Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102013112/av1114sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102013112/av1114Isup2.hkl |
CCDC reference: 195615
A solution of phenanthrenequinone (0.05 M) in the presence of an excess of 2-methyl-4-phenylthiazole in benzene solution was irradiated with light of wavelength longer than 400 nm. After completion of the reaction, the solvent was removed in vacuo and the residue was separated by column chromatography on silica gel to afford the title compound. Single crystals suitable for X-ray diffraction analysis were obtained from slow evaporation of an acetone–petroleum ether solution.
The H atoms were fixed geometrically and treated as riding atoms on their parent C atoms, with C—H distances in the range 0.93–0.97 Å and Uiso(H) = 1.2Ueq(C). Since the Flack (1983) parameter was unable to determine the absolute structure, the 2268 Friedel equivalents were merged before the final refinements. The absolute structure was then arbitrarily chosen.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
C24H17NO2S | F(000) = 800 |
Mr = 383.45 | Dx = 1.351 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 7025 reflections |
a = 10.7999 (1) Å | θ = 2.5–28.3° |
b = 9.2851 (1) Å | µ = 0.19 mm−1 |
c = 18.7949 (3) Å | T = 213 K |
V = 1884.72 (4) Å3 | Block, yellow |
Z = 4 | 0.50 × 0.32 × 0.22 mm |
Siemens SMART CCD area-detector diffractometer | 2375 independent reflections |
Radiation source: fine-focus sealed tube | 1924 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.098 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 2.5° |
ω scans | h = −14→13 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −10→12 |
Tmin = 0.910, Tmax = 0.959 | l = −22→24 |
10677 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.074P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
2375 reflections | Δρmax = 0.29 e Å−3 |
255 parameters | Δρmin = −0.41 e Å−3 |
1 restraint | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.011 (2) |
C24H17NO2S | V = 1884.72 (4) Å3 |
Mr = 383.45 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 10.7999 (1) Å | µ = 0.19 mm−1 |
b = 9.2851 (1) Å | T = 213 K |
c = 18.7949 (3) Å | 0.50 × 0.32 × 0.22 mm |
Siemens SMART CCD area-detector diffractometer | 2375 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 1924 reflections with I > 2σ(I) |
Tmin = 0.910, Tmax = 0.959 | Rint = 0.098 |
10677 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 1 restraint |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.29 e Å−3 |
2375 reflections | Δρmin = −0.41 e Å−3 |
255 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 | ||
S1 | 0.37224 (9) | 0.59958 (10) | 0.00909 (5) | 0.0343 (3) | |
O1 | 0.4913 (2) | 0.8164 (2) | 0.17363 (13) | 0.0248 (5) | |
O2 | 0.3769 (2) | 0.5527 (3) | 0.14726 (14) | 0.0318 (6) | |
N1 | 0.5567 (2) | 0.7521 (3) | 0.05771 (16) | 0.0251 (6) | |
C1 | 0.5283 (3) | 0.6917 (4) | 0.20767 (17) | 0.0220 (7) | |
C2 | 0.6277 (3) | 0.7046 (4) | 0.25853 (17) | 0.0229 (7) | |
C3 | 0.6890 (3) | 0.8373 (4) | 0.26976 (18) | 0.0279 (7) | |
H3 | 0.6668 | 0.9176 | 0.2431 | 0.033* | |
C4 | 0.7790 (4) | 0.8478 (5) | 0.3187 (2) | 0.0352 (9) | |
H4 | 0.8160 | 0.9364 | 0.3276 | 0.042* | |
C5 | 0.8170 (4) | 0.7265 (5) | 0.3561 (2) | 0.0415 (10) | |
H5 | 0.8803 | 0.7350 | 0.3894 | 0.050* | |
C6 | 0.7637 (4) | 0.5959 (4) | 0.3451 (2) | 0.0339 (8) | |
H6 | 0.7918 | 0.5161 | 0.3703 | 0.041* | |
C7 | 0.6668 (3) | 0.5803 (4) | 0.29613 (18) | 0.0271 (7) | |
C8 | 0.6022 (4) | 0.4443 (4) | 0.28271 (18) | 0.0292 (8) | |
C9 | 0.6367 (4) | 0.3156 (4) | 0.3191 (2) | 0.0395 (10) | |
H9 | 0.7026 | 0.3158 | 0.3510 | 0.047* | |
C10 | 0.5694 (5) | 0.1884 (4) | 0.3062 (2) | 0.0431 (11) | |
H10 | 0.5868 | 0.1064 | 0.3328 | 0.052* | |
C11 | 0.4802 (4) | 0.1827 (4) | 0.2559 (2) | 0.0414 (10) | |
H11 | 0.4401 | 0.0961 | 0.2466 | 0.050* | |
C12 | 0.4486 (4) | 0.3048 (4) | 0.2186 (2) | 0.0347 (9) | |
H12 | 0.3870 | 0.2998 | 0.1840 | 0.042* | |
C13 | 0.5075 (3) | 0.4359 (4) | 0.23166 (17) | 0.0251 (7) | |
C14 | 0.4737 (3) | 0.5649 (4) | 0.19417 (18) | 0.0236 (7) | |
C15 | 0.3544 (3) | 0.6689 (4) | 0.09831 (18) | 0.0243 (7) | |
H15 | 0.2710 | 0.7080 | 0.1051 | 0.029* | |
C16 | 0.4528 (3) | 0.7915 (4) | 0.10186 (18) | 0.0229 (7) | |
C17 | 0.5272 (3) | 0.6637 (4) | 0.0092 (2) | 0.0284 (7) | |
C18 | 0.3964 (3) | 0.9342 (4) | 0.07739 (18) | 0.0245 (7) | |
C19 | 0.2938 (3) | 0.9918 (4) | 0.1142 (2) | 0.0284 (7) | |
H19 | 0.2604 | 0.9418 | 0.1525 | 0.034* | |
C20 | 0.2429 (4) | 1.1205 (4) | 0.0939 (2) | 0.0317 (8) | |
H20 | 0.1774 | 1.1583 | 0.1200 | 0.038* | |
C21 | 0.2860 (4) | 1.1947 (4) | 0.0363 (2) | 0.0383 (9) | |
H21 | 0.2485 | 1.2801 | 0.0220 | 0.046* | |
C22 | 0.3878 (5) | 1.1394 (5) | −0.0009 (3) | 0.0510 (12) | |
H22 | 0.4199 | 1.1907 | −0.0392 | 0.061* | |
C23 | 0.4418 (4) | 1.0094 (4) | 0.0184 (2) | 0.0387 (9) | |
H23 | 0.5078 | 0.9726 | −0.0077 | 0.046* | |
C24 | 0.6128 (4) | 0.6123 (5) | −0.0483 (2) | 0.0426 (10) | |
H24A | 0.6145 | 0.5090 | −0.0485 | 0.064* | |
H24B | 0.6947 | 0.6485 | −0.0395 | 0.064* | |
H24C | 0.5840 | 0.6466 | −0.0935 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0403 (5) | 0.0370 (5) | 0.0257 (4) | −0.0108 (4) | −0.0081 (4) | −0.0035 (4) |
O1 | 0.0260 (12) | 0.0252 (12) | 0.0230 (11) | 0.0004 (9) | −0.0058 (10) | −0.0015 (10) |
O2 | 0.0382 (15) | 0.0264 (13) | 0.0307 (13) | −0.0098 (11) | −0.0134 (11) | 0.0079 (11) |
N1 | 0.0168 (12) | 0.0337 (16) | 0.0249 (14) | 0.0026 (12) | −0.0023 (11) | −0.0018 (12) |
C1 | 0.0217 (16) | 0.0246 (17) | 0.0198 (16) | 0.0021 (13) | −0.0018 (12) | −0.0001 (13) |
C2 | 0.0236 (16) | 0.0287 (17) | 0.0163 (15) | 0.0020 (13) | 0.0010 (13) | −0.0042 (13) |
C3 | 0.0280 (18) | 0.0366 (18) | 0.0191 (16) | −0.0023 (15) | 0.0009 (13) | −0.0065 (14) |
C4 | 0.0270 (18) | 0.050 (2) | 0.0282 (18) | −0.0100 (17) | −0.0049 (15) | −0.0067 (17) |
C5 | 0.037 (2) | 0.062 (3) | 0.0250 (19) | 0.002 (2) | −0.0090 (17) | −0.0078 (19) |
C6 | 0.0242 (18) | 0.053 (2) | 0.0247 (17) | 0.0064 (16) | −0.0036 (14) | −0.0005 (18) |
C7 | 0.0325 (19) | 0.0349 (18) | 0.0139 (14) | 0.0069 (14) | 0.0018 (13) | −0.0026 (14) |
C8 | 0.038 (2) | 0.0299 (18) | 0.0198 (16) | 0.0104 (15) | 0.0007 (14) | −0.0008 (14) |
C9 | 0.065 (3) | 0.032 (2) | 0.0216 (18) | 0.0196 (19) | −0.0002 (18) | 0.0001 (15) |
C10 | 0.067 (3) | 0.029 (2) | 0.034 (2) | 0.0146 (19) | 0.008 (2) | 0.0032 (17) |
C11 | 0.056 (3) | 0.026 (2) | 0.042 (2) | −0.0007 (17) | 0.005 (2) | 0.0028 (17) |
C12 | 0.042 (2) | 0.029 (2) | 0.0322 (19) | −0.0009 (16) | −0.0010 (17) | 0.0005 (15) |
C13 | 0.0268 (18) | 0.0288 (18) | 0.0199 (16) | 0.0028 (13) | 0.0018 (13) | −0.0001 (13) |
C14 | 0.0190 (15) | 0.0297 (17) | 0.0220 (16) | 0.0002 (13) | −0.0010 (12) | 0.0007 (13) |
C15 | 0.0285 (17) | 0.0218 (16) | 0.0226 (17) | −0.0013 (13) | −0.0043 (13) | 0.0028 (14) |
C16 | 0.0193 (15) | 0.0276 (17) | 0.0216 (16) | −0.0040 (12) | −0.0024 (13) | 0.0006 (13) |
C17 | 0.0259 (17) | 0.0327 (17) | 0.0265 (16) | 0.0064 (13) | −0.0017 (15) | 0.0006 (16) |
C18 | 0.0250 (16) | 0.0267 (18) | 0.0218 (16) | −0.0057 (14) | −0.0059 (13) | 0.0024 (13) |
C19 | 0.0264 (18) | 0.0298 (18) | 0.0289 (17) | −0.0022 (14) | 0.0025 (14) | 0.0039 (15) |
C20 | 0.0260 (18) | 0.0305 (19) | 0.038 (2) | 0.0038 (14) | 0.0016 (15) | −0.0009 (16) |
C21 | 0.033 (2) | 0.032 (2) | 0.050 (2) | −0.0010 (16) | −0.0040 (18) | 0.0111 (17) |
C22 | 0.057 (3) | 0.044 (2) | 0.052 (3) | −0.001 (2) | 0.007 (2) | 0.025 (2) |
C23 | 0.032 (2) | 0.041 (2) | 0.043 (2) | 0.0022 (15) | 0.0158 (18) | 0.0143 (19) |
C24 | 0.049 (3) | 0.051 (3) | 0.027 (2) | 0.0151 (19) | 0.0012 (18) | −0.0023 (18) |
S1—C17 | 1.776 (3) | C10—C11 | 1.350 (6) |
S1—C15 | 1.806 (4) | C10—H10 | 0.9300 |
O1—C1 | 1.382 (4) | C11—C12 | 1.377 (6) |
O1—C16 | 1.430 (4) | C11—H11 | 0.9300 |
O2—C14 | 1.373 (4) | C12—C13 | 1.395 (5) |
O2—C15 | 1.438 (4) | C12—H12 | 0.9300 |
N1—C17 | 1.268 (5) | C13—C14 | 1.437 (5) |
N1—C16 | 1.443 (4) | C15—C16 | 1.559 (5) |
C1—C14 | 1.341 (5) | C15—H15 | 0.9800 |
C1—C2 | 1.442 (4) | C16—C18 | 1.529 (5) |
C2—C3 | 1.414 (5) | C17—C24 | 1.500 (6) |
C2—C7 | 1.417 (5) | C18—C23 | 1.399 (5) |
C3—C4 | 1.342 (5) | C18—C19 | 1.411 (5) |
C3—H3 | 0.9300 | C19—C20 | 1.370 (5) |
C4—C5 | 1.390 (6) | C19—H19 | 0.9300 |
C4—H4 | 0.9300 | C20—C21 | 1.365 (6) |
C5—C6 | 1.358 (6) | C20—H20 | 0.9300 |
C5—H5 | 0.9300 | C21—C22 | 1.401 (6) |
C6—C7 | 1.402 (5) | C21—H21 | 0.9300 |
C6—H6 | 0.9300 | C22—C23 | 1.389 (6) |
C7—C8 | 1.465 (5) | C22—H22 | 0.9300 |
C8—C13 | 1.404 (5) | C23—H23 | 0.9300 |
C8—C9 | 1.427 (5) | C24—H24A | 0.9600 |
C9—C10 | 1.408 (7) | C24—H24B | 0.9600 |
C9—H9 | 0.9300 | C24—H24C | 0.9600 |
C17—S1—C15 | 88.85 (17) | C1—C14—O2 | 122.0 (3) |
C1—O1—C16 | 112.7 (3) | C1—C14—C13 | 121.9 (3) |
C14—O2—C15 | 118.5 (3) | O2—C14—C13 | 116.1 (3) |
C17—N1—C16 | 112.4 (3) | O2—C15—C16 | 113.9 (3) |
C14—C1—O1 | 121.4 (3) | O2—C15—S1 | 108.0 (2) |
C14—C1—C2 | 121.7 (3) | C16—C15—S1 | 103.1 (2) |
O1—C1—C2 | 116.9 (3) | O2—C15—H15 | 110.5 |
C3—C2—C7 | 119.7 (3) | C16—C15—H15 | 110.5 |
C3—C2—C1 | 121.3 (3) | S1—C15—H15 | 110.5 |
C7—C2—C1 | 119.0 (3) | O1—C16—N1 | 110.9 (3) |
C4—C3—C2 | 120.3 (4) | O1—C16—C18 | 105.1 (3) |
C4—C3—H3 | 119.8 | N1—C16—C18 | 110.9 (3) |
C2—C3—H3 | 119.8 | O1—C16—C15 | 110.9 (3) |
C3—C4—C5 | 120.1 (4) | N1—C16—C15 | 108.7 (3) |
C3—C4—H4 | 119.9 | C18—C16—C15 | 110.4 (3) |
C5—C4—H4 | 119.9 | N1—C17—C24 | 124.6 (3) |
C6—C5—C4 | 121.4 (4) | N1—C17—S1 | 117.1 (3) |
C6—C5—H5 | 119.3 | C24—C17—S1 | 118.3 (3) |
C4—C5—H5 | 119.3 | C23—C18—C19 | 118.3 (3) |
C5—C6—C7 | 120.6 (4) | C23—C18—C16 | 122.1 (3) |
C5—C6—H6 | 119.7 | C19—C18—C16 | 119.6 (3) |
C7—C6—H6 | 119.7 | C20—C19—C18 | 120.6 (3) |
C6—C7—C2 | 117.8 (3) | C20—C19—H19 | 119.7 |
C6—C7—C8 | 123.9 (3) | C18—C19—H19 | 119.7 |
C2—C7—C8 | 118.3 (3) | C21—C20—C19 | 121.6 (4) |
C13—C8—C9 | 118.1 (4) | C21—C20—H20 | 119.2 |
C13—C8—C7 | 120.8 (3) | C19—C20—H20 | 119.2 |
C9—C8—C7 | 121.0 (3) | C20—C21—C22 | 118.6 (4) |
C10—C9—C8 | 119.0 (4) | C20—C21—H21 | 120.7 |
C10—C9—H9 | 120.5 | C22—C21—H21 | 120.7 |
C8—C9—H9 | 120.5 | C23—C22—C21 | 121.2 (4) |
C11—C10—C9 | 121.5 (4) | C23—C22—H22 | 119.4 |
C11—C10—H10 | 119.3 | C21—C22—H22 | 119.4 |
C9—C10—H10 | 119.3 | C22—C23—C18 | 119.6 (4) |
C10—C11—C12 | 120.1 (4) | C22—C23—H23 | 120.2 |
C10—C11—H11 | 119.9 | C18—C23—H23 | 120.2 |
C12—C11—H11 | 119.9 | C17—C24—H24A | 109.5 |
C11—C12—C13 | 121.0 (4) | C17—C24—H24B | 109.5 |
C11—C12—H12 | 119.5 | H24A—C24—H24B | 109.5 |
C13—C12—H12 | 119.5 | C17—C24—H24C | 109.5 |
C12—C13—C8 | 120.1 (3) | H24A—C24—H24C | 109.5 |
C12—C13—C14 | 121.7 (3) | H24B—C24—H24C | 109.5 |
C8—C13—C14 | 118.3 (3) | ||
C16—O1—C1—C14 | −34.6 (4) | C12—C13—C14—C1 | 178.6 (4) |
C16—O1—C1—C2 | 145.8 (3) | C8—C13—C14—C1 | −1.3 (5) |
C14—C1—C2—C3 | 176.7 (3) | C12—C13—C14—O2 | 2.8 (5) |
O1—C1—C2—C3 | −3.7 (5) | C8—C13—C14—O2 | −177.1 (3) |
C14—C1—C2—C7 | −1.2 (5) | C14—O2—C15—C16 | 4.5 (4) |
O1—C1—C2—C7 | 178.4 (3) | C14—O2—C15—S1 | 118.4 (3) |
C7—C2—C3—C4 | −3.9 (5) | C17—S1—C15—O2 | −95.9 (2) |
C1—C2—C3—C4 | 178.2 (3) | C17—S1—C15—C16 | 25.0 (2) |
C2—C3—C4—C5 | 3.4 (5) | C1—O1—C16—N1 | −69.0 (3) |
C3—C4—C5—C6 | −0.9 (6) | C1—O1—C16—C18 | 171.1 (3) |
C4—C5—C6—C7 | −1.0 (6) | C1—O1—C16—C15 | 51.9 (3) |
C5—C6—C7—C2 | 0.5 (5) | C17—N1—C16—O1 | 146.4 (3) |
C5—C6—C7—C8 | −178.2 (4) | C17—N1—C16—C18 | −97.2 (3) |
C3—C2—C7—C6 | 1.9 (5) | C17—N1—C16—C15 | 24.3 (4) |
C1—C2—C7—C6 | 179.8 (3) | O2—C15—C16—O1 | −37.7 (4) |
C3—C2—C7—C8 | −179.3 (3) | S1—C15—C16—O1 | −154.5 (2) |
C1—C2—C7—C8 | −1.4 (5) | O2—C15—C16—N1 | 84.5 (3) |
C6—C7—C8—C13 | −178.6 (3) | S1—C15—C16—N1 | −32.3 (3) |
C2—C7—C8—C13 | 2.7 (5) | O2—C15—C16—C18 | −153.7 (3) |
C6—C7—C8—C9 | −0.9 (5) | S1—C15—C16—C18 | 89.5 (3) |
C2—C7—C8—C9 | −179.7 (3) | C16—N1—C17—C24 | 174.9 (3) |
C13—C8—C9—C10 | −4.3 (6) | C16—N1—C17—S1 | −3.9 (4) |
C7—C8—C9—C10 | 178.0 (4) | C15—S1—C17—N1 | −14.4 (3) |
C8—C9—C10—C11 | 5.6 (6) | C15—S1—C17—C24 | 166.7 (3) |
C9—C10—C11—C12 | −3.4 (6) | O1—C16—C18—C23 | 121.4 (4) |
C10—C11—C12—C13 | 0.0 (6) | N1—C16—C18—C23 | 1.5 (5) |
C11—C12—C13—C8 | 1.2 (6) | C15—C16—C18—C23 | −119.0 (4) |
C11—C12—C13—C14 | −178.7 (4) | O1—C16—C18—C19 | −59.7 (4) |
C9—C8—C13—C12 | 1.0 (5) | N1—C16—C18—C19 | −179.6 (3) |
C7—C8—C13—C12 | 178.7 (3) | C15—C16—C18—C19 | 59.9 (4) |
C9—C8—C13—C14 | −179.1 (3) | C23—C18—C19—C20 | −2.1 (5) |
C7—C8—C13—C14 | −1.4 (5) | C16—C18—C19—C20 | 179.0 (3) |
O1—C1—C14—O2 | −1.4 (5) | C18—C19—C20—C21 | 2.5 (6) |
C2—C1—C14—O2 | 178.2 (3) | C19—C20—C21—C22 | −2.5 (6) |
O1—C1—C14—C13 | −177.0 (3) | C20—C21—C22—C23 | 2.3 (7) |
C2—C1—C14—C13 | 2.6 (5) | C21—C22—C23—C18 | −2.0 (7) |
C15—O2—C14—C1 | 16.2 (5) | C19—C18—C23—C22 | 1.9 (6) |
C15—O2—C14—C13 | −168.0 (3) | C16—C18—C23—C22 | −179.2 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N1i | 0.98 | 2.51 | 3.385 (4) | 149 |
Symmetry code: (i) x−1/2, −y+3/2, z. |
Experimental details
Crystal data | |
Chemical formula | C24H17NO2S |
Mr | 383.45 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 213 |
a, b, c (Å) | 10.7999 (1), 9.2851 (1), 18.7949 (3) |
V (Å3) | 1884.72 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.50 × 0.32 × 0.22 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.910, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10677, 2375, 1924 |
Rint | 0.098 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.130, 1.00 |
No. of reflections | 2375 |
No. of parameters | 255 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.41 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
S1—C17 | 1.776 (3) | O2—C14 | 1.373 (4) |
S1—C15 | 1.806 (4) | O2—C15 | 1.438 (4) |
O1—C1 | 1.382 (4) | N1—C17 | 1.268 (5) |
O1—C16 | 1.430 (4) | N1—C16 | 1.443 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N1i | 0.98 | 2.51 | 3.385 (4) | 149 |
Symmetry code: (i) x−1/2, −y+3/2, z. |
Photoinduced cycloaddition reactions of excited state carbonyl compounds with oxazole and thiazole derivatives have not been widely investigated (Secretar et al., 1983; Griesbeck et al., 2000). We have investigated photoreactions of phenanthrenequinone with 2-methyl-4-phenylthiazole, and isolated the title compound as the product. An X-ray crystal structure analysis has been undertaken to elucidate its steric configuration, and the results are presented here.
The bond lengths and angles in (I) (Fig. 1) are within normal ranges (Allen et al., 1987). Those within the phenanthrene moiety (C1–C14) and the dioxine ring (C1/C14/O2/C15/C16/O1) agree with the corresponding values in a related structure (Usman et al., 2002), while those within the thiazoline ring (C15–C17/S1/N1) are comparable with those in a reported thiazole derivative (Exstrand & van der Helm, 1977).
The thiazoline ring adopts an envelope conformation, with atom C15 displaced by 0.527 (3) Å from the N1/C16/S1/C17 plane. Methyl atom C24, attached to atom C17, deviates by 0.206 (4) Å from the thiazoline mean plane, while the phenyl ring (C18–C23) attached at C16 is nearly orthogonal with respect to the thiazoline plane, corresponding to a dihedral angle of 86.9 (2)° between their planes. The C15—C16—C18 and S1—C15—C16 bond angles and the O2—C15—C16—O1 torsion angle are 103.1 (2), 110.4 (3) and -37.7 (4)°, respectively, indicating a staggered configuration of the sp3 states of atoms C15 and C16 joining the thiazoline, dioxine and phenyl rings. These two atoms also govern the angle between the thiazoline and dioxine rings [76.9 (2)°].
The dioxine ring is distorted from planarity towards a half-chair conformation, with atoms O1 and C16 displaced by -0.268 (2) and 0.381 (3) Å, respectively, from the C1/C14/O2/C15 plane. A local pseudo-twofold axis passes through the midpoints of the O1—C16 and O2—C14 bonds.
The planar phenanthrene moiety has a maximum deviation of 0.044 (5) Å at atom C10. The dihedral angles between the benzene rings in the phenanthrene moiety are within 1.3 (2)°, while that between the phenanthrene and dioxine rings is 11.0 (1)°.
In Fig. 1, atoms C15 and C16 are the R chiral centers. The photoinduced cycloaddition reaction of both achiral phenanthrenequinone and 2-methyl-4-phenylthiazole gives chiral C atoms at the additional ring of the title compound.
The molecules are packed into chains along the a direction (Fig. 2) by a weak C15—H15···N1i interaction (see Table 2 for symmetry code). The packing is stabilized by this interaction, together with dipole—dipole and van der Waals interactions.