organic papers
o2350
Butcheret al. C17H17BrO2SC17H16OS doi:10.1107/S1600536806017508 Acta Cryst.(2006). E62, o2350–o2352 Acta Crystallographica Section EStructure Reports Online
ISSN 1600-5368
Chalcone and its hydroxobromo derivative:
a 1:1 mixed crystal containing chalcone and
2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]propan-1-one
Ray J. Butcher,a*
H. S. Yathirajan,bA. Mithun,c B. Narayanacand B. K. Sarojinid
aDepartment of Chemistry, Howard University,
525 College Street NW, Washington, DC 20059, USA,bDepartment of Studies in
Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,
c
Department of Chemistry, Mangalore University, Mangalagangotri 574 199, India, anddDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
Correspondence e-mail: raymond.butcher@nrl.navy.mil
Key indicators
Single-crystal X-ray study T= 446 K
Mean(C–C) = 0.003 A˚ Rfactor = 0.040 wRfactor = 0.115
Data-to-parameter ratio = 19.2
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 21 February 2006 Accepted 11 May 2006
#2006 International Union of Crystallography
All rights reserved
In the structure of a mixed crystal, C17H17BrO2SC17H16OS,
containing chalcone and 2-bromo-3-hydroxy-1-(4-methyl-phenyl)-3-[4-(methylsulfanyl)phenyl]propan-1-one, the two molecules are linked by a strong hydrogen bond between the alcohol H atom of 2-bromo-3-hydroxy-1-(4-methyl-phenyl)-3-[4-(methylsulfanyl)phenyl]propan-1-one and the ketone group of chalcone.
Comment
There is currently great demand for large and high quality ferroelectric or piezoelectric single crystals with minimum defects and inhomogenities. An important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application. Different types of crystals being used are semiconductor crystals, oxide crystals, alkali halide crystals and non-linear optical (NLO) crystals. The NLO effect in organic compounds originates from a strong donor–acceptor intermolecular interaction, a delocalized-electron system and the ability to crystallize in a non-centrosymmetric structure. Among several organic compounds reported for their NLO properties, chal-cone derivatives are prominent materials for their excellent blue light transmittance and good crystallizability. They provide the configuration necessary to show NLO activity, with two planar rings connected through a conjugated double bond (Goto et al., 1991; Uchidaet al., 1998; Tam et al., 1989; Indira et al., 2002). From a search of noncentrosymmetric chalcone derivatives in the Cambridge Structural Database (ConQuestVersion 1.8; Allen, 2002), it seems that a necessary but not sufficient condition (Tehet al., 2006) is substitution on either of the phenyl rings in the para position (Rabinovich, 1970; Araiet al., 1994; Rabinovich & Shakked, 1974; Ravish-ankaret al., 2005; Rabinovich & Schmidt, 1970; Liet al., 1992; Gupta et al., 2002; Turowska-Tyrket al., 2003; Zhenget al., 1992; Patil et al., 2006). It is speculated that, in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of a noncentrosymmetric crystal structure (Fichouet al., 1988). The molecular hyperpolarizability, , is strongly influenced not only by the electronic effect but also by the steric effect of the substituents (Choet al., 1996).
1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]prop-2-en-1-one in chloroform using commercial-grade bromine. However, single-crystal X-ray analysis revealed that compound (I) is a mixed crystal of
chalcone and 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]propan-1-one, as the bromination reaction is incomplete. The hydroxobromo derivative of chalcone is formed by the cleavage of a cyclic bromonium intermediate by nucleophilic attack of water on the bromo-nium ion instead of on the bromide ion (see scheme). Thus, some of the chalcone remains unreacted, giving a mixed crystal with 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl]propan-1-one linked by hydrogen bonding. Bromination was carried out in commercial-grade
bromine in chloroform, and moisture was not excluded. The reduction of the double bond in the chalcone derivative is confirmed by the structural results, which show the addition of an –OH function to C8A, and by the lengthening of the C8— C9 bond from 1.344 (3) for C8B—C9B to 1.505 (3) A˚ for C8A—C9Aand the change in the angles about C8Aand C9A from trigonal (sp2) to tetrahedral (sp3) values.
Experimental
To a solution of 1-(4-methylphenyl)-3-[4-(methylsulfanyl)-phenyl]prop-2-en-1-one (2.68 g, 0.01 mol) in chloroform (50 ml), bromine (1.60 g, 0.01 mol) in chloroform (20 ml) was added slowly with stirring. After the completion of the addition of the bromine solution, the reaction mixture was stirred for 24 h. Excess chloroform was distilled off under reduced pressure. The solid obtained was dried and recrystallized from acetone.
Crystal data
C17H17BrO2SC17H16OS
Mr= 633.63 Triclinic,P1
a= 10.5026 (15) A˚
b= 11.4926 (17) A˚
c= 13.1326 (19) A˚
= 97.173 (3)
= 98.157 (2)
= 104.125 (2)
V= 1500.5 (4) A˚3
Z= 2
Dx= 1.402 Mg m 3 MoKradiation
= 1.54 mm 1
T= 446 (2) K Chunk, colourless 0.500.400.35 mm
Data collection
Bruker APEXII CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin= 0.774,Tmax= 1.000
(expected range = 0.451–0.583)
26944 measured reflections 7025 independent reflections 5636 reflections withI> 2(I)
Rint= 0.070
max= 27.9
organic papers
[image:2.610.314.564.74.279.2] [image:2.610.114.226.121.371.2]Acta Cryst.(2006). E62, o2350–o2352 Butcheret al. C17H17BrO2SC17H16OS
o2351
Figure 1
[image:2.610.46.290.525.691.2]A view showing the two components of (I), linked by a strong hydrogen bond (dashed line) between the alcohol H atom of 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylthio)phenyl]propan-1-one and the ketone group of chalcone. Displacement ellipsoids are drawn at the 20% probability level.
Figure 2
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.040
wR(F2) = 0.115
S= 1.06 7025 reflections 366 parameters
H atoms treated by a mixture of independent and constrained refinement
w= 1/[2(F
o2) + (0.0705P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.001
max= 0.84 e A˚ 3
min= 0.62 e A˚ 3
Table 1
Selected geometric parameters (A˚ ,).
Br—C9A 1.978 (2)
S1A—C2A 1.762 (2)
S1A—C1A 1.802 (2)
S1B—C2B 1.762 (2)
S1B—C1B 1.796 (3)
O—C10B 1.236 (3)
O1A—C8A 1.478 (3)
O2A—C10A 1.225 (3)
C5A—C8A 1.511 (3)
C8A—C9A 1.505 (3)
C9A—C10A 1.520 (3)
C10A—C11A 1.490 (3)
C5B—C8B 1.459 (3)
C8B—C9B 1.344 (3)
C9B—C10B 1.477 (3)
C10B—C11B 1.492 (3)
O1A—C8A—C9A 106.17 (17) O1A—C8A—C5A 110.92 (18) C9A—C8A—C5A 113.62 (19) C8A—C9A—C10A 112.66 (19) C8A—C9A—Br 109.50 (15) C10A—C9A—Br 105.16 (15) O2A—C10A—C11A 121.2 (2) O2A—C10A—C9A 119.5 (2) C11A—C10A—C9A 119.30 (19)
C6B—C5B—C4B 118.2 (2) C6B—C5B—C8B 123.9 (2) C4B—C5B—C8B 118.0 (2) C9B—C8B—C5B 128.1 (2) C8B—C9B—C10B 119.8 (2) O—C10B—C9B 120.9 (2) O—C10B—C11B 119.5 (2) C9B—C10B—C11B 119.67 (19)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O1A—H1A O 0.82 1.95 2.760 (2) 170
All H atoms were initially located in a difference Fourier map. The methyl H atoms were then constrained to an ideal geometry, with C— H distances of 0.98 A˚ andUiso(H) = 1.5Ueq(C), but each group was
allowed to rotate freely about its C—C bond. The H attached to O1A was located in a difference Fourier map and idealized with O—H = 0.82 A˚ andUiso(H) = 1.5Ueq(O). All other H atoms were placed in
geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.95–1.00 A˚ and Uiso(H) = 1.2Ueq(C).
Data collection:SMART(Bruker, 1998); cell refinement: SAINT-Plus(Bruker, 1999); data reduction:SAINT-Plus; program(s) used to solve structure: SHELXS97(Sheldrick, 1990); program(s) used to refine structure:SHELXL97(Sheldrick, 1997a); molecular graphics: SHELXTL(Sheldrick, 1997b); software used to prepare material for publication:SHELXTL.
One of the authors (BKS) thanks AICTE, Government of India, New Delhi, for financial assistance under the Career Award for Young Teachers (CAYT) scheme.
References
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Goto, Y., Hayashi, A., Kimura, Y. & Nakayama, M. (1991).J. Cryst. Growth, 108, 688–698.
Gupta, S., Henk, S., Kees, G., Yeap, G.-Y., Susanti, I., Mahmood, W. A. K. W. & Gupta, P. S. (2002).Z. Kristallogr. New Cryst. Struct.217, 503.
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Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997a).SHELXL97. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997b). SHELXTL. Version 5.10. Bruker AXS Inc.,
Madison, Wisconsin, USA.
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organic papers
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sup-1 Acta Cryst. (2006). E62, o2350–o2352
supporting information
Acta Cryst. (2006). E62, o2350–o2352 [https://doi.org/10.1107/S1600536806017508]
Chalcone and its hydroxobromo derivative: a 1:1 mixed crystal containing
chalcone and
2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methyl-sulfanyl)phenyl]propan-1-one
Ray J. Butcher, H. S. Yathirajan, A. Mithun, B. Narayana and B. K. Sarojini
chalcone– 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylthio)phenyl]propan-1-one (1:1) co-crystal
Crystal data
C17H17BrO2S·C17H16OS
Mr = 633.63
Triclinic, P1
a = 10.5026 (15) Å
b = 11.4926 (17) Å
c = 13.1326 (19) Å
α = 97.173 (3)°
β = 98.157 (2)°
γ = 104.125 (2)°
V = 1500.5 (4) Å3
Z = 2
F(000) = 656
Dx = 1.402 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 5693 reflections
θ = 2.3–27.7°
µ = 1.54 mm−1
T = 446 K Chunk, colourless 0.50 × 0.40 × 0.35 mm
Data collection
Bruker APEXII CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)
Tmin = 0.774, Tmax = 1.000
26944 measured reflections 7025 independent reflections 5636 reflections with I > 2σ(I)
Rint = 0.070
θmax = 27.9°, θmin = 1.6°
h = −13→13
k = −15→15
l = −16→17
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.040
wR(F2) = 0.115
S = 1.06 7025 reflections 366 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0705P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.001
Δρmax = 0.84 e Å−3
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sup-2 Acta Cryst. (2006). E62, o2350–o2352
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 (Å2)
x y z Uiso*/Ueq
Br 0.03005 (2) 0.45464 (2) 0.151873 (19) 0.02873 (10)
S1A 0.53997 (6) 0.66369 (5) 0.59935 (5) 0.02248 (14)
S1B 0.67585 (6) 1.21666 (6) 0.87652 (5) 0.02310 (14)
O 0.05444 (16) 0.90981 (14) 0.32149 (13) 0.0231 (4)
O1A −0.05937 (15) 0.69175 (15) 0.38110 (12) 0.0207 (3)
H1A −0.0169 0.7562 0.3676 0.031*
O2A −0.24869 (16) 0.52948 (15) 0.18904 (13) 0.0253 (4)
C1A 0.5265 (3) 0.5459 (2) 0.67903 (19) 0.0266 (5)
H1AA 0.6104 0.5575 0.7242 0.040*
H1AB 0.5033 0.4679 0.6350 0.040*
H1AC 0.4586 0.5497 0.7202 0.040*
C2A 0.3801 (2) 0.62999 (19) 0.52182 (17) 0.0170 (4)
C3A 0.3611 (2) 0.71288 (19) 0.45518 (17) 0.0168 (4)
H3AA 0.4322 0.7782 0.4521 0.020*
C4A 0.2384 (2) 0.69892 (19) 0.39401 (17) 0.0172 (4)
H4AA 0.2274 0.7558 0.3513 0.021*
C5A 0.1297 (2) 0.59981 (19) 0.39542 (17) 0.0175 (4)
C6A 0.1517 (2) 0.5143 (2) 0.45789 (17) 0.0187 (4)
H6AA 0.0824 0.4459 0.4570 0.022*
C7A 0.2742 (2) 0.52842 (19) 0.52135 (17) 0.0175 (4)
H7AA 0.2856 0.4708 0.5632 0.021*
C8A −0.0079 (2) 0.5914 (2) 0.33701 (17) 0.0195 (5)
H8AA −0.0683 0.5139 0.3433 0.023*
C9A −0.0120 (2) 0.5991 (2) 0.22305 (18) 0.0207 (5)
H9AA 0.0529 0.6732 0.2151 0.025*
C10A −0.1500 (2) 0.59635 (19) 0.16709 (17) 0.0178 (4)
C11A −0.1624 (2) 0.67150 (19) 0.08346 (17) 0.0167 (4)
C12A −0.0530 (2) 0.7482 (2) 0.05471 (18) 0.0190 (5)
H12A 0.0329 0.7521 0.0872 0.023*
C13A −0.0713 (2) 0.8187 (2) −0.02186 (18) 0.0218 (5)
H13A 0.0026 0.8687 −0.0405 0.026*
C14A −0.1999 (2) 0.8154 (2) −0.07136 (19) 0.0238 (5)
C15A −0.3084 (2) 0.7368 (2) −0.04292 (19) 0.0261 (5)
H15A −0.3945 0.7317 −0.0758 0.031*
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H16A −0.3636 0.6153 0.0512 0.026*
C17A −0.2202 (3) 0.8951 (3) −0.1508 (2) 0.0373 (7)
H17A −0.2810 0.9407 −0.1317 0.056*
H17B −0.2564 0.8455 −0.2180 0.056*
H17C −0.1362 0.9501 −0.1535 0.056*
C1B 0.6675 (3) 1.3647 (2) 0.9328 (2) 0.0300 (6)
H1BA 0.7417 1.3994 0.9890 0.045*
H1BB 0.5856 1.3576 0.9591 0.045*
H1BC 0.6708 1.4163 0.8806 0.045*
C2B 0.5421 (2) 1.1698 (2) 0.77004 (17) 0.0172 (4)
C3B 0.5317 (2) 1.0591 (2) 0.70693 (18) 0.0189 (5)
H3BA 0.5939 1.0155 0.7224 0.023*
C4B 0.4303 (2) 1.01453 (19) 0.62234 (17) 0.0182 (4)
H4BA 0.4237 0.9401 0.5820 0.022*
C5B 0.3365 (2) 1.07912 (19) 0.59558 (17) 0.0155 (4)
C6B 0.3468 (2) 1.1896 (2) 0.65930 (17) 0.0175 (4)
H6BA 0.2850 1.2334 0.6435 0.021*
C7B 0.4479 (2) 1.2342 (2) 0.74564 (17) 0.0178 (4)
H7BA 0.4532 1.3074 0.7875 0.021*
C8B 0.2351 (2) 1.0281 (2) 0.50209 (17) 0.0173 (4)
H8BA 0.2317 0.9499 0.4709 0.021*
C9B 0.1461 (2) 1.0799 (2) 0.45540 (17) 0.0181 (4)
H9BA 0.1445 1.1581 0.4826 0.022*
C10B 0.0506 (2) 1.0122 (2) 0.36065 (17) 0.0175 (4)
C11B −0.0524 (2) 1.06744 (19) 0.31192 (17) 0.0156 (4)
C12B −0.1343 (2) 1.0060 (2) 0.21805 (17) 0.0189 (5)
H12B −0.1215 0.9338 0.1862 0.023*
C13B −0.2349 (2) 1.0517 (2) 0.17167 (18) 0.0201 (5)
H13B −0.2885 1.0100 0.1088 0.024*
C14B −0.2565 (2) 1.1586 (2) 0.21776 (18) 0.0190 (5)
C15B −0.1753 (2) 1.2197 (2) 0.31233 (18) 0.0199 (5)
H15B −0.1894 1.2910 0.3446 0.024*
C16B −0.0738 (2) 1.17545 (19) 0.35881 (18) 0.0183 (4)
H16B −0.0199 1.2177 0.4213 0.022*
C17B −0.3689 (2) 1.2070 (2) 0.17042 (19) 0.0251 (5)
H17D −0.4048 1.1639 0.1008 0.038*
H17E −0.3355 1.2921 0.1685 0.038*
H17F −0.4378 1.1958 0.2120 0.038*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
Br 0.03186 (15) 0.03133 (15) 0.02419 (15) 0.01448 (11) 0.00517 (10) −0.00329 (10)
S1A 0.0162 (3) 0.0264 (3) 0.0253 (3) 0.0078 (2) 0.0013 (2) 0.0047 (2)
S1B 0.0187 (3) 0.0277 (3) 0.0198 (3) 0.0069 (2) −0.0034 (2) −0.0009 (2)
O 0.0279 (9) 0.0175 (8) 0.0225 (9) 0.0101 (7) −0.0028 (7) −0.0014 (7)
O1A 0.0174 (8) 0.0290 (9) 0.0189 (8) 0.0114 (7) 0.0058 (6) 0.0026 (7)
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sup-4 Acta Cryst. (2006). E62, o2350–o2352
C1A 0.0294 (13) 0.0322 (13) 0.0221 (13) 0.0156 (11) 0.0025 (10) 0.0070 (11)
C2A 0.0176 (10) 0.0170 (10) 0.0172 (11) 0.0076 (9) 0.0048 (9) −0.0023 (9)
C3A 0.0159 (10) 0.0137 (10) 0.0213 (11) 0.0033 (8) 0.0064 (9) 0.0023 (9)
C4A 0.0216 (11) 0.0148 (10) 0.0151 (11) 0.0051 (9) 0.0021 (9) 0.0028 (8)
C5A 0.0183 (10) 0.0175 (10) 0.0164 (11) 0.0045 (9) 0.0034 (9) 0.0013 (9)
C6A 0.0199 (11) 0.0149 (10) 0.0201 (12) 0.0023 (9) 0.0040 (9) 0.0021 (9)
C7A 0.0221 (11) 0.0146 (10) 0.0181 (11) 0.0083 (9) 0.0048 (9) 0.0025 (9)
C8A 0.0213 (11) 0.0163 (10) 0.0195 (11) 0.0040 (9) 0.0011 (9) 0.0029 (9)
C9A 0.0197 (11) 0.0191 (11) 0.0235 (12) 0.0041 (9) 0.0042 (9) 0.0058 (9)
C10A 0.0175 (10) 0.0173 (10) 0.0184 (11) 0.0065 (9) 0.0025 (9) −0.0008 (9)
C11A 0.0184 (11) 0.0154 (10) 0.0165 (11) 0.0071 (8) 0.0026 (8) −0.0016 (8)
C12A 0.0143 (10) 0.0213 (11) 0.0209 (11) 0.0058 (9) 0.0019 (9) 0.0013 (9)
C13A 0.0194 (11) 0.0222 (11) 0.0241 (12) 0.0066 (9) 0.0038 (9) 0.0034 (10)
C14A 0.0232 (12) 0.0277 (12) 0.0217 (12) 0.0109 (10) 0.0014 (9) 0.0031 (10)
C15A 0.0170 (11) 0.0363 (14) 0.0255 (13) 0.0109 (10) −0.0019 (9) 0.0060 (11)
C16A 0.0137 (10) 0.0261 (12) 0.0245 (12) 0.0055 (9) 0.0032 (9) 0.0024 (10)
C17A 0.0288 (14) 0.0478 (17) 0.0390 (16) 0.0125 (13) 0.0020 (12) 0.0213 (14)
C1B 0.0241 (12) 0.0318 (14) 0.0267 (13) 0.0049 (11) −0.0045 (10) −0.0073 (11)
C2B 0.0140 (10) 0.0220 (11) 0.0141 (10) 0.0024 (8) 0.0018 (8) 0.0032 (9)
C3B 0.0177 (11) 0.0184 (11) 0.0226 (12) 0.0073 (9) 0.0019 (9) 0.0073 (9)
C4B 0.0195 (11) 0.0130 (10) 0.0204 (11) 0.0028 (8) 0.0022 (9) 0.0014 (9)
C5B 0.0148 (10) 0.0159 (10) 0.0152 (11) 0.0023 (8) 0.0030 (8) 0.0039 (8)
C6B 0.0157 (10) 0.0196 (11) 0.0182 (11) 0.0068 (8) 0.0030 (8) 0.0026 (9)
C7B 0.0161 (10) 0.0166 (10) 0.0190 (11) 0.0033 (8) 0.0024 (9) −0.0012 (9)
C8B 0.0167 (10) 0.0149 (10) 0.0180 (11) 0.0007 (8) 0.0036 (8) 0.0003 (9)
C9B 0.0185 (11) 0.0155 (10) 0.0183 (11) 0.0039 (8) 0.0002 (9) −0.0004 (9)
C10B 0.0180 (10) 0.0167 (10) 0.0174 (11) 0.0043 (8) 0.0026 (9) 0.0025 (9)
C11B 0.0163 (10) 0.0137 (10) 0.0169 (11) 0.0044 (8) 0.0029 (8) 0.0024 (8)
C12B 0.0212 (11) 0.0164 (10) 0.0190 (11) 0.0077 (9) 0.0028 (9) −0.0011 (9)
C13B 0.0186 (11) 0.0244 (12) 0.0153 (11) 0.0046 (9) 0.0000 (9) 0.0014 (9)
C14B 0.0171 (10) 0.0189 (11) 0.0248 (12) 0.0065 (9) 0.0070 (9) 0.0105 (9)
C15B 0.0228 (11) 0.0144 (10) 0.0238 (12) 0.0073 (9) 0.0056 (9) 0.0012 (9)
C16B 0.0191 (11) 0.0137 (10) 0.0195 (11) 0.0024 (8) 0.0006 (9) −0.0005 (9)
C17B 0.0243 (12) 0.0274 (12) 0.0258 (13) 0.0122 (10) 0.0019 (10) 0.0056 (10)
Geometric parameters (Å, º)
Br—C9A 1.978 (2) C16A—H16A 0.9300
S1A—C2A 1.762 (2) C17A—H17A 0.9600
S1A—C1A 1.802 (2) C17A—H17B 0.9600
S1B—C2B 1.762 (2) C17A—H17C 0.9600
S1B—C1B 1.796 (3) C1B—H1BA 0.9600
O—C10B 1.236 (3) C1B—H1BB 0.9600
O1A—C8A 1.478 (3) C1B—H1BC 0.9600
O1A—H1A 0.8200 C2B—C7B 1.398 (3)
O2A—C10A 1.225 (3) C2B—C3B 1.400 (3)
C1A—H1AA 0.9600 C3B—C4B 1.374 (3)
supporting information
sup-5 Acta Cryst. (2006). E62, o2350–o2352
C1A—H1AC 0.9600 C4B—C5B 1.403 (3)
C2A—C7A 1.401 (3) C4B—H4BA 0.9300
C2A—C3A 1.402 (3) C5B—C6B 1.402 (3)
C3A—C4A 1.381 (3) C5B—C8B 1.459 (3)
C3A—H3AA 0.9300 C6B—C7B 1.387 (3)
C4A—C5A 1.406 (3) C6B—H6BA 0.9300
C4A—H4AA 0.9300 C7B—H7BA 0.9300
C5A—C6A 1.397 (3) C8B—C9B 1.344 (3)
C5A—C8A 1.511 (3) C8B—H8BA 0.9300
C6A—C7A 1.391 (3) C9B—C10B 1.477 (3)
C6A—H6AA 0.9300 C9B—H9BA 0.9300
C7A—H7AA 0.9300 C10B—C11B 1.492 (3)
C8A—C9A 1.505 (3) C11B—C12B 1.394 (3)
C8A—H8AA 0.9800 C11B—C16B 1.398 (3)
C9A—C10A 1.520 (3) C12B—C13B 1.390 (3)
C9A—H9AA 0.9800 C12B—H12B 0.9300
C10A—C11A 1.490 (3) C13B—C14B 1.384 (3)
C11A—C16A 1.390 (3) C13B—H13B 0.9300
C11A—C12A 1.397 (3) C14B—C15B 1.397 (3)
C12A—C13A 1.389 (3) C14B—C17B 1.513 (3)
C12A—H12A 0.9300 C15B—C16B 1.387 (3)
C13A—C14A 1.402 (3) C15B—H15B 0.9300
C13A—H13A 0.9300 C16B—H16B 0.9300
C14A—C15A 1.399 (3) C17B—H17D 0.9600
C14A—C17A 1.498 (3) C17B—H17E 0.9600
C15A—C16A 1.384 (3) C17B—H17F 0.9600
C15A—H15A 0.9300
C2A—S1A—C1A 103.93 (11) H17A—C17A—H17B 109.5
C2B—S1B—C1B 104.26 (12) C14A—C17A—H17C 109.5
C8A—O1A—H1A 109.5 H17A—C17A—H17C 109.5
S1A—C1A—H1AA 109.5 H17B—C17A—H17C 109.5
S1A—C1A—H1AB 109.5 S1B—C1B—H1BA 109.5
H1AA—C1A—H1AB 109.5 S1B—C1B—H1BB 109.5
S1A—C1A—H1AC 109.5 H1BA—C1B—H1BB 109.5
H1AA—C1A—H1AC 109.5 S1B—C1B—H1BC 109.5
H1AB—C1A—H1AC 109.5 H1BA—C1B—H1BC 109.5
C7A—C2A—C3A 118.9 (2) H1BB—C1B—H1BC 109.5
C7A—C2A—S1A 125.46 (17) C7B—C2B—C3B 119.1 (2)
C3A—C2A—S1A 115.67 (16) C7B—C2B—S1B 124.89 (17)
C4A—C3A—C2A 120.9 (2) C3B—C2B—S1B 116.02 (17)
C4A—C3A—H3AA 119.5 C4B—C3B—C2B 120.4 (2)
C2A—C3A—H3AA 119.5 C4B—C3B—H3BA 119.8
C3A—C4A—C5A 120.9 (2) C2B—C3B—H3BA 119.8
C3A—C4A—H4AA 119.6 C3B—C4B—C5B 121.3 (2)
C5A—C4A—H4AA 119.6 C3B—C4B—H4BA 119.4
C6A—C5A—C4A 117.7 (2) C5B—C4B—H4BA 119.4
supporting information
sup-6 Acta Cryst. (2006). E62, o2350–o2352
C4A—C5A—C8A 120.76 (19) C6B—C5B—C8B 123.9 (2)
C7A—C6A—C5A 122.0 (2) C4B—C5B—C8B 118.0 (2)
C7A—C6A—H6AA 119.0 C7B—C6B—C5B 120.8 (2)
C5A—C6A—H6AA 119.0 C7B—C6B—H6BA 119.6
C6A—C7A—C2A 119.5 (2) C5B—C6B—H6BA 119.6
C6A—C7A—H7AA 120.2 C6B—C7B—C2B 120.3 (2)
C2A—C7A—H7AA 120.2 C6B—C7B—H7BA 119.8
O1A—C8A—C9A 106.17 (17) C2B—C7B—H7BA 119.8
O1A—C8A—C5A 110.92 (18) C9B—C8B—C5B 128.1 (2)
C9A—C8A—C5A 113.62 (19) C9B—C8B—H8BA 115.9
O1A—C8A—H8AA 108.7 C5B—C8B—H8BA 115.9
C9A—C8A—H8AA 108.7 C8B—C9B—C10B 119.8 (2)
C5A—C8A—H8AA 108.7 C8B—C9B—H9BA 120.1
C8A—C9A—C10A 112.66 (19) C10B—C9B—H9BA 120.1
C8A—C9A—Br 109.50 (15) O—C10B—C9B 120.9 (2)
C10A—C9A—Br 105.16 (15) O—C10B—C11B 119.5 (2)
C8A—C9A—H9AA 109.8 C9B—C10B—C11B 119.67 (19)
C10A—C9A—H9AA 109.8 C12B—C11B—C16B 118.8 (2)
Br—C9A—H9AA 109.8 C12B—C11B—C10B 118.50 (19)
O2A—C10A—C11A 121.2 (2) C16B—C11B—C10B 122.6 (2)
O2A—C10A—C9A 119.5 (2) C13B—C12B—C11B 120.6 (2)
C11A—C10A—C9A 119.30 (19) C13B—C12B—H12B 119.7
C16A—C11A—C12A 118.6 (2) C11B—C12B—H12B 119.7
C16A—C11A—C10A 117.9 (2) C14B—C13B—C12B 120.8 (2)
C12A—C11A—C10A 123.4 (2) C14B—C13B—H13B 119.6
C13A—C12A—C11A 120.7 (2) C12B—C13B—H13B 119.6
C13A—C12A—H12A 119.7 C13B—C14B—C15B 118.7 (2)
C11A—C12A—H12A 119.7 C13B—C14B—C17B 121.5 (2)
C12A—C13A—C14A 120.8 (2) C15B—C14B—C17B 119.8 (2)
C12A—C13A—H13A 119.6 C16B—C15B—C14B 121.0 (2)
C14A—C13A—H13A 119.6 C16B—C15B—H15B 119.5
C15A—C14A—C13A 117.9 (2) C14B—C15B—H15B 119.5
C15A—C14A—C17A 121.1 (2) C15B—C16B—C11B 120.2 (2)
C13A—C14A—C17A 121.0 (2) C15B—C16B—H16B 119.9
C16A—C15A—C14A 121.2 (2) C11B—C16B—H16B 119.9
C16A—C15A—H15A 119.4 C14B—C17B—H17D 109.5
C14A—C15A—H15A 119.4 C14B—C17B—H17E 109.5
C15A—C16A—C11A 120.8 (2) H17D—C17B—H17E 109.5
C15A—C16A—H16A 119.6 C14B—C17B—H17F 109.5
C11A—C16A—H16A 119.6 H17D—C17B—H17F 109.5
C14A—C17A—H17A 109.5 H17E—C17B—H17F 109.5
C14A—C17A—H17B 109.5
C1A—S1A—C2A—C7A −3.8 (2) C14A—C15A—C16A—C11A −0.4 (4)
C1A—S1A—C2A—C3A 176.85 (16) C12A—C11A—C16A—C15A −0.6 (3)
C7A—C2A—C3A—C4A 3.5 (3) C10A—C11A—C16A—C15A 178.1 (2)
S1A—C2A—C3A—C4A −177.18 (17) C1B—S1B—C2B—C7B −4.9 (2)
supporting information
sup-7 Acta Cryst. (2006). E62, o2350–o2352
C3A—C4A—C5A—C6A −2.2 (3) C7B—C2B—C3B—C4B −0.1 (3)
C3A—C4A—C5A—C8A 173.7 (2) S1B—C2B—C3B—C4B 179.65 (17)
C4A—C5A—C6A—C7A 3.4 (3) C2B—C3B—C4B—C5B 1.3 (3)
C8A—C5A—C6A—C7A −172.5 (2) C3B—C4B—C5B—C6B −1.7 (3)
C5A—C6A—C7A—C2A −1.2 (3) C3B—C4B—C5B—C8B 177.5 (2)
C3A—C2A—C7A—C6A −2.3 (3) C4B—C5B—C6B—C7B 0.8 (3)
S1A—C2A—C7A—C6A 178.45 (17) C8B—C5B—C6B—C7B −178.3 (2)
C6A—C5A—C8A—O1A 111.3 (2) C5B—C6B—C7B—C2B 0.4 (3)
C4A—C5A—C8A—O1A −64.5 (3) C3B—C2B—C7B—C6B −0.7 (3)
C6A—C5A—C8A—C9A −129.2 (2) S1B—C2B—C7B—C6B 179.50 (17)
C4A—C5A—C8A—C9A 55.0 (3) C6B—C5B—C8B—C9B 7.4 (4)
O1A—C8A—C9A—C10A −55.2 (2) C4B—C5B—C8B—C9B −171.7 (2)
C5A—C8A—C9A—C10A −177.36 (18) C5B—C8B—C9B—C10B −179.8 (2)
O1A—C8A—C9A—Br −171.83 (13) C8B—C9B—C10B—O −2.5 (3)
C5A—C8A—C9A—Br 66.0 (2) C8B—C9B—C10B—C11B 177.0 (2)
C8A—C9A—C10A—O2A −38.8 (3) O—C10B—C11B—C12B −5.5 (3)
Br—C9A—C10A—O2A 80.4 (2) C9B—C10B—C11B—C12B 175.0 (2)
C8A—C9A—C10A—C11A 143.7 (2) O—C10B—C11B—C16B 171.7 (2)
Br—C9A—C10A—C11A −97.14 (19) C9B—C10B—C11B—C16B −7.8 (3)
O2A—C10A—C11A—C16A 2.1 (3) C16B—C11B—C12B—C13B 0.3 (3)
C9A—C10A—C11A—C16A 179.6 (2) C10B—C11B—C12B—C13B 177.7 (2)
O2A—C10A—C11A—C12A −179.3 (2) C11B—C12B—C13B—C14B −0.3 (3)
C9A—C10A—C11A—C12A −1.8 (3) C12B—C13B—C14B—C15B −0.2 (3)
C16A—C11A—C12A—C13A 0.5 (3) C12B—C13B—C14B—C17B −177.6 (2)
C10A—C11A—C12A—C13A −178.1 (2) C13B—C14B—C15B—C16B 0.8 (3)
C11A—C12A—C13A—C14A 0.6 (4) C17B—C14B—C15B—C16B 178.3 (2)
C12A—C13A—C14A—C15A −1.5 (4) C14B—C15B—C16B—C11B −0.8 (3)
C12A—C13A—C14A—C17A 177.4 (2) C12B—C11B—C16B—C15B 0.2 (3)
C13A—C14A—C15A—C16A 1.4 (4) C10B—C11B—C16B—C15B −177.0 (2)
C17A—C14A—C15A—C16A −177.5 (2)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
![Figure 1A view showing the two components of (I), linked by a strong hydrogenbond (dashed line) between the alcohol H atom of 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylthio)phenyl]propan-1-one and the ketonegroup of chalcone](https://thumb-us.123doks.com/thumbv2/123dok_us/666636.569057/2.610.114.226.121.371/figure-components-hydrogenbond-hydroxy-methylphenyl-methylthio-ketonegroup-chalcone.webp)
