12-Di-methyl-amino-2,2-di-fluoro-8-phenyl-1λ(5),3-di-aza-2λ(4)-boratri-cyclo-[7.3.0.0(3,7)]dodeca-1(12),4,6,8,10-pentaen-1-ylium.

In the title boron-dipyrromethene derivative, C17H16BF2N3, the benzene ring and the boron-dipyrromethene mean plane form a dihedral angle of 55.82 (8)°. In the crystal, pairs of C-H⋯F inter-actions link the mol-ecules, forming inversion dimers. Further C-H⋯F inter-actions link the dimers into a three-dimensional network.

Related literature

For the synthesis and applications of related 4,4-di­fluoro-4-bora-3a,4a-di­aza-s-indacene derivatives, see: Trieflinger et al. (2005 ▶). For related structures, see: Jiao et al. (2011 ▶).

Experimental

Crystal data

C17H16BF2N3

M = 311.14

Monoclinic,

a = 7.8033 (6) Å

b = 25.524 (2) Å

c = 9.9776 (5) Å

β = 128.671 (4)°

V = 1551.5 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.981

11054 measured reflections

2736 independent reflections

2025 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.119

S = 1.03

2736 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813010404/rk2400sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010404/rk2400Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010404/rk2400Isup3.cml

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

C17H16BF2N3	F(000) = 648
Mr = 311.14	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4251 reflections
a = 7.8033 (6) Å	θ = 2.7–24.3°
b = 25.524 (2) Å	µ = 0.10 mm−1
c = 9.9776 (5) Å	T = 295 K
β = 128.671 (4)°	Block, colourless
V = 1551.5 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2736 independent reflections
Radiation source: fine-focus sealed tube	2025 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.972, Tmax = 0.981	k = −30→30
11054 measured reflections	l = −11→11

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0582P)2 + 0.2638P] where P = (Fo2 + 2Fc2)/3
2736 reflections	(Δ/σ)max = 0.005
210 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.14 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.

	x	y	z	Uiso*/Ueq
F1	−0.28223 (17)	0.91338 (5)	0.54009 (14)	0.0842 (4)
F2	−0.0433 (2)	0.98113 (4)	0.67169 (16)	0.0884 (4)
N1	0.0902 (2)	0.90034 (6)	0.65707 (18)	0.0593 (4)
N2	−0.0100 (2)	0.91017 (5)	0.84906 (17)	0.0543 (4)
N3	−0.2640 (3)	0.95619 (7)	0.8700 (2)	0.0779 (5)
C1	0.1083 (4)	0.91003 (9)	0.5324 (3)	0.0760 (6)
H1	0.0217	0.9335	0.4423	0.091*
C2	0.2720 (4)	0.88033 (10)	0.5591 (3)	0.0821 (6)
H2	0.3155	0.8798	0.4910	0.098*
C3	0.3621 (3)	0.85096 (8)	0.7062 (2)	0.0685 (5)
H3	0.4772	0.8272	0.7554	0.082*
C4	0.2477 (3)	0.86380 (7)	0.7662 (2)	0.0552 (4)
C5	0.2796 (3)	0.84981 (6)	0.9186 (2)	0.0510 (4)
C6	0.4562 (3)	0.81223 (7)	1.0379 (2)	0.0563 (4)
C7	0.4630 (4)	0.76322 (7)	0.9807 (3)	0.0757 (6)
H7	0.3519	0.7533	0.8678	0.091*
C8	0.6331 (5)	0.72935 (9)	1.0903 (4)	0.0968 (8)
H8	0.6366	0.6966	1.0513	0.116*
C9	0.7971 (5)	0.74379 (12)	1.2564 (4)	0.1039 (9)
H9	0.9126	0.7209	1.3295	0.125*
C10	0.7929 (4)	0.79204 (11)	1.3165 (3)	0.0923 (7)
H10	0.9040	0.8015	1.4300	0.111*
C11	0.6232 (3)	0.82612 (8)	1.2073 (2)	0.0696 (5)
H11	0.6203	0.8587	1.2474	0.084*
C12	0.1544 (3)	0.87210 (6)	0.9555 (2)	0.0512 (4)
C13	0.1508 (3)	0.86084 (7)	1.0927 (2)	0.0629 (5)
H13	0.2419	0.8372	1.1811	0.075*
C14	−0.0056 (3)	0.88989 (8)	1.0739 (3)	0.0705 (5)
H14	−0.0427	0.8897	1.1462	0.085*
C15	−0.1061 (3)	0.92141 (7)	0.9228 (2)	0.0621 (5)
C16	−0.3699 (4)	0.99063 (10)	0.7212 (4)	0.1032 (8)
H16A	−0.2601	1.0099	0.7266	0.155*
H16B	−0.4650	1.0146	0.7208	0.155*
H16C	−0.4545	0.9700	0.6181	0.155*
C17	−0.3488 (4)	0.96200 (12)	0.9644 (3)	0.1063 (9)
H17A	−0.3107	0.9317	1.0349	0.159*
H17B	−0.5057	0.9655	0.8847	0.159*
H17C	−0.2860	0.9926	1.0356	0.159*
B1	−0.0669 (3)	0.92741 (8)	0.6751 (3)	0.0601 (5)

	U11	U22	U33	U12	U13	U23
F1	0.0555 (6)	0.1025 (9)	0.0600 (7)	0.0046 (6)	0.0193 (6)	−0.0029 (6)
F2	0.1155 (10)	0.0568 (7)	0.0922 (9)	0.0042 (6)	0.0646 (8)	0.0128 (6)
N1	0.0582 (8)	0.0667 (9)	0.0467 (8)	−0.0010 (7)	0.0297 (7)	0.0060 (7)
N2	0.0504 (8)	0.0549 (8)	0.0527 (8)	0.0015 (6)	0.0299 (7)	−0.0012 (6)
N3	0.0586 (9)	0.0861 (12)	0.0789 (12)	0.0042 (9)	0.0379 (9)	−0.0200 (9)
C1	0.0825 (14)	0.0895 (14)	0.0521 (11)	−0.0032 (12)	0.0402 (11)	0.0119 (10)
C2	0.0860 (15)	0.1096 (17)	0.0647 (13)	−0.0059 (13)	0.0539 (12)	0.0010 (12)
C3	0.0648 (11)	0.0866 (13)	0.0593 (11)	0.0004 (10)	0.0414 (10)	−0.0020 (10)
C4	0.0523 (9)	0.0622 (10)	0.0466 (9)	−0.0033 (8)	0.0287 (8)	−0.0012 (8)
C5	0.0501 (9)	0.0512 (9)	0.0462 (9)	−0.0036 (7)	0.0274 (8)	−0.0015 (7)
C6	0.0579 (10)	0.0579 (10)	0.0564 (11)	0.0046 (8)	0.0373 (9)	0.0069 (8)
C7	0.0912 (15)	0.0622 (11)	0.0837 (14)	0.0110 (11)	0.0595 (13)	0.0051 (10)
C8	0.122 (2)	0.0736 (14)	0.128 (2)	0.0338 (15)	0.094 (2)	0.0272 (15)
C9	0.0907 (18)	0.109 (2)	0.126 (2)	0.0468 (16)	0.0742 (19)	0.0593 (18)
C10	0.0657 (13)	0.1115 (19)	0.0761 (15)	0.0170 (13)	0.0327 (12)	0.0309 (14)
C11	0.0610 (11)	0.0743 (12)	0.0601 (12)	0.0052 (10)	0.0312 (10)	0.0095 (10)
C12	0.0515 (9)	0.0515 (9)	0.0472 (9)	−0.0021 (7)	0.0292 (8)	−0.0016 (7)
C13	0.0655 (11)	0.0714 (11)	0.0520 (10)	−0.0016 (9)	0.0368 (9)	0.0004 (9)
C14	0.0677 (12)	0.0925 (14)	0.0606 (12)	−0.0045 (11)	0.0446 (10)	−0.0108 (10)
C15	0.0522 (10)	0.0667 (11)	0.0604 (11)	−0.0061 (9)	0.0317 (9)	−0.0164 (9)
C16	0.0863 (16)	0.0873 (16)	0.119 (2)	0.0278 (14)	0.0557 (16)	0.0073 (15)
C17	0.0768 (15)	0.141 (2)	0.1026 (19)	0.0081 (15)	0.0569 (15)	−0.0398 (16)
B1	0.0562 (12)	0.0545 (11)	0.0519 (12)	−0.0006 (9)	0.0253 (10)	0.0022 (9)

F1—B1	1.392 (2)	C6—C7	1.390 (3)
F2—B1	1.387 (2)	C7—C8	1.375 (3)
N1—C1	1.359 (2)	C7—H7	0.9300
N1—C4	1.376 (2)	C8—C9	1.368 (4)
N1—B1	1.513 (3)	C8—H8	0.9300
N2—C15	1.369 (2)	C9—C10	1.379 (4)
N2—C12	1.420 (2)	C9—H9	0.9300
N2—B1	1.562 (3)	C10—C11	1.376 (3)
N3—C15	1.331 (2)	C10—H10	0.9300
N3—C17	1.458 (3)	C11—H11	0.9300
N3—C16	1.458 (3)	C12—C13	1.416 (2)
C1—C2	1.361 (3)	C13—C14	1.337 (3)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.386 (3)	C14—C15	1.435 (3)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.388 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.425 (2)	C16—H16C	0.9600
C5—C12	1.365 (2)	C17—H17A	0.9600
C5—C6	1.479 (2)	C17—H17B	0.9600
C6—C11	1.389 (3)	C17—H17C	0.9600
C1—N1—C4	107.13 (16)	C11—C10—C9	119.5 (2)
C1—N1—B1	125.53 (16)	C11—C10—H10	120.2
C4—N1—B1	127.26 (14)	C9—C10—H10	120.2
C15—N2—C12	106.50 (14)	C10—C11—C6	120.6 (2)
C15—N2—B1	131.83 (15)	C10—C11—H11	119.7
C12—N2—B1	121.37 (14)	C6—C11—H11	119.7
C15—N3—C17	119.6 (2)	C5—C12—C13	128.79 (16)
C15—N3—C16	126.89 (19)	C5—C12—N2	123.22 (15)
C17—N3—C16	113.53 (19)	C13—C12—N2	107.89 (15)
N1—C1—C2	109.95 (18)	C14—C13—C12	108.66 (17)
N1—C1—H1	125.0	C14—C13—H13	125.7
C2—C1—H1	125.0	C12—C13—H13	125.7
C1—C2—C3	107.53 (18)	C13—C14—C15	108.04 (17)
C1—C2—H2	126.2	C13—C14—H14	126.0
C3—C2—H2	126.2	C15—C14—H14	126.0
C2—C3—C4	106.95 (19)	N3—C15—N2	127.54 (18)
C2—C3—H3	126.5	N3—C15—C14	123.55 (18)
C4—C3—H3	126.5	N2—C15—C14	108.89 (16)
N1—C4—C3	108.44 (16)	N3—C16—H16A	109.5
N1—C4—C5	119.19 (15)	N3—C16—H16B	109.5
C3—C4—C5	132.08 (17)	H16A—C16—H16B	109.5
C12—C5—C4	120.46 (15)	N3—C16—H16C	109.5
C12—C5—C6	121.14 (15)	H16A—C16—H16C	109.5
C4—C5—C6	118.36 (15)	H16B—C16—H16C	109.5
C11—C6—C7	118.84 (18)	N3—C17—H17A	109.5
C11—C6—C5	120.53 (16)	N3—C17—H17B	109.5
C7—C6—C5	120.58 (17)	H17A—C17—H17B	109.5
C8—C7—C6	120.3 (2)	N3—C17—H17C	109.5
C8—C7—H7	119.8	H17A—C17—H17C	109.5
C6—C7—H7	119.8	H17B—C17—H17C	109.5
C9—C8—C7	120.1 (2)	F2—B1—F1	109.21 (15)
C9—C8—H8	119.9	F2—B1—N1	108.58 (16)
C7—C8—H8	119.9	F1—B1—N1	110.18 (16)
C8—C9—C10	120.6 (2)	F2—B1—N2	110.87 (15)
C8—C9—H9	119.7	F1—B1—N2	109.63 (16)
C10—C9—H9	119.7	N1—B1—N2	108.35 (14)
C4—N1—C1—C2	0.4 (2)	C15—N2—C12—C5	177.30 (15)
B1—N1—C1—C2	177.39 (18)	B1—N2—C12—C5	2.9 (2)
N1—C1—C2—C3	−0.4 (3)	C15—N2—C12—C13	0.65 (18)
C1—C2—C3—C4	0.2 (2)	B1—N2—C12—C13	−173.74 (15)
C1—N1—C4—C3	−0.3 (2)	C5—C12—C13—C14	−176.43 (17)
B1—N1—C4—C3	−177.21 (16)	N2—C12—C13—C14	0.0 (2)
C1—N1—C4—C5	174.28 (16)	C12—C13—C14—C15	−0.6 (2)
B1—N1—C4—C5	−2.6 (3)	C17—N3—C15—N2	178.89 (18)
C2—C3—C4—N1	0.1 (2)	C16—N3—C15—N2	−0.4 (3)
C2—C3—C4—C5	−173.55 (19)	C17—N3—C15—C14	−2.5 (3)
N1—C4—C5—C12	0.4 (2)	C16—N3—C15—C14	178.2 (2)
C3—C4—C5—C12	173.53 (18)	C12—N2—C15—N3	177.73 (17)
N1—C4—C5—C6	−177.34 (15)	B1—N2—C15—N3	−8.7 (3)
C3—C4—C5—C6	−4.2 (3)	C12—N2—C15—C14	−1.01 (18)
C12—C5—C6—C11	−56.0 (2)	B1—N2—C15—C14	172.56 (17)
C4—C5—C6—C11	121.79 (18)	C13—C14—C15—N3	−177.78 (17)
C12—C5—C6—C7	126.68 (19)	C13—C14—C15—N2	1.0 (2)
C4—C5—C6—C7	−55.6 (2)	C1—N1—B1—F2	−51.6 (2)
C11—C6—C7—C8	−0.4 (3)	C4—N1—B1—F2	124.74 (18)
C5—C6—C7—C8	177.02 (19)	C1—N1—B1—F1	68.0 (2)
C6—C7—C8—C9	−0.1 (4)	C4—N1—B1—F1	−115.69 (19)
C7—C8—C9—C10	0.7 (4)	C1—N1—B1—N2	−172.08 (16)
C8—C9—C10—C11	−0.8 (4)	C4—N1—B1—N2	4.2 (2)
C9—C10—C11—C6	0.3 (3)	C15—N2—B1—F2	63.9 (2)
C7—C6—C11—C10	0.3 (3)	C12—N2—B1—F2	−123.27 (17)
C5—C6—C11—C10	−177.12 (18)	C15—N2—B1—F1	−56.7 (2)
C4—C5—C12—C13	175.20 (16)	C12—N2—B1—F1	116.07 (17)
C6—C5—C12—C13	−7.1 (3)	C15—N2—B1—N1	−176.99 (16)
C4—C5—C12—N2	−0.7 (2)	C12—N2—B1—N1	−4.2 (2)
C6—C5—C12—N2	176.99 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F2i	0.93	2.51	3.291 (3)	142
C17—H17C···F2ii	0.96	2.49	3.282 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯F2i	0.93	2.51	3.291 (3)	142
C17—H17C⋯F2ii	0.96	2.49	3.282 (3)	140

Symmetry codes: (i) ; (ii) .