Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032235/om2050sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032235/om2050Isup2.hkl |
CCDC reference: 624964
Data collection: FRAMBO (Bruker–Nonius, 2003); cell refinement: Cell_Now (Sheldrick, 2003) and SAINT (Bruker–Nonius, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2001); program(s) used to refine structure: SHELXL97 (Sheldrick, 2001); molecular graphics: X-SEED (Barbour, 2001) and DIAMOND (Brandenbourg, 2001); software used to prepare material for publication: SHELXL97, PLATON (Spek 2004) as incorporated in WinGX (Farrugia, 1999)'.
C13H15BF2N2 | F(000) = 520 |
Mr = 248.08 | Dx = 1.353 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 7.6932 (13) Å | Cell parameters from 739 reflections |
b = 14.379 (2) Å | θ = 5.1–51.4° |
c = 11.5295 (16) Å | µ = 0.84 mm−1 |
β = 107.245 (8)° | T = 110 K |
V = 1218.0 (3) Å3 | Block, red |
Z = 4 | 0.08 × 0.03 × 0.01 mm |
Bruker GADDS D8 Discover diffractometer | 1736 independent reflections |
Radiation source: fine-focus sealed tube | 1035 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.085 |
φ and ω scans | θmax = 59.5°, θmin = 5.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −8→8 |
Tmin = 0.936, Tmax = 0.992 | k = −16→16 |
7569 measured reflections | l = −12→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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.06 | w = [exp{2(sinθ/λ)2}]/[σ2(Fo2) + (0.061P)2]
where P = 0.333Fo2 + 0.667Fc2 |
1736 reflections | (Δ/σ)max < 0.001 |
167 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Experimental. For data collection a BRUKER GADDS D8 Discover instrument equipped with a combination of monochromated (with Graphite) CuKα radiation, and a HI-STAR multi-wire proportional counter area detector was used. |
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 | 0.0294 (5) | 0.4137 (3) | 0.7772 (3) | 0.0294 (9) | |
F1 | −0.1296 (2) | 0.36472 (11) | 0.77587 (15) | 0.0360 (5) | |
F2 | 0.0918 (2) | 0.38121 (12) | 0.68269 (14) | 0.0369 (5) | |
N1 | 0.1754 (3) | 0.39915 (16) | 0.9023 (2) | 0.0266 (6) | |
N2 | −0.0104 (3) | 0.51964 (16) | 0.7635 (2) | 0.0261 (6) | |
C1 | 0.2589 (4) | 0.3182 (2) | 0.9488 (3) | 0.0287 (8) | |
C2 | 0.3815 (4) | 0.3355 (2) | 1.0637 (3) | 0.0322 (8) | |
H7 | 0.4563 | 0.2904 | 1.1154 | 0.039* | |
C3 | 0.3752 (4) | 0.4301 (2) | 1.0892 (3) | 0.0290 (8) | |
C4 | 0.2465 (4) | 0.4700 (2) | 0.9868 (3) | 0.0266 (7) | |
C5 | 0.1875 (4) | 0.5613 (2) | 0.9625 (3) | 0.0250 (7) | |
H5 | 0.2339 | 0.6076 | 1.0226 | 0.030* | |
C6 | 0.0637 (4) | 0.5869 (2) | 0.8537 (2) | 0.0248 (7) | |
C7 | −0.0115 (4) | 0.6745 (2) | 0.8098 (3) | 0.0287 (8) | |
C8 | −0.1277 (4) | 0.6598 (2) | 0.6946 (3) | 0.0310 (8) | |
H2 | −0.1973 | 0.7062 | 0.6424 | 0.037* | |
C9 | −0.1254 (4) | 0.5642 (2) | 0.6676 (3) | 0.0286 (8) | |
C10 | 0.2156 (5) | 0.2276 (2) | 0.8843 (3) | 0.0370 (8) | |
H12A | 0.0846 | 0.2156 | 0.8645 | 0.055* | |
H12B | 0.2829 | 0.1778 | 0.9366 | 0.055* | |
H12C | 0.2507 | 0.2299 | 0.8093 | 0.055* | |
C11 | 0.4836 (4) | 0.4812 (2) | 1.2015 (3) | 0.0337 (8) | |
H11A | 0.4194 | 0.4783 | 1.2632 | 0.051* | |
H11B | 0.4982 | 0.5463 | 1.1811 | 0.051* | |
H11C | 0.6037 | 0.4522 | 1.2332 | 0.051* | |
C12 | 0.0327 (5) | 0.7657 (2) | 0.8769 (3) | 0.0346 (8) | |
H10A | 0.1446 | 0.7914 | 0.8658 | 0.052* | |
H10B | 0.0498 | 0.7553 | 0.9636 | 0.052* | |
H10C | −0.0677 | 0.8095 | 0.8450 | 0.052* | |
C13 | −0.2291 (4) | 0.5161 (2) | 0.5535 (3) | 0.0354 (8) | |
H9A | −0.1503 | 0.5075 | 0.5013 | 0.053* | |
H9B | −0.3347 | 0.5539 | 0.5108 | 0.053* | |
H9C | −0.2704 | 0.4553 | 0.5734 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
B1 | 0.032 (2) | 0.032 (2) | 0.0245 (19) | −0.0053 (17) | 0.0084 (17) | −0.0017 (16) |
F1 | 0.0328 (11) | 0.0334 (10) | 0.0398 (10) | −0.0079 (8) | 0.0075 (8) | −0.0011 (9) |
F2 | 0.0455 (12) | 0.0390 (11) | 0.0266 (9) | 0.0049 (9) | 0.0111 (8) | −0.0029 (8) |
N1 | 0.0264 (14) | 0.0295 (15) | 0.0247 (13) | −0.0035 (12) | 0.0088 (12) | 0.0006 (12) |
N2 | 0.0239 (14) | 0.0285 (15) | 0.0253 (14) | −0.0023 (11) | 0.0061 (12) | −0.0005 (11) |
C1 | 0.0304 (19) | 0.0277 (19) | 0.0296 (18) | 0.0024 (14) | 0.0116 (16) | 0.0047 (14) |
C2 | 0.0319 (19) | 0.033 (2) | 0.0297 (18) | 0.0034 (15) | 0.0063 (16) | 0.0074 (14) |
C3 | 0.0266 (18) | 0.034 (2) | 0.0292 (18) | −0.0054 (14) | 0.0129 (15) | 0.0028 (14) |
C4 | 0.0233 (17) | 0.0336 (19) | 0.0229 (16) | −0.0043 (14) | 0.0066 (14) | 0.0022 (14) |
C5 | 0.0242 (17) | 0.0283 (18) | 0.0255 (16) | −0.0058 (13) | 0.0117 (15) | −0.0022 (13) |
C6 | 0.0216 (17) | 0.0286 (17) | 0.0261 (17) | −0.0030 (14) | 0.0100 (14) | −0.0018 (14) |
C7 | 0.0261 (18) | 0.0282 (18) | 0.0319 (18) | −0.0035 (14) | 0.0089 (15) | 0.0013 (14) |
C8 | 0.0300 (19) | 0.0324 (19) | 0.0292 (18) | 0.0023 (15) | 0.0064 (16) | 0.0070 (14) |
C9 | 0.0210 (17) | 0.037 (2) | 0.0300 (18) | −0.0030 (14) | 0.0109 (15) | 0.0036 (14) |
C10 | 0.045 (2) | 0.0309 (19) | 0.0346 (19) | −0.0001 (17) | 0.0118 (17) | 0.0016 (15) |
C11 | 0.0332 (19) | 0.039 (2) | 0.0271 (17) | −0.0020 (16) | 0.0059 (15) | 0.0008 (15) |
C12 | 0.036 (2) | 0.0280 (18) | 0.0389 (19) | −0.0006 (15) | 0.0091 (17) | −0.0024 (15) |
C13 | 0.035 (2) | 0.041 (2) | 0.0273 (18) | −0.0008 (16) | 0.0038 (16) | 0.0016 (15) |
B1—F2 | 1.395 (4) | C7—C8 | 1.379 (4) |
B1—F1 | 1.407 (4) | C7—C12 | 1.508 (4) |
B1—N2 | 1.553 (4) | C8—C9 | 1.411 (4) |
B1—N1 | 1.557 (4) | C8—H2 | 0.9500 |
N1—C1 | 1.360 (4) | C9—C13 | 1.492 (4) |
N1—C4 | 1.403 (4) | C10—H12A | 0.9800 |
N2—C9 | 1.354 (4) | C10—H12B | 0.9800 |
N2—C6 | 1.411 (4) | C10—H12C | 0.9800 |
C1—C2 | 1.401 (4) | C11—H11A | 0.9800 |
C1—C10 | 1.488 (4) | C11—H11B | 0.9800 |
C2—C3 | 1.396 (4) | C11—H11C | 0.9800 |
C2—H7 | 0.9500 | C12—H10A | 0.9800 |
C3—C4 | 1.418 (4) | C12—H10B | 0.9800 |
C3—C11 | 1.507 (4) | C12—H10C | 0.9800 |
C4—C5 | 1.390 (4) | C13—H9A | 0.9800 |
C5—C6 | 1.381 (4) | C13—H9B | 0.9800 |
C5—H5 | 0.9500 | C13—H9C | 0.9800 |
C6—C7 | 1.416 (4) | ||
F2—B1—F1 | 108.9 (3) | C6—C7—C12 | 125.7 (3) |
F2—B1—N2 | 110.6 (3) | C7—C8—C9 | 108.3 (3) |
F1—B1—N2 | 110.2 (3) | C7—C8—H2 | 125.8 |
F2—B1—N1 | 111.0 (3) | C9—C8—H2 | 125.8 |
F1—B1—N1 | 109.2 (2) | N2—C9—C8 | 109.2 (3) |
N2—B1—N1 | 107.0 (2) | N2—C9—C13 | 123.3 (3) |
C1—N1—C4 | 107.8 (2) | C8—C9—C13 | 127.5 (3) |
C1—N1—B1 | 127.3 (2) | C1—C10—H12A | 109.5 |
C4—N1—B1 | 124.8 (2) | C1—C10—H12B | 109.5 |
C9—N2—C6 | 107.5 (2) | H12A—C10—H12B | 109.5 |
C9—N2—B1 | 127.5 (2) | C1—C10—H12C | 109.5 |
C6—N2—B1 | 124.9 (2) | H12A—C10—H12C | 109.5 |
N1—C1—C2 | 109.2 (3) | H12B—C10—H12C | 109.5 |
N1—C1—C10 | 122.8 (3) | C3—C11—H11A | 109.5 |
C2—C1—C10 | 128.0 (3) | C3—C11—H11B | 109.5 |
C3—C2—C1 | 108.4 (3) | H11A—C11—H11B | 109.5 |
C3—C2—H7 | 125.8 | C3—C11—H11C | 109.5 |
C1—C2—H7 | 125.8 | H11A—C11—H11C | 109.5 |
C2—C3—C4 | 106.1 (3) | H11B—C11—H11C | 109.5 |
C2—C3—C11 | 127.7 (3) | C7—C12—H10A | 109.5 |
C4—C3—C11 | 126.2 (3) | C7—C12—H10B | 109.5 |
C5—C4—N1 | 120.6 (3) | H10A—C12—H10B | 109.5 |
C5—C4—C3 | 130.9 (3) | C7—C12—H10C | 109.5 |
N1—C4—C3 | 108.4 (2) | H10A—C12—H10C | 109.5 |
C6—C5—C4 | 122.0 (3) | H10B—C12—H10C | 109.5 |
C6—C5—H5 | 119.0 | C9—C13—H9A | 109.5 |
C4—C5—H5 | 119.0 | C9—C13—H9B | 109.5 |
C5—C6—N2 | 120.4 (3) | H9A—C13—H9B | 109.5 |
C5—C6—C7 | 131.3 (3) | C9—C13—H9C | 109.5 |
N2—C6—C7 | 108.2 (2) | H9A—C13—H9C | 109.5 |
C8—C7—C6 | 106.7 (3) | H9B—C13—H9C | 109.5 |
C8—C7—C12 | 127.6 (3) | ||
F2—B1—N1—C1 | −54.9 (4) | C2—C3—C4—C5 | −179.4 (3) |
F1—B1—N1—C1 | 65.1 (4) | C11—C3—C4—C5 | 0.0 (5) |
N2—B1—N1—C1 | −175.6 (3) | C2—C3—C4—N1 | 0.9 (3) |
F2—B1—N1—C4 | 123.8 (3) | C11—C3—C4—N1 | −179.8 (3) |
F1—B1—N1—C4 | −116.1 (3) | N1—C4—C5—C6 | −2.7 (4) |
N2—B1—N1—C4 | 3.1 (4) | C3—C4—C5—C6 | 177.6 (3) |
F2—B1—N2—C9 | 57.4 (4) | C4—C5—C6—N2 | 1.2 (4) |
F1—B1—N2—C9 | −63.0 (4) | C4—C5—C6—C7 | −178.8 (3) |
N1—B1—N2—C9 | 178.4 (3) | C9—N2—C6—C5 | −179.6 (3) |
F2—B1—N2—C6 | −125.6 (3) | B1—N2—C6—C5 | 2.9 (4) |
F1—B1—N2—C6 | 114.0 (3) | C9—N2—C6—C7 | 0.4 (3) |
N1—B1—N2—C6 | −4.6 (4) | B1—N2—C6—C7 | −177.1 (3) |
C4—N1—C1—C2 | 1.0 (3) | C5—C6—C7—C8 | 179.6 (3) |
B1—N1—C1—C2 | 179.9 (3) | N2—C6—C7—C8 | −0.4 (3) |
C4—N1—C1—C10 | 179.2 (3) | C5—C6—C7—C12 | 0.7 (5) |
B1—N1—C1—C10 | −1.9 (5) | N2—C6—C7—C12 | −179.2 (3) |
N1—C1—C2—C3 | −0.4 (3) | C6—C7—C8—C9 | 0.3 (3) |
C10—C1—C2—C3 | −178.6 (3) | C12—C7—C8—C9 | 179.1 (3) |
C1—C2—C3—C4 | −0.3 (3) | C6—N2—C9—C8 | −0.2 (3) |
C1—C2—C3—C11 | −179.7 (3) | B1—N2—C9—C8 | 177.2 (3) |
C1—N1—C4—C5 | 179.1 (3) | C6—N2—C9—C13 | 179.5 (3) |
B1—N1—C4—C5 | 0.2 (4) | B1—N2—C9—C13 | −3.1 (5) |
C1—N1—C4—C3 | −1.1 (3) | C7—C8—C9—N2 | 0.0 (4) |
B1—N1—C4—C3 | 179.9 (3) | C7—C8—C9—C13 | −179.8 (3) |