3-(Dihy-droxy-bor-yl)anilinium 6-carb-oxy-pyridine-2-carboxyl-ate.

In the anion of the title molecular salt, C(6)H(9)BNO(2) (+)·C(7)H(4)NO(4) (-), the dihedral angles between the -COO(2-) and -CO(2)H groups and their attached ring are 4.02 (13) and 21.41 (10)°, respectively. The B atom in the cation adopts a syn-syn geometry and the dihedral angle between the -B(OH)(2) group and its attached ring is 11.06 (5)°. In the crystal, O-H⋯O, N-H⋯O and N-H⋯N hydrogen bonds link the components into a three-dimensional network.

Related literature

For general background, see: Hall (2005 ▶). For related structures, see: Li et al. (1995 ▶); SeethaLekshmi & Pedireddi (2006 ▶); Sokolov & MacGillivray (2006 ▶); Vega et al. (2010 ▶).

Experimental

Crystal data

C6H9BNO2 +·C7H4NO4 −

M = 304.06

Monoclinic,

a = 7.7065 (6) Å

b = 14.0473 (10) Å

c = 13.0852 (10) Å

β = 106.963 (1)°

V = 1354.92 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.28 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.958, T max = 0.989

8330 measured reflections

2677 independent reflections

2260 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.05

2677 reflections

206 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: Mercury (Macrae et al., 2006 ▶), PLATON (Spek, 2009 ▶), SHELXL97 and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812031790/cv5313sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031790/cv5313Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031790/cv5313Isup3.cml

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

C6H9BNO2+·C7H4NO4−	F(000) = 632
Mr = 304.06	Dx = 1.491 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 58 reflections
a = 7.7065 (6) Å	θ = 2.3–22.7°
b = 14.0473 (10) Å	µ = 0.12 mm−1
c = 13.0852 (10) Å	T = 293 K
β = 106.963 (1)°	Block, colourless
V = 1354.92 (18) Å3	0.28 × 0.25 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2677 independent reflections
Radiation source: fine-focus sealed tube	2260 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→8
Tmin = 0.958, Tmax = 0.989	k = −17→17
8330 measured reflections	l = −16→13

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.416P] where P = (Fo2 + 2Fc2)/3
2677 reflections	(Δ/σ)max < 0.001
206 parameters	Δρmax = 0.25 e Å−3
1 restraint	Δρmin = −0.20 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.

	x	y	z	Uiso*/Ueq
O2	0.99515 (15)	0.89532 (8)	0.27933 (8)	0.0301 (3)
B1	0.1026 (2)	0.91402 (12)	−0.06619 (13)	0.0257 (4)
C1	1.19186 (19)	0.93213 (10)	0.45205 (11)	0.0227 (3)
C2	1.1728 (2)	1.02978 (11)	0.43673 (12)	0.0300 (4)
H2	1.0986	1.0544	0.3729	0.036*
C3	1.2659 (2)	1.08965 (11)	0.51780 (14)	0.0363 (4)
H3	1.2534	1.1553	0.5101	0.044*
C4	1.3776 (2)	1.05063 (11)	0.61038 (13)	0.0319 (4)
H4	1.4459	1.0894	0.6650	0.038*
C5	1.38602 (19)	0.95208 (10)	0.62036 (12)	0.0248 (3)
C6	1.5061 (2)	0.90725 (10)	0.72088 (12)	0.0266 (3)
C7	1.09722 (19)	0.86419 (10)	0.36402 (11)	0.0233 (3)
C8	0.57150 (19)	0.81556 (10)	0.09336 (11)	0.0212 (3)
C9	0.5358 (2)	0.76762 (10)	0.17760 (12)	0.0246 (3)
H9	0.6274	0.7350	0.2274	0.030*
C10	0.3611 (2)	0.76933 (11)	0.18593 (12)	0.0280 (3)
H10	0.3345	0.7388	0.2426	0.034*
C11	0.2256 (2)	0.81672 (11)	0.10949 (12)	0.0273 (3)
H11	0.1085	0.8168	0.1157	0.033*
C12	0.2593 (2)	0.86417 (10)	0.02364 (12)	0.0241 (3)
C13	0.43773 (19)	0.86366 (10)	0.01759 (11)	0.0230 (3)
H13	0.4662	0.8958	−0.0376	0.028*
H1A	1.070 (4)	0.7337 (19)	0.329 (2)	0.103 (10)*
N1	1.29358 (16)	0.89300 (8)	0.54318 (9)	0.0222 (3)
N2	0.75722 (16)	0.81145 (8)	0.08587 (10)	0.0230 (3)
H2A	0.7832	0.7520	0.0719	0.034*
H2B	0.8341	0.8302	0.1475	0.034*
H2C	0.7673	0.8497	0.0337	0.034*
O1	1.13249 (15)	0.77632 (8)	0.38493 (8)	0.0309 (3)
O3	1.46409 (15)	0.82127 (8)	0.73569 (9)	0.0334 (3)
O4	1.63185 (16)	0.95337 (9)	0.77863 (10)	0.0424 (3)
O5	0.15502 (15)	0.96244 (9)	−0.14174 (9)	0.0371 (3)
H5	0.0661	0.9872	−0.1837	0.056*
O6	−0.07164 (14)	0.90249 (8)	−0.06323 (8)	0.0312 (3)
H6	−0.1416	0.9245	−0.1178	0.047*

	U11	U22	U33	U12	U13	U23
O2	0.0322 (6)	0.0294 (6)	0.0216 (5)	0.0028 (4)	−0.0035 (5)	0.0030 (4)
B1	0.0264 (9)	0.0232 (8)	0.0244 (9)	0.0018 (7)	0.0023 (7)	−0.0019 (6)
C1	0.0208 (7)	0.0259 (7)	0.0204 (7)	−0.0005 (6)	0.0045 (6)	0.0007 (6)
C2	0.0350 (9)	0.0271 (8)	0.0235 (8)	0.0021 (6)	0.0016 (7)	0.0039 (6)
C3	0.0485 (10)	0.0207 (7)	0.0351 (9)	0.0004 (7)	0.0050 (8)	0.0015 (7)
C4	0.0376 (9)	0.0249 (8)	0.0277 (8)	−0.0041 (7)	0.0008 (7)	−0.0043 (6)
C5	0.0222 (7)	0.0256 (7)	0.0242 (8)	−0.0002 (6)	0.0030 (6)	−0.0014 (6)
C6	0.0263 (8)	0.0265 (8)	0.0231 (8)	0.0017 (6)	0.0014 (6)	−0.0030 (6)
C7	0.0227 (7)	0.0261 (7)	0.0203 (7)	0.0012 (6)	0.0050 (6)	0.0022 (6)
C8	0.0190 (7)	0.0210 (7)	0.0220 (7)	−0.0012 (5)	0.0033 (5)	−0.0029 (5)
C9	0.0237 (7)	0.0250 (7)	0.0216 (7)	0.0014 (6)	0.0012 (6)	0.0013 (6)
C10	0.0287 (8)	0.0318 (8)	0.0237 (8)	−0.0001 (6)	0.0080 (6)	0.0043 (6)
C11	0.0201 (7)	0.0328 (8)	0.0290 (8)	0.0016 (6)	0.0071 (6)	−0.0001 (6)
C12	0.0237 (8)	0.0217 (7)	0.0245 (8)	0.0009 (6)	0.0033 (6)	−0.0025 (6)
C13	0.0247 (8)	0.0225 (7)	0.0208 (7)	−0.0001 (6)	0.0051 (6)	0.0013 (5)
N1	0.0193 (6)	0.0241 (6)	0.0209 (6)	−0.0004 (5)	0.0024 (5)	−0.0007 (5)
N2	0.0203 (6)	0.0241 (6)	0.0223 (6)	0.0000 (5)	0.0026 (5)	−0.0001 (5)
O1	0.0382 (7)	0.0241 (5)	0.0228 (6)	0.0001 (5)	−0.0031 (5)	0.0002 (4)
O3	0.0369 (7)	0.0280 (6)	0.0261 (6)	−0.0019 (5)	−0.0052 (5)	0.0029 (4)
O4	0.0396 (7)	0.0342 (6)	0.0369 (7)	−0.0055 (5)	−0.0145 (5)	−0.0009 (5)
O5	0.0291 (6)	0.0446 (7)	0.0344 (7)	0.0090 (5)	0.0042 (5)	0.0160 (5)
O6	0.0234 (6)	0.0377 (6)	0.0270 (6)	0.0021 (5)	−0.0010 (4)	0.0063 (5)

O2—C7	1.2367 (17)	C8—C13	1.381 (2)
B1—O5	1.355 (2)	C8—C9	1.386 (2)
B1—O6	1.365 (2)	C8—N2	1.4640 (18)
B1—C12	1.582 (2)	C9—C10	1.382 (2)
C1—N1	1.3391 (18)	C9—H9	0.9300
C1—C2	1.388 (2)	C10—C11	1.387 (2)
C1—C7	1.510 (2)	C10—H10	0.9300
C2—C3	1.380 (2)	C11—C12	1.394 (2)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.379 (2)	C12—C13	1.400 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.390 (2)	N2—H2A	0.8900
C4—H4	0.9300	N2—H2B	0.8900
C5—N1	1.3403 (19)	N2—H2C	0.8900
C5—C6	1.507 (2)	O1—H1A	0.963 (18)
C6—O4	1.2260 (19)	O5—H5	0.8200
C6—O3	1.2796 (19)	O6—H6	0.8200
C7—O1	1.2763 (18)
O5—B1—O6	125.84 (14)	C9—C8—N2	117.31 (12)
O5—B1—C12	116.05 (14)	C10—C9—C8	118.56 (14)
O6—B1—C12	118.08 (13)	C10—C9—H9	120.7
N1—C1—C2	122.97 (13)	C8—C9—H9	120.7
N1—C1—C7	116.54 (12)	C9—C10—C11	119.81 (14)
C2—C1—C7	120.48 (13)	C9—C10—H10	120.1
C3—C2—C1	118.82 (14)	C11—C10—H10	120.1
C3—C2—H2	120.6	C10—C11—C12	122.15 (14)
C1—C2—H2	120.6	C10—C11—H11	118.9
C4—C3—C2	118.99 (14)	C12—C11—H11	118.9
C4—C3—H3	120.5	C11—C12—C13	117.39 (13)
C2—C3—H3	120.5	C11—C12—B1	121.94 (13)
C3—C4—C5	118.59 (14)	C13—C12—B1	120.64 (13)
C3—C4—H4	120.7	C8—C13—C12	120.12 (13)
C5—C4—H4	120.7	C8—C13—H13	119.9
N1—C5—C4	123.08 (14)	C12—C13—H13	119.9
N1—C5—C6	117.05 (13)	C1—N1—C5	117.46 (12)
C4—C5—C6	119.86 (13)	C8—N2—H2A	109.5
O4—C6—O3	126.49 (14)	C8—N2—H2B	109.5
O4—C6—C5	119.39 (14)	H2A—N2—H2B	109.5
O3—C6—C5	114.12 (13)	C8—N2—H2C	109.5
O2—C7—O1	125.03 (14)	H2A—N2—H2C	109.5
O2—C7—C1	119.97 (13)	H2B—N2—H2C	109.5
O1—C7—C1	114.99 (12)	C7—O1—H1A	114.1 (18)
C13—C8—C9	121.94 (13)	B1—O5—H5	109.5
C13—C8—N2	120.73 (13)	B1—O6—H6	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3i	0.96 (2)	1.47 (3)	2.429 (2)	173 (2)
N2—H2A···O1i	0.89	2.42	2.808 (2)	107
N2—H2A···O3i	0.89	2.42	2.835 (2)	109
N2—H2A···N1i	0.89	2.08	2.955 (2)	169
N2—H2B···O3i	0.89	2.49	2.835 (2)	104
N2—H2B···O2	0.89	2.03	2.907 (2)	170
N2—H2C···O6ii	0.89	2.15	2.947 (2)	149
O5—H5···O2iii	0.82	2.04	2.712 (2)	139
O6—H6···O4iv	0.82	1.91	2.694 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3i	0.96 (2)	1.47 (3)	2.429 (2)	173 (2)
N2—H2A⋯O1i	0.89	2.42	2.808 (2)	107
N2—H2A⋯O3i	0.89	2.42	2.835 (2)	109
N2—H2A⋯N1i	0.89	2.08	2.955 (2)	169
N2—H2B⋯O3i	0.89	2.49	2.835 (2)	104
N2—H2B⋯O2	0.89	2.03	2.907 (2)	170
N2—H2C⋯O6ii	0.89	2.15	2.947 (2)	149
O5—H5⋯O2iii	0.82	2.04	2.712 (2)	139
O6—H6⋯O4iv	0.82	1.91	2.694 (2)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .