Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031893/bt2422sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031893/bt2422Isup2.hkl |
CCDC reference: 657679
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
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).
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.
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).
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).
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.
C8H8ClNO | F(000) = 352 |
Mr = 169.60 | Dx = 1.382 Mg m−3 |
Orthorhombic, Pna21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2c -2n | Cell parameters from 25 reflections |
a = 9.7163 (7) Å | θ = 8.9–25.3° |
b = 12.8528 (9) Å | µ = 3.65 mm−1 |
c = 6.5282 (6) Å | T = 299 K |
V = 815.25 (11) Å3 | Rod, colourless |
Z = 4 | 0.33 × 0.10 × 0.08 mm |
Enraf-Nonius CAD-4 diffractometer | 706 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 66.8°, θmin = 5.7° |
ω/2θ scans | h = 0→11 |
Absorption correction: psi-scan (North et al., 1968) | k = −7→15 |
Tmin = 0.359, Tmax = 0.776 | l = −7→0 |
1260 measured reflections | 3 standard reflections every 120 min |
793 independent reflections | intensity decay: 1.0% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H 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 = 1.04 | Δρmax = 0.17 e Å−3 |
793 reflections | Δρmin = −0.23 e Å−3 |
105 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0070 (10) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), no Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.02 (2) |
C8H8ClNO | V = 815.25 (11) Å3 |
Mr = 169.60 | Z = 4 |
Orthorhombic, Pna21 | Cu Kα radiation |
a = 9.7163 (7) Å | µ = 3.65 mm−1 |
b = 12.8528 (9) Å | T = 299 K |
c = 6.5282 (6) Å | 0.33 × 0.10 × 0.08 mm |
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 = 0.776 | 3 standard reflections every 120 min |
1260 measured reflections | intensity decay: 1.0% |
793 independent reflections |
R[F2 > 2σ(F2)] = 0.030 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.084 | Δρmax = 0.17 e Å−3 |
S = 1.04 | Δρmin = −0.23 e Å−3 |
793 reflections | Absolute structure: Flack (1983), no Friedel pairs |
105 parameters | Absolute structure parameter: −0.02 (2) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Cl11 | 0.25877 (7) | 0.53871 (6) | 0.69773 (15) | 0.0595 (3) | |
O3 | 0.43707 (19) | 0.2559 (2) | −0.1534 (4) | 0.0730 (8) | |
N4 | 0.2176 (2) | 0.29176 (19) | −0.0645 (5) | 0.0432 (5) | |
H4N | 0.132 (3) | 0.277 (2) | −0.092 (6) | 0.052* | |
C1 | 0.2594 (3) | 0.1900 (3) | −0.3668 (6) | 0.0545 (8) | |
H1A | 0.1632 | 0.1758 | −0.3474 | 0.065* | |
H1B | 0.3085 | 0.1256 | −0.3811 | 0.065* | |
H1C | 0.2715 | 0.2311 | −0.4883 | 0.065* | |
C2 | 0.3137 (3) | 0.2483 (2) | −0.1857 (5) | 0.0460 (7) | |
C5 | 0.2355 (2) | 0.3493 (2) | 0.1167 (4) | 0.0396 (6) | |
C6 | 0.3619 (2) | 0.3811 (2) | 0.1933 (5) | 0.0468 (7) | |
H6 | 0.4424 | 0.3643 | 0.1237 | 0.056* | |
C7 | 0.3682 (2) | 0.4379 (2) | 0.3731 (5) | 0.0504 (8) | |
H7 | 0.4532 | 0.4580 | 0.4255 | 0.061* | |
C8 | 0.2495 (2) | 0.4648 (2) | 0.4747 (6) | 0.0448 (7) | |
C9 | 0.1231 (2) | 0.4346 (2) | 0.4013 (5) | 0.0495 (7) | |
H9 | 0.0431 | 0.4525 | 0.4710 | 0.059* | |
C10 | 0.1167 (2) | 0.3772 (2) | 0.2229 (5) | 0.0471 (7) | |
H10 | 0.0313 | 0.3567 | 0.1725 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl11 | 0.0594 (4) | 0.0668 (5) | 0.0524 (4) | −0.0019 (3) | −0.0033 (5) | −0.0122 (4) |
O3 | 0.0373 (11) | 0.1145 (18) | 0.0672 (16) | 0.0193 (11) | −0.0051 (11) | −0.0167 (15) |
N4 | 0.0293 (10) | 0.0544 (12) | 0.0459 (13) | 0.0007 (9) | −0.0018 (10) | −0.0021 (11) |
C1 | 0.0610 (17) | 0.0520 (15) | 0.0506 (18) | 0.0043 (12) | −0.0012 (14) | −0.0032 (15) |
C2 | 0.0379 (13) | 0.0543 (14) | 0.0458 (16) | 0.0066 (13) | 0.0005 (14) | 0.0073 (14) |
C5 | 0.0329 (11) | 0.0440 (13) | 0.0419 (14) | −0.0015 (10) | −0.0015 (11) | 0.0052 (12) |
C6 | 0.0302 (11) | 0.0603 (16) | 0.0499 (16) | −0.0028 (9) | 0.0021 (15) | −0.0046 (16) |
C7 | 0.0323 (11) | 0.0624 (16) | 0.057 (2) | −0.0061 (11) | −0.0061 (13) | −0.0020 (16) |
C8 | 0.0456 (15) | 0.0441 (14) | 0.0448 (16) | 0.0003 (10) | −0.0019 (12) | 0.0032 (13) |
C9 | 0.0345 (11) | 0.0619 (16) | 0.0521 (17) | 0.0016 (11) | 0.0060 (13) | −0.0049 (15) |
C10 | 0.0293 (11) | 0.0583 (15) | 0.0536 (19) | −0.0001 (10) | −0.0020 (11) | −0.0043 (15) |
Cl11—C8 | 1.741 (4) | C5—C10 | 1.393 (3) |
O3—C2 | 1.221 (3) | C6—C7 | 1.384 (5) |
N4—C2 | 1.345 (4) | C6—H6 | 0.9300 |
N4—C5 | 1.406 (4) | C7—C8 | 1.375 (4) |
N4—H4N | 0.87 (3) | C7—H7 | 0.9300 |
C1—C2 | 1.496 (5) | C8—C9 | 1.374 (4) |
C1—H1A | 0.9600 | C9—C10 | 1.380 (5) |
C1—H1B | 0.9600 | C9—H9 | 0.9300 |
C1—H1C | 0.9600 | C10—H10 | 0.9300 |
C5—C6 | 1.389 (3) | ||
C2—N4—C5 | 128.9 (2) | C7—C6—C5 | 120.0 (2) |
C2—N4—H4N | 117 (2) | C7—C6—H6 | 120.0 |
C5—N4—H4N | 114 (3) | C5—C6—H6 | 120.0 |
C2—C1—H1A | 109.5 | C8—C7—C6 | 120.3 (2) |
C2—C1—H1B | 109.5 | C8—C7—H7 | 119.8 |
H1A—C1—H1B | 109.5 | C6—C7—H7 | 119.8 |
C2—C1—H1C | 109.5 | C9—C8—C7 | 120.7 (3) |
H1A—C1—H1C | 109.5 | C9—C8—Cl11 | 119.5 (2) |
H1B—C1—H1C | 109.5 | C7—C8—Cl11 | 119.8 (2) |
O3—C2—N4 | 123.1 (3) | C8—C9—C10 | 119.1 (3) |
O3—C2—C1 | 121.5 (3) | C8—C9—H9 | 120.5 |
N4—C2—C1 | 115.3 (2) | C10—C9—H9 | 120.5 |
C6—C5—C10 | 118.6 (3) | C9—C10—C5 | 121.3 (2) |
C6—C5—N4 | 124.6 (2) | C9—C10—H10 | 119.3 |
C10—C5—N4 | 116.9 (2) | C5—C10—H10 | 119.3 |
C5—N4—C2—O3 | −1.7 (5) | C6—C7—C8—C9 | 1.0 (5) |
C5—N4—C2—C1 | 178.8 (3) | C6—C7—C8—Cl11 | −178.6 (2) |
C2—N4—C5—C6 | 7.1 (5) | C7—C8—C9—C10 | −0.5 (5) |
C2—N4—C5—C10 | −174.1 (3) | Cl11—C8—C9—C10 | 179.2 (2) |
C10—C5—C6—C7 | 1.0 (4) | C8—C9—C10—C5 | 0.2 (5) |
N4—C5—C6—C7 | 179.7 (3) | C6—C5—C10—C9 | −0.5 (4) |
C5—C6—C7—C8 | −1.3 (5) | N4—C5—C10—C9 | −179.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O3i | 0.87 (3) | 1.98 (3) | 2.853 (3) | 179 (3) |
Symmetry code: (i) x−1/2, −y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C8H8ClNO |
Mr | 169.60 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 299 |
a, b, c (Å) | 9.7163 (7), 12.8528 (9), 6.5282 (6) |
V (Å3) | 815.25 (11) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 3.65 |
Crystal size (mm) | 0.33 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 |
Absorption correction | Psi-scan (North et al., 1968) |
Tmin, Tmax | 0.359, 0.776 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1260, 793, 706 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.596 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.084, 1.04 |
No. of reflections | 793 |
No. of parameters | 105 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.17, −0.23 |
Absolute structure | Flack (1983), no Friedel pairs |
Absolute structure parameter | −0.02 (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.
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O3i | 0.87 (3) | 1.98 (3) | 2.853 (3) | 179 (3) |
Symmetry code: (i) x−1/2, −y+1/2, z. |
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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).