2-(3-Meth-oxy-phen-yl)-1,3-dihydro-1,3,2-benzodiaza-borole.

The title compound, C(13)H(13)BN(2)O, is one in a series of 1,3,2-benzodiaza-boroles featuring a 2-meth-oxy-phenyl substitution at the 2-position in the nitro-gen-boron heterocyle. The dihedral angle between the mean planes of the benzodiaza-borole and 2-meth-oxy-phenyl ring systems is 21.5 (1)°. There is an inter-molecular hydrogen bond between one of the NH groups and the meth-oxy O atom. This hydrogen bond leads to an infinite hydrogen-bonded chain colinear with the a axis.

Related literature

For the synthesis of the title compound, see: Sithebe et al. (2011 ▶); Weber et al. (2009 ▶, 2011 ▶). For related derivatives as well as their photoluminiscence studies, see: Weber et al. (2010 ▶); Maruyama & Kawanishi (2002 ▶). For structures of related compounds, see: Slabber et al. (2011 ▶); Akerman et al. (2011 ▶). For applications of 1,3,2-diaza­borolyl compounds, see: Schwedler et al. (2011 ▶).

Experimental

Crystal data

C13H13BN2O

M = 224.06

Orthorhombic,

a = 7.549 (5) Å

b = 12.230 (5) Å

c = 12.308 (5) Å

V = 1136.3 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 110 K

0.50 × 0.40 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur 2 CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.960, T max = 0.968

11586 measured reflections

2125 independent reflections

1939 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.05

2125 reflections

164 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶) and POV-RAY (Cason et al., 2002 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812028437/nk2170sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028437/nk2170Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812028437/nk2170Isup3.cml

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

C13H13BN2O	F(000) = 472
Mr = 224.06	Dx = 1.310 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1939 reflections
a = 7.549 (5) Å	θ = 3.2–32.1°
b = 12.230 (5) Å	µ = 0.08 mm−1
c = 12.308 (5) Å	T = 110 K
V = 1136.3 (10) Å3	Needle, colourless
Z = 4	0.50 × 0.40 × 0.40 mm

Oxford Diffraction Xcalibur 2 CCD diffractometer	2125 independent reflections
Radiation source: fine-focus sealed tube	1939 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans at fixed θ angles	θmax = 32.1°, θmin = 3.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −11→7
Tmin = 0.960, Tmax = 0.968	k = −17→18
11586 measured reflections	l = −18→18

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0725P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2125 reflections	Δρmax = 0.32 e Å−3
164 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.058 (6)

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

	x	y	z	Uiso*/Ueq
O001	0.68887 (13)	0.34747 (7)	1.11670 (7)	0.0238 (2)
N2	0.86812 (15)	0.17066 (8)	0.71418 (8)	0.0184 (2)
N1	0.69146 (14)	0.27984 (8)	0.61068 (8)	0.0187 (2)
C8	0.85853 (16)	0.12575 (9)	0.61012 (9)	0.0171 (2)
C2	0.73726 (16)	0.30830 (10)	0.92377 (10)	0.0179 (2)
H2	0.7848	0.2380	0.9388	0.022*
C6	0.65474 (16)	0.44957 (10)	0.79625 (10)	0.0217 (2)
H6	0.6449	0.4756	0.7238	0.026*
C11	0.78716 (17)	0.07371 (10)	0.39528 (10)	0.0208 (2)
H11	0.7634	0.0544	0.3219	0.025*
C13	0.74943 (16)	0.19384 (9)	0.54613 (9)	0.0168 (2)
C12	0.71345 (16)	0.16880 (10)	0.43846 (9)	0.0194 (2)
H12	0.6407	0.2151	0.3954	0.023*
C1	0.72155 (16)	0.34445 (10)	0.81557 (9)	0.0181 (2)
C9	0.93295 (17)	0.03188 (10)	0.56632 (11)	0.0203 (2)
H9	1.0075	−0.0139	0.6087	0.024*
C4	0.61570 (17)	0.47951 (10)	0.98828 (10)	0.0228 (3)
H4	0.5789	0.5249	1.0467	0.027*
C3	0.68309 (17)	0.37557 (10)	1.00871 (10)	0.0193 (2)
C5	0.60273 (18)	0.51624 (10)	0.88201 (11)	0.0241 (3)
H5	0.5580	0.5874	0.8677	0.029*
C10	0.89523 (17)	0.00661 (10)	0.45839 (10)	0.0213 (2)
H10	0.9442	−0.0577	0.4272	0.026*
C7	0.7662 (2)	0.24408 (11)	1.14365 (11)	0.0296 (3)
H7A	0.6947	0.1852	1.1122	0.044*
H7B	0.7700	0.2358	1.2228	0.044*
H7C	0.8868	0.2405	1.1144	0.044*
B1	0.76235 (18)	0.26817 (10)	0.71788 (10)	0.0179 (2)
H102	0.940 (3)	0.1411 (15)	0.7630 (17)	0.042 (5)*
H101	0.625 (3)	0.3271 (17)	0.5846 (18)	0.050 (6)*

	U11	U22	U33	U12	U13	U23
O001	0.0320 (5)	0.0242 (4)	0.0153 (4)	0.0015 (4)	0.0037 (4)	−0.0013 (3)
N2	0.0218 (5)	0.0184 (4)	0.0150 (4)	0.0016 (4)	−0.0021 (4)	0.0006 (3)
N1	0.0233 (5)	0.0172 (4)	0.0156 (4)	0.0040 (4)	−0.0009 (4)	0.0001 (4)
C8	0.0195 (5)	0.0166 (5)	0.0152 (5)	−0.0009 (4)	0.0005 (4)	0.0018 (4)
C2	0.0197 (5)	0.0175 (5)	0.0166 (5)	−0.0002 (4)	0.0004 (4)	−0.0011 (4)
C6	0.0237 (6)	0.0211 (5)	0.0202 (5)	0.0015 (5)	−0.0015 (5)	0.0007 (4)
C11	0.0239 (6)	0.0214 (5)	0.0172 (5)	−0.0029 (5)	0.0019 (5)	−0.0017 (4)
C13	0.0196 (5)	0.0158 (4)	0.0150 (5)	0.0004 (4)	0.0013 (4)	0.0009 (4)
C12	0.0224 (5)	0.0207 (5)	0.0151 (5)	0.0000 (4)	−0.0003 (4)	0.0006 (4)
C1	0.0188 (5)	0.0185 (5)	0.0170 (5)	−0.0006 (4)	−0.0008 (4)	−0.0006 (4)
C9	0.0219 (5)	0.0182 (5)	0.0207 (5)	0.0018 (4)	0.0015 (5)	0.0018 (4)
C4	0.0243 (6)	0.0220 (6)	0.0221 (6)	0.0024 (5)	0.0021 (5)	−0.0036 (4)
C3	0.0202 (5)	0.0210 (5)	0.0166 (5)	−0.0022 (4)	0.0010 (4)	−0.0020 (4)
C5	0.0265 (6)	0.0194 (5)	0.0265 (6)	0.0047 (5)	−0.0011 (5)	−0.0010 (5)
C10	0.0242 (6)	0.0180 (5)	0.0219 (5)	0.0004 (5)	0.0041 (5)	−0.0015 (4)
C7	0.0382 (7)	0.0313 (7)	0.0195 (5)	0.0066 (6)	0.0031 (5)	0.0052 (5)
B1	0.0202 (5)	0.0178 (5)	0.0157 (5)	−0.0005 (5)	0.0001 (5)	0.0003 (4)

O001—C3	1.3735 (15)	C11—C10	1.3937 (18)
O001—C7	1.4316 (17)	C11—C12	1.3945 (17)
N2—C8	1.3954 (15)	C11—H11	0.9500
N2—B1	1.4359 (17)	C13—C12	1.3870 (16)
N2—H102	0.89 (2)	C12—H12	0.9500
N1—C13	1.3888 (15)	C1—B1	1.5527 (18)
N1—B1	1.4309 (17)	C9—C10	1.3933 (19)
N1—H101	0.83 (2)	C9—H9	0.9500
C8—C9	1.3872 (17)	C4—C5	1.3864 (19)
C8—C13	1.4115 (16)	C4—C3	1.3921 (18)
C2—C3	1.3918 (16)	C4—H4	0.9500
C2—C1	1.4081 (17)	C5—H5	0.9500
C2—H2	0.9500	C10—H10	0.9500
C6—C5	1.3903 (18)	C7—H7A	0.9800
C6—C1	1.4013 (17)	C7—H7B	0.9800
C6—H6	0.9500	C7—H7C	0.9800
C3—O001—C7	117.27 (10)	C6—C1—B1	119.42 (11)
C8—N2—B1	109.10 (10)	C2—C1—B1	121.80 (11)
C8—N2—H102	119.5 (12)	C8—C9—C10	118.12 (12)
B1—N2—H102	131.1 (12)	C8—C9—H9	120.9
C13—N1—B1	109.52 (10)	C10—C9—H9	120.9
C13—N1—H101	119.8 (15)	C5—C4—C3	119.48 (12)
B1—N1—H101	130.7 (15)	C5—C4—H4	120.3
C9—C8—N2	131.41 (11)	C3—C4—H4	120.3
C9—C8—C13	120.51 (11)	O001—C3—C2	124.73 (11)
N2—C8—C13	108.07 (10)	O001—C3—C4	114.51 (11)
C3—C2—C1	120.01 (11)	C2—C3—C4	120.76 (12)
C3—C2—H2	120.0	C4—C5—C6	120.41 (12)
C1—C2—H2	120.0	C4—C5—H5	119.8
C5—C6—C1	120.72 (12)	C6—C5—H5	119.8
C5—C6—H6	119.6	C9—C10—C11	121.36 (12)
C1—C6—H6	119.6	C9—C10—H10	119.3
C10—C11—C12	120.81 (12)	C11—C10—H10	119.3
C10—C11—H11	119.6	O001—C7—H7A	109.5
C12—C11—H11	119.6	O001—C7—H7B	109.5
C12—C13—N1	130.70 (11)	H7A—C7—H7B	109.5
C12—C13—C8	121.14 (11)	O001—C7—H7C	109.5
N1—C13—C8	108.15 (10)	H7A—C7—H7C	109.5
C13—C12—C11	118.05 (12)	H7B—C7—H7C	109.5
C13—C12—H12	121.0	N1—B1—N2	105.16 (10)
C11—C12—H12	121.0	N1—B1—C1	125.44 (11)
C6—C1—C2	118.61 (11)	N2—B1—C1	129.33 (11)
B1—N2—C8—C9	−178.52 (13)	C7—O001—C3—C4	−176.53 (12)
B1—N2—C8—C13	0.68 (13)	C1—C2—C3—O001	178.47 (12)
B1—N1—C13—C12	178.50 (13)	C1—C2—C3—C4	−1.02 (18)
B1—N1—C13—C8	−0.17 (14)	C5—C4—C3—O001	−179.61 (12)
C9—C8—C13—C12	0.17 (18)	C5—C4—C3—C2	−0.07 (19)
N2—C8—C13—C12	−179.14 (11)	C3—C4—C5—C6	0.7 (2)
C9—C8—C13—N1	178.99 (10)	C1—C6—C5—C4	−0.2 (2)
N2—C8—C13—N1	−0.32 (13)	C8—C9—C10—C11	0.53 (18)
N1—C13—C12—C11	−178.02 (12)	C12—C11—C10—C9	0.14 (19)
C8—C13—C12—C11	0.50 (18)	C13—N1—B1—N2	0.57 (13)
C10—C11—C12—C13	−0.65 (18)	C13—N1—B1—C1	−176.89 (11)
C5—C6—C1—C2	−0.88 (19)	C8—N2—B1—N1	−0.76 (13)
C5—C6—C1—B1	174.46 (12)	C8—N2—B1—C1	176.55 (12)
C3—C2—C1—C6	1.48 (18)	C6—C1—B1—N1	−19.86 (19)
C3—C2—C1—B1	−173.75 (12)	C2—C1—B1—N1	155.33 (12)
N2—C8—C9—C10	178.44 (12)	C6—C1—B1—N2	163.32 (12)
C13—C8—C9—C10	−0.68 (17)	C2—C1—B1—N2	−21.5 (2)
C7—O001—C3—C2	3.95 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H102···O001i	0.89 (2)	2.40 (2)	3.201 (2)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H102⋯O001i	0.89 (2)	2.40 (2)	3.201 (2)	151 (2)

Symmetry code: (i) .