2-[4-(Methyl-sulfan-yl)phen-yl]naphtho[1,8-de][1,3,2]diaza-borinane.

The title compound, C(17)H(15)BN(2)S, is one member in a series of diaza-borinanes featuring substitution at the 1-, 2- and 3-positions in the nitro-gen-boron heterocycle. The dihedral angle between the mean planes of the naphthalene and phenyl ring systems is 19.86 (6)°. In the crystal structure, two C-H⋯π inter-actions link the mol-ecules into sheets which lie parallel to the bc plane. There is a π-π inter-action between each pair of centrosymmetrically related sheets [centroid-centroid distance = 3.5922 (8) Å].

Related literature

For the synthesis of the title compound, see: Slabber (2011 ▶). For the structures of related compounds and luminescence studies, see: Weber et al. (2009 ▶).

Experimental

Crystal data

C17H15BN2S

M = 290.18

Monoclinic,

a = 13.7594 (6) Å

b = 9.0545 (3) Å

c = 12.7830 (5) Å

β = 113.411 (5)°

V = 1461.46 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.40 × 0.40 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur 2 CCD diffractometer

Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.919, T max = 0.939

14782 measured reflections

4709 independent reflections

2774 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.149

S = 0.98

4709 reflections

199 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON, SHELXL97 and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014693/lw2059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014693/lw2059Isup2.hkl

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

C17H15BN2S	F(000) = 608
Mr = 290.18	Dx = 1.319 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5105 reflections
a = 13.7594 (6) Å	θ = 2.8–32.0°
b = 9.0545 (3) Å	µ = 0.21 mm−1
c = 12.7830 (5) Å	T = 296 K
β = 113.411 (5)°	Prismatic, yellow
V = 1461.46 (10) Å3	0.40 × 0.40 × 0.30 mm
Z = 4

Oxford Diffraction Xcalibur 2 CCD diffractometer	4709 independent reflections
Radiation source: fine-focus sealed tube	2774 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 8.4190 pixels mm-1	θmax = 32.1°, θmin = 2.8°
ω scans	h = −19→20
Absorption correction: multi-scan CrysAlis RED; Oxford Diffraction, 2008)	k = −12→12
Tmin = 0.919, Tmax = 0.939	l = −16→18
14782 measured reflections

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.0834P)2] where P = (Fo2 + 2Fc2)/3
4709 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
S1	0.06634 (4)	0.07477 (6)	0.41647 (4)	0.07016 (19)
N1	0.23358 (10)	0.04869 (14)	−0.03349 (11)	0.0461 (3)
H1A	0.1893 (14)	0.1126 (19)	−0.0463 (14)	0.055*
N2	0.34252 (10)	−0.14141 (14)	0.08645 (10)	0.0444 (3)
H2A	0.3614 (13)	−0.1995 (19)	0.1435 (14)	0.053*
C1	0.28153 (11)	0.03270 (15)	−0.11059 (12)	0.0402 (3)
C2	0.25289 (13)	0.11684 (18)	−0.20761 (13)	0.0509 (4)
H2	0.1989	0.1861	−0.2242	0.061*
C3	0.30433 (14)	0.09910 (17)	−0.28158 (13)	0.0534 (4)
H3	0.2833	0.1558	−0.3476	0.064*
C4	0.38422 (13)	0.00088 (17)	−0.25892 (13)	0.0485 (4)
H4	0.4181	−0.0077	−0.3087	0.058*
C5	0.49989 (12)	−0.19240 (16)	−0.13262 (12)	0.0447 (3)
H5	0.5358	−0.2034	−0.1803	0.054*
C6	0.52808 (12)	−0.27612 (16)	−0.03688 (12)	0.0461 (3)
H6	0.5829	−0.3440	−0.0203	0.055*
C7	0.47646 (12)	−0.26238 (16)	0.03701 (12)	0.0441 (3)
H7	0.4970	−0.3210	0.1020	0.053*
C8	0.39514 (11)	−0.16235 (14)	0.01405 (11)	0.0382 (3)
C9	0.36357 (11)	−0.07342 (14)	−0.08561 (11)	0.0366 (3)
C10	0.41675 (11)	−0.08885 (14)	−0.16042 (11)	0.0393 (3)
C11	0.21019 (11)	−0.00769 (16)	0.15450 (12)	0.0417 (3)
C12	0.25773 (12)	−0.05279 (17)	0.26845 (13)	0.0485 (4)
H12	0.3227	−0.1011	0.2935	0.058*
C13	0.21171 (13)	−0.02803 (18)	0.34438 (14)	0.0505 (4)
H13	0.2462	−0.0587	0.4196	0.061*
C14	0.11401 (11)	0.04254 (16)	0.31007 (13)	0.0444 (3)
C15	0.06397 (11)	0.08679 (16)	0.19740 (13)	0.0454 (3)
H15	−0.0018	0.1327	0.1724	0.054*
C16	0.11204 (11)	0.06258 (16)	0.12205 (13)	0.0448 (3)
H16	0.0777	0.0943	0.0470	0.054*
C17	−0.05682 (14)	0.1664 (2)	0.34505 (16)	0.0674 (5)
H17A	−0.0453	0.2571	0.3128	0.101*
H17B	−0.0882	0.1875	0.3984	0.101*
H17C	−0.1034	0.1042	0.2854	0.101*
B1	0.26262 (13)	−0.03403 (18)	0.06810 (14)	0.0412 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0687 (3)	0.0942 (4)	0.0586 (3)	0.0245 (3)	0.0370 (2)	0.0095 (2)
N1	0.0447 (7)	0.0488 (7)	0.0469 (7)	0.0105 (5)	0.0205 (6)	0.0060 (6)
N2	0.0530 (7)	0.0436 (7)	0.0412 (7)	0.0061 (5)	0.0237 (6)	0.0095 (5)
C1	0.0423 (7)	0.0380 (7)	0.0377 (7)	−0.0020 (6)	0.0133 (6)	−0.0009 (5)
C2	0.0560 (9)	0.0479 (9)	0.0456 (8)	0.0103 (7)	0.0167 (7)	0.0085 (7)
C3	0.0677 (11)	0.0499 (9)	0.0391 (8)	0.0042 (8)	0.0174 (7)	0.0095 (6)
C4	0.0664 (10)	0.0447 (8)	0.0380 (8)	−0.0024 (7)	0.0245 (7)	−0.0008 (6)
C5	0.0523 (9)	0.0437 (8)	0.0417 (8)	−0.0027 (6)	0.0226 (7)	−0.0071 (6)
C6	0.0487 (8)	0.0412 (8)	0.0477 (8)	0.0056 (6)	0.0182 (7)	−0.0043 (6)
C7	0.0527 (9)	0.0390 (7)	0.0399 (7)	0.0046 (6)	0.0177 (7)	0.0038 (6)
C8	0.0430 (7)	0.0346 (7)	0.0369 (7)	−0.0035 (5)	0.0158 (6)	−0.0015 (5)
C9	0.0405 (7)	0.0334 (7)	0.0331 (6)	−0.0058 (5)	0.0115 (5)	−0.0041 (5)
C10	0.0465 (8)	0.0356 (7)	0.0356 (7)	−0.0073 (6)	0.0163 (6)	−0.0066 (5)
C11	0.0407 (7)	0.0415 (7)	0.0438 (8)	−0.0018 (6)	0.0179 (6)	−0.0002 (6)
C12	0.0443 (8)	0.0541 (9)	0.0484 (8)	0.0107 (7)	0.0196 (7)	0.0055 (7)
C13	0.0499 (9)	0.0579 (9)	0.0445 (8)	0.0091 (7)	0.0196 (7)	0.0068 (7)
C14	0.0447 (8)	0.0415 (8)	0.0500 (8)	−0.0011 (6)	0.0220 (7)	−0.0008 (6)
C15	0.0368 (7)	0.0488 (8)	0.0488 (8)	0.0026 (6)	0.0152 (6)	0.0010 (6)
C16	0.0409 (7)	0.0499 (8)	0.0407 (8)	−0.0019 (6)	0.0132 (6)	0.0012 (6)
C17	0.0618 (11)	0.0654 (11)	0.0844 (13)	0.0100 (9)	0.0391 (10)	−0.0003 (10)
B1	0.0405 (8)	0.0420 (9)	0.0414 (8)	−0.0037 (6)	0.0166 (7)	−0.0013 (6)

S1—C14	1.7534 (15)	C6—H6	0.9300
S1—C17	1.7789 (18)	C7—C8	1.3775 (19)
N1—C1	1.3944 (18)	C7—H7	0.9300
N1—B1	1.412 (2)	C8—C9	1.4213 (18)
N1—H1A	0.808 (17)	C9—C10	1.4231 (18)
N2—C8	1.3961 (17)	C11—C16	1.398 (2)
N2—B1	1.416 (2)	C11—C12	1.400 (2)
N2—H2A	0.852 (17)	C11—B1	1.559 (2)
C1—C2	1.373 (2)	C12—C13	1.372 (2)
C1—C9	1.4188 (19)	C12—H12	0.9300
C2—C3	1.398 (2)	C13—C14	1.393 (2)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.353 (2)	C14—C15	1.386 (2)
C3—H3	0.9300	C15—C16	1.385 (2)
C4—C10	1.414 (2)	C15—H15	0.9300
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.359 (2)	C17—H17A	0.9600
C5—C10	1.411 (2)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—C7	1.3948 (19)
C14—S1—C17	104.67 (8)	C1—C9—C10	119.39 (12)
C1—N1—B1	123.67 (13)	C8—C9—C10	119.41 (12)
C1—N1—H1A	117.5 (12)	C5—C10—C4	122.98 (13)
B1—N1—H1A	118.8 (12)	C5—C10—C9	118.55 (12)
C8—N2—B1	123.82 (12)	C4—C10—C9	118.48 (13)
C8—N2—H2A	115.0 (11)	C16—C11—C12	116.00 (13)
B1—N2—H2A	121.2 (11)	C16—C11—B1	121.58 (13)
C2—C1—N1	122.28 (13)	C12—C11—B1	122.42 (13)
C2—C1—C9	119.75 (13)	C13—C12—C11	122.17 (14)
N1—C1—C9	117.96 (12)	C13—C12—H12	118.9
C1—C2—C3	120.43 (14)	C11—C12—H12	118.9
C1—C2—H2	119.8	C12—C13—C14	120.76 (14)
C3—C2—H2	119.8	C12—C13—H13	119.6
C4—C3—C2	121.17 (14)	C14—C13—H13	119.6
C4—C3—H3	119.4	C15—C14—C13	118.60 (13)
C2—C3—H3	119.4	C15—C14—S1	124.99 (11)
C3—C4—C10	120.75 (14)	C13—C14—S1	116.35 (12)
C3—C4—H4	119.6	C16—C15—C14	119.96 (13)
C10—C4—H4	119.6	C16—C15—H15	120.0
C6—C5—C10	120.69 (13)	C14—C15—H15	120.0
C6—C5—H5	119.7	C15—C16—C11	122.50 (14)
C10—C5—H5	119.7	C15—C16—H16	118.7
C5—C6—C7	121.36 (14)	C11—C16—H16	118.7
C5—C6—H6	119.3	S1—C17—H17A	109.5
C7—C6—H6	119.3	S1—C17—H17B	109.5
C8—C7—C6	120.23 (13)	H17A—C17—H17B	109.5
C8—C7—H7	119.9	S1—C17—H17C	109.5
C6—C7—H7	119.9	H17A—C17—H17C	109.5
C7—C8—N2	122.63 (12)	H17B—C17—H17C	109.5
C7—C8—C9	119.77 (12)	N1—B1—N2	115.72 (13)
N2—C8—C9	117.58 (12)	N1—B1—C11	121.92 (13)
C1—C9—C8	121.19 (12)	N2—B1—C11	122.36 (13)
B1—N1—C1—C2	−178.71 (15)	C1—C9—C10—C5	178.43 (12)
B1—N1—C1—C9	0.4 (2)	C8—C9—C10—C5	−0.22 (18)
N1—C1—C2—C3	178.83 (14)	C1—C9—C10—C4	−1.23 (19)
C9—C1—C2—C3	−0.3 (2)	C8—C9—C10—C4	−179.88 (12)
C1—C2—C3—C4	−1.0 (2)	C16—C11—C12—C13	−0.8 (2)
C2—C3—C4—C10	1.2 (2)	B1—C11—C12—C13	179.34 (14)
C10—C5—C6—C7	−0.2 (2)	C11—C12—C13—C14	0.7 (2)
C5—C6—C7—C8	−0.1 (2)	C12—C13—C14—C15	0.2 (2)
C6—C7—C8—N2	−178.36 (13)	C12—C13—C14—S1	−177.34 (12)
C6—C7—C8—C9	0.3 (2)	C17—S1—C14—C15	2.01 (16)
B1—N2—C8—C7	176.50 (14)	C17—S1—C14—C13	179.41 (13)
B1—N2—C8—C9	−2.2 (2)	C13—C14—C15—C16	−1.0 (2)
C2—C1—C9—C8	−179.98 (13)	S1—C14—C15—C16	176.34 (11)
N1—C1—C9—C8	0.86 (19)	C14—C15—C16—C11	0.9 (2)
C2—C1—C9—C10	1.4 (2)	C12—C11—C16—C15	0.0 (2)
N1—C1—C9—C10	−177.77 (12)	B1—C11—C16—C15	179.86 (13)
C7—C8—C9—C1	−178.74 (12)	C1—N1—B1—N2	−2.4 (2)
N2—C8—C9—C1	−0.03 (19)	C1—N1—B1—C11	177.28 (13)
C7—C8—C9—C10	−0.11 (19)	C8—N2—B1—N1	3.3 (2)
N2—C8—C9—C10	178.60 (12)	C8—N2—B1—C11	−176.37 (13)
C6—C5—C10—C4	−179.96 (14)	C16—C11—B1—N1	20.3 (2)
C6—C5—C10—C9	0.4 (2)	C12—C11—B1—N1	−159.84 (15)
C3—C4—C10—C5	−179.68 (14)	C16—C11—B1—N2	−160.00 (14)
C3—C4—C10—C9	0.0 (2)	C12—C11—B1—N2	19.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg3i	0.93	2.75	3.5178 (18)	141
C12—H12···Cg2ii	0.93	2.82	3.6122 (17)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5–C9 ring and Cg3 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg3i	0.93	2.75	3.5178 (18)	141
C12—H12⋯Cg2ii	0.93	2.82	3.6122 (17)	144

Symmetry codes: (i) ; (ii) .