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
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.119
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 59.48 Deg.
Author Response: We have used a combination of CuK\a radiation along with multiwire proportional counter. Thus the instrumental geometry restricts the maximum theta angle to theta = 60 degrees. |
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5587 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 59.48 Deg.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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) |
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