Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040384/wm2049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040384/wm2049Isup2.hkl |
CCDC reference: 277581
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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, 2001); software used to prepare material for publication: SHELXTL.
C4H7N2+·B5H4O10− | F(000) = 616 |
Mr = 301.20 | Dx = 1.473 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1799 reflections |
a = 8.4513 (16) Å | θ = 2.3–23.7° |
b = 11.458 (2) Å | µ = 0.13 mm−1 |
c = 14.026 (3) Å | T = 293 K |
β = 90.682 (4)° | Column, colorless |
V = 1358.2 (4) Å3 | 0.22 × 0.17 × 0.12 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 2676 independent reflections |
Radiation source: fine-focus sealed tube | 1878 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1999) | h = −10→7 |
Tmin = 0.971, Tmax = 0.984 | k = −14→12 |
7450 measured reflections | l = −17→17 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0682P)2 + 0.3185P] where P = (Fo2 + 2Fc2)/3 |
2676 reflections | (Δ/σ)max = 0.005 |
195 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
Experimental. The chemical composition of the crystals was determined for C, H, N by elemental analysis using a Vario EL III Elemental Analyzer, and for B by titration of a NaOH standard solution in the presence of mannitol. IR spectroscopic measurements (Nicolet NEXUS 670 spectrometer using KBr pellets at room temperature) Thermogravimetry (TG) and differential thermal analysis (DTA) (Universal V4.one-dimensional TA-SDT Q600 thermal analyzer in air, heating rate 10?K?min1) |
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 | 0.44188 (16) | −0.06890 (12) | 0.25202 (10) | 0.0453 (4) | |
O2 | 0.47233 (16) | 0.13956 (12) | 0.23470 (10) | 0.0454 (4) | |
O3 | 0.61630 (19) | 0.03610 (12) | 0.35396 (11) | 0.0561 (5) | |
O4 | 0.6078 (2) | −0.16586 (13) | 0.36318 (13) | 0.0652 (5) | |
H4 | 0.5769 | −0.2227 | 0.3327 | 0.098* | |
O5 | 0.6518 (2) | 0.23582 (13) | 0.33873 (13) | 0.0662 (5) | |
H5 | 0.6235 | 0.2915 | 0.3060 | 0.099* | |
O6 | 0.21499 (16) | 0.05309 (13) | 0.22935 (10) | 0.0470 (4) | |
O7 | 0.39844 (16) | 0.02207 (12) | 0.10148 (10) | 0.0428 (4) | |
O8 | 0.12344 (18) | 0.01392 (19) | 0.07322 (11) | 0.0707 (6) | |
O9 | −0.05589 (18) | 0.05788 (18) | 0.19528 (11) | 0.0632 (5) | |
H9 | −0.1167 | 0.0485 | 0.1499 | 0.095* | |
O10 | 0.29385 (19) | −0.02364 (19) | −0.05142 (11) | 0.0697 (6) | |
H10 | 0.3886 | −0.0293 | −0.0625 | 0.104* | |
N1 | −0.1140 (3) | 0.1843 (2) | 0.4730 (2) | 0.0841 (8) | |
H1A | −0.1776 | 0.2051 | 0.4296 | 0.101* | |
N2 | 0.0958 (3) | 0.1575 (2) | 0.55155 (17) | 0.0777 (8) | |
H2A | 0.1937 | 0.1620 | 0.5774 | 0.093* | |
B1 | 0.3787 (3) | 0.0372 (2) | 0.20454 (17) | 0.0394 (6) | |
B2 | 0.5533 (3) | −0.0669 (2) | 0.32113 (18) | 0.0447 (6) | |
B3 | 0.5781 (3) | 0.1379 (2) | 0.30746 (18) | 0.0451 (6) | |
B4 | 0.0953 (3) | 0.0425 (2) | 0.16624 (18) | 0.0439 (6) | |
B5 | 0.2740 (3) | 0.0040 (2) | 0.04178 (18) | 0.0482 (7) | |
C1 | 0.0372 (3) | 0.1985 (2) | 0.47304 (19) | 0.0632 (7) | |
C2 | −0.1553 (5) | 0.1301 (4) | 0.5578 (3) | 0.1156 (14) | |
H2 | −0.2568 | 0.1099 | 0.5765 | 0.139* | |
C3 | −0.0250 (5) | 0.1130 (4) | 0.6057 (3) | 0.1135 (14) | |
H3 | −0.0151 | 0.0775 | 0.6651 | 0.136* | |
C4 | 0.1276 (5) | 0.2502 (3) | 0.3953 (2) | 0.1124 (14) | |
H4A | 0.0901 | 0.2197 | 0.3354 | 0.169* | |
H4B | 0.2377 | 0.2315 | 0.4035 | 0.169* | |
H4C | 0.1145 | 0.3334 | 0.3959 | 0.169* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0484 (9) | 0.0328 (8) | 0.0541 (9) | −0.0019 (6) | −0.0281 (7) | 0.0005 (6) |
O2 | 0.0489 (9) | 0.0338 (8) | 0.0526 (9) | −0.0011 (6) | −0.0288 (7) | 0.0006 (6) |
O3 | 0.0682 (11) | 0.0357 (9) | 0.0634 (10) | −0.0023 (7) | −0.0432 (8) | 0.0011 (7) |
O4 | 0.0797 (12) | 0.0361 (9) | 0.0784 (12) | −0.0012 (8) | −0.0538 (9) | 0.0028 (8) |
O5 | 0.0777 (12) | 0.0355 (9) | 0.0839 (12) | −0.0026 (8) | −0.0568 (10) | 0.0002 (8) |
O6 | 0.0410 (8) | 0.0567 (10) | 0.0430 (8) | 0.0042 (7) | −0.0172 (6) | −0.0054 (7) |
O7 | 0.0353 (8) | 0.0496 (9) | 0.0432 (8) | 0.0000 (6) | −0.0170 (6) | −0.0039 (7) |
O8 | 0.0339 (9) | 0.1317 (17) | 0.0461 (10) | 0.0019 (9) | −0.0162 (7) | −0.0189 (10) |
O9 | 0.0417 (9) | 0.0972 (14) | 0.0505 (10) | 0.0069 (9) | −0.0153 (7) | −0.0092 (9) |
O10 | 0.0375 (9) | 0.1253 (17) | 0.0458 (10) | 0.0014 (10) | −0.0168 (7) | −0.0180 (10) |
N1 | 0.0694 (16) | 0.0848 (18) | 0.0969 (19) | 0.0024 (13) | −0.0501 (14) | −0.0016 (15) |
N2 | 0.0753 (16) | 0.0759 (16) | 0.0808 (17) | 0.0073 (13) | −0.0476 (14) | −0.0007 (13) |
B1 | 0.0406 (13) | 0.0349 (13) | 0.0423 (13) | 0.0005 (10) | −0.0197 (10) | −0.0016 (10) |
B2 | 0.0470 (14) | 0.0380 (13) | 0.0484 (14) | 0.0008 (10) | −0.0235 (11) | −0.0001 (11) |
B3 | 0.0472 (14) | 0.0345 (13) | 0.0529 (14) | 0.0018 (10) | −0.0245 (11) | −0.0020 (11) |
B4 | 0.0385 (13) | 0.0493 (15) | 0.0437 (14) | 0.0024 (10) | −0.0137 (10) | −0.0007 (11) |
B5 | 0.0371 (14) | 0.0635 (17) | 0.0435 (14) | −0.0005 (11) | −0.0167 (11) | −0.0039 (12) |
C1 | 0.0733 (18) | 0.0504 (15) | 0.0653 (16) | 0.0045 (13) | −0.0259 (14) | −0.0073 (12) |
C2 | 0.082 (3) | 0.141 (4) | 0.124 (3) | −0.029 (2) | 0.001 (2) | 0.025 (3) |
C3 | 0.137 (4) | 0.131 (4) | 0.072 (2) | −0.033 (3) | −0.027 (2) | 0.030 (2) |
C4 | 0.168 (4) | 0.078 (2) | 0.093 (3) | −0.010 (2) | 0.048 (3) | −0.011 (2) |
B1—O1 | 1.482 (3) | O4—H4 | 0.82 |
B1—O2 | 1.474 (3) | O5—H5 | 0.82 |
B1—O6 | 1.442 (3) | O10—H10 | 0.82 |
B1—O7 | 1.467 (3) | N1—C1 | 1.288 (3) |
B2—O3 | 1.372 (3) | N1—C2 | 1.389 (5) |
B2—O1 | 1.344 (2) | N1—H1A | 0.84 |
B2—O4 | 1.356 (3) | N2—C1 | 1.291 (3) |
B3—O3 | 1.373 (3) | N2—C3 | 1.377 (4) |
B3—O2 | 1.349 (2) | N2—H2A | 0.90 |
B3—O5 | 1.354 (3) | C1—C4 | 1.464 (4) |
B4—O6 | 1.342 (3) | C2—C3 | 1.298 (5) |
B4—O8 | 1.369 (3) | C2—H2 | 0.93 |
B4—O9 | 1.357 (3) | C3—H3 | 0.93 |
B5—O7 | 1.352 (3) | C4—H4A | 0.96 |
B5—O8 | 1.357 (3) | C4—H4B | 0.96 |
B5—O10 | 1.357 (3) | C4—H4C | 0.96 |
O9—H9 | 0.82 | ||
B2—O1—B1 | 123.76 (16) | O2—B3—O5 | 122.1 (2) |
B3—O2—B1 | 123.67 (17) | O2—B3—O3 | 121.43 (19) |
B2—O3—B3 | 118.89 (17) | O5—B3—O3 | 116.45 (18) |
B2—O4—H4 | 109.5 | O6—B4—O9 | 119.7 (2) |
B3—O5—H5 | 109.5 | O6—B4—O8 | 120.8 (2) |
B4—O6—B1 | 123.17 (18) | O9—B4—O8 | 119.47 (18) |
B5—O7—B1 | 122.11 (18) | O7—B5—O10 | 121.9 (2) |
B5—O8—B4 | 120.28 (18) | O7—B5—O8 | 120.8 (2) |
B4—O9—H9 | 109.5 | O10—B5—O8 | 117.36 (19) |
B5—O10—H10 | 109.5 | N1—C1—N2 | 108.9 (3) |
C1—N1—C2 | 108.4 (2) | N1—C1—C4 | 125.3 (3) |
C1—N1—H1A | 126.1 | N2—C1—C4 | 125.8 (3) |
C2—N1—H1A | 125.5 | C3—C2—N1 | 106.9 (3) |
C1—N2—C3 | 109.0 (3) | C3—C2—H2 | 126.6 |
C1—N2—H2A | 131.6 | N1—C2—H2 | 126.6 |
C3—N2—H2A | 118.8 | C2—C3—N2 | 106.7 (3) |
O6—B1—O7 | 111.92 (15) | C2—C3—H3 | 126.6 |
O6—B1—O2 | 110.07 (17) | N2—C3—H3 | 126.6 |
O7—B1—O2 | 108.03 (18) | C1—C4—H4A | 109.5 |
O6—B1—O1 | 109.68 (18) | C1—C4—H4B | 109.5 |
O7—B1—O1 | 107.54 (17) | H4A—C4—H4B | 109.5 |
O2—B1—O1 | 109.53 (15) | C1—C4—H4C | 109.5 |
O1—B2—O4 | 122.06 (19) | H4A—C4—H4C | 109.5 |
O1—B2—O3 | 121.51 (19) | H4B—C4—H4C | 109.5 |
O4—B2—O3 | 116.43 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O5i | 0.84 | 1.95 | 2.780 (2) | 170.8 |
N2—H2A···O4ii | 0.90 | 1.87 | 2.765 (3) | 176.6 |
O4—H4···O2iii | 0.82 | 1.88 | 2.700 (2) | 174 |
O5—H5···O1iv | 0.82 | 1.87 | 2.689 (2) | 172 |
O9—H9···O10v | 0.82 | 2.05 | 2.859 (2) | 172 |
O10—H10···O7vi | 0.82 | 1.89 | 2.702 (2) | 171 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2; (v) −x, −y, −z; (vi) −x+1, −y, −z. |