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In the title compound, C
14H
11Cl
2NO
4, 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
CCDC reference: 618252
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C14H11Cl2NO4 | F(000) = 672 |
Mr = 328.14 | Dx = 1.522 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4433 reflections |
a = 8.334 (5) Å | θ = 2.3–25.0° |
b = 10.778 (5) Å | µ = 0.47 mm−1 |
c = 16.412 (10) Å | T = 295 K |
β = 103.761 (2)° | Block, pale green |
V = 1431.9 (14) Å3 | 0.25 × 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 tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 2.3° |
Detector resolution: 10.0 pixels mm-1 | h = −9→9 |
ω scans | k = −12→11 |
4433 measured reflections | l = −19→19 |
2524 independent reflections | |
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)] = 0.040 | H-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 reflections | Δρmax = 0.35 e Å−3 |
192 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cl20 | 0.83170 (9) | 0.22806 (7) | 0.22182 (4) | 0.0688 (3) | |
Cl21 | 0.60505 (12) | 0.43137 (7) | 0.17914 (5) | 0.0849 (3) | |
O3 | −0.23686 (19) | 0.04006 (16) | −0.20087 (11) | 0.0563 (5) | |
O7 | 0.10887 (19) | −0.07653 (15) | −0.05000 (11) | 0.0543 (5) | |
O8 | 0.05699 (17) | 0.10913 (14) | −0.11614 (10) | 0.0493 (5) | |
O18 | 0.9055 (2) | 0.38991 (18) | 0.08673 (12) | 0.0646 (6) | |
N15 | 0.6800 (2) | 0.32499 (17) | −0.00874 (11) | 0.0421 (5) | |
C1 | −0.2136 (3) | −0.1586 (3) | −0.16076 (16) | 0.0571 (8) | |
C2 | −0.1412 (3) | −0.0457 (2) | −0.15024 (13) | 0.0453 (7) | |
C4 | −0.3727 (3) | −0.0223 (3) | −0.24319 (17) | 0.0633 (9) | |
C5 | −0.3646 (3) | −0.1419 (3) | −0.22166 (17) | 0.0639 (9) | |
C6 | 0.0196 (2) | −0.0093 (2) | −0.09945 (13) | 0.0431 (6) | |
C9 | 0.2162 (2) | 0.1551 (2) | −0.08289 (13) | 0.0425 (6) | |
C10 | 0.3553 (3) | 0.0910 (2) | −0.09044 (14) | 0.0464 (7) | |
C11 | 0.5081 (3) | 0.1462 (2) | −0.06342 (14) | 0.0444 (6) | |
C12 | 0.5208 (2) | 0.26488 (19) | −0.03080 (13) | 0.0394 (6) | |
C13 | 0.3805 (3) | 0.3287 (2) | −0.02484 (16) | 0.0503 (7) | |
C14 | 0.2274 (3) | 0.2727 (2) | −0.05004 (17) | 0.0519 (8) | |
C16 | 0.7552 (3) | 0.3572 (3) | −0.07823 (16) | 0.0576 (8) | |
C17 | 0.7693 (3) | 0.3418 (2) | 0.07004 (14) | 0.0452 (7) | |
C19 | 0.6885 (3) | 0.2999 (2) | 0.13989 (14) | 0.0494 (7) | |
H1 | −0.17300 | −0.23190 | −0.13370 | 0.0690* | |
H4 | −0.45990 | 0.01360 | −0.28210 | 0.0760* | |
H5 | −0.44290 | −0.20270 | −0.24250 | 0.0770* | |
H10 | 0.34620 | 0.01170 | −0.11340 | 0.0560* | |
H11 | 0.60290 | 0.10340 | −0.06720 | 0.0530* | |
H13 | 0.38890 | 0.40920 | −0.00390 | 0.0600* | |
H14 | 0.13270 | 0.31450 | −0.04480 | 0.0620* | |
H16A | 0.82700 | 0.42730 | −0.06260 | 0.0860* | |
H16B | 0.67000 | 0.37750 | −0.12700 | 0.0860* | |
H16C | 0.81790 | 0.28790 | −0.09050 | 0.0860* | |
H19 | 0.59930 | 0.24140 | 0.11680 | 0.0590* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl20 | 0.0849 (5) | 0.0728 (5) | 0.0441 (4) | 0.0178 (3) | 0.0061 (3) | 0.0056 (3) |
Cl21 | 0.1156 (7) | 0.0749 (5) | 0.0721 (5) | 0.0354 (4) | 0.0381 (5) | 0.0050 (4) |
O3 | 0.0428 (8) | 0.0623 (10) | 0.0568 (10) | 0.0068 (7) | −0.0020 (7) | 0.0005 (8) |
O7 | 0.0455 (9) | 0.0564 (9) | 0.0543 (9) | 0.0047 (7) | −0.0012 (7) | 0.0065 (8) |
O8 | 0.0364 (8) | 0.0513 (9) | 0.0543 (9) | 0.0011 (6) | −0.0010 (6) | 0.0051 (7) |
O18 | 0.0524 (10) | 0.0756 (12) | 0.0595 (11) | −0.0203 (9) | 0.0011 (8) | −0.0010 (9) |
N15 | 0.0358 (9) | 0.0488 (10) | 0.0408 (9) | −0.0005 (7) | 0.0074 (7) | 0.0012 (7) |
C1 | 0.0518 (13) | 0.0623 (14) | 0.0561 (14) | −0.0088 (11) | 0.0105 (11) | 0.0033 (11) |
C2 | 0.0376 (11) | 0.0544 (12) | 0.0421 (11) | 0.0038 (9) | 0.0060 (9) | 0.0006 (9) |
C4 | 0.0366 (11) | 0.092 (2) | 0.0546 (14) | 0.0030 (12) | −0.0024 (10) | −0.0044 (14) |
C5 | 0.0455 (13) | 0.088 (2) | 0.0562 (15) | −0.0199 (13) | 0.0084 (11) | −0.0108 (14) |
C6 | 0.0401 (10) | 0.0476 (11) | 0.0402 (11) | 0.0038 (9) | 0.0066 (9) | −0.0017 (9) |
C9 | 0.0347 (10) | 0.0494 (11) | 0.0390 (10) | 0.0011 (8) | 0.0003 (8) | 0.0037 (9) |
C10 | 0.0436 (11) | 0.0462 (11) | 0.0469 (12) | 0.0021 (9) | 0.0057 (9) | −0.0073 (9) |
C11 | 0.0357 (10) | 0.0521 (12) | 0.0442 (11) | 0.0073 (8) | 0.0069 (8) | −0.0037 (9) |
C12 | 0.0348 (10) | 0.0473 (11) | 0.0340 (10) | 0.0031 (8) | 0.0042 (8) | 0.0022 (8) |
C13 | 0.0422 (12) | 0.0436 (11) | 0.0629 (14) | 0.0039 (9) | 0.0084 (10) | −0.0071 (10) |
C14 | 0.0358 (11) | 0.0500 (13) | 0.0680 (15) | 0.0088 (9) | 0.0088 (10) | −0.0045 (11) |
C16 | 0.0458 (12) | 0.0778 (17) | 0.0520 (13) | −0.0011 (11) | 0.0170 (10) | 0.0048 (12) |
C17 | 0.0432 (11) | 0.0432 (11) | 0.0458 (12) | −0.0005 (9) | 0.0036 (9) | −0.0017 (9) |
C19 | 0.0535 (13) | 0.0498 (12) | 0.0420 (12) | −0.0015 (10) | 0.0054 (10) | −0.0011 (10) |
Geometric parameters (Å, º) top
Cl20—C19 | 1.752 (3) | C10—C11 | 1.380 (4) |
Cl21—C19 | 1.766 (3) | C11—C12 | 1.381 (3) |
O3—C2 | 1.366 (3) | C12—C13 | 1.380 (3) |
O3—C4 | 1.357 (3) | C13—C14 | 1.383 (4) |
O7—C6 | 1.204 (3) | C17—C19 | 1.529 (3) |
O8—C6 | 1.357 (3) | C1—H1 | 0.9297 |
O8—C9 | 1.400 (3) | C4—H4 | 0.9300 |
O18—C17 | 1.218 (3) | C5—H5 | 0.9306 |
N15—C12 | 1.443 (3) | C10—H10 | 0.9299 |
N15—C16 | 1.468 (3) | C11—H11 | 0.9296 |
N15—C17 | 1.342 (3) | C13—H13 | 0.9297 |
C1—C2 | 1.351 (4) | C14—H14 | 0.9303 |
C1—C5 | 1.420 (4) | C16—H16A | 0.9600 |
C2—C6 | 1.454 (3) | C16—H16B | 0.9604 |
C4—C5 | 1.334 (5) | C16—H16C | 0.9600 |
C9—C10 | 1.380 (3) | C19—H19 | 0.9797 |
C9—C14 | 1.372 (3) | | |
| | | |
Cl20···O18 | 2.998 (3) | C6···Cl20ii | 3.509 (3) |
Cl20···Cl21i | 3.569 (2) | C10···Cl20xi | 3.612 (3) |
Cl20···O7ii | 3.395 (3) | C10···O7 | 2.927 (3) |
Cl20···C1ii | 3.635 (4) | C10···C11ii | 3.583 (4) |
Cl20···C6ii | 3.509 (3) | C11···C10ii | 3.583 (4) |
Cl20···C10iii | 3.612 (3) | C11···O7ii | 3.375 (4) |
Cl21···O18 | 3.252 (3) | C13···Cl21v | 3.641 (3) |
Cl21···N15 | 3.483 (3) | C13···C19 | 3.270 (4) |
Cl21···C13 | 3.599 (3) | C13···Cl21 | 3.599 (3) |
Cl21···Cl20iv | 3.569 (2) | C16···C4xii | 3.550 (4) |
Cl21···C13v | 3.641 (3) | C17···O7ii | 3.078 (3) |
Cl21···H13 | 3.1228 | C19···C13 | 3.270 (4) |
Cl21···H5vi | 3.1065 | C5···H19vi | 3.0885 |
Cl21···H16Bv | 3.0491 | C6···H10 | 2.7944 |
O3···O8 | 2.620 (3) | C11···H19 | 3.0511 |
O7···C11ii | 3.375 (4) | C12···H19 | 2.3677 |
O7···C10 | 2.927 (3) | C13···H19 | 2.7564 |
O7···N15ii | 3.223 (3) | C16···H14xiii | 3.0967 |
O7···Cl20ii | 3.395 (3) | C16···H11 | 3.0391 |
O7···O7vi | 3.182 (3) | C17···H13v | 3.0721 |
O7···C17ii | 3.078 (3) | H1···O18ii | 2.7653 |
O7···C6vi | 3.044 (3) | H4···O18x | 2.4136 |
O8···O3 | 2.620 (3) | H5···Cl21vi | 3.1065 |
O18···C4vii | 3.285 (4) | H10···O7 | 2.6226 |
O18···Cl20 | 2.998 (3) | H10···C6 | 2.7944 |
O18···Cl21 | 3.252 (3) | H11···O3xiii | 2.9079 |
O3···H11viii | 2.9079 | H11···C16 | 3.0391 |
O7···H10 | 2.6226 | H11···O7ii | 2.7121 |
O7···H11ii | 2.7121 | H13···Cl21 | 3.1228 |
O8···H16Cviii | 2.8738 | H13···N15v | 2.9389 |
O18···H16A | 2.4154 | H13···C17v | 3.0721 |
O18···H1ii | 2.7653 | H14···C16viii | 3.0967 |
O18···H4vii | 2.4136 | H14···H16Cviii | 2.5674 |
N15···Cl21 | 3.483 (3) | H16A···O18 | 2.4154 |
N15···O7ii | 3.223 (3) | H16B···Cl21v | 3.0491 |
N15···H13v | 2.9389 | H16C···O8xiii | 2.8738 |
C1···Cl20ii | 3.635 (4) | H16C···H14xiii | 2.5674 |
C4···C16ix | 3.550 (4) | H19···C11 | 3.0511 |
C4···O18x | 3.285 (4) | H19···C12 | 2.3677 |
C6···O7vi | 3.044 (3) | H19···C13 | 2.7564 |
C6···C6vi | 3.363 (4) | H19···C5vi | 3.0885 |
| | | |
C2—O3—C4 | 105.7 (2) | Cl20—C19—Cl21 | 109.28 (12) |
C6—O8—C9 | 119.74 (16) | Cl20—C19—C17 | 111.40 (18) |
C12—N15—C16 | 116.63 (18) | Cl21—C19—C17 | 108.56 (15) |
C12—N15—C17 | 124.64 (18) | C2—C1—H1 | 127.13 |
C16—N15—C17 | 118.38 (19) | C5—C1—H1 | 127.21 |
C2—C1—C5 | 105.7 (3) | O3—C4—H4 | 124.46 |
O3—C2—C1 | 110.7 (2) | C5—C4—H4 | 124.47 |
O3—C2—C6 | 119.43 (19) | C1—C5—H5 | 126.58 |
C1—C2—C6 | 129.7 (2) | C4—C5—H5 | 126.60 |
O3—C4—C5 | 111.1 (2) | C9—C10—H10 | 120.48 |
C1—C5—C4 | 106.8 (3) | C11—C10—H10 | 120.44 |
O7—C6—O8 | 124.56 (18) | C10—C11—H11 | 119.91 |
O7—C6—C2 | 124.2 (2) | C12—C11—H11 | 119.84 |
O8—C6—C2 | 111.27 (17) | C12—C13—H13 | 120.05 |
O8—C9—C10 | 121.76 (19) | C14—C13—H13 | 120.06 |
O8—C9—C14 | 116.73 (18) | C9—C14—H14 | 120.25 |
C10—C9—C14 | 121.2 (2) | C13—C14—H14 | 120.24 |
C9—C10—C11 | 119.1 (2) | N15—C16—H16A | 109.44 |
C10—C11—C12 | 120.3 (2) | N15—C16—H16B | 109.50 |
N15—C12—C11 | 119.62 (18) | N15—C16—H16C | 109.47 |
N15—C12—C13 | 120.16 (19) | H16A—C16—H16B | 109.49 |
C11—C12—C13 | 120.07 (19) | H16A—C16—H16C | 109.43 |
C12—C13—C14 | 119.9 (2) | H16B—C16—H16C | 109.50 |
C9—C14—C13 | 119.5 (2) | Cl20—C19—H19 | 109.16 |
O18—C17—N15 | 123.2 (2) | Cl21—C19—H19 | 109.21 |
O18—C17—C19 | 120.7 (2) | C17—C19—H19 | 109.21 |
N15—C17—C19 | 116.1 (2) | | |
| | | |
C4—O3—C2—C1 | 0.5 (3) | C1—C2—C6—O8 | 170.3 (2) |
C4—O3—C2—C6 | 176.6 (2) | O3—C2—C6—O7 | 176.2 (2) |
C2—O3—C4—C5 | −0.5 (3) | C1—C2—C6—O7 | −8.5 (4) |
C6—O8—C9—C14 | −136.6 (2) | O3—C4—C5—C1 | 0.4 (3) |
C9—O8—C6—C2 | −170.57 (17) | C10—C9—C14—C13 | 0.7 (4) |
C6—O8—C9—C10 | 49.9 (3) | O8—C9—C14—C13 | −172.8 (2) |
C9—O8—C6—O7 | 8.3 (3) | C14—C9—C10—C11 | 0.8 (3) |
C16—N15—C17—C19 | −176.7 (2) | O8—C9—C10—C11 | 174.0 (2) |
C16—N15—C17—O18 | 4.9 (3) | C9—C10—C11—C12 | −1.2 (3) |
C12—N15—C17—C19 | −3.7 (3) | C10—C11—C12—C13 | 0.2 (3) |
C17—N15—C12—C11 | −105.5 (3) | C10—C11—C12—N15 | −175.3 (2) |
C17—N15—C12—C13 | 79.0 (3) | C11—C12—C13—C14 | 1.3 (4) |
C16—N15—C12—C11 | 67.6 (3) | N15—C12—C13—C14 | 176.8 (2) |
C12—N15—C17—O18 | 177.9 (2) | C12—C13—C14—C9 | −1.7 (4) |
C16—N15—C12—C13 | −107.9 (3) | N15—C17—C19—Cl21 | −99.7 (2) |
C2—C1—C5—C4 | 0.0 (3) | O18—C17—C19—Cl21 | 78.7 (3) |
C5—C1—C2—O3 | −0.3 (3) | N15—C17—C19—Cl20 | 139.93 (18) |
C5—C1—C2—C6 | −175.9 (2) | O18—C17—C19—Cl20 | −41.6 (3) |
O3—C2—C6—O8 | −4.9 (3) | | |
Symmetry codes: (i) −x+3/2, y−1/2, −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) x−1, y, z; (ix) −x+1/2, y−1/2, −z−1/2; (x) x−3/2, −y+1/2, z−1/2; (xi) x−1/2, −y+1/2, z−1/2; (xii) −x+1/2, y+1/2, −z−1/2; (xiii) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O18x | 0.93 | 2.41 | 3.285 (4) | 156 |
Symmetry code: (x) x−3/2, −y+1/2, z−1/2. |
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