Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Structures of the title compounds are all mediated by strong cooperative arrangements of O—H...O hydrogen bonds, supported by a variety of weaker interactions which affect the type of O—H...O synthon that is formed. The tetrafluoro compound contains hexameric O—H...O synthons in a supramolecular chair conformation, together with C≡C—H...F interactions. However, the tetrachloro and tetrabromo compounds both form tetrameric O—H...O synthons. This dominant pattern is supported by halogen...halogen interactions having one C—Cl[Br]...Cl[Br] angle close to 180° and the other close to 90°, and by C≡C—H...Cl[Br] interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100011496/bm0033sup1.cif
Contains datablocks global, 7, 8, 9

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100011496/bm00337sup2.hkl
Contains datablock 7

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100011496/bm00338sup3.hkl
Contains datablock 8

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768100011496/bm00339sup4.hkl
Contains datablock 9

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768100011496/bm0033sup5.pdf
Supplementary material

CCDC references: 156667; 156668; 156669

Computing details top

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).

(7) 2,3,5,6-tetrafluoro-trans-1,4-diethynyl-cyclohexa-2,5-diene-1,4-diol top
Crystal data top
C10H4F4O2F(000) = 348
Mr = 232.13Dx = 1.633 Mg m3
Triclinic, P1Melting point = 132–133 K
a = 8.9002 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.2388 (18) ÅCell parameters from 999 reflections
c = 9.6721 (19) Åθ = 0.2–30.6°
α = 93.73 (3)°µ = 0.17 mm1
β = 98.73 (3)°T = 150 K
γ = 114.46 (3)°Block, colourless
V = 708.3 (2) Å30.7 × 0.3 × 0.2 mm
Z = 3
Data collection top
Bruker SMART CCD
diffractometer
3722 independent reflections
Radiation source: fine-focus sealed tube3376 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: not relevant pixels mm-1θmax = 29.9°, θmin = 2.2°
ω scansh = 1212
Absorption correction: empirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)
k = 1212
Tmin = 0.289, Tmax = 0.382l = 1313
8674 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034All 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 reflectionsΔρmax = 0.46 e Å3
242 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.080 (5)
Crystal data top
C10H4F4O2γ = 114.46 (3)°
Mr = 232.13V = 708.3 (2) Å3
Triclinic, P1Z = 3
a = 8.9002 (18) ÅMo Kα radiation
b = 9.2388 (18) ŵ = 0.17 mm1
c = 9.6721 (19) ÅT = 150 K
α = 93.73 (3)°0.7 × 0.3 × 0.2 mm
β = 98.73 (3)°
Data collection top
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 = 0.382Rint = 0.029
8674 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.093All H-atom parameters refined
S = 1.03Δρmax = 0.46 e Å3
3722 reflectionsΔρmin = 0.24 e Å3
242 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.13140 (9)0.32812 (9)0.85824 (8)0.02992 (17)
F20.10278 (9)0.82232 (8)0.99013 (8)0.02855 (17)
F210.45397 (9)0.00542 (9)0.78559 (7)0.02882 (17)
F110.54677 (9)0.58373 (9)1.23827 (7)0.03106 (18)
O210.70633 (11)0.25896 (9)0.57778 (9)0.02384 (17)
F220.18494 (8)0.15228 (9)0.66778 (7)0.02902 (17)
O110.24851 (10)0.53620 (9)1.34412 (8)0.02313 (17)
F120.18252 (8)0.32907 (9)1.54950 (8)0.03013 (17)
O10.09274 (10)0.60128 (10)0.76376 (8)0.02489 (18)
C240.47257 (14)0.00009 (12)0.64633 (10)0.0204 (2)
C30.13028 (13)0.58530 (12)0.91000 (10)0.0196 (2)
C50.05022 (13)0.66421 (12)0.99688 (11)0.0204 (2)
C130.34702 (13)0.44886 (12)1.37978 (11)0.0197 (2)
C230.65179 (13)0.09123 (12)0.56684 (11)0.0197 (2)
C120.27270 (14)0.29858 (13)1.27786 (12)0.0235 (2)
C250.34131 (13)0.07603 (12)0.58808 (11)0.0205 (2)
C140.52767 (13)0.54587 (13)1.36766 (11)0.0212 (2)
C150.34023 (13)0.40981 (12)1.52821 (11)0.0207 (2)
C40.06470 (13)0.40977 (13)0.92853 (11)0.0205 (2)
C220.76156 (14)0.02754 (13)0.62251 (12)0.0246 (2)
C10.46278 (16)0.73049 (19)0.99717 (14)0.0373 (3)
C20.31531 (14)0.66562 (14)0.95594 (11)0.0248 (2)
C210.85068 (17)0.02473 (16)0.66346 (15)0.0344 (3)
C110.21624 (16)0.17711 (15)1.19891 (14)0.0305 (2)
H11A0.264 (2)0.601 (2)1.417 (2)0.041 (5)*
H110.175 (2)0.081 (2)1.137 (2)0.046 (5)*
H21A0.758 (3)0.281 (2)0.642 (2)0.050 (5)*
H210.924 (3)0.069 (2)0.692 (2)0.053 (5)*
H1A0.018 (3)0.560 (2)0.735 (2)0.051 (5)*
H10.582 (3)0.786 (3)1.037 (2)0.067 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0307 (4)0.0319 (4)0.0319 (4)0.0169 (3)0.0119 (3)0.0009 (3)
F20.0314 (4)0.0187 (3)0.0331 (4)0.0082 (3)0.0060 (3)0.0056 (3)
F210.0346 (4)0.0356 (4)0.0164 (3)0.0145 (3)0.0058 (3)0.0063 (3)
F110.0311 (4)0.0410 (4)0.0206 (3)0.0133 (3)0.0069 (3)0.0122 (3)
O210.0300 (4)0.0176 (3)0.0255 (4)0.0088 (3)0.0130 (3)0.0059 (3)
F220.0207 (3)0.0316 (4)0.0273 (3)0.0064 (3)0.0014 (3)0.0024 (3)
O110.0241 (4)0.0240 (4)0.0232 (4)0.0143 (3)0.0007 (3)0.0011 (3)
F120.0187 (3)0.0355 (4)0.0327 (4)0.0066 (3)0.0080 (3)0.0098 (3)
O10.0205 (4)0.0346 (4)0.0173 (3)0.0086 (3)0.0050 (3)0.0079 (3)
C240.0248 (5)0.0208 (5)0.0164 (4)0.0104 (4)0.0038 (4)0.0036 (3)
C30.0186 (4)0.0234 (5)0.0167 (4)0.0079 (4)0.0049 (3)0.0049 (3)
C50.0210 (5)0.0184 (4)0.0205 (4)0.0075 (4)0.0028 (4)0.0029 (3)
C130.0194 (4)0.0201 (4)0.0200 (4)0.0098 (4)0.0015 (3)0.0028 (3)
C230.0212 (5)0.0178 (4)0.0206 (5)0.0080 (4)0.0066 (4)0.0045 (3)
C120.0223 (5)0.0248 (5)0.0245 (5)0.0118 (4)0.0031 (4)0.0032 (4)
C250.0200 (5)0.0198 (4)0.0198 (4)0.0074 (4)0.0015 (4)0.0024 (3)
C140.0233 (5)0.0225 (5)0.0194 (5)0.0104 (4)0.0057 (4)0.0060 (4)
C150.0184 (5)0.0211 (5)0.0232 (5)0.0080 (4)0.0059 (4)0.0053 (4)
C40.0211 (5)0.0224 (5)0.0190 (4)0.0106 (4)0.0046 (4)0.0010 (4)
C220.0244 (5)0.0222 (5)0.0276 (5)0.0090 (4)0.0086 (4)0.0048 (4)
C10.0224 (6)0.0503 (8)0.0322 (6)0.0081 (5)0.0046 (5)0.0132 (5)
C20.0221 (5)0.0298 (5)0.0214 (5)0.0089 (4)0.0061 (4)0.0076 (4)
C210.0345 (6)0.0317 (6)0.0445 (7)0.0177 (5)0.0180 (5)0.0079 (5)
C110.0312 (6)0.0276 (6)0.0313 (6)0.0130 (5)0.0029 (5)0.0010 (4)
Geometric parameters (Å, º) top
F1—C41.3455 (12)C3—C21.4775 (16)
F1—F222.8649 (17)C3—C51.5091 (15)
F2—C51.3464 (12)C3—C41.5128 (15)
F2—F1i2.6873 (14)C5—C4i1.3203 (16)
F21—C241.3386 (12)C13—C121.4833 (16)
F11—C141.3378 (12)C13—C151.5069 (14)
F11—F1ii2.9527 (13)C13—C141.5099 (15)
O21—C231.4361 (13)C23—C221.4782 (15)
O21—H21A0.81 (2)C23—C25v1.5084 (14)
F22—C251.3487 (13)C12—C111.1832 (18)
O11—C131.4384 (12)C25—C23v1.5084 (14)
O11—H11A0.851 (19)C14—C15iii1.3238 (16)
F12—C151.3453 (13)C15—C14iii1.3238 (16)
F12—F11iii2.7098 (15)C4—C5i1.3203 (15)
F12—F1iv16.294 (3)C22—C211.1862 (18)
O1—C31.4348 (12)C1—C21.1829 (18)
O1—H1A0.88 (2)C1—H10.97 (2)
C24—C251.3221 (15)C21—H210.96 (2)
C24—C231.5085 (16)C11—H110.936 (19)
C4—F1—F2290.58 (6)C12—C13—C14109.47 (9)
C5—F2—F1i59.41 (6)C15—C13—C14109.63 (9)
C14—F11—F1ii122.52 (7)O21—C23—C22111.66 (9)
C23—O21—H21A109.3 (14)O21—C23—C24108.92 (9)
C25—F22—F1173.72 (7)C22—C23—C24110.27 (9)
C13—O11—H11A107.3 (12)O21—C23—C25v106.61 (9)
C15—F12—F11iii58.65 (6)C22—C23—C25v109.85 (9)
C15—F12—F1iv71.00 (7)C24—C23—C25v109.46 (9)
F11iii—F12—F1iv128.58 (3)C11—C12—C13178.10 (12)
C3—O1—H1A109.4 (13)C24—C25—F22120.83 (10)
C25—C24—F21121.05 (10)C24—C25—C23v125.41 (10)
C25—C24—C23125.09 (9)F22—C25—C23v113.74 (9)
F21—C24—C23113.84 (9)C15iii—C14—F11120.87 (10)
O1—C3—C2107.20 (9)C15iii—C14—C13125.11 (10)
O1—C3—C5110.26 (9)F11—C14—C13114.01 (9)
C2—C3—C5109.96 (9)C14iii—C15—F12121.33 (10)
O1—C3—C4110.33 (9)C14iii—C15—C13125.25 (10)
C2—C3—C4110.07 (9)F12—C15—C13113.36 (9)
C5—C3—C4109.02 (8)C5i—C4—F1120.41 (10)
C4i—C5—F2120.64 (10)C5i—C4—C3125.46 (10)
C4i—C5—C3125.45 (10)F1—C4—C3114.12 (9)
F2—C5—C3113.89 (9)C21—C22—C23178.11 (13)
O11—C13—C12107.14 (9)C2—C1—H1176.3 (13)
O11—C13—C15109.96 (9)C1—C2—C3177.83 (12)
C12—C13—C15110.04 (9)C22—C21—H21177.2 (12)
O11—C13—C14110.57 (9)C12—C11—H11178.4 (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, z1; (v) x1, y, z+1.
(8) 2,3,5,6-tetrachloro-trans-1,4-diethynyl-cyclohexa-2,5-diene-1,4-diol top
Crystal data top
C10H4Cl4O2Dx = 1.590 Mg m3
Mr = 297.93Melting point = 205–206 K
Tetragonal, I41/aMo Kα radiation, λ = 0.71073 Å
Hall symbol: -I 4adCell parameters from 505 reflections
a = 16.758 (2) Åθ = 5.3–25.3°
c = 8.865 (2) ŵ = 0.93 mm1
V = 2489.6 (7) Å3T = 150 K
Z = 8Block, colourless
F(000) = 11840.3 × 0.3 × 0.2 mm
Data collection top
Bruker SMART CCD
diffractometer
1421 independent reflections
Radiation source: fine-focus sealed tube1202 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: not relevant pixels mm-1θmax = 27.4°, θmin = 2.4°
ω scansh = 2120
Absorption correction: multi-scan
SADABS (Sheldrick 1996)
k = 2119
Tmin = 0.665, Tmax = 0.830l = 911
8404 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049All 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 reflectionsΔρmax = 0.59 e Å3
82 parametersΔρmin = 0.44 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0178 (11)
Crystal data top
C10H4Cl4O2Z = 8
Mr = 297.93Mo Kα radiation
Tetragonal, I41/aµ = 0.93 mm1
a = 16.758 (2) ÅT = 150 K
c = 8.865 (2) Å0.3 × 0.3 × 0.2 mm
V = 2489.6 (7) Å3
Data collection top
Bruker SMART CCD
diffractometer
1421 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick 1996)
1202 reflections with I > 2σ(I)
Tmin = 0.665, Tmax = 0.830Rint = 0.043
8404 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.125All H-atom parameters refined
S = 1.09Δρmax = 0.59 e Å3
1421 reflectionsΔρmin = 0.44 e Å3
82 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.77134 (5)0.61807 (5)0.00252 (9)0.0642 (3)
Cl20.61323 (6)0.71900 (6)0.01517 (12)0.0813 (4)
O10.89228 (11)0.72875 (11)0.1540 (3)0.0533 (6)
C40.75598 (14)0.69120 (14)0.1362 (3)0.0379 (6)
C50.68998 (14)0.73415 (15)0.1411 (3)0.0402 (6)
C20.84570 (16)0.62493 (16)0.3155 (3)0.0462 (6)
C30.82653 (13)0.70177 (13)0.2419 (3)0.0363 (6)
C10.8625 (2)0.5634 (2)0.3678 (5)0.0714 (10)
HA0.922 (2)0.696 (2)0.136 (4)0.060 (10)*
H10.876 (3)0.517 (3)0.407 (6)0.112 (17)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0768 (6)0.0581 (5)0.0576 (5)0.0093 (4)0.0049 (4)0.0228 (4)
Cl20.0696 (6)0.0783 (6)0.0961 (8)0.0109 (4)0.0469 (5)0.0194 (5)
O10.0353 (10)0.0313 (9)0.0934 (16)0.0033 (7)0.0256 (10)0.0102 (10)
C40.0398 (13)0.0349 (12)0.0388 (13)0.0001 (9)0.0047 (10)0.0033 (10)
C50.0342 (12)0.0391 (13)0.0473 (14)0.0003 (9)0.0061 (10)0.0012 (10)
C20.0417 (14)0.0389 (14)0.0579 (16)0.0025 (11)0.0049 (12)0.0067 (12)
C30.0272 (11)0.0311 (11)0.0505 (14)0.0012 (9)0.0062 (10)0.0037 (10)
C10.090 (3)0.0497 (19)0.074 (2)0.0115 (18)0.004 (2)0.0184 (17)
Geometric parameters (Å, º) top
Cl1—C41.724 (2)C5—C3i1.518 (3)
Cl2—C51.722 (3)C2—C11.165 (4)
O1—C31.423 (3)C2—C31.479 (3)
O1—HA0.76 (4)C3—C5i1.518 (3)
C4—C51.320 (3)C1—H10.88 (5)
C4—C31.519 (3)
C3—O1—HA113 (3)O1—C3—C2110.49 (19)
C5—C4—C3124.6 (2)O1—C3—C5i106.88 (19)
C5—C4—Cl1122.4 (2)C2—C3—C5i110.7 (2)
C3—C4—Cl1113.00 (17)O1—C3—C4107.6 (2)
C4—C5—C3i124.1 (2)C2—C3—C4109.9 (2)
C4—C5—Cl2121.6 (2)C5i—C3—C4111.22 (18)
C3i—C5—Cl2114.27 (17)C2—C1—H1179 (3)
C1—C2—C3177.0 (3)
Symmetry code: (i) x+3/2, y+3/2, z1/2.
(9) 2,3,5,6-tetrabromo-trans-1,4-diethynyl-cyclohexa-2,5-diene-1,4-diol top
Crystal data top
C10H4Br4O2F(000) = 880
Mr = 475.77Dx = 2.477 Mg m3
Triclinic, P1Melting point = 205–206 K
a = 8.9147 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.6402 (5) ÅCell parameters from 510 reflections
c = 12.6547 (5) Åθ = 5.1–23.7°
α = 85.738 (1)°µ = 12.60 mm1
β = 69.625 (1)°T = 150 K
γ = 72.72 (1)°Block, colourless
V = 1275.76 (8) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
5818 independent reflections
Radiation source: fine-focus sealed tube4966 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: not relevant pixels mm-1θmax = 27.5°, θmin = 1.7°
ω scansh = 1111
Absorption correction: multi-scan
SADABS (Sheldrick 1996)
k = 1616
Tmin = 0.018, Tmax = 0.074l = 1616
14367 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: difference Fourier map
wR(F2) = 0.078All 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 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = 1.05 e Å3
Crystal data top
C10H4Br4O2γ = 72.72 (1)°
Mr = 475.77V = 1275.76 (8) Å3
Triclinic, P1Z = 4
a = 8.9147 (3) ÅMo Kα radiation
b = 12.6402 (5) ŵ = 12.60 mm1
c = 12.6547 (5) ÅT = 150 K
α = 85.738 (1)°0.3 × 0.2 × 0.2 mm
β = 69.625 (1)°
Data collection top
Bruker SMART CCD
diffractometer
5818 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick 1996)
4966 reflections with I > 2σ(I)
Tmin = 0.018, Tmax = 0.074Rint = 0.043
14367 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.078All H-atom parameters refined
S = 1.15Δρmax = 0.80 e Å3
5818 reflectionsΔρmin = 1.05 e Å3
321 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br320.23387 (6)0.17095 (4)0.93445 (4)0.02955 (11)
Br210.26974 (6)0.38542 (4)1.13043 (4)0.02820 (11)
Br220.40392 (6)0.42595 (5)0.85341 (4)0.03255 (12)
Br110.78564 (6)0.43745 (4)0.62350 (4)0.03124 (12)
Br310.40744 (6)0.09732 (4)0.86395 (4)0.02761 (11)
Br10.79084 (7)0.18445 (4)0.59429 (4)0.03404 (12)
Br20.84216 (7)0.08758 (5)0.33470 (4)0.03575 (13)
Br120.48669 (6)0.68322 (4)0.67843 (4)0.02516 (10)
O30.0988 (4)0.3802 (3)1.1712 (3)0.0233 (7)
O11.0803 (5)0.1357 (3)0.6498 (3)0.0273 (7)
C340.1752 (5)0.0377 (3)0.9406 (3)0.0187 (8)
C250.1746 (5)0.4672 (3)0.9417 (4)0.0183 (8)
C40.9092 (5)0.0793 (4)0.5363 (4)0.0218 (9)
C130.6262 (5)0.3856 (3)0.4816 (3)0.0186 (8)
C30.9714 (5)0.0412 (3)0.6199 (3)0.0185 (8)
C50.9306 (6)0.0423 (4)0.4334 (4)0.0215 (9)
C350.1068 (5)0.0694 (3)0.9688 (3)0.0187 (8)
C140.6176 (5)0.4770 (4)0.5572 (3)0.0178 (8)
C150.5043 (5)0.5748 (4)0.5760 (3)0.0183 (8)
C230.0620 (5)0.4806 (3)1.1266 (3)0.0182 (8)
C330.0778 (5)0.1231 (3)0.9671 (3)0.0163 (8)
C240.1214 (5)0.4505 (3)1.0519 (3)0.0187 (8)
O40.0960 (4)0.1677 (3)0.8614 (2)0.0207 (6)
O20.7898 (4)0.3546 (3)0.3984 (3)0.0202 (6)
C220.0946 (5)0.5578 (3)1.2199 (4)0.0201 (8)
C20.8281 (6)0.0123 (4)0.7218 (4)0.0240 (9)
C320.1482 (6)0.2131 (4)1.0344 (4)0.0222 (9)
C210.1280 (6)0.6166 (4)1.2985 (4)0.0268 (10)
C120.5913 (6)0.2906 (4)0.5515 (4)0.0233 (9)
C10.7190 (7)0.0528 (5)0.8056 (4)0.0330 (11)
C110.5609 (7)0.2152 (5)0.6053 (5)0.0385 (13)
C310.2033 (8)0.2869 (5)1.0836 (5)0.0367 (13)
H1A1.056 (8)0.133 (5)0.708 (6)0.038 (19)*
H10.632 (8)0.085 (5)0.867 (6)0.047 (18)*
H4A0.094 (7)0.229 (5)0.869 (5)0.030 (15)*
H110.561 (8)0.153 (5)0.633 (5)0.045 (18)*
H210.158 (8)0.673 (5)1.357 (5)0.045 (17)*
H40.240 (8)0.334 (5)1.109 (5)0.040 (19)*
H3A0.141 (8)0.378 (5)1.225 (5)0.029 (17)*
H2A0.786 (13)0.306 (8)0.390 (8)0.10 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br320.0236 (2)0.0204 (2)0.0428 (3)0.00980 (17)0.0054 (2)0.00317 (19)
Br210.0283 (2)0.0327 (2)0.0253 (2)0.00188 (19)0.01715 (19)0.00119 (18)
Br220.0175 (2)0.0510 (3)0.0243 (2)0.0069 (2)0.00360 (18)0.0001 (2)
Br110.0227 (2)0.0446 (3)0.0255 (2)0.0005 (2)0.01414 (19)0.0070 (2)
Br310.0182 (2)0.0242 (2)0.0356 (3)0.00451 (17)0.00288 (18)0.00867 (18)
Br10.0450 (3)0.0365 (3)0.0266 (2)0.0273 (2)0.0071 (2)0.0038 (2)
Br20.0476 (3)0.0472 (3)0.0276 (2)0.0274 (3)0.0204 (2)0.0041 (2)
Br120.0257 (2)0.0266 (2)0.0248 (2)0.00922 (18)0.00736 (18)0.00823 (17)
O30.0328 (18)0.0211 (16)0.0135 (15)0.0121 (14)0.0015 (14)0.0018 (12)
O10.038 (2)0.0239 (17)0.0175 (17)0.0022 (14)0.0113 (15)0.0002 (13)
C340.017 (2)0.022 (2)0.0153 (19)0.0047 (16)0.0045 (16)0.0016 (15)
C250.0150 (19)0.019 (2)0.020 (2)0.0041 (16)0.0050 (16)0.0008 (16)
C40.020 (2)0.022 (2)0.022 (2)0.0086 (17)0.0025 (17)0.0024 (17)
C130.021 (2)0.020 (2)0.0146 (19)0.0061 (17)0.0056 (16)0.0009 (15)
C30.020 (2)0.018 (2)0.018 (2)0.0048 (16)0.0077 (16)0.0010 (15)
C50.024 (2)0.024 (2)0.019 (2)0.0083 (17)0.0087 (17)0.0006 (16)
C350.022 (2)0.020 (2)0.0161 (19)0.0084 (17)0.0070 (16)0.0005 (15)
C140.0172 (19)0.024 (2)0.0134 (18)0.0065 (16)0.0059 (16)0.0009 (15)
C150.019 (2)0.022 (2)0.0155 (19)0.0088 (16)0.0046 (16)0.0016 (15)
C230.022 (2)0.0175 (19)0.0157 (19)0.0060 (16)0.0082 (17)0.0024 (15)
C330.019 (2)0.0131 (18)0.0165 (19)0.0029 (15)0.0072 (16)0.0026 (15)
C240.019 (2)0.019 (2)0.019 (2)0.0057 (16)0.0076 (17)0.0011 (16)
O40.0311 (17)0.0153 (15)0.0172 (14)0.0073 (13)0.0097 (13)0.0001 (11)
O20.0181 (15)0.0212 (16)0.0173 (15)0.0041 (12)0.0022 (12)0.0014 (12)
C220.021 (2)0.018 (2)0.022 (2)0.0057 (16)0.0088 (17)0.0032 (16)
C20.024 (2)0.029 (2)0.021 (2)0.0078 (18)0.0100 (19)0.0002 (18)
C320.022 (2)0.022 (2)0.023 (2)0.0065 (18)0.0080 (18)0.0002 (17)
C210.029 (2)0.027 (2)0.025 (2)0.0069 (19)0.011 (2)0.0051 (19)
C120.022 (2)0.023 (2)0.021 (2)0.0043 (17)0.0055 (18)0.0027 (17)
C10.026 (3)0.045 (3)0.024 (2)0.007 (2)0.005 (2)0.006 (2)
C110.035 (3)0.033 (3)0.037 (3)0.008 (2)0.004 (2)0.010 (2)
C310.040 (3)0.033 (3)0.043 (3)0.009 (2)0.025 (3)0.015 (2)
Geometric parameters (Å, º) top
Br32—C351.886 (4)C3—C21.491 (6)
Br21—C241.887 (4)C3—C5iii1.537 (6)
Br22—C251.888 (4)C5—C3iii1.537 (6)
Br11—C141.889 (4)C35—C33iv1.522 (6)
Br31—C341.892 (4)C14—C151.319 (6)
Br1—C41.889 (4)C15—C13ii1.525 (6)
Br2—C51.889 (4)C23—C221.481 (6)
Br12—C151.891 (4)C23—C25i1.522 (6)
O3—C231.431 (5)C23—C241.523 (6)
O3—H3A0.66 (6)C33—O41.428 (5)
O1—C31.419 (5)C33—C321.488 (6)
O1—H1A0.69 (6)C33—C35iv1.522 (6)
C34—C351.329 (6)O4—H4A0.78 (6)
C34—C331.526 (6)O2—H2A0.64 (9)
C25—C241.330 (6)C22—C211.185 (6)
C25—C23i1.522 (6)C2—C11.183 (7)
C4—C51.318 (6)C32—C311.164 (7)
C4—C31.517 (6)C21—H210.98 (6)
C13—O21.429 (5)C12—C111.172 (7)
C13—C121.481 (6)C1—H10.90 (7)
C13—C141.522 (6)C11—H110.83 (7)
C13—C15ii1.525 (6)C31—H40.70 (7)
C23—O3—H3A120 (5)C15—C14—Br11122.4 (3)
C3—O1—H1A106 (5)C13—C14—Br11113.5 (3)
C35—C34—C33124.3 (4)C14—C15—C13ii124.6 (4)
C35—C34—Br31121.5 (3)C14—C15—Br12123.3 (3)
C33—C34—Br31114.2 (3)C13ii—C15—Br12112.1 (3)
C24—C25—C23i125.0 (4)O3—C23—C22110.0 (3)
C24—C25—Br22122.0 (3)O3—C23—C25i107.9 (3)
C23i—C25—Br22112.9 (3)C22—C23—C25i109.8 (3)
C5—C4—C3124.5 (4)O3—C23—C24107.7 (3)
C5—C4—Br1122.0 (3)C22—C23—C24110.6 (4)
C3—C4—Br1113.5 (3)C25i—C23—C24110.8 (3)
O2—C13—C12111.3 (4)O4—C33—C32109.9 (3)
O2—C13—C14107.8 (3)O4—C33—C35iv109.2 (3)
C12—C13—C14109.0 (3)C32—C33—C35iv109.8 (3)
O2—C13—C15ii109.7 (3)O4—C33—C34106.7 (3)
C12—C13—C15ii108.0 (4)C32—C33—C34110.1 (3)
C14—C13—C15ii111.1 (3)C35iv—C33—C34111.1 (3)
O1—C3—C2110.5 (4)C25—C24—C23124.1 (4)
O1—C3—C4107.8 (3)C25—C24—Br21122.3 (3)
C2—C3—C4110.4 (4)C23—C24—Br21113.5 (3)
O1—C3—C5iii108.6 (4)C33—O4—H4A108 (4)
C2—C3—C5iii108.8 (3)C13—O2—H2A93 (9)
C4—C3—C5iii110.8 (3)C21—C22—C23176.0 (5)
C4—C5—C3iii124.7 (4)C1—C2—C3176.9 (5)
C4—C5—Br2122.9 (3)C31—C32—C33176.9 (5)
C3iii—C5—Br2112.5 (3)C22—C21—H21173 (4)
C34—C35—C33iv124.7 (4)C11—C12—C13178.2 (6)
C34—C35—Br32122.3 (3)C2—C1—H1177 (4)
C33iv—C35—Br32113.0 (3)C12—C11—H11167 (5)
C15—C14—C13124.1 (4)C32—C31—H4175 (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 formulaC10H4F4O2C10H4Cl4O2C10H4Br4O2
Mr232.13297.93475.77
Crystal system, space groupTriclinic, P1Tetragonal, I41/aTriclinic, P1
Temperature (K)150150150
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, 9085.738 (1), 69.625 (1), 72.72 (1)
V3)708.3 (2)2489.6 (7)1275.76 (8)
Z384
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.170.9312.60
Crystal size (mm)0.7 × 0.3 × 0.20.3 × 0.3 × 0.20.3 × 0.2 × 0.2
Data collection
DiffractometerBruker SMART CCD
diffractometer
Bruker SMART CCD
diffractometer
Bruker SMART CCD
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)
Multi-scan
SADABS (Sheldrick 1996)
Multi-scan
SADABS (Sheldrick 1996)
Tmin, Tmax0.289, 0.3820.665, 0.8300.018, 0.074
No. of measured, independent and
observed [I > 2σ(I)] reflections
8674, 3722, 3376 8404, 1421, 1202 14367, 5818, 4966
Rint0.0290.0430.043
(sin θ/λ)max1)0.7010.6470.649
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 reflections372214215818
No. of parameters24282321
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.46, 0.240.59, 0.440.80, 1.05

Computer programs: Bruker SMART (Bruker Systems Inc., 1999a), Bruker SAINT (Bruker Systems Inc., 1999b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

 

Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds