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In the title compound, C22H23BF2N2O, the styrene and boron-dipyrromethene (BODIPY) fused-ring fragments are almost coplanar. Short C-C bond lengths suggest some electronic conjugation between the two systems.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049336/hb2208sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049336/hb2208Isup2.hkl
Contains datablock I

CCDC reference: 629892

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.132
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C1 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C3 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C4 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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

4,4-Difluoro-3-[(4-methoxyphenyl)styryl]-1,5,7,8-tetramethyl-4-bora-3a,4a- diaza-s-indacene top
Crystal data top
C22H23BF2N2OZ = 2
Mr = 380.23F(000) = 400
Triclinic, P1Dx = 1.334 Mg m3
Hall symbol: -P 1Melting point: 192(1) K
a = 8.6442 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.0246 (3) ÅCell parameters from 3314 reflections
c = 12.0034 (3) Åθ = 2.3–32.1°
α = 64.565 (1)°µ = 0.10 mm1
β = 73.311 (2)°T = 298 K
γ = 68.007 (1)°Cube, dark-blue
V = 946.90 (4) Å30.60 × 0.60 × 0.60 mm
Data collection top
Bruker SMART APEX-II CCD
diffractometer
2915 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
Detector resolution: 9.81 pixels mm-1h = 1010
φ and ω scansk = 1313
11471 measured reflectionsl = 1414
3314 independent reflections
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) = 0.132H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0798P)2 + 0.1878P]
where P = (Fo2 + 2Fc2)/3
3314 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

Experimental. Mp.: 465 K; 1H NMR (CDCl3): δ 7.531(d, 2H), 7.512 (d, 2H, J = 16.4 Hz), 7.185 (d, 2H, J = 16.4 Hz), 6.895 (d, 2H), 6.667 (s, 1H), 6.075 (s, 1H), 3.840 (s, 3H), 2.612(s, 3H), 2.558 (s, 3H), 2.473 (s, 3H), 2.434(s, 3H). HRMS(EI): 380.1874, calculated: 380.1872.

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
N20.36476 (16)0.67075 (14)0.19591 (12)0.0413 (3)
F20.10390 (11)0.65366 (11)0.17985 (10)0.0558 (3)
F10.17586 (13)0.56574 (11)0.37107 (9)0.0559 (3)
N10.33360 (15)0.44167 (14)0.23143 (12)0.0400 (3)
C220.53238 (19)0.62762 (18)0.14186 (14)0.0416 (4)
C210.50183 (19)0.40301 (17)0.17676 (14)0.0407 (4)
C200.2675 (2)0.33585 (17)0.26462 (15)0.0422 (4)
C190.59970 (19)0.49473 (17)0.13254 (14)0.0421 (4)
C180.4596 (2)0.19315 (17)0.52047 (15)0.0445 (4)
C170.1409 (2)0.22971 (16)0.40255 (14)0.0412 (4)
C160.5384 (2)0.26409 (18)0.17899 (15)0.0449 (4)
C150.6018 (2)0.73986 (19)0.10410 (15)0.0480 (4)
C140.1788 (2)0.10801 (17)0.42635 (16)0.0463 (4)
H14A0.09590.03720.40200.056*
C130.0945 (2)0.34170 (17)0.32130 (15)0.0454 (4)
H13A0.02660.41960.34200.054*
C120.3342 (2)0.08877 (18)0.48446 (17)0.0484 (4)
H12A0.35500.00580.49950.058*
O0.60802 (16)0.16346 (14)0.57983 (14)0.0629 (4)
C110.3309 (2)0.80130 (18)0.19290 (16)0.0473 (4)
C100.0283 (2)0.24025 (17)0.34520 (15)0.0446 (4)
H10A0.10090.16530.32180.053*
C90.4754 (2)0.8453 (2)0.13713 (17)0.0536 (4)
H9A0.48500.93180.12430.064*
B0.2385 (2)0.58434 (19)0.24703 (17)0.0403 (4)
C80.3939 (2)0.22544 (18)0.23256 (16)0.0472 (4)
H8A0.38090.14000.24580.057*
C70.4275 (2)0.31659 (18)0.49603 (18)0.0526 (4)
H7A0.51170.38780.51900.063*
C60.2705 (2)0.33435 (18)0.43756 (18)0.0504 (4)
H6A0.25080.41820.42110.060*
C50.7799 (2)0.4522 (2)0.07340 (18)0.0574 (5)
H5A0.80790.35920.07350.086*
H5B0.85270.45330.11980.086*
H5C0.79420.51670.01090.086*
C40.7756 (2)0.7516 (2)0.0404 (2)0.0656 (5)
H4A0.78240.84160.02770.098*
H4B0.79780.74160.03880.098*
H4C0.85750.67890.09150.098*
C30.1633 (3)0.8809 (2)0.2414 (2)0.0632 (5)
H3A0.08750.82420.27470.095*
H3B0.11890.96530.17480.095*
H3C0.17530.90470.30600.095*
C20.7436 (2)0.2661 (2)0.6177 (2)0.0607 (5)
H2A0.83900.23030.65820.091*
H2B0.77350.34920.54580.091*
H2C0.71030.28840.67460.091*
C10.6989 (2)0.1702 (2)0.13461 (19)0.0601 (5)
H1A0.68120.08320.14960.090*
H1B0.78630.15210.17900.090*
H1C0.73180.21530.04680.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0339 (7)0.0473 (7)0.0418 (7)0.0128 (6)0.0013 (5)0.0173 (6)
F20.0353 (5)0.0575 (6)0.0745 (7)0.0075 (4)0.0140 (5)0.0252 (5)
F10.0605 (6)0.0617 (6)0.0476 (6)0.0276 (5)0.0139 (5)0.0273 (5)
N10.0312 (7)0.0473 (7)0.0416 (7)0.0120 (5)0.0014 (5)0.0183 (6)
C220.0305 (7)0.0559 (9)0.0379 (8)0.0144 (7)0.0027 (6)0.0164 (7)
C210.0310 (7)0.0517 (9)0.0368 (8)0.0082 (6)0.0033 (6)0.0179 (6)
C200.0389 (8)0.0470 (9)0.0420 (8)0.0138 (7)0.0045 (6)0.0172 (7)
C190.0319 (8)0.0565 (9)0.0352 (8)0.0116 (7)0.0034 (6)0.0163 (7)
C180.0400 (9)0.0470 (9)0.0503 (9)0.0179 (7)0.0023 (7)0.0194 (7)
C170.0403 (8)0.0436 (8)0.0423 (8)0.0141 (7)0.0048 (6)0.0173 (6)
C160.0405 (9)0.0510 (9)0.0392 (8)0.0067 (7)0.0047 (6)0.0192 (7)
C150.0403 (9)0.0634 (10)0.0430 (9)0.0233 (8)0.0045 (7)0.0157 (8)
C140.0413 (9)0.0454 (9)0.0575 (10)0.0110 (7)0.0037 (7)0.0271 (8)
C130.0390 (8)0.0471 (9)0.0512 (9)0.0137 (7)0.0017 (7)0.0209 (7)
C120.0459 (9)0.0435 (9)0.0642 (10)0.0189 (7)0.0048 (8)0.0241 (8)
O0.0441 (7)0.0599 (8)0.0889 (10)0.0259 (6)0.0116 (6)0.0354 (7)
C110.0445 (9)0.0489 (9)0.0492 (9)0.0164 (7)0.0027 (7)0.0187 (7)
C100.0405 (8)0.0470 (9)0.0483 (9)0.0130 (7)0.0027 (7)0.0214 (7)
C90.0552 (11)0.0540 (10)0.0571 (10)0.0261 (8)0.0033 (8)0.0197 (8)
B0.0305 (8)0.0467 (10)0.0438 (9)0.0113 (7)0.0003 (7)0.0198 (7)
C80.0472 (9)0.0457 (9)0.0498 (9)0.0136 (7)0.0043 (7)0.0203 (7)
C70.0424 (9)0.0456 (9)0.0721 (12)0.0138 (7)0.0050 (8)0.0312 (8)
C60.0471 (9)0.0411 (8)0.0672 (11)0.0196 (7)0.0026 (8)0.0247 (8)
C50.0363 (9)0.0695 (12)0.0624 (11)0.0153 (8)0.0063 (8)0.0290 (9)
C40.0481 (11)0.0841 (14)0.0702 (13)0.0359 (10)0.0008 (9)0.0251 (11)
C30.0569 (11)0.0519 (10)0.0771 (13)0.0163 (9)0.0060 (9)0.0296 (9)
C20.0424 (10)0.0654 (11)0.0683 (12)0.0171 (8)0.0054 (8)0.0261 (9)
C10.0500 (11)0.0595 (11)0.0622 (11)0.0041 (8)0.0015 (8)0.0305 (9)
Geometric parameters (Å, º) top
N2—C111.343 (2)C13—C101.330 (2)
N2—C221.398 (2)C13—H13A0.9300
N2—B1.538 (2)C12—H12A0.9300
F2—B1.390 (2)O—C21.415 (2)
F1—B1.382 (2)C11—C91.392 (2)
N1—C201.348 (2)C11—C31.486 (3)
N1—C211.3982 (19)C10—H10A0.9300
N1—B1.543 (2)C9—H9A0.9300
C22—C191.401 (2)C8—H8A0.9300
C22—C151.420 (2)C7—C61.380 (2)
C21—C191.393 (2)C7—H7A0.9300
C21—C161.433 (2)C6—H6A0.9300
C20—C81.410 (2)C5—H5A0.9600
C20—C131.444 (2)C5—H5B0.9600
C19—C51.501 (2)C5—H5C0.9600
C18—O1.360 (2)C4—H4A0.9600
C18—C71.381 (2)C4—H4B0.9600
C18—C121.382 (2)C4—H4C0.9600
C17—C141.391 (2)C3—H3A0.9600
C17—C61.393 (2)C3—H3B0.9600
C17—C101.452 (2)C3—H3C0.9600
C16—C81.363 (2)C2—H2A0.9600
C16—C11.501 (2)C2—H2B0.9600
C15—C91.378 (3)C2—H2C0.9600
C15—C41.503 (2)C1—H1A0.9600
C14—C121.373 (2)C1—H1B0.9600
C14—H14A0.9300C1—H1C0.9600
C11—N2—C22108.83 (13)C15—C9—H9A125.6
C11—N2—B125.63 (14)C11—C9—H9A125.6
C22—N2—B125.52 (13)F1—B—F2108.36 (13)
C20—N1—C21108.88 (13)F1—B—N2110.70 (13)
C20—N1—B125.84 (13)F2—B—N2109.93 (13)
C21—N1—B125.25 (13)F1—B—N1110.72 (13)
N2—C22—C19120.36 (14)F2—B—N1109.94 (13)
N2—C22—C15107.21 (14)N2—B—N1107.20 (12)
C19—C22—C15132.43 (15)C16—C8—C20108.98 (15)
C19—C21—N1120.69 (15)C16—C8—H8A125.5
C19—C21—C16132.22 (15)C20—C8—H8A125.5
N1—C21—C16107.09 (14)C6—C7—C18120.07 (16)
N1—C20—C8108.32 (14)C6—C7—H7A120.0
N1—C20—C13123.63 (14)C18—C7—H7A120.0
C8—C20—C13128.04 (15)C7—C6—C17121.61 (15)
C21—C19—C22120.95 (14)C7—C6—H6A119.2
C21—C19—C5120.12 (15)C17—C6—H6A119.2
C22—C19—C5118.93 (15)C19—C5—H5A109.5
O—C18—C7124.93 (15)C19—C5—H5B109.5
O—C18—C12115.60 (14)H5A—C5—H5B109.5
C7—C18—C12119.47 (15)C19—C5—H5C109.5
C14—C17—C6116.73 (14)H5A—C5—H5C109.5
C14—C17—C10119.19 (14)H5B—C5—H5C109.5
C6—C17—C10124.07 (14)C15—C4—H4A109.5
C8—C16—C21106.72 (14)C15—C4—H4B109.5
C8—C16—C1122.95 (16)H4A—C4—H4B109.5
C21—C16—C1130.33 (16)C15—C4—H4C109.5
C9—C15—C22106.41 (14)H4A—C4—H4C109.5
C9—C15—C4123.50 (17)H4B—C4—H4C109.5
C22—C15—C4130.09 (17)C11—C3—H3A109.5
C12—C14—C17122.31 (15)C11—C3—H3B109.5
C12—C14—H14A118.8H3A—C3—H3B109.5
C17—C14—H14A118.8C11—C3—H3C109.5
C10—C13—C20122.69 (15)H3A—C3—H3C109.5
C10—C13—H13A118.7H3B—C3—H3C109.5
C20—C13—H13A118.7O—C2—H2A109.5
C14—C12—C18119.78 (15)O—C2—H2B109.5
C14—C12—H12A120.1H2A—C2—H2B109.5
C18—C12—H12A120.1O—C2—H2C109.5
C18—O—C2118.96 (14)H2A—C2—H2C109.5
N2—C11—C9108.68 (15)H2B—C2—H2C109.5
N2—C11—C3123.49 (15)C16—C1—H1A109.5
C9—C11—C3127.83 (16)C16—C1—H1B109.5
C13—C10—C17129.31 (15)H1A—C1—H1B109.5
C13—C10—H10A115.3C16—C1—H1C109.5
C17—C10—H10A115.3H1A—C1—H1C109.5
C15—C9—C11108.87 (16)H1B—C1—H1C109.5
C11—N2—C22—C19179.57 (14)C7—C18—O—C21.7 (3)
B—N2—C22—C191.2 (2)C12—C18—O—C2178.89 (16)
C11—N2—C22—C150.23 (17)C22—N2—C11—C90.05 (19)
B—N2—C22—C15178.19 (14)B—N2—C11—C9178.46 (15)
C20—N1—C21—C19179.29 (14)C22—N2—C11—C3179.31 (17)
B—N1—C21—C191.1 (2)B—N2—C11—C30.9 (3)
C20—N1—C21—C160.68 (17)C20—C13—C10—C17179.17 (16)
B—N1—C21—C16178.90 (13)C14—C17—C10—C13175.48 (17)
C21—N1—C20—C80.55 (17)C6—C17—C10—C133.7 (3)
B—N1—C20—C8178.75 (14)C22—C15—C9—C110.5 (2)
C21—N1—C20—C13178.55 (15)C4—C15—C9—C11179.40 (16)
B—N1—C20—C130.3 (2)N2—C11—C9—C150.3 (2)
N1—C21—C19—C220.1 (2)C3—C11—C9—C15179.01 (18)
C16—C21—C19—C22179.93 (15)C11—N2—B—F159.0 (2)
N1—C21—C19—C5179.66 (15)C22—N2—B—F1122.82 (16)
C16—C21—C19—C50.3 (3)C11—N2—B—F260.7 (2)
N2—C22—C19—C210.1 (2)C22—N2—B—F2117.49 (16)
C15—C22—C19—C21179.22 (16)C11—N2—B—N1179.87 (14)
N2—C22—C19—C5179.70 (14)C22—N2—B—N12.0 (2)
C15—C22—C19—C50.5 (3)C20—N1—B—F159.3 (2)
C19—C21—C16—C8179.41 (17)C21—N1—B—F1122.77 (15)
N1—C21—C16—C80.55 (17)C20—N1—B—F260.4 (2)
C19—C21—C16—C10.9 (3)C21—N1—B—F2117.53 (15)
N1—C21—C16—C1179.13 (17)C20—N1—B—N2179.85 (13)
N2—C22—C15—C90.42 (18)C21—N1—B—N21.9 (2)
C19—C22—C15—C9179.65 (17)C21—C16—C8—C200.23 (18)
N2—C22—C15—C4179.43 (17)C1—C16—C8—C20179.48 (16)
C19—C22—C15—C40.2 (3)N1—C20—C8—C160.19 (19)
C6—C17—C14—C121.7 (3)C13—C20—C8—C16178.86 (16)
C10—C17—C14—C12177.55 (16)O—C18—C7—C6178.50 (18)
N1—C20—C13—C10175.05 (16)C12—C18—C7—C60.9 (3)
C8—C20—C13—C103.9 (3)C18—C7—C6—C170.4 (3)
C17—C14—C12—C180.5 (3)C14—C17—C6—C71.7 (3)
O—C18—C12—C14178.59 (16)C10—C17—C6—C7177.55 (17)
C7—C18—C12—C140.8 (3)
 

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