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The title compound, C17H12ClNO3, displays the characteristic features of benzofuran derivatives. The molecule is not planar. Inter­molecular C—H...O inter­actions help to stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500975X/dn6210sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500975X/dn6210Isup2.hkl
Contains datablock I

CCDC reference: 270320

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.078
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

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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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(1-Benzofuran-2-yl)ethanone O-(2-chlorobenzoyl)oxime top
Crystal data top
C17H12ClNO3F(000) = 648
Mr = 313.73Dx = 1.424 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 31482 reflections
a = 11.9515 (9) Åθ = 1.7–27.9°
b = 8.1082 (4) ŵ = 0.27 mm1
c = 15.1665 (10) ÅT = 293 K
β = 95.359 (6)°Prism, colourless
V = 1463.29 (16) Å30.55 × 0.32 × 0.28 mm
Z = 4
Data collection top
Stoe IPDS-II
diffractometer
2869 independent reflections
Radiation source: fine-focus sealed tube2200 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.1°
φ scansh = 1414
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 109
Tmin = 0.883, Tmax = 0.951l = 1818
19932 measured reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0375P)2 + 0.1959P]
where P = (Fo2 + 2Fc2)/3
2869 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.19 e Å3
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*/UeqOcc. (<1)
C10.51878 (12)0.02682 (17)0.33058 (9)0.0423 (3)
C20.50631 (14)0.1873 (2)0.35761 (11)0.0529 (4)
H20.46570.21000.40560.063*
C30.55374 (15)0.3137 (2)0.31397 (11)0.0553 (4)
H30.54450.42200.33220.066*
C40.61474 (14)0.28166 (19)0.24346 (11)0.0517 (4)
H40.64760.36750.21440.062*
C50.62667 (13)0.12120 (19)0.21633 (10)0.0470 (4)
H50.66790.09990.16850.056*
C60.57883 (12)0.00996 (17)0.25836 (9)0.0396 (3)
C70.59367 (13)0.18110 (19)0.22729 (10)0.0449 (3)
C80.62596 (12)0.34602 (18)0.02647 (10)0.0439 (3)
C90.56332 (16)0.2223 (2)0.03152 (12)0.0605 (4)
H9A0.54370.13000.00360.091*0.50
H9B0.60970.18540.07600.091*0.50
H9C0.49620.27180.05950.091*0.50
H9D0.55600.26140.09150.091*0.50
H9E0.49000.20610.01200.091*0.50
H9F0.60350.11970.02840.091*0.50
C100.66357 (12)0.49610 (19)0.01405 (10)0.0443 (3)
C110.64548 (13)0.5544 (2)0.09754 (10)0.0497 (4)
H110.60530.50250.14520.060*
C120.69990 (13)0.7110 (2)0.09864 (10)0.0481 (4)
C130.71356 (16)0.8335 (2)0.16184 (12)0.0629 (5)
H130.68230.82180.22000.075*
C140.77446 (18)0.9716 (2)0.13537 (14)0.0700 (5)
H140.78401.05450.17640.084*
C150.82204 (16)0.9901 (2)0.04900 (13)0.0666 (5)
H150.86331.08480.03370.080*
C160.80987 (15)0.8726 (2)0.01439 (12)0.0566 (4)
H160.84130.88480.07250.068*
C170.74857 (12)0.73578 (19)0.01310 (10)0.0457 (3)
Cl10.45205 (4)0.12278 (5)0.38813 (3)0.06352 (15)
N10.64844 (11)0.33640 (16)0.11047 (9)0.0504 (3)
O10.59081 (13)0.30388 (14)0.26937 (8)0.0727 (4)
O20.61106 (10)0.18015 (13)0.13998 (7)0.0520 (3)
O30.72697 (9)0.60458 (13)0.03983 (6)0.0478 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0482 (8)0.0390 (8)0.0397 (8)0.0026 (6)0.0048 (6)0.0029 (6)
C20.0647 (10)0.0467 (9)0.0483 (9)0.0019 (8)0.0114 (7)0.0071 (7)
C30.0705 (11)0.0366 (8)0.0578 (10)0.0004 (8)0.0015 (8)0.0078 (8)
C40.0616 (10)0.0377 (8)0.0551 (10)0.0088 (7)0.0026 (8)0.0063 (7)
C50.0513 (8)0.0447 (8)0.0461 (8)0.0019 (7)0.0098 (7)0.0047 (7)
C60.0450 (8)0.0351 (7)0.0386 (7)0.0011 (6)0.0029 (6)0.0016 (6)
C70.0531 (9)0.0394 (8)0.0429 (8)0.0026 (7)0.0075 (7)0.0012 (7)
C80.0438 (8)0.0445 (8)0.0439 (8)0.0010 (6)0.0070 (6)0.0006 (7)
C90.0708 (11)0.0556 (10)0.0549 (10)0.0092 (9)0.0035 (8)0.0049 (8)
C100.0438 (8)0.0472 (8)0.0421 (8)0.0017 (6)0.0044 (6)0.0001 (7)
C110.0520 (9)0.0574 (9)0.0392 (8)0.0003 (8)0.0018 (7)0.0018 (7)
C120.0496 (8)0.0532 (9)0.0425 (8)0.0062 (7)0.0089 (6)0.0077 (7)
C130.0757 (12)0.0681 (12)0.0459 (9)0.0114 (10)0.0108 (8)0.0164 (8)
C140.0893 (14)0.0552 (11)0.0689 (12)0.0076 (10)0.0255 (10)0.0234 (10)
C150.0803 (13)0.0506 (10)0.0719 (13)0.0082 (9)0.0233 (10)0.0082 (9)
C160.0628 (10)0.0548 (10)0.0534 (10)0.0084 (8)0.0117 (8)0.0028 (8)
C170.0478 (8)0.0471 (8)0.0435 (8)0.0004 (7)0.0114 (6)0.0086 (7)
Cl10.0828 (3)0.0552 (2)0.0562 (3)0.0123 (2)0.0253 (2)0.0064 (2)
N10.0623 (8)0.0414 (7)0.0479 (8)0.0113 (6)0.0070 (6)0.0062 (6)
O10.1258 (12)0.0364 (6)0.0598 (7)0.0075 (6)0.0292 (7)0.0062 (6)
O20.0737 (7)0.0394 (5)0.0441 (6)0.0116 (5)0.0113 (5)0.0020 (5)
O30.0540 (6)0.0501 (6)0.0393 (5)0.0086 (5)0.0038 (5)0.0072 (5)
Geometric parameters (Å, º) top
C1—C21.376 (2)C9—H9D0.9600
C1—C61.397 (2)C9—H9E0.9600
C1—Cl11.7318 (14)C9—H9F0.9600
C2—C31.371 (2)C10—C111.350 (2)
C2—H20.9300C10—O31.3784 (18)
C3—C41.374 (2)C11—C121.428 (2)
C3—H30.9300C11—H110.9300
C4—C51.376 (2)C12—C171.386 (2)
C4—H40.9300C12—C131.400 (2)
C5—C61.390 (2)C13—C141.374 (3)
C5—H50.9300C13—H130.9300
C6—C71.481 (2)C14—C151.387 (3)
C7—O11.1848 (18)C14—H140.9300
C7—O21.3594 (18)C15—C161.371 (2)
C8—N11.2797 (19)C15—H150.9300
C8—C101.453 (2)C16—C171.372 (2)
C8—C91.489 (2)C16—H160.9300
C9—H9A0.9600C17—O31.3716 (17)
C9—H9B0.9600N1—O21.4290 (15)
C9—H9C0.9600
C2—C1—C6120.89 (13)H9B—C9—H9E141.1
C2—C1—Cl1116.37 (12)H9C—C9—H9E56.3
C6—C1—Cl1122.70 (11)H9D—C9—H9E109.5
C3—C2—C1120.11 (15)C8—C9—H9F109.5
C3—C2—H2119.9H9A—C9—H9F56.3
C1—C2—H2119.9H9B—C9—H9F56.3
C2—C3—C4120.51 (15)H9C—C9—H9F141.1
C2—C3—H3119.7H9D—C9—H9F109.5
C4—C3—H3119.7H9E—C9—H9F109.5
C3—C4—C5119.26 (15)C11—C10—O3111.33 (14)
C3—C4—H4120.4C11—C10—C8131.38 (15)
C5—C4—H4120.4O3—C10—C8117.27 (13)
C4—C5—C6121.85 (14)C10—C11—C12106.81 (14)
C4—C5—H5119.1C10—C11—H11126.6
C6—C5—H5119.1C12—C11—H11126.6
C5—C6—C1117.37 (13)C17—C12—C13118.20 (16)
C5—C6—C7120.27 (13)C17—C12—C11105.64 (13)
C1—C6—C7122.35 (13)C13—C12—C11136.16 (16)
O1—C7—O2122.97 (14)C14—C13—C12118.03 (17)
O1—C7—C6127.25 (14)C14—C13—H13121.0
O2—C7—C6109.77 (12)C12—C13—H13121.0
N1—C8—C10115.31 (13)C13—C14—C15121.56 (16)
N1—C8—C9126.45 (14)C13—C14—H14119.2
C10—C8—C9118.21 (14)C15—C14—H14119.2
C8—C9—H9A109.5C16—C15—C14121.75 (18)
C8—C9—H9B109.5C16—C15—H15119.1
H9A—C9—H9B109.5C14—C15—H15119.1
C8—C9—H9C109.5C15—C16—C17115.92 (17)
H9A—C9—H9C109.5C15—C16—H16122.0
H9B—C9—H9C109.5C17—C16—H16122.0
C8—C9—H9D109.5O3—C17—C16124.97 (14)
H9A—C9—H9D141.1O3—C17—C12110.50 (13)
H9B—C9—H9D56.3C16—C17—C12124.53 (14)
H9C—C9—H9D56.3C8—N1—O2108.85 (12)
C8—C9—H9E109.5C7—O2—N1112.38 (11)
H9A—C9—H9E56.3C17—O3—C10105.72 (11)
C6—C1—C2—C30.5 (3)C10—C11—C12—C13179.93 (18)
Cl1—C1—C2—C3178.13 (13)C17—C12—C13—C140.1 (2)
C1—C2—C3—C40.5 (3)C11—C12—C13—C14179.88 (18)
C2—C3—C4—C50.8 (3)C12—C13—C14—C150.4 (3)
C3—C4—C5—C60.1 (2)C13—C14—C15—C160.6 (3)
C4—C5—C6—C10.8 (2)C14—C15—C16—C170.4 (3)
C4—C5—C6—C7179.92 (14)C15—C16—C17—O3179.85 (15)
C2—C1—C6—C51.1 (2)C15—C16—C17—C120.0 (3)
Cl1—C1—C6—C5178.62 (11)C13—C12—C17—O3179.97 (13)
C2—C1—C6—C7179.83 (14)C11—C12—C17—O30.16 (17)
Cl1—C1—C6—C72.3 (2)C13—C12—C17—C160.1 (2)
C5—C6—C7—O1154.12 (18)C11—C12—C17—C16179.74 (15)
C1—C6—C7—O124.9 (3)C10—C8—N1—O2177.45 (12)
C5—C6—C7—O226.33 (19)C9—C8—N1—O24.4 (2)
C1—C6—C7—O2154.61 (14)O1—C7—O2—N112.3 (2)
N1—C8—C10—C11172.77 (17)C6—C7—O2—N1168.09 (12)
C9—C8—C10—C115.5 (3)C8—N1—O2—C7157.66 (13)
N1—C8—C10—O35.4 (2)C16—C17—O3—C10179.88 (15)
C9—C8—C10—O3176.34 (13)C12—C17—O3—C100.02 (16)
O3—C10—C11—C120.23 (18)C11—C10—O3—C170.13 (16)
C8—C10—C11—C12178.00 (15)C8—C10—O3—C17178.37 (13)
C10—C11—C12—C170.23 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.503.213 (2)134
C16—H16···O1ii0.932.553.427 (2)159
Symmetry codes: (i) x, y1, z; (ii) x+3/2, y+1/2, z+1/2.
 

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