

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808009793/zl2104sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808009793/zl2104Isup2.hkl |
CCDC reference: 690885
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.069
- wR factor = 0.170
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 40 Perc. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 3000 Deg. PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C18 .. 5.16 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C33 - C37 .. 5.36 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C30 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C19 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C33 - C37 ... 1.45 Ang. PLAT410_ALERT_2_C Short Intra H...H Contact H1B .. H4 .. 1.99 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
1,1'-Methylenedinaphthalen-2-ol (0.3 g, 1 mmol) and 3-(bromomethyl)benzonitrile (0.392 g, 2 mmol) were dissolved in acetone in the presence of K2CO3 (0.138 g, 1 mmol) and heated under reflux for 3 days. After the mixture was cooled to room temperature, the solution was filtered and the solvents removed in vacuum to afford a white precipitate of the title compound. Colourless crystals suitable for X-ray diffraction were obtained from a solution of 100 mg in 15 ml diethylether by slow evaporation after 3 days.
Positional parameters of all the H atoms were calculated geometrically and the H atoms were set to ride on the C and N atoms to which they are bonded, with Uiso(H) = 1.2Ueq(C or N).
Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008); program(s) used to refine structure: SHELXTL/PC (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).
![]() | Fig. 1. A view of the compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. |
C37H26N2O2 | Z = 2 |
Mr = 530.60 | F(000) = 556.0 |
Triclinic, P1 | Dx = 1.252 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3123 (19) Å | Cell parameters from 7383 reflections |
b = 12.130 (2) Å | θ = 3.2–27.5° |
c = 12.682 (3) Å | µ = 0.08 mm−1 |
α = 79.71 (3)° | T = 293 K |
β = 86.58 (3)° | Block, colourless |
γ = 87.10 (3)° | 0.40 × 0.20 × 0.20 mm |
V = 1405.9 (5) Å3 |
Rigaku Mercury2 diffractometer | 5505 independent reflections |
Radiation source: fine-focus sealed tube | 2197 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.074 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 26.0°, θmin = 3.2° |
CCD_Profile_fitting scans | h = −11→11 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −14→14 |
Tmin = 0.929, Tmax = 0.976 | l = −15→15 |
13073 measured reflections |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0621P)2] where P = (Fo2 + 2Fc2)/3 |
5505 reflections | (Δ/σ)max = 0.001 |
370 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C37H26N2O2 | γ = 87.10 (3)° |
Mr = 530.60 | V = 1405.9 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3123 (19) Å | Mo Kα radiation |
b = 12.130 (2) Å | µ = 0.08 mm−1 |
c = 12.682 (3) Å | T = 293 K |
α = 79.71 (3)° | 0.40 × 0.20 × 0.20 mm |
β = 86.58 (3)° |
Rigaku Mercury2 diffractometer | 5505 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 2197 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.976 | Rint = 0.074 |
13073 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 0.92 | Δρmax = 0.18 e Å−3 |
5505 reflections | Δρmin = −0.18 e Å−3 |
370 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 | ||
C1 | 0.3027 (3) | 0.9398 (2) | 0.0249 (2) | 0.0608 (9) | |
H1A | 0.2769 | 1.0188 | 0.0042 | 0.073* | |
H1B | 0.3652 | 0.9178 | −0.0325 | 0.073* | |
C2 | 0.1670 (3) | 0.8741 (2) | 0.0352 (2) | 0.0523 (8) | |
C3 | 0.1464 (4) | 0.7897 (3) | −0.0270 (2) | 0.0607 (9) | |
C4 | 0.2492 (4) | 0.7613 (3) | −0.1054 (3) | 0.0763 (10) | |
H4 | 0.3356 | 0.7980 | −0.1171 | 0.092* | |
C5 | 0.2242 (6) | 0.6817 (4) | −0.1637 (3) | 0.1065 (14) | |
H5 | 0.2935 | 0.6650 | −0.2151 | 0.128* | |
C6 | 0.0968 (7) | 0.6243 (4) | −0.1482 (4) | 0.1182 (17) | |
H6 | 0.0820 | 0.5695 | −0.1887 | 0.142* | |
C7 | −0.0061 (5) | 0.6482 (3) | −0.0739 (3) | 0.0988 (13) | |
H7 | −0.0906 | 0.6091 | −0.0637 | 0.119* | |
C8 | 0.0143 (4) | 0.7320 (3) | −0.0121 (3) | 0.0692 (9) | |
C9 | −0.0890 (4) | 0.7570 (3) | 0.0656 (3) | 0.0763 (10) | |
H9 | −0.1728 | 0.7170 | 0.0774 | 0.092* | |
C10 | −0.0707 (3) | 0.8378 (3) | 0.1242 (2) | 0.0689 (9) | |
H10 | −0.1411 | 0.8540 | 0.1750 | 0.083* | |
C11 | 0.0578 (3) | 0.8971 (3) | 0.1065 (2) | 0.0537 (8) | |
C12 | −0.0149 (3) | 1.0114 (3) | 0.2408 (2) | 0.0720 (10) | |
H12A | −0.1122 | 1.0119 | 0.2173 | 0.086* | |
H12B | 0.0025 | 1.0864 | 0.2523 | 0.086* | |
C13 | −0.0040 (3) | 0.9310 (2) | 0.3465 (2) | 0.0552 (8) | |
C14 | 0.1197 (3) | 0.8661 (2) | 0.3723 (2) | 0.0545 (8) | |
H14 | 0.1972 | 0.8681 | 0.3224 | 0.065* | |
C15 | 0.1290 (4) | 0.7982 (2) | 0.4718 (2) | 0.0585 (8) | |
C16 | 0.0151 (4) | 0.7942 (3) | 0.5460 (3) | 0.0792 (11) | |
H16 | 0.0210 | 0.7474 | 0.6124 | 0.095* | |
C17 | −0.1075 (4) | 0.8592 (4) | 0.5223 (3) | 0.0910 (12) | |
H17 | −0.1842 | 0.8577 | 0.5729 | 0.109* | |
C18 | −0.1164 (3) | 0.9276 (3) | 0.4220 (3) | 0.0742 (10) | |
H18 | −0.1996 | 0.9715 | 0.4060 | 0.089* | |
C19 | 0.2585 (5) | 0.7344 (3) | 0.5006 (3) | 0.0772 (10) | |
C20 | 0.3869 (3) | 0.9240 (2) | 0.1264 (2) | 0.0533 (8) | |
C21 | 0.4046 (3) | 1.0118 (3) | 0.1852 (2) | 0.0561 (8) | |
C22 | 0.3464 (3) | 1.1227 (3) | 0.1556 (3) | 0.0714 (9) | |
H22 | 0.2943 | 1.1404 | 0.0940 | 0.086* | |
C23 | 0.3649 (4) | 1.2042 (3) | 0.2149 (3) | 0.0846 (11) | |
H23 | 0.3250 | 1.2760 | 0.1935 | 0.102* | |
C24 | 0.4431 (4) | 1.1805 (3) | 0.3075 (3) | 0.0841 (11) | |
H24 | 0.4561 | 1.2365 | 0.3470 | 0.101* | |
C25 | 0.4999 (3) | 1.0755 (3) | 0.3396 (3) | 0.0777 (10) | |
H25 | 0.5511 | 1.0600 | 0.4017 | 0.093* | |
C26 | 0.4827 (3) | 0.9889 (3) | 0.2803 (3) | 0.0624 (9) | |
C27 | 0.5416 (4) | 0.8801 (3) | 0.3132 (3) | 0.0774 (10) | |
H27 | 0.5917 | 0.8647 | 0.3758 | 0.093* | |
C28 | 0.5275 (3) | 0.7970 (3) | 0.2567 (3) | 0.0739 (10) | |
H28 | 0.5684 | 0.7259 | 0.2797 | 0.089* | |
C29 | 0.4503 (3) | 0.8193 (3) | 0.1627 (3) | 0.0596 (8) | |
C30 | 0.4664 (4) | 0.6241 (3) | 0.1401 (3) | 0.0855 (11) | |
H30A | 0.5641 | 0.6153 | 0.1636 | 0.103* | |
H30B | 0.4609 | 0.5814 | 0.0828 | 0.103* | |
C31 | 0.3651 (4) | 0.5757 (3) | 0.2329 (3) | 0.0658 (9) | |
C32 | 0.2190 (4) | 0.6039 (3) | 0.2314 (2) | 0.0680 (9) | |
H32 | 0.1828 | 0.6548 | 0.1745 | 0.082* | |
C33 | 0.1263 (4) | 0.5558 (3) | 0.3156 (3) | 0.0626 (8) | |
C34 | 0.1783 (4) | 0.4822 (3) | 0.4006 (3) | 0.0774 (10) | |
H34 | 0.1158 | 0.4516 | 0.4570 | 0.093* | |
C35 | 0.3224 (5) | 0.4532 (3) | 0.4027 (3) | 0.0867 (12) | |
H35 | 0.3577 | 0.4018 | 0.4597 | 0.104* | |
C36 | 0.4153 (4) | 0.5011 (3) | 0.3195 (3) | 0.0812 (11) | |
H36 | 0.5133 | 0.4826 | 0.3221 | 0.097* | |
C37 | −0.0261 (5) | 0.5865 (3) | 0.3164 (3) | 0.0762 (10) | |
N1 | −0.1484 (4) | 0.6073 (3) | 0.3198 (3) | 0.1080 (12) | |
N2 | 0.3622 (4) | 0.6844 (3) | 0.5255 (3) | 0.1119 (12) | |
O1 | 0.0827 (2) | 0.98473 (17) | 0.15795 (15) | 0.0632 (6) | |
O2 | 0.4363 (2) | 0.74029 (18) | 0.09827 (17) | 0.0715 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.063 (2) | 0.063 (2) | 0.0519 (19) | −0.0079 (17) | 0.0066 (17) | 0.0001 (15) |
C2 | 0.058 (2) | 0.061 (2) | 0.0338 (16) | −0.0052 (16) | −0.0026 (15) | 0.0048 (14) |
C3 | 0.077 (2) | 0.060 (2) | 0.0403 (18) | 0.0011 (19) | −0.0095 (18) | 0.0054 (16) |
C4 | 0.102 (3) | 0.074 (2) | 0.054 (2) | −0.001 (2) | −0.005 (2) | −0.0130 (19) |
C5 | 0.140 (4) | 0.106 (4) | 0.078 (3) | 0.009 (3) | −0.009 (3) | −0.030 (3) |
C6 | 0.169 (5) | 0.089 (3) | 0.103 (4) | −0.009 (4) | −0.040 (4) | −0.024 (3) |
C7 | 0.113 (4) | 0.096 (3) | 0.088 (3) | −0.026 (3) | −0.031 (3) | −0.005 (3) |
C8 | 0.083 (3) | 0.069 (2) | 0.053 (2) | −0.011 (2) | −0.023 (2) | 0.0061 (18) |
C9 | 0.069 (2) | 0.088 (3) | 0.065 (2) | −0.018 (2) | −0.020 (2) | 0.016 (2) |
C10 | 0.055 (2) | 0.093 (3) | 0.051 (2) | −0.002 (2) | −0.0088 (17) | 0.0085 (19) |
C11 | 0.058 (2) | 0.061 (2) | 0.0388 (17) | 0.0039 (17) | −0.0137 (16) | 0.0025 (15) |
C12 | 0.063 (2) | 0.091 (3) | 0.060 (2) | 0.0176 (19) | −0.0102 (19) | −0.0102 (19) |
C13 | 0.0423 (18) | 0.075 (2) | 0.0481 (18) | 0.0035 (16) | −0.0009 (15) | −0.0132 (16) |
C14 | 0.0498 (19) | 0.066 (2) | 0.0461 (18) | 0.0036 (16) | −0.0017 (15) | −0.0074 (15) |
C15 | 0.062 (2) | 0.062 (2) | 0.0524 (19) | −0.0055 (17) | −0.0116 (18) | −0.0072 (17) |
C16 | 0.093 (3) | 0.089 (3) | 0.053 (2) | −0.024 (2) | −0.004 (2) | −0.0009 (19) |
C17 | 0.068 (3) | 0.133 (4) | 0.072 (3) | −0.023 (3) | 0.017 (2) | −0.020 (2) |
C18 | 0.047 (2) | 0.104 (3) | 0.075 (2) | −0.0034 (19) | −0.0025 (19) | −0.024 (2) |
C19 | 0.096 (3) | 0.071 (2) | 0.064 (2) | 0.008 (2) | −0.024 (2) | −0.0060 (18) |
C20 | 0.0409 (18) | 0.059 (2) | 0.0536 (19) | −0.0040 (16) | 0.0058 (15) | 0.0047 (16) |
C21 | 0.0402 (18) | 0.065 (2) | 0.060 (2) | −0.0108 (16) | 0.0035 (16) | −0.0036 (17) |
C22 | 0.062 (2) | 0.075 (2) | 0.074 (2) | −0.0013 (19) | −0.0087 (19) | −0.003 (2) |
C23 | 0.081 (3) | 0.075 (3) | 0.100 (3) | 0.000 (2) | −0.007 (2) | −0.022 (2) |
C24 | 0.064 (3) | 0.102 (3) | 0.094 (3) | −0.009 (2) | −0.001 (2) | −0.038 (2) |
C25 | 0.051 (2) | 0.103 (3) | 0.084 (3) | −0.015 (2) | −0.0081 (19) | −0.025 (2) |
C26 | 0.0375 (18) | 0.075 (2) | 0.073 (2) | −0.0094 (17) | −0.0015 (17) | −0.0056 (19) |
C27 | 0.056 (2) | 0.092 (3) | 0.083 (3) | −0.013 (2) | −0.0246 (19) | −0.002 (2) |
C28 | 0.048 (2) | 0.073 (2) | 0.097 (3) | −0.0018 (18) | −0.021 (2) | 0.002 (2) |
C29 | 0.0405 (18) | 0.066 (2) | 0.071 (2) | −0.0077 (17) | 0.0068 (17) | −0.0100 (19) |
C30 | 0.077 (3) | 0.070 (3) | 0.105 (3) | 0.011 (2) | 0.007 (2) | −0.011 (2) |
C31 | 0.068 (2) | 0.056 (2) | 0.070 (2) | 0.0080 (18) | 0.0004 (19) | −0.0091 (17) |
C32 | 0.077 (3) | 0.067 (2) | 0.054 (2) | 0.0040 (19) | −0.0086 (19) | 0.0052 (16) |
C33 | 0.072 (2) | 0.057 (2) | 0.058 (2) | 0.0037 (18) | −0.0107 (19) | −0.0052 (17) |
C34 | 0.101 (3) | 0.066 (2) | 0.059 (2) | 0.011 (2) | 0.002 (2) | −0.0009 (18) |
C35 | 0.122 (4) | 0.065 (2) | 0.066 (3) | 0.021 (2) | −0.007 (3) | 0.0030 (19) |
C36 | 0.089 (3) | 0.060 (2) | 0.091 (3) | 0.027 (2) | −0.024 (2) | −0.007 (2) |
C37 | 0.087 (3) | 0.084 (3) | 0.051 (2) | −0.002 (2) | −0.002 (2) | 0.0059 (17) |
N1 | 0.078 (2) | 0.142 (3) | 0.088 (2) | 0.003 (2) | 0.005 (2) | 0.018 (2) |
N2 | 0.131 (3) | 0.099 (3) | 0.106 (3) | 0.038 (2) | −0.054 (2) | −0.015 (2) |
O1 | 0.0631 (14) | 0.0748 (15) | 0.0488 (12) | 0.0082 (12) | −0.0002 (11) | −0.0070 (11) |
O2 | 0.0707 (15) | 0.0648 (15) | 0.0739 (15) | 0.0050 (12) | 0.0047 (12) | −0.0038 (12) |
C1—C2 | 1.515 (4) | C18—H18 | 0.9300 |
C1—C20 | 1.525 (4) | C19—N2 | 1.144 (4) |
C1—H1A | 0.9700 | C20—C29 | 1.386 (4) |
C1—H1B | 0.9700 | C20—C21 | 1.427 (4) |
C2—C11 | 1.372 (4) | C21—C22 | 1.419 (4) |
C2—C3 | 1.425 (4) | C21—C26 | 1.423 (4) |
C3—C4 | 1.414 (4) | C22—C23 | 1.369 (4) |
C3—C8 | 1.432 (4) | C22—H22 | 0.9300 |
C4—C5 | 1.354 (5) | C23—C24 | 1.397 (5) |
C4—H4 | 0.9300 | C23—H23 | 0.9300 |
C5—C6 | 1.392 (6) | C24—C25 | 1.357 (4) |
C5—H5 | 0.9300 | C24—H24 | 0.9300 |
C6—C7 | 1.360 (5) | C25—C26 | 1.417 (4) |
C6—H6 | 0.9300 | C25—H25 | 0.9300 |
C7—C8 | 1.417 (5) | C26—C27 | 1.405 (4) |
C7—H7 | 0.9300 | C27—C28 | 1.352 (4) |
C8—C9 | 1.397 (4) | C27—H27 | 0.9300 |
C9—C10 | 1.355 (4) | C28—C29 | 1.407 (4) |
C9—H9 | 0.9300 | C28—H28 | 0.9300 |
C10—C11 | 1.413 (4) | C29—O2 | 1.381 (3) |
C10—H10 | 0.9300 | C30—O2 | 1.434 (3) |
C11—O1 | 1.379 (3) | C30—C31 | 1.515 (4) |
C12—O1 | 1.418 (3) | C30—H30A | 0.9700 |
C12—C13 | 1.516 (4) | C30—H30B | 0.9700 |
C12—H12A | 0.9700 | C31—C36 | 1.382 (4) |
C12—H12B | 0.9700 | C31—C32 | 1.387 (4) |
C13—C18 | 1.373 (4) | C32—C33 | 1.394 (4) |
C13—C14 | 1.384 (4) | C32—H32 | 0.9300 |
C14—C15 | 1.382 (4) | C33—C34 | 1.367 (4) |
C14—H14 | 0.9300 | C33—C37 | 1.449 (5) |
C15—C16 | 1.373 (4) | C34—C35 | 1.370 (5) |
C15—C19 | 1.429 (5) | C34—H34 | 0.9300 |
C16—C17 | 1.371 (5) | C35—C36 | 1.386 (4) |
C16—H16 | 0.9300 | C35—H35 | 0.9300 |
C17—C18 | 1.394 (4) | C36—H36 | 0.9300 |
C17—H17 | 0.9300 | C37—N1 | 1.154 (4) |
C2—C1—C20 | 114.8 (2) | C17—C18—H18 | 119.5 |
C2—C1—H1A | 108.6 | N2—C19—C15 | 178.6 (4) |
C20—C1—H1A | 108.6 | C29—C20—C21 | 118.5 (3) |
C2—C1—H1B | 108.6 | C29—C20—C1 | 118.3 (3) |
C20—C1—H1B | 108.6 | C21—C20—C1 | 123.2 (3) |
H1A—C1—H1B | 107.6 | C22—C21—C26 | 116.8 (3) |
C11—C2—C3 | 118.1 (3) | C22—C21—C20 | 123.8 (3) |
C11—C2—C1 | 119.0 (3) | C26—C21—C20 | 119.4 (3) |
C3—C2—C1 | 122.9 (3) | C23—C22—C21 | 121.8 (3) |
C4—C3—C2 | 123.2 (3) | C23—C22—H22 | 119.1 |
C4—C3—C8 | 117.7 (3) | C21—C22—H22 | 119.1 |
C2—C3—C8 | 119.1 (3) | C22—C23—C24 | 120.6 (4) |
C5—C4—C3 | 121.2 (4) | C22—C23—H23 | 119.7 |
C5—C4—H4 | 119.4 | C24—C23—H23 | 119.7 |
C3—C4—H4 | 119.4 | C25—C24—C23 | 119.8 (4) |
C4—C5—C6 | 121.2 (4) | C25—C24—H24 | 120.1 |
C4—C5—H5 | 119.4 | C23—C24—H24 | 120.1 |
C6—C5—H5 | 119.4 | C24—C25—C26 | 121.2 (3) |
C7—C6—C5 | 120.3 (4) | C24—C25—H25 | 119.4 |
C7—C6—H6 | 119.9 | C26—C25—H25 | 119.4 |
C5—C6—H6 | 119.9 | C27—C26—C25 | 121.4 (3) |
C6—C7—C8 | 120.6 (4) | C27—C26—C21 | 118.9 (3) |
C6—C7—H7 | 119.7 | C25—C26—C21 | 119.8 (3) |
C8—C7—H7 | 119.7 | C28—C27—C26 | 122.0 (3) |
C9—C8—C7 | 121.6 (4) | C28—C27—H27 | 119.0 |
C9—C8—C3 | 119.2 (3) | C26—C27—H27 | 119.0 |
C7—C8—C3 | 119.1 (4) | C27—C28—C29 | 119.3 (3) |
C10—C9—C8 | 121.9 (4) | C27—C28—H28 | 120.3 |
C10—C9—H9 | 119.1 | C29—C28—H28 | 120.3 |
C8—C9—H9 | 119.1 | O2—C29—C20 | 115.3 (3) |
C9—C10—C11 | 118.5 (3) | O2—C29—C28 | 122.8 (3) |
C9—C10—H10 | 120.7 | C20—C29—C28 | 121.9 (3) |
C11—C10—H10 | 120.7 | O2—C30—C31 | 114.0 (3) |
C2—C11—O1 | 114.2 (3) | O2—C30—H30A | 108.7 |
C2—C11—C10 | 123.0 (3) | C31—C30—H30A | 108.7 |
O1—C11—C10 | 122.7 (3) | O2—C30—H30B | 108.7 |
O1—C12—C13 | 114.0 (2) | C31—C30—H30B | 108.7 |
O1—C12—H12A | 108.7 | H30A—C30—H30B | 107.6 |
C13—C12—H12A | 108.7 | C36—C31—C32 | 118.5 (3) |
O1—C12—H12B | 108.7 | C36—C31—C30 | 121.1 (3) |
C13—C12—H12B | 108.7 | C32—C31—C30 | 120.4 (3) |
H12A—C12—H12B | 107.6 | C31—C32—C33 | 119.8 (3) |
C18—C13—C14 | 118.7 (3) | C31—C32—H32 | 120.1 |
C18—C13—C12 | 119.2 (3) | C33—C32—H32 | 120.1 |
C14—C13—C12 | 122.0 (3) | C34—C33—C32 | 120.7 (3) |
C15—C14—C13 | 120.6 (3) | C34—C33—C37 | 118.9 (3) |
C15—C14—H14 | 119.7 | C32—C33—C37 | 120.4 (3) |
C13—C14—H14 | 119.7 | C33—C34—C35 | 120.1 (3) |
C16—C15—C14 | 120.2 (3) | C33—C34—H34 | 120.0 |
C16—C15—C19 | 118.9 (3) | C35—C34—H34 | 120.0 |
C14—C15—C19 | 120.9 (3) | C34—C35—C36 | 119.6 (3) |
C17—C16—C15 | 120.0 (3) | C34—C35—H35 | 120.2 |
C17—C16—H16 | 120.0 | C36—C35—H35 | 120.2 |
C15—C16—H16 | 120.0 | C31—C36—C35 | 121.3 (3) |
C16—C17—C18 | 119.6 (3) | C31—C36—H36 | 119.3 |
C16—C17—H17 | 120.2 | C35—C36—H36 | 119.3 |
C18—C17—H17 | 120.2 | N1—C37—C33 | 177.5 (4) |
C13—C18—C17 | 121.0 (3) | C11—O1—C12 | 120.4 (3) |
C13—C18—H18 | 119.5 | C29—O2—C30 | 119.5 (3) |
C20—C1—C2—C11 | 62.9 (3) | C1—C20—C21—C22 | −0.2 (4) |
C20—C1—C2—C3 | −117.8 (3) | C29—C20—C21—C26 | −1.7 (4) |
C11—C2—C3—C4 | 177.9 (3) | C1—C20—C21—C26 | 178.9 (2) |
C1—C2—C3—C4 | −1.4 (4) | C26—C21—C22—C23 | 0.3 (5) |
C11—C2—C3—C8 | −0.5 (4) | C20—C21—C22—C23 | 179.4 (3) |
C1—C2—C3—C8 | −179.8 (3) | C21—C22—C23—C24 | 0.3 (5) |
C2—C3—C4—C5 | −179.0 (3) | C22—C23—C24—C25 | −0.7 (5) |
C8—C3—C4—C5 | −0.6 (5) | C23—C24—C25—C26 | 0.6 (5) |
C3—C4—C5—C6 | −0.4 (6) | C24—C25—C26—C27 | 179.9 (3) |
C4—C5—C6—C7 | 0.5 (7) | C24—C25—C26—C21 | 0.0 (5) |
C5—C6—C7—C8 | 0.5 (7) | C22—C21—C26—C27 | 179.6 (3) |
C6—C7—C8—C9 | −179.2 (4) | C20—C21—C26—C27 | 0.5 (4) |
C6—C7—C8—C3 | −1.5 (5) | C22—C21—C26—C25 | −0.4 (4) |
C4—C3—C8—C9 | 179.3 (3) | C20—C21—C26—C25 | −179.6 (3) |
C2—C3—C8—C9 | −2.3 (4) | C25—C26—C27—C28 | −179.2 (3) |
C4—C3—C8—C7 | 1.5 (4) | C21—C26—C27—C28 | 0.7 (5) |
C2—C3—C8—C7 | 180.0 (3) | C26—C27—C28—C29 | −0.7 (5) |
C7—C8—C9—C10 | −179.4 (3) | C21—C20—C29—O2 | −176.2 (2) |
C3—C8—C9—C10 | 2.9 (5) | C1—C20—C29—O2 | 3.3 (4) |
C8—C9—C10—C11 | −0.8 (5) | C21—C20—C29—C28 | 1.7 (4) |
C3—C2—C11—O1 | −175.9 (2) | C1—C20—C29—C28 | −178.8 (3) |
C1—C2—C11—O1 | 3.5 (3) | C27—C28—C29—O2 | 177.3 (3) |
C3—C2—C11—C10 | 2.8 (4) | C27—C28—C29—C20 | −0.5 (5) |
C1—C2—C11—C10 | −177.9 (3) | O2—C30—C31—C36 | −140.6 (3) |
C9—C10—C11—C2 | −2.2 (4) | O2—C30—C31—C32 | 40.7 (4) |
C9—C10—C11—O1 | 176.4 (3) | C36—C31—C32—C33 | −0.9 (5) |
O1—C12—C13—C18 | −161.5 (3) | C30—C31—C32—C33 | 177.8 (3) |
O1—C12—C13—C14 | 23.0 (4) | C31—C32—C33—C34 | 0.9 (5) |
C18—C13—C14—C15 | 0.8 (4) | C31—C32—C33—C37 | 178.6 (3) |
C12—C13—C14—C15 | 176.4 (3) | C32—C33—C34—C35 | −1.2 (5) |
C13—C14—C15—C16 | 0.2 (5) | C37—C33—C34—C35 | −178.9 (3) |
C13—C14—C15—C19 | −177.4 (3) | C33—C34—C35—C36 | 1.5 (5) |
C14—C15—C16—C17 | −1.1 (5) | C32—C31—C36—C35 | 1.2 (5) |
C19—C15—C16—C17 | 176.5 (3) | C30—C31—C36—C35 | −177.5 (3) |
C15—C16—C17—C18 | 1.1 (5) | C34—C35—C36—C31 | −1.5 (5) |
C14—C13—C18—C17 | −0.8 (5) | C2—C11—O1—C12 | −174.4 (2) |
C12—C13—C18—C17 | −176.6 (3) | C10—C11—O1—C12 | 7.0 (4) |
C16—C17—C18—C13 | −0.1 (5) | C13—C12—O1—C11 | 75.5 (3) |
C2—C1—C20—C29 | 66.3 (3) | C20—C29—O2—C30 | −165.0 (2) |
C2—C1—C20—C21 | −114.2 (3) | C28—C29—O2—C30 | 17.0 (4) |
C29—C20—C21—C22 | 179.2 (3) | C31—C30—O2—C29 | 64.3 (4) |
Experimental details
Crystal data | |
Chemical formula | C37H26N2O2 |
Mr | 530.60 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.3123 (19), 12.130 (2), 12.682 (3) |
α, β, γ (°) | 79.71 (3), 86.58 (3), 87.10 (3) |
V (Å3) | 1405.9 (5) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Rigaku Mercury2 diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.929, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13073, 5505, 2197 |
Rint | 0.074 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.170, 0.92 |
No. of reflections | 5505 |
No. of parameters | 370 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.18 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXTL/PC (Sheldrick, 2008).
Nitrile derivatives are important materials in the synthesis of some heterocyclic molecules (Radl et al., 2000). Recently, we have reported a few benzonitrile compounds (Fu & Zhao, 2007). As an extension of our work on the structural characterization of nitrile compounds the structure of the title compound is reported here.
As shown in Fig. 1, the two naphthyl rings in the title compound are bridged by one C atom (C1) and are approximately perpendicular to each other with an dihedral angle of 83.3 (9)°. The two 3-cyanobenzyloxy rings, on the other hand are almost parallel to each other with a dihedral angle of 15.53 (0.23) °.