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In the title compound, C14H11Cl2NO4, the dihedral angle between the two aromatic rings is 47.39 (13)°. The crystal packing is stabilized by C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806029035/jh2030sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806029035/jh2030Isup2.hkl
Contains datablock I

CCDC reference: 618252

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.143
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XPRESS (MacScience, 2002); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 2003).

4-(2,2-dichloro-N-methylacetamido)phenyl furan-2-carboxylate top
Crystal data top
C14H11Cl2NO4F(000) = 672
Mr = 328.14Dx = 1.522 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4433 reflections
a = 8.334 (5) Åθ = 2.3–25.0°
b = 10.778 (5) ŵ = 0.47 mm1
c = 16.412 (10) ÅT = 295 K
β = 103.761 (2)°Block, pale green
V = 1431.9 (14) Å30.25 × 0.24 × 0.22 mm
Z = 4
Data collection top
MacScience DIPLabo 32001
diffractometer
2209 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 2.3°
Detector resolution: 10.0 pixels mm-1h = 99
ω scansk = 1211
4433 measured reflectionsl = 1919
2524 independent reflections
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0816P)2 + 0.2846P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max < 0.001
2524 reflectionsΔρmax = 0.35 e Å3
192 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL97
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.056 (5)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2, conventional R-factors R are based on F, with F set to zero for negative F^2. The observed criterion of F^2 > σ(F^2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2 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
Cl200.83170 (9)0.22806 (7)0.22182 (4)0.0688 (3)
Cl210.60505 (12)0.43137 (7)0.17914 (5)0.0849 (3)
O30.23686 (19)0.04006 (16)0.20087 (11)0.0563 (5)
O70.10887 (19)0.07653 (15)0.05000 (11)0.0543 (5)
O80.05699 (17)0.10913 (14)0.11614 (10)0.0493 (5)
O180.9055 (2)0.38991 (18)0.08673 (12)0.0646 (6)
N150.6800 (2)0.32499 (17)0.00874 (11)0.0421 (5)
C10.2136 (3)0.1586 (3)0.16076 (16)0.0571 (8)
C20.1412 (3)0.0457 (2)0.15024 (13)0.0453 (7)
C40.3727 (3)0.0223 (3)0.24319 (17)0.0633 (9)
C50.3646 (3)0.1419 (3)0.22166 (17)0.0639 (9)
C60.0196 (2)0.0093 (2)0.09945 (13)0.0431 (6)
C90.2162 (2)0.1551 (2)0.08289 (13)0.0425 (6)
C100.3553 (3)0.0910 (2)0.09044 (14)0.0464 (7)
C110.5081 (3)0.1462 (2)0.06342 (14)0.0444 (6)
C120.5208 (2)0.26488 (19)0.03080 (13)0.0394 (6)
C130.3805 (3)0.3287 (2)0.02484 (16)0.0503 (7)
C140.2274 (3)0.2727 (2)0.05004 (17)0.0519 (8)
C160.7552 (3)0.3572 (3)0.07823 (16)0.0576 (8)
C170.7693 (3)0.3418 (2)0.07004 (14)0.0452 (7)
C190.6885 (3)0.2999 (2)0.13989 (14)0.0494 (7)
H10.173000.231900.133700.0690*
H40.459900.013600.282100.0760*
H50.442900.202700.242500.0770*
H100.346200.011700.113400.0560*
H110.602900.103400.067200.0530*
H130.388900.409200.003900.0600*
H140.132700.314500.044800.0620*
H16A0.827000.427300.062600.0860*
H16B0.670000.377500.127000.0860*
H16C0.817900.287900.090500.0860*
H190.599300.241400.116800.0590*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl200.0849 (5)0.0728 (5)0.0441 (4)0.0178 (3)0.0061 (3)0.0056 (3)
Cl210.1156 (7)0.0749 (5)0.0721 (5)0.0354 (4)0.0381 (5)0.0050 (4)
O30.0428 (8)0.0623 (10)0.0568 (10)0.0068 (7)0.0020 (7)0.0005 (8)
O70.0455 (9)0.0564 (9)0.0543 (9)0.0047 (7)0.0012 (7)0.0065 (8)
O80.0364 (8)0.0513 (9)0.0543 (9)0.0011 (6)0.0010 (6)0.0051 (7)
O180.0524 (10)0.0756 (12)0.0595 (11)0.0203 (9)0.0011 (8)0.0010 (9)
N150.0358 (9)0.0488 (10)0.0408 (9)0.0005 (7)0.0074 (7)0.0012 (7)
C10.0518 (13)0.0623 (14)0.0561 (14)0.0088 (11)0.0105 (11)0.0033 (11)
C20.0376 (11)0.0544 (12)0.0421 (11)0.0038 (9)0.0060 (9)0.0006 (9)
C40.0366 (11)0.092 (2)0.0546 (14)0.0030 (12)0.0024 (10)0.0044 (14)
C50.0455 (13)0.088 (2)0.0562 (15)0.0199 (13)0.0084 (11)0.0108 (14)
C60.0401 (10)0.0476 (11)0.0402 (11)0.0038 (9)0.0066 (9)0.0017 (9)
C90.0347 (10)0.0494 (11)0.0390 (10)0.0011 (8)0.0003 (8)0.0037 (9)
C100.0436 (11)0.0462 (11)0.0469 (12)0.0021 (9)0.0057 (9)0.0073 (9)
C110.0357 (10)0.0521 (12)0.0442 (11)0.0073 (8)0.0069 (8)0.0037 (9)
C120.0348 (10)0.0473 (11)0.0340 (10)0.0031 (8)0.0042 (8)0.0022 (8)
C130.0422 (12)0.0436 (11)0.0629 (14)0.0039 (9)0.0084 (10)0.0071 (10)
C140.0358 (11)0.0500 (13)0.0680 (15)0.0088 (9)0.0088 (10)0.0045 (11)
C160.0458 (12)0.0778 (17)0.0520 (13)0.0011 (11)0.0170 (10)0.0048 (12)
C170.0432 (11)0.0432 (11)0.0458 (12)0.0005 (9)0.0036 (9)0.0017 (9)
C190.0535 (13)0.0498 (12)0.0420 (12)0.0015 (10)0.0054 (10)0.0011 (10)
Geometric parameters (Å, º) top
Cl20—C191.752 (3)C10—C111.380 (4)
Cl21—C191.766 (3)C11—C121.381 (3)
O3—C21.366 (3)C12—C131.380 (3)
O3—C41.357 (3)C13—C141.383 (4)
O7—C61.204 (3)C17—C191.529 (3)
O8—C61.357 (3)C1—H10.9297
O8—C91.400 (3)C4—H40.9300
O18—C171.218 (3)C5—H50.9306
N15—C121.443 (3)C10—H100.9299
N15—C161.468 (3)C11—H110.9296
N15—C171.342 (3)C13—H130.9297
C1—C21.351 (4)C14—H140.9303
C1—C51.420 (4)C16—H16A0.9600
C2—C61.454 (3)C16—H16B0.9604
C4—C51.334 (5)C16—H16C0.9600
C9—C101.380 (3)C19—H190.9797
C9—C141.372 (3)
Cl20···O182.998 (3)C6···Cl20ii3.509 (3)
Cl20···Cl21i3.569 (2)C10···Cl20xi3.612 (3)
Cl20···O7ii3.395 (3)C10···O72.927 (3)
Cl20···C1ii3.635 (4)C10···C11ii3.583 (4)
Cl20···C6ii3.509 (3)C11···C10ii3.583 (4)
Cl20···C10iii3.612 (3)C11···O7ii3.375 (4)
Cl21···O183.252 (3)C13···Cl21v3.641 (3)
Cl21···N153.483 (3)C13···C193.270 (4)
Cl21···C133.599 (3)C13···Cl213.599 (3)
Cl21···Cl20iv3.569 (2)C16···C4xii3.550 (4)
Cl21···C13v3.641 (3)C17···O7ii3.078 (3)
Cl21···H133.1228C19···C133.270 (4)
Cl21···H5vi3.1065C5···H19vi3.0885
Cl21···H16Bv3.0491C6···H102.7944
O3···O82.620 (3)C11···H193.0511
O7···C11ii3.375 (4)C12···H192.3677
O7···C102.927 (3)C13···H192.7564
O7···N15ii3.223 (3)C16···H14xiii3.0967
O7···Cl20ii3.395 (3)C16···H113.0391
O7···O7vi3.182 (3)C17···H13v3.0721
O7···C17ii3.078 (3)H1···O18ii2.7653
O7···C6vi3.044 (3)H4···O18x2.4136
O8···O32.620 (3)H5···Cl21vi3.1065
O18···C4vii3.285 (4)H10···O72.6226
O18···Cl202.998 (3)H10···C62.7944
O18···Cl213.252 (3)H11···O3xiii2.9079
O3···H11viii2.9079H11···C163.0391
O7···H102.6226H11···O7ii2.7121
O7···H11ii2.7121H13···Cl213.1228
O8···H16Cviii2.8738H13···N15v2.9389
O18···H16A2.4154H13···C17v3.0721
O18···H1ii2.7653H14···C16viii3.0967
O18···H4vii2.4136H14···H16Cviii2.5674
N15···Cl213.483 (3)H16A···O182.4154
N15···O7ii3.223 (3)H16B···Cl21v3.0491
N15···H13v2.9389H16C···O8xiii2.8738
C1···Cl20ii3.635 (4)H16C···H14xiii2.5674
C4···C16ix3.550 (4)H19···C113.0511
C4···O18x3.285 (4)H19···C122.3677
C6···O7vi3.044 (3)H19···C132.7564
C6···C6vi3.363 (4)H19···C5vi3.0885
C2—O3—C4105.7 (2)Cl20—C19—Cl21109.28 (12)
C6—O8—C9119.74 (16)Cl20—C19—C17111.40 (18)
C12—N15—C16116.63 (18)Cl21—C19—C17108.56 (15)
C12—N15—C17124.64 (18)C2—C1—H1127.13
C16—N15—C17118.38 (19)C5—C1—H1127.21
C2—C1—C5105.7 (3)O3—C4—H4124.46
O3—C2—C1110.7 (2)C5—C4—H4124.47
O3—C2—C6119.43 (19)C1—C5—H5126.58
C1—C2—C6129.7 (2)C4—C5—H5126.60
O3—C4—C5111.1 (2)C9—C10—H10120.48
C1—C5—C4106.8 (3)C11—C10—H10120.44
O7—C6—O8124.56 (18)C10—C11—H11119.91
O7—C6—C2124.2 (2)C12—C11—H11119.84
O8—C6—C2111.27 (17)C12—C13—H13120.05
O8—C9—C10121.76 (19)C14—C13—H13120.06
O8—C9—C14116.73 (18)C9—C14—H14120.25
C10—C9—C14121.2 (2)C13—C14—H14120.24
C9—C10—C11119.1 (2)N15—C16—H16A109.44
C10—C11—C12120.3 (2)N15—C16—H16B109.50
N15—C12—C11119.62 (18)N15—C16—H16C109.47
N15—C12—C13120.16 (19)H16A—C16—H16B109.49
C11—C12—C13120.07 (19)H16A—C16—H16C109.43
C12—C13—C14119.9 (2)H16B—C16—H16C109.50
C9—C14—C13119.5 (2)Cl20—C19—H19109.16
O18—C17—N15123.2 (2)Cl21—C19—H19109.21
O18—C17—C19120.7 (2)C17—C19—H19109.21
N15—C17—C19116.1 (2)
C4—O3—C2—C10.5 (3)C1—C2—C6—O8170.3 (2)
C4—O3—C2—C6176.6 (2)O3—C2—C6—O7176.2 (2)
C2—O3—C4—C50.5 (3)C1—C2—C6—O78.5 (4)
C6—O8—C9—C14136.6 (2)O3—C4—C5—C10.4 (3)
C9—O8—C6—C2170.57 (17)C10—C9—C14—C130.7 (4)
C6—O8—C9—C1049.9 (3)O8—C9—C14—C13172.8 (2)
C9—O8—C6—O78.3 (3)C14—C9—C10—C110.8 (3)
C16—N15—C17—C19176.7 (2)O8—C9—C10—C11174.0 (2)
C16—N15—C17—O184.9 (3)C9—C10—C11—C121.2 (3)
C12—N15—C17—C193.7 (3)C10—C11—C12—C130.2 (3)
C17—N15—C12—C11105.5 (3)C10—C11—C12—N15175.3 (2)
C17—N15—C12—C1379.0 (3)C11—C12—C13—C141.3 (4)
C16—N15—C12—C1167.6 (3)N15—C12—C13—C14176.8 (2)
C12—N15—C17—O18177.9 (2)C12—C13—C14—C91.7 (4)
C16—N15—C12—C13107.9 (3)N15—C17—C19—Cl2199.7 (2)
C2—C1—C5—C40.0 (3)O18—C17—C19—Cl2178.7 (3)
C5—C1—C2—O30.3 (3)N15—C17—C19—Cl20139.93 (18)
C5—C1—C2—C6175.9 (2)O18—C17—C19—Cl2041.6 (3)
O3—C2—C6—O84.9 (3)
Symmetry codes: (i) x+3/2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+1/2, y+1/2, z+1/2; (iv) x+3/2, y+1/2, z+1/2; (v) x+1, y+1, z; (vi) x, y, z; (vii) x+3/2, y+1/2, z+1/2; (viii) x1, y, z; (ix) x+1/2, y1/2, z1/2; (x) x3/2, y+1/2, z1/2; (xi) x1/2, y+1/2, z1/2; (xii) x+1/2, y+1/2, z1/2; (xiii) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O18x0.932.413.285 (4)156
Symmetry code: (x) x3/2, y+1/2, z1/2.
 

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