Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030881/hg2077sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030881/hg2077IIsup2.hkl |
CCDC reference: 621343
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.087
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C3 ... 1.53 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O3 .. 3.22 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: X-SEED (Barbour, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED and POV-RAY (Persistence of Vision, 2004); software used to prepare material for publication: WinGX (Farrugia, 1999).
C17H15BrN4O3S | F(000) = 1760 |
Mr = 435.3 | Dx = 1.631 Mg m−3 |
Monoclinic, C2/c | Melting point: 428 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 23.4478 (3) Å | Cell parameters from 21515 reflections |
b = 10.0971 (2) Å | θ = 0.4–29.6° |
c = 15.2847 (2) Å | µ = 2.46 mm−1 |
β = 101.518 (1)° | T = 123 K |
V = 3545.85 (10) Å3 | Block, colourless |
Z = 8 | 0.25 × 0.25 × 0.1 mm |
Nonius KappaCCD diffractometer | 3411 reflections with I > 2σ(I) |
1° frames in φ and ω scans | Rint = 0.042 |
Absorption correction: empirical (using intensity measurements) (SORTAV; Otwinowski & Minor, 1997) | θmax = 27.5°, θmin = 1.8° |
Tmin = 0.578, Tmax = 0.791 | h = −30→30 |
18424 measured reflections | k = −13→13 |
4071 independent reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.044P)2 + 4.5742P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.087 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 1.15 e Å−3 |
4071 reflections | Δρmin = −0.60 e Å−3 |
237 parameters |
Experimental. 1H NMR(CDCl3, 400?MHz, δ, p.p.m.) 7.70(2H, d, J=8.8?Hz, ArH), 7.60(2H, d, J=8.8?Hz, ArH), 7.27–7.36(5H, m, ArH), 3.24(3H, s, CH3—N), 3.23(3H, s, CH3—N). 13 C NMR(CDCl3, 50?MHz, δ, p.p.m.) 184.3, 158.8, 157.3, 132.4, 132.2, 131.8, 131.0, 130.9, 130.3, 129.6, 129.2, 37.7, 37.5. m/z (APCI,+ve, MeOH: CH3CN:H2O 2:1:1) 435, 437 (M+1). Analysis, calculated for C17H15BrN4O3S: C 46.91, H 3.47, N 12.87, S 7.37%. found: C 47.17, H 3.53, N 12.89, S 7.08%. m.p. 427–429?K. |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 11.5572 (0.0185) x + 8.6350 (0.0052) y + 0.8964 (0.0136) z = 3.2977 (0.0026) * -0.0262 (0.0010) N2 * 0.0351 (0.0014) C2 * -0.0130 (0.0013) N3 * -0.0149 (0.0014) C1 * 0.0190 (0.0010) N1 - 0.3079 (0.0022) S1 Rms deviation of fitted atoms = 0.0231 14.8751 (0.0195) x + 6.8790 (0.0100) y + 3.5339 (0.0194) z = 4.0750 (0.0041) Angle to previous plane (with approximate e.s.d.) = 17.47 (0.14) * 0.0000 (0.0000) N2 * 0.0000 (0.0000) S1 * 0.0000 (0.0000) N1 Rms deviation of fitted atoms = 0.0000 11.2163 (0.0176) x + 8.4520 (0.0050) y + 2.5164 (0.0118) z = 3.2865 (0.0028) Angle to previous plane (with approximate e.s.d.) = 13.90 (0.15) * 0.0253 (0.0013) N2 * -0.0235 (0.0013) N3 * -0.0077 (0.0018) C2 * 0.0162 (0.0018) N4 * 0.0183 (0.0013) C16 * -0.0286 (0.0012) C17 Rms deviation of fitted atoms = 0.0211 |
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 | ||
Br1 | 0.028605 (11) | 0.86351 (2) | 0.124090 (18) | 0.02963 (10) | |
S1 | 0.21099 (2) | 0.04553 (5) | 0.17637 (4) | 0.01704 (13) | |
O1 | 0.18796 (7) | −0.08450 (16) | 0.18409 (11) | 0.0244 (4) | |
O2 | 0.26191 (7) | 0.07917 (17) | 0.24062 (10) | 0.0229 (4) | |
O3 | 0.02529 (7) | 0.18241 (17) | 0.13212 (12) | 0.0272 (4) | |
N1 | 0.15759 (8) | 0.15331 (17) | 0.19136 (12) | 0.0179 (4) | |
N2 | 0.21947 (8) | 0.07684 (19) | 0.07974 (12) | 0.0204 (4) | |
N3 | 0.13013 (8) | 0.20240 (18) | 0.03683 (12) | 0.0178 (4) | |
N4 | 0.19020 (8) | 0.15663 (18) | −0.06136 (12) | 0.0181 (4) | |
C1 | 0.12216 (9) | 0.2044 (2) | 0.11842 (14) | 0.0163 (4) | |
C2 | 0.18025 (10) | 0.1426 (2) | 0.02070 (15) | 0.0172 (4) | |
C3 | 0.06374 (9) | 0.2613 (2) | 0.13006 (14) | 0.0181 (4) | |
C4 | 0.05642 (10) | 0.4068 (2) | 0.13125 (15) | 0.0183 (4) | |
C5 | 0.00018 (10) | 0.4591 (2) | 0.11523 (18) | 0.0269 (5) | |
H5 | −0.0324 | 0.4013 | 0.106 | 0.032* | |
C6 | −0.00818 (11) | 0.5939 (2) | 0.11274 (19) | 0.0300 (6) | |
H6 | −0.0464 | 0.6297 | 0.0998 | 0.036* | |
C7 | 0.03997 (11) | 0.6772 (2) | 0.12937 (15) | 0.0229 (5) | |
C8 | 0.09632 (10) | 0.6279 (2) | 0.14851 (15) | 0.0202 (5) | |
H8 | 0.1287 | 0.6861 | 0.1616 | 0.024* | |
C9 | 0.10425 (10) | 0.4920 (2) | 0.14814 (15) | 0.0188 (5) | |
H9 | 0.1425 | 0.4565 | 0.1595 | 0.023* | |
C10 | 0.14928 (9) | 0.1735 (2) | 0.28200 (14) | 0.0169 (4) | |
C11 | 0.18390 (10) | 0.2672 (2) | 0.33372 (16) | 0.0243 (5) | |
H11 | 0.2103 | 0.3199 | 0.309 | 0.029* | |
C12 | 0.17929 (11) | 0.2827 (2) | 0.42197 (17) | 0.0297 (6) | |
H12 | 0.2024 | 0.3472 | 0.4581 | 0.036* | |
C13 | 0.14131 (11) | 0.2047 (3) | 0.45790 (16) | 0.0273 (5) | |
H13 | 0.1391 | 0.2141 | 0.519 | 0.033* | |
C14 | 0.10635 (10) | 0.1125 (2) | 0.40482 (17) | 0.0247 (5) | |
H14 | 0.0796 | 0.0606 | 0.4294 | 0.03* | |
C15 | 0.11032 (10) | 0.0960 (2) | 0.31654 (16) | 0.0196 (5) | |
H15 | 0.0867 | 0.0326 | 0.2801 | 0.023* | |
C16 | 0.15046 (11) | 0.2303 (2) | −0.13086 (15) | 0.0253 (5) | |
H16A | 0.1105 | 0.2002 | −0.1332 | 0.038* | |
H16B | 0.1611 | 0.2147 | −0.1888 | 0.038* | |
H16C | 0.1533 | 0.3251 | −0.117 | 0.038* | |
C17 | 0.24079 (10) | 0.0914 (2) | −0.08552 (15) | 0.0210 (5) | |
H17A | 0.2747 | 0.1021 | −0.0368 | 0.031* | |
H17B | 0.249 | 0.1316 | −0.1401 | 0.031* | |
H17C | 0.2325 | −0.0031 | −0.0958 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03008 (15) | 0.01636 (13) | 0.04118 (17) | 0.00559 (10) | 0.00403 (11) | −0.00394 (10) |
S1 | 0.0161 (3) | 0.0158 (3) | 0.0201 (3) | 0.0041 (2) | 0.0057 (2) | 0.0027 (2) |
O1 | 0.0276 (9) | 0.0156 (8) | 0.0327 (10) | 0.0017 (7) | 0.0126 (7) | 0.0029 (7) |
O2 | 0.0181 (8) | 0.0293 (9) | 0.0214 (8) | 0.0037 (7) | 0.0039 (7) | 0.0020 (7) |
O3 | 0.0190 (8) | 0.0190 (8) | 0.0437 (11) | −0.0016 (7) | 0.0064 (8) | 0.0002 (7) |
N1 | 0.0174 (9) | 0.0177 (9) | 0.0192 (9) | 0.0048 (7) | 0.0053 (7) | 0.0014 (7) |
N2 | 0.0208 (10) | 0.0200 (10) | 0.0214 (10) | 0.0079 (8) | 0.0068 (8) | 0.0020 (8) |
N3 | 0.0162 (9) | 0.0172 (9) | 0.0202 (10) | 0.0013 (7) | 0.0043 (7) | 0.0006 (7) |
N4 | 0.0194 (9) | 0.0183 (9) | 0.0177 (9) | 0.0021 (7) | 0.0061 (8) | −0.0002 (7) |
C1 | 0.0136 (10) | 0.0126 (10) | 0.0228 (12) | −0.0006 (8) | 0.0038 (8) | 0.0000 (8) |
C2 | 0.0180 (11) | 0.0124 (10) | 0.0217 (11) | −0.0015 (8) | 0.0049 (9) | −0.0022 (8) |
C3 | 0.0158 (10) | 0.0198 (11) | 0.0185 (11) | 0.0015 (9) | 0.0028 (9) | −0.0008 (9) |
C4 | 0.0192 (11) | 0.0175 (10) | 0.0188 (11) | 0.0016 (9) | 0.0049 (9) | −0.0015 (9) |
C5 | 0.0168 (11) | 0.0224 (12) | 0.0413 (15) | 0.0002 (9) | 0.0051 (10) | −0.0051 (11) |
C6 | 0.0173 (12) | 0.0230 (12) | 0.0482 (16) | 0.0057 (10) | 0.0031 (11) | −0.0060 (11) |
C7 | 0.0285 (13) | 0.0147 (10) | 0.0257 (13) | 0.0049 (9) | 0.0059 (10) | −0.0035 (9) |
C8 | 0.0209 (11) | 0.0186 (11) | 0.0215 (12) | −0.0020 (9) | 0.0050 (9) | −0.0015 (9) |
C9 | 0.0162 (10) | 0.0206 (11) | 0.0204 (11) | 0.0031 (9) | 0.0057 (9) | 0.0006 (9) |
C10 | 0.0175 (10) | 0.0152 (10) | 0.0185 (11) | 0.0046 (8) | 0.0049 (9) | 0.0007 (8) |
C11 | 0.0254 (12) | 0.0199 (11) | 0.0286 (13) | −0.0052 (10) | 0.0077 (10) | −0.0009 (10) |
C12 | 0.0363 (14) | 0.0248 (13) | 0.0270 (13) | −0.0032 (11) | 0.0039 (11) | −0.0062 (10) |
C13 | 0.0335 (14) | 0.0308 (13) | 0.0188 (12) | 0.0085 (11) | 0.0082 (10) | −0.0014 (10) |
C14 | 0.0196 (11) | 0.0287 (13) | 0.0289 (13) | 0.0039 (10) | 0.0124 (10) | 0.0047 (10) |
C15 | 0.0156 (11) | 0.0177 (10) | 0.0256 (12) | 0.0001 (9) | 0.0046 (9) | −0.0006 (9) |
C16 | 0.0282 (13) | 0.0292 (13) | 0.0185 (12) | 0.0057 (10) | 0.0052 (10) | 0.0032 (10) |
C17 | 0.0226 (12) | 0.0213 (11) | 0.0212 (12) | 0.0024 (9) | 0.0096 (9) | −0.0021 (9) |
Br1—C7 | 1.899 (2) | C7—C8 | 1.387 (3) |
S1—O2 | 1.4272 (17) | C8—C9 | 1.385 (3) |
S1—O1 | 1.4335 (17) | C8—H8 | 0.95 |
S1—N2 | 1.5614 (19) | C9—H9 | 0.95 |
S1—N1 | 1.7087 (18) | C10—C15 | 1.385 (3) |
O3—C3 | 1.209 (3) | C10—C11 | 1.387 (3) |
N1—C1 | 1.352 (3) | C11—C12 | 1.383 (3) |
N1—C10 | 1.451 (3) | C11—H11 | 0.95 |
N2—C2 | 1.330 (3) | C12—C13 | 1.382 (4) |
N3—C1 | 1.298 (3) | C12—H12 | 0.95 |
N3—C2 | 1.386 (3) | C13—C14 | 1.389 (4) |
N4—C2 | 1.328 (3) | C13—H13 | 0.95 |
N4—C17 | 1.467 (3) | C14—C15 | 1.381 (3) |
N4—C16 | 1.468 (3) | C14—H14 | 0.95 |
C1—C3 | 1.528 (3) | C15—H15 | 0.95 |
C3—C4 | 1.479 (3) | C16—H16A | 0.98 |
C4—C5 | 1.396 (3) | C16—H16B | 0.98 |
C4—C9 | 1.396 (3) | C16—H16C | 0.98 |
C5—C6 | 1.375 (3) | C17—H17A | 0.98 |
C5—H5 | 0.95 | C17—H17B | 0.98 |
C6—C7 | 1.390 (3) | C17—H17C | 0.98 |
C6—H6 | 0.95 | ||
O2—S1—O1 | 116.01 (10) | C9—C8—H8 | 120.7 |
O2—S1—N2 | 110.84 (10) | C7—C8—H8 | 120.7 |
O1—S1—N2 | 112.61 (10) | C8—C9—C4 | 120.5 (2) |
O2—S1—N1 | 106.91 (10) | C8—C9—H9 | 119.7 |
O1—S1—N1 | 105.91 (9) | C4—C9—H9 | 119.7 |
N2—S1—N1 | 103.48 (9) | C15—C10—C11 | 121.6 (2) |
C1—N1—C10 | 123.78 (18) | C15—C10—N1 | 120.6 (2) |
C1—N1—S1 | 118.57 (15) | C11—C10—N1 | 117.71 (19) |
C10—N1—S1 | 117.32 (14) | C12—C11—C10 | 118.8 (2) |
C2—N2—S1 | 122.78 (16) | C12—C11—H11 | 120.6 |
C1—N3—C2 | 117.87 (19) | C10—C11—H11 | 120.6 |
C2—N4—C17 | 119.53 (19) | C13—C12—C11 | 120.3 (2) |
C2—N4—C16 | 122.12 (18) | C13—C12—H12 | 119.8 |
C17—N4—C16 | 118.27 (18) | C11—C12—H12 | 119.8 |
N3—C1—N1 | 127.14 (19) | C12—C13—C14 | 120.1 (2) |
N3—C1—C3 | 114.97 (18) | C12—C13—H13 | 119.9 |
N1—C1—C3 | 117.70 (18) | C14—C13—H13 | 119.9 |
N4—C2—N2 | 117.77 (19) | C15—C14—C13 | 120.3 (2) |
N4—C2—N3 | 115.86 (19) | C15—C14—H14 | 119.9 |
N2—C2—N3 | 126.3 (2) | C13—C14—H14 | 119.9 |
O3—C3—C4 | 124.4 (2) | C14—C15—C10 | 118.8 (2) |
O3—C3—C1 | 116.5 (2) | C14—C15—H15 | 120.6 |
C4—C3—C1 | 118.95 (18) | C10—C15—H15 | 120.6 |
C5—C4—C9 | 119.7 (2) | N4—C16—H16A | 109.5 |
C5—C4—C3 | 118.8 (2) | N4—C16—H16B | 109.5 |
C9—C4—C3 | 121.6 (2) | H16A—C16—H16B | 109.5 |
C6—C5—C4 | 120.2 (2) | N4—C16—H16C | 109.5 |
C6—C5—H5 | 119.9 | H16A—C16—H16C | 109.5 |
C4—C5—H5 | 119.9 | H16B—C16—H16C | 109.5 |
C5—C6—C7 | 119.2 (2) | N4—C17—H17A | 109.5 |
C5—C6—H6 | 120.4 | N4—C17—H17B | 109.5 |
C7—C6—H6 | 120.4 | H17A—C17—H17B | 109.5 |
C8—C7—C6 | 121.7 (2) | N4—C17—H17C | 109.5 |
C8—C7—Br1 | 118.94 (18) | H17A—C17—H17C | 109.5 |
C6—C7—Br1 | 119.32 (18) | H17B—C17—H17C | 109.5 |
C9—C8—C7 | 118.5 (2) | ||
O2—S1—N1—C1 | 138.49 (16) | O3—C3—C4—C5 | −13.9 (4) |
O1—S1—N1—C1 | −97.24 (17) | C1—C3—C4—C5 | 161.2 (2) |
N2—S1—N1—C1 | 21.41 (19) | O3—C3—C4—C9 | 165.9 (2) |
O2—S1—N1—C10 | −47.84 (18) | C1—C3—C4—C9 | −19.0 (3) |
O1—S1—N1—C10 | 76.43 (17) | C9—C4—C5—C6 | 2.4 (4) |
N2—S1—N1—C10 | −164.92 (16) | C3—C4—C5—C6 | −177.7 (2) |
O2—S1—N2—C2 | −131.98 (19) | C4—C5—C6—C7 | −2.2 (4) |
O1—S1—N2—C2 | 96.20 (19) | C5—C6—C7—C8 | 0.0 (4) |
N1—S1—N2—C2 | −17.7 (2) | C5—C6—C7—Br1 | 179.0 (2) |
C2—N3—C1—N1 | −0.3 (3) | C6—C7—C8—C9 | 2.0 (4) |
C2—N3—C1—C3 | −175.08 (18) | Br1—C7—C8—C9 | −177.04 (17) |
C10—N1—C1—N3 | 172.2 (2) | C7—C8—C9—C4 | −1.7 (3) |
S1—N1—C1—N3 | −14.6 (3) | C5—C4—C9—C8 | −0.5 (3) |
C10—N1—C1—C3 | −13.2 (3) | C3—C4—C9—C8 | 179.7 (2) |
S1—N1—C1—C3 | 160.03 (15) | C1—N1—C10—C15 | 82.2 (3) |
C17—N4—C2—N2 | 4.7 (3) | S1—N1—C10—C15 | −91.1 (2) |
C16—N4—C2—N2 | −178.4 (2) | C1—N1—C10—C11 | −101.3 (3) |
C17—N4—C2—N3 | −177.18 (19) | S1—N1—C10—C11 | 85.4 (2) |
C16—N4—C2—N3 | −0.3 (3) | C15—C10—C11—C12 | 0.3 (4) |
S1—N2—C2—N4 | −175.90 (16) | N1—C10—C11—C12 | −176.2 (2) |
S1—N2—C2—N3 | 6.2 (3) | C10—C11—C12—C13 | 0.8 (4) |
C1—N3—C2—N4 | −172.18 (19) | C11—C12—C13—C14 | −1.7 (4) |
C1—N3—C2—N2 | 5.7 (3) | C12—C13—C14—C15 | 1.6 (4) |
N3—C1—C3—O3 | 95.5 (2) | C13—C14—C15—C10 | −0.5 (3) |
N1—C1—C3—O3 | −79.7 (3) | C11—C10—C15—C14 | −0.4 (3) |
N3—C1—C3—C4 | −80.0 (3) | N1—C10—C15—C14 | 175.9 (2) |
N1—C1—C3—C4 | 104.7 (2) |
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