Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040639/hg2276sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040639/hg2276Isup2.hkl |
CCDC reference: 660327
(R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl was prepared according to the method reported in the literature (Kobayashi, 1998). A solid of (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl (0.2 mmol) was added to the benzene solution (8 ml). The unsolved compounds was filtered and slowly evaporated to generate white single crystals suitable for X-ray diffraction analysis. Elemental analysis [found (calculated)] for C36H18N4O2: C 80.29 (80.40), H 3.37 (3.58), N 10.40% (10.62%). In the IR spectrum the cyano vibration is observed at 2238 cm-1.
The benzene solvate (C37–C42) was restrained to be planar regular hexagons, with target C≐C distances of 1.39 (1) Å. H atoms were placed in calculated positions and were included in the refinement in the riding-model approximation, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The configuration of (I) was selected on the basis of the known configuration of the starting reagent, (R)-1,1'-binaphthalene-2,2'-diol, and Friedel pairs were merged.
(R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl as well as its derivative chiral non-entrosymmetrically phthalocyanines play an important role in the molecular self-assembly and molecular recognition in chemical, physical and biological sciences, since can form metal complexes with rare earth, actinide, and some early transition metals and main-group elements. (Kobayashi et al., 1999: Buchler & Ng, 2000).
To date, a variety of chiral supramolecular architectures have been obtained based on the above mentioned multifunctional ligands (Jiang & Lin, 2006). More recently, two novel interlocked chiral nanotubes formed from Ni(acac)2 and C2-symmetric 1,1-binaphthyl-6,6'-bipyridines have been reported (Jiang & Lin, 2003). They pointed out that the twisted binding sites of chiral rigid ditopic bridging ligands based on the 1,1'-binaphthyl unit will induce the formation of helical structures when linked by a linear metal-connecting point. Herein, we report the synthesis and crystal structure of a chiral organic compound (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl benzene solvate (I).
The molecular structure of (I) is shown in Fig. 1. The cyano group C—N bond distances in this compound range from 1.138 (5) to 1.153 (6) Å and are similar to those in inorganic coordinated complexes (Ni, Kou, Zhang et al., 2005; Ni, Kou, Zhao et al., 2005). The C18—C19 bond distance is 1.495 (4) Å. The ten carbon atoms from two naphthyl rings in the title compound, respectively, are almost coplanar with the largest deviation value of 0.0527 (5) Å and 0.0138 (5) Å from the mean plane. The dihedral angle between the two naphthyl rings is 79.5 (5)°, which are similar to that of its derivative (R)-3,3'-Dibromo-2,2'-dimethoxy-5,5',6,6',7,7',8,8'-octahydro-1,1'- binaphthalene (80.2 (3)°) (He & Ng, 2006) and significantly larger than that of (R)-3,3'-Bis(3,4,5-trifluorophenyl)-1,1'-binaphthalene-2,2'-diol (73.5 (1)°) (Kang et al., 2007) due to steric effects.
In (I), the (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl units are connected together by the intermolecular π–π interactions leading to chiral helical one-dimensional supramolecular structures as shown in Fig. 2.
For related literature, see: Buchler & Ng (2000); He & Ng (2006); Jiang & Lin (2003, 2006); Kang et al. (2007); Kobayashi (1998); Kobayashi et al. (1999); Ni, Kou, Zhang et al. (2005); Ni, Kou, Zhao et al. (2005).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: SHELXTL (Bruker, 2001).
C36H18N4O2·C6H6 | F(000) = 1280 |
Mr = 616.65 | Dx = 1.196 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3821 reflections |
a = 7.8783 (1) Å | θ = 2.3–26.0° |
b = 12.2854 (2) Å | µ = 0.08 mm−1 |
c = 35.3968 (5) Å | T = 295 K |
V = 3425.99 (9) Å3 | Block, colourless |
Z = 4 | 0.28 × 0.16 × 0.12 mm |
Bruker APEXII CCD area-detector diffractometer | 3821 independent reflections |
Radiation source: fine-focus sealed tube | 2647 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −9→9 |
Tmin = 0.979, Tmax = 0.991 | k = −10→15 |
18358 measured reflections | l = −43→43 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.147P)2 + 0.3168P] where P = (Fo2 + 2Fc2)/3 |
3821 reflections | (Δ/σ)max < 0.001 |
433 parameters | Δρmax = 0.28 e Å−3 |
15 restraints | Δρmin = −0.15 e Å−3 |
C36H18N4O2·C6H6 | V = 3425.99 (9) Å3 |
Mr = 616.65 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.8783 (1) Å | µ = 0.08 mm−1 |
b = 12.2854 (2) Å | T = 295 K |
c = 35.3968 (5) Å | 0.28 × 0.16 × 0.12 mm |
Bruker APEXII CCD area-detector diffractometer | 3821 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 2647 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.991 | Rint = 0.029 |
18358 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 15 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.28 e Å−3 |
3821 reflections | Δρmin = −0.15 e Å−3 |
433 parameters |
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 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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1382 (3) | 0.24330 (18) | 0.85664 (7) | 0.0668 (7) | |
O2 | 0.3103 (4) | −0.0648 (2) | 0.86696 (7) | 0.0737 (7) | |
N2 | 0.5117 (6) | 0.3449 (3) | 0.89188 (12) | 0.1093 (14) | |
N1 | 0.4688 (7) | 0.6613 (4) | 0.87275 (19) | 0.153 (2) | |
N3 | 0.4446 (6) | −0.0563 (4) | 0.70672 (12) | 0.1135 (14) | |
N4 | 0.2478 (5) | −0.2275 (3) | 0.78731 (10) | 0.0940 (12) | |
C1 | 0.3576 (7) | 0.6042 (4) | 0.86531 (16) | 0.0984 (15) | |
C2 | 0.2210 (5) | 0.5334 (3) | 0.85618 (11) | 0.0674 (10) | |
C3 | 0.0708 (5) | 0.5749 (3) | 0.84235 (12) | 0.0767 (11) | |
H3 | 0.0586 | 0.6495 | 0.8386 | 0.092* | |
C4 | −0.0598 (5) | 0.5060 (3) | 0.83415 (11) | 0.0744 (11) | |
H4 | −0.1625 | 0.5345 | 0.8258 | 0.089* | |
C5 | −0.0423 (5) | 0.3943 (3) | 0.83802 (10) | 0.0658 (9) | |
H5 | −0.1318 | 0.3482 | 0.8319 | 0.079* | |
C6 | 0.1085 (5) | 0.3523 (3) | 0.85096 (9) | 0.0576 (9) | |
C7 | 0.2408 (5) | 0.4210 (3) | 0.86122 (9) | 0.0588 (9) | |
C8 | 0.3917 (6) | 0.3773 (3) | 0.87786 (11) | 0.0729 (11) | |
C9 | 0.0561 (4) | 0.1644 (3) | 0.83539 (9) | 0.0533 (8) | |
C10 | 0.0262 (5) | 0.1796 (3) | 0.79661 (9) | 0.0630 (9) | |
H10 | 0.0523 | 0.2456 | 0.7852 | 0.076* | |
C11 | −0.0408 (5) | 0.0972 (3) | 0.77607 (9) | 0.0650 (10) | |
H11 | −0.0565 | 0.1065 | 0.7502 | 0.078* | |
C12 | −0.0872 (4) | −0.0024 (3) | 0.79300 (9) | 0.0572 (9) | |
C13 | −0.1665 (5) | −0.0864 (4) | 0.77246 (11) | 0.0735 (11) | |
H13 | −0.1823 | −0.0788 | 0.7466 | 0.088* | |
C14 | −0.2198 (5) | −0.1778 (4) | 0.78994 (15) | 0.0869 (13) | |
H14 | −0.2738 | −0.2320 | 0.7761 | 0.104* | |
C15 | −0.1943 (5) | −0.1916 (3) | 0.82898 (14) | 0.0794 (11) | |
H15 | −0.2339 | −0.2542 | 0.8408 | 0.095* | |
C16 | −0.1127 (5) | −0.1147 (3) | 0.84941 (11) | 0.0653 (9) | |
H16 | −0.0935 | −0.1261 | 0.8750 | 0.078* | |
C17 | −0.0560 (4) | −0.0170 (3) | 0.83221 (9) | 0.0527 (8) | |
C18 | 0.0245 (4) | 0.0673 (2) | 0.85308 (8) | 0.0490 (7) | |
C19 | 0.0871 (5) | 0.0476 (3) | 0.89238 (8) | 0.0548 (8) | |
C20 | 0.0049 (5) | 0.0909 (3) | 0.92492 (8) | 0.0609 (9) | |
C21 | −0.1454 (6) | 0.1520 (3) | 0.92207 (10) | 0.0766 (11) | |
H21 | −0.1930 | 0.1652 | 0.8985 | 0.092* | |
C22 | −0.2222 (7) | 0.1922 (4) | 0.95379 (12) | 0.1017 (15) | |
H22 | −0.3217 | 0.2324 | 0.9516 | 0.122* | |
C23 | −0.1520 (9) | 0.1732 (5) | 0.98937 (13) | 0.1127 (18) | |
H23 | −0.2053 | 0.2007 | 1.0108 | 0.135* | |
C24 | −0.0090 (8) | 0.1158 (4) | 0.99294 (11) | 0.0977 (15) | |
H24 | 0.0367 | 0.1046 | 1.0169 | 0.117* | |
C25 | 0.0740 (6) | 0.0717 (3) | 0.96123 (9) | 0.0737 (11) | |
C26 | 0.2243 (8) | 0.0088 (4) | 0.96445 (11) | 0.0979 (15) | |
H26 | 0.2711 | −0.0036 | 0.9882 | 0.117* | |
C27 | 0.3003 (6) | −0.0335 (4) | 0.93352 (11) | 0.0897 (13) | |
H27 | 0.3980 | −0.0754 | 0.9360 | 0.108* | |
C28 | 0.2308 (5) | −0.0138 (3) | 0.89762 (9) | 0.0654 (9) | |
C29 | 0.3806 (5) | −0.0007 (3) | 0.83978 (10) | 0.0622 (9) | |
C30 | 0.4572 (5) | 0.0987 (3) | 0.84743 (12) | 0.0740 (11) | |
H30 | 0.4622 | 0.1241 | 0.8721 | 0.089* | |
C31 | 0.5255 (5) | 0.1595 (4) | 0.81873 (14) | 0.0855 (12) | |
H31 | 0.5752 | 0.2264 | 0.8241 | 0.103* | |
C32 | 0.5207 (5) | 0.1220 (4) | 0.78195 (14) | 0.0827 (12) | |
H32 | 0.5661 | 0.1639 | 0.7625 | 0.099* | |
C33 | 0.4486 (4) | 0.0224 (3) | 0.77414 (10) | 0.0661 (9) | |
C34 | 0.4460 (5) | −0.0202 (4) | 0.73636 (12) | 0.0807 (12) | |
C35 | 0.3780 (4) | −0.0403 (3) | 0.80310 (10) | 0.0586 (9) | |
C36 | 0.3035 (5) | −0.1449 (4) | 0.79493 (10) | 0.0683 (10) | |
C37 | 1.108 (2) | 0.6227 (16) | 0.9599 (5) | 0.378 (18) | |
H37 | 1.2131 | 0.6350 | 0.9710 | 0.454* | |
C38 | 1.0635 (19) | 0.5159 (13) | 0.9502 (3) | 0.274 (10) | |
H38 | 1.1383 | 0.4580 | 0.9533 | 0.329* | |
C39 | 0.902 (2) | 0.5017 (9) | 0.9357 (2) | 0.195 (4) | |
H39 | 0.8636 | 0.4330 | 0.9288 | 0.235* | |
C40 | 0.7992 (11) | 0.5927 (14) | 0.9319 (2) | 0.182 (5) | |
H40 | 0.6924 | 0.5807 | 0.9216 | 0.218* | |
C41 | 0.837 (2) | 0.6995 (12) | 0.9418 (3) | 0.305 (11) | |
H41 | 0.7594 | 0.7566 | 0.9404 | 0.366* | |
C42 | 1.002 (2) | 0.7105 (13) | 0.9537 (5) | 0.356 (15) | |
H42 | 1.0442 | 0.7802 | 0.9578 | 0.427* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0771 (16) | 0.0471 (14) | 0.0762 (14) | −0.0046 (13) | −0.0215 (13) | 0.0079 (11) |
O2 | 0.0922 (19) | 0.0613 (15) | 0.0675 (14) | 0.0211 (15) | 0.0058 (14) | 0.0068 (12) |
N1 | 0.114 (4) | 0.094 (3) | 0.253 (7) | −0.037 (3) | −0.053 (4) | 0.031 (3) |
N2 | 0.102 (3) | 0.089 (3) | 0.137 (3) | 0.009 (2) | −0.053 (3) | −0.006 (2) |
N3 | 0.106 (3) | 0.157 (4) | 0.077 (2) | 0.013 (3) | 0.005 (2) | 0.006 (3) |
N4 | 0.108 (3) | 0.079 (3) | 0.095 (2) | −0.011 (2) | 0.016 (2) | −0.014 (2) |
C1 | 0.090 (3) | 0.067 (3) | 0.138 (4) | −0.015 (3) | −0.021 (3) | 0.018 (3) |
C2 | 0.062 (2) | 0.053 (2) | 0.088 (2) | −0.009 (2) | −0.003 (2) | 0.0094 (19) |
C3 | 0.075 (3) | 0.052 (2) | 0.103 (3) | 0.004 (2) | −0.005 (2) | 0.010 (2) |
C4 | 0.062 (2) | 0.061 (3) | 0.100 (3) | 0.007 (2) | −0.007 (2) | 0.006 (2) |
C5 | 0.056 (2) | 0.052 (2) | 0.089 (2) | −0.0064 (18) | −0.0048 (19) | 0.0024 (18) |
C6 | 0.063 (2) | 0.046 (2) | 0.0638 (18) | −0.0059 (18) | −0.0045 (17) | 0.0084 (15) |
C7 | 0.058 (2) | 0.054 (2) | 0.0645 (19) | −0.0009 (18) | −0.0020 (17) | 0.0079 (16) |
C8 | 0.068 (3) | 0.061 (2) | 0.089 (3) | −0.004 (2) | −0.020 (2) | −0.001 (2) |
C9 | 0.0576 (19) | 0.0480 (19) | 0.0544 (16) | −0.0002 (17) | −0.0076 (15) | 0.0003 (15) |
C10 | 0.073 (2) | 0.062 (2) | 0.0535 (18) | 0.003 (2) | 0.0001 (17) | 0.0139 (17) |
C11 | 0.073 (2) | 0.075 (3) | 0.0467 (16) | 0.020 (2) | −0.0031 (17) | 0.0000 (18) |
C12 | 0.0531 (19) | 0.061 (2) | 0.0572 (18) | 0.0127 (17) | −0.0047 (15) | −0.0109 (17) |
C13 | 0.067 (2) | 0.071 (3) | 0.082 (2) | 0.016 (2) | −0.011 (2) | −0.028 (2) |
C14 | 0.065 (3) | 0.073 (3) | 0.123 (4) | 0.007 (2) | −0.014 (3) | −0.040 (3) |
C15 | 0.063 (2) | 0.054 (2) | 0.121 (3) | −0.001 (2) | 0.007 (2) | −0.011 (2) |
C16 | 0.067 (2) | 0.050 (2) | 0.079 (2) | 0.0003 (19) | 0.0049 (19) | −0.0025 (18) |
C17 | 0.0512 (18) | 0.0486 (19) | 0.0582 (17) | 0.0077 (17) | 0.0021 (15) | −0.0021 (15) |
C18 | 0.0578 (19) | 0.0446 (18) | 0.0446 (14) | 0.0023 (16) | −0.0006 (14) | 0.0032 (13) |
C19 | 0.067 (2) | 0.0468 (19) | 0.0503 (16) | 0.0005 (17) | −0.0054 (15) | 0.0030 (14) |
C20 | 0.071 (2) | 0.059 (2) | 0.0529 (18) | −0.0005 (19) | 0.0007 (17) | 0.0012 (15) |
C21 | 0.083 (3) | 0.083 (3) | 0.064 (2) | 0.009 (2) | −0.001 (2) | −0.002 (2) |
C22 | 0.110 (4) | 0.114 (4) | 0.081 (3) | 0.030 (3) | 0.022 (3) | −0.008 (3) |
C23 | 0.149 (5) | 0.119 (4) | 0.070 (3) | 0.014 (4) | 0.024 (3) | −0.018 (3) |
C24 | 0.134 (4) | 0.104 (4) | 0.055 (2) | 0.006 (4) | −0.003 (3) | −0.009 (2) |
C25 | 0.100 (3) | 0.070 (2) | 0.0513 (19) | −0.003 (2) | −0.006 (2) | −0.0010 (17) |
C26 | 0.128 (4) | 0.110 (4) | 0.055 (2) | 0.014 (3) | −0.023 (2) | 0.007 (2) |
C27 | 0.100 (3) | 0.100 (3) | 0.070 (2) | 0.032 (3) | −0.017 (2) | 0.014 (2) |
C28 | 0.084 (2) | 0.057 (2) | 0.0544 (18) | 0.012 (2) | −0.0060 (18) | 0.0039 (16) |
C29 | 0.056 (2) | 0.062 (2) | 0.069 (2) | 0.0143 (19) | −0.0002 (17) | 0.0036 (18) |
C30 | 0.061 (2) | 0.069 (3) | 0.092 (3) | 0.003 (2) | −0.002 (2) | −0.011 (2) |
C31 | 0.061 (2) | 0.075 (3) | 0.120 (4) | −0.001 (2) | 0.008 (2) | −0.010 (3) |
C32 | 0.061 (2) | 0.078 (3) | 0.110 (3) | 0.005 (2) | 0.018 (2) | 0.025 (3) |
C33 | 0.0502 (19) | 0.070 (3) | 0.078 (2) | 0.010 (2) | 0.0092 (18) | 0.0082 (19) |
C34 | 0.065 (2) | 0.104 (3) | 0.073 (3) | 0.010 (3) | 0.007 (2) | 0.018 (2) |
C35 | 0.0469 (18) | 0.058 (2) | 0.071 (2) | 0.0127 (17) | 0.0007 (16) | 0.0024 (17) |
C36 | 0.062 (2) | 0.072 (3) | 0.072 (2) | 0.010 (2) | 0.0113 (19) | −0.002 (2) |
C37 | 0.31 (2) | 0.63 (5) | 0.191 (13) | −0.13 (3) | −0.031 (15) | −0.10 (2) |
C38 | 0.245 (17) | 0.47 (3) | 0.105 (7) | 0.145 (18) | 0.020 (8) | 0.034 (10) |
C39 | 0.250 (13) | 0.258 (13) | 0.079 (5) | −0.030 (11) | 0.047 (7) | 0.017 (6) |
C40 | 0.136 (6) | 0.299 (14) | 0.110 (5) | 0.025 (9) | 0.008 (4) | 0.070 (8) |
C41 | 0.36 (2) | 0.41 (2) | 0.141 (8) | −0.238 (19) | 0.027 (10) | 0.055 (11) |
C42 | 0.33 (3) | 0.52 (4) | 0.218 (16) | −0.25 (3) | 0.038 (17) | −0.064 (19) |
O1—C6 | 1.374 (4) | C20—C21 | 1.406 (6) |
O1—C9 | 1.387 (4) | C20—C25 | 1.415 (5) |
O2—C29 | 1.361 (4) | C21—C22 | 1.367 (6) |
O2—C28 | 1.401 (4) | C21—H21 | 0.9300 |
N1—C1 | 1.153 (6) | C22—C23 | 1.395 (7) |
N2—C8 | 1.140 (5) | C22—H22 | 0.9300 |
N3—C34 | 1.139 (5) | C23—C24 | 1.336 (7) |
N4—C36 | 1.138 (5) | C23—H23 | 0.9300 |
C1—C2 | 1.421 (6) | C24—C25 | 1.407 (6) |
C2—C3 | 1.379 (5) | C24—H24 | 0.9300 |
C2—C7 | 1.402 (5) | C25—C26 | 1.419 (7) |
C3—C4 | 1.364 (6) | C26—C27 | 1.352 (6) |
C3—H3 | 0.9300 | C26—H26 | 0.9300 |
C4—C5 | 1.386 (5) | C27—C28 | 1.404 (5) |
C4—H4 | 0.9300 | C27—H27 | 0.9300 |
C5—C6 | 1.374 (5) | C29—C35 | 1.386 (5) |
C5—H5 | 0.9300 | C29—C30 | 1.389 (5) |
C6—C7 | 1.390 (5) | C30—C31 | 1.371 (6) |
C7—C8 | 1.431 (6) | C30—H30 | 0.9300 |
C9—C18 | 1.370 (4) | C31—C32 | 1.381 (6) |
C9—C10 | 1.405 (4) | C31—H31 | 0.9300 |
C10—C11 | 1.353 (5) | C32—C33 | 1.378 (6) |
C10—H10 | 0.9300 | C32—H32 | 0.9300 |
C11—C12 | 1.411 (5) | C33—C35 | 1.398 (5) |
C11—H11 | 0.9300 | C33—C34 | 1.436 (6) |
C12—C13 | 1.409 (5) | C35—C36 | 1.442 (6) |
C12—C17 | 1.421 (4) | C37—C42 | 1.382 (10) |
C13—C14 | 1.348 (6) | C37—C38 | 1.400 (9) |
C13—H13 | 0.9300 | C37—H37 | 0.9300 |
C14—C15 | 1.407 (6) | C38—C39 | 1.381 (9) |
C14—H14 | 0.9300 | C38—H38 | 0.9300 |
C15—C16 | 1.352 (5) | C39—C40 | 1.388 (8) |
C15—H15 | 0.9300 | C39—H39 | 0.9300 |
C16—C17 | 1.419 (5) | C40—C41 | 1.390 (9) |
C16—H16 | 0.9300 | C40—H40 | 0.9300 |
C17—C18 | 1.421 (4) | C41—C42 | 1.375 (9) |
C18—C19 | 1.495 (4) | C41—H41 | 0.9300 |
C19—C28 | 1.373 (5) | C42—H42 | 0.9300 |
C19—C20 | 1.425 (5) | ||
C6—O1—C9 | 121.5 (3) | C20—C21—H21 | 119.8 |
C29—O2—C28 | 118.1 (3) | C21—C22—C23 | 120.4 (5) |
N1—C1—C2 | 179.7 (6) | C21—C22—H22 | 119.8 |
C3—C2—C7 | 120.4 (4) | C23—C22—H22 | 119.8 |
C3—C2—C1 | 120.3 (4) | C24—C23—C22 | 120.5 (4) |
C7—C2—C1 | 119.3 (4) | C24—C23—H23 | 119.7 |
C4—C3—C2 | 119.6 (4) | C22—C23—H23 | 119.7 |
C4—C3—H3 | 120.2 | C23—C24—C25 | 121.3 (4) |
C2—C3—H3 | 120.2 | C23—C24—H24 | 119.4 |
C3—C4—C5 | 121.2 (4) | C25—C24—H24 | 119.4 |
C3—C4—H4 | 119.4 | C24—C25—C20 | 118.8 (4) |
C5—C4—H4 | 119.4 | C24—C25—C26 | 122.2 (4) |
C6—C5—C4 | 119.4 (4) | C20—C25—C26 | 119.0 (4) |
C6—C5—H5 | 120.3 | C27—C26—C25 | 120.9 (4) |
C4—C5—H5 | 120.3 | C27—C26—H26 | 119.5 |
C5—C6—O1 | 124.2 (3) | C25—C26—H26 | 119.5 |
C5—C6—C7 | 120.5 (3) | C26—C27—C28 | 119.6 (4) |
O1—C6—C7 | 115.2 (3) | C26—C27—H27 | 120.2 |
C6—C7—C2 | 118.8 (3) | C28—C27—H27 | 120.2 |
C6—C7—C8 | 120.2 (3) | C19—C28—O2 | 120.6 (3) |
C2—C7—C8 | 121.0 (3) | C19—C28—C27 | 122.6 (3) |
N2—C8—C7 | 178.0 (5) | O2—C28—C27 | 116.7 (3) |
C18—C9—O1 | 116.4 (3) | O2—C29—C35 | 116.9 (3) |
C18—C9—C10 | 122.1 (3) | O2—C29—C30 | 123.2 (3) |
O1—C9—C10 | 121.0 (3) | C35—C29—C30 | 119.8 (3) |
C11—C10—C9 | 119.4 (3) | C31—C30—C29 | 120.4 (4) |
C11—C10—H10 | 120.3 | C31—C30—H30 | 119.8 |
C9—C10—H10 | 120.3 | C29—C30—H30 | 119.8 |
C10—C11—C12 | 121.4 (3) | C30—C31—C32 | 120.4 (4) |
C10—C11—H11 | 119.3 | C30—C31—H31 | 119.8 |
C12—C11—H11 | 119.3 | C32—C31—H31 | 119.8 |
C13—C12—C11 | 122.1 (3) | C33—C32—C31 | 119.8 (4) |
C13—C12—C17 | 119.2 (4) | C33—C32—H32 | 120.1 |
C11—C12—C17 | 118.6 (3) | C31—C32—H32 | 120.1 |
C14—C13—C12 | 120.7 (4) | C32—C33—C35 | 120.4 (4) |
C14—C13—H13 | 119.6 | C32—C33—C34 | 121.1 (4) |
C12—C13—H13 | 119.6 | C35—C33—C34 | 118.5 (4) |
C13—C14—C15 | 120.5 (4) | N3—C34—C33 | 178.5 (5) |
C13—C14—H14 | 119.8 | C29—C35—C33 | 119.2 (4) |
C15—C14—H14 | 119.8 | C29—C35—C36 | 120.4 (3) |
C16—C15—C14 | 120.6 (4) | C33—C35—C36 | 120.4 (3) |
C16—C15—H15 | 119.7 | N4—C36—C35 | 177.6 (4) |
C14—C15—H15 | 119.7 | C42—C37—C38 | 122.8 (12) |
C15—C16—C17 | 120.8 (4) | C42—C37—H37 | 118.6 |
C15—C16—H16 | 119.6 | C38—C37—H37 | 118.6 |
C17—C16—H16 | 119.6 | C39—C38—C37 | 116.0 (10) |
C16—C17—C12 | 118.1 (3) | C39—C38—H38 | 122.0 |
C16—C17—C18 | 122.3 (3) | C37—C38—H38 | 122.0 |
C12—C17—C18 | 119.6 (3) | C38—C39—C40 | 118.2 (9) |
C9—C18—C17 | 118.5 (3) | C38—C39—H39 | 120.9 |
C9—C18—C19 | 120.4 (3) | C40—C39—H39 | 120.9 |
C17—C18—C19 | 120.9 (3) | C39—C40—C41 | 127.8 (9) |
C28—C19—C20 | 118.1 (3) | C39—C40—H40 | 116.1 |
C28—C19—C18 | 119.1 (3) | C41—C40—H40 | 116.1 |
C20—C19—C18 | 122.8 (3) | C42—C41—C40 | 111.8 (10) |
C21—C20—C25 | 118.6 (3) | C42—C41—H41 | 124.1 |
C21—C20—C19 | 121.6 (3) | C40—C41—H41 | 124.1 |
C25—C20—C19 | 119.8 (4) | C41—C42—C37 | 122.9 (12) |
C22—C21—C20 | 120.4 (4) | C41—C42—H42 | 118.5 |
C22—C21—H21 | 119.8 | C37—C42—H42 | 118.5 |
N1—C1—C2—C3 | −175 (100) | C18—C19—C20—C21 | 2.5 (5) |
N1—C1—C2—C7 | 5 (99) | C28—C19—C20—C25 | 1.2 (5) |
C7—C2—C3—C4 | 1.1 (6) | C18—C19—C20—C25 | −178.1 (3) |
C1—C2—C3—C4 | −179.2 (4) | C25—C20—C21—C22 | 0.3 (6) |
C2—C3—C4—C5 | −2.6 (6) | C19—C20—C21—C22 | 179.7 (4) |
C3—C4—C5—C6 | 1.1 (6) | C20—C21—C22—C23 | 0.1 (7) |
C4—C5—C6—O1 | 178.5 (3) | C21—C22—C23—C24 | 0.1 (8) |
C4—C5—C6—C7 | 2.0 (6) | C22—C23—C24—C25 | −0.8 (8) |
C9—O1—C6—C5 | 29.3 (5) | C23—C24—C25—C20 | 1.1 (7) |
C9—O1—C6—C7 | −154.0 (3) | C23—C24—C25—C26 | −178.8 (5) |
C5—C6—C7—C2 | −3.5 (5) | C21—C20—C25—C24 | −0.9 (6) |
O1—C6—C7—C2 | 179.7 (3) | C19—C20—C25—C24 | 179.7 (4) |
C5—C6—C7—C8 | 174.3 (3) | C21—C20—C25—C26 | 179.1 (4) |
O1—C6—C7—C8 | −2.5 (5) | C19—C20—C25—C26 | −0.3 (6) |
C3—C2—C7—C6 | 1.9 (6) | C24—C25—C26—C27 | 179.3 (5) |
C1—C2—C7—C6 | −177.8 (4) | C20—C25—C26—C27 | −0.7 (7) |
C3—C2—C7—C8 | −175.8 (4) | C25—C26—C27—C28 | 0.8 (7) |
C1—C2—C7—C8 | 4.4 (6) | C20—C19—C28—O2 | 175.5 (3) |
C6—C7—C8—N2 | −135 (14) | C18—C19—C28—O2 | −5.1 (5) |
C2—C7—C8—N2 | 43 (14) | C20—C19—C28—C27 | −1.1 (6) |
C6—O1—C9—C18 | −148.6 (3) | C18—C19—C28—C27 | 178.2 (4) |
C6—O1—C9—C10 | 38.8 (5) | C29—O2—C28—C19 | 65.2 (5) |
C18—C9—C10—C11 | 2.1 (5) | C29—O2—C28—C27 | −117.9 (4) |
O1—C9—C10—C11 | 174.3 (3) | C26—C27—C28—C19 | 0.2 (7) |
C9—C10—C11—C12 | 2.4 (6) | C26—C27—C28—O2 | −176.6 (4) |
C10—C11—C12—C13 | 176.1 (3) | C28—O2—C29—C35 | −147.4 (3) |
C10—C11—C12—C17 | −2.6 (5) | C28—O2—C29—C30 | 34.6 (5) |
C11—C12—C13—C14 | −175.5 (4) | O2—C29—C30—C31 | −179.9 (3) |
C17—C12—C13—C14 | 3.1 (5) | C35—C29—C30—C31 | 2.1 (5) |
C12—C13—C14—C15 | −1.2 (6) | C29—C30—C31—C32 | −0.8 (6) |
C13—C14—C15—C16 | −1.5 (6) | C30—C31—C32—C33 | −0.7 (6) |
C14—C15—C16—C17 | 2.1 (6) | C31—C32—C33—C35 | 1.0 (6) |
C15—C16—C17—C12 | −0.1 (5) | C31—C32—C33—C34 | −178.3 (4) |
C15—C16—C17—C18 | 177.6 (3) | C32—C33—C34—N3 | 141 (18) |
C13—C12—C17—C16 | −2.5 (5) | C35—C33—C34—N3 | −38 (19) |
C11—C12—C17—C16 | 176.2 (3) | O2—C29—C35—C33 | −180.0 (3) |
C13—C12—C17—C18 | 179.8 (3) | C30—C29—C35—C33 | −1.8 (5) |
C11—C12—C17—C18 | −1.5 (5) | O2—C29—C35—C36 | 0.0 (5) |
O1—C9—C18—C17 | −178.6 (3) | C30—C29—C35—C36 | 178.1 (3) |
C10—C9—C18—C17 | −6.1 (5) | C32—C33—C35—C29 | 0.3 (5) |
O1—C9—C18—C19 | −3.8 (5) | C34—C33—C35—C29 | 179.5 (3) |
C10—C9—C18—C19 | 168.7 (3) | C32—C33—C35—C36 | −179.6 (3) |
C16—C17—C18—C9 | −171.9 (3) | C34—C33—C35—C36 | −0.4 (5) |
C12—C17—C18—C9 | 5.7 (5) | C29—C35—C36—N4 | −161 (11) |
C16—C17—C18—C19 | 13.3 (5) | C33—C35—C36—N4 | 19 (12) |
C12—C17—C18—C19 | −169.0 (3) | C42—C37—C38—C39 | −3 (2) |
C9—C18—C19—C28 | −101.1 (4) | C37—C38—C39—C40 | 0.3 (10) |
C17—C18—C19—C28 | 73.6 (4) | C38—C39—C40—C41 | −1.5 (13) |
C9—C18—C19—C20 | 78.2 (4) | C39—C40—C41—C42 | 5.3 (17) |
C17—C18—C19—C20 | −107.1 (4) | C40—C41—C42—C37 | −8 (3) |
C28—C19—C20—C21 | −178.2 (4) | C38—C37—C42—C41 | 8 (3) |
Experimental details
Crystal data | |
Chemical formula | C36H18N4O2·C6H6 |
Mr | 616.65 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 295 |
a, b, c (Å) | 7.8783 (1), 12.2854 (2), 35.3968 (5) |
V (Å3) | 3425.99 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.16 × 0.12 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.979, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18358, 3821, 2647 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.149, 1.04 |
No. of reflections | 3821 |
No. of parameters | 433 |
No. of restraints | 15 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.15 |
Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1998), SHELXTL (Bruker, 2001).
(R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl as well as its derivative chiral non-entrosymmetrically phthalocyanines play an important role in the molecular self-assembly and molecular recognition in chemical, physical and biological sciences, since can form metal complexes with rare earth, actinide, and some early transition metals and main-group elements. (Kobayashi et al., 1999: Buchler & Ng, 2000).
To date, a variety of chiral supramolecular architectures have been obtained based on the above mentioned multifunctional ligands (Jiang & Lin, 2006). More recently, two novel interlocked chiral nanotubes formed from Ni(acac)2 and C2-symmetric 1,1-binaphthyl-6,6'-bipyridines have been reported (Jiang & Lin, 2003). They pointed out that the twisted binding sites of chiral rigid ditopic bridging ligands based on the 1,1'-binaphthyl unit will induce the formation of helical structures when linked by a linear metal-connecting point. Herein, we report the synthesis and crystal structure of a chiral organic compound (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl benzene solvate (I).
The molecular structure of (I) is shown in Fig. 1. The cyano group C—N bond distances in this compound range from 1.138 (5) to 1.153 (6) Å and are similar to those in inorganic coordinated complexes (Ni, Kou, Zhang et al., 2005; Ni, Kou, Zhao et al., 2005). The C18—C19 bond distance is 1.495 (4) Å. The ten carbon atoms from two naphthyl rings in the title compound, respectively, are almost coplanar with the largest deviation value of 0.0527 (5) Å and 0.0138 (5) Å from the mean plane. The dihedral angle between the two naphthyl rings is 79.5 (5)°, which are similar to that of its derivative (R)-3,3'-Dibromo-2,2'-dimethoxy-5,5',6,6',7,7',8,8'-octahydro-1,1'- binaphthalene (80.2 (3)°) (He & Ng, 2006) and significantly larger than that of (R)-3,3'-Bis(3,4,5-trifluorophenyl)-1,1'-binaphthalene-2,2'-diol (73.5 (1)°) (Kang et al., 2007) due to steric effects.
In (I), the (R)-(+)-2,2'-Bis(2,3-dicyanophenyl)-1,1'-binaphthyl units are connected together by the intermolecular π–π interactions leading to chiral helical one-dimensional supramolecular structures as shown in Fig. 2.