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

In the title compound, C(13)H(15)BF(2)N(2), the two pyrrole rings are almost coplanar, with a dihedral angle of 3.08 (10)°. The BF(2) plane is almost perpendicular to the boron-dipyrromethene ring plane, with a dihedral angle of 89.99 (7)°.

Related literature

For related literature, see: Bergström et al. (2002 ▶); Kollmannsberger et al. (1998 ▶); Kuhn et al. (1990 ▶); Trieflinger et al. (2005 ▶).

Experimental

Crystal data

C13H15BF2N2

M = 248.08

Monoclinic,

a = 7.6909 (8) Å

b = 14.3392 (15) Å

c = 11.8334 (10) Å

β = 111.108 (5)°

V = 1217.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.961, T max = 0.974

6540 measured reflections

2396 independent reflections

1963 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.126

S = 1.06

2396 reflections

167 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.24 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/S1600536808024057/at2574sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024057/at2574Isup2.hkl

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

C13H15B1F2N2	F000 = 520
Mr = 248.08	Dx = 1.353 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2682 reflections
a = 7.6909 (8) Å	θ = 2.8–27.9º
b = 14.3392 (15) Å	µ = 0.10 mm−1
c = 11.8334 (10) Å	T = 293 (2) K
β = 111.108 (5)º	Block, red
V = 1217.4 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Rigaku Mercury2 diffractometer	2396 independent reflections
Radiation source: fine-focus sealed tube	1963 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.019
Detector resolution: 13.6612 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 2.3º
φ and ω scans	h = −8→9
Absorption correction: empirical (using intensity measurements)(CrystalClear; Rigaku, 2005)	k = −17→16
Tmin = 0.961, Tmax = 0.974	l = −14→12
6540 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0669P)2 + 0.3386P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.007
2396 reflections	Δρmax = 0.27 e Å−3
167 parameters	Δρmin = −0.24 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
F1	0.90473 (14)	−0.13462 (7)	0.77523 (9)	0.0416 (3)
F2	0.59217 (14)	−0.11875 (7)	0.68465 (9)	0.0429 (3)
N1	0.77362 (17)	0.01985 (9)	0.76358 (11)	0.0296 (3)
N2	0.72797 (18)	−0.10054 (9)	0.90212 (12)	0.0302 (3)
C1	0.7917 (2)	0.06479 (12)	0.66762 (15)	0.0333 (4)
C2	0.8203 (2)	0.15979 (12)	0.69475 (16)	0.0368 (4)
H2A	0.8371	0.2054	0.6438	0.044*
C3	0.8194 (2)	0.17455 (11)	0.80964 (15)	0.0331 (4)
C4	0.7899 (2)	0.08638 (11)	0.85312 (14)	0.0296 (4)
C5	0.7747 (2)	0.06086 (11)	0.96176 (14)	0.0292 (4)
H5A	0.7865	0.1065	1.0199	0.035*
C6	0.7427 (2)	−0.03013 (11)	0.98692 (14)	0.0296 (4)
C7	0.7146 (2)	−0.06999 (12)	1.08848 (15)	0.0331 (4)
C8	0.6836 (2)	−0.16395 (12)	1.06306 (16)	0.0377 (4)
H8A	0.6607	−0.2083	1.1133	0.045*
C9	0.6926 (2)	−0.18101 (11)	0.94874 (15)	0.0343 (4)
C10	0.7815 (3)	0.01588 (13)	0.55463 (16)	0.0419 (4)
H10A	0.8497	−0.0416	0.5749	0.063*
H10B	0.8346	0.0547	0.5093	0.063*
H10C	0.6536	0.0030	0.5067	0.063*
C11	0.8416 (3)	0.26491 (12)	0.87641 (17)	0.0411 (4)
H11A	0.9168	0.3066	0.8498	0.062*
H11B	0.9011	0.2539	0.9618	0.062*
H11C	0.7213	0.2923	0.8606	0.062*
C12	0.7199 (2)	−0.01832 (13)	1.19915 (16)	0.0388 (4)
H12A	0.6385	−0.0482	1.2334	0.058*
H12B	0.6797	0.0448	1.1779	0.058*
H12C	0.8449	−0.0183	1.2574	0.058*
C13	0.6716 (3)	−0.27203 (12)	0.88435 (17)	0.0426 (4)
H13A	0.7826	−0.2851	0.8680	0.064*
H13B	0.5669	−0.2690	0.8094	0.064*
H13C	0.6516	−0.3206	0.9342	0.064*
B1	0.7490 (2)	−0.08597 (13)	0.77801 (16)	0.0310 (4)

	U11	U22	U33	U12	U13	U23
F1	0.0484 (6)	0.0363 (6)	0.0467 (6)	0.0106 (4)	0.0251 (5)	−0.0002 (4)
F2	0.0463 (6)	0.0438 (6)	0.0326 (6)	−0.0101 (4)	0.0070 (5)	−0.0031 (4)
N1	0.0304 (7)	0.0317 (7)	0.0272 (7)	0.0027 (5)	0.0109 (6)	0.0002 (5)
N2	0.0303 (7)	0.0297 (7)	0.0298 (7)	0.0031 (5)	0.0099 (6)	0.0009 (5)
C1	0.0331 (8)	0.0369 (9)	0.0312 (9)	0.0055 (7)	0.0132 (7)	0.0039 (7)
C2	0.0432 (9)	0.0346 (9)	0.0366 (9)	0.0045 (7)	0.0192 (8)	0.0060 (7)
C3	0.0321 (8)	0.0319 (8)	0.0371 (9)	0.0031 (6)	0.0145 (7)	0.0018 (7)
C4	0.0271 (8)	0.0311 (8)	0.0299 (8)	0.0035 (6)	0.0093 (6)	−0.0009 (6)
C5	0.0257 (7)	0.0311 (8)	0.0301 (8)	0.0031 (6)	0.0094 (6)	−0.0023 (6)
C6	0.0270 (7)	0.0337 (8)	0.0278 (8)	0.0046 (6)	0.0095 (6)	−0.0005 (6)
C7	0.0296 (8)	0.0383 (9)	0.0312 (9)	0.0046 (7)	0.0108 (7)	0.0036 (7)
C8	0.0418 (9)	0.0367 (9)	0.0364 (9)	0.0023 (7)	0.0163 (8)	0.0081 (7)
C9	0.0343 (9)	0.0325 (9)	0.0346 (9)	0.0023 (6)	0.0104 (7)	0.0030 (7)
C10	0.0510 (11)	0.0448 (10)	0.0336 (9)	0.0035 (8)	0.0197 (8)	−0.0003 (7)
C11	0.0495 (10)	0.0319 (9)	0.0447 (10)	−0.0003 (8)	0.0204 (9)	−0.0010 (7)
C12	0.0411 (9)	0.0460 (10)	0.0318 (9)	0.0039 (8)	0.0163 (8)	0.0005 (7)
C13	0.0511 (11)	0.0327 (9)	0.0421 (10)	−0.0013 (8)	0.0146 (8)	0.0008 (7)
B1	0.0326 (9)	0.0312 (9)	0.0287 (9)	0.0011 (7)	0.0105 (7)	−0.0004 (7)

F1—B1	1.397 (2)	C7—C8	1.382 (2)
F2—B1	1.392 (2)	C7—C12	1.492 (2)
N1—C1	1.356 (2)	C8—C9	1.401 (2)
N1—C4	1.3974 (19)	C8—H8A	0.9300
N1—B1	1.546 (2)	C9—C13	1.490 (2)
N2—C9	1.348 (2)	C10—H10A	0.9600
N2—C6	1.399 (2)	C10—H10B	0.9600
N2—B1	1.548 (2)	C10—H10C	0.9600
C1—C2	1.399 (2)	C11—H11A	0.9600
C1—C10	1.487 (2)	C11—H11B	0.9600
C2—C3	1.378 (2)	C11—H11C	0.9600
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.414 (2)	C12—H12B	0.9600
C3—C11	1.495 (2)	C12—H12C	0.9600
C4—C5	1.382 (2)	C13—H13A	0.9600
C5—C6	1.380 (2)	C13—H13B	0.9600
C5—H5A	0.9300	C13—H13C	0.9600
C6—C7	1.416 (2)
C1—N1—C4	107.60 (14)	C8—C9—C13	127.78 (15)
C1—N1—B1	127.78 (14)	C1—C10—H10A	109.5
C4—N1—B1	124.57 (13)	C1—C10—H10B	109.5
C9—N2—C6	107.47 (13)	H10A—C10—H10B	109.5
C9—N2—B1	127.51 (13)	C1—C10—H10C	109.5
C6—N2—B1	125.02 (13)	H10A—C10—H10C	109.5
N1—C1—C2	109.00 (14)	H10B—C10—H10C	109.5
N1—C1—C10	122.75 (15)	C3—C11—H11A	109.5
C2—C1—C10	128.25 (15)	C3—C11—H11B	109.5
C3—C2—C1	108.66 (14)	H11A—C11—H11B	109.5
C3—C2—H2A	125.7	C3—C11—H11C	109.5
C1—C2—H2A	125.7	H11A—C11—H11C	109.5
C2—C3—C4	106.26 (14)	H11B—C11—H11C	109.5
C2—C3—C11	127.90 (15)	C7—C12—H12A	109.5
C4—C3—C11	125.84 (15)	C7—C12—H12B	109.5
C5—C4—N1	120.68 (14)	H12A—C12—H12B	109.5
C5—C4—C3	130.84 (15)	C7—C12—H12C	109.5
N1—C4—C3	108.48 (14)	H12A—C12—H12C	109.5
C6—C5—C4	122.19 (14)	H12B—C12—H12C	109.5
C6—C5—H5A	118.9	C9—C13—H13A	109.5
C4—C5—H5A	118.9	C9—C13—H13B	109.5
C5—C6—N2	120.14 (14)	H13A—C13—H13B	109.5
C5—C6—C7	131.18 (15)	C9—C13—H13C	109.5
N2—C6—C7	108.66 (14)	H13A—C13—H13C	109.5
C8—C7—C6	106.01 (14)	H13B—C13—H13C	109.5
C8—C7—C12	128.52 (15)	F2—B1—F1	108.55 (14)
C6—C7—C12	125.47 (16)	F2—B1—N1	110.45 (13)
C7—C8—C9	108.40 (15)	F1—B1—N1	110.32 (13)
C7—C8—H8A	125.8	F2—B1—N2	110.53 (13)
C9—C8—H8A	125.8	F1—B1—N2	109.77 (13)
N2—C9—C8	109.46 (14)	N1—B1—N2	107.21 (13)
N2—C9—C13	122.76 (15)