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

In the title compound, C(19)H(18)BF(2)IN(2), which is a boron-dipyrromethene (BODIPY) derivative, the BODIPY mean plane forms dihedral angles of 88.95 (4) and 78.21 (3)° with the F/B/F and 4-iodo-phenyl planes, respectively.

Related literature

For the crystal structures of related boron–dipyrromethene derivatives, see: Zhou (2010 ▶); Chen & Jiang (2011 ▶); Hinkle et al. (2011 ▶); Cui et al. (2012 ▶).

Experimental

Crystal data

C19H18BF2IN2

M = 450.06

Monoclinic,

a = 12.1004 (3) Å

b = 8.1992 (2) Å

c = 18.0607 (4) Å

β = 90.577 (3)°

V = 1791.77 (8) Å3

Z = 4

Cu Kα radiation

μ = 14.24 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; Bruker, 2007 ▶) T min = 0.102, T max = 0.110

6829 measured reflections

3348 independent reflections

2770 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.166

S = 1.05

3348 reflections

230 parameters

H-atom parameters constrained

Δρmax = 1.33 e Å−3

Δρmin = −1.36 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812004072/cv5238sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812004072/cv5238Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812004072/cv5238Isup3.cml

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

C19H18BF2IN2	F(000) = 888
Mr = 450.06	Dx = 1.668 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.1004 (3) Å	Cell parameters from 3440 reflections
b = 8.1992 (2) Å	µ = 14.24 mm−1
c = 18.0607 (4) Å	T = 293 K
β = 90.577 (3)°	Block, red
V = 1791.77 (8) Å3	0.20 × 0.18 × 0.16 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3348 independent reflections
Radiation source: fine-focus sealed tube	2770 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
phi and ω scans	θmax = 70.8°, θmin = 4.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −9→14
Tmin = 0.102, Tmax = 0.110	k = −10→8
6829 measured reflections	l = −21→21

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0917P)2 + 0.3111P] where P = (Fo2 + 2Fc2)/3
3348 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 1.33 e Å−3
0 restraints	Δρmin = −1.36 e Å−3

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
I	0.46758 (4)	−0.22865 (6)	0.54374 (2)	0.0515 (2)
F1	1.0026 (3)	0.3904 (5)	0.8798 (2)	0.0540 (10)
N2	0.8395 (4)	0.2246 (6)	0.8934 (3)	0.0334 (11)
F2	0.8499 (4)	0.5070 (5)	0.9279 (2)	0.0569 (11)
N1	0.8479 (3)	0.4411 (6)	0.7983 (2)	0.0305 (10)
C15	0.7292 (4)	0.0148 (7)	0.6658 (3)	0.0345 (13)
H6	0.8056	0.0233	0.6619	0.041*
C2	0.8031 (5)	−0.0117 (8)	0.9496 (3)	0.0401 (14)
H7	0.8028	−0.0933	0.9853	0.048*
C9	0.7415 (4)	0.1937 (7)	0.7768 (3)	0.0278 (11)
C1	0.7510 (4)	−0.0199 (7)	0.8812 (3)	0.0332 (12)
C14	0.6760 (4)	0.0933 (7)	0.7238 (3)	0.0280 (11)
C10	0.7747 (4)	0.1305 (7)	0.8456 (3)	0.0272 (11)
C8	0.7754 (4)	0.3485 (7)	0.7541 (3)	0.0273 (11)
C7	0.7538 (4)	0.4399 (7)	0.6886 (3)	0.0325 (12)
C13	0.9491 (6)	0.7053 (9)	0.7908 (4)	0.0510 (17)
H15B	1.0239	0.6742	0.7807	0.077*
H15C	0.9397	0.7166	0.8432	0.077*
H15A	0.9331	0.8074	0.7669	0.077*
C6	0.8157 (5)	0.5794 (8)	0.6943 (3)	0.0390 (13)
H16	0.8192	0.6614	0.6588	0.047*
C4	0.9226 (6)	0.2003 (10)	1.0198 (4)	0.0522 (18)
H17C	0.8915	0.3008	1.0371	0.078*
H17A	0.9972	0.2187	1.0043	0.078*
H17B	0.9223	0.1214	1.0591	0.078*
C17	0.5569 (5)	−0.0896 (7)	0.6206 (3)	0.0357 (13)
C5	0.8727 (5)	0.5783 (8)	0.7620 (3)	0.0354 (13)
C18	0.5021 (5)	−0.0124 (8)	0.6784 (3)	0.0370 (13)
H20	0.4259	−0.0218	0.6826	0.044*
C16	0.6705 (5)	−0.0756 (8)	0.6139 (3)	0.0389 (14)
H21	0.7069	−0.1262	0.5750	0.047*
C19	0.5624 (5)	0.0783 (8)	0.7293 (3)	0.0362 (13)
H22	0.5260	0.1299	0.7679	0.043*
C3	0.8559 (5)	0.1382 (8)	0.9563 (3)	0.0384 (14)
B	0.8873 (5)	0.3956 (9)	0.8772 (4)	0.0346 (14)
C12	0.6745 (5)	0.4019 (9)	0.6266 (3)	0.0465 (16)
H25A	0.6999	0.3077	0.6002	0.070*
H25C	0.6703	0.4933	0.5935	0.070*
H25B	0.6027	0.3804	0.6465	0.070*
C11A	0.6824 (5)	−0.1606 (8)	0.8552 (4)	0.0419 (14)
H1AB	0.6056	−0.1314	0.8567	0.063*
H1AC	0.6955	−0.2529	0.8868	0.063*
H1AA	0.7020	−0.1878	0.8053	0.063*

	U11	U22	U33	U12	U13	U23
I	0.0601 (4)	0.0609 (4)	0.0331 (3)	−0.0223 (2)	−0.0201 (2)	−0.00197 (17)
F1	0.0302 (17)	0.081 (3)	0.050 (2)	−0.0144 (19)	−0.0154 (16)	0.009 (2)
N2	0.031 (2)	0.048 (3)	0.021 (2)	0.001 (2)	−0.0043 (19)	−0.003 (2)
F2	0.082 (3)	0.057 (2)	0.0314 (18)	−0.001 (2)	−0.0013 (19)	−0.0118 (17)
N1	0.025 (2)	0.039 (3)	0.027 (2)	−0.001 (2)	−0.0030 (17)	−0.006 (2)
C15	0.023 (2)	0.047 (3)	0.034 (3)	0.000 (2)	−0.006 (2)	−0.009 (3)
C2	0.043 (3)	0.048 (4)	0.029 (3)	0.003 (3)	−0.009 (2)	0.008 (3)
C9	0.021 (2)	0.037 (3)	0.026 (3)	0.002 (2)	−0.002 (2)	−0.006 (2)
C1	0.028 (3)	0.042 (3)	0.030 (3)	0.004 (3)	0.000 (2)	−0.001 (2)
C14	0.027 (2)	0.040 (3)	0.017 (2)	−0.003 (2)	−0.0031 (19)	0.001 (2)
C10	0.020 (2)	0.035 (3)	0.027 (2)	0.001 (2)	−0.0028 (19)	−0.005 (2)
C8	0.021 (2)	0.033 (3)	0.028 (2)	0.000 (2)	−0.0051 (19)	−0.007 (2)
C7	0.029 (3)	0.043 (3)	0.026 (2)	0.002 (3)	−0.003 (2)	−0.003 (2)
C13	0.047 (4)	0.051 (4)	0.055 (5)	−0.007 (3)	−0.001 (3)	−0.005 (3)
C6	0.046 (3)	0.042 (3)	0.029 (3)	−0.002 (3)	0.000 (2)	0.001 (2)
C4	0.053 (4)	0.075 (5)	0.029 (3)	−0.011 (4)	−0.016 (3)	0.001 (3)
C17	0.044 (3)	0.037 (3)	0.026 (3)	−0.012 (3)	−0.017 (2)	−0.002 (2)
C5	0.034 (3)	0.039 (3)	0.033 (3)	−0.001 (3)	−0.002 (2)	−0.003 (2)
C18	0.027 (3)	0.048 (4)	0.036 (3)	−0.009 (3)	−0.004 (2)	0.004 (3)
C16	0.034 (3)	0.054 (4)	0.028 (3)	0.001 (3)	0.002 (2)	−0.008 (3)
C19	0.035 (3)	0.049 (3)	0.025 (3)	−0.004 (3)	−0.004 (2)	−0.002 (2)
C3	0.038 (3)	0.055 (4)	0.023 (3)	−0.001 (3)	−0.008 (2)	0.002 (3)
B	0.028 (3)	0.047 (4)	0.028 (3)	−0.006 (3)	−0.002 (2)	−0.007 (3)
C12	0.047 (3)	0.061 (4)	0.032 (3)	−0.007 (3)	−0.015 (3)	0.012 (3)
C11A	0.038 (3)	0.044 (4)	0.044 (3)	0.000 (3)	−0.001 (3)	0.003 (3)

I—C17	2.089 (5)	C7—C12	1.500 (7)
F1—B	1.397 (7)	C13—C5	1.483 (9)
N2—C3	1.352 (8)	C13—H15B	0.9600
N2—C10	1.393 (7)	C13—H15C	0.9600
N2—B	1.546 (9)	C13—H15A	0.9600
F2—B	1.373 (8)	C6—C5	1.399 (8)
N1—C5	1.337 (8)	C6—H16	0.9300
N1—C8	1.403 (6)	C4—C3	1.486 (8)
N1—B	1.544 (8)	C4—H17C	0.9600
C15—C16	1.387 (8)	C4—H17A	0.9600
C15—C14	1.392 (7)	C4—H17B	0.9600
C15—H6	0.9300	C17—C16	1.386 (8)
C2—C1	1.382 (8)	C17—C18	1.394 (8)
C2—C3	1.390 (9)	C18—C19	1.386 (8)
C2—H7	0.9300	C18—H20	0.9300
C9—C8	1.396 (8)	C16—H21	0.9300
C9—C10	1.402 (7)	C19—H22	0.9300
C9—C14	1.485 (7)	C12—H25A	0.9600
C1—C10	1.422 (8)	C12—H25C	0.9600
C1—C11A	1.494 (8)	C12—H25B	0.9600
C14—C19	1.385 (8)	C11A—H1AB	0.9600
C8—C7	1.422 (8)	C11A—H1AC	0.9600
C7—C6	1.370 (9)	C11A—H1AA	0.9600
C3—N2—C10	107.9 (5)	H17C—C4—H17A	109.5
C3—N2—B	125.6 (5)	C3—C4—H17B	109.5
C10—N2—B	126.4 (5)	H17C—C4—H17B	109.5
C5—N1—C8	108.6 (4)	H17A—C4—H17B	109.5
C5—N1—B	125.9 (5)	C16—C17—C18	120.5 (5)
C8—N1—B	125.4 (5)	C16—C17—I	119.6 (4)
C16—C15—C14	121.2 (5)	C18—C17—I	119.9 (4)
C16—C15—H6	119.4	N1—C5—C6	108.8 (5)
C14—C15—H6	119.4	N1—C5—C13	124.2 (5)
C1—C2—C3	109.1 (5)	C6—C5—C13	127.0 (6)
C1—C2—H7	125.5	C19—C18—C17	119.4 (5)
C3—C2—H7	125.5	C19—C18—H20	120.3
C8—C9—C10	120.9 (5)	C17—C18—H20	120.3
C8—C9—C14	118.1 (5)	C17—C16—C15	119.2 (5)
C10—C9—C14	120.8 (5)	C17—C16—H21	120.4
C2—C1—C10	105.7 (5)	C15—C16—H21	120.4
C2—C1—C11A	124.5 (6)	C14—C19—C18	121.0 (5)
C10—C1—C11A	129.9 (5)	C14—C19—H22	119.5
C19—C14—C15	118.7 (5)	C18—C19—H22	119.5
C19—C14—C9	121.7 (5)	N2—C3—C2	109.0 (5)
C15—C14—C9	119.6 (4)	N2—C3—C4	122.9 (6)
N2—C10—C9	120.0 (5)	C2—C3—C4	128.0 (6)
N2—C10—C1	108.3 (5)	F2—B—F1	109.5 (5)
C9—C10—C1	131.7 (5)	F2—B—N1	110.8 (5)
C9—C8—N1	120.6 (5)	F1—B—N1	109.7 (5)
C9—C8—C7	132.1 (5)	F2—B—N2	110.6 (5)
N1—C8—C7	107.2 (5)	F1—B—N2	109.9 (5)
C6—C7—C8	106.4 (5)	N1—B—N2	106.4 (5)
C6—C7—C12	125.0 (6)	C7—C12—H25A	109.5
C8—C7—C12	128.5 (5)	C7—C12—H25C	109.5
C5—C13—H15B	109.5	H25A—C12—H25C	109.5
C5—C13—H15C	109.5	C7—C12—H25B	109.5
H15B—C13—H15C	109.5	H25A—C12—H25B	109.5
C5—C13—H15A	109.5	H25C—C12—H25B	109.5
H15B—C13—H15A	109.5	C1—C11A—H1AB	109.5
H15C—C13—H15A	109.5	C1—C11A—H1AC	109.5
C7—C6—C5	108.9 (5)	H1AB—C11A—H1AC	109.5
C7—C6—H16	125.5	C1—C11A—H1AA	109.5
C5—C6—H16	125.5	H1AB—C11A—H1AA	109.5
C3—C4—H17C	109.5	H1AC—C11A—H1AA	109.5
C3—C4—H17A	109.5