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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013020/qa0383sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013020/qa0383Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013020/qa0383IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013020/qa0383IIIsup4.hkl
Contains datablock III

CCDC references: 153942; 153943; 153944

Computing details top

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.

(I) top
Crystal data top
C36H49ClDx = 1.049 Mg m3
Mr = 517.20Melting point = 183–185 K
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 4302 reflections
a = 8.2186 (5) Åθ = 2.6–31.4°
b = 25.4368 (16) ŵ = 0.14 mm1
c = 15.6604 (10) ÅT = 93 K
V = 3273.9 (4) Å3Needle, colourless
Z = 40.32 × 0.15 × 0.04 mm
F(000) = 1128
Data collection top
Bruker SMART 1000
diffractometer
3852 independent reflections
Radiation source: normal-focus sealed tube2275 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.134
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: empirical
(SADABS; Sheldrick 1999)
h = 010
Tmin = 0.957, Tmax = 0.995k = 033
47039 measured reflectionsl = 020
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-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 parametersΔρmax = 0.55 e Å3
0 restraintsΔρmin = 0.42 e Å3
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
Cl0.76901 (9)0.75000.08567 (5)0.0309 (2)
C10.9191 (3)0.75000.00683 (16)0.0187 (6)
C20.9761 (2)0.70181 (7)0.02378 (11)0.0166 (4)
C31.0940 (2)0.70293 (7)0.08762 (12)0.0203 (4)
H3A1.13480.67080.10980.024*
C41.1530 (3)0.75000.11946 (18)0.0243 (6)
H4A1.23360.75000.16290.029*
C50.9115 (2)0.65045 (7)0.00889 (12)0.0175 (4)
C60.9854 (2)0.62594 (7)0.07899 (12)0.0199 (4)
C70.9225 (2)0.57777 (7)0.10680 (12)0.0229 (4)
H7A0.97070.56110.15480.028*
C80.7921 (2)0.55355 (7)0.06661 (12)0.0198 (4)
C90.7221 (2)0.57888 (7)0.00278 (12)0.0207 (4)
H9A0.63280.56270.03090.025*
C100.7782 (2)0.62706 (7)0.03249 (12)0.0187 (4)
C111.1353 (2)0.64923 (8)0.12216 (13)0.0251 (5)
H11A1.15940.68360.09370.030*
C121.1081 (3)0.66018 (10)0.21677 (14)0.0377 (6)
H12A1.01370.68330.22370.057*
H12B1.20480.67730.24070.057*
H12C1.08830.62700.24680.057*
C131.2824 (2)0.61354 (10)0.10894 (14)0.0367 (6)
H13A1.29770.60710.04780.055*
H13B1.26420.58000.13830.055*
H13C1.37970.63050.13230.055*
C140.7274 (2)0.50057 (7)0.09675 (12)0.0225 (4)
H14A0.65180.48730.05160.027*
C150.6292 (3)0.50614 (8)0.17857 (14)0.0336 (5)
H15A0.54300.53220.17010.050*
H15B0.70090.51760.22500.050*
H15C0.58040.47220.19330.050*
C160.8623 (3)0.45979 (8)0.10701 (14)0.0286 (5)
H16A0.92310.45680.05340.043*
H16B0.81430.42570.12140.043*
H16C0.93620.47080.15280.043*
C170.6986 (2)0.65265 (8)0.10990 (13)0.0236 (4)
H17A0.74510.68880.11570.028*
C180.5146 (3)0.65828 (9)0.10040 (14)0.0362 (6)
H18A0.49000.67800.04820.054*
H18B0.46480.62330.09700.054*
H18C0.47070.67710.14990.054*
C190.7407 (3)0.62236 (9)0.19121 (13)0.0355 (5)
H19A0.85910.61920.19630.053*
H19B0.69770.64120.24090.053*
H19D0.69220.58720.18860.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0331 (4)0.0259 (4)0.0336 (4)0.0000.0144 (3)0.000
C10.0173 (13)0.0224 (14)0.0165 (13)0.0000.0020 (10)0.000
C20.0170 (9)0.0155 (9)0.0174 (9)0.0005 (7)0.0034 (7)0.0012 (7)
C30.0223 (10)0.0150 (9)0.0235 (10)0.0027 (8)0.0031 (8)0.0033 (8)
C40.0216 (14)0.0257 (15)0.0256 (15)0.0000.0077 (12)0.000
C50.0171 (9)0.0149 (9)0.0204 (10)0.0012 (7)0.0033 (7)0.0007 (8)
C60.0212 (10)0.0188 (9)0.0197 (10)0.0009 (8)0.0011 (8)0.0002 (8)
C70.0257 (10)0.0218 (10)0.0212 (10)0.0032 (8)0.0000 (8)0.0039 (8)
C80.0211 (10)0.0156 (9)0.0227 (10)0.0000 (8)0.0041 (8)0.0014 (8)
C90.0184 (9)0.0196 (10)0.0242 (10)0.0021 (8)0.0001 (8)0.0022 (8)
C100.0192 (9)0.0167 (9)0.0201 (9)0.0012 (8)0.0012 (8)0.0019 (8)
C110.0261 (11)0.0255 (11)0.0238 (11)0.0066 (9)0.0061 (8)0.0048 (9)
C120.0281 (12)0.0509 (15)0.0341 (13)0.0042 (11)0.0044 (10)0.0133 (11)
C130.0229 (11)0.0532 (15)0.0339 (13)0.0033 (10)0.0025 (9)0.0031 (11)
C140.0236 (10)0.0182 (9)0.0259 (11)0.0029 (8)0.0016 (8)0.0016 (8)
C150.0361 (13)0.0225 (11)0.0422 (13)0.0009 (9)0.0166 (10)0.0055 (10)
C160.0333 (12)0.0187 (10)0.0338 (12)0.0001 (9)0.0053 (10)0.0019 (9)
C170.0234 (10)0.0199 (9)0.0275 (11)0.0037 (8)0.0052 (8)0.0046 (9)
C180.0287 (12)0.0444 (14)0.0355 (13)0.0073 (10)0.0067 (10)0.0051 (11)
C190.0404 (13)0.0442 (13)0.0219 (11)0.0035 (11)0.0009 (10)0.0046 (10)
Geometric parameters (Å, º) top
Cl—C11.745 (3)C7—C81.387 (3)
C1—C2i1.397 (2)C8—C91.388 (3)
C1—C21.397 (2)C8—C141.524 (2)
C2—C31.392 (3)C9—C101.390 (3)
C2—C51.500 (3)C10—C171.524 (3)
C3—C41.385 (2)C11—C121.524 (3)
C4—C3i1.385 (2)C11—C131.526 (3)
C5—C61.401 (3)C14—C151.521 (3)
C5—C101.405 (2)C14—C161.527 (3)
C6—C71.399 (3)C17—C181.526 (3)
C6—C111.525 (3)C17—C191.528 (3)
C2i—C1—C2122.6 (2)C7—C8—C14121.44 (17)
C2i—C1—Cl118.68 (12)C9—C8—C14120.58 (17)
C2—C1—Cl118.68 (12)C8—C9—C10122.29 (18)
C3—C2—C1117.51 (17)C9—C10—C5118.53 (17)
C3—C2—C5120.60 (16)C9—C10—C17120.04 (17)
C1—C2—C5121.87 (17)C5—C10—C17121.40 (16)
C4—C3—C2121.33 (18)C12—C11—C6112.55 (17)
C3i—C4—C3119.7 (3)C12—C11—C13110.91 (17)
C6—C5—C10120.73 (17)C6—C11—C13110.40 (17)
C6—C5—C2120.07 (16)C15—C14—C8111.33 (16)
C10—C5—C2119.19 (16)C15—C14—C16111.10 (16)
C7—C6—C5118.25 (17)C8—C14—C16112.36 (16)
C7—C6—C11120.05 (17)C10—C17—C18112.84 (17)
C5—C6—C11121.65 (16)C10—C17—C19110.52 (16)
C8—C7—C6122.21 (18)C18—C17—C19110.66 (17)
C7—C8—C9117.98 (17)
Symmetry code: (i) x, y+3/2, z.
(II) top
Crystal data top
C36H49BrDx = 1.100 Mg m3
Mr = 561.66Melting point = 211–213 K
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 934 reflections
a = 8.2823 (14) Åθ = 2.9–24.6°
b = 25.831 (4) ŵ = 1.23 mm1
c = 15.856 (3) ÅT = 293 K
V = 3392.2 (10) Å3Needle, colourless
Z = 40.78 × 0.30 × 0.20 mm
F(000) = 1200
Data collection top
Siemens SMART 1000
diffractometer
3054 independent reflections
Radiation source: normal-focus sealed tube2418 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1999)
h = 99
Tmin = 0.447, Tmax = 0.791k = 2530
23472 measured reflectionsl = 1818
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-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 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.40 e Å3
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
Br10.24164 (5)0.25000.08168 (3)0.06490 (18)
C10.0743 (4)0.25000.0012 (2)0.0414 (8)
C20.0161 (3)0.20251 (9)0.02953 (15)0.0418 (5)
C30.1037 (3)0.20376 (10)0.09109 (17)0.0508 (6)
H3A0.14540.17280.11170.061*
C40.1617 (5)0.25000.1220 (3)0.0594 (10)
H4A0.24020.25000.16390.071*
C50.0775 (3)0.15204 (9)0.00404 (16)0.0453 (6)
C100.2068 (3)0.12733 (10)0.03584 (19)0.0528 (7)
C90.2638 (4)0.08101 (11)0.0030 (2)0.0665 (8)
H9A0.34990.06470.02960.080*
C80.1980 (4)0.05838 (12)0.0674 (2)0.0697 (9)
C70.0710 (4)0.08338 (12)0.1060 (2)0.0725 (9)
H7A0.02590.06870.15400.087*
C60.0065 (3)0.13033 (11)0.07565 (17)0.0560 (7)
C110.2841 (4)0.14968 (13)0.1152 (2)0.0703 (9)
H11A0.23360.18330.12600.084*
C120.4644 (5)0.15880 (19)0.1050 (3)0.1154 (16)
H12A0.48310.18060.05690.173*
H12B0.50590.17540.15470.173*
H12C0.51810.12620.09700.173*
C130.2518 (5)0.1156 (2)0.1914 (3)0.1123 (15)
H13A0.13740.11130.19840.168*
H13B0.30130.08240.18310.168*
H13C0.29620.13160.24090.168*
C140.2622 (5)0.00737 (14)0.1019 (3)0.1032 (15)
H14A0.33530.00250.05600.124*
C150.1514 (7)0.03449 (14)0.0987 (3)0.131 (2)
H15A0.20350.06550.11800.196*
H15B0.11540.03930.04160.196*
H15C0.06040.02700.13410.196*
C160.3750 (6)0.01304 (15)0.1686 (3)0.135 (2)
H16A0.45590.03780.15280.203*
H16B0.42520.01970.17990.203*
H16C0.32000.02490.21830.203*
C170.1374 (4)0.15552 (14)0.1187 (2)0.0784 (10)
H17A0.15770.18860.09040.094*
C180.2889 (5)0.1220 (2)0.1082 (3)0.1263 (19)
H18A0.38120.14040.12900.190*
H18B0.27610.09040.13940.190*
H18C0.30420.11400.04960.190*
C190.1076 (6)0.16682 (18)0.2114 (3)0.1134 (15)
H19A0.19670.18620.23380.170*
H19B0.01010.18660.21730.170*
H19C0.09710.13480.24160.170*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0728 (3)0.0520 (3)0.0700 (3)0.0000.0348 (2)0.000
C10.0409 (18)0.0421 (19)0.0411 (18)0.0000.0078 (14)0.000
C20.0437 (13)0.0367 (13)0.0451 (14)0.0009 (10)0.0014 (11)0.0004 (10)
C30.0532 (15)0.0403 (14)0.0589 (16)0.0065 (11)0.0105 (12)0.0046 (12)
C40.056 (2)0.059 (3)0.063 (3)0.0000.023 (2)0.000
C50.0502 (14)0.0347 (12)0.0510 (15)0.0043 (11)0.0090 (12)0.0012 (11)
C100.0539 (15)0.0396 (14)0.0649 (18)0.0002 (12)0.0046 (13)0.0001 (13)
C90.0652 (19)0.0459 (16)0.088 (2)0.0075 (14)0.0118 (16)0.0013 (15)
C80.073 (2)0.0464 (17)0.090 (2)0.0009 (15)0.0246 (18)0.0092 (16)
C70.091 (2)0.0619 (19)0.0650 (19)0.0180 (18)0.0105 (17)0.0249 (16)
C60.0627 (17)0.0482 (15)0.0571 (16)0.0042 (13)0.0030 (13)0.0079 (13)
C110.0674 (19)0.0614 (19)0.082 (2)0.0137 (15)0.0161 (17)0.0087 (17)
C120.081 (3)0.141 (4)0.125 (4)0.030 (3)0.022 (3)0.007 (3)
C130.116 (4)0.149 (4)0.072 (3)0.019 (3)0.006 (2)0.004 (3)
C140.121 (3)0.0505 (19)0.138 (4)0.006 (2)0.057 (3)0.031 (2)
C150.164 (4)0.050 (2)0.179 (5)0.008 (3)0.087 (4)0.017 (3)
C160.158 (4)0.069 (3)0.179 (5)0.004 (3)0.099 (4)0.027 (3)
C170.084 (2)0.089 (2)0.062 (2)0.0058 (19)0.0160 (17)0.0201 (18)
C180.077 (3)0.195 (6)0.107 (3)0.009 (3)0.008 (2)0.026 (4)
C190.118 (3)0.134 (4)0.089 (3)0.009 (3)0.016 (3)0.023 (3)
Geometric parameters (Å, º) top
Br1—C11.910 (3)C9—C81.372 (5)
C1—C2i1.393 (3)C8—C71.378 (5)
C1—C21.393 (3)C8—C141.523 (4)
C2—C31.392 (3)C7—C61.410 (4)
C2—C51.497 (3)C6—C171.519 (4)
C3—C41.378 (3)C11—C131.518 (6)
C4—C3i1.378 (3)C11—C121.520 (5)
C5—C61.396 (4)C14—C161.419 (5)
C5—C101.398 (4)C14—C151.419 (6)
C10—C91.388 (4)C17—C191.519 (5)
C10—C111.526 (5)C17—C181.535 (6)
C2i—C1—C2123.5 (3)C9—C8—C14121.5 (4)
C2i—C1—Br1118.25 (15)C7—C8—C14120.8 (4)
C2—C1—Br1118.25 (15)C8—C7—C6122.8 (3)
C3—C2—C1116.9 (2)C5—C6—C7117.6 (3)
C3—C2—C5120.8 (2)C5—C6—C17121.6 (3)
C1—C2—C5122.3 (2)C7—C6—C17120.9 (3)
C4—C3—C2121.2 (2)C13—C11—C12110.3 (3)
C3—C4—C3i120.2 (3)C13—C11—C10111.3 (3)
C6—C5—C10120.5 (2)C12—C11—C10112.5 (3)
C6—C5—C2119.7 (2)C16—C14—C15122.1 (4)
C10—C5—C2119.8 (2)C16—C14—C8114.1 (3)
C9—C10—C5119.0 (3)C15—C14—C8114.9 (3)
C9—C10—C11119.6 (3)C19—C17—C6112.9 (3)
C5—C10—C11121.5 (2)C19—C17—C18110.3 (3)
C8—C9—C10122.5 (3)C6—C17—C18110.5 (3)
C9—C8—C7117.7 (3)
Symmetry code: (i) x, y+1/2, z.
(III) top
Crystal data top
C36H49IDx = 1.221 Mg m3
Mr = 608.65Melting point = 229–230 K
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 50 reflections
a = 8.1100 (13) Åθ = 4.7–14.7°
b = 25.549 (6) ŵ = 0.99 mm1
c = 15.978 (6) ÅT = 130 K
V = 3310.7 (16) Å3Parallelepiped, colourless
Z = 40.76 × 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 tubeRint = 0.045
Graphite monochromatorθmax = 27.5°, θmin = 1.5°
ω scansh = 010
Absorption correction: empirical
(XABS2; Parkin et al., 1995)
k = 033
Tmin = 0.521, Tmax = 0.756l = 020
8539 measured reflections2 standard reflections every 198 reflections
3891 independent reflections intensity decay: 1%
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)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-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 parametersΔρmax = 0.97 e Å3
0 restraintsΔρmin = 0.94 e Å3
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
I11.22084 (6)0.25000.41305 (3)0.02783 (19)
C11.4154 (6)0.25000.4997 (3)0.0087 (9)
C21.4756 (5)0.20210 (14)0.5294 (2)0.0073 (7)
C31.5976 (5)0.20280 (15)0.5910 (2)0.0122 (7)
H3A1.64010.17070.61180.015*
C41.6581 (8)0.25000.6225 (4)0.0153 (11)
H4A1.73980.25000.66510.018*
C51.4130 (4)0.15090 (13)0.4969 (2)0.0077 (7)
C101.2802 (5)0.12595 (15)0.5370 (2)0.0098 (7)
C91.2222 (5)0.07846 (16)0.5059 (2)0.0124 (7)
H9A1.13260.06170.53320.015*
C81.2917 (5)0.05509 (15)0.4361 (3)0.0128 (7)
C71.4233 (5)0.08049 (15)0.3964 (2)0.0129 (7)
H7A1.47100.06510.34800.016*
C61.4863 (5)0.12782 (15)0.4260 (2)0.0113 (7)
C111.6357 (5)0.15249 (17)0.3838 (3)0.0175 (8)
H11A1.65930.18660.41210.021*
C121.6046 (7)0.1634 (2)0.2913 (3)0.0331 (12)
H12A1.50770.18600.28540.050*
H12B1.58500.13020.26200.050*
H12C1.70110.18080.26710.050*
C131.7865 (6)0.1171 (3)0.3942 (3)0.0311 (12)
H13A1.80510.11030.45390.047*
H13B1.88370.13440.37050.047*
H13C1.76750.08390.36510.047*
C141.2256 (5)0.00332 (17)0.4027 (3)0.0160 (8)
H14A1.14510.01020.44490.019*
C151.1324 (7)0.01049 (19)0.3213 (3)0.0293 (11)
H15A1.09170.02350.30180.044*
H15B1.20620.02550.27910.044*
H15C1.03890.03410.33040.044*
C161.3613 (6)0.03780 (16)0.3938 (3)0.0220 (9)
H16A1.31370.07040.37230.033*
H16B1.41160.04430.44860.033*
H16C1.44560.02510.35480.033*
C171.2017 (5)0.14941 (16)0.6154 (3)0.0149 (8)
H17A1.24790.18540.62320.018*
C191.0140 (6)0.1543 (2)0.6081 (3)0.0277 (11)
H19A0.96960.16940.65970.042*
H19B0.96590.11950.59920.042*
H19C0.98660.17700.56070.042*
C181.2465 (7)0.1173 (2)0.6920 (3)0.0294 (11)
H18A1.36680.11440.69600.044*
H18B1.19800.08230.68720.044*
H18C1.20380.13460.74230.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0289 (3)0.0264 (3)0.0282 (3)0.0000.01479 (18)0.000
C10.005 (2)0.010 (2)0.011 (2)0.0000.0019 (18)0.000
C20.0042 (16)0.0099 (15)0.0079 (15)0.0017 (13)0.0018 (12)0.0005 (12)
C30.0092 (18)0.0120 (16)0.0153 (18)0.0019 (14)0.0040 (14)0.0013 (13)
C40.016 (3)0.015 (2)0.015 (3)0.0000.009 (2)0.000
C50.0055 (16)0.0088 (15)0.0087 (16)0.0004 (13)0.0024 (13)0.0005 (12)
C100.0040 (16)0.0139 (16)0.0114 (17)0.0019 (14)0.0010 (13)0.0001 (13)
C90.0077 (17)0.0155 (17)0.0140 (17)0.0015 (15)0.0012 (14)0.0009 (14)
C80.0097 (18)0.0123 (16)0.0164 (18)0.0022 (14)0.0039 (15)0.0007 (14)
C70.0135 (19)0.0157 (17)0.0096 (16)0.0015 (15)0.0026 (14)0.0040 (14)
C60.0080 (18)0.0135 (17)0.0123 (17)0.0022 (14)0.0047 (13)0.0005 (13)
C110.016 (2)0.0228 (19)0.0137 (18)0.0067 (16)0.0105 (16)0.0025 (16)
C120.023 (2)0.051 (3)0.026 (2)0.002 (2)0.008 (2)0.019 (2)
C130.011 (2)0.056 (3)0.026 (2)0.002 (2)0.0017 (18)0.006 (2)
C140.017 (2)0.0142 (18)0.0165 (19)0.0050 (16)0.0014 (16)0.0036 (14)
C150.027 (3)0.022 (2)0.039 (3)0.0011 (19)0.022 (2)0.006 (2)
C160.024 (2)0.0136 (18)0.028 (2)0.0012 (17)0.0101 (19)0.0025 (16)
C170.0110 (19)0.0192 (18)0.0145 (18)0.0003 (15)0.0079 (15)0.0037 (15)
C190.013 (2)0.050 (3)0.021 (2)0.010 (2)0.0046 (17)0.000 (2)
C180.029 (3)0.048 (3)0.012 (2)0.007 (2)0.0010 (18)0.003 (2)
Geometric parameters (Å, º) top
I1—C12.099 (5)C9—C81.385 (6)
C1—C2i1.401 (4)C8—C71.401 (6)
C1—C21.401 (4)C8—C141.523 (5)
C2—C31.395 (5)C7—C61.395 (5)
C2—C51.496 (5)C6—C111.523 (5)
C3—C41.396 (5)C11—C121.524 (6)
C4—C3i1.396 (5)C11—C131.530 (7)
C5—C101.407 (5)C14—C151.516 (6)
C5—C61.409 (5)C14—C161.528 (6)
C10—C91.393 (5)C17—C181.517 (7)
C10—C171.527 (5)C17—C191.532 (6)
C2i—C1—C2121.8 (5)C9—C8—C14120.8 (4)
C2i—C1—I1119.1 (2)C7—C8—C14120.8 (4)
C2—C1—I1119.1 (2)C6—C7—C8121.8 (4)
C3—C2—C1118.4 (4)C7—C6—C5118.8 (3)
C3—C2—C5119.8 (3)C7—C6—C11120.0 (3)
C1—C2—C5121.8 (3)C5—C6—C11121.2 (3)
C2—C3—C4121.0 (4)C6—C11—C12111.9 (4)
C3—C4—C3i119.5 (5)C6—C11—C13110.1 (4)
C10—C5—C6120.0 (3)C12—C11—C13110.2 (4)
C10—C5—C2119.9 (3)C15—C14—C8111.8 (4)
C6—C5—C2120.1 (3)C15—C14—C16111.2 (4)
C9—C10—C5119.4 (3)C8—C14—C16112.1 (3)
C9—C10—C17119.6 (3)C18—C17—C10110.5 (4)
C5—C10—C17121.0 (3)C18—C17—C19110.1 (4)
C8—C9—C10121.7 (4)C10—C17—C19112.5 (4)
C9—C8—C7118.4 (4)
Symmetry code: (i) x, y+1/2, z.
 

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