Crystal structure of 7,15-bis­(4-tert-butyl­phen­yl)-1,9-di­methyl­hepta­zethrene

The title compound was synthesized as a derivative of hepta­zethrene bearing two methyl and two tert-butyl­phenyl substituents, respectively, at the 1,9- and 7,15-positions. Albeit remotely located, the substituents contort the hepta­zethrene plane. The phenyl substituents stand approximately perpendicular to the core plane and prevent direct inter­molecular contacts of the hepta­zethrene cores.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.131
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         22 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Note

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         13 Note
PLAT882_ALERT_1_G Missing datum for _diffrn_reflns_av_unetI/netI .     Please Check

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: CrystalStructure (Rigaku, 2016) and Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2016), OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

7,15-Bis(4-tert-butylphenyl)-1,9-dimethylheptazethrene

Crystal data

C50H44	Z = 1
Mr = 644.90	F(000) = 344.00
Triclinic, P1	Dx = 1.197 Mg m^−3
a = 8.7644 (2) Å	Cu Kα radiation, λ = 1.54187 Å
b = 9.2002 (3) Å	Cell parameters from 15939 reflections
c = 13.1212 (3) Å	θ = 3.6–68.2°
α = 105.874 (2)°	µ = 0.51 mm^−1
β = 95.080 (2)°	T = 93 K
γ = 115.249 (3)°	Block, purple
V = 894.47 (5) Å^3	0.15 × 0.08 × 0.03 mm

Data collection

Rigaku XtaLAB P200 diffractometer	2930 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 5.811 pixels mm^-1	Rint = 0.026
ω scans	θmax = 68.3°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	h = −10→10
Tmin = 0.878, Tmax = 0.985	k = −9→10
22866 measured reflections	l = −15→15
3256 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0807P)^2 + 0.1872P] where P = (Fo^2 + 2Fc^2)/3
3256 reflections	(Δ/σ)max < 0.001
230 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.77143 (15)	0.27792 (16)	0.37967 (10)	0.0282 (3)
C2	0.82438 (16)	0.19027 (16)	0.29671 (11)	0.0304 (3)
H2	0.901044	0.149216	0.316696	0.036*
C3	0.77086 (16)	0.16138 (16)	0.18882 (11)	0.0294 (3)
H3	0.802444	0.093561	0.135216	0.035*
C3A	0.66842 (15)	0.23267 (15)	0.15725 (10)	0.0270 (3)
C3A1	0.61706 (14)	0.32728 (14)	0.23942 (10)	0.0247 (3)
C4	0.61937 (16)	0.21352 (16)	0.04656 (10)	0.0299 (3)
H4	0.651358	0.147501	−0.007973	0.036*
C5	0.52627 (16)	0.28945 (16)	0.01768 (10)	0.0308 (3)
H5	0.492798	0.274895	−0.056770	0.037*
C6	0.48038 (16)	0.38832 (16)	0.09751 (10)	0.0284 (3)
H6	0.418515	0.442753	0.076400	0.034*
C6A	0.52289 (15)	0.40922 (15)	0.20719 (10)	0.0254 (3)
C7	0.47383 (15)	0.51085 (15)	0.28851 (10)	0.0253 (3)
C7A	0.49880 (15)	0.51364 (15)	0.39461 (10)	0.0255 (3)
C8	0.42937 (15)	0.59605 (15)	0.47208 (10)	0.0261 (3)
H8	0.386896	0.666232	0.452300	0.031*
C8A	0.57990 (15)	0.41936 (15)	0.42770 (10)	0.0249 (3)
C8B	0.65887 (15)	0.34037 (15)	0.35078 (10)	0.0255 (3)
C1M	0.84692 (17)	0.29973 (19)	0.49464 (11)	0.0359 (3)
H1M1	0.953456	0.288760	0.496403	0.054*
H1M2	0.762462	0.211359	0.517639	0.054*
H1M3	0.873653	0.413186	0.544212	0.054*
C1P	0.37768 (15)	0.59823 (15)	0.25632 (9)	0.0257 (3)
C2P	0.45677 (15)	0.77354 (16)	0.27639 (10)	0.0275 (3)
H2P	0.578450	0.840095	0.305958	0.033*
C3P	0.36053 (16)	0.85288 (16)	0.25386 (10)	0.0278 (3)
H3P	0.418003	0.972795	0.268045	0.033*
C4P	0.18176 (15)	0.76070 (15)	0.21096 (10)	0.0273 (3)
C5P	0.10460 (16)	0.58447 (16)	0.18943 (11)	0.0329 (3)
H5P	−0.016815	0.517320	0.158986	0.039*
C6P	0.19987 (16)	0.50500 (16)	0.21115 (11)	0.0317 (3)
H6P	0.142991	0.384575	0.194958	0.038*
C1T	0.06794 (16)	0.84316 (17)	0.19069 (11)	0.0333 (3)
C2T	−0.05461 (19)	0.8203 (2)	0.26853 (15)	0.0468 (4)
H2T1	−0.118334	0.698859	0.259859	0.070*
H2T2	−0.137001	0.861074	0.251474	0.070*
H2T3	0.013342	0.886463	0.343903	0.070*
C3T	0.17399 (17)	1.03289 (17)	0.20891 (13)	0.0401 (3)
H3T1	0.096047	1.078314	0.191671	0.060*
H3T2	0.255721	1.048167	0.161518	0.060*
H3T3	0.238494	1.094359	0.285279	0.060*
C4T	−0.04149 (19)	0.7524 (2)	0.07259 (13)	0.0465 (4)
H4T1	−0.118581	0.631892	0.061158	0.070*
H4T2	0.035486	0.759603	0.022257	0.070*
H4T3	−0.111104	0.807899	0.059085	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0275 (6)	0.0267 (6)	0.0350 (6)	0.0137 (5)	0.0094 (5)	0.0150 (5)
C2	0.0297 (6)	0.0289 (6)	0.0402 (7)	0.0168 (5)	0.0122 (5)	0.0169 (5)
C3	0.0297 (6)	0.0253 (6)	0.0382 (7)	0.0147 (5)	0.0143 (5)	0.0130 (5)
C3A	0.0256 (6)	0.0229 (6)	0.0331 (6)	0.0092 (5)	0.0105 (5)	0.0129 (5)
C3A1	0.0226 (5)	0.0204 (6)	0.0323 (6)	0.0087 (5)	0.0088 (5)	0.0124 (5)
C4	0.0327 (6)	0.0255 (6)	0.0324 (6)	0.0129 (5)	0.0126 (5)	0.0112 (5)
C5	0.0357 (7)	0.0287 (7)	0.0286 (6)	0.0132 (5)	0.0095 (5)	0.0131 (5)
C6	0.0306 (6)	0.0263 (6)	0.0319 (6)	0.0130 (5)	0.0088 (5)	0.0153 (5)
C6A	0.0239 (6)	0.0221 (6)	0.0312 (6)	0.0088 (5)	0.0082 (5)	0.0132 (5)
C7	0.0248 (6)	0.0223 (6)	0.0309 (6)	0.0106 (5)	0.0074 (5)	0.0128 (5)
C7A	0.0256 (6)	0.0229 (6)	0.0307 (6)	0.0114 (5)	0.0077 (5)	0.0131 (5)
C8	0.0272 (6)	0.0247 (6)	0.0320 (6)	0.0145 (5)	0.0078 (5)	0.0137 (5)
C8A	0.0247 (6)	0.0224 (6)	0.0290 (6)	0.0112 (5)	0.0058 (4)	0.0110 (5)
C8B	0.0239 (6)	0.0218 (6)	0.0315 (6)	0.0093 (5)	0.0078 (5)	0.0124 (5)
C1M	0.0378 (7)	0.0472 (8)	0.0390 (7)	0.0293 (6)	0.0127 (6)	0.0218 (6)
C1P	0.0294 (6)	0.0279 (6)	0.0255 (6)	0.0152 (5)	0.0097 (5)	0.0137 (5)
C2P	0.0245 (6)	0.0276 (6)	0.0327 (6)	0.0117 (5)	0.0083 (5)	0.0144 (5)
C3P	0.0283 (6)	0.0237 (6)	0.0351 (6)	0.0123 (5)	0.0098 (5)	0.0144 (5)
C4P	0.0277 (6)	0.0269 (6)	0.0315 (6)	0.0142 (5)	0.0091 (5)	0.0135 (5)
C5P	0.0256 (6)	0.0279 (7)	0.0434 (7)	0.0104 (5)	0.0041 (5)	0.0146 (6)
C6P	0.0311 (6)	0.0229 (6)	0.0409 (7)	0.0114 (5)	0.0055 (5)	0.0139 (5)
C1T	0.0261 (6)	0.0300 (7)	0.0477 (7)	0.0144 (5)	0.0088 (5)	0.0171 (6)
C2T	0.0397 (8)	0.0401 (8)	0.0768 (11)	0.0247 (7)	0.0285 (7)	0.0292 (8)
C3T	0.0315 (7)	0.0308 (7)	0.0654 (9)	0.0172 (6)	0.0110 (6)	0.0232 (7)
C4T	0.0373 (7)	0.0427 (8)	0.0607 (9)	0.0206 (7)	−0.0017 (7)	0.0205 (7)

Geometric parameters (Å, º)

C1—C2	1.4068 (18)	C1M—H1M2	0.9800
C1—C8B	1.4084 (17)	C1M—H1M3	0.9800
C1—C1M	1.5159 (17)	C1P—C2P	1.3902 (17)
C2—C3	1.3655 (18)	C1P—C6P	1.3905 (17)
C2—H2	0.9500	C2P—C3P	1.3896 (17)
C3—C3A	1.4117 (17)	C2P—H2P	0.9500
C3—H3	0.9500	C3P—C4P	1.3928 (17)
C3A—C4	1.4178 (17)	C3P—H3P	0.9500
C3A—C3A1	1.4247 (17)	C4P—C5P	1.3950 (17)
C3A1—C8B	1.4335 (17)	C4P—C1T	1.5331 (17)
C3A1—C6A	1.4394 (17)	C5P—C6P	1.3804 (17)
C4—C5	1.3689 (18)	C5P—H5P	0.9500
C4—H4	0.9500	C6P—H6P	0.9500
C5—C6	1.3970 (18)	C1T—C3T	1.5220 (18)
C5—H5	0.9500	C1T—C2T	1.5361 (19)
C6—C6A	1.3926 (17)	C1T—C4T	1.538 (2)
C6—H6	0.9500	C2T—H2T1	0.9800
C6A—C7	1.4409 (17)	C2T—H2T2	0.9800
C7—C7A	1.3813 (17)	C2T—H2T3	0.9800
C7—C1P	1.4952 (16)	C3T—H3T1	0.9800
C7A—C8	1.4353 (17)	C3T—H3T2	0.9800
C7A—C8A	1.4572 (16)	C3T—H3T3	0.9800
C8—C8A^i	1.3664 (17)	C4T—H4T1	0.9800
C8—H8	0.9500	C4T—H4T2	0.9800
C8A—C8B	1.4756 (17)	C4T—H4T3	0.9800
C1M—H1M1	0.9800
C2—C1—C8B	118.76 (11)	C1—C1M—H1M3	109.5
C2—C1—C1M	115.40 (11)	H1M1—C1M—H1M3	109.5
C8B—C1—C1M	125.82 (11)	H1M2—C1M—H1M3	109.5
C3—C2—C1	123.15 (12)	C2P—C1P—C6P	117.68 (11)
C3—C2—H2	118.4	C2P—C1P—C7	122.52 (11)
C1—C2—H2	118.4	C6P—C1P—C7	119.66 (11)
C2—C3—C3A	119.76 (12)	C3P—C2P—C1P	121.00 (11)
C2—C3—H3	120.1	C3P—C2P—H2P	119.5
C3A—C3—H3	120.1	C1P—C2P—H2P	119.5
C3—C3A—C4	121.12 (11)	C2P—C3P—C4P	121.54 (11)
C3—C3A—C3A1	118.58 (11)	C2P—C3P—H3P	119.2
C4—C3A—C3A1	120.30 (11)	C4P—C3P—H3P	119.2
C3A—C3A1—C8B	120.68 (11)	C3P—C4P—C5P	116.84 (11)
C3A—C3A1—C6A	118.01 (11)	C3P—C4P—C1T	123.67 (11)
C8B—C3A1—C6A	121.30 (11)	C5P—C4P—C1T	119.45 (11)
C5—C4—C3A	120.49 (11)	C6P—C5P—C4P	121.80 (11)
C5—C4—H4	119.8	C6P—C5P—H5P	119.1
C3A—C4—H4	119.8	C4P—C5P—H5P	119.1
C4—C5—C6	120.12 (11)	C5P—C6P—C1P	121.12 (12)
C4—C5—H5	119.9	C5P—C6P—H6P	119.4
C6—C5—H5	119.9	C1P—C6P—H6P	119.4
C6A—C6—C5	121.78 (12)	C3T—C1T—C4P	112.58 (10)
C6A—C6—H6	119.1	C3T—C1T—C2T	109.31 (12)
C5—C6—H6	119.1	C4P—C1T—C2T	108.22 (11)
C6—C6A—C3A1	119.22 (11)	C3T—C1T—C4T	108.22 (11)
C6—C6A—C7	121.14 (11)	C4P—C1T—C4T	109.63 (11)
C3A1—C6A—C7	119.64 (11)	C2T—C1T—C4T	108.82 (12)
C7A—C7—C6A	120.21 (11)	C1T—C2T—H2T1	109.5
C7A—C7—C1P	119.24 (11)	C1T—C2T—H2T2	109.5
C6A—C7—C1P	120.20 (10)	H2T1—C2T—H2T2	109.5
C7—C7A—C8	120.18 (11)	C1T—C2T—H2T3	109.5
C7—C7A—C8A	121.18 (11)	H2T1—C2T—H2T3	109.5
C8—C7A—C8A	118.35 (11)	H2T2—C2T—H2T3	109.5
C8A^i—C8—C7A	124.58 (11)	C1T—C3T—H3T1	109.5
C8A^i—C8—H8	117.7	C1T—C3T—H3T2	109.5
C7A—C8—H8	117.7	H3T1—C3T—H3T2	109.5
C8^i—C8A—C7A	116.82 (11)	C1T—C3T—H3T3	109.5
C8^i—C8A—C8B	124.06 (11)	H3T1—C3T—H3T3	109.5
C7A—C8A—C8B	119.05 (11)	H3T2—C3T—H3T3	109.5
C1—C8B—C3A1	118.48 (11)	C1T—C4T—H4T1	109.5
C1—C8B—C8A	124.42 (11)	C1T—C4T—H4T2	109.5
C3A1—C8B—C8A	117.10 (11)	H4T1—C4T—H4T2	109.5
C1—C1M—H1M1	109.5	C1T—C4T—H4T3	109.5
C1—C1M—H1M2	109.5	H4T1—C4T—H4T3	109.5
H1M1—C1M—H1M2	109.5	H4T2—C4T—H4T3	109.5
C8B—C1—C2—C3	−0.49 (19)	C2—C1—C8B—C3A1	−6.23 (17)
C1M—C1—C2—C3	−179.09 (12)	C1M—C1—C8B—C3A1	172.20 (11)
C1—C2—C3—C3A	5.13 (19)	C2—C1—C8B—C8A	173.80 (11)
C2—C3—C3A—C4	176.25 (11)	C1M—C1—C8B—C8A	−7.76 (19)
C2—C3—C3A—C3A1	−2.76 (17)	C3A—C3A1—C8B—C1	8.50 (17)
C3—C3A—C3A1—C8B	−4.01 (17)	C6A—C3A1—C8B—C1	−171.30 (10)
C4—C3A—C3A1—C8B	176.97 (10)	C3A—C3A1—C8B—C8A	−171.53 (10)
C3—C3A—C3A1—C6A	175.79 (10)	C6A—C3A1—C8B—C8A	8.67 (16)
C4—C3A—C3A1—C6A	−3.22 (17)	C8^i—C8A—C8B—C1	−16.91 (19)
C3—C3A—C4—C5	−177.21 (11)	C7A—C8A—C8B—C1	166.07 (11)
C3A1—C3A—C4—C5	1.78 (18)	C8^i—C8A—C8B—C3A1	163.12 (11)
C3A—C4—C5—C6	0.71 (18)	C7A—C8A—C8B—C3A1	−13.90 (16)
C4—C5—C6—C6A	−1.71 (19)	C7A—C7—C1P—C2P	81.89 (15)
C5—C6—C6A—C3A1	0.18 (18)	C6A—C7—C1P—C2P	−104.89 (14)
C5—C6—C6A—C7	−179.66 (11)	C7A—C7—C1P—C6P	−93.64 (14)
C3A—C3A1—C6A—C6	2.25 (16)	C6A—C7—C1P—C6P	79.58 (14)
C8B—C3A1—C6A—C6	−177.94 (10)	C6P—C1P—C2P—C3P	1.16 (17)
C3A—C3A1—C6A—C7	−177.91 (10)	C7—C1P—C2P—C3P	−174.46 (10)
C8B—C3A1—C6A—C7	1.89 (17)	C1P—C2P—C3P—C4P	0.31 (18)
C6—C6A—C7—C7A	172.31 (11)	C2P—C3P—C4P—C5P	−1.40 (18)
C3A1—C6A—C7—C7A	−7.52 (17)	C2P—C3P—C4P—C1T	176.39 (11)
C6—C6A—C7—C1P	−0.83 (17)	C3P—C4P—C5P—C6P	1.05 (19)
C3A1—C6A—C7—C1P	179.33 (10)	C1T—C4P—C5P—C6P	−176.83 (12)
C6A—C7—C7A—C8	−171.72 (10)	C4P—C5P—C6P—C1P	0.4 (2)
C1P—C7—C7A—C8	1.50 (17)	C2P—C1P—C6P—C5P	−1.51 (18)
C6A—C7—C7A—C8A	2.04 (17)	C7—C1P—C6P—C5P	174.24 (11)
C1P—C7—C7A—C8A	175.25 (10)	C3P—C4P—C1T—C3T	7.25 (18)
C7—C7A—C8—C8A^i	168.00 (12)	C5P—C4P—C1T—C3T	−175.02 (12)
C8A—C7A—C8—C8A^i	−5.93 (19)	C3P—C4P—C1T—C2T	−113.67 (14)
C7—C7A—C8A—C8^i	−168.40 (12)	C5P—C4P—C1T—C2T	64.06 (15)
C8—C7A—C8A—C8^i	5.47 (18)	C3P—C4P—C1T—C4T	127.77 (13)
C7—C7A—C8A—C8B	8.83 (17)	C5P—C4P—C1T—C4T	−54.50 (15)
C8—C7A—C8A—C8B	−177.30 (10)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C1–C3/C3A/C3A1/C8B and C3A1/C3A/C4–C6/C6A rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3P—H3P···Cg1^ii	0.95	2.80	3.6278 (15)	147
C3T—H3T2···Cg2^ii	0.98	2.97	3.7929 (17)	143

Symmetry code: (ii) x, y+1, z.