N-(3,4-Dimethyl­phen­yl)-4-methyl­benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Rodrigues, V.Z.; Fuess, H.

doi:10.1107/S1600536809041257

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2751

https://doi.org/10.1107/S1600536809041257

Open

access

N-(3,4-Dimethylphenyl)-4-methylbenzamide

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b Vinola Zeena Rodrigues ^a and Hartmut Fuess ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bFaculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic, and ^cInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 8 October 2009; accepted 9 October 2009; online 17 October 2009)

The title compound, C₁₆H₁₇NO, crystallizes with two molecules in the asymmetric unit. The conformation of the N—H bond is anti to the meta-methyl substituent in the aniline ring in the first molecule and syn in the second molecule. The dihedral angles between the two benzene rings are 52.6 (1) and 10.5 (1)° in the first and second molecules, respectively. Intermolecular N—H⋯O hydrogen bonds link the molecules into chains running along the b axis of the crystal.

Related literature

For the preparation of the title compound, see: Gowda et al. (2003 ). For related structures, see: Bowes et al. (2003 ); Gowda et al. (2008 , 2009 ).

Experimental

Crystal data

C₁₆H₁₇NO
M_r = 239.31
Triclinic, $[P \overline 1]$
a = 9.4186 (3) Å
b = 9.55915 (18) Å
c = 15.8813 (4) Å
α = 74.361 (2)°
β = 79.696 (2)°
γ = 88.1582 (18)°
V = 1354.51 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.51 × 0.41 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby Gemini detector
Absorption correction: multi-scan (CrysAlis Pro; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.943, T_max = 0.981
24655 measured reflections
5130 independent reflections
3880 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.126
S = 1.09
5130 reflections
332 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.86	2.29	3.0860 (14)	154
N2—H2N⋯O1ⁱⁱ	0.86	2.18	3.0101 (14)	162
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: CrysAlis Pro (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809041257/bt5089sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041257/bt5089Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the crystal structures of benzanilides (Gowda, Tokarčík et al., 2008, 2009), the structure of N-(3,4-dimethylphenyl)4-methylbenzamide (I) has been determined. In the structure, the conformations of the N—H and C=O bonds are anti to each other (Fig. 1), similar to those observed in N-(3,4-dimethylphenyl)benzamide (Gowda, Tokarčík et al., 2008), N-(2,6-dimethylphenyl)4-methylbenzamide (Gowda, Tokarčík et al., 2009) and the parent benzanilide (Bowes et al., 2003).

The asymmetric unit of the cell in (I) contains two independent molecules. In the first molecule, the conformation of the N—H bond is anti to the meta-methyl-substituent in the disubstituted phenyl ring, while in the second molecule this conformation is syn. The dihedral angles between the two benzene rings are 52.6 (1)° and 10.5 (1)° in the first and second molecules, respectively. The central amido group –NH—C(=O)- forms dihedral angles of 22.2 (2)° and 31.2 (1)° with the benzoyl ring, and 30.6 (1)° and 25.5 (1)° with the disubstituted phenyl ring, in the two independent molecules.

The packing diagram of molecules in (I) showing the intermolecular N–H···O hydrogen bonds (Table 1) involved in the formation of molecular chains running along the b-axis is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Gowda et al. (2003). For related structures, see: Bowes et al. (2003); Gowda, Tokarčík et al. (2008, 2009).

Experimental top

The title compound was prepared according to the literature method (Gowda et al., 2003). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra. Single crystals of the title compound used in X-ray diffraction studies were obtained from a slow evaporation of its ethanolic solution at room temperature.

Structure description top

The packing diagram of molecules in (I) showing the intermolecular N–H···O hydrogen bonds (Table 1) involved in the formation of molecular chains running along the b-axis is shown in Fig. 2.

For the preparation of the title compound, see: Gowda et al. (2003). For related structures, see: Bowes et al. (2003); Gowda, Tokarčík et al. (2008, 2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of 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. Part of the crystal structure of the title compound. Molecular chains running along the b-axis are generated by N–H···O hydrogen bonds, shown as dashed lines. Symmetry codes (i): -x + 1,-y,-z + 1; (ii) -x + 1,-y + 1,-z + 1. H atoms not involved in hydrogen bonding are omitted.

N-(3,4-Dimethylphenyl)-4-methylbenzamide top

Crystal data top

C₁₆H₁₇NO	Z = 4
M_r = 239.31	F(000) = 512
Triclinic, P1	D_x = 1.173 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.4186 (3) Å	Cell parameters from 13000 reflections
b = 9.55915 (18) Å	θ = 2.2–29.3°
c = 15.8813 (4) Å	µ = 0.07 mm⁻¹
α = 74.361 (2)°	T = 295 K
β = 79.696 (2)°	Block, colourless
γ = 88.1582 (18)°	0.51 × 0.41 × 0.22 mm
V = 1354.51 (6) Å³

Data collection top

Oxford Diffraction Xcalibur with a Ruby Gemini detector diffractometer	5130 independent reflections
Graphite monochromator	3880 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.016
ω scans	θ_max = 25.7°, θ_min = 2.2°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −11→11
T_min = 0.943, T_max = 0.981	k = −11→11
24655 measured reflections	l = −19→19

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) = 0.126	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0705P)² + 0.0954P] where P = (F_o² + 2F_c²)/3
5130 reflections	(Δ/σ)_max < 0.001
332 parameters	Δρ_max = 0.19 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₆H₁₇NO	γ = 88.1582 (18)°
M_r = 239.31	V = 1354.51 (6) Å³
Triclinic, P1	Z = 4
a = 9.4186 (3) Å	Mo Kα radiation
b = 9.55915 (18) Å	µ = 0.07 mm⁻¹
c = 15.8813 (4) Å	T = 295 K
α = 74.361 (2)°	0.51 × 0.41 × 0.22 mm
β = 79.696 (2)°

Data collection top

Oxford Diffraction Xcalibur with a Ruby Gemini detector diffractometer	5130 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3880 reflections with I > 2σ(I)
T_min = 0.943, T_max = 0.981	R_int = 0.016
24655 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.09	Δρ_max = 0.19 e Å⁻³
5130 reflections	Δρ_min = −0.13 e Å⁻³
332 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)
C1	0.10346 (14)	0.30182 (13)	0.21469 (9)	0.0465 (3)
C2	0.11199 (14)	0.43910 (14)	0.15658 (9)	0.0488 (3)
H2	0.1996	0.4899	0.1399	0.059*
C3	−0.00845 (15)	0.50305 (14)	0.12241 (9)	0.0502 (3)
C4	−0.13954 (15)	0.42676 (15)	0.14676 (10)	0.0536 (4)
C5	−0.14410 (15)	0.28750 (16)	0.20304 (10)	0.0571 (4)
H5	−0.2303	0.2345	0.2184	0.069*
C6	−0.02543 (15)	0.22486 (15)	0.23707 (10)	0.0538 (4)
H6	−0.0322	0.1313	0.2749	0.065*
C7	0.32980 (14)	0.30304 (13)	0.27355 (9)	0.0483 (3)
C8	0.43956 (14)	0.20801 (13)	0.31706 (9)	0.0464 (3)
C9	0.51877 (16)	0.26395 (15)	0.36612 (10)	0.0569 (4)
H9	0.5038	0.3591	0.3695	0.068*
C10	0.61908 (16)	0.18210 (16)	0.40995 (10)	0.0601 (4)
H10	0.6691	0.2219	0.4437	0.072*
C11	0.64706 (15)	0.04163 (15)	0.40481 (10)	0.0549 (4)
C12	0.57052 (16)	−0.01379 (15)	0.35434 (11)	0.0603 (4)
H12	0.5887	−0.1076	0.3491	0.072*
C13	0.46711 (16)	0.06721 (14)	0.31119 (10)	0.0554 (4)
H13	0.416	0.027	0.2782	0.067*
C14	0.00537 (19)	0.65361 (16)	0.06181 (11)	0.0678 (4)
H14A	0.1056	0.6805	0.0424	0.102*
H14B	−0.0423	0.7201	0.0929	0.102*
H14C	−0.0384	0.6569	0.0112	0.102*
C15	−0.27382 (18)	0.4940 (2)	0.11380 (14)	0.0790 (5)
H15A	−0.287	0.5882	0.1243	0.118*
H15B	−0.3562	0.433	0.1449	0.118*
H15C	−0.2636	0.5034	0.0513	0.118*
C16	0.75981 (18)	−0.04604 (19)	0.45196 (12)	0.0738 (5)
H16A	0.819	0.0174	0.4694	0.111*	0.5
H16B	0.819	−0.094	0.4127	0.111*	0.5
H16C	0.7132	−0.1173	0.5038	0.111*	0.5
H16D	0.7484	−0.1466	0.4546	0.111*	0.5
H16E	0.7484	−0.0353	0.5112	0.111*	0.5
H16F	0.8542	−0.012	0.4201	0.111*	0.5
N1	0.22333 (12)	0.23479 (11)	0.25316 (8)	0.0522 (3)
H1N	0.2277	0.1417	0.2643	0.063*
O1	0.33726 (11)	0.43667 (9)	0.25845 (7)	0.0638 (3)
C21	0.74411 (15)	0.18251 (13)	0.82751 (10)	0.0510 (3)
C22	0.64037 (16)	0.22586 (15)	0.88897 (10)	0.0549 (4)
H22	0.5795	0.3012	0.8688	0.066*
C23	0.62458 (16)	0.16037 (16)	0.97944 (10)	0.0585 (4)
C24	0.71696 (18)	0.04716 (15)	1.00955 (10)	0.0626 (4)
C25	0.81944 (19)	0.00514 (16)	0.94732 (11)	0.0651 (4)
H25	0.8804	−0.0704	0.9671	0.078*
C26	0.83512 (17)	0.07014 (15)	0.85765 (11)	0.0605 (4)
H26	0.9056	0.0393	0.8178	0.073*
C27	0.81041 (15)	0.21391 (14)	0.66478 (10)	0.0513 (3)
C28	0.81065 (15)	0.32107 (14)	0.57693 (9)	0.0490 (3)
C29	0.91799 (16)	0.31421 (16)	0.50555 (11)	0.0575 (4)
H29	0.987	0.2423	0.5134	0.069*
C30	0.92379 (17)	0.41186 (17)	0.42359 (11)	0.0621 (4)
H30	0.9981	0.4065	0.3774	0.074*
C31	0.82068 (18)	0.51821 (16)	0.40875 (10)	0.0598 (4)
C32	0.71185 (18)	0.52273 (16)	0.47904 (10)	0.0612 (4)
H32	0.6403	0.5918	0.4703	0.073*
C33	0.70702 (16)	0.42699 (15)	0.56190 (10)	0.0567 (4)
H33	0.6334	0.4335	0.6082	0.068*
C34	0.5104 (2)	0.2114 (2)	1.04295 (12)	0.0811 (5)
H34A	0.5544	0.2391	1.0863	0.122*
H34B	0.4413	0.1343	1.0724	0.122*
H34C	0.4627	0.2934	1.0108	0.122*
C35	0.7065 (2)	−0.0265 (2)	1.10752 (12)	0.0877 (6)
H35A	0.7735	−0.1047	1.1154	0.132*
H35B	0.6102	−0.0641	1.1319	0.132*
H35C	0.729	0.0427	1.1374	0.132*
C36	0.8276 (2)	0.6250 (2)	0.31868 (12)	0.0885 (6)
H36A	0.9105	0.6056	0.2788	0.133*	0.5
H36B	0.8349	0.722	0.324	0.133*	0.5
H36C	0.7418	0.6152	0.2959	0.133*	0.5
H36D	0.7476	0.6896	0.3203	0.133*	0.5
H36E	0.8232	0.5732	0.2751	0.133*	0.5
H36F	0.9164	0.68	0.3033	0.133*	0.5
N2	0.75630 (13)	0.26110 (11)	0.73672 (8)	0.0549 (3)
H2N	0.7257	0.3488	0.7264	0.066*
O2	0.85769 (12)	0.09069 (10)	0.67005 (7)	0.0667 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0471 (7)	0.0423 (7)	0.0512 (8)	0.0065 (6)	−0.0090 (6)	−0.0149 (6)
C2	0.0438 (7)	0.0467 (7)	0.0571 (8)	−0.0020 (6)	−0.0106 (6)	−0.0144 (6)
C3	0.0564 (8)	0.0446 (7)	0.0529 (8)	0.0033 (6)	−0.0142 (7)	−0.0158 (6)
C4	0.0478 (8)	0.0568 (8)	0.0618 (9)	0.0048 (6)	−0.0153 (7)	−0.0223 (7)
C5	0.0457 (8)	0.0577 (8)	0.0681 (10)	−0.0055 (7)	−0.0070 (7)	−0.0183 (7)
C6	0.0537 (8)	0.0452 (7)	0.0590 (9)	−0.0006 (6)	−0.0042 (7)	−0.0115 (6)
C7	0.0518 (8)	0.0403 (6)	0.0518 (8)	0.0060 (6)	−0.0073 (6)	−0.0123 (6)
C8	0.0447 (7)	0.0406 (7)	0.0491 (8)	0.0056 (6)	−0.0035 (6)	−0.0078 (6)
C9	0.0590 (9)	0.0468 (7)	0.0689 (10)	0.0088 (7)	−0.0138 (7)	−0.0215 (7)
C10	0.0569 (9)	0.0615 (9)	0.0638 (10)	0.0040 (7)	−0.0158 (7)	−0.0171 (7)
C11	0.0454 (8)	0.0547 (8)	0.0542 (8)	0.0054 (6)	−0.0045 (6)	−0.0004 (7)
C12	0.0628 (9)	0.0410 (7)	0.0742 (10)	0.0126 (7)	−0.0124 (8)	−0.0114 (7)
C13	0.0561 (8)	0.0461 (7)	0.0661 (9)	0.0083 (6)	−0.0155 (7)	−0.0162 (7)
C14	0.0778 (11)	0.0526 (8)	0.0736 (11)	0.0044 (8)	−0.0314 (9)	−0.0069 (8)
C15	0.0593 (10)	0.0817 (11)	0.1008 (14)	0.0088 (9)	−0.0308 (9)	−0.0226 (10)
C16	0.0613 (10)	0.0733 (10)	0.0743 (11)	0.0121 (8)	−0.0174 (8)	0.0035 (9)
N1	0.0549 (7)	0.0350 (5)	0.0658 (8)	0.0044 (5)	−0.0144 (6)	−0.0101 (5)
O1	0.0730 (7)	0.0377 (4)	0.0875 (8)	0.0087 (5)	−0.0319 (6)	−0.0175 (5)
C21	0.0560 (8)	0.0375 (6)	0.0605 (9)	−0.0002 (6)	−0.0165 (7)	−0.0106 (6)
C22	0.0542 (8)	0.0464 (7)	0.0659 (10)	0.0028 (6)	−0.0163 (7)	−0.0148 (7)
C23	0.0608 (9)	0.0524 (8)	0.0644 (10)	−0.0087 (7)	−0.0128 (7)	−0.0168 (7)
C24	0.0765 (10)	0.0475 (8)	0.0630 (10)	−0.0104 (7)	−0.0211 (8)	−0.0063 (7)
C25	0.0776 (11)	0.0451 (8)	0.0720 (11)	0.0081 (7)	−0.0262 (9)	−0.0072 (7)
C26	0.0673 (10)	0.0451 (7)	0.0689 (10)	0.0092 (7)	−0.0175 (8)	−0.0124 (7)
C27	0.0501 (8)	0.0401 (7)	0.0668 (9)	0.0054 (6)	−0.0163 (7)	−0.0163 (6)
C28	0.0500 (8)	0.0417 (7)	0.0604 (9)	0.0033 (6)	−0.0162 (7)	−0.0185 (6)
C29	0.0523 (8)	0.0555 (8)	0.0726 (10)	0.0107 (7)	−0.0161 (7)	−0.0287 (8)
C30	0.0642 (10)	0.0676 (9)	0.0596 (9)	−0.0015 (8)	−0.0054 (8)	−0.0291 (8)
C31	0.0743 (10)	0.0550 (8)	0.0552 (9)	0.0011 (7)	−0.0147 (8)	−0.0215 (7)
C32	0.0705 (10)	0.0540 (8)	0.0600 (9)	0.0164 (7)	−0.0172 (8)	−0.0152 (7)
C33	0.0595 (9)	0.0520 (8)	0.0577 (9)	0.0122 (7)	−0.0082 (7)	−0.0157 (7)
C34	0.0821 (12)	0.0884 (12)	0.0752 (12)	−0.0012 (10)	−0.0092 (9)	−0.0289 (10)
C35	0.1162 (16)	0.0751 (11)	0.0675 (11)	−0.0026 (11)	−0.0260 (11)	−0.0052 (9)
C36	0.1194 (16)	0.0842 (12)	0.0585 (11)	0.0085 (11)	−0.0133 (10)	−0.0158 (9)
N2	0.0663 (8)	0.0392 (6)	0.0596 (7)	0.0121 (5)	−0.0157 (6)	−0.0123 (5)
O2	0.0815 (7)	0.0407 (5)	0.0802 (7)	0.0160 (5)	−0.0193 (6)	−0.0187 (5)

Geometric parameters (Å, º) top

C1—C6	1.3796 (19)	C21—C26	1.3885 (19)
C1—C2	1.3812 (18)	C21—C22	1.389 (2)
C1—N1	1.4309 (16)	C21—N2	1.4209 (18)
C2—C3	1.3970 (18)	C22—C23	1.387 (2)
C2—H2	0.93	C22—H22	0.93
C3—C4	1.393 (2)	C23—C24	1.402 (2)
C3—C14	1.495 (2)	C23—C34	1.501 (2)
C4—C5	1.386 (2)	C24—C25	1.385 (2)
C4—C15	1.513 (2)	C24—C35	1.512 (2)
C5—C6	1.378 (2)	C25—C26	1.375 (2)
C5—H5	0.93	C25—H25	0.93
C6—H6	0.93	C26—H26	0.93
C7—O1	1.2364 (15)	C27—O2	1.2326 (15)
C7—N1	1.3448 (17)	C27—N2	1.3502 (18)
C7—C8	1.4927 (18)	C27—C28	1.491 (2)
C8—C9	1.3812 (19)	C28—C33	1.3872 (19)
C8—C13	1.3871 (18)	C28—C29	1.392 (2)
C9—C10	1.372 (2)	C29—C30	1.375 (2)
C9—H9	0.93	C29—H29	0.93
C10—C11	1.381 (2)	C30—C31	1.386 (2)
C10—H10	0.93	C30—H30	0.93
C11—C12	1.380 (2)	C31—C32	1.383 (2)
C11—C16	1.510 (2)	C31—C36	1.508 (2)
C12—C13	1.3863 (19)	C32—C33	1.380 (2)
C12—H12	0.93	C32—H32	0.93
C13—H13	0.93	C33—H33	0.93
C14—H14A	0.96	C34—H34A	0.96
C14—H14B	0.96	C34—H34B	0.96
C14—H14C	0.96	C34—H34C	0.96
C15—H15A	0.96	C35—H35A	0.96
C15—H15B	0.96	C35—H35B	0.96
C15—H15C	0.96	C35—H35C	0.96
C16—H16A	0.96	C36—H36A	0.96
C16—H16B	0.96	C36—H36B	0.96
C16—H16C	0.96	C36—H36C	0.96
C16—H16D	0.96	C36—H36D	0.96
C16—H16E	0.96	C36—H36E	0.96
C16—H16F	0.96	C36—H36F	0.96
N1—H1N	0.86	N2—H2N	0.86

C6—C1—C2	119.20 (12)	C26—C21—C22	118.95 (14)
C6—C1—N1	118.01 (11)	C26—C21—N2	123.14 (13)
C2—C1—N1	122.79 (12)	C22—C21—N2	117.83 (12)
C1—C2—C3	121.25 (12)	C23—C22—C21	122.13 (13)
C1—C2—H2	119.4	C23—C22—H22	118.9
C3—C2—H2	119.4	C21—C22—H22	118.9
C4—C3—C2	119.52 (12)	C22—C23—C24	118.70 (14)
C4—C3—C14	121.29 (13)	C22—C23—C34	119.93 (14)
C2—C3—C14	119.17 (13)	C24—C23—C34	121.37 (15)
C5—C4—C3	118.06 (12)	C25—C24—C23	118.36 (14)
C5—C4—C15	120.72 (14)	C25—C24—C35	120.60 (15)
C3—C4—C15	121.22 (13)	C23—C24—C35	121.03 (16)
C6—C5—C4	122.34 (13)	C26—C25—C24	122.92 (14)
C6—C5—H5	118.8	C26—C25—H25	118.5
C4—C5—H5	118.8	C24—C25—H25	118.5
C5—C6—C1	119.57 (13)	C25—C26—C21	118.94 (15)
C5—C6—H6	120.2	C25—C26—H26	120.5
C1—C6—H6	120.2	C21—C26—H26	120.5
O1—C7—N1	122.74 (12)	O2—C27—N2	122.99 (13)
O1—C7—C8	121.06 (12)	O2—C27—C28	121.21 (13)
N1—C7—C8	116.20 (11)	N2—C27—C28	115.80 (11)
C9—C8—C13	117.98 (12)	C33—C28—C29	117.72 (13)
C9—C8—C7	117.90 (11)	C33—C28—C27	123.19 (13)
C13—C8—C7	124.11 (12)	C29—C28—C27	119.08 (12)
C10—C9—C8	121.37 (13)	C30—C29—C28	121.18 (13)
C10—C9—H9	119.3	C30—C29—H29	119.4
C8—C9—H9	119.3	C28—C29—H29	119.4
C9—C10—C11	121.13 (14)	C29—C30—C31	121.05 (14)
C9—C10—H10	119.4	C29—C30—H30	119.5
C11—C10—H10	119.4	C31—C30—H30	119.5
C12—C11—C10	117.77 (13)	C32—C31—C30	117.79 (14)
C12—C11—C16	121.72 (14)	C32—C31—C36	121.41 (15)
C10—C11—C16	120.50 (15)	C30—C31—C36	120.79 (15)
C11—C12—C13	121.47 (13)	C33—C32—C31	121.46 (14)
C11—C12—H12	119.3	C33—C32—H32	119.3
C13—C12—H12	119.3	C31—C32—H32	119.3
C12—C13—C8	120.26 (13)	C32—C33—C28	120.77 (14)
C12—C13—H13	119.9	C32—C33—H33	119.6
C8—C13—H13	119.9	C28—C33—H33	119.6
C3—C14—H14A	109.5	C23—C34—H34A	109.5
C3—C14—H14B	109.5	C23—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C3—C14—H14C	109.5	C23—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C4—C15—H15A	109.5	C24—C35—H35A	109.5
C4—C15—H15B	109.5	C24—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C4—C15—H15C	109.5	C24—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
C11—C16—H16A	109.5	C31—C36—H36A	109.5
C11—C16—H16B	109.5	C31—C36—H36B	109.5
H16A—C16—H16B	109.5	H36A—C36—H36B	109.5
C11—C16—H16C	109.5	C31—C36—H36C	109.5
H16A—C16—H16C	109.5	H36A—C36—H36C	109.5
H16B—C16—H16C	109.5	H36B—C36—H36C	109.5
C11—C16—H16D	109.5	C31—C36—H36D	109.5
H16A—C16—H16D	141.1	H36A—C36—H36D	141.1
H16B—C16—H16D	56.3	H36B—C36—H36D	56.3
H16C—C16—H16D	56.3	H36C—C36—H36D	56.3
C11—C16—H16E	109.5	C31—C36—H36E	109.5
H16A—C16—H16E	56.3	H36A—C36—H36E	56.3
H16B—C16—H16E	141.1	H36B—C36—H36E	141.1
H16C—C16—H16E	56.3	H36C—C36—H36E	56.3
H16D—C16—H16E	109.5	H36D—C36—H36E	109.5
C11—C16—H16F	109.5	C31—C36—H36F	109.5
H16A—C16—H16F	56.3	H36A—C36—H36F	56.3
H16B—C16—H16F	56.3	H36B—C36—H36F	56.3
H16C—C16—H16F	141.1	H36C—C36—H36F	141.1
H16D—C16—H16F	109.5	H36D—C36—H36F	109.5
H16E—C16—H16F	109.5	H36E—C36—H36F	109.5
C7—N1—C1	126.38 (10)	C27—N2—C21	127.45 (11)
C7—N1—H1N	116.8	C27—N2—H2N	116.3
C1—N1—H1N	116.8	C21—N2—H2N	116.3

C6—C1—C2—C3	2.1 (2)	C26—C21—C22—C23	−0.1 (2)
N1—C1—C2—C3	−177.99 (11)	N2—C21—C22—C23	−177.00 (12)
C1—C2—C3—C4	−0.5 (2)	C21—C22—C23—C24	0.3 (2)
C1—C2—C3—C14	178.23 (13)	C21—C22—C23—C34	−179.90 (14)
C2—C3—C4—C5	−1.4 (2)	C22—C23—C24—C25	−0.4 (2)
C14—C3—C4—C5	179.87 (14)	C34—C23—C24—C25	179.74 (15)
C2—C3—C4—C15	177.87 (14)	C22—C23—C24—C35	178.91 (14)
C14—C3—C4—C15	−0.8 (2)	C34—C23—C24—C35	−0.9 (2)
C3—C4—C5—C6	1.8 (2)	C23—C24—C25—C26	0.5 (2)
C15—C4—C5—C6	−177.47 (14)	C35—C24—C25—C26	−178.86 (15)
C4—C5—C6—C1	−0.3 (2)	C24—C25—C26—C21	−0.3 (2)
C2—C1—C6—C5	−1.7 (2)	C22—C21—C26—C25	0.2 (2)
N1—C1—C6—C5	178.37 (12)	N2—C21—C26—C25	176.86 (13)
O1—C7—C8—C9	21.3 (2)	O2—C27—C28—C33	148.70 (14)
N1—C7—C8—C9	−157.96 (13)	N2—C27—C28—C33	−31.60 (19)
O1—C7—C8—C13	−158.56 (14)	O2—C27—C28—C29	−30.15 (19)
N1—C7—C8—C13	22.2 (2)	N2—C27—C28—C29	149.55 (13)
C13—C8—C9—C10	−1.8 (2)	C33—C28—C29—C30	2.0 (2)
C7—C8—C9—C10	178.34 (13)	C27—C28—C29—C30	−179.12 (13)
C8—C9—C10—C11	1.6 (2)	C28—C29—C30—C31	−1.6 (2)
C9—C10—C11—C12	−0.2 (2)	C29—C30—C31—C32	0.0 (2)
C9—C10—C11—C16	178.81 (14)	C29—C30—C31—C36	−179.97 (14)
C10—C11—C12—C13	−1.0 (2)	C30—C31—C32—C33	1.4 (2)
C16—C11—C12—C13	180.00 (14)	C36—C31—C32—C33	−178.70 (16)
C11—C12—C13—C8	0.8 (2)	C31—C32—C33—C28	−1.0 (2)
C9—C8—C13—C12	0.6 (2)	C29—C28—C33—C32	−0.6 (2)
C7—C8—C13—C12	−179.55 (13)	C27—C28—C33—C32	−179.50 (13)
O1—C7—N1—C1	−1.9 (2)	O2—C27—N2—C21	0.1 (2)
C8—C7—N1—C1	177.33 (12)	C28—C27—N2—C21	−179.59 (12)
C6—C1—N1—C7	−148.38 (14)	C26—C21—N2—C27	27.1 (2)
C2—C1—N1—C7	31.7 (2)	C22—C21—N2—C27	−156.12 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86	2.29	3.0860 (14)	154
N2—H2N···O1ⁱⁱ	0.86	2.18	3.0101 (14)	162

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO
M_r	239.31
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.4186 (3), 9.55915 (18), 15.8813 (4)
α, β, γ (°)	74.361 (2), 79.696 (2), 88.1582 (18)
V (Å³)	1354.51 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.51 × 0.41 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur with a Ruby Gemini detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.943, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	24655, 5130, 3880
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.126, 1.09
No. of reflections	5130
No. of parameters	332
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.13

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.86	2.29	3.0860 (14)	154
N2—H2N···O1ⁱⁱ	0.86	2.18	3.0101 (14)	162

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1.

Acknowledgements

MT and JK thank the Grant Agency of the Slovak Republic (VEGA 1/0817/08) and Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.

References

Bowes, K. F., Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2003). Acta Cryst. C59, o1–o3. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (2002). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2009). Acta Cryst. E65, o1612. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis Pro. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar