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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3236.
Published online 2010 November 20. doi:  10.1107/S1600536810047045
PMCID: PMC3011668

Diethyl [4-(1,3-benzothia­zol-2-yl)benz­yl]phospho­nate

Abstract

In the title mol­ecule, C18H20NO3PS, the benzene ring and the benzothia­zole mean plane are almost coplanar, forming a dihedral angle of 2.29 (2)°. The two ethyl groups are each disordered over two conformations in ratios that refined to 0.59 (1):0.41 (1) and 0.56 (1):0.44 (1). In the crystal, weak inter­molecular C—H(...)O hydrogen bonds link the mol­ecules into layers parallel to the bc plane.

Related literature

For the cardiovascular activity of benzothia­zole-substituted benzyl­phospho­nate derivatives, see: Yoshino et al. (1986 [triangle]). For the crystal structure of a related benzothia­zole-substituted derivative, see: Bhatia et al. (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3236-scheme1.jpg

Experimental

Crystal data

  • C18H20NO3PS
  • M r = 361.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3236-efi1.jpg
  • a = 11.0441 (19) Å
  • b = 8.0927 (14) Å
  • c = 20.933 (4) Å
  • β = 94.943 (3)°
  • V = 1863.9 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 298 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.980, T max = 0.986
  • 11571 measured reflections
  • 3641 independent reflections
  • 2005 reflections with I > 2σ(I)
  • R int = 0.104

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.150
  • S = 0.96
  • 3641 reflections
  • 259 parameters
  • 8 restraints
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810047045/cv2793sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047045/cv2793Isup2.hkl

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

Acknowledgments

The authors are grateful to Xiangfan University for financial support.

supplementary crystallographic information

Comment

It was found that benzothiazole-substituted benzylphosphonates derivatives could exhibit excellent cardiovascular activities (Yoshino et al., 1986). We herein report the structure of the diethyl 4-(benzo[d]thiazol-2-yl)benzylphosphonate (I) (Fig. 1).

In (I), the bond lengths and angles are normal and comparable with those observed in the related compound (Bhatia et al., 1991). The benzene ring and the benzothiazole mean plane are almost coplanar forming a dihedral angle of 2.29 (2)°. Weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to bc plane.

Experimental

The title compound was synthesized according to the method of Yoshino et al. (1986). Crystals suitable for single-crystal X-ray diffraction were grown by slow evaporation of the solution in hexane-MeOH (3:1).

Refinement

All H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined as riding, allowing for free rotation of the methyl groups. The constraint Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) (methyl C) was applied. Two ethyl groups (C15/C16 and C17/C18) were found to be disordered over two orientations. The occupancies of the disordered positions C15/C15', C17/C17' refined to 0.59 (1):0.41 (1) and 0.56 (1):0.44 (1), respectively.

Figures

Fig. 1.
The title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C18H20NO3PSF(000) = 760
Mr = 361.38Dx = 1.288 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1606 reflections
a = 11.0441 (19) Åθ = 2.6–19.8°
b = 8.0927 (14) ŵ = 0.27 mm1
c = 20.933 (4) ÅT = 298 K
β = 94.943 (3)°Block, yellow
V = 1863.9 (6) Å30.20 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer3641 independent reflections
Radiation source: fine-focus sealed tube2005 reflections with I > 2σ(I)
graphiteRint = 0.104
phi and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→13
Tmin = 0.980, Tmax = 0.986k = −9→9
11571 measured reflectionsl = −25→23

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0548P)2] where P = (Fo2 + 2Fc2)/3
3641 reflections(Δ/σ)max = 0.002
259 parametersΔρmax = 0.25 e Å3
8 restraintsΔρmin = −0.20 e Å3

Special details

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)

xyzUiso*/UeqOcc. (<1)
C11.1588 (3)0.1221 (4)0.69500 (17)0.0623 (10)
C21.2308 (3)0.2279 (4)0.73429 (17)0.0595 (9)
C31.3327 (4)0.2969 (5)0.7108 (2)0.0774 (11)
H31.38220.36820.73630.093*
C41.3602 (4)0.2599 (5)0.6504 (2)0.0840 (12)
H41.42860.30740.63500.101*
C51.2893 (4)0.1538 (5)0.6113 (2)0.0865 (12)
H51.31030.13070.57020.104*
C61.1881 (4)0.0827 (5)0.63310 (19)0.0811 (12)
H61.14010.01010.60740.097*
C71.0931 (3)0.1737 (4)0.80139 (17)0.0566 (9)
C81.0286 (3)0.1760 (4)0.85962 (17)0.0550 (9)
C90.9251 (3)0.0812 (4)0.86477 (18)0.0681 (10)
H90.89410.01770.83010.082*
C100.8674 (3)0.0802 (4)0.9212 (2)0.0705 (10)
H100.79800.01620.92370.085*
C110.9113 (3)0.1726 (4)0.97371 (18)0.0609 (9)
C121.0131 (3)0.2685 (4)0.96797 (18)0.0639 (10)
H121.04320.33341.00240.077*
C131.0714 (3)0.2703 (4)0.91201 (18)0.0624 (9)
H131.14010.33560.90960.075*
C140.8502 (3)0.1645 (5)1.03566 (18)0.0743 (11)
H14A0.90760.20201.07030.089*
H14B0.83130.04991.04410.089*
C150.5008 (10)0.2379 (17)0.9677 (8)0.080 (4)0.59 (1)
H15A0.48580.34960.98190.096*0.59 (1)
H15B0.44210.16450.98480.096*0.59 (1)
C160.491 (2)0.229 (3)0.8963 (9)0.127 (7)0.59 (1)
H16A0.55360.29690.88030.191*0.59 (1)
H16B0.41300.26900.87950.191*0.59 (1)
H16C0.50150.11710.88300.191*0.59 (1)
C170.6829 (11)0.3458 (18)1.1595 (6)0.081 (4)0.56 (1)
H17A0.61310.41651.16370.098*0.56 (1)
H17B0.75500.41371.15820.098*0.56 (1)
C180.698 (2)0.221 (3)1.2130 (9)0.102 (7)0.56 (1)
H18A0.62020.17311.21930.152*0.56 (1)
H18B0.72920.27541.25180.152*0.56 (1)
H18C0.75300.13651.20220.152*0.56 (1)
C15'0.5313 (16)0.286 (3)0.9542 (13)0.095 (7)0.41 (1)
H15C0.56860.36790.92810.114*0.41 (1)
H15D0.48360.34390.98400.114*0.41 (1)
C16'0.453 (3)0.175 (4)0.9131 (15)0.114 (9)0.41 (1)
H16D0.48930.15470.87380.171*0.41 (1)
H16E0.37450.22480.90370.171*0.41 (1)
H16F0.44360.07180.93500.171*0.41 (1)
C17'0.7377 (13)0.300 (3)1.1609 (8)0.084 (5)0.44 (1)
H17C0.75140.41811.15650.101*0.44 (1)
H17D0.81620.24611.16380.101*0.44 (1)
C18'0.679 (3)0.271 (4)1.2219 (12)0.091 (8)0.44 (1)
H18D0.59410.29681.21550.137*0.44 (1)
H18E0.71690.33921.25530.137*0.44 (1)
H18F0.68860.15661.23400.137*0.44 (1)
N11.1913 (2)0.2556 (3)0.79452 (14)0.0638 (8)
O10.7282 (2)0.4580 (3)1.02534 (11)0.0758 (7)
O30.6649 (2)0.2406 (3)1.10323 (12)0.0780 (8)
O20.6244 (2)0.1867 (3)0.98898 (12)0.0767 (8)
P10.71450 (8)0.28288 (12)1.03709 (5)0.0610 (3)
S11.03702 (9)0.05586 (12)0.73533 (5)0.0754 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.057 (2)0.065 (2)0.062 (2)0.0036 (18)−0.0136 (18)−0.0071 (19)
C20.049 (2)0.072 (2)0.056 (2)0.0097 (18)−0.0021 (18)−0.0063 (19)
C30.061 (3)0.095 (3)0.075 (3)0.002 (2)0.000 (2)−0.020 (2)
C40.066 (3)0.105 (3)0.082 (3)0.012 (2)0.009 (2)−0.012 (3)
C50.097 (3)0.096 (3)0.066 (3)0.016 (3)0.005 (3)−0.009 (2)
C60.096 (3)0.085 (3)0.058 (3)0.004 (2)−0.012 (2)−0.015 (2)
C70.047 (2)0.055 (2)0.066 (2)0.0101 (17)−0.0098 (18)−0.0057 (17)
C80.0395 (19)0.055 (2)0.068 (2)0.0065 (16)−0.0079 (17)−0.0057 (18)
C90.058 (2)0.074 (3)0.070 (3)−0.0026 (19)−0.008 (2)−0.014 (2)
C100.045 (2)0.077 (3)0.087 (3)−0.0060 (18)−0.006 (2)0.000 (2)
C110.046 (2)0.067 (2)0.069 (3)0.0102 (18)−0.0033 (19)0.006 (2)
C120.055 (2)0.069 (2)0.066 (2)0.0032 (19)−0.0060 (19)−0.0095 (19)
C130.048 (2)0.060 (2)0.078 (3)−0.0030 (17)−0.0071 (19)−0.007 (2)
C140.060 (2)0.085 (3)0.076 (3)0.010 (2)−0.005 (2)0.015 (2)
C150.038 (6)0.082 (7)0.119 (10)−0.003 (5)0.000 (6)−0.027 (7)
C160.136 (18)0.147 (19)0.090 (9)0.005 (9)−0.043 (10)−0.011 (9)
C170.089 (10)0.092 (8)0.065 (7)−0.006 (7)0.014 (7)−0.008 (5)
C180.111 (11)0.116 (14)0.072 (11)0.034 (8)−0.022 (9)0.001 (9)
C15'0.047 (10)0.119 (16)0.117 (17)−0.015 (8)−0.010 (10)−0.007 (10)
C16'0.081 (14)0.109 (16)0.14 (2)0.002 (10)−0.043 (14)−0.013 (14)
C17'0.067 (11)0.113 (14)0.074 (9)−0.014 (9)0.016 (8)−0.021 (9)
C18'0.088 (13)0.110 (18)0.075 (11)−0.012 (13)0.005 (8)−0.016 (10)
N10.0427 (18)0.077 (2)0.070 (2)0.0028 (15)−0.0056 (15)−0.0137 (16)
O10.0827 (18)0.0666 (16)0.0759 (17)−0.0010 (13)−0.0063 (14)0.0039 (13)
O30.0760 (18)0.0861 (18)0.0732 (17)−0.0192 (13)0.0138 (14)−0.0070 (15)
O20.0601 (16)0.0811 (17)0.0856 (18)0.0031 (13)−0.0133 (14)−0.0165 (14)
P10.0519 (6)0.0678 (7)0.0622 (6)−0.0007 (5)−0.0016 (5)0.0004 (5)
S10.0690 (7)0.0816 (7)0.0724 (7)−0.0100 (5)−0.0119 (5)−0.0187 (5)

Geometric parameters (Å, °)

C1—C21.389 (5)C15—C161.492 (15)
C1—C61.399 (5)C15—H15A0.9700
C1—S11.734 (4)C15—H15B0.9700
C2—C31.384 (5)C16—H16A0.9600
C2—N11.388 (4)C16—H16B0.9600
C3—C41.359 (5)C16—H16C0.9600
C3—H30.9300C17—O31.454 (11)
C4—C51.383 (5)C17—C181.504 (16)
C4—H40.9300C17—H17A0.9700
C5—C61.370 (5)C17—H17B0.9700
C5—H50.9300C18—H18A0.9600
C6—H60.9300C18—H18B0.9600
C7—N11.289 (4)C18—H18C0.9600
C7—C81.464 (5)C15'—O21.452 (16)
C7—S11.749 (3)C15'—C16'1.477 (18)
C8—C131.385 (4)C15'—H15C0.9700
C8—C91.389 (5)C15'—H15D0.9700
C9—C101.390 (5)C16'—H16D0.9600
C9—H90.9300C16'—H16E0.9600
C10—C111.382 (5)C16'—H16F0.9600
C10—H100.9300C17'—O31.474 (14)
C11—C121.380 (5)C17'—C18'1.501 (17)
C11—C141.514 (5)C17'—H17C0.9700
C12—C131.385 (5)C17'—H17D0.9700
C12—H120.9300C18'—H18D0.9600
C13—H130.9300C18'—H18E0.9600
C14—P11.781 (3)C18'—H18F0.9600
C14—H14A0.9700O1—P11.448 (2)
C14—H14B0.9700O3—P11.570 (3)
C15—O21.459 (11)O2—P11.561 (2)
C2—C1—C6121.5 (4)O2—C15—H15B110.5
C2—C1—S1109.3 (3)C16—C15—H15B110.5
C6—C1—S1129.2 (3)H15A—C15—H15B108.7
C3—C2—N1125.9 (3)O3—C17—C18102.1 (13)
C3—C2—C1118.7 (4)O3—C17—H17A111.3
N1—C2—C1115.4 (3)C18—C17—H17A111.3
C4—C3—C2119.7 (4)O3—C17—H17B111.3
C4—C3—H3120.2C18—C17—H17B111.3
C2—C3—H3120.2H17A—C17—H17B109.2
C3—C4—C5121.8 (4)O2—C15'—C16'107.9 (19)
C3—C4—H4119.1O2—C15'—H15C110.1
C5—C4—H4119.1C16'—C15'—H15C110.1
C6—C5—C4120.0 (4)O2—C15'—H15D110.1
C6—C5—H5120.0C16'—C15'—H15D110.1
C4—C5—H5120.0H15C—C15'—H15D108.4
C5—C6—C1118.2 (4)C15'—C16'—H16D109.5
C5—C6—H6120.9C15'—C16'—H16E109.5
C1—C6—H6120.9H16D—C16'—H16E109.5
N1—C7—C8124.1 (3)C15'—C16'—H16F109.5
N1—C7—S1115.8 (3)H16D—C16'—H16F109.5
C8—C7—S1120.0 (3)H16E—C16'—H16F109.5
C13—C8—C9118.0 (4)O3—C17'—C18'113.6 (17)
C13—C8—C7120.6 (3)O3—C17'—H17C108.8
C9—C8—C7121.4 (3)C18'—C17'—H17C108.8
C8—C9—C10120.7 (3)O3—C17'—H17D108.8
C8—C9—H9119.7C18'—C17'—H17D108.9
C10—C9—H9119.7H17C—C17'—H17D107.7
C11—C10—C9121.2 (3)C17'—C18'—H18D109.5
C11—C10—H10119.4C17'—C18'—H18E109.5
C9—C10—H10119.4H18D—C18'—H18E109.5
C12—C11—C10117.9 (4)C17'—C18'—H18F109.5
C12—C11—C14121.7 (3)H18D—C18'—H18F109.5
C10—C11—C14120.4 (3)H18E—C18'—H18F109.5
C11—C12—C13121.4 (3)C7—N1—C2110.6 (3)
C11—C12—H12119.3C17—O3—C17'27.9 (6)
C13—C12—H12119.3C17—O3—P1123.6 (7)
C12—C13—C8120.8 (3)C17'—O3—P1116.4 (8)
C12—C13—H13119.6C15'—O2—C1523.9 (10)
C8—C13—H13119.6C15'—O2—P1115.5 (10)
C11—C14—P1115.4 (2)C15—O2—P1125.6 (7)
C11—C14—H14A108.4O1—P1—O2116.64 (14)
P1—C14—H14A108.4O1—P1—O3114.38 (15)
C11—C14—H14B108.4O2—P1—O3102.06 (14)
P1—C14—H14B108.4O1—P1—C14115.01 (17)
H14A—C14—H14B107.5O2—P1—C14102.21 (16)
O2—C15—C16106.0 (13)O3—P1—C14104.79 (16)
O2—C15—H15A110.5C1—S1—C788.84 (18)
C16—C15—H15A110.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.453.261 (5)146
C13—H13···O1ii0.932.533.310 (4)141

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2793).

References

  • Bhatia, S. C., Kumar, A., Gautam, P. & Jain, P. C. (1991). Acta Cryst. C47, 1908–1911.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yoshino, K., Kohno, T., Uno, T., Morita, T. & Tsukamoto, G. (1986). J. Med. Chem.29, 820–825. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography