4,4-Difluoro-1,3,5,7-tetra-methyl-8-penta-fluoro-phenyl-4-bora-3a,4a-diaza-s-indacene.

In the title dye compound, C(19)H(14)BF(7)N(2), the boron-dipyrromethene core lies on a crystallographic mirror plane which bis-ects the BF(2) and penta-fluoro-phenyl groups. The dihedral angle between the penta-fluoro-phenyl ring and the tricyclic system is thus 90° by symmetry. The sp(3)-hybridized B atom has a slightly distorted tetra-hedral coordination.

Related literature

For boron–dipyrromethene (BODIPY) dyes, see: Bergström et al. (2002 ▶); Trieflinger et al. (2005 ▶). For geometrical parameters in other BODIPY-based compounds, see: Picou et al.(1990 ▶); Wang et al.(2007 ▶); Kuhn et al. (1990 ▶).

Experimental

Crystal data

C19H14BF7N2

M = 414.13

Monoclinic,

a = 12.4060 (5) Å

b = 7.5490 (9) Å

c = 19.720 (3) Å

β = 97.12 (2)°

V = 1832.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.973, T max = 0.979

8232 measured reflections

1936 independent reflections

1585 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.162

S = 1.06

1936 reflections

170 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003703/bh2269sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003703/bh2269Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H14BF7N2	F(000) = 840
Mr = 414.13	Dx = 1.501 Mg m−3
Monoclinic, C2/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2y	Cell parameters from 2191 reflections
a = 12.4060 (5) Å	θ = 3.1–27.5°
b = 7.5490 (9) Å	µ = 0.14 mm−1
c = 19.720 (3) Å	T = 293 K
β = 97.12 (2)°	Prism, red
V = 1832.6 (4) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Rigaku SCXmini diffractometer	1936 independent reflections
Radiation source: fine-focus sealed tube	1585 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0°, θmin = 3.1°
ω scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.973, Tmax = 0.979	l = −24→24
8232 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.091P)2 + 0.8854P] where P = (Fo2 + 2Fc2)/3
1936 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.23 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
F1	0.12945 (15)	0.3502 (3)	0.07469 (8)	0.1040 (7)
F3	0.28302 (13)	0.18847 (16)	0.34101 (7)	0.0721 (5)
F4	0.35839 (14)	0.1888 (2)	0.47541 (8)	0.0928 (6)
F5	0.39356 (18)	0.5000	0.54333 (9)	0.0988 (9)
N1	0.08602 (19)	0.5000	0.17499 (11)	0.0486 (6)
N2	0.2747 (2)	0.5000	0.14360 (11)	0.0523 (6)
C1	−0.0234 (2)	0.5000	0.17144 (15)	0.0564 (7)
C2	−0.0523 (2)	0.5000	0.23784 (16)	0.0597 (8)
H2A	−0.1229	0.5000	0.2490	0.104 (14)*
C3	0.0406 (2)	0.5000	0.28399 (14)	0.0489 (7)
C4	0.1291 (2)	0.5000	0.24405 (12)	0.0446 (6)
C5	0.2418 (2)	0.5000	0.26194 (12)	0.0422 (6)
C6	0.3151 (2)	0.5000	0.21363 (13)	0.0475 (6)
C7	0.4316 (2)	0.5000	0.21939 (16)	0.0563 (7)
C8	0.4565 (3)	0.5000	0.15330 (17)	0.0682 (9)
H8A	0.5263	0.5000	0.1408	0.080 (11)*
C9	0.3606 (3)	0.5000	0.10769 (15)	0.0627 (8)
C10	−0.0981 (3)	0.5000	0.10532 (18)	0.0783 (11)
H10A	−0.0559	0.5000	0.0677	0.16 (2)*
H10B	−0.1430	0.6038	0.1031	0.23 (3)*
C11	0.0428 (3)	0.5000	0.36050 (15)	0.0629 (9)
H11A	−0.0302	0.5000	0.3719	0.079 (11)*
H11B	0.0801	0.6038	0.3792	0.093 (9)*
C12	0.3492 (4)	0.5000	0.03121 (18)	0.0875 (13)
H12A	0.2735	0.5000	0.0135	0.25 (4)*
H12B	0.3833	0.3962	0.0156	0.172 (19)*
C13	0.5127 (3)	0.5000	0.28225 (19)	0.0693 (9)
H13A	0.5847	0.5000	0.2693	0.126 (17)*
H13B	0.5027	0.3962	0.3089	0.129 (13)*
C14	0.2846 (2)	0.5000	0.33641 (13)	0.0425 (6)
C15	0.30342 (16)	0.3443 (3)	0.37278 (10)	0.0490 (5)
C16	0.34105 (17)	0.3429 (3)	0.44160 (11)	0.0602 (6)
C17	0.3592 (2)	0.5000	0.47584 (15)	0.0638 (9)
B1	0.1532 (3)	0.5000	0.11399 (17)	0.0612 (9)

	U11	U22	U33	U12	U13	U23
F1	0.0923 (11)	0.1505 (17)	0.0710 (10)	−0.0214 (11)	0.0177 (8)	−0.0597 (10)
F3	0.0976 (11)	0.0457 (7)	0.0730 (9)	0.0076 (7)	0.0110 (7)	0.0018 (6)
F4	0.1028 (12)	0.1033 (12)	0.0732 (10)	0.0309 (10)	0.0147 (8)	0.0448 (9)
F5	0.0785 (14)	0.177 (3)	0.0379 (10)	0.000	−0.0059 (9)	0.000
N1	0.0560 (13)	0.0546 (13)	0.0346 (11)	0.000	0.0027 (9)	0.000
N2	0.0601 (14)	0.0615 (14)	0.0377 (12)	0.000	0.0155 (10)	0.000
C1	0.0547 (17)	0.0633 (18)	0.0491 (16)	0.000	−0.0017 (12)	0.000
C2	0.0491 (16)	0.079 (2)	0.0516 (16)	0.000	0.0085 (13)	0.000
C3	0.0495 (15)	0.0576 (16)	0.0405 (14)	0.000	0.0086 (11)	0.000
C4	0.0520 (15)	0.0477 (14)	0.0337 (12)	0.000	0.0041 (10)	0.000
C5	0.0507 (14)	0.0386 (13)	0.0380 (13)	0.000	0.0081 (11)	0.000
C6	0.0535 (15)	0.0490 (15)	0.0408 (14)	0.000	0.0089 (11)	0.000
C7	0.0541 (16)	0.0601 (17)	0.0570 (17)	0.000	0.0157 (13)	0.000
C8	0.0590 (19)	0.087 (2)	0.064 (2)	0.000	0.0271 (16)	0.000
C9	0.075 (2)	0.071 (2)	0.0468 (16)	0.000	0.0246 (15)	0.000
C10	0.069 (2)	0.108 (3)	0.0514 (19)	0.000	−0.0157 (16)	0.000
C11	0.0517 (16)	0.095 (3)	0.0437 (15)	0.000	0.0130 (13)	0.000
C12	0.099 (3)	0.121 (4)	0.0486 (19)	0.000	0.033 (2)	0.000
C13	0.0507 (17)	0.088 (3)	0.069 (2)	0.000	0.0068 (15)	0.000
C14	0.0428 (13)	0.0479 (14)	0.0375 (13)	0.000	0.0077 (10)	0.000
C15	0.0507 (10)	0.0498 (11)	0.0474 (10)	0.0060 (9)	0.0099 (8)	0.0030 (8)
C16	0.0533 (11)	0.0795 (16)	0.0488 (11)	0.0128 (11)	0.0104 (9)	0.0208 (11)
C17	0.0490 (16)	0.104 (3)	0.0380 (14)	0.000	0.0051 (12)	0.000
B1	0.068 (2)	0.082 (2)	0.0346 (15)	0.000	0.0083 (14)	0.000

B1—F1	1.382 (3)	C7—C8	1.376 (4)
B1—N1	1.546 (4)	C7—C13	1.497 (5)
B1—N2	1.548 (5)	C8—C9	1.400 (5)
F3—C15	1.342 (3)	C8—H8A	0.9301
F4—C16	1.345 (3)	C9—C12	1.497 (4)
F5—C17	1.346 (3)	C10—H10A	0.9598
N1—C1	1.350 (4)	C10—H10B	0.9600
N1—C4	1.400 (3)	C11—H11A	0.9601
N2—C9	1.350 (4)	C11—H11B	0.9600
N2—C6	1.409 (4)	C12—H12A	0.9600
C1—C2	1.400 (4)	C12—H12B	0.9601
C1—C10	1.503 (4)	C13—H13A	0.9600
C2—C3	1.377 (4)	C13—H13B	0.9600
C2—H2A	0.9298	C14—C15	1.382 (2)
C3—C4	1.428 (4)	C14—C15i	1.382 (2)
C3—C11	1.506 (4)	C15—C16	1.379 (3)
C4—C5	1.398 (4)	C16—C17	1.370 (3)
C5—C6	1.397 (4)	C17—C16i	1.370 (3)
C5—C14	1.498 (3)	B1—F1i	1.382 (3)
C6—C7	1.435 (4)
C1—N1—C4	108.1 (2)	C8—C9—C12	127.9 (3)
C1—N1—B1	126.5 (2)	C1—C10—H10A	109.6
C4—N1—B1	125.4 (2)	C1—C10—H10B	109.4
C9—N2—C6	107.8 (3)	H10A—C10—H10B	109.5
C9—N2—B1	126.6 (3)	C3—C11—H11A	109.5
C6—N2—B1	125.5 (2)	C3—C11—H11B	109.5
N1—C1—C2	108.9 (3)	H11A—C11—H11B	109.5
N1—C1—C10	123.6 (3)	C9—C12—H12A	109.5
C2—C1—C10	127.6 (3)	C9—C12—H12B	109.5
C3—C2—C1	109.2 (3)	H12A—C12—H12B	109.5
C3—C2—H2A	125.5	C7—C13—H13A	109.4
C1—C2—H2A	125.4	C7—C13—H13B	109.5
C2—C3—C4	105.8 (2)	H13A—C13—H13B	109.5
C2—C3—C11	124.9 (3)	C15—C14—C15i	116.6 (2)
C4—C3—C11	129.2 (3)	C15—C14—C5	121.69 (13)
N1—C4—C5	119.6 (2)	C15i—C14—C5	121.69 (13)
N1—C4—C3	108.0 (2)	F3—C15—C14	119.56 (18)
C5—C4—C3	132.3 (2)	F3—C15—C16	118.27 (19)
C6—C5—C4	122.9 (2)	C14—C15—C16	122.2 (2)
C6—C5—C14	119.1 (2)	F4—C16—C17	119.9 (2)
C4—C5—C14	118.0 (2)	F4—C16—C15	120.6 (2)
C5—C6—N2	119.1 (2)	C17—C16—C15	119.5 (2)
C5—C6—C7	132.9 (3)	F5—C17—C16	119.99 (14)
N2—C6—C7	108.0 (2)	F5—C17—C16i	119.99 (14)
C8—C7—C6	105.5 (3)	C16—C17—C16i	120.0 (3)
C8—C7—C13	125.3 (3)	F1—B1—F1i	109.8 (3)
C6—C7—C13	129.2 (3)	N1—B1—N2	107.5 (2)
C7—C8—C9	109.6 (3)	F1—B1—N1	109.8 (2)
C7—C8—H8A	125.2	F1i—B1—N1	109.8 (2)
C9—C8—H8A	125.1	F1—B1—N2	110.0 (2)
N2—C9—C8	109.0 (3)	F1i—B1—N2	110.0 (2)
N2—C9—C12	123.1 (3)