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The structure of the title compound, C8H8ClNO, has already been reported [Subramanian (1966). Z. Kristallogr. 123, 222–234], but the positions of the H atoms have not been determined. It has now been refined with new intensity data to significantly higher precision and with all H atoms. The structure is closely related to N-(2-chloro­phen­yl)acetamide, N-(3-chloro­phen­yl)acetamide and other related amides, with similar bond parameters. The mol­ecules are linked into chains through N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031893/bt2422sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031893/bt2422Isup2.hkl
Contains datablock I

CCDC reference: 657679

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.030
  • wR factor = 0.084
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.55
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 66.81 From the CIF: _reflns_number_total 793 Count of symmetry unique reflns 792 Completeness (_total/calc) 100.13% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The structure of N-(4-chlorophenyl)-acetamide has been refined as part of a study on the systematization of the crystal structures of N-aromatic amides (Gowda et al., 2000; Gowda, Foro & Fuess, 2007; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007; Gowda, Svoboda & Fuess, 2007). The purpose is to have accurate values of the bond parameters for comparison with the other structures which have recently been determined. The structure of the title compound (Fig. 1) is closely related to N-(2-chlorophenyl)- acetamide, N-(3-chlorophenyl)-acetamide and other related amides, with similar bond parameters (Gowda et al., 2000; Gowda, Foro & Fuess, 2007; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007; Gowda, Svoboda & Fuess, 2007). The molecules are linked into chains through N—H···O hydrogen bonds (Fig. 2 & Table 1).

Related literature top

For related literature, see: Gowda et al. (2000, 2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek, Svoboda & Fuess (2007); Gowda, Kožíšek, Tokarčík & Fuess (2007); Gowda, Svoboda & Fuess (2007).

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 (Gowda et al., 2003). Single crystals of the title compound were obtained from an ethanolic solution.

Refinement top

The H atom of the NH group was located in a diffrerence map and its coordinates have been refined with Uiso(H) = 1.2 Ueq(N). The carbon-bound H atoms were positioned with idealized geometry and refined using a riding model, with C—H distances in the range 0.93–0.96 Å, with Uiso(H) = 1.2 Ueq(C).

Structure description top

The structure of N-(4-chlorophenyl)-acetamide has been refined as part of a study on the systematization of the crystal structures of N-aromatic amides (Gowda et al., 2000; Gowda, Foro & Fuess, 2007; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007; Gowda, Svoboda & Fuess, 2007). The purpose is to have accurate values of the bond parameters for comparison with the other structures which have recently been determined. The structure of the title compound (Fig. 1) is closely related to N-(2-chlorophenyl)- acetamide, N-(3-chlorophenyl)-acetamide and other related amides, with similar bond parameters (Gowda et al., 2000; Gowda, Foro & Fuess, 2007; Gowda, Kozisek, Svoboda & Fuess, 2007; Gowda, Kožíšek, Tokarčík & Fuess, 2007; Gowda, Svoboda & Fuess, 2007). The molecules are linked into chains through N—H···O hydrogen bonds (Fig. 2 & Table 1).

For related literature, see: Gowda et al. (2000, 2003); Gowda, Foro & Fuess (2007); Gowda, Kozisek, Svoboda & Fuess (2007); Gowda, Kožíšek, Tokarčík & Fuess (2007); Gowda, Svoboda & Fuess (2007).

Computing details top

Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labeling scheme. The displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of the title compound with hydrogen bonding shown as dashed lines.
N-(4-Chlorophenyl)acetamide top
Crystal data top
C8H8ClNOF(000) = 352
Mr = 169.60Dx = 1.382 Mg m3
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 9.7163 (7) Åθ = 8.9–25.3°
b = 12.8528 (9) ŵ = 3.65 mm1
c = 6.5282 (6) ÅT = 299 K
V = 815.25 (11) Å3Rod, colourless
Z = 40.33 × 0.10 × 0.08 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
706 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 66.8°, θmin = 5.7°
ω/2θ scansh = 011
Absorption correction: psi-scan
(North et al., 1968)
k = 715
Tmin = 0.359, Tmax = 0.776l = 70
1260 measured reflections3 standard reflections every 120 min
793 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0574P)2 + 0.0284P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max = 0.006
S = 1.04Δρmax = 0.17 e Å3
793 reflectionsΔρmin = 0.23 e Å3
105 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0070 (10)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), no Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (2)
Crystal data top
C8H8ClNOV = 815.25 (11) Å3
Mr = 169.60Z = 4
Orthorhombic, Pna21Cu Kα radiation
a = 9.7163 (7) ŵ = 3.65 mm1
b = 12.8528 (9) ÅT = 299 K
c = 6.5282 (6) Å0.33 × 0.10 × 0.08 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
706 reflections with I > 2σ(I)
Absorption correction: psi-scan
(North et al., 1968)
Rint = 0.027
Tmin = 0.359, Tmax = 0.7763 standard reflections every 120 min
1260 measured reflections intensity decay: 1.0%
793 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084Δρmax = 0.17 e Å3
S = 1.04Δρmin = 0.23 e Å3
793 reflectionsAbsolute structure: Flack (1983), no Friedel pairs
105 parametersAbsolute structure parameter: 0.02 (2)
1 restraint
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
Cl110.25877 (7)0.53871 (6)0.69773 (15)0.0595 (3)
O30.43707 (19)0.2559 (2)0.1534 (4)0.0730 (8)
N40.2176 (2)0.29176 (19)0.0645 (5)0.0432 (5)
H4N0.132 (3)0.277 (2)0.092 (6)0.052*
C10.2594 (3)0.1900 (3)0.3668 (6)0.0545 (8)
H1A0.16320.17580.34740.065*
H1B0.30850.12560.38110.065*
H1C0.27150.23110.48830.065*
C20.3137 (3)0.2483 (2)0.1857 (5)0.0460 (7)
C50.2355 (2)0.3493 (2)0.1167 (4)0.0396 (6)
C60.3619 (2)0.3811 (2)0.1933 (5)0.0468 (7)
H60.44240.36430.12370.056*
C70.3682 (2)0.4379 (2)0.3731 (5)0.0504 (8)
H70.45320.45800.42550.061*
C80.2495 (2)0.4648 (2)0.4747 (6)0.0448 (7)
C90.1231 (2)0.4346 (2)0.4013 (5)0.0495 (7)
H90.04310.45250.47100.059*
C100.1167 (2)0.3772 (2)0.2229 (5)0.0471 (7)
H100.03130.35670.17250.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl110.0594 (4)0.0668 (5)0.0524 (4)0.0019 (3)0.0033 (5)0.0122 (4)
O30.0373 (11)0.1145 (18)0.0672 (16)0.0193 (11)0.0051 (11)0.0167 (15)
N40.0293 (10)0.0544 (12)0.0459 (13)0.0007 (9)0.0018 (10)0.0021 (11)
C10.0610 (17)0.0520 (15)0.0506 (18)0.0043 (12)0.0012 (14)0.0032 (15)
C20.0379 (13)0.0543 (14)0.0458 (16)0.0066 (13)0.0005 (14)0.0073 (14)
C50.0329 (11)0.0440 (13)0.0419 (14)0.0015 (10)0.0015 (11)0.0052 (12)
C60.0302 (11)0.0603 (16)0.0499 (16)0.0028 (9)0.0021 (15)0.0046 (16)
C70.0323 (11)0.0624 (16)0.057 (2)0.0061 (11)0.0061 (13)0.0020 (16)
C80.0456 (15)0.0441 (14)0.0448 (16)0.0003 (10)0.0019 (12)0.0032 (13)
C90.0345 (11)0.0619 (16)0.0521 (17)0.0016 (11)0.0060 (13)0.0049 (15)
C100.0293 (11)0.0583 (15)0.0536 (19)0.0001 (10)0.0020 (11)0.0043 (15)
Geometric parameters (Å, º) top
Cl11—C81.741 (4)C5—C101.393 (3)
O3—C21.221 (3)C6—C71.384 (5)
N4—C21.345 (4)C6—H60.9300
N4—C51.406 (4)C7—C81.375 (4)
N4—H4N0.87 (3)C7—H70.9300
C1—C21.496 (5)C8—C91.374 (4)
C1—H1A0.9600C9—C101.380 (5)
C1—H1B0.9600C9—H90.9300
C1—H1C0.9600C10—H100.9300
C5—C61.389 (3)
C2—N4—C5128.9 (2)C7—C6—C5120.0 (2)
C2—N4—H4N117 (2)C7—C6—H6120.0
C5—N4—H4N114 (3)C5—C6—H6120.0
C2—C1—H1A109.5C8—C7—C6120.3 (2)
C2—C1—H1B109.5C8—C7—H7119.8
H1A—C1—H1B109.5C6—C7—H7119.8
C2—C1—H1C109.5C9—C8—C7120.7 (3)
H1A—C1—H1C109.5C9—C8—Cl11119.5 (2)
H1B—C1—H1C109.5C7—C8—Cl11119.8 (2)
O3—C2—N4123.1 (3)C8—C9—C10119.1 (3)
O3—C2—C1121.5 (3)C8—C9—H9120.5
N4—C2—C1115.3 (2)C10—C9—H9120.5
C6—C5—C10118.6 (3)C9—C10—C5121.3 (2)
C6—C5—N4124.6 (2)C9—C10—H10119.3
C10—C5—N4116.9 (2)C5—C10—H10119.3
C5—N4—C2—O31.7 (5)C6—C7—C8—C91.0 (5)
C5—N4—C2—C1178.8 (3)C6—C7—C8—Cl11178.6 (2)
C2—N4—C5—C67.1 (5)C7—C8—C9—C100.5 (5)
C2—N4—C5—C10174.1 (3)Cl11—C8—C9—C10179.2 (2)
C10—C5—C6—C71.0 (4)C8—C9—C10—C50.2 (5)
N4—C5—C6—C7179.7 (3)C6—C5—C10—C90.5 (4)
C5—C6—C7—C81.3 (5)N4—C5—C10—C9179.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O3i0.87 (3)1.98 (3)2.853 (3)179 (3)
Symmetry code: (i) x1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC8H8ClNO
Mr169.60
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)299
a, b, c (Å)9.7163 (7), 12.8528 (9), 6.5282 (6)
V3)815.25 (11)
Z4
Radiation typeCu Kα
µ (mm1)3.65
Crystal size (mm)0.33 × 0.10 × 0.08
Data collection
DiffractometerEnraf-Nonius CAD-4
Absorption correctionPsi-scan
(North et al., 1968)
Tmin, Tmax0.359, 0.776
No. of measured, independent and
observed [I > 2σ(I)] reflections
1260, 793, 706
Rint0.027
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.030, 0.084, 1.04
No. of reflections793
No. of parameters105
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.23
Absolute structureFlack (1983), no Friedel pairs
Absolute structure parameter0.02 (2)

Computer programs: CAD-4-PC (Enraf-Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O3i0.87 (3)1.98 (3)2.853 (3)179 (3)
Symmetry code: (i) x1/2, y+1/2, z.
 

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