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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o773.
Published online 2008 April 2. doi:  10.1107/S1600536808008131
PMCID: PMC2961337

2,4-Dichloro-N-cyclo­hexyl­benzamide

Abstract

In the title mol­ecule, C13H15Cl2NO, the cyclohexane ring adopts a chair conformation. The aromatic ring plane is oriented with respect to the N/O/C plane at a dihedral angle of 51.88 (7)°. In the crystal structure, inter­molecular N—H(...)O hydrogen bonds link the mol­ecules into infinite chains along the [010] direction.

Related literature

For related literature, see: Makino et al. (2001 [triangle], 2003 [triangle]); Ho et al. (2002 [triangle]); Zhichkin et al. (2007 [triangle]); Jackson et al. (1994 [triangle]); Capdeville et al. (2002 [triangle]); Manley et al. (2002 [triangle]); Igawa et al. (1999 [triangle]); Jones & Kuś (2004 [triangle]). For ring conformation puckering parameters, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o773-scheme1.jpg

Experimental

Crystal data

  • C13H15Cl2NO
  • M r = 272.16
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o773-efi1.jpg
  • a = 26.135 (3) Å
  • b = 4.9144 (6) Å
  • c = 20.449 (2) Å
  • β = 90.167 (3)°
  • V = 2626.4 (5) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.48 mm−1
  • T = 120 (2) K
  • 0.48 × 0.17 × 0.12 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.803, T max = 0.945
  • 10950 measured reflections
  • 3141 independent reflections
  • 2389 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.110
  • S = 1.02
  • 3141 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008131/hk2439sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808008131/hk2439Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-i-Azam University, Islamabad.

supplementary crystallographic information

Comment

The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), quinazoline-2,4-diones (Makino et al., 2001), benzodiazepine-2,5-diones (Ho et al., 2002) and 2,3-disubstituted-3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficancy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002). Pyridylmethyl containing benzanilides are vascular endothelial growth factor receptor and tyrosine kinase inhibitor (Manley et al., 2002). Furthermore, benzamides have been reported to have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999). We report herein the crystal structure of the title compound, (I).

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges. Ring A (C1–C6) is not planar, having total puckering amplitude, QT, of 0.575 (3) Å. It adopts chair conformation [[var phi] = -177.97 (2)° and θ = 176.74 (3)°] (Cremer & Pople, 1975). Ring B (C8–C13) is, of course, planar and it is oriented with respect to the (N1/O1/C7) plane at a dihedral angle of 51.88 (7)°. The N1—C7—C8—C9 torsion angle is -130.16 (18)°. In N-cyclohexyl-4-(methoxycarbonyl)benzamide (Jones & Kuś, 2004), the corresponding torsion angles are reported as -17.9 (2)° and -45.2 (2)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into infinite chains along the [010] direction (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

A mixture of 2,4-dichlorobenzoyl chloride (65.7 mmol), cyclohexyl amine (86.9 mmol) and pyridine (20 ml) was left at 298 K for 15 h. Then, water (100 ml) was added and the resulting precipitates were collected. Recrystallization of the precipitates from benzene gave the title compound (yield; 75%).

Refinement

H atoms were positioned geometrically, with N—H = 0.88 Å (for NH) and C—H = 0.95, 0.99 and 1.00 Å for aromatic, methylene and methine H and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
A packing diagram for (I). Hydrogen bonds are shown as dashed lines. H-atoms not involved in hydrogen bonding are omitted for clarity.

Crystal data

C13H15Cl2NOF000 = 1136
Mr = 272.16Dx = 1.377 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 978 reflections
a = 26.135 (3) Åθ = 2.5–25.9º
b = 4.9144 (6) ŵ = 0.48 mm1
c = 20.449 (2) ÅT = 120 (2) K
β = 90.167 (3)ºPrism, colorless
V = 2626.4 (5) Å30.48 × 0.17 × 0.12 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer3141 independent reflections
Radiation source: sealed tube2389 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 120(2) Kθmax = 27.9º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −34→34
Tmin = 0.803, Tmax = 0.945k = −6→6
10950 measured reflectionsl = −26→26

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.0561P)2 + 0.7836P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3141 reflectionsΔρmax = 0.33 e Å3
154 parametersΔρmin = −0.21 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 > 2sigma(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)

xyzUiso*/Ueq
Cl10.55602 (2)0.84379 (11)0.19724 (2)0.03406 (16)
Cl20.683870 (19)0.21813 (13)0.05939 (3)0.04287 (18)
O10.45551 (5)0.8154 (2)0.11531 (7)0.0276 (3)
N10.43595 (6)0.3718 (3)0.12891 (8)0.0251 (4)
H1B0.44810.20490.13030.030*
C10.38119 (6)0.4124 (4)0.13939 (10)0.0246 (4)
H1A0.37430.61260.14030.029*
C20.35016 (7)0.2882 (5)0.08417 (9)0.0309 (5)
H2A0.35680.09010.08210.037*
H2B0.36070.36980.04210.037*
C30.29284 (8)0.3379 (5)0.09487 (10)0.0375 (5)
H3A0.28580.53560.09270.045*
H3B0.27310.24800.05950.045*
C40.27550 (7)0.2290 (5)0.16035 (10)0.0333 (5)
H4A0.27800.02800.16020.040*
H4B0.23920.27840.16730.040*
C50.30768 (8)0.3422 (5)0.21592 (10)0.0382 (5)
H5A0.29730.25480.25750.046*
H5B0.30140.54010.22000.046*
C60.36460 (7)0.2927 (5)0.20447 (9)0.0317 (5)
H6A0.38470.37690.24030.038*
H6B0.37150.09460.20480.038*
C70.46841 (7)0.5748 (4)0.11741 (8)0.0193 (4)
C80.52252 (6)0.4894 (3)0.10407 (8)0.0179 (4)
C90.56448 (7)0.6043 (4)0.13615 (8)0.0214 (4)
C100.61389 (7)0.5236 (4)0.12231 (9)0.0256 (4)
H10A0.64210.60310.14470.031*
C110.62169 (7)0.3258 (4)0.07559 (9)0.0256 (4)
C120.58138 (7)0.2087 (4)0.04197 (9)0.0247 (4)
H12A0.58730.07400.00960.030*
C130.53219 (7)0.2924 (4)0.05662 (9)0.0213 (4)
H13A0.50420.21340.03370.026*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0376 (3)0.0338 (3)0.0307 (3)−0.0036 (2)−0.0058 (2)−0.0119 (2)
Cl20.0182 (2)0.0630 (4)0.0474 (3)0.0106 (2)0.0028 (2)0.0024 (3)
O10.0274 (7)0.0119 (7)0.0436 (8)0.0027 (5)0.0016 (6)0.0005 (6)
N10.0181 (8)0.0111 (7)0.0463 (10)0.0031 (6)0.0046 (7)−0.0003 (7)
C10.0170 (8)0.0140 (9)0.0428 (11)0.0028 (7)0.0061 (8)0.0019 (8)
C20.0229 (10)0.0470 (13)0.0229 (10)0.0073 (9)0.0017 (8)0.0067 (9)
C30.0219 (10)0.0570 (15)0.0335 (11)0.0077 (10)−0.0015 (9)0.0059 (10)
C40.0191 (9)0.0394 (13)0.0413 (12)−0.0002 (9)0.0046 (8)0.0033 (10)
C50.0295 (11)0.0534 (15)0.0318 (11)0.0005 (10)0.0091 (9)−0.0050 (10)
C60.0243 (10)0.0472 (14)0.0237 (9)−0.0002 (9)−0.0003 (8)−0.0091 (9)
C70.0220 (9)0.0160 (9)0.0199 (8)0.0007 (7)−0.0008 (7)−0.0017 (7)
C80.0202 (8)0.0142 (8)0.0195 (8)0.0000 (7)0.0002 (7)0.0041 (7)
C90.0254 (9)0.0178 (9)0.0209 (8)−0.0027 (7)−0.0007 (7)0.0025 (7)
C100.0207 (9)0.0320 (11)0.0242 (9)−0.0058 (8)−0.0045 (7)0.0053 (8)
C110.0170 (9)0.0342 (11)0.0256 (9)0.0044 (8)0.0023 (7)0.0070 (8)
C120.0239 (9)0.0269 (11)0.0235 (9)0.0047 (8)0.0016 (7)0.0003 (8)
C130.0190 (9)0.0206 (10)0.0244 (9)0.0006 (7)−0.0021 (7)−0.0008 (7)

Geometric parameters (Å, °)

Cl1—C91.7310 (19)C4—H4B0.9900
Cl2—C111.7419 (19)C5—C61.526 (3)
O1—C71.231 (2)C5—H5A0.9900
N1—C71.331 (2)C5—H5B0.9900
N1—C11.461 (2)C6—H6A0.9900
N1—H1B0.8800C6—H6B0.9900
C1—C21.517 (3)C7—C81.501 (2)
C1—C61.519 (3)C8—C131.394 (2)
C1—H1A1.0000C8—C91.396 (2)
C2—C31.534 (3)C9—C101.381 (3)
C2—H2A0.9900C10—C111.378 (3)
C2—H2B0.9900C10—H10A0.9500
C3—C41.513 (3)C11—C121.382 (3)
C3—H3A0.9900C12—C131.383 (3)
C3—H3B0.9900C12—H12A0.9500
C4—C51.518 (3)C13—H13A0.9500
C4—H4A0.9900
C7—N1—C1123.28 (15)C4—C5—H5B109.3
C7—N1—H1B118.4C6—C5—H5B109.3
C1—N1—H1B118.4H5A—C5—H5B108.0
N1—C1—C2110.95 (16)C1—C6—C5110.70 (17)
N1—C1—C6110.96 (16)C1—C6—H6A109.5
C2—C1—C6110.05 (15)C5—C6—H6A109.5
N1—C1—H1A108.3C1—C6—H6B109.5
C2—C1—H1A108.3C5—C6—H6B109.5
C6—C1—H1A108.3H6A—C6—H6B108.1
C1—C2—C3110.49 (17)O1—C7—N1123.48 (16)
C1—C2—H2A109.6O1—C7—C8121.36 (16)
C3—C2—H2A109.6N1—C7—C8115.11 (15)
C1—C2—H2B109.6C13—C8—C9117.66 (16)
C3—C2—H2B109.6C13—C8—C7119.55 (15)
H2A—C2—H2B108.1C9—C8—C7122.76 (15)
C4—C3—C2111.41 (16)C10—C9—C8121.43 (17)
C4—C3—H3A109.3C10—C9—Cl1117.70 (14)
C2—C3—H3A109.3C8—C9—Cl1120.82 (14)
C4—C3—H3B109.3C11—C10—C9119.00 (17)
C2—C3—H3B109.3C11—C10—H10A120.5
H3A—C3—H3B108.0C9—C10—H10A120.5
C3—C4—C5111.50 (18)C10—C11—C12121.64 (17)
C3—C4—H4A109.3C10—C11—Cl2119.08 (14)
C5—C4—H4A109.3C12—C11—Cl2119.28 (15)
C3—C4—H4B109.3C11—C12—C13118.43 (18)
C5—C4—H4B109.3C11—C12—H12A120.8
H4A—C4—H4B108.0C13—C12—H12A120.8
C4—C5—C6111.40 (17)C12—C13—C8121.83 (17)
C4—C5—H5A109.3C12—C13—H13A119.1
C6—C5—H5A109.3C8—C13—H13A119.1
C7—N1—C1—C2113.7 (2)N1—C7—C8—C9−130.16 (18)
C7—N1—C1—C6−123.64 (19)C13—C8—C9—C10−1.0 (3)
N1—C1—C2—C3−178.66 (16)C7—C8—C9—C10−179.29 (16)
C6—C1—C2—C358.1 (2)C13—C8—C9—Cl1−178.28 (13)
C1—C2—C3—C4−56.3 (2)C7—C8—C9—Cl13.4 (2)
C2—C3—C4—C554.1 (3)C8—C9—C10—C110.2 (3)
C3—C4—C5—C6−54.1 (3)Cl1—C9—C10—C11177.62 (14)
N1—C1—C6—C5178.53 (16)C9—C10—C11—C120.6 (3)
C2—C1—C6—C5−58.3 (2)C9—C10—C11—Cl2−178.55 (14)
C4—C5—C6—C156.2 (2)C10—C11—C12—C13−0.7 (3)
C1—N1—C7—O10.9 (3)Cl2—C11—C12—C13178.49 (14)
C1—N1—C7—C8−176.58 (16)C11—C12—C13—C8−0.1 (3)
O1—C7—C8—C13−126.00 (18)C9—C8—C13—C120.9 (3)
N1—C7—C8—C1351.5 (2)C7—C8—C13—C12179.29 (17)
O1—C7—C8—C952.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.881.952.796 (3)161

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2439).

References

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