organic compounds
(E)-2-Phenyl-N-tosylnon-2-en-4-ynamide
aDepartment of Chemistry and Life Science, Chaohu College, Anhui Province, People's Republic of China
*Correspondence e-mail: wzys2012@126.com
The molecule of the title compound, C22H23NO3S, adopts an E conformation about the C=C bond. The dihedral angle between the benzene rings is 23.79 (5)°. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules, forming inversion dimers. The terminal butyl group is disordered over two sets of sites in a 0.559 (6):0.441 (6) ratio.
Related literature
For the synthesis of the titlw compound, see: Cheng et al. (2012). For applications of conjugated enynes, see: Ochiai et al. (1999); Saito et al. (2001).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S1600536812048489/xu5655sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812048489/xu5655Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812048489/xu5655Isup3.cml
The compound was prepared according to the reference (Cheng et al., 2012). 4-Methylbenzenesulfonyl azide (0.45 mmol), CuI (5.7 mg, 0.03 mmol), ethynylbenzene (0.45 mmol), and hept-2-ynal (0.3 mmol) were suspended in THF in a 10 ml Schlenk tube at room temperature at N2 atmosphere. Cs2CO3 (8.64 mg, 0.36 mmol) was then added, and the resulting solution was stirred at this temperature for 24 h. The reaction was quenched by saturated aqueous NH4Cl (5 ml) and extracted with CH2Cl2 (15 ml × 3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by
on silica gel (n-hexane/EtOAc) to afford the title compound. The title compound was recrystallized from CH2Cl2 at room temperature to give the desired crystals suitable for single-crystal X-ray diffraction.H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with aromatic C—H = 0.93–0.97 Å and N—H = 0.86 Å, Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) for the others. The butyl group is disordered over two positions, site occupancies were refined.
Conjugated enynes can be used in the synthesis of polymers (Ochiai et al., 1999) and in the selective construction of aromatic frameworks (Saito et al., 2001). Here, we report the
of the title enyne compound.The molecular structure of the title compound is shown in Figure 1, the ORTEP diagram shows that the structure adopts the E isomer, the double bond and triple bond are within normal ranges. The benzene C2–C7 and C10–C15 rings are tilted relative to each other by 23.79 (5)°. The chain C19—C22 is disorder. A view of the crystal packing for the title compound is illustrated in Fig. 2, the
is stabilized by N—H···O hydrogen bonds.For the synthesis of the titlw compound, see: Cheng et al. (2012). For applications of conjugated enynes, see: Ochiai et al. (1999); Saito et al. (2001).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the compound with displacement ellipsoids drawn at 30% probability level. | |
Fig. 2. The crystal packing diagram. |
C22H23NO3S | Z = 2 |
Mr = 381.47 | F(000) = 404 |
Triclinic, P1 | Dx = 1.240 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.8186 (10) Å | Cell parameters from 2435 reflections |
b = 9.8201 (9) Å | θ = 2.9–29.6° |
c = 11.3352 (13) Å | µ = 0.18 mm−1 |
α = 81.470 (8)° | T = 293 K |
β = 76.308 (9)° | Block, colorless |
γ = 75.042 (9)° | 0.42 × 0.38 × 0.32 mm |
V = 1021.46 (18) Å3 |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 4425 independent reflections |
Radiation source: fine-focus sealed tube | 3005 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.3592 pixels mm-1 | θmax = 27.1°, θmin = 2.9° |
ω scans | h = −12→11 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | k = −12→12 |
Tmin = 0.928, Tmax = 0.945 | l = −14→13 |
9118 measured reflections |
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)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0145P)2 + 0.450P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
4425 reflections | Δρmax = 0.19 e Å−3 |
285 parameters | Δρmin = −0.28 e Å−3 |
170 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0511 (16) |
C22H23NO3S | γ = 75.042 (9)° |
Mr = 381.47 | V = 1021.46 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8186 (10) Å | Mo Kα radiation |
b = 9.8201 (9) Å | µ = 0.18 mm−1 |
c = 11.3352 (13) Å | T = 293 K |
α = 81.470 (8)° | 0.42 × 0.38 × 0.32 mm |
β = 76.308 (9)° |
Agilent Xcalibur (Atlas, Gemini ultra) diffractometer | 4425 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | 3005 reflections with I > 2σ(I) |
Tmin = 0.928, Tmax = 0.945 | Rint = 0.028 |
9118 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 170 restraints |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.19 e Å−3 |
4425 reflections | Δρmin = −0.28 e Å−3 |
285 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.49748 (6) | 0.27503 (5) | 0.07181 (5) | 0.04966 (17) | |
O1 | 0.56428 (17) | 0.13893 (14) | 0.11958 (14) | 0.0656 (4) | |
O2 | 0.58196 (15) | 0.35117 (14) | −0.02248 (13) | 0.0575 (4) | |
O3 | 0.3159 (2) | 0.23691 (16) | 0.31525 (14) | 0.0779 (5) | |
N1 | 0.43740 (19) | 0.38162 (16) | 0.18182 (15) | 0.0518 (5) | |
H1 | 0.4617 | 0.4614 | 0.1702 | 0.062* | |
C1 | −0.0183 (3) | 0.2430 (4) | −0.1135 (4) | 0.1257 (13) | |
H1A | −0.1011 | 0.2483 | −0.0478 | 0.189* | |
H1B | 0.0011 | 0.1555 | −0.1495 | 0.189* | |
H1C | −0.0368 | 0.3210 | −0.1741 | 0.189* | |
C2 | 0.2639 (3) | 0.3857 (2) | −0.0279 (2) | 0.0631 (6) | |
H2 | 0.2878 | 0.4724 | −0.0331 | 0.076* | |
C3 | 0.1480 (3) | 0.3764 (3) | −0.0711 (2) | 0.0757 (7) | |
H3 | 0.0932 | 0.4579 | −0.1053 | 0.091* | |
C4 | 0.1106 (3) | 0.2494 (3) | −0.0651 (2) | 0.0753 (8) | |
C5 | 0.1929 (3) | 0.1314 (3) | −0.0146 (3) | 0.0774 (8) | |
H5 | 0.1695 | 0.0446 | −0.0105 | 0.093* | |
C6 | 0.3097 (3) | 0.1372 (2) | 0.0305 (2) | 0.0608 (6) | |
H6 | 0.3638 | 0.0557 | 0.0652 | 0.073* | |
C7 | 0.3449 (2) | 0.26491 (19) | 0.02339 (17) | 0.0464 (5) | |
C8 | 0.3496 (2) | 0.3491 (2) | 0.29221 (19) | 0.0529 (5) | |
C9 | 0.3001 (2) | 0.4641 (2) | 0.37598 (18) | 0.0483 (5) | |
C10 | 0.3535 (2) | 0.5957 (2) | 0.34604 (17) | 0.0461 (5) | |
C11 | 0.2602 (3) | 0.7245 (2) | 0.3255 (2) | 0.0645 (6) | |
H11 | 0.1639 | 0.7281 | 0.3285 | 0.077* | |
C12 | 0.3082 (4) | 0.8474 (3) | 0.3008 (2) | 0.0830 (9) | |
H12 | 0.2442 | 0.9333 | 0.2871 | 0.100* | |
C13 | 0.4484 (4) | 0.8444 (3) | 0.2964 (2) | 0.0825 (9) | |
H13 | 0.4803 | 0.9278 | 0.2790 | 0.099* | |
C14 | 0.5422 (3) | 0.7185 (3) | 0.3175 (2) | 0.0743 (7) | |
H14 | 0.6379 | 0.7163 | 0.3158 | 0.089* | |
C15 | 0.4949 (3) | 0.5942 (2) | 0.3415 (2) | 0.0576 (6) | |
H15 | 0.5597 | 0.5086 | 0.3547 | 0.069* | |
C16 | 0.2024 (3) | 0.4427 (2) | 0.4767 (2) | 0.0615 (6) | |
H16 | 0.1715 | 0.3588 | 0.4888 | 0.074* | |
C17 | 0.1426 (3) | 0.5407 (3) | 0.5667 (2) | 0.0658 (7) | |
C18 | 0.0934 (3) | 0.6244 (3) | 0.6390 (2) | 0.0734 (7) | |
C19 | 0.0400 (14) | 0.7233 (10) | 0.7344 (10) | 0.096 (4) | 0.559 (6) |
H19A | 0.0823 | 0.6839 | 0.8048 | 0.115* | 0.559 (6) |
H19B | −0.0639 | 0.7386 | 0.7600 | 0.115* | 0.559 (6) |
C20 | 0.0816 (6) | 0.8656 (7) | 0.6826 (7) | 0.099 (2) | 0.559 (6) |
H20A | 0.0368 | 0.9339 | 0.7422 | 0.119* | 0.559 (6) |
H20B | 0.0427 | 0.9008 | 0.6100 | 0.119* | 0.559 (6) |
C21 | 0.2508 (6) | 0.8559 (7) | 0.6491 (7) | 0.0798 (19) | 0.559 (6) |
H21A | 0.2915 | 0.8123 | 0.7195 | 0.096* | 0.559 (6) |
H21B | 0.2945 | 0.7949 | 0.5837 | 0.096* | 0.559 (6) |
C22 | 0.2860 (10) | 0.9846 (8) | 0.6137 (9) | 0.121 (3) | 0.559 (6) |
H22A | 0.3887 | 0.9717 | 0.5986 | 0.181* | 0.559 (6) |
H22B | 0.2416 | 1.0465 | 0.6772 | 0.181* | 0.559 (6) |
H22C | 0.2521 | 1.0257 | 0.5406 | 0.181* | 0.559 (6) |
C19A | 0.0304 (13) | 0.7466 (14) | 0.7125 (13) | 0.084 (3) | 0.441 (6) |
H19C | −0.0326 | 0.7186 | 0.7869 | 0.101* | 0.441 (6) |
H19D | −0.0269 | 0.8220 | 0.6670 | 0.101* | 0.441 (6) |
C20A | 0.1514 (10) | 0.8022 (9) | 0.7455 (6) | 0.096 (2) | 0.441 (6) |
H20C | 0.2342 | 0.7266 | 0.7574 | 0.115* | 0.441 (6) |
H20D | 0.1162 | 0.8556 | 0.8164 | 0.115* | 0.441 (6) |
C21A | 0.1841 (16) | 0.8992 (12) | 0.6240 (9) | 0.124 (3) | 0.441 (6) |
H21C | 0.2709 | 0.8427 | 0.5777 | 0.149* | 0.441 (6) |
H21D | 0.1080 | 0.8986 | 0.5831 | 0.149* | 0.441 (6) |
C22A | 0.2024 (16) | 1.0297 (11) | 0.5965 (14) | 0.160 (5) | 0.441 (6) |
H22D | 0.2938 | 1.0283 | 0.5419 | 0.239* | 0.441 (6) |
H22E | 0.2000 | 1.0693 | 0.6697 | 0.239* | 0.441 (6) |
H22F | 0.1266 | 1.0864 | 0.5580 | 0.239* | 0.441 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0597 (3) | 0.0411 (3) | 0.0472 (3) | −0.0092 (2) | −0.0053 (3) | −0.0148 (2) |
O1 | 0.0807 (11) | 0.0439 (8) | 0.0695 (11) | 0.0011 (7) | −0.0232 (9) | −0.0118 (7) |
O2 | 0.0599 (9) | 0.0561 (8) | 0.0546 (9) | −0.0175 (7) | 0.0046 (7) | −0.0182 (7) |
O3 | 0.1151 (15) | 0.0594 (9) | 0.0603 (10) | −0.0392 (10) | 0.0058 (10) | −0.0144 (8) |
N1 | 0.0683 (12) | 0.0441 (9) | 0.0449 (10) | −0.0186 (8) | −0.0025 (9) | −0.0154 (8) |
C1 | 0.081 (2) | 0.166 (3) | 0.153 (3) | −0.021 (2) | −0.040 (2) | −0.074 (3) |
C2 | 0.0676 (16) | 0.0556 (13) | 0.0668 (16) | −0.0143 (12) | −0.0147 (13) | −0.0064 (11) |
C3 | 0.0676 (17) | 0.0838 (18) | 0.0725 (18) | −0.0055 (14) | −0.0183 (14) | −0.0122 (14) |
C4 | 0.0601 (16) | 0.099 (2) | 0.0725 (17) | −0.0169 (15) | −0.0041 (14) | −0.0429 (16) |
C5 | 0.0717 (18) | 0.0737 (17) | 0.094 (2) | −0.0262 (15) | −0.0009 (16) | −0.0413 (15) |
C6 | 0.0693 (16) | 0.0480 (12) | 0.0651 (15) | −0.0148 (11) | −0.0040 (12) | −0.0193 (11) |
C7 | 0.0553 (13) | 0.0445 (11) | 0.0385 (11) | −0.0129 (9) | 0.0000 (9) | −0.0141 (9) |
C8 | 0.0640 (14) | 0.0505 (12) | 0.0462 (12) | −0.0160 (11) | −0.0087 (11) | −0.0104 (10) |
C9 | 0.0536 (13) | 0.0529 (11) | 0.0409 (12) | −0.0134 (10) | −0.0089 (10) | −0.0116 (9) |
C10 | 0.0568 (13) | 0.0477 (11) | 0.0338 (10) | −0.0093 (10) | −0.0079 (9) | −0.0112 (8) |
C11 | 0.0732 (16) | 0.0630 (14) | 0.0511 (14) | −0.0033 (12) | −0.0158 (12) | −0.0035 (11) |
C12 | 0.117 (3) | 0.0498 (14) | 0.0658 (17) | −0.0027 (15) | −0.0091 (17) | 0.0021 (12) |
C13 | 0.131 (3) | 0.0585 (16) | 0.0590 (16) | −0.0407 (18) | 0.0002 (17) | −0.0082 (12) |
C14 | 0.0855 (19) | 0.0792 (18) | 0.0674 (17) | −0.0391 (15) | −0.0066 (14) | −0.0155 (14) |
C15 | 0.0634 (15) | 0.0532 (12) | 0.0585 (14) | −0.0144 (11) | −0.0116 (12) | −0.0122 (10) |
C16 | 0.0682 (15) | 0.0689 (14) | 0.0531 (14) | −0.0278 (12) | −0.0043 (12) | −0.0164 (11) |
C17 | 0.0645 (15) | 0.0796 (16) | 0.0535 (14) | −0.0271 (13) | 0.0059 (12) | −0.0179 (13) |
C18 | 0.0740 (17) | 0.0854 (17) | 0.0586 (15) | −0.0279 (14) | 0.0098 (13) | −0.0216 (14) |
C19 | 0.118 (6) | 0.085 (5) | 0.071 (5) | −0.028 (4) | 0.022 (4) | −0.029 (4) |
C20 | 0.101 (4) | 0.097 (4) | 0.096 (5) | −0.024 (4) | 0.005 (4) | −0.041 (4) |
C21 | 0.089 (4) | 0.089 (4) | 0.066 (3) | −0.018 (3) | −0.024 (3) | −0.016 (3) |
C22 | 0.143 (7) | 0.104 (6) | 0.130 (6) | −0.056 (5) | −0.011 (6) | −0.037 (5) |
C19A | 0.095 (6) | 0.092 (6) | 0.058 (5) | −0.026 (5) | 0.018 (4) | −0.030 (5) |
C20A | 0.117 (6) | 0.110 (5) | 0.063 (4) | −0.030 (4) | −0.006 (4) | −0.031 (4) |
C21A | 0.139 (7) | 0.145 (7) | 0.099 (6) | −0.068 (6) | 0.015 (6) | −0.042 (5) |
C22A | 0.197 (11) | 0.108 (7) | 0.121 (8) | 0.018 (8) | −0.002 (9) | 0.009 (6) |
S1—O1 | 1.4179 (15) | C14—C15 | 1.384 (3) |
S1—O2 | 1.4329 (14) | C14—H14 | 0.9300 |
S1—N1 | 1.6488 (15) | C15—H15 | 0.9300 |
S1—C7 | 1.743 (2) | C16—C17 | 1.424 (3) |
O3—C8 | 1.205 (2) | C16—H16 | 0.9300 |
N1—C8 | 1.387 (3) | C17—C18 | 1.178 (3) |
N1—H1 | 0.8600 | C18—C19 | 1.472 (6) |
C1—C4 | 1.512 (4) | C18—C19A | 1.479 (7) |
C1—H1A | 0.9600 | C19—C20 | 1.550 (8) |
C1—H1B | 0.9600 | C19—H19A | 0.9700 |
C1—H1C | 0.9600 | C19—H19B | 0.9700 |
C2—C3 | 1.368 (3) | C20—C21 | 1.595 (6) |
C2—C7 | 1.380 (3) | C20—H20A | 0.9700 |
C2—H2 | 0.9300 | C20—H20B | 0.9700 |
C3—C4 | 1.377 (3) | C21—C22 | 1.374 (6) |
C3—H3 | 0.9300 | C21—H21A | 0.9700 |
C4—C5 | 1.365 (4) | C21—H21B | 0.9700 |
C5—C6 | 1.378 (3) | C22—H22A | 0.9600 |
C5—H5 | 0.9300 | C22—H22B | 0.9600 |
C6—C7 | 1.371 (3) | C22—H22C | 0.9600 |
C6—H6 | 0.9300 | C19A—C20A | 1.567 (9) |
C8—C9 | 1.493 (3) | C19A—H19C | 0.9700 |
C9—C16 | 1.335 (3) | C19A—H19D | 0.9700 |
C9—C10 | 1.482 (3) | C20A—C21A | 1.570 (8) |
C10—C15 | 1.373 (3) | C20A—H20C | 0.9700 |
C10—C11 | 1.382 (3) | C20A—H20D | 0.9700 |
C11—C12 | 1.373 (3) | C21A—C22A | 1.321 (8) |
C11—H11 | 0.9300 | C21A—H21C | 0.9700 |
C12—C13 | 1.358 (4) | C21A—H21D | 0.9700 |
C12—H12 | 0.9300 | C22A—H22D | 0.9600 |
C13—C14 | 1.365 (4) | C22A—H22E | 0.9600 |
C13—H13 | 0.9300 | C22A—H22F | 0.9600 |
O1—S1—O2 | 118.88 (10) | C15—C14—H14 | 120.0 |
O1—S1—N1 | 109.36 (9) | C10—C15—C14 | 120.8 (2) |
O2—S1—N1 | 103.78 (8) | C10—C15—H15 | 119.6 |
O1—S1—C7 | 109.46 (9) | C14—C15—H15 | 119.6 |
O2—S1—C7 | 109.04 (9) | C9—C16—C17 | 123.9 (2) |
N1—S1—C7 | 105.40 (9) | C9—C16—H16 | 118.1 |
C8—N1—S1 | 123.31 (13) | C17—C16—H16 | 118.1 |
C8—N1—H1 | 118.3 | C18—C17—C16 | 178.4 (3) |
S1—N1—H1 | 118.3 | C17—C18—C19 | 175.8 (7) |
C4—C1—H1A | 109.5 | C17—C18—C19A | 170.7 (8) |
C4—C1—H1B | 109.5 | C19—C18—C19A | 12.7 (12) |
H1A—C1—H1B | 109.5 | C18—C19—C20 | 108.9 (6) |
C4—C1—H1C | 109.5 | C18—C19—H19A | 109.9 |
H1A—C1—H1C | 109.5 | C20—C19—H19A | 109.9 |
H1B—C1—H1C | 109.5 | C18—C19—H19B | 109.9 |
C3—C2—C7 | 119.2 (2) | C20—C19—H19B | 109.9 |
C3—C2—H2 | 120.4 | H19A—C19—H19B | 108.3 |
C7—C2—H2 | 120.4 | C19—C20—C21 | 114.3 (9) |
C2—C3—C4 | 121.6 (3) | C19—C20—H20A | 108.7 |
C2—C3—H3 | 119.2 | C21—C20—H20A | 108.7 |
C4—C3—H3 | 119.2 | C19—C20—H20B | 108.7 |
C5—C4—C3 | 118.0 (2) | C21—C20—H20B | 108.7 |
C5—C4—C1 | 121.8 (3) | H20A—C20—H20B | 107.6 |
C3—C4—C1 | 120.2 (3) | C22—C21—C20 | 113.8 (6) |
C4—C5—C6 | 121.8 (2) | C22—C21—H21A | 108.8 |
C4—C5—H5 | 119.1 | C20—C21—H21A | 108.8 |
C6—C5—H5 | 119.1 | C22—C21—H21B | 108.8 |
C7—C6—C5 | 119.1 (2) | C20—C21—H21B | 108.8 |
C7—C6—H6 | 120.5 | H21A—C21—H21B | 107.7 |
C5—C6—H6 | 120.5 | C18—C19A—C20A | 110.9 (8) |
C6—C7—C2 | 120.2 (2) | C18—C19A—H19C | 109.5 |
C6—C7—S1 | 120.43 (17) | C20A—C19A—H19C | 109.5 |
C2—C7—S1 | 119.29 (16) | C18—C19A—H19D | 109.5 |
O3—C8—N1 | 121.30 (18) | C20A—C19A—H19D | 109.5 |
O3—C8—C9 | 124.1 (2) | H19C—C19A—H19D | 108.0 |
N1—C8—C9 | 114.59 (17) | C19A—C20A—C21A | 97.2 (11) |
C16—C9—C10 | 122.48 (18) | C19A—C20A—H20C | 112.3 |
C16—C9—C8 | 116.03 (19) | C21A—C20A—H20C | 112.3 |
C10—C9—C8 | 121.45 (17) | C19A—C20A—H20D | 112.3 |
C15—C10—C11 | 118.2 (2) | C21A—C20A—H20D | 112.3 |
C15—C10—C9 | 121.44 (19) | H20C—C20A—H20D | 109.9 |
C11—C10—C9 | 120.4 (2) | C22A—C21A—C20A | 135.1 (11) |
C12—C11—C10 | 120.7 (3) | C22A—C21A—H21C | 103.4 |
C12—C11—H11 | 119.6 | C20A—C21A—H21C | 103.4 |
C10—C11—H11 | 119.6 | C22A—C21A—H21D | 103.4 |
C13—C12—C11 | 120.5 (3) | C20A—C21A—H21D | 103.4 |
C13—C12—H12 | 119.8 | H21C—C21A—H21D | 105.2 |
C11—C12—H12 | 119.8 | C21A—C22A—H22D | 109.5 |
C12—C13—C14 | 119.8 (2) | C21A—C22A—H22E | 109.5 |
C12—C13—H13 | 120.1 | H22D—C22A—H22E | 109.5 |
C14—C13—H13 | 120.1 | C21A—C22A—H22F | 109.5 |
C13—C14—C15 | 120.0 (3) | H22D—C22A—H22F | 109.5 |
C13—C14—H14 | 120.0 | H22E—C22A—H22F | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.32 | 2.947 (2) | 130 |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H23NO3S |
Mr | 381.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.8186 (10), 9.8201 (9), 11.3352 (13) |
α, β, γ (°) | 81.470 (8), 76.308 (9), 75.042 (9) |
V (Å3) | 1021.46 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.18 |
Crystal size (mm) | 0.42 × 0.38 × 0.32 |
Data collection | |
Diffractometer | Agilent Xcalibur (Atlas, Gemini ultra) |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011) |
Tmin, Tmax | 0.928, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9118, 4425, 3005 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.641 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.096, 1.00 |
No. of reflections | 4425 |
No. of parameters | 285 |
No. of restraints | 170 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.28 |
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.32 | 2.947 (2) | 130 |
Symmetry code: (i) −x+1, −y+1, −z. |
Acknowledgements
The work was supported financially by the Chaohu College Project (XLY–201105).
References
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Cheng, D., Ling, F., Li, Z.-X., Yao, W.-J. & Ma, C. (2012). Org. Lett. 14, 3146–3149. Web of Science CSD CrossRef CAS PubMed Google Scholar
Ochiai, B., Tomita, I. & Endo, T. (1999). Macromolecules, 32, 238–240. Web of Science CrossRef CAS Google Scholar
Saito, S., Kawasaki, T., Tsuboya, N. & Yamamoto, Y. (2001). J. Org. Chem. 66, 796–802. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Conjugated enynes can be used in the synthesis of polymers (Ochiai et al., 1999) and in the selective construction of aromatic frameworks (Saito et al., 2001). Here, we report the crystal structure of the title enyne compound.
The molecular structure of the title compound is shown in Figure 1, the ORTEP diagram shows that the structure adopts the E isomer, the double bond and triple bond are within normal ranges. The benzene C2–C7 and C10–C15 rings are tilted relative to each other by 23.79 (5)°. The chain C19—C22 is disorder. A view of the crystal packing for the title compound is illustrated in Fig. 2, the crystal structure is stabilized by N—H···O hydrogen bonds.