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In the title mol­ecule, C29H26O, the two methyl substituents on the benzene rings are sterically hindered and influence the structure of the mol­ecule and its photochemical properties. The dihedral angle between the two benzene ring planes is 80.2 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048136/wn2081sup1.cif
Contains datablocks global, VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048136/wn2081VIsup2.hkl
Contains datablock VI

CCDC reference: 630502

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.049
  • wR factor = 0.146
  • Data-to-parameter ratio = 18.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT048_ALERT_1_C MoietyFormula Not Given ........................ ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C10 .. 5.30 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2, (Bruker 2004); cell refinement: APEX2; data reduction: SAINT, (Bruker 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2004); software used to prepare material for publication: SHELXTL.

(VI) top
Crystal data top
C29H26OF(000) = 832
Mr = 390.50Dx = 1.174 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.5290 (8) ÅCell parameters from 2527 reflections
b = 11.3445 (8) Åθ = 2.5–21.8°
c = 16.9415 (12) ŵ = 0.07 mm1
β = 94.124 (1)°T = 291 K
V = 2210.1 (3) Å3Block, colourless
Z = 40.35 × 0.18 × 0.09 mm
Data collection top
Bruker ApexII CCD area-detector
diffractometer
5053 independent reflections
Radiation source: fine-focus sealed tube3024 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)
h = 1414
Tmin = 0.976, Tmax = 0.994k = 1414
13103 measured reflectionsl = 1221
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.065P)2 + 0.2364P]
where P = (Fo2 + 2Fc2)/3
5053 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.16 e Å3
Special details top

Experimental. IR spectra were obtained on a Shimadzu-IR 435 spectrometer. 1H-NMR spectra were recorded on a Bruker AC–P200 spectrometer with TMS as the internal standard. Elemental analysis was performed on a Yanaco MT-3 instrument. Melting points were determined with a model Yanaco MP-500 apparatus and uncorrected.

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
xyzUiso*/Ueq
O10.05573 (9)0.52133 (10)0.22760 (7)0.0499 (3)
C10.02356 (14)0.70141 (14)0.28369 (10)0.0471 (4)
C20.00158 (15)0.81414 (15)0.31856 (10)0.0501 (4)
C30.09189 (18)0.88901 (16)0.34917 (12)0.0638 (5)
H30.16900.86640.34610.077*
C40.0671 (2)0.99450 (19)0.38335 (14)0.0786 (6)
H40.12771.04290.40290.094*
C50.0481 (2)1.03080 (19)0.38940 (13)0.0786 (6)
H50.06361.10290.41250.094*
C60.13680 (19)0.96044 (17)0.36139 (12)0.0664 (5)
H60.21310.98440.36600.080*
C70.11483 (15)0.85058 (15)0.32505 (10)0.0526 (4)
C80.20620 (16)0.77609 (17)0.29728 (11)0.0599 (5)
H80.28270.80090.30010.072*
C90.18454 (15)0.66785 (17)0.26615 (11)0.0571 (5)
H90.24590.61900.24860.069*
C100.07002 (14)0.63104 (15)0.26090 (10)0.0469 (4)
C110.13810 (14)0.65912 (16)0.26738 (11)0.0548 (5)
H110.20140.71020.27120.066*
C120.15246 (15)0.54795 (16)0.24703 (11)0.0547 (5)
H120.22460.52320.23200.066*
C130.05385 (13)0.46006 (15)0.24772 (10)0.0463 (4)
C140.05931 (13)0.36723 (15)0.18275 (10)0.0473 (4)
C150.08758 (15)0.40152 (17)0.10790 (11)0.0568 (5)
H150.10490.48030.09900.068*
C160.09075 (16)0.32194 (19)0.04607 (10)0.0601 (5)
C170.06515 (15)0.20493 (18)0.06114 (11)0.0603 (5)
H170.06810.15020.02050.072*
C180.03534 (15)0.16678 (17)0.13457 (11)0.0553 (5)
C190.03291 (14)0.24949 (16)0.19521 (10)0.0508 (4)
H190.01320.22540.24500.061*
C200.1227 (2)0.3622 (2)0.03457 (12)0.0925 (8)
H20A0.20520.35580.03770.139*
H20B0.09940.44280.04270.139*
H20C0.08370.31370.07460.139*
C210.0056 (2)0.03991 (19)0.14847 (14)0.0859 (7)
H21A0.07310.02510.12860.129*
H21B0.01360.02350.20420.129*
H21C0.05730.00990.12160.129*
C220.05351 (14)0.40690 (14)0.33044 (9)0.0439 (4)
C230.15580 (15)0.35773 (16)0.36443 (10)0.0527 (4)
H230.22150.35620.33570.063*
C240.16198 (16)0.31105 (17)0.44007 (11)0.0593 (5)
C250.06333 (17)0.31587 (16)0.48215 (11)0.0602 (5)
H250.06690.28610.53340.072*
C260.03954 (16)0.36308 (15)0.45067 (10)0.0520 (4)
C270.04380 (14)0.40774 (14)0.37397 (10)0.0478 (4)
H270.11320.43870.35150.057*
C280.14498 (18)0.36910 (19)0.49831 (13)0.0733 (6)
H28A0.15820.29330.52120.110*
H28B0.21170.39130.46440.110*
H28C0.13210.42650.53970.110*
C290.2750 (2)0.2597 (2)0.47629 (15)0.0917 (7)
H29A0.30970.31370.51470.138*
H29B0.32720.24660.43550.138*
H29C0.25950.18620.50160.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0460 (6)0.0500 (7)0.0535 (7)0.0046 (5)0.0024 (5)0.0049 (6)
C10.0486 (9)0.0466 (10)0.0460 (9)0.0020 (7)0.0041 (8)0.0073 (8)
C20.0592 (10)0.0445 (10)0.0467 (10)0.0009 (8)0.0050 (8)0.0103 (8)
C30.0706 (12)0.0522 (12)0.0686 (13)0.0117 (9)0.0046 (10)0.0054 (10)
C40.0965 (17)0.0574 (13)0.0816 (16)0.0184 (12)0.0034 (13)0.0055 (11)
C50.1078 (18)0.0524 (13)0.0753 (15)0.0008 (12)0.0057 (13)0.0086 (11)
C60.0858 (14)0.0528 (12)0.0610 (12)0.0136 (10)0.0082 (11)0.0021 (10)
C70.0631 (11)0.0469 (10)0.0476 (10)0.0054 (8)0.0027 (9)0.0062 (8)
C80.0508 (10)0.0636 (12)0.0649 (12)0.0143 (9)0.0023 (9)0.0026 (10)
C90.0468 (10)0.0617 (12)0.0619 (12)0.0009 (8)0.0023 (8)0.0068 (9)
C100.0484 (9)0.0485 (10)0.0443 (9)0.0057 (7)0.0061 (7)0.0031 (8)
C110.0472 (10)0.0544 (11)0.0639 (12)0.0046 (8)0.0106 (8)0.0067 (9)
C120.0464 (10)0.0585 (12)0.0605 (12)0.0008 (8)0.0129 (8)0.0037 (9)
C130.0408 (9)0.0502 (10)0.0483 (10)0.0070 (7)0.0055 (7)0.0006 (8)
C140.0434 (9)0.0555 (11)0.0436 (9)0.0079 (7)0.0063 (7)0.0014 (8)
C150.0579 (11)0.0612 (12)0.0526 (11)0.0125 (8)0.0127 (9)0.0100 (9)
C160.0576 (11)0.0799 (14)0.0435 (10)0.0212 (10)0.0086 (8)0.0035 (10)
C170.0594 (11)0.0766 (14)0.0446 (10)0.0181 (10)0.0015 (9)0.0133 (10)
C180.0577 (10)0.0599 (11)0.0481 (10)0.0066 (8)0.0017 (8)0.0077 (9)
C190.0537 (10)0.0579 (11)0.0412 (9)0.0035 (8)0.0063 (8)0.0009 (8)
C200.1180 (19)0.111 (2)0.0521 (12)0.0354 (15)0.0294 (13)0.0159 (13)
C210.1142 (19)0.0673 (15)0.0762 (15)0.0059 (13)0.0060 (14)0.0164 (12)
C220.0473 (9)0.0424 (9)0.0422 (9)0.0013 (7)0.0045 (7)0.0065 (7)
C230.0501 (10)0.0587 (11)0.0492 (10)0.0039 (8)0.0036 (8)0.0071 (9)
C240.0652 (12)0.0565 (11)0.0549 (11)0.0018 (9)0.0060 (9)0.0014 (9)
C250.0778 (13)0.0564 (11)0.0460 (10)0.0079 (10)0.0016 (10)0.0030 (9)
C260.0629 (11)0.0433 (9)0.0509 (10)0.0118 (8)0.0125 (9)0.0056 (8)
C270.0484 (9)0.0453 (9)0.0502 (10)0.0022 (7)0.0062 (8)0.0042 (8)
C280.0821 (14)0.0736 (14)0.0678 (13)0.0191 (11)0.0306 (11)0.0039 (11)
C290.0828 (15)0.1089 (19)0.0803 (16)0.0183 (14)0.0169 (13)0.0139 (14)
Geometric parameters (Å, º) top
O1—C101.381 (2)C16—C171.388 (3)
O1—C131.4607 (19)C16—C201.511 (3)
C1—C101.375 (2)C17—C181.384 (3)
C1—C21.439 (2)C17—H170.9300
C1—C111.450 (2)C18—C191.393 (2)
C2—C31.413 (2)C18—C211.502 (3)
C2—C71.416 (2)C19—H190.9300
C3—C41.369 (3)C20—H20A0.9600
C3—H30.9300C20—H20B0.9600
C4—C51.401 (3)C20—H20C0.9600
C4—H40.9300C21—H21A0.9600
C5—C61.356 (3)C21—H21B0.9600
C5—H50.9300C21—H21C0.9600
C6—C71.421 (3)C22—C271.386 (2)
C6—H60.9300C22—C231.391 (2)
C7—C81.405 (3)C23—C241.384 (2)
C8—C91.366 (2)C23—H230.9300
C8—H80.9300C24—C251.386 (3)
C9—C101.394 (2)C24—C291.516 (3)
C9—H90.9300C25—C261.374 (3)
C11—C121.321 (2)C25—H250.9300
C11—H110.9300C26—C271.392 (2)
C12—C131.513 (2)C26—C281.508 (2)
C12—H120.9300C27—H270.9300
C13—C221.526 (2)C28—H28A0.9600
C13—C141.528 (2)C28—H28B0.9600
C14—C151.387 (2)C28—H28C0.9600
C14—C191.389 (2)C29—H29A0.9600
C15—C161.385 (3)C29—H29B0.9600
C15—H150.9300C29—H29C0.9600
C10—O1—C13117.39 (12)C18—C17—C16122.32 (17)
C10—C1—C2118.27 (15)C18—C17—H17118.8
C10—C1—C11117.48 (15)C16—C17—H17118.8
C2—C1—C11124.19 (15)C17—C18—C19118.15 (18)
C3—C2—C7118.26 (17)C17—C18—C21120.99 (18)
C3—C2—C1122.55 (16)C19—C18—C21120.86 (18)
C7—C2—C1119.16 (15)C14—C19—C18121.28 (16)
C4—C3—C2120.7 (2)C14—C19—H19119.4
C4—C3—H3119.7C18—C19—H19119.4
C2—C3—H3119.7C16—C20—H20A109.5
C3—C4—C5121.1 (2)C16—C20—H20B109.5
C3—C4—H4119.5H20A—C20—H20B109.5
C5—C4—H4119.5C16—C20—H20C109.5
C6—C5—C4119.8 (2)H20A—C20—H20C109.5
C6—C5—H5120.1H20B—C20—H20C109.5
C4—C5—H5120.1C18—C21—H21A109.5
C5—C6—C7121.0 (2)C18—C21—H21B109.5
C5—C6—H6119.5H21A—C21—H21B109.5
C7—C6—H6119.5C18—C21—H21C109.5
C8—C7—C2119.36 (16)H21A—C21—H21C109.5
C8—C7—C6121.33 (17)H21B—C21—H21C109.5
C2—C7—C6119.29 (17)C27—C22—C23118.49 (15)
C9—C8—C7121.08 (17)C27—C22—C13122.79 (14)
C9—C8—H8119.5C23—C22—C13118.71 (14)
C7—C8—H8119.5C24—C23—C22121.49 (16)
C8—C9—C10119.61 (17)C24—C23—H23119.3
C8—C9—H9120.2C22—C23—H23119.3
C10—C9—H9120.2C23—C24—C25118.15 (17)
C1—C10—O1121.58 (14)C23—C24—C29120.50 (18)
C1—C10—C9122.41 (16)C25—C24—C29121.33 (18)
O1—C10—C9115.94 (15)C26—C25—C24122.22 (17)
C12—C11—C1119.90 (16)C26—C25—H25118.9
C12—C11—H11120.1C24—C25—H25118.9
C1—C11—H11120.1C25—C26—C27118.41 (16)
C11—C12—C13121.26 (15)C25—C26—C28121.10 (17)
C11—C12—H12119.4C27—C26—C28120.49 (17)
C13—C12—H12119.4C22—C27—C26121.23 (16)
O1—C13—C12108.81 (14)C22—C27—H27119.4
O1—C13—C22110.06 (12)C26—C27—H27119.4
C12—C13—C22108.61 (14)C26—C28—H28A109.5
O1—C13—C14103.87 (12)C26—C28—H28B109.5
C12—C13—C14112.26 (13)H28A—C28—H28B109.5
C22—C13—C14113.09 (14)C26—C28—H28C109.5
C15—C14—C19118.48 (16)H28A—C28—H28C109.5
C15—C14—C13119.32 (16)H28B—C28—H28C109.5
C19—C14—C13122.16 (15)C24—C29—H29A109.5
C16—C15—C14121.95 (18)C24—C29—H29B109.5
C16—C15—H15119.0H29A—C29—H29B109.5
C14—C15—H15119.0C24—C29—H29C109.5
C15—C16—C17117.82 (17)H29A—C29—H29C109.5
C15—C16—C20120.5 (2)H29B—C29—H29C109.5
C17—C16—C20121.64 (19)
C10—C1—C2—C3175.23 (16)C12—C13—C14—C1541.6 (2)
C11—C1—C2—C37.9 (3)C22—C13—C14—C15164.93 (14)
C10—C1—C2—C72.7 (2)O1—C13—C14—C19101.94 (17)
C11—C1—C2—C7174.23 (16)C12—C13—C14—C19140.68 (16)
C7—C2—C3—C40.7 (3)C22—C13—C14—C1917.4 (2)
C1—C2—C3—C4178.63 (18)C19—C14—C15—C160.4 (2)
C2—C3—C4—C50.4 (3)C13—C14—C15—C16178.19 (15)
C3—C4—C5—C60.3 (3)C14—C15—C16—C170.3 (3)
C4—C5—C6—C70.7 (3)C14—C15—C16—C20179.60 (17)
C3—C2—C7—C8178.05 (16)C15—C16—C17—C181.0 (3)
C1—C2—C7—C80.1 (2)C20—C16—C17—C18179.74 (18)
C3—C2—C7—C60.3 (2)C16—C17—C18—C190.9 (3)
C1—C2—C7—C6178.32 (15)C16—C17—C18—C21178.66 (18)
C5—C6—C7—C8178.72 (19)C15—C14—C19—C180.5 (2)
C5—C6—C7—C20.4 (3)C13—C14—C19—C18178.23 (15)
C2—C7—C8—C91.8 (3)C17—C18—C19—C140.1 (3)
C6—C7—C8—C9176.53 (17)C21—C18—C19—C14179.44 (18)
C7—C8—C9—C100.8 (3)O1—C13—C22—C276.6 (2)
C2—C1—C10—O1179.47 (14)C12—C13—C22—C27125.63 (16)
C11—C1—C10—O13.4 (2)C14—C13—C22—C27109.06 (17)
C2—C1—C10—C93.8 (3)O1—C13—C22—C23171.95 (14)
C11—C1—C10—C9173.28 (16)C12—C13—C22—C2352.9 (2)
C13—O1—C10—C126.3 (2)C14—C13—C22—C2372.38 (19)
C13—O1—C10—C9156.81 (15)C27—C22—C23—C240.4 (3)
C8—C9—C10—C12.1 (3)C13—C22—C23—C24178.21 (16)
C8—C9—C10—O1179.03 (15)C22—C23—C24—C250.9 (3)
C10—C1—C11—C1213.8 (3)C22—C23—C24—C29179.05 (18)
C2—C1—C11—C12169.33 (17)C23—C24—C25—C261.2 (3)
C1—C11—C12—C135.8 (3)C29—C24—C25—C26179.38 (19)
C10—O1—C13—C1241.72 (18)C24—C25—C26—C270.2 (3)
C10—O1—C13—C2277.18 (17)C24—C25—C26—C28178.93 (17)
C10—O1—C13—C14161.47 (13)C23—C22—C27—C261.4 (2)
C11—C12—C13—O132.4 (2)C13—C22—C27—C26177.12 (15)
C11—C12—C13—C2287.4 (2)C25—C26—C27—C221.1 (2)
C11—C12—C13—C14146.79 (17)C28—C26—C27—C22177.57 (15)
O1—C13—C14—C1575.78 (17)
 

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