Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The crystal structures of the [6]­helicenes 4,13-(1,10-deca­methyl­ene­dioxy)­hexahelicene, C36H34O2, (I), and 4,13-(1,8-octa­methyl­ene­dioxy)­hexahelicene, C34H30O2, (II), show strong steric interactions between the terminal benzene rings and the poly­methyl­ene­dioxy chains. The shortest ring A and F distances amount to 2.941 (3) and 2.902 (3) Å, respectively. The increased steric energy of the ground state is responsible for a significantly lower racemization barrier of (I) and (II) in comparison to the unsubstituted [6]­helicene.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003140/jz1383sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003140/jz1383Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003140/jz1383IIsup3.hkl
Contains datablock II

CCDC references: 146054; 146055

Computing details top

For both compounds, data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger, 1971); program(s) used to solve structure: SIR92 (Altomare, 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976).

(I) 4,13-(1',10'-Decandioxy)hexahelicen top
Crystal data top
C36H34O2Dx = 1.254 Mg m3
Mr = 498.63Melting point: 252 K
Orthorhombic, PbcaCu Kα radiation, λ = 1.54178 Å
a = 16.8803 (5) ÅCell parameters from 25 reflections
b = 16.1855 (4) Åθ = 65–74°
c = 19.3262 (6) ŵ = 0.59 mm1
V = 5280.2 (3) Å3T = 298 K
Z = 8Rectangular block, yellow
F(000) = 21280.56 × 0.53 × 0.35 mm
Data collection top
CAD4 Enraf Nonius
diffractometer
Rint = 0.000
Radiation source: rotating anodeθmax = 75.1°, θmin = 4.4°
Graphite monochromatorh = 210
ω/2θ scansk = 020
5436 measured reflectionsl = 024
5436 independent reflections3 standard reflections every 60 min
4367 reflections with I > 2σ(I) intensity decay: 5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.156Calculated w = 1/[σ2(Fo2) + ( 0.0843P)2 + 1.8869P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
5436 reflectionsΔρmax = 0.46 e Å3
368 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2l3/sin(2q)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00122 (13)
Special details top

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

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _refine_ls_R_factor_obs 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
O20.61174 (8)0.07509 (10)0.63720 (8)0.0584 (4)
O10.26831 (9)0.09229 (10)0.91560 (8)0.0605 (4)
C10.41472 (11)0.14762 (11)0.74908 (10)0.0448 (4)
H10.44710.16090.71170.050 (6)*
C20.44797 (12)0.12847 (12)0.81174 (10)0.0499 (5)
H20.50280.12960.81630.051 (6)*
C30.40169 (13)0.10730 (13)0.86910 (11)0.0524 (5)
H30.42550.09210.91060.064 (7)*
C40.32100 (12)0.10924 (12)0.86344 (10)0.0480 (4)
C4A0.28409 (11)0.13375 (11)0.80048 (10)0.0456 (4)
C50.20080 (12)0.14914 (13)0.79807 (12)0.0554 (5)
H50.16920.13730.83620.071 (7)*
C60.16819 (12)0.18089 (14)0.74037 (13)0.0587 (5)
H60.11530.19690.74120.060 (6)*
C70.17640 (13)0.22916 (14)0.61988 (12)0.0603 (6)
H70.12330.24420.62160.063 (7)*
C6A0.21227 (12)0.19072 (12)0.67817 (11)0.0511 (5)
C80.21886 (14)0.24379 (13)0.56234 (12)0.0599 (6)
H80.19650.27460.52670.078 (8)*
C8A0.29698 (13)0.21316 (12)0.55493 (10)0.0517 (5)
C90.34053 (14)0.23073 (12)0.49390 (11)0.0572 (5)
H90.31680.26090.45860.065 (7)*
C100.41557 (14)0.20445 (13)0.48642 (11)0.0566 (5)
H100.44600.22380.44970.075 (8)*
C10A0.44884 (12)0.14727 (12)0.53414 (10)0.0488 (4)
C110.52705 (13)0.11639 (13)0.52435 (11)0.0543 (5)
H110.55820.13820.48910.068 (7)*
C120.55693 (12)0.05632 (13)0.56491 (10)0.0511 (5)
H120.61010.04180.56140.061 (7)*
C12A0.50679 (11)0.01493 (11)0.61337 (9)0.0437 (4)
C130.53325 (11)0.05783 (12)0.64753 (10)0.0462 (4)
C140.48137 (12)0.10517 (13)0.68463 (11)0.0513 (5)
H140.49840.15360.70590.059 (6)*
C150.40224 (12)0.08008 (12)0.69036 (11)0.0506 (5)
H150.36670.11340.71430.057 (6)*
C160.37601 (11)0.00810 (11)0.66185 (10)0.0448 (4)
H160.32350.00770.66770.050 (6)*
C16A0.42808 (11)0.04274 (11)0.62348 (9)0.0418 (4)
C16B0.40315 (11)0.11935 (11)0.59060 (9)0.0436 (4)
C16C0.33141 (11)0.16434 (11)0.60841 (10)0.0448 (4)
C16D0.29227 (11)0.16501 (11)0.67521 (10)0.0444 (4)
C16E0.33151 (11)0.14724 (11)0.74090 (10)0.0427 (4)
C170.29292 (15)0.05357 (14)0.97916 (11)0.0607 (6)
H17A0.34810.06670.98780.069 (5)*
H17B0.26190.07571.01710.069 (5)*
C180.28301 (15)0.03873 (15)0.97689 (14)0.0688 (6)
H18A0.28640.05961.02380.093 (7)*
H18B0.23010.05080.96000.093 (7)*
C190.34227 (14)0.08622 (15)0.93245 (14)0.0678 (6)
H19A0.34950.05760.88880.071 (5)*
H19B0.32130.14070.92250.071 (5)*
C200.42203 (16)0.09480 (19)0.96851 (15)0.0782 (7)
H20A0.41460.12711.01030.108 (8)*
H20B0.43970.04020.98240.108 (8)*
C210.48731 (18)0.13487 (19)0.92578 (17)0.0869 (9)
H21A0.46470.18080.90030.117 (9)*
H21B0.52680.15720.95710.117 (9)*
C220.52777 (17)0.07877 (17)0.87573 (13)0.0715 (7)
H22A0.48930.06000.84190.099 (7)*
H22B0.54670.03060.90050.099 (7)*
C230.59770 (16)0.11826 (16)0.83735 (13)0.0689 (6)
H23A0.57830.16330.80890.084 (6)*
H23B0.63440.14120.87090.084 (6)*
C240.64128 (14)0.05703 (15)0.79187 (13)0.0634 (6)
H24A0.60270.02260.76840.074 (5)*
H24B0.67310.02140.82110.074 (5)*
C250.69474 (13)0.09652 (16)0.73789 (13)0.0651 (6)
H25A0.72700.13820.76040.071 (5)*
H25B0.73020.05460.71990.071 (5)*
C260.65194 (13)0.13602 (14)0.67803 (12)0.0577 (5)
H26A0.61380.17570.69550.067 (5)*
H26B0.68970.16540.64930.067 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0459 (8)0.0685 (9)0.0607 (9)0.0089 (7)0.0037 (6)0.0099 (7)
O10.0599 (9)0.0681 (9)0.0534 (8)0.0039 (7)0.0082 (7)0.0072 (7)
C10.0474 (10)0.0426 (9)0.0444 (9)0.0028 (8)0.0014 (8)0.0040 (8)
C20.0449 (10)0.0524 (11)0.0523 (11)0.0026 (8)0.0054 (8)0.0020 (9)
C30.0570 (12)0.0545 (11)0.0456 (10)0.0025 (9)0.0065 (9)0.0008 (9)
C40.0552 (11)0.0416 (9)0.0471 (10)0.0039 (8)0.0039 (8)0.0028 (8)
C4A0.0484 (10)0.0376 (9)0.0507 (10)0.0026 (7)0.0002 (8)0.0057 (8)
C50.0493 (11)0.0552 (12)0.0617 (12)0.0027 (9)0.0051 (9)0.0068 (10)
C60.0410 (10)0.0598 (12)0.0752 (14)0.0046 (9)0.0032 (10)0.0084 (11)
C70.0543 (12)0.0533 (12)0.0735 (15)0.0104 (9)0.0190 (11)0.0082 (10)
C6A0.0488 (11)0.0448 (10)0.0598 (12)0.0023 (8)0.0096 (9)0.0087 (9)
C80.0691 (13)0.0468 (11)0.0638 (13)0.0070 (10)0.0230 (11)0.0020 (10)
C8A0.0666 (13)0.0384 (9)0.0502 (11)0.0016 (8)0.0161 (9)0.0035 (8)
C90.0802 (15)0.0433 (10)0.0483 (11)0.0015 (10)0.0161 (10)0.0032 (9)
C100.0774 (15)0.0475 (11)0.0449 (10)0.0103 (10)0.0047 (10)0.0050 (9)
C10A0.0598 (12)0.0428 (9)0.0439 (10)0.0091 (8)0.0042 (8)0.0016 (8)
C110.0590 (12)0.0570 (12)0.0469 (10)0.0141 (10)0.0051 (9)0.0016 (9)
C120.0464 (11)0.0568 (11)0.0501 (10)0.0066 (9)0.0029 (8)0.0026 (9)
C12A0.0447 (9)0.0458 (10)0.0406 (9)0.0046 (8)0.0025 (7)0.0053 (7)
C130.0421 (9)0.0502 (10)0.0463 (10)0.0008 (8)0.0018 (8)0.0049 (8)
C140.0500 (11)0.0469 (10)0.0568 (11)0.0031 (8)0.0026 (9)0.0057 (9)
C150.0492 (10)0.0438 (10)0.0587 (12)0.0061 (8)0.0036 (9)0.0030 (9)
C160.0412 (9)0.0403 (9)0.0528 (10)0.0016 (7)0.0007 (8)0.0030 (8)
C16A0.0462 (10)0.0397 (9)0.0394 (9)0.0040 (7)0.0041 (7)0.0049 (7)
C16B0.0492 (10)0.0403 (9)0.0414 (9)0.0055 (7)0.0062 (8)0.0029 (7)
C16C0.0506 (10)0.0369 (9)0.0469 (10)0.0025 (7)0.0095 (8)0.0036 (7)
C16D0.0476 (10)0.0358 (9)0.0498 (10)0.0015 (7)0.0077 (8)0.0041 (7)
C16E0.0478 (10)0.0346 (8)0.0458 (9)0.0008 (7)0.0034 (8)0.0052 (7)
C170.0729 (15)0.0604 (13)0.0487 (11)0.0038 (11)0.0071 (10)0.0055 (10)
C180.0652 (14)0.0600 (13)0.0813 (16)0.0071 (11)0.0079 (12)0.0128 (12)
C190.0686 (15)0.0554 (13)0.0793 (16)0.0097 (11)0.0048 (12)0.0038 (11)
C200.0697 (16)0.0839 (18)0.0810 (17)0.0029 (13)0.0042 (13)0.0128 (15)
C210.0817 (18)0.0793 (18)0.100 (2)0.0131 (15)0.0008 (17)0.0224 (16)
C220.0832 (17)0.0694 (15)0.0618 (14)0.0097 (13)0.0009 (13)0.0037 (12)
C230.0754 (16)0.0705 (15)0.0606 (14)0.0079 (12)0.0069 (12)0.0032 (12)
C240.0594 (13)0.0644 (13)0.0665 (14)0.0016 (10)0.0110 (11)0.0044 (11)
C250.0470 (11)0.0760 (15)0.0722 (15)0.0024 (10)0.0063 (10)0.0042 (12)
C260.0488 (11)0.0590 (12)0.0652 (13)0.0128 (9)0.0023 (10)0.0001 (10)
Geometric parameters (Å, º) top
O2—C131.369 (2)C10A—C111.424 (3)
O2—C261.434 (3)C11—C121.347 (3)
O1—C41.372 (2)C12—C12A1.429 (3)
O1—C171.440 (3)C12A—C16A1.416 (3)
C1—C21.370 (3)C12A—C131.422 (3)
C1—C16E1.414 (3)C13—C141.367 (3)
C2—C31.399 (3)C14—C151.400 (3)
C3—C41.367 (3)C15—C161.363 (3)
C4—C4A1.424 (3)C16—C16A1.414 (3)
C4A—C16E1.419 (3)C16A—C16B1.455 (3)
C4A—C51.429 (3)C16B—C16C1.454 (3)
C5—C61.346 (3)C16C—C16D1.450 (3)
C6—C6A1.423 (3)C16D—C16E1.460 (3)
C7—C81.344 (3)C17—C181.504 (3)
C7—C6A1.422 (3)C18—C191.526 (4)
C6A—C16D1.414 (3)C19—C201.522 (4)
C8—C8A1.416 (3)C20—C211.522 (4)
C8A—C91.419 (3)C21—C221.492 (4)
C8A—C16C1.425 (3)C22—C231.534 (4)
C9—C101.344 (3)C23—C241.515 (3)
C10—C10A1.422 (3)C24—C251.520 (3)
C10A—C16B1.410 (3)C25—C261.506 (3)
C13—O2—C26121.21 (16)C14—C13—O2125.62 (18)
C4—O1—C17121.78 (17)C14—C13—C12A120.42 (18)
C2—C1—C16E120.32 (18)O2—C13—C12A113.92 (17)
C1—C2—C3121.80 (19)C13—C14—C15119.35 (18)
C4—C3—C2119.18 (19)C16—C15—C14121.72 (19)
C3—C4—O1125.63 (19)C15—C16—C16A120.50 (18)
C3—C4—C4A120.73 (18)C16—C16A—C12A118.06 (17)
O1—C4—C4A113.58 (17)C16—C16A—C16B123.02 (17)
C16E—C4A—C4119.31 (17)C12A—C16A—C16B118.80 (16)
C16E—C4A—C5120.12 (19)C10A—C16B—C16C118.56 (17)
C4—C4A—C5120.48 (18)C10A—C16B—C16A116.91 (17)
C6—C5—C4A119.7 (2)C16C—C16B—C16A124.33 (17)
C5—C6—C6A121.93 (19)C8A—C16C—C16D117.11 (17)
C8—C7—C6A120.4 (2)C8A—C16C—C16B116.46 (18)
C16D—C6A—C7120.2 (2)C16D—C16C—C16B126.42 (17)
C16D—C6A—C6120.04 (19)C6A—C16D—C16C118.24 (17)
C7—C6A—C6119.70 (19)C6A—C16D—C16E117.12 (18)
C7—C8—C8A121.2 (2)C16C—C16D—C16E124.45 (17)
C8—C8A—C9119.77 (19)C1—C16E—C4A118.06 (17)
C8—C8A—C16C120.0 (2)C1—C16E—C16D123.16 (17)
C9—C8A—C16C120.2 (2)C4A—C16E—C16D118.67 (17)
C10—C9—C8A120.95 (19)O1—C17—C18112.0 (2)
C9—C10—C10A120.6 (2)C17—C18—C19116.3 (2)
C16B—C10A—C10119.6 (2)C20—C19—C18111.6 (2)
C16B—C10A—C11119.82 (18)C21—C20—C19115.5 (3)
C10—C10A—C11120.54 (19)C22—C21—C20115.1 (2)
C12—C11—C10A121.54 (19)C21—C22—C23114.3 (2)
C11—C12—C12A119.87 (19)C24—C23—C22112.4 (2)
C16A—C12A—C13119.60 (17)C23—C24—C25114.3 (2)
C16A—C12A—C12119.79 (18)C26—C25—C24114.88 (19)
C13—C12A—C12120.43 (18)O2—C26—C25110.96 (19)
C16E—C1—C2—C30.6 (3)C10—C10A—C16B—C16C15.1 (3)
C1—C2—C3—C42.9 (3)C11—C10A—C16B—C16C166.58 (17)
C2—C3—C4—O1178.16 (18)C10—C10A—C16B—C16A159.91 (17)
C2—C3—C4—C4A1.0 (3)C11—C10A—C16B—C16A18.4 (3)
C17—O1—C4—C313.2 (3)C16—C16A—C16B—C10A156.43 (17)
C17—O1—C4—C4A169.46 (17)C12A—C16A—C16B—C10A19.7 (2)
C3—C4—C4A—C16E7.1 (3)C16—C16A—C16B—C16C18.2 (3)
O1—C4—C4A—C16E175.42 (16)C12A—C16A—C16B—C16C165.68 (16)
C3—C4—C4A—C5169.40 (19)C8—C8A—C16C—C16D14.8 (3)
O1—C4—C4A—C58.0 (3)C9—C8A—C16C—C16D165.69 (17)
C16E—C4A—C5—C63.8 (3)C8—C8A—C16C—C16B165.88 (17)
C4—C4A—C5—C6172.74 (19)C9—C8A—C16C—C16B13.6 (3)
C4A—C5—C6—C6A7.7 (3)C10A—C16B—C16C—C8A22.1 (2)
C8—C7—C6A—C16D2.2 (3)C16A—C16B—C16C—C8A152.50 (17)
C8—C7—C6A—C6175.6 (2)C10A—C16B—C16C—C16D157.18 (17)
C5—C6—C6A—C16D1.5 (3)C16A—C16B—C16C—C16D28.2 (3)
C5—C6—C6A—C7176.2 (2)C7—C6A—C16D—C16C11.5 (3)
C6A—C7—C8—C8A7.4 (3)C6—C6A—C16D—C16C170.74 (17)
C7—C8—C8A—C9179.13 (19)C7—C6A—C16D—C16E163.72 (18)
C7—C8—C8A—C16C1.3 (3)C6—C6A—C16D—C16E14.0 (3)
C8—C8A—C9—C10178.04 (19)C8A—C16C—C16D—C6A19.6 (3)
C16C—C8A—C9—C102.4 (3)C16B—C16C—C16D—C6A161.19 (17)
C8A—C9—C10—C10A10.3 (3)C8A—C16C—C16D—C16E155.30 (17)
C9—C10—C10A—C16B1.4 (3)C16B—C16C—C16D—C16E24.0 (3)
C9—C10—C10A—C11176.97 (19)C2—C1—C16E—C4A5.4 (3)
C16B—C10A—C11—C124.9 (3)C2—C1—C16E—C16D178.42 (17)
C10—C10A—C11—C12173.45 (19)C4—C4A—C16E—C19.2 (3)
C10A—C11—C12—C12A7.9 (3)C5—C4A—C16E—C1167.36 (18)
C11—C12—C12A—C16A6.3 (3)C4—C4A—C16E—C16D174.51 (16)
C11—C12—C12A—C13168.75 (18)C5—C4A—C16E—C16D8.9 (3)
C26—O2—C13—C1414.6 (3)C6A—C16D—C16E—C1158.60 (18)
C26—O2—C13—C12A167.64 (18)C16C—C16D—C16E—C116.3 (3)
C16A—C12A—C13—C146.2 (3)C6A—C16D—C16E—C4A17.5 (2)
C12—C12A—C13—C14168.89 (19)C16C—C16D—C16E—C4A167.58 (17)
C16A—C12A—C13—O2175.89 (16)C4—O1—C17—C1893.8 (2)
C12—C12A—C13—O29.0 (3)O1—C17—C18—C1973.3 (3)
O2—C13—C14—C15179.46 (19)C17—C18—C19—C2077.2 (3)
C12A—C13—C14—C151.8 (3)C18—C19—C20—C21175.0 (2)
C13—C14—C15—C162.3 (3)C19—C20—C21—C2280.9 (3)
C14—C15—C16—C16A1.9 (3)C20—C21—C22—C23175.3 (2)
C15—C16—C16A—C12A2.5 (3)C21—C22—C23—C24175.0 (2)
C15—C16—C16A—C16B178.66 (17)C22—C23—C24—C25163.3 (2)
C13—C12A—C16A—C166.5 (3)C23—C24—C25—C2673.3 (3)
C12—C12A—C16A—C16168.66 (17)C13—O2—C26—C2595.8 (2)
C13—C12A—C16A—C16B177.24 (16)C24—C25—C26—O266.1 (3)
C12—C12A—C16A—C16B7.6 (2)
(II) 4,13-(1,8 octandioxy)-hexahelicen top
Crystal data top
C34H30O2Dx = 1.286 Mg m3
Mr = 470.58Melting point: 243 K
Orthorhombic, Pna21Cu Kα radiation, λ = 1.54178 Å
a = 18.1447 (4) ÅCell parameters from 25 reflections
b = 12.3799 (3) Åθ = 66–74°
c = 10.8228 (3) ŵ = 0.61 mm1
V = 2431.12 (10) Å3T = 298 K
Z = 4Rectangular block, yellow
F(000) = 10000.41 × 0.41 × 0.32 mm
Data collection top
CAD4 Enraf Nonius
diffractometer
Rint = 0.000
Radiation source: rotating anodeθmax = 75.0°, θmin = 4.3°
Graphite monochromatorh = 2222
ω/2θ scansk = 1515
4962 measured reflectionsl = 1313
4962 independent reflections3 standard reflections every 60 min
4855 reflections with I > 2σ(I) intensity decay: 5%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039Calculated w = 1/[σ2(Fo2) + ( 0.0742P)2 + 0.2614P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.111(Δ/σ)max = 0.001
S = 1.07Δρmax = 0.34 e Å3
4962 reflectionsΔρmin = 0.18 e Å3
348 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2l3/sin(2q)]-1/4
1 restraintExtinction coefficient: 0.0050 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (27)
Special details top

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

Refinement. Refinement on F2 for ALL reflections except for 0 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _refine_ls_R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.93523 (7)0.06201 (10)0.21811 (15)0.0575 (4)
O20.65710 (7)0.44666 (10)0.29553 (15)0.0579 (3)
C10.75394 (9)0.04490 (13)0.41749 (15)0.0397 (3)
H10.71280.07170.45870.041 (5)*
C20.82178 (9)0.08815 (14)0.44095 (16)0.0437 (3)
H20.82640.14160.50080.042 (5)*
C30.88432 (9)0.05371 (14)0.37685 (17)0.0465 (4)
H30.92990.08540.39230.051 (5)*
C40.87797 (9)0.02715 (12)0.29106 (17)0.0435 (3)
C4A0.80975 (9)0.08165 (12)0.27443 (15)0.0411 (3)
C50.80609 (11)0.18125 (14)0.20703 (17)0.0501 (4)
H50.84740.20630.16490.043 (5)*
C60.74299 (12)0.23865 (13)0.20462 (19)0.0546 (4)
H60.74310.30720.16940.069 (7)*
C6A0.67602 (10)0.19685 (14)0.25484 (16)0.0480 (4)
C70.61018 (12)0.25995 (16)0.25756 (19)0.0582 (5)
H70.60950.32730.21950.081 (8)*
C80.54900 (12)0.22331 (17)0.31458 (19)0.0599 (5)
H80.50870.26900.32360.072 (7)*
C8A0.54502 (10)0.11591 (15)0.36120 (18)0.0518 (4)
C90.48470 (10)0.07768 (19)0.4338 (2)0.0622 (5)
H90.44430.12240.44740.081 (8)*
C100.48544 (10)0.02253 (19)0.4831 (2)0.0602 (5)
H100.45120.04090.54340.071 (7)*
C10A0.53821 (9)0.10030 (16)0.44330 (16)0.0493 (4)
C110.53627 (10)0.20997 (17)0.48409 (17)0.0538 (4)
H110.50440.22960.54760.060 (6)*
C120.58021 (9)0.28623 (16)0.43163 (18)0.0504 (4)
H120.58240.35520.46550.060 (6)*
C12A0.62313 (8)0.26065 (13)0.32438 (16)0.0414 (3)
C130.65593 (9)0.34202 (13)0.25103 (17)0.0456 (4)
C140.68265 (10)0.31985 (15)0.13612 (18)0.0497 (4)
H140.69920.37540.08540.051 (5)*
C150.68502 (9)0.21235 (14)0.09500 (16)0.0452 (4)
H150.70330.19700.01670.060 (6)*
C160.66066 (8)0.12967 (13)0.16893 (15)0.0402 (3)
H160.66570.05850.14270.039 (5)*
C16A0.62805 (8)0.15183 (12)0.28441 (14)0.0376 (3)
C16B0.59276 (8)0.06875 (13)0.35795 (15)0.0419 (3)
C16C0.60533 (9)0.04521 (14)0.34002 (15)0.0428 (3)
C16D0.67517 (9)0.09163 (13)0.30543 (15)0.0411 (3)
C16E0.74542 (8)0.04008 (12)0.33142 (14)0.0378 (3)
C170.98596 (9)0.01887 (15)0.1737 (2)0.0535 (4)
H1711.02970.01670.14200.067 (5)*
H1721.00090.06420.24240.067 (5)*
C180.95384 (13)0.08957 (17)0.07326 (19)0.0592 (5)
H1810.92780.04300.01600.092 (7)*
H1820.99460.12160.02830.092 (7)*
C190.90134 (11)0.18107 (15)0.11024 (18)0.0517 (4)
H1910.87950.21140.03620.053 (4)*
H1920.86180.15140.16020.053 (4)*
C200.93925 (10)0.27097 (15)0.1823 (2)0.0532 (4)
H2010.95290.24320.26290.070 (5)*
H2020.98440.29020.13960.070 (5)*
C210.89364 (12)0.37301 (15)0.2005 (2)0.0589 (5)
H2110.92670.43170.22180.062 (5)*
H2120.87050.39130.12240.062 (5)*
C220.83492 (11)0.36593 (15)0.2975 (2)0.0591 (5)
H2210.85720.35070.37700.058 (4)*
H2220.80130.30750.27780.058 (4)*
C230.79186 (12)0.47374 (16)0.3043 (3)0.0729 (7)
H2310.82320.52670.34410.130 (10)*
H2320.78340.49850.22040.130 (10)*
C240.72014 (12)0.47311 (17)0.3695 (3)0.0708 (6)
H2410.72310.42170.43700.079 (6)*
H2420.71240.54400.40540.079 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0492 (7)0.0460 (6)0.0774 (9)0.0061 (5)0.0175 (7)0.0034 (6)
O20.0490 (6)0.0421 (6)0.0827 (10)0.0028 (5)0.0052 (7)0.0106 (6)
C10.0415 (8)0.0413 (7)0.0363 (7)0.0021 (6)0.0017 (6)0.0010 (6)
C20.0482 (8)0.0433 (8)0.0398 (8)0.0018 (6)0.0047 (7)0.0055 (6)
C30.0400 (8)0.0473 (8)0.0523 (9)0.0050 (6)0.0038 (7)0.0001 (7)
C40.0417 (8)0.0397 (7)0.0491 (8)0.0059 (6)0.0028 (7)0.0022 (7)
C4A0.0473 (8)0.0362 (7)0.0399 (8)0.0022 (6)0.0016 (7)0.0018 (6)
C50.0596 (10)0.0400 (8)0.0506 (9)0.0041 (7)0.0028 (8)0.0062 (7)
C60.0745 (12)0.0355 (7)0.0539 (10)0.0010 (7)0.0056 (9)0.0082 (7)
C6A0.0590 (10)0.0409 (8)0.0440 (8)0.0105 (7)0.0091 (7)0.0027 (6)
C70.0729 (12)0.0473 (9)0.0544 (10)0.0203 (9)0.0144 (9)0.0018 (8)
C80.0602 (11)0.0577 (10)0.0616 (11)0.0278 (9)0.0164 (9)0.0163 (9)
C8A0.0445 (9)0.0590 (10)0.0519 (9)0.0130 (8)0.0087 (7)0.0170 (8)
C90.0393 (9)0.0777 (14)0.0696 (12)0.0148 (9)0.0036 (9)0.0271 (11)
C100.0381 (9)0.0847 (14)0.0579 (11)0.0021 (9)0.0074 (8)0.0213 (10)
C10A0.0378 (8)0.0673 (11)0.0428 (8)0.0041 (7)0.0000 (7)0.0104 (8)
C110.0441 (9)0.0721 (12)0.0451 (9)0.0104 (8)0.0040 (7)0.0029 (8)
C120.0425 (8)0.0574 (10)0.0513 (9)0.0077 (7)0.0042 (7)0.0094 (8)
C12A0.0325 (7)0.0455 (8)0.0461 (8)0.0032 (6)0.0066 (6)0.0030 (6)
C130.0386 (7)0.0398 (8)0.0583 (10)0.0002 (6)0.0051 (7)0.0029 (7)
C140.0506 (10)0.0429 (8)0.0555 (10)0.0090 (7)0.0018 (7)0.0062 (7)
C150.0470 (9)0.0486 (9)0.0400 (8)0.0078 (7)0.0002 (7)0.0005 (7)
C160.0388 (7)0.0407 (7)0.0410 (7)0.0048 (6)0.0030 (6)0.0034 (6)
C16A0.0312 (6)0.0423 (7)0.0394 (7)0.0015 (5)0.0044 (6)0.0006 (6)
C16B0.0339 (7)0.0492 (8)0.0426 (8)0.0024 (6)0.0039 (6)0.0046 (7)
C16C0.0407 (8)0.0477 (8)0.0400 (7)0.0086 (6)0.0034 (6)0.0076 (6)
C16D0.0454 (8)0.0399 (7)0.0381 (7)0.0054 (6)0.0051 (6)0.0049 (6)
C16E0.0407 (8)0.0364 (7)0.0361 (7)0.0004 (6)0.0032 (6)0.0040 (5)
C170.0384 (9)0.0533 (10)0.0688 (12)0.0062 (7)0.0084 (8)0.0011 (9)
C180.0686 (12)0.0554 (11)0.0536 (10)0.0084 (9)0.0063 (9)0.0011 (8)
C190.0542 (10)0.0518 (9)0.0491 (9)0.0061 (8)0.0056 (8)0.0028 (8)
C200.0493 (9)0.0504 (9)0.0597 (10)0.0016 (7)0.0030 (8)0.0023 (8)
C210.0654 (11)0.0445 (9)0.0669 (12)0.0019 (8)0.0108 (10)0.0022 (9)
C220.0484 (9)0.0460 (9)0.0827 (14)0.0006 (7)0.0065 (9)0.0102 (9)
C230.0560 (11)0.0451 (10)0.118 (2)0.0010 (8)0.0014 (13)0.0146 (11)
C240.0589 (12)0.0510 (10)0.1026 (18)0.0013 (9)0.0069 (11)0.0259 (12)
Geometric parameters (Å, º) top
O1—C41.374 (2)C10A—C16B1.409 (2)
O1—C171.443 (2)C10A—C111.428 (3)
O2—C131.382 (2)C11—C121.360 (3)
O2—C241.434 (3)C12—C12A1.433 (2)
C1—C21.366 (2)C12A—C131.414 (2)
C1—C16E1.414 (2)C12A—C16A1.418 (2)
C2—C31.397 (2)C13—C141.363 (3)
C3—C41.370 (2)C14—C151.404 (3)
C4—C4A1.421 (2)C15—C161.372 (2)
C4A—C16E1.417 (2)C16—C16A1.410 (2)
C4A—C51.434 (2)C16A—C16B1.450 (2)
C5—C61.348 (3)C16B—C16C1.442 (2)
C6—C6A1.428 (3)C16C—C16D1.441 (2)
C6A—C16D1.413 (2)C16D—C16E1.453 (2)
C6A—C71.428 (3)C17—C181.512 (3)
C7—C81.349 (3)C18—C191.533 (3)
C8—C8A1.424 (3)C19—C201.523 (3)
C8A—C16C1.420 (2)C20—C211.523 (3)
C8A—C91.428 (3)C21—C221.499 (3)
C9—C101.350 (3)C22—C231.548 (3)
C10—C10A1.424 (3)C23—C241.480 (3)
C4—O1—C17117.12 (13)C16A—C12A—C12119.42 (16)
C13—O2—C24114.87 (14)C14—C13—O2120.09 (17)
C2—C1—C16E120.84 (15)C14—C13—C12A121.24 (16)
C1—C2—C3121.34 (16)O2—C13—C12A118.59 (16)
C4—C3—C2119.42 (16)C13—C14—C15119.41 (16)
C3—C4—O1123.72 (16)C16—C15—C14120.82 (16)
C3—C4—C4A120.39 (15)C15—C16—C16A120.47 (15)
O1—C4—C4A115.88 (15)C16—C16A—C12A118.80 (14)
C16E—C4A—C4119.34 (14)C16—C16A—C16B122.29 (14)
C16E—C4A—C5119.71 (15)C12A—C16A—C16B118.61 (14)
C4—C4A—C5120.85 (15)C10A—C16B—C16C118.06 (15)
C6—C5—C4A120.16 (17)C10A—C16B—C16A118.27 (15)
C5—C6—C6A121.63 (16)C16C—C16B—C16A123.39 (15)
C16D—C6A—C7119.16 (18)C8A—C16C—C16D118.28 (16)
C16D—C6A—C6119.39 (15)C8A—C16C—C16B117.35 (16)
C7—C6A—C6121.43 (18)C16D—C16C—C16B124.35 (14)
C8—C7—C6A120.94 (19)C6A—C16D—C16C118.55 (15)
C7—C8—C8A121.20 (17)C6A—C16D—C16E118.05 (15)
C16C—C8A—C8118.64 (18)C16C—C16D—C16E123.10 (14)
C16C—C8A—C9118.37 (18)C1—C16E—C4A117.85 (13)
C8—C8A—C9122.91 (17)C1—C16E—C16D123.39 (14)
C10—C9—C8A120.94 (17)C4A—C16E—C16D118.61 (14)
C9—C10—C10A120.56 (19)O1—C17—C18113.29 (16)
C16B—C10A—C10118.87 (19)C17—C18—C19118.65 (17)
C16B—C10A—C11118.91 (16)C20—C19—C18113.13 (16)
C10—C10A—C11122.19 (18)C21—C20—C19115.26 (16)
C12—C11—C10A121.10 (17)C22—C21—C20115.35 (17)
C11—C12—C12A120.22 (17)C21—C22—C23109.97 (19)
C13—C12A—C16A118.63 (15)C24—C23—C22117.5 (2)
C13—C12A—C12121.74 (16)O2—C24—C23115.9 (2)
C16E—C1—C2—C33.1 (3)C12—C12A—C16A—C16B3.5 (2)
C1—C2—C3—C41.8 (3)C10—C10A—C16B—C16C16.4 (2)
C2—C3—C4—O1175.90 (16)C11—C10A—C16B—C16C165.55 (15)
C2—C3—C4—C4A5.1 (3)C10—C10A—C16B—C16A157.72 (16)
C17—O1—C4—C337.4 (3)C11—C10A—C16B—C16A20.4 (2)
C17—O1—C4—C4A143.53 (16)C16—C16A—C16B—C10A155.39 (15)
C3—C4—C4A—C16E10.7 (2)C12A—C16A—C16B—C10A18.2 (2)
O1—C4—C4A—C16E170.23 (14)C16—C16A—C16B—C16C18.4 (2)
C3—C4—C4A—C5165.59 (16)C12A—C16A—C16B—C16C168.01 (14)
O1—C4—C4A—C513.5 (2)C8—C8A—C16C—C16D17.7 (2)
C16E—C4A—C5—C64.3 (3)C9—C8A—C16C—C16D159.12 (16)
C4—C4A—C5—C6171.96 (18)C8—C8A—C16C—C16B163.88 (16)
C4A—C5—C6—C6A7.9 (3)C9—C8A—C16C—C16B19.3 (2)
C5—C6—C6A—C16D1.7 (3)C10A—C16B—C16C—C8A27.9 (2)
C5—C6—C6A—C7176.88 (18)C16A—C16B—C16C—C8A145.83 (16)
C16D—C6A—C7—C84.3 (3)C10A—C16B—C16C—C16D150.36 (16)
C6—C6A—C7—C8174.28 (18)C16A—C16B—C16C—C16D35.9 (2)
C6A—C7—C8—C8A7.5 (3)C7—C6A—C16D—C16C9.8 (2)
C7—C8—C8A—C16C3.8 (3)C6—C6A—C16D—C16C171.57 (16)
C7—C8—C8A—C9172.92 (19)C7—C6A—C16D—C16E164.12 (16)
C16C—C8A—C9—C101.2 (3)C6—C6A—C16D—C16E14.5 (2)
C8—C8A—C9—C10175.55 (19)C8A—C16C—C16D—C6A20.7 (2)
C8A—C9—C10—C10A13.3 (3)C16B—C16C—C16D—C6A161.05 (16)
C9—C10—C10A—C16B4.3 (3)C8A—C16C—C16D—C16E152.92 (16)
C9—C10—C10A—C11173.73 (18)C16B—C16C—C16D—C16E25.4 (2)
C16B—C10A—C11—C127.7 (3)C2—C1—C16E—C4A2.6 (2)
C10—C10A—C11—C12170.30 (18)C2—C1—C16E—C16D177.99 (15)
C10A—C11—C12—C12A7.4 (3)C4—C4A—C16E—C19.2 (2)
C11—C12—C12A—C13165.37 (17)C5—C4A—C16E—C1167.08 (15)
C11—C12—C12A—C16A9.3 (2)C4—C4A—C16E—C16D175.09 (14)
C24—O2—C13—C1494.4 (2)C5—C4A—C16E—C16D8.6 (2)
C24—O2—C13—C12A88.8 (2)C6A—C16D—C16E—C1157.62 (15)
C16A—C12A—C13—C149.2 (2)C16C—C16D—C16E—C116.0 (2)
C12—C12A—C13—C14165.53 (16)C6A—C16D—C16E—C4A17.8 (2)
C16A—C12A—C13—O2174.10 (13)C16C—C16D—C16E—C4A168.59 (15)
C12—C12A—C13—O211.1 (2)C4—O1—C17—C1872.9 (2)
O2—C13—C14—C15176.34 (16)O1—C17—C18—C1978.5 (2)
C12A—C13—C14—C157.0 (3)C17—C18—C19—C2067.6 (2)
C13—C14—C15—C160.1 (3)C18—C19—C20—C21169.03 (18)
C14—C15—C16—C16A4.4 (2)C19—C20—C21—C2276.7 (2)
C15—C16—C16A—C12A2.1 (2)C20—C21—C22—C23178.75 (18)
C15—C16—C16A—C16B171.57 (15)C21—C22—C23—C24164.1 (2)
C13—C12A—C16A—C164.6 (2)C13—O2—C24—C2366.0 (3)
C12—C12A—C16A—C16170.31 (14)C22—C23—C24—O288.4 (3)
C13—C12A—C16A—C16B178.41 (14)
Angles (°) between the averaged planes (least squares) of the benzene rings A-F and torsion angles α and β of the hexahelicenophanes (I) and (II) top
ABBCCDDEEFAF
[6]helicene9.815.214.415.211.558.5
(1)11.5 (1)11.1 (1)11.2 (1)14.5 (1)12.7 (1)45.2 (1)
(2)13.2 (1)11.0 (1)15.4 (1)17.2 (1)15.3 (1)57.5 (1)
α1β1β2α2
[6]helicene11.230.030.315.2
(1)-16.3 (3)-24.0 (3)-28.2 (3)-18.2 (3)
(2)16.0 (2)25.4 (2)35.9 (2)18.4 (2)
Non-bonding interactions between the benzene rings A, F and C14 and the corresponding chain segments: C-C distances in Å top
(1)(2)
C3···C172.941 (3)2.902 (3)
C3···C183.733 (3)3.547 (3)
C3···C193.509 (3)3.302 (3)
C1···C163.102 (3)3.347 (2)
C2···C154.182 (3)4.748 (2)
C14···C223.318 (3)
C14···C233.297 (3)
C14···C243.491 (3)3.231 (3)
C14···C253.749 (3)
C14···C262.925 (3)
Torsion angles (°) of the chain segments top
(1)(2)
C4—O1—C17—C1893.8 (2)-72.9 (2)
O1—C17—C18—C19-73.3 (3)78.5 (2)
C17—C18—C19—C20-77.2 (3)67.6 (2)
C18—C19—C20—C21175.0 (2)169.0 (2)
C19—C20—C21—C22-80.9 (3)76.7 (2)
C20—C21—C22—C23-175.3 (2)-178.8 (2)
C21—C22—C23—C24175.0 (2)164.1 (2)
C22—C23—C24—C25163.3 (2)
C23—C24—C25—C26-73.3 (3)
C24—C25—C26—O2-66.1 (3)
C25—C26—O2—C1395.8 (2)
C22—C23—C24—O2-88.4 (3)
C23—C24—O2—C1366.0 (3)
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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