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The title compound, C34H28N4O4, is a derivative of di­phenyl­oxa­diazo­lylcyclo­butane (s-DPC), and although it is a syn-head-to-head photodimer, it does not display molecular mirror symmetry in the crystalline state. The cyclo­butane ring has a puckered conformation, with a dihedral angle of 30°, which is the largest among tetra­aryl-substituted cyclo­butanes reported so far. The four C-C single bonds of the cyclo­butane ring differ from each other. One is the same length as a typical C-C single bond, while the others are longer. The photodimerization of the corresponding monomer yields only 1% of s-DPC, suggesting that the head-to-head reaction is a minor photodimerization process.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017713/ww6038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017713/ww6038Isup2.hkl
Contains datablock I

CCDC reference: 200749

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.133
  • Data-to-parameter ratio = 13.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1998); 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-Bis(4-methoxyphenyl)-3,4-bis(5-phenyl-1,3,4- oxadiazol-2-yl)cyclobutane top
Crystal data top
C34H28N4O4Z = 2
Mr = 556.60F(000) = 584
Triclinic, P1Dx = 1.280 Mg m3
a = 9.1746 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3853 (10) ÅCell parameters from 5978 reflections
c = 14.5431 (12) Åθ = 1.5–25.0°
α = 91.648 (2)°µ = 0.09 mm1
β = 107.925 (2)°T = 298 K
γ = 91.642 (2)°Plate, colorless
V = 1443.6 (2) Å30.35 × 0.30 × 0.30 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3382 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.012
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
φ and ω scansh = 107
6052 measured reflectionsk = 1313
5079 independent reflectionsl = 1717
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0766P)2 + 0.0284P]
where P = (Fo2 + 2Fc2)/3
5079 reflections(Δ/σ)max < 0.001
388 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = 0.16 e Å3
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)
O10.50164 (12)0.37503 (9)0.19416 (9)0.0552 (3)
N10.71024 (18)0.44520 (14)0.30374 (13)0.0706 (5)
C10.6322 (2)0.23538 (14)0.31280 (13)0.0552 (5)
H1A0.73710.22390.35400.066*
O20.37046 (14)0.37125 (10)0.35694 (9)0.0609 (3)
C20.57560 (19)0.12783 (14)0.24310 (12)0.0521 (4)
H2A0.48650.15020.19020.062*
N20.64559 (19)0.53618 (13)0.24209 (13)0.0718 (5)
O30.93683 (19)0.24599 (12)0.54582 (11)0.0950 (5)
N30.24367 (18)0.22046 (14)0.26664 (13)0.0713 (5)
C30.5156 (2)0.07018 (15)0.32276 (13)0.0567 (5)
H3A0.41160.03540.29560.068*
N40.15029 (18)0.31896 (15)0.24854 (14)0.0734 (5)
C40.5160 (2)0.19590 (16)0.36706 (14)0.0595 (5)
H4A0.55900.20140.43770.071*
O40.9684 (2)0.11107 (17)0.07510 (14)0.1064 (6)
C50.62279 (19)0.35372 (15)0.27309 (13)0.0544 (5)
C60.5242 (2)0.49087 (14)0.17950 (14)0.0540 (4)
C70.3697 (2)0.25519 (16)0.32924 (14)0.0593 (5)
C80.2294 (2)0.40444 (16)0.30246 (14)0.0581 (5)
C90.9382 (3)0.36345 (18)0.51319 (17)0.0856 (7)
H9A1.01780.40330.55910.128*
H9B0.95680.36500.45170.128*
H9C0.84090.40210.50640.128*
C101.1249 (6)0.0921 (5)0.0994 (4)0.1022 (17)0.50
H10A1.16490.14400.06070.153*0.50
H10B1.17120.10720.16660.153*0.50
H10C1.14760.01200.08800.153*0.50
C10'0.9176 (9)0.1814 (7)0.0021 (7)0.174 (3)0.50
H10D0.80850.19230.01290.261*0.50
H10E0.96460.25570.01630.261*0.50
H10F0.94110.14940.05220.261*0.50
C110.6236 (2)0.01364 (15)0.38470 (13)0.0558 (5)
C120.6231 (2)0.12840 (15)0.35276 (14)0.0617 (5)
H12A0.55150.15310.29430.074*
C130.7242 (2)0.20894 (16)0.40350 (15)0.0657 (5)
H13A0.72010.28580.37910.079*
C140.8301 (2)0.17500 (16)0.48956 (14)0.0675 (5)
C150.8348 (3)0.06057 (18)0.52350 (16)0.0916 (8)
H15A0.90690.03620.58180.110*
C160.7332 (3)0.01805 (17)0.47159 (16)0.0835 (7)
H16A0.73850.09510.49580.100*
C210.6822 (2)0.06601 (14)0.19986 (12)0.0519 (4)
C220.6251 (2)0.01983 (17)0.12780 (15)0.0680 (5)
H22A0.52040.03830.10680.082*
C230.7195 (3)0.07921 (19)0.08594 (16)0.0783 (6)
H23A0.67830.13700.03760.094*
C240.8749 (3)0.05263 (18)0.11598 (16)0.0702 (6)
C250.9338 (2)0.03328 (18)0.18649 (15)0.0688 (5)
H25A1.03830.05250.20640.083*
C260.8387 (2)0.09148 (16)0.22821 (14)0.0621 (5)
H26A0.88060.14920.27650.074*
C310.4161 (2)0.54561 (15)0.09864 (13)0.0546 (5)
C320.4515 (3)0.65460 (17)0.07104 (16)0.0729 (6)
H32A0.54360.69370.10490.087*
C330.3509 (3)0.70593 (19)0.00667 (17)0.0821 (7)
H33A0.37580.77950.02500.098*
C340.2163 (3)0.6502 (2)0.05652 (17)0.0828 (7)
H34A0.14930.68500.10930.099*
C350.1795 (3)0.5426 (2)0.02887 (18)0.0956 (8)
H35A0.08640.50460.06240.115*
C360.2796 (2)0.4898 (2)0.04862 (17)0.0830 (7)
H36A0.25420.41630.06680.100*
C410.1906 (2)0.52707 (16)0.30812 (14)0.0577 (5)
C420.3027 (2)0.61386 (18)0.34783 (16)0.0714 (6)
H42A0.40450.59400.37370.086*
C430.2637 (3)0.72967 (19)0.34902 (18)0.0816 (6)
H43A0.33910.78820.37550.098*
C440.1131 (3)0.7587 (2)0.31096 (18)0.0834 (7)
H44A0.08680.83690.31200.100*
C450.0021 (3)0.6733 (2)0.27161 (18)0.0835 (7)
H45A0.09950.69350.24560.100*
C460.0400 (2)0.55800 (18)0.27043 (15)0.0712 (6)
H46A0.03620.50010.24410.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0530 (7)0.0464 (7)0.0586 (8)0.0042 (5)0.0058 (6)0.0047 (5)
N10.0632 (10)0.0516 (9)0.0803 (12)0.0037 (8)0.0026 (9)0.0024 (8)
C10.0519 (10)0.0478 (10)0.0575 (11)0.0124 (8)0.0038 (9)0.0008 (8)
O20.0615 (8)0.0567 (8)0.0612 (8)0.0172 (6)0.0127 (6)0.0006 (6)
C20.0535 (10)0.0465 (9)0.0486 (10)0.0086 (8)0.0039 (8)0.0032 (8)
N20.0670 (10)0.0490 (9)0.0839 (12)0.0017 (8)0.0002 (9)0.0048 (8)
O30.1270 (13)0.0580 (9)0.0730 (10)0.0388 (8)0.0117 (9)0.0001 (7)
N30.0591 (10)0.0588 (10)0.0920 (14)0.0104 (8)0.0168 (10)0.0021 (9)
C30.0585 (11)0.0500 (10)0.0585 (12)0.0101 (8)0.0127 (9)0.0063 (8)
N40.0566 (10)0.0637 (10)0.0947 (13)0.0126 (8)0.0150 (9)0.0006 (10)
C40.0656 (12)0.0557 (11)0.0535 (11)0.0174 (9)0.0112 (9)0.0057 (9)
O40.1210 (15)0.1124 (14)0.1014 (14)0.0254 (12)0.0570 (12)0.0118 (11)
C50.0474 (10)0.0497 (10)0.0585 (11)0.0091 (8)0.0046 (8)0.0020 (8)
C60.0551 (11)0.0427 (10)0.0636 (12)0.0048 (8)0.0175 (9)0.0018 (8)
C70.0638 (12)0.0551 (11)0.0609 (12)0.0135 (9)0.0208 (10)0.0055 (9)
C80.0504 (10)0.0612 (11)0.0624 (12)0.0126 (9)0.0159 (9)0.0056 (9)
C90.1187 (19)0.0547 (12)0.0763 (15)0.0317 (12)0.0167 (14)0.0103 (11)
C100.078 (3)0.141 (5)0.113 (4)0.036 (3)0.063 (3)0.018 (3)
C10'0.188 (8)0.153 (7)0.208 (9)0.004 (6)0.108 (7)0.070 (6)
C110.0644 (12)0.0488 (10)0.0539 (11)0.0112 (8)0.0166 (9)0.0070 (8)
C120.0688 (12)0.0513 (11)0.0582 (12)0.0041 (9)0.0094 (9)0.0016 (9)
C130.0813 (13)0.0439 (10)0.0671 (13)0.0118 (9)0.0148 (11)0.0023 (9)
C140.0885 (14)0.0514 (11)0.0545 (12)0.0231 (10)0.0077 (11)0.0068 (9)
C150.1205 (19)0.0637 (13)0.0620 (14)0.0336 (13)0.0157 (13)0.0071 (11)
C160.1155 (18)0.0517 (12)0.0637 (14)0.0307 (12)0.0032 (13)0.0049 (10)
C210.0581 (11)0.0458 (9)0.0468 (10)0.0071 (8)0.0079 (8)0.0075 (8)
C220.0682 (13)0.0679 (12)0.0659 (13)0.0063 (10)0.0194 (10)0.0075 (10)
C230.0969 (17)0.0689 (13)0.0708 (15)0.0079 (12)0.0313 (13)0.0180 (11)
C240.0824 (15)0.0663 (13)0.0710 (14)0.0118 (11)0.0360 (12)0.0064 (11)
C250.0636 (12)0.0697 (13)0.0716 (14)0.0088 (10)0.0180 (11)0.0034 (11)
C260.0624 (12)0.0556 (11)0.0609 (12)0.0083 (9)0.0081 (10)0.0003 (9)
C310.0554 (11)0.0530 (10)0.0572 (11)0.0102 (8)0.0189 (9)0.0067 (9)
C320.0785 (14)0.0561 (12)0.0779 (15)0.0056 (10)0.0140 (11)0.0105 (11)
C330.1010 (18)0.0639 (13)0.0794 (16)0.0149 (13)0.0225 (14)0.0195 (12)
C340.0858 (17)0.0927 (17)0.0680 (15)0.0274 (14)0.0167 (13)0.0254 (13)
C350.0704 (15)0.117 (2)0.0841 (17)0.0050 (14)0.0005 (12)0.0329 (15)
C360.0727 (14)0.0836 (15)0.0799 (16)0.0083 (12)0.0038 (12)0.0269 (12)
C410.0572 (11)0.0585 (11)0.0604 (12)0.0136 (9)0.0210 (9)0.0057 (9)
C420.0612 (12)0.0686 (13)0.0822 (15)0.0149 (10)0.0183 (11)0.0030 (11)
C430.0834 (16)0.0623 (13)0.1006 (18)0.0060 (12)0.0310 (14)0.0063 (12)
C440.0960 (18)0.0624 (13)0.0934 (18)0.0277 (13)0.0289 (14)0.0083 (12)
C450.0728 (14)0.0769 (15)0.0949 (17)0.0301 (12)0.0147 (13)0.0051 (13)
C460.0586 (12)0.0700 (13)0.0827 (15)0.0153 (10)0.0175 (11)0.0035 (11)
Geometric parameters (Å, º) top
O1—C61.3621 (19)C12—C131.383 (3)
O1—C51.3631 (19)C12—H12A0.9300
N1—C51.278 (2)C13—C141.364 (3)
N1—N21.411 (2)C13—H13A0.9300
C1—C51.475 (2)C14—C151.375 (3)
C1—C21.538 (2)C15—C161.376 (3)
C1—C41.572 (3)C15—H15A0.9300
C1—H1A0.9800C16—H16A0.9300
O2—C81.364 (2)C21—C221.379 (2)
O2—C71.369 (2)C21—C261.385 (2)
C2—C211.497 (2)C22—C231.383 (3)
C2—C31.579 (2)C22—H22A0.9300
C2—H2A0.9800C23—C241.378 (3)
N2—C61.285 (2)C23—H23A0.9300
O3—C141.368 (2)C24—C251.368 (3)
O3—C91.408 (2)C25—C261.380 (3)
N3—C71.276 (2)C25—H25A0.9300
N3—N41.412 (2)C26—H26A0.9300
C3—C111.503 (2)C31—C361.366 (3)
C3—C41.552 (2)C31—C321.376 (3)
C3—H3A0.9800C32—C331.378 (3)
N4—C81.286 (2)C32—H32A0.9300
C4—C71.476 (2)C33—C341.353 (3)
C4—H4A0.9800C33—H33A0.9300
O4—C10'1.269 (8)C34—C351.366 (3)
O4—C241.362 (3)C34—H34A0.9300
O4—C101.378 (5)C35—C361.382 (3)
C6—C311.454 (2)C35—H35A0.9300
C8—C411.457 (2)C36—H36A0.9300
C9—H9A0.9600C41—C461.381 (3)
C9—H9B0.9600C41—C421.382 (3)
C9—H9C0.9600C42—C431.377 (3)
C10—H10A0.9600C42—H42A0.9300
C10—H10B0.9600C43—C441.375 (3)
C10—H10C0.9600C43—H43A0.9300
C10'—H10D0.9600C44—C451.365 (3)
C10'—H10E0.9600C44—H44A0.9300
C10'—H10F0.9600C45—C461.369 (3)
C11—C121.373 (2)C45—H45A0.9300
C11—C161.382 (3)C46—H46A0.9300
C6—O1—C5103.09 (13)C11—C12—H12A118.5
C5—N1—N2106.55 (15)C13—C12—H12A118.5
C5—C1—C2119.08 (15)C14—C13—C12119.62 (17)
C5—C1—C4119.34 (14)C14—C13—H13A120.2
C2—C1—C488.40 (13)C12—C13—H13A120.2
C5—C1—H1A109.4C13—C14—O3125.08 (17)
C2—C1—H1A109.4C13—C14—C15119.01 (18)
C4—C1—H1A109.4O3—C14—C15115.90 (18)
C8—O2—C7102.63 (14)C14—C15—C16120.3 (2)
C21—C2—C1120.77 (15)C14—C15—H15A119.8
C21—C2—C3121.71 (14)C16—C15—H15A119.8
C1—C2—C388.14 (13)C15—C16—C11122.19 (19)
C21—C2—H2A108.1C15—C16—H16A118.9
C1—C2—H2A108.1C11—C16—H16A118.9
C3—C2—H2A108.1C22—C21—C26117.19 (18)
C6—N2—N1106.24 (14)C22—C21—C2119.83 (16)
C14—O3—C9117.95 (16)C26—C21—C2122.98 (16)
C7—N3—N4106.34 (16)C21—C22—C23121.72 (19)
C11—C3—C4116.45 (15)C21—C22—H22A119.1
C11—C3—C2114.27 (14)C23—C22—H22A119.1
C4—C3—C287.64 (13)C24—C23—C22119.9 (2)
C11—C3—H3A112.1C24—C23—H23A120.1
C4—C3—H3A112.1C22—C23—H23A120.1
C2—C3—H3A112.1O4—C24—C25120.5 (2)
C8—N4—N3106.36 (16)O4—C24—C23120.1 (2)
C7—C4—C3114.17 (16)C25—C24—C23119.44 (19)
C7—C4—C1110.68 (15)C24—C25—C26120.2 (2)
C3—C4—C187.89 (13)C24—C25—H25A119.9
C7—C4—H4A113.8C26—C25—H25A119.9
C3—C4—H4A113.8C25—C26—C21121.56 (19)
C1—C4—H4A113.8C25—C26—H26A119.2
C10'—O4—C24122.8 (4)C21—C26—H26A119.2
C10'—O4—C10111.7 (4)C36—C31—C32119.16 (19)
C24—O4—C10125.1 (3)C36—C31—C6120.95 (17)
N1—C5—O1112.13 (15)C32—C31—C6119.89 (17)
N1—C5—C1129.65 (17)C31—C32—C33120.2 (2)
O1—C5—C1118.17 (15)C31—C32—H32A119.9
N2—C6—O1111.99 (16)C33—C32—H32A119.9
N2—C6—C31129.02 (16)C34—C33—C32120.6 (2)
O1—C6—C31118.99 (15)C34—C33—H33A119.7
N3—C7—O2112.50 (16)C32—C33—H33A119.7
N3—C7—C4130.89 (18)C33—C34—C35119.6 (2)
O2—C7—C4116.21 (17)C33—C34—H34A120.2
N4—C8—O2112.16 (16)C35—C34—H34A120.2
N4—C8—C41129.04 (17)C34—C35—C36120.4 (2)
O2—C8—C41118.73 (17)C34—C35—H35A119.8
O3—C9—H9A109.5C36—C35—H35A119.8
O3—C9—H9B109.5C31—C36—C35120.1 (2)
H9A—C9—H9B109.5C31—C36—H36A120.0
O3—C9—H9C109.5C35—C36—H36A120.0
H9A—C9—H9C109.5C46—C41—C42119.23 (18)
H9B—C9—H9C109.5C46—C41—C8119.57 (18)
O4—C10—H10A109.5C42—C41—C8121.17 (17)
O4—C10—H10B109.5C43—C42—C41120.0 (2)
H10A—C10—H10B109.5C43—C42—H42A120.0
O4—C10—H10C109.5C41—C42—H42A120.0
H10A—C10—H10C109.5C44—C43—C42119.9 (2)
H10B—C10—H10C109.5C44—C43—H43A120.1
O4—C10'—H10D109.5C42—C43—H43A120.1
O4—C10'—H10E109.5C45—C44—C43120.3 (2)
H10D—C10'—H10E109.5C45—C44—H44A119.8
O4—C10'—H10F109.5C43—C44—H44A119.8
H10D—C10'—H10F109.5C44—C45—C46120.1 (2)
H10E—C10'—H10F109.5C44—C45—H45A120.0
C12—C11—C16115.86 (17)C46—C45—H45A120.0
C12—C11—C3119.77 (17)C45—C46—C41120.5 (2)
C16—C11—C3124.27 (16)C45—C46—H46A119.8
C11—C12—C13123.01 (18)C41—C46—H46A119.8
 

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