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In the title compound [alternatively called
N-(3-chlorophenyl)-3-oxobutanamide], C
10H
10ClNO
2, the C=O bond lengths are 1.2108 (19) and 1.179 (2) Å, which implies that the molecule is in the keto form. The crystal structure is stabilized by an N—H
O hydrogen bond.
Supporting information
CCDC reference: 264056
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.075
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
N-(3-chlorophenyl)-3-oxobutanamide
top
Crystal data top
C10H10ClNO2 | F(000) = 880 |
Mr = 211.64 | Dx = 1.381 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 702 reflections |
a = 9.5485 (16) Å | θ = 2.6–18.3° |
b = 8.2197 (13) Å | µ = 0.35 mm−1 |
c = 25.940 (4) Å | T = 293 K |
V = 2035.9 (6) Å3 | Plate, colourless |
Z = 8 | 0.32 × 0.26 × 0.24 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 1988 independent reflections |
Radiation source: sealed tube | 1285 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 26.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.90, Tmax = 0.92 | k = −7→10 |
10164 measured reflections | l = −29→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.03P)2] where P = (Fo2 + 2Fc2)/3 |
1988 reflections | (Δ/σ)max < 0.001 |
128 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
Special details top
Experimental. All commercially available reagents were used as supplied. Carbon, hydrogen and
nitrogen were determined using a Elementar Vario EL elemental analyzer.
Infrared spectra were recorded with KBr optics on a Nicolet AVATAR 360
spectrophotometer. Mass spectrum (FAB) was measured using a MASPEC II system
analyzer. |
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 | |
Cl1 | 0.58989 (7) | 0.23432 (7) | 0.52633 (2) | 0.0703 (2) | |
N1 | 0.42667 (13) | 0.25024 (16) | 0.71108 (5) | 0.0385 (3) | |
H1 | 0.5134 | 0.2364 | 0.7189 | 0.046* | |
O1 | 0.20787 (11) | 0.24572 (17) | 0.74412 (5) | 0.0572 (4) | |
O2 | 0.36625 (18) | 0.42013 (18) | 0.83242 (6) | 0.0734 (5) | |
C1 | 0.39771 (17) | 0.29927 (19) | 0.66060 (7) | 0.0339 (4) | |
C2 | 0.49338 (19) | 0.2525 (2) | 0.62307 (7) | 0.0410 (4) | |
H2 | 0.5719 | 0.1920 | 0.6320 | 0.049* | |
C3 | 0.4714 (2) | 0.2960 (2) | 0.57296 (7) | 0.0445 (5) | |
C4 | 0.3579 (2) | 0.3849 (2) | 0.55802 (8) | 0.0552 (5) | |
H4 | 0.3438 | 0.4135 | 0.5237 | 0.066* | |
C5 | 0.2656 (2) | 0.4300 (3) | 0.59573 (9) | 0.0561 (6) | |
H5 | 0.1875 | 0.4912 | 0.5866 | 0.067* | |
C6 | 0.28399 (19) | 0.3882 (2) | 0.64642 (7) | 0.0481 (5) | |
H6 | 0.2189 | 0.4206 | 0.6710 | 0.058* | |
C7 | 0.33240 (17) | 0.2223 (2) | 0.74891 (7) | 0.0361 (4) | |
C8 | 0.39229 (17) | 0.1587 (2) | 0.79803 (7) | 0.0387 (4) | |
H8A | 0.4885 | 0.1256 | 0.7921 | 0.046* | |
H8B | 0.3399 | 0.0632 | 0.8085 | 0.046* | |
C9 | 0.38898 (19) | 0.2817 (3) | 0.84083 (8) | 0.0499 (5) | |
C10 | 0.4198 (3) | 0.2174 (3) | 0.89323 (9) | 0.0753 (7) | |
H10A | 0.4216 | 0.3057 | 0.9175 | 0.113* | |
H10B | 0.5092 | 0.1640 | 0.8930 | 0.113* | |
H10C | 0.3485 | 0.1411 | 0.9030 | 0.113* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0908 (4) | 0.0710 (4) | 0.0491 (3) | 0.0327 (3) | 0.0127 (3) | 0.0063 (3) |
N1 | 0.0163 (6) | 0.0550 (9) | 0.0442 (8) | −0.0007 (7) | 0.0000 (6) | 0.0040 (7) |
O1 | 0.0204 (7) | 0.0863 (12) | 0.0650 (9) | 0.0015 (7) | 0.0033 (6) | 0.0052 (8) |
O2 | 0.0871 (12) | 0.0517 (9) | 0.0814 (10) | 0.0124 (8) | −0.0154 (10) | −0.0107 (8) |
C1 | 0.0261 (8) | 0.0312 (9) | 0.0444 (10) | −0.0028 (7) | −0.0063 (8) | −0.0013 (7) |
C2 | 0.0264 (9) | 0.0473 (11) | 0.0492 (10) | −0.0041 (8) | 0.0019 (7) | 0.0014 (9) |
C3 | 0.0429 (11) | 0.0485 (10) | 0.0420 (12) | −0.0009 (9) | 0.0006 (8) | −0.0003 (9) |
C4 | 0.0573 (13) | 0.0587 (13) | 0.0497 (12) | −0.0054 (11) | −0.0189 (11) | 0.0073 (10) |
C5 | 0.0462 (12) | 0.0575 (14) | 0.0645 (14) | 0.0161 (9) | −0.0183 (11) | 0.0032 (10) |
C6 | 0.0367 (11) | 0.0554 (12) | 0.0523 (12) | 0.0097 (9) | −0.0101 (9) | −0.0048 (10) |
C7 | 0.0267 (9) | 0.0366 (9) | 0.0450 (10) | 0.0019 (7) | 0.0022 (7) | −0.0050 (8) |
C8 | 0.0266 (8) | 0.0406 (10) | 0.0489 (11) | 0.0005 (7) | 0.0033 (8) | 0.0102 (7) |
C9 | 0.0366 (10) | 0.0527 (13) | 0.0605 (12) | 0.0069 (10) | −0.0064 (9) | 0.0054 (9) |
C10 | 0.0644 (15) | 0.1007 (19) | 0.0609 (15) | 0.0202 (15) | −0.0061 (12) | 0.0081 (13) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.7322 (19) | C4—H4 | 0.9300 |
N1—C7 | 1.351 (2) | C5—C6 | 1.370 (3) |
N1—C1 | 1.398 (2) | C5—H5 | 0.9300 |
N1—H1 | 0.8600 | C6—H6 | 0.9300 |
O1—C7 | 1.2108 (19) | C7—C8 | 1.491 (2) |
O2—C9 | 1.179 (2) | C8—C9 | 1.502 (3) |
C1—C6 | 1.360 (2) | C8—H8A | 0.9700 |
C1—C2 | 1.389 (2) | C8—H8B | 0.9700 |
C2—C3 | 1.364 (3) | C9—C10 | 1.488 (3) |
C2—H2 | 0.9300 | C10—H10A | 0.9600 |
C3—C4 | 1.363 (3) | C10—H10B | 0.9600 |
C4—C5 | 1.368 (3) | C10—H10C | 0.9600 |
| | | |
C7—N1—C1 | 126.69 (14) | C5—C6—H6 | 120.1 |
C7—N1—H1 | 116.7 | O1—C7—N1 | 123.56 (17) |
C1—N1—H1 | 116.7 | O1—C7—C8 | 121.33 (17) |
C6—C1—C2 | 118.95 (17) | N1—C7—C8 | 115.11 (14) |
C6—C1—N1 | 124.51 (16) | C7—C8—C9 | 112.82 (15) |
C2—C1—N1 | 116.54 (15) | C7—C8—H8A | 109.0 |
C3—C2—C1 | 119.61 (17) | C9—C8—H8A | 109.0 |
C3—C2—H2 | 120.2 | C7—C8—H8B | 109.0 |
C1—C2—H2 | 120.2 | C9—C8—H8B | 109.0 |
C4—C3—C2 | 122.25 (18) | H8A—C8—H8B | 107.8 |
C4—C3—Cl1 | 118.53 (15) | O2—C9—C10 | 123.3 (2) |
C2—C3—Cl1 | 119.22 (14) | O2—C9—C8 | 121.10 (18) |
C3—C4—C5 | 117.01 (19) | C10—C9—C8 | 115.62 (19) |
C3—C4—H4 | 121.5 | C9—C10—H10A | 109.5 |
C5—C4—H4 | 121.5 | C9—C10—H10B | 109.5 |
C4—C5—C6 | 122.40 (18) | H10A—C10—H10B | 109.5 |
C4—C5—H5 | 118.8 | C9—C10—H10C | 109.5 |
C6—C5—H5 | 118.8 | H10A—C10—H10C | 109.5 |
C1—C6—C5 | 119.78 (18) | H10B—C10—H10C | 109.5 |
C1—C6—H6 | 120.1 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.09 | 2.9259 (18) | 163 |
Symmetry code: (i) x+1/2, y, −z+3/2. |
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