Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100011496/bm0033sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100011496/bm00337sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100011496/bm00338sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768100011496/bm00339sup4.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768100011496/bm0033sup5.pdf |
CCDC references: 156667; 156668; 156669
For all compounds, data collection: Bruker SMART (Bruker Systems Inc., 1999a); cell refinement: Bruker SMART (Bruker Systems Inc., 1999a); data reduction: Bruker SAINT (Bruker Systems Inc., 1999b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C10H4F4O2 | F(000) = 348 |
Mr = 232.13 | Dx = 1.633 Mg m−3 |
Triclinic, P1 | Melting point = 132–133 K |
a = 8.9002 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2388 (18) Å | Cell parameters from 999 reflections |
c = 9.6721 (19) Å | θ = 0.2–30.6° |
α = 93.73 (3)° | µ = 0.17 mm−1 |
β = 98.73 (3)° | T = 150 K |
γ = 114.46 (3)° | Block, colourless |
V = 708.3 (2) Å3 | 0.7 × 0.3 × 0.2 mm |
Z = 3 |
Bruker SMART CCD diffractometer | 3722 independent reflections |
Radiation source: fine-focus sealed tube | 3376 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
Detector resolution: not relevant pixels mm-1 | θmax = 29.9°, θmin = 2.2° |
ω scans | h = −12→12 |
Absorption correction: empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997) | k = −12→12 |
Tmin = 0.289, Tmax = 0.382 | l = −13→13 |
8674 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | All H-atom parameters refined |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0484P)2 + 0.2454P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3722 reflections | Δρmax = 0.46 e Å−3 |
242 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.080 (5) |
C10H4F4O2 | γ = 114.46 (3)° |
Mr = 232.13 | V = 708.3 (2) Å3 |
Triclinic, P1 | Z = 3 |
a = 8.9002 (18) Å | Mo Kα radiation |
b = 9.2388 (18) Å | µ = 0.17 mm−1 |
c = 9.6721 (19) Å | T = 150 K |
α = 93.73 (3)° | 0.7 × 0.3 × 0.2 mm |
β = 98.73 (3)° |
Bruker SMART CCD diffractometer | 3722 independent reflections |
Absorption correction: empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997) | 3376 reflections with I > 2σ(I) |
Tmin = 0.289, Tmax = 0.382 | Rint = 0.029 |
8674 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.093 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.46 e Å−3 |
3722 reflections | Δρmin = −0.24 e Å−3 |
242 parameters |
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 | ||
F1 | 0.13140 (9) | 0.32812 (9) | 0.85824 (8) | 0.02992 (17) | |
F2 | 0.10278 (9) | 0.82232 (8) | 0.99013 (8) | 0.02855 (17) | |
F21 | −0.45397 (9) | −0.00542 (9) | 0.78559 (7) | 0.02882 (17) | |
F11 | 0.54677 (9) | 0.58373 (9) | 1.23827 (7) | 0.03106 (18) | |
O21 | −0.70633 (11) | −0.25896 (9) | 0.57778 (9) | 0.02384 (17) | |
F22 | −0.18494 (8) | 0.15228 (9) | 0.66778 (7) | 0.02902 (17) | |
O11 | 0.24851 (10) | 0.53620 (9) | 1.34412 (8) | 0.02313 (17) | |
F12 | 0.18252 (8) | 0.32907 (9) | 1.54950 (8) | 0.03013 (17) | |
O1 | 0.09274 (10) | 0.60128 (10) | 0.76376 (8) | 0.02489 (18) | |
C24 | −0.47257 (14) | −0.00009 (12) | 0.64633 (10) | 0.0204 (2) | |
C3 | 0.13028 (13) | 0.58530 (12) | 0.91000 (10) | 0.0196 (2) | |
C5 | 0.05022 (13) | 0.66421 (12) | 0.99688 (11) | 0.0204 (2) | |
C13 | 0.34702 (13) | 0.44886 (12) | 1.37978 (11) | 0.0197 (2) | |
C23 | −0.65179 (13) | −0.09123 (12) | 0.56684 (11) | 0.0197 (2) | |
C12 | 0.27270 (14) | 0.29858 (13) | 1.27786 (12) | 0.0235 (2) | |
C25 | −0.34131 (13) | 0.07603 (12) | 0.58808 (11) | 0.0205 (2) | |
C14 | 0.52767 (13) | 0.54587 (13) | 1.36766 (11) | 0.0212 (2) | |
C15 | 0.34023 (13) | 0.40981 (12) | 1.52821 (11) | 0.0207 (2) | |
C4 | 0.06470 (13) | 0.40977 (13) | 0.92853 (11) | 0.0205 (2) | |
C22 | −0.76156 (14) | −0.02754 (13) | 0.62251 (12) | 0.0246 (2) | |
C1 | 0.46278 (16) | 0.73049 (19) | 0.99717 (14) | 0.0373 (3) | |
C2 | 0.31531 (14) | 0.66562 (14) | 0.95594 (11) | 0.0248 (2) | |
C21 | −0.85068 (17) | 0.02473 (16) | 0.66346 (15) | 0.0344 (3) | |
C11 | 0.21624 (16) | 0.17711 (15) | 1.19891 (14) | 0.0305 (2) | |
H11A | 0.264 (2) | 0.601 (2) | 1.417 (2) | 0.041 (5)* | |
H11 | 0.175 (2) | 0.081 (2) | 1.137 (2) | 0.046 (5)* | |
H21A | −0.758 (3) | −0.281 (2) | 0.642 (2) | 0.050 (5)* | |
H21 | −0.924 (3) | 0.069 (2) | 0.692 (2) | 0.053 (5)* | |
H1A | −0.018 (3) | 0.560 (2) | 0.735 (2) | 0.051 (5)* | |
H1 | 0.582 (3) | 0.786 (3) | 1.037 (2) | 0.067 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0307 (4) | 0.0319 (4) | 0.0319 (4) | 0.0169 (3) | 0.0119 (3) | −0.0009 (3) |
F2 | 0.0314 (4) | 0.0187 (3) | 0.0331 (4) | 0.0082 (3) | 0.0060 (3) | 0.0056 (3) |
F21 | 0.0346 (4) | 0.0356 (4) | 0.0164 (3) | 0.0145 (3) | 0.0058 (3) | 0.0063 (3) |
F11 | 0.0311 (4) | 0.0410 (4) | 0.0206 (3) | 0.0133 (3) | 0.0069 (3) | 0.0122 (3) |
O21 | 0.0300 (4) | 0.0176 (3) | 0.0255 (4) | 0.0088 (3) | 0.0130 (3) | 0.0059 (3) |
F22 | 0.0207 (3) | 0.0316 (4) | 0.0273 (3) | 0.0064 (3) | −0.0014 (3) | 0.0024 (3) |
O11 | 0.0241 (4) | 0.0240 (4) | 0.0232 (4) | 0.0143 (3) | −0.0007 (3) | 0.0011 (3) |
F12 | 0.0187 (3) | 0.0355 (4) | 0.0327 (4) | 0.0066 (3) | 0.0080 (3) | 0.0098 (3) |
O1 | 0.0205 (4) | 0.0346 (4) | 0.0173 (3) | 0.0086 (3) | 0.0050 (3) | 0.0079 (3) |
C24 | 0.0248 (5) | 0.0208 (5) | 0.0164 (4) | 0.0104 (4) | 0.0038 (4) | 0.0036 (3) |
C3 | 0.0186 (4) | 0.0234 (5) | 0.0167 (4) | 0.0079 (4) | 0.0049 (3) | 0.0049 (3) |
C5 | 0.0210 (5) | 0.0184 (4) | 0.0205 (4) | 0.0075 (4) | 0.0028 (4) | 0.0029 (3) |
C13 | 0.0194 (4) | 0.0201 (4) | 0.0200 (4) | 0.0098 (4) | 0.0015 (3) | 0.0028 (3) |
C23 | 0.0212 (5) | 0.0178 (4) | 0.0206 (5) | 0.0080 (4) | 0.0066 (4) | 0.0045 (3) |
C12 | 0.0223 (5) | 0.0248 (5) | 0.0245 (5) | 0.0118 (4) | 0.0031 (4) | 0.0032 (4) |
C25 | 0.0200 (5) | 0.0198 (4) | 0.0198 (4) | 0.0074 (4) | 0.0015 (4) | 0.0024 (3) |
C14 | 0.0233 (5) | 0.0225 (5) | 0.0194 (5) | 0.0104 (4) | 0.0057 (4) | 0.0060 (4) |
C15 | 0.0184 (5) | 0.0211 (5) | 0.0232 (5) | 0.0080 (4) | 0.0059 (4) | 0.0053 (4) |
C4 | 0.0211 (5) | 0.0224 (5) | 0.0190 (4) | 0.0106 (4) | 0.0046 (4) | 0.0010 (4) |
C22 | 0.0244 (5) | 0.0222 (5) | 0.0276 (5) | 0.0090 (4) | 0.0086 (4) | 0.0048 (4) |
C1 | 0.0224 (6) | 0.0503 (8) | 0.0322 (6) | 0.0081 (5) | 0.0046 (5) | 0.0132 (5) |
C2 | 0.0221 (5) | 0.0298 (5) | 0.0214 (5) | 0.0089 (4) | 0.0061 (4) | 0.0076 (4) |
C21 | 0.0345 (6) | 0.0317 (6) | 0.0445 (7) | 0.0177 (5) | 0.0180 (5) | 0.0079 (5) |
C11 | 0.0312 (6) | 0.0276 (6) | 0.0313 (6) | 0.0130 (5) | 0.0029 (5) | −0.0010 (4) |
F1—C4 | 1.3455 (12) | C3—C2 | 1.4775 (16) |
F1—F22 | 2.8649 (17) | C3—C5 | 1.5091 (15) |
F2—C5 | 1.3464 (12) | C3—C4 | 1.5128 (15) |
F2—F1i | 2.6873 (14) | C5—C4i | 1.3203 (16) |
F21—C24 | 1.3386 (12) | C13—C12 | 1.4833 (16) |
F11—C14 | 1.3378 (12) | C13—C15 | 1.5069 (14) |
F11—F1ii | 2.9527 (13) | C13—C14 | 1.5099 (15) |
O21—C23 | 1.4361 (13) | C23—C22 | 1.4782 (15) |
O21—H21A | 0.81 (2) | C23—C25v | 1.5084 (14) |
F22—C25 | 1.3487 (13) | C12—C11 | 1.1832 (18) |
O11—C13 | 1.4384 (12) | C25—C23v | 1.5084 (14) |
O11—H11A | 0.851 (19) | C14—C15iii | 1.3238 (16) |
F12—C15 | 1.3453 (13) | C15—C14iii | 1.3238 (16) |
F12—F11iii | 2.7098 (15) | C4—C5i | 1.3203 (15) |
F12—F1iv | 16.294 (3) | C22—C21 | 1.1862 (18) |
O1—C3 | 1.4348 (12) | C1—C2 | 1.1829 (18) |
O1—H1A | 0.88 (2) | C1—H1 | 0.97 (2) |
C24—C25 | 1.3221 (15) | C21—H21 | 0.96 (2) |
C24—C23 | 1.5085 (16) | C11—H11 | 0.936 (19) |
C4—F1—F22 | 90.58 (6) | C12—C13—C14 | 109.47 (9) |
C5—F2—F1i | 59.41 (6) | C15—C13—C14 | 109.63 (9) |
C14—F11—F1ii | 122.52 (7) | O21—C23—C22 | 111.66 (9) |
C23—O21—H21A | 109.3 (14) | O21—C23—C24 | 108.92 (9) |
C25—F22—F1 | 173.72 (7) | C22—C23—C24 | 110.27 (9) |
C13—O11—H11A | 107.3 (12) | O21—C23—C25v | 106.61 (9) |
C15—F12—F11iii | 58.65 (6) | C22—C23—C25v | 109.85 (9) |
C15—F12—F1iv | 71.00 (7) | C24—C23—C25v | 109.46 (9) |
F11iii—F12—F1iv | 128.58 (3) | C11—C12—C13 | 178.10 (12) |
C3—O1—H1A | 109.4 (13) | C24—C25—F22 | 120.83 (10) |
C25—C24—F21 | 121.05 (10) | C24—C25—C23v | 125.41 (10) |
C25—C24—C23 | 125.09 (9) | F22—C25—C23v | 113.74 (9) |
F21—C24—C23 | 113.84 (9) | C15iii—C14—F11 | 120.87 (10) |
O1—C3—C2 | 107.20 (9) | C15iii—C14—C13 | 125.11 (10) |
O1—C3—C5 | 110.26 (9) | F11—C14—C13 | 114.01 (9) |
C2—C3—C5 | 109.96 (9) | C14iii—C15—F12 | 121.33 (10) |
O1—C3—C4 | 110.33 (9) | C14iii—C15—C13 | 125.25 (10) |
C2—C3—C4 | 110.07 (9) | F12—C15—C13 | 113.36 (9) |
C5—C3—C4 | 109.02 (8) | C5i—C4—F1 | 120.41 (10) |
C4i—C5—F2 | 120.64 (10) | C5i—C4—C3 | 125.46 (10) |
C4i—C5—C3 | 125.45 (10) | F1—C4—C3 | 114.12 (9) |
F2—C5—C3 | 113.89 (9) | C21—C22—C23 | 178.11 (13) |
O11—C13—C12 | 107.14 (9) | C2—C1—H1 | 176.3 (13) |
O11—C13—C15 | 109.96 (9) | C1—C2—C3 | 177.83 (12) |
C12—C13—C15 | 110.04 (9) | C22—C21—H21 | 177.2 (12) |
O11—C13—C14 | 110.57 (9) | C12—C11—H11 | 178.4 (11) |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+2; (iii) −x+1, −y+1, −z+3; (iv) x, y, z−1; (v) −x−1, −y, −z+1. |
C10H4Cl4O2 | Dx = 1.590 Mg m−3 |
Mr = 297.93 | Melting point = 205–206 K |
Tetragonal, I41/a | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -I 4ad | Cell parameters from 505 reflections |
a = 16.758 (2) Å | θ = 5.3–25.3° |
c = 8.865 (2) Å | µ = 0.93 mm−1 |
V = 2489.6 (7) Å3 | T = 150 K |
Z = 8 | Block, colourless |
F(000) = 1184 | 0.3 × 0.3 × 0.2 mm |
Bruker SMART CCD diffractometer | 1421 independent reflections |
Radiation source: fine-focus sealed tube | 1202 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: not relevant pixels mm-1 | θmax = 27.4°, θmin = 2.4° |
ω scans | h = −21→20 |
Absorption correction: multi-scan SADABS (Sheldrick 1996) | k = −21→19 |
Tmin = 0.665, Tmax = 0.830 | l = −9→11 |
8404 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | All H-atom parameters refined |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0383P)2 + 5.8833P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
1421 reflections | Δρmax = 0.59 e Å−3 |
82 parameters | Δρmin = −0.44 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0178 (11) |
C10H4Cl4O2 | Z = 8 |
Mr = 297.93 | Mo Kα radiation |
Tetragonal, I41/a | µ = 0.93 mm−1 |
a = 16.758 (2) Å | T = 150 K |
c = 8.865 (2) Å | 0.3 × 0.3 × 0.2 mm |
V = 2489.6 (7) Å3 |
Bruker SMART CCD diffractometer | 1421 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick 1996) | 1202 reflections with I > 2σ(I) |
Tmin = 0.665, Tmax = 0.830 | Rint = 0.043 |
8404 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.125 | All H-atom parameters refined |
S = 1.09 | Δρmax = 0.59 e Å−3 |
1421 reflections | Δρmin = −0.44 e Å−3 |
82 parameters |
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 | ||
Cl1 | 0.77134 (5) | 0.61807 (5) | −0.00252 (9) | 0.0642 (3) | |
Cl2 | 0.61323 (6) | 0.71900 (6) | −0.01517 (12) | 0.0813 (4) | |
O1 | 0.89228 (11) | 0.72875 (11) | −0.1540 (3) | 0.0533 (6) | |
C4 | 0.75598 (14) | 0.69120 (14) | −0.1362 (3) | 0.0379 (6) | |
C5 | 0.68998 (14) | 0.73415 (15) | −0.1411 (3) | 0.0402 (6) | |
C2 | 0.84570 (16) | 0.62493 (16) | −0.3155 (3) | 0.0462 (6) | |
C3 | 0.82653 (13) | 0.70177 (13) | −0.2419 (3) | 0.0363 (6) | |
C1 | 0.8625 (2) | 0.5634 (2) | −0.3678 (5) | 0.0714 (10) | |
HA | 0.922 (2) | 0.696 (2) | −0.136 (4) | 0.060 (10)* | |
H1 | 0.876 (3) | 0.517 (3) | −0.407 (6) | 0.112 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0768 (6) | 0.0581 (5) | 0.0576 (5) | 0.0093 (4) | −0.0049 (4) | 0.0228 (4) |
Cl2 | 0.0696 (6) | 0.0783 (6) | 0.0961 (8) | 0.0109 (4) | 0.0469 (5) | 0.0194 (5) |
O1 | 0.0353 (10) | 0.0313 (9) | 0.0934 (16) | 0.0033 (7) | −0.0256 (10) | −0.0102 (10) |
C4 | 0.0398 (13) | 0.0349 (12) | 0.0388 (13) | 0.0001 (9) | −0.0047 (10) | 0.0033 (10) |
C5 | 0.0342 (12) | 0.0391 (13) | 0.0473 (14) | −0.0003 (9) | 0.0061 (10) | 0.0012 (10) |
C2 | 0.0417 (14) | 0.0389 (14) | 0.0579 (16) | 0.0025 (11) | −0.0049 (12) | −0.0067 (12) |
C3 | 0.0272 (11) | 0.0311 (11) | 0.0505 (14) | 0.0012 (9) | −0.0062 (10) | −0.0037 (10) |
C1 | 0.090 (3) | 0.0497 (19) | 0.074 (2) | 0.0115 (18) | −0.004 (2) | −0.0184 (17) |
Cl1—C4 | 1.724 (2) | C5—C3i | 1.518 (3) |
Cl2—C5 | 1.722 (3) | C2—C1 | 1.165 (4) |
O1—C3 | 1.423 (3) | C2—C3 | 1.479 (3) |
O1—HA | 0.76 (4) | C3—C5i | 1.518 (3) |
C4—C5 | 1.320 (3) | C1—H1 | 0.88 (5) |
C4—C3 | 1.519 (3) | ||
C3—O1—HA | 113 (3) | O1—C3—C2 | 110.49 (19) |
C5—C4—C3 | 124.6 (2) | O1—C3—C5i | 106.88 (19) |
C5—C4—Cl1 | 122.4 (2) | C2—C3—C5i | 110.7 (2) |
C3—C4—Cl1 | 113.00 (17) | O1—C3—C4 | 107.6 (2) |
C4—C5—C3i | 124.1 (2) | C2—C3—C4 | 109.9 (2) |
C4—C5—Cl2 | 121.6 (2) | C5i—C3—C4 | 111.22 (18) |
C3i—C5—Cl2 | 114.27 (17) | C2—C1—H1 | 179 (3) |
C1—C2—C3 | 177.0 (3) |
Symmetry code: (i) −x+3/2, −y+3/2, −z−1/2. |
C10H4Br4O2 | F(000) = 880 |
Mr = 475.77 | Dx = 2.477 Mg m−3 |
Triclinic, P1 | Melting point = 205–206 K |
a = 8.9147 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.6402 (5) Å | Cell parameters from 510 reflections |
c = 12.6547 (5) Å | θ = 5.1–23.7° |
α = 85.738 (1)° | µ = 12.60 mm−1 |
β = 69.625 (1)° | T = 150 K |
γ = 72.72 (1)° | Block, colourless |
V = 1275.76 (8) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 4 |
Bruker SMART CCD diffractometer | 5818 independent reflections |
Radiation source: fine-focus sealed tube | 4966 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: not relevant pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ω scans | h = −11→11 |
Absorption correction: multi-scan SADABS (Sheldrick 1996) | k = −16→16 |
Tmin = 0.018, Tmax = 0.074 | l = −16→16 |
14367 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)] = 0.034 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.078 | All H-atom parameters refined |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0218P)2 + 4.0324P] where P = (Fo2 + 2Fc2)/3 |
5818 reflections | (Δ/σ)max = 0.005 |
321 parameters | Δρmax = 0.80 e Å−3 |
0 restraints | Δρmin = −1.05 e Å−3 |
C10H4Br4O2 | γ = 72.72 (1)° |
Mr = 475.77 | V = 1275.76 (8) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.9147 (3) Å | Mo Kα radiation |
b = 12.6402 (5) Å | µ = 12.60 mm−1 |
c = 12.6547 (5) Å | T = 150 K |
α = 85.738 (1)° | 0.3 × 0.2 × 0.2 mm |
β = 69.625 (1)° |
Bruker SMART CCD diffractometer | 5818 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick 1996) | 4966 reflections with I > 2σ(I) |
Tmin = 0.018, Tmax = 0.074 | Rint = 0.043 |
14367 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.078 | All H-atom parameters refined |
S = 1.15 | Δρmax = 0.80 e Å−3 |
5818 reflections | Δρmin = −1.05 e Å−3 |
321 parameters |
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 | ||
Br32 | 0.23387 (6) | 0.17095 (4) | 0.93445 (4) | 0.02955 (11) | |
Br21 | 0.26974 (6) | 0.38542 (4) | 1.13043 (4) | 0.02820 (11) | |
Br22 | 0.40392 (6) | 0.42595 (5) | 0.85341 (4) | 0.03255 (12) | |
Br11 | 0.78564 (6) | 0.43745 (4) | 0.62350 (4) | 0.03124 (12) | |
Br31 | 0.40744 (6) | −0.09732 (4) | 0.86395 (4) | 0.02761 (11) | |
Br1 | 0.79084 (7) | −0.18445 (4) | 0.59429 (4) | 0.03404 (12) | |
Br2 | 0.84216 (7) | −0.08758 (5) | 0.33470 (4) | 0.03575 (13) | |
Br12 | 0.48669 (6) | 0.68322 (4) | 0.67843 (4) | 0.02516 (10) | |
O3 | −0.0988 (4) | 0.3802 (3) | 1.1712 (3) | 0.0233 (7) | |
O1 | 1.0803 (5) | −0.1357 (3) | 0.6498 (3) | 0.0273 (7) | |
C34 | 0.1752 (5) | −0.0377 (3) | 0.9406 (3) | 0.0187 (8) | |
C25 | 0.1746 (5) | 0.4672 (3) | 0.9417 (4) | 0.0183 (8) | |
C4 | 0.9092 (5) | −0.0793 (4) | 0.5363 (4) | 0.0218 (9) | |
C13 | 0.6262 (5) | 0.3856 (3) | 0.4816 (3) | 0.0186 (8) | |
C3 | 0.9714 (5) | −0.0412 (3) | 0.6199 (3) | 0.0185 (8) | |
C5 | 0.9306 (6) | −0.0423 (4) | 0.4334 (4) | 0.0215 (9) | |
C35 | 0.1068 (5) | 0.0694 (3) | 0.9688 (3) | 0.0187 (8) | |
C14 | 0.6176 (5) | 0.4770 (4) | 0.5572 (3) | 0.0178 (8) | |
C15 | 0.5043 (5) | 0.5748 (4) | 0.5760 (3) | 0.0183 (8) | |
C23 | −0.0620 (5) | 0.4806 (3) | 1.1266 (3) | 0.0182 (8) | |
C33 | 0.0778 (5) | −0.1231 (3) | 0.9671 (3) | 0.0163 (8) | |
C24 | 0.1214 (5) | 0.4505 (3) | 1.0519 (3) | 0.0187 (8) | |
O4 | 0.0960 (4) | −0.1677 (3) | 0.8614 (2) | 0.0207 (6) | |
O2 | 0.7898 (4) | 0.3546 (3) | 0.3984 (3) | 0.0202 (6) | |
C22 | −0.0946 (5) | 0.5578 (3) | 1.2199 (4) | 0.0201 (8) | |
C2 | 0.8281 (6) | 0.0123 (4) | 0.7218 (4) | 0.0240 (9) | |
C32 | 0.1482 (6) | −0.2131 (4) | 1.0344 (4) | 0.0222 (9) | |
C21 | −0.1280 (6) | 0.6166 (4) | 1.2985 (4) | 0.0268 (10) | |
C12 | 0.5913 (6) | 0.2906 (4) | 0.5515 (4) | 0.0233 (9) | |
C1 | 0.7190 (7) | 0.0528 (5) | 0.8056 (4) | 0.0330 (11) | |
C11 | 0.5609 (7) | 0.2152 (5) | 0.6053 (5) | 0.0385 (13) | |
C31 | 0.2033 (8) | −0.2869 (5) | 1.0836 (5) | 0.0367 (13) | |
H1A | 1.056 (8) | −0.133 (5) | 0.708 (6) | 0.038 (19)* | |
H1 | 0.632 (8) | 0.085 (5) | 0.867 (6) | 0.047 (18)* | |
H4A | 0.094 (7) | −0.229 (5) | 0.869 (5) | 0.030 (15)* | |
H11 | 0.561 (8) | 0.153 (5) | 0.633 (5) | 0.045 (18)* | |
H21 | −0.158 (8) | 0.673 (5) | 1.357 (5) | 0.045 (17)* | |
H4 | 0.240 (8) | −0.334 (5) | 1.109 (5) | 0.040 (19)* | |
H3A | −0.141 (8) | 0.378 (5) | 1.225 (5) | 0.029 (17)* | |
H2A | 0.786 (13) | 0.306 (8) | 0.390 (8) | 0.10 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br32 | 0.0236 (2) | 0.0204 (2) | 0.0428 (3) | −0.00980 (17) | −0.0054 (2) | −0.00317 (19) |
Br21 | 0.0283 (2) | 0.0327 (2) | 0.0253 (2) | −0.00188 (19) | −0.01715 (19) | 0.00119 (18) |
Br22 | 0.0175 (2) | 0.0510 (3) | 0.0243 (2) | −0.0069 (2) | −0.00360 (18) | 0.0001 (2) |
Br11 | 0.0227 (2) | 0.0446 (3) | 0.0255 (2) | 0.0005 (2) | −0.01414 (19) | −0.0070 (2) |
Br31 | 0.0182 (2) | 0.0242 (2) | 0.0356 (3) | −0.00451 (17) | −0.00288 (18) | −0.00867 (18) |
Br1 | 0.0450 (3) | 0.0365 (3) | 0.0266 (2) | −0.0273 (2) | −0.0071 (2) | 0.0038 (2) |
Br2 | 0.0476 (3) | 0.0472 (3) | 0.0276 (2) | −0.0274 (3) | −0.0204 (2) | 0.0041 (2) |
Br12 | 0.0257 (2) | 0.0266 (2) | 0.0248 (2) | −0.00922 (18) | −0.00736 (18) | −0.00823 (17) |
O3 | 0.0328 (18) | 0.0211 (16) | 0.0135 (15) | −0.0121 (14) | −0.0015 (14) | 0.0018 (12) |
O1 | 0.038 (2) | 0.0239 (17) | 0.0175 (17) | −0.0022 (14) | −0.0113 (15) | −0.0002 (13) |
C34 | 0.017 (2) | 0.022 (2) | 0.0153 (19) | −0.0047 (16) | −0.0045 (16) | −0.0016 (15) |
C25 | 0.0150 (19) | 0.019 (2) | 0.020 (2) | −0.0041 (16) | −0.0050 (16) | −0.0008 (16) |
C4 | 0.020 (2) | 0.022 (2) | 0.022 (2) | −0.0086 (17) | −0.0025 (17) | −0.0024 (17) |
C13 | 0.021 (2) | 0.020 (2) | 0.0146 (19) | −0.0061 (17) | −0.0056 (16) | 0.0009 (15) |
C3 | 0.020 (2) | 0.018 (2) | 0.018 (2) | −0.0048 (16) | −0.0077 (16) | 0.0010 (15) |
C5 | 0.024 (2) | 0.024 (2) | 0.019 (2) | −0.0083 (17) | −0.0087 (17) | −0.0006 (16) |
C35 | 0.022 (2) | 0.020 (2) | 0.0161 (19) | −0.0084 (17) | −0.0070 (16) | −0.0005 (15) |
C14 | 0.0172 (19) | 0.024 (2) | 0.0134 (18) | −0.0065 (16) | −0.0059 (16) | 0.0009 (15) |
C15 | 0.019 (2) | 0.022 (2) | 0.0155 (19) | −0.0088 (16) | −0.0046 (16) | −0.0016 (15) |
C23 | 0.022 (2) | 0.0175 (19) | 0.0157 (19) | −0.0060 (16) | −0.0082 (17) | 0.0024 (15) |
C33 | 0.019 (2) | 0.0131 (18) | 0.0165 (19) | −0.0029 (15) | −0.0072 (16) | −0.0026 (15) |
C24 | 0.019 (2) | 0.019 (2) | 0.019 (2) | −0.0057 (16) | −0.0076 (17) | −0.0011 (16) |
O4 | 0.0311 (17) | 0.0153 (15) | 0.0172 (14) | −0.0073 (13) | −0.0097 (13) | −0.0001 (11) |
O2 | 0.0181 (15) | 0.0212 (16) | 0.0173 (15) | −0.0041 (12) | −0.0022 (12) | −0.0014 (12) |
C22 | 0.021 (2) | 0.018 (2) | 0.022 (2) | −0.0057 (16) | −0.0088 (17) | 0.0032 (16) |
C2 | 0.024 (2) | 0.029 (2) | 0.021 (2) | −0.0078 (18) | −0.0100 (19) | −0.0002 (18) |
C32 | 0.022 (2) | 0.022 (2) | 0.023 (2) | −0.0065 (18) | −0.0080 (18) | 0.0002 (17) |
C21 | 0.029 (2) | 0.027 (2) | 0.025 (2) | −0.0069 (19) | −0.011 (2) | −0.0051 (19) |
C12 | 0.022 (2) | 0.023 (2) | 0.021 (2) | −0.0043 (17) | −0.0055 (18) | 0.0027 (17) |
C1 | 0.026 (3) | 0.045 (3) | 0.024 (2) | −0.007 (2) | −0.005 (2) | −0.006 (2) |
C11 | 0.035 (3) | 0.033 (3) | 0.037 (3) | −0.008 (2) | −0.004 (2) | 0.010 (2) |
C31 | 0.040 (3) | 0.033 (3) | 0.043 (3) | −0.009 (2) | −0.025 (3) | 0.015 (2) |
Br32—C35 | 1.886 (4) | C3—C2 | 1.491 (6) |
Br21—C24 | 1.887 (4) | C3—C5iii | 1.537 (6) |
Br22—C25 | 1.888 (4) | C5—C3iii | 1.537 (6) |
Br11—C14 | 1.889 (4) | C35—C33iv | 1.522 (6) |
Br31—C34 | 1.892 (4) | C14—C15 | 1.319 (6) |
Br1—C4 | 1.889 (4) | C15—C13ii | 1.525 (6) |
Br2—C5 | 1.889 (4) | C23—C22 | 1.481 (6) |
Br12—C15 | 1.891 (4) | C23—C25i | 1.522 (6) |
O3—C23 | 1.431 (5) | C23—C24 | 1.523 (6) |
O3—H3A | 0.66 (6) | C33—O4 | 1.428 (5) |
O1—C3 | 1.419 (5) | C33—C32 | 1.488 (6) |
O1—H1A | 0.69 (6) | C33—C35iv | 1.522 (6) |
C34—C35 | 1.329 (6) | O4—H4A | 0.78 (6) |
C34—C33 | 1.526 (6) | O2—H2A | 0.64 (9) |
C25—C24 | 1.330 (6) | C22—C21 | 1.185 (6) |
C25—C23i | 1.522 (6) | C2—C1 | 1.183 (7) |
C4—C5 | 1.318 (6) | C32—C31 | 1.164 (7) |
C4—C3 | 1.517 (6) | C21—H21 | 0.98 (6) |
C13—O2 | 1.429 (5) | C12—C11 | 1.172 (7) |
C13—C12 | 1.481 (6) | C1—H1 | 0.90 (7) |
C13—C14 | 1.522 (6) | C11—H11 | 0.83 (7) |
C13—C15ii | 1.525 (6) | C31—H4 | 0.70 (7) |
C23—O3—H3A | 120 (5) | C15—C14—Br11 | 122.4 (3) |
C3—O1—H1A | 106 (5) | C13—C14—Br11 | 113.5 (3) |
C35—C34—C33 | 124.3 (4) | C14—C15—C13ii | 124.6 (4) |
C35—C34—Br31 | 121.5 (3) | C14—C15—Br12 | 123.3 (3) |
C33—C34—Br31 | 114.2 (3) | C13ii—C15—Br12 | 112.1 (3) |
C24—C25—C23i | 125.0 (4) | O3—C23—C22 | 110.0 (3) |
C24—C25—Br22 | 122.0 (3) | O3—C23—C25i | 107.9 (3) |
C23i—C25—Br22 | 112.9 (3) | C22—C23—C25i | 109.8 (3) |
C5—C4—C3 | 124.5 (4) | O3—C23—C24 | 107.7 (3) |
C5—C4—Br1 | 122.0 (3) | C22—C23—C24 | 110.6 (4) |
C3—C4—Br1 | 113.5 (3) | C25i—C23—C24 | 110.8 (3) |
O2—C13—C12 | 111.3 (4) | O4—C33—C32 | 109.9 (3) |
O2—C13—C14 | 107.8 (3) | O4—C33—C35iv | 109.2 (3) |
C12—C13—C14 | 109.0 (3) | C32—C33—C35iv | 109.8 (3) |
O2—C13—C15ii | 109.7 (3) | O4—C33—C34 | 106.7 (3) |
C12—C13—C15ii | 108.0 (4) | C32—C33—C34 | 110.1 (3) |
C14—C13—C15ii | 111.1 (3) | C35iv—C33—C34 | 111.1 (3) |
O1—C3—C2 | 110.5 (4) | C25—C24—C23 | 124.1 (4) |
O1—C3—C4 | 107.8 (3) | C25—C24—Br21 | 122.3 (3) |
C2—C3—C4 | 110.4 (4) | C23—C24—Br21 | 113.5 (3) |
O1—C3—C5iii | 108.6 (4) | C33—O4—H4A | 108 (4) |
C2—C3—C5iii | 108.8 (3) | C13—O2—H2A | 93 (9) |
C4—C3—C5iii | 110.8 (3) | C21—C22—C23 | 176.0 (5) |
C4—C5—C3iii | 124.7 (4) | C1—C2—C3 | 176.9 (5) |
C4—C5—Br2 | 122.9 (3) | C31—C32—C33 | 176.9 (5) |
C3iii—C5—Br2 | 112.5 (3) | C22—C21—H21 | 173 (4) |
C34—C35—C33iv | 124.7 (4) | C11—C12—C13 | 178.2 (6) |
C34—C35—Br32 | 122.3 (3) | C2—C1—H1 | 177 (4) |
C33iv—C35—Br32 | 113.0 (3) | C12—C11—H11 | 167 (5) |
C15—C14—C13 | 124.1 (4) | C32—C31—H4 | 175 (6) |
Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y, −z+1; (iv) −x, −y, −z+2. |
Experimental details
(7) | (8) | (9) | |
Crystal data | |||
Chemical formula | C10H4F4O2 | C10H4Cl4O2 | C10H4Br4O2 |
Mr | 232.13 | 297.93 | 475.77 |
Crystal system, space group | Triclinic, P1 | Tetragonal, I41/a | Triclinic, P1 |
Temperature (K) | 150 | 150 | 150 |
a, b, c (Å) | 8.9002 (18), 9.2388 (18), 9.6721 (19) | 16.758 (2), 16.758 (2), 8.865 (2) | 8.9147 (3), 12.6402 (5), 12.6547 (5) |
α, β, γ (°) | 93.73 (3), 98.73 (3), 114.46 (3) | 90, 90, 90 | 85.738 (1), 69.625 (1), 72.72 (1) |
V (Å3) | 708.3 (2) | 2489.6 (7) | 1275.76 (8) |
Z | 3 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.17 | 0.93 | 12.60 |
Crystal size (mm) | 0.7 × 0.3 × 0.2 | 0.3 × 0.3 × 0.2 | 0.3 × 0.2 × 0.2 |
Data collection | |||
Diffractometer | Bruker SMART CCD diffractometer | Bruker SMART CCD diffractometer | Bruker SMART CCD diffractometer |
Absorption correction | Empirical (using intensity measurements) (XPREP in SHELX97; Sheldrick, 1997) | Multi-scan SADABS (Sheldrick 1996) | Multi-scan SADABS (Sheldrick 1996) |
Tmin, Tmax | 0.289, 0.382 | 0.665, 0.830 | 0.018, 0.074 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8674, 3722, 3376 | 8404, 1421, 1202 | 14367, 5818, 4966 |
Rint | 0.029 | 0.043 | 0.043 |
(sin θ/λ)max (Å−1) | 0.701 | 0.647 | 0.649 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.093, 1.03 | 0.049, 0.125, 1.09 | 0.034, 0.078, 1.15 |
No. of reflections | 3722 | 1421 | 5818 |
No. of parameters | 242 | 82 | 321 |
H-atom treatment | All H-atom parameters refined | All H-atom parameters refined | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.46, −0.24 | 0.59, −0.44 | 0.80, −1.05 |
Computer programs: Bruker SMART (Bruker Systems Inc., 1999a), Bruker SAINT (Bruker Systems Inc., 1999b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).
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