1,3-Dimethyl 5-(4,4,5,5-tetra-methyl-1,3,2-dioxaborolan-2-yl)benzene-1,3-dicarboxyl-ate.

The title compound, C(16)H(21)BO(6), has has approximate C(2) symmetry, but no crystallographically imposed mol-ecular symmetry. In the crystal, mol-ecules are packed into parallel columns along the a axis. Short inter-molecular C-H⋯O contacts stabilize the crystal packing.

Related literature

For the synthesis of organoboronic esters, see: Kikuchi et al. (2008 ▶). For the synthesis of the title compound, see: Coventry et al. (2005 ▶).

Experimental

Crystal data

C16H21BO6

M = 320.14

Orthorhombic,

a = 7.2163 (2) Å

b = 20.9627 (4) Å

c = 22.4624 (4) Å

V = 3397.96 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

1.00 × 0.40 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.766, T max = 0.982

22413 measured reflections

3864 independent reflections

2177 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.142

S = 1.01

3864 reflections

215 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054559/bt5730sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054559/bt5730Isup4.hkl

Supplementary material file. DOI: 10.1107/S1600536811054559/bt5730Isup3.cml

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

C16H21BO6	F(000) = 1360
Mr = 320.14	Dx = 1.252 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3703 reflections
a = 7.2163 (2) Å	θ = 2.7–20.6°
b = 20.9627 (4) Å	µ = 0.09 mm−1
c = 22.4624 (4) Å	T = 296 K
V = 3397.96 (13) Å3	Pod, colourless
Z = 8	1.00 × 0.40 × 0.20 mm

Bruker APEXII CCD diffractometer	3864 independent reflections
Radiation source: fine-focus sealed tube	2177 reflections with I > 2σ(I)
graphite	Rint = 0.043
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.766, Tmax = 0.982	k = −27→26
22413 measured reflections	l = −27→29

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0653P)2 + 0.3179P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3864 reflections	Δρmax = 0.18 e Å−3
215 parameters	Δρmin = −0.14 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: 0.0031 (5)

Experimental. SADABS (Bruker, 2005) was used for absorption correction. R(int) was 0.0776 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.9190. The λ/2 correction factor is Not present.

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
O1	0.67152 (17)	0.13558 (5)	0.42187 (5)	0.0525 (4)
O2	0.6570 (2)	0.16197 (6)	0.20099 (6)	0.0739 (5)
O3	0.74902 (17)	0.03889 (5)	0.46030 (5)	0.0484 (3)
O4	0.6855 (2)	0.08265 (7)	0.13639 (6)	0.0817 (5)
O5	0.8187 (2)	−0.14641 (6)	0.32004 (7)	0.0785 (5)
O6	0.8121 (3)	−0.13786 (7)	0.22123 (7)	0.0903 (6)
C1	0.4427 (3)	0.13373 (9)	0.49842 (10)	0.0679 (6)
H1A	0.3750	0.1642	0.4751	0.102*
H1B	0.4192	0.1411	0.5399	0.102*
H1C	0.4037	0.0914	0.4880	0.102*
C2	0.6479 (2)	0.14086 (7)	0.48620 (8)	0.0439 (4)
C3	0.7180 (2)	0.04498 (8)	0.34685 (7)	0.0452 (4)
C4	0.6938 (2)	0.08372 (9)	0.29731 (8)	0.0474 (4)
H4	0.6698	0.1269	0.3028	0.057*
C5	0.7043 (2)	0.05958 (8)	0.23990 (8)	0.0462 (4)
C6	0.6823 (3)	0.10082 (9)	0.18671 (9)	0.0546 (5)
C7	0.6358 (4)	0.20504 (11)	0.15139 (9)	0.0952 (9)
H7A	0.7436	0.2027	0.1264	0.143*
H7B	0.6216	0.2478	0.1659	0.143*
H7C	0.5282	0.1933	0.1288	0.143*
C8	0.9702 (3)	0.10025 (10)	0.51525 (9)	0.0702 (6)
H8A	1.0391	0.0619	0.5225	0.105*
H8B	0.9880	0.1293	0.5478	0.105*
H8C	1.0128	0.1197	0.4790	0.105*
C9	0.7647 (3)	0.08423 (8)	0.50955 (7)	0.0461 (4)
C10	0.7157 (3)	0.20608 (8)	0.50516 (9)	0.0651 (6)
H10A	0.8413	0.2118	0.4922	0.098*
H10B	0.7102	0.2094	0.5477	0.098*
H10C	0.6386	0.2383	0.4876	0.098*
C11	0.7376 (3)	−0.00497 (9)	0.23160 (8)	0.0515 (5)
H11	0.7437	−0.0216	0.1933	0.062*
C12	0.7619 (2)	−0.04497 (8)	0.28033 (8)	0.0481 (5)
C13	0.7995 (3)	−0.11372 (10)	0.26942 (10)	0.0621 (6)
C14	0.8615 (5)	−0.21352 (10)	0.31398 (12)	0.1040 (9)
H14A	0.7605	−0.2348	0.2945	0.156*
H14B	0.8803	−0.2318	0.3527	0.156*
H14C	0.9721	−0.2184	0.2907	0.156*
C15	0.7531 (2)	−0.01959 (8)	0.33725 (8)	0.0488 (5)
H15	0.7709	−0.0463	0.3698	0.059*
C16	0.6931 (4)	0.05342 (10)	0.56561 (9)	0.0764 (7)
H16A	0.5692	0.0383	0.5591	0.115*
H16B	0.6928	0.0841	0.5973	0.115*
H16C	0.7717	0.0182	0.5761	0.115*
B1	0.7131 (3)	0.07327 (9)	0.41089 (9)	0.0421 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0751 (9)	0.0423 (7)	0.0400 (7)	0.0040 (6)	−0.0016 (6)	−0.0003 (5)
O2	0.1243 (13)	0.0555 (9)	0.0418 (8)	−0.0010 (8)	−0.0037 (8)	0.0037 (6)
O3	0.0700 (9)	0.0377 (6)	0.0375 (7)	0.0065 (5)	−0.0026 (6)	−0.0054 (5)
O4	0.1359 (14)	0.0728 (10)	0.0364 (8)	0.0053 (9)	0.0016 (8)	−0.0029 (7)
O5	0.1204 (13)	0.0542 (9)	0.0610 (10)	0.0147 (8)	0.0004 (9)	−0.0028 (7)
O6	0.1523 (17)	0.0612 (9)	0.0573 (10)	0.0077 (9)	0.0085 (10)	−0.0174 (7)
C1	0.0513 (12)	0.0673 (13)	0.0853 (16)	0.0041 (10)	0.0048 (11)	−0.0188 (11)
C2	0.0520 (11)	0.0382 (9)	0.0417 (10)	0.0004 (7)	0.0012 (8)	−0.0070 (7)
C3	0.0483 (10)	0.0526 (10)	0.0349 (10)	−0.0010 (8)	0.0002 (8)	−0.0016 (8)
C4	0.0514 (11)	0.0490 (10)	0.0419 (10)	−0.0024 (8)	0.0019 (8)	−0.0032 (8)
C5	0.0492 (11)	0.0538 (11)	0.0357 (10)	−0.0045 (8)	0.0019 (8)	−0.0023 (8)
C6	0.0643 (13)	0.0580 (12)	0.0415 (12)	−0.0046 (9)	0.0020 (9)	−0.0024 (9)
C7	0.165 (3)	0.0633 (14)	0.0578 (15)	0.0008 (15)	−0.0084 (15)	0.0172 (12)
C8	0.0604 (14)	0.0768 (14)	0.0736 (15)	0.0113 (10)	−0.0213 (11)	−0.0182 (11)
C9	0.0623 (12)	0.0421 (9)	0.0337 (10)	0.0029 (8)	−0.0058 (8)	−0.0074 (7)
C10	0.0740 (14)	0.0416 (10)	0.0797 (16)	−0.0033 (9)	−0.0017 (11)	−0.0137 (10)
C11	0.0601 (12)	0.0596 (11)	0.0349 (10)	−0.0051 (9)	0.0023 (8)	−0.0088 (9)
C12	0.0517 (11)	0.0502 (10)	0.0424 (11)	−0.0024 (8)	0.0007 (8)	−0.0064 (8)
C13	0.0777 (15)	0.0574 (12)	0.0514 (13)	−0.0001 (10)	0.0035 (11)	−0.0059 (10)
C14	0.163 (3)	0.0530 (14)	0.096 (2)	0.0214 (15)	0.0036 (18)	0.0028 (13)
C15	0.0546 (11)	0.0509 (11)	0.0410 (10)	−0.0012 (8)	0.0001 (8)	−0.0019 (8)
C16	0.128 (2)	0.0618 (13)	0.0393 (12)	0.0006 (12)	0.0063 (12)	0.0024 (10)
B1	0.0470 (11)	0.0404 (10)	0.0390 (12)	−0.0019 (8)	−0.0001 (9)	0.0004 (9)

O1—B1	1.363 (2)	C7—H7A	0.9600
O1—C2	1.459 (2)	C7—H7B	0.9600
O2—C6	1.334 (2)	C7—H7C	0.9600
O2—C7	1.442 (2)	C8—C9	1.526 (3)
O3—B1	1.349 (2)	C8—H8A	0.9600
O3—C9	1.4629 (19)	C8—H8B	0.9600
O4—C6	1.193 (2)	C8—H8C	0.9600
O5—C13	1.335 (2)	C9—C16	1.506 (3)
O5—C14	1.447 (2)	C10—H10A	0.9600
O6—C13	1.198 (2)	C10—H10B	0.9600
C1—C2	1.514 (3)	C10—H10C	0.9600
C1—H1A	0.9600	C11—C12	1.390 (2)
C1—H1B	0.9600	C11—H11	0.9300
C1—H1C	0.9600	C12—C15	1.386 (2)
C2—C10	1.513 (2)	C12—C13	1.487 (3)
C2—C9	1.547 (2)	C14—H14A	0.9600
C3—C4	1.389 (2)	C14—H14B	0.9600
C3—C15	1.394 (2)	C14—H14C	0.9600
C3—B1	1.556 (2)	C15—H15	0.9300
C4—C5	1.387 (2)	C16—H16A	0.9600
C4—H4	0.9300	C16—H16B	0.9600
C5—C11	1.387 (3)	C16—H16C	0.9600
C5—C6	1.483 (3)
B1—O1—C2	106.12 (12)	O3—C9—C16	109.10 (14)
C6—O2—C7	115.49 (16)	O3—C9—C8	106.34 (14)
B1—O3—C9	106.86 (13)	C16—C9—C8	110.94 (17)
C13—O5—C14	116.17 (17)	O3—C9—C2	101.54 (12)
C2—C1—H1A	109.5	C16—C9—C2	115.20 (16)
C2—C1—H1B	109.5	C8—C9—C2	112.88 (15)
H1A—C1—H1B	109.5	C2—C10—H10A	109.5
C2—C1—H1C	109.5	C2—C10—H10B	109.5
H1A—C1—H1C	109.5	H10A—C10—H10B	109.5
H1B—C1—H1C	109.5	C2—C10—H10C	109.5
O1—C2—C10	108.03 (14)	H10A—C10—H10C	109.5
O1—C2—C1	106.63 (14)	H10B—C10—H10C	109.5
C10—C2—C1	110.76 (15)	C5—C11—C12	120.31 (16)
O1—C2—C9	102.36 (12)	C5—C11—H11	119.8
C10—C2—C9	114.95 (15)	C12—C11—H11	119.8
C1—C2—C9	113.30 (15)	C15—C12—C11	119.27 (17)
C4—C3—C15	117.82 (16)	C15—C12—C13	122.17 (17)
C4—C3—B1	121.00 (16)	C11—C12—C13	118.56 (17)
C15—C3—B1	121.15 (16)	O6—C13—O5	123.02 (19)
C5—C4—C3	121.65 (17)	O6—C13—C12	124.89 (19)
C5—C4—H4	119.2	O5—C13—C12	112.09 (17)
C3—C4—H4	119.2	O5—C14—H14A	109.5
C11—C5—C4	119.35 (16)	O5—C14—H14B	109.5
C11—C5—C6	118.62 (16)	H14A—C14—H14B	109.5
C4—C5—C6	122.02 (16)	O5—C14—H14C	109.5
O4—C6—O2	122.50 (18)	H14A—C14—H14C	109.5
O4—C6—C5	125.10 (18)	H14B—C14—H14C	109.5
O2—C6—C5	112.40 (16)	C12—C15—C3	121.59 (17)
O2—C7—H7A	109.5	C12—C15—H15	119.2
O2—C7—H7B	109.5	C3—C15—H15	119.2
H7A—C7—H7B	109.5	C9—C16—H16A	109.5
O2—C7—H7C	109.5	C9—C16—H16B	109.5
H7A—C7—H7C	109.5	H16A—C16—H16B	109.5
H7B—C7—H7C	109.5	C9—C16—H16C	109.5
C9—C8—H8A	109.5	H16A—C16—H16C	109.5
C9—C8—H8B	109.5	H16B—C16—H16C	109.5
H8A—C8—H8B	109.5	O3—B1—O1	113.93 (15)
C9—C8—H8C	109.5	O3—B1—C3	123.55 (16)
H8A—C8—H8C	109.5	O1—B1—C3	122.52 (16)
H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16C···O4i	0.96	2.53	3.381 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16C⋯O4i	0.96	2.53	3.381 (3)	148

Symmetry code: (i) .