Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016636/ob6520sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016636/ob6520Isup2.hkl |
CCDC reference: 274608
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.005 Å
- Disorder in solvent or counterion
- R factor = 0.061
- wR factor = 0.216
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.89
Author Response: A two-dmensional detector (IP) was used in combination with Cu as radiation. |
Alert level B REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 68.11 From the CIF: _diffrn_reflns_theta_full 68.11 From the CIF: _reflns_number_total 2164 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2427 Completeness (_total/calc) 89.16% PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.89
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 2 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C11 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C13 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 68.11 From the CIF: _reflns_number_total 2164 From the CIF: _diffrn_reflns_limit_ max hkl 8. 10. 10. From the CIF: _diffrn_reflns_limit_ min hkl -8. -10. -11. TEST1: Expected hkl limits for theta max Calculated maximum hkl 8. 10. 13. Calculated minimum hkl -8. -10. -13.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.
C20H10Cl2N2S2·2C4H9NO | Z = 1 |
Mr = 587.58 | F(000) = 306.00 |
Triclinic, P1 | Dx = 1.468 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.5418 Å |
a = 7.156 (2) Å | Cell parameters from 5253 reflections |
b = 8.941 (3) Å | θ = 4.1–68.0° |
c = 11.487 (4) Å | µ = 3.95 mm−1 |
α = 104.32 (2)° | T = 93 K |
β = 96.91 (2)° | Platelet, dark green |
γ = 107.369 (18)° | 0.40 × 0.40 × 0.08 mm |
V = 664.5 (4) Å3 |
Rigaku R-AXIS RAPID-F imaging-plate diffractometer | 1551 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.039 |
72 frames, Δ ω = 10° scans | θmax = 68.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −8→8 |
Tmin = 0.281, Tmax = 0.729 | k = −10→10 |
5955 measured reflections | l = −11→10 |
2164 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.1319P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.217 | (Δ/σ)max < 0.001 |
S = 1.18 | Δρmax = 0.46 e Å−3 |
2164 reflections | Δρmin = −0.53 e Å−3 |
171 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
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 | Occ. (<1) | |
Cl1 | −0.05006 (15) | 0.06167 (11) | −0.16885 (10) | 0.0425 (4) | |
S1 | 0.11519 (16) | 0.63783 (12) | −0.28496 (10) | 0.0454 (4) | |
O1 | 0.6372 (4) | 0.8346 (4) | 0.3447 (3) | 0.0475 (8) | |
N1 | 0.4336 (4) | 0.7451 (4) | 0.1031 (3) | 0.0299 (8) | |
H1N | 0.4894 | 0.7667 | 0.1807 | 0.036* | |
C1 | 0.1058 (5) | 0.3828 (4) | −0.1471 (4) | 0.0336 (10) | |
H1 | 0.0390 | 0.3525 | −0.2305 | 0.040* | |
C2 | 0.0910 (5) | 0.2668 (4) | −0.0882 (4) | 0.0331 (9) | |
C3 | 0.1858 (6) | 0.3040 (5) | 0.0335 (4) | 0.0376 (10) | |
H3 | 0.1731 | 0.2199 | 0.0720 | 0.045* | |
C4 | 0.2984 (5) | 0.4645 (4) | 0.0974 (4) | 0.0328 (9) | |
H4 | 0.3628 | 0.4919 | 0.1809 | 0.039* | |
C5 | 0.3185 (5) | 0.5890 (4) | 0.0389 (4) | 0.0303 (9) | |
C6 | 0.2213 (5) | 0.5492 (4) | −0.0838 (4) | 0.0302 (9) | |
C7 | 0.2383 (5) | 0.6751 (4) | −0.1460 (4) | 0.0336 (10) | |
C8 | 0.3711 (5) | 0.8413 (4) | −0.0718 (4) | 0.0297 (9) | |
C9 | 0.4662 (5) | 0.8708 (5) | 0.0513 (4) | 0.0305 (9) | |
C10 | 0.4063 (5) | 0.9725 (4) | −0.1203 (4) | 0.0320 (9) | |
H10 | 0.3420 | 0.9549 | −0.2023 | 0.038* | |
C11 | 0.8909 (6) | 0.7842 (6) | 0.4931 (5) | 0.0612 (14) | |
H11A | 0.9666 | 0.7607 | 0.5591 | 0.092* | 0.623 (13) |
H11B | 0.9578 | 0.8971 | 0.4930 | 0.092* | 0.623 (13) |
H11C | 0.8842 | 0.7078 | 0.4139 | 0.092* | 0.623 (13) |
H11D | 0.8766 | 0.7589 | 0.5706 | 0.092* | 0.377 (13) |
H11E | 1.0036 | 0.8864 | 0.5089 | 0.092* | 0.377 (13) |
H11F | 0.9158 | 0.6944 | 0.4360 | 0.092* | 0.377 (13) |
C12 | 0.6031 (6) | 0.7082 (5) | 0.6163 (4) | 0.0446 (11) | |
H12A | 0.7111 | 0.6936 | 0.6685 | 0.067* | 0.623 (13) |
H12B | 0.4920 | 0.6035 | 0.5826 | 0.067* | 0.623 (13) |
H12C | 0.5562 | 0.7905 | 0.6653 | 0.067* | 0.623 (13) |
H12D | 0.4832 | 0.6798 | 0.6509 | 0.067* | 0.377 (13) |
H12E | 0.7107 | 0.7990 | 0.6776 | 0.067* | 0.377 (13) |
H12F | 0.6461 | 0.6125 | 0.5937 | 0.067* | 0.377 (13) |
C13 | 0.3557 (6) | 0.7754 (6) | 0.4540 (5) | 0.0582 (14) | |
H13A | 0.3423 | 0.7413 | 0.5282 | 0.087* | 0.623 (13) |
H13B | 0.2556 | 0.6927 | 0.3837 | 0.087* | 0.623 (13) |
H13C | 0.3349 | 0.8812 | 0.4655 | 0.087* | 0.623 (13) |
H13D | 0.2581 | 0.7417 | 0.5037 | 0.087* | 0.377 (13) |
H13E | 0.3046 | 0.7053 | 0.3686 | 0.087* | 0.377 (13) |
H13F | 0.3777 | 0.8900 | 0.4571 | 0.087* | 0.377 (13) |
N2 | 0.6791 (10) | 0.7641 (6) | 0.5140 (6) | 0.0385 (19)* | 0.623 (13) |
C14 | 0.5668 (11) | 0.7929 (8) | 0.4295 (7) | 0.041 (2)* | 0.623 (13) |
N3 | 0.5569 (15) | 0.7585 (10) | 0.5055 (9) | 0.031 (3)* | 0.377 (13) |
C15 | 0.6937 (17) | 0.8049 (12) | 0.4354 (11) | 0.032 (3)* | 0.377 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0476 (7) | 0.0311 (5) | 0.0499 (9) | 0.0117 (4) | 0.0148 (5) | 0.0141 (5) |
S1 | 0.0514 (7) | 0.0400 (6) | 0.0436 (9) | 0.0125 (5) | 0.0086 (5) | 0.0149 (5) |
O1 | 0.0568 (19) | 0.0545 (19) | 0.032 (2) | 0.0167 (15) | 0.0078 (15) | 0.0185 (15) |
N1 | 0.0371 (17) | 0.0338 (16) | 0.024 (2) | 0.0159 (13) | 0.0071 (13) | 0.0123 (14) |
C1 | 0.032 (2) | 0.036 (2) | 0.038 (3) | 0.0159 (16) | 0.0148 (18) | 0.0113 (18) |
C2 | 0.039 (2) | 0.034 (2) | 0.031 (3) | 0.0160 (17) | 0.0126 (18) | 0.0104 (17) |
C3 | 0.040 (2) | 0.035 (2) | 0.051 (3) | 0.0189 (17) | 0.023 (2) | 0.021 (2) |
C4 | 0.038 (2) | 0.035 (2) | 0.034 (3) | 0.0163 (17) | 0.0159 (18) | 0.0180 (18) |
C5 | 0.032 (2) | 0.037 (2) | 0.033 (3) | 0.0185 (16) | 0.0154 (17) | 0.0163 (18) |
C6 | 0.0292 (19) | 0.0322 (19) | 0.034 (3) | 0.0137 (15) | 0.0119 (17) | 0.0124 (17) |
C7 | 0.031 (2) | 0.033 (2) | 0.041 (3) | 0.0150 (16) | 0.0112 (18) | 0.0131 (18) |
C8 | 0.032 (2) | 0.0324 (19) | 0.030 (3) | 0.0137 (15) | 0.0111 (16) | 0.0120 (17) |
C9 | 0.032 (2) | 0.037 (2) | 0.032 (3) | 0.0195 (16) | 0.0114 (17) | 0.0132 (17) |
C10 | 0.037 (2) | 0.037 (2) | 0.031 (3) | 0.0197 (17) | 0.0105 (18) | 0.0143 (18) |
C11 | 0.040 (3) | 0.069 (3) | 0.063 (4) | 0.023 (2) | 0.006 (2) | −0.003 (3) |
C12 | 0.045 (2) | 0.047 (2) | 0.045 (3) | 0.0164 (19) | 0.011 (2) | 0.017 (2) |
C13 | 0.033 (2) | 0.058 (3) | 0.073 (4) | 0.017 (2) | 0.005 (2) | 0.004 (3) |
Cl1—C2 | 1.752 (4) | C11—H11A | 0.9800 |
S1—C7 | 1.630 (4) | C11—H11B | 0.9800 |
O1—C15 | 1.191 (11) | C11—H11C | 0.9800 |
O1—C14 | 1.236 (8) | C11—H11D | 0.9800 |
N1—C5 | 1.352 (5) | C11—H11E | 0.9800 |
N1—C9 | 1.370 (4) | C11—H11F | 0.9800 |
N1—H1N | 0.8800 | C12—N3 | 1.485 (10) |
C1—C2 | 1.358 (5) | C12—N2 | 1.487 (7) |
C1—C6 | 1.418 (5) | C12—H12A | 0.9800 |
C1—H1 | 0.9500 | C12—H12B | 0.9800 |
C2—C3 | 1.390 (6) | C12—H12C | 0.9800 |
C3—C4 | 1.376 (5) | C12—H12D | 0.9800 |
C3—H3 | 0.9500 | C12—H12E | 0.9800 |
C4—C5 | 1.417 (5) | C12—H12F | 0.9800 |
C4—H4 | 0.9500 | C13—C14 | 1.539 (8) |
C5—C6 | 1.402 (6) | C13—N3 | 1.554 (10) |
C6—C7 | 1.459 (5) | C13—H13A | 0.9800 |
C7—C8 | 1.475 (5) | C13—H13B | 0.9800 |
C8—C10 | 1.389 (5) | C13—H13C | 0.9800 |
C8—C9 | 1.417 (6) | C13—H13D | 0.9800 |
C9—C10i | 1.392 (5) | C13—H13E | 0.9800 |
C10—H10 | 0.9500 | C13—H13F | 0.9800 |
C11—N2 | 1.527 (7) | N2—C14 | 1.309 (12) |
C11—C15 | 1.568 (12) | N3—C15 | 1.376 (18) |
C5—N1—C9 | 122.2 (3) | H11D—C11—H11E | 109.5 |
C5—N1—H1N | 118.9 | C15—C11—H11F | 109.5 |
C9—N1—H1N | 118.9 | H11D—C11—H11F | 109.5 |
C2—C1—C6 | 119.8 (4) | H11E—C11—H11F | 109.5 |
C2—C1—H1 | 120.1 | N2—C12—H12A | 109.5 |
C6—C1—H1 | 120.1 | N2—C12—H12B | 109.5 |
C1—C2—C3 | 122.5 (4) | H12A—C12—H12B | 109.5 |
C1—C2—Cl1 | 118.9 (3) | N2—C12—H12C | 109.5 |
C3—C2—Cl1 | 118.5 (3) | H12A—C12—H12C | 109.5 |
C4—C3—C2 | 119.0 (4) | H12B—C12—H12C | 109.5 |
C4—C3—H3 | 120.5 | N3—C12—H12D | 109.5 |
C2—C3—H3 | 120.5 | N3—C12—H12E | 109.5 |
C3—C4—C5 | 120.2 (4) | H12D—C12—H12E | 109.5 |
C3—C4—H4 | 119.9 | N3—C12—H12F | 109.5 |
C5—C4—H4 | 119.9 | H12D—C12—H12F | 109.5 |
N1—C5—C6 | 121.1 (3) | H12E—C12—H12F | 109.5 |
N1—C5—C4 | 118.9 (4) | C14—C13—H13A | 109.5 |
C6—C5—C4 | 120.0 (4) | C14—C13—H13B | 109.5 |
C5—C6—C1 | 118.5 (4) | H13A—C13—H13B | 109.5 |
C5—C6—C7 | 121.2 (3) | C14—C13—H13C | 109.5 |
C1—C6—C7 | 120.3 (4) | H13A—C13—H13C | 109.5 |
C6—C7—C8 | 114.8 (4) | H13B—C13—H13C | 109.5 |
C6—C7—S1 | 123.1 (3) | N3—C13—H13D | 109.5 |
C8—C7—S1 | 122.1 (3) | N3—C13—H13E | 109.5 |
C10—C8—C9 | 118.4 (4) | H13D—C13—H13E | 109.5 |
C10—C8—C7 | 121.1 (4) | N3—C13—H13F | 109.5 |
C9—C8—C7 | 120.5 (3) | H13D—C13—H13F | 109.5 |
N1—C9—C10i | 119.6 (4) | H13E—C13—H13F | 109.5 |
N1—C9—C8 | 120.2 (4) | C14—N2—C12 | 122.8 (7) |
C10i—C9—C8 | 120.2 (3) | C14—N2—C11 | 113.6 (6) |
C8—C10—C9i | 121.4 (4) | C12—N2—C11 | 123.5 (5) |
C8—C10—H10 | 119.3 | O1—C14—N2 | 119.8 (7) |
C9i—C10—H10 | 119.3 | O1—C14—C13 | 127.5 (7) |
N2—C11—H11A | 109.5 | N2—C14—C13 | 112.6 (7) |
N2—C11—H11B | 109.5 | C15—N3—C12 | 123.8 (9) |
H11A—C11—H11B | 109.5 | C15—N3—C13 | 109.5 (8) |
N2—C11—H11C | 109.5 | C12—N3—C13 | 126.6 (7) |
H11A—C11—H11C | 109.5 | O1—C15—N3 | 118.0 (10) |
H11B—C11—H11C | 109.5 | O1—C15—C11 | 135.3 (10) |
C15—C11—H11D | 109.5 | N3—C15—C11 | 106.2 (9) |
C15—C11—H11E | 109.5 |
Symmetry code: (i) −x+1, −y+2, −z. |
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