tert-Butyl 2-(dihydroxyboryl)pyrrole-1-carboxylate.

In the title compound, C(9)H(14)BNO(4), the carbonyl and boronic acid groups are essentially coplanar with the pyrrole ring and the boronic acid group has an exo-endo conformation. The exo-oriented OH is engaged in an intra-molecular O-H⋯O inter-action, while the endo-oriented one is involved in inter-molecular hydrogen bonding to form centrosymmetric dimers. A supra-molecular assembly is achieved through inter-actions involving the tert-butyl groups, forming infinite chains along the crystallographic b axis. There are, in addition, face-to-face and center-to-edge stacking inter-actions [distance between the pyrrole ring centroid and an N atom from a neighbouring mol-ecule = 3.369 (8) Å].

Related literature

For related literature, see: Dabrowski et al. (2006 ▶); Parry et al. (2002 ▶); Saygili et al. (2004 ▶); Seminario et al. (1998 ▶); Thompson et al. (2005 ▶); Wang et al. (2002 ▶).

Experimental

Crystal data

C9H14BNO4

M = 211.02

Orthorhombic,

a = 12.9179 (12) Å

b = 9.5885 (7) Å

c = 17.5811 (15) Å

V = 2177.7 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 (2) K

0.71 × 0.34 × 0.22 mm

Data collection

Kuma KM4 CCD diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction 2005 ▶) T min = 0.95, T max = 0.98

19290 measured reflections

2713 independent reflections

1911 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.076

S = 0.96

2713 reflections

193 parameters

All H-atom parameters refined

Δρmax = 0.26 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808013482/bg2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013482/bg2173Isup2.hkl

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

C9H14BNO4	F000 = 896
Mr = 211.02	Dx = 1.287 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 19290 reflections
a = 12.9179 (12) Å	θ = 2.8–28.7º
b = 9.5885 (7) Å	µ = 0.10 mm−1
c = 17.5811 (15) Å	T = 100 (2) K
V = 2177.7 (3) Å3	Prismatic, colourless
Z = 8	0.71 × 0.34 × 0.22 mm

Kuma KM4 CCD diffractometer	2713 independent reflections
Radiation source: fine-focus sealed tube	1911 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
Detector resolution: 8.6479 pixels mm-1	θmax = 28.7º
T = 100(2) K	θmin = 2.8º
ω scan	h = −17→17
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction 2005)	k = −12→12
Tmin = 0.95, Tmax = 0.98	l = −23→23
19290 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	All H-atom parameters refined
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.0461P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076	(Δ/σ)max = 0.001
S = 0.97	Δρmax = 0.26 e Å−3
2713 reflections	Δρmin = −0.19 e Å−3
193 parameters	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (7)
Secondary atom site location: difference Fourier map

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	0.54350 (6)	0.63771 (7)	0.45212 (4)	0.02586 (19)
O2	0.40336 (6)	0.64180 (8)	0.53731 (4)	0.02619 (19)
O3	0.60617 (5)	0.83554 (7)	0.36263 (4)	0.02260 (18)
O4	0.56150 (5)	1.04637 (7)	0.31656 (4)	0.02186 (18)
N1	0.46192 (6)	0.95162 (8)	0.40642 (4)	0.01800 (19)
C1	0.42176 (8)	0.85423 (10)	0.45945 (5)	0.0187 (2)
C2	0.33504 (8)	0.91604 (11)	0.48868 (6)	0.0223 (2)
C3	0.32126 (8)	1.05007 (11)	0.45569 (6)	0.0242 (2)
C4	0.39900 (8)	1.06957 (10)	0.40571 (6)	0.0218 (2)
C5	0.54985 (8)	0.93691 (9)	0.36119 (5)	0.0186 (2)
C6	0.64575 (8)	1.04984 (10)	0.25803 (5)	0.0225 (2)
C7	0.63032 (10)	0.93008 (12)	0.20274 (6)	0.0285 (3)
C8	0.75028 (9)	1.04896 (12)	0.29709 (6)	0.0269 (2)
C9	0.62477 (10)	1.18889 (12)	0.22011 (7)	0.0304 (3)
B1	0.46066 (9)	0.70564 (12)	0.48297 (6)	0.0204 (2)
H1O	0.5763 (11)	0.6964 (15)	0.4187 (8)	0.056 (4)*
H2O	0.4234 (12)	0.5504 (17)	0.5442 (8)	0.060 (5)*
H2	0.2915 (8)	0.8741 (11)	0.5269 (5)	0.018 (2)*
H3	0.2680 (9)	1.1122 (12)	0.4668 (6)	0.028 (3)*
H4	0.4168 (8)	1.1463 (11)	0.3729 (6)	0.020 (3)*
H7A	0.5580 (11)	0.9321 (12)	0.1830 (7)	0.038 (3)*
H7B	0.6429 (9)	0.8387 (12)	0.2253 (6)	0.029 (3)*
H7C	0.6788 (9)	0.9424 (11)	0.1603 (6)	0.029 (3)*
H8A	0.7576 (9)	1.1342 (13)	0.3317 (7)	0.038 (3)*
H8B	0.7629 (9)	0.9613 (12)	0.3252 (6)	0.031 (3)*
H8C	0.8046 (10)	1.0547 (12)	0.2579 (7)	0.036 (3)*
H9A	0.6288 (8)	1.2649 (12)	0.2567 (7)	0.034 (3)*
H9B	0.5551 (10)	1.1878 (13)	0.1981 (6)	0.040 (3)*
H9C	0.6768 (9)	1.2037 (12)	0.1802 (7)	0.039 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0238 (4)	0.0218 (4)	0.0320 (4)	0.0014 (3)	0.0056 (3)	0.0085 (3)
O2	0.0255 (4)	0.0253 (4)	0.0278 (4)	−0.0001 (3)	0.0051 (3)	0.0059 (3)
O3	0.0227 (4)	0.0186 (4)	0.0265 (4)	0.0021 (3)	0.0044 (3)	0.0032 (3)
O4	0.0240 (4)	0.0180 (4)	0.0235 (4)	0.0007 (3)	0.0031 (3)	0.0038 (3)
N1	0.0172 (4)	0.0178 (4)	0.0190 (4)	0.0001 (3)	−0.0011 (3)	−0.0005 (3)
C1	0.0181 (5)	0.0220 (5)	0.0159 (4)	−0.0040 (4)	−0.0023 (4)	−0.0013 (4)
C2	0.0188 (5)	0.0286 (6)	0.0194 (5)	−0.0018 (4)	−0.0009 (4)	−0.0039 (4)
C3	0.0195 (5)	0.0264 (6)	0.0267 (5)	0.0049 (5)	−0.0040 (4)	−0.0071 (4)
C4	0.0220 (5)	0.0194 (5)	0.0239 (5)	0.0029 (4)	−0.0061 (4)	−0.0022 (4)
C5	0.0203 (5)	0.0170 (5)	0.0186 (5)	−0.0027 (4)	−0.0026 (4)	−0.0011 (4)
C6	0.0245 (6)	0.0228 (5)	0.0203 (5)	−0.0023 (4)	0.0036 (4)	0.0031 (4)
C7	0.0341 (7)	0.0281 (6)	0.0233 (6)	−0.0037 (5)	0.0027 (5)	−0.0002 (4)
C8	0.0258 (6)	0.0270 (6)	0.0278 (6)	−0.0045 (5)	0.0011 (5)	0.0047 (5)
C9	0.0339 (7)	0.0270 (6)	0.0304 (6)	−0.0027 (5)	0.0012 (5)	0.0087 (5)
B1	0.0193 (6)	0.0230 (6)	0.0190 (5)	−0.0038 (5)	−0.0027 (5)	−0.0013 (5)

O1—B1	1.3652 (13)	C3—H3	0.931 (12)
O1—H1O	0.917 (15)	C4—H4	0.963 (10)
O2—B1	1.3547 (13)	C6—C8	1.5149 (15)
O2—H2O	0.922 (16)	C6—C9	1.5151 (14)
O3—C5	1.2143 (11)	C6—C7	1.5176 (14)
O4—C5	1.3191 (11)	C7—H7A	0.996 (13)
O4—C6	1.4981 (12)	C7—H7B	0.976 (11)
N1—C4	1.3928 (12)	C7—H7C	0.981 (12)
N1—C5	1.3937 (12)	C8—H8A	1.023 (13)
N1—C1	1.4178 (12)	C8—H8B	0.989 (12)
C1—C2	1.3676 (14)	C8—H8C	0.985 (13)
C1—B1	1.5665 (15)	C9—H9A	0.973 (12)
C2—C3	1.4211 (15)	C9—H9B	0.980 (13)
C2—H2	0.964 (10)	C9—H9C	0.983 (12)
C3—C4	1.3474 (15)
B1—O1—H1O	108.9 (9)	O4—C6—C7	109.13 (8)
B1—O2—H2O	111.6 (9)	C8—C6—C7	113.78 (9)
C5—O4—C6	120.61 (7)	C9—C6—C7	111.13 (9)
C4—N1—C5	123.55 (8)	C6—C7—H7A	109.4 (7)
C4—N1—C1	109.10 (8)	C6—C7—H7B	113.4 (6)
C5—N1—C1	127.35 (8)	H7A—C7—H7B	108.4 (10)
C2—C1—N1	105.15 (8)	C6—C7—H7C	108.2 (6)
C2—C1—B1	123.90 (9)	H7A—C7—H7C	109.3 (9)
N1—C1—B1	130.94 (9)	H7B—C7—H7C	108.1 (9)
C1—C2—C3	109.95 (9)	C6—C8—H8A	110.3 (7)
C1—C2—H2	124.0 (6)	C6—C8—H8B	112.2 (7)
C3—C2—H2	126.0 (6)	H8A—C8—H8B	111.5 (9)
C4—C3—C2	107.35 (9)	C6—C8—H8C	108.5 (7)
C4—C3—H3	126.8 (7)	H8A—C8—H8C	107.8 (9)
C2—C3—H3	125.9 (7)	H8B—C8—H8C	106.2 (9)
C3—C4—N1	108.44 (9)	C6—C9—H9A	111.0 (7)
C3—C4—H4	132.4 (6)	C6—C9—H9B	109.2 (7)
N1—C4—H4	119.1 (6)	H9A—C9—H9B	108.6 (10)
O3—C5—O4	125.51 (9)	C6—C9—H9C	108.6 (7)
O3—C5—N1	123.88 (8)	H9A—C9—H9C	109.1 (10)
O4—C5—N1	110.60 (8)	H9B—C9—H9C	110.4 (9)
O4—C6—C8	109.64 (8)	O2—B1—O1	119.54 (10)
O4—C6—C9	101.06 (8)	O2—B1—C1	114.96 (9)
C8—C6—C9	111.34 (9)	O1—B1—C1	125.49 (9)
C4—N1—C1—C2	0.54 (10)	C4—N1—C5—O3	178.49 (9)
C5—N1—C1—C2	−179.63 (8)	C1—N1—C5—O3	−1.32 (14)
C4—N1—C1—B1	179.79 (9)	C4—N1—C5—O4	−2.55 (12)
C5—N1—C1—B1	−0.38 (15)	C1—N1—C5—O4	177.64 (8)
N1—C1—C2—C3	−0.70 (10)	C5—O4—C6—C8	−64.93 (11)
B1—C1—C2—C3	179.99 (9)	C5—O4—C6—C9	177.47 (8)
C1—C2—C3—C4	0.62 (11)	C5—O4—C6—C7	60.31 (11)
C2—C3—C4—N1	−0.26 (11)	C2—C1—B1—O2	−1.97 (14)
C5—N1—C4—C3	179.99 (8)	N1—C1—B1—O2	178.91 (9)
C1—N1—C4—C3	−0.17 (10)	C2—C1—B1—O1	176.28 (10)
C6—O4—C5—O3	3.95 (14)	N1—C1—B1—O1	−2.85 (16)
C6—O4—C5—N1	−174.99 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O3	0.917 (15)	1.704 (15)	2.5941 (10)	162.9 (13)
O2—H2O···O1i	0.922 (16)	1.855 (17)	2.7728 (11)	173.7 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯O3	0.917 (15)	1.704 (15)	2.5941 (10)	162.9 (13)
O2—H2O⋯O1i	0.922 (16)	1.855 (17)	2.7728 (11)	173.7 (13)

Symmetry code: (i) .