Bis[(m-phenyl-enedimethyl-ene)-diammonium] tetra-deca-borate.

The title compound 2C(8)H(14)N(2) (2+)·[B(14)O(20)(OH)(6)](4-), contains diprotonated C(8)H(14)N(2) (2+) cations and centrosymmetric tetra-deca-borate anions. The crystal structure is stabilized by O-H⋯O and N-H⋯O hydrogen bonds.

Related literature

For background on the importance of borate compounds, see: Chen et al. (1995 ▶); Grice et al. (1999 ▶). For previous work on boron oxoanions, see: Liu et al. (2006 ▶); Pan et al. (2007 ▶); Grice et al. (1999 ▶); Schubert et al. (2000 ▶); Touboul et al. (2003 ▶); Burns (1995 ▶).

Experimental

Crystal data

2C8H14N2 2+·B14H6O26 4−

M = 849.81

Triclinic,

a = 9.1025 (18) Å

b = 10.293 (2) Å

c = 10.942 (2) Å

α = 109.68 (3)°

β = 108.24 (3)°

γ = 102.19 (3)°

V = 857.4 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.14 mm−1

T = 295 (2) K

0.34 × 0.26 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.964, T max = 0.973

6803 measured reflections

3009 independent reflections

2002 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.128

S = 1.24

3009 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.46 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808033333/bt2801sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033333/bt2801Isup2.hkl

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

2C8H14N22+·B14H6O264−	Z = 1
Mr = 849.81	F(000) = 436
Triclinic, P1	Dx = 1.646 Mg m−3
Hall symbol: -P1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1025 (18) Å	Cell parameters from 4940 reflections
b = 10.293 (2) Å	θ = 6.7–54.9°
c = 10.942 (2) Å	µ = 0.14 mm−1
α = 109.68 (3)°	T = 295 K
β = 108.24 (3)°	Block, colourless
γ = 102.19 (3)°	0.34 × 0.26 × 0.18 mm
V = 857.4 (5) Å3

Rigaku R-AXIS RAPID diffractometer	3009 independent reflections
Radiation source: fine-focus sealed tube	2002 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 25.0°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.964, Tmax = 0.973	k = −12→12
6803 measured reflections	l = −12→12

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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0299P)2 + 1.2547P] where P = (Fo2 + 2Fc2)/3
S = 1.24	(Δ/σ)max < 0.001
3009 reflections	Δρmax = 0.42 e Å−3
272 parameters	Δρmin = −0.46 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: 0.012 (2)

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
B1	0.6460 (5)	0.4668 (4)	0.7888 (4)	0.0240 (8)
B2	0.7413 (4)	0.3345 (4)	0.6060 (4)	0.0222 (8)
B3	0.5338 (4)	0.1936 (4)	0.6602 (4)	0.0247 (8)
B4	0.6535 (4)	0.6248 (4)	1.0187 (4)	0.0209 (7)
B5	0.4617 (5)	0.6104 (4)	0.8040 (4)	0.0233 (8)
B6	0.7437 (4)	0.3478 (4)	0.3829 (4)	0.0225 (8)
B7	0.9709 (5)	0.3173 (4)	0.5343 (4)	0.0252 (8)
O1	0.7649 (3)	0.4597 (2)	0.7304 (2)	0.0238 (5)
O2	0.6220 (3)	0.1961 (2)	0.5811 (2)	0.0279 (5)
O3	0.5410 (3)	0.3195 (2)	0.7601 (2)	0.0266 (5)
O4	0.7324 (3)	0.5555 (2)	0.9474 (2)	0.0231 (5)
O5	0.5160 (3)	0.6519 (2)	0.9489 (2)	0.0259 (5)
O6	0.5330 (3)	0.5377 (2)	0.7283 (2)	0.0248 (5)
O7	0.6718 (3)	0.3576 (2)	0.4736 (2)	0.0263 (5)
O8	0.8946 (3)	0.3301 (3)	0.4095 (2)	0.0297 (6)
O9	0.9009 (3)	0.3166 (2)	0.6244 (2)	0.0260 (5)
O10	0.4275 (3)	0.0652 (3)	0.6413 (3)	0.0447 (7)
H10A	0.4225	−0.0042	0.5733	0.067*
O11	0.7074 (3)	0.6690 (2)	1.1630 (2)	0.0269 (5)
H11A	0.6297	0.6722	1.1852	0.040*
O12	0.3292 (3)	0.6490 (3)	0.7475 (2)	0.0284 (5)
O13	1.1239 (3)	0.3064 (3)	0.5617 (2)	0.0374 (6)
H13A	1.1659	0.3147	0.6433	0.056*
N1	0.3291 (3)	0.3057 (3)	0.4112 (3)	0.0329 (7)
H1A	0.4353	0.3287	0.4654	0.049*
H1B	0.2747	0.3228	0.4662	0.049*
H1C	0.3203	0.3605	0.3633	0.049*
N2	−0.1153 (3)	0.4082 (3)	0.0950 (3)	0.0320 (7)
H2A	−0.1372	0.4667	0.0531	0.048*
H2B	−0.0078	0.4427	0.1513	0.048*
H2C	−0.1730	0.4060	0.1471	0.048*
C1	0.0788 (4)	0.1079 (4)	0.2176 (4)	0.0316 (8)
C2	0.0378 (4)	0.1765 (4)	0.1291 (4)	0.0313 (8)
H2D	0.1214	0.2350	0.1185	0.038*
C3	−0.1245 (4)	0.1600 (4)	0.0564 (4)	0.0310 (8)
C4	−0.2492 (4)	0.0650 (4)	0.0667 (4)	0.0380 (9)
H4A	−0.3593	0.0505	0.0165	0.046*
C5	−0.2107 (5)	−0.0074 (4)	0.1508 (4)	0.0452 (10)
H5A	−0.2949	−0.0713	0.1563	0.054*
C6	−0.0475 (5)	0.0143 (4)	0.2272 (4)	0.0387 (9)
H6A	−0.0220	−0.0337	0.2850	0.046*
C7	0.2573 (5)	0.1467 (4)	0.3083 (4)	0.0413 (9)
H7A	0.2681	0.0865	0.3600	0.050*
H7B	0.3166	0.1274	0.2483	0.050*
C8	−0.1624 (5)	0.2555 (4)	−0.0168 (4)	0.0373 (9)
H8A	−0.2794	0.2172	−0.0789	0.045*
H8B	−0.1006	0.2570	−0.0744	0.045*

	U11	U22	U33	U12	U13	U23
B1	0.0293 (19)	0.027 (2)	0.0191 (19)	0.0131 (16)	0.0134 (16)	0.0092 (16)
B2	0.0212 (18)	0.025 (2)	0.0231 (19)	0.0095 (15)	0.0124 (16)	0.0104 (16)
B3	0.0267 (19)	0.024 (2)	0.024 (2)	0.0084 (16)	0.0132 (16)	0.0098 (17)
B4	0.0219 (18)	0.0198 (18)	0.0207 (19)	0.0057 (14)	0.0104 (15)	0.0081 (15)
B5	0.0287 (19)	0.0248 (19)	0.0197 (19)	0.0128 (16)	0.0115 (16)	0.0101 (16)
B6	0.0245 (19)	0.0242 (19)	0.0179 (18)	0.0128 (15)	0.0081 (15)	0.0060 (15)
B7	0.0265 (19)	0.032 (2)	0.0162 (18)	0.0142 (17)	0.0085 (16)	0.0072 (16)
O1	0.0236 (11)	0.0247 (12)	0.0230 (12)	0.0071 (9)	0.0145 (10)	0.0067 (10)
O2	0.0325 (12)	0.0254 (12)	0.0273 (13)	0.0089 (10)	0.0197 (11)	0.0073 (10)
O3	0.0327 (13)	0.0219 (12)	0.0295 (13)	0.0083 (10)	0.0211 (11)	0.0095 (10)
O4	0.0253 (11)	0.0272 (12)	0.0160 (11)	0.0119 (9)	0.0086 (9)	0.0071 (10)
O5	0.0291 (12)	0.0354 (13)	0.0188 (12)	0.0186 (10)	0.0117 (10)	0.0119 (10)
O6	0.0292 (12)	0.0320 (13)	0.0190 (11)	0.0182 (10)	0.0119 (10)	0.0113 (10)
O7	0.0251 (12)	0.0394 (14)	0.0243 (12)	0.0182 (10)	0.0145 (10)	0.0168 (11)
O8	0.0280 (12)	0.0458 (15)	0.0253 (13)	0.0196 (11)	0.0161 (10)	0.0183 (11)
O9	0.0248 (12)	0.0392 (14)	0.0237 (12)	0.0175 (10)	0.0153 (10)	0.0157 (11)
O10	0.0624 (17)	0.0251 (14)	0.0473 (16)	0.0051 (12)	0.0399 (15)	0.0069 (12)
O11	0.0280 (12)	0.0377 (14)	0.0196 (12)	0.0158 (10)	0.0130 (10)	0.0123 (10)
O12	0.0315 (13)	0.0418 (14)	0.0240 (12)	0.0234 (11)	0.0155 (10)	0.0178 (11)
O13	0.0271 (13)	0.0688 (18)	0.0272 (13)	0.0275 (13)	0.0146 (11)	0.0238 (13)
N1	0.0276 (15)	0.0430 (18)	0.0291 (16)	0.0123 (13)	0.0137 (13)	0.0152 (14)
N2	0.0338 (16)	0.0351 (17)	0.0316 (16)	0.0160 (13)	0.0139 (13)	0.0170 (14)
C1	0.0338 (19)	0.0238 (18)	0.0276 (19)	0.0091 (15)	0.0082 (15)	0.0054 (15)
C2	0.0323 (19)	0.0286 (19)	0.0274 (19)	0.0091 (15)	0.0107 (16)	0.0085 (15)
C3	0.0325 (19)	0.0279 (19)	0.0270 (19)	0.0117 (15)	0.0102 (16)	0.0072 (15)
C4	0.0290 (19)	0.029 (2)	0.045 (2)	0.0075 (16)	0.0120 (17)	0.0087 (18)
C5	0.044 (2)	0.033 (2)	0.054 (3)	0.0065 (18)	0.024 (2)	0.014 (2)
C6	0.050 (2)	0.028 (2)	0.043 (2)	0.0132 (17)	0.0213 (19)	0.0194 (18)
C7	0.041 (2)	0.037 (2)	0.038 (2)	0.0188 (18)	0.0109 (18)	0.0096 (18)
C8	0.041 (2)	0.038 (2)	0.0250 (19)	0.0164 (17)	0.0063 (16)	0.0113 (17)

B1—O1	1.421 (4)	O13—H13A	0.8200
B1—O3	1.480 (4)	N1—C7	1.489 (5)
B1—O4	1.496 (4)	N1—H1A	0.8900
B1—O6	1.499 (4)	N1—H1B	0.8900
B2—O1	1.442 (4)	N1—H1C	0.8900
B2—O9	1.463 (4)	N2—C8	1.497 (4)
B2—O2	1.477 (4)	N2—H2A	0.8900
B2—O7	1.509 (4)	N2—H2B	0.8900
B3—O2	1.354 (4)	N2—H2C	0.8900
B3—O3	1.358 (4)	C1—C2	1.385 (5)
B3—O10	1.370 (4)	C1—C6	1.391 (5)
B4—O4	1.351 (4)	C1—C7	1.495 (5)
B4—O11	1.370 (4)	C2—C3	1.383 (5)
B4—O5	1.386 (4)	C2—H2D	0.9300
B5—O6	1.338 (4)	C3—C4	1.394 (5)
B5—O12	1.377 (4)	C3—C8	1.492 (5)
B5—O5	1.380 (4)	C4—C5	1.377 (6)
B6—O7	1.338 (4)	C4—H4A	0.9300
B6—O8	1.377 (4)	C5—C6	1.383 (5)
B6—O12i	1.388 (4)	C5—H5A	0.9300
B7—O9	1.332 (4)	C6—H6A	0.9300
B7—O13	1.368 (4)	C7—H7A	0.9700
B7—O8	1.388 (4)	C7—H7B	0.9700
O10—H10A	0.8200	C8—H8A	0.9700
O11—H11A	0.8200	C8—H8B	0.9700
O12—B6i	1.388 (4)
O1—B1—O3	112.6 (3)	C7—N1—H1B	109.5
O1—B1—O4	109.6 (3)	H1A—N1—H1B	109.5
O3—B1—O4	107.5 (2)	C7—N1—H1C	109.5
O1—B1—O6	111.1 (3)	H1A—N1—H1C	109.5
O3—B1—O6	107.2 (3)	H1B—N1—H1C	109.5
O4—B1—O6	108.6 (2)	C8—N2—H2A	109.5
O1—B2—O9	108.6 (3)	C8—N2—H2B	109.5
O1—B2—O2	112.9 (2)	H2A—N2—H2B	109.5
O9—B2—O2	109.0 (3)	C8—N2—H2C	109.5
O1—B2—O7	110.2 (3)	H2A—N2—H2C	109.5
O9—B2—O7	110.1 (2)	H2B—N2—H2C	109.5
O2—B2—O7	105.9 (3)	C2—C1—C6	118.9 (3)
O2—B3—O3	121.8 (3)	C2—C1—C7	118.6 (3)
O2—B3—O10	122.5 (3)	C6—C1—C7	122.2 (3)
O3—B3—O10	115.7 (3)	C3—C2—C1	121.5 (3)
O4—B4—O11	120.4 (3)	C3—C2—H2D	119.2
O4—B4—O5	121.5 (3)	C1—C2—H2D	119.2
O11—B4—O5	118.1 (3)	C2—C3—C4	118.6 (3)
O6—B5—O12	124.5 (3)	C2—C3—C8	120.2 (3)
O6—B5—O5	121.6 (3)	C4—C3—C8	120.9 (3)
O12—B5—O5	113.8 (3)	C5—C4—C3	120.5 (3)
O7—B6—O8	122.9 (3)	C5—C4—H4A	119.8
O7—B6—O12i	122.9 (3)	C3—C4—H4A	119.8
O8—B6—O12i	114.2 (3)	C4—C5—C6	120.3 (4)
O9—B7—O13	120.9 (3)	C4—C5—H5A	119.8
O9—B7—O8	122.5 (3)	C6—C5—H5A	119.8
O13—B7—O8	116.6 (3)	C5—C6—C1	120.1 (3)
B1—O1—B2	123.5 (3)	C5—C6—H6A	120.0
B3—O2—B2	122.1 (3)	C1—C6—H6A	120.0
B3—O3—B1	121.8 (2)	N1—C7—C1	109.5 (3)
B4—O4—B1	119.7 (3)	N1—C7—H7A	109.8
B5—O5—B4	118.9 (2)	C1—C7—H7A	109.8
B5—O6—B1	120.7 (2)	N1—C7—H7B	109.8
B6—O7—B2	122.4 (2)	C1—C7—H7B	109.8
B6—O8—B7	117.6 (3)	H7A—C7—H7B	108.2
B7—O9—B2	124.2 (3)	C3—C8—N2	108.3 (3)
B3—O10—H10A	109.5	C3—C8—H8A	110.0
B4—O11—H11A	109.5	N2—C8—H8A	110.0
B5—O12—B6i	132.5 (3)	C3—C8—H8B	110.0
B7—O13—H13A	109.5	N2—C8—H8B	110.0
C7—N1—H1A	109.5	H8A—C8—H8B	108.4

D—H···A	D—H	H···A	D···A	D—H···A
O10—H10A···O2ii	0.82	1.98	2.784 (2)	168
O11—H11A···O3iii	0.82	1.84	2.659 (2)	179
O13—H13A···O11iv	0.82	2.00	2.815 (2)	173
N1—H1A···O7	0.89	2.08	2.863 (2)	146
N1—H1B···O13v	0.89	1.98	2.850 (2)	166
N1—H1C···O6i	0.89	2.20	2.916 (2)	137
N1—H1C···O1i	0.89	2.54	3.394 (2)	161
N2—H2A···O4vi	0.89	1.97	2.822 (2)	159
N2—H2B···O1i	0.89	1.99	2.877 (2)	173
N2—H2B···O9i	0.89	2.55	3.052 (2)	116
N2—H2C···O12vii	0.89	2.19	3.067 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O10—H10A⋯O2i	0.82	1.98	2.784 (2)	168
O11—H11A⋯O3ii	0.82	1.84	2.659 (2)	179
O13—H13A⋯O11iii	0.82	2.00	2.815 (2)	173
N1—H1A⋯O7	0.89	2.08	2.863 (2)	146
N1—H1B⋯O13iv	0.89	1.98	2.850 (2)	166
N1—H1C⋯O6v	0.89	2.20	2.916 (2)	137
N1—H1C⋯O1v	0.89	2.54	3.394 (2)	161
N2—H2A⋯O4vi	0.89	1.97	2.822 (2)	159
N2—H2B⋯O1v	0.89	1.99	2.877 (2)	173
N2—H2B⋯O9v	0.89	2.55	3.052 (2)	116
N2—H2C⋯O12vii	0.89	2.19	3.067 (2)	168

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .