Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001838/cf6485sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001838/cf6485Isup2.hkl |
CCDC reference: 298674
Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C10H4Cl5NO2S | Z = 2 |
Mr = 379.46 | F(000) = 376.00 |
Triclinic, P1 | Dx = 1.727 Mg m−3 |
Hall symbol: -P 1 | Melting point = 386–388 K |
a = 6.6504 (4) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 10.7872 (3) Å | Cell parameters from 6436 reflections |
c = 10.857 (4) Å | θ = 3.1–30.1° |
α = 70.481 (4)° | µ = 1.13 mm−1 |
β = 87.411 (8)° | T = 294 K |
γ = 83.680 (7)° | Block, yellow |
V = 729.6 (3) Å3 | 0.40 × 0.30 × 0.25 mm |
Rigaku R-AXIS RAPID diffractometer | 3450 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.021 |
ω scans | θmax = 30.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.677, Tmax = 0.760 | k = −14→15 |
8204 measured reflections | l = −15→15 |
4303 independent reflections |
Refinement on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.079 | Chebychev polynomial with three parameters (Carruthers & Watkin, 1979): 9.9084, 2.2048 and 6.4348 |
wR(F2) = 0.085 | (Δ/σ)max = 0.009 |
S = 1.10 | Δρmax = 1.24 e Å−3 |
3450 reflections | Δρmin = −0.77 e Å−3 |
176 parameters |
Geometry. Least Squares Planes ————– Plane number 1 ———– Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] 0.1784 0.0020 C2 [1;0;0;0] -0.3781 0.0042 C3 [1;0;0;0] 0.1812 0.0020 C4 [1;0;0;0] -0.0613 0.0007 Additional Atoms Distance e.s.d. Mean deviation from plane is 0.1997 angstrom Chi-squared: 9329.680 ————– Plane number 2 ————— Atoms Defining Plane Distance e.s.d. C5 [1;0;0;0] -0.0102 0.0026 C6 [1;0;0;0] 0.0087 0.0030 C7 [1;0;0;0] 0.0003 0.0032 C8 [1;0;0;0] -0.0069 0.0032 C9 [1;0;0;0] 0.0036 0.0035 C10 [1;0;0;0] 0.0071 0.0032 Additional Atoms Distance e.s.d. Mean deviation from plane is 0.0061 angstrom Chi-squared: 15.255 Dihedral angles between least-squares planes ——————————– plane plane angle e.s.d. 1 2 59.489 0.194 |
Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.1743 (2) | −0.03972 (12) | 0.8236 (1) | 0.0945 (4) | |
Cl2 | −0.2755 (2) | 0.20470 (13) | 0.60950 (12) | 0.0820 (3) | |
Cl3 | 0.2609 (2) | 0.04192 (12) | 0.8303 (1) | 0.0938 (4) | |
Cl4 | 0.2323 (3) | 0.14109 (11) | 0.45793 (12) | 0.0961 (4) | |
Cl5 | 0.5769 (2) | 0.27694 (13) | −0.10412 (12) | 0.0897 (4) | |
S1 | 0.3263 (2) | 0.41666 (8) | 0.39865 (8) | 0.0575 (2) | |
O2 | 0.2029 (5) | 0.4758 (3) | 0.6074 (3) | 0.0717 (9) | |
O1 | 0.0587 (5) | 0.3572 (3) | 0.7825 (3) | 0.0711 (8) | |
N1 | 0.1338 (5) | 0.3733 (3) | 0.6743 (3) | 0.0554 (8) | |
C1 | −0.0981 (8) | 0.1058 (5) | 0.7168 (4) | 0.0772 (13) | |
C2 | 0.0791 (8) | 0.1423 (4) | 0.7181 (4) | 0.0748 (13) | |
C3 | 0.1440 (6) | 0.2659 (3) | 0.6240 (3) | 0.0581 (9) | |
C4 | 0.2248 (6) | 0.2784 (3) | 0.5043 (4) | 0.0569 (9) | |
C5 | 0.3938 (6) | 0.3702 (3) | 0.2590 (3) | 0.0558 (9) | |
C6 | 0.2498 (6) | 0.3865 (4) | 0.1646 (4) | 0.0622 (10) | |
C7 | 0.3068 (7) | 0.3572 (4) | 0.0523 (4) | 0.0642 (11) | |
C8 | 0.5061 (7) | 0.3144 (3) | 0.0362 (4) | 0.0621 (10) | |
C9 | 0.6512 (7) | 0.3006 (4) | 0.1272 (4) | 0.0710 (12) | |
C10 | 0.5929 (6) | 0.3296 (4) | 0.2395 (4) | 0.0668 (11) | |
H1 | 0.6898 | 0.3212 | 0.3042 | 0.081* | |
H2 | 0.7879 | 0.2726 | 0.1123 | 0.086* | |
H3 | 0.2114 | 0.3676 | −0.0139 | 0.078* | |
H4 | 0.1137 | 0.4167 | 0.1781 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1222 (11) | 0.0700 (6) | 0.0911 (8) | −0.0409 (7) | 0.0331 (7) | −0.0211 (6) |
Cl2 | 0.0688 (7) | 0.0935 (8) | 0.0757 (6) | −0.0177 (5) | −0.0111 (5) | −0.0129 (6) |
Cl3 | 0.0921 (8) | 0.0734 (7) | 0.0921 (8) | −0.0097 (6) | −0.0301 (6) | 0.0082 (6) |
Cl4 | 0.1626 (13) | 0.0636 (6) | 0.0783 (7) | −0.0440 (7) | 0.0476 (8) | −0.0410 (5) |
Cl5 | 0.1246 (10) | 0.0849 (7) | 0.0705 (6) | −0.0210 (7) | 0.0293 (6) | −0.0411 (6) |
S1 | 0.0748 (6) | 0.0516 (4) | 0.0494 (4) | −0.0169 (4) | 0.0077 (4) | −0.0188 (3) |
O2 | 0.096 (2) | 0.059 (1) | 0.070 (2) | −0.025 (1) | 0.012 (1) | −0.0313 (13) |
O1 | 0.092 (2) | 0.073 (2) | 0.054 (1) | −0.006 (1) | 0.0104 (13) | −0.0299 (12) |
N1 | 0.063 (2) | 0.055 (2) | 0.053 (2) | −0.0051 (12) | 0.0006 (12) | −0.0233 (12) |
C1 | 0.099 (3) | 0.076 (3) | 0.062 (2) | −0.022 (2) | 0.014 (2) | −0.028 (2) |
C2 | 0.100 (3) | 0.066 (2) | 0.063 (2) | −0.017 (2) | 0.012 (2) | −0.026 (2) |
C3 | 0.076 (2) | 0.049 (2) | 0.053 (2) | −0.013 (2) | 0.009 (2) | −0.0209 (13) |
C4 | 0.071 (2) | 0.048 (2) | 0.057 (2) | −0.013 (1) | 0.008 (2) | −0.0223 (13) |
C5 | 0.070 (2) | 0.052 (2) | 0.048 (2) | −0.014 (2) | 0.007 (1) | −0.0173 (13) |
C6 | 0.066 (2) | 0.063 (2) | 0.058 (2) | −0.001 (2) | −0.003 (2) | −0.021 (2) |
C7 | 0.084 (3) | 0.061 (2) | 0.049 (2) | −0.010 (2) | −0.002 (2) | −0.019 (2) |
C8 | 0.086 (3) | 0.047 (2) | 0.054 (2) | −0.015 (2) | 0.018 (2) | −0.0170 (13) |
C9 | 0.073 (3) | 0.074 (2) | 0.069 (2) | −0.010 (2) | 0.015 (2) | −0.028 (2) |
C10 | 0.066 (2) | 0.071 (2) | 0.067 (2) | −0.010 (2) | 0.002 (2) | −0.026 (2) |
Cl1—C1 | 1.724 (5) | C3—C4 | 1.354 (5) |
Cl2—C1 | 1.704 (5) | C5—C6 | 1.389 (6) |
Cl3—C2 | 1.755 (5) | C5—C10 | 1.378 (6) |
Cl4—C4 | 1.711 (4) | C6—C7 | 1.385 (6) |
Cl5—C8 | 1.735 (4) | C6—H4 | 0.950 |
S1—C4 | 1.733 (3) | C7—C8 | 1.378 (6) |
S1—C5 | 1.774 (4) | C7—H3 | 0.950 |
O2—N1 | 1.227 (4) | C8—C9 | 1.374 (6) |
O1—N1 | 1.221 (4) | C9—C10 | 1.385 (7) |
N1—C3 | 1.431 (5) | C9—H2 | 0.950 |
C1—C2 | 1.285 (8) | C10—H1 | 0.950 |
C2—C3 | 1.478 (5) | ||
Cl1···Cl2 | 2.909 (2) | C4···H4 | 3.431 (5) |
Cl1···Cl3 | 3.127 (2) | C5···Cl4 | 2.956 (3) |
Cl1···C2 | 2.657 (5) | C5···C4 | 2.747 (5) |
Cl2···Cl1 | 2.909 (2) | C5···C7 | 2.395 (6) |
Cl2···C2 | 2.603 (5) | C5···C8 | 2.735 (6) |
Cl2···C3 | 2.959 (4) | C5···C9 | 2.399 (6) |
Cl2···C4i | 3.484 (4) | C5···H1 | 2.020 (6) |
Cl2···C4 | 3.555 (4) | C5···H2 | 3.263 (6) |
Cl2···H1i | 3.137 (4) | C5···H3 | 3.261 (6) |
Cl3···Cl1 | 3.127 (2) | C5···H4 | 2.035 (6) |
Cl3···O1 | 3.394 (3) | C6···Cl4 | 3.400 (4) |
Cl3···N1 | 3.432 (3) | C6···S1 | 2.744 (5) |
Cl3···C1 | 2.651 (5) | C6···C4 | 3.478 (5) |
Cl3···C3 | 2.754 (3) | C6···C8 | 2.381 (6) |
Cl4···S1 | 2.956 (2) | C6···C9 | 2.785 (6) |
Cl4···C1 | 3.433 (5) | C6···C10 | 2.402 (6) |
Cl4···C2 | 2.963 (5) | C6···H1 | 3.254 (6) |
Cl4···C3 | 2.601 (4) | C6···H2i | 3.566 (7) |
Cl4···C5 | 2.956 (3) | C6···H3 | 2.045 (6) |
Cl4···C6 | 3.400 (4) | C7···O1iii | 3.426 (5) |
Cl4···C10 | 3.585 (4) | C7···C5 | 2.395 (6) |
Cl4···H4 | 3.515 (3) | C7···C9 | 2.410 (6) |
S1···Cl4 | 2.956 (2) | C7···C9iv | 3.588 (6) |
S1···O2 | 2.626 (3) | C7···C10 | 2.768 (6) |
S1···N1 | 3.109 (3) | C7···H2 | 3.262 (6) |
S1···C3 | 2.759 (3) | C7···H4 | 2.043 (6) |
S1···C6 | 2.744 (5) | C8···C5 | 2.735 (6) |
S1···C10 | 2.730 (5) | C8···C6 | 2.381 (6) |
S1···H1 | 2.809 (4) | C8···C10 | 2.368 (6) |
S1···H4 | 2.835 (4) | C8···H1 | 3.232 (6) |
O2···S1 | 2.626 (3) | C8···H2 | 2.026 (6) |
O2···O1 | 2.157 (4) | C8···H3 | 2.026 (6) |
O2···C2 | 3.569 (5) | C8···H4 | 3.247 (6) |
O2···C3 | 2.286 (5) | C9···C5 | 2.399 (6) |
O2···C4 | 2.706 (5) | C9···C6 | 2.785 (6) |
O1···Cl3 | 3.394 (3) | C9···C7 | 2.410 (6) |
O1···O2 | 2.157 (4) | C9···C7iv | 3.588 (6) |
O1···C1 | 3.306 (7) | C9···H1 | 2.037 (7) |
O1···C2 | 2.624 (6) | C9···H3 | 3.259 (6) |
O1···C3 | 2.274 (5) | C9···H3iv | 3.582 (6) |
O1···C4 | 3.504 (5) | C9···H4ii | 3.577 (7) |
N1···Cl3 | 3.432 (3) | C10···Cl4 | 3.585 (4) |
N1···S1 | 3.109 (3) | C10···S1 | 2.730 (5) |
N1···C1 | 3.308 (6) | C10···C6 | 2.402 (6) |
N1···C2 | 2.441 (6) | C10···C7 | 2.768 (6) |
N1···C4 | 2.419 (5) | C10···C8 | 2.368 (6) |
C1···Cl3 | 2.651 (5) | C10···H2 | 2.048 (7) |
C1···Cl4 | 3.433 (5) | C10···H4 | 3.255 (6) |
C1···O1 | 3.306 (7) | H1···Cl2ii | 3.137 (4) |
C1···N1 | 3.308 (6) | H1···S1 | 2.809 (4) |
C1···C3 | 2.427 (6) | H1···C5 | 2.020 (6) |
C1···C4 | 3.311 (6) | H1···C6 | 3.254 (6) |
C2···Cl1 | 2.657 (5) | H1···C8 | 3.232 (6) |
C2···Cl2 | 2.603 (5) | H1···C9 | 2.037 (7) |
C2···Cl4 | 2.963 (5) | H2···C5 | 3.263 (6) |
C2···O2 | 3.569 (5) | H2···C6ii | 3.566 (7) |
C2···O1 | 2.624 (6) | H2···C7 | 3.262 (6) |
C2···N1 | 2.441 (6) | H2···C8 | 2.026 (6) |
C2···C4 | 2.513 (5) | H2···C10 | 2.048 (7) |
C3···Cl2 | 2.959 (4) | H3···O1iii | 2.515 (5) |
C3···Cl3 | 2.754 (3) | H3···N1iii | 3.427 (5) |
C3···Cl4 | 2.601 (4) | H3···C5 | 3.261 (6) |
C3···S1 | 2.759 (3) | H3···C6 | 2.045 (6) |
C3···O2 | 2.286 (5) | H3···C8 | 2.026 (6) |
C3···O1 | 2.274 (5) | H3···C9 | 3.259 (6) |
C3···C1 | 2.427 (6) | H3···C9iv | 3.582 (6) |
C4···Cl2 | 3.555 (4) | H4···Cl4 | 3.515 (3) |
C4···Cl2ii | 3.484 (4) | H4···S1 | 2.835 (4) |
C4···O2 | 2.706 (5) | H4···C4 | 3.431 (5) |
C4···O1 | 3.504 (5) | H4···C5 | 2.035 (6) |
C4···N1 | 2.419 (5) | H4···C7 | 2.043 (6) |
C4···C6 | 3.311 (6) | H4···C8 | 3.247 (6) |
C4···C2 | 2.513 (5) | H4···C9i | 3.577 (7) |
C4···C5 | 2.747 (5) | H4···C10 | 3.255 (6) |
C4···C6 | 3.478 (5) | ||
C4—S1—C5 | 103.1 (2) | C10—C5—S1 | 119.5 (3) |
C3—N1—O2 | 118.5 (3) | C7—C6—H4 | 120.9 |
C3—N1—O1 | 117.9 (3) | C7—C6—C5 | 119.4 (4) |
O2—N1—O1 | 123.6 (4) | H4—C6—C5 | 119.7 |
C2—C1—Cl1 | 123.3 (4) | C8—C7—H3 | 119.9 |
C2—C1—Cl2 | 120.5 (3) | C8—C7—C6 | 119.0 (4) |
Cl1—C1—Cl2 | 116.1 (3) | H3—C7—C6 | 121.1 |
C3—C2—Cl3 | 116.6 (4) | C9—C8—Cl5 | 118.7 (3) |
C3—C2—C1 | 122.8 (4) | C9—C8—C7 | 122.3 (4) |
Cl3—C2—C1 | 120.6 (3) | Cl5—C8—C7 | 119.0 (3) |
C4—C3—N1 | 120.5 (3) | C10—C9—H2 | 121.5 |
C4—C3—C2 | 125.1 (4) | C10—C9—C8 | 118.3 (4) |
N1—C3—C2 | 114.1 (3) | H2—C9—C8 | 120.3 |
S1—C4—C3 | 126.2 (3) | H1—C10—C5 | 119.2 |
C6—C5—C10 | 120.5 (4) | H1—C10—C9 | 120.3 |
C6—C5—S1 | 119.8 (3) | C5—C10—C9 | 120.5 (4) |
C5—S1—C4—Cl4 | 4.6 (3) | C10—C5—C6—C7 | 2.1 (5) |
C5—S1—C4—C3 | −177.6 (3) | C10—C5—C6—H4 | −178.3 |
C4—S1—C5—C6 | 84.8 (3) | S1—C5—C10—C9 | −176.1 (3) |
C4—S1—C5—C10 | −101.0 (3) | S1—C5—C10—H1 | 4.3 |
O2—N1—C3—C2 | 173.1 (4) | C6—C5—C10—C9 | −1.9 (6) |
O2—N1—C3—C4 | −1.2 (5) | C6—C5—C10—H1 | 178.5 |
O1—N1—C3—C2 | −6.0 (5) | C5—C6—C7—C8 | −0.9 (6) |
O1—N1—C3—C4 | 179.7 (3) | C5—C6—C7—H3 | −179.9 |
Cl1—C1—C2—Cl3 | 1.1 (8) | H4—C6—C7—C8 | 179.5 |
Cl1—C1—C2—C3 | 178.6 (4) | H4—C6—C7—H3 | 0.7 |
Cl2—C1—C2—Cl3 | 179.0 (4) | C6—C7—C8—Cl5 | 179.6 (3) |
Cl2—C1—C2—C3 | −3.5 (8) | C6—C7—C8—C9 | −0.5 (6) |
Cl3—C2—C3—N1 | −83.0 (5) | H3—C7—C8—Cl5 | −1.5 |
Cl3—C2—C3—C4 | 91.0 (5) | H3—C7—C8—C9 | 178.4 |
C1—C2—C3—N1 | 99.4 (6) | Cl5—C8—C9—C10 | −179.4 (3) |
C1—C2—C3—C4 | −86.6 (6) | Cl5—C8—C9—H2 | 1.2 |
N1—C3—C4—Cl4 | 178.7 (3) | C7—C8—C9—C10 | 0.7 (6) |
N1—C3—C4—S1 | 0.8 (6) | C7—C8—C9—H2 | −178.7 |
C2—C3—C4—S1 | −172.9 (3) | C8—C9—C10—C5 | 0.5 (6) |
C2—C3—C4—Cl4 | 5.0 (5) | C8—C9—C10—H1 | −179.9 |
S1—C5—C6—C7 | 176.3 (3) | H2—C9—C10—C5 | 179.9 |
S1—C5—C6—H4 | −4.2 | H2—C9—C10—H1 | −0.5 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y, z−1; (iv) −x+1, −y+1, −z. |