(8RS,9SR)-Ethyl 4-(3-bromo­thien-2-yl)-6-(2-fur­yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate

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.

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

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Computing details

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

Crystal data

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) Å^3	0.37 × 0.35 × 0.22 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.025P)^2 + 1.728P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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