8-{4-[N,N-Bis(2-chloro­ethyl)amino]phenyl}-4,4-difluoro-1,3,5,7-tetra­methyl-4-bora-3a,4a-diaza-s-indacene

Tian, M.-Z.; Gao, S.; Peng, X.-J.

doi:10.1107/S1600536807030231

8-{4-[N,N-Bis(2-chloroethyl)amino]phenyl}-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene

In the title compound, C₂₃H₂₆BCl₂F₂N₃, the three borondipyrromethene (BODIPY) fused heterocyclic rings are almost planar [r.m.s. deviation = 0.024 (9) Å]. The dihedral angle between the planes of the benzene ring and the BODIPY fused-ring fragment is 74.9 (8)°. The sp³-hybridized B centre appears as a slightly distorted tetrahedron, with N-B-N and F-B-F angles of 106.82 (15) and 109.83 (17)°, respectively. The two B-N distances in the central ring are almost identical, indicating delocalization of their charge. The two Cl atoms are disordered, with occupancies of approximately 0.85:0.15 and 0.60:0.40.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030231/pk2028sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030231/pk2028Isup2.hkl Contains datablock I

CCDC reference: 655038

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R factor = 0.058
wR factor = 0.178
Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         20 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        100 Deg.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C21'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C23'
PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.

Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         13

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Boron-dipyrromethene (BODIPY) dyes are well known and have attracted much interest in the design of fluorescence labels (Stavis et al., 2005; Teske et al., 2006; Yee et al., 2005) and molecular fluorescence sensors (Peng et al., 2007). Detailed information on their molecular and crystal structures is necessary to understand their photophysical and photochemical properties (Yu et al., 2007). As part of our work on BODIPY compounds, we report here the synthesis and crystal structure (Fig.1) of the title compound.

As shown in Fig.1, the main skeleton of the molecule, which is formed from three fused heterocyclic rings, is close to planar with an r.m.s. deviation of 0.024 (9) Å. The maximum deviations from the mean plane for C4, C2 and N1 are 0.043 (3) Å, 0.043 (1) Å and 0.045 (0) Å, respectively. The two B—N bond lengths are nearly the same, indicating delocalization of the charge on them. Due to steric repulsion from the C1 and C10 methyl groups, the phenyl ring is twisted out of the plane of the BODIPY fused-ring system leading to a dihedral angle of 74.9 (8)° between phenyl and BODIPY groups. The two chlorine atoms are disordered with refined major:minor occupancies of 0.851 (8):0.149 (8) and 0.605 (19):0.395 (19) for Cl1/Cl1' and Cl2/Cl2' respectively.

Related literature top

For related literature, see: Stavis et al., (2005); Teske et al., (2006); Yee et al., (2005); Peng et al., (2007); Yu et al., (2007).

Experimental top

2,4-Dimethylpyrrole (2.16 ml) and 4-[N,N-Bis(2-chloroethyl)amino]benzaldehyde (3.04 g) were added to CH₂Cl₂ (800 ml) in a 1 l round-bottom flask. The mixture was bubbled with N₂ and trifluoroacetic acid (0.19 ml) was added and then stirred for 1.5 h. The resulting solution was washed with 0.1 M NaOH (200 ml) and then water (200 ml), dried over anhydrous Na₂SO₄, and filtered, and the solvent was evaporated on a rotary evaporator. The resultant product was immediately redissolved in toluene (50 ml), and p-chloranil (2.73 g) was added. After the mixture stirred for 10 min, triethylamine (8 ml), and boron trifluoride etherate (7 ml) were added. The mixture was stirred for 1.5 h, poured into water, and extracted with toluene. The toluene solution was extracted three times with 100 ml portions of water, and the solvent was evaporated on a rotary evaporator. The residue was redissolved in chloroform and subjected to silica gel flash column chromatography. Elution with EtOAc/hexane(1:8, v/v) yielded 2.18 g of the title compound (38.03%).

Structure description top

For related literature, see: Stavis et al., (2005); Teske et al., (2006); Yee et al., (2005); Peng et al., (2007); Yu et al., (2007).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SMART; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level. Both chlorine atoms are disordered with occupancy factors of 0.851 (8):0.149 (8) and 0.605 (19):0.395 (19) for Cl1/Cl1' and Cl2/Cl2' respectively.

8-{4-[N,N-Bis(2-chloroethyl)amino]phenyl}-4,4-difluoro- 1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene top

Crystal data top

C₂₃H₂₆BCl₂F₂N₃	Z = 2
M_r = 464.18	F(000) = 484
Triclinic, P1	D_x = 1.317 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2673 (2) Å	Cell parameters from 3630 reflections
b = 12.3571 (2) Å	θ = 2.3–27.5°
c = 13.2963 (2) Å	µ = 0.31 mm⁻¹
α = 92.650 (1)°	T = 298 K
β = 101.089 (1)°	Block, brown red
γ = 90.205 (1)°	0.55 × 0.35 × 0.35 mm
V = 1170.40 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3776 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.016
Graphite monochromator	θ_max = 27.5°, θ_min = 2.3°
φ and ω scans	h = −7→9
10164 measured reflections	k = −16→15
5337 independent reflections	l = −17→16

Refinement top

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)] = 0.058	H-atom parameters constrained
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.0997P)² + 0.2019P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5337 reflections	Δρ_max = 0.36 e Å⁻³
299 parameters	Δρ_min = −0.47 e Å⁻³
13 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.029 (4)

Crystal data top

C₂₃H₂₆BCl₂F₂N₃	γ = 90.205 (1)°
M_r = 464.18	V = 1170.40 (4) Å³
Triclinic, P1	Z = 2
a = 7.2673 (2) Å	Mo Kα radiation
b = 12.3571 (2) Å	µ = 0.31 mm⁻¹
c = 13.2963 (2) Å	T = 298 K
α = 92.650 (1)°	0.55 × 0.35 × 0.35 mm
β = 101.089 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3776 reflections with I > 2σ(I)
10164 measured reflections	R_int = 0.016
5337 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	13 restraints
wR(F²) = 0.178	H-atom parameters constrained
S = 1.03	Δρ_max = 0.36 e Å⁻³
5337 reflections	Δρ_min = −0.47 e Å⁻³
299 parameters

Special details top

Experimental. ¹H NMR (CDCl₃, 400 MHz, Me₄Si): δ 1.46 (s, 6H, CH₃–H), 2.55 (s, 6H, CH₃–H), 3.66 (t, 4H, ClCH₂–H), 3.78 (t, 4H, NCH₂–H), 5.98 (s, 2H, pyrrole–H), 6.78 (d, 2H, Ar–H), 7.11 (d, 2H, Ar–H). ¹³C NMR (CDCl₃, 400 MHz, Me₄Si): δ 14.76, 14.86, 40.42, 53.62, 112.38, 121.21, 124.01, 129.64, 132.20, 142.37, 143.24, 146.79, 155.26. HRMS (TOF MS EI⁺): 486.1463, calculated: 486.1483.

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.5707 (2)	0.89735 (12)	0.76379 (11)	0.0478 (4)
N2	0.2896 (2)	0.77838 (13)	0.74161 (11)	0.0489 (4)
N3	0.5791 (3)	0.64166 (13)	0.21042 (12)	0.0601 (4)
B1	0.4133 (3)	0.85947 (19)	0.81732 (17)	0.0539 (5)
F1	0.4908 (2)	0.80832 (12)	0.90633 (9)	0.0805 (4)
F2	0.30906 (19)	0.94655 (11)	0.84098 (12)	0.0804 (4)
C1	0.1105 (3)	0.6381 (2)	0.48592 (18)	0.0703 (6)
H1A	0.1946	0.5808	0.4753	0.105*
H1B	0.1209	0.6947	0.4403	0.105*
H1C	−0.0159	0.6103	0.4725	0.105*
C2	0.1600 (3)	0.68206 (16)	0.59418 (15)	0.0545 (4)
C3	0.0532 (3)	0.66843 (18)	0.66860 (18)	0.0627 (5)
H3	−0.0553	0.6261	0.6603	0.075*
C4	0.1330 (3)	0.72743 (17)	0.75713 (17)	0.0584 (5)
C5	0.0672 (4)	0.7367 (2)	0.8574 (2)	0.0809 (7)
H5A	0.1515	0.6987	0.9080	0.121*
H5B	−0.0564	0.7058	0.8489	0.121*
H5C	0.0646	0.8117	0.8793	0.121*
C6	0.7403 (4)	1.0122 (2)	0.91238 (18)	0.0775 (7)
H6A	0.6195	1.0272	0.9286	0.116*
H6B	0.8118	1.0784	0.9173	0.116*
H6C	0.8052	0.9624	0.9598	0.116*
C7	0.7161 (3)	0.96361 (16)	0.80636 (16)	0.0573 (5)
C8	0.8329 (3)	0.97433 (17)	0.73636 (18)	0.0627 (5)
H8	0.9422	1.0162	0.7474	0.075*
C9	0.7617 (3)	0.91306 (15)	0.64747 (16)	0.0542 (5)
C10	0.8506 (3)	0.9042 (2)	0.5557 (2)	0.0727 (6)
H10A	0.7881	0.9512	0.5047	0.109*
H10B	0.8406	0.8308	0.5282	0.109*
H10C	0.9805	0.9251	0.5749	0.109*
C11	0.5935 (2)	0.86418 (14)	0.66511 (13)	0.0456 (4)
C12	0.4655 (2)	0.79184 (13)	0.60480 (12)	0.0432 (4)
C13	0.3126 (2)	0.75103 (14)	0.64168 (13)	0.0465 (4)
C14	0.4939 (2)	0.75405 (14)	0.50174 (13)	0.0457 (4)
C15	0.4565 (3)	0.81847 (16)	0.41816 (15)	0.0613 (5)
H15	0.4119	0.8881	0.4266	0.074*
C16	0.4836 (4)	0.78230 (17)	0.32286 (15)	0.0668 (6)
H16	0.4575	0.8282	0.2685	0.080*
C17	0.5494 (3)	0.67820 (15)	0.30565 (13)	0.0496 (4)
C18	0.5851 (3)	0.61276 (14)	0.39045 (13)	0.0470 (4)
H18	0.6279	0.5427	0.3823	0.056*
C19	0.5580 (2)	0.65029 (14)	0.48527 (13)	0.0453 (4)
H19	0.5832	0.6049	0.5400	0.054*
C20	0.6060 (4)	0.52832 (19)	0.18816 (17)	0.0719 (6)
H20A	0.7034	0.5016	0.2413	0.086*
H20B	0.6492	0.5202	0.1236	0.086*
C21	0.4299 (5)	0.4592 (2)	0.1811 (2)	0.0951 (9)	0.851 (8)
H21A	0.3871	0.4655	0.2459	0.114*	0.851 (8)
H21B	0.4590	0.3838	0.1686	0.114*	0.851 (8)
Cl1	0.24906 (19)	0.49980 (10)	0.08129 (12)	0.0987 (6)	0.851 (8)
C21'	0.4299 (5)	0.4592 (2)	0.1811 (2)	0.0951 (9)	0.149 (8)
H21C	0.4203	0.4416	0.2503	0.114*	0.149 (8)
H21D	0.4479	0.3916	0.1444	0.114*	0.149 (8)
Cl1'	0.2157 (19)	0.5112 (12)	0.123 (2)	0.177 (5)*	0.149 (8)
C22	0.5763 (4)	0.7157 (2)	0.12880 (15)	0.0736 (6)
H22A	0.4616	0.7571	0.1212	0.088*
H22B	0.5743	0.6740	0.0650	0.088*
C23	0.7391 (5)	0.7925 (2)	0.1464 (2)	0.1021 (10)	0.605 (19)
H23A	0.7473	0.8303	0.2127	0.122*	0.605 (19)
H23B	0.7181	0.8460	0.0944	0.122*	0.605 (19)
Cl2	0.9506 (7)	0.7285 (3)	0.1428 (6)	0.1265 (15)	0.605 (19)
C23'	0.7391 (5)	0.7925 (2)	0.1464 (2)	0.1021 (10)	0.395 (19)
H23C	0.7273	0.8447	0.2014	0.122*	0.395 (19)
H23D	0.7384	0.8317	0.0848	0.122*	0.395 (19)
Cl2'	0.9593 (12)	0.7225 (7)	0.1794 (12)	0.170 (3)	0.395 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0511 (8)	0.0480 (8)	0.0430 (8)	−0.0007 (6)	0.0059 (6)	0.0008 (6)
N2	0.0529 (8)	0.0517 (8)	0.0445 (8)	−0.0005 (6)	0.0150 (6)	0.0039 (6)
N3	0.0892 (12)	0.0533 (9)	0.0410 (8)	0.0024 (8)	0.0203 (8)	0.0029 (7)
B1	0.0622 (12)	0.0569 (12)	0.0440 (11)	−0.0007 (10)	0.0148 (9)	−0.0005 (9)
F1	0.1003 (10)	0.0957 (10)	0.0423 (6)	−0.0168 (8)	0.0036 (6)	0.0149 (6)
F2	0.0800 (9)	0.0718 (8)	0.0938 (10)	0.0025 (7)	0.0346 (7)	−0.0246 (7)
C1	0.0573 (12)	0.0789 (15)	0.0679 (14)	−0.0061 (10)	−0.0006 (10)	−0.0127 (11)
C2	0.0487 (10)	0.0528 (10)	0.0593 (11)	0.0008 (8)	0.0043 (8)	−0.0003 (8)
C3	0.0516 (10)	0.0631 (12)	0.0741 (14)	−0.0093 (9)	0.0142 (9)	0.0040 (10)
C4	0.0556 (10)	0.0591 (11)	0.0659 (12)	−0.0007 (9)	0.0232 (9)	0.0099 (9)
C5	0.0847 (16)	0.0926 (17)	0.0770 (16)	−0.0041 (13)	0.0432 (13)	0.0111 (13)
C6	0.0873 (16)	0.0758 (15)	0.0597 (13)	−0.0107 (12)	−0.0066 (11)	−0.0098 (11)
C7	0.0585 (11)	0.0505 (10)	0.0580 (11)	−0.0018 (8)	−0.0007 (9)	0.0029 (8)
C8	0.0554 (11)	0.0561 (11)	0.0744 (14)	−0.0096 (9)	0.0063 (10)	0.0081 (10)
C9	0.0535 (10)	0.0471 (9)	0.0644 (12)	0.0005 (8)	0.0146 (9)	0.0136 (8)
C10	0.0698 (13)	0.0726 (14)	0.0854 (16)	0.0000 (11)	0.0348 (12)	0.0221 (12)
C11	0.0486 (9)	0.0443 (9)	0.0446 (9)	0.0035 (7)	0.0097 (7)	0.0075 (7)
C12	0.0484 (9)	0.0419 (8)	0.0401 (8)	0.0069 (7)	0.0095 (7)	0.0068 (7)
C13	0.0488 (9)	0.0461 (9)	0.0441 (9)	0.0017 (7)	0.0081 (7)	0.0015 (7)
C14	0.0514 (9)	0.0458 (9)	0.0402 (9)	0.0040 (7)	0.0096 (7)	0.0037 (7)
C15	0.0917 (15)	0.0483 (10)	0.0467 (10)	0.0224 (10)	0.0180 (10)	0.0097 (8)
C16	0.1033 (17)	0.0577 (11)	0.0420 (10)	0.0247 (11)	0.0165 (10)	0.0169 (8)
C17	0.0630 (11)	0.0492 (9)	0.0375 (9)	0.0041 (8)	0.0115 (8)	0.0038 (7)
C18	0.0576 (10)	0.0406 (8)	0.0430 (9)	0.0049 (7)	0.0097 (7)	0.0030 (7)
C19	0.0518 (9)	0.0435 (9)	0.0403 (9)	0.0020 (7)	0.0067 (7)	0.0088 (7)
C20	0.1028 (17)	0.0660 (13)	0.0484 (11)	0.0183 (12)	0.0199 (11)	−0.0043 (9)
C21	0.149 (3)	0.0555 (13)	0.0733 (16)	−0.0035 (15)	0.0061 (17)	−0.0082 (12)
Cl1	0.1037 (8)	0.1132 (8)	0.0763 (8)	−0.0152 (5)	0.0128 (5)	−0.0067 (5)
C21'	0.149 (3)	0.0555 (13)	0.0733 (16)	−0.0035 (15)	0.0061 (17)	−0.0082 (12)
C22	0.1150 (19)	0.0703 (14)	0.0382 (10)	0.0052 (13)	0.0203 (11)	0.0079 (9)
C23	0.165 (3)	0.0740 (16)	0.0763 (17)	−0.0158 (18)	0.0457 (19)	0.0090 (14)
Cl2	0.127 (2)	0.1102 (19)	0.155 (3)	−0.0298 (15)	0.067 (2)	−0.018 (2)
C23'	0.165 (3)	0.0740 (16)	0.0763 (17)	−0.0158 (18)	0.0457 (19)	0.0090 (14)
Cl2'	0.108 (3)	0.194 (5)	0.215 (7)	−0.011 (3)	0.031 (4)	0.092 (5)

Geometric parameters (Å, º) top

N1—C7	1.352 (2)	C9—C11	1.426 (3)
N1—C11	1.397 (2)	C9—C10	1.486 (3)
N1—B1	1.541 (3)	C10—H10A	0.9600
N2—C4	1.354 (2)	C10—H10B	0.9600
N2—C13	1.397 (2)	C10—H10C	0.9600
N2—B1	1.542 (3)	C11—C12	1.396 (2)
N3—C17	1.381 (2)	C12—C13	1.399 (2)
N3—C20	1.440 (3)	C12—C14	1.479 (2)
N3—C22	1.449 (3)	C14—C15	1.382 (2)
B1—F2	1.377 (3)	C14—C19	1.388 (2)
B1—F1	1.390 (3)	C15—C16	1.374 (3)
C1—C2	1.491 (3)	C15—H15	0.9300
C1—H1A	0.9600	C16—C17	1.398 (3)
C1—H1B	0.9600	C16—H16	0.9300
C1—H1C	0.9600	C17—C18	1.402 (2)
C2—C3	1.385 (3)	C18—C19	1.373 (2)
C2—C13	1.425 (3)	C18—H18	0.9300
C3—C4	1.381 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.521 (4)
C4—C5	1.500 (3)	C20—H20A	0.9700
C5—H5A	0.9600	C20—H20B	0.9700
C5—H5B	0.9600	C21—Cl1	1.771 (3)
C5—H5C	0.9600	C21—H21A	0.9700
C6—C7	1.485 (3)	C21—H21B	0.9700
C6—H6A	0.9600	C22—C23	1.490 (4)
C6—H6B	0.9600	C22—H22A	0.9700
C6—H6C	0.9600	C22—H22B	0.9700
C7—C8	1.385 (3)	C23—Cl2	1.738 (6)
C8—C9	1.385 (3)	C23—H23A	0.9700
C8—H8	0.9300	C23—H23B	0.9700

C7—N1—C11	108.32 (16)	C9—C10—H10C	109.5
C7—N1—B1	125.80 (16)	H10A—C10—H10C	109.5
C11—N1—B1	125.78 (15)	H10B—C10—H10C	109.5
C4—N2—C13	108.03 (16)	C12—C11—N1	120.37 (15)
C4—N2—B1	126.30 (16)	C12—C11—C9	131.70 (17)
C13—N2—B1	125.52 (15)	N1—C11—C9	107.89 (16)
C17—N3—C20	120.94 (16)	C11—C12—C13	120.92 (16)
C17—N3—C22	120.87 (17)	C11—C12—C14	120.12 (15)
C20—N3—C22	118.14 (17)	C13—C12—C14	118.92 (15)
F2—B1—F1	109.83 (17)	N2—C13—C12	120.45 (16)
F2—B1—N1	110.24 (17)	N2—C13—C2	108.03 (16)
F1—B1—N1	109.69 (17)	C12—C13—C2	131.52 (17)
F2—B1—N2	110.44 (17)	C15—C14—C19	117.18 (16)
F1—B1—N2	109.78 (17)	C15—C14—C12	122.32 (15)
N1—B1—N2	106.82 (15)	C19—C14—C12	120.50 (15)
C2—C1—H1A	109.5	C16—C15—C14	121.69 (17)
C2—C1—H1B	109.5	C16—C15—H15	119.2
H1A—C1—H1B	109.5	C14—C15—H15	119.2
C2—C1—H1C	109.5	C15—C16—C17	121.56 (17)
H1A—C1—H1C	109.5	C15—C16—H16	119.2
H1B—C1—H1C	109.5	C17—C16—H16	119.2
C3—C2—C13	105.50 (17)	N3—C17—C16	121.94 (16)
C3—C2—C1	125.10 (19)	N3—C17—C18	121.54 (16)
C13—C2—C1	129.27 (19)	C16—C17—C18	116.52 (16)
C4—C3—C2	109.38 (18)	C19—C18—C17	121.19 (16)
C4—C3—H3	125.3	C19—C18—H18	119.4
C2—C3—H3	125.3	C17—C18—H18	119.4
N2—C4—C3	109.04 (18)	C18—C19—C14	121.86 (15)
N2—C4—C5	122.6 (2)	C18—C19—H19	119.1
C3—C4—C5	128.32 (19)	C14—C19—H19	119.1
C4—C5—H5A	109.5	N3—C20—C21	113.8 (2)
C4—C5—H5B	109.5	N3—C20—H20A	108.8
H5A—C5—H5B	109.5	C21—C20—H20A	108.8
C4—C5—H5C	109.5	N3—C20—H20B	108.8
H5A—C5—H5C	109.5	C21—C20—H20B	108.8
H5B—C5—H5C	109.5	H20A—C20—H20B	107.7
C7—C6—H6A	109.5	C20—C21—Cl1	111.20 (19)
C7—C6—H6B	109.5	C20—C21—H21A	109.4
H6A—C6—H6B	109.5	Cl1—C21—H21A	109.4
C7—C6—H6C	109.5	C20—C21—H21B	109.4
H6A—C6—H6C	109.5	Cl1—C21—H21B	109.4
H6B—C6—H6C	109.5	H21A—C21—H21B	108.0
N1—C7—C8	108.81 (18)	N3—C22—C23	113.8 (2)
N1—C7—C6	123.2 (2)	N3—C22—H22A	108.8
C8—C7—C6	128.0 (2)	C23—C22—H22A	108.8
C9—C8—C7	109.43 (18)	N3—C22—H22B	108.8
C9—C8—H8	125.3	C23—C22—H22B	108.8
C7—C8—H8	125.3	H22A—C22—H22B	107.7
C8—C9—C11	105.54 (17)	C22—C23—Cl2	112.9 (2)
C8—C9—C10	124.60 (19)	C22—C23—H23A	109.0
C11—C9—C10	129.86 (19)	Cl2—C23—H23A	109.0
C9—C10—H10A	109.5	C22—C23—H23B	109.0
C9—C10—H10B	109.5	Cl2—C23—H23B	109.0
H10A—C10—H10B	109.5	H23A—C23—H23B	107.8

C7—N1—B1—F2	64.4 (2)	N1—C11—C12—C14	−177.88 (14)
C11—N1—B1—F2	−119.52 (19)	C9—C11—C12—C14	−0.7 (3)
C7—N1—B1—F1	−56.7 (2)	C4—N2—C13—C12	−179.44 (16)
C11—N1—B1—F1	119.42 (18)	B1—N2—C13—C12	4.9 (3)
C7—N1—B1—N2	−175.60 (16)	C4—N2—C13—C2	1.3 (2)
C11—N1—B1—N2	0.5 (2)	B1—N2—C13—C2	−174.41 (17)
C4—N2—B1—F2	−58.5 (3)	C11—C12—C13—N2	−2.8 (2)
C13—N2—B1—F2	116.38 (19)	C14—C12—C13—N2	175.01 (15)
C4—N2—B1—F1	62.7 (3)	C11—C12—C13—C2	176.29 (18)
C13—N2—B1—F1	−122.37 (19)	C14—C12—C13—C2	−5.9 (3)
C4—N2—B1—N1	−178.40 (17)	C3—C2—C13—N2	−1.4 (2)
C13—N2—B1—N1	−3.5 (2)	C1—C2—C13—N2	174.43 (19)
C13—C2—C3—C4	1.1 (2)	C3—C2—C13—C12	179.38 (18)
C1—C2—C3—C4	−175.0 (2)	C1—C2—C13—C12	−4.8 (3)
C13—N2—C4—C3	−0.6 (2)	C11—C12—C14—C15	−76.0 (2)
B1—N2—C4—C3	175.05 (18)	C13—C12—C14—C15	106.2 (2)
C13—N2—C4—C5	178.77 (19)	C11—C12—C14—C19	104.8 (2)
B1—N2—C4—C5	−5.6 (3)	C13—C12—C14—C19	−73.0 (2)
C2—C3—C4—N2	−0.3 (2)	C19—C14—C15—C16	−0.8 (3)
C2—C3—C4—C5	−179.7 (2)	C12—C14—C15—C16	180.0 (2)
C11—N1—C7—C8	0.2 (2)	C14—C15—C16—C17	0.4 (4)
B1—N1—C7—C8	176.89 (18)	C20—N3—C17—C16	−166.0 (2)
C11—N1—C7—C6	−178.47 (18)	C22—N3—C17—C16	11.4 (3)
B1—N1—C7—C6	−1.8 (3)	C20—N3—C17—C18	14.5 (3)
N1—C7—C8—C9	−0.5 (2)	C22—N3—C17—C18	−168.2 (2)
C6—C7—C8—C9	178.2 (2)	C15—C16—C17—N3	−179.2 (2)
C7—C8—C9—C11	0.5 (2)	C15—C16—C17—C18	0.3 (3)
C7—C8—C9—C10	−179.54 (19)	N3—C17—C18—C19	178.95 (18)
C7—N1—C11—C12	177.82 (16)	C16—C17—C18—C19	−0.6 (3)
B1—N1—C11—C12	1.2 (3)	C17—C18—C19—C14	0.1 (3)
C7—N1—C11—C9	0.07 (19)	C15—C14—C19—C18	0.5 (3)
B1—N1—C11—C9	−176.60 (17)	C12—C14—C19—C18	179.77 (16)
C8—C9—C11—C12	−177.74 (18)	C17—N3—C20—C21	69.8 (3)
C10—C9—C11—C12	2.3 (3)	C22—N3—C20—C21	−107.6 (2)
C8—C9—C11—N1	−0.3 (2)	N3—C20—C21—Cl1	61.2 (2)
C10—C9—C11—N1	179.69 (19)	C17—N3—C22—C23	69.9 (3)
N1—C11—C12—C13	−0.1 (2)	C20—N3—C22—C23	−112.6 (3)
C9—C11—C12—C13	177.05 (18)	N3—C22—C23—Cl2	67.2 (4)

Experimental details

Crystal data
Chemical formula	C₂₃H₂₆BCl₂F₂N₃
M_r	464.18
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.2673 (2), 12.3571 (2), 13.2963 (2)
α, β, γ (°)	92.650 (1), 101.089 (1), 90.205 (1)
V (Å³)	1170.40 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.55 × 0.35 × 0.35

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10164, 5337, 3776
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.178, 1.03
No. of reflections	5337
No. of parameters	299
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.47

Computer programs: SMART (Bruker, 2005), SMART, SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

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8-{4-[N,N-Bis(2-chloro­ethyl)amino]phenyl}-4,4-difluoro-1,3,5,7-tetra­methyl-4-bora-3a,4a-diaza-s-indacene

Supporting information

Key indicators

checkCIF/PLATON results

8-{4-[N,N-Bis(2-chloroethyl)amino]phenyl}-4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene