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The title compound, C24H19N3O2, is an analogue of lophine and exhibits two-photon induced blue fluorescent emission. It adopts a distorted T-shape.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016946/wk6050sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016946/wk6050Isup2.hkl
Contains datablock I

CCDC reference: 277801

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.054
  • wR factor = 0.130
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 2
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C8 - C10 ... 1.44 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

4-[4,5-Bis(4-methoxyphenyl)-1H-imidazol-2-yl]benzonitrile top
Crystal data top
C24H19N3O2F(000) = 1600
Mr = 381.42Dx = 1.272 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4326 reflections
a = 9.801 (3) Åθ = 2.6–27.0°
b = 15.549 (4) ŵ = 0.08 mm1
c = 26.142 (7) ÅT = 273 K
V = 3984.1 (19) Å3Block, colorless
Z = 80.48 × 0.37 × 0.32 mm
Data collection top
Bruker SMART CCD 1K area-detector
diffractometer
2563 reflections with I > 2σ(I)
φ and ω scansRint = 0.041
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 27.1°, θmin = 2.6°
Tmin = 0.961, Tmax = 0.974h = 1212
17659 measured reflectionsk = 1919
4326 independent reflectionsl = 3318
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullOnly H-atom displacement parameters refined
R[F2 > 2σ(F2)] = 0.054 w = 1/[σ2(Fo2) + (0.0634P)2 + 2.2522P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.130(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.38 e Å3
4326 reflectionsΔρmin = 0.56 e Å3
261 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.1756 (2)0.30445 (13)0.00221 (6)0.0669 (6)
O2A0.5881 (4)0.4511 (3)0.1531 (2)0.0535 (16)*0.453 (10)
O2B0.5977 (3)0.4568 (2)0.1741 (2)0.0599 (14)*0.547 (10)
N10.03100 (18)0.16509 (12)0.22640 (6)0.0365 (4)
H1A0.10830.14140.21980.044*
N20.15676 (18)0.19979 (12)0.26803 (6)0.0375 (4)
N30.2246 (3)0.02281 (18)0.48686 (10)0.0870 (9)
C10.0502 (2)0.12506 (16)0.36298 (8)0.0426 (6)
H10.13120.15610.36470.051*
C20.0146 (2)0.11409 (14)0.31590 (7)0.0342 (5)
C30.0395 (2)0.15785 (14)0.27065 (8)0.0344 (5)
C40.1590 (2)0.23811 (14)0.22041 (8)0.0357 (5)
C50.0422 (2)0.21675 (14)0.19388 (8)0.0343 (5)
C60.1337 (2)0.06622 (15)0.31409 (9)0.0434 (6)
H60.17700.05720.28290.052*
C70.1890 (3)0.03175 (16)0.35818 (9)0.0477 (6)
H70.26950.00030.35650.057*
C80.1246 (3)0.04394 (15)0.40491 (8)0.0436 (6)
C90.0042 (3)0.09058 (16)0.40698 (9)0.0467 (6)
H90.03980.09860.43810.056*
C100.1822 (3)0.00799 (18)0.45080 (10)0.0578 (7)
C110.2726 (2)0.29387 (15)0.20442 (8)0.0386 (5)
C120.3309 (3)0.35160 (17)0.23854 (10)0.0514 (6)
H120.29730.35510.27180.062*
C130.4376 (3)0.40379 (18)0.22395 (12)0.0629 (8)
H130.47480.44190.24760.076*
C140.4902 (2)0.40073 (16)0.17515 (13)0.0615 (8)
C150.4324 (3)0.34407 (18)0.14061 (11)0.0585 (8)
H150.46560.34140.10730.070*
C160.3252 (2)0.29106 (16)0.15525 (10)0.0456 (6)
H160.28800.25300.13160.055*
C170.0113 (2)0.23867 (14)0.14317 (8)0.0353 (5)
C180.0015 (2)0.32100 (15)0.12327 (8)0.0412 (5)
H180.04280.36360.14190.049*
C190.0565 (2)0.34054 (16)0.07613 (9)0.0452 (6)
H190.04810.39590.06310.054*
C200.1239 (2)0.27831 (17)0.04820 (8)0.0441 (6)
C210.1337 (3)0.19588 (17)0.06687 (8)0.0482 (6)
H210.17760.15340.04800.058*
C220.0774 (2)0.17702 (16)0.11402 (8)0.0435 (6)
H220.08400.12120.12660.052*
C230.2822 (4)0.2570 (2)0.01908 (11)0.0846 (11)
H23A0.30840.28210.05110.127*
H23B0.35870.25730.00380.127*
H23C0.25270.19880.02460.127*
C24A0.6389 (7)0.4476 (4)0.1032 (2)0.060 (2)*0.453 (10)
H24A0.71000.48960.09930.090*0.453 (10)
H24B0.56670.45960.07950.090*0.453 (10)
H24C0.67500.39130.09670.090*0.453 (10)
C24B0.6769 (6)0.4419 (4)0.1306 (3)0.078 (2)*0.547 (10)
H24D0.75340.48050.13050.117*0.547 (10)
H24E0.62270.45140.10060.117*0.547 (10)
H24F0.70910.38360.13090.117*0.547 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0731 (13)0.0811 (14)0.0465 (10)0.0207 (11)0.0216 (9)0.0206 (10)
N10.0314 (9)0.0441 (11)0.0341 (10)0.0072 (8)0.0013 (7)0.0002 (8)
N20.0312 (10)0.0452 (11)0.0362 (10)0.0021 (9)0.0015 (8)0.0025 (8)
N30.123 (3)0.0772 (19)0.0605 (16)0.0118 (17)0.0285 (16)0.0173 (14)
C10.0370 (12)0.0502 (14)0.0406 (12)0.0026 (11)0.0040 (10)0.0034 (11)
C20.0306 (11)0.0363 (12)0.0357 (11)0.0029 (10)0.0005 (9)0.0023 (9)
C30.0312 (11)0.0390 (12)0.0330 (11)0.0004 (10)0.0004 (9)0.0003 (9)
C40.0319 (11)0.0400 (13)0.0350 (11)0.0009 (10)0.0026 (9)0.0004 (9)
C50.0313 (11)0.0388 (12)0.0330 (11)0.0023 (10)0.0031 (9)0.0008 (9)
C60.0443 (14)0.0446 (14)0.0412 (13)0.0043 (11)0.0032 (10)0.0023 (10)
C70.0472 (14)0.0429 (14)0.0531 (15)0.0111 (12)0.0033 (11)0.0063 (11)
C80.0549 (15)0.0368 (13)0.0393 (12)0.0024 (12)0.0084 (11)0.0053 (10)
C90.0529 (15)0.0514 (15)0.0358 (12)0.0000 (13)0.0041 (11)0.0038 (11)
C100.0739 (19)0.0497 (16)0.0499 (15)0.0016 (15)0.0118 (13)0.0092 (13)
C110.0295 (11)0.0409 (13)0.0455 (13)0.0006 (10)0.0027 (9)0.0063 (10)
C120.0471 (14)0.0529 (16)0.0543 (15)0.0068 (13)0.0078 (12)0.0037 (12)
C130.0485 (16)0.0516 (17)0.089 (2)0.0145 (14)0.0167 (15)0.0069 (15)
C140.0297 (13)0.0402 (15)0.115 (3)0.0059 (12)0.0046 (15)0.0234 (16)
C150.0431 (14)0.0549 (17)0.0774 (19)0.0078 (14)0.0225 (13)0.0215 (14)
C160.0369 (13)0.0468 (14)0.0531 (14)0.0026 (11)0.0057 (11)0.0059 (11)
C170.0312 (11)0.0434 (13)0.0313 (11)0.0017 (10)0.0018 (9)0.0004 (9)
C180.0389 (12)0.0427 (13)0.0419 (12)0.0048 (11)0.0024 (10)0.0030 (10)
C190.0457 (13)0.0436 (14)0.0462 (13)0.0021 (12)0.0017 (11)0.0087 (11)
C200.0416 (13)0.0569 (16)0.0337 (12)0.0058 (12)0.0014 (10)0.0070 (10)
C210.0547 (15)0.0542 (16)0.0357 (12)0.0168 (13)0.0063 (11)0.0017 (11)
C220.0502 (14)0.0429 (14)0.0375 (12)0.0103 (12)0.0003 (10)0.0046 (10)
C230.091 (2)0.106 (3)0.0569 (18)0.024 (2)0.0336 (17)0.0160 (18)
Geometric parameters (Å, º) top
O1—C201.367 (3)C11—C121.388 (3)
O1—C231.395 (3)C12—C131.378 (4)
O2A—C141.3663 (10)C12—H120.9300
O2A—C24A1.3961 (11)C13—C141.377 (4)
O2B—C141.3677 (10)C13—H130.9300
O2B—C24B1.3966 (11)C14—C151.383 (4)
N1—C31.352 (2)C15—C161.390 (3)
N1—C51.372 (3)C15—H150.9300
N1—H1A0.8600C16—H160.9300
N2—C31.323 (3)C17—C221.385 (3)
N2—C41.380 (3)C17—C181.385 (3)
N3—C101.136 (3)C18—C191.379 (3)
C1—C91.377 (3)C18—H180.9300
C1—C21.395 (3)C19—C201.381 (3)
C1—H10.9300C19—H190.9300
C2—C61.386 (3)C20—C211.375 (3)
C2—C31.464 (3)C21—C221.382 (3)
C4—C51.380 (3)C21—H210.9300
C4—C111.472 (3)C22—H220.9300
C5—C171.466 (3)C23—H23A0.9600
C6—C71.381 (3)C23—H23B0.9600
C6—H60.9300C23—H23C0.9600
C7—C81.388 (3)C24A—H24A0.9600
C7—H70.9300C24A—H24B0.9600
C8—C91.386 (3)C24A—H24C0.9600
C8—C101.439 (3)C24B—H24D0.9600
C9—H90.9300C24B—H24E0.9600
C11—C161.386 (3)C24B—H24F0.9600
C20—O1—C23118.1 (2)O2A—C14—C15112.1 (4)
C14—O2A—C24A128.5 (5)O2B—C14—C15135.2 (3)
C14—O2B—C24B109.7 (4)C13—C14—C15118.3 (2)
C3—N1—C5108.16 (17)C14—C15—C16120.5 (2)
C3—N1—H1A125.9C14—C15—H15119.7
C5—N1—H1A125.9C16—C15—H15119.7
C3—N2—C4105.87 (17)C11—C16—C15121.2 (3)
C9—C1—C2120.9 (2)C11—C16—H16119.4
C9—C1—H1119.6C15—C16—H16119.4
C2—C1—H1119.6C22—C17—C18117.7 (2)
C6—C2—C1118.6 (2)C22—C17—C5120.3 (2)
C6—C2—C3121.81 (19)C18—C17—C5122.0 (2)
C1—C2—C3119.4 (2)C19—C18—C17120.8 (2)
N2—C3—N1111.01 (18)C19—C18—H18119.6
N2—C3—C2125.83 (18)C17—C18—H18119.6
N1—C3—C2123.02 (19)C18—C19—C20120.4 (2)
C5—C4—N2109.63 (18)C18—C19—H19119.8
C5—C4—C11128.84 (19)C20—C19—H19119.8
N2—C4—C11121.52 (18)O1—C20—C21124.3 (2)
N1—C5—C4105.28 (18)O1—C20—C19115.8 (2)
N1—C5—C17120.63 (18)C21—C20—C19119.9 (2)
C4—C5—C17134.1 (2)C20—C21—C22119.1 (2)
C7—C6—C2120.7 (2)C20—C21—H21120.4
C7—C6—H6119.7C22—C21—H21120.4
C2—C6—H6119.7C21—C22—C17122.0 (2)
C6—C7—C8120.2 (2)C21—C22—H22119.0
C6—C7—H7119.9C17—C22—H22119.0
C8—C7—H7119.9O1—C23—H23A109.5
C9—C8—C7119.5 (2)O1—C23—H23B109.5
C9—C8—C10120.3 (2)H23A—C23—H23B109.5
C7—C8—C10120.1 (2)O1—C23—H23C109.5
C1—C9—C8120.1 (2)H23A—C23—H23C109.5
C1—C9—H9120.0H23B—C23—H23C109.5
C8—C9—H9120.0O2A—C24A—H24A109.5
N3—C10—C8177.5 (3)O2A—C24A—H24B109.5
C16—C11—C12117.6 (2)H24A—C24A—H24B109.5
C16—C11—C4121.8 (2)O2A—C24A—H24C109.5
C12—C11—C4120.6 (2)H24A—C24A—H24C109.5
C13—C12—C11121.0 (3)H24B—C24A—H24C109.5
C13—C12—H12119.5O2B—C24B—H24D109.5
C11—C12—H12119.5O2B—C24B—H24E109.5
C14—C13—C12121.4 (3)H24D—C24B—H24E109.5
C14—C13—H13119.3O2B—C24B—H24F109.5
C12—C13—H13119.3H24D—C24B—H24F109.5
O2A—C14—C13129.4 (4)H24E—C24B—H24F109.5
O2B—C14—C13106.5 (3)
C9—C1—C2—C61.3 (3)C11—C12—C13—C140.0 (4)
C9—C1—C2—C3174.7 (2)C24A—O2A—C14—O2B162.0 (10)
C4—N2—C3—N12.1 (2)C24A—O2A—C14—C13179.1 (5)
C4—N2—C3—C2173.7 (2)C24A—O2A—C14—C154.3 (6)
C5—N1—C3—N22.0 (2)C24B—O2B—C14—O2A29.9 (6)
C5—N1—C3—C2173.91 (19)C24B—O2B—C14—C13165.2 (4)
C6—C2—C3—N2175.1 (2)C24B—O2B—C14—C1511.9 (6)
C1—C2—C3—N29.1 (3)C12—C13—C14—O2A175.0 (3)
C6—C2—C3—N19.6 (3)C12—C13—C14—O2B177.2 (3)
C1—C2—C3—N1166.2 (2)C12—C13—C14—C150.5 (4)
C3—N2—C4—C51.4 (2)O2A—C14—C15—C16176.2 (3)
C3—N2—C4—C11177.4 (2)O2B—C14—C15—C16176.1 (3)
C3—N1—C5—C41.1 (2)C13—C14—C15—C160.8 (4)
C3—N1—C5—C17178.0 (2)C12—C11—C16—C150.1 (3)
N2—C4—C5—N10.2 (2)C4—C11—C16—C15180.0 (2)
C11—C4—C5—N1178.5 (2)C14—C15—C16—C110.5 (4)
N2—C4—C5—C17179.1 (2)N1—C5—C17—C2240.5 (3)
C11—C4—C5—C170.4 (4)C4—C5—C17—C22140.8 (3)
C1—C2—C6—C71.5 (3)N1—C5—C17—C18137.8 (2)
C3—C2—C6—C7174.4 (2)C4—C5—C17—C1841.0 (4)
C2—C6—C7—C80.7 (4)C22—C17—C18—C190.4 (3)
C6—C7—C8—C90.3 (4)C5—C17—C18—C19178.0 (2)
C6—C7—C8—C10180.0 (2)C17—C18—C19—C200.8 (4)
C2—C1—C9—C80.3 (4)C23—O1—C20—C2123.1 (4)
C7—C8—C9—C10.5 (4)C23—O1—C20—C19157.8 (3)
C10—C8—C9—C1179.8 (2)C18—C19—C20—O1179.4 (2)
C5—C4—C11—C1641.6 (3)C18—C19—C20—C211.5 (4)
N2—C4—C11—C16139.9 (2)O1—C20—C21—C22179.9 (2)
C5—C4—C11—C12138.3 (2)C19—C20—C21—C221.1 (4)
N2—C4—C11—C1240.2 (3)C20—C21—C22—C170.1 (4)
C16—C11—C12—C130.3 (4)C18—C17—C22—C210.8 (3)
C4—C11—C12—C13179.7 (2)C5—C17—C22—C21177.6 (2)
 

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