2-Phenyl-naphtho-[1,8-de][1,3,2]diaza-borinane.

The title compound, C(16)H(13)BN(2), is one compound in a series of diaza-borinanes featuring substitution at the 1, 2 and 3 positions in the nitro-gen-boron heterocycle. The title compound is slightly distorted from planarity, with a dihedral angle of 9.0 (5)° between the mean planes of the naphthalene system and the benzene ring. The m-carbon atom of the benzene ring exhibits the greatest deviation of 0.164 (2) Å from the 19-atom mean plane defined by all non-H atoms. The two N-B-C-C torsion angles are 6.0 (3) and 5.6 (3)°. In the crystal, mol-ecules are linked by π-π inter-actions into columns, with a distance of 3.92 (3) Å between the naphthalene ring centroids. Adjacent π-stacked columns, co-linear with the b-axis, are linked by C-H⋯π inter-actions.

Related literature

For the synthesis, see: Letsinger & Hamilton (1958 ▶); Pailer & Fenzl (1961 ▶); Kaupp et al. (2003 ▶); Slabber (2011 ▶). For related structures and luminescence studies, see: Weber et al. (2009 ▶). Changes in illuminated volume were kept to a minimum, and were taken into account (Görbitz, 1999 ▶) by the multi-scan inter-frame scaling (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶).

Experimental

Crystal data

C16H13BN2

M = 244.10

Monoclinic,

a = 11.0117 (7) Å

b = 5.4299 (2) Å

c = 11.7454 (7) Å

β = 117.574 (8)°

V = 622.52 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.45 × 0.35 × 0.35 mm

Data collection

Oxford Diffraction Xcalibur 2 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002 ▶) T min = 0.966, T max = 0.974

6492 measured reflections

2177 independent reflections

1601 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.121

S = 0.91

2173 reflections

173 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2002 ▶5); cell refinement: CrysAlis RED (Oxford Diffraction, 2002 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026985/fj2411sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026985/fj2411Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026985/fj2411Isup3.cml

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

C16H13BN2	F(000) = 256
Mr = 244.10	Dx = 1.302 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3114 reflections
a = 11.0117 (7) Å	θ = 3.5–32.1°
b = 5.4299 (2) Å	µ = 0.08 mm−1
c = 11.7454 (7) Å	T = 298 K
β = 117.574 (8)°	Amorphous, colourless
V = 622.52 (7) Å3	0.45 × 0.35 × 0.35 mm
Z = 2

Oxford Diffraction Xcalibur 2 CCD diffractometer	1601 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω/2θ scans	θmax = 32.2°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2002)	h = −16→16
Tmin = 0.966, Tmax = 0.974	k = −6→7
6492 measured reflections	l = −17→17
2177 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.09P)2 + 0.01P], where P = [max(Fo2,0) + 2Fc2]/3
wR(F2) = 0.121	(Δ/σ)max = 0.000415
S = 0.91	Δρmax = 0.20 e Å−3
2173 reflections	Δρmin = −0.16 e Å−3
173 parameters	Extinction correction: Larson (1970), Equation 22
1 restraint	Extinction coefficient: 140 (30)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
N1	1.07937 (13)	0.0122 (3)	0.90876 (12)	0.0456
C9	0.94717 (15)	0.0472 (3)	0.80805 (13)	0.0417
C10	0.92753 (16)	0.2405 (3)	0.71948 (14)	0.0406
C1	1.03776 (16)	0.3948 (3)	0.73368 (14)	0.0430
N2	1.16544 (14)	0.3539 (3)	0.83909 (13)	0.0491
B	1.19265 (18)	0.1616 (4)	0.92917 (17)	0.0403
C11	1.33755 (15)	0.1227 (3)	1.04553 (14)	0.0399
C12	1.44379 (16)	0.2892 (3)	1.07293 (15)	0.0477
C13	1.57062 (17)	0.2611 (4)	1.17915 (16)	0.0531
C14	1.59475 (16)	0.0640 (4)	1.26062 (15)	0.0511
C15	1.49189 (18)	−0.1046 (4)	1.23488 (17)	0.0560
C16	1.36508 (17)	−0.0755 (3)	1.12917 (17)	0.0517
C2	1.01683 (19)	0.5787 (4)	0.64568 (17)	0.0543
C3	0.8862 (2)	0.6115 (4)	0.54197 (17)	0.0612
C4	0.7787 (2)	0.4684 (4)	0.52663 (17)	0.0583
C5	0.79515 (16)	0.2780 (4)	0.61455 (14)	0.0475
C6	0.68699 (17)	0.1231 (4)	0.60321 (17)	0.0561
C7	0.70890 (17)	−0.0588 (4)	0.68964 (17)	0.0580
C8	0.83880 (17)	−0.0999 (4)	0.79292 (16)	0.0522
H12	1.4293	0.4288	1.0166	0.0546*
H13	1.6423	0.3824	1.1956	0.0605*
H14	1.6813	0.0443	1.3339	0.0599*
H15	1.5087	−0.2397	1.2902	0.0629*
H16	1.2954	−0.1980	1.1133	0.0628*
H2	1.0918	0.6844	0.6551	0.0617*
H3	0.8736	0.7378	0.4805	0.0712*
H4	0.6920	0.4919	0.4565	0.0616*
H6	0.5982	0.1487	0.5315	0.0599*
H7	0.6355	−0.1652	0.6800	0.0684*
H8	0.8547	−0.2320	0.8529	0.0600*
H101	1.0917	−0.1139	0.9595	0.0510*
H102	1.2340	0.4503	0.8471	0.0527*

	U11	U22	U33	U12	U13	U23
N1	0.0460 (7)	0.0460 (7)	0.0388 (6)	−0.0010 (6)	0.0146 (5)	0.0082 (6)
C9	0.0420 (7)	0.0475 (9)	0.0358 (7)	0.0013 (7)	0.0182 (6)	−0.0005 (7)
C10	0.0424 (7)	0.0452 (9)	0.0354 (6)	0.0063 (7)	0.0190 (6)	0.0001 (6)
C1	0.0453 (8)	0.0455 (8)	0.0400 (7)	0.0084 (7)	0.0212 (6)	0.0054 (7)
N2	0.0402 (6)	0.0529 (9)	0.0506 (7)	0.0006 (6)	0.0180 (6)	0.0130 (6)
B	0.0415 (8)	0.0417 (9)	0.0387 (8)	0.0033 (7)	0.0194 (6)	0.0029 (7)
C11	0.0411 (7)	0.0403 (8)	0.0391 (7)	0.0041 (6)	0.0193 (6)	0.0031 (6)
C12	0.0479 (8)	0.0481 (9)	0.0445 (7)	0.0000 (8)	0.0191 (6)	0.0051 (8)
C13	0.0450 (8)	0.0589 (11)	0.0517 (9)	−0.0047 (8)	0.0191 (7)	−0.0027 (8)
C14	0.0421 (8)	0.0626 (11)	0.0430 (7)	0.0078 (8)	0.0150 (6)	0.0010 (8)
C15	0.0526 (9)	0.0582 (11)	0.0528 (9)	0.0112 (9)	0.0206 (7)	0.0179 (9)
C16	0.0452 (8)	0.0493 (10)	0.0555 (9)	0.0015 (8)	0.0190 (7)	0.0128 (8)
C2	0.0590 (9)	0.0540 (10)	0.0541 (9)	0.0104 (8)	0.0297 (8)	0.0142 (8)
C3	0.0716 (11)	0.0607 (11)	0.0490 (9)	0.0188 (10)	0.0260 (8)	0.0179 (9)
C4	0.0565 (9)	0.0651 (12)	0.0421 (8)	0.0178 (9)	0.0134 (7)	0.0059 (8)
C5	0.0463 (8)	0.0558 (10)	0.0374 (7)	0.0110 (8)	0.0168 (6)	−0.0022 (7)
C6	0.0422 (8)	0.0732 (12)	0.0455 (8)	0.0055 (9)	0.0141 (6)	−0.0074 (9)
C7	0.0454 (8)	0.0729 (13)	0.0548 (9)	−0.0082 (9)	0.0225 (7)	−0.0070 (9)
C8	0.0495 (9)	0.0610 (11)	0.0488 (8)	−0.0036 (8)	0.0250 (7)	0.0012 (8)

N1—C9	1.4001 (18)	C14—C15	1.376 (3)
N1—B	1.412 (2)	C14—H14	0.949
N1—H101	0.876	C15—C16	1.383 (2)
C9—C10	1.422 (2)	C15—H15	0.940
C9—C8	1.377 (2)	C16—H16	0.966
C10—C1	1.420 (2)	C2—C3	1.401 (2)
C10—C5	1.422 (2)	C2—H2	0.969
C1—N2	1.3956 (19)	C3—C4	1.356 (3)
C1—C2	1.378 (2)	C3—H3	0.958
N2—B	1.416 (2)	C4—C5	1.412 (3)
N2—H102	0.888	C4—H4	0.937
B—C11	1.562 (2)	C5—C6	1.413 (3)
C11—C12	1.393 (2)	C6—C7	1.356 (3)
C11—C16	1.393 (2)	C6—H6	0.961
C12—C13	1.385 (2)	C7—C8	1.400 (2)
C12—H12	0.969	C7—H7	0.956
C13—C14	1.377 (3)	C8—H8	0.963
C13—H13	0.976
C9—N1—B	123.84 (13)	C15—C14—H14	120.2
C9—N1—H101	117.0	C14—C15—C16	120.50 (17)
B—N1—H101	119.1	C14—C15—H15	119.3
N1—C9—C10	117.69 (13)	C16—C15—H15	120.2
N1—C9—C8	122.02 (14)	C11—C16—C15	121.42 (16)
C10—C9—C8	120.29 (14)	C11—C16—H16	120.1
C9—C10—C1	121.16 (12)	C15—C16—H16	118.4
C9—C10—C5	119.17 (14)	C1—C2—C3	119.49 (18)
C1—C10—C5	119.67 (14)	C1—C2—H2	120.4
C10—C1—N2	117.75 (13)	C3—C2—H2	120.1
C10—C1—C2	120.18 (14)	C2—C3—C4	121.63 (18)
N2—C1—C2	122.08 (15)	C2—C3—H3	118.6
C1—N2—B	123.93 (14)	C4—C3—H3	119.8
C1—N2—H102	117.3	C3—C4—C5	120.91 (16)
B—N2—H102	118.7	C3—C4—H4	120.7
N2—B—N1	115.57 (13)	C5—C4—H4	118.4
N2—B—C11	122.03 (14)	C10—C5—C4	118.13 (16)
N1—B—C11	122.37 (13)	C10—C5—C6	118.52 (16)
B—C11—C12	121.53 (14)	C4—C5—C6	123.35 (16)
B—C11—C16	121.48 (14)	C5—C6—C7	120.87 (16)
C12—C11—C16	116.95 (14)	C5—C6—H6	117.9
C11—C12—C13	121.70 (16)	C7—C6—H6	121.2
C11—C12—H12	119.6	C6—C7—C8	121.40 (17)
C13—C12—H12	118.7	C6—C7—H7	120.3
C12—C13—C14	120.09 (17)	C8—C7—H7	118.3
C12—C13—H13	119.3	C7—C8—C9	119.74 (17)
C14—C13—H13	120.6	C7—C8—H8	121.3
C13—C14—C15	119.32 (15)	C9—C8—H8	119.0
C13—C14—H14	120.5

Cg3 is he centroid of the C11–C16 ring.

D—H···A

—···

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is he centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg3i	0.97	2.86	3.630 (2)	136

Symmetry code: (i) .