Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027158/gw2009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027158/gw2009Isup2.hkl |
CCDC reference: 654935
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.032
- wR factor = 0.084
- Data-to-parameter ratio = 11.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.26 Deg.
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5556 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 23.26 Deg.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.24 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.241 Tmax scaled 0.695 Tmin scaled 0.292 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 23.26 From the CIF: _reflns_number_total 1461 Count of symmetry unique reflns 807 Completeness (_total/calc) 181.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 654 Fraction of Friedel pairs measured 0.810 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Bruker–Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).
C6H12BN2O4+·Br− | Z = 1 |
Mr = 266.89 | F(000) = 134 |
Triclinic, P1 | Dx = 1.571 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5806 (3) Å | Cell parameters from 770 reflections |
b = 6.0026 (4) Å | θ = 1.0–23.3° |
c = 9.7951 (6) Å | µ = 3.64 mm−1 |
α = 98.823 (3)° | T = 293 K |
β = 97.302 (4)° | Parallelepiped, colourless |
γ = 116.858 (3)° | 0.35 × 0.30 × 0.10 mm |
V = 281.99 (3) Å3 |
Nonius KappaCCD diffractometer | 1461 independent reflections |
Radiation source: fine-focus sealed tube | 1452 reflections with I > 2σ(I) |
Horizontally mounted graphite monochromator | Rint = 0.037 |
Detector resolution: 9 pixels mm-1 | θmax = 23.3°, θmin = 3.9° |
CCD scans | h = −6→5 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)' | k = −6→6 |
Tmin = 0.235, Tmax = 0.560 | l = −10→10 |
2416 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0605P)2 + 0.06P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.54 e Å−3 |
1461 reflections | Δρmin = −0.41 e Å−3 |
128 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.105 (18) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 654 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.016 (10) |
Experimental. Crystals suitable for X-ray diffraction were difficult to obtain. |
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 | ||
Br1 | 0.0000 (1) | 0.0000 (1) | 0.0000 (1) | 0.0536 (3) | |
B1 | 0.9166 (11) | 0.5722 (10) | 0.5161 (6) | 0.0340 (11) | |
O1 | 1.1940 (7) | 0.8210 (6) | 0.5553 (3) | 0.0369 (7) | |
N1 | 1.5901 (8) | 1.0019 (7) | 0.7207 (4) | 0.0378 (9) | |
H1A | 1.6637 | 1.1289 | 0.6819 | 0.045* | |
H1B | 1.6826 | 0.9953 | 0.7958 | 0.045* | |
C1 | 1.3411 (9) | 0.8215 (8) | 0.6664 (5) | 0.0303 (9) | |
O2 | 0.9316 (7) | 0.4541 (6) | 0.6301 (4) | 0.0409 (8) | |
C2 | 1.1904 (11) | 0.5898 (9) | 0.7254 (6) | 0.0323 (12) | |
H2 | 1.1657 | 0.6477 | 0.8192 | 0.039* | |
C3 | 1.3359 (11) | 0.4324 (10) | 0.7379 (7) | 0.0477 (13) | |
H3A | 1.2301 | 0.2893 | 0.7760 | 0.072* | |
H3B | 1.5148 | 0.5374 | 0.7997 | 0.072* | |
H3C | 1.3554 | 0.3702 | 0.6459 | 0.072* | |
O4 | 0.9170 (8) | 0.4220 (7) | 0.3746 (4) | 0.0401 (8) | |
N4 | 0.6573 (10) | 0.2649 (10) | 0.1522 (5) | 0.0505 (11) | |
H4A | 0.7604 | 0.2030 | 0.1253 | 0.061* | |
H4B | 0.5180 | 0.2449 | 0.0925 | 0.061* | |
C4 | 0.7114 (10) | 0.3868 (10) | 0.2812 (6) | 0.0349 (12) | |
O5 | 0.6855 (7) | 0.6083 (7) | 0.4855 (4) | 0.0428 (8) | |
C5 | 0.5472 (10) | 0.5054 (9) | 0.3407 (5) | 0.0350 (10) | |
H5 | 0.3590 | 0.3699 | 0.3332 | 0.042* | |
C6 | 0.5376 (15) | 0.7039 (13) | 0.2693 (7) | 0.0606 (16) | |
H6A | 0.4290 | 0.7703 | 0.3107 | 0.091* | |
H6B | 0.4564 | 0.6282 | 0.1701 | 0.091* | |
H6C | 0.7212 | 0.8414 | 0.2809 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0425 (3) | 0.0736 (4) | 0.0443 (3) | 0.0312 (3) | 0.00584 (19) | 0.0058 (2) |
B1 | 0.025 (3) | 0.040 (3) | 0.034 (3) | 0.014 (2) | 0.004 (2) | 0.007 (2) |
O1 | 0.0327 (18) | 0.0286 (15) | 0.0426 (18) | 0.0082 (14) | 0.0065 (14) | 0.0127 (13) |
N1 | 0.032 (2) | 0.0293 (19) | 0.043 (2) | 0.0070 (17) | 0.0039 (17) | 0.0122 (17) |
C1 | 0.032 (2) | 0.025 (2) | 0.031 (2) | 0.0125 (19) | 0.0070 (19) | 0.0062 (18) |
O2 | 0.0264 (18) | 0.0354 (17) | 0.049 (2) | 0.0044 (14) | 0.0035 (15) | 0.0158 (16) |
C2 | 0.025 (3) | 0.031 (2) | 0.040 (3) | 0.011 (2) | 0.009 (2) | 0.012 (2) |
C3 | 0.037 (3) | 0.042 (3) | 0.070 (4) | 0.018 (2) | 0.015 (3) | 0.027 (3) |
O4 | 0.0262 (19) | 0.0428 (19) | 0.048 (2) | 0.0171 (16) | 0.0057 (16) | 0.0019 (16) |
N4 | 0.043 (2) | 0.071 (3) | 0.039 (2) | 0.035 (2) | −0.0018 (19) | 0.000 (2) |
C4 | 0.023 (3) | 0.037 (2) | 0.038 (3) | 0.012 (2) | −0.002 (2) | 0.004 (2) |
O5 | 0.0380 (19) | 0.055 (2) | 0.0380 (18) | 0.0281 (16) | 0.0058 (15) | 0.0027 (15) |
C5 | 0.026 (2) | 0.045 (3) | 0.039 (3) | 0.019 (2) | 0.010 (2) | 0.011 (2) |
C6 | 0.072 (4) | 0.065 (3) | 0.075 (4) | 0.048 (3) | 0.032 (3) | 0.037 (3) |
B1—O5 | 1.405 (7) | C3—H3B | 0.9600 |
B1—O2 | 1.425 (7) | C3—H3C | 0.9600 |
B1—O4 | 1.534 (6) | O4—C4 | 1.286 (7) |
B1—O1 | 1.536 (6) | N4—C4 | 1.282 (8) |
O1—C1 | 1.275 (6) | N4—H4A | 0.8600 |
N1—C1 | 1.289 (6) | N4—H4B | 0.8600 |
N1—H1A | 0.8600 | C4—C5 | 1.512 (8) |
N1—H1B | 0.8600 | O5—C5 | 1.418 (6) |
C1—C2 | 1.514 (7) | C5—C6 | 1.489 (8) |
O2—C2 | 1.408 (7) | C5—H5 | 0.9800 |
C2—C3 | 1.506 (8) | C6—H6A | 0.9600 |
C2—H2 | 0.9800 | C6—H6B | 0.9600 |
C3—H3A | 0.9600 | C6—H6C | 0.9600 |
O5—B1—O2 | 116.8 (4) | C2—C3—H3C | 109.5 |
O5—B1—O4 | 104.2 (4) | H3A—C3—H3C | 109.5 |
O2—B1—O4 | 113.1 (4) | H3B—C3—H3C | 109.5 |
O5—B1—O1 | 114.4 (4) | C4—O4—B1 | 108.2 (4) |
O2—B1—O1 | 103.1 (4) | C4—N4—H4A | 120.0 |
O4—B1—O1 | 104.8 (4) | C4—N4—H4B | 120.0 |
C1—O1—B1 | 108.9 (3) | H4A—N4—H4B | 120.0 |
C1—N1—H1A | 120.0 | N4—C4—O4 | 122.5 (5) |
C1—N1—H1B | 120.0 | N4—C4—C5 | 124.9 (5) |
H1A—N1—H1B | 120.0 | O4—C4—C5 | 112.6 (5) |
O1—C1—N1 | 122.8 (4) | B1—O5—C5 | 112.4 (4) |
O1—C1—C2 | 112.5 (4) | O5—C5—C6 | 112.7 (5) |
N1—C1—C2 | 124.7 (4) | O5—C5—C4 | 102.5 (4) |
C2—O2—B1 | 112.4 (4) | C6—C5—C4 | 113.4 (4) |
O2—C2—C3 | 113.2 (4) | O5—C5—H5 | 109.4 |
O2—C2—C1 | 102.7 (4) | C6—C5—H5 | 109.4 |
C3—C2—C1 | 113.7 (4) | C4—C5—H5 | 109.4 |
O2—C2—H2 | 109.0 | C5—C6—H6A | 109.5 |
C3—C2—H2 | 109.0 | C5—C6—H6B | 109.5 |
C1—C2—H2 | 109.0 | H6A—C6—H6B | 109.5 |
C2—C3—H3A | 109.5 | C5—C6—H6C | 109.5 |
C2—C3—H3B | 109.5 | H6A—C6—H6C | 109.5 |
H3A—C3—H3B | 109.5 | H6B—C6—H6C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4B···Br1 | 0.86 | 2.53 | 3.289 (5) | 147 |
N1—H1A···O2i | 0.86 | 2.04 | 2.878 (5) | 164 |
N1—H1B···Br1ii | 0.86 | 2.49 | 3.341 (4) | 173 |
N4—H4A···Br1iii | 0.86 | 2.49 | 3.339 (5) | 169 |
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z+1; (iii) x+1, y, z. |
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