Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006544/ac6234sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006544/ac6234Isup2.hkl |
CCDC reference: 601095
Key indicators
- Single-crystal X-ray study
- T = 84 K
- Mean (C-C) = 0.002 Å
- R factor = 0.022
- wR factor = 0.058
- Data-to-parameter ratio = 16.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.04 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.68 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 25
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 27.08 From the CIF: _reflns_number_total 3685 Count of symmetry unique reflns 2180 Completeness (_total/calc) 169.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1505 Fraction of Friedel pairs measured 0.690 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 5 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1995).
C18H23NO4S2 | F(000) = 404 |
Mr = 381.49 | Dx = 1.382 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8132 (1) Å | Cell parameters from 8192 reflections |
b = 7.3784 (1) Å | θ = 1.3–27.1° |
c = 15.8984 (1) Å | µ = 0.31 mm−1 |
β = 90.628 (1)° | T = 84 K |
V = 916.47 (2) Å3 | Plate, colourless |
Z = 2 | 0.68 × 0.40 × 0.17 mm |
Siemens SMART CCD area-detector diffractometer | 3685 independent reflections |
Radiation source: fine-focus sealed tube | 3592 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 27.1°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.789, Tmax = 0.912 | k = −9→9 |
9314 measured reflections | l = −20→20 |
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)] = 0.022 | H-atom parameters constrained |
wR(F2) = 0.058 | w = 1/[σ2(Fo2) + (0.0305P)2 + 0.1652P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3685 reflections | Δρmax = 0.33 e Å−3 |
226 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with how many Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.02 (4) |
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 | 0.51118 (4) | 0.34732 (5) | 0.68440 (2) | 0.01683 (8) | |
S2 | 0.52689 (4) | 0.73531 (5) | 0.75020 (2) | 0.01770 (8) | |
O1 | 0.40089 (14) | 0.65028 (16) | 0.80331 (7) | 0.0269 (3) | |
O2 | 0.48692 (14) | 0.90519 (15) | 0.70972 (7) | 0.0238 (2) | |
O6'' | 0.93092 (12) | 1.06997 (13) | 0.85808 (6) | 0.0151 (2) | |
O1'' | 0.78651 (11) | 1.34573 (15) | 0.87578 (6) | 0.01571 (19) | |
N3 | 0.67137 (15) | 0.60976 (19) | 0.60685 (8) | 0.0190 (3) | |
C7a | 0.62301 (18) | 0.2934 (2) | 0.59338 (9) | 0.0167 (3) | |
C7 | 0.64357 (18) | 0.1240 (2) | 0.55511 (9) | 0.0204 (3) | |
H7 | 0.5920 | 0.0204 | 0.5765 | 0.024* | |
C6 | 0.74483 (19) | 0.1174 (3) | 0.48342 (10) | 0.0244 (3) | |
H6 | 0.7627 | 0.0068 | 0.4569 | 0.029* | |
C5 | 0.8206 (2) | 0.2750 (3) | 0.45044 (10) | 0.0268 (4) | |
H5 | 0.8862 | 0.2663 | 0.4021 | 0.032* | |
C4 | 0.7999 (2) | 0.4416 (2) | 0.48796 (10) | 0.0247 (3) | |
H4 | 0.8508 | 0.5446 | 0.4657 | 0.030* | |
C3a | 0.69975 (18) | 0.4522 (2) | 0.56098 (9) | 0.0189 (3) | |
C2 | 0.57688 (18) | 0.5714 (2) | 0.67126 (9) | 0.0165 (3) | |
C1' | 0.72290 (18) | 0.7541 (2) | 0.80758 (9) | 0.0185 (3) | |
H1'A | 0.7032 | 0.8252 | 0.8579 | 0.022* | |
H1'B | 0.7587 | 0.6340 | 0.8253 | 0.022* | |
C2' | 0.86923 (17) | 0.8423 (2) | 0.75767 (9) | 0.0193 (3) | |
H2'A | 0.9769 | 0.7871 | 0.7747 | 0.023* | |
H2'B | 0.8518 | 0.8176 | 0.6983 | 0.023* | |
C7'' | 0.88128 (17) | 1.0461 (2) | 0.77062 (9) | 0.0157 (3) | |
H7'' | 0.7682 | 1.1004 | 0.7612 | 0.019* | |
C8'' | 1.01000 (18) | 1.1358 (2) | 0.71238 (9) | 0.0191 (3) | |
H8''A | 0.9710 | 1.1243 | 0.6545 | 0.023* | |
H8''B | 1.1198 | 1.0753 | 0.7177 | 0.023* | |
C9'' | 1.03014 (17) | 1.3366 (2) | 0.73481 (9) | 0.0184 (3) | |
H9''A | 0.9239 | 1.4004 | 0.7232 | 0.022* | |
H9''B | 1.1193 | 1.3904 | 0.7009 | 0.022* | |
C10'' | 1.07708 (16) | 1.3540 (2) | 0.82866 (8) | 0.0178 (3) | |
H10A | 1.1902 | 1.3035 | 0.8385 | 0.021* | |
H10B | 1.0803 | 1.4811 | 0.8441 | 0.021* | |
C5'' | 0.94813 (16) | 1.25546 (19) | 0.88352 (8) | 0.0140 (3) | |
C2'' | 0.69744 (16) | 1.3459 (2) | 0.95576 (8) | 0.0169 (3) | |
H2'' | 0.6918 | 1.4707 | 0.9767 | 0.020* | |
C3'' | 0.80902 (17) | 1.2338 (2) | 1.01610 (8) | 0.0184 (3) | |
H3''A | 0.7722 | 1.1083 | 1.0174 | 0.022* | |
H3''B | 0.8067 | 1.2830 | 1.0727 | 0.022* | |
C4'' | 0.98782 (16) | 1.2517 (2) | 0.97779 (8) | 0.0161 (3) | |
H4''A | 1.0437 | 1.3626 | 0.9960 | 0.019* | |
H4''B | 1.0596 | 1.1491 | 0.9926 | 0.019* | |
C11'' | 0.51628 (18) | 1.2760 (2) | 0.94228 (10) | 0.0248 (3) | |
H11A | 0.4565 | 1.3539 | 0.9035 | 0.037* | |
H11B | 0.4576 | 1.2746 | 0.9950 | 0.037* | |
H11C | 0.5203 | 1.1554 | 0.9197 | 0.037* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01558 (15) | 0.01636 (17) | 0.01859 (16) | −0.00168 (13) | 0.00247 (12) | 0.00063 (15) |
S2 | 0.01720 (15) | 0.01532 (17) | 0.02066 (17) | −0.00087 (14) | 0.00457 (12) | −0.00010 (14) |
O1 | 0.0272 (6) | 0.0220 (6) | 0.0317 (6) | −0.0040 (5) | 0.0142 (4) | −0.0013 (5) |
O2 | 0.0203 (5) | 0.0200 (6) | 0.0312 (6) | 0.0019 (4) | 0.0004 (4) | 0.0040 (5) |
O6'' | 0.0166 (5) | 0.0123 (5) | 0.0165 (5) | 0.0007 (4) | −0.0012 (4) | −0.0003 (4) |
O1'' | 0.0129 (4) | 0.0161 (5) | 0.0182 (4) | 0.0032 (4) | 0.0012 (3) | 0.0024 (4) |
N3 | 0.0175 (6) | 0.0223 (7) | 0.0173 (6) | −0.0032 (5) | −0.0001 (4) | 0.0012 (5) |
C7a | 0.0119 (6) | 0.0213 (7) | 0.0169 (6) | −0.0013 (5) | −0.0022 (5) | 0.0008 (5) |
C7 | 0.0181 (6) | 0.0223 (8) | 0.0207 (7) | −0.0017 (6) | −0.0032 (5) | −0.0015 (6) |
C6 | 0.0229 (7) | 0.0280 (8) | 0.0222 (8) | 0.0003 (7) | −0.0029 (6) | −0.0081 (7) |
C5 | 0.0240 (8) | 0.0361 (10) | 0.0204 (7) | −0.0044 (6) | 0.0046 (6) | −0.0058 (7) |
C4 | 0.0233 (8) | 0.0300 (9) | 0.0210 (7) | −0.0066 (6) | 0.0051 (6) | −0.0014 (7) |
C3a | 0.0158 (7) | 0.0234 (8) | 0.0174 (7) | −0.0037 (6) | −0.0022 (5) | −0.0006 (6) |
C2 | 0.0153 (6) | 0.0151 (7) | 0.0192 (6) | −0.0022 (5) | −0.0001 (5) | 0.0009 (6) |
C1' | 0.0237 (7) | 0.0145 (7) | 0.0174 (6) | −0.0010 (6) | −0.0008 (5) | −0.0008 (6) |
C2' | 0.0176 (6) | 0.0192 (7) | 0.0211 (7) | 0.0005 (6) | −0.0011 (5) | −0.0030 (7) |
C7'' | 0.0133 (6) | 0.0172 (7) | 0.0167 (6) | 0.0009 (5) | −0.0011 (5) | −0.0011 (6) |
C8'' | 0.0158 (7) | 0.0237 (8) | 0.0179 (7) | 0.0007 (6) | 0.0018 (5) | −0.0009 (6) |
C9'' | 0.0148 (6) | 0.0202 (7) | 0.0202 (6) | −0.0011 (6) | 0.0021 (5) | 0.0040 (6) |
C10'' | 0.0139 (6) | 0.0178 (7) | 0.0218 (7) | −0.0023 (6) | 0.0007 (5) | 0.0009 (6) |
C5'' | 0.0105 (6) | 0.0124 (7) | 0.0192 (6) | 0.0007 (5) | −0.0018 (4) | −0.0009 (6) |
C2'' | 0.0156 (6) | 0.0160 (7) | 0.0190 (6) | −0.0001 (6) | 0.0020 (5) | 0.0010 (6) |
C3'' | 0.0191 (6) | 0.0190 (7) | 0.0172 (6) | 0.0027 (6) | 0.0007 (5) | 0.0009 (6) |
C4'' | 0.0161 (6) | 0.0122 (7) | 0.0201 (7) | −0.0004 (6) | −0.0024 (5) | −0.0006 (6) |
C11'' | 0.0151 (7) | 0.0297 (9) | 0.0298 (8) | −0.0036 (6) | 0.0015 (6) | 0.0048 (7) |
S1—C7a | 1.7446 (15) | C2'—H2'A | 0.9700 |
S1—C2 | 1.7446 (15) | C2'—H2'B | 0.9700 |
S2—O2 | 1.4417 (12) | C7''—C8'' | 1.525 (2) |
S2—O1 | 1.4470 (11) | C7''—H7'' | 0.9800 |
S2—C1' | 1.7794 (14) | C8''—C9'' | 1.532 (2) |
S2—C2 | 1.7891 (15) | C8''—H8''A | 0.9700 |
O6''—C5'' | 1.4330 (17) | C8''—H8''B | 0.9700 |
O6''—C7'' | 1.4502 (16) | C9''—C10'' | 1.5380 (19) |
O1''—C5'' | 1.4317 (16) | C9''—H9''A | 0.9700 |
O1''—C2'' | 1.4562 (15) | C9''—H9''B | 0.9700 |
N3—C2 | 1.3001 (19) | C10''—C5'' | 1.5242 (18) |
N3—C3a | 1.391 (2) | C10''—H10A | 0.9700 |
C7a—C7 | 1.400 (2) | C10''—H10B | 0.9700 |
C7a—C3a | 1.416 (2) | C5''—C4'' | 1.5275 (18) |
C7—C6 | 1.395 (2) | C2''—C11'' | 1.5194 (19) |
C7—H7 | 0.9300 | C2''—C3'' | 1.5317 (19) |
C6—C5 | 1.409 (2) | C2''—H2'' | 0.9800 |
C6—H6 | 0.9300 | C3''—C4'' | 1.5358 (18) |
C5—C4 | 1.376 (2) | C3''—H3''A | 0.9700 |
C5—H5 | 0.9300 | C3''—H3''B | 0.9700 |
C4—C3a | 1.409 (2) | C4''—H4''A | 0.9700 |
C4—H4 | 0.9300 | C4''—H4''B | 0.9700 |
C1'—C2' | 1.543 (2) | C11''—H11A | 0.9600 |
C1'—H1'A | 0.9700 | C11''—H11B | 0.9600 |
C1'—H1'B | 0.9700 | C11''—H11C | 0.9600 |
C2'—C7'' | 1.521 (2) | ||
C7a—S1—C2 | 88.05 (7) | C7''—C8''—C9'' | 110.18 (12) |
O2—S2—O1 | 119.47 (7) | C7''—C8''—H8''A | 109.6 |
O2—S2—C1' | 110.01 (7) | C9''—C8''—H8''A | 109.6 |
O1—S2—C1' | 108.78 (7) | C7''—C8''—H8''B | 109.6 |
O2—S2—C2 | 108.81 (7) | C9''—C8''—H8''B | 109.6 |
O1—S2—C2 | 105.75 (7) | H8''A—C8''—H8''B | 108.1 |
C1'—S2—C2 | 102.65 (7) | C8''—C9''—C10'' | 109.21 (12) |
C5''—O6''—C7'' | 114.19 (10) | C8''—C9''—H9''A | 109.8 |
C5''—O1''—C2'' | 110.79 (10) | C10''—C9''—H9''A | 109.8 |
C2—N3—C3a | 109.04 (13) | C8''—C9''—H9''B | 109.8 |
C7—C7a—C3a | 121.99 (13) | C10''—C9''—H9''B | 109.8 |
C7—C7a—S1 | 128.66 (12) | H9''A—C9''—H9''B | 108.3 |
C3a—C7a—S1 | 109.34 (11) | C5''—C10''—C9'' | 111.31 (11) |
C6—C7—C7a | 117.03 (15) | C5''—C10''—H10A | 109.4 |
C6—C7—H7 | 121.5 | C9''—C10''—H10A | 109.4 |
C7a—C7—H7 | 121.5 | C5''—C10''—H10B | 109.4 |
C7—C6—C5 | 121.32 (16) | C9''—C10''—H10B | 109.4 |
C7—C6—H6 | 119.3 | H10A—C10''—H10B | 108.0 |
C5—C6—H6 | 119.3 | O1''—C5''—O6'' | 109.88 (10) |
C4—C5—C6 | 121.59 (14) | O1''—C5''—C10'' | 108.48 (11) |
C4—C5—H5 | 119.2 | O6''—C5''—C10'' | 110.76 (11) |
C6—C5—H5 | 119.2 | O1''—C5''—C4'' | 105.20 (10) |
C5—C4—C3a | 118.41 (15) | O6''—C5''—C4'' | 106.08 (11) |
C5—C4—H4 | 120.8 | C10''—C5''—C4'' | 116.22 (11) |
C3a—C4—H4 | 120.8 | O1''—C2''—C11'' | 109.26 (11) |
N3—C3a—C4 | 124.85 (15) | O1''—C2''—C3'' | 105.79 (10) |
N3—C3a—C7a | 115.48 (13) | C11''—C2''—C3'' | 115.34 (13) |
C4—C3a—C7a | 119.66 (15) | O1''—C2''—H2'' | 108.8 |
N3—C2—S1 | 118.09 (11) | C11''—C2''—H2'' | 108.8 |
N3—C2—S2 | 122.39 (11) | C3''—C2''—H2'' | 108.8 |
S1—C2—S2 | 119.33 (8) | C2''—C3''—C4'' | 102.66 (11) |
C2'—C1'—S2 | 114.06 (10) | C2''—C3''—H3''A | 111.2 |
C2'—C1'—H1'A | 108.7 | C4''—C3''—H3''A | 111.2 |
S2—C1'—H1'A | 108.7 | C2''—C3''—H3''B | 111.2 |
C2'—C1'—H1'B | 108.7 | C4''—C3''—H3''B | 111.2 |
S2—C1'—H1'B | 108.7 | H3''A—C3''—H3''B | 109.1 |
H1'A—C1'—H1'B | 107.6 | C5''—C4''—C3'' | 102.41 (10) |
C7''—C2'—C1' | 113.11 (12) | C5''—C4''—H4''A | 111.3 |
C7''—C2'—H2'A | 109.0 | C3''—C4''—H4''A | 111.3 |
C1'—C2'—H2'A | 109.0 | C5''—C4''—H4''B | 111.3 |
C7''—C2'—H2'B | 109.0 | C3''—C4''—H4''B | 111.3 |
C1'—C2'—H2'B | 109.0 | H4''A—C4''—H4''B | 109.2 |
H2'A—C2'—H2'B | 107.8 | C2''—C11''—H11A | 109.5 |
O6''—C7''—C2' | 105.39 (11) | C2''—C11''—H11B | 109.5 |
O6''—C7''—C8'' | 110.99 (11) | H11A—C11''—H11B | 109.5 |
C2'—C7''—C8'' | 112.77 (12) | C2''—C11''—H11C | 109.5 |
O6''—C7''—H7'' | 109.2 | H11A—C11''—H11C | 109.5 |
C2'—C7''—H7'' | 109.2 | H11B—C11''—H11C | 109.5 |
C8''—C7''—H7'' | 109.2 |
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