Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617015504/hb4171sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2414314617015504/hb4171Isup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617015504/hb4171Isup3.cml |
CCDC reference: 1581763
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.009 Å
- R factor = 0.061
- wR factor = 0.193
- Data-to-parameter ratio = 22.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.24 Report PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00929 Ang. PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 10.553 Check PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 2.029 Check PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) . 2 Check PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers .... 1 Check PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S . 19.95 Check PLAT971_ALERT_2_C Check Calcd Residual Density 0.09A From Br1 1.54 eA-3 PLAT977_ALERT_2_C Check the Negative Difference Density on H3 -0.56 eA-3 PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 11.44 Why ? PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 6 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 10 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 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: X-AREA (Stoe & Cie, 2006); cell refinement: X-AREA (Stoe & Cie, 2006); data reduction: X-RED32 (Stoe & Cie, 2006); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: SHELXL2017 (Sheldrick, 2015b); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015b).
C12H14Br2 | Dx = 1.772 Mg m−3 |
Mr = 318.05 | Melting point: 431 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
a = 16.8714 (12) Å | Cell parameters from 9463 reflections |
b = 7.7191 (4) Å | θ = 2.4–28.4° |
c = 9.1556 (5) Å | µ = 6.76 mm−1 |
V = 1192.35 (12) Å3 | T = 120 K |
Z = 4 | Block, colourless |
F(000) = 624 | 0.27 × 0.23 × 0.22 mm |
Stoe IPDS 2T diffractometer | 1465 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1204 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.031 |
Detector resolution: 6.67 pixels mm-1 | θmax = 28.2°, θmin = 2.4° |
rotation method scans | h = −22→22 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2006b) | k = −10→10 |
Tmin = 0.190, Tmax = 0.356 | l = −11→12 |
7295 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.193 | w = 1/[σ2(Fo2) + (0.0757P)2 + 11.4374P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max < 0.001 |
1465 reflections | Δρmax = 1.54 e Å−3 |
64 parameters | Δρmin = −0.69 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Hydrogen atoms attached to carbons were placed at calculated positions with C—H = 0.95 Å (sp2) or 0.99 Å (sp3 C-atom). All H atoms were refined in the riding-model approximation with isotropic displacement parameters (set at 1.2–1.5 times of the Ueq of the parent atom). |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.15412 (3) | 0.49337 (7) | 0.37567 (6) | 0.0204 (3) | |
C1 | 0.0288 (3) | 0.3816 (8) | 0.1832 (7) | 0.0243 (12) | |
H1A | 0.010594 | 0.295662 | 0.110314 | 0.029* | |
H1B | 0.028447 | 0.497259 | 0.136454 | 0.029* | |
C2 | 0.1119 (3) | 0.3376 (8) | 0.2315 (7) | 0.0223 (12) | |
C3 | 0.1575 (3) | 0.2044 (9) | 0.1877 (8) | 0.0265 (13) | |
H3 | 0.208538 | 0.193789 | 0.230594 | 0.032* | |
C4 | 0.1342 (4) | 0.0716 (9) | 0.0768 (8) | 0.0300 (14) | |
H4A | 0.179279 | 0.051056 | 0.009796 | 0.036* | |
H4B | 0.089357 | 0.116479 | 0.018263 | 0.036* | |
C5 | 0.1100 (5) | −0.1000 (9) | 0.1478 (8) | 0.0339 (16) | |
H5A | 0.109077 | −0.191212 | 0.071789 | 0.041* | |
H5B | 0.150743 | −0.132693 | 0.220615 | 0.041* | |
C6 | 0.0324 (4) | −0.0948 (8) | 0.2201 (8) | 0.0305 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0147 (4) | 0.0213 (4) | 0.0251 (4) | −0.00532 (19) | −0.0026 (2) | 0.00172 (19) |
C1 | 0.017 (2) | 0.026 (3) | 0.031 (3) | 0.001 (2) | −0.002 (3) | 0.001 (3) |
C2 | 0.020 (3) | 0.025 (3) | 0.022 (3) | −0.002 (2) | −0.001 (2) | 0.005 (2) |
C3 | 0.018 (3) | 0.031 (3) | 0.031 (3) | 0.002 (2) | 0.001 (2) | 0.005 (3) |
C4 | 0.025 (3) | 0.039 (4) | 0.025 (3) | 0.005 (3) | 0.002 (3) | −0.001 (3) |
C5 | 0.033 (4) | 0.027 (3) | 0.042 (4) | 0.009 (3) | 0.004 (3) | −0.001 (3) |
C6 | 0.038 (3) | 0.025 (3) | 0.029 (3) | −0.001 (3) | −0.002 (3) | 0.000 (3) |
Br1—C2 | 1.922 (6) | C4—C5 | 1.531 (11) |
C1—C2 | 1.509 (8) | C4—H4A | 0.9900 |
C1—C1i | 1.562 (12) | C4—H4B | 0.9900 |
C1—H1A | 0.9900 | C5—C6 | 1.469 (10) |
C1—H1B | 0.9900 | C5—H5A | 0.9900 |
C2—C3 | 1.346 (9) | C5—H5B | 0.9900 |
C3—C4 | 1.495 (10) | C6—C6i | 1.222 (14) |
C3—H3 | 0.9500 | ||
C2—C1—C1i | 110.4 (6) | C3—C4—H4A | 109.2 |
C2—C1—H1A | 109.6 | C5—C4—H4A | 109.2 |
C1i—C1—H1A | 109.6 | C3—C4—H4B | 109.2 |
C2—C1—H1B | 109.6 | C5—C4—H4B | 109.2 |
C1i—C1—H1B | 109.6 | H4A—C4—H4B | 107.9 |
H1A—C1—H1B | 108.1 | C6—C5—C4 | 113.9 (6) |
C3—C2—C1 | 128.0 (6) | C6—C5—H5A | 108.8 |
C3—C2—Br1 | 118.1 (5) | C4—C5—H5A | 108.8 |
C1—C2—Br1 | 113.9 (4) | C6—C5—H5B | 108.8 |
C2—C3—C4 | 125.2 (6) | C4—C5—H5B | 108.8 |
C2—C3—H3 | 117.4 | H5A—C5—H5B | 107.7 |
C4—C3—H3 | 117.4 | C6i—C6—C5 | 178.4 (4) |
C3—C4—C5 | 112.0 (6) | ||
C1i—C1—C2—C3 | 120.5 (6) | Br1—C2—C3—C4 | −179.9 (5) |
C1i—C1—C2—Br1 | −58.5 (4) | C2—C3—C4—C5 | −102.7 (8) |
C1—C2—C3—C4 | 1.2 (11) | C3—C4—C5—C6 | 73.4 (8) |
Symmetry code: (i) −x, y, −z+1/2. |