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In the title compound, C8H7Cl2NO, all bond lengths and angles are normal. The mol­ecular skeleton is essentially planar. The inter­molecular N—H...O hydrogen bonds link the mol­ecules into zigzag chains running along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015280/cv2214sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015280/cv2214Isup2.hkl
Contains datablock I

CCDC reference: 613378

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.055
  • wR factor = 0.152
  • Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 11
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.84
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.838 Tmax scaled 0.835 Tmin scaled 0.792 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 66.87 From the CIF: _reflns_number_total 943 Count of symmetry unique reflns 943 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 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

Computing details top

Data collection: CAD-4-PC (Nonius, 1996); 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) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-(3,5-Dichlorophenyl)acetamide top
Crystal data top
C8H7Cl2NOF(000) = 416
Mr = 204.05Dx = 1.485 Mg m3
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 9.567 (1) Åθ = 5.9–25.7°
b = 24.116 (5) ŵ = 6.00 mm1
c = 3.9552 (6) ÅT = 299 K
V = 912.5 (3) Å3Needle, colourless
Z = 40.57 × 0.04 × 0.03 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
541 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 66.9°, θmin = 3.7°
ω scansh = 011
Absorption correction: ψ scan
(North et al., 1968)
k = 281
Tmin = 0.945, Tmax = 0.996l = 04
959 measured reflections3 standard reflections every 120 min
943 independent reflections intensity decay: 2.2%
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)] = 0.055H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0804P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.010
943 reflectionsΔρmax = 0.33 e Å3
110 parametersΔρmin = 0.33 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (7)
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
Cl110.3297 (2)0.07002 (8)0.7981 (8)0.0836 (8)
Cl120.8872 (2)0.04676 (9)0.7590 (10)0.0963 (9)
O30.4344 (5)0.24977 (19)0.216 (2)0.086 (2)
N40.6539 (5)0.2174 (2)0.276 (2)0.0536 (15)
H4N0.73880.22780.30190.064*
C10.6196 (9)0.3074 (3)0.032 (3)0.074 (2)
H1A0.62590.33540.20390.111*
H1B0.56000.32010.14670.111*
H1C0.71110.29990.05620.111*
C20.5605 (8)0.2558 (3)0.181 (2)0.058 (2)
C50.6322 (7)0.1665 (3)0.439 (2)0.0501 (19)
C60.5024 (8)0.1458 (3)0.524 (2)0.056 (2)
H60.42200.16590.47450.067*
C70.4927 (8)0.0950 (3)0.684 (3)0.059 (2)
C80.6095 (9)0.0636 (3)0.755 (3)0.069 (2)
H80.60140.02940.86210.083*
C90.7395 (8)0.0842 (3)0.662 (3)0.060 (2)
C100.7511 (8)0.1346 (3)0.510 (2)0.0551 (19)
H100.83900.14810.45160.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl110.0900 (14)0.0712 (11)0.0896 (17)0.0146 (11)0.023 (2)0.0003 (17)
Cl120.0982 (15)0.0976 (16)0.093 (2)0.0405 (12)0.014 (2)0.0066 (19)
O30.049 (3)0.075 (3)0.134 (8)0.008 (2)0.000 (5)0.011 (6)
N40.044 (3)0.052 (3)0.065 (4)0.001 (2)0.002 (5)0.007 (5)
C10.081 (5)0.070 (5)0.070 (6)0.001 (4)0.004 (6)0.011 (5)
C20.049 (4)0.059 (4)0.065 (6)0.007 (4)0.005 (5)0.006 (5)
C50.047 (4)0.055 (4)0.048 (4)0.004 (3)0.006 (4)0.007 (4)
C60.056 (4)0.056 (4)0.056 (5)0.004 (3)0.002 (4)0.003 (4)
C70.078 (5)0.050 (4)0.049 (5)0.003 (4)0.006 (5)0.005 (4)
C80.108 (6)0.047 (4)0.053 (6)0.009 (4)0.006 (7)0.004 (5)
C90.072 (5)0.057 (5)0.052 (5)0.007 (4)0.007 (5)0.002 (4)
C100.054 (4)0.060 (4)0.051 (5)0.001 (4)0.003 (4)0.013 (4)
Geometric parameters (Å, º) top
Cl11—C71.731 (8)C5—C61.380 (10)
Cl12—C91.720 (8)C5—C101.400 (10)
O3—C21.223 (8)C6—C71.381 (10)
N4—C21.340 (9)C6—H60.9300
N4—C51.402 (9)C7—C81.380 (10)
N4—H4N0.8571C8—C91.389 (11)
C1—C21.488 (10)C8—H80.9300
C1—H1A0.9600C9—C101.362 (10)
C1—H1B0.9600C10—H100.9300
C1—H1C0.9600
C2—N4—C5129.4 (6)C5—C6—C7119.5 (7)
C2—N4—H4N117.6C5—C6—H6120.3
C5—N4—H4N110.1C7—C6—H6120.3
C2—C1—H1A109.5C8—C7—C6121.7 (8)
C2—C1—H1B109.5C8—C7—Cl11119.0 (6)
H1A—C1—H1B109.5C6—C7—Cl11119.2 (6)
C2—C1—H1C109.5C7—C8—C9118.4 (8)
H1A—C1—H1C109.5C7—C8—H8120.8
H1B—C1—H1C109.5C9—C8—H8120.8
O3—C2—N4123.0 (7)C10—C9—C8120.6 (8)
O3—C2—C1121.2 (7)C10—C9—Cl12120.1 (7)
N4—C2—C1115.8 (7)C8—C9—Cl12119.3 (6)
C6—C5—C10119.0 (7)C9—C10—C5120.8 (8)
C6—C5—N4124.2 (6)C9—C10—H10119.6
C10—C5—N4116.9 (6)C5—C10—H10119.6
C5—N4—C2—O33.0 (16)C6—C7—C8—C90.2 (15)
C5—N4—C2—C1176.2 (9)Cl11—C7—C8—C9180.0 (9)
C2—N4—C5—C62.0 (14)C7—C8—C9—C100.9 (15)
C2—N4—C5—C10179.7 (9)C7—C8—C9—Cl12178.1 (8)
C10—C5—C6—C71.6 (12)C8—C9—C10—C50.8 (14)
N4—C5—C6—C7179.9 (8)Cl12—C9—C10—C5177.9 (7)
C5—C6—C7—C81.5 (13)C6—C5—C10—C90.5 (12)
C5—C6—C7—Cl11178.7 (7)N4—C5—C10—C9178.9 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O3i0.861.982.808 (7)163
Symmetry code: (i) x+1/2, y+1/2, z.
 

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