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
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.004 Å
- R factor = 0.020
- wR factor = 0.051
- Data-to-parameter ratio = 23.1
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR) is > 1.50 Tmin and Tmax reported: 0.170 0.262 Tmin and Tmax expected: 0.086 0.262 RR = 1.972 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_B Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.98
Alert level C PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 30 Ang. PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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. |
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