Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032850/kp2119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032850/kp2119Isup2.hkl |
CCDC reference: 657716
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.047
- wR factor = 0.125
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.826 0.988 Tmin(prime) and Tmax expected: 0.970 0.988 RR(prime) = 0.851 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.85 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.56 Ratio
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C9 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound, (I), was synthesized by photo-induced reaction between 4-methoxybenzaldehyde (0.05 M) and an excess amount of 1-phenyl-2-trimethyl-silylacetylene (0.15 M) in a benzene solution. The title compound was isolated using silica gel column chromatography. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the solvents from a petroleum ether-acetone solution (V:V=2:1).
All H atoms were refined using a riding model, with C—H distances in the range 0.93–0.96 Å. The Uiso(H) values were constrained to be 1.5Ueq of the carrier atom for methyl H and 1.2Ueq for the remaining H atoms.
The photochemistry of alkynes is of permanent research interest (Wang et al., 2005). As part of our recent work on photoinduced reactions of aldehydes with alkynes, the title compound was obtained by the reaction of photoexcited 4-methoxybenzaldehyde with trimethylsilyphenylethyne. X-ray structure analysis of the title compound was carried out to elucidate its structure.
Since the atom C9 is chiral and the space group is centrosymmetric, the crystal is a racemate. Bond lengths and angles of the title compound are within normal ranges (Allen et al., 1987). The indane ring is essentially planar with a maximum deviation of 0.053 (2)Å for atom C9. The benzene ring was twisted from the indane ring with the dihedral angle of 81.53 (8)°. The methoxy group attached at the atom C9 is almost coplanar with the indane ring with C16—O1—C3—C4 torsion angle of -179.31 (14)°.
The molecules are linked into chains approximately down the b axis and stabilized by three intermolecular C—H···O interactions (Table 1). These interactions form R23(8) hydrogen bond ring motifs (Bernstein et al., 1995).
For bond length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For general background and related literature, see: Wang et al. (2005).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C16H14O2 | F(000) = 504 |
Mr = 238.27 | Dx = 1.273 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2136 reflections |
a = 8.3603 (4) Å | θ = 2.5–26.5° |
b = 6.4935 (3) Å | µ = 0.08 mm−1 |
c = 23.1904 (11) Å | T = 100 K |
β = 99.106 (2)° | Block, colourless |
V = 1243.09 (10) Å3 | 0.36 × 0.19 × 0.14 mm |
Z = 4 |
Bruker SMART APEX II CCD area-detector diffractometer | 2548 independent reflections |
Radiation source: fine-focus sealed tube | 1867 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.5°, θmin = 1.8° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −7→8 |
Tmin = 0.826, Tmax = 0.989 | l = −24→29 |
10552 measured 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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.283P] where P = (Fo2 + 2Fc2)/3 |
2548 reflections | (Δ/σ)max = 0.001 |
164 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C16H14O2 | V = 1243.09 (10) Å3 |
Mr = 238.27 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3603 (4) Å | µ = 0.08 mm−1 |
b = 6.4935 (3) Å | T = 100 K |
c = 23.1904 (11) Å | 0.36 × 0.19 × 0.14 mm |
β = 99.106 (2)° |
Bruker SMART APEX II CCD area-detector diffractometer | 2548 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1867 reflections with I > 2σ(I) |
Tmin = 0.826, Tmax = 0.989 | Rint = 0.047 |
10552 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.20 e Å−3 |
2548 reflections | Δρmin = −0.25 e Å−3 |
164 parameters |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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 | ||
O1 | 0.38826 (13) | 0.31089 (17) | 0.44441 (5) | 0.0249 (3) | |
O2 | −0.23284 (14) | 0.90321 (17) | 0.44183 (5) | 0.0278 (3) | |
C1 | −0.04029 (19) | 0.4488 (2) | 0.40722 (7) | 0.0190 (4) | |
C2 | 0.09832 (19) | 0.3295 (2) | 0.41001 (7) | 0.0200 (4) | |
H2A | 0.0945 | 0.1997 | 0.3929 | 0.024* | |
C3 | 0.24286 (19) | 0.4095 (2) | 0.43906 (7) | 0.0200 (4) | |
C4 | 0.2491 (2) | 0.6039 (2) | 0.46562 (7) | 0.0210 (4) | |
H4A | 0.3470 | 0.6540 | 0.4852 | 0.025* | |
C5 | 0.1107 (2) | 0.7207 (2) | 0.46284 (7) | 0.0209 (4) | |
H5A | 0.1136 | 0.8492 | 0.4807 | 0.025* | |
C6 | −0.03402 (19) | 0.6422 (2) | 0.43267 (7) | 0.0190 (4) | |
C7 | −0.1958 (2) | 0.7364 (3) | 0.42384 (7) | 0.0207 (4) | |
C8 | −0.3095 (2) | 0.5888 (2) | 0.38705 (8) | 0.0244 (4) | |
H8A | −0.3491 | 0.6492 | 0.3492 | 0.029* | |
H8B | −0.4016 | 0.5574 | 0.4063 | 0.029* | |
C9 | −0.21166 (19) | 0.3908 (2) | 0.37976 (7) | 0.0203 (4) | |
H9A | −0.2500 | 0.2814 | 0.4033 | 0.024* | |
C10 | −0.22593 (19) | 0.3160 (3) | 0.31726 (7) | 0.0224 (4) | |
C11 | −0.1548 (2) | 0.4245 (3) | 0.27661 (8) | 0.0329 (5) | |
H11A | −0.0954 | 0.5428 | 0.2880 | 0.039* | |
C12 | −0.1708 (3) | 0.3590 (4) | 0.21911 (9) | 0.0444 (6) | |
H12A | −0.1222 | 0.4332 | 0.1923 | 0.053* | |
C13 | −0.2583 (3) | 0.1846 (4) | 0.20172 (9) | 0.0486 (6) | |
H13A | −0.2695 | 0.1413 | 0.1631 | 0.058* | |
C14 | −0.3292 (3) | 0.0744 (3) | 0.24132 (9) | 0.0438 (6) | |
H14A | −0.3887 | −0.0434 | 0.2295 | 0.053* | |
C15 | −0.3120 (2) | 0.1388 (3) | 0.29928 (8) | 0.0313 (5) | |
H15A | −0.3587 | 0.0622 | 0.3261 | 0.038* | |
C16 | 0.3922 (2) | 0.1130 (3) | 0.41791 (9) | 0.0361 (5) | |
H16A | 0.4997 | 0.0572 | 0.4266 | 0.054* | |
H16B | 0.3619 | 0.1258 | 0.3764 | 0.054* | |
H16C | 0.3176 | 0.0227 | 0.4329 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0160 (6) | 0.0255 (7) | 0.0328 (7) | 0.0033 (5) | 0.0025 (5) | −0.0004 (5) |
O2 | 0.0280 (7) | 0.0215 (7) | 0.0327 (7) | 0.0061 (5) | 0.0013 (5) | −0.0043 (5) |
C1 | 0.0197 (9) | 0.0205 (9) | 0.0170 (8) | 0.0005 (7) | 0.0031 (7) | 0.0023 (7) |
C2 | 0.0199 (9) | 0.0191 (9) | 0.0213 (9) | 0.0009 (7) | 0.0041 (7) | −0.0013 (7) |
C3 | 0.0176 (9) | 0.0237 (9) | 0.0191 (8) | 0.0017 (7) | 0.0044 (7) | 0.0050 (7) |
C4 | 0.0174 (8) | 0.0250 (9) | 0.0193 (8) | −0.0036 (7) | −0.0006 (7) | 0.0000 (7) |
C5 | 0.0247 (9) | 0.0202 (9) | 0.0178 (8) | −0.0018 (7) | 0.0031 (7) | −0.0013 (7) |
C6 | 0.0202 (9) | 0.0192 (9) | 0.0178 (8) | −0.0004 (7) | 0.0036 (7) | 0.0014 (7) |
C7 | 0.0215 (9) | 0.0214 (9) | 0.0194 (8) | 0.0015 (7) | 0.0040 (7) | 0.0018 (7) |
C8 | 0.0207 (9) | 0.0256 (10) | 0.0259 (9) | 0.0005 (7) | 0.0009 (7) | −0.0017 (7) |
C9 | 0.0195 (9) | 0.0201 (9) | 0.0207 (9) | 0.0004 (7) | 0.0015 (7) | 0.0002 (7) |
C10 | 0.0164 (8) | 0.0265 (9) | 0.0229 (9) | 0.0055 (7) | −0.0010 (7) | −0.0016 (7) |
C11 | 0.0278 (10) | 0.0425 (12) | 0.0267 (10) | −0.0019 (9) | −0.0003 (8) | 0.0022 (9) |
C12 | 0.0364 (12) | 0.0722 (16) | 0.0248 (11) | 0.0109 (11) | 0.0054 (9) | 0.0059 (10) |
C13 | 0.0468 (14) | 0.0717 (16) | 0.0238 (11) | 0.0224 (12) | −0.0053 (10) | −0.0159 (11) |
C14 | 0.0447 (13) | 0.0421 (12) | 0.0389 (12) | 0.0059 (10) | −0.0110 (10) | −0.0177 (10) |
C15 | 0.0311 (11) | 0.0282 (10) | 0.0322 (10) | 0.0016 (8) | −0.0022 (8) | −0.0059 (8) |
C16 | 0.0224 (10) | 0.0236 (10) | 0.0626 (14) | 0.0045 (8) | 0.0074 (9) | −0.0035 (9) |
O1—C3 | 1.3622 (18) | C8—H8B | 0.9700 |
O1—C16 | 1.427 (2) | C9—C10 | 1.515 (2) |
O2—C7 | 1.2181 (19) | C9—H9A | 0.9800 |
C1—C6 | 1.385 (2) | C10—C11 | 1.384 (2) |
C1—C2 | 1.387 (2) | C10—C15 | 1.386 (2) |
C1—C9 | 1.520 (2) | C11—C12 | 1.386 (3) |
C2—C3 | 1.388 (2) | C11—H11A | 0.9300 |
C2—H2A | 0.9300 | C12—C13 | 1.374 (3) |
C3—C4 | 1.401 (2) | C12—H12A | 0.9300 |
C4—C5 | 1.376 (2) | C13—C14 | 1.370 (3) |
C4—H4A | 0.9300 | C13—H13A | 0.9300 |
C5—C6 | 1.395 (2) | C14—C15 | 1.393 (3) |
C5—H5A | 0.9300 | C14—H14A | 0.9300 |
C6—C7 | 1.469 (2) | C15—H15A | 0.9300 |
C7—C8 | 1.515 (2) | C16—H16A | 0.9600 |
C8—C9 | 1.547 (2) | C16—H16B | 0.9600 |
C8—H8A | 0.9700 | C16—H16C | 0.9600 |
C3—O1—C16 | 117.73 (13) | C10—C9—C8 | 114.08 (13) |
C6—C1—C2 | 120.77 (15) | C1—C9—C8 | 103.19 (13) |
C6—C1—C9 | 111.87 (14) | C10—C9—H9A | 108.4 |
C2—C1—C9 | 127.33 (14) | C1—C9—H9A | 108.4 |
C1—C2—C3 | 118.06 (15) | C8—C9—H9A | 108.4 |
C1—C2—H2A | 121.0 | C11—C10—C15 | 118.44 (16) |
C3—C2—H2A | 121.0 | C11—C10—C9 | 120.72 (16) |
O1—C3—C2 | 124.33 (14) | C15—C10—C9 | 120.84 (16) |
O1—C3—C4 | 114.39 (14) | C10—C11—C12 | 120.84 (19) |
C2—C3—C4 | 121.28 (15) | C10—C11—H11A | 119.6 |
C5—C4—C3 | 120.22 (15) | C12—C11—H11A | 119.6 |
C5—C4—H4A | 119.9 | C13—C12—C11 | 120.1 (2) |
C3—C4—H4A | 119.9 | C13—C12—H12A | 120.0 |
C4—C5—C6 | 118.57 (15) | C11—C12—H12A | 120.0 |
C4—C5—H5A | 120.7 | C14—C13—C12 | 120.01 (19) |
C6—C5—H5A | 120.7 | C14—C13—H13A | 120.0 |
C1—C6—C5 | 121.08 (15) | C12—C13—H13A | 120.0 |
C1—C6—C7 | 110.26 (14) | C13—C14—C15 | 120.0 (2) |
C5—C6—C7 | 128.63 (15) | C13—C14—H14A | 120.0 |
O2—C7—C6 | 126.94 (16) | C15—C14—H14A | 120.0 |
O2—C7—C8 | 125.77 (16) | C10—C15—C14 | 120.59 (19) |
C6—C7—C8 | 107.28 (13) | C10—C15—H15A | 119.7 |
C7—C8—C9 | 106.95 (13) | C14—C15—H15A | 119.7 |
C7—C8—H8A | 110.3 | O1—C16—H16A | 109.5 |
C9—C8—H8A | 110.3 | O1—C16—H16B | 109.5 |
C7—C8—H8B | 110.3 | H16A—C16—H16B | 109.5 |
C9—C8—H8B | 110.3 | O1—C16—H16C | 109.5 |
H8A—C8—H8B | 108.6 | H16A—C16—H16C | 109.5 |
C10—C9—C1 | 113.98 (13) | H16B—C16—H16C | 109.5 |
C6—C1—C2—C3 | 0.1 (2) | C6—C7—C8—C9 | 5.91 (18) |
C9—C1—C2—C3 | −177.78 (15) | C6—C1—C9—C10 | 129.44 (15) |
C16—O1—C3—C2 | 0.6 (2) | C2—C1—C9—C10 | −52.5 (2) |
C16—O1—C3—C4 | −179.31 (14) | C6—C1—C9—C8 | 5.19 (17) |
C1—C2—C3—O1 | −178.98 (14) | C2—C1—C9—C8 | −176.77 (15) |
C1—C2—C3—C4 | 0.9 (2) | C7—C8—C9—C10 | −130.75 (15) |
O1—C3—C4—C5 | 179.27 (14) | C7—C8—C9—C1 | −6.57 (17) |
C2—C3—C4—C5 | −0.6 (2) | C1—C9—C10—C11 | −47.9 (2) |
C3—C4—C5—C6 | −0.7 (2) | C8—C9—C10—C11 | 70.3 (2) |
C2—C1—C6—C5 | −1.4 (2) | C1—C9—C10—C15 | 132.82 (16) |
C9—C1—C6—C5 | 176.78 (14) | C8—C9—C10—C15 | −109.00 (18) |
C2—C1—C6—C7 | −179.85 (14) | C15—C10—C11—C12 | 0.8 (3) |
C9—C1—C6—C7 | −1.66 (18) | C9—C10—C11—C12 | −178.50 (16) |
C4—C5—C6—C1 | 1.7 (2) | C10—C11—C12—C13 | 0.1 (3) |
C4—C5—C6—C7 | 179.80 (15) | C11—C12—C13—C14 | −0.4 (3) |
C1—C6—C7—O2 | 178.15 (16) | C12—C13—C14—C15 | −0.2 (3) |
C5—C6—C7—O2 | −0.1 (3) | C11—C10—C15—C14 | −1.4 (3) |
C1—C6—C7—C8 | −2.76 (18) | C9—C10—C15—C14 | 177.89 (16) |
C5—C6—C7—C8 | 178.95 (16) | C13—C14—C15—C10 | 1.1 (3) |
O2—C7—C8—C9 | −174.98 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.54 | 3.442 (2) | 163 |
C5—H5A···O2ii | 0.93 | 2.50 | 3.344 (2) | 151 |
C16—H16A···O2iii | 0.96 | 2.42 | 3.382 (2) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H14O2 |
Mr | 238.27 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 8.3603 (4), 6.4935 (3), 23.1904 (11) |
β (°) | 99.106 (2) |
V (Å3) | 1243.09 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.36 × 0.19 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.826, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10552, 2548, 1867 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.125, 1.10 |
No. of reflections | 2548 |
No. of parameters | 164 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.25 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···O1i | 0.93 | 2.544 | 3.442 (2) | 163 |
C5—H5A···O2ii | 0.93 | 2.498 | 3.344 (2) | 151 |
C16—H16A···O2iii | 0.96 | 2.424 | 3.382 (2) | 176 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+2, −z+1; (iii) x+1, y−1, z. |
The photochemistry of alkynes is of permanent research interest (Wang et al., 2005). As part of our recent work on photoinduced reactions of aldehydes with alkynes, the title compound was obtained by the reaction of photoexcited 4-methoxybenzaldehyde with trimethylsilyphenylethyne. X-ray structure analysis of the title compound was carried out to elucidate its structure.
Since the atom C9 is chiral and the space group is centrosymmetric, the crystal is a racemate. Bond lengths and angles of the title compound are within normal ranges (Allen et al., 1987). The indane ring is essentially planar with a maximum deviation of 0.053 (2)Å for atom C9. The benzene ring was twisted from the indane ring with the dihedral angle of 81.53 (8)°. The methoxy group attached at the atom C9 is almost coplanar with the indane ring with C16—O1—C3—C4 torsion angle of -179.31 (14)°.
The molecules are linked into chains approximately down the b axis and stabilized by three intermolecular C—H···O interactions (Table 1). These interactions form R23(8) hydrogen bond ring motifs (Bernstein et al., 1995).