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The experimental and theoretical charge densities of 1,4-bis(5-hexyl-2-thienyl)butane-1,4-dione, a precursor in the synthesis of thiophene-based semiconductors and organic solar cells, are presented. A dummy bond charges spherical atom model is applied besides the multipolar atom model. The results show that the dummy bond charges model is accurate enough to calculate electrostatic-derived properties which are comparable with those obtained by the multipolar atom model. The refinement statistics and the residual electron density values are found to be intermediate between the independent atom and the multipolar formalisms.

Supporting information

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615019083/gw5041sup3.pdf
Fourier spherical residual map. XDRK plots of diffraction data. Laplacian maps. Electron Density and Laplacian at bond critical point with EXP_MUL and THEO_MUL_Kcore models. Topology of intermolecular contacts.

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615019083/gw5041sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615019083/gw5041Isup2.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615019083/gw5041sup3.pdf
Supplementary material

CCDC reference: 1430523

Computing details top

Program(s) used to refine structure: MoPro (J. Appl. Cryst. 2005, 38, 38-54).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
1,4-bis (5-hexyl-2-thienyl) butane-1,4 dione top
Crystal data top
C24H34O2S2γ = 95.39 (15)°
Mr = 418.63V = 564.4 (9) Å3
Triclinic, P1Z = 1
Hall symbol: -P 1F(000) = 226
a = 5.047 (5) ÅDx = 1.232 Mg m3
b = 6.979 (6) ÅMo Kα radiation, λ = 0.71073 Å
c = 16.333 (9) ÅT = 100 K
α = 98.79 (16)°Rectangular block, yellow
β = 93.52 (15)°0.43 × 0.14 × 0.08 mm
Data collection top
Four-circle
diffractometer
Rint = 0.053
Radiation source: fine-focus sealed tubeθmax = 46.9°, θmin = 3.4°
ω scansh = 010
70042 measured reflectionsk = 1414
9170 independent reflectionsl = 3333
9170 reflections with > 2.0σ(I)
Refinement top
Refinement on F2342 restraints
Least-squares matrix: fullPrimary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.043Secondary atom site location: difference Fourier map
wR(F2) = 0.072Hydrogen site location: difference Fourier map
S = 1.05Only H-atom coordinates refined
9169 reflections w = 1/[σ2(Fo2) + (0.007P)2 + 0.4P]
where P = (Fo2 + 2Fc2)/3
507 parameters(Δ/σ)max < 0.001
Crystal data top
C24H34O2S2β = 93.52 (15)°
Mr = 418.63γ = 95.39 (15)°
Triclinic, P1V = 564.4 (9) Å3
a = 5.047 (5) ÅZ = 1
b = 6.979 (6) ÅMo Kα radiation
c = 16.333 (9) ÅT = 100 K
α = 98.79 (16)°0.43 × 0.14 × 0.08 mm
Data collection top
Four-circle
diffractometer
9170 reflections with > 2.0σ(I)
70042 measured reflectionsRint = 0.053
9170 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043507 parameters
wR(F2) = 0.072342 restraints
S = 1.05Only H-atom coordinates refined
9169 reflections
Special details top

Refinement. Refinement of F2 against reflections. The threshold expression of F2 > σ(F2) is used for calculating R-factors(gt) 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
S10.60821 (4)0.17676 (3)0.195386 (12)0.01319 (4)
O10.2860 (3)0.10723 (16)0.10469 (8)0.0203 (2)
C11.3157 (3)1.27357 (19)0.43468 (8)0.0266 (3)
C21.2949 (2)1.05489 (14)0.42037 (6)0.01927 (17)
C31.11326 (19)0.98952 (13)0.35267 (5)0.01719 (15)
C41.08483 (18)0.77169 (12)0.34286 (5)0.01648 (15)
C50.91139 (17)0.70154 (12)0.27343 (5)0.01541 (14)
C60.87406 (17)0.48593 (11)0.26930 (5)0.01529 (14)
C70.69141 (16)0.41264 (11)0.20516 (5)0.01324 (13)
C80.56520 (19)0.51301 (12)0.14994 (6)0.01622 (15)
C90.39934 (18)0.39915 (12)0.09997 (5)0.01545 (15)
C100.40116 (15)0.21217 (10)0.11753 (4)0.01272 (12)
C110.25567 (16)0.05170 (12)0.08131 (5)0.01291 (13)
C120.07096 (16)0.08862 (11)0.01483 (5)0.01295 (12)
H1A1.4447 (18)1.3117 (17)0.4819 (5)0.04489
H1B1.1265 (11)1.3522 (14)0.4531 (8)0.04769
H1C1.391 (2)1.3194 (16)0.3796 (4)0.04903
H2A1.220 (3)1.0126 (14)0.4785 (2)0.03239
H2B1.4932 (6)0.9775 (11)0.4041 (9)0.03351
H3A0.9155 (7)1.0701 (11)0.3677 (9)0.03618
H3B1.194 (3)1.0238 (15)0.2936 (2)0.03684
H4A1.2833 (7)0.6916 (10)0.3301 (8)0.02987
H4B0.998 (2)0.7395 (14)0.4014 (2)0.02943
H5A0.7164 (8)0.7871 (9)0.2837 (9)0.03161
H5B1.004 (2)0.7246 (14)0.2140 (2)0.03174
H6A0.794 (3)0.4644 (14)0.33051 (19)0.02836
H6B1.0704 (7)0.4027 (9)0.2561 (9)0.02845
H80.586 (2)0.6645 (6)0.1461 (7)0.03114
H90.284 (2)0.4525 (12)0.0529 (6)0.02986
H12A0.074 (2)0.2126 (14)0.0402 (8)0.03017
H12B0.189 (2)0.131 (2)0.0366 (5)0.02884
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01592 (8)0.01142 (7)0.01319 (7)0.00276 (5)0.00391 (5)0.00308 (5)
O10.0247 (4)0.0130 (3)0.0262 (4)0.0048 (3)0.0126 (5)0.0071 (3)
C10.0371 (6)0.0204 (4)0.0229 (4)0.0134 (4)0.0041 (4)0.0013 (3)
C20.0208 (3)0.0188 (3)0.0183 (3)0.0073 (3)0.0034 (3)0.0009 (2)
C30.0199 (3)0.0163 (3)0.0163 (3)0.0071 (2)0.0030 (2)0.0015 (2)
C40.0189 (3)0.0153 (3)0.0157 (3)0.0057 (2)0.0035 (2)0.0009 (2)
C50.0176 (3)0.0138 (2)0.0153 (3)0.0051 (2)0.0031 (2)0.0013 (2)
C60.0180 (3)0.0135 (2)0.0150 (3)0.0041 (2)0.0048 (2)0.00158 (19)
C70.0157 (3)0.0115 (2)0.0130 (2)0.00263 (19)0.0038 (2)0.00168 (18)
C80.0199 (3)0.0118 (2)0.0186 (3)0.0040 (2)0.0070 (3)0.0041 (2)
C90.0182 (3)0.0124 (2)0.0174 (3)0.0031 (2)0.0065 (3)0.0043 (2)
C100.0139 (2)0.0112 (2)0.0136 (2)0.00213 (19)0.00347 (19)0.00217 (18)
C110.0138 (3)0.0113 (2)0.0141 (3)0.0020 (2)0.0034 (2)0.0023 (2)
C120.0139 (2)0.0120 (2)0.0134 (2)0.0025 (2)0.0027 (2)0.00221 (19)
H1A0.053560.039790.043800.017670.021400.00033
H1B0.042550.032380.065310.004610.006240.00246
H1C0.074000.040170.036960.024430.003750.00793
H2A0.036400.036180.024340.011800.002000.00087
H2B0.027520.037470.033090.007820.001230.00343
H3A0.033350.028410.044610.002270.007310.00224
H3B0.050010.036870.027440.019830.004280.00739
H4A0.023140.032340.031740.002910.000150.00171
H4B0.033260.033590.021590.010140.002700.00279
H5A0.027450.025810.039850.000060.005870.00018
H5B0.040590.034260.022770.014710.000750.00629
H6A0.033610.032230.020250.009760.001190.00482
H6B0.022140.028280.032660.000210.001920.00049
H80.042300.018210.036920.009630.012950.00919
H90.036160.025550.031640.004140.016420.01048
H12A0.026270.025950.035240.003740.005320.00204
H12B0.029760.033880.025110.008710.002900.00820
Geometric parameters (Å, º) top
S1—C71.7232 (13)C5—C61.5258 (11)
S1—C101.7264 (11)C5—H5A1.0914 (14)
O1—C111.2265 (10)C5—H5B1.0924 (10)
C1—C21.5227 (12)C6—C71.5007 (11)
C1—H1B1.0577 (14)C6—H6A1.0916 (10)
C1—H1A1.0587 (11)C6—H6B1.0926 (14)
C1—H1C1.0608 (10)C7—C81.3747 (9)
C2—C31.5231 (11)C8—C91.4174 (11)
C2—H2B1.0892 (14)C8—H81.0831 (11)
C2—H2A1.0920 (10)C9—C101.3776 (10)
C3—C41.5253 (12)C9—H91.0831 (11)
C3—H3B1.0918 (10)C10—C111.4659 (12)
C3—H3A1.0932 (14)C11—C121.5097 (10)
C4—C51.5246 (11)C12—H12A1.0916 (14)
C4—H4B1.0919 (10)C12—H12B1.0924 (11)
C4—H4A1.0921 (14)
C7—S1—C1092.24 (17)C5—C4—H4B109 (2)
C2—C1—H1B111 (3)C5—C4—H4A109 (2)
C2—C1—H1A111 (3)H4B—C4—H4A108 (4)
C2—C1—H1C111 (2)C6—C5—H5A109 (2)
H1B—C1—H1A108 (4)C6—C5—H5B109 (2)
H1B—C1—H1C108 (4)H5A—C5—H5B108 (4)
H1A—C1—H1C108 (4)C7—C6—C5113.8 (3)
C3—C2—C1113.7 (4)C7—C6—H6A109 (2)
C3—C2—H2B109 (2)C7—C6—H6B110 (2)
C3—C2—H2A109 (2)H6A—C6—H6B108 (5)
H2B—C2—H2A107 (5)C9—C8—H8124 (2)
C4—C3—H3B109 (2)C10—C9—C8112.7 (4)
C4—C3—H3A109 (2)C10—C9—H9123 (2)
H3B—C3—H3A108 (5)C11—C10—C9129.8 (5)
C5—C4—C3113.5 (3)H12A—C12—H12B107 (5)
S1—C7—C6—C5176.04 (4)C7—S1—C10—C90.36 (5)
S1—C7—C6—H6A55.3 (4)C7—C6—C5—H5A55.5 (4)
S1—C7—C6—H6B63.0 (4)C7—C6—C5—H5B62.4 (4)
S1—C7—C8—C90.40 (5)C7—C8—C9—C100.13 (6)
S1—C7—C8—H8178.9 (2)C7—C8—C9—H9180.0 (3)
S1—C10—C11—O11.79 (6)C8—C7—S1—C100.43 (5)
S1—C10—C11—C12178.52 (8)C8—C7—C6—H6A123.0 (8)
S1—C10—C9—C80.20 (5)C8—C7—C6—H6B118.8 (8)
S1—C10—C9—H9179.7 (2)C8—C9—C10—C11178.94 (6)
O1—C11—C10—C9179.13 (6)C9—C10—C11—C120.55 (5)
O1—C11—C12—H12A123.6 (8)C10—C11—C12—H12A56.7 (7)
O1—C11—C12—H12B120.4 (8)C10—C11—C12—H12B59.2 (7)
C1—C2—C3—C4176.99 (8)C10—C9—C8—H8178.6 (3)
C1—C2—C3—H3B61.8 (5)C11—C10—C9—H91.2 (4)
C1—C2—C3—H3A56.1 (5)H1A—C1—C2—H2B57.7 (8)
C2—C3—C4—C5178.04 (7)H1A—C1—C2—H2A58.9 (8)
C2—C3—C4—H4B60.8 (5)H1B—C1—C2—H2B177.6 (7)
C2—C3—C4—H4A56.8 (5)H1B—C1—C2—H2A61 (1)
C3—C2—C1—H1B60.5 (7)H1C—C1—C2—H2B62 (1)
C3—C2—C1—H1A179.63 (11)H1C—C1—C2—H2A179.0 (5)
C3—C2—C1—H1C59.5 (6)H2A—C2—C3—H3B176.7 (10)
C3—C4—C5—C6176.44 (6)H2A—C2—C3—H3A65 (1)
C3—C4—C5—H5A55.4 (4)H2B—C2—C3—H3B60 (1)
C3—C4—C5—H5B62.7 (5)H2B—C2—C3—H3A178 (1)
C4—C5—C6—C7176.59 (6)H3A—C3—C4—H4B60 (1)
C4—C5—C6—H6A55.0 (4)H3A—C3—C4—H4A178 (1)
C4—C5—C6—H6B61.6 (5)H3B—C3—C4—H4B178 (1)
C4—C3—C2—H2B60.8 (5)H3B—C3—C4—H4A65 (1)
C4—C3—C2—H2A55.5 (4)H4A—C4—C5—H5A177 (1)
C5—C4—C3—H3B56.7 (5)H4A—C4—C5—H5B59 (1)
C5—C4—C3—H3A60.8 (5)H4B—C4—C5—H5A66 (1)
C5—C6—C7—C82.17 (5)H4B—C4—C5—H5B176.3 (9)
C6—C7—S1—C10178.06 (5)H5A—C5—C6—H6A66 (1)
C6—C7—C8—C9177.95 (6)H5A—C5—C6—H6B177 (1)
C6—C7—C8—H80.5 (4)H5B—C5—C6—H6A176.0 (8)
C6—C5—C4—H4B55.4 (4)H5B—C5—C6—H6B59 (1)
C6—C5—C4—H4A62.4 (5)H8—C8—C9—H91.5 (5)
C7—S1—C10—C11178.88 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i1.08 (1)2.30 (1)3.095 (2)129 (1)
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC24H34O2S2
Mr418.63
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)5.047 (5), 6.979 (6), 16.333 (9)
α, β, γ (°)98.79 (16), 93.52 (15), 95.39 (15)
V3)564.4 (9)
Z1
Radiation typeMo Kα
µ (mm1)?
Crystal size (mm)0.43 × 0.14 × 0.08
Data collection
DiffractometerFour-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [ > 2.0σ(I)] reflections
70042, 9170, 9170
Rint0.053
(sin θ/λ)max1)1.026
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.072, 1.05
No. of reflections9169
No. of parameters507
No. of restraints342
H-atom treatmentOnly H-atom coordinates refined
Δρmax, Δρmin (e Å3)?, ?

Computer programs: MoPro (J. Appl. Cryst. 2005, 38, 38-54).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O1i1.0831 (11)2.301 (3)3.095 (2)128.6 (5)
Symmetry code: (i) x, y+1, z.
 

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