Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001961/bi2144sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001961/bi2144Isup2.hkl |
CCDC reference: 624870
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.054
- wR factor = 0.145
- Data-to-parameter ratio = 14.0
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 . ? PLAT223_ALERT_4_C Large Solvent/Anion H Ueq(max)/Ueq(min) ... 3.24 Ratio PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.54 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C2 - C3 ... 1.35 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C3 - C4 ... 1.42 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C4H12N+·B5H4O10− | F(000) = 608 |
Mr = 292.23 | Dx = 1.437 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2750 reflections |
a = 9.4025 (3) Å | θ = 3.2–26.5° |
b = 13.6395 (5) Å | µ = 0.13 mm−1 |
c = 10.5395 (4) Å | T = 293 K |
β = 91.956 (2)° | Prism, colourless |
V = 1350.85 (8) Å3 | 0.25 × 0.22 × 0.15 mm |
Z = 4 |
Siemens SMART CCD diffractometer | 2750 independent reflections |
Radiation source: fine-focus sealed tube | 2274 reflections with I > 2˘I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 26.5°, θmin = 3.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→11 |
Tmin = 0.969, Tmax = 0.981 | k = −17→17 |
9341 measured reflections | l = −13→12 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0651P)2 + 0.8653P] where P = (Fo2 + 2Fc2)/3 |
2750 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.56 e Å−3 |
11 restraints | Δρmin = −0.50 e Å−3 |
Experimental. The IR spectrum of (I) exhibits the characteristic bands of BO3 and BO4 groups, corresponding to the two strong bands at about 1310 cm-1 and 1016 cm-1, respectively [Yu, Z. T., Shi, Z., Jiang, Y. S., Yuan, H. M., Chen, J. S. (2002). Chem. Mater. 14, 1314–1318]. Peaks at 3362, 3185, 2962, 2883, and 1425 cm-1 are consistent with the existence of the organic amine. Thermogravimetric analysis (TG) was performed in dry O2 atmosphere from 303 to 1273 K, with a heating rate of 10 K min-1. The TG curve of (I) showed a continuous weight loss from 503 to 913 K, corresponding to the removal of the organic amine and the dehydration of hydroxyls (Found: 39.90%, Calcd: 41.80%). |
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 | 0.0323 (2) | 0.58159 (17) | 0.6157 (2) | 0.0295 (5) | |
B2 | 0.1088 (2) | 0.69954 (18) | 0.4665 (2) | 0.0325 (5) | |
B3 | 0.2839 (2) | 0.63088 (17) | 0.6218 (2) | 0.0281 (5) | |
B4 | 0.4477 (2) | 0.72477 (19) | 0.7629 (2) | 0.0347 (5) | |
B5 | 0.5445 (2) | 0.60862 (18) | 0.6211 (2) | 0.0320 (5) | |
O1 | −0.06989 (16) | 0.52391 (13) | 0.66212 (17) | 0.0446 (4) | |
H1 | −0.153 (3) | 0.539 (2) | 0.638 (3) | 0.067* | |
O2 | −0.00107 (14) | 0.65537 (11) | 0.52945 (14) | 0.0348 (4) | |
O3 | 0.07000 (17) | 0.75306 (15) | 0.36319 (17) | 0.0516 (5) | |
H3 | 0.144 (3) | 0.773 (3) | 0.331 (3) | 0.077* | |
O4 | 0.16983 (14) | 0.56360 (10) | 0.65255 (13) | 0.0311 (3) | |
O5 | 0.24580 (14) | 0.68808 (11) | 0.50745 (13) | 0.0340 (4) | |
O6 | 0.41180 (13) | 0.57348 (11) | 0.59378 (13) | 0.0312 (3) | |
O7 | 0.31394 (14) | 0.69643 (11) | 0.73020 (13) | 0.0341 (4) | |
O8 | 0.47914 (18) | 0.79119 (15) | 0.85489 (18) | 0.0538 (5) | |
H8 | 0.403 (3) | 0.806 (3) | 0.889 (3) | 0.081* | |
O9 | 0.56443 (15) | 0.68716 (12) | 0.70213 (16) | 0.0420 (4) | |
O10 | 0.66077 (15) | 0.56716 (13) | 0.57112 (16) | 0.0421 (4) | |
H10 | 0.640 (3) | 0.5212 (19) | 0.521 (3) | 0.063* | |
N1 | 0.7878 (2) | 0.85780 (18) | 0.7948 (2) | 0.0585 (6) | |
H1C | 0.8493 | 0.8237 | 0.8433 | 0.088* | |
H1D | 0.7015 | 0.8316 | 0.7996 | 0.088* | |
H1E | 0.7858 | 0.9196 | 0.8216 | 0.088* | |
C1 | 0.8319 (4) | 0.8553 (3) | 0.6627 (3) | 0.0859 (11) | |
H1A | 0.8344 | 0.7879 | 0.6334 | 0.103* | |
H1B | 0.9269 | 0.8824 | 0.6575 | 0.103* | |
C2 | 0.7314 (6) | 0.9127 (6) | 0.5807 (5) | 0.154 (3) | |
H2A | 0.6632 | 0.8667 | 0.5435 | 0.185* | |
H2B | 0.6789 | 0.9554 | 0.6360 | 0.185* | |
C3 | 0.7784 (8) | 0.9687 (7) | 0.4856 (10) | 0.237 (6) | |
H3A | 0.8207 | 0.9240 | 0.4259 | 0.285* | |
H3B | 0.8559 | 1.0077 | 0.5218 | 0.285* | |
C4 | 0.6922 (7) | 1.0340 (4) | 0.4118 (5) | 0.133 (2) | |
H4A | 0.7468 | 1.0610 | 0.3450 | 0.200* | |
H4B | 0.6595 | 1.0860 | 0.4649 | 0.200* | |
H4C | 0.6118 | 0.9991 | 0.3758 | 0.200* |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.0179 (9) | 0.0367 (12) | 0.0338 (11) | −0.0001 (8) | 0.0001 (8) | −0.0031 (9) |
B2 | 0.0213 (10) | 0.0410 (12) | 0.0352 (12) | 0.0022 (9) | −0.0004 (9) | 0.0014 (9) |
B3 | 0.0160 (9) | 0.0387 (12) | 0.0296 (11) | −0.0002 (8) | −0.0004 (8) | −0.0028 (9) |
B4 | 0.0233 (10) | 0.0454 (13) | 0.0352 (12) | −0.0024 (9) | 0.0000 (9) | −0.0067 (10) |
B5 | 0.0195 (10) | 0.0430 (13) | 0.0334 (11) | −0.0002 (9) | −0.0030 (8) | −0.0049 (9) |
O1 | 0.0204 (7) | 0.0534 (10) | 0.0597 (10) | −0.0049 (7) | −0.0015 (7) | 0.0143 (8) |
O2 | 0.0184 (6) | 0.0458 (8) | 0.0402 (8) | 0.0032 (6) | −0.0002 (5) | 0.0041 (6) |
O3 | 0.0282 (8) | 0.0731 (12) | 0.0530 (10) | 0.0010 (8) | −0.0042 (7) | 0.0252 (9) |
O4 | 0.0172 (7) | 0.0397 (8) | 0.0363 (7) | −0.0017 (5) | −0.0015 (5) | 0.0034 (6) |
O5 | 0.0201 (7) | 0.0470 (8) | 0.0347 (8) | −0.0030 (6) | −0.0016 (5) | 0.0064 (6) |
O6 | 0.0162 (7) | 0.0402 (8) | 0.0370 (7) | 0.0011 (5) | −0.0006 (5) | −0.0081 (6) |
O7 | 0.0197 (7) | 0.0474 (8) | 0.0352 (8) | 0.0003 (6) | 0.0002 (5) | −0.0118 (6) |
O8 | 0.0284 (8) | 0.0741 (12) | 0.0589 (11) | −0.0075 (8) | 0.0014 (7) | −0.0352 (9) |
O9 | 0.0191 (7) | 0.0567 (10) | 0.0502 (9) | −0.0053 (6) | 0.0007 (6) | −0.0199 (7) |
O10 | 0.0171 (7) | 0.0563 (10) | 0.0527 (10) | 0.0017 (6) | −0.0014 (6) | −0.0188 (7) |
N1 | 0.0386 (11) | 0.0655 (14) | 0.0702 (15) | −0.0071 (10) | −0.0152 (10) | 0.0030 (12) |
C1 | 0.068 (2) | 0.104 (3) | 0.086 (2) | 0.000 (2) | 0.0077 (18) | −0.034 (2) |
C2 | 0.108 (4) | 0.272 (9) | 0.079 (3) | −0.041 (5) | −0.030 (3) | 0.040 (4) |
C3 | 0.140 (7) | 0.219 (9) | 0.352 (15) | 0.022 (6) | −0.010 (8) | 0.174 (10) |
C4 | 0.170 (6) | 0.126 (4) | 0.106 (4) | 0.019 (4) | 0.028 (4) | 0.005 (3) |
B1—O1 | 1.347 (3) | O8—H8 | 0.84 (2) |
B1—O2 | 1.385 (3) | O10—H10 | 0.84 (2) |
B1—O4 | 1.360 (2) | N1—C1 | 1.466 (4) |
B2—O2 | 1.384 (3) | N1—H1C | 0.890 |
B2—O3 | 1.351 (3) | N1—H1D | 0.890 |
B2—O5 | 1.354 (3) | N1—H1E | 0.890 |
B3—O4 | 1.456 (3) | C1—C2 | 1.483 (6) |
B3—O5 | 1.470 (3) | C1—H1A | 0.970 |
B3—O6 | 1.473 (2) | C1—H1B | 0.970 |
B3—O7 | 1.470 (3) | C2—C3 | 1.347 (7) |
B4—O7 | 1.350 (3) | C2—H2A | 0.970 |
B4—O8 | 1.352 (3) | C2—H2B | 0.970 |
B4—O9 | 1.387 (3) | C3—C4 | 1.419 (6) |
B5—O6 | 1.358 (2) | C3—H3A | 0.970 |
B5—O9 | 1.379 (3) | C3—H3B | 0.970 |
B5—O10 | 1.353 (3) | C4—H4A | 0.960 |
O1—H1 | 0.84 (2) | C4—H4B | 0.960 |
O3—H3 | 0.84 (2) | C4—H4C | 0.960 |
O1—B1—O4 | 118.28 (19) | C1—N1—H1D | 109.5 |
O1—B1—O2 | 120.98 (18) | H1C—N1—H1D | 109.5 |
O4—B1—O2 | 120.71 (18) | C1—N1—H1E | 109.5 |
O3—B2—O5 | 123.2 (2) | H1C—N1—H1E | 109.5 |
O3—B2—O2 | 115.86 (18) | H1D—N1—H1E | 109.5 |
O5—B2—O2 | 120.97 (19) | N1—C1—C2 | 110.2 (4) |
O4—B3—O5 | 110.87 (15) | N1—C1—H1A | 109.6 |
O4—B3—O7 | 109.48 (16) | C2—C1—H1A | 109.6 |
O5—B3—O7 | 110.45 (17) | N1—C1—H1B | 109.6 |
O4—B3—O6 | 108.79 (17) | C2—C1—H1B | 109.6 |
O5—B3—O6 | 107.19 (15) | H1A—C1—H1B | 108.1 |
O7—B3—O6 | 110.02 (15) | C3—C2—C1 | 120.9 (5) |
O7—B4—O8 | 123.6 (2) | C3—C2—H2A | 107.1 |
O7—B4—O9 | 121.40 (19) | C1—C2—H2A | 107.1 |
O8—B4—O9 | 114.97 (19) | C3—C2—H2B | 107.1 |
O10—B5—O6 | 121.24 (19) | C1—C2—H2B | 107.1 |
O10—B5—O9 | 118.12 (18) | H2A—C2—H2B | 106.8 |
O6—B5—O9 | 120.63 (18) | C2—C3—C4 | 124.6 (7) |
B1—O1—H1 | 115 (2) | C2—C3—H3A | 106.2 |
B2—O2—B1 | 118.34 (16) | C4—C3—H3A | 106.2 |
B2—O3—H3 | 108 (3) | C2—C3—H3B | 106.2 |
B1—O4—B3 | 121.53 (16) | C4—C3—H3B | 106.2 |
B2—O5—B3 | 121.69 (16) | H3A—C3—H3B | 106.4 |
B5—O6—B3 | 121.35 (16) | C3—C4—H4A | 109.5 |
B4—O7—B3 | 121.68 (16) | C3—C4—H4B | 109.5 |
B4—O8—H8 | 107 (3) | H4A—C4—H4B | 109.5 |
B5—O9—B4 | 118.72 (17) | C3—C4—H4C | 109.5 |
B5—O10—H10 | 112 (2) | H4A—C4—H4C | 109.5 |
C1—N1—H1C | 109.5 | H4B—C4—H4C | 109.5 |
O3—B2—O2—B1 | 164.6 (2) | O9—B5—O6—B3 | 15.6 (3) |
O5—B2—O2—B1 | −15.0 (3) | O4—B3—O6—B5 | −148.02 (18) |
O1—B1—O2—B2 | −167.7 (2) | O5—B3—O6—B5 | 92.0 (2) |
O4—B1—O2—B2 | 10.3 (3) | O7—B3—O6—B5 | −28.1 (3) |
O1—B1—O4—B3 | −170.85 (18) | O8—B4—O7—B3 | 174.3 (2) |
O2—B1—O4—B3 | 11.1 (3) | O9—B4—O7—B3 | −5.3 (3) |
O5—B3—O4—B1 | −25.4 (2) | O4—B3—O7—B4 | 142.40 (19) |
O7—B3—O4—B1 | 96.7 (2) | O5—B3—O7—B4 | −95.2 (2) |
O6—B3—O4—B1 | −143.05 (17) | O6—B3—O7—B4 | 22.9 (3) |
O3—B2—O5—B3 | 178.8 (2) | O10—B5—O9—B4 | −174.3 (2) |
O2—B2—O5—B3 | −1.7 (3) | O6—B5—O9—B4 | 4.9 (3) |
O4—B3—O5—B2 | 20.7 (3) | O7—B4—O9—B5 | −10.2 (3) |
O7—B3—O5—B2 | −100.8 (2) | O8—B4—O9—B5 | 170.3 (2) |
O6—B3—O5—B2 | 139.35 (19) | N1—C1—C2—C3 | 141.1 (9) |
O10—B5—O6—B3 | −165.20 (19) | C1—C2—C3—C4 | −172.7 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1D···O8 | 0.89 | 2.26 | 3.127 (3) | 165 |
N1—H1D···O9 | 0.89 | 2.55 | 3.262 (3) | 137 |
N1—H1C···O2i | 0.89 | 2.39 | 3.123 (3) | 140 |
N1—H1C···O3i | 0.89 | 2.33 | 3.117 (3) | 148 |
N1—H1E···O4ii | 0.89 | 2.02 | 2.886 (3) | 163 |
O1—H1···O10iii | 0.84 (2) | 1.90 (2) | 2.741 (2) | 175 (3) |
O3—H3···O7iv | 0.84 (2) | 1.99 (2) | 2.814 (2) | 170 (4) |
O8—H8···O5v | 0.84 (2) | 1.97 (3) | 2.778 (2) | 162 (4) |
O10—H10···O6vi | 0.84 (2) | 1.83 (2) | 2.662 (2) | 176 (3) |
Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x−1, y, z; (iv) x, −y+3/2, z−1/2; (v) x, −y+3/2, z+1/2; (vi) −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