Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111049900/bm3112sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111049900/bm3112Iasup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111049900/bm3112Ibsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111049900/bm3112IIbsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111049900/bm3112IIIsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111049900/bm3112IVsup6.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111049900/bm3112Iasup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111049900/bm3112Ibsup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111049900/bm3112IIbsup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111049900/bm3112IIIsup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270111049900/bm3112IVsup11.cml |
CCDC references: 862244; 862245; 862246; 862247; 862248
All compounds were prepared according to literature methods by the reaction of Woollins' reagent with either the appropriate 1,2-diacylhydrazine [for (Ia), (Ib), (III) and (IV); Hua et al., 2009] or acylcarbohydrazide [for (IIb); Hua, Cordes et al., 2011]. X-ray quality crystals of all compounds were grown by the diffusion of hexane into a dichloromethane solution of the compound. Crystals of the two polymorphic forms of 2,5-diphenyl-1,3,4-selenadiazole, (Ia) and (Ib), were difficult to differentiate visually, except that the platelets of (Ia) tended to be thicker than those of (Ib). Crystals of (IIb) were likewise difficult to differentiate from those of the known polymorph (IIa) (Hua, Cordes et al., 2011), although those of (IIb) did tend to display a more intense orange colour.
C-bound H atoms were included in calculated positions (C—H = 0.98 Å for methyl H atoms and 0.95 Å for aryl H atoms) and refined as riding, with Uiso(H) = 1.2Ueq(C) for aryl H or 1.5Ueq(C) for methyl H. The structure of (IIb) shows signs of racemic twinning, the Flack (1983) parameter being 0.377 (19). This is complicated by the Friedel-pair coverage being lower than ideal, at 68%, which suggests that the Flack parameter in this case may be less meaningful than generally. In (III), a difference electron-density feature of 4.87 e %A-3 was located 1.37 Å from atom Se1, but this has no chemical significance.
For all compounds, data collection: CrystalClear (Rigaku, 2010); cell refinement: CrystalClear (Rigaku, 2010); data reduction: CrystalClear (Rigaku, 2010); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008). Molecular graphics: SHELXTL (Sheldrick, 2008) and OLEX (Dolomanov et al., 2003) for (Ia), (Ib), (IIb); SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2003) for (III), (IV). For all compounds, software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
C14H10N2Se | F(000) = 568 |
Mr = 285.20 | Dx = 1.670 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3915 reflections |
a = 13.036 (4) Å | θ = 1.6–28.4° |
b = 5.4650 (14) Å | µ = 3.29 mm−1 |
c = 16.274 (5) Å | T = 93 K |
β = 101.860 (7)° | Platelet, colourless |
V = 1134.6 (5) Å3 | 0.15 × 0.10 × 0.05 mm |
Z = 4 |
Rigaku Mercury CCD area-detector diffractometer | 2413 independent reflections |
Radiation source: rotating anode | 2081 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.037 |
Detector resolution: 14.7059 pixels mm-1 | θmax = 28.6°, θmin = 1.6° |
ω and ϕ scans | h = −16→15 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | k = −7→5 |
Tmin = 0.795, Tmax = 1.000 | l = −16→21 |
7425 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0205P)2 + 1.2418P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
2413 reflections | Δρmax = 1.25 e Å−3 |
155 parameters | Δρmin = −0.69 e Å−3 |
0 restraints | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0024 (6) |
C14H10N2Se | V = 1134.6 (5) Å3 |
Mr = 285.20 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.036 (4) Å | µ = 3.29 mm−1 |
b = 5.4650 (14) Å | T = 93 K |
c = 16.274 (5) Å | 0.15 × 0.10 × 0.05 mm |
β = 101.860 (7)° |
Rigaku Mercury CCD area-detector diffractometer | 2413 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | 2081 reflections with I > 2σ(I) |
Tmin = 0.795, Tmax = 1.000 | Rint = 0.037 |
7425 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.09 | Δρmax = 1.25 e Å−3 |
2413 reflections | Δρmin = −0.69 e Å−3 |
155 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. |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.91133 (2) | 0.13109 (5) | 0.293061 (16) | 0.02068 (14) | |
N4 | 0.82019 (19) | −0.2835 (4) | 0.33044 (14) | 0.0249 (6) | |
N3 | 0.91878 (19) | −0.2871 (4) | 0.38062 (14) | 0.0234 (5) | |
C5 | 0.7995 (2) | −0.0927 (5) | 0.28210 (17) | 0.0202 (6) | |
C21 | 0.6975 (2) | −0.0548 (5) | 0.22543 (16) | 0.0205 (6) | |
C26 | 0.6179 (2) | −0.2262 (5) | 0.22610 (18) | 0.0240 (6) | |
H26 | 0.6304 | −0.3625 | 0.2630 | 0.029* | |
C25 | 0.5210 (2) | −0.1981 (6) | 0.17321 (18) | 0.0278 (7) | |
H25 | 0.4672 | −0.3146 | 0.1744 | 0.033* | |
C24 | 0.5015 (2) | −0.0003 (5) | 0.11811 (18) | 0.0268 (7) | |
H24 | 0.4353 | 0.0173 | 0.0811 | 0.032* | |
C23 | 0.5801 (2) | 0.1705 (5) | 0.11809 (18) | 0.0249 (7) | |
H23 | 0.5673 | 0.3067 | 0.0811 | 0.030* | |
C22 | 0.6772 (2) | 0.1450 (5) | 0.17125 (18) | 0.0214 (6) | |
H22 | 0.7301 | 0.2641 | 0.1708 | 0.026* | |
C2 | 0.9772 (2) | −0.0997 (5) | 0.37245 (16) | 0.0190 (6) | |
C11 | 1.0842 (2) | −0.0686 (5) | 0.42239 (16) | 0.0189 (6) | |
C16 | 1.1249 (2) | −0.2410 (5) | 0.48439 (17) | 0.0219 (6) | |
H16 | 1.0839 | −0.3790 | 0.4929 | 0.026* | |
C15 | 1.2240 (2) | −0.2115 (5) | 0.53317 (18) | 0.0256 (7) | |
H15 | 1.2505 | −0.3285 | 0.5754 | 0.031* | |
C14 | 1.2853 (2) | −0.0119 (5) | 0.52103 (17) | 0.0246 (6) | |
H14 | 1.3536 | 0.0075 | 0.5546 | 0.029* | |
C13 | 1.2458 (2) | 0.1584 (5) | 0.45956 (18) | 0.0247 (7) | |
H13 | 1.2873 | 0.2953 | 0.4510 | 0.030* | |
C12 | 1.1461 (2) | 0.1305 (5) | 0.41050 (17) | 0.0212 (7) | |
H12 | 1.1199 | 0.2481 | 0.3685 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0254 (2) | 0.0157 (2) | 0.0217 (2) | −0.00100 (10) | 0.00638 (13) | 0.00346 (10) |
N4 | 0.0303 (14) | 0.0191 (13) | 0.0248 (13) | −0.0005 (11) | 0.0045 (10) | 0.0007 (11) |
N3 | 0.0283 (14) | 0.0169 (12) | 0.0258 (13) | −0.0009 (11) | 0.0073 (10) | 0.0017 (11) |
C5 | 0.0266 (16) | 0.0170 (14) | 0.0198 (14) | −0.0018 (12) | 0.0112 (12) | −0.0033 (12) |
C21 | 0.0247 (15) | 0.0188 (14) | 0.0203 (13) | 0.0003 (12) | 0.0101 (11) | −0.0035 (12) |
C26 | 0.0304 (17) | 0.0191 (15) | 0.0244 (14) | −0.0018 (13) | 0.0098 (13) | −0.0004 (13) |
C25 | 0.0308 (18) | 0.0258 (16) | 0.0291 (16) | −0.0045 (14) | 0.0113 (13) | −0.0037 (14) |
C24 | 0.0258 (16) | 0.0292 (17) | 0.0259 (15) | 0.0032 (13) | 0.0061 (12) | −0.0037 (13) |
C23 | 0.0278 (17) | 0.0224 (15) | 0.0261 (16) | 0.0065 (13) | 0.0096 (13) | 0.0039 (13) |
C22 | 0.0227 (16) | 0.0162 (15) | 0.0278 (16) | 0.0004 (11) | 0.0109 (13) | 0.0000 (12) |
C2 | 0.0287 (16) | 0.0146 (13) | 0.0163 (13) | 0.0029 (12) | 0.0105 (12) | −0.0017 (11) |
C11 | 0.0268 (15) | 0.0167 (13) | 0.0155 (13) | 0.0037 (12) | 0.0096 (11) | −0.0016 (12) |
C16 | 0.0261 (16) | 0.0178 (14) | 0.0242 (14) | 0.0027 (12) | 0.0111 (12) | 0.0033 (12) |
C15 | 0.0320 (17) | 0.0219 (16) | 0.0252 (15) | 0.0074 (13) | 0.0111 (13) | 0.0036 (13) |
C14 | 0.0251 (16) | 0.0271 (16) | 0.0217 (14) | 0.0002 (12) | 0.0051 (12) | −0.0033 (13) |
C13 | 0.0304 (18) | 0.0229 (15) | 0.0217 (15) | −0.0049 (12) | 0.0077 (13) | −0.0014 (12) |
C12 | 0.0318 (17) | 0.0180 (15) | 0.0146 (14) | 0.0026 (12) | 0.0066 (12) | 0.0028 (11) |
Se1—C2 | 1.882 (3) | C23—H23 | 0.9500 |
Se1—C5 | 1.883 (3) | C22—H22 | 0.9500 |
N4—C5 | 1.301 (3) | C2—C11 | 1.473 (4) |
N4—N3 | 1.374 (3) | C11—C12 | 1.391 (4) |
N3—C2 | 1.300 (3) | C11—C16 | 1.403 (4) |
C5—C21 | 1.469 (4) | C16—C15 | 1.380 (4) |
C21—C22 | 1.394 (4) | C16—H16 | 0.9500 |
C21—C26 | 1.400 (4) | C15—C14 | 1.390 (4) |
C26—C25 | 1.383 (4) | C15—H15 | 0.9500 |
C26—H26 | 0.9500 | C14—C13 | 1.386 (4) |
C25—C24 | 1.394 (4) | C14—H14 | 0.9500 |
C25—H25 | 0.9500 | C13—C12 | 1.387 (4) |
C24—C23 | 1.386 (4) | C13—H13 | 0.9500 |
C24—H24 | 0.9500 | C12—H12 | 0.9500 |
C23—C22 | 1.385 (4) | ||
C2—Se1—C5 | 82.25 (12) | C21—C22—H22 | 119.9 |
C5—N4—N3 | 115.1 (2) | N3—C2—C11 | 122.9 (2) |
C2—N3—N4 | 115.1 (2) | N3—C2—Se1 | 113.8 (2) |
N4—C5—C21 | 122.8 (3) | C11—C2—Se1 | 123.3 (2) |
N4—C5—Se1 | 113.8 (2) | C12—C11—C16 | 118.8 (3) |
C21—C5—Se1 | 123.5 (2) | C12—C11—C2 | 121.6 (2) |
C22—C21—C26 | 119.0 (3) | C16—C11—C2 | 119.6 (3) |
C22—C21—C5 | 122.5 (3) | C15—C16—C11 | 120.4 (3) |
C26—C21—C5 | 118.6 (3) | C15—C16—H16 | 119.8 |
C25—C26—C21 | 120.3 (3) | C11—C16—H16 | 119.8 |
C25—C26—H26 | 119.9 | C16—C15—C14 | 120.5 (3) |
C21—C26—H26 | 119.9 | C16—C15—H15 | 119.7 |
C26—C25—C24 | 120.6 (3) | C14—C15—H15 | 119.7 |
C26—C25—H25 | 119.7 | C13—C14—C15 | 119.4 (3) |
C24—C25—H25 | 119.7 | C13—C14—H14 | 120.3 |
C23—C24—C25 | 119.0 (3) | C15—C14—H14 | 120.3 |
C23—C24—H24 | 120.5 | C14—C13—C12 | 120.4 (3) |
C25—C24—H24 | 120.5 | C14—C13—H13 | 119.8 |
C22—C23—C24 | 120.9 (3) | C12—C13—H13 | 119.8 |
C22—C23—H23 | 119.6 | C13—C12—C11 | 120.5 (3) |
C24—C23—H23 | 119.6 | C13—C12—H12 | 119.7 |
C23—C22—C21 | 120.2 (3) | C11—C12—H12 | 119.7 |
C23—C22—H22 | 119.9 | ||
C5—N4—N3—C2 | −0.1 (3) | N4—N3—C2—C11 | 178.5 (2) |
N3—N4—C5—C21 | −178.8 (2) | N4—N3—C2—Se1 | −0.1 (3) |
N3—N4—C5—Se1 | 0.3 (3) | C5—Se1—C2—N3 | 0.2 (2) |
C2—Se1—C5—N4 | −0.2 (2) | C5—Se1—C2—C11 | −178.4 (2) |
C2—Se1—C5—C21 | 178.8 (2) | N3—C2—C11—C12 | 178.1 (2) |
N4—C5—C21—C22 | −177.3 (3) | Se1—C2—C11—C12 | −3.5 (4) |
Se1—C5—C21—C22 | 3.8 (4) | N3—C2—C11—C16 | −2.9 (4) |
N4—C5—C21—C26 | 2.7 (4) | Se1—C2—C11—C16 | 175.58 (19) |
Se1—C5—C21—C26 | −176.2 (2) | C12—C11—C16—C15 | 0.7 (4) |
C22—C21—C26—C25 | 0.5 (4) | C2—C11—C16—C15 | −178.4 (2) |
C5—C21—C26—C25 | −179.5 (3) | C11—C16—C15—C14 | −0.6 (4) |
C21—C26—C25—C24 | 0.5 (4) | C16—C15—C14—C13 | 0.3 (4) |
C26—C25—C24—C23 | −1.1 (4) | C15—C14—C13—C12 | 0.0 (4) |
C25—C24—C23—C22 | 0.6 (4) | C14—C13—C12—C11 | 0.1 (4) |
C24—C23—C22—C21 | 0.5 (4) | C16—C11—C12—C13 | −0.5 (4) |
C26—C21—C22—C23 | −1.0 (4) | C2—C11—C12—C13 | 178.6 (2) |
C5—C21—C22—C23 | 179.0 (3) |
C14H10N2Se | F(000) = 568 |
Mr = 285.20 | Dx = 1.744 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1743 reflections |
a = 26.763 (10) Å | θ = 1.6–28.5° |
b = 5.796 (2) Å | µ = 3.43 mm−1 |
c = 7.213 (3) Å | T = 93 K |
β = 103.885 (9)° | Platelet, colourless |
V = 1086.2 (7) Å3 | 0.25 × 0.20 × 0.01 mm |
Z = 4 |
Rigaku Mercury CCD area-detector diffractometer | 1149 independent reflections |
Radiation source: rotating anode | 1014 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.053 |
Detector resolution: 14.7059 pixels mm-1 | θmax = 28.5°, θmin = 1.6° |
ω and ϕ scans | h = −29→33 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | k = −7→6 |
Tmin = 0.490, Tmax = 1.000 | l = −8→8 |
3541 measured reflections |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0732P)2 + 8.2817P] where P = (Fo2 + 2Fc2)/3 |
1149 reflections | (Δ/σ)max < 0.001 |
78 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −1.14 e Å−3 |
C14H10N2Se | V = 1086.2 (7) Å3 |
Mr = 285.20 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 26.763 (10) Å | µ = 3.43 mm−1 |
b = 5.796 (2) Å | T = 93 K |
c = 7.213 (3) Å | 0.25 × 0.20 × 0.01 mm |
β = 103.885 (9)° |
Rigaku Mercury CCD area-detector diffractometer | 1149 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | 1014 reflections with I > 2σ(I) |
Tmin = 0.490, Tmax = 1.000 | Rint = 0.053 |
3541 measured reflections |
R[F2 > 2σ(F2)] = 0.066 | 0 restraints |
wR(F2) = 0.167 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.92 e Å−3 |
1149 reflections | Δρmin = −1.14 e Å−3 |
78 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. |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.0000 | 0.10447 (14) | 0.7500 | 0.0302 (4) | |
N3 | 0.02554 (18) | 0.5566 (9) | 0.7995 (7) | 0.0261 (11) | |
C2 | 0.0449 (2) | 0.3517 (10) | 0.8391 (8) | 0.0255 (12) | |
C11 | 0.0984 (2) | 0.3062 (10) | 0.9412 (8) | 0.0251 (12) | |
C16 | 0.1360 (2) | 0.4744 (11) | 0.9475 (8) | 0.0281 (13) | |
H16 | 0.1266 | 0.6183 | 0.8861 | 0.034* | |
C15 | 0.1858 (2) | 0.4374 (11) | 1.0392 (9) | 0.0291 (13) | |
H15 | 0.2109 | 0.5536 | 1.0411 | 0.035* | |
C14 | 0.1994 (2) | 0.2331 (12) | 1.1283 (9) | 0.0352 (15) | |
H14 | 0.2343 | 0.2080 | 1.1926 | 0.042* | |
C13 | 0.1646 (2) | 0.0640 (11) | 1.1282 (9) | 0.0303 (13) | |
H13 | 0.1751 | −0.0770 | 1.1931 | 0.036* | |
C12 | 0.1135 (2) | 0.0974 (9) | 1.0329 (9) | 0.0269 (13) | |
H12 | 0.0890 | −0.0217 | 1.0302 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0308 (6) | 0.0250 (5) | 0.0327 (6) | 0.000 | 0.0036 (4) | 0.000 |
N3 | 0.024 (3) | 0.028 (3) | 0.025 (3) | 0.0012 (19) | 0.0025 (19) | 0.000 (2) |
C2 | 0.022 (3) | 0.032 (3) | 0.022 (3) | −0.001 (2) | 0.004 (2) | −0.003 (2) |
C11 | 0.028 (3) | 0.021 (3) | 0.029 (3) | 0.000 (2) | 0.013 (2) | −0.001 (2) |
C16 | 0.032 (3) | 0.024 (3) | 0.028 (3) | −0.003 (2) | 0.008 (2) | 0.001 (3) |
C15 | 0.021 (3) | 0.032 (3) | 0.034 (3) | −0.006 (2) | 0.005 (2) | 0.003 (3) |
C14 | 0.027 (3) | 0.039 (4) | 0.039 (4) | 0.004 (3) | 0.006 (3) | −0.001 (3) |
C13 | 0.036 (4) | 0.029 (3) | 0.026 (3) | 0.007 (3) | 0.008 (3) | 0.003 (3) |
C12 | 0.029 (3) | 0.023 (3) | 0.029 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
Se1—C2 | 1.881 (6) | C16—H16 | 0.9500 |
Se1—C2i | 1.881 (6) | C15—C14 | 1.355 (9) |
N3—C2 | 1.300 (7) | C15—H15 | 0.9500 |
N3—N3i | 1.382 (9) | C14—C13 | 1.352 (9) |
C2—C11 | 1.470 (8) | C14—H14 | 0.9500 |
C11—C12 | 1.392 (8) | C13—C12 | 1.389 (9) |
C11—C16 | 1.394 (8) | C13—H13 | 0.9500 |
C16—C15 | 1.354 (8) | C12—H12 | 0.9500 |
C2—Se1—C2i | 80.7 (4) | C16—C15—H15 | 120.3 |
C2—N3—N3i | 113.9 (3) | C14—C15—H15 | 120.3 |
N3—C2—C11 | 124.2 (5) | C13—C14—C15 | 121.8 (6) |
N3—C2—Se1 | 115.7 (4) | C13—C14—H14 | 119.1 |
C11—C2—Se1 | 120.0 (4) | C15—C14—H14 | 119.1 |
C12—C11—C16 | 117.9 (5) | C14—C13—C12 | 119.7 (6) |
C12—C11—C2 | 122.1 (5) | C14—C13—H13 | 120.2 |
C16—C11—C2 | 120.0 (5) | C12—C13—H13 | 120.2 |
C15—C16—C11 | 121.5 (6) | C13—C12—C11 | 119.7 (6) |
C15—C16—H16 | 119.3 | C13—C12—H12 | 120.1 |
C11—C16—H16 | 119.3 | C11—C12—H12 | 120.1 |
C16—C15—C14 | 119.4 (6) | ||
N3i—N3—C2—C11 | 179.3 (5) | C12—C11—C16—C15 | 0.1 (9) |
N3i—N3—C2—Se1 | 1.1 (8) | C2—C11—C16—C15 | −179.5 (5) |
C2i—Se1—C2—N3 | −0.4 (3) | C11—C16—C15—C14 | −0.5 (9) |
C2i—Se1—C2—C11 | −178.7 (6) | C16—C15—C14—C13 | 0.1 (10) |
N3—C2—C11—C12 | 159.3 (6) | C15—C14—C13—C12 | 0.8 (10) |
Se1—C2—C11—C12 | −22.6 (7) | C14—C13—C12—C11 | −1.2 (9) |
N3—C2—C11—C16 | −21.1 (9) | C16—C11—C12—C13 | 0.7 (8) |
Se1—C2—C11—C16 | 157.0 (5) | C2—C11—C12—C13 | −179.7 (5) |
Symmetry code: (i) −x, y, −z+3/2. |
C10H6N2S2Se | F(000) = 584 |
Mr = 297.25 | Dx = 1.892 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3222 reflections |
a = 10.641 (5) Å | θ = 3.8–28.6° |
b = 5.134 (2) Å | µ = 3.96 mm−1 |
c = 19.096 (8) Å | T = 93 K |
V = 1043.4 (7) Å3 | Block, orange |
Z = 4 | 0.25 × 0.08 × 0.08 mm |
Rigaku Mercury CCD area-detector diffractometer | 2060 independent reflections |
Radiation source: rotating anode | 1704 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.083 |
Detector resolution: 14.7059 pixels mm-1 | θmax = 28.6°, θmin = 2.1° |
ω and ϕ scans | h = −13→12 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | k = −5→6 |
Tmin = 0.551, Tmax = 1.000 | l = −20→23 |
6487 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.0199P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max = 0.001 |
S = 1.12 | Δρmax = 1.08 e Å−3 |
2060 reflections | Δρmin = −0.67 e Å−3 |
138 parameters | Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0092 (14) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 874 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.377 (19) |
C10H6N2S2Se | V = 1043.4 (7) Å3 |
Mr = 297.25 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 10.641 (5) Å | µ = 3.96 mm−1 |
b = 5.134 (2) Å | T = 93 K |
c = 19.096 (8) Å | 0.25 × 0.08 × 0.08 mm |
Rigaku Mercury CCD area-detector diffractometer | 2060 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | 1704 reflections with I > 2σ(I) |
Tmin = 0.551, Tmax = 1.000 | Rint = 0.083 |
6487 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.116 | Δρmax = 1.08 e Å−3 |
S = 1.12 | Δρmin = −0.67 e Å−3 |
2060 reflections | Absolute structure: Flack (1983), with 874 Friedel pairs |
138 parameters | Absolute structure parameter: 0.377 (19) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.97218 (6) | 0.71715 (12) | 0.90178 (5) | 0.0303 (3) | |
S21 | 1.2387 (2) | 0.3484 (4) | 1.05778 (11) | 0.0377 (5) | |
S11 | 1.1823 (2) | 1.3291 (4) | 0.77777 (11) | 0.0400 (5) | |
N4 | 1.2154 (7) | 0.7314 (12) | 0.9380 (3) | 0.0343 (16) | |
N3 | 1.2041 (5) | 0.9148 (12) | 0.8873 (3) | 0.0334 (14) | |
C5 | 1.1126 (7) | 0.6082 (14) | 0.9529 (3) | 0.0289 (16) | |
C22 | 1.1073 (7) | 0.4086 (14) | 1.0068 (3) | 0.0296 (17) | |
C23 | 1.0089 (9) | 0.2461 (13) | 1.0249 (5) | 0.034 (2) | |
H23 | 0.9285 | 0.2507 | 1.0033 | 0.041* | |
C24 | 1.0418 (7) | 0.0731 (16) | 1.0791 (4) | 0.036 (2) | |
H24 | 0.9865 | −0.0554 | 1.0973 | 0.043* | |
C25 | 1.1613 (7) | 0.1097 (15) | 1.1025 (4) | 0.0378 (19) | |
H25 | 1.1977 | 0.0127 | 1.1397 | 0.045* | |
C2 | 1.0904 (6) | 0.9391 (13) | 0.8619 (3) | 0.0283 (16) | |
C12 | 1.0652 (7) | 1.1260 (14) | 0.8052 (4) | 0.0312 (16) | |
C13 | 0.9525 (8) | 1.1754 (16) | 0.7714 (4) | 0.0313 (19) | |
H13 | 0.8762 | 1.0855 | 0.7806 | 0.038* | |
C14 | 0.9657 (7) | 1.3778 (16) | 0.7213 (4) | 0.0339 (19) | |
H14 | 0.8988 | 1.4387 | 0.6927 | 0.041* | |
C15 | 1.0837 (7) | 1.4747 (15) | 0.7185 (4) | 0.044 (2) | |
H15 | 1.1091 | 1.6085 | 0.6872 | 0.052* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0280 (5) | 0.0308 (4) | 0.0323 (4) | 0.0002 (3) | −0.0015 (4) | 0.0017 (5) |
S21 | 0.0356 (12) | 0.0414 (13) | 0.0361 (11) | −0.0013 (10) | −0.0063 (9) | 0.0056 (8) |
S11 | 0.0365 (12) | 0.0356 (12) | 0.0478 (13) | −0.0010 (9) | 0.0022 (10) | 0.0072 (9) |
N4 | 0.030 (4) | 0.034 (4) | 0.039 (4) | 0.003 (3) | 0.000 (3) | 0.001 (3) |
N3 | 0.037 (4) | 0.031 (4) | 0.032 (4) | 0.005 (3) | −0.007 (3) | 0.004 (3) |
C5 | 0.027 (4) | 0.030 (5) | 0.030 (4) | 0.004 (3) | −0.002 (3) | −0.004 (3) |
C22 | 0.029 (4) | 0.035 (5) | 0.025 (4) | 0.004 (3) | 0.003 (3) | −0.003 (3) |
C23 | 0.033 (5) | 0.031 (5) | 0.039 (6) | −0.004 (3) | −0.016 (5) | −0.003 (3) |
C24 | 0.048 (5) | 0.028 (5) | 0.033 (5) | −0.010 (3) | 0.006 (3) | 0.003 (3) |
C25 | 0.040 (5) | 0.032 (5) | 0.042 (5) | −0.003 (4) | −0.002 (4) | 0.003 (3) |
C2 | 0.033 (4) | 0.028 (4) | 0.024 (3) | 0.001 (3) | 0.005 (3) | −0.006 (3) |
C12 | 0.037 (4) | 0.021 (4) | 0.036 (4) | −0.002 (3) | −0.005 (4) | −0.002 (3) |
C13 | 0.039 (5) | 0.025 (4) | 0.030 (5) | −0.004 (3) | 0.006 (4) | −0.001 (3) |
C14 | 0.042 (5) | 0.038 (5) | 0.022 (4) | 0.011 (4) | −0.007 (3) | −0.002 (3) |
C15 | 0.059 (6) | 0.032 (5) | 0.040 (5) | 0.010 (4) | 0.013 (4) | 0.003 (3) |
Se1—C2 | 1.861 (7) | C23—H23 | 0.9500 |
Se1—C5 | 1.870 (7) | C24—C25 | 1.361 (10) |
S21—C25 | 1.706 (8) | C24—H24 | 0.9500 |
S21—C22 | 1.732 (7) | C25—H25 | 0.9500 |
S11—C12 | 1.707 (8) | C2—C12 | 1.471 (9) |
S11—C15 | 1.714 (8) | C12—C13 | 1.386 (10) |
N4—C5 | 1.295 (10) | C13—C14 | 1.420 (12) |
N4—N3 | 1.357 (8) | C13—H13 | 0.9500 |
N3—C2 | 1.309 (8) | C14—C15 | 1.351 (10) |
C5—C22 | 1.454 (9) | C14—H14 | 0.9500 |
C22—C23 | 1.383 (11) | C15—H15 | 0.9500 |
C23—C24 | 1.408 (12) | ||
C2—Se1—C5 | 81.7 (3) | C24—C25—H25 | 123.6 |
C25—S21—C22 | 91.1 (4) | S21—C25—H25 | 123.6 |
C12—S11—C15 | 91.3 (4) | N3—C2—C12 | 120.2 (6) |
C5—N4—N3 | 114.9 (7) | N3—C2—Se1 | 114.5 (5) |
C2—N3—N4 | 114.4 (6) | C12—C2—Se1 | 125.3 (5) |
N4—C5—C22 | 122.1 (6) | C13—C12—C2 | 128.3 (7) |
N4—C5—Se1 | 114.5 (6) | C13—C12—S11 | 112.1 (6) |
C22—C5—Se1 | 123.3 (5) | C2—C12—S11 | 119.4 (5) |
C23—C22—C5 | 129.2 (7) | C12—C13—C14 | 111.2 (7) |
C23—C22—S21 | 111.3 (6) | C12—C13—H13 | 124.4 |
C5—C22—S21 | 119.5 (5) | C14—C13—H13 | 124.4 |
C22—C23—C24 | 112.1 (8) | C15—C14—C13 | 112.8 (7) |
C22—C23—H23 | 123.9 | C15—C14—H14 | 123.6 |
C24—C23—H23 | 123.9 | C13—C14—H14 | 123.6 |
C25—C24—C23 | 112.7 (7) | C14—C15—S11 | 112.5 (6) |
C25—C24—H24 | 123.6 | C14—C15—H15 | 123.8 |
C23—C24—H24 | 123.6 | S11—C15—H15 | 123.8 |
C24—C25—S21 | 112.7 (6) | ||
C5—N4—N3—C2 | 0.6 (9) | N4—N3—C2—C12 | −178.4 (6) |
N3—N4—C5—C22 | −178.9 (6) | N4—N3—C2—Se1 | 0.2 (8) |
N3—N4—C5—Se1 | −1.1 (8) | C5—Se1—C2—N3 | −0.6 (5) |
C2—Se1—C5—N4 | 0.9 (6) | C5—Se1—C2—C12 | 177.9 (6) |
C2—Se1—C5—C22 | 178.7 (6) | N3—C2—C12—C13 | 179.0 (7) |
N4—C5—C22—C23 | −174.2 (8) | Se1—C2—C12—C13 | 0.5 (11) |
Se1—C5—C22—C23 | 8.2 (11) | N3—C2—C12—S11 | −5.3 (9) |
N4—C5—C22—S21 | 5.0 (9) | Se1—C2—C12—S11 | 176.3 (4) |
Se1—C5—C22—S21 | −172.7 (4) | C15—S11—C12—C13 | −2.1 (6) |
C25—S21—C22—C23 | −0.2 (6) | C15—S11—C12—C2 | −178.5 (6) |
C25—S21—C22—C5 | −179.5 (6) | C2—C12—C13—C14 | 177.8 (7) |
C5—C22—C23—C24 | 178.4 (7) | S11—C12—C13—C14 | 1.7 (9) |
S21—C22—C23—C24 | −0.8 (9) | C12—C13—C14—C15 | −0.3 (10) |
C22—C23—C24—C25 | 1.7 (11) | C13—C14—C15—S11 | −1.3 (9) |
C23—C24—C25—S21 | −1.8 (9) | C12—S11—C15—C14 | 1.9 (6) |
C22—S21—C25—C24 | 1.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···N4i | 0.95 | 2.59 | 3.539 (12) | 177 |
Symmetry code: (i) x−1/2, −y+1, z. |
C14H9ClN2Se | F(000) = 632 |
Mr = 319.64 | Dx = 1.743 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4092 reflections |
a = 13.382 (5) Å | θ = 2.5–28.3° |
b = 5.5247 (18) Å | µ = 3.28 mm−1 |
c = 16.524 (5) Å | T = 93 K |
β = 94.528 (8)° | Platelet, colourless |
V = 1217.9 (7) Å3 | 0.12 × 0.07 × 0.01 mm |
Z = 4 |
Rigaku Mercury CCD area-detector diffractometer | 2513 independent reflections |
Radiation source: rotating anode | 2050 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.058 |
Detector resolution: 14.7059 pixels mm-1 | θmax = 28.4°, θmin = 2.5° |
ω and ϕ scans | h = −16→15 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | k = −7→4 |
Tmin = 0.500, Tmax = 1.000 | l = −15→21 |
7679 measured reflections |
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)] = 0.079 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.226 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1375P)2 + 2.8891P] where P = (Fo2 + 2Fc2)/3 |
2513 reflections | (Δ/σ)max = 0.001 |
163 parameters | Δρmax = 4.87 e Å−3 |
0 restraints | Δρmin = −1.07 e Å−3 |
C14H9ClN2Se | V = 1217.9 (7) Å3 |
Mr = 319.64 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.382 (5) Å | µ = 3.28 mm−1 |
b = 5.5247 (18) Å | T = 93 K |
c = 16.524 (5) Å | 0.12 × 0.07 × 0.01 mm |
β = 94.528 (8)° |
Rigaku Mercury CCD area-detector diffractometer | 2513 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | 2050 reflections with I > 2σ(I) |
Tmin = 0.500, Tmax = 1.000 | Rint = 0.058 |
7679 measured reflections |
R[F2 > 2σ(F2)] = 0.079 | 0 restraints |
wR(F2) = 0.226 | H-atom parameters constrained |
S = 1.06 | Δρmax = 4.87 e Å−3 |
2513 reflections | Δρmin = −1.07 e Å−3 |
163 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. A q-peak comprising 4.87 e- Å-3 was located 1.37 Å from Se1. |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.58869 (4) | 0.11522 (10) | 0.70232 (4) | 0.0261 (3) | |
Cl1 | 0.12692 (11) | 0.0260 (3) | 0.45025 (10) | 0.0373 (5) | |
N3 | 0.5849 (4) | −0.2964 (10) | 0.6164 (3) | 0.0257 (11) | |
N4 | 0.6764 (4) | −0.2978 (10) | 0.6608 (3) | 0.0309 (12) | |
C2 | 0.5288 (5) | −0.1089 (10) | 0.6283 (4) | 0.0260 (14) | |
C5 | 0.6941 (5) | −0.1088 (10) | 0.7076 (4) | 0.0242 (13) | |
C11 | 0.4298 (4) | −0.0772 (11) | 0.5848 (3) | 0.0214 (12) | |
C12 | 0.3720 (5) | 0.1270 (11) | 0.5985 (4) | 0.0284 (15) | |
H12 | 0.3969 | 0.2451 | 0.6368 | 0.034* | |
C13 | 0.2787 (5) | 0.1596 (12) | 0.5569 (4) | 0.0278 (14) | |
H13 | 0.2396 | 0.2994 | 0.5657 | 0.033* | |
C14 | 0.2441 (4) | −0.0182 (12) | 0.5021 (4) | 0.0307 (14) | |
C15 | 0.2990 (4) | −0.2191 (12) | 0.4869 (4) | 0.0272 (13) | |
H15 | 0.2745 | −0.3350 | 0.4477 | 0.033* | |
C16 | 0.3917 (5) | −0.2500 (11) | 0.5300 (4) | 0.0288 (13) | |
H16 | 0.4296 | −0.3921 | 0.5216 | 0.035* | |
C21 | 0.7874 (4) | −0.0788 (11) | 0.7598 (4) | 0.0242 (13) | |
C22 | 0.8030 (5) | 0.1245 (10) | 0.8100 (4) | 0.0268 (14) | |
H22 | 0.7539 | 0.2487 | 0.8096 | 0.032* | |
C23 | 0.8912 (5) | 0.1431 (12) | 0.8605 (4) | 0.0306 (15) | |
H23 | 0.9009 | 0.2825 | 0.8939 | 0.037* | |
C24 | 0.9644 (4) | −0.0303 (11) | 0.8642 (4) | 0.0253 (12) | |
H24 | 1.0231 | −0.0167 | 0.9001 | 0.030* | |
C25 | 0.9475 (5) | −0.2357 (13) | 0.8104 (4) | 0.0314 (14) | |
H25 | 0.9971 | −0.3583 | 0.8093 | 0.038* | |
C26 | 0.8609 (5) | −0.2551 (11) | 0.7612 (4) | 0.0265 (13) | |
H26 | 0.8509 | −0.3928 | 0.7271 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0309 (5) | 0.0185 (5) | 0.0290 (5) | 0.0025 (2) | 0.0037 (3) | −0.0032 (2) |
Cl1 | 0.0318 (8) | 0.0449 (11) | 0.0345 (10) | −0.0007 (7) | −0.0024 (6) | 0.0027 (7) |
N3 | 0.028 (2) | 0.021 (3) | 0.028 (3) | 0.006 (2) | 0.0023 (19) | −0.005 (2) |
N4 | 0.028 (3) | 0.027 (3) | 0.038 (3) | 0.001 (2) | 0.003 (2) | −0.003 (2) |
C2 | 0.035 (3) | 0.015 (3) | 0.029 (4) | −0.003 (2) | 0.008 (3) | 0.002 (2) |
C5 | 0.030 (3) | 0.017 (3) | 0.026 (3) | −0.003 (2) | 0.008 (2) | 0.000 (2) |
C11 | 0.026 (3) | 0.019 (3) | 0.020 (3) | −0.003 (2) | 0.009 (2) | 0.003 (2) |
C12 | 0.035 (3) | 0.022 (3) | 0.029 (4) | 0.002 (2) | 0.003 (3) | 0.001 (2) |
C13 | 0.035 (3) | 0.021 (3) | 0.028 (3) | 0.007 (3) | 0.008 (3) | 0.003 (3) |
C14 | 0.027 (3) | 0.032 (4) | 0.034 (4) | 0.000 (3) | 0.008 (2) | 0.007 (3) |
C15 | 0.028 (3) | 0.025 (3) | 0.028 (3) | −0.005 (2) | 0.004 (2) | −0.004 (3) |
C16 | 0.031 (3) | 0.020 (3) | 0.036 (3) | 0.002 (2) | 0.008 (2) | −0.006 (3) |
C21 | 0.025 (3) | 0.019 (3) | 0.029 (3) | −0.002 (2) | 0.009 (2) | 0.004 (2) |
C22 | 0.032 (3) | 0.020 (3) | 0.029 (4) | 0.000 (2) | 0.010 (3) | −0.003 (2) |
C23 | 0.036 (3) | 0.025 (3) | 0.031 (4) | −0.009 (3) | 0.005 (3) | −0.008 (3) |
C24 | 0.025 (3) | 0.025 (3) | 0.027 (3) | −0.001 (2) | 0.005 (2) | 0.005 (3) |
C25 | 0.033 (3) | 0.030 (4) | 0.032 (4) | 0.005 (3) | 0.004 (3) | 0.004 (3) |
C26 | 0.033 (3) | 0.020 (3) | 0.027 (3) | −0.001 (2) | 0.007 (2) | 0.002 (2) |
Se1—C5 | 1.874 (6) | C15—C16 | 1.391 (9) |
Se1—C2 | 1.875 (6) | C15—H15 | 0.9500 |
Cl1—C14 | 1.744 (7) | C16—H16 | 0.9500 |
N3—C2 | 1.304 (8) | C21—C26 | 1.383 (9) |
N3—N4 | 1.378 (7) | C21—C22 | 1.402 (8) |
N4—C5 | 1.309 (8) | C22—C23 | 1.394 (10) |
C2—C11 | 1.467 (9) | C22—H22 | 0.9500 |
C5—C21 | 1.470 (9) | C23—C24 | 1.368 (9) |
C11—C16 | 1.386 (8) | C23—H23 | 0.9500 |
C11—C12 | 1.396 (9) | C24—C25 | 1.448 (9) |
C12—C13 | 1.389 (9) | C24—H24 | 0.9500 |
C12—H12 | 0.9500 | C25—C26 | 1.366 (9) |
C13—C14 | 1.390 (10) | C25—H25 | 0.9500 |
C13—H13 | 0.9500 | C26—H26 | 0.9500 |
C14—C15 | 1.366 (9) | ||
C5—Se1—C2 | 82.9 (3) | C16—C15—H15 | 120.8 |
C2—N3—N4 | 115.0 (5) | C11—C16—C15 | 121.1 (6) |
C5—N4—N3 | 115.0 (5) | C11—C16—H16 | 119.4 |
N3—C2—C11 | 122.0 (6) | C15—C16—H16 | 119.4 |
N3—C2—Se1 | 113.7 (5) | C26—C21—C22 | 118.8 (6) |
C11—C2—Se1 | 124.3 (4) | C26—C21—C5 | 120.0 (6) |
N4—C5—C21 | 122.8 (5) | C22—C21—C5 | 121.2 (5) |
N4—C5—Se1 | 113.5 (5) | C23—C22—C21 | 119.5 (6) |
C21—C5—Se1 | 123.7 (4) | C23—C22—H22 | 120.2 |
C16—C11—C12 | 118.9 (6) | C21—C22—H22 | 120.2 |
C16—C11—C2 | 120.6 (5) | C24—C23—C22 | 122.9 (6) |
C12—C11—C2 | 120.5 (6) | C24—C23—H23 | 118.5 |
C13—C12—C11 | 120.8 (6) | C22—C23—H23 | 118.5 |
C13—C12—H12 | 119.6 | C23—C24—C25 | 116.4 (6) |
C11—C12—H12 | 119.6 | C23—C24—H24 | 121.8 |
C12—C13—C14 | 118.1 (6) | C25—C24—H24 | 121.8 |
C12—C13—H13 | 121.0 | C26—C25—C24 | 120.7 (6) |
C14—C13—H13 | 121.0 | C26—C25—H25 | 119.6 |
C15—C14—C13 | 122.6 (6) | C24—C25—H25 | 119.6 |
C15—C14—Cl1 | 119.9 (5) | C25—C26—C21 | 121.5 (6) |
C13—C14—Cl1 | 117.5 (5) | C25—C26—H26 | 119.2 |
C14—C15—C16 | 118.4 (6) | C21—C26—H26 | 119.2 |
C14—C15—H15 | 120.8 | ||
C2—N3—N4—C5 | −1.0 (8) | C13—C14—C15—C16 | 2.2 (10) |
N4—N3—C2—C11 | 179.0 (5) | Cl1—C14—C15—C16 | −179.3 (5) |
N4—N3—C2—Se1 | 1.0 (7) | C12—C11—C16—C15 | 2.1 (9) |
C5—Se1—C2—N3 | −0.6 (5) | C2—C11—C16—C15 | −178.4 (5) |
C5—Se1—C2—C11 | −178.5 (5) | C14—C15—C16—C11 | −2.6 (9) |
N3—N4—C5—C21 | 179.7 (5) | N4—C5—C21—C26 | −0.3 (9) |
N3—N4—C5—Se1 | 0.5 (7) | Se1—C5—C21—C26 | 178.9 (5) |
C2—Se1—C5—N4 | 0.1 (5) | N4—C5—C21—C22 | −179.1 (6) |
C2—Se1—C5—C21 | −179.2 (5) | Se1—C5—C21—C22 | 0.1 (8) |
N3—C2—C11—C16 | 1.1 (9) | C26—C21—C22—C23 | −0.7 (9) |
Se1—C2—C11—C16 | 178.9 (5) | C5—C21—C22—C23 | 178.1 (6) |
N3—C2—C11—C12 | −179.4 (6) | C21—C22—C23—C24 | −0.4 (10) |
Se1—C2—C11—C12 | −1.6 (8) | C22—C23—C24—C25 | 1.8 (10) |
C16—C11—C12—C13 | −1.2 (9) | C23—C24—C25—C26 | −2.1 (9) |
C2—C11—C12—C13 | 179.3 (6) | C24—C25—C26—C21 | 1.1 (9) |
C11—C12—C13—C14 | 0.8 (10) | C22—C21—C26—C25 | 0.4 (9) |
C12—C13—C14—C15 | −1.3 (10) | C5—C21—C26—C25 | −178.4 (6) |
C12—C13—C14—Cl1 | −179.8 (5) |
C13H10N2OSe | F(000) = 1152 |
Mr = 289.19 | Dx = 1.624 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7011 reflections |
a = 8.5036 (15) Å | θ = 2.4–28.1° |
b = 25.210 (5) Å | µ = 3.16 mm−1 |
c = 11.116 (2) Å | T = 93 K |
β = 96.814 (5)° | Platelet, colourless |
V = 2366.2 (8) Å3 | 0.30 × 0.20 × 0.04 mm |
Z = 8 |
Rigaku Mercury CCD area-detector diffractometer | 4865 independent reflections |
Radiation source: rotating anode | 3778 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.055 |
Detector resolution: 14.7059 pixels mm-1 | θmax = 28.4°, θmin = 2.4° |
ω and ϕ scans | h = −8→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | k = −30→30 |
Tmin = 0.558, Tmax = 1.000 | l = −8→13 |
15690 measured reflections |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0627P)2 + 3.0274P] where P = (Fo2 + 2Fc2)/3 |
4865 reflections | (Δ/σ)max < 0.001 |
309 parameters | Δρmax = 1.35 e Å−3 |
0 restraints | Δρmin = −1.03 e Å−3 |
C13H10N2OSe | V = 2366.2 (8) Å3 |
Mr = 289.19 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.5036 (15) Å | µ = 3.16 mm−1 |
b = 25.210 (5) Å | T = 93 K |
c = 11.116 (2) Å | 0.30 × 0.20 × 0.04 mm |
β = 96.814 (5)° |
Rigaku Mercury CCD area-detector diffractometer | 4865 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2010) | 3778 reflections with I > 2σ(I) |
Tmin = 0.558, Tmax = 1.000 | Rint = 0.055 |
15690 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 1.07 | Δρmax = 1.35 e Å−3 |
4865 reflections | Δρmin = −1.03 e Å−3 |
309 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. |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.95776 (5) | 0.609805 (19) | 0.54769 (5) | 0.03479 (17) | |
Se31 | 0.41752 (5) | 0.571510 (18) | 0.69908 (4) | 0.03316 (17) | |
O11 | 0.9742 (4) | 0.71563 (15) | 0.3949 (4) | 0.0497 (10) | |
O41 | 0.4615 (5) | 0.67205 (18) | 0.5440 (4) | 0.0678 (13) | |
N4 | 0.6889 (4) | 0.56170 (15) | 0.4536 (4) | 0.0306 (9) | |
N3 | 0.6937 (4) | 0.60813 (15) | 0.3890 (4) | 0.0324 (9) | |
N34 | 0.2462 (5) | 0.60326 (16) | 0.8742 (4) | 0.0372 (10) | |
N33 | 0.2606 (5) | 0.64772 (16) | 0.8048 (4) | 0.0384 (10) | |
C5 | 0.8087 (5) | 0.55386 (18) | 0.5365 (4) | 0.0286 (10) | |
C2 | 0.8173 (5) | 0.63757 (19) | 0.4200 (4) | 0.0304 (10) | |
C21 | 0.8273 (5) | 0.50612 (17) | 0.6113 (4) | 0.0268 (9) | |
C26 | 0.6987 (5) | 0.47135 (18) | 0.6129 (4) | 0.0310 (10) | |
H26 | 0.6004 | 0.4794 | 0.5666 | 0.037* | |
C25 | 0.7142 (5) | 0.42556 (18) | 0.6815 (4) | 0.0308 (10) | |
H25 | 0.6254 | 0.4027 | 0.6817 | 0.037* | |
C24 | 0.8558 (5) | 0.4119 (2) | 0.7503 (4) | 0.0323 (10) | |
C23 | 0.9839 (5) | 0.4469 (2) | 0.7475 (4) | 0.0331 (10) | |
H23 | 1.0825 | 0.4388 | 0.7934 | 0.040* | |
C22 | 0.9694 (5) | 0.49260 (19) | 0.6792 (4) | 0.0311 (10) | |
H22 | 1.0584 | 0.5153 | 0.6786 | 0.037* | |
C27 | 0.8695 (6) | 0.36290 (19) | 0.8269 (5) | 0.0377 (11) | |
H27A | 0.8035 | 0.3348 | 0.7863 | 0.057* | |
H27B | 0.8338 | 0.3706 | 0.9057 | 0.057* | |
H27C | 0.9802 | 0.3512 | 0.8387 | 0.057* | |
C12 | 0.8435 (6) | 0.68595 (18) | 0.3572 (5) | 0.0356 (11) | |
C13 | 0.7610 (6) | 0.7077 (2) | 0.2594 (5) | 0.0389 (12) | |
H13 | 0.6661 | 0.6946 | 0.2158 | 0.047* | |
C14 | 0.8455 (8) | 0.7547 (2) | 0.2340 (6) | 0.0548 (15) | |
H14 | 0.8167 | 0.7792 | 0.1701 | 0.066* | |
C15 | 0.9705 (8) | 0.7578 (2) | 0.3158 (6) | 0.0567 (16) | |
H15 | 1.0474 | 0.7853 | 0.3198 | 0.068* | |
C35 | 0.3168 (5) | 0.56102 (18) | 0.8394 (4) | 0.0292 (10) | |
C32 | 0.3422 (5) | 0.64067 (18) | 0.7134 (4) | 0.0324 (10) | |
C51 | 0.3128 (5) | 0.50983 (18) | 0.9003 (4) | 0.0297 (10) | |
C56 | 0.2204 (5) | 0.50328 (19) | 0.9959 (4) | 0.0343 (11) | |
H56 | 0.1633 | 0.5325 | 1.0228 | 0.041* | |
C55 | 0.2123 (5) | 0.4544 (2) | 1.0509 (4) | 0.0369 (11) | |
H55 | 0.1489 | 0.4505 | 1.1152 | 0.044* | |
C54 | 0.2948 (5) | 0.4107 (2) | 1.0144 (4) | 0.0330 (11) | |
C53 | 0.3882 (5) | 0.41835 (19) | 0.9207 (4) | 0.0343 (11) | |
H53 | 0.4478 | 0.3894 | 0.8956 | 0.041* | |
C52 | 0.3967 (5) | 0.46653 (18) | 0.8636 (4) | 0.0309 (10) | |
H52 | 0.4599 | 0.4702 | 0.7991 | 0.037* | |
C57 | 0.2820 (6) | 0.3572 (2) | 1.0735 (5) | 0.0440 (13) | |
H57A | 0.3843 | 0.3390 | 1.0783 | 0.066* | |
H57B | 0.2011 | 0.3359 | 1.0253 | 0.066* | |
H57C | 0.2522 | 0.3620 | 1.1553 | 0.066* | |
C42 | 0.3657 (5) | 0.68200 (19) | 0.6294 (5) | 0.0361 (11) | |
C43 | 0.3075 (6) | 0.73151 (19) | 0.6209 (5) | 0.0462 (14) | |
H43 | 0.2410 | 0.7479 | 0.6729 | 0.055* | |
C44 | 0.3665 (7) | 0.7546 (3) | 0.5173 (6) | 0.0624 (18) | |
H44 | 0.3451 | 0.7891 | 0.4850 | 0.075* | |
C45 | 0.4572 (8) | 0.7176 (3) | 0.4759 (6) | 0.071 (2) | |
H45 | 0.5127 | 0.7220 | 0.4073 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0310 (3) | 0.0369 (3) | 0.0357 (3) | −0.00673 (18) | 0.0011 (2) | −0.0054 (2) |
Se31 | 0.0366 (3) | 0.0307 (3) | 0.0337 (3) | 0.00295 (18) | 0.0105 (2) | −0.0041 (2) |
O11 | 0.046 (2) | 0.046 (2) | 0.058 (3) | −0.0118 (17) | 0.0119 (18) | −0.0026 (19) |
O41 | 0.075 (3) | 0.058 (3) | 0.080 (3) | 0.000 (2) | 0.043 (3) | 0.005 (2) |
N4 | 0.028 (2) | 0.034 (2) | 0.030 (2) | −0.0026 (15) | 0.0064 (16) | −0.0003 (18) |
N3 | 0.031 (2) | 0.034 (2) | 0.032 (2) | −0.0020 (16) | 0.0049 (16) | −0.0014 (18) |
N34 | 0.042 (2) | 0.036 (2) | 0.033 (2) | 0.0092 (17) | 0.0061 (18) | −0.0014 (19) |
N33 | 0.046 (2) | 0.036 (2) | 0.033 (2) | 0.0094 (18) | 0.0073 (19) | −0.0045 (19) |
C5 | 0.023 (2) | 0.038 (3) | 0.025 (2) | 0.0004 (18) | 0.0060 (17) | −0.006 (2) |
C2 | 0.026 (2) | 0.035 (2) | 0.031 (3) | −0.0021 (18) | 0.0073 (18) | −0.006 (2) |
C21 | 0.026 (2) | 0.033 (2) | 0.021 (2) | −0.0016 (17) | 0.0056 (17) | −0.007 (2) |
C26 | 0.026 (2) | 0.037 (3) | 0.030 (3) | −0.0029 (18) | 0.0059 (18) | −0.005 (2) |
C25 | 0.025 (2) | 0.036 (3) | 0.033 (3) | −0.0040 (18) | 0.0084 (19) | −0.005 (2) |
C24 | 0.032 (3) | 0.040 (3) | 0.027 (3) | 0.004 (2) | 0.0080 (19) | −0.005 (2) |
C23 | 0.028 (2) | 0.043 (3) | 0.029 (3) | 0.002 (2) | 0.0006 (18) | −0.005 (2) |
C22 | 0.028 (2) | 0.039 (3) | 0.026 (2) | −0.0021 (19) | 0.0016 (18) | −0.006 (2) |
C27 | 0.042 (3) | 0.036 (3) | 0.037 (3) | 0.001 (2) | 0.009 (2) | 0.000 (2) |
C12 | 0.040 (3) | 0.028 (2) | 0.041 (3) | −0.0066 (19) | 0.016 (2) | −0.008 (2) |
C13 | 0.036 (3) | 0.041 (3) | 0.040 (3) | 0.001 (2) | 0.004 (2) | −0.003 (2) |
C14 | 0.073 (4) | 0.040 (3) | 0.055 (4) | 0.010 (3) | 0.026 (3) | 0.009 (3) |
C15 | 0.077 (4) | 0.032 (3) | 0.068 (4) | −0.009 (3) | 0.036 (4) | 0.001 (3) |
C35 | 0.029 (2) | 0.031 (2) | 0.026 (2) | 0.0024 (18) | −0.0024 (18) | −0.008 (2) |
C32 | 0.030 (2) | 0.032 (3) | 0.033 (3) | 0.0024 (18) | −0.0024 (19) | −0.003 (2) |
C51 | 0.028 (2) | 0.034 (2) | 0.027 (2) | 0.0026 (18) | −0.0025 (18) | −0.005 (2) |
C56 | 0.036 (3) | 0.039 (3) | 0.029 (3) | −0.001 (2) | 0.006 (2) | −0.007 (2) |
C55 | 0.033 (3) | 0.048 (3) | 0.029 (3) | −0.003 (2) | 0.0031 (19) | −0.001 (2) |
C54 | 0.031 (3) | 0.039 (3) | 0.028 (3) | −0.003 (2) | −0.0013 (19) | 0.001 (2) |
C53 | 0.030 (3) | 0.036 (3) | 0.036 (3) | 0.0029 (19) | 0.002 (2) | −0.006 (2) |
C52 | 0.027 (2) | 0.037 (3) | 0.030 (3) | 0.0001 (18) | 0.0064 (18) | −0.002 (2) |
C57 | 0.047 (3) | 0.046 (3) | 0.038 (3) | −0.007 (2) | 0.002 (2) | 0.005 (3) |
C42 | 0.033 (3) | 0.036 (3) | 0.040 (3) | −0.0008 (19) | 0.004 (2) | −0.005 (2) |
C43 | 0.063 (4) | 0.027 (3) | 0.054 (4) | 0.009 (2) | 0.032 (3) | 0.012 (3) |
C44 | 0.056 (4) | 0.053 (4) | 0.079 (5) | 0.000 (3) | 0.009 (3) | 0.033 (4) |
C45 | 0.073 (5) | 0.092 (6) | 0.053 (4) | −0.018 (4) | 0.031 (3) | −0.001 (4) |
Se1—C2 | 1.879 (5) | C27—H27C | 0.9800 |
Se1—C5 | 1.890 (4) | C12—C13 | 1.339 (7) |
Se31—C32 | 1.871 (5) | C13—C14 | 1.432 (7) |
Se31—C35 | 1.885 (5) | C13—H13 | 0.9500 |
O11—C12 | 1.363 (6) | C14—C15 | 1.317 (9) |
O11—C15 | 1.378 (7) | C14—H14 | 0.9500 |
O41—C42 | 1.346 (6) | C15—H15 | 0.9500 |
O41—C45 | 1.372 (8) | C35—C51 | 1.460 (6) |
N4—C5 | 1.305 (6) | C32—C42 | 1.429 (7) |
N4—N3 | 1.377 (5) | C51—C52 | 1.392 (6) |
N3—C2 | 1.299 (6) | C51—C56 | 1.405 (6) |
N34—C35 | 1.303 (6) | C56—C55 | 1.381 (7) |
N34—N33 | 1.374 (6) | C56—H56 | 0.9500 |
N33—C32 | 1.309 (6) | C55—C54 | 1.392 (7) |
C5—C21 | 1.461 (6) | C55—H55 | 0.9500 |
C2—C12 | 1.436 (7) | C54—C53 | 1.396 (7) |
C21—C22 | 1.389 (6) | C54—C57 | 1.511 (7) |
C21—C26 | 1.403 (6) | C53—C52 | 1.377 (6) |
C26—C25 | 1.381 (6) | C53—H53 | 0.9500 |
C26—H26 | 0.9500 | C52—H52 | 0.9500 |
C25—C24 | 1.391 (6) | C57—H57A | 0.9800 |
C25—H25 | 0.9500 | C57—H57B | 0.9800 |
C24—C23 | 1.405 (7) | C57—H57C | 0.9800 |
C24—C27 | 1.497 (7) | C42—C43 | 1.342 (6) |
C23—C22 | 1.378 (7) | C43—C44 | 1.433 (8) |
C23—H23 | 0.9500 | C43—H43 | 0.9500 |
C22—H22 | 0.9500 | C44—C45 | 1.328 (9) |
C27—H27A | 0.9800 | C44—H44 | 0.9500 |
C27—H27B | 0.9800 | C45—H45 | 0.9500 |
C2—Se1—C5 | 82.36 (19) | C13—C14—H14 | 126.4 |
C32—Se31—C35 | 82.3 (2) | C14—C15—O11 | 110.5 (5) |
C12—O11—C15 | 105.8 (4) | C14—C15—H15 | 124.8 |
C42—O41—C45 | 104.7 (5) | O11—C15—H15 | 124.8 |
C5—N4—N3 | 115.4 (4) | N34—C35—C51 | 123.2 (4) |
C2—N3—N4 | 114.8 (4) | N34—C35—Se31 | 113.7 (4) |
C35—N34—N33 | 115.2 (4) | C51—C35—Se31 | 123.1 (3) |
C32—N33—N34 | 114.5 (4) | N33—C32—C42 | 122.5 (4) |
N4—C5—C21 | 123.3 (4) | N33—C32—Se31 | 114.3 (4) |
N4—C5—Se1 | 113.2 (3) | C42—C32—Se31 | 123.2 (4) |
C21—C5—Se1 | 123.4 (3) | C52—C51—C56 | 118.8 (4) |
N3—C2—C12 | 121.6 (4) | C52—C51—C35 | 121.1 (4) |
N3—C2—Se1 | 114.2 (4) | C56—C51—C35 | 120.1 (4) |
C12—C2—Se1 | 124.2 (3) | C55—C56—C51 | 120.1 (4) |
C22—C21—C26 | 118.0 (4) | C55—C56—H56 | 119.9 |
C22—C21—C5 | 122.7 (4) | C51—C56—H56 | 119.9 |
C26—C21—C5 | 119.3 (4) | C56—C55—C54 | 121.5 (5) |
C25—C26—C21 | 120.4 (4) | C56—C55—H55 | 119.2 |
C25—C26—H26 | 119.8 | C54—C55—H55 | 119.2 |
C21—C26—H26 | 119.8 | C55—C54—C53 | 117.4 (5) |
C26—C25—C24 | 122.0 (4) | C55—C54—C57 | 121.0 (4) |
C26—C25—H25 | 119.0 | C53—C54—C57 | 121.6 (5) |
C24—C25—H25 | 119.0 | C52—C53—C54 | 122.1 (4) |
C25—C24—C23 | 117.1 (4) | C52—C53—H53 | 118.9 |
C25—C24—C27 | 121.4 (4) | C54—C53—H53 | 118.9 |
C23—C24—C27 | 121.5 (4) | C53—C52—C51 | 120.0 (4) |
C22—C23—C24 | 121.2 (4) | C53—C52—H52 | 120.0 |
C22—C23—H23 | 119.4 | C51—C52—H52 | 120.0 |
C24—C23—H23 | 119.4 | C54—C57—H57A | 109.5 |
C23—C22—C21 | 121.3 (4) | C54—C57—H57B | 109.5 |
C23—C22—H22 | 119.3 | H57A—C57—H57B | 109.5 |
C21—C22—H22 | 119.3 | C54—C57—H57C | 109.5 |
C24—C27—H27A | 109.5 | H57A—C57—H57C | 109.5 |
C24—C27—H27B | 109.5 | H57B—C57—H57C | 109.5 |
H27A—C27—H27B | 109.5 | C43—C42—O41 | 111.9 (5) |
C24—C27—H27C | 109.5 | C43—C42—C32 | 130.1 (5) |
H27A—C27—H27C | 109.5 | O41—C42—C32 | 117.9 (4) |
H27B—C27—H27C | 109.5 | C42—C43—C44 | 105.8 (5) |
C13—C12—O11 | 110.7 (4) | C42—C43—H43 | 127.1 |
C13—C12—C2 | 130.2 (5) | C44—C43—H43 | 127.1 |
O11—C12—C2 | 119.0 (5) | C45—C44—C43 | 105.4 (5) |
C12—C13—C14 | 105.8 (5) | C45—C44—H44 | 127.3 |
C12—C13—H13 | 127.1 | C43—C44—H44 | 127.3 |
C14—C13—H13 | 127.1 | C44—C45—O41 | 112.1 (6) |
C15—C14—C13 | 107.2 (5) | C44—C45—H45 | 124.0 |
C15—C14—H14 | 126.4 | O41—C45—H45 | 124.0 |
C5—N4—N3—C2 | 0.0 (6) | C12—O11—C15—C14 | 0.0 (6) |
C35—N34—N33—C32 | 0.6 (6) | N33—N34—C35—C51 | −179.0 (4) |
N3—N4—C5—C21 | −177.8 (4) | N33—N34—C35—Se31 | −1.4 (5) |
N3—N4—C5—Se1 | 1.0 (5) | C32—Se31—C35—N34 | 1.3 (3) |
C2—Se1—C5—N4 | −1.2 (3) | C32—Se31—C35—C51 | 178.9 (4) |
C2—Se1—C5—C21 | 177.7 (4) | N34—N33—C32—C42 | 178.2 (4) |
N4—N3—C2—C12 | 176.9 (4) | N34—N33—C32—Se31 | 0.5 (5) |
N4—N3—C2—Se1 | −0.9 (5) | C35—Se31—C32—N33 | −1.0 (4) |
C5—Se1—C2—N3 | 1.2 (3) | C35—Se31—C32—C42 | −178.6 (4) |
C5—Se1—C2—C12 | −176.6 (4) | N34—C35—C51—C52 | −176.7 (4) |
N4—C5—C21—C22 | 165.2 (4) | Se31—C35—C51—C52 | 6.0 (6) |
Se1—C5—C21—C22 | −13.5 (6) | N34—C35—C51—C56 | 4.7 (7) |
N4—C5—C21—C26 | −12.9 (6) | Se31—C35—C51—C56 | −172.6 (3) |
Se1—C5—C21—C26 | 168.4 (3) | C52—C51—C56—C55 | −0.8 (6) |
C22—C21—C26—C25 | 0.8 (6) | C35—C51—C56—C55 | 177.8 (4) |
C5—C21—C26—C25 | 179.0 (4) | C51—C56—C55—C54 | 0.3 (7) |
C21—C26—C25—C24 | −0.4 (7) | C56—C55—C54—C53 | 0.9 (7) |
C26—C25—C24—C23 | 0.0 (7) | C56—C55—C54—C57 | −178.6 (4) |
C26—C25—C24—C27 | 178.3 (4) | C55—C54—C53—C52 | −1.6 (7) |
C25—C24—C23—C22 | 0.0 (7) | C57—C54—C53—C52 | 177.9 (4) |
C27—C24—C23—C22 | −178.3 (4) | C54—C53—C52—C51 | 1.2 (7) |
C24—C23—C22—C21 | 0.4 (7) | C56—C51—C52—C53 | 0.0 (6) |
C26—C21—C22—C23 | −0.8 (7) | C35—C51—C52—C53 | −178.5 (4) |
C5—C21—C22—C23 | −179.0 (4) | C45—O41—C42—C43 | −2.3 (7) |
C15—O11—C12—C13 | 0.2 (6) | C45—O41—C42—C32 | 178.2 (5) |
C15—O11—C12—C2 | 177.8 (4) | N33—C32—C42—C43 | −4.3 (8) |
N3—C2—C12—C13 | −3.9 (8) | Se31—C32—C42—C43 | 173.1 (5) |
Se1—C2—C12—C13 | 173.7 (4) | N33—C32—C42—O41 | 175.0 (5) |
N3—C2—C12—O11 | 179.1 (4) | Se31—C32—C42—O41 | −7.6 (6) |
Se1—C2—C12—O11 | −3.3 (6) | O41—C42—C43—C44 | 2.6 (7) |
O11—C12—C13—C14 | −0.4 (6) | C32—C42—C43—C44 | −178.1 (5) |
C2—C12—C13—C14 | −177.6 (5) | C42—C43—C44—C45 | −1.7 (7) |
C12—C13—C14—C15 | 0.4 (6) | C43—C44—C45—O41 | 0.3 (8) |
C13—C14—C15—O11 | −0.3 (6) | C42—O41—C45—C44 | 1.2 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N33i | 0.95 | 2.50 | 3.441 (7) | 172 |
C44—H44···N33ii | 0.95 | 2.59 | 3.457 (7) | 151 |
Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x, −y+3/2, z−1/2. |
Experimental details
(Ia) | (Ib) | (IIb) | (III) | |
Crystal data | ||||
Chemical formula | C14H10N2Se | C14H10N2Se | C10H6N2S2Se | C14H9ClN2Se |
Mr | 285.20 | 285.20 | 297.25 | 319.64 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, C2/c | Orthorhombic, Pca21 | Monoclinic, P21/c |
Temperature (K) | 93 | 93 | 93 | 93 |
a, b, c (Å) | 13.036 (4), 5.4650 (14), 16.274 (5) | 26.763 (10), 5.796 (2), 7.213 (3) | 10.641 (5), 5.134 (2), 19.096 (8) | 13.382 (5), 5.5247 (18), 16.524 (5) |
α, β, γ (°) | 90, 101.860 (7), 90 | 90, 103.885 (9), 90 | 90, 90, 90 | 90, 94.528 (8), 90 |
V (Å3) | 1134.6 (5) | 1086.2 (7) | 1043.4 (7) | 1217.9 (7) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 3.29 | 3.43 | 3.96 | 3.28 |
Crystal size (mm) | 0.15 × 0.10 × 0.05 | 0.25 × 0.20 × 0.01 | 0.25 × 0.08 × 0.08 | 0.12 × 0.07 × 0.01 |
Data collection | ||||
Diffractometer | Rigaku Mercury CCD area-detector diffractometer | Rigaku Mercury CCD area-detector diffractometer | Rigaku Mercury CCD area-detector diffractometer | Rigaku Mercury CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2010) | Multi-scan (CrystalClear; Rigaku, 2010) | Multi-scan (CrystalClear; Rigaku, 2010) | Multi-scan (CrystalClear; Rigaku, 2010) |
Tmin, Tmax | 0.795, 1.000 | 0.490, 1.000 | 0.551, 1.000 | 0.500, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7425, 2413, 2081 | 3541, 1149, 1014 | 6487, 2060, 1704 | 7679, 2513, 2050 |
Rint | 0.037 | 0.053 | 0.083 | 0.058 |
(sin θ/λ)max (Å−1) | 0.672 | 0.671 | 0.673 | 0.668 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.081, 1.09 | 0.066, 0.167, 1.11 | 0.054, 0.116, 1.12 | 0.079, 0.226, 1.06 |
No. of reflections | 2413 | 1149 | 2060 | 2513 |
No. of parameters | 155 | 78 | 138 | 163 |
No. of restraints | 0 | 0 | 1 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.25, −0.69 | 0.92, −1.14 | 1.08, −0.67 | 4.87, −1.07 |
Absolute structure | ? | ? | Flack (1983), with 874 Friedel pairs | ? |
Absolute structure parameter | ? | ? | 0.377 (19) | ? |
(IV) | |
Crystal data | |
Chemical formula | C13H10N2OSe |
Mr | 289.19 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 93 |
a, b, c (Å) | 8.5036 (15), 25.210 (5), 11.116 (2) |
α, β, γ (°) | 90, 96.814 (5), 90 |
V (Å3) | 2366.2 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 3.16 |
Crystal size (mm) | 0.30 × 0.20 × 0.04 |
Data collection | |
Diffractometer | Rigaku Mercury CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2010) |
Tmin, Tmax | 0.558, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15690, 4865, 3778 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.669 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.147, 1.07 |
No. of reflections | 4865 |
No. of parameters | 309 |
No. of restraints | 0 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.35, −1.03 |
Absolute structure | ? |
Absolute structure parameter | ? |
Computer programs: CrystalClear (Rigaku, 2010), SHELXTL (Sheldrick, 2008) and OLEX (Dolomanov et al., 2003), SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2003), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···N4i | 0.95 | 2.59 | 3.539 (12) | 176.9 |
Symmetry code: (i) x−1/2, −y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···N33i | 0.95 | 2.50 | 3.441 (7) | 172.3 |
C44—H44···N33ii | 0.95 | 2.59 | 3.457 (7) | 151.3 |
Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x, −y+3/2, z−1/2. |
Cg1 and Cg2 are the centroids of the Se1–C5 and C11–C16 rings, respectively, of polymorph (Ia). Cg3 is the centroid of the Se1–C5 ring of polymorph (Ib). Cg4, Cg5 and Cg6 are the centroids of the Se1–C5, S11–C15 and S21–C25 rings, respectively, of (IIb). Cg7 and Cg8 are the centroids of the Se1–C5 and C11–C16 rings, respectively, of (III). Cg9, Cg10 and Cg11 are the centroids of the Se1–C5, C21–C26 and C51–C56 rings, respectively, of (IV). |
Compound | Centroids | Cg···Cg |
(Ia) | Cg1···Cg2i | 3.6197 (19) |
(Ib) | Cg3···Cg3ii | 3.848 (3) |
(IIb) | Cg4···Cg5iii | 3.636 (4) |
Cg4···Cg6iv | 3.861 (4) | |
(III) | Cg7···Cg8v | 3.670 (4) |
(IV) | Cg9···Cg10vi | 3.930 (3) |
Cg11···Cg11vii | 3.898 (3) |
Symmetry codes: (i) -x + 2, -y, -z + 1; (ii) -x, -y + 1, -z + 1; (iii) x, y - 1, z; (iv) x, y + 1, z; (v) -x + 1, -y, -z + 1; (vi) -x + 2, -y + 1, -z + 1; (vii) -x + 1, -y + 1, -z + 1. |
Cg1 and Cg2 are the centroids of the C11–C16 and C21–C26 rings, respectively, of polymorph (Ia). Cg3 is the centroid of the C11–C16 ring of polymorph (Ib). Cg4 is the centroid of the C21–C26 ring of (III). Cg5 and Cg6 are the centroids of the C51–C56 and O11–C15 rings, respectively, of (IV). |
Compound | C—H···Cg | H···Cg | C···Cg | C—H···Cg |
(Ia) | C22—H22···Cg1i | 2.89 | 3.660 (3) | 139 |
C13—H13···Cg2i | 2.97 | 3.649 (3) | 130 | |
(Ib) | C16—H16···Cg3ii | 2.81 | 3.416 (6) | 122 |
C13—H13···Cg3iii | 2.94 | 3.621 (7) | 130 | |
(III) | C13—H13···Cg4iv | 2.77 | 3.497 (7) | 134 |
C25—H25···Cg4v | 2.93 | 3.673 (7) | 136 | |
(IV) | C23—H23···Cg5vi | 2.52 | 3.389 (5) | 151 |
C27—H27C···Cg6vii | 2.89 | 3.549 (6) | 125 |
Symmetry codes: (i) -x + 2, y + 1/2, -z + 1/2; (ii) x, -y + 1, z - 1/2; (iii) x, -y, z - 1/2; (iv) -x + 1, y + 1/2, -z + 3/2; (v) -x + 2, y - 1/2, -z + 3/2; (vi) x + 1, y, z; (vii) -x + 2, -y + 1, -z + 1. |
Interest in using organoselenium heterocycles as compounds with novel properties has expanded rapidly during the last three decades. This interest has focused on areas as diverse as pharmaceutically interesting compounds (Klayman & Gunther 1973; Mugesh et al., 2001; Nicolaou & Petasis, 1984) and new reagents with unusual reactivity profiles (Back, 2000; Wirth, 2000a,b). The selenation reagent 2,4-diphenyl-1,3-diselenadiphosphetane 2,4-diselenide, [PhP(Se)(µ-Se)]2, Woollins' reagent, is the selenium counterpart of the well known Lawesson's reagent. It has been shown to insert selenium into a wide range of different compounds, including in the formation of the title 2,5-diaryl-1,3,4-selenadiazoles (for examples, see Hua et al., 2009; Hua, Cordes et al. 2011; Hua, Griffin et al., 2011, and references therein). Five crystal structures have been determined for four selenadiazoles, two of which are polymorphs of each other, and another of which is a polymorph of a known structure; these are 2,5-diphenyl-1,3,4-selenadiazole, (Ia) (Fig. 1) and (Ib) (Fig. 2), 2,5-bis(thiophen-2-yl)-1,3,4-selenadiazole, (IIb) (Fig. 3), 2-(4-chlorophenyl)-5-phenyl-1,3,4-selenadiazole, (III) (Fig. 4), and 2-(furan-2-yl)-5-(p-tolyl)-1,3,4-selenadiazole, (IV) (Fig. 5). All five compounds were prepared according to published methods (Hua et al., 2009; Hua, Cordes et al., 2011), and crystals were grown in each case by the diffusion of hexane into a dichloromethane solution of the compound.
Three of the five structures have a single molecule of the compound in the asymmetric unit, the exceptions being polymorph (Ib) and compound (IV). In (Ib), the asymmetric unit comprises half a molecule of 2,5-diphenyl-1,3,4-selenadiazole, the other half being generated by twofold rotational symmetry, whereas in (IV), two independent molecules of 2-(furan-2-yl)-5-(p-tolyl)-1,3,4-selenadiazole form the asymmetric unit. The C—Se bond distances in (I)–(IV) vary from 1.861 (7) to 1.890 (4) Å, falling within the range of C—Se bond lengths (1.86–1.90 Å) seen in selenadiazoles (Hua et al., 2009; Hua, Cordes et al., 2011). These distances are shorter than would be expected for a C—Se single bond (ca 1.94 Å), indicating that some degree of delocalization occurs. Four of the five structures [excluding (Ib)] show the same near-planar molecular arrangement seen in previous selenadiazole structures (Hua et al., 2009; Hua, Cordes et al., 2011). The dihedral angles between peripheral ring planes and the selenadiazole rings range from 1.7 (4) to 13.5 (3)°, with the exception of polymorph (Ib), where the dihedral angle is 22.3 (2)°. Due to its rotational symmetry, this leads to the planes of its phenyl rings being inclined at 43.44 (17)° with respect to each other.
The predominant types of intermolecular interactions in these compounds are those involving their π-systems. All five of the structures show π–π stacking interactions, at a variety of centroid–centroid (Cg···Cg) distances. While some of these, with Cg···Cg distances in the range 3.6197 (19)–3.670 (4) Å, fall within the conventional range for π–π interactions, some show apparent π-stacking at distances as long as 3.930 (3) Å (Table 3). While π-interactions at such distances would conventionally be considered insignificant, in these cases the interactions are supported by acting in parallel with other interactions, including other π–π interactions and also C—H···π interactions (see below). All of the compounds, except for (IIb), also show C—H···π interactions, with C—H···Cg distances ranging from 2.52 to 2.97 Å (Table 4). While these longer distances would give rise to very weak interactions, due to their occurring at the conventional van der Waals limit, C—H···π interactions have been suggested to be effective at distances beyond this value (Nishio, 2004). In polymorph (Ib) and in (IV), these interactions occur in conjunction with π–π interactions, mutually reinforcing each other, as in these two compounds there is either sufficient angularity between the phenyl and selenadiazole rings [in (Ib)] or the presence of the tolyl methyl group [in (IV)] to allow for both C—H···π and π–π interactions between the same adjacent molecules. Further intramolecular interactions occur in (IIb) and (IV), where weak C—H···N hydrogen bonds contribute to the observed packing motif. These occur at H···N distances of 2.59 Å in (IIb), and 2.50 and 2.59 Å in (IV), with C···N separations of 3.539 (12), 3.422 (7) and 3.457 (8) Å, respectively.
While this similarity of molecular geometries and types of intramolecular interactions might suggest that similar packing modes would be observed, this is not found to be the case. The intermolecular interactions observed, namely π–π interactions, C—H···π interactions and weak C—H···N hydrogen bonds, combine in different ways, giving rise to a variety of packing motifs. In (Ia) (Fig. 6), chains formed by C—H···π interactions run along the b axis. These interact with adjacent chains by the formation of π-stacked dimers, giving rise to sheets in the (100) plane. In the cases of (Ib) (Fig. 6) and (IIb) (Fig. 7), both display two-dimensional sheets formed by the interaction of two different types of chains. Both show π-stacked chains, running along c in (Ib) and along b in (IIb), but the second type of chain is formed by C—H···π interactions along the c axis in (Ib), and by weak hydrogen bonds along the a axis in (IIb), and the resulting sheets occur in the (100) and (001) planes, respectively. The situation in (III) and (IV) is somewhat different, as each comprises a three-dimensional network formed by the linking together of two-dimensional sheets. In (III), two-dimensional sheets are formed in the (001) plane by C—H···π interactions (Fig. 8), whereas in (IV), sheets in the (100) plane are formed by a combination of C–H···π and π–π interactions, and C—H···N hydrogen bonding (Fig. 9). In both compounds, these sheets are then linked together into a three-dimensional network by the formation of π-stacked dimers between sheets.
For 2,5-diphenyl-1,3,4-selenadiazole, (I), two visually similar types of polymorphic crystals form under the same conditions. Both of these display a monoclinic unit cell, with polymorph (Ia) crystallizing in the space group P21/c and polymorph (Ib) in space group C2/c. On a molecular level, there is one key structural difference between the two forms, which appears to give rise to many of the differences observed in packing. This is the difference in the dihedral angles between the phenyl rings and the selenadiazole ring, with polymorph (Ia) showing angles of 3.35 (16) and 4.11 (16)°, whereas polymorph (Ib) shows a single dihedral angle of 22.3 (2)°. These differences can be seen to lead directly to differences in packing (Fig. 6), as the twist of the phenyl rings changes both the distance and angle possible for π–π interactions, inducing a molecular offset from the chain axis in (Ib), and also makes it possible for both π–π and C—H···π interactions to occur in the same molecular chain.
In the case of (IIb), the crystals appeared to be slightly visually different to those previously found for (IIa) (Hua, Cordes et al., 2011), and structure analysis revealed it to be a polymorphic form. Polymorph (IIb) crystallizes in the orthorhombic space group Pca21, although with broadly similar unit-cell parameters to the known structure, which crystallizes in the monoclinic space group P21/c. There is little on a gross structural level to indicate why a different polymorphic form occurs, a fit of all non-H atoms of polymorph (IIb) to those of polymorph (IIa) having an r.m.s. deviation of 0.052 Å. Additionally, there are similarities in the packing of the two polymorphs, but the differences between them do become more apparent as the interactions which give rise to the packing are considered. Both polymorphs display π-stacked chains running along the b axis, but these are assembled differently. In (IIb), the π-overlaps occur between the selenadiazole ring and both thiophene rings, whereas in (IIa), two different sets of π-interactions give rise to a more zigzag chain. Furthermore, (IIb) also shows chains running along the a axis formed by weak C—H···N? hydrogen bonding, the combination of these two sets of interactions giving rise to sheets in the (001) plane, while (IIa) shows no other intermolecular interactions.