Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802000880/na6131sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802000880/na6131Isup2.hkl |
CCDC reference: 180795
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.035
- wR factor = 0.107
- Data-to-parameter ratio = 10.3
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level B:
PLAT_030 Alert B Refined Extinction parameter within range .... 2.00 Sigma General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 26.98 From the CIF: _reflns_number_total 1695 Count of symmetry unique reflns 1697 Completeness (_total/calc) 99.88% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
0 Alert Level C = Please check
Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CELDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1993).
C13H15NO3S | Dx = 1.319 Mg m−3 |
Mr = 265.32 | Mo Kα radiation, λ = 0.71069 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 6.1961 (14) Å | θ = 9–17° |
b = 13.613 (4) Å | µ = 0.24 mm−1 |
c = 15.842 (2) Å | T = 298 K |
V = 1336.2 (6) Å3 | Block, colourless |
Z = 4 | 0.60 × 0.50 × 0.40 mm |
F(000) = 560 |
Enraf-Nonius CAD-4 diffractometer | 1245 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.005 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
ω–2θ scans | h = 0→7 |
Absorption correction: ψ scan (ABSCALC in OSCAIL; McArdle & Daly, 1999; North et al., 1986) | k = 0→17 |
Tmin = 0.869, Tmax = 0.910 | l = 0→20 |
1734 measured reflections | 3 standard reflections every 120 min |
1695 independent reflections | intensity decay: none |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.064P)2 + 0.0882P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.107 | (Δ/σ)max = 0.006 |
S = 1.04 | Δρmax = 0.22 e Å−3 |
1695 reflections | Δρmin = −0.18 e Å−3 |
165 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.004 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: (Flack, 1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.22 (14) |
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) Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 2.5128 (0.0084) x + 9.9056 (0.0148) y - 8.7638 (0.0195) z = 2.6812 (0.0241) * 0.0009 (0.0022) C8 * 0.0034 (0.0025) C9 * -0.0051 (0.0029) C10 * 0.0023 (0.0030) C11 * 0.0020 (0.0028) C12 * -0.0036 (0.0023) C13 0.0177 (0.0055) C7 - 0.5401 (0.0054) O3 - 0.6974 (0.0075) C6 - 0.4491 (0.0080) O2 - 1.1976 (0.0082) N1 Rms deviation of fitted atoms = 0.0032 - 2.5785 (0.0145) x + 11.0127 (0.0124) y - 6.5767 (0.0274) z = 4.0023 (0.0262) Angle to previous plane (with approximate e.s.d.) = 9.21 (1/4) * 0.0027 (0.0010) C1 * -0.0063 (0.0023) C2 * 0.0064 (0.0023) C3 * -0.0027 (0.0010) C4 - 0.6413 (0.0059) S1 0.1723 (0.0057) N1 - 2.0715 (0.0054) O1 - 1.2437 (0.0055) C5 0.7013 (0.0085) C6 1.1218 (0.0088) O2 0.6734 (0.0110) O3 1.2430 (0.0145) C7 1.0086 (0.0173) C8 Rms deviation of fitted atoms = 0.0049 4.2624 (0.0044) x - 6.6330 (0.0183) y + 8.5215 (0.0137) z = 1.3214 (0.0257) Angle to previous plane (with approximate e.s.d.) = 25.34 (0.23) * 0.0004 (0.0015) N1 * 0.0020 (0.0024) C6 * 0.0280 (0.0015) O2 * -0.0168 (0.0021) O3 * -0.0598 (0.0030) C7 * 0.0463 (0.0019) C8 Rms deviation of fitted atoms = 0.0337 |
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 | 0.08303 (14) | 0.76417 (5) | 0.73601 (5) | 0.0617 (2) | |
N1 | 0.0832 (4) | 0.87138 (14) | 0.79177 (13) | 0.0548 (5) | |
O2 | 0.2626 (4) | 1.01446 (14) | 0.81665 (14) | 0.0703 (6) | |
O3 | 0.3397 (4) | 0.92319 (13) | 0.70174 (13) | 0.0672 (6) | |
O1 | 0.1581 (4) | 0.68484 (14) | 0.79119 (17) | 0.0784 (7) | |
C1 | −0.2064 (6) | 0.7522 (2) | 0.7315 (2) | 0.0773 (10) | |
H1A | −0.2614 | 0.7964 | 0.6885 | 0.100* | |
H1B | −0.2419 | 0.6857 | 0.7144 | 0.100* | |
C2 | −0.3174 (6) | 0.7738 (3) | 0.8126 (3) | 0.0840 (11) | |
H2 | −0.4525 | 0.7457 | 0.8209 | 0.109* | |
C3 | −0.2422 (6) | 0.8283 (2) | 0.8725 (3) | 0.0776 (10) | |
H3 | −0.3306 | 0.8371 | 0.9193 | 0.101* | |
C4 | −0.0279 (5) | 0.8788 (2) | 0.87440 (18) | 0.0618 (8) | |
H4 | −0.0553 | 0.9487 | 0.8848 | 0.080* | |
C5 | 0.1115 (7) | 0.8417 (3) | 0.9463 (2) | 0.0845 (11) | |
H5A | 0.1418 | 0.7732 | 0.9380 | 0.118* | |
H5B | 0.0365 | 0.8505 | 0.9988 | 0.118* | |
H5C | 0.2444 | 0.8779 | 0.9475 | 0.118* | |
C6 | 0.2329 (5) | 0.94327 (18) | 0.77302 (17) | 0.0544 (7) | |
C7 | 0.4952 (6) | 0.9954 (2) | 0.6752 (2) | 0.0796 (11) | |
H7A | 0.5975 | 1.0082 | 0.7202 | 0.104* | |
H7B | 0.4230 | 1.0565 | 0.6612 | 0.104* | |
C8 | 0.6100 (5) | 0.9557 (2) | 0.59927 (19) | 0.0609 (7) | |
C9 | 0.5167 (6) | 0.8866 (2) | 0.54767 (19) | 0.0717 (9) | |
H9 | 0.3792 | 0.8633 | 0.5599 | 0.093* | |
C10 | 0.6256 (8) | 0.8516 (3) | 0.4778 (2) | 0.0929 (13) | |
H10 | 0.5617 | 0.8042 | 0.4438 | 0.121* | |
C11 | 0.8267 (9) | 0.8862 (3) | 0.4584 (3) | 0.0990 (13) | |
H11 | 0.8985 | 0.8629 | 0.4109 | 0.129* | |
C12 | 0.9223 (7) | 0.9551 (3) | 0.5090 (3) | 0.0955 (13) | |
H12 | 1.0592 | 0.9786 | 0.4959 | 0.124* | |
C13 | 0.8148 (6) | 0.9899 (2) | 0.5798 (2) | 0.0785 (10) | |
H13 | 0.8804 | 1.0364 | 0.6143 | 0.102* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0719 (4) | 0.0461 (3) | 0.0670 (4) | −0.0085 (4) | 0.0011 (4) | −0.0093 (3) |
N1 | 0.0647 (13) | 0.0431 (10) | 0.0564 (11) | −0.0095 (12) | 0.0069 (13) | −0.0045 (9) |
O2 | 0.0954 (16) | 0.0457 (10) | 0.0697 (13) | −0.0158 (11) | 0.0131 (13) | −0.0106 (9) |
O3 | 0.0882 (14) | 0.0519 (10) | 0.0617 (11) | −0.0213 (11) | 0.0171 (11) | −0.0058 (9) |
O1 | 0.0716 (14) | 0.0483 (10) | 0.1153 (18) | 0.0117 (10) | −0.0143 (15) | −0.0034 (12) |
C1 | 0.081 (2) | 0.0485 (16) | 0.103 (2) | −0.0065 (15) | −0.038 (2) | 0.0067 (18) |
C2 | 0.0530 (17) | 0.0675 (19) | 0.132 (3) | −0.0009 (17) | −0.005 (2) | 0.015 (2) |
C3 | 0.064 (2) | 0.0659 (18) | 0.103 (3) | −0.0031 (17) | 0.023 (2) | 0.001 (2) |
C4 | 0.068 (2) | 0.0519 (14) | 0.0657 (17) | −0.0012 (14) | 0.0152 (15) | −0.0060 (14) |
C5 | 0.097 (3) | 0.097 (2) | 0.0599 (17) | −0.007 (2) | −0.001 (2) | −0.0024 (18) |
C6 | 0.0654 (16) | 0.0427 (12) | 0.0551 (15) | −0.0053 (12) | −0.0006 (15) | 0.0018 (12) |
C7 | 0.104 (3) | 0.0561 (17) | 0.078 (2) | −0.0282 (17) | 0.0274 (19) | −0.0034 (16) |
C8 | 0.073 (2) | 0.0476 (13) | 0.0621 (16) | −0.0037 (15) | 0.0055 (16) | 0.0111 (13) |
C9 | 0.076 (2) | 0.077 (2) | 0.0620 (18) | −0.0027 (18) | 0.0031 (18) | 0.0033 (17) |
C10 | 0.117 (4) | 0.093 (3) | 0.068 (2) | 0.001 (3) | 0.013 (2) | −0.010 (2) |
C11 | 0.114 (4) | 0.082 (2) | 0.101 (3) | 0.020 (3) | 0.039 (3) | 0.014 (2) |
C12 | 0.078 (2) | 0.078 (2) | 0.130 (3) | 0.005 (2) | 0.036 (3) | 0.028 (3) |
C13 | 0.079 (2) | 0.0601 (18) | 0.096 (3) | −0.0075 (18) | 0.007 (2) | 0.0159 (18) |
S1—O1 | 1.465 (2) | C5—H5A | 0.9600 |
S1—N1 | 1.706 (2) | C5—H5B | 0.9600 |
S1—C1 | 1.802 (4) | C5—H5C | 0.9600 |
N1—C6 | 1.381 (3) | C7—C8 | 1.499 (4) |
N1—C4 | 1.482 (4) | C7—H7A | 0.9700 |
O2—C6 | 1.204 (3) | C7—H7B | 0.9700 |
O3—C6 | 1.337 (3) | C8—C9 | 1.373 (4) |
O3—C7 | 1.439 (3) | C8—C13 | 1.386 (5) |
C1—C2 | 1.487 (6) | C9—C10 | 1.381 (5) |
C1—H1A | 0.9700 | C9—H9 | 0.9300 |
C1—H1B | 0.9700 | C10—C11 | 1.367 (6) |
C2—C3 | 1.292 (5) | C10—H10 | 0.9300 |
C2—H2 | 0.9300 | C11—C12 | 1.369 (6) |
C3—C4 | 1.495 (5) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.388 (5) |
C4—C5 | 1.516 (5) | C12—H12 | 0.9300 |
C4—H4 | 0.9800 | C13—H13 | 0.9300 |
O1—S1—N1 | 108.75 (13) | H5A—C5—H5C | 109.5 |
O1—S1—C1 | 105.84 (15) | H5B—C5—H5C | 109.5 |
N1—S1—C1 | 95.65 (14) | O2—C6—O3 | 125.0 (3) |
C6—N1—C4 | 117.0 (2) | O2—C6—N1 | 123.3 (3) |
C6—N1—S1 | 119.69 (19) | O3—C6—N1 | 111.7 (2) |
C4—N1—S1 | 121.02 (18) | O3—C7—C8 | 107.8 (2) |
C6—O3—C7 | 116.0 (2) | O3—C7—H7A | 110.1 |
C2—C1—S1 | 114.1 (2) | C8—C7—H7A | 110.1 |
C2—C1—H1A | 108.7 | O3—C7—H7B | 110.1 |
S1—C1—H1A | 108.7 | C8—C7—H7B | 110.1 |
C2—C1—H1B | 108.7 | H7A—C7—H7B | 108.5 |
S1—C1—H1B | 108.7 | C9—C8—C13 | 118.9 (3) |
H1A—C1—H1B | 107.6 | C9—C8—C7 | 121.7 (3) |
C3—C2—C1 | 125.6 (3) | C13—C8—C7 | 119.5 (3) |
C3—C2—H2 | 117.2 | C8—C9—C10 | 120.5 (4) |
C1—C2—H2 | 117.2 | C8—C9—H9 | 119.7 |
C2—C3—C4 | 126.8 (3) | C10—C9—H9 | 119.7 |
C2—C3—H3 | 116.6 | C11—C10—C9 | 120.4 (4) |
C4—C3—H3 | 116.6 | C11—C10—H10 | 119.8 |
N1—C4—C3 | 111.3 (3) | C9—C10—H10 | 119.8 |
N1—C4—C5 | 112.1 (3) | C12—C11—C10 | 119.9 (4) |
C3—C4—C5 | 111.6 (3) | C12—C11—H11 | 120.0 |
N1—C4—H4 | 107.2 | C10—C11—H11 | 120.0 |
C3—C4—H4 | 107.2 | C11—C12—C13 | 120.0 (4) |
C5—C4—H4 | 107.2 | C11—C12—H12 | 120.0 |
C4—C5—H5A | 109.5 | C13—C12—H12 | 120.0 |
C4—C5—H5B | 109.5 | C8—C13—C12 | 120.3 (4) |
H5A—C5—H5B | 109.5 | C8—C13—H13 | 119.8 |
C4—C5—H5C | 109.5 | C12—C13—H13 | 119.8 |
O1—S1—N1—C6 | 109.8 (2) | C4—N1—C6—O2 | −6.5 (4) |
C1—S1—N1—C6 | −141.4 (2) | S1—N1—C6—O2 | −169.4 (2) |
O1—S1—N1—C4 | −52.4 (3) | C4—N1—C6—O3 | 173.0 (2) |
C1—S1—N1—C4 | 56.4 (3) | S1—N1—C6—O3 | 10.1 (3) |
O1—S1—C1—C2 | 67.6 (3) | C6—O3—C7—C8 | 175.1 (3) |
N1—S1—C1—C2 | −43.7 (3) | O3—C7—C8—C9 | 24.8 (4) |
S1—C1—C2—C3 | 24.2 (5) | O3—C7—C8—C13 | −155.9 (3) |
C1—C2—C3—C4 | −1.7 (6) | C13—C8—C9—C10 | 0.3 (5) |
C6—N1—C4—C3 | 155.1 (3) | C7—C8—C9—C10 | 179.7 (3) |
S1—N1—C4—C3 | −42.2 (3) | C8—C9—C10—C11 | −0.9 (6) |
C6—N1—C4—C5 | −79.2 (3) | C9—C10—C11—C12 | 0.8 (6) |
S1—N1—C4—C5 | 83.5 (3) | C10—C11—C12—C13 | −0.1 (6) |
C2—C3—C4—N1 | 8.4 (5) | C9—C8—C13—C12 | 0.4 (4) |
C2—C3—C4—C5 | −117.6 (4) | C7—C8—C13—C12 | −179.0 (3) |
C7—O3—C6—O2 | −2.5 (4) | C11—C12—C13—C8 | −0.5 (5) |
C7—O3—C6—N1 | 178.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O2i | 0.97 | 2.39 | 3.345 (4) | 169 |
C9—H9···O3 | 0.93 | 2.40 | 2.722 (4) | 100 |
C5—H5A···O1 | 0.96 | 2.62 | 3.269 (4) | 125 |
C2—H2···O1ii | 0.93 | 2.59 | 3.485 (5) | 161 |
C4—H4···O2 | 0.98 | 2.42 | 2.736 (4) | 98 |
C7—H7A···O2 | 0.97 | 2.58 | 2.677 (4) | 85 |
C13—H13···O1iii | 0.93 | 2.53 | 3.354 (4) | 148 |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) −x+1, y+1/2, −z+3/2. |
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