The title compound, C25H26O2, was isolated and characterized as a stable intermediate in the conversion of 2,2-diphenylethyl 2,4,6-trimethylphenyl ketone to its formaldehyde-derived enone.
Supporting information
CCDC reference: 259615
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.108
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
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Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
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0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
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1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: APEX2 (Bruker, 2003); cell refinement: APEX2; data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL.
1-Hydroxymethyl-2,2-diphenylethyl 2,4,6-trimethylphenyl ketone
top
Crystal data top
C25H26O2 | F(000) = 768 |
Mr = 358.46 | Dx = 1.199 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7361 (7) Å | Cell parameters from 4193 reflections |
b = 10.5700 (7) Å | θ = 2.5–26.3° |
c = 16.0857 (10) Å | µ = 0.07 mm−1 |
β = 95.574 (3)° | T = 273 K |
V = 1986.0 (2) Å3 | Needle, colorless |
Z = 4 | 0.31 × 0.11 × 0.08 mm |
Data collection top
Bruker X8 APEX CCD area-detector diffractometer | 4054 independent reflections |
Radiation source: fine-focus sealed tube | 3118 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
φ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.991, Tmax = 0.994 | k = −13→13 |
21735 measured reflections | l = −20→20 |
Refinement top
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0451P)2 + 0.8613P] where P = (Fo2 + 2Fc2)/3 |
4054 reflections | (Δ/σ)max < 0.001 |
247 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.28 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.53739 (9) | 1.05594 (10) | 0.22384 (8) | 0.0299 (3) | |
O2 | 0.45430 (12) | 0.90651 (13) | 0.05187 (8) | 0.0420 (3) | |
H1 | 0.4766 | 0.8954 | 0.0049 | 0.050* | |
C1 | 0.55244 (13) | 0.94220 (14) | 0.22668 (9) | 0.0187 (3) | |
C2 | 0.45679 (12) | 0.84942 (14) | 0.19763 (9) | 0.0177 (3) | |
H2 | 0.4625 | 0.7758 | 0.2348 | 0.021* | |
C3 | 0.47773 (13) | 0.80506 (15) | 0.10812 (10) | 0.0233 (3) | |
H3A | 0.5566 | 0.7780 | 0.1072 | 0.028* | |
H3B | 0.4283 | 0.7340 | 0.0918 | 0.028* | |
C4 | 0.33727 (12) | 0.91049 (13) | 0.20102 (9) | 0.0165 (3) | |
H4 | 0.3399 | 0.9934 | 0.1740 | 0.020* | |
C5 | 0.31008 (12) | 0.93454 (14) | 0.29084 (9) | 0.0170 (3) | |
C6 | 0.30950 (12) | 0.83673 (14) | 0.34964 (9) | 0.0200 (3) | |
H6 | 0.3286 | 0.7550 | 0.3346 | 0.024* | |
C7 | 0.28088 (13) | 0.86018 (15) | 0.43002 (10) | 0.0230 (3) | |
H7 | 0.2808 | 0.7943 | 0.4683 | 0.028* | |
C8 | 0.25248 (14) | 0.98172 (16) | 0.45331 (10) | 0.0264 (4) | |
H8 | 0.2337 | 0.9977 | 0.5072 | 0.032* | |
C9 | 0.25240 (15) | 1.07894 (16) | 0.39567 (10) | 0.0282 (4) | |
H9 | 0.2329 | 1.1605 | 0.4108 | 0.034* | |
C10 | 0.28120 (13) | 1.05557 (14) | 0.31534 (10) | 0.0226 (3) | |
H10 | 0.2812 | 1.1219 | 0.2774 | 0.027* | |
C11 | 0.23950 (12) | 0.83673 (14) | 0.15361 (9) | 0.0173 (3) | |
C12 | 0.16040 (13) | 0.90106 (15) | 0.09866 (9) | 0.0223 (3) | |
H12 | 0.1704 | 0.9870 | 0.0892 | 0.027* | |
C13 | 0.06666 (14) | 0.83844 (16) | 0.05773 (10) | 0.0261 (4) | |
H13 | 0.0150 | 0.8827 | 0.0211 | 0.031* | |
C14 | 0.05009 (13) | 0.71090 (16) | 0.07133 (10) | 0.0255 (4) | |
H14 | −0.0127 | 0.6693 | 0.0442 | 0.031* | |
C15 | 0.12801 (13) | 0.64560 (15) | 0.12574 (9) | 0.0230 (3) | |
H15 | 0.1171 | 0.5599 | 0.1354 | 0.028* | |
C16 | 0.22240 (13) | 0.70757 (14) | 0.16597 (9) | 0.0209 (3) | |
H16 | 0.2748 | 0.6624 | 0.2015 | 0.025* | |
C17 | 0.67003 (12) | 0.88962 (13) | 0.25389 (9) | 0.0175 (3) | |
C18 | 0.69148 (13) | 0.82833 (14) | 0.33182 (9) | 0.0190 (3) | |
C19 | 0.80145 (13) | 0.78392 (14) | 0.35581 (9) | 0.0218 (3) | |
H19 | 0.8161 | 0.7451 | 0.4076 | 0.026* | |
C20 | 0.89041 (13) | 0.79560 (15) | 0.30471 (10) | 0.0241 (4) | |
C21 | 0.86743 (13) | 0.85818 (15) | 0.22893 (10) | 0.0237 (3) | |
H21 | 0.9262 | 0.8681 | 0.1946 | 0.028* | |
C22 | 0.75951 (13) | 0.90664 (14) | 0.20254 (9) | 0.0207 (3) | |
C23 | 0.59860 (13) | 0.81012 (16) | 0.38974 (10) | 0.0247 (4) | |
H23A | 0.5533 | 0.7375 | 0.3723 | 0.037* | |
H23B | 0.5506 | 0.8838 | 0.3879 | 0.037* | |
H23C | 0.6330 | 0.7975 | 0.4457 | 0.037* | |
C24 | 1.00746 (15) | 0.7413 (2) | 0.33021 (12) | 0.0395 (5) | |
H24A | 1.0339 | 0.7705 | 0.3852 | 0.059* | |
H24B | 1.0598 | 0.7683 | 0.2914 | 0.059* | |
H24C | 1.0032 | 0.6506 | 0.3302 | 0.059* | |
C25 | 0.74294 (14) | 0.97449 (16) | 0.11907 (10) | 0.0280 (4) | |
H25A | 0.7825 | 1.0540 | 0.1232 | 0.042* | |
H25B | 0.6628 | 0.9890 | 0.1043 | 0.042* | |
H25C | 0.7730 | 0.9233 | 0.0770 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0255 (6) | 0.0146 (6) | 0.0486 (8) | −0.0011 (4) | −0.0017 (5) | −0.0013 (5) |
O2 | 0.0511 (8) | 0.0512 (8) | 0.0260 (7) | 0.0030 (6) | 0.0149 (6) | 0.0098 (6) |
C1 | 0.0225 (8) | 0.0175 (8) | 0.0165 (7) | −0.0013 (6) | 0.0039 (6) | −0.0014 (6) |
C2 | 0.0192 (7) | 0.0141 (7) | 0.0198 (7) | −0.0001 (6) | 0.0014 (6) | 0.0010 (6) |
C3 | 0.0193 (8) | 0.0246 (8) | 0.0259 (8) | −0.0014 (6) | 0.0016 (6) | −0.0038 (6) |
C4 | 0.0195 (8) | 0.0132 (7) | 0.0169 (7) | −0.0003 (6) | 0.0018 (6) | 0.0018 (6) |
C5 | 0.0139 (7) | 0.0189 (7) | 0.0178 (7) | −0.0021 (6) | −0.0004 (6) | 0.0006 (6) |
C6 | 0.0184 (8) | 0.0186 (8) | 0.0227 (8) | −0.0004 (6) | 0.0014 (6) | 0.0005 (6) |
C7 | 0.0227 (8) | 0.0255 (8) | 0.0205 (8) | −0.0048 (6) | 0.0010 (6) | 0.0051 (6) |
C8 | 0.0306 (9) | 0.0315 (9) | 0.0180 (8) | −0.0067 (7) | 0.0070 (6) | −0.0047 (7) |
C9 | 0.0360 (10) | 0.0219 (8) | 0.0277 (9) | 0.0006 (7) | 0.0079 (7) | −0.0049 (7) |
C10 | 0.0275 (8) | 0.0184 (8) | 0.0222 (8) | 0.0005 (6) | 0.0030 (6) | 0.0020 (6) |
C11 | 0.0186 (7) | 0.0190 (7) | 0.0147 (7) | 0.0002 (6) | 0.0045 (6) | −0.0012 (6) |
C12 | 0.0261 (8) | 0.0189 (8) | 0.0216 (8) | 0.0020 (6) | 0.0013 (6) | 0.0011 (6) |
C13 | 0.0242 (8) | 0.0302 (9) | 0.0229 (8) | 0.0064 (7) | −0.0035 (7) | −0.0004 (7) |
C14 | 0.0196 (8) | 0.0334 (9) | 0.0236 (8) | −0.0035 (7) | 0.0017 (6) | −0.0073 (7) |
C15 | 0.0266 (8) | 0.0208 (8) | 0.0226 (8) | −0.0045 (6) | 0.0066 (6) | −0.0021 (6) |
C16 | 0.0221 (8) | 0.0209 (8) | 0.0196 (8) | 0.0019 (6) | 0.0008 (6) | 0.0013 (6) |
C17 | 0.0189 (8) | 0.0133 (7) | 0.0202 (7) | −0.0020 (6) | 0.0011 (6) | −0.0050 (6) |
C18 | 0.0207 (8) | 0.0173 (7) | 0.0188 (7) | −0.0033 (6) | 0.0013 (6) | −0.0057 (6) |
C19 | 0.0243 (8) | 0.0224 (8) | 0.0179 (8) | 0.0007 (6) | −0.0015 (6) | −0.0034 (6) |
C20 | 0.0199 (8) | 0.0271 (9) | 0.0248 (8) | 0.0002 (6) | −0.0004 (6) | −0.0086 (7) |
C21 | 0.0210 (8) | 0.0267 (9) | 0.0240 (8) | −0.0046 (6) | 0.0061 (6) | −0.0070 (7) |
C22 | 0.0238 (8) | 0.0164 (7) | 0.0221 (8) | −0.0037 (6) | 0.0030 (6) | −0.0048 (6) |
C23 | 0.0238 (8) | 0.0309 (9) | 0.0194 (8) | −0.0033 (7) | 0.0017 (6) | −0.0011 (6) |
C24 | 0.0243 (9) | 0.0618 (13) | 0.0319 (10) | 0.0094 (9) | 0.0007 (7) | −0.0019 (9) |
C25 | 0.0304 (9) | 0.0270 (9) | 0.0278 (9) | −0.0014 (7) | 0.0086 (7) | 0.0041 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.2153 (18) | C13—C14 | 1.382 (2) |
O2—C3 | 1.413 (2) | C13—H13 | 0.9300 |
O2—H1 | 0.8311 | C14—C15 | 1.387 (2) |
C1—C17 | 1.512 (2) | C14—H14 | 0.9300 |
C1—C2 | 1.529 (2) | C15—C16 | 1.391 (2) |
C2—C4 | 1.550 (2) | C15—H15 | 0.9300 |
C2—C3 | 1.556 (2) | C16—H16 | 0.9300 |
C2—H2 | 0.9800 | C17—C22 | 1.409 (2) |
C3—H3A | 0.9700 | C17—C18 | 1.412 (2) |
C3—H3B | 0.9700 | C18—C19 | 1.392 (2) |
C4—C11 | 1.528 (2) | C18—C23 | 1.513 (2) |
C4—C5 | 1.531 (2) | C19—C20 | 1.396 (2) |
C4—H4 | 0.9800 | C19—H19 | 0.9300 |
C5—C10 | 1.390 (2) | C20—C21 | 1.390 (2) |
C5—C6 | 1.402 (2) | C20—C24 | 1.508 (2) |
C6—C7 | 1.389 (2) | C21—C22 | 1.394 (2) |
C6—H6 | 0.9300 | C21—H21 | 0.9300 |
C7—C8 | 1.388 (2) | C22—C25 | 1.518 (2) |
C7—H7 | 0.9300 | C23—H23A | 0.9600 |
C8—C9 | 1.384 (2) | C23—H23B | 0.9600 |
C8—H8 | 0.9300 | C23—H23C | 0.9600 |
C9—C10 | 1.389 (2) | C24—H24A | 0.9600 |
C9—H9 | 0.9300 | C24—H24B | 0.9600 |
C10—H10 | 0.9300 | C24—H24C | 0.9600 |
C11—C12 | 1.395 (2) | C25—H25A | 0.9600 |
C11—C16 | 1.397 (2) | C25—H25B | 0.9600 |
C12—C13 | 1.393 (2) | C25—H25C | 0.9600 |
C12—H12 | 0.9300 | | |
| | | |
C3—O2—H1 | 114.54 | C14—C13—H13 | 119.8 |
O1—C1—C17 | 119.98 (13) | C12—C13—H13 | 119.8 |
O1—C1—C2 | 121.54 (13) | C13—C14—C15 | 119.40 (14) |
C17—C1—C2 | 118.35 (12) | C13—C14—H14 | 120.3 |
C1—C2—C4 | 111.24 (11) | C15—C14—H14 | 120.3 |
C1—C2—C3 | 107.39 (12) | C14—C15—C16 | 120.38 (14) |
C4—C2—C3 | 112.51 (12) | C14—C15—H15 | 119.8 |
C1—C2—H2 | 108.5 | C16—C15—H15 | 119.8 |
C4—C2—H2 | 108.5 | C15—C16—C11 | 120.85 (14) |
C3—C2—H2 | 108.5 | C15—C16—H16 | 119.6 |
O2—C3—C2 | 108.99 (12) | C11—C16—H16 | 119.6 |
O2—C3—H3A | 109.9 | C22—C17—C18 | 120.01 (14) |
C2—C3—H3A | 109.9 | C22—C17—C1 | 119.63 (13) |
O2—C3—H3B | 109.9 | C18—C17—C1 | 120.30 (13) |
C2—C3—H3B | 109.9 | C19—C18—C17 | 118.78 (13) |
H3A—C3—H3B | 108.3 | C19—C18—C23 | 119.36 (14) |
C11—C4—C5 | 109.90 (11) | C17—C18—C23 | 121.87 (13) |
C11—C4—C2 | 114.09 (11) | C18—C19—C20 | 122.23 (15) |
C5—C4—C2 | 112.01 (11) | C18—C19—H19 | 118.9 |
C11—C4—H4 | 106.8 | C20—C19—H19 | 118.9 |
C5—C4—H4 | 106.8 | C21—C20—C19 | 117.78 (14) |
C2—C4—H4 | 106.8 | C21—C20—C24 | 120.89 (15) |
C10—C5—C6 | 118.04 (13) | C19—C20—C24 | 121.33 (15) |
C10—C5—C4 | 119.95 (13) | C20—C21—C22 | 122.35 (14) |
C6—C5—C4 | 121.97 (13) | C20—C21—H21 | 118.8 |
C7—C6—C5 | 120.92 (14) | C22—C21—H21 | 118.8 |
C7—C6—H6 | 119.5 | C21—C22—C17 | 118.79 (14) |
C5—C6—H6 | 119.5 | C21—C22—C25 | 118.53 (14) |
C8—C7—C6 | 120.16 (14) | C17—C22—C25 | 122.68 (14) |
C8—C7—H7 | 119.9 | C18—C23—H23A | 109.5 |
C6—C7—H7 | 119.9 | C18—C23—H23B | 109.5 |
C9—C8—C7 | 119.40 (14) | H23A—C23—H23B | 109.5 |
C9—C8—H8 | 120.3 | C18—C23—H23C | 109.5 |
C7—C8—H8 | 120.3 | H23A—C23—H23C | 109.5 |
C8—C9—C10 | 120.45 (15) | H23B—C23—H23C | 109.5 |
C8—C9—H9 | 119.8 | C20—C24—H24A | 109.5 |
C10—C9—H9 | 119.8 | C20—C24—H24B | 109.5 |
C9—C10—C5 | 121.02 (14) | H24A—C24—H24B | 109.5 |
C9—C10—H10 | 119.5 | C20—C24—H24C | 109.5 |
C5—C10—H10 | 119.5 | H24A—C24—H24C | 109.5 |
C12—C11—C16 | 118.07 (14) | H24B—C24—H24C | 109.5 |
C12—C11—C4 | 119.25 (13) | C22—C25—H25A | 109.5 |
C16—C11—C4 | 122.60 (13) | C22—C25—H25B | 109.5 |
C13—C12—C11 | 120.94 (14) | H25A—C25—H25B | 109.5 |
C13—C12—H12 | 119.5 | C22—C25—H25C | 109.5 |
C11—C12—H12 | 119.5 | H25A—C25—H25C | 109.5 |
C14—C13—C12 | 120.35 (14) | H25B—C25—H25C | 109.5 |
| | | |
C22—C17—C1—O1 | −68.0 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O2i | 0.8311 | 2.4541 | 2.862 (2) | 111.20 (9) |
Symmetry code: (i) −x+1, −y+2, −z. |