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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(CPh) atoms and thus stabilize CPh—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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015838/jx3023sup1.cif
Contains datablocks 3a, 3b, 3c, 3d, 3e, 3f, 5a, 5b, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233asup2.hkl
Contains datablock 3a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233bsup3.hkl
Contains datablock 3b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233csup4.hkl
Contains datablock 3c

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233dsup5.hkl
Contains datablock 3d

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233esup6.hkl
Contains datablock 3e

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30233fsup7.hkl
Contains datablock 3f

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30235asup8.hkl
Contains datablock 5a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015838/jx30235bsup9.hkl
Contains datablock 5b

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233asup10.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233bsup11.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233csup12.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233dsup13.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30233esup14.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618015838/jx30235asup15.cml
Supplementary material

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618015838/jx3023sup16.pdf
Additional synthesis and analytical details

CCDC references: 1877738; 1848662; 1848661; 1848660; 1848659; 1848658; 1848657; 1848656

Computing details top

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) top
Crystal data top
C23H16OF(000) = 648
Mr = 308.36Dx = 1.202 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.723 (6) ÅCell parameters from 2200 reflections
b = 27.11 (3) Åθ = 2.4–29.3°
c = 10.984 (12) ŵ = 0.07 mm1
β = 89.55 (3)°T = 200 K
V = 1704 (3) Å3Plate, light brown
Z = 40.42 × 0.18 × 0.04 mm
Data collection top
Bruker SMART APEX CCD area detector
diffractometer
2173 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.203
phi and ω scansθmax = 30.2°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 77
Tmin = 0.459, Tmax = 0.746k = 3837
18018 measured reflectionsl = 1414
4776 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.084H-atom parameters constrained
wR(F2) = 0.191 w = 1/[σ2(Fo2) + (0.055P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4776 reflectionsΔρmax = 0.26 e Å3
217 parametersΔρmin = 0.20 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2923 (3)0.40975 (7)0.93814 (16)0.0546 (5)
C10.3399 (4)0.39016 (9)0.8400 (2)0.0399 (6)
C20.5325 (4)0.35511 (9)0.8183 (2)0.0391 (6)
C30.5241 (4)0.33729 (10)0.6890 (2)0.0465 (6)
H3A0.49420.30130.68650.056*
H3B0.67410.34410.64670.056*
C40.3234 (5)0.36565 (13)0.6278 (3)0.0628 (8)
H4A0.38420.38640.56060.075*
H4B0.20690.34240.59450.075*
C50.2150 (4)0.39702 (9)0.7248 (2)0.0401 (6)
C60.6908 (4)0.34281 (9)0.9030 (2)0.0456 (6)
H60.68220.35820.98050.055*
C70.8692 (4)0.30784 (10)0.8810 (2)0.0453 (6)
C81.0121 (4)0.27709 (10)0.8562 (2)0.0456 (6)
C91.1707 (4)0.23891 (9)0.8201 (2)0.0420 (6)
C101.3658 (4)0.22711 (10)0.8903 (3)0.0503 (7)
H101.39280.24410.96460.060*
C111.5189 (5)0.19091 (11)0.8520 (3)0.0605 (8)
H111.65150.18300.89960.073*
C121.4789 (5)0.16640 (11)0.7448 (3)0.0637 (8)
H121.58470.14150.71850.076*
C131.2865 (5)0.17754 (11)0.6746 (3)0.0620 (8)
H131.25980.16010.60110.074*
C141.1343 (4)0.21375 (10)0.7112 (3)0.0539 (7)
H141.00350.22170.66220.065*
C150.0336 (4)0.42770 (9)0.7106 (2)0.0462 (6)
H150.02560.44500.77950.055*
C160.0728 (4)0.43521 (9)0.5962 (3)0.0454 (6)
C170.1442 (4)0.44076 (9)0.4942 (3)0.0452 (6)
C180.2073 (4)0.44766 (9)0.3686 (2)0.0411 (6)
C190.0521 (4)0.43317 (10)0.2787 (3)0.0503 (7)
H190.09060.41770.30050.060*
C200.1031 (5)0.44101 (11)0.1563 (3)0.0594 (8)
H200.00510.43140.09480.071*
C210.3104 (5)0.46277 (11)0.1255 (3)0.0573 (8)
H210.34540.46820.04210.069*
C220.4666 (4)0.47669 (10)0.2128 (3)0.0553 (7)
H220.61000.49160.18990.066*
C230.4185 (4)0.46941 (10)0.3345 (3)0.0488 (7)
H230.52870.47920.39500.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0676 (11)0.0593 (12)0.0370 (11)0.0160 (9)0.0094 (8)0.0083 (9)
C10.0442 (13)0.0405 (14)0.0350 (14)0.0017 (11)0.0011 (11)0.0018 (11)
C20.0393 (12)0.0397 (14)0.0385 (14)0.0018 (11)0.0056 (11)0.0005 (11)
C30.0496 (13)0.0512 (16)0.0386 (15)0.0019 (12)0.0051 (11)0.0030 (12)
C40.0601 (16)0.088 (2)0.0401 (16)0.0195 (16)0.0116 (13)0.0083 (16)
C50.0421 (12)0.0454 (14)0.0328 (13)0.0017 (11)0.0069 (10)0.0012 (11)
C60.0489 (13)0.0464 (15)0.0416 (15)0.0023 (12)0.0082 (12)0.0032 (12)
C70.0421 (13)0.0522 (16)0.0419 (15)0.0009 (13)0.0100 (11)0.0008 (13)
C80.0422 (13)0.0509 (16)0.0438 (15)0.0028 (13)0.0092 (11)0.0034 (13)
C90.0432 (13)0.0407 (14)0.0422 (15)0.0032 (11)0.0009 (11)0.0048 (12)
C100.0527 (15)0.0538 (17)0.0445 (16)0.0018 (13)0.0045 (12)0.0050 (13)
C110.0592 (16)0.0630 (19)0.059 (2)0.0146 (15)0.0024 (14)0.0166 (16)
C120.0734 (19)0.0492 (18)0.068 (2)0.0116 (15)0.0148 (17)0.0068 (16)
C130.0739 (19)0.0573 (18)0.0546 (19)0.0060 (16)0.0033 (16)0.0134 (15)
C140.0528 (15)0.0570 (17)0.0520 (18)0.0025 (14)0.0049 (13)0.0069 (14)
C150.0502 (14)0.0456 (15)0.0430 (16)0.0017 (12)0.0098 (11)0.0019 (12)
C160.0483 (14)0.0418 (15)0.0462 (17)0.0036 (11)0.0151 (12)0.0012 (12)
C170.0434 (13)0.0420 (14)0.0505 (17)0.0018 (11)0.0138 (12)0.0003 (13)
C180.0379 (12)0.0403 (14)0.0453 (16)0.0031 (11)0.0139 (11)0.0014 (12)
C190.0396 (13)0.0560 (17)0.0555 (18)0.0008 (12)0.0102 (12)0.0050 (14)
C200.0580 (17)0.069 (2)0.0512 (19)0.0082 (15)0.0041 (14)0.0093 (16)
C210.0654 (18)0.0654 (19)0.0413 (16)0.0139 (15)0.0199 (14)0.0037 (15)
C220.0502 (15)0.0617 (19)0.0545 (19)0.0036 (14)0.0229 (14)0.0064 (15)
C230.0409 (13)0.0570 (17)0.0486 (16)0.0036 (12)0.0106 (11)0.0035 (14)
Geometric parameters (Å, º) top
O1—C11.230 (3)C11—C121.373 (4)
C1—C21.473 (3)C12—H120.9500
C1—C51.471 (4)C12—C131.382 (4)
C2—C31.501 (4)C13—H130.9500
C2—C61.345 (3)C13—C141.371 (4)
C3—H3A0.9900C14—H140.9500
C3—H3B0.9900C15—H150.9500
C3—C41.541 (4)C15—C161.415 (4)
C4—H4A0.9900C16—C171.204 (4)
C4—H4B0.9900C17—C181.442 (4)
C4—C51.494 (4)C18—C191.379 (4)
C5—C151.341 (3)C18—C231.398 (3)
C6—H60.9500C19—H190.9500
C6—C71.413 (4)C19—C201.394 (4)
C7—C81.198 (3)C20—H200.9500
C8—C91.430 (4)C20—C211.370 (4)
C9—C101.399 (4)C21—H210.9500
C9—C141.394 (4)C21—C221.359 (4)
C10—H100.9500C22—H220.9500
C10—C111.379 (4)C22—C231.381 (4)
C11—H110.9500C23—H230.9500
O1—C1—C2125.5 (2)C12—C11—H11120.1
O1—C1—C5126.4 (2)C11—C12—H12119.6
C5—C1—C2108.1 (2)C11—C12—C13120.8 (3)
C1—C2—C3109.3 (2)C13—C12—H12119.6
C6—C2—C1123.7 (2)C12—C13—H13120.0
C6—C2—C3126.9 (2)C14—C13—C12120.0 (3)
C2—C3—H3A110.5C14—C13—H13120.0
C2—C3—H3B110.5C9—C14—H14119.9
C2—C3—C4106.4 (2)C13—C14—C9120.2 (3)
H3A—C3—H3B108.6C13—C14—H14119.9
C4—C3—H3A110.5C5—C15—H15118.9
C4—C3—H3B110.5C5—C15—C16122.1 (2)
C3—C4—H4A110.5C16—C15—H15118.9
C3—C4—H4B110.5C17—C16—C15174.2 (3)
H4A—C4—H4B108.7C16—C17—C18174.7 (3)
C5—C4—C3106.2 (2)C19—C18—C17118.9 (2)
C5—C4—H4A110.5C19—C18—C23118.8 (3)
C5—C4—H4B110.5C23—C18—C17122.3 (2)
C1—C5—C4109.9 (2)C18—C19—H19119.7
C15—C5—C1124.1 (2)C18—C19—C20120.5 (2)
C15—C5—C4126.0 (2)C20—C19—H19119.7
C2—C6—H6118.7C19—C20—H20120.2
C2—C6—C7122.5 (2)C21—C20—C19119.5 (3)
C7—C6—H6118.7C21—C20—H20120.2
C8—C7—C6175.8 (3)C20—C21—H21119.6
C7—C8—C9175.7 (3)C22—C21—C20120.7 (3)
C10—C9—C8121.3 (2)C22—C21—H21119.6
C14—C9—C8119.5 (2)C21—C22—H22119.7
C14—C9—C10119.1 (2)C21—C22—C23120.6 (3)
C9—C10—H10119.9C23—C22—H22119.7
C11—C10—C9120.2 (3)C18—C23—H23120.0
C11—C10—H10119.9C22—C23—C18119.9 (3)
C10—C11—H11120.1C22—C23—H23120.0
C12—C11—C10119.7 (3)
O1—C1—C2—C3176.7 (2)C8—C9—C10—C11178.5 (2)
O1—C1—C2—C64.7 (4)C8—C9—C14—C13179.1 (2)
O1—C1—C5—C4178.4 (2)C9—C10—C11—C120.1 (4)
O1—C1—C5—C152.6 (4)C10—C9—C14—C130.8 (4)
C1—C2—C3—C43.4 (3)C10—C11—C12—C130.1 (4)
C1—C2—C6—C7177.8 (2)C11—C12—C13—C140.7 (4)
C1—C5—C15—C16176.3 (2)C12—C13—C14—C91.0 (4)
C2—C1—C5—C41.1 (3)C14—C9—C10—C110.2 (4)
C2—C1—C5—C15178.0 (2)C17—C18—C19—C20177.5 (2)
C2—C3—C4—C52.7 (3)C17—C18—C23—C22177.7 (2)
C3—C2—C6—C73.7 (4)C18—C19—C20—C210.8 (4)
C3—C4—C5—C11.0 (3)C19—C18—C23—C221.0 (4)
C3—C4—C5—C15180.0 (2)C19—C20—C21—C220.1 (4)
C4—C5—C15—C162.6 (4)C20—C21—C22—C230.4 (4)
C5—C1—C2—C32.8 (3)C21—C22—C23—C180.2 (4)
C5—C1—C2—C6175.9 (2)C23—C18—C19—C201.3 (4)
C6—C2—C3—C4175.2 (2)
2,5-Bis[3-(4-bromophenyl)prop-2-yn-1-ylidene]cyclopentanone (3b) top
Crystal data top
C23H14Br2ODx = 1.665 Mg m3
Mr = 466.16Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Abm2Cell parameters from 6354 reflections
a = 7.098 (3) Åθ = 2–31°
b = 42.72 (2) ŵ = 4.37 mm1
c = 6.135 (3) ÅT = 120 K
V = 1860.1 (15) Å3Needle, yellow
Z = 40.1 × 0.08 × 0.07 mm
F(000) = 920
Data collection top
Bruker SMART APEX CCD area detector
diffractometer
1928 reflections with I > 2σ(I)
phi and ω scansRint = 0.088
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
θmax = 30.5°, θmin = 1.9°
Tmin = 0.664, Tmax = 0.737h = 1010
9371 measured reflectionsk = 5960
2642 independent reflectionsl = 87
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.064 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.165(Δ/σ)max = 0.001
S = 0.97Δρmax = 1.93 e Å3
2642 reflectionsΔρmin = 1.09 e Å3
121 parametersAbsolute structure: Flack x determined using 608 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.30 (2)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br20.20037 (10)0.52932 (2)0.27597 (19)0.0254 (2)
C200.1758 (11)0.5942 (2)0.1799 (16)0.0211 (17)
H200.12500.59630.32250.025*
C190.2287 (12)0.56488 (19)0.0978 (15)0.0180 (16)
C90.2839 (11)0.6441 (2)0.3037 (16)0.0215 (17)
C160.2694 (11)0.61730 (19)0.1658 (13)0.0181 (17)
C210.2001 (11)0.62021 (19)0.0451 (15)0.0195 (16)
H210.16860.64040.09880.023*
C170.3224 (9)0.58749 (17)0.2436 (18)0.0176 (15)
H170.37370.58530.38580.021*
C70.3169 (12)0.6929 (2)0.5574 (14)0.0191 (16)
H70.36780.69050.69970.023*
C180.2993 (11)0.56113 (19)0.1114 (14)0.0192 (15)
H180.33150.54090.16400.023*
C80.2953 (13)0.6661 (2)0.4269 (17)0.0252 (19)
O10.3698 (13)0.75000.8151 (15)0.022 (2)
C50.3090 (15)0.75000.626 (2)0.014 (2)
C60.2691 (11)0.7219 (2)0.4905 (15)0.0177 (15)
C230.1891 (13)0.7318 (2)0.2744 (12)0.026 (2)
H23A0.05930.72370.25670.031*
H23B0.26760.72370.15350.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br20.0244 (4)0.0226 (4)0.0291 (4)0.0021 (3)0.0013 (6)0.0085 (5)
C200.015 (4)0.029 (4)0.019 (4)0.004 (3)0.003 (3)0.002 (3)
C190.015 (4)0.021 (4)0.017 (4)0.003 (3)0.007 (3)0.000 (3)
C90.018 (4)0.024 (4)0.023 (4)0.000 (3)0.004 (3)0.003 (3)
C160.014 (3)0.022 (4)0.018 (4)0.007 (3)0.007 (3)0.000 (3)
C210.015 (4)0.020 (4)0.024 (4)0.001 (3)0.005 (3)0.003 (3)
C170.016 (3)0.025 (3)0.012 (4)0.001 (2)0.001 (3)0.000 (4)
C70.019 (4)0.026 (4)0.013 (4)0.001 (3)0.002 (3)0.002 (3)
C180.019 (4)0.019 (3)0.019 (4)0.001 (3)0.000 (3)0.000 (3)
C80.026 (5)0.023 (4)0.027 (5)0.001 (4)0.001 (4)0.002 (3)
O10.017 (5)0.033 (5)0.015 (4)0.0000.001 (4)0.000
C50.007 (5)0.020 (5)0.014 (5)0.0000.005 (4)0.000
C60.016 (3)0.027 (4)0.010 (4)0.006 (3)0.002 (3)0.001 (3)
C230.039 (5)0.032 (4)0.007 (4)0.002 (4)0.005 (3)0.000 (3)
Geometric parameters (Å, º) top
Br2—C191.882 (8)C7—H70.9500
C20—H200.9500C7—C81.406 (12)
C20—C191.400 (12)C7—C61.346 (12)
C20—C211.397 (12)C18—H180.9500
C19—C181.387 (12)O1—C51.237 (14)
C9—C161.427 (12)C5—C61.489 (12)
C9—C81.209 (13)C5—C6i1.489 (12)
C16—C211.390 (12)C6—C231.503 (12)
C16—C171.411 (11)C23—C23i1.556 (18)
C21—H210.9500C23—H23A0.9900
C17—H170.9500C23—H23B0.9900
C17—C181.398 (12)
C19—C20—H20121.1C6—C7—C8123.2 (8)
C21—C20—H20121.1C19—C18—C17119.1 (8)
C21—C20—C19117.7 (8)C19—C18—H18120.4
C20—C19—Br2118.9 (7)C17—C18—H18120.4
C18—C19—Br2118.9 (6)C9—C8—C7175.5 (10)
C18—C19—C20122.2 (8)O1—C5—C6i126.1 (6)
C8—C9—C16177.7 (10)O1—C5—C6126.1 (6)
C21—C16—C9120.4 (8)C6—C5—C6i107.7 (11)
C21—C16—C17119.3 (8)C7—C6—C5121.6 (8)
C17—C16—C9120.3 (8)C7—C6—C23128.5 (8)
C20—C21—H21119.2C5—C6—C23109.7 (8)
C16—C21—C20121.6 (8)C6—C23—C23i106.4 (5)
C16—C21—H21119.2C6—C23—H23A110.5
C16—C17—H17120.0C6—C23—H23B110.5
C18—C17—C16120.0 (9)C23i—C23—H23A110.5
C18—C17—H17120.0C23i—C23—H23B110.5
C8—C7—H7118.4H23A—C23—H23B108.6
C6—C7—H7118.4
Symmetry code: (i) x, y+3/2, z.
2,6-Bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone (3c) top
Crystal data top
C24H18OF(000) = 680
Mr = 322.38Dx = 1.231 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.498 (4) ÅCell parameters from 160 reflections
b = 27.52 (2) Åθ = 3.5–19.9°
c = 13.885 (9) ŵ = 0.07 mm1
β = 124.09 (3)°T = 120 K
V = 1740 (2) Å3Needle, orange
Z = 40.5 × 0.01 × 0.01 mm
Data collection top
Bruker SMART APEX CCD area detector
diffractometer
2379 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.250
phi and ω scansθmax = 30.8°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 77
Tmin = 0.549, Tmax = 0.892k = 3939
31410 measured reflectionsl = 1919
5336 independent reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.085H-atom parameters constrained
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.010P)2 + 0.2P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
5336 reflectionsΔρmax = 0.35 e Å3
226 parametersΔρmin = 0.29 e Å3
0 restraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2215 (3)0.38803 (5)0.43170 (12)0.0283 (4)
C10.0203 (5)0.49168 (8)0.69236 (19)0.0253 (5)
C20.0487 (5)0.46686 (8)0.64072 (19)0.0255 (5)
C30.1269 (5)0.43898 (8)0.57618 (19)0.0246 (5)
H30.00250.44130.49380.030*
C40.3596 (5)0.40976 (7)0.62070 (18)0.0215 (5)
C50.3993 (5)0.38318 (7)0.53697 (18)0.0213 (5)
C60.6545 (4)0.35037 (7)0.58313 (18)0.0208 (5)
C70.6980 (5)0.32912 (8)0.50745 (18)0.0242 (5)
H70.56340.33650.42740.029*
C80.9293 (5)0.29653 (8)0.53765 (18)0.0256 (5)
C91.1210 (5)0.26811 (8)0.56295 (18)0.0260 (5)
C100.0992 (5)0.52097 (8)0.75603 (19)0.0245 (5)
C110.3717 (5)0.54333 (8)0.7005 (2)0.0289 (6)
H110.50680.53960.61890.035*
C120.4488 (5)0.57078 (8)0.7620 (2)0.0350 (6)
H120.63720.58560.72300.042*
C130.2541 (6)0.57689 (9)0.8797 (2)0.0408 (7)
H130.30680.59630.92190.049*
C140.0170 (6)0.55503 (10)0.9364 (2)0.0468 (7)
H140.15060.55911.01800.056*
C150.0961 (6)0.52717 (9)0.8753 (2)0.0387 (7)
H150.28420.51220.91490.046*
C161.3528 (5)0.23453 (7)0.59615 (19)0.0233 (5)
C171.3961 (5)0.21501 (8)0.5141 (2)0.0287 (6)
H171.26900.22390.43460.034*
C181.6227 (5)0.18283 (8)0.5479 (2)0.0346 (6)
H181.64920.16940.49130.042*
C191.8114 (5)0.16999 (8)0.6633 (2)0.0349 (6)
H191.96830.14800.68630.042*
C201.7708 (5)0.18927 (8)0.7450 (2)0.0334 (6)
H201.90070.18050.82440.040*
C211.5450 (5)0.22091 (8)0.71255 (19)0.0296 (6)
H211.51870.23370.76970.036*
C220.8584 (5)0.34230 (9)0.71298 (17)0.0278 (5)
H22A1.03100.36390.74470.033*
H22B0.92960.30830.72760.033*
C230.7109 (5)0.35207 (8)0.77629 (18)0.0284 (6)
H23A0.55430.32770.75240.034*
H23B0.85690.34880.86110.034*
C240.5798 (5)0.40236 (8)0.74956 (17)0.0255 (5)
H24A0.73870.42670.77860.031*
H24B0.48190.40760.79070.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0244 (9)0.0315 (9)0.0193 (8)0.0037 (7)0.0062 (7)0.0010 (7)
C10.0206 (12)0.0252 (12)0.0255 (12)0.0021 (10)0.0100 (10)0.0048 (10)
C20.0177 (12)0.0262 (13)0.0251 (12)0.0036 (10)0.0075 (10)0.0033 (10)
C30.0238 (13)0.0232 (12)0.0217 (11)0.0001 (10)0.0096 (10)0.0011 (10)
C40.0194 (12)0.0209 (12)0.0218 (11)0.0016 (10)0.0102 (10)0.0006 (9)
C50.0181 (12)0.0195 (11)0.0234 (12)0.0030 (10)0.0099 (10)0.0007 (9)
C60.0171 (11)0.0206 (11)0.0224 (11)0.0001 (10)0.0096 (10)0.0037 (10)
C70.0210 (12)0.0244 (12)0.0219 (12)0.0009 (10)0.0088 (10)0.0005 (10)
C80.0269 (13)0.0280 (13)0.0209 (12)0.0022 (11)0.0128 (11)0.0000 (10)
C90.0289 (14)0.0266 (13)0.0231 (12)0.0027 (11)0.0150 (11)0.0004 (10)
C100.0232 (13)0.0238 (12)0.0271 (12)0.0023 (10)0.0145 (11)0.0001 (10)
C110.0214 (13)0.0322 (14)0.0284 (12)0.0025 (11)0.0112 (11)0.0039 (11)
C120.0272 (14)0.0322 (14)0.0474 (16)0.0024 (11)0.0219 (13)0.0068 (12)
C130.0507 (18)0.0389 (16)0.0488 (17)0.0095 (14)0.0377 (15)0.0128 (13)
C140.0494 (19)0.0605 (19)0.0235 (13)0.0034 (15)0.0162 (13)0.0085 (13)
C150.0321 (15)0.0457 (16)0.0291 (14)0.0074 (13)0.0115 (12)0.0024 (12)
C160.0231 (13)0.0202 (12)0.0270 (12)0.0003 (10)0.0144 (11)0.0002 (10)
C170.0299 (14)0.0298 (13)0.0272 (13)0.0013 (11)0.0164 (11)0.0022 (11)
C180.0398 (16)0.0328 (14)0.0409 (15)0.0021 (12)0.0285 (13)0.0080 (12)
C190.0284 (14)0.0247 (13)0.0535 (17)0.0047 (11)0.0241 (13)0.0001 (12)
C200.0346 (15)0.0272 (13)0.0317 (13)0.0056 (11)0.0144 (12)0.0045 (11)
C210.0395 (15)0.0239 (12)0.0271 (13)0.0015 (11)0.0197 (12)0.0000 (10)
C220.0219 (12)0.0377 (14)0.0193 (11)0.0063 (11)0.0088 (10)0.0052 (10)
C230.0259 (13)0.0347 (14)0.0206 (12)0.0023 (11)0.0107 (10)0.0026 (10)
C240.0226 (13)0.0298 (13)0.0198 (11)0.0033 (10)0.0093 (10)0.0026 (10)
Geometric parameters (Å, º) top
O1—C51.228 (2)C14—H140.9500
C1—C21.195 (3)C14—C151.383 (3)
C1—C101.432 (3)C15—H150.9500
C2—C31.417 (3)C16—C171.396 (3)
C3—H30.9500C16—C211.398 (3)
C3—C41.334 (3)C17—H170.9500
C4—C51.489 (3)C17—C181.379 (3)
C4—C241.510 (3)C18—H180.9500
C5—C61.479 (3)C18—C191.380 (3)
C6—C71.336 (3)C19—H190.9500
C6—C221.514 (3)C19—C201.379 (3)
C7—H70.9500C20—H200.9500
C7—C81.414 (3)C20—C211.370 (3)
C8—C91.196 (3)C21—H210.9500
C9—C161.425 (3)C22—H22A0.9900
C10—C111.387 (3)C22—H22B0.9900
C10—C151.390 (3)C22—C231.517 (3)
C11—H110.9500C23—H23A0.9900
C11—C121.373 (3)C23—H23B0.9900
C12—H120.9500C23—C241.508 (3)
C12—C131.372 (3)C24—H24A0.9900
C13—H130.9500C24—H24B0.9900
C13—C141.374 (4)
C2—C1—C10179.0 (3)C17—C16—C9121.1 (2)
C1—C2—C3177.7 (2)C17—C16—C21118.5 (2)
C2—C3—H3117.1C21—C16—C9120.5 (2)
C4—C3—C2125.8 (2)C16—C17—H17119.9
C4—C3—H3117.1C18—C17—C16120.3 (2)
C3—C4—C5117.1 (2)C18—C17—H17119.9
C3—C4—C24123.6 (2)C17—C18—H18119.7
C5—C4—C24119.21 (19)C17—C18—C19120.5 (2)
O1—C5—C4120.6 (2)C19—C18—H18119.7
O1—C5—C6120.7 (2)C18—C19—H19120.2
C6—C5—C4118.68 (19)C20—C19—C18119.6 (2)
C5—C6—C22119.67 (19)C20—C19—H19120.2
C7—C6—C5118.09 (19)C19—C20—H20119.7
C7—C6—C22122.2 (2)C21—C20—C19120.6 (2)
C6—C7—H7117.6C21—C20—H20119.7
C6—C7—C8124.9 (2)C16—C21—H21119.7
C8—C7—H7117.6C20—C21—C16120.6 (2)
C9—C8—C7178.5 (2)C20—C21—H21119.7
C8—C9—C16178.5 (2)C6—C22—H22A109.1
C11—C10—C1120.9 (2)C6—C22—H22B109.1
C11—C10—C15118.7 (2)C6—C22—C23112.64 (19)
C15—C10—C1120.4 (2)H22A—C22—H22B107.8
C10—C11—H11119.6C23—C22—H22A109.1
C12—C11—C10120.8 (2)C23—C22—H22B109.1
C12—C11—H11119.6C22—C23—H23A109.5
C11—C12—H12120.0C22—C23—H23B109.5
C13—C12—C11120.1 (2)H23A—C23—H23B108.0
C13—C12—H12120.0C24—C23—C22110.91 (19)
C12—C13—H13120.0C24—C23—H23A109.5
C12—C13—C14120.1 (2)C24—C23—H23B109.5
C14—C13—H13120.0C4—C24—H24A109.3
C13—C14—H14119.9C4—C24—H24B109.3
C13—C14—C15120.2 (2)C23—C24—C4111.74 (18)
C15—C14—H14119.9C23—C24—H24A109.3
C10—C15—H15120.0C23—C24—H24B109.3
C14—C15—C10120.1 (2)H24A—C24—H24B107.9
C14—C15—H15120.0
2,6-Bis[3-(4-bromophenyl)prop-2-yn-1-ylidene]cyclohexanone (3d) top
Crystal data top
C24H16Br2ODx = 1.589 Mg m3
Mr = 480.19Synchrotron radiation, λ = 0.9699 Å
Orthorhombic, Pca21Cell parameters from 3568 reflections
a = 12.006 (2) Åθ = 5.3–38.6°
b = 5.2243 (10) ŵ = 1.02 mm1
c = 31.998 (6) ÅT = 100 K
V = 2007.0 (7) Å3Needle, yellow
Z = 40.15 × 0.01 × 0.01 mm
F(000) = 952
Data collection top
Mar CCD
diffractometer
2569 reflections with I > 2σ(I)
phi–scanRint = 0.129
Absorption correction: multi-scan
(SCALA; Evans, 2006)
θmax = 38.4°, θmin = 4.6°
h = 1415
9749 measured reflectionsk = 66
3927 independent reflectionsl = 3839
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.079 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.258(Δ/σ)max = 0.012
S = 1.00Δρmax = 0.95 e Å3
3927 reflectionsΔρmin = 1.42 e Å3
244 parametersAbsolute structure: Flack x determined using 812 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.47 (7)
Primary atom site location: dual
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.94120 (15)1.6770 (3)0.72569 (5)0.0503 (5)
Br20.90419 (16)1.1722 (3)0.27438 (6)0.0516 (6)
O10.5159 (11)0.169 (2)0.5168 (4)0.069 (4)
C140.9401 (12)1.303 (3)0.6603 (6)0.046 (4)
H141.01711.34160.65810.056*
C150.8918 (13)1.123 (3)0.6339 (5)0.046 (3)
H150.93571.04000.61330.055*
C70.6106 (14)0.054 (3)0.4458 (5)0.055 (4)
H70.53190.04310.44850.066*
C170.6827 (14)0.661 (3)0.3295 (5)0.050 (4)
H170.60680.61440.32590.060*
C10.7256 (14)0.880 (3)0.6105 (5)0.051 (4)
C20.6796 (13)0.726 (3)0.5886 (5)0.050 (4)
C80.6544 (14)0.211 (3)0.4132 (5)0.050 (4)
C130.8740 (13)1.426 (3)0.6902 (4)0.044 (3)
C120.7614 (13)1.372 (3)0.6946 (5)0.046 (4)
H120.71681.45810.71470.055*
C160.7460 (13)0.544 (3)0.3607 (5)0.051 (4)
C90.6963 (15)0.357 (3)0.3885 (5)0.051 (4)
C200.9045 (16)0.802 (3)0.3399 (6)0.053 (4)
H200.97990.85320.34350.063*
C60.6735 (13)0.081 (3)0.4732 (6)0.050 (4)
C220.8056 (14)0.403 (3)0.5298 (5)0.051 (4)
H22A0.84050.27450.54840.061*
H22B0.83250.57420.53860.061*
C50.6153 (14)0.208 (3)0.5089 (6)0.054 (4)
C210.8582 (15)0.612 (3)0.3654 (5)0.051 (4)
H210.90280.52820.38580.061*
C100.7787 (13)1.064 (3)0.6377 (5)0.046 (3)
C40.6823 (13)0.392 (3)0.5350 (5)0.047 (3)
C30.6262 (15)0.546 (3)0.5621 (5)0.056 (4)
H30.54740.53220.56330.067*
C190.8392 (13)0.916 (3)0.3093 (5)0.051 (4)
C110.7173 (14)1.188 (3)0.6690 (6)0.057 (4)
H110.64131.14280.67250.068*
C180.7297 (14)0.847 (3)0.3036 (6)0.051 (4)
H180.68650.92530.28220.062*
C230.8424 (15)0.353 (3)0.4848 (6)0.057 (4)
H23A0.92470.35610.48310.068*
H23B0.81300.48930.46630.068*
C240.7985 (12)0.091 (3)0.4705 (5)0.049 (4)
H24A0.82200.05880.44130.059*
H24B0.83070.04540.48830.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0521 (10)0.0486 (10)0.0502 (10)0.0017 (7)0.0008 (9)0.0040 (11)
Br20.0530 (10)0.0492 (10)0.0526 (11)0.0004 (7)0.0008 (9)0.0026 (11)
O10.040 (7)0.086 (9)0.082 (9)0.001 (5)0.010 (6)0.033 (6)
C140.033 (8)0.046 (9)0.060 (11)0.005 (6)0.001 (7)0.001 (7)
C150.050 (9)0.051 (8)0.037 (8)0.004 (6)0.001 (7)0.006 (7)
C70.054 (9)0.054 (10)0.056 (9)0.006 (7)0.009 (7)0.011 (8)
C170.048 (9)0.056 (9)0.046 (9)0.000 (7)0.001 (7)0.007 (7)
C10.061 (10)0.049 (8)0.042 (8)0.005 (7)0.004 (7)0.001 (7)
C20.045 (9)0.048 (8)0.057 (11)0.001 (7)0.000 (7)0.016 (8)
C80.046 (9)0.058 (9)0.046 (9)0.006 (7)0.003 (7)0.004 (8)
C130.053 (8)0.038 (7)0.043 (8)0.005 (7)0.002 (6)0.009 (7)
C120.049 (9)0.049 (8)0.040 (8)0.008 (7)0.004 (6)0.010 (7)
C160.044 (8)0.056 (10)0.052 (9)0.000 (7)0.000 (7)0.001 (8)
C90.053 (10)0.053 (9)0.048 (9)0.001 (7)0.001 (7)0.004 (7)
C200.056 (11)0.050 (10)0.052 (11)0.001 (7)0.003 (8)0.009 (8)
C60.044 (8)0.044 (8)0.063 (10)0.001 (7)0.004 (7)0.011 (8)
C220.053 (9)0.047 (8)0.053 (9)0.009 (7)0.008 (7)0.004 (8)
C50.040 (10)0.047 (9)0.075 (13)0.003 (6)0.004 (8)0.012 (8)
C210.062 (10)0.042 (8)0.048 (9)0.003 (7)0.004 (8)0.004 (7)
C100.059 (9)0.036 (7)0.042 (8)0.003 (7)0.007 (7)0.000 (7)
C40.043 (8)0.046 (8)0.050 (9)0.004 (6)0.008 (6)0.005 (7)
C30.050 (9)0.055 (9)0.063 (10)0.004 (7)0.006 (8)0.016 (8)
C190.052 (9)0.053 (8)0.048 (9)0.012 (7)0.004 (7)0.004 (8)
C110.043 (9)0.061 (10)0.066 (11)0.005 (7)0.013 (8)0.014 (8)
C180.044 (9)0.051 (9)0.059 (10)0.004 (6)0.011 (8)0.007 (8)
C230.048 (9)0.066 (10)0.056 (10)0.002 (7)0.004 (8)0.009 (8)
C240.046 (8)0.045 (8)0.057 (10)0.004 (7)0.008 (7)0.012 (8)
Geometric parameters (Å, º) top
Br1—C131.913 (16)C20—H200.9500
Br2—C191.912 (16)C20—C211.40 (2)
O1—C51.24 (2)C20—C191.39 (2)
C14—H140.9500C6—C51.49 (2)
C14—C151.39 (2)C6—C241.50 (2)
C14—C131.40 (2)C22—H22A0.9900
C15—H150.9500C22—H22B0.9900
C15—C101.40 (2)C22—C41.49 (2)
C7—H70.9500C22—C231.53 (2)
C7—C81.43 (2)C5—C41.51 (2)
C7—C61.36 (2)C21—H210.9500
C17—H170.9500C10—C111.40 (2)
C17—C161.40 (2)C4—C31.36 (2)
C17—C181.40 (2)C3—H30.9500
C1—C21.20 (2)C19—C181.37 (2)
C1—C101.45 (2)C11—H110.9500
C2—C31.42 (2)C18—H180.9500
C8—C91.21 (2)C23—H23A0.9900
C13—C121.39 (2)C23—H23B0.9900
C12—H120.9500C23—C241.54 (2)
C12—C111.37 (2)C24—H24A0.9900
C16—C91.45 (2)C24—H24B0.9900
C16—C211.40 (2)
C15—C14—H14120.3O1—C5—C6122.3 (15)
C15—C14—C13119.3 (14)O1—C5—C4120.5 (15)
C13—C14—H14120.3C6—C5—C4117.2 (14)
C14—C15—H15119.9C16—C21—C20119.8 (16)
C14—C15—C10120.1 (14)C16—C21—H21120.1
C10—C15—H15119.9C20—C21—H21120.1
C8—C7—H7117.7C15—C10—C1121.6 (13)
C6—C7—H7117.7C15—C10—C11118.1 (14)
C6—C7—C8124.6 (15)C11—C10—C1120.3 (14)
C16—C17—H17119.7C22—C4—C5119.6 (14)
C16—C17—C18120.6 (16)C3—C4—C22122.7 (15)
C18—C17—H17119.7C3—C4—C5117.8 (14)
C2—C1—C10178.6 (18)C2—C3—H3118.4
C1—C2—C3179.0 (19)C4—C3—C2123.3 (16)
C9—C8—C7173.8 (17)C4—C3—H3118.4
C14—C13—Br1118.9 (11)C20—C19—Br2118.8 (13)
C12—C13—Br1119.4 (11)C18—C19—Br2119.7 (12)
C12—C13—C14121.8 (14)C18—C19—C20121.6 (15)
C13—C12—H12121.3C12—C11—C10123.2 (15)
C11—C12—C13117.4 (14)C12—C11—H11118.4
C11—C12—H12121.3C10—C11—H11118.4
C17—C16—C9120.7 (15)C17—C18—H18120.4
C17—C16—C21119.4 (15)C19—C18—C17119.3 (16)
C21—C16—C9119.9 (15)C19—C18—H18120.4
C8—C9—C16176.8 (17)C22—C23—H23A109.8
C21—C20—H20120.3C22—C23—H23B109.8
C19—C20—H20120.3C22—C23—C24109.5 (14)
C19—C20—C21119.3 (16)H23A—C23—H23B108.2
C7—C6—C5117.7 (14)C24—C23—H23A109.8
C7—C6—C24122.3 (14)C24—C23—H23B109.8
C5—C6—C24119.8 (14)C6—C24—C23110.7 (14)
H22A—C22—H22B107.8C6—C24—H24A109.5
C4—C22—H22A109.1C6—C24—H24B109.5
C4—C22—H22B109.1C23—C24—H24A109.5
C4—C22—C23112.6 (14)C23—C24—H24B109.5
C23—C22—H22A109.1H24A—C24—H24B108.1
C23—C22—H22B109.1
4-tert-Butyl-2,6-bis(3-phenylprop-2-yn-1-ylidene)cyclohexanone (3e) top
Crystal data top
C28H25OF(000) = 804
Mr = 377.48Dx = 1.136 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.9422 (14) ÅCell parameters from 3825 reflections
b = 6.9614 (7) Åθ = 2.8–30.5°
c = 24.721 (3) ŵ = 0.07 mm1
β = 97.732 (2)°T = 120 K
V = 2207.0 (4) Å3Needle, yellow
Z = 40.48 × 0.01 × 0.01 mm
Data collection top
Bruker SMART APEX CCD area detector
diffractometer
6739 independent reflections
Radiation source: sealed tube2902 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.165
Detector resolution: 8 pixels mm-1θmax = 30.6°, θmin = 1.7°
ω and φ scansh = 1818
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 = 99
Tmin = 0.443, Tmax = 0.746l = 3535
36697 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.078H-atom parameters constrained
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.050P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
6739 reflectionsΔρmax = 0.41 e Å3
304 parametersΔρmin = 0.17 e Å3
36 restraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.37750 (10)0.2693 (2)0.47019 (5)0.0430 (4)
C10.55701 (14)0.2194 (3)0.67830 (8)0.0338 (4)
C20.52205 (14)0.2311 (3)0.63087 (8)0.0367 (5)
C30.47789 (15)0.2434 (3)0.57535 (7)0.0389 (5)
H30.40410.25250.56760.047*
C40.53249 (14)0.2433 (3)0.53268 (7)0.0333 (4)
C50.47354 (14)0.2606 (3)0.47740 (7)0.0336 (4)
C60.53363 (14)0.2657 (3)0.43039 (7)0.0415 (5)
C70.48361 (14)0.2570 (3)0.38011 (7)0.0331 (4)
H70.40960.25110.37610.040*
C80.53114 (14)0.2557 (3)0.33169 (7)0.0335 (4)
C90.57153 (14)0.2512 (2)0.29079 (7)0.0323 (4)
C100.59790 (14)0.2086 (2)0.73488 (7)0.0313 (4)
C110.55096 (15)0.3125 (3)0.77338 (8)0.0384 (5)
H110.49080.38790.76190.046*
C120.59114 (16)0.3064 (3)0.82770 (8)0.0438 (5)
H120.55890.37810.85350.053*
C130.67802 (16)0.1966 (3)0.84486 (8)0.0440 (5)
H130.70630.19410.88240.053*
C140.72383 (15)0.0905 (3)0.80746 (8)0.0455 (5)
H140.78270.01240.81950.055*
C150.68492 (14)0.0967 (3)0.75281 (8)0.0390 (5)
H150.71760.02440.72730.047*
C160.64889 (14)0.2301 (3)0.54116 (8)0.0479 (5)
H16A0.67650.34350.56250.057*
H16B0.66890.11500.56360.057*
C170.70079 (15)0.2195 (4)0.49164 (8)0.0528 (6)
C190.61877 (14)0.2410 (2)0.24173 (7)0.0307 (4)
C200.56410 (15)0.1614 (3)0.19490 (8)0.0438 (5)
H200.49460.11780.19510.053*
C210.61104 (18)0.1457 (3)0.14801 (8)0.0574 (6)
H210.57390.08930.11620.069*
C220.71109 (18)0.2112 (3)0.14710 (9)0.0540 (6)
H220.74250.20140.11460.065*
C230.76561 (16)0.2908 (3)0.19325 (9)0.0480 (5)
H230.83470.33600.19250.058*
C240.72047 (15)0.3053 (3)0.24064 (8)0.0390 (5)
H240.75880.35910.27250.047*
C250.82077 (14)0.2134 (3)0.50075 (8)0.0430 (5)
C180.6479 (2)0.3162 (6)0.44357 (11)0.0436 (7)0.7
H18A0.68360.28300.41180.052*0.7
H18B0.65430.45670.44920.052*0.7
C260.8553 (3)0.4235 (6)0.50859 (15)0.0593 (11)0.6
H26A0.83130.49640.47530.089*0.6
H26B0.93150.42950.51610.089*0.6
H26C0.82510.47890.53940.089*0.6
C270.8630 (3)0.1323 (8)0.44951 (16)0.0693 (12)0.6
H27A0.83920.00050.44330.104*0.6
H27B0.93940.13530.45530.104*0.6
H27C0.83710.21080.41760.104*0.6
C280.8626 (3)0.0952 (7)0.55006 (16)0.0625 (11)0.6
H28A0.84080.15290.58290.094*0.6
H28B0.93890.09190.55370.094*0.6
H28C0.83520.03590.54570.094*0.6
C18A0.6494 (4)0.1728 (10)0.4419 (2)0.0265 (13)0.3
H18C0.64360.03120.43920.032*0.3
H18D0.69070.21730.41340.032*0.3
C26A0.8747 (5)0.2903 (12)0.5563 (3)0.079 (2)0.4
H26D0.86610.43000.55760.118*0.4
H26E0.94920.25890.56030.118*0.4
H26F0.84310.23070.58600.118*0.4
C27A0.8751 (5)0.3016 (11)0.4568 (3)0.0715 (19)0.4
H27D0.84640.24770.42130.107*0.4
H27E0.94990.27380.46410.107*0.4
H27F0.86430.44100.45640.107*0.4
C28A0.8410 (4)0.0044 (8)0.5024 (3)0.0574 (15)0.4
H28D0.79990.06470.52820.086*0.4
H28E0.91530.02850.51400.086*0.4
H28F0.82080.05870.46590.086*0.4
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0313 (7)0.0606 (9)0.0387 (8)0.0078 (7)0.0106 (6)0.0009 (6)
C10.0375 (10)0.0309 (10)0.0363 (12)0.0036 (8)0.0175 (9)0.0015 (8)
C20.0390 (11)0.0410 (12)0.0333 (11)0.0039 (9)0.0169 (9)0.0004 (9)
C30.0368 (10)0.0483 (12)0.0339 (11)0.0001 (10)0.0128 (8)0.0012 (9)
C40.0351 (10)0.0367 (11)0.0298 (10)0.0002 (9)0.0105 (8)0.0003 (8)
C50.0328 (10)0.0371 (11)0.0324 (10)0.0048 (9)0.0105 (8)0.0018 (8)
C60.0318 (10)0.0633 (14)0.0310 (11)0.0050 (10)0.0104 (8)0.0051 (9)
C70.0325 (10)0.0338 (11)0.0332 (10)0.0071 (8)0.0058 (8)0.0024 (8)
C80.0359 (10)0.0330 (11)0.0307 (10)0.0061 (9)0.0015 (8)0.0024 (8)
C90.0362 (10)0.0276 (10)0.0326 (10)0.0031 (8)0.0030 (8)0.0030 (8)
C100.0350 (10)0.0284 (10)0.0322 (10)0.0047 (8)0.0111 (8)0.0019 (8)
C110.0417 (11)0.0366 (11)0.0379 (11)0.0064 (9)0.0094 (9)0.0001 (9)
C120.0525 (13)0.0466 (13)0.0346 (11)0.0046 (10)0.0143 (10)0.0074 (9)
C130.0482 (12)0.0477 (13)0.0351 (11)0.0008 (11)0.0020 (9)0.0023 (9)
C140.0405 (12)0.0426 (12)0.0519 (14)0.0065 (10)0.0004 (10)0.0048 (10)
C150.0381 (11)0.0405 (12)0.0402 (12)0.0016 (9)0.0119 (9)0.0102 (9)
C160.0331 (11)0.0770 (16)0.0345 (11)0.0006 (11)0.0081 (8)0.0043 (10)
C170.0287 (10)0.1027 (19)0.0285 (11)0.0149 (11)0.0098 (8)0.0147 (11)
C190.0351 (10)0.0275 (10)0.0305 (10)0.0041 (8)0.0082 (8)0.0030 (8)
C200.0388 (11)0.0545 (13)0.0385 (12)0.0057 (10)0.0063 (9)0.0026 (9)
C210.0602 (15)0.0797 (18)0.0334 (12)0.0090 (13)0.0102 (10)0.0126 (11)
C220.0618 (15)0.0611 (15)0.0439 (13)0.0021 (12)0.0250 (11)0.0062 (11)
C230.0452 (12)0.0433 (13)0.0597 (14)0.0051 (10)0.0229 (11)0.0006 (10)
C240.0422 (12)0.0336 (11)0.0414 (12)0.0029 (9)0.0069 (9)0.0044 (8)
C250.0300 (10)0.0619 (14)0.0385 (11)0.0029 (10)0.0093 (8)0.0091 (10)
C180.0341 (17)0.063 (2)0.0356 (17)0.0014 (17)0.0129 (13)0.0104 (16)
C260.0322 (19)0.089 (3)0.057 (2)0.0208 (19)0.0070 (17)0.016 (2)
C270.042 (2)0.103 (3)0.068 (3)0.025 (2)0.0232 (19)0.004 (3)
C280.035 (2)0.090 (3)0.062 (3)0.017 (2)0.0027 (18)0.031 (2)
C18A0.019 (3)0.027 (3)0.035 (4)0.002 (3)0.013 (3)0.009 (3)
C26A0.049 (3)0.105 (5)0.080 (4)0.008 (4)0.000 (3)0.025 (4)
C27A0.041 (3)0.084 (4)0.093 (4)0.004 (3)0.021 (3)0.023 (4)
C28A0.033 (3)0.062 (4)0.077 (4)0.009 (3)0.012 (3)0.004 (3)
Geometric parameters (Å, º) top
O1—C51.233 (2)C20—C211.384 (3)
C1—C21.201 (2)C21—H210.9500
C1—C101.430 (3)C21—C221.376 (3)
C2—C31.416 (3)C22—H220.9500
C3—H30.9500C22—C231.375 (3)
C3—C41.346 (2)C23—H230.9500
C4—C51.478 (2)C23—C241.381 (3)
C4—C161.496 (2)C24—H240.9500
C5—C61.483 (2)C25—C261.534 (4)
C6—C71.323 (2)C25—C271.552 (4)
C6—C181.513 (3)C25—C281.509 (4)
C6—C18A1.622 (6)C25—C26A1.549 (6)
C7—H70.9500C25—C27A1.502 (6)
C7—C81.417 (2)C25—C28A1.538 (6)
C8—C91.200 (2)C18—H18A0.9900
C9—C191.431 (2)C18—H18B0.9900
C10—C111.398 (2)C26—H26A0.9800
C10—C151.392 (3)C26—H26B0.9800
C11—H110.9500C26—H26C0.9800
C11—C121.374 (3)C27—H27A0.9800
C12—H120.9500C27—H27B0.9800
C12—C131.378 (3)C27—H27C0.9800
C13—H130.9500C28—H28A0.9800
C13—C141.378 (3)C28—H28B0.9800
C14—H140.9500C28—H28C0.9800
C14—C151.378 (3)C18A—H18C0.9900
C15—H150.9500C18A—H18D0.9900
C16—H16A0.9900C26A—H26D0.9800
C16—H16B0.9900C26A—H26E0.9800
C16—C171.475 (2)C26A—H26F0.9800
C17—C251.539 (3)C27A—H27D0.9800
C17—C181.455 (3)C27A—H27E0.9800
C17—C18A1.355 (6)C27A—H27F0.9800
C19—C201.388 (3)C28A—H28D0.9800
C19—C241.394 (3)C28A—H28E0.9800
C20—H200.9500C28A—H28F0.9800
C2—C1—C10179.1 (2)C24—C23—H23119.8
C1—C2—C3178.31 (19)C19—C24—H24120.0
C2—C3—H3117.5C23—C24—C19120.07 (18)
C4—C3—C2124.98 (17)C23—C24—H24120.0
C4—C3—H3117.5C17—C25—C27110.5 (2)
C3—C4—C5117.67 (16)C17—C25—C26A116.5 (3)
C3—C4—C16121.00 (16)C26—C25—C17105.3 (2)
C5—C4—C16121.31 (15)C26—C25—C27108.7 (3)
O1—C5—C4121.52 (15)C28—C25—C17112.2 (2)
O1—C5—C6120.67 (16)C28—C25—C26110.6 (3)
C4—C5—C6117.81 (15)C28—C25—C27109.5 (3)
C5—C6—C18115.94 (18)C27A—C25—C17116.3 (3)
C5—C6—C18A115.0 (2)C27A—C25—C26A107.5 (4)
C7—C6—C5119.54 (17)C27A—C25—C28A109.1 (4)
C7—C6—C18123.61 (18)C28A—C25—C17101.3 (3)
C7—C6—C18A118.1 (2)C28A—C25—C26A105.2 (4)
C6—C7—H7117.3C6—C18—H18A108.7
C6—C7—C8125.48 (17)C6—C18—H18B108.7
C8—C7—H7117.3C17—C18—C6114.0 (2)
C9—C8—C7178.87 (19)C17—C18—H18A108.7
C8—C9—C19178.5 (2)C17—C18—H18B108.7
C11—C10—C1120.08 (17)H18A—C18—H18B107.6
C15—C10—C1121.23 (16)C25—C26—H26A109.5
C15—C10—C11118.69 (16)C25—C26—H26B109.5
C10—C11—H11119.7C25—C26—H26C109.5
C12—C11—C10120.50 (18)H26A—C26—H26B109.5
C12—C11—H11119.7H26A—C26—H26C109.5
C11—C12—H12119.9H26B—C26—H26C109.5
C11—C12—C13120.23 (18)C25—C27—H27A109.5
C13—C12—H12119.9C25—C27—H27B109.5
C12—C13—H13120.1C25—C27—H27C109.5
C14—C13—C12119.85 (19)H27A—C27—H27B109.5
C14—C13—H13120.1H27A—C27—H27C109.5
C13—C14—H14119.8H27B—C27—H27C109.5
C15—C14—C13120.49 (19)C25—C28—H28A109.5
C15—C14—H14119.8C25—C28—H28B109.5
C10—C15—H15119.9C25—C28—H28C109.5
C14—C15—C10120.22 (17)H28A—C28—H28B109.5
C14—C15—H15119.9H28A—C28—H28C109.5
C4—C16—H16A108.1H28B—C28—H28C109.5
C4—C16—H16B108.1C6—C18A—H18C109.0
H16A—C16—H16B107.3C6—C18A—H18D109.0
C17—C16—C4116.69 (16)C17—C18A—C6113.1 (4)
C17—C16—H16A108.1C17—C18A—H18C109.0
C17—C16—H16B108.1C17—C18A—H18D109.0
C16—C17—C25116.29 (16)H18C—C18A—H18D107.8
C18—C17—C16115.98 (19)C25—C26A—H26D109.5
C18—C17—C25119.12 (18)C25—C26A—H26E109.5
C18A—C17—C16122.8 (3)C25—C26A—H26F109.5
C18A—C17—C25119.2 (3)H26D—C26A—H26E109.5
C20—C19—C9119.90 (17)H26D—C26A—H26F109.5
C20—C19—C24119.25 (16)H26E—C26A—H26F109.5
C24—C19—C9120.82 (16)C25—C27A—H27D109.5
C19—C20—H20120.1C25—C27A—H27E109.5
C21—C20—C19119.88 (19)C25—C27A—H27F109.5
C21—C20—H20120.1H27D—C27A—H27E109.5
C20—C21—H21119.7H27D—C27A—H27F109.5
C22—C21—C20120.5 (2)H27E—C27A—H27F109.5
C22—C21—H21119.7C25—C28A—H28D109.5
C21—C22—H22120.0C25—C28A—H28E109.5
C23—C22—C21119.93 (19)C25—C28A—H28F109.5
C23—C22—H22120.0H28D—C28A—H28E109.5
C22—C23—H23119.8H28D—C28A—H28F109.5
C22—C23—C24120.33 (19)H28E—C28A—H28F109.5
O1—C5—C6—C77.9 (3)C16—C17—C25—C27160.2 (3)
O1—C5—C6—C18161.6 (2)C16—C17—C25—C2837.7 (3)
O1—C5—C6—C18A157.3 (3)C16—C17—C25—C26A21.1 (5)
C1—C10—C11—C12178.50 (17)C16—C17—C25—C27A149.5 (4)
C1—C10—C15—C14179.11 (18)C16—C17—C25—C28A92.4 (3)
C2—C3—C4—C5178.96 (17)C16—C17—C18—C649.9 (4)
C2—C3—C4—C160.2 (3)C16—C17—C18A—C639.1 (6)
C3—C4—C5—O12.1 (3)C19—C20—C21—C221.0 (3)
C3—C4—C5—C6178.41 (18)C20—C19—C24—C230.5 (3)
C3—C4—C16—C17176.5 (2)C20—C21—C22—C230.8 (4)
C4—C5—C6—C7171.65 (17)C21—C22—C23—C240.1 (3)
C4—C5—C6—C1818.9 (3)C22—C23—C24—C190.7 (3)
C4—C5—C6—C18A22.2 (3)C24—C19—C20—C210.4 (3)
C4—C16—C17—C25177.85 (19)C25—C17—C18—C6163.5 (2)
C4—C16—C17—C1830.2 (3)C25—C17—C18A—C6156.3 (3)
C4—C16—C17—C18A17.1 (5)C18—C6—C7—C813.0 (3)
C5—C4—C16—C174.8 (3)C18—C6—C18A—C1759.2 (4)
C5—C6—C7—C8178.37 (17)C18—C17—C25—C2664.0 (3)
C5—C6—C18—C1744.0 (3)C18—C17—C25—C2753.2 (4)
C5—C6—C18A—C1741.4 (5)C18—C17—C25—C28175.7 (3)
C7—C6—C18—C17147.0 (2)C18—C17—C25—C26A125.4 (4)
C7—C6—C18A—C17168.7 (3)C18—C17—C25—C27A3.0 (5)
C9—C19—C20—C21177.85 (19)C18—C17—C25—C28A121.1 (3)
C9—C19—C24—C23178.68 (17)C18—C17—C18A—C654.2 (4)
C10—C11—C12—C130.4 (3)C18A—C6—C7—C829.9 (4)
C11—C10—C15—C140.4 (3)C18A—C6—C18—C1753.7 (4)
C11—C12—C13—C140.9 (3)C18A—C17—C25—C26111.9 (4)
C12—C13—C14—C151.5 (3)C18A—C17—C25—C275.4 (5)
C13—C14—C15—C100.9 (3)C18A—C17—C25—C28127.8 (4)
C15—C10—C11—C121.0 (3)C18A—C17—C25—C26A173.3 (5)
C16—C4—C5—O1179.17 (18)C18A—C17—C25—C27A44.9 (6)
C16—C4—C5—C60.3 (3)C18A—C17—C25—C28A73.2 (5)
C16—C17—C25—C2682.6 (3)C18A—C17—C18—C661.1 (4)
4-tert-Butyl-2,6-bis[3-(4-methylphenyl)prop-2-yn-1-ylidene]cyclohexanone (3f) top
Crystal data top
C30H30OF(000) = 872
Mr = 406.54Dx = 1.090 Mg m3
Monoclinic, CcSynchrotron radiation, λ = 0.96990 Å
a = 6.4010 (13) ÅCell parameters from 3567 reflections
b = 21.350 (4) Åθ = 3.1–38.7°
c = 18.190 (4) ŵ = 0.14 mm1
β = 94.83 (3)°T = 120 K
V = 2477.1 (9) Å3Needle, yellow
Z = 40.5 × 0.02 × 0.02 mm
Data collection top
Mar CCD
diffractometer
2588 independent reflections
Radiation source: fine-focus sealed tube1287 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.238
phi–scanθmax = 38.4°, θmin = 2.6°
Absorption correction: multi-scan
(SCALA; Evans, 2006)
h = 78
Tmin = 0.899, Tmax = 0.902k = 2625
10989 measured reflectionsl = 2122
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.140H-atom parameters constrained
wR(F2) = 0.339 w = 1/[σ2(Fo2) + (0.010P)2 + 3.2P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
2588 reflectionsΔρmax = 0.37 e Å3
279 parametersΔρmin = 0.32 e Å3
23 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.146 (19)
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.

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.6468 (12)0.5022 (3)0.3726 (4)0.0721 (19)
C201.2839 (15)0.7564 (4)0.3294 (5)0.057 (2)
C30.8961 (16)0.6089 (5)0.3589 (5)0.066 (3)
H30.89490.57660.32290.079*
C11.1471 (16)0.7050 (5)0.3427 (5)0.063 (3)
C160.5004 (15)0.4357 (4)0.6742 (5)0.058 (2)
C50.6225 (14)0.5465 (4)0.4149 (4)0.058 (2)
C70.4256 (16)0.6031 (4)0.5156 (5)0.064 (3)
H7AA0.47900.59110.56630.076*0.50
H7AB0.27400.61200.51630.076*0.50
H7BC0.28640.62180.50160.076*0.50
H7BD0.42190.58660.56640.076*0.50
C21.0343 (15)0.6607 (5)0.3528 (5)0.059 (2)
C130.1701 (14)0.4651 (4)0.5893 (5)0.056 (2)
C140.2113 (16)0.5039 (4)0.6478 (5)0.061 (2)
H140.12800.54010.65870.073*
C251.4813 (15)0.7444 (4)0.2978 (5)0.059 (3)
H251.51840.70290.28530.071*
C60.4518 (15)0.5487 (4)0.4658 (4)0.054 (2)
C180.2899 (17)0.4120 (4)0.5732 (6)0.070 (3)
H180.25940.38540.53370.084*
C150.3830 (16)0.4886 (4)0.6922 (5)0.062 (3)
H150.41350.51440.73250.074*
C40.7618 (15)0.6034 (4)0.4157 (5)0.059 (2)
C120.0043 (17)0.4797 (4)0.5464 (6)0.066 (3)
C100.3228 (17)0.4973 (5)0.4630 (5)0.070 (3)
H100.35110.46480.42950.084*
C170.4578 (18)0.3979 (5)0.6160 (6)0.069 (3)
H170.54210.36200.60460.083*
C241.6161 (17)0.7943 (4)0.2859 (6)0.070 (3)
H241.74900.78590.26840.084*
C110.1459 (18)0.4886 (4)0.5073 (6)0.066 (3)
C211.237 (2)0.8178 (5)0.3458 (6)0.075 (3)
H211.10890.82670.36680.090*
C221.372 (2)0.8671 (5)0.3321 (7)0.088 (4)
H221.33740.90870.34500.105*
C270.5296 (17)0.7143 (5)0.5598 (6)0.078 (3)
C190.6853 (16)0.4200 (5)0.7179 (7)0.076 (3)
H19A0.64200.42250.77080.114*
H19B0.73430.37750.70560.114*
H19C0.79900.44990.70550.114*
C231.560 (2)0.8549 (4)0.2990 (7)0.086 (4)
C80.541 (3)0.6655 (7)0.4940 (12)0.061 (4)*0.50
H80.47660.68310.44640.073*0.50
C261.708 (2)0.9096 (5)0.2783 (7)0.093 (4)
H26A1.84640.90430.30510.139*
H26B1.64810.94980.29180.139*
H26C1.72240.90890.22510.139*
C90.767 (3)0.6405 (9)0.4860 (12)0.067 (4)*0.50
H9A0.86590.67590.48430.081*0.50
H9B0.81300.61360.52860.081*0.50
C290.316 (4)0.7380 (11)0.5528 (15)0.078 (4)*0.50
H29A0.26720.74150.50050.118*0.50
H29B0.31240.77930.57610.118*0.50
H29C0.22500.70910.57710.118*0.50
C280.642 (6)0.7750 (16)0.530 (2)0.098 (5)*0.50
H28A0.79250.77300.54400.147*0.50
H28B0.58290.81270.55070.147*0.50
H28C0.61810.77650.47570.147*0.50
C300.606 (5)0.6894 (13)0.6385 (16)0.099 (6)*0.50
H30A0.59910.72330.67450.148*0.50
H30B0.75080.67460.63860.148*0.50
H30C0.51560.65480.65160.148*0.50
C9A0.728 (4)0.6644 (10)0.4619 (13)0.067 (4)*0.50
H9AA0.86360.67830.48650.081*0.50
H9AB0.67320.69830.42840.081*0.50
C8A0.578 (3)0.6530 (8)0.5182 (11)0.061 (4)*0.50
H8A0.68030.63470.55700.073*0.50
C30A0.677 (3)0.7102 (12)0.6269 (12)0.099 (6)*0.50
H30D0.69790.66620.64090.148*0.50
H30E0.61930.73300.66730.148*0.50
H30F0.81200.72870.61690.148*0.50
C29A0.299 (2)0.7231 (11)0.5767 (13)0.078 (4)*0.50
H29D0.20960.72490.53030.118*0.50
H29E0.28540.76210.60410.118*0.50
H29F0.25630.68770.60630.118*0.50
C28A0.589 (4)0.7761 (13)0.5185 (16)0.098 (5)*0.50
H28D0.72540.77080.49890.147*0.50
H28E0.59490.81130.55320.147*0.50
H28F0.48190.78450.47780.147*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.089 (5)0.071 (4)0.059 (4)0.012 (3)0.023 (3)0.013 (3)
C200.065 (6)0.058 (5)0.045 (5)0.012 (5)0.011 (5)0.011 (4)
C30.075 (7)0.078 (6)0.044 (5)0.011 (5)0.005 (5)0.004 (4)
C10.067 (7)0.077 (6)0.040 (5)0.025 (6)0.016 (5)0.002 (4)
C160.063 (6)0.056 (4)0.054 (5)0.002 (5)0.002 (4)0.009 (4)
C50.064 (6)0.072 (6)0.039 (4)0.008 (5)0.008 (4)0.011 (4)
C70.081 (7)0.057 (5)0.052 (5)0.002 (5)0.002 (5)0.001 (4)
C20.059 (6)0.070 (6)0.046 (5)0.018 (5)0.003 (4)0.003 (4)
C130.060 (6)0.057 (4)0.050 (5)0.003 (4)0.003 (4)0.008 (4)
C140.067 (6)0.061 (5)0.053 (5)0.003 (5)0.002 (5)0.001 (4)
C250.074 (7)0.057 (5)0.043 (5)0.000 (5)0.018 (5)0.000 (4)
C60.068 (6)0.055 (5)0.039 (4)0.021 (4)0.011 (4)0.000 (3)
C180.080 (7)0.048 (5)0.082 (7)0.011 (5)0.007 (6)0.000 (4)
C150.075 (7)0.051 (5)0.060 (5)0.009 (4)0.009 (5)0.012 (4)
C40.065 (6)0.063 (5)0.051 (5)0.014 (5)0.009 (5)0.003 (4)
C120.067 (7)0.066 (6)0.065 (6)0.000 (5)0.004 (6)0.009 (5)
C100.085 (8)0.074 (6)0.049 (5)0.002 (6)0.002 (5)0.003 (4)
C170.079 (7)0.060 (5)0.066 (6)0.001 (5)0.006 (5)0.001 (5)
C240.065 (7)0.057 (5)0.085 (7)0.009 (5)0.007 (5)0.002 (5)
C110.074 (7)0.068 (6)0.055 (6)0.001 (5)0.006 (6)0.006 (5)
C210.102 (8)0.060 (5)0.060 (6)0.028 (6)0.015 (6)0.006 (4)
C220.111 (10)0.060 (6)0.086 (8)0.031 (7)0.033 (8)0.024 (5)
C270.072 (5)0.092 (5)0.072 (5)0.019 (4)0.014 (4)0.021 (4)
C190.060 (6)0.079 (6)0.088 (7)0.002 (5)0.005 (5)0.038 (6)
C230.111 (10)0.044 (5)0.091 (8)0.008 (6)0.056 (8)0.004 (5)
C260.091 (6)0.083 (5)0.101 (6)0.009 (5)0.012 (5)0.005 (5)
Geometric parameters (Å, º) top
O1—C51.238 (10)C22—C231.416 (19)
C20—C11.439 (15)C27—C81.59 (2)
C20—C251.454 (14)C27—C291.45 (3)
C20—C211.383 (12)C27—C281.60 (3)
C3—H30.9500C27—C301.57 (3)
C3—C21.426 (16)C27—C8A1.56 (2)
C3—C41.402 (13)C27—C30A1.482 (16)
C1—C21.213 (14)C27—C29A1.543 (16)
C16—C151.380 (13)C27—C28A1.579 (17)
C16—C171.377 (14)C19—H19A0.9800
C16—C191.517 (14)C19—H19B0.9800
C5—C61.491 (12)C19—H19C0.9800
C5—C41.505 (13)C23—C261.569 (17)
C7—H7AA0.9900C8—H81.0000
C7—H7AB0.9900C8—C91.559 (18)
C7—H7BC0.9900C26—H26A0.9800
C7—H7BD0.9900C26—H26B0.9800
C7—C61.491 (11)C26—H26C0.9800
C7—C81.589 (15)C9—H9A0.9900
C7—C8A1.446 (15)C9—H9B0.9900
C13—C141.390 (13)C29—H29A0.9800
C13—C181.387 (12)C29—H29B0.9800
C13—C121.449 (14)C29—H29C0.9800
C14—H140.9500C28—H28A0.9800
C14—C151.454 (14)C28—H28B0.9800
C25—H250.9500C28—H28C0.9800
C25—C241.399 (13)C30—H30A0.9800
C6—C101.373 (13)C30—H30B0.9800
C18—H180.9500C30—H30C0.9800
C18—C171.412 (15)C9A—H9AA0.9900
C15—H150.9500C9A—H9AB0.9900
C4—C91.50 (2)C9A—C8A1.48 (3)
C4—C9A1.58 (2)C8A—H8A1.0000
C12—C111.213 (15)C30A—H30D0.9800
C10—H100.9500C30A—H30E0.9800
C10—C111.457 (16)C30A—H30F0.9800
C17—H170.9500C29A—H29D0.9800
C24—H240.9500C29A—H29E0.9800
C24—C231.370 (14)C29A—H29F0.9800
C21—H210.9500C28A—H28D0.9800
C21—C221.398 (19)C28A—H28E0.9800
C22—H220.9500C28A—H28F0.9800
C1—C20—C25119.5 (7)C30—C27—C28118.3 (19)
C21—C20—C1122.7 (10)C30—C27—C28A130.5 (17)
C21—C20—C25117.8 (10)C8A—C27—C820.1 (10)
C2—C3—H3118.5C8A—C27—C28113.6 (16)
C4—C3—H3118.5C8A—C27—C3095.7 (14)
C4—C3—C2123.0 (9)C8A—C27—C28A113.9 (17)
C2—C1—C20178.4 (10)C30A—C27—C8121.0 (15)
C15—C16—C19119.3 (9)C30A—C27—C2893.3 (19)
C17—C16—C15121.5 (9)C30A—C27—C3025.7 (14)
C17—C16—C19119.1 (9)C30A—C27—C8A102.2 (15)
O1—C5—C6123.1 (9)C30A—C27—C29A113.4 (14)
O1—C5—C4121.1 (8)C30A—C27—C28A106.2 (13)
C6—C5—C4115.7 (7)C29A—C27—C8109.5 (13)
H7AA—C7—H7AB107.5C29A—C27—C28115.7 (19)
H7AA—C7—H7BC125.3C29A—C27—C3095.1 (15)
H7AA—C7—H7BD22.0C29A—C27—C8A115.7 (13)
H7AB—C7—H7BC20.5C29A—C27—C28A105.3 (13)
H7AB—C7—H7BD87.6C28A—C27—C899.3 (16)
H7BC—C7—H7BD107.0C28A—C27—C2814 (2)
C6—C7—H7AA108.5C16—C19—H19A109.5
C6—C7—H7AB108.5C16—C19—H19B109.5
C6—C7—H7BC107.6C16—C19—H19C109.5
C6—C7—H7BD107.6H19A—C19—H19B109.5
C6—C7—C8115.1 (10)H19A—C19—H19C109.5
C8—C7—H7AA108.5H19B—C19—H19C109.5
C8—C7—H7AB108.5C24—C23—C22119.5 (11)
C8—C7—H7BC91.4C24—C23—C26119.3 (14)
C8—C7—H7BD125.3C22—C23—C26121.2 (10)
C8A—C7—H7AA89.0C7—C8—C27108.1 (12)
C8A—C7—H7AB121.3C7—C8—H8111.4
C8A—C7—H7BC107.6C27—C8—H8111.4
C8A—C7—H7BD107.6C9—C8—C7100.9 (13)
C8A—C7—C6118.9 (11)C9—C8—C27113.3 (14)
C8A—C7—C820.3 (11)C9—C8—H8111.4
C1—C2—C3175.7 (9)C23—C26—H26A109.5
C14—C13—C12119.3 (8)C23—C26—H26B109.5
C18—C13—C14120.8 (9)C23—C26—H26C109.5
C18—C13—C12119.9 (9)H26A—C26—H26B109.5
C13—C14—H14120.3H26A—C26—H26C109.5
C13—C14—C15119.5 (8)H26B—C26—H26C109.5
C15—C14—H14120.3C4—C9—C8107.9 (15)
C20—C25—H25120.2C4—C9—H9A110.1
C24—C25—C20119.6 (8)C4—C9—H9B110.1
C24—C25—H25120.2C8—C9—H9A110.1
C7—C6—C5121.8 (8)C8—C9—H9B110.1
C10—C6—C5114.9 (8)H9A—C9—H9B108.4
C10—C6—C7123.2 (8)C27—C29—H29A109.5
C13—C18—H18120.3C27—C29—H29B109.5
C13—C18—C17119.4 (10)C27—C29—H29C109.5
C17—C18—H18120.3C27—C28—H28A109.5
C16—C15—C14118.3 (9)C27—C28—H28B109.5
C16—C15—H15120.8C27—C28—H28C109.5
C14—C15—H15120.8C27—C30—H30A109.5
C3—C4—C5117.4 (8)C27—C30—H30B109.5
C3—C4—C9127.7 (11)C27—C30—H30C109.5
C3—C4—C9A116.4 (10)C4—C9A—H9AA109.4
C5—C4—C9A124.2 (10)C4—C9A—H9AB109.4
C9—C4—C5113.8 (10)H9AA—C9A—H9AB108.0
C9—C4—C9A26.3 (9)C8A—C9A—C4111.1 (15)
C11—C12—C13175.6 (11)C8A—C9A—H9AA109.4
C6—C10—H10117.5C8A—C9A—H9AB109.4
C6—C10—C11125.0 (9)C7—C8A—C27118.2 (14)
C11—C10—H10117.5C7—C8A—C9A125.1 (16)
C16—C17—C18120.6 (9)C7—C8A—H8A97.6
C16—C17—H17119.7C27—C8A—H8A97.6
C18—C17—H17119.7C9A—C8A—C27111.5 (13)
C25—C24—H24119.4C9A—C8A—H8A97.6
C23—C24—C25121.3 (12)C27—C30A—H30D109.5
C23—C24—H24119.4C27—C30A—H30E109.5
C12—C11—C10177.1 (10)C27—C30A—H30F109.5
C20—C21—H21119.2H30D—C30A—H30E109.5
C20—C21—C22121.6 (12)H30D—C30A—H30F109.5
C22—C21—H21119.2H30E—C30A—H30F109.5
C21—C22—H22120.0C27—C29A—H29D109.5
C21—C22—C23120.0 (9)C27—C29A—H29E109.5
C23—C22—H22120.0C27—C29A—H29F109.5
C8—C27—C28102.9 (16)H29D—C29A—H29E109.5
C29—C27—C8105.3 (14)H29D—C29A—H29F109.5
C29—C27—C2897.7 (18)H29E—C29A—H29F109.5
C29—C27—C30114.6 (17)C27—C28A—H28D109.5
C29—C27—C8A118.4 (15)C27—C28A—H28E109.5
C29—C27—C30A128.5 (17)C27—C28A—H28F109.5
C29—C27—C29A21.1 (13)H28D—C28A—H28E109.5
C29—C27—C28A85.9 (15)H28D—C28A—H28F109.5
C30—C27—C8115.8 (14)H28E—C28A—H28F109.5
2-(Furan-2-ylmethylene)-6-(3-phenylprop-2-yn-1-ylidene)cyclohexanone (5a) top
Crystal data top
C20H16O2Dx = 1.309 Mg m3
Mr = 288.33Synchrotron radiation, λ = 0.9699 Å
Orthorhombic, Pca21Cell parameters from 7860 reflections
a = 9.5892 (19) Åθ = 4–37°
b = 10.145 (2) ŵ = 0.19 mm1
c = 30.080 (6) ÅT = 100 K
V = 2926.2 (10) Å3Needle, yellow
Z = 80.4 × 0.03 × 0.02 mm
F(000) = 1216
Data collection top
Mar CCD
diffractometer
3732 reflections with I > 2σ(I)
phi scanRint = 0.091
Absorption correction: multi-scan
(SCALA; Evans, 2006)
θmax = 38.4°, θmin = 3.3°
Tmin = 0.945, Tmax = 0.999h = 1212
15016 measured reflectionsk = 1212
5675 independent reflectionsl = 3737
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.095 w = 1/[σ2(Fo2) + (0.010P)2 + 9.P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.250(Δ/σ)max < 0.001
S = 1.01Δρmax = 1.08 e Å3
5675 reflectionsΔρmin = 0.51 e Å3
397 parametersAbsolute structure: Flack x determined using 1267 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.3 (8)
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3773 (6)1.1962 (6)0.60435 (19)0.0235 (13)
O20.6231 (7)1.1074 (5)0.46728 (17)0.0321 (14)
C10.4773 (8)1.0691 (8)0.5291 (3)0.0256 (17)
H10.49431.15960.53520.031*
C20.4037 (10)1.0017 (6)0.5582 (3)0.016 (2)
C30.3486 (9)1.0772 (8)0.5991 (3)0.0280 (18)
C40.2561 (10)1.0075 (7)0.6306 (3)0.0170 (19)
C50.1852 (9)1.0857 (9)0.6609 (3)0.0286 (18)
H50.20421.17760.65970.034*
C60.0870 (10)1.0444 (10)0.6937 (3)0.0324 (19)
C70.0009 (10)1.0200 (9)0.7211 (3)0.024 (2)
C80.3732 (9)0.8555 (8)0.5571 (3)0.0299 (19)
H8A0.44920.80960.54100.036*
H8B0.28540.84020.54060.036*
C90.3599 (8)0.7976 (9)0.6040 (3)0.0176 (17)
H9A0.44590.81540.62120.021*
H9B0.34690.70090.60220.021*
C100.2312 (9)0.8624 (9)0.6278 (3)0.0293 (18)
H10A0.14510.84460.61060.035*
H10B0.21990.82490.65790.035*
C110.5339 (9)1.0156 (8)0.4886 (2)0.0153 (17)
C120.5244 (12)0.9110 (8)0.4620 (3)0.039 (2)
H120.47120.83390.46760.047*
C130.6084 (13)0.9348 (11)0.4233 (3)0.046 (3)
H130.61960.87690.39870.056*
C140.6659 (9)1.0491 (10)0.4280 (3)0.028 (2)
H140.72871.08770.40730.034*
C150.1028 (9)1.0083 (7)0.7571 (3)0.018 (2)
C160.1557 (9)0.8874 (9)0.7712 (3)0.023 (2)
H160.12140.80810.75840.028*
C170.2606 (9)0.8816 (9)0.8046 (3)0.0231 (19)
H170.29600.79880.81410.028*
C180.3108 (10)0.9968 (8)0.8232 (3)0.023 (2)
H180.38080.99280.84550.027*
C190.2593 (9)1.1191 (9)0.8096 (2)0.0221 (19)
H190.29391.19820.82240.027*
C200.1565 (9)1.1235 (10)0.7768 (3)0.0219 (19)
H200.12151.20670.76760.026*
O1A0.3796 (7)0.6955 (7)0.39805 (19)0.0315 (15)
O2A0.1242 (6)0.6094 (6)0.5347 (2)0.0315 (14)
C1A0.2759 (9)0.5684 (9)0.4724 (3)0.0302 (19)
H1A0.26290.65970.46670.036*
C2A0.3485 (9)0.4997 (6)0.4401 (3)0.016 (2)
C3A0.4058 (9)0.5748 (9)0.4033 (3)0.0282 (18)
C4A0.5040 (10)0.5033 (7)0.3713 (3)0.017 (2)
C5A0.5643 (8)0.5804 (9)0.3402 (3)0.0274 (18)
H5A0.54010.67120.33920.033*
C6A0.6634 (9)0.5310 (11)0.3084 (3)0.0291 (19)
C7A0.7484 (11)0.5075 (7)0.2786 (3)0.0202 (19)
C8A0.3756 (9)0.3530 (8)0.4451 (3)0.0281 (18)
H8AA0.45910.33850.46380.034*
H8AB0.29500.31020.45980.034*
C9A0.3981 (8)0.2935 (9)0.3996 (3)0.0204 (17)
H9AA0.31280.30550.38150.024*
H9AB0.41510.19770.40260.024*
C10A0.5218 (10)0.3571 (9)0.3756 (3)0.033 (2)
H10C0.60840.33830.39240.040*
H10D0.53130.31780.34570.040*
C11A0.2152 (11)0.5197 (9)0.5149 (3)0.029 (2)
C12A0.2334 (9)0.4121 (9)0.5398 (3)0.0318 (19)
H12A0.29150.33850.53380.038*
C13A0.1435 (9)0.4330 (9)0.5787 (3)0.0249 (18)
H13A0.12470.37230.60200.030*
C14A0.0934 (12)0.5561 (10)0.5743 (3)0.042 (3)
H14A0.04190.60030.59670.050*
C15A0.8550 (10)0.4980 (7)0.2462 (3)0.020 (2)
C16A0.8974 (9)0.3730 (9)0.2290 (3)0.0210 (19)
H16A0.85730.29380.24000.025*
C17A0.9965 (9)0.3696 (9)0.1966 (3)0.0230 (19)
H17A1.02420.28700.18460.028*
C18A1.0583 (11)0.4853 (9)0.1805 (3)0.026 (2)
H18A1.12880.48100.15840.032*
C19A1.0158 (10)0.6057 (10)0.1972 (3)0.029 (2)
H19A1.05780.68440.18650.035*
C20A0.9121 (9)0.6127 (9)0.2294 (3)0.0230 (19)
H20A0.88070.69600.23980.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.030 (3)0.016 (3)0.024 (3)0.004 (3)0.004 (2)0.000 (3)
O20.060 (4)0.015 (3)0.021 (3)0.002 (3)0.013 (3)0.000 (2)
C10.027 (4)0.023 (4)0.027 (4)0.002 (3)0.003 (3)0.003 (4)
C20.022 (5)0.016 (5)0.010 (3)0.001 (3)0.004 (3)0.002 (2)
C30.035 (5)0.021 (4)0.029 (4)0.001 (4)0.002 (3)0.005 (3)
C40.015 (4)0.011 (4)0.025 (5)0.004 (3)0.001 (3)0.000 (3)
C50.030 (4)0.030 (5)0.025 (4)0.003 (4)0.001 (3)0.006 (4)
C60.036 (5)0.031 (5)0.030 (4)0.003 (4)0.006 (4)0.004 (4)
C70.023 (5)0.030 (5)0.020 (4)0.003 (3)0.006 (4)0.007 (4)
C80.037 (5)0.019 (4)0.034 (4)0.002 (4)0.005 (4)0.001 (4)
C90.023 (4)0.015 (4)0.015 (3)0.002 (3)0.002 (3)0.002 (3)
C100.034 (4)0.028 (5)0.026 (4)0.002 (4)0.003 (3)0.002 (3)
C110.010 (4)0.030 (4)0.006 (3)0.001 (3)0.001 (3)0.000 (3)
C120.081 (7)0.017 (4)0.019 (4)0.021 (5)0.015 (4)0.006 (3)
C130.087 (8)0.030 (6)0.022 (4)0.017 (5)0.018 (5)0.000 (4)
C140.032 (5)0.036 (6)0.017 (4)0.007 (4)0.003 (3)0.002 (4)
C150.009 (4)0.028 (5)0.016 (4)0.002 (3)0.002 (3)0.002 (3)
C160.032 (5)0.020 (5)0.017 (4)0.007 (4)0.009 (3)0.011 (4)
C170.028 (4)0.026 (5)0.015 (4)0.007 (4)0.003 (3)0.001 (3)
C180.021 (5)0.034 (6)0.014 (4)0.002 (3)0.002 (4)0.003 (3)
C190.026 (4)0.031 (5)0.010 (3)0.007 (4)0.002 (3)0.002 (3)
C200.028 (5)0.022 (5)0.016 (4)0.006 (4)0.007 (3)0.003 (3)
O1A0.049 (4)0.022 (4)0.024 (3)0.008 (3)0.005 (3)0.007 (3)
O2A0.033 (3)0.028 (3)0.034 (3)0.006 (3)0.003 (3)0.004 (3)
C1A0.034 (5)0.030 (5)0.026 (4)0.007 (4)0.005 (3)0.003 (4)
C2A0.012 (4)0.017 (5)0.017 (4)0.001 (3)0.009 (3)0.001 (3)
C3A0.035 (5)0.027 (4)0.023 (4)0.004 (4)0.003 (3)0.001 (3)
C4A0.016 (4)0.027 (5)0.009 (3)0.001 (3)0.006 (3)0.002 (3)
C5A0.031 (5)0.025 (4)0.026 (4)0.006 (4)0.001 (3)0.001 (3)
C6A0.026 (4)0.049 (5)0.012 (4)0.006 (4)0.002 (3)0.002 (4)
C7A0.020 (4)0.028 (5)0.013 (3)0.002 (3)0.008 (3)0.002 (3)
C8A0.041 (5)0.020 (4)0.024 (4)0.000 (4)0.002 (3)0.000 (3)
C9A0.028 (4)0.016 (4)0.018 (4)0.003 (3)0.000 (3)0.006 (3)
C10A0.041 (5)0.024 (5)0.035 (4)0.002 (4)0.003 (4)0.006 (4)
C11A0.029 (5)0.029 (5)0.029 (5)0.007 (4)0.002 (4)0.002 (4)
C12A0.025 (4)0.031 (5)0.039 (4)0.001 (4)0.003 (4)0.006 (4)
C13A0.037 (5)0.017 (4)0.021 (4)0.001 (3)0.006 (3)0.007 (3)
C14A0.087 (8)0.019 (5)0.019 (4)0.021 (5)0.020 (4)0.006 (4)
C15A0.025 (5)0.021 (5)0.015 (4)0.001 (3)0.004 (4)0.000 (3)
C16A0.024 (4)0.016 (4)0.023 (4)0.005 (3)0.009 (3)0.004 (3)
C17A0.025 (4)0.018 (4)0.026 (4)0.004 (3)0.006 (3)0.000 (4)
C18A0.028 (5)0.036 (6)0.015 (4)0.001 (4)0.004 (4)0.002 (3)
C19A0.037 (5)0.024 (5)0.027 (4)0.009 (4)0.005 (4)0.008 (4)
C20A0.025 (4)0.020 (5)0.024 (4)0.007 (4)0.006 (3)0.001 (4)
Geometric parameters (Å, º) top
O1—C31.249 (10)O1A—C3A1.260 (11)
O2—C111.418 (10)O2A—C11A1.395 (11)
O2—C141.384 (9)O2A—C14A1.340 (10)
C1—H10.9500C1A—H1A0.9500
C1—C21.317 (11)C1A—C2A1.385 (12)
C1—C111.438 (11)C1A—C11A1.488 (13)
C2—C31.541 (12)C2A—C3A1.452 (12)
C2—C81.512 (10)C2A—C8A1.519 (10)
C3—C41.480 (12)C3A—C4A1.528 (12)
C4—C51.387 (12)C4A—C5A1.351 (12)
C4—C101.494 (11)C4A—C10A1.499 (11)
C5—H50.9500C5A—H5A0.9500
C5—C61.427 (12)C5A—C6A1.438 (12)
C6—C71.203 (13)C6A—C7A1.234 (13)
C7—C151.464 (13)C7A—C15A1.416 (14)
C8—H8A0.9900C8A—H8AA0.9900
C8—H8B0.9900C8A—H8AB0.9900
C8—C91.534 (12)C8A—C9A1.513 (11)
C9—H9A0.9900C9A—H9AA0.9900
C9—H9B0.9900C9A—H9AB0.9900
C9—C101.570 (11)C9A—C10A1.530 (12)
C10—H10A0.9900C10A—H10C0.9900
C10—H10B0.9900C10A—H10D0.9900
C11—C121.333 (11)C11A—C12A1.335 (13)
C12—H120.9500C12A—H12A0.9500
C12—C131.435 (12)C12A—C13A1.466 (11)
C13—H130.9500C13A—H13A0.9500
C13—C141.292 (16)C13A—C14A1.345 (14)
C14—H140.9500C14A—H14A0.9500
C15—C161.393 (12)C15A—C16A1.428 (12)
C15—C201.409 (13)C15A—C20A1.382 (12)
C16—H160.9500C16A—H16A0.9500
C16—C171.423 (12)C16A—C17A1.363 (11)
C17—H170.9500C17A—H17A0.9500
C17—C181.383 (12)C17A—C18A1.401 (13)
C18—H180.9500C18A—H18A0.9500
C18—C191.397 (12)C18A—C19A1.382 (14)
C19—H190.9500C19A—H19A0.9500
C19—C201.394 (12)C19A—C20A1.390 (12)
C20—H200.9500C20A—H20A0.9500
C14—O2—C11106.5 (6)C14A—O2A—C11A104.7 (7)
C2—C1—H1117.6C2A—C1A—H1A115.4
C2—C1—C11124.7 (8)C2A—C1A—C11A129.3 (8)
C11—C1—H1117.6C11A—C1A—H1A115.4
C1—C2—C3117.2 (7)C1A—C2A—C3A117.5 (7)
C1—C2—C8126.7 (8)C1A—C2A—C8A120.6 (8)
C8—C2—C3116.1 (7)C3A—C2A—C8A121.7 (8)
O1—C3—C2120.4 (7)O1A—C3A—C2A122.0 (8)
O1—C3—C4120.8 (7)O1A—C3A—C4A120.4 (7)
C4—C3—C2118.7 (7)C2A—C3A—C4A117.6 (7)
C3—C4—C10121.9 (8)C5A—C4A—C3A115.2 (7)
C5—C4—C3116.3 (7)C5A—C4A—C10A125.7 (8)
C5—C4—C10121.6 (8)C10A—C4A—C3A119.0 (8)
C4—C5—H5116.2C4A—C5A—H5A118.6
C4—C5—C6127.6 (9)C4A—C5A—C6A122.9 (8)
C6—C5—H5116.2C6A—C5A—H5A118.6
C7—C6—C5174.5 (11)C7A—C6A—C5A170.5 (10)
C6—C7—C15171.9 (10)C6A—C7A—C15A171.7 (9)
C2—C8—H8A109.3C2A—C8A—H8AA109.9
C2—C8—H8B109.3C2A—C8A—H8AB109.9
C2—C8—C9111.7 (7)H8AA—C8A—H8AB108.3
H8A—C8—H8B107.9C9A—C8A—C2A108.9 (7)
C9—C8—H8A109.3C9A—C8A—H8AA109.9
C9—C8—H8B109.3C9A—C8A—H8AB109.9
C8—C9—H9A109.9C8A—C9A—H9AA109.3
C8—C9—H9B109.9C8A—C9A—H9AB109.3
C8—C9—C10108.9 (7)C8A—C9A—C10A111.6 (7)
H9A—C9—H9B108.3H9AA—C9A—H9AB108.0
C10—C9—H9A109.9C10A—C9A—H9AA109.3
C10—C9—H9B109.9C10A—C9A—H9AB109.3
C4—C10—C9108.3 (7)C4A—C10A—C9A111.7 (7)
C4—C10—H10A110.0C4A—C10A—H10C109.3
C4—C10—H10B110.0C4A—C10A—H10D109.3
C9—C10—H10A110.0C9A—C10A—H10C109.3
C9—C10—H10B110.0C9A—C10A—H10D109.3
H10A—C10—H10B108.4H10C—C10A—H10D107.9
O2—C11—C1111.3 (7)O2A—C11A—C1A113.2 (8)
C12—C11—O2107.0 (7)C12A—C11A—O2A112.0 (9)
C12—C11—C1141.6 (8)C12A—C11A—C1A134.6 (9)
C11—C12—H12125.8C11A—C12A—H12A127.7
C11—C12—C13108.4 (8)C11A—C12A—C13A104.6 (8)
C13—C12—H12125.8C13A—C12A—H12A127.7
C12—C13—H13126.2C12A—C13A—H13A127.3
C14—C13—C12107.5 (8)C14A—C13A—C12A105.4 (7)
C14—C13—H13126.2C14A—C13A—H13A127.3
O2—C14—H14124.7O2A—C14A—C13A112.5 (7)
C13—C14—O2110.5 (8)O2A—C14A—H14A123.7
C13—C14—H14124.7C13A—C14A—H14A123.7
C16—C15—C7122.7 (8)C7A—C15A—C16A121.0 (7)
C16—C15—C20117.9 (9)C20A—C15A—C7A118.7 (7)
C20—C15—C7119.3 (7)C20A—C15A—C16A120.2 (9)
C15—C16—H16119.7C15A—C16A—H16A120.6
C15—C16—C17120.6 (8)C17A—C16A—C15A118.7 (9)
C17—C16—H16119.7C17A—C16A—H16A120.6
C16—C17—H17120.1C16A—C17A—H17A119.3
C18—C17—C16119.8 (9)C16A—C17A—C18A121.4 (9)
C18—C17—H17120.1C18A—C17A—H17A119.3
C17—C18—H18119.7C17A—C18A—H18A120.3
C17—C18—C19120.6 (9)C19A—C18A—C17A119.4 (9)
C19—C18—H18119.7C19A—C18A—H18A120.3
C18—C19—H19120.5C18A—C19A—H19A119.7
C20—C19—C18119.1 (9)C18A—C19A—C20A120.6 (9)
C20—C19—H19120.5C20A—C19A—H19A119.7
C15—C20—H20119.0C15A—C20A—C19A119.7 (9)
C19—C20—C15122.0 (9)C15A—C20A—H20A120.2
C19—C20—H20119.0C19A—C20A—H20A120.2
O1—C3—C4—C511.0 (13)O1A—C3A—C4A—C5A4.0 (12)
O1—C3—C4—C10173.8 (8)O1A—C3A—C4A—C10A173.9 (8)
O2—C11—C12—C130.3 (11)O2A—C11A—C12A—C13A1.4 (11)
C1—C2—C3—O12.1 (13)C1A—C2A—C3A—O1A7.1 (13)
C1—C2—C3—C4175.1 (8)C1A—C2A—C3A—C4A171.1 (7)
C1—C2—C8—C9148.5 (9)C1A—C2A—C8A—C9A156.0 (8)
C1—C11—C12—C13173.9 (11)C1A—C11A—C12A—C13A177.2 (11)
C2—C1—C11—O2172.2 (8)C2A—C1A—C11A—O2A167.1 (8)
C2—C1—C11—C1214.3 (19)C2A—C1A—C11A—C12A17.1 (19)
C2—C3—C4—C5166.2 (8)C2A—C3A—C4A—C5A174.2 (7)
C2—C3—C4—C109.0 (13)C2A—C3A—C4A—C10A8.0 (12)
C2—C8—C9—C1063.7 (9)C2A—C8A—C9A—C10A59.4 (9)
C3—C2—C8—C928.3 (10)C3A—C2A—C8A—C9A28.6 (11)
C3—C4—C5—C6177.8 (8)C3A—C4A—C5A—C6A177.6 (7)
C3—C4—C10—C925.1 (12)C3A—C4A—C10A—C9A22.1 (12)
C5—C4—C10—C9160.0 (8)C5A—C4A—C10A—C9A155.5 (9)
C7—C15—C16—C17176.4 (9)C7A—C15A—C16A—C17A177.4 (9)
C7—C15—C20—C19176.5 (9)C7A—C15A—C20A—C19A179.3 (9)
C8—C2—C3—O1175.0 (8)C8A—C2A—C3A—O1A177.4 (8)
C8—C2—C3—C47.8 (12)C8A—C2A—C3A—C4A4.5 (12)
C8—C9—C10—C460.7 (9)C8A—C9A—C10A—C4A57.1 (10)
C10—C4—C5—C62.6 (14)C10A—C4A—C5A—C6A4.6 (14)
C11—O2—C14—C131.9 (10)C11A—O2A—C14A—C13A7.8 (12)
C11—C1—C2—C3178.5 (7)C11A—C1A—C2A—C3A175.2 (8)
C11—C1—C2—C84.8 (15)C11A—C1A—C2A—C8A0.3 (14)
C11—C12—C13—C140.9 (13)C11A—C12A—C13A—C14A5.9 (11)
C12—C13—C14—O21.7 (12)C12A—C13A—C14A—O2A8.7 (12)
C14—O2—C11—C1177.0 (7)C14A—O2A—C11A—C1A173.1 (9)
C14—O2—C11—C121.3 (9)C14A—O2A—C11A—C12A3.6 (11)
C15—C16—C17—C180.0 (13)C15A—C16A—C17A—C18A1.1 (13)
C16—C15—C20—C190.0 (13)C16A—C15A—C20A—C19A3.0 (14)
C16—C17—C18—C190.0 (14)C16A—C17A—C18A—C19A1.5 (15)
C17—C18—C19—C200.0 (13)C17A—C18A—C19A—C20A0.4 (15)
C18—C19—C20—C150.0 (12)C18A—C19A—C20A—C15A2.6 (14)
C20—C15—C16—C170.0 (13)C20A—C15A—C16A—C17A1.2 (14)
6-(3-Butylprop-2-yn-1-ylidene)-2-(furan-2-ylmethylene)cyclohexanone (5b) top
Crystal data top
C18H20O2Z = 2
Mr = 268.34F(000) = 288
Triclinic, P1Dx = 1.203 Mg m3
a = 9.2801 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5498 (14) ÅCell parameters from 2852 reflections
c = 9.6407 (14) Åθ = 2.3–34.7°
α = 84.218 (3)°µ = 0.08 mm1
β = 70.882 (3)°T = 120 K
γ = 66.632 (3)°Prism, yellow
V = 740.63 (19) Å30.4 × 0.3 × 0.2 mm
Data collection top
Bruker SMART APEX CCD area detector
diffractometer
6779 independent reflections
Radiation source: sealed tube4496 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8 pixels mm-1θmax = 36.1°, θmin = 2.3°
ω and φ scansh = 1515
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
k = 1515
Tmin = 0.669, Tmax = 0.747l = 1515
13735 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.050P)2 + 0.150P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
6779 reflectionsΔρmax = 0.45 e Å3
182 parametersΔρmin = 0.32 e Å3
0 restraints
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.23655 (10)0.69376 (8)0.12731 (9)0.02436 (17)
O20.06610 (10)0.31249 (8)0.04610 (9)0.02500 (17)
C10.33819 (12)0.58373 (11)0.16766 (11)0.01795 (18)
C20.46380 (12)0.60414 (11)0.21891 (11)0.01820 (18)
C30.60114 (13)0.46600 (12)0.24468 (13)0.0239 (2)
H3A0.64850.49390.31080.029*
H3B0.68980.42680.15020.029*
C40.53785 (15)0.34239 (12)0.31322 (13)0.0248 (2)
H4A0.45140.38080.40900.030*
H4B0.62970.25240.33100.030*
C50.46633 (13)0.29535 (11)0.21279 (12)0.0210 (2)
H5A0.55760.24040.12470.025*
H5B0.41480.22390.26490.025*
C60.33968 (12)0.42801 (11)0.16475 (11)0.01714 (18)
C70.22526 (12)0.41645 (11)0.11416 (11)0.01856 (18)
H70.15030.50990.09050.022*
C80.20164 (12)0.28237 (11)0.09137 (11)0.01880 (18)
C90.27716 (13)0.12861 (11)0.10131 (12)0.0217 (2)
H90.37370.07650.12940.026*
C100.18437 (14)0.06108 (12)0.06178 (13)0.0259 (2)
H100.20610.04470.05880.031*
C110.05936 (15)0.17637 (13)0.02933 (14)0.0282 (2)
H110.02250.16390.00120.034*
C120.44379 (13)0.74814 (12)0.24116 (12)0.0217 (2)
H120.35010.82750.22420.026*
C130.55011 (14)0.79231 (12)0.28780 (12)0.0232 (2)
C140.63463 (14)0.83827 (13)0.32581 (13)0.0250 (2)
C150.73884 (15)0.88956 (13)0.37614 (14)0.0270 (2)
H15A0.66740.96640.45730.032*
H15B0.79520.94020.29460.032*
C160.86873 (14)0.76120 (13)0.42901 (13)0.0250 (2)
H16A0.81340.70830.50880.030*
H16B0.94350.68610.34710.030*
C170.96963 (16)0.82046 (16)0.48471 (15)0.0330 (3)
H17A0.89370.90130.56130.040*
H17B1.03080.86700.40270.040*
C181.09177 (17)0.69700 (19)0.54821 (16)0.0439 (4)
H18A1.16860.61730.47260.066*
H18B1.03180.65250.63140.066*
H18C1.15390.74140.58170.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0267 (4)0.0158 (3)0.0373 (4)0.0081 (3)0.0200 (3)0.0052 (3)
O20.0258 (4)0.0167 (3)0.0397 (5)0.0077 (3)0.0207 (3)0.0030 (3)
C10.0185 (4)0.0170 (4)0.0197 (4)0.0070 (3)0.0080 (3)0.0020 (3)
C20.0188 (4)0.0185 (4)0.0192 (4)0.0078 (3)0.0082 (4)0.0029 (3)
C30.0221 (5)0.0211 (5)0.0335 (6)0.0082 (4)0.0162 (4)0.0046 (4)
C40.0293 (5)0.0206 (5)0.0306 (6)0.0101 (4)0.0184 (5)0.0076 (4)
C50.0235 (5)0.0150 (4)0.0264 (5)0.0063 (4)0.0123 (4)0.0032 (4)
C60.0186 (4)0.0152 (4)0.0185 (4)0.0068 (3)0.0070 (3)0.0019 (3)
C70.0195 (4)0.0148 (4)0.0217 (5)0.0062 (3)0.0076 (4)0.0017 (3)
C80.0181 (4)0.0171 (4)0.0234 (5)0.0066 (3)0.0097 (4)0.0015 (3)
C90.0218 (5)0.0161 (4)0.0296 (5)0.0058 (4)0.0132 (4)0.0014 (4)
C100.0291 (5)0.0163 (4)0.0377 (6)0.0085 (4)0.0178 (5)0.0011 (4)
C110.0312 (6)0.0200 (5)0.0434 (7)0.0118 (4)0.0219 (5)0.0015 (4)
C120.0230 (5)0.0206 (5)0.0257 (5)0.0096 (4)0.0119 (4)0.0025 (4)
C130.0259 (5)0.0206 (5)0.0265 (5)0.0102 (4)0.0115 (4)0.0020 (4)
C140.0272 (5)0.0237 (5)0.0281 (5)0.0111 (4)0.0120 (4)0.0005 (4)
C150.0291 (6)0.0259 (5)0.0338 (6)0.0138 (4)0.0150 (5)0.0015 (4)
C160.0226 (5)0.0272 (5)0.0284 (5)0.0115 (4)0.0091 (4)0.0007 (4)
C170.0296 (6)0.0426 (7)0.0345 (6)0.0175 (5)0.0144 (5)0.0028 (5)
C180.0293 (7)0.0655 (10)0.0373 (7)0.0153 (7)0.0158 (6)0.0046 (7)
Geometric parameters (Å, º) top
O1—C11.2317 (12)C9—C101.4169 (15)
O2—C81.3793 (12)C10—H100.9500
O2—C111.3540 (13)C10—C111.3457 (15)
C1—C21.4892 (14)C11—H110.9500
C1—C61.4847 (13)C12—H120.9500
C2—C31.4947 (14)C12—C131.4187 (15)
C2—C121.3424 (14)C13—C141.1982 (15)
C3—H3A0.9900C14—C151.4635 (15)
C3—H3B0.9900C15—H15A0.9900
C3—C41.5211 (15)C15—H15B0.9900
C4—H4A0.9900C15—C161.5231 (16)
C4—H4B0.9900C16—H16A0.9900
C4—C51.5248 (15)C16—H16B0.9900
C5—H5A0.9900C16—C171.5154 (16)
C5—H5B0.9900C17—H17A0.9900
C5—C61.5026 (13)C17—H17B0.9900
C6—C71.3494 (14)C17—C181.5161 (19)
C7—H70.9500C18—H18A0.9800
C7—C81.4306 (14)C18—H18B0.9800
C8—C91.3623 (14)C18—H18C0.9800
C9—H90.9500
C11—O2—C8106.96 (8)C10—C9—H9126.5
O1—C1—C2120.48 (9)C9—C10—H10126.8
O1—C1—C6120.95 (9)C11—C10—C9106.45 (9)
C6—C1—C2118.56 (8)C11—C10—H10126.8
C1—C2—C3119.03 (9)O2—C11—H11124.6
C12—C2—C1116.87 (9)C10—C11—O2110.78 (10)
C12—C2—C3124.09 (9)C10—C11—H11124.6
C2—C3—H3A109.6C2—C12—H12117.1
C2—C3—H3B109.6C2—C12—C13125.79 (10)
C2—C3—C4110.44 (9)C13—C12—H12117.1
H3A—C3—H3B108.1C14—C13—C12176.18 (12)
C4—C3—H3A109.6C13—C14—C15177.80 (12)
C4—C3—H3B109.6C14—C15—H15A108.8
C3—C4—H4A109.5C14—C15—H15B108.8
C3—C4—H4B109.5C14—C15—C16113.67 (9)
C3—C4—C5110.80 (9)H15A—C15—H15B107.7
H4A—C4—H4B108.1C16—C15—H15A108.8
C5—C4—H4A109.5C16—C15—H15B108.8
C5—C4—H4B109.5C15—C16—H16A109.3
C4—C5—H5A108.9C15—C16—H16B109.3
C4—C5—H5B108.9H16A—C16—H16B107.9
H5A—C5—H5B107.7C17—C16—C15111.74 (10)
C6—C5—C4113.29 (8)C17—C16—H16A109.3
C6—C5—H5A108.9C17—C16—H16B109.3
C6—C5—H5B108.9C16—C17—H17A109.0
C1—C6—C5119.92 (9)C16—C17—H17B109.0
C7—C6—C1115.73 (8)C16—C17—C18113.00 (12)
C7—C6—C5124.33 (9)H17A—C17—H17B107.8
C6—C7—H7115.7C18—C17—H17A109.0
C6—C7—C8128.70 (9)C18—C17—H17B109.0
C8—C7—H7115.7C17—C18—H18A109.5
O2—C8—C7113.56 (8)C17—C18—H18B109.5
C9—C8—O2108.80 (9)C17—C18—H18C109.5
C9—C8—C7137.64 (10)H18A—C18—H18B109.5
C8—C9—H9126.5H18A—C18—H18C109.5
C8—C9—C10107.02 (9)H18B—C18—H18C109.5
Selected geometrical parameters (Å and °)a top
R1R2nα1α2r1r2r3
3aPhH06.76 (8)1.46 (8)1.340 (4)–1.346 (4)1.470 (3)–1.474 (3)1.413 (4)–1.415 (4)
3b4-BrC6H4H13.20 (6)59.50 (6)1.360 (12)1.490 (2)–1.510 (2)1.420 (2)–1.430 (2)
3cPhH07.72 (8)10.79 (8)1.337 (3)–1.338 (3)1.483 (3)–1.488 (3)1.413 (3)–1.416 (3)
3d4-BrC6H4H15.30 (4)5.30 (4)1.348 (12)1.487 (9)–1.489 (11)1.405 (13)
3ePht-Bu136.53 (8)27.78 (8)1.323 (2)–1.346 (2)1.478 (2)–1.483 (2)1.416 (2)–1.417 (2)
3f4-MeC6H4t-Bu19.00 (4)24.50 (4)1.34 (1)–1.37 (1)1.50 (1)–1.52 (1)1.42 (1)–1.44 (2)
5aPhH18.10–9.90 (4)13.70–17.10 (3)1.32 (1)–1.39 (1)1.45 (2)–1.54 (1)1.43 (1)–1.44 (1)
5bn-BuH11.61 (7)5.46 (4)1.348 (3)–1.353 (3)1.490 (3)–1.493 (3)1.422 (3)–1.436 (3)
Note: (a) geometrical parameters are depicted in Scheme 2.
 

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