Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806001498/is6179sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806001498/is6179Isup2.hkl |
CCDC reference: 298476
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.110
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.94 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.33 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for S1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C16H14N2O4S | F(000) = 688.00 |
Mr = 330.36 | Dx = 1.439 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2yn | Cell parameters from 11903 reflections |
a = 10.261 (5) Å | θ = 3.1–27.5° |
b = 8.573 (4) Å | µ = 0.23 mm−1 |
c = 17.898 (7) Å | T = 298 K |
β = 104.415 (16)° | Prism, brown |
V = 1524.9 (11) Å3 | 0.55 × 0.45 × 0.32 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 2423 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.026 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −13→13 |
Tmin = 0.859, Tmax = 0.928 | k = −11→8 |
14375 measured reflections | l = −23→23 |
3489 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.041 | w = 1/[0.0009Fo2 + σ(Fo2)]/(4Fo2) |
wR(F2) = 0.110 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.29 e Å−3 |
3489 reflections | Δρmin = −0.29 e Å−3 |
208 parameters |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.08023 (4) | 0.19162 (6) | 0.42985 (3) | 0.04754 (13) | |
O1 | 0.35568 (12) | 0.11824 (18) | 0.48645 (8) | 0.0703 (4) | |
O2 | 0.30342 (12) | 0.64992 (17) | 0.32673 (8) | 0.0627 (4) | |
O3 | 0.09843 (18) | 0.1957 (2) | 0.51137 (8) | 0.0879 (5) | |
O4 | −0.03938 (12) | 0.25699 (18) | 0.38319 (10) | 0.0757 (4) | |
N1 | 0.34184 (12) | 0.24132 (17) | 0.44507 (8) | 0.0416 (3) | |
N2 | 0.31393 (12) | 0.51750 (16) | 0.36088 (6) | 0.0400 (3) | |
C1 | 0.21908 (14) | 0.29783 (19) | 0.40913 (9) | 0.0371 (4) | |
C2 | 0.45582 (14) | 0.31950 (19) | 0.43611 (9) | 0.0385 (4) | |
C3 | 0.58354 (16) | 0.2576 (2) | 0.46994 (10) | 0.0501 (5) | |
C4 | 0.69373 (17) | 0.3366 (2) | 0.46096 (11) | 0.0558 (5) | |
C5 | 0.68065 (17) | 0.4767 (2) | 0.42123 (11) | 0.0590 (5) | |
C6 | 0.55744 (17) | 0.5396 (2) | 0.38884 (10) | 0.0522 (5) | |
C7 | 0.44206 (14) | 0.4588 (2) | 0.39541 (9) | 0.0387 (4) | |
C8 | 0.20351 (13) | 0.43429 (19) | 0.36421 (9) | 0.0353 (3) | |
C9 | 0.07384 (14) | 0.4953 (2) | 0.31598 (9) | 0.0388 (4) | |
C10 | −0.00435 (17) | 0.5978 (2) | 0.34510 (11) | 0.0490 (5) | |
C11 | −0.12180 (19) | 0.6559 (2) | 0.29735 (13) | 0.0658 (6) | |
C12 | −0.1596 (2) | 0.6093 (3) | 0.22128 (14) | 0.0768 (7) | |
C13 | −0.0827 (2) | 0.5067 (3) | 0.19256 (12) | 0.0759 (7) | |
C14 | 0.0355 (2) | 0.4495 (2) | 0.23933 (10) | 0.0574 (5) | |
C15 | 0.0957 (2) | −0.0008 (2) | 0.39816 (11) | 0.0547 (5) | |
C16 | 0.0978 (3) | −0.0065 (3) | 0.31464 (14) | 0.1039 (10) | |
H3 | 0.5927 | 0.1648 | 0.4977 | 0.059* | |
H4 | 0.7790 | 0.2959 | 0.4819 | 0.066* | |
H5 | 0.7575 | 0.5290 | 0.4163 | 0.072* | |
H6 | 0.5499 | 0.6346 | 0.3631 | 0.063* | |
H10 | 0.0215 | 0.6278 | 0.3966 | 0.059* | |
H11 | −0.1746 | 0.7261 | 0.3164 | 0.080* | |
H12 | −0.2383 | 0.6484 | 0.1892 | 0.088* | |
H13 | −0.1104 | 0.4746 | 0.1414 | 0.086* | |
H14 | 0.0889 | 0.3811 | 0.2197 | 0.067* | |
H152 | 0.1780 | −0.0466 | 0.4291 | 0.067* | |
H151 | 0.0207 | −0.0627 | 0.4056 | 0.066* | |
H161 | 0.1694 | 0.0584 | 0.3067 | 0.134* | |
H162 | 0.0135 | 0.0309 | 0.2836 | 0.135* | |
H163 | 0.1119 | −0.1119 | 0.3003 | 0.134* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0412 (2) | 0.0462 (2) | 0.0612 (2) | −0.01251 (19) | 0.02392 (19) | −0.0006 (2) |
O1 | 0.0555 (8) | 0.0600 (9) | 0.0869 (9) | −0.0054 (6) | 0.0017 (7) | 0.0378 (7) |
O2 | 0.0558 (7) | 0.0502 (8) | 0.0829 (9) | −0.0055 (6) | 0.0187 (6) | 0.0231 (6) |
O3 | 0.1120 (13) | 0.0997 (13) | 0.0681 (9) | −0.0516 (10) | 0.0529 (9) | −0.0179 (8) |
O4 | 0.0338 (6) | 0.0595 (9) | 0.1352 (13) | −0.0053 (6) | 0.0238 (7) | 0.0170 (8) |
N1 | 0.0345 (6) | 0.0400 (7) | 0.0487 (7) | −0.0040 (5) | 0.0072 (5) | 0.0088 (6) |
N2 | 0.0353 (6) | 0.0372 (7) | 0.0487 (7) | −0.0038 (5) | 0.0128 (5) | 0.0068 (5) |
C1 | 0.0298 (7) | 0.0382 (8) | 0.0445 (8) | −0.0052 (6) | 0.0118 (6) | 0.0015 (6) |
C2 | 0.0311 (7) | 0.0421 (9) | 0.0427 (8) | −0.0011 (6) | 0.0098 (6) | −0.0016 (7) |
C3 | 0.0358 (8) | 0.0528 (11) | 0.0582 (10) | 0.0064 (7) | 0.0053 (7) | 0.0014 (8) |
C4 | 0.0304 (8) | 0.0747 (14) | 0.0609 (10) | 0.0047 (8) | 0.0088 (7) | −0.0066 (10) |
C5 | 0.0311 (8) | 0.0871 (15) | 0.0613 (10) | −0.0152 (9) | 0.0163 (7) | −0.0065 (10) |
C6 | 0.0404 (9) | 0.0621 (12) | 0.0563 (9) | −0.0135 (8) | 0.0164 (7) | 0.0068 (8) |
C7 | 0.0301 (7) | 0.0464 (9) | 0.0407 (8) | −0.0045 (6) | 0.0109 (6) | −0.0001 (7) |
C8 | 0.0296 (7) | 0.0365 (8) | 0.0408 (7) | −0.0014 (6) | 0.0105 (6) | −0.0020 (6) |
C9 | 0.0307 (7) | 0.0371 (8) | 0.0474 (8) | −0.0016 (6) | 0.0075 (6) | 0.0026 (6) |
C10 | 0.0419 (9) | 0.0446 (10) | 0.0614 (10) | 0.0032 (7) | 0.0143 (7) | 0.0028 (8) |
C11 | 0.0434 (10) | 0.0554 (13) | 0.1007 (17) | 0.0132 (9) | 0.0218 (10) | 0.0183 (11) |
C12 | 0.0425 (10) | 0.0860 (17) | 0.0898 (16) | 0.0092 (11) | −0.0068 (10) | 0.0337 (13) |
C13 | 0.0655 (14) | 0.0947 (18) | 0.0548 (11) | 0.0033 (13) | −0.0089 (10) | 0.0084 (11) |
C14 | 0.0522 (10) | 0.0668 (13) | 0.0498 (10) | 0.0064 (9) | 0.0063 (8) | −0.0037 (9) |
C15 | 0.0557 (10) | 0.0408 (10) | 0.0688 (11) | −0.0117 (8) | 0.0178 (8) | 0.0059 (8) |
C16 | 0.171 (3) | 0.0669 (17) | 0.0979 (17) | −0.0329 (18) | 0.0795 (19) | −0.0203 (14) |
S1—O3 | 1.4245 (15) | C10—C11 | 1.385 (2) |
S1—O4 | 1.4169 (13) | C11—C12 | 1.379 (3) |
S1—C1 | 1.8054 (17) | C12—C13 | 1.364 (3) |
S1—C15 | 1.764 (2) | C13—C14 | 1.381 (2) |
O1—N1 | 1.277 (2) | C15—C16 | 1.501 (3) |
O2—N2 | 1.2811 (19) | C3—H3 | 0.930 |
N1—C1 | 1.3534 (19) | C4—H4 | 0.930 |
N1—C2 | 1.391 (2) | C5—H5 | 0.930 |
N2—C7 | 1.3997 (19) | C6—H6 | 0.930 |
N2—C8 | 1.353 (2) | C10—H10 | 0.930 |
C1—C8 | 1.406 (2) | C11—H11 | 0.930 |
C2—C3 | 1.404 (2) | C12—H12 | 0.930 |
C2—C7 | 1.388 (2) | C13—H13 | 0.930 |
C3—C4 | 1.361 (2) | C14—H14 | 0.930 |
C4—C5 | 1.385 (3) | C15—H152 | 0.970 |
C5—C6 | 1.364 (2) | C15—H151 | 0.970 |
C6—C7 | 1.401 (2) | C16—H161 | 0.960 |
C8—C9 | 1.4890 (19) | C16—H162 | 0.960 |
C9—C10 | 1.377 (2) | C16—H163 | 0.960 |
C9—C14 | 1.387 (2) | ||
O1···O1i | 3.5217 (19) | C16···O2xii | 3.598 (3) |
O1···C3i | 3.337 (2) | C16···O2xi | 3.241 (3) |
O2···C14ii | 3.421 (2) | C16···N2xi | 3.485 (3) |
O2···C16iii | 3.598 (3) | S1···H4vi | 3.557 |
O2···C16ii | 3.241 (3) | S1···H151v | 3.534 |
O3···C10iv | 3.450 (2) | O1···H3i | 2.485 |
O3···C15v | 3.314 (2) | O1···H13xiii | 2.822 |
O4···C4vi | 3.435 (2) | O2···H14ii | 2.509 |
O4···C12vii | 3.430 (2) | O2···H161ii | 2.594 |
N1···C5viii | 3.449 (2) | O2···H162ii | 3.212 |
N1···C6viii | 3.450 (2) | O2···H163iii | 2.791 |
N2···C3viii | 3.522 (2) | O3···H5viii | 2.912 |
N2···C4viii | 3.444 (2) | O3···H10iv | 2.743 |
N2···C16ii | 3.485 (3) | O3···H11iv | 3.059 |
C1···C5viii | 3.530 (2) | O3···H151v | 2.431 |
C2···C6viii | 3.392 (2) | O4···H4vi | 2.889 |
C2···C7viii | 3.497 (2) | O4···H12vii | 2.505 |
C3···O1i | 3.337 (2) | N2···H161ii | 3.066 |
C3···N2viii | 3.522 (2) | C3···H13xi | 3.195 |
C3···C7viii | 3.479 (2) | C3···H152i | 3.213 |
C4···O4ix | 3.435 (2) | C4···H12xi | 3.262 |
C4···N2viii | 3.444 (2) | C4···H152i | 3.240 |
C5···N1viii | 3.449 (2) | C6···H162ii | 2.990 |
C5···C1viii | 3.530 (2) | C10···H5vi | 3.081 |
C6···N1viii | 3.450 (2) | C10···H151iii | 3.094 |
C6···C2viii | 3.392 (2) | C10···H163iii | 2.957 |
C7···C2viii | 3.497 (2) | C11···H5vi | 2.926 |
C7···C3viii | 3.479 (2) | C11···H151iii | 3.210 |
C10···O3iv | 3.450 (2) | C11···H163iii | 3.108 |
C12···O4x | 3.430 (2) | C14···H6xi | 3.258 |
C14···O2xi | 3.421 (2) | C15···H10xii | 3.272 |
C15···O3v | 3.314 (2) | ||
O3—S1—O4 | 117.87 (11) | C11—C12—C13 | 120.81 (19) |
O3—S1—C1 | 106.80 (9) | C12—C13—C14 | 120.22 (19) |
O3—S1—C15 | 110.66 (10) | C9—C14—C13 | 119.31 (19) |
O4—S1—C1 | 106.95 (8) | S1—C15—C16 | 112.05 (16) |
O4—S1—C15 | 108.31 (9) | C2—C3—H3 | 120.9 |
C1—S1—C15 | 105.48 (9) | C4—C3—H3 | 120.8 |
O1—N1—C1 | 121.84 (14) | C3—C4—H4 | 119.5 |
O1—N1—C2 | 119.32 (12) | C5—C4—H4 | 119.6 |
C1—N1—C2 | 118.84 (14) | C4—C5—H5 | 119.4 |
O2—N2—C7 | 119.17 (13) | C6—C5—H5 | 119.1 |
O2—N2—C8 | 121.09 (12) | C5—C6—H6 | 120.7 |
C7—N2—C8 | 119.73 (13) | C7—C6—H6 | 120.5 |
S1—C1—N1 | 114.24 (12) | C9—C10—H10 | 120.2 |
S1—C1—C8 | 123.64 (11) | C11—C10—H10 | 120.1 |
N1—C1—C8 | 121.97 (14) | C10—C11—H11 | 120.2 |
N1—C2—C3 | 119.30 (15) | C12—C11—H11 | 120.3 |
N1—C2—C7 | 119.77 (13) | C11—C12—H12 | 119.6 |
C3—C2—C7 | 120.92 (15) | C13—C12—H12 | 119.6 |
C2—C3—C4 | 118.34 (17) | C12—C13—H13 | 119.9 |
C3—C4—C5 | 120.98 (16) | C14—C13—H13 | 119.9 |
C4—C5—C6 | 121.46 (18) | C9—C14—H14 | 120.3 |
C5—C6—C7 | 118.83 (18) | C13—C14—H14 | 120.4 |
N2—C7—C2 | 120.19 (14) | S1—C15—H152 | 109.3 |
N2—C7—C6 | 120.37 (15) | S1—C15—H151 | 109.3 |
C2—C7—C6 | 119.44 (14) | C16—C15—H152 | 109.1 |
N2—C8—C1 | 119.13 (12) | C16—C15—H151 | 109.1 |
N2—C8—C9 | 115.25 (13) | H152—C15—H151 | 107.9 |
C1—C8—C9 | 125.57 (13) | C15—C16—H161 | 109.3 |
C8—C9—C10 | 121.70 (14) | C15—C16—H162 | 109.4 |
C8—C9—C14 | 117.84 (15) | C15—C16—H163 | 109.8 |
C10—C9—C14 | 120.43 (15) | H161—C16—H162 | 109.5 |
C9—C10—C11 | 119.70 (17) | H161—C16—H163 | 109.5 |
C10—C11—C12 | 119.5 (2) | H162—C16—H163 | 109.5 |
O3—S1—C1—N1 | 57.74 (15) | S1—C1—C8—C9 | −11.7 (2) |
O3—S1—C1—C8 | −117.86 (15) | N1—C1—C8—N2 | −4.5 (2) |
O3—S1—C15—C16 | −171.41 (18) | N1—C1—C8—C9 | 172.99 (15) |
O4—S1—C1—N1 | −175.21 (13) | N1—C2—C3—C4 | −179.50 (16) |
O4—S1—C1—C8 | 9.19 (17) | N1—C2—C7—N2 | −2.5 (2) |
O4—S1—C15—C16 | 58.0 (2) | N1—C2—C7—C6 | 177.86 (15) |
C1—S1—C15—C16 | −56.25 (19) | C3—C2—C7—N2 | 178.87 (15) |
C15—S1—C1—N1 | −60.04 (14) | C3—C2—C7—C6 | −0.8 (2) |
C15—S1—C1—C8 | 124.36 (14) | C7—C2—C3—C4 | −0.9 (2) |
O1—N1—C1—S1 | 3.6 (2) | C2—C3—C4—C5 | 1.7 (2) |
O1—N1—C1—C8 | 179.29 (15) | C3—C4—C5—C6 | −0.9 (3) |
O1—N1—C2—C3 | 2.8 (2) | C4—C5—C6—C7 | −0.8 (3) |
O1—N1—C2—C7 | −175.84 (15) | C5—C6—C7—N2 | −178.06 (16) |
C1—N1—C2—C3 | −176.83 (15) | C5—C6—C7—C2 | 1.6 (2) |
C1—N1—C2—C7 | 4.5 (2) | N2—C8—C9—C10 | −92.2 (2) |
C2—N1—C1—S1 | −176.77 (12) | N2—C8—C9—C14 | 85.8 (2) |
C2—N1—C1—C8 | −1.1 (2) | C1—C8—C9—C10 | 90.2 (2) |
O2—N2—C7—C2 | 176.69 (15) | C1—C8—C9—C14 | −91.8 (2) |
O2—N2—C7—C6 | −3.7 (2) | C8—C9—C10—C11 | 177.66 (17) |
O2—N2—C8—C1 | −173.30 (15) | C8—C9—C14—C13 | −178.55 (19) |
O2—N2—C8—C9 | 9.0 (2) | C10—C9—C14—C13 | −0.5 (3) |
C7—N2—C8—C1 | 6.5 (2) | C14—C9—C10—C11 | −0.3 (2) |
C7—N2—C8—C9 | −171.25 (14) | C9—C10—C11—C12 | 0.5 (3) |
C8—N2—C7—C2 | −3.1 (2) | C10—C11—C12—C13 | 0.1 (2) |
C8—N2—C7—C6 | 176.52 (15) | C11—C12—C13—C14 | −0.9 (4) |
S1—C1—C8—N2 | 170.77 (12) | C12—C13—C14—C9 | 1.1 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1/2, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) −x, −y+1, −z+1; (v) −x, −y, −z+1; (vi) x−1, y, z; (vii) −x−1/2, y−1/2, −z+1/2; (viii) −x+1, −y+1, −z+1; (ix) x+1, y, z; (x) −x−1/2, y+1/2, −z+1/2; (xi) −x+1/2, y−1/2, −z+1/2; (xii) x, y−1, z; (xiii) x+1/2, −y+1/2, z+1/2. |
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