The structure of the title compound, C
10H
12N
2O
6S, 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
CCDC reference: 274593
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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
C10H12N2O6S | F(000) = 300 |
Mr = 288.29 | Dx = 1.476 Mg m−3 |
Monoclinic, P21 | Melting point: 359 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.7107 Å |
a = 8.845 (3) Å | Cell parameters from 25 reflections |
b = 13.335 (5) Å | θ = 12.8–17.0° |
c = 5.5203 (10) Å | µ = 0.27 mm−1 |
β = 95.10 (2)° | T = 295 K |
V = 648.5 (3) Å3 | Prismatic, colorless |
Z = 2 | 0.40 × 0.20 × 0.15 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.033 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 2.8° |
Graphite monochromator | h = 0→11 |
ω–2θ scans | k = −6→17 |
1708 measured reflections | l = −7→7 |
1608 independent reflections | 3 standard reflections every 150 reflections |
1252 reflections with I > 2σ(I) | intensity decay: 1.8% |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.02 | Δρmax = 0.20 e Å−3 |
1608 reflections | Δρmin = −0.21 e Å−3 |
173 parameters | Extinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
1 restraint | Extinction coefficient: 0.041 (7) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.21572 (11) | 0.79482 (7) | 0.30884 (13) | 0.0469 (2) | |
O1 | 0.0574 (4) | 0.8623 (3) | −0.1697 (5) | 0.0753 (13) | |
O2 | −0.1436 (4) | 0.9414 (4) | −0.0973 (8) | 0.120 (2) | |
O3 | 0.0778 (4) | 0.7430 (2) | 0.2378 (5) | 0.0658 (10) | |
O4 | 0.2966 (4) | 0.77223 (18) | 0.5389 (4) | 0.0612 (9) | |
O5 | 0.4676 (3) | 0.9698 (2) | 0.0264 (5) | 0.0607 (9) | |
O6 | 0.6211 (4) | 0.9337 (2) | 0.3575 (5) | 0.0717 (11) | |
N1 | 0.3333 (4) | 0.77466 (19) | 0.1071 (4) | 0.0476 (10) | |
N2 | −0.0115 (4) | 0.9217 (3) | −0.0549 (6) | 0.0677 (14) | |
C1 | 0.1751 (4) | 0.9252 (2) | 0.3148 (6) | 0.0415 (9) | |
C2 | 0.0725 (4) | 0.9752 (3) | 0.1511 (7) | 0.0509 (11) | |
C3 | 0.0444 (6) | 1.0766 (4) | 0.1701 (10) | 0.0721 (17) | |
C4 | 0.1188 (6) | 1.1298 (3) | 0.3554 (11) | 0.077 (2) | |
C5 | 0.2194 (6) | 1.0833 (3) | 0.5191 (9) | 0.0702 (16) | |
C6 | 0.2493 (5) | 0.9810 (3) | 0.5016 (6) | 0.0519 (10) | |
C7 | 0.4949 (4) | 0.7982 (3) | 0.1611 (5) | 0.0480 (10) | |
C8 | 0.5245 (4) | 0.9109 (3) | 0.1690 (6) | 0.0478 (10) | |
C9 | 0.6588 (7) | 1.0394 (4) | 0.3886 (11) | 0.0861 (19) | |
C10 | 0.5870 (5) | 0.7512 (3) | −0.0331 (8) | 0.0633 (14) | |
H1 | 0.30170 | 0.79600 | −0.03450 | 0.0540* | |
H3 | −0.02780 | 1.10750 | 0.05470 | 0.0830* | |
H4 | 0.10150 | 1.19890 | 0.36960 | 0.0930* | |
H5 | 0.27460 | 1.12020 | 0.64640 | 0.0830* | |
H6 | 0.31760 | 0.94890 | 0.61830 | 0.0610* | |
H7 | 0.52830 | 0.76970 | 0.31370 | 0.0560* | |
H9A | 0.76340 | 1.04400 | 0.44650 | 0.1040* | |
H9B | 0.64300 | 1.07100 | 0.23490 | 0.1040* | |
H9C | 0.59800 | 1.06800 | 0.50010 | 0.1040* | |
H10A | 0.69210 | 0.75590 | 0.01700 | 0.0760* | |
H10B | 0.56050 | 0.68130 | −0.05060 | 0.0760* | |
H10C | 0.56480 | 0.78360 | −0.18340 | 0.0760* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0753 (6) | 0.0325 (3) | 0.0333 (3) | −0.0029 (4) | 0.0076 (3) | 0.0025 (4) |
O1 | 0.082 (2) | 0.097 (3) | 0.0467 (14) | −0.0142 (19) | 0.0042 (14) | −0.0071 (16) |
O2 | 0.063 (2) | 0.169 (5) | 0.122 (3) | 0.012 (3) | −0.029 (2) | 0.006 (3) |
O3 | 0.085 (2) | 0.0530 (16) | 0.0613 (17) | −0.0254 (15) | 0.0169 (15) | −0.0053 (13) |
O4 | 0.103 (2) | 0.0473 (17) | 0.0337 (11) | 0.0168 (13) | 0.0080 (12) | 0.0085 (9) |
O5 | 0.0751 (18) | 0.0464 (14) | 0.0590 (15) | −0.0008 (13) | −0.0032 (13) | 0.0077 (12) |
O6 | 0.087 (2) | 0.0545 (16) | 0.0685 (19) | 0.0015 (16) | −0.0218 (16) | −0.0103 (14) |
N1 | 0.0699 (19) | 0.0407 (19) | 0.0318 (12) | 0.0033 (13) | 0.0018 (13) | −0.0036 (10) |
N2 | 0.061 (2) | 0.084 (3) | 0.056 (2) | −0.007 (2) | −0.0058 (17) | 0.017 (2) |
C1 | 0.0543 (18) | 0.0311 (14) | 0.0407 (15) | 0.0002 (14) | 0.0128 (14) | 0.0041 (13) |
C2 | 0.0499 (19) | 0.054 (2) | 0.0505 (18) | 0.0023 (16) | 0.0135 (15) | 0.0097 (16) |
C3 | 0.068 (3) | 0.066 (3) | 0.086 (3) | 0.021 (2) | 0.028 (2) | 0.029 (3) |
C4 | 0.096 (4) | 0.041 (2) | 0.099 (4) | 0.006 (2) | 0.044 (3) | 0.001 (2) |
C5 | 0.096 (3) | 0.049 (2) | 0.070 (3) | −0.015 (2) | 0.032 (3) | −0.019 (2) |
C6 | 0.073 (2) | 0.0421 (17) | 0.0410 (17) | −0.0044 (17) | 0.0077 (16) | −0.0047 (15) |
C7 | 0.064 (2) | 0.0407 (15) | 0.0377 (14) | 0.010 (2) | −0.0042 (13) | 0.0003 (18) |
C8 | 0.0551 (19) | 0.0442 (18) | 0.0436 (17) | 0.0074 (16) | 0.0019 (14) | −0.0041 (15) |
C9 | 0.090 (3) | 0.057 (3) | 0.106 (4) | −0.016 (3) | −0.020 (3) | −0.020 (3) |
C10 | 0.076 (3) | 0.056 (2) | 0.059 (2) | 0.012 (2) | 0.012 (2) | −0.0119 (19) |
Geometric parameters (Å, º) top
S1—O3 | 1.426 (3) | C4—C5 | 1.360 (7) |
S1—O4 | 1.433 (3) | C5—C6 | 1.395 (6) |
S1—N1 | 1.613 (3) | C7—C8 | 1.525 (6) |
S1—C1 | 1.776 (3) | C7—C10 | 1.537 (5) |
O1—N2 | 1.212 (5) | C3—H3 | 0.9500 |
O2—N2 | 1.200 (5) | C4—H4 | 0.9400 |
O5—C8 | 1.191 (5) | C5—H5 | 0.9600 |
O6—C8 | 1.322 (5) | C6—H6 | 0.9500 |
O6—C9 | 1.455 (6) | C7—H7 | 0.9500 |
N1—C7 | 1.468 (5) | C9—H9A | 0.9500 |
N2—C2 | 1.485 (5) | C9—H9B | 0.9500 |
N1—H1 | 0.8600 | C9—H9C | 0.9300 |
C1—C2 | 1.393 (5) | C10—H10A | 0.9500 |
C1—C6 | 1.388 (5) | C10—H10B | 0.9600 |
C2—C3 | 1.381 (7) | C10—H10C | 0.9400 |
C3—C4 | 1.365 (8) | | |
| | | |
S1···O1 | 3.015 (3) | N2···O3 | 2.947 (5) |
S1···O1i | 3.431 (3) | C1···O1i | 3.227 (5) |
O1···S1ii | 3.431 (3) | C1···O5 | 3.212 (5) |
O1···S1 | 3.015 (3) | C1···C8 | 3.268 (5) |
O1···O3 | 2.748 (4) | C3···O3viii | 3.276 (6) |
O1···O4ii | 3.019 (5) | C4···O3ix | 3.323 (6) |
O1···N1 | 2.999 (5) | C6···O1i | 3.038 (5) |
O1···C1ii | 3.227 (5) | C6···C8 | 3.311 (6) |
O1···C6ii | 3.038 (5) | C6···O5 | 3.396 (5) |
O3···C3iii | 3.276 (6) | C6···O5i | 3.339 (5) |
O3···C4iv | 3.323 (6) | C8···C1 | 3.268 (5) |
O3···O1 | 2.748 (4) | C8···C6 | 3.311 (6) |
O3···N2 | 2.947 (5) | C9···O4x | 3.151 (6) |
O4···O1i | 3.019 (5) | C10···O4ii | 3.344 (5) |
O4···C9v | 3.151 (6) | C3···H9Axi | 3.0600 |
O4···C10i | 3.344 (5) | C10···H5v | 2.9400 |
O4···N1i | 3.125 (3) | H1···O1 | 2.3900 |
O5···C6 | 3.396 (5) | H1···O4ii | 2.3700 |
O5···C6ii | 3.339 (5) | H1···O5 | 2.7500 |
O5···C1 | 3.212 (5) | H1···H10C | 2.5400 |
O5···N1 | 2.911 (4) | H3···O2 | 2.5500 |
O1···H4iii | 2.7700 | H3···O3viii | 2.4400 |
O1···H1 | 2.3900 | H4···O1viii | 2.7700 |
O1···H6ii | 2.9100 | H4···O3ix | 2.8600 |
O2···H9Avi | 2.9200 | H5···C10x | 2.9400 |
O2···H3 | 2.5500 | H5···H10Ax | 2.5900 |
O3···H4iv | 2.8600 | H6···O1i | 2.9100 |
O3···H3iii | 2.4400 | H6···O4 | 2.4000 |
O4···H9Cv | 2.8900 | H6···O5i | 2.5300 |
O4···H10Ci | 2.7100 | H7···O4 | 2.4900 |
O4···H1i | 2.3700 | H9A···O2xii | 2.9200 |
O4···H6 | 2.4000 | H9A···C3xiii | 3.0600 |
O4···H7 | 2.4900 | H9B···O5 | 2.2900 |
O5···H1 | 2.7500 | H9B···H10Bvii | 2.4700 |
O5···H6ii | 2.5300 | H9C···O4x | 2.8900 |
O5···H9B | 2.2900 | H10A···H5v | 2.5900 |
O5···H10C | 2.9000 | H10B···O5xiv | 2.8400 |
O5···H10Bvii | 2.8400 | H10B···H9Bxiv | 2.4700 |
N1···O1 | 2.999 (5) | H10C···O4ii | 2.7100 |
N1···O4ii | 3.125 (3) | H10C···O5 | 2.9000 |
N1···O5 | 2.911 (4) | H10C···H1 | 2.5400 |
| | | |
O3—S1—O4 | 119.29 (18) | O6—C8—C7 | 110.3 (3) |
O3—S1—N1 | 108.52 (17) | O5—C8—O6 | 125.0 (4) |
O3—S1—C1 | 108.05 (17) | O5—C8—C7 | 124.7 (3) |
O4—S1—N1 | 105.97 (18) | C2—C3—H3 | 119.00 |
O4—S1—C1 | 105.97 (15) | C4—C3—H3 | 122.00 |
N1—S1—C1 | 108.66 (15) | C3—C4—H4 | 120.00 |
C8—O6—C9 | 116.2 (4) | C5—C4—H4 | 120.00 |
S1—N1—C7 | 120.02 (19) | C4—C5—H5 | 121.00 |
O1—N2—O2 | 124.6 (4) | C6—C5—H5 | 118.00 |
O1—N2—C2 | 118.3 (3) | C1—C6—H6 | 120.00 |
O2—N2—C2 | 117.2 (4) | C5—C6—H6 | 121.00 |
S1—N1—H1 | 113.00 | N1—C7—H7 | 108.00 |
C7—N1—H1 | 110.00 | C8—C7—H7 | 109.00 |
S1—C1—C2 | 125.3 (3) | C10—C7—H7 | 108.00 |
C2—C1—C6 | 117.6 (3) | O6—C9—H9A | 108.00 |
S1—C1—C6 | 117.1 (3) | O6—C9—H9B | 108.00 |
N2—C2—C3 | 116.6 (4) | O6—C9—H9C | 110.00 |
C1—C2—C3 | 122.1 (4) | H9A—C9—H9B | 109.00 |
N2—C2—C1 | 121.3 (3) | H9A—C9—H9C | 111.00 |
C2—C3—C4 | 119.2 (5) | H9B—C9—H9C | 111.00 |
C3—C4—C5 | 120.3 (4) | C7—C10—H10A | 110.00 |
C4—C5—C6 | 121.1 (4) | C7—C10—H10B | 109.00 |
C1—C6—C5 | 119.7 (4) | C7—C10—H10C | 110.00 |
N1—C7—C10 | 109.8 (3) | H10A—C10—H10B | 108.00 |
C8—C7—C10 | 108.8 (3) | H10A—C10—H10C | 110.00 |
N1—C7—C8 | 112.2 (3) | H10B—C10—H10C | 109.00 |
| | | |
O3—S1—N1—C7 | −165.3 (3) | O2—N2—C2—C1 | 137.6 (4) |
O4—S1—N1—C7 | −36.1 (3) | C6—C1—C2—N2 | 179.7 (3) |
C1—S1—N1—C7 | 77.5 (3) | C6—C1—C2—C3 | 0.3 (6) |
O3—S1—C1—C2 | −37.3 (4) | S1—C1—C6—C5 | −178.5 (3) |
O3—S1—C1—C6 | 141.1 (3) | C2—C1—C6—C5 | 0.0 (6) |
O4—S1—C1—C2 | −166.2 (3) | S1—C1—C2—N2 | −1.9 (5) |
O4—S1—C1—C6 | 12.2 (3) | S1—C1—C2—C3 | 178.6 (3) |
N1—S1—C1—C2 | 80.3 (3) | N2—C2—C3—C4 | −179.8 (4) |
N1—S1—C1—C6 | −101.3 (3) | C1—C2—C3—C4 | −0.3 (7) |
C9—O6—C8—O5 | 0.0 (6) | C2—C3—C4—C5 | 0.0 (8) |
C9—O6—C8—C7 | −179.5 (4) | C3—C4—C5—C6 | 0.2 (8) |
S1—N1—C7—C10 | 167.4 (2) | C4—C5—C6—C1 | −0.2 (7) |
S1—N1—C7—C8 | −71.6 (3) | N1—C7—C8—O5 | −43.2 (4) |
O2—N2—C2—C3 | −42.9 (6) | N1—C7—C8—O6 | 136.3 (3) |
O1—N2—C2—C1 | −43.1 (5) | C10—C7—C8—O5 | 78.4 (4) |
O1—N2—C2—C3 | 136.4 (4) | C10—C7—C8—O6 | −102.1 (3) |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (iii) −x, y−1/2, −z; (iv) −x, y−1/2, −z+1; (v) −x+1, y−1/2, −z+1; (vi) x−1, y, z−1; (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) x−1, y, z; (xii) x+1, y, z+1; (xiii) x+1, y, z; (xiv) −x+1, y−1/2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.86 | 2.39 | 2.999 (5) | 128 |
N1—H1···O4ii | 0.86 | 2.37 | 3.125 (3) | 147 |
C3—H3···O3viii | 0.95 | 2.44 | 3.276 (6) | 146 |
C6—H6···O4 | 0.95 | 2.40 | 2.820 (5) | 107 |
C6—H6···O5i | 0.95 | 2.53 | 3.339 (5) | 144 |
C7—H7···O4 | 0.95 | 2.49 | 2.863 (4) | 103 |
C9—H9B···O5 | 0.95 | 2.29 | 2.668 (7) | 103 |
Symmetry codes: (i) x, y, z+1; (ii) x, y, z−1; (viii) −x, y+1/2, −z. |