Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025376/cf6299sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025376/cf6299Isup2.hkl |
CCDC reference: 227887
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).
C16H22N4S2 | Dx = 1.196 Mg m−3 |
Mr = 334.50 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 7087 reflections |
a = 9.5897 (6) Å | θ = 2.1–25.8° |
b = 27.024 (2) Å | µ = 0.29 mm−1 |
c = 14.3392 (14) Å | T = 293 K |
V = 3716.1 (5) Å3 | Lath, pale yellow |
Z = 8 | 0.80 × 0.34 × 0.08 mm |
F(000) = 1424 |
Stoe IPDS2 diffractometer | 4367 independent reflections |
Radiation source: fine-focus sealed tube | 1651 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.092 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.8°, θmin = 2.1° |
ω scans | h = −12→11 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −35→35 |
Tmin = 0.802, Tmax = 0.977 | l = −18→18 |
26348 measured reflections |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 0.72 | w = 1/[σ2(Fo2) + (0.0239P)2] where P = (Fo2 + 2Fc2)/3 |
4367 reflections | (Δ/σ)max = 0.001 |
199 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Experimental. Because the crystal collected datas is very thin, check cif give B type allert "Ratio Observed / Unique Reflections too Low ···. 38 Perc." |
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 | ||
C11 | 0.3186 (4) | 0.80482 (13) | 0.9447 (2) | 0.0911 (12) | |
H11A | 0.4145 | 0.8148 | 0.9405 | 0.137* | |
H11B | 0.3099 | 0.7783 | 0.9889 | 0.137* | |
H11C | 0.2629 | 0.8324 | 0.9647 | 0.137* | |
C12 | 0.2940 (4) | 0.82653 (12) | 0.7845 (3) | 0.0960 (12) | |
H12A | 0.3908 | 0.8356 | 0.7843 | 0.144* | |
H12B | 0.2384 | 0.8550 | 0.7996 | 0.144* | |
H12C | 0.2681 | 0.8144 | 0.7240 | 0.144* | |
S1 | 0.20135 (7) | 0.69814 (3) | 0.74335 (6) | 0.0584 (2) | |
S2 | 0.34219 (8) | 0.60427 (3) | 0.68672 (6) | 0.0618 (2) | |
C5 | 0.1821 (2) | 0.61723 (9) | 0.63474 (18) | 0.0425 (6) | |
C7 | −0.0070 (3) | 0.67568 (9) | 0.61607 (19) | 0.0466 (7) | |
H7 | −0.0482 | 0.7058 | 0.6308 | 0.056* | |
C6 | 0.1154 (2) | 0.66256 (9) | 0.65893 (18) | 0.0413 (6) | |
C3 | −0.0076 (3) | 0.59941 (10) | 0.52946 (19) | 0.0467 (7) | |
C8 | −0.0710 (3) | 0.64504 (10) | 0.55123 (19) | 0.0458 (7) | |
C4 | 0.1152 (3) | 0.58654 (9) | 0.5711 (2) | 0.0479 (7) | |
H4 | 0.1555 | 0.5562 | 0.5563 | 0.057* | |
C2 | −0.0721 (3) | 0.56667 (11) | 0.4639 (2) | 0.0597 (8) | |
C14 | 0.5352 (3) | 0.53291 (11) | 0.6702 (2) | 0.0665 (9) | |
H14A | 0.5998 | 0.5604 | 0.6656 | 0.080* | |
H14B | 0.5229 | 0.5251 | 0.7357 | 0.080* | |
N3 | 0.2706 (2) | 0.78811 (8) | 0.85361 (18) | 0.0585 (7) | |
N4 | 0.5934 (3) | 0.48997 (10) | 0.62194 (17) | 0.0669 (7) | |
C1 | −0.1962 (3) | 0.65976 (11) | 0.5059 (2) | 0.0619 (8) | |
C10 | 0.1271 (3) | 0.77267 (11) | 0.8570 (2) | 0.0672 (9) | |
H10A | 0.0687 | 0.8014 | 0.8684 | 0.081* | |
H10B | 0.1147 | 0.7500 | 0.9087 | 0.081* | |
C9 | 0.0794 (3) | 0.74742 (11) | 0.7672 (2) | 0.0673 (9) | |
H9A | 0.0783 | 0.7709 | 0.7162 | 0.081* | |
H9B | −0.0139 | 0.7342 | 0.7749 | 0.081* | |
N2 | −0.1223 (3) | 0.54044 (10) | 0.4114 (2) | 0.0855 (9) | |
C13 | 0.3970 (3) | 0.54765 (10) | 0.6288 (2) | 0.0610 (8) | |
H13A | 0.3287 | 0.5217 | 0.6387 | 0.073* | |
H13B | 0.4064 | 0.5532 | 0.5623 | 0.073* | |
N1 | −0.2961 (3) | 0.67096 (12) | 0.4685 (2) | 0.1016 (11) | |
C16 | 0.7342 (3) | 0.48091 (14) | 0.6532 (3) | 0.0896 (12) | |
H16A | 0.7715 | 0.4528 | 0.6208 | 0.134* | |
H16B | 0.7339 | 0.4745 | 0.7190 | 0.134* | |
H16C | 0.7907 | 0.5094 | 0.6405 | 0.134* | |
C15 | 0.5080 (4) | 0.44650 (12) | 0.6367 (3) | 0.0959 (12) | |
H15A | 0.5480 | 0.4189 | 0.6041 | 0.144* | |
H15B | 0.4156 | 0.4526 | 0.6136 | 0.144* | |
H15C | 0.5038 | 0.4392 | 0.7022 | 0.144* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.087 (3) | 0.094 (3) | 0.093 (3) | 0.003 (2) | −0.018 (2) | −0.044 (2) |
C12 | 0.116 (3) | 0.067 (2) | 0.105 (3) | −0.010 (2) | 0.007 (3) | −0.012 (2) |
S1 | 0.0484 (4) | 0.0530 (4) | 0.0738 (5) | 0.0067 (3) | −0.0146 (4) | −0.0246 (4) |
S2 | 0.0572 (4) | 0.0491 (4) | 0.0790 (6) | 0.0095 (4) | −0.0210 (4) | −0.0179 (4) |
C5 | 0.0432 (16) | 0.0427 (14) | 0.0417 (16) | −0.0045 (12) | −0.0015 (13) | −0.0007 (12) |
C7 | 0.0470 (16) | 0.0407 (14) | 0.0520 (18) | 0.0023 (13) | −0.0001 (15) | −0.0066 (13) |
C6 | 0.0395 (15) | 0.0377 (14) | 0.0466 (17) | −0.0019 (12) | 0.0016 (13) | −0.0044 (12) |
C3 | 0.0449 (16) | 0.0491 (16) | 0.0462 (18) | −0.0085 (13) | −0.0038 (14) | −0.0060 (14) |
C8 | 0.0409 (16) | 0.0540 (17) | 0.0425 (17) | 0.0003 (13) | −0.0024 (14) | −0.0029 (14) |
C4 | 0.0501 (17) | 0.0372 (14) | 0.0562 (19) | −0.0027 (13) | −0.0070 (15) | −0.0045 (13) |
C2 | 0.062 (2) | 0.0568 (18) | 0.061 (2) | −0.0018 (16) | −0.0130 (18) | −0.0067 (17) |
C14 | 0.0578 (18) | 0.0698 (19) | 0.072 (2) | 0.0142 (16) | −0.0101 (17) | −0.0128 (18) |
N3 | 0.0551 (15) | 0.0529 (15) | 0.0674 (17) | −0.0011 (12) | −0.0007 (14) | −0.0246 (13) |
N4 | 0.0623 (17) | 0.0722 (17) | 0.0661 (18) | 0.0257 (14) | −0.0036 (14) | −0.0108 (15) |
C1 | 0.055 (2) | 0.071 (2) | 0.059 (2) | 0.0067 (16) | −0.0059 (19) | −0.0175 (16) |
C10 | 0.058 (2) | 0.0602 (18) | 0.084 (2) | 0.0060 (15) | 0.0020 (18) | −0.0284 (18) |
C9 | 0.0489 (17) | 0.0608 (17) | 0.092 (3) | 0.0092 (14) | −0.0112 (18) | −0.0334 (18) |
N2 | 0.086 (2) | 0.0751 (19) | 0.095 (2) | −0.0048 (16) | −0.0312 (18) | −0.0239 (18) |
C13 | 0.0640 (19) | 0.0525 (16) | 0.067 (2) | 0.0141 (15) | −0.0089 (17) | −0.0160 (16) |
N1 | 0.078 (2) | 0.124 (3) | 0.103 (3) | 0.0290 (19) | −0.036 (2) | −0.032 (2) |
C16 | 0.070 (2) | 0.109 (3) | 0.090 (3) | 0.034 (2) | −0.001 (2) | −0.014 (2) |
C15 | 0.096 (3) | 0.066 (2) | 0.125 (3) | 0.021 (2) | 0.001 (3) | −0.017 (2) |
C11—N3 | 1.457 (4) | C2—N2 | 1.141 (3) |
C11—H11A | 0.960 | C14—N4 | 1.462 (3) |
C11—H11B | 0.960 | C14—C13 | 1.505 (3) |
C11—H11C | 0.960 | C14—H14A | 0.970 |
C12—N3 | 1.452 (4) | C14—H14B | 0.970 |
C12—H12A | 0.960 | N3—C10 | 1.439 (3) |
C12—H12B | 0.960 | N4—C16 | 1.444 (4) |
C12—H12C | 0.960 | N4—C15 | 1.447 (4) |
S1—C6 | 1.752 (3) | C1—N1 | 1.138 (4) |
S1—C9 | 1.806 (3) | C10—C9 | 1.527 (4) |
S2—C5 | 1.742 (3) | C10—H10A | 0.970 |
S2—C13 | 1.818 (3) | C10—H10B | 0.970 |
C5—C4 | 1.390 (3) | C9—H9A | 0.970 |
C5—C6 | 1.425 (3) | C9—H9B | 0.970 |
C7—C6 | 1.372 (3) | C13—H13A | 0.970 |
C7—C8 | 1.388 (3) | C13—H13B | 0.970 |
C7—H7 | 0.930 | C16—H16A | 0.960 |
C3—C4 | 1.365 (3) | C16—H16B | 0.960 |
C3—C8 | 1.410 (3) | C16—H16C | 0.960 |
C3—C2 | 1.431 (4) | C15—H15A | 0.960 |
C8—C1 | 1.423 (4) | C15—H15B | 0.960 |
C4—H4 | 0.930 | C15—H15C | 0.960 |
N3—C11—H11A | 109.5 | H14A—C14—H14B | 108.0 |
N3—C11—H11B | 109.5 | C10—N3—C12 | 112.2 (3) |
H11A—C11—H11B | 109.5 | C10—N3—C11 | 111.2 (3) |
N3—C11—H11C | 109.5 | C12—N3—C11 | 110.0 (3) |
H11A—C11—H11C | 109.5 | C16—N4—C15 | 110.2 (3) |
H11B—C11—H11C | 109.5 | C16—N4—C14 | 110.2 (2) |
N3—C12—H12A | 109.5 | C15—N4—C14 | 111.0 (2) |
N3—C12—H12B | 109.5 | N1—C1—C8 | 178.9 (3) |
H12A—C12—H12B | 109.5 | N3—C10—C9 | 112.8 (2) |
N3—C12—H12C | 109.5 | N3—C10—H10A | 109.0 |
H12A—C12—H12C | 109.5 | C9—C10—H10A | 109.0 |
H12B—C12—H12C | 109.5 | N3—C10—H10B | 109.0 |
C6—S1—C9 | 103.37 (12) | C9—C10—H10B | 109.0 |
C5—S2—C13 | 103.21 (12) | H10A—C10—H10B | 107.8 |
C4—C5—C6 | 117.7 (2) | C10—C9—S1 | 107.2 (2) |
C4—C5—S2 | 124.6 (2) | C10—C9—H9A | 110.3 |
C6—C5—S2 | 117.66 (19) | S1—C9—H9A | 110.3 |
C6—C7—C8 | 121.6 (2) | C10—C9—H9B | 110.3 |
C6—C7—H7 | 119.2 | S1—C9—H9B | 110.3 |
C8—C7—H7 | 119.2 | H9A—C9—H9B | 108.5 |
C7—C6—C5 | 119.8 (2) | C14—C13—S2 | 107.3 (2) |
C7—C6—S1 | 124.77 (19) | C14—C13—H13A | 110.3 |
C5—C6—S1 | 115.40 (19) | S2—C13—H13A | 110.3 |
C4—C3—C8 | 119.9 (2) | C14—C13—H13B | 110.3 |
C4—C3—C2 | 120.2 (3) | S2—C13—H13B | 110.3 |
C8—C3—C2 | 120.0 (3) | H13A—C13—H13B | 108.5 |
C7—C8—C3 | 118.6 (2) | N4—C16—H16A | 109.5 |
C7—C8—C1 | 120.8 (2) | N4—C16—H16B | 109.5 |
C3—C8—C1 | 120.5 (2) | H16A—C16—H16B | 109.5 |
C3—C4—C5 | 122.2 (2) | N4—C16—H16C | 109.5 |
C3—C4—H4 | 118.9 | H16A—C16—H16C | 109.5 |
C5—C4—H4 | 118.9 | H16B—C16—H16C | 109.5 |
N2—C2—C3 | 179.4 (4) | N4—C15—H15A | 109.5 |
N4—C14—C13 | 111.1 (2) | N4—C15—H15B | 109.5 |
N4—C14—H14A | 109.4 | H15A—C15—H15B | 109.5 |
C13—C14—H14A | 109.4 | N4—C15—H15C | 109.5 |
N4—C14—H14B | 109.4 | H15A—C15—H15C | 109.5 |
C13—C14—H14B | 109.4 | H15B—C15—H15C | 109.5 |
C13—S2—C5—C4 | 5.3 (3) | C2—C3—C8—C1 | −2.4 (4) |
C13—S2—C5—C6 | −174.5 (2) | C8—C3—C4—C5 | −0.4 (4) |
C8—C7—C6—C5 | 2.1 (4) | C2—C3—C4—C5 | 179.6 (3) |
C8—C7—C6—S1 | −178.5 (2) | C6—C5—C4—C3 | 2.5 (4) |
C4—C5—C6—C7 | −3.3 (4) | S2—C5—C4—C3 | −177.3 (2) |
S2—C5—C6—C7 | 176.5 (2) | C13—C14—N4—C16 | 171.6 (3) |
C4—C5—C6—S1 | 177.24 (19) | C13—C14—N4—C15 | −66.0 (3) |
S2—C5—C6—S1 | −3.0 (3) | C12—N3—C10—C9 | 65.4 (3) |
C9—S1—C6—C7 | 7.6 (3) | C11—N3—C10—C9 | −171.0 (3) |
C9—S1—C6—C5 | −172.9 (2) | N3—C10—C9—S1 | 53.2 (3) |
C6—C7—C8—C1 | −178.5 (3) | C6—S1—C9—C10 | 165.6 (2) |
C4—C3—C8—C7 | −0.9 (4) | N4—C14—C13—S2 | −175.0 (2) |
C2—C3—C8—C7 | 179.1 (2) | C5—S2—C13—C14 | −179.3 (2) |
C4—C3—C8—C1 | 177.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···N1i | 0.96 | 2.83 | 3.768 (5) | 166 |
C12—H12C···N1ii | 0.96 | 2.86 | 3.731 (5) | 152 |
C7—H7···N3iii | 0.93 | 2.83 | 3.737 (3) | 165 |
C13—H13A···N2iv | 0.97 | 2.69 | 3.597 (4) | 155 |
C15—H15B···N2iv | 0.96 | 2.84 | 3.779 (5) | 166 |
C10—H10B···N1v | 0.97 | 2.90 | 3.789 (5) | 154 |
C13—H13B···N4vi | 0.97 | 2.89 | 3.738 (4) | 147 |
C16—H16B···N2vii | 0.96 | 2.99 | 3.899 (5) | 159 |
C11—H11C···Cg1viii | 0.96 | 2.90 | 3.738 (4) | 147 |
Symmetry codes: (i) x+1, −y+3/2, z+1/2; (ii) x+1/2, −y+3/2, −z+1; (iii) x−1/2, y, −z+3/2; (iv) −x, −y+1, −z+1; (v) x+1/2, y, −z+3/2; (vi) −x+1, −y+1, −z+1; (vii) −x+1/2, −y+1, z+1/2; (viii) x, −y+1/2, z+1/2. |