Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807018582/ez2074sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807018582/ez2074TSFsup2.hkl |
CCDC reference: 647193
Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL and PLATON.
C6H4Se4 | Z = 3 |
Mr = 391.93 | F(000) = 528 |
Triclinic, P1 | Dx = 2.985 Mg m−3 |
Hall symbol: -P 1 | Melting point: 406 K |
a = 8.6303 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6454 (3) Å | Cell parameters from 5298 reflections |
c = 10.4231 (3) Å | θ = 2.7–28.0° |
α = 105.245 (1)° | µ = 16.75 mm−1 |
β = 106.382 (1)° | T = 120 K |
γ = 108.221 (1)° | Block, red |
V = 653.98 (4) Å3 | 0.16 × 0.15 × 0.08 mm |
Bruker SMART APEX CCD area-detector diffractometer | 3143 independent reflections |
Radiation source: fine-focus sealed tube | 2844 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω scans | θmax = 28.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −11→11 |
Tmin = 0.170, Tmax = 0.262 | k = −11→11 |
7739 measured reflections | l = −13→13 |
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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.051 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.03P)2 + 0.1634P] where P = (Fo2 + 2Fc2)/3 |
3143 reflections | (Δ/σ)max = 0.002 |
136 parameters | Δρmax = 0.69 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
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. Short Se···Se distances 3.5329 (0.0004) Se1 - Se5_$3 3.5829 (0.0004) Se3 - Se5_$4 3.3797 (0.0005) Se4 - Se4_$5 EQIV $3 x, y, z + 1 EQIV $4 x, y - 1, z EQIV $5 - x + 1, -y + 1, -z + 2 Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.3874 (0.0097) x - 6.4715 (0.0042) y + 8.6839 (0.0049) z = 7.2877 (0.0062) * 0.0006 (0.0007) Se1 * -0.0006 (0.0007) Se2 * -0.0014 (0.0017) C3 * 0.0014 (0.0017) C4 Rms deviation of fitted atoms = 0.0011 2.6881 (0.0016) x - 7.0863 (0.0005) y + 7.2732 (0.0013) z = 5.6094 (0.0013) Angle to previous plane (with approximate e.s.d.) = 15.76 (0.07) * -0.0108 (0.0006) Se1 * 0.0007 (0.0006) Se2 * -0.0132 (0.0007) Se3 * -0.0015 (0.0007) Se4 * 0.0063 (0.0020) C1 * 0.0185 (0.0020) C2 - 0.4543 (0.0029) C3 - 0.4470 (0.0028) C4 - 0.7967 (0.0028) C5 - 0.7961 (0.0028) C6 Rms deviation of fitted atoms = 0.0106 6.2376 (0.0066) x - 6.8145 (0.0033) y + 3.4479 (0.0101) z = 3.2446 (0.0067) Angle to previous plane (with approximate e.s.d.) = 28.54 (0.07) * 0.0003 (0.0007) Se3 * -0.0002 (0.0007) Se4 * -0.0006 (0.0016) C5 * 0.0006 (0.0016) C6 Rms deviation of fitted atoms = 0.0005 - 1.8511 (0.0082) x + 5.9848 (0.0041) y + 4.7538 (0.0091) z = 5.4306 (0.0007) Angle to previous plane (with approximate e.s.d.) = 73.31 (0.07) * 0.0003 (0.0007) Se5 * -0.0003 (0.0007) Se6 * -0.0007 (0.0016) C8 * 0.0007 (0.0016) C9 Rms deviation of fitted atoms = 0.0005 - 2.1118 (0.0146) x + 5.8723 (0.0065) y + 5.0395 (0.0157) z = 5.4491 (0.0009) Angle to previous plane (with approximate e.s.d.) = 2.29 (0.23) * 0.0000 (0.0000) Se5 * 0.0000 (0.0000) Se6 * 0.0000 (0.0000) C7 - 0.0663 (0.0046) C8 - 0.0645 (0.0045) C9 Rms deviation of fitted atoms = 0.0000 2.6881 (0.0016) x - 7.0863 (0.0005) y + 7.2732 (0.0013) z = 5.6094 (0.0013) Angle to previous plane (with approximate e.s.d.) = 81.90 (0.07) * -0.0108 (0.0006) Se1 * 0.0007 (0.0006) Se2 * -0.0132 (0.0007) Se3 * -0.0015 (0.0007) Se4 * 0.0063 (0.0020) C1 * 0.0185 (0.0020) C2 - 0.4543 (0.0029) C3 - 0.4470 (0.0028) C4 - 0.7967 (0.0028) C5 - 0.7961 (0.0028) C6 Rms deviation of fitted atoms = 0.0106 |
Refinement. Friedel pairs were merged before refinement. |
x | y | z | Uiso*/Ueq | ||
Se1 | −0.01014 (3) | 0.28911 (3) | 1.05519 (3) | 0.01379 (7) | |
Se2 | −0.26604 (3) | −0.08138 (3) | 0.79037 (3) | 0.01477 (7) | |
Se3 | 0.07536 (3) | −0.06305 (3) | 0.68016 (3) | 0.01535 (7) | |
Se4 | 0.32861 (3) | 0.30248 (3) | 0.94430 (3) | 0.01401 (7) | |
C1 | −0.0356 (3) | 0.1074 (3) | 0.8899 (3) | 0.0109 (4) | |
C2 | 0.0978 (3) | 0.1124 (3) | 0.8471 (3) | 0.0127 (5) | |
C3 | −0.2588 (3) | 0.2015 (4) | 1.0008 (3) | 0.0184 (5) | |
H3 | −0.3076 | 0.2675 | 1.0518 | 0.022* | |
C4 | −0.3651 (3) | 0.0479 (4) | 0.8913 (3) | 0.0191 (5) | |
H4 | −0.4901 | 0.0030 | 0.8639 | 0.023* | |
C5 | 0.2644 (3) | 0.1012 (4) | 0.6626 (3) | 0.0169 (5) | |
H5 | 0.2829 | 0.0741 | 0.5753 | 0.020* | |
C6 | 0.3708 (3) | 0.2538 (4) | 0.7721 (3) | 0.0164 (5) | |
H6 | 0.4665 | 0.3375 | 0.7647 | 0.020* | |
Se5 | 0.02616 (3) | 0.64448 (3) | 0.34125 (3) | 0.01437 (7) | |
Se6 | 0.29945 (3) | 0.55665 (4) | 0.55812 (3) | 0.01782 (7) | |
C7 | 0.0632 (3) | 0.5391 (3) | 0.4796 (3) | 0.0116 (5) | |
C8 | 0.2605 (4) | 0.7085 (4) | 0.3518 (3) | 0.0184 (5) | |
H8 | 0.2976 | 0.7664 | 0.2929 | 0.022* | |
C9 | 0.3741 (3) | 0.6719 (4) | 0.4423 (3) | 0.0193 (5) | |
H9 | 0.4924 | 0.7041 | 0.4482 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.01285 (12) | 0.01268 (12) | 0.01578 (13) | 0.00605 (10) | 0.00673 (10) | 0.00340 (10) |
Se2 | 0.00852 (12) | 0.01447 (13) | 0.01706 (13) | 0.00230 (9) | 0.00372 (9) | 0.00429 (10) |
Se3 | 0.01540 (13) | 0.01191 (12) | 0.01503 (13) | 0.00303 (10) | 0.00771 (10) | 0.00117 (10) |
Se4 | 0.00950 (12) | 0.01339 (12) | 0.01402 (13) | 0.00120 (9) | 0.00481 (9) | 0.00193 (10) |
C1 | 0.0101 (11) | 0.0090 (11) | 0.0126 (11) | 0.0040 (9) | 0.0038 (9) | 0.0033 (9) |
C2 | 0.0099 (11) | 0.0120 (11) | 0.0135 (11) | 0.0034 (9) | 0.0036 (9) | 0.0032 (9) |
C3 | 0.0144 (12) | 0.0236 (14) | 0.0227 (13) | 0.0114 (10) | 0.0100 (10) | 0.0099 (11) |
C4 | 0.0127 (12) | 0.0247 (14) | 0.0250 (14) | 0.0100 (11) | 0.0091 (10) | 0.0127 (11) |
C5 | 0.0150 (12) | 0.0219 (13) | 0.0156 (12) | 0.0065 (10) | 0.0091 (10) | 0.0082 (10) |
C6 | 0.0127 (12) | 0.0212 (13) | 0.0203 (13) | 0.0071 (10) | 0.0113 (10) | 0.0102 (11) |
Se5 | 0.01445 (13) | 0.01702 (13) | 0.01601 (12) | 0.00880 (10) | 0.00757 (10) | 0.00849 (10) |
Se6 | 0.01077 (12) | 0.02520 (15) | 0.02210 (14) | 0.00833 (10) | 0.00734 (10) | 0.01406 (11) |
C7 | 0.0100 (11) | 0.0095 (11) | 0.0132 (11) | 0.0039 (9) | 0.0037 (9) | 0.0026 (9) |
C8 | 0.0182 (13) | 0.0230 (13) | 0.0200 (13) | 0.0084 (11) | 0.0124 (10) | 0.0121 (11) |
C9 | 0.0138 (12) | 0.0234 (14) | 0.0222 (13) | 0.0050 (10) | 0.0113 (10) | 0.0100 (11) |
Se1—C3 | 1.890 (3) | C5—C6 | 1.321 (4) |
Se1—C1 | 1.906 (2) | C5—H5 | 0.9500 |
Se2—C4 | 1.890 (3) | C6—H6 | 0.9500 |
Se2—C1 | 1.900 (2) | Se5—C8 | 1.885 (3) |
Se3—C5 | 1.889 (3) | Se5—C7 | 1.904 (2) |
Se3—C2 | 1.898 (2) | Se6—C9 | 1.881 (3) |
Se4—C6 | 1.897 (3) | Se6—C7 | 1.910 (2) |
Se4—C2 | 1.906 (2) | C7—C7i | 1.333 (5) |
C1—C2 | 1.340 (3) | C8—C9 | 1.333 (4) |
C3—C4 | 1.326 (4) | C8—H8 | 0.9500 |
C3—H3 | 0.9500 | C9—H9 | 0.9500 |
C4—H4 | 0.9500 | ||
C3—Se1—C1 | 91.96 (11) | C6—C5—H5 | 120.1 |
C4—Se2—C1 | 92.24 (11) | Se3—C5—H5 | 120.1 |
C5—Se3—C2 | 91.21 (11) | C5—C6—Se4 | 118.6 (2) |
C6—Se4—C2 | 91.32 (11) | C5—C6—H6 | 120.7 |
C2—C1—Se2 | 122.7 (2) | Se4—C6—H6 | 120.7 |
C2—C1—Se1 | 122.79 (19) | C8—Se5—C7 | 93.10 (11) |
Se2—C1—Se1 | 114.48 (12) | C9—Se6—C7 | 93.04 (11) |
C1—C2—Se3 | 123.89 (19) | C7i—C7—Se5 | 123.4 (2) |
C1—C2—Se4 | 123.2 (2) | C7i—C7—Se6 | 122.3 (3) |
Se3—C2—Se4 | 112.90 (12) | Se5—C7—Se6 | 114.25 (12) |
C4—C3—Se1 | 119.9 (2) | C9—C8—Se5 | 119.7 (2) |
C4—C3—H3 | 120.0 | C9—C8—H8 | 120.2 |
Se1—C3—H3 | 120.0 | Se5—C8—H8 | 120.2 |
C3—C4—Se2 | 119.5 (2) | C8—C9—Se6 | 119.9 (2) |
C3—C4—H4 | 120.2 | C8—C9—H9 | 120.1 |
Se2—C4—H4 | 120.2 | Se6—C9—H9 | 120.1 |
C6—C5—Se3 | 119.9 (2) | ||
C4—Se2—C1—C2 | −166.8 (2) | Se1—C3—C4—Se2 | −0.3 (3) |
C4—Se2—C1—Se1 | 13.07 (14) | C1—Se2—C4—C3 | −7.9 (3) |
C3—Se1—C1—C2 | 166.7 (2) | C2—Se3—C5—C6 | 14.7 (2) |
C3—Se1—C1—Se2 | −13.14 (14) | Se3—C5—C6—Se4 | −0.1 (3) |
Se2—C1—C2—Se3 | 1.6 (3) | C2—Se4—C6—C5 | −14.5 (2) |
Se1—C1—C2—Se3 | −178.23 (12) | C8—Se5—C7—C7i | −178.7 (3) |
Se2—C1—C2—Se4 | 179.08 (12) | C8—Se5—C7—Se6 | 2.02 (14) |
Se1—C1—C2—Se4 | −0.8 (3) | C9—Se6—C7—C7i | 178.7 (3) |
C5—Se3—C2—C1 | 154.2 (2) | C9—Se6—C7—Se5 | −1.97 (14) |
C5—Se3—C2—Se4 | −23.44 (14) | C7—Se5—C8—C9 | −1.3 (2) |
C6—Se4—C2—C1 | −154.2 (2) | Se5—C8—C9—Se6 | 0.1 (3) |
C6—Se4—C2—Se3 | 23.46 (14) | C7—Se6—C9—C8 | 1.1 (2) |
C1—Se1—C3—C4 | 8.3 (3) |
Symmetry code: (i) −x, −y+1, −z+1. |