N-(3,4-Dimethyl­phen­yl)acetamide

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

doi:10.1107/S1600536807060916

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o11

https://doi.org/10.1107/S1600536807060916

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N-(3,4-Dimethylphenyl)acetamide

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

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 17 November 2007; accepted 19 November 2007; online 6 December 2007)

The conformation of the N—H bond in the title compound (34DMPA), C₁₀H₁₃NO, is syn to the 3-methyl substituent in the aromatic ring, in contrast to the anti conformation observed with respect to the 3-chloro substituent in N-(3,4-dichlorophenyl)acetamide (34DCPA). The asymmetric unit of the structure contains three molecules. The bond parameters in 34DMPA are similar to those in 34DCPA, N-(2,6-dimethylphenyl)acetamide, N-(3,5-dimethylphenyl)acetamide and other acetanilides. The molecules in 34DMPA are linked into infinite chains through N—H⋯O hydrogen bonding.

Related literature

For related literature, see: Gowda et al. (2007a ,b ); Gowda, Kozisek, Svoboda & Fuess (2007 ); Gowda, Kožíšek, Tokarčík & Fuess (2007 ); Jones et al. (1990 ); Shilpa & Gowda (2007 ).

Experimental

Crystal data

C₁₀H₁₃NO
M_r = 163.21
Triclinic, $[P \overline 1]$
a = 6.749 (1) Å
b = 14.281 (2) Å
c = 15.005 (2) Å
α = 85.33 (1)°
β = 79.81 (1)°
γ = 87.58 (1)°
V = 1418.1 (3) Å³
Z = 6
Cu Kα radiation
μ = 0.59 mm⁻¹
T = 299 (2) K
0.35 × 0.33 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
5528 measured reflections
5025 independent reflections
3386 reflections with I > 2σ(I)
R_int = 0.044
3 standard reflections frequency: 120 min intensity decay: 2.0%

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.210
S = 1.03
5025 reflections
344 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O3	0.88 (3)	2.08 (3)	2.956 (3)	177 (3)
N3—H3N⋯O2	0.86 (3)	2.14 (3)	2.989 (3)	172 (3)
N2—H2N⋯O1ⁱ	0.98 (3)	1.92 (3)	2.893 (3)	170 (2)
Symmetry code: (i) x, y+1, z.

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996 ); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807060916/lw2051sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807060916/lw2051Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of N-(3,4-dimethylphenyl)-acetamide (34DMPA) has been determined to study the effect of substituents on the structures of N-aromatic amides (Gowda et al., 2007a, b; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007). The conformation of the N—H bond in 34DMPA is syn to the 3-methyl substituent in the aromatic ring, in contrast to the anti conformation obseved with respect to the 3-chloro substituent in N-(3,4-dichlorophenyl)-acetamide (34DCPA) (Jones et al., 1990). The asymmetric unit of the structure contains 3 molecules. The bond parameters in 34DMPA are similar to those in 34DCPA (Jones et al., 1990), N-(2,6-dimethylphenyl)-acetamide (Gowda et al., 2007b), N-(3,5-dimethylphenyl)-acetamide (Gowda, Kožíšek, Tokarčík & Fuess, 2007) and other acetanilides. The molecules in 34DMPA are linked into chains through N—H···O hydrogen bonding (Table 1 & Fig. 2).

Related literature top

For related literature, see: Gowda et al. (2007a,b); Kozisek, Svoboda & Fuess (2007); Gowda, Kožíšek, Tokarčík & Fuess (2007); Jones et al. (1990); Shilpa & Gowda (2007).

Experimental top

The title compound was prepared according to the literature method (Shilpa and 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 and Gowda, 2007). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Structure description top

For related literature, see: Gowda et al. (2007a,b); Kozisek, Svoboda & Fuess (2007); Gowda, Kožíšek, Tokarčík & Fuess (2007); Jones et al. (1990); Shilpa & Gowda (2007).

Computing details top

Data collection: CAD-4-PC Version (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Version (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.

N-(3,4-Dimethylphenyl)acetamide top

Crystal data top

C₁₀H₁₃NO	Z = 6
M_r = 163.21	F(000) = 528
Triclinic, P1	D_x = 1.147 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54180 Å
a = 6.749 (1) Å	Cell parameters from 25 reflections
b = 14.281 (2) Å	θ = 3.1–22.1°
c = 15.005 (2) Å	µ = 0.59 mm⁻¹
α = 85.33 (1)°	T = 299 K
β = 79.81 (1)°	Prism, colourless
γ = 87.58 (1)°	0.35 × 0.33 × 0.18 mm
V = 1418.1 (3) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.044
Radiation source: fine-focus sealed tube	θ_max = 66.9°, θ_min = 3.0°
Graphite monochromator	h = −8→1
ω/2θ scans	k = −17→17
5528 measured reflections	l = −17→17
5025 independent reflections	3 standard reflections every 120 min
3386 reflections with I > 2σ(I)	intensity decay: 2.0%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.210	w = 1/[σ²(F_o²) + (0.1316P)² + 0.1229P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
5025 reflections	Δρ_max = 0.26 e Å⁻³
344 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (7)

Crystal data top

C₁₀H₁₃NO	γ = 87.58 (1)°
M_r = 163.21	V = 1418.1 (3) Å³
Triclinic, P1	Z = 6
a = 6.749 (1) Å	Cu Kα radiation
b = 14.281 (2) Å	µ = 0.59 mm⁻¹
c = 15.005 (2) Å	T = 299 K
α = 85.33 (1)°	0.35 × 0.33 × 0.18 mm
β = 79.81 (1)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.044
5528 measured reflections	3 standard reflections every 120 min
5025 independent reflections	intensity decay: 2.0%
3386 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.210	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.26 e Å⁻³
5025 reflections	Δρ_min = −0.27 e Å⁻³
344 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
O1	0.6611 (4)	0.21887 (13)	0.27754 (16)	0.0935 (7)
N1	0.7204 (3)	0.37376 (14)	0.26524 (16)	0.0647 (6)
H1N	0.702 (4)	0.428 (2)	0.2362 (19)	0.078*
C1	0.8633 (4)	0.37519 (17)	0.32314 (17)	0.0633 (6)
C2	1.0021 (4)	0.44579 (19)	0.3073 (2)	0.0713 (7)
H2	1.0045	0.4879	0.2565	0.086*
C3	1.1384 (4)	0.4555 (2)	0.3653 (2)	0.0794 (8)
C4	1.1409 (5)	0.3917 (3)	0.4390 (2)	0.0906 (10)
C5	1.0037 (6)	0.3211 (3)	0.4542 (2)	0.0970 (10)
H5	1.0053	0.2774	0.5036	0.116*
C6	0.8637 (5)	0.3128 (2)	0.3985 (2)	0.0849 (9)
H6	0.7702	0.2654	0.4117	0.102*
C7	0.6247 (4)	0.29887 (17)	0.24731 (19)	0.0658 (6)
C8	0.4682 (4)	0.31912 (19)	0.1893 (2)	0.0778 (8)
H8A	0.4651	0.3850	0.1708	0.093*
H8B	0.3390	0.3016	0.2232	0.093*
H8C	0.4995	0.2838	0.1367	0.093*
C9	1.2754 (5)	0.5374 (3)	0.3480 (3)	0.1155 (13)
H9A	1.2499	0.5751	0.2951	0.139*
H9B	1.4130	0.5149	0.3385	0.139*
H9C	1.2511	0.5747	0.3995	0.139*
C10	1.2889 (7)	0.3980 (4)	0.5030 (3)	0.1352 (18)
H10A	1.4232	0.4007	0.4689	0.162*
H10B	1.2785	0.3437	0.5456	0.162*
H10C	1.2588	0.4537	0.5353	0.162*
O2	0.6415 (3)	0.89842 (12)	0.17410 (15)	0.0810 (6)
N2	0.7398 (3)	1.02533 (14)	0.23505 (15)	0.0625 (5)
H2N	0.709 (4)	1.092 (2)	0.2425 (18)	0.075*
C11	0.9017 (4)	0.98806 (17)	0.27568 (18)	0.0613 (6)
C12	0.9873 (4)	1.04469 (19)	0.32918 (18)	0.0697 (7)
H12	0.9362	1.1057	0.3360	0.084*
C13	1.1444 (5)	1.0139 (2)	0.37231 (19)	0.0775 (8)
C14	1.2212 (4)	0.9219 (2)	0.3629 (2)	0.0810 (8)
C15	1.1404 (5)	0.8675 (2)	0.3084 (3)	0.0908 (10)
H15	1.1927	0.8068	0.3009	0.109*
C16	0.9848 (4)	0.89835 (19)	0.2641 (2)	0.0822 (9)
H16	0.9360	0.8594	0.2267	0.099*
C17	0.6230 (4)	0.98221 (17)	0.18788 (17)	0.0617 (6)
C18	0.4661 (4)	1.04309 (19)	0.1511 (2)	0.0746 (7)
H18A	0.4555	1.1026	0.1774	0.089*
H18B	0.3387	1.0130	0.1660	0.089*
H18C	0.5031	1.0529	0.0863	0.089*
C19	1.2353 (6)	1.0776 (3)	0.4266 (3)	0.1110 (12)
H19A	1.1668	1.1379	0.4254	0.133*
H19B	1.3752	1.0848	0.4013	0.133*
H19C	1.2225	1.0513	0.4882	0.133*
C20	1.3884 (5)	0.8838 (3)	0.4104 (3)	0.1128 (13)
H20A	1.5045	0.9218	0.3914	0.135*
H20B	1.4218	0.8203	0.3953	0.135*
H20C	1.3459	0.8849	0.4748	0.135*
O3	0.6498 (3)	0.55410 (11)	0.16267 (14)	0.0773 (6)
N3	0.5363 (3)	0.70443 (13)	0.14131 (14)	0.0607 (5)
H3N	0.555 (4)	0.760 (2)	0.1545 (18)	0.073*
C21	0.3877 (4)	0.69495 (15)	0.08863 (16)	0.0565 (6)
C22	0.2832 (4)	0.77608 (17)	0.06384 (16)	0.0609 (6)
H22	0.3169	0.8330	0.0823	0.073*
C23	0.1323 (4)	0.7758 (2)	0.01327 (18)	0.0683 (7)
C24	0.0808 (4)	0.6904 (2)	−0.0150 (2)	0.0764 (8)
C25	0.1861 (5)	0.6102 (2)	0.0097 (2)	0.0824 (8)
H25	0.1532	0.5533	−0.0092	0.099*
C26	0.3366 (4)	0.60984 (18)	0.0604 (2)	0.0723 (7)
H26	0.4032	0.5540	0.0756	0.087*
C27	0.6556 (4)	0.63784 (16)	0.17531 (16)	0.0600 (6)
C28	0.7946 (5)	0.67177 (19)	0.2314 (2)	0.0846 (9)
H28A	0.9251	0.6808	0.1947	0.101*
H28B	0.8056	0.6261	0.2810	0.101*
H28C	0.7430	0.7303	0.2546	0.101*
C29	0.0253 (5)	0.8664 (3)	−0.0104 (2)	0.0974 (10)
H29A	−0.1148	0.8630	0.0161	0.117*
H29B	0.0386	0.8766	−0.0752	0.117*
H29C	0.0836	0.9175	0.0127	0.117*
C30	−0.0827 (5)	0.6855 (3)	−0.0706 (2)	0.1065 (12)
H30A	−0.2087	0.7060	−0.0365	0.128*
H30B	−0.0925	0.6218	−0.0854	0.128*
H30C	−0.0511	0.7254	−0.1256	0.128*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1197 (17)	0.0455 (10)	0.1293 (18)	0.0036 (10)	−0.0624 (14)	−0.0039 (10)
N1	0.0750 (14)	0.0435 (10)	0.0809 (14)	0.0084 (9)	−0.0294 (11)	−0.0085 (9)
C1	0.0722 (16)	0.0520 (13)	0.0701 (15)	0.0128 (11)	−0.0214 (13)	−0.0183 (11)
C2	0.0703 (16)	0.0615 (15)	0.0851 (18)	0.0085 (12)	−0.0187 (14)	−0.0180 (13)
C3	0.0669 (17)	0.0801 (19)	0.095 (2)	0.0081 (14)	−0.0113 (15)	−0.0384 (16)
C4	0.094 (2)	0.107 (3)	0.078 (2)	0.0302 (19)	−0.0285 (17)	−0.0381 (19)
C5	0.128 (3)	0.095 (2)	0.0727 (19)	0.019 (2)	−0.033 (2)	−0.0118 (17)
C6	0.112 (2)	0.0733 (18)	0.0740 (17)	0.0072 (16)	−0.0310 (17)	−0.0088 (14)
C7	0.0712 (15)	0.0480 (13)	0.0822 (17)	0.0085 (11)	−0.0229 (13)	−0.0134 (11)
C8	0.0755 (17)	0.0617 (15)	0.104 (2)	0.0046 (13)	−0.0362 (16)	−0.0142 (14)
C9	0.092 (2)	0.126 (3)	0.133 (3)	−0.020 (2)	−0.015 (2)	−0.041 (3)
C10	0.125 (3)	0.190 (5)	0.109 (3)	0.038 (3)	−0.060 (3)	−0.061 (3)
O2	0.0835 (13)	0.0536 (10)	0.1117 (15)	−0.0016 (9)	−0.0232 (11)	−0.0266 (10)
N2	0.0678 (12)	0.0451 (10)	0.0776 (13)	−0.0025 (9)	−0.0202 (11)	−0.0051 (9)
C11	0.0581 (13)	0.0532 (13)	0.0713 (15)	−0.0023 (10)	−0.0100 (12)	0.0011 (11)
C12	0.0714 (16)	0.0664 (16)	0.0741 (16)	0.0001 (12)	−0.0187 (14)	−0.0102 (12)
C13	0.0732 (17)	0.094 (2)	0.0659 (16)	−0.0067 (15)	−0.0133 (14)	−0.0036 (14)
C14	0.0640 (16)	0.089 (2)	0.0840 (19)	0.0010 (15)	−0.0099 (15)	0.0200 (16)
C15	0.0762 (19)	0.0631 (17)	0.132 (3)	0.0055 (14)	−0.0238 (19)	0.0067 (18)
C16	0.0772 (18)	0.0521 (14)	0.122 (2)	0.0023 (12)	−0.0285 (18)	−0.0108 (15)
C17	0.0597 (14)	0.0531 (13)	0.0713 (15)	−0.0071 (10)	−0.0063 (12)	−0.0077 (11)
C18	0.0770 (17)	0.0628 (15)	0.0889 (19)	−0.0060 (13)	−0.0286 (15)	−0.0025 (13)
C19	0.108 (3)	0.130 (3)	0.107 (3)	0.004 (2)	−0.044 (2)	−0.030 (2)
C20	0.088 (2)	0.131 (3)	0.116 (3)	0.004 (2)	−0.029 (2)	0.033 (2)
O3	0.0991 (14)	0.0402 (9)	0.1004 (14)	0.0032 (8)	−0.0406 (11)	−0.0032 (8)
N3	0.0747 (13)	0.0378 (10)	0.0753 (13)	0.0002 (9)	−0.0272 (11)	−0.0072 (9)
C21	0.0622 (14)	0.0466 (12)	0.0624 (13)	0.0019 (10)	−0.0150 (11)	−0.0074 (10)
C22	0.0681 (15)	0.0503 (12)	0.0650 (14)	0.0039 (10)	−0.0144 (12)	−0.0051 (10)
C23	0.0603 (14)	0.0786 (17)	0.0635 (15)	0.0098 (12)	−0.0093 (12)	−0.0006 (12)
C24	0.0604 (15)	0.098 (2)	0.0734 (17)	0.0008 (14)	−0.0160 (13)	−0.0144 (15)
C25	0.085 (2)	0.0730 (18)	0.098 (2)	−0.0096 (15)	−0.0327 (17)	−0.0188 (15)
C26	0.0814 (18)	0.0517 (14)	0.0914 (19)	−0.0013 (12)	−0.0318 (15)	−0.0141 (12)
C27	0.0740 (15)	0.0439 (12)	0.0643 (14)	−0.0023 (10)	−0.0202 (12)	0.0016 (10)
C28	0.111 (2)	0.0558 (15)	0.099 (2)	0.0038 (14)	−0.0545 (19)	−0.0015 (14)
C29	0.085 (2)	0.104 (2)	0.100 (2)	0.0300 (18)	−0.0245 (18)	0.0084 (19)
C30	0.076 (2)	0.159 (4)	0.093 (2)	0.002 (2)	−0.0321 (18)	−0.026 (2)

Geometric parameters (Å, º) top

O1—C7	1.226 (3)	C15—H15	0.9300
N1—C7	1.342 (3)	C16—H16	0.9300
N1—C1	1.410 (3)	C17—C18	1.494 (4)
N1—H1N	0.88 (3)	C18—H18A	0.9600
C1—C6	1.382 (4)	C18—H18B	0.9600
C1—C2	1.383 (4)	C18—H18C	0.9600
C2—C3	1.391 (4)	C19—H19A	0.9600
C2—H2	0.9300	C19—H19B	0.9600
C3—C4	1.376 (5)	C19—H19C	0.9600
C3—C9	1.500 (5)	C20—H20A	0.9600
C4—C5	1.376 (5)	C20—H20B	0.9600
C4—C10	1.514 (4)	C20—H20C	0.9600
C5—C6	1.382 (4)	O3—C27	1.229 (3)
C5—H5	0.9300	N3—C27	1.347 (3)
C6—H6	0.9300	N3—C21	1.399 (3)
C7—C8	1.488 (4)	N3—H3N	0.86 (3)
C8—H8A	0.9600	C21—C22	1.390 (3)
C8—H8B	0.9600	C21—C26	1.395 (3)
C8—H8C	0.9600	C22—C23	1.374 (4)
C9—H9A	0.9600	C22—H22	0.9300
C9—H9B	0.9600	C23—C24	1.400 (4)
C9—H9C	0.9600	C23—C29	1.503 (4)
C10—H10A	0.9600	C24—C25	1.382 (4)
C10—H10B	0.9600	C24—C30	1.504 (4)
C10—H10C	0.9600	C25—C26	1.372 (4)
O2—C17	1.228 (3)	C25—H25	0.9300
N2—C17	1.346 (3)	C26—H26	0.9300
N2—C11	1.408 (3)	C27—C28	1.486 (4)
N2—H2N	0.98 (3)	C28—H28A	0.9600
C11—C16	1.388 (4)	C28—H28B	0.9600
C11—C12	1.393 (4)	C28—H28C	0.9600
C12—C13	1.376 (4)	C29—H29A	0.9600
C12—H12	0.9300	C29—H29B	0.9600
C13—C14	1.401 (5)	C29—H29C	0.9600
C13—C19	1.487 (4)	C30—H30A	0.9600
C14—C15	1.366 (5)	C30—H30B	0.9600
C14—C20	1.499 (4)	C30—H30C	0.9600
C15—C16	1.378 (4)

C7—N1—C1	127.2 (2)	O2—C17—N2	123.6 (2)
C7—N1—H1N	119.3 (19)	O2—C17—C18	120.6 (2)
C1—N1—H1N	113.3 (19)	N2—C17—C18	115.8 (2)
C6—C1—C2	118.2 (3)	C17—C18—H18A	109.5
C6—C1—N1	123.0 (3)	C17—C18—H18B	109.5
C2—C1—N1	118.6 (2)	H18A—C18—H18B	109.5
C1—C2—C3	121.8 (3)	C17—C18—H18C	109.5
C1—C2—H2	119.1	H18A—C18—H18C	109.5
C3—C2—H2	119.1	H18B—C18—H18C	109.5
C4—C3—C2	119.6 (3)	C13—C19—H19A	109.5
C4—C3—C9	121.2 (3)	C13—C19—H19B	109.5
C2—C3—C9	119.2 (3)	H19A—C19—H19B	109.5
C5—C4—C3	118.5 (3)	C13—C19—H19C	109.5
C5—C4—C10	119.9 (4)	H19A—C19—H19C	109.5
C3—C4—C10	121.7 (4)	H19B—C19—H19C	109.5
C4—C5—C6	122.2 (3)	C14—C20—H20A	109.5
C4—C5—H5	118.9	C14—C20—H20B	109.5
C6—C5—H5	118.9	H20A—C20—H20B	109.5
C1—C6—C5	119.7 (3)	C14—C20—H20C	109.5
C1—C6—H6	120.2	H20A—C20—H20C	109.5
C5—C6—H6	120.2	H20B—C20—H20C	109.5
O1—C7—N1	122.5 (2)	C27—N3—C21	129.3 (2)
O1—C7—C8	121.8 (2)	C27—N3—H3N	114.5 (19)
N1—C7—C8	115.7 (2)	C21—N3—H3N	116.2 (18)
C7—C8—H8A	109.5	C22—C21—C26	118.2 (2)
C7—C8—H8B	109.5	C22—C21—N3	117.3 (2)
H8A—C8—H8B	109.5	C26—C21—N3	124.5 (2)
C7—C8—H8C	109.5	C23—C22—C21	122.9 (2)
H8A—C8—H8C	109.5	C23—C22—H22	118.6
H8B—C8—H8C	109.5	C21—C22—H22	118.6
C3—C9—H9A	109.5	C22—C23—C24	119.0 (2)
C3—C9—H9B	109.5	C22—C23—C29	119.8 (3)
H9A—C9—H9B	109.5	C24—C23—C29	121.2 (3)
C3—C9—H9C	109.5	C25—C24—C23	117.7 (3)
H9A—C9—H9C	109.5	C25—C24—C30	120.7 (3)
H9B—C9—H9C	109.5	C23—C24—C30	121.5 (3)
C4—C10—H10A	109.5	C26—C25—C24	123.7 (3)
C4—C10—H10B	109.5	C26—C25—H25	118.2
H10A—C10—H10B	109.5	C24—C25—H25	118.2
C4—C10—H10C	109.5	C25—C26—C21	118.6 (3)
H10A—C10—H10C	109.5	C25—C26—H26	120.7
H10B—C10—H10C	109.5	C21—C26—H26	120.7
C17—N2—C11	129.2 (2)	O3—C27—N3	123.1 (2)
C17—N2—H2N	116.1 (16)	O3—C27—C28	121.4 (2)
C11—N2—H2N	114.7 (16)	N3—C27—C28	115.5 (2)
C16—C11—C12	117.6 (3)	C27—C28—H28A	109.5
C16—C11—N2	123.8 (2)	C27—C28—H28B	109.5
C12—C11—N2	118.5 (2)	H28A—C28—H28B	109.5
C13—C12—C11	122.6 (3)	C27—C28—H28C	109.5
C13—C12—H12	118.7	H28A—C28—H28C	109.5
C11—C12—H12	118.7	H28B—C28—H28C	109.5
C12—C13—C14	119.0 (3)	C23—C29—H29A	109.5
C12—C13—C19	120.8 (3)	C23—C29—H29B	109.5
C14—C13—C19	120.1 (3)	H29A—C29—H29B	109.5
C15—C14—C13	118.1 (3)	C23—C29—H29C	109.5
C15—C14—C20	120.5 (3)	H29A—C29—H29C	109.5
C13—C14—C20	121.3 (3)	H29B—C29—H29C	109.5
C14—C15—C16	123.1 (3)	C24—C30—H30A	109.5
C14—C15—H15	118.5	C24—C30—H30B	109.5
C16—C15—H15	118.5	H30A—C30—H30B	109.5
C15—C16—C11	119.5 (3)	C24—C30—H30C	109.5
C15—C16—H16	120.3	H30A—C30—H30C	109.5
C11—C16—H16	120.3	H30B—C30—H30C	109.5

C7—N1—C1—C6	−29.7 (4)	C19—C13—C14—C20	3.1 (5)
C7—N1—C1—C2	154.5 (3)	C13—C14—C15—C16	−1.3 (5)
C6—C1—C2—C3	−0.6 (4)	C20—C14—C15—C16	179.1 (3)
N1—C1—C2—C3	175.4 (2)	C14—C15—C16—C11	−1.2 (5)
C1—C2—C3—C4	2.2 (4)	C12—C11—C16—C15	2.9 (4)
C1—C2—C3—C9	−175.8 (3)	N2—C11—C16—C15	−178.6 (3)
C2—C3—C4—C5	−1.6 (4)	C11—N2—C17—O2	1.1 (4)
C9—C3—C4—C5	176.3 (3)	C11—N2—C17—C18	−178.3 (2)
C2—C3—C4—C10	178.8 (3)	C27—N3—C21—C22	178.8 (2)
C9—C3—C4—C10	−3.3 (5)	C27—N3—C21—C26	−0.5 (4)
C3—C4—C5—C6	−0.5 (5)	C26—C21—C22—C23	0.2 (4)
C10—C4—C5—C6	179.2 (3)	N3—C21—C22—C23	−179.1 (2)
C2—C1—C6—C5	−1.4 (4)	C21—C22—C23—C24	−0.1 (4)
N1—C1—C6—C5	−177.3 (3)	C21—C22—C23—C29	179.6 (3)
C4—C5—C6—C1	2.0 (5)	C22—C23—C24—C25	−0.1 (4)
C1—N1—C7—O1	−4.0 (5)	C29—C23—C24—C25	−179.9 (3)
C1—N1—C7—C8	175.1 (2)	C22—C23—C24—C30	−179.9 (3)
C17—N2—C11—C16	7.9 (4)	C29—C23—C24—C30	0.4 (4)
C17—N2—C11—C12	−173.6 (3)	C23—C24—C25—C26	0.3 (5)
C16—C11—C12—C13	−2.1 (4)	C30—C24—C25—C26	−179.9 (3)
N2—C11—C12—C13	179.3 (2)	C24—C25—C26—C21	−0.3 (5)
C11—C12—C13—C14	−0.4 (4)	C22—C21—C26—C25	0.0 (4)
C11—C12—C13—C19	178.2 (3)	N3—C21—C26—C25	179.3 (3)
C12—C13—C14—C15	2.1 (4)	C21—N3—C27—O3	0.7 (4)
C19—C13—C14—C15	−176.5 (3)	C21—N3—C27—C28	−178.2 (3)
C12—C13—C14—C20	−178.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.88 (3)	2.08 (3)	2.956 (3)	177 (3)
N3—H3N···O2	0.86 (3)	2.14 (3)	2.989 (3)	172 (3)
N2—H2N···O1ⁱ	0.98 (3)	1.92 (3)	2.893 (3)	170 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO
M_r	163.21
Crystal system, space group	Triclinic, P1
Temperature (K)	299
a, b, c (Å)	6.749 (1), 14.281 (2), 15.005 (2)
α, β, γ (°)	85.33 (1), 79.81 (1), 87.58 (1)
V (Å³)	1418.1 (3)
Z	6
Radiation type	Cu Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.35 × 0.33 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5528, 5025, 3386
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.210, 1.03
No. of reflections	5025
No. of parameters	344
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

Computer programs: CAD-4-PC Version (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3	0.88 (3)	2.08 (3)	2.956 (3)	177 (3)
N3—H3N···O2	0.86 (3)	2.14 (3)	2.989 (3)	172 (3)
N2—H2N···O1ⁱ	0.98 (3)	1.92 (3)	2.893 (3)	170 (2)

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

Acknowledgements

B.T.G. thanks the Alexander von Humboldt Foundation, Bonn, Germany for extensions of his research fellowship.

References

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