Difluoro-[2-(quinolin-2-yl)phenolato]borane.

The title compound, C(15)H(10)BF(2)NO, was synthesized by the reaction of 2-(quinolin-2-yl)phenol and boron trifluoride etherate. The quinoline ring system and the benzene ring are twisted, making a dihedral angle of 8.3 (2)°. In the crystal, π-π inter-actions between the aromatic rings [centroid-centroid distance = 3.638 (9) Å] link the mol-ecules into chains propagating in [100].

Related literature

For the properties and the preparation of difluoro­boron complexes, see: Loudet et al. (2007 ▶); Ulrich et al. (2008 ▶); Ono et al. (2009 ▶); Zhou et al. (2008 ▶); Xia et al. (2008 ▶).

Experimental

Crystal data

C15H10BF2NO

M = 269.05

Triclinic,

a = 7.4660 (15) Å

b = 8.6300 (17) Å

c = 9.3420 (19) Å

α = 97.71 (3)°

β = 95.63 (3)°

γ = 92.61 (3)°

V = 592.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 295 K

0.46 × 0.22 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.949, T max = 0.984

4885 measured reflections

2169 independent reflections

1329 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.127

S = 1.13

2169 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811011895/si2346sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011895/si2346Isup2.hkl

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

C15H10BF2NO	Z = 2
Mr = 269.05	F(000) = 276
Triclinic, P1	Dx = 1.508 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4660 (15) Å	Cell parameters from 3364 reflections
b = 8.6300 (17) Å	θ = 3.0–27.4°
c = 9.3420 (19) Å	µ = 0.12 mm−1
α = 97.71 (3)°	T = 295 K
β = 95.63 (3)°	Prism, yellow
γ = 92.61 (3)°	0.46 × 0.22 × 0.14 mm
V = 592.5 (2) Å3

Rigaku R-AXIS RAPID diffractometer	2169 independent reflections
Radiation source: fine-focus sealed tube	1329 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10.00 pixels mm-1	θmax = 25.4°, θmin = 3.0°
ω scans	h = −8→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −10→10
Tmin = 0.949, Tmax = 0.984	l = −11→11
4885 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) = 0.127	w = 1/[σ2(Fo2) + (0.0631P)2] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
2169 reflections	Δρmax = 0.29 e Å−3
182 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.033 (7)

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	0.38077 (17)	0.27217 (11)	0.25453 (14)	0.0696 (4)
F2	0.07658 (16)	0.22181 (12)	0.23344 (13)	0.0700 (4)
O1	0.2311 (2)	0.34773 (14)	0.44802 (16)	0.0710 (5)
N1	0.26036 (19)	0.06102 (14)	0.37319 (17)	0.0427 (4)
C1	0.3005 (2)	−0.06216 (19)	0.2687 (2)	0.0441 (5)
C2	0.3067 (3)	−0.0422 (2)	0.1235 (2)	0.0579 (6)
H2	0.2826	0.0541	0.0939	0.069*
C3	0.3479 (3)	−0.1635 (2)	0.0245 (2)	0.0640 (6)
H3	0.3524	−0.1481	−0.0718	0.077*
C4	0.3833 (3)	−0.3099 (2)	0.0649 (3)	0.0624 (6)
H4	0.4125	−0.3905	−0.0037	0.075*
C5	0.3750 (3)	−0.3344 (2)	0.2044 (3)	0.0563 (6)
H5	0.3972	−0.4322	0.2313	0.068*
C6	0.3324 (2)	−0.21077 (19)	0.3095 (2)	0.0465 (5)
C7	0.3186 (3)	−0.2317 (2)	0.4545 (2)	0.0554 (5)
H7	0.3407	−0.3284	0.4840	0.066*
C8	0.2735 (3)	−0.1123 (2)	0.5524 (2)	0.0511 (5)
H8	0.2625	−0.1285	0.6476	0.061*
C9	0.2435 (2)	0.03633 (18)	0.5099 (2)	0.0425 (4)
C10	0.1944 (2)	0.16571 (19)	0.6148 (2)	0.0441 (5)
C11	0.1542 (3)	0.1444 (2)	0.7542 (2)	0.0556 (5)
H11	0.1573	0.0449	0.7817	0.067*
C12	0.1102 (3)	0.2672 (3)	0.8516 (2)	0.0629 (6)
H12	0.0857	0.2506	0.9442	0.075*
C13	0.1024 (3)	0.4155 (2)	0.8112 (2)	0.0602 (6)
H13	0.0710	0.4983	0.8766	0.072*
C14	0.1407 (3)	0.4412 (2)	0.6757 (2)	0.0591 (6)
H14	0.1355	0.5411	0.6493	0.071*
C15	0.1874 (3)	0.3172 (2)	0.5773 (2)	0.0498 (5)
B1	0.2359 (3)	0.2321 (2)	0.3236 (3)	0.0502 (6)

	U11	U22	U33	U12	U13	U23
F1	0.0908 (10)	0.0476 (6)	0.0785 (9)	0.0031 (5)	0.0333 (7)	0.0210 (6)
F2	0.0803 (9)	0.0602 (7)	0.0707 (9)	0.0220 (6)	−0.0066 (7)	0.0181 (6)
O1	0.1229 (14)	0.0395 (7)	0.0548 (10)	0.0104 (7)	0.0259 (9)	0.0080 (6)
N1	0.0465 (9)	0.0372 (8)	0.0449 (10)	0.0025 (6)	0.0032 (7)	0.0089 (7)
C1	0.0420 (10)	0.0382 (9)	0.0508 (13)	0.0034 (7)	0.0027 (9)	0.0031 (8)
C2	0.0719 (14)	0.0489 (10)	0.0536 (14)	0.0113 (9)	0.0089 (11)	0.0057 (9)
C3	0.0769 (16)	0.0611 (12)	0.0542 (14)	0.0151 (10)	0.0107 (11)	0.0019 (10)
C4	0.0588 (13)	0.0511 (11)	0.0718 (17)	0.0090 (9)	0.0043 (11)	−0.0112 (11)
C5	0.0515 (12)	0.0393 (10)	0.0760 (16)	0.0048 (8)	0.0003 (11)	0.0044 (10)
C6	0.0384 (10)	0.0430 (10)	0.0567 (13)	−0.0010 (7)	−0.0011 (9)	0.0072 (8)
C7	0.0554 (12)	0.0402 (10)	0.0724 (15)	0.0034 (8)	0.0011 (11)	0.0179 (9)
C8	0.0569 (12)	0.0468 (10)	0.0516 (12)	0.0029 (8)	0.0018 (9)	0.0175 (9)
C9	0.0390 (10)	0.0449 (9)	0.0442 (12)	−0.0019 (7)	0.0006 (8)	0.0132 (8)
C10	0.0379 (10)	0.0442 (9)	0.0481 (12)	−0.0002 (7)	0.0004 (8)	0.0030 (8)
C11	0.0510 (12)	0.0656 (12)	0.0522 (13)	0.0037 (9)	0.0050 (10)	0.0158 (10)
C12	0.0570 (13)	0.0839 (15)	0.0485 (13)	0.0044 (10)	0.0110 (10)	0.0080 (11)
C13	0.0529 (13)	0.0657 (13)	0.0570 (15)	−0.0005 (9)	0.0095 (10)	−0.0106 (11)
C14	0.0676 (14)	0.0479 (10)	0.0603 (15)	0.0033 (9)	0.0124 (11)	−0.0023 (10)
C15	0.0556 (12)	0.0499 (11)	0.0440 (12)	−0.0009 (8)	0.0077 (10)	0.0065 (9)
B1	0.0666 (15)	0.0391 (11)	0.0489 (14)	0.0099 (9)	0.0138 (12)	0.0133 (9)

F1—B1	1.367 (3)	C6—C7	1.403 (3)
F2—B1	1.381 (3)	C7—C8	1.360 (3)
O1—C15	1.338 (2)	C7—H7	0.9300
O1—B1	1.431 (3)	C8—C9	1.414 (2)
N1—C9	1.339 (2)	C8—H8	0.9300
N1—C1	1.408 (2)	C9—C10	1.468 (3)
N1—B1	1.619 (2)	C10—C11	1.398 (3)
C1—C2	1.395 (3)	C10—C15	1.400 (3)
C1—C6	1.410 (2)	C11—C12	1.374 (3)
C2—C3	1.368 (2)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.384 (3)
C3—C4	1.396 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.369 (3)
C4—C5	1.354 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C15	1.394 (3)
C5—C6	1.420 (3)	C14—H14	0.9300
C5—H5	0.9300
Cg1···Cg2i	3.638 (9)
C15—O1—B1	124.65 (15)	N1—C9—C8	120.27 (16)
C9—N1—C1	120.50 (15)	N1—C9—C10	119.15 (16)
C9—N1—B1	121.28 (15)	C8—C9—C10	120.58 (18)
C1—N1—B1	118.22 (15)	C11—C10—C15	117.48 (17)
C2—C1—N1	121.58 (16)	C11—C10—C9	122.35 (17)
C2—C1—C6	118.53 (16)	C15—C10—C9	120.17 (18)
N1—C1—C6	119.88 (18)	C12—C11—C10	121.6 (2)
C3—C2—C1	120.35 (18)	C12—C11—H11	119.2
C3—C2—H2	119.8	C10—C11—H11	119.2
C1—C2—H2	119.8	C11—C12—C13	119.7 (2)
C2—C3—C4	121.3 (2)	C11—C12—H12	120.1
C2—C3—H3	119.3	C13—C12—H12	120.1
C4—C3—H3	119.3	C14—C13—C12	120.48 (18)
C5—C4—C3	119.90 (18)	C14—C13—H13	119.8
C5—C4—H4	120.1	C12—C13—H13	119.8
C3—C4—H4	120.1	C13—C14—C15	119.88 (19)
C4—C5—C6	120.01 (18)	C13—C14—H14	120.1
C4—C5—H5	120.0	C15—C14—H14	120.1
C6—C5—H5	120.0	O1—C15—C14	118.28 (17)
C7—C6—C1	118.21 (17)	O1—C15—C10	120.85 (16)
C7—C6—C5	121.96 (18)	C14—C15—C10	120.83 (19)
C1—C6—C5	119.83 (19)	F1—B1—F2	111.96 (18)
C8—C7—C6	120.81 (17)	F1—B1—O1	107.42 (17)
C8—C7—H7	119.6	F2—B1—O1	111.11 (16)
C6—C7—H7	119.6	F1—B1—N1	109.25 (15)
C7—C8—C9	120.25 (19)	F2—B1—N1	106.83 (15)
C7—C8—H8	119.9	O1—B1—N1	110.27 (17)
C9—C8—H8	119.9