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ISSN: 2056-9890

N-(3-Methyl­phen­yl)benzamide

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 19 October 2008; accepted 28 October 2008; online 31 October 2008)

The asymmetric unit of the title compound, C14H13NO, contains four mol­ecules, which are linked through N—H⋯O hydrogen bonds into two symmetry-independent chains running parallel to [001] and [101]. The N—H and C=O bonds of the amide groups are trans oriented in all four mol­ecules. The mol­ecules are not planar and both aromatic rings are twisted strongly relative to the plane of the amide group. The dihedral angle between the two benzene rings ranges from 70.6 (2) to 74.2 (2)°. The N—H bond is anti to the meta-methyl substituent in the aniline fragment in three of the four symmetry-independent mol­ecules. In the fourth mol­ecule, the aniline unit is disordered over two nearly coplanar positions; the anti and syn conformers occupy the same site in the crystal with equal probability.

Related literature

For the general procedure for the synthesis of the title compound, see: Gowda et al. (2003[Gowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225-230.]). For structure of the 3-chloro­phenyl analogue, see: Gowda et al. (2008[Gowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o462.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13NO

  • Mr = 211.25

  • Monoclinic, C c

  • a = 13.269 (2) Å

  • b = 53.686 (6) Å

  • c = 9.3921 (12) Å

  • β = 134.21 (1)°

  • V = 4795.7 (10) Å3

  • Z = 16

  • Cu Kα radiation

  • μ = 0.58 mm−1

  • T = 299 (2) K

  • 0.43 × 0.25 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 9315 measured reflections

  • 4168 independent reflections

  • 3197 reflections with I > 2σ(I)

  • Rint = 0.028

  • 3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.129

  • S = 1.03

  • 4168 reflections

  • 653 parameters

  • 110 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯O2i 0.87 (3) 1.96 (3) 2.822 (4) 168 (4)
N2—H2N⋯O1 0.84 (3) 2.06 (3) 2.848 (4) 156 (5)
N3—H3N⋯O4ii 0.86 (3) 2.00 (3) 2.829 (4) 163 (4)
N4—H4N⋯O3i 0.82 (3) 2.04 (3) 2.813 (4) 156 (5)
Symmetry codes: (i) x-1, y, z-1; (ii) x+1, y, z.

Data collection: CAD-4-PC (Enraf–Nonius, 1996[Enraf-Nonius (1996). CAD-4-PC. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987[Stoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]) and ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the present work, the structure of N-(3-methylphenyl)-benzamide (N3MPBA) has been determined to explore the effect of substituents on the structures of benzanilides (Gowda et al., 2003, 2008). The conformations of N—H and C=O bonds in the amide group of N3MPBA are trans to each other (Fig.1 ). Further, the conformation of the N—H bond is anti to the meta-methyl substituent in the aniline fragment, similar to that observed in N-(3-chlorophenyl)-benzamide (N3CPBA). The asymmetric unit of the structure contains four molecules. Aniline fragment in one of the molecules is disordered. The amide group –NHCO– forms dihedral angles of 24.4 (9)°, 22.3 (13)°, 22.7 (16)°, 25.2 (11)° with the benzoyl fragments, in the molecules 1, 2, 3, 4, respectively, compared to the value of 18.2 (2)° in N3CPBA (Gowda et al., 2008). The dihedral angles between the two benzene rings (benzoyl and aniline fragments) in the four molecules are 70.8 (1)°, 70.6 (2)°, 73.3 (3)° and 74.2 (2)° for the molecules 1, 2, 3, 4, respectively, compared to the value of 61.0 (1)°.in N3CPBA. In the crystal structure, the molecules are linked into a chain through intermolecular N—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the general procedure for the synthesis of the title compound, see: Gowda et al. (2003). For structure of the 3-chlorophenyl analogue, see: Gowda et al. (2008).

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.

Refinement top

In the absence of significant anomalous dispersion effects, Friedel pairs were merged and the Δf" terms were set to zero.

The amide H atoms were located in difference Fourier map but in the refinement process the N—H bond lengths wereas restrained to 0.86 (3) Å. For the other H atoms idealized geometry was assumed and they were refined using a riding model with C—H = 0.93–0.96 Å. All H atoms were refined with isotropic displacement parameters (Uiso(NH) = 1.2, Uiso(CH) = 1.2 and Uiso(CH3) = 1.5 Ueq of the parent atom).

The benzene ring C29—C34 and the methyl group C42 are disordered over two nearly co-planar positions. The corresponding bond distances in the disordered groups were restrained to be equal. The site-occupancy factors were initially refined for the two positions of the methylphenyl fragment but they converged close to 0.5 and therefore the occupancy of the two positions was assumed to be equal 0.5. The Uij values of the disordered atoms and those of C45 and C46 were restrained by ISOR instruction to approximate isotropic behaviour

Computing details top

Data collection: CAD-4-PC (Enraf–Nonius, 1996); cell refinement: CAD-4-PC (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) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level. Both disordered components are shown (the bonds of the second component are drawn with dashed lines).
[Figure 2] Fig. 2. The molecular packing of the title compound, with hydrogen bonds shown as dashed lines. For clarity, the disordered components and the H atoms not involved in hydrogen bonding have been omitted.
N-(3-Methylphenyl)benzamide top
Crystal data top
C14H13NOF(000) = 1792
Mr = 211.25Dx = 1.170 Mg m3
Monoclinic, CcCu Kα radiation, λ = 1.54180 Å
Hall symbol: C -2ycCell parameters from 25 reflections
a = 13.269 (2) Åθ = 3.3–20.6°
b = 53.686 (6) ŵ = 0.58 mm1
c = 9.3921 (12) ÅT = 299 K
β = 134.21 (1)°Prism, colourless
V = 4795.7 (10) Å30.43 × 0.25 × 0.10 mm
Z = 16
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.028
Radiation source: fine-focus sealed tubeθmax = 67.0°, θmin = 1.7°
Graphite monochromatorh = 1115
ω/2θ scansk = 6464
9315 measured reflectionsl = 101
4168 independent reflections3 standard reflections every 120 min
3197 reflections with I > 2σ(I) intensity decay: 1.0%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0731P)2 + 0.8953P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.017
4168 reflectionsΔρmax = 0.27 e Å3
653 parametersΔρmin = 0.13 e Å3
110 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00065 (10)
Crystal data top
C14H13NOV = 4795.7 (10) Å3
Mr = 211.25Z = 16
Monoclinic, CcCu Kα radiation
a = 13.269 (2) ŵ = 0.58 mm1
b = 53.686 (6) ÅT = 299 K
c = 9.3921 (12) Å0.43 × 0.25 × 0.10 mm
β = 134.21 (1)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.028
9315 measured reflections3 standard reflections every 120 min
4168 independent reflections intensity decay: 1.0%
3197 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.044110 restraints
wR(F2) = 0.129H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.27 e Å3
4168 reflectionsΔρmin = 0.13 e Å3
653 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
xyzUiso*/UeqOcc. (<1)
C10.0268 (4)0.07396 (7)0.1918 (5)0.0628 (9)
C20.1291 (5)0.09159 (8)0.2900 (7)0.0769 (11)
H20.16900.09620.24280.092*
C30.1760 (5)0.10310 (10)0.4642 (8)0.0960 (15)
C40.1127 (6)0.09577 (11)0.5244 (8)0.1005 (16)
H40.14160.10300.63810.121*
C50.0110 (7)0.07874 (11)0.4278 (8)0.1040 (16)
H50.03010.07450.47380.125*
C60.0333 (5)0.06749 (9)0.2617 (6)0.0814 (12)
H60.10370.05550.19560.098*
C70.0673 (3)0.05123 (7)0.0101 (5)0.0549 (8)
C80.0021 (3)0.03782 (6)0.1759 (5)0.0526 (8)
C90.0812 (4)0.01993 (7)0.1675 (6)0.0673 (10)
H90.17290.01690.04740.081*
C100.0272 (4)0.00661 (8)0.3325 (7)0.0814 (12)
H100.08140.00570.32250.098*
C110.1061 (4)0.01127 (8)0.5119 (6)0.0801 (12)
H110.14180.00250.62430.096*
C120.1859 (4)0.02881 (9)0.5248 (6)0.0800 (12)
H120.27670.03190.64650.096*
C130.1334 (4)0.04215 (7)0.3580 (5)0.0663 (10)
H130.18940.05400.36860.080*
C140.2931 (8)0.12100 (15)0.5724 (11)0.155 (3)
H14A0.26860.13440.48530.232*
H14B0.37570.11270.61860.232*
H14C0.31140.12750.68380.232*
O10.1948 (3)0.05155 (6)0.1495 (4)0.0849 (9)
N10.0196 (3)0.06211 (6)0.0193 (4)0.0606 (7)
H1N0.109 (3)0.0583 (7)0.064 (6)0.073*
C150.5271 (4)0.07424 (7)0.4130 (7)0.0704 (10)
C160.6297 (5)0.09202 (8)0.5177 (8)0.0877 (13)
H160.66870.09720.64190.105*
C170.6765 (5)0.10269 (9)0.4285 (10)0.0962 (16)
C180.6156 (7)0.09404 (11)0.2474 (11)0.1102 (17)
H180.64820.10030.19330.132*
C190.5128 (7)0.07729 (12)0.1419 (10)0.1151 (18)
H190.47230.07260.01590.138*
C200.4667 (5)0.06676 (10)0.2261 (7)0.0877 (13)
H200.39590.05480.15630.105*
C210.5657 (3)0.05192 (7)0.6757 (5)0.0630 (9)
C220.5001 (3)0.03832 (7)0.7316 (5)0.0574 (8)
C230.5806 (4)0.02076 (8)0.8826 (6)0.0751 (11)
H230.67300.01800.94540.090*
C240.5267 (5)0.00746 (9)0.9406 (7)0.0837 (12)
H240.58180.00441.04020.100*
C250.3922 (5)0.01154 (9)0.8532 (7)0.0870 (13)
H250.35580.00260.89370.104*
C260.3107 (4)0.02906 (9)0.7047 (7)0.0843 (13)
H260.21940.03200.64600.101*
C270.3634 (4)0.04224 (8)0.6425 (6)0.0695 (10)
H270.30690.05380.54040.083*
C280.7952 (8)0.12088 (14)0.5522 (13)0.151 (3)
H28A0.76790.13610.47940.227*
H28B0.87580.11400.58430.227*
H28C0.81810.12420.67250.227*
O20.6934 (2)0.05281 (7)0.7906 (4)0.0939 (10)
N20.4806 (3)0.06267 (6)0.4954 (5)0.0649 (8)
H2N0.395 (3)0.0596 (7)0.418 (6)0.078*
C29A0.8798 (11)0.1769 (2)0.9070 (18)0.056 (3)0.50
C30A0.7568 (10)0.18485 (19)0.7249 (15)0.070 (3)0.50
H30A0.75660.19760.65770.084*0.50
C31A0.6348 (10)0.1735 (2)0.6450 (17)0.084 (3)0.50
H31A0.55070.17840.52020.101*0.50
C32A0.6326 (13)0.1549 (3)0.744 (2)0.091 (4)0.50
H32A0.54720.14770.68530.110*0.50
C33A0.7536 (17)0.1469 (3)0.928 (3)0.090 (4)0.50
C34A0.8778 (10)0.15780 (17)1.0046 (14)0.066 (2)0.50
H34A0.96250.15221.12550.079*0.50
C29B0.9176 (10)0.1711 (2)0.9772 (16)0.061 (3)0.50
C30B0.9455 (11)0.15245 (18)1.0998 (16)0.076 (2)0.50
H30B1.03760.14901.21760.091*0.50
C31B0.8368 (13)0.1389 (2)1.047 (2)0.103 (3)0.50
H31B0.85270.12651.13050.124*0.50
C32B0.7039 (18)0.1440 (3)0.869 (3)0.100 (5)0.50
H32B0.63120.13410.83210.120*0.50
C33B0.6700 (13)0.1622 (3)0.744 (2)0.084 (3)0.50
C34B0.7839 (13)0.1759 (2)0.8012 (19)0.072 (3)0.50
H34B0.76790.18840.71850.087*0.50
C351.1118 (4)0.19803 (7)1.1899 (5)0.0628 (9)
C361.2296 (4)0.21224 (6)1.2413 (5)0.0563 (8)
C371.2951 (4)0.22996 (8)1.3885 (6)0.0747 (11)
H371.26380.23281.45010.090*
C381.4067 (5)0.24351 (9)1.4454 (7)0.0876 (13)
H381.45070.25541.54540.105*
C391.4528 (5)0.23942 (9)1.3541 (7)0.0830 (12)
H391.52780.24851.39180.100*
C401.3880 (5)0.22196 (9)1.2081 (7)0.0805 (12)
H401.42040.21901.14820.097*
C411.2753 (4)0.20854 (7)1.1477 (6)0.0664 (10)
H411.23000.19711.04480.080*
C42A0.7536 (14)0.1263 (2)1.037 (2)0.128 (4)0.50
H42A0.78810.13271.15970.153*0.50
H42B0.81310.11301.06350.153*0.50
H42C0.65960.12020.95650.153*0.50
C42B0.5236 (13)0.1672 (2)0.5592 (18)0.124 (4)0.50
H42D0.47250.17290.59070.149*0.50
H42E0.48120.15220.48170.149*0.50
H42F0.52140.17980.48450.149*0.50
O31.0999 (4)0.19713 (7)1.3092 (5)0.0986 (11)
N31.0189 (4)0.18720 (6)1.0112 (5)0.0688 (8)
H3N1.008 (5)0.1884 (8)0.910 (5)0.083*
C430.1504 (4)0.17535 (7)0.6956 (6)0.0675 (10)
C440.1398 (6)0.15736 (8)0.7880 (7)0.0833 (12)
H440.05210.15270.73650.100*
C450.2631 (7)0.14582 (10)0.9623 (8)0.1007 (17)
C460.3895 (7)0.15302 (12)1.0333 (9)0.1094 (18)
H460.47090.14571.14930.131*
C470.4011 (6)0.17042 (12)0.9410 (9)0.1085 (18)
H470.48870.17470.99050.130*
C480.2805 (5)0.18180 (10)0.7720 (7)0.0887 (13)
H480.28760.19400.70910.106*
C490.0664 (4)0.19878 (7)0.5125 (5)0.0623 (9)
C500.1861 (4)0.21174 (7)0.3245 (5)0.0564 (8)
C510.2317 (4)0.20666 (8)0.1450 (6)0.0739 (11)
H510.18600.19460.13580.089*
C520.3455 (5)0.21933 (10)0.0237 (6)0.0897 (14)
H520.37670.21550.14570.108*
C530.4119 (5)0.23724 (9)0.0131 (7)0.0860 (13)
H530.48820.24570.12700.103*
C540.3655 (5)0.24283 (9)0.1677 (7)0.0828 (12)
H540.40920.25530.17700.099*
C550.2547 (4)0.22996 (8)0.3339 (6)0.0706 (10)
H550.22520.23350.45510.085*
C560.2485 (9)0.12685 (13)1.0643 (11)0.147 (3)
H56A0.19410.11300.97670.221*
H56B0.20210.13431.09880.221*
H56C0.34010.12111.18260.221*
O40.0545 (3)0.19914 (7)0.6551 (4)0.0918 (9)
N40.0282 (3)0.18719 (6)0.5235 (5)0.0661 (8)
H4N0.026 (5)0.1923 (8)0.439 (6)0.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0554 (19)0.060 (2)0.0539 (19)0.0061 (16)0.0311 (17)0.0023 (16)
C20.076 (3)0.071 (2)0.078 (3)0.005 (2)0.052 (2)0.010 (2)
C30.087 (3)0.079 (3)0.089 (3)0.010 (2)0.050 (3)0.020 (2)
C40.116 (4)0.110 (4)0.084 (3)0.006 (3)0.073 (3)0.017 (3)
C50.115 (4)0.122 (4)0.091 (3)0.004 (4)0.078 (3)0.017 (3)
C60.086 (3)0.099 (3)0.073 (3)0.007 (2)0.061 (2)0.013 (2)
C70.0422 (17)0.066 (2)0.0504 (18)0.0015 (14)0.0302 (16)0.0017 (15)
C80.0417 (15)0.0613 (18)0.0519 (18)0.0001 (14)0.0316 (14)0.0067 (15)
C90.0509 (18)0.079 (2)0.063 (2)0.0065 (17)0.0369 (18)0.0004 (19)
C100.067 (2)0.088 (3)0.090 (3)0.002 (2)0.055 (2)0.016 (2)
C110.071 (2)0.093 (3)0.071 (3)0.013 (2)0.048 (2)0.026 (2)
C120.059 (2)0.098 (3)0.055 (2)0.001 (2)0.0288 (18)0.012 (2)
C130.0500 (18)0.074 (2)0.058 (2)0.0077 (16)0.0314 (17)0.0004 (18)
C140.156 (6)0.148 (6)0.150 (7)0.074 (5)0.103 (6)0.075 (5)
O10.0409 (13)0.134 (3)0.0570 (15)0.0001 (14)0.0259 (12)0.0183 (16)
N10.0432 (13)0.0758 (19)0.0517 (15)0.0011 (13)0.0290 (12)0.0077 (14)
C150.0543 (19)0.066 (2)0.084 (3)0.0085 (17)0.046 (2)0.011 (2)
C160.066 (2)0.074 (3)0.113 (4)0.005 (2)0.058 (3)0.009 (3)
C170.083 (3)0.069 (3)0.140 (5)0.000 (2)0.079 (3)0.002 (3)
C180.122 (5)0.105 (4)0.125 (5)0.002 (4)0.094 (4)0.004 (4)
C190.126 (5)0.110 (4)0.120 (5)0.004 (4)0.090 (4)0.003 (4)
C200.087 (3)0.099 (3)0.087 (3)0.000 (2)0.064 (3)0.008 (3)
C210.0408 (18)0.076 (2)0.0552 (19)0.0005 (16)0.0271 (16)0.0074 (18)
C220.0439 (15)0.070 (2)0.0473 (17)0.0005 (15)0.0278 (15)0.0066 (16)
C230.0524 (19)0.089 (3)0.063 (2)0.0095 (19)0.0322 (18)0.004 (2)
C240.069 (2)0.092 (3)0.068 (2)0.002 (2)0.040 (2)0.014 (2)
C250.073 (2)0.094 (3)0.078 (3)0.009 (2)0.046 (2)0.004 (2)
C260.058 (2)0.109 (3)0.088 (3)0.003 (2)0.051 (2)0.015 (3)
C270.0481 (18)0.080 (2)0.065 (2)0.0057 (17)0.0341 (18)0.0065 (19)
C280.150 (6)0.127 (5)0.203 (8)0.053 (5)0.132 (6)0.033 (5)
O20.0388 (14)0.156 (3)0.0672 (17)0.0020 (15)0.0299 (13)0.0121 (18)
N20.0403 (13)0.081 (2)0.0593 (18)0.0014 (14)0.0295 (14)0.0028 (15)
C29A0.064 (6)0.057 (5)0.061 (6)0.002 (5)0.048 (5)0.006 (5)
C30A0.066 (5)0.067 (5)0.067 (5)0.002 (4)0.042 (4)0.011 (4)
C31A0.060 (5)0.096 (6)0.084 (5)0.006 (4)0.045 (4)0.017 (5)
C32A0.078 (6)0.088 (7)0.102 (7)0.014 (5)0.060 (6)0.018 (6)
C33A0.089 (8)0.090 (7)0.091 (8)0.002 (6)0.062 (6)0.016 (6)
C34A0.067 (5)0.059 (4)0.062 (5)0.001 (4)0.041 (4)0.012 (4)
C29B0.060 (5)0.065 (6)0.062 (6)0.002 (5)0.044 (5)0.007 (5)
C30B0.076 (5)0.078 (5)0.079 (6)0.006 (4)0.056 (5)0.014 (5)
C31B0.107 (7)0.095 (6)0.107 (7)0.011 (5)0.075 (6)0.002 (5)
C32B0.094 (8)0.092 (8)0.107 (9)0.015 (6)0.067 (7)0.005 (7)
C33B0.080 (6)0.077 (7)0.087 (6)0.009 (5)0.056 (5)0.005 (5)
C34B0.077 (6)0.071 (6)0.069 (6)0.003 (5)0.051 (5)0.001 (5)
C350.069 (2)0.073 (2)0.059 (2)0.0066 (18)0.049 (2)0.0058 (18)
C360.0578 (18)0.066 (2)0.0483 (17)0.0068 (16)0.0382 (16)0.0051 (16)
C370.087 (3)0.089 (3)0.063 (2)0.004 (2)0.057 (2)0.013 (2)
C380.098 (3)0.096 (3)0.071 (3)0.027 (3)0.060 (3)0.024 (2)
C390.084 (3)0.092 (3)0.074 (3)0.027 (2)0.056 (2)0.009 (2)
C400.087 (3)0.095 (3)0.086 (3)0.015 (2)0.070 (3)0.009 (2)
C410.076 (2)0.071 (2)0.069 (2)0.0065 (18)0.056 (2)0.0071 (18)
C42A0.121 (7)0.127 (8)0.148 (8)0.017 (6)0.099 (6)0.040 (6)
C42B0.103 (7)0.129 (7)0.105 (7)0.012 (6)0.059 (5)0.007 (6)
O30.102 (2)0.154 (3)0.0793 (18)0.024 (2)0.0777 (19)0.0162 (19)
N30.0747 (19)0.082 (2)0.069 (2)0.0147 (16)0.0574 (18)0.0115 (17)
C430.080 (3)0.070 (2)0.058 (2)0.0092 (19)0.050 (2)0.0008 (18)
C440.106 (3)0.071 (3)0.075 (3)0.013 (2)0.064 (3)0.001 (2)
C450.142 (5)0.078 (3)0.085 (3)0.027 (3)0.081 (3)0.015 (2)
C460.100 (4)0.118 (4)0.090 (4)0.035 (3)0.059 (3)0.009 (3)
C470.090 (3)0.129 (5)0.086 (3)0.029 (3)0.054 (3)0.007 (3)
C480.080 (3)0.102 (3)0.083 (3)0.018 (2)0.056 (3)0.003 (3)
C490.067 (2)0.076 (2)0.056 (2)0.0033 (18)0.0470 (19)0.0041 (17)
C500.0577 (18)0.066 (2)0.0540 (19)0.0034 (15)0.0419 (17)0.0022 (16)
C510.085 (3)0.085 (3)0.061 (2)0.012 (2)0.054 (2)0.001 (2)
C520.094 (3)0.117 (4)0.059 (2)0.021 (3)0.054 (2)0.008 (2)
C530.083 (3)0.109 (3)0.070 (3)0.022 (2)0.055 (2)0.028 (2)
C540.085 (3)0.091 (3)0.091 (3)0.017 (2)0.068 (3)0.012 (3)
C550.072 (2)0.085 (3)0.064 (2)0.005 (2)0.051 (2)0.000 (2)
C560.187 (7)0.116 (5)0.132 (6)0.036 (5)0.109 (6)0.049 (4)
O40.090 (2)0.141 (3)0.0584 (16)0.0276 (19)0.0568 (16)0.0143 (17)
N40.0693 (18)0.081 (2)0.0593 (18)0.0106 (16)0.0490 (16)0.0079 (15)
Geometric parameters (Å, º) top
C1—C21.357 (6)C32A—H32A0.9300
C1—C61.385 (6)C33A—C34A1.386 (17)
C1—N11.420 (5)C33A—C42A1.503 (16)
C2—C31.423 (7)C34A—H34A0.9300
C2—H20.9300C29B—C34B1.362 (13)
C3—C41.359 (8)C29B—C30B1.367 (13)
C3—C141.472 (8)C29B—N31.435 (11)
C4—C51.331 (8)C30B—C31B1.365 (13)
C4—H40.9300C30B—H30B0.9300
C5—C61.366 (7)C31B—C32B1.367 (16)
C5—H50.9300C31B—H31B0.9300
C6—H60.9300C32B—C33B1.344 (16)
C7—O11.219 (4)C32B—H32B0.9300
C7—N11.348 (4)C33B—C34B1.407 (16)
C7—C81.487 (5)C33B—C42B1.468 (16)
C8—C91.384 (5)C34B—H34B0.9300
C8—C131.387 (5)C35—O31.236 (5)
C9—C101.371 (6)C35—N31.338 (5)
C9—H90.9300C35—C361.486 (5)
C10—C111.369 (6)C36—C371.377 (5)
C10—H100.9300C36—C411.386 (5)
C11—C121.358 (6)C37—C381.380 (6)
C11—H110.9300C37—H370.9300
C12—C131.389 (6)C38—C391.374 (7)
C12—H120.9300C38—H380.9300
C13—H130.9300C39—C401.362 (6)
C14—H14A0.9600C39—H390.9300
C14—H14B0.9600C40—C411.376 (6)
C14—H14C0.9600C40—H400.9300
N1—H1N0.87 (3)C41—H410.9300
C15—C161.366 (6)C42A—H42A0.9600
C15—C201.387 (6)C42A—H42B0.9600
C15—N21.426 (5)C42A—H42C0.9600
C16—C171.463 (8)C42B—H42D0.9600
C16—H160.9300C42B—H42E0.9600
C17—C181.359 (8)C42B—H42F0.9600
C17—C281.494 (8)N3—H3N0.86 (3)
C18—C191.329 (8)C43—C441.370 (6)
C18—H180.9300C43—C481.373 (7)
C19—C201.413 (8)C43—N41.411 (5)
C19—H190.9300C44—C451.416 (7)
C20—H200.9300C44—H440.9300
C21—O21.219 (4)C45—C461.360 (9)
C21—N21.345 (5)C45—C561.500 (9)
C21—C221.484 (5)C46—C471.353 (9)
C22—C271.385 (5)C46—H460.9300
C22—C231.389 (5)C47—C481.382 (7)
C23—C241.364 (6)C47—H470.9300
C23—H230.9300C48—H480.9300
C24—C251.365 (6)C49—O41.234 (4)
C24—H240.9300C49—N41.339 (5)
C25—C261.377 (6)C49—C501.488 (5)
C25—H250.9300C50—C511.365 (5)
C26—C271.378 (6)C50—C551.380 (5)
C26—H260.9300C51—C521.384 (6)
C27—H270.9300C51—H510.9300
C28—H28A0.9600C52—C531.354 (7)
C28—H28B0.9600C52—H520.9300
C28—H28C0.9600C53—C541.376 (7)
N2—H2N0.84 (3)C53—H530.9300
C29A—C30A1.371 (13)C54—C551.369 (6)
C29A—C34A1.386 (12)C54—H540.9300
C29A—N31.467 (10)C55—H550.9300
C30A—C31A1.365 (12)C56—H56A0.9600
C30A—H30A0.9300C56—H56B0.9600
C31A—C32A1.379 (14)C56—H56C0.9600
C31A—H31A0.9300N4—H4N0.82 (3)
C32A—C33A1.371 (15)
C2—C1—C6119.0 (4)C32A—C33A—C42A122.1 (13)
C2—C1—N1121.4 (4)C34A—C33A—C42A121.4 (13)
C6—C1—N1119.6 (4)C33A—C34A—C29A122.2 (10)
C1—C2—C3120.9 (5)C33A—C34A—H34A118.9
C1—C2—H2119.6C29A—C34A—H34A118.9
C3—C2—H2119.6C34B—C29B—C30B121.3 (10)
C4—C3—C2116.8 (5)C34B—C29B—N3112.4 (9)
C4—C3—C14124.3 (6)C30B—C29B—N3126.3 (8)
C2—C3—C14118.8 (6)C31B—C30B—C29B119.3 (11)
C5—C4—C3122.9 (5)C31B—C30B—H30B120.3
C5—C4—H4118.6C29B—C30B—H30B120.3
C3—C4—H4118.6C30B—C31B—C32B118.0 (13)
C4—C5—C6120.4 (6)C30B—C31B—H31B121.0
C4—C5—H5119.8C32B—C31B—H31B121.0
C6—C5—H5119.8C33B—C32B—C31B125.2 (16)
C5—C6—C1120.0 (5)C33B—C32B—H32B117.4
C5—C6—H6120.0C31B—C32B—H32B117.4
C1—C6—H6120.0C32B—C33B—C34B115.5 (13)
O1—C7—N1122.2 (3)C32B—C33B—C42B121.8 (14)
O1—C7—C8120.3 (3)C34B—C33B—C42B122.6 (13)
N1—C7—C8117.5 (3)C29B—C34B—C33B120.5 (11)
C9—C8—C13117.8 (3)C29B—C34B—H34B119.8
C9—C8—C7118.2 (3)C33B—C34B—H34B119.8
C13—C8—C7124.0 (3)O3—C35—N3122.1 (4)
C10—C9—C8121.4 (3)O3—C35—C36119.8 (4)
C10—C9—H9119.3N3—C35—C36118.1 (3)
C8—C9—H9119.3C37—C36—C41119.2 (4)
C11—C10—C9120.3 (4)C37—C36—C35117.7 (3)
C11—C10—H10119.9C41—C36—C35123.1 (3)
C9—C10—H10119.9C36—C37—C38120.5 (4)
C12—C11—C10119.7 (4)C36—C37—H37119.7
C12—C11—H11120.2C38—C37—H37119.7
C10—C11—H11120.2C39—C38—C37119.9 (4)
C11—C12—C13120.7 (4)C39—C38—H38120.0
C11—C12—H12119.7C37—C38—H38120.0
C13—C12—H12119.7C40—C39—C38119.7 (4)
C8—C13—C12120.2 (4)C40—C39—H39120.2
C8—C13—H13119.9C38—C39—H39120.2
C12—C13—H13119.9C39—C40—C41121.1 (4)
C3—C14—H14A109.5C39—C40—H40119.4
C3—C14—H14B109.5C41—C40—H40119.4
H14A—C14—H14B109.5C40—C41—C36119.6 (4)
C3—C14—H14C109.5C40—C41—H41120.2
H14A—C14—H14C109.5C36—C41—H41120.2
H14B—C14—H14C109.5C33A—C42A—H42A109.5
C7—N1—C1123.9 (3)C33A—C42A—H42B109.5
C7—N1—H1N121 (3)H42A—C42A—H42B109.5
C1—N1—H1N112 (3)C33A—C42A—H42C109.5
C16—C15—C20121.3 (5)H42A—C42A—H42C109.5
C16—C15—N2120.3 (4)H42B—C42A—H42C109.5
C20—C15—N2118.3 (4)C33B—C42B—H42D109.5
C15—C16—C17118.0 (5)C33B—C42B—H42E109.5
C15—C16—H16121.0H42D—C42B—H42E109.5
C17—C16—H16121.0C33B—C42B—H42F109.5
C18—C17—C16117.6 (5)H42D—C42B—H42F109.5
C18—C17—C28125.5 (6)H42E—C42B—H42F109.5
C16—C17—C28116.7 (6)C35—N3—C29B116.2 (6)
C19—C18—C17124.7 (6)C35—N3—C29A129.2 (6)
C19—C18—H18117.6C35—N3—H3N131 (3)
C17—C18—H18117.6C29B—N3—H3N113 (3)
C18—C19—C20118.3 (6)C29A—N3—H3N97 (3)
C18—C19—H19120.9C44—C43—C48119.6 (4)
C20—C19—H19120.9C44—C43—N4120.0 (4)
C15—C20—C19120.0 (5)C48—C43—N4120.4 (4)
C15—C20—H20120.0C43—C44—C45119.6 (5)
C19—C20—H20120.0C43—C44—H44120.2
O2—C21—N2121.7 (4)C45—C44—H44120.2
O2—C21—C22120.1 (3)C46—C45—C44118.6 (5)
N2—C21—C22118.1 (3)C46—C45—C56123.0 (6)
C27—C22—C23118.1 (4)C44—C45—C56118.4 (6)
C27—C22—C21123.8 (3)C47—C46—C45122.3 (6)
C23—C22—C21118.2 (3)C47—C46—H46118.9
C24—C23—C22121.3 (4)C45—C46—H46118.9
C24—C23—H23119.4C46—C47—C48118.9 (6)
C22—C23—H23119.4C46—C47—H47120.6
C23—C24—C25120.4 (4)C48—C47—H47120.6
C23—C24—H24119.8C43—C48—C47121.0 (6)
C25—C24—H24119.8C43—C48—H48119.5
C24—C25—C26119.5 (5)C47—C48—H48119.5
C24—C25—H25120.3O4—C49—N4121.3 (3)
C26—C25—H25120.3O4—C49—C50120.2 (3)
C25—C26—C27120.5 (4)N4—C49—C50118.5 (3)
C25—C26—H26119.7C51—C50—C55118.5 (4)
C27—C26—H26119.7C51—C50—C49124.0 (3)
C26—C27—C22120.2 (4)C55—C50—C49117.5 (3)
C26—C27—H27119.9C50—C51—C52120.4 (4)
C22—C27—H27119.9C50—C51—H51119.8
C17—C28—H28A109.5C52—C51—H51119.8
C17—C28—H28B109.5C53—C52—C51120.7 (4)
H28A—C28—H28B109.5C53—C52—H52119.6
C17—C28—H28C109.5C51—C52—H52119.6
H28A—C28—H28C109.5C52—C53—C54119.4 (4)
H28B—C28—H28C109.5C52—C53—H53120.3
C21—N2—C15124.7 (3)C54—C53—H53120.3
C21—N2—H2N116 (3)C55—C54—C53119.8 (4)
C15—N2—H2N117 (3)C55—C54—H54120.1
C30A—C29A—C34A120.1 (9)C53—C54—H54120.1
C30A—C29A—N3124.2 (8)C54—C55—C50121.1 (4)
C34A—C29A—N3115.7 (9)C54—C55—H55119.5
C31A—C30A—C29A118.0 (10)C50—C55—H55119.5
C31A—C30A—H30A121.0C45—C56—H56A109.5
C29A—C30A—H30A121.0C45—C56—H56B109.5
C30A—C31A—C32A121.9 (11)H56A—C56—H56B109.5
C30A—C31A—H31A119.1C45—C56—H56C109.5
C32A—C31A—H31A119.1H56A—C56—H56C109.5
C33A—C32A—C31A121.3 (12)H56B—C56—H56C109.5
C33A—C32A—H32A119.3C49—N4—C43124.4 (3)
C31A—C32A—H32A119.3C49—N4—H4N112 (3)
C32A—C33A—C34A116.5 (11)C43—N4—H4N120 (3)
C6—C1—C2—C30.9 (6)N3—C29A—C34A—C33A177.5 (13)
N1—C1—C2—C3179.1 (4)C34B—C29B—C30B—C31B2.0 (19)
C1—C2—C3—C40.7 (7)N3—C29B—C30B—C31B179.2 (11)
C1—C2—C3—C14176.3 (6)C29B—C30B—C31B—C32B2 (2)
C2—C3—C4—C50.2 (8)C30B—C31B—C32B—C33B3 (3)
C14—C3—C4—C5177.0 (7)C31B—C32B—C33B—C34B3 (3)
C3—C4—C5—C60.8 (9)C31B—C32B—C33B—C42B177.0 (17)
C4—C5—C6—C10.6 (8)C30B—C29B—C34B—C33B2 (2)
C2—C1—C6—C50.3 (7)N3—C29B—C34B—C33B179.1 (10)
N1—C1—C6—C5179.8 (4)C32B—C33B—C34B—C29B2 (2)
O1—C7—C8—C919.4 (5)C42B—C33B—C34B—C29B177.6 (13)
N1—C7—C8—C9158.6 (3)O3—C35—C36—C3719.7 (5)
O1—C7—C8—C13160.5 (4)N3—C35—C36—C37158.2 (4)
N1—C7—C8—C1321.6 (5)O3—C35—C36—C41160.7 (4)
C13—C8—C9—C101.0 (6)N3—C35—C36—C4121.5 (5)
C7—C8—C9—C10179.1 (4)C41—C36—C37—C381.4 (6)
C8—C9—C10—C111.8 (7)C35—C36—C37—C38178.9 (4)
C9—C10—C11—C121.5 (7)C36—C37—C38—C390.3 (7)
C10—C11—C12—C130.3 (7)C37—C38—C39—C400.1 (7)
C9—C8—C13—C120.1 (6)C38—C39—C40—C411.1 (7)
C7—C8—C13—C12179.7 (4)C39—C40—C41—C362.1 (7)
C11—C12—C13—C80.5 (7)C37—C36—C41—C402.3 (6)
O1—C7—N1—C12.7 (6)C35—C36—C41—C40178.1 (4)
C8—C7—N1—C1175.2 (3)O3—C35—N3—C29B9.9 (8)
C2—C1—N1—C751.7 (5)C36—C35—N3—C29B172.3 (6)
C6—C1—N1—C7128.3 (4)O3—C35—N3—C29A12.1 (9)
C20—C15—C16—C171.2 (6)C36—C35—N3—C29A165.7 (6)
N2—C15—C16—C17178.1 (4)C34B—C29B—N3—C35131.8 (9)
C15—C16—C17—C180.6 (7)C30B—C29B—N3—C3549.3 (14)
C15—C16—C17—C28176.2 (5)C34B—C29B—N3—C29A1.2 (18)
C16—C17—C18—C192.7 (9)C30A—C29A—N3—C35120.8 (12)
C28—C17—C18—C19177.9 (7)C34A—C29A—N3—C3559.3 (13)
C17—C18—C19—C202.9 (10)C30A—C29A—N3—C29B178 (4)
C16—C15—C20—C191.0 (7)C34A—C29A—N3—C29B2.2 (18)
N2—C15—C20—C19178.2 (4)C48—C43—C44—C450.7 (6)
C18—C19—C20—C150.9 (8)N4—C43—C44—C45179.1 (4)
O2—C21—C22—C27160.0 (4)C43—C44—C45—C460.0 (7)
N2—C21—C22—C2721.1 (5)C43—C44—C45—C56177.8 (5)
O2—C21—C22—C2319.6 (5)C44—C45—C46—C471.3 (9)
N2—C21—C22—C23159.3 (4)C56—C45—C46—C47179.0 (6)
C27—C22—C23—C240.8 (6)C45—C46—C47—C482.0 (9)
C21—C22—C23—C24179.6 (4)C44—C43—C48—C470.0 (7)
C22—C23—C24—C251.3 (7)N4—C43—C48—C47179.7 (4)
C23—C24—C25—C260.5 (7)C46—C47—C48—C431.2 (8)
C24—C25—C26—C270.8 (8)O4—C49—C50—C51160.1 (4)
C25—C26—C27—C221.2 (7)N4—C49—C50—C5121.0 (6)
C23—C22—C27—C260.5 (6)O4—C49—C50—C5519.7 (5)
C21—C22—C27—C26179.1 (4)N4—C49—C50—C55159.2 (4)
O2—C21—N2—C155.2 (6)C55—C50—C51—C520.9 (6)
C22—C21—N2—C15173.6 (3)C49—C50—C51—C52179.0 (4)
C16—C15—N2—C2152.2 (5)C50—C51—C52—C531.2 (8)
C20—C15—N2—C21127.1 (4)C51—C52—C53—C540.1 (8)
C34A—C29A—C30A—C31A0.0 (19)C52—C53—C54—C551.2 (7)
N3—C29A—C30A—C31A179.9 (10)C53—C54—C55—C501.5 (7)
C29A—C30A—C31A—C32A1.5 (19)C51—C50—C55—C540.4 (6)
C30A—C31A—C32A—C33A0 (2)C49—C50—C55—C54179.7 (4)
C31A—C32A—C33A—C34A2 (3)O4—C49—N4—C432.4 (6)
C31A—C32A—C33A—C42A179.0 (16)C50—C49—N4—C43176.5 (4)
C32A—C33A—C34A—C29A3 (3)C44—C43—N4—C4954.9 (5)
C42A—C33A—C34A—C29A179.5 (15)C48—C43—N4—C49124.8 (5)
C30A—C29A—C34A—C33A3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.87 (3)1.96 (3)2.822 (4)168 (4)
N2—H2N···O10.84 (3)2.06 (3)2.848 (4)156 (5)
N3—H3N···O4ii0.86 (3)2.00 (3)2.829 (4)163 (4)
N4—H4N···O3i0.82 (3)2.04 (3)2.813 (4)156 (5)
Symmetry codes: (i) x1, y, z1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC14H13NO
Mr211.25
Crystal system, space groupMonoclinic, Cc
Temperature (K)299
a, b, c (Å)13.269 (2), 53.686 (6), 9.3921 (12)
β (°) 134.21 (1)
V3)4795.7 (10)
Z16
Radiation typeCu Kα
µ (mm1)0.58
Crystal size (mm)0.43 × 0.25 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9315, 4168, 3197
Rint0.028
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.129, 1.03
No. of reflections4168
No. of parameters653
No. of restraints110
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.13

Computer programs: CAD-4-PC (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.87 (3)1.96 (3)2.822 (4)168 (4)
N2—H2N···O10.84 (3)2.06 (3)2.848 (4)156 (5)
N3—H3N···O4ii0.86 (3)2.00 (3)2.829 (4)163 (4)
N4—H4N···O3i0.82 (3)2.04 (3)2.813 (4)156 (5)
Symmetry codes: (i) x1, y, z1; (ii) x+1, y, z.
 

Acknowledgements

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

References

First citationEnraf–Nonius (1996). CAD-4-PC. Enraf–Nonius, Delft, The Netherlands.
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationGowda, B. T., Jyothi, K., Paulus, H. & Fuess, H. (2003). Z. Naturforsch. Teil A, 58, 225–230.  CAS
First citationGowda, B. T., Tokarčík, M., Kožíšek, J., Sowmya, B. P. & Fuess, H. (2008). Acta Cryst. E64, o462.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals
First citationStoe & Cie (1987). REDU4. Stoe & Cie GmbH, Darmstadt, Germany.

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