A ter­phenyl halide series: 2,6-Trip₂­H₃C₆X (Trip = 2,4,6-triiso­propyl­phenyl; X = Cl, Br, I)

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.

Computing details

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)

Crystal data

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) Å^3	Needle, colourless
Z = 4	0.32 × 0.15 × 0.04 mm
F(000) = 1128

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.128	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.066P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Cl—C1	1.745 (3)	C7—C8	1.387 (3)
C1—C2^i	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—C3^i	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)
C2^i—C1—C2	122.6 (2)	C7—C8—C14	121.44 (17)
C2^i—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)
C3^i—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.

(II)

Crystal data

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) Å^3	Needle, colourless
Z = 4	0.78 × 0.30 × 0.20 mm
F(000) = 1200

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0522P)^2 + 2.2426P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Br1—C1	1.910 (3)	C9—C8	1.372 (5)
C1—C2^i	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—C3^i	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)
C2^i—C1—C2	123.5 (3)	C9—C8—C14	121.5 (4)
C2^i—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—C3^i	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.

(III)

Crystal data

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) Å^3	Parallelepiped, colourless
Z = 4	0.76 × 0.36 × 0.30 mm
F(000) = 1272

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.111P)^2 + 10.4168P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

I1—C1	2.099 (5)	C9—C8	1.385 (6)
C1—C2^i	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—C3^i	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)
C2^i—C1—C2	121.8 (5)	C9—C8—C14	120.8 (4)
C2^i—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—C3^i	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.