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The structure of the title compound, C16H22N2O6S, has been determined as part of an ongoing investigation into the preparation of N-alkyl­ated amino acid precursors for alkene cross-metathesis reactions for the generation of dynamic combinatorial libraries. The overall molecular conformation is stabilized by intramolecular C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003186/tk6153sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003186/tk6153Isup2.hkl
Contains datablock I

CCDC reference: 236083

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.040
  • wR factor = 0.120
  • Data-to-parameter ratio = 10.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.50 Ratio PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.45 Ratio
Alert level C PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C14 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT368_ALERT_2_C Short C(sp2)-C(sp2) Bond C11 - C12 = 1.20 Ang.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2353 Count of symmetry unique reflns 2355 Completeness (_total/calc) 99.92% 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
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 5 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

Computing details top

Data collection: MSC/AFC7 Diffractometer Control for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2002).

(I) top
Crystal data top
C16H22N2O6SF(000) = 784
Mr = 370.43Dx = 1.288 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.7107 Å
Hall symbol: C 2yCell parameters from 25 reflections
a = 15.7515 (15) Åθ = 12.9–16.9°
b = 8.2452 (17) ŵ = 0.20 mm1
c = 15.673 (2) ÅT = 295 K
β = 110.153 (9)°Prismatic, colorless
V = 1910.9 (5) Å30.35 × 0.30 × 0.20 mm
Z = 4
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.025
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.6°
Graphite monochromatorh = 820
ω–2θ scansk = 010
2590 measured reflectionsl = 2019
2353 independent reflections3 standard reflections every 150 reflections
1634 reflections with I > 2σ(I) intensity decay: 1.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters not refined
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0613P)2 + 0.3996P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.009
2353 reflectionsΔρmax = 0.16 e Å3
226 parametersΔρmin = 0.21 e Å3
1 restraintAbsolute structure: Flack (1983); 0 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.20 (12)
Special details top

Experimental. The scan width was (1.73 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.87989 (6)0.01889 (12)0.29351 (6)0.0575 (3)
O10.6837 (4)0.3590 (5)0.2064 (3)0.128 (2)
O20.6639 (2)0.1012 (4)0.1950 (2)0.0810 (11)
O30.8531 (2)0.1087 (4)0.21093 (17)0.0704 (10)
O40.97305 (18)0.0122 (5)0.3487 (2)0.0846 (13)
O50.6828 (2)0.2526 (5)0.28698 (18)0.0779 (13)
O60.61864 (17)0.2870 (4)0.13735 (17)0.0640 (10)
N10.6944 (3)0.2207 (5)0.2375 (2)0.0711 (14)
N20.8464 (2)0.1659 (4)0.27196 (19)0.0532 (10)
C10.8260 (2)0.1102 (5)0.3656 (2)0.0525 (11)
C20.7496 (3)0.2049 (5)0.3349 (2)0.0569 (11)
C30.7186 (3)0.2917 (7)0.3941 (3)0.0779 (17)
C40.7636 (4)0.2734 (7)0.4867 (3)0.081 (2)
C50.8381 (3)0.1775 (6)0.5191 (2)0.0673 (15)
C60.8705 (3)0.0991 (6)0.4589 (2)0.0620 (14)
C70.7707 (2)0.2094 (4)0.1891 (2)0.0440 (10)
C80.6869 (2)0.2516 (5)0.2128 (2)0.0495 (12)
C90.5347 (3)0.3357 (8)0.1485 (4)0.095 (2)
C100.8832 (3)0.2895 (7)0.3431 (3)0.0768 (16)
C110.9702 (4)0.3644 (10)0.3427 (4)0.108 (3)
C120.9932 (7)0.5041 (13)0.3526 (9)0.198 (5)
C130.7977 (3)0.3415 (5)0.1363 (2)0.0564 (11)
C140.8729 (3)0.2980 (6)0.1010 (3)0.0716 (16)
C150.8455 (4)0.1675 (8)0.0293 (4)0.100 (2)
C160.9052 (5)0.4511 (11)0.0660 (4)0.130 (3)
H30.667800.361800.371700.0940*
H40.742100.328900.528400.0970*
H50.867500.164500.582700.0800*
H60.924200.036500.481600.0740*
H70.756400.115700.151500.0530*
H9A0.506800.243900.164400.1130*
H9B0.495300.380400.093100.1130*
H9C0.546800.414800.195200.1130*
H10A0.893900.240000.400600.0920*
H10B0.839500.373200.334300.0920*
H111.012800.291000.333800.1300*
H12A0.953700.584300.361500.2360*
H12B1.050600.534900.350500.2360*
H13A0.816700.433100.175000.0670*
H13B0.745800.369300.085600.0670*
H140.922100.257600.150700.0860*
H15A0.795500.204100.020900.1210*
H15B0.828900.072500.054000.1210*
H15C0.894800.143900.009600.1210*
H16A0.858900.488800.012900.1560*
H16B0.919100.532700.111500.1560*
H16C0.957800.426600.051800.1560*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0525 (5)0.0739 (7)0.0551 (5)0.0184 (5)0.0302 (4)0.0209 (5)
O10.240 (6)0.064 (2)0.076 (2)0.034 (3)0.048 (3)0.0191 (18)
O20.085 (2)0.071 (2)0.0709 (18)0.0003 (18)0.0064 (16)0.0101 (17)
O30.0922 (19)0.0728 (19)0.0653 (15)0.0298 (16)0.0516 (15)0.0157 (14)
O40.0502 (14)0.128 (3)0.0828 (18)0.023 (2)0.0323 (13)0.047 (2)
O50.082 (2)0.103 (3)0.0657 (16)0.0038 (19)0.0472 (15)0.0045 (17)
O60.0492 (14)0.0724 (19)0.0704 (16)0.0072 (14)0.0205 (12)0.0012 (15)
N10.102 (3)0.051 (2)0.0605 (19)0.016 (2)0.0283 (19)0.0058 (19)
N20.0541 (15)0.058 (2)0.0462 (15)0.0024 (15)0.0156 (13)0.0075 (14)
C10.0548 (19)0.060 (2)0.0513 (18)0.0163 (19)0.0292 (16)0.0158 (17)
C20.071 (2)0.051 (2)0.0536 (19)0.0041 (19)0.0276 (17)0.0034 (17)
C30.091 (3)0.077 (3)0.072 (3)0.018 (3)0.036 (2)0.010 (2)
C40.099 (4)0.087 (4)0.066 (3)0.007 (3)0.040 (2)0.023 (3)
C50.072 (3)0.088 (3)0.0466 (19)0.005 (2)0.0263 (18)0.013 (2)
C60.054 (2)0.081 (3)0.0540 (19)0.008 (2)0.0223 (16)0.016 (2)
C70.0485 (17)0.0445 (18)0.0422 (15)0.0033 (15)0.0198 (13)0.0026 (14)
C80.054 (2)0.047 (2)0.055 (2)0.0023 (17)0.0285 (17)0.0049 (17)
C90.053 (2)0.101 (4)0.133 (4)0.012 (3)0.036 (3)0.010 (4)
C100.082 (3)0.086 (3)0.057 (2)0.018 (3)0.017 (2)0.009 (2)
C110.081 (4)0.121 (6)0.103 (4)0.041 (4)0.007 (3)0.012 (4)
C120.162 (8)0.139 (8)0.286 (12)0.080 (7)0.069 (9)0.071 (9)
C130.062 (2)0.057 (2)0.0544 (19)0.0002 (18)0.0256 (17)0.0092 (18)
C140.064 (2)0.100 (4)0.062 (2)0.003 (2)0.0360 (19)0.016 (2)
C150.131 (4)0.117 (5)0.080 (3)0.009 (4)0.071 (3)0.006 (3)
C160.138 (5)0.150 (7)0.137 (5)0.039 (5)0.093 (5)0.016 (5)
Geometric parameters (Å, º) top
S1—O31.423 (3)C14—C161.532 (10)
S1—O41.425 (3)C3—H30.9508
S1—N21.610 (3)C4—H40.9507
S1—C11.796 (4)C5—H50.9495
O1—N11.229 (6)C6—H60.9493
O2—N11.194 (5)C7—H70.9505
O5—C81.186 (4)C9—H9A0.9506
O6—C81.328 (4)C9—H9B0.9506
O6—C91.449 (6)C9—H9C0.9494
N1—C21.479 (4)C10—H10A0.9500
N2—C71.473 (4)C10—H10B0.9506
N2—C101.474 (6)C11—H110.9489
C1—C21.375 (6)C12—H12A0.9506
C1—C61.390 (4)C12—H12B0.9505
C2—C31.387 (6)C13—H13A0.9502
C3—C41.387 (6)C13—H13B0.9511
C4—C51.360 (8)C14—H140.9499
C5—C61.379 (6)C15—H15A0.9505
C7—C81.529 (5)C15—H15B0.9495
C7—C131.515 (5)C15—H15C0.9494
C10—C111.505 (9)C16—H16A0.9502
C11—C121.201 (14)C16—H16B0.9495
C13—C141.513 (7)C16—H16C0.9507
C14—C151.508 (8)
S1···O23.286 (3)C9···H16Bviii3.0275
O1···O6i3.159 (5)C10···H13A2.7457
O1···C8i3.212 (6)C11···H13A2.9489
O1···C9i3.347 (8)C11···H142.9722
O2···C82.933 (5)C13···H10B2.9537
O2···O32.904 (5)C15···H72.7699
O2···O53.222 (5)C15···H13Bix3.0939
O2···S13.286 (3)C16···H9Ax3.0112
O2···C73.083 (5)H3···O12.6874
O3···N12.827 (6)H4···O5vi2.8045
O3···O22.904 (5)H4···C6vi2.8969
O3···C9ii3.358 (6)H5···O4iii2.6796
O4···C5iii3.279 (5)H5···O5vi2.5262
O4···C6iii3.249 (5)H6···O42.4648
O4···C113.106 (9)H6···H10A2.5728
O5···O23.222 (5)H6···O4iii2.6014
O5···C5iv3.220 (5)H6···C6iii3.0847
O5···N22.761 (5)H6···H6iii2.2552
O5···C4iv3.358 (5)H7···O22.5437
O5···C102.986 (6)H7···O32.3735
O6···O1v3.159 (5)H7···C152.7699
O1···H13Ai2.8775H7···H15B2.2290
O1···H32.6874H9A···O52.7770
O1···H9Ci2.8104H9A···C16viii3.0112
O2···H72.5437H9A···H16Bviii2.1998
O3···H15B2.7894H9C···O1v2.8104
O3···H72.3735H9C···O52.5147
O4···H5iii2.6796H10A···O42.6905
O4···H10A2.6905H10A···C13.0624
O4···H112.6071H10A···C63.0034
O4···H62.4648H10A···H62.5728
O4···H6iii2.6014H10B···O52.5238
O5···H10B2.5238H10B···C82.6935
O5···H9C2.5147H10B···C132.9537
O5···H4iv2.8045H10B···H12A2.4328
O5···H5iv2.5262H10B···H13A2.4472
O5···H9A2.7770H11···O42.6071
O6···H13B2.4999H12A···H10B2.4328
N1···O32.827 (6)H13A···O1v2.8775
N2···O52.761 (5)H13A···C102.7457
N2···H142.6771H13A···C112.9489
C4···O5vi3.358 (5)H13A···H10B2.4472
C5···O5vi3.220 (5)H13A···H16B2.3179
C5···O4iii3.279 (5)H13B···O62.4999
C6···O4iii3.249 (5)H13B···H15A2.4809
C7···O23.083 (5)H13B···C15xi3.0939
C8···O22.933 (5)H14···N22.6771
C8···O1v3.212 (6)H14···C112.9722
C9···O3vii3.358 (6)H15A···H13B2.4809
C9···O1v3.347 (8)H15A···H16A2.5345
C10···O52.986 (6)H15B···O32.7894
C11···C133.439 (7)H15B···C72.8170
C11···O43.106 (9)H15B···H72.2290
C13···C113.439 (7)H15C···H16C2.5304
C1···H10A3.0624H16A···H15A2.5345
C6···H6iii3.0847H16B···H13A2.3179
C6···H10A3.0034H16B···C9x3.0275
C6···H4iv2.8969H16B···H9Ax2.1998
C7···H15B2.8170H16C···H15C2.5304
C8···H10B2.6935H16C···H16Cxii2.4272
O3—S1—O4119.5 (2)C1—C6—H6119.43
O3—S1—N2109.19 (17)C5—C6—H6119.38
O3—S1—C1107.32 (18)N2—C7—H7107.20
O4—S1—N2106.6 (2)C8—C7—H7107.19
O4—S1—C1104.21 (17)C13—C7—H7107.27
N2—S1—C1109.70 (18)O6—C9—H9A109.54
C8—O6—C9116.5 (3)O6—C9—H9B109.45
O1—N1—O2124.8 (4)O6—C9—H9C109.53
O1—N1—C2116.3 (4)H9A—C9—H9B109.44
O2—N1—C2118.9 (4)H9A—C9—H9C109.45
S1—N2—C7121.5 (2)H9B—C9—H9C109.41
S1—N2—C10118.7 (3)N2—C10—H10A108.39
C7—N2—C10119.1 (3)N2—C10—H10B108.41
S1—C1—C2124.4 (2)C11—C10—H10A108.42
S1—C1—C6117.3 (3)C11—C10—H10B108.44
C2—C1—C6118.0 (3)H10A—C10—H10B109.42
N1—C2—C1122.9 (3)C10—C11—H11115.46
N1—C2—C3115.3 (4)C12—C11—H11115.68
C1—C2—C3121.8 (3)C11—C12—H12A120.16
C2—C3—C4118.2 (5)C11—C12—H12B119.99
C3—C4—C5121.2 (5)H12A—C12—H12B119.85
C4—C5—C6119.5 (3)C7—C13—H13A107.99
C1—C6—C5121.2 (4)C7—C13—H13B107.90
N2—C7—C8110.2 (3)C14—C13—H13A107.92
N2—C7—C13111.2 (3)C14—C13—H13B107.91
C8—C7—C13113.4 (3)H13A—C13—H13B109.44
O5—C8—O6124.8 (3)C13—C14—H14107.67
O5—C8—C7125.6 (3)C15—C14—H14107.71
O6—C8—C7109.6 (3)C16—C14—H14107.75
N2—C10—C11113.7 (4)C14—C15—H15A109.46
C10—C11—C12128.9 (8)C14—C15—H15B109.46
C7—C13—C14115.6 (4)C14—C15—H15C109.42
C13—C14—C15112.5 (4)H15A—C15—H15B109.47
C13—C14—C16109.5 (5)H15A—C15—H15C109.46
C15—C14—C16111.5 (4)H15B—C15—H15C109.54
C2—C3—H3120.81C14—C16—H16A109.51
C4—C3—H3120.95C14—C16—H16B109.52
C3—C4—H4119.50C14—C16—H16C109.42
C5—C4—H4119.28H16A—C16—H16B109.56
C4—C5—H5120.24H16A—C16—H16C109.41
C6—C5—H5120.26H16B—C16—H16C109.41
O3—S1—N2—C722.6 (3)S1—N2—C10—C1187.4 (5)
O3—S1—N2—C10166.7 (3)C7—N2—C10—C11101.7 (5)
O4—S1—N2—C7153.0 (3)S1—C1—C2—C3170.3 (4)
O4—S1—N2—C1036.3 (4)S1—C1—C2—N110.3 (6)
C1—S1—N2—C794.7 (3)S1—C1—C6—C5174.3 (4)
C1—S1—N2—C1076.0 (3)C6—C1—C2—N1177.4 (4)
O3—S1—C1—C221.9 (4)C6—C1—C2—C32.1 (7)
O3—S1—C1—C6150.5 (3)C2—C1—C6—C51.4 (7)
O4—S1—C1—C2149.6 (4)C1—C2—C3—C43.9 (8)
O4—S1—C1—C622.8 (4)N1—C2—C3—C4175.6 (5)
N2—S1—C1—C296.6 (4)C2—C3—C4—C52.3 (8)
N2—S1—C1—C691.0 (4)C3—C4—C5—C61.1 (8)
C9—O6—C8—O52.3 (7)C4—C5—C6—C13.0 (8)
C9—O6—C8—C7177.8 (4)N2—C7—C8—O51.3 (6)
O2—N1—C2—C3122.5 (5)C13—C7—C8—O655.9 (4)
O1—N1—C2—C357.6 (7)N2—C7—C13—C1462.4 (4)
O2—N1—C2—C156.9 (7)C8—C7—C13—C14172.7 (3)
O1—N1—C2—C1122.9 (6)N2—C7—C8—O6178.6 (3)
S1—N2—C7—C8106.8 (3)C13—C7—C8—O5124.2 (4)
S1—N2—C7—C13126.5 (3)N2—C10—C11—C12138.1 (10)
C10—N2—C7—C863.8 (4)C7—C13—C14—C16169.0 (4)
C10—N2—C7—C1362.9 (4)C7—C13—C14—C1566.4 (5)
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z; (iii) x+2, y, z+1; (iv) x+3/2, y1/2, z+1; (v) x, y1, z; (vi) x+3/2, y+1/2, z+1; (vii) x1/2, y1/2, z; (viii) x1/2, y+1/2, z; (ix) x+3/2, y+1/2, z; (x) x+1/2, y1/2, z; (xi) x+3/2, y1/2, z; (xii) x+2, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O5vi0.952.533.220 (5)130
C6—H6···O40.952.462.833 (5)103
C7—H7···O20.952.543.083 (5)116
C7—H7···O30.952.372.894 (5)114
C10—H10B···O50.952.522.986 (6)110
C13—H13B···O60.952.502.862 (6)103
Symmetry code: (vi) x+3/2, y+1/2, z+1.
 

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