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
CCDC references: 1894246; 1887111; 1882656
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)
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Crystal data top
C23H18 | F(000) = 624 |
Mr = 294.37 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 14.3054 (3) Å | Cell parameters from 5897 reflections |
b = 5.8354 (1) Å | θ = 3.8–68.2° |
c = 19.0365 (4) Å | µ = 0.52 mm−1 |
β = 90.935 (1)° | T = 100 K |
V = 1588.91 (5) Å3 | Block, clear light yellow |
Z = 4 | 0.25 × 0.15 × 0.10 mm |
Data collection top
Bruker D8 Venture diffractometer | 2897 independent reflections |
Radiation source: Incoatec Microsource | 2201 reflections with I > 2σ(I) |
Mirrors monochromator | Rint = 0.070 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 68.3°, θmin = 3.8° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −7→7 |
Tmin = 0.672, Tmax = 0.753 | l = −22→21 |
21068 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-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 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.62818 (12) | 0.4676 (3) | 0.34132 (9) | 0.0187 (4) | |
C2 | 0.52879 (12) | 0.5072 (3) | 0.32097 (9) | 0.0189 (4) | |
C3 | 0.50023 (12) | 0.7070 (3) | 0.28601 (10) | 0.0219 (4) | |
H3 | 0.5449 | 0.8224 | 0.2759 | 0.026* | |
C4 | 0.40756 (12) | 0.7384 (3) | 0.26599 (10) | 0.0237 (4) | |
H4 | 0.3894 | 0.8738 | 0.2416 | 0.028* | |
C5 | 0.34105 (12) | 0.5730 (3) | 0.28136 (9) | 0.0244 (4) | |
H5 | 0.2775 | 0.5948 | 0.2677 | 0.029* | |
C6 | 0.36825 (12) | 0.3761 (3) | 0.31683 (9) | 0.0228 (4) | |
H6 | 0.3229 | 0.2633 | 0.3279 | 0.027* | |
C7 | 0.46079 (12) | 0.3424 (3) | 0.33628 (9) | 0.0208 (4) | |
H7 | 0.4785 | 0.206 | 0.3603 | 0.025* | |
C8 | 0.64544 (11) | 0.3118 (3) | 0.40258 (9) | 0.0185 (4) | |
C9 | 0.60968 (12) | 0.3669 (3) | 0.46846 (9) | 0.0213 (4) | |
H9 | 0.5777 | 0.5079 | 0.4748 | 0.026* | |
C10 | 0.62064 (13) | 0.2171 (3) | 0.52448 (10) | 0.0243 (4) | |
H10 | 0.5964 | 0.2558 | 0.5691 | 0.029* | |
C11 | 0.66701 (13) | 0.0108 (3) | 0.51541 (10) | 0.0249 (4) | |
H11 | 0.6744 | −0.0921 | 0.5538 | 0.03* | |
C12 | 0.70260 (12) | −0.0454 (3) | 0.45040 (10) | 0.0236 (4) | |
H12 | 0.7343 | −0.1869 | 0.4442 | 0.028* | |
C13 | 0.69196 (12) | 0.1047 (3) | 0.39437 (10) | 0.0216 (4) | |
H13 | 0.7167 | 0.0656 | 0.3499 | 0.026* | |
C14 | 0.69851 (12) | 0.5676 (3) | 0.30626 (9) | 0.0196 (4) | |
H14 | 0.6826 | 0.6528 | 0.2653 | 0.024* | |
C15 | 0.79494 (12) | 0.5547 (3) | 0.32617 (9) | 0.0200 (4) | |
C16 | 0.87627 (12) | 0.5582 (3) | 0.34320 (9) | 0.0215 (4) | |
C17 | 0.97189 (12) | 0.5445 (3) | 0.36746 (9) | 0.0206 (4) | |
C18 | 0.99968 (12) | 0.3543 (3) | 0.40849 (9) | 0.0225 (4) | |
C19 | 1.09221 (13) | 0.3434 (3) | 0.43234 (10) | 0.0268 (4) | |
H19 | 1.1123 | 0.2158 | 0.4597 | 0.032* | |
C20 | 1.15554 (13) | 0.5157 (3) | 0.41682 (10) | 0.0270 (4) | |
H20 | 1.2181 | 0.5064 | 0.4341 | 0.032* | |
C21 | 1.12775 (13) | 0.7009 (3) | 0.37624 (10) | 0.0261 (4) | |
H21 | 1.1712 | 0.8184 | 0.3656 | 0.031* | |
C22 | 1.03653 (12) | 0.7149 (3) | 0.35113 (10) | 0.0230 (4) | |
H22 | 1.0179 | 0.841 | 0.3226 | 0.028* | |
C23 | 0.93035 (13) | 0.1711 (3) | 0.42587 (11) | 0.0276 (4) | |
H23A | 0.8993 | 0.1178 | 0.3826 | 0.041* | |
H23B | 0.8836 | 0.2333 | 0.4577 | 0.041* | |
H23C | 0.9628 | 0.0425 | 0.4486 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0219 (9) | 0.0155 (9) | 0.0189 (9) | 0.0004 (7) | 0.0019 (7) | −0.0036 (7) |
C2 | 0.0210 (9) | 0.0191 (9) | 0.0166 (9) | 0.0006 (7) | 0.0012 (7) | −0.0015 (7) |
C3 | 0.0211 (9) | 0.0208 (10) | 0.0237 (10) | −0.0006 (8) | 0.0030 (7) | 0.0012 (7) |
C4 | 0.0245 (9) | 0.0238 (10) | 0.0229 (10) | 0.0057 (8) | 0.0021 (8) | 0.0038 (8) |
C5 | 0.0199 (9) | 0.0326 (11) | 0.0208 (10) | 0.0021 (8) | −0.0006 (7) | 0.0004 (8) |
C6 | 0.0213 (9) | 0.0260 (10) | 0.0211 (10) | −0.0041 (8) | 0.0006 (7) | −0.0006 (8) |
C7 | 0.0237 (9) | 0.0200 (9) | 0.0186 (10) | −0.0003 (8) | −0.0003 (7) | 0.0000 (7) |
C8 | 0.0140 (8) | 0.0187 (9) | 0.0227 (10) | −0.0021 (7) | −0.0008 (7) | 0.0003 (7) |
C9 | 0.0184 (9) | 0.0216 (10) | 0.0239 (10) | 0.0009 (7) | 0.0009 (7) | −0.0016 (7) |
C10 | 0.0266 (10) | 0.0262 (10) | 0.0203 (10) | −0.0027 (8) | 0.0020 (7) | 0.0004 (8) |
C11 | 0.0263 (10) | 0.0247 (10) | 0.0235 (10) | −0.0025 (8) | −0.0016 (7) | 0.0068 (8) |
C12 | 0.0225 (9) | 0.0186 (10) | 0.0298 (11) | −0.0004 (8) | 0.0011 (8) | 0.0017 (8) |
C13 | 0.0208 (9) | 0.0201 (9) | 0.0238 (10) | −0.0002 (8) | 0.0031 (7) | −0.0004 (7) |
C14 | 0.0204 (9) | 0.0185 (9) | 0.0199 (10) | 0.0029 (7) | 0.0000 (7) | 0.0014 (7) |
C15 | 0.0229 (9) | 0.0179 (9) | 0.0195 (9) | 0.0017 (7) | 0.0043 (7) | 0.0006 (7) |
C16 | 0.0243 (10) | 0.0195 (9) | 0.0209 (10) | 0.0004 (8) | 0.0049 (7) | −0.0004 (7) |
C17 | 0.0199 (9) | 0.0222 (10) | 0.0199 (10) | 0.0003 (8) | 0.0028 (7) | −0.0043 (7) |
C18 | 0.0241 (9) | 0.0230 (10) | 0.0204 (10) | 0.0015 (8) | 0.0029 (7) | −0.0022 (8) |
C19 | 0.0244 (10) | 0.0300 (11) | 0.0258 (11) | 0.0033 (8) | −0.0015 (8) | 0.0015 (8) |
C20 | 0.0190 (9) | 0.0345 (12) | 0.0275 (11) | 0.0009 (8) | −0.0019 (8) | −0.0024 (9) |
C21 | 0.0208 (10) | 0.0289 (11) | 0.0286 (11) | −0.0040 (8) | 0.0034 (8) | −0.0034 (8) |
C22 | 0.0251 (10) | 0.0222 (10) | 0.0219 (10) | −0.0002 (8) | 0.0034 (8) | −0.0014 (8) |
C23 | 0.0262 (10) | 0.0250 (10) | 0.0316 (11) | −0.0005 (8) | 0.0026 (8) | 0.0044 (8) |
Geometric parameters (Å, º) top
C1—C14 | 1.349 (2) | C12—C13 | 1.387 (2) |
C1—C2 | 1.486 (2) | C12—H12 | 0.95 |
C1—C8 | 1.496 (2) | C13—H13 | 0.95 |
C2—C3 | 1.400 (2) | C14—C15 | 1.427 (2) |
C2—C7 | 1.402 (2) | C14—H14 | 0.95 |
C3—C4 | 1.385 (2) | C15—C16 | 1.203 (3) |
C3—H3 | 0.95 | C16—C17 | 1.439 (2) |
C4—C5 | 1.390 (3) | C17—C22 | 1.396 (2) |
C4—H4 | 0.95 | C17—C18 | 1.411 (3) |
C5—C6 | 1.385 (3) | C18—C19 | 1.394 (3) |
C5—H5 | 0.95 | C18—C23 | 1.499 (2) |
C6—C7 | 1.383 (2) | C19—C20 | 1.389 (3) |
C6—H6 | 0.95 | C19—H19 | 0.95 |
C7—H7 | 0.95 | C20—C21 | 1.383 (3) |
C8—C13 | 1.390 (2) | C20—H20 | 0.95 |
C8—C9 | 1.400 (2) | C21—C22 | 1.385 (2) |
C9—C10 | 1.386 (3) | C21—H21 | 0.95 |
C9—H9 | 0.95 | C22—H22 | 0.95 |
C10—C11 | 1.387 (3) | C23—H23A | 0.98 |
C10—H10 | 0.95 | C23—H23B | 0.98 |
C11—C12 | 1.385 (3) | C23—H23C | 0.98 |
C11—H11 | 0.95 | | |
| | | |
C14—C1—C2 | 121.47 (16) | C11—C12—H12 | 120.0 |
C14—C1—C8 | 122.24 (16) | C13—C12—H12 | 120.0 |
C2—C1—C8 | 116.29 (14) | C12—C13—C8 | 120.65 (17) |
C3—C2—C7 | 118.17 (16) | C12—C13—H13 | 119.7 |
C3—C2—C1 | 121.62 (16) | C8—C13—H13 | 119.7 |
C7—C2—C1 | 120.21 (16) | C1—C14—C15 | 124.86 (17) |
C4—C3—C2 | 120.76 (17) | C1—C14—H14 | 117.6 |
C4—C3—H3 | 119.6 | C15—C14—H14 | 117.6 |
C2—C3—H3 | 119.6 | C16—C15—C14 | 176.04 (19) |
C3—C4—C5 | 120.36 (17) | C15—C16—C17 | 174.8 (2) |
C3—C4—H4 | 119.8 | C22—C17—C18 | 120.12 (16) |
C5—C4—H4 | 119.8 | C22—C17—C16 | 121.25 (17) |
C6—C5—C4 | 119.40 (17) | C18—C17—C16 | 118.63 (16) |
C6—C5—H5 | 120.3 | C19—C18—C17 | 118.30 (17) |
C4—C5—H5 | 120.3 | C19—C18—C23 | 121.58 (17) |
C7—C6—C5 | 120.57 (17) | C17—C18—C23 | 120.12 (16) |
C7—C6—H6 | 119.7 | C20—C19—C18 | 121.12 (18) |
C5—C6—H6 | 119.7 | C20—C19—H19 | 119.4 |
C6—C7—C2 | 120.73 (17) | C18—C19—H19 | 119.4 |
C6—C7—H7 | 119.6 | C21—C20—C19 | 120.15 (17) |
C2—C7—H7 | 119.6 | C21—C20—H20 | 119.9 |
C13—C8—C9 | 118.90 (17) | C19—C20—H20 | 119.9 |
C13—C8—C1 | 120.94 (16) | C20—C21—C22 | 119.99 (18) |
C9—C8—C1 | 120.05 (15) | C20—C21—H21 | 120.0 |
C10—C9—C8 | 120.41 (17) | C22—C21—H21 | 120.0 |
C10—C9—H9 | 119.8 | C21—C22—C17 | 120.32 (18) |
C8—C9—H9 | 119.8 | C21—C22—H22 | 119.8 |
C9—C10—C11 | 120.01 (18) | C17—C22—H22 | 119.8 |
C9—C10—H10 | 120.0 | C18—C23—H23A | 109.5 |
C11—C10—H10 | 120.0 | C18—C23—H23B | 109.5 |
C12—C11—C10 | 120.02 (18) | H23A—C23—H23B | 109.5 |
C12—C11—H11 | 120.0 | C18—C23—H23C | 109.5 |
C10—C11—H11 | 120.0 | H23A—C23—H23C | 109.5 |
C11—C12—C13 | 120.01 (17) | H23B—C23—H23C | 109.5 |
| | | |
C14—C1—C2—C3 | −25.7 (3) | C9—C10—C11—C12 | 0.2 (3) |
C8—C1—C2—C3 | 154.24 (16) | C10—C11—C12—C13 | 0.1 (3) |
C14—C1—C2—C7 | 153.97 (17) | C11—C12—C13—C8 | −0.2 (3) |
C8—C1—C2—C7 | −26.1 (2) | C9—C8—C13—C12 | 0.2 (3) |
C7—C2—C3—C4 | −1.2 (3) | C1—C8—C13—C12 | −175.94 (16) |
C1—C2—C3—C4 | 178.46 (17) | C2—C1—C14—C15 | 174.16 (16) |
C2—C3—C4—C5 | 1.0 (3) | C8—C1—C14—C15 | −5.7 (3) |
C3—C4—C5—C6 | −0.1 (3) | C22—C17—C18—C19 | 0.6 (3) |
C4—C5—C6—C7 | −0.7 (3) | C16—C17—C18—C19 | −179.42 (17) |
C5—C6—C7—C2 | 0.5 (3) | C22—C17—C18—C23 | −179.84 (17) |
C3—C2—C7—C6 | 0.5 (3) | C16—C17—C18—C23 | 0.2 (3) |
C1—C2—C7—C6 | −179.20 (16) | C17—C18—C19—C20 | 0.6 (3) |
C14—C1—C8—C13 | −64.2 (2) | C23—C18—C19—C20 | −179.02 (18) |
C2—C1—C8—C13 | 115.94 (18) | C18—C19—C20—C21 | −0.9 (3) |
C14—C1—C8—C9 | 119.75 (19) | C19—C20—C21—C22 | 0.2 (3) |
C2—C1—C8—C9 | −60.2 (2) | C20—C21—C22—C17 | 1.0 (3) |
C13—C8—C9—C10 | 0.0 (3) | C18—C17—C22—C21 | −1.3 (3) |
C1—C8—C9—C10 | 176.20 (16) | C16—C17—C22—C21 | 178.64 (17) |
C8—C9—C10—C11 | −0.2 (3) | | |
4-(2-Methoxyphenyl)-1,1-diphenylbut-1-en-3-yne (JCP_07S)
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Crystal data top
C23H18O | Dx = 1.205 Mg m−3 |
Mr = 310.37 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pbca | Cell parameters from 9909 reflections |
a = 10.6325 (2) Å | θ = 4.1–68.3° |
b = 14.7734 (2) Å | µ = 0.56 mm−1 |
c = 21.7751 (4) Å | T = 100 K |
V = 3420.39 (10) Å3 | Block, clear light yellow |
Z = 8 | 0.45 × 0.35 × 0.25 mm |
F(000) = 1312 | |
Data collection top
Bruker D8 Venture diffractometer | 3129 independent reflections |
Radiation source: Incoatec Microsource | 2681 reflections with I > 2σ(I) |
Mirrors monochromator | Rint = 0.049 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 68.3°, θmin = 4.1° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −17→17 |
Tmin = 0.663, Tmax = 0.753 | l = −26→26 |
27165 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-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 reflections | Δρmax = 0.32 e Å−3 |
219 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015b) |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.81307 (10) | 0.58400 (7) | 0.40917 (5) | 0.0302 (3) | |
C1 | 0.35943 (14) | 0.36061 (9) | 0.40946 (6) | 0.0204 (3) | |
C2 | 0.32376 (13) | 0.27620 (10) | 0.44219 (7) | 0.0216 (3) | |
C3 | 0.25780 (14) | 0.20732 (10) | 0.41220 (8) | 0.0282 (4) | |
H3 | 0.2311 | 0.2156 | 0.3709 | 0.034* | |
C4 | 0.23109 (15) | 0.12685 (11) | 0.44246 (9) | 0.0369 (4) | |
H4 | 0.1874 | 0.08 | 0.4215 | 0.044* | |
C5 | 0.26775 (16) | 0.11423 (12) | 0.50312 (9) | 0.0397 (5) | |
H5 | 0.2496 | 0.0589 | 0.5236 | 0.048* | |
C6 | 0.33078 (16) | 0.18274 (12) | 0.53345 (8) | 0.0350 (4) | |
H6 | 0.3551 | 0.1747 | 0.5751 | 0.042* | |
C7 | 0.35865 (14) | 0.26295 (11) | 0.50356 (7) | 0.0271 (3) | |
H7 | 0.402 | 0.3096 | 0.5249 | 0.033* | |
C8 | 0.26657 (14) | 0.40265 (9) | 0.36748 (6) | 0.0204 (3) | |
C9 | 0.13830 (14) | 0.40071 (10) | 0.38151 (7) | 0.0250 (3) | |
H9 | 0.1102 | 0.3683 | 0.4166 | 0.03* | |
C10 | 0.05153 (16) | 0.44541 (11) | 0.34487 (8) | 0.0317 (4) | |
H10 | −0.0353 | 0.4436 | 0.3551 | 0.038* | |
C11 | 0.09088 (17) | 0.49242 (11) | 0.29361 (8) | 0.0358 (4) | |
H11 | 0.0317 | 0.5243 | 0.2691 | 0.043* | |
C12 | 0.21694 (17) | 0.49281 (12) | 0.27806 (7) | 0.0360 (4) | |
H12 | 0.2441 | 0.524 | 0.2423 | 0.043* | |
C13 | 0.30365 (16) | 0.44802 (11) | 0.31427 (7) | 0.0281 (4) | |
H13 | 0.3898 | 0.4481 | 0.3028 | 0.034* | |
C14 | 0.47479 (14) | 0.39614 (10) | 0.42026 (7) | 0.0237 (3) | |
H14 | 0.5276 | 0.3628 | 0.4472 | 0.028* | |
C15 | 0.52618 (14) | 0.47750 (10) | 0.39594 (7) | 0.0243 (3) | |
C16 | 0.57677 (14) | 0.54474 (10) | 0.37683 (7) | 0.0244 (3) | |
C17 | 0.63718 (15) | 0.62237 (10) | 0.35096 (7) | 0.0252 (3) | |
C18 | 0.76265 (16) | 0.64074 (10) | 0.36693 (7) | 0.0272 (4) | |
C19 | 0.82665 (17) | 0.71257 (12) | 0.33937 (8) | 0.0360 (4) | |
H19 | 0.9119 | 0.7245 | 0.3496 | 0.043* | |
C20 | 0.7645 (2) | 0.76611 (12) | 0.29700 (9) | 0.0429 (5) | |
H20 | 0.8083 | 0.8145 | 0.2778 | 0.051* | |
C21 | 0.64020 (18) | 0.75079 (12) | 0.28198 (8) | 0.0398 (4) | |
H21 | 0.5987 | 0.789 | 0.2533 | 0.048* | |
C22 | 0.57572 (17) | 0.67880 (11) | 0.30908 (7) | 0.0319 (4) | |
H22 | 0.49 | 0.6682 | 0.299 | 0.038* | |
C23 | 0.92553 (16) | 0.61278 (13) | 0.43930 (9) | 0.0396 (4) | |
H23A | 0.9948 | 0.6143 | 0.4096 | 0.059* | |
H23B | 0.946 | 0.5704 | 0.4724 | 0.059* | |
H23C | 0.913 | 0.6734 | 0.4565 | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0213 (6) | 0.0309 (6) | 0.0383 (6) | −0.0055 (5) | −0.0060 (5) | 0.0005 (5) |
C1 | 0.0194 (7) | 0.0196 (7) | 0.0221 (7) | 0.0009 (6) | 0.0013 (6) | −0.0032 (6) |
C2 | 0.0148 (7) | 0.0205 (7) | 0.0295 (7) | 0.0023 (6) | 0.0027 (6) | 0.0010 (6) |
C3 | 0.0199 (7) | 0.0235 (8) | 0.0412 (9) | 0.0004 (6) | −0.0014 (7) | −0.0006 (7) |
C4 | 0.0212 (8) | 0.0213 (8) | 0.0682 (12) | −0.0019 (7) | 0.0051 (8) | 0.0000 (8) |
C5 | 0.0249 (9) | 0.0290 (9) | 0.0651 (12) | 0.0082 (7) | 0.0166 (8) | 0.0193 (9) |
C6 | 0.0281 (9) | 0.0393 (10) | 0.0377 (9) | 0.0115 (8) | 0.0098 (7) | 0.0141 (8) |
C7 | 0.0222 (8) | 0.0299 (8) | 0.0293 (8) | 0.0046 (6) | 0.0040 (6) | 0.0021 (6) |
C8 | 0.0220 (7) | 0.0183 (7) | 0.0209 (7) | −0.0020 (6) | −0.0018 (6) | −0.0029 (6) |
C9 | 0.0229 (8) | 0.0234 (7) | 0.0285 (8) | −0.0012 (6) | −0.0016 (6) | 0.0018 (6) |
C10 | 0.0235 (8) | 0.0297 (8) | 0.0420 (9) | −0.0003 (7) | −0.0077 (7) | 0.0022 (7) |
C11 | 0.0358 (10) | 0.0322 (9) | 0.0393 (9) | −0.0031 (7) | −0.0173 (8) | 0.0068 (7) |
C12 | 0.0424 (11) | 0.0388 (10) | 0.0267 (8) | −0.0109 (8) | −0.0098 (7) | 0.0087 (7) |
C13 | 0.0286 (8) | 0.0326 (8) | 0.0230 (7) | −0.0074 (7) | −0.0023 (6) | −0.0006 (6) |
C14 | 0.0195 (7) | 0.0219 (7) | 0.0296 (8) | 0.0000 (6) | −0.0013 (6) | 0.0012 (6) |
C15 | 0.0174 (8) | 0.0254 (8) | 0.0301 (8) | −0.0002 (6) | −0.0009 (6) | −0.0021 (6) |
C16 | 0.0202 (7) | 0.0256 (8) | 0.0273 (7) | −0.0003 (6) | 0.0006 (6) | −0.0049 (6) |
C17 | 0.0252 (8) | 0.0230 (7) | 0.0275 (8) | −0.0017 (6) | 0.0039 (6) | −0.0051 (6) |
C18 | 0.0294 (8) | 0.0243 (8) | 0.0278 (7) | −0.0019 (6) | 0.0031 (7) | −0.0036 (6) |
C19 | 0.0316 (9) | 0.0341 (9) | 0.0424 (9) | −0.0092 (7) | 0.0062 (7) | −0.0043 (8) |
C20 | 0.0515 (12) | 0.0321 (9) | 0.0450 (10) | −0.0069 (9) | 0.0089 (9) | 0.0054 (8) |
C21 | 0.0470 (11) | 0.0333 (9) | 0.0391 (9) | 0.0017 (8) | 0.0011 (8) | 0.0071 (8) |
C22 | 0.0362 (9) | 0.0277 (8) | 0.0320 (8) | 0.0054 (7) | −0.0014 (7) | −0.0020 (7) |
C23 | 0.0254 (9) | 0.0441 (10) | 0.0493 (10) | −0.0057 (8) | −0.0095 (8) | −0.0023 (8) |
Geometric parameters (Å, º) top
O1—C18 | 1.3550 (19) | C11—C12 | 1.383 (3) |
O1—C23 | 1.4287 (19) | C11—H11 | 0.95 |
C1—C14 | 1.355 (2) | C12—C13 | 1.382 (2) |
C1—C8 | 1.482 (2) | C12—H12 | 0.95 |
C1—C2 | 1.485 (2) | C13—H13 | 0.95 |
C2—C3 | 1.398 (2) | C14—C15 | 1.423 (2) |
C2—C7 | 1.401 (2) | C14—H14 | 0.95 |
C3—C4 | 1.388 (2) | C15—C16 | 1.204 (2) |
C3—H3 | 0.95 | C16—C17 | 1.430 (2) |
C4—C5 | 1.390 (3) | C17—C22 | 1.398 (2) |
C4—H4 | 0.95 | C17—C18 | 1.405 (2) |
C5—C6 | 1.382 (3) | C18—C19 | 1.396 (2) |
C5—H5 | 0.95 | C19—C20 | 1.383 (3) |
C6—C7 | 1.384 (2) | C19—H19 | 0.95 |
C6—H6 | 0.95 | C20—C21 | 1.380 (3) |
C7—H7 | 0.95 | C20—H20 | 0.95 |
C8—C13 | 1.395 (2) | C21—C22 | 1.396 (2) |
C8—C9 | 1.398 (2) | C21—H21 | 0.95 |
C9—C10 | 1.387 (2) | C22—H22 | 0.95 |
C9—H9 | 0.95 | C23—H23A | 0.98 |
C10—C11 | 1.380 (2) | C23—H23B | 0.98 |
C10—H10 | 0.95 | C23—H23C | 0.98 |
| | | |
C18—O1—C23 | 117.30 (13) | C13—C12—H12 | 119.8 |
C14—C1—C8 | 123.22 (13) | C11—C12—H12 | 119.8 |
C14—C1—C2 | 118.24 (13) | C12—C13—C8 | 121.01 (15) |
C8—C1—C2 | 118.53 (12) | C12—C13—H13 | 119.5 |
C3—C2—C7 | 118.48 (14) | C8—C13—H13 | 119.5 |
C3—C2—C1 | 121.01 (13) | C1—C14—C15 | 127.63 (14) |
C7—C2—C1 | 120.49 (13) | C1—C14—H14 | 116.2 |
C4—C3—C2 | 120.28 (15) | C15—C14—H14 | 116.2 |
C4—C3—H3 | 119.9 | C16—C15—C14 | 175.94 (16) |
C2—C3—H3 | 119.9 | C15—C16—C17 | 176.93 (16) |
C3—C4—C5 | 120.57 (16) | C22—C17—C18 | 119.35 (15) |
C3—C4—H4 | 119.7 | C22—C17—C16 | 121.69 (15) |
C5—C4—H4 | 119.7 | C18—C17—C16 | 118.94 (14) |
C6—C5—C4 | 119.47 (15) | O1—C18—C19 | 124.69 (15) |
C6—C5—H5 | 120.3 | O1—C18—C17 | 115.10 (13) |
C4—C5—H5 | 120.3 | C19—C18—C17 | 120.21 (15) |
C5—C6—C7 | 120.42 (16) | C20—C19—C18 | 119.24 (17) |
C5—C6—H6 | 119.8 | C20—C19—H19 | 120.4 |
C7—C6—H6 | 119.8 | C18—C19—H19 | 120.4 |
C6—C7—C2 | 120.76 (16) | C21—C20—C19 | 121.44 (17) |
C6—C7—H7 | 119.6 | C21—C20—H20 | 119.3 |
C2—C7—H7 | 119.6 | C19—C20—H20 | 119.3 |
C13—C8—C9 | 117.84 (14) | C20—C21—C22 | 119.67 (17) |
C13—C8—C1 | 121.68 (14) | C20—C21—H21 | 120.2 |
C9—C8—C1 | 120.43 (13) | C22—C21—H21 | 120.2 |
C10—C9—C8 | 120.89 (14) | C21—C22—C17 | 120.03 (17) |
C10—C9—H9 | 119.6 | C21—C22—H22 | 120.0 |
C8—C9—H9 | 119.6 | C17—C22—H22 | 120.0 |
C11—C10—C9 | 120.22 (16) | O1—C23—H23A | 109.5 |
C11—C10—H10 | 119.9 | O1—C23—H23B | 109.5 |
C9—C10—H10 | 119.9 | H23A—C23—H23B | 109.5 |
C10—C11—C12 | 119.62 (15) | O1—C23—H23C | 109.5 |
C10—C11—H11 | 120.2 | H23A—C23—H23C | 109.5 |
C12—C11—H11 | 120.2 | H23B—C23—H23C | 109.5 |
C13—C12—C11 | 120.34 (15) | | |
| | | |
C14—C1—C2—C3 | −139.45 (15) | C10—C11—C12—C13 | −1.4 (3) |
C8—C1—C2—C3 | 41.58 (19) | C11—C12—C13—C8 | −0.9 (3) |
C14—C1—C2—C7 | 38.8 (2) | C9—C8—C13—C12 | 2.7 (2) |
C8—C1—C2—C7 | −140.15 (14) | C1—C8—C13—C12 | −174.99 (14) |
C7—C2—C3—C4 | −1.8 (2) | C8—C1—C14—C15 | 1.5 (2) |
C1—C2—C3—C4 | 176.53 (14) | C2—C1—C14—C15 | −177.46 (14) |
C2—C3—C4—C5 | 1.0 (2) | C23—O1—C18—C19 | 17.2 (2) |
C3—C4—C5—C6 | 0.3 (2) | C23—O1—C18—C17 | −163.43 (14) |
C4—C5—C6—C7 | −0.8 (2) | C22—C17—C18—O1 | 178.13 (13) |
C5—C6—C7—C2 | −0.1 (2) | C16—C17—C18—O1 | −3.5 (2) |
C3—C2—C7—C6 | 1.3 (2) | C22—C17—C18—C19 | −2.5 (2) |
C1—C2—C7—C6 | −176.99 (13) | C16—C17—C18—C19 | 175.83 (15) |
C14—C1—C8—C13 | 34.7 (2) | O1—C18—C19—C20 | −179.67 (15) |
C2—C1—C8—C13 | −146.42 (14) | C17—C18—C19—C20 | 1.0 (2) |
C14—C1—C8—C9 | −142.96 (15) | C18—C19—C20—C21 | 0.8 (3) |
C2—C1—C8—C9 | 35.97 (19) | C19—C20—C21—C22 | −1.2 (3) |
C13—C8—C9—C10 | −2.4 (2) | C20—C21—C22—C17 | −0.3 (3) |
C1—C8—C9—C10 | 175.33 (14) | C18—C17—C22—C21 | 2.1 (2) |
C8—C9—C10—C11 | 0.2 (2) | C16—C17—C22—C21 | −176.13 (15) |
C9—C10—C11—C12 | 1.7 (3) | | |
4-(4-Nitrophenyl)-1,1-diphenylbut-1-en-3-yne (JCP_10S)
top
Crystal data top
C22H15NO2 | F(000) = 680 |
Mr = 325.36 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6548 (5) Å | Cell parameters from 9866 reflections |
b = 22.2107 (10) Å | θ = 2.8–27.5° |
c = 7.9248 (4) Å | µ = 0.09 mm−1 |
β = 105.749 (1)° | T = 100 K |
V = 1635.60 (14) Å3 | Block, clear pale yellow |
Z = 4 | 0.35 × 0.25 × 0.15 mm |
Data collection top
Bruker D8 Venture diffractometer | 3763 independent reflections |
Radiation source: Incoatec Microsource | 2822 reflections with I > 2σ(I) |
Mirrors monochromator | Rint = 0.046 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 27.5°, θmin = 2.8° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | k = −28→28 |
Tmin = 0.717, Tmax = 0.746 | l = −10→10 |
40247 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-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 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.06547 (11) | 0.57359 (5) | 1.24915 (14) | 0.0290 (3) | |
O2 | 0.96091 (10) | 0.66032 (4) | 1.23968 (13) | 0.0261 (2) | |
N1 | 0.96049 (12) | 0.60708 (5) | 1.19807 (15) | 0.0205 (3) | |
C1 | 0.23501 (14) | 0.39605 (6) | 0.47305 (16) | 0.0155 (3) | |
C2 | 0.35549 (14) | 0.35375 (6) | 0.54916 (16) | 0.0157 (3) | |
C3 | 0.32967 (14) | 0.29915 (6) | 0.62236 (17) | 0.0181 (3) | |
H3 | 0.2337 | 0.2878 | 0.6172 | 0.022* | |
C4 | 0.44266 (15) | 0.26120 (6) | 0.70263 (18) | 0.0209 (3) | |
H4 | 0.4238 | 0.2247 | 0.7548 | 0.025* | |
C5 | 0.58279 (15) | 0.27639 (6) | 0.70686 (18) | 0.0215 (3) | |
H5 | 0.66 | 0.2504 | 0.7617 | 0.026* | |
C6 | 0.60984 (15) | 0.32977 (6) | 0.63058 (18) | 0.0214 (3) | |
H6 | 0.7055 | 0.3399 | 0.6311 | 0.026* | |
C7 | 0.49756 (14) | 0.36836 (6) | 0.55356 (17) | 0.0181 (3) | |
H7 | 0.5172 | 0.4051 | 0.5032 | 0.022* | |
C8 | 0.09902 (14) | 0.37215 (6) | 0.35605 (16) | 0.0161 (3) | |
C9 | 0.09857 (15) | 0.32199 (6) | 0.24950 (17) | 0.0197 (3) | |
H9 | 0.1862 | 0.3014 | 0.2566 | 0.024* | |
C10 | −0.02771 (16) | 0.30173 (6) | 0.13340 (18) | 0.0244 (3) | |
H10 | −0.0259 | 0.2678 | 0.0612 | 0.029* | |
C11 | −0.15640 (15) | 0.33103 (7) | 0.12283 (18) | 0.0248 (3) | |
H11 | −0.2427 | 0.3178 | 0.0417 | 0.03* | |
C12 | −0.15856 (15) | 0.37963 (7) | 0.23106 (19) | 0.0257 (3) | |
H12 | −0.2471 | 0.3992 | 0.2262 | 0.031* | |
C13 | −0.03271 (14) | 0.40003 (6) | 0.34644 (18) | 0.0212 (3) | |
H13 | −0.0359 | 0.4335 | 0.4201 | 0.025* | |
C14 | 0.24632 (14) | 0.45581 (6) | 0.50884 (17) | 0.0181 (3) | |
H14 | 0.1693 | 0.4809 | 0.4476 | 0.022* | |
C15 | 0.36393 (15) | 0.48402 (6) | 0.63032 (17) | 0.0179 (3) | |
C16 | 0.46033 (14) | 0.50917 (6) | 0.73385 (17) | 0.0188 (3) | |
C17 | 0.58479 (14) | 0.53456 (6) | 0.85444 (17) | 0.0177 (3) | |
C18 | 0.70564 (15) | 0.49816 (6) | 0.92069 (17) | 0.0203 (3) | |
H18 | 0.7034 | 0.457 | 0.8873 | 0.024* | |
C19 | 0.82814 (15) | 0.52171 (6) | 1.03438 (18) | 0.0200 (3) | |
H19 | 0.9103 | 0.4971 | 1.0798 | 0.024* | |
C20 | 0.82900 (14) | 0.58180 (6) | 1.08093 (16) | 0.0177 (3) | |
C21 | 0.71092 (14) | 0.61893 (6) | 1.01923 (17) | 0.0183 (3) | |
H21 | 0.714 | 0.66 | 1.0539 | 0.022* | |
C22 | 0.58867 (14) | 0.59503 (6) | 0.90637 (17) | 0.0189 (3) | |
H22 | 0.5063 | 0.6198 | 0.8634 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0190 (5) | 0.0322 (6) | 0.0321 (6) | 0.0051 (4) | 0.0007 (4) | −0.0011 (5) |
O2 | 0.0254 (6) | 0.0215 (5) | 0.0292 (6) | −0.0034 (4) | 0.0034 (4) | −0.0060 (4) |
N1 | 0.0180 (6) | 0.0243 (6) | 0.0194 (6) | −0.0004 (5) | 0.0052 (5) | 0.0011 (5) |
C1 | 0.0159 (7) | 0.0172 (7) | 0.0138 (6) | −0.0001 (5) | 0.0048 (5) | 0.0012 (5) |
C2 | 0.0177 (7) | 0.0148 (6) | 0.0139 (6) | 0.0003 (5) | 0.0031 (5) | −0.0028 (5) |
C3 | 0.0173 (7) | 0.0167 (7) | 0.0203 (7) | −0.0009 (5) | 0.0051 (5) | −0.0016 (5) |
C4 | 0.0249 (8) | 0.0160 (7) | 0.0208 (7) | 0.0013 (6) | 0.0048 (6) | 0.0006 (5) |
C5 | 0.0194 (7) | 0.0202 (7) | 0.0211 (7) | 0.0064 (6) | −0.0009 (6) | −0.0024 (6) |
C6 | 0.0151 (7) | 0.0246 (7) | 0.0232 (7) | −0.0011 (6) | 0.0030 (6) | −0.0053 (6) |
C7 | 0.0201 (7) | 0.0161 (6) | 0.0176 (6) | −0.0031 (5) | 0.0045 (5) | −0.0022 (5) |
C8 | 0.0170 (7) | 0.0153 (6) | 0.0149 (6) | −0.0001 (5) | 0.0025 (5) | 0.0029 (5) |
C9 | 0.0189 (7) | 0.0191 (7) | 0.0205 (7) | 0.0000 (5) | 0.0043 (5) | −0.0011 (5) |
C10 | 0.0296 (8) | 0.0208 (7) | 0.0210 (7) | −0.0039 (6) | 0.0036 (6) | −0.0018 (6) |
C11 | 0.0213 (8) | 0.0260 (8) | 0.0219 (7) | −0.0068 (6) | −0.0030 (6) | 0.0034 (6) |
C12 | 0.0170 (7) | 0.0277 (8) | 0.0296 (8) | 0.0028 (6) | 0.0017 (6) | 0.0036 (6) |
C13 | 0.0209 (7) | 0.0193 (7) | 0.0224 (7) | 0.0016 (6) | 0.0043 (6) | −0.0006 (6) |
C14 | 0.0184 (7) | 0.0178 (7) | 0.0172 (6) | 0.0010 (5) | 0.0034 (5) | 0.0013 (5) |
C15 | 0.0226 (7) | 0.0129 (6) | 0.0193 (6) | 0.0006 (5) | 0.0074 (6) | 0.0011 (5) |
C16 | 0.0237 (7) | 0.0141 (6) | 0.0202 (7) | −0.0004 (5) | 0.0085 (6) | −0.0001 (5) |
C17 | 0.0213 (7) | 0.0182 (7) | 0.0155 (6) | −0.0039 (6) | 0.0081 (5) | −0.0005 (5) |
C18 | 0.0248 (8) | 0.0150 (6) | 0.0230 (7) | −0.0005 (6) | 0.0097 (6) | −0.0009 (5) |
C19 | 0.0191 (7) | 0.0200 (7) | 0.0221 (7) | 0.0030 (5) | 0.0078 (5) | 0.0019 (6) |
C20 | 0.0175 (7) | 0.0213 (7) | 0.0150 (6) | −0.0030 (5) | 0.0057 (5) | 0.0001 (5) |
C21 | 0.0211 (7) | 0.0152 (6) | 0.0187 (6) | −0.0007 (5) | 0.0055 (5) | −0.0008 (5) |
C22 | 0.0194 (7) | 0.0175 (7) | 0.0198 (7) | 0.0015 (5) | 0.0050 (5) | 0.0008 (5) |
Geometric parameters (Å, º) top
O1—N1 | 1.2336 (14) | C10—C11 | 1.385 (2) |
O2—N1 | 1.2273 (15) | C10—H10 | 0.95 |
N1—C20 | 1.4659 (17) | C11—C12 | 1.382 (2) |
C1—C14 | 1.3554 (18) | C11—H11 | 0.95 |
C1—C8 | 1.4848 (17) | C12—C13 | 1.3837 (19) |
C1—C2 | 1.4895 (18) | C12—H12 | 0.95 |
C2—C3 | 1.3957 (18) | C13—H13 | 0.95 |
C2—C7 | 1.4007 (18) | C14—C15 | 1.4196 (19) |
C3—C4 | 1.3886 (18) | C14—H14 | 0.95 |
C3—H3 | 0.95 | C15—C16 | 1.1987 (18) |
C4—C5 | 1.386 (2) | C16—C17 | 1.4324 (19) |
C4—H4 | 0.95 | C17—C18 | 1.3994 (19) |
C5—C6 | 1.387 (2) | C17—C22 | 1.4023 (19) |
C5—H5 | 0.95 | C18—C19 | 1.3805 (19) |
C6—C7 | 1.3868 (19) | C18—H18 | 0.95 |
C6—H6 | 0.95 | C19—C20 | 1.3841 (19) |
C7—H7 | 0.95 | C19—H19 | 0.95 |
C8—C9 | 1.3971 (18) | C20—C21 | 1.3843 (18) |
C8—C13 | 1.3981 (18) | C21—C22 | 1.3790 (18) |
C9—C10 | 1.3881 (19) | C21—H21 | 0.95 |
C9—H9 | 0.95 | C22—H22 | 0.95 |
| | | |
O2—N1—O1 | 123.39 (12) | C12—C11—C10 | 119.59 (13) |
O2—N1—C20 | 118.58 (11) | C12—C11—H11 | 120.2 |
O1—N1—C20 | 118.03 (11) | C10—C11—H11 | 120.2 |
C14—C1—C8 | 119.22 (12) | C11—C12—C13 | 120.49 (14) |
C14—C1—C2 | 121.54 (12) | C11—C12—H12 | 119.8 |
C8—C1—C2 | 119.23 (11) | C13—C12—H12 | 119.8 |
C3—C2—C7 | 118.37 (12) | C12—C13—C8 | 120.90 (13) |
C3—C2—C1 | 120.56 (11) | C12—C13—H13 | 119.5 |
C7—C2—C1 | 121.05 (11) | C8—C13—H13 | 119.5 |
C4—C3—C2 | 120.74 (12) | C1—C14—C15 | 125.33 (12) |
C4—C3—H3 | 119.6 | C1—C14—H14 | 117.3 |
C2—C3—H3 | 119.6 | C15—C14—H14 | 117.3 |
C5—C4—C3 | 120.25 (13) | C16—C15—C14 | 177.95 (15) |
C5—C4—H4 | 119.9 | C15—C16—C17 | 174.26 (14) |
C3—C4—H4 | 119.9 | C18—C17—C22 | 119.35 (12) |
C4—C5—C6 | 119.70 (12) | C18—C17—C16 | 119.07 (12) |
C4—C5—H5 | 120.2 | C22—C17—C16 | 121.57 (12) |
C6—C5—H5 | 120.2 | C19—C18—C17 | 120.36 (12) |
C7—C6—C5 | 120.19 (13) | C19—C18—H18 | 119.8 |
C7—C6—H6 | 119.9 | C17—C18—H18 | 119.8 |
C5—C6—H6 | 119.9 | C18—C19—C20 | 118.78 (13) |
C6—C7—C2 | 120.72 (12) | C18—C19—H19 | 120.6 |
C6—C7—H7 | 119.6 | C20—C19—H19 | 120.6 |
C2—C7—H7 | 119.6 | C19—C20—C21 | 122.38 (12) |
C9—C8—C13 | 117.83 (12) | C19—C20—N1 | 118.66 (12) |
C9—C8—C1 | 121.31 (12) | C21—C20—N1 | 118.95 (12) |
C13—C8—C1 | 120.85 (12) | C22—C21—C20 | 118.53 (12) |
C10—C9—C8 | 121.15 (13) | C22—C21—H21 | 120.7 |
C10—C9—H9 | 119.4 | C20—C21—H21 | 120.7 |
C8—C9—H9 | 119.4 | C21—C22—C17 | 120.59 (12) |
C11—C10—C9 | 119.99 (13) | C21—C22—H22 | 119.7 |
C11—C10—H10 | 120.0 | C17—C22—H22 | 119.7 |
C9—C10—H10 | 120.0 | | |
| | | |
C14—C1—C2—C3 | 134.16 (14) | C10—C11—C12—C13 | 1.6 (2) |
C8—C1—C2—C3 | −45.48 (17) | C11—C12—C13—C8 | 0.1 (2) |
C14—C1—C2—C7 | −44.07 (18) | C9—C8—C13—C12 | −2.0 (2) |
C8—C1—C2—C7 | 136.29 (13) | C1—C8—C13—C12 | 176.74 (13) |
C7—C2—C3—C4 | 2.08 (19) | C8—C1—C14—C15 | 173.87 (12) |
C1—C2—C3—C4 | −176.19 (12) | C2—C1—C14—C15 | −5.8 (2) |
C2—C3—C4—C5 | −1.8 (2) | C22—C17—C18—C19 | −0.79 (19) |
C3—C4—C5—C6 | 0.1 (2) | C16—C17—C18—C19 | 178.70 (12) |
C4—C5—C6—C7 | 1.3 (2) | C17—C18—C19—C20 | −0.13 (19) |
C5—C6—C7—C2 | −1.0 (2) | C18—C19—C20—C21 | 0.8 (2) |
C3—C2—C7—C6 | −0.72 (19) | C18—C19—C20—N1 | −178.43 (12) |
C1—C2—C7—C6 | 177.55 (12) | O2—N1—C20—C19 | −179.76 (12) |
C14—C1—C8—C9 | 149.19 (13) | O1—N1—C20—C19 | 0.54 (18) |
C2—C1—C8—C9 | −31.16 (18) | O2—N1—C20—C21 | 1.00 (18) |
C14—C1—C8—C13 | −29.47 (18) | O1—N1—C20—C21 | −178.69 (12) |
C2—C1—C8—C13 | 150.18 (12) | C19—C20—C21—C22 | −0.5 (2) |
C13—C8—C9—C10 | 2.20 (19) | N1—C20—C21—C22 | 178.74 (12) |
C1—C8—C9—C10 | −176.50 (12) | C20—C21—C22—C17 | −0.48 (19) |
C8—C9—C10—C11 | −0.6 (2) | C18—C17—C22—C21 | 1.10 (19) |
C9—C10—C11—C12 | −1.4 (2) | C16—C17—C22—C21 | −178.38 (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 topMicroorganism | 1 | 2 | 3 |
Staphylococcus Aureus (G+) | – | – | – |
Pseudomonas sp (G-) | – | + | + |
Escherichia coli (G-) | – | + | + |
Salmonella sp (G-) | – | – | + |
Candida sp. | – | – | – |
Aspergillus niger | – | ++ | – |
Notes: (–) growth; (+) inhibition |