(E)-2-Phenyl-N-tosyl­non-2-en-4-ynamide

Meng, X.-Z.; Wan, X.-J.

doi:10.1107/S1600536812048489

organic compounds

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ISSN: 2056-9890

Volume 69| Part 1| January 2013| Page o78

https://doi.org/10.1107/S1600536812048489

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(E)-2-Phenyl-N-tosylnon-2-en-4-ynamide

Xiang-Zhen Meng ^a and Xin-Jun Wan ^a ^*

^aDepartment of Chemistry and Life Science, Chaohu College, Anhui Province, People's Republic of China
^*Correspondence e-mail: wzys2012@126.com

(Received 22 November 2012; accepted 26 November 2012; online 12 December 2012)

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

C₂₂H₂₃NO₃S
M_r = 381.47
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.096
S = 1.00
4425 reflections
285 parameters
170 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) -x+1, -y+1, -z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812048489/xu5655sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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 top

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 column chromatography 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.

Structure description top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The crystal packing diagram.

(E)-2-Phenyl-N-tosylnon-2-en-4-ynamide top

Crystal data top

C₂₂H₂₃NO₃S	Z = 2
M_r = 381.47	F(000) = 404
Triclinic, P1	D_x = 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

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	4425 independent reflections
Radiation source: fine-focus sealed tube	3005 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 10.3592 pixels mm^-1	θ_max = 27.1°, θ_min = 2.9°
ω scans	h = −12→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
T_min = 0.928, T_max = 0.945	l = −14→13
9118 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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0145P)² + 0.450P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4425 reflections	Δρ_max = 0.19 e Å⁻³
285 parameters	Δρ_min = −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)

Crystal data top

C₂₂H₂₃NO₃S	γ = 75.042 (9)°
M_r = 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)°

Data collection top

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	4425 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3005 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.945	R_int = 0.028
9118 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	170 restraints
wR(F²) = 0.096	H-atom parameters constrained
S = 1.00	Δρ_max = 0.19 e Å⁻³
4425 reflections	Δρ_min = −0.28 e Å⁻³
285 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.928, 0.945
No. of measured, independent and observed [I > 2σ(I)] reflections	9118, 4425, 3005
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.28

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

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