Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031734/hk2104sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031734/hk2104Isup2.hkl |
CCDC reference: 621366
Data collection: SMART (Bruker, 1995); cell refinement: SAINT; data reduction: SAINT and XPREP (Bruker, 1995); program(s) used to solve structure: SIR97 (Altomare et al. 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN for Windows (Molecular Structure Corporation, 1998), Xtal3.6 (Hall et al., 1999) ORTEPII (Johnson, 1976); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H10Br4N2 | Dx = 2.323 Mg m−3 |
Mr = 537.89 | Melting point: 498.33K K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 1012 reflections |
a = 8.040 (3) Å | θ = 3.0–28.3° |
b = 12.475 (4) Å | µ = 10.46 mm−1 |
c = 15.331 (5) Å | T = 150 K |
V = 1537.7 (9) Å3 | Plate, colorless |
Z = 4 | 0.48 × 0.30 × 0.06 mm |
F(000) = 1016 |
Bruker SMART 1000 CCD diffractometer | 3662 independent reflections |
Radiation source: sealed tube | 3419 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: gaussian [(Coppens et al., 1965) using XPREP (Bruker, 1995)] | h = −10→10 |
Tmin = 0.042, Tmax = 0.519 | k = −16→16 |
13979 measured reflections | l = −19→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.053 | w = 1/[σ2(Fo2) + (0.02P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.13 | (Δ/σ)max = 0.002 |
3662 reflections | Δρmax = 0.60 e Å−3 |
191 parameters | Δρmin = −0.66 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1686 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.004 (10) |
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 | 0.48729 (5) | −0.01522 (3) | 0.26532 (2) | 0.02456 (9) | |
Br2 | 0.30256 (5) | −0.19191 (3) | 0.59144 (2) | 0.02592 (9) | |
Br3 | 0.07020 (5) | 0.45333 (3) | 0.56818 (2) | 0.02194 (9) | |
Br4 | −0.26941 (4) | 0.41528 (4) | 0.24542 (2) | 0.02277 (9) | |
N1 | 0.3313 (4) | 0.3179 (3) | 0.47455 (17) | 0.0175 (6) | |
N2 | 0.4448 (4) | 0.1997 (3) | 0.36359 (18) | 0.0177 (6) | |
C1 | 0.3971 (4) | 0.1088 (3) | 0.4143 (2) | 0.0186 (7) | |
C2 | 0.4128 (5) | 0.0048 (3) | 0.3821 (2) | 0.0197 (8) | |
C3 | 0.3808 (5) | −0.0860 (3) | 0.4319 (2) | 0.0211 (8) | |
H3 | 0.3915 | −0.1559 | 0.4078 | 0.025* | |
C4 | 0.3326 (5) | −0.0711 (3) | 0.5182 (2) | 0.0216 (8) | |
C5 | 0.3095 (4) | 0.0304 (3) | 0.5521 (2) | 0.0202 (8) | |
H5 | 0.2727 | 0.0386 | 0.6106 | 0.024* | |
C6 | 0.3400 (4) | 0.1211 (3) | 0.50080 (19) | 0.0184 (7) | |
C7 | 0.3149 (5) | 0.2320 (3) | 0.5397 (2) | 0.0192 (7) | |
H7A | 0.2030 | 0.2359 | 0.5664 | 0.023* | |
H7B | 0.3979 | 0.2435 | 0.5865 | 0.023* | |
C8 | 0.1862 (4) | 0.3339 (3) | 0.4224 (2) | 0.0178 (7) | |
C9 | 0.0536 (5) | 0.3930 (3) | 0.45464 (19) | 0.0174 (7) | |
C10 | −0.0862 (4) | 0.4155 (3) | 0.4050 (2) | 0.0182 (7) | |
H10 | −0.1772 | 0.4544 | 0.4286 | 0.022* | |
C11 | −0.0880 (4) | 0.3790 (3) | 0.31942 (19) | 0.0190 (8) | |
C12 | 0.0398 (5) | 0.3196 (3) | 0.28527 (19) | 0.0182 (8) | |
H12 | 0.0331 | 0.2941 | 0.2270 | 0.022* | |
C13 | 0.1794 (5) | 0.2964 (3) | 0.3356 (2) | 0.0169 (7) | |
C14 | 0.3210 (4) | 0.2325 (3) | 0.2975 (2) | 0.0190 (8) | |
H14A | 0.2756 | 0.1676 | 0.2689 | 0.023* | |
H14B | 0.3771 | 0.2759 | 0.2522 | 0.023* | |
C15 | 0.4756 (5) | 0.2929 (3) | 0.4195 (2) | 0.0204 (8) | |
H15A | 0.5020 | 0.3557 | 0.3825 | 0.024* | |
H15B | 0.5732 | 0.2784 | 0.4571 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02964 (19) | 0.0267 (2) | 0.01731 (15) | 0.00924 (18) | 0.00462 (15) | −0.00175 (15) |
Br2 | 0.0328 (2) | 0.0220 (2) | 0.02292 (16) | 0.00012 (19) | −0.00032 (15) | 0.00505 (15) |
Br3 | 0.02755 (18) | 0.02223 (19) | 0.01603 (13) | −0.00005 (17) | 0.00181 (13) | −0.00601 (14) |
Br4 | 0.02162 (16) | 0.0277 (2) | 0.01895 (16) | 0.00446 (17) | −0.00086 (13) | 0.00370 (14) |
N1 | 0.0176 (15) | 0.0167 (16) | 0.0181 (13) | −0.0017 (14) | 0.0002 (11) | −0.0015 (11) |
N2 | 0.0166 (14) | 0.0207 (18) | 0.0157 (12) | −0.0004 (14) | 0.0016 (11) | −0.0005 (11) |
C1 | 0.0156 (16) | 0.023 (2) | 0.0171 (14) | 0.0006 (16) | −0.0011 (12) | 0.0016 (14) |
C2 | 0.0199 (18) | 0.025 (2) | 0.0143 (14) | 0.0048 (16) | −0.0004 (13) | −0.0007 (14) |
C3 | 0.0241 (18) | 0.020 (2) | 0.0195 (15) | 0.0036 (18) | −0.0006 (14) | −0.0009 (14) |
C4 | 0.0227 (19) | 0.023 (2) | 0.0193 (16) | 0.0036 (18) | −0.0017 (14) | 0.0046 (14) |
C5 | 0.0199 (17) | 0.027 (2) | 0.0136 (15) | 0.0035 (17) | −0.0015 (12) | 0.0009 (13) |
C6 | 0.0147 (17) | 0.021 (2) | 0.0191 (15) | 0.0008 (17) | −0.0026 (12) | −0.0029 (14) |
C7 | 0.0233 (18) | 0.019 (2) | 0.0151 (14) | 0.0014 (17) | −0.0015 (13) | −0.0021 (14) |
C8 | 0.0203 (18) | 0.0154 (19) | 0.0177 (15) | −0.0039 (16) | 0.0018 (13) | 0.0010 (13) |
C9 | 0.0225 (17) | 0.017 (2) | 0.0131 (13) | −0.0036 (17) | 0.0023 (12) | −0.0013 (13) |
C10 | 0.0188 (17) | 0.018 (2) | 0.0177 (14) | 0.0003 (16) | 0.0035 (12) | −0.0011 (13) |
C11 | 0.0213 (19) | 0.018 (2) | 0.0179 (15) | −0.0029 (17) | −0.0029 (13) | 0.0032 (13) |
C12 | 0.0246 (18) | 0.019 (2) | 0.0106 (14) | 0.0000 (17) | 0.0009 (12) | 0.0014 (12) |
C13 | 0.0210 (17) | 0.0124 (18) | 0.0173 (14) | −0.0031 (16) | 0.0036 (12) | 0.0009 (13) |
C14 | 0.0196 (18) | 0.024 (2) | 0.0139 (13) | 0.0001 (17) | 0.0010 (13) | −0.0001 (14) |
C15 | 0.0191 (19) | 0.020 (2) | 0.0216 (15) | −0.0046 (17) | 0.0002 (13) | −0.0002 (15) |
Br1—C2 | 1.905 (3) | C5—H5 | 0.9500 |
Br2—C4 | 1.896 (4) | C6—C7 | 1.521 (5) |
Br3—C9 | 1.901 (3) | C7—H7A | 0.9900 |
Br4—C11 | 1.903 (3) | C7—H7B | 0.9900 |
N1—C8 | 1.428 (4) | C8—C9 | 1.387 (5) |
N1—C15 | 1.469 (5) | C8—C13 | 1.411 (5) |
N1—C7 | 1.470 (5) | C9—C10 | 1.386 (5) |
N2—C1 | 1.429 (5) | C10—C11 | 1.390 (4) |
N2—C15 | 1.465 (5) | C10—H10 | 0.9500 |
N2—C14 | 1.478 (5) | C11—C12 | 1.371 (5) |
C1—C2 | 1.394 (5) | C12—C13 | 1.393 (5) |
C1—C6 | 1.411 (4) | C12—H12 | 0.9500 |
C2—C3 | 1.390 (5) | C13—C14 | 1.509 (5) |
C3—C4 | 1.391 (5) | C14—H14A | 0.9900 |
C3—H3 | 0.9500 | C14—H14B | 0.9900 |
C4—C5 | 1.381 (5) | C15—H15A | 0.9900 |
C5—C6 | 1.400 (5) | C15—H15B | 0.9900 |
C8—N1—C15 | 110.7 (3) | C9—C8—C13 | 118.8 (3) |
C8—N1—C7 | 114.2 (3) | C9—C8—N1 | 120.2 (3) |
C15—N1—C7 | 107.9 (3) | C13—C8—N1 | 120.8 (3) |
C1—N2—C15 | 110.9 (3) | C10—C9—C8 | 122.4 (3) |
C1—N2—C14 | 114.3 (3) | C10—C9—Br3 | 118.6 (3) |
C15—N2—C14 | 107.2 (3) | C8—C9—Br3 | 118.9 (3) |
C2—C1—C6 | 117.6 (3) | C9—C10—C11 | 117.4 (3) |
C2—C1—N2 | 121.5 (3) | C9—C10—H10 | 121.3 |
C6—C1—N2 | 120.8 (4) | C11—C10—H10 | 121.3 |
C3—C2—C1 | 123.2 (3) | C12—C11—C10 | 122.0 (3) |
C3—C2—Br1 | 117.9 (3) | C12—C11—Br4 | 118.4 (2) |
C1—C2—Br1 | 118.9 (3) | C10—C11—Br4 | 119.5 (3) |
C2—C3—C4 | 117.6 (4) | C11—C12—C13 | 120.3 (3) |
C2—C3—H3 | 121.2 | C11—C12—H12 | 119.9 |
C4—C3—H3 | 121.2 | C13—C12—H12 | 119.9 |
C5—C4—C3 | 121.3 (4) | C12—C13—C8 | 119.0 (3) |
C5—C4—Br2 | 119.2 (2) | C12—C13—C14 | 120.2 (3) |
C3—C4—Br2 | 119.5 (3) | C8—C13—C14 | 120.8 (3) |
C4—C5—C6 | 120.4 (3) | N2—C14—C13 | 112.8 (3) |
C4—C5—H5 | 119.8 | N2—C14—H14A | 109.0 |
C6—C5—H5 | 119.8 | C13—C14—H14A | 109.0 |
C5—C6—C1 | 119.8 (4) | N2—C14—H14B | 109.0 |
C5—C6—C7 | 119.5 (3) | C13—C14—H14B | 109.0 |
C1—C6—C7 | 120.7 (3) | H14A—C14—H14B | 107.8 |
N1—C7—C6 | 112.6 (3) | N2—C15—N1 | 111.8 (3) |
N1—C7—H7A | 109.1 | N2—C15—H15A | 109.3 |
C6—C7—H7A | 109.1 | N1—C15—H15A | 109.3 |
N1—C7—H7B | 109.1 | N2—C15—H15B | 109.3 |
C6—C7—H7B | 109.1 | N1—C15—H15B | 109.3 |
H7A—C7—H7B | 107.8 | H15A—C15—H15B | 107.9 |
C15—N2—C1—C2 | −159.0 (3) | C15—N1—C8—C13 | 18.2 (5) |
C14—N2—C1—C2 | 79.6 (4) | C7—N1—C8—C13 | −103.7 (4) |
C15—N2—C1—C6 | 17.7 (4) | C13—C8—C9—C10 | 0.8 (6) |
C14—N2—C1—C6 | −103.6 (4) | N1—C8—C9—C10 | 176.6 (3) |
C6—C1—C2—C3 | −2.4 (6) | C13—C8—C9—Br3 | −175.0 (3) |
N2—C1—C2—C3 | 174.5 (3) | N1—C8—C9—Br3 | 0.8 (5) |
C6—C1—C2—Br1 | 179.4 (3) | C8—C9—C10—C11 | −1.8 (6) |
N2—C1—C2—Br1 | −3.8 (5) | Br3—C9—C10—C11 | 174.0 (3) |
C1—C2—C3—C4 | −0.7 (6) | C9—C10—C11—C12 | 2.3 (6) |
Br1—C2—C3—C4 | 177.6 (3) | C9—C10—C11—Br4 | −175.8 (3) |
C2—C3—C4—C5 | 3.0 (6) | C10—C11—C12—C13 | −1.8 (6) |
C2—C3—C4—Br2 | −175.6 (3) | Br4—C11—C12—C13 | 176.3 (3) |
C3—C4—C5—C6 | −2.2 (6) | C11—C12—C13—C8 | 0.8 (6) |
Br2—C4—C5—C6 | 176.4 (3) | C11—C12—C13—C14 | −179.1 (3) |
C4—C5—C6—C1 | −1.0 (6) | C9—C8—C13—C12 | −0.2 (5) |
C4—C5—C6—C7 | −179.6 (3) | N1—C8—C13—C12 | −176.0 (3) |
C2—C1—C6—C5 | 3.2 (5) | C9—C8—C13—C14 | 179.6 (3) |
N2—C1—C6—C5 | −173.7 (3) | N1—C8—C13—C14 | 3.8 (5) |
C2—C1—C6—C7 | −178.2 (3) | C1—N2—C14—C13 | 79.4 (4) |
N2—C1—C6—C7 | 4.9 (5) | C15—N2—C14—C13 | −43.9 (4) |
C8—N1—C7—C6 | 80.4 (4) | C12—C13—C14—N2 | −170.2 (3) |
C15—N1—C7—C6 | −43.1 (4) | C8—C13—C14—N2 | 10.0 (5) |
C5—C6—C7—N1 | −172.6 (3) | C1—N2—C15—N1 | −55.6 (4) |
C1—C6—C7—N1 | 8.8 (5) | C14—N2—C15—N1 | 69.8 (4) |
C15—N1—C8—C9 | −157.5 (4) | C8—N1—C15—N2 | −56.1 (4) |
C7—N1—C8—C9 | 80.5 (4) | C7—N1—C15—N2 | 69.5 (3) |