4,4′-Diethynylbiphenyl crystallizes with four unique molecules in the asymmetric unit. The crystal structure is stabilized by weak C—H⋯π(ring) and C C—H⋯π(alkyne) contacts.
Keywords: crystal structure; 4,4′-diethynylbiphenyl; C—H⋯π(ring) interactions; C C—H⋯π contacts
Abstract
The title compound, C16H10, crystallizes with four unique molecules, designated 1–4, in the asymmetric unit of the monoclinic unit cell. None of the molecules is planar, with the benzene rings of molecules 1–4 inclined to one another at angles of 42.41 (4), 24.07 (6), 42.59 (4) and 46.88 (4)°, respectively. In the crystal, weak C—H⋯π(ring) interactions, augmented by even weaker C C—H⋯π(alkyne) contacts, generate a three-dimensional network structure with interlinked columns of molecules formed along the c-axis direction.
Chemical context
Donor–acceptor (D–A) dyads with the innate ability to generate long-lived charge separation in their excited states have elicited a great deal of current interest. Their applications cover fields ranging from artificial photosynthesis to solar cell technology (Rogozina et al., 2013 ▸; Fukuzumi et al., 2014 ▸). We have produced a variety of such dyads based on ferrocene as the donor and with a variety of acceptors (see for example: Flood et al., 2007 ▸; Cuffe et al., 2005 ▸; McAdam et al., 2003 ▸). More recently, we have been interested in expanding the range of donor–acceptor dyads by interpolating a potentially conductive spacer between the donor and the acceptor to yield donor–spacer–acceptor (D–S–A) dyads. Biphenyl is a conductive spacer that we have used with some recent success, joined to a ferrocene donor through an alkene unit and to an acceptor via an alkyne link (McAdam et al., 2010 ▸; Tagg et al., 2015 ▸). We are interested in further developing the chemistry of biphenyl as a potential spacer, with alkyne links to both the donor and the acceptor. Surprisingly, the molecular and crystal structure of the precursor molecule, 4,4′-diethynylbiphenyl (Liu, Liu et al., 2005 ▸), has not been previously studied and we report its structure here.
Structural commentary
The title compound, (I), crystallizes with four unique molecules in the asymmetric unit, identified by the leading digits 1–4 in the numbering schemes, Fig. 1 ▸. Each molecule comprises a central biphenyl ring system symmetrically substituted at the 4 and 4′ positions by terminal alkyne units. None of the molecules is planar, with the two benzene rings of each molecule inclined to one another at angles of 42.41 (4), 24.07 (6), 42.59 (4) and 46.88 (4)° for molecules 1–4, respectively. Bond distances and angles in the biphenyl ring systems are not unusual and compare well, both internally, over the four unique molecules, and with those observed in related systems (see for example: O’Brien et al., 2010 ▸, Butler et al., 2008 ▸; Muller, et al., 2006 ▸, Nitsche et al., 2003 ▸). The Cn4—Cn7 and Cn4′—Cn7′ distances (n = 1–4) [mean 1.445 (2) Å] are generally somewhat long, enough indeed to raise alerts in the checkCIF procedure. However analysis in Vista (Groom & Allen, 2014 ▸) of comparable values for eight other biphenyl systems, with terminal alkyne functions in the 4-position, provides a mean value of 1.442 (16) Å, not at all dissimilar to the values observed here (see for example: Langley et al., 1998 ▸; Mague et al., 1997 ▸; McAdam et al., 2010 ▸; Laliberté et al., 2006 ▸). The C C distances are also generally reasonable, with the exception of C27′—C28′, 1.130 (2) Å, which is unusually short compared to more typical C C distances of 1.181 (14) Å (Allen et al. 1987 ▸). There is no obvious explanation for this, except to note that the adjacent C27′—C24′ distance 1.4507 (19) Å is the longest of those reported here.
Figure 1.
The asymmetric unit of (I), showing the numbering schemes for the four unique molecules designated as types 1–4 with the types discriminated by the leading characters in the atom labels.
Supramolecular features
The absence of donor and acceptor components, to provide classical hydrogen bonding or even C—H⋯E (E = O, N, halogen) contacts, challenge the packing in this system. There has been considerable speculation on the factors influencing the formation of structures with Z′ > 1 (Desiraju, 2007 ▸; Steed & Steed, 2015 ▸; Anderson & Steed 2007 ▸, Nichol & Clegg, 2007 ▸), and the nature, extent and degree of the intermolecular contacts are clearly contributory factors. In this instance, the packing in the structure is profoundly influenced by an extensive series of weak edge-to-face C—H⋯π(ring) interactions (Table 1 ▸) augmented by still weaker C C—H⋯π(alkyne) contacts. It is likely that the inherent weakness of these contacts may influence the adoption of a Z′ > 1 structure.
Table 1. CH interactions (, ).
Cg1, Cg3, Cg4, Cg6 and Cg8 are the centroids of the C11C16, C21C26, C21C26, C31C36 and C41C46 rings, respectively.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C13H13Cg6i | 0.95 | 2.73 | 3.4910(13) | 137 |
| C15H15Cg6 | 0.95 | 2.70 | 3.4782(13) | 140 |
| C16H16Cg1ii | 0.95 | 2.92 | 3.5375(12) | 124 |
| C23H23Cg8i | 0.95 | 2.71 | 3.4809(13) | 139 |
| C25H25Cg8 | 0.95 | 2.76 | 3.4976(14) | 136 |
| C33H33Cg4iii | 0.95 | 2.88 | 3.6153(13) | 135 |
| C36H36Cg3iii | 0.95 | 2.87 | 3.6112(12) | 135 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
.
A complementary set of C—H⋯π contacts, involving in one case molecules 1 and 3 and in the second molecules 2 and 4, sandwiches a molecule of 1 between two molecules of 3 and a molecule of 2 between two molecules of 4. These contacts generate infinite chains approximately along the c-axis direction. The two chains lie approximately orthogonal to one another, Fig. 2 ▸. Weak C16′—H16′⋯Cg1 contacts form inversion dimers between two adjacent 1 molecules, Fig. 3 ▸, and dimers also result from C—H⋯π contacts involving both rings of adjacent 2 and 3 molecules, Fig. 4 ▸; both these sets of contacts contribute to the overall packing. In addition to these C—H⋯π(ring) interactions, one further set of somewhat unusual contacts is formed, again involving all four molecules in the structure. These are weak C C—H⋯π(alkyne) contacts (Desiraju & Steiner, 1999 ▸) involving the relatively acidic C—H donors of the alkyne substituents. These again involve pairs of molecules with C18—H18⋯C37 C38 and C38′—H38′⋯C17′ C18′ contacts generating one set of zigzag chains along b with an adjacent and complementary zigzag produced by C28—H28⋯C47 C48 and C48′—H48′⋯C27′ C28′ interactions, These chains generate layers of molecules in the ac plane, Fig. 5 ▸. The contacts display the classic T shape, found also in the neutron structure of acetylene (McMullan et al., 1992 ▸), but not perfectly so. The Hn8⋯Cn7 distances are consistently slightly shorter [mean of the four distances = 2.77 (3) Å] than the Hn8⋯Cn8 equivalents [mean 2.97 (4) Å]. The mean Hn8⋯C C centroid distance is 2.82 (4) Å and these values all fall well within projected ranges for such contacts (Desiraju & Steiner, 1999 ▸). The overall effect of this plethora of weak interactions is to stack molecules into ‘multiple-decker sandwich’ columns, linked together along the c-axis direction, Fig. 6 ▸.
Figure 2.
Complementary chains of 1, 3 and 2, 4 molecules extending along the c-axis direction. In this and subsequent figures, C—H⋯π(ring) contacts are drawn as dotted lines with ring centroids shown as coloured spheres.
Figure 3.
Inversion dimers formed through C—H⋯π(ring) contacts between molecules of type 1.
Figure 4.
Dimers formed through C—H⋯π(ring) contacts between molecules of types 2 and 4.
Figure 5.
Zigzag chains of molecules generated by C—H⋯C C contacts between molecules of types 1 and 3 and molecules of types 2 and 4. The centroids of the C C bonds are drawn as coloured spheres and the C—H⋯C C contacts are shown as dotted lines.
Figure 6.
Overall packing for (I) viewed along the c axis. Representative C—H⋯π(ring) and C—H⋯π(alkyne) contacts are drawn as dotted lines.
Database survey
Structures of 4-4′-disubstituted biphenyls abound with 2891 hits on the CSD (Groom & Allen, 2014 ▸). However, those with 4,4′-alkyne substituents are far less plentiful with only 29 entries. These fall into two distinct categories. First compounds with one or both of the alkyne substituents on the biphenyls bound to carbon or silicon atoms, 14 entries (see for example: Zhou et al., 2012 ▸; McAdam et al., 2010 ▸; O’Brien et al., 2010 ▸, Zeng et al., 2007 ▸; Muller, et al., 2006 ▸; Nitsche et al., 2003 ▸). Second, the well represented class of organometallic acetylides, also referred to as ethynyl compounds. These have either the terminal hydrogen atoms of the alkyne groups both replaced by a transition metal complex moiety (see for example: Shanmugaraju et al., 2011 ▸; Gao et al., 2007 ▸; Ibn Ghazala et al., 2006 ▸; Liu, Poon et al., 2005 ▸) or, much less frequently, only a single terminal hydrogen atom is replaced to afford ethynyl complexes with terminal C C–H substituents (Zeng et al., 2013 ▸; Saha et al., 2005 ▸).
Synthesis and crystallization
The title compound (I) was prepared by a literature procedure (Liu, Liu et al., 2005 ▸) and recrystallized from dichloromethane/hexane (1:1) to give pale-yellow plates suitable for X-ray analysis.
Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. All hydrogen atoms were refined using a riding model with d(C—H) = 0.95 Å, U iso = 1.2U eq(C) for both the aromatic and terminal alkyne H atoms. Two low angle reflections with F o << F c, with intensities likely to have been attenuated by the beam-stop, were removed for the final refinement cycles.
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C16H10 |
| M r | 202.24 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 85 |
| a, b, c () | 23.4263(5), 21.1181(5), 9.2989(2) |
| () | 100.731(1) |
| V (3) | 4519.89(17) |
| Z | 16 |
| Radiation type | Mo K |
| (mm1) | 0.07 |
| Crystal size (mm) | 0.46 0.40 0.07 |
| Data collection | |
| Diffractometer | BrukerNonius APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2011 ▸) |
| T min, T max | 0.887, 0.980 |
| No. of measured, independent and observed [I > 2(I)] reflections | 77658, 8885, 7147 |
| R int | 0.030 |
| (sin /)max (1) | 0.617 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.036, 0.103, 1.03 |
| No. of reflections | 8885 |
| No. of parameters | 577 |
| No. of restraints | 42 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.29, 0.16 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011494/hg5446sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011494/hg5446Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015011494/hg5446Isup3.cml
CCDC reference: 1406589
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
We thank the New Zealand Ministry of Business, Innovation and Employment, Science Investment Fund (grant No. UOO-X1206) for support of this work and the University of Otago for the purchase of the diffractometer.
supplementary crystallographic information
Crystal data
| C16H10 | F(000) = 1696 |
| Mr = 202.24 | Dx = 1.189 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| a = 23.4263 (5) Å | Cell parameters from 8416 reflections |
| b = 21.1181 (5) Å | θ = 4.9–62.5° |
| c = 9.2989 (2) Å | µ = 0.07 mm−1 |
| β = 100.731 (1)° | T = 85 K |
| V = 4519.89 (17) Å3 | Plate, pale yellow |
| Z = 16 | 0.46 × 0.40 × 0.07 mm |
Data collection
| Bruker–Nonius APEXII CCD diffractometer | 8885 independent reflections |
| Radiation source: fine-focus sealed tube | 7147 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.030 |
| φ and ω scans | θmax = 26.0°, θmin = 1.3° |
| Absorption correction: multi-scan (SADABS; Bruker, 2011) | h = −28→28 |
| Tmin = 0.887, Tmax = 0.980 | k = −26→26 |
| 77658 measured reflections | l = −11→11 |
Refinement
| Refinement on F2 | 42 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0471P)2 + 1.454P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.03 | (Δ/σ)max = 0.001 |
| 8885 reflections | Δρmax = 0.29 e Å−3 |
| 577 parameters | Δρmin = −0.16 e Å−3 |
Special details
| 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. Two low angle reflections with Fo << Fc with intensities affected by the beam-stop were removed for the final refinement cycles. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| C18 | 0.26084 (6) | 0.61801 (6) | 0.27932 (15) | 0.0318 (3) | |
| H18 | 0.2298 | 0.6477 | 0.2663 | 0.038* | |
| C17 | 0.29917 (5) | 0.58137 (6) | 0.29541 (13) | 0.0240 (3) | |
| C16 | 0.40471 (6) | 0.45861 (6) | 0.46859 (13) | 0.0252 (3) | |
| H16 | 0.4152 | 0.4381 | 0.5606 | 0.030* | |
| C15 | 0.36119 (5) | 0.50352 (6) | 0.44947 (13) | 0.0253 (3) | |
| H15 | 0.3417 | 0.5130 | 0.5278 | 0.030* | |
| C14 | 0.34553 (5) | 0.53520 (5) | 0.31607 (13) | 0.0206 (2) | |
| C13 | 0.37510 (5) | 0.52063 (6) | 0.20294 (13) | 0.0226 (3) | |
| H13 | 0.3657 | 0.5423 | 0.1121 | 0.027* | |
| C12 | 0.41799 (5) | 0.47484 (6) | 0.22237 (12) | 0.0221 (2) | |
| H12 | 0.4372 | 0.4650 | 0.1438 | 0.027* | |
| C11 | 0.43363 (5) | 0.44272 (5) | 0.35501 (12) | 0.0196 (2) | |
| C11' | 0.47811 (5) | 0.39198 (5) | 0.37373 (12) | 0.0197 (2) | |
| C12' | 0.47908 (5) | 0.34774 (5) | 0.26198 (12) | 0.0214 (2) | |
| H12' | 0.4516 | 0.3511 | 0.1732 | 0.026* | |
| C13' | 0.51937 (5) | 0.29931 (6) | 0.27899 (13) | 0.0229 (3) | |
| H13' | 0.5192 | 0.2696 | 0.2023 | 0.027* | |
| C15' | 0.56013 (5) | 0.33806 (5) | 0.52006 (13) | 0.0231 (3) | |
| H15' | 0.5880 | 0.3351 | 0.6082 | 0.028* | |
| C16' | 0.51939 (5) | 0.38625 (5) | 0.50273 (12) | 0.0222 (2) | |
| H16' | 0.5195 | 0.4159 | 0.5796 | 0.027* | |
| C14' | 0.56056 (5) | 0.29371 (5) | 0.40853 (13) | 0.0212 (2) | |
| C17' | 0.60326 (5) | 0.24352 (6) | 0.42461 (13) | 0.0242 (3) | |
| C18' | 0.63815 (6) | 0.20297 (6) | 0.43483 (14) | 0.0294 (3) | |
| H18' | 0.6663 | 0.1702 | 0.4431 | 0.035* | |
| C28 | 0.01222 (6) | 0.61620 (7) | −0.10611 (15) | 0.0359 (3) | |
| H28 | −0.0189 | 0.6457 | −0.1243 | 0.043* | |
| C27 | 0.05092 (6) | 0.57953 (6) | −0.08355 (14) | 0.0277 (3) | |
| C24 | 0.09698 (5) | 0.53344 (6) | −0.05973 (13) | 0.0231 (3) | |
| C25 | 0.12721 (6) | 0.51937 (6) | 0.08080 (14) | 0.0292 (3) | |
| H25 | 0.1184 | 0.5417 | 0.1626 | 0.035* | |
| C26 | 0.16983 (6) | 0.47332 (6) | 0.10195 (13) | 0.0280 (3) | |
| H26 | 0.1901 | 0.4647 | 0.1983 | 0.034* | |
| C23 | 0.11208 (5) | 0.50095 (6) | −0.17817 (13) | 0.0227 (3) | |
| H23 | 0.0931 | 0.5109 | −0.2750 | 0.027* | |
| C22 | 0.15419 (5) | 0.45468 (5) | −0.15572 (13) | 0.0217 (2) | |
| H22 | 0.1634 | 0.4327 | −0.2377 | 0.026* | |
| C21 | 0.18383 (5) | 0.43917 (5) | −0.01531 (13) | 0.0212 (2) | |
| C21' | 0.22840 (5) | 0.38863 (5) | 0.00710 (13) | 0.0219 (2) | |
| C22' | 0.22770 (5) | 0.33988 (6) | −0.09553 (13) | 0.0247 (3) | |
| H22' | 0.1977 | 0.3390 | −0.1798 | 0.030* | |
| C23' | 0.26965 (5) | 0.29318 (6) | −0.07676 (14) | 0.0278 (3) | |
| H23' | 0.2686 | 0.2610 | −0.1486 | 0.033* | |
| C25' | 0.31418 (5) | 0.34058 (6) | 0.15210 (14) | 0.0269 (3) | |
| H25' | 0.3433 | 0.3405 | 0.2381 | 0.032* | |
| C26' | 0.27264 (5) | 0.38763 (6) | 0.13152 (13) | 0.0240 (3) | |
| H26' | 0.2740 | 0.4200 | 0.2030 | 0.029* | |
| C24' | 0.31377 (5) | 0.29291 (6) | 0.04756 (14) | 0.0270 (3) | |
| C27' | 0.35848 (6) | 0.24449 (7) | 0.06802 (16) | 0.0352 (3) | |
| C28' | 0.39403 (7) | 0.20760 (7) | 0.08536 (18) | 0.0447 (4) | |
| H28' | 0.4239 | 0.1766 | 0.0999 | 0.054* | |
| C38 | 0.11161 (6) | 0.79841 (6) | 0.69494 (16) | 0.0334 (3) | |
| H38 | 0.0828 | 0.8306 | 0.6771 | 0.040* | |
| C37 | 0.14702 (5) | 0.75884 (6) | 0.71693 (14) | 0.0274 (3) | |
| C34 | 0.19066 (5) | 0.70967 (5) | 0.74066 (13) | 0.0231 (3) | |
| C35 | 0.18803 (5) | 0.66086 (6) | 0.84074 (13) | 0.0240 (3) | |
| H35 | 0.1577 | 0.6605 | 0.8958 | 0.029* | |
| C36 | 0.22913 (5) | 0.61314 (5) | 0.86027 (13) | 0.0218 (2) | |
| H36 | 0.2265 | 0.5800 | 0.9277 | 0.026* | |
| C33 | 0.23589 (5) | 0.70960 (6) | 0.66094 (13) | 0.0250 (3) | |
| H33 | 0.2381 | 0.7423 | 0.5920 | 0.030* | |
| C32 | 0.27727 (5) | 0.66226 (6) | 0.68221 (13) | 0.0229 (3) | |
| H32 | 0.3080 | 0.6631 | 0.6285 | 0.027* | |
| C31 | 0.27464 (5) | 0.61318 (5) | 0.78158 (12) | 0.0199 (2) | |
| C31' | 0.31938 (5) | 0.56270 (5) | 0.80312 (12) | 0.0192 (2) | |
| C32' | 0.30445 (5) | 0.49923 (5) | 0.81532 (12) | 0.0209 (2) | |
| H32' | 0.2648 | 0.4881 | 0.8105 | 0.025* | |
| C33' | 0.34629 (5) | 0.45206 (6) | 0.83436 (12) | 0.0220 (2) | |
| H33' | 0.3352 | 0.4091 | 0.8416 | 0.026* | |
| C35' | 0.41999 (5) | 0.53127 (6) | 0.83133 (12) | 0.0225 (2) | |
| H35' | 0.4597 | 0.5424 | 0.8375 | 0.027* | |
| C36' | 0.37810 (5) | 0.57790 (6) | 0.81118 (12) | 0.0211 (2) | |
| H36' | 0.3892 | 0.6208 | 0.8027 | 0.025* | |
| C34' | 0.40476 (5) | 0.46768 (6) | 0.84285 (12) | 0.0206 (2) | |
| C37' | 0.44936 (5) | 0.41951 (6) | 0.86414 (12) | 0.0237 (3) | |
| C38' | 0.48707 (6) | 0.38135 (6) | 0.88180 (14) | 0.0302 (3) | |
| H38' | 0.5173 | 0.3507 | 0.8960 | 0.036* | |
| C48 | −0.13344 (6) | 0.79702 (7) | 0.30586 (17) | 0.0402 (3) | |
| H48 | −0.1621 | 0.8292 | 0.2858 | 0.048* | |
| C47 | −0.09783 (6) | 0.75706 (6) | 0.33069 (15) | 0.0324 (3) | |
| C44 | −0.05457 (5) | 0.70779 (6) | 0.35722 (14) | 0.0272 (3) | |
| C45 | −0.05343 (5) | 0.66035 (6) | 0.25252 (14) | 0.0264 (3) | |
| H45 | −0.0811 | 0.6610 | 0.1637 | 0.032* | |
| C46 | −0.01241 (5) | 0.61263 (6) | 0.27733 (13) | 0.0241 (3) | |
| H46 | −0.0127 | 0.5804 | 0.2060 | 0.029* | |
| C43 | −0.01289 (6) | 0.70624 (6) | 0.48626 (15) | 0.0297 (3) | |
| H43 | −0.0132 | 0.7379 | 0.5586 | 0.036* | |
| C42 | 0.02873 (5) | 0.65901 (6) | 0.50944 (14) | 0.0270 (3) | |
| H42 | 0.0572 | 0.6591 | 0.5968 | 0.032* | |
| C41 | 0.02949 (5) | 0.61109 (6) | 0.40583 (13) | 0.0229 (3) | |
| C41' | 0.07433 (5) | 0.56078 (6) | 0.42969 (12) | 0.0219 (2) | |
| C42' | 0.13294 (5) | 0.57601 (6) | 0.47849 (13) | 0.0232 (3) | |
| H42' | 0.1439 | 0.6189 | 0.4983 | 0.028* | |
| C43' | 0.17498 (5) | 0.52946 (6) | 0.49820 (13) | 0.0243 (3) | |
| H43' | 0.2146 | 0.5407 | 0.5293 | 0.029* | |
| C45' | 0.10123 (5) | 0.45009 (6) | 0.42502 (13) | 0.0246 (3) | |
| H45' | 0.0902 | 0.4071 | 0.4081 | 0.030* | |
| C46' | 0.05956 (5) | 0.49710 (6) | 0.40248 (13) | 0.0238 (3) | |
| H46' | 0.0201 | 0.4860 | 0.3678 | 0.029* | |
| C44' | 0.15977 (5) | 0.46576 (6) | 0.47284 (12) | 0.0235 (3) | |
| C47' | 0.20428 (5) | 0.41762 (6) | 0.49536 (13) | 0.0273 (3) | |
| C48' | 0.24191 (6) | 0.37986 (7) | 0.51539 (15) | 0.0350 (3) | |
| H48' | 0.2723 | 0.3494 | 0.5316 | 0.042* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C18 | 0.0334 (7) | 0.0309 (7) | 0.0326 (7) | 0.0041 (6) | 0.0103 (6) | 0.0050 (6) |
| C17 | 0.0262 (6) | 0.0268 (6) | 0.0198 (6) | −0.0057 (5) | 0.0062 (5) | −0.0005 (5) |
| C16 | 0.0370 (7) | 0.0220 (6) | 0.0173 (6) | 0.0024 (5) | 0.0065 (5) | 0.0022 (5) |
| C15 | 0.0341 (7) | 0.0238 (6) | 0.0201 (6) | 0.0014 (5) | 0.0105 (5) | −0.0016 (5) |
| C14 | 0.0213 (6) | 0.0183 (5) | 0.0217 (6) | −0.0030 (4) | 0.0029 (5) | −0.0019 (4) |
| C13 | 0.0224 (6) | 0.0276 (6) | 0.0167 (6) | −0.0015 (5) | 0.0011 (4) | 0.0023 (5) |
| C12 | 0.0215 (6) | 0.0288 (6) | 0.0165 (6) | −0.0005 (5) | 0.0049 (4) | −0.0005 (5) |
| C11 | 0.0216 (6) | 0.0191 (6) | 0.0175 (6) | −0.0044 (5) | 0.0027 (4) | −0.0024 (4) |
| C11' | 0.0213 (6) | 0.0200 (6) | 0.0186 (6) | −0.0041 (5) | 0.0056 (4) | 0.0019 (4) |
| C12' | 0.0213 (6) | 0.0251 (6) | 0.0173 (6) | −0.0016 (5) | 0.0023 (4) | −0.0001 (5) |
| C13' | 0.0251 (6) | 0.0231 (6) | 0.0212 (6) | −0.0023 (5) | 0.0062 (5) | −0.0031 (5) |
| C15' | 0.0248 (6) | 0.0234 (6) | 0.0196 (6) | −0.0051 (5) | 0.0001 (5) | 0.0040 (5) |
| C16' | 0.0282 (6) | 0.0212 (6) | 0.0171 (6) | −0.0036 (5) | 0.0035 (5) | −0.0008 (4) |
| C14' | 0.0205 (6) | 0.0199 (6) | 0.0238 (6) | −0.0033 (5) | 0.0055 (5) | 0.0040 (5) |
| C17' | 0.0251 (6) | 0.0244 (6) | 0.0235 (6) | −0.0072 (5) | 0.0057 (5) | 0.0016 (5) |
| C18' | 0.0274 (7) | 0.0271 (7) | 0.0332 (7) | −0.0001 (6) | 0.0040 (5) | 0.0067 (5) |
| C28 | 0.0371 (8) | 0.0381 (8) | 0.0313 (7) | 0.0090 (6) | 0.0027 (6) | −0.0049 (6) |
| C27 | 0.0301 (7) | 0.0304 (7) | 0.0230 (6) | −0.0038 (6) | 0.0059 (5) | −0.0044 (5) |
| C24 | 0.0226 (6) | 0.0218 (6) | 0.0255 (6) | −0.0029 (5) | 0.0060 (5) | −0.0006 (5) |
| C25 | 0.0363 (7) | 0.0318 (7) | 0.0215 (6) | 0.0038 (6) | 0.0102 (5) | −0.0031 (5) |
| C26 | 0.0340 (7) | 0.0316 (7) | 0.0186 (6) | 0.0034 (6) | 0.0052 (5) | 0.0021 (5) |
| C23 | 0.0207 (6) | 0.0264 (6) | 0.0208 (6) | −0.0054 (5) | 0.0033 (5) | −0.0003 (5) |
| C22 | 0.0215 (6) | 0.0242 (6) | 0.0201 (6) | −0.0050 (5) | 0.0056 (5) | −0.0034 (5) |
| C21 | 0.0216 (6) | 0.0214 (6) | 0.0219 (6) | −0.0058 (5) | 0.0071 (5) | 0.0005 (5) |
| C21' | 0.0228 (6) | 0.0224 (6) | 0.0219 (6) | −0.0054 (5) | 0.0074 (5) | 0.0018 (5) |
| C22' | 0.0246 (6) | 0.0253 (6) | 0.0236 (6) | −0.0029 (5) | 0.0026 (5) | −0.0011 (5) |
| C23' | 0.0295 (7) | 0.0240 (6) | 0.0294 (7) | −0.0028 (5) | 0.0040 (5) | −0.0046 (5) |
| C25' | 0.0259 (6) | 0.0271 (6) | 0.0262 (6) | −0.0045 (5) | 0.0006 (5) | 0.0016 (5) |
| C26' | 0.0271 (6) | 0.0230 (6) | 0.0223 (6) | −0.0048 (5) | 0.0055 (5) | −0.0021 (5) |
| C24' | 0.0252 (6) | 0.0215 (6) | 0.0336 (7) | −0.0021 (5) | 0.0039 (5) | 0.0005 (5) |
| C27' | 0.0338 (7) | 0.0306 (7) | 0.0380 (8) | −0.0095 (6) | −0.0016 (6) | −0.0062 (6) |
| C28' | 0.0388 (8) | 0.0274 (7) | 0.0606 (10) | 0.0002 (7) | −0.0095 (7) | −0.0131 (7) |
| C38 | 0.0267 (7) | 0.0301 (7) | 0.0433 (8) | 0.0003 (6) | 0.0065 (6) | −0.0079 (6) |
| C37 | 0.0266 (6) | 0.0254 (6) | 0.0298 (7) | −0.0073 (5) | 0.0043 (5) | −0.0049 (5) |
| C34 | 0.0206 (6) | 0.0208 (6) | 0.0265 (6) | −0.0021 (5) | 0.0011 (5) | −0.0059 (5) |
| C35 | 0.0208 (6) | 0.0262 (6) | 0.0259 (6) | −0.0041 (5) | 0.0069 (5) | −0.0061 (5) |
| C36 | 0.0231 (6) | 0.0218 (6) | 0.0208 (6) | −0.0048 (5) | 0.0043 (5) | −0.0016 (5) |
| C33 | 0.0264 (6) | 0.0231 (6) | 0.0254 (6) | −0.0023 (5) | 0.0044 (5) | 0.0013 (5) |
| C32 | 0.0215 (6) | 0.0249 (6) | 0.0232 (6) | −0.0027 (5) | 0.0068 (5) | −0.0006 (5) |
| C31 | 0.0193 (5) | 0.0210 (6) | 0.0188 (6) | −0.0041 (5) | 0.0018 (4) | −0.0043 (4) |
| C31' | 0.0202 (6) | 0.0246 (6) | 0.0130 (5) | −0.0022 (5) | 0.0035 (4) | −0.0009 (4) |
| C32' | 0.0190 (5) | 0.0259 (6) | 0.0181 (6) | −0.0037 (5) | 0.0042 (4) | −0.0005 (5) |
| C33' | 0.0258 (6) | 0.0224 (6) | 0.0178 (6) | −0.0028 (5) | 0.0039 (5) | 0.0003 (5) |
| C35' | 0.0193 (6) | 0.0300 (6) | 0.0183 (6) | −0.0026 (5) | 0.0039 (4) | −0.0004 (5) |
| C36' | 0.0221 (6) | 0.0220 (6) | 0.0196 (6) | −0.0045 (5) | 0.0046 (5) | −0.0004 (5) |
| C34' | 0.0229 (6) | 0.0267 (6) | 0.0123 (5) | 0.0017 (5) | 0.0031 (4) | −0.0004 (4) |
| C37' | 0.0253 (6) | 0.0303 (7) | 0.0154 (6) | −0.0024 (5) | 0.0037 (5) | −0.0008 (5) |
| C38' | 0.0328 (7) | 0.0335 (7) | 0.0236 (6) | 0.0073 (6) | 0.0041 (5) | 0.0007 (5) |
| C48 | 0.0328 (8) | 0.0351 (8) | 0.0517 (9) | 0.0024 (6) | 0.0056 (7) | −0.0063 (7) |
| C47 | 0.0305 (7) | 0.0281 (7) | 0.0381 (8) | −0.0055 (6) | 0.0048 (6) | −0.0034 (6) |
| C44 | 0.0239 (6) | 0.0240 (6) | 0.0346 (7) | −0.0037 (5) | 0.0075 (5) | 0.0007 (5) |
| C45 | 0.0227 (6) | 0.0272 (6) | 0.0288 (7) | −0.0063 (5) | 0.0034 (5) | 0.0004 (5) |
| C46 | 0.0237 (6) | 0.0239 (6) | 0.0256 (6) | −0.0071 (5) | 0.0071 (5) | −0.0033 (5) |
| C43 | 0.0320 (7) | 0.0257 (7) | 0.0319 (7) | −0.0025 (5) | 0.0076 (6) | −0.0062 (5) |
| C42 | 0.0289 (6) | 0.0278 (6) | 0.0233 (6) | −0.0037 (5) | 0.0028 (5) | −0.0025 (5) |
| C41 | 0.0222 (6) | 0.0226 (6) | 0.0252 (6) | −0.0062 (5) | 0.0079 (5) | 0.0001 (5) |
| C41' | 0.0247 (6) | 0.0260 (6) | 0.0160 (5) | −0.0046 (5) | 0.0061 (5) | −0.0013 (5) |
| C42' | 0.0265 (6) | 0.0242 (6) | 0.0191 (6) | −0.0052 (5) | 0.0042 (5) | −0.0019 (5) |
| C43' | 0.0231 (6) | 0.0323 (7) | 0.0173 (6) | −0.0058 (5) | 0.0030 (5) | −0.0017 (5) |
| C45' | 0.0285 (6) | 0.0242 (6) | 0.0224 (6) | −0.0048 (5) | 0.0080 (5) | −0.0025 (5) |
| C46' | 0.0220 (6) | 0.0271 (6) | 0.0229 (6) | −0.0045 (5) | 0.0061 (5) | −0.0024 (5) |
| C44' | 0.0269 (6) | 0.0291 (6) | 0.0153 (6) | 0.0006 (5) | 0.0060 (5) | −0.0006 (5) |
| C47' | 0.0293 (7) | 0.0333 (7) | 0.0192 (6) | −0.0042 (6) | 0.0046 (5) | −0.0034 (5) |
| C48' | 0.0377 (8) | 0.0360 (8) | 0.0300 (7) | 0.0065 (6) | 0.0032 (6) | −0.0031 (6) |
Geometric parameters (Å, º)
| C18—C17 | 1.1736 (18) | C38—C37 | 1.1684 (18) |
| C18—H18 | 0.9500 | C38—H38 | 0.9500 |
| C17—C14 | 1.4454 (17) | C37—C34 | 1.4450 (17) |
| C16—C15 | 1.3795 (17) | C34—C35 | 1.3977 (17) |
| C16—C11 | 1.3977 (16) | C34—C33 | 1.4018 (17) |
| C16—H16 | 0.9500 | C35—C36 | 1.3823 (17) |
| C15—C14 | 1.3968 (17) | C35—H35 | 0.9500 |
| C15—H15 | 0.9500 | C36—C31 | 1.4009 (16) |
| C14—C13 | 1.3974 (16) | C36—H36 | 0.9500 |
| C13—C12 | 1.3820 (17) | C33—C32 | 1.3809 (17) |
| C13—H13 | 0.9500 | C33—H33 | 0.9500 |
| C12—C11 | 1.3955 (16) | C32—C31 | 1.3976 (16) |
| C12—H12 | 0.9500 | C32—H32 | 0.9500 |
| C11—C11' | 1.4821 (16) | C31—C31' | 1.4820 (16) |
| C11'—C16' | 1.3988 (16) | C31'—C32' | 1.3953 (16) |
| C11'—C12' | 1.4008 (16) | C31'—C36' | 1.4009 (15) |
| C12'—C13' | 1.3806 (16) | C32'—C33' | 1.3854 (16) |
| C12'—H12' | 0.9500 | C32'—H32' | 0.9500 |
| C13'—C14' | 1.4011 (17) | C33'—C34' | 1.3968 (16) |
| C13'—H13' | 0.9500 | C33'—H33' | 0.9500 |
| C15'—C16' | 1.3839 (17) | C35'—C36' | 1.3783 (16) |
| C15'—C14' | 1.3989 (17) | C35'—C34' | 1.3986 (16) |
| C15'—H15' | 0.9500 | C35'—H35' | 0.9500 |
| C16'—H16' | 0.9500 | C36'—H36' | 0.9500 |
| C14'—C17' | 1.4459 (17) | C34'—C37' | 1.4452 (17) |
| C17'—C18' | 1.1753 (18) | C37'—C38' | 1.1843 (18) |
| C18'—H18' | 0.9500 | C38'—H38' | 0.9500 |
| C28—C27 | 1.1810 (19) | C48—C47 | 1.179 (2) |
| C28—H28 | 0.9500 | C48—H48 | 0.9500 |
| C27—C24 | 1.4394 (17) | C47—C44 | 1.4413 (18) |
| C24—C25 | 1.3974 (17) | C44—C43 | 1.3993 (18) |
| C24—C23 | 1.3979 (17) | C44—C45 | 1.4008 (18) |
| C25—C26 | 1.3815 (18) | C45—C46 | 1.3820 (17) |
| C25—H25 | 0.9500 | C45—H45 | 0.9500 |
| C26—C21 | 1.3963 (17) | C46—C41 | 1.3984 (17) |
| C26—H26 | 0.9500 | C46—H46 | 0.9500 |
| C23—C22 | 1.3765 (17) | C43—C42 | 1.3834 (18) |
| C23—H23 | 0.9500 | C43—H43 | 0.9500 |
| C22—C21 | 1.3988 (16) | C42—C41 | 1.3997 (17) |
| C22—H22 | 0.9500 | C42—H42 | 0.9500 |
| C21—C21' | 1.4803 (17) | C41—C41' | 1.4814 (17) |
| C21'—C22' | 1.4019 (17) | C41'—C46' | 1.3998 (17) |
| C21'—C26' | 1.4023 (17) | C41'—C42' | 1.4009 (16) |
| C22'—C23' | 1.3803 (17) | C42'—C43' | 1.3793 (17) |
| C22'—H22' | 0.9500 | C42'—H42' | 0.9500 |
| C23'—C24' | 1.3999 (18) | C43'—C44' | 1.4003 (17) |
| C23'—H23' | 0.9500 | C43'—H43' | 0.9500 |
| C25'—C26' | 1.3790 (17) | C45'—C46' | 1.3806 (17) |
| C25'—C24' | 1.3982 (18) | C45'—C44' | 1.4004 (17) |
| C25'—H25' | 0.9500 | C45'—H45' | 0.9500 |
| C26'—H26' | 0.9500 | C46'—H46' | 0.9500 |
| C24'—C27' | 1.4507 (19) | C44'—C47' | 1.4433 (18) |
| C27'—C28' | 1.130 (2) | C47'—C48' | 1.1776 (19) |
| C28'—H28' | 0.9500 | C48'—H48' | 0.9500 |
| C17—C18—H18 | 180.0 | C37—C38—H38 | 180.0 |
| C18—C17—C14 | 178.75 (13) | C38—C37—C34 | 178.73 (14) |
| C15—C16—C11 | 121.21 (11) | C35—C34—C33 | 118.87 (11) |
| C15—C16—H16 | 119.4 | C35—C34—C37 | 120.93 (11) |
| C11—C16—H16 | 119.4 | C33—C34—C37 | 120.19 (11) |
| C16—C15—C14 | 120.62 (11) | C36—C35—C34 | 120.60 (11) |
| C16—C15—H15 | 119.7 | C36—C35—H35 | 119.7 |
| C14—C15—H15 | 119.7 | C34—C35—H35 | 119.7 |
| C15—C14—C13 | 118.56 (11) | C35—C36—C31 | 120.68 (11) |
| C15—C14—C17 | 120.51 (11) | C35—C36—H36 | 119.7 |
| C13—C14—C17 | 120.93 (10) | C31—C36—H36 | 119.7 |
| C12—C13—C14 | 120.40 (11) | C32—C33—C34 | 120.30 (11) |
| C12—C13—H13 | 119.8 | C32—C33—H33 | 119.8 |
| C14—C13—H13 | 119.8 | C34—C33—H33 | 119.8 |
| C13—C12—C11 | 121.36 (11) | C33—C32—C31 | 121.03 (11) |
| C13—C12—H12 | 119.3 | C33—C32—H32 | 119.5 |
| C11—C12—H12 | 119.3 | C31—C32—H32 | 119.5 |
| C12—C11—C16 | 117.83 (11) | C32—C31—C36 | 118.51 (11) |
| C12—C11—C11' | 121.22 (10) | C32—C31—C31' | 120.38 (10) |
| C16—C11—C11' | 120.92 (10) | C36—C31—C31' | 121.11 (10) |
| C16'—C11'—C12' | 118.31 (11) | C32'—C31'—C36' | 118.30 (11) |
| C16'—C11'—C11 | 121.46 (10) | C32'—C31'—C31 | 121.36 (10) |
| C12'—C11'—C11 | 120.22 (10) | C36'—C31'—C31 | 120.34 (10) |
| C13'—C12'—C11' | 120.95 (11) | C33'—C32'—C31' | 121.27 (11) |
| C13'—C12'—H12' | 119.5 | C33'—C32'—H32' | 119.4 |
| C11'—C12'—H12' | 119.5 | C31'—C32'—H32' | 119.4 |
| C12'—C13'—C14' | 120.52 (11) | C32'—C33'—C34' | 120.02 (11) |
| C12'—C13'—H13' | 119.7 | C32'—C33'—H33' | 120.0 |
| C14'—C13'—H13' | 119.7 | C34'—C33'—H33' | 120.0 |
| C16'—C15'—C14' | 120.40 (11) | C36'—C35'—C34' | 120.73 (11) |
| C16'—C15'—H15' | 119.8 | C36'—C35'—H35' | 119.6 |
| C14'—C15'—H15' | 119.8 | C34'—C35'—H35' | 119.6 |
| C15'—C16'—C11' | 121.01 (11) | C35'—C36'—C31' | 120.72 (11) |
| C15'—C16'—H16' | 119.5 | C35'—C36'—H36' | 119.6 |
| C11'—C16'—H16' | 119.5 | C31'—C36'—H36' | 119.6 |
| C15'—C14'—C13' | 118.81 (11) | C33'—C34'—C35' | 118.94 (11) |
| C15'—C14'—C17' | 120.96 (11) | C33'—C34'—C37' | 121.18 (11) |
| C13'—C14'—C17' | 120.22 (11) | C35'—C34'—C37' | 119.87 (10) |
| C18'—C17'—C14' | 178.63 (13) | C38'—C37'—C34' | 178.12 (13) |
| C17'—C18'—H18' | 180.0 | C37'—C38'—H38' | 180.0 |
| C27—C28—H28 | 180.0 | C47—C48—H48 | 180.0 |
| C28—C27—C24 | 178.05 (14) | C48—C47—C44 | 178.56 (15) |
| C25—C24—C23 | 118.29 (11) | C43—C44—C45 | 118.61 (11) |
| C25—C24—C27 | 121.50 (11) | C43—C44—C47 | 121.32 (12) |
| C23—C24—C27 | 120.21 (11) | C45—C44—C47 | 120.08 (12) |
| C26—C25—C24 | 120.65 (11) | C46—C45—C44 | 120.54 (12) |
| C26—C25—H25 | 119.7 | C46—C45—H45 | 119.7 |
| C24—C25—H25 | 119.7 | C44—C45—H45 | 119.7 |
| C25—C26—C21 | 121.40 (11) | C45—C46—C41 | 121.01 (11) |
| C25—C26—H26 | 119.3 | C45—C46—H46 | 119.5 |
| C21—C26—H26 | 119.3 | C41—C46—H46 | 119.5 |
| C22—C23—C24 | 120.55 (11) | C42—C43—C44 | 120.63 (12) |
| C22—C23—H23 | 119.7 | C42—C43—H43 | 119.7 |
| C24—C23—H23 | 119.7 | C44—C43—H43 | 119.7 |
| C23—C22—C21 | 121.67 (11) | C43—C42—C41 | 120.86 (12) |
| C23—C22—H22 | 119.2 | C43—C42—H42 | 119.6 |
| C21—C22—H22 | 119.2 | C41—C42—H42 | 119.6 |
| C26—C21—C22 | 117.39 (11) | C46—C41—C42 | 118.33 (11) |
| C26—C21—C21' | 121.63 (11) | C46—C41—C41' | 120.66 (11) |
| C22—C21—C21' | 120.98 (11) | C42—C41—C41' | 120.99 (11) |
| C22'—C21'—C26' | 117.62 (11) | C46'—C41'—C42' | 118.25 (11) |
| C22'—C21'—C21 | 121.01 (11) | C46'—C41'—C41 | 121.16 (10) |
| C26'—C21'—C21 | 121.37 (11) | C42'—C41'—C41 | 120.58 (11) |
| C23'—C22'—C21' | 121.39 (11) | C43'—C42'—C41' | 120.79 (11) |
| C23'—C22'—H22' | 119.3 | C43'—C42'—H42' | 119.6 |
| C21'—C22'—H22' | 119.3 | C41'—C42'—H42' | 119.6 |
| C22'—C23'—C24' | 120.41 (12) | C42'—C43'—C44' | 120.62 (11) |
| C22'—C23'—H23' | 119.8 | C42'—C43'—H43' | 119.7 |
| C24'—C23'—H23' | 119.8 | C44'—C43'—H43' | 119.7 |
| C26'—C25'—C24' | 120.59 (11) | C46'—C45'—C44' | 120.07 (11) |
| C26'—C25'—H25' | 119.7 | C46'—C45'—H45' | 120.0 |
| C24'—C25'—H25' | 119.7 | C44'—C45'—H45' | 120.0 |
| C25'—C26'—C21' | 121.30 (11) | C45'—C46'—C41' | 121.30 (11) |
| C25'—C26'—H26' | 119.4 | C45'—C46'—H46' | 119.3 |
| C21'—C26'—H26' | 119.4 | C41'—C46'—H46' | 119.3 |
| C25'—C24'—C23' | 118.66 (11) | C43'—C44'—C45' | 118.94 (11) |
| C25'—C24'—C27' | 120.33 (12) | C43'—C44'—C47' | 119.87 (11) |
| C23'—C24'—C27' | 121.01 (12) | C45'—C44'—C47' | 121.19 (11) |
| C28'—C27'—C24' | 178.68 (15) | C48'—C47'—C44' | 177.80 (14) |
| C27'—C28'—H28' | 180.0 | C47'—C48'—H48' | 180.0 |
Hydrogen-bond geometry (Å, º)
Cg1, Cg3, Cg4, Cg6 and Cg8 are the centroids of the C11–C16, C21–C26, C21'–C26', C31'–C36' and C41'–C46' rings, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C13—H13···Cg6i | 0.95 | 2.73 | 3.4910 (13) | 137 |
| C15—H15···Cg6 | 0.95 | 2.70 | 3.4782 (13) | 140 |
| C16′—H16′···Cg1ii | 0.95 | 2.92 | 3.5375 (12) | 124 |
| C23—H23···Cg8i | 0.95 | 2.71 | 3.4809 (13) | 139 |
| C25—H25···Cg8 | 0.95 | 2.76 | 3.4976 (14) | 136 |
| C33′—H33′···Cg4iii | 0.95 | 2.88 | 3.6153 (13) | 135 |
| C36—H36···Cg3iii | 0.95 | 2.87 | 3.6112 (12) | 135 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) x, y, z+1.
References
- Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338.
- Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015011494/hg5446sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015011494/hg5446Isup2.hkl
Supporting information file. DOI: 10.1107/S2056989015011494/hg5446Isup3.cml
CCDC reference: 1406589
Additional supporting information: crystallographic information; 3D view; checkCIF report