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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o8.
Published online 2009 December 4. doi:  10.1107/S1600536809051228
PMCID: PMC2980071

3,5-Dichloro-N-(2-methyl­but-3-yn-2-yl)benzamide

Abstract

In the title compound, C12H11Cl2NO, the amide group is twisted by a dihedral angle of 31.98 (2)° with respect to the benzene ring. In the crystal structure, mol­ecules are linked via N—H(...)O hydrogen bonds, forming one-dimensional supra­molecular chains.

Related literature

For the chemistry of halogenated aromatic amide derivatives, see: Cirilli et al. (1997 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-000o8-scheme1.jpg

Experimental

Crystal data

  • C12H11Cl2NO
  • M r = 256.12
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-000o8-efi1.jpg
  • a = 12.227 (2) Å
  • b = 10.898 (2) Å
  • c = 10.170 (2) Å
  • β = 111.08 (3)°
  • V = 1264.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.49 mm−1
  • T = 298 K
  • 0.4 × 0.35 × 0.2 mm

Data collection

  • Rigaku Mercury2 diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.881, T max = 0.940
  • 12803 measured reflections
  • 2890 independent reflections
  • 2308 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.103
  • S = 1.07
  • 2890 reflections
  • 147 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051228/xu2695sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051228/xu2695Isup2.hkl

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

Acknowledgments

This work was supported by a start-up grant from Anyang Institute of Technology, China.

supplementary crystallographic information

Comment

Halogenated aromatic amide derivatives are an important class of chemical raw materials, which have found wide range of applications in agriculture as herbicides, in medicine as drugs, in coordination chemistry as ligand, and which are also used in industry. Recently, a series of halogenated aromatic amide compounds have been reported (Cirilli et al., 1997). As an extension of these work on the structural characterization, we report here the crystal structure of the title compound 3,5-dichloro-N-(2-methylbut-3-yn-2-yl)benzamide.

The crystal data show that in the title compound (Fig. 1), the amide group is rotated by 31.98 (2)° out of the plane of the benzene ring. All the bond length are within the normal range. The crystal packing is stabilized by N—H···O hydrogen bonds to form an infinite one-dimensional chain parallel to the c axis (Table 1).

Experimental

The purchased 3,5-dichloro-N-(2-methylbut-3-yn-2-yl)benzamide (3 mmol, 768 mg) was dissolved in chloroform (20 ml) and evaporated in the air, single crystals of the compound suitable for X-ray analysis were obtained from the solution.

Refinement

The acetylene H atom was located in a difference Fourier map and refined as riding in as-found relative position with Uiso(H) = 1.2Ueq(C). Other H atoms were placed in calculated positions and refined in riding mode with C–H = 0.93 (aromatic), 0.96 Å (methyl) and N–H = 0.86 Å, Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for the others.

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C12H11Cl2NOF(000) = 528
Mr = 256.12Dx = 1.345 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2308 reflections
a = 12.227 (2) Åθ = 3.6–27.5°
b = 10.898 (2) ŵ = 0.49 mm1
c = 10.170 (2) ÅT = 298 K
β = 111.08 (3)°Block, colourless
V = 1264.5 (4) Å30.4 × 0.35 × 0.2 mm
Z = 4

Data collection

Rigaku Mercury2 diffractometer2890 independent reflections
Radiation source: fine-focus sealed tube2308 reflections with I > 2σ(I)
graphiteRint = 0.031
Detector resolution: 13.6612 pixels mm-1θmax = 27.5°, θmin = 3.6°
ω scansh = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −14→14
Tmin = 0.881, Tmax = 0.940l = −13→13
12803 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0378P)2 + 0.5464P] where P = (Fo2 + 2Fc2)/3
2890 reflections(Δ/σ)max < 0.001
147 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = −0.29 e Å3

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 > 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)

xyzUiso*/Ueq
Cl10.50021 (8)0.45984 (9)0.16860 (9)0.0697 (3)
Cl20.35913 (8)0.74552 (7)0.50663 (10)0.0644 (3)
O10.20562 (18)0.29208 (18)0.52618 (18)0.0477 (5)
C10.2939 (2)0.5093 (2)0.4506 (3)0.0376 (6)
H1A0.25320.51950.51150.045*
C70.2183 (2)0.2973 (2)0.4121 (2)0.0349 (5)
C50.3539 (2)0.3825 (2)0.2953 (3)0.0387 (6)
H5A0.35240.30810.24990.046*
C60.2908 (2)0.3977 (2)0.3837 (2)0.0334 (5)
N10.1679 (2)0.2190 (2)0.3067 (2)0.0420 (5)
H1B0.18300.22710.23080.050*
C30.4220 (2)0.5918 (3)0.3399 (3)0.0433 (6)
H3A0.46600.65650.32530.052*
C20.3579 (2)0.6049 (2)0.4260 (3)0.0399 (6)
C40.4190 (2)0.4799 (3)0.2760 (3)0.0415 (6)
C80.0882 (3)0.1195 (2)0.3123 (3)0.0444 (6)
C11−0.0141 (3)0.1721 (3)0.3361 (3)0.0543 (8)
C100.0456 (3)0.0569 (3)0.1680 (3)0.0680 (10)
H10A0.00710.11600.09630.102*
H10B−0.0083−0.00750.16670.102*
H10C0.11140.02280.15030.102*
C12−0.0996 (4)0.2091 (4)0.3488 (5)0.0849 (12)
H12−0.17100.25300.36030.102*
C90.1506 (3)0.0267 (3)0.4266 (4)0.0707 (10)
H9A0.17260.06530.51730.106*
H9B0.2194−0.00290.41240.106*
H9C0.0990−0.04090.42220.106*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0835 (6)0.0804 (6)0.0687 (5)−0.0018 (5)0.0559 (5)0.0028 (4)
Cl20.0809 (6)0.0369 (4)0.0803 (6)−0.0041 (4)0.0351 (5)−0.0126 (4)
O10.0674 (13)0.0510 (11)0.0302 (9)−0.0099 (10)0.0240 (9)−0.0033 (8)
C10.0375 (14)0.0413 (14)0.0341 (13)0.0005 (11)0.0129 (11)−0.0027 (10)
C70.0394 (13)0.0373 (13)0.0280 (12)−0.0003 (10)0.0119 (10)−0.0009 (10)
C50.0443 (14)0.0413 (14)0.0314 (12)−0.0004 (11)0.0147 (11)−0.0025 (10)
C60.0329 (12)0.0388 (13)0.0259 (11)−0.0012 (10)0.0074 (9)−0.0004 (10)
N10.0537 (14)0.0465 (13)0.0299 (11)−0.0158 (10)0.0199 (10)−0.0063 (9)
C30.0435 (15)0.0432 (15)0.0422 (14)−0.0038 (12)0.0143 (12)0.0073 (12)
C20.0427 (14)0.0345 (13)0.0397 (14)0.0020 (11)0.0114 (11)−0.0016 (10)
C40.0428 (15)0.0511 (16)0.0343 (13)0.0021 (12)0.0186 (11)0.0052 (11)
C80.0569 (17)0.0405 (15)0.0376 (14)−0.0128 (12)0.0193 (13)−0.0036 (11)
C110.060 (2)0.0516 (18)0.0552 (18)−0.0166 (15)0.0249 (15)−0.0028 (14)
C100.091 (3)0.066 (2)0.0528 (19)−0.0371 (19)0.0325 (18)−0.0231 (16)
C120.070 (3)0.078 (3)0.114 (3)−0.013 (2)0.042 (2)−0.013 (2)
C90.089 (3)0.0462 (19)0.070 (2)−0.0042 (17)0.020 (2)0.0103 (16)

Geometric parameters (Å, °)

Cl1—C41.734 (3)C3—C21.377 (4)
Cl2—C21.736 (3)C3—H3A0.9300
O1—C71.226 (3)C8—C111.472 (4)
C1—C21.380 (4)C8—C91.522 (4)
C1—C61.387 (3)C8—C101.531 (4)
C1—H1A0.9300C11—C121.171 (5)
C7—N11.335 (3)C10—H10A0.9600
C7—C61.500 (3)C10—H10B0.9600
C5—C41.383 (4)C10—H10C0.9600
C5—C61.390 (3)C12—H121.0386
C5—H5A0.9300C9—H9A0.9600
N1—C81.473 (3)C9—H9B0.9600
N1—H1B0.8600C9—H9C0.9600
C3—C41.375 (4)
C2—C1—C6119.3 (2)C3—C4—Cl1119.0 (2)
C2—C1—H1A120.3C5—C4—Cl1118.8 (2)
C6—C1—H1A120.3C11—C8—N1109.4 (2)
O1—C7—N1123.5 (2)C11—C8—C9110.8 (3)
O1—C7—C6120.1 (2)N1—C8—C9111.2 (2)
N1—C7—C6116.5 (2)C11—C8—C10108.4 (3)
C4—C5—C6118.8 (2)N1—C8—C10107.0 (2)
C4—C5—H5A120.6C9—C8—C10109.9 (3)
C6—C5—H5A120.6C12—C11—C8175.9 (4)
C1—C6—C5119.9 (2)C8—C10—H10A109.5
C1—C6—C7117.3 (2)C8—C10—H10B109.5
C5—C6—C7122.8 (2)H10A—C10—H10B109.5
C7—N1—C8124.0 (2)C8—C10—H10C109.5
C7—N1—H1B118.0H10A—C10—H10C109.5
C8—N1—H1B118.0H10B—C10—H10C109.5
C4—C3—C2117.9 (2)C11—C12—H12172.7
C4—C3—H3A121.0C8—C9—H9A109.5
C2—C3—H3A121.0C8—C9—H9B109.5
C3—C2—C1121.8 (2)H9A—C9—H9B109.5
C3—C2—Cl2118.9 (2)C8—C9—H9C109.5
C1—C2—Cl2119.3 (2)H9A—C9—H9C109.5
C3—C4—C5122.2 (2)H9B—C9—H9C109.5
C2—C1—C6—C51.4 (4)C4—C3—C2—Cl2−179.4 (2)
C2—C1—C6—C7−179.0 (2)C6—C1—C2—C3−2.0 (4)
C4—C5—C6—C10.0 (4)C6—C1—C2—Cl2178.54 (19)
C4—C5—C6—C7−179.6 (2)C2—C3—C4—C50.3 (4)
O1—C7—C6—C1−30.5 (4)C2—C3—C4—Cl1−179.2 (2)
N1—C7—C6—C1147.8 (2)C6—C5—C4—C3−0.9 (4)
O1—C7—C6—C5149.1 (2)C6—C5—C4—Cl1178.65 (19)
N1—C7—C6—C5−32.6 (4)C7—N1—C8—C1159.8 (4)
O1—C7—N1—C82.1 (4)C7—N1—C8—C9−63.0 (4)
C6—C7—N1—C8−176.2 (2)C7—N1—C8—C10177.0 (3)
C4—C3—C2—C11.1 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O1i0.862.213.051 (3)168

Symmetry codes: (i) x, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2695).

References

  • Cirilli, R., Gaparrini, F., Villani, C., Gavuzzo, E. & Cirilli, M. (1997). Acta Cryst. C53, 1937–1939.
  • Rigaku (2005). CrystalClear Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography