
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027596/im2019sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027596/im2019Isup2.hkl |
CCDC reference: 654950
Racemic 1,1'-binaphthyl-2,2'-diol (0.286 g, 1 mmol) and 4-(bromomethyl)benzonitrile (0.392 g, 2 mmol) were dissolved in acetone (25 ml) in the presence of K2CO3 (0.138 g, 1 mmol) and refluxed for 3 days. After the mixture was cooled to room temperature, the solution was filtered and rotated in vacuum affording a white precipitate of compound (I). Colourless crystals of the title compound suitable for X-ray diffraction were obtained from a solution of 100 mg (I) in 15 ml diethylether after 3 weeks.
All the C—H hydrogen atoms were generated geometrically and with C—H distances ranging from 0.93 to 0.97 Å and included in the refinement in riding motion approximation with Uiso = 1.2Ueq of the carrier atom.
Because of their highly stable chiral configuration, the 2,2-substituted 1,1-binaphthyls have been extensively used to control many asymmetric processes and have demonstrated outstanding chiral discrimination properties (Pu, 1998). Most 1,1-binaphthyl molecules are C2 symmetric with two identical naphthyl units. The rigid structure and the C2 symmetry of the chiral binaphthyl molecules play an important role in chiral induction (Minatti & Dötz, 2005; Hiroshi, et al., 2005). Herein we report the 1,1'-binaphthyl derivative shown below (I) and its crystal structure.
The crystal data show that in the title compound, C36H24N2O2, the two naphthyl rings are approximately perpendicular to each other and the dihedral angle is 86.68 (3)°. Nevertheless, the two 4-cyanobenzyloxy rings are almost parallel with respect to each other with a dihedral angle of 10.33 (8)°. In Fig. 2, Cg1 and Cg2 are the centroids of ring A (C30—C35) and ring B (C22—C27), respectively. The centroid distance for Cg1—Cg2ii is 3.835 (3) Å, indicating quite strong π-π interactions between the neighbouring molecules. The face to face π-π interactions between the phenyl rings of neighbouring molecules play a very important function in stabilizing the crystal structure. The one-dimensional chain structure is formed by stacking of molecules showing the same absolute configuration via π-π interactions along the a axis. (symmetry code: (i) 1 + x,y,z; (ii) -1 + x,y,z)
For related literature, see: Hiroshi et al. (2005); Minatti & Dötz (2005); Pu (1998).
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C36H24N2O2 | Z = 2 |
Mr = 516.57 | F(000) = 540 |
Triclinic, P1 | Dx = 1.273 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.835 (1) Å | Cell parameters from 3754 reflections |
b = 10.112 (1) Å | θ = 2.1–22.0° |
c = 17.864 (2) Å | µ = 0.08 mm−1 |
α = 104.696 (2)° | T = 291 K |
β = 91.999 (2)° | Block, colourless |
γ = 98.995 (3)° | 0.30 × 0.26 × 0.24 mm |
V = 1348.0 (3) Å3 |
Bruker SMART APEX CCD diffractometer | 5312 independent reflections |
Radiation source: sealed tube | 4098 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 26.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→9 |
Tmin = 0.97, Tmax = 0.98 | k = −12→12 |
12114 measured reflections | l = −22→22 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.04P)2 + 0.33P] where P = (Fo2 + 2Fc2)/3 |
5312 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C36H24N2O2 | γ = 98.995 (3)° |
Mr = 516.57 | V = 1348.0 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.835 (1) Å | Mo Kα radiation |
b = 10.112 (1) Å | µ = 0.08 mm−1 |
c = 17.864 (2) Å | T = 291 K |
α = 104.696 (2)° | 0.30 × 0.26 × 0.24 mm |
β = 91.999 (2)° |
Bruker SMART APEX CCD diffractometer | 5312 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 4098 reflections with I > 2σ(I) |
Tmin = 0.97, Tmax = 0.98 | Rint = 0.033 |
12114 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.112 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.13 e Å−3 |
5312 reflections | Δρmin = −0.16 e Å−3 |
361 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.1647 (0.0015) x - 3.8763 (0.0051) y + 6.1389 (0.0071) z = 2.8650 (0.0046) * 0.0056 (0.0016) C1 * -0.0023 (0.0017) C2 * -0.0187 (0.0015) C3 * -0.0022 (0.0015) C4 * 0.0187 (0.0015) C5 * 0.0019 (0.0016) C6 * -0.0008 (0.0018) C7 * -0.0149 (0.0016) C8 * -0.0050 (0.0016) C9 * 0.0177 (0.0016) C10 Rms deviation of fitted atoms = 0.0114 - 3.5151 (0.0024) x - 6.1219 (0.0043) y + 13.3947 (0.0063) z = 3.2425 (0.0024) Angle to previous plane (with approximate e.s.d.) = 86.68 (0.03) * -0.0245 (0.0015) C11 * 0.0118 (0.0015) C12 * 0.0277 (0.0016) C13 * -0.0005 (0.0016) C14 * -0.0134 (0.0018) C15 * -0.0233 (0.0015) C16 * 0.0078 (0.0015) C17 * 0.0303 (0.0015) C18 * 0.0004 (0.0015) C19 * -0.0164 (0.0017) C20 Rms deviation of fitted atoms = 0.0187 - 7.0702 (0.0028) x + 5.5597 (0.0069) y - 3.4434 (0.0131) z = 1.4634 (0.0020) Angle to previous plane (with approximate e.s.d.) = 86.97 (0.04) * 0.0025 (0.0013) C30 * 0.0009 (0.0013) C31 * -0.0039 (0.0014) C32 * 0.0034 (0.0013) C33 * 0.0000 (0.0014) C34 * -0.0030 (0.0013) C35 Rms deviation of fitted atoms = 0.0027 7.1892 (0.0026) x - 4.4575 (0.0072) y + 5.3099 (0.0132) z = 2.6051 (0.0034) Angle to previous plane (with approximate e.s.d.) = 10.33 (0.08) * -0.0098 (0.0014) C22 * 0.0074 (0.0014) C23 * 0.0030 (0.0013) C24 * -0.0110 (0.0013) C25 * 0.0087 (0.0013) C26 * 0.0017 (0.0014) C27 Rms deviation of fitted atoms = 0.0077 |
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 | ||
C1 | 0.2017 (3) | 0.29019 (19) | 0.41549 (11) | 0.0433 (4) | |
C2 | 0.1441 (2) | 0.30558 (19) | 0.49104 (11) | 0.0426 (4) | |
C3 | 0.0597 (2) | 0.19262 (19) | 0.51564 (11) | 0.0411 (4) | |
H3 | 0.0386 | 0.1048 | 0.4811 | 0.049* | |
C4 | 0.0081 (2) | 0.20905 (19) | 0.58890 (10) | 0.0389 (4) | |
H4 | −0.0466 | 0.1326 | 0.6041 | 0.047* | |
C5 | 0.0369 (2) | 0.33958 (19) | 0.64112 (11) | 0.0398 (4) | |
H5 | 0.0030 | 0.3500 | 0.6914 | 0.048* | |
C6 | 0.1142 (2) | 0.4520 (2) | 0.61907 (11) | 0.0451 (4) | |
H6 | 0.1300 | 0.5391 | 0.6541 | 0.054* | |
C7 | 0.1709 (3) | 0.4387 (2) | 0.54415 (12) | 0.0455 (4) | |
C8 | 0.2511 (2) | 0.5520 (2) | 0.51978 (12) | 0.0465 (5) | |
H8 | 0.2671 | 0.6401 | 0.5540 | 0.056* | |
C9 | 0.3061 (3) | 0.5372 (2) | 0.44789 (11) | 0.0467 (5) | |
H9 | 0.3594 | 0.6142 | 0.4328 | 0.056* | |
C10 | 0.2822 (3) | 0.4056 (2) | 0.39633 (11) | 0.0462 (5) | |
C11 | 0.1844 (2) | 0.15117 (19) | 0.35772 (10) | 0.0398 (4) | |
C12 | 0.0469 (2) | 0.10386 (19) | 0.30272 (10) | 0.0399 (4) | |
C13 | 0.0371 (2) | −0.01979 (19) | 0.24483 (11) | 0.0432 (4) | |
H13 | −0.0579 | −0.0499 | 0.2084 | 0.052* | |
C14 | 0.1651 (2) | −0.0958 (2) | 0.24160 (11) | 0.0432 (4) | |
H14 | 0.1586 | −0.1768 | 0.2020 | 0.052* | |
C15 | 0.3073 (2) | −0.0546 (2) | 0.29676 (11) | 0.0441 (4) | |
C16 | 0.4430 (2) | −0.1339 (2) | 0.29537 (11) | 0.0442 (4) | |
H16 | 0.4398 | −0.2143 | 0.2557 | 0.053* | |
C17 | 0.5746 (2) | −0.0945 (2) | 0.35025 (11) | 0.0434 (4) | |
H17 | 0.6609 | −0.1485 | 0.3487 | 0.052* | |
C18 | 0.5836 (2) | 0.0262 (2) | 0.40949 (11) | 0.0425 (4) | |
H18 | 0.6751 | 0.0515 | 0.4477 | 0.051* | |
C19 | 0.4591 (2) | 0.1089 (2) | 0.41237 (11) | 0.0437 (4) | |
H19 | 0.4689 | 0.1908 | 0.4516 | 0.052* | |
C20 | 0.3159 (2) | 0.0704 (2) | 0.35593 (11) | 0.0430 (4) | |
C21 | 0.4282 (2) | 0.47657 (19) | 0.29425 (11) | 0.0413 (4) | |
H21A | 0.5379 | 0.5130 | 0.3250 | 0.050* | |
H21B | 0.3654 | 0.5527 | 0.2964 | 0.050* | |
C22 | 0.4599 (3) | 0.4117 (2) | 0.21174 (11) | 0.0450 (4) | |
C23 | 0.5443 (2) | 0.4935 (2) | 0.16926 (11) | 0.0448 (4) | |
H23 | 0.5869 | 0.5866 | 0.1925 | 0.054* | |
C24 | 0.5663 (2) | 0.43691 (19) | 0.09120 (10) | 0.0387 (4) | |
H24 | 0.6232 | 0.4930 | 0.0626 | 0.046* | |
C25 | 0.5052 (2) | 0.29965 (18) | 0.05614 (10) | 0.0373 (4) | |
C26 | 0.4246 (2) | 0.2174 (2) | 0.09994 (11) | 0.0420 (4) | |
H26 | 0.3855 | 0.1235 | 0.0774 | 0.050* | |
C27 | 0.4018 (2) | 0.27383 (19) | 0.17680 (10) | 0.0408 (4) | |
H27 | 0.3461 | 0.2175 | 0.2055 | 0.049* | |
C28 | 0.5283 (2) | 0.24323 (19) | −0.02306 (10) | 0.0374 (4) | |
C29 | −0.2123 (2) | 0.15527 (18) | 0.24646 (10) | 0.0373 (4) | |
H29A | −0.3047 | 0.2070 | 0.2630 | 0.045* | |
H29B | −0.2607 | 0.0572 | 0.2339 | 0.045* | |
C30 | −0.1420 (2) | 0.19107 (19) | 0.17444 (10) | 0.0392 (4) | |
C31 | −0.0440 (2) | 0.3190 (2) | 0.18004 (11) | 0.0426 (4) | |
H31 | −0.0178 | 0.3826 | 0.2283 | 0.051* | |
C32 | 0.0161 (2) | 0.3539 (2) | 0.11436 (11) | 0.0448 (4) | |
H32 | 0.0831 | 0.4404 | 0.1191 | 0.054* | |
C33 | −0.0220 (2) | 0.26212 (19) | 0.04243 (11) | 0.0407 (4) | |
C34 | −0.1196 (2) | 0.1337 (2) | 0.03658 (12) | 0.0451 (5) | |
H34 | −0.1462 | 0.0701 | −0.0117 | 0.054* | |
C35 | −0.1781 (2) | 0.0996 (2) | 0.10237 (11) | 0.0442 (4) | |
H35 | −0.2435 | 0.0124 | 0.0977 | 0.053* | |
C36 | 0.0382 (2) | 0.29689 (18) | −0.02469 (11) | 0.0400 (4) | |
N1 | 0.5449 (2) | 0.19579 (17) | −0.08698 (9) | 0.0439 (4) | |
N2 | 0.0847 (2) | 0.32188 (16) | −0.08039 (9) | 0.0445 (4) | |
O1 | −0.07884 (15) | 0.18709 (13) | 0.30920 (7) | 0.0389 (3) | |
O2 | 0.33595 (18) | 0.38044 (13) | 0.32265 (7) | 0.0471 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0440 (10) | 0.0398 (10) | 0.0434 (10) | 0.0031 (8) | 0.0030 (8) | 0.0087 (8) |
C2 | 0.0454 (10) | 0.0367 (9) | 0.0446 (11) | 0.0094 (8) | 0.0047 (8) | 0.0073 (8) |
C3 | 0.0424 (10) | 0.0422 (10) | 0.0401 (10) | 0.0133 (8) | 0.0141 (8) | 0.0083 (8) |
C4 | 0.0397 (9) | 0.0431 (10) | 0.0386 (9) | 0.0126 (8) | 0.0180 (7) | 0.0138 (8) |
C5 | 0.0382 (9) | 0.0442 (10) | 0.0398 (10) | 0.0152 (8) | 0.0226 (8) | 0.0088 (8) |
C6 | 0.0414 (10) | 0.0412 (10) | 0.0494 (11) | 0.0102 (8) | 0.0146 (8) | 0.0029 (8) |
C7 | 0.0477 (11) | 0.0373 (10) | 0.0481 (11) | 0.0087 (8) | 0.0060 (8) | 0.0036 (8) |
C8 | 0.0438 (10) | 0.0374 (10) | 0.0520 (12) | 0.0035 (8) | 0.0054 (9) | 0.0020 (8) |
C9 | 0.0473 (11) | 0.0384 (10) | 0.0496 (11) | −0.0026 (8) | 0.0036 (9) | 0.0087 (8) |
C10 | 0.0486 (11) | 0.0419 (10) | 0.0431 (11) | −0.0035 (8) | 0.0080 (8) | 0.0082 (8) |
C11 | 0.0402 (10) | 0.0414 (10) | 0.0389 (10) | 0.0067 (8) | 0.0097 (8) | 0.0115 (8) |
C12 | 0.0379 (10) | 0.0437 (10) | 0.0396 (10) | 0.0129 (8) | 0.0048 (8) | 0.0100 (8) |
C13 | 0.0430 (10) | 0.0427 (10) | 0.0406 (10) | 0.0121 (8) | 0.0022 (8) | 0.0024 (8) |
C14 | 0.0426 (10) | 0.0428 (10) | 0.0431 (10) | 0.0132 (8) | 0.0068 (8) | 0.0053 (8) |
C15 | 0.0433 (10) | 0.0484 (11) | 0.0430 (10) | 0.0147 (9) | 0.0115 (8) | 0.0110 (8) |
C16 | 0.0417 (10) | 0.0500 (11) | 0.0456 (11) | 0.0190 (9) | 0.0168 (8) | 0.0124 (9) |
C17 | 0.0443 (10) | 0.0474 (11) | 0.0416 (10) | 0.0144 (8) | 0.0128 (8) | 0.0122 (8) |
C18 | 0.0427 (10) | 0.0466 (11) | 0.0403 (10) | 0.0083 (8) | 0.0019 (8) | 0.0148 (8) |
C19 | 0.0388 (10) | 0.0486 (11) | 0.0432 (10) | 0.0040 (8) | 0.0047 (8) | 0.0132 (8) |
C20 | 0.0400 (10) | 0.0452 (10) | 0.0445 (10) | 0.0064 (8) | 0.0095 (8) | 0.0128 (8) |
C21 | 0.0437 (10) | 0.0380 (10) | 0.0423 (10) | 0.0001 (8) | 0.0125 (8) | 0.0137 (8) |
C22 | 0.0477 (11) | 0.0413 (10) | 0.0444 (11) | 0.0014 (8) | 0.0122 (8) | 0.0110 (8) |
C23 | 0.0415 (10) | 0.0478 (11) | 0.0435 (10) | 0.0055 (8) | 0.0132 (8) | 0.0092 (8) |
C24 | 0.0381 (9) | 0.0427 (10) | 0.0412 (10) | 0.0144 (8) | 0.0169 (7) | 0.0153 (8) |
C25 | 0.0403 (9) | 0.0396 (9) | 0.0372 (9) | 0.0169 (8) | 0.0174 (7) | 0.0117 (7) |
C26 | 0.0419 (10) | 0.0416 (10) | 0.0409 (10) | 0.0074 (8) | 0.0158 (8) | 0.0061 (8) |
C27 | 0.0442 (10) | 0.0375 (9) | 0.0412 (10) | 0.0000 (8) | 0.0173 (8) | 0.0136 (8) |
C28 | 0.0417 (10) | 0.0419 (10) | 0.0386 (10) | 0.0210 (8) | 0.0202 (8) | 0.0182 (8) |
C29 | 0.0388 (9) | 0.0365 (9) | 0.0387 (9) | 0.0106 (7) | −0.0032 (7) | 0.0119 (7) |
C30 | 0.0368 (9) | 0.0406 (10) | 0.0395 (10) | 0.0100 (8) | −0.0065 (7) | 0.0086 (8) |
C31 | 0.0394 (10) | 0.0425 (10) | 0.0422 (10) | 0.0056 (8) | −0.0018 (8) | 0.0056 (8) |
C32 | 0.0423 (10) | 0.0420 (10) | 0.0444 (11) | −0.0030 (8) | 0.0023 (8) | 0.0074 (8) |
C33 | 0.0386 (10) | 0.0398 (10) | 0.0442 (10) | 0.0037 (8) | 0.0014 (8) | 0.0140 (8) |
C34 | 0.0411 (10) | 0.0424 (10) | 0.0466 (11) | 0.0018 (8) | −0.0051 (8) | 0.0067 (8) |
C35 | 0.0402 (10) | 0.0454 (10) | 0.0413 (10) | −0.0023 (8) | −0.0061 (8) | 0.0078 (8) |
C36 | 0.0389 (10) | 0.0361 (9) | 0.0451 (11) | −0.0039 (7) | −0.0013 (8) | 0.0176 (8) |
N1 | 0.0424 (9) | 0.0483 (9) | 0.0435 (9) | 0.0137 (7) | 0.0145 (7) | 0.0116 (7) |
N2 | 0.0427 (9) | 0.0409 (8) | 0.0438 (9) | −0.0164 (7) | 0.0056 (7) | 0.0139 (7) |
O1 | 0.0371 (7) | 0.0419 (7) | 0.0385 (7) | 0.0158 (5) | −0.0031 (5) | 0.0074 (5) |
O2 | 0.0547 (8) | 0.0389 (7) | 0.0438 (7) | −0.0111 (6) | 0.0130 (6) | 0.0139 (6) |
C1—C10 | 1.365 (3) | C19—C20 | 1.419 (3) |
C1—C2 | 1.417 (3) | C19—H19 | 0.9300 |
C1—C11 | 1.501 (3) | C21—O2 | 1.334 (2) |
C2—C3 | 1.405 (3) | C21—C22 | 1.500 (3) |
C2—C7 | 1.416 (3) | C21—H21A | 0.9700 |
C3—C4 | 1.361 (2) | C21—H21B | 0.9700 |
C3—H3 | 0.9300 | C22—C27 | 1.371 (3) |
C4—C5 | 1.390 (3) | C22—C23 | 1.371 (3) |
C4—H4 | 0.9300 | C23—C24 | 1.394 (3) |
C5—C6 | 1.357 (3) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—C25 | 1.371 (3) |
C6—C7 | 1.405 (3) | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | C25—C26 | 1.379 (2) |
C7—C8 | 1.395 (3) | C25—C28 | 1.414 (2) |
C8—C9 | 1.348 (3) | C26—C27 | 1.376 (2) |
C8—H8 | 0.9300 | C26—H26 | 0.9300 |
C9—C10 | 1.394 (3) | C27—H27 | 0.9300 |
C9—H9 | 0.9300 | C28—N1 | 1.141 (2) |
C10—O2 | 1.370 (2) | C29—O1 | 1.443 (2) |
C11—C12 | 1.372 (3) | C29—C30 | 1.521 (3) |
C11—C20 | 1.407 (3) | C29—H29A | 0.9700 |
C12—O1 | 1.382 (2) | C29—H29B | 0.9700 |
C12—C13 | 1.395 (3) | C30—C35 | 1.372 (3) |
C13—C14 | 1.350 (3) | C30—C31 | 1.375 (3) |
C13—H13 | 0.9300 | C31—C32 | 1.385 (3) |
C14—C15 | 1.399 (3) | C31—H31 | 0.9300 |
C14—H14 | 0.9300 | C32—C33 | 1.372 (3) |
C15—C20 | 1.418 (3) | C32—H32 | 0.9300 |
C15—C16 | 1.425 (3) | C33—C34 | 1.377 (3) |
C16—C17 | 1.337 (3) | C33—C36 | 1.409 (3) |
C16—H16 | 0.9300 | C34—C35 | 1.380 (3) |
C17—C18 | 1.389 (3) | C34—H34 | 0.9300 |
C17—H17 | 0.9300 | C35—H35 | 0.9300 |
C18—C19 | 1.374 (3) | C36—N2 | 1.145 (2) |
C18—H18 | 0.9300 | ||
C10—C1—C2 | 118.37 (17) | C20—C19—H19 | 119.7 |
C10—C1—C11 | 119.35 (17) | C11—C20—C15 | 120.10 (17) |
C2—C1—C11 | 122.22 (17) | C11—C20—C19 | 122.19 (18) |
C3—C2—C7 | 118.16 (17) | C15—C20—C19 | 117.71 (18) |
C3—C2—C1 | 122.21 (17) | O2—C21—C22 | 108.83 (15) |
C7—C2—C1 | 119.63 (17) | O2—C21—H21A | 109.9 |
C4—C3—C2 | 121.36 (18) | C22—C21—H21A | 109.9 |
C4—C3—H3 | 119.3 | O2—C21—H21B | 109.9 |
C2—C3—H3 | 119.3 | C22—C21—H21B | 109.9 |
C3—C4—C5 | 120.23 (17) | H21A—C21—H21B | 108.3 |
C3—C4—H4 | 119.9 | C27—C22—C23 | 119.03 (18) |
C5—C4—H4 | 119.9 | C27—C22—C21 | 121.88 (16) |
C6—C5—C4 | 120.26 (16) | C23—C22—C21 | 119.06 (17) |
C6—C5—H5 | 119.9 | C22—C23—C24 | 119.97 (18) |
C4—C5—H5 | 119.9 | C22—C23—H23 | 120.0 |
C5—C6—C7 | 121.08 (17) | C24—C23—H23 | 120.0 |
C5—C6—H6 | 119.5 | C25—C24—C23 | 120.77 (17) |
C7—C6—H6 | 119.5 | C25—C24—H24 | 119.6 |
C8—C7—C6 | 122.47 (17) | C23—C24—H24 | 119.6 |
C8—C7—C2 | 118.64 (18) | C24—C25—C26 | 118.77 (16) |
C6—C7—C2 | 118.89 (18) | C24—C25—C28 | 120.34 (16) |
C9—C8—C7 | 121.66 (18) | C26—C25—C28 | 120.87 (17) |
C9—C8—H8 | 119.2 | C27—C26—C25 | 120.30 (17) |
C7—C8—H8 | 119.2 | C27—C26—H26 | 119.9 |
C8—C9—C10 | 119.44 (19) | C25—C26—H26 | 119.9 |
C8—C9—H9 | 120.3 | C22—C27—C26 | 121.12 (17) |
C10—C9—H9 | 120.3 | C22—C27—H27 | 119.4 |
C1—C10—O2 | 114.29 (16) | C26—C27—H27 | 119.4 |
C1—C10—C9 | 122.25 (18) | N1—C28—C25 | 178.8 (2) |
O2—C10—C9 | 123.46 (17) | O1—C29—C30 | 111.64 (14) |
C12—C11—C20 | 118.51 (17) | O1—C29—H29A | 109.3 |
C12—C11—C1 | 121.18 (17) | C30—C29—H29A | 109.3 |
C20—C11—C1 | 120.18 (17) | O1—C29—H29B | 109.3 |
C11—C12—O1 | 115.20 (16) | C30—C29—H29B | 109.3 |
C11—C12—C13 | 121.56 (17) | H29A—C29—H29B | 108.0 |
O1—C12—C13 | 123.23 (16) | C35—C30—C31 | 118.23 (18) |
C14—C13—C12 | 120.16 (18) | C35—C30—C29 | 121.50 (17) |
C14—C13—H13 | 119.9 | C31—C30—C29 | 120.24 (16) |
C12—C13—H13 | 119.9 | C30—C31—C32 | 120.57 (17) |
C13—C14—C15 | 121.11 (18) | C30—C31—H31 | 119.7 |
C13—C14—H14 | 119.4 | C32—C31—H31 | 119.7 |
C15—C14—H14 | 119.4 | C33—C32—C31 | 120.76 (18) |
C14—C15—C20 | 118.51 (17) | C33—C32—H32 | 119.6 |
C14—C15—C16 | 122.26 (18) | C31—C32—H32 | 119.6 |
C20—C15—C16 | 119.23 (18) | C32—C33—C34 | 118.87 (18) |
C17—C16—C15 | 121.02 (18) | C32—C33—C36 | 121.13 (17) |
C17—C16—H16 | 119.5 | C34—C33—C36 | 119.99 (17) |
C15—C16—H16 | 119.5 | C33—C34—C35 | 119.96 (18) |
C16—C17—C18 | 120.58 (18) | C33—C34—H34 | 120.0 |
C16—C17—H17 | 119.7 | C35—C34—H34 | 120.0 |
C18—C17—H17 | 119.7 | C30—C35—C34 | 121.60 (18) |
C19—C18—C17 | 120.86 (18) | C30—C35—H35 | 119.2 |
C19—C18—H18 | 119.6 | C34—C35—H35 | 119.2 |
C17—C18—H18 | 119.6 | N2—C36—C33 | 178.20 (19) |
C18—C19—C20 | 120.55 (18) | C12—O1—C29 | 117.85 (13) |
C18—C19—H19 | 119.7 | C21—O2—C10 | 124.00 (15) |
Experimental details
Crystal data | |
Chemical formula | C36H24N2O2 |
Mr | 516.57 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 291 |
a, b, c (Å) | 7.835 (1), 10.112 (1), 17.864 (2) |
α, β, γ (°) | 104.696 (2), 91.999 (2), 98.995 (3) |
V (Å3) | 1348.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.26 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.97, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12114, 5312, 4098 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.112, 1.07 |
No. of reflections | 5312 |
No. of parameters | 361 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.16 |
Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.
Because of their highly stable chiral configuration, the 2,2-substituted 1,1-binaphthyls have been extensively used to control many asymmetric processes and have demonstrated outstanding chiral discrimination properties (Pu, 1998). Most 1,1-binaphthyl molecules are C2 symmetric with two identical naphthyl units. The rigid structure and the C2 symmetry of the chiral binaphthyl molecules play an important role in chiral induction (Minatti & Dötz, 2005; Hiroshi, et al., 2005). Herein we report the 1,1'-binaphthyl derivative shown below (I) and its crystal structure.
The crystal data show that in the title compound, C36H24N2O2, the two naphthyl rings are approximately perpendicular to each other and the dihedral angle is 86.68 (3)°. Nevertheless, the two 4-cyanobenzyloxy rings are almost parallel with respect to each other with a dihedral angle of 10.33 (8)°. In Fig. 2, Cg1 and Cg2 are the centroids of ring A (C30—C35) and ring B (C22—C27), respectively. The centroid distance for Cg1—Cg2ii is 3.835 (3) Å, indicating quite strong π-π interactions between the neighbouring molecules. The face to face π-π interactions between the phenyl rings of neighbouring molecules play a very important function in stabilizing the crystal structure. The one-dimensional chain structure is formed by stacking of molecules showing the same absolute configuration via π-π interactions along the a axis. (symmetry code: (i) 1 + x,y,z; (ii) -1 + x,y,z)