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S-Benzyl-L-cysteine, C10H13NO2S, contains two mol­ecules in the asymmetric unit, both of which are zwitterions. They differ principally in terms of molecular conformation about their Cα—Cβ bonds; one is approximately anti, the other gauche for the N—C—C—S grouping. The N—H...O hydrogen-bonding scheme has been elucidated.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801008340/bt6050sup1.cif
Contains datablocks I, s92ta

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801008340/bt6050Isup2.hkl
Contains datablock I

CCDC reference: 170308

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.062
  • wR factor = 0.160
  • Data-to-parameter ratio = 18.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Amber Alert Alert Level B:
RINTA_01 Alert B The value of Rint is greater than 0.15 Rint given 0.159
Author response: In our opinion, this merely reflects the poor crystal quality. Merging in triclinic symmetry led to essentially the same residual.

Yellow Alert Alert Level C:
PLAT_030 Alert C Refined Extinction parameter within range .... 2.75 Sigma General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.51 From the CIF: _reflns_number_total 4668 Count of symmetry unique reflns 2647 Completeness (_total/calc) 176.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2021 Fraction of Friedel pairs measured 0.764 Are heavy atom types Z>Si present yes 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.
0 Alert Level A = Potentially serious problem
1 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

Data collection: KappaCCD Software (Nonius, 1999); cell refinement: KappaCCD Software; data reduction: KappaCCD Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

S-benzyl-L-cysteine top
Crystal data top
C10H13NO2SDx = 1.361 Mg m3
Mr = 211.28Melting point: 481 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.4224 (2) ÅCell parameters from 18971 reflections
b = 5.0947 (1) Åθ = 2.9–27.5°
c = 21.5510 (7) ŵ = 0.29 mm1
β = 94.8950 (9)°T = 293 K
V = 1030.77 (4) Å3Rod, colourless
Z = 40.10 × 0.05 × 0.04 mm
F(000) = 448
Data collection top
Enraf-Nonius KappaCCD
diffractometer
4668 independent reflections
Radiation source: fine-focus sealed tube3425 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.159
combination of ω and φ scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SORTAV; Enraf-Nonius, 1999)
h = 1210
Tmin = 0.987, Tmax = 0.989k = 66
12824 measured reflectionsl = 2827
Refinement top
Refinement on F2Hydrogen site location: geom (CH) and difmap (NH)
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.062 w = 1/[σ2(Fo2) + (0.0732P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.160(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.42 e Å3
4668 reflectionsΔρmin = 0.54 e Å3
254 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.011 (4)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.19 (10)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.46331 (10)1.11851 (18)0.21713 (4)0.0267 (3)
O10.1623 (2)0.8349 (5)0.04598 (11)0.0207 (6)
O20.2276 (3)0.4435 (5)0.08454 (12)0.0240 (6)
N10.4283 (3)1.0318 (5)0.07619 (12)0.0172 (6)
H1A0.37561.17520.08250.021*
H1B0.42020.99080.03540.021*
H1C0.52021.06450.08870.021*
C10.2457 (4)0.6805 (7)0.07759 (15)0.0168 (8)
C20.3768 (4)0.8085 (7)0.11256 (15)0.0174 (8)
H210.45280.67790.11950.021*
C30.3335 (4)0.9074 (8)0.17537 (15)0.0205 (8)
H310.31670.75700.20130.025*
H320.24441.00250.16840.025*
C40.6018 (4)0.8877 (9)0.24731 (16)0.0284 (9)
H410.59120.72470.22410.034*
H420.69460.96020.24080.034*
C50.5953 (4)0.8308 (8)0.31577 (17)0.0265 (9)
C60.6746 (5)0.9809 (11)0.35949 (19)0.0433 (11)
H610.73271.11480.34680.052*
C70.6668 (6)0.9295 (11)0.4233 (2)0.0534 (14)
H710.72041.02980.45270.064*
C80.5814 (5)0.7341 (10)0.4423 (2)0.0458 (12)
H810.57710.70170.48460.055*
C90.5016 (5)0.5851 (10)0.39901 (19)0.0450 (11)
H910.44240.45320.41180.054*
C100.5103 (5)0.6335 (9)0.33596 (19)0.0398 (10)
H1010.45750.53060.30680.048*
S20.08617 (12)0.37634 (18)0.21438 (4)0.0309 (3)
O30.3769 (2)0.5097 (5)0.05489 (11)0.0196 (5)
O40.2800 (2)0.1397 (5)0.09592 (11)0.0204 (5)
N20.1222 (3)0.7327 (6)0.04447 (13)0.0171 (6)
H2A0.17900.86390.05540.021*
H2B0.15140.67750.00580.021*
H2C0.03190.79070.04520.021*
C110.2744 (3)0.3746 (7)0.07859 (15)0.0168 (7)
C120.1296 (4)0.5098 (7)0.08928 (15)0.0175 (7)
H1210.05460.38290.08210.021*
C130.1006 (4)0.6252 (8)0.15456 (15)0.0219 (7)
H1310.17700.74480.16250.026*
H1320.01270.72530.15650.026*
C140.0065 (5)0.5798 (9)0.27778 (16)0.0354 (10)
H1410.07120.68180.26340.042*
H1420.07710.70050.29140.042*
C150.0484 (4)0.4066 (8)0.33126 (17)0.0271 (9)
C160.1598 (4)0.2400 (10)0.3240 (2)0.0394 (11)
H1610.20090.23550.28630.047*
C170.2123 (5)0.0764 (11)0.3729 (2)0.0503 (13)
H1710.28750.03740.36770.060*
C180.1520 (5)0.0858 (11)0.4282 (2)0.0476 (13)
H1810.18650.02240.46080.057*
C190.0422 (6)0.2517 (10)0.43601 (19)0.0459 (12)
H1910.00240.25680.47400.055*
C200.0112 (5)0.4134 (9)0.38788 (19)0.0366 (10)
H2010.08670.52610.39350.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0342 (5)0.0315 (5)0.0134 (5)0.0019 (5)0.0045 (4)0.0061 (4)
O10.0178 (12)0.0269 (13)0.0165 (13)0.0021 (11)0.0040 (10)0.0047 (11)
O20.0238 (14)0.0217 (13)0.0259 (15)0.0008 (11)0.0019 (11)0.0004 (11)
N10.0185 (14)0.0240 (16)0.0085 (14)0.0041 (13)0.0017 (11)0.0034 (12)
C10.0179 (17)0.0223 (19)0.0107 (17)0.0007 (14)0.0039 (13)0.0025 (14)
C20.0211 (17)0.0197 (18)0.0109 (17)0.0000 (14)0.0016 (14)0.0001 (13)
C30.0182 (17)0.031 (2)0.0126 (17)0.0004 (17)0.0007 (13)0.0023 (16)
C40.0258 (19)0.043 (2)0.0153 (18)0.0034 (19)0.0034 (14)0.0037 (19)
C50.029 (2)0.035 (2)0.0149 (19)0.0086 (18)0.0031 (15)0.0063 (17)
C60.043 (3)0.058 (3)0.026 (2)0.006 (2)0.0104 (19)0.005 (2)
C70.071 (3)0.067 (4)0.018 (2)0.004 (3)0.017 (2)0.012 (2)
C80.067 (3)0.050 (3)0.020 (2)0.018 (3)0.002 (2)0.001 (2)
C90.070 (3)0.041 (3)0.024 (2)0.001 (3)0.003 (2)0.004 (2)
C100.059 (3)0.037 (2)0.022 (2)0.001 (2)0.0042 (19)0.005 (2)
S20.0453 (6)0.0316 (5)0.0138 (5)0.0124 (5)0.0096 (4)0.0055 (4)
O30.0158 (12)0.0295 (13)0.0132 (12)0.0004 (11)0.0002 (9)0.0004 (11)
O40.0230 (13)0.0199 (12)0.0181 (13)0.0023 (11)0.0002 (10)0.0002 (11)
N20.0153 (14)0.0229 (14)0.0127 (15)0.0026 (13)0.0007 (11)0.0004 (12)
C110.0163 (17)0.0243 (18)0.0100 (16)0.0012 (16)0.0025 (13)0.0029 (16)
C120.0208 (18)0.0190 (16)0.0125 (17)0.0000 (15)0.0007 (14)0.0020 (14)
C130.0313 (19)0.0227 (16)0.0108 (17)0.0074 (19)0.0035 (14)0.0017 (17)
C140.050 (2)0.041 (2)0.014 (2)0.006 (2)0.0077 (18)0.0020 (19)
C150.035 (2)0.030 (2)0.0150 (18)0.0072 (18)0.0062 (15)0.0006 (17)
C160.035 (2)0.057 (3)0.026 (2)0.005 (2)0.0008 (19)0.005 (2)
C170.043 (3)0.060 (3)0.045 (3)0.013 (3)0.013 (2)0.001 (3)
C180.061 (3)0.053 (3)0.025 (2)0.002 (3)0.017 (2)0.010 (2)
C190.070 (3)0.053 (3)0.015 (2)0.009 (3)0.005 (2)0.003 (2)
C200.045 (2)0.044 (3)0.021 (2)0.003 (2)0.0019 (18)0.007 (2)
Geometric parameters (Å, º) top
S1—C31.810 (3)S2—C131.805 (4)
S1—C41.834 (4)S2—C141.825 (4)
O1—C11.268 (4)O3—C111.258 (4)
O2—C11.230 (4)O4—C111.256 (4)
N1—C21.486 (4)N2—C121.496 (4)
N1—H1A0.9000N2—H2A0.9000
N1—H1B0.9000N2—H2B0.9000
N1—H1C0.9000N2—H2C0.9000
C1—C21.536 (4)C11—C121.528 (5)
C2—C31.532 (5)C12—C131.528 (5)
C2—H210.9800C12—H1210.9800
C3—H310.9700C13—H1310.9700
C3—H320.9700C13—H1320.9700
C4—C51.510 (5)C14—C151.508 (5)
C4—H410.9700C14—H1410.9700
C4—H420.9700C14—H1420.9700
C5—C101.379 (6)C15—C161.369 (6)
C5—C61.382 (6)C15—C201.386 (6)
C6—C71.407 (6)C16—C171.399 (6)
C6—H610.9300C16—H1610.9300
C7—C81.365 (7)C17—C181.365 (7)
C7—H710.9300C17—H1710.9300
C8—C91.375 (6)C18—C191.358 (7)
C8—H810.9300C18—H1810.9300
C9—C101.390 (6)C19—C201.385 (6)
C9—H910.9300C19—H1910.9300
C10—H1010.9300C20—H2010.9300
C3—S1—C4103.04 (18)C13—S2—C1497.86 (17)
C2—N1—H1A109.5C12—N2—H2A109.5
C2—N1—H1B109.5C12—N2—H2B109.5
H1A—N1—H1B109.5H2A—N2—H2B109.5
C2—N1—H1C109.5C12—N2—H2C109.5
H1A—N1—H1C109.5H2A—N2—H2C109.5
H1B—N1—H1C109.5H2B—N2—H2C109.5
O2—C1—O1126.0 (3)O4—C11—O3126.3 (3)
O2—C1—C2118.1 (3)O4—C11—C12116.4 (3)
O1—C1—C2115.8 (3)O3—C11—C12117.3 (3)
N1—C2—C3109.8 (3)N2—C12—C13106.7 (3)
N1—C2—C1110.6 (3)N2—C12—C11109.6 (3)
C3—C2—C1108.1 (3)C13—C12—C11113.6 (3)
N1—C2—H21109.5N2—C12—H121109.0
C3—C2—H21109.5C13—C12—H121109.0
C1—C2—H21109.5C11—C12—H121109.0
C2—C3—S1114.6 (2)C12—C13—S2112.6 (3)
C2—C3—H31108.6C12—C13—H131109.1
S1—C3—H31108.6S2—C13—H131109.1
C2—C3—H32108.6C12—C13—H132109.1
S1—C3—H32108.6S2—C13—H132109.1
H31—C3—H32107.6H131—C13—H132107.8
C5—C4—S1112.5 (3)C15—C14—S2109.4 (3)
C5—C4—H41109.1C15—C14—H141109.8
S1—C4—H41109.1S2—C14—H141109.8
C5—C4—H42109.1C15—C14—H142109.8
S1—C4—H42109.1S2—C14—H142109.8
H41—C4—H42107.8H141—C14—H142108.2
C10—C5—C6118.9 (4)C16—C15—C20119.2 (4)
C10—C5—C4121.4 (4)C16—C15—C14119.5 (4)
C6—C5—C4119.7 (4)C20—C15—C14121.3 (4)
C5—C6—C7119.5 (5)C15—C16—C17120.6 (4)
C5—C6—H61120.2C15—C16—H161119.7
C7—C6—H61120.2C17—C16—H161119.7
C8—C7—C6120.7 (5)C18—C17—C16119.3 (5)
C8—C7—H71119.7C18—C17—H171120.3
C6—C7—H71119.7C16—C17—H171120.3
C7—C8—C9120.1 (4)C19—C18—C17120.6 (4)
C7—C8—H81120.0C19—C18—H181119.7
C9—C8—H81120.0C17—C18—H181119.7
C8—C9—C10119.4 (5)C18—C19—C20120.6 (4)
C8—C9—H91120.3C18—C19—H191119.7
C10—C9—H91120.3C20—C19—H191119.7
C5—C10—C9121.5 (4)C19—C20—C15119.7 (4)
C5—C10—H101119.3C19—C20—H201120.1
C9—C10—H101119.3C15—C20—H201120.1
C1—C2—C3—S1168.9 (2)C11—C12—C13—S265.5 (3)
C2—C3—S1—C475.2 (3)C12—C13—S2—C14165.5 (3)
C3—S1—C4—C5103.1 (3)C13—S2—C14—C15167.3 (3)
N1—C2—C3—S148.2 (3)N2—C12—C13—S2173.7 (2)
O1—C1—C2—C385.7 (3)O3—C11—C12—C1393.6 (4)
O2—C1—C2—C391.3 (4)O4—C11—C12—C1384.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.901.962.841 (4)167
N1—H1C···O4ii0.901.912.800 (3)167
N1—H1B···O3iii0.901.962.827 (3)162
N2—H2A···O4i0.901.952.832 (4)168
N2—H2C···O10.901.842.729 (4)168
N2—H2B···O1iv0.902.072.815 (4)140
N2—H2B···O2iii0.902.433.066 (4)128
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x, y+1/2, z; (iv) x, y1/2, z.
 

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