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The structure of the title compound, C10H12N2O6S, has been determined as part of an ongoing investigation into the preparation of substituted amino acids suitable for the generation of combinatorial libraries. The molecular conformation is stabilized by intra- and intermolecular N—H...O and C—H...O hydrogen-bonding interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805014315/nc6028sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805014315/nc6028Isup2.hkl
Contains datablock I

CCDC reference: 274593

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.036
  • wR factor = 0.105
  • Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 27.49 From the CIF: _reflns_number_total 1608 Count of symmetry unique reflns 1552 Completeness (_total/calc) 103.61% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 56 Fraction of Friedel pairs measured 0.036 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 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: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows aaand PLATON (Spek, 2003).

N-(2-nitrobenzenesulfonyl)-L-alanine methyl ester top
Crystal data top
C10H12N2O6SF(000) = 300
Mr = 288.29Dx = 1.476 Mg m3
Monoclinic, P21Melting point: 359 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.7107 Å
a = 8.845 (3) ÅCell parameters from 25 reflections
b = 13.335 (5) Åθ = 12.8–17.0°
c = 5.5203 (10) ŵ = 0.27 mm1
β = 95.10 (2)°T = 295 K
V = 648.5 (3) Å3Prismatic, colorless
Z = 20.40 × 0.20 × 0.15 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.033
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.8°
Graphite monochromatorh = 011
ω–2θ scansk = 617
1708 measured reflectionsl = 77
1608 independent reflections3 standard reflections every 150 reflections
1252 reflections with I > 2σ(I) intensity decay: 1.8%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0631P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max = 0.018
S = 1.02Δρmax = 0.20 e Å3
1608 reflectionsΔρmin = 0.21 e Å3
173 parametersExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
1 restraintExtinction coefficient: 0.041 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.24 (12)
Special details top

Experimental. The scan width was (1.47 + 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 su'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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.21572 (11)0.79482 (7)0.30884 (13)0.0469 (2)
O10.0574 (4)0.8623 (3)0.1697 (5)0.0753 (13)
O20.1436 (4)0.9414 (4)0.0973 (8)0.120 (2)
O30.0778 (4)0.7430 (2)0.2378 (5)0.0658 (10)
O40.2966 (4)0.77223 (18)0.5389 (4)0.0612 (9)
O50.4676 (3)0.9698 (2)0.0264 (5)0.0607 (9)
O60.6211 (4)0.9337 (2)0.3575 (5)0.0717 (11)
N10.3333 (4)0.77466 (19)0.1071 (4)0.0476 (10)
N20.0115 (4)0.9217 (3)0.0549 (6)0.0677 (14)
C10.1751 (4)0.9252 (2)0.3148 (6)0.0415 (9)
C20.0725 (4)0.9752 (3)0.1511 (7)0.0509 (11)
C30.0444 (6)1.0766 (4)0.1701 (10)0.0721 (17)
C40.1188 (6)1.1298 (3)0.3554 (11)0.077 (2)
C50.2194 (6)1.0833 (3)0.5191 (9)0.0702 (16)
C60.2493 (5)0.9810 (3)0.5016 (6)0.0519 (10)
C70.4949 (4)0.7982 (3)0.1611 (5)0.0480 (10)
C80.5245 (4)0.9109 (3)0.1690 (6)0.0478 (10)
C90.6588 (7)1.0394 (4)0.3886 (11)0.0861 (19)
C100.5870 (5)0.7512 (3)0.0331 (8)0.0633 (14)
H10.301700.796000.034500.0540*
H30.027801.107500.054700.0830*
H40.101501.198900.369600.0930*
H50.274601.120200.646400.0830*
H60.317600.948900.618300.0610*
H70.528300.769700.313700.0560*
H9A0.763401.044000.446500.1040*
H9B0.643001.071000.234900.1040*
H9C0.598001.068000.500100.1040*
H10A0.692100.755900.017000.0760*
H10B0.560500.681300.050600.0760*
H10C0.564800.783600.183400.0760*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0753 (6)0.0325 (3)0.0333 (3)0.0029 (4)0.0076 (3)0.0025 (4)
O10.082 (2)0.097 (3)0.0467 (14)0.0142 (19)0.0042 (14)0.0071 (16)
O20.063 (2)0.169 (5)0.122 (3)0.012 (3)0.029 (2)0.006 (3)
O30.085 (2)0.0530 (16)0.0613 (17)0.0254 (15)0.0169 (15)0.0053 (13)
O40.103 (2)0.0473 (17)0.0337 (11)0.0168 (13)0.0080 (12)0.0085 (9)
O50.0751 (18)0.0464 (14)0.0590 (15)0.0008 (13)0.0032 (13)0.0077 (12)
O60.087 (2)0.0545 (16)0.0685 (19)0.0015 (16)0.0218 (16)0.0103 (14)
N10.0699 (19)0.0407 (19)0.0318 (12)0.0033 (13)0.0018 (13)0.0036 (10)
N20.061 (2)0.084 (3)0.056 (2)0.007 (2)0.0058 (17)0.017 (2)
C10.0543 (18)0.0311 (14)0.0407 (15)0.0002 (14)0.0128 (14)0.0041 (13)
C20.0499 (19)0.054 (2)0.0505 (18)0.0023 (16)0.0135 (15)0.0097 (16)
C30.068 (3)0.066 (3)0.086 (3)0.021 (2)0.028 (2)0.029 (3)
C40.096 (4)0.041 (2)0.099 (4)0.006 (2)0.044 (3)0.001 (2)
C50.096 (3)0.049 (2)0.070 (3)0.015 (2)0.032 (3)0.019 (2)
C60.073 (2)0.0421 (17)0.0410 (17)0.0044 (17)0.0077 (16)0.0047 (15)
C70.064 (2)0.0407 (15)0.0377 (14)0.010 (2)0.0042 (13)0.0003 (18)
C80.0551 (19)0.0442 (18)0.0436 (17)0.0074 (16)0.0019 (14)0.0041 (15)
C90.090 (3)0.057 (3)0.106 (4)0.016 (3)0.020 (3)0.020 (3)
C100.076 (3)0.056 (2)0.059 (2)0.012 (2)0.012 (2)0.0119 (19)
Geometric parameters (Å, º) top
S1—O31.426 (3)C4—C51.360 (7)
S1—O41.433 (3)C5—C61.395 (6)
S1—N11.613 (3)C7—C81.525 (6)
S1—C11.776 (3)C7—C101.537 (5)
O1—N21.212 (5)C3—H30.9500
O2—N21.200 (5)C4—H40.9400
O5—C81.191 (5)C5—H50.9600
O6—C81.322 (5)C6—H60.9500
O6—C91.455 (6)C7—H70.9500
N1—C71.468 (5)C9—H9A0.9500
N2—C21.485 (5)C9—H9B0.9500
N1—H10.8600C9—H9C0.9300
C1—C21.393 (5)C10—H10A0.9500
C1—C61.388 (5)C10—H10B0.9600
C2—C31.381 (7)C10—H10C0.9400
C3—C41.365 (8)
S1···O13.015 (3)N2···O32.947 (5)
S1···O1i3.431 (3)C1···O1i3.227 (5)
O1···S1ii3.431 (3)C1···O53.212 (5)
O1···S13.015 (3)C1···C83.268 (5)
O1···O32.748 (4)C3···O3viii3.276 (6)
O1···O4ii3.019 (5)C4···O3ix3.323 (6)
O1···N12.999 (5)C6···O1i3.038 (5)
O1···C1ii3.227 (5)C6···C83.311 (6)
O1···C6ii3.038 (5)C6···O53.396 (5)
O3···C3iii3.276 (6)C6···O5i3.339 (5)
O3···C4iv3.323 (6)C8···C13.268 (5)
O3···O12.748 (4)C8···C63.311 (6)
O3···N22.947 (5)C9···O4x3.151 (6)
O4···O1i3.019 (5)C10···O4ii3.344 (5)
O4···C9v3.151 (6)C3···H9Axi3.0600
O4···C10i3.344 (5)C10···H5v2.9400
O4···N1i3.125 (3)H1···O12.3900
O5···C63.396 (5)H1···O4ii2.3700
O5···C6ii3.339 (5)H1···O52.7500
O5···C13.212 (5)H1···H10C2.5400
O5···N12.911 (4)H3···O22.5500
O1···H4iii2.7700H3···O3viii2.4400
O1···H12.3900H4···O1viii2.7700
O1···H6ii2.9100H4···O3ix2.8600
O2···H9Avi2.9200H5···C10x2.9400
O2···H32.5500H5···H10Ax2.5900
O3···H4iv2.8600H6···O1i2.9100
O3···H3iii2.4400H6···O42.4000
O4···H9Cv2.8900H6···O5i2.5300
O4···H10Ci2.7100H7···O42.4900
O4···H1i2.3700H9A···O2xii2.9200
O4···H62.4000H9A···C3xiii3.0600
O4···H72.4900H9B···O52.2900
O5···H12.7500H9B···H10Bvii2.4700
O5···H6ii2.5300H9C···O4x2.8900
O5···H9B2.2900H10A···H5v2.5900
O5···H10C2.9000H10B···O5xiv2.8400
O5···H10Bvii2.8400H10B···H9Bxiv2.4700
N1···O12.999 (5)H10C···O4ii2.7100
N1···O4ii3.125 (3)H10C···O52.9000
N1···O52.911 (4)H10C···H12.5400
O3—S1—O4119.29 (18)O6—C8—C7110.3 (3)
O3—S1—N1108.52 (17)O5—C8—O6125.0 (4)
O3—S1—C1108.05 (17)O5—C8—C7124.7 (3)
O4—S1—N1105.97 (18)C2—C3—H3119.00
O4—S1—C1105.97 (15)C4—C3—H3122.00
N1—S1—C1108.66 (15)C3—C4—H4120.00
C8—O6—C9116.2 (4)C5—C4—H4120.00
S1—N1—C7120.02 (19)C4—C5—H5121.00
O1—N2—O2124.6 (4)C6—C5—H5118.00
O1—N2—C2118.3 (3)C1—C6—H6120.00
O2—N2—C2117.2 (4)C5—C6—H6121.00
S1—N1—H1113.00N1—C7—H7108.00
C7—N1—H1110.00C8—C7—H7109.00
S1—C1—C2125.3 (3)C10—C7—H7108.00
C2—C1—C6117.6 (3)O6—C9—H9A108.00
S1—C1—C6117.1 (3)O6—C9—H9B108.00
N2—C2—C3116.6 (4)O6—C9—H9C110.00
C1—C2—C3122.1 (4)H9A—C9—H9B109.00
N2—C2—C1121.3 (3)H9A—C9—H9C111.00
C2—C3—C4119.2 (5)H9B—C9—H9C111.00
C3—C4—C5120.3 (4)C7—C10—H10A110.00
C4—C5—C6121.1 (4)C7—C10—H10B109.00
C1—C6—C5119.7 (4)C7—C10—H10C110.00
N1—C7—C10109.8 (3)H10A—C10—H10B108.00
C8—C7—C10108.8 (3)H10A—C10—H10C110.00
N1—C7—C8112.2 (3)H10B—C10—H10C109.00
O3—S1—N1—C7165.3 (3)O2—N2—C2—C1137.6 (4)
O4—S1—N1—C736.1 (3)C6—C1—C2—N2179.7 (3)
C1—S1—N1—C777.5 (3)C6—C1—C2—C30.3 (6)
O3—S1—C1—C237.3 (4)S1—C1—C6—C5178.5 (3)
O3—S1—C1—C6141.1 (3)C2—C1—C6—C50.0 (6)
O4—S1—C1—C2166.2 (3)S1—C1—C2—N21.9 (5)
O4—S1—C1—C612.2 (3)S1—C1—C2—C3178.6 (3)
N1—S1—C1—C280.3 (3)N2—C2—C3—C4179.8 (4)
N1—S1—C1—C6101.3 (3)C1—C2—C3—C40.3 (7)
C9—O6—C8—O50.0 (6)C2—C3—C4—C50.0 (8)
C9—O6—C8—C7179.5 (4)C3—C4—C5—C60.2 (8)
S1—N1—C7—C10167.4 (2)C4—C5—C6—C10.2 (7)
S1—N1—C7—C871.6 (3)N1—C7—C8—O543.2 (4)
O2—N2—C2—C342.9 (6)N1—C7—C8—O6136.3 (3)
O1—N2—C2—C143.1 (5)C10—C7—C8—O578.4 (4)
O1—N2—C2—C3136.4 (4)C10—C7—C8—O6102.1 (3)
Symmetry codes: (i) x, y, z+1; (ii) x, y, z1; (iii) x, y1/2, z; (iv) x, y1/2, z+1; (v) x+1, y1/2, z+1; (vi) x1, y, z1; (vii) x+1, y+1/2, z; (viii) x, y+1/2, z; (ix) x, y+1/2, z+1; (x) x+1, y+1/2, z+1; (xi) x1, y, z; (xii) x+1, y, z+1; (xiii) x+1, y, z; (xiv) x+1, y1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.862.392.999 (5)128
N1—H1···O4ii0.862.373.125 (3)147
C3—H3···O3viii0.952.443.276 (6)146
C6—H6···O40.952.402.820 (5)107
C6—H6···O5i0.952.533.339 (5)144
C7—H7···O40.952.492.863 (4)103
C9—H9B···O50.952.292.668 (7)103
Symmetry codes: (i) x, y, z+1; (ii) x, y, z1; (viii) x, y+1/2, z.
 

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