Download citation
Download citation
link to html
We report the crystal structure of rubrene, C42H28 (5,6,11,12-tetraphenyltetracene), in the temperature interval 100-300 K. The crystals are grown by physical vapor transport in an open system. The crystal structure is orthorhombic over the entire temperature range.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106003053/bk5027sup1.cif
Contains datablocks CP995, 100K, 125K, 150K, 175K, 200K, 235K, 275K, 293K

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995sup2.fcf
Contains datablocks CP995, CP995

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995bsup3.fcf
Contains datablock CP995B

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995csup4.fcf
Contains datablocks CP995C, CP995C

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995dsup5.fcf
Contains datablocks CP995D, CP995D

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995esup6.fcf
Contains datablocks CP995E, CP995E

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995fsup7.fcf
Contains datablocks CP995F, CP995F

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995gsup8.fcf
Contains datablocks CP995G, CP995G

fcf

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106003053/bk5027cp995hsup9.fcf
Contains datablocks CP995H, CP995H

CCDC references: 605647; 605648; 605649; 605650; 605651; 605652; 605653; 605654

Computing details top

For all compounds, data collection: SMART, Bruker Version 5.624, 2001; cell refinement: SAINT, Bruker Version 6.02A, 2000; data reduction: XPREP, Bruker Version 5.1/NT, 2000. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for 100K, 293K; SIR97 (Altomare et al., 1999) for 125K, 150K, 175K, 200K, 235K, 275K. For all compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTO (Meetsma, 2004) PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
(100K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 4621 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.296 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 4621 reflections
a = 26.789 (4) Åθ = 2.9–29.3°
b = 7.170 (1) ŵ = 0.07 mm1
c = 14.211 (2) ÅT = 100 K
V = 2729.6 (7) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1424 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1201 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.035
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.0°
phi and ω scansh = 3133
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 88
Tmin = 0.952, Tmax = 0.998l = 1717
10125 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: difference Fourier map
wR(F2) = 0.099All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0473P)2 + 2.3678P]
where P = (Fo2 + 2Fc2)/3
1424 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C42H28V = 2729.6 (7) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.789 (4) ŵ = 0.07 mm1
b = 7.170 (1) ÅT = 100 K
c = 14.211 (2) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1424 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
1201 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.998Rint = 0.035
10125 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.099All H-atom parameters refined
S = 1.06Δρmax = 0.26 e Å3
1424 reflectionsΔρmin = 0.21 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02737 (6)0.000000.000000.0135 (5)
C20.05314 (5)0.14464 (16)0.04914 (8)0.0141 (3)
C30.02678 (5)0.29578 (16)0.08755 (8)0.0142 (4)
C40.05191 (5)0.44754 (17)0.13412 (9)0.0170 (4)
C50.02646 (5)0.58934 (17)0.17534 (9)0.0186 (4)
C60.10760 (5)0.13448 (16)0.07274 (8)0.0148 (3)
C70.14292 (5)0.24817 (18)0.02881 (9)0.0185 (4)
C80.19199 (5)0.25089 (19)0.05979 (10)0.0225 (4)
C90.20685 (5)0.1389 (2)0.13448 (10)0.0244 (4)
C100.17219 (5)0.0251 (2)0.17857 (10)0.0233 (4)
C110.12302 (5)0.02362 (18)0.14816 (9)0.0189 (4)
H40.0883 (5)0.447 (2)0.1357 (10)0.016 (4)*
H50.0438 (5)0.689 (2)0.2065 (10)0.020 (4)*
H70.1328 (5)0.327 (2)0.0256 (10)0.021 (4)*
H80.2167 (5)0.332 (2)0.0279 (11)0.028 (4)*
H90.2413 (6)0.140 (2)0.1546 (10)0.025 (4)*
H100.1825 (6)0.054 (2)0.2311 (12)0.032 (4)*
H110.0978 (5)0.054 (2)0.1804 (11)0.021 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0166 (9)0.0122 (8)0.0116 (8)0.00000.00000.0017 (6)
C20.0164 (6)0.0132 (6)0.0127 (6)0.0011 (5)0.0009 (4)0.0021 (5)
C30.0191 (7)0.0129 (6)0.0107 (6)0.0017 (5)0.0002 (5)0.0018 (5)
C40.0198 (7)0.0155 (6)0.0156 (6)0.0032 (5)0.0006 (5)0.0005 (5)
C50.0265 (7)0.0129 (6)0.0163 (6)0.0041 (5)0.0004 (5)0.0014 (5)
C60.0165 (6)0.0134 (6)0.0145 (6)0.0001 (5)0.0002 (5)0.0042 (5)
C70.0200 (7)0.0148 (6)0.0206 (7)0.0003 (5)0.0024 (5)0.0011 (5)
C80.0184 (7)0.0206 (7)0.0286 (7)0.0027 (5)0.0051 (5)0.0044 (6)
C90.0148 (7)0.0302 (8)0.0282 (7)0.0010 (5)0.0033 (6)0.0085 (6)
C100.0244 (7)0.0265 (7)0.0191 (7)0.0033 (6)0.0051 (5)0.0008 (6)
C110.0214 (7)0.0191 (6)0.0162 (6)0.0016 (5)0.0013 (5)0.0003 (5)
Geometric parameters (Å, º) top
C1—C21.4282 (14)C7—C81.3864 (19)
C1—C2i1.4282 (14)C8—C91.389 (2)
C1—C1ii1.466 (2)C9—C101.386 (2)
C2—C31.4039 (17)C10—C111.3863 (19)
C2—C61.4988 (19)C4—H40.975 (13)
C3—C41.4406 (17)C5—H50.961 (14)
C3—C3iii1.4348 (19)C7—H70.995 (14)
C4—C51.3571 (18)C8—H80.991 (14)
C5—C5iii1.4177 (19)C9—H90.966 (16)
C6—C71.3962 (18)C10—H100.977 (16)
C6—C111.3969 (17)C11—H110.988 (14)
C2···C11i3.5807 (18)C9···H10vi2.987 (16)
C4···C73.1980 (19)C9···H8iv3.092 (15)
C4···C113.5927 (19)C11···H7i3.070 (14)
C6···C6i2.8272 (17)H4···C62.468 (14)
C6···C11i3.3631 (18)H4···C72.546 (14)
C6···C7i3.2412 (18)H4···H7vii2.55 (2)
C7···C43.1980 (19)H5···H11viii2.37 (2)
C7···C6i3.2412 (18)H5···C3vi3.059 (14)
C7···C11i3.2259 (19)H5···C4vi2.935 (14)
C8···C8iv3.542 (2)H7···C7vii3.058 (14)
C11···C43.5927 (19)H7···C11i3.070 (14)
C11···C6i3.3631 (18)H7···H4vii2.55 (2)
C11···C2i3.5807 (18)H7···H7vii2.59 (2)
C11···C7i3.2259 (19)H8···H8vii2.54 (2)
C3···H5v3.059 (14)H8···C8iv2.809 (14)
C4···H5v2.935 (14)H8···C9iv3.092 (15)
C4···H11vi2.909 (15)H8···H8iv2.28 (2)
C5···H11vi2.985 (15)H10···C9v2.987 (16)
C6···H42.468 (14)H11···H5ix2.37 (2)
C7···H42.546 (14)H11···C4v2.909 (15)
C7···H7vii3.058 (14)H11···C5v2.985 (15)
C8···H8iv2.809 (14)
C2—C1—C2i122.19 (13)C9—C10—C11120.01 (13)
C1ii—C1—C2118.91 (8)C6—C11—C10121.05 (12)
C1ii—C1—C2i118.91 (8)C3—C4—H4118.3 (8)
C1—C2—C3120.50 (12)C5—C4—H4119.7 (8)
C1—C2—C6123.00 (11)C4—C5—H5120.9 (8)
C3—C2—C6116.11 (10)C5iii—C5—H5118.9 (8)
C2—C3—C4121.78 (12)C6—C7—H7119.6 (8)
C2—C3—C3iii120.20 (11)C8—C7—H7119.8 (8)
C3iii—C3—C4117.86 (11)C7—C8—H8119.8 (8)
C3—C4—C5121.97 (12)C9—C8—H8119.8 (8)
C4—C5—C5iii120.16 (12)C8—C9—H9119.7 (9)
C2—C6—C7122.09 (11)C10—C9—H9120.7 (9)
C2—C6—C11119.16 (11)C9—C10—H10119.9 (9)
C7—C6—C11118.35 (12)C11—C10—H10120.1 (9)
C6—C7—C8120.58 (12)C6—C11—H11118.3 (8)
C7—C8—C9120.41 (12)C10—C11—H11120.6 (8)
C8—C9—C10119.59 (12)
C2i—C1—C2—C3172.76 (9)C2—C3—C3iii—C2iii0.00 (17)
C2i—C1—C2—C614.70 (13)C2—C3—C3iii—C4iii175.43 (11)
C1ii—C1—C2—C37.24 (12)C4—C3—C3iii—C2iii175.43 (11)
C1ii—C1—C2—C6165.30 (8)C4—C3—C3iii—C4iii0.00 (16)
C1—C2—C3—C4177.42 (10)C3—C4—C5—C5iii1.42 (19)
C1—C2—C3—C3iii7.34 (16)C4—C5—C5iii—C4iii0.00 (19)
C6—C2—C3—C49.54 (16)C2—C6—C7—C8172.44 (12)
C6—C2—C3—C3iii165.71 (10)C11—C6—C7—C80.22 (18)
C1—C2—C6—C7110.05 (13)C2—C6—C11—C10173.26 (12)
C1—C2—C6—C1177.35 (14)C7—C6—C11—C100.37 (19)
C3—C2—C6—C777.11 (15)C6—C7—C8—C90.7 (2)
C3—C2—C6—C1195.50 (14)C7—C8—C9—C100.5 (2)
C2—C3—C4—C5176.74 (12)C8—C9—C10—C110.1 (2)
C3iii—C3—C4—C51.39 (18)C9—C10—C11—C60.5 (2)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x+1/2, y1/2, z; (v) x, y+1/2, z+1/2; (vi) x, y1/2, z+1/2; (vii) x, y1, z; (viii) x, y1, z; (ix) x, y+1, z.
(125K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 4800 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.292 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 4800 reflections
a = 26.789 (4) Åθ = 2.9–27.5°
b = 7.173 (1) ŵ = 0.07 mm1
c = 14.246 (2) ÅT = 125 K
V = 2737.5 (7) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1428 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1119 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.046
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.2°
phi and ω scansh = 2833
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 88
Tmin = 0.972, Tmax = 0.998l = 1717
10026 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.101All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.049P)2 + 1.7332P]
where P = (Fo2 + 2Fc2)/3
1428 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C42H28V = 2737.5 (7) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.789 (4) ŵ = 0.07 mm1
b = 7.173 (1) ÅT = 125 K
c = 14.246 (2) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1428 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
1119 reflections with I > 2σ(I)
Tmin = 0.972, Tmax = 0.998Rint = 0.046
10026 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.101All H-atom parameters refined
S = 1.05Δρmax = 0.24 e Å3
1428 reflectionsΔρmin = 0.21 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02723 (7)0.000000.000000.0156 (5)
C20.05315 (5)0.14435 (18)0.04909 (9)0.0160 (4)
C30.02670 (5)0.29541 (18)0.08757 (8)0.0162 (4)
C40.05192 (6)0.44699 (19)0.13405 (9)0.0193 (4)
C50.02634 (6)0.58862 (18)0.17511 (9)0.0213 (4)
C60.10755 (5)0.13436 (18)0.07266 (9)0.0168 (4)
C70.14287 (5)0.2473 (2)0.02915 (10)0.0214 (4)
C80.19178 (6)0.2505 (2)0.05983 (11)0.0265 (5)
C90.20663 (6)0.1387 (2)0.13433 (11)0.0285 (5)
C100.17202 (6)0.0252 (2)0.17824 (11)0.0281 (5)
C110.12299 (6)0.0236 (2)0.14796 (9)0.0218 (4)
H40.0882 (6)0.445 (2)0.1358 (10)0.022 (4)*
H50.0442 (5)0.688 (2)0.2072 (11)0.027 (4)*
H70.1324 (6)0.325 (2)0.0251 (11)0.023 (4)*
H80.2170 (6)0.330 (2)0.0266 (11)0.034 (5)*
H90.2416 (7)0.141 (2)0.1545 (11)0.033 (4)*
H100.1817 (6)0.056 (2)0.2302 (13)0.043 (5)*
H110.0976 (6)0.053 (2)0.1789 (10)0.019 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0217 (10)0.0135 (9)0.0117 (8)0.00000.00000.0017 (7)
C20.0212 (7)0.0145 (6)0.0122 (6)0.0012 (5)0.0017 (5)0.0018 (5)
C30.0235 (7)0.0145 (6)0.0107 (6)0.0014 (5)0.0008 (5)0.0017 (5)
C40.0247 (8)0.0178 (7)0.0155 (6)0.0040 (6)0.0010 (6)0.0005 (5)
C50.0327 (8)0.0149 (6)0.0163 (7)0.0044 (6)0.0005 (6)0.0022 (5)
C60.0196 (7)0.0164 (6)0.0145 (6)0.0003 (5)0.0001 (5)0.0053 (5)
C70.0247 (8)0.0175 (7)0.0219 (7)0.0004 (6)0.0032 (6)0.0011 (6)
C80.0231 (8)0.0240 (8)0.0324 (8)0.0033 (7)0.0055 (6)0.0052 (6)
C90.0191 (8)0.0353 (9)0.0311 (8)0.0013 (7)0.0036 (6)0.0095 (7)
C100.0313 (9)0.0326 (9)0.0205 (7)0.0044 (7)0.0061 (6)0.0009 (6)
C110.0258 (8)0.0221 (7)0.0174 (7)0.0018 (6)0.0010 (6)0.0000 (6)
Geometric parameters (Å, º) top
C1—C21.4295 (16)C7—C81.381 (2)
C1—C2i1.4295 (16)C8—C91.388 (2)
C1—C1ii1.459 (3)C9—C101.383 (2)
C2—C31.4059 (18)C10—C111.383 (2)
C2—C61.4972 (19)C4—H40.972 (16)
C3—C41.4412 (19)C5—H50.973 (15)
C3—C3iii1.4305 (19)C7—H70.993 (15)
C4—C51.358 (2)C8—H81.003 (15)
C5—C5iii1.411 (2)C9—H90.980 (19)
C6—C71.3913 (19)C10—H100.977 (17)
C6—C111.3975 (19)C11—H110.979 (15)
C2···C11i3.582 (2)C8···H8iv2.797 (16)
C4···C73.197 (2)C9···H10vi2.994 (16)
C4···C113.590 (2)C9···H8iv3.081 (16)
C6···C6i2.8286 (19)C11···H7i3.063 (15)
C6···C11i3.3665 (19)H4···C62.458 (14)
C6···C7i3.239 (2)H4···C72.543 (15)
C7···C43.197 (2)H4···H7vii2.57 (2)
C7···C6i3.239 (2)H5···H11viii2.38 (2)
C7···C11i3.229 (2)H5···C3vi3.060 (16)
C8···C8iv3.555 (2)H5···C4vi2.934 (15)
C11···C43.590 (2)H7···C7vii3.081 (14)
C11···C6i3.3665 (19)H7···C11i3.063 (15)
C11···C2i3.582 (2)H7···H4vii2.57 (2)
C11···C7i3.229 (2)H8···H8vii2.55 (2)
C3···H5v3.060 (16)H8···C8iv2.797 (16)
C4···H5v2.934 (15)H8···C9iv3.081 (16)
C4···H11vi2.932 (15)H8···H8iv2.24 (2)
C5···H11vi3.000 (15)H10···C9v2.994 (16)
C6···H42.458 (14)H11···H5ix2.38 (2)
C7···H42.543 (15)H11···C4v2.932 (15)
C7···H7vii3.081 (14)H11···C5v3.000 (15)
C2—C1—C2i121.88 (15)C9—C10—C11120.04 (14)
C1ii—C1—C2119.06 (8)C6—C11—C10121.06 (14)
C1ii—C1—C2i119.06 (8)C3—C4—H4118.0 (9)
C1—C2—C3120.28 (13)C5—C4—H4120.3 (9)
C1—C2—C6123.22 (12)C4—C5—H5120.2 (8)
C3—C2—C6116.10 (11)C5iii—C5—H5119.5 (8)
C2—C3—C4121.62 (12)C6—C7—H7118.8 (9)
C2—C3—C3iii120.26 (12)C8—C7—H7120.3 (9)
C3iii—C3—C4117.96 (12)C7—C8—H8119.9 (9)
C3—C4—C5121.72 (14)C9—C8—H8119.8 (9)
C4—C5—C5iii120.31 (13)C8—C9—H9119.2 (9)
C2—C6—C7122.29 (12)C10—C9—H9121.2 (9)
C2—C6—C11119.17 (12)C9—C10—H10121.0 (9)
C7—C6—C11118.15 (13)C11—C10—H10118.9 (9)
C6—C7—C8120.91 (13)C6—C11—H11117.3 (9)
C7—C8—C9120.27 (14)C10—C11—H11121.6 (9)
C8—C9—C10119.57 (15)
C2i—C1—C2—C3172.80 (10)C2—C3—C3iii—C2iii0.00 (18)
C2i—C1—C2—C614.73 (15)C2—C3—C3iii—C4iii175.49 (11)
C1ii—C1—C2—C37.20 (13)C4—C3—C3iii—C2iii175.49 (11)
C1ii—C1—C2—C6165.28 (9)C4—C3—C3iii—C4iii0.00 (17)
C1—C2—C3—C4177.39 (10)C3—C4—C5—C5iii1.5 (2)
C1—C2—C3—C3iii7.29 (17)C4—C5—C5iii—C4iii0.0 (2)
C6—C2—C3—C49.62 (18)C2—C6—C7—C8172.42 (13)
C6—C2—C3—C3iii165.71 (11)C11—C6—C7—C80.3 (2)
C1—C2—C6—C7109.97 (14)C2—C6—C11—C10173.27 (13)
C1—C2—C6—C1177.38 (16)C7—C6—C11—C100.3 (2)
C3—C2—C6—C777.27 (16)C6—C7—C8—C90.8 (2)
C3—C2—C6—C1195.38 (15)C7—C8—C9—C100.6 (2)
C2—C3—C4—C5176.86 (12)C8—C9—C10—C110.0 (2)
C3iii—C3—C4—C51.43 (18)C9—C10—C11—C60.5 (2)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x+1/2, y1/2, z; (v) x, y+1/2, z+1/2; (vi) x, y1/2, z+1/2; (vii) x, y1, z; (viii) x, y1, z; (ix) x, y+1, z.
(150K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 4648 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.293 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 4648 reflections
a = 26.775 (4) Åθ = 2.9–27.5°
b = 7.168 (1) ŵ = 0.07 mm1
c = 14.258 (2) ÅT = 150 K
V = 2736.4 (7) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1427 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1101 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.045
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.2°
phi and ω scansh = 3328
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 88
Tmin = 0.974, Tmax = 0.998l = 1717
10088 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.105All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.0526P)2 + 1.7289P]
where P = (Fo2 + 2Fc2)/3
1427 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C42H28V = 2736.4 (7) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.775 (4) ŵ = 0.07 mm1
b = 7.168 (1) ÅT = 150 K
c = 14.258 (2) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1427 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
1101 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.998Rint = 0.045
10088 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.105All H-atom parameters refined
S = 1.04Δρmax = 0.25 e Å3
1427 reflectionsΔρmin = 0.18 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02727 (7)0.000000.000000.0172 (5)
C20.05307 (5)0.14417 (18)0.04907 (9)0.0177 (4)
C30.02670 (5)0.29515 (18)0.08757 (8)0.0181 (4)
C40.05186 (6)0.44662 (19)0.13409 (9)0.0220 (4)
C50.02630 (6)0.58805 (19)0.17505 (10)0.0242 (4)
C60.10744 (5)0.13413 (18)0.07267 (9)0.0191 (4)
C70.14283 (5)0.2470 (2)0.02912 (10)0.0242 (4)
C80.19169 (6)0.2498 (2)0.06004 (12)0.0306 (5)
C90.20647 (6)0.1379 (2)0.13425 (11)0.0335 (5)
C100.17191 (6)0.0249 (2)0.17798 (11)0.0324 (5)
C110.12289 (6)0.0237 (2)0.14788 (10)0.0252 (4)
H40.0877 (6)0.448 (2)0.1341 (11)0.023 (4)*
H50.0447 (6)0.688 (2)0.2071 (11)0.031 (4)*
H70.1328 (6)0.324 (2)0.0250 (11)0.031 (4)*
H80.2163 (6)0.330 (2)0.0272 (12)0.038 (5)*
H90.2412 (7)0.142 (2)0.1537 (12)0.043 (5)*
H100.1813 (7)0.055 (3)0.2297 (14)0.048 (5)*
H110.0976 (6)0.053 (2)0.1778 (11)0.026 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0227 (10)0.0165 (9)0.0125 (8)0.00000.00000.0024 (7)
C20.0228 (8)0.0167 (6)0.0136 (6)0.0018 (5)0.0015 (5)0.0016 (5)
C30.0253 (7)0.0171 (7)0.0118 (6)0.0023 (5)0.0008 (5)0.0018 (5)
C40.0270 (9)0.0210 (7)0.0179 (7)0.0047 (6)0.0012 (6)0.0012 (6)
C50.0358 (9)0.0179 (7)0.0190 (7)0.0051 (6)0.0002 (6)0.0035 (5)
C60.0220 (8)0.0190 (7)0.0162 (6)0.0004 (6)0.0004 (5)0.0053 (5)
C70.0268 (8)0.0209 (7)0.0248 (7)0.0006 (6)0.0032 (6)0.0018 (6)
C80.0234 (8)0.0304 (8)0.0379 (9)0.0032 (7)0.0066 (7)0.0065 (7)
C90.0216 (9)0.0428 (9)0.0361 (9)0.0010 (7)0.0048 (7)0.0119 (8)
C100.0332 (9)0.0402 (9)0.0237 (8)0.0050 (8)0.0074 (7)0.0005 (7)
C110.0287 (8)0.0275 (8)0.0194 (7)0.0022 (7)0.0001 (6)0.0007 (6)
Geometric parameters (Å, º) top
C1—C21.4264 (16)C7—C81.381 (2)
C1—C2i1.4264 (16)C8—C91.386 (2)
C1—C1ii1.460 (3)C9—C101.379 (2)
C2—C31.4039 (18)C10—C111.381 (2)
C2—C61.4959 (19)C4—H40.960 (16)
C3—C41.4397 (19)C5—H50.982 (15)
C3—C3iii1.4298 (19)C7—H70.986 (15)
C4—C51.355 (2)C8—H80.992 (16)
C5—C5iii1.408 (2)C9—H90.971 (19)
C6—C71.3921 (19)C10—H100.97 (2)
C6—C111.3956 (19)C11—H110.971 (16)
C2···C11i3.582 (2)C7···H7vii3.087 (14)
C4···C73.197 (2)C8···H8iv2.818 (16)
C4···C113.584 (2)C9···H10vi3.01 (2)
C6···C6i2.8270 (19)C11···H7i3.058 (15)
C6···C11i3.367 (2)H4···C62.472 (15)
C6···C7i3.235 (2)H4···C72.549 (15)
C7···C43.197 (2)H4···H7vii2.56 (2)
C7···C6i3.235 (2)H5···H11viii2.37 (2)
C7···C11i3.228 (2)H5···C3vi3.065 (16)
C8···C8iv3.561 (2)H5···C4vi2.933 (15)
C11···C2i3.582 (2)H7···C7vii3.087 (14)
C11···C43.584 (2)H7···C11i3.058 (15)
C11···C6i3.367 (2)H7···H4vii2.56 (2)
C11···C7i3.228 (2)H8···H8vii2.56 (2)
C3···H5v3.065 (16)H8···C8iv2.818 (16)
C4···H5v2.933 (15)H8···H8iv2.28 (2)
C4···H11vi2.949 (16)H10···C9v3.01 (2)
C5···H11vi3.011 (16)H11···H5ix2.37 (2)
C6···H42.472 (15)H11···C4v2.949 (16)
C7···H42.549 (15)H11···C5v3.011 (16)
C2—C1—C2i122.07 (15)C9—C10—C11120.07 (14)
C1ii—C1—C2118.97 (8)C6—C11—C10121.13 (14)
C1ii—C1—C2i118.97 (8)C3—C4—H4118.4 (9)
C1—C2—C3120.44 (13)C5—C4—H4119.8 (9)
C1—C2—C6123.15 (12)C4—C5—H5119.5 (9)
C3—C2—C6116.01 (11)C5iii—C5—H5120.1 (9)
C2—C3—C4121.75 (12)C6—C7—H7119.3 (9)
C2—C3—C3iii120.19 (12)C8—C7—H7120.0 (9)
C3iii—C3—C4117.90 (12)C7—C8—H8119.2 (10)
C3—C4—C5121.76 (14)C9—C8—H8120.4 (10)
C4—C5—C5iii120.33 (13)C8—C9—H9118.3 (9)
C2—C6—C7122.28 (12)C10—C9—H9122.1 (10)
C2—C6—C11119.25 (12)C9—C10—H10121.2 (11)
C7—C6—C11118.07 (13)C11—C10—H10118.7 (11)
C6—C7—C8120.73 (13)C6—C11—H11116.9 (9)
C7—C8—C9120.40 (14)C10—C11—H11122.0 (9)
C8—C9—C10119.59 (15)
C2i—C1—C2—C3172.78 (10)C2—C3—C3iii—C2iii0.00 (18)
C2i—C1—C2—C614.76 (15)C2—C3—C3iii—C4iii175.47 (11)
C1ii—C1—C2—C37.22 (13)C4—C3—C3iii—C2iii175.47 (11)
C1ii—C1—C2—C6165.25 (9)C4—C3—C3iii—C4iii0.00 (17)
C1—C2—C3—C4177.39 (10)C3—C4—C5—C5iii1.5 (2)
C1—C2—C3—C3iii7.31 (17)C4—C5—C5iii—C4iii0.0 (2)
C6—C2—C3—C49.62 (18)C2—C6—C7—C8172.41 (13)
C6—C2—C3—C3iii165.67 (11)C11—C6—C7—C80.3 (2)
C1—C2—C6—C7109.81 (14)C2—C6—C11—C10173.45 (13)
C1—C2—C6—C1177.54 (16)C7—C6—C11—C100.5 (2)
C3—C2—C6—C777.42 (16)C6—C7—C8—C91.0 (2)
C3—C2—C6—C1195.24 (15)C7—C8—C9—C100.8 (2)
C2—C3—C4—C5176.90 (13)C8—C9—C10—C110.1 (2)
C3iii—C3—C4—C51.50 (19)C9—C10—C11—C60.7 (2)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x+1/2, y1/2, z; (v) x, y+1/2, z+1/2; (vi) x, y1/2, z+1/2; (vii) x, y1, z; (viii) x, y1, z; (ix) x, y+1, z.
(175K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 4431 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.284 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 4431 reflections
a = 26.828 (4) Åθ = 2.9–27.5°
b = 7.181 (1) ŵ = 0.07 mm1
c = 14.306 (2) ÅT = 175 K
V = 2756.1 (7) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1434 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1085 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.046
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.2°
phi and ω scansh = 3328
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 88
Tmin = 0.961, Tmax = 0.998l = 1717
10119 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.100All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0492P)2 + 1.0967P]
where P = (Fo2 + 2Fc2)/3
1434 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C42H28V = 2756.1 (7) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.828 (4) ŵ = 0.07 mm1
b = 7.181 (1) ÅT = 175 K
c = 14.306 (2) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1434 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
1085 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.998Rint = 0.046
10119 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.100All H-atom parameters refined
S = 1.06Δρmax = 0.22 e Å3
1434 reflectionsΔρmin = 0.20 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02718 (7)0.000000.000000.0197 (5)
C20.05303 (5)0.14399 (17)0.04909 (8)0.0206 (4)
C30.02673 (5)0.29472 (17)0.08762 (8)0.0206 (4)
C40.05186 (6)0.44615 (18)0.13392 (9)0.0251 (4)
C50.02622 (6)0.58729 (19)0.17496 (9)0.0282 (4)
C60.10736 (5)0.13391 (18)0.07267 (9)0.0216 (4)
C70.14277 (5)0.24639 (19)0.02938 (10)0.0278 (4)
C80.19159 (6)0.2491 (2)0.06005 (11)0.0353 (5)
C90.20620 (6)0.1376 (2)0.13407 (11)0.0388 (5)
C100.17173 (6)0.0245 (2)0.17770 (11)0.0379 (5)
C110.12281 (6)0.0235 (2)0.14762 (9)0.0290 (5)
H40.0886 (6)0.447 (2)0.1352 (10)0.031 (4)*
H50.0443 (5)0.686 (2)0.2063 (10)0.034 (4)*
H70.1330 (6)0.324 (2)0.0237 (11)0.035 (4)*
H80.2168 (6)0.328 (2)0.0272 (11)0.048 (5)*
H90.2406 (7)0.139 (2)0.1527 (11)0.043 (5)*
H100.1809 (6)0.056 (2)0.2295 (13)0.054 (5)*
H110.0975 (5)0.053 (2)0.1780 (10)0.027 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0248 (10)0.0196 (9)0.0148 (8)0.00000.00000.0019 (7)
C20.0262 (8)0.0201 (6)0.0154 (6)0.0019 (5)0.0016 (5)0.0015 (5)
C30.0285 (7)0.0203 (6)0.0130 (6)0.0015 (5)0.0006 (5)0.0019 (5)
C40.0307 (9)0.0243 (7)0.0204 (7)0.0055 (6)0.0017 (6)0.0012 (5)
C50.0409 (9)0.0214 (7)0.0223 (7)0.0054 (6)0.0001 (6)0.0039 (5)
C60.0236 (8)0.0227 (6)0.0186 (6)0.0009 (5)0.0003 (5)0.0055 (5)
C70.0295 (8)0.0250 (7)0.0288 (7)0.0013 (6)0.0037 (6)0.0013 (6)
C80.0271 (8)0.0364 (8)0.0424 (9)0.0040 (7)0.0070 (7)0.0064 (7)
C90.0230 (9)0.0513 (10)0.0420 (9)0.0006 (7)0.0062 (7)0.0133 (8)
C100.0374 (10)0.0486 (10)0.0278 (8)0.0049 (8)0.0092 (7)0.0002 (7)
C110.0320 (9)0.0340 (8)0.0211 (7)0.0030 (7)0.0000 (6)0.0012 (6)
Geometric parameters (Å, º) top
C1—C21.4294 (15)C7—C81.381 (2)
C1—C2i1.4294 (15)C8—C91.384 (2)
C1—C1ii1.458 (3)C9—C101.380 (2)
C2—C31.4047 (18)C10—C111.381 (2)
C2—C61.4978 (19)C4—H40.986 (16)
C3—C41.4407 (19)C5—H50.969 (14)
C3—C3iii1.4342 (19)C7—H70.978 (15)
C4—C51.358 (2)C8—H81.000 (16)
C5—C5iii1.407 (2)C9—H90.961 (19)
C6—C71.3923 (19)C10—H100.972 (17)
C6—C111.3965 (19)C11—H110.976 (14)
C2···C11i3.5876 (19)C7···H7vii3.097 (14)
C4···C73.200 (2)C8···H8iv2.812 (16)
C4···C113.588 (2)C9···H10vi3.019 (16)
C6···C6i2.8323 (19)C11···H7i3.073 (15)
C6···C11i3.3736 (19)H4···C62.472 (14)
C6···C7i3.239 (2)H4···C72.545 (15)
C7···C43.200 (2)H4···H7vii2.58 (2)
C7···C6i3.239 (2)H5···H11viii2.39 (2)
C7···C11i3.233 (2)H5···C3vi3.086 (14)
C8···C8iv3.574 (2)H5···C4vi2.959 (14)
C11···C2i3.5876 (19)H7···C7vii3.097 (14)
C11···C43.588 (2)H7···C11i3.073 (15)
C11···C6i3.3736 (19)H7···H4vii2.58 (2)
C11···C7i3.233 (2)H8···H8vii2.59 (2)
C3···H5v3.086 (14)H8···C8iv2.812 (16)
C4···H5v2.959 (14)H8···H8iv2.24 (2)
C4···H11vi2.956 (14)H10···C9v3.019 (16)
C5···H11vi3.016 (14)H11···H5ix2.39 (2)
C6···H42.472 (14)H11···C4v2.956 (14)
C7···H42.545 (15)H11···C5v3.016 (14)
C2—C1—C2i121.95 (15)C9—C10—C11119.93 (14)
C1ii—C1—C2119.02 (8)C6—C11—C10121.22 (14)
C1ii—C1—C2i119.02 (8)C3—C4—H4118.8 (8)
C1—C2—C3120.43 (13)C5—C4—H4119.6 (8)
C1—C2—C6123.22 (12)C4—C5—H5119.5 (8)
C3—C2—C6115.95 (11)C5iii—C5—H5120.0 (8)
C2—C3—C4121.80 (12)C6—C7—H7119.6 (9)
C2—C3—C3iii120.15 (11)C8—C7—H7119.5 (9)
C3iii—C3—C4117.90 (12)C7—C8—H8120.0 (9)
C3—C4—C5121.66 (14)C9—C8—H8119.7 (9)
C4—C5—C5iii120.42 (13)C8—C9—H9118.6 (9)
C2—C6—C7122.40 (12)C10—C9—H9121.6 (9)
C2—C6—C11119.29 (12)C9—C10—H10121.7 (9)
C7—C6—C11117.93 (13)C11—C10—H10118.4 (9)
C6—C7—C8120.92 (13)C6—C11—H11117.1 (8)
C7—C8—C9120.22 (14)C10—C11—H11121.7 (8)
C8—C9—C10119.78 (15)
C2i—C1—C2—C3172.78 (10)C2—C3—C3iii—C2iii0.02 (18)
C2i—C1—C2—C614.78 (14)C2—C3—C3iii—C4iii175.64 (11)
C1ii—C1—C2—C37.22 (12)C4—C3—C3iii—C2iii175.64 (11)
C1ii—C1—C2—C6165.22 (8)C4—C3—C3iii—C4iii0.02 (18)
C1—C2—C3—C4177.23 (10)C3—C4—C5—C5iii1.3 (2)
C1—C2—C3—C3iii7.30 (16)C4—C5—C5iii—C4iii0.0 (2)
C6—C2—C3—C49.80 (17)C2—C6—C7—C8172.50 (13)
C6—C2—C3—C3iii165.67 (11)C11—C6—C7—C80.3 (2)
C1—C2—C6—C7109.75 (14)C2—C6—C11—C10173.46 (13)
C1—C2—C6—C1177.54 (15)C7—C6—C11—C100.4 (2)
C3—C2—C6—C777.51 (16)C6—C7—C8—C90.8 (2)
C3—C2—C6—C1195.21 (15)C7—C8—C9—C100.5 (2)
C2—C3—C4—C5176.85 (12)C8—C9—C10—C110.2 (2)
C3iii—C3—C4—C51.28 (18)C9—C10—C11—C60.7 (2)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x+1/2, y1/2, z; (v) x, y+1/2, z+1/2; (vi) x, y1/2, z+1/2; (vii) x, y1, z; (viii) x, y1, z; (ix) x, y+1, z.
(200K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 4251 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.281 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 4251 reflections
a = 26.838 (4) Åθ = 2.8–27.4°
b = 7.181 (1) ŵ = 0.07 mm1
c = 14.332 (2) ÅT = 200 K
V = 2762.1 (7) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1437 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1075 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.045
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.2°
phi and ω scansh = 3328
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 88
Tmin = 0.956, Tmax = 0.996l = 1717
10162 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0595P)2 + 1.3599P]
where P = (Fo2 + 2Fc2)/3
1437 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C42H28V = 2762.1 (7) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.838 (4) ŵ = 0.07 mm1
b = 7.181 (1) ÅT = 200 K
c = 14.332 (2) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1437 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
1075 reflections with I > 2σ(I)
Tmin = 0.956, Tmax = 0.996Rint = 0.045
10162 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.113All H-atom parameters refined
S = 1.03Δρmax = 0.23 e Å3
1437 reflectionsΔρmin = 0.18 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02718 (7)0.000000.000000.0215 (6)
C20.05301 (5)0.14396 (19)0.04907 (9)0.0221 (4)
C30.02666 (5)0.29437 (19)0.08762 (9)0.0224 (4)
C40.05171 (6)0.4456 (2)0.13397 (10)0.0275 (5)
C50.02627 (6)0.5864 (2)0.17497 (10)0.0315 (5)
C60.10730 (5)0.13351 (19)0.07261 (9)0.0236 (4)
C70.14271 (6)0.2461 (2)0.02964 (11)0.0310 (5)
C80.19149 (6)0.2484 (3)0.06023 (13)0.0401 (6)
C90.20606 (7)0.1373 (3)0.13390 (13)0.0442 (6)
C100.17164 (7)0.0244 (3)0.17747 (12)0.0430 (6)
C110.12264 (6)0.0233 (2)0.14730 (10)0.0320 (5)
H40.0880 (7)0.443 (2)0.1341 (12)0.034 (5)*
H50.0447 (6)0.686 (2)0.2055 (12)0.038 (5)*
H70.1325 (6)0.324 (2)0.0239 (11)0.032 (4)*
H80.2169 (7)0.328 (3)0.0280 (13)0.055 (6)*
H90.2407 (8)0.139 (2)0.1536 (12)0.053 (5)*
H100.1809 (8)0.057 (3)0.2298 (16)0.068 (6)*
H110.0971 (6)0.052 (2)0.1789 (12)0.035 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0261 (11)0.0214 (10)0.0169 (9)0.00000.00000.0021 (7)
C20.0268 (8)0.0222 (7)0.0172 (7)0.0029 (6)0.0017 (5)0.0014 (5)
C30.0304 (8)0.0223 (7)0.0146 (6)0.0020 (6)0.0007 (5)0.0020 (5)
C40.0325 (10)0.0262 (7)0.0239 (7)0.0053 (6)0.0022 (7)0.0025 (6)
C50.0441 (9)0.0243 (7)0.0260 (8)0.0064 (7)0.0008 (7)0.0052 (6)
C60.0258 (8)0.0243 (7)0.0208 (7)0.0012 (6)0.0002 (6)0.0065 (5)
C70.0312 (9)0.0285 (8)0.0333 (8)0.0015 (7)0.0049 (7)0.0011 (7)
C80.0286 (9)0.0419 (10)0.0499 (11)0.0046 (8)0.0079 (8)0.0082 (8)
C90.0256 (10)0.0589 (12)0.0482 (11)0.0010 (9)0.0069 (8)0.0147 (9)
C100.0415 (11)0.0562 (11)0.0312 (9)0.0063 (9)0.0103 (8)0.0009 (8)
C110.0335 (9)0.0384 (9)0.0241 (7)0.0026 (7)0.0002 (7)0.0013 (7)
Geometric parameters (Å, º) top
C1—C21.4296 (16)C7—C81.381 (2)
C1—C2i1.4296 (16)C8—C91.380 (3)
C1—C1ii1.459 (3)C9—C101.379 (3)
C2—C31.4043 (19)C10—C111.384 (2)
C2—C61.4975 (19)C4—H40.974 (19)
C3—C41.440 (2)C5—H50.974 (16)
C3—C3iii1.4310 (19)C7—H70.988 (15)
C4—C51.354 (2)C8—H81.00 (2)
C5—C5iii1.410 (2)C9—H90.97 (2)
C6—C71.391 (2)C10—H100.98 (2)
C6—C111.394 (2)C11—H110.984 (16)
C2···C11i3.586 (2)C7···H42.529 (17)
C4···C73.202 (2)C8···H8iv2.819 (19)
C4···C113.586 (2)C9···H10v3.02 (2)
C6···C11i3.372 (2)C11···H7i3.069 (15)
C6···C6i2.8299 (19)H4···C62.446 (15)
C6···C7i3.238 (2)H4···C72.529 (17)
C7···C43.202 (2)H4···H7vii2.59 (2)
C7···C6i3.238 (2)H5···H11viii2.38 (2)
C7···C11i3.235 (2)H5···C4v2.967 (16)
C8···C8iv3.584 (2)H7···C11i3.069 (15)
C11···C6i3.372 (2)H7···H4vii2.59 (2)
C11···C2i3.586 (2)H8···H8vii2.60 (3)
C11···C7i3.235 (2)H8···C8iv2.819 (19)
C11···C43.586 (2)H8···H8iv2.25 (3)
C4···H11v2.946 (17)H10···C9vi3.02 (2)
C4···H5vi2.967 (16)H11···H5ix2.38 (2)
C5···H11v2.998 (17)H11···C4vi2.946 (17)
C6···H42.446 (15)H11···C5vi2.998 (17)
C2—C1—C2i121.99 (15)C9—C10—C11119.90 (17)
C1ii—C1—C2119.01 (9)C6—C11—C10121.16 (15)
C1ii—C1—C2i119.01 (9)C3—C4—H4117.0 (9)
C1—C2—C3120.37 (13)C5—C4—H4121.2 (9)
C1—C2—C6123.12 (12)C4—C5—H5119.2 (9)
C3—C2—C6116.10 (12)C5iii—C5—H5120.5 (9)
C2—C3—C4121.77 (13)C6—C7—H7118.9 (9)
C2—C3—C3iii120.24 (12)C8—C7—H7120.2 (9)
C3iii—C3—C4117.84 (12)C7—C8—H8120.4 (11)
C3—C4—C5121.87 (14)C9—C8—H8119.3 (11)
C4—C5—C5iii120.28 (14)C8—C9—H9119.1 (10)
C2—C6—C7122.39 (12)C10—C9—H9121.1 (10)
C2—C6—C11119.28 (12)C9—C10—H10121.7 (13)
C7—C6—C11117.92 (13)C11—C10—H10118.4 (13)
C6—C7—C8120.93 (15)C6—C11—H11117.4 (10)
C7—C8—C9120.31 (17)C10—C11—H11121.4 (10)
C8—C9—C10119.78 (17)
C2i—C1—C2—C3172.85 (11)C2—C3—C3iii—C2iii0.00 (19)
C2i—C1—C2—C614.84 (15)C2—C3—C3iii—C4iii175.64 (12)
C1ii—C1—C2—C37.15 (14)C4—C3—C3iii—C2iii175.64 (12)
C1ii—C1—C2—C6165.16 (9)C4—C3—C3iii—C4iii0.00 (19)
C1—C2—C3—C4177.30 (11)C3—C4—C5—C5iii1.3 (2)
C1—C2—C3—C3iii7.23 (18)C4—C5—C5iii—C4iii0.0 (2)
C6—C2—C3—C49.87 (19)C2—C6—C7—C8172.52 (15)
C6—C2—C3—C3iii165.60 (12)C11—C6—C7—C80.1 (2)
C1—C2—C6—C7109.92 (15)C2—C6—C11—C10173.32 (15)
C1—C2—C6—C1177.61 (16)C7—C6—C11—C100.5 (2)
C3—C2—C6—C777.47 (17)C6—C7—C8—C90.5 (3)
C3—C2—C6—C1195.00 (16)C7—C8—C9—C100.4 (3)
C2—C3—C4—C5176.88 (13)C8—C9—C10—C110.2 (3)
C3iii—C3—C4—C51.3 (2)C9—C10—C11—C60.6 (3)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x+1/2, y1/2, z; (v) x, y1/2, z+1/2; (vi) x, y+1/2, z+1/2; (vii) x, y1, z; (viii) x, y1, z; (ix) x, y+1, z.
(235K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 3849 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.282 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 3849 reflections
a = 26.818 (5) Åθ = 2.8–27.4°
b = 7.174 (1) ŵ = 0.07 mm1
c = 14.348 (3) ÅT = 235 K
V = 2760.5 (9) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1437 independent reflections
Radiation source: fine focus sealed Siemens Mo tube997 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.052
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.0°
phi and ω scansh = 3333
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 88
Tmin = 0.952, Tmax = 0.992l = 1617
10021 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: difference Fourier map
wR(F2) = 0.109All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0433P)2 + 2.1676P]
where P = (Fo2 + 2Fc2)/3
1437 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C42H28V = 2760.5 (9) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.818 (5) ŵ = 0.07 mm1
b = 7.174 (1) ÅT = 235 K
c = 14.348 (3) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1437 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
997 reflections with I > 2σ(I)
Tmin = 0.952, Tmax = 0.992Rint = 0.052
10021 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.109All H-atom parameters refined
S = 1.03Δρmax = 0.24 e Å3
1437 reflectionsΔρmin = 0.19 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02725 (7)0.000000.000000.0237 (7)
C20.05282 (5)0.1437 (2)0.04905 (11)0.0246 (5)
C30.02673 (5)0.2940 (2)0.08752 (10)0.0247 (5)
C40.05163 (6)0.4448 (2)0.13381 (12)0.0311 (5)
C50.02624 (7)0.5852 (2)0.17462 (12)0.0355 (6)
C60.10725 (6)0.1332 (2)0.07259 (11)0.0265 (5)
C70.14260 (6)0.2455 (3)0.02974 (13)0.0342 (6)
C80.19131 (6)0.2471 (3)0.06057 (15)0.0459 (7)
C90.20583 (7)0.1364 (3)0.13366 (15)0.0505 (7)
C100.17143 (7)0.0242 (3)0.17699 (14)0.0497 (7)
C110.12234 (7)0.0230 (3)0.14690 (12)0.0364 (6)
H40.0880 (6)0.443 (2)0.1359 (12)0.033 (5)*
H50.0443 (6)0.682 (3)0.2055 (12)0.042 (5)*
H70.1326 (6)0.324 (2)0.0238 (12)0.032 (5)*
H80.2163 (7)0.325 (3)0.0277 (13)0.055 (6)*
H90.2410 (8)0.137 (3)0.1527 (13)0.060 (6)*
H100.1796 (7)0.052 (3)0.2290 (15)0.060 (6)*
H110.0971 (7)0.054 (3)0.1768 (13)0.041 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0276 (11)0.0238 (12)0.0198 (11)0.00000.00000.0019 (9)
C20.0285 (8)0.0245 (8)0.0207 (8)0.0034 (7)0.0011 (6)0.0014 (7)
C30.0322 (8)0.0234 (8)0.0185 (8)0.0016 (7)0.0015 (6)0.0018 (6)
C40.0349 (9)0.0286 (9)0.0297 (9)0.0060 (7)0.0020 (7)0.0032 (8)
C50.0483 (10)0.0258 (9)0.0323 (10)0.0064 (8)0.0013 (8)0.0070 (8)
C60.0278 (8)0.0276 (9)0.0241 (8)0.0013 (7)0.0002 (6)0.0059 (7)
C70.0319 (9)0.0312 (10)0.0395 (11)0.0022 (8)0.0055 (8)0.0008 (8)
C80.0302 (9)0.0481 (12)0.0595 (14)0.0061 (9)0.0090 (9)0.0093 (11)
C90.0276 (10)0.0661 (14)0.0579 (14)0.0019 (10)0.0065 (9)0.0168 (12)
C100.0466 (11)0.0660 (15)0.0364 (11)0.0077 (11)0.0132 (9)0.0001 (11)
C110.0367 (9)0.0429 (11)0.0296 (9)0.0027 (8)0.0011 (8)0.0012 (8)
Geometric parameters (Å, º) top
C1—C21.4242 (17)C7—C81.379 (2)
C1—C2i1.4242 (17)C8—C91.372 (3)
C1—C1ii1.462 (3)C9—C101.373 (3)
C2—C31.399 (2)C10—C111.386 (3)
C2—C61.500 (2)C4—H40.976 (16)
C3—C41.434 (2)C5—H50.956 (19)
C3—C3iii1.4337 (19)C7—H70.990 (16)
C4—C51.349 (2)C8—H80.99 (2)
C5—C5iii1.407 (3)C9—H90.98 (2)
C6—C71.388 (2)C10—H100.95 (2)
C6—C111.388 (2)C11—H110.97 (2)
C2···C11i3.579 (2)C6···H42.456 (15)
C4···C73.198 (2)C7···H42.544 (16)
C4···C113.576 (3)C8···H8iv2.830 (19)
C6···C11i3.367 (2)C9···H10v3.06 (2)
C6···C6i2.827 (2)C11···H7i3.065 (16)
C6···C7i3.230 (3)H4···C62.456 (15)
C7···C43.198 (2)H4···C72.544 (16)
C7···C6i3.230 (3)H5···H11vii2.40 (3)
C7···C11i3.229 (3)H5···C4v2.985 (19)
C8···C8iv3.596 (3)H7···C11i3.065 (16)
C11···C6i3.367 (2)H8···C8iv2.830 (19)
C11···C2i3.579 (2)H8···H8iv2.25 (3)
C11···C7i3.229 (3)H10···C9vi3.06 (2)
C11···C43.576 (3)H11···H5viii2.40 (3)
C4···H11v2.978 (19)H11···C4vi2.978 (19)
C4···H5vi2.985 (19)H11···C5vi3.025 (19)
C5···H11v3.025 (19)
C2—C1—C2i122.43 (15)C9—C10—C11120.06 (19)
C1ii—C1—C2118.78 (9)C6—C11—C10120.86 (18)
C1ii—C1—C2i118.78 (9)C3—C4—H4118.0 (9)
C1—C2—C3120.80 (13)C5—C4—H4120.1 (9)
C1—C2—C6122.92 (13)C4—C5—H5119.2 (11)
C3—C2—C6115.88 (13)C5iii—C5—H5120.5 (10)
C2—C3—C4122.09 (13)C6—C7—H7119.3 (9)
C2—C3—C3iii120.01 (13)C8—C7—H7120.1 (9)
C3iii—C3—C4117.75 (13)C7—C8—H8119.5 (11)
C3—C4—C5121.94 (15)C9—C8—H8119.9 (11)
C4—C5—C5iii120.30 (15)C8—C9—H9118.9 (12)
C2—C6—C7122.40 (14)C10—C9—H9121.5 (12)
C2—C6—C11119.04 (14)C9—C10—H10122.5 (12)
C7—C6—C11118.16 (16)C11—C10—H10117.4 (12)
C6—C7—C8120.65 (18)C6—C11—H11117.3 (11)
C7—C8—C9120.61 (18)C10—C11—H11121.8 (11)
C8—C9—C10119.65 (17)
C2i—C1—C2—C3172.73 (12)C2—C3—C3iii—C2iii0.0 (2)
C2i—C1—C2—C614.79 (18)C2—C3—C3iii—C4iii175.56 (14)
C1ii—C1—C2—C37.27 (16)C4—C3—C3iii—C2iii175.56 (14)
C1ii—C1—C2—C6165.21 (11)C4—C3—C3iii—C4iii0.0 (2)
C1—C2—C3—C4177.28 (13)C3—C4—C5—C5iii1.4 (3)
C1—C2—C3—C3iii7.4 (2)C4—C5—C5iii—C4iii0.0 (3)
C6—C2—C3—C49.7 (2)C2—C6—C7—C8172.54 (17)
C6—C2—C3—C3iii165.63 (13)C11—C6—C7—C80.1 (3)
C1—C2—C6—C7109.71 (18)C2—C6—C11—C10173.33 (17)
C1—C2—C6—C1177.7 (2)C7—C6—C11—C100.5 (3)
C3—C2—C6—C777.5 (2)C6—C7—C8—C90.6 (3)
C3—C2—C6—C1195.10 (18)C7—C8—C9—C100.6 (3)
C2—C3—C4—C5176.86 (15)C8—C9—C10—C110.0 (3)
C3iii—C3—C4—C51.4 (2)C9—C10—C11—C60.5 (3)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x+1/2, y1/2, z; (v) x, y1/2, z+1/2; (vi) x, y+1/2, z+1/2; (vii) x, y1, z; (viii) x, y+1, z.
(275K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 3697 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.259 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 3697 reflections
a = 26.938 (5) Åθ = 2.8–27.2°
b = 7.211 (1) ŵ = 0.07 mm1
c = 14.461 (3) ÅT = 275 K
V = 2809.1 (9) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1466 independent reflections
Radiation source: fine focus sealed Siemens Mo tube1036 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.050
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.2°
phi and ω scansh = 3328
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 99
Tmin = 0.948, Tmax = 0.996l = 1818
10370 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125All H-atom parameters refined
S = 1.05 w = 1/[σ2(Fo2) + (0.0656P)2 + 0.4032P]
where P = (Fo2 + 2Fc2)/3
1466 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C42H28V = 2809.1 (9) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.938 (5) ŵ = 0.07 mm1
b = 7.211 (1) ÅT = 275 K
c = 14.461 (3) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1466 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
1036 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.996Rint = 0.050
10370 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.125All H-atom parameters refined
S = 1.05Δρmax = 0.17 e Å3
1466 reflectionsΔρmin = 0.16 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02714 (7)0.000000.000000.0294 (6)
C20.05290 (5)0.14318 (18)0.04901 (9)0.0301 (4)
C30.02661 (5)0.29299 (18)0.08757 (9)0.0310 (4)
C40.05169 (7)0.4439 (2)0.13369 (10)0.0387 (5)
C50.02612 (7)0.5841 (2)0.17468 (11)0.0433 (5)
C60.10704 (6)0.13275 (19)0.07255 (10)0.0329 (4)
C70.14248 (6)0.2446 (2)0.03009 (12)0.0425 (6)
C80.19109 (7)0.2464 (3)0.06060 (15)0.0560 (7)
C90.20544 (8)0.1361 (3)0.13363 (15)0.0626 (8)
C100.17115 (8)0.0238 (3)0.17662 (14)0.0599 (7)
C110.12231 (7)0.0226 (2)0.14648 (11)0.0449 (6)
H40.0890 (7)0.441 (2)0.1366 (12)0.053 (5)*
H50.0450 (6)0.684 (2)0.2061 (12)0.053 (5)*
H70.1322 (6)0.324 (2)0.0219 (12)0.048 (5)*
H80.2160 (7)0.324 (3)0.0268 (14)0.078 (6)*
H90.2404 (9)0.138 (3)0.1536 (15)0.083 (7)*
H100.1794 (8)0.057 (3)0.2296 (16)0.085 (7)*
H110.0964 (7)0.050 (2)0.1780 (13)0.054 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0327 (11)0.0304 (10)0.0251 (9)0.00000.00000.0019 (8)
C20.0346 (9)0.0310 (7)0.0248 (7)0.0035 (6)0.0017 (6)0.0013 (6)
C30.0402 (8)0.0297 (7)0.0230 (7)0.0023 (6)0.0009 (6)0.0012 (5)
C40.0454 (11)0.0365 (8)0.0343 (8)0.0069 (7)0.0020 (7)0.0043 (7)
C50.0584 (11)0.0337 (8)0.0379 (9)0.0075 (7)0.0014 (8)0.0080 (7)
C60.0340 (9)0.0351 (7)0.0295 (7)0.0033 (6)0.0003 (6)0.0063 (6)
C70.0391 (10)0.0411 (9)0.0473 (10)0.0035 (8)0.0062 (8)0.0020 (8)
C80.0383 (11)0.0596 (11)0.0700 (13)0.0077 (9)0.0104 (9)0.0108 (10)
C90.0377 (12)0.0814 (14)0.0687 (14)0.0016 (10)0.0074 (10)0.0196 (12)
C100.0566 (13)0.0780 (13)0.0452 (11)0.0076 (11)0.0159 (9)0.0001 (10)
C110.0442 (11)0.0551 (10)0.0354 (9)0.0028 (8)0.0015 (8)0.0026 (8)
Geometric parameters (Å, º) top
C1—C21.4317 (16)C7—C81.382 (3)
C1—C2i1.4317 (16)C8—C91.378 (3)
C1—C1ii1.462 (3)C9—C101.377 (3)
C2—C31.4069 (19)C10—C111.386 (3)
C2—C61.500 (2)C4—H41.006 (19)
C3—C41.444 (2)C5—H50.992 (16)
C3—C3iii1.4336 (19)C7—H70.985 (16)
C4—C51.359 (2)C8—H81.00 (2)
C5—C5iii1.407 (3)C9—H90.99 (2)
C6—C71.393 (2)C10—H100.99 (2)
C6—C111.394 (2)C11—H110.984 (18)
C2···C11i3.594 (2)C6···H42.457 (15)
C4···C73.208 (2)C7···H42.540 (17)
C4···C113.589 (2)C8···H8vi2.849 (19)
C6···C11i3.385 (2)C9···H10iv3.05 (2)
C6···C6i2.841 (2)C11···H7i3.092 (16)
C6···C7i3.243 (2)H4···C62.457 (15)
C7···C43.208 (2)H4···C72.540 (17)
C7···C6i3.243 (2)H5···H11vii2.40 (2)
C7···C11i3.245 (2)H5···C4iv2.985 (16)
C11···C7i3.245 (2)H7···C11i3.092 (16)
C11···C6i3.385 (2)H8···C8vi2.849 (19)
C11···C2i3.594 (2)H8···H8vi2.26 (3)
C11···C43.589 (2)H10···C9v3.05 (2)
C4···H11iv2.978 (19)H11···H5viii2.40 (2)
C4···H5v2.985 (16)H11···C4v2.978 (19)
C5···H11iv3.010 (19)H11···C5v3.010 (19)
C2—C1—C2i122.02 (15)C9—C10—C11119.90 (19)
C1ii—C1—C2118.99 (8)C6—C11—C10121.18 (16)
C1ii—C1—C2i118.99 (8)C3—C4—H4118.1 (9)
C1—C2—C3120.39 (13)C5—C4—H4120.2 (9)
C1—C2—C6123.20 (12)C4—C5—H5118.7 (9)
C3—C2—C6115.98 (12)C5iii—C5—H5120.8 (9)
C2—C3—C4121.75 (13)C6—C7—H7118.7 (9)
C2—C3—C3iii120.22 (12)C8—C7—H7120.3 (9)
C3iii—C3—C4117.89 (13)C7—C8—H8119.0 (11)
C3—C4—C5121.65 (16)C9—C8—H8120.6 (11)
C4—C5—C5iii120.45 (15)C8—C9—H9119.0 (13)
C2—C6—C7122.53 (13)C10—C9—H9121.1 (13)
C2—C6—C11119.32 (14)C9—C10—H10123.1 (13)
C7—C6—C11117.77 (15)C11—C10—H10117.0 (13)
C6—C7—C8120.95 (16)C6—C11—H11116.7 (11)
C7—C8—C9120.35 (18)C10—C11—H11122.1 (11)
C8—C9—C10119.8 (2)
C2i—C1—C2—C3172.82 (11)C2—C3—C3iii—C2iii0.00 (19)
C2i—C1—C2—C614.93 (15)C2—C3—C3iii—C4iii175.80 (12)
C1ii—C1—C2—C37.18 (14)C4—C3—C3iii—C2iii175.80 (12)
C1ii—C1—C2—C6165.07 (9)C4—C3—C3iii—C4iii0.00 (19)
C1—C2—C3—C4177.10 (11)C3—C4—C5—C5iii1.2 (2)
C1—C2—C3—C3iii7.27 (18)C4—C5—C5iii—C4iii0.0 (2)
C6—C2—C3—C410.11 (19)C2—C6—C7—C8172.64 (16)
C6—C2—C3—C3iii165.52 (12)C11—C6—C7—C80.2 (2)
C1—C2—C6—C7109.65 (15)C2—C6—C11—C10173.26 (15)
C1—C2—C6—C1177.62 (17)C7—C6—C11—C100.2 (2)
C3—C2—C6—C777.78 (18)C6—C7—C8—C90.4 (3)
C3—C2—C6—C1194.94 (16)C7—C8—C9—C100.2 (3)
C2—C3—C4—C5176.86 (14)C8—C9—C10—C110.2 (3)
C3iii—C3—C4—C51.1 (2)C9—C10—C11—C60.4 (3)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x, y1/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x+1/2, y1/2, z; (vii) x, y1, z; (viii) x, y+1, z.
(293K) top
Crystal data top
C42H28The final unit cell was obtained from the xyz centroids of 1924 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68Dx = 1.269 Mg m3
Orthorhombic, CmcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2Cell parameters from 1924 reflections
a = 26.86 (1) Åθ = 2.8–23.4°
b = 7.193 (3) ŵ = 0.07 mm1
c = 14.433 (5) ÅT = 293 K
V = 2788.5 (18) Å3Platelet, orange
Z = 40.51 × 0.45 × 0.03 mm
F(000) = 1120
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1451 independent reflections
Radiation source: fine focus sealed Siemens Mo tube938 reflections with I > 2σ(I)
Parallel mounted graphite monochromatorRint = 0.061
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm-1θmax = 26.4°, θmin = 3.0°
phi and ω scansh = 3333
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
k = 88
Tmin = 0.949, Tmax = 0.998l = 1818
10259 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: structure-invariant direct methods
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.123All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.070P)2 + 0.P]
where P = (Fo2 + 2Fc2)/3
1451 reflections(Δ/σ)max < 0.001
124 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.17 e Å3
Crystal data top
C42H28V = 2788.5 (18) Å3
Mr = 532.68Z = 4
Orthorhombic, CmcaMo Kα radiation
a = 26.86 (1) ŵ = 0.07 mm1
b = 7.193 (3) ÅT = 293 K
c = 14.433 (5) Å0.51 × 0.45 × 0.03 mm
Data collection top
Bruker Smart Apex; CCD area detector
diffractometer
1451 independent reflections
Absorption correction: multi-scan
(SADABS, Sheldrick, Bruker, 2000))
938 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.998Rint = 0.061
10259 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.123All H-atom parameters refined
S = 1.03Δρmax = 0.15 e Å3
1451 reflectionsΔρmin = 0.17 e Å3
124 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
C10.02705 (7)0.000000.000000.0327 (7)
C20.05294 (5)0.1429 (2)0.04897 (10)0.0335 (5)
C30.02658 (5)0.2928 (2)0.08756 (10)0.0341 (5)
C40.05147 (7)0.4433 (2)0.13347 (11)0.0424 (6)
C50.02589 (7)0.5831 (2)0.17451 (12)0.0475 (6)
C60.10704 (6)0.1325 (2)0.07249 (11)0.0369 (5)
C70.14252 (6)0.2440 (2)0.03033 (13)0.0467 (6)
C80.19095 (7)0.2455 (3)0.06085 (16)0.0623 (8)
C90.20534 (8)0.1351 (3)0.13354 (16)0.0694 (9)
C100.17085 (8)0.0241 (3)0.17627 (15)0.0659 (8)
C110.12213 (7)0.0226 (3)0.14638 (12)0.0499 (6)
H40.0875 (6)0.441 (2)0.1339 (10)0.036 (4)*
H50.0444 (5)0.680 (2)0.2050 (12)0.055 (5)*
H70.1318 (6)0.324 (2)0.0213 (12)0.053 (5)*
H80.2165 (7)0.321 (3)0.0286 (14)0.085 (7)*
H90.2409 (8)0.133 (2)0.1504 (12)0.072 (6)*
H100.1794 (8)0.060 (3)0.2267 (16)0.091 (7)*
H110.0955 (6)0.055 (2)0.1763 (12)0.054 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0352 (12)0.0333 (12)0.0296 (11)0.00000.00000.0037 (9)
C20.0370 (9)0.0335 (8)0.0301 (8)0.0014 (7)0.0015 (6)0.0007 (6)
C30.0428 (9)0.0339 (8)0.0255 (8)0.0042 (7)0.0001 (6)0.0018 (6)
C40.0467 (11)0.0419 (9)0.0386 (9)0.0070 (8)0.0032 (8)0.0046 (8)
C50.0620 (12)0.0373 (10)0.0432 (10)0.0084 (8)0.0022 (8)0.0094 (8)
C60.0369 (9)0.0400 (9)0.0337 (8)0.0032 (7)0.0004 (7)0.0054 (7)
C70.0420 (10)0.0451 (10)0.0531 (11)0.0040 (9)0.0070 (8)0.0034 (9)
C80.0397 (11)0.0683 (14)0.0789 (15)0.0072 (10)0.0104 (10)0.0130 (11)
C90.0391 (12)0.0929 (17)0.0763 (16)0.0026 (12)0.0072 (11)0.0209 (14)
C100.0589 (14)0.0874 (16)0.0515 (12)0.0082 (12)0.0154 (10)0.0006 (11)
C110.0484 (11)0.0611 (12)0.0403 (9)0.0032 (9)0.0019 (8)0.0030 (9)
Geometric parameters (Å, º) top
C1—C21.4282 (18)C7—C81.373 (3)
C1—C2i1.4282 (18)C8—C91.371 (3)
C1—C1ii1.453 (3)C9—C101.370 (3)
C2—C31.405 (2)C10—C111.378 (3)
C2—C61.494 (2)C4—H40.968 (16)
C3—C41.435 (2)C5—H50.963 (15)
C3—C3iii1.428 (2)C7—H70.985 (16)
C4—C51.354 (2)C8—H80.99 (2)
C5—C5iii1.391 (3)C9—H90.99 (2)
C6—C71.386 (2)C10—H100.97 (2)
C6—C111.388 (3)C11—H111.005 (16)
C2···C11i3.581 (3)C6···H42.447 (15)
C4···C73.202 (3)C7···H42.535 (15)
C4···C113.577 (3)C8···H8vi2.842 (19)
C6···C11i3.375 (3)C9···H10iv3.06 (2)
C6···C6i2.831 (2)C11···H7i3.089 (16)
C6···C7i3.232 (3)H4···C62.447 (15)
C7···C43.202 (3)H4···C72.535 (15)
C7···C6i3.232 (3)H5···H11vii2.39 (2)
C7···C11i3.238 (3)H5···C4iv3.010 (16)
C11···C7i3.238 (3)H7···C11i3.089 (16)
C11···C6i3.375 (3)H8···C8vi2.842 (19)
C11···C2i3.581 (3)H8···H8vi2.23 (3)
C11···C43.577 (3)H10···C9v3.06 (2)
C4···H11iv2.990 (17)H11···H5viii2.39 (2)
C4···H5v3.010 (16)H11···C4v2.990 (17)
C5···H11iv3.020 (17)H11···C5v3.020 (17)
C2—C1—C2i121.72 (15)C9—C10—C11120.4 (2)
C1ii—C1—C2119.14 (9)C6—C11—C10120.89 (18)
C1ii—C1—C2i119.14 (9)C3—C4—H4117.1 (9)
C1—C2—C3120.21 (13)C5—C4—H4121.1 (9)
C1—C2—C6123.37 (13)C4—C5—H5118.4 (8)
C3—C2—C6116.01 (12)C5iii—C5—H5121.1 (8)
C2—C3—C4121.83 (13)C6—C7—H7118.0 (9)
C2—C3—C3iii120.26 (13)C8—C7—H7121.0 (9)
C3iii—C3—C4117.78 (13)C7—C8—H8120.6 (12)
C3—C4—C5121.73 (16)C9—C8—H8118.8 (12)
C4—C5—C5iii120.49 (15)C8—C9—H9118.1 (10)
C2—C6—C7122.68 (14)C10—C9—H9122.4 (10)
C2—C6—C11119.15 (14)C9—C10—H10122.6 (13)
C7—C6—C11117.78 (16)C11—C10—H10116.9 (13)
C6—C7—C8120.99 (17)C6—C11—H11116.0 (10)
C7—C8—C9120.52 (19)C10—C11—H11123.1 (10)
C8—C9—C10119.4 (2)
C2i—C1—C2—C3172.81 (12)C2—C3—C3iii—C2iii0.0 (2)
C2i—C1—C2—C614.96 (17)C2—C3—C3iii—C4iii175.85 (14)
C1ii—C1—C2—C37.19 (15)C4—C3—C3iii—C2iii175.85 (14)
C1ii—C1—C2—C6165.04 (10)C4—C3—C3iii—C4iii0.0 (2)
C1—C2—C3—C4177.05 (12)C3—C4—C5—C5iii1.0 (2)
C1—C2—C3—C3iii7.3 (2)C4—C5—C5iii—C4iii0.0 (3)
C6—C2—C3—C410.2 (2)C2—C6—C7—C8172.64 (16)
C6—C2—C3—C3iii165.51 (13)C11—C6—C7—C80.1 (3)
C1—C2—C6—C7109.70 (17)C2—C6—C11—C10173.27 (17)
C1—C2—C6—C1177.70 (19)C7—C6—C11—C100.3 (3)
C3—C2—C6—C777.77 (19)C6—C7—C8—C90.5 (3)
C3—C2—C6—C1194.83 (18)C7—C8—C9—C100.6 (3)
C2—C3—C4—C5176.76 (15)C8—C9—C10—C110.2 (3)
C3iii—C3—C4—C51.0 (2)C9—C10—C11—C60.2 (3)
Symmetry codes: (i) x, y, z; (ii) x, y, z; (iii) x, y, z; (iv) x, y1/2, z+1/2; (v) x, y+1/2, z+1/2; (vi) x+1/2, y1/2, z; (vii) x, y1, z; (viii) x, y+1, z.

Experimental details

(100K)(125K)(150K)(175K)
Crystal data
Chemical formulaC42H28C42H28C42H28C42H28
Mr532.68532.68532.68532.68
Crystal system, space groupOrthorhombic, CmcaOrthorhombic, CmcaOrthorhombic, CmcaOrthorhombic, Cmca
Temperature (K)100125150175
a, b, c (Å)26.789 (4), 7.170 (1), 14.211 (2)26.789 (4), 7.173 (1), 14.246 (2)26.775 (4), 7.168 (1), 14.258 (2)26.828 (4), 7.181 (1), 14.306 (2)
α, β, γ (°)90, 90, 9090, 90, 9090, 90, 9090, 90, 90
V3)2729.6 (7)2737.5 (7)2736.4 (7)2756.1 (7)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.070.070.070.07
Crystal size (mm)0.51 × 0.45 × 0.030.51 × 0.45 × 0.030.51 × 0.45 × 0.030.51 × 0.45 × 0.03
Data collection
DiffractometerBruker Smart Apex; CCD area detector
diffractometer
Bruker Smart Apex; CCD area detector
diffractometer
Bruker Smart Apex; CCD area detector
diffractometer
Bruker Smart Apex; CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS, Sheldrick, Bruker, 2000))
Multi-scan
(SADABS, Sheldrick, Bruker, 2000))
Multi-scan
(SADABS, Sheldrick, Bruker, 2000))
Multi-scan
(SADABS, Sheldrick, Bruker, 2000))
Tmin, Tmax0.952, 0.9980.972, 0.9980.974, 0.9980.961, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
10125, 1424, 1201 10026, 1428, 1119 10088, 1427, 1101 10119, 1434, 1085
Rint0.0350.0460.0450.046
(sin θ/λ)max1)0.6250.6250.6250.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.099, 1.06 0.038, 0.101, 1.05 0.039, 0.105, 1.04 0.039, 0.100, 1.06
No. of reflections1424142814271434
No. of parameters124124124124
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.26, 0.210.24, 0.210.25, 0.180.22, 0.20


(200K)(235K)(275K)(293K)
Crystal data
Chemical formulaC42H28C42H28C42H28C42H28
Mr532.68532.68532.68532.68
Crystal system, space groupOrthorhombic, CmcaOrthorhombic, CmcaOrthorhombic, CmcaOrthorhombic, Cmca
Temperature (K)200235275293
a, b, c (Å)26.838 (4), 7.181 (1), 14.332 (2)26.818 (5), 7.174 (1), 14.348 (3)26.938 (5), 7.211 (1), 14.461 (3)26.86 (1), 7.193 (3), 14.433 (5)
α, β, γ (°)90, 90, 9090, 90, 9090, 90, 9090, 90, 90
V3)2762.1 (7)2760.5 (9)2809.1 (9)2788.5 (18)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.070.070.070.07
Crystal size (mm)0.51 × 0.45 × 0.030.51 × 0.45 × 0.030.51 × 0.45 × 0.030.51 × 0.45 × 0.03
Data collection
DiffractometerBruker Smart Apex; CCD area detector
diffractometer
Bruker Smart Apex; CCD area detector
diffractometer
Bruker Smart Apex; CCD area detector
diffractometer
Bruker Smart Apex; CCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS, Sheldrick, Bruker, 2000))
Multi-scan
(SADABS, Sheldrick, Bruker, 2000))
Multi-scan
(SADABS, Sheldrick, Bruker, 2000))
Multi-scan
(SADABS, Sheldrick, Bruker, 2000))
Tmin, Tmax0.956, 0.9960.952, 0.9920.948, 0.9960.949, 0.998
No. of measured, independent and
observed [I > 2σ(I)] reflections
10162, 1437, 1075 10021, 1437, 997 10370, 1466, 1036 10259, 1451, 938
Rint0.0450.0520.0500.061
(sin θ/λ)max1)0.6250.6250.6250.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.113, 1.03 0.041, 0.109, 1.03 0.042, 0.125, 1.05 0.044, 0.123, 1.03
No. of reflections1437143714661451
No. of parameters124124124124
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.23, 0.180.24, 0.190.17, 0.160.15, 0.17

Computer programs: SMART, Bruker Version 5.624, 2001, SAINT, Bruker Version 6.02A, 2000, XPREP, Bruker Version 5.1/NT, 2000, SHELXS97 (Sheldrick, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLUTO (Meetsma, 2004) PLATON (Spek, 2003), PLATON (Spek, 2003).

 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds