[2,2'-Imino-diethano-lato(2-)-κO,N,O'][4-(meth-oxy-carbonyl-meth-yl)phen-yl]boron.

The title compound, C(13)H(18)BNO(4), was readily obtained from the reaction of methyl 4-boronobenzene acetate with ethano-lamine. A combination of inter-molecular N-H⋯O hydrogen bonds and C-H⋯π inter-actions leads to the pairwise association of mol-ecules.

Related literature

For background to the biological importance of boron, see: Warrington (1923 ▶); Jabbour et al. (2004 ▶). For the use of boron-containing reagents in synthetic chemistry, see: Miyaura & Suzuki (1995 ▶); Corey et al. (1987 ▶); Liu et al. (2007 ▶); Jung & Lazarova (1999 ▶); Chan et al. (1998 ▶); Evans et al. (1998 ▶); Lam et al. (1998 ▶). For related structures, see: Rettig & Trotter (1975 ▶); Wang & Georghiou (2002 ▶).

Experimental

Crystal data

C13H18BNO4

M = 263.10

Orthorhombic,

a = 8.3776 (11) Å

b = 8.9269 (11) Å

c = 17.369 (2) Å

V = 1299.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 153 K

0.30 × 0.09 × 0.06 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.985, T max = 0.997

16363 measured reflections

1725 independent reflections

1707 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.112

S = 1.17

1725 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2002 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037864/fj2337sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037864/fj2337Isup2.hkl

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

C13H18BNO4	Dx = 1.345 Mg m−3
Mr = 263.10	Melting point = 452–453 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5108 reflections
a = 8.3776 (11) Å	θ = 2.6–30.6°
b = 8.9269 (11) Å	µ = 0.10 mm−1
c = 17.369 (2) Å	T = 153 K
V = 1299.0 (3) Å3	Platelet, colorless
Z = 4	0.30 × 0.09 × 0.06 mm
F(000) = 560

Rigaku Saturn diffractometer	1725 independent reflections
Radiation source: fine-focus sealed tube	1707 reflections with I > 2σ(I)
graphite - Rigaku SHINE	Rint = 0.037
Detector resolution: 14.63 pixels mm-1	θmax = 27.5°, θmin = 2.6°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −11→11
Tmin = 0.985, Tmax = 0.997	l = −22→22
16363 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.17	w = 1/[σ2(Fo2) + (0.0529P)2 + 0.4126P] where P = (Fo2 + 2Fc2)/3
1725 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.The crystal was a weak anomalous scatterer collected with Mo Kα radiation. Friedel mates were merged (MERG 4) and the absolute configuration was not determined.

	x	y	z	Uiso*/Ueq
O1	1.00908 (19)	0.47529 (18)	0.35582 (9)	0.0281 (4)
O2	0.85897 (19)	0.47478 (17)	0.23631 (9)	0.0268 (4)
O3	0.5232 (2)	−0.2735 (2)	0.39057 (11)	0.0422 (5)
O4	0.6510 (3)	−0.2494 (3)	0.50205 (13)	0.0617 (7)
N1	1.0730 (2)	0.2952 (2)	0.25504 (10)	0.0249 (4)
H1	1.0599	0.1919	0.2577	0.030*
C1	0.7998 (3)	0.2734 (2)	0.34181 (12)	0.0243 (4)
C2	0.6576 (3)	0.2247 (3)	0.30806 (13)	0.0253 (4)
H2	0.6285	0.2624	0.2589	0.030*
C3	0.5568 (3)	0.1220 (3)	0.34475 (13)	0.0261 (5)
H3	0.4626	0.0888	0.3195	0.031*
C4	0.5932 (3)	0.0679 (3)	0.41775 (13)	0.0263 (5)
C5	0.7326 (3)	0.1174 (3)	0.45272 (13)	0.0296 (5)
H5	0.7589	0.0827	0.5028	0.035*
C6	0.8342 (3)	0.2173 (3)	0.41551 (13)	0.0276 (5)
H6	0.9294	0.2482	0.4406	0.033*
C7	1.1685 (3)	0.4963 (3)	0.33084 (14)	0.0302 (5)
H7A	1.2382	0.5254	0.3744	0.036*
H7B	1.1743	0.5747	0.2906	0.036*
C8	1.2172 (3)	0.3441 (3)	0.29856 (15)	0.0313 (5)
H8A	1.3108	0.3534	0.2641	0.038*
H8B	1.2427	0.2729	0.3405	0.038*
C9	0.8982 (3)	0.4085 (3)	0.16438 (13)	0.0283 (5)
H9A	0.8939	0.4839	0.1226	0.034*
H9B	0.8231	0.3263	0.1520	0.034*
C10	1.0671 (3)	0.3484 (3)	0.17388 (14)	0.0297 (5)
H10A	1.0875	0.2650	0.1376	0.036*
H10B	1.1469	0.4283	0.1649	0.036*
C11	0.4878 (3)	−0.0470 (3)	0.45767 (13)	0.0287 (5)
H11A	0.4717	−0.0173	0.5120	0.034*
H11B	0.3821	−0.0498	0.4323	0.034*
C12	0.5624 (3)	−0.1999 (3)	0.45463 (15)	0.0330 (5)
C13	0.5926 (4)	−0.4222 (3)	0.3835 (2)	0.0499 (8)
H13A	0.7093	−0.4143	0.3831	0.060*
H13B	0.5563	−0.4686	0.3354	0.060*
H13C	0.5589	−0.4840	0.4272	0.060*
B1	0.9234 (3)	0.3847 (3)	0.30025 (14)	0.0236 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0291 (8)	0.0257 (8)	0.0296 (8)	−0.0045 (7)	0.0027 (6)	−0.0029 (7)
O2	0.0318 (8)	0.0203 (7)	0.0283 (8)	0.0029 (7)	0.0023 (7)	0.0014 (6)
O3	0.0412 (10)	0.0352 (10)	0.0503 (10)	0.0057 (9)	−0.0049 (9)	−0.0132 (9)
O4	0.0875 (17)	0.0522 (12)	0.0453 (11)	0.0243 (14)	−0.0164 (12)	0.0011 (9)
N1	0.0271 (9)	0.0181 (8)	0.0295 (9)	0.0004 (8)	0.0027 (8)	0.0024 (8)
C1	0.0254 (10)	0.0195 (10)	0.0279 (10)	0.0014 (9)	0.0055 (8)	−0.0020 (9)
C2	0.0263 (10)	0.0228 (10)	0.0268 (10)	0.0030 (9)	0.0023 (9)	0.0005 (9)
C3	0.0232 (10)	0.0234 (10)	0.0318 (11)	0.0010 (9)	0.0011 (9)	−0.0018 (9)
C4	0.0289 (10)	0.0213 (10)	0.0286 (10)	0.0009 (9)	0.0075 (9)	−0.0026 (9)
C5	0.0360 (12)	0.0291 (11)	0.0236 (10)	−0.0050 (10)	0.0014 (10)	0.0013 (9)
C6	0.0282 (10)	0.0270 (11)	0.0276 (10)	−0.0031 (10)	0.0000 (9)	−0.0030 (9)
C7	0.0285 (11)	0.0286 (12)	0.0334 (12)	−0.0054 (10)	−0.0020 (9)	0.0032 (10)
C8	0.0262 (11)	0.0284 (12)	0.0393 (13)	−0.0005 (10)	−0.0021 (10)	0.0054 (10)
C9	0.0349 (12)	0.0233 (11)	0.0266 (11)	−0.0002 (10)	−0.0020 (9)	0.0003 (9)
C10	0.0347 (12)	0.0259 (11)	0.0285 (11)	0.0016 (10)	0.0062 (10)	0.0010 (9)
C11	0.0308 (11)	0.0261 (11)	0.0291 (11)	−0.0023 (9)	0.0051 (9)	−0.0008 (9)
C12	0.0345 (12)	0.0316 (12)	0.0330 (11)	−0.0013 (11)	0.0057 (10)	0.0010 (10)
C13	0.0444 (15)	0.0340 (14)	0.071 (2)	0.0026 (13)	0.0060 (15)	−0.0162 (15)
B1	0.0261 (12)	0.0188 (11)	0.0258 (11)	0.0004 (10)	0.0020 (10)	−0.0009 (9)

O1—C7	1.417 (3)	C5—C6	1.392 (3)
O1—B1	1.449 (3)	C5—H5	0.9500
O2—C9	1.421 (3)	C6—H6	0.9500
O2—B1	1.474 (3)	C7—C8	1.525 (4)
O3—C12	1.333 (3)	C7—H7A	0.9900
O3—C13	1.455 (4)	C7—H7B	0.9900
O4—C12	1.193 (3)	C8—H8A	0.9900
N1—C10	1.488 (3)	C8—H8B	0.9900
N1—C8	1.491 (3)	C9—C10	1.523 (3)
N1—B1	1.681 (3)	C9—H9A	0.9900
N1—H1	0.9300	C9—H9B	0.9900
C1—C2	1.397 (3)	C10—H10A	0.9900
C1—C6	1.405 (3)	C10—H10B	0.9900
C1—B1	1.607 (3)	C11—C12	1.502 (3)
C2—C3	1.400 (3)	C11—H11A	0.9900
C2—H2	0.9500	C11—H11B	0.9900
C3—C4	1.391 (3)	C13—H13A	0.9800
C3—H3	0.9500	C13—H13B	0.9800
C4—C5	1.388 (3)	C13—H13C	0.9800
C4—C11	1.520 (3)
C7—O1—B1	109.67 (18)	N1—C8—H8B	111.1
C9—O2—B1	110.55 (17)	C7—C8—H8B	111.1
C12—O3—C13	114.9 (2)	H8A—C8—H8B	109.1
C10—N1—C8	114.44 (19)	O2—C9—C10	105.45 (19)
C10—N1—B1	105.44 (17)	O2—C9—H9A	110.7
C8—N1—B1	103.17 (17)	C10—C9—H9A	110.7
C10—N1—H1	111.1	O2—C9—H9B	110.7
C8—N1—H1	111.1	C10—C9—H9B	110.7
B1—N1—H1	111.1	H9A—C9—H9B	108.8
C2—C1—C6	116.5 (2)	N1—C10—C9	104.23 (19)
C2—C1—B1	123.6 (2)	N1—C10—H10A	110.9
C6—C1—B1	119.9 (2)	C9—C10—H10A	110.9
C1—C2—C3	121.8 (2)	N1—C10—H10B	110.9
C1—C2—H2	119.1	C9—C10—H10B	110.9
C3—C2—H2	119.1	H10A—C10—H10B	108.9
C4—C3—C2	120.7 (2)	C12—C11—C4	110.81 (19)
C4—C3—H3	119.7	C12—C11—H11A	109.5
C2—C3—H3	119.7	C4—C11—H11A	109.5
C5—C4—C3	118.2 (2)	C12—C11—H11B	109.5
C5—C4—C11	120.3 (2)	C4—C11—H11B	109.5
C3—C4—C11	121.5 (2)	H11A—C11—H11B	108.1
C4—C5—C6	121.0 (2)	O4—C12—O3	123.2 (3)
C4—C5—H5	119.5	O4—C12—C11	124.8 (3)
C6—C5—H5	119.5	O3—C12—C11	112.0 (2)
C5—C6—C1	121.7 (2)	O3—C13—H13A	109.5
C5—C6—H6	119.1	O3—C13—H13B	109.5
C1—C6—H6	119.1	H13A—C13—H13B	109.5
O1—C7—C8	104.28 (19)	O3—C13—H13C	109.5
O1—C7—H7A	110.9	H13A—C13—H13C	109.5
C8—C7—H7A	110.9	H13B—C13—H13C	109.5
O1—C7—H7B	110.9	O1—B1—O2	112.28 (19)
C8—C7—H7B	110.9	O1—B1—C1	111.41 (18)
H7A—C7—H7B	108.9	O2—B1—C1	116.1 (2)
N1—C8—C7	103.34 (19)	O1—B1—N1	101.97 (18)
N1—C8—H8A	111.1	O2—B1—N1	100.39 (17)
C7—C8—H8A	111.1	C1—B1—N1	113.35 (18)

Cg3 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.93	2.06	2.921 (2)	154
C10—H10B···Cg3ii	0.99	2.65	3.618 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.93	2.06	2.921 (2)	154
C10—H10B⋯Cg3ii	0.99	2.65	3.618 (2)	166

Symmetry codes: (i) ; (ii) .