Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033027/hg6256sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033027/hg6256Isup2.hkl |
CCDC reference: 289770
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.006 Å
- R factor = 0.047
- wR factor = 0.105
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.676 0.999 Tmin(prime) and Tmax expected: 0.894 0.994 RR(prime) = 0.752 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.75 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 25.00 From the CIF: _reflns_number_total 1553 Count of symmetry unique reflns 929 Completeness (_total/calc) 167.17% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 624 Fraction of Friedel pairs measured 0.672 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 0 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.07; Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
C9H8N2O2S | F(000) = 216 |
Mr = 208.23 | Dx = 1.470 Mg m−3 |
Monoclinic, P21 | Melting point: 457 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3233 (8) Å | Cell parameters from 21914 reflections |
b = 4.9446 (5) Å | θ = 2.0–25.0° |
c = 10.2051 (10) Å | µ = 0.32 mm−1 |
β = 91.388 (5)° | T = 160 K |
V = 470.32 (8) Å3 | Needle, colourless |
Z = 2 | 0.35 × 0.10 × 0.02 mm |
Nonius KappaCCD area-detector diffractometer | 1553 independent reflections |
Radiation source: Nonius FR590 sealed tube generator | 1295 reflections with I > 2σ(I) |
Horizontally mounted graphite crystal monochromator | Rint = 0.083 |
Detector resolution: 9 pixels mm-1 | θmax = 25.0°, θmin = 2.2° |
φ and ω scans with κ offsets | h = −11→11 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −5→5 |
Tmin = 0.676, Tmax = 0.999 | l = −11→12 |
6143 measured reflections |
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)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.105 | w = 1/[σ2(Fo2) + (0.0334P)2 + 0.2737P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1553 reflections | Δρmax = 0.19 e Å−3 |
131 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Absolute structure: Flack & Bernardinelli (1999, 2000), 636 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (14) |
Experimental. Solvent used: DMF Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 1.772 (4) Frames collected: 401 Seconds exposure per frame: 70 Degrees rotation per frame: 1.0 Crystal-Detector distance (mm): 30.0 |
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 | ||
S2 | 0.17001 (10) | −0.3624 (2) | −0.21573 (10) | 0.0448 (3) | |
O1 | 0.1531 (2) | 0.0297 (6) | −0.0353 (2) | 0.0371 (7) | |
O7 | 0.3092 (2) | 0.5490 (5) | 0.1677 (2) | 0.0397 (7) | |
N3 | 0.3692 (3) | −0.0519 (7) | −0.0891 (3) | 0.0395 (8) | |
H3 | 0.441 (4) | −0.150 (10) | −0.115 (4) | 0.046 (12)* | |
N4 | 0.3776 (3) | 0.1482 (8) | 0.0055 (3) | 0.0392 (7) | |
C2 | 0.2361 (4) | −0.1301 (9) | −0.1157 (3) | 0.0348 (9) | |
C5 | 0.2476 (3) | 0.1896 (8) | 0.0327 (3) | 0.0336 (10) | |
C6 | 0.1914 (3) | 0.3818 (9) | 0.1319 (4) | 0.0349 (9) | |
H61 | 0.1117 | 0.4909 | 0.0938 | 0.042* | |
H62 | 0.1562 | 0.2828 | 0.2091 | 0.042* | |
C8 | 0.2887 (4) | 0.7254 (8) | 0.2709 (4) | 0.0378 (10) | |
C9 | 0.4070 (4) | 0.8827 (10) | 0.3045 (4) | 0.0435 (10) | |
H9 | 0.4941 | 0.8612 | 0.2591 | 0.052* | |
C10 | 0.3982 (5) | 1.0702 (9) | 0.4037 (4) | 0.0523 (13) | |
H10 | 0.4785 | 1.1808 | 0.4256 | 0.063* | |
C11 | 0.2715 (5) | 1.0974 (11) | 0.4717 (4) | 0.0582 (14) | |
H11 | 0.2653 | 1.2247 | 0.5411 | 0.070* | |
C12 | 0.1560 (5) | 0.9401 (10) | 0.4382 (4) | 0.0540 (12) | |
H12 | 0.0695 | 0.9602 | 0.4845 | 0.065* | |
C13 | 0.1623 (5) | 0.7498 (9) | 0.3369 (4) | 0.0446 (11) | |
H13 | 0.0816 | 0.6406 | 0.3144 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2 | 0.0417 (5) | 0.0478 (6) | 0.0447 (5) | −0.0021 (6) | −0.0044 (4) | −0.0076 (6) |
O1 | 0.0272 (12) | 0.0427 (17) | 0.0412 (14) | −0.0039 (11) | −0.0017 (11) | −0.0022 (12) |
O7 | 0.0331 (13) | 0.0442 (19) | 0.0417 (16) | −0.0039 (12) | 0.0006 (11) | −0.0070 (13) |
N3 | 0.0276 (16) | 0.043 (2) | 0.048 (2) | 0.0021 (15) | 0.0003 (14) | −0.0107 (17) |
N4 | 0.0331 (15) | 0.0422 (19) | 0.0421 (17) | −0.0023 (18) | −0.0052 (12) | −0.0078 (19) |
C2 | 0.0330 (19) | 0.035 (2) | 0.036 (2) | 0.0005 (18) | −0.0023 (16) | 0.0001 (17) |
C5 | 0.0279 (18) | 0.037 (3) | 0.0355 (19) | −0.0001 (17) | −0.0040 (15) | 0.0033 (18) |
C6 | 0.0284 (18) | 0.036 (2) | 0.040 (2) | −0.0032 (18) | 0.0005 (16) | 0.0024 (19) |
C8 | 0.043 (2) | 0.035 (3) | 0.035 (2) | 0.0077 (18) | −0.0032 (17) | 0.0015 (18) |
C9 | 0.047 (2) | 0.041 (3) | 0.043 (2) | −0.001 (2) | −0.0064 (18) | 0.004 (2) |
C10 | 0.062 (3) | 0.047 (3) | 0.047 (3) | 0.002 (2) | −0.016 (2) | 0.000 (2) |
C11 | 0.088 (3) | 0.050 (4) | 0.036 (2) | 0.013 (3) | −0.007 (2) | −0.006 (2) |
C12 | 0.072 (3) | 0.048 (3) | 0.043 (3) | 0.014 (2) | 0.009 (2) | 0.000 (2) |
C13 | 0.050 (3) | 0.040 (3) | 0.044 (2) | 0.003 (2) | 0.0024 (19) | 0.0051 (19) |
S2—C2 | 1.647 (4) | C8—C13 | 1.377 (5) |
O1—C5 | 1.362 (4) | C8—C9 | 1.386 (6) |
O1—C2 | 1.388 (5) | C9—C10 | 1.376 (6) |
O7—C8 | 1.384 (4) | C9—H9 | 0.9500 |
O7—C6 | 1.416 (4) | C10—C11 | 1.391 (6) |
N3—C2 | 1.321 (5) | C10—H10 | 0.9500 |
N3—N4 | 1.383 (5) | C11—C12 | 1.365 (7) |
N3—H3 | 0.87 (5) | C11—H11 | 0.9500 |
N4—C5 | 1.266 (4) | C12—C13 | 1.400 (6) |
C5—C6 | 1.492 (5) | C12—H12 | 0.9500 |
C6—H61 | 0.9900 | C13—H13 | 0.9500 |
C6—H62 | 0.9900 | ||
C5—O1—C2 | 105.6 (3) | C13—C8—O7 | 124.3 (4) |
C8—O7—C6 | 116.3 (3) | C13—C8—C9 | 121.0 (4) |
C2—N3—N4 | 112.9 (3) | O7—C8—C9 | 114.7 (3) |
C2—N3—H3 | 120 (3) | C10—C9—C8 | 119.9 (4) |
N4—N3—H3 | 125 (3) | C10—C9—H9 | 120.1 |
C5—N4—N3 | 103.3 (3) | C8—C9—H9 | 120.1 |
N3—C2—O1 | 104.3 (3) | C9—C10—C11 | 119.9 (4) |
N3—C2—S2 | 131.8 (3) | C9—C10—H10 | 120.0 |
O1—C2—S2 | 123.9 (3) | C11—C10—H10 | 120.0 |
N4—C5—O1 | 113.9 (4) | C12—C11—C10 | 119.6 (4) |
N4—C5—C6 | 127.3 (3) | C12—C11—H11 | 120.2 |
O1—C5—C6 | 118.8 (3) | C10—C11—H11 | 120.2 |
O7—C6—C5 | 105.3 (3) | C11—C12—C13 | 121.4 (4) |
O7—C6—H61 | 110.7 | C11—C12—H12 | 119.3 |
C5—C6—H61 | 110.7 | C13—C12—H12 | 119.3 |
O7—C6—H62 | 110.7 | C8—C13—C12 | 118.2 (4) |
C5—C6—H62 | 110.7 | C8—C13—H13 | 120.9 |
H61—C6—H62 | 108.8 | C12—C13—H13 | 120.9 |
C2—N3—N4—C5 | −1.0 (4) | O1—C5—C6—O7 | −169.9 (3) |
N4—N3—C2—O1 | 0.8 (4) | C6—O7—C8—C13 | −1.3 (5) |
N4—N3—C2—S2 | −178.2 (3) | C6—O7—C8—C9 | 179.1 (4) |
C5—O1—C2—N3 | −0.2 (4) | C13—C8—C9—C10 | −1.2 (6) |
C5—O1—C2—S2 | 178.8 (3) | O7—C8—C9—C10 | 178.5 (3) |
N3—N4—C5—O1 | 0.9 (4) | C8—C9—C10—C11 | 1.3 (6) |
N3—N4—C5—C6 | 178.4 (4) | C9—C10—C11—C12 | −0.9 (7) |
C2—O1—C5—N4 | −0.4 (5) | C10—C11—C12—C13 | 0.4 (7) |
C2—O1—C5—C6 | −178.2 (3) | O7—C8—C13—C12 | −179.0 (3) |
C8—O7—C6—C5 | −172.6 (3) | C9—C8—C13—C12 | 0.6 (6) |
N4—C5—C6—O7 | 12.6 (6) | C11—C12—C13—C8 | −0.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N4i | 0.87 (5) | 2.24 (4) | 2.899 (5) | 132 (3) |
C6—H61···O1ii | 0.99 | 2.53 | 3.416 (4) | 148 |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x, y+1/2, −z. |