(E)-2-Phenyl-N-tosyl-non-2-en-4-ynamide.

The mol-ecule 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 mol-ecules, 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

C22H23NO3S

M = 381.47

Triclinic,

a = 9.8186 (10) Å

b = 9.8201 (9) Å

c = 11.3352 (13) Å

α = 81.470 (8)°

β = 76.308 (9)°

γ = 75.042 (9)°

V = 1021.46 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.42 × 0.38 × 0.32 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.928, T max = 0.945

9118 measured reflections

4425 independent reflections

3005 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.096

S = 1.00

4425 reflections

285 parameters

170 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812048489/xu5655sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048489/xu5655Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048489/xu5655Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) .