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The sterically encumbered terphenyl halides 2'-chloro-2,2'',4,4'',6,6''-hexaisopropyl-1,1':3',1''-terphenyl, C36H49Cl, (I), 2'-bromo-2,2'',4,4'',6,6''-hexaisopropyl-1,1':3',1''-terphenyl, C36H49Br, (II), and 2'-iodo-2,2'',4,4'',6,6''-hexaisopropyl-1,1':3',1''-terphenyl, C36H49I, (III), crystallize in space group Pnma. They are isomorphous and isostructural with a plane of symmetry through the centre of the molecule. The C-halide bond distances are 1.745 (3), 1.910 (4) and 2.102 (6) Å for (I)-(III), respectively.
Supporting information
CCDC references: 153942; 153943; 153944
Data collection: SMART (Bruker, 1998) for (I), (II); P3 (Siemens, 1991) for (III). Cell refinement: SMART for (I), (II); P3 for (III). Data reduction: SHELXTL (Sheldrick, 1998) for (I), (II); XDISK (Siemens, 1991) for (III). For all compounds, program(s) used to solve structure: XS in SHELXTL; program(s) used to refine structure: XL in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.
Crystal data top
C36H49Cl | Dx = 1.049 Mg m−3 |
Mr = 517.20 | Melting point = 183–185 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 4302 reflections |
a = 8.2186 (5) Å | θ = 2.6–31.4° |
b = 25.4368 (16) Å | µ = 0.14 mm−1 |
c = 15.6604 (10) Å | T = 93 K |
V = 3273.9 (4) Å3 | Needle, colourless |
Z = 4 | 0.32 × 0.15 × 0.04 mm |
F(000) = 1128 | |
Data collection top
Bruker SMART 1000 diffractometer | 3852 independent reflections |
Radiation source: normal-focus sealed tube | 2275 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.134 |
ω scans | θmax = 27.5°, θmin = 1.5° |
Absorption correction: empirical (SADABS; Sheldrick 1999) | h = 0→10 |
Tmin = 0.957, Tmax = 0.995 | k = 0→33 |
47039 measured reflections | l = 0→20 |
Refinement top
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3 |
3852 reflections | (Δ/σ)max = 0.001 |
172 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl | 0.76901 (9) | 0.7500 | 0.08567 (5) | 0.0309 (2) | |
C1 | 0.9191 (3) | 0.7500 | 0.00683 (16) | 0.0187 (6) | |
C2 | 0.9761 (2) | 0.70181 (7) | −0.02378 (11) | 0.0166 (4) | |
C3 | 1.0940 (2) | 0.70293 (7) | −0.08762 (12) | 0.0203 (4) | |
H3A | 1.1348 | 0.6708 | −0.1098 | 0.024* | |
C4 | 1.1530 (3) | 0.7500 | −0.11946 (18) | 0.0243 (6) | |
H4A | 1.2336 | 0.7500 | −0.1629 | 0.029* | |
C5 | 0.9115 (2) | 0.65045 (7) | 0.00889 (12) | 0.0175 (4) | |
C6 | 0.9854 (2) | 0.62594 (7) | 0.07899 (12) | 0.0199 (4) | |
C7 | 0.9225 (2) | 0.57777 (7) | 0.10680 (12) | 0.0229 (4) | |
H7A | 0.9707 | 0.5611 | 0.1548 | 0.028* | |
C8 | 0.7921 (2) | 0.55355 (7) | 0.06661 (12) | 0.0198 (4) | |
C9 | 0.7221 (2) | 0.57888 (7) | −0.00278 (12) | 0.0207 (4) | |
H9A | 0.6328 | 0.5627 | −0.0309 | 0.025* | |
C10 | 0.7782 (2) | 0.62706 (7) | −0.03249 (12) | 0.0187 (4) | |
C11 | 1.1353 (2) | 0.64923 (8) | 0.12216 (13) | 0.0251 (5) | |
H11A | 1.1594 | 0.6836 | 0.0937 | 0.030* | |
C12 | 1.1081 (3) | 0.66018 (10) | 0.21677 (14) | 0.0377 (6) | |
H12A | 1.0137 | 0.6833 | 0.2237 | 0.057* | |
H12B | 1.2048 | 0.6773 | 0.2407 | 0.057* | |
H12C | 1.0883 | 0.6270 | 0.2468 | 0.057* | |
C13 | 1.2824 (2) | 0.61354 (10) | 0.10894 (14) | 0.0367 (6) | |
H13A | 1.2977 | 0.6071 | 0.0478 | 0.055* | |
H13B | 1.2642 | 0.5800 | 0.1383 | 0.055* | |
H13C | 1.3797 | 0.6305 | 0.1323 | 0.055* | |
C14 | 0.7274 (2) | 0.50057 (7) | 0.09675 (12) | 0.0225 (4) | |
H14A | 0.6518 | 0.4873 | 0.0516 | 0.027* | |
C15 | 0.6292 (3) | 0.50614 (8) | 0.17857 (14) | 0.0336 (5) | |
H15A | 0.5430 | 0.5322 | 0.1701 | 0.050* | |
H15B | 0.7009 | 0.5176 | 0.2250 | 0.050* | |
H15C | 0.5804 | 0.4722 | 0.1933 | 0.050* | |
C16 | 0.8623 (3) | 0.45979 (8) | 0.10701 (14) | 0.0286 (5) | |
H16A | 0.9231 | 0.4568 | 0.0534 | 0.043* | |
H16B | 0.8143 | 0.4257 | 0.1214 | 0.043* | |
H16C | 0.9362 | 0.4708 | 0.1528 | 0.043* | |
C17 | 0.6986 (2) | 0.65265 (8) | −0.10990 (13) | 0.0236 (4) | |
H17A | 0.7451 | 0.6888 | −0.1157 | 0.028* | |
C18 | 0.5146 (3) | 0.65828 (9) | −0.10040 (14) | 0.0362 (6) | |
H18A | 0.4900 | 0.6780 | −0.0482 | 0.054* | |
H18B | 0.4648 | 0.6233 | −0.0970 | 0.054* | |
H18C | 0.4707 | 0.6771 | −0.1499 | 0.054* | |
C19 | 0.7407 (3) | 0.62236 (9) | −0.19121 (13) | 0.0355 (5) | |
H19A | 0.8591 | 0.6192 | −0.1963 | 0.053* | |
H19B | 0.6977 | 0.6412 | −0.2409 | 0.053* | |
H19D | 0.6922 | 0.5872 | −0.1886 | 0.053* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0331 (4) | 0.0259 (4) | 0.0336 (4) | 0.000 | 0.0144 (3) | 0.000 |
C1 | 0.0173 (13) | 0.0224 (14) | 0.0165 (13) | 0.000 | 0.0020 (10) | 0.000 |
C2 | 0.0170 (9) | 0.0155 (9) | 0.0174 (9) | −0.0005 (7) | −0.0034 (7) | 0.0012 (7) |
C3 | 0.0223 (10) | 0.0150 (9) | 0.0235 (10) | 0.0027 (8) | 0.0031 (8) | −0.0033 (8) |
C4 | 0.0216 (14) | 0.0257 (15) | 0.0256 (15) | 0.000 | 0.0077 (12) | 0.000 |
C5 | 0.0171 (9) | 0.0149 (9) | 0.0204 (10) | 0.0012 (7) | 0.0033 (7) | 0.0007 (8) |
C6 | 0.0212 (10) | 0.0188 (9) | 0.0197 (10) | 0.0009 (8) | −0.0011 (8) | 0.0002 (8) |
C7 | 0.0257 (10) | 0.0218 (10) | 0.0212 (10) | 0.0032 (8) | 0.0000 (8) | 0.0039 (8) |
C8 | 0.0211 (10) | 0.0156 (9) | 0.0227 (10) | 0.0000 (8) | 0.0041 (8) | 0.0014 (8) |
C9 | 0.0184 (9) | 0.0196 (10) | 0.0242 (10) | −0.0021 (8) | −0.0001 (8) | −0.0022 (8) |
C10 | 0.0192 (9) | 0.0167 (9) | 0.0201 (9) | 0.0012 (8) | 0.0012 (8) | −0.0019 (8) |
C11 | 0.0261 (11) | 0.0255 (11) | 0.0238 (11) | −0.0066 (9) | −0.0061 (8) | 0.0048 (9) |
C12 | 0.0281 (12) | 0.0509 (15) | 0.0341 (13) | −0.0042 (11) | −0.0044 (10) | −0.0133 (11) |
C13 | 0.0229 (11) | 0.0532 (15) | 0.0339 (13) | −0.0033 (10) | −0.0025 (9) | −0.0031 (11) |
C14 | 0.0236 (10) | 0.0182 (9) | 0.0259 (11) | −0.0029 (8) | 0.0016 (8) | 0.0016 (8) |
C15 | 0.0361 (13) | 0.0225 (11) | 0.0422 (13) | 0.0009 (9) | 0.0166 (10) | 0.0055 (10) |
C16 | 0.0333 (12) | 0.0187 (10) | 0.0338 (12) | 0.0001 (9) | 0.0053 (10) | 0.0019 (9) |
C17 | 0.0234 (10) | 0.0199 (9) | 0.0275 (11) | −0.0037 (8) | −0.0052 (8) | 0.0046 (9) |
C18 | 0.0287 (12) | 0.0444 (14) | 0.0355 (13) | 0.0073 (10) | −0.0067 (10) | 0.0051 (11) |
C19 | 0.0404 (13) | 0.0442 (13) | 0.0219 (11) | 0.0035 (11) | −0.0009 (10) | 0.0046 (10) |
Geometric parameters (Å, º) top
Cl—C1 | 1.745 (3) | C7—C8 | 1.387 (3) |
C1—C2i | 1.397 (2) | C8—C9 | 1.388 (3) |
C1—C2 | 1.397 (2) | C8—C14 | 1.524 (2) |
C2—C3 | 1.392 (3) | C9—C10 | 1.390 (3) |
C2—C5 | 1.500 (3) | C10—C17 | 1.524 (3) |
C3—C4 | 1.385 (2) | C11—C12 | 1.524 (3) |
C4—C3i | 1.385 (2) | C11—C13 | 1.526 (3) |
C5—C6 | 1.401 (3) | C14—C15 | 1.521 (3) |
C5—C10 | 1.405 (2) | C14—C16 | 1.527 (3) |
C6—C7 | 1.399 (3) | C17—C18 | 1.526 (3) |
C6—C11 | 1.525 (3) | C17—C19 | 1.528 (3) |
| | | |
C2i—C1—C2 | 122.6 (2) | C7—C8—C14 | 121.44 (17) |
C2i—C1—Cl | 118.68 (12) | C9—C8—C14 | 120.58 (17) |
C2—C1—Cl | 118.68 (12) | C8—C9—C10 | 122.29 (18) |
C3—C2—C1 | 117.51 (17) | C9—C10—C5 | 118.53 (17) |
C3—C2—C5 | 120.60 (16) | C9—C10—C17 | 120.04 (17) |
C1—C2—C5 | 121.87 (17) | C5—C10—C17 | 121.40 (16) |
C4—C3—C2 | 121.33 (18) | C12—C11—C6 | 112.55 (17) |
C3i—C4—C3 | 119.7 (3) | C12—C11—C13 | 110.91 (17) |
C6—C5—C10 | 120.73 (17) | C6—C11—C13 | 110.40 (17) |
C6—C5—C2 | 120.07 (16) | C15—C14—C8 | 111.33 (16) |
C10—C5—C2 | 119.19 (16) | C15—C14—C16 | 111.10 (16) |
C7—C6—C5 | 118.25 (17) | C8—C14—C16 | 112.36 (16) |
C7—C6—C11 | 120.05 (17) | C10—C17—C18 | 112.84 (17) |
C5—C6—C11 | 121.65 (16) | C10—C17—C19 | 110.52 (16) |
C8—C7—C6 | 122.21 (18) | C18—C17—C19 | 110.66 (17) |
C7—C8—C9 | 117.98 (17) | | |
Symmetry code: (i) x, −y+3/2, z. |
Crystal data top
C36H49Br | Dx = 1.100 Mg m−3 |
Mr = 561.66 | Melting point = 211–213 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 934 reflections |
a = 8.2823 (14) Å | θ = 2.9–24.6° |
b = 25.831 (4) Å | µ = 1.23 mm−1 |
c = 15.856 (3) Å | T = 293 K |
V = 3392.2 (10) Å3 | Needle, colourless |
Z = 4 | 0.78 × 0.30 × 0.20 mm |
F(000) = 1200 | |
Data collection top
Siemens SMART 1000 diffractometer | 3054 independent reflections |
Radiation source: normal-focus sealed tube | 2418 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1999) | h = −9→9 |
Tmin = 0.447, Tmax = 0.791 | k = −25→30 |
23472 measured reflections | l = −18→18 |
Refinement top
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0522P)2 + 2.2426P] where P = (Fo2 + 2Fc2)/3 |
3054 reflections | (Δ/σ)max < 0.001 |
178 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.24164 (5) | 0.2500 | 0.08168 (3) | 0.06490 (18) | |
C1 | 0.0743 (4) | 0.2500 | −0.0012 (2) | 0.0414 (8) | |
C2 | 0.0161 (3) | 0.20251 (9) | −0.02953 (15) | 0.0418 (5) | |
C3 | −0.1037 (3) | 0.20376 (10) | −0.09109 (17) | 0.0508 (6) | |
H3A | −0.1454 | 0.1728 | −0.1117 | 0.061* | |
C4 | −0.1617 (5) | 0.2500 | −0.1220 (3) | 0.0594 (10) | |
H4A | −0.2402 | 0.2500 | −0.1639 | 0.071* | |
C5 | 0.0775 (3) | 0.15204 (9) | 0.00404 (16) | 0.0453 (6) | |
C10 | 0.2068 (3) | 0.12733 (10) | −0.03584 (19) | 0.0528 (7) | |
C9 | 0.2638 (4) | 0.08101 (11) | −0.0030 (2) | 0.0665 (8) | |
H9A | 0.3499 | 0.0647 | −0.0296 | 0.080* | |
C8 | 0.1980 (4) | 0.05838 (12) | 0.0674 (2) | 0.0697 (9) | |
C7 | 0.0710 (4) | 0.08338 (12) | 0.1060 (2) | 0.0725 (9) | |
H7A | 0.0259 | 0.0687 | 0.1540 | 0.087* | |
C6 | 0.0065 (3) | 0.13033 (11) | 0.07565 (17) | 0.0560 (7) | |
C11 | 0.2841 (4) | 0.14968 (13) | −0.1152 (2) | 0.0703 (9) | |
H11A | 0.2336 | 0.1833 | −0.1260 | 0.084* | |
C12 | 0.4644 (5) | 0.15880 (19) | −0.1050 (3) | 0.1154 (16) | |
H12A | 0.4831 | 0.1806 | −0.0569 | 0.173* | |
H12B | 0.5059 | 0.1754 | −0.1547 | 0.173* | |
H12C | 0.5181 | 0.1262 | −0.0970 | 0.173* | |
C13 | 0.2518 (5) | 0.1156 (2) | −0.1914 (3) | 0.1123 (15) | |
H13A | 0.1374 | 0.1113 | −0.1984 | 0.168* | |
H13B | 0.3013 | 0.0824 | −0.1831 | 0.168* | |
H13C | 0.2962 | 0.1316 | −0.2409 | 0.168* | |
C14 | 0.2622 (5) | 0.00737 (14) | 0.1019 (3) | 0.1032 (15) | |
H14A | 0.3353 | −0.0025 | 0.0560 | 0.124* | |
C15 | 0.1514 (7) | −0.03449 (14) | 0.0987 (3) | 0.131 (2) | |
H15A | 0.2035 | −0.0655 | 0.1180 | 0.196* | |
H15B | 0.1154 | −0.0393 | 0.0416 | 0.196* | |
H15C | 0.0604 | −0.0270 | 0.1341 | 0.196* | |
C16 | 0.3750 (6) | 0.01304 (15) | 0.1686 (3) | 0.135 (2) | |
H16A | 0.4559 | 0.0378 | 0.1528 | 0.203* | |
H16B | 0.4252 | −0.0197 | 0.1799 | 0.203* | |
H16C | 0.3200 | 0.0249 | 0.2183 | 0.203* | |
C17 | −0.1374 (4) | 0.15552 (14) | 0.1187 (2) | 0.0784 (10) | |
H17A | −0.1577 | 0.1886 | 0.0904 | 0.094* | |
C18 | −0.2889 (5) | 0.1220 (2) | 0.1082 (3) | 0.1263 (19) | |
H18A | −0.3812 | 0.1404 | 0.1290 | 0.190* | |
H18B | −0.2761 | 0.0904 | 0.1394 | 0.190* | |
H18C | −0.3042 | 0.1140 | 0.0496 | 0.190* | |
C19 | −0.1076 (6) | 0.16682 (18) | 0.2114 (3) | 0.1134 (15) | |
H19A | −0.1967 | 0.1862 | 0.2338 | 0.170* | |
H19B | −0.0101 | 0.1866 | 0.2173 | 0.170* | |
H19C | −0.0971 | 0.1348 | 0.2416 | 0.170* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0728 (3) | 0.0520 (3) | 0.0700 (3) | 0.000 | −0.0348 (2) | 0.000 |
C1 | 0.0409 (18) | 0.0421 (19) | 0.0411 (18) | 0.000 | −0.0078 (14) | 0.000 |
C2 | 0.0437 (13) | 0.0367 (13) | 0.0451 (14) | −0.0009 (10) | −0.0014 (11) | 0.0004 (10) |
C3 | 0.0532 (15) | 0.0403 (14) | 0.0589 (16) | −0.0065 (11) | −0.0105 (12) | −0.0046 (12) |
C4 | 0.056 (2) | 0.059 (3) | 0.063 (3) | 0.000 | −0.023 (2) | 0.000 |
C5 | 0.0502 (14) | 0.0347 (12) | 0.0510 (15) | −0.0043 (11) | −0.0090 (12) | 0.0012 (11) |
C10 | 0.0539 (15) | 0.0396 (14) | 0.0649 (18) | −0.0002 (12) | −0.0046 (13) | 0.0001 (13) |
C9 | 0.0652 (19) | 0.0459 (16) | 0.088 (2) | 0.0075 (14) | −0.0118 (16) | 0.0013 (15) |
C8 | 0.073 (2) | 0.0464 (17) | 0.090 (2) | 0.0009 (15) | −0.0246 (18) | 0.0092 (16) |
C7 | 0.091 (2) | 0.0619 (19) | 0.0650 (19) | −0.0180 (18) | −0.0105 (17) | 0.0249 (16) |
C6 | 0.0627 (17) | 0.0482 (15) | 0.0571 (16) | −0.0042 (13) | −0.0030 (13) | 0.0079 (13) |
C11 | 0.0674 (19) | 0.0614 (19) | 0.082 (2) | 0.0137 (15) | 0.0161 (17) | 0.0087 (17) |
C12 | 0.081 (3) | 0.141 (4) | 0.125 (4) | −0.030 (3) | 0.022 (3) | −0.007 (3) |
C13 | 0.116 (4) | 0.149 (4) | 0.072 (3) | −0.019 (3) | 0.006 (2) | −0.004 (3) |
C14 | 0.121 (3) | 0.0505 (19) | 0.138 (4) | −0.006 (2) | −0.057 (3) | 0.031 (2) |
C15 | 0.164 (4) | 0.050 (2) | 0.179 (5) | −0.008 (3) | −0.087 (4) | 0.017 (3) |
C16 | 0.158 (4) | 0.069 (3) | 0.179 (5) | −0.004 (3) | −0.099 (4) | 0.027 (3) |
C17 | 0.084 (2) | 0.089 (2) | 0.062 (2) | 0.0058 (19) | 0.0160 (17) | 0.0201 (18) |
C18 | 0.077 (3) | 0.195 (6) | 0.107 (3) | −0.009 (3) | 0.008 (2) | −0.026 (4) |
C19 | 0.118 (3) | 0.134 (4) | 0.089 (3) | −0.009 (3) | 0.016 (3) | −0.023 (3) |
Geometric parameters (Å, º) top
Br1—C1 | 1.910 (3) | C9—C8 | 1.372 (5) |
C1—C2i | 1.393 (3) | C8—C7 | 1.378 (5) |
C1—C2 | 1.393 (3) | C8—C14 | 1.523 (4) |
C2—C3 | 1.392 (3) | C7—C6 | 1.410 (4) |
C2—C5 | 1.497 (3) | C6—C17 | 1.519 (4) |
C3—C4 | 1.378 (3) | C11—C13 | 1.518 (6) |
C4—C3i | 1.378 (3) | C11—C12 | 1.520 (5) |
C5—C6 | 1.396 (4) | C14—C16 | 1.419 (5) |
C5—C10 | 1.398 (4) | C14—C15 | 1.419 (6) |
C10—C9 | 1.388 (4) | C17—C19 | 1.519 (5) |
C10—C11 | 1.526 (5) | C17—C18 | 1.535 (6) |
| | | |
C2i—C1—C2 | 123.5 (3) | C9—C8—C14 | 121.5 (4) |
C2i—C1—Br1 | 118.25 (15) | C7—C8—C14 | 120.8 (4) |
C2—C1—Br1 | 118.25 (15) | C8—C7—C6 | 122.8 (3) |
C3—C2—C1 | 116.9 (2) | C5—C6—C7 | 117.6 (3) |
C3—C2—C5 | 120.8 (2) | C5—C6—C17 | 121.6 (3) |
C1—C2—C5 | 122.3 (2) | C7—C6—C17 | 120.9 (3) |
C4—C3—C2 | 121.2 (2) | C13—C11—C12 | 110.3 (3) |
C3—C4—C3i | 120.2 (3) | C13—C11—C10 | 111.3 (3) |
C6—C5—C10 | 120.5 (2) | C12—C11—C10 | 112.5 (3) |
C6—C5—C2 | 119.7 (2) | C16—C14—C15 | 122.1 (4) |
C10—C5—C2 | 119.8 (2) | C16—C14—C8 | 114.1 (3) |
C9—C10—C5 | 119.0 (3) | C15—C14—C8 | 114.9 (3) |
C9—C10—C11 | 119.6 (3) | C19—C17—C6 | 112.9 (3) |
C5—C10—C11 | 121.5 (2) | C19—C17—C18 | 110.3 (3) |
C8—C9—C10 | 122.5 (3) | C6—C17—C18 | 110.5 (3) |
C9—C8—C7 | 117.7 (3) | | |
Symmetry code: (i) x, −y+1/2, z. |
Crystal data top
C36H49I | Dx = 1.221 Mg m−3 |
Mr = 608.65 | Melting point = 229–230 K |
Orthorhombic, Pnma | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2n | Cell parameters from 50 reflections |
a = 8.1100 (13) Å | θ = 4.7–14.7° |
b = 25.549 (6) Å | µ = 0.99 mm−1 |
c = 15.978 (6) Å | T = 130 K |
V = 3310.7 (16) Å3 | Parallelepiped, colourless |
Z = 4 | 0.76 × 0.36 × 0.30 mm |
F(000) = 1272 | |
Data collection top
Siemens R3 diffractometer | 3185 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 27.5°, θmin = 1.5° |
ω scans | h = 0→10 |
Absorption correction: empirical (XABS2; Parkin et al., 1995) | k = 0→33 |
Tmin = 0.521, Tmax = 0.756 | l = 0→20 |
8539 measured reflections | 2 standard reflections every 198 reflections |
3891 independent reflections | intensity decay: 1% |
Refinement top
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.186 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.111P)2 + 10.4168P] where P = (Fo2 + 2Fc2)/3 |
3891 reflections | (Δ/σ)max < 0.001 |
172 parameters | Δρmax = 0.97 e Å−3 |
0 restraints | Δρmin = −0.94 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
I1 | 1.22084 (6) | 0.2500 | 0.41305 (3) | 0.02783 (19) | |
C1 | 1.4154 (6) | 0.2500 | 0.4997 (3) | 0.0087 (9) | |
C2 | 1.4756 (5) | 0.20210 (14) | 0.5294 (2) | 0.0073 (7) | |
C3 | 1.5976 (5) | 0.20280 (15) | 0.5910 (2) | 0.0122 (7) | |
H3A | 1.6401 | 0.1707 | 0.6118 | 0.015* | |
C4 | 1.6581 (8) | 0.2500 | 0.6225 (4) | 0.0153 (11) | |
H4A | 1.7398 | 0.2500 | 0.6651 | 0.018* | |
C5 | 1.4130 (4) | 0.15090 (13) | 0.4969 (2) | 0.0077 (7) | |
C10 | 1.2802 (5) | 0.12595 (15) | 0.5370 (2) | 0.0098 (7) | |
C9 | 1.2222 (5) | 0.07846 (16) | 0.5059 (2) | 0.0124 (7) | |
H9A | 1.1326 | 0.0617 | 0.5332 | 0.015* | |
C8 | 1.2917 (5) | 0.05509 (15) | 0.4361 (3) | 0.0128 (7) | |
C7 | 1.4233 (5) | 0.08049 (15) | 0.3964 (2) | 0.0129 (7) | |
H7A | 1.4710 | 0.0651 | 0.3480 | 0.016* | |
C6 | 1.4863 (5) | 0.12782 (15) | 0.4260 (2) | 0.0113 (7) | |
C11 | 1.6357 (5) | 0.15249 (17) | 0.3838 (3) | 0.0175 (8) | |
H11A | 1.6593 | 0.1866 | 0.4121 | 0.021* | |
C12 | 1.6046 (7) | 0.1634 (2) | 0.2913 (3) | 0.0331 (12) | |
H12A | 1.5077 | 0.1860 | 0.2854 | 0.050* | |
H12B | 1.5850 | 0.1302 | 0.2620 | 0.050* | |
H12C | 1.7011 | 0.1808 | 0.2671 | 0.050* | |
C13 | 1.7865 (6) | 0.1171 (3) | 0.3942 (3) | 0.0311 (12) | |
H13A | 1.8051 | 0.1103 | 0.4539 | 0.047* | |
H13B | 1.8837 | 0.1344 | 0.3705 | 0.047* | |
H13C | 1.7675 | 0.0839 | 0.3651 | 0.047* | |
C14 | 1.2256 (5) | 0.00332 (17) | 0.4027 (3) | 0.0160 (8) | |
H14A | 1.1451 | −0.0102 | 0.4449 | 0.019* | |
C15 | 1.1324 (7) | 0.01049 (19) | 0.3213 (3) | 0.0293 (11) | |
H15A | 1.0917 | −0.0235 | 0.3018 | 0.044* | |
H15B | 1.2062 | 0.0255 | 0.2791 | 0.044* | |
H15C | 1.0389 | 0.0341 | 0.3304 | 0.044* | |
C16 | 1.3613 (6) | −0.03780 (16) | 0.3938 (3) | 0.0220 (9) | |
H16A | 1.3137 | −0.0704 | 0.3723 | 0.033* | |
H16B | 1.4116 | −0.0443 | 0.4486 | 0.033* | |
H16C | 1.4456 | −0.0251 | 0.3548 | 0.033* | |
C17 | 1.2017 (5) | 0.14941 (16) | 0.6154 (3) | 0.0149 (8) | |
H17A | 1.2479 | 0.1854 | 0.6232 | 0.018* | |
C19 | 1.0140 (6) | 0.1543 (2) | 0.6081 (3) | 0.0277 (11) | |
H19A | 0.9696 | 0.1694 | 0.6597 | 0.042* | |
H19B | 0.9659 | 0.1195 | 0.5992 | 0.042* | |
H19C | 0.9866 | 0.1770 | 0.5607 | 0.042* | |
C18 | 1.2465 (7) | 0.1173 (2) | 0.6920 (3) | 0.0294 (11) | |
H18A | 1.3668 | 0.1144 | 0.6960 | 0.044* | |
H18B | 1.1980 | 0.0823 | 0.6872 | 0.044* | |
H18C | 1.2038 | 0.1346 | 0.7423 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
I1 | 0.0289 (3) | 0.0264 (3) | 0.0282 (3) | 0.000 | −0.01479 (18) | 0.000 |
C1 | 0.005 (2) | 0.010 (2) | 0.011 (2) | 0.000 | −0.0019 (18) | 0.000 |
C2 | 0.0042 (16) | 0.0099 (15) | 0.0079 (15) | 0.0017 (13) | 0.0018 (12) | −0.0005 (12) |
C3 | 0.0092 (18) | 0.0120 (16) | 0.0153 (18) | 0.0019 (14) | −0.0040 (14) | 0.0013 (13) |
C4 | 0.016 (3) | 0.015 (2) | 0.015 (3) | 0.000 | −0.009 (2) | 0.000 |
C5 | 0.0055 (16) | 0.0088 (15) | 0.0087 (16) | −0.0004 (13) | −0.0024 (13) | 0.0005 (12) |
C10 | 0.0040 (16) | 0.0139 (16) | 0.0114 (17) | 0.0019 (14) | 0.0010 (13) | −0.0001 (13) |
C9 | 0.0077 (17) | 0.0155 (17) | 0.0140 (17) | −0.0015 (15) | 0.0012 (14) | 0.0009 (14) |
C8 | 0.0097 (18) | 0.0123 (16) | 0.0164 (18) | −0.0022 (14) | −0.0039 (15) | −0.0007 (14) |
C7 | 0.0135 (19) | 0.0157 (17) | 0.0096 (16) | −0.0015 (15) | 0.0026 (14) | −0.0040 (14) |
C6 | 0.0080 (18) | 0.0135 (17) | 0.0123 (17) | −0.0022 (14) | 0.0047 (13) | −0.0005 (13) |
C11 | 0.016 (2) | 0.0228 (19) | 0.0137 (18) | −0.0067 (16) | 0.0105 (16) | −0.0025 (16) |
C12 | 0.023 (2) | 0.051 (3) | 0.026 (2) | −0.002 (2) | 0.008 (2) | 0.019 (2) |
C13 | 0.011 (2) | 0.056 (3) | 0.026 (2) | −0.002 (2) | 0.0017 (18) | 0.006 (2) |
C14 | 0.017 (2) | 0.0142 (18) | 0.0165 (19) | −0.0050 (16) | −0.0014 (16) | −0.0036 (14) |
C15 | 0.027 (3) | 0.022 (2) | 0.039 (3) | 0.0011 (19) | −0.022 (2) | −0.006 (2) |
C16 | 0.024 (2) | 0.0136 (18) | 0.028 (2) | 0.0012 (17) | −0.0101 (19) | −0.0025 (16) |
C17 | 0.0110 (19) | 0.0192 (18) | 0.0145 (18) | 0.0003 (15) | 0.0079 (15) | −0.0037 (15) |
C19 | 0.013 (2) | 0.050 (3) | 0.021 (2) | 0.010 (2) | 0.0046 (17) | 0.000 (2) |
C18 | 0.029 (3) | 0.048 (3) | 0.012 (2) | 0.007 (2) | 0.0010 (18) | −0.003 (2) |
Geometric parameters (Å, º) top
I1—C1 | 2.099 (5) | C9—C8 | 1.385 (6) |
C1—C2i | 1.401 (4) | C8—C7 | 1.401 (6) |
C1—C2 | 1.401 (4) | C8—C14 | 1.523 (5) |
C2—C3 | 1.395 (5) | C7—C6 | 1.395 (5) |
C2—C5 | 1.496 (5) | C6—C11 | 1.523 (5) |
C3—C4 | 1.396 (5) | C11—C12 | 1.524 (6) |
C4—C3i | 1.396 (5) | C11—C13 | 1.530 (7) |
C5—C10 | 1.407 (5) | C14—C15 | 1.516 (6) |
C5—C6 | 1.409 (5) | C14—C16 | 1.528 (6) |
C10—C9 | 1.393 (5) | C17—C18 | 1.517 (7) |
C10—C17 | 1.527 (5) | C17—C19 | 1.532 (6) |
| | | |
C2i—C1—C2 | 121.8 (5) | C9—C8—C14 | 120.8 (4) |
C2i—C1—I1 | 119.1 (2) | C7—C8—C14 | 120.8 (4) |
C2—C1—I1 | 119.1 (2) | C6—C7—C8 | 121.8 (4) |
C3—C2—C1 | 118.4 (4) | C7—C6—C5 | 118.8 (3) |
C3—C2—C5 | 119.8 (3) | C7—C6—C11 | 120.0 (3) |
C1—C2—C5 | 121.8 (3) | C5—C6—C11 | 121.2 (3) |
C2—C3—C4 | 121.0 (4) | C6—C11—C12 | 111.9 (4) |
C3—C4—C3i | 119.5 (5) | C6—C11—C13 | 110.1 (4) |
C10—C5—C6 | 120.0 (3) | C12—C11—C13 | 110.2 (4) |
C10—C5—C2 | 119.9 (3) | C15—C14—C8 | 111.8 (4) |
C6—C5—C2 | 120.1 (3) | C15—C14—C16 | 111.2 (4) |
C9—C10—C5 | 119.4 (3) | C8—C14—C16 | 112.1 (3) |
C9—C10—C17 | 119.6 (3) | C18—C17—C10 | 110.5 (4) |
C5—C10—C17 | 121.0 (3) | C18—C17—C19 | 110.1 (4) |
C8—C9—C10 | 121.7 (4) | C10—C17—C19 | 112.5 (4) |
C9—C8—C7 | 118.4 (4) | | |
Symmetry code: (i) x, −y+1/2, z. |
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