organic compounds
3-Benzylidene-1′-methyl-4′-phenyldispiro[cyclopentane-1,3′-pyrrolidine-2′,1′′-acenaphthene]-2,2′′-dione
aDepartment of Chemistry, D. G. Vaishanava College, Arumbakkam, Chennai, Tamilnadu, India, bDepartment of Chemistry, IIT Madras, Chennai, Tamilnadu, India, and cDepartment of Chemistry, Auxilium College, Vellore, India
*Correspondence e-mail: augustineap@gmail.com
In the title compound, C33H27NO2, the pyrrolidine ring adopts an with the N atom as the flap. The cyclopentanone ring adopts a twisted conformation about the Cs—CH2 bond (s = spiro link). The dihedral angle between these rings (all atoms) is 82.02 (15)°. The packing features weak C—H⋯O interactions.
Keywords: crystal structure; Claisen–Schmidt condensation; conformation.
CCDC reference: 1530096
Structure description
This work is part of a synthetic project aimed at solvent-free Claisen–Schmidt reactions of cycloalkanones with various substituted benzaldehyde (aryl aldehydes) using solid NaOH and applying a grinding technique to synthesize quantitative yields of α,α′-bis-(substituted benzylidene)cycloalkanones (Augustine et al., 2009; Prasad et al. 2011). The carbonyl group of a ketone has less additive power than that of an aldehyde: when an aldehyde condenses with it serves as a substrate for an enolized ketone. When bisbenzylidene cycloalkanones were subjected to 1,3-dipolar addition with generated through decarboxylative route by reacting a secondary amino acid with a diketone using a solvent-free microwave approach, the synthesis yielded new dispiroheterocycles, which are being further subjected to biological study. Here, we present the of the title compound.
The molecular structure consists of a pyrrolidine ring with a phenyl ring substituted in the 14 position, an acenaphthene ring in the 12 position and a benzelydine cyclopentanone ring in the 13 position (Fig. 1). The pyrrolidine (N1/C12/C13/C14/C15) ring adopts an with the N atom deviating from the plane by 0.581 (2) Å. The cyclopentanone ring (C13/C16/C17/C18/C19) is twisted about the C13—C16 bond: the dihedral angle between these rings (all atoms) is 82.02 (15)°. An intramolecular C—H⋯O interaction closes an S(9) ring. The packing features weak C—H⋯O interactions (Table 1, Fig. 2).
Synthesis and crystallization
Acenaphthenequinone (0.37 g, 2 mmol) was added to a mixture of sarcosine (0.23 g, 2 mmol), bisbenzylidene cyclopentanone (0.53 g, 2 mmol) in methanol (20 ml) and refluxed for four h at a temperature of 100°C in an oil bath. The reaction was monitored by TLC and once the reaction was complete, the reaction mixture was cooled gradually and filtered. The yellow-coloured solution was kept undisturbed for slow evaporation and the yellow solid obtained was washed with water and dried. It was recrystallized from acetone solution to give the title compound.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1530096
https://doi.org/10.1107/S2414314617005818/hb4132sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617005818/hb4132Isup2.hkl
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C33H27NO2 | Dx = 1.209 Mg m−3 |
Mr = 469.55 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 4328 reflections |
a = 17.5297 (8) Å | θ = 2.3–24.2° |
b = 12.1853 (6) Å | µ = 0.08 mm−1 |
c = 12.0781 (4) Å | T = 296 K |
V = 2579.94 (19) Å3 | Block, brown |
Z = 4 | 0.25 × 0.22 × 0.15 mm |
F(000) = 992 |
Bruker APEXII CCD diffractometer | 3171 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.019 |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | θmax = 25.0°, θmin = 2.0° |
Tmin = 0.982, Tmax = 0.989 | h = −20→15 |
10708 measured reflections | k = −14→13 |
3713 independent reflections | l = −9→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0381P)2 + 0.3666P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.11 e Å−3 |
3713 reflections | Δρmin = −0.12 e Å−3 |
327 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0048 (8) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Nitrogen H atoms were located in a difference Fourier map and refined isotropically. Other hydrogen atoms were fixed geometrically and allowed to ride on the parent carbon atoms,with aromatic C—H =0.93 Å, aliphatic C—H = 0.98 Å and methyl C—H = 0.96 Å. The displacement parameters were set for phenyl and aliphatic H atoms at Uiso(H) = 1.2Ueq(C) and for methyl H atoms at 1.5Ueq(C). |
x | y | z | Uiso*/Ueq | ||
C1 | 0.93571 (16) | 0.8127 (2) | 0.6740 (3) | 0.0534 (7) | |
C2 | 0.99936 (17) | 0.7622 (3) | 0.6124 (3) | 0.0644 (10) | |
C3 | 1.0435 (2) | 0.7980 (4) | 0.5260 (3) | 0.0979 (14) | |
H3 | 1.0345 | 0.8652 | 0.4920 | 0.117* | |
C4 | 1.1031 (3) | 0.7283 (7) | 0.4908 (5) | 0.141 (3) | |
H4 | 1.1346 | 0.7512 | 0.4334 | 0.169* | |
C5 | 1.1157 (3) | 0.6286 (7) | 0.5380 (6) | 0.144 (3) | |
H5 | 1.1542 | 0.5843 | 0.5093 | 0.173* | |
C6 | 1.0732 (2) | 0.5901 (5) | 0.6282 (4) | 0.0980 (16) | |
C7 | 1.0820 (3) | 0.4918 (5) | 0.6910 (6) | 0.127 (2) | |
H7 | 1.1192 | 0.4411 | 0.6713 | 0.153* | |
C8 | 1.0367 (3) | 0.4721 (4) | 0.7787 (6) | 0.123 (2) | |
H8 | 1.0448 | 0.4085 | 0.8196 | 0.147* | |
C9 | 0.9774 (2) | 0.5434 (3) | 0.8115 (4) | 0.0817 (11) | |
H9 | 0.9474 | 0.5274 | 0.8730 | 0.098* | |
C10 | 0.96486 (15) | 0.6368 (2) | 0.7509 (3) | 0.0565 (8) | |
C11 | 1.01347 (16) | 0.6597 (3) | 0.6619 (3) | 0.0663 (10) | |
C12 | 0.90674 (14) | 0.7280 (2) | 0.7623 (2) | 0.0438 (6) | |
C13 | 0.82020 (13) | 0.6964 (2) | 0.7387 (2) | 0.0364 (6) | |
C14 | 0.77458 (14) | 0.7685 (2) | 0.8232 (2) | 0.0418 (6) | |
H14 | 0.7537 | 0.7180 | 0.8786 | 0.050* | |
C15 | 0.83459 (16) | 0.8372 (2) | 0.8822 (3) | 0.0551 (8) | |
H15A | 0.8415 | 0.9074 | 0.8457 | 0.066* | |
H15B | 0.8206 | 0.8498 | 0.9589 | 0.066* | |
C16 | 0.79650 (16) | 0.7002 (2) | 0.6165 (2) | 0.0411 (6) | |
H16A | 0.7416 | 0.7082 | 0.6099 | 0.049* | |
H16B | 0.8208 | 0.7615 | 0.5793 | 0.049* | |
C17 | 0.82258 (16) | 0.5913 (2) | 0.5654 (2) | 0.0433 (6) | |
H17A | 0.7896 | 0.5702 | 0.5045 | 0.052* | |
H17B | 0.8746 | 0.5966 | 0.5386 | 0.052* | |
C18 | 0.81684 (13) | 0.5107 (2) | 0.6590 (2) | 0.0396 (6) | |
C19 | 0.81010 (14) | 0.5735 (2) | 0.7635 (2) | 0.0402 (6) | |
C20 | 0.81731 (15) | 0.4010 (2) | 0.6616 (3) | 0.0479 (7) | |
H20 | 0.8139 | 0.3711 | 0.7322 | 0.057* | |
C21 | 0.82230 (16) | 0.3197 (2) | 0.5728 (3) | 0.0508 (7) | |
C22 | 0.82514 (16) | 0.3441 (2) | 0.4606 (3) | 0.0554 (8) | |
H22 | 0.8268 | 0.4171 | 0.4383 | 0.066* | |
C23 | 0.82559 (18) | 0.2628 (3) | 0.3820 (3) | 0.0674 (9) | |
H23 | 0.8258 | 0.2812 | 0.3072 | 0.081* | |
C24 | 0.8257 (2) | 0.1547 (3) | 0.4131 (4) | 0.0839 (12) | |
H24 | 0.8261 | 0.0996 | 0.3598 | 0.101* | |
C25 | 0.8253 (3) | 0.1285 (3) | 0.5224 (4) | 0.0994 (15) | |
H25 | 0.8266 | 0.0552 | 0.5437 | 0.119* | |
C26 | 0.8230 (2) | 0.2089 (3) | 0.6015 (3) | 0.0809 (12) | |
H26 | 0.8218 | 0.1892 | 0.6758 | 0.097* | |
C27 | 0.70803 (15) | 0.8330 (2) | 0.7781 (2) | 0.0419 (6) | |
C28 | 0.63472 (17) | 0.8051 (3) | 0.8076 (3) | 0.0578 (8) | |
H28 | 0.6266 | 0.7474 | 0.8567 | 0.069* | |
C29 | 0.57249 (19) | 0.8620 (3) | 0.7648 (3) | 0.0754 (10) | |
H29 | 0.5232 | 0.8410 | 0.7841 | 0.091* | |
C30 | 0.5834 (2) | 0.9485 (3) | 0.6946 (3) | 0.0693 (10) | |
H30 | 0.5418 | 0.9867 | 0.6663 | 0.083* | |
C31 | 0.6562 (2) | 0.9785 (2) | 0.6660 (3) | 0.0652 (9) | |
H31 | 0.6641 | 1.0378 | 0.6188 | 0.078* | |
C32 | 0.71770 (17) | 0.9211 (2) | 0.7069 (3) | 0.0532 (8) | |
H32 | 0.7667 | 0.9419 | 0.6864 | 0.064* | |
C33 | 0.97241 (19) | 0.8233 (3) | 0.9159 (3) | 0.0843 (12) | |
H33A | 0.9665 | 0.8398 | 0.9932 | 0.126* | |
H33B | 0.9814 | 0.8900 | 0.8756 | 0.126* | |
H33C | 1.0149 | 0.7746 | 0.9062 | 0.126* | |
N1 | 0.90293 (13) | 0.7708 (2) | 0.8745 (2) | 0.0535 (6) | |
O1 | 0.91109 (12) | 0.90536 (17) | 0.6635 (2) | 0.0719 (7) | |
O2 | 0.79755 (12) | 0.53556 (15) | 0.85476 (16) | 0.0554 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0431 (16) | 0.0577 (18) | 0.0594 (19) | −0.0134 (14) | 0.0008 (15) | −0.0130 (16) |
C2 | 0.0444 (18) | 0.091 (3) | 0.058 (2) | −0.0234 (17) | 0.0139 (16) | −0.0315 (18) |
C3 | 0.074 (3) | 0.147 (4) | 0.072 (3) | −0.048 (3) | 0.027 (2) | −0.039 (3) |
C4 | 0.085 (4) | 0.232 (7) | 0.106 (5) | −0.066 (5) | 0.055 (3) | −0.092 (5) |
C5 | 0.058 (3) | 0.224 (7) | 0.151 (6) | −0.016 (4) | 0.025 (3) | −0.129 (6) |
C6 | 0.0384 (19) | 0.135 (4) | 0.120 (4) | 0.006 (2) | −0.001 (2) | −0.081 (3) |
C7 | 0.062 (3) | 0.119 (4) | 0.201 (7) | 0.045 (3) | −0.025 (4) | −0.076 (4) |
C8 | 0.077 (3) | 0.097 (3) | 0.194 (6) | 0.048 (3) | −0.049 (4) | −0.033 (4) |
C9 | 0.056 (2) | 0.076 (2) | 0.112 (3) | 0.0186 (17) | −0.028 (2) | −0.005 (2) |
C10 | 0.0371 (16) | 0.0611 (19) | 0.071 (2) | 0.0054 (13) | −0.0108 (16) | −0.0189 (17) |
C11 | 0.0342 (16) | 0.086 (2) | 0.079 (2) | −0.0023 (15) | −0.0017 (17) | −0.046 (2) |
C12 | 0.0372 (16) | 0.0470 (15) | 0.0470 (16) | 0.0022 (11) | 0.0013 (12) | −0.0076 (13) |
C13 | 0.0350 (14) | 0.0370 (13) | 0.0371 (14) | 0.0017 (11) | 0.0027 (11) | −0.0002 (11) |
C14 | 0.0395 (15) | 0.0442 (15) | 0.0416 (15) | 0.0015 (12) | 0.0075 (13) | 0.0003 (12) |
C15 | 0.0541 (18) | 0.0648 (19) | 0.0465 (17) | 0.0049 (15) | 0.0007 (14) | −0.0191 (15) |
C16 | 0.0447 (15) | 0.0361 (14) | 0.0425 (15) | 0.0009 (12) | −0.0001 (12) | 0.0020 (11) |
C17 | 0.0496 (16) | 0.0405 (14) | 0.0398 (15) | −0.0002 (12) | −0.0049 (12) | 0.0014 (12) |
C18 | 0.0358 (13) | 0.0397 (14) | 0.0434 (15) | 0.0012 (11) | −0.0023 (12) | 0.0016 (13) |
C19 | 0.0335 (14) | 0.0443 (15) | 0.0429 (17) | 0.0050 (11) | −0.0012 (12) | 0.0037 (14) |
C20 | 0.0503 (16) | 0.0417 (15) | 0.0516 (17) | 0.0034 (12) | 0.0024 (14) | 0.0045 (15) |
C21 | 0.0454 (17) | 0.0412 (15) | 0.066 (2) | 0.0016 (13) | 0.0075 (14) | −0.0016 (15) |
C22 | 0.0570 (19) | 0.0480 (17) | 0.061 (2) | 0.0102 (14) | 0.0029 (16) | −0.0055 (16) |
C23 | 0.064 (2) | 0.069 (2) | 0.069 (2) | 0.0068 (17) | 0.0054 (17) | −0.0149 (19) |
C24 | 0.085 (3) | 0.062 (2) | 0.104 (3) | −0.0154 (18) | 0.032 (2) | −0.036 (2) |
C25 | 0.152 (4) | 0.0392 (19) | 0.107 (4) | −0.009 (2) | 0.050 (3) | −0.012 (2) |
C26 | 0.121 (3) | 0.0409 (19) | 0.081 (3) | −0.0010 (19) | 0.028 (2) | 0.0016 (18) |
C27 | 0.0426 (16) | 0.0373 (14) | 0.0457 (16) | 0.0053 (11) | 0.0030 (12) | −0.0080 (12) |
C28 | 0.0470 (18) | 0.0608 (19) | 0.066 (2) | 0.0016 (14) | 0.0020 (15) | 0.0001 (16) |
C29 | 0.0418 (19) | 0.098 (3) | 0.087 (3) | 0.0081 (17) | −0.0003 (18) | −0.008 (2) |
C30 | 0.067 (2) | 0.074 (2) | 0.067 (2) | 0.0315 (18) | −0.0118 (17) | −0.0145 (19) |
C31 | 0.080 (2) | 0.0495 (18) | 0.066 (2) | 0.0205 (16) | −0.0039 (19) | −0.0029 (17) |
C32 | 0.0540 (18) | 0.0440 (16) | 0.0617 (19) | 0.0068 (14) | 0.0035 (14) | −0.0021 (14) |
C33 | 0.053 (2) | 0.120 (3) | 0.080 (3) | 0.001 (2) | −0.0162 (19) | −0.041 (2) |
N1 | 0.0401 (13) | 0.0727 (16) | 0.0476 (14) | 0.0061 (12) | −0.0071 (11) | −0.0186 (12) |
O1 | 0.0697 (15) | 0.0557 (13) | 0.0903 (17) | −0.0123 (11) | 0.0091 (13) | 0.0087 (13) |
O2 | 0.0716 (13) | 0.0508 (12) | 0.0438 (12) | 0.0039 (10) | 0.0067 (10) | 0.0085 (9) |
C1—O1 | 1.216 (3) | C17—C18 | 1.501 (4) |
C1—C2 | 1.476 (4) | C17—H17A | 0.9700 |
C1—C12 | 1.568 (4) | C17—H17B | 0.9700 |
C2—C3 | 1.370 (5) | C18—C20 | 1.338 (3) |
C2—C11 | 1.406 (5) | C18—C19 | 1.480 (4) |
C3—C4 | 1.412 (8) | C19—O2 | 1.216 (3) |
C3—H3 | 0.9300 | C20—C21 | 1.462 (4) |
C4—C5 | 1.360 (9) | C20—H20 | 0.9300 |
C4—H4 | 0.9300 | C21—C22 | 1.388 (4) |
C5—C6 | 1.401 (9) | C21—C26 | 1.394 (4) |
C5—H5 | 0.9300 | C22—C23 | 1.372 (4) |
C6—C11 | 1.408 (5) | C22—H22 | 0.9300 |
C6—C7 | 1.426 (8) | C23—C24 | 1.371 (5) |
C7—C8 | 1.345 (8) | C23—H23 | 0.9300 |
C7—H7 | 0.9300 | C24—C25 | 1.357 (6) |
C8—C9 | 1.412 (6) | C24—H24 | 0.9300 |
C8—H8 | 0.9300 | C25—C26 | 1.369 (5) |
C9—C10 | 1.370 (5) | C25—H25 | 0.9300 |
C9—H9 | 0.9300 | C26—H26 | 0.9300 |
C10—C11 | 1.400 (5) | C27—C28 | 1.376 (4) |
C10—C12 | 1.514 (4) | C27—C32 | 1.386 (4) |
C12—N1 | 1.454 (3) | C28—C29 | 1.392 (4) |
C12—C13 | 1.591 (3) | C28—H28 | 0.9300 |
C13—C16 | 1.534 (4) | C29—C30 | 1.366 (5) |
C13—C19 | 1.538 (4) | C29—H29 | 0.9300 |
C13—C14 | 1.567 (4) | C30—C31 | 1.372 (5) |
C14—C27 | 1.508 (4) | C30—H30 | 0.9300 |
C14—C15 | 1.522 (4) | C31—C32 | 1.376 (4) |
C14—H14 | 0.9800 | C31—H31 | 0.9300 |
C15—N1 | 1.449 (4) | C32—H32 | 0.9300 |
C15—H15A | 0.9700 | C33—N1 | 1.464 (4) |
C15—H15B | 0.9700 | C33—H33A | 0.9600 |
C16—C17 | 1.533 (4) | C33—H33B | 0.9600 |
C16—H16A | 0.9700 | C33—H33C | 0.9600 |
C16—H16B | 0.9700 | ||
O1—C1—C2 | 127.1 (3) | H16A—C16—H16B | 108.7 |
O1—C1—C12 | 124.6 (3) | C18—C17—C16 | 104.1 (2) |
C2—C1—C12 | 108.2 (3) | C18—C17—H17A | 110.9 |
C3—C2—C11 | 120.5 (4) | C16—C17—H17A | 110.9 |
C3—C2—C1 | 132.7 (4) | C18—C17—H17B | 110.9 |
C11—C2—C1 | 106.8 (3) | C16—C17—H17B | 110.9 |
C2—C3—C4 | 117.1 (5) | H17A—C17—H17B | 109.0 |
C2—C3—H3 | 121.4 | C20—C18—C19 | 119.8 (3) |
C4—C3—H3 | 121.4 | C20—C18—C17 | 132.1 (3) |
C5—C4—C3 | 122.1 (6) | C19—C18—C17 | 108.0 (2) |
C5—C4—H4 | 119.0 | O2—C19—C18 | 126.2 (2) |
C3—C4—H4 | 119.0 | O2—C19—C13 | 124.6 (2) |
C4—C5—C6 | 122.6 (5) | C18—C19—C13 | 109.2 (2) |
C4—C5—H5 | 118.7 | C18—C20—C21 | 131.3 (3) |
C6—C5—H5 | 118.7 | C18—C20—H20 | 114.3 |
C5—C6—C11 | 114.8 (6) | C21—C20—H20 | 114.3 |
C5—C6—C7 | 129.6 (5) | C22—C21—C26 | 116.7 (3) |
C11—C6—C7 | 115.6 (5) | C22—C21—C20 | 125.0 (3) |
C8—C7—C6 | 120.3 (4) | C26—C21—C20 | 118.3 (3) |
C8—C7—H7 | 119.8 | C23—C22—C21 | 121.5 (3) |
C6—C7—H7 | 119.8 | C23—C22—H22 | 119.3 |
C7—C8—C9 | 123.1 (5) | C21—C22—H22 | 119.3 |
C7—C8—H8 | 118.5 | C24—C23—C22 | 120.2 (4) |
C9—C8—H8 | 118.5 | C24—C23—H23 | 119.9 |
C10—C9—C8 | 118.6 (5) | C22—C23—H23 | 119.9 |
C10—C9—H9 | 120.7 | C25—C24—C23 | 119.5 (3) |
C8—C9—H9 | 120.7 | C25—C24—H24 | 120.2 |
C9—C10—C11 | 118.6 (3) | C23—C24—H24 | 120.2 |
C9—C10—C12 | 132.0 (3) | C24—C25—C26 | 120.7 (4) |
C11—C10—C12 | 109.4 (3) | C24—C25—H25 | 119.7 |
C10—C11—C2 | 113.3 (3) | C26—C25—H25 | 119.7 |
C10—C11—C6 | 123.7 (4) | C25—C26—C21 | 121.4 (4) |
C2—C11—C6 | 122.9 (4) | C25—C26—H26 | 119.3 |
N1—C12—C10 | 112.2 (2) | C21—C26—H26 | 119.3 |
N1—C12—C1 | 114.4 (2) | C28—C27—C32 | 117.8 (3) |
C10—C12—C1 | 101.7 (2) | C28—C27—C14 | 120.0 (2) |
N1—C12—C13 | 102.1 (2) | C32—C27—C14 | 122.2 (2) |
C10—C12—C13 | 116.6 (2) | C27—C28—C29 | 120.8 (3) |
C1—C12—C13 | 110.3 (2) | C27—C28—H28 | 119.6 |
C16—C13—C19 | 100.7 (2) | C29—C28—H28 | 119.6 |
C16—C13—C14 | 118.2 (2) | C30—C29—C28 | 120.3 (3) |
C19—C13—C14 | 111.1 (2) | C30—C29—H29 | 119.8 |
C16—C13—C12 | 115.1 (2) | C28—C29—H29 | 119.8 |
C19—C13—C12 | 108.09 (19) | C29—C30—C31 | 119.5 (3) |
C14—C13—C12 | 103.56 (19) | C29—C30—H30 | 120.2 |
C27—C14—C15 | 114.7 (2) | C31—C30—H30 | 120.2 |
C27—C14—C13 | 116.8 (2) | C30—C31—C32 | 120.1 (3) |
C15—C14—C13 | 105.1 (2) | C30—C31—H31 | 119.9 |
C27—C14—H14 | 106.5 | C32—C31—H31 | 119.9 |
C15—C14—H14 | 106.5 | C31—C32—C27 | 121.4 (3) |
C13—C14—H14 | 106.5 | C31—C32—H32 | 119.3 |
N1—C15—C14 | 103.5 (2) | C27—C32—H32 | 119.3 |
N1—C15—H15A | 111.1 | N1—C33—H33A | 109.5 |
C14—C15—H15A | 111.1 | N1—C33—H33B | 109.5 |
N1—C15—H15B | 111.1 | H33A—C33—H33B | 109.5 |
C14—C15—H15B | 111.1 | N1—C33—H33C | 109.5 |
H15A—C15—H15B | 109.0 | H33A—C33—H33C | 109.5 |
C17—C16—C13 | 106.3 (2) | H33B—C33—H33C | 109.5 |
C17—C16—H16A | 110.5 | C15—N1—C12 | 107.4 (2) |
C13—C16—H16A | 110.5 | C15—N1—C33 | 114.9 (2) |
C17—C16—H16B | 110.5 | C12—N1—C33 | 115.9 (2) |
C13—C16—H16B | 110.5 | ||
O1—C1—C2—C3 | −5.0 (6) | C19—C13—C14—C15 | 118.6 (2) |
C12—C1—C2—C3 | 178.1 (3) | C12—C13—C14—C15 | 2.7 (3) |
O1—C1—C2—C11 | 172.8 (3) | C27—C14—C15—N1 | −156.4 (2) |
C12—C1—C2—C11 | −4.1 (3) | C13—C14—C15—N1 | −26.7 (3) |
C11—C2—C3—C4 | −0.6 (5) | C19—C13—C16—C17 | −34.0 (3) |
C1—C2—C3—C4 | 176.9 (4) | C14—C13—C16—C17 | −155.1 (2) |
C2—C3—C4—C5 | 1.5 (8) | C12—C13—C16—C17 | 82.0 (3) |
C3—C4—C5—C6 | −3.1 (10) | C13—C16—C17—C18 | 31.4 (3) |
C4—C5—C6—C11 | 3.6 (8) | C16—C17—C18—C20 | 165.0 (3) |
C4—C5—C6—C7 | −175.9 (6) | C16—C17—C18—C19 | −15.4 (3) |
C5—C6—C7—C8 | 177.1 (5) | C20—C18—C19—O2 | −7.3 (4) |
C11—C6—C7—C8 | −2.4 (7) | C17—C18—C19—O2 | 173.0 (3) |
C6—C7—C8—C9 | 2.1 (8) | C20—C18—C19—C13 | 173.6 (2) |
C7—C8—C9—C10 | 0.5 (7) | C17—C18—C19—C13 | −6.1 (3) |
C8—C9—C10—C11 | −2.6 (5) | C16—C13—C19—O2 | −154.5 (2) |
C8—C9—C10—C12 | 179.1 (3) | C14—C13—C19—O2 | −28.4 (3) |
C9—C10—C11—C2 | −174.6 (3) | C12—C13—C19—O2 | 84.5 (3) |
C12—C10—C11—C2 | 4.1 (3) | C16—C13—C19—C18 | 24.6 (2) |
C9—C10—C11—C6 | 2.3 (5) | C14—C13—C19—C18 | 150.6 (2) |
C12—C10—C11—C6 | −179.1 (3) | C12—C13—C19—C18 | −96.4 (2) |
C3—C2—C11—C10 | 178.3 (3) | C19—C18—C20—C21 | 179.2 (3) |
C1—C2—C11—C10 | 0.2 (3) | C17—C18—C20—C21 | −1.3 (5) |
C3—C2—C11—C6 | 1.3 (5) | C18—C20—C21—C22 | −2.4 (5) |
C1—C2—C11—C6 | −176.7 (3) | C18—C20—C21—C26 | 178.8 (3) |
C5—C6—C11—C10 | −179.3 (4) | C26—C21—C22—C23 | 2.4 (4) |
C7—C6—C11—C10 | 0.2 (5) | C20—C21—C22—C23 | −176.4 (3) |
C5—C6—C11—C2 | −2.7 (5) | C21—C22—C23—C24 | −2.1 (5) |
C7—C6—C11—C2 | 176.8 (3) | C22—C23—C24—C25 | 0.1 (6) |
C9—C10—C12—N1 | 49.6 (4) | C23—C24—C25—C26 | 1.5 (7) |
C11—C10—C12—N1 | −128.8 (3) | C24—C25—C26—C21 | −1.1 (7) |
C9—C10—C12—C1 | 172.3 (3) | C22—C21—C26—C25 | −0.8 (5) |
C11—C10—C12—C1 | −6.1 (3) | C20—C21—C26—C25 | 178.1 (4) |
C9—C10—C12—C13 | −67.7 (4) | C15—C14—C27—C28 | −125.1 (3) |
C11—C10—C12—C13 | 113.9 (3) | C13—C14—C27—C28 | 111.3 (3) |
O1—C1—C12—N1 | −49.6 (4) | C15—C14—C27—C32 | 54.9 (4) |
C2—C1—C12—N1 | 127.4 (2) | C13—C14—C27—C32 | −68.8 (3) |
O1—C1—C12—C10 | −170.9 (3) | C32—C27—C28—C29 | 1.6 (4) |
C2—C1—C12—C10 | 6.1 (3) | C14—C27—C28—C29 | −178.5 (3) |
O1—C1—C12—C13 | 64.8 (4) | C27—C28—C29—C30 | −1.5 (5) |
C2—C1—C12—C13 | −118.2 (2) | C28—C29—C30—C31 | 0.4 (5) |
N1—C12—C13—C16 | 152.4 (2) | C29—C30—C31—C32 | 0.7 (5) |
C10—C12—C13—C16 | −84.9 (3) | C30—C31—C32—C27 | −0.6 (5) |
C1—C12—C13—C16 | 30.5 (3) | C28—C27—C32—C31 | −0.6 (4) |
N1—C12—C13—C19 | −96.0 (2) | C14—C27—C32—C31 | 179.5 (3) |
C10—C12—C13—C19 | 26.7 (3) | C14—C15—N1—C12 | 43.6 (3) |
C1—C12—C13—C19 | 142.0 (2) | C14—C15—N1—C33 | 174.2 (3) |
N1—C12—C13—C14 | 21.9 (2) | C10—C12—N1—C15 | −166.6 (2) |
C10—C12—C13—C14 | 144.7 (2) | C1—C12—N1—C15 | 78.1 (3) |
C1—C12—C13—C14 | −100.0 (2) | C13—C12—N1—C15 | −41.0 (3) |
C16—C13—C14—C27 | 2.6 (3) | C10—C12—N1—C33 | 63.3 (3) |
C19—C13—C14—C27 | −113.1 (2) | C1—C12—N1—C33 | −51.9 (3) |
C12—C13—C14—C27 | 131.1 (2) | C13—C12—N1—C33 | −171.0 (3) |
C16—C13—C14—C15 | −125.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C32—H32···O1 | 0.93 | 2.58 | 3.436 (4) | 152 |
C5—H5···O2i | 0.93 | 2.52 | 3.348 (8) | 149 |
C17—H17A···O2ii | 0.97 | 2.40 | 3.372 (3) | 174 |
Symmetry codes: (i) −x+2, −y+1, z−1/2; (ii) −x+3/2, y, z−1/2. |
Acknowledgements
The authors acknowledge Department of Chemistry, IIT Madras, for the X-ray data collection.
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