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In the title compound [alternatively called N-(3-chloro­phenyl)-3-oxobutanamide], C10H10ClNO2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001145/is6034sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001145/is6034Isup2.hkl
Contains datablock I

CCDC reference: 264056

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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
C10H10ClNO2F(000) = 880
Mr = 211.64Dx = 1.381 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 702 reflections
a = 9.5485 (16) Åθ = 2.6–18.3°
b = 8.2197 (13) ŵ = 0.35 mm1
c = 25.940 (4) ÅT = 293 K
V = 2035.9 (6) Å3Plate, colourless
Z = 80.32 × 0.26 × 0.24 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
1988 independent reflections
Radiation source: sealed tube1285 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1111
Tmin = 0.90, Tmax = 0.92k = 710
10164 measured reflectionsl = 2931
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H-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 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.14 e Å3
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
xyzUiso*/Ueq
Cl10.58989 (7)0.23432 (7)0.52633 (2)0.0703 (2)
N10.42667 (13)0.25024 (16)0.71108 (5)0.0385 (3)
H10.51340.23640.71890.046*
O10.20787 (11)0.24572 (17)0.74412 (5)0.0572 (4)
O20.36625 (18)0.42013 (18)0.83242 (6)0.0734 (5)
C10.39771 (17)0.29927 (19)0.66060 (7)0.0339 (4)
C20.49338 (19)0.2525 (2)0.62307 (7)0.0410 (4)
H20.57190.19200.63200.049*
C30.4714 (2)0.2960 (2)0.57296 (7)0.0445 (5)
C40.3579 (2)0.3849 (2)0.55802 (8)0.0552 (5)
H40.34380.41350.52370.066*
C50.2656 (2)0.4300 (3)0.59573 (9)0.0561 (6)
H50.18750.49120.58660.067*
C60.28399 (19)0.3882 (2)0.64642 (7)0.0481 (5)
H60.21890.42060.67100.058*
C70.33240 (17)0.2223 (2)0.74891 (7)0.0361 (4)
C80.39229 (17)0.1587 (2)0.79803 (7)0.0387 (4)
H8A0.48850.12560.79210.046*
H8B0.33990.06320.80850.046*
C90.38898 (19)0.2817 (3)0.84083 (8)0.0499 (5)
C100.4198 (3)0.2174 (3)0.89323 (9)0.0753 (7)
H10A0.42160.30570.91750.113*
H10B0.50920.16400.89300.113*
H10C0.34850.14110.90300.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0908 (4)0.0710 (4)0.0491 (3)0.0327 (3)0.0127 (3)0.0063 (3)
N10.0163 (6)0.0550 (9)0.0442 (8)0.0007 (7)0.0000 (6)0.0040 (7)
O10.0204 (7)0.0863 (12)0.0650 (9)0.0015 (7)0.0033 (6)0.0052 (8)
O20.0871 (12)0.0517 (9)0.0814 (10)0.0124 (8)0.0154 (10)0.0107 (8)
C10.0261 (8)0.0312 (9)0.0444 (10)0.0028 (7)0.0063 (8)0.0013 (7)
C20.0264 (9)0.0473 (11)0.0492 (10)0.0041 (8)0.0019 (7)0.0014 (9)
C30.0429 (11)0.0485 (10)0.0420 (12)0.0009 (9)0.0006 (8)0.0003 (9)
C40.0573 (13)0.0587 (13)0.0497 (12)0.0054 (11)0.0189 (11)0.0073 (10)
C50.0462 (12)0.0575 (14)0.0645 (14)0.0161 (9)0.0183 (11)0.0032 (10)
C60.0367 (11)0.0554 (12)0.0523 (12)0.0097 (9)0.0101 (9)0.0048 (10)
C70.0267 (9)0.0366 (9)0.0450 (10)0.0019 (7)0.0022 (7)0.0050 (8)
C80.0266 (8)0.0406 (10)0.0489 (11)0.0005 (7)0.0033 (8)0.0102 (7)
C90.0366 (10)0.0527 (13)0.0605 (12)0.0069 (10)0.0064 (9)0.0054 (9)
C100.0644 (15)0.1007 (19)0.0609 (15)0.0202 (15)0.0061 (12)0.0081 (13)
Geometric parameters (Å, º) top
Cl1—C31.7322 (19)C4—H40.9300
N1—C71.351 (2)C5—C61.370 (3)
N1—C11.398 (2)C5—H50.9300
N1—H10.8600C6—H60.9300
O1—C71.2108 (19)C7—C81.491 (2)
O2—C91.179 (2)C8—C91.502 (3)
C1—C61.360 (2)C8—H8A0.9700
C1—C21.389 (2)C8—H8B0.9700
C2—C31.364 (3)C9—C101.488 (3)
C2—H20.9300C10—H10A0.9600
C3—C41.363 (3)C10—H10B0.9600
C4—C51.368 (3)C10—H10C0.9600
C7—N1—C1126.69 (14)C5—C6—H6120.1
C7—N1—H1116.7O1—C7—N1123.56 (17)
C1—N1—H1116.7O1—C7—C8121.33 (17)
C6—C1—C2118.95 (17)N1—C7—C8115.11 (14)
C6—C1—N1124.51 (16)C7—C8—C9112.82 (15)
C2—C1—N1116.54 (15)C7—C8—H8A109.0
C3—C2—C1119.61 (17)C9—C8—H8A109.0
C3—C2—H2120.2C7—C8—H8B109.0
C1—C2—H2120.2C9—C8—H8B109.0
C4—C3—C2122.25 (18)H8A—C8—H8B107.8
C4—C3—Cl1118.53 (15)O2—C9—C10123.3 (2)
C2—C3—Cl1119.22 (14)O2—C9—C8121.10 (18)
C3—C4—C5117.01 (19)C10—C9—C8115.62 (19)
C3—C4—H4121.5C9—C10—H10A109.5
C5—C4—H4121.5C9—C10—H10B109.5
C4—C5—C6122.40 (18)H10A—C10—H10B109.5
C4—C5—H5118.8C9—C10—H10C109.5
C6—C5—H5118.8H10A—C10—H10C109.5
C1—C6—C5119.78 (18)H10B—C10—H10C109.5
C1—C6—H6120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.092.9259 (18)163
Symmetry code: (i) x+1/2, y, z+3/2.
 

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