organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-Chloro-N-iso­propyl-N-phenyl­acetamide

aCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China, and bCollege of Life Sciences, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
*Correspondence e-mail: yuanms@nwsuaf.edu.cn

(Received 26 June 2010; accepted 8 July 2010; online 14 July 2010)

In the title compound, C11H14ClNO, the herbicide propachlor, there are significant differences between the three N—C bond lengths [N—Ccarbon­yl = 1.354 (3) Å, N—Cphen­yl = 1.444 (2) Å and N—Cisoprop­yl = 1.496 (3) Å], indicating the presence of π delocalization involving the carbonyl group. The N atom lies 0.074 (2) Å from the plane defined by the the three bonded C atoms.

Related literature

For studies of propachlor and its derivatives, see: Dhillon & Anderson (1972[Dhillon, N. S. & Anderson, J. L. (1972). Weed Res. 12, 182-189.]); Kleudgen (1980[Kleudgen, H. K. (1980). Weed Res. 20, 41-46.]).

[Scheme 1]

Experimental

Crystal data
  • C11H14ClNO

  • Mr = 211.68

  • Monoclinic, P 21 /n

  • a = 11.9190 (11) Å

  • b = 7.8042 (8) Å

  • c = 12.3789 (13) Å

  • β = 98.963 (1)°

  • V = 1137.4 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 298 K

  • 0.47 × 0.45 × 0.44 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.870, Tmax = 0.878

  • 5426 measured reflections

  • 2004 independent reflections

  • 1501 reflections with I > 2σ(I)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.111

  • S = 1.03

  • 2004 reflections

  • 130 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Propachlor (2-chloro-N-isopropyl-N-phenylacetamide) and its derivatives have been widely studied as a pre-emergent herbicide used to control broadleaf weeds and grasses (Dhillon et al., 1972; Kleudgen, 1980). Propachlor may also be used as a precursor in the synthesis of indole-2-one compounds and in the course of exploring new indole-2-one compounds, we synthesized the title compound C11H14ClNO (I), the structure of which is reported here.

In structure of (I) (Fig. 1), there are obvious differences between the three C—N bond lengths (N—Ccarbonyl, 1.354 (3) Å; N—Cphenyl, 1.444 (2) Å; N—Cisopropyl, 1.496 (3) Å, indicating the presence of π delocalization involving the carbonyl group. Also N1 lies close to the plane defined by the three bonded carbon atoms C1, C3 and C9 [0.074 (2) Å].

As expected, there are no classic hydrogen bonds in the structure (Fig. 2). However, there is a weak intermolecular aliphatic C11—H11A···O1i interaction [symmetry code: (i) -x + 1/2, y - 1/2, -z + 1/2] stabilizing the packing. This intermolecular hydrogen bond is characterized by the parameters 0.96 Å (C11—H11A) and 2.56 Å (H11A···O1i).

Related literature top

For studies of propachlor and its derivatives, see: Dhillon & Anderson (1972); Kleudgen (1980).

Experimental top

N-Isopropylbenzenamine (1.00 g, 7.41 mmol) was dissolved in toluene (5.0 mL) and cooled to 273 K, after which a solution of 2-chloroacetyl chloride (0.90 g, 8.03 mmol) in toluene (5.0 mL) was slowly added over 0.5 h. with stirring. The mixture was then refluxed for 2 h. then slowly cooled to room temperature over 8 h. Colorless block crystals of (I) were formed (1.33 g, yield 85%).

Refinement top

All H atoms were placed in geometrically calculated positions and refined using a riding model with C—Haromatic = 0.93 %A and C—Haliphatic = 0.96–0.97 %A, with Uiso = 1.2Ueq(C), or 1.5Ueq(C) for CH3 groups.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular comformation and atom numbering scheme for (I). Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The molecular packing of (I) viewed down the b axis of the unit cell.
2-Chloro-N-isopropyl-N-phenylacetamide top
Crystal data top
C11H14ClNOF(000) = 448
Mr = 211.68Dx = 1.236 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2899 reflections
a = 11.9190 (11) Åθ = 2.2–25.0°
b = 7.8042 (8) ŵ = 0.30 mm1
c = 12.3789 (13) ÅT = 298 K
β = 98.963 (1)°Block, colorless
V = 1137.4 (2) Å30.47 × 0.45 × 0.44 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
2004 independent reflections
Radiation source: fine-focus sealed tube1501 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ϕ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1412
Tmin = 0.870, Tmax = 0.878k = 98
5426 measured reflectionsl = 1414
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0469P)2 + 0.4408P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2004 reflectionsΔρmax = 0.21 e Å3
130 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.079 (5)
Crystal data top
C11H14ClNOV = 1137.4 (2) Å3
Mr = 211.68Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.9190 (11) ŵ = 0.30 mm1
b = 7.8042 (8) ÅT = 298 K
c = 12.3789 (13) Å0.47 × 0.45 × 0.44 mm
β = 98.963 (1)°
Data collection top
Bruker APEXII CCD
diffractometer
2004 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
1501 reflections with I > 2σ(I)
Tmin = 0.870, Tmax = 0.878Rint = 0.025
5426 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.03Δρmax = 0.21 e Å3
2004 reflectionsΔρmin = 0.19 e Å3
130 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*/Ueq
Cl10.57852 (5)0.22476 (9)0.44873 (5)0.0711 (3)
N10.25393 (14)0.3526 (2)0.40187 (13)0.0483 (4)
O10.40481 (14)0.4455 (2)0.32694 (12)0.0662 (5)
C10.36637 (17)0.3629 (3)0.39670 (16)0.0475 (5)
C20.44299 (18)0.2648 (3)0.48500 (18)0.0543 (6)
H2A0.40740.15660.49800.065*
H2B0.45200.33010.55250.065*
C30.21346 (16)0.2664 (3)0.49159 (15)0.0438 (5)
C40.17401 (18)0.0998 (3)0.47994 (18)0.0548 (6)
H40.17340.04230.41400.066*
C50.1354 (2)0.0186 (3)0.5666 (2)0.0674 (7)
H50.10970.09390.55920.081*
C60.1349 (2)0.1042 (4)0.6635 (2)0.0691 (7)
H60.10730.05040.72110.083*
C70.1751 (2)0.2691 (4)0.67528 (19)0.0701 (7)
H70.17570.32600.74140.084*
C80.21471 (19)0.3513 (3)0.58983 (17)0.0586 (6)
H80.24200.46290.59830.070*
C90.1714 (2)0.4559 (3)0.32459 (18)0.0641 (7)
H90.20830.48500.26150.077*
C100.1415 (3)0.6210 (3)0.3759 (3)0.0939 (10)
H10A0.10330.59640.43680.141*
H10B0.09260.68750.32280.141*
H10C0.20970.68450.40060.141*
C110.0654 (3)0.3538 (4)0.2827 (3)0.1013 (11)
H11A0.08650.24710.25300.152*
H11B0.01860.41790.22670.152*
H11C0.02400.33180.34180.152*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0516 (4)0.0819 (5)0.0834 (5)0.0023 (3)0.0212 (3)0.0015 (3)
N10.0526 (10)0.0511 (10)0.0426 (9)0.0058 (8)0.0115 (7)0.0076 (8)
O10.0760 (11)0.0647 (11)0.0635 (9)0.0032 (8)0.0288 (8)0.0168 (8)
C10.0592 (13)0.0403 (11)0.0455 (11)0.0013 (9)0.0157 (10)0.0021 (9)
C20.0477 (12)0.0591 (14)0.0588 (13)0.0012 (10)0.0167 (10)0.0089 (11)
C30.0410 (10)0.0493 (12)0.0420 (10)0.0039 (9)0.0091 (8)0.0049 (9)
C40.0519 (12)0.0549 (14)0.0582 (13)0.0021 (10)0.0106 (10)0.0024 (11)
C50.0572 (14)0.0606 (15)0.0859 (17)0.0076 (11)0.0157 (12)0.0164 (14)
C60.0581 (14)0.090 (2)0.0622 (15)0.0004 (13)0.0178 (11)0.0268 (15)
C70.0761 (17)0.091 (2)0.0456 (13)0.0016 (14)0.0178 (12)0.0005 (13)
C80.0685 (14)0.0576 (14)0.0514 (12)0.0041 (11)0.0150 (10)0.0015 (11)
C90.0692 (15)0.0715 (17)0.0521 (12)0.0177 (12)0.0110 (11)0.0201 (12)
C100.095 (2)0.0512 (16)0.122 (2)0.0114 (15)0.0266 (18)0.0041 (16)
C110.112 (2)0.078 (2)0.094 (2)0.0226 (18)0.0480 (18)0.0207 (17)
Geometric parameters (Å, º) top
Cl1—C21.771 (2)C6—C71.374 (4)
N1—C11.354 (3)C6—H60.9300
N1—C31.444 (2)C7—C81.381 (3)
N1—C91.496 (3)C7—H70.9300
O1—C11.222 (2)C8—H80.9300
C1—C21.518 (3)C9—C101.503 (4)
C2—H2A0.9700C9—C111.515 (4)
C2—H2B0.9700C9—H90.9800
C3—C41.383 (3)C10—H10A0.9600
C3—C81.383 (3)C10—H10B0.9600
C4—C51.385 (3)C10—H10C0.9600
C4—H40.9300C11—H11A0.9600
C5—C61.373 (4)C11—H11B0.9600
C5—H50.9300C11—H11C0.9600
C1—N1—C3121.03 (16)C6—C7—C8120.6 (2)
C1—N1—C9119.66 (17)C6—C7—H7119.7
C3—N1—C9118.53 (16)C8—C7—H7119.7
O1—C1—N1123.2 (2)C7—C8—C3119.5 (2)
O1—C1—C2121.67 (19)C7—C8—H8120.2
N1—C1—C2115.15 (16)C3—C8—H8120.2
C1—C2—Cl1112.14 (14)N1—C9—C10111.53 (19)
C1—C2—H2A109.2N1—C9—C11111.5 (2)
Cl1—C2—H2A109.2C10—C9—C11110.8 (2)
C1—C2—H2B109.2N1—C9—H9107.6
Cl1—C2—H2B109.2C10—C9—H9107.6
H2A—C2—H2B107.9C11—C9—H9107.6
C4—C3—C8119.95 (19)C9—C10—H10A109.5
C4—C3—N1120.46 (18)C9—C10—H10B109.5
C8—C3—N1119.59 (19)H10A—C10—H10B109.5
C3—C4—C5119.9 (2)C9—C10—H10C109.5
C3—C4—H4120.1H10A—C10—H10C109.5
C5—C4—H4120.1H10B—C10—H10C109.5
C6—C5—C4120.1 (2)C9—C11—H11A109.5
C6—C5—H5119.9C9—C11—H11B109.5
C4—C5—H5119.9H11A—C11—H11B109.5
C5—C6—C7120.0 (2)C9—C11—H11C109.5
C5—C6—H6120.0H11A—C11—H11C109.5
C7—C6—H6120.0H11B—C11—H11C109.5
C3—N1—C1—O1174.27 (19)N1—C3—C4—C5179.95 (19)
C9—N1—C1—O14.6 (3)C3—C4—C5—C60.8 (3)
C3—N1—C1—C25.3 (3)C4—C5—C6—C71.5 (4)
C9—N1—C1—C2174.98 (19)C5—C6—C7—C81.0 (4)
O1—C1—C2—Cl120.0 (3)C6—C7—C8—C30.1 (4)
N1—C1—C2—Cl1160.48 (15)C4—C3—C8—C70.8 (3)
C1—N1—C3—C498.8 (2)N1—C3—C8—C7179.5 (2)
C9—N1—C3—C491.4 (2)C1—N1—C9—C1096.3 (2)
C1—N1—C3—C881.0 (3)C3—N1—C9—C1073.7 (3)
C9—N1—C3—C888.8 (2)C1—N1—C9—C11139.2 (2)
C8—C3—C4—C50.3 (3)C3—N1—C9—C1150.8 (3)

Experimental details

Crystal data
Chemical formulaC11H14ClNO
Mr211.68
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)11.9190 (11), 7.8042 (8), 12.3789 (13)
β (°) 98.963 (1)
V3)1137.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.47 × 0.45 × 0.44
Data collection
DiffractometerBruker APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.870, 0.878
No. of measured, independent and
observed [I > 2σ(I)] reflections
5426, 2004, 1501
Rint0.025
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.111, 1.03
No. of reflections2004
No. of parameters130
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

This work was supported by the PhD Programs Foundation of the Ministry of Education of China (No. 20090204120033)

References

First citationBruker (1997). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDhillon, N. S. & Anderson, J. L. (1972). Weed Res. 12, 182–189.  CrossRef CAS Web of Science
First citationKleudgen, H. K. (1980). Weed Res. 20, 41–46.  CrossRef CAS Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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COMMUNICATIONS
ISSN: 2056-9890
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