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It has been observed that when electron-rich naphthyl rings are present in chalcones they can participate in π–π stacking inter­actions, and this can play an important role in orientating inhibitors within the active sites of enzymes, while chalcones containing heterocyclic substituents additionally exhibit fungistatic and fungicidal properties. With these considerations in mind, three new chalcones containing 2-naphthyl substituents were prepared. 3-(4-Fluoro­phen­yl)-1-(naphthalen-2-yl)prop-2-en-1-one, C19H13FO, (I), crystallizes with Z′ = 2 in the space group P\overline{1} and the four mol­ecules in the unit cell adopt an arrangement which resembles that in the space group P21/a. Although 3-(4-bromo­phen­yl)-1-(naphthalen-2-yl)prop-2-en-1-one, C19H13BrO, (II), with Z′ = 1, is not iso­struc­tural with (I), the mol­ecules of (I) and (II) adopt very similar conformations. In 1-(naphthalen-2-yl)-3-(thio­phen-2-yl)prop-2-en-1-one, C17H12OS, (III), the thio­phene unit is disordered over two sets of atomic sites, with occupancies of 0.780 (3) and 0.220 (3), which are related by a near 180° rotation of the thio­phene unit about its exocyclic C—C bond. The mol­ecules of compound (I) are linked by three independent C—H...π(arene) hydrogen bonds to form centrosymmetric octa­molecular aggregates, whereas the mol­ecules of compound (II) are linked into mol­ecular ladders by a combination of C—H...π(arene) and C—Br...π(arene) inter­actions, and those of compound (III) are linked into centrosymmetric dimers by C—H...π(thio­phene) inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961700105X/sk3650sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650Isup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650IIsup6.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650IIIsup7.cml
Supplementary material

CCDC references: 1528834; 1528833; 1528832

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT-Plus (Bruker, 2012); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

(I) 3-(4-Fluorophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one top
Crystal data top
C19H13FOZ = 4
Mr = 276.29F(000) = 576
Triclinic, P1Dx = 1.336 Mg m3
a = 7.6678 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.5007 (5) ÅCell parameters from 6071 reflections
c = 15.7874 (8) Åθ = 1.3–27.2°
α = 96.249 (3)°µ = 0.09 mm1
β = 96.752 (3)°T = 296 K
γ = 90.796 (3)°Block, colourless
V = 1373.84 (12) Å30.41 × 0.32 × 0.30 mm
Data collection top
Bruker Kappa APEXII
diffractometer
3046 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.032
φ and ω scansθmax = 26.6°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 99
Tmin = 0.960, Tmax = 0.973k = 1414
25027 measured reflectionsl = 1919
5721 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.182 w = 1/[σ2(Fo2) + (0.0648P)2 + 0.5614P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
5721 reflectionsΔρmax = 0.21 e Å3
379 parametersΔρmin = 0.19 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.2636 (3)0.49245 (19)0.46846 (15)0.0455 (6)
O110.2606 (3)0.59900 (14)0.46856 (12)0.0680 (6)
C120.2197 (3)0.4364 (2)0.54308 (16)0.0538 (7)
H120.19130.35680.53620.065*
C130.2193 (3)0.49594 (19)0.61931 (16)0.0458 (6)
H130.25130.57490.62370.055*
C1110.2880 (3)0.45775 (18)0.31358 (15)0.0407 (5)
H1110.24160.53130.30880.049*
C1120.3106 (3)0.41720 (18)0.39246 (15)0.0421 (5)
C1130.3852 (3)0.30607 (19)0.39978 (16)0.0473 (6)
H1130.40060.27730.45290.057*
C1140.4342 (3)0.24143 (19)0.32976 (17)0.0488 (6)
H1140.48520.16950.33610.059*
C1150.4574 (3)0.2146 (2)0.17426 (18)0.0532 (6)
H1150.50560.14140.17880.064*
C1160.4343 (4)0.2558 (2)0.09649 (19)0.0648 (8)
H1160.46840.21130.04870.078*
C1170.3594 (4)0.3650 (2)0.08786 (18)0.0643 (7)
H1170.34340.39260.03430.077*
C1180.3100 (3)0.4308 (2)0.15763 (16)0.0530 (6)
H1180.26020.50310.15120.064*
C1190.3332 (3)0.39099 (18)0.23947 (15)0.0397 (5)
C1200.4100 (3)0.28039 (18)0.24811 (15)0.0425 (6)
C1310.1745 (3)0.45205 (18)0.69754 (15)0.0425 (6)
C1320.2077 (3)0.5214 (2)0.77522 (16)0.0508 (6)
H1320.26080.59490.77680.061*
C1330.1641 (4)0.4845 (2)0.85047 (17)0.0594 (7)
H1330.18830.53160.90240.071*
C1340.0843 (4)0.3767 (2)0.84632 (18)0.0589 (7)
F1340.0381 (3)0.34032 (16)0.91995 (11)0.0930 (6)
C1350.0490 (3)0.3046 (2)0.77151 (17)0.0536 (6)
H1350.00440.23130.77080.064*
C1360.0938 (3)0.3424 (2)0.69728 (17)0.0488 (6)
H1360.07010.29410.64590.059*
C210.2219 (3)1.00381 (19)0.54713 (15)0.0453 (6)
O210.2219 (3)1.10970 (14)0.54542 (11)0.0664 (5)
C220.2670 (3)0.9241 (2)0.47339 (15)0.0508 (6)
H220.29010.84640.48040.061*
C230.2750 (3)0.96147 (19)0.39753 (15)0.0455 (6)
H230.24761.03930.39320.055*
C2110.2104 (3)1.01657 (17)0.70294 (14)0.0398 (5)
H2110.25891.09180.70670.048*
C2120.1777 (3)0.95200 (18)0.62421 (15)0.0413 (5)
C2130.1001 (3)0.83855 (19)0.61895 (16)0.0470 (6)
H2130.07880.79370.56590.056*
C2140.0566 (3)0.79453 (19)0.69011 (16)0.0471 (6)
H2140.00220.72090.68490.057*
C2150.0533 (3)0.8133 (2)0.84710 (17)0.0533 (7)
H2150.00280.74040.84320.064*
C2160.0963 (4)0.8748 (2)0.92514 (18)0.0639 (7)
H2160.07230.84300.97440.077*
C2170.1770 (4)0.9862 (2)0.93198 (17)0.0619 (7)
H2170.20651.02800.98570.074*
C2180.2122 (3)1.0334 (2)0.86059 (16)0.0508 (6)
H2180.26361.10790.86590.061*
C2190.1722 (3)0.97130 (18)0.77841 (14)0.0391 (5)
C2200.0922 (3)0.85821 (18)0.77167 (15)0.0406 (5)
C2310.3216 (3)0.89484 (18)0.32013 (14)0.0407 (5)
C2320.2893 (3)0.9409 (2)0.24220 (16)0.0497 (6)
H2320.23921.01390.24070.060*
C2330.3301 (3)0.8805 (2)0.16714 (17)0.0578 (7)
H2330.30640.91130.11500.069*
C2340.4060 (4)0.7744 (2)0.17121 (17)0.0576 (7)
F2340.4474 (3)0.71518 (15)0.09738 (11)0.0926 (6)
C2350.4438 (3)0.7263 (2)0.24616 (16)0.0500 (6)
H2350.49760.65440.24690.060*
C2360.4009 (3)0.78637 (19)0.32071 (16)0.0466 (6)
H2360.42500.75420.37230.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0406 (14)0.0416 (13)0.0530 (15)0.0046 (10)0.0008 (11)0.0067 (11)
O110.0959 (15)0.0433 (10)0.0657 (12)0.0017 (9)0.0145 (10)0.0047 (8)
C120.0609 (17)0.0413 (13)0.0590 (17)0.0063 (11)0.0085 (13)0.0034 (12)
C130.0413 (14)0.0379 (12)0.0581 (16)0.0012 (10)0.0048 (11)0.0066 (11)
C1110.0335 (12)0.0328 (11)0.0558 (15)0.0008 (9)0.0003 (10)0.0104 (10)
C1120.0386 (13)0.0355 (11)0.0513 (15)0.0050 (10)0.0021 (11)0.0053 (10)
C1130.0405 (14)0.0455 (13)0.0557 (15)0.0025 (11)0.0029 (11)0.0145 (11)
C1140.0389 (14)0.0366 (12)0.0710 (18)0.0057 (10)0.0021 (12)0.0104 (12)
C1150.0421 (14)0.0449 (13)0.0724 (19)0.0025 (11)0.0119 (13)0.0004 (13)
C1160.0635 (19)0.0711 (18)0.0595 (19)0.0033 (15)0.0158 (14)0.0033 (15)
C1170.0679 (19)0.0714 (18)0.0541 (17)0.0033 (15)0.0041 (14)0.0133 (14)
C1180.0516 (16)0.0502 (14)0.0574 (17)0.0018 (12)0.0006 (13)0.0126 (12)
C1190.0297 (12)0.0379 (11)0.0510 (14)0.0041 (9)0.0013 (10)0.0069 (10)
C1200.0305 (12)0.0387 (12)0.0581 (16)0.0024 (9)0.0029 (11)0.0065 (11)
C1310.0348 (13)0.0371 (11)0.0553 (15)0.0043 (10)0.0028 (11)0.0056 (11)
C1320.0472 (15)0.0426 (13)0.0625 (17)0.0002 (11)0.0069 (12)0.0053 (12)
C1330.0583 (17)0.0612 (16)0.0557 (17)0.0013 (13)0.0004 (13)0.0008 (13)
C1340.0538 (17)0.0670 (17)0.0590 (18)0.0017 (13)0.0061 (13)0.0217 (14)
F1340.1102 (15)0.1042 (13)0.0695 (12)0.0169 (11)0.0150 (10)0.0292 (10)
C1350.0449 (15)0.0462 (13)0.0703 (19)0.0034 (11)0.0042 (13)0.0128 (13)
C1360.0424 (14)0.0442 (12)0.0592 (16)0.0009 (11)0.0046 (12)0.0053 (11)
C210.0457 (14)0.0402 (12)0.0480 (15)0.0016 (10)0.0018 (11)0.0038 (11)
O210.0979 (16)0.0444 (10)0.0589 (12)0.0038 (9)0.0149 (10)0.0084 (8)
C220.0614 (17)0.0417 (13)0.0499 (15)0.0062 (11)0.0045 (12)0.0096 (11)
C230.0435 (14)0.0382 (12)0.0553 (16)0.0015 (10)0.0063 (11)0.0066 (11)
C2110.0363 (12)0.0297 (10)0.0533 (15)0.0004 (9)0.0065 (10)0.0030 (10)
C2120.0388 (13)0.0346 (11)0.0501 (15)0.0049 (9)0.0030 (11)0.0054 (10)
C2130.0427 (14)0.0411 (12)0.0535 (15)0.0038 (10)0.0037 (11)0.0011 (11)
C2140.0413 (14)0.0353 (11)0.0640 (17)0.0023 (10)0.0022 (12)0.0070 (11)
C2150.0467 (15)0.0468 (13)0.0702 (19)0.0008 (11)0.0149 (13)0.0156 (13)
C2160.0690 (19)0.0683 (17)0.0595 (18)0.0029 (15)0.0199 (15)0.0162 (14)
C2170.0699 (19)0.0642 (17)0.0516 (17)0.0005 (14)0.0126 (14)0.0015 (13)
C2180.0526 (15)0.0428 (13)0.0567 (16)0.0008 (11)0.0100 (12)0.0004 (11)
C2190.0329 (12)0.0373 (11)0.0476 (14)0.0059 (9)0.0066 (10)0.0038 (10)
C2200.0296 (12)0.0363 (11)0.0559 (15)0.0025 (9)0.0031 (10)0.0069 (10)
C2310.0369 (13)0.0377 (11)0.0480 (14)0.0023 (10)0.0037 (10)0.0083 (10)
C2320.0457 (15)0.0450 (13)0.0607 (17)0.0005 (11)0.0063 (12)0.0167 (12)
C2330.0624 (18)0.0638 (16)0.0497 (16)0.0073 (14)0.0067 (13)0.0189 (13)
C2340.0617 (18)0.0574 (16)0.0555 (17)0.0070 (13)0.0192 (14)0.0020 (13)
F2340.1272 (16)0.0911 (12)0.0633 (11)0.0034 (11)0.0390 (11)0.0037 (9)
C2350.0463 (15)0.0433 (13)0.0622 (17)0.0019 (11)0.0129 (12)0.0065 (12)
C2360.0459 (14)0.0461 (13)0.0486 (15)0.0011 (11)0.0052 (11)0.0098 (11)
Geometric parameters (Å, º) top
C11—O111.226 (3)C21—O211.221 (2)
C11—C121.473 (3)C21—C221.478 (3)
C11—C1121.484 (3)C21—C2121.483 (3)
C12—C131.318 (3)C22—C231.323 (3)
C12—H120.9300C22—H220.9300
C13—C1311.459 (3)C23—C2311.454 (3)
C13—H130.9300C23—H230.9300
C111—C1121.370 (3)C211—C2121.371 (3)
C111—C1191.409 (3)C211—C2191.411 (3)
C111—H1110.9300C211—H2110.9300
C112—C1131.418 (3)C212—C2131.416 (3)
C113—C1141.357 (3)C213—C2141.355 (3)
C113—H1130.9300C213—H2130.9300
C114—C1201.403 (3)C214—C2201.406 (3)
C114—H1140.9300C214—H2140.9300
C115—C1161.357 (4)C215—C2161.354 (3)
C115—C1201.407 (3)C215—C2201.409 (3)
C115—H1150.9300C215—H2150.9300
C116—C1171.402 (4)C216—C2171.403 (4)
C116—H1160.9300C216—H2160.9300
C117—C1181.362 (3)C217—C2181.355 (3)
C117—H1170.9300C217—H2170.9300
C118—C1191.410 (3)C218—C2191.409 (3)
C118—H1180.9300C218—H2180.9300
C119—C1201.422 (3)C219—C2201.418 (3)
C131—C1321.383 (3)C231—C2321.389 (3)
C131—C1361.396 (3)C231—C2361.396 (3)
C132—C1331.379 (3)C232—C2331.378 (3)
C132—H1320.9300C232—H2320.9300
C133—C1341.368 (4)C233—C2341.364 (4)
C133—H1330.9300C233—H2330.9300
C134—F1341.360 (3)C234—F2341.358 (3)
C134—C1351.364 (4)C234—C2351.363 (3)
C135—C1361.372 (3)C235—C2361.375 (3)
C135—H1350.9300C235—H2350.9300
C136—H1360.9300C236—H2360.9300
O11—C11—C12120.9 (2)O21—C21—C22121.3 (2)
O11—C11—C112120.4 (2)O21—C21—C212120.4 (2)
C12—C11—C112118.7 (2)C22—C21—C212118.30 (19)
C13—C12—C11121.9 (2)C23—C22—C21121.2 (2)
C13—C12—H12119.1C23—C22—H22119.4
C11—C12—H12119.1C21—C22—H22119.4
C12—C13—C131127.4 (2)C22—C23—C231127.5 (2)
C12—C13—H13116.3C22—C23—H23116.3
C131—C13—H13116.3C231—C23—H23116.3
C112—C111—C119121.8 (2)C212—C211—C219121.39 (19)
C112—C111—H111119.1C212—C211—H211119.3
C119—C111—H111119.1C219—C211—H211119.3
C111—C112—C113118.9 (2)C211—C212—C213118.9 (2)
C111—C112—C11119.3 (2)C211—C212—C21119.02 (19)
C113—C112—C11121.7 (2)C213—C212—C21122.1 (2)
C114—C113—C112120.4 (2)C214—C213—C212120.9 (2)
C114—C113—H113119.8C214—C213—H213119.6
C112—C113—H113119.8C212—C213—H213119.6
C113—C114—C120121.7 (2)C213—C214—C220121.2 (2)
C113—C114—H114119.2C213—C214—H214119.4
C120—C114—H114119.2C220—C214—H214119.4
C116—C115—C120121.3 (2)C216—C215—C220121.0 (2)
C116—C115—H115119.4C216—C215—H215119.5
C120—C115—H115119.4C220—C215—H215119.5
C115—C116—C117120.3 (3)C215—C216—C217120.2 (2)
C115—C116—H116119.8C215—C216—H216119.9
C117—C116—H116119.8C217—C216—H216119.9
C118—C117—C116120.2 (3)C218—C217—C216120.3 (2)
C118—C117—H117119.9C218—C217—H217119.8
C116—C117—H117119.9C216—C217—H217119.8
C117—C118—C119120.9 (2)C217—C218—C219121.1 (2)
C117—C118—H118119.5C217—C218—H218119.4
C119—C118—H118119.5C219—C218—H218119.4
C111—C119—C118122.7 (2)C218—C219—C211122.6 (2)
C111—C119—C120118.6 (2)C218—C219—C220118.5 (2)
C118—C119—C120118.7 (2)C211—C219—C220118.9 (2)
C114—C120—C115122.9 (2)C214—C220—C215122.5 (2)
C114—C120—C119118.6 (2)C214—C220—C219118.8 (2)
C115—C120—C119118.5 (2)C215—C220—C219118.8 (2)
C132—C131—C136117.8 (2)C232—C231—C236118.0 (2)
C132—C131—C13119.8 (2)C232—C231—C23119.3 (2)
C136—C131—C13122.4 (2)C236—C231—C23122.7 (2)
C133—C132—C131121.8 (2)C233—C232—C231121.3 (2)
C133—C132—H132119.1C233—C232—H232119.4
C131—C132—H132119.1C231—C232—H232119.4
C134—C133—C132118.0 (2)C234—C233—C232118.3 (2)
C134—C133—H133121.0C234—C233—H233120.9
C132—C133—H133121.0C232—C233—H233120.9
F134—C134—C135118.9 (2)F234—C234—C235118.8 (2)
F134—C134—C133118.4 (3)F234—C234—C233118.3 (2)
C135—C134—C133122.7 (3)C235—C234—C233122.8 (2)
C134—C135—C136118.6 (2)C234—C235—C236118.6 (2)
C134—C135—H135120.7C234—C235—H235120.7
C136—C135—H135120.7C236—C235—H235120.7
C135—C136—C131121.2 (2)C235—C236—C231121.0 (2)
C135—C136—H136119.4C235—C236—H236119.5
C131—C136—H136119.4C231—C236—H236119.5
O11—C11—C12—C1317.5 (4)O21—C21—C22—C2313.5 (4)
C112—C11—C12—C13162.9 (2)C212—C21—C22—C23167.1 (2)
C11—C12—C13—C131178.4 (2)C21—C22—C23—C231178.3 (2)
C119—C111—C112—C1131.4 (3)C219—C211—C212—C2131.4 (3)
C119—C111—C112—C11178.89 (19)C219—C211—C212—C21179.5 (2)
O11—C11—C112—C11123.9 (3)O21—C21—C212—C21127.9 (3)
C12—C11—C112—C111155.7 (2)C22—C21—C212—C211151.6 (2)
O11—C11—C112—C113153.6 (2)O21—C21—C212—C213151.1 (2)
C12—C11—C112—C11326.8 (3)C22—C21—C212—C21329.4 (3)
C111—C112—C113—C1140.4 (3)C211—C212—C213—C2140.8 (3)
C11—C112—C113—C114177.0 (2)C21—C212—C213—C214178.2 (2)
C112—C113—C114—C1201.4 (3)C212—C213—C214—C2202.1 (3)
C120—C115—C116—C1171.0 (4)C220—C215—C216—C2171.6 (4)
C115—C116—C117—C1180.3 (4)C215—C216—C217—C2180.1 (4)
C116—C117—C118—C1190.1 (4)C216—C217—C218—C2191.2 (4)
C112—C111—C119—C118179.6 (2)C217—C218—C219—C211178.6 (2)
C112—C111—C119—C1202.2 (3)C217—C218—C219—C2200.6 (3)
C117—C118—C119—C111178.3 (2)C212—C211—C219—C218176.8 (2)
C117—C118—C119—C1200.2 (3)C212—C211—C219—C2202.3 (3)
C113—C114—C120—C115179.1 (2)C213—C214—C220—C215178.1 (2)
C113—C114—C120—C1190.5 (3)C213—C214—C220—C2191.2 (3)
C116—C115—C120—C114179.1 (2)C216—C215—C220—C214177.0 (2)
C116—C115—C120—C1191.3 (3)C216—C215—C220—C2192.2 (3)
C111—C119—C120—C1141.2 (3)C218—C219—C220—C214178.2 (2)
C118—C119—C120—C114179.5 (2)C211—C219—C220—C2141.0 (3)
C111—C119—C120—C115179.1 (2)C218—C219—C220—C2151.1 (3)
C118—C119—C120—C1150.8 (3)C211—C219—C220—C215179.7 (2)
C12—C13—C131—C132169.7 (2)C22—C23—C231—C232167.2 (2)
C12—C13—C131—C13612.1 (4)C22—C23—C231—C23613.9 (4)
C136—C131—C132—C1330.3 (4)C236—C231—C232—C2331.5 (3)
C13—C131—C132—C133178.6 (2)C23—C231—C232—C233179.5 (2)
C131—C132—C133—C1340.8 (4)C231—C232—C233—C2341.0 (4)
C132—C133—C134—F134178.9 (2)C232—C233—C234—F234179.5 (2)
C132—C133—C134—C1350.9 (4)C232—C233—C234—C2350.4 (4)
F134—C134—C135—C136179.2 (2)F234—C234—C235—C236179.7 (2)
C133—C134—C135—C1360.7 (4)C233—C234—C235—C2361.2 (4)
C134—C135—C136—C1310.2 (4)C234—C235—C236—C2310.6 (4)
C132—C131—C136—C1350.0 (3)C232—C231—C236—C2350.7 (3)
C13—C131—C136—C135178.3 (2)C23—C231—C236—C235179.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C132—H132···Cg1i0.932.883.557 (3)131
C135—H135···Cg2ii0.932.833.503 (3)130
C214—H214···Cg3ii0.932.873.554 (2)131
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
(II) 3-(4-Bromophenyl)-1-(naphthalen-2-yl)prop-2-en-1-one top
Crystal data top
C19H13BrOZ = 2
Mr = 337.19F(000) = 340
Triclinic, P1Dx = 1.563 Mg m3
a = 5.8714 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.8616 (7) ÅCell parameters from 3816 reflections
c = 15.5954 (13) Åθ = 1.3–29.8°
α = 95.007 (5)°µ = 2.86 mm1
β = 90.218 (5)°T = 296 K
γ = 92.179 (5)°Block, colourless
V = 716.58 (11) Å30.30 × 0.28 × 0.27 mm
Data collection top
Bruker Kappa APEXII
diffractometer
1842 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.054
φ and ω scansθmax = 26.6°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 77
Tmin = 0.451, Tmax = 0.462k = 99
12745 measured reflectionsl = 1919
2941 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0164P)2 + 0.6492P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2941 reflectionsΔρmax = 0.44 e Å3
190 parametersΔρmin = 0.47 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5068 (6)0.2375 (4)0.4774 (2)0.0415 (9)
O10.7111 (4)0.2606 (3)0.49106 (15)0.0566 (7)
C20.3387 (6)0.3049 (5)0.5402 (2)0.0460 (9)
H20.18970.31770.52200.055*
C30.3935 (6)0.3475 (4)0.6212 (2)0.0407 (9)
H30.54220.32680.63690.049*
C110.5650 (5)0.1296 (4)0.3265 (2)0.0341 (8)
H110.71030.18090.33140.041*
C120.4239 (5)0.1438 (4)0.3957 (2)0.0348 (8)
C130.2048 (6)0.0631 (5)0.3885 (2)0.0444 (9)
H130.10550.07340.43480.053*
C140.1380 (6)0.0292 (4)0.3146 (2)0.0454 (9)
H140.00520.08410.31180.055*
C150.2162 (6)0.1383 (4)0.1639 (3)0.0479 (10)
H150.07380.19440.15910.057*
C160.3583 (7)0.1484 (5)0.0960 (3)0.0541 (11)
H160.31270.21090.04510.065*
C170.5745 (7)0.0651 (5)0.1018 (2)0.0493 (10)
H170.67120.07270.05460.059*
C180.6430 (6)0.0265 (4)0.1759 (2)0.0403 (9)
H180.78670.08080.17920.048*
C190.4979 (5)0.0400 (4)0.2482 (2)0.0334 (8)
C200.2798 (6)0.0440 (4)0.2422 (2)0.0376 (8)
C310.2512 (5)0.4230 (4)0.6895 (2)0.0345 (8)
C320.3290 (5)0.4328 (4)0.7740 (2)0.0398 (9)
H320.46940.38850.78560.048*
C330.2048 (5)0.5061 (4)0.8411 (2)0.0402 (9)
H330.25960.51070.89730.048*
C340.0016 (5)0.5723 (4)0.8236 (2)0.0360 (8)
Br340.17324 (8)0.67362 (6)0.91526 (3)0.06341 (18)
C350.0841 (5)0.5658 (4)0.7406 (2)0.0387 (9)
H350.22380.61150.72950.046*
C360.0415 (5)0.4912 (4)0.6743 (2)0.0397 (9)
H360.01490.48630.61830.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.041 (2)0.049 (2)0.036 (2)0.0112 (19)0.0044 (17)0.0078 (18)
O10.0424 (16)0.083 (2)0.0434 (15)0.0066 (14)0.0013 (12)0.0014 (14)
C20.040 (2)0.057 (3)0.040 (2)0.0099 (18)0.0015 (17)0.0001 (19)
C30.036 (2)0.048 (2)0.039 (2)0.0035 (17)0.0025 (17)0.0061 (18)
C110.0291 (18)0.032 (2)0.041 (2)0.0014 (15)0.0002 (16)0.0047 (17)
C120.0329 (19)0.039 (2)0.033 (2)0.0062 (16)0.0026 (16)0.0052 (17)
C130.038 (2)0.050 (2)0.047 (2)0.0055 (18)0.0140 (18)0.013 (2)
C140.033 (2)0.039 (2)0.064 (3)0.0000 (17)0.0039 (19)0.008 (2)
C150.042 (2)0.035 (2)0.066 (3)0.0021 (17)0.017 (2)0.001 (2)
C160.069 (3)0.044 (2)0.049 (3)0.014 (2)0.012 (2)0.005 (2)
C170.058 (3)0.051 (2)0.040 (2)0.018 (2)0.0063 (19)0.003 (2)
C180.040 (2)0.041 (2)0.040 (2)0.0052 (17)0.0028 (17)0.0006 (18)
C190.036 (2)0.0306 (19)0.034 (2)0.0073 (16)0.0022 (16)0.0044 (16)
C200.035 (2)0.030 (2)0.049 (2)0.0027 (16)0.0056 (17)0.0034 (18)
C310.0363 (19)0.032 (2)0.035 (2)0.0004 (16)0.0020 (16)0.0039 (16)
C320.0321 (19)0.045 (2)0.043 (2)0.0045 (16)0.0002 (17)0.0077 (18)
C330.041 (2)0.044 (2)0.036 (2)0.0011 (17)0.0035 (17)0.0019 (17)
C340.0357 (19)0.031 (2)0.041 (2)0.0026 (16)0.0027 (16)0.0002 (17)
Br340.0648 (3)0.0676 (3)0.0562 (3)0.0145 (2)0.0149 (2)0.0101 (2)
C350.0284 (18)0.041 (2)0.048 (2)0.0027 (16)0.0000 (17)0.0092 (18)
C360.038 (2)0.046 (2)0.035 (2)0.0016 (17)0.0016 (16)0.0061 (18)
Geometric parameters (Å, º) top
C1—O11.221 (4)C16—C171.405 (5)
C1—C21.473 (5)C16—H160.9300
C1—C121.485 (5)C17—C181.359 (5)
C2—C31.314 (4)C17—H170.9300
C2—H20.9300C18—C191.414 (4)
C3—C311.456 (4)C18—H180.9300
C3—H30.9300C19—C201.417 (4)
C11—C121.363 (4)C31—C321.388 (4)
C11—C191.403 (4)C31—C361.389 (4)
C11—H110.9300C32—C331.375 (4)
C12—C131.413 (5)C32—H320.9300
C13—C141.355 (5)C33—C341.373 (4)
C13—H130.9300C33—H330.9300
C14—C201.405 (5)C34—C351.375 (4)
C14—H140.9300C34—Br341.889 (3)
C15—C161.349 (5)C35—C361.375 (4)
C15—C201.413 (5)C35—H350.9300
C15—H150.9300C36—H360.9300
O1—C1—C2121.0 (3)C16—C17—H17119.9
O1—C1—C12120.2 (3)C17—C18—C19120.6 (3)
C2—C1—C12118.9 (3)C17—C18—H18119.7
C3—C2—C1121.8 (3)C19—C18—H18119.7
C3—C2—H2119.1C11—C19—C18122.3 (3)
C1—C2—H2119.1C11—C19—C20118.7 (3)
C2—C3—C31128.3 (3)C18—C19—C20119.0 (3)
C2—C3—H3115.9C14—C20—C15123.4 (3)
C31—C3—H3115.9C14—C20—C19118.2 (3)
C12—C11—C19122.1 (3)C15—C20—C19118.4 (3)
C12—C11—H11118.9C32—C31—C36117.6 (3)
C19—C11—H11118.9C32—C31—C3119.3 (3)
C11—C12—C13118.7 (3)C36—C31—C3123.1 (3)
C11—C12—C1119.5 (3)C33—C32—C31122.0 (3)
C13—C12—C1121.8 (3)C33—C32—H32119.0
C14—C13—C12120.6 (3)C31—C32—H32119.0
C14—C13—H13119.7C34—C33—C32118.8 (3)
C12—C13—H13119.7C34—C33—H33120.6
C13—C14—C20121.7 (3)C32—C33—H33120.6
C13—C14—H14119.2C33—C34—C35121.0 (3)
C20—C14—H14119.2C33—C34—Br34119.1 (3)
C16—C15—C20121.2 (4)C35—C34—Br34119.9 (2)
C16—C15—H15119.4C36—C35—C34119.5 (3)
C20—C15—H15119.4C36—C35—H35120.2
C15—C16—C17120.5 (4)C34—C35—H35120.2
C15—C16—H16119.8C35—C36—C31121.1 (3)
C17—C16—H16119.8C35—C36—H36119.4
C18—C17—C16120.3 (3)C31—C36—H36119.4
C18—C17—H17119.9
O1—C1—C2—C319.8 (6)C13—C14—C20—C190.3 (5)
C12—C1—C2—C3161.6 (3)C16—C15—C20—C14179.8 (3)
C1—C2—C3—C31176.8 (3)C16—C15—C20—C190.2 (5)
C19—C11—C12—C131.1 (5)C11—C19—C20—C141.9 (4)
C19—C11—C12—C1178.8 (3)C18—C19—C20—C14180.0 (3)
O1—C1—C12—C1119.9 (5)C11—C19—C20—C15178.1 (3)
C2—C1—C12—C11158.6 (3)C18—C19—C20—C150.0 (5)
O1—C1—C12—C13157.7 (3)C2—C3—C31—C32169.5 (4)
C2—C1—C12—C1323.7 (5)C2—C3—C31—C3612.4 (6)
C11—C12—C13—C141.2 (5)C36—C31—C32—C330.3 (5)
C1—C12—C13—C14176.4 (3)C3—C31—C32—C33178.5 (3)
C12—C13—C14—C201.9 (5)C31—C32—C33—C340.4 (5)
C20—C15—C16—C170.1 (5)C32—C33—C34—C350.1 (5)
C15—C16—C17—C180.1 (5)C32—C33—C34—Br34179.9 (2)
C16—C17—C18—C190.3 (5)C33—C34—C35—C360.3 (5)
C12—C11—C19—C18179.3 (3)Br34—C34—C35—C36179.7 (2)
C12—C11—C19—C202.6 (5)C34—C35—C36—C310.4 (5)
C17—C18—C19—C11178.3 (3)C32—C31—C36—C350.0 (5)
C17—C18—C19—C200.2 (5)C3—C31—C36—C35178.0 (3)
C13—C14—C20—C15179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C32—H32···Cg4i0.932.853.513 (3)129
Symmetry code: (i) x+1, y, z+1.
(III) 1-(Naphthalen-2-yl)-3-(thiophen-2-yl)prop-2-en-1-one top
Crystal data top
C17H12OSZ = 2
Mr = 264.33F(000) = 276
Triclinic, P1Dx = 1.360 Mg m3
a = 5.8271 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.4489 (4) ÅCell parameters from 4247 reflections
c = 15.2068 (9) Åθ = 1.4–32.6°
α = 79.745 (3)°µ = 0.24 mm1
β = 84.427 (3)°T = 296 K
γ = 85.763 (3)°Block, colourless
V = 645.36 (6) Å30.25 × 0.20 × 0.15 mm
Data collection top
Bruker Kappa APEXII
diffractometer
2164 reflections with I > 2σ(I)
Radiation source: fine focus sealed tubeRint = 0.033
φ and ω scansθmax = 26.6°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 77
Tmin = 0.933, Tmax = 0.965k = 99
18170 measured reflectionsl = 1919
2694 independent reflections
Refinement top
Refinement on F215 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.0278P)2 + 0.8674P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
2694 reflectionsΔρmax = 0.23 e Å3
185 parametersΔρmin = 0.41 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.9718 (5)0.2608 (4)0.50120 (19)0.0423 (7)
O11.1716 (4)0.2701 (4)0.51604 (15)0.0639 (7)
C111.0710 (4)0.3045 (3)0.33771 (18)0.0349 (6)
H111.20550.35430.34810.042*
C120.9152 (4)0.2463 (3)0.40887 (18)0.0363 (6)
C130.7111 (5)0.1705 (4)0.3930 (2)0.0430 (7)
H130.60260.13400.44070.052*
C140.6715 (5)0.1503 (4)0.3085 (2)0.0450 (7)
H140.53830.09650.29970.054*
C150.7924 (5)0.1952 (4)0.1456 (2)0.0477 (7)
H150.66080.14230.13450.057*
C160.9447 (6)0.2570 (5)0.0761 (2)0.0549 (8)
H160.91770.24500.01820.066*
C171.1423 (6)0.3388 (4)0.0905 (2)0.0507 (8)
H171.24490.38290.04200.061*
C181.1860 (5)0.3546 (4)0.17489 (19)0.0395 (6)
H181.31920.40840.18360.047*
C191.0318 (4)0.2905 (3)0.24950 (18)0.0343 (6)
C200.8275 (4)0.2088 (3)0.23435 (19)0.0372 (6)
C20.7821 (5)0.2641 (4)0.57262 (19)0.0426 (7)0.780 (3)
H20.63160.29530.55770.051*0.780 (3)
C30.8251 (5)0.2231 (4)0.65741 (19)0.0406 (6)0.780 (3)
H30.97610.18310.66870.049*0.780 (3)
C320.6634 (4)0.2334 (3)0.73499 (18)0.0368 (6)0.780 (3)
S310.3958 (2)0.33969 (18)0.72951 (8)0.0440 (3)0.780 (3)
C330.7012 (11)0.1705 (10)0.8224 (4)0.0429 (13)0.780 (3)
H330.83700.10560.83950.051*0.780 (3)
C340.5200 (8)0.2109 (16)0.8849 (3)0.0480 (13)0.780 (3)
H340.52170.17840.94680.058*0.780 (3)
C350.3430 (8)0.3035 (10)0.8425 (3)0.0471 (12)0.780 (3)
H350.20670.34310.87210.057*0.780 (3)
C2A0.7821 (5)0.2641 (4)0.57262 (19)0.0426 (7)0.220 (3)
H2A0.63160.29530.55770.051*0.220 (3)
C3A0.8251 (5)0.2231 (4)0.65741 (19)0.0406 (6)0.220 (3)
H3A0.97610.18310.66870.049*0.220 (3)
C420.6634 (4)0.2334 (3)0.73499 (18)0.0368 (6)0.220 (3)
S410.7334 (11)0.1491 (11)0.8392 (3)0.0440 (3)0.220 (3)
C430.4393 (19)0.299 (3)0.7365 (8)0.0440 (3)0.220 (3)
H430.36810.34860.68470.053*0.220 (3)
C440.324 (2)0.287 (4)0.8227 (9)0.0471 (12)0.220 (3)
H440.17250.32850.83520.057*0.220 (3)
C450.467 (3)0.205 (6)0.8851 (8)0.0480 (13)0.220 (3)
H450.42300.18210.94630.058*0.220 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0371 (15)0.0436 (16)0.0433 (16)0.0010 (12)0.0020 (12)0.0009 (12)
O10.0390 (12)0.103 (2)0.0475 (13)0.0079 (12)0.0034 (10)0.0067 (13)
C110.0281 (12)0.0329 (13)0.0441 (15)0.0036 (10)0.0003 (11)0.0084 (11)
C120.0326 (13)0.0319 (13)0.0430 (15)0.0007 (10)0.0003 (11)0.0051 (11)
C130.0337 (14)0.0387 (15)0.0532 (18)0.0063 (11)0.0049 (12)0.0018 (13)
C140.0321 (14)0.0387 (15)0.067 (2)0.0068 (12)0.0059 (13)0.0144 (14)
C150.0404 (16)0.0443 (17)0.064 (2)0.0020 (13)0.0166 (14)0.0191 (15)
C160.058 (2)0.060 (2)0.0501 (19)0.0077 (16)0.0144 (15)0.0189 (16)
C170.0536 (18)0.0493 (18)0.0467 (18)0.0039 (14)0.0027 (14)0.0077 (14)
C180.0372 (14)0.0366 (14)0.0443 (16)0.0015 (11)0.0028 (12)0.0065 (12)
C190.0299 (12)0.0274 (12)0.0444 (15)0.0034 (10)0.0032 (11)0.0051 (11)
C200.0331 (13)0.0291 (13)0.0497 (16)0.0041 (10)0.0043 (11)0.0095 (11)
C20.0357 (14)0.0468 (16)0.0445 (16)0.0018 (12)0.0035 (12)0.0072 (13)
C30.0340 (14)0.0381 (15)0.0494 (17)0.0011 (11)0.0004 (12)0.0096 (12)
C320.0355 (14)0.0326 (13)0.0439 (15)0.0065 (11)0.0021 (11)0.0096 (11)
S310.0347 (6)0.0467 (8)0.0509 (6)0.0066 (4)0.0080 (4)0.0109 (4)
C330.044 (3)0.041 (3)0.043 (3)0.005 (2)0.020 (2)0.000 (2)
C340.057 (3)0.047 (2)0.0410 (17)0.015 (4)0.0007 (17)0.0066 (14)
C350.0433 (18)0.047 (2)0.056 (3)0.0085 (17)0.0066 (18)0.025 (2)
C2A0.0357 (14)0.0468 (16)0.0445 (16)0.0018 (12)0.0035 (12)0.0072 (13)
C3A0.0340 (14)0.0381 (15)0.0494 (17)0.0011 (11)0.0004 (12)0.0096 (12)
C420.0355 (14)0.0326 (13)0.0439 (15)0.0065 (11)0.0021 (11)0.0096 (11)
S410.0347 (6)0.0467 (8)0.0509 (6)0.0066 (4)0.0080 (4)0.0109 (4)
C430.0347 (6)0.0467 (8)0.0509 (6)0.0066 (4)0.0080 (4)0.0109 (4)
C440.0433 (18)0.047 (2)0.056 (3)0.0085 (17)0.0066 (18)0.025 (2)
C450.057 (3)0.047 (2)0.0410 (17)0.015 (4)0.0007 (17)0.0066 (14)
Geometric parameters (Å, º) top
C1—O11.217 (3)C19—C201.432 (4)
C1—C21.474 (4)C2—C31.315 (4)
C1—C121.497 (4)C2—H20.9300
C11—C121.372 (4)C3—C321.446 (4)
C11—C191.405 (4)C3—H30.9300
C11—H110.9300C32—C331.363 (6)
C12—C131.413 (4)C32—S311.698 (2)
C13—C141.364 (4)S31—C351.692 (5)
C13—H130.9300C33—C341.403 (7)
C14—C201.404 (4)C33—H330.9300
C14—H140.9300C34—C351.350 (5)
C15—C161.350 (5)C34—H340.9300
C15—C201.407 (4)C35—H350.9300
C15—H150.9300S41—C451.695 (7)
C16—C171.395 (5)C43—C441.404 (9)
C16—H160.9300C43—H430.9300
C17—C181.359 (4)C44—C451.352 (7)
C17—H170.9300C44—H440.9300
C18—C191.413 (4)C45—H450.9300
C18—H180.9300
O1—C1—C2121.2 (3)C14—C20—C15123.7 (3)
O1—C1—C12119.8 (3)C14—C20—C19118.3 (3)
C2—C1—C12118.9 (2)C15—C20—C19118.0 (3)
C12—C11—C19121.5 (2)C3—C2—C1120.2 (3)
C12—C11—H11119.3C3—C2—H2119.9
C19—C11—H11119.3C1—C2—H2119.9
C11—C12—C13119.2 (3)C2—C3—C32127.2 (2)
C11—C12—C1118.5 (2)C2—C3—H3116.4
C13—C12—C1122.3 (2)C32—C3—H3116.4
C14—C13—C12120.6 (3)C33—C32—C3126.9 (3)
C14—C13—H13119.7C33—C32—S31109.4 (3)
C12—C13—H13119.7C3—C32—S31123.67 (19)
C13—C14—C20121.4 (3)C35—S31—C3292.48 (19)
C13—C14—H14119.3C32—C33—C34115.0 (5)
C20—C14—H14119.3C32—C33—H33122.5
C16—C15—C20121.7 (3)C34—C33—H33122.5
C16—C15—H15119.1C35—C34—C33110.4 (5)
C20—C15—H15119.1C35—C34—H34124.8
C15—C16—C17120.4 (3)C33—C34—H34124.8
C15—C16—H16119.8C34—C35—S31112.7 (4)
C17—C16—H16119.8C34—C35—H35123.6
C18—C17—C16120.4 (3)S31—C35—H35123.6
C18—C17—H17119.8C44—C43—H43122.8
C16—C17—H17119.8C45—C44—C43110.2 (8)
C17—C18—C19120.9 (3)C45—C44—H44124.9
C17—C18—H18119.6C43—C44—H44124.9
C19—C18—H18119.6C44—C45—S41112.5 (7)
C11—C19—C18122.5 (2)C44—C45—H45123.8
C11—C19—C20118.9 (2)S41—C45—H45123.8
C18—C19—C20118.6 (3)
C19—C11—C12—C130.1 (4)C16—C15—C20—C190.2 (4)
C19—C11—C12—C1178.3 (2)C11—C19—C20—C141.6 (4)
O1—C1—C12—C1121.7 (4)C18—C19—C20—C14178.1 (2)
C2—C1—C12—C11158.1 (3)C11—C19—C20—C15179.6 (2)
O1—C1—C12—C13156.5 (3)C18—C19—C20—C150.6 (4)
C2—C1—C12—C1323.7 (4)O1—C1—C2—C320.2 (5)
C11—C12—C13—C141.8 (4)C12—C1—C2—C3160.0 (3)
C1—C12—C13—C14176.3 (3)C1—C2—C3—C32174.8 (3)
C12—C13—C14—C202.0 (4)C2—C3—C32—C33171.5 (5)
C20—C15—C16—C170.7 (5)C2—C3—C32—S3112.1 (4)
C15—C16—C17—C181.1 (5)C33—C32—S31—C351.4 (4)
C16—C17—C18—C190.6 (4)C3—C32—S31—C35175.6 (3)
C12—C11—C19—C18178.0 (2)C3—C32—C33—C34175.3 (6)
C12—C11—C19—C201.8 (4)S31—C32—C33—C341.5 (8)
C17—C18—C19—C11180.0 (3)C32—C33—C34—C350.9 (11)
C17—C18—C19—C200.2 (4)C33—C34—C35—S310.2 (10)
C13—C14—C20—C15178.4 (3)C32—S31—C35—C340.9 (6)
C13—C14—C20—C190.3 (4)C43—C44—C45—S411 (4)
C16—C15—C20—C14178.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C18—H18···Cg5i0.932.803.572 (4)141
Symmetry code: (i) x+2, y+1, z+1.
Selected torsion angles (°) for compounds (I)–(III) top
Parameter(I)(I)(II)(III)
x =12nilnil
Cx2—Cx1—Cx12—Cx11155.7 (2)151.6 (2)158.6 (3)158.1 (3)
Cx2—Cx3—Cx31—Cx32169.7 (2)167.2 (2)169.5 (4)
Cx2—Cx3—Cx32—Cx33171.1 (5)
Cx2—Cx3—Cx32—Sx41171.3 (4)
Hydrogen-bond parameters (Å, °) for compounds (I)–(III) top
CompoundD—H···AD—HH···AD···AD—H···A
(I)C132—H132···Cg1i0.932.883.557 (3)131
C135—H135···Cg2ii0.932.833.503 (3)130
C214—H214···Cg3ii0.932.873.554 (2)131
(II)C32—H32···Cg4iii0.932.853.513 (3)129
(III)C18—H18···Cg5iv0.932.803.572 (4)141
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y, -z+1; (iv) -x+2, -y+1, -z+1.

Cg1–Cg5 represent the centroids of the C115–C120, C231–C236, C111–C114/C120/C119, C15–C20 and S31/C32–C35 rings, respectively
Parameters (Å, °) for the C—Br···π(arene) interaction in compound (II) top
C—Br···CgC—BrBr···CgC···CgC—Br···Cg
C34—Br34···Cg4ii1.889 (3)3.7527 (15)4.620 (3)105.13 (10)
Symmetry code: (ii) -x, -y+1, -z+1.

Cg4 represents the centroid of the C15–C20 ring.
 

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