Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501305X/fl6158sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680501305X/fl6158Isup2.hkl |
CCDC reference: 274393
Key indicators
- Single-crystal X-ray study
- T = 303 K
- Mean (C-C) = 0.007 Å
- R factor = 0.032
- wR factor = 0.085
- Data-to-parameter ratio = 9.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT035_ALERT_1_A No _chemical_absolute_configuration info given . ?
Author Response: Compound (I) exhibits a stereogenic axis. The absolute configuration along this axis (C2-S2) is M (which corresponds to axial S). We have refrained from discussing the absolute configuration in this CIF for the following reason: The Flack parameter for M-(I) is -0.09 (13). On the assumption of P configuration along the C-S axis, a Flack paramter of 0.24(14) is obtained. |
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.75 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C9 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C10 H5 Cl4 N S2
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.99 From the CIF: _reflns_number_total 1444 Count of symmetry unique reflns 1455 Completeness (_total/calc) 99.24% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Diffractometer Control Software (Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: CAD-4 Diffractometer Control Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2003 (Spek, 1990, 2003) and ORTEP-3 (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.
C10H5Cl4NS2 | Dx = 1.704 Mg m−3 |
Mr = 345.07 | Melting point: 375 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.353 (3) Å | Cell parameters from 25 reflections |
b = 6.107 (1) Å | θ = 4.5–14.0° |
c = 10.882 (2) Å | µ = 1.16 mm−1 |
β = 102.23 (2)° | T = 303 K |
V = 672.4 (3) Å3 | Needle, colourless |
Z = 2 | 0.75 × 0.13 × 0.05 mm |
F(000) = 344 |
Enraf–Nonius CAD-4 diffractometer | 1165 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 26.0°, θmin = 4.1° |
ω/2θ scans | h = −12→12 |
Absorption correction: ψ scan (North et al., 1968) | k = −7→0 |
Tmin = 0.865, Tmax = 0.943 | l = −13→13 |
2883 measured reflections | 3 standard reflections every 120 min |
1444 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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0505P)2] where P = (Fo2 + 2Fc2)/3 |
1444 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.32 e Å−3 |
1 restraint | Δρmin = −0.29 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. |
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 | ||
C2 | −0.2643 (4) | −0.5673 (7) | −0.1502 (4) | 0.0516 (10) | |
C4 | −0.4311 (4) | −0.7111 (8) | −0.2802 (3) | 0.0488 (9) | |
C5 | −0.3548 (5) | −0.8932 (8) | −0.2516 (4) | 0.0614 (12) | |
H4 | −0.3777 | −1.0319 | −0.2843 | 0.074* | |
C6 | −0.5623 (4) | −0.7015 (8) | −0.3654 (3) | 0.0496 (9) | |
C7 | −0.6369 (4) | −0.5129 (9) | −0.3766 (4) | 0.0610 (11) | |
H7 | −0.6040 | −0.3903 | −0.3296 | 0.073* | |
C8 | −0.7592 (5) | −0.5029 (10) | −0.4561 (5) | 0.0724 (14) | |
H8 | −0.8089 | −0.3751 | −0.4613 | 0.087* | |
C9 | −0.8081 (5) | −0.6810 (12) | −0.5279 (4) | 0.0699 (14) | |
C10 | −0.7364 (5) | −0.8727 (12) | −0.5189 (5) | 0.0752 (14) | |
H10 | −0.7704 | −0.9937 | −0.5669 | 0.090* | |
C11 | −0.6134 (5) | −0.8845 (10) | −0.4380 (4) | 0.0621 (11) | |
H11 | −0.5648 | −1.0136 | −0.4318 | 0.075* | |
C12 | −0.2405 (4) | −0.3427 (8) | 0.0739 (4) | 0.0529 (10) | |
N3 | −0.3773 (3) | −0.5244 (6) | −0.2221 (3) | 0.0488 (8) | |
S1 | −0.21321 (12) | −0.8334 (2) | −0.14898 (13) | 0.0666 (4) | |
S2 | −0.16012 (10) | −0.37398 (19) | −0.05817 (10) | 0.0552 (3) | |
Cl1 | −0.95979 (14) | −0.6656 (4) | −0.63124 (14) | 0.1097 (7) | |
Cl2 | −0.13319 (11) | −0.1703 (3) | 0.17865 (12) | 0.0755 (4) | |
Cl3 | −0.39691 (10) | −0.2168 (3) | 0.03080 (11) | 0.0693 (4) | |
Cl4 | −0.26126 (14) | −0.5942 (2) | 0.14672 (13) | 0.0796 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.057 (2) | 0.036 (2) | 0.066 (2) | 0.0016 (19) | 0.0224 (19) | −0.006 (2) |
C4 | 0.061 (2) | 0.040 (2) | 0.0501 (19) | 0.0027 (19) | 0.0230 (17) | −0.003 (2) |
C5 | 0.070 (3) | 0.040 (2) | 0.074 (3) | 0.007 (2) | 0.016 (2) | −0.011 (2) |
C6 | 0.059 (2) | 0.048 (2) | 0.0464 (19) | −0.001 (2) | 0.0202 (16) | 0.001 (2) |
C7 | 0.065 (3) | 0.050 (3) | 0.070 (3) | 0.004 (2) | 0.018 (2) | 0.001 (2) |
C8 | 0.064 (3) | 0.068 (4) | 0.087 (3) | 0.018 (3) | 0.021 (3) | 0.019 (3) |
C9 | 0.067 (3) | 0.086 (4) | 0.057 (2) | −0.012 (3) | 0.0137 (19) | 0.017 (3) |
C10 | 0.086 (3) | 0.075 (4) | 0.064 (3) | −0.019 (3) | 0.015 (2) | −0.001 (3) |
C11 | 0.072 (3) | 0.055 (3) | 0.061 (2) | −0.005 (3) | 0.018 (2) | −0.008 (3) |
C12 | 0.054 (2) | 0.047 (2) | 0.057 (2) | 0.003 (2) | 0.0109 (17) | 0.000 (2) |
N3 | 0.0555 (19) | 0.0412 (19) | 0.0521 (18) | 0.0033 (16) | 0.0169 (15) | −0.0017 (17) |
S1 | 0.0645 (7) | 0.0420 (6) | 0.0891 (8) | 0.0127 (6) | 0.0068 (6) | −0.0079 (6) |
S2 | 0.0506 (5) | 0.0463 (6) | 0.0721 (7) | −0.0006 (5) | 0.0205 (5) | −0.0060 (5) |
Cl1 | 0.0754 (8) | 0.145 (2) | 0.0964 (10) | −0.0191 (11) | −0.0094 (7) | 0.0389 (13) |
Cl2 | 0.0691 (7) | 0.0732 (9) | 0.0795 (7) | −0.0028 (7) | 0.0048 (5) | −0.0244 (7) |
Cl3 | 0.0522 (5) | 0.0811 (9) | 0.0765 (7) | 0.0151 (6) | 0.0183 (5) | −0.0035 (7) |
Cl4 | 0.1026 (10) | 0.0642 (9) | 0.0727 (7) | −0.0048 (7) | 0.0198 (7) | 0.0150 (6) |
C2—N3 | 1.289 (6) | C8—C9 | 1.372 (9) |
C2—S1 | 1.708 (4) | C8—H8 | 0.9300 |
C2—S2 | 1.761 (4) | C9—C10 | 1.378 (9) |
C4—C5 | 1.362 (7) | C9—Cl1 | 1.730 (5) |
C4—N3 | 1.365 (6) | C10—C11 | 1.389 (7) |
C4—C6 | 1.474 (5) | C10—H10 | 0.9300 |
C5—S1 | 1.684 (5) | C11—H11 | 0.9300 |
C5—H4 | 0.9300 | C12—Cl4 | 1.762 (5) |
C6—C7 | 1.378 (7) | C12—Cl2 | 1.762 (4) |
C6—C11 | 1.406 (7) | C12—Cl3 | 1.764 (4) |
C7—C8 | 1.375 (6) | C12—S2 | 1.817 (4) |
C7—H7 | 0.9300 | ||
N3—C2—S1 | 116.0 (3) | C8—C9—C10 | 120.3 (5) |
N3—C2—S2 | 125.2 (3) | C8—C9—Cl1 | 120.1 (5) |
S1—C2—S2 | 118.8 (3) | C10—C9—Cl1 | 119.6 (5) |
C5—C4—N3 | 114.6 (4) | C9—C10—C11 | 119.8 (6) |
C5—C4—C6 | 126.1 (4) | C9—C10—H10 | 120.1 |
N3—C4—C6 | 119.3 (4) | C11—C10—H10 | 120.1 |
C4—C5—S1 | 110.9 (4) | C10—C11—C6 | 120.0 (5) |
C4—C5—H4 | 124.6 | C10—C11—H11 | 120.0 |
S1—C5—H4 | 124.6 | C6—C11—H11 | 120.0 |
C7—C6—C11 | 118.5 (4) | Cl4—C12—Cl2 | 110.5 (2) |
C7—C6—C4 | 120.9 (4) | Cl4—C12—Cl3 | 107.9 (2) |
C11—C6—C4 | 120.6 (4) | Cl2—C12—Cl3 | 109.2 (3) |
C8—C7—C6 | 121.1 (5) | Cl4—C12—S2 | 112.6 (3) |
C8—C7—H7 | 119.4 | Cl2—C12—S2 | 104.1 (2) |
C6—C7—H7 | 119.4 | Cl3—C12—S2 | 112.6 (2) |
C9—C8—C7 | 120.1 (5) | C2—N3—C4 | 109.9 (4) |
C9—C8—H8 | 119.9 | C5—S1—C2 | 88.7 (2) |
C7—C8—H8 | 119.9 | C2—S2—C12 | 101.1 (2) |
N3—C4—C5—S1 | 0.6 (5) | C7—C6—C11—C10 | 0.1 (7) |
C6—C4—C5—S1 | −179.2 (3) | C4—C6—C11—C10 | −179.3 (4) |
C5—C4—C6—C7 | 172.8 (4) | S1—C2—N3—C4 | 1.0 (4) |
N3—C4—C6—C7 | −7.0 (6) | S2—C2—N3—C4 | 179.5 (3) |
C5—C4—C6—C11 | −7.8 (6) | C5—C4—N3—C2 | −1.0 (5) |
N3—C4—C6—C11 | 172.4 (4) | C6—C4—N3—C2 | 178.8 (3) |
C11—C6—C7—C8 | 0.4 (7) | C4—C5—S1—C2 | 0.0 (4) |
C4—C6—C7—C8 | 179.9 (4) | N3—C2—S1—C5 | −0.6 (4) |
C6—C7—C8—C9 | −1.2 (8) | S2—C2—S1—C5 | −179.2 (3) |
C7—C8—C9—C10 | 1.4 (8) | N3—C2—S2—C12 | 78.4 (4) |
C7—C8—C9—Cl1 | −178.1 (4) | S1—C2—S2—C12 | −103.1 (3) |
C8—C9—C10—C11 | −0.8 (8) | Cl4—C12—S2—C2 | 54.9 (3) |
Cl1—C9—C10—C11 | 178.7 (4) | Cl2—C12—S2—C2 | 174.6 (2) |
C9—C10—C11—C6 | 0.1 (7) | Cl3—C12—S2—C2 | −67.3 (3) |