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The title compound, C21H18O2S, was synthesized by the reaction of thio­phene-2-carbaldehyde with acetophenone and NaOH. All bond lengths and angles show normal values. The crystal packing is stabilized by weak inter­molecular C—H...O hydrogen bonds and van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032429/cv2102sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032429/cv2102Isup2.hkl
Contains datablock I

CCDC reference: 620952

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.061
  • wR factor = 0.200
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 1747.00 Ang-3 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C1 - C2 ... 1.31 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 14.90 Deg. C3' -C1 -S1 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 11.20 Deg. C3 -C2 -S1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 9.40 Deg. C3 -C4 -S1' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 13.60 Deg. C3' -C4 -S1 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,5-Diphenyl-3-(2-thienyl)pentane-1,5-dione top
Crystal data top
C21H18O2SF(000) = 704
Mr = 334.41Dx = 1.272 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.460 (2) ÅCell parameters from 2006 reflections
b = 12.094 (3) Åθ = 2.3–20.7°
c = 10.762 (2) ŵ = 0.20 mm1
β = 94.456 (3)°T = 298 K
V = 1746.6 (6) Å3Block, colourless
Z = 40.58 × 0.55 × 0.53 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3061 independent reflections
Radiation source: fine-focus sealed tube1620 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1316
Tmin = 0.896, Tmax = 0.904k = 1214
8511 measured reflectionsl = 129
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.200H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0999P)2 + 0.3043P]
where P = (Fo2 + 2Fc2)/3
3061 reflections(Δ/σ)max < 0.001
224 parametersΔρmax = 0.23 e Å3
11 restraintsΔρmin = 0.31 e Å3
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*/UeqOcc. (<1)
O10.1375 (2)0.8000 (2)1.1690 (2)0.0923 (9)
O20.39329 (19)0.89264 (19)0.9624 (2)0.0806 (8)
S10.29544 (15)0.51245 (15)1.13483 (15)0.0957 (8)0.735 (5)
C3'0.2666 (14)0.5095 (13)1.1086 (15)0.0957 (8)0.265 (5)
H3'0.32290.52001.16310.115*0.265 (5)
C10.2206 (5)0.4085 (4)1.1064 (4)0.1055 (16)
H10.22890.34101.14720.127*
C20.1465 (4)0.4283 (4)1.0232 (5)0.1000 (15)
H20.09700.37780.99750.120*
C30.1521 (10)0.5387 (11)0.9813 (13)0.090 (2)0.735 (5)
H30.10490.56920.92360.108*0.735 (5)
S1'0.1344 (7)0.5462 (8)0.9584 (9)0.090 (2)0.265 (5)
C40.2327 (2)0.5975 (2)1.0325 (3)0.0543 (8)
C50.2699 (2)0.7117 (2)1.0089 (3)0.0513 (8)
H50.30090.74111.08750.062*
C60.1849 (2)0.7882 (3)0.9638 (3)0.0579 (9)
H6A0.21260.85840.93990.069*
H6B0.15010.75630.89010.069*
C70.1119 (3)0.8088 (3)1.0586 (3)0.0568 (8)
C80.0097 (2)0.8429 (2)1.0181 (3)0.0508 (8)
C90.0249 (3)0.8522 (3)0.8944 (3)0.0624 (9)
H90.01770.83670.83260.075*
C100.1211 (3)0.8840 (3)0.8616 (4)0.0775 (11)
H100.14360.89000.77800.093*
C110.1836 (3)0.9068 (3)0.9517 (4)0.0823 (11)
H110.24910.92780.92980.099*
C120.1503 (3)0.8989 (3)1.0740 (4)0.0827 (12)
H120.19300.91521.13530.099*
C130.0556 (3)0.8674 (3)1.1071 (3)0.0673 (9)
H130.03410.86211.19110.081*
C140.3489 (2)0.7060 (2)0.9158 (3)0.0537 (8)
H14A0.39480.64680.94070.064*
H14B0.31660.68660.83510.064*
C150.4082 (2)0.8102 (3)0.9014 (3)0.0569 (8)
C160.4863 (2)0.8089 (3)0.8129 (3)0.0558 (8)
C170.5054 (3)0.7176 (3)0.7414 (3)0.0752 (10)
H170.46820.65360.74980.090*
C180.5775 (3)0.7187 (4)0.6589 (4)0.0927 (13)
H180.58960.65560.61290.111*
C190.6311 (3)0.8115 (6)0.6439 (5)0.1048 (16)
H190.67930.81330.58640.126*
C200.6141 (3)0.9026 (5)0.7140 (6)0.1100 (17)
H200.65170.96610.70440.132*
C210.5425 (3)0.9026 (3)0.7984 (4)0.0840 (12)
H210.53210.96550.84540.101*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.112 (2)0.128 (2)0.0370 (14)0.0434 (17)0.0073 (13)0.0004 (13)
O20.0933 (19)0.0533 (15)0.0957 (19)0.0151 (13)0.0101 (14)0.0190 (13)
S10.1474 (18)0.0681 (9)0.0675 (11)0.0232 (9)0.0183 (9)0.0176 (7)
C3'0.1474 (18)0.0681 (9)0.0675 (11)0.0232 (9)0.0183 (9)0.0176 (7)
C10.172 (5)0.068 (3)0.082 (3)0.025 (3)0.045 (3)0.001 (2)
C20.095 (3)0.078 (3)0.133 (4)0.038 (3)0.044 (3)0.031 (3)
C30.083 (4)0.071 (2)0.111 (4)0.010 (2)0.020 (3)0.000 (2)
S1'0.083 (4)0.071 (2)0.111 (4)0.010 (2)0.020 (3)0.000 (2)
C40.065 (2)0.0533 (18)0.0470 (17)0.0065 (15)0.0185 (15)0.0040 (14)
C50.062 (2)0.0499 (18)0.0415 (17)0.0037 (14)0.0031 (14)0.0021 (13)
C60.068 (2)0.065 (2)0.0415 (17)0.0071 (16)0.0069 (15)0.0012 (15)
C70.078 (2)0.0557 (19)0.0372 (18)0.0091 (16)0.0084 (16)0.0007 (14)
C80.067 (2)0.0434 (17)0.0430 (18)0.0031 (14)0.0135 (16)0.0005 (13)
C90.067 (2)0.066 (2)0.055 (2)0.0013 (17)0.0111 (17)0.0007 (16)
C100.074 (3)0.091 (3)0.067 (2)0.001 (2)0.001 (2)0.004 (2)
C110.064 (2)0.082 (3)0.101 (3)0.003 (2)0.007 (2)0.002 (2)
C120.078 (3)0.084 (3)0.090 (3)0.003 (2)0.033 (2)0.005 (2)
C130.078 (3)0.069 (2)0.057 (2)0.0025 (19)0.0186 (19)0.0003 (17)
C140.059 (2)0.0479 (18)0.0548 (19)0.0064 (14)0.0068 (15)0.0018 (14)
C150.061 (2)0.0490 (19)0.059 (2)0.0045 (15)0.0055 (17)0.0025 (16)
C160.054 (2)0.0545 (19)0.057 (2)0.0060 (15)0.0037 (16)0.0119 (16)
C170.065 (2)0.090 (3)0.072 (2)0.020 (2)0.0165 (19)0.005 (2)
C180.066 (3)0.133 (4)0.080 (3)0.012 (3)0.014 (2)0.008 (3)
C190.075 (3)0.149 (5)0.092 (3)0.004 (3)0.017 (2)0.045 (3)
C200.079 (3)0.105 (4)0.148 (5)0.012 (3)0.019 (3)0.067 (4)
C210.073 (3)0.063 (2)0.117 (3)0.0070 (19)0.007 (2)0.031 (2)
Geometric parameters (Å, º) top
O1—C71.216 (4)C9—C101.371 (5)
O2—C151.219 (4)C9—H90.9300
S1—C11.625 (6)C10—C111.361 (5)
S1—C41.685 (4)C10—H100.9300
C3'—C11.368 (17)C11—C121.360 (6)
C3'—C41.398 (16)C11—H110.9300
C3'—H3'0.9300C12—C131.351 (6)
C1—C21.310 (6)C12—H120.9300
C1—H10.9300C13—H130.9300
C2—C31.413 (14)C14—C151.506 (5)
C2—S1'1.591 (12)C14—H14A0.9700
C2—H20.9300C14—H14B0.9700
C3—C41.376 (13)C15—C161.473 (5)
C3—H30.9300C16—C211.379 (5)
S1'—C41.615 (11)C16—C171.381 (5)
C4—C51.498 (5)C17—C181.365 (6)
C5—C141.517 (5)C17—H170.9300
C5—C61.522 (5)C18—C191.351 (7)
C5—H50.9800C18—H180.9300
C6—C71.492 (5)C19—C201.365 (7)
C6—H6A0.9700C19—H190.9300
C6—H6B0.9700C20—C211.374 (6)
C7—C81.469 (5)C20—H200.9300
C8—C91.380 (5)C21—H210.9300
C8—C131.381 (5)
C1—S1—C494.4 (3)C9—C8—C13117.8 (3)
C1—C3'—C4122.9 (15)C9—C8—C7123.1 (3)
C1—C3'—H3'118.6C13—C8—C7119.1 (3)
C4—C3'—H3'118.6C10—C9—C8120.8 (3)
C2—C1—C3'99.7 (9)C10—C9—H9119.6
C2—C1—S1114.6 (4)C8—C9—H9119.6
C3'—C1—S114.9 (8)C11—C10—C9119.8 (4)
C2—C1—H1122.7C11—C10—H10120.1
C3'—C1—H1137.5C9—C10—H10120.1
S1—C1—H1122.7C12—C11—C10120.0 (4)
C1—C2—C3109.5 (7)C12—C11—H11120.0
C1—C2—S1'120.6 (5)C10—C11—H11120.0
C3—C2—S1'11.2 (9)C13—C12—C11120.6 (4)
C1—C2—H2125.0C13—C12—H12119.7
C3—C2—H2125.5C11—C12—H12119.7
S1'—C2—H2114.4C12—C13—C8121.0 (4)
C4—C3—C2114.9 (11)C12—C13—H13119.5
C4—C3—H3122.5C8—C13—H13119.5
C2—C3—H3122.5C15—C14—C5115.7 (3)
C2—S1'—C494.4 (6)C15—C14—H14A108.3
C3—C4—C3'93.0 (11)C5—C14—H14A108.3
C3—C4—C5132.3 (7)C15—C14—H14B108.3
C3'—C4—C5134.7 (9)C5—C14—H14B108.3
C3—C4—S1'9.4 (10)H14A—C14—H14B107.4
C3'—C4—S1'102.4 (9)O2—C15—C16120.8 (3)
C5—C4—S1'122.9 (4)O2—C15—C14121.2 (3)
C3—C4—S1106.6 (7)C16—C15—C14117.9 (3)
C3'—C4—S113.6 (8)C21—C16—C17117.8 (4)
C5—C4—S1121.1 (3)C21—C16—C15119.3 (3)
S1'—C4—S1116.0 (4)C17—C16—C15122.8 (3)
C4—C5—C14109.3 (2)C18—C17—C16121.8 (4)
C4—C5—C6111.2 (3)C18—C17—H17119.1
C14—C5—C6111.4 (3)C16—C17—H17119.1
C4—C5—H5108.3C19—C18—C17119.9 (5)
C14—C5—H5108.3C19—C18—H18120.0
C6—C5—H5108.3C17—C18—H18120.0
C7—C6—C5113.8 (3)C18—C19—C20119.4 (5)
C7—C6—H6A108.8C18—C19—H19120.3
C5—C6—H6A108.8C20—C19—H19120.3
C7—C6—H6B108.8C19—C20—C21121.5 (4)
C5—C6—H6B108.8C19—C20—H20119.3
H6A—C6—H6B107.7C21—C20—H20119.3
O1—C7—C8120.1 (3)C20—C21—C16119.6 (4)
O1—C7—C6120.1 (3)C20—C21—H21120.2
C8—C7—C6119.7 (3)C16—C21—H21120.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···O1i0.972.473.361 (7)153
Symmetry code: (i) x, y+3/2, z1/2.
 

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