Literature DB >> 22606161

4,4-Dimethyl-2-[3-nitro-2-phenyl-1-(phenyl-sulfan-yl)prop-yl]-4,5-dihydro-1,3-oxazole.

Ignez Caracelli, Julio Zukerman-Schpector, José A F P Villar, Alfredo R M Oliveira, Edward R T Tiekink.   

Abstract

In the title compound, C(20)H(22)N(2)O(3)S, the oxazoline ring is planar (r.m.s. deviation = 0.045 Å) and forms dihedral angles of 47.24 (8) and 10.11 (8)° with the S- and C-bound phenyl rings, respectively. The nitro group lies to the same side of the mol-ecule as the oxazoline ring but is orientated so as not to inter-act with the ring. Linear supra-molecular chains along [010] are formed via C-H⋯O and C-H⋯S contacts. Chains are consolidated into a three-dimensional architecture by C-H⋯π and van der Waals inter-actions.

Entities:  

Year:  2012        PMID： 22606161      PMCID： PMC3344158          DOI： 10.1107/S1600536812012512

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background on the biological activities of Rolipram, see: de Visser et al. (2008 ▶). For the synthesis of the title compound, see Villar (2008 ▶); Oliveira et al. (2007 ▶).

Experimental

Crystal data

C20H22N2O3S M = 370.47 Monoclinic, a = 15.339 (3) Å b = 5.7040 (8) Å c = 22.786 (4) Å β = 107.166 (2)° V = 1904.8 (6) Å3 Z = 4 Mo Kα radiation μ = 0.19 mm−1 T = 98 K 0.25 × 0.15 × 0.15 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.809, T max = 1.000 15389 measured reflections 4362 independent reflections 4146 reflections with I > 2σ(I) R int = 0.035 Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.114 S = 1.11 4362 reflections 235 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.33 e Å−3 Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), DIAMOND (Brandenburg, 2006 ▶) and MarvinSketch (ChemAxon, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012512/qk2035sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012512/qk2035Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812012512/qk2035Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H22N2O3SF(000) = 784
Mr = 370.47Dx = 1.292 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10219 reflections
a = 15.339 (3) Åθ = 1.9–40.6°
b = 5.7040 (8) ŵ = 0.19 mm−1
c = 22.786 (4) ÅT = 98 K
β = 107.166 (2)°Block, colourless
V = 1904.8 (6) Å30.25 × 0.15 × 0.15 mm
Z = 4
Rigaku AFC12K/SATURN724 diffractometer4362 independent reflections
Radiation source: fine-focus sealed tube4146 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −19→19
Tmin = 0.809, Tmax = 1.000k = −7→7
15389 measured reflectionsl = −29→29
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0504P)2 + 0.9546P] where P = (Fo2 + 2Fc2)/3
4362 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
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 > 2σ(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.
xyzUiso*/Ueq
S10.19877 (2)0.17504 (7)0.813988 (16)0.02204 (11)
O10.27948 (8)0.1328 (2)0.95576 (5)0.0253 (2)
O20.50324 (9)0.8943 (3)0.91166 (7)0.0465 (4)
O30.53747 (8)0.5316 (2)0.93550 (6)0.0361 (3)
N10.19037 (9)0.4465 (2)0.95984 (6)0.0224 (3)
N20.48312 (9)0.6943 (3)0.92173 (6)0.0265 (3)
C10.24888 (9)0.4033 (3)0.87082 (6)0.0180 (3)
H10.21590.55400.85710.022*
C20.23715 (9)0.3355 (3)0.93164 (6)0.0176 (3)
C30.25828 (11)0.1010 (3)1.01329 (7)0.0271 (3)
H3A0.31420.11201.04860.033*
H3B0.2293−0.05341.01440.033*
C40.19137 (10)0.3029 (3)1.01474 (7)0.0230 (3)
C50.09488 (12)0.2111 (4)1.00615 (8)0.0344 (4)
H5A0.07540.11730.96850.052*
H5B0.05310.34361.00300.052*
H5C0.09430.11351.04140.052*
C60.22443 (14)0.4495 (3)1.07286 (8)0.0347 (4)
H6A0.28630.50631.07720.052*
H6B0.22480.35321.10860.052*
H6C0.18350.58351.07030.052*
C70.09006 (10)0.1354 (3)0.82616 (6)0.0190 (3)
C80.02137 (10)0.3010 (3)0.80472 (7)0.0205 (3)
H80.03370.44240.78660.025*
C9−0.06542 (10)0.2590 (3)0.80984 (7)0.0240 (3)
H9−0.11190.37370.79610.029*
C10−0.08439 (10)0.0499 (3)0.83492 (7)0.0248 (3)
H10−0.14430.01950.83710.030*
C11−0.01562 (11)−0.1148 (3)0.85681 (7)0.0250 (3)
H11−0.0285−0.25750.87410.030*
C120.07213 (11)−0.0708 (3)0.85336 (7)0.0224 (3)
H120.1196−0.18100.86950.027*
C130.35030 (9)0.4353 (3)0.87367 (6)0.0184 (3)
H130.38500.29170.89230.022*
C140.38517 (10)0.6438 (3)0.91664 (7)0.0220 (3)
H14A0.34760.78380.90060.026*
H14B0.37940.60820.95790.026*
C150.36148 (9)0.4727 (3)0.81003 (6)0.0179 (3)
C160.40566 (10)0.3047 (3)0.78483 (7)0.0224 (3)
H160.43030.16880.80790.027*
C170.41408 (11)0.3347 (3)0.72591 (7)0.0255 (3)
H170.44430.21900.70900.031*
C180.37849 (10)0.5328 (3)0.69199 (7)0.0251 (3)
H180.38390.55280.65180.030*
C190.33489 (11)0.7019 (3)0.71705 (7)0.0245 (3)
H190.31080.83840.69410.029*
C200.32642 (10)0.6719 (3)0.77579 (7)0.0220 (3)
H200.29650.78830.79270.026*
U11U22U33U12U13U23
S10.01822 (19)0.0306 (2)0.01930 (19)0.00031 (14)0.00869 (14)−0.00508 (14)
O10.0314 (6)0.0267 (6)0.0215 (5)0.0077 (5)0.0136 (5)0.0083 (4)
O20.0322 (7)0.0477 (8)0.0588 (9)−0.0099 (6)0.0124 (6)0.0209 (7)
O30.0209 (6)0.0469 (8)0.0387 (7)0.0037 (5)0.0060 (5)0.0024 (6)
N10.0230 (6)0.0289 (7)0.0175 (6)0.0028 (5)0.0094 (5)0.0014 (5)
N20.0193 (6)0.0395 (8)0.0200 (6)−0.0034 (5)0.0048 (5)0.0044 (6)
C10.0162 (6)0.0228 (7)0.0163 (6)0.0023 (5)0.0066 (5)0.0009 (5)
C20.0151 (6)0.0206 (7)0.0169 (6)0.0001 (5)0.0047 (5)0.0014 (5)
C30.0301 (8)0.0326 (9)0.0223 (7)0.0010 (7)0.0135 (6)0.0094 (7)
C40.0239 (7)0.0304 (8)0.0167 (7)−0.0033 (6)0.0089 (6)0.0007 (6)
C50.0269 (8)0.0541 (11)0.0263 (8)−0.0091 (8)0.0143 (7)−0.0035 (8)
C60.0479 (11)0.0374 (10)0.0208 (8)−0.0101 (8)0.0133 (7)−0.0045 (7)
C70.0185 (6)0.0234 (7)0.0167 (6)0.0006 (5)0.0077 (5)−0.0029 (5)
C80.0215 (7)0.0229 (7)0.0173 (6)−0.0005 (5)0.0058 (5)−0.0001 (5)
C90.0198 (7)0.0304 (8)0.0216 (7)0.0043 (6)0.0059 (6)0.0008 (6)
C100.0216 (7)0.0329 (8)0.0228 (7)−0.0028 (6)0.0110 (6)−0.0037 (6)
C110.0319 (8)0.0240 (8)0.0232 (7)−0.0022 (6)0.0142 (6)−0.0007 (6)
C120.0261 (7)0.0230 (7)0.0200 (7)0.0048 (6)0.0099 (6)−0.0001 (6)
C130.0156 (6)0.0238 (7)0.0175 (6)0.0032 (5)0.0074 (5)0.0034 (5)
C140.0177 (7)0.0307 (8)0.0190 (7)−0.0012 (6)0.0076 (5)0.0011 (6)
C150.0149 (6)0.0226 (7)0.0180 (6)−0.0001 (5)0.0073 (5)0.0022 (5)
C160.0211 (7)0.0238 (7)0.0250 (7)0.0026 (6)0.0108 (6)0.0015 (6)
C170.0245 (7)0.0311 (8)0.0247 (8)−0.0004 (6)0.0133 (6)−0.0044 (6)
C180.0221 (7)0.0373 (9)0.0168 (6)−0.0059 (6)0.0071 (6)−0.0012 (6)
C190.0238 (7)0.0295 (8)0.0193 (7)0.0002 (6)0.0051 (6)0.0059 (6)
C200.0229 (7)0.0247 (8)0.0199 (7)0.0038 (6)0.0086 (6)0.0023 (6)
S1—C71.7837 (15)C8—C91.391 (2)
S1—C11.8372 (15)C8—H80.9500
O1—C21.3601 (18)C9—C101.390 (2)
O1—C31.4520 (17)C9—H90.9500
O2—N21.221 (2)C10—C111.390 (2)
O3—N21.2250 (19)C10—H100.9500
N1—C21.2652 (19)C11—C121.394 (2)
N1—C41.4914 (19)C11—H110.9500
N2—C141.5004 (19)C12—H120.9500
C1—C21.4996 (19)C13—C151.5246 (18)
C1—C131.5487 (19)C13—C141.533 (2)
C1—H11.0000C13—H131.0000
C3—C41.549 (2)C14—H14A0.9900
C3—H3A0.9900C14—H14B0.9900
C3—H3B0.9900C15—C161.392 (2)
C4—C61.521 (2)C15—C201.393 (2)
C4—C51.527 (2)C16—C171.397 (2)
C5—H5A0.9800C16—H160.9500
C5—H5B0.9800C17—C181.387 (2)
C5—H5C0.9800C17—H170.9500
C6—H6A0.9800C18—C191.389 (2)
C6—H6B0.9800C18—H180.9500
C6—H6C0.9800C19—C201.393 (2)
C7—C81.392 (2)C19—H190.9500
C7—C121.394 (2)C20—H200.9500
C7—S1—C1101.31 (6)C7—C8—H8120.1
C2—O1—C3105.29 (11)C10—C9—C8120.25 (14)
C2—N1—C4106.52 (13)C10—C9—H9119.9
O2—N2—O3124.43 (14)C8—C9—H9119.9
O2—N2—C14117.89 (14)C9—C10—C11119.91 (14)
O3—N2—C14117.67 (14)C9—C10—H10120.0
C2—C1—C13112.63 (11)C11—C10—H10120.0
C2—C1—S1109.23 (10)C10—C11—C12120.06 (15)
C13—C1—S1108.62 (9)C10—C11—H11120.0
C2—C1—H1108.8C12—C11—H11120.0
C13—C1—H1108.8C7—C12—C11119.83 (14)
S1—C1—H1108.8C7—C12—H12120.1
N1—C2—O1119.64 (13)C11—C12—H12120.1
N1—C2—C1125.53 (14)C15—C13—C14112.52 (12)
O1—C2—C1114.79 (12)C15—C13—C1111.73 (11)
O1—C3—C4104.63 (12)C14—C13—C1105.96 (11)
O1—C3—H3A110.8C15—C13—H13108.8
C4—C3—H3A110.8C14—C13—H13108.8
O1—C3—H3B110.8C1—C13—H13108.8
C4—C3—H3B110.8N2—C14—C13110.55 (12)
H3A—C3—H3B108.9N2—C14—H14A109.5
N1—C4—C6110.28 (13)C13—C14—H14A109.5
N1—C4—C5108.13 (13)N2—C14—H14B109.5
C6—C4—C5111.19 (13)C13—C14—H14B109.5
N1—C4—C3103.49 (11)H14A—C14—H14B108.1
C6—C4—C3111.99 (14)C16—C15—C20119.01 (13)
C5—C4—C3111.44 (14)C16—C15—C13120.08 (13)
C4—C5—H5A109.5C20—C15—C13120.90 (13)
C4—C5—H5B109.5C15—C16—C17120.45 (14)
H5A—C5—H5B109.5C15—C16—H16119.8
C4—C5—H5C109.5C17—C16—H16119.8
H5A—C5—H5C109.5C18—C17—C16120.16 (15)
H5B—C5—H5C109.5C18—C17—H17119.9
C4—C6—H6A109.5C16—C17—H17119.9
C4—C6—H6B109.5C17—C18—C19119.66 (14)
H6A—C6—H6B109.5C17—C18—H18120.2
C4—C6—H6C109.5C19—C18—H18120.2
H6A—C6—H6C109.5C18—C19—C20120.17 (15)
H6B—C6—H6C109.5C18—C19—H19119.9
C8—C7—C12120.02 (13)C20—C19—H19119.9
C8—C7—S1120.32 (11)C19—C20—C15120.54 (14)
C12—C7—S1119.50 (11)C19—C20—H20119.7
C9—C8—C7119.85 (14)C15—C20—H20119.7
C9—C8—H8120.1
C7—S1—C1—C248.49 (11)C8—C7—C12—C112.6 (2)
C7—S1—C1—C13171.69 (10)S1—C7—C12—C11−172.84 (12)
C4—N1—C2—O1−3.18 (18)C10—C11—C12—C7−2.0 (2)
C4—N1—C2—C1174.70 (13)C2—C1—C13—C15172.60 (12)
C3—O1—C2—N1−1.22 (18)S1—C1—C13—C1551.47 (14)
C3—O1—C2—C1−179.33 (12)C2—C1—C13—C14−64.52 (15)
C13—C1—C2—N1123.03 (16)S1—C1—C13—C14174.35 (9)
S1—C1—C2—N1−116.19 (15)O2—N2—C14—C13127.19 (16)
C13—C1—C2—O1−58.99 (16)O3—N2—C14—C13−52.53 (18)
S1—C1—C2—O161.79 (14)C15—C13—C14—N2−56.37 (16)
C2—O1—C3—C44.81 (16)C1—C13—C14—N2−178.76 (11)
C2—N1—C4—C6125.75 (15)C14—C13—C15—C16127.36 (14)
C2—N1—C4—C5−112.49 (15)C1—C13—C15—C16−113.57 (15)
C2—N1—C4—C35.81 (16)C14—C13—C15—C20−53.86 (18)
O1—C3—C4—N1−6.40 (16)C1—C13—C15—C2065.21 (18)
O1—C3—C4—C6−125.16 (14)C20—C15—C16—C17−0.5 (2)
O1—C3—C4—C5109.57 (14)C13—C15—C16—C17178.30 (14)
C1—S1—C7—C875.16 (13)C15—C16—C17—C180.1 (2)
C1—S1—C7—C12−109.45 (12)C16—C17—C18—C190.4 (2)
C12—C7—C8—C9−0.8 (2)C17—C18—C19—C20−0.4 (2)
S1—C7—C8—C9174.58 (11)C18—C19—C20—C150.0 (2)
C7—C8—C9—C10−1.6 (2)C16—C15—C20—C190.4 (2)
C8—C9—C10—C112.1 (2)C13—C15—C20—C19−178.36 (14)
C9—C10—C11—C12−0.3 (2)
D—H···AD—HH···AD···AD—H···A
C14—H14B···O3i0.992.523.376 (2)145
C20—H20···S1ii0.952.793.7194 (19)166
C8—H8···Cg2iii0.952.713.4345 (18)134
C17—H17···Cg3iv0.952.993.712 (2)134
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C7–C12 and C15–C20 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C14—H14B⋯O3i0.992.523.376 (2)145
C20—H20⋯S1ii0.952.793.7194 (19)166
C8—H8⋯Cg2iii0.952.713.4345 (18)134
C17—H17⋯Cg3iv0.952.993.712 (2)134

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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