Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042146/bi2234sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042146/bi2234Isup2.hkl |
CCDC reference: 608071
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.129
- Data-to-parameter ratio = 12.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.24 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Barthel et al. (2000); Chen & Wu (1985); Downard et al. (2002); Green et al. (2000); Li & Liu (2006); Mori et al. (1995); Wu et al. (1993); Zhang et al. (2005).
A solution of boric acid (0.337 g) in 5 ml distilled water was added to a stirred solution of salicylic acid (1.394 g) in 10 ml of a mixed ethanol/water (1:1) solvent. The reaction mixture was stirred at 353 K for 20 min, then hexamethylenetetramine (0.725 g) was added slowly. After 4 h continued heating and stirring, the pH of the mixture had changed from 2 to 6, and the clear solution was then allowed to stand for 15 days at room temperature. The title compound was isolated as colorless transparent crystals. Elemental anlalysis calculated: C 56.62, N 13.21, H 5.00%; found C 56.76, N 13.00, H 4.86%.
All H atoms were positioned geometrically and refined as riding, with C—H = 0.93–0.97 Å or N—H = 0.91 Å, and with Uiso(H) = 1.2Ueq(C/N).
Inorganic borate compounds have been studied extensively since they can exhibit interesting physical properties, such as nonlinear optical behavior for CsLiB6O10 (Mori et al.,1995), CsB3O5 (Wu et al.,1993) and β-BaB2O4(Chen & Wu,1985). By contrast, studies of organic borates have been less extensive (Zhang et al., 2005; Downard et al., 2002; Green et al., 2000, Li & Liu, 2006). To date, alkali-metal bis(salicylato)borates have received the most attention (Zhang et al., 2005; Downard et al., 2002), since lithium organoborates have been considered as electrolytes for lithium batteries (Barthel et al., 2000). Herein, we report the synthesis and crystal structure of the salt of bis(salicylato)borate with the organic hexamethylenetetraminium cation.
The title compound is composed of [C6H13N4]+ cations and isolated [B(C7H4O3)2]- anions (Fig. 1). In the anion, the sp3-hybridized B atom is bonded to four O atoms in a tetrahedral geometry, with B—O distances in the range 1.444 (4)–1.480 (4) Å and O—B—O angles in the range 105.7 (2)–113.7 (2)°. Each salicylato ligand is approximately planar, and the ring plaes lie almost perpendicular to each other (dihedral angle 86.1 (1) °). In addition to electrostatic interactions between the cations and anions, N—H···O hydrogen bonds are formed between the N—H group of the cation and the two O atoms of one carboxylate group in the anion.
For related literature, see: Barthel et al. (2000); Chen & Wu (1985); Downard et al. (2002); Green et al. (2000); Li & Liu (2006); Mori et al. (1995); Wu et al. (1993); Zhang et al. (2005).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).
Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level for non-H atoms. |
C6H13N4+·C14H8BO6− | Z = 2 |
Mr = 424.22 | F(000) = 444 |
Triclinic, P1 | Dx = 1.452 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.697 (4) Å | Cell parameters from 1460 reflections |
b = 10.164 (5) Å | θ = 2.4–23.4° |
c = 12.212 (6) Å | µ = 0.11 mm−1 |
α = 71.111 (7)° | T = 298 K |
β = 72.765 (6)° | Plate, colourless |
γ = 79.160 (7)° | 0.41 × 0.29 × 0.12 mm |
V = 970.4 (8) Å3 |
Bruker SMART CCD area-detector diffractometer | 3382 independent reflections |
Radiation source: fine-focus sealed tube | 2132 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −10→10 |
Tmin = 0.957, Tmax = 0.987 | k = −12→8 |
5112 measured reflections | l = −14→14 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0485P)2 + 0.4284P] where P = (Fo2 + 2Fc2)/3 |
3382 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C6H13N4+·C14H8BO6− | γ = 79.160 (7)° |
Mr = 424.22 | V = 970.4 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.697 (4) Å | Mo Kα radiation |
b = 10.164 (5) Å | µ = 0.11 mm−1 |
c = 12.212 (6) Å | T = 298 K |
α = 71.111 (7)° | 0.41 × 0.29 × 0.12 mm |
β = 72.765 (6)° |
Bruker SMART CCD area-detector diffractometer | 3382 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | 2132 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.987 | Rint = 0.016 |
5112 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.25 e Å−3 |
3382 reflections | Δρmin = −0.16 e Å−3 |
280 parameters |
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 | ||
N1 | 0.6656 (3) | 0.7669 (2) | 0.5102 (2) | 0.0535 (6) | |
H1 | 0.5596 | 0.7527 | 0.5443 | 0.064* | |
N2 | 0.8490 (3) | 0.9067 (2) | 0.34266 (18) | 0.0470 (6) | |
N3 | 0.9283 (3) | 0.6597 (2) | 0.4279 (2) | 0.0527 (6) | |
N4 | 0.9022 (3) | 0.8249 (2) | 0.53993 (19) | 0.0492 (6) | |
O1 | 0.4850 (2) | 0.6951 (2) | 0.29242 (16) | 0.0559 (5) | |
O2 | 0.3403 (2) | 0.8933 (2) | 0.3087 (2) | 0.0759 (7) | |
O3 | 0.5212 (2) | 0.6141 (2) | 0.11880 (17) | 0.0584 (5) | |
O4 | 0.5638 (2) | 0.45922 (19) | 0.30073 (17) | 0.0566 (5) | |
O5 | 0.6526 (2) | 0.2370 (2) | 0.35252 (18) | 0.0632 (6) | |
O6 | 0.7469 (2) | 0.63698 (17) | 0.18453 (16) | 0.0481 (5) | |
B1 | 0.5799 (4) | 0.6034 (3) | 0.2206 (3) | 0.0477 (8) | |
C1 | 0.3984 (3) | 0.8123 (3) | 0.2488 (3) | 0.0515 (7) | |
C2 | 0.3747 (3) | 0.8344 (3) | 0.1294 (2) | 0.0475 (7) | |
C3 | 0.4371 (3) | 0.7340 (3) | 0.0697 (2) | 0.0466 (7) | |
C4 | 0.4102 (3) | 0.7520 (3) | −0.0412 (3) | 0.0609 (8) | |
H4 | 0.4525 | 0.6839 | −0.0810 | 0.073* | |
C5 | 0.3218 (4) | 0.8695 (4) | −0.0913 (3) | 0.0793 (10) | |
H5 | 0.3034 | 0.8810 | −0.1653 | 0.095* | |
C6 | 0.2594 (5) | 0.9713 (4) | −0.0342 (4) | 0.0895 (12) | |
H6 | 0.1995 | 1.0512 | −0.0695 | 0.107* | |
C7 | 0.2856 (4) | 0.9548 (3) | 0.0761 (3) | 0.0740 (9) | |
H7 | 0.2439 | 1.0239 | 0.1148 | 0.089* | |
C8 | 0.6813 (3) | 0.3568 (3) | 0.2937 (2) | 0.0454 (6) | |
C9 | 0.8423 (3) | 0.3944 (3) | 0.2199 (2) | 0.0387 (6) | |
C10 | 0.8691 (3) | 0.5344 (3) | 0.1716 (2) | 0.0386 (6) | |
C11 | 1.0252 (3) | 0.5703 (3) | 0.1124 (2) | 0.0451 (6) | |
H11 | 1.0449 | 0.6638 | 0.0825 | 0.054* | |
C12 | 1.1496 (3) | 0.4677 (3) | 0.0983 (2) | 0.0494 (7) | |
H12 | 1.2537 | 0.4924 | 0.0586 | 0.059* | |
C13 | 1.1237 (3) | 0.3283 (3) | 0.1418 (2) | 0.0512 (7) | |
H13 | 1.2090 | 0.2597 | 0.1297 | 0.061* | |
C14 | 0.9706 (3) | 0.2917 (3) | 0.2033 (2) | 0.0466 (6) | |
H14 | 0.9525 | 0.1979 | 0.2340 | 0.056* | |
C15 | 0.6829 (3) | 0.8848 (3) | 0.3955 (2) | 0.0543 (7) | |
H15A | 0.6388 | 0.8623 | 0.3402 | 0.065* | |
H15B | 0.6224 | 0.9697 | 0.4120 | 0.065* | |
C16 | 0.7608 (3) | 0.6371 (3) | 0.4823 (3) | 0.0552 (7) | |
H16A | 0.7519 | 0.5605 | 0.5554 | 0.066* | |
H16B | 0.7169 | 0.6119 | 0.4284 | 0.066* | |
C17 | 0.7364 (4) | 0.8026 (3) | 0.5945 (2) | 0.0602 (8) | |
H17A | 0.6768 | 0.8864 | 0.6139 | 0.072* | |
H17B | 0.7274 | 0.7269 | 0.6682 | 0.072* | |
C18 | 0.9388 (3) | 0.7771 (3) | 0.3193 (2) | 0.0581 (8) | |
H18A | 0.8966 | 0.7536 | 0.2636 | 0.070* | |
H18B | 1.0516 | 0.7923 | 0.2819 | 0.070* | |
C19 | 0.9915 (4) | 0.6990 (3) | 0.5116 (3) | 0.0616 (8) | |
H19A | 0.9846 | 0.6228 | 0.5848 | 0.074* | |
H19B | 1.1047 | 0.7142 | 0.4762 | 0.074* | |
C20 | 0.9137 (3) | 0.9386 (3) | 0.4284 (2) | 0.0529 (7) | |
H20A | 1.0262 | 0.9558 | 0.3923 | 0.063* | |
H20B | 0.8544 | 1.0232 | 0.4463 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0462 (13) | 0.0528 (14) | 0.0587 (14) | −0.0155 (11) | −0.0064 (11) | −0.0128 (12) |
N2 | 0.0548 (14) | 0.0414 (13) | 0.0469 (13) | −0.0137 (11) | −0.0184 (10) | −0.0054 (10) |
N3 | 0.0558 (14) | 0.0398 (13) | 0.0622 (15) | −0.0049 (11) | −0.0133 (11) | −0.0152 (12) |
N4 | 0.0609 (15) | 0.0421 (13) | 0.0519 (13) | −0.0069 (11) | −0.0258 (11) | −0.0118 (11) |
O1 | 0.0525 (11) | 0.0609 (13) | 0.0593 (12) | 0.0089 (10) | −0.0192 (9) | −0.0274 (10) |
O2 | 0.0596 (13) | 0.0812 (16) | 0.0983 (16) | 0.0059 (11) | −0.0110 (11) | −0.0560 (14) |
O3 | 0.0576 (12) | 0.0595 (13) | 0.0687 (13) | 0.0102 (10) | −0.0274 (10) | −0.0314 (11) |
O4 | 0.0387 (10) | 0.0484 (12) | 0.0714 (13) | −0.0031 (9) | −0.0071 (9) | −0.0089 (10) |
O5 | 0.0564 (12) | 0.0436 (12) | 0.0716 (13) | −0.0113 (9) | −0.0012 (10) | −0.0028 (10) |
O6 | 0.0428 (10) | 0.0386 (10) | 0.0615 (11) | −0.0017 (8) | −0.0136 (8) | −0.0133 (9) |
B1 | 0.0408 (17) | 0.0463 (19) | 0.0586 (19) | 0.0062 (14) | −0.0179 (15) | −0.0194 (16) |
C1 | 0.0338 (15) | 0.0531 (18) | 0.0683 (19) | −0.0066 (13) | −0.0033 (13) | −0.0260 (16) |
C2 | 0.0363 (14) | 0.0405 (16) | 0.0623 (17) | −0.0061 (12) | −0.0107 (12) | −0.0106 (14) |
C3 | 0.0369 (14) | 0.0477 (17) | 0.0543 (17) | −0.0115 (12) | −0.0118 (12) | −0.0091 (14) |
C4 | 0.0569 (18) | 0.067 (2) | 0.0607 (19) | −0.0179 (16) | −0.0176 (15) | −0.0121 (16) |
C5 | 0.085 (3) | 0.076 (3) | 0.072 (2) | −0.023 (2) | −0.0296 (19) | 0.002 (2) |
C6 | 0.089 (3) | 0.065 (3) | 0.096 (3) | −0.003 (2) | −0.044 (2) | 0.018 (2) |
C7 | 0.072 (2) | 0.0458 (19) | 0.096 (3) | −0.0008 (16) | −0.0225 (19) | −0.0111 (18) |
C8 | 0.0453 (15) | 0.0425 (16) | 0.0464 (15) | −0.0067 (13) | −0.0117 (12) | −0.0085 (13) |
C9 | 0.0399 (14) | 0.0406 (15) | 0.0339 (13) | −0.0042 (11) | −0.0094 (11) | −0.0082 (11) |
C10 | 0.0403 (14) | 0.0413 (15) | 0.0361 (13) | −0.0035 (11) | −0.0128 (11) | −0.0110 (12) |
C11 | 0.0509 (16) | 0.0434 (15) | 0.0425 (14) | −0.0133 (13) | −0.0071 (12) | −0.0138 (12) |
C12 | 0.0410 (15) | 0.0607 (19) | 0.0465 (15) | −0.0104 (13) | −0.0026 (12) | −0.0200 (14) |
C13 | 0.0451 (16) | 0.0522 (18) | 0.0523 (16) | 0.0035 (13) | −0.0082 (13) | −0.0182 (14) |
C14 | 0.0525 (17) | 0.0382 (15) | 0.0449 (15) | −0.0039 (13) | −0.0123 (13) | −0.0066 (12) |
C15 | 0.0504 (17) | 0.0540 (18) | 0.0580 (17) | −0.0048 (13) | −0.0236 (14) | −0.0065 (15) |
C16 | 0.0667 (19) | 0.0416 (16) | 0.0596 (17) | −0.0136 (14) | −0.0147 (14) | −0.0141 (14) |
C17 | 0.074 (2) | 0.062 (2) | 0.0469 (16) | −0.0067 (16) | −0.0154 (15) | −0.0184 (15) |
C18 | 0.0597 (18) | 0.0584 (19) | 0.0549 (17) | −0.0112 (15) | −0.0038 (14) | −0.0211 (15) |
C19 | 0.0613 (19) | 0.0535 (19) | 0.071 (2) | 0.0036 (15) | −0.0311 (16) | −0.0114 (16) |
C20 | 0.0615 (18) | 0.0426 (16) | 0.0614 (17) | −0.0148 (13) | −0.0249 (14) | −0.0102 (14) |
N1—C16 | 1.502 (3) | C5—C6 | 1.372 (5) |
N1—C17 | 1.507 (3) | C5—H5 | 0.930 |
N1—C15 | 1.510 (3) | C6—C7 | 1.384 (5) |
N1—H1 | 0.910 | C6—H6 | 0.930 |
N2—C15 | 1.424 (3) | C7—H7 | 0.930 |
N2—C18 | 1.467 (3) | C8—C9 | 1.466 (3) |
N2—C20 | 1.468 (3) | C9—C10 | 1.388 (3) |
N3—C16 | 1.439 (3) | C9—C14 | 1.393 (3) |
N3—C18 | 1.461 (3) | C10—C11 | 1.391 (3) |
N3—C19 | 1.479 (3) | C11—C12 | 1.367 (3) |
N4—C17 | 1.425 (3) | C11—H11 | 0.930 |
N4—C19 | 1.454 (3) | C12—C13 | 1.379 (4) |
N4—C20 | 1.464 (3) | C12—H12 | 0.930 |
O1—C1 | 1.326 (3) | C13—C14 | 1.374 (4) |
O1—B1 | 1.460 (3) | C13—H13 | 0.930 |
O2—C1 | 1.217 (3) | C14—H14 | 0.930 |
O3—C3 | 1.353 (3) | C15—H15A | 0.970 |
O3—B1 | 1.444 (4) | C15—H15B | 0.970 |
O4—C8 | 1.320 (3) | C16—H16A | 0.970 |
O4—B1 | 1.480 (4) | C16—H16B | 0.970 |
O5—C8 | 1.226 (3) | C17—H17A | 0.970 |
O6—C10 | 1.354 (3) | C17—H17B | 0.970 |
O6—B1 | 1.460 (3) | C18—H18A | 0.970 |
C1—C2 | 1.473 (4) | C18—H18B | 0.970 |
C2—C3 | 1.380 (4) | C19—H19A | 0.970 |
C2—C7 | 1.395 (4) | C19—H19B | 0.970 |
C3—C4 | 1.390 (4) | C20—H20A | 0.970 |
C4—C5 | 1.361 (4) | C20—H20B | 0.970 |
C4—H4 | 0.930 | ||
C16—N1—C17 | 108.2 (2) | O6—C10—C9 | 121.3 (2) |
C16—N1—C15 | 108.6 (2) | O6—C10—C11 | 119.2 (2) |
C17—N1—C15 | 109.0 (2) | C9—C10—C11 | 119.5 (2) |
C16—N1—H1 | 110.4 | C12—C11—C10 | 119.7 (2) |
C17—N1—H1 | 110.4 | C12—C11—H11 | 120.1 |
C15—N1—H1 | 110.4 | C10—C11—H11 | 120.1 |
C15—N2—C18 | 108.9 (2) | C11—C12—C13 | 121.3 (2) |
C15—N2—C20 | 108.7 (2) | C11—C12—H12 | 119.3 |
C18—N2—C20 | 107.8 (2) | C13—C12—H12 | 119.3 |
C16—N3—C18 | 108.7 (2) | C14—C13—C12 | 119.3 (3) |
C16—N3—C19 | 108.4 (2) | C14—C13—H13 | 120.4 |
C18—N3—C19 | 107.9 (2) | C12—C13—H13 | 120.4 |
C17—N4—C19 | 109.7 (2) | C13—C14—C9 | 120.4 (2) |
C17—N4—C20 | 109.0 (2) | C13—C14—H14 | 119.8 |
C19—N4—C20 | 108.4 (2) | C9—C14—H14 | 119.8 |
C1—O1—B1 | 123.2 (2) | N2—C15—N1 | 110.1 (2) |
C3—O3—B1 | 119.7 (2) | N2—C15—H15A | 109.6 |
C8—O4—B1 | 122.7 (2) | N1—C15—H15A | 109.6 |
C10—O6—B1 | 119.2 (2) | N2—C15—H15B | 109.6 |
O3—B1—O6 | 111.8 (2) | N1—C15—H15B | 109.6 |
O3—B1—O1 | 113.7 (2) | H15A—C15—H15B | 108.1 |
O6—B1—O1 | 106.8 (2) | N3—C16—N1 | 110.4 (2) |
O3—B1—O4 | 107.4 (2) | N3—C16—H16A | 109.6 |
O6—B1—O4 | 111.4 (2) | N1—C16—H16A | 109.6 |
O1—B1—O4 | 105.7 (2) | N3—C16—H16B | 109.6 |
O2—C1—O1 | 119.7 (3) | N1—C16—H16B | 109.6 |
O2—C1—C2 | 123.6 (3) | H16A—C16—H16B | 108.1 |
O1—C1—C2 | 116.7 (2) | N4—C17—N1 | 109.7 (2) |
C3—C2—C7 | 119.0 (3) | N4—C17—H17A | 109.7 |
C3—C2—C1 | 120.2 (2) | N1—C17—H17A | 109.7 |
C7—C2—C1 | 120.8 (3) | N4—C17—H17B | 109.7 |
O3—C3—C2 | 121.1 (2) | N1—C17—H17B | 109.7 |
O3—C3—C4 | 118.3 (3) | H17A—C17—H17B | 108.2 |
C2—C3—C4 | 120.5 (3) | N3—C18—N2 | 112.8 (2) |
C5—C4—C3 | 119.8 (3) | N3—C18—H18A | 109.0 |
C5—C4—H4 | 120.1 | N2—C18—H18A | 109.0 |
C3—C4—H4 | 120.1 | N3—C18—H18B | 109.0 |
C4—C5—C6 | 120.9 (3) | N2—C18—H18B | 109.0 |
C4—C5—H5 | 119.6 | H18A—C18—H18B | 107.8 |
C6—C5—H5 | 119.6 | N4—C19—N3 | 111.9 (2) |
C5—C6—C7 | 119.9 (3) | N4—C19—H19A | 109.2 |
C5—C6—H6 | 120.0 | N3—C19—H19A | 109.2 |
C7—C6—H6 | 120.0 | N4—C19—H19B | 109.2 |
C6—C7—C2 | 120.0 (3) | N3—C19—H19B | 109.2 |
C6—C7—H7 | 120.0 | H19A—C19—H19B | 107.9 |
C2—C7—H7 | 120.0 | N4—C20—N2 | 112.3 (2) |
O5—C8—O4 | 118.9 (2) | N4—C20—H20A | 109.1 |
O5—C8—C9 | 123.5 (2) | N2—C20—H20A | 109.1 |
O4—C8—C9 | 117.6 (2) | N4—C20—H20B | 109.1 |
C10—C9—C14 | 119.6 (2) | N2—C20—H20B | 109.1 |
C10—C9—C8 | 119.3 (2) | H20A—C20—H20B | 107.9 |
C14—C9—C8 | 120.9 (2) | ||
C3—O3—B1—O6 | −94.9 (3) | B1—O6—C10—C9 | −16.5 (3) |
C3—O3—B1—O1 | 26.1 (3) | B1—O6—C10—C11 | 165.7 (2) |
C3—O3—B1—O4 | 142.7 (2) | C14—C9—C10—O6 | 179.1 (2) |
C10—O6—B1—O3 | −87.8 (3) | C8—C9—C10—O6 | −4.6 (3) |
C10—O6—B1—O1 | 147.3 (2) | C14—C9—C10—C11 | −3.2 (3) |
C10—O6—B1—O4 | 32.4 (3) | C8—C9—C10—C11 | 173.2 (2) |
C1—O1—B1—O3 | −25.2 (4) | O6—C10—C11—C12 | −179.7 (2) |
C1—O1—B1—O6 | 98.5 (3) | C9—C10—C11—C12 | 2.5 (4) |
C1—O1—B1—O4 | −142.8 (2) | C10—C11—C12—C13 | 0.0 (4) |
C8—O4—B1—O3 | 91.8 (3) | C11—C12—C13—C14 | −1.7 (4) |
C8—O4—B1—O6 | −30.9 (3) | C12—C13—C14—C9 | 1.0 (4) |
C8—O4—B1—O1 | −146.5 (2) | C10—C9—C14—C13 | 1.4 (4) |
B1—O1—C1—O2 | −170.0 (2) | C8—C9—C14—C13 | −174.8 (2) |
B1—O1—C1—C2 | 11.6 (4) | C18—N2—C15—N1 | 58.8 (3) |
O2—C1—C2—C3 | −176.4 (2) | C20—N2—C15—N1 | −58.5 (3) |
O1—C1—C2—C3 | 1.9 (3) | C16—N1—C15—N2 | −59.0 (3) |
O2—C1—C2—C7 | 1.9 (4) | C17—N1—C15—N2 | 58.6 (3) |
O1—C1—C2—C7 | −179.8 (2) | C18—N3—C16—N1 | −58.2 (3) |
B1—O3—C3—C2 | −14.7 (4) | C19—N3—C16—N1 | 58.8 (3) |
B1—O3—C3—C4 | 167.4 (2) | C17—N1—C16—N3 | −59.5 (3) |
C7—C2—C3—O3 | −178.5 (2) | C15—N1—C16—N3 | 58.6 (3) |
C1—C2—C3—O3 | −0.2 (4) | C19—N4—C17—N1 | −59.7 (3) |
C7—C2—C3—C4 | −0.6 (4) | C20—N4—C17—N1 | 58.9 (3) |
C1—C2—C3—C4 | 177.7 (2) | C16—N1—C17—N4 | 59.3 (3) |
O3—C3—C4—C5 | 178.0 (3) | C15—N1—C17—N4 | −58.5 (3) |
C2—C3—C4—C5 | 0.0 (4) | C16—N3—C18—N2 | 59.2 (3) |
C3—C4—C5—C6 | 0.4 (5) | C19—N3—C18—N2 | −58.1 (3) |
C4—C5—C6—C7 | −0.2 (5) | C15—N2—C18—N3 | −59.9 (3) |
C5—C6—C7—C2 | −0.3 (5) | C20—N2—C18—N3 | 57.9 (3) |
C3—C2—C7—C6 | 0.8 (4) | C17—N4—C19—N3 | 60.2 (3) |
C1—C2—C7—C6 | −177.5 (3) | C20—N4—C19—N3 | −58.8 (3) |
B1—O4—C8—O5 | −170.9 (2) | C16—N3—C19—N4 | −59.2 (3) |
B1—O4—C8—C9 | 12.1 (4) | C18—N3—C19—N4 | 58.3 (3) |
O5—C8—C9—C10 | −169.9 (2) | C17—N4—C20—N2 | −60.5 (3) |
O4—C8—C9—C10 | 6.9 (3) | C19—N4—C20—N2 | 58.8 (3) |
O5—C8—C9—C14 | 6.4 (4) | C15—N2—C20—N4 | 60.1 (3) |
O4—C8—C9—C14 | −176.8 (2) | C18—N2—C20—N4 | −57.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5i | 0.91 | 1.91 | 2.778 (3) | 160 |
N1—H1···O4i | 0.91 | 2.53 | 3.186 (3) | 129 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C6H13N4+·C14H8BO6− |
Mr | 424.22 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 8.697 (4), 10.164 (5), 12.212 (6) |
α, β, γ (°) | 71.111 (7), 72.765 (6), 79.160 (7) |
V (Å3) | 970.4 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.41 × 0.29 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1999) |
Tmin, Tmax | 0.957, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5112, 3382, 2132 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.129, 1.02 |
No. of reflections | 3382 |
No. of parameters | 280 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.16 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5i | 0.91 | 1.91 | 2.778 (3) | 160 |
N1—H1···O4i | 0.91 | 2.53 | 3.186 (3) | 129 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Inorganic borate compounds have been studied extensively since they can exhibit interesting physical properties, such as nonlinear optical behavior for CsLiB6O10 (Mori et al.,1995), CsB3O5 (Wu et al.,1993) and β-BaB2O4(Chen & Wu,1985). By contrast, studies of organic borates have been less extensive (Zhang et al., 2005; Downard et al., 2002; Green et al., 2000, Li & Liu, 2006). To date, alkali-metal bis(salicylato)borates have received the most attention (Zhang et al., 2005; Downard et al., 2002), since lithium organoborates have been considered as electrolytes for lithium batteries (Barthel et al., 2000). Herein, we report the synthesis and crystal structure of the salt of bis(salicylato)borate with the organic hexamethylenetetraminium cation.
The title compound is composed of [C6H13N4]+ cations and isolated [B(C7H4O3)2]- anions (Fig. 1). In the anion, the sp3-hybridized B atom is bonded to four O atoms in a tetrahedral geometry, with B—O distances in the range 1.444 (4)–1.480 (4) Å and O—B—O angles in the range 105.7 (2)–113.7 (2)°. Each salicylato ligand is approximately planar, and the ring plaes lie almost perpendicular to each other (dihedral angle 86.1 (1) °). In addition to electrostatic interactions between the cations and anions, N—H···O hydrogen bonds are formed between the N—H group of the cation and the two O atoms of one carboxylate group in the anion.