Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805002308/sj6044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805002308/sj6044Isup2.hkl |
CCDC reference: 269862
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.121
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1 .. N3 .. 2.86 Ang.
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.734 0.950 Tmin' and Tmax expected: 0.936 0.953 RR' = 0.786 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.79 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C6 - C7 .. 5.14 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT431_ALERT_2_C Short Inter HL..A Contact F1 .. O3 .. 2.96 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: WinGX (Farrugia, 1999) and SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C14H9F3N4O5S | F(000) = 816 |
Mr = 402.31 | Dx = 1.638 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.8629 (14) Å | Cell parameters from 932 reflections |
b = 18.290 (5) Å | θ = 2.5–23.1° |
c = 18.403 (6) Å | µ = 0.27 mm−1 |
β = 94.642 (6)° | T = 293 K |
V = 1631.5 (8) Å3 | Block, yellow |
Z = 4 | 0.24 × 0.22 × 0.18 mm |
Bruker SMART CCD area-detector diffractometer | 3324 independent reflections |
Radiation source: fine-focus sealed tube | 1853 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker 1999) | h = −6→4 |
Tmin = 0.734, Tmax = 0.950 | k = −21→22 |
9336 measured reflections | l = −22→17 |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3 |
3324 reflections | (Δ/σ)max = 0.001 |
248 parameters | Δρmax = 0.20 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
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 | ||
S1 | 0.26536 (17) | 0.59060 (4) | 0.01699 (5) | 0.0593 (3) | |
N1 | 1.0099 (4) | 0.61478 (12) | 0.28509 (12) | 0.0445 (6) | |
N2 | 1.1383 (5) | 0.56043 (12) | 0.24978 (13) | 0.0444 (6) | |
H2 | 1.071 (5) | 0.5438 (13) | 0.2083 (8) | 0.043 (8)* | |
N3 | 1.3797 (5) | 0.43182 (12) | 0.18501 (13) | 0.0452 (6) | |
N4 | 1.9500 (6) | 0.39718 (14) | 0.41102 (18) | 0.0625 (7) | |
O1 | 0.6789 (4) | 0.55653 (11) | 0.14051 (12) | 0.0616 (6) | |
O2 | 1.1687 (4) | 0.45632 (11) | 0.15310 (11) | 0.0626 (6) | |
O3 | 1.5248 (4) | 0.38646 (11) | 0.15907 (11) | 0.0597 (6) | |
O4 | 2.0824 (5) | 0.35260 (13) | 0.37838 (15) | 0.0847 (8) | |
O5 | 1.9886 (6) | 0.40902 (13) | 0.47591 (15) | 0.0905 (9) | |
C1 | 0.6728 (5) | 0.62089 (15) | 0.12344 (15) | 0.0427 (7) | |
C2 | 0.8751 (5) | 0.67286 (14) | 0.16468 (16) | 0.0449 (7) | |
H2A | 1.0583 | 0.6646 | 0.1490 | 0.054* | |
H2B | 0.8231 | 0.7228 | 0.1524 | 0.054* | |
C3 | 0.8834 (5) | 0.66341 (14) | 0.24548 (16) | 0.0414 (7) | |
C4 | 0.7468 (6) | 0.72131 (16) | 0.28682 (19) | 0.0539 (8) | |
C5 | 0.4844 (5) | 0.64945 (14) | 0.06589 (15) | 0.0415 (7) | |
C6 | 0.4388 (5) | 0.72136 (15) | 0.04309 (15) | 0.0482 (7) | |
H6 | 0.5372 | 0.7614 | 0.0624 | 0.058* | |
C7 | 0.2268 (7) | 0.72560 (18) | −0.01237 (18) | 0.0653 (9) | |
H7 | 0.1683 | 0.7693 | −0.0344 | 0.078* | |
C8 | 0.1156 (6) | 0.66048 (18) | −0.03076 (17) | 0.0635 (9) | |
H8 | −0.0298 | 0.6545 | −0.0663 | 0.076* | |
C9 | 1.3284 (5) | 0.51794 (13) | 0.28941 (15) | 0.0398 (6) | |
C10 | 1.4582 (5) | 0.45758 (13) | 0.25925 (14) | 0.0381 (6) | |
C11 | 1.6608 (5) | 0.41893 (13) | 0.29839 (16) | 0.0438 (7) | |
H11 | 1.7464 | 0.3797 | 0.2774 | 0.053* | |
C12 | 1.7354 (5) | 0.43880 (15) | 0.36862 (16) | 0.0472 (7) | |
C13 | 1.6113 (6) | 0.49691 (15) | 0.40072 (16) | 0.0512 (7) | |
H13 | 1.6629 | 0.5094 | 0.4489 | 0.061* | |
C14 | 1.4123 (6) | 0.53598 (15) | 0.36134 (16) | 0.0489 (7) | |
H14 | 1.3308 | 0.5755 | 0.3830 | 0.059* | |
F1 | 0.8787 (4) | 0.78430 (9) | 0.28437 (12) | 0.0814 (6) | |
F2 | 0.4922 (3) | 0.73378 (11) | 0.25704 (12) | 0.0893 (7) | |
F3 | 0.7260 (4) | 0.70662 (11) | 0.35590 (12) | 0.0908 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0668 (5) | 0.0585 (5) | 0.0519 (5) | −0.0079 (4) | 0.0010 (4) | −0.0128 (4) |
N1 | 0.0421 (13) | 0.0428 (13) | 0.0489 (15) | 0.0022 (10) | 0.0062 (11) | −0.0072 (11) |
N2 | 0.0497 (14) | 0.0411 (14) | 0.0414 (15) | 0.0061 (11) | −0.0015 (12) | −0.0074 (12) |
N3 | 0.0552 (15) | 0.0322 (13) | 0.0489 (15) | −0.0073 (12) | 0.0091 (13) | −0.0031 (11) |
N4 | 0.0661 (17) | 0.0428 (16) | 0.075 (2) | 0.0001 (13) | −0.0139 (16) | 0.0074 (15) |
O1 | 0.0671 (13) | 0.0420 (12) | 0.0729 (15) | −0.0115 (10) | −0.0106 (11) | 0.0057 (11) |
O2 | 0.0635 (13) | 0.0589 (13) | 0.0621 (14) | 0.0066 (11) | −0.0145 (12) | −0.0167 (11) |
O3 | 0.0762 (14) | 0.0478 (12) | 0.0572 (14) | 0.0082 (10) | 0.0180 (11) | −0.0097 (10) |
O4 | 0.0894 (17) | 0.0660 (16) | 0.095 (2) | 0.0303 (14) | −0.0138 (15) | 0.0034 (14) |
O5 | 0.119 (2) | 0.0778 (17) | 0.0676 (18) | 0.0137 (14) | −0.0358 (17) | 0.0008 (14) |
C1 | 0.0389 (15) | 0.0406 (17) | 0.0495 (18) | −0.0069 (12) | 0.0088 (13) | −0.0033 (14) |
C2 | 0.0395 (14) | 0.0393 (15) | 0.056 (2) | −0.0027 (12) | 0.0041 (13) | −0.0004 (13) |
C3 | 0.0327 (13) | 0.0362 (15) | 0.055 (2) | −0.0030 (12) | 0.0024 (13) | −0.0073 (13) |
C4 | 0.0467 (18) | 0.0489 (19) | 0.067 (2) | 0.0033 (15) | 0.0093 (16) | −0.0153 (17) |
C5 | 0.0373 (14) | 0.0476 (17) | 0.0402 (17) | −0.0033 (12) | 0.0066 (12) | −0.0041 (13) |
C6 | 0.0443 (16) | 0.0507 (18) | 0.0488 (19) | −0.0014 (13) | −0.0015 (14) | −0.0001 (14) |
C7 | 0.081 (2) | 0.055 (2) | 0.058 (2) | 0.0057 (17) | −0.0088 (18) | 0.0024 (17) |
C8 | 0.0636 (19) | 0.079 (2) | 0.046 (2) | 0.0055 (18) | −0.0079 (16) | −0.0124 (16) |
C9 | 0.0397 (15) | 0.0363 (15) | 0.0435 (17) | −0.0030 (12) | 0.0044 (13) | −0.0011 (13) |
C10 | 0.0418 (15) | 0.0320 (14) | 0.0408 (16) | −0.0062 (12) | 0.0042 (13) | −0.0025 (12) |
C11 | 0.0449 (15) | 0.0302 (14) | 0.057 (2) | −0.0019 (12) | 0.0090 (14) | 0.0001 (13) |
C12 | 0.0483 (16) | 0.0398 (16) | 0.052 (2) | −0.0020 (13) | −0.0030 (15) | 0.0044 (14) |
C13 | 0.0600 (18) | 0.0511 (18) | 0.0415 (18) | −0.0025 (15) | −0.0026 (15) | −0.0051 (15) |
C14 | 0.0556 (17) | 0.0417 (16) | 0.0497 (19) | 0.0059 (14) | 0.0049 (15) | −0.0068 (14) |
F1 | 0.0768 (12) | 0.0466 (11) | 0.1229 (18) | −0.0079 (9) | 0.0212 (11) | −0.0293 (11) |
F2 | 0.0477 (10) | 0.0907 (14) | 0.1277 (19) | 0.0201 (10) | −0.0035 (11) | −0.0373 (13) |
F3 | 0.1211 (17) | 0.0845 (14) | 0.0714 (15) | 0.0267 (12) | 0.0358 (13) | −0.0157 (12) |
S1—C8 | 1.683 (3) | C4—F3 | 1.311 (4) |
S1—C5 | 1.717 (3) | C4—F1 | 1.321 (3) |
N1—C3 | 1.276 (3) | C4—F2 | 1.333 (3) |
N1—N2 | 1.366 (3) | C5—C6 | 1.393 (4) |
N2—C9 | 1.371 (3) | C6—C7 | 1.393 (4) |
N2—H2 | 0.862 (10) | C6—H6 | 0.9300 |
N3—O3 | 1.212 (3) | C7—C8 | 1.340 (4) |
N3—O2 | 1.225 (3) | C7—H7 | 0.9300 |
N3—C10 | 1.466 (3) | C8—H8 | 0.9300 |
N4—O5 | 1.213 (3) | C9—C14 | 1.393 (4) |
N4—O4 | 1.226 (3) | C9—C10 | 1.408 (3) |
N4—C12 | 1.465 (4) | C10—C11 | 1.369 (3) |
O1—C1 | 1.218 (3) | C11—C12 | 1.363 (4) |
C1—C5 | 1.441 (4) | C11—H11 | 0.9300 |
C1—C2 | 1.525 (3) | C12—C13 | 1.379 (4) |
C2—C3 | 1.494 (4) | C13—C14 | 1.363 (4) |
C2—H2A | 0.9700 | C13—H13 | 0.9300 |
C2—H2B | 0.9700 | C14—H14 | 0.9300 |
C3—C4 | 1.491 (4) | ||
C8—S1—C5 | 91.23 (14) | C6—C5—S1 | 110.9 (2) |
C3—N1—N2 | 117.0 (2) | C1—C5—S1 | 119.2 (2) |
N1—N2—C9 | 118.3 (2) | C5—C6—C7 | 111.3 (3) |
N1—N2—H2 | 121.5 (17) | C5—C6—H6 | 124.3 |
C9—N2—H2 | 117.6 (17) | C7—C6—H6 | 124.3 |
O3—N3—O2 | 123.6 (2) | C8—C7—C6 | 113.3 (3) |
O3—N3—C10 | 118.1 (2) | C8—C7—H7 | 123.4 |
O2—N3—C10 | 118.3 (2) | C6—C7—H7 | 123.4 |
O5—N4—O4 | 123.7 (3) | C7—C8—S1 | 113.2 (2) |
O5—N4—C12 | 118.6 (3) | C7—C8—H8 | 123.4 |
O4—N4—C12 | 117.7 (3) | S1—C8—H8 | 123.4 |
O1—C1—C5 | 122.7 (2) | N2—C9—C14 | 120.3 (2) |
O1—C1—C2 | 118.2 (2) | N2—C9—C10 | 122.6 (2) |
C5—C1—C2 | 119.1 (2) | C14—C9—C10 | 117.0 (2) |
C3—C2—C1 | 112.8 (2) | C11—C10—C9 | 121.6 (2) |
C3—C2—H2A | 109.0 | C11—C10—N3 | 116.5 (2) |
C1—C2—H2A | 109.0 | C9—C10—N3 | 121.9 (2) |
C3—C2—H2B | 109.0 | C12—C11—C10 | 119.1 (3) |
C1—C2—H2B | 109.0 | C12—C11—H11 | 120.5 |
H2A—C2—H2B | 107.8 | C10—C11—H11 | 120.5 |
N1—C3—C4 | 114.7 (3) | C11—C12—C13 | 121.3 (3) |
N1—C3—C2 | 128.5 (2) | C11—C12—N4 | 119.3 (3) |
C4—C3—C2 | 116.6 (2) | C13—C12—N4 | 119.3 (3) |
F3—C4—F1 | 106.7 (3) | C14—C13—C12 | 119.5 (3) |
F3—C4—F2 | 107.0 (3) | C14—C13—H13 | 120.2 |
F1—C4—F2 | 105.9 (2) | C12—C13—H13 | 120.2 |
F3—C4—C3 | 114.9 (3) | C13—C14—C9 | 121.5 (3) |
F1—C4—C3 | 111.4 (2) | C13—C14—H14 | 119.3 |
F2—C4—C3 | 110.4 (2) | C9—C14—H14 | 119.3 |
C6—C5—C1 | 129.8 (2) | ||
C3—N1—N2—C9 | 164.7 (2) | N1—N2—C9—C14 | −8.0 (4) |
O1—C1—C2—C3 | −47.4 (3) | N1—N2—C9—C10 | 175.7 (2) |
C5—C1—C2—C3 | 133.0 (2) | N2—C9—C10—C11 | 175.5 (2) |
N2—N1—C3—C4 | 179.9 (2) | C14—C9—C10—C11 | −0.9 (4) |
N2—N1—C3—C2 | −5.6 (4) | N2—C9—C10—N3 | −5.9 (4) |
C1—C2—C3—N1 | 79.7 (3) | C14—C9—C10—N3 | 177.7 (2) |
C1—C2—C3—C4 | −106.0 (3) | O3—N3—C10—C11 | −11.5 (3) |
N1—C3—C4—F3 | −13.5 (4) | O2—N3—C10—C11 | 167.3 (2) |
C2—C3—C4—F3 | 171.4 (2) | O3—N3—C10—C9 | 169.8 (2) |
N1—C3—C4—F1 | 108.0 (3) | O2—N3—C10—C9 | −11.4 (4) |
C2—C3—C4—F1 | −67.1 (3) | C9—C10—C11—C12 | 1.0 (4) |
N1—C3—C4—F2 | −134.6 (3) | N3—C10—C11—C12 | −177.7 (2) |
C2—C3—C4—F2 | 50.3 (3) | C10—C11—C12—C13 | −0.1 (4) |
O1—C1—C5—C6 | 175.3 (3) | C10—C11—C12—N4 | 179.4 (2) |
C2—C1—C5—C6 | −5.2 (4) | O5—N4—C12—C11 | −170.3 (3) |
O1—C1—C5—S1 | −2.1 (4) | O4—N4—C12—C11 | 10.4 (4) |
C2—C1—C5—S1 | 177.54 (19) | O5—N4—C12—C13 | 9.2 (4) |
C8—S1—C5—C6 | −1.0 (2) | O4—N4—C12—C13 | −170.2 (3) |
C8—S1—C5—C1 | 176.8 (2) | C11—C12—C13—C14 | −0.8 (4) |
C1—C5—C6—C7 | −176.9 (3) | N4—C12—C13—C14 | 179.7 (2) |
S1—C5—C6—C7 | 0.6 (3) | C12—C13—C14—C9 | 0.9 (4) |
C5—C6—C7—C8 | 0.3 (4) | N2—C9—C14—C13 | −176.5 (2) |
C6—C7—C8—S1 | −1.1 (4) | C10—C9—C14—C13 | 0.0 (4) |
C5—S1—C8—C7 | 1.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2 | 0.86 (1) | 1.97 (2) | 2.619 (3) | 131 (2) |
N2—H2···O1 | 0.86 (1) | 2.21 (2) | 2.883 (3) | 135 (2) |
C2—H2B···O4i | 0.97 | 2.49 | 3.392 (4) | 154 |
C13—H13···O5ii | 0.93 | 2.58 | 3.345 (4) | 140 |
Symmetry codes: (i) −x+3, y+1/2, −z+1/2; (ii) −x+4, −y+1, −z+1. |
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