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S-Benzyl-
L-cysteine, C
10H
13NO
2S, 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
CCDC reference: 170308
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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.
|
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
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.
Crystal data top
C10H13NO2S | Dx = 1.361 Mg m−3 |
Mr = 211.28 | Melting point: 481 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.4224 (2) Å | Cell parameters from 18971 reflections |
b = 5.0947 (1) Å | θ = 2.9–27.5° |
c = 21.5510 (7) Å | µ = 0.29 mm−1 |
β = 94.8950 (9)° | T = 293 K |
V = 1030.77 (4) Å3 | Rod, colourless |
Z = 4 | 0.10 × 0.05 × 0.04 mm |
F(000) = 448 | |
Data collection top
Enraf-Nonius KappaCCD diffractometer | 4668 independent reflections |
Radiation source: fine-focus sealed tube | 3425 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.159 |
combination of ω and φ scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SORTAV; Enraf-Nonius, 1999) | h = −12→10 |
Tmin = 0.987, Tmax = 0.989 | k = −6→6 |
12824 measured reflections | l = −28→27 |
Refinement top
Refinement on F2 | Hydrogen site location: geom (CH) and difmap (NH) |
Least-squares matrix: full | H-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 = 0.99 | Δρmax = 0.42 e Å−3 |
4668 reflections | Δρmin = −0.54 e Å−3 |
254 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.011 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.46331 (10) | 1.11851 (18) | 0.21713 (4) | 0.0267 (3) | |
O1 | 0.1623 (2) | 0.8349 (5) | 0.04598 (11) | 0.0207 (6) | |
O2 | 0.2276 (3) | 0.4435 (5) | 0.08454 (12) | 0.0240 (6) | |
N1 | 0.4283 (3) | 1.0318 (5) | 0.07619 (12) | 0.0172 (6) | |
H1A | 0.3756 | 1.1752 | 0.0825 | 0.021* | |
H1B | 0.4202 | 0.9908 | 0.0354 | 0.021* | |
H1C | 0.5202 | 1.0645 | 0.0887 | 0.021* | |
C1 | 0.2457 (4) | 0.6805 (7) | 0.07759 (15) | 0.0168 (8) | |
C2 | 0.3768 (4) | 0.8085 (7) | 0.11256 (15) | 0.0174 (8) | |
H21 | 0.4528 | 0.6779 | 0.1195 | 0.021* | |
C3 | 0.3335 (4) | 0.9074 (8) | 0.17537 (15) | 0.0205 (8) | |
H31 | 0.3167 | 0.7570 | 0.2013 | 0.025* | |
H32 | 0.2444 | 1.0025 | 0.1684 | 0.025* | |
C4 | 0.6018 (4) | 0.8877 (9) | 0.24731 (16) | 0.0284 (9) | |
H41 | 0.5912 | 0.7247 | 0.2241 | 0.034* | |
H42 | 0.6946 | 0.9602 | 0.2408 | 0.034* | |
C5 | 0.5953 (4) | 0.8308 (8) | 0.31577 (17) | 0.0265 (9) | |
C6 | 0.6746 (5) | 0.9809 (11) | 0.35949 (19) | 0.0433 (11) | |
H61 | 0.7327 | 1.1148 | 0.3468 | 0.052* | |
C7 | 0.6668 (6) | 0.9295 (11) | 0.4233 (2) | 0.0534 (14) | |
H71 | 0.7204 | 1.0298 | 0.4527 | 0.064* | |
C8 | 0.5814 (5) | 0.7341 (10) | 0.4423 (2) | 0.0458 (12) | |
H81 | 0.5771 | 0.7017 | 0.4846 | 0.055* | |
C9 | 0.5016 (5) | 0.5851 (10) | 0.39901 (19) | 0.0450 (11) | |
H91 | 0.4424 | 0.4532 | 0.4118 | 0.054* | |
C10 | 0.5103 (5) | 0.6335 (9) | 0.33596 (19) | 0.0398 (10) | |
H101 | 0.4575 | 0.5306 | 0.3068 | 0.048* | |
S2 | −0.08617 (12) | 0.37634 (18) | 0.21438 (4) | 0.0309 (3) | |
O3 | −0.3769 (2) | 0.5097 (5) | 0.05489 (11) | 0.0196 (5) | |
O4 | −0.2800 (2) | 0.1397 (5) | 0.09592 (11) | 0.0204 (5) | |
N2 | −0.1222 (3) | 0.7327 (6) | 0.04447 (13) | 0.0171 (6) | |
H2A | −0.1790 | 0.8639 | 0.0554 | 0.021* | |
H2B | −0.1514 | 0.6775 | 0.0058 | 0.021* | |
H2C | −0.0319 | 0.7907 | 0.0452 | 0.021* | |
C11 | −0.2744 (3) | 0.3746 (7) | 0.07859 (15) | 0.0168 (7) | |
C12 | −0.1296 (4) | 0.5098 (7) | 0.08928 (15) | 0.0175 (7) | |
H121 | −0.0546 | 0.3829 | 0.0821 | 0.021* | |
C13 | −0.1006 (4) | 0.6252 (8) | 0.15456 (15) | 0.0219 (7) | |
H131 | −0.1770 | 0.7448 | 0.1625 | 0.026* | |
H132 | −0.0127 | 0.7253 | 0.1565 | 0.026* | |
C14 | −0.0065 (5) | 0.5798 (9) | 0.27778 (16) | 0.0354 (10) | |
H141 | 0.0712 | 0.6818 | 0.2634 | 0.042* | |
H142 | −0.0771 | 0.7005 | 0.2914 | 0.042* | |
C15 | 0.0484 (4) | 0.4066 (8) | 0.33126 (17) | 0.0271 (9) | |
C16 | 0.1598 (4) | 0.2400 (10) | 0.3240 (2) | 0.0394 (11) | |
H161 | 0.2009 | 0.2355 | 0.2863 | 0.047* | |
C17 | 0.2123 (5) | 0.0764 (11) | 0.3729 (2) | 0.0503 (13) | |
H171 | 0.2875 | −0.0374 | 0.3677 | 0.060* | |
C18 | 0.1520 (5) | 0.0858 (11) | 0.4282 (2) | 0.0476 (13) | |
H181 | 0.1865 | −0.0224 | 0.4608 | 0.057* | |
C19 | 0.0422 (6) | 0.2517 (10) | 0.43601 (19) | 0.0459 (12) | |
H191 | 0.0024 | 0.2568 | 0.4740 | 0.055* | |
C20 | −0.0112 (5) | 0.4134 (9) | 0.38788 (19) | 0.0366 (10) | |
H201 | −0.0867 | 0.5261 | 0.3935 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0342 (5) | 0.0315 (5) | 0.0134 (5) | −0.0019 (5) | −0.0045 (4) | −0.0061 (4) |
O1 | 0.0178 (12) | 0.0269 (13) | 0.0165 (13) | −0.0021 (11) | −0.0040 (10) | 0.0047 (11) |
O2 | 0.0238 (14) | 0.0217 (13) | 0.0259 (15) | −0.0008 (11) | −0.0019 (11) | 0.0004 (11) |
N1 | 0.0185 (14) | 0.0240 (16) | 0.0085 (14) | −0.0041 (13) | −0.0017 (11) | −0.0034 (12) |
C1 | 0.0179 (17) | 0.0223 (19) | 0.0107 (17) | 0.0007 (14) | 0.0039 (13) | −0.0025 (14) |
C2 | 0.0211 (17) | 0.0197 (18) | 0.0109 (17) | 0.0000 (14) | −0.0016 (14) | 0.0001 (13) |
C3 | 0.0182 (17) | 0.031 (2) | 0.0126 (17) | 0.0004 (17) | 0.0007 (13) | −0.0023 (16) |
C4 | 0.0258 (19) | 0.043 (2) | 0.0153 (18) | 0.0034 (19) | −0.0034 (14) | −0.0037 (19) |
C5 | 0.029 (2) | 0.035 (2) | 0.0149 (19) | 0.0086 (18) | −0.0031 (15) | −0.0063 (17) |
C6 | 0.043 (3) | 0.058 (3) | 0.026 (2) | −0.006 (2) | −0.0104 (19) | −0.005 (2) |
C7 | 0.071 (3) | 0.067 (4) | 0.018 (2) | −0.004 (3) | −0.017 (2) | −0.012 (2) |
C8 | 0.067 (3) | 0.050 (3) | 0.020 (2) | 0.018 (3) | −0.002 (2) | −0.001 (2) |
C9 | 0.070 (3) | 0.041 (3) | 0.024 (2) | 0.001 (3) | 0.003 (2) | 0.004 (2) |
C10 | 0.059 (3) | 0.037 (2) | 0.022 (2) | −0.001 (2) | −0.0042 (19) | −0.005 (2) |
S2 | 0.0453 (6) | 0.0316 (5) | 0.0138 (5) | −0.0124 (5) | −0.0096 (4) | 0.0055 (4) |
O3 | 0.0158 (12) | 0.0295 (13) | 0.0132 (12) | 0.0004 (11) | −0.0002 (9) | 0.0004 (11) |
O4 | 0.0230 (13) | 0.0199 (12) | 0.0181 (13) | −0.0023 (11) | 0.0002 (10) | −0.0002 (11) |
N2 | 0.0153 (14) | 0.0229 (14) | 0.0127 (15) | −0.0026 (13) | −0.0007 (11) | −0.0004 (12) |
C11 | 0.0163 (17) | 0.0243 (18) | 0.0100 (16) | −0.0012 (16) | 0.0025 (13) | −0.0029 (16) |
C12 | 0.0208 (18) | 0.0190 (16) | 0.0125 (17) | 0.0000 (15) | −0.0007 (14) | 0.0020 (14) |
C13 | 0.0313 (19) | 0.0227 (16) | 0.0108 (17) | −0.0074 (19) | −0.0035 (14) | 0.0017 (17) |
C14 | 0.050 (2) | 0.041 (2) | 0.014 (2) | −0.006 (2) | −0.0077 (18) | −0.0020 (19) |
C15 | 0.035 (2) | 0.030 (2) | 0.0150 (18) | −0.0072 (18) | −0.0062 (15) | −0.0006 (17) |
C16 | 0.035 (2) | 0.057 (3) | 0.026 (2) | −0.005 (2) | −0.0008 (19) | −0.005 (2) |
C17 | 0.043 (3) | 0.060 (3) | 0.045 (3) | 0.013 (3) | −0.013 (2) | 0.001 (3) |
C18 | 0.061 (3) | 0.053 (3) | 0.025 (2) | −0.002 (3) | −0.017 (2) | 0.010 (2) |
C19 | 0.070 (3) | 0.053 (3) | 0.015 (2) | −0.009 (3) | 0.005 (2) | 0.003 (2) |
C20 | 0.045 (2) | 0.044 (3) | 0.021 (2) | 0.003 (2) | 0.0019 (18) | −0.007 (2) |
Geometric parameters (Å, º) top
S1—C3 | 1.810 (3) | S2—C13 | 1.805 (4) |
S1—C4 | 1.834 (4) | S2—C14 | 1.825 (4) |
O1—C1 | 1.268 (4) | O3—C11 | 1.258 (4) |
O2—C1 | 1.230 (4) | O4—C11 | 1.256 (4) |
N1—C2 | 1.486 (4) | N2—C12 | 1.496 (4) |
N1—H1A | 0.9000 | N2—H2A | 0.9000 |
N1—H1B | 0.9000 | N2—H2B | 0.9000 |
N1—H1C | 0.9000 | N2—H2C | 0.9000 |
C1—C2 | 1.536 (4) | C11—C12 | 1.528 (5) |
C2—C3 | 1.532 (5) | C12—C13 | 1.528 (5) |
C2—H21 | 0.9800 | C12—H121 | 0.9800 |
C3—H31 | 0.9700 | C13—H131 | 0.9700 |
C3—H32 | 0.9700 | C13—H132 | 0.9700 |
C4—C5 | 1.510 (5) | C14—C15 | 1.508 (5) |
C4—H41 | 0.9700 | C14—H141 | 0.9700 |
C4—H42 | 0.9700 | C14—H142 | 0.9700 |
C5—C10 | 1.379 (6) | C15—C16 | 1.369 (6) |
C5—C6 | 1.382 (6) | C15—C20 | 1.386 (6) |
C6—C7 | 1.407 (6) | C16—C17 | 1.399 (6) |
C6—H61 | 0.9300 | C16—H161 | 0.9300 |
C7—C8 | 1.365 (7) | C17—C18 | 1.365 (7) |
C7—H71 | 0.9300 | C17—H171 | 0.9300 |
C8—C9 | 1.375 (6) | C18—C19 | 1.358 (7) |
C8—H81 | 0.9300 | C18—H181 | 0.9300 |
C9—C10 | 1.390 (6) | C19—C20 | 1.385 (6) |
C9—H91 | 0.9300 | C19—H191 | 0.9300 |
C10—H101 | 0.9300 | C20—H201 | 0.9300 |
| | | |
C3—S1—C4 | 103.04 (18) | C13—S2—C14 | 97.86 (17) |
C2—N1—H1A | 109.5 | C12—N2—H2A | 109.5 |
C2—N1—H1B | 109.5 | C12—N2—H2B | 109.5 |
H1A—N1—H1B | 109.5 | H2A—N2—H2B | 109.5 |
C2—N1—H1C | 109.5 | C12—N2—H2C | 109.5 |
H1A—N1—H1C | 109.5 | H2A—N2—H2C | 109.5 |
H1B—N1—H1C | 109.5 | H2B—N2—H2C | 109.5 |
O2—C1—O1 | 126.0 (3) | O4—C11—O3 | 126.3 (3) |
O2—C1—C2 | 118.1 (3) | O4—C11—C12 | 116.4 (3) |
O1—C1—C2 | 115.8 (3) | O3—C11—C12 | 117.3 (3) |
N1—C2—C3 | 109.8 (3) | N2—C12—C13 | 106.7 (3) |
N1—C2—C1 | 110.6 (3) | N2—C12—C11 | 109.6 (3) |
C3—C2—C1 | 108.1 (3) | C13—C12—C11 | 113.6 (3) |
N1—C2—H21 | 109.5 | N2—C12—H121 | 109.0 |
C3—C2—H21 | 109.5 | C13—C12—H121 | 109.0 |
C1—C2—H21 | 109.5 | C11—C12—H121 | 109.0 |
C2—C3—S1 | 114.6 (2) | C12—C13—S2 | 112.6 (3) |
C2—C3—H31 | 108.6 | C12—C13—H131 | 109.1 |
S1—C3—H31 | 108.6 | S2—C13—H131 | 109.1 |
C2—C3—H32 | 108.6 | C12—C13—H132 | 109.1 |
S1—C3—H32 | 108.6 | S2—C13—H132 | 109.1 |
H31—C3—H32 | 107.6 | H131—C13—H132 | 107.8 |
C5—C4—S1 | 112.5 (3) | C15—C14—S2 | 109.4 (3) |
C5—C4—H41 | 109.1 | C15—C14—H141 | 109.8 |
S1—C4—H41 | 109.1 | S2—C14—H141 | 109.8 |
C5—C4—H42 | 109.1 | C15—C14—H142 | 109.8 |
S1—C4—H42 | 109.1 | S2—C14—H142 | 109.8 |
H41—C4—H42 | 107.8 | H141—C14—H142 | 108.2 |
C10—C5—C6 | 118.9 (4) | C16—C15—C20 | 119.2 (4) |
C10—C5—C4 | 121.4 (4) | C16—C15—C14 | 119.5 (4) |
C6—C5—C4 | 119.7 (4) | C20—C15—C14 | 121.3 (4) |
C5—C6—C7 | 119.5 (5) | C15—C16—C17 | 120.6 (4) |
C5—C6—H61 | 120.2 | C15—C16—H161 | 119.7 |
C7—C6—H61 | 120.2 | C17—C16—H161 | 119.7 |
C8—C7—C6 | 120.7 (5) | C18—C17—C16 | 119.3 (5) |
C8—C7—H71 | 119.7 | C18—C17—H171 | 120.3 |
C6—C7—H71 | 119.7 | C16—C17—H171 | 120.3 |
C7—C8—C9 | 120.1 (4) | C19—C18—C17 | 120.6 (4) |
C7—C8—H81 | 120.0 | C19—C18—H181 | 119.7 |
C9—C8—H81 | 120.0 | C17—C18—H181 | 119.7 |
C8—C9—C10 | 119.4 (5) | C18—C19—C20 | 120.6 (4) |
C8—C9—H91 | 120.3 | C18—C19—H191 | 119.7 |
C10—C9—H91 | 120.3 | C20—C19—H191 | 119.7 |
C5—C10—C9 | 121.5 (4) | C19—C20—C15 | 119.7 (4) |
C5—C10—H101 | 119.3 | C19—C20—H201 | 120.1 |
C9—C10—H101 | 119.3 | C15—C20—H201 | 120.1 |
| | | |
C1—C2—C3—S1 | −168.9 (2) | C11—C12—C13—S2 | 65.5 (3) |
C2—C3—S1—C4 | −75.2 (3) | C12—C13—S2—C14 | 165.5 (3) |
C3—S1—C4—C5 | −103.1 (3) | C13—S2—C14—C15 | −167.3 (3) |
N1—C2—C3—S1 | −48.2 (3) | N2—C12—C13—S2 | −173.7 (2) |
O1—C1—C2—C3 | 85.7 (3) | O3—C11—C12—C13 | 93.6 (4) |
O2—C1—C2—C3 | −91.3 (4) | O4—C11—C12—C13 | −84.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2i | 0.90 | 1.96 | 2.841 (4) | 167 |
N1—H1C···O4ii | 0.90 | 1.91 | 2.800 (3) | 167 |
N1—H1B···O3iii | 0.90 | 1.96 | 2.827 (3) | 162 |
N2—H2A···O4i | 0.90 | 1.95 | 2.832 (4) | 168 |
N2—H2C···O1 | 0.90 | 1.84 | 2.729 (4) | 168 |
N2—H2B···O1iv | 0.90 | 2.07 | 2.815 (4) | 140 |
N2—H2B···O2iii | 0.90 | 2.43 | 3.066 (4) | 128 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) −x, y+1/2, −z; (iv) −x, y−1/2, −z. |
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