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In the title compound, C
5H
10NO
2+·C
2Cl
3O
2−, the proline molecule exists as a cation with a positively charged amino group and a neutral carboxylic acid group. The trichloroacetic acid molecule is in the anionic state. The 3
1-screw-related proline cations and trichloroacetate anions are linked by N—H
O and O—H
O hydrogen bonds to form molecular columns along the
c axis. No head-to-tail hydrogen bonds are observed.
Supporting information
CCDC reference: 206756
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.002 Å
- R factor = 0.026
- wR factor = 0.069
- Data-to-parameter ratio = 24.6
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 35.03
From the CIF: _reflns_number_total 4363
Count of symmetry unique reflns 2447
Completeness (_total/calc) 178.30%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1916
Fraction of Friedel pairs measured 0.783
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.
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
L-prolinium trichloroacetate
top
Crystal data top
C5H10NO2+·C2Cl3O2− | Dx = 1.669 Mg m−3 Dm = 1.65 Mg m−3 Dm measured by flotation in a mixture of xylene and bromoform |
Mr = 278.51 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P31 | Cell parameters from 1024 reflections |
Hall symbol: P 31 | θ = 3–35° |
a = 9.7541 (14) Å | µ = 0.82 mm−1 |
c = 10.089 (2) Å | T = 105 K |
V = 831.3 (2) Å3 | Prismatic, colourless |
Z = 3 | 0.5 × 0.4 × 0.3 mm |
F(000) = 426 | |
Data collection top
Bruker SMART diffractometer | 4363 independent reflections |
Radiation source: fine-focus sealed tube | 4258 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 8 pixels mm-1 | θmax = 35.0°, θmin = 2.4° |
ω scans | h = −14→15 |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | k = −15→15 |
Tmin = 0.664, Tmax = 0.782 | l = −15→16 |
13374 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | All H-atom parameters refined |
R[F2 > 2σ(F2)] = 0.026 | w = 1/[σ2(Fo2) + (0.041P)2 + 0.1873P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.069 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.45 e Å−3 |
4363 reflections | Δρmin = −0.42 e Å−3 |
177 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.008 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1915 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.00 (3) |
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 | |
Cl1 | 0.15562 (4) | 0.58351 (4) | 0.80263 (4) | 0.03181 (8) | |
Cl2 | −0.14731 (4) | 0.56751 (4) | 0.79662 (4) | 0.03248 (8) | |
Cl3 | −0.02231 (6) | 0.50100 (4) | 0.56123 (3) | 0.03624 (10) | |
N1 | 0.21536 (11) | 0.16603 (11) | 0.62088 (9) | 0.01506 (14) | |
O1 | 0.11683 (13) | 0.33330 (12) | 0.34074 (9) | 0.02341 (17) | |
O2 | 0.13140 (13) | 0.11106 (11) | 0.36345 (9) | 0.02372 (17) | |
O3 | 0.19102 (12) | 0.89718 (10) | 0.75413 (9) | 0.02275 (17) | |
O4 | 0.06676 (13) | 0.83180 (11) | 0.55830 (9) | 0.02325 (17) | |
C1 | 0.14132 (13) | 0.23136 (12) | 0.40733 (10) | 0.01616 (16) | |
C2 | 0.19069 (13) | 0.28623 (12) | 0.54964 (10) | 0.01583 (16) | |
C3 | 0.35348 (17) | 0.43601 (14) | 0.55455 (13) | 0.0242 (2) | |
C4 | 0.46725 (15) | 0.37208 (17) | 0.53572 (13) | 0.0265 (2) | |
C5 | 0.38786 (15) | 0.21247 (15) | 0.60752 (15) | 0.0244 (2) | |
C6 | 0.10354 (13) | 0.80177 (12) | 0.66771 (11) | 0.01622 (16) | |
C7 | 0.02752 (13) | 0.62085 (12) | 0.70449 (11) | 0.01681 (17) | |
H1O | 0.111 (3) | 0.314 (3) | 0.254 (3) | 0.046 (7)* | |
H1N | 0.158 (3) | 0.080 (3) | 0.595 (2) | 0.029 (5)* | |
H2N | 0.192 (2) | 0.167 (2) | 0.704 (2) | 0.019 (4)* | |
H2 | 0.112 (3) | 0.298 (3) | 0.588 (2) | 0.034 (6)* | |
H3A | 0.364 (3) | 0.508 (3) | 0.485 (3) | 0.037 (6)* | |
H3B | 0.358 (3) | 0.480 (3) | 0.638 (3) | 0.039 (6)* | |
H4A | 0.483 (3) | 0.356 (3) | 0.444 (3) | 0.042 (7)* | |
H4B | 0.565 (3) | 0.437 (3) | 0.572 (2) | 0.036 (6)* | |
H5A | 0.394 (3) | 0.130 (3) | 0.559 (2) | 0.034 (6)* | |
H5B | 0.433 (3) | 0.220 (3) | 0.703 (3) | 0.042 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.02881 (15) | 0.02128 (13) | 0.0471 (2) | 0.01383 (12) | −0.01275 (13) | 0.00373 (12) |
Cl2 | 0.02354 (13) | 0.02782 (15) | 0.04450 (19) | 0.01165 (11) | 0.01497 (12) | 0.01044 (12) |
Cl3 | 0.0649 (3) | 0.02013 (13) | 0.02403 (13) | 0.02154 (15) | −0.00642 (14) | −0.00640 (10) |
N1 | 0.0163 (4) | 0.0132 (3) | 0.0158 (3) | 0.0074 (3) | 0.0017 (3) | 0.0012 (3) |
O1 | 0.0358 (5) | 0.0252 (4) | 0.0156 (3) | 0.0201 (4) | −0.0036 (3) | −0.0010 (3) |
O2 | 0.0339 (5) | 0.0168 (3) | 0.0197 (4) | 0.0121 (3) | −0.0028 (3) | −0.0036 (3) |
O3 | 0.0321 (4) | 0.0146 (3) | 0.0155 (3) | 0.0071 (3) | −0.0023 (3) | 0.0006 (3) |
O4 | 0.0321 (5) | 0.0187 (4) | 0.0184 (3) | 0.0122 (3) | −0.0054 (3) | 0.0009 (3) |
C1 | 0.0166 (4) | 0.0146 (4) | 0.0154 (4) | 0.0064 (3) | 0.0003 (3) | 0.0004 (3) |
C2 | 0.0202 (4) | 0.0148 (4) | 0.0143 (4) | 0.0102 (3) | 0.0007 (3) | 0.0001 (3) |
C3 | 0.0288 (6) | 0.0126 (4) | 0.0243 (5) | 0.0052 (4) | −0.0067 (4) | −0.0008 (4) |
C4 | 0.0167 (4) | 0.0259 (6) | 0.0269 (6) | 0.0032 (4) | 0.0016 (4) | 0.0031 (4) |
C5 | 0.0176 (5) | 0.0214 (5) | 0.0357 (6) | 0.0109 (4) | 0.0022 (4) | 0.0016 (4) |
C6 | 0.0185 (4) | 0.0136 (4) | 0.0166 (4) | 0.0081 (3) | 0.0014 (3) | 0.0012 (3) |
C7 | 0.0172 (4) | 0.0141 (4) | 0.0188 (4) | 0.0076 (3) | 0.0000 (3) | 0.0010 (3) |
Geometric parameters (Å, º) top
Cl1—C7 | 1.7689 (12) | C1—C2 | 1.5238 (15) |
Cl2—C7 | 1.7764 (12) | C2—C3 | 1.5292 (17) |
Cl3—C7 | 1.7674 (11) | C2—H2 | 0.92 (2) |
N1—C2 | 1.4938 (14) | C3—C4 | 1.532 (2) |
N1—C5 | 1.5139 (16) | C3—H3A | 0.96 (3) |
N1—H1N | 0.79 (2) | C3—H3B | 0.94 (3) |
N1—H2N | 0.87 (2) | C4—C5 | 1.5305 (19) |
O1—C1 | 1.3171 (14) | C4—H4A | 0.97 (3) |
O1—H1O | 0.89 (3) | C4—H4B | 0.92 (3) |
O2—C1 | 1.2118 (14) | C5—H5A | 0.96 (3) |
O3—C6 | 1.2491 (14) | C5—H5B | 1.05 (3) |
O4—C6 | 1.2402 (14) | C6—C7 | 1.5790 (15) |
| | | |
C2—N1—C5 | 108.27 (9) | C5—C4—C3 | 104.72 (10) |
C2—N1—H1N | 111.9 (17) | C5—C4—H4A | 109.4 (16) |
C5—N1—H1N | 112.0 (17) | C3—C4—H4A | 112.8 (17) |
C2—N1—H2N | 107.6 (14) | C5—C4—H4B | 109.5 (16) |
C5—N1—H2N | 110.2 (14) | C3—C4—H4B | 113.1 (16) |
H1N—N1—H2N | 107 (2) | H4A—C4—H4B | 107 (2) |
C1—O1—H1O | 111.1 (18) | N1—C5—C4 | 105.54 (10) |
O2—C1—O1 | 126.00 (10) | N1—C5—H5A | 108.5 (15) |
O2—C1—C2 | 122.85 (10) | C4—C5—H5A | 113.3 (14) |
O1—C1—C2 | 111.12 (9) | N1—C5—H5B | 107.5 (16) |
N1—C2—C1 | 108.92 (8) | C4—C5—H5B | 112.4 (16) |
N1—C2—C3 | 103.68 (9) | H5A—C5—H5B | 109 (2) |
C1—C2—C3 | 111.15 (9) | O4—C6—O3 | 128.01 (11) |
N1—C2—H2 | 111.7 (15) | O4—C6—C7 | 116.33 (10) |
C1—C2—H2 | 107.6 (15) | O3—C6—C7 | 115.64 (9) |
C3—C2—H2 | 113.8 (16) | C6—C7—Cl3 | 111.54 (7) |
C2—C3—C4 | 102.98 (9) | C6—C7—Cl1 | 112.11 (7) |
C2—C3—H3A | 110.8 (16) | Cl3—C7—Cl1 | 108.09 (6) |
C4—C3—H3A | 112.2 (15) | C6—C7—Cl2 | 107.21 (7) |
C2—C3—H3B | 104.8 (16) | Cl3—C7—Cl2 | 109.14 (6) |
C4—C3—H3B | 115.0 (17) | Cl1—C7—Cl2 | 108.68 (6) |
H3A—C3—H3B | 111 (2) | | |
| | | |
C5—N1—C2—C1 | 91.81 (11) | C2—N1—C5—C4 | 4.64 (13) |
C5—N1—C2—C3 | −26.62 (11) | C3—C4—C5—N1 | 19.21 (13) |
O2—C1—C2—N1 | −2.43 (15) | O4—C6—C7—Cl3 | 25.75 (13) |
O1—C1—C2—N1 | 179.46 (9) | O3—C6—C7—Cl3 | −155.70 (9) |
O2—C1—C2—C3 | 111.19 (13) | O4—C6—C7—Cl1 | 147.12 (9) |
O1—C1—C2—C3 | −66.92 (13) | O3—C6—C7—Cl1 | −34.32 (13) |
N1—C2—C3—C4 | 37.96 (11) | O4—C6—C7—Cl2 | −93.68 (11) |
C1—C2—C3—C4 | −78.91 (11) | O3—C6—C7—Cl2 | 84.87 (11) |
C2—C3—C4—C5 | −35.30 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4i | 0.79 (2) | 2.15 (2) | 2.8987 (14) | 159 (2) |
O1—H1O···O3ii | 0.89 (3) | 1.69 (3) | 2.5775 (13) | 175 (3) |
N1—H2N···O4iii | 0.87 (2) | 2.06 (2) | 2.9043 (14) | 164 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −y+1, x−y+1, z−2/3; (iii) −y+1, x−y+1, z+1/3. |
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