3-Methyl-N-phen­ylbenzamide

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

doi:10.1107/S1600536808008143

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o770

doi:10.1107/S1600536808008143

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3-Methyl-N-phenylbenzamide

B. Thimme Gowda,^a ^* Sabine Foro,^b B. P. Sowmya ^a 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, Darmstadt, D-64287, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 21 March 2008; accepted 26 March 2008; online 29 March 2008)

The conformation of the C=O bond in the structure of the title compound, C₁₄H₁₃NO, is anti to the meta-methyl substituent in the benzoyl ring. The conformations of the N—H and C=O bonds in the amide group are also anti to each other. The asymmetric unit of the structure contains two molecules. The bond parameters are similar to those in N-(phenyl)benzamide, 2-methyl-N-(phenyl)benzamide and other benzanilides. The amide group –NHCO– forms dihedral angles of 20.97 (34) and 45.65 (19)° with the benzoyl rings, and 41.54 (25) and 31.87 (29)° with the aniline rings, in the two independent molecules. The benzoyl and aniline rings adopt dihedral angles of 22.17 (18) and 75.86 (12)° in the two independent molecules. In the crystal structure, molecules are linked into chains by intermolecular N—H⋯O hydrogen bonds.

Related literature

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

Experimental

Crystal data

C₁₄H₁₃NO
M_r = 211.25
Monoclinic, P 2₁ /c
a = 16.947 (2) Å
b = 15.531 (1) Å
c = 8.623 (1) Å
β = 93.35 (1)°
V = 2265.7 (4) Å³
Z = 8
Cu Kα radiation
μ = 0.62 mm⁻¹
T = 299 (2) K
0.60 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD4 diffractometer
Absorption correction: none
4339 measured reflections
4039 independent reflections
2466 reflections with I > 2σ(I)
R_int = 0.034
3 standard reflections frequency: 120 min intensity decay: 1.5%

Refinement

R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.240
S = 1.03
4039 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 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	2.16	2.968 (4)	157
N2—H2N⋯O2ⁱⁱ	0.86	2.01	2.853 (3)	168
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008143/dn2328sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008143/dn2328Isup2.hkl

checkCIF report

Comment top

As part of a study of the substituent effects on the structures of benzanilides, in the present work, the structure of 3-methyl-N-(phenyl)benzamide (NP3MBA) has been determined (Gowda et al., 2003, 2008a,b).

The asymmetric unit of the structure of NP3MBA contains two molecules (Fig. 1). The conformation of the C═O bonds are anti to the meta-methyl substituents in the benzoyl phenyl rings. The conformations of the N—H and C═O bonds in the –NH—CO– groups are also anti to each other. The bond parameters in NP3MBA are similar to those in N-(phenyl)benzamide, 2-methyl-N-(phenyl)benzamide and other benzanilides (Gowda et al., 2003, 2008a,b). The amide group –NHCO– forms the dihedral angles of 20.97 (34)° (molecule 1) and 45.65(0.19) (molecule 2) with the benzoyl ring, and 41.54 (25)° (molecule 1), 31.87(0.29) (molecule 2) with the aniline ring. The benzoyl and the aniline rings have the dihedral angles of 22.17 (18)°) (molecule 1) and 75.86(0.12) (molecule 2).

The packing diagram of NP3MBA molecules showing the hydrogen bonds N1—H1N···O1, N2—H2N···O2 (Table 1) involved in the formation of molecular chain is shown in Fig. 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: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom labeling scheme. The 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.

3-Methyl-N-phenylbenzamide top

Crystal data top

C₁₄H₁₃NO	F(000) = 896
M_r = 211.25	D_x = 1.239 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 16.947 (2) Å	θ = 5.7–21.0°
b = 15.531 (1) Å	µ = 0.62 mm⁻¹
c = 8.623 (1) Å	T = 299 K
β = 93.35 (1)°	Long needle, colourless
V = 2265.7 (4) Å³	0.60 × 0.10 × 0.05 mm
Z = 8

Data collection top

Enraf–Nonius CAD4 diffractometer	R_int = 0.034
Radiation source: fine-focus sealed tube	θ_max = 66.9°, θ_min = 2.6°
Graphite monochromator	h = −20→20
ω/2θ scans	k = −1→18
4339 measured reflections	l = −10→0
4039 independent reflections	3 standard reflections every 120 min
2466 reflections with I > 2σ(I)	intensity decay: 1.5%

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.241	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.153P)²] where P = (F_o² + 2F_c²)/3
4039 reflections	(Δ/σ)_max = 0.003
291 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₄H₁₃NO	V = 2265.7 (4) Å³
M_r = 211.25	Z = 8
Monoclinic, P2₁/c	Cu Kα radiation
a = 16.947 (2) Å	µ = 0.62 mm⁻¹
b = 15.531 (1) Å	T = 299 K
c = 8.623 (1) Å	0.60 × 0.10 × 0.05 mm
β = 93.35 (1)°

Data collection top

Enraf–Nonius CAD4 diffractometer	R_int = 0.034
4339 measured reflections	3 standard reflections every 120 min
4039 independent reflections	intensity decay: 1.5%
2466 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.241	H-atom parameters constrained
S = 1.03	Δρ_max = 0.36 e Å⁻³
4039 reflections	Δρ_min = −0.39 e Å⁻³
291 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	0.24023 (18)	0.66029 (17)	0.5392 (3)	0.0558 (8)
N1	0.26569 (16)	0.75059 (19)	0.3424 (3)	0.0399 (7)
H1N	0.2562	0.7611	0.2452	0.048*
C1	0.3146 (2)	0.8100 (2)	0.4286 (3)	0.0363 (7)
C2	0.3052 (2)	0.8972 (2)	0.3996 (4)	0.0457 (9)
H2	0.2686	0.9159	0.3224	0.055*
C3	0.3502 (3)	0.9564 (3)	0.4849 (5)	0.0559 (10)
H3	0.3435	1.0150	0.4660	0.067*
C4	0.4049 (3)	0.9287 (3)	0.5978 (5)	0.0662 (12)
H4	0.4342	0.9687	0.6571	0.079*
C5	0.4163 (3)	0.8422 (3)	0.6235 (5)	0.0611 (12)
H5	0.4545	0.8237	0.6980	0.073*
C6	0.3711 (2)	0.7827 (3)	0.5385 (4)	0.0481 (9)
H6	0.3789	0.7241	0.5557	0.058*
C7	0.2328 (2)	0.6791 (2)	0.3997 (4)	0.0378 (8)
C8	0.1875 (2)	0.6216 (2)	0.2875 (4)	0.0382 (8)
C9	0.1563 (2)	0.6497 (2)	0.1438 (4)	0.0395 (8)
H9	0.1620	0.7071	0.1158	0.047*
C10	0.1167 (2)	0.5932 (3)	0.0411 (4)	0.0469 (9)
C11	0.1086 (2)	0.5083 (3)	0.0854 (5)	0.0553 (10)
H11	0.0830	0.4695	0.0173	0.066*
C12	0.1378 (3)	0.4802 (3)	0.2293 (5)	0.0598 (11)
H12	0.1308	0.4232	0.2587	0.072*
C13	0.1775 (2)	0.5369 (2)	0.3297 (5)	0.0505 (9)
H13	0.1976	0.5177	0.4263	0.061*
C14	0.0866 (3)	0.6228 (3)	−0.1174 (4)	0.0639 (12)
H14A	0.0874	0.6846	−0.1213	0.077*
H14B	0.0334	0.6027	−0.1380	0.077*
H14C	0.1197	0.6001	−0.1942	0.077*
O2	0.26730 (16)	0.32575 (17)	−0.0183 (3)	0.0498 (7)
N2	0.22500 (17)	0.24790 (19)	0.1854 (3)	0.0416 (7)
H2N	0.2375	0.2335	0.2799	0.050*
C15	0.1546 (2)	0.2116 (2)	0.1191 (4)	0.0396 (8)
C16	0.1310 (3)	0.1321 (2)	0.1709 (4)	0.0538 (10)
H16	0.1638	0.1014	0.2413	0.065*
C17	0.0593 (3)	0.0978 (3)	0.1193 (5)	0.0673 (13)
H17	0.0429	0.0453	0.1581	0.081*
C18	0.0117 (3)	0.1414 (3)	0.0100 (5)	0.0664 (12)
H18	−0.0365	0.1181	−0.0258	0.080*
C19	0.0360 (3)	0.2189 (3)	−0.0454 (5)	0.0603 (11)
H19	0.0046	0.2477	−0.1207	0.072*
C20	0.1070 (2)	0.2549 (3)	0.0098 (4)	0.0453 (9)
H20	0.1226	0.3083	−0.0268	0.054*
C21	0.2752 (2)	0.3022 (2)	0.1197 (4)	0.0386 (8)
C22	0.3426 (2)	0.3328 (2)	0.2230 (4)	0.0384 (8)
C23	0.3317 (2)	0.3609 (2)	0.3741 (4)	0.0427 (8)
H23	0.2813	0.3599	0.4114	0.051*
C24	0.3942 (2)	0.3902 (2)	0.4689 (4)	0.0458 (9)
C25	0.4691 (2)	0.3895 (2)	0.4135 (5)	0.0503 (9)
H25	0.5121	0.4079	0.4772	0.060*
C26	0.4808 (2)	0.3617 (3)	0.2633 (5)	0.0529 (10)
H26	0.5314	0.3614	0.2270	0.063*
C27	0.4178 (2)	0.3347 (2)	0.1686 (4)	0.0462 (9)
H27	0.4257	0.3176	0.0673	0.055*
C28	0.3808 (3)	0.4223 (3)	0.6316 (5)	0.0706 (14)
H28A	0.3665	0.3748	0.6955	0.085*
H28B	0.3391	0.4642	0.6270	0.085*
H28C	0.4285	0.4483	0.6753	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.095 (2)	0.0574 (16)	0.0143 (12)	−0.0142 (14)	−0.0011 (12)	0.0030 (10)
N1	0.0552 (17)	0.0488 (16)	0.0154 (12)	−0.0071 (14)	−0.0001 (12)	−0.0003 (11)
C1	0.0451 (18)	0.0481 (19)	0.0160 (14)	−0.0036 (15)	0.0039 (13)	−0.0036 (13)
C2	0.056 (2)	0.054 (2)	0.0275 (18)	−0.0009 (17)	0.0043 (16)	0.0017 (15)
C3	0.076 (3)	0.047 (2)	0.044 (2)	−0.0084 (19)	0.001 (2)	−0.0009 (17)
C4	0.087 (3)	0.065 (3)	0.045 (2)	−0.020 (2)	−0.006 (2)	−0.011 (2)
C5	0.068 (3)	0.073 (3)	0.040 (2)	−0.011 (2)	−0.016 (2)	0.002 (2)
C6	0.056 (2)	0.051 (2)	0.037 (2)	−0.0034 (17)	−0.0014 (17)	0.0017 (16)
C7	0.0488 (19)	0.0458 (19)	0.0191 (15)	0.0027 (15)	0.0043 (14)	−0.0037 (14)
C8	0.048 (2)	0.0444 (19)	0.0229 (16)	−0.0005 (15)	0.0054 (14)	−0.0051 (13)
C9	0.0483 (19)	0.0498 (19)	0.0204 (16)	−0.0092 (16)	0.0036 (14)	−0.0035 (14)
C10	0.050 (2)	0.061 (2)	0.0303 (19)	−0.0054 (17)	0.0034 (16)	−0.0093 (16)
C11	0.059 (2)	0.059 (2)	0.047 (2)	−0.011 (2)	0.0019 (19)	−0.0190 (19)
C12	0.079 (3)	0.042 (2)	0.058 (3)	−0.008 (2)	−0.005 (2)	−0.0042 (18)
C13	0.069 (3)	0.045 (2)	0.037 (2)	−0.0001 (18)	−0.0004 (18)	0.0015 (16)
C14	0.069 (3)	0.090 (3)	0.031 (2)	−0.014 (2)	−0.0042 (19)	−0.008 (2)
O2	0.0733 (18)	0.0608 (16)	0.0150 (11)	−0.0113 (13)	0.0008 (11)	0.0021 (10)
N2	0.0548 (17)	0.0534 (17)	0.0163 (13)	−0.0067 (14)	−0.0002 (12)	0.0036 (12)
C15	0.050 (2)	0.050 (2)	0.0192 (15)	−0.0040 (16)	0.0036 (14)	−0.0074 (14)
C16	0.079 (3)	0.052 (2)	0.0304 (19)	−0.008 (2)	0.0043 (18)	−0.0029 (16)
C17	0.088 (3)	0.070 (3)	0.044 (2)	−0.029 (3)	0.006 (2)	−0.008 (2)
C18	0.066 (3)	0.089 (3)	0.044 (2)	−0.021 (2)	0.003 (2)	−0.014 (2)
C19	0.062 (2)	0.081 (3)	0.037 (2)	0.004 (2)	−0.0015 (19)	−0.008 (2)
C20	0.052 (2)	0.058 (2)	0.0252 (17)	0.0003 (18)	0.0017 (15)	−0.0019 (15)
C21	0.0509 (19)	0.0455 (19)	0.0197 (15)	0.0023 (15)	0.0041 (14)	−0.0045 (13)
C22	0.050 (2)	0.0424 (19)	0.0223 (16)	−0.0011 (15)	0.0013 (14)	0.0011 (13)
C23	0.052 (2)	0.051 (2)	0.0248 (17)	−0.0048 (16)	0.0032 (15)	−0.0019 (15)
C24	0.060 (2)	0.048 (2)	0.0282 (18)	−0.0052 (17)	−0.0064 (17)	−0.0034 (15)
C25	0.054 (2)	0.053 (2)	0.043 (2)	−0.0016 (17)	−0.0085 (18)	0.0002 (17)
C26	0.047 (2)	0.060 (2)	0.052 (2)	0.0024 (18)	0.0040 (18)	0.0027 (19)
C27	0.054 (2)	0.053 (2)	0.0325 (19)	0.0030 (17)	0.0077 (16)	−0.0011 (16)
C28	0.085 (3)	0.092 (3)	0.034 (2)	−0.021 (3)	−0.002 (2)	−0.023 (2)

Geometric parameters (Å, º) top

O1—C7	1.237 (4)	O2—C21	1.244 (4)
N1—C7	1.348 (4)	N2—C21	1.347 (4)
N1—C1	1.421 (4)	N2—C15	1.409 (4)
N1—H1N	0.8600	N2—H2N	0.8600
C1—C6	1.373 (5)	C15—C20	1.379 (5)
C1—C2	1.385 (5)	C15—C16	1.382 (5)
C2—C3	1.379 (5)	C16—C17	1.376 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.373 (6)	C17—C18	1.381 (7)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.373 (6)	C18—C19	1.368 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.384 (5)	C19—C20	1.386 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.496 (5)	C21—C22	1.484 (5)
C8—C13	1.378 (5)	C22—C27	1.384 (5)
C8—C9	1.389 (5)	C22—C23	1.397 (5)
C9—C10	1.391 (5)	C23—C24	1.376 (5)
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.382 (6)	C24—C25	1.383 (6)
C10—C14	1.503 (5)	C24—C28	1.519 (5)
C11—C12	1.380 (6)	C25—C26	1.391 (6)
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.382 (5)	C26—C27	1.372 (5)
C12—H12	0.9300	C26—H26	0.9300
C13—H13	0.9300	C27—H27	0.9300
C14—H14A	0.9600	C28—H28A	0.9600
C14—H14B	0.9600	C28—H28B	0.9600
C14—H14C	0.9600	C28—H28C	0.9600

C7—N1—C1	125.7 (3)	C21—N2—C15	128.3 (3)
C7—N1—H1N	117.1	C21—N2—H2N	115.8
C1—N1—H1N	117.1	C15—N2—H2N	115.8
C6—C1—C2	119.6 (3)	C20—C15—C16	119.2 (3)
C6—C1—N1	121.5 (3)	C20—C15—N2	122.0 (3)
C2—C1—N1	118.9 (3)	C16—C15—N2	118.8 (3)
C3—C2—C1	120.2 (4)	C17—C16—C15	120.6 (4)
C3—C2—H2	119.9	C17—C16—H16	119.7
C1—C2—H2	119.9	C15—C16—H16	119.7
C4—C3—C2	119.8 (4)	C16—C17—C18	120.0 (4)
C4—C3—H3	120.1	C16—C17—H17	120.0
C2—C3—H3	120.1	C18—C17—H17	120.0
C5—C4—C3	120.3 (4)	C19—C18—C17	119.6 (4)
C5—C4—H4	119.8	C19—C18—H18	120.2
C3—C4—H4	119.8	C17—C18—H18	120.2
C4—C5—C6	119.9 (4)	C18—C19—C20	120.6 (4)
C4—C5—H5	120.0	C18—C19—H19	119.7
C6—C5—H5	120.0	C20—C19—H19	119.7
C1—C6—C5	120.1 (4)	C15—C20—C19	119.9 (4)
C1—C6—H6	120.0	C15—C20—H20	120.0
C5—C6—H6	120.0	C19—C20—H20	120.0
O1—C7—N1	122.0 (3)	O2—C21—N2	123.4 (3)
O1—C7—C8	120.4 (3)	O2—C21—C22	121.1 (3)
N1—C7—C8	117.5 (3)	N2—C21—C22	115.5 (3)
C13—C8—C9	119.3 (3)	C27—C22—C23	118.9 (3)
C13—C8—C7	117.8 (3)	C27—C22—C21	119.7 (3)
C9—C8—C7	123.0 (3)	C23—C22—C21	121.4 (3)
C8—C9—C10	121.0 (3)	C24—C23—C22	121.2 (3)
C8—C9—H9	119.5	C24—C23—H23	119.4
C10—C9—H9	119.5	C22—C23—H23	119.4
C11—C10—C9	118.5 (4)	C23—C24—C25	118.9 (3)
C11—C10—C14	120.7 (4)	C23—C24—C28	120.4 (4)
C9—C10—C14	120.8 (4)	C25—C24—C28	120.7 (4)
C12—C11—C10	121.0 (4)	C24—C25—C26	120.5 (4)
C12—C11—H11	119.5	C24—C25—H25	119.7
C10—C11—H11	119.5	C26—C25—H25	119.7
C11—C12—C13	119.9 (4)	C27—C26—C25	120.1 (4)
C11—C12—H12	120.1	C27—C26—H26	120.0
C13—C12—H12	120.1	C25—C26—H26	120.0
C8—C13—C12	120.4 (4)	C26—C27—C22	120.4 (4)
C8—C13—H13	119.8	C26—C27—H27	119.8
C12—C13—H13	119.8	C22—C27—H27	119.8
C10—C14—H14A	109.5	C24—C28—H28A	109.5
C10—C14—H14B	109.5	C24—C28—H28B	109.5
H14A—C14—H14B	109.5	H28A—C28—H28B	109.5
C10—C14—H14C	109.5	C24—C28—H28C	109.5
H14A—C14—H14C	109.5	H28A—C28—H28C	109.5
H14B—C14—H14C	109.5	H28B—C28—H28C	109.5

C7—N1—C1—C6	40.6 (5)	C21—N2—C15—C20	−32.3 (5)
C7—N1—C1—C2	−139.9 (4)	C21—N2—C15—C16	150.9 (4)
C6—C1—C2—C3	−2.6 (5)	C20—C15—C16—C17	−2.7 (6)
N1—C1—C2—C3	178.0 (3)	N2—C15—C16—C17	174.2 (4)
C1—C2—C3—C4	0.6 (6)	C15—C16—C17—C18	2.7 (7)
C2—C3—C4—C5	1.6 (7)	C16—C17—C18—C19	−0.6 (7)
C3—C4—C5—C6	−1.9 (7)	C17—C18—C19—C20	−1.5 (7)
C2—C1—C6—C5	2.3 (5)	C16—C15—C20—C19	0.7 (5)
N1—C1—C6—C5	−178.2 (4)	N2—C15—C20—C19	−176.2 (3)
C4—C5—C6—C1	−0.1 (6)	C18—C19—C20—C15	1.4 (6)
C1—N1—C7—O1	3.1 (6)	C15—N2—C21—O2	−3.5 (6)
C1—N1—C7—C8	−176.0 (3)	C15—N2—C21—C22	177.0 (3)
O1—C7—C8—C13	−21.2 (5)	O2—C21—C22—C27	−44.0 (5)
N1—C7—C8—C13	157.9 (3)	N2—C21—C22—C27	135.6 (3)
O1—C7—C8—C9	159.5 (3)	O2—C21—C22—C23	135.1 (4)
N1—C7—C8—C9	−21.4 (5)	N2—C21—C22—C23	−45.3 (5)
C13—C8—C9—C10	−1.4 (5)	C27—C22—C23—C24	−0.1 (5)
C7—C8—C9—C10	177.9 (3)	C21—C22—C23—C24	−179.2 (3)
C8—C9—C10—C11	0.4 (6)	C22—C23—C24—C25	−1.5 (6)
C8—C9—C10—C14	−176.9 (4)	C22—C23—C24—C28	178.6 (4)
C9—C10—C11—C12	1.1 (6)	C23—C24—C25—C26	1.5 (6)
C14—C10—C11—C12	178.4 (4)	C28—C24—C25—C26	−178.7 (4)
C10—C11—C12—C13	−1.6 (7)	C24—C25—C26—C27	0.1 (6)
C9—C8—C13—C12	0.9 (6)	C25—C26—C27—C22	−1.7 (6)
C7—C8—C13—C12	−178.5 (4)	C23—C22—C27—C26	1.7 (5)
C11—C12—C13—C8	0.6 (7)	C21—C22—C27—C26	−179.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.16	2.968 (4)	157
N2—H2N···O2ⁱⁱ	0.86	2.01	2.853 (3)	168

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO
M_r	211.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	299
a, b, c (Å)	16.947 (2), 15.531 (1), 8.623 (1)
β (°)	93.35 (1)
V (Å³)	2265.7 (4)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.60 × 0.10 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4339, 4039, 2466
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.241, 1.03
No. of reflections	4039
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.39

Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86	2.16	2.968 (4)	156.5
N2—H2N···O2ⁱⁱ	0.86	2.01	2.853 (3)	167.7

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Acknowledgements

BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions to his research fellowship.

References

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Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (1987). REDU4. Version 6.2c. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar