N-(2,3-Dimethyl­phen­yl)-2,2,2-trimethyl­acetamide

Gowda, B.T.; Foro, S.; Terao, H.; Fuess, H.

doi:10.1107/S1600536809021229

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1529

doi:10.1107/S1600536809021229

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N-(2,3-Dimethylphenyl)-2,2,2-trimethylacetamide

B. Thimme Gowda,^a ^* Sabine Foro,^b Hiromitsu Terao ^c and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cFaculty of Integrated Arts and Sciences, Tokushima University, Minamijosanjima-cho, Tokushima 770-8502, Japan
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 16 May 2009; accepted 4 June 2009; online 10 June 2009)

The N—H bond in the title compound, C₁₃H₁₉NO, is anti to the C=O bond and is also anti to both the 2- and 3-methyl substituents in the aromatic ring. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains propagating along the c axis.

Related literature

For the preparation of the title compound, see: Shilpa & Gowda (2007 ). For related structures, see: Gowda et al. (2007a ,b ,c ).

Experimental

Crystal data

C₁₃H₁₉NO
M_r = 205.29
Monoclinic, P 2₁ /c
a = 18.276 (4) Å
b = 8.227 (2) Å
c = 8.633 (2) Å
β = 97.94 (2)°
V = 1285.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 299 K
0.45 × 0.16 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ) T_min = 0.971, T_max = 0.992
4295 measured reflections
2349 independent reflections
1214 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.221
S = 0.96
2349 reflections
195 parameters
112 restraints
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.94	2.11	2.966 (3)	151
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 $[Oxford Diffraction (2004). CrysAlis CCD. Oxford Diffraction Ltd, Köln, Germany.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis RED. Oxford Diffraction Ltd, Köln, Germany.]$ ); data reduction: CrysAlis RED; 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, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021229/ci2806sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021229/ci2806Isup2.hkl

checkCIF report

Comment top

As part of a study of the effect of ring and side chain substitutions on the crystal structures of chemically and biologically important class of compounds such as aromatic amides (Gowda et al., 2007a, b, c), the crystal structure of 2,2,2-trimethyl-N-(2,3-dimethylphenyl)-acetamide has been determined.

The conformation of the N–H bond in the title compound is anti to both the 2- and 3-methyl substituents in the aromatic ring (Fig. 1), in contrast to the syn conformation observed with respect to both the 2- and 3-chloro substituents in 2,2,2-trimethyl-N-(2,3-dichlorophenyl)acetamide (Gowda et al., 2007a), syn conformation with respect to the 2-methyl substituent in 2,2,2-trimethyl-N- (2-methylphenyl)acetamide (Gowda et al., 2007b) and anti conformation with respect to 3-methyl substituent in 2,2,2-trimethyl-N- (3-methylphenyl)acetamide (Gowda et al., 2007c). Furthermore, the conformation of the C═O bond is anti to the N—H bond in the amide segment.

In the title compound, the molecules are linked into chains (Fig. 2) running along the c axis by intermolecular N—H···O hydrogen bonds (Table 1).

Related literature top

For the preparation of the title compound, see: Shilpa & Gowda (2007). For related structures, see: Gowda et al. (2007a,b,c).

Experimental top

The title compound was prepared according to the literature method (Shilpa & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Shilpa & Gowda, 2007). Single crystals of the title compound were grown by slow evaporation of its ethanolic solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. All disorder components are shown.
	Fig. 2. Molecular packing of the title compound, viewed down the b axis. Only the major disorder component is shown. Hydrogen bonds are shown as dashed lines.

N-(2,3-Dimethylphenyl)-2,2,2-trimethylacetamide top

Crystal data top

C₁₃H₁₉NO	F(000) = 448
M_r = 205.29	D_x = 1.061 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1033 reflections
a = 18.276 (4) Å	θ = 2.7–27.9°
b = 8.227 (2) Å	µ = 0.07 mm⁻¹
c = 8.633 (2) Å	T = 299 K
β = 97.94 (2)°	Needle, colourless
V = 1285.6 (5) Å³	0.45 × 0.16 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2349 independent reflections
Radiation source: fine-focus sealed tube	1214 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Rotation method data acquisition using ω and ϕ scans	θ_max = 25.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −17→21
T_min = 0.971, T_max = 0.992	k = −6→9
4295 measured reflections	l = −10→8

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.221	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.1311P)²] where P = (F_o² + 2F_c²)/3
2349 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.28 e Å⁻³
112 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₃H₁₉NO	V = 1285.6 (5) Å³
M_r = 205.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.276 (4) Å	µ = 0.07 mm⁻¹
b = 8.227 (2) Å	T = 299 K
c = 8.633 (2) Å	0.45 × 0.16 × 0.08 mm
β = 97.94 (2)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2349 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	1214 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.992	R_int = 0.047
4295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	112 restraints
wR(F²) = 0.221	H-atom parameters constrained
S = 0.96	Δρ_max = 0.28 e Å⁻³
2349 reflections	Δρ_min = −0.24 e Å⁻³
195 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	Occ. (<1)
O1	0.19392 (11)	0.0929 (2)	0.5063 (2)	0.0698 (7)
N1	0.23113 (12)	0.2060 (3)	0.2915 (2)	0.0563 (7)
H1N	0.2239	0.2356	0.1850	0.068*
C1	0.28809 (14)	0.3034 (3)	0.3784 (3)	0.0502 (7)
C2	0.34834 (14)	0.2312 (3)	0.4711 (3)	0.0519 (7)
C3	0.40102 (15)	0.3326 (4)	0.5567 (3)	0.0618 (8)
C4	0.39304 (17)	0.4983 (4)	0.5429 (3)	0.0733 (9)
H4	0.4278	0.5652	0.6002	0.088*
C5	0.33513 (19)	0.5685 (4)	0.4467 (4)	0.0789 (10)
H5	0.3320	0.6809	0.4369	0.095*
C6	0.28169 (17)	0.4699 (3)	0.3649 (3)	0.0652 (8)
H6	0.2418	0.5157	0.3012	0.078*
C7	0.18685 (15)	0.1087 (3)	0.3635 (3)	0.0533 (7)
C8	0.12776 (15)	0.0097 (3)	0.2593 (3)	0.0636 (8)
C9	0.1112 (4)	0.0650 (10)	0.0899 (5)	0.086 (2)	0.743 (14)
H9A	0.0865	0.1682	0.0853	0.128*	0.743 (14)
H9B	0.0801	−0.0136	0.0309	0.128*	0.743 (14)
H9C	0.1566	0.0752	0.0465	0.128*	0.743 (14)
C10	0.0569 (3)	0.0106 (12)	0.3340 (8)	0.100 (3)	0.743 (14)
H10A	0.0391	0.1201	0.3385	0.150*	0.743 (14)
H10B	0.0667	−0.0329	0.4380	0.150*	0.743 (14)
H10C	0.0202	−0.0548	0.2727	0.150*	0.743 (14)
C11	0.1582 (4)	−0.1659 (6)	0.2620 (10)	0.101 (3)	0.743 (14)
H11A	0.2051	−0.1661	0.2242	0.151*	0.743 (14)
H11B	0.1242	−0.2338	0.1964	0.151*	0.743 (14)
H11C	0.1640	−0.2066	0.3672	0.151*	0.743 (14)
C9A	0.1107 (14)	−0.144 (2)	0.347 (3)	0.091 (7)	0.153 (7)
H9D	0.0780	−0.1177	0.4215	0.136*	0.153 (7)
H9E	0.1558	−0.1881	0.4012	0.136*	0.153 (7)
H9F	0.0877	−0.2228	0.2742	0.136*	0.153 (7)
C10A	0.1509 (13)	−0.029 (3)	0.0996 (17)	0.082 (7)	0.153 (7)
H10D	0.1342	0.0566	0.0273	0.122*	0.153 (7)
H10E	0.1293	−0.1299	0.0618	0.122*	0.153 (7)
H10F	0.2038	−0.0366	0.1096	0.122*	0.153 (7)
C11A	0.0616 (9)	0.129 (2)	0.242 (3)	0.082 (6)	0.153 (7)
H11D	0.0791	0.2375	0.2295	0.124*	0.153 (7)
H11E	0.0374	0.1235	0.3336	0.124*	0.153 (7)
H11F	0.0274	0.0996	0.1517	0.124*	0.153 (7)
C9B	0.072 (2)	−0.059 (7)	0.360 (6)	0.085 (11)	0.104 (13)
H9G	0.0440	0.0291	0.3957	0.128*	0.104 (13)
H9H	0.0978	−0.1152	0.4480	0.128*	0.104 (13)
H9I	0.0391	−0.1324	0.2983	0.128*	0.104 (13)
C11B	0.089 (3)	0.128 (6)	0.138 (7)	0.111 (19)	0.104 (13)
H11G	0.0842	0.2324	0.1855	0.167*	0.104 (13)
H11H	0.0406	0.0873	0.0987	0.167*	0.104 (13)
H11I	0.1173	0.1392	0.0528	0.167*	0.104 (13)
C10B	0.173 (2)	−0.115 (6)	0.180 (7)	0.095 (11)	0.104 (13)
H10G	0.1773	−0.0790	0.0753	0.142*	0.104 (13)
H10H	0.1490	−0.2185	0.1756	0.142*	0.104 (13)
H10I	0.2216	−0.1242	0.2383	0.142*	0.104 (13)
C12	0.35791 (18)	0.0495 (4)	0.4751 (4)	0.0746 (9)
H12A	0.3305	0.0027	0.3830	0.112*
H12B	0.3401	0.0065	0.5662	0.112*
H12C	0.4093	0.0234	0.4785	0.112*
C13	0.46617 (16)	0.2627 (5)	0.6612 (4)	0.0859 (11)
H13A	0.4976	0.2062	0.5987	0.129*
H13B	0.4490	0.1883	0.7340	0.129*
H13C	0.4935	0.3490	0.7175	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0848 (15)	0.0745 (15)	0.0504 (12)	−0.0125 (11)	0.0108 (9)	0.0006 (10)
N1	0.0721 (15)	0.0500 (14)	0.0461 (12)	−0.0083 (12)	0.0054 (10)	0.0016 (10)
C1	0.0617 (17)	0.0420 (16)	0.0468 (13)	−0.0051 (12)	0.0073 (12)	−0.0018 (12)
C2	0.0576 (16)	0.0471 (17)	0.0527 (14)	0.0025 (13)	0.0132 (12)	0.0018 (12)
C3	0.0570 (17)	0.071 (2)	0.0577 (16)	−0.0049 (15)	0.0082 (13)	0.0023 (15)
C4	0.074 (2)	0.069 (2)	0.073 (2)	−0.0191 (17)	−0.0008 (16)	−0.0073 (16)
C5	0.104 (3)	0.0400 (18)	0.089 (2)	−0.0114 (17)	0.001 (2)	−0.0069 (16)
C6	0.076 (2)	0.0459 (18)	0.0706 (18)	0.0028 (15)	−0.0011 (15)	0.0033 (14)
C7	0.0631 (17)	0.0461 (17)	0.0515 (16)	0.0017 (13)	0.0104 (12)	0.0003 (12)
C8	0.0728 (19)	0.0537 (18)	0.0629 (18)	−0.0116 (14)	0.0046 (14)	−0.0043 (14)
C9	0.085 (4)	0.100 (5)	0.064 (3)	−0.027 (3)	−0.013 (3)	−0.001 (3)
C10	0.081 (3)	0.122 (6)	0.098 (4)	−0.030 (4)	0.016 (3)	−0.010 (4)
C11	0.135 (5)	0.051 (3)	0.111 (5)	−0.012 (3)	−0.004 (4)	−0.017 (3)
C9A	0.095 (11)	0.080 (9)	0.101 (10)	−0.016 (8)	0.024 (8)	0.008 (8)
C10A	0.085 (10)	0.085 (11)	0.073 (8)	−0.005 (8)	0.006 (7)	−0.008 (8)
C11A	0.076 (9)	0.085 (9)	0.083 (10)	−0.004 (7)	0.000 (7)	−0.011 (8)
C9B	0.084 (13)	0.082 (15)	0.092 (13)	−0.006 (9)	0.018 (9)	0.011 (9)
C11B	0.11 (2)	0.12 (2)	0.11 (2)	−0.002 (10)	0.008 (10)	−0.005 (10)
C10B	0.103 (13)	0.092 (14)	0.092 (14)	−0.008 (9)	0.020 (9)	−0.013 (10)
C12	0.082 (2)	0.061 (2)	0.082 (2)	0.0128 (16)	0.0142 (17)	0.0059 (16)
C13	0.065 (2)	0.110 (3)	0.081 (2)	−0.001 (2)	0.0016 (16)	0.006 (2)

Geometric parameters (Å, º) top

O1—C7	1.229 (3)	C10—H10B	0.96
N1—C7	1.350 (3)	C10—H10C	0.96
N1—C1	1.440 (3)	C11—H11A	0.96
N1—H1N	0.94	C11—H11B	0.96
C1—C6	1.378 (4)	C11—H11C	0.96
C1—C2	1.401 (3)	C9A—H9D	0.96
C2—C3	1.405 (4)	C9A—H9E	0.96
C2—C12	1.505 (4)	C9A—H9F	0.96
C3—C4	1.374 (4)	C10A—H10D	0.96
C3—C13	1.505 (4)	C10A—H10E	0.96
C4—C5	1.378 (4)	C10A—H10F	0.96
C4—H4	0.93	C11A—H11D	0.96
C5—C6	1.386 (4)	C11A—H11E	0.96
C5—H5	0.93	C11A—H11F	0.96
C6—H6	0.93	C9B—H9G	0.96
C7—C8	1.539 (4)	C9B—H9H	0.96
C8—C9	1.522 (4)	C9B—H9I	0.96
C8—C10	1.525 (5)	C11B—H11G	0.96
C8—C9A	1.529 (8)	C11B—H11H	0.96
C8—C10A	1.530 (8)	C11B—H11I	0.96
C8—C9B	1.533 (8)	C10B—H10G	0.96
C8—C11B	1.534 (8)	C10B—H10H	0.96
C8—C10B	1.539 (8)	C10B—H10I	0.96
C8—C11	1.547 (5)	C12—H12A	0.96
C8—C11A	1.547 (8)	C12—H12B	0.96
C9—H9A	0.96	C12—H12C	0.96
C9—H9B	0.96	C13—H13A	0.96
C9—H9C	0.96	C13—H13B	0.96
C10—H10A	0.96	C13—H13C	0.96

C7—N1—C1	121.8 (2)	C8—C11—H11B	109.5
C7—N1—H1N	126.2	H11A—C11—H11B	109.5
C1—N1—H1N	111.0	C8—C11—H11C	109.5
C6—C1—C2	121.4 (2)	H11A—C11—H11C	109.5
C6—C1—N1	117.5 (2)	H11B—C11—H11C	109.5
C2—C1—N1	121.1 (2)	C8—C9A—H9D	109.5
C1—C2—C3	118.4 (2)	C8—C9A—H9E	109.5
C1—C2—C12	120.9 (2)	H9D—C9A—H9E	109.5
C3—C2—C12	120.6 (3)	C8—C9A—H9F	109.5
C4—C3—C2	119.1 (3)	H9D—C9A—H9F	109.5
C4—C3—C13	119.8 (3)	H9E—C9A—H9F	109.5
C2—C3—C13	121.1 (3)	C8—C10A—H10D	109.5
C3—C4—C5	122.1 (3)	C8—C10A—H10E	109.5
C3—C4—H4	119.0	H10D—C10A—H10E	109.5
C5—C4—H4	119.0	C8—C10A—H10F	109.5
C4—C5—C6	119.4 (3)	H10D—C10A—H10F	109.5
C4—C5—H5	120.3	H10E—C10A—H10F	109.5
C6—C5—H5	120.3	C8—C11A—H11D	109.5
C1—C6—C5	119.5 (3)	C8—C11A—H11E	109.5
C1—C6—H6	120.2	H11D—C11A—H11E	109.5
C5—C6—H6	120.2	C8—C11A—H11F	109.5
O1—C7—N1	122.6 (2)	H11D—C11A—H11F	109.5
O1—C7—C8	119.9 (2)	H11E—C11A—H11F	109.5
N1—C7—C8	117.5 (2)	C8—C9B—H9G	109.5
C9—C8—C10	109.7 (3)	C8—C9B—H9H	109.5
C9A—C8—C10A	112.2 (7)	H9G—C9B—H9H	109.5
C9B—C8—C11B	110 (3)	C8—C9B—H9I	109.5
C9B—C8—C10B	117 (3)	H9G—C9B—H9I	109.5
C11B—C8—C10B	110 (3)	H9H—C9B—H9I	109.5
C9—C8—C7	115.7 (3)	C8—C11B—H11G	109.5
C10—C8—C7	108.6 (3)	C8—C11B—H11H	109.5
C9A—C8—C7	108.8 (10)	H11G—C11B—H11H	109.5
C10A—C8—C7	112.1 (9)	C8—C11B—H11I	109.5
C9B—C8—C7	109 (2)	H11G—C11B—H11I	109.5
C11B—C8—C7	107 (2)	H11H—C11B—H11I	109.5
C10B—C8—C7	103.6 (16)	C8—C10B—H10G	109.5
C9—C8—C11	108.5 (3)	C8—C10B—H10H	109.5
C10—C8—C11	108.8 (3)	H10G—C10B—H10H	109.5
C7—C8—C11	105.3 (3)	C8—C10B—H10I	109.5
C9A—C8—C11A	111.3 (7)	H10G—C10B—H10I	109.5
C10A—C8—C11A	110.6 (7)	H10H—C10B—H10I	109.5
C8—C9—H9A	109.5	C2—C12—H12A	109.5
C8—C9—H9B	109.5	C2—C12—H12B	109.5
H9A—C9—H9B	109.5	H12A—C12—H12B	109.5
C8—C9—H9C	109.5	C2—C12—H12C	109.5
H9A—C9—H9C	109.5	H12A—C12—H12C	109.5
H9B—C9—H9C	109.5	H12B—C12—H12C	109.5
C8—C10—H10A	109.5	C3—C13—H13A	109.5
C8—C10—H10B	109.5	C3—C13—H13B	109.5
H10A—C10—H10B	109.5	H13A—C13—H13B	109.5
C8—C10—H10C	109.5	C3—C13—H13C	109.5
H10A—C10—H10C	109.5	H13A—C13—H13C	109.5
H10B—C10—H10C	109.5	H13B—C13—H13C	109.5
C8—C11—H11A	109.5

C7—N1—C1—C6	−116.5 (3)	O1—C7—C8—C9	166.5 (5)
C7—N1—C1—C2	64.6 (3)	N1—C7—C8—C9	−16.0 (5)
C6—C1—C2—C3	2.9 (4)	O1—C7—C8—C10	42.6 (5)
N1—C1—C2—C3	−178.2 (2)	N1—C7—C8—C10	−139.9 (5)
C6—C1—C2—C12	−175.1 (2)	O1—C7—C8—C9A	−24.7 (11)
N1—C1—C2—C12	3.8 (4)	N1—C7—C8—C9A	152.8 (11)
C1—C2—C3—C4	−2.1 (4)	O1—C7—C8—C10A	−149.4 (11)
C12—C2—C3—C4	176.0 (3)	N1—C7—C8—C10A	28.1 (11)
C1—C2—C3—C13	178.7 (2)	O1—C7—C8—C9B	16 (2)
C12—C2—C3—C13	−3.3 (4)	N1—C7—C8—C9B	−166 (2)
C2—C3—C4—C5	−0.4 (5)	O1—C7—C8—C11B	135 (3)
C13—C3—C4—C5	178.9 (3)	N1—C7—C8—C11B	−48 (3)
C3—C4—C5—C6	2.1 (5)	O1—C7—C8—C10B	−109 (3)
C2—C1—C6—C5	−1.2 (4)	N1—C7—C8—C10B	69 (3)
N1—C1—C6—C5	179.8 (3)	O1—C7—C8—C11	−73.8 (5)
C4—C5—C6—C1	−1.3 (5)	N1—C7—C8—C11	103.7 (5)
C1—N1—C7—O1	−2.5 (4)	O1—C7—C8—C11A	92.6 (11)
C1—N1—C7—C8	−180.0 (2)	N1—C7—C8—C11A	−89.9 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.94	2.11	2.966 (3)	151

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₉NO
M_r	205.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	18.276 (4), 8.227 (2), 8.633 (2)
β (°)	97.94 (2)
V (Å³)	1285.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.45 × 0.16 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.971, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	4295, 2349, 1214
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.221, 0.96
No. of reflections	2349
No. of parameters	195
No. of restraints	112
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.94	2.11	2.966 (3)	151

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for resumption of his research fellowship.

References

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