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1,3-Enyne structural motifs are versatile building blocks in organic synthesis and occur widely in various natural products with many of them being highly active as cytotoxic macrolides and anti­tumour anti­biotics. This article presents the crystal structure of three 1,1,4-triphenyl-substituted 1,3-enynes, viz. 4-(2-methyl­phen­yl)-1,1-diphenylbut-1-en-3-yne, C23H18 (1), 4-(2-meth­oxy­phen­yl)-1,1-diphenylbut-1-en-3-yne, C23H18O (2), and 4-(4-nitro­phen­yl)-1,1-diphenylbut-1-en-3-yne, C22H15NO2 (3). The benzene ring at position 4 of the but-1-en-3-yne group bears a weakly activating methyl group in com­pound 1, a moderately activating meth­oxy group in 2 and a strongly deactivating nitro group in 3. The crystal structures of 1 and 3 both have monoclinic symmetry, while that of 2 is ortho­rhom­bic, and all of them have one mol­ecule in the asymmetric unit. All three com­pounds were investigated for their anti­bacterial and anti­fungal activities. Inter­estingly, enyne 2 is the only com­pound tested that inhibited the growth of Aspergillus niger.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619016127/qs3087sup1.cif
Contains datablocks global, JCP_07S, JCP_10S, JCP_06S

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619016127/qs3087JCP_06Ssup2.hkl
Contains datablock JCP_06S

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619016127/qs3087JCP_07Ssup3.hkl
Contains datablock JCP_07S

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619016127/qs3087JCP_10Ssup4.hkl
Contains datablock JCP_10S

CCDC references: 1894246; 1887111; 1882656

Computing details top

For all structures, data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: shelXle (Hübschle et al., 2011); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b) and Mercury (Macrae et al., 2008).

4-(2-Methylphenyl)-1,1-diphenylbut-1-en-3-yne (JCP_06S) top
Crystal data top
C23H18F(000) = 624
Mr = 294.37Dx = 1.231 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 14.3054 (3) ÅCell parameters from 5897 reflections
b = 5.8354 (1) Åθ = 3.8–68.2°
c = 19.0365 (4) ŵ = 0.52 mm1
β = 90.935 (1)°T = 100 K
V = 1588.91 (5) Å3Block, clear light yellow
Z = 40.25 × 0.15 × 0.10 mm
Data collection top
Bruker D8 Venture
diffractometer
2897 independent reflections
Radiation source: Incoatec Microsource2201 reflections with I > 2σ(I)
Mirrors monochromatorRint = 0.070
Detector resolution: 10.4167 pixels mm-1θmax = 68.3°, θmin = 3.8°
ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
k = 77
Tmin = 0.672, Tmax = 0.753l = 2221
21068 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.3848P]
where P = (Fo2 + 2Fc2)/3
2897 reflections(Δ/σ)max < 0.001
209 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.27 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.62818 (12)0.4676 (3)0.34132 (9)0.0187 (4)
C20.52879 (12)0.5072 (3)0.32097 (9)0.0189 (4)
C30.50023 (12)0.7070 (3)0.28601 (10)0.0219 (4)
H30.54490.82240.27590.026*
C40.40756 (12)0.7384 (3)0.26599 (10)0.0237 (4)
H40.38940.87380.24160.028*
C50.34105 (12)0.5730 (3)0.28136 (9)0.0244 (4)
H50.27750.59480.26770.029*
C60.36825 (12)0.3761 (3)0.31683 (9)0.0228 (4)
H60.32290.26330.32790.027*
C70.46079 (12)0.3424 (3)0.33628 (9)0.0208 (4)
H70.47850.2060.36030.025*
C80.64544 (11)0.3118 (3)0.40258 (9)0.0185 (4)
C90.60968 (12)0.3669 (3)0.46846 (9)0.0213 (4)
H90.57770.50790.47480.026*
C100.62064 (13)0.2171 (3)0.52448 (10)0.0243 (4)
H100.59640.25580.56910.029*
C110.66701 (13)0.0108 (3)0.51541 (10)0.0249 (4)
H110.67440.09210.55380.03*
C120.70260 (12)0.0454 (3)0.45040 (10)0.0236 (4)
H120.73430.18690.44420.028*
C130.69196 (12)0.1047 (3)0.39437 (10)0.0216 (4)
H130.71670.06560.34990.026*
C140.69851 (12)0.5676 (3)0.30626 (9)0.0196 (4)
H140.68260.65280.26530.024*
C150.79494 (12)0.5547 (3)0.32617 (9)0.0200 (4)
C160.87627 (12)0.5582 (3)0.34320 (9)0.0215 (4)
C170.97189 (12)0.5445 (3)0.36746 (9)0.0206 (4)
C180.99968 (12)0.3543 (3)0.40849 (9)0.0225 (4)
C191.09221 (13)0.3434 (3)0.43234 (10)0.0268 (4)
H191.11230.21580.45970.032*
C201.15554 (13)0.5157 (3)0.41682 (10)0.0270 (4)
H201.21810.50640.43410.032*
C211.12775 (13)0.7009 (3)0.37624 (10)0.0261 (4)
H211.17120.81840.36560.031*
C221.03653 (12)0.7149 (3)0.35113 (10)0.0230 (4)
H221.01790.8410.32260.028*
C230.93035 (13)0.1711 (3)0.42587 (11)0.0276 (4)
H23A0.89930.11780.38260.041*
H23B0.88360.23330.45770.041*
H23C0.96280.04250.44860.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0219 (9)0.0155 (9)0.0189 (9)0.0004 (7)0.0019 (7)0.0036 (7)
C20.0210 (9)0.0191 (9)0.0166 (9)0.0006 (7)0.0012 (7)0.0015 (7)
C30.0211 (9)0.0208 (10)0.0237 (10)0.0006 (8)0.0030 (7)0.0012 (7)
C40.0245 (9)0.0238 (10)0.0229 (10)0.0057 (8)0.0021 (8)0.0038 (8)
C50.0199 (9)0.0326 (11)0.0208 (10)0.0021 (8)0.0006 (7)0.0004 (8)
C60.0213 (9)0.0260 (10)0.0211 (10)0.0041 (8)0.0006 (7)0.0006 (8)
C70.0237 (9)0.0200 (9)0.0186 (10)0.0003 (8)0.0003 (7)0.0000 (7)
C80.0140 (8)0.0187 (9)0.0227 (10)0.0021 (7)0.0008 (7)0.0003 (7)
C90.0184 (9)0.0216 (10)0.0239 (10)0.0009 (7)0.0009 (7)0.0016 (7)
C100.0266 (10)0.0262 (10)0.0203 (10)0.0027 (8)0.0020 (7)0.0004 (8)
C110.0263 (10)0.0247 (10)0.0235 (10)0.0025 (8)0.0016 (7)0.0068 (8)
C120.0225 (9)0.0186 (10)0.0298 (11)0.0004 (8)0.0011 (8)0.0017 (8)
C130.0208 (9)0.0201 (9)0.0238 (10)0.0002 (8)0.0031 (7)0.0004 (7)
C140.0204 (9)0.0185 (9)0.0199 (10)0.0029 (7)0.0000 (7)0.0014 (7)
C150.0229 (9)0.0179 (9)0.0195 (9)0.0017 (7)0.0043 (7)0.0006 (7)
C160.0243 (10)0.0195 (9)0.0209 (10)0.0004 (8)0.0049 (7)0.0004 (7)
C170.0199 (9)0.0222 (10)0.0199 (10)0.0003 (8)0.0028 (7)0.0043 (7)
C180.0241 (9)0.0230 (10)0.0204 (10)0.0015 (8)0.0029 (7)0.0022 (8)
C190.0244 (10)0.0300 (11)0.0258 (11)0.0033 (8)0.0015 (8)0.0015 (8)
C200.0190 (9)0.0345 (12)0.0275 (11)0.0009 (8)0.0019 (8)0.0024 (9)
C210.0208 (10)0.0289 (11)0.0286 (11)0.0040 (8)0.0034 (8)0.0034 (8)
C220.0251 (10)0.0222 (10)0.0219 (10)0.0002 (8)0.0034 (8)0.0014 (8)
C230.0262 (10)0.0250 (10)0.0316 (11)0.0005 (8)0.0026 (8)0.0044 (8)
Geometric parameters (Å, º) top
C1—C141.349 (2)C12—C131.387 (2)
C1—C21.486 (2)C12—H120.95
C1—C81.496 (2)C13—H130.95
C2—C31.400 (2)C14—C151.427 (2)
C2—C71.402 (2)C14—H140.95
C3—C41.385 (2)C15—C161.203 (3)
C3—H30.95C16—C171.439 (2)
C4—C51.390 (3)C17—C221.396 (2)
C4—H40.95C17—C181.411 (3)
C5—C61.385 (3)C18—C191.394 (3)
C5—H50.95C18—C231.499 (2)
C6—C71.383 (2)C19—C201.389 (3)
C6—H60.95C19—H190.95
C7—H70.95C20—C211.383 (3)
C8—C131.390 (2)C20—H200.95
C8—C91.400 (2)C21—C221.385 (2)
C9—C101.386 (3)C21—H210.95
C9—H90.95C22—H220.95
C10—C111.387 (3)C23—H23A0.98
C10—H100.95C23—H23B0.98
C11—C121.385 (3)C23—H23C0.98
C11—H110.95
C14—C1—C2121.47 (16)C11—C12—H12120.0
C14—C1—C8122.24 (16)C13—C12—H12120.0
C2—C1—C8116.29 (14)C12—C13—C8120.65 (17)
C3—C2—C7118.17 (16)C12—C13—H13119.7
C3—C2—C1121.62 (16)C8—C13—H13119.7
C7—C2—C1120.21 (16)C1—C14—C15124.86 (17)
C4—C3—C2120.76 (17)C1—C14—H14117.6
C4—C3—H3119.6C15—C14—H14117.6
C2—C3—H3119.6C16—C15—C14176.04 (19)
C3—C4—C5120.36 (17)C15—C16—C17174.8 (2)
C3—C4—H4119.8C22—C17—C18120.12 (16)
C5—C4—H4119.8C22—C17—C16121.25 (17)
C6—C5—C4119.40 (17)C18—C17—C16118.63 (16)
C6—C5—H5120.3C19—C18—C17118.30 (17)
C4—C5—H5120.3C19—C18—C23121.58 (17)
C7—C6—C5120.57 (17)C17—C18—C23120.12 (16)
C7—C6—H6119.7C20—C19—C18121.12 (18)
C5—C6—H6119.7C20—C19—H19119.4
C6—C7—C2120.73 (17)C18—C19—H19119.4
C6—C7—H7119.6C21—C20—C19120.15 (17)
C2—C7—H7119.6C21—C20—H20119.9
C13—C8—C9118.90 (17)C19—C20—H20119.9
C13—C8—C1120.94 (16)C20—C21—C22119.99 (18)
C9—C8—C1120.05 (15)C20—C21—H21120.0
C10—C9—C8120.41 (17)C22—C21—H21120.0
C10—C9—H9119.8C21—C22—C17120.32 (18)
C8—C9—H9119.8C21—C22—H22119.8
C9—C10—C11120.01 (18)C17—C22—H22119.8
C9—C10—H10120.0C18—C23—H23A109.5
C11—C10—H10120.0C18—C23—H23B109.5
C12—C11—C10120.02 (18)H23A—C23—H23B109.5
C12—C11—H11120.0C18—C23—H23C109.5
C10—C11—H11120.0H23A—C23—H23C109.5
C11—C12—C13120.01 (17)H23B—C23—H23C109.5
C14—C1—C2—C325.7 (3)C9—C10—C11—C120.2 (3)
C8—C1—C2—C3154.24 (16)C10—C11—C12—C130.1 (3)
C14—C1—C2—C7153.97 (17)C11—C12—C13—C80.2 (3)
C8—C1—C2—C726.1 (2)C9—C8—C13—C120.2 (3)
C7—C2—C3—C41.2 (3)C1—C8—C13—C12175.94 (16)
C1—C2—C3—C4178.46 (17)C2—C1—C14—C15174.16 (16)
C2—C3—C4—C51.0 (3)C8—C1—C14—C155.7 (3)
C3—C4—C5—C60.1 (3)C22—C17—C18—C190.6 (3)
C4—C5—C6—C70.7 (3)C16—C17—C18—C19179.42 (17)
C5—C6—C7—C20.5 (3)C22—C17—C18—C23179.84 (17)
C3—C2—C7—C60.5 (3)C16—C17—C18—C230.2 (3)
C1—C2—C7—C6179.20 (16)C17—C18—C19—C200.6 (3)
C14—C1—C8—C1364.2 (2)C23—C18—C19—C20179.02 (18)
C2—C1—C8—C13115.94 (18)C18—C19—C20—C210.9 (3)
C14—C1—C8—C9119.75 (19)C19—C20—C21—C220.2 (3)
C2—C1—C8—C960.2 (2)C20—C21—C22—C171.0 (3)
C13—C8—C9—C100.0 (3)C18—C17—C22—C211.3 (3)
C1—C8—C9—C10176.20 (16)C16—C17—C22—C21178.64 (17)
C8—C9—C10—C110.2 (3)
4-(2-Methoxyphenyl)-1,1-diphenylbut-1-en-3-yne (JCP_07S) top
Crystal data top
C23H18ODx = 1.205 Mg m3
Mr = 310.37Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, PbcaCell parameters from 9909 reflections
a = 10.6325 (2) Åθ = 4.1–68.3°
b = 14.7734 (2) ŵ = 0.56 mm1
c = 21.7751 (4) ÅT = 100 K
V = 3420.39 (10) Å3Block, clear light yellow
Z = 80.45 × 0.35 × 0.25 mm
F(000) = 1312
Data collection top
Bruker D8 Venture
diffractometer
3129 independent reflections
Radiation source: Incoatec Microsource2681 reflections with I > 2σ(I)
Mirrors monochromatorRint = 0.049
Detector resolution: 10.4167 pixels mm-1θmax = 68.3°, θmin = 4.1°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
k = 1717
Tmin = 0.663, Tmax = 0.753l = 2626
27165 measured reflections
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)] = 0.043H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0495P)2 + 1.7874P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3129 reflectionsΔρmax = 0.32 e Å3
219 parametersΔρmin = 0.25 e Å3
0 restraintsExtinction correction: SHELXL2014 (Sheldrick, 2015b)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00168 (17)
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
O10.81307 (10)0.58400 (7)0.40917 (5)0.0302 (3)
C10.35943 (14)0.36061 (9)0.40946 (6)0.0204 (3)
C20.32376 (13)0.27620 (10)0.44219 (7)0.0216 (3)
C30.25780 (14)0.20732 (10)0.41220 (8)0.0282 (4)
H30.23110.21560.37090.034*
C40.23109 (15)0.12685 (11)0.44246 (9)0.0369 (4)
H40.18740.080.42150.044*
C50.26775 (16)0.11423 (12)0.50312 (9)0.0397 (5)
H50.24960.05890.52360.048*
C60.33078 (16)0.18274 (12)0.53345 (8)0.0350 (4)
H60.35510.17470.57510.042*
C70.35865 (14)0.26295 (11)0.50356 (7)0.0271 (3)
H70.4020.30960.52490.033*
C80.26657 (14)0.40265 (9)0.36748 (6)0.0204 (3)
C90.13830 (14)0.40071 (10)0.38151 (7)0.0250 (3)
H90.11020.36830.41660.03*
C100.05153 (16)0.44541 (11)0.34487 (8)0.0317 (4)
H100.03530.44360.35510.038*
C110.09088 (17)0.49242 (11)0.29361 (8)0.0358 (4)
H110.03170.52430.26910.043*
C120.21694 (17)0.49281 (12)0.27806 (7)0.0360 (4)
H120.24410.5240.24230.043*
C130.30365 (16)0.44802 (11)0.31427 (7)0.0281 (4)
H130.38980.44810.30280.034*
C140.47479 (14)0.39614 (10)0.42026 (7)0.0237 (3)
H140.52760.36280.44720.028*
C150.52618 (14)0.47750 (10)0.39594 (7)0.0243 (3)
C160.57677 (14)0.54474 (10)0.37683 (7)0.0244 (3)
C170.63718 (15)0.62237 (10)0.35096 (7)0.0252 (3)
C180.76265 (16)0.64074 (10)0.36693 (7)0.0272 (4)
C190.82665 (17)0.71257 (12)0.33937 (8)0.0360 (4)
H190.91190.72450.34960.043*
C200.7645 (2)0.76611 (12)0.29700 (9)0.0429 (5)
H200.80830.81450.27780.051*
C210.64020 (18)0.75079 (12)0.28198 (8)0.0398 (4)
H210.59870.7890.25330.048*
C220.57572 (17)0.67880 (11)0.30908 (7)0.0319 (4)
H220.490.66820.2990.038*
C230.92553 (16)0.61278 (13)0.43930 (9)0.0396 (4)
H23A0.99480.61430.40960.059*
H23B0.9460.57040.47240.059*
H23C0.9130.67340.45650.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0213 (6)0.0309 (6)0.0383 (6)0.0055 (5)0.0060 (5)0.0005 (5)
C10.0194 (7)0.0196 (7)0.0221 (7)0.0009 (6)0.0013 (6)0.0032 (6)
C20.0148 (7)0.0205 (7)0.0295 (7)0.0023 (6)0.0027 (6)0.0010 (6)
C30.0199 (7)0.0235 (8)0.0412 (9)0.0004 (6)0.0014 (7)0.0006 (7)
C40.0212 (8)0.0213 (8)0.0682 (12)0.0019 (7)0.0051 (8)0.0000 (8)
C50.0249 (9)0.0290 (9)0.0651 (12)0.0082 (7)0.0166 (8)0.0193 (9)
C60.0281 (9)0.0393 (10)0.0377 (9)0.0115 (8)0.0098 (7)0.0141 (8)
C70.0222 (8)0.0299 (8)0.0293 (8)0.0046 (6)0.0040 (6)0.0021 (6)
C80.0220 (7)0.0183 (7)0.0209 (7)0.0020 (6)0.0018 (6)0.0029 (6)
C90.0229 (8)0.0234 (7)0.0285 (8)0.0012 (6)0.0016 (6)0.0018 (6)
C100.0235 (8)0.0297 (8)0.0420 (9)0.0003 (7)0.0077 (7)0.0022 (7)
C110.0358 (10)0.0322 (9)0.0393 (9)0.0031 (7)0.0173 (8)0.0068 (7)
C120.0424 (11)0.0388 (10)0.0267 (8)0.0109 (8)0.0098 (7)0.0087 (7)
C130.0286 (8)0.0326 (8)0.0230 (7)0.0074 (7)0.0023 (6)0.0006 (6)
C140.0195 (7)0.0219 (7)0.0296 (8)0.0000 (6)0.0013 (6)0.0012 (6)
C150.0174 (8)0.0254 (8)0.0301 (8)0.0002 (6)0.0009 (6)0.0021 (6)
C160.0202 (7)0.0256 (8)0.0273 (7)0.0003 (6)0.0006 (6)0.0049 (6)
C170.0252 (8)0.0230 (7)0.0275 (8)0.0017 (6)0.0039 (6)0.0051 (6)
C180.0294 (8)0.0243 (8)0.0278 (7)0.0019 (6)0.0031 (7)0.0036 (6)
C190.0316 (9)0.0341 (9)0.0424 (9)0.0092 (7)0.0062 (7)0.0043 (8)
C200.0515 (12)0.0321 (9)0.0450 (10)0.0069 (9)0.0089 (9)0.0054 (8)
C210.0470 (11)0.0333 (9)0.0391 (9)0.0017 (8)0.0011 (8)0.0071 (8)
C220.0362 (9)0.0277 (8)0.0320 (8)0.0054 (7)0.0014 (7)0.0020 (7)
C230.0254 (9)0.0441 (10)0.0493 (10)0.0057 (8)0.0095 (8)0.0023 (8)
Geometric parameters (Å, º) top
O1—C181.3550 (19)C11—C121.383 (3)
O1—C231.4287 (19)C11—H110.95
C1—C141.355 (2)C12—C131.382 (2)
C1—C81.482 (2)C12—H120.95
C1—C21.485 (2)C13—H130.95
C2—C31.398 (2)C14—C151.423 (2)
C2—C71.401 (2)C14—H140.95
C3—C41.388 (2)C15—C161.204 (2)
C3—H30.95C16—C171.430 (2)
C4—C51.390 (3)C17—C221.398 (2)
C4—H40.95C17—C181.405 (2)
C5—C61.382 (3)C18—C191.396 (2)
C5—H50.95C19—C201.383 (3)
C6—C71.384 (2)C19—H190.95
C6—H60.95C20—C211.380 (3)
C7—H70.95C20—H200.95
C8—C131.395 (2)C21—C221.396 (2)
C8—C91.398 (2)C21—H210.95
C9—C101.387 (2)C22—H220.95
C9—H90.95C23—H23A0.98
C10—C111.380 (2)C23—H23B0.98
C10—H100.95C23—H23C0.98
C18—O1—C23117.30 (13)C13—C12—H12119.8
C14—C1—C8123.22 (13)C11—C12—H12119.8
C14—C1—C2118.24 (13)C12—C13—C8121.01 (15)
C8—C1—C2118.53 (12)C12—C13—H13119.5
C3—C2—C7118.48 (14)C8—C13—H13119.5
C3—C2—C1121.01 (13)C1—C14—C15127.63 (14)
C7—C2—C1120.49 (13)C1—C14—H14116.2
C4—C3—C2120.28 (15)C15—C14—H14116.2
C4—C3—H3119.9C16—C15—C14175.94 (16)
C2—C3—H3119.9C15—C16—C17176.93 (16)
C3—C4—C5120.57 (16)C22—C17—C18119.35 (15)
C3—C4—H4119.7C22—C17—C16121.69 (15)
C5—C4—H4119.7C18—C17—C16118.94 (14)
C6—C5—C4119.47 (15)O1—C18—C19124.69 (15)
C6—C5—H5120.3O1—C18—C17115.10 (13)
C4—C5—H5120.3C19—C18—C17120.21 (15)
C5—C6—C7120.42 (16)C20—C19—C18119.24 (17)
C5—C6—H6119.8C20—C19—H19120.4
C7—C6—H6119.8C18—C19—H19120.4
C6—C7—C2120.76 (16)C21—C20—C19121.44 (17)
C6—C7—H7119.6C21—C20—H20119.3
C2—C7—H7119.6C19—C20—H20119.3
C13—C8—C9117.84 (14)C20—C21—C22119.67 (17)
C13—C8—C1121.68 (14)C20—C21—H21120.2
C9—C8—C1120.43 (13)C22—C21—H21120.2
C10—C9—C8120.89 (14)C21—C22—C17120.03 (17)
C10—C9—H9119.6C21—C22—H22120.0
C8—C9—H9119.6C17—C22—H22120.0
C11—C10—C9120.22 (16)O1—C23—H23A109.5
C11—C10—H10119.9O1—C23—H23B109.5
C9—C10—H10119.9H23A—C23—H23B109.5
C10—C11—C12119.62 (15)O1—C23—H23C109.5
C10—C11—H11120.2H23A—C23—H23C109.5
C12—C11—H11120.2H23B—C23—H23C109.5
C13—C12—C11120.34 (15)
C14—C1—C2—C3139.45 (15)C10—C11—C12—C131.4 (3)
C8—C1—C2—C341.58 (19)C11—C12—C13—C80.9 (3)
C14—C1—C2—C738.8 (2)C9—C8—C13—C122.7 (2)
C8—C1—C2—C7140.15 (14)C1—C8—C13—C12174.99 (14)
C7—C2—C3—C41.8 (2)C8—C1—C14—C151.5 (2)
C1—C2—C3—C4176.53 (14)C2—C1—C14—C15177.46 (14)
C2—C3—C4—C51.0 (2)C23—O1—C18—C1917.2 (2)
C3—C4—C5—C60.3 (2)C23—O1—C18—C17163.43 (14)
C4—C5—C6—C70.8 (2)C22—C17—C18—O1178.13 (13)
C5—C6—C7—C20.1 (2)C16—C17—C18—O13.5 (2)
C3—C2—C7—C61.3 (2)C22—C17—C18—C192.5 (2)
C1—C2—C7—C6176.99 (13)C16—C17—C18—C19175.83 (15)
C14—C1—C8—C1334.7 (2)O1—C18—C19—C20179.67 (15)
C2—C1—C8—C13146.42 (14)C17—C18—C19—C201.0 (2)
C14—C1—C8—C9142.96 (15)C18—C19—C20—C210.8 (3)
C2—C1—C8—C935.97 (19)C19—C20—C21—C221.2 (3)
C13—C8—C9—C102.4 (2)C20—C21—C22—C170.3 (3)
C1—C8—C9—C10175.33 (14)C18—C17—C22—C212.1 (2)
C8—C9—C10—C110.2 (2)C16—C17—C22—C21176.13 (15)
C9—C10—C11—C121.7 (3)
4-(4-Nitrophenyl)-1,1-diphenylbut-1-en-3-yne (JCP_10S) top
Crystal data top
C22H15NO2F(000) = 680
Mr = 325.36Dx = 1.321 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.6548 (5) ÅCell parameters from 9866 reflections
b = 22.2107 (10) Åθ = 2.8–27.5°
c = 7.9248 (4) ŵ = 0.09 mm1
β = 105.749 (1)°T = 100 K
V = 1635.60 (14) Å3Block, clear pale yellow
Z = 40.35 × 0.25 × 0.15 mm
Data collection top
Bruker D8 Venture
diffractometer
3763 independent reflections
Radiation source: Incoatec Microsource2822 reflections with I > 2σ(I)
Mirrors monochromatorRint = 0.046
Detector resolution: 10.4167 pixels mm-1θmax = 27.5°, θmin = 2.8°
ω scansh = 1212
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
k = 2828
Tmin = 0.717, Tmax = 0.746l = 1010
40247 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0437P)2 + 0.5574P]
where P = (Fo2 + 2Fc2)/3
3763 reflections(Δ/σ)max = 0.001
226 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.26 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
O11.06547 (11)0.57359 (5)1.24915 (14)0.0290 (3)
O20.96091 (10)0.66032 (4)1.23968 (13)0.0261 (2)
N10.96049 (12)0.60708 (5)1.19807 (15)0.0205 (3)
C10.23501 (14)0.39605 (6)0.47305 (16)0.0155 (3)
C20.35549 (14)0.35375 (6)0.54916 (16)0.0157 (3)
C30.32967 (14)0.29915 (6)0.62236 (17)0.0181 (3)
H30.23370.28780.61720.022*
C40.44266 (15)0.26120 (6)0.70263 (18)0.0209 (3)
H40.42380.22470.75480.025*
C50.58279 (15)0.27639 (6)0.70686 (18)0.0215 (3)
H50.660.25040.76170.026*
C60.60984 (15)0.32977 (6)0.63058 (18)0.0214 (3)
H60.70550.33990.63110.026*
C70.49756 (14)0.36836 (6)0.55356 (17)0.0181 (3)
H70.51720.40510.50320.022*
C80.09902 (14)0.37215 (6)0.35605 (16)0.0161 (3)
C90.09857 (15)0.32199 (6)0.24950 (17)0.0197 (3)
H90.18620.30140.25660.024*
C100.02771 (16)0.30173 (6)0.13340 (18)0.0244 (3)
H100.02590.26780.06120.029*
C110.15640 (15)0.33103 (7)0.12283 (18)0.0248 (3)
H110.24270.31780.04170.03*
C120.15856 (15)0.37963 (7)0.23106 (19)0.0257 (3)
H120.24710.39920.22620.031*
C130.03271 (14)0.40003 (6)0.34644 (18)0.0212 (3)
H130.03590.43350.42010.025*
C140.24632 (14)0.45581 (6)0.50884 (17)0.0181 (3)
H140.16930.48090.44760.022*
C150.36393 (15)0.48402 (6)0.63032 (17)0.0179 (3)
C160.46033 (14)0.50917 (6)0.73385 (17)0.0188 (3)
C170.58479 (14)0.53456 (6)0.85444 (17)0.0177 (3)
C180.70564 (15)0.49816 (6)0.92069 (17)0.0203 (3)
H180.70340.4570.88730.024*
C190.82814 (15)0.52171 (6)1.03438 (18)0.0200 (3)
H190.91030.49711.07980.024*
C200.82900 (14)0.58180 (6)1.08093 (16)0.0177 (3)
C210.71092 (14)0.61893 (6)1.01923 (17)0.0183 (3)
H210.7140.661.05390.022*
C220.58867 (14)0.59503 (6)0.90637 (17)0.0189 (3)
H220.50630.61980.86340.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0190 (5)0.0322 (6)0.0321 (6)0.0051 (4)0.0007 (4)0.0011 (5)
O20.0254 (6)0.0215 (5)0.0292 (6)0.0034 (4)0.0034 (4)0.0060 (4)
N10.0180 (6)0.0243 (6)0.0194 (6)0.0004 (5)0.0052 (5)0.0011 (5)
C10.0159 (7)0.0172 (7)0.0138 (6)0.0001 (5)0.0048 (5)0.0012 (5)
C20.0177 (7)0.0148 (6)0.0139 (6)0.0003 (5)0.0031 (5)0.0028 (5)
C30.0173 (7)0.0167 (7)0.0203 (7)0.0009 (5)0.0051 (5)0.0016 (5)
C40.0249 (8)0.0160 (7)0.0208 (7)0.0013 (6)0.0048 (6)0.0006 (5)
C50.0194 (7)0.0202 (7)0.0211 (7)0.0064 (6)0.0009 (6)0.0024 (6)
C60.0151 (7)0.0246 (7)0.0232 (7)0.0011 (6)0.0030 (6)0.0053 (6)
C70.0201 (7)0.0161 (6)0.0176 (6)0.0031 (5)0.0045 (5)0.0022 (5)
C80.0170 (7)0.0153 (6)0.0149 (6)0.0001 (5)0.0025 (5)0.0029 (5)
C90.0189 (7)0.0191 (7)0.0205 (7)0.0000 (5)0.0043 (5)0.0011 (5)
C100.0296 (8)0.0208 (7)0.0210 (7)0.0039 (6)0.0036 (6)0.0018 (6)
C110.0213 (8)0.0260 (8)0.0219 (7)0.0068 (6)0.0030 (6)0.0034 (6)
C120.0170 (7)0.0277 (8)0.0296 (8)0.0028 (6)0.0017 (6)0.0036 (6)
C130.0209 (7)0.0193 (7)0.0224 (7)0.0016 (6)0.0043 (6)0.0006 (6)
C140.0184 (7)0.0178 (7)0.0172 (6)0.0010 (5)0.0034 (5)0.0013 (5)
C150.0226 (7)0.0129 (6)0.0193 (6)0.0006 (5)0.0074 (6)0.0011 (5)
C160.0237 (7)0.0141 (6)0.0202 (7)0.0004 (5)0.0085 (6)0.0001 (5)
C170.0213 (7)0.0182 (7)0.0155 (6)0.0039 (6)0.0081 (5)0.0005 (5)
C180.0248 (8)0.0150 (6)0.0230 (7)0.0005 (6)0.0097 (6)0.0009 (5)
C190.0191 (7)0.0200 (7)0.0221 (7)0.0030 (5)0.0078 (5)0.0019 (6)
C200.0175 (7)0.0213 (7)0.0150 (6)0.0030 (5)0.0057 (5)0.0001 (5)
C210.0211 (7)0.0152 (6)0.0187 (6)0.0007 (5)0.0055 (5)0.0008 (5)
C220.0194 (7)0.0175 (7)0.0198 (7)0.0015 (5)0.0050 (5)0.0008 (5)
Geometric parameters (Å, º) top
O1—N11.2336 (14)C10—C111.385 (2)
O2—N11.2273 (15)C10—H100.95
N1—C201.4659 (17)C11—C121.382 (2)
C1—C141.3554 (18)C11—H110.95
C1—C81.4848 (17)C12—C131.3837 (19)
C1—C21.4895 (18)C12—H120.95
C2—C31.3957 (18)C13—H130.95
C2—C71.4007 (18)C14—C151.4196 (19)
C3—C41.3886 (18)C14—H140.95
C3—H30.95C15—C161.1987 (18)
C4—C51.386 (2)C16—C171.4324 (19)
C4—H40.95C17—C181.3994 (19)
C5—C61.387 (2)C17—C221.4023 (19)
C5—H50.95C18—C191.3805 (19)
C6—C71.3868 (19)C18—H180.95
C6—H60.95C19—C201.3841 (19)
C7—H70.95C19—H190.95
C8—C91.3971 (18)C20—C211.3843 (18)
C8—C131.3981 (18)C21—C221.3790 (18)
C9—C101.3881 (19)C21—H210.95
C9—H90.95C22—H220.95
O2—N1—O1123.39 (12)C12—C11—C10119.59 (13)
O2—N1—C20118.58 (11)C12—C11—H11120.2
O1—N1—C20118.03 (11)C10—C11—H11120.2
C14—C1—C8119.22 (12)C11—C12—C13120.49 (14)
C14—C1—C2121.54 (12)C11—C12—H12119.8
C8—C1—C2119.23 (11)C13—C12—H12119.8
C3—C2—C7118.37 (12)C12—C13—C8120.90 (13)
C3—C2—C1120.56 (11)C12—C13—H13119.5
C7—C2—C1121.05 (11)C8—C13—H13119.5
C4—C3—C2120.74 (12)C1—C14—C15125.33 (12)
C4—C3—H3119.6C1—C14—H14117.3
C2—C3—H3119.6C15—C14—H14117.3
C5—C4—C3120.25 (13)C16—C15—C14177.95 (15)
C5—C4—H4119.9C15—C16—C17174.26 (14)
C3—C4—H4119.9C18—C17—C22119.35 (12)
C4—C5—C6119.70 (12)C18—C17—C16119.07 (12)
C4—C5—H5120.2C22—C17—C16121.57 (12)
C6—C5—H5120.2C19—C18—C17120.36 (12)
C7—C6—C5120.19 (13)C19—C18—H18119.8
C7—C6—H6119.9C17—C18—H18119.8
C5—C6—H6119.9C18—C19—C20118.78 (13)
C6—C7—C2120.72 (12)C18—C19—H19120.6
C6—C7—H7119.6C20—C19—H19120.6
C2—C7—H7119.6C19—C20—C21122.38 (12)
C9—C8—C13117.83 (12)C19—C20—N1118.66 (12)
C9—C8—C1121.31 (12)C21—C20—N1118.95 (12)
C13—C8—C1120.85 (12)C22—C21—C20118.53 (12)
C10—C9—C8121.15 (13)C22—C21—H21120.7
C10—C9—H9119.4C20—C21—H21120.7
C8—C9—H9119.4C21—C22—C17120.59 (12)
C11—C10—C9119.99 (13)C21—C22—H22119.7
C11—C10—H10120.0C17—C22—H22119.7
C9—C10—H10120.0
C14—C1—C2—C3134.16 (14)C10—C11—C12—C131.6 (2)
C8—C1—C2—C345.48 (17)C11—C12—C13—C80.1 (2)
C14—C1—C2—C744.07 (18)C9—C8—C13—C122.0 (2)
C8—C1—C2—C7136.29 (13)C1—C8—C13—C12176.74 (13)
C7—C2—C3—C42.08 (19)C8—C1—C14—C15173.87 (12)
C1—C2—C3—C4176.19 (12)C2—C1—C14—C155.8 (2)
C2—C3—C4—C51.8 (2)C22—C17—C18—C190.79 (19)
C3—C4—C5—C60.1 (2)C16—C17—C18—C19178.70 (12)
C4—C5—C6—C71.3 (2)C17—C18—C19—C200.13 (19)
C5—C6—C7—C21.0 (2)C18—C19—C20—C210.8 (2)
C3—C2—C7—C60.72 (19)C18—C19—C20—N1178.43 (12)
C1—C2—C7—C6177.55 (12)O2—N1—C20—C19179.76 (12)
C14—C1—C8—C9149.19 (13)O1—N1—C20—C190.54 (18)
C2—C1—C8—C931.16 (18)O2—N1—C20—C211.00 (18)
C14—C1—C8—C1329.47 (18)O1—N1—C20—C21178.69 (12)
C2—C1—C8—C13150.18 (12)C19—C20—C21—C220.5 (2)
C13—C8—C9—C102.20 (19)N1—C20—C21—C22178.74 (12)
C1—C8—C9—C10176.50 (12)C20—C21—C22—C170.48 (19)
C8—C9—C10—C110.6 (2)C18—C17—C22—C211.10 (19)
C9—C10—C11—C121.4 (2)C16—C17—C22—C21178.38 (12)
Comparison of antibacterial activity of 1,3-enynes 1–3 against gram-positive and gram-negative bacteria, Candida and Aspergillus niger at a concentration of 50 µg ml-1 top
Microorganism123
Staphylococcus Aureus (G+)
Pseudomonas sp (G-)++
Escherichia coli (G-)++
Salmonella sp (G-)+
Candida sp.
Aspergillus niger++
Notes: (–) growth; (+) inhibition
 

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