2-(4-Meth­oxy-2-methyl­anilino)-1,2-diphenyl­ethanone

Arslan, H.; Algul, O.; Zirek, S.; Tari, O.; Demircan, A.; Hardcastle, K.I.

doi:10.1107/S1600536811015960

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1303

doi:10.1107/S1600536811015960

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2-(4-Methoxy-2-methylanilino)-1,2-diphenylethanone

Hakan Arslan,^a,^b ^* Oztekin Algul,^c Selin Zirek,^c Ozden Tari,^c Aydın Demircan ^d and Kenneth I. Hardcastle ^a

^aDepartment of Chemistry, Emory University, Atlanta, GA 30322, USA, ^bDepartment of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey, ^cDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Mersin University, Mersin, TR 33169, Turkey, and ^dDepartment of Chemistry, Faculty of Arts and Sciences, Nigde University, Nigde, TR 51240, Turkey
^*Correspondence e-mail: hakan.arslan.acad@gmail.com

(Received 26 April 2011; accepted 27 April 2011; online 7 May 2011)

The title compound, C₂₂H₂₁NO₂, was synthesized from 4-methoxy-2-methylaniline and 2-hydroxy-1,2-diphenylethanone. In the title compound, the C—C—C—N—C backbone adopts an all-trans conformation. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen-bond interactions.

Related literature

For the synthesis and similar structures, see: Au & Tafeenko (1986 , 1987 ); Batsanov et al., (2006 ). For general background to these structures, see: Batsanov et al. (2006); Abdulla et al. (1985 ). For bond-length data, see: Allen et al. (1987 ). For geometrical analysis, see: Bruno et al. (2002 ).

Experimental

Crystal data

C₂₂H₂₁NO₂
M_r = 331.40
Monoclinic, P 2₁ /c
a = 12.570 (12) Å
b = 8.009 (8) Å
c = 18.091 (17) Å
β = 100.544 (15)°
V = 1791 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 K
0.21 × 0.19 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.984, T_max = 0.988
28799 measured reflections
4122 independent reflections
2935 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.112
S = 1.05
4122 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O1ⁱ	0.95	2.48	3.352 (4)	153
Symmetry code: (i) x, y+1, z.

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2, publCIF (Westrip, 2010 ) and Mercury (Macrae et al., 2006 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015960/hg5030sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015960/hg5030Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015960/hg5030Isup3.cml

checkCIF report

Comment top

A few 1-arylanilinoethanone derivatives have been structurally charactized because of their importance in synthesis or because of their interesting charge-transfer properties (Abdulla et al., 1985). We found only four structurally similar compounds (Au & Tafeenko, 1987; Au & Tafeenko, 1986; Batsanov et al., 2006) in the Cambridge Structural Database (CSD CONQUEST 1.11, B4; Bruno et al., 2002).

Compound I was synthesized by the HCl acid-catalyzed reaction of a benzoin derivative to 4-methoxy-2-methylaniline (Scheme 1) resulting in the title compound, 2-((4-methoxy-2-methylphenyl)amino)-1,2-diphenylethanone, I, Figure 1, its structure was determined by X-ray crystallography.

The molecular structure of the title compound contains two phenyl rings and one substituted aniline ring connected by a –C(O)—C– linker. The dihedral angle between the two phenyl rings is 87.78 (7) ° and the dihedral angle between the substitute aniline and phenyl rings are 55.30 (7) and 84.57 (7) °, respectively. In adition, in the title compound, the C2—C1—C8—N1—C15 backbone adopts an all-trans conformation (Au & Tafeenko, 1987; Au & Tafeenko, 1986; Batsanov et al., 2006).

The C—N bond lengths C8—N1 and C15—N1 are shorter than the normal C—N single-bond length of about 1.48 Å. The shortening of these C—N bonds reveals the effects of some conjugation in this part of the molecule. All other bond lengths fall within the expected ranges (Allen et al., 1987).

Intramolecular hydrogen bonding N1–H1A···O1 with N–H 0.88 Å, H···O 2.22 Å, N–H···O 107 ° results in the formation of a five membered ring in the O1—C1—C8—N1–H1A plane. The crystal packing is dominated by weak intermolecular C11—H11A···O1 (x, 1 + y, z) hydrogen bonds, with H···O = 2.48 Å and a C—H···O angle of 153 ° (Figure 2).

Related literature top

For the synthesis and similar structures, see: Au & Tafeenko (1986, 1987); Batsanov et al., (2006). For general background to these structures, see: Batsanov et al. (2006); Abdulla et al. (1985). For bond-length data, see: Allen et al. (1987). For geometrical analysis, see: Bruno et al. (2002).

Experimental top

A mixture of 4-methoxy-2-methylaniline (15 mmol), 2-hydroxy-1,2-diphenylethanone (5 mmol) and 1 ml conc. HCl in 20 ml of ethanol were refluxed for 5 h (Figure 3). After reaction was complete, the mixture was allowed to cool to room temperature, poured into cold water (20 ml) and finally extracted with CH₂Cl₂ (3x15 ml). The organic layer was dried over magnesium sulfate and the solvent removed under reduced pressure to yield a crude product that was purified by recrystallization in ethyl acetate. 2-((4-methoxy-2-methylphenyl)amino)-1,2-diphenylethanone: Yield: 1.20 g, 46%. M.p.: 110–112 °C. ¹H NMR (DMSO-d₆) δ: 8.18–8.16 (d, 2H, Ar—H (C3, C7)), 7.62 (t, 1H, Ar—H (C5)), 7.56–7.49 (m, 4H, Ar—H (C4, C6, C11, C13)), 7.30–7.26 (m, 2H, Ar—H (C10, C14)), 7.16 (t, 1H, Ar—H (C12)), 6.70–6.68 (d, J=4.8 Hz, 1H, Ar—H (C19)), 6.67 (s, 1H, Ar—H (C17)), 6.57–6.55 (d, J=8 Hz, 1H, Ar—H (C20)), 6.46–6.44 (d, J=8 Hz, 1H, Ar—H (C8)), 5.19–5.17 (d, J=8 Hz, 1H, NH), 3.60 (s, 3H, OCH₃), 2.22 (s, 3H, CH₃). ¹³C NMR (400 MHz, p.p.m.) δ: 17.5 (CH₃), 55.1 (OCH₃), 61.5 (C8), 111.2 (C19), 112.5 (C20), 116.4 (C17), 123.9 (C16), 127.6, 128.1, 128.6, 128.7, 128.8 (C), 133.7 (C5), 134.7 (C2), 138.1 (C9), 138.3 (C15), 151.1 (C18), 197.6 (C9). Anal. Calc. for C₂₂H₂₁NO₂: C, 79.73; H, 6.39; N, 4.23%. Found: C, 79.70; H, 6.21; N, 4.19%.

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. The molecular structure of (I), showing ellipsoids at the 50% probability level.
	Fig. 2. The molecular packing of (I). The hydrogen bonds are shown as dashed lines.
	Fig. 3. Synthesis of the title compound.

2-(4-Methoxy-2-methylanilino)-1,2-diphenylethanone top

Crystal data top

C₂₂H₂₁NO₂	F(000) = 704
M_r = 331.40	D_x = 1.229 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4852 reflections
a = 12.570 (12) Å	θ = 2.3–24.5°
b = 8.009 (8) Å	µ = 0.08 mm⁻¹
c = 18.091 (17) Å	T = 173 K
β = 100.544 (15)°	Block, yellow
V = 1791 (3) Å³	0.21 × 0.19 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4122 independent reflections
Radiation source: fine-focus sealed tube	2935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.984, T_max = 0.988	k = −10→10
28799 measured reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0413P)² + 0.4229P] where P = (F_o² + 2F_c²)/3
4122 reflections	(Δ/σ)_max = 0.004
226 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₂H₂₁NO₂	V = 1791 (3) Å³
M_r = 331.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.570 (12) Å	µ = 0.08 mm⁻¹
b = 8.009 (8) Å	T = 173 K
c = 18.091 (17) Å	0.21 × 0.19 × 0.15 mm
β = 100.544 (15)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4122 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2935 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.988	R_int = 0.055
28799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.05	Δρ_max = 0.27 e Å⁻³
4122 reflections	Δρ_min = −0.25 e Å⁻³
226 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	0.70413 (11)	0.71666 (18)	0.13255 (8)	0.0336 (3)
C2	0.65511 (11)	0.79413 (17)	0.05905 (7)	0.0314 (3)
C3	0.70228 (12)	0.92642 (19)	0.02686 (8)	0.0380 (3)
H3A	0.7667	0.9764	0.0533	0.046*
C4	0.65510 (14)	0.9856 (2)	−0.04399 (8)	0.0453 (4)
H4A	0.6879	1.0748	−0.0662	0.054*
C5	0.56034 (14)	0.9144 (2)	−0.08206 (8)	0.0436 (4)
H5A	0.5286	0.9546	−0.1305	0.052*
C6	0.51179 (13)	0.7853 (2)	−0.05009 (8)	0.0420 (4)
H6A	0.4460	0.7385	−0.0761	0.050*
C7	0.55897 (12)	0.72392 (18)	0.01989 (8)	0.0361 (3)
H7A	0.5260	0.6339	0.0414	0.043*
C8	0.78651 (11)	0.81396 (18)	0.19059 (8)	0.0339 (3)
H8A	0.8385	0.8744	0.1644	0.041*
C9	0.72052 (11)	0.94044 (17)	0.22728 (7)	0.0297 (3)
C10	0.72302 (12)	1.11045 (18)	0.21167 (8)	0.0370 (3)
H10A	0.7685	1.1508	0.1790	0.044*
C11	0.65930 (13)	1.22179 (18)	0.24361 (9)	0.0421 (4)
H11A	0.6615	1.3376	0.2327	0.051*
C12	0.59250 (12)	1.16418 (19)	0.29135 (8)	0.0396 (4)
H12A	0.5489	1.2403	0.3129	0.048*
C13	0.58976 (12)	0.99566 (19)	0.30736 (8)	0.0378 (3)
H13A	0.5441	0.9557	0.3399	0.045*
C14	0.65372 (11)	0.88458 (18)	0.27584 (8)	0.0334 (3)
H14A	0.6519	0.7691	0.2875	0.040*
C15	0.91952 (11)	0.72896 (19)	0.30593 (8)	0.0330 (3)
C16	0.95263 (11)	0.59902 (19)	0.35825 (8)	0.0346 (3)
C17	1.02943 (11)	0.6351 (2)	0.42183 (8)	0.0393 (4)
H17A	1.0524	0.5485	0.4570	0.047*
C18	1.07393 (12)	0.7936 (2)	0.43580 (8)	0.0412 (4)
C19	1.04216 (12)	0.9204 (2)	0.38448 (8)	0.0409 (4)
H19A	1.0725	1.0289	0.3929	0.049*
C20	0.96492 (11)	0.88712 (19)	0.32004 (8)	0.0375 (3)
H20A	0.9429	0.9745	0.2851	0.045*
C21	0.90500 (13)	0.4262 (2)	0.34587 (9)	0.0442 (4)
H21A	0.9374	0.3535	0.3875	0.066*
H21B	0.9201	0.3810	0.2985	0.066*
H21C	0.8266	0.4318	0.3435	0.066*
C22	1.19345 (16)	0.9696 (3)	0.52047 (11)	0.0690 (6)
H22A	1.2440	0.9640	0.5686	0.103*
H22B	1.1358	1.0496	0.5244	0.103*
H22C	1.2322	1.0058	0.4810	0.103*
N1	0.84386 (10)	0.69119 (16)	0.24129 (7)	0.0412 (3)
H1A	0.8302	0.5852	0.2308	0.049*
O1	0.67637 (9)	0.57676 (13)	0.14827 (6)	0.0477 (3)
O2	1.14758 (10)	0.80923 (17)	0.50230 (6)	0.0612 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0331 (7)	0.0372 (8)	0.0294 (7)	−0.0008 (6)	0.0026 (6)	−0.0002 (6)
C2	0.0323 (7)	0.0345 (8)	0.0264 (7)	0.0029 (6)	0.0024 (6)	−0.0041 (6)
C3	0.0388 (8)	0.0420 (8)	0.0318 (8)	−0.0004 (7)	0.0030 (6)	−0.0009 (6)
C4	0.0585 (10)	0.0449 (9)	0.0338 (8)	0.0049 (8)	0.0114 (7)	0.0045 (7)
C5	0.0558 (10)	0.0458 (9)	0.0256 (7)	0.0141 (8)	−0.0022 (7)	−0.0025 (6)
C6	0.0435 (9)	0.0450 (9)	0.0326 (8)	0.0067 (7)	−0.0062 (7)	−0.0089 (7)
C7	0.0386 (8)	0.0360 (8)	0.0318 (7)	0.0014 (6)	0.0013 (6)	−0.0056 (6)
C8	0.0314 (7)	0.0377 (8)	0.0299 (7)	−0.0001 (6)	−0.0013 (6)	0.0027 (6)
C9	0.0279 (7)	0.0321 (7)	0.0252 (7)	−0.0033 (6)	−0.0055 (5)	0.0023 (5)
C10	0.0399 (8)	0.0347 (8)	0.0331 (7)	−0.0082 (6)	−0.0024 (6)	0.0067 (6)
C11	0.0503 (9)	0.0265 (7)	0.0418 (8)	−0.0024 (7)	−0.0121 (7)	0.0012 (6)
C12	0.0401 (8)	0.0371 (8)	0.0362 (8)	0.0056 (7)	−0.0076 (7)	−0.0060 (6)
C13	0.0381 (8)	0.0399 (8)	0.0337 (7)	−0.0025 (7)	0.0023 (6)	−0.0008 (6)
C14	0.0373 (8)	0.0288 (7)	0.0314 (7)	−0.0032 (6)	−0.0006 (6)	0.0029 (6)
C15	0.0260 (7)	0.0444 (8)	0.0281 (7)	0.0042 (6)	0.0033 (5)	0.0017 (6)
C16	0.0279 (7)	0.0453 (9)	0.0315 (7)	0.0023 (6)	0.0084 (6)	0.0050 (6)
C17	0.0302 (7)	0.0542 (10)	0.0333 (8)	0.0001 (7)	0.0047 (6)	0.0151 (7)
C18	0.0297 (8)	0.0616 (10)	0.0295 (7)	−0.0071 (7)	−0.0016 (6)	0.0101 (7)
C19	0.0351 (8)	0.0499 (9)	0.0356 (8)	−0.0089 (7)	0.0011 (6)	0.0052 (7)
C20	0.0337 (8)	0.0445 (9)	0.0323 (7)	0.0018 (7)	0.0007 (6)	0.0082 (6)
C21	0.0437 (9)	0.0476 (9)	0.0407 (8)	−0.0011 (7)	0.0062 (7)	0.0079 (7)
C22	0.0614 (12)	0.0892 (15)	0.0463 (10)	−0.0308 (11)	−0.0170 (9)	0.0086 (10)
N1	0.0441 (7)	0.0359 (7)	0.0371 (7)	0.0081 (6)	−0.0094 (6)	−0.0035 (5)
O1	0.0572 (7)	0.0424 (6)	0.0380 (6)	−0.0124 (5)	−0.0057 (5)	0.0068 (5)
O2	0.0565 (7)	0.0759 (9)	0.0411 (6)	−0.0243 (7)	−0.0179 (6)	0.0195 (6)

Geometric parameters (Å, º) top

C1—O1	1.2226 (19)	C12—H12A	0.9500
C1—C2	1.494 (2)	C13—C14	1.390 (2)
C1—C8	1.544 (2)	C13—H13A	0.9500
C2—C3	1.393 (2)	C14—H14A	0.9500
C2—C7	1.402 (2)	C15—C20	1.394 (2)
C3—C4	1.393 (2)	C15—N1	1.399 (2)
C3—H3A	0.9500	C15—C16	1.417 (2)
C4—C5	1.385 (2)	C16—C17	1.390 (2)
C4—H4A	0.9500	C16—C21	1.509 (2)
C5—C6	1.380 (2)	C17—C18	1.391 (2)
C5—H5A	0.9500	C17—H17A	0.9500
C6—C7	1.386 (2)	C18—O2	1.383 (2)
C6—H6A	0.9500	C18—C19	1.385 (2)
C7—H7A	0.9500	C19—C20	1.399 (2)
C8—N1	1.4443 (19)	C19—H19A	0.9500
C8—C9	1.535 (2)	C20—H20A	0.9500
C8—H8A	1.0000	C21—H21A	0.9800
C9—C10	1.392 (2)	C21—H21B	0.9800
C9—C14	1.395 (2)	C21—H21C	0.9800
C10—C11	1.393 (2)	C22—O2	1.422 (2)
C10—H10A	0.9500	C22—H22A	0.9800
C11—C12	1.389 (2)	C22—H22B	0.9800
C11—H11A	0.9500	C22—H22C	0.9800
C12—C13	1.382 (2)	N1—H1A	0.8800

O1—C1—C2	119.92 (13)	C12—C13—H13A	120.0
O1—C1—C8	119.27 (13)	C14—C13—H13A	120.0
C2—C1—C8	120.77 (13)	C13—C14—C9	120.87 (14)
C3—C2—C7	119.18 (14)	C13—C14—H14A	119.6
C3—C2—C1	123.38 (13)	C9—C14—H14A	119.6
C7—C2—C1	117.39 (13)	C20—C15—N1	122.87 (13)
C2—C3—C4	120.09 (15)	C20—C15—C16	119.00 (14)
C2—C3—H3A	120.0	N1—C15—C16	118.12 (14)
C4—C3—H3A	120.0	C17—C16—C15	118.33 (15)
C5—C4—C3	119.99 (16)	C17—C16—C21	120.70 (13)
C5—C4—H4A	120.0	C15—C16—C21	120.97 (14)
C3—C4—H4A	120.0	C16—C17—C18	122.38 (14)
C6—C5—C4	120.41 (15)	C16—C17—H17A	118.8
C6—C5—H5A	119.8	C18—C17—H17A	118.8
C4—C5—H5A	119.8	O2—C18—C19	125.58 (15)
C5—C6—C7	120.02 (15)	O2—C18—C17	115.06 (13)
C5—C6—H6A	120.0	C19—C18—C17	119.35 (14)
C7—C6—H6A	120.0	C18—C19—C20	119.34 (15)
C6—C7—C2	120.30 (15)	C18—C19—H19A	120.3
C6—C7—H7A	119.9	C20—C19—H19A	120.3
C2—C7—H7A	119.9	C15—C20—C19	121.61 (14)
N1—C8—C9	114.91 (13)	C15—C20—H20A	119.2
N1—C8—C1	106.44 (13)	C19—C20—H20A	119.2
C9—C8—C1	106.20 (12)	C16—C21—H21A	109.5
N1—C8—H8A	109.7	C16—C21—H21B	109.5
C9—C8—H8A	109.7	H21A—C21—H21B	109.5
C1—C8—H8A	109.7	C16—C21—H21C	109.5
C10—C9—C14	118.68 (13)	H21A—C21—H21C	109.5
C10—C9—C8	121.58 (13)	H21B—C21—H21C	109.5
C14—C9—C8	119.71 (13)	O2—C22—H22A	109.5
C9—C10—C11	120.40 (15)	O2—C22—H22B	109.5
C9—C10—H10A	119.8	H22A—C22—H22B	109.5
C11—C10—H10A	119.8	O2—C22—H22C	109.5
C12—C11—C10	120.28 (15)	H22A—C22—H22C	109.5
C12—C11—H11A	119.9	H22B—C22—H22C	109.5
C10—C11—H11A	119.9	C15—N1—C8	124.59 (13)
C13—C12—C11	119.71 (14)	C15—N1—H1A	117.7
C13—C12—H12A	120.1	C8—N1—H1A	117.7
C11—C12—H12A	120.1	C18—O2—C22	117.49 (13)
C12—C13—C14	120.05 (15)

O1—C1—C2—C3	−160.36 (14)	C11—C12—C13—C14	0.1 (2)
C8—C1—C2—C3	22.1 (2)	C12—C13—C14—C9	−0.6 (2)
O1—C1—C2—C7	17.0 (2)	C10—C9—C14—C13	0.8 (2)
C8—C1—C2—C7	−160.60 (12)	C8—C9—C14—C13	−177.33 (12)
C7—C2—C3—C4	−1.2 (2)	C20—C15—C16—C17	0.0 (2)
C1—C2—C3—C4	176.15 (14)	N1—C15—C16—C17	178.73 (13)
C2—C3—C4—C5	0.9 (2)	C20—C15—C16—C21	179.37 (13)
C3—C4—C5—C6	0.3 (2)	N1—C15—C16—C21	−1.9 (2)
C4—C5—C6—C7	−1.3 (2)	C15—C16—C17—C18	0.4 (2)
C5—C6—C7—C2	1.0 (2)	C21—C16—C17—C18	−178.96 (14)
C3—C2—C7—C6	0.2 (2)	C16—C17—C18—O2	178.75 (13)
C1—C2—C7—C6	−177.25 (13)	C16—C17—C18—C19	−0.8 (2)
O1—C1—C8—N1	21.30 (18)	O2—C18—C19—C20	−178.70 (14)
C2—C1—C8—N1	−161.10 (12)	C17—C18—C19—C20	0.8 (2)
O1—C1—C8—C9	−101.58 (16)	N1—C15—C20—C19	−178.65 (14)
C2—C1—C8—C9	76.02 (16)	C16—C15—C20—C19	0.0 (2)
N1—C8—C9—C10	135.07 (14)	C18—C19—C20—C15	−0.4 (2)
C1—C8—C9—C10	−107.56 (15)	C20—C15—N1—C8	−14.1 (2)
N1—C8—C9—C14	−46.83 (17)	C16—C15—N1—C8	167.24 (13)
C1—C8—C9—C14	70.54 (15)	C9—C8—N1—C15	−57.18 (19)
C14—C9—C10—C11	−0.5 (2)	C1—C8—N1—C15	−174.41 (13)
C8—C9—C10—C11	177.64 (12)	C19—C18—O2—C22	1.2 (2)
C9—C10—C11—C12	−0.1 (2)	C17—C18—O2—C22	−178.33 (16)
C10—C11—C12—C13	0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	2.22	2.609 (3)	107
C11—H11A···O1ⁱ	0.95	2.48	3.352 (4)	153

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁NO₂
M_r	331.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.570 (12), 8.009 (8), 18.091 (17)
β (°)	100.544 (15)
V (Å³)	1791 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.21 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.984, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	28799, 4122, 2935
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.112, 1.05
No. of reflections	4122
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.25

Computer programs: SMART (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	2.22	2.609 (3)	107
C11—H11A···O1ⁱ	0.95	2.48	3.352 (4)	153

Symmetry code: (i) x, y+1, z.

Acknowledgements

This work was supported by the Mersin University Research Fund [Project No. BAP-SBE FK (SZ) 2008–8 YL].

References

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