addenda and errata
O,O-Bis(2-tert-butyl-4-methoxyphenyl) chlorothiophosphonate. Corrigendum.
aDepartment of Chemistry, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and bDepartment of Physics, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
*Correspondence e-mail: orhanb@omu.edu.tr
In the original report by Odabaşoğlu, Büyükgüngör & Albayrak [Acta Cryst. (2005), E61, o2528–o2530], the structure was reported in the incorrect Cc. The structure is now reported as disordered in the correct C2/c. The P atom lies on a twofold rotation axis.A revised description of the hydrogen bonding is also given.
1. Comment
An ORTEP-3 (Farrugia, 1997) view of (I) and a packing diagram are shown in Figs. 1 and 2, respectively. The P atom lies on a twofold rotation axis, eading to disorder of the Cl and S atoms. Compound (I) has no classical hydrogen bonds, but there are two C—H⋯π interactions: H8A⋯Cg1= 3.12 (2) Å and C8—H8A⋯Cg1 = 122.8 (2)° (Cg1 is the centroid of the C1ii–C6ii ring), and H11A⋯Cg2 = 2.71 (2) Å and C11—H11A⋯Cg2 = 142.7 (1)° (Cg2 is the centroid of the C1iii–C6iii ring) [symmetry codes: (ii) x, 1 − y, + z; (iii) − x, − y, − z]. The dihedral angle between the symmetry-related benzene rings is 41.2 (2)°. Selected bond distances and angles are given in Table 1.
2. Experimental
2.1.1. Crystal data
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2.1.3. Refinement
|
All H atoms were refined freely. Atoms S1 and Cl1 were assigned to the same atomic site and refined freely with the same atomic coordinates and with fixed site-occupancy factors of 0.5.
Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536805027789/bt6713sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536805027789/bt6713Isup2.hkl
Compound (I) was prepared by the method of Odabaşoǧlu et al. (2005), using 2-tert-butyl-4-methoxyphenol and PSCl3 as starting materials. Crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution in n-hexane (yield 77%, m.p. 423 K). Analysis calculated: C 57.83, H 6.57%; found: C 57.36, H 6.38%.
All H atoms were refined freely. Atoms S1 and Cl1 were assigned to the same atomic site and refined freely with the same atomic coordinates and with fixed site-occupancy factors of 0.5.
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. A view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids·[Symmetry codes: (i) −x, y, −z + 1/2] | |
Fig. 2. A view of the packing of (I); C—H···π interactions are drawn as dashed lines. |
C22H30ClO4PS | F(000) = 968 |
Mr = 456.94 | Dx = 1.286 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 16485 reflections |
a = 23.592 (3) Å | θ = 1.7–26.7° |
b = 8.3111 (6) Å | µ = 0.34 mm−1 |
c = 12.5067 (14) Å | T = 150 K |
β = 105.740 (9)° | Prism, colorless |
V = 2360.3 (4) Å3 | 0.64 × 0.59 × 0.55 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 2146 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω scans | θmax = 26.0°, θmin = 1.8° |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | h = −28→28 |
Tmin = 0.824, Tmax = 0.869 | k = −10→10 |
16485 measured reflections | l = −15→15 |
2327 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.073 | All H-atom parameters refined |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0362P)2 + 1.6163P] where P = (Fo2 + 2Fc2)/3 |
2327 reflections | (Δ/σ)max = 0.002 |
192 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C22H30ClO4PS | V = 2360.3 (4) Å3 |
Mr = 456.94 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.592 (3) Å | µ = 0.34 mm−1 |
b = 8.3111 (6) Å | T = 150 K |
c = 12.5067 (14) Å | 0.64 × 0.59 × 0.55 mm |
β = 105.740 (9)° |
Stoe IPDS-II diffractometer | 2327 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2146 reflections with I > 2σ(I) |
Tmin = 0.824, Tmax = 0.869 | Rint = 0.032 |
16485 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.073 | All H-atom parameters refined |
S = 1.08 | Δρmax = 0.17 e Å−3 |
2327 reflections | Δρmin = −0.34 e Å−3 |
192 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.58872 (5) | 0.29212 (15) | 0.41994 (10) | 0.0224 (3) | |
C2 | 0.59796 (6) | 0.14466 (16) | 0.47516 (11) | 0.0258 (3) | |
C3 | 0.65010 (6) | 0.11722 (16) | 0.55649 (11) | 0.0272 (3) | |
C4 | 0.69210 (5) | 0.23993 (16) | 0.58337 (10) | 0.0249 (3) | |
C5 | 0.68201 (6) | 0.38769 (16) | 0.52737 (11) | 0.0252 (3) | |
C6 | 0.62988 (5) | 0.41888 (15) | 0.44326 (10) | 0.0233 (3) | |
C7 | 0.61903 (6) | 0.58369 (16) | 0.38318 (12) | 0.0296 (3) | |
C8 | 0.61032 (8) | 0.56105 (19) | 0.25687 (13) | 0.0374 (3) | |
C9 | 0.56458 (8) | 0.66639 (19) | 0.40646 (15) | 0.0402 (4) | |
C10 | 0.67218 (8) | 0.6983 (2) | 0.42394 (16) | 0.0453 (4) | |
C11 | 0.78481 (6) | 0.32952 (19) | 0.70159 (13) | 0.0343 (3) | |
O1 | 0.53449 (4) | 0.31975 (10) | 0.33826 (7) | 0.0257 (2) | |
O2 | 0.74184 (4) | 0.20383 (12) | 0.66690 (8) | 0.0319 (2) | |
P1 | 0.5000 | 0.19428 (5) | 0.2500 | 0.02610 (13) | |
Cl1 | 0.554354 (14) | 0.06331 (4) | 0.18992 (3) | 0.03162 (11) | 0.50 |
S1 | 0.554354 (14) | 0.06331 (4) | 0.18992 (3) | 0.03162 (11) | 0.50 |
H2 | 0.5683 (7) | 0.0634 (19) | 0.4571 (13) | 0.032 (4)* | |
H3 | 0.6579 (7) | 0.014 (2) | 0.5947 (13) | 0.034 (4)* | |
H5 | 0.7120 (7) | 0.4671 (19) | 0.5482 (13) | 0.029 (4)* | |
H8A | 0.6047 (8) | 0.668 (3) | 0.2193 (16) | 0.052 (5)* | |
H8B | 0.5774 (8) | 0.495 (2) | 0.2241 (15) | 0.043 (5)* | |
H8C | 0.6466 (9) | 0.512 (2) | 0.2429 (17) | 0.056 (5)* | |
H9A | 0.5571 (8) | 0.772 (2) | 0.3671 (15) | 0.051 (5)* | |
H9B | 0.5703 (8) | 0.686 (2) | 0.4892 (18) | 0.056 (5)* | |
H9C | 0.5281 (8) | 0.601 (2) | 0.3804 (15) | 0.047 (5)* | |
H10A | 0.7097 (9) | 0.650 (2) | 0.4105 (16) | 0.056 (6)* | |
H10B | 0.6816 (9) | 0.720 (2) | 0.5075 (19) | 0.059 (6)* | |
H10C | 0.6631 (9) | 0.798 (2) | 0.3852 (17) | 0.056 (5)* | |
H11A | 0.8030 (8) | 0.360 (2) | 0.6410 (15) | 0.042 (5)* | |
H11B | 0.8151 (8) | 0.282 (2) | 0.7644 (15) | 0.041 (4)* | |
H11C | 0.7671 (7) | 0.427 (2) | 0.7281 (14) | 0.035 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0207 (6) | 0.0240 (6) | 0.0204 (6) | 0.0000 (5) | 0.0020 (4) | −0.0009 (5) |
C2 | 0.0254 (6) | 0.0247 (6) | 0.0254 (6) | −0.0045 (5) | 0.0037 (5) | 0.0004 (5) |
C3 | 0.0293 (7) | 0.0261 (7) | 0.0243 (6) | −0.0001 (5) | 0.0037 (5) | 0.0030 (5) |
C4 | 0.0223 (6) | 0.0311 (7) | 0.0198 (6) | 0.0006 (5) | 0.0029 (5) | −0.0023 (5) |
C5 | 0.0241 (6) | 0.0262 (6) | 0.0246 (6) | −0.0044 (5) | 0.0053 (5) | −0.0041 (5) |
C6 | 0.0253 (6) | 0.0223 (6) | 0.0222 (6) | −0.0015 (5) | 0.0064 (5) | −0.0023 (5) |
C7 | 0.0315 (7) | 0.0212 (6) | 0.0333 (7) | −0.0037 (5) | 0.0041 (6) | 0.0019 (5) |
C8 | 0.0447 (9) | 0.0336 (8) | 0.0327 (8) | −0.0051 (7) | 0.0086 (7) | 0.0086 (6) |
C9 | 0.0443 (9) | 0.0242 (7) | 0.0498 (10) | 0.0051 (6) | 0.0087 (7) | −0.0019 (7) |
C10 | 0.0439 (9) | 0.0279 (8) | 0.0556 (11) | −0.0124 (7) | −0.0012 (8) | 0.0062 (7) |
C11 | 0.0253 (7) | 0.0395 (8) | 0.0322 (7) | −0.0019 (6) | −0.0021 (6) | −0.0082 (6) |
O1 | 0.0238 (4) | 0.0220 (4) | 0.0260 (5) | 0.0002 (3) | −0.0022 (4) | −0.0019 (4) |
O2 | 0.0252 (5) | 0.0360 (5) | 0.0283 (5) | −0.0015 (4) | −0.0033 (4) | 0.0005 (4) |
P1 | 0.0288 (2) | 0.0192 (2) | 0.0242 (2) | 0.000 | −0.00339 (18) | 0.000 |
Cl1 | 0.02605 (18) | 0.0368 (2) | 0.0320 (2) | 0.00652 (13) | 0.00781 (14) | −0.00242 (13) |
S1 | 0.02605 (18) | 0.0368 (2) | 0.0320 (2) | 0.00652 (13) | 0.00781 (14) | −0.00242 (13) |
C1—C2 | 1.3946 (18) | C8—H8C | 1.00 (2) |
C1—C6 | 1.4086 (17) | C9—H9A | 1.00 (2) |
C1—O1 | 1.4226 (14) | C9—H9B | 1.02 (2) |
C2—C3 | 1.3860 (18) | C9—H9C | 0.994 (19) |
C2—H2 | 0.955 (16) | C10—H10A | 1.03 (2) |
C3—C4 | 1.3979 (18) | C10—H10B | 1.02 (2) |
C3—H3 | 0.974 (17) | C10—H10C | 0.96 (2) |
C4—O2 | 1.3759 (15) | C11—O2 | 1.4383 (17) |
C4—C5 | 1.4017 (19) | C11—H11A | 0.998 (18) |
C5—C6 | 1.4088 (18) | C11—H11B | 0.990 (18) |
C5—H5 | 0.952 (16) | C11—H11C | 1.009 (17) |
C6—C7 | 1.5499 (18) | O1—P1 | 1.5750 (9) |
C7—C10 | 1.5468 (19) | P1—O1i | 1.5750 (9) |
C7—C8 | 1.548 (2) | P1—S1i | 1.9791 (4) |
C7—C9 | 1.552 (2) | P1—Cl1i | 1.9791 (4) |
C8—H8A | 1.00 (2) | P1—Cl1 | 1.9791 (4) |
C8—H8B | 0.948 (19) | ||
C2—C1—C6 | 123.25 (11) | C7—C9—H9A | 109.9 (11) |
C2—C1—O1 | 119.13 (11) | C7—C9—H9B | 111.8 (11) |
C6—C1—O1 | 117.58 (11) | H9A—C9—H9B | 108.6 (16) |
C3—C2—C1 | 119.77 (12) | C7—C9—H9C | 112.5 (11) |
C3—C2—H2 | 120.3 (9) | H9A—C9—H9C | 107.2 (15) |
C1—C2—H2 | 119.9 (9) | H9B—C9—H9C | 106.6 (15) |
C2—C3—C4 | 119.11 (12) | C7—C10—H10A | 111.4 (11) |
C2—C3—H3 | 121.1 (9) | C7—C10—H10B | 112.1 (11) |
C4—C3—H3 | 119.8 (9) | H10A—C10—H10B | 106.1 (16) |
O2—C4—C3 | 115.24 (12) | C7—C10—H10C | 108.5 (12) |
O2—C4—C5 | 124.38 (11) | H10A—C10—H10C | 109.9 (16) |
C3—C4—C5 | 120.39 (11) | H10B—C10—H10C | 108.8 (16) |
C4—C5—C6 | 121.99 (12) | O2—C11—H11A | 111.5 (10) |
C4—C5—H5 | 117.3 (9) | O2—C11—H11B | 104.1 (10) |
C6—C5—H5 | 120.7 (9) | H11A—C11—H11B | 109.7 (14) |
C1—C6—C5 | 115.48 (11) | O2—C11—H11C | 111.3 (9) |
C1—C6—C7 | 123.14 (11) | H11A—C11—H11C | 110.4 (14) |
C5—C6—C7 | 121.37 (11) | H11B—C11—H11C | 109.7 (13) |
C10—C7—C8 | 106.40 (13) | C1—O1—P1 | 126.11 (8) |
C10—C7—C6 | 111.83 (11) | C4—O2—C11 | 117.18 (11) |
C8—C7—C6 | 110.24 (11) | O1—P1—O1i | 97.08 (7) |
C10—C7—C9 | 107.68 (13) | O1—P1—S1i | 111.27 (4) |
C8—C7—C9 | 110.96 (12) | O1i—P1—S1i | 111.44 (3) |
C6—C7—C9 | 109.67 (12) | O1—P1—Cl1i | 111.27 (4) |
C7—C8—H8A | 109.7 (11) | O1i—P1—Cl1i | 111.44 (3) |
C7—C8—H8B | 112.2 (11) | S1i—P1—Cl1i | 0.00 (2) |
H8A—C8—H8B | 108.9 (16) | O1—P1—Cl1 | 111.44 (3) |
C7—C8—H8C | 110.0 (12) | O1i—P1—Cl1 | 111.27 (4) |
H8A—C8—H8C | 106.8 (16) | S1i—P1—Cl1 | 113.26 (3) |
H8B—C8—H8C | 109.0 (16) | Cl1i—P1—Cl1 | 113.26 (3) |
C6—C1—C2—C3 | −0.8 (2) | C5—C6—C7—C10 | 2.35 (18) |
O1—C1—C2—C3 | −178.73 (11) | C1—C6—C7—C8 | −60.70 (16) |
C1—C2—C3—C4 | 1.4 (2) | C5—C6—C7—C8 | 120.51 (13) |
C2—C3—C4—O2 | 178.39 (11) | C1—C6—C7—C9 | 61.76 (16) |
C2—C3—C4—C5 | −1.14 (19) | C5—C6—C7—C9 | −117.03 (14) |
O2—C4—C5—C6 | −179.21 (11) | C2—C1—O1—P1 | −40.07 (15) |
C3—C4—C5—C6 | 0.28 (19) | C6—C1—O1—P1 | 141.89 (10) |
C2—C1—C6—C5 | −0.05 (18) | C3—C4—O2—C11 | −176.65 (12) |
O1—C1—C6—C5 | 177.90 (10) | C5—C4—O2—C11 | 2.86 (18) |
C2—C1—C6—C7 | −178.90 (12) | C1—O1—P1—O1i | −155.66 (11) |
O1—C1—C6—C7 | −0.95 (18) | C1—O1—P1—S1i | 88.01 (9) |
C4—C5—C6—C1 | 0.31 (18) | C1—O1—P1—Cl1i | 88.01 (9) |
C4—C5—C6—C7 | 179.19 (12) | C1—O1—P1—Cl1 | −39.46 (10) |
C1—C6—C7—C10 | −178.86 (13) |
Symmetry code: (i) −x+1, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C22H30ClO4PS |
Mr | 456.94 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 150 |
a, b, c (Å) | 23.592 (3), 8.3111 (6), 12.5067 (14) |
β (°) | 105.740 (9) |
V (Å3) | 2360.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.64 × 0.59 × 0.55 |
Data collection | |
Diffractometer | Stoe IPDS-II diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.824, 0.869 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16485, 2327, 2146 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.073, 1.08 |
No. of reflections | 2327 |
No. of parameters | 192 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.17, −0.34 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-AREA, X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
C1—C2 | 1.3946 (18) | C4—C5 | 1.4017 (19) |
C1—C6 | 1.4086 (17) | C5—C6 | 1.4088 (18) |
C1—O1 | 1.4226 (14) | O1—P1 | 1.5750 (9) |
C2—C3 | 1.3860 (18) | P1—S1i | 1.9791 (4) |
C3—C4 | 1.3979 (18) | P1—Cl1 | 1.9791 (4) |
C2—C1—C6 | 123.25 (11) | C4—C5—C6 | 121.99 (12) |
C2—C1—O1 | 119.13 (11) | C1—C6—C5 | 115.48 (11) |
C6—C1—O1 | 117.58 (11) | O1—P1—O1i | 97.08 (7) |
C3—C2—C1 | 119.77 (12) | O1—P1—S1i | 111.27 (4) |
C2—C3—C4 | 119.11 (12) | O1—P1—Cl1 | 111.44 (3) |
C3—C4—C5 | 120.39 (11) | S1i—P1—Cl1 | 113.26 (3) |
Symmetry code: (i) −x+1, y, −z+1/2. |
References
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED32 (Version 1.04). Stoe & Cie, Darmstadt, Germany. Google Scholar
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An ORTEP-3 (Farrugia, 1997) view of (I) and a packing diagram are shown in Figs. 1 and 2, respectively. Compound (I) has no classical hydrogen bonds but there are two C—H···π interactions: H8A···Cg1= 3.12 (2) Å and C8—H8A···Cg1 = 122.8 (2)° [Cg1 is the centroid of the C1i–C6i ring; and H11A···Cg2 = 2.71 (2) Å and C11—H11A···Cg2 = 142.7 (1)° (Cg2 is the centroid of the C1ii–C6ii ring); symmetry codes: (i) x, 1 − y, 1/2 + z; (ii) 1/2 − x, 1/2 − y, − z]. The dihedral angle between the symmetry-related benzene rings in (I) is 41.2 (2)°. Selected bond distances and angles for (I) are given in Table 1. The benzene ring is planar, with a maximum deviation from the plane defined by the six ring atoms of 0.007 (1) Å (for C3).