Literature DB >> 21754101

4-Hy-droxy-6-(4-meth-oxy-phen-yl)-4-phenyl-1,3-diazinane-2-thione.

H C Devarajegowda, K R Roopashree, Irfan Ali Mohammed, Ravish Sankolli.   

Abstract

In the title compound, C(17)H(18)N(2)O(2)S, the 1,3-diazinane-2-thione ring system is not coplanar with the benzene ring and meth-oxy-phenyl ring system, the dihedral angle between the planes being 65.58 (13) and 89.18 (10)°, respectively. The crystal structure is characterized by inter-molecular O-H⋯S, N-H⋯S, N-H⋯O and C-H⋯S hydrogen bonding.

Entities:  

Year:  2011        PMID： 21754101      PMCID： PMC3099814          DOI： 10.1107/S1600536811008002

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


Related literature

For general background to pyrimidines, see: Cheng (1969 ▶); Scott et al. (1959 ▶); Jonak et al. (1972 ▶); Falco et al. (1961 ▶); Ram (1990 ▶); Howells et al. (1981 ▶); Pershin et al. (1972 ▶); Matolcsy (1971 ▶); Prikazchikova et al. (1975 ▶). For the synthesis, see: Paghdar et al. (2007 ▶). For a related structure, see: Yamin et al. (2005 ▶).

Experimental

Crystal data

C17H18N2O2S M = 314.39 Monoclinic, a = 12.6016 (3) Å b = 6.3375 (1) Å c = 20.6637 (4) Å β = 97.890 (2)° V = 1634.64 (6) Å3 Z = 4 Mo Kα radiation μ = 0.21 mm−1 T = 295 K 0.18 × 0.16 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur diffractometer Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 ▶) T min = 0.963, T max = 1.000 18135 measured reflections 3547 independent reflections 2566 reflections with I > 2σ(I) R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.045 wR(F 2) = 0.115 S = 1.08 3547 reflections 215 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.24 e Å−3 Δρmin = −0.17 e Å−3 Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008002/bv2177sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008002/bv2177Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H18N2O2SF(000) = 664
Mr = 314.39Dx = 1.278 Mg m−3
Monoclinic, P21/cMelting point: 392 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.6016 (3) ÅCell parameters from 3547 reflections
b = 6.3375 (1) Åθ = 2.4–27.0°
c = 20.6637 (4) ŵ = 0.21 mm−1
β = 97.890 (2)°T = 295 K
V = 1634.64 (6) Å3Plate, colourless
Z = 40.18 × 0.16 × 0.16 mm
Oxford Diffraction Xcalibur diffractometer3547 independent reflections
Radiation source: Enhance (Mo) X-ray Source2566 reflections with I > 2σ(I)
graphiteRint = 0.039
Detector resolution: 16.0839 pixels mm-1θmax = 27.0°, θmin = 2.4°
ω scansh = −16→16
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010)k = −8→7
Tmin = 0.963, Tmax = 1.000l = −26→26
18135 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0447P)2 + 0.3347P] where P = (Fo2 + 2Fc2)/3
3547 reflections(Δ/σ)max < 0.001
215 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05–01–2010 CrysAlis171. NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
S10.48694 (4)0.81337 (8)0.41473 (2)0.04465 (17)
O20.28051 (14)0.2485 (2)0.48527 (8)0.0550 (4)
O30.32640 (13)1.1217 (2)0.79728 (7)0.0595 (4)
N40.40048 (13)0.7486 (3)0.52278 (7)0.0431 (4)
H40.44300.84700.53900.052*
N50.32830 (12)0.5582 (2)0.43340 (7)0.0430 (4)
H50.33100.52430.39340.052*
C60.08485 (19)0.2493 (4)0.41656 (13)0.0669 (7)
H60.10740.13900.44480.080*
C7−0.0087 (2)0.2288 (5)0.37313 (17)0.0873 (9)
H7−0.04790.10440.37250.105*
C8−0.0434 (2)0.3852 (7)0.33198 (16)0.0943 (10)
H8−0.10610.36900.30290.113*
C90.0139 (2)0.5698 (6)0.33308 (15)0.0935 (9)
H9−0.01010.67930.30490.112*
C100.1081 (2)0.5928 (4)0.37639 (13)0.0715 (7)
H100.14660.71820.37700.086*
C110.14488 (16)0.4324 (3)0.41824 (10)0.0464 (5)
C120.24682 (15)0.4557 (3)0.46603 (9)0.0423 (5)
C130.22823 (17)0.5908 (4)0.52483 (10)0.0474 (5)
C140.33350 (16)0.6441 (3)0.56604 (9)0.0421 (5)
C150.39945 (14)0.7009 (3)0.46044 (9)0.0369 (4)
C160.32722 (15)0.7792 (3)0.62573 (9)0.0397 (4)
C170.27293 (16)0.9682 (3)0.62387 (9)0.0454 (5)
H170.23721.01620.58420.055*
C180.27031 (16)1.0888 (3)0.67978 (9)0.0456 (5)
H180.23291.21570.67760.055*
C190.32394 (16)1.0182 (3)0.73856 (9)0.0442 (5)
C200.38044 (19)0.8316 (4)0.74086 (10)0.0568 (6)
H200.41750.78490.78030.068*
C210.38211 (18)0.7138 (3)0.68487 (10)0.0521 (5)
H210.42080.58850.68690.063*
C220.2770 (3)1.3220 (4)0.79812 (12)0.0780 (8)
H22A0.28511.37470.84210.117*
H22B0.20221.30930.78180.117*
H22C0.31011.41790.77100.117*
H20.345 (2)0.244 (4)0.5073 (14)0.081 (9)*
H13A0.1920 (17)0.726 (3)0.5100 (10)0.054 (6)*
H13B0.1841 (16)0.512 (3)0.5504 (10)0.054 (6)*
H140.3700 (14)0.504 (3)0.5815 (9)0.045 (5)*
U11U22U33U12U13U23
S10.0494 (3)0.0552 (3)0.0309 (3)−0.0148 (2)0.0107 (2)−0.0048 (2)
O20.0585 (10)0.0531 (9)0.0499 (9)−0.0108 (8)−0.0050 (8)0.0045 (7)
O30.0839 (11)0.0644 (10)0.0302 (7)0.0027 (8)0.0081 (7)−0.0087 (7)
N40.0473 (9)0.0555 (10)0.0274 (8)−0.0184 (8)0.0085 (7)−0.0080 (7)
N50.0476 (9)0.0550 (10)0.0273 (8)−0.0169 (8)0.0091 (7)−0.0080 (7)
C60.0521 (14)0.0733 (16)0.0741 (17)−0.0193 (12)0.0038 (12)−0.0066 (13)
C70.0505 (16)0.109 (2)0.099 (2)−0.0249 (16)−0.0020 (16)−0.028 (2)
C80.0495 (16)0.148 (3)0.079 (2)−0.002 (2)−0.0135 (14)−0.032 (2)
C90.0699 (19)0.129 (3)0.074 (2)0.0122 (19)−0.0166 (15)0.0102 (19)
C100.0617 (15)0.0838 (17)0.0648 (17)−0.0053 (14)−0.0065 (13)0.0077 (14)
C110.0424 (11)0.0614 (13)0.0356 (10)−0.0074 (10)0.0068 (9)−0.0083 (9)
C120.0442 (11)0.0490 (11)0.0338 (10)−0.0113 (9)0.0061 (8)−0.0011 (9)
C130.0492 (12)0.0613 (14)0.0335 (11)−0.0173 (11)0.0122 (9)−0.0069 (10)
C140.0493 (11)0.0496 (12)0.0278 (10)−0.0084 (10)0.0072 (8)−0.0008 (8)
C150.0373 (10)0.0436 (10)0.0293 (9)−0.0026 (8)0.0028 (8)−0.0008 (8)
C160.0418 (10)0.0504 (11)0.0276 (9)−0.0110 (9)0.0076 (8)−0.0007 (8)
C170.0509 (12)0.0593 (13)0.0251 (9)−0.0048 (10)0.0015 (8)0.0054 (9)
C180.0528 (12)0.0487 (11)0.0362 (11)−0.0010 (10)0.0093 (9)0.0011 (9)
C190.0541 (12)0.0522 (12)0.0273 (9)−0.0091 (10)0.0091 (9)−0.0020 (8)
C200.0732 (15)0.0646 (14)0.0294 (11)0.0062 (12)−0.0038 (10)0.0006 (10)
C210.0633 (14)0.0564 (13)0.0352 (11)0.0064 (11)0.0016 (10)−0.0011 (9)
C220.134 (3)0.0563 (15)0.0468 (14)−0.0004 (15)0.0242 (15)−0.0084 (11)
S1—C151.7033 (18)C10—H100.9300
O2—C121.420 (2)C11—C121.516 (3)
O2—H20.87 (3)C12—C131.531 (3)
O3—C191.376 (2)C13—C141.513 (3)
O3—C221.415 (3)C13—H13A1.00 (2)
N4—C151.321 (2)C13—H13B0.96 (2)
N4—C141.469 (2)C14—C161.513 (3)
N4—H40.8600C14—H141.029 (19)
N5—C151.340 (2)C16—C171.377 (3)
N5—C121.456 (2)C16—C211.382 (3)
N5—H50.8600C17—C181.390 (3)
C6—C111.383 (3)C17—H170.9300
C6—C71.386 (4)C18—C191.381 (3)
C6—H60.9300C18—H180.9300
C7—C81.340 (4)C19—C201.378 (3)
C7—H70.9300C20—C211.379 (3)
C8—C91.374 (5)C20—H200.9300
C8—H80.9300C21—H210.9300
C9—C101.393 (4)C22—H22A0.9600
C9—H90.9300C22—H22B0.9600
C10—C111.373 (3)C22—H22C0.9600
C12—O2—H2113.2 (17)C12—C13—H13B108.1 (12)
C19—O3—C22118.80 (17)H13A—C13—H13B109.9 (17)
C15—N4—C14124.10 (16)N4—C14—C16109.86 (15)
C15—N4—H4117.9N4—C14—C13106.90 (16)
C14—N4—H4117.9C16—C14—C13116.45 (17)
C15—N5—C12125.57 (15)N4—C14—H14107.9 (10)
C15—N5—H5117.2C16—C14—H14107.9 (11)
C12—N5—H5117.2C13—C14—H14107.6 (11)
C11—C6—C7120.6 (3)N4—C15—N5118.50 (16)
C11—C6—H6119.7N4—C15—S1121.63 (14)
C7—C6—H6119.7N5—C15—S1119.87 (13)
C8—C7—C6121.1 (3)C17—C16—C21118.15 (18)
C8—C7—H7119.4C17—C16—C14123.44 (17)
C6—C7—H7119.4C21—C16—C14118.37 (19)
C7—C8—C9119.6 (3)C16—C17—C18121.58 (18)
C7—C8—H8120.2C16—C17—H17119.2
C9—C8—H8120.2C18—C17—H17119.2
C8—C9—C10120.0 (3)C19—C18—C17119.23 (19)
C8—C9—H9120.0C19—C18—H18120.4
C10—C9—H9120.0C17—C18—H18120.4
C11—C10—C9120.7 (3)O3—C19—C20115.45 (18)
C11—C10—H10119.6O3—C19—C18124.77 (19)
C9—C10—H10119.6C20—C19—C18119.79 (18)
C10—C11—C6118.0 (2)C19—C20—C21120.2 (2)
C10—C11—C12121.35 (19)C19—C20—H20119.9
C6—C11—C12120.7 (2)C21—C20—H20119.9
O2—C12—N5109.84 (16)C20—C21—C16121.1 (2)
O2—C12—C11106.63 (16)C20—C21—H21119.5
N5—C12—C11109.27 (15)C16—C21—H21119.5
O2—C12—C13111.57 (17)O3—C22—H22A109.5
N5—C12—C13108.21 (15)O3—C22—H22B109.5
C11—C12—C13111.30 (16)H22A—C22—H22B109.5
C14—C13—C12110.72 (17)O3—C22—H22C109.5
C14—C13—H13A108.1 (12)H22A—C22—H22C109.5
C12—C13—H13A110.4 (12)H22B—C22—H22C109.5
C14—C13—H13B109.6 (12)
C11—C6—C7—C8−0.2 (4)C12—C13—C14—N456.3 (2)
C6—C7—C8—C9−0.5 (5)C12—C13—C14—C16179.46 (17)
C7—C8—C9—C100.5 (5)C14—N4—C15—N54.5 (3)
C8—C9—C10—C110.1 (4)C14—N4—C15—S1−174.57 (15)
C9—C10—C11—C6−0.8 (4)C12—N5—C15—N43.2 (3)
C9—C10—C11—C12−179.5 (2)C12—N5—C15—S1−177.72 (15)
C7—C6—C11—C100.9 (4)N4—C14—C16—C1769.8 (2)
C7—C6—C11—C12179.6 (2)C13—C14—C16—C17−51.9 (3)
C15—N5—C12—O2−101.5 (2)N4—C14—C16—C21−107.7 (2)
C15—N5—C12—C11141.84 (19)C13—C14—C16—C21130.6 (2)
C15—N5—C12—C1320.5 (3)C21—C16—C17—C18−1.7 (3)
C10—C11—C12—O2−161.1 (2)C14—C16—C17—C18−179.17 (18)
C6—C11—C12—O220.3 (2)C16—C17—C18—C190.4 (3)
C10—C11—C12—N5−42.4 (3)C22—O3—C19—C20175.4 (2)
C6—C11—C12—N5138.9 (2)C22—O3—C19—C18−4.4 (3)
C10—C11—C12—C1377.0 (3)C17—C18—C19—O3−179.22 (18)
C6—C11—C12—C13−101.6 (2)C17—C18—C19—C201.0 (3)
O2—C12—C13—C1470.8 (2)O3—C19—C20—C21179.17 (19)
N5—C12—C13—C14−50.2 (2)C18—C19—C20—C21−1.0 (3)
C11—C12—C13—C14−170.27 (18)C19—C20—C21—C16−0.3 (3)
C15—N4—C14—C16−161.66 (18)C17—C16—C21—C201.6 (3)
C15—N4—C14—C13−34.5 (3)C14—C16—C21—C20179.26 (19)
D—H···AD—HH···AD···AD—H···A
O2—H2···S1i0.88 (3)2.51 (3)3.3688 (18)169 (2)
C14—H14···S1i1.030 (19)2.695 (18)3.666 (2)157.0 (14)
N4—H4···S1ii0.862.473.2990 (19)163
N5—H5···O3iii0.862.183.032 (2)169
C20—H20···S1iv0.932.863.772 (2)166
C6—H6···O20.932.332.671 (3)101
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O2—H2⋯S1i0.88 (3)2.51 (3)3.3688 (18)169 (2)
C14—H14⋯S1i1.030 (19)2.695 (18)3.666 (2)157.0 (14)
N4—H4⋯S1ii0.862.473.2990 (19)163
N5—H5⋯O3iii0.862.183.032 (2)169
C20—H20⋯S1iv0.932.863.772 (2)166

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

  7 in total

1.  Effect of substituted pyrimidines on growth and biosynthesis of microorganisms.

Authors:  D B M SCOTT; T L ULBRICHT; M L ROGERS; E CHU; C ROSE
Journal:  Cancer Res       Date:  1959-04       Impact factor: 12.701

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 3.  Some pyrimidines of biological and medicinal interest. I.

Authors:  C C Cheng
Journal:  Prog Med Chem       Date:  1969

4.  Synthesis and biological activity of some 5-substituted 2,4-diamino-6-alkylpyrimidines. 3.

Authors:  J P Jonak; S F Zakrzewski; L H Mead
Journal:  J Med Chem       Date:  1972-06       Impact factor: 7.446

5.  [Antibacterial activity of pyrimidine and pyrrolo-(3,2-d)-pyrimidine derivatives].

Authors:  G N Pershin; L I Shcherbakova; T N Zykova; V N Sokolova
Journal:  Farmakol Toksikol       Date:  1972-07

6.  Chemotherapeutic agents, XVIII: Synthesis of pi-deficient pyrimidines and fused pyrimidines as leishmanicidal agents.

Authors:  V J Ram
Journal:  Arch Pharm (Weinheim)       Date:  1990-11       Impact factor: 3.751

7.  The effect of 5-fluorouracil and 5-fluorocytosine on the development of the filarial nematodes Brugia pahangi and Dirofilaria immitis.

Authors:  R E Howells; J Tinsley; E Devaney; G Smith
Journal:  Acta Trop       Date:  1981-09       Impact factor: 3.112
  7 in total

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