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The title compound, C34H26N2O, (I), was synthesized by intermolecular [2+2] photo­cyclo­addition of trans-2-(2-phenyl­ethenyl)­benzoxazole and trans-4-(2-bi­phenyl­ethenyl)­pyridine in sulfuric acid solution. Compound (I), with an rctt stereo-structure, is the only crossed photo­cyclo­adduct in which the two hetero­aryl groups are situated opposite each other, which reveals that the cross-photodimerization process is a head-to-tail reaction rather than a head-to-head one. In (I), the cyclo­butane ring shows a puckered conformation and the two dihedral angles between the two triangles defined by diagonal lines of the cyclo­butane ring are 19.7 (2) and 19.8 (2)°. The four single bonds of the cyclo­butane ring are 1.558 (4), 1.545 (4), 1.572 (4) and 1.566 (4) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009418/ob6119sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009418/ob6119Isup2.hkl
Contains datablock I

CCDC reference: 189887

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.047
  • wR factor = 0.115
  • Data-to-parameter ratio = 13.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

r-1,c-2,t-3,t-4–1-(2-benzoxazolyl)-2-biphenyl-4-phenyl-3- pyridinylcyclobutane top
Crystal data top
C34H26N2OF(000) = 1008
Mr = 478.57Dx = 1.241 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.661 (5) ÅCell parameters from 93 reflections
b = 19.247 (7) Åθ = 2.3–24.7°
c = 11.010 (4) ŵ = 0.08 mm1
β = 107.273 (7)°T = 293 K
V = 2561.8 (16) Å3Plate, colorless
Z = 40.35 × 0.25 × 0.15 mm
Data collection top
Bruker CCD area-detector
diffractometer
4517 independent reflections
Radiation source: fine-focus sealed tube1891 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.082
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1514
Tmin = 0.974, Tmax = 0.989k = 2220
10446 measured reflectionsl = 1312
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.038P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.047(Δ/σ)max < 0.001
wR(F2) = 0.115Δρmax = 0.16 e Å3
S = 0.98Δρmin = 0.16 e Å3
4517 reflectionsExtinction correction: SHELXL97
335 parametersExtinction coefficient: 0.0023 (4)
0 restraints
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.

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*/UeqOcc. (<1)
O10.87292 (19)0.90551 (12)0.1137 (2)0.0540 (7)0.50
N1A0.87292 (19)0.90551 (12)0.1137 (2)0.0540 (7)0.50
N20.8346 (2)1.28815 (14)0.0255 (3)0.0629 (8)
N10.78546 (19)0.87502 (13)0.2529 (2)0.0595 (7)0.50
O1A0.78546 (19)0.87502 (13)0.2529 (2)0.0595 (7)0.50
C10.8093 (2)0.99903 (15)0.2248 (3)0.0449 (8)
H10.77891.00510.29620.054*
C20.9066 (2)1.05012 (14)0.2327 (3)0.0419 (8)
H20.90401.08790.29150.050*
C30.8477 (2)1.07406 (14)0.0953 (3)0.0427 (8)
H30.87761.04720.03740.051*
C40.7385 (2)1.03766 (14)0.1025 (3)0.0459 (8)
H40.71231.00470.03210.055*
C50.8259 (3)0.92571 (16)0.2008 (3)0.0505 (9)
C60.8618 (3)0.83397 (17)0.1102 (3)0.0494 (8)
C70.8953 (3)0.7853 (2)0.0375 (3)0.0723 (11)
H70.93440.79820.01830.087*
C80.8691 (3)0.7180 (2)0.0502 (4)0.0811 (12)
H80.89020.68420.00170.097*
C90.8124 (4)0.6987 (2)0.1331 (4)0.0838 (13)
H90.79490.65210.13880.101*
C100.7808 (3)0.7467 (2)0.2081 (4)0.0770 (12)
H100.74310.73370.26520.092*
C110.8076 (3)0.81485 (17)0.1947 (3)0.0516 (9)
C121.0231 (2)1.02363 (14)0.2637 (3)0.0387 (7)
C131.0917 (3)1.04226 (14)0.1924 (3)0.0469 (8)
H131.06511.07140.12260.056*
C141.1990 (3)1.01841 (14)0.2231 (3)0.0456 (8)
H141.24321.03210.17320.055*
C151.2436 (2)0.97474 (15)0.3259 (3)0.0411 (8)
C161.1735 (2)0.95591 (15)0.3978 (3)0.0483 (8)
H161.19960.92650.46730.058*
C171.0663 (2)0.98033 (16)0.3671 (3)0.0489 (8)
H171.02190.96740.41710.059*
C181.3561 (3)0.94607 (17)0.3537 (3)0.0452 (8)
C191.4403 (3)0.98439 (18)0.3288 (3)0.0644 (10)
H191.42651.02930.29710.077*
C201.5443 (3)0.9559 (3)0.3513 (4)0.0844 (13)
H201.59990.98180.33350.101*
C211.5670 (3)0.8908 (3)0.3986 (4)0.0865 (13)
H211.63730.87220.41210.104*
C221.4858 (3)0.8526 (2)0.4264 (3)0.0807 (12)
H221.50120.80830.46040.097*
C231.3811 (3)0.88034 (18)0.4037 (3)0.0624 (10)
H231.32640.85410.42260.075*
C240.6456 (2)1.08255 (15)0.1129 (3)0.0483 (8)
C250.6441 (3)1.11766 (16)0.2206 (3)0.0636 (10)
H250.70471.11480.29300.076*
C260.5538 (4)1.15730 (18)0.2236 (4)0.0845 (13)
H260.55371.18020.29790.101*
C270.4646 (3)1.1629 (2)0.1172 (6)0.0929 (15)
H270.40371.18950.11890.111*
C280.4657 (3)1.1295 (2)0.0098 (5)0.1088 (16)
H280.40561.13350.06300.131*
C290.5546 (3)1.08983 (19)0.0072 (4)0.0817 (12)
H290.55371.06720.06770.098*
C300.8444 (2)1.14866 (15)0.0578 (3)0.0418 (8)
C310.8907 (3)1.20190 (17)0.1389 (3)0.0554 (9)
H310.92681.19270.22400.066*
C320.8836 (3)1.26948 (18)0.0936 (4)0.0633 (10)
H320.91561.30430.15130.076*
C330.7899 (3)1.23608 (19)0.1024 (3)0.0673 (10)
H330.75361.24680.18690.081*
C340.7930 (3)1.16731 (17)0.0667 (3)0.0629 (10)
H340.76041.13350.12650.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0660 (18)0.0429 (15)0.0605 (17)0.0054 (13)0.0304 (14)0.0002 (13)
N1A0.0660 (18)0.0429 (15)0.0605 (17)0.0054 (13)0.0304 (14)0.0002 (13)
N20.071 (2)0.057 (2)0.056 (2)0.0052 (16)0.0112 (17)0.0032 (18)
N10.0540 (17)0.0627 (18)0.0642 (18)0.0046 (14)0.0211 (14)0.0096 (15)
O1A0.0540 (17)0.0627 (18)0.0642 (18)0.0046 (14)0.0211 (14)0.0096 (15)
C10.040 (2)0.053 (2)0.0403 (19)0.0039 (16)0.0107 (16)0.0034 (16)
C20.044 (2)0.0433 (19)0.0364 (19)0.0090 (16)0.0094 (15)0.0010 (15)
C30.044 (2)0.045 (2)0.0374 (19)0.0081 (15)0.0093 (15)0.0002 (15)
C40.046 (2)0.0488 (19)0.0380 (19)0.0032 (17)0.0052 (16)0.0034 (16)
C50.043 (2)0.047 (2)0.057 (2)0.0008 (17)0.0089 (18)0.0072 (19)
C60.048 (2)0.042 (2)0.054 (2)0.0041 (17)0.0103 (18)0.0047 (19)
C70.082 (3)0.063 (3)0.077 (3)0.001 (2)0.031 (2)0.010 (2)
C80.104 (4)0.054 (3)0.071 (3)0.014 (2)0.005 (3)0.005 (2)
C90.100 (4)0.049 (3)0.076 (3)0.008 (2)0.014 (3)0.010 (2)
C100.087 (3)0.064 (3)0.073 (3)0.016 (2)0.013 (2)0.016 (2)
C110.054 (2)0.043 (2)0.052 (2)0.0011 (18)0.0074 (18)0.0080 (18)
C120.040 (2)0.0399 (18)0.0353 (18)0.0020 (15)0.0098 (15)0.0020 (15)
C130.052 (2)0.0428 (19)0.045 (2)0.0054 (17)0.0133 (17)0.0081 (16)
C140.046 (2)0.0454 (19)0.048 (2)0.0012 (16)0.0173 (17)0.0023 (17)
C150.041 (2)0.0424 (19)0.0380 (19)0.0006 (15)0.0084 (16)0.0033 (16)
C160.045 (2)0.059 (2)0.0383 (19)0.0075 (17)0.0078 (17)0.0044 (17)
C170.043 (2)0.067 (2)0.0384 (19)0.0026 (17)0.0138 (16)0.0058 (17)
C180.041 (2)0.056 (2)0.0377 (19)0.0023 (18)0.0104 (16)0.0056 (17)
C190.047 (2)0.084 (3)0.062 (2)0.003 (2)0.0161 (19)0.006 (2)
C200.044 (3)0.137 (4)0.075 (3)0.007 (3)0.021 (2)0.013 (3)
C210.054 (3)0.132 (4)0.074 (3)0.033 (3)0.019 (2)0.008 (3)
C220.071 (3)0.084 (3)0.084 (3)0.029 (3)0.019 (3)0.009 (2)
C230.047 (2)0.067 (3)0.072 (3)0.0091 (19)0.0156 (19)0.003 (2)
C240.038 (2)0.048 (2)0.054 (2)0.0020 (16)0.0058 (17)0.0002 (18)
C250.059 (3)0.067 (2)0.061 (3)0.016 (2)0.013 (2)0.006 (2)
C260.092 (4)0.071 (3)0.100 (4)0.021 (3)0.044 (3)0.004 (2)
C270.047 (3)0.079 (3)0.153 (5)0.016 (2)0.028 (3)0.008 (3)
C280.050 (3)0.112 (4)0.133 (5)0.024 (3)0.021 (3)0.024 (3)
C290.057 (3)0.092 (3)0.076 (3)0.020 (2)0.012 (2)0.020 (2)
C300.038 (2)0.050 (2)0.037 (2)0.0055 (15)0.0099 (16)0.0025 (17)
C310.061 (2)0.053 (2)0.044 (2)0.0065 (18)0.0031 (18)0.0017 (19)
C320.066 (3)0.051 (2)0.063 (3)0.0023 (19)0.004 (2)0.006 (2)
C330.092 (3)0.063 (3)0.038 (2)0.010 (2)0.005 (2)0.007 (2)
C340.088 (3)0.051 (2)0.039 (2)0.0031 (19)0.003 (2)0.0023 (19)
Geometric parameters (Å, º) top
O1—C51.329 (3)C15—C181.472 (4)
O1—C61.384 (3)C16—C171.380 (4)
N2—C321.323 (4)C16—H160.9300
N2—C331.325 (4)C17—H170.9300
N1—C51.310 (3)C18—C231.379 (4)
N1—C111.392 (3)C18—C191.388 (4)
C1—C51.462 (4)C19—C201.380 (4)
C1—C21.558 (4)C19—H190.9300
C1—C41.566 (4)C20—C211.353 (5)
C1—H10.9800C20—H200.9300
C2—C121.502 (4)C21—C221.370 (5)
C2—C31.545 (4)C21—H210.9300
C2—H20.9800C22—C231.381 (4)
C3—C301.491 (4)C22—H220.9300
C3—C41.572 (4)C23—H230.9300
C3—H30.9800C24—C251.370 (4)
C4—C241.491 (4)C24—C291.381 (4)
C4—H40.9800C25—C261.382 (4)
C6—C111.360 (4)C25—H250.9300
C6—C71.378 (4)C26—C271.368 (5)
C7—C81.355 (4)C26—H260.9300
C7—H70.9300C27—C281.350 (5)
C8—C91.369 (5)C27—H270.9300
C8—H80.9300C28—C291.367 (5)
C9—C101.376 (5)C28—H280.9300
C9—H90.9300C29—H290.9300
C10—C111.373 (4)C30—C311.371 (4)
C10—H100.9300C30—C341.379 (4)
C12—C131.380 (3)C31—C321.386 (4)
C12—C171.385 (4)C31—H310.9300
C13—C141.378 (4)C32—H320.9300
C13—H130.9300C33—C341.378 (4)
C14—C151.388 (4)C33—H330.9300
C14—H140.9300C34—H340.9300
C15—C161.401 (4)
C5—O1—C6104.3 (3)C16—C15—C18121.4 (3)
C32—N2—C33114.4 (3)C17—C16—C15121.0 (3)
C5—N1—C11105.1 (3)C17—C16—H16119.5
C5—C1—C2117.8 (3)C15—C16—H16119.5
C5—C1—C4112.3 (2)C16—C17—C12121.7 (3)
C2—C1—C489.4 (2)C16—C17—H17119.1
C5—C1—H1111.8C12—C17—H17119.1
C2—C1—H1111.8C23—C18—C19117.8 (3)
C4—C1—H1111.8C23—C18—C15121.4 (3)
C12—C2—C3118.7 (2)C19—C18—C15120.8 (3)
C12—C2—C1120.4 (2)C20—C19—C18120.1 (3)
C3—C2—C189.4 (2)C20—C19—H19120.0
C12—C2—H2108.9C18—C19—H19120.0
C3—C2—H2108.9C21—C20—C19121.2 (4)
C1—C2—H2108.9C21—C20—H20119.4
C30—C3—C2121.6 (3)C19—C20—H20119.4
C30—C3—C4119.4 (2)C20—C21—C22119.7 (4)
C2—C3—C489.6 (2)C20—C21—H21120.2
C30—C3—H3108.2C22—C21—H21120.2
C2—C3—H3108.2C21—C22—C23119.7 (4)
C4—C3—H3108.2C21—C22—H22120.1
C24—C4—C1118.2 (2)C23—C22—H22120.1
C24—C4—C3118.1 (2)C18—C23—C22121.4 (3)
C1—C4—C388.2 (2)C18—C23—H23119.3
C24—C4—H4110.2C22—C23—H23119.3
C1—C4—H4110.2C25—C24—C29117.2 (3)
C3—C4—H4110.2C25—C24—C4124.5 (3)
N1—C5—O1114.5 (3)C29—C24—C4118.3 (3)
N1—C5—C1123.0 (3)C24—C25—C26121.1 (3)
O1—C5—C1122.1 (3)C24—C25—H25119.4
C11—C6—C7121.2 (3)C26—C25—H25119.4
C11—C6—O1108.6 (3)C27—C26—C25120.1 (4)
C7—C6—O1130.2 (3)C27—C26—H26120.0
C8—C7—C6117.6 (4)C25—C26—H26120.0
C8—C7—H7121.2C28—C27—C26119.5 (4)
C6—C7—H7121.2C28—C27—H27120.3
C7—C8—C9121.4 (4)C26—C27—H27120.3
C7—C8—H8119.3C27—C28—C29120.5 (4)
C9—C8—H8119.3C27—C28—H28119.8
C8—C9—C10121.4 (4)C29—C28—H28119.8
C8—C9—H9119.3C28—C29—C24121.7 (4)
C10—C9—H9119.3C28—C29—H29119.2
C11—C10—C9116.9 (4)C24—C29—H29119.2
C11—C10—H10121.6C31—C30—C34115.9 (3)
C9—C10—H10121.6C31—C30—C3124.6 (3)
C6—C11—C10121.5 (4)C34—C30—C3119.5 (3)
C6—C11—N1107.5 (3)C30—C31—C32119.8 (3)
C10—C11—N1130.9 (4)C30—C31—H31120.1
C13—C12—C17117.5 (3)C32—C31—H31120.1
C13—C12—C2121.6 (3)N2—C32—C31124.9 (3)
C17—C12—C2120.9 (3)N2—C32—H32117.5
C14—C13—C12121.0 (3)C31—C32—H32117.5
C14—C13—H13119.5N2—C33—C34125.0 (3)
C12—C13—H13119.5N2—C33—H33117.5
C13—C14—C15122.3 (3)C34—C33—H33117.5
C13—C14—H14118.9C33—C34—C30119.9 (3)
C15—C14—H14118.9C33—C34—H34120.1
C14—C15—C16116.4 (3)C30—C34—H34120.1
C14—C15—C18122.0 (3)
C5—C1—C2—C1222.3 (4)C12—C13—C14—C150.2 (4)
C4—C1—C2—C12137.4 (3)C13—C14—C15—C160.1 (4)
C5—C1—C2—C3101.0 (3)C13—C14—C15—C18176.3 (3)
C4—C1—C2—C314.0 (2)C14—C15—C16—C170.4 (4)
C12—C2—C3—C3096.4 (3)C18—C15—C16—C17176.7 (3)
C1—C2—C3—C30138.8 (3)C15—C16—C17—C120.7 (4)
C12—C2—C3—C4138.7 (3)C13—C12—C17—C160.6 (4)
C1—C2—C3—C414.0 (2)C2—C12—C17—C16179.5 (3)
C5—C1—C4—C24132.7 (3)C14—C15—C18—C23145.3 (3)
C2—C1—C4—C24107.4 (3)C16—C15—C18—C2330.8 (4)
C5—C1—C4—C3106.2 (3)C14—C15—C18—C1934.0 (4)
C2—C1—C4—C313.8 (2)C16—C15—C18—C19149.9 (3)
C30—C3—C4—C2419.4 (4)C23—C18—C19—C201.6 (5)
C2—C3—C4—C24107.3 (3)C15—C18—C19—C20177.7 (3)
C30—C3—C4—C1140.6 (3)C18—C19—C20—C210.6 (6)
C2—C3—C4—C113.9 (2)C19—C20—C21—C220.8 (6)
C11—N1—C5—O10.0 (4)C20—C21—C22—C231.2 (6)
C11—N1—C5—C1172.9 (3)C19—C18—C23—C221.2 (5)
C6—O1—C5—N10.3 (4)C15—C18—C23—C22178.1 (3)
C6—O1—C5—C1173.4 (3)C21—C22—C23—C180.2 (5)
C2—C1—C5—N1143.5 (3)C1—C4—C24—C2530.5 (4)
C4—C1—C5—N1114.8 (3)C3—C4—C24—C2573.7 (4)
C2—C1—C5—O144.0 (4)C1—C4—C24—C29149.7 (3)
C4—C1—C5—O157.7 (4)C3—C4—C24—C29106.1 (3)
C5—O1—C6—C110.6 (3)C29—C24—C25—C261.4 (5)
C5—O1—C6—C7180.0 (3)C4—C24—C25—C26178.8 (3)
C11—C6—C7—C82.1 (5)C24—C25—C26—C271.0 (6)
O1—C6—C7—C8177.3 (3)C25—C26—C27—C280.1 (6)
C6—C7—C8—C90.6 (6)C26—C27—C28—C290.6 (7)
C7—C8—C9—C100.9 (6)C27—C28—C29—C240.1 (7)
C8—C9—C10—C110.8 (6)C25—C24—C29—C280.9 (6)
C7—C6—C11—C102.2 (5)C4—C24—C29—C28179.3 (4)
O1—C6—C11—C10177.4 (3)C2—C3—C30—C310.7 (4)
C7—C6—C11—N1179.9 (3)C4—C3—C30—C31109.0 (3)
O1—C6—C11—N10.6 (4)C2—C3—C30—C34178.6 (3)
C9—C10—C11—C60.7 (5)C4—C3—C30—C3471.7 (4)
C9—C10—C11—N1178.1 (3)C34—C30—C31—C320.2 (4)
C5—N1—C11—C60.4 (3)C3—C30—C31—C32179.5 (3)
C5—N1—C11—C10177.3 (3)C33—N2—C32—C310.5 (5)
C3—C2—C12—C1323.7 (4)C30—C31—C32—N20.2 (5)
C1—C2—C12—C13131.6 (3)C32—N2—C33—C340.8 (5)
C3—C2—C12—C17157.5 (3)N2—C33—C34—C300.8 (5)
C1—C2—C12—C1749.6 (4)C31—C30—C34—C330.4 (5)
C17—C12—C13—C140.1 (4)C3—C30—C34—C33179.8 (3)
C2—C12—C13—C14179.0 (3)
 

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