Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016904/sg2024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016904/sg2024Isup2.hkl |
CCDC reference: 610884
Data collection: SMART (Bruker,1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; 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.
C8H7Br3N2O3 | F(000) = 396 |
Mr = 418.89 | Dx = 2.278 Mg m−3 |
Triclinic, P1 | Melting point: 481 K |
a = 7.0199 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.0368 (12) Å | Cell parameters from 2129 reflections |
c = 11.5897 (16) Å | θ = 2.6–25.9° |
α = 97.019 (2)° | µ = 9.90 mm−1 |
β = 103.741 (2)° | T = 273 K |
γ = 102.156 (2)° | Block, colorless |
V = 610.61 (15) Å3 | 0.34 × 0.29 × 0.26 mm |
Z = 2 |
Bruker SMART 1K CCD area-detector diffractometer | 2328 independent reflections |
Radiation source: fine-focus sealed tube | 1837 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 26.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick,1996) | h = −8→8 |
Tmin = 0.050, Tmax = 0.072 | k = −9→9 |
4506 measured reflections | l = −14→14 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0605P)2 + 0.8415P] where P = (Fo2 + 2Fc2)/3 |
2328 reflections | (Δ/σ)max = 0.001 |
146 parameters | Δρmax = 0.80 e Å−3 |
0 restraints | Δρmin = −0.81 e Å−3 |
Experimental. 1H NMR (DMSO6, 300 Hz): δ 12.61 (brs, 1H), 12.22 (brs, 1H), 8.13 (t, 1H), 3.49–3.35 (m, 2H), 2.46 (t, 2H); IR (KBr): 3401, 2929, 1698, 1638, 1551, 1511, 1426, 1243, 778; Analysis calculated for C8H7Br3N2O3: C 22.94, H 1.68, N 6.69%; found C 22.85, H 1.74, N 6.87.% |
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 | 0.18695 (9) | 0.14910 (9) | 0.92476 (6) | 0.0529 (2) | |
Br2 | 0.37542 (9) | 0.08757 (8) | 1.22695 (5) | 0.0484 (2) | |
Br3 | 0.90944 (9) | 0.29884 (10) | 1.32263 (5) | 0.0570 (2) | |
N1 | 0.7846 (6) | 0.3519 (5) | 1.0826 (4) | 0.0338 (10) | |
H1 | 0.9052 | 0.4082 | 1.0864 | 0.041* | |
C3 | 0.4575 (7) | 0.2267 (6) | 1.0165 (4) | 0.0292 (10) | |
C4 | 0.6208 (7) | 0.3218 (6) | 0.9845 (4) | 0.0314 (10) | |
C1 | 0.7286 (8) | 0.2799 (7) | 1.1724 (4) | 0.0364 (12) | |
C2 | 0.5276 (7) | 0.2024 (6) | 1.1357 (5) | 0.0333 (11) | |
N2 | 0.4886 (6) | 0.3699 (5) | 0.7844 (4) | 0.0349 (10) | |
H2 | 0.3707 | 0.3282 | 0.7932 | 0.042* | |
O1 | 0.8225 (6) | 0.4464 (6) | 0.8691 (4) | 0.0533 (11) | |
C5 | 0.6516 (7) | 0.3838 (6) | 0.8758 (4) | 0.0325 (11) | |
O3 | 0.2325 (6) | 0.0105 (5) | 0.4633 (4) | 0.0482 (10) | |
H3 | 0.3376 | 0.0060 | 0.4452 | 0.072* | |
O2 | 0.1316 (6) | 0.1865 (5) | 0.5846 (4) | 0.0501 (10) | |
C8 | 0.2643 (7) | 0.1510 (7) | 0.5417 (4) | 0.0339 (11) | |
C6 | 0.5028 (8) | 0.4224 (7) | 0.6713 (5) | 0.0388 (12) | |
H6A | 0.6349 | 0.4996 | 0.6827 | 0.047* | |
H6B | 0.4013 | 0.4854 | 0.6459 | 0.047* | |
C7 | 0.4722 (8) | 0.2676 (7) | 0.5728 (5) | 0.0382 (12) | |
H7A | 0.4960 | 0.3088 | 0.5009 | 0.046* | |
H7B | 0.5707 | 0.2023 | 0.5996 | 0.046* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0356 (3) | 0.0641 (4) | 0.0475 (4) | −0.0056 (3) | 0.0067 (3) | 0.0071 (3) |
Br2 | 0.0557 (4) | 0.0481 (4) | 0.0446 (3) | 0.0027 (3) | 0.0252 (3) | 0.0146 (2) |
Br3 | 0.0458 (4) | 0.0883 (5) | 0.0368 (3) | 0.0174 (3) | 0.0034 (3) | 0.0250 (3) |
N1 | 0.026 (2) | 0.046 (3) | 0.027 (2) | 0.0028 (19) | 0.0075 (17) | 0.0099 (18) |
C3 | 0.025 (2) | 0.030 (2) | 0.031 (2) | 0.0031 (19) | 0.0071 (19) | 0.0047 (19) |
C4 | 0.034 (3) | 0.032 (3) | 0.029 (2) | 0.011 (2) | 0.011 (2) | 0.003 (2) |
C1 | 0.041 (3) | 0.043 (3) | 0.027 (2) | 0.014 (2) | 0.009 (2) | 0.010 (2) |
C2 | 0.035 (3) | 0.031 (3) | 0.035 (3) | 0.006 (2) | 0.013 (2) | 0.005 (2) |
N2 | 0.029 (2) | 0.040 (2) | 0.031 (2) | 0.0007 (18) | 0.0051 (17) | 0.0087 (18) |
O1 | 0.032 (2) | 0.083 (3) | 0.038 (2) | −0.006 (2) | 0.0065 (17) | 0.024 (2) |
C5 | 0.030 (3) | 0.032 (3) | 0.028 (2) | 0.002 (2) | 0.003 (2) | 0.0013 (19) |
O3 | 0.045 (2) | 0.045 (2) | 0.051 (2) | 0.0030 (18) | 0.0205 (19) | −0.0063 (18) |
O2 | 0.036 (2) | 0.059 (3) | 0.047 (2) | 0.0061 (19) | 0.0110 (18) | −0.0091 (19) |
C8 | 0.035 (3) | 0.041 (3) | 0.026 (2) | 0.011 (2) | 0.005 (2) | 0.007 (2) |
C6 | 0.038 (3) | 0.040 (3) | 0.033 (3) | 0.002 (2) | 0.005 (2) | 0.012 (2) |
C7 | 0.037 (3) | 0.044 (3) | 0.034 (3) | 0.005 (2) | 0.014 (2) | 0.010 (2) |
Br1—C3 | 1.873 (5) | N2—H2 | 0.8600 |
Br2—C2 | 1.863 (5) | O1—C5 | 1.224 (6) |
Br3—C1 | 1.863 (5) | O3—C8 | 1.303 (6) |
N1—C1 | 1.348 (6) | O3—H3 | 0.8200 |
N1—C4 | 1.366 (6) | O2—C8 | 1.223 (6) |
N1—H1 | 0.8600 | C8—C7 | 1.493 (7) |
C3—C4 | 1.392 (7) | C6—C7 | 1.523 (8) |
C3—C2 | 1.404 (7) | C6—H6A | 0.9700 |
C4—C5 | 1.456 (7) | C6—H6B | 0.9700 |
C1—C2 | 1.357 (7) | C7—H7A | 0.9700 |
N2—C5 | 1.336 (6) | C7—H7B | 0.9700 |
N2—C6 | 1.444 (6) | ||
C1—N1—C4 | 109.7 (4) | O1—C5—C4 | 120.5 (4) |
C1—N1—H1 | 125.1 | N2—C5—C4 | 118.1 (4) |
C4—N1—H1 | 125.1 | C8—O3—H3 | 109.5 |
C4—C3—C2 | 107.9 (4) | O2—C8—O3 | 122.2 (5) |
C4—C3—Br1 | 128.1 (4) | O2—C8—C7 | 122.4 (5) |
C2—C3—Br1 | 123.9 (4) | O3—C8—C7 | 115.3 (4) |
N1—C4—C3 | 106.3 (4) | N2—C6—C7 | 111.8 (4) |
N1—C4—C5 | 118.2 (4) | N2—C6—H6A | 109.3 |
C3—C4—C5 | 135.4 (4) | C7—C6—H6A | 109.3 |
N1—C1—C2 | 109.4 (4) | N2—C6—H6B | 109.3 |
N1—C1—Br3 | 122.4 (4) | C7—C6—H6B | 109.3 |
C2—C1—Br3 | 128.2 (4) | H6A—C6—H6B | 107.9 |
C1—C2—C3 | 106.6 (4) | C8—C7—C6 | 112.4 (4) |
C1—C2—Br2 | 126.4 (4) | C8—C7—H7A | 109.1 |
C3—C2—Br2 | 127.0 (4) | C6—C7—H7A | 109.1 |
C5—N2—C6 | 122.5 (4) | C8—C7—H7B | 109.1 |
C5—N2—H2 | 118.7 | C6—C7—H7B | 109.1 |
C6—N2—H2 | 118.7 | H7A—C7—H7B | 107.9 |
O1—C5—N2 | 121.4 (5) | ||
C1—N1—C4—C3 | −0.1 (6) | Br1—C3—C2—C1 | −178.3 (4) |
C1—N1—C4—C5 | −177.7 (4) | C4—C3—C2—Br2 | 178.9 (4) |
C2—C3—C4—N1 | 0.5 (5) | Br1—C3—C2—Br2 | 1.3 (7) |
Br1—C3—C4—N1 | 178.0 (4) | C6—N2—C5—O1 | 1.9 (8) |
C2—C3—C4—C5 | 177.5 (5) | C6—N2—C5—C4 | −178.0 (5) |
Br1—C3—C4—C5 | −5.0 (9) | N1—C4—C5—O1 | 6.7 (7) |
C4—N1—C1—C2 | −0.4 (6) | C3—C4—C5—O1 | −170.0 (6) |
C4—N1—C1—Br3 | −178.3 (4) | N1—C4—C5—N2 | −173.4 (4) |
N1—C1—C2—C3 | 0.7 (6) | C3—C4—C5—N2 | 9.9 (9) |
Br3—C1—C2—C3 | 178.4 (4) | C5—N2—C6—C7 | 102.4 (5) |
N1—C1—C2—Br2 | −178.9 (4) | O2—C8—C7—C6 | 5.7 (7) |
Br3—C1—C2—Br2 | −1.2 (8) | O3—C8—C7—C6 | −175.9 (4) |
C4—C3—C2—C1 | −0.7 (6) | N2—C6—C7—C8 | 64.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···Br2i | 0.82 | 2.75 | 3.217 (4) | 118 |
N1—H1···O1ii | 0.86 | 1.93 | 2.777 (5) | 168 |
Symmetry codes: (i) x, y, z−1; (ii) −x+2, −y+1, −z+2. |