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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3172.
Published online 2009 November 21. doi:  10.1107/S1600536809049095
PMCID: PMC2971913

rac-2-Iodo-3,4-dihydro­naphthalen-1(2H)-one

Abstract

In the title compound, C10H9IO, the asymmetric unit contains two mol­ecules, in which the iodo-bearing six-membered rings adopt envelope conformations [displacements of the flap atoms = 0.419 (3) and 0.431 (3) Å]. In both mol­ecules, the I atoms are disordered over two set of sites in 0.54 (4):0.46 (4) and 0.71 (3):0.29 (3) ratios. In the crystal, the packing features a weak C—H(...)π inter­action.

Related literature

For a related structure, see: Haddad (1986 [triangle]).

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Object name is e-65-o3172-scheme1.jpg

Experimental

Crystal data

  • C10H9IO
  • M r = 272.07
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3172-efi1.jpg
  • a = 6.115 (5) Å
  • b = 19.658 (4) Å
  • c = 15.896 (5) Å
  • β = 90.551 (5)°
  • V = 1910.7 (17) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 3.31 mm−1
  • T = 296 K
  • 0.28 × 0.20 × 0.18 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.685, T max = 0.717
  • 19043 measured reflections
  • 4397 independent reflections
  • 3632 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.024
  • wR(F 2) = 0.059
  • S = 1.07
  • 4397 reflections
  • 238 parameters
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.50 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049095/hb5236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049095/hb5236Isup2.hkl

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

supplementary crystallographic information

Comment

The title compound (I, Fig. 1) is an intermediate for the total synthesis of steroidal hormones. The ctystal structures of (II) 2,2-Dibromo-3,4-dihydro-1(2H)-naphthalenone (Haddad, 1986) has been published, which seems relavent to (I).

The asymmetric unit of title compound consists of two individual molecules which are clearly racemate. In the molecule having (S)-configuration, the I-atom containing ring A (C1/C6/C7—C10) is twisted with maximum puckering amplitude QT = 0.431 (3) Å, whereas in (R)-configuration the puckering parameter is QT = 0.419 (3) Å. In two molecules the groups of benzene rings along with two adjacent C-atoms, C (C1—C6/C7/C10) and D (C11—C16/C17/C20) are planar with maximum r. m. s. deviations of 0.0114 and 0.0280 Å respectively, from the respective mean square planes. The dihedral angle between C/D is 66.83 (7) Å. In the first molecule the I-atom is disordered over two set of sites having occupancy ratio of 0.54 (4):0.46 (4). Similarly in the other molecule the I-atom is disordered over two set of sites having occupancy ratio of 0.71 (3):0.29 (3). The molecules are stabilized due to C–H···π interactions (Table 1).

Experimental

A solution of I2 (7.75 g, 30.5 mmol) in CHCl3 was added as drops to a solution of 1-tetralone (2.198 g, 15.2 mmol) in acetic acid (9.156 g, 0.1526 mol) and refluxed for 28 h. The H2O (30 ml) was added for partitioning. The reaction mixture was extracted with CHCl3 (3 × 15 ml). The combined organic layer was concentrated in vacuo, the crude was dissolved in ethyl acetate, washed with 5% Na2S2O3 (2 × 15 ml), dried over anhydrous Na2SO4, filtered, boiled with charcoal, concentrated under reduce pressure and allowed for crystallization, which afforded colourless prisms (89%) of (I).

Refinement

The other H-atoms were positioned geometrically (C–H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
View of (I) with the I atoms having greater occupancies. The displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
View of (I) with the I atoms having lesser occupancies. The displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C10H9IOF(000) = 1040
Mr = 272.07Dx = 1.892 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4397 reflections
a = 6.115 (5) Åθ = 2.4–27.8°
b = 19.658 (4) ŵ = 3.31 mm1
c = 15.896 (5) ÅT = 296 K
β = 90.551 (5)°Prism, colourless
V = 1910.7 (17) Å30.28 × 0.20 × 0.18 mm
Z = 8

Data collection

Bruker Kappa APEXII CCD diffractometer4397 independent reflections
Radiation source: fine-focus sealed tube3632 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 7.50 pixels mm-1θmax = 27.8°, θmin = 2.4°
ω scansh = −8→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −25→24
Tmin = 0.685, Tmax = 0.717l = −20→20
19043 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.059w = 1/[σ2(Fo2) + (0.0273P)2 + 0.6672P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
4397 reflectionsΔρmax = 0.39 e Å3
238 parametersΔρmin = −0.49 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00283 (17)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)
I1A0.8199 (5)0.0828 (2)0.36895 (19)0.0502 (6)0.54 (4)
I1B0.8299 (7)0.0783 (3)0.3658 (2)0.0622 (8)0.46 (4)
O10.6627 (3)0.25061 (10)0.31382 (12)0.0512 (6)
C10.9910 (4)0.17057 (12)0.15222 (17)0.0408 (8)
C20.9965 (5)0.16572 (14)0.06450 (19)0.0573 (10)
C30.8386 (6)0.19473 (15)0.01454 (19)0.0637 (10)
C40.6694 (6)0.23029 (15)0.05043 (19)0.0621 (11)
C50.6596 (4)0.23677 (13)0.13679 (17)0.0473 (9)
C60.8181 (3)0.20662 (11)0.18883 (15)0.0350 (7)
C70.8027 (3)0.21515 (11)0.28175 (15)0.0356 (7)
C80.9707 (4)0.17888 (13)0.33563 (17)0.0439 (8)
C91.1881 (4)0.16933 (15)0.2919 (2)0.0546 (9)
C101.1619 (4)0.13632 (14)0.20632 (19)0.0518 (9)
I2A0.2833 (4)0.51127 (14)0.4019 (2)0.0524 (4)0.71 (3)
I2B0.2948 (9)0.5150 (3)0.3949 (5)0.0551 (13)0.29 (3)
O20.1573 (3)0.33920 (10)0.34826 (14)0.0590 (7)
C110.4861 (4)0.42382 (11)0.19085 (17)0.0395 (8)
C120.4975 (5)0.42831 (14)0.1038 (2)0.0593 (11)
C130.3390 (7)0.39932 (18)0.0525 (2)0.0735 (13)
C140.1666 (6)0.36502 (18)0.0870 (2)0.0725 (12)
C150.1531 (4)0.35857 (13)0.1724 (2)0.0528 (10)
C160.3121 (3)0.38740 (11)0.22589 (16)0.0366 (7)
C170.2928 (4)0.37754 (11)0.31794 (16)0.0385 (7)
C180.4509 (4)0.41620 (12)0.37374 (17)0.0431 (8)
C190.6704 (4)0.42740 (14)0.33282 (19)0.0504 (9)
C200.6513 (4)0.45891 (14)0.24640 (19)0.0496 (9)
H21.110500.142150.039430.0687*
H30.845620.19042−0.043640.0763*
H40.561890.249930.016530.0746*
H50.546220.261440.160680.0568*
H80.995190.205360.387100.0527*
H9A1.258100.213270.285370.0654*
H9B1.282680.141260.326860.0654*
H10A1.300980.137650.177570.0620*
H10B1.122100.088950.213800.0620*
H120.613980.451260.079530.0712*
H130.349570.40313−0.005670.0882*
H140.059080.346190.052360.0868*
H150.036790.334710.195470.0632*
H180.472900.390740.426140.0517*
H19A0.758600.456800.368520.0605*
H19B0.745370.384090.328330.0605*
H20A0.610440.506340.252230.0596*
H20B0.793020.457320.219570.0596*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
I1A0.0533 (13)0.0521 (9)0.0453 (9)−0.0069 (5)0.0019 (5)0.0139 (8)
I1B0.084 (2)0.0428 (9)0.0599 (13)−0.0067 (6)0.0130 (10)−0.0018 (11)
O10.0456 (10)0.0531 (11)0.0550 (12)0.0073 (8)0.0063 (8)−0.0161 (9)
C10.0450 (12)0.0273 (12)0.0504 (16)−0.0049 (9)0.0138 (11)0.0004 (11)
C20.0773 (19)0.0391 (15)0.0561 (19)−0.0096 (13)0.0319 (16)−0.0049 (13)
C30.102 (2)0.0490 (17)0.0402 (16)−0.0163 (17)0.0091 (16)0.0025 (14)
C40.083 (2)0.0521 (18)0.0510 (19)−0.0057 (15)−0.0130 (16)0.0118 (14)
C50.0502 (14)0.0387 (14)0.0530 (17)0.0023 (11)−0.0036 (12)0.0000 (12)
C60.0370 (11)0.0243 (11)0.0439 (14)−0.0035 (9)0.0054 (10)−0.0011 (10)
C70.0322 (11)0.0297 (12)0.0448 (14)−0.0045 (9)0.0018 (10)−0.0046 (10)
C80.0442 (13)0.0389 (14)0.0485 (15)−0.0046 (10)−0.0082 (11)−0.0064 (11)
C90.0346 (12)0.0499 (16)0.079 (2)−0.0019 (11)−0.0078 (12)0.0078 (15)
C100.0379 (13)0.0419 (15)0.076 (2)0.0064 (10)0.0160 (13)0.0039 (14)
I2A0.0475 (8)0.0585 (9)0.0512 (5)0.0129 (3)−0.0063 (3)−0.0177 (5)
I2B0.077 (3)0.0322 (19)0.0562 (13)0.0131 (8)0.0055 (13)−0.0043 (12)
O20.0550 (11)0.0514 (12)0.0709 (14)−0.0111 (9)0.0206 (10)0.0053 (10)
C110.0416 (12)0.0274 (12)0.0496 (16)0.0011 (9)0.0093 (11)−0.0039 (10)
C120.0745 (19)0.0488 (17)0.0551 (19)−0.0020 (14)0.0204 (15)0.0010 (14)
C130.105 (3)0.071 (2)0.0446 (18)0.006 (2)0.0004 (18)−0.0078 (16)
C140.086 (2)0.064 (2)0.067 (2)−0.0004 (18)−0.0220 (19)−0.0170 (17)
C150.0511 (15)0.0381 (14)0.069 (2)−0.0081 (11)−0.0073 (13)−0.0075 (13)
C160.0355 (11)0.0259 (12)0.0484 (15)0.0012 (9)0.0025 (10)−0.0033 (10)
C170.0356 (11)0.0283 (12)0.0517 (15)0.0032 (9)0.0071 (10)0.0012 (10)
C180.0445 (13)0.0427 (14)0.0420 (15)0.0102 (10)−0.0023 (11)0.0008 (11)
C190.0341 (12)0.0504 (16)0.0665 (19)0.0033 (10)−0.0068 (12)−0.0087 (13)
C200.0347 (12)0.0433 (15)0.071 (2)−0.0092 (10)0.0103 (12)−0.0039 (13)

Geometric parameters (Å, °)

I1A—C82.170 (5)C9—H9B0.9700
I1B—C82.211 (6)C10—H10A0.9700
I2A—C182.180 (4)C10—H10B0.9700
I2B—C182.192 (7)C11—C121.389 (4)
O1—C71.220 (3)C11—C161.402 (3)
O2—C171.223 (3)C11—C201.503 (4)
C1—C61.404 (3)C12—C131.384 (5)
C1—C21.398 (4)C13—C141.370 (5)
C1—C101.506 (4)C14—C151.367 (5)
C2—C31.369 (5)C15—C161.405 (4)
C3—C41.377 (5)C16—C171.482 (4)
C4—C51.381 (4)C17—C181.511 (4)
C5—C61.400 (4)C18—C191.513 (4)
C6—C71.490 (4)C19—C201.510 (4)
C7—C81.510 (4)C12—H120.9300
C8—C91.518 (4)C13—H130.9300
C9—C101.514 (4)C14—H140.9300
C2—H20.9300C15—H150.9300
C3—H30.9300C18—H180.9800
C4—H40.9300C19—H19A0.9700
C5—H50.9300C19—H19B0.9700
C8—H80.9800C20—H20A0.9700
C9—H9A0.9700C20—H20B0.9700
C2—C1—C6118.2 (2)C12—C11—C16118.3 (2)
C2—C1—C10121.1 (2)C12—C11—C20121.1 (2)
C6—C1—C10120.7 (2)C16—C11—C20120.6 (2)
C1—C2—C3121.8 (3)C11—C12—C13121.3 (3)
C2—C3—C4120.0 (3)C12—C13—C14120.3 (3)
C3—C4—C5119.9 (3)C13—C14—C15119.8 (3)
C4—C5—C6120.8 (2)C14—C15—C16121.0 (3)
C1—C6—C5119.3 (2)C11—C16—C15119.3 (2)
C1—C6—C7121.5 (2)C11—C16—C17121.8 (2)
C5—C6—C7119.21 (19)C15—C16—C17118.9 (2)
O1—C7—C6122.0 (2)O2—C17—C16122.1 (2)
O1—C7—C8120.6 (2)O2—C17—C18120.7 (2)
C6—C7—C8117.38 (18)C16—C17—C18117.2 (2)
I1A—C8—C7105.13 (17)I2A—C18—C17104.62 (17)
I1A—C8—C9112.4 (2)I2A—C18—C19112.60 (18)
I1B—C8—C7106.32 (18)I2B—C18—C17105.0 (2)
I1B—C8—C9109.5 (2)I2B—C18—C19109.1 (2)
C7—C8—C9113.1 (2)C17—C18—C19112.7 (2)
C8—C9—C10112.3 (2)C18—C19—C20112.9 (2)
C1—C10—C9112.9 (2)C11—C20—C19113.1 (2)
C1—C2—H2119.00C11—C12—H12119.00
C3—C2—H2119.00C13—C12—H12119.00
C2—C3—H3120.00C12—C13—H13120.00
C4—C3—H3120.00C14—C13—H13120.00
C3—C4—H4120.00C13—C14—H14120.00
C5—C4—H4120.00C15—C14—H14120.00
C4—C5—H5120.00C14—C15—H15119.00
C6—C5—H5120.00C16—C15—H15119.00
I1A—C8—H8109.00I2A—C18—H18109.00
I1B—C8—H8111.00I2B—C18—H18112.00
C7—C8—H8109.00C17—C18—H18109.00
C9—C8—H8109.00C19—C18—H18109.00
C8—C9—H9A109.00C18—C19—H19A109.00
C8—C9—H9B109.00C18—C19—H19B109.00
C10—C9—H9A109.00C20—C19—H19A109.00
C10—C9—H9B109.00C20—C19—H19B109.00
H9A—C9—H9B108.00H19A—C19—H19B108.00
C1—C10—H10A109.00C11—C20—H20A109.00
C1—C10—H10B109.00C11—C20—H20B109.00
C9—C10—H10A109.00C19—C20—H20A109.00
C9—C10—H10B109.00C19—C20—H20B109.00
H10A—C10—H10B108.00H20A—C20—H20B108.00
C6—C1—C2—C3−0.3 (4)C16—C11—C12—C131.7 (4)
C10—C1—C2—C3177.9 (3)C20—C11—C12—C13−176.3 (3)
C2—C1—C6—C5−0.6 (3)C12—C11—C16—C15−1.8 (3)
C2—C1—C6—C7−178.9 (2)C12—C11—C16—C17177.3 (2)
C10—C1—C6—C5−178.8 (2)C20—C11—C16—C15176.2 (2)
C10—C1—C6—C72.9 (3)C20—C11—C16—C17−4.7 (3)
C2—C1—C10—C9156.0 (2)C12—C11—C20—C19−157.1 (2)
C6—C1—C10—C9−25.8 (3)C16—C11—C20—C1925.0 (3)
C1—C2—C3—C40.5 (5)C11—C12—C13—C14−0.3 (5)
C2—C3—C4—C50.2 (5)C12—C13—C14—C15−1.0 (5)
C3—C4—C5—C6−1.1 (4)C13—C14—C15—C160.9 (5)
C4—C5—C6—C11.3 (4)C14—C15—C16—C110.6 (4)
C4—C5—C6—C7179.6 (2)C14—C15—C16—C17−178.6 (3)
C1—C6—C7—O1174.4 (2)C11—C16—C17—O2−171.0 (2)
C1—C6—C7—C8−4.7 (3)C11—C16—C17—C188.1 (3)
C5—C6—C7—O1−4.0 (3)C15—C16—C17—O28.1 (3)
C5—C6—C7—C8177.1 (2)C15—C16—C17—C18−172.9 (2)
O1—C7—C8—I1A87.3 (2)O2—C17—C18—I2A−89.8 (2)
O1—C7—C8—C9−149.8 (2)O2—C17—C18—C19147.6 (2)
C6—C7—C8—I1A−93.7 (2)C16—C17—C18—I2A91.2 (2)
C6—C7—C8—C929.3 (3)C16—C17—C18—C19−31.5 (3)
I1A—C8—C9—C1066.6 (3)I2A—C18—C19—C20−65.9 (3)
C7—C8—C9—C10−52.2 (3)C17—C18—C19—C2052.1 (3)
C8—C9—C10—C150.1 (3)C18—C19—C20—C11−48.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···Cg30.932.953.700 (4)139

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5236).

References

  • Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
  • Haddad, S. F. (1986). Acta Cryst. C42, 581–584.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

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