In the title compound, C
8H
7Cl
2NO, 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
CCDC reference: 613378
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
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
C8H7Cl2NO | F(000) = 416 |
Mr = 204.05 | Dx = 1.485 Mg m−3 |
Orthorhombic, Pna21 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2c -2n | Cell parameters from 25 reflections |
a = 9.567 (1) Å | θ = 5.9–25.7° |
b = 24.116 (5) Å | µ = 6.00 mm−1 |
c = 3.9552 (6) Å | T = 299 K |
V = 912.5 (3) Å3 | Needle, colourless |
Z = 4 | 0.57 × 0.04 × 0.03 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 541 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.071 |
Graphite monochromator | θmax = 66.9°, θmin = 3.7° |
ω scans | h = 0→11 |
Absorption correction: ψ scan (North et al., 1968) | k = −28→1 |
Tmin = 0.945, Tmax = 0.996 | l = 0→4 |
959 measured reflections | 3 standard reflections every 120 min |
943 independent reflections | intensity decay: 2.2% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-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 reflections | Δρmax = 0.33 e Å−3 |
110 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cl11 | 0.3297 (2) | 0.07002 (8) | 0.7981 (8) | 0.0836 (8) | |
Cl12 | 0.8872 (2) | 0.04676 (9) | 0.7590 (10) | 0.0963 (9) | |
O3 | 0.4344 (5) | 0.24977 (19) | 0.216 (2) | 0.086 (2) | |
N4 | 0.6539 (5) | 0.2174 (2) | 0.276 (2) | 0.0536 (15) | |
H4N | 0.7388 | 0.2278 | 0.3019 | 0.064* | |
C1 | 0.6196 (9) | 0.3074 (3) | 0.032 (3) | 0.074 (2) | |
H1A | 0.6259 | 0.3354 | 0.2039 | 0.111* | |
H1B | 0.5600 | 0.3201 | −0.1467 | 0.111* | |
H1C | 0.7111 | 0.2999 | −0.0562 | 0.111* | |
C2 | 0.5605 (8) | 0.2558 (3) | 0.181 (2) | 0.058 (2) | |
C5 | 0.6322 (7) | 0.1665 (3) | 0.439 (2) | 0.0501 (19) | |
C6 | 0.5024 (8) | 0.1458 (3) | 0.524 (2) | 0.056 (2) | |
H6 | 0.4220 | 0.1659 | 0.4745 | 0.067* | |
C7 | 0.4927 (8) | 0.0950 (3) | 0.684 (3) | 0.059 (2) | |
C8 | 0.6095 (9) | 0.0636 (3) | 0.755 (3) | 0.069 (2) | |
H8 | 0.6014 | 0.0294 | 0.8621 | 0.083* | |
C9 | 0.7395 (8) | 0.0842 (3) | 0.662 (3) | 0.060 (2) | |
C10 | 0.7511 (8) | 0.1346 (3) | 0.510 (2) | 0.0551 (19) | |
H10 | 0.8390 | 0.1481 | 0.4516 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl11 | 0.0900 (14) | 0.0712 (11) | 0.0896 (17) | −0.0146 (11) | 0.023 (2) | 0.0003 (17) |
Cl12 | 0.0982 (15) | 0.0976 (16) | 0.093 (2) | 0.0405 (12) | −0.014 (2) | 0.0066 (19) |
O3 | 0.049 (3) | 0.075 (3) | 0.134 (8) | 0.008 (2) | 0.000 (5) | 0.011 (6) |
N4 | 0.044 (3) | 0.052 (3) | 0.065 (4) | −0.001 (2) | −0.002 (5) | −0.007 (5) |
C1 | 0.081 (5) | 0.070 (5) | 0.070 (6) | 0.001 (4) | −0.004 (6) | 0.011 (5) |
C2 | 0.049 (4) | 0.059 (4) | 0.065 (6) | 0.007 (4) | −0.005 (5) | −0.006 (5) |
C5 | 0.047 (4) | 0.055 (4) | 0.048 (4) | −0.004 (3) | −0.006 (4) | −0.007 (4) |
C6 | 0.056 (4) | 0.056 (4) | 0.056 (5) | 0.004 (3) | −0.002 (4) | −0.003 (4) |
C7 | 0.078 (5) | 0.050 (4) | 0.049 (5) | −0.003 (4) | 0.006 (5) | −0.005 (4) |
C8 | 0.108 (6) | 0.047 (4) | 0.053 (6) | 0.009 (4) | 0.006 (7) | −0.004 (5) |
C9 | 0.072 (5) | 0.057 (5) | 0.052 (5) | 0.007 (4) | −0.007 (5) | −0.002 (4) |
C10 | 0.054 (4) | 0.060 (4) | 0.051 (5) | −0.001 (4) | −0.003 (4) | −0.013 (4) |
Geometric parameters (Å, º) top
Cl11—C7 | 1.731 (8) | C5—C6 | 1.380 (10) |
Cl12—C9 | 1.720 (8) | C5—C10 | 1.400 (10) |
O3—C2 | 1.223 (8) | C6—C7 | 1.381 (10) |
N4—C2 | 1.340 (9) | C6—H6 | 0.9300 |
N4—C5 | 1.402 (9) | C7—C8 | 1.380 (10) |
N4—H4N | 0.8571 | C8—C9 | 1.389 (11) |
C1—C2 | 1.488 (10) | C8—H8 | 0.9300 |
C1—H1A | 0.9600 | C9—C10 | 1.362 (10) |
C1—H1B | 0.9600 | C10—H10 | 0.9300 |
C1—H1C | 0.9600 | | |
| | | |
C2—N4—C5 | 129.4 (6) | C5—C6—C7 | 119.5 (7) |
C2—N4—H4N | 117.6 | C5—C6—H6 | 120.3 |
C5—N4—H4N | 110.1 | C7—C6—H6 | 120.3 |
C2—C1—H1A | 109.5 | C8—C7—C6 | 121.7 (8) |
C2—C1—H1B | 109.5 | C8—C7—Cl11 | 119.0 (6) |
H1A—C1—H1B | 109.5 | C6—C7—Cl11 | 119.2 (6) |
C2—C1—H1C | 109.5 | C7—C8—C9 | 118.4 (8) |
H1A—C1—H1C | 109.5 | C7—C8—H8 | 120.8 |
H1B—C1—H1C | 109.5 | C9—C8—H8 | 120.8 |
O3—C2—N4 | 123.0 (7) | C10—C9—C8 | 120.6 (8) |
O3—C2—C1 | 121.2 (7) | C10—C9—Cl12 | 120.1 (7) |
N4—C2—C1 | 115.8 (7) | C8—C9—Cl12 | 119.3 (6) |
C6—C5—C10 | 119.0 (7) | C9—C10—C5 | 120.8 (8) |
C6—C5—N4 | 124.2 (6) | C9—C10—H10 | 119.6 |
C10—C5—N4 | 116.9 (6) | C5—C10—H10 | 119.6 |
| | | |
C5—N4—C2—O3 | −3.0 (16) | C6—C7—C8—C9 | 0.2 (15) |
C5—N4—C2—C1 | 176.2 (9) | Cl11—C7—C8—C9 | −180.0 (9) |
C2—N4—C5—C6 | 2.0 (14) | C7—C8—C9—C10 | 0.9 (15) |
C2—N4—C5—C10 | −179.7 (9) | C7—C8—C9—Cl12 | 178.1 (8) |
C10—C5—C6—C7 | 1.6 (12) | C8—C9—C10—C5 | −0.8 (14) |
N4—C5—C6—C7 | 179.9 (8) | Cl12—C9—C10—C5 | −177.9 (7) |
C5—C6—C7—C8 | −1.5 (13) | C6—C5—C10—C9 | −0.5 (12) |
C5—C6—C7—Cl11 | 178.7 (7) | N4—C5—C10—C9 | −178.9 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O3i | 0.86 | 1.98 | 2.808 (7) | 163 |
Symmetry code: (i) x+1/2, −y+1/2, z. |