Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105014114/bs5015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105014114/bs5015sup2.fcf | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768105014114/bs5015sup3.pdf |
CCDC reference: 280357
Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C20H16Cl2Zr | F(000) = 840 |
Mr = 418.45 | Dx = 1.696 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 40 reflections |
a = 15.3870 (5) Å | θ = 30.0–35.0° |
b = 10.5120 (5) Å | µ = 0.99 mm−1 |
c = 11.9270 (5) Å | T = 100 K |
β = 121.85 (1)° | Sphere, colourless |
V = 1638.7 (2) Å3 | 0.09 mm (radius) |
Z = 4 |
MacScience four-circle diffractometer | 6151 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.020 |
Graphite monochromator | θmax = 50.0°, θmin = 2.5° |
ω/2θ? scans | h = −33→28 |
Absorption correction: for a sphere Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. | k = −22→18 |
Tmin = 0.861, Tmax = 0.863 | l = −19→25 |
10224 measured reflections | 3 standard reflections every 30 reflections |
6602 independent reflections | intensity decay: 1.5% |
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)] = 0.030 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.072 | All H-atom parameters refined |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0356P)2 + 1.3284P] where P = (Fo2 + 2Fc2)/3 |
6602 reflections | (Δ/σ)max = 0.002 |
137 parameters | Δρmax = 1.37 e Å−3 |
0 restraints | Δρmin = −1.44 e Å−3 |
C20H16Cl2Zr | V = 1638.7 (2) Å3 |
Mr = 418.45 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 15.3870 (5) Å | µ = 0.99 mm−1 |
b = 10.5120 (5) Å | T = 100 K |
c = 11.9270 (5) Å | 0.09 mm (radius) |
β = 121.85 (1)° |
MacScience four-circle diffractometer | 6151 reflections with I > 2σ(I) |
Absorption correction: for a sphere Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. | Rint = 0.020 |
Tmin = 0.861, Tmax = 0.863 | 3 standard reflections every 30 reflections |
10224 measured reflections | intensity decay: 1.5% |
6602 independent reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.072 | All H-atom parameters refined |
S = 1.02 | Δρmax = 1.37 e Å−3 |
6602 reflections | Δρmin = −1.44 e Å−3 |
137 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Zr | 0.0000 | 0.271052 (11) | 0.2500 | 0.01012 (2) | |
Cl | −0.136622 (17) | 0.42390 (2) | 0.18359 (2) | 0.01786 (4) | |
C1 | −0.00110 (7) | 0.07448 (8) | 0.13263 (9) | 0.01541 (12) | |
C2 | −0.09921 (7) | 0.13235 (10) | 0.05610 (9) | 0.01863 (14) | |
C3 | −0.09025 (8) | 0.24789 (10) | 0.00163 (9) | 0.01878 (15) | |
C3A | 0.01377 (7) | 0.26199 (9) | 0.04028 (8) | 0.01545 (12) | |
C4 | 0.06545 (10) | 0.35219 (10) | 0.00658 (10) | 0.02057 (16) | |
C5 | 0.16749 (10) | 0.33535 (11) | 0.05609 (12) | 0.02325 (18) | |
C6 | 0.22272 (9) | 0.23071 (12) | 0.13963 (12) | 0.02224 (16) | |
C7 | 0.17584 (8) | 0.14142 (10) | 0.17323 (10) | 0.01779 (13) | |
C7A | 0.06909 (7) | 0.15477 (8) | 0.12271 (8) | 0.01380 (11) | |
C8 | 0.02332 (10) | −0.04865 (9) | 0.20705 (11) | 0.02108 (16) | |
H2 | −0.1615 (16) | 0.102 (2) | 0.040 (2) | 0.029 (5)* | |
H3 | −0.1394 (15) | 0.301 (2) | −0.047 (2) | 0.025 (5)* | |
H4 | 0.0289 (15) | 0.4190 (19) | −0.0500 (19) | 0.020 (4)* | |
H5 | 0.2021 (18) | 0.390 (2) | 0.038 (2) | 0.039 (6)* | |
H6 | 0.2965 (17) | 0.222 (2) | 0.169 (2) | 0.027 (5)* | |
H7 | 0.2130 (16) | 0.070 (2) | 0.222 (2) | 0.028 (5)* | |
H81 | 0.1003 (15) | −0.0621 (19) | 0.2686 (19) | 0.022 (4)* | |
H82 | 0.0010 (15) | −0.118 (2) | 0.1477 (19) | 0.026 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zr | 0.00990 (4) | 0.01098 (4) | 0.00911 (4) | 0.000 | 0.00476 (3) | 0.000 |
Cl | 0.01714 (8) | 0.02022 (9) | 0.01815 (8) | 0.00735 (6) | 0.01064 (7) | 0.00518 (6) |
C1 | 0.0193 (3) | 0.0130 (3) | 0.0150 (3) | −0.0007 (2) | 0.0098 (3) | −0.0019 (2) |
C2 | 0.0166 (3) | 0.0210 (4) | 0.0153 (3) | −0.0029 (3) | 0.0063 (3) | −0.0051 (3) |
C3 | 0.0182 (3) | 0.0229 (4) | 0.0105 (2) | 0.0050 (3) | 0.0044 (2) | 0.0001 (2) |
C3A | 0.0210 (3) | 0.0149 (3) | 0.0115 (2) | 0.0032 (2) | 0.0093 (2) | 0.0012 (2) |
C4 | 0.0350 (5) | 0.0151 (3) | 0.0189 (3) | 0.0030 (3) | 0.0192 (4) | 0.0025 (3) |
C5 | 0.0342 (5) | 0.0204 (4) | 0.0270 (4) | −0.0036 (4) | 0.0243 (4) | −0.0019 (3) |
C6 | 0.0233 (4) | 0.0247 (4) | 0.0262 (4) | −0.0007 (3) | 0.0182 (3) | −0.0026 (4) |
C7 | 0.0192 (3) | 0.0184 (3) | 0.0185 (3) | 0.0044 (3) | 0.0118 (3) | 0.0008 (3) |
C7A | 0.0178 (3) | 0.0128 (3) | 0.0125 (2) | 0.0019 (2) | 0.0091 (2) | 0.0003 (2) |
C8 | 0.0338 (5) | 0.0120 (3) | 0.0253 (4) | 0.0018 (3) | 0.0209 (4) | 0.0003 (3) |
Zr—Cli | 2.4230 (5) | C1—C2 | 1.4241 (15) |
Zr—Cl | 2.4230 (5) | C1—C7A | 1.4240 (13) |
Zr—C2 | 2.4655 (12) | C1—C8 | 1.5008 (14) |
Zr—C2i | 2.4655 (12) | C2—C3 | 1.4180 (16) |
Zr—C1 | 2.4910 (9) | C3—C3A | 1.4204 (15) |
Zr—C1i | 2.4910 (9) | C3A—C4 | 1.4250 (14) |
Zr—C3 | 2.5341 (12) | C3A—C7A | 1.4415 (12) |
Zr—C3i | 2.5341 (12) | C4—C5 | 1.3664 (18) |
Zr—C7Ai | 2.5754 (9) | C5—C6 | 1.4253 (18) |
Zr—C7A | 2.5754 (9) | C6—C7 | 1.3664 (15) |
Zr—C3A | 2.6210 (9) | C7—C7A | 1.4269 (13) |
Zr—C3Ai | 2.6210 (9) | C8—C8i | 1.530 (2) |
Cli—Zr—Cl | 96.92 (2) | C2i—Zr—C3A | 123.49 (3) |
Cli—Zr—C2 | 134.40 (3) | C1—Zr—C3A | 54.09 (3) |
Cl—Zr—C2 | 94.85 (4) | C1i—Zr—C3A | 121.75 (3) |
Cli—Zr—C2i | 94.85 (4) | C3—Zr—C3A | 31.93 (3) |
Cl—Zr—C2i | 134.40 (3) | C3i—Zr—C3A | 147.32 (3) |
C2—Zr—C2i | 107.49 (6) | C7Ai—Zr—C3A | 144.26 (3) |
Cli—Zr—C1 | 118.76 (3) | C7A—Zr—C3A | 32.20 (3) |
Cl—Zr—C1 | 128.24 (3) | Cli—Zr—C3Ai | 101.84 (3) |
C2—Zr—C1 | 33.39 (3) | Cl—Zr—C3Ai | 80.97 (3) |
C2i—Zr—C1 | 81.59 (4) | C2—Zr—C3Ai | 123.49 (3) |
Cli—Zr—C1i | 128.24 (3) | C2i—Zr—C3Ai | 53.50 (3) |
Cl—Zr—C1i | 118.76 (3) | C1—Zr—C3Ai | 121.75 (3) |
C2—Zr—C1i | 81.59 (4) | C1i—Zr—C3Ai | 54.09 (3) |
C2i—Zr—C1i | 33.39 (3) | C3—Zr—C3Ai | 147.32 (3) |
C1—Zr—C1i | 67.90 (4) | C3i—Zr—C3Ai | 31.93 (3) |
Cli—Zr—C3 | 106.95 (4) | C7Ai—Zr—C3Ai | 32.20 (3) |
Cl—Zr—C3 | 80.55 (4) | C7A—Zr—C3Ai | 144.26 (3) |
C2—Zr—C3 | 32.92 (4) | C3A—Zr—C3Ai | 175.83 (4) |
C2i—Zr—C3 | 136.54 (4) | C2—C1—C7A | 106.71 (8) |
C1—Zr—C3 | 54.99 (3) | C2—C1—C8 | 126.68 (9) |
C1i—Zr—C3 | 114.47 (3) | C7A—C1—C8 | 126.60 (9) |
Cli—Zr—C3i | 80.55 (4) | C2—C1—Zr | 72.32 (6) |
Cl—Zr—C3i | 106.95 (4) | C7A—C1—Zr | 76.97 (5) |
C2—Zr—C3i | 136.54 (4) | C8—C1—Zr | 117.24 (6) |
C2i—Zr—C3i | 32.92 (4) | C3—C2—C1 | 109.46 (9) |
C1—Zr—C3i | 114.47 (3) | C3—C2—Zr | 76.20 (6) |
C1i—Zr—C3i | 54.99 (3) | C1—C2—Zr | 74.29 (6) |
C3—Zr—C3i | 168.97 (5) | C2—C3—C3A | 107.82 (8) |
Cli—Zr—C7Ai | 132.75 (3) | C2—C3—Zr | 70.88 (5) |
Cl—Zr—C7Ai | 87.17 (3) | C3A—C3—Zr | 77.41 (6) |
C2—Zr—C7Ai | 91.63 (3) | C3—C3A—C4 | 132.75 (9) |
C2i—Zr—C7Ai | 53.86 (3) | C3—C3A—C7A | 107.37 (8) |
C1—Zr—C7Ai | 93.16 (3) | C4—C3A—C7A | 119.74 (9) |
C1i—Zr—C7Ai | 32.59 (3) | C3—C3A—Zr | 70.66 (6) |
C3—Zr—C7Ai | 120.10 (4) | C4—C3A—Zr | 125.68 (6) |
C3i—Zr—C7Ai | 53.65 (3) | C7A—C3A—Zr | 72.16 (5) |
Cli—Zr—C7A | 87.17 (3) | C5—C4—C3A | 118.48 (9) |
Cl—Zr—C7A | 132.75 (3) | C4—C5—C6 | 121.83 (10) |
C2—Zr—C7A | 53.86 (3) | C7—C6—C5 | 121.52 (10) |
C2i—Zr—C7A | 91.63 (3) | C6—C7—C7A | 118.48 (9) |
C1—Zr—C7A | 32.59 (3) | C1—C7A—C7 | 131.38 (8) |
C1i—Zr—C7A | 93.16 (3) | C1—C7A—C3A | 108.62 (8) |
C3—Zr—C7A | 53.65 (3) | C7—C7A—C3A | 119.92 (8) |
C3i—Zr—C7A | 120.10 (4) | C1—C7A—Zr | 70.44 (5) |
C7Ai—Zr—C7A | 123.33 (4) | C7—C7A—Zr | 122.61 (6) |
Cli—Zr—C3A | 80.97 (3) | C3A—C7A—Zr | 75.64 (5) |
Cl—Zr—C3A | 101.84 (3) | C1—C8—C8i | 109.67 (7) |
C2—Zr—C3A | 53.50 (3) |
Symmetry code: (i) −x, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H16Cl2Zr |
Mr | 418.45 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 100 |
a, b, c (Å) | 15.3870 (5), 10.5120 (5), 11.9270 (5) |
β (°) | 121.85 (1) |
V (Å3) | 1638.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.99 |
Crystal size (mm) | 0.09 (radius) |
Data collection | |
Diffractometer | MacScience four-circle diffractometer |
Absorption correction | For a sphere Interpolation using Int.Tab. Vol. C (1992) p. 523,Tab. 6.3.3.3 for values of muR in the range 0-2.5, and Int.Tab. Vol.II (1959) p.302; Table 5.3.6 B for muR in the range 2.6-10.0. The interpolation procedure of C.W.Dwiggins Jr (Acta Cryst.(1975) A31,146-148) is used with some modification. |
Tmin, Tmax | 0.861, 0.863 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10224, 6602, 6151 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 1.077 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.072, 1.02 |
No. of reflections | 6602 |
No. of parameters | 137 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 1.37, −1.44 |
Computer programs: SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).