Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803026369/tk6140sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803026369/tk6140Isup2.hkl |
CCDC reference: 232164
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.043
- wR factor = 0.152
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 34 Perc. PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg. PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.62 Ratio
Alert level C PLAT213_ALERT_2_C Atom C35A has ADP max/min Ratio ............. 3.10 prolat PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.66 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C64 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C62 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
0 ALERT level A = In general: serious problem 3 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 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SDP (Frenz, 1985); cell refinement: SDP; data reduction: WinGX (Farrugia, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97; molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.
C21H23ClN2O7S2 | F(000) = 1072 |
Mr = 514.98 | Dx = 1.420 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 8.546 (4) Å | θ = 10–12° |
b = 24.166 (3) Å | µ = 0.38 mm−1 |
c = 12.057 (8) Å | T = 293 K |
β = 104.67 (2)° | Plate, colourless |
V = 2409 (2) Å3 | 0.3 × 0.05 × 0.05 mm |
Z = 4 |
Enraf-Nonius CAD-4 diffractometer | 1419 reflections with I > 2σ(I) |
Radiation source: Enraf-Nonius FR590 | Rint = 0.037 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
ω–2θ scans | h = −4→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→28 |
Tmin = 0.933, Tmax = 0.979 | l = −14→13 |
4570 measured reflections | 3 standard reflections every 120 min |
4233 independent reflections | intensity decay: none |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.152 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0626P)2] where P = (Fo2 + 2Fc2)/3 |
4570 reflections | (Δ/σ)max = 0.011 |
307 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | 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. Data were collected on a CAD4, and were corrected for absorption using the psi scan method. The general bond precision is low due to the lack of intense data. The space group P21/n is a sub-group of P21/c (a=8.546, b=24.166 and c=12.892 Å and β=115.22°. The structure was solved with SHELX97 direct methods and refined using SHELX97. 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) | |
N1 | −0.1040 (5) | 0.94155 (18) | 0.4778 (4) | 0.0471 (13) | |
H1 | −0.1942 | 0.9555 | 0.4834 | 0.057* | |
C11 | −0.0755 (7) | 0.9428 (2) | 0.3677 (5) | 0.0394 (14) | |
C12 | 0.0761 (7) | 0.9305 (2) | 0.3494 (5) | 0.0456 (15) | |
H12 | 0.1645 | 0.9224 | 0.4100 | 0.055* | |
C13 | 0.0888 (7) | 0.9309 (2) | 0.2379 (5) | 0.0471 (15) | |
C14 | −0.0393 (8) | 0.9437 (2) | 0.1472 (5) | 0.0517 (16) | |
H14 | −0.0261 | 0.9440 | 0.0730 | 0.062* | |
C15 | −0.1869 (8) | 0.9563 (2) | 0.1663 (5) | 0.0481 (16) | |
C16 | −0.2035 (7) | 0.9566 (2) | 0.2776 (5) | 0.0479 (16) | |
H16 | −0.3021 | 0.9664 | 0.2915 | 0.057* | |
O131 | 0.2322 (5) | 0.92002 (18) | 0.2089 (3) | 0.0700 (13) | |
C132 | 0.3699 (8) | 0.9069 (3) | 0.2973 (6) | 0.092 (2) | |
H13A | 0.4080 | 0.9395 | 0.3411 | 0.137* | |
H13B | 0.4533 | 0.8928 | 0.2645 | 0.137* | |
H13C | 0.3421 | 0.8793 | 0.3464 | 0.137* | |
O151 | −0.3226 (5) | 0.96871 (18) | 0.0836 (3) | 0.0690 (13) | |
C152 | −0.3161 (9) | 0.9649 (3) | −0.0333 (5) | 0.088 (2) | |
H15A | −0.2334 | 0.9891 | −0.0461 | 0.132* | |
H15B | −0.4187 | 0.9754 | −0.0824 | 0.132* | |
H15C | −0.2917 | 0.9275 | −0.0501 | 0.132* | |
C2 | −0.0078 (7) | 0.9213 (2) | 0.5747 (5) | 0.0394 (14) | |
O21 | 0.1304 (5) | 0.90551 (17) | 0.5876 (3) | 0.0574 (11) | |
C3 | −0.0822 (6) | 0.9196 (2) | 0.6789 (4) | 0.0367 (14) | |
H3 | −0.0496 | 0.9545 | 0.7194 | 0.044* | |
C31 | −0.2671 (7) | 0.9183 (3) | 0.6556 (5) | 0.0476 (16) | |
O32 | −0.3543 (5) | 0.94431 (19) | 0.5786 (4) | 0.0693 (13) | |
O33 | −0.3144 (4) | 0.88846 (16) | 0.7320 (3) | 0.0544 (11) | |
C34 | −0.4899 (7) | 0.8828 (3) | 0.7145 (6) | 0.080 (2) | |
H34A | −0.5300 | 0.9162 | 0.7423 | 0.096* | |
H34B | −0.5386 | 0.8807 | 0.6327 | 0.096* | |
C35A | −0.542 (2) | 0.8400 (9) | 0.764 (2) | 0.108 (8) | 0.40 |
H35A | −0.6564 | 0.8428 | 0.7534 | 0.161* | 0.40 |
H35B | −0.4889 | 0.8397 | 0.8441 | 0.161* | 0.40 |
H35C | −0.5168 | 0.8064 | 0.7293 | 0.161* | 0.40 |
C35B | −0.5431 (13) | 0.8330 (5) | 0.6535 (11) | 0.072 (4) | 0.60 |
H35D | −0.4865 | 0.8021 | 0.6954 | 0.109* | 0.60 |
H35E | −0.5214 | 0.8347 | 0.5793 | 0.109* | 0.60 |
H35F | −0.6572 | 0.8285 | 0.6448 | 0.109* | 0.60 |
C4 | 0.0059 (6) | 0.8744 (2) | 0.7615 (4) | 0.0366 (13) | |
S41 | 0.1266 (2) | 0.90242 (6) | 0.88475 (12) | 0.0534 (5) | |
C42 | 0.2217 (8) | 0.8431 (2) | 0.9638 (5) | 0.073 (2) | |
H42A | 0.1411 | 0.8158 | 0.9666 | 0.110* | |
H42B | 0.2761 | 0.8541 | 1.0404 | 0.110* | |
H42C | 0.2988 | 0.8277 | 0.9267 | 0.110* | |
N5 | 0.0009 (5) | 0.82191 (18) | 0.7487 (3) | 0.0411 (12) | |
S6 | −0.1041 (2) | 0.78915 (6) | 0.63448 (13) | 0.0485 (4) | |
O61 | −0.1868 (5) | 0.74531 (16) | 0.6750 (3) | 0.0664 (12) | |
O62 | −0.1973 (5) | 0.82527 (16) | 0.5484 (3) | 0.0568 (11) | |
C61 | 0.0529 (7) | 0.7610 (2) | 0.5797 (5) | 0.0484 (16) | |
C62 | 0.1610 (9) | 0.7212 (3) | 0.6350 (6) | 0.069 (2) | |
C63 | 0.2771 (11) | 0.7003 (3) | 0.5830 (10) | 0.110 (3) | |
H63 | 0.3518 | 0.6738 | 0.6192 | 0.132* | |
C64 | 0.2770 (13) | 0.7203 (5) | 0.4758 (10) | 0.133 (4) | |
H64 | 0.3525 | 0.7066 | 0.4393 | 0.160* | |
C65 | 0.1721 (12) | 0.7588 (4) | 0.4225 (7) | 0.105 (3) | |
H65 | 0.1765 | 0.7713 | 0.3504 | 0.126* | |
C66 | 0.0594 (8) | 0.7798 (3) | 0.4726 (6) | 0.069 (2) | |
H66 | −0.0129 | 0.8066 | 0.4351 | 0.083* | |
Cl62 | 0.1645 (3) | 0.69871 (7) | 0.77170 (18) | 0.0997 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.040 (3) | 0.065 (3) | 0.036 (3) | 0.013 (3) | 0.010 (3) | 0.011 (2) |
C11 | 0.041 (4) | 0.040 (3) | 0.039 (4) | −0.008 (3) | 0.013 (3) | −0.001 (3) |
C12 | 0.041 (4) | 0.053 (4) | 0.045 (4) | 0.000 (3) | 0.015 (3) | 0.006 (3) |
C13 | 0.050 (4) | 0.046 (4) | 0.052 (4) | 0.003 (3) | 0.024 (4) | 0.004 (3) |
C14 | 0.065 (5) | 0.050 (4) | 0.041 (4) | 0.000 (4) | 0.015 (4) | 0.000 (3) |
C15 | 0.049 (4) | 0.047 (4) | 0.043 (4) | −0.004 (3) | 0.003 (4) | −0.003 (3) |
C16 | 0.037 (4) | 0.058 (4) | 0.048 (4) | −0.003 (3) | 0.009 (3) | 0.002 (3) |
O131 | 0.059 (3) | 0.096 (4) | 0.065 (3) | 0.014 (3) | 0.034 (3) | 0.008 (3) |
C132 | 0.048 (5) | 0.129 (7) | 0.105 (6) | 0.010 (5) | 0.033 (5) | −0.001 (6) |
O151 | 0.066 (3) | 0.094 (3) | 0.041 (3) | 0.010 (3) | 0.003 (2) | 0.005 (2) |
C152 | 0.102 (6) | 0.115 (6) | 0.037 (4) | 0.007 (5) | −0.002 (4) | −0.010 (4) |
C2 | 0.042 (4) | 0.042 (3) | 0.037 (4) | −0.002 (3) | 0.014 (3) | 0.002 (3) |
O21 | 0.041 (2) | 0.086 (3) | 0.049 (3) | 0.014 (2) | 0.017 (2) | 0.017 (2) |
C3 | 0.035 (3) | 0.040 (3) | 0.033 (3) | 0.000 (3) | 0.005 (3) | −0.002 (3) |
C31 | 0.045 (4) | 0.060 (4) | 0.045 (4) | 0.003 (3) | 0.024 (3) | −0.013 (3) |
O32 | 0.045 (3) | 0.097 (3) | 0.066 (3) | 0.020 (3) | 0.013 (2) | 0.022 (3) |
O33 | 0.038 (2) | 0.072 (3) | 0.061 (3) | −0.007 (2) | 0.028 (2) | 0.003 (2) |
C34 | 0.039 (4) | 0.115 (7) | 0.094 (6) | −0.018 (4) | 0.031 (4) | −0.032 (5) |
C35A | 0.067 (15) | 0.13 (2) | 0.15 (2) | −0.006 (13) | 0.068 (15) | 0.060 (17) |
C35B | 0.033 (6) | 0.060 (8) | 0.118 (11) | 0.005 (6) | 0.008 (8) | 0.003 (8) |
C4 | 0.033 (3) | 0.046 (4) | 0.033 (3) | −0.006 (3) | 0.011 (3) | −0.001 (3) |
S41 | 0.0626 (11) | 0.0471 (9) | 0.0438 (9) | 0.0013 (9) | 0.0012 (8) | −0.0053 (8) |
C42 | 0.077 (5) | 0.072 (5) | 0.054 (4) | 0.014 (4) | −0.013 (4) | 0.005 (4) |
N5 | 0.050 (3) | 0.034 (3) | 0.040 (3) | −0.003 (2) | 0.013 (2) | −0.004 (2) |
S6 | 0.0517 (10) | 0.0486 (9) | 0.0473 (10) | −0.0099 (9) | 0.0163 (9) | −0.0107 (8) |
O61 | 0.075 (3) | 0.057 (3) | 0.074 (3) | −0.028 (3) | 0.030 (3) | −0.013 (2) |
O62 | 0.055 (3) | 0.063 (3) | 0.048 (2) | 0.003 (2) | 0.005 (2) | −0.010 (2) |
C61 | 0.056 (4) | 0.046 (4) | 0.048 (4) | −0.004 (3) | 0.020 (3) | −0.022 (3) |
C62 | 0.067 (5) | 0.044 (4) | 0.090 (5) | 0.005 (4) | 0.012 (4) | −0.016 (4) |
C63 | 0.080 (6) | 0.079 (6) | 0.166 (10) | 0.028 (5) | 0.022 (7) | −0.037 (7) |
C64 | 0.100 (8) | 0.167 (12) | 0.146 (11) | 0.022 (8) | 0.057 (8) | −0.053 (9) |
C65 | 0.118 (8) | 0.135 (8) | 0.072 (6) | −0.003 (7) | 0.041 (6) | −0.020 (6) |
C66 | 0.068 (5) | 0.086 (5) | 0.057 (5) | 0.007 (4) | 0.021 (4) | −0.030 (4) |
Cl62 | 0.1148 (17) | 0.0619 (12) | 0.1091 (16) | 0.0065 (12) | 0.0034 (14) | 0.0224 (11) |
N1—C2 | 1.339 (6) | C34—C35B | 1.424 (11) |
N1—C11 | 1.409 (6) | C34—H34A | 0.9700 |
N1—H1 | 0.8600 | C34—H34B | 0.9700 |
C11—C16 | 1.374 (7) | C35A—H35A | 0.9600 |
C11—C12 | 1.399 (7) | C35A—H35B | 0.9600 |
C12—C13 | 1.376 (7) | C35A—H35C | 0.9600 |
C12—H12 | 0.9300 | C35B—H35D | 0.9600 |
C13—C14 | 1.372 (7) | C35B—H35E | 0.9600 |
C13—O131 | 1.382 (6) | C35B—H35F | 0.9600 |
C14—C15 | 1.372 (7) | C4—N5 | 1.277 (6) |
C14—H14 | 0.9300 | C4—S41 | 1.719 (5) |
C15—O151 | 1.358 (6) | S41—C42 | 1.798 (5) |
C15—C16 | 1.385 (7) | C42—H42A | 0.9600 |
C16—H16 | 0.9300 | C42—H42B | 0.9600 |
O131—C132 | 1.409 (7) | C42—H42C | 0.9600 |
C132—H13A | 0.9600 | N5—S6 | 1.644 (4) |
C132—H13B | 0.9600 | S6—O61 | 1.427 (4) |
C132—H13C | 0.9600 | S6—O62 | 1.434 (4) |
O151—C152 | 1.427 (6) | S6—C61 | 1.774 (6) |
C152—H15A | 0.9600 | C61—C62 | 1.383 (8) |
C152—H15B | 0.9600 | C61—C66 | 1.383 (8) |
C152—H15C | 0.9600 | C62—C63 | 1.397 (10) |
C2—O21 | 1.213 (6) | C62—Cl62 | 1.728 (7) |
C2—C3 | 1.546 (6) | C63—C64 | 1.379 (11) |
C3—C31 | 1.533 (7) | C63—H63 | 0.9300 |
C3—C4 | 1.540 (7) | C64—C65 | 1.338 (11) |
C3—H3 | 0.9800 | C64—H64 | 0.9300 |
C31—O32 | 1.209 (6) | C65—C66 | 1.358 (9) |
C31—O33 | 1.312 (6) | C65—H65 | 0.9300 |
O33—C34 | 1.468 (6) | C66—H66 | 0.9300 |
C34—C35A | 1.323 (17) | ||
C2—N1—C11 | 128.0 (5) | O33—C34—H34A | 108.1 |
C2—N1—H1 | 116.0 | C35A—C34—H34B | 108.1 |
C11—N1—H1 | 116.0 | C35B—C34—H34B | 55.4 |
C16—C11—C12 | 120.7 (5) | O33—C34—H34B | 108.1 |
C16—C11—N1 | 117.2 (5) | H34A—C34—H34B | 107.3 |
C12—C11—N1 | 122.2 (5) | C34—C35A—H35A | 109.5 |
C13—C12—C11 | 117.3 (5) | C34—C35A—H35B | 109.5 |
C13—C12—H12 | 121.4 | H35A—C35A—H35B | 109.5 |
C11—C12—H12 | 121.4 | C34—C35A—H35C | 109.5 |
C14—C13—C12 | 122.4 (6) | H35A—C35A—H35C | 109.5 |
C14—C13—O131 | 114.9 (6) | H35B—C35A—H35C | 109.5 |
C12—C13—O131 | 122.7 (6) | C34—C35B—H35D | 109.5 |
C15—C14—C13 | 119.9 (6) | C34—C35B—H35E | 109.5 |
C15—C14—H14 | 120.1 | H35D—C35B—H35E | 109.5 |
C13—C14—H14 | 120.1 | C34—C35B—H35F | 109.5 |
O151—C15—C14 | 125.2 (6) | H35D—C35B—H35F | 109.5 |
O151—C15—C16 | 115.6 (6) | H35E—C35B—H35F | 109.5 |
C14—C15—C16 | 119.2 (6) | N5—C4—C3 | 129.1 (5) |
C11—C16—C15 | 120.5 (6) | N5—C4—S41 | 119.3 (4) |
C11—C16—H16 | 119.7 | C3—C4—S41 | 111.6 (4) |
C15—C16—H16 | 119.7 | C4—S41—C42 | 103.6 (3) |
C13—O131—C132 | 118.4 (5) | S41—C42—H42A | 109.5 |
O131—C132—H13A | 109.5 | S41—C42—H42B | 109.5 |
O131—C132—H13B | 109.5 | H42A—C42—H42B | 109.5 |
H13A—C132—H13B | 109.5 | S41—C42—H42C | 109.5 |
O131—C132—H13C | 109.5 | H42A—C42—H42C | 109.5 |
H13A—C132—H13C | 109.5 | H42B—C42—H42C | 109.5 |
H13B—C132—H13C | 109.5 | C4—N5—S6 | 125.0 (4) |
C15—O151—C152 | 118.1 (5) | O61—S6—O62 | 117.8 (3) |
O151—C152—H15A | 109.5 | O61—S6—N5 | 106.4 (2) |
O151—C152—H15B | 109.5 | O62—S6—N5 | 113.5 (2) |
H15A—C152—H15B | 109.5 | O61—S6—C61 | 109.3 (3) |
O151—C152—H15C | 109.5 | O62—S6—C61 | 107.3 (3) |
H15A—C152—H15C | 109.5 | N5—S6—C61 | 101.1 (3) |
H15B—C152—H15C | 109.5 | C62—C61—C66 | 119.9 (6) |
O21—C2—N1 | 126.1 (5) | C62—C61—S6 | 124.2 (5) |
O21—C2—C3 | 118.3 (5) | C66—C61—S6 | 115.8 (5) |
N1—C2—C3 | 115.6 (5) | C61—C62—C63 | 119.9 (7) |
C31—C3—C4 | 114.6 (5) | C61—C62—Cl62 | 121.8 (6) |
C31—C3—C2 | 117.9 (4) | C63—C62—Cl62 | 118.2 (7) |
C4—C3—C2 | 108.1 (4) | C64—C63—C62 | 117.5 (9) |
C31—C3—H3 | 105.0 | C64—C63—H63 | 121.2 |
C4—C3—H3 | 105.0 | C62—C63—H63 | 121.2 |
C2—C3—H3 | 105.0 | C65—C64—C63 | 122.4 (10) |
O32—C31—O33 | 125.9 (6) | C65—C64—H64 | 118.8 |
O32—C31—C3 | 122.4 (6) | C63—C64—H64 | 118.8 |
O33—C31—C3 | 111.6 (5) | C64—C65—C66 | 120.7 (9) |
C31—O33—C34 | 115.8 (5) | C64—C65—H65 | 119.7 |
C35A—C34—C35B | 58.1 (11) | C66—C65—H65 | 119.7 |
C35A—C34—O33 | 116.9 (11) | C65—C66—C61 | 119.6 (7) |
C35B—C34—O33 | 109.5 (7) | C65—C66—H66 | 120.2 |
C35A—C34—H34A | 108.1 | C61—C66—H66 | 120.2 |
C35B—C34—H34A | 142.1 | ||
C12—C11—N1—C2 | −11.3 (8) | C3—C4—N5—S6 | 1.0 (8) |
C11—N1—C2—C3 | −172.8 (5) | C4—N5—S6—C61 | 112.7 (5) |
N1—C2—C3—C4 | 155.6 (5) | N5—S6—C61—C62 | 65.8 (5) |
C2—C3—C4—N5 | −69.4 (7) |