

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808032650/kp2180sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808032650/kp2180Isup2.hkl |
CCDC reference: 709385
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean
(C-C) = 0.009 Å
- R factor = 0.067
- wR factor = 0.136
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.98 Ratio PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.84 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.54 Ratio PLAT360_ALERT_2_B Short C(sp3)-C(sp3) Bond C43 - C44 ... 1.33 Ang.
Alert level C ABSTY02_ALERT_1_C An _exptl_absorpt_correction_type has been given without a literature citation. This should be contained in the _exptl_absorpt_process_details field. Absorption correction given as numerical Value of measurement temperature given = 299.000 Value of melting point given = 0.000 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.76 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C43 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 9 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 2000 Deg.
Alert level G ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.613 0.881 Tmin and Tmax expected: 0.471 0.795 RR = 1.175 Please check that your absorption correction is appropriate. PLAT793_ALERT_4_G Check the Absolute Configuration of C8 ..... S PLAT793_ALERT_4_G Check the Absolute Configuration of C9 ..... R PLAT793_ALERT_4_G Check the Absolute Configuration of C29 ..... R PLAT793_ALERT_4_G Check the Absolute Configuration of C30 ..... S
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL023_ALERT_1_A There is a mismatched ^ on line 417 'calc w=1/[\s\^2^(Fo^2^)+5.8P] where P=(Fo^2^+2Fc^2^)/3' If you require a ^ then it should be escaped with a \, i.e. \^ Otherwise there must be a matching closing ~, e.g. ^12^C
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
(2E)-1-(3-Bromo-2-thienyl)-3-(4-propoxyphenyl)prop-2-en-1-one(1) (1.76 g, 5 mmol) and ethyl acetoacetate (2) (0.65 g, 5 mmol) were refluxed for 2 h in 15 mL ethanol in presence of 0.8 mL 10% NaOH. The reaction mixture was cooled to room temperature and the reaction mass was filtered and recrystallized using methanol. X-ray quality crystals were grown from acetone.Yield = 67%; mp 349–351 K. CHS Calculated: 57.02, 5.00, 6.92; Observed: 56.89,4.81, 6.80.
Hydrogen atoms were placed at calculated positions and refined riding on the respective carrier atom. Attempts to improve the structure model using a split position for C43 and C44 resulted in an unstable refinement. Attempts to acquire data at low temperature resulted in severe deterioration of the crystal quality.
Data collection: SMART (Bruker, 1998); cell refinement: DIRAX (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: please specify; software used to prepare material for publication: please specify.
![]() | Fig. 1. : The two molecules in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level. |
C22H23BrO4S | Z = 4 |
Mr = 463.40 | F(000) = 952 |
Triclinic, P1 | Dx = 1.464 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.809 (3) Å | Cell parameters from 26 reflections |
b = 11.878 (2) Å | θ = 5.7–16.4° |
c = 20.178 (7) Å | µ = 2.08 mm−1 |
α = 92.66 (2)° | T = 299 K |
β = 94.61 (2)° | Plate, colourless |
γ = 90.16 (2)° | 0.38 × 0.31 × 0.11 mm |
V = 2102.2 (11) Å3 |
Bruker–Nonius KappaCCD diffractometer | 4630 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.074 |
ϕ and ω scans | θmax = 25.5°, θmin = 4.6° |
Absorption correction: numerical (program? reference?) | h = −10→10 |
Tmin = 0.613, Tmax = 0.881 | k = −13→14 |
31851 measured reflections | l = −24→23 |
7652 independent reflections |
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)] = 0.067 | H-atom parameters constrained |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + 5.8P] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max = 0.001 |
7652 reflections | Δρmax = 0.45 e Å−3 |
506 parameters | Δρmin = −0.53 e Å−3 |
0 restraints |
C22H23BrO4S | γ = 90.16 (2)° |
Mr = 463.40 | V = 2102.2 (11) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.809 (3) Å | Mo Kα radiation |
b = 11.878 (2) Å | µ = 2.08 mm−1 |
c = 20.178 (7) Å | T = 299 K |
α = 92.66 (2)° | 0.38 × 0.31 × 0.11 mm |
β = 94.61 (2)° |
Bruker–Nonius KappaCCD diffractometer | 7652 independent reflections |
Absorption correction: numerical (program? reference?) | 4630 reflections with I > 2σ(I) |
Tmin = 0.613, Tmax = 0.881 | Rint = 0.074 |
31851 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.136 | H-atom parameters constrained |
S = 1.17 | Δρmax = 0.45 e Å−3 |
7652 reflections | Δρmin = −0.53 e Å−3 |
506 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 1.00872 (8) | 0.74502 (5) | 1.07626 (3) | 0.0570 (2) | |
Br2 | 0.51193 (8) | 0.76585 (5) | 1.07551 (3) | 0.0590 (2) | |
S1 | 0.69191 (18) | 0.46070 (13) | 1.03375 (8) | 0.0518 (4) | |
S2 | 0.19207 (18) | 1.04063 (14) | 1.03454 (8) | 0.0529 (4) | |
C1 | 0.7253 (7) | 0.4941 (5) | 1.1156 (3) | 0.0542 (16) | |
C2 | 0.8199 (7) | 0.5836 (5) | 1.1279 (3) | 0.0474 (14) | |
C3 | 0.8687 (6) | 0.6238 (4) | 1.0689 (3) | 0.0395 (13) | |
C4 | 0.8093 (6) | 0.5679 (4) | 1.0113 (3) | 0.0387 (13) | |
C5 | 0.8252 (6) | 0.5818 (4) | 0.9409 (3) | 0.0361 (12) | |
C6 | 0.9291 (7) | 0.6506 (4) | 0.9193 (3) | 0.0446 (14) | |
C7 | 0.9453 (7) | 0.6673 (4) | 0.8494 (3) | 0.0469 (14) | |
C8 | 0.8412 (6) | 0.6015 (4) | 0.7975 (3) | 0.0384 (12) | |
C9 | 0.7790 (6) | 0.4937 (4) | 0.8233 (3) | 0.0379 (12) | |
C10 | 0.7154 (6) | 0.5177 (4) | 0.8910 (3) | 0.0404 (13) | |
C11 | 0.6635 (6) | 0.4335 (4) | 0.7750 (3) | 0.0393 (13) | |
C12 | 0.5401 (7) | 0.4886 (5) | 0.7429 (3) | 0.0495 (15) | |
C13 | 0.4415 (8) | 0.4320 (5) | 0.6973 (3) | 0.0598 (17) | |
C14 | 0.4589 (7) | 0.3188 (5) | 0.6817 (3) | 0.0516 (15) | |
C15 | 0.5740 (7) | 0.2611 (5) | 0.7149 (3) | 0.0510 (15) | |
C16 | 0.6750 (7) | 0.3199 (4) | 0.7606 (3) | 0.0463 (14) | |
C17 | 0.3718 (9) | 0.1587 (6) | 0.6120 (4) | 0.072 (2) | |
C18 | 0.2557 (10) | 0.1339 (7) | 0.5533 (4) | 0.088 (3) | |
C19 | 0.2534 (13) | 0.0159 (9) | 0.5288 (6) | 0.144 (5) | |
C20 | 0.9318 (7) | 0.5792 (5) | 0.7381 (3) | 0.0495 (15) | |
C21 | 1.0231 (10) | 0.6541 (7) | 0.6429 (4) | 0.090 (3) | |
C22 | 0.9822 (14) | 0.7411 (8) | 0.5968 (5) | 0.136 (4) | |
C23 | 0.2240 (7) | 1.0186 (6) | 1.1170 (3) | 0.0553 (16) | |
C24 | 0.3224 (7) | 0.9319 (5) | 1.1279 (3) | 0.0495 (15) | |
C25 | 0.3712 (6) | 0.8839 (4) | 1.0692 (3) | 0.0399 (13) | |
C26 | 0.3119 (6) | 0.9313 (4) | 1.0117 (3) | 0.0376 (12) | |
C27 | 0.4301 (6) | 0.8377 (4) | 0.9187 (3) | 0.0450 (14) | |
C28 | 0.4458 (7) | 0.8132 (4) | 0.8486 (3) | 0.0478 (14) | |
C29 | 0.3417 (6) | 0.8698 (4) | 0.7973 (3) | 0.0399 (13) | |
C30 | 0.2803 (6) | 0.9815 (4) | 0.8246 (3) | 0.0396 (13) | |
C31 | 0.2186 (6) | 0.9668 (4) | 0.8918 (3) | 0.0412 (13) | |
C32 | 0.3274 (6) | 0.9096 (4) | 0.9413 (3) | 0.0386 (13) | |
C33 | 0.1648 (6) | 1.0349 (4) | 0.7757 (3) | 0.0395 (13) | |
C34 | 0.1797 (7) | 1.1466 (4) | 0.7618 (3) | 0.0457 (14) | |
C35 | 0.0795 (7) | 1.1981 (5) | 0.7162 (3) | 0.0513 (15) | |
C36 | −0.0374 (7) | 1.1362 (5) | 0.6834 (3) | 0.0477 (14) | |
C37 | −0.0588 (7) | 1.0261 (5) | 0.6991 (3) | 0.0561 (16) | |
C38 | 0.0409 (7) | 0.9759 (5) | 0.7438 (3) | 0.0505 (15) | |
C39 | −0.1223 (8) | 1.2903 (5) | 0.6170 (3) | 0.0592 (17) | |
C40 | −0.2396 (9) | 1.3122 (6) | 0.5615 (4) | 0.073 (2) | |
C41 | −0.2367 (12) | 1.4334 (7) | 0.5416 (5) | 0.112 (3) | |
C42 | 0.4294 (7) | 0.8853 (5) | 0.7374 (3) | 0.0518 (15) | |
C43 | 0.5140 (15) | 0.7996 (8) | 0.6391 (5) | 0.142 (5) | |
C44 | 0.5026 (15) | 0.7049 (9) | 0.6013 (5) | 0.146 (5) | |
O1 | 1.0389 (6) | 0.7333 (4) | 0.8325 (2) | 0.0744 (14) | |
O2 | 0.3581 (5) | 0.2734 (3) | 0.6319 (2) | 0.0654 (12) | |
O3 | 1.0136 (5) | 0.5001 (4) | 0.7321 (2) | 0.0650 (12) | |
O4 | 0.9151 (6) | 0.6605 (4) | 0.6946 (2) | 0.0655 (12) | |
O5 | 0.5407 (6) | 0.7450 (4) | 0.8317 (2) | 0.0753 (14) | |
O6 | −0.1381 (5) | 1.1766 (3) | 0.6339 (2) | 0.0608 (12) | |
O7 | 0.5113 (6) | 0.9633 (4) | 0.7307 (2) | 0.0740 (14) | |
O8 | 0.4101 (7) | 0.7991 (4) | 0.6931 (2) | 0.0820 (16) | |
H1 | 0.6832 | 0.4552 | 1.1487 | 0.065* | |
H2 | 0.8495 | 0.6145 | 1.1702 | 0.057* | |
H6 | 0.9947 | 0.6899 | 0.9506 | 0.054* | |
H8 | 0.7551 | 0.6497 | 0.7841 | 0.046* | |
H9 | 0.8651 | 0.4425 | 0.8306 | 0.046* | |
H10A | 0.6225 | 0.5609 | 0.8845 | 0.048* | |
H10B | 0.6893 | 0.4466 | 0.9092 | 0.048* | |
H12 | 0.5251 | 0.5648 | 0.7526 | 0.059* | |
H13 | 0.3610 | 0.4706 | 0.6764 | 0.072* | |
H15 | 0.5843 | 0.1838 | 0.7071 | 0.061* | |
H16 | 0.7535 | 0.2804 | 0.7825 | 0.056* | |
H17A | 0.3522 | 0.1114 | 0.6484 | 0.087* | |
H17B | 0.4738 | 0.1435 | 0.5992 | 0.087* | |
H18A | 0.1552 | 0.1540 | 0.5663 | 0.105* | |
H18B | 0.2782 | 0.1810 | 0.5173 | 0.105* | |
H19A | 0.3530 | −0.0052 | 0.5167 | 0.173* | |
H19B | 0.1815 | 0.0064 | 0.4906 | 0.173* | |
H19C | 0.2243 | −0.0310 | 0.5632 | 0.173* | |
H21A | 1.1263 | 0.6663 | 0.6625 | 0.108* | |
H21B | 1.0175 | 0.5805 | 0.6199 | 0.108* | |
H22A | 0.8867 | 0.7220 | 0.5726 | 0.163* | |
H22B | 1.0596 | 0.7469 | 0.5662 | 0.163* | |
H22C | 0.9733 | 0.8120 | 0.6210 | 0.163* | |
H23 | 0.1803 | 1.0609 | 1.1504 | 0.066* | |
H24 | 0.3530 | 0.9072 | 1.1699 | 0.059* | |
H27 | 0.4951 | 0.8018 | 0.9494 | 0.054* | |
H29 | 0.2553 | 0.8193 | 0.7840 | 0.048* | |
H30 | 0.3669 | 1.0337 | 0.8320 | 0.048* | |
H31A | 0.1253 | 0.9228 | 0.8851 | 0.049* | |
H31B | 0.1930 | 1.0404 | 0.9105 | 0.049* | |
H34 | 0.2591 | 1.1888 | 0.7837 | 0.055* | |
H35 | 0.0921 | 1.2737 | 0.7077 | 0.062* | |
H37 | −0.1420 | 0.9855 | 0.6791 | 0.067* | |
H38 | 0.0258 | 0.9009 | 0.7531 | 0.061* | |
H39A | −0.0211 | 1.3035 | 0.6032 | 0.071* | |
H39B | −0.1374 | 1.3404 | 0.6553 | 0.071* | |
H40A | −0.3397 | 1.2947 | 0.5751 | 0.088* | |
H40B | −0.2217 | 1.2628 | 0.5233 | 0.088* | |
H41A | −0.2348 | 1.4829 | 0.5806 | 0.135* | |
H41B | −0.3260 | 1.4480 | 0.5128 | 0.135* | |
H41C | −0.1475 | 1.4462 | 0.5185 | 0.135* | |
H43A | 0.4900 | 0.8631 | 0.6117 | 0.170* | |
H43B | 0.6181 | 0.8089 | 0.6583 | 0.170* | |
H44A | 0.5363 | 0.6427 | 0.6273 | 0.218* | |
H44B | 0.5648 | 0.7106 | 0.5646 | 0.218* | |
H44C | 0.3984 | 0.6928 | 0.5846 | 0.218* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0682 (5) | 0.0402 (3) | 0.0602 (4) | −0.0072 (3) | −0.0073 (3) | −0.0002 (3) |
Br2 | 0.0684 (5) | 0.0400 (3) | 0.0662 (5) | 0.0054 (3) | −0.0103 (3) | 0.0053 (3) |
S1 | 0.0468 (9) | 0.0620 (9) | 0.0474 (9) | −0.0140 (7) | 0.0051 (7) | 0.0089 (7) |
S2 | 0.0447 (9) | 0.0639 (10) | 0.0497 (10) | 0.0139 (7) | 0.0043 (7) | −0.0032 (7) |
C1 | 0.047 (4) | 0.072 (4) | 0.046 (4) | 0.001 (3) | 0.010 (3) | 0.018 (3) |
C2 | 0.045 (4) | 0.054 (3) | 0.043 (4) | 0.010 (3) | 0.002 (3) | 0.002 (3) |
C3 | 0.035 (3) | 0.036 (3) | 0.047 (3) | 0.009 (2) | −0.003 (3) | −0.002 (2) |
C4 | 0.034 (3) | 0.035 (3) | 0.049 (4) | 0.007 (2) | 0.007 (3) | 0.004 (2) |
C5 | 0.033 (3) | 0.030 (3) | 0.046 (3) | 0.007 (2) | 0.004 (2) | 0.004 (2) |
C6 | 0.049 (4) | 0.038 (3) | 0.046 (4) | −0.008 (3) | 0.003 (3) | −0.001 (3) |
C7 | 0.048 (4) | 0.032 (3) | 0.061 (4) | −0.002 (3) | 0.013 (3) | 0.003 (3) |
C8 | 0.040 (3) | 0.036 (3) | 0.041 (3) | 0.002 (2) | 0.010 (2) | 0.005 (2) |
C9 | 0.036 (3) | 0.035 (3) | 0.043 (3) | −0.001 (2) | 0.003 (2) | 0.006 (2) |
C10 | 0.038 (3) | 0.038 (3) | 0.046 (3) | −0.006 (2) | 0.005 (3) | 0.000 (2) |
C11 | 0.042 (3) | 0.037 (3) | 0.040 (3) | 0.000 (2) | 0.007 (3) | 0.005 (2) |
C12 | 0.056 (4) | 0.037 (3) | 0.055 (4) | 0.002 (3) | 0.002 (3) | 0.000 (3) |
C13 | 0.057 (4) | 0.052 (4) | 0.068 (5) | 0.000 (3) | −0.010 (3) | 0.004 (3) |
C14 | 0.056 (4) | 0.052 (4) | 0.046 (4) | −0.009 (3) | 0.004 (3) | −0.005 (3) |
C15 | 0.063 (4) | 0.035 (3) | 0.056 (4) | −0.001 (3) | 0.008 (3) | 0.003 (3) |
C16 | 0.048 (4) | 0.039 (3) | 0.052 (4) | −0.002 (3) | 0.001 (3) | 0.005 (3) |
C17 | 0.085 (5) | 0.066 (4) | 0.065 (5) | −0.022 (4) | 0.005 (4) | −0.015 (4) |
C18 | 0.100 (6) | 0.093 (6) | 0.065 (5) | −0.023 (5) | −0.009 (4) | −0.021 (4) |
C19 | 0.134 (10) | 0.129 (9) | 0.156 (11) | −0.018 (7) | −0.031 (8) | −0.064 (8) |
C20 | 0.057 (4) | 0.044 (3) | 0.048 (4) | −0.008 (3) | 0.005 (3) | 0.004 (3) |
C21 | 0.113 (7) | 0.106 (6) | 0.057 (5) | −0.006 (5) | 0.039 (5) | 0.012 (4) |
C22 | 0.208 (13) | 0.123 (8) | 0.088 (7) | 0.016 (8) | 0.070 (8) | 0.040 (6) |
C23 | 0.040 (4) | 0.075 (4) | 0.049 (4) | −0.004 (3) | 0.005 (3) | −0.012 (3) |
C24 | 0.040 (3) | 0.059 (4) | 0.049 (4) | −0.019 (3) | −0.003 (3) | 0.004 (3) |
C25 | 0.039 (3) | 0.036 (3) | 0.044 (3) | −0.015 (2) | −0.003 (3) | 0.001 (2) |
C26 | 0.024 (3) | 0.038 (3) | 0.051 (4) | −0.009 (2) | 0.001 (2) | −0.004 (2) |
C27 | 0.039 (3) | 0.039 (3) | 0.056 (4) | 0.005 (3) | 0.000 (3) | 0.004 (3) |
C28 | 0.051 (4) | 0.036 (3) | 0.057 (4) | −0.001 (3) | 0.008 (3) | −0.003 (3) |
C29 | 0.039 (3) | 0.034 (3) | 0.047 (3) | −0.001 (2) | 0.007 (3) | −0.001 (2) |
C30 | 0.037 (3) | 0.033 (3) | 0.049 (3) | −0.004 (2) | 0.003 (3) | −0.001 (2) |
C31 | 0.044 (3) | 0.035 (3) | 0.044 (3) | 0.008 (2) | 0.004 (3) | −0.002 (2) |
C32 | 0.033 (3) | 0.030 (3) | 0.051 (4) | −0.008 (2) | 0.001 (3) | 0.001 (2) |
C33 | 0.044 (3) | 0.034 (3) | 0.041 (3) | 0.000 (2) | 0.009 (3) | 0.000 (2) |
C34 | 0.047 (4) | 0.036 (3) | 0.053 (4) | −0.004 (3) | −0.003 (3) | 0.001 (3) |
C35 | 0.061 (4) | 0.036 (3) | 0.056 (4) | 0.001 (3) | 0.002 (3) | 0.003 (3) |
C36 | 0.052 (4) | 0.050 (3) | 0.041 (3) | 0.003 (3) | 0.002 (3) | 0.004 (3) |
C37 | 0.056 (4) | 0.051 (4) | 0.059 (4) | −0.012 (3) | −0.012 (3) | 0.005 (3) |
C38 | 0.050 (4) | 0.036 (3) | 0.066 (4) | −0.003 (3) | 0.002 (3) | 0.010 (3) |
C39 | 0.069 (5) | 0.061 (4) | 0.048 (4) | 0.013 (3) | 0.003 (3) | 0.008 (3) |
C40 | 0.089 (6) | 0.076 (5) | 0.055 (4) | 0.015 (4) | 0.000 (4) | 0.011 (4) |
C41 | 0.146 (9) | 0.085 (6) | 0.101 (7) | 0.021 (6) | −0.030 (6) | 0.025 (5) |
C42 | 0.055 (4) | 0.047 (3) | 0.055 (4) | 0.009 (3) | 0.014 (3) | −0.001 (3) |
C43 | 0.253 (14) | 0.097 (7) | 0.087 (7) | −0.033 (8) | 0.105 (8) | −0.031 (6) |
C44 | 0.207 (13) | 0.126 (9) | 0.114 (9) | 0.013 (9) | 0.083 (9) | −0.009 (7) |
O1 | 0.094 (4) | 0.073 (3) | 0.058 (3) | −0.044 (3) | 0.013 (3) | 0.008 (2) |
O2 | 0.075 (3) | 0.056 (3) | 0.062 (3) | −0.015 (2) | −0.014 (2) | −0.003 (2) |
O3 | 0.073 (3) | 0.059 (3) | 0.066 (3) | 0.016 (2) | 0.024 (2) | 0.002 (2) |
O4 | 0.088 (4) | 0.065 (3) | 0.048 (3) | 0.008 (2) | 0.022 (2) | 0.018 (2) |
O5 | 0.087 (4) | 0.066 (3) | 0.075 (3) | 0.037 (3) | 0.017 (3) | −0.006 (2) |
O6 | 0.071 (3) | 0.053 (2) | 0.057 (3) | 0.003 (2) | −0.010 (2) | 0.009 (2) |
O7 | 0.082 (4) | 0.063 (3) | 0.082 (4) | −0.019 (3) | 0.034 (3) | 0.006 (2) |
O8 | 0.125 (5) | 0.062 (3) | 0.062 (3) | −0.008 (3) | 0.038 (3) | −0.014 (2) |
Br1—C3 | 1.887 (5) | C39—O6 | 1.418 (7) |
Br2—C25 | 1.877 (6) | C39—C40 | 1.495 (9) |
S1—C1 | 1.682 (6) | C40—C41 | 1.513 (10) |
S1—C4 | 1.737 (5) | C42—O7 | 1.192 (7) |
S2—C23 | 1.697 (7) | C42—O8 | 1.329 (7) |
S2—C26 | 1.744 (5) | C43—C44 | 1.329 (12) |
C1—C2 | 1.350 (8) | C43—O8 | 1.480 (9) |
C2—C3 | 1.402 (8) | C1—H1 | 0.9300 |
C3—C4 | 1.375 (7) | C2—H2 | 0.9301 |
C4—C5 | 1.456 (7) | C6—H6 | 0.9300 |
C5—C6 | 1.338 (7) | C8—H8 | 0.9800 |
C5—C10 | 1.516 (7) | C9—H9 | 0.9800 |
C6—C7 | 1.451 (8) | C10—H10A | 0.9700 |
C7—O1 | 1.216 (6) | C10—H10B | 0.9700 |
C7—C8 | 1.521 (8) | C12—H12 | 0.9299 |
C8—C20 | 1.507 (8) | C13—H13 | 0.9301 |
C8—C9 | 1.522 (7) | C15—H15 | 0.9300 |
C9—C11 | 1.506 (7) | C16—H16 | 0.9300 |
C9—C10 | 1.533 (7) | C17—H17A | 0.9699 |
C11—C16 | 1.372 (7) | C17—H17B | 0.9700 |
C11—C12 | 1.400 (8) | C18—H18A | 0.9700 |
C12—C13 | 1.364 (8) | C18—H18B | 0.9700 |
C13—C14 | 1.378 (8) | C19—H19A | 0.9600 |
C14—C15 | 1.373 (8) | C19—H19B | 0.9600 |
C14—O2 | 1.376 (7) | C19—H19C | 0.9600 |
C15—C16 | 1.391 (8) | C21—H21A | 0.9700 |
C17—O2 | 1.411 (7) | C21—H21B | 0.9700 |
C17—C18 | 1.518 (9) | C22—H22A | 0.9600 |
C18—C19 | 1.464 (11) | C22—H22B | 0.9599 |
C20—O3 | 1.193 (7) | C22—H22C | 0.9601 |
C20—O4 | 1.335 (7) | C23—H23 | 0.9300 |
C21—C22 | 1.449 (11) | C24—H24 | 0.9299 |
C21—O4 | 1.467 (8) | C27—H27 | 0.9301 |
C23—C24 | 1.363 (8) | C29—H29 | 0.9800 |
C24—C25 | 1.390 (8) | C30—H30 | 0.9800 |
C25—C26 | 1.378 (7) | C31—H31A | 0.9700 |
C26—C32 | 1.450 (7) | C31—H31B | 0.9700 |
C27—C32 | 1.338 (7) | C34—H34 | 0.9300 |
C27—C28 | 1.448 (8) | C35—H35 | 0.9299 |
C28—O5 | 1.223 (7) | C37—H37 | 0.9300 |
C28—C29 | 1.510 (8) | C38—H38 | 0.9300 |
C29—C42 | 1.503 (8) | C39—H39A | 0.9700 |
C29—C30 | 1.530 (7) | C39—H39B | 0.9701 |
C30—C31 | 1.519 (7) | C40—H40A | 0.9700 |
C30—C33 | 1.519 (7) | C40—H40B | 0.9700 |
C31—C32 | 1.514 (7) | C41—H41A | 0.9600 |
C33—C34 | 1.376 (7) | C41—H41B | 0.9601 |
C33—C38 | 1.393 (8) | C41—H41C | 0.9600 |
C34—C35 | 1.386 (8) | C43—H43A | 0.9700 |
C35—C36 | 1.371 (8) | C43—H43B | 0.9700 |
C36—C37 | 1.376 (8) | C44—H44A | 0.9600 |
C36—O6 | 1.385 (7) | C44—H44B | 0.9600 |
C37—C38 | 1.366 (8) | C44—H44C | 0.9600 |
C1—S1—C4 | 93.0 (3) | C10—C9—H9 | 107.0 |
C23—S2—C26 | 93.2 (3) | C5—C10—H10A | 108.8 |
C2—C1—S1 | 112.6 (5) | C9—C10—H10A | 108.8 |
C1—C2—C3 | 111.4 (5) | C5—C10—H10B | 108.9 |
C4—C3—C2 | 115.2 (5) | C9—C10—H10B | 108.8 |
C4—C3—Br1 | 127.1 (4) | H10A—C10—H10B | 107.7 |
C2—C3—Br1 | 117.6 (4) | C13—C12—H12 | 119.4 |
C3—C4—C5 | 133.8 (5) | C11—C12—H12 | 119.6 |
C3—C4—S1 | 107.7 (4) | C12—C13—H13 | 119.3 |
C5—C4—S1 | 118.5 (4) | C14—C13—H13 | 119.3 |
C6—C5—C4 | 122.6 (5) | C14—C15—H15 | 120.6 |
C6—C5—C10 | 119.6 (5) | C16—C15—H15 | 120.4 |
C4—C5—C10 | 117.8 (5) | C11—C16—H16 | 118.6 |
C5—C6—C7 | 123.6 (5) | C15—C16—H16 | 118.5 |
O1—C7—C6 | 120.9 (5) | O2—C17—H17A | 110.1 |
O1—C7—C8 | 120.4 (5) | C18—C17—H17A | 110.1 |
C6—C7—C8 | 118.7 (5) | O2—C17—H17B | 110.2 |
C20—C8—C7 | 106.6 (5) | C18—C17—H17B | 110.3 |
C20—C8—C9 | 112.3 (4) | H17A—C17—H17B | 108.5 |
C7—C8—C9 | 112.9 (4) | C19—C18—H18A | 109.0 |
C11—C9—C8 | 113.7 (4) | C17—C18—H18A | 108.9 |
C11—C9—C10 | 111.4 (4) | C19—C18—H18B | 108.7 |
C8—C9—C10 | 110.3 (4) | C17—C18—H18B | 108.8 |
C5—C10—C9 | 113.6 (4) | H18A—C18—H18B | 107.7 |
C16—C11—C12 | 116.6 (5) | C18—C19—H19A | 109.6 |
C16—C11—C9 | 120.7 (5) | C18—C19—H19B | 109.5 |
C12—C11—C9 | 122.7 (5) | H19A—C19—H19B | 109.5 |
C13—C12—C11 | 120.9 (5) | C18—C19—H19C | 109.3 |
C12—C13—C14 | 121.4 (6) | H19A—C19—H19C | 109.5 |
C15—C14—O2 | 125.2 (5) | H19B—C19—H19C | 109.5 |
C15—C14—C13 | 119.1 (6) | C22—C21—H21A | 110.1 |
O2—C14—C13 | 115.7 (6) | O4—C21—H21A | 110.3 |
C14—C15—C16 | 119.0 (5) | C22—C21—H21B | 110.3 |
C11—C16—C15 | 122.9 (5) | O4—C21—H21B | 110.2 |
O2—C17—C18 | 107.6 (6) | H21A—C21—H21B | 108.5 |
C19—C18—C17 | 113.6 (8) | C21—C22—H22A | 109.4 |
O3—C20—O4 | 124.1 (6) | C21—C22—H22B | 109.5 |
O3—C20—C8 | 123.6 (5) | H22A—C22—H22B | 109.5 |
O4—C20—C8 | 112.3 (5) | C21—C22—H22C | 109.5 |
C22—C21—O4 | 107.4 (7) | H22A—C22—H22C | 109.5 |
C24—C23—S2 | 111.3 (5) | H22B—C22—H22C | 109.5 |
C23—C24—C25 | 112.6 (6) | C24—C23—H23 | 124.5 |
C26—C25—C24 | 115.3 (5) | S2—C23—H23 | 124.2 |
C26—C25—Br2 | 126.7 (4) | C23—C24—H24 | 123.7 |
C24—C25—Br2 | 118.0 (4) | C25—C24—H24 | 123.7 |
C25—C26—C32 | 134.8 (5) | C32—C27—H27 | 118.4 |
C25—C26—S2 | 107.7 (4) | C28—C27—H27 | 118.2 |
C32—C26—S2 | 117.5 (4) | C42—C29—H29 | 108.3 |
C32—C27—C28 | 123.4 (5) | C28—C29—H29 | 108.4 |
O5—C28—C27 | 119.7 (6) | C30—C29—H29 | 108.5 |
O5—C28—C29 | 120.8 (6) | C31—C30—H30 | 106.9 |
C27—C28—C29 | 119.5 (5) | C33—C30—H30 | 106.9 |
C42—C29—C28 | 107.6 (5) | C29—C30—H30 | 107.0 |
C42—C29—C30 | 111.9 (4) | C32—C31—H31A | 108.7 |
C28—C29—C30 | 112.0 (5) | C30—C31—H31A | 108.6 |
C31—C30—C33 | 112.3 (4) | C32—C31—H31B | 108.9 |
C31—C30—C29 | 110.5 (4) | C30—C31—H31B | 108.7 |
C33—C30—C29 | 112.8 (4) | H31A—C31—H31B | 107.6 |
C32—C31—C30 | 114.2 (5) | C33—C34—H34 | 119.0 |
C27—C32—C26 | 122.5 (5) | C35—C34—H34 | 119.0 |
C27—C32—C31 | 119.0 (5) | C36—C35—H35 | 120.3 |
C26—C32—C31 | 118.5 (5) | C34—C35—H35 | 120.3 |
C34—C33—C38 | 117.2 (5) | C38—C37—H37 | 119.7 |
C34—C33—C30 | 120.0 (5) | C36—C37—H37 | 119.7 |
C38—C33—C30 | 122.8 (5) | C37—C38—H38 | 119.4 |
C33—C34—C35 | 122.0 (5) | C33—C38—H38 | 119.4 |
C36—C35—C34 | 119.4 (5) | O6—C39—H39A | 110.2 |
C35—C36—C37 | 119.5 (6) | C40—C39—H39A | 110.2 |
C35—C36—O6 | 124.4 (5) | O6—C39—H39B | 110.0 |
C37—C36—O6 | 116.1 (5) | C40—C39—H39B | 110.1 |
C38—C37—C36 | 120.7 (6) | H39A—C39—H39B | 108.5 |
C37—C38—C33 | 121.2 (5) | C39—C40—H40A | 109.2 |
O6—C39—C40 | 107.9 (5) | C41—C40—H40A | 109.1 |
C39—C40—C41 | 112.1 (7) | C39—C40—H40B | 109.1 |
O7—C42—O8 | 123.2 (6) | C41—C40—H40B | 109.3 |
O7—C42—C29 | 124.7 (6) | H40A—C40—H40B | 107.9 |
O8—C42—C29 | 112.1 (5) | C40—C41—H41A | 109.6 |
C44—C43—O8 | 111.6 (9) | C40—C41—H41B | 109.4 |
C14—O2—C17 | 118.9 (5) | H41A—C41—H41B | 109.5 |
C20—O4—C21 | 114.1 (5) | C40—C41—H41C | 109.4 |
C36—O6—C39 | 118.1 (5) | H41A—C41—H41C | 109.5 |
C42—O8—C43 | 114.5 (6) | H41B—C41—H41C | 109.5 |
C2—C1—H1 | 123.7 | C44—C43—H43A | 109.3 |
S1—C1—H1 | 123.7 | O8—C43—H43A | 109.3 |
C1—C2—H2 | 124.4 | C44—C43—H43B | 109.3 |
C3—C2—H2 | 124.2 | O8—C43—H43B | 109.3 |
C5—C6—H6 | 118.3 | H43A—C43—H43B | 108.0 |
C7—C6—H6 | 118.1 | C43—C44—H44A | 109.5 |
C20—C8—H8 | 108.2 | C43—C44—H44B | 109.5 |
C7—C8—H8 | 108.2 | H44A—C44—H44B | 109.5 |
C9—C8—H8 | 108.4 | C43—C44—H44C | 109.5 |
C11—C9—H9 | 107.0 | H44A—C44—H44C | 109.5 |
C8—C9—H9 | 107.1 | H44B—C44—H44C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C22H23BrO4S |
Mr | 463.40 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 299 |
a, b, c (Å) | 8.809 (3), 11.878 (2), 20.178 (7) |
α, β, γ (°) | 92.66 (2), 94.61 (2), 90.16 (2) |
V (Å3) | 2102.2 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.08 |
Crystal size (mm) | 0.38 × 0.31 × 0.11 |
Data collection | |
Diffractometer | Bruker–Nonius KappaCCD diffractometer |
Absorption correction | Numerical (program? reference?) |
Tmin, Tmax | 0.613, 0.881 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31851, 7652, 4630 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.136, 1.17 |
No. of reflections | 7652 |
No. of parameters | 506 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.53 |
Computer programs: SMART (Bruker, 1998), DIRAX (Duisenberg, 1992), EVALCCD (Duisenberg et al., 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), please specify.
Chalcones and the corresponding heterocyclic analogues are valuable intermediates in organic synthesis (Dhar, 1981) and exhibit a multitude of biological activities (Dimmock et al. 1999). From a chemical point of view, an important feature of chalcones and their heteroanalogues is the ability to act as activated unsaturated systems in conjugated addition reactions of carbanions in the presence of basic catalysts (House, 1972). This type of reaction may be exploited with the view of obtaining highly functionalized cyclohexene derivatives (Tabba et al.,1995) but is more commonly used for the preparation of 3,5-diaryl-6-carbethoxycyclohexanones via Michael addition of ethylacetoacetate. The mentioned cyclohexenones are efficient synthons in building spiranic compounds (Padmavathi et al.,2001) or intermediates in the synthesis of benzisoxazoles or carbazolederivatives (Padmavathi et al., 1999, 2000, 2001a,b). In view of the importance of these derivatives, a new derivative rac-ethyl-3-(3-bromo-2-thienyl)-6-(4-propoxyphenyl)-2-oxocyclohex-3-ene-1-carboxylate, C22H23BrO4S was prepared and the crystal structure is reported here.
The compound is prepared by the cyclocondensation of ethyl acetoacetate with chalcone which leads to the generation of two chiral centers at C1 and C6 in the structure of cyclohexanone (I). As the reaction is not stereoselective, both configurations of the chiral carbon atoms are expected to be obtained in the synthesiszed cyclohexanone(I), which would result in a mixture of diastereomers. No attempt to separate the diastereomeric I has been undertaken and the crystals were grown from the mixture after recrystallization.