Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025614/bt6714sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025614/bt6714Isup2.hkl |
CCDC reference: 283759
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.057
- Data-to-parameter ratio = 23.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H6 .. BR .. 3.13 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. BR .. 3.16 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
C20H16Br2 | Z = 1 |
Mr = 416.15 | F(000) = 206 |
Triclinic, P1 | Dx = 1.715 Mg m−3 |
a = 4.4286 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.4756 (6) Å | Cell parameters from 4465 reflections |
c = 12.4664 (12) Å | θ = 2.7–30.4° |
α = 96.032 (4)° | µ = 5.02 mm−1 |
β = 98.347 (4)° | T = 133 K |
γ = 96.155 (4)° | Rectangular prism, colourless |
V = 402.93 (6) Å3 | 0.25 × 0.10 × 0.07 mm |
Bruker SMART 1000 CCD diffractometer | 2348 independent reflections |
Radiation source: fine-focus sealed tube | 2056 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.192 pixels mm-1 | θmax = 30.0°, θmin = 1.7° |
ω and φ scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −10→10 |
Tmin = 0.488, Tmax = 0.704 | l = −17→17 |
8315 measured reflections |
Refinement on F2 | Primary atom site location: Patterson |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: riding |
wR(F2) = 0.057 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.032P)2] where P = (Fo2 + 2Fc2)/3 |
2348 reflections | (Δ/σ)max < 0.001 |
100 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 3.4213 (0.0021) x + 4.6406 (0.0041) y + 4.6478 (0.0082) z = 2.9298 (0.0045) * -0.0067 (0.0012) C4 * 0.0024 (0.0012) C5 * 0.0034 (0.0013) C6 * -0.0049 (0.0013) C7 * 0.0004 (0.0014) C8 * 0.0054 (0.0013) C9 Rms deviation of fitted atoms = 0.0044 4.2200 (0.0015) x - 0.0032 (0.0081) y + 1.6154 (0.0130) z = 2.9161 (0.0067) Angle to previous plane (with approximate e.s.d.) = 54.13 (0.06) * -0.0013 (0.0011) C1 * 0.0013 (0.0011) C2 * -0.0013 (0.0010) C3 * 0.0013 (0.0011) C1_$3 * -0.0013 (0.0011) C2_$3 * 0.0013 (0.0010) C3_$3 Rms deviation of fitted atoms = 0.0013 |
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 | ||
Br | 0.25108 (4) | 0.34454 (2) | 0.100201 (14) | 0.02420 (7) | |
C1 | 0.5066 (4) | 0.3147 (2) | 0.48155 (14) | 0.0205 (3) | |
H1 | 0.5108 | 0.1876 | 0.4682 | 0.025* | |
C2 | 0.5393 (4) | 0.4203 (2) | 0.39786 (13) | 0.0210 (4) | |
H2 | 0.5667 | 0.3648 | 0.3284 | 0.025* | |
C3 | 0.5324 (4) | 0.6086 (2) | 0.41475 (13) | 0.0185 (3) | |
C4 | 0.5764 (4) | 0.7268 (2) | 0.32756 (13) | 0.0179 (3) | |
C5 | 0.3932 (4) | 0.6977 (2) | 0.22374 (13) | 0.0173 (3) | |
C6 | 0.4493 (4) | 0.8159 (2) | 0.14722 (14) | 0.0208 (3) | |
H6 | 0.3256 | 0.7964 | 0.0771 | 0.025* | |
C7 | 0.6806 (4) | 0.9607 (2) | 0.17112 (15) | 0.0240 (4) | |
H7 | 0.7165 | 1.0387 | 0.1176 | 0.029* | |
C8 | 0.8594 (5) | 0.9909 (2) | 0.27374 (16) | 0.0252 (4) | |
H8 | 1.0179 | 1.0903 | 0.2912 | 0.030* | |
C9 | 0.8057 (4) | 0.8749 (2) | 0.35103 (14) | 0.0225 (4) | |
H9 | 0.9278 | 0.8971 | 0.4214 | 0.027* | |
C10 | 0.1314 (4) | 0.5490 (2) | 0.19254 (14) | 0.0196 (3) | |
H10A | −0.0464 | 0.5961 | 0.1521 | 0.024* | |
H10B | 0.0685 | 0.5057 | 0.2593 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br | 0.02757 (12) | 0.02080 (10) | 0.02267 (10) | 0.00043 (7) | 0.00274 (7) | −0.00022 (6) |
C1 | 0.0259 (10) | 0.0172 (8) | 0.0187 (8) | 0.0053 (7) | 0.0032 (6) | 0.0016 (6) |
C2 | 0.0265 (10) | 0.0219 (8) | 0.0150 (8) | 0.0065 (7) | 0.0036 (6) | 0.0006 (6) |
C3 | 0.0190 (9) | 0.0206 (8) | 0.0163 (7) | 0.0040 (6) | 0.0020 (6) | 0.0037 (6) |
C4 | 0.0201 (9) | 0.0175 (8) | 0.0176 (7) | 0.0057 (6) | 0.0044 (6) | 0.0030 (6) |
C5 | 0.0178 (9) | 0.0176 (8) | 0.0176 (8) | 0.0054 (6) | 0.0046 (6) | 0.0022 (6) |
C6 | 0.0230 (10) | 0.0221 (8) | 0.0183 (8) | 0.0054 (7) | 0.0026 (6) | 0.0052 (6) |
C7 | 0.0280 (11) | 0.0197 (8) | 0.0276 (9) | 0.0051 (7) | 0.0092 (7) | 0.0086 (7) |
C8 | 0.0258 (11) | 0.0187 (8) | 0.0298 (9) | −0.0013 (7) | 0.0040 (7) | 0.0013 (7) |
C9 | 0.0246 (10) | 0.0214 (9) | 0.0200 (8) | 0.0027 (7) | 0.0010 (7) | −0.0004 (7) |
C10 | 0.0191 (9) | 0.0213 (8) | 0.0186 (8) | 0.0028 (6) | 0.0030 (6) | 0.0025 (6) |
Br—C10 | 1.9806 (17) | C7—C8 | 1.386 (3) |
C1—C2 | 1.388 (2) | C8—C9 | 1.391 (3) |
C1—C3i | 1.400 (2) | C1—H1 | 0.9500 |
C2—C3 | 1.405 (2) | C2—H2 | 0.9500 |
C3—C4 | 1.492 (2) | C6—H6 | 0.9500 |
C4—C9 | 1.395 (2) | C7—H7 | 0.9500 |
C4—C5 | 1.407 (2) | C8—H8 | 0.9500 |
C5—C6 | 1.397 (2) | C9—H9 | 0.9500 |
C5—C10 | 1.494 (2) | C10—H10A | 0.9900 |
C6—C7 | 1.384 (3) | C10—H10B | 0.9900 |
C2—C1—C3i | 121.42 (16) | C3i—C1—H1 | 119.3 |
C1—C2—C3 | 120.71 (15) | C1—C2—H2 | 119.6 |
C1i—C3—C2 | 117.87 (15) | C3—C2—H2 | 119.6 |
C1i—C3—C4 | 120.05 (15) | C7—C6—H6 | 119.2 |
C2—C3—C4 | 122.04 (15) | C5—C6—H6 | 119.2 |
C9—C4—C5 | 118.65 (15) | C6—C7—H7 | 120.3 |
C9—C4—C3 | 118.39 (15) | C8—C7—H7 | 120.3 |
C5—C4—C3 | 122.95 (16) | C7—C8—H8 | 120.2 |
C6—C5—C4 | 119.13 (16) | C9—C8—H8 | 120.2 |
C6—C5—C10 | 118.04 (15) | C8—C9—H9 | 119.2 |
C4—C5—C10 | 122.79 (15) | C4—C9—H9 | 119.2 |
C7—C6—C5 | 121.58 (16) | C5—C10—H10A | 109.5 |
C6—C7—C8 | 119.43 (16) | Br—C10—H10A | 109.5 |
C7—C8—C9 | 119.70 (17) | C5—C10—H10B | 109.5 |
C8—C9—C4 | 121.50 (17) | Br—C10—H10B | 109.5 |
C5—C10—Br | 110.67 (12) | H10A—C10—H10B | 108.1 |
C2—C1—H1 | 119.3 | ||
C3i—C1—C2—C3 | −0.4 (3) | C3—C4—C5—C10 | 2.0 (3) |
C1—C2—C3—C1i | 0.4 (3) | C4—C5—C6—C7 | 0.0 (3) |
C1—C2—C3—C4 | 178.10 (17) | C10—C5—C6—C7 | 177.77 (16) |
C1i—C3—C4—C9 | 52.3 (2) | C5—C6—C7—C8 | −0.7 (3) |
C2—C3—C4—C9 | −125.40 (19) | C6—C7—C8—C9 | 0.4 (3) |
C1i—C3—C4—C5 | −126.36 (19) | C7—C8—C9—C4 | 0.6 (3) |
C2—C3—C4—C5 | 55.9 (3) | C5—C4—C9—C8 | −1.2 (3) |
C9—C4—C5—C6 | 0.9 (2) | C3—C4—C9—C8 | −179.95 (16) |
C3—C4—C5—C6 | 179.58 (16) | C6—C5—C10—Br | 79.98 (17) |
C9—C4—C5—C10 | −176.70 (16) | C4—C5—C10—Br | −102.37 (16) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···Brii | 0.95 | 3.13 | 4.0272 (18) | 158 |
C7—H7···Briii | 0.95 | 3.16 | 3.8764 (18) | 134 |
Symmetry codes: (ii) −x, −y+1, −z; (iii) x+1, y+1, z. |
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