Low-temperature structure of rubrene single crystals grown by vapor transport

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.

Computing details

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

(100K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 4621 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.296 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 4621 reflections
a = 26.789 (4) Å	θ = 2.9–29.3°
b = 7.170 (1) Å	µ = 0.07 mm^−1
c = 14.211 (2) Å	T = 100 K
V = 2729.6 (7) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1424 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1201 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.035
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.0°
phi and ω scans	h = −31→33
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −8→8
Tmin = 0.952, Tmax = 0.998	l = −17→17
10125 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: difference Fourier map
wR(F^2) = 0.099	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0473P)^2 + 2.3678P] where P = (Fo^2 + 2Fc^2)/3
1424 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02737 (6)	0.00000	0.00000	0.0135 (5)
C2	0.05314 (5)	−0.14464 (16)	0.04914 (8)	0.0141 (3)
C3	0.02678 (5)	−0.29578 (16)	0.08755 (8)	0.0142 (4)
C4	0.05191 (5)	−0.44754 (17)	0.13412 (9)	0.0170 (4)
C5	0.02646 (5)	−0.58934 (17)	0.17534 (9)	0.0186 (4)
C6	0.10760 (5)	−0.13448 (16)	0.07274 (8)	0.0148 (3)
C7	0.14292 (5)	−0.24817 (18)	0.02881 (9)	0.0185 (4)
C8	0.19199 (5)	−0.25089 (19)	0.05979 (10)	0.0225 (4)
C9	0.20685 (5)	−0.1389 (2)	0.13448 (10)	0.0244 (4)
C10	0.17219 (5)	−0.0251 (2)	0.17857 (10)	0.0233 (4)
C11	0.12302 (5)	−0.02362 (18)	0.14816 (9)	0.0189 (4)
H4	0.0883 (5)	−0.447 (2)	0.1357 (10)	0.016 (4)*
H5	0.0438 (5)	−0.689 (2)	0.2065 (10)	0.020 (4)*
H7	0.1328 (5)	−0.327 (2)	−0.0256 (10)	0.021 (4)*
H8	0.2167 (5)	−0.332 (2)	0.0279 (11)	0.028 (4)*
H9	0.2413 (6)	−0.140 (2)	0.1546 (10)	0.025 (4)*
H10	0.1825 (6)	0.054 (2)	0.2311 (12)	0.032 (4)*
H11	0.0978 (5)	0.054 (2)	0.1804 (11)	0.021 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0166 (9)	0.0122 (8)	0.0116 (8)	0.0000	0.0000	−0.0017 (6)
C2	0.0164 (6)	0.0132 (6)	0.0127 (6)	0.0011 (5)	0.0009 (4)	−0.0021 (5)
C3	0.0191 (7)	0.0129 (6)	0.0107 (6)	0.0017 (5)	0.0002 (5)	−0.0018 (5)
C4	0.0198 (7)	0.0155 (6)	0.0156 (6)	0.0032 (5)	0.0006 (5)	−0.0005 (5)
C5	0.0265 (7)	0.0129 (6)	0.0163 (6)	0.0041 (5)	−0.0004 (5)	0.0014 (5)
C6	0.0165 (6)	0.0134 (6)	0.0145 (6)	0.0001 (5)	−0.0002 (5)	0.0042 (5)
C7	0.0200 (7)	0.0148 (6)	0.0206 (7)	−0.0003 (5)	0.0024 (5)	0.0011 (5)
C8	0.0184 (7)	0.0206 (7)	0.0286 (7)	0.0027 (5)	0.0051 (5)	0.0044 (6)
C9	0.0148 (7)	0.0302 (8)	0.0282 (7)	−0.0010 (5)	−0.0033 (6)	0.0085 (6)
C10	0.0244 (7)	0.0265 (7)	0.0191 (7)	−0.0033 (6)	−0.0051 (5)	0.0008 (6)
C11	0.0214 (7)	0.0191 (6)	0.0162 (6)	0.0016 (5)	0.0013 (5)	0.0003 (5)

Geometric parameters (Å, º)

C1—C2	1.4282 (14)	C7—C8	1.3864 (19)
C1—C2^i	1.4282 (14)	C8—C9	1.389 (2)
C1—C1^ii	1.466 (2)	C9—C10	1.386 (2)
C2—C3	1.4039 (17)	C10—C11	1.3863 (19)
C2—C6	1.4988 (19)	C4—H4	0.975 (13)
C3—C4	1.4406 (17)	C5—H5	0.961 (14)
C3—C3^iii	1.4348 (19)	C7—H7	0.995 (14)
C4—C5	1.3571 (18)	C8—H8	0.991 (14)
C5—C5^iii	1.4177 (19)	C9—H9	0.966 (16)
C6—C7	1.3962 (18)	C10—H10	0.977 (16)
C6—C11	1.3969 (17)	C11—H11	0.988 (14)
C2···C11^i	3.5807 (18)	C9···H10^vi	2.987 (16)
C4···C7	3.1980 (19)	C9···H8^iv	3.092 (15)
C4···C11	3.5927 (19)	C11···H7^i	3.070 (14)
C6···C6^i	2.8272 (17)	H4···C6	2.468 (14)
C6···C11^i	3.3631 (18)	H4···C7	2.546 (14)
C6···C7^i	3.2412 (18)	H4···H7^vii	2.55 (2)
C7···C4	3.1980 (19)	H5···H11^viii	2.37 (2)
C7···C6^i	3.2412 (18)	H5···C3^vi	3.059 (14)
C7···C11^i	3.2259 (19)	H5···C4^vi	2.935 (14)
C8···C8^iv	3.542 (2)	H7···C7^vii	3.058 (14)
C11···C4	3.5927 (19)	H7···C11^i	3.070 (14)
C11···C6^i	3.3631 (18)	H7···H4^vii	2.55 (2)
C11···C2^i	3.5807 (18)	H7···H7^vii	2.59 (2)
C11···C7^i	3.2259 (19)	H8···H8^vii	2.54 (2)
C3···H5^v	3.059 (14)	H8···C8^iv	2.809 (14)
C4···H5^v	2.935 (14)	H8···C9^iv	3.092 (15)
C4···H11^vi	2.909 (15)	H8···H8^iv	2.28 (2)
C5···H11^vi	2.985 (15)	H10···C9^v	2.987 (16)
C6···H4	2.468 (14)	H11···H5^ix	2.37 (2)
C7···H4	2.546 (14)	H11···C4^v	2.909 (15)
C7···H7^vii	3.058 (14)	H11···C5^v	2.985 (15)
C8···H8^iv	2.809 (14)
C2—C1—C2^i	122.19 (13)	C9—C10—C11	120.01 (13)
C1^ii—C1—C2	118.91 (8)	C6—C11—C10	121.05 (12)
C1^ii—C1—C2^i	118.91 (8)	C3—C4—H4	118.3 (8)
C1—C2—C3	120.50 (12)	C5—C4—H4	119.7 (8)
C1—C2—C6	123.00 (11)	C4—C5—H5	120.9 (8)
C3—C2—C6	116.11 (10)	C5^iii—C5—H5	118.9 (8)
C2—C3—C4	121.78 (12)	C6—C7—H7	119.6 (8)
C2—C3—C3^iii	120.20 (11)	C8—C7—H7	119.8 (8)
C3^iii—C3—C4	117.86 (11)	C7—C8—H8	119.8 (8)
C3—C4—C5	121.97 (12)	C9—C8—H8	119.8 (8)
C4—C5—C5^iii	120.16 (12)	C8—C9—H9	119.7 (9)
C2—C6—C7	122.09 (11)	C10—C9—H9	120.7 (9)
C2—C6—C11	119.16 (11)	C9—C10—H10	119.9 (9)
C7—C6—C11	118.35 (12)	C11—C10—H10	120.1 (9)
C6—C7—C8	120.58 (12)	C6—C11—H11	118.3 (8)
C7—C8—C9	120.41 (12)	C10—C11—H11	120.6 (8)
C8—C9—C10	119.59 (12)
C2^i—C1—C2—C3	−172.76 (9)	C2—C3—C3^iii—C2^iii	0.00 (17)
C2^i—C1—C2—C6	14.70 (13)	C2—C3—C3^iii—C4^iii	−175.43 (11)
C1^ii—C1—C2—C3	7.24 (12)	C4—C3—C3^iii—C2^iii	175.43 (11)
C1^ii—C1—C2—C6	−165.30 (8)	C4—C3—C3^iii—C4^iii	0.00 (16)
C1—C2—C3—C4	177.42 (10)	C3—C4—C5—C5^iii	−1.42 (19)
C1—C2—C3—C3^iii	−7.34 (16)	C4—C5—C5^iii—C4^iii	0.00 (19)
C6—C2—C3—C4	−9.54 (16)	C2—C6—C7—C8	−172.44 (12)
C6—C2—C3—C3^iii	165.71 (10)	C11—C6—C7—C8	0.22 (18)
C1—C2—C6—C7	−110.05 (13)	C2—C6—C11—C10	173.26 (12)
C1—C2—C6—C11	77.35 (14)	C7—C6—C11—C10	0.37 (19)
C3—C2—C6—C7	77.11 (15)	C6—C7—C8—C9	−0.7 (2)
C3—C2—C6—C11	−95.50 (14)	C7—C8—C9—C10	0.5 (2)
C2—C3—C4—C5	176.74 (12)	C8—C9—C10—C11	0.1 (2)
C3^iii—C3—C4—C5	1.39 (18)	C9—C10—C11—C6	−0.5 (2)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) −x+1/2, −y−1/2, −z; (v) x, y+1/2, −z+1/2; (vi) x, y−1/2, −z+1/2; (vii) x, −y−1, −z; (viii) x, y−1, z; (ix) x, y+1, z.

(125K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 4800 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.292 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 4800 reflections
a = 26.789 (4) Å	θ = 2.9–27.5°
b = 7.173 (1) Å	µ = 0.07 mm^−1
c = 14.246 (2) Å	T = 125 K
V = 2737.5 (7) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1428 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1119 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.046
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.2°
phi and ω scans	h = −28→33
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −8→8
Tmin = 0.972, Tmax = 0.998	l = −17→17
10026 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: difference Fourier map
wR(F^2) = 0.101	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 1.7332P] where P = (Fo^2 + 2Fc^2)/3
1428 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02723 (7)	0.00000	0.00000	0.0156 (5)
C2	0.05315 (5)	−0.14435 (18)	0.04909 (9)	0.0160 (4)
C3	0.02670 (5)	−0.29541 (18)	0.08757 (8)	0.0162 (4)
C4	0.05192 (6)	−0.44699 (19)	0.13405 (9)	0.0193 (4)
C5	0.02634 (6)	−0.58862 (18)	0.17511 (9)	0.0213 (4)
C6	0.10755 (5)	−0.13436 (18)	0.07266 (9)	0.0168 (4)
C7	0.14287 (5)	−0.2473 (2)	0.02915 (10)	0.0214 (4)
C8	0.19178 (6)	−0.2505 (2)	0.05983 (11)	0.0265 (5)
C9	0.20663 (6)	−0.1387 (2)	0.13433 (11)	0.0285 (5)
C10	0.17202 (6)	−0.0252 (2)	0.17824 (11)	0.0281 (5)
C11	0.12299 (6)	−0.0236 (2)	0.14796 (9)	0.0218 (4)
H4	0.0882 (6)	−0.445 (2)	0.1358 (10)	0.022 (4)*
H5	0.0442 (5)	−0.688 (2)	0.2072 (11)	0.027 (4)*
H7	0.1324 (6)	−0.325 (2)	−0.0251 (11)	0.023 (4)*
H8	0.2170 (6)	−0.330 (2)	0.0266 (11)	0.034 (5)*
H9	0.2416 (7)	−0.141 (2)	0.1545 (11)	0.033 (4)*
H10	0.1817 (6)	0.056 (2)	0.2302 (13)	0.043 (5)*
H11	0.0976 (6)	0.053 (2)	0.1789 (10)	0.019 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0217 (10)	0.0135 (9)	0.0117 (8)	0.0000	0.0000	−0.0017 (7)
C2	0.0212 (7)	0.0145 (6)	0.0122 (6)	0.0012 (5)	0.0017 (5)	−0.0018 (5)
C3	0.0235 (7)	0.0145 (6)	0.0107 (6)	0.0014 (5)	0.0008 (5)	−0.0017 (5)
C4	0.0247 (8)	0.0178 (7)	0.0155 (6)	0.0040 (6)	0.0010 (6)	0.0005 (5)
C5	0.0327 (8)	0.0149 (6)	0.0163 (7)	0.0044 (6)	0.0005 (6)	0.0022 (5)
C6	0.0196 (7)	0.0164 (6)	0.0145 (6)	0.0003 (5)	−0.0001 (5)	0.0053 (5)
C7	0.0247 (8)	0.0175 (7)	0.0219 (7)	0.0004 (6)	0.0032 (6)	0.0011 (6)
C8	0.0231 (8)	0.0240 (8)	0.0324 (8)	0.0033 (7)	0.0055 (6)	0.0052 (6)
C9	0.0191 (8)	0.0353 (9)	0.0311 (8)	−0.0013 (7)	−0.0036 (6)	0.0095 (7)
C10	0.0313 (9)	0.0326 (9)	0.0205 (7)	−0.0044 (7)	−0.0061 (6)	0.0009 (6)
C11	0.0258 (8)	0.0221 (7)	0.0174 (7)	0.0018 (6)	0.0010 (6)	0.0000 (6)

Geometric parameters (Å, º)

C1—C2	1.4295 (16)	C7—C8	1.381 (2)
C1—C2^i	1.4295 (16)	C8—C9	1.388 (2)
C1—C1^ii	1.459 (3)	C9—C10	1.383 (2)
C2—C3	1.4059 (18)	C10—C11	1.383 (2)
C2—C6	1.4972 (19)	C4—H4	0.972 (16)
C3—C4	1.4412 (19)	C5—H5	0.973 (15)
C3—C3^iii	1.4305 (19)	C7—H7	0.993 (15)
C4—C5	1.358 (2)	C8—H8	1.003 (15)
C5—C5^iii	1.411 (2)	C9—H9	0.980 (19)
C6—C7	1.3913 (19)	C10—H10	0.977 (17)
C6—C11	1.3975 (19)	C11—H11	0.979 (15)
C2···C11^i	3.582 (2)	C8···H8^iv	2.797 (16)
C4···C7	3.197 (2)	C9···H10^vi	2.994 (16)
C4···C11	3.590 (2)	C9···H8^iv	3.081 (16)
C6···C6^i	2.8286 (19)	C11···H7^i	3.063 (15)
C6···C11^i	3.3665 (19)	H4···C6	2.458 (14)
C6···C7^i	3.239 (2)	H4···C7	2.543 (15)
C7···C4	3.197 (2)	H4···H7^vii	2.57 (2)
C7···C6^i	3.239 (2)	H5···H11^viii	2.38 (2)
C7···C11^i	3.229 (2)	H5···C3^vi	3.060 (16)
C8···C8^iv	3.555 (2)	H5···C4^vi	2.934 (15)
C11···C4	3.590 (2)	H7···C7^vii	3.081 (14)
C11···C6^i	3.3665 (19)	H7···C11^i	3.063 (15)
C11···C2^i	3.582 (2)	H7···H4^vii	2.57 (2)
C11···C7^i	3.229 (2)	H8···H8^vii	2.55 (2)
C3···H5^v	3.060 (16)	H8···C8^iv	2.797 (16)
C4···H5^v	2.934 (15)	H8···C9^iv	3.081 (16)
C4···H11^vi	2.932 (15)	H8···H8^iv	2.24 (2)
C5···H11^vi	3.000 (15)	H10···C9^v	2.994 (16)
C6···H4	2.458 (14)	H11···H5^ix	2.38 (2)
C7···H4	2.543 (15)	H11···C4^v	2.932 (15)
C7···H7^vii	3.081 (14)	H11···C5^v	3.000 (15)
C2—C1—C2^i	121.88 (15)	C9—C10—C11	120.04 (14)
C1^ii—C1—C2	119.06 (8)	C6—C11—C10	121.06 (14)
C1^ii—C1—C2^i	119.06 (8)	C3—C4—H4	118.0 (9)
C1—C2—C3	120.28 (13)	C5—C4—H4	120.3 (9)
C1—C2—C6	123.22 (12)	C4—C5—H5	120.2 (8)
C3—C2—C6	116.10 (11)	C5^iii—C5—H5	119.5 (8)
C2—C3—C4	121.62 (12)	C6—C7—H7	118.8 (9)
C2—C3—C3^iii	120.26 (12)	C8—C7—H7	120.3 (9)
C3^iii—C3—C4	117.96 (12)	C7—C8—H8	119.9 (9)
C3—C4—C5	121.72 (14)	C9—C8—H8	119.8 (9)
C4—C5—C5^iii	120.31 (13)	C8—C9—H9	119.2 (9)
C2—C6—C7	122.29 (12)	C10—C9—H9	121.2 (9)
C2—C6—C11	119.17 (12)	C9—C10—H10	121.0 (9)
C7—C6—C11	118.15 (13)	C11—C10—H10	118.9 (9)
C6—C7—C8	120.91 (13)	C6—C11—H11	117.3 (9)
C7—C8—C9	120.27 (14)	C10—C11—H11	121.6 (9)
C8—C9—C10	119.57 (15)
C2^i—C1—C2—C3	−172.80 (10)	C2—C3—C3^iii—C2^iii	0.00 (18)
C2^i—C1—C2—C6	14.73 (15)	C2—C3—C3^iii—C4^iii	−175.49 (11)
C1^ii—C1—C2—C3	7.20 (13)	C4—C3—C3^iii—C2^iii	175.49 (11)
C1^ii—C1—C2—C6	−165.28 (9)	C4—C3—C3^iii—C4^iii	0.00 (17)
C1—C2—C3—C4	177.39 (10)	C3—C4—C5—C5^iii	−1.5 (2)
C1—C2—C3—C3^iii	−7.29 (17)	C4—C5—C5^iii—C4^iii	0.0 (2)
C6—C2—C3—C4	−9.62 (18)	C2—C6—C7—C8	−172.42 (13)
C6—C2—C3—C3^iii	165.71 (11)	C11—C6—C7—C8	0.3 (2)
C1—C2—C6—C7	−109.97 (14)	C2—C6—C11—C10	173.27 (13)
C1—C2—C6—C11	77.38 (16)	C7—C6—C11—C10	0.3 (2)
C3—C2—C6—C7	77.27 (16)	C6—C7—C8—C9	−0.8 (2)
C3—C2—C6—C11	−95.38 (15)	C7—C8—C9—C10	0.6 (2)
C2—C3—C4—C5	176.86 (12)	C8—C9—C10—C11	0.0 (2)
C3^iii—C3—C4—C5	1.43 (18)	C9—C10—C11—C6	−0.5 (2)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) −x+1/2, −y−1/2, −z; (v) x, y+1/2, −z+1/2; (vi) x, y−1/2, −z+1/2; (vii) x, −y−1, −z; (viii) x, y−1, z; (ix) x, y+1, z.

(150K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 4648 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.293 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 4648 reflections
a = 26.775 (4) Å	θ = 2.9–27.5°
b = 7.168 (1) Å	µ = 0.07 mm^−1
c = 14.258 (2) Å	T = 150 K
V = 2736.4 (7) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1427 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1101 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.045
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.2°
phi and ω scans	h = −33→28
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −8→8
Tmin = 0.974, Tmax = 0.998	l = −17→17
10088 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.105	All H-atom parameters refined
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0526P)^2 + 1.7289P] where P = (Fo^2 + 2Fc^2)/3
1427 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02727 (7)	0.00000	0.00000	0.0172 (5)
C2	0.05307 (5)	−0.14417 (18)	0.04907 (9)	0.0177 (4)
C3	0.02670 (5)	−0.29515 (18)	0.08757 (8)	0.0181 (4)
C4	0.05186 (6)	−0.44662 (19)	0.13409 (9)	0.0220 (4)
C5	0.02630 (6)	−0.58805 (19)	0.17505 (10)	0.0242 (4)
C6	0.10744 (5)	−0.13413 (18)	0.07267 (9)	0.0191 (4)
C7	0.14283 (5)	−0.2470 (2)	0.02912 (10)	0.0242 (4)
C8	0.19169 (6)	−0.2498 (2)	0.06004 (12)	0.0306 (5)
C9	0.20647 (6)	−0.1379 (2)	0.13425 (11)	0.0335 (5)
C10	0.17191 (6)	−0.0249 (2)	0.17798 (11)	0.0324 (5)
C11	0.12289 (6)	−0.0237 (2)	0.14788 (10)	0.0252 (4)
H4	0.0877 (6)	−0.448 (2)	0.1341 (11)	0.023 (4)*
H5	0.0447 (6)	−0.688 (2)	0.2071 (11)	0.031 (4)*
H7	0.1328 (6)	−0.324 (2)	−0.0250 (11)	0.031 (4)*
H8	0.2163 (6)	−0.330 (2)	0.0272 (12)	0.038 (5)*
H9	0.2412 (7)	−0.142 (2)	0.1537 (12)	0.043 (5)*
H10	0.1813 (7)	0.055 (3)	0.2297 (14)	0.048 (5)*
H11	0.0976 (6)	0.053 (2)	0.1778 (11)	0.026 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0227 (10)	0.0165 (9)	0.0125 (8)	0.0000	0.0000	−0.0024 (7)
C2	0.0228 (8)	0.0167 (6)	0.0136 (6)	0.0018 (5)	0.0015 (5)	−0.0016 (5)
C3	0.0253 (7)	0.0171 (7)	0.0118 (6)	0.0023 (5)	0.0008 (5)	−0.0018 (5)
C4	0.0270 (9)	0.0210 (7)	0.0179 (7)	0.0047 (6)	0.0012 (6)	0.0012 (6)
C5	0.0358 (9)	0.0179 (7)	0.0190 (7)	0.0051 (6)	0.0002 (6)	0.0035 (5)
C6	0.0220 (8)	0.0190 (7)	0.0162 (6)	0.0004 (6)	−0.0004 (5)	0.0053 (5)
C7	0.0268 (8)	0.0209 (7)	0.0248 (7)	0.0006 (6)	0.0032 (6)	0.0018 (6)
C8	0.0234 (8)	0.0304 (8)	0.0379 (9)	0.0032 (7)	0.0066 (7)	0.0065 (7)
C9	0.0216 (9)	0.0428 (9)	0.0361 (9)	−0.0010 (7)	−0.0048 (7)	0.0119 (8)
C10	0.0332 (9)	0.0402 (9)	0.0237 (8)	−0.0050 (8)	−0.0074 (7)	0.0005 (7)
C11	0.0287 (8)	0.0275 (8)	0.0194 (7)	0.0022 (7)	−0.0001 (6)	−0.0007 (6)

Geometric parameters (Å, º)

C1—C2	1.4264 (16)	C7—C8	1.381 (2)
C1—C2^i	1.4264 (16)	C8—C9	1.386 (2)
C1—C1^ii	1.460 (3)	C9—C10	1.379 (2)
C2—C3	1.4039 (18)	C10—C11	1.381 (2)
C2—C6	1.4959 (19)	C4—H4	0.960 (16)
C3—C4	1.4397 (19)	C5—H5	0.982 (15)
C3—C3^iii	1.4298 (19)	C7—H7	0.986 (15)
C4—C5	1.355 (2)	C8—H8	0.992 (16)
C5—C5^iii	1.408 (2)	C9—H9	0.971 (19)
C6—C7	1.3921 (19)	C10—H10	0.97 (2)
C6—C11	1.3956 (19)	C11—H11	0.971 (16)
C2···C11^i	3.582 (2)	C7···H7^vii	3.087 (14)
C4···C7	3.197 (2)	C8···H8^iv	2.818 (16)
C4···C11	3.584 (2)	C9···H10^vi	3.01 (2)
C6···C6^i	2.8270 (19)	C11···H7^i	3.058 (15)
C6···C11^i	3.367 (2)	H4···C6	2.472 (15)
C6···C7^i	3.235 (2)	H4···C7	2.549 (15)
C7···C4	3.197 (2)	H4···H7^vii	2.56 (2)
C7···C6^i	3.235 (2)	H5···H11^viii	2.37 (2)
C7···C11^i	3.228 (2)	H5···C3^vi	3.065 (16)
C8···C8^iv	3.561 (2)	H5···C4^vi	2.933 (15)
C11···C2^i	3.582 (2)	H7···C7^vii	3.087 (14)
C11···C4	3.584 (2)	H7···C11^i	3.058 (15)
C11···C6^i	3.367 (2)	H7···H4^vii	2.56 (2)
C11···C7^i	3.228 (2)	H8···H8^vii	2.56 (2)
C3···H5^v	3.065 (16)	H8···C8^iv	2.818 (16)
C4···H5^v	2.933 (15)	H8···H8^iv	2.28 (2)
C4···H11^vi	2.949 (16)	H10···C9^v	3.01 (2)
C5···H11^vi	3.011 (16)	H11···H5^ix	2.37 (2)
C6···H4	2.472 (15)	H11···C4^v	2.949 (16)
C7···H4	2.549 (15)	H11···C5^v	3.011 (16)
C2—C1—C2^i	122.07 (15)	C9—C10—C11	120.07 (14)
C1^ii—C1—C2	118.97 (8)	C6—C11—C10	121.13 (14)
C1^ii—C1—C2^i	118.97 (8)	C3—C4—H4	118.4 (9)
C1—C2—C3	120.44 (13)	C5—C4—H4	119.8 (9)
C1—C2—C6	123.15 (12)	C4—C5—H5	119.5 (9)
C3—C2—C6	116.01 (11)	C5^iii—C5—H5	120.1 (9)
C2—C3—C4	121.75 (12)	C6—C7—H7	119.3 (9)
C2—C3—C3^iii	120.19 (12)	C8—C7—H7	120.0 (9)
C3^iii—C3—C4	117.90 (12)	C7—C8—H8	119.2 (10)
C3—C4—C5	121.76 (14)	C9—C8—H8	120.4 (10)
C4—C5—C5^iii	120.33 (13)	C8—C9—H9	118.3 (9)
C2—C6—C7	122.28 (12)	C10—C9—H9	122.1 (10)
C2—C6—C11	119.25 (12)	C9—C10—H10	121.2 (11)
C7—C6—C11	118.07 (13)	C11—C10—H10	118.7 (11)
C6—C7—C8	120.73 (13)	C6—C11—H11	116.9 (9)
C7—C8—C9	120.40 (14)	C10—C11—H11	122.0 (9)
C8—C9—C10	119.59 (15)
C2^i—C1—C2—C3	−172.78 (10)	C2—C3—C3^iii—C2^iii	0.00 (18)
C2^i—C1—C2—C6	14.76 (15)	C2—C3—C3^iii—C4^iii	−175.47 (11)
C1^ii—C1—C2—C3	7.22 (13)	C4—C3—C3^iii—C2^iii	175.47 (11)
C1^ii—C1—C2—C6	−165.25 (9)	C4—C3—C3^iii—C4^iii	0.00 (17)
C1—C2—C3—C4	177.39 (10)	C3—C4—C5—C5^iii	−1.5 (2)
C1—C2—C3—C3^iii	−7.31 (17)	C4—C5—C5^iii—C4^iii	0.0 (2)
C6—C2—C3—C4	−9.62 (18)	C2—C6—C7—C8	−172.41 (13)
C6—C2—C3—C3^iii	165.67 (11)	C11—C6—C7—C8	0.3 (2)
C1—C2—C6—C7	−109.81 (14)	C2—C6—C11—C10	173.45 (13)
C1—C2—C6—C11	77.54 (16)	C7—C6—C11—C10	0.5 (2)
C3—C2—C6—C7	77.42 (16)	C6—C7—C8—C9	−1.0 (2)
C3—C2—C6—C11	−95.24 (15)	C7—C8—C9—C10	0.8 (2)
C2—C3—C4—C5	176.90 (13)	C8—C9—C10—C11	0.1 (2)
C3^iii—C3—C4—C5	1.50 (19)	C9—C10—C11—C6	−0.7 (2)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) −x+1/2, −y−1/2, −z; (v) x, y+1/2, −z+1/2; (vi) x, y−1/2, −z+1/2; (vii) x, −y−1, −z; (viii) x, y−1, z; (ix) x, y+1, z.

(175K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 4431 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.284 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 4431 reflections
a = 26.828 (4) Å	θ = 2.9–27.5°
b = 7.181 (1) Å	µ = 0.07 mm^−1
c = 14.306 (2) Å	T = 175 K
V = 2756.1 (7) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1434 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1085 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.046
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.2°
phi and ω scans	h = −33→28
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −8→8
Tmin = 0.961, Tmax = 0.998	l = −17→17
10119 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.039	Hydrogen site location: difference Fourier map
wR(F^2) = 0.100	All H-atom parameters refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0492P)^2 + 1.0967P] where P = (Fo^2 + 2Fc^2)/3
1434 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02718 (7)	0.00000	0.00000	0.0197 (5)
C2	0.05303 (5)	−0.14399 (17)	0.04909 (8)	0.0206 (4)
C3	0.02673 (5)	−0.29472 (17)	0.08762 (8)	0.0206 (4)
C4	0.05186 (6)	−0.44615 (18)	0.13392 (9)	0.0251 (4)
C5	0.02622 (6)	−0.58729 (19)	0.17496 (9)	0.0282 (4)
C6	0.10736 (5)	−0.13391 (18)	0.07267 (9)	0.0216 (4)
C7	0.14277 (5)	−0.24639 (19)	0.02938 (10)	0.0278 (4)
C8	0.19159 (6)	−0.2491 (2)	0.06005 (11)	0.0353 (5)
C9	0.20620 (6)	−0.1376 (2)	0.13407 (11)	0.0388 (5)
C10	0.17173 (6)	−0.0245 (2)	0.17770 (11)	0.0379 (5)
C11	0.12281 (6)	−0.0235 (2)	0.14762 (9)	0.0290 (5)
H4	0.0886 (6)	−0.447 (2)	0.1352 (10)	0.031 (4)*
H5	0.0443 (5)	−0.686 (2)	0.2063 (10)	0.034 (4)*
H7	0.1330 (6)	−0.324 (2)	−0.0237 (11)	0.035 (4)*
H8	0.2168 (6)	−0.328 (2)	0.0272 (11)	0.048 (5)*
H9	0.2406 (7)	−0.139 (2)	0.1527 (11)	0.043 (5)*
H10	0.1809 (6)	0.056 (2)	0.2295 (13)	0.054 (5)*
H11	0.0975 (5)	0.053 (2)	0.1780 (10)	0.027 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0248 (10)	0.0196 (9)	0.0148 (8)	0.0000	0.0000	−0.0019 (7)
C2	0.0262 (8)	0.0201 (6)	0.0154 (6)	0.0019 (5)	0.0016 (5)	−0.0015 (5)
C3	0.0285 (7)	0.0203 (6)	0.0130 (6)	0.0015 (5)	0.0006 (5)	−0.0019 (5)
C4	0.0307 (9)	0.0243 (7)	0.0204 (7)	0.0055 (6)	0.0017 (6)	0.0012 (5)
C5	0.0409 (9)	0.0214 (7)	0.0223 (7)	0.0054 (6)	0.0001 (6)	0.0039 (5)
C6	0.0236 (8)	0.0227 (6)	0.0186 (6)	0.0009 (5)	−0.0003 (5)	0.0055 (5)
C7	0.0295 (8)	0.0250 (7)	0.0288 (7)	0.0013 (6)	0.0037 (6)	0.0013 (6)
C8	0.0271 (8)	0.0364 (8)	0.0424 (9)	0.0040 (7)	0.0070 (7)	0.0064 (7)
C9	0.0230 (9)	0.0513 (10)	0.0420 (9)	−0.0006 (7)	−0.0062 (7)	0.0133 (8)
C10	0.0374 (10)	0.0486 (10)	0.0278 (8)	−0.0049 (8)	−0.0092 (7)	0.0002 (7)
C11	0.0320 (9)	0.0340 (8)	0.0211 (7)	0.0030 (7)	0.0000 (6)	−0.0012 (6)

Geometric parameters (Å, º)

C1—C2	1.4294 (15)	C7—C8	1.381 (2)
C1—C2^i	1.4294 (15)	C8—C9	1.384 (2)
C1—C1^ii	1.458 (3)	C9—C10	1.380 (2)
C2—C3	1.4047 (18)	C10—C11	1.381 (2)
C2—C6	1.4978 (19)	C4—H4	0.986 (16)
C3—C4	1.4407 (19)	C5—H5	0.969 (14)
C3—C3^iii	1.4342 (19)	C7—H7	0.978 (15)
C4—C5	1.358 (2)	C8—H8	1.000 (16)
C5—C5^iii	1.407 (2)	C9—H9	0.961 (19)
C6—C7	1.3923 (19)	C10—H10	0.972 (17)
C6—C11	1.3965 (19)	C11—H11	0.976 (14)
C2···C11^i	3.5876 (19)	C7···H7^vii	3.097 (14)
C4···C7	3.200 (2)	C8···H8^iv	2.812 (16)
C4···C11	3.588 (2)	C9···H10^vi	3.019 (16)
C6···C6^i	2.8323 (19)	C11···H7^i	3.073 (15)
C6···C11^i	3.3736 (19)	H4···C6	2.472 (14)
C6···C7^i	3.239 (2)	H4···C7	2.545 (15)
C7···C4	3.200 (2)	H4···H7^vii	2.58 (2)
C7···C6^i	3.239 (2)	H5···H11^viii	2.39 (2)
C7···C11^i	3.233 (2)	H5···C3^vi	3.086 (14)
C8···C8^iv	3.574 (2)	H5···C4^vi	2.959 (14)
C11···C2^i	3.5876 (19)	H7···C7^vii	3.097 (14)
C11···C4	3.588 (2)	H7···C11^i	3.073 (15)
C11···C6^i	3.3736 (19)	H7···H4^vii	2.58 (2)
C11···C7^i	3.233 (2)	H8···H8^vii	2.59 (2)
C3···H5^v	3.086 (14)	H8···C8^iv	2.812 (16)
C4···H5^v	2.959 (14)	H8···H8^iv	2.24 (2)
C4···H11^vi	2.956 (14)	H10···C9^v	3.019 (16)
C5···H11^vi	3.016 (14)	H11···H5^ix	2.39 (2)
C6···H4	2.472 (14)	H11···C4^v	2.956 (14)
C7···H4	2.545 (15)	H11···C5^v	3.016 (14)
C2—C1—C2^i	121.95 (15)	C9—C10—C11	119.93 (14)
C1^ii—C1—C2	119.02 (8)	C6—C11—C10	121.22 (14)
C1^ii—C1—C2^i	119.02 (8)	C3—C4—H4	118.8 (8)
C1—C2—C3	120.43 (13)	C5—C4—H4	119.6 (8)
C1—C2—C6	123.22 (12)	C4—C5—H5	119.5 (8)
C3—C2—C6	115.95 (11)	C5^iii—C5—H5	120.0 (8)
C2—C3—C4	121.80 (12)	C6—C7—H7	119.6 (9)
C2—C3—C3^iii	120.15 (11)	C8—C7—H7	119.5 (9)
C3^iii—C3—C4	117.90 (12)	C7—C8—H8	120.0 (9)
C3—C4—C5	121.66 (14)	C9—C8—H8	119.7 (9)
C4—C5—C5^iii	120.42 (13)	C8—C9—H9	118.6 (9)
C2—C6—C7	122.40 (12)	C10—C9—H9	121.6 (9)
C2—C6—C11	119.29 (12)	C9—C10—H10	121.7 (9)
C7—C6—C11	117.93 (13)	C11—C10—H10	118.4 (9)
C6—C7—C8	120.92 (13)	C6—C11—H11	117.1 (8)
C7—C8—C9	120.22 (14)	C10—C11—H11	121.7 (8)
C8—C9—C10	119.78 (15)
C2^i—C1—C2—C3	−172.78 (10)	C2—C3—C3^iii—C2^iii	0.02 (18)
C2^i—C1—C2—C6	14.78 (14)	C2—C3—C3^iii—C4^iii	−175.64 (11)
C1^ii—C1—C2—C3	7.22 (12)	C4—C3—C3^iii—C2^iii	175.64 (11)
C1^ii—C1—C2—C6	−165.22 (8)	C4—C3—C3^iii—C4^iii	0.02 (18)
C1—C2—C3—C4	177.23 (10)	C3—C4—C5—C5^iii	−1.3 (2)
C1—C2—C3—C3^iii	−7.30 (16)	C4—C5—C5^iii—C4^iii	0.0 (2)
C6—C2—C3—C4	−9.80 (17)	C2—C6—C7—C8	−172.50 (13)
C6—C2—C3—C3^iii	165.67 (11)	C11—C6—C7—C8	0.3 (2)
C1—C2—C6—C7	−109.75 (14)	C2—C6—C11—C10	173.46 (13)
C1—C2—C6—C11	77.54 (15)	C7—C6—C11—C10	0.4 (2)
C3—C2—C6—C7	77.51 (16)	C6—C7—C8—C9	−0.8 (2)
C3—C2—C6—C11	−95.21 (15)	C7—C8—C9—C10	0.5 (2)
C2—C3—C4—C5	176.85 (12)	C8—C9—C10—C11	0.2 (2)
C3^iii—C3—C4—C5	1.28 (18)	C9—C10—C11—C6	−0.7 (2)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) −x+1/2, −y−1/2, −z; (v) x, y+1/2, −z+1/2; (vi) x, y−1/2, −z+1/2; (vii) x, −y−1, −z; (viii) x, y−1, z; (ix) x, y+1, z.

(200K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 4251 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.281 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 4251 reflections
a = 26.838 (4) Å	θ = 2.8–27.4°
b = 7.181 (1) Å	µ = 0.07 mm^−1
c = 14.332 (2) Å	T = 200 K
V = 2762.1 (7) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1437 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1075 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.045
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.2°
phi and ω scans	h = −33→28
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −8→8
Tmin = 0.956, Tmax = 0.996	l = −17→17
10162 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0595P)^2 + 1.3599P] where P = (Fo^2 + 2Fc^2)/3
1437 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02718 (7)	0.00000	0.00000	0.0215 (6)
C2	0.05301 (5)	−0.14396 (19)	0.04907 (9)	0.0221 (4)
C3	0.02666 (5)	−0.29437 (19)	0.08762 (9)	0.0224 (4)
C4	0.05171 (6)	−0.4456 (2)	0.13397 (10)	0.0275 (5)
C5	0.02627 (6)	−0.5864 (2)	0.17497 (10)	0.0315 (5)
C6	0.10730 (5)	−0.13351 (19)	0.07261 (9)	0.0236 (4)
C7	0.14271 (6)	−0.2461 (2)	0.02964 (11)	0.0310 (5)
C8	0.19149 (6)	−0.2484 (3)	0.06023 (13)	0.0401 (6)
C9	0.20606 (7)	−0.1373 (3)	0.13390 (13)	0.0442 (6)
C10	0.17164 (7)	−0.0244 (3)	0.17747 (12)	0.0430 (6)
C11	0.12264 (6)	−0.0233 (2)	0.14730 (10)	0.0320 (5)
H4	0.0880 (7)	−0.443 (2)	0.1341 (12)	0.034 (5)*
H5	0.0447 (6)	−0.686 (2)	0.2055 (12)	0.038 (5)*
H7	0.1325 (6)	−0.324 (2)	−0.0239 (11)	0.032 (4)*
H8	0.2169 (7)	−0.328 (3)	0.0280 (13)	0.055 (6)*
H9	0.2407 (8)	−0.139 (2)	0.1536 (12)	0.053 (5)*
H10	0.1809 (8)	0.057 (3)	0.2298 (16)	0.068 (6)*
H11	0.0971 (6)	0.052 (2)	0.1789 (12)	0.035 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0261 (11)	0.0214 (10)	0.0169 (9)	0.0000	0.0000	−0.0021 (7)
C2	0.0268 (8)	0.0222 (7)	0.0172 (7)	0.0029 (6)	0.0017 (5)	−0.0014 (5)
C3	0.0304 (8)	0.0223 (7)	0.0146 (6)	0.0020 (6)	0.0007 (5)	−0.0020 (5)
C4	0.0325 (10)	0.0262 (7)	0.0239 (7)	0.0053 (6)	0.0022 (7)	0.0025 (6)
C5	0.0441 (9)	0.0243 (7)	0.0260 (8)	0.0064 (7)	0.0008 (7)	0.0052 (6)
C6	0.0258 (8)	0.0243 (7)	0.0208 (7)	0.0012 (6)	0.0002 (6)	0.0065 (5)
C7	0.0312 (9)	0.0285 (8)	0.0333 (8)	0.0015 (7)	0.0049 (7)	0.0011 (7)
C8	0.0286 (9)	0.0419 (10)	0.0499 (11)	0.0046 (8)	0.0079 (8)	0.0082 (8)
C9	0.0256 (10)	0.0589 (12)	0.0482 (11)	−0.0010 (9)	−0.0069 (8)	0.0147 (9)
C10	0.0415 (11)	0.0562 (11)	0.0312 (9)	−0.0063 (9)	−0.0103 (8)	0.0009 (8)
C11	0.0335 (9)	0.0384 (9)	0.0241 (7)	0.0026 (7)	−0.0002 (7)	−0.0013 (7)

Geometric parameters (Å, º)

C1—C2	1.4296 (16)	C7—C8	1.381 (2)
C1—C2^i	1.4296 (16)	C8—C9	1.380 (3)
C1—C1^ii	1.459 (3)	C9—C10	1.379 (3)
C2—C3	1.4043 (19)	C10—C11	1.384 (2)
C2—C6	1.4975 (19)	C4—H4	0.974 (19)
C3—C4	1.440 (2)	C5—H5	0.974 (16)
C3—C3^iii	1.4310 (19)	C7—H7	0.988 (15)
C4—C5	1.354 (2)	C8—H8	1.00 (2)
C5—C5^iii	1.410 (2)	C9—H9	0.97 (2)
C6—C7	1.391 (2)	C10—H10	0.98 (2)
C6—C11	1.394 (2)	C11—H11	0.984 (16)
C2···C11^i	3.586 (2)	C7···H4	2.529 (17)
C4···C7	3.202 (2)	C8···H8^iv	2.819 (19)
C4···C11	3.586 (2)	C9···H10^v	3.02 (2)
C6···C11^i	3.372 (2)	C11···H7^i	3.069 (15)
C6···C6^i	2.8299 (19)	H4···C6	2.446 (15)
C6···C7^i	3.238 (2)	H4···C7	2.529 (17)
C7···C4	3.202 (2)	H4···H7^vii	2.59 (2)
C7···C6^i	3.238 (2)	H5···H11^viii	2.38 (2)
C7···C11^i	3.235 (2)	H5···C4^v	2.967 (16)
C8···C8^iv	3.584 (2)	H7···C11^i	3.069 (15)
C11···C6^i	3.372 (2)	H7···H4^vii	2.59 (2)
C11···C2^i	3.586 (2)	H8···H8^vii	2.60 (3)
C11···C7^i	3.235 (2)	H8···C8^iv	2.819 (19)
C11···C4	3.586 (2)	H8···H8^iv	2.25 (3)
C4···H11^v	2.946 (17)	H10···C9^vi	3.02 (2)
C4···H5^vi	2.967 (16)	H11···H5^ix	2.38 (2)
C5···H11^v	2.998 (17)	H11···C4^vi	2.946 (17)
C6···H4	2.446 (15)	H11···C5^vi	2.998 (17)
C2—C1—C2^i	121.99 (15)	C9—C10—C11	119.90 (17)
C1^ii—C1—C2	119.01 (9)	C6—C11—C10	121.16 (15)
C1^ii—C1—C2^i	119.01 (9)	C3—C4—H4	117.0 (9)
C1—C2—C3	120.37 (13)	C5—C4—H4	121.2 (9)
C1—C2—C6	123.12 (12)	C4—C5—H5	119.2 (9)
C3—C2—C6	116.10 (12)	C5^iii—C5—H5	120.5 (9)
C2—C3—C4	121.77 (13)	C6—C7—H7	118.9 (9)
C2—C3—C3^iii	120.24 (12)	C8—C7—H7	120.2 (9)
C3^iii—C3—C4	117.84 (12)	C7—C8—H8	120.4 (11)
C3—C4—C5	121.87 (14)	C9—C8—H8	119.3 (11)
C4—C5—C5^iii	120.28 (14)	C8—C9—H9	119.1 (10)
C2—C6—C7	122.39 (12)	C10—C9—H9	121.1 (10)
C2—C6—C11	119.28 (12)	C9—C10—H10	121.7 (13)
C7—C6—C11	117.92 (13)	C11—C10—H10	118.4 (13)
C6—C7—C8	120.93 (15)	C6—C11—H11	117.4 (10)
C7—C8—C9	120.31 (17)	C10—C11—H11	121.4 (10)
C8—C9—C10	119.78 (17)
C2^i—C1—C2—C3	−172.85 (11)	C2—C3—C3^iii—C2^iii	0.00 (19)
C2^i—C1—C2—C6	14.84 (15)	C2—C3—C3^iii—C4^iii	−175.64 (12)
C1^ii—C1—C2—C3	7.15 (14)	C4—C3—C3^iii—C2^iii	175.64 (12)
C1^ii—C1—C2—C6	−165.16 (9)	C4—C3—C3^iii—C4^iii	0.00 (19)
C1—C2—C3—C4	177.30 (11)	C3—C4—C5—C5^iii	−1.3 (2)
C1—C2—C3—C3^iii	−7.23 (18)	C4—C5—C5^iii—C4^iii	0.0 (2)
C6—C2—C3—C4	−9.87 (19)	C2—C6—C7—C8	−172.52 (15)
C6—C2—C3—C3^iii	165.60 (12)	C11—C6—C7—C8	0.1 (2)
C1—C2—C6—C7	−109.92 (15)	C2—C6—C11—C10	173.32 (15)
C1—C2—C6—C11	77.61 (16)	C7—C6—C11—C10	0.5 (2)
C3—C2—C6—C7	77.47 (17)	C6—C7—C8—C9	−0.5 (3)
C3—C2—C6—C11	−95.00 (16)	C7—C8—C9—C10	0.4 (3)
C2—C3—C4—C5	176.88 (13)	C8—C9—C10—C11	0.2 (3)
C3^iii—C3—C4—C5	1.3 (2)	C9—C10—C11—C6	−0.6 (3)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) −x+1/2, −y−1/2, −z; (v) x, y−1/2, −z+1/2; (vi) x, y+1/2, −z+1/2; (vii) x, −y−1, −z; (viii) x, y−1, z; (ix) x, y+1, z.

(235K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 3849 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.282 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 3849 reflections
a = 26.818 (5) Å	θ = 2.8–27.4°
b = 7.174 (1) Å	µ = 0.07 mm^−1
c = 14.348 (3) Å	T = 235 K
V = 2760.5 (9) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1437 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	997 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.052
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.0°
phi and ω scans	h = −33→33
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −8→8
Tmin = 0.952, Tmax = 0.992	l = −16→17
10021 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: difference Fourier map
wR(F^2) = 0.109	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0433P)^2 + 2.1676P] where P = (Fo^2 + 2Fc^2)/3
1437 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02725 (7)	0.00000	0.00000	0.0237 (7)
C2	0.05282 (5)	−0.1437 (2)	0.04905 (11)	0.0246 (5)
C3	0.02673 (5)	−0.2940 (2)	0.08752 (10)	0.0247 (5)
C4	0.05163 (6)	−0.4448 (2)	0.13381 (12)	0.0311 (5)
C5	0.02624 (7)	−0.5852 (2)	0.17462 (12)	0.0355 (6)
C6	0.10725 (6)	−0.1332 (2)	0.07259 (11)	0.0265 (5)
C7	0.14260 (6)	−0.2455 (3)	0.02974 (13)	0.0342 (6)
C8	0.19131 (6)	−0.2471 (3)	0.06057 (15)	0.0459 (7)
C9	0.20583 (7)	−0.1364 (3)	0.13366 (15)	0.0505 (7)
C10	0.17143 (7)	−0.0242 (3)	0.17699 (14)	0.0497 (7)
C11	0.12234 (7)	−0.0230 (3)	0.14690 (12)	0.0364 (6)
H4	0.0880 (6)	−0.443 (2)	0.1359 (12)	0.033 (5)*
H5	0.0443 (6)	−0.682 (3)	0.2055 (12)	0.042 (5)*
H7	0.1326 (6)	−0.324 (2)	−0.0238 (12)	0.032 (5)*
H8	0.2163 (7)	−0.325 (3)	0.0277 (13)	0.055 (6)*
H9	0.2410 (8)	−0.137 (3)	0.1527 (13)	0.060 (6)*
H10	0.1796 (7)	0.052 (3)	0.2290 (15)	0.060 (6)*
H11	0.0971 (7)	0.054 (3)	0.1768 (13)	0.041 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0276 (11)	0.0238 (12)	0.0198 (11)	0.0000	0.0000	−0.0019 (9)
C2	0.0285 (8)	0.0245 (8)	0.0207 (8)	0.0034 (7)	0.0011 (6)	−0.0014 (7)
C3	0.0322 (8)	0.0234 (8)	0.0185 (8)	0.0016 (7)	0.0015 (6)	−0.0018 (6)
C4	0.0349 (9)	0.0286 (9)	0.0297 (9)	0.0060 (7)	0.0020 (7)	0.0032 (8)
C5	0.0483 (10)	0.0258 (9)	0.0323 (10)	0.0064 (8)	0.0013 (8)	0.0070 (8)
C6	0.0278 (8)	0.0276 (9)	0.0241 (8)	0.0013 (7)	−0.0002 (6)	0.0059 (7)
C7	0.0319 (9)	0.0312 (10)	0.0395 (11)	0.0022 (8)	0.0055 (8)	0.0008 (8)
C8	0.0302 (9)	0.0481 (12)	0.0595 (14)	0.0061 (9)	0.0090 (9)	0.0093 (11)
C9	0.0276 (10)	0.0661 (14)	0.0579 (14)	−0.0019 (10)	−0.0065 (9)	0.0168 (12)
C10	0.0466 (11)	0.0660 (15)	0.0364 (11)	−0.0077 (11)	−0.0132 (9)	0.0001 (11)
C11	0.0367 (9)	0.0429 (11)	0.0296 (9)	0.0027 (8)	−0.0011 (8)	−0.0012 (8)

Geometric parameters (Å, º)

C1—C2	1.4242 (17)	C7—C8	1.379 (2)
C1—C2^i	1.4242 (17)	C8—C9	1.372 (3)
C1—C1^ii	1.462 (3)	C9—C10	1.373 (3)
C2—C3	1.399 (2)	C10—C11	1.386 (3)
C2—C6	1.500 (2)	C4—H4	0.976 (16)
C3—C4	1.434 (2)	C5—H5	0.956 (19)
C3—C3^iii	1.4337 (19)	C7—H7	0.990 (16)
C4—C5	1.349 (2)	C8—H8	0.99 (2)
C5—C5^iii	1.407 (3)	C9—H9	0.98 (2)
C6—C7	1.388 (2)	C10—H10	0.95 (2)
C6—C11	1.388 (2)	C11—H11	0.97 (2)
C2···C11^i	3.579 (2)	C6···H4	2.456 (15)
C4···C7	3.198 (2)	C7···H4	2.544 (16)
C4···C11	3.576 (3)	C8···H8^iv	2.830 (19)
C6···C11^i	3.367 (2)	C9···H10^v	3.06 (2)
C6···C6^i	2.827 (2)	C11···H7^i	3.065 (16)
C6···C7^i	3.230 (3)	H4···C6	2.456 (15)
C7···C4	3.198 (2)	H4···C7	2.544 (16)
C7···C6^i	3.230 (3)	H5···H11^vii	2.40 (3)
C7···C11^i	3.229 (3)	H5···C4^v	2.985 (19)
C8···C8^iv	3.596 (3)	H7···C11^i	3.065 (16)
C11···C6^i	3.367 (2)	H8···C8^iv	2.830 (19)
C11···C2^i	3.579 (2)	H8···H8^iv	2.25 (3)
C11···C7^i	3.229 (3)	H10···C9^vi	3.06 (2)
C11···C4	3.576 (3)	H11···H5^viii	2.40 (3)
C4···H11^v	2.978 (19)	H11···C4^vi	2.978 (19)
C4···H5^vi	2.985 (19)	H11···C5^vi	3.025 (19)
C5···H11^v	3.025 (19)
C2—C1—C2^i	122.43 (15)	C9—C10—C11	120.06 (19)
C1^ii—C1—C2	118.78 (9)	C6—C11—C10	120.86 (18)
C1^ii—C1—C2^i	118.78 (9)	C3—C4—H4	118.0 (9)
C1—C2—C3	120.80 (13)	C5—C4—H4	120.1 (9)
C1—C2—C6	122.92 (13)	C4—C5—H5	119.2 (11)
C3—C2—C6	115.88 (13)	C5^iii—C5—H5	120.5 (10)
C2—C3—C4	122.09 (13)	C6—C7—H7	119.3 (9)
C2—C3—C3^iii	120.01 (13)	C8—C7—H7	120.1 (9)
C3^iii—C3—C4	117.75 (13)	C7—C8—H8	119.5 (11)
C3—C4—C5	121.94 (15)	C9—C8—H8	119.9 (11)
C4—C5—C5^iii	120.30 (15)	C8—C9—H9	118.9 (12)
C2—C6—C7	122.40 (14)	C10—C9—H9	121.5 (12)
C2—C6—C11	119.04 (14)	C9—C10—H10	122.5 (12)
C7—C6—C11	118.16 (16)	C11—C10—H10	117.4 (12)
C6—C7—C8	120.65 (18)	C6—C11—H11	117.3 (11)
C7—C8—C9	120.61 (18)	C10—C11—H11	121.8 (11)
C8—C9—C10	119.65 (17)
C2^i—C1—C2—C3	−172.73 (12)	C2—C3—C3^iii—C2^iii	0.0 (2)
C2^i—C1—C2—C6	14.79 (18)	C2—C3—C3^iii—C4^iii	−175.56 (14)
C1^ii—C1—C2—C3	7.27 (16)	C4—C3—C3^iii—C2^iii	175.56 (14)
C1^ii—C1—C2—C6	−165.21 (11)	C4—C3—C3^iii—C4^iii	0.0 (2)
C1—C2—C3—C4	177.28 (13)	C3—C4—C5—C5^iii	−1.4 (3)
C1—C2—C3—C3^iii	−7.4 (2)	C4—C5—C5^iii—C4^iii	0.0 (3)
C6—C2—C3—C4	−9.7 (2)	C2—C6—C7—C8	−172.54 (17)
C6—C2—C3—C3^iii	165.63 (13)	C11—C6—C7—C8	0.1 (3)
C1—C2—C6—C7	−109.71 (18)	C2—C6—C11—C10	173.33 (17)
C1—C2—C6—C11	77.7 (2)	C7—C6—C11—C10	0.5 (3)
C3—C2—C6—C7	77.5 (2)	C6—C7—C8—C9	−0.6 (3)
C3—C2—C6—C11	−95.10 (18)	C7—C8—C9—C10	0.6 (3)
C2—C3—C4—C5	176.86 (15)	C8—C9—C10—C11	0.0 (3)
C3^iii—C3—C4—C5	1.4 (2)	C9—C10—C11—C6	−0.5 (3)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) −x+1/2, −y−1/2, −z; (v) x, y−1/2, −z+1/2; (vi) x, y+1/2, −z+1/2; (vii) x, y−1, z; (viii) x, y+1, z.

(275K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 3697 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.259 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 3697 reflections
a = 26.938 (5) Å	θ = 2.8–27.2°
b = 7.211 (1) Å	µ = 0.07 mm^−1
c = 14.461 (3) Å	T = 275 K
V = 2809.1 (9) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1466 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	1036 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.050
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.2°
phi and ω scans	h = −33→28
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −9→9
Tmin = 0.948, Tmax = 0.996	l = −18→18
10370 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	All H-atom parameters refined
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0656P)^2 + 0.4032P] where P = (Fo^2 + 2Fc^2)/3
1466 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02714 (7)	0.00000	0.00000	0.0294 (6)
C2	0.05290 (5)	−0.14318 (18)	0.04901 (9)	0.0301 (4)
C3	0.02661 (5)	−0.29299 (18)	0.08757 (9)	0.0310 (4)
C4	0.05169 (7)	−0.4439 (2)	0.13369 (10)	0.0387 (5)
C5	0.02612 (7)	−0.5841 (2)	0.17468 (11)	0.0433 (5)
C6	0.10704 (6)	−0.13275 (19)	0.07255 (10)	0.0329 (4)
C7	0.14248 (6)	−0.2446 (2)	0.03009 (12)	0.0425 (6)
C8	0.19109 (7)	−0.2464 (3)	0.06060 (15)	0.0560 (7)
C9	0.20544 (8)	−0.1361 (3)	0.13363 (15)	0.0626 (8)
C10	0.17115 (8)	−0.0238 (3)	0.17662 (14)	0.0599 (7)
C11	0.12231 (7)	−0.0226 (2)	0.14648 (11)	0.0449 (6)
H4	0.0890 (7)	−0.441 (2)	0.1366 (12)	0.053 (5)*
H5	0.0450 (6)	−0.684 (2)	0.2061 (12)	0.053 (5)*
H7	0.1322 (6)	−0.324 (2)	−0.0219 (12)	0.048 (5)*
H8	0.2160 (7)	−0.324 (3)	0.0268 (14)	0.078 (6)*
H9	0.2404 (9)	−0.138 (3)	0.1536 (15)	0.083 (7)*
H10	0.1794 (8)	0.057 (3)	0.2296 (16)	0.085 (7)*
H11	0.0964 (7)	0.050 (2)	0.1780 (13)	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0327 (11)	0.0304 (10)	0.0251 (9)	0.0000	0.0000	−0.0019 (8)
C2	0.0346 (9)	0.0310 (7)	0.0248 (7)	0.0035 (6)	0.0017 (6)	−0.0013 (6)
C3	0.0402 (8)	0.0297 (7)	0.0230 (7)	0.0023 (6)	0.0009 (6)	−0.0012 (5)
C4	0.0454 (11)	0.0365 (8)	0.0343 (8)	0.0069 (7)	0.0020 (7)	0.0043 (7)
C5	0.0584 (11)	0.0337 (8)	0.0379 (9)	0.0075 (7)	0.0014 (8)	0.0080 (7)
C6	0.0340 (9)	0.0351 (7)	0.0295 (7)	0.0033 (6)	−0.0003 (6)	0.0063 (6)
C7	0.0391 (10)	0.0411 (9)	0.0473 (10)	0.0035 (8)	0.0062 (8)	0.0020 (8)
C8	0.0383 (11)	0.0596 (11)	0.0700 (13)	0.0077 (9)	0.0104 (9)	0.0108 (10)
C9	0.0377 (12)	0.0814 (14)	0.0687 (14)	−0.0016 (10)	−0.0074 (10)	0.0196 (12)
C10	0.0566 (13)	0.0780 (13)	0.0452 (11)	−0.0076 (11)	−0.0159 (9)	0.0001 (10)
C11	0.0442 (11)	0.0551 (10)	0.0354 (9)	0.0028 (8)	−0.0015 (8)	−0.0026 (8)

Geometric parameters (Å, º)

C1—C2	1.4317 (16)	C7—C8	1.382 (3)
C1—C2^i	1.4317 (16)	C8—C9	1.378 (3)
C1—C1^ii	1.462 (3)	C9—C10	1.377 (3)
C2—C3	1.4069 (19)	C10—C11	1.386 (3)
C2—C6	1.500 (2)	C4—H4	1.006 (19)
C3—C4	1.444 (2)	C5—H5	0.992 (16)
C3—C3^iii	1.4336 (19)	C7—H7	0.985 (16)
C4—C5	1.359 (2)	C8—H8	1.00 (2)
C5—C5^iii	1.407 (3)	C9—H9	0.99 (2)
C6—C7	1.393 (2)	C10—H10	0.99 (2)
C6—C11	1.394 (2)	C11—H11	0.984 (18)
C2···C11^i	3.594 (2)	C6···H4	2.457 (15)
C4···C7	3.208 (2)	C7···H4	2.540 (17)
C4···C11	3.589 (2)	C8···H8^vi	2.849 (19)
C6···C11^i	3.385 (2)	C9···H10^iv	3.05 (2)
C6···C6^i	2.841 (2)	C11···H7^i	3.092 (16)
C6···C7^i	3.243 (2)	H4···C6	2.457 (15)
C7···C4	3.208 (2)	H4···C7	2.540 (17)
C7···C6^i	3.243 (2)	H5···H11^vii	2.40 (2)
C7···C11^i	3.245 (2)	H5···C4^iv	2.985 (16)
C11···C7^i	3.245 (2)	H7···C11^i	3.092 (16)
C11···C6^i	3.385 (2)	H8···C8^vi	2.849 (19)
C11···C2^i	3.594 (2)	H8···H8^vi	2.26 (3)
C11···C4	3.589 (2)	H10···C9^v	3.05 (2)
C4···H11^iv	2.978 (19)	H11···H5^viii	2.40 (2)
C4···H5^v	2.985 (16)	H11···C4^v	2.978 (19)
C5···H11^iv	3.010 (19)	H11···C5^v	3.010 (19)
C2—C1—C2^i	122.02 (15)	C9—C10—C11	119.90 (19)
C1^ii—C1—C2	118.99 (8)	C6—C11—C10	121.18 (16)
C1^ii—C1—C2^i	118.99 (8)	C3—C4—H4	118.1 (9)
C1—C2—C3	120.39 (13)	C5—C4—H4	120.2 (9)
C1—C2—C6	123.20 (12)	C4—C5—H5	118.7 (9)
C3—C2—C6	115.98 (12)	C5^iii—C5—H5	120.8 (9)
C2—C3—C4	121.75 (13)	C6—C7—H7	118.7 (9)
C2—C3—C3^iii	120.22 (12)	C8—C7—H7	120.3 (9)
C3^iii—C3—C4	117.89 (13)	C7—C8—H8	119.0 (11)
C3—C4—C5	121.65 (16)	C9—C8—H8	120.6 (11)
C4—C5—C5^iii	120.45 (15)	C8—C9—H9	119.0 (13)
C2—C6—C7	122.53 (13)	C10—C9—H9	121.1 (13)
C2—C6—C11	119.32 (14)	C9—C10—H10	123.1 (13)
C7—C6—C11	117.77 (15)	C11—C10—H10	117.0 (13)
C6—C7—C8	120.95 (16)	C6—C11—H11	116.7 (11)
C7—C8—C9	120.35 (18)	C10—C11—H11	122.1 (11)
C8—C9—C10	119.8 (2)
C2^i—C1—C2—C3	−172.82 (11)	C2—C3—C3^iii—C2^iii	0.00 (19)
C2^i—C1—C2—C6	14.93 (15)	C2—C3—C3^iii—C4^iii	−175.80 (12)
C1^ii—C1—C2—C3	7.18 (14)	C4—C3—C3^iii—C2^iii	175.80 (12)
C1^ii—C1—C2—C6	−165.07 (9)	C4—C3—C3^iii—C4^iii	0.00 (19)
C1—C2—C3—C4	177.10 (11)	C3—C4—C5—C5^iii	−1.2 (2)
C1—C2—C3—C3^iii	−7.27 (18)	C4—C5—C5^iii—C4^iii	0.0 (2)
C6—C2—C3—C4	−10.11 (19)	C2—C6—C7—C8	−172.64 (16)
C6—C2—C3—C3^iii	165.52 (12)	C11—C6—C7—C8	0.2 (2)
C1—C2—C6—C7	−109.65 (15)	C2—C6—C11—C10	173.26 (15)
C1—C2—C6—C11	77.62 (17)	C7—C6—C11—C10	0.2 (2)
C3—C2—C6—C7	77.78 (18)	C6—C7—C8—C9	−0.4 (3)
C3—C2—C6—C11	−94.94 (16)	C7—C8—C9—C10	0.2 (3)
C2—C3—C4—C5	176.86 (14)	C8—C9—C10—C11	0.2 (3)
C3^iii—C3—C4—C5	1.1 (2)	C9—C10—C11—C6	−0.4 (3)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) x, y−1/2, −z+1/2; (v) x, y+1/2, −z+1/2; (vi) −x+1/2, −y−1/2, −z; (vii) x, y−1, z; (viii) x, y+1, z.

(293K)

Crystal data

C42H28	The final unit cell was obtained from the xyz centroids of 1924 reflections after integration using the SAINT software package (Bruker, 2000).
Mr = 532.68	Dx = 1.269 Mg m^−3
Orthorhombic, Cmca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2bc 2	Cell parameters from 1924 reflections
a = 26.86 (1) Å	θ = 2.8–23.4°
b = 7.193 (3) Å	µ = 0.07 mm^−1
c = 14.433 (5) Å	T = 293 K
V = 2788.5 (18) Å^3	Platelet, orange
Z = 4	0.51 × 0.45 × 0.03 mm
F(000) = 1120

Data collection

Bruker Smart Apex; CCD area detector diffractometer	1451 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	938 reflections with I > 2σ(I)
Parallel mounted graphite monochromator	Rint = 0.061
Detector resolution: 4096x4096 / 62x62 (binned 512) pixels mm^-1	θmax = 26.4°, θmin = 3.0°
phi and ω scans	h = −33→33
Absorption correction: multi-scan (SADABS, Sheldrick, Bruker, 2000))	k = −8→8
Tmin = 0.949, Tmax = 0.998	l = −18→18
10259 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: difference Fourier map
wR(F^2) = 0.123	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.070P)^2 + 0.P] where P = (Fo^2 + 2Fc^2)/3
1451 reflections	(Δ/σ)max < 0.001
124 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.02705 (7)	0.00000	0.00000	0.0327 (7)
C2	0.05294 (5)	−0.1429 (2)	0.04897 (10)	0.0335 (5)
C3	0.02658 (5)	−0.2928 (2)	0.08756 (10)	0.0341 (5)
C4	0.05147 (7)	−0.4433 (2)	0.13347 (11)	0.0424 (6)
C5	0.02589 (7)	−0.5831 (2)	0.17451 (12)	0.0475 (6)
C6	0.10704 (6)	−0.1325 (2)	0.07249 (11)	0.0369 (5)
C7	0.14252 (6)	−0.2440 (2)	0.03033 (13)	0.0467 (6)
C8	0.19095 (7)	−0.2455 (3)	0.06085 (16)	0.0623 (8)
C9	0.20534 (8)	−0.1351 (3)	0.13354 (16)	0.0694 (9)
C10	0.17085 (8)	−0.0241 (3)	0.17627 (15)	0.0659 (8)
C11	0.12213 (7)	−0.0226 (3)	0.14638 (12)	0.0499 (6)
H4	0.0875 (6)	−0.441 (2)	0.1339 (10)	0.036 (4)*
H5	0.0444 (5)	−0.680 (2)	0.2050 (12)	0.055 (5)*
H7	0.1318 (6)	−0.324 (2)	−0.0213 (12)	0.053 (5)*
H8	0.2165 (7)	−0.321 (3)	0.0286 (14)	0.085 (7)*
H9	0.2409 (8)	−0.133 (2)	0.1504 (12)	0.072 (6)*
H10	0.1794 (8)	0.060 (3)	0.2267 (16)	0.091 (7)*
H11	0.0955 (6)	0.055 (2)	0.1763 (12)	0.054 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0352 (12)	0.0333 (12)	0.0296 (11)	0.0000	0.0000	−0.0037 (9)
C2	0.0370 (9)	0.0335 (8)	0.0301 (8)	0.0014 (7)	0.0015 (6)	−0.0007 (6)
C3	0.0428 (9)	0.0339 (8)	0.0255 (8)	0.0042 (7)	−0.0001 (6)	−0.0018 (6)
C4	0.0467 (11)	0.0419 (9)	0.0386 (9)	0.0070 (8)	0.0032 (8)	0.0046 (8)
C5	0.0620 (12)	0.0373 (10)	0.0432 (10)	0.0084 (8)	0.0022 (8)	0.0094 (8)
C6	0.0369 (9)	0.0400 (9)	0.0337 (8)	0.0032 (7)	0.0004 (7)	0.0054 (7)
C7	0.0420 (10)	0.0451 (10)	0.0531 (11)	0.0040 (9)	0.0070 (8)	0.0034 (9)
C8	0.0397 (11)	0.0683 (14)	0.0789 (15)	0.0072 (10)	0.0104 (10)	0.0130 (11)
C9	0.0391 (12)	0.0929 (17)	0.0763 (16)	−0.0026 (12)	−0.0072 (11)	0.0209 (14)
C10	0.0589 (14)	0.0874 (16)	0.0515 (12)	−0.0082 (12)	−0.0154 (10)	0.0006 (11)
C11	0.0484 (11)	0.0611 (12)	0.0403 (9)	0.0032 (9)	−0.0019 (8)	−0.0030 (9)

Geometric parameters (Å, º)

C1—C2	1.4282 (18)	C7—C8	1.373 (3)
C1—C2^i	1.4282 (18)	C8—C9	1.371 (3)
C1—C1^ii	1.453 (3)	C9—C10	1.370 (3)
C2—C3	1.405 (2)	C10—C11	1.378 (3)
C2—C6	1.494 (2)	C4—H4	0.968 (16)
C3—C4	1.435 (2)	C5—H5	0.963 (15)
C3—C3^iii	1.428 (2)	C7—H7	0.985 (16)
C4—C5	1.354 (2)	C8—H8	0.99 (2)
C5—C5^iii	1.391 (3)	C9—H9	0.99 (2)
C6—C7	1.386 (2)	C10—H10	0.97 (2)
C6—C11	1.388 (3)	C11—H11	1.005 (16)
C2···C11^i	3.581 (3)	C6···H4	2.447 (15)
C4···C7	3.202 (3)	C7···H4	2.535 (15)
C4···C11	3.577 (3)	C8···H8^vi	2.842 (19)
C6···C11^i	3.375 (3)	C9···H10^iv	3.06 (2)
C6···C6^i	2.831 (2)	C11···H7^i	3.089 (16)
C6···C7^i	3.232 (3)	H4···C6	2.447 (15)
C7···C4	3.202 (3)	H4···C7	2.535 (15)
C7···C6^i	3.232 (3)	H5···H11^vii	2.39 (2)
C7···C11^i	3.238 (3)	H5···C4^iv	3.010 (16)
C11···C7^i	3.238 (3)	H7···C11^i	3.089 (16)
C11···C6^i	3.375 (3)	H8···C8^vi	2.842 (19)
C11···C2^i	3.581 (3)	H8···H8^vi	2.23 (3)
C11···C4	3.577 (3)	H10···C9^v	3.06 (2)
C4···H11^iv	2.990 (17)	H11···H5^viii	2.39 (2)
C4···H5^v	3.010 (16)	H11···C4^v	2.990 (17)
C5···H11^iv	3.020 (17)	H11···C5^v	3.020 (17)
C2—C1—C2^i	121.72 (15)	C9—C10—C11	120.4 (2)
C1^ii—C1—C2	119.14 (9)	C6—C11—C10	120.89 (18)
C1^ii—C1—C2^i	119.14 (9)	C3—C4—H4	117.1 (9)
C1—C2—C3	120.21 (13)	C5—C4—H4	121.1 (9)
C1—C2—C6	123.37 (13)	C4—C5—H5	118.4 (8)
C3—C2—C6	116.01 (12)	C5^iii—C5—H5	121.1 (8)
C2—C3—C4	121.83 (13)	C6—C7—H7	118.0 (9)
C2—C3—C3^iii	120.26 (13)	C8—C7—H7	121.0 (9)
C3^iii—C3—C4	117.78 (13)	C7—C8—H8	120.6 (12)
C3—C4—C5	121.73 (16)	C9—C8—H8	118.8 (12)
C4—C5—C5^iii	120.49 (15)	C8—C9—H9	118.1 (10)
C2—C6—C7	122.68 (14)	C10—C9—H9	122.4 (10)
C2—C6—C11	119.15 (14)	C9—C10—H10	122.6 (13)
C7—C6—C11	117.78 (16)	C11—C10—H10	116.9 (13)
C6—C7—C8	120.99 (17)	C6—C11—H11	116.0 (10)
C7—C8—C9	120.52 (19)	C10—C11—H11	123.1 (10)
C8—C9—C10	119.4 (2)
C2^i—C1—C2—C3	−172.81 (12)	C2—C3—C3^iii—C2^iii	0.0 (2)
C2^i—C1—C2—C6	14.96 (17)	C2—C3—C3^iii—C4^iii	−175.85 (14)
C1^ii—C1—C2—C3	7.19 (15)	C4—C3—C3^iii—C2^iii	175.85 (14)
C1^ii—C1—C2—C6	−165.04 (10)	C4—C3—C3^iii—C4^iii	0.0 (2)
C1—C2—C3—C4	177.05 (12)	C3—C4—C5—C5^iii	−1.0 (2)
C1—C2—C3—C3^iii	−7.3 (2)	C4—C5—C5^iii—C4^iii	0.0 (3)
C6—C2—C3—C4	−10.2 (2)	C2—C6—C7—C8	−172.64 (16)
C6—C2—C3—C3^iii	165.51 (13)	C11—C6—C7—C8	0.1 (3)
C1—C2—C6—C7	−109.70 (17)	C2—C6—C11—C10	173.27 (17)
C1—C2—C6—C11	77.70 (19)	C7—C6—C11—C10	0.3 (3)
C3—C2—C6—C7	77.77 (19)	C6—C7—C8—C9	−0.5 (3)
C3—C2—C6—C11	−94.83 (18)	C7—C8—C9—C10	0.6 (3)
C2—C3—C4—C5	176.76 (15)	C8—C9—C10—C11	−0.2 (3)
C3^iii—C3—C4—C5	1.0 (2)	C9—C10—C11—C6	−0.2 (3)

Symmetry codes: (i) x, −y, −z; (ii) −x, −y, −z; (iii) −x, y, z; (iv) x, y−1/2, −z+1/2; (v) x, y+1/2, −z+1/2; (vi) −x+1/2, −y−1/2, −z; (vii) x, y−1, z; (viii) x, y+1, z.