Literature DB >> 21754182

4-(4,4-Difluoro-1,3,5,7-tetra-methyl-3a-aza-4a-azonia-4-borata-s-indacen-8-yl)benzonitrile.

Yuting Chen, Jianzhuang Jiang.   

Abstract

The title compound, C(20)H(18)BF(2)N(3), contains one C(9)BN(2) (Bodipy) framework and one cyano-benzyl group. The Bodipy framework is essentially planar with a maximum deviation of 0.041 (2) Å. The introduction of two methyl groups at positions 1 and 7 of s-indacene in the Bodipy unit results in almost orthogonal configuration between the mean plane of the Bodipy unit and the cyano-benzyl group [dihedral angle = 89.78 (4)°].

Entities:  

Year:  2011        PMID： 21754182      PMCID： PMC3100033          DOI： 10.1107/S1600536811009457

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the structures and optical properties of Bodipy dyes, see: Loudet & Burgess (2007 ▶) and Feng et al. (2008 ▶), respectively. For the relation between the crystal structures and optical properties of Bodipy compounds, see: Cui et al. (2007 ▶); Broring et al.(2008 ▶).

Experimental

Crystal data

C20H18BF2N3 M = 349.18 Monoclinic, a = 7.6498 (3) Å b = 11.3715 (5) Å c = 21.555 (1) Å β = 92.008 (4)° V = 1873.91 (14) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 293 K 0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.983, T max = 0.986 7304 measured reflections 3286 independent reflections 2240 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.065 wR(F 2) = 0.195 S = 1.07 3286 reflections 235 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.25 e Å−3 Data collection: SMART (Bruker, 1996 ▶); cell refinement: SAINT (Bruker, 1996 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811009457/aa2003sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009457/aa2003Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H18BF2N3F(000) = 728
Mr = 349.18Dx = 1.238 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3286 reflections
a = 7.6498 (3) Åθ = 2.3–25.0°
b = 11.3715 (5) ŵ = 0.09 mm−1
c = 21.555 (1) ÅT = 293 K
β = 92.008 (4)°Block, red
V = 1873.91 (14) Å30.20 × 0.18 × 0.16 mm
Z = 4
Bruker SMART 1000 CCD area-detector diffractometer3286 independent reflections
Radiation source: fine-focus sealed tube2240 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→8
Tmin = 0.983, Tmax = 0.986k = −13→13
7304 measured reflectionsl = −25→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1059P)2 + 0.276P] where P = (Fo2 + 2Fc2)/3
3286 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.
xyzUiso*/Ueq
F20.6736 (2)1.18071 (15)0.82647 (9)0.0706 (6)
N10.7514 (3)0.97876 (19)0.81048 (9)0.0409 (6)
F10.8040 (3)1.13260 (16)0.73783 (8)0.0750 (6)
N20.9776 (3)1.13074 (18)0.83306 (9)0.0384 (5)
C171.2845 (4)0.6972 (2)0.99641 (13)0.0491 (7)
C81.0075 (3)0.9342 (2)0.87582 (11)0.0376 (6)
C141.1043 (3)0.8502 (2)0.91690 (12)0.0391 (6)
C101.0737 (3)1.0468 (2)0.86812 (11)0.0388 (6)
C90.8499 (3)0.8989 (2)0.84668 (11)0.0405 (6)
C201.3795 (5)0.6205 (3)1.03874 (14)0.0619 (9)
C181.1552 (4)0.7687 (3)1.01831 (13)0.0623 (9)
H181.12930.76671.06010.075*
C161.3223 (4)0.7006 (3)0.93441 (14)0.0593 (8)
H161.40780.65130.91910.071*
C151.2329 (4)0.7774 (3)0.89494 (13)0.0555 (8)
H151.25950.78010.85320.067*
C21.2232 (4)1.2167 (3)0.86865 (14)0.0548 (8)
H21.30841.27390.87580.066*
C50.6123 (3)0.9205 (3)0.78539 (13)0.0495 (7)
C191.0646 (4)0.8426 (3)0.97863 (13)0.0579 (8)
H190.97480.88850.99360.069*
C40.9998 (4)1.3421 (3)0.80490 (16)0.0627 (9)
H4A0.88931.32660.78400.094*
H4B1.08141.37010.77540.094*
H4C0.98491.40080.83630.094*
C11.2306 (3)1.1032 (3)0.89043 (13)0.0484 (7)
C70.7648 (4)0.7874 (2)0.84295 (14)0.0510 (7)
C60.6190 (4)0.8041 (3)0.80502 (15)0.0588 (8)
H30.53730.74650.79420.071*
C31.0675 (4)1.2325 (2)0.83408 (12)0.0461 (7)
B10.7971 (4)1.1087 (3)0.80066 (14)0.0441 (8)
C110.8200 (5)0.6725 (3)0.87155 (19)0.0788 (11)
H5A0.92510.68360.89650.118*
H5B0.84110.61640.83930.118*
H5C0.72900.64380.89710.118*
C131.3786 (4)1.0532 (3)0.92990 (17)0.0722 (10)
H13A1.35440.97240.93920.108*
H13B1.39071.09710.96790.108*
H13C1.48521.05820.90780.108*
C120.4752 (4)0.9784 (3)0.74490 (17)0.0751 (10)
H1A0.50451.05980.73950.113*
H1B0.36400.97250.76400.113*
H1C0.46900.94020.70520.113*
N31.4528 (4)0.5619 (3)1.07363 (14)0.0836 (10)
U11U22U33U12U13U23
F20.0473 (9)0.0506 (10)0.1138 (16)0.0101 (8)0.0003 (10)−0.0057 (10)
N10.0394 (11)0.0438 (13)0.0393 (12)−0.0006 (10)−0.0026 (9)0.0010 (10)
F10.0938 (14)0.0822 (13)0.0473 (11)−0.0220 (11)−0.0203 (9)0.0224 (9)
N20.0407 (11)0.0357 (12)0.0388 (12)0.0002 (9)0.0007 (9)0.0048 (10)
C170.0574 (17)0.0432 (16)0.0460 (17)0.0028 (13)−0.0073 (13)0.0088 (13)
C80.0411 (13)0.0378 (15)0.0342 (13)0.0026 (11)0.0065 (11)−0.0002 (11)
C140.0407 (13)0.0374 (14)0.0390 (15)0.0019 (11)−0.0008 (11)0.0004 (12)
C100.0366 (12)0.0439 (15)0.0358 (14)0.0035 (11)0.0004 (10)0.0011 (12)
C90.0402 (13)0.0401 (15)0.0412 (14)0.0019 (11)0.0003 (11)0.0005 (12)
C200.084 (2)0.0478 (18)0.0534 (19)0.0053 (17)−0.0091 (17)0.0070 (16)
C180.093 (2)0.0577 (19)0.0371 (16)0.0218 (18)0.0102 (16)0.0069 (15)
C160.0633 (18)0.064 (2)0.0510 (18)0.0255 (16)0.0034 (14)0.0056 (15)
C150.0631 (18)0.065 (2)0.0383 (15)0.0189 (16)0.0066 (13)0.0074 (14)
C20.0499 (16)0.0527 (19)0.0617 (19)−0.0188 (14)−0.0007 (14)0.0050 (15)
C50.0418 (14)0.0539 (18)0.0522 (16)−0.0050 (13)−0.0060 (13)−0.0024 (14)
C190.078 (2)0.0560 (19)0.0410 (16)0.0208 (16)0.0178 (15)0.0044 (14)
C40.068 (2)0.0479 (18)0.072 (2)−0.0081 (16)0.0016 (17)0.0148 (16)
C10.0425 (14)0.0533 (18)0.0489 (16)−0.0033 (13)−0.0048 (12)0.0027 (14)
C70.0492 (15)0.0412 (16)0.0626 (19)−0.0040 (13)−0.0011 (14)−0.0014 (14)
C60.0496 (16)0.0511 (19)0.075 (2)−0.0158 (14)−0.0031 (15)−0.0054 (16)
C30.0501 (15)0.0439 (16)0.0444 (16)−0.0074 (13)0.0052 (12)0.0043 (13)
B10.0478 (17)0.0419 (18)0.0421 (17)0.0003 (14)−0.0056 (14)0.0069 (15)
C110.079 (2)0.0441 (19)0.112 (3)−0.0110 (17)−0.013 (2)0.0184 (19)
C130.0506 (17)0.078 (2)0.086 (2)−0.0111 (16)−0.0224 (17)0.0132 (19)
C120.0591 (19)0.077 (2)0.086 (2)−0.0084 (18)−0.0288 (18)0.0025 (19)
N30.111 (2)0.0673 (19)0.0713 (19)0.0198 (18)−0.0186 (17)0.0168 (16)
F2—B11.382 (4)C2—C11.374 (4)
N1—C51.350 (3)C2—C31.394 (4)
N1—C91.400 (3)C2—H20.9300
N1—B11.535 (4)C5—C61.390 (4)
F1—B11.384 (3)C5—C121.494 (4)
N2—C31.346 (3)C19—H190.9300
N2—C101.408 (3)C4—C31.482 (4)
N2—B11.545 (4)C4—H4A0.9600
C17—C181.376 (4)C4—H4B0.9600
C17—C161.378 (4)C4—H4C0.9600
C17—C201.440 (4)C1—C131.504 (4)
C8—C101.390 (3)C7—C61.373 (4)
C8—C91.398 (3)C7—C111.500 (4)
C8—C141.483 (3)C6—H30.9300
C14—C191.378 (4)C11—H5A0.9600
C14—C151.382 (4)C11—H5B0.9600
C10—C11.429 (4)C11—H5C0.9600
C9—C71.426 (4)C13—H13A0.9600
C20—N31.138 (4)C13—H13B0.9600
C18—C191.371 (4)C13—H13C0.9600
C18—H180.9300C12—H1A0.9600
C16—C151.384 (4)C12—H1B0.9600
C16—H160.9300C12—H1C0.9600
C15—H150.9300
C5—N1—C9107.8 (2)C3—C4—H4B109.5
C5—N1—B1126.7 (2)H4A—C4—H4B109.5
C9—N1—B1125.5 (2)C3—C4—H4C109.5
C3—N2—C10108.5 (2)H4A—C4—H4C109.5
C3—N2—B1126.5 (2)H4B—C4—H4C109.5
C10—N2—B1125.0 (2)C2—C1—C10106.4 (2)
C18—C17—C16119.6 (2)C2—C1—C13124.7 (3)
C18—C17—C20119.5 (3)C10—C1—C13128.8 (3)
C16—C17—C20120.9 (3)C6—C7—C9105.7 (2)
C10—C8—C9121.5 (2)C6—C7—C11125.2 (3)
C10—C8—C14119.2 (2)C9—C7—C11129.1 (3)
C9—C8—C14119.2 (2)C7—C6—C5109.5 (2)
C19—C14—C15118.5 (2)C7—C6—H3125.3
C19—C14—C8119.6 (2)C5—C6—H3125.3
C15—C14—C8121.9 (2)N2—C3—C2108.9 (2)
C8—C10—N2120.2 (2)N2—C3—C4123.1 (3)
C8—C10—C1132.8 (2)C2—C3—C4127.9 (3)
N2—C10—C1107.0 (2)F2—B1—F1109.1 (2)
C8—C9—N1120.2 (2)F2—B1—N1110.6 (2)
C8—C9—C7131.7 (2)F1—B1—N1109.9 (2)
N1—C9—C7108.0 (2)F2—B1—N2109.5 (2)
N3—C20—C17177.9 (4)F1—B1—N2110.3 (2)
C19—C18—C17120.1 (3)N1—B1—N2107.3 (2)
C19—C18—H18119.9C7—C11—H5A109.5
C17—C18—H18119.9C7—C11—H5B109.5
C17—C16—C15119.9 (3)H5A—C11—H5B109.5
C17—C16—H16120.1C7—C11—H5C109.5
C15—C16—H16120.1H5A—C11—H5C109.5
C14—C15—C16120.7 (3)H5B—C11—H5C109.5
C14—C15—H15119.7C1—C13—H13A109.5
C16—C15—H15119.7C1—C13—H13B109.5
C1—C2—C3109.1 (2)H13A—C13—H13B109.5
C1—C2—H2125.4C1—C13—H13C109.5
C3—C2—H2125.4H13A—C13—H13C109.5
N1—C5—C6109.0 (2)H13B—C13—H13C109.5
N1—C5—C12123.0 (3)C5—C12—H1A109.5
C6—C5—C12128.0 (3)C5—C12—H1B109.5
C18—C19—C14121.1 (3)H1A—C12—H1B109.5
C18—C19—H19119.4C5—C12—H1C109.5
C14—C19—H19119.4H1A—C12—H1C109.5
C3—C4—H4A109.5H1B—C12—H1C109.5
Table 1

Selected bond lengths (Å)

F2—B11.382 (4)
N1—C51.350 (3)
N1—C91.400 (3)
N1—B11.535 (4)
F1—B11.384 (3)
N2—C31.346 (3)
N2—C101.408 (3)
N2—B11.545 (4)
C8—C101.390 (3)
C8—C91.398 (3)
C10—C11.429 (4)
C9—C71.426 (4)
  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Novel fluorescent dyes with fused perylene tetracarboxlic diimide and BODIPY analogue structures.

Authors:  Junqian Feng; Baolong Liang; Delou Wang; Lin Xue; Xiyou Li
Journal:  Org Lett       Date:  2008-09-18       Impact factor: 6.005

3.  BODIPY dyes and their derivatives: syntheses and spectroscopic properties.

Authors:  Aurore Loudet; Kevin Burgess
Journal:  Chem Rev       Date:  2007-10-09       Impact factor: 60.622

4.  Bis(BF2)-2,2'-bidipyrrins (BisBODIPYs): highly fluorescent BODIPY dimers with large stokes shifts.

Authors:  Martin Bröring; Robin Krüger; Stephan Link; Christian Kleeberg; Silke Köhler; Xiulian Xie; Barbara Ventura; Lucia Flamigni
Journal:  Chemistry       Date:  2008       Impact factor: 5.236
  4 in total
  2 in total

1.  A BODIPY Based Fluorescent Probe for the Rapid Detection of Hypochlorite.

Authors:  Lusheng Wang; Bolin Li; Chao Jiang; Ruopei Sun; Peizhuo Hu; Suwen Chen; Wangsuo Wu
Journal:  J Fluoresc       Date:  2018-06-25       Impact factor: 2.217

2.  4,4-Difluoro-8-(4-iodo-phen-yl)-1,3,5,7-tetra-methyl-3a-aza-4a-azonia-4-borata-s-indacene.

Authors:  Yongling Sun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-04-04
  2 in total

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