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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052603/wn2095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052603/wn2095Isup2.hkl
Contains datablock I

CCDC reference: 634069

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](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

Computing details top

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
C17H15BrO4SF(000) = 800
Mr = 395.26Dx = 1.582 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 136 reflections
a = 16.5539 (14) Åθ = 4.1–20.6°
b = 11.1125 (8) ŵ = 2.62 mm1
c = 9.1650 (5) ÅT = 300 K
β = 100.098 (6)°Irregular block, colourless
V = 1659.8 (2) Å30.37 × 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 tubeRint = 0.060
φ scansθmax = 26.5°, θmin = 4.5°
Absorption correction: numerical
(HABITUS; Herrendorf & Bärnighausen, 1997)
h = 1920
Tmin = 0.600, Tmax = 0.805k = 1313
17471 measured reflectionsl = 1011
3390 independent 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)] = 0.037H-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 reflectionsΔρmax = 0.31 e Å3
208 parametersΔρmin = 0.45 e Å3
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
xyzUiso*/Ueq
Br11.07670 (2)0.26706 (3)0.00141 (4)0.05410 (13)
S11.04563 (5)0.53429 (8)0.33347 (9)0.0452 (2)
C50.92251 (17)0.4182 (2)0.1472 (3)0.0338 (6)
C41.01047 (18)0.4326 (3)0.1929 (3)0.0350 (6)
C90.78162 (18)0.4973 (3)0.1686 (3)0.0394 (7)
H90.78500.56500.10150.047*
O20.73316 (15)0.6521 (2)0.3160 (3)0.0651 (7)
C60.88879 (19)0.3613 (3)0.0225 (3)0.0411 (7)
H60.92340.33190.03890.049*
C31.07757 (19)0.3798 (3)0.1504 (3)0.0384 (7)
C110.72925 (18)0.5341 (3)0.2772 (4)0.0431 (7)
C100.86807 (17)0.4675 (3)0.2473 (3)0.0395 (7)
H10A0.89300.53990.29440.047*
H10B0.86470.40920.32470.047*
C70.8017 (2)0.3431 (3)0.0218 (3)0.0442 (7)
C11.14510 (19)0.5022 (3)0.3307 (4)0.0499 (8)
H11.18900.53820.39250.060*
C21.15341 (19)0.4184 (3)0.2285 (4)0.0479 (8)
H21.20370.38940.21170.057*
C80.74444 (17)0.3904 (3)0.0764 (3)0.0377 (6)
H80.73400.32600.14370.045*
C150.6643 (2)0.4234 (3)0.0217 (4)0.0527 (8)
C130.6539 (2)0.5617 (4)0.4510 (5)0.0713 (11)
H130.61960.54750.51940.086*
C120.6816 (2)0.4759 (3)0.3561 (4)0.0584 (9)
H120.66880.39440.35020.070*
C140.6862 (2)0.6645 (4)0.4231 (5)0.0745 (13)
H140.67820.73660.47010.089*
O10.77427 (17)0.2894 (3)0.1356 (3)0.0696 (8)
O40.61114 (15)0.3346 (2)0.0301 (3)0.0681 (7)
O30.65141 (18)0.5171 (3)0.0838 (3)0.0828 (9)
C160.5337 (3)0.3510 (5)0.1325 (6)0.1015 (18)
H16A0.50410.41920.10200.122*
H16B0.54420.36630.23170.122*
C170.4869 (4)0.2452 (7)0.1314 (9)0.167 (4)
H17A0.43610.25370.19950.250*
H17B0.47570.23170.03330.250*
H17C0.51700.17810.16050.250*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0618 (2)0.03980 (19)0.0638 (2)0.00686 (16)0.01969 (16)0.00661 (15)
S10.0376 (4)0.0607 (5)0.0366 (4)0.0040 (4)0.0046 (3)0.0089 (3)
C50.0380 (15)0.0308 (14)0.0322 (15)0.0020 (12)0.0052 (11)0.0053 (11)
C40.0399 (16)0.0349 (15)0.0304 (14)0.0013 (12)0.0066 (11)0.0043 (11)
C90.0359 (16)0.0363 (16)0.0447 (17)0.0030 (13)0.0032 (13)0.0006 (12)
O20.0526 (15)0.0535 (15)0.0914 (19)0.0051 (12)0.0187 (13)0.0244 (13)
C60.0429 (17)0.0428 (17)0.0385 (16)0.0034 (14)0.0100 (13)0.0039 (13)
C30.0451 (17)0.0345 (15)0.0367 (16)0.0023 (13)0.0103 (13)0.0092 (12)
C110.0297 (15)0.0428 (18)0.0539 (19)0.0021 (13)0.0005 (13)0.0075 (14)
C100.0324 (15)0.0479 (18)0.0379 (16)0.0053 (13)0.0053 (12)0.0078 (13)
C70.0516 (19)0.0360 (17)0.0434 (17)0.0142 (14)0.0037 (14)0.0042 (13)
C10.0342 (16)0.069 (2)0.0439 (19)0.0039 (16)0.0009 (13)0.0032 (16)
C20.0366 (17)0.058 (2)0.0508 (19)0.0073 (15)0.0113 (14)0.0118 (16)
C80.0372 (16)0.0372 (16)0.0362 (16)0.0054 (13)0.0002 (12)0.0018 (12)
C150.0474 (19)0.051 (2)0.054 (2)0.0050 (17)0.0056 (15)0.0021 (16)
C130.050 (2)0.092 (3)0.076 (3)0.016 (2)0.0239 (19)0.010 (2)
C120.050 (2)0.056 (2)0.073 (2)0.0045 (17)0.0194 (18)0.0051 (18)
C140.052 (2)0.080 (3)0.094 (3)0.007 (2)0.020 (2)0.037 (3)
O10.0653 (17)0.0819 (19)0.0602 (16)0.0233 (14)0.0070 (13)0.0333 (14)
O40.0422 (13)0.0675 (17)0.0849 (19)0.0155 (13)0.0160 (12)0.0061 (14)
O30.078 (2)0.0591 (18)0.095 (2)0.0009 (15)0.0306 (16)0.0207 (15)
C160.053 (3)0.112 (4)0.120 (4)0.013 (3)0.038 (3)0.003 (3)
C170.081 (4)0.197 (8)0.193 (7)0.074 (5)0.058 (4)0.069 (6)
Geometric parameters (Å, º) top
Br1—C31.870 (3)C7—C81.511 (4)
S1—C11.689 (3)C1—C21.345 (5)
S1—C41.736 (3)C1—H10.9300
C5—C61.339 (4)C2—H20.9300
C5—C41.452 (4)C8—C151.511 (4)
C5—C101.498 (4)C8—H80.9800
C4—C31.372 (4)C15—O31.188 (4)
C9—C111.488 (4)C15—O41.315 (4)
C9—C101.522 (4)C13—C141.306 (6)
C9—C81.524 (4)C13—C121.420 (5)
C9—H90.9800C13—H130.9300
O2—C111.357 (4)C12—H120.9300
O2—C141.362 (5)C14—H140.9300
C6—C71.442 (4)O4—C161.461 (5)
C6—H60.9300C16—C171.409 (7)
C3—C21.399 (4)C16—H16A0.9700
C11—C121.328 (5)C16—H16B0.9700
C10—H10A0.9700C17—H17A0.9600
C10—H10B0.9700C17—H17B0.9600
C7—O11.218 (4)C17—H17C0.9600
C1—S1—C492.98 (16)C1—C2—C3112.1 (3)
C6—C5—C4123.0 (3)C1—C2—H2123.9
C6—C5—C10119.3 (3)C3—C2—H2123.9
C4—C5—C10117.6 (2)C7—C8—C15107.9 (3)
C3—C4—C5133.8 (3)C7—C8—C9111.5 (2)
C3—C4—S1107.9 (2)C15—C8—C9111.6 (3)
C5—C4—S1118.4 (2)C7—C8—H8108.6
C11—C9—C10110.6 (2)C15—C8—H8108.6
C11—C9—C8111.1 (2)C9—C8—H8108.6
C10—C9—C8110.4 (2)O3—C15—O4124.5 (3)
C11—C9—H9108.2O3—C15—C8124.3 (3)
C10—C9—H9108.2O4—C15—C8111.2 (3)
C8—C9—H9108.2C14—C13—C12106.3 (4)
C11—O2—C14106.3 (3)C14—C13—H13126.9
C5—C6—C7123.6 (3)C12—C13—H13126.9
C5—C6—H6118.2C11—C12—C13107.1 (4)
C7—C6—H6118.2C11—C12—H12126.5
C4—C3—C2115.0 (3)C13—C12—H12126.5
C4—C3—Br1126.7 (2)C13—C14—O2110.9 (3)
C2—C3—Br1118.4 (2)C13—C14—H14124.5
C12—C11—O2109.5 (3)O2—C14—H14124.5
C12—C11—C9134.6 (3)C15—O4—C16116.6 (3)
O2—C11—C9115.8 (3)C17—C16—O4108.2 (4)
C5—C10—C9114.0 (2)C17—C16—H16A110.0
C5—C10—H10A108.8O4—C16—H16A110.0
C9—C10—H10A108.8C17—C16—H16B110.0
C5—C10—H10B108.8O4—C16—H16B110.0
C9—C10—H10B108.8H16A—C16—H16B108.4
H10A—C10—H10B107.7C16—C17—H17A109.5
O1—C7—C6120.9 (3)C16—C17—H17B109.5
O1—C7—C8120.1 (3)H17A—C17—H17B109.5
C6—C7—C8119.0 (3)C16—C17—H17C109.5
C2—C1—S1112.1 (2)H17A—C17—H17C109.5
C2—C1—H1124.0H17B—C17—H17C109.5
S1—C1—H1124.0
 

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