The title compound, C17H15BrO4S, was synthesized from (2E)-1-(3-bromo-2-thienyl)-3-(2-furyl)prop-2-en-1-one and ethyl acetoacetate in an ethanol solution. Single crystals were obtained from an ethyl acetate/hexane mixture. The crystal packing is stabilized by van der Waals forces.
Supporting information
CCDC reference: 634069
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.090
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.94 Ratio
| Author Response: An attempt to refine C17 applying a split model did not
yield a satisfactory structure model.
|
PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.56 Ratio
| Author Response: see above.
|
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C16 - C17 ... 1.41 Ang.
2 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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 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: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: maXus (Mackay et al., 1999).
(8RS,9SR)-ethyl
4-(3-bromothien-2-yl)-6-(2-furyl)-2-oxocyclohex-3-ene-1-carboxylate
top
Crystal data top
C17H15BrO4S | F(000) = 800 |
Mr = 395.26 | Dx = 1.582 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 136 reflections |
a = 16.5539 (14) Å | θ = 4.1–20.6° |
b = 11.1125 (8) Å | µ = 2.62 mm−1 |
c = 9.1650 (5) Å | T = 300 K |
β = 100.098 (6)° | Irregular block, colourless |
V = 1659.8 (2) Å3 | 0.37 × 0.35 × 0.22 mm |
Z = 4 | |
Data collection top
Bruker–Nonius KappaCCD diffractometer | 2655 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
φ scans | θmax = 26.5°, θmin = 4.5° |
Absorption correction: numerical (HABITUS; Herrendorf & Bärnighausen, 1997) | h = −19→20 |
Tmin = 0.600, Tmax = 0.805 | k = −13→13 |
17471 measured reflections | l = −10→11 |
3390 independent reflections | |
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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.025P)2 + 1.728P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
3390 reflections | Δρmax = 0.31 e Å−3 |
208 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 1.07670 (2) | 0.26706 (3) | −0.00141 (4) | 0.05410 (13) | |
S1 | 1.04563 (5) | 0.53429 (8) | 0.33347 (9) | 0.0452 (2) | |
C5 | 0.92251 (17) | 0.4182 (2) | 0.1472 (3) | 0.0338 (6) | |
C4 | 1.01047 (18) | 0.4326 (3) | 0.1929 (3) | 0.0350 (6) | |
C9 | 0.78162 (18) | 0.4973 (3) | 0.1686 (3) | 0.0394 (7) | |
H9 | 0.7850 | 0.5650 | 0.1015 | 0.047* | |
O2 | 0.73316 (15) | 0.6521 (2) | 0.3160 (3) | 0.0651 (7) | |
C6 | 0.88879 (19) | 0.3613 (3) | 0.0225 (3) | 0.0411 (7) | |
H6 | 0.9234 | 0.3319 | −0.0389 | 0.049* | |
C3 | 1.07757 (19) | 0.3798 (3) | 0.1504 (3) | 0.0384 (7) | |
C11 | 0.72925 (18) | 0.5341 (3) | 0.2772 (4) | 0.0431 (7) | |
C10 | 0.86807 (17) | 0.4675 (3) | 0.2473 (3) | 0.0395 (7) | |
H10A | 0.8930 | 0.5399 | 0.2944 | 0.047* | |
H10B | 0.8647 | 0.4092 | 0.3247 | 0.047* | |
C7 | 0.8017 (2) | 0.3431 (3) | −0.0218 (3) | 0.0442 (7) | |
C1 | 1.14510 (19) | 0.5022 (3) | 0.3307 (4) | 0.0499 (8) | |
H1 | 1.1890 | 0.5382 | 0.3925 | 0.060* | |
C2 | 1.15341 (19) | 0.4184 (3) | 0.2285 (4) | 0.0479 (8) | |
H2 | 1.2037 | 0.3894 | 0.2117 | 0.057* | |
C8 | 0.74444 (17) | 0.3904 (3) | 0.0764 (3) | 0.0377 (6) | |
H8 | 0.7340 | 0.3260 | 0.1437 | 0.045* | |
C15 | 0.6643 (2) | 0.4234 (3) | −0.0217 (4) | 0.0527 (8) | |
C13 | 0.6539 (2) | 0.5617 (4) | 0.4510 (5) | 0.0713 (11) | |
H13 | 0.6196 | 0.5475 | 0.5194 | 0.086* | |
C12 | 0.6816 (2) | 0.4759 (3) | 0.3561 (4) | 0.0584 (9) | |
H12 | 0.6688 | 0.3944 | 0.3502 | 0.070* | |
C14 | 0.6862 (2) | 0.6645 (4) | 0.4231 (5) | 0.0745 (13) | |
H14 | 0.6782 | 0.7366 | 0.4701 | 0.089* | |
O1 | 0.77427 (17) | 0.2894 (3) | −0.1356 (3) | 0.0696 (8) | |
O4 | 0.61114 (15) | 0.3346 (2) | −0.0301 (3) | 0.0681 (7) | |
O3 | 0.65141 (18) | 0.5171 (3) | −0.0838 (3) | 0.0828 (9) | |
C16 | 0.5337 (3) | 0.3510 (5) | −0.1325 (6) | 0.1015 (18) | |
H16A | 0.5041 | 0.4192 | −0.1020 | 0.122* | |
H16B | 0.5442 | 0.3663 | −0.2317 | 0.122* | |
C17 | 0.4869 (4) | 0.2452 (7) | −0.1314 (9) | 0.167 (4) | |
H17A | 0.4361 | 0.2537 | −0.1995 | 0.250* | |
H17B | 0.4757 | 0.2317 | −0.0333 | 0.250* | |
H17C | 0.5170 | 0.1781 | −0.1605 | 0.250* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0618 (2) | 0.03980 (19) | 0.0638 (2) | 0.00686 (16) | 0.01969 (16) | −0.00661 (15) |
S1 | 0.0376 (4) | 0.0607 (5) | 0.0366 (4) | −0.0040 (4) | 0.0046 (3) | −0.0089 (3) |
C5 | 0.0380 (15) | 0.0308 (14) | 0.0322 (15) | −0.0020 (12) | 0.0052 (11) | 0.0053 (11) |
C4 | 0.0399 (16) | 0.0349 (15) | 0.0304 (14) | −0.0013 (12) | 0.0066 (11) | 0.0043 (11) |
C9 | 0.0359 (16) | 0.0363 (16) | 0.0447 (17) | −0.0030 (13) | 0.0032 (13) | −0.0006 (12) |
O2 | 0.0526 (15) | 0.0535 (15) | 0.0914 (19) | −0.0051 (12) | 0.0187 (13) | −0.0244 (13) |
C6 | 0.0429 (17) | 0.0428 (17) | 0.0385 (16) | −0.0034 (14) | 0.0100 (13) | −0.0039 (13) |
C3 | 0.0451 (17) | 0.0345 (15) | 0.0367 (16) | 0.0023 (13) | 0.0103 (13) | 0.0092 (12) |
C11 | 0.0297 (15) | 0.0428 (18) | 0.0539 (19) | 0.0021 (13) | −0.0005 (13) | −0.0075 (14) |
C10 | 0.0324 (15) | 0.0479 (18) | 0.0379 (16) | −0.0053 (13) | 0.0053 (12) | −0.0078 (13) |
C7 | 0.0516 (19) | 0.0360 (17) | 0.0434 (17) | −0.0142 (14) | 0.0037 (14) | −0.0042 (13) |
C1 | 0.0342 (16) | 0.069 (2) | 0.0439 (19) | −0.0039 (16) | 0.0009 (13) | 0.0032 (16) |
C2 | 0.0366 (17) | 0.058 (2) | 0.0508 (19) | 0.0073 (15) | 0.0113 (14) | 0.0118 (16) |
C8 | 0.0372 (16) | 0.0372 (16) | 0.0362 (16) | −0.0054 (13) | 0.0002 (12) | 0.0018 (12) |
C15 | 0.0474 (19) | 0.051 (2) | 0.054 (2) | −0.0050 (17) | −0.0056 (15) | −0.0021 (16) |
C13 | 0.050 (2) | 0.092 (3) | 0.076 (3) | 0.016 (2) | 0.0239 (19) | −0.010 (2) |
C12 | 0.050 (2) | 0.056 (2) | 0.073 (2) | 0.0045 (17) | 0.0194 (18) | −0.0051 (18) |
C14 | 0.052 (2) | 0.080 (3) | 0.094 (3) | 0.007 (2) | 0.020 (2) | −0.037 (3) |
O1 | 0.0653 (17) | 0.0819 (19) | 0.0602 (16) | −0.0233 (14) | 0.0070 (13) | −0.0333 (14) |
O4 | 0.0422 (13) | 0.0675 (17) | 0.0849 (19) | −0.0155 (13) | −0.0160 (12) | 0.0061 (14) |
O3 | 0.078 (2) | 0.0591 (18) | 0.095 (2) | −0.0009 (15) | −0.0306 (16) | 0.0207 (15) |
C16 | 0.053 (3) | 0.112 (4) | 0.120 (4) | −0.013 (3) | −0.038 (3) | 0.003 (3) |
C17 | 0.081 (4) | 0.197 (8) | 0.193 (7) | −0.074 (5) | −0.058 (4) | 0.069 (6) |
Geometric parameters (Å, º) top
Br1—C3 | 1.870 (3) | C7—C8 | 1.511 (4) |
S1—C1 | 1.689 (3) | C1—C2 | 1.345 (5) |
S1—C4 | 1.736 (3) | C1—H1 | 0.9300 |
C5—C6 | 1.339 (4) | C2—H2 | 0.9300 |
C5—C4 | 1.452 (4) | C8—C15 | 1.511 (4) |
C5—C10 | 1.498 (4) | C8—H8 | 0.9800 |
C4—C3 | 1.372 (4) | C15—O3 | 1.188 (4) |
C9—C11 | 1.488 (4) | C15—O4 | 1.315 (4) |
C9—C10 | 1.522 (4) | C13—C14 | 1.306 (6) |
C9—C8 | 1.524 (4) | C13—C12 | 1.420 (5) |
C9—H9 | 0.9800 | C13—H13 | 0.9300 |
O2—C11 | 1.357 (4) | C12—H12 | 0.9300 |
O2—C14 | 1.362 (5) | C14—H14 | 0.9300 |
C6—C7 | 1.442 (4) | O4—C16 | 1.461 (5) |
C6—H6 | 0.9300 | C16—C17 | 1.409 (7) |
C3—C2 | 1.399 (4) | C16—H16A | 0.9700 |
C11—C12 | 1.328 (5) | C16—H16B | 0.9700 |
C10—H10A | 0.9700 | C17—H17A | 0.9600 |
C10—H10B | 0.9700 | C17—H17B | 0.9600 |
C7—O1 | 1.218 (4) | C17—H17C | 0.9600 |
| | | |
C1—S1—C4 | 92.98 (16) | C1—C2—C3 | 112.1 (3) |
C6—C5—C4 | 123.0 (3) | C1—C2—H2 | 123.9 |
C6—C5—C10 | 119.3 (3) | C3—C2—H2 | 123.9 |
C4—C5—C10 | 117.6 (2) | C7—C8—C15 | 107.9 (3) |
C3—C4—C5 | 133.8 (3) | C7—C8—C9 | 111.5 (2) |
C3—C4—S1 | 107.9 (2) | C15—C8—C9 | 111.6 (3) |
C5—C4—S1 | 118.4 (2) | C7—C8—H8 | 108.6 |
C11—C9—C10 | 110.6 (2) | C15—C8—H8 | 108.6 |
C11—C9—C8 | 111.1 (2) | C9—C8—H8 | 108.6 |
C10—C9—C8 | 110.4 (2) | O3—C15—O4 | 124.5 (3) |
C11—C9—H9 | 108.2 | O3—C15—C8 | 124.3 (3) |
C10—C9—H9 | 108.2 | O4—C15—C8 | 111.2 (3) |
C8—C9—H9 | 108.2 | C14—C13—C12 | 106.3 (4) |
C11—O2—C14 | 106.3 (3) | C14—C13—H13 | 126.9 |
C5—C6—C7 | 123.6 (3) | C12—C13—H13 | 126.9 |
C5—C6—H6 | 118.2 | C11—C12—C13 | 107.1 (4) |
C7—C6—H6 | 118.2 | C11—C12—H12 | 126.5 |
C4—C3—C2 | 115.0 (3) | C13—C12—H12 | 126.5 |
C4—C3—Br1 | 126.7 (2) | C13—C14—O2 | 110.9 (3) |
C2—C3—Br1 | 118.4 (2) | C13—C14—H14 | 124.5 |
C12—C11—O2 | 109.5 (3) | O2—C14—H14 | 124.5 |
C12—C11—C9 | 134.6 (3) | C15—O4—C16 | 116.6 (3) |
O2—C11—C9 | 115.8 (3) | C17—C16—O4 | 108.2 (4) |
C5—C10—C9 | 114.0 (2) | C17—C16—H16A | 110.0 |
C5—C10—H10A | 108.8 | O4—C16—H16A | 110.0 |
C9—C10—H10A | 108.8 | C17—C16—H16B | 110.0 |
C5—C10—H10B | 108.8 | O4—C16—H16B | 110.0 |
C9—C10—H10B | 108.8 | H16A—C16—H16B | 108.4 |
H10A—C10—H10B | 107.7 | C16—C17—H17A | 109.5 |
O1—C7—C6 | 120.9 (3) | C16—C17—H17B | 109.5 |
O1—C7—C8 | 120.1 (3) | H17A—C17—H17B | 109.5 |
C6—C7—C8 | 119.0 (3) | C16—C17—H17C | 109.5 |
C2—C1—S1 | 112.1 (2) | H17A—C17—H17C | 109.5 |
C2—C1—H1 | 124.0 | H17B—C17—H17C | 109.5 |
S1—C1—H1 | 124.0 | | |