Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040736/hk2138sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040736/hk2138Isup2.hkl |
CCDC reference: 627796
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.010 Å
- R factor = 0.059
- wR factor = 0.160
- Data-to-parameter ratio = 8.1
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.102 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.10 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.07 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C10 - C11 ... 1.43 Ang. PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.20
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 25.97 From the CIF: _reflns_number_total 1469 Count of symmetry unique reflns 1472 Completeness (_total/calc) 99.80% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C14H10ClN3S2 | F(000) = 328 |
Mr = 319.82 | Dx = 1.505 Mg m−3 |
Monoclinic, P21 | Melting point: 141.5 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 5.5690 (11) Å | Cell parameters from 25 reflections |
b = 9.5120 (19) Å | θ = 9–13° |
c = 13.372 (3) Å | µ = 0.56 mm−1 |
β = 95.05 (3)° | T = 294 K |
V = 705.6 (3) Å3 | Block, yellow |
Z = 2 | 0.40 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 1306 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.102 |
Graphite monochromator | θmax = 26.0°, θmin = 1.5° |
ω/2θ scans | h = 0→6 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.808, Tmax = 0.897 | l = −16→16 |
1620 measured reflections | 3 standard reflections every 120 min |
1469 independent reflections | intensity decay: none |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.160 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.99 e Å−3 |
1469 reflections | Δρmin = −0.48 e Å−3 |
181 parameters | Extinction correction: SHELXL97 |
1 restraint | Extinction coefficient: 0.094 (12) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.0 (2) |
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 | ||
Cl | 1.0713 (4) | 0.6876 (3) | 0.54197 (17) | 0.0667 (6) | |
S1 | 0.6821 (3) | 0.86502 (18) | 0.87800 (11) | 0.0431 (4) | |
S2 | 0.9283 (3) | 1.01255 (19) | 0.72387 (11) | 0.0451 (5) | |
N1 | 1.3816 (11) | 1.2196 (8) | 0.8766 (5) | 0.0603 (18) | |
N2 | 0.9976 (9) | 1.0482 (6) | 1.0250 (3) | 0.0386 (12) | |
N3 | 0.8268 (12) | 1.0893 (9) | 1.1646 (5) | 0.0597 (18) | |
C1 | 0.5819 (15) | 0.8890 (9) | 0.3648 (5) | 0.058 (2) | |
H1A | 0.5418 | 0.8964 | 0.2960 | 0.070* | |
C2 | 0.4508 (14) | 0.9610 (9) | 0.4320 (6) | 0.0568 (19) | |
H2A | 0.3222 | 1.0175 | 0.4079 | 0.068* | |
C3 | 0.5077 (13) | 0.9501 (9) | 0.5318 (5) | 0.0501 (18) | |
H3B | 0.4188 | 1.0007 | 0.5752 | 0.060* | |
C4 | 0.6978 (11) | 0.8643 (8) | 0.5719 (4) | 0.0413 (14) | |
C5 | 0.8255 (12) | 0.7961 (8) | 0.5037 (5) | 0.0450 (15) | |
C6 | 0.7702 (13) | 0.8073 (9) | 0.4014 (5) | 0.0522 (17) | |
H6A | 0.8615 | 0.7592 | 0.3575 | 0.063* | |
C7 | 0.7686 (11) | 0.8515 (8) | 0.6834 (5) | 0.0445 (15) | |
H7A | 0.8797 | 0.7720 | 0.6945 | 0.053* | |
C8 | 0.5675 (12) | 0.8331 (9) | 0.7489 (5) | 0.0492 (18) | |
H8A | 0.5036 | 0.7384 | 0.7420 | 0.059* | |
H8B | 0.4386 | 0.8987 | 0.7292 | 0.059* | |
C9 | 0.8994 (10) | 0.9877 (7) | 0.8510 (4) | 0.0344 (13) | |
C10 | 1.0378 (11) | 1.0579 (7) | 0.9224 (4) | 0.0390 (14) | |
C11 | 1.2279 (12) | 1.1483 (9) | 0.8958 (5) | 0.0460 (16) | |
C12 | 1.1362 (12) | 0.9815 (8) | 1.1002 (5) | 0.0459 (16) | |
H12A | 1.2772 | 0.9308 | 1.0944 | 0.055* | |
C13 | 1.0247 (14) | 1.0048 (10) | 1.1856 (5) | 0.0573 (19) | |
H13A | 1.0752 | 0.9687 | 1.2486 | 0.069* | |
C14 | 0.8159 (13) | 1.1098 (9) | 1.0706 (5) | 0.0499 (17) | |
H14A | 0.6946 | 1.1623 | 1.0361 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0527 (10) | 0.0630 (12) | 0.0844 (14) | 0.0137 (10) | 0.0061 (9) | 0.0074 (11) |
S1 | 0.0442 (8) | 0.0492 (9) | 0.0363 (7) | −0.0095 (8) | 0.0052 (6) | 0.0034 (7) |
S2 | 0.0484 (9) | 0.0544 (10) | 0.0326 (7) | −0.0183 (8) | 0.0040 (6) | −0.0004 (7) |
N1 | 0.047 (3) | 0.072 (5) | 0.061 (4) | −0.020 (3) | −0.001 (3) | 0.009 (3) |
N2 | 0.034 (2) | 0.048 (3) | 0.034 (3) | 0.004 (2) | 0.002 (2) | −0.001 (2) |
N3 | 0.052 (3) | 0.083 (5) | 0.046 (3) | 0.001 (4) | 0.012 (3) | −0.011 (4) |
C1 | 0.077 (5) | 0.058 (5) | 0.038 (3) | −0.001 (4) | −0.003 (3) | 0.001 (3) |
C2 | 0.057 (4) | 0.056 (5) | 0.055 (4) | 0.008 (4) | −0.006 (3) | 0.003 (4) |
C3 | 0.047 (4) | 0.053 (5) | 0.050 (4) | 0.005 (3) | 0.005 (3) | −0.006 (3) |
C4 | 0.039 (3) | 0.041 (3) | 0.044 (3) | −0.013 (3) | 0.000 (2) | −0.002 (3) |
C5 | 0.042 (3) | 0.033 (3) | 0.060 (4) | −0.003 (3) | 0.005 (3) | 0.001 (3) |
C6 | 0.063 (4) | 0.043 (4) | 0.052 (4) | −0.002 (4) | 0.014 (3) | −0.009 (3) |
C7 | 0.043 (3) | 0.047 (4) | 0.044 (3) | 0.000 (3) | 0.004 (3) | −0.002 (3) |
C8 | 0.052 (4) | 0.055 (5) | 0.040 (3) | −0.020 (3) | 0.002 (3) | 0.001 (3) |
C9 | 0.031 (3) | 0.037 (3) | 0.035 (3) | 0.006 (3) | 0.000 (2) | −0.001 (3) |
C10 | 0.037 (3) | 0.042 (3) | 0.037 (3) | 0.001 (3) | −0.001 (2) | −0.002 (3) |
C11 | 0.041 (3) | 0.055 (4) | 0.039 (3) | 0.000 (3) | −0.008 (3) | −0.002 (3) |
C12 | 0.039 (3) | 0.051 (4) | 0.046 (3) | 0.005 (3) | −0.008 (3) | 0.001 (3) |
C13 | 0.066 (4) | 0.067 (5) | 0.037 (3) | −0.009 (5) | −0.006 (3) | 0.005 (4) |
C14 | 0.042 (3) | 0.064 (5) | 0.043 (4) | 0.009 (4) | 0.001 (3) | −0.005 (4) |
Cl—C5 | 1.754 (7) | C3—C4 | 1.406 (10) |
S1—C9 | 1.742 (7) | C3—H3B | 0.9300 |
S1—C8 | 1.813 (6) | C4—C5 | 1.368 (9) |
S2—C9 | 1.738 (6) | C4—C7 | 1.514 (8) |
S2—C7 | 1.829 (7) | C5—C6 | 1.380 (10) |
N1—C11 | 1.139 (10) | C6—H6A | 0.9300 |
N2—C14 | 1.360 (9) | C7—C8 | 1.491 (9) |
N2—C12 | 1.369 (8) | C7—H7A | 0.9800 |
N2—C10 | 1.413 (8) | C8—H8A | 0.9700 |
N3—C14 | 1.267 (9) | C8—H8B | 0.9700 |
N3—C13 | 1.373 (11) | C9—C10 | 1.350 (9) |
C1—C6 | 1.361 (11) | C10—C11 | 1.433 (10) |
C1—C2 | 1.387 (11) | C12—C13 | 1.364 (10) |
C1—H1A | 0.9300 | C12—H12A | 0.9300 |
C2—C3 | 1.348 (10) | C13—H13A | 0.9300 |
C2—H2A | 0.9300 | C14—H14A | 0.9300 |
C9—S1—C8 | 96.2 (3) | C4—C7—S2 | 107.6 (5) |
C9—S2—C7 | 95.2 (3) | C8—C7—H7A | 108.5 |
C14—N2—C12 | 105.3 (5) | C4—C7—H7A | 108.5 |
C14—N2—C10 | 126.5 (5) | S2—C7—H7A | 108.5 |
C12—N2—C10 | 128.1 (5) | C7—C8—S1 | 108.7 (5) |
C14—N3—C13 | 105.1 (6) | C7—C8—H8A | 110.0 |
C6—C1—C2 | 118.8 (6) | S1—C8—H8A | 110.0 |
C6—C1—H1A | 120.6 | C7—C8—H8B | 110.0 |
C2—C1—H1A | 120.6 | S1—C8—H8B | 110.0 |
C3—C2—C1 | 120.8 (7) | H8A—C8—H8B | 108.3 |
C3—C2—H2A | 119.6 | C10—C9—S2 | 121.9 (5) |
C1—C2—H2A | 119.6 | C10—C9—S1 | 123.3 (5) |
C2—C3—C4 | 121.7 (7) | S2—C9—S1 | 114.8 (3) |
C2—C3—H3B | 119.1 | C9—C10—N2 | 121.7 (6) |
C4—C3—H3B | 119.1 | C9—C10—C11 | 120.7 (6) |
C5—C4—C3 | 116.1 (6) | N2—C10—C11 | 117.6 (6) |
C5—C4—C7 | 120.9 (6) | N1—C11—C10 | 178.6 (7) |
C3—C4—C7 | 123.0 (6) | C13—C12—N2 | 105.7 (6) |
C4—C5—C6 | 122.7 (7) | C13—C12—H12A | 127.2 |
C4—C5—Cl | 121.5 (5) | N2—C12—H12A | 127.2 |
C6—C5—Cl | 115.8 (6) | C12—C13—N3 | 109.9 (6) |
C1—C6—C5 | 119.9 (7) | C12—C13—H13A | 125.0 |
C1—C6—H6A | 120.1 | N3—C13—H13A | 125.0 |
C5—C6—H6A | 120.1 | N3—C14—N2 | 113.9 (7) |
C8—C7—C4 | 116.3 (5) | N3—C14—H14A | 123.0 |
C8—C7—S2 | 107.2 (5) | N2—C14—H14A | 123.0 |
C6—C1—C2—C3 | −0.3 (13) | C7—S2—C9—C10 | 162.9 (5) |
C1—C2—C3—C4 | −1.1 (13) | C7—S2—C9—S1 | −16.5 (4) |
C2—C3—C4—C5 | 1.8 (11) | C8—S1—C9—C10 | 175.6 (6) |
C2—C3—C4—C7 | 179.0 (7) | C8—S1—C9—S2 | −5.0 (4) |
C3—C4—C5—C6 | −1.3 (10) | S2—C9—C10—N2 | 173.5 (5) |
C7—C4—C5—C6 | −178.6 (7) | S1—C9—C10—N2 | −7.1 (9) |
C3—C4—C5—Cl | 178.9 (6) | S2—C9—C10—C11 | −4.9 (9) |
C7—C4—C5—Cl | 1.6 (9) | S1—C9—C10—C11 | 174.5 (5) |
C2—C1—C6—C5 | 0.8 (12) | C14—N2—C10—C9 | −74.5 (10) |
C4—C5—C6—C1 | 0.0 (12) | C12—N2—C10—C9 | 108.8 (8) |
Cl—C5—C6—C1 | 179.9 (6) | C14—N2—C10—C11 | 104.0 (8) |
C5—C4—C7—C8 | −137.7 (7) | C12—N2—C10—C11 | −72.7 (9) |
C3—C4—C7—C8 | 45.2 (10) | C14—N2—C12—C13 | 1.5 (8) |
C5—C4—C7—S2 | 102.1 (7) | C10—N2—C12—C13 | 178.7 (7) |
C3—C4—C7—S2 | −74.9 (7) | N2—C12—C13—N3 | −2.6 (9) |
C9—S2—C7—C8 | 37.4 (5) | C14—N3—C13—C12 | 2.7 (10) |
C9—S2—C7—C4 | 163.2 (4) | C13—N3—C14—N2 | −1.7 (10) |
C4—C7—C8—S1 | −165.6 (5) | C12—N2—C14—N3 | 0.2 (9) |
S2—C7—C8—S1 | −45.2 (6) | C10—N2—C14—N3 | −177.1 (7) |
C9—S1—C8—C7 | 31.2 (6) |