N-(2,6-Dimethyl­phen­yl)benzamide

Gowda, B.T.; Tokarčík, M.; Kožíšek, J.; Sowmya, B.P.; Fuess, H.

doi:10.1107/S1600536808018230

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1299

doi:10.1107/S1600536808018230

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N-(2,6-Dimethylphenyl)benzamide

B. Thimme Gowda,^a ^* Miroslav Tokarčík,^b Jozef Kožíšek,^b B. P. Sowmya ^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 10 June 2008; accepted 16 June 2008; online 19 June 2008)

The title compound, C₁₅H₁₅NO, crystallizes with two molecules in the asymmetric unit. The H—N—C=O units are in a trans conformation, similar to that observed in N-(3,4-dimethylphenyl)benzamide, N-(2,6-dichlorophenyl)benzamide and other benzanilides. The central –NHCO– bridging unit is tilted at angles of 17.1 (3) and 16.4 (3)° to the benzoyl ring in the two molecules. The two rings (benzoyl and aniline) are almost orthogonal with respect to each other, making dihedral angles of 86.3 (1) and 86.0 (1)° in the two molecules. N—H⋯O hydrogen bonds link molecules into infinite chains running along the c axis.

Related literature

For related literature, see: Gowda et al. (2003 , 2008a ,b ).

Experimental

Crystal data

C₁₅H₁₅NO
M_r = 225.28
Monoclinic, P c
a = 16.4389 (8) Å
b = 8.2903 (4) Å
c = 9.4902 (3) Å
β = 98.165 (4)°
V = 1280.25 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 (2) K
0.52 × 0.46 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.924, T_max = 0.985
38015 measured reflections
2504 independent reflections
2110 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 0.98
2504 reflections
307 parameters
35 restraints
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86	2.19	2.949 (2)	147
N2—H2N⋯O2ⁱⁱ	0.86	2.17	2.949 (2)	150
Symmetry codes: (i) $[x, -y, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); 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 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2002 ); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003 ) and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018230/bt2724sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018230/bt2724Isup2.hkl

checkCIF report

Comment top

In the present work, the structure of N-(2,6-dimethylphenyl)-benzamide (N26DMPBA) has been determined to study the effect of substituents on the solid state geometries of benzanilides (Gowda et al., 2003; Gowda et al., 2008a; Gowda et al., 2008b). The conformations of the N—H and C=O bonds in N26DMPBA (Fig.1) are anti to each other, similar to that observed in N-(3,4-dimethylphenyl)-benzamide (Gowda et al., 2008a), N-(2,6-dichlorophenyl)-benzamide (Gowda et al., 2008b) and other benzanilides (Gowda et al., 2003). The structure of N26DMPBA has two molecules in its asymmetric unit. The central amide group –NHCO– is tilted to the benzoyl ring at the angles of 17.1 (3)° and 16.4 (3)°, in molecule 1 and 2, respectively. The two rings (benzoyl and aniline) are almost orthogonal, with the dihedral angles of 86.3 (1)° and 86.0 (1)° in molecules 1 and 2, respectively.

Part of the crystal structure of the title compound showing molecular chains as viewed down the b axis is shown in Fig.2. Hydrogen bonds N1–H1N···O1(i) and N2–H2N···O2(ii) give rise to infinite molecular chains running along the c axis (Symmetry codes: (i) x,-y,z + 1/2; (ii) x,-y + 1,z + 1/2).

Related literature top

For related literature, see: Gowda et al. (2003, 2008a,b).

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 were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); 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 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Crystal structure of the title compound viewed down the b axis. Hydrogen bonds N1–H1N···O1(i) and N2–H2N···O2(ii) give rise to infinite molecular chains running along the c axis. Symmetry codes: (i) x,-y,z + 1/2; (ii) x,-y + 1,z + 1/2. H atoms not involved in hydrogen bonding are omitted.

N-(2,6-Dimethylphenyl)benzamide top

Crystal data top

C₁₅H₁₅NO	F(000) = 480
M_r = 225.28	D_x = 1.169 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2 y c	Cell parameters from 18913 reflections
a = 16.4389 (8) Å	θ = 3.1–29.3°
b = 8.2903 (4) Å	µ = 0.07 mm⁻¹
c = 9.4902 (3) Å	T = 295 K
β = 98.165 (4)°	Block, colourless
V = 1280.25 (10) Å³	0.52 × 0.46 × 0.22 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer	2504 independent reflections
Graphite monochromator	2110 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.059
ω scans with κ offsets	θ_max = 26.0°, θ_min = 5.3°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −20→20
T_min = 0.924, T_max = 0.985	k = −10→10
38015 measured reflections	l = −11→11

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0851P)²] where P = (F_o² + 2F_c²)/3
S = 0.98	(Δ/σ)_max = 0.001
2504 reflections	Δρ_max = 0.13 e Å⁻³
307 parameters	Δρ_min = −0.14 e Å⁻³
35 restraints	Absolute structure: Flack (1983), 2493 Friedel pairs
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₅H₁₅NO	V = 1280.25 (10) Å³
M_r = 225.28	Z = 4
Monoclinic, Pc	Mo Kα radiation
a = 16.4389 (8) Å	µ = 0.07 mm⁻¹
b = 8.2903 (4) Å	T = 295 K
c = 9.4902 (3) Å	0.52 × 0.46 × 0.22 mm
β = 98.165 (4)°

Data collection top

Oxford Diffraction Xcalibur diffractometer	2504 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	2110 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.985	R_int = 0.059
38015 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	35 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 0.98	Δρ_max = 0.13 e Å⁻³
2504 reflections	Δρ_min = −0.14 e Å⁻³
307 parameters	Absolute structure: Flack (1983), 2493 Friedel pairs

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
N1	0.32493 (12)	0.0027 (2)	0.63912 (17)	0.0476 (4)
H1N	0.324	−0.0067	0.7291	0.057*
O1	0.27687 (12)	−0.0838 (2)	0.41847 (15)	0.0654 (5)
C1	0.27534 (13)	−0.0900 (2)	0.5470 (2)	0.0446 (5)
C2	0.21752 (13)	−0.2015 (2)	0.6052 (2)	0.0435 (5)
C3	0.15307 (16)	−0.2637 (3)	0.5109 (2)	0.0523 (5)
H3	0.1478	−0.2349	0.4153	0.063*
C4	0.09687 (16)	−0.3669 (3)	0.5561 (3)	0.0601 (6)
H4	0.0532	−0.4056	0.492	0.072*
C5	0.10537 (18)	−0.4130 (3)	0.6967 (3)	0.0664 (7)
H5	0.0679	−0.4843	0.7276	0.08*
C6	0.16901 (17)	−0.3537 (3)	0.7909 (3)	0.0655 (7)
H6	0.1745	−0.3852	0.8859	0.079*
C7	0.22549 (17)	−0.2472 (3)	0.7468 (2)	0.0534 (5)
H7	0.2683	−0.2068	0.8118	0.064*
C8	0.37898 (15)	0.1165 (3)	0.5877 (2)	0.0523 (5)
C9	0.36263 (18)	0.2796 (3)	0.5956 (3)	0.0611 (6)
C10	0.4128 (2)	0.3869 (4)	0.5370 (4)	0.0872 (10)
H10	0.4028	0.4971	0.5414	0.105*
C11	0.4773 (3)	0.3323 (6)	0.4721 (5)	0.1051 (13)
H11	0.5097	0.4056	0.431	0.126*
C12	0.4940 (2)	0.1719 (6)	0.4678 (4)	0.0922 (10)
H12	0.5382	0.1373	0.4245	0.111*
C13	0.44632 (17)	0.0583 (4)	0.5268 (3)	0.0714 (7)
C14	0.46683 (19)	−0.1163 (3)	0.5241 (4)	0.0916 (10)
H14A	0.5245	−0.1288	0.5198	0.137*
H14B	0.4358	−0.1657	0.4421	0.137*
H14C	0.4535	−0.1671	0.6088	0.137*
C15	0.29134 (19)	0.3401 (3)	0.6634 (3)	0.0813 (8)
H15A	0.3035	0.329	0.7649	0.122*
H15B	0.2817	0.4516	0.6394	0.122*
H15C	0.2432	0.2782	0.6291	0.122*
N2	0.82433 (12)	0.5011 (2)	0.52006 (18)	0.0491 (4)
H2N	0.8272	0.4924	0.6109	0.059*
O2	0.87411 (12)	0.4211 (2)	0.32326 (16)	0.0615 (5)
C21	0.87462 (13)	0.4123 (3)	0.4518 (2)	0.0432 (5)
C22	0.93234 (13)	0.2984 (2)	0.5387 (2)	0.0432 (5)
C23	0.99704 (15)	0.2371 (3)	0.4762 (2)	0.0524 (5)
H23	1.0031	0.268	0.3841	0.063*
C24	1.05223 (16)	0.1314 (3)	0.5484 (3)	0.0617 (6)
H24	1.0959	0.0927	0.5058	0.074*
C25	1.04286 (19)	0.0830 (4)	0.6833 (3)	0.0695 (7)
H25	1.0798	0.0102	0.7319	0.083*
C26	0.9794 (2)	0.1416 (4)	0.7462 (3)	0.0706 (7)
H26	0.9733	0.1089	0.8379	0.085*
C27	0.92362 (17)	0.2497 (3)	0.6748 (2)	0.0552 (6)
H27	0.8805	0.2892	0.7185	0.066*
C28	0.76616 (16)	0.6096 (3)	0.4456 (3)	0.0574 (6)
C29	0.69959 (18)	0.5439 (5)	0.3541 (3)	0.0782 (8)
C30	0.6445 (3)	0.6494 (8)	0.2804 (4)	0.1161 (14)
H30	0.5997	0.6093	0.2198	0.139*
C31	0.6549 (4)	0.8115 (8)	0.2950 (5)	0.1338 (18)
H31	0.6174	0.8807	0.2432	0.161*
C32	0.7200 (3)	0.8750 (5)	0.3850 (5)	0.1149 (14)
H32	0.7256	0.9862	0.3944	0.138*
C33	0.7778 (2)	0.7734 (4)	0.4626 (3)	0.0749 (8)
C34	0.8494 (3)	0.8415 (4)	0.5588 (4)	0.0956 (11)
H34A	0.8985	0.7854	0.5439	0.143*
H34B	0.8406	0.8288	0.6561	0.143*
H34C	0.855	0.954	0.5383	0.143*
C35	0.6868 (2)	0.3667 (5)	0.3381 (4)	0.0944 (11)
H35A	0.6348	0.3462	0.2812	0.142*
H35B	0.6876	0.3186	0.4303	0.142*
H35C	0.73	0.3209	0.2924	0.142*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0636 (11)	0.0502 (11)	0.0299 (8)	−0.0042 (8)	0.0098 (7)	−0.0009 (7)
O1	0.0973 (13)	0.0703 (11)	0.0302 (8)	−0.0220 (9)	0.0143 (8)	−0.0006 (7)
C1	0.0622 (13)	0.0405 (11)	0.0317 (10)	0.0035 (9)	0.0088 (9)	0.0025 (8)
C2	0.0584 (12)	0.0382 (10)	0.0354 (10)	0.0056 (9)	0.0121 (9)	−0.0022 (8)
C3	0.0676 (14)	0.0524 (12)	0.0370 (10)	0.0002 (11)	0.0074 (10)	−0.0012 (9)
C4	0.0624 (14)	0.0608 (15)	0.0580 (14)	−0.0097 (12)	0.0113 (11)	−0.0109 (11)
C5	0.0785 (16)	0.0621 (15)	0.0651 (16)	−0.0169 (13)	0.0318 (13)	−0.0066 (12)
C6	0.0941 (19)	0.0658 (15)	0.0404 (12)	−0.0114 (14)	0.0224 (12)	0.0041 (11)
C7	0.0704 (15)	0.0549 (13)	0.0356 (10)	−0.0044 (11)	0.0096 (10)	0.0001 (9)
C8	0.0583 (12)	0.0603 (14)	0.0375 (11)	−0.0109 (10)	0.0040 (9)	0.0008 (9)
C9	0.0758 (16)	0.0583 (14)	0.0465 (13)	−0.0119 (12)	−0.0011 (11)	0.0019 (10)
C10	0.112 (2)	0.0695 (19)	0.077 (2)	−0.0283 (17)	0.0019 (18)	0.0093 (15)
C11	0.102 (3)	0.116 (3)	0.099 (3)	−0.047 (2)	0.021 (2)	0.018 (2)
C12	0.0732 (18)	0.118 (3)	0.089 (2)	−0.0255 (19)	0.0234 (17)	0.001 (2)
C13	0.0634 (15)	0.090 (2)	0.0615 (16)	−0.0082 (14)	0.0117 (13)	−0.0007 (14)
C14	0.083 (2)	0.097 (2)	0.100 (3)	0.0162 (18)	0.0284 (18)	−0.0079 (19)
C15	0.116 (2)	0.0602 (16)	0.0685 (17)	0.0098 (16)	0.0150 (16)	0.0055 (14)
N2	0.0646 (11)	0.0517 (11)	0.0318 (9)	0.0042 (9)	0.0095 (7)	0.0007 (7)
O2	0.0854 (11)	0.0690 (11)	0.0316 (8)	0.0136 (8)	0.0131 (7)	0.0056 (7)
C21	0.0534 (11)	0.0406 (11)	0.0354 (11)	−0.0037 (9)	0.0056 (9)	0.0006 (8)
C22	0.0566 (12)	0.0389 (10)	0.0337 (10)	−0.0058 (9)	0.0050 (9)	−0.0026 (8)
C23	0.0650 (14)	0.0505 (13)	0.0431 (11)	0.0003 (11)	0.0126 (10)	−0.0022 (9)
C24	0.0620 (14)	0.0627 (15)	0.0594 (14)	0.0096 (12)	0.0054 (11)	−0.0100 (11)
C25	0.0839 (18)	0.0638 (16)	0.0554 (15)	0.0191 (14)	−0.0085 (13)	−0.0017 (12)
C26	0.103 (2)	0.0713 (16)	0.0367 (12)	0.0173 (16)	0.0076 (12)	0.0101 (11)
C27	0.0738 (15)	0.0550 (13)	0.0378 (11)	0.0078 (11)	0.0109 (11)	0.0026 (10)
C28	0.0638 (14)	0.0676 (15)	0.0428 (12)	0.0141 (11)	0.0149 (10)	0.0050 (10)
C29	0.0598 (15)	0.117 (2)	0.0581 (16)	0.0097 (16)	0.0087 (12)	0.0036 (16)
C30	0.083 (2)	0.167 (4)	0.093 (3)	0.041 (3)	−0.006 (2)	0.006 (3)
C31	0.133 (4)	0.157 (4)	0.105 (3)	0.079 (3)	−0.006 (3)	0.026 (3)
C32	0.163 (4)	0.086 (2)	0.098 (3)	0.058 (3)	0.025 (3)	0.015 (2)
C33	0.106 (2)	0.0647 (17)	0.0579 (16)	0.0229 (15)	0.0245 (15)	0.0070 (12)
C34	0.155 (3)	0.0564 (17)	0.078 (2)	−0.009 (2)	0.024 (2)	−0.0030 (15)
C35	0.0733 (19)	0.114 (3)	0.094 (3)	−0.0303 (19)	0.0074 (18)	−0.014 (2)

Geometric parameters (Å, º) top

N1—C1	1.348 (3)	N2—C21	1.341 (3)
N1—C8	1.429 (3)	N2—C28	1.425 (3)
N1—H1N	0.86	N2—H2N	0.86
O1—C1	1.225 (2)	O2—C21	1.221 (3)
C1—C2	1.487 (3)	C21—C22	1.500 (3)
C2—C3	1.385 (3)	C22—C27	1.380 (3)
C2—C7	1.385 (3)	C22—C23	1.386 (3)
C3—C4	1.373 (4)	C23—C24	1.372 (4)
C3—H3	0.93	C23—H23	0.93
C4—C5	1.376 (4)	C24—C25	1.372 (4)
C4—H4	0.93	C24—H24	0.93
C5—C6	1.368 (4)	C25—C26	1.364 (4)
C5—H5	0.93	C25—H25	0.93
C6—C7	1.389 (4)	C26—C27	1.388 (4)
C6—H6	0.93	C26—H26	0.93
C7—H7	0.93	C27—H27	0.93
C8—C9	1.383 (4)	C28—C33	1.378 (4)
C8—C13	1.405 (4)	C28—C29	1.406 (4)
C9—C10	1.382 (4)	C29—C30	1.376 (5)
C9—C15	1.501 (4)	C29—C35	1.489 (6)
C10—C11	1.376 (6)	C30—C31	1.359 (8)
C10—H10	0.93	C30—H30	0.93
C11—C12	1.360 (6)	C31—C32	1.375 (8)
C11—H11	0.93	C31—H31	0.93
C12—C13	1.392 (5)	C32—C33	1.398 (5)
C12—H12	0.93	C32—H32	0.93
C13—C14	1.488 (4)	C33—C34	1.494 (5)
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	0.9599	C35—H35C	0.96

C1—N1—C8	120.20 (17)	C21—N2—C28	121.55 (17)
C1—N1—H1N	119.9	C21—N2—H2N	119.2
C8—N1—H1N	119.9	C28—N2—H2N	119.2
O1—C1—N1	121.7 (2)	O2—C21—N2	122.2 (2)
O1—C1—C2	120.00 (19)	O2—C21—C22	120.06 (19)
N1—C1—C2	118.25 (17)	N2—C21—C22	117.74 (17)
C3—C2—C7	118.9 (2)	C27—C22—C23	118.8 (2)
C3—C2—C1	117.52 (18)	C27—C22—C21	123.8 (2)
C7—C2—C1	123.5 (2)	C23—C22—C21	117.35 (17)
C4—C3—C2	121.1 (2)	C24—C23—C22	120.9 (2)
C4—C3—H3	119.4	C24—C23—H23	119.6
C2—C3—H3	119.4	C22—C23—H23	119.6
C3—C4—C5	119.8 (2)	C23—C24—C25	120.0 (2)
C3—C4—H4	120.1	C23—C24—H24	120
C5—C4—H4	120.1	C25—C24—H24	120
C6—C5—C4	119.8 (2)	C26—C25—C24	119.9 (2)
C6—C5—H5	120.1	C26—C25—H25	120
C4—C5—H5	120.1	C24—C25—H25	120
C5—C6—C7	120.9 (2)	C25—C26—C27	120.7 (2)
C5—C6—H6	119.6	C25—C26—H26	119.7
C7—C6—H6	119.6	C27—C26—H26	119.7
C2—C7—C6	119.4 (2)	C22—C27—C26	119.8 (2)
C2—C7—H7	120.3	C22—C27—H27	120.1
C6—C7—H7	120.3	C26—C27—H27	120.1
C9—C8—C13	121.9 (2)	C33—C28—C29	122.5 (3)
C9—C8—N1	119.5 (2)	C33—C28—N2	119.5 (3)
C13—C8—N1	118.6 (2)	C29—C28—N2	118.1 (3)
C10—C9—C8	118.4 (3)	C30—C29—C28	117.8 (4)
C10—C9—C15	120.3 (3)	C30—C29—C35	120.2 (4)
C8—C9—C15	121.3 (2)	C28—C29—C35	122.1 (3)
C11—C10—C9	120.6 (3)	C31—C30—C29	120.8 (4)
C11—C10—H10	119.7	C31—C30—H30	119.6
C9—C10—H10	119.7	C29—C30—H30	119.6
C12—C11—C10	120.5 (3)	C30—C31—C32	121.1 (4)
C12—C11—H11	119.8	C30—C31—H31	119.4
C10—C11—H11	119.8	C32—C31—H31	119.4
C11—C12—C13	121.5 (3)	C31—C32—C33	120.5 (4)
C11—C12—H12	119.3	C31—C32—H32	119.8
C13—C12—H12	119.3	C33—C32—H32	119.8
C12—C13—C8	117.0 (3)	C28—C33—C32	117.3 (4)
C12—C13—C14	120.6 (3)	C28—C33—C34	121.9 (3)
C8—C13—C14	122.3 (2)	C32—C33—C34	120.8 (3)
C13—C14—H14A	109.5	C33—C34—H34A	109.5
C13—C14—H14B	109.5	C33—C34—H34B	109.5
H14A—C14—H14B	109.5	H34A—C34—H34B	109.5
C13—C14—H14C	109.5	C33—C34—H34C	109.5
H14A—C14—H14C	109.5	H34A—C34—H34C	109.5
H14B—C14—H14C	109.5	H34B—C34—H34C	109.5
C9—C15—H15A	109.5	C29—C35—H35A	109.5
C9—C15—H15B	109.5	C29—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C9—C15—H15C	109.4	C29—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5

C8—N1—C1—O1	2.5 (3)	C28—N2—C21—O2	1.0 (3)
C8—N1—C1—C2	−177.4 (2)	C28—N2—C21—C22	−178.5 (2)
O1—C1—C2—C3	−16.4 (3)	O2—C21—C22—C27	−162.8 (2)
N1—C1—C2—C3	163.44 (19)	N2—C21—C22—C27	16.7 (3)
O1—C1—C2—C7	162.8 (2)	O2—C21—C22—C23	15.9 (3)
N1—C1—C2—C7	−17.3 (3)	N2—C21—C22—C23	−164.55 (19)
C7—C2—C3—C4	1.0 (3)	C27—C22—C23—C24	−0.8 (3)
C1—C2—C3—C4	−179.8 (2)	C21—C22—C23—C24	−179.6 (2)
C2—C3—C4—C5	−1.5 (4)	C22—C23—C24—C25	1.2 (4)
C3—C4—C5—C6	1.0 (4)	C23—C24—C25—C26	−0.9 (4)
C4—C5—C6—C7	0.0 (4)	C24—C25—C26—C27	0.3 (5)
C3—C2—C7—C6	0.0 (3)	C23—C22—C27—C26	0.2 (3)
C1—C2—C7—C6	−179.2 (2)	C21—C22—C27—C26	178.9 (2)
C5—C6—C7—C2	−0.5 (4)	C25—C26—C27—C22	0.1 (4)
C1—N1—C8—C9	108.7 (2)	C21—N2—C28—C33	−110.2 (3)
C1—N1—C8—C13	−69.7 (3)	C21—N2—C28—C29	68.3 (3)
C13—C8—C9—C10	2.4 (4)	C33—C28—C29—C30	−0.3 (4)
N1—C8—C9—C10	−175.9 (2)	N2—C28—C29—C30	−178.8 (3)
C13—C8—C9—C15	−178.9 (3)	C33—C28—C29—C35	−179.0 (3)
N1—C8—C9—C15	2.8 (3)	N2—C28—C29—C35	2.5 (4)
C8—C9—C10—C11	0.1 (4)	C28—C29—C30—C31	0.6 (6)
C15—C9—C10—C11	−178.7 (3)	C35—C29—C30—C31	179.4 (4)
C9—C10—C11—C12	−1.6 (6)	C29—C30—C31—C32	−0.9 (8)
C10—C11—C12—C13	0.7 (6)	C30—C31—C32—C33	0.8 (8)
C11—C12—C13—C8	1.6 (5)	C29—C28—C33—C32	0.3 (4)
C11—C12—C13—C14	−178.5 (3)	N2—C28—C33—C32	178.7 (3)
C9—C8—C13—C12	−3.2 (4)	C29—C28—C33—C34	−179.2 (3)
N1—C8—C13—C12	175.1 (2)	N2—C28—C33—C34	−0.8 (4)
C9—C8—C13—C14	176.9 (3)	C31—C32—C33—C28	−0.5 (6)
N1—C8—C13—C14	−4.8 (4)	C31—C32—C33—C34	179.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.19	2.949 (2)	147
N2—H2N···O2ⁱⁱ	0.86	2.17	2.949 (2)	150

Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO
M_r	225.28
Crystal system, space group	Monoclinic, Pc
Temperature (K)	295
a, b, c (Å)	16.4389 (8), 8.2903 (4), 9.4902 (3)
β (°)	98.165 (4)
V (Å³)	1280.25 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.52 × 0.46 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.924, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	38015, 2504, 2110
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 0.98
No. of reflections	2504
No. of parameters	307
No. of restraints	35
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14
Absolute structure	Flack (1983), 2493 Friedel pairs

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2002), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.19	2.949 (2)	147.4
N2—H2N···O2ⁱⁱ	0.86	2.17	2.949 (2)	149.8

Symmetry codes: (i) x, −y, z+1/2; (ii) x, −y+1, z+1/2.

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 the purchase of the diffractometer.

References

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