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

Sughanya, V.; Sureshbabu, N.

doi:10.1107/S1600536812036094

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2755

doi:10.1107/S1600536812036094

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

V. Sughanya ^a ^* and N. Sureshbabu ^a

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India
^*Correspondence e-mail: saisukanyashri@gmail.com

(Received 18 July 2012; accepted 16 August 2012; online 23 August 2012)

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.

Related literature

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

Crystal data

C₃₂H₃₇NO₃
M_r = 483.63
Orthorhombic, P b c a
a = 16.8172 (7) Å
b = 15.7033 (7) Å
c = 19.908 (1) Å
V = 5257.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.976, T_max = 0.986
54483 measured reflections
6422 independent reflections
4439 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.128
S = 1.03
6422 reflections
326 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.16 e Å⁻³

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812036094/fy2066sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036094/fy2066Isup2.hkl

checkCIF report

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%).

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

A view of the structure of the title compound showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

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

C₃₂H₃₇NO₃	D_x = 1.222 Mg m⁻³
M_r = 483.63	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 6423 reflections
a = 16.8172 (7) Å	θ = 2.4–27.3°
b = 15.7033 (7) Å	µ = 0.08 mm⁻¹
c = 19.908 (1) Å	T = 296 K
V = 5257.4 (4) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm
F(000) = 2080

Data collection top

Bruker APEXII CCD diffractometer	6422 independent reflections
Radiation source: fine-focus sealed tube	4439 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω and ϕ scan	θ_max = 28.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −22→22
T_min = 0.976, T_max = 0.986	k = −20→20
54483 measured reflections	l = −26→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0534P)² + 1.5474P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6422 reflections	Δρ_max = 0.25 e Å⁻³
326 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0017 (3)

Crystal data top

C₃₂H₃₇NO₃	V = 5257.4 (4) Å³
M_r = 483.63	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.8172 (7) Å	µ = 0.08 mm⁻¹
b = 15.7033 (7) Å	T = 296 K
c = 19.908 (1) Å	0.30 × 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)
T_min = 0.976, T_max = 0.986	R_int = 0.040
54483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.03	Δρ_max = 0.25 e Å⁻³
6422 reflections	Δρ_min = −0.16 e Å⁻³
326 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.43933 (9)	0.70202 (10)	0.33199 (8)	0.0427 (4)
C2	0.44922 (8)	0.61875 (9)	0.29361 (8)	0.0386 (3)
H2A	0.4920	0.6251	0.2613	0.046*
H2B	0.4644	0.5743	0.3249	0.046*
C3	0.37519 (8)	0.59175 (8)	0.25718 (7)	0.0308 (3)
C4	0.31496 (8)	0.64638 (8)	0.24372 (7)	0.0323 (3)
C5	0.32733 (9)	0.73706 (9)	0.25208 (7)	0.0386 (3)
C6	0.40380 (10)	0.76626 (10)	0.28343 (9)	0.0512 (4)
H6A	0.3943	0.8192	0.3072	0.061*
H6B	0.4421	0.7777	0.2481	0.061*
C7	0.38514 (12)	0.68989 (15)	0.39259 (9)	0.0668 (5)
H7A	0.4084	0.6491	0.4227	0.100*
H7B	0.3342	0.6696	0.3779	0.100*
H7C	0.3787	0.7433	0.4154	0.100*
C8	0.52092 (11)	0.73258 (12)	0.35585 (11)	0.0629 (5)
H8A	0.5430	0.6916	0.3863	0.094*
H8B	0.5154	0.7864	0.3783	0.094*
H8C	0.5556	0.7390	0.3179	0.094*
C9	0.23605 (8)	0.61457 (9)	0.21724 (7)	0.0325 (3)
H9	0.2149	0.6583	0.1870	0.039*
C10	0.25047 (8)	0.53568 (9)	0.17623 (7)	0.0329 (3)
C11	0.31540 (8)	0.48656 (8)	0.18523 (6)	0.0307 (3)
C12	0.33256 (8)	0.41003 (9)	0.14247 (7)	0.0362 (3)
H12A	0.3216	0.3592	0.1685	0.043*
H12B	0.3887	0.4097	0.1314	0.043*
C13	0.28452 (9)	0.40604 (10)	0.07704 (7)	0.0418 (4)
C14	0.19796 (9)	0.42652 (11)	0.09332 (8)	0.0462 (4)
H14A	0.1676	0.4279	0.0519	0.055*
H14B	0.1763	0.3816	0.1213	0.055*
C15	0.18853 (8)	0.51014 (10)	0.12889 (7)	0.0382 (3)
C16	0.29115 (11)	0.31582 (12)	0.04862 (10)	0.0615 (5)
H16A	0.2715	0.2758	0.0810	0.092*
H16B	0.3458	0.3034	0.0388	0.092*
H16C	0.2603	0.3117	0.0082	0.092*
C17	0.31637 (12)	0.46944 (13)	0.02556 (8)	0.0594 (5)
H17A	0.3709	0.4563	0.0156	0.089*
H17B	0.3130	0.5261	0.0435	0.089*
H17C	0.2853	0.4659	−0.0148	0.089*
C18	0.42660 (9)	0.44408 (9)	0.26170 (8)	0.0385 (3)
H18A	0.4806	0.4657	0.2601	0.046*
H18B	0.4244	0.3932	0.2341	0.046*
C19	0.40643 (9)	0.42094 (9)	0.33302 (8)	0.0390 (3)
C20	0.32955 (11)	0.39930 (11)	0.35078 (9)	0.0523 (4)
H20	0.2897	0.3994	0.3184	0.063*
C21	0.31140 (15)	0.37766 (14)	0.41603 (11)	0.0765 (6)
H21	0.2596	0.3626	0.4271	0.092*
C22	0.3683 (2)	0.37810 (14)	0.46431 (11)	0.0875 (8)
H22	0.3555	0.3637	0.5083	0.105*
C23	0.4439 (2)	0.39963 (15)	0.44815 (12)	0.0943 (9)
H23	0.4827	0.4008	0.4814	0.113*
C24	0.46399 (13)	0.42012 (12)	0.38220 (11)	0.0687 (6)
H24	0.5164	0.4333	0.3714	0.082*
C25	0.17591 (8)	0.60221 (9)	0.27392 (7)	0.0339 (3)
C26	0.14725 (9)	0.52322 (10)	0.29309 (7)	0.0396 (3)
H26	0.1657	0.4746	0.2715	0.048*
C27	0.09150 (9)	0.51533 (10)	0.34395 (8)	0.0436 (4)
H27	0.0730	0.4616	0.3560	0.052*
C28	0.06319 (9)	0.58640 (11)	0.37696 (8)	0.0428 (4)
C29	0.09195 (9)	0.66542 (11)	0.35946 (9)	0.0500 (4)
H29	0.0743	0.7138	0.3819	0.060*
C30	0.14731 (9)	0.67259 (10)	0.30830 (8)	0.0453 (4)
H30	0.1659	0.7264	0.2966	0.054*
C31	−0.02477 (11)	0.64092 (14)	0.46208 (9)	0.0619 (5)
H31A	0.0179	0.6797	0.4739	0.074*
H31B	−0.0482	0.6201	0.5035	0.074*
C32	−0.08674 (12)	0.68881 (16)	0.42322 (11)	0.0756 (6)
H32A	−0.1065	0.7351	0.4500	0.113*
H32B	−0.1297	0.6511	0.4121	0.113*
H32C	−0.0637	0.7109	0.3827	0.113*
N1	0.37233 (7)	0.50849 (7)	0.23366 (6)	0.0327 (3)
O1	0.12873 (7)	0.55348 (8)	0.12149 (6)	0.0547 (3)
O2	0.27853 (7)	0.78993 (7)	0.23301 (6)	0.0527 (3)
O3	0.00768 (7)	0.57079 (9)	0.42588 (6)	0.0605 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0415 (8)	0.0388 (8)	0.0478 (9)	−0.0022 (6)	−0.0073 (7)	−0.0038 (7)
C2	0.0337 (7)	0.0346 (8)	0.0475 (8)	−0.0009 (6)	−0.0024 (6)	0.0010 (6)
C3	0.0325 (7)	0.0302 (7)	0.0298 (7)	−0.0012 (5)	0.0028 (5)	0.0021 (5)
C4	0.0338 (7)	0.0312 (7)	0.0319 (7)	0.0020 (5)	0.0015 (5)	0.0009 (5)
C5	0.0428 (8)	0.0332 (7)	0.0397 (8)	0.0031 (6)	0.0025 (6)	0.0031 (6)
C6	0.0535 (9)	0.0308 (8)	0.0693 (11)	−0.0031 (7)	−0.0105 (8)	−0.0004 (7)
C7	0.0682 (12)	0.0884 (15)	0.0437 (10)	−0.0004 (11)	−0.0013 (9)	−0.0126 (10)
C8	0.0554 (10)	0.0464 (10)	0.0868 (14)	−0.0040 (8)	−0.0236 (10)	−0.0120 (9)
C9	0.0330 (7)	0.0325 (7)	0.0321 (7)	0.0061 (5)	−0.0010 (5)	−0.0012 (5)
C10	0.0329 (6)	0.0353 (7)	0.0306 (7)	0.0019 (6)	0.0018 (5)	−0.0015 (5)
C11	0.0329 (6)	0.0308 (7)	0.0284 (6)	−0.0001 (5)	0.0044 (5)	0.0009 (5)
C12	0.0344 (7)	0.0354 (8)	0.0389 (7)	0.0024 (6)	0.0055 (6)	−0.0046 (6)
C13	0.0422 (8)	0.0451 (9)	0.0383 (8)	0.0018 (7)	0.0019 (6)	−0.0116 (7)
C14	0.0397 (8)	0.0525 (10)	0.0465 (9)	−0.0004 (7)	−0.0046 (7)	−0.0121 (7)
C15	0.0353 (7)	0.0461 (9)	0.0332 (7)	0.0029 (6)	0.0009 (6)	−0.0022 (6)
C16	0.0597 (11)	0.0598 (11)	0.0650 (12)	0.0051 (9)	−0.0049 (9)	−0.0286 (9)
C17	0.0684 (12)	0.0712 (12)	0.0386 (9)	0.0050 (10)	0.0105 (8)	0.0003 (8)
C18	0.0363 (7)	0.0323 (7)	0.0470 (8)	0.0082 (6)	−0.0030 (6)	−0.0009 (6)
C19	0.0482 (8)	0.0245 (7)	0.0443 (8)	0.0033 (6)	−0.0097 (7)	−0.0009 (6)
C20	0.0543 (10)	0.0492 (10)	0.0534 (10)	0.0019 (8)	−0.0001 (8)	0.0036 (8)
C21	0.0986 (17)	0.0636 (13)	0.0672 (14)	0.0018 (12)	0.0270 (13)	0.0092 (10)
C22	0.162 (3)	0.0540 (13)	0.0459 (11)	−0.0053 (15)	0.0005 (15)	0.0041 (9)
C23	0.152 (3)	0.0677 (15)	0.0630 (14)	−0.0223 (16)	−0.0547 (16)	0.0181 (11)
C24	0.0751 (13)	0.0590 (12)	0.0719 (13)	−0.0124 (10)	−0.0339 (11)	0.0174 (10)
C25	0.0295 (6)	0.0380 (8)	0.0343 (7)	0.0033 (6)	−0.0017 (5)	−0.0050 (6)
C26	0.0416 (8)	0.0384 (8)	0.0390 (8)	0.0066 (6)	0.0021 (6)	−0.0044 (6)
C27	0.0453 (8)	0.0424 (9)	0.0430 (8)	0.0002 (7)	0.0037 (7)	0.0017 (7)
C28	0.0376 (7)	0.0561 (10)	0.0347 (8)	0.0011 (7)	0.0031 (6)	−0.0045 (7)
C29	0.0464 (9)	0.0493 (10)	0.0541 (10)	0.0008 (7)	0.0115 (7)	−0.0199 (8)
C30	0.0431 (8)	0.0383 (8)	0.0545 (9)	−0.0022 (7)	0.0073 (7)	−0.0115 (7)
C31	0.0512 (10)	0.0908 (15)	0.0437 (9)	0.0045 (10)	0.0093 (8)	−0.0171 (9)
C32	0.0558 (11)	0.0931 (16)	0.0777 (14)	0.0088 (11)	0.0036 (10)	−0.0102 (12)
N1	0.0338 (6)	0.0297 (6)	0.0347 (6)	0.0041 (5)	−0.0014 (5)	−0.0003 (5)
O1	0.0443 (6)	0.0648 (8)	0.0551 (7)	0.0161 (6)	−0.0139 (5)	−0.0119 (6)
O2	0.0547 (7)	0.0340 (6)	0.0693 (8)	0.0090 (5)	−0.0071 (6)	0.0060 (5)
O3	0.0585 (7)	0.0716 (9)	0.0515 (7)	0.0025 (6)	0.0200 (6)	−0.0040 (6)

Geometric parameters (Å, º) top

C1—C6	1.520 (2)	C16—H16B	0.9600
C1—C2	1.523 (2)	C16—H16C	0.9600
C1—C7	1.524 (2)	C17—H17A	0.9600
C1—C8	1.529 (2)	C17—H17B	0.9600
C2—C3	1.5020 (19)	C17—H17C	0.9600
C2—H2A	0.9700	C18—N1	1.4723 (17)
C2—H2B	0.9700	C18—C19	1.504 (2)
C3—C4	1.3540 (18)	C18—H18A	0.9700
C3—N1	1.3896 (17)	C18—H18B	0.9700
C4—C5	1.449 (2)	C19—C24	1.377 (2)
C4—C9	1.5127 (19)	C19—C20	1.383 (2)
C5—O2	1.2275 (17)	C20—C21	1.377 (3)
C5—C6	1.501 (2)	C20—H20	0.9300
C6—H6A	0.9700	C21—C22	1.357 (3)
C6—H6B	0.9700	C21—H21	0.9300
C7—H7A	0.9600	C22—C23	1.353 (4)
C7—H7B	0.9600	C22—H22	0.9300
C7—H7C	0.9600	C23—C24	1.394 (3)
C8—H8A	0.9600	C23—H23	0.9300
C8—H8B	0.9600	C24—H24	0.9300
C8—H8C	0.9600	C25—C26	1.384 (2)
C9—C10	1.5033 (19)	C25—C30	1.386 (2)
C9—C25	1.5277 (19)	C26—C27	1.385 (2)
C9—H9	0.9800	C26—H26	0.9300
C10—C11	1.3489 (18)	C27—C28	1.380 (2)
C10—C15	1.4609 (19)	C27—H27	0.9300
C11—N1	1.4017 (17)	C28—O3	1.3711 (19)
C11—C12	1.5007 (18)	C28—C29	1.377 (2)
C12—C13	1.534 (2)	C29—C30	1.384 (2)
C12—H12A	0.9700	C29—H29	0.9300
C12—H12B	0.9700	C30—H30	0.9300
C13—C14	1.526 (2)	C31—O3	1.425 (2)
C13—C17	1.526 (2)	C31—C32	1.500 (3)
C13—C16	1.530 (2)	C31—H31A	0.9700
C14—C15	1.500 (2)	C31—H31B	0.9700
C14—H14A	0.9700	C32—H32A	0.9600
C14—H14B	0.9700	C32—H32B	0.9600
C15—O1	1.2232 (17)	C32—H32C	0.9600
C16—H16A	0.9600

C6—C1—C2	107.08 (13)	C10—C15—C14	118.00 (12)
C6—C1—C7	110.58 (15)	C13—C16—H16A	109.5
C2—C1—C7	110.80 (14)	C13—C16—H16B	109.5
C6—C1—C8	110.00 (14)	H16A—C16—H16B	109.5
C2—C1—C8	109.09 (13)	C13—C16—H16C	109.5
C7—C1—C8	109.26 (15)	H16A—C16—H16C	109.5
C3—C2—C1	113.20 (12)	H16B—C16—H16C	109.5
C3—C2—H2A	108.9	C13—C17—H17A	109.5
C1—C2—H2A	108.9	C13—C17—H17B	109.5
C3—C2—H2B	108.9	H17A—C17—H17B	109.5
C1—C2—H2B	108.9	C13—C17—H17C	109.5
H2A—C2—H2B	107.8	H17A—C17—H17C	109.5
C4—C3—N1	120.23 (12)	H17B—C17—H17C	109.5
C4—C3—C2	122.47 (12)	N1—C18—C19	112.58 (12)
N1—C3—C2	117.19 (11)	N1—C18—H18A	109.1
C3—C4—C5	119.51 (13)	C19—C18—H18A	109.1
C3—C4—C9	121.07 (12)	N1—C18—H18B	109.1
C5—C4—C9	119.37 (12)	C19—C18—H18B	109.1
O2—C5—C4	122.23 (14)	H18A—C18—H18B	107.8
O2—C5—C6	119.65 (13)	C24—C19—C20	118.25 (17)
C4—C5—C6	118.10 (13)	C24—C19—C18	120.99 (16)
C5—C6—C1	113.49 (13)	C20—C19—C18	120.76 (14)
C5—C6—H6A	108.9	C21—C20—C19	120.61 (19)
C1—C6—H6A	108.9	C21—C20—H20	119.7
C5—C6—H6B	108.9	C19—C20—H20	119.7
C1—C6—H6B	108.9	C22—C21—C20	120.7 (2)
H6A—C6—H6B	107.7	C22—C21—H21	119.7
C1—C7—H7A	109.5	C20—C21—H21	119.7
C1—C7—H7B	109.5	C23—C22—C21	119.7 (2)
H7A—C7—H7B	109.5	C23—C22—H22	120.1
C1—C7—H7C	109.5	C21—C22—H22	120.1
H7A—C7—H7C	109.5	C22—C23—C24	120.6 (2)
H7B—C7—H7C	109.5	C22—C23—H23	119.7
C1—C8—H8A	109.5	C24—C23—H23	119.7
C1—C8—H8B	109.5	C19—C24—C23	120.1 (2)
H8A—C8—H8B	109.5	C19—C24—H24	120.0
C1—C8—H8C	109.5	C23—C24—H24	120.0
H8A—C8—H8C	109.5	C26—C25—C30	117.22 (13)
H8B—C8—H8C	109.5	C26—C25—C9	123.23 (12)
C10—C9—C4	108.65 (11)	C30—C25—C9	119.55 (13)
C10—C9—C25	113.78 (12)	C25—C26—C27	121.14 (14)
C4—C9—C25	111.43 (11)	C25—C26—H26	119.4
C10—C9—H9	107.6	C27—C26—H26	119.4
C4—C9—H9	107.6	C28—C27—C26	120.61 (15)
C25—C9—H9	107.6	C28—C27—H27	119.7
C11—C10—C15	120.39 (13)	C26—C27—H27	119.7
C11—C10—C9	121.99 (12)	O3—C28—C29	125.46 (14)
C15—C10—C9	117.48 (12)	O3—C28—C27	115.37 (15)
C10—C11—N1	120.24 (12)	C29—C28—C27	119.16 (14)
C10—C11—C12	122.57 (12)	C28—C29—C30	119.72 (14)
N1—C11—C12	117.11 (11)	C28—C29—H29	120.1
C11—C12—C13	114.40 (12)	C30—C29—H29	120.1
C11—C12—H12A	108.7	C29—C30—C25	122.12 (15)
C13—C12—H12A	108.7	C29—C30—H30	118.9
C11—C12—H12B	108.7	C25—C30—H30	118.9
C13—C12—H12B	108.7	O3—C31—C32	113.12 (16)
H12A—C12—H12B	107.6	O3—C31—H31A	109.0
C14—C13—C17	109.87 (14)	C32—C31—H31A	109.0
C14—C13—C16	110.08 (13)	O3—C31—H31B	109.0
C17—C13—C16	109.29 (14)	C32—C31—H31B	109.0
C14—C13—C12	108.27 (12)	H31A—C31—H31B	107.8
C17—C13—C12	111.03 (13)	C31—C32—H32A	109.5
C16—C13—C12	108.28 (13)	C31—C32—H32B	109.5
C15—C14—C13	112.68 (13)	H32A—C32—H32B	109.5
C15—C14—H14A	109.1	C31—C32—H32C	109.5
C13—C14—H14A	109.1	H32A—C32—H32C	109.5
C15—C14—H14B	109.1	H32B—C32—H32C	109.5
C13—C14—H14B	109.1	C3—N1—C11	119.12 (11)
H14A—C14—H14B	107.8	C3—N1—C18	119.81 (11)
O1—C15—C10	120.74 (13)	C11—N1—C18	121.02 (11)
O1—C15—C14	121.13 (13)	C28—O3—C31	118.81 (15)

C6—C1—C2—C3	−50.29 (17)	C9—C10—C15—C14	−173.31 (13)
C7—C1—C2—C3	70.38 (17)	C13—C14—C15—O1	148.98 (15)
C8—C1—C2—C3	−169.30 (14)	C13—C14—C15—C10	−35.1 (2)
C1—C2—C3—C4	18.00 (19)	N1—C18—C19—C24	−130.50 (16)
C1—C2—C3—N1	−165.83 (12)	N1—C18—C19—C20	49.97 (19)
N1—C3—C4—C5	−163.38 (12)	C24—C19—C20—C21	0.1 (3)
C2—C3—C4—C5	12.7 (2)	C18—C19—C20—C21	179.61 (16)
N1—C3—C4—C9	13.97 (19)	C19—C20—C21—C22	0.8 (3)
C2—C3—C4—C9	−169.97 (12)	C20—C21—C22—C23	−0.3 (4)
C3—C4—C5—O2	170.96 (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—C23	179.12 (18)
C9—C4—C5—C6	175.34 (13)	C22—C23—C24—C19	1.8 (4)
O2—C5—C6—C1	153.19 (15)	C10—C9—C25—C26	10.19 (19)
C4—C5—C6—C1	−28.5 (2)	C4—C9—C25—C26	−113.05 (15)
C2—C1—C6—C5	55.69 (18)	C10—C9—C25—C30	−169.34 (13)
C7—C1—C6—C5	−65.12 (19)	C4—C9—C25—C30	67.41 (17)
C8—C1—C6—C5	174.12 (15)	C30—C25—C26—C27	0.8 (2)
C3—C4—C9—C10	−30.37 (17)	C9—C25—C26—C27	−178.69 (13)
C5—C4—C9—C10	146.99 (13)	C25—C26—C27—C28	−0.1 (2)
C3—C4—C9—C25	95.76 (15)	C26—C27—C28—O3	179.40 (14)
C5—C4—C9—C25	−86.89 (15)	C26—C27—C28—C29	−1.0 (2)
C4—C9—C10—C11	23.49 (18)	O3—C28—C29—C30	−179.07 (15)
C25—C9—C10—C11	−101.26 (15)	C27—C28—C29—C30	1.4 (2)
C4—C9—C10—C15	−160.71 (12)	C28—C29—C30—C25	−0.7 (3)
C25—C9—C10—C15	74.54 (15)	C26—C25—C30—C29	−0.5 (2)
C15—C10—C11—N1	−176.05 (12)	C9—C25—C30—C29	179.10 (14)
C9—C10—C11—N1	−0.4 (2)	C4—C3—N1—C11	12.70 (18)
C15—C10—C11—C12	7.3 (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—C13	15.91 (19)	C2—C3—N1—C18	18.88 (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—C3	157.07 (12)
C11—C12—C13—C17	74.84 (16)	C10—C11—N1—C18	157.81 (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—C3	70.01 (16)
C16—C13—C14—C15	173.24 (14)	C19—C18—N1—C11	−107.50 (14)
C12—C13—C14—C15	55.05 (18)	C29—C28—O3—C31	0.7 (2)
C11—C10—C15—O1	178.49 (14)	C27—C28—O3—C31	−179.71 (14)
C9—C10—C15—O1	2.6 (2)	C32—C31—O3—C28	77.7 (2)
C11—C10—C15—C14	2.6 (2)

Experimental details

Crystal data
Chemical formula	C₃₂H₃₇NO₃
M_r	483.63
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	16.8172 (7), 15.7033 (7), 19.908 (1)
V (Å³)	5257.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.976, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	54483, 6422, 4439
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.663

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.128, 1.03
No. of reflections	6422
No. of parameters	326
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.16

Computer programs: APEX2 (Bruker, 2004), APEX2/SAINT (Bruker, 2004), SAINT/XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002).

Acknowledgements

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

References

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