In the title compound, the pyrrolidine ring adopts an envelope conformation, which may be correlated with the intramolecular O—H⋯N hydrogen bond.
Keywords: crystal structure, Mannich bases, semi-empirical, methylphenyl, intramolecular O—H⋯N hydrogen bond
Abstract
In the title compound, C20H21NO2, the pyrrolidine ring adopts an envelope conformation with the N atom at the flap position. The central benzene ring makes dihedral angles of 21.39 (10) and 80.10 (15)° with the phenyl ring and the mean plane of the pyrrolidine ring, respectively. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, which closes an S(6) ring. A weak C—H⋯π interaction is observed in the crystal.
Chemical context
Mannich bases are a group of compounds having various biological activities such as cytotoxic (Bilginer et al., 2013 ▸), anti-inflammatory (Sahin et al., 2010 ▸) and anticonvulsant (Gul et al., 2004 ▸) activities. α,β-Unsaturated ketones present in the chemical structure of Mannich bases themselves or those produced from them by deamination processes are responsible for their cytotoxicity.
The cytotoxic and anticancer properties of chalcone (1,3-diphenyl-2-propenone) and related compounds have been reported (Bilginer et al., 2013 ▸; Dimmock et al., 1998 ▸; Gul Cizmecioglu et al., 2009 ▸); Gul Mete et al., 2009 ▸). The title compound, (I), reported in this study is a Mannich base of phenolic chalcone.
Structural commentary
In the title compound (Fig. 1 ▸), the pyrrolidine ring (N1/C17–C20) exhibits an envelope conformation with the N atom at the flap position [the puckering parameters are Q(2) = 0.350 (3) Å and φ(2) = 186.9 (5)°]. The central benzene ring (C10–C15) makes dihedral angles of 21.39 (10) and 80.10 (15)°, with the phenyl ring (C1–C6) and the mean plane of the pyrrolidine ring (N1/C17–C20), respectively. Otherwise, the geometrical parameters for (I) are comparable those reported for related compounds (Suhud et al., 2015 ▸; Palakshamurthy et al., 2012 ▸). An intramolecular O2—H1O⋯N1 hydrogen bond (Table 1 ▸, Fig. 2 ▸) helps to establish the molecular conformation of (I).
Figure 1.
View of the molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
Table 1. Hydrogen-bond geometry (Å, °).
Cg3 is the centroid of the C10–C15 ring.
| D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A |
|---|---|---|---|---|
| O2—H1O⋯N1 | 0.85 (3) | 1.85 (3) | 2.633 (2) | 154 (3) |
| C5—H5⋯Cg3i | 0.93 | 2.99 | 3.685 (2) | 132 |
Symmetry code: (i) 
.
Figure 2.
The molecular packing and hydrogen bonding viewed down the a axis.
Supramolecular features
The only directional interaction present in the crystal of (I) is a very weak C—H⋯π bond (Table 1 ▸).
Semi-empirical quantum-mechanical calculations
A theoretical calculation was carried out using the semi-empirical quantum-mechanical CNDO/2 (Complete Neglect of Differential Overlap) method (Pople & Beveridge, 1970 ▸). The spatial view of the single molecule, with atomic labels, calculated as a closed-shell in a vacuum is shown in Fig. 3 ▸. The charges at atoms O1, O2 and N1 are −0.337, −0.271 and −0.159 e−, respectively. The calculated dipole moment is 2.760 Debye.
Figure 3.
The conformation of the title compound, calculated using the CNDO method.
Biological activity
Compound (I) was tested against human hepatoma (Huh7) and breast cancer cell (T47D) lines in terms of its cytotoxic activities, and showed activities against both cell lines used, especially against the T47D cell line. The compound studied here may serve as a model compound for designing new anticancer compounds for further studies (Yerdelen, 2009 ▸).
Synthesis and crystallization
A solution of paraformaldehyde (0.132 g; 4.4 mmol) and pyrrolidine (0.317 g, 4.4 mmol) in acetonitrile (5 mL) was heated under reflux at 353 K for 30 min. A solution of the chalcone, 1-(4-hydroxyphenyl)-3-phenyl-2-propen-1-one (1 g, 4.4 mmol) in acetonitrile (25 ml), was added to the reaction flask and heating was continued. The reaction was monitored by thin layer chromatography (TLC) and stopped after 7.5 h. The reaction solvent was distilled under vacuum. The residue was purified by column chromatography using Al2O3 as adsorbant and CHCl3/MeOH (9:1) as eluent. The title compound was obtained in 44% yield (m.p. = 398–402 K).Crystals suitable for X-ray diffaction analysis were obtained by recrystallization from ehanol.
1H NMR (CDCl3, p.p.m.) δ 1.89–1.86 (m, 4H, C18-H, C19-H); 2.67 (br s, 4H, C17-H, C20-H); 3.90 (s, 2H, C16-H); 6.88–6.86 (d, 1H, C14-H); 7.41–7.39 (m, 3H, C3-H, C4-H, C5-H); 7.56–7.53 (d, 1H, C8-H, J = 15.4 Hz); 7.65–7.62 (m, 2H, C2-H, C6-H); 7.78–7.77 (d, 1H, C11-H); 7.80–7.76 (d, 1H, C7-H, J = 15.4 Hz); 7.92–7.90 (dd, 1H, C15-H);
13C NMR (CDCl3, p.p.m.) δ 188.82 (C9), 163.59 (C13), 143.77 (C7), 135.42 (C1), 130.43 (C11), 130.39 (C15), 129.60 (C10), 129.25 (C3, C5), 129.12 (C4), 128.55 (C2, C6), 122.68 (C12), 122.16 (C8), 116.15 (C14), 50.80 (C16), 53.69 (C17, C20), 23.88 (C18, C19); TOF MS [ES (−)] (CHCl3) m/z: M + (307.15), M +-1 (306.15) (Yerdelen, 2009 ▸).
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Carbon-bound H atoms were placed in calculated positions with C—H = 0.93 and 0.97 Å, and refined using a riding model with U iso(H) = 1.2U eq(C). The hydroxyl H atom was found from a difference Fourier map and its positional parameters were freely refined with U iso(H) = 1.5U eq(O). The most disagreeable reflections (2 4 0), (4 9 0), (4 12 0), (5 12 4), (3 12 5), (3 3 1), (0 16 5), (1 3 0), (2 20 6), (−2 13 17), (0 5 4), (0 11 4) and (2 13 4) were omitted in the final cycles of refinement. The Flack absolute structure parameter was found to be indeterminate in the present study.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C20H21NO2 |
| M r | 307.38 |
| Crystal system, space group | Orthorhombic, P212121 |
| Temperature (K) | 296 |
| a, b, c (Å) | 5.8403 (5), 16.3195 (13), 17.3615 (14) |
| V (Å3) | 1654.7 (2) |
| Z | 4 |
| Radiation type | Mo Kα |
| μ (mm−1) | 0.08 |
| Crystal size (mm) | 0.66 × 0.53 × 0.33 |
| Data collection | |
| Diffractometer | Bruker APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2007 ▸) |
| T min, T max | 0.951, 0.974 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 37526, 4120, 3647 |
| R int | 0.050 |
| (sin θ/λ)max (Å−1) | 0.668 |
| Refinement | |
| R[F 2 > 2σ(F 2)], wR(F 2), S | 0.043, 0.118, 1.03 |
| No. of reflections | 4120 |
| No. of parameters | 211 |
| No. of restraints | 1 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.24, −0.12 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989016006009/hb7576sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016006009/hb7576Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016006009/hb7576Isup3.cml
CCDC reference: 1473395
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors acknowledge the Aksaray University, Science and Technology Application and Research Center, Aksaray,Turkey, for the use of the Bruker SMART BREEZE CCD diffractometer (purchased under grant No. 2010 K120480 of the State of Planning Organization)
supplementary crystallographic information
Crystal data
| C20H21NO2 | F(000) = 656 |
| Mr = 307.38 | Dx = 1.234 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 4120 reflections |
| a = 5.8403 (5) Å | θ = 2.4–27.7° |
| b = 16.3195 (13) Å | µ = 0.08 mm−1 |
| c = 17.3615 (14) Å | T = 296 K |
| V = 1654.7 (2) Å3 | Prism, light yellow |
| Z = 4 | 0.66 × 0.53 × 0.33 mm |
Data collection
| Bruker APEXII CCD diffractometer | 4120 independent reflections |
| Radiation source: sealed tube | 3647 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.050 |
| φ and ω scans | θmax = 28.4°, θmin = 1.7° |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −7→7 |
| Tmin = 0.951, Tmax = 0.974 | k = −21→21 |
| 37526 measured reflections | l = −23→23 |
Refinement
| Refinement on F2 | 1 restraint |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.068P)2 + 0.1361P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max < 0.001 |
| 4120 reflections | Δρmax = 0.24 e Å−3 |
| 211 parameters | Δρmin = −0.12 e Å−3 |
Special details
| 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 esds are taken into account in the estimation of distances, angles and torsion angles |
| Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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)
| x | y | z | Uiso*/Ueq | ||
| O1 | −0.0436 (3) | 0.72582 (11) | 0.13185 (14) | 0.0800 (7) | |
| O2 | 0.4920 (3) | 0.42033 (9) | 0.00124 (10) | 0.0578 (5) | |
| N1 | 0.1759 (3) | 0.34948 (10) | 0.08639 (10) | 0.0495 (5) | |
| C1 | 0.3003 (4) | 0.98751 (12) | 0.23067 (13) | 0.0524 (6) | |
| C2 | 0.4274 (5) | 1.05592 (14) | 0.25148 (13) | 0.0607 (7) | |
| C3 | 0.6363 (4) | 1.06897 (14) | 0.21774 (14) | 0.0610 (7) | |
| C4 | 0.7188 (4) | 1.01504 (15) | 0.16329 (13) | 0.0602 (7) | |
| C5 | 0.5935 (4) | 0.94596 (13) | 0.14348 (12) | 0.0534 (6) | |
| C6 | 0.3823 (3) | 0.93109 (11) | 0.17767 (10) | 0.0443 (5) | |
| C7 | 0.2469 (4) | 0.85825 (12) | 0.15995 (12) | 0.0498 (6) | |
| C8 | 0.3149 (4) | 0.79067 (12) | 0.12533 (12) | 0.0511 (6) | |
| C9 | 0.1583 (4) | 0.72064 (12) | 0.11351 (13) | 0.0499 (6) | |
| C10 | 0.2497 (3) | 0.64318 (11) | 0.08086 (10) | 0.0431 (5) | |
| C11 | 0.4636 (4) | 0.63705 (12) | 0.04543 (11) | 0.0466 (6) | |
| C12 | 0.5411 (4) | 0.56234 (13) | 0.01826 (11) | 0.0495 (6) | |
| C13 | 0.4084 (3) | 0.49271 (12) | 0.02654 (11) | 0.0441 (5) | |
| C14 | 0.1907 (3) | 0.49728 (11) | 0.06048 (11) | 0.0433 (5) | |
| C15 | 0.1167 (3) | 0.57238 (12) | 0.08719 (11) | 0.0441 (5) | |
| C16 | 0.0423 (4) | 0.42179 (13) | 0.06449 (14) | 0.0550 (6) | |
| C17 | 0.2614 (5) | 0.35266 (14) | 0.16535 (14) | 0.0648 (8) | |
| C18 | 0.3247 (6) | 0.26561 (15) | 0.18383 (17) | 0.0787 (10) | |
| C19 | 0.1771 (7) | 0.21350 (17) | 0.1318 (2) | 0.0941 (13) | |
| C20 | 0.0483 (5) | 0.27222 (14) | 0.08114 (18) | 0.0719 (9) | |
| H1 | 0.15700 | 0.97930 | 0.25270 | 0.0630* | |
| H1O | 0.418 (6) | 0.3850 (16) | 0.0268 (18) | 0.0870* | |
| H2 | 0.37130 | 1.09250 | 0.28800 | 0.0730* | |
| H3 | 0.72280 | 1.11450 | 0.23160 | 0.0730* | |
| H4 | 0.85910 | 1.02500 | 0.13970 | 0.0720* | |
| H5 | 0.65110 | 0.90950 | 0.10720 | 0.0640* | |
| H7 | 0.09410 | 0.85980 | 0.17490 | 0.0600* | |
| H8 | 0.46510 | 0.78690 | 0.10790 | 0.0610* | |
| H11 | 0.55450 | 0.68350 | 0.04010 | 0.0560* | |
| H12 | 0.68320 | 0.55890 | −0.00570 | 0.0590* | |
| H15 | −0.02670 | 0.57600 | 0.11020 | 0.0530* | |
| H16A | −0.07880 | 0.43040 | 0.10190 | 0.0660* | |
| H16B | −0.02830 | 0.41250 | 0.01470 | 0.0660* | |
| H17A | 0.14400 | 0.37250 | 0.20020 | 0.0780* | |
| H17B | 0.39400 | 0.38830 | 0.16900 | 0.0780* | |
| H18A | 0.29390 | 0.25340 | 0.23750 | 0.0950* | |
| H18B | 0.48580 | 0.25600 | 0.17360 | 0.0950* | |
| H19A | 0.27120 | 0.17710 | 0.10100 | 0.1130* | |
| H19B | 0.07160 | 0.18070 | 0.16200 | 0.1130* | |
| H20A | 0.04430 | 0.25260 | 0.02840 | 0.0860* | |
| H20B | −0.10750 | 0.27930 | 0.09930 | 0.0860* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0507 (9) | 0.0596 (10) | 0.1298 (18) | −0.0041 (7) | 0.0166 (10) | −0.0278 (10) |
| O2 | 0.0555 (9) | 0.0515 (8) | 0.0663 (9) | 0.0081 (7) | 0.0056 (7) | −0.0088 (7) |
| N1 | 0.0488 (9) | 0.0383 (8) | 0.0613 (10) | −0.0074 (7) | −0.0064 (8) | −0.0087 (7) |
| C1 | 0.0520 (11) | 0.0477 (10) | 0.0574 (11) | −0.0010 (9) | 0.0031 (10) | 0.0005 (9) |
| C2 | 0.0739 (15) | 0.0497 (11) | 0.0586 (12) | −0.0030 (11) | 0.0022 (11) | −0.0077 (9) |
| C3 | 0.0712 (15) | 0.0524 (11) | 0.0593 (12) | −0.0158 (11) | −0.0055 (11) | −0.0015 (10) |
| C4 | 0.0575 (13) | 0.0671 (13) | 0.0559 (11) | −0.0157 (11) | 0.0028 (10) | 0.0035 (10) |
| C5 | 0.0567 (12) | 0.0548 (11) | 0.0488 (10) | −0.0026 (9) | 0.0032 (9) | −0.0034 (8) |
| C6 | 0.0480 (10) | 0.0419 (9) | 0.0431 (9) | 0.0014 (8) | −0.0052 (7) | 0.0033 (7) |
| C7 | 0.0475 (10) | 0.0472 (10) | 0.0547 (10) | −0.0015 (8) | −0.0001 (8) | 0.0017 (8) |
| C8 | 0.0485 (11) | 0.0450 (10) | 0.0598 (11) | −0.0021 (8) | 0.0000 (9) | −0.0025 (8) |
| C9 | 0.0444 (10) | 0.0447 (10) | 0.0607 (11) | −0.0001 (8) | −0.0013 (9) | −0.0034 (8) |
| C10 | 0.0427 (9) | 0.0421 (9) | 0.0446 (9) | 0.0006 (8) | −0.0046 (7) | 0.0001 (7) |
| C11 | 0.0442 (9) | 0.0466 (10) | 0.0490 (10) | −0.0057 (8) | 0.0012 (8) | 0.0048 (8) |
| C12 | 0.0407 (9) | 0.0584 (11) | 0.0493 (10) | 0.0036 (9) | 0.0068 (8) | 0.0028 (8) |
| C13 | 0.0434 (10) | 0.0459 (9) | 0.0431 (8) | 0.0052 (8) | −0.0032 (8) | −0.0026 (7) |
| C14 | 0.0388 (9) | 0.0432 (9) | 0.0478 (9) | −0.0009 (7) | −0.0065 (8) | −0.0035 (7) |
| C15 | 0.0339 (8) | 0.0475 (9) | 0.0510 (9) | 0.0004 (7) | 0.0005 (7) | −0.0029 (8) |
| C16 | 0.0424 (10) | 0.0486 (10) | 0.0741 (13) | −0.0049 (9) | −0.0064 (9) | −0.0110 (10) |
| C17 | 0.0794 (16) | 0.0539 (12) | 0.0610 (12) | −0.0079 (12) | −0.0102 (12) | −0.0087 (10) |
| C18 | 0.100 (2) | 0.0572 (13) | 0.0788 (16) | −0.0084 (14) | −0.0123 (17) | 0.0062 (12) |
| C19 | 0.129 (3) | 0.0513 (13) | 0.102 (2) | −0.0247 (16) | −0.024 (2) | 0.0075 (14) |
| C20 | 0.0704 (15) | 0.0492 (12) | 0.0960 (19) | −0.0208 (11) | −0.0125 (14) | −0.0097 (12) |
Geometric parameters (Å, º)
| O1—C9 | 1.224 (3) | C17—C18 | 1.503 (3) |
| O2—C13 | 1.352 (2) | C18—C19 | 1.511 (5) |
| N1—C16 | 1.465 (3) | C19—C20 | 1.503 (4) |
| N1—C17 | 1.460 (3) | C1—H1 | 0.9300 |
| N1—C20 | 1.467 (3) | C2—H2 | 0.9300 |
| O2—H1O | 0.85 (3) | C3—H3 | 0.9300 |
| C1—C2 | 1.389 (3) | C4—H4 | 0.9300 |
| C1—C6 | 1.387 (3) | C5—H5 | 0.9300 |
| C2—C3 | 1.370 (4) | C7—H7 | 0.9300 |
| C3—C4 | 1.379 (3) | C8—H8 | 0.9300 |
| C4—C5 | 1.387 (3) | C11—H11 | 0.9300 |
| C5—C6 | 1.390 (3) | C12—H12 | 0.9300 |
| C6—C7 | 1.461 (3) | C15—H15 | 0.9300 |
| C7—C8 | 1.317 (3) | C16—H16A | 0.9700 |
| C8—C9 | 1.478 (3) | C16—H16B | 0.9700 |
| C9—C10 | 1.485 (3) | C17—H17A | 0.9700 |
| C10—C15 | 1.397 (3) | C17—H17B | 0.9700 |
| C10—C11 | 1.396 (3) | C18—H18A | 0.9700 |
| C11—C12 | 1.383 (3) | C18—H18B | 0.9700 |
| C12—C13 | 1.383 (3) | C19—H19A | 0.9700 |
| C13—C14 | 1.403 (3) | C19—H19B | 0.9700 |
| C14—C15 | 1.380 (3) | C20—H20A | 0.9700 |
| C14—C16 | 1.508 (3) | C20—H20B | 0.9700 |
| C16—N1—C17 | 113.41 (17) | C3—C4—H4 | 120.00 |
| C16—N1—C20 | 113.92 (18) | C5—C4—H4 | 120.00 |
| C17—N1—C20 | 105.22 (19) | C4—C5—H5 | 120.00 |
| C13—O2—H1O | 104 (2) | C6—C5—H5 | 120.00 |
| C2—C1—C6 | 121.5 (2) | C6—C7—H7 | 116.00 |
| C1—C2—C3 | 119.3 (2) | C8—C7—H7 | 116.00 |
| C2—C3—C4 | 120.4 (2) | C7—C8—H8 | 119.00 |
| C3—C4—C5 | 120.3 (2) | C9—C8—H8 | 119.00 |
| C4—C5—C6 | 120.27 (19) | C10—C11—H11 | 120.00 |
| C1—C6—C7 | 119.54 (18) | C12—C11—H11 | 120.00 |
| C5—C6—C7 | 122.18 (17) | C11—C12—H12 | 120.00 |
| C1—C6—C5 | 118.28 (18) | C13—C12—H12 | 120.00 |
| C6—C7—C8 | 127.9 (2) | C10—C15—H15 | 119.00 |
| C7—C8—C9 | 121.6 (2) | C14—C15—H15 | 119.00 |
| O1—C9—C8 | 120.43 (19) | N1—C16—H16A | 109.00 |
| O1—C9—C10 | 120.29 (19) | N1—C16—H16B | 109.00 |
| C8—C9—C10 | 119.27 (19) | C14—C16—H16A | 109.00 |
| C9—C10—C11 | 123.43 (17) | C14—C16—H16B | 109.00 |
| C9—C10—C15 | 118.32 (17) | H16A—C16—H16B | 108.00 |
| C11—C10—C15 | 118.24 (17) | N1—C17—H17A | 111.00 |
| C10—C11—C12 | 120.41 (19) | N1—C17—H17B | 111.00 |
| C11—C12—C13 | 120.4 (2) | C18—C17—H17A | 111.00 |
| O2—C13—C12 | 118.81 (17) | C18—C17—H17B | 111.00 |
| O2—C13—C14 | 120.68 (17) | H17A—C17—H17B | 109.00 |
| C12—C13—C14 | 120.51 (18) | C17—C18—H18A | 111.00 |
| C13—C14—C15 | 118.17 (17) | C17—C18—H18B | 111.00 |
| C13—C14—C16 | 119.78 (17) | C19—C18—H18A | 111.00 |
| C15—C14—C16 | 122.02 (17) | C19—C18—H18B | 111.00 |
| C10—C15—C14 | 122.29 (17) | H18A—C18—H18B | 109.00 |
| N1—C16—C14 | 111.35 (18) | C18—C19—H19A | 111.00 |
| N1—C17—C18 | 104.54 (19) | C18—C19—H19B | 110.00 |
| C17—C18—C19 | 105.3 (2) | C20—C19—H19A | 111.00 |
| C18—C19—C20 | 106.1 (2) | C20—C19—H19B | 111.00 |
| N1—C20—C19 | 104.9 (2) | H19A—C19—H19B | 109.00 |
| C2—C1—H1 | 119.00 | N1—C20—H20A | 111.00 |
| C6—C1—H1 | 119.00 | N1—C20—H20B | 111.00 |
| C1—C2—H2 | 120.00 | C19—C20—H20A | 111.00 |
| C3—C2—H2 | 120.00 | C19—C20—H20B | 111.00 |
| C2—C3—H3 | 120.00 | H20A—C20—H20B | 109.00 |
| C4—C3—H3 | 120.00 | ||
| C16—N1—C17—C18 | 162.8 (2) | C8—C9—C10—C11 | −14.0 (3) |
| C17—N1—C16—C14 | 67.5 (2) | C8—C9—C10—C15 | 164.78 (18) |
| C20—N1—C16—C14 | −172.2 (2) | C15—C10—C11—C12 | −0.7 (3) |
| C17—N1—C20—C19 | −34.8 (3) | C11—C10—C15—C14 | 0.7 (3) |
| C20—N1—C17—C18 | 37.6 (3) | C9—C10—C11—C12 | 178.07 (19) |
| C16—N1—C20—C19 | −159.6 (2) | C9—C10—C15—C14 | −178.13 (18) |
| C6—C1—C2—C3 | 1.4 (3) | C10—C11—C12—C13 | −0.6 (3) |
| C2—C1—C6—C5 | −2.1 (3) | C11—C12—C13—O2 | −178.20 (18) |
| C2—C1—C6—C7 | 177.4 (2) | C11—C12—C13—C14 | 1.9 (3) |
| C1—C2—C3—C4 | 0.5 (4) | C12—C13—C14—C15 | −1.9 (3) |
| C2—C3—C4—C5 | −1.6 (4) | C12—C13—C14—C16 | 176.13 (19) |
| C3—C4—C5—C6 | 0.8 (3) | O2—C13—C14—C15 | 178.24 (18) |
| C4—C5—C6—C7 | −178.5 (2) | O2—C13—C14—C16 | −3.7 (3) |
| C4—C5—C6—C1 | 1.0 (3) | C16—C14—C15—C10 | −177.39 (19) |
| C5—C6—C7—C8 | 15.6 (3) | C13—C14—C15—C10 | 0.6 (3) |
| C1—C6—C7—C8 | −163.9 (2) | C13—C14—C16—N1 | 42.4 (3) |
| C6—C7—C8—C9 | 178.1 (2) | C15—C14—C16—N1 | −139.68 (19) |
| C7—C8—C9—C10 | −174.3 (2) | N1—C17—C18—C19 | −25.5 (3) |
| C7—C8—C9—O1 | 4.3 (3) | C17—C18—C19—C20 | 4.3 (3) |
| O1—C9—C10—C15 | −13.8 (3) | C18—C19—C20—N1 | 18.3 (3) |
| O1—C9—C10—C11 | 167.5 (2) |
Hydrogen-bond geometry (Å, º)
Cg3 is the centroid of the C10–C15 ring.
| D—H···A | D—H | H···A | D···A | D—H···A |
| O2—H1O···N1 | 0.85 (3) | 1.85 (3) | 2.633 (2) | 154 (3) |
| C5—H5···Cg3i | 0.93 | 2.99 | 3.685 (2) | 132 |
Symmetry code: (i) x+1/2, −y+3/2, −z.
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989016006009/hb7576sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989016006009/hb7576Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989016006009/hb7576Isup3.cml
CCDC reference: 1473395
Additional supporting information: crystallographic information; 3D view; checkCIF report