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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 5| May 2016| Pages 696-698
doi:10.1107/S2056989016006009

Crystal structure of 1-{4-hy­dr­oxy-3-[(pyrrolidin-1-yl)meth­yl]phen­yl}-3-phenyl­prop-2-en-1-one

CROSSMARK_Color_square_no_text.svg
Abdullah Aydın,a* Mehmet Akkurt,b Halise Inci Gul,c Kadir Ozden Yerdelenc and Raziye Catak Celikd

aDepartment of Science Education, Faculty of Education, Kastamonu University, 37200 Kastamonu, Turkey, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Atatürk University, 25240 Erzurum, Turkey, and dScientific and Technological Application and Research Center, Aksaray University, 68100 Aksaray, Turkey
*Correspondence e-mail: aaydin@kastamonu.edu.tr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 April 2016; accepted 11 April 2016; online 15 April 2016)

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.

CCDC reference: 1473395

1. Chemical context

Mannich bases are a group of compounds having various biological activities such as cytotoxic (Bilginer et al., 2013[Bilginer, S., Gul, H. I., Mete, E., Das, U., Sakagami, H., Umemura, N. & Dimmock, J. R. (2013). J. Enzyme Inhib. Med. Chem. 28, 974-980.]), anti-inflammatory (Sahin et al., 2010[Sahin, Y. N., Demircan, B., Suleyman, H., Aksoy, H. & Gul, H. I. (2010). Turk. J. Med. Sci. 40, 723-728.]) and anti­convulsant (Gul et al., 2004[Gul, H. I., Calis, U. & Vepsalainen, J. (2004). Arzn. Fors. 54, 359-364.]) 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.

[Scheme 1]

The cytotoxic and anti­cancer properties of chalcone (1,3-diphenyl-2-propenone) and related compounds have been reported (Bilginer et al., 2013[Bilginer, S., Gul, H. I., Mete, E., Das, U., Sakagami, H., Umemura, N. & Dimmock, J. R. (2013). J. Enzyme Inhib. Med. Chem. 28, 974-980.]; Dimmock et al., 1998[Dimmock, J. R., Kandepu, N. M., Hetherington, M., Quail, J. W., Pugazhenthi, U., Sudom, A. M., Chamankhah, M., Rose, P., Pass, E., Allen, T. M., Halleran, S., Szydlowski, J., Mutus, B., Tannous, M., Manavathu, E. K., Myers, T. G., De Clercq, E. & Balzarini, J. (1998). J. Med. Chem. 41, 1014-1026.]; Gul Cizmecioglu et al., 2009[Gul, H. I., Cizmecioglu, M., Zencir, S., Gul, M., Canturk, P., Atalay, M. & Topcu, Z. (2009). J. Enzyme Inhib. Med. Chem. 24, 804-807.]); Gul Mete et al., 2009[Gul, M., Mete, E., Atalay, M., Arik, M. & Gul, H. I. (2009). Arzn. Fors. Drug. Res. , 59, 364-369.]). The title compound, (I)[link], reported in this study is a Mannich base of phenolic chalcone.

2. Structural commentary

In the title compound (Fig. 1[link]), 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)[link] are comparable those reported for related compounds (Suhud et al., 2015[Suhud, K., Heng, L. Y., Hasbullah, S. A., Ahmad, M. & Kassim, M. B. (2015). Acta Cryst. E71, o225-o226.]; Palakshamurthy et al., 2012[Palakshamurthy, B. S., Srinivasa, H. T., Kumar, V., Sreenivasa, S. & Devarajegowda, H. C. (2012). Acta Cryst. E68, o3382.]). An intra­molecular O2—H1O⋯N1 hydrogen bond (Table 1[link], Fig. 2[link]) helps to establish the mol­ecular conformation of (I)[link].

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) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].
[Figure 1]
Figure 1
View of the mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2]
Figure 2
The mol­ecular packing and hydrogen bonding viewed down the a axis.

3. Supra­molecular features

The only directional inter­action present in the crystal of (I)[link] is a very weak C—H⋯π bond (Table 1[link]).

4. 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[Pople, J. A. & Beveridge, D. L. (1970). In Approximate Molecular Orbital Theory. New York: McGraw-Hill.]). The spatial view of the single mol­ecule, with atomic labels, calculated as a closed-shell in a vacuum is shown in Fig. 3[link]. 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]
Figure 3
The conformation of the title compound, calculated using the CNDO method.

5. Biological activity

Compound (I)[link] 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[Yerdelen, K. O. (2009). PhD thesis, Health Sciences, Atatürk University, Erzurum, Turkey.]).

6. 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[Yerdelen, K. O. (2009). PhD thesis, Health Sciences, Atatürk University, Erzurum, Turkey.]).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. 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 Uiso(H) = 1.2Ueq(C). The hydroxyl H atom was found from a difference Fourier map and its positional parameters were freely refined with Uiso(H) = 1.5Ueq(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
Mr 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[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.951, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections 37526, 4120, 3647
Rint 0.050
(sin θ/λ)max (Å−1) 0.668
 
Refinement
R[F2 > 2σ(F2)], wR(F2), 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
Computer programs: APEX2 and SAINT (Bruker, 2007[Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC reference: 1473395

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989016006009/hb7576sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989016006009/hb7576Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989016006009/hb7576Isup3.cml

checkCIF report


Chemical context top

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 top

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).

Supra­molecular features top

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 top

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.

Biological activity top

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 top

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 contents of reaction was monitored by thin layer chromatography (TLC). The reaction was 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).

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 top

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 Uiso(H) = 1.2Ueq(C). The hydroxyl H atom was found from difference Fourier maps and its positional parameters were freely refined with Uiso(H) = 1.5Ueq(O). The 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 owing to bad disagreement. The Flack absolute structure parameter was found to be indeterminate in the present study.

Structure description top

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.

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).

The only directional inter­action present in the crystal of (I) is a very weak C—H···π bond (Table 1).

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.

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 top

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 contents of reaction was monitored by thin layer chromatography (TLC). The reaction was 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).

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 details top

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 Uiso(H) = 1.2Ueq(C). The hydroxyl H atom was found from difference Fourier maps and its positional parameters were freely refined with Uiso(H) = 1.5Ueq(O). The 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 owing to bad disagreement. The Flack absolute structure parameter was found to be indeterminate in the present study.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing and hydrogen bonding viewed down the a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.
[Figure 3] Fig. 3. The conformation of the title compound calculated, calculated using the CNDO method.
1-{4-Hydroxy-3-[(pyrrolidin-1-yl)methyl]phenyl}-3-phenylprop-2-en-1-one top
Crystal data top
C20H21NO2F(000) = 656
Mr = 307.38Dx = 1.234 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4120 reflections
a = 5.8403 (5) Åθ = 2.4–27.7°
b = 16.3195 (13) ŵ = 0.08 mm−1
c = 17.3615 (14) ÅT = 296 K
V = 1654.7 (2) Å3Prism, light yellow
Z = 40.66 × 0.53 × 0.33 mm
Data collection top
Bruker APEXII CCD
diffractometer		4120 independent reflections
Radiation source: sealed tube3647 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 28.4°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		h = −7→7
Tmin = 0.951, Tmax = 0.974k = −21→21
37526 measured reflectionsl = −23→23
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H 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 reflectionsΔρmax = 0.24 e Å−3
211 parametersΔρmin = −0.12 e Å−3
Crystal data top
C20H21NO2V = 1654.7 (2) Å3
Mr = 307.38Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 5.8403 (5) ŵ = 0.08 mm−1
b = 16.3195 (13) ÅT = 296 K
c = 17.3615 (14) Å0.66 × 0.53 × 0.33 mm
Data collection top
Bruker APEXII CCD
diffractometer		4120 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2007)		3647 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.974Rint = 0.050
37526 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.24 e Å−3
4120 reflectionsΔρmin = −0.12 e Å−3
211 parameters
Special details top

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) top
xyzUiso*/Ueq
O1−0.0436 (3)0.72582 (11)0.13185 (14)0.0800 (7)
O20.4920 (3)0.42033 (9)0.00124 (10)0.0578 (5)
N10.1759 (3)0.34948 (10)0.08639 (10)0.0495 (5)
C10.3003 (4)0.98751 (12)0.23067 (13)0.0524 (6)
C20.4274 (5)1.05592 (14)0.25148 (13)0.0607 (7)
C30.6363 (4)1.06897 (14)0.21774 (14)0.0610 (7)
C40.7188 (4)1.01504 (15)0.16329 (13)0.0602 (7)
C50.5935 (4)0.94596 (13)0.14348 (12)0.0534 (6)
C60.3823 (3)0.93109 (11)0.17767 (10)0.0443 (5)
C70.2469 (4)0.85825 (12)0.15995 (12)0.0498 (6)
C80.3149 (4)0.79067 (12)0.12533 (12)0.0511 (6)
C90.1583 (4)0.72064 (12)0.11351 (13)0.0499 (6)
C100.2497 (3)0.64318 (11)0.08086 (10)0.0431 (5)
C110.4636 (4)0.63705 (12)0.04543 (11)0.0466 (6)
C120.5411 (4)0.56234 (13)0.01826 (11)0.0495 (6)
C130.4084 (3)0.49271 (12)0.02654 (11)0.0441 (5)
C140.1907 (3)0.49728 (11)0.06048 (11)0.0433 (5)
C150.1167 (3)0.57238 (12)0.08719 (11)0.0441 (5)
C160.0423 (4)0.42179 (13)0.06449 (14)0.0550 (6)
C170.2614 (5)0.35266 (14)0.16535 (14)0.0648 (8)
C180.3247 (6)0.26561 (15)0.18383 (17)0.0787 (10)
C190.1771 (7)0.21350 (17)0.1318 (2)0.0941 (13)
C200.0483 (5)0.27222 (14)0.08114 (18)0.0719 (9)
H10.157000.979300.252700.0630*
H1O0.418 (6)0.3850 (16)0.0268 (18)0.0870*
H20.371301.092500.288000.0730*
H30.722801.114500.231600.0730*
H40.859101.025000.139700.0720*
H50.651100.909500.107200.0640*
H70.094100.859800.174900.0600*
H80.465100.786900.107900.0610*
H110.554500.683500.040100.0560*
H120.683200.55890−0.005700.0590*
H15−0.026700.576000.110200.0530*
H16A−0.078800.430400.101900.0660*
H16B−0.028300.412500.014700.0660*
H17A0.144000.372500.200200.0780*
H17B0.394000.388300.169000.0780*
H18A0.293900.253400.237500.0950*
H18B0.485800.256000.173600.0950*
H19A0.271200.177100.101000.1130*
H19B0.071600.180700.162000.1130*
H20A0.044300.252600.028400.0860*
H20B−0.107500.279300.099300.0860*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0507 (9)0.0596 (10)0.1298 (18)−0.0041 (7)0.0166 (10)−0.0278 (10)
O20.0555 (9)0.0515 (8)0.0663 (9)0.0081 (7)0.0056 (7)−0.0088 (7)
N10.0488 (9)0.0383 (8)0.0613 (10)−0.0074 (7)−0.0064 (8)−0.0087 (7)
C10.0520 (11)0.0477 (10)0.0574 (11)−0.0010 (9)0.0031 (10)0.0005 (9)
C20.0739 (15)0.0497 (11)0.0586 (12)−0.0030 (11)0.0022 (11)−0.0077 (9)
C30.0712 (15)0.0524 (11)0.0593 (12)−0.0158 (11)−0.0055 (11)−0.0015 (10)
C40.0575 (13)0.0671 (13)0.0559 (11)−0.0157 (11)0.0028 (10)0.0035 (10)
C50.0567 (12)0.0548 (11)0.0488 (10)−0.0026 (9)0.0032 (9)−0.0034 (8)
C60.0480 (10)0.0419 (9)0.0431 (9)0.0014 (8)−0.0052 (7)0.0033 (7)
C70.0475 (10)0.0472 (10)0.0547 (10)−0.0015 (8)−0.0001 (8)0.0017 (8)
C80.0485 (11)0.0450 (10)0.0598 (11)−0.0021 (8)0.0000 (9)−0.0025 (8)
C90.0444 (10)0.0447 (10)0.0607 (11)−0.0001 (8)−0.0013 (9)−0.0034 (8)
C100.0427 (9)0.0421 (9)0.0446 (9)0.0006 (8)−0.0046 (7)0.0001 (7)
C110.0442 (9)0.0466 (10)0.0490 (10)−0.0057 (8)0.0012 (8)0.0048 (8)
C120.0407 (9)0.0584 (11)0.0493 (10)0.0036 (9)0.0068 (8)0.0028 (8)
C130.0434 (10)0.0459 (9)0.0431 (8)0.0052 (8)−0.0032 (8)−0.0026 (7)
C140.0388 (9)0.0432 (9)0.0478 (9)−0.0009 (7)−0.0065 (8)−0.0035 (7)
C150.0339 (8)0.0475 (9)0.0510 (9)0.0004 (7)0.0005 (7)−0.0029 (8)
C160.0424 (10)0.0486 (10)0.0741 (13)−0.0049 (9)−0.0064 (9)−0.0110 (10)
C170.0794 (16)0.0539 (12)0.0610 (12)−0.0079 (12)−0.0102 (12)−0.0087 (10)
C180.100 (2)0.0572 (13)0.0788 (16)−0.0084 (14)−0.0123 (17)0.0062 (12)
C190.129 (3)0.0513 (13)0.102 (2)−0.0247 (16)−0.024 (2)0.0075 (14)
C200.0704 (15)0.0492 (12)0.0960 (19)−0.0208 (11)−0.0125 (14)−0.0097 (12)
Geometric parameters (Å, º) top
O1—C91.224 (3)C17—C181.503 (3)
O2—C131.352 (2)C18—C191.511 (5)
N1—C161.465 (3)C19—C201.503 (4)
N1—C171.460 (3)C1—H10.9300
N1—C201.467 (3)C2—H20.9300
O2—H1O0.85 (3)C3—H30.9300
C1—C21.389 (3)C4—H40.9300
C1—C61.387 (3)C5—H50.9300
C2—C31.370 (4)C7—H70.9300
C3—C41.379 (3)C8—H80.9300
C4—C51.387 (3)C11—H110.9300
C5—C61.390 (3)C12—H120.9300
C6—C71.461 (3)C15—H150.9300
C7—C81.317 (3)C16—H16A0.9700
C8—C91.478 (3)C16—H16B0.9700
C9—C101.485 (3)C17—H17A0.9700
C10—C151.397 (3)C17—H17B0.9700
C10—C111.396 (3)C18—H18A0.9700
C11—C121.383 (3)C18—H18B0.9700
C12—C131.383 (3)C19—H19A0.9700
C13—C141.403 (3)C19—H19B0.9700
C14—C151.380 (3)C20—H20A0.9700
C14—C161.508 (3)C20—H20B0.9700
C16—N1—C17113.41 (17)C3—C4—H4120.00
C16—N1—C20113.92 (18)C5—C4—H4120.00
C17—N1—C20105.22 (19)C4—C5—H5120.00
C13—O2—H1O104 (2)C6—C5—H5120.00
C2—C1—C6121.5 (2)C6—C7—H7116.00
C1—C2—C3119.3 (2)C8—C7—H7116.00
C2—C3—C4120.4 (2)C7—C8—H8119.00
C3—C4—C5120.3 (2)C9—C8—H8119.00
C4—C5—C6120.27 (19)C10—C11—H11120.00
C1—C6—C7119.54 (18)C12—C11—H11120.00
C5—C6—C7122.18 (17)C11—C12—H12120.00
C1—C6—C5118.28 (18)C13—C12—H12120.00
C6—C7—C8127.9 (2)C10—C15—H15119.00
C7—C8—C9121.6 (2)C14—C15—H15119.00
O1—C9—C8120.43 (19)N1—C16—H16A109.00
O1—C9—C10120.29 (19)N1—C16—H16B109.00
C8—C9—C10119.27 (19)C14—C16—H16A109.00
C9—C10—C11123.43 (17)C14—C16—H16B109.00
C9—C10—C15118.32 (17)H16A—C16—H16B108.00
C11—C10—C15118.24 (17)N1—C17—H17A111.00
C10—C11—C12120.41 (19)N1—C17—H17B111.00
C11—C12—C13120.4 (2)C18—C17—H17A111.00
O2—C13—C12118.81 (17)C18—C17—H17B111.00
O2—C13—C14120.68 (17)H17A—C17—H17B109.00
C12—C13—C14120.51 (18)C17—C18—H18A111.00
C13—C14—C15118.17 (17)C17—C18—H18B111.00
C13—C14—C16119.78 (17)C19—C18—H18A111.00
C15—C14—C16122.02 (17)C19—C18—H18B111.00
C10—C15—C14122.29 (17)H18A—C18—H18B109.00
N1—C16—C14111.35 (18)C18—C19—H19A111.00
N1—C17—C18104.54 (19)C18—C19—H19B110.00
C17—C18—C19105.3 (2)C20—C19—H19A111.00
C18—C19—C20106.1 (2)C20—C19—H19B111.00
N1—C20—C19104.9 (2)H19A—C19—H19B109.00
C2—C1—H1119.00N1—C20—H20A111.00
C6—C1—H1119.00N1—C20—H20B111.00
C1—C2—H2120.00C19—C20—H20A111.00
C3—C2—H2120.00C19—C20—H20B111.00
C2—C3—H3120.00H20A—C20—H20B109.00
C4—C3—H3120.00
C16—N1—C17—C18162.8 (2)C8—C9—C10—C11−14.0 (3)
C17—N1—C16—C1467.5 (2)C8—C9—C10—C15164.78 (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—C140.7 (3)
C20—N1—C17—C1837.6 (3)C9—C10—C11—C12178.07 (19)
C16—N1—C20—C19−159.6 (2)C9—C10—C15—C14−178.13 (18)
C6—C1—C2—C31.4 (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—C7177.4 (2)C11—C12—C13—C141.9 (3)
C1—C2—C3—C40.5 (4)C12—C13—C14—C15−1.9 (3)
C2—C3—C4—C5−1.6 (4)C12—C13—C14—C16176.13 (19)
C3—C4—C5—C60.8 (3)O2—C13—C14—C15178.24 (18)
C4—C5—C6—C7−178.5 (2)O2—C13—C14—C16−3.7 (3)
C4—C5—C6—C11.0 (3)C16—C14—C15—C10−177.39 (19)
C5—C6—C7—C815.6 (3)C13—C14—C15—C100.6 (3)
C1—C6—C7—C8−163.9 (2)C13—C14—C16—N142.4 (3)
C6—C7—C8—C9178.1 (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—O14.3 (3)C17—C18—C19—C204.3 (3)
O1—C9—C10—C15−13.8 (3)C18—C19—C20—N118.3 (3)
O1—C9—C10—C11167.5 (2)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
O2—H1O···N10.85 (3)1.85 (3)2.633 (2)154 (3)
C5—H5···Cg3i0.932.993.685 (2)132
Symmetry code: (i) x+1/2, −y+3/2, −z.
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the C10–C15 ring.
D—H···AD—HH···AD···AD—H···A
O2—H1O···N10.85 (3)1.85 (3)2.633 (2)154 (3)
C5—H5···Cg3i0.932.993.685 (2)132
Symmetry code: (i) x+1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formulaC20H21NO2
Mr307.38
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)5.8403 (5), 16.3195 (13), 17.3615 (14)
V (Å3)1654.7 (2)
Z4
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.66 × 0.53 × 0.33
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2007)
Tmin, Tmax0.951, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections		37526, 4120, 3647
Rint0.050
(sin θ/λ)max (Å−1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.118, 1.03
No. of reflections4120
No. of parameters211
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.24, −0.12

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

 

Acknowledgements

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)

References

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 5| May 2016| Pages 696-698
doi:10.1107/S2056989016006009
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