Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supra­moleular assembly mediated by C—H⋯π and C—Br⋯π inter­actions

Girisha, M.; Sagar, B.K.; Yathirajan, H.S.; Rathore, R.S.; Glidewell, C.

doi:10.1107/S205322961700105X

Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—Hπ and C—Brπ interactions

M. Girisha, B. K. Sagar, H. S. Yathirajan, R. S. Rathore and C. Glidewell

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.

Keywords: chalcones; crystal structure; pseudosymmetry; disorder; molecular conformation; molecular aggregate; hydrogen bonding; C—Br

π bonding; Claisen–Schmidt condensation reaction.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961700105X/sk3650sup1.cif Contains datablocks global, I, II, III
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S205322961700105X/sk3650IIIsup4.hkl Contains datablock III
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650Isup5.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S205322961700105X/sk3650IIsup6.cml Supplementary material
	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

C₁₉H₁₃FO	Z = 4
M_r = 276.29	F(000) = 576
Triclinic, P1	D_x = 1.336 Mg m⁻³
a = 7.6678 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.5007 (5) Å	Cell parameters from 6071 reflections
c = 15.7874 (8) Å	θ = 1.3–27.2°
α = 96.249 (3)°	µ = 0.09 mm⁻¹
β = 96.752 (3)°	T = 296 K
γ = 90.796 (3)°	Block, colourless
V = 1373.84 (12) Å³	0.41 × 0.32 × 0.30 mm

Data collection top

Bruker Kappa APEXII diffractometer	3046 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.032
φ and ω scans	θ_max = 26.6°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −9→9
T_min = 0.960, T_max = 0.973	k = −14→14
25027 measured reflections	l = −19→19
5721 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.182	w = 1/[σ²(F_o²) + (0.0648P)² + 0.5614P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
5721 reflections	Δρ_max = 0.21 e Å⁻³
379 parameters	Δρ_min = −0.19 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C11	0.2636 (3)	0.49245 (19)	0.46846 (15)	0.0455 (6)
O11	0.2606 (3)	0.59900 (14)	0.46856 (12)	0.0680 (6)
C12	0.2197 (3)	0.4364 (2)	0.54308 (16)	0.0538 (7)
H12	0.1913	0.3568	0.5362	0.065*
C13	0.2193 (3)	0.49594 (19)	0.61931 (16)	0.0458 (6)
H13	0.2513	0.5749	0.6237	0.055*
C111	0.2880 (3)	0.45775 (18)	0.31358 (15)	0.0407 (5)
H111	0.2416	0.5313	0.3088	0.049*
C112	0.3106 (3)	0.41720 (18)	0.39246 (15)	0.0421 (5)
C113	0.3852 (3)	0.30607 (19)	0.39978 (16)	0.0473 (6)
H113	0.4006	0.2773	0.4529	0.057*
C114	0.4342 (3)	0.24143 (19)	0.32976 (17)	0.0488 (6)
H114	0.4852	0.1695	0.3361	0.059*
C115	0.4574 (3)	0.2146 (2)	0.17426 (18)	0.0532 (6)
H115	0.5056	0.1414	0.1788	0.064*
C116	0.4343 (4)	0.2558 (2)	0.09649 (19)	0.0648 (8)
H116	0.4684	0.2113	0.0487	0.078*
C117	0.3594 (4)	0.3650 (2)	0.08786 (18)	0.0643 (7)
H117	0.3434	0.3926	0.0343	0.077*
C118	0.3100 (3)	0.4308 (2)	0.15763 (16)	0.0530 (6)
H118	0.2602	0.5031	0.1512	0.064*
C119	0.3332 (3)	0.39099 (18)	0.23947 (15)	0.0397 (5)
C120	0.4100 (3)	0.28039 (18)	0.24811 (15)	0.0425 (6)
C131	0.1745 (3)	0.45205 (18)	0.69754 (15)	0.0425 (6)
C132	0.2077 (3)	0.5214 (2)	0.77522 (16)	0.0508 (6)
H132	0.2608	0.5949	0.7768	0.061*
C133	0.1641 (4)	0.4845 (2)	0.85047 (17)	0.0594 (7)
H133	0.1883	0.5316	0.9024	0.071*
C134	0.0843 (4)	0.3767 (2)	0.84632 (18)	0.0589 (7)
F134	0.0381 (3)	0.34032 (16)	0.91995 (11)	0.0930 (6)
C135	0.0490 (3)	0.3046 (2)	0.77151 (17)	0.0536 (6)
H135	−0.0044	0.2313	0.7708	0.064*
C136	0.0938 (3)	0.3424 (2)	0.69728 (17)	0.0488 (6)
H136	0.0701	0.2941	0.6459	0.059*
C21	0.2219 (3)	1.00381 (19)	0.54713 (15)	0.0453 (6)
O21	0.2219 (3)	1.10970 (14)	0.54542 (11)	0.0664 (5)
C22	0.2670 (3)	0.9241 (2)	0.47339 (15)	0.0508 (6)
H22	0.2901	0.8464	0.4804	0.061*
C23	0.2750 (3)	0.96147 (19)	0.39753 (15)	0.0455 (6)
H23	0.2476	1.0393	0.3932	0.055*
C211	0.2104 (3)	1.01657 (17)	0.70294 (14)	0.0398 (5)
H211	0.2589	1.0918	0.7067	0.048*
C212	0.1777 (3)	0.95200 (18)	0.62421 (15)	0.0413 (5)
C213	0.1001 (3)	0.83855 (19)	0.61895 (16)	0.0470 (6)
H213	0.0788	0.7937	0.5659	0.056*
C214	0.0566 (3)	0.79453 (19)	0.69011 (16)	0.0471 (6)
H214	0.0022	0.7209	0.6849	0.057*
C215	0.0533 (3)	0.8133 (2)	0.84710 (17)	0.0533 (7)
H215	−0.0028	0.7404	0.8432	0.064*
C216	0.0963 (4)	0.8748 (2)	0.92514 (18)	0.0639 (7)
H216	0.0723	0.8430	0.9744	0.077*
C217	0.1770 (4)	0.9862 (2)	0.93198 (17)	0.0619 (7)
H217	0.2065	1.0280	0.9857	0.074*
C218	0.2122 (3)	1.0334 (2)	0.86059 (16)	0.0508 (6)
H218	0.2636	1.1079	0.8659	0.061*
C219	0.1722 (3)	0.97130 (18)	0.77841 (14)	0.0391 (5)
C220	0.0922 (3)	0.85821 (18)	0.77167 (15)	0.0406 (5)
C231	0.3216 (3)	0.89484 (18)	0.32013 (14)	0.0407 (5)
C232	0.2893 (3)	0.9409 (2)	0.24220 (16)	0.0497 (6)
H232	0.2392	1.0139	0.2407	0.060*
C233	0.3301 (3)	0.8805 (2)	0.16714 (17)	0.0578 (7)
H233	0.3064	0.9113	0.1150	0.069*
C234	0.4060 (4)	0.7744 (2)	0.17121 (17)	0.0576 (7)
F234	0.4474 (3)	0.71518 (15)	0.09738 (11)	0.0926 (6)
C235	0.4438 (3)	0.7263 (2)	0.24616 (16)	0.0500 (6)
H235	0.4976	0.6544	0.2469	0.060*
C236	0.4009 (3)	0.78637 (19)	0.32071 (16)	0.0466 (6)
H236	0.4250	0.7542	0.3723	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0406 (14)	0.0416 (13)	0.0530 (15)	−0.0046 (10)	−0.0008 (11)	0.0067 (11)
O11	0.0959 (15)	0.0433 (10)	0.0657 (12)	−0.0017 (9)	0.0145 (10)	0.0047 (8)
C12	0.0609 (17)	0.0413 (13)	0.0590 (17)	−0.0063 (11)	0.0085 (13)	0.0034 (12)
C13	0.0413 (14)	0.0379 (12)	0.0581 (16)	0.0012 (10)	0.0048 (11)	0.0066 (11)
C111	0.0335 (12)	0.0328 (11)	0.0558 (15)	0.0008 (9)	0.0003 (10)	0.0104 (10)
C112	0.0386 (13)	0.0355 (11)	0.0513 (15)	−0.0050 (10)	0.0021 (11)	0.0053 (10)
C113	0.0405 (14)	0.0455 (13)	0.0557 (15)	−0.0025 (11)	−0.0029 (11)	0.0145 (11)
C114	0.0389 (14)	0.0366 (12)	0.0710 (18)	0.0057 (10)	0.0021 (12)	0.0104 (12)
C115	0.0421 (14)	0.0449 (13)	0.0724 (19)	0.0025 (11)	0.0119 (13)	0.0004 (13)
C116	0.0635 (19)	0.0711 (18)	0.0595 (19)	−0.0033 (15)	0.0158 (14)	−0.0033 (15)
C117	0.0679 (19)	0.0714 (18)	0.0541 (17)	−0.0033 (15)	0.0041 (14)	0.0133 (14)
C118	0.0516 (16)	0.0502 (14)	0.0574 (17)	0.0018 (12)	0.0006 (13)	0.0126 (12)
C119	0.0297 (12)	0.0379 (11)	0.0510 (14)	−0.0041 (9)	0.0013 (10)	0.0069 (10)
C120	0.0305 (12)	0.0387 (12)	0.0581 (16)	−0.0024 (9)	0.0029 (11)	0.0065 (11)
C131	0.0348 (13)	0.0371 (11)	0.0553 (15)	0.0043 (10)	0.0028 (11)	0.0056 (11)
C132	0.0472 (15)	0.0426 (13)	0.0625 (17)	0.0002 (11)	0.0069 (12)	0.0053 (12)
C133	0.0583 (17)	0.0612 (16)	0.0557 (17)	−0.0013 (13)	0.0004 (13)	0.0008 (13)
C134	0.0538 (17)	0.0670 (17)	0.0590 (18)	0.0017 (13)	0.0061 (13)	0.0217 (14)
F134	0.1102 (15)	0.1042 (13)	0.0695 (12)	−0.0169 (11)	0.0150 (10)	0.0292 (10)
C135	0.0449 (15)	0.0462 (13)	0.0703 (19)	−0.0034 (11)	0.0042 (13)	0.0128 (13)
C136	0.0424 (14)	0.0442 (12)	0.0592 (16)	0.0009 (11)	0.0046 (12)	0.0053 (11)
C21	0.0457 (14)	0.0402 (12)	0.0480 (15)	0.0016 (10)	−0.0018 (11)	0.0038 (11)
O21	0.0979 (16)	0.0444 (10)	0.0589 (12)	0.0038 (9)	0.0149 (10)	0.0084 (8)
C22	0.0614 (17)	0.0417 (13)	0.0499 (15)	0.0062 (11)	0.0045 (12)	0.0096 (11)
C23	0.0435 (14)	0.0382 (12)	0.0553 (16)	0.0015 (10)	0.0063 (11)	0.0066 (11)
C211	0.0363 (12)	0.0297 (10)	0.0533 (15)	0.0004 (9)	0.0065 (10)	0.0030 (10)
C212	0.0388 (13)	0.0346 (11)	0.0501 (15)	0.0049 (9)	0.0030 (11)	0.0054 (10)
C213	0.0427 (14)	0.0411 (12)	0.0535 (15)	0.0038 (10)	−0.0037 (11)	−0.0011 (11)
C214	0.0413 (14)	0.0353 (11)	0.0640 (17)	−0.0023 (10)	0.0022 (12)	0.0070 (11)
C215	0.0467 (15)	0.0468 (13)	0.0702 (19)	−0.0008 (11)	0.0149 (13)	0.0156 (13)
C216	0.0690 (19)	0.0683 (17)	0.0595 (18)	0.0029 (15)	0.0199 (15)	0.0162 (14)
C217	0.0699 (19)	0.0642 (17)	0.0516 (17)	0.0005 (14)	0.0126 (14)	0.0015 (13)
C218	0.0526 (15)	0.0428 (13)	0.0567 (16)	0.0008 (11)	0.0100 (12)	0.0004 (11)
C219	0.0329 (12)	0.0373 (11)	0.0476 (14)	0.0059 (9)	0.0066 (10)	0.0038 (10)
C220	0.0296 (12)	0.0363 (11)	0.0559 (15)	0.0025 (9)	0.0031 (10)	0.0069 (10)
C231	0.0369 (13)	0.0377 (11)	0.0480 (14)	−0.0023 (10)	0.0037 (10)	0.0083 (10)
C232	0.0457 (15)	0.0450 (13)	0.0607 (17)	0.0005 (11)	0.0063 (12)	0.0167 (12)
C233	0.0624 (18)	0.0638 (16)	0.0497 (16)	−0.0073 (14)	0.0067 (13)	0.0189 (13)
C234	0.0617 (18)	0.0574 (16)	0.0555 (17)	−0.0070 (13)	0.0192 (14)	0.0020 (13)
F234	0.1272 (16)	0.0911 (12)	0.0633 (11)	0.0034 (11)	0.0390 (11)	−0.0037 (9)
C235	0.0463 (15)	0.0433 (13)	0.0622 (17)	0.0019 (11)	0.0129 (12)	0.0065 (12)
C236	0.0459 (14)	0.0461 (13)	0.0486 (15)	−0.0011 (11)	0.0052 (11)	0.0098 (11)

Geometric parameters (Å, º) top

C11—O11	1.226 (3)	C21—O21	1.221 (2)
C11—C12	1.473 (3)	C21—C22	1.478 (3)
C11—C112	1.484 (3)	C21—C212	1.483 (3)
C12—C13	1.318 (3)	C22—C23	1.323 (3)
C12—H12	0.9300	C22—H22	0.9300
C13—C131	1.459 (3)	C23—C231	1.454 (3)
C13—H13	0.9300	C23—H23	0.9300
C111—C112	1.370 (3)	C211—C212	1.371 (3)
C111—C119	1.409 (3)	C211—C219	1.411 (3)
C111—H111	0.9300	C211—H211	0.9300
C112—C113	1.418 (3)	C212—C213	1.416 (3)
C113—C114	1.357 (3)	C213—C214	1.355 (3)
C113—H113	0.9300	C213—H213	0.9300
C114—C120	1.403 (3)	C214—C220	1.406 (3)
C114—H114	0.9300	C214—H214	0.9300
C115—C116	1.357 (4)	C215—C216	1.354 (3)
C115—C120	1.407 (3)	C215—C220	1.409 (3)
C115—H115	0.9300	C215—H215	0.9300
C116—C117	1.402 (4)	C216—C217	1.403 (4)
C116—H116	0.9300	C216—H216	0.9300
C117—C118	1.362 (3)	C217—C218	1.355 (3)
C117—H117	0.9300	C217—H217	0.9300
C118—C119	1.410 (3)	C218—C219	1.409 (3)
C118—H118	0.9300	C218—H218	0.9300
C119—C120	1.422 (3)	C219—C220	1.418 (3)
C131—C132	1.383 (3)	C231—C232	1.389 (3)
C131—C136	1.396 (3)	C231—C236	1.396 (3)
C132—C133	1.379 (3)	C232—C233	1.378 (3)
C132—H132	0.9300	C232—H232	0.9300
C133—C134	1.368 (4)	C233—C234	1.364 (4)
C133—H133	0.9300	C233—H233	0.9300
C134—F134	1.360 (3)	C234—F234	1.358 (3)
C134—C135	1.364 (4)	C234—C235	1.363 (3)
C135—C136	1.372 (3)	C235—C236	1.375 (3)
C135—H135	0.9300	C235—H235	0.9300
C136—H136	0.9300	C236—H236	0.9300

O11—C11—C12	120.9 (2)	O21—C21—C22	121.3 (2)
O11—C11—C112	120.4 (2)	O21—C21—C212	120.4 (2)
C12—C11—C112	118.7 (2)	C22—C21—C212	118.30 (19)
C13—C12—C11	121.9 (2)	C23—C22—C21	121.2 (2)
C13—C12—H12	119.1	C23—C22—H22	119.4
C11—C12—H12	119.1	C21—C22—H22	119.4
C12—C13—C131	127.4 (2)	C22—C23—C231	127.5 (2)
C12—C13—H13	116.3	C22—C23—H23	116.3
C131—C13—H13	116.3	C231—C23—H23	116.3
C112—C111—C119	121.8 (2)	C212—C211—C219	121.39 (19)
C112—C111—H111	119.1	C212—C211—H211	119.3
C119—C111—H111	119.1	C219—C211—H211	119.3
C111—C112—C113	118.9 (2)	C211—C212—C213	118.9 (2)
C111—C112—C11	119.3 (2)	C211—C212—C21	119.02 (19)
C113—C112—C11	121.7 (2)	C213—C212—C21	122.1 (2)
C114—C113—C112	120.4 (2)	C214—C213—C212	120.9 (2)
C114—C113—H113	119.8	C214—C213—H213	119.6
C112—C113—H113	119.8	C212—C213—H213	119.6
C113—C114—C120	121.7 (2)	C213—C214—C220	121.2 (2)
C113—C114—H114	119.2	C213—C214—H214	119.4
C120—C114—H114	119.2	C220—C214—H214	119.4
C116—C115—C120	121.3 (2)	C216—C215—C220	121.0 (2)
C116—C115—H115	119.4	C216—C215—H215	119.5
C120—C115—H115	119.4	C220—C215—H215	119.5
C115—C116—C117	120.3 (3)	C215—C216—C217	120.2 (2)
C115—C116—H116	119.8	C215—C216—H216	119.9
C117—C116—H116	119.8	C217—C216—H216	119.9
C118—C117—C116	120.2 (3)	C218—C217—C216	120.3 (2)
C118—C117—H117	119.9	C218—C217—H217	119.8
C116—C117—H117	119.9	C216—C217—H217	119.8
C117—C118—C119	120.9 (2)	C217—C218—C219	121.1 (2)
C117—C118—H118	119.5	C217—C218—H218	119.4
C119—C118—H118	119.5	C219—C218—H218	119.4
C111—C119—C118	122.7 (2)	C218—C219—C211	122.6 (2)
C111—C119—C120	118.6 (2)	C218—C219—C220	118.5 (2)
C118—C119—C120	118.7 (2)	C211—C219—C220	118.9 (2)
C114—C120—C115	122.9 (2)	C214—C220—C215	122.5 (2)
C114—C120—C119	118.6 (2)	C214—C220—C219	118.8 (2)
C115—C120—C119	118.5 (2)	C215—C220—C219	118.8 (2)
C132—C131—C136	117.8 (2)	C232—C231—C236	118.0 (2)
C132—C131—C13	119.8 (2)	C232—C231—C23	119.3 (2)
C136—C131—C13	122.4 (2)	C236—C231—C23	122.7 (2)
C133—C132—C131	121.8 (2)	C233—C232—C231	121.3 (2)
C133—C132—H132	119.1	C233—C232—H232	119.4
C131—C132—H132	119.1	C231—C232—H232	119.4
C134—C133—C132	118.0 (2)	C234—C233—C232	118.3 (2)
C134—C133—H133	121.0	C234—C233—H233	120.9
C132—C133—H133	121.0	C232—C233—H233	120.9
F134—C134—C135	118.9 (2)	F234—C234—C235	118.8 (2)
F134—C134—C133	118.4 (3)	F234—C234—C233	118.3 (2)
C135—C134—C133	122.7 (3)	C235—C234—C233	122.8 (2)
C134—C135—C136	118.6 (2)	C234—C235—C236	118.6 (2)
C134—C135—H135	120.7	C234—C235—H235	120.7
C136—C135—H135	120.7	C236—C235—H235	120.7
C135—C136—C131	121.2 (2)	C235—C236—C231	121.0 (2)
C135—C136—H136	119.4	C235—C236—H236	119.5
C131—C136—H136	119.4	C231—C236—H236	119.5

O11—C11—C12—C13	−17.5 (4)	O21—C21—C22—C23	−13.5 (4)
C112—C11—C12—C13	162.9 (2)	C212—C21—C22—C23	167.1 (2)
C11—C12—C13—C131	178.4 (2)	C21—C22—C23—C231	178.3 (2)
C119—C111—C112—C113	1.4 (3)	C219—C211—C212—C213	1.4 (3)
C119—C111—C112—C11	178.89 (19)	C219—C211—C212—C21	−179.5 (2)
O11—C11—C112—C111	−23.9 (3)	O21—C21—C212—C211	−27.9 (3)
C12—C11—C112—C111	155.7 (2)	C22—C21—C212—C211	151.6 (2)
O11—C11—C112—C113	153.6 (2)	O21—C21—C212—C213	151.1 (2)
C12—C11—C112—C113	−26.8 (3)	C22—C21—C212—C213	−29.4 (3)
C111—C112—C113—C114	0.4 (3)	C211—C212—C213—C214	0.8 (3)
C11—C112—C113—C114	−177.0 (2)	C21—C212—C213—C214	−178.2 (2)
C112—C113—C114—C120	−1.4 (3)	C212—C213—C214—C220	−2.1 (3)
C120—C115—C116—C117	−1.0 (4)	C220—C215—C216—C217	1.6 (4)
C115—C116—C117—C118	0.3 (4)	C215—C216—C217—C218	0.1 (4)
C116—C117—C118—C119	0.1 (4)	C216—C217—C218—C219	−1.2 (4)
C112—C111—C119—C118	179.6 (2)	C217—C218—C219—C211	−178.6 (2)
C112—C111—C119—C120	−2.2 (3)	C217—C218—C219—C220	0.6 (3)
C117—C118—C119—C111	178.3 (2)	C212—C211—C219—C218	176.8 (2)
C117—C118—C119—C120	0.2 (3)	C212—C211—C219—C220	−2.3 (3)
C113—C114—C120—C115	−179.1 (2)	C213—C214—C220—C215	−178.1 (2)
C113—C114—C120—C119	0.5 (3)	C213—C214—C220—C219	1.2 (3)
C116—C115—C120—C114	−179.1 (2)	C216—C215—C220—C214	177.0 (2)
C116—C115—C120—C119	1.3 (3)	C216—C215—C220—C219	−2.2 (3)
C111—C119—C120—C114	1.2 (3)	C218—C219—C220—C214	−178.2 (2)
C118—C119—C120—C114	179.5 (2)	C211—C219—C220—C214	1.0 (3)
C111—C119—C120—C115	−179.1 (2)	C218—C219—C220—C215	1.1 (3)
C118—C119—C120—C115	−0.8 (3)	C211—C219—C220—C215	−179.7 (2)
C12—C13—C131—C132	169.7 (2)	C22—C23—C231—C232	167.2 (2)
C12—C13—C131—C136	−12.1 (4)	C22—C23—C231—C236	−13.9 (4)
C136—C131—C132—C133	0.3 (4)	C236—C231—C232—C233	1.5 (3)
C13—C131—C132—C133	178.6 (2)	C23—C231—C232—C233	−179.5 (2)
C131—C132—C133—C134	−0.8 (4)	C231—C232—C233—C234	−1.0 (4)
C132—C133—C134—F134	−178.9 (2)	C232—C233—C234—F234	−179.5 (2)
C132—C133—C134—C135	0.9 (4)	C232—C233—C234—C235	−0.4 (4)
F134—C134—C135—C136	179.2 (2)	F234—C234—C235—C236	−179.7 (2)
C133—C134—C135—C136	−0.7 (4)	C233—C234—C235—C236	1.2 (4)
C134—C135—C136—C131	0.2 (4)	C234—C235—C236—C231	−0.6 (4)
C132—C131—C136—C135	0.0 (3)	C232—C231—C236—C235	−0.7 (3)
C13—C131—C136—C135	−178.3 (2)	C23—C231—C236—C235	−179.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C132—H132···Cg1ⁱ	0.93	2.88	3.557 (3)	131
C135—H135···Cg2ⁱⁱ	0.93	2.83	3.503 (3)	130
C214—H214···Cg3ⁱⁱ	0.93	2.87	3.554 (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

C₁₉H₁₃BrO	Z = 2
M_r = 337.19	F(000) = 340
Triclinic, P1	D_x = 1.563 Mg m⁻³
a = 5.8714 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.8616 (7) Å	Cell parameters from 3816 reflections
c = 15.5954 (13) Å	θ = 1.3–29.8°
α = 95.007 (5)°	µ = 2.86 mm⁻¹
β = 90.218 (5)°	T = 296 K
γ = 92.179 (5)°	Block, colourless
V = 716.58 (11) Å³	0.30 × 0.28 × 0.27 mm

Data collection top

Bruker Kappa APEXII diffractometer	1842 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.054
φ and ω scans	θ_max = 26.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −7→7
T_min = 0.451, T_max = 0.462	k = −9→9
12745 measured reflections	l = −19→19
2941 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H-atom parameters constrained
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0164P)² + 0.6492P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2941 reflections	Δρ_max = 0.44 e Å⁻³
190 parameters	Δρ_min = −0.47 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.5068 (6)	0.2375 (4)	0.4774 (2)	0.0415 (9)
O1	0.7111 (4)	0.2606 (3)	0.49106 (15)	0.0566 (7)
C2	0.3387 (6)	0.3049 (5)	0.5402 (2)	0.0460 (9)
H2	0.1897	0.3177	0.5220	0.055*
C3	0.3935 (6)	0.3475 (4)	0.6212 (2)	0.0407 (9)
H3	0.5422	0.3268	0.6369	0.049*
C11	0.5650 (5)	0.1296 (4)	0.3265 (2)	0.0341 (8)
H11	0.7103	0.1809	0.3314	0.041*
C12	0.4239 (5)	0.1438 (4)	0.3957 (2)	0.0348 (8)
C13	0.2048 (6)	0.0631 (5)	0.3885 (2)	0.0444 (9)
H13	0.1055	0.0734	0.4348	0.053*
C14	0.1380 (6)	−0.0292 (4)	0.3146 (2)	0.0454 (9)
H14	−0.0052	−0.0841	0.3118	0.055*
C15	0.2162 (6)	−0.1383 (4)	0.1639 (3)	0.0479 (10)
H15	0.0738	−0.1944	0.1591	0.057*
C16	0.3583 (7)	−0.1484 (5)	0.0960 (3)	0.0541 (11)
H16	0.3127	−0.2109	0.0451	0.065*
C17	0.5745 (7)	−0.0651 (5)	0.1018 (2)	0.0493 (10)
H17	0.6712	−0.0727	0.0546	0.059*
C18	0.6430 (6)	0.0265 (4)	0.1759 (2)	0.0403 (9)
H18	0.7867	0.0808	0.1792	0.048*
C19	0.4979 (5)	0.0400 (4)	0.2482 (2)	0.0334 (8)
C20	0.2798 (6)	−0.0440 (4)	0.2422 (2)	0.0376 (8)
C31	0.2512 (5)	0.4230 (4)	0.6895 (2)	0.0345 (8)
C32	0.3290 (5)	0.4328 (4)	0.7740 (2)	0.0398 (9)
H32	0.4694	0.3885	0.7856	0.048*
C33	0.2048 (5)	0.5061 (4)	0.8411 (2)	0.0402 (9)
H33	0.2596	0.5107	0.8973	0.048*
C34	−0.0016 (5)	0.5723 (4)	0.8236 (2)	0.0360 (8)
Br34	−0.17324 (8)	0.67362 (6)	0.91526 (3)	0.06341 (18)
C35	−0.0841 (5)	0.5658 (4)	0.7406 (2)	0.0387 (9)
H35	−0.2238	0.6115	0.7295	0.046*
C36	0.0415 (5)	0.4912 (4)	0.6743 (2)	0.0397 (9)
H36	−0.0149	0.4863	0.6183	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.041 (2)	0.049 (2)	0.036 (2)	0.0112 (19)	0.0044 (17)	0.0078 (18)
O1	0.0424 (16)	0.083 (2)	0.0434 (15)	0.0066 (14)	0.0013 (12)	−0.0014 (14)
C2	0.040 (2)	0.057 (3)	0.040 (2)	0.0099 (18)	0.0015 (17)	−0.0001 (19)
C3	0.036 (2)	0.048 (2)	0.039 (2)	0.0035 (17)	0.0025 (17)	0.0061 (18)
C11	0.0291 (18)	0.032 (2)	0.041 (2)	0.0014 (15)	0.0002 (16)	0.0047 (17)
C12	0.0329 (19)	0.039 (2)	0.033 (2)	0.0062 (16)	0.0026 (16)	0.0052 (17)
C13	0.038 (2)	0.050 (2)	0.047 (2)	0.0055 (18)	0.0140 (18)	0.013 (2)
C14	0.033 (2)	0.039 (2)	0.064 (3)	0.0000 (17)	0.0039 (19)	0.008 (2)
C15	0.042 (2)	0.035 (2)	0.066 (3)	0.0021 (17)	−0.017 (2)	−0.001 (2)
C16	0.069 (3)	0.044 (2)	0.049 (3)	0.014 (2)	−0.012 (2)	−0.005 (2)
C17	0.058 (3)	0.051 (2)	0.040 (2)	0.018 (2)	0.0063 (19)	0.003 (2)
C18	0.040 (2)	0.041 (2)	0.040 (2)	0.0052 (17)	0.0028 (17)	0.0006 (18)
C19	0.036 (2)	0.0306 (19)	0.034 (2)	0.0073 (16)	−0.0022 (16)	0.0044 (16)
C20	0.035 (2)	0.030 (2)	0.049 (2)	0.0027 (16)	−0.0056 (17)	0.0034 (18)
C31	0.0363 (19)	0.032 (2)	0.035 (2)	0.0004 (16)	0.0020 (16)	0.0039 (16)
C32	0.0321 (19)	0.045 (2)	0.043 (2)	0.0045 (16)	−0.0002 (17)	0.0077 (18)
C33	0.041 (2)	0.044 (2)	0.036 (2)	0.0011 (17)	−0.0035 (17)	0.0019 (17)
C34	0.0357 (19)	0.031 (2)	0.041 (2)	−0.0026 (16)	0.0027 (16)	0.0002 (17)
Br34	0.0648 (3)	0.0676 (3)	0.0562 (3)	0.0145 (2)	0.0149 (2)	−0.0101 (2)
C35	0.0284 (18)	0.041 (2)	0.048 (2)	0.0027 (16)	0.0000 (17)	0.0092 (18)
C36	0.038 (2)	0.046 (2)	0.035 (2)	0.0016 (17)	−0.0016 (16)	0.0061 (18)

Geometric parameters (Å, º) top

C1—O1	1.221 (4)	C16—C17	1.405 (5)
C1—C2	1.473 (5)	C16—H16	0.9300
C1—C12	1.485 (5)	C17—C18	1.359 (5)
C2—C3	1.314 (4)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.414 (4)
C3—C31	1.456 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.417 (4)
C11—C12	1.363 (4)	C31—C32	1.388 (4)
C11—C19	1.403 (4)	C31—C36	1.389 (4)
C11—H11	0.9300	C32—C33	1.375 (4)
C12—C13	1.413 (5)	C32—H32	0.9300
C13—C14	1.355 (5)	C33—C34	1.373 (4)
C13—H13	0.9300	C33—H33	0.9300
C14—C20	1.405 (5)	C34—C35	1.375 (4)
C14—H14	0.9300	C34—Br34	1.889 (3)
C15—C16	1.349 (5)	C35—C36	1.375 (4)
C15—C20	1.413 (5)	C35—H35	0.9300
C15—H15	0.9300	C36—H36	0.9300

O1—C1—C2	121.0 (3)	C16—C17—H17	119.9
O1—C1—C12	120.2 (3)	C17—C18—C19	120.6 (3)
C2—C1—C12	118.9 (3)	C17—C18—H18	119.7
C3—C2—C1	121.8 (3)	C19—C18—H18	119.7
C3—C2—H2	119.1	C11—C19—C18	122.3 (3)
C1—C2—H2	119.1	C11—C19—C20	118.7 (3)
C2—C3—C31	128.3 (3)	C18—C19—C20	119.0 (3)
C2—C3—H3	115.9	C14—C20—C15	123.4 (3)
C31—C3—H3	115.9	C14—C20—C19	118.2 (3)
C12—C11—C19	122.1 (3)	C15—C20—C19	118.4 (3)
C12—C11—H11	118.9	C32—C31—C36	117.6 (3)
C19—C11—H11	118.9	C32—C31—C3	119.3 (3)
C11—C12—C13	118.7 (3)	C36—C31—C3	123.1 (3)
C11—C12—C1	119.5 (3)	C33—C32—C31	122.0 (3)
C13—C12—C1	121.8 (3)	C33—C32—H32	119.0
C14—C13—C12	120.6 (3)	C31—C32—H32	119.0
C14—C13—H13	119.7	C34—C33—C32	118.8 (3)
C12—C13—H13	119.7	C34—C33—H33	120.6
C13—C14—C20	121.7 (3)	C32—C33—H33	120.6
C13—C14—H14	119.2	C33—C34—C35	121.0 (3)
C20—C14—H14	119.2	C33—C34—Br34	119.1 (3)
C16—C15—C20	121.2 (4)	C35—C34—Br34	119.9 (2)
C16—C15—H15	119.4	C36—C35—C34	119.5 (3)
C20—C15—H15	119.4	C36—C35—H35	120.2
C15—C16—C17	120.5 (4)	C34—C35—H35	120.2
C15—C16—H16	119.8	C35—C36—C31	121.1 (3)
C17—C16—H16	119.8	C35—C36—H36	119.4
C18—C17—C16	120.3 (3)	C31—C36—H36	119.4
C18—C17—H17	119.9

O1—C1—C2—C3	−19.8 (6)	C13—C14—C20—C19	0.3 (5)
C12—C1—C2—C3	161.6 (3)	C16—C15—C20—C14	179.8 (3)
C1—C2—C3—C31	176.8 (3)	C16—C15—C20—C19	−0.2 (5)
C19—C11—C12—C13	1.1 (5)	C11—C19—C20—C14	1.9 (4)
C19—C11—C12—C1	178.8 (3)	C18—C19—C20—C14	180.0 (3)
O1—C1—C12—C11	−19.9 (5)	C11—C19—C20—C15	−178.1 (3)
C2—C1—C12—C11	158.6 (3)	C18—C19—C20—C15	0.0 (5)
O1—C1—C12—C13	157.7 (3)	C2—C3—C31—C32	169.5 (4)
C2—C1—C12—C13	−23.7 (5)	C2—C3—C31—C36	−12.4 (6)
C11—C12—C13—C14	1.2 (5)	C36—C31—C32—C33	0.3 (5)
C1—C12—C13—C14	−176.4 (3)	C3—C31—C32—C33	178.5 (3)
C12—C13—C14—C20	−1.9 (5)	C31—C32—C33—C34	−0.4 (5)
C20—C15—C16—C17	0.1 (5)	C32—C33—C34—C35	0.1 (5)
C15—C16—C17—C18	0.1 (5)	C32—C33—C34—Br34	−179.9 (2)
C16—C17—C18—C19	−0.3 (5)	C33—C34—C35—C36	0.3 (5)
C12—C11—C19—C18	179.3 (3)	Br34—C34—C35—C36	−179.7 (2)
C12—C11—C19—C20	−2.6 (5)	C34—C35—C36—C31	−0.4 (5)
C17—C18—C19—C11	178.3 (3)	C32—C31—C36—C35	0.0 (5)
C17—C18—C19—C20	0.2 (5)	C3—C31—C36—C35	−178.0 (3)
C13—C14—C20—C15	−179.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32···Cg4ⁱ	0.93	2.85	3.513 (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

C₁₇H₁₂OS	Z = 2
M_r = 264.33	F(000) = 276
Triclinic, P1	D_x = 1.360 Mg m⁻³
a = 5.8271 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4489 (4) Å	Cell parameters from 4247 reflections
c = 15.2068 (9) Å	θ = 1.4–32.6°
α = 79.745 (3)°	µ = 0.24 mm⁻¹
β = 84.427 (3)°	T = 296 K
γ = 85.763 (3)°	Block, colourless
V = 645.36 (6) Å³	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker Kappa APEXII diffractometer	2164 reflections with I > 2σ(I)
Radiation source: fine focus sealed tube	R_int = 0.033
φ and ω scans	θ_max = 26.6°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −7→7
T_min = 0.933, T_max = 0.965	k = −9→9
18170 measured reflections	l = −19→19
2694 independent reflections

Refinement top

Refinement on F²	15 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.140	w = 1/[σ²(F_o²) + (0.0278P)² + 0.8674P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
2694 reflections	Δρ_max = 0.23 e Å⁻³
185 parameters	Δρ_min = −0.41 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.9718 (5)	0.2608 (4)	0.50120 (19)	0.0423 (7)
O1	1.1716 (4)	0.2701 (4)	0.51604 (15)	0.0639 (7)
C11	1.0710 (4)	0.3045 (3)	0.33771 (18)	0.0349 (6)
H11	1.2055	0.3543	0.3481	0.042*
C12	0.9152 (4)	0.2463 (3)	0.40887 (18)	0.0363 (6)
C13	0.7111 (5)	0.1705 (4)	0.3930 (2)	0.0430 (7)
H13	0.6026	0.1340	0.4407	0.052*
C14	0.6715 (5)	0.1503 (4)	0.3085 (2)	0.0450 (7)
H14	0.5383	0.0965	0.2997	0.054*
C15	0.7924 (5)	0.1952 (4)	0.1456 (2)	0.0477 (7)
H15	0.6608	0.1423	0.1345	0.057*
C16	0.9447 (6)	0.2570 (5)	0.0761 (2)	0.0549 (8)
H16	0.9177	0.2450	0.0182	0.066*
C17	1.1423 (6)	0.3388 (4)	0.0905 (2)	0.0507 (8)
H17	1.2449	0.3829	0.0420	0.061*
C18	1.1860 (5)	0.3546 (4)	0.17489 (19)	0.0395 (6)
H18	1.3192	0.4084	0.1836	0.047*
C19	1.0318 (4)	0.2905 (3)	0.24950 (18)	0.0343 (6)
C20	0.8275 (4)	0.2088 (3)	0.23435 (19)	0.0372 (6)
C2	0.7821 (5)	0.2641 (4)	0.57262 (19)	0.0426 (7)	0.780 (3)
H2	0.6316	0.2953	0.5577	0.051*	0.780 (3)
C3	0.8251 (5)	0.2231 (4)	0.65741 (19)	0.0406 (6)	0.780 (3)
H3	0.9761	0.1831	0.6687	0.049*	0.780 (3)
C32	0.6634 (4)	0.2334 (3)	0.73499 (18)	0.0368 (6)	0.780 (3)
S31	0.3958 (2)	0.33969 (18)	0.72951 (8)	0.0440 (3)	0.780 (3)
C33	0.7012 (11)	0.1705 (10)	0.8224 (4)	0.0429 (13)	0.780 (3)
H33	0.8370	0.1056	0.8395	0.051*	0.780 (3)
C34	0.5200 (8)	0.2109 (16)	0.8849 (3)	0.0480 (13)	0.780 (3)
H34	0.5217	0.1784	0.9468	0.058*	0.780 (3)
C35	0.3430 (8)	0.3035 (10)	0.8425 (3)	0.0471 (12)	0.780 (3)
H35	0.2067	0.3431	0.8721	0.057*	0.780 (3)
C2A	0.7821 (5)	0.2641 (4)	0.57262 (19)	0.0426 (7)	0.220 (3)
H2A	0.6316	0.2953	0.5577	0.051*	0.220 (3)
C3A	0.8251 (5)	0.2231 (4)	0.65741 (19)	0.0406 (6)	0.220 (3)
H3A	0.9761	0.1831	0.6687	0.049*	0.220 (3)
C42	0.6634 (4)	0.2334 (3)	0.73499 (18)	0.0368 (6)	0.220 (3)
S41	0.7334 (11)	0.1491 (11)	0.8392 (3)	0.0440 (3)	0.220 (3)
C43	0.4393 (19)	0.299 (3)	0.7365 (8)	0.0440 (3)	0.220 (3)
H43	0.3681	0.3486	0.6847	0.053*	0.220 (3)
C44	0.324 (2)	0.287 (4)	0.8227 (9)	0.0471 (12)	0.220 (3)
H44	0.1725	0.3285	0.8352	0.057*	0.220 (3)
C45	0.467 (3)	0.205 (6)	0.8851 (8)	0.0480 (13)	0.220 (3)
H45	0.4230	0.1821	0.9463	0.058*	0.220 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0371 (15)	0.0436 (16)	0.0433 (16)	−0.0010 (12)	−0.0020 (12)	−0.0009 (12)
O1	0.0390 (12)	0.103 (2)	0.0475 (13)	−0.0079 (12)	−0.0034 (10)	−0.0067 (13)
C11	0.0281 (12)	0.0329 (13)	0.0441 (15)	−0.0036 (10)	−0.0003 (11)	−0.0084 (11)
C12	0.0326 (13)	0.0319 (13)	0.0430 (15)	0.0007 (10)	−0.0003 (11)	−0.0051 (11)
C13	0.0337 (14)	0.0387 (15)	0.0532 (18)	−0.0063 (11)	0.0049 (12)	−0.0018 (13)
C14	0.0321 (14)	0.0387 (15)	0.067 (2)	−0.0068 (12)	−0.0059 (13)	−0.0144 (14)
C15	0.0404 (16)	0.0443 (17)	0.064 (2)	0.0020 (13)	−0.0166 (14)	−0.0191 (15)
C16	0.058 (2)	0.060 (2)	0.0501 (19)	0.0077 (16)	−0.0144 (15)	−0.0189 (16)
C17	0.0536 (18)	0.0493 (18)	0.0467 (18)	0.0039 (14)	0.0027 (14)	−0.0077 (14)
C18	0.0372 (14)	0.0366 (14)	0.0443 (16)	−0.0015 (11)	−0.0028 (12)	−0.0065 (12)
C19	0.0299 (12)	0.0274 (12)	0.0444 (15)	0.0034 (10)	−0.0032 (11)	−0.0051 (11)
C20	0.0331 (13)	0.0291 (13)	0.0497 (16)	0.0041 (10)	−0.0043 (11)	−0.0095 (11)
C2	0.0357 (14)	0.0468 (16)	0.0445 (16)	0.0018 (12)	−0.0035 (12)	−0.0072 (13)
C3	0.0340 (14)	0.0381 (15)	0.0494 (17)	−0.0011 (11)	0.0004 (12)	−0.0096 (12)
C32	0.0355 (14)	0.0326 (13)	0.0439 (15)	−0.0065 (11)	−0.0021 (11)	−0.0096 (11)
S31	0.0347 (6)	0.0467 (8)	0.0509 (6)	0.0066 (4)	−0.0080 (4)	−0.0109 (4)
C33	0.044 (3)	0.041 (3)	0.043 (3)	0.005 (2)	−0.020 (2)	0.000 (2)
C34	0.057 (3)	0.047 (2)	0.0410 (17)	−0.015 (4)	0.0007 (17)	−0.0066 (14)
C35	0.0433 (18)	0.047 (2)	0.056 (3)	−0.0085 (17)	0.0066 (18)	−0.025 (2)
C2A	0.0357 (14)	0.0468 (16)	0.0445 (16)	0.0018 (12)	−0.0035 (12)	−0.0072 (13)
C3A	0.0340 (14)	0.0381 (15)	0.0494 (17)	−0.0011 (11)	0.0004 (12)	−0.0096 (12)
C42	0.0355 (14)	0.0326 (13)	0.0439 (15)	−0.0065 (11)	−0.0021 (11)	−0.0096 (11)
S41	0.0347 (6)	0.0467 (8)	0.0509 (6)	0.0066 (4)	−0.0080 (4)	−0.0109 (4)
C43	0.0347 (6)	0.0467 (8)	0.0509 (6)	0.0066 (4)	−0.0080 (4)	−0.0109 (4)
C44	0.0433 (18)	0.047 (2)	0.056 (3)	−0.0085 (17)	0.0066 (18)	−0.025 (2)
C45	0.057 (3)	0.047 (2)	0.0410 (17)	−0.015 (4)	0.0007 (17)	−0.0066 (14)

Geometric parameters (Å, º) top

C1—O1	1.217 (3)	C19—C20	1.432 (4)
C1—C2	1.474 (4)	C2—C3	1.315 (4)
C1—C12	1.497 (4)	C2—H2	0.9300
C11—C12	1.372 (4)	C3—C32	1.446 (4)
C11—C19	1.405 (4)	C3—H3	0.9300
C11—H11	0.9300	C32—C33	1.363 (6)
C12—C13	1.413 (4)	C32—S31	1.698 (2)
C13—C14	1.364 (4)	S31—C35	1.692 (5)
C13—H13	0.9300	C33—C34	1.403 (7)
C14—C20	1.404 (4)	C33—H33	0.9300
C14—H14	0.9300	C34—C35	1.350 (5)
C15—C16	1.350 (5)	C34—H34	0.9300
C15—C20	1.407 (4)	C35—H35	0.9300
C15—H15	0.9300	S41—C45	1.695 (7)
C16—C17	1.395 (5)	C43—C44	1.404 (9)
C16—H16	0.9300	C43—H43	0.9300
C17—C18	1.359 (4)	C44—C45	1.352 (7)
C17—H17	0.9300	C44—H44	0.9300
C18—C19	1.413 (4)	C45—H45	0.9300
C18—H18	0.9300

O1—C1—C2	121.2 (3)	C14—C20—C15	123.7 (3)
O1—C1—C12	119.8 (3)	C14—C20—C19	118.3 (3)
C2—C1—C12	118.9 (2)	C15—C20—C19	118.0 (3)
C12—C11—C19	121.5 (2)	C3—C2—C1	120.2 (3)
C12—C11—H11	119.3	C3—C2—H2	119.9
C19—C11—H11	119.3	C1—C2—H2	119.9
C11—C12—C13	119.2 (3)	C2—C3—C32	127.2 (2)
C11—C12—C1	118.5 (2)	C2—C3—H3	116.4
C13—C12—C1	122.3 (2)	C32—C3—H3	116.4
C14—C13—C12	120.6 (3)	C33—C32—C3	126.9 (3)
C14—C13—H13	119.7	C33—C32—S31	109.4 (3)
C12—C13—H13	119.7	C3—C32—S31	123.67 (19)
C13—C14—C20	121.4 (3)	C35—S31—C32	92.48 (19)
C13—C14—H14	119.3	C32—C33—C34	115.0 (5)
C20—C14—H14	119.3	C32—C33—H33	122.5
C16—C15—C20	121.7 (3)	C34—C33—H33	122.5
C16—C15—H15	119.1	C35—C34—C33	110.4 (5)
C20—C15—H15	119.1	C35—C34—H34	124.8
C15—C16—C17	120.4 (3)	C33—C34—H34	124.8
C15—C16—H16	119.8	C34—C35—S31	112.7 (4)
C17—C16—H16	119.8	C34—C35—H35	123.6
C18—C17—C16	120.4 (3)	S31—C35—H35	123.6
C18—C17—H17	119.8	C44—C43—H43	122.8
C16—C17—H17	119.8	C45—C44—C43	110.2 (8)
C17—C18—C19	120.9 (3)	C45—C44—H44	124.9
C17—C18—H18	119.6	C43—C44—H44	124.9
C19—C18—H18	119.6	C44—C45—S41	112.5 (7)
C11—C19—C18	122.5 (2)	C44—C45—H45	123.8
C11—C19—C20	118.9 (2)	S41—C45—H45	123.8
C18—C19—C20	118.6 (3)

C19—C11—C12—C13	0.1 (4)	C16—C15—C20—C19	−0.2 (4)
C19—C11—C12—C1	178.3 (2)	C11—C19—C20—C14	1.6 (4)
O1—C1—C12—C11	−21.7 (4)	C18—C19—C20—C14	−178.1 (2)
C2—C1—C12—C11	158.1 (3)	C11—C19—C20—C15	−179.6 (2)
O1—C1—C12—C13	156.5 (3)	C18—C19—C20—C15	0.6 (4)
C2—C1—C12—C13	−23.7 (4)	O1—C1—C2—C3	−20.2 (5)
C11—C12—C13—C14	1.8 (4)	C12—C1—C2—C3	160.0 (3)
C1—C12—C13—C14	−176.3 (3)	C1—C2—C3—C32	174.8 (3)
C12—C13—C14—C20	−2.0 (4)	C2—C3—C32—C33	171.5 (5)
C20—C15—C16—C17	−0.7 (5)	C2—C3—C32—S31	−12.1 (4)
C15—C16—C17—C18	1.1 (5)	C33—C32—S31—C35	1.4 (4)
C16—C17—C18—C19	−0.6 (4)	C3—C32—S31—C35	−175.6 (3)
C12—C11—C19—C18	178.0 (2)	C3—C32—C33—C34	175.3 (6)
C12—C11—C19—C20	−1.8 (4)	S31—C32—C33—C34	−1.5 (8)
C17—C18—C19—C11	−180.0 (3)	C32—C33—C34—C35	0.9 (11)
C17—C18—C19—C20	−0.2 (4)	C33—C34—C35—S31	0.2 (10)
C13—C14—C20—C15	−178.4 (3)	C32—S31—C35—C34	−0.9 (6)
C13—C14—C20—C19	0.3 (4)	C43—C44—C45—S41	1 (4)
C16—C15—C20—C14	178.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···Cg5ⁱ	0.93	2.80	3.572 (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 =	1	2	nil	nil
Cx2—Cx1—Cx12—Cx11	155.7 (2)	151.6 (2)	158.6 (3)	158.1 (3)
Cx2—Cx3—Cx31—Cx32	169.7 (2)	167.2 (2)	169.5 (4)
Cx2—Cx3—Cx32—Cx33				171.1 (5)
Cx2—Cx3—Cx32—Sx41				171.3 (4)

Hydrogen-bond parameters (Å, °) for compounds (I)–(III) top

Compound	D—H···A	D—H	H···A	D···A	D—H···A
(I)	C132—H132···Cg1ⁱ	0.93	2.88	3.557 (3)	131
	C135—H135···Cg2ⁱⁱ	0.93	2.83	3.503 (3)	130
	C214—H214···Cg3ⁱⁱ	0.93	2.87	3.554 (2)	131

(II)	C32—H32···Cg4ⁱⁱⁱ	0.93	2.85	3.513 (3)	129

(III)	C18—H18···Cg5^iv	0.93	2.80	3.572 (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···Cg		C—Br	Br···Cg	C···Cg	C—Br···Cg
C34—Br34···Cg4ⁱⁱ		1.889 (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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Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supra­moleular assembly mediated by C—Hπ and C—Brπ inter­actions

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Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—Hπ and C—Brπ interactions