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

organic compounds Acta Crystallographica Section E Mo K radiation  = 3.31 mm 1 T = 296 K 0.28  0.20  0.18 mm b = 19.658 (4) Å c = 15.896 (5) Å = 90.551 (5) V = 1910.7 (17) Å3 Z=8 Structure Reports Online ISSN 1600-5368 Data collection rac-2-Iodo-3,4-dihydronaphthalen1(2H)-one Abdul Rauf Raza,a M. Nawaz Tahir,b* Ayesha Sultan,a Muhammad Danisha and Muhammad Sohaila a Department of Chemistry, University of Sargodha, Sargodha, Pakistan, and b Department of Physics, University of Sargodha, Sargodha, Pakistan Correspondence e-mail: [email protected] Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.685, Tmax = 0.717 19043 measured reflections 4397 independent reflections 3632 reflections with I > 2(I) Rint = 0.026 Refinement R[F 2 > 2(F 2)] = 0.024 wR(F 2) = 0.059 S = 1.07 4397 reflections 238 parameters H-atom parameters constrained
max = 0.39 e Å 3
min = 0.50 e Å 3 Received 17 November 2009; accepted 18 November 2009 Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.004 Å; disorder in main residue; R factor = 0.024; wR factor = 0.059; data-to-parameter ratio = 18.5. 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


 interaction. Table 1 Hydrogen-bond geometry (Å,  ). D—H


A D—H H


A D


A D—H


A C5—H5


Cg3 0.93 2.95 3.700 (4) 139 Cg3 is the centroid of the C11–C16 ring. Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON. Related literature For a related structure, see: Haddad (1986). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5236). References Experimental Crystal data Monoclinic, P21 =c a = 6.115 (5) Å C10H9IO Mr = 272.07 o3172 Raza et al. 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. Spek, A. L. (2009). Acta Cryst. D65, 148–155. doi:10.1107/S1600536809049095 Acta Cryst. (2009). E65, o3172 supporting information supporting information Acta Cryst. (2009). E65, o3172 [doi:10.1107/S1600536809049095] rac-2-Iodo-3,4-dihydronaphthalen-1(2H)-one Abdul Rauf Raza, M. Nawaz Tahir, Ayesha Sultan, Muhammad Danish and Muhammad Sohail S1. 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). S2. 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). S3. 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). Acta Cryst. (2009). E65, o3172 sup-1 supporting information Figure 1 View of (I) with the I atoms having greater occupancies. The displacement ellipsoids are drawn at the 30% probability level. Acta Cryst. (2009). E65, o3172 sup-2 supporting information Figure 2 View of (I) with the I atoms having lesser occupancies. The displacement ellipsoids are drawn at the 30% probability level. rac-2-Iodo-3,4-dihydronaphthalen-1(2H)-one Crystal data C10H9IO Mr = 272.07 Monoclinic, P21/c Hall symbol: -P 2ybc 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 F(000) = 1040 Dx = 1.892 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4397 reflections θ = 2.4–27.8° µ = 3.31 mm−1 T = 296 K Prism, colourless 0.28 × 0.20 × 0.18 mm Data collection Bruker Kappa APEXII CCD diffractometer Radiation source: fine-focus sealed tube Graphite monochromator Detector resolution: 7.50 pixels mm-1 ω scans Absorption correction: multi-scan (SADABS; Bruker, 2005) Tmin = 0.685, Tmax = 0.717 Acta Cryst. (2009). E65, o3172 19043 measured reflections 4397 independent reflections 3632 reflections with I > 2σ(I) Rint = 0.026 θmax = 27.8°, θmin = 2.4° h = −8→7 k = −25→24 l = −20→20 sup-3 supporting information Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.024 wR(F2) = 0.059 S = 1.07 4397 reflections 238 parameters 0 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0273P)2 + 0.6672P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.002 Δρmax = 0.39 e Å−3 Δρmin = −0.50 e Å−3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction 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) I1A I1B O1 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 I2A I2B O2 C11 C12 C13 C14 C15 C16 C17 C18 x y z Uiso*/Ueq Occ. (<1) 0.8199 (5) 0.8299 (7) 0.6627 (3) 0.9910 (4) 0.9965 (5) 0.8386 (6) 0.6694 (6) 0.6596 (4) 0.8181 (3) 0.8027 (3) 0.9707 (4) 1.1881 (4) 1.1619 (4) 0.2833 (4) 0.2948 (9) 0.1573 (3) 0.4861 (4) 0.4975 (5) 0.3390 (7) 0.1666 (6) 0.1531 (4) 0.3121 (3) 0.2928 (4) 0.4509 (4) 0.0828 (2) 0.0783 (3) 0.25061 (10) 0.17057 (12) 0.16572 (14) 0.19473 (15) 0.23029 (15) 0.23677 (13) 0.20662 (11) 0.21515 (11) 0.17888 (13) 0.16933 (15) 0.13632 (14) 0.51127 (14) 0.5150 (3) 0.33920 (10) 0.42382 (11) 0.42831 (14) 0.39932 (18) 0.36502 (18) 0.35857 (13) 0.38740 (11) 0.37754 (11) 0.41620 (12) 0.36895 (19) 0.3658 (2) 0.31382 (12) 0.15222 (17) 0.06450 (19) 0.01454 (19) 0.05043 (19) 0.13679 (17) 0.18883 (15) 0.28175 (15) 0.33563 (17) 0.2919 (2) 0.20632 (19) 0.4019 (2) 0.3949 (5) 0.34826 (14) 0.19085 (17) 0.1038 (2) 0.0525 (2) 0.0870 (2) 0.1724 (2) 0.22589 (16) 0.31794 (16) 0.37374 (17) 0.0502 (6) 0.0622 (8) 0.0512 (6) 0.0408 (8) 0.0573 (10) 0.0637 (10) 0.0621 (11) 0.0473 (9) 0.0350 (7) 0.0356 (7) 0.0439 (8) 0.0546 (9) 0.0518 (9) 0.0524 (4) 0.0551 (13) 0.0590 (7) 0.0395 (8) 0.0593 (11) 0.0735 (13) 0.0725 (12) 0.0528 (10) 0.0366 (7) 0.0385 (7) 0.0431 (8) 0.54 (4) 0.46 (4) Acta Cryst. (2009). E65, o3172 0.71 (3) 0.29 (3) sup-4 supporting information C19 C20 H2 H3 H4 H5 H8 H9A H9B H10A H10B H12 H13 H14 H15 H18 H19A H19B H20A H20B 0.6704 (4) 0.6513 (4) 1.11050 0.84562 0.56189 0.54622 0.99519 1.25810 1.28268 1.30098 1.12210 0.61398 0.34957 0.05908 0.03679 0.47290 0.75860 0.74537 0.61044 0.79302 0.42740 (14) 0.45891 (14) 0.14215 0.19042 0.24993 0.26144 0.20536 0.21327 0.14126 0.13765 0.08895 0.45126 0.40313 0.34619 0.33471 0.39074 0.45680 0.38409 0.50634 0.45732 0.33282 (19) 0.24640 (19) 0.03943 −0.04364 0.01653 0.16068 0.38710 0.28537 0.32686 0.17757 0.21380 0.07953 −0.00567 0.05236 0.19547 0.42614 0.36852 0.32833 0.25223 0.21957 0.0504 (9) 0.0496 (9) 0.0687* 0.0763* 0.0746* 0.0568* 0.0527* 0.0654* 0.0654* 0.0620* 0.0620* 0.0712* 0.0882* 0.0868* 0.0632* 0.0517* 0.0605* 0.0605* 0.0596* 0.0596* Atomic displacement parameters (Å2) I1A I1B O1 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 I2A I2B O2 C11 C12 C13 C14 C15 C16 C17 C18 U11 U22 U33 U12 U13 U23 0.0533 (13) 0.084 (2) 0.0456 (10) 0.0450 (12) 0.0773 (19) 0.102 (2) 0.083 (2) 0.0502 (14) 0.0370 (11) 0.0322 (11) 0.0442 (13) 0.0346 (12) 0.0379 (13) 0.0475 (8) 0.077 (3) 0.0550 (11) 0.0416 (12) 0.0745 (19) 0.105 (3) 0.086 (2) 0.0511 (15) 0.0355 (11) 0.0356 (11) 0.0445 (13) 0.0521 (9) 0.0428 (9) 0.0531 (11) 0.0273 (12) 0.0391 (15) 0.0490 (17) 0.0521 (18) 0.0387 (14) 0.0243 (11) 0.0297 (12) 0.0389 (14) 0.0499 (16) 0.0419 (15) 0.0585 (9) 0.0322 (19) 0.0514 (12) 0.0274 (12) 0.0488 (17) 0.071 (2) 0.064 (2) 0.0381 (14) 0.0259 (12) 0.0283 (12) 0.0427 (14) 0.0453 (9) 0.0599 (13) 0.0550 (12) 0.0504 (16) 0.0561 (19) 0.0402 (16) 0.0510 (19) 0.0530 (17) 0.0439 (14) 0.0448 (14) 0.0485 (15) 0.079 (2) 0.076 (2) 0.0512 (5) 0.0562 (13) 0.0709 (14) 0.0496 (16) 0.0551 (19) 0.0446 (18) 0.067 (2) 0.069 (2) 0.0484 (15) 0.0517 (15) 0.0420 (15) −0.0069 (5) −0.0067 (6) 0.0073 (8) −0.0049 (9) −0.0096 (13) −0.0163 (17) −0.0057 (15) 0.0023 (11) −0.0035 (9) −0.0045 (9) −0.0046 (10) −0.0019 (11) 0.0064 (10) 0.0129 (3) 0.0131 (8) −0.0111 (9) 0.0011 (9) −0.0020 (14) 0.006 (2) −0.0004 (18) −0.0081 (11) 0.0012 (9) 0.0032 (9) 0.0102 (10) 0.0019 (5) 0.0130 (10) 0.0063 (8) 0.0138 (11) 0.0319 (16) 0.0091 (16) −0.0130 (16) −0.0036 (12) 0.0054 (10) 0.0018 (10) −0.0082 (11) −0.0078 (12) 0.0160 (13) −0.0063 (3) 0.0055 (13) 0.0206 (10) 0.0093 (11) 0.0204 (15) 0.0004 (18) −0.0220 (19) −0.0073 (13) 0.0025 (10) 0.0071 (10) −0.0023 (11) 0.0139 (8) −0.0018 (11) −0.0161 (9) 0.0004 (11) −0.0049 (13) 0.0025 (14) 0.0118 (14) 0.0000 (12) −0.0011 (10) −0.0046 (10) −0.0064 (11) 0.0078 (15) 0.0039 (14) −0.0177 (5) −0.0043 (12) 0.0053 (10) −0.0039 (10) 0.0010 (14) −0.0078 (16) −0.0170 (17) −0.0075 (13) −0.0033 (10) 0.0012 (10) 0.0008 (11) Acta Cryst. (2009). E65, o3172 sup-5 supporting information C19 C20 0.0341 (12) 0.0347 (12) 0.0504 (16) 0.0433 (15) 0.0665 (19) 0.071 (2) 0.0033 (10) −0.0092 (10) −0.0068 (12) 0.0103 (12) −0.0087 (13) −0.0039 (13) Geometric parameters (Å, º) I1A—C8 I1B—C8 I2A—C18 I2B—C18 O1—C7 O2—C17 C1—C6 C1—C2 C1—C10 C2—C3 C3—C4 C4—C5 C5—C6 C6—C7 C7—C8 C8—C9 C9—C10 C2—H2 C3—H3 C4—H4 C5—H5 C8—H8 C9—H9A 2.170 (5) 2.211 (6) 2.180 (4) 2.192 (7) 1.220 (3) 1.223 (3) 1.404 (3) 1.398 (4) 1.506 (4) 1.369 (5) 1.377 (5) 1.381 (4) 1.400 (4) 1.490 (4) 1.510 (4) 1.518 (4) 1.514 (4) 0.9300 0.9300 0.9300 0.9300 0.9800 0.9700 C9—H9B C10—H10A C10—H10B C11—C12 C11—C16 C11—C20 C12—C13 C13—C14 C14—C15 C15—C16 C16—C17 C17—C18 C18—C19 C19—C20 C12—H12 C13—H13 C14—H14 C15—H15 C18—H18 C19—H19A C19—H19B C20—H20A C20—H20B 0.9700 0.9700 0.9700 1.389 (4) 1.402 (3) 1.503 (4) 1.384 (5) 1.370 (5) 1.367 (5) 1.405 (4) 1.482 (4) 1.511 (4) 1.513 (4) 1.510 (4) 0.9300 0.9300 0.9300 0.9300 0.9800 0.9700 0.9700 0.9700 0.9700 C2—C1—C6 C2—C1—C10 C6—C1—C10 C1—C2—C3 C2—C3—C4 C3—C4—C5 C4—C5—C6 C1—C6—C5 C1—C6—C7 C5—C6—C7 O1—C7—C6 O1—C7—C8 C6—C7—C8 I1A—C8—C7 I1A—C8—C9 I1B—C8—C7 I1B—C8—C9 C7—C8—C9 C8—C9—C10 118.2 (2) 121.1 (2) 120.7 (2) 121.8 (3) 120.0 (3) 119.9 (3) 120.8 (2) 119.3 (2) 121.5 (2) 119.21 (19) 122.0 (2) 120.6 (2) 117.38 (18) 105.13 (17) 112.4 (2) 106.32 (18) 109.5 (2) 113.1 (2) 112.3 (2) C12—C11—C16 C12—C11—C20 C16—C11—C20 C11—C12—C13 C12—C13—C14 C13—C14—C15 C14—C15—C16 C11—C16—C15 C11—C16—C17 C15—C16—C17 O2—C17—C16 O2—C17—C18 C16—C17—C18 I2A—C18—C17 I2A—C18—C19 I2B—C18—C17 I2B—C18—C19 C17—C18—C19 C18—C19—C20 118.3 (2) 121.1 (2) 120.6 (2) 121.3 (3) 120.3 (3) 119.8 (3) 121.0 (3) 119.3 (2) 121.8 (2) 118.9 (2) 122.1 (2) 120.7 (2) 117.2 (2) 104.62 (17) 112.60 (18) 105.0 (2) 109.1 (2) 112.7 (2) 112.9 (2) Acta Cryst. (2009). E65, o3172 sup-6 supporting information C1—C10—C9 C1—C2—H2 C3—C2—H2 C2—C3—H3 C4—C3—H3 C3—C4—H4 C5—C4—H4 C4—C5—H5 C6—C5—H5 I1A—C8—H8 I1B—C8—H8 C7—C8—H8 C9—C8—H8 C8—C9—H9A C8—C9—H9B C10—C9—H9A C10—C9—H9B H9A—C9—H9B C1—C10—H10A C1—C10—H10B C9—C10—H10A C9—C10—H10B H10A—C10—H10B 112.9 (2) 119.00 119.00 120.00 120.00 120.00 120.00 120.00 120.00 109.00 111.00 109.00 109.00 109.00 109.00 109.00 109.00 108.00 109.00 109.00 109.00 109.00 108.00 C11—C20—C19 C11—C12—H12 C13—C12—H12 C12—C13—H13 C14—C13—H13 C13—C14—H14 C15—C14—H14 C14—C15—H15 C16—C15—H15 I2A—C18—H18 I2B—C18—H18 C17—C18—H18 C19—C18—H18 C18—C19—H19A C18—C19—H19B C20—C19—H19A C20—C19—H19B H19A—C19—H19B C11—C20—H20A C11—C20—H20B C19—C20—H20A C19—C20—H20B H20A—C20—H20B 113.1 (2) 119.00 119.00 120.00 120.00 120.00 120.00 119.00 119.00 109.00 112.00 109.00 109.00 109.00 109.00 109.00 109.00 108.00 109.00 109.00 109.00 109.00 108.00 C6—C1—C2—C3 C10—C1—C2—C3 C2—C1—C6—C5 C2—C1—C6—C7 C10—C1—C6—C5 C10—C1—C6—C7 C2—C1—C10—C9 C6—C1—C10—C9 C1—C2—C3—C4 C2—C3—C4—C5 C3—C4—C5—C6 C4—C5—C6—C1 C4—C5—C6—C7 C1—C6—C7—O1 C1—C6—C7—C8 C5—C6—C7—O1 C5—C6—C7—C8 O1—C7—C8—I1A O1—C7—C8—C9 C6—C7—C8—I1A C6—C7—C8—C9 I1A—C8—C9—C10 C7—C8—C9—C10 C8—C9—C10—C1 −0.3 (4) 177.9 (3) −0.6 (3) −178.9 (2) −178.8 (2) 2.9 (3) 156.0 (2) −25.8 (3) 0.5 (5) 0.2 (5) −1.1 (4) 1.3 (4) 179.6 (2) 174.4 (2) −4.7 (3) −4.0 (3) 177.1 (2) 87.3 (2) −149.8 (2) −93.7 (2) 29.3 (3) 66.6 (3) −52.2 (3) 50.1 (3) C16—C11—C12—C13 C20—C11—C12—C13 C12—C11—C16—C15 C12—C11—C16—C17 C20—C11—C16—C15 C20—C11—C16—C17 C12—C11—C20—C19 C16—C11—C20—C19 C11—C12—C13—C14 C12—C13—C14—C15 C13—C14—C15—C16 C14—C15—C16—C11 C14—C15—C16—C17 C11—C16—C17—O2 C11—C16—C17—C18 C15—C16—C17—O2 C15—C16—C17—C18 O2—C17—C18—I2A O2—C17—C18—C19 C16—C17—C18—I2A C16—C17—C18—C19 I2A—C18—C19—C20 C17—C18—C19—C20 C18—C19—C20—C11 1.7 (4) −176.3 (3) −1.8 (3) 177.3 (2) 176.2 (2) −4.7 (3) −157.1 (2) 25.0 (3) −0.3 (5) −1.0 (5) 0.9 (5) 0.6 (4) −178.6 (3) −171.0 (2) 8.1 (3) 8.1 (3) −172.9 (2) −89.8 (2) 147.6 (2) 91.2 (2) −31.5 (3) −65.9 (3) 52.1 (3) −48.6 (3) Acta Cryst. (2009). E65, o3172 sup-7 supporting information Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···A C5—H5···Cg3 0.93 2.95 3.700 (4) 139 Acta Cryst. (2009). E65, o3172 sup-8