIF, IIT Madras, for intensity data collection.

references
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