Peculiarities of supra­molecular organization of cyclic ketones with vinyl­acetyl­ene fragments

1,5-Diar­yl(heteroar­yl)pentenynones show a tendency to crystallize in acentric space groups due to their inclination to form C—H...O hydrogen-bonded chains instead of dimers and thus exhibit nonlinear optical properties. A series of symmetrical α,α′-bis­(3-aryl­prop-2-yn-1-yl­idene)cyclo­alkanones and unsymmetrical α-(furan-2-yl­methyl­ene)-α′-(3-aryl­prop-2-yn-1-yl­idene)cyclo­hexa­nones closely related to pentenynones was synthesized, namely 2,5-bis­(3-phenyl­prop-2-yn-1-yl­idene)cyclo­penta­none, C₂₃H₁₆O, 2,5-bis­[3-(4-bromo­phen­yl)prop-2-yn-1-yl­idene]cyclo­penta­none, C₂₃H₁₄Br₂O, 2,6-bis­(3-phenyl­prop-2-yn-1-yl­idene)cyclo­hexa­none, C₂₄H₁₈O, 2,6-bis­[3-(4-bromo­phen­yl)prop-2-yn-1-yl­idene]cyclo­hexa­none, C₂₄H₁₆Br₂O, 4-tert-butyl-2,6-bis­(3-phenyl­prop-2-yn-1-yl­idene)cyclo­hexa­none, C₂₈H₂₅O, 4-tert-butyl-2,6-bis­[3-(4-methyl­phen­yl)prop-2-yn-1-yl­idene]cyclo­hexa­none, C₃₀H₃₀O, 2-(furan-2-yl­methyl­ene)-6-(3-phenyl­prop-2-yn-1-yl­idene)cyclo­hexa­none, C₂₀H₁₆O₂, and 6-(3-butyl­prop-2-yn-1-yl­idene)-2-(furan-2-yl­methyl­ene)cyclo­hexa­none, C₁₀H₂₀O₂, and investigated by means of X-ray diffraction to understand peculiarities of their supra­molecular organization. Four of the eight novel compounds crystallize in acentric space groups. Three of these four compounds contain substituents at the para position of the phenyl ring, which affect the charge density on the H(C_Ph) atoms and thus stabilize C_Ph—H...O inter­actions. The fourth compound realizes the C—H...O hydrogen bonding via H atoms of the furyl ring. The applicability and shortcomings of the Full Inter­action Map tool to predict the likelihood of C—H...O and C—H...Br hydrogen-bonded motifs, and the effect of substituents on the phenyl ring on the supra­molecular architecture are discussed.

Computing details

Data collection: APEX (Bruker, 2010) for (3a), (3b), (3c), (3e), (5b). Cell refinement: SAINT (Bruker, 2010) for (3a), (3b), (3c), (3e), (5b). Data reduction: SAINT (Bruker, 2010) for (3a), (3b), (3c), (3e), (5b). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (3a), (3f); SHELXT (Sheldrick, 2015a) for (3b), (3c), (3d), (3e), (5b); SHELXXS97 (Sheldrick, 2008) for (5a). Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) for (3a), (3b), (3c), (3d), (3e), (5a), (5b); XLMP (Sheldrick, 2008) for (3f). For all structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2,5-Bis(3-phenylprop-2-yn-1-ylidene)cyclopentanone (3a)

Crystal data

C23H16O	F(000) = 648
Mr = 308.36	Dx = 1.202 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.723 (6) Å	Cell parameters from 2200 reflections
b = 27.11 (3) Å	θ = 2.4–29.3°
c = 10.984 (12) Å	µ = 0.07 mm^−1
β = 89.55 (3)°	T = 200 K
V = 1704 (3) Å^3	Plate, light brown
Z = 4	0.42 × 0.18 × 0.04 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer	2173 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.203
phi and ω scans	θmax = 30.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −7→7
Tmin = 0.459, Tmax = 0.746	k = −38→37
18018 measured reflections	l = −14→14
4776 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.084	H-atom parameters constrained
wR(F^2) = 0.191	w = 1/[σ^2(Fo^2) + (0.055P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4776 reflections	Δρmax = 0.26 e Å^−3
217 parameters	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2923 (3)	0.40975 (7)	0.93814 (16)	0.0546 (5)
C1	0.3399 (4)	0.39016 (9)	0.8400 (2)	0.0399 (6)
C2	0.5325 (4)	0.35511 (9)	0.8183 (2)	0.0391 (6)
C3	0.5241 (4)	0.33729 (10)	0.6890 (2)	0.0465 (6)
H3A	0.4942	0.3013	0.6865	0.056*
H3B	0.6741	0.3441	0.6467	0.056*
C4	0.3234 (5)	0.36565 (13)	0.6278 (3)	0.0628 (8)
H4A	0.3842	0.3864	0.5606	0.075*
H4B	0.2069	0.3424	0.5945	0.075*
C5	0.2150 (4)	0.39702 (9)	0.7248 (2)	0.0401 (6)
C6	0.6908 (4)	0.34281 (9)	0.9030 (2)	0.0456 (6)
H6	0.6822	0.3582	0.9805	0.055*
C7	0.8692 (4)	0.30784 (10)	0.8810 (2)	0.0453 (6)
C8	1.0121 (4)	0.27709 (10)	0.8562 (2)	0.0456 (6)
C9	1.1707 (4)	0.23891 (9)	0.8201 (2)	0.0420 (6)
C10	1.3658 (4)	0.22711 (10)	0.8903 (3)	0.0503 (7)
H10	1.3928	0.2441	0.9646	0.060*
C11	1.5189 (5)	0.19091 (11)	0.8520 (3)	0.0605 (8)
H11	1.6515	0.1830	0.8996	0.073*
C12	1.4789 (5)	0.16640 (11)	0.7448 (3)	0.0637 (8)
H12	1.5847	0.1415	0.7185	0.076*
C13	1.2865 (5)	0.17754 (11)	0.6746 (3)	0.0620 (8)
H13	1.2598	0.1601	0.6011	0.074*
C14	1.1343 (4)	0.21375 (10)	0.7112 (3)	0.0539 (7)
H14	1.0035	0.2217	0.6622	0.065*
C15	0.0336 (4)	0.42770 (9)	0.7106 (2)	0.0462 (6)
H15	−0.0256	0.4450	0.7795	0.055*
C16	−0.0728 (4)	0.43521 (9)	0.5962 (3)	0.0454 (6)
C17	−0.1442 (4)	0.44076 (9)	0.4942 (3)	0.0452 (6)
C18	−0.2073 (4)	0.44766 (9)	0.3686 (2)	0.0411 (6)
C19	−0.0521 (4)	0.43317 (10)	0.2787 (3)	0.0503 (7)
H19	0.0906	0.4177	0.3005	0.060*
C20	−0.1031 (5)	0.44101 (11)	0.1563 (3)	0.0594 (8)
H20	0.0051	0.4314	0.0948	0.071*
C21	−0.3104 (5)	0.46277 (11)	0.1255 (3)	0.0573 (8)
H21	−0.3454	0.4682	0.0421	0.069*
C22	−0.4666 (4)	0.47669 (10)	0.2128 (3)	0.0553 (7)
H22	−0.6100	0.4916	0.1899	0.066*
C23	−0.4185 (4)	0.46941 (10)	0.3345 (3)	0.0488 (7)
H23	−0.5287	0.4792	0.3950	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0676 (11)	0.0593 (12)	0.0370 (11)	0.0160 (9)	−0.0094 (8)	−0.0083 (9)
C1	0.0442 (13)	0.0405 (14)	0.0350 (14)	−0.0017 (11)	0.0011 (11)	−0.0018 (11)
C2	0.0393 (12)	0.0397 (14)	0.0385 (14)	−0.0018 (11)	−0.0056 (11)	−0.0005 (11)
C3	0.0496 (13)	0.0512 (16)	0.0386 (15)	0.0019 (12)	−0.0051 (11)	−0.0030 (12)
C4	0.0601 (16)	0.088 (2)	0.0401 (16)	0.0195 (16)	−0.0116 (13)	−0.0083 (16)
C5	0.0421 (12)	0.0454 (14)	0.0328 (13)	−0.0017 (11)	−0.0069 (10)	0.0012 (11)
C6	0.0489 (13)	0.0464 (15)	0.0416 (15)	0.0023 (12)	−0.0082 (12)	−0.0032 (12)
C7	0.0421 (13)	0.0522 (16)	0.0419 (15)	0.0009 (13)	−0.0100 (11)	0.0008 (13)
C8	0.0422 (13)	0.0509 (16)	0.0438 (15)	−0.0028 (13)	−0.0092 (11)	0.0034 (13)
C9	0.0432 (13)	0.0407 (14)	0.0422 (15)	−0.0032 (11)	−0.0009 (11)	0.0048 (12)
C10	0.0527 (15)	0.0538 (17)	0.0445 (16)	0.0018 (13)	−0.0045 (12)	0.0050 (13)
C11	0.0592 (16)	0.0630 (19)	0.059 (2)	0.0146 (15)	0.0024 (14)	0.0166 (16)
C12	0.0734 (19)	0.0492 (18)	0.068 (2)	0.0116 (15)	0.0148 (17)	0.0068 (16)
C13	0.0739 (19)	0.0573 (18)	0.0546 (19)	−0.0060 (16)	0.0033 (16)	−0.0134 (15)
C14	0.0528 (15)	0.0570 (17)	0.0520 (18)	−0.0025 (14)	−0.0049 (13)	−0.0069 (14)
C15	0.0502 (14)	0.0456 (15)	0.0430 (16)	0.0017 (12)	−0.0098 (11)	−0.0019 (12)
C16	0.0483 (14)	0.0418 (15)	0.0462 (17)	0.0036 (11)	−0.0151 (12)	0.0012 (12)
C17	0.0434 (13)	0.0420 (14)	0.0505 (17)	0.0018 (11)	−0.0138 (12)	−0.0003 (13)
C18	0.0379 (12)	0.0403 (14)	0.0453 (16)	−0.0031 (11)	−0.0139 (11)	−0.0014 (12)
C19	0.0396 (13)	0.0560 (17)	0.0555 (18)	0.0008 (12)	−0.0102 (12)	−0.0050 (14)
C20	0.0580 (17)	0.069 (2)	0.0512 (19)	−0.0082 (15)	0.0041 (14)	−0.0093 (16)
C21	0.0654 (18)	0.0654 (19)	0.0413 (16)	−0.0139 (15)	−0.0199 (14)	0.0037 (15)
C22	0.0502 (15)	0.0617 (19)	0.0545 (19)	0.0036 (14)	−0.0229 (14)	0.0064 (15)
C23	0.0409 (13)	0.0570 (17)	0.0486 (16)	0.0036 (12)	−0.0106 (11)	−0.0035 (14)

Geometric parameters (Å, º)

O1—C1	1.230 (3)	C11—C12	1.373 (4)
C1—C2	1.473 (3)	C12—H12	0.9500
C1—C5	1.471 (4)	C12—C13	1.382 (4)
C2—C3	1.501 (4)	C13—H13	0.9500
C2—C6	1.345 (3)	C13—C14	1.371 (4)
C3—H3A	0.9900	C14—H14	0.9500
C3—H3B	0.9900	C15—H15	0.9500
C3—C4	1.541 (4)	C15—C16	1.415 (4)
C4—H4A	0.9900	C16—C17	1.204 (4)
C4—H4B	0.9900	C17—C18	1.442 (4)
C4—C5	1.494 (4)	C18—C19	1.379 (4)
C5—C15	1.341 (3)	C18—C23	1.398 (3)
C6—H6	0.9500	C19—H19	0.9500
C6—C7	1.413 (4)	C19—C20	1.394 (4)
C7—C8	1.198 (3)	C20—H20	0.9500
C8—C9	1.430 (4)	C20—C21	1.370 (4)
C9—C10	1.399 (4)	C21—H21	0.9500
C9—C14	1.394 (4)	C21—C22	1.359 (4)
C10—H10	0.9500	C22—H22	0.9500
C10—C11	1.379 (4)	C22—C23	1.381 (4)
C11—H11	0.9500	C23—H23	0.9500
O1—C1—C2	125.5 (2)	C12—C11—H11	120.1
O1—C1—C5	126.4 (2)	C11—C12—H12	119.6
C5—C1—C2	108.1 (2)	C11—C12—C13	120.8 (3)
C1—C2—C3	109.3 (2)	C13—C12—H12	119.6
C6—C2—C1	123.7 (2)	C12—C13—H13	120.0
C6—C2—C3	126.9 (2)	C14—C13—C12	120.0 (3)
C2—C3—H3A	110.5	C14—C13—H13	120.0
C2—C3—H3B	110.5	C9—C14—H14	119.9
C2—C3—C4	106.4 (2)	C13—C14—C9	120.2 (3)
H3A—C3—H3B	108.6	C13—C14—H14	119.9
C4—C3—H3A	110.5	C5—C15—H15	118.9
C4—C3—H3B	110.5	C5—C15—C16	122.1 (2)
C3—C4—H4A	110.5	C16—C15—H15	118.9
C3—C4—H4B	110.5	C17—C16—C15	174.2 (3)
H4A—C4—H4B	108.7	C16—C17—C18	174.7 (3)
C5—C4—C3	106.2 (2)	C19—C18—C17	118.9 (2)
C5—C4—H4A	110.5	C19—C18—C23	118.8 (3)
C5—C4—H4B	110.5	C23—C18—C17	122.3 (2)
C1—C5—C4	109.9 (2)	C18—C19—H19	119.7
C15—C5—C1	124.1 (2)	C18—C19—C20	120.5 (2)
C15—C5—C4	126.0 (2)	C20—C19—H19	119.7
C2—C6—H6	118.7	C19—C20—H20	120.2
C2—C6—C7	122.5 (2)	C21—C20—C19	119.5 (3)
C7—C6—H6	118.7	C21—C20—H20	120.2
C8—C7—C6	175.8 (3)	C20—C21—H21	119.6
C7—C8—C9	175.7 (3)	C22—C21—C20	120.7 (3)
C10—C9—C8	121.3 (2)	C22—C21—H21	119.6
C14—C9—C8	119.5 (2)	C21—C22—H22	119.7
C14—C9—C10	119.1 (2)	C21—C22—C23	120.6 (3)
C9—C10—H10	119.9	C23—C22—H22	119.7
C11—C10—C9	120.2 (3)	C18—C23—H23	120.0
C11—C10—H10	119.9	C22—C23—C18	119.9 (3)
C10—C11—H11	120.1	C22—C23—H23	120.0
C12—C11—C10	119.7 (3)
O1—C1—C2—C3	176.7 (2)	C8—C9—C10—C11	−178.5 (2)
O1—C1—C2—C6	−4.7 (4)	C8—C9—C14—C13	179.1 (2)
O1—C1—C5—C4	−178.4 (2)	C9—C10—C11—C12	−0.1 (4)
O1—C1—C5—C15	2.6 (4)	C10—C9—C14—C13	0.8 (4)
C1—C2—C3—C4	3.4 (3)	C10—C11—C12—C13	−0.1 (4)
C1—C2—C6—C7	177.8 (2)	C11—C12—C13—C14	0.7 (4)
C1—C5—C15—C16	176.3 (2)	C12—C13—C14—C9	−1.0 (4)
C2—C1—C5—C4	1.1 (3)	C14—C9—C10—C11	−0.2 (4)
C2—C1—C5—C15	−178.0 (2)	C17—C18—C19—C20	−177.5 (2)
C2—C3—C4—C5	−2.7 (3)	C17—C18—C23—C22	177.7 (2)
C3—C2—C6—C7	−3.7 (4)	C18—C19—C20—C21	−0.8 (4)
C3—C4—C5—C1	1.0 (3)	C19—C18—C23—C22	−1.0 (4)
C3—C4—C5—C15	−180.0 (2)	C19—C20—C21—C22	−0.1 (4)
C4—C5—C15—C16	−2.6 (4)	C20—C21—C22—C23	0.4 (4)
C5—C1—C2—C3	−2.8 (3)	C21—C22—C23—C18	0.2 (4)
C5—C1—C2—C6	175.9 (2)	C23—C18—C19—C20	1.3 (4)
C6—C2—C3—C4	−175.2 (2)

2,5-Bis[3-(4-bromophenyl)prop-2-yn-1-ylidene]cyclopentanone (3b)

Crystal data

C23H14Br2O	Dx = 1.665 Mg m^−3
Mr = 466.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Abm2	Cell parameters from 6354 reflections
a = 7.098 (3) Å	θ = 2–31°
b = 42.72 (2) Å	µ = 4.37 mm^−1
c = 6.135 (3) Å	T = 120 K
V = 1860.1 (15) Å^3	Needle, yellow
Z = 4	0.1 × 0.08 × 0.07 mm
F(000) = 920

Data collection

Bruker SMART APEX CCD area detector diffractometer	1928 reflections with I > 2σ(I)
phi and ω scans	Rint = 0.088
Absorption correction: multi-scan (SADABS; Bruker, 2015)	θmax = 30.5°, θmin = 1.9°
Tmin = 0.664, Tmax = 0.737	h = −10→10
9371 measured reflections	k = −59→60
2642 independent reflections	l = −8→7

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.064	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.165	(Δ/σ)max = 0.001
S = 0.97	Δρmax = 1.93 e Å^−3
2642 reflections	Δρmin = −1.09 e Å^−3
121 parameters	Absolute structure: Flack x determined using 608 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.30 (2)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br2	0.20037 (10)	0.52932 (2)	−0.27597 (19)	0.0254 (2)
C20	0.1758 (11)	0.5942 (2)	−0.1799 (16)	0.0211 (17)
H20	0.1250	0.5963	−0.3225	0.025*
C19	0.2287 (12)	0.56488 (19)	−0.0978 (15)	0.0180 (16)
C9	0.2839 (11)	0.6441 (2)	0.3037 (16)	0.0215 (17)
C16	0.2694 (11)	0.61730 (19)	0.1658 (13)	0.0181 (17)
C21	0.2001 (11)	0.62021 (19)	−0.0451 (15)	0.0195 (16)
H21	0.1686	0.6404	−0.0988	0.023*
C17	0.3224 (9)	0.58749 (17)	0.2436 (18)	0.0176 (15)
H17	0.3737	0.5853	0.3858	0.021*
C7	0.3169 (12)	0.6929 (2)	0.5574 (14)	0.0191 (16)
H7	0.3678	0.6905	0.6997	0.023*
C18	0.2993 (11)	0.56113 (19)	0.1114 (14)	0.0192 (15)
H18	0.3315	0.5409	0.1640	0.023*
C8	0.2953 (13)	0.6661 (2)	0.4269 (17)	0.0252 (19)
O1	0.3698 (13)	0.7500	0.8151 (15)	0.022 (2)
C5	0.3090 (15)	0.7500	0.626 (2)	0.014 (2)
C6	0.2691 (11)	0.7219 (2)	0.4905 (15)	0.0177 (15)
C23	0.1891 (13)	0.7318 (2)	0.2744 (12)	0.026 (2)
H23A	0.0593	0.7237	0.2567	0.031*
H23B	0.2676	0.7237	0.1535	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br2	0.0244 (4)	0.0226 (4)	0.0291 (4)	−0.0021 (3)	−0.0013 (6)	−0.0085 (5)
C20	0.015 (4)	0.029 (4)	0.019 (4)	−0.004 (3)	−0.003 (3)	0.002 (3)
C19	0.015 (4)	0.021 (4)	0.017 (4)	0.003 (3)	0.007 (3)	0.000 (3)
C9	0.018 (4)	0.024 (4)	0.023 (4)	0.000 (3)	0.004 (3)	0.003 (3)
C16	0.014 (3)	0.022 (4)	0.018 (4)	−0.007 (3)	0.007 (3)	0.000 (3)
C21	0.015 (4)	0.020 (4)	0.024 (4)	−0.001 (3)	0.005 (3)	0.003 (3)
C17	0.016 (3)	0.025 (3)	0.012 (4)	0.001 (2)	−0.001 (3)	0.000 (4)
C7	0.019 (4)	0.026 (4)	0.013 (4)	0.001 (3)	0.002 (3)	−0.002 (3)
C18	0.019 (4)	0.019 (3)	0.019 (4)	−0.001 (3)	0.000 (3)	0.000 (3)
C8	0.026 (5)	0.023 (4)	0.027 (5)	0.001 (4)	−0.001 (4)	0.002 (3)
O1	0.017 (5)	0.033 (5)	0.015 (4)	0.000	−0.001 (4)	0.000
C5	0.007 (5)	0.020 (5)	0.014 (5)	0.000	0.005 (4)	0.000
C6	0.016 (3)	0.027 (4)	0.010 (4)	−0.006 (3)	−0.002 (3)	0.001 (3)
C23	0.039 (5)	0.032 (4)	0.007 (4)	−0.002 (4)	−0.005 (3)	0.000 (3)

Geometric parameters (Å, º)

Br2—C19	1.882 (8)	C7—H7	0.9500
C20—H20	0.9500	C7—C8	1.406 (12)
C20—C19	1.400 (12)	C7—C6	1.346 (12)
C20—C21	1.397 (12)	C18—H18	0.9500
C19—C18	1.387 (12)	O1—C5	1.237 (14)
C9—C16	1.427 (12)	C5—C6	1.489 (12)
C9—C8	1.209 (13)	C5—C6^i	1.489 (12)
C16—C21	1.390 (12)	C6—C23	1.503 (12)
C16—C17	1.411 (11)	C23—C23^i	1.556 (18)
C21—H21	0.9500	C23—H23A	0.9900
C17—H17	0.9500	C23—H23B	0.9900
C17—C18	1.398 (12)
C19—C20—H20	121.1	C6—C7—C8	123.2 (8)
C21—C20—H20	121.1	C19—C18—C17	119.1 (8)
C21—C20—C19	117.7 (8)	C19—C18—H18	120.4
C20—C19—Br2	118.9 (7)	C17—C18—H18	120.4
C18—C19—Br2	118.9 (6)	C9—C8—C7	175.5 (10)
C18—C19—C20	122.2 (8)	O1—C5—C6^i	126.1 (6)
C8—C9—C16	177.7 (10)	O1—C5—C6	126.1 (6)
C21—C16—C9	120.4 (8)	C6—C5—C6^i	107.7 (11)
C21—C16—C17	119.3 (8)	C7—C6—C5	121.6 (8)
C17—C16—C9	120.3 (8)	C7—C6—C23	128.5 (8)
C20—C21—H21	119.2	C5—C6—C23	109.7 (8)
C16—C21—C20	121.6 (8)	C6—C23—C23^i	106.4 (5)
C16—C21—H21	119.2	C6—C23—H23A	110.5
C16—C17—H17	120.0	C6—C23—H23B	110.5
C18—C17—C16	120.0 (9)	C23^i—C23—H23A	110.5
C18—C17—H17	120.0	C23^i—C23—H23B	110.5
C8—C7—H7	118.4	H23A—C23—H23B	108.6
C6—C7—H7	118.4

Symmetry code: (i) x, −y+3/2, z.

2,6-Bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone (3c)

Crystal data

C24H18O	F(000) = 680
Mr = 322.38	Dx = 1.231 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.498 (4) Å	Cell parameters from 160 reflections
b = 27.52 (2) Å	θ = 3.5–19.9°
c = 13.885 (9) Å	µ = 0.07 mm^−1
β = 124.09 (3)°	T = 120 K
V = 1740 (2) Å^3	Needle, orange
Z = 4	0.5 × 0.01 × 0.01 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer	2379 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.250
phi and ω scans	θmax = 30.8°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2015)	h = −7→7
Tmin = 0.549, Tmax = 0.892	k = −39→39
31410 measured reflections	l = −19→19
5336 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.085	H-atom parameters constrained
wR(F^2) = 0.131	w = 1/[σ^2(Fo^2) + (0.010P)^2 + 0.2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5336 reflections	Δρmax = 0.35 e Å^−3
226 parameters	Δρmin = −0.29 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.2215 (3)	0.38803 (5)	0.43170 (12)	0.0283 (4)
C1	−0.0203 (5)	0.49168 (8)	0.69236 (19)	0.0253 (5)
C2	0.0487 (5)	0.46686 (8)	0.64072 (19)	0.0255 (5)
C3	0.1269 (5)	0.43898 (8)	0.57618 (19)	0.0246 (5)
H3	0.0025	0.4413	0.4938	0.030*
C4	0.3596 (5)	0.40976 (7)	0.62070 (18)	0.0215 (5)
C5	0.3993 (5)	0.38318 (7)	0.53697 (18)	0.0213 (5)
C6	0.6545 (4)	0.35037 (7)	0.58313 (18)	0.0208 (5)
C7	0.6980 (5)	0.32912 (8)	0.50745 (18)	0.0242 (5)
H7	0.5634	0.3365	0.4274	0.029*
C8	0.9293 (5)	0.29653 (8)	0.53765 (18)	0.0256 (5)
C9	1.1210 (5)	0.26811 (8)	0.56295 (18)	0.0260 (5)
C10	−0.0992 (5)	0.52097 (8)	0.75603 (19)	0.0245 (5)
C11	−0.3717 (5)	0.54333 (8)	0.7005 (2)	0.0289 (6)
H11	−0.5068	0.5396	0.6189	0.035*
C12	−0.4488 (5)	0.57078 (8)	0.7620 (2)	0.0350 (6)
H12	−0.6372	0.5856	0.7230	0.042*
C13	−0.2541 (6)	0.57689 (9)	0.8797 (2)	0.0408 (7)
H13	−0.3068	0.5963	0.9219	0.049*
C14	0.0170 (6)	0.55503 (10)	0.9364 (2)	0.0468 (7)
H14	0.1506	0.5591	1.0180	0.056*
C15	0.0961 (6)	0.52717 (9)	0.8753 (2)	0.0387 (7)
H15	0.2842	0.5122	0.9149	0.046*
C16	1.3528 (5)	0.23453 (7)	0.59615 (19)	0.0233 (5)
C17	1.3961 (5)	0.21501 (8)	0.5141 (2)	0.0287 (6)
H17	1.2690	0.2239	0.4346	0.034*
C18	1.6227 (5)	0.18283 (8)	0.5479 (2)	0.0346 (6)
H18	1.6492	0.1694	0.4913	0.042*
C19	1.8114 (5)	0.16999 (8)	0.6633 (2)	0.0349 (6)
H19	1.9683	0.1480	0.6863	0.042*
C20	1.7708 (5)	0.18927 (8)	0.7450 (2)	0.0334 (6)
H20	1.9007	0.1805	0.8244	0.040*
C21	1.5450 (5)	0.22091 (8)	0.71255 (19)	0.0296 (6)
H21	1.5187	0.2337	0.7697	0.036*
C22	0.8584 (5)	0.34230 (9)	0.71298 (17)	0.0278 (5)
H22A	1.0310	0.3639	0.7447	0.033*
H22B	0.9296	0.3083	0.7276	0.033*
C23	0.7109 (5)	0.35207 (8)	0.77629 (18)	0.0284 (6)
H23A	0.5543	0.3277	0.7524	0.034*
H23B	0.8569	0.3488	0.8611	0.034*
C24	0.5798 (5)	0.40236 (8)	0.74956 (17)	0.0255 (5)
H24A	0.7387	0.4267	0.7786	0.031*
H24B	0.4819	0.4076	0.7907	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0244 (9)	0.0315 (9)	0.0193 (8)	0.0037 (7)	0.0062 (7)	0.0010 (7)
C1	0.0206 (12)	0.0252 (12)	0.0255 (12)	0.0021 (10)	0.0100 (10)	0.0048 (10)
C2	0.0177 (12)	0.0262 (13)	0.0251 (12)	0.0036 (10)	0.0075 (10)	0.0033 (10)
C3	0.0238 (13)	0.0232 (12)	0.0217 (11)	0.0001 (10)	0.0096 (10)	0.0011 (10)
C4	0.0194 (12)	0.0209 (12)	0.0218 (11)	−0.0016 (10)	0.0102 (10)	0.0006 (9)
C5	0.0181 (12)	0.0195 (11)	0.0234 (12)	−0.0030 (10)	0.0099 (10)	0.0007 (9)
C6	0.0171 (11)	0.0206 (11)	0.0224 (11)	0.0001 (10)	0.0096 (10)	0.0037 (10)
C7	0.0210 (12)	0.0244 (12)	0.0219 (12)	0.0009 (10)	0.0088 (10)	0.0005 (10)
C8	0.0269 (13)	0.0280 (13)	0.0209 (12)	−0.0022 (11)	0.0128 (11)	0.0000 (10)
C9	0.0289 (14)	0.0266 (13)	0.0231 (12)	−0.0027 (11)	0.0150 (11)	0.0004 (10)
C10	0.0232 (13)	0.0238 (12)	0.0271 (12)	−0.0023 (10)	0.0145 (11)	0.0001 (10)
C11	0.0214 (13)	0.0322 (14)	0.0284 (12)	−0.0025 (11)	0.0112 (11)	−0.0039 (11)
C12	0.0272 (14)	0.0322 (14)	0.0474 (16)	−0.0024 (11)	0.0219 (13)	−0.0068 (12)
C13	0.0507 (18)	0.0389 (16)	0.0488 (17)	−0.0095 (14)	0.0377 (15)	−0.0128 (13)
C14	0.0494 (19)	0.0605 (19)	0.0235 (13)	−0.0034 (15)	0.0162 (13)	−0.0085 (13)
C15	0.0321 (15)	0.0457 (16)	0.0291 (14)	0.0074 (13)	0.0115 (12)	0.0024 (12)
C16	0.0231 (13)	0.0202 (12)	0.0270 (12)	−0.0003 (10)	0.0144 (11)	−0.0002 (10)
C17	0.0299 (14)	0.0298 (13)	0.0272 (13)	−0.0013 (11)	0.0164 (11)	−0.0022 (11)
C18	0.0398 (16)	0.0328 (14)	0.0409 (15)	−0.0021 (12)	0.0285 (13)	−0.0080 (12)
C19	0.0284 (14)	0.0247 (13)	0.0535 (17)	0.0047 (11)	0.0241 (13)	0.0001 (12)
C20	0.0346 (15)	0.0272 (13)	0.0317 (13)	0.0056 (11)	0.0144 (12)	0.0045 (11)
C21	0.0395 (15)	0.0239 (12)	0.0271 (13)	0.0015 (11)	0.0197 (12)	0.0000 (10)
C22	0.0219 (12)	0.0377 (14)	0.0193 (11)	0.0063 (11)	0.0088 (10)	0.0052 (10)
C23	0.0259 (13)	0.0347 (14)	0.0206 (12)	0.0023 (11)	0.0107 (10)	0.0026 (10)
C24	0.0226 (13)	0.0298 (13)	0.0198 (11)	−0.0033 (10)	0.0093 (10)	−0.0026 (10)

Geometric parameters (Å, º)

O1—C5	1.228 (2)	C14—H14	0.9500
C1—C2	1.195 (3)	C14—C15	1.383 (3)
C1—C10	1.432 (3)	C15—H15	0.9500
C2—C3	1.417 (3)	C16—C17	1.396 (3)
C3—H3	0.9500	C16—C21	1.398 (3)
C3—C4	1.334 (3)	C17—H17	0.9500
C4—C5	1.489 (3)	C17—C18	1.379 (3)
C4—C24	1.510 (3)	C18—H18	0.9500
C5—C6	1.479 (3)	C18—C19	1.380 (3)
C6—C7	1.336 (3)	C19—H19	0.9500
C6—C22	1.514 (3)	C19—C20	1.379 (3)
C7—H7	0.9500	C20—H20	0.9500
C7—C8	1.414 (3)	C20—C21	1.370 (3)
C8—C9	1.196 (3)	C21—H21	0.9500
C9—C16	1.425 (3)	C22—H22A	0.9900
C10—C11	1.387 (3)	C22—H22B	0.9900
C10—C15	1.390 (3)	C22—C23	1.517 (3)
C11—H11	0.9500	C23—H23A	0.9900
C11—C12	1.373 (3)	C23—H23B	0.9900
C12—H12	0.9500	C23—C24	1.508 (3)
C12—C13	1.372 (3)	C24—H24A	0.9900
C13—H13	0.9500	C24—H24B	0.9900
C13—C14	1.374 (4)
C2—C1—C10	179.0 (3)	C17—C16—C9	121.1 (2)
C1—C2—C3	177.7 (2)	C17—C16—C21	118.5 (2)
C2—C3—H3	117.1	C21—C16—C9	120.5 (2)
C4—C3—C2	125.8 (2)	C16—C17—H17	119.9
C4—C3—H3	117.1	C18—C17—C16	120.3 (2)
C3—C4—C5	117.1 (2)	C18—C17—H17	119.9
C3—C4—C24	123.6 (2)	C17—C18—H18	119.7
C5—C4—C24	119.21 (19)	C17—C18—C19	120.5 (2)
O1—C5—C4	120.6 (2)	C19—C18—H18	119.7
O1—C5—C6	120.7 (2)	C18—C19—H19	120.2
C6—C5—C4	118.68 (19)	C20—C19—C18	119.6 (2)
C5—C6—C22	119.67 (19)	C20—C19—H19	120.2
C7—C6—C5	118.09 (19)	C19—C20—H20	119.7
C7—C6—C22	122.2 (2)	C21—C20—C19	120.6 (2)
C6—C7—H7	117.6	C21—C20—H20	119.7
C6—C7—C8	124.9 (2)	C16—C21—H21	119.7
C8—C7—H7	117.6	C20—C21—C16	120.6 (2)
C9—C8—C7	178.5 (2)	C20—C21—H21	119.7
C8—C9—C16	178.5 (2)	C6—C22—H22A	109.1
C11—C10—C1	120.9 (2)	C6—C22—H22B	109.1
C11—C10—C15	118.7 (2)	C6—C22—C23	112.64 (19)
C15—C10—C1	120.4 (2)	H22A—C22—H22B	107.8
C10—C11—H11	119.6	C23—C22—H22A	109.1
C12—C11—C10	120.8 (2)	C23—C22—H22B	109.1
C12—C11—H11	119.6	C22—C23—H23A	109.5
C11—C12—H12	120.0	C22—C23—H23B	109.5
C13—C12—C11	120.1 (2)	H23A—C23—H23B	108.0
C13—C12—H12	120.0	C24—C23—C22	110.91 (19)
C12—C13—H13	120.0	C24—C23—H23A	109.5
C12—C13—C14	120.1 (2)	C24—C23—H23B	109.5
C14—C13—H13	120.0	C4—C24—H24A	109.3
C13—C14—H14	119.9	C4—C24—H24B	109.3
C13—C14—C15	120.2 (2)	C23—C24—C4	111.74 (18)
C15—C14—H14	119.9	C23—C24—H24A	109.3
C10—C15—H15	120.0	C23—C24—H24B	109.3
C14—C15—C10	120.1 (2)	H24A—C24—H24B	107.9
C14—C15—H15	120.0

2,6-Bis[3-(4-bromophenyl)prop-2-yn-1-ylidene]cyclohexanone (3d)

Crystal data

C24H16Br2O	Dx = 1.589 Mg m^−3
Mr = 480.19	Synchrotron radiation, λ = 0.9699 Å
Orthorhombic, Pca21	Cell parameters from 3568 reflections
a = 12.006 (2) Å	θ = 5.3–38.6°
b = 5.2243 (10) Å	µ = 1.02 mm^−1
c = 31.998 (6) Å	T = 100 K
V = 2007.0 (7) Å^3	Needle, yellow
Z = 4	0.15 × 0.01 × 0.01 mm
F(000) = 952

Data collection

Mar CCD diffractometer	2569 reflections with I > 2σ(I)
phi–scan	Rint = 0.129
Absorption correction: multi-scan (SCALA; Evans, 2006)	θmax = 38.4°, θmin = 4.6°
	h = −14→15
9749 measured reflections	k = −6→6
3927 independent reflections	l = −38→39

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.079	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.258	(Δ/σ)max = 0.012
S = 1.00	Δρmax = 0.95 e Å^−3
3927 reflections	Δρmin = −1.42 e Å^−3
244 parameters	Absolute structure: Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.47 (7)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.94120 (15)	1.6770 (3)	0.72569 (5)	0.0503 (5)
Br2	0.90419 (16)	−1.1722 (3)	0.27438 (6)	0.0516 (6)
O1	0.5159 (11)	0.169 (2)	0.5168 (4)	0.069 (4)
C14	0.9401 (12)	1.303 (3)	0.6603 (6)	0.046 (4)
H14	1.0171	1.3416	0.6581	0.056*
C15	0.8918 (13)	1.123 (3)	0.6339 (5)	0.046 (3)
H15	0.9357	1.0400	0.6133	0.055*
C7	0.6106 (14)	−0.054 (3)	0.4458 (5)	0.055 (4)
H7	0.5319	−0.0431	0.4485	0.066*
C17	0.6827 (14)	−0.661 (3)	0.3295 (5)	0.050 (4)
H17	0.6068	−0.6144	0.3259	0.060*
C1	0.7256 (14)	0.880 (3)	0.6105 (5)	0.051 (4)
C2	0.6796 (13)	0.726 (3)	0.5886 (5)	0.050 (4)
C8	0.6544 (14)	−0.211 (3)	0.4132 (5)	0.050 (4)
C13	0.8740 (13)	1.426 (3)	0.6902 (4)	0.044 (3)
C12	0.7614 (13)	1.372 (3)	0.6946 (5)	0.046 (4)
H12	0.7168	1.4581	0.7147	0.055*
C16	0.7460 (13)	−0.544 (3)	0.3607 (5)	0.051 (4)
C9	0.6963 (15)	−0.357 (3)	0.3885 (5)	0.051 (4)
C20	0.9045 (16)	−0.802 (3)	0.3399 (6)	0.053 (4)
H20	0.9799	−0.8532	0.3435	0.063*
C6	0.6735 (13)	0.081 (3)	0.4732 (6)	0.050 (4)
C22	0.8056 (14)	0.403 (3)	0.5298 (5)	0.051 (4)
H22A	0.8405	0.2745	0.5484	0.061*
H22B	0.8325	0.5742	0.5386	0.061*
C5	0.6153 (14)	0.208 (3)	0.5089 (6)	0.054 (4)
C21	0.8582 (15)	−0.612 (3)	0.3654 (5)	0.051 (4)
H21	0.9028	−0.5282	0.3858	0.061*
C10	0.7787 (13)	1.064 (3)	0.6377 (5)	0.046 (3)
C4	0.6823 (13)	0.392 (3)	0.5350 (5)	0.047 (3)
C3	0.6262 (15)	0.546 (3)	0.5621 (5)	0.056 (4)
H3	0.5474	0.5322	0.5633	0.067*
C19	0.8392 (13)	−0.916 (3)	0.3093 (5)	0.051 (4)
C11	0.7173 (14)	1.188 (3)	0.6690 (6)	0.057 (4)
H11	0.6413	1.1428	0.6725	0.068*
C18	0.7297 (14)	−0.847 (3)	0.3036 (6)	0.051 (4)
H18	0.6865	−0.9253	0.2822	0.062*
C23	0.8424 (15)	0.353 (3)	0.4848 (6)	0.057 (4)
H23A	0.9247	0.3561	0.4831	0.068*
H23B	0.8130	0.4893	0.4663	0.068*
C24	0.7985 (12)	0.091 (3)	0.4705 (5)	0.049 (4)
H24A	0.8220	0.0588	0.4413	0.059*
H24B	0.8307	−0.0454	0.4883	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0521 (10)	0.0486 (10)	0.0502 (10)	−0.0017 (7)	−0.0008 (9)	−0.0040 (11)
Br2	0.0530 (10)	0.0492 (10)	0.0526 (11)	0.0004 (7)	0.0008 (9)	−0.0026 (11)
O1	0.040 (7)	0.086 (9)	0.082 (9)	−0.001 (5)	0.010 (6)	−0.033 (6)
C14	0.033 (8)	0.046 (9)	0.060 (11)	0.005 (6)	−0.001 (7)	0.001 (7)
C15	0.050 (9)	0.051 (8)	0.037 (8)	0.004 (6)	0.001 (7)	−0.006 (7)
C7	0.054 (9)	0.054 (10)	0.056 (9)	0.006 (7)	−0.009 (7)	−0.011 (8)
C17	0.048 (9)	0.056 (9)	0.046 (9)	0.000 (7)	0.001 (7)	−0.007 (7)
C1	0.061 (10)	0.049 (8)	0.042 (8)	0.005 (7)	0.004 (7)	0.001 (7)
C2	0.045 (9)	0.048 (8)	0.057 (11)	0.001 (7)	0.000 (7)	−0.016 (8)
C8	0.046 (9)	0.058 (9)	0.046 (9)	−0.006 (7)	−0.003 (7)	0.004 (8)
C13	0.053 (8)	0.038 (7)	0.043 (8)	0.005 (7)	0.002 (6)	0.009 (7)
C12	0.049 (9)	0.049 (8)	0.040 (8)	0.008 (7)	0.004 (6)	−0.010 (7)
C16	0.044 (8)	0.056 (10)	0.052 (9)	0.000 (7)	0.000 (7)	−0.001 (8)
C9	0.053 (10)	0.053 (9)	0.048 (9)	−0.001 (7)	−0.001 (7)	−0.004 (7)
C20	0.056 (11)	0.050 (10)	0.052 (11)	−0.001 (7)	−0.003 (8)	0.009 (8)
C6	0.044 (8)	0.044 (8)	0.063 (10)	0.001 (7)	0.004 (7)	−0.011 (8)
C22	0.053 (9)	0.047 (8)	0.053 (9)	−0.009 (7)	0.008 (7)	−0.004 (8)
C5	0.040 (10)	0.047 (9)	0.075 (13)	0.003 (6)	−0.004 (8)	−0.012 (8)
C21	0.062 (10)	0.042 (8)	0.048 (9)	−0.003 (7)	−0.004 (8)	−0.004 (7)
C10	0.059 (9)	0.036 (7)	0.042 (8)	0.003 (7)	0.007 (7)	0.000 (7)
C4	0.043 (8)	0.046 (8)	0.050 (9)	0.004 (6)	0.008 (6)	−0.005 (7)
C3	0.050 (9)	0.055 (9)	0.063 (10)	−0.004 (7)	0.006 (8)	−0.016 (8)
C19	0.052 (9)	0.053 (8)	0.048 (9)	−0.012 (7)	−0.004 (7)	−0.004 (8)
C11	0.043 (9)	0.061 (10)	0.066 (11)	−0.005 (7)	0.013 (8)	−0.014 (8)
C18	0.044 (9)	0.051 (9)	0.059 (10)	−0.004 (6)	−0.011 (8)	0.007 (8)
C23	0.048 (9)	0.066 (10)	0.056 (10)	−0.002 (7)	0.004 (8)	−0.009 (8)
C24	0.046 (8)	0.045 (8)	0.057 (10)	−0.004 (7)	−0.008 (7)	−0.012 (8)

Geometric parameters (Å, º)

Br1—C13	1.913 (16)	C20—H20	0.9500
Br2—C19	1.912 (16)	C20—C21	1.40 (2)
O1—C5	1.24 (2)	C20—C19	1.39 (2)
C14—H14	0.9500	C6—C5	1.49 (2)
C14—C15	1.39 (2)	C6—C24	1.50 (2)
C14—C13	1.40 (2)	C22—H22A	0.9900
C15—H15	0.9500	C22—H22B	0.9900
C15—C10	1.40 (2)	C22—C4	1.49 (2)
C7—H7	0.9500	C22—C23	1.53 (2)
C7—C8	1.43 (2)	C5—C4	1.51 (2)
C7—C6	1.36 (2)	C21—H21	0.9500
C17—H17	0.9500	C10—C11	1.40 (2)
C17—C16	1.40 (2)	C4—C3	1.36 (2)
C17—C18	1.40 (2)	C3—H3	0.9500
C1—C2	1.20 (2)	C19—C18	1.37 (2)
C1—C10	1.45 (2)	C11—H11	0.9500
C2—C3	1.42 (2)	C18—H18	0.9500
C8—C9	1.21 (2)	C23—H23A	0.9900
C13—C12	1.39 (2)	C23—H23B	0.9900
C12—H12	0.9500	C23—C24	1.54 (2)
C12—C11	1.37 (2)	C24—H24A	0.9900
C16—C9	1.45 (2)	C24—H24B	0.9900
C16—C21	1.40 (2)
C15—C14—H14	120.3	O1—C5—C6	122.3 (15)
C15—C14—C13	119.3 (14)	O1—C5—C4	120.5 (15)
C13—C14—H14	120.3	C6—C5—C4	117.2 (14)
C14—C15—H15	119.9	C16—C21—C20	119.8 (16)
C14—C15—C10	120.1 (14)	C16—C21—H21	120.1
C10—C15—H15	119.9	C20—C21—H21	120.1
C8—C7—H7	117.7	C15—C10—C1	121.6 (13)
C6—C7—H7	117.7	C15—C10—C11	118.1 (14)
C6—C7—C8	124.6 (15)	C11—C10—C1	120.3 (14)
C16—C17—H17	119.7	C22—C4—C5	119.6 (14)
C16—C17—C18	120.6 (16)	C3—C4—C22	122.7 (15)
C18—C17—H17	119.7	C3—C4—C5	117.8 (14)
C2—C1—C10	178.6 (18)	C2—C3—H3	118.4
C1—C2—C3	179.0 (19)	C4—C3—C2	123.3 (16)
C9—C8—C7	173.8 (17)	C4—C3—H3	118.4
C14—C13—Br1	118.9 (11)	C20—C19—Br2	118.8 (13)
C12—C13—Br1	119.4 (11)	C18—C19—Br2	119.7 (12)
C12—C13—C14	121.8 (14)	C18—C19—C20	121.6 (15)
C13—C12—H12	121.3	C12—C11—C10	123.2 (15)
C11—C12—C13	117.4 (14)	C12—C11—H11	118.4
C11—C12—H12	121.3	C10—C11—H11	118.4
C17—C16—C9	120.7 (15)	C17—C18—H18	120.4
C17—C16—C21	119.4 (15)	C19—C18—C17	119.3 (16)
C21—C16—C9	119.9 (15)	C19—C18—H18	120.4
C8—C9—C16	176.8 (17)	C22—C23—H23A	109.8
C21—C20—H20	120.3	C22—C23—H23B	109.8
C19—C20—H20	120.3	C22—C23—C24	109.5 (14)
C19—C20—C21	119.3 (16)	H23A—C23—H23B	108.2
C7—C6—C5	117.7 (14)	C24—C23—H23A	109.8
C7—C6—C24	122.3 (14)	C24—C23—H23B	109.8
C5—C6—C24	119.8 (14)	C6—C24—C23	110.7 (14)
H22A—C22—H22B	107.8	C6—C24—H24A	109.5
C4—C22—H22A	109.1	C6—C24—H24B	109.5
C4—C22—H22B	109.1	C23—C24—H24A	109.5
C4—C22—C23	112.6 (14)	C23—C24—H24B	109.5
C23—C22—H22A	109.1	H24A—C24—H24B	108.1
C23—C22—H22B	109.1

4-tert-Butyl-2,6-bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone (3e)

Crystal data

C28H25O	F(000) = 804
Mr = 377.48	Dx = 1.136 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.9422 (14) Å	Cell parameters from 3825 reflections
b = 6.9614 (7) Å	θ = 2.8–30.5°
c = 24.721 (3) Å	µ = 0.07 mm^−1
β = 97.732 (2)°	T = 120 K
V = 2207.0 (4) Å^3	Needle, yellow
Z = 4	0.48 × 0.01 × 0.01 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer	6739 independent reflections
Radiation source: sealed tube	2902 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.165
Detector resolution: 8 pixels mm^-1	θmax = 30.6°, θmin = 1.7°
ω and φ scans	h = −18→18
Absorption correction: multi-scan SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1821 before and 0.0591 after correction. The Ratio of minimum to maximum transmission is 0.5936. The λ/2 correction factor is 0.00150.	k = −9→9
Tmin = 0.443, Tmax = 0.746	l = −35→35
36697 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.078	H-atom parameters constrained
wR(F^2) = 0.163	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
6739 reflections	Δρmax = 0.41 e Å^−3
304 parameters	Δρmin = −0.17 e Å^−3
36 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.37750 (10)	0.2693 (2)	0.47019 (5)	0.0430 (4)
C1	0.55701 (14)	0.2194 (3)	0.67830 (8)	0.0338 (4)
C2	0.52205 (14)	0.2311 (3)	0.63087 (8)	0.0367 (5)
C3	0.47789 (15)	0.2434 (3)	0.57535 (7)	0.0389 (5)
H3	0.4041	0.2525	0.5676	0.047*
C4	0.53249 (14)	0.2433 (3)	0.53268 (7)	0.0333 (4)
C5	0.47354 (14)	0.2606 (3)	0.47740 (7)	0.0336 (4)
C6	0.53363 (14)	0.2657 (3)	0.43039 (7)	0.0415 (5)
C7	0.48361 (14)	0.2570 (3)	0.38011 (7)	0.0331 (4)
H7	0.4096	0.2511	0.3761	0.040*
C8	0.53114 (14)	0.2557 (3)	0.33169 (7)	0.0335 (4)
C9	0.57153 (14)	0.2512 (2)	0.29079 (7)	0.0323 (4)
C10	0.59790 (14)	0.2086 (2)	0.73488 (7)	0.0313 (4)
C11	0.55096 (15)	0.3125 (3)	0.77338 (8)	0.0384 (5)
H11	0.4908	0.3879	0.7619	0.046*
C12	0.59114 (16)	0.3064 (3)	0.82770 (8)	0.0438 (5)
H12	0.5589	0.3781	0.8535	0.053*
C13	0.67802 (16)	0.1966 (3)	0.84486 (8)	0.0440 (5)
H13	0.7063	0.1941	0.8824	0.053*
C14	0.72383 (15)	0.0905 (3)	0.80746 (8)	0.0455 (5)
H14	0.7827	0.0124	0.8195	0.055*
C15	0.68492 (14)	0.0967 (3)	0.75281 (8)	0.0390 (5)
H15	0.7176	0.0244	0.7273	0.047*
C16	0.64889 (14)	0.2301 (3)	0.54116 (8)	0.0479 (5)
H16A	0.6765	0.3435	0.5625	0.057*
H16B	0.6689	0.1150	0.5636	0.057*
C17	0.70079 (15)	0.2195 (4)	0.49164 (8)	0.0528 (6)
C19	0.61877 (14)	0.2410 (2)	0.24173 (7)	0.0307 (4)
C20	0.56410 (15)	0.1614 (3)	0.19490 (8)	0.0438 (5)
H20	0.4946	0.1178	0.1951	0.053*
C21	0.61104 (18)	0.1457 (3)	0.14801 (8)	0.0574 (6)
H21	0.5739	0.0893	0.1162	0.069*
C22	0.71109 (18)	0.2112 (3)	0.14710 (9)	0.0540 (6)
H22	0.7425	0.2014	0.1146	0.065*
C23	0.76561 (16)	0.2908 (3)	0.19325 (9)	0.0480 (5)
H23	0.8347	0.3360	0.1925	0.058*
C24	0.72047 (15)	0.3053 (3)	0.24064 (8)	0.0390 (5)
H24	0.7588	0.3591	0.2725	0.047*
C25	0.82077 (14)	0.2134 (3)	0.50075 (8)	0.0430 (5)
C18	0.6479 (2)	0.3162 (6)	0.44357 (11)	0.0436 (7)	0.7
H18A	0.6836	0.2830	0.4118	0.052*	0.7
H18B	0.6543	0.4567	0.4492	0.052*	0.7
C26	0.8553 (3)	0.4235 (6)	0.50859 (15)	0.0593 (11)	0.6
H26A	0.8313	0.4964	0.4753	0.089*	0.6
H26B	0.9315	0.4295	0.5161	0.089*	0.6
H26C	0.8251	0.4789	0.5394	0.089*	0.6
C27	0.8630 (3)	0.1323 (8)	0.44951 (16)	0.0693 (12)	0.6
H27A	0.8392	−0.0005	0.4433	0.104*	0.6
H27B	0.9394	0.1353	0.4553	0.104*	0.6
H27C	0.8371	0.2108	0.4176	0.104*	0.6
C28	0.8626 (3)	0.0952 (7)	0.55006 (16)	0.0625 (11)	0.6
H28A	0.8408	0.1529	0.5829	0.094*	0.6
H28B	0.9389	0.0919	0.5537	0.094*	0.6
H28C	0.8352	−0.0359	0.5457	0.094*	0.6
C18A	0.6494 (4)	0.1728 (10)	0.4419 (2)	0.0265 (13)	0.3
H18C	0.6436	0.0312	0.4392	0.032*	0.3
H18D	0.6907	0.2173	0.4134	0.032*	0.3
C26A	0.8747 (5)	0.2903 (12)	0.5563 (3)	0.079 (2)	0.4
H26D	0.8661	0.4300	0.5576	0.118*	0.4
H26E	0.9492	0.2589	0.5603	0.118*	0.4
H26F	0.8431	0.2307	0.5860	0.118*	0.4
C27A	0.8751 (5)	0.3016 (11)	0.4568 (3)	0.0715 (19)	0.4
H27D	0.8464	0.2477	0.4213	0.107*	0.4
H27E	0.9499	0.2738	0.4641	0.107*	0.4
H27F	0.8643	0.4410	0.4564	0.107*	0.4
C28A	0.8410 (4)	−0.0044 (8)	0.5024 (3)	0.0574 (15)	0.4
H28D	0.7999	−0.0647	0.5282	0.086*	0.4
H28E	0.9153	−0.0285	0.5140	0.086*	0.4
H28F	0.8208	−0.0587	0.4659	0.086*	0.4

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0313 (7)	0.0606 (9)	0.0387 (8)	0.0078 (7)	0.0106 (6)	0.0009 (6)
C1	0.0375 (10)	0.0309 (10)	0.0363 (12)	−0.0036 (8)	0.0175 (9)	−0.0015 (8)
C2	0.0390 (11)	0.0410 (12)	0.0333 (11)	−0.0039 (9)	0.0169 (9)	−0.0004 (9)
C3	0.0368 (10)	0.0483 (12)	0.0339 (11)	0.0001 (10)	0.0128 (8)	0.0012 (9)
C4	0.0351 (10)	0.0367 (11)	0.0298 (10)	−0.0002 (9)	0.0105 (8)	0.0003 (8)
C5	0.0328 (10)	0.0371 (11)	0.0324 (10)	0.0048 (9)	0.0105 (8)	0.0018 (8)
C6	0.0318 (10)	0.0633 (14)	0.0310 (11)	0.0050 (10)	0.0104 (8)	0.0051 (9)
C7	0.0325 (10)	0.0338 (11)	0.0332 (10)	0.0071 (8)	0.0058 (8)	0.0024 (8)
C8	0.0359 (10)	0.0330 (11)	0.0307 (10)	0.0061 (9)	0.0015 (8)	0.0024 (8)
C9	0.0362 (10)	0.0276 (10)	0.0326 (10)	0.0031 (8)	0.0030 (8)	0.0030 (8)
C10	0.0350 (10)	0.0284 (10)	0.0322 (10)	−0.0047 (8)	0.0111 (8)	−0.0019 (8)
C11	0.0417 (11)	0.0366 (11)	0.0379 (11)	0.0064 (9)	0.0094 (9)	−0.0001 (9)
C12	0.0525 (13)	0.0466 (13)	0.0346 (11)	0.0046 (10)	0.0143 (10)	−0.0074 (9)
C13	0.0482 (12)	0.0477 (13)	0.0351 (11)	−0.0008 (11)	0.0020 (9)	−0.0023 (9)
C14	0.0405 (12)	0.0426 (12)	0.0519 (14)	0.0065 (10)	0.0004 (10)	−0.0048 (10)
C15	0.0381 (11)	0.0405 (12)	0.0402 (12)	0.0016 (9)	0.0119 (9)	−0.0102 (9)
C16	0.0331 (11)	0.0770 (16)	0.0345 (11)	−0.0006 (11)	0.0081 (8)	0.0043 (10)
C17	0.0287 (10)	0.1027 (19)	0.0285 (11)	0.0149 (11)	0.0098 (8)	0.0147 (11)
C19	0.0351 (10)	0.0275 (10)	0.0305 (10)	0.0041 (8)	0.0082 (8)	0.0030 (8)
C20	0.0388 (11)	0.0545 (13)	0.0385 (12)	−0.0057 (10)	0.0063 (9)	−0.0026 (9)
C21	0.0602 (15)	0.0797 (18)	0.0334 (12)	−0.0090 (13)	0.0102 (10)	−0.0126 (11)
C22	0.0618 (15)	0.0611 (15)	0.0439 (13)	−0.0021 (12)	0.0250 (11)	−0.0062 (11)
C23	0.0452 (12)	0.0433 (13)	0.0597 (14)	−0.0051 (10)	0.0229 (11)	0.0006 (10)
C24	0.0422 (12)	0.0336 (11)	0.0414 (12)	−0.0029 (9)	0.0069 (9)	−0.0044 (8)
C25	0.0300 (10)	0.0619 (14)	0.0385 (11)	0.0029 (10)	0.0093 (8)	0.0091 (10)
C18	0.0341 (17)	0.063 (2)	0.0356 (17)	0.0014 (17)	0.0129 (13)	0.0104 (16)
C26	0.0322 (19)	0.089 (3)	0.057 (2)	−0.0208 (19)	0.0070 (17)	0.016 (2)
C27	0.042 (2)	0.103 (3)	0.068 (3)	0.025 (2)	0.0232 (19)	0.004 (3)
C28	0.035 (2)	0.090 (3)	0.062 (3)	0.017 (2)	0.0027 (18)	0.031 (2)
C18A	0.019 (3)	0.027 (3)	0.035 (4)	0.002 (3)	0.013 (3)	−0.009 (3)
C26A	0.049 (3)	0.105 (5)	0.080 (4)	−0.008 (4)	0.000 (3)	−0.025 (4)
C27A	0.041 (3)	0.084 (4)	0.093 (4)	−0.004 (3)	0.021 (3)	0.023 (4)
C28A	0.033 (3)	0.062 (4)	0.077 (4)	0.009 (3)	0.012 (3)	0.004 (3)

Geometric parameters (Å, º)

O1—C5	1.233 (2)	C20—C21	1.384 (3)
C1—C2	1.201 (2)	C21—H21	0.9500
C1—C10	1.430 (3)	C21—C22	1.376 (3)
C2—C3	1.416 (3)	C22—H22	0.9500
C3—H3	0.9500	C22—C23	1.375 (3)
C3—C4	1.346 (2)	C23—H23	0.9500
C4—C5	1.478 (2)	C23—C24	1.381 (3)
C4—C16	1.496 (2)	C24—H24	0.9500
C5—C6	1.483 (2)	C25—C26	1.534 (4)
C6—C7	1.323 (2)	C25—C27	1.552 (4)
C6—C18	1.513 (3)	C25—C28	1.509 (4)
C6—C18A	1.622 (6)	C25—C26A	1.549 (6)
C7—H7	0.9500	C25—C27A	1.502 (6)
C7—C8	1.417 (2)	C25—C28A	1.538 (6)
C8—C9	1.200 (2)	C18—H18A	0.9900
C9—C19	1.431 (2)	C18—H18B	0.9900
C10—C11	1.398 (2)	C26—H26A	0.9800
C10—C15	1.392 (3)	C26—H26B	0.9800
C11—H11	0.9500	C26—H26C	0.9800
C11—C12	1.374 (3)	C27—H27A	0.9800
C12—H12	0.9500	C27—H27B	0.9800
C12—C13	1.378 (3)	C27—H27C	0.9800
C13—H13	0.9500	C28—H28A	0.9800
C13—C14	1.378 (3)	C28—H28B	0.9800
C14—H14	0.9500	C28—H28C	0.9800
C14—C15	1.378 (3)	C18A—H18C	0.9900
C15—H15	0.9500	C18A—H18D	0.9900
C16—H16A	0.9900	C26A—H26D	0.9800
C16—H16B	0.9900	C26A—H26E	0.9800
C16—C17	1.475 (2)	C26A—H26F	0.9800
C17—C25	1.539 (3)	C27A—H27D	0.9800
C17—C18	1.455 (3)	C27A—H27E	0.9800
C17—C18A	1.355 (6)	C27A—H27F	0.9800
C19—C20	1.388 (3)	C28A—H28D	0.9800
C19—C24	1.394 (3)	C28A—H28E	0.9800
C20—H20	0.9500	C28A—H28F	0.9800
C2—C1—C10	179.1 (2)	C24—C23—H23	119.8
C1—C2—C3	178.31 (19)	C19—C24—H24	120.0
C2—C3—H3	117.5	C23—C24—C19	120.07 (18)
C4—C3—C2	124.98 (17)	C23—C24—H24	120.0
C4—C3—H3	117.5	C17—C25—C27	110.5 (2)
C3—C4—C5	117.67 (16)	C17—C25—C26A	116.5 (3)
C3—C4—C16	121.00 (16)	C26—C25—C17	105.3 (2)
C5—C4—C16	121.31 (15)	C26—C25—C27	108.7 (3)
O1—C5—C4	121.52 (15)	C28—C25—C17	112.2 (2)
O1—C5—C6	120.67 (16)	C28—C25—C26	110.6 (3)
C4—C5—C6	117.81 (15)	C28—C25—C27	109.5 (3)
C5—C6—C18	115.94 (18)	C27A—C25—C17	116.3 (3)
C5—C6—C18A	115.0 (2)	C27A—C25—C26A	107.5 (4)
C7—C6—C5	119.54 (17)	C27A—C25—C28A	109.1 (4)
C7—C6—C18	123.61 (18)	C28A—C25—C17	101.3 (3)
C7—C6—C18A	118.1 (2)	C28A—C25—C26A	105.2 (4)
C6—C7—H7	117.3	C6—C18—H18A	108.7
C6—C7—C8	125.48 (17)	C6—C18—H18B	108.7
C8—C7—H7	117.3	C17—C18—C6	114.0 (2)
C9—C8—C7	178.87 (19)	C17—C18—H18A	108.7
C8—C9—C19	178.5 (2)	C17—C18—H18B	108.7
C11—C10—C1	120.08 (17)	H18A—C18—H18B	107.6
C15—C10—C1	121.23 (16)	C25—C26—H26A	109.5
C15—C10—C11	118.69 (16)	C25—C26—H26B	109.5
C10—C11—H11	119.7	C25—C26—H26C	109.5
C12—C11—C10	120.50 (18)	H26A—C26—H26B	109.5
C12—C11—H11	119.7	H26A—C26—H26C	109.5
C11—C12—H12	119.9	H26B—C26—H26C	109.5
C11—C12—C13	120.23 (18)	C25—C27—H27A	109.5
C13—C12—H12	119.9	C25—C27—H27B	109.5
C12—C13—H13	120.1	C25—C27—H27C	109.5
C14—C13—C12	119.85 (19)	H27A—C27—H27B	109.5
C14—C13—H13	120.1	H27A—C27—H27C	109.5
C13—C14—H14	119.8	H27B—C27—H27C	109.5
C15—C14—C13	120.49 (19)	C25—C28—H28A	109.5
C15—C14—H14	119.8	C25—C28—H28B	109.5
C10—C15—H15	119.9	C25—C28—H28C	109.5
C14—C15—C10	120.22 (17)	H28A—C28—H28B	109.5
C14—C15—H15	119.9	H28A—C28—H28C	109.5
C4—C16—H16A	108.1	H28B—C28—H28C	109.5
C4—C16—H16B	108.1	C6—C18A—H18C	109.0
H16A—C16—H16B	107.3	C6—C18A—H18D	109.0
C17—C16—C4	116.69 (16)	C17—C18A—C6	113.1 (4)
C17—C16—H16A	108.1	C17—C18A—H18C	109.0
C17—C16—H16B	108.1	C17—C18A—H18D	109.0
C16—C17—C25	116.29 (16)	H18C—C18A—H18D	107.8
C18—C17—C16	115.98 (19)	C25—C26A—H26D	109.5
C18—C17—C25	119.12 (18)	C25—C26A—H26E	109.5
C18A—C17—C16	122.8 (3)	C25—C26A—H26F	109.5
C18A—C17—C25	119.2 (3)	H26D—C26A—H26E	109.5
C20—C19—C9	119.90 (17)	H26D—C26A—H26F	109.5
C20—C19—C24	119.25 (16)	H26E—C26A—H26F	109.5
C24—C19—C9	120.82 (16)	C25—C27A—H27D	109.5
C19—C20—H20	120.1	C25—C27A—H27E	109.5
C21—C20—C19	119.88 (19)	C25—C27A—H27F	109.5
C21—C20—H20	120.1	H27D—C27A—H27E	109.5
C20—C21—H21	119.7	H27D—C27A—H27F	109.5
C22—C21—C20	120.5 (2)	H27E—C27A—H27F	109.5
C22—C21—H21	119.7	C25—C28A—H28D	109.5
C21—C22—H22	120.0	C25—C28A—H28E	109.5
C23—C22—C21	119.93 (19)	C25—C28A—H28F	109.5
C23—C22—H22	120.0	H28D—C28A—H28E	109.5
C22—C23—H23	119.8	H28D—C28A—H28F	109.5
C22—C23—C24	120.33 (19)	H28E—C28A—H28F	109.5
O1—C5—C6—C7	−7.9 (3)	C16—C17—C25—C27	160.2 (3)
O1—C5—C6—C18	161.6 (2)	C16—C17—C25—C28	37.7 (3)
O1—C5—C6—C18A	−157.3 (3)	C16—C17—C25—C26A	−21.1 (5)
C1—C10—C11—C12	−178.50 (17)	C16—C17—C25—C27A	−149.5 (4)
C1—C10—C15—C14	179.11 (18)	C16—C17—C25—C28A	92.4 (3)
C2—C3—C4—C5	−178.96 (17)	C16—C17—C18—C6	−49.9 (4)
C2—C3—C4—C16	−0.2 (3)	C16—C17—C18A—C6	39.1 (6)
C3—C4—C5—O1	−2.1 (3)	C19—C20—C21—C22	−1.0 (3)
C3—C4—C5—C6	178.41 (18)	C20—C19—C24—C23	0.5 (3)
C3—C4—C16—C17	176.5 (2)	C20—C21—C22—C23	0.8 (4)
C4—C5—C6—C7	171.65 (17)	C21—C22—C23—C24	0.1 (3)
C4—C5—C6—C18	−18.9 (3)	C22—C23—C24—C19	−0.7 (3)
C4—C5—C6—C18A	22.2 (3)	C24—C19—C20—C21	0.4 (3)
C4—C16—C17—C25	177.85 (19)	C25—C17—C18—C6	163.5 (2)
C4—C16—C17—C18	30.2 (3)	C25—C17—C18A—C6	−156.3 (3)
C4—C16—C17—C18A	−17.1 (5)	C18—C6—C7—C8	13.0 (3)
C5—C4—C16—C17	−4.8 (3)	C18—C6—C18A—C17	59.2 (4)
C5—C6—C7—C8	−178.37 (17)	C18—C17—C25—C26	64.0 (3)
C5—C6—C18—C17	44.0 (3)	C18—C17—C25—C27	−53.2 (4)
C5—C6—C18A—C17	−41.4 (5)	C18—C17—C25—C28	−175.7 (3)
C7—C6—C18—C17	−147.0 (2)	C18—C17—C25—C26A	125.4 (4)
C7—C6—C18A—C17	168.7 (3)	C18—C17—C25—C27A	−3.0 (5)
C9—C19—C20—C21	−177.85 (19)	C18—C17—C25—C28A	−121.1 (3)
C9—C19—C24—C23	178.68 (17)	C18—C17—C18A—C6	−54.2 (4)
C10—C11—C12—C13	−0.4 (3)	C18A—C6—C7—C8	−29.9 (4)
C11—C10—C15—C14	−0.4 (3)	C18A—C6—C18—C17	−53.7 (4)
C11—C12—C13—C14	−0.9 (3)	C18A—C17—C25—C26	111.9 (4)
C12—C13—C14—C15	1.5 (3)	C18A—C17—C25—C27	−5.4 (5)
C13—C14—C15—C10	−0.9 (3)	C18A—C17—C25—C28	−127.8 (4)
C15—C10—C11—C12	1.0 (3)	C18A—C17—C25—C26A	173.3 (5)
C16—C4—C5—O1	179.17 (18)	C18A—C17—C25—C27A	44.9 (6)
C16—C4—C5—C6	−0.3 (3)	C18A—C17—C25—C28A	−73.2 (5)
C16—C17—C25—C26	−82.6 (3)	C18A—C17—C18—C6	61.1 (4)

4-tert-Butyl-2,6-bis[3-(4-methylphenyl)prop-2-yn-1-ylidene]cyclohexanone (3f)

Crystal data

C30H30O	F(000) = 872
Mr = 406.54	Dx = 1.090 Mg m^−3
Monoclinic, Cc	Synchrotron radiation, λ = 0.96990 Å
a = 6.4010 (13) Å	Cell parameters from 3567 reflections
b = 21.350 (4) Å	θ = 3.1–38.7°
c = 18.190 (4) Å	µ = 0.14 mm^−1
β = 94.83 (3)°	T = 120 K
V = 2477.1 (9) Å^3	Needle, yellow
Z = 4	0.5 × 0.02 × 0.02 mm

Data collection

Mar CCD diffractometer	2588 independent reflections
Radiation source: fine-focus sealed tube	1287 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.238
phi–scan	θmax = 38.4°, θmin = 2.6°
Absorption correction: multi-scan (SCALA; Evans, 2006)	h = −7→8
Tmin = 0.899, Tmax = 0.902	k = −26→25
10989 measured reflections	l = −21→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.140	H-atom parameters constrained
wR(F^2) = 0.339	w = 1/[σ^2(Fo^2) + (0.010P)^2 + 3.2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2588 reflections	Δρmax = 0.37 e Å^−3
279 parameters	Δρmin = −0.32 e Å^−3
23 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.146 (19)

Special details

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.

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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.6468 (12)	0.5022 (3)	0.3726 (4)	0.0721 (19)
C20	1.2839 (15)	0.7564 (4)	0.3294 (5)	0.057 (2)
C3	0.8961 (16)	0.6089 (5)	0.3589 (5)	0.066 (3)
H3	0.8949	0.5766	0.3229	0.079*
C1	1.1471 (16)	0.7050 (5)	0.3427 (5)	0.063 (3)
C16	−0.5004 (15)	0.4357 (4)	0.6742 (5)	0.058 (2)
C5	0.6225 (14)	0.5465 (4)	0.4149 (4)	0.058 (2)
C7	0.4256 (16)	0.6031 (4)	0.5156 (5)	0.064 (3)
H7AA	0.4790	0.5911	0.5663	0.076*	0.50
H7AB	0.2740	0.6120	0.5163	0.076*	0.50
H7BC	0.2864	0.6218	0.5016	0.076*	0.50
H7BD	0.4219	0.5866	0.5664	0.076*	0.50
C2	1.0343 (15)	0.6607 (5)	0.3528 (5)	0.059 (2)
C13	−0.1701 (14)	0.4651 (4)	0.5893 (5)	0.056 (2)
C14	−0.2113 (16)	0.5039 (4)	0.6478 (5)	0.061 (2)
H14	−0.1280	0.5401	0.6587	0.073*
C25	1.4813 (15)	0.7444 (4)	0.2978 (5)	0.059 (3)
H25	1.5184	0.7029	0.2853	0.071*
C6	0.4518 (15)	0.5487 (4)	0.4658 (4)	0.054 (2)
C18	−0.2899 (17)	0.4120 (4)	0.5732 (6)	0.070 (3)
H18	−0.2594	0.3854	0.5337	0.084*
C15	−0.3830 (16)	0.4886 (4)	0.6922 (5)	0.062 (3)
H15	−0.4135	0.5144	0.7325	0.074*
C4	0.7618 (15)	0.6034 (4)	0.4157 (5)	0.059 (2)
C12	0.0043 (17)	0.4797 (4)	0.5464 (6)	0.066 (3)
C10	0.3228 (17)	0.4973 (5)	0.4630 (5)	0.070 (3)
H10	0.3511	0.4648	0.4295	0.084*
C17	−0.4578 (18)	0.3979 (5)	0.6160 (6)	0.069 (3)
H17	−0.5421	0.3620	0.6046	0.083*
C24	1.6161 (17)	0.7943 (4)	0.2859 (6)	0.070 (3)
H24	1.7490	0.7859	0.2684	0.084*
C11	0.1459 (18)	0.4886 (4)	0.5073 (6)	0.066 (3)
C21	1.237 (2)	0.8178 (5)	0.3458 (6)	0.075 (3)
H21	1.1089	0.8267	0.3668	0.090*
C22	1.372 (2)	0.8671 (5)	0.3321 (7)	0.088 (4)
H22	1.3374	0.9087	0.3450	0.105*
C27	0.5296 (17)	0.7143 (5)	0.5598 (6)	0.078 (3)
C19	−0.6853 (16)	0.4200 (5)	0.7179 (7)	0.076 (3)
H19A	−0.6420	0.4225	0.7708	0.114*
H19B	−0.7343	0.3775	0.7056	0.114*
H19C	−0.7990	0.4499	0.7055	0.114*
C23	1.560 (2)	0.8549 (4)	0.2990 (7)	0.086 (4)
C8	0.541 (3)	0.6655 (7)	0.4940 (12)	0.061 (4)*	0.50
H8	0.4766	0.6831	0.4464	0.073*	0.50
C26	1.708 (2)	0.9096 (5)	0.2783 (7)	0.093 (4)
H26A	1.8464	0.9043	0.3051	0.139*
H26B	1.6481	0.9498	0.2918	0.139*
H26C	1.7224	0.9089	0.2251	0.139*
C9	0.767 (3)	0.6405 (9)	0.4860 (12)	0.067 (4)*	0.50
H9A	0.8659	0.6759	0.4843	0.081*	0.50
H9B	0.8130	0.6136	0.5286	0.081*	0.50
C29	0.316 (4)	0.7380 (11)	0.5528 (15)	0.078 (4)*	0.50
H29A	0.2672	0.7415	0.5005	0.118*	0.50
H29B	0.3124	0.7793	0.5761	0.118*	0.50
H29C	0.2250	0.7091	0.5771	0.118*	0.50
C28	0.642 (6)	0.7750 (16)	0.530 (2)	0.098 (5)*	0.50
H28A	0.7925	0.7730	0.5440	0.147*	0.50
H28B	0.5829	0.8127	0.5507	0.147*	0.50
H28C	0.6181	0.7765	0.4757	0.147*	0.50
C30	0.606 (5)	0.6894 (13)	0.6385 (16)	0.099 (6)*	0.50
H30A	0.5991	0.7233	0.6745	0.148*	0.50
H30B	0.7508	0.6746	0.6386	0.148*	0.50
H30C	0.5156	0.6548	0.6516	0.148*	0.50
C9A	0.728 (4)	0.6644 (10)	0.4619 (13)	0.067 (4)*	0.50
H9AA	0.8636	0.6783	0.4865	0.081*	0.50
H9AB	0.6732	0.6983	0.4284	0.081*	0.50
C8A	0.578 (3)	0.6530 (8)	0.5182 (11)	0.061 (4)*	0.50
H8A	0.6803	0.6347	0.5570	0.073*	0.50
C30A	0.677 (3)	0.7102 (12)	0.6269 (12)	0.099 (6)*	0.50
H30D	0.6979	0.6662	0.6409	0.148*	0.50
H30E	0.6193	0.7330	0.6673	0.148*	0.50
H30F	0.8120	0.7287	0.6169	0.148*	0.50
C29A	0.299 (2)	0.7231 (11)	0.5767 (13)	0.078 (4)*	0.50
H29D	0.2096	0.7249	0.5303	0.118*	0.50
H29E	0.2854	0.7621	0.6041	0.118*	0.50
H29F	0.2563	0.6877	0.6063	0.118*	0.50
C28A	0.589 (4)	0.7761 (13)	0.5185 (16)	0.098 (5)*	0.50
H28D	0.7254	0.7708	0.4989	0.147*	0.50
H28E	0.5949	0.8113	0.5532	0.147*	0.50
H28F	0.4819	0.7845	0.4778	0.147*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.089 (5)	0.071 (4)	0.059 (4)	0.012 (3)	0.023 (3)	−0.013 (3)
C20	0.065 (6)	0.058 (5)	0.045 (5)	0.012 (5)	−0.011 (5)	−0.011 (4)
C3	0.075 (7)	0.078 (6)	0.044 (5)	0.011 (5)	0.005 (5)	0.004 (4)
C1	0.067 (7)	0.077 (6)	0.040 (5)	0.025 (6)	−0.016 (5)	−0.002 (4)
C16	0.063 (6)	0.056 (4)	0.054 (5)	−0.002 (5)	−0.002 (4)	0.009 (4)
C5	0.064 (6)	0.072 (6)	0.039 (4)	0.008 (5)	0.008 (4)	−0.011 (4)
C7	0.081 (7)	0.057 (5)	0.052 (5)	0.002 (5)	0.002 (5)	−0.001 (4)
C2	0.059 (6)	0.070 (6)	0.046 (5)	0.018 (5)	−0.003 (4)	−0.003 (4)
C13	0.060 (6)	0.057 (4)	0.050 (5)	−0.003 (4)	−0.003 (4)	0.008 (4)
C14	0.067 (6)	0.061 (5)	0.053 (5)	−0.003 (5)	0.002 (5)	−0.001 (4)
C25	0.074 (7)	0.057 (5)	0.043 (5)	0.000 (5)	−0.018 (5)	0.000 (4)
C6	0.068 (6)	0.055 (5)	0.039 (4)	0.021 (4)	0.011 (4)	0.000 (3)
C18	0.080 (7)	0.048 (5)	0.082 (7)	−0.011 (5)	0.007 (6)	0.000 (4)
C15	0.075 (7)	0.051 (5)	0.060 (5)	−0.009 (4)	0.009 (5)	0.012 (4)
C4	0.065 (6)	0.063 (5)	0.051 (5)	0.014 (5)	0.009 (5)	−0.003 (4)
C12	0.067 (7)	0.066 (6)	0.065 (6)	0.000 (5)	0.004 (6)	0.009 (5)
C10	0.085 (8)	0.074 (6)	0.049 (5)	0.002 (6)	−0.002 (5)	−0.003 (4)
C17	0.079 (7)	0.060 (5)	0.066 (6)	−0.001 (5)	−0.006 (5)	−0.001 (5)
C24	0.065 (7)	0.057 (5)	0.085 (7)	−0.009 (5)	−0.007 (5)	0.002 (5)
C11	0.074 (7)	0.068 (6)	0.055 (6)	−0.001 (5)	−0.006 (6)	0.006 (5)
C21	0.102 (8)	0.060 (5)	0.060 (6)	0.028 (6)	−0.015 (6)	−0.006 (4)
C22	0.111 (10)	0.060 (6)	0.086 (8)	0.031 (7)	−0.033 (8)	−0.024 (5)
C27	0.072 (5)	0.092 (5)	0.072 (5)	−0.019 (4)	0.014 (4)	−0.021 (4)
C19	0.060 (6)	0.079 (6)	0.088 (7)	−0.002 (5)	0.005 (5)	0.038 (6)
C23	0.111 (10)	0.044 (5)	0.091 (8)	−0.008 (6)	−0.056 (8)	0.004 (5)
C26	0.091 (6)	0.083 (5)	0.101 (6)	−0.009 (5)	−0.012 (5)	0.005 (5)

Geometric parameters (Å, º)

O1—C5	1.238 (10)	C22—C23	1.416 (19)
C20—C1	1.439 (15)	C27—C8	1.59 (2)
C20—C25	1.454 (14)	C27—C29	1.45 (3)
C20—C21	1.383 (12)	C27—C28	1.60 (3)
C3—H3	0.9500	C27—C30	1.57 (3)
C3—C2	1.426 (16)	C27—C8A	1.56 (2)
C3—C4	1.402 (13)	C27—C30A	1.482 (16)
C1—C2	1.213 (14)	C27—C29A	1.543 (16)
C16—C15	1.380 (13)	C27—C28A	1.579 (17)
C16—C17	1.377 (14)	C19—H19A	0.9800
C16—C19	1.517 (14)	C19—H19B	0.9800
C5—C6	1.491 (12)	C19—H19C	0.9800
C5—C4	1.505 (13)	C23—C26	1.569 (17)
C7—H7AA	0.9900	C8—H8	1.0000
C7—H7AB	0.9900	C8—C9	1.559 (18)
C7—H7BC	0.9900	C26—H26A	0.9800
C7—H7BD	0.9900	C26—H26B	0.9800
C7—C6	1.491 (11)	C26—H26C	0.9800
C7—C8	1.589 (15)	C9—H9A	0.9900
C7—C8A	1.446 (15)	C9—H9B	0.9900
C13—C14	1.390 (13)	C29—H29A	0.9800
C13—C18	1.387 (12)	C29—H29B	0.9800
C13—C12	1.449 (14)	C29—H29C	0.9800
C14—H14	0.9500	C28—H28A	0.9800
C14—C15	1.454 (14)	C28—H28B	0.9800
C25—H25	0.9500	C28—H28C	0.9800
C25—C24	1.399 (13)	C30—H30A	0.9800
C6—C10	1.373 (13)	C30—H30B	0.9800
C18—H18	0.9500	C30—H30C	0.9800
C18—C17	1.412 (15)	C9A—H9AA	0.9900
C15—H15	0.9500	C9A—H9AB	0.9900
C4—C9	1.50 (2)	C9A—C8A	1.48 (3)
C4—C9A	1.58 (2)	C8A—H8A	1.0000
C12—C11	1.213 (15)	C30A—H30D	0.9800
C10—H10	0.9500	C30A—H30E	0.9800
C10—C11	1.457 (16)	C30A—H30F	0.9800
C17—H17	0.9500	C29A—H29D	0.9800
C24—H24	0.9500	C29A—H29E	0.9800
C24—C23	1.370 (14)	C29A—H29F	0.9800
C21—H21	0.9500	C28A—H28D	0.9800
C21—C22	1.398 (19)	C28A—H28E	0.9800
C22—H22	0.9500	C28A—H28F	0.9800
C1—C20—C25	119.5 (7)	C30—C27—C28	118.3 (19)
C21—C20—C1	122.7 (10)	C30—C27—C28A	130.5 (17)
C21—C20—C25	117.8 (10)	C8A—C27—C8	20.1 (10)
C2—C3—H3	118.5	C8A—C27—C28	113.6 (16)
C4—C3—H3	118.5	C8A—C27—C30	95.7 (14)
C4—C3—C2	123.0 (9)	C8A—C27—C28A	113.9 (17)
C2—C1—C20	178.4 (10)	C30A—C27—C8	121.0 (15)
C15—C16—C19	119.3 (9)	C30A—C27—C28	93.3 (19)
C17—C16—C15	121.5 (9)	C30A—C27—C30	25.7 (14)
C17—C16—C19	119.1 (9)	C30A—C27—C8A	102.2 (15)
O1—C5—C6	123.1 (9)	C30A—C27—C29A	113.4 (14)
O1—C5—C4	121.1 (8)	C30A—C27—C28A	106.2 (13)
C6—C5—C4	115.7 (7)	C29A—C27—C8	109.5 (13)
H7AA—C7—H7AB	107.5	C29A—C27—C28	115.7 (19)
H7AA—C7—H7BC	125.3	C29A—C27—C30	95.1 (15)
H7AA—C7—H7BD	22.0	C29A—C27—C8A	115.7 (13)
H7AB—C7—H7BC	20.5	C29A—C27—C28A	105.3 (13)
H7AB—C7—H7BD	87.6	C28A—C27—C8	99.3 (16)
H7BC—C7—H7BD	107.0	C28A—C27—C28	14 (2)
C6—C7—H7AA	108.5	C16—C19—H19A	109.5
C6—C7—H7AB	108.5	C16—C19—H19B	109.5
C6—C7—H7BC	107.6	C16—C19—H19C	109.5
C6—C7—H7BD	107.6	H19A—C19—H19B	109.5
C6—C7—C8	115.1 (10)	H19A—C19—H19C	109.5
C8—C7—H7AA	108.5	H19B—C19—H19C	109.5
C8—C7—H7AB	108.5	C24—C23—C22	119.5 (11)
C8—C7—H7BC	91.4	C24—C23—C26	119.3 (14)
C8—C7—H7BD	125.3	C22—C23—C26	121.2 (10)
C8A—C7—H7AA	89.0	C7—C8—C27	108.1 (12)
C8A—C7—H7AB	121.3	C7—C8—H8	111.4
C8A—C7—H7BC	107.6	C27—C8—H8	111.4
C8A—C7—H7BD	107.6	C9—C8—C7	100.9 (13)
C8A—C7—C6	118.9 (11)	C9—C8—C27	113.3 (14)
C8A—C7—C8	20.3 (11)	C9—C8—H8	111.4
C1—C2—C3	175.7 (9)	C23—C26—H26A	109.5
C14—C13—C12	119.3 (8)	C23—C26—H26B	109.5
C18—C13—C14	120.8 (9)	C23—C26—H26C	109.5
C18—C13—C12	119.9 (9)	H26A—C26—H26B	109.5
C13—C14—H14	120.3	H26A—C26—H26C	109.5
C13—C14—C15	119.5 (8)	H26B—C26—H26C	109.5
C15—C14—H14	120.3	C4—C9—C8	107.9 (15)
C20—C25—H25	120.2	C4—C9—H9A	110.1
C24—C25—C20	119.6 (8)	C4—C9—H9B	110.1
C24—C25—H25	120.2	C8—C9—H9A	110.1
C7—C6—C5	121.8 (8)	C8—C9—H9B	110.1
C10—C6—C5	114.9 (8)	H9A—C9—H9B	108.4
C10—C6—C7	123.2 (8)	C27—C29—H29A	109.5
C13—C18—H18	120.3	C27—C29—H29B	109.5
C13—C18—C17	119.4 (10)	C27—C29—H29C	109.5
C17—C18—H18	120.3	C27—C28—H28A	109.5
C16—C15—C14	118.3 (9)	C27—C28—H28B	109.5
C16—C15—H15	120.8	C27—C28—H28C	109.5
C14—C15—H15	120.8	C27—C30—H30A	109.5
C3—C4—C5	117.4 (8)	C27—C30—H30B	109.5
C3—C4—C9	127.7 (11)	C27—C30—H30C	109.5
C3—C4—C9A	116.4 (10)	C4—C9A—H9AA	109.4
C5—C4—C9A	124.2 (10)	C4—C9A—H9AB	109.4
C9—C4—C5	113.8 (10)	H9AA—C9A—H9AB	108.0
C9—C4—C9A	26.3 (9)	C8A—C9A—C4	111.1 (15)
C11—C12—C13	175.6 (11)	C8A—C9A—H9AA	109.4
C6—C10—H10	117.5	C8A—C9A—H9AB	109.4
C6—C10—C11	125.0 (9)	C7—C8A—C27	118.2 (14)
C11—C10—H10	117.5	C7—C8A—C9A	125.1 (16)
C16—C17—C18	120.6 (9)	C7—C8A—H8A	97.6
C16—C17—H17	119.7	C27—C8A—H8A	97.6
C18—C17—H17	119.7	C9A—C8A—C27	111.5 (13)
C25—C24—H24	119.4	C9A—C8A—H8A	97.6
C23—C24—C25	121.3 (12)	C27—C30A—H30D	109.5
C23—C24—H24	119.4	C27—C30A—H30E	109.5
C12—C11—C10	177.1 (10)	C27—C30A—H30F	109.5
C20—C21—H21	119.2	H30D—C30A—H30E	109.5
C20—C21—C22	121.6 (12)	H30D—C30A—H30F	109.5
C22—C21—H21	119.2	H30E—C30A—H30F	109.5
C21—C22—H22	120.0	C27—C29A—H29D	109.5
C21—C22—C23	120.0 (9)	C27—C29A—H29E	109.5
C23—C22—H22	120.0	C27—C29A—H29F	109.5
C8—C27—C28	102.9 (16)	H29D—C29A—H29E	109.5
C29—C27—C8	105.3 (14)	H29D—C29A—H29F	109.5
C29—C27—C28	97.7 (18)	H29E—C29A—H29F	109.5
C29—C27—C30	114.6 (17)	C27—C28A—H28D	109.5
C29—C27—C8A	118.4 (15)	C27—C28A—H28E	109.5
C29—C27—C30A	128.5 (17)	C27—C28A—H28F	109.5
C29—C27—C29A	21.1 (13)	H28D—C28A—H28E	109.5
C29—C27—C28A	85.9 (15)	H28D—C28A—H28F	109.5
C30—C27—C8	115.8 (14)	H28E—C28A—H28F	109.5

2-(Furan-2-ylmethylene)-6-(3-phenylprop-2-yn-1-ylidene)cyclohexanone (5a)

Crystal data

C20H16O2	Dx = 1.309 Mg m^−3
Mr = 288.33	Synchrotron radiation, λ = 0.9699 Å
Orthorhombic, Pca21	Cell parameters from 7860 reflections
a = 9.5892 (19) Å	θ = 4–37°
b = 10.145 (2) Å	µ = 0.19 mm^−1
c = 30.080 (6) Å	T = 100 K
V = 2926.2 (10) Å^3	Needle, yellow
Z = 8	0.4 × 0.03 × 0.02 mm
F(000) = 1216

Data collection

Mar CCD diffractometer	3732 reflections with I > 2σ(I)
phi scan	Rint = 0.091
Absorption correction: multi-scan (SCALA; Evans, 2006)	θmax = 38.4°, θmin = 3.3°
Tmin = 0.945, Tmax = 0.999	h = −12→12
15016 measured reflections	k = −12→12
5675 independent reflections	l = −37→37

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.095	w = 1/[σ^2(Fo^2) + (0.010P)^2 + 9.P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.250	(Δ/σ)max < 0.001
S = 1.01	Δρmax = 1.08 e Å^−3
5675 reflections	Δρmin = −0.51 e Å^−3
397 parameters	Absolute structure: Flack x determined using 1267 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.3 (8)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3773 (6)	1.1962 (6)	0.60435 (19)	0.0235 (13)
O2	0.6231 (7)	1.1074 (5)	0.46728 (17)	0.0321 (14)
C1	0.4773 (8)	1.0691 (8)	0.5291 (3)	0.0256 (17)
H1	0.4943	1.1596	0.5352	0.031*
C2	0.4037 (10)	1.0017 (6)	0.5582 (3)	0.016 (2)
C3	0.3486 (9)	1.0772 (8)	0.5991 (3)	0.0280 (18)
C4	0.2561 (10)	1.0075 (7)	0.6306 (3)	0.0170 (19)
C5	0.1852 (9)	1.0857 (9)	0.6609 (3)	0.0286 (18)
H5	0.2042	1.1776	0.6597	0.034*
C6	0.0870 (10)	1.0444 (10)	0.6937 (3)	0.0324 (19)
C7	−0.0009 (10)	1.0200 (9)	0.7211 (3)	0.024 (2)
C8	0.3732 (9)	0.8555 (8)	0.5571 (3)	0.0299 (19)
H8A	0.4492	0.8096	0.5410	0.036*
H8B	0.2854	0.8402	0.5406	0.036*
C9	0.3599 (8)	0.7976 (9)	0.6040 (3)	0.0176 (17)
H9A	0.4459	0.8154	0.6212	0.021*
H9B	0.3469	0.7009	0.6022	0.021*
C10	0.2312 (9)	0.8624 (9)	0.6278 (3)	0.0293 (18)
H10A	0.1451	0.8446	0.6106	0.035*
H10B	0.2199	0.8249	0.6579	0.035*
C11	0.5339 (9)	1.0156 (8)	0.4886 (2)	0.0153 (17)
C12	0.5244 (12)	0.9110 (8)	0.4620 (3)	0.039 (2)
H12	0.4712	0.8339	0.4676	0.047*
C13	0.6084 (13)	0.9348 (11)	0.4233 (3)	0.046 (3)
H13	0.6196	0.8769	0.3987	0.056*
C14	0.6659 (9)	1.0491 (10)	0.4280 (3)	0.028 (2)
H14	0.7287	1.0877	0.4073	0.034*
C15	−0.1028 (9)	1.0083 (7)	0.7571 (3)	0.018 (2)
C16	−0.1557 (9)	0.8874 (9)	0.7712 (3)	0.023 (2)
H16	−0.1214	0.8081	0.7584	0.028*
C17	−0.2606 (9)	0.8816 (9)	0.8046 (3)	0.0231 (19)
H17	−0.2960	0.7988	0.8141	0.028*
C18	−0.3108 (10)	0.9968 (8)	0.8232 (3)	0.023 (2)
H18	−0.3808	0.9928	0.8455	0.027*
C19	−0.2593 (9)	1.1191 (9)	0.8096 (2)	0.0221 (19)
H19	−0.2939	1.1982	0.8224	0.027*
C20	−0.1565 (9)	1.1235 (10)	0.7768 (3)	0.0219 (19)
H20	−0.1215	1.2067	0.7676	0.026*
O1A	0.3796 (7)	0.6955 (7)	0.39805 (19)	0.0315 (15)
O2A	0.1242 (6)	0.6094 (6)	0.5347 (2)	0.0315 (14)
C1A	0.2759 (9)	0.5684 (9)	0.4724 (3)	0.0302 (19)
H1A	0.2629	0.6597	0.4667	0.036*
C2A	0.3485 (9)	0.4997 (6)	0.4401 (3)	0.016 (2)
C3A	0.4058 (9)	0.5748 (9)	0.4033 (3)	0.0282 (18)
C4A	0.5040 (10)	0.5033 (7)	0.3713 (3)	0.017 (2)
C5A	0.5643 (8)	0.5804 (9)	0.3402 (3)	0.0274 (18)
H5A	0.5401	0.6712	0.3392	0.033*
C6A	0.6634 (9)	0.5310 (11)	0.3084 (3)	0.0291 (19)
C7A	0.7484 (11)	0.5075 (7)	0.2786 (3)	0.0202 (19)
C8A	0.3756 (9)	0.3530 (8)	0.4451 (3)	0.0281 (18)
H8AA	0.4591	0.3385	0.4638	0.034*
H8AB	0.2950	0.3102	0.4598	0.034*
C9A	0.3981 (8)	0.2935 (9)	0.3996 (3)	0.0204 (17)
H9AA	0.3128	0.3055	0.3815	0.024*
H9AB	0.4151	0.1977	0.4026	0.024*
C10A	0.5218 (10)	0.3571 (9)	0.3756 (3)	0.033 (2)
H10C	0.6084	0.3383	0.3924	0.040*
H10D	0.5313	0.3178	0.3457	0.040*
C11A	0.2152 (11)	0.5197 (9)	0.5149 (3)	0.029 (2)
C12A	0.2334 (9)	0.4121 (9)	0.5398 (3)	0.0318 (19)
H12A	0.2915	0.3385	0.5338	0.038*
C13A	0.1435 (9)	0.4330 (9)	0.5787 (3)	0.0249 (18)
H13A	0.1247	0.3723	0.6020	0.030*
C14A	0.0934 (12)	0.5561 (10)	0.5743 (3)	0.042 (3)
H14A	0.0419	0.6003	0.5967	0.050*
C15A	0.8550 (10)	0.4980 (7)	0.2462 (3)	0.020 (2)
C16A	0.8974 (9)	0.3730 (9)	0.2290 (3)	0.0210 (19)
H16A	0.8573	0.2938	0.2400	0.025*
C17A	0.9965 (9)	0.3696 (9)	0.1966 (3)	0.0230 (19)
H17A	1.0242	0.2870	0.1846	0.028*
C18A	1.0583 (11)	0.4853 (9)	0.1805 (3)	0.026 (2)
H18A	1.1288	0.4810	0.1584	0.032*
C19A	1.0158 (10)	0.6057 (10)	0.1972 (3)	0.029 (2)
H19A	1.0578	0.6844	0.1865	0.035*
C20A	0.9121 (9)	0.6127 (9)	0.2294 (3)	0.0230 (19)
H20A	0.8807	0.6960	0.2398	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.030 (3)	0.016 (3)	0.024 (3)	−0.004 (3)	0.004 (2)	0.000 (3)
O2	0.060 (4)	0.015 (3)	0.021 (3)	−0.002 (3)	0.013 (3)	0.000 (2)
C1	0.027 (4)	0.023 (4)	0.027 (4)	0.002 (3)	0.003 (3)	0.003 (4)
C2	0.022 (5)	0.016 (5)	0.010 (3)	0.001 (3)	0.004 (3)	0.002 (2)
C3	0.035 (5)	0.021 (4)	0.029 (4)	0.001 (4)	−0.002 (3)	0.005 (3)
C4	0.015 (4)	0.011 (4)	0.025 (5)	−0.004 (3)	−0.001 (3)	0.000 (3)
C5	0.030 (4)	0.030 (5)	0.025 (4)	−0.003 (4)	−0.001 (3)	0.006 (4)
C6	0.036 (5)	0.031 (5)	0.030 (4)	−0.003 (4)	−0.006 (4)	−0.004 (4)
C7	0.023 (5)	0.030 (5)	0.020 (4)	0.003 (3)	0.006 (4)	0.007 (4)
C8	0.037 (5)	0.019 (4)	0.034 (4)	−0.002 (4)	0.005 (4)	0.001 (4)
C9	0.023 (4)	0.015 (4)	0.015 (3)	0.002 (3)	0.002 (3)	−0.002 (3)
C10	0.034 (4)	0.028 (5)	0.026 (4)	0.002 (4)	0.003 (3)	0.002 (3)
C11	0.010 (4)	0.030 (4)	0.006 (3)	−0.001 (3)	0.001 (3)	0.000 (3)
C12	0.081 (7)	0.017 (4)	0.019 (4)	−0.021 (5)	0.015 (4)	−0.006 (3)
C13	0.087 (8)	0.030 (6)	0.022 (4)	0.017 (5)	0.018 (5)	0.000 (4)
C14	0.032 (5)	0.036 (6)	0.017 (4)	0.007 (4)	0.003 (3)	0.002 (4)
C15	0.009 (4)	0.028 (5)	0.016 (4)	−0.002 (3)	0.002 (3)	−0.002 (3)
C16	0.032 (5)	0.020 (5)	0.017 (4)	0.007 (4)	−0.009 (3)	−0.011 (4)
C17	0.028 (4)	0.026 (5)	0.015 (4)	−0.007 (4)	−0.003 (3)	0.001 (3)
C18	0.021 (5)	0.034 (6)	0.014 (4)	0.002 (3)	−0.002 (4)	0.003 (3)
C19	0.026 (4)	0.031 (5)	0.010 (3)	0.007 (4)	0.002 (3)	−0.002 (3)
C20	0.028 (5)	0.022 (5)	0.016 (4)	−0.006 (4)	−0.007 (3)	0.003 (3)
O1A	0.049 (4)	0.022 (4)	0.024 (3)	0.008 (3)	0.005 (3)	0.007 (3)
O2A	0.033 (3)	0.028 (3)	0.034 (3)	0.006 (3)	0.003 (3)	0.004 (3)
C1A	0.034 (5)	0.030 (5)	0.026 (4)	0.007 (4)	−0.005 (3)	0.003 (4)
C2A	0.012 (4)	0.017 (5)	0.017 (4)	−0.001 (3)	−0.009 (3)	0.001 (3)
C3A	0.035 (5)	0.027 (4)	0.023 (4)	−0.004 (4)	−0.003 (3)	−0.001 (3)
C4A	0.016 (4)	0.027 (5)	0.009 (3)	−0.001 (3)	−0.006 (3)	−0.002 (3)
C5A	0.031 (5)	0.025 (4)	0.026 (4)	0.006 (4)	0.001 (3)	0.001 (3)
C6A	0.026 (4)	0.049 (5)	0.012 (4)	−0.006 (4)	0.002 (3)	−0.002 (4)
C7A	0.020 (4)	0.028 (5)	0.013 (3)	−0.002 (3)	−0.008 (3)	0.002 (3)
C8A	0.041 (5)	0.020 (4)	0.024 (4)	0.000 (4)	0.002 (3)	0.000 (3)
C9A	0.028 (4)	0.016 (4)	0.018 (4)	−0.003 (3)	0.000 (3)	−0.006 (3)
C10A	0.041 (5)	0.024 (5)	0.035 (4)	0.002 (4)	0.003 (4)	−0.006 (4)
C11A	0.029 (5)	0.029 (5)	0.029 (5)	0.007 (4)	0.002 (4)	−0.002 (4)
C12A	0.025 (4)	0.031 (5)	0.039 (4)	−0.001 (4)	0.003 (4)	−0.006 (4)
C13A	0.037 (5)	0.017 (4)	0.021 (4)	−0.001 (3)	0.006 (3)	0.007 (3)
C14A	0.087 (8)	0.019 (5)	0.019 (4)	0.021 (5)	0.020 (4)	0.006 (4)
C15A	0.025 (5)	0.021 (5)	0.015 (4)	−0.001 (3)	−0.004 (4)	0.000 (3)
C16A	0.024 (4)	0.016 (4)	0.023 (4)	0.005 (3)	0.009 (3)	0.004 (3)
C17A	0.025 (4)	0.018 (4)	0.026 (4)	0.004 (3)	0.006 (3)	0.000 (4)
C18A	0.028 (5)	0.036 (6)	0.015 (4)	−0.001 (4)	0.004 (4)	0.002 (3)
C19A	0.037 (5)	0.024 (5)	0.027 (4)	−0.009 (4)	0.005 (4)	0.008 (4)
C20A	0.025 (4)	0.020 (5)	0.024 (4)	−0.007 (4)	0.006 (3)	0.001 (4)

Geometric parameters (Å, º)

O1—C3	1.249 (10)	O1A—C3A	1.260 (11)
O2—C11	1.418 (10)	O2A—C11A	1.395 (11)
O2—C14	1.384 (9)	O2A—C14A	1.340 (10)
C1—H1	0.9500	C1A—H1A	0.9500
C1—C2	1.317 (11)	C1A—C2A	1.385 (12)
C1—C11	1.438 (11)	C1A—C11A	1.488 (13)
C2—C3	1.541 (12)	C2A—C3A	1.452 (12)
C2—C8	1.512 (10)	C2A—C8A	1.519 (10)
C3—C4	1.480 (12)	C3A—C4A	1.528 (12)
C4—C5	1.387 (12)	C4A—C5A	1.351 (12)
C4—C10	1.494 (11)	C4A—C10A	1.499 (11)
C5—H5	0.9500	C5A—H5A	0.9500
C5—C6	1.427 (12)	C5A—C6A	1.438 (12)
C6—C7	1.203 (13)	C6A—C7A	1.234 (13)
C7—C15	1.464 (13)	C7A—C15A	1.416 (14)
C8—H8A	0.9900	C8A—H8AA	0.9900
C8—H8B	0.9900	C8A—H8AB	0.9900
C8—C9	1.534 (12)	C8A—C9A	1.513 (11)
C9—H9A	0.9900	C9A—H9AA	0.9900
C9—H9B	0.9900	C9A—H9AB	0.9900
C9—C10	1.570 (11)	C9A—C10A	1.530 (12)
C10—H10A	0.9900	C10A—H10C	0.9900
C10—H10B	0.9900	C10A—H10D	0.9900
C11—C12	1.333 (11)	C11A—C12A	1.335 (13)
C12—H12	0.9500	C12A—H12A	0.9500
C12—C13	1.435 (12)	C12A—C13A	1.466 (11)
C13—H13	0.9500	C13A—H13A	0.9500
C13—C14	1.292 (16)	C13A—C14A	1.345 (14)
C14—H14	0.9500	C14A—H14A	0.9500
C15—C16	1.393 (12)	C15A—C16A	1.428 (12)
C15—C20	1.409 (13)	C15A—C20A	1.382 (12)
C16—H16	0.9500	C16A—H16A	0.9500
C16—C17	1.423 (12)	C16A—C17A	1.363 (11)
C17—H17	0.9500	C17A—H17A	0.9500
C17—C18	1.383 (12)	C17A—C18A	1.401 (13)
C18—H18	0.9500	C18A—H18A	0.9500
C18—C19	1.397 (12)	C18A—C19A	1.382 (14)
C19—H19	0.9500	C19A—H19A	0.9500
C19—C20	1.394 (12)	C19A—C20A	1.390 (12)
C20—H20	0.9500	C20A—H20A	0.9500
C14—O2—C11	106.5 (6)	C14A—O2A—C11A	104.7 (7)
C2—C1—H1	117.6	C2A—C1A—H1A	115.4
C2—C1—C11	124.7 (8)	C2A—C1A—C11A	129.3 (8)
C11—C1—H1	117.6	C11A—C1A—H1A	115.4
C1—C2—C3	117.2 (7)	C1A—C2A—C3A	117.5 (7)
C1—C2—C8	126.7 (8)	C1A—C2A—C8A	120.6 (8)
C8—C2—C3	116.1 (7)	C3A—C2A—C8A	121.7 (8)
O1—C3—C2	120.4 (7)	O1A—C3A—C2A	122.0 (8)
O1—C3—C4	120.8 (7)	O1A—C3A—C4A	120.4 (7)
C4—C3—C2	118.7 (7)	C2A—C3A—C4A	117.6 (7)
C3—C4—C10	121.9 (8)	C5A—C4A—C3A	115.2 (7)
C5—C4—C3	116.3 (7)	C5A—C4A—C10A	125.7 (8)
C5—C4—C10	121.6 (8)	C10A—C4A—C3A	119.0 (8)
C4—C5—H5	116.2	C4A—C5A—H5A	118.6
C4—C5—C6	127.6 (9)	C4A—C5A—C6A	122.9 (8)
C6—C5—H5	116.2	C6A—C5A—H5A	118.6
C7—C6—C5	174.5 (11)	C7A—C6A—C5A	170.5 (10)
C6—C7—C15	171.9 (10)	C6A—C7A—C15A	171.7 (9)
C2—C8—H8A	109.3	C2A—C8A—H8AA	109.9
C2—C8—H8B	109.3	C2A—C8A—H8AB	109.9
C2—C8—C9	111.7 (7)	H8AA—C8A—H8AB	108.3
H8A—C8—H8B	107.9	C9A—C8A—C2A	108.9 (7)
C9—C8—H8A	109.3	C9A—C8A—H8AA	109.9
C9—C8—H8B	109.3	C9A—C8A—H8AB	109.9
C8—C9—H9A	109.9	C8A—C9A—H9AA	109.3
C8—C9—H9B	109.9	C8A—C9A—H9AB	109.3
C8—C9—C10	108.9 (7)	C8A—C9A—C10A	111.6 (7)
H9A—C9—H9B	108.3	H9AA—C9A—H9AB	108.0
C10—C9—H9A	109.9	C10A—C9A—H9AA	109.3
C10—C9—H9B	109.9	C10A—C9A—H9AB	109.3
C4—C10—C9	108.3 (7)	C4A—C10A—C9A	111.7 (7)
C4—C10—H10A	110.0	C4A—C10A—H10C	109.3
C4—C10—H10B	110.0	C4A—C10A—H10D	109.3
C9—C10—H10A	110.0	C9A—C10A—H10C	109.3
C9—C10—H10B	110.0	C9A—C10A—H10D	109.3
H10A—C10—H10B	108.4	H10C—C10A—H10D	107.9
O2—C11—C1	111.3 (7)	O2A—C11A—C1A	113.2 (8)
C12—C11—O2	107.0 (7)	C12A—C11A—O2A	112.0 (9)
C12—C11—C1	141.6 (8)	C12A—C11A—C1A	134.6 (9)
C11—C12—H12	125.8	C11A—C12A—H12A	127.7
C11—C12—C13	108.4 (8)	C11A—C12A—C13A	104.6 (8)
C13—C12—H12	125.8	C13A—C12A—H12A	127.7
C12—C13—H13	126.2	C12A—C13A—H13A	127.3
C14—C13—C12	107.5 (8)	C14A—C13A—C12A	105.4 (7)
C14—C13—H13	126.2	C14A—C13A—H13A	127.3
O2—C14—H14	124.7	O2A—C14A—C13A	112.5 (7)
C13—C14—O2	110.5 (8)	O2A—C14A—H14A	123.7
C13—C14—H14	124.7	C13A—C14A—H14A	123.7
C16—C15—C7	122.7 (8)	C7A—C15A—C16A	121.0 (7)
C16—C15—C20	117.9 (9)	C20A—C15A—C7A	118.7 (7)
C20—C15—C7	119.3 (7)	C20A—C15A—C16A	120.2 (9)
C15—C16—H16	119.7	C15A—C16A—H16A	120.6
C15—C16—C17	120.6 (8)	C17A—C16A—C15A	118.7 (9)
C17—C16—H16	119.7	C17A—C16A—H16A	120.6
C16—C17—H17	120.1	C16A—C17A—H17A	119.3
C18—C17—C16	119.8 (9)	C16A—C17A—C18A	121.4 (9)
C18—C17—H17	120.1	C18A—C17A—H17A	119.3
C17—C18—H18	119.7	C17A—C18A—H18A	120.3
C17—C18—C19	120.6 (9)	C19A—C18A—C17A	119.4 (9)
C19—C18—H18	119.7	C19A—C18A—H18A	120.3
C18—C19—H19	120.5	C18A—C19A—H19A	119.7
C20—C19—C18	119.1 (9)	C18A—C19A—C20A	120.6 (9)
C20—C19—H19	120.5	C20A—C19A—H19A	119.7
C15—C20—H20	119.0	C15A—C20A—C19A	119.7 (9)
C19—C20—C15	122.0 (9)	C15A—C20A—H20A	120.2
C19—C20—H20	119.0	C19A—C20A—H20A	120.2
O1—C3—C4—C5	11.0 (13)	O1A—C3A—C4A—C5A	4.0 (12)
O1—C3—C4—C10	−173.8 (8)	O1A—C3A—C4A—C10A	−173.9 (8)
O2—C11—C12—C13	0.3 (11)	O2A—C11A—C12A—C13A	1.4 (11)
C1—C2—C3—O1	−2.1 (13)	C1A—C2A—C3A—O1A	−7.1 (13)
C1—C2—C3—C4	175.1 (8)	C1A—C2A—C3A—C4A	171.1 (7)
C1—C2—C8—C9	148.5 (9)	C1A—C2A—C8A—C9A	156.0 (8)
C1—C11—C12—C13	173.9 (11)	C1A—C11A—C12A—C13A	177.2 (11)
C2—C1—C11—O2	−172.2 (8)	C2A—C1A—C11A—O2A	−167.1 (8)
C2—C1—C11—C12	14.3 (19)	C2A—C1A—C11A—C12A	17.1 (19)
C2—C3—C4—C5	−166.2 (8)	C2A—C3A—C4A—C5A	−174.2 (7)
C2—C3—C4—C10	9.0 (13)	C2A—C3A—C4A—C10A	8.0 (12)
C2—C8—C9—C10	63.7 (9)	C2A—C8A—C9A—C10A	59.4 (9)
C3—C2—C8—C9	−28.3 (10)	C3A—C2A—C8A—C9A	−28.6 (11)
C3—C4—C5—C6	177.8 (8)	C3A—C4A—C5A—C6A	177.6 (7)
C3—C4—C10—C9	25.1 (12)	C3A—C4A—C10A—C9A	22.1 (12)
C5—C4—C10—C9	−160.0 (8)	C5A—C4A—C10A—C9A	−155.5 (9)
C7—C15—C16—C17	−176.4 (9)	C7A—C15A—C16A—C17A	177.4 (9)
C7—C15—C20—C19	176.5 (9)	C7A—C15A—C20A—C19A	−179.3 (9)
C8—C2—C3—O1	175.0 (8)	C8A—C2A—C3A—O1A	177.4 (8)
C8—C2—C3—C4	−7.8 (12)	C8A—C2A—C3A—C4A	−4.5 (12)
C8—C9—C10—C4	−60.7 (9)	C8A—C9A—C10A—C4A	−57.1 (10)
C10—C4—C5—C6	2.6 (14)	C10A—C4A—C5A—C6A	−4.6 (14)
C11—O2—C14—C13	1.9 (10)	C11A—O2A—C14A—C13A	−7.8 (12)
C11—C1—C2—C3	−178.5 (7)	C11A—C1A—C2A—C3A	−175.2 (8)
C11—C1—C2—C8	4.8 (15)	C11A—C1A—C2A—C8A	0.3 (14)
C11—C12—C13—C14	0.9 (13)	C11A—C12A—C13A—C14A	−5.9 (11)
C12—C13—C14—O2	−1.7 (12)	C12A—C13A—C14A—O2A	8.7 (12)
C14—O2—C11—C1	−177.0 (7)	C14A—O2A—C11A—C1A	−173.1 (9)
C14—O2—C11—C12	−1.3 (9)	C14A—O2A—C11A—C12A	3.6 (11)
C15—C16—C17—C18	0.0 (13)	C15A—C16A—C17A—C18A	1.1 (13)
C16—C15—C20—C19	0.0 (13)	C16A—C15A—C20A—C19A	−3.0 (14)
C16—C17—C18—C19	0.0 (14)	C16A—C17A—C18A—C19A	−1.5 (15)
C17—C18—C19—C20	0.0 (13)	C17A—C18A—C19A—C20A	−0.4 (15)
C18—C19—C20—C15	0.0 (12)	C18A—C19A—C20A—C15A	2.6 (14)
C20—C15—C16—C17	0.0 (13)	C20A—C15A—C16A—C17A	1.2 (14)

6-(3-Butylprop-2-yn-1-ylidene)-2-(furan-2-ylmethylene)cyclohexanone (5b)

Crystal data

C18H20O2	Z = 2
Mr = 268.34	F(000) = 288
Triclinic, P1	Dx = 1.203 Mg m^−3
a = 9.2801 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5498 (14) Å	Cell parameters from 2852 reflections
c = 9.6407 (14) Å	θ = 2.3–34.7°
α = 84.218 (3)°	µ = 0.08 mm^−1
β = 70.882 (3)°	T = 120 K
γ = 66.632 (3)°	Prism, yellow
V = 740.63 (19) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

Bruker SMART APEX CCD area detector diffractometer	6779 independent reflections
Radiation source: sealed tube	4496 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 8 pixels mm^-1	θmax = 36.1°, θmin = 2.3°
ω and φ scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −15→15
Tmin = 0.669, Tmax = 0.747	l = −15→15
13735 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.150P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
6779 reflections	Δρmax = 0.45 e Å^−3
182 parameters	Δρmin = −0.32 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.23655 (10)	0.69376 (8)	0.12731 (9)	0.02436 (17)
O2	0.06610 (10)	0.31249 (8)	0.04610 (9)	0.02500 (17)
C1	0.33819 (12)	0.58373 (11)	0.16766 (11)	0.01795 (18)
C2	0.46380 (12)	0.60414 (11)	0.21891 (11)	0.01820 (18)
C3	0.60114 (13)	0.46600 (12)	0.24468 (13)	0.0239 (2)
H3A	0.6485	0.4939	0.3108	0.029*
H3B	0.6898	0.4268	0.1502	0.029*
C4	0.53785 (15)	0.34239 (12)	0.31322 (13)	0.0248 (2)
H4A	0.4514	0.3808	0.4090	0.030*
H4B	0.6297	0.2524	0.3310	0.030*
C5	0.46633 (13)	0.29535 (11)	0.21279 (12)	0.0210 (2)
H5A	0.5576	0.2404	0.1247	0.025*
H5B	0.4148	0.2239	0.2649	0.025*
C6	0.33968 (12)	0.42801 (11)	0.16475 (11)	0.01714 (18)
C7	0.22526 (12)	0.41645 (11)	0.11416 (11)	0.01856 (18)
H7	0.1503	0.5099	0.0905	0.022*
C8	0.20164 (12)	0.28237 (11)	0.09137 (11)	0.01880 (18)
C9	0.27716 (13)	0.12861 (11)	0.10131 (12)	0.0217 (2)
H9	0.3737	0.0765	0.1294	0.026*
C10	0.18437 (14)	0.06108 (12)	0.06178 (13)	0.0259 (2)
H10	0.2061	−0.0447	0.0588	0.031*
C11	0.05936 (15)	0.17637 (13)	0.02933 (14)	0.0282 (2)
H11	−0.0225	0.1639	−0.0012	0.034*
C12	0.44379 (13)	0.74814 (12)	0.24116 (12)	0.0217 (2)
H12	0.3501	0.8275	0.2242	0.026*
C13	0.55011 (14)	0.79231 (12)	0.28780 (12)	0.0232 (2)
C14	0.63463 (14)	0.83827 (13)	0.32581 (13)	0.0250 (2)
C15	0.73884 (15)	0.88956 (13)	0.37614 (14)	0.0270 (2)
H15A	0.6674	0.9664	0.4573	0.032*
H15B	0.7952	0.9402	0.2946	0.032*
C16	0.86873 (14)	0.76120 (13)	0.42901 (13)	0.0250 (2)
H16A	0.8134	0.7083	0.5088	0.030*
H16B	0.9435	0.6861	0.3471	0.030*
C17	0.96963 (16)	0.82046 (16)	0.48471 (15)	0.0330 (3)
H17A	0.8937	0.9013	0.5613	0.040*
H17B	1.0308	0.8670	0.4027	0.040*
C18	1.09177 (17)	0.69700 (19)	0.54821 (16)	0.0439 (4)
H18A	1.1686	0.6173	0.4726	0.066*
H18B	1.0318	0.6525	0.6314	0.066*
H18C	1.1539	0.7414	0.5817	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0267 (4)	0.0158 (3)	0.0373 (4)	−0.0081 (3)	−0.0200 (3)	0.0052 (3)
O2	0.0258 (4)	0.0167 (3)	0.0397 (5)	−0.0077 (3)	−0.0207 (3)	0.0030 (3)
C1	0.0185 (4)	0.0170 (4)	0.0197 (4)	−0.0070 (3)	−0.0080 (3)	0.0020 (3)
C2	0.0188 (4)	0.0185 (4)	0.0192 (4)	−0.0078 (3)	−0.0082 (4)	0.0029 (3)
C3	0.0221 (5)	0.0211 (5)	0.0335 (6)	−0.0082 (4)	−0.0162 (4)	0.0046 (4)
C4	0.0293 (5)	0.0206 (5)	0.0306 (6)	−0.0101 (4)	−0.0184 (5)	0.0076 (4)
C5	0.0235 (5)	0.0150 (4)	0.0264 (5)	−0.0063 (4)	−0.0123 (4)	0.0032 (4)
C6	0.0186 (4)	0.0152 (4)	0.0185 (4)	−0.0068 (3)	−0.0070 (3)	0.0019 (3)
C7	0.0195 (4)	0.0148 (4)	0.0217 (5)	−0.0062 (3)	−0.0076 (4)	0.0017 (3)
C8	0.0181 (4)	0.0171 (4)	0.0234 (5)	−0.0066 (3)	−0.0097 (4)	0.0015 (3)
C9	0.0218 (5)	0.0161 (4)	0.0296 (5)	−0.0058 (4)	−0.0132 (4)	0.0014 (4)
C10	0.0291 (5)	0.0163 (4)	0.0377 (6)	−0.0085 (4)	−0.0178 (5)	0.0011 (4)
C11	0.0312 (6)	0.0200 (5)	0.0434 (7)	−0.0118 (4)	−0.0219 (5)	0.0015 (4)
C12	0.0230 (5)	0.0206 (5)	0.0257 (5)	−0.0096 (4)	−0.0119 (4)	0.0025 (4)
C13	0.0259 (5)	0.0206 (5)	0.0265 (5)	−0.0102 (4)	−0.0115 (4)	0.0020 (4)
C14	0.0272 (5)	0.0237 (5)	0.0281 (5)	−0.0111 (4)	−0.0120 (4)	0.0005 (4)
C15	0.0291 (6)	0.0259 (5)	0.0338 (6)	−0.0138 (4)	−0.0150 (5)	−0.0015 (4)
C16	0.0226 (5)	0.0272 (5)	0.0284 (5)	−0.0115 (4)	−0.0091 (4)	−0.0007 (4)
C17	0.0296 (6)	0.0426 (7)	0.0345 (6)	−0.0175 (5)	−0.0144 (5)	−0.0028 (5)
C18	0.0293 (7)	0.0655 (10)	0.0373 (7)	−0.0153 (7)	−0.0158 (6)	0.0046 (7)

Geometric parameters (Å, º)

O1—C1	1.2317 (12)	C9—C10	1.4169 (15)
O2—C8	1.3793 (12)	C10—H10	0.9500
O2—C11	1.3540 (13)	C10—C11	1.3457 (15)
C1—C2	1.4892 (14)	C11—H11	0.9500
C1—C6	1.4847 (13)	C12—H12	0.9500
C2—C3	1.4947 (14)	C12—C13	1.4187 (15)
C2—C12	1.3424 (14)	C13—C14	1.1982 (15)
C3—H3A	0.9900	C14—C15	1.4635 (15)
C3—H3B	0.9900	C15—H15A	0.9900
C3—C4	1.5211 (15)	C15—H15B	0.9900
C4—H4A	0.9900	C15—C16	1.5231 (16)
C4—H4B	0.9900	C16—H16A	0.9900
C4—C5	1.5248 (15)	C16—H16B	0.9900
C5—H5A	0.9900	C16—C17	1.5154 (16)
C5—H5B	0.9900	C17—H17A	0.9900
C5—C6	1.5026 (13)	C17—H17B	0.9900
C6—C7	1.3494 (14)	C17—C18	1.5161 (19)
C7—H7	0.9500	C18—H18A	0.9800
C7—C8	1.4306 (14)	C18—H18B	0.9800
C8—C9	1.3623 (14)	C18—H18C	0.9800
C9—H9	0.9500
C11—O2—C8	106.96 (8)	C10—C9—H9	126.5
O1—C1—C2	120.48 (9)	C9—C10—H10	126.8
O1—C1—C6	120.95 (9)	C11—C10—C9	106.45 (9)
C6—C1—C2	118.56 (8)	C11—C10—H10	126.8
C1—C2—C3	119.03 (9)	O2—C11—H11	124.6
C12—C2—C1	116.87 (9)	C10—C11—O2	110.78 (10)
C12—C2—C3	124.09 (9)	C10—C11—H11	124.6
C2—C3—H3A	109.6	C2—C12—H12	117.1
C2—C3—H3B	109.6	C2—C12—C13	125.79 (10)
C2—C3—C4	110.44 (9)	C13—C12—H12	117.1
H3A—C3—H3B	108.1	C14—C13—C12	176.18 (12)
C4—C3—H3A	109.6	C13—C14—C15	177.80 (12)
C4—C3—H3B	109.6	C14—C15—H15A	108.8
C3—C4—H4A	109.5	C14—C15—H15B	108.8
C3—C4—H4B	109.5	C14—C15—C16	113.67 (9)
C3—C4—C5	110.80 (9)	H15A—C15—H15B	107.7
H4A—C4—H4B	108.1	C16—C15—H15A	108.8
C5—C4—H4A	109.5	C16—C15—H15B	108.8
C5—C4—H4B	109.5	C15—C16—H16A	109.3
C4—C5—H5A	108.9	C15—C16—H16B	109.3
C4—C5—H5B	108.9	H16A—C16—H16B	107.9
H5A—C5—H5B	107.7	C17—C16—C15	111.74 (10)
C6—C5—C4	113.29 (8)	C17—C16—H16A	109.3
C6—C5—H5A	108.9	C17—C16—H16B	109.3
C6—C5—H5B	108.9	C16—C17—H17A	109.0
C1—C6—C5	119.92 (9)	C16—C17—H17B	109.0
C7—C6—C1	115.73 (8)	C16—C17—C18	113.00 (12)
C7—C6—C5	124.33 (9)	H17A—C17—H17B	107.8
C6—C7—H7	115.7	C18—C17—H17A	109.0
C6—C7—C8	128.70 (9)	C18—C17—H17B	109.0
C8—C7—H7	115.7	C17—C18—H18A	109.5
O2—C8—C7	113.56 (8)	C17—C18—H18B	109.5
C9—C8—O2	108.80 (9)	C17—C18—H18C	109.5
C9—C8—C7	137.64 (10)	H18A—C18—H18B	109.5
C8—C9—H9	126.5	H18A—C18—H18C	109.5
C8—C9—C10	107.02 (9)	H18B—C18—H18C	109.5