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In the title compound, C36H24N2O2, the two naphthyl systems are approximately perpendicular to each other and the two 4-cyano­benz­yloxy rings are almost parallel to each other. There are strong π–π inter­actions [3.835 (3) Å] between neighbouring mol­ecules. The face-to-face π–π inter­actions between the benzene rings of neighbouring mol­ecules stabilize the crystal structure to form a one-dimensional chain structure along the a axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027596/im2019sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027596/im2019Isup2.hkl
Contains datablock I

CCDC reference: 654950

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.053
  • wR factor = 0.112
  • Data-to-parameter ratio = 14.7

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Comment top

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)

Related literature top

For related literature, see: Hiroshi et al. (2005); Minatti & Dötz (2005); Pu (1998).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The molecular structure of the R-enantiomer of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of the 1-D chain structure along a axis. (symmetry code: (i) 1 + x,y,z; (ii) -1 + x,y,z)
4,4'-[1,1'-Binaphthalene-2,2'-diyldi(oxymethylene)]benzonitrile top
Crystal data top
C36H24N2O2Z = 2
Mr = 516.57F(000) = 540
Triclinic, P1Dx = 1.273 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.835 (1) ÅCell parameters from 3754 reflections
b = 10.112 (1) Åθ = 2.1–22.0°
c = 17.864 (2) ŵ = 0.08 mm1
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
Data collection top
Bruker SMART APEX CCD
diffractometer
5312 independent reflections
Radiation source: sealed tube4098 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 26.0°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 99
Tmin = 0.97, Tmax = 0.98k = 1212
12114 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-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 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C36H24N2O2γ = 98.995 (3)°
Mr = 516.57V = 1348.0 (3) Å3
Triclinic, P1Z = 2
a = 7.835 (1) ÅMo Kα radiation
b = 10.112 (1) ŵ = 0.08 mm1
c = 17.864 (2) ÅT = 291 K
α = 104.696 (2)°0.30 × 0.26 × 0.24 mm
β = 91.999 (2)°
Data collection top
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 = 0.98Rint = 0.033
12114 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.07Δρmax = 0.13 e Å3
5312 reflectionsΔρmin = 0.16 e Å3
361 parameters
Special details top

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

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2017 (3)0.29019 (19)0.41549 (11)0.0433 (4)
C20.1441 (2)0.30558 (19)0.49104 (11)0.0426 (4)
C30.0597 (2)0.19262 (19)0.51564 (11)0.0411 (4)
H30.03860.10480.48110.049*
C40.0081 (2)0.20905 (19)0.58890 (10)0.0389 (4)
H40.04660.13260.60410.047*
C50.0369 (2)0.33958 (19)0.64112 (11)0.0398 (4)
H50.00300.35000.69140.048*
C60.1142 (2)0.4520 (2)0.61907 (11)0.0451 (4)
H60.13000.53910.65410.054*
C70.1709 (3)0.4387 (2)0.54415 (12)0.0455 (4)
C80.2511 (2)0.5520 (2)0.51978 (12)0.0465 (5)
H80.26710.64010.55400.056*
C90.3061 (3)0.5372 (2)0.44789 (11)0.0467 (5)
H90.35940.61420.43280.056*
C100.2822 (3)0.4056 (2)0.39633 (11)0.0462 (5)
C110.1844 (2)0.15117 (19)0.35772 (10)0.0398 (4)
C120.0469 (2)0.10386 (19)0.30272 (10)0.0399 (4)
C130.0371 (2)0.01979 (19)0.24483 (11)0.0432 (4)
H130.05790.04990.20840.052*
C140.1651 (2)0.0958 (2)0.24160 (11)0.0432 (4)
H140.15860.17680.20200.052*
C150.3073 (2)0.0546 (2)0.29676 (11)0.0441 (4)
C160.4430 (2)0.1339 (2)0.29537 (11)0.0442 (4)
H160.43980.21430.25570.053*
C170.5746 (2)0.0945 (2)0.35025 (11)0.0434 (4)
H170.66090.14850.34870.052*
C180.5836 (2)0.0262 (2)0.40949 (11)0.0425 (4)
H180.67510.05150.44770.051*
C190.4591 (2)0.1089 (2)0.41237 (11)0.0437 (4)
H190.46890.19080.45160.052*
C200.3159 (2)0.0704 (2)0.35593 (11)0.0430 (4)
C210.4282 (2)0.47657 (19)0.29425 (11)0.0413 (4)
H21A0.53790.51300.32500.050*
H21B0.36540.55270.29640.050*
C220.4599 (3)0.4117 (2)0.21174 (11)0.0450 (4)
C230.5443 (2)0.4935 (2)0.16926 (11)0.0448 (4)
H230.58690.58660.19250.054*
C240.5663 (2)0.43691 (19)0.09120 (10)0.0387 (4)
H240.62320.49300.06260.046*
C250.5052 (2)0.29965 (18)0.05614 (10)0.0373 (4)
C260.4246 (2)0.2174 (2)0.09994 (11)0.0420 (4)
H260.38550.12350.07740.050*
C270.4018 (2)0.27383 (19)0.17680 (10)0.0408 (4)
H270.34610.21750.20550.049*
C280.5283 (2)0.24323 (19)0.02306 (10)0.0374 (4)
C290.2123 (2)0.15527 (18)0.24646 (10)0.0373 (4)
H29A0.30470.20700.26300.045*
H29B0.26070.05720.23390.045*
C300.1420 (2)0.19107 (19)0.17444 (10)0.0392 (4)
C310.0440 (2)0.3190 (2)0.18004 (11)0.0426 (4)
H310.01780.38260.22830.051*
C320.0161 (2)0.3539 (2)0.11436 (11)0.0448 (4)
H320.08310.44040.11910.054*
C330.0220 (2)0.26212 (19)0.04243 (11)0.0407 (4)
C340.1196 (2)0.1337 (2)0.03658 (12)0.0451 (5)
H340.14620.07010.01170.054*
C350.1781 (2)0.0996 (2)0.10237 (11)0.0442 (4)
H350.24350.01240.09770.053*
C360.0382 (2)0.29689 (18)0.02469 (11)0.0400 (4)
N10.5449 (2)0.19579 (17)0.08698 (9)0.0439 (4)
N20.0847 (2)0.32188 (16)0.08039 (9)0.0445 (4)
O10.07884 (15)0.18709 (13)0.30920 (7)0.0389 (3)
O20.33595 (18)0.38044 (13)0.32265 (7)0.0471 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0440 (10)0.0398 (10)0.0434 (10)0.0031 (8)0.0030 (8)0.0087 (8)
C20.0454 (10)0.0367 (9)0.0446 (11)0.0094 (8)0.0047 (8)0.0073 (8)
C30.0424 (10)0.0422 (10)0.0401 (10)0.0133 (8)0.0141 (8)0.0083 (8)
C40.0397 (9)0.0431 (10)0.0386 (9)0.0126 (8)0.0180 (7)0.0138 (8)
C50.0382 (9)0.0442 (10)0.0398 (10)0.0152 (8)0.0226 (8)0.0088 (8)
C60.0414 (10)0.0412 (10)0.0494 (11)0.0102 (8)0.0146 (8)0.0029 (8)
C70.0477 (11)0.0373 (10)0.0481 (11)0.0087 (8)0.0060 (8)0.0036 (8)
C80.0438 (10)0.0374 (10)0.0520 (12)0.0035 (8)0.0054 (9)0.0020 (8)
C90.0473 (11)0.0384 (10)0.0496 (11)0.0026 (8)0.0036 (9)0.0087 (8)
C100.0486 (11)0.0419 (10)0.0431 (11)0.0035 (8)0.0080 (8)0.0082 (8)
C110.0402 (10)0.0414 (10)0.0389 (10)0.0067 (8)0.0097 (8)0.0115 (8)
C120.0379 (10)0.0437 (10)0.0396 (10)0.0129 (8)0.0048 (8)0.0100 (8)
C130.0430 (10)0.0427 (10)0.0406 (10)0.0121 (8)0.0022 (8)0.0024 (8)
C140.0426 (10)0.0428 (10)0.0431 (10)0.0132 (8)0.0068 (8)0.0053 (8)
C150.0433 (10)0.0484 (11)0.0430 (10)0.0147 (9)0.0115 (8)0.0110 (8)
C160.0417 (10)0.0500 (11)0.0456 (11)0.0190 (9)0.0168 (8)0.0124 (9)
C170.0443 (10)0.0474 (11)0.0416 (10)0.0144 (8)0.0128 (8)0.0122 (8)
C180.0427 (10)0.0466 (11)0.0403 (10)0.0083 (8)0.0019 (8)0.0148 (8)
C190.0388 (10)0.0486 (11)0.0432 (10)0.0040 (8)0.0047 (8)0.0132 (8)
C200.0400 (10)0.0452 (10)0.0445 (10)0.0064 (8)0.0095 (8)0.0128 (8)
C210.0437 (10)0.0380 (10)0.0423 (10)0.0001 (8)0.0125 (8)0.0137 (8)
C220.0477 (11)0.0413 (10)0.0444 (11)0.0014 (8)0.0122 (8)0.0110 (8)
C230.0415 (10)0.0478 (11)0.0435 (10)0.0055 (8)0.0132 (8)0.0092 (8)
C240.0381 (9)0.0427 (10)0.0412 (10)0.0144 (8)0.0169 (7)0.0153 (8)
C250.0403 (9)0.0396 (9)0.0372 (9)0.0169 (8)0.0174 (7)0.0117 (7)
C260.0419 (10)0.0416 (10)0.0409 (10)0.0074 (8)0.0158 (8)0.0061 (8)
C270.0442 (10)0.0375 (9)0.0412 (10)0.0000 (8)0.0173 (8)0.0136 (8)
C280.0417 (10)0.0419 (10)0.0386 (10)0.0210 (8)0.0202 (8)0.0182 (8)
C290.0388 (9)0.0365 (9)0.0387 (9)0.0106 (7)0.0032 (7)0.0119 (7)
C300.0368 (9)0.0406 (10)0.0395 (10)0.0100 (8)0.0065 (7)0.0086 (8)
C310.0394 (10)0.0425 (10)0.0422 (10)0.0056 (8)0.0018 (8)0.0056 (8)
C320.0423 (10)0.0420 (10)0.0444 (11)0.0030 (8)0.0023 (8)0.0074 (8)
C330.0386 (10)0.0398 (10)0.0442 (10)0.0037 (8)0.0014 (8)0.0140 (8)
C340.0411 (10)0.0424 (10)0.0466 (11)0.0018 (8)0.0051 (8)0.0067 (8)
C350.0402 (10)0.0454 (10)0.0413 (10)0.0023 (8)0.0061 (8)0.0078 (8)
C360.0389 (10)0.0361 (9)0.0451 (11)0.0039 (7)0.0013 (8)0.0176 (8)
N10.0424 (9)0.0483 (9)0.0435 (9)0.0137 (7)0.0145 (7)0.0116 (7)
N20.0427 (9)0.0409 (8)0.0438 (9)0.0164 (7)0.0056 (7)0.0139 (7)
O10.0371 (7)0.0419 (7)0.0385 (7)0.0158 (5)0.0031 (5)0.0074 (5)
O20.0547 (8)0.0389 (7)0.0438 (7)0.0111 (6)0.0130 (6)0.0139 (6)
Geometric parameters (Å, º) top
C1—C101.365 (3)C19—C201.419 (3)
C1—C21.417 (3)C19—H190.9300
C1—C111.501 (3)C21—O21.334 (2)
C2—C31.405 (3)C21—C221.500 (3)
C2—C71.416 (3)C21—H21A0.9700
C3—C41.361 (2)C21—H21B0.9700
C3—H30.9300C22—C271.371 (3)
C4—C51.390 (3)C22—C231.371 (3)
C4—H40.9300C23—C241.394 (3)
C5—C61.357 (3)C23—H230.9300
C5—H50.9300C24—C251.371 (3)
C6—C71.405 (3)C24—H240.9300
C6—H60.9300C25—C261.379 (2)
C7—C81.395 (3)C25—C281.414 (2)
C8—C91.348 (3)C26—C271.376 (2)
C8—H80.9300C26—H260.9300
C9—C101.394 (3)C27—H270.9300
C9—H90.9300C28—N11.141 (2)
C10—O21.370 (2)C29—O11.443 (2)
C11—C121.372 (3)C29—C301.521 (3)
C11—C201.407 (3)C29—H29A0.9700
C12—O11.382 (2)C29—H29B0.9700
C12—C131.395 (3)C30—C351.372 (3)
C13—C141.350 (3)C30—C311.375 (3)
C13—H130.9300C31—C321.385 (3)
C14—C151.399 (3)C31—H310.9300
C14—H140.9300C32—C331.372 (3)
C15—C201.418 (3)C32—H320.9300
C15—C161.425 (3)C33—C341.377 (3)
C16—C171.337 (3)C33—C361.409 (3)
C16—H160.9300C34—C351.380 (3)
C17—C181.389 (3)C34—H340.9300
C17—H170.9300C35—H350.9300
C18—C191.374 (3)C36—N21.145 (2)
C18—H180.9300
C10—C1—C2118.37 (17)C20—C19—H19119.7
C10—C1—C11119.35 (17)C11—C20—C15120.10 (17)
C2—C1—C11122.22 (17)C11—C20—C19122.19 (18)
C3—C2—C7118.16 (17)C15—C20—C19117.71 (18)
C3—C2—C1122.21 (17)O2—C21—C22108.83 (15)
C7—C2—C1119.63 (17)O2—C21—H21A109.9
C4—C3—C2121.36 (18)C22—C21—H21A109.9
C4—C3—H3119.3O2—C21—H21B109.9
C2—C3—H3119.3C22—C21—H21B109.9
C3—C4—C5120.23 (17)H21A—C21—H21B108.3
C3—C4—H4119.9C27—C22—C23119.03 (18)
C5—C4—H4119.9C27—C22—C21121.88 (16)
C6—C5—C4120.26 (16)C23—C22—C21119.06 (17)
C6—C5—H5119.9C22—C23—C24119.97 (18)
C4—C5—H5119.9C22—C23—H23120.0
C5—C6—C7121.08 (17)C24—C23—H23120.0
C5—C6—H6119.5C25—C24—C23120.77 (17)
C7—C6—H6119.5C25—C24—H24119.6
C8—C7—C6122.47 (17)C23—C24—H24119.6
C8—C7—C2118.64 (18)C24—C25—C26118.77 (16)
C6—C7—C2118.89 (18)C24—C25—C28120.34 (16)
C9—C8—C7121.66 (18)C26—C25—C28120.87 (17)
C9—C8—H8119.2C27—C26—C25120.30 (17)
C7—C8—H8119.2C27—C26—H26119.9
C8—C9—C10119.44 (19)C25—C26—H26119.9
C8—C9—H9120.3C22—C27—C26121.12 (17)
C10—C9—H9120.3C22—C27—H27119.4
C1—C10—O2114.29 (16)C26—C27—H27119.4
C1—C10—C9122.25 (18)N1—C28—C25178.8 (2)
O2—C10—C9123.46 (17)O1—C29—C30111.64 (14)
C12—C11—C20118.51 (17)O1—C29—H29A109.3
C12—C11—C1121.18 (17)C30—C29—H29A109.3
C20—C11—C1120.18 (17)O1—C29—H29B109.3
C11—C12—O1115.20 (16)C30—C29—H29B109.3
C11—C12—C13121.56 (17)H29A—C29—H29B108.0
O1—C12—C13123.23 (16)C35—C30—C31118.23 (18)
C14—C13—C12120.16 (18)C35—C30—C29121.50 (17)
C14—C13—H13119.9C31—C30—C29120.24 (16)
C12—C13—H13119.9C30—C31—C32120.57 (17)
C13—C14—C15121.11 (18)C30—C31—H31119.7
C13—C14—H14119.4C32—C31—H31119.7
C15—C14—H14119.4C33—C32—C31120.76 (18)
C14—C15—C20118.51 (17)C33—C32—H32119.6
C14—C15—C16122.26 (18)C31—C32—H32119.6
C20—C15—C16119.23 (18)C32—C33—C34118.87 (18)
C17—C16—C15121.02 (18)C32—C33—C36121.13 (17)
C17—C16—H16119.5C34—C33—C36119.99 (17)
C15—C16—H16119.5C33—C34—C35119.96 (18)
C16—C17—C18120.58 (18)C33—C34—H34120.0
C16—C17—H17119.7C35—C34—H34120.0
C18—C17—H17119.7C30—C35—C34121.60 (18)
C19—C18—C17120.86 (18)C30—C35—H35119.2
C19—C18—H18119.6C34—C35—H35119.2
C17—C18—H18119.6N2—C36—C33178.20 (19)
C18—C19—C20120.55 (18)C12—O1—C29117.85 (13)
C18—C19—H19119.7C21—O2—C10124.00 (15)

Experimental details

Crystal data
Chemical formulaC36H24N2O2
Mr516.57
Crystal system, space groupTriclinic, 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)
V3)1348.0 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.30 × 0.26 × 0.24
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.97, 0.98
No. of measured, independent and
observed [I > 2σ(I)] reflections
12114, 5312, 4098
Rint0.033
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.112, 1.07
No. of reflections5312
No. of parameters361
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.13, 0.16

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 2000), SHELXTL (Bruker, 2000), SHELXTL.

 

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