Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003168/wn6325sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003168/wn6325Isup2.hkl |
CCDC reference: 269882
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.035
- wR factor = 0.070
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C14 .. 5.47 su PLAT411_ALERT_2_C Short Inter H...H Contact H11 .. H15A .. 2.12 Ang.
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 27.50 From the CIF: _reflns_number_total 3833 Count of symmetry unique reflns 2251 Completeness (_total/calc) 170.28% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1582 Fraction of Friedel pairs measured 0.703 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: COLLECT (Bruker, 2002); cell refinement: EVALCCD (Bruker, 2002); data reduction: EVALCCD; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
C18H23NS2 | F(000) = 680 |
Mr = 317.51 | Dx = 1.228 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 313 reflections |
a = 9.908 (1) Å | θ = 6.0–20.0° |
b = 10.442 (1) Å | µ = 0.30 mm−1 |
c = 16.603 (2) Å | T = 100 K |
V = 1717.7 (3) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.28 × 0.23 mm |
Nonius KappaCCD diffractometer | 3833 independent reflections |
Radiation source: fine-focus sealed tube | 3274 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 3.8° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS (Bruke, 2002) | k = −13→13 |
Tmin = 0.913, Tmax = 0.932 | l = −21→21 |
19922 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Only H-atom coordinates refined |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.035P)2 + 0.237P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
3833 reflections | Δρmax = 0.23 e Å−3 |
259 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1582 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (6) |
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 | ||
S1 | 0.45286 (5) | 0.41208 (5) | 0.62524 (3) | 0.01864 (12) | |
S2 | 0.69472 (5) | 0.57059 (5) | 0.58026 (3) | 0.01942 (12) | |
N1 | 0.43437 (16) | 0.64939 (14) | 0.59824 (8) | 0.0112 (3) | |
C1 | 0.0345 (2) | 0.79692 (18) | 0.84925 (12) | 0.0178 (4) | |
C2 | −0.0181 (2) | 0.7691 (2) | 0.92461 (13) | 0.0234 (5) | |
C3 | −0.1370 (2) | 0.7012 (2) | 0.93226 (13) | 0.0249 (5) | |
C4 | −0.2038 (2) | 0.66116 (18) | 0.86351 (13) | 0.0213 (5) | |
C5 | −0.1510 (2) | 0.68747 (19) | 0.78731 (12) | 0.0174 (4) | |
C6 | −0.0298 (2) | 0.75477 (17) | 0.77960 (11) | 0.0134 (4) | |
C7 | 0.02838 (19) | 0.77699 (17) | 0.69622 (10) | 0.0120 (4) | |
C8 | −0.0513 (2) | 0.87778 (19) | 0.64958 (12) | 0.0173 (4) | |
C9 | 0.0497 (2) | 0.65266 (18) | 0.64576 (11) | 0.0140 (4) | |
C10 | 0.1836 (2) | 0.80113 (18) | 0.69050 (12) | 0.0134 (4) | |
C11 | 0.1894 (2) | 0.70377 (17) | 0.61921 (11) | 0.0131 (4) | |
C12 | 0.30238 (19) | 0.60965 (17) | 0.61674 (10) | 0.0131 (4) | |
C13 | 0.2958 (2) | 0.48380 (18) | 0.63185 (12) | 0.0170 (4) | |
C14 | 0.5298 (2) | 0.55566 (18) | 0.60017 (10) | 0.0147 (4) | |
C15 | 0.4687 (2) | 0.77987 (18) | 0.57230 (11) | 0.0133 (4) | |
C16 | 0.5265 (2) | 0.86537 (18) | 0.63842 (12) | 0.0144 (4) | |
C17 | 0.5728 (2) | 0.99118 (19) | 0.60051 (13) | 0.0184 (4) | |
C18 | 0.6214 (2) | 1.0885 (2) | 0.66237 (15) | 0.0257 (5) | |
H1 | 0.113 (3) | 0.839 (2) | 0.8443 (15) | 0.040* | |
H2 | 0.026 (3) | 0.796 (2) | 0.9684 (15) | 0.040* | |
H3 | −0.167 (3) | 0.681 (2) | 0.9898 (15) | 0.040* | |
H4 | −0.283 (3) | 0.617 (2) | 0.8681 (15) | 0.040* | |
H5 | −0.198 (3) | 0.655 (2) | 0.7381 (16) | 0.040* | |
H8A | −0.043 (3) | 0.961 (3) | 0.6768 (15) | 0.040* | |
H8B | −0.145 (3) | 0.848 (2) | 0.6389 (16) | 0.040* | |
H8C | −0.018 (3) | 0.893 (2) | 0.5965 (16) | 0.040* | |
H9A | −0.020 (3) | 0.638 (2) | 0.6030 (15) | 0.040* | |
H9B | 0.061 (3) | 0.574 (3) | 0.6805 (14) | 0.040* | |
H10A | 0.208 (3) | 0.888 (3) | 0.6764 (15) | 0.040* | |
H10B | 0.232 (3) | 0.766 (2) | 0.7364 (15) | 0.040* | |
H11 | 0.180 (3) | 0.752 (2) | 0.5642 (15) | 0.040* | |
H13 | 0.216 (3) | 0.437 (2) | 0.6438 (15) | 0.040* | |
H15A | 0.536 (3) | 0.774 (2) | 0.5284 (14) | 0.040* | |
H15B | 0.383 (3) | 0.819 (2) | 0.5490 (15) | 0.040* | |
H16A | 0.601 (3) | 0.822 (2) | 0.6625 (15) | 0.040* | |
H16B | 0.453 (3) | 0.884 (2) | 0.6818 (15) | 0.040* | |
H17A | 0.645 (3) | 0.977 (2) | 0.5612 (16) | 0.040* | |
H17B | 0.496 (3) | 1.027 (2) | 0.5697 (15) | 0.040* | |
H18A | 0.551 (3) | 1.112 (2) | 0.7044 (15) | 0.040* | |
H18B | 0.690 (3) | 1.059 (3) | 0.6915 (16) | 0.040* | |
H18C | 0.653 (3) | 1.162 (3) | 0.6364 (16) | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0182 (2) | 0.0123 (2) | 0.0254 (3) | 0.0017 (2) | 0.0042 (2) | −0.0008 (2) |
S2 | 0.0109 (2) | 0.0229 (3) | 0.0245 (3) | 0.0015 (2) | 0.0004 (2) | −0.0036 (2) |
N1 | 0.0090 (8) | 0.0137 (7) | 0.0110 (7) | −0.0004 (7) | 0.0010 (6) | −0.0002 (6) |
C1 | 0.0168 (11) | 0.0156 (10) | 0.0211 (10) | 0.0046 (9) | 0.0001 (9) | −0.0014 (7) |
C2 | 0.0308 (13) | 0.0236 (10) | 0.0156 (10) | 0.0103 (10) | −0.0029 (9) | −0.0025 (9) |
C3 | 0.0372 (14) | 0.0183 (11) | 0.0193 (11) | 0.0100 (10) | 0.0100 (10) | 0.0048 (8) |
C4 | 0.0232 (11) | 0.0120 (9) | 0.0287 (12) | 0.0021 (9) | 0.0101 (10) | 0.0007 (8) |
C5 | 0.0189 (11) | 0.0115 (9) | 0.0217 (11) | 0.0019 (8) | 0.0037 (8) | −0.0022 (8) |
C6 | 0.0127 (10) | 0.0089 (9) | 0.0187 (10) | 0.0048 (8) | 0.0006 (8) | −0.0003 (7) |
C7 | 0.0088 (9) | 0.0124 (9) | 0.0148 (9) | 0.0000 (8) | 0.0006 (7) | −0.0005 (7) |
C8 | 0.0142 (11) | 0.0187 (10) | 0.0189 (10) | 0.0052 (9) | −0.0001 (9) | 0.0024 (7) |
C9 | 0.0110 (9) | 0.0154 (9) | 0.0157 (9) | −0.0019 (9) | 0.0013 (8) | 0.0000 (7) |
C10 | 0.0096 (9) | 0.0122 (9) | 0.0182 (10) | −0.0001 (9) | 0.0000 (8) | −0.0023 (7) |
C11 | 0.0116 (9) | 0.0136 (9) | 0.0142 (9) | −0.0003 (8) | 0.0016 (8) | 0.0000 (7) |
C12 | 0.0112 (9) | 0.0183 (10) | 0.0098 (8) | −0.0033 (8) | 0.0013 (8) | −0.0019 (7) |
C13 | 0.0155 (10) | 0.0149 (9) | 0.0205 (10) | −0.0004 (9) | 0.0048 (9) | −0.0029 (8) |
C14 | 0.0154 (10) | 0.0175 (9) | 0.0111 (9) | −0.0018 (9) | 0.0000 (7) | −0.0045 (7) |
C15 | 0.0130 (10) | 0.0152 (9) | 0.0118 (9) | −0.0024 (9) | 0.0014 (8) | 0.0012 (7) |
C16 | 0.0119 (10) | 0.0156 (9) | 0.0156 (10) | −0.0007 (8) | −0.0016 (8) | −0.0007 (7) |
C17 | 0.0178 (11) | 0.0154 (10) | 0.0221 (11) | −0.0022 (8) | −0.0007 (8) | 0.0016 (8) |
C18 | 0.0239 (12) | 0.0154 (11) | 0.0376 (14) | −0.0008 (11) | −0.0067 (10) | −0.0015 (10) |
S1—C13 | 1.731 (2) | C8—H8C | 0.95 (3) |
S1—C14 | 1.733 (2) | C9—C11 | 1.548 (3) |
S2—C14 | 1.675 (2) | C9—H9A | 1.00 (3) |
N1—C14 | 1.361 (2) | C9—H9B | 1.01 (3) |
N1—C12 | 1.406 (2) | C10—C11 | 1.561 (2) |
N1—C15 | 1.469 (2) | C10—H10A | 0.97 (3) |
C1—C2 | 1.386 (3) | C10—H10B | 0.97 (3) |
C1—C6 | 1.392 (3) | C11—C12 | 1.490 (3) |
C1—H1 | 0.89 (3) | C11—H11 | 1.04 (2) |
C2—C3 | 1.381 (3) | C12—C13 | 1.339 (3) |
C2—H2 | 0.89 (3) | C13—H13 | 0.95 (3) |
C3—C4 | 1.384 (3) | C15—C16 | 1.527 (3) |
C3—H3 | 1.02 (3) | C15—H15A | 0.99 (3) |
C4—C5 | 1.396 (3) | C15—H15B | 1.02 (3) |
C4—H4 | 0.92 (3) | C16—C17 | 1.527 (3) |
C5—C6 | 1.397 (3) | C16—H16A | 0.95 (3) |
C5—H5 | 1.00 (3) | C16—H16B | 1.04 (3) |
C6—C7 | 1.518 (2) | C17—C18 | 1.524 (3) |
C7—C8 | 1.527 (3) | C17—H17A | 0.98 (3) |
C7—C9 | 1.560 (2) | C17—H17B | 0.99 (3) |
C7—C10 | 1.561 (3) | C18—H18A | 1.02 (3) |
C8—H8A | 0.98 (3) | C18—H18B | 0.89 (3) |
C8—H8B | 1.00 (3) | C18—H18C | 0.93 (3) |
C13—S1—C14 | 92.08 (9) | C7—C10—H10B | 112.3 (15) |
C14—N1—C12 | 115.38 (15) | C11—C10—H10B | 109.2 (15) |
C14—N1—C15 | 120.86 (15) | H10A—C10—H10B | 115 (2) |
C12—N1—C15 | 123.60 (15) | C12—C11—C9 | 116.88 (16) |
C2—C1—C6 | 120.7 (2) | C12—C11—C10 | 118.57 (17) |
C2—C1—H1 | 120.8 (17) | C9—C11—C10 | 88.59 (14) |
C6—C1—H1 | 118.4 (17) | C12—C11—H11 | 111.1 (14) |
C3—C2—C1 | 120.8 (2) | C9—C11—H11 | 109.4 (15) |
C3—C2—H2 | 120.1 (17) | C10—C11—H11 | 110.3 (14) |
C1—C2—H2 | 119.1 (17) | C13—C12—N1 | 112.09 (17) |
C2—C3—C4 | 119.2 (2) | C13—C12—C11 | 127.24 (18) |
C2—C3—H3 | 115.9 (15) | N1—C12—C11 | 120.66 (16) |
C4—C3—H3 | 124.9 (15) | C12—C13—S1 | 111.63 (16) |
C3—C4—C5 | 120.6 (2) | C12—C13—H13 | 125.7 (15) |
C3—C4—H4 | 119.7 (16) | S1—C13—H13 | 122.7 (15) |
C5—C4—H4 | 119.8 (16) | N1—C14—S2 | 127.32 (14) |
C4—C5—C6 | 120.3 (2) | N1—C14—S1 | 108.82 (13) |
C4—C5—H5 | 119.9 (16) | S2—C14—S1 | 123.86 (12) |
C6—C5—H5 | 119.7 (16) | N1—C15—C16 | 114.74 (15) |
C1—C6—C5 | 118.46 (18) | N1—C15—H15A | 108.3 (15) |
C1—C6—C7 | 122.38 (18) | C16—C15—H15A | 108.4 (15) |
C5—C6—C7 | 119.15 (16) | N1—C15—H15B | 106.6 (14) |
C6—C7—C8 | 111.81 (16) | C16—C15—H15B | 110.8 (15) |
C6—C7—C9 | 114.48 (15) | H15A—C15—H15B | 107.8 (19) |
C8—C7—C9 | 111.81 (15) | C15—C16—C17 | 108.61 (16) |
C6—C7—C10 | 117.03 (16) | C15—C16—H16A | 108.2 (15) |
C8—C7—C10 | 111.56 (16) | C17—C16—H16A | 110.7 (16) |
C9—C7—C10 | 88.18 (14) | C15—C16—H16B | 109.8 (14) |
C7—C8—H8A | 109.2 (15) | C17—C16—H16B | 109.8 (13) |
C7—C8—H8B | 111.0 (15) | H16A—C16—H16B | 110 (2) |
H8A—C8—H8B | 116 (2) | C18—C17—C16 | 113.02 (18) |
C7—C8—H8C | 114.0 (15) | C18—C17—H17A | 108.6 (15) |
H8A—C8—H8C | 104 (2) | C16—C17—H17A | 111.1 (16) |
H8B—C8—H8C | 102 (2) | C18—C17—H17B | 109.9 (15) |
C11—C9—C7 | 89.27 (14) | C16—C17—H17B | 107.8 (15) |
C11—C9—H9A | 118.0 (14) | H17A—C17—H17B | 106 (2) |
C7—C9—H9A | 114.5 (14) | C17—C18—H18A | 114.0 (14) |
C11—C9—H9B | 109.9 (15) | C17—C18—H18B | 112.0 (17) |
C7—C9—H9B | 112.6 (14) | H18A—C18—H18B | 104 (2) |
H9A—C9—H9B | 111 (2) | C17—C18—H18C | 110.1 (16) |
C7—C10—C11 | 88.71 (14) | H18A—C18—H18C | 110 (2) |
C7—C10—H10A | 114.5 (16) | H18B—C18—H18C | 106 (2) |
C11—C10—H10A | 114.7 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···S2 | 0.99 (3) | 2.78 (2) | 3.132 (2) | 102 (2) |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register