Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680200942X/cm6007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680200942X/cm6007Isup2.hkl |
CCDC reference: 189416
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.006 Å
- R factor = 0.055
- wR factor = 0.148
- Data-to-parameter ratio = 17.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.946 0.999 Tmin and Tmax expected: 0.335 0.494 RR = 1.395 Please check that your absorption correction is appropriate. RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.103 PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(21) - C(22) = 1.44 Ang. General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.495 Tmax scaled 0.494 Tmin scaled 0.468
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
3 Alert Level C = Please check
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999).
C14H10Br2·0.5C14H10 | Dx = 1.646 Mg m−3 |
Mr = 427.15 | Melting point = 68–71 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.8445 (5) Å | Cell parameters from 13506 reflections |
b = 5.7702 (3) Å | θ = 1.0–27.1° |
c = 20.741 (9) Å | µ = 4.70 mm−1 |
β = 104.037 (2)° | T = 150 K |
V = 1723.5 (8) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.20 × 0.15 mm |
F(000) = 844 |
Enraf–Nonius KappaCCD area-detector diffractometer | 3718 independent reflections |
Radiation source: Enraf–Nonius FR591 rotating anode | 2614 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.103 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.1°, θmin = 2.8° |
φ and ω scans | h = −19→18 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −6→7 |
Tmin = 0.946, Tmax = 0.999 | l = −23→26 |
11791 measured reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0826P)2] where P = (Fo2 + 2Fc2)/3 |
3718 reflections | (Δ/σ)max = 0.002 |
208 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −0.95 e Å−3 |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
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 | 0.55860 (4) | 0.41738 (10) | 0.08283 (2) | 0.0458 (2) | |
Br2 | 0.39224 (3) | 0.74326 (8) | 0.11248 (2) | 0.03678 (19) | |
C1 | 0.5219 (3) | 0.3848 (8) | 0.1643 (2) | 0.0270 (9) | |
C2 | 0.4530 (3) | 0.5159 (8) | 0.1751 (2) | 0.0268 (9) | |
C3 | 0.5766 (3) | 0.2153 (8) | 0.2110 (2) | 0.0268 (10) | |
C4 | 0.6070 (3) | 0.0098 (8) | 0.1873 (2) | 0.0293 (10) | |
H4 | 0.5929 | −0.0190 | 0.1409 | 0.038* | |
C5 | 0.6576 (3) | −0.1518 (8) | 0.2308 (2) | 0.0303 (10) | |
H5 | 0.6764 | −0.2925 | 0.2141 | 0.039* | |
C6 | 0.6808 (3) | −0.1085 (8) | 0.2987 (2) | 0.0309 (10) | |
H6 | 0.7164 | −0.2179 | 0.3286 | 0.040* | |
C7 | 0.6518 (3) | 0.0947 (8) | 0.3226 (2) | 0.0296 (10) | |
H7 | 0.6670 | 0.1242 | 0.3690 | 0.038* | |
C8 | 0.6005 (3) | 0.2562 (7) | 0.2790 (2) | 0.0247 (9) | |
H8 | 0.5816 | 0.3963 | 0.2959 | 0.032* | |
C9 | 0.4140 (3) | 0.5057 (8) | 0.2344 (2) | 0.0277 (9) | |
C10 | 0.3636 (3) | 0.3103 (8) | 0.2446 (2) | 0.0307 (10) | |
H10 | 0.3551 | 0.1841 | 0.2142 | 0.040* | |
C11 | 0.3260 (3) | 0.3032 (9) | 0.2996 (2) | 0.0365 (11) | |
H11 | 0.2906 | 0.1725 | 0.3065 | 0.047* | |
C12 | 0.3394 (3) | 0.4827 (9) | 0.3440 (2) | 0.0342 (11) | |
H12 | 0.3149 | 0.4740 | 0.3822 | 0.044* | |
C13 | 0.3885 (3) | 0.6765 (9) | 0.3335 (2) | 0.0323 (10) | |
H13 | 0.3965 | 0.8017 | 0.3641 | 0.042* | |
C14 | 0.4259 (3) | 0.6900 (8) | 0.2792 (2) | 0.0297 (10) | |
H14 | 0.4595 | 0.8239 | 0.2723 | 0.039* | |
C21 | 0.0314 (3) | 0.4395 (8) | −0.0025 (2) | 0.0298 (10) | |
C22 | 0.1070 (3) | 0.2943 (8) | −0.0099 (2) | 0.0272 (9) | |
C23 | 0.1989 (3) | 0.3597 (9) | 0.0163 (2) | 0.0327 (10) | |
H23 | 0.2122 | 0.5010 | 0.0402 | 0.042* | |
C24 | 0.2706 (3) | 0.2210 (9) | 0.0078 (3) | 0.0388 (12) | |
H24 | 0.3332 | 0.2675 | 0.0253 | 0.050* | |
C25 | 0.2511 (4) | 0.0119 (9) | −0.0267 (3) | 0.0402 (12) | |
H25 | 0.3004 | −0.0831 | −0.0332 | 0.052* | |
C26 | 0.1613 (4) | −0.0558 (8) | −0.0508 (2) | 0.0391 (12) | |
H26 | 0.1485 | −0.1998 | −0.0734 | 0.051* | |
C27 | 0.0886 (3) | 0.0822 (8) | −0.0430 (2) | 0.0330 (10) | |
H27 | 0.0263 | 0.0330 | −0.0601 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0533 (3) | 0.0566 (4) | 0.0297 (3) | 0.0133 (3) | 0.0145 (2) | 0.0060 (2) |
Br2 | 0.0353 (3) | 0.0369 (3) | 0.0344 (3) | 0.0050 (2) | 0.0013 (2) | 0.0055 (2) |
C1 | 0.032 (2) | 0.026 (3) | 0.022 (2) | −0.0041 (19) | 0.0041 (18) | −0.0001 (18) |
C2 | 0.0252 (19) | 0.024 (2) | 0.029 (2) | 0.0000 (18) | 0.0016 (18) | 0.0000 (19) |
C3 | 0.0236 (19) | 0.028 (3) | 0.030 (2) | −0.0003 (18) | 0.0083 (19) | −0.0012 (19) |
C4 | 0.027 (2) | 0.030 (3) | 0.033 (2) | 0.0004 (19) | 0.0106 (19) | −0.007 (2) |
C5 | 0.031 (2) | 0.023 (2) | 0.040 (3) | −0.0023 (19) | 0.014 (2) | −0.006 (2) |
C6 | 0.027 (2) | 0.026 (3) | 0.040 (3) | −0.0009 (18) | 0.008 (2) | 0.009 (2) |
C7 | 0.032 (2) | 0.028 (3) | 0.030 (2) | −0.0015 (19) | 0.010 (2) | 0.003 (2) |
C8 | 0.027 (2) | 0.023 (2) | 0.025 (2) | 0.0010 (17) | 0.0064 (18) | −0.0025 (17) |
C9 | 0.0243 (19) | 0.030 (3) | 0.027 (2) | 0.0029 (19) | 0.0031 (18) | 0.0011 (19) |
C10 | 0.026 (2) | 0.027 (3) | 0.036 (3) | 0.0010 (18) | 0.002 (2) | −0.002 (2) |
C11 | 0.031 (2) | 0.037 (3) | 0.041 (3) | 0.002 (2) | 0.007 (2) | 0.006 (2) |
C12 | 0.030 (2) | 0.041 (3) | 0.031 (2) | 0.008 (2) | 0.006 (2) | 0.005 (2) |
C13 | 0.033 (2) | 0.034 (3) | 0.027 (2) | 0.005 (2) | 0.002 (2) | −0.003 (2) |
C14 | 0.030 (2) | 0.022 (2) | 0.035 (2) | 0.0006 (19) | 0.003 (2) | −0.003 (2) |
C21 | 0.031 (2) | 0.027 (3) | 0.029 (2) | −0.0033 (18) | 0.003 (2) | 0.003 (2) |
C22 | 0.036 (2) | 0.024 (2) | 0.023 (2) | 0.0034 (19) | 0.0087 (19) | 0.0035 (18) |
C23 | 0.037 (2) | 0.027 (3) | 0.033 (2) | 0.000 (2) | 0.007 (2) | 0.000 (2) |
C24 | 0.031 (2) | 0.044 (3) | 0.041 (3) | 0.006 (2) | 0.008 (2) | 0.010 (2) |
C25 | 0.050 (3) | 0.037 (3) | 0.039 (3) | 0.019 (2) | 0.020 (2) | 0.012 (2) |
C26 | 0.062 (3) | 0.023 (3) | 0.035 (3) | 0.007 (2) | 0.017 (3) | 0.001 (2) |
C27 | 0.042 (2) | 0.028 (3) | 0.030 (2) | −0.007 (2) | 0.011 (2) | −0.002 (2) |
Br1—C1 | 1.907 (4) | C11—C12 | 1.368 (7) |
Br2—C2 | 1.912 (4) | C11—H11 | 0.9500 |
C1—C2 | 1.334 (6) | C12—C13 | 1.381 (7) |
C1—C3 | 1.474 (6) | C12—H12 | 0.9500 |
C2—C9 | 1.481 (6) | C13—C14 | 1.371 (6) |
C3—C8 | 1.388 (6) | C13—H13 | 0.9500 |
C3—C4 | 1.400 (6) | C14—H14 | 0.9500 |
C4—C5 | 1.384 (7) | C21—C21i | 1.188 (9) |
C4—H4 | 0.9500 | C21—C22 | 1.439 (6) |
C5—C6 | 1.390 (7) | C22—C23 | 1.393 (6) |
C5—H5 | 0.9500 | C22—C27 | 1.397 (6) |
C6—C7 | 1.381 (7) | C23—C24 | 1.377 (7) |
C6—H6 | 0.9500 | C23—H23 | 0.9500 |
C7—C8 | 1.390 (6) | C24—C25 | 1.396 (7) |
C7—H7 | 0.9500 | C24—H24 | 0.9500 |
C8—H8 | 0.9500 | C25—C26 | 1.362 (8) |
C9—C14 | 1.396 (6) | C25—H25 | 0.9500 |
C9—C10 | 1.398 (6) | C26—C27 | 1.382 (7) |
C10—C11 | 1.387 (7) | C26—H26 | 0.9500 |
C10—H10 | 0.9500 | C27—H27 | 0.9500 |
C2—C1—C3 | 126.1 (4) | C12—C11—H11 | 119.7 |
C2—C1—Br1 | 119.2 (3) | C10—C11—H11 | 119.7 |
C3—C1—Br1 | 114.7 (3) | C11—C12—C13 | 120.2 (4) |
C1—C2—C9 | 125.9 (4) | C11—C12—H12 | 119.9 |
C1—C2—Br2 | 122.0 (3) | C13—C12—H12 | 119.9 |
C9—C2—Br2 | 112.1 (3) | C14—C13—C12 | 120.6 (5) |
C8—C3—C4 | 118.4 (4) | C14—C13—H13 | 119.7 |
C8—C3—C1 | 121.3 (4) | C12—C13—H13 | 119.7 |
C4—C3—C1 | 120.3 (4) | C13—C14—C9 | 119.5 (4) |
C5—C4—C3 | 120.8 (4) | C13—C14—H14 | 120.2 |
C5—C4—H4 | 119.6 | C9—C14—H14 | 120.2 |
C3—C4—H4 | 119.6 | C21i—C21—C22 | 178.8 (6) |
C4—C5—C6 | 120.1 (4) | C23—C22—C27 | 119.0 (4) |
C4—C5—H5 | 120.0 | C23—C22—C21 | 121.1 (4) |
C6—C5—H5 | 120.0 | C27—C22—C21 | 119.9 (4) |
C7—C6—C5 | 119.6 (4) | C24—C23—C22 | 120.5 (5) |
C7—C6—H6 | 120.2 | C24—C23—H23 | 119.8 |
C5—C6—H6 | 120.2 | C22—C23—H23 | 119.8 |
C6—C7—C8 | 120.4 (4) | C23—C24—C25 | 119.8 (5) |
C6—C7—H7 | 119.8 | C23—C24—H24 | 120.1 |
C8—C7—H7 | 119.8 | C25—C24—H24 | 120.1 |
C3—C8—C7 | 120.7 (4) | C26—C25—C24 | 120.0 (4) |
C3—C8—H8 | 119.6 | C26—C25—H25 | 120.0 |
C7—C8—H8 | 119.6 | C24—C25—H25 | 120.0 |
C14—C9—C10 | 119.9 (4) | C25—C26—C27 | 120.9 (5) |
C14—C9—C2 | 120.8 (4) | C25—C26—H26 | 119.5 |
C10—C9—C2 | 119.3 (4) | C27—C26—H26 | 119.5 |
C11—C10—C9 | 119.0 (4) | C26—C27—C22 | 119.8 (5) |
C11—C10—H10 | 120.5 | C26—C27—H27 | 120.1 |
C9—C10—H10 | 120.5 | C22—C27—H27 | 120.1 |
C12—C11—C10 | 120.6 (5) | ||
C4—C3—C1—C2 | 144.5 (5) | C10—C9—C2—Br2 | 111.1 (4) |
C3—C1—C2—C9 | −4.2 (7) | C14—C9—C2—C1 | 112.5 (5) |
C1—C2—C9—C10 | −68.6 (6) | Br1—C1—C2—Br2 | −2.0 (5) |
C4—C3—C1—Br1 | −37.2 (5) |
Symmetry code: (i) −x, −y+1, −z. |
Compound | C4-C3-C1-C2 | C14-C9-C2-C1 | C3-C1-C2-C9 |
1,2-dibromo_(obs) | 144.5 (4) | 112.9 (5) | -4.4 (7) |
1,2-dibromo_(calc) | 120 | 114 | 0.2 |
1,2-dichloro_(obs) | 133.7 | 111.3 | -8.7 |
1,2-dichloro_(calc) | 122 | 115 | 0.3 |
4-ClPh-1,2-dichloro_(obs) | 129.3 | 128.0 | 7.1 |
4-ClPh-1,2-dichloro_(calc) | 118 | 115 | 0.1 |
cis-stilbene_(calc) | 121 | 117 | 0.1 |