4-(3-Nitro­phen­yl)-3-(phenyl­sulfon­yl)but-3-en-2-one

Wang, Y.; Pei, W.

doi:10.1107/S1600536808005370

organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Page o640

doi:10.1107/S1600536808005370

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4-(3-Nitrophenyl)-3-(phenylsulfonyl)but-3-en-2-one

Yongjiang Wang ^a and Wen Pei ^b ^*

^aCollege of Biological and Chemical Engineering, Zhejiang University of Science and Technology, Hangzhou 310023, People's Republic of China, and ^bCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: river0301@163.com

(Received 29 November 2007; accepted 26 February 2008; online 29 February 2008)

The C=C double bond in the title molecule, C₁₆H₁₃NO₅S, has an E configuration. The crystal structure is stabilized by C—H⋯O hydrogen bonds. There is also a weak C—H⋯π-ring interaction in the structure.

Related literature

For related literature, see: Pei (1998 ). For the chemical preparation, see: Wada et al. (1996 ).

Experimental

Crystal data

C₁₆H₁₃NO₅S
M_r = 331.34
Monoclinic, P 2₁ /n
a = 7.957 (2) Å
b = 10.580 (3) Å
c = 18.271 (6) Å
β = 95.976 (14)°
V = 1529.7 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (1) K
0.25 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.923, T_max = 0.954
14836 measured reflections
3507 independent reflections
2890 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.05
3507 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4ⁱ	0.93	2.60	3.104 (2)	114
C8—H8⋯O5ⁱⁱ	0.93	2.53	3.321 (2)	143
C10—H10⋯O3ⁱⁱⁱ	0.93	2.54	3.364 (2)	148
C13—H13⋯O5ⁱⁱⁱ	0.93	2.59	3.433 (2)	152
C12—H12⋯O4	0.93	2.52	2.903 (2)	105
C16—H16⋯O4ⁱ	0.93	2.60	3.524 (2)	176
C9—H9⋯Cg1ⁱⁱ	0.93	2.80	3.608 (2)	145
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z. Cg1 is the centroid of the C11–C16 phenyl ring.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005370/fb2081sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005370/fb2081Isup2.hkl

checkCIF report

Comment top

Phenylsulfonyl-3-alken-2-ones have been used as asymmetric synthetic reagents (Wada et al., 1996) as well as electron-deficient dienophiles. They have been applied in asymmetric Diels–Alder chemistry (Pei, 1998). The title compound has been prepared and studied in order to get a better understanding about the synthesis of phenylsulfonyl-3-alken-2-ones. The molecular structure, Fig. 1, shows that an E-configuration is present on the C=C double bond between the atoms C1 and C4. There is also present a C—H···π-electron ring interaction in the structure. It involves the phenyl ring C11–C16 with centroid Cg1 (Table 1).

Related literature top

For related literature, see: Pei (1998). For chemical preparation, see:Wada et al. (1996).

Experimental top

The title compound was prepared according to the procedure of Wada et al. (1996). Diffraction quality crystals were obtained by recrystallization from ethanol solution by slow evaporation at room temperature. The average dimension of the block crystals was about 0.2 mm.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top

Fig. 1. View of the title molecule showing the atom labelling scheme. The displacement ellipsoids are drawn at the 40% probability level.

4-(3-Nitrophenyl)-3-(phenylsulfonyl)but-3-en-2-one top

Crystal data top

C₁₆H₁₃NO₅S	F(000) = 688.00
M_r = 331.34	D_x = 1.439 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 12472 reflections
a = 7.957 (2) Å	θ = 3.2–27.5°
b = 10.580 (3) Å	µ = 0.24 mm⁻¹
c = 18.271 (6) Å	T = 298 K
β = 95.976 (14)°	Block, colourless
V = 1529.7 (8) Å³	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	3507 independent reflections
Graphite monochromator	2890 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→10
T_min = 0.923, T_max = 0.954	k = −13→13
14836 measured reflections	l = −23→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.106	w = 1/[σ²(F_o²) + (0.0516P)² + 0.4387P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3507 reflections	Δρ_max = 0.34 e Å⁻³
210 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
42 constraints	Extinction coefficient: 0.0097 (17)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₆H₁₃NO₅S	V = 1529.7 (8) Å³
M_r = 331.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.957 (2) Å	µ = 0.24 mm⁻¹
b = 10.580 (3) Å	T = 298 K
c = 18.271 (6) Å	0.25 × 0.20 × 0.20 mm
β = 95.976 (14)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	3507 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2890 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.954	R_int = 0.027
14836 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.05	Δρ_max = 0.34 e Å⁻³
3507 reflections	Δρ_min = −0.40 e Å⁻³
210 parameters

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
S1	0.84122 (5)	0.43647 (4)	0.25330 (2)	0.03894 (14)
O1	0.99494 (16)	0.40871 (14)	0.10399 (8)	0.0607 (4)
O2	0.02708 (17)	0.12269 (16)	0.11304 (9)	0.0674 (4)
O3	−0.02286 (17)	0.14516 (19)	−0.00423 (9)	0.0806 (5)
O4	0.89564 (17)	0.56378 (11)	0.24210 (8)	0.0568 (4)
O5	0.72060 (15)	0.41361 (14)	0.30472 (7)	0.0566 (4)
N1	0.07214 (18)	0.14380 (15)	0.05295 (9)	0.0508 (4)
C1	0.75310 (18)	0.37984 (14)	0.16622 (8)	0.0349 (3)
C2	0.8455 (2)	0.42725 (15)	0.10363 (9)	0.0418 (4)
C3	0.7499 (3)	0.5076 (2)	0.04658 (14)	0.0770 (7)
H31	0.8105	0.5121	0.0039	0.116*
H32	0.7371	0.5910	0.0659	0.116*
H33	0.6404	0.4713	0.0332	0.116*
C4	0.61399 (18)	0.30895 (15)	0.16516 (8)	0.0370 (3)
H4	0.5739	0.2956	0.2106	0.044*
C5	0.51608 (18)	0.24949 (14)	0.10202 (8)	0.0357 (3)
C6	0.34611 (19)	0.22278 (15)	0.10721 (9)	0.0376 (3)
H6	0.2974	0.2406	0.1502	0.045*
C7	0.25178 (19)	0.16961 (15)	0.04761 (9)	0.0385 (3)
C8	0.3182 (2)	0.13919 (17)	−0.01672 (9)	0.0473 (4)
H8	0.2507	0.1052	−0.0565	0.057*
C9	0.4884 (2)	0.16088 (19)	−0.02025 (10)	0.0526 (4)
H9	0.5374	0.1386	−0.0625	0.063*
C10	0.5862 (2)	0.21504 (17)	0.03795 (10)	0.0462 (4)
H10	0.7005	0.2289	0.0346	0.055*
C11	1.02028 (18)	0.34291 (15)	0.28003 (8)	0.0369 (3)
C12	1.1754 (2)	0.40079 (18)	0.29545 (9)	0.0453 (4)
H12	1.1883	0.4867	0.2868	0.054*
C13	1.3113 (2)	0.3282 (2)	0.32406 (11)	0.0590 (5)
H13	1.4168	0.3654	0.3350	0.071*
C14	1.2909 (3)	0.2017 (2)	0.33632 (12)	0.0655 (6)
H14	1.3824	0.1538	0.3563	0.079*
C15	1.1369 (3)	0.1452 (2)	0.31942 (13)	0.0658 (6)
H15	1.1252	0.0589	0.3271	0.079*
C16	0.9995 (2)	0.21509 (17)	0.29120 (11)	0.0524 (4)
H16	0.8947	0.1770	0.2799	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0325 (2)	0.0432 (2)	0.0403 (2)	0.00241 (15)	−0.00025 (15)	−0.00634 (16)
O1	0.0424 (7)	0.0742 (9)	0.0676 (9)	−0.0004 (6)	0.0163 (6)	0.0104 (7)
O2	0.0468 (7)	0.0850 (11)	0.0725 (10)	−0.0159 (7)	0.0157 (7)	−0.0016 (8)
O3	0.0393 (7)	0.1266 (15)	0.0713 (10)	0.0022 (8)	−0.0154 (7)	−0.0245 (10)
O4	0.0583 (8)	0.0375 (6)	0.0717 (9)	0.0017 (5)	−0.0075 (7)	−0.0083 (6)
O5	0.0395 (6)	0.0887 (10)	0.0420 (7)	0.0056 (6)	0.0062 (5)	−0.0108 (6)
N1	0.0348 (7)	0.0560 (9)	0.0606 (10)	−0.0022 (6)	0.0003 (7)	−0.0121 (7)
C1	0.0321 (7)	0.0371 (7)	0.0346 (7)	0.0026 (6)	−0.0009 (6)	0.0016 (6)
C2	0.0411 (8)	0.0418 (8)	0.0423 (9)	−0.0043 (7)	0.0038 (7)	0.0017 (6)
C3	0.0709 (14)	0.0856 (16)	0.0746 (15)	0.0032 (12)	0.0080 (12)	0.0424 (13)
C4	0.0335 (7)	0.0425 (8)	0.0344 (7)	0.0013 (6)	0.0012 (6)	0.0035 (6)
C5	0.0325 (7)	0.0384 (7)	0.0355 (7)	0.0008 (6)	0.0004 (6)	0.0036 (6)
C6	0.0345 (7)	0.0437 (8)	0.0348 (8)	−0.0007 (6)	0.0047 (6)	0.0001 (6)
C7	0.0319 (7)	0.0412 (8)	0.0413 (8)	0.0020 (6)	−0.0006 (6)	0.0001 (6)
C8	0.0476 (9)	0.0549 (10)	0.0377 (8)	0.0027 (8)	−0.0039 (7)	−0.0071 (7)
C9	0.0516 (10)	0.0671 (12)	0.0406 (9)	0.0026 (9)	0.0128 (8)	−0.0096 (8)
C10	0.0356 (8)	0.0568 (10)	0.0472 (9)	0.0010 (7)	0.0086 (7)	−0.0031 (8)
C11	0.0317 (7)	0.0447 (8)	0.0336 (7)	0.0004 (6)	0.0004 (6)	−0.0030 (6)
C12	0.0347 (8)	0.0575 (10)	0.0435 (9)	−0.0072 (7)	0.0031 (7)	−0.0021 (7)
C13	0.0308 (8)	0.0930 (16)	0.0526 (11)	0.0023 (9)	0.0016 (7)	−0.0053 (10)
C14	0.0525 (11)	0.0838 (15)	0.0587 (12)	0.0304 (11)	−0.0011 (9)	−0.0044 (11)
C15	0.0724 (14)	0.0492 (11)	0.0744 (14)	0.0161 (10)	0.0006 (11)	−0.0012 (9)
C16	0.0471 (10)	0.0451 (9)	0.0633 (11)	−0.0017 (7)	−0.0020 (8)	−0.0047 (8)

Geometric parameters (Å, º) top

S1—O5	1.4317 (13)	C6—H6	0.9300
S1—O4	1.4360 (13)	C7—C8	1.376 (2)
S1—C11	1.7617 (16)	C8—C9	1.382 (3)
S1—C1	1.7747 (16)	C8—H8	0.9300
O1—C2	1.204 (2)	C9—C10	1.375 (2)
O2—N1	1.211 (2)	C9—H9	0.9300
O3—N1	1.224 (2)	C10—H10	0.9300
N1—C7	1.468 (2)	C11—C16	1.380 (2)
C1—C4	1.335 (2)	C11—C12	1.381 (2)
C1—C2	1.508 (2)	C12—C13	1.384 (3)
C2—C3	1.491 (3)	C12—H12	0.9300
C3—H31	0.9600	C13—C14	1.369 (3)
C3—H32	0.9600	C13—H13	0.9300
C3—H33	0.9600	C14—C15	1.369 (3)
C4—C5	1.465 (2)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.375 (3)
C5—C6	1.394 (2)	C15—H15	0.9300
C5—C10	1.396 (2)	C16—H16	0.9300
C6—C7	1.377 (2)

O5—S1—O4	118.99 (9)	C8—C7—C6	123.02 (15)
O5—S1—C11	107.53 (8)	C8—C7—N1	118.44 (14)
O4—S1—C11	108.63 (8)	C6—C7—N1	118.54 (14)
O5—S1—C1	107.57 (8)	C7—C8—C9	117.81 (15)
O4—S1—C1	106.61 (8)	C7—C8—H8	121.1
C11—S1—C1	106.95 (7)	C9—C8—H8	121.1
O2—N1—O3	124.14 (16)	C10—C9—C8	120.74 (16)
O2—N1—C7	118.48 (15)	C10—C9—H9	119.6
O3—N1—C7	117.38 (16)	C8—C9—H9	119.6
C4—C1—C2	130.13 (14)	C9—C10—C5	120.92 (15)
C4—C1—S1	116.88 (12)	C9—C10—H10	119.5
C2—C1—S1	112.89 (11)	C5—C10—H10	119.5
O1—C2—C3	121.90 (17)	C16—C11—C12	121.53 (15)
O1—C2—C1	120.05 (15)	C16—C11—S1	119.05 (12)
C3—C2—C1	117.76 (16)	C12—C11—S1	119.18 (13)
C2—C3—H31	109.5	C11—C12—C13	118.54 (18)
C2—C3—H32	109.5	C11—C12—H12	120.7
H31—C3—H32	109.5	C13—C12—H12	120.7
C2—C3—H33	109.5	C14—C13—C12	120.20 (18)
H31—C3—H33	109.5	C14—C13—H13	119.9
H32—C3—H33	109.5	C12—C13—H13	119.9
C1—C4—C5	128.65 (14)	C15—C14—C13	120.55 (18)
C1—C4—H4	115.7	C15—C14—H14	119.7
C5—C4—H4	115.7	C13—C14—H14	119.7
C6—C5—C10	118.61 (14)	C14—C15—C16	120.5 (2)
C6—C5—C4	118.26 (14)	C14—C15—H15	119.7
C10—C5—C4	123.10 (14)	C16—C15—H15	119.7
C7—C6—C5	118.80 (14)	C15—C16—C11	118.64 (18)
C7—C6—H6	120.6	C15—C16—H16	120.7
C5—C6—H6	120.6	C11—C16—H16	120.7

O4—S1—C1—C2	36.47 (12)	C4—C1—C2—C3	58.5 (2)
O4—S1—C1—C4	−140.16 (11)	C1—C4—C5—C6	−155.46 (15)
O4—S1—C11—C12	8.06 (15)	C1—C4—C5—C10	26.5 (2)
O4—S1—C11—C16	−177.55 (14)	C4—C5—C6—C7	178.54 (13)
O5—S1—C1—C2	165.12 (10)	C4—C5—C10—C9	−179.12 (15)
O5—S1—C1—C4	−11.50 (13)	C6—C5—C10—C9	2.9 (2)
O5—S1—C11—C12	−121.99 (13)	C10—C5—C6—C7	−3.4 (2)
O5—S1—C11—C16	52.59 (15)	C5—C6—C7—N1	−178.84 (13)
C1—S1—C11—C12	122.77 (13)	C5—C6—C7—C8	1.3 (2)
C1—S1—C11—C16	−62.81 (15)	N1—C7—C8—C9	−178.34 (14)
C11—S1—C1—C2	−79.59 (11)	C6—C7—C8—C9	1.6 (2)
C11—S1—C1—C4	103.79 (12)	C7—C8—C9—C10	−2.2 (2)
O2—N1—C7—C6	−28.2 (2)	C8—C9—C10—C5	−0.0 (2)
O2—N1—C7—C8	151.86 (15)	S1—C11—C12—C13	173.00 (13)
O3—N1—C7—C6	151.83 (16)	S1—C11—C16—C15	−173.37 (15)
O3—N1—C7—C8	−28.2 (2)	C12—C11—C16—C15	1.0 (2)
S1—C1—C2—O1	56.37 (18)	C16—C11—C12—C13	−1.3 (2)
S1—C1—C2—C3	−117.54 (15)	C11—C12—C13—C14	0.2 (2)
S1—C1—C4—C5	−179.53 (12)	C12—C13—C14—C15	1.0 (3)
C2—C1—C4—C5	4.5 (2)	C13—C14—C15—C16	−1.3 (3)
C4—C1—C2—O1	−127.56 (18)	C14—C15—C16—C11	0.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.60	3.104 (2)	114
C8—H8···O5ⁱⁱ	0.93	2.53	3.321 (2)	143
C10—H10···O3ⁱⁱⁱ	0.93	2.54	3.364 (2)	148
C13—H13···O5ⁱⁱⁱ	0.93	2.59	3.433 (2)	152
C12—H12···O4	0.93	2.52	2.903 (2)	105
C16—H16···O4ⁱ	0.93	2.60	3.524 (2)	176
C9—H9···Cg1ⁱⁱ	0.93	2.80	3.608 (2)	145

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃NO₅S
M_r	331.34
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.957 (2), 10.580 (3), 18.271 (6)
β (°)	95.976 (14)
V (Å³)	1529.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.923, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	14836, 3507, 2890
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.05
No. of reflections	3507
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.40

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.603	3.104 (2)	114
C8—H8···O5ⁱⁱ	0.93	2.530	3.321 (2)	143
C10—H10···O3ⁱⁱⁱ	0.93	2.541	3.364 (2)	148
C13—H13···O5ⁱⁱⁱ	0.93	2.586	3.433 (2)	152
C12—H12···O4	0.93	2.52	2.903 (2)	105
C16—H16···O4ⁱ	0.93	2.60	3.524 (2)	176
C9—H9···Cg1ⁱⁱ	0.93	2.80	3.608 (2)	145

Symmetry codes: (i) −x+3/2, y−1/2, −z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1, y, z.

Acknowledgements

This work was supported by the Open Foundation of the Key Discipline of Industrial Catalysis.

References

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