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The title compound, C36H33N3O2, was synthesized by the intermolecular [3 + 2]-cyclo­addition of azomethine yl­ide, derived from isatin and sarcosine by a de­carboxyl­ative route, and 1-benzyl-3,5-di­benzyl­idene-piperidin-4-one. There are two ­spiro junctions in the mol­ecule, which consists of a nearly planar 2-ox­indole ring, an envelope pyrrolidine ring and a chair piperidone ring. There is an intermolecular N—H...O hydrogen bond, the N...O distance being 2.835 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803008985/ob6240sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803008985/ob6240Isup2.hkl
Contains datablock I

CCDC reference: 214637

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.063
  • wR factor = 0.181
  • Data-to-parameter ratio = 13.8

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are important processes for the construction of spiro compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I), is reported.

There are dispiro rings in the molecule which consists of 2-oxindole, pyrrolidine and piperidone rings. The pyrrolidine ring (N2/C7/C6/C5/C8) is not planar, but shows an envelope conformation. The N2/C8/C5/C6 moiety is nearly planar and the mean deviation from this plane is 0.03 (1) Å. Atom C7 is shifted from the N2/C8/C5/C6 plane by 0.64 (2) Å. The dihedral angle between the N2/C7/C6 and N2/C8/C5/C6 planes is 43.4 (4)°. The dihedral angle between the C30—C36 phenyl plane and the N2/C8/C5/C6 plane is 63.9 (3)°. The 2-oxindole ring (C8/C9/N3/C10/C15/C14/C13/C12/C11) is nearly planar and the mean deviation from this plane is 0.03 (1) Å. The dihedral angle between the 2-oxindole ring mean plane and the N2/C8/C5/C6 plane is 86.9 (3)°. The piperidone ring has the usual chair conformation. In the crystal structure, there are intermolecular N—H···O hydrogen bonds (Fig. 2 and Table 2).

Experimental top

A mixture of 1-benzyl-3,5-dibenzylidene-piperidin-4-one (2 mmol), isatin (2 mmol) and sarcosine (2 mmol) were refluxed in methanol (80 ml) until the disapperence of the starting material as evidenced by the thin-layer chromatography. After the reaction was complete, the solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 5:1) to give the title compound, (I). 20 mg of (I) was dissolved in 15 ml chloroform, the solution was kept at room temperature for 15 d by natural evaporation to give colorless single crystals of (I), suitable for X-ray analysis. M.p. 487–488 K; IR (KBr, cm−1): 3493 (N—H), 1694, 1682 (CO); 1H NMR (CDCl3, p.p.m.): 1.86 (1H, d), 2.16 (3H, s), 2.76–2.81 (1H, m), 3.18 (1H, d), 3.41 (2H, m), 3.42–3.64 (1H, m), 3.93 (1H, d), 3.94–4.00 (1H, m), 4.80–4.86 (1H, m), 6.67 (1H, s), 6.67–7.37 (19H, m); 7.40 (1H, br).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
[Figure 2] Fig. 2. The crystal structure of (I), viewed along a axis. The broken lines indicate hydrogen bonds.
1''-Benzyl-5''-benzylidene-1'-methyl-4'-phenyl-1H-indole-3-spiro-2'- pyrrolidine-3'-spiro-3''-piperidine-2(3H),3''-dione top
Crystal data top
C36H33N3O2Z = 2
Mr = 539.65F(000) = 572
Triclinic, P1Dx = 1.222 Mg m3
a = 8.535 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.441 (4) ÅCell parameters from 715 reflections
c = 15.682 (6) Åθ = 2.5–25.5°
α = 102.027 (7)°µ = 0.08 mm1
β = 92.423 (7)°T = 293 K
γ = 100.637 (7)°Plate, colorless
V = 1466.8 (10) Å30.22 × 0.16 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2883 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 25.0°, θmin = 1.3°
ϕ and ω scansh = 1010
7663 measured reflectionsk = 138
5152 independent reflectionsl = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.063 w = 1/[σ2(Fo2) + (0.084P)2P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.181(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.30 e Å3
5152 reflectionsΔρmin = 0.25 e Å3
372 parameters
Crystal data top
C36H33N3O2γ = 100.637 (7)°
Mr = 539.65V = 1466.8 (10) Å3
Triclinic, P1Z = 2
a = 8.535 (3) ÅMo Kα radiation
b = 11.441 (4) ŵ = 0.08 mm1
c = 15.682 (6) ÅT = 293 K
α = 102.027 (7)°0.22 × 0.16 × 0.08 mm
β = 92.423 (7)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2883 reflections with I > 2σ(I)
7663 measured reflectionsRint = 0.030
5152 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.181H-atom parameters constrained
S = 1.10Δρmax = 0.30 e Å3
5152 reflectionsΔρmin = 0.25 e Å3
372 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.3290 (3)0.5441 (2)0.19416 (15)0.0464 (7)
N20.0016 (3)0.7926 (3)0.22094 (17)0.0584 (8)
N30.0354 (3)0.4988 (2)0.10941 (15)0.0521 (7)
H3A0.05420.44520.06090.062*
O10.1237 (3)0.6503 (2)0.06047 (13)0.0611 (7)
O20.2191 (3)0.7492 (2)0.41867 (13)0.0623 (7)
C10.3621 (4)0.6767 (3)0.20849 (19)0.0472 (8)
H1A0.36010.70060.15270.057*
H1B0.46770.70950.23860.057*
C20.3736 (4)0.5101 (3)0.27590 (19)0.0518 (8)
H2A0.48660.54170.29290.062*
H2B0.35460.42200.26710.062*
C30.2772 (4)0.5607 (3)0.34652 (18)0.0455 (8)
C40.2428 (3)0.6845 (3)0.35056 (19)0.0469 (8)
C50.2364 (4)0.7276 (3)0.26335 (18)0.0447 (8)
C60.2577 (4)0.8684 (3)0.2798 (2)0.0524 (9)
H60.22270.89540.33810.063*
C70.1325 (4)0.8871 (3)0.2147 (2)0.0655 (10)
H7A0.10680.96750.23140.079*
H7B0.16760.87590.15600.079*
C80.0597 (4)0.6802 (3)0.21619 (18)0.0481 (8)
C90.0591 (4)0.6091 (3)0.11943 (19)0.0485 (8)
C100.1000 (4)0.4817 (3)0.18775 (18)0.0468 (8)
C110.0524 (4)0.5884 (3)0.25167 (18)0.0469 (8)
C120.1153 (4)0.5948 (4)0.33169 (19)0.0569 (9)
H120.09100.66680.37430.068*
C130.2137 (4)0.4943 (4)0.3479 (2)0.0634 (10)
H130.25500.49860.40220.076*
C140.2526 (4)0.3871 (4)0.2856 (2)0.0634 (10)
H140.31550.31890.29900.076*
C150.1985 (4)0.3802 (3)0.2029 (2)0.0583 (9)
H150.22780.30940.15930.070*
C160.4123 (4)0.4874 (3)0.1216 (2)0.0606 (10)
H16A0.52620.50620.13890.073*
H16B0.39560.52330.07190.073*
C170.3591 (5)0.3507 (3)0.0931 (2)0.0588 (9)
C180.4556 (5)0.2844 (4)0.0435 (2)0.0753 (12)
H180.55370.32390.03000.090*
C190.4078 (7)0.1594 (4)0.0135 (3)0.0939 (15)
H190.47380.11570.02020.113*
C200.2637 (9)0.0996 (5)0.0332 (3)0.1075 (18)
H200.23180.01580.01290.129*
C210.1685 (7)0.1637 (4)0.0823 (3)0.0947 (15)
H210.07150.12330.09630.114*
C220.2140 (5)0.2892 (4)0.1120 (3)0.0740 (11)
H220.14640.33220.14490.089*
C230.2149 (4)0.5008 (3)0.40564 (19)0.0517 (9)
H230.15140.54030.44410.062*
C240.2343 (4)0.3802 (3)0.41726 (19)0.0505 (9)
C250.3816 (5)0.3487 (4)0.4197 (2)0.0659 (10)
H250.47060.40340.41010.079*
C260.4014 (5)0.2397 (4)0.4358 (3)0.0808 (12)
H260.50310.22140.43750.097*
C270.2733 (6)0.1573 (4)0.4496 (3)0.0809 (12)
H270.28670.08220.45940.097*
C280.1244 (6)0.1863 (4)0.4490 (3)0.0809 (13)
H280.03650.13090.45900.097*
C290.1045 (5)0.2974 (4)0.4335 (2)0.0699 (11)
H290.00340.31680.43400.084*
C300.4274 (4)0.9372 (3)0.2810 (2)0.0567 (9)
C310.5353 (5)0.9460 (4)0.3505 (3)0.0837 (13)
H310.50320.90860.39590.100*
C320.6903 (5)1.0092 (4)0.3544 (3)0.0987 (15)
H320.76181.01290.40170.118*
C330.7394 (5)1.0662 (4)0.2892 (3)0.0891 (14)
H330.84341.10990.29200.107*
C340.6337 (6)1.0579 (4)0.2206 (3)0.0923 (15)
H340.66611.09550.17530.111*
C350.4790 (5)0.9948 (3)0.2166 (2)0.0744 (12)
H350.40820.99140.16900.089*
C360.1439 (5)0.7821 (4)0.1619 (3)0.0804 (12)
H36A0.18140.85750.17350.121*
H36B0.22640.71760.17110.121*
H36C0.11720.76420.10230.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0580 (16)0.0462 (16)0.0383 (14)0.0167 (14)0.0087 (12)0.0098 (12)
N20.0595 (18)0.0513 (18)0.0610 (17)0.0175 (16)0.0123 (14)0.0024 (14)
N30.0659 (18)0.0519 (18)0.0319 (14)0.0055 (15)0.0017 (12)0.0010 (12)
O10.0765 (16)0.0631 (15)0.0368 (12)0.0011 (13)0.0012 (11)0.0101 (11)
O20.0771 (16)0.0704 (16)0.0369 (12)0.0244 (14)0.0015 (11)0.0019 (11)
C10.0524 (19)0.049 (2)0.0395 (16)0.0098 (17)0.0026 (14)0.0089 (14)
C20.056 (2)0.059 (2)0.0472 (18)0.0217 (18)0.0098 (15)0.0163 (16)
C30.0463 (18)0.054 (2)0.0364 (16)0.0154 (16)0.0010 (14)0.0078 (15)
C40.0426 (18)0.058 (2)0.0374 (17)0.0119 (17)0.0011 (14)0.0029 (16)
C50.0510 (19)0.0461 (19)0.0358 (16)0.0117 (16)0.0013 (14)0.0052 (14)
C60.065 (2)0.045 (2)0.0421 (17)0.0117 (18)0.0049 (15)0.0001 (15)
C70.083 (3)0.048 (2)0.065 (2)0.021 (2)0.0129 (19)0.0061 (17)
C80.057 (2)0.0458 (19)0.0371 (16)0.0109 (17)0.0064 (14)0.0004 (14)
C90.054 (2)0.052 (2)0.0361 (17)0.0082 (18)0.0031 (15)0.0055 (15)
C100.0498 (19)0.053 (2)0.0377 (16)0.0130 (17)0.0002 (14)0.0097 (15)
C110.0449 (18)0.058 (2)0.0366 (16)0.0154 (16)0.0011 (14)0.0032 (15)
C120.0481 (19)0.080 (3)0.0396 (18)0.019 (2)0.0003 (15)0.0008 (17)
C130.047 (2)0.099 (3)0.047 (2)0.016 (2)0.0077 (16)0.020 (2)
C140.056 (2)0.077 (3)0.061 (2)0.011 (2)0.0089 (18)0.024 (2)
C150.061 (2)0.053 (2)0.059 (2)0.0101 (19)0.0026 (17)0.0087 (17)
C160.074 (2)0.059 (2)0.053 (2)0.020 (2)0.0185 (18)0.0120 (17)
C170.084 (3)0.058 (2)0.0394 (18)0.027 (2)0.0015 (17)0.0109 (16)
C180.112 (3)0.077 (3)0.046 (2)0.049 (3)0.004 (2)0.008 (2)
C190.151 (5)0.077 (3)0.061 (3)0.065 (3)0.003 (3)0.003 (2)
C200.167 (6)0.063 (3)0.091 (4)0.039 (4)0.029 (4)0.007 (3)
C210.119 (4)0.060 (3)0.101 (4)0.010 (3)0.020 (3)0.020 (3)
C220.089 (3)0.058 (3)0.076 (3)0.019 (2)0.002 (2)0.015 (2)
C230.054 (2)0.064 (2)0.0394 (17)0.0189 (18)0.0056 (15)0.0097 (16)
C240.055 (2)0.059 (2)0.0394 (17)0.0129 (19)0.0093 (15)0.0118 (15)
C250.065 (2)0.072 (3)0.072 (2)0.019 (2)0.0164 (19)0.033 (2)
C260.083 (3)0.087 (3)0.090 (3)0.036 (3)0.019 (2)0.040 (3)
C270.111 (4)0.064 (3)0.071 (3)0.020 (3)0.004 (2)0.019 (2)
C280.089 (3)0.066 (3)0.079 (3)0.013 (3)0.002 (2)0.020 (2)
C290.061 (2)0.079 (3)0.065 (2)0.003 (2)0.0015 (18)0.018 (2)
C300.073 (2)0.0384 (19)0.053 (2)0.0081 (18)0.0017 (18)0.0008 (16)
C310.072 (3)0.092 (3)0.077 (3)0.013 (3)0.021 (2)0.027 (2)
C320.078 (3)0.103 (4)0.106 (4)0.006 (3)0.022 (3)0.029 (3)
C330.078 (3)0.066 (3)0.107 (4)0.012 (2)0.001 (3)0.007 (3)
C340.114 (4)0.069 (3)0.082 (3)0.011 (3)0.009 (3)0.017 (2)
C350.092 (3)0.056 (2)0.064 (2)0.004 (2)0.008 (2)0.009 (2)
C360.072 (3)0.079 (3)0.090 (3)0.029 (2)0.021 (2)0.010 (2)
Geometric parameters (Å, º) top
N1—C11.458 (4)C16—H16A0.9700
N1—C161.468 (4)C16—H16B0.9700
N1—C21.470 (4)C17—C181.377 (5)
N2—C71.445 (4)C17—C221.383 (5)
N2—C81.465 (4)C18—C191.387 (6)
N2—C361.467 (4)C18—H180.9300
N3—C91.341 (4)C19—C201.373 (7)
N3—C101.403 (4)C19—H190.9300
N3—H3A0.8600C20—C211.352 (7)
O1—C91.229 (3)C20—H200.9300
O2—C41.214 (3)C21—C221.389 (6)
C1—C51.527 (4)C21—H210.9300
C1—H1A0.9700C22—H220.9300
C1—H1B0.9700C23—C241.467 (5)
C2—C31.491 (4)C23—H230.9300
C2—H2A0.9700C24—C251.372 (5)
C2—H2B0.9700C24—C291.389 (4)
C3—C231.336 (4)C25—C261.361 (5)
C3—C41.488 (4)C25—H250.9300
C4—C51.550 (4)C26—C271.362 (5)
C5—C61.553 (4)C26—H260.9300
C5—C81.597 (4)C27—C281.371 (6)
C6—C301.513 (5)C27—H270.9300
C6—C71.521 (5)C28—C291.381 (6)
C6—H60.9800C28—H280.9300
C7—H7A0.9700C29—H290.9300
C7—H7B0.9700C30—C351.361 (5)
C8—C111.499 (4)C30—C311.372 (5)
C8—C91.564 (4)C31—C321.377 (5)
C10—C151.372 (4)C31—H310.9300
C10—C111.390 (4)C32—C331.364 (6)
C11—C121.379 (4)C32—H320.9300
C12—C131.369 (5)C33—C341.351 (6)
C12—H120.9300C33—H330.9300
C13—C141.375 (5)C34—C351.375 (5)
C13—H130.9300C34—H340.9300
C14—C151.388 (5)C35—H350.9300
C14—H140.9300C36—H36A0.9600
C15—H150.9300C36—H36B0.9600
C16—C171.510 (5)C36—H36C0.9600
C1—N1—C16112.1 (2)C14—C15—H15121.3
C1—N1—C2108.7 (2)N1—C16—C17114.3 (3)
C16—N1—C2111.1 (3)N1—C16—H16A108.7
C7—N2—C8107.0 (3)C17—C16—H16A108.7
C7—N2—C36115.6 (3)N1—C16—H16B108.7
C8—N2—C36115.4 (3)C17—C16—H16B108.7
C9—N3—C10111.7 (3)H16A—C16—H16B107.6
C9—N3—H3A124.1C18—C17—C22118.2 (4)
C10—N3—H3A124.1C18—C17—C16119.1 (4)
N1—C1—C5109.5 (2)C22—C17—C16122.7 (3)
N1—C1—H1A109.8C17—C18—C19120.6 (4)
C5—C1—H1A109.8C17—C18—H18119.7
N1—C1—H1B109.8C19—C18—H18119.7
C5—C1—H1B109.8C20—C19—C18120.4 (5)
H1A—C1—H1B108.2C20—C19—H19119.8
N1—C2—C3109.8 (3)C18—C19—H19119.8
N1—C2—H2A109.7C21—C20—C19119.5 (5)
C3—C2—H2A109.7C21—C20—H20120.3
N1—C2—H2B109.7C19—C20—H20120.3
C3—C2—H2B109.7C20—C21—C22120.8 (5)
H2A—C2—H2B108.2C20—C21—H21119.6
C23—C3—C4117.1 (3)C22—C21—H21119.6
C23—C3—C2124.3 (3)C17—C22—C21120.5 (5)
C4—C3—C2118.6 (3)C17—C22—H22119.8
O2—C4—C3122.0 (3)C21—C22—H22119.8
O2—C4—C5120.9 (3)C3—C23—C24127.8 (3)
C3—C4—C5117.1 (3)C3—C23—H23116.1
C1—C5—C4107.5 (3)C24—C23—H23116.1
C1—C5—C6113.6 (3)C25—C24—C29117.5 (3)
C4—C5—C6111.3 (2)C25—C24—C23121.8 (3)
C1—C5—C8112.4 (2)C29—C24—C23120.5 (3)
C4—C5—C8108.6 (2)C26—C25—C24122.0 (4)
C6—C5—C8103.3 (3)C26—C25—H25119.0
C30—C6—C7117.7 (3)C24—C25—H25119.0
C30—C6—C5115.6 (3)C25—C26—C27120.4 (4)
C7—C6—C5103.4 (2)C25—C26—H26119.8
C30—C6—H6106.4C27—C26—H26119.8
C7—C6—H6106.4C26—C27—C28119.4 (4)
C5—C6—H6106.4C26—C27—H27120.3
N2—C7—C6101.7 (3)C28—C27—H27120.3
N2—C7—H7A111.4C27—C28—C29120.2 (4)
C6—C7—H7A111.4C27—C28—H28119.9
N2—C7—H7B111.4C29—C28—H28119.9
C6—C7—H7B111.4C28—C29—C24120.5 (4)
H7A—C7—H7B109.3C28—C29—H29119.8
N2—C8—C11111.4 (3)C24—C29—H29119.8
N2—C8—C9111.7 (3)C35—C30—C31117.3 (3)
C11—C8—C9100.5 (2)C35—C30—C6123.0 (3)
N2—C8—C5103.3 (2)C31—C30—C6119.6 (3)
C11—C8—C5117.9 (2)C30—C31—C32121.3 (4)
C9—C8—C5112.4 (2)C30—C31—H31119.4
O1—C9—N3125.2 (3)C32—C31—H31119.4
O1—C9—C8125.9 (3)C33—C32—C31120.4 (4)
N3—C9—C8108.6 (3)C33—C32—H32119.8
C15—C10—C11122.7 (3)C31—C32—H32119.8
C15—C10—N3128.1 (3)C34—C33—C32118.6 (4)
C11—C10—N3109.1 (3)C34—C33—H33120.7
C12—C11—C10118.4 (3)C32—C33—H33120.7
C12—C11—C8131.6 (3)C33—C34—C35121.0 (4)
C10—C11—C8109.9 (3)C33—C34—H34119.5
C13—C12—C11119.5 (3)C35—C34—H34119.5
C13—C12—H12120.2C30—C35—C34121.4 (4)
C11—C12—H12120.2C30—C35—H35119.3
C12—C13—C14121.3 (3)C34—C35—H35119.3
C12—C13—H13119.3N2—C36—H36A109.5
C14—C13—H13119.3N2—C36—H36B109.5
C13—C14—C15120.4 (3)H36A—C36—H36B109.5
C13—C14—H14119.8N2—C36—H36C109.5
C15—C14—H14119.8H36A—C36—H36C109.5
C10—C15—C14117.4 (3)H36B—C36—H36C109.5
C10—C15—H15121.3
C16—N1—C1—C5162.6 (2)C15—C10—C11—C124.3 (5)
C2—N1—C1—C574.1 (3)N3—C10—C11—C12174.0 (3)
C1—N1—C2—C360.7 (3)C15—C10—C11—C8177.7 (3)
C16—N1—C2—C3175.4 (3)N3—C10—C11—C84.0 (4)
N1—C2—C3—C23139.4 (3)N2—C8—C11—C1256.1 (4)
N1—C2—C3—C438.5 (4)C9—C8—C11—C12174.6 (3)
C23—C3—C4—O229.0 (4)C5—C8—C11—C1263.0 (5)
C2—C3—C4—O2152.9 (3)N2—C8—C11—C10121.6 (3)
C23—C3—C4—C5150.3 (3)C9—C8—C11—C103.1 (3)
C2—C3—C4—C527.8 (4)C5—C8—C11—C10119.3 (3)
N1—C1—C5—C458.3 (3)C10—C11—C12—C134.2 (5)
N1—C1—C5—C6178.1 (2)C8—C11—C12—C13178.3 (3)
N1—C1—C5—C861.2 (3)C11—C12—C13—C140.7 (5)
O2—C4—C5—C1145.1 (3)C12—C13—C14—C153.0 (6)
C3—C4—C5—C135.6 (3)C11—C10—C15—C140.7 (5)
O2—C4—C5—C620.0 (4)N3—C10—C15—C14177.3 (3)
C3—C4—C5—C6160.6 (3)C13—C14—C15—C102.9 (5)
O2—C4—C5—C893.1 (3)C1—N1—C16—C17169.3 (3)
C3—C4—C5—C886.2 (3)C2—N1—C16—C1768.8 (4)
C1—C5—C6—C3028.7 (4)N1—C16—C17—C18162.4 (3)
C4—C5—C6—C3092.8 (3)N1—C16—C17—C2220.0 (5)
C8—C5—C6—C30150.7 (3)C22—C17—C18—C190.1 (5)
C1—C5—C6—C7101.5 (3)C16—C17—C18—C19177.6 (3)
C4—C5—C6—C7137.0 (3)C17—C18—C19—C200.3 (6)
C8—C5—C6—C720.6 (3)C18—C19—C20—C210.1 (7)
C8—N2—C7—C647.3 (3)C19—C20—C21—C220.8 (7)
C36—N2—C7—C6177.4 (3)C18—C17—C22—C210.6 (5)
C30—C6—C7—N2169.7 (3)C16—C17—C22—C21178.2 (3)
C5—C6—C7—N240.8 (3)C20—C21—C22—C171.1 (7)
C7—N2—C8—C11160.8 (2)C4—C3—C23—C24178.1 (3)
C36—N2—C8—C1169.0 (4)C2—C3—C23—C243.9 (5)
C7—N2—C8—C987.7 (3)C3—C23—C24—C2547.7 (5)
C36—N2—C8—C942.5 (4)C3—C23—C24—C29137.7 (3)
C7—N2—C8—C533.3 (3)C29—C24—C25—C261.2 (5)
C36—N2—C8—C5163.5 (3)C23—C24—C25—C26175.9 (3)
C1—C5—C8—N2129.2 (3)C24—C25—C26—C270.4 (6)
C4—C5—C8—N2112.0 (3)C25—C26—C27—C281.4 (6)
C6—C5—C8—N26.4 (3)C26—C27—C28—C290.8 (6)
C1—C5—C8—C11107.5 (3)C27—C28—C29—C240.9 (6)
C4—C5—C8—C1111.3 (4)C25—C24—C29—C281.8 (5)
C6—C5—C8—C11129.6 (3)C23—C24—C29—C28176.6 (3)
C1—C5—C8—C98.7 (4)C7—C6—C30—C3513.2 (5)
C4—C5—C8—C9127.5 (3)C5—C6—C30—C35109.6 (4)
C6—C5—C8—C9114.2 (3)C7—C6—C30—C31165.0 (4)
C10—N3—C9—O1175.9 (3)C5—C6—C30—C3172.1 (4)
C10—N3—C9—C81.1 (4)C35—C30—C31—C320.9 (6)
N2—C8—C9—O155.3 (4)C6—C30—C31—C32179.2 (4)
C11—C8—C9—O1173.5 (3)C30—C31—C32—C330.9 (7)
C5—C8—C9—O160.3 (4)C31—C32—C33—C340.9 (8)
N2—C8—C9—N3119.4 (3)C32—C33—C34—C350.9 (7)
C11—C8—C9—N31.2 (3)C31—C30—C35—C340.8 (6)
C5—C8—C9—N3125.0 (3)C6—C30—C35—C34179.1 (4)
C9—N3—C10—C15178.5 (3)C33—C34—C35—C300.9 (7)
C9—N3—C10—C113.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1i0.861.992.835 (3)166
C1—H1A···O10.972.342.950 (4)120
C6—H6···O20.982.292.801 (4)111
C22—H22···N10.932.572.898 (5)101
C23—H23···O20.932.472.800 (4)101
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC36H33N3O2
Mr539.65
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)8.535 (3), 11.441 (4), 15.682 (6)
α, β, γ (°)102.027 (7), 92.423 (7), 100.637 (7)
V3)1466.8 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.22 × 0.16 × 0.08
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7663, 5152, 2883
Rint0.030
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.181, 1.10
No. of reflections5152
No. of parameters372
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.25

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top
N1—C161.468 (4)N3—C101.403 (4)
N2—C361.467 (4)O1—C91.229 (3)
C1—N1—C2108.7 (2)C8—N2—C36115.4 (3)
C7—N2—C8107.0 (3)O1—C9—N3125.2 (3)
C7—N2—C8—C533.3 (3)C7—C6—C30—C3513.2 (5)
N2—C8—C9—N3119.4 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O1i0.861.992.835 (3)166
C1—H1A···O10.972.342.950 (4)120
C6—H6···O20.982.292.801 (4)111
C22—H22···N10.932.572.898 (5)101
C23—H23···O20.932.472.800 (4)101
Symmetry code: (i) x, y+1, z.
 

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