Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025286/ci6627sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025286/ci6627Isup2.hkl |
CCDC reference: 283775
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.062
- wR factor = 0.142
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.420 From the CIF: _refine_ls_abs_structure_Flack_su 0.110 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.42 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT731_ALERT_1_C Bond Calc 0.88(4), Rep 0.876(10) ...... 4.00 su-Rat N1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.88(4), Rep 0.880(10) ...... 4.00 su-Rat N1 -H1 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.37 From the CIF: _reflns_number_total 3021 Count of symmetry unique reflns 1737 Completeness (_total/calc) 173.92% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1284 Fraction of Friedel pairs measured 0.739 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).
C15H11ClN2S | Dx = 1.317 Mg m−3 |
Mr = 286.77 | Melting point: 489 K |
Orthorhombic, Pnc2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 -2bc | Cell parameters from 1456 reflections |
a = 9.993 (2) Å | θ = 5–35° |
b = 14.223 (3) Å | µ = 0.40 mm−1 |
c = 10.175 (2) Å | T = 293 K |
V = 1446.2 (5) Å3 | Thin-plate, colourless |
Z = 4 | 0.5 × 0.3 × 0.08 mm |
F(000) = 592 |
Bruker SMART CCD area-detector diffractometer | 3021 independent reflections |
Radiation source: fine-focus sealed tube | 1505 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.057 |
ω scans | θmax = 27.4°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→12 |
Tmin = 0.865, Tmax = 0.972 | k = −18→17 |
10960 measured reflections | l = −13→13 |
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)] = 0.062 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.142 | w = 1/[σ2(Fo2) + (0.0619P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3021 reflections | Δρmax = 0.25 e Å−3 |
175 parameters | Δρmin = −0.15 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1358 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.42 (11) |
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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = 0.13757(0.00154) m2 = -0.98122(0.00042) m3 = -0.13522(0.00196) D = -9.08012(0.00790) Atom d s d/s (d/s)**2 C9 * -0.0215 0.0040 - 5.369 28.824 C10 * 0.0152 0.0037 4.079 16.637 C11 * 0.0148 0.0047 3.143 9.879 C12 * -0.0059 0.0057 - 1.026 1.052 C13 * -0.0214 0.0055 - 3.918 15.354 C14 * -0.0078 0.0049 - 1.580 2.496 C15 * 0.0147 0.0043 3.424 11.723 C5 0.7465 0.0040 186.903 34932.703 N2 - 0.7383 0.0041 - 179.810 32331.744 ============ Sum((d/s)**2) for starred atoms 85.965 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity Plane 2 m1 = 0.78728(0.00048) m2 = 0.59107(0.00043) m3 = -0.17559(0.00138) D = 6.05288(0.00355) Atom d s d/s (d/s)**2 Cl1 * 0.0054 0.0017 3.233 10.454 C1 * -0.0144 0.0046 - 3.146 9.895 C2 * -0.0202 0.0051 - 3.948 15.590 C3 * -0.0127 0.0049 - 2.616 6.842 C4 * -0.0238 0.0042 - 5.672 32.169 C5 * -0.0219 0.0038 - 5.705 32.544 C6 * 0.0001 0.0040 0.031 0.001 N1 * 0.0344 0.0036 9.608 92.312 C9 * 0.0042 0.0044 0.959 0.920 C7 - 0.6012 0.0043 - 138.282 19121.834 C10 0.7792 0.0042 183.675 33736.688 ============ Sum((d/s)**2) for starred atoms 200.726 Chi-squared at 95% for 6 degrees of freedom: 12.60 The group of atoms deviates significantly from planarity Plane 3 m1 = -0.73679(0.00197) m2 = -0.46525(0.00490) m3 = -0.49060(0.00611) D = -5.88482(0.03869) Atom d s d/s (d/s)**2 C4 * 0.0000 0.0044 0.002 0.000 N1 * 0.0000 0.0036 - 0.006 0.000 C7 * 0.0000 0.0044 0.002 0.000 H1 * 0.0010 0.0382 0.025 0.001 S1 - 0.0509 0.0016 - 31.624 1000.085 C3 0.7619 0.0048 157.498 24805.602 ============ Sum((d/s)**2) for starred atoms 0.001 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms does not deviate significantly from planarity Plane 4 m1 = -0.40906(0.00619) m2 = 0.69283(0.00489) m3 = 0.59385(0.00241) D = 8.93762(0.04243) Atom d s d/s (d/s)**2 C8 * 0.0000 0.0053 0.000 0.000 N2 * 0.0000 0.0038 0.000 0.000 C7 * 0.0000 0.0049 0.000 0.000 C9 - 1.0832 0.0042 - 255.959 65514.773 N1 - 1.1572 0.0036 - 324.511 105307.344 ============ Sum((d/s)**2) for starred atoms 0.000 Plane 5 m1 = -0.48854(0.00252) m2 = -0.86124(0.00127) m3 = -0.13997(0.00202) D = -9.19395(0.01436) Atom d s d/s (d/s)**2 N1 * 0.0046 0.0036 1.276 1.628 N2 * 0.0073 0.0040 1.833 3.360 C7 * -0.0103 0.0048 - 2.127 4.523 C9 * -0.0065 0.0041 - 1.562 2.441 C8 0.7519 0.0053 143.126 20484.998 C4 0.6376 0.0042 153.217 23475.359 ============ Sum((d/s)**2) for starred atoms 11.952 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Plane 6 m1 = 0.80468(0.00133) m2 = 0.56282(0.00234) m3 = -0.18901(0.00245) D = 5.78553(0.02423) Atom d s d/s (d/s)**2 C4 * -0.0078 0.0042 - 1.851 3.426 C5 * 0.0063 0.0038 1.648 2.717 N1 * 0.0027 0.0036 0.757 0.573 C9 * -0.0039 0.0044 - 0.885 0.783 C7 - 0.6704 0.0043 - 155.555 24197.275 N2 - 0.6699 0.0038 - 177.590 31538.049 ============ Sum((d/s)**2) for starred atoms 7.499 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates significantly from planarity Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 63.39 (0.09) 116.61 (0.09) 1 3 65.07 (0.26) 114.93 (0.26) 1 4 35.28 (0.28) 144.72 (0.28) 1 5 37.18 (0.16) 142.82 (0.16) 1 6 65.42 (0.13) 114.58 (0.13) 2 3 39.74 (1/3) 140.26 (1/3) 2 4 89.04 (0.31) 90.96 (0.31) 2 5 29.65 (0.14) 150.35 (0.14) 2 6 2.05 (0.13) 177.95 (0.13) 3 4 71.80 (0.40) 108.20 (0.40) 3 5 33.97 (0.31) 146.03 (0.31) 3 6 40.36 (1/3) 139.64 (1/3) 4 5 61.32 (0.36) 118.68 (0.36) 4 6 87.05 (0.34) 92.95 (0.34) 5 6 31.64 (0.18) 148.36 (0.18) |
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 | ||
Cl1 | 0.39074 (18) | 0.37536 (10) | 0.09580 (18) | 0.1276 (7) | |
S1 | −0.11734 (13) | 0.83597 (14) | 0.25400 (18) | 0.1197 (7) | |
N1 | 0.0504 (4) | 0.7113 (3) | 0.1617 (4) | 0.0696 (10) | |
H1 | 0.060 (4) | 0.750 (3) | 0.095 (3) | 0.084* | |
N2 | 0.0777 (4) | 0.6675 (3) | 0.4431 (4) | 0.0742 (11) | |
C1 | 0.2895 (5) | 0.4731 (3) | 0.1211 (6) | 0.0819 (14) | |
C2 | 0.2234 (5) | 0.5114 (4) | 0.0133 (6) | 0.0906 (15) | |
H2 | 0.2322 | 0.4844 | −0.0695 | 0.109* | |
C3 | 0.1448 (5) | 0.5896 (4) | 0.0311 (5) | 0.0805 (14) | |
H3 | 0.1016 | 0.6163 | −0.0407 | 0.097* | |
C4 | 0.1292 (4) | 0.6291 (3) | 0.1544 (5) | 0.0627 (12) | |
C5 | 0.1954 (4) | 0.5905 (3) | 0.2631 (5) | 0.0609 (11) | |
C6 | 0.2774 (4) | 0.5118 (3) | 0.2418 (5) | 0.0704 (12) | |
H6 | 0.3242 | 0.4859 | 0.3120 | 0.085* | |
C7 | −0.0352 (4) | 0.7357 (4) | 0.2555 (5) | 0.0792 (13) | |
C8 | −0.0448 (4) | 0.6646 (4) | 0.3649 (5) | 0.0907 (15) | |
H8A | −0.1213 | 0.6788 | 0.4202 | 0.109* | |
H8B | −0.0570 | 0.6022 | 0.3284 | 0.109* | |
C9 | 0.1850 (5) | 0.6314 (3) | 0.3953 (4) | 0.0592 (11) | |
C10 | 0.3036 (5) | 0.6316 (3) | 0.4850 (5) | 0.0613 (11) | |
C11 | 0.2872 (5) | 0.6170 (3) | 0.6174 (5) | 0.0831 (14) | |
H11 | 0.2026 | 0.6044 | 0.6510 | 0.100* | |
C12 | 0.3960 (7) | 0.6210 (4) | 0.7009 (6) | 0.1040 (19) | |
H12 | 0.3840 | 0.6112 | 0.7904 | 0.125* | |
C13 | 0.5212 (7) | 0.6391 (4) | 0.6531 (7) | 0.1033 (19) | |
H13 | 0.5939 | 0.6421 | 0.7101 | 0.124* | |
C14 | 0.5389 (5) | 0.6528 (3) | 0.5224 (7) | 0.0898 (17) | |
H14 | 0.6242 | 0.6648 | 0.4897 | 0.108* | |
C15 | 0.4302 (4) | 0.6489 (3) | 0.4364 (5) | 0.0744 (14) | |
H15 | 0.4430 | 0.6580 | 0.3467 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1550 (15) | 0.0789 (8) | 0.1490 (15) | 0.0358 (8) | −0.0427 (12) | −0.0419 (10) |
S1 | 0.0824 (9) | 0.1687 (15) | 0.1078 (12) | 0.0567 (9) | −0.0141 (10) | −0.0419 (12) |
N1 | 0.059 (2) | 0.085 (3) | 0.065 (2) | 0.007 (2) | −0.004 (2) | −0.0088 (19) |
N2 | 0.051 (2) | 0.111 (3) | 0.061 (2) | −0.017 (2) | 0.003 (2) | 0.000 (2) |
C1 | 0.081 (3) | 0.062 (3) | 0.103 (4) | −0.002 (2) | −0.021 (3) | −0.019 (3) |
C2 | 0.101 (4) | 0.081 (3) | 0.089 (4) | 0.008 (3) | −0.010 (3) | −0.037 (3) |
C3 | 0.086 (4) | 0.081 (3) | 0.075 (4) | 0.011 (3) | −0.013 (3) | −0.020 (3) |
C4 | 0.058 (3) | 0.060 (3) | 0.070 (3) | −0.004 (2) | −0.002 (2) | −0.012 (2) |
C5 | 0.055 (3) | 0.058 (3) | 0.070 (3) | −0.019 (2) | −0.007 (3) | 0.001 (2) |
C6 | 0.075 (3) | 0.054 (3) | 0.082 (3) | −0.010 (2) | −0.018 (3) | −0.008 (3) |
C7 | 0.043 (2) | 0.132 (4) | 0.064 (3) | 0.002 (3) | −0.011 (3) | −0.023 (3) |
C8 | 0.043 (3) | 0.151 (4) | 0.078 (4) | −0.022 (3) | 0.001 (3) | −0.013 (4) |
C9 | 0.051 (3) | 0.070 (3) | 0.057 (3) | −0.020 (2) | 0.001 (3) | 0.003 (2) |
C10 | 0.056 (3) | 0.057 (2) | 0.072 (3) | −0.0102 (19) | −0.007 (3) | −0.002 (2) |
C11 | 0.074 (3) | 0.100 (3) | 0.075 (4) | −0.006 (3) | −0.008 (3) | 0.012 (3) |
C12 | 0.103 (5) | 0.127 (5) | 0.083 (4) | 0.003 (4) | −0.033 (4) | 0.006 (4) |
C13 | 0.088 (5) | 0.100 (4) | 0.123 (6) | 0.009 (3) | −0.039 (5) | −0.021 (4) |
C14 | 0.060 (3) | 0.080 (3) | 0.129 (6) | −0.005 (3) | −0.010 (4) | −0.026 (4) |
C15 | 0.055 (3) | 0.076 (3) | 0.092 (4) | −0.007 (2) | 0.002 (3) | −0.020 (3) |
Cl1—C1 | 1.738 (5) | C6—H6 | 0.93 |
S1—C7 | 1.645 (5) | C7—C8 | 1.507 (7) |
N1—C7 | 1.328 (5) | C8—H8A | 0.97 |
N1—C4 | 1.413 (5) | C8—H8B | 0.97 |
N1—H1 | 0.876 (10) | C9—C10 | 1.496 (6) |
N2—C9 | 1.284 (5) | C10—C11 | 1.373 (6) |
N2—C8 | 1.460 (5) | C10—C15 | 1.380 (6) |
C1—C6 | 1.352 (6) | C11—C12 | 1.380 (7) |
C1—C2 | 1.391 (6) | C11—H11 | 0.93 |
C2—C3 | 1.373 (7) | C12—C13 | 1.366 (7) |
C2—H2 | 0.93 | C12—H12 | 0.93 |
C3—C4 | 1.383 (6) | C13—C14 | 1.356 (8) |
C3—H3 | 0.93 | C13—H13 | 0.93 |
C4—C5 | 1.401 (6) | C14—C15 | 1.396 (7) |
C5—C6 | 1.403 (6) | C14—H14 | 0.93 |
C5—C9 | 1.469 (6) | C15—H15 | 0.93 |
C7—N1—C4 | 127.8 (4) | N2—C8—H8A | 109.8 |
C7—N1—H1 | 117 (3) | C7—C8—H8A | 109.8 |
C4—N1—H1 | 115 (3) | N2—C8—H8B | 109.8 |
C9—N2—C8 | 118.8 (4) | C7—C8—H8B | 109.8 |
C6—C1—C2 | 121.0 (4) | H8A—C8—H8B | 108.3 |
C6—C1—Cl1 | 120.8 (4) | N2—C9—C5 | 124.4 (4) |
C2—C1—Cl1 | 118.2 (4) | N2—C9—C10 | 115.4 (4) |
C3—C2—C1 | 119.0 (5) | C5—C9—C10 | 120.2 (4) |
C3—C2—H2 | 120.5 | C11—C10—C15 | 119.2 (4) |
C1—C2—H2 | 120.5 | C11—C10—C9 | 120.3 (4) |
C2—C3—C4 | 120.9 (5) | C15—C10—C9 | 120.5 (4) |
C2—C3—H3 | 119.6 | C10—C11—C12 | 120.2 (5) |
C4—C3—H3 | 119.6 | C10—C11—H11 | 119.9 |
C3—C4—C5 | 120.2 (4) | C12—C11—H11 | 119.9 |
C3—C4—N1 | 116.5 (4) | C13—C12—C11 | 120.7 (6) |
C5—C4—N1 | 123.1 (4) | C13—C12—H12 | 119.7 |
C4—C5—C6 | 117.8 (4) | C11—C12—H12 | 119.7 |
C4—C5—C9 | 122.3 (4) | C14—C13—C12 | 119.7 (6) |
C6—C5—C9 | 119.9 (4) | C14—C13—H13 | 120.2 |
C1—C6—C5 | 121.2 (4) | C12—C13—H13 | 120.2 |
C1—C6—H6 | 119.4 | C13—C14—C15 | 120.5 (6) |
C5—C6—H6 | 119.4 | C13—C14—H14 | 119.8 |
N1—C7—C8 | 113.4 (4) | C15—C14—H14 | 119.8 |
N1—C7—S1 | 122.8 (4) | C10—C15—C14 | 119.7 (5) |
C8—C7—S1 | 123.8 (4) | C10—C15—H15 | 120.2 |
N2—C8—C7 | 109.3 (3) | C14—C15—H15 | 120.2 |
C6—C1—C2—C3 | −0.1 (7) | S1—C7—C8—N2 | −105.9 (4) |
Cl1—C1—C2—C3 | −178.9 (4) | C8—N2—C9—C5 | 2.9 (6) |
C1—C2—C3—C4 | −1.2 (7) | C8—N2—C9—C10 | −176.1 (4) |
C2—C3—C4—C5 | 1.0 (7) | C4—C5—C9—N2 | 37.6 (6) |
C2—C3—C4—N1 | 177.8 (4) | C6—C5—C9—N2 | −144.5 (4) |
C7—N1—C4—C3 | 142.0 (4) | C4—C5—C9—C10 | −143.4 (4) |
C7—N1—C4—C5 | −41.3 (6) | C6—C5—C9—C10 | 34.4 (5) |
C3—C4—C5—C6 | 0.4 (6) | N2—C9—C10—C11 | 36.5 (6) |
N1—C4—C5—C6 | −176.1 (3) | C5—C9—C10—C11 | −142.6 (4) |
C3—C4—C5—C9 | 178.3 (4) | N2—C9—C10—C15 | −141.8 (4) |
N1—C4—C5—C9 | 1.7 (6) | C5—C9—C10—C15 | 39.1 (6) |
C2—C1—C6—C5 | 1.5 (7) | C15—C10—C11—C12 | 0.9 (7) |
Cl1—C1—C6—C5 | −179.7 (3) | C9—C10—C11—C12 | −177.4 (4) |
C4—C5—C6—C1 | −1.6 (6) | C10—C11—C12—C13 | −0.2 (8) |
C9—C5—C6—C1 | −179.6 (4) | C11—C12—C13—C14 | −0.4 (9) |
C4—N1—C7—C8 | 0.2 (6) | C12—C13—C14—C15 | 0.4 (8) |
C4—N1—C7—S1 | 177.9 (3) | C11—C10—C15—C14 | −1.0 (7) |
C9—N2—C8—C7 | −74.3 (5) | C9—C10—C15—C14 | 177.3 (4) |
N1—C7—C8—N2 | 71.7 (5) | C13—C14—C15—C10 | 0.4 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N2i | 0.88 (1) | 1.95 (3) | 2.827 (5) | 177 (3) |
Symmetry code: (i) x, −y+3/2, z−1/2. |
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