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The title compound, C34H32N4O2, undergoes a reversible [2+2] photoreaction with 1-(2-benzoxazol-2-yl)-2-bis­[4-(dimethyl­amino)phen­yl]ethane (NBE). Through inter­molecular head-to-tail [2+2] photocyclo­addition of NBE, the title compound displays a centrosymmetric mol­ecular structure in the crystalline state. The cyclo­butane ring has an exactly planar conformation and is nearly square.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004813/xu2195sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004813/xu2195Isup2.hkl
Contains datablock I

CCDC reference: 640525

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.064
  • wR factor = 0.218
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity.
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C10 - C15 .. 11.36 su
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

r-1,c-2,t-3,t-4–1,3-bis(N,N-dimethyl-4-benzenamino)-2,4-bis- (2-benzooxzolyl)cyclobutane top
Crystal data top
C34H32N4O2F(000) = 1120
Mr = 528.64Dx = 1.241 Mg m3
Monoclinic, C2/cMelting point: 548(1) K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 24.441 (5) ÅCell parameters from 12682 reflections
b = 6.0694 (12) Åθ = 2.3–25.0°
c = 20.101 (4) ŵ = 0.08 mm1
β = 108.46 (3)°T = 293 K
V = 2828.4 (10) Å3Platelet, colourless
Z = 40.44 × 0.35 × 0.21 mm
Data collection top
Rigaku R-AXIS RAPID image-plate
diffractometer
1549 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
ω scansh = 2828
12682 measured reflectionsk = 77
2476 independent reflectionsl = 2322
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1378P)2]
where P = (Fo2 + 2Fc2)/3
2476 reflections(Δ/σ)max < 0.001
183 parametersΔρmax = 0.32 e Å3
18 restraintsΔρmin = 0.41 e Å3
Special details top

Experimental. 1-(N,N-dimethyl-4-benzenamino)-2-(2-benzooxazolyl)ethane: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 7.76–7.26 (7H, m), 6.88–6.71 (3H, m), 3.03 (6H, s); 13C NMR (300 MHz, CDCl3, δ, p.p.m.): 163.2, 150.6, 149.6, 141.7, 139.2, 128.3, 124.1, 123.7, 118.6, 111.3, 109.3, 107.8, 39.5.

The title compound: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 7.65–7.18 (6H, m), 6.53 (2H, d), 4.93 (1H, t), 4.77 (1H, t), 2.80 (6H, s); 13C NMR (300 MHz, CDCl3, δ, p.p.m.): 165.1, 150.2, 148.7, 140.4, 127.3, 123.5, 123.0, 118.8, 111.8, 109.5, 43.1, 42.0, 39.8.

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*/Ueq
N10.12010 (11)0.8052 (4)0.42964 (14)0.0633 (7)
O10.14612 (9)1.1341 (4)0.47938 (11)0.0674 (6)
N20.36330 (13)0.8422 (5)0.24634 (14)0.0779 (9)
C10.08670 (12)1.1275 (5)0.45478 (15)0.0571 (8)
C20.04860 (16)1.2903 (7)0.4566 (2)0.0839 (11)
H2A0.06061.42710.47680.101*
C30.00897 (17)1.2375 (8)0.4265 (2)0.0902 (12)
H3A0.03671.34190.42680.108*
C40.02618 (16)1.0406 (8)0.3967 (2)0.0902 (12)
H4A0.06551.01240.37750.108*
C50.01267 (15)0.8786 (7)0.3937 (2)0.0877 (11)
H5A0.00060.74390.37200.105*
C60.07010 (13)0.9273 (5)0.42462 (15)0.0598 (8)
C70.16147 (12)0.9337 (5)0.46173 (14)0.0547 (7)
C80.22512 (12)0.8992 (5)0.48027 (14)0.0580 (8)
H8A0.24441.03380.47240.070*
C90.24309 (12)0.7011 (5)0.44503 (14)0.0560 (8)
H9A0.20900.61190.42170.067*
C100.27671 (11)0.7423 (5)0.39464 (14)0.0537 (7)
C110.27387 (14)0.5949 (6)0.34313 (17)0.0664 (9)
H11A0.25160.46870.33990.080*
C120.30281 (14)0.6255 (5)0.29555 (17)0.0675 (9)
H12A0.30000.51820.26160.081*
C130.33623 (12)0.8109 (5)0.29618 (13)0.0528 (7)
C140.34013 (13)0.9618 (5)0.34893 (16)0.0645 (8)
H14A0.36271.08730.35230.077*
C150.31056 (13)0.9282 (6)0.39711 (15)0.0666 (9)
H15A0.31361.03300.43180.080*
C160.3976 (2)1.0327 (8)0.2478 (2)0.1156 (17)
H16A0.37611.16200.25170.173*
H16B0.40761.04010.20540.173*
H16C0.43211.02470.28740.173*
C170.3640 (2)0.6713 (8)0.1978 (2)0.1190 (17)
H17A0.32590.61170.17830.179*
H17B0.38990.55680.22170.179*
H17C0.37670.73040.16090.179*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0584 (16)0.0588 (15)0.0689 (15)0.0188 (13)0.0146 (13)0.0009 (13)
O10.0541 (13)0.0771 (14)0.0686 (13)0.0112 (11)0.0159 (10)0.0074 (11)
N20.0839 (19)0.097 (2)0.0650 (16)0.0009 (17)0.0405 (15)0.0067 (15)
C10.0479 (17)0.074 (2)0.0506 (16)0.0117 (15)0.0171 (13)0.0014 (15)
C20.075 (2)0.088 (3)0.088 (2)0.025 (2)0.024 (2)0.012 (2)
C30.065 (2)0.114 (3)0.095 (3)0.041 (2)0.031 (2)0.014 (3)
C40.0455 (19)0.117 (3)0.102 (3)0.012 (2)0.0138 (19)0.022 (3)
C50.052 (2)0.090 (3)0.107 (3)0.0029 (19)0.0065 (19)0.004 (2)
C60.0522 (18)0.070 (2)0.0568 (17)0.0109 (16)0.0171 (14)0.0099 (16)
C70.0494 (17)0.0718 (19)0.0456 (15)0.0140 (16)0.0187 (13)0.0099 (15)
C80.0575 (18)0.0590 (16)0.0585 (17)0.0032 (14)0.0200 (14)0.0032 (14)
C90.0506 (16)0.0630 (18)0.0513 (15)0.0011 (14)0.0116 (13)0.0087 (14)
C100.0409 (14)0.0688 (18)0.0465 (14)0.0040 (14)0.0070 (11)0.0022 (14)
C110.067 (2)0.0685 (19)0.0654 (19)0.0003 (16)0.0230 (16)0.0077 (17)
C120.070 (2)0.073 (2)0.0643 (18)0.0007 (17)0.0280 (16)0.0183 (16)
C130.0476 (15)0.0653 (18)0.0449 (15)0.0118 (14)0.0141 (12)0.0010 (14)
C140.0579 (19)0.072 (2)0.0640 (18)0.0064 (16)0.0204 (15)0.0140 (17)
C150.0614 (19)0.086 (2)0.0489 (15)0.0082 (17)0.0133 (13)0.0220 (16)
C160.140 (4)0.129 (4)0.100 (3)0.037 (3)0.070 (3)0.002 (3)
C170.165 (5)0.124 (4)0.101 (3)0.007 (3)0.089 (3)0.033 (3)
Geometric parameters (Å, º) top
N1—C71.278 (4)C8—H8A0.9800
N1—C61.405 (4)C9—C101.514 (4)
O1—C71.353 (4)C9—C8i1.578 (4)
O1—C11.379 (4)C9—H9A0.9800
N2—C131.378 (4)C10—C111.354 (4)
N2—C161.423 (5)C10—C151.390 (4)
N2—C171.428 (5)C11—C121.370 (4)
C1—C61.361 (4)C11—H11A0.9300
C1—C21.366 (4)C12—C131.388 (4)
C2—C31.382 (6)C12—H12A0.9300
C2—H2A0.9300C13—C141.382 (4)
C3—C41.343 (6)C14—C151.395 (4)
C3—H3A0.9300C14—H14A0.9300
C4—C51.381 (5)C15—H15A0.9300
C4—H4A0.9300C16—H16A0.9600
C5—C61.375 (5)C16—H16B0.9600
C5—H5A0.9300C16—H16C0.9600
C7—C81.495 (4)C17—H17A0.9600
C8—C91.529 (4)C17—H17B0.9600
C8—C9i1.578 (4)C17—H17C0.9600
C7—N1—C6104.2 (3)C8—C9—C8i89.4 (2)
C7—O1—C1103.2 (2)C10—C9—H9A109.3
C13—N2—C16120.8 (3)C8—C9—H9A109.3
C13—N2—C17120.6 (3)C8i—C9—H9A109.3
C16—N2—C17118.1 (3)C11—C10—C15116.7 (3)
C6—C1—C2123.2 (3)C11—C10—C9119.7 (3)
C6—C1—O1108.5 (2)C15—C10—C9123.6 (3)
C2—C1—O1128.2 (3)C10—C11—C12122.1 (3)
C1—C2—C3115.4 (4)C10—C11—H11A119.0
C1—C2—H2A122.3C12—C11—H11A119.0
C3—C2—H2A122.3C11—C12—C13122.4 (3)
C4—C3—C2122.2 (3)C11—C12—H12A118.8
C4—C3—H3A118.9C13—C12—H12A118.8
C2—C3—H3A118.9N2—C13—C14122.3 (3)
C3—C4—C5122.0 (4)N2—C13—C12121.4 (3)
C3—C4—H4A119.0C14—C13—C12116.2 (3)
C5—C4—H4A119.0C13—C14—C15120.7 (3)
C6—C5—C4116.4 (4)C13—C14—H14A119.6
C6—C5—H5A121.8C15—C14—H14A119.6
C4—C5—H5A121.8C10—C15—C14121.8 (3)
C1—C6—C5120.7 (3)C10—C15—H15A119.1
C1—C6—N1108.0 (3)C14—C15—H15A119.1
C5—C6—N1131.3 (3)N2—C16—H16A109.5
N1—C7—O1116.1 (2)N2—C16—H16B109.5
N1—C7—C8129.4 (3)H16A—C16—H16B109.5
O1—C7—C8114.4 (3)N2—C16—H16C109.5
C7—C8—C9115.0 (3)H16A—C16—H16C109.5
C7—C8—C9i116.8 (2)H16B—C16—H16C109.5
C9—C8—C9i90.6 (2)N2—C17—H17A109.5
C7—C8—H8A111.0N2—C17—H17B109.5
C9—C8—H8A111.0H17A—C17—H17B109.5
C9i—C8—H8A111.0N2—C17—H17C109.5
C10—C9—C8118.4 (3)H17A—C17—H17C109.5
C10—C9—C8i119.5 (2)H17B—C17—H17C109.5
C7—O1—C1—C60.2 (3)C7—C8—C9—C10116.2 (3)
C7—O1—C1—C2177.8 (3)C9i—C8—C9—C10123.7 (3)
C6—C1—C2—C31.0 (5)C7—C8—C9—C8i120.2 (3)
O1—C1—C2—C3178.8 (3)C9i—C8—C9—C8i0.0
C1—C2—C3—C40.7 (6)C8—C9—C10—C11153.9 (3)
C2—C3—C4—C50.7 (6)C8i—C9—C10—C1199.1 (3)
C3—C4—C5—C61.7 (6)C8—C9—C10—C1525.1 (4)
C2—C1—C6—C50.1 (5)C8i—C9—C10—C1581.9 (4)
O1—C1—C6—C5178.1 (3)C15—C10—C11—C120.1 (5)
C2—C1—C6—N1177.6 (3)C9—C10—C11—C12179.1 (3)
O1—C1—C6—N10.6 (3)C10—C11—C12—C131.0 (5)
C4—C5—C6—C11.4 (5)C16—N2—C13—C140.9 (5)
C4—C5—C6—N1178.3 (3)C17—N2—C13—C14172.5 (4)
C7—N1—C6—C10.7 (3)C16—N2—C13—C12179.8 (4)
C7—N1—C6—C5177.8 (3)C17—N2—C13—C128.2 (5)
C6—N1—C7—O10.6 (3)C11—C12—C13—N2177.6 (3)
C6—N1—C7—C8177.6 (3)C11—C12—C13—C141.7 (5)
C1—O1—C7—N10.2 (3)N2—C13—C14—C15177.8 (3)
C1—O1—C7—C8177.7 (2)C12—C13—C14—C151.5 (4)
N1—C7—C8—C911.8 (4)C11—C10—C15—C140.1 (5)
O1—C7—C8—C9165.3 (2)C9—C10—C15—C14178.9 (3)
N1—C7—C8—C9i92.6 (3)C13—C14—C15—C100.7 (5)
O1—C7—C8—C9i90.3 (3)
Symmetry code: (i) x+1/2, y+3/2, z+1.
 

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