The title compound C
6H
15N
2O
2+·C
2Cl
3O
2−, crystallizes with one lysinium cation and one trichloroacetate anion in the asymmetric unit. The cations are linked through a number of intermolecular N—H
O hydrogen bonds, forming a slab-like structure in the
ab plane.
Supporting information
CCDC reference: 633206
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.125
- Data-to-parameter ratio = 27.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl3 .. O1 .. 3.00 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A .. CL3 .. 2.98 Ang.
PLAT736_ALERT_1_C H...A Calc 2.050(13), Rep 2.049(4) ...... 3.25 su-Ra
H2A -O2 1.555 2.655
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2
C2 Cl3 O2
Alert level G
REFLT03_ALERT_4_G 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.
From the CIF: _diffrn_reflns_theta_max 34.41
From the CIF: _reflns_number_total 4946
Count of symmetry unique reflns 2834
Completeness (_total/calc) 174.52%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2112
Fraction of Friedel pairs measured 0.745
Are heavy atom types Z>Si present yes
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
4 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
4 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
L-Lysinium trichloroacetate
top
Crystal data top
C6H15N2O2+·C2Cl3O2− | F(000) = 320 |
Mr = 309.57 | Dx = 1.601 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 6860 reflections |
a = 5.7283 (2) Å | θ = 2.6–33.0° |
b = 9.0412 (3) Å | µ = 0.72 mm−1 |
c = 12.4994 (4) Å | T = 293 K |
β = 97.251 (1)° | Needle, colourless |
V = 642.18 (4) Å3 | 0.3 × 0.2 × 0.2 mm |
Z = 2 | |
Data collection top
Bruker APEXII diffractometer | 4946 independent reflections |
Radiation source: fine-focus sealed tube | 4625 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω and φ scans | θmax = 34.4°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −9→9 |
Tmin = 0.81, Tmax = 0.91 | k = −14→14 |
10511 measured reflections | l = −19→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0748P)2 + 0.22P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.008 |
4946 reflections | Δρmax = 0.90 e Å−3 |
178 parameters | Δρmin = −0.52 e Å−3 |
7 restraints | Absolute structure: Flack (1983), with how many Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.04 (6) |
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 | |
C1 | 0.3866 (3) | 1.0223 (2) | 0.04870 (12) | 0.0261 (3) | |
C2 | 0.6303 (2) | 1.03418 (18) | 0.01008 (11) | 0.0233 (2) | |
H2 | 0.6979 | 1.1309 | 0.0314 | 0.028* | |
C3 | 0.6056 (3) | 1.0223 (2) | −0.11266 (12) | 0.0288 (3) | |
H3A | 0.5514 | 0.9236 | −0.1337 | 0.035* | |
H3B | 0.4865 | 1.0918 | −0.1433 | 0.035* | |
C4 | 0.8330 (3) | 1.0529 (2) | −0.16001 (13) | 0.0277 (3) | |
H4A | 0.9487 | 0.9788 | −0.1337 | 0.033* | |
H4B | 0.8936 | 1.1486 | −0.1347 | 0.033* | |
C5 | 0.8027 (3) | 1.0519 (2) | −0.28351 (13) | 0.0294 (3) | |
H5A | 0.9556 | 1.0681 | −0.3071 | 0.035* | |
H5B | 0.7498 | 0.9543 | −0.3080 | 0.035* | |
C6 | 0.6333 (3) | 1.1647 (2) | −0.33822 (12) | 0.0279 (3) | |
H6A | 0.6234 | 1.1526 | −0.4158 | 0.034* | |
H6B | 0.4780 | 1.1474 | −0.3176 | 0.034* | |
C7 | 0.2409 (3) | 0.50713 (19) | −0.35804 (13) | 0.0269 (3) | |
C8 | 0.1016 (3) | 0.6569 (2) | −0.35497 (12) | 0.0273 (3) | |
N1 | 0.7901 (2) | 0.91643 (17) | 0.06129 (11) | 0.0262 (2) | |
N2 | 0.7075 (3) | 1.31828 (19) | −0.30912 (13) | 0.0298 (3) | |
O1 | 0.2558 (3) | 1.1327 (2) | 0.03332 (13) | 0.0401 (3) | |
O2 | 0.3325 (3) | 0.90158 (19) | 0.08859 (13) | 0.0392 (3) | |
O3 | 0.3841 (3) | 0.5030 (2) | −0.42340 (14) | 0.0442 (4) | |
O4 | 0.1931 (2) | 0.40808 (16) | −0.29448 (11) | 0.0306 (2) | |
Cl1 | −0.10432 (12) | 0.66655 (12) | −0.47101 (5) | 0.0646 (2) | |
Cl2 | 0.29770 (15) | 0.80593 (9) | −0.35709 (11) | 0.0814 (3) | |
Cl3 | −0.04997 (12) | 0.66829 (6) | −0.24091 (4) | 0.04799 (15) | |
H1C | 0.743 (4) | 0.8358 (15) | 0.031 (2) | 0.025 (6)* | |
H1A | 0.783 (5) | 0.917 (4) | 0.1288 (4) | 0.034 (7)* | |
H1B | 0.9309 (19) | 0.940 (4) | 0.054 (3) | 0.040 (7)* | |
H2A | 0.691 (5) | 1.335 (3) | −0.2436 (7) | 0.031 (6)* | |
H2C | 0.8557 (10) | 1.308 (5) | −0.306 (3) | 0.054 (9)* | |
H2B | 0.612 (5) | 1.373 (4) | −0.349 (3) | 0.054 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0215 (5) | 0.0373 (8) | 0.0200 (5) | −0.0040 (5) | 0.0047 (4) | 0.0005 (5) |
C2 | 0.0217 (5) | 0.0289 (6) | 0.0199 (5) | −0.0039 (5) | 0.0046 (4) | 0.0008 (5) |
C3 | 0.0277 (6) | 0.0405 (8) | 0.0185 (5) | −0.0055 (6) | 0.0043 (5) | 0.0013 (6) |
C4 | 0.0265 (6) | 0.0341 (8) | 0.0236 (6) | 0.0020 (6) | 0.0077 (5) | 0.0030 (6) |
C5 | 0.0369 (8) | 0.0312 (8) | 0.0220 (6) | 0.0065 (6) | 0.0108 (5) | 0.0009 (6) |
C6 | 0.0313 (6) | 0.0311 (7) | 0.0214 (5) | −0.0002 (6) | 0.0036 (5) | 0.0001 (6) |
C7 | 0.0284 (6) | 0.0264 (7) | 0.0262 (6) | 0.0050 (5) | 0.0052 (5) | 0.0026 (5) |
C8 | 0.0274 (6) | 0.0267 (6) | 0.0276 (6) | 0.0045 (6) | 0.0030 (5) | 0.0042 (6) |
N1 | 0.0219 (5) | 0.0354 (7) | 0.0213 (5) | −0.0016 (5) | 0.0033 (4) | −0.0009 (5) |
N2 | 0.0290 (6) | 0.0306 (7) | 0.0305 (7) | 0.0028 (5) | 0.0070 (5) | 0.0015 (5) |
O1 | 0.0323 (6) | 0.0503 (9) | 0.0396 (7) | 0.0109 (6) | 0.0124 (5) | 0.0149 (6) |
O2 | 0.0374 (7) | 0.0396 (7) | 0.0441 (7) | −0.0073 (6) | 0.0182 (6) | 0.0072 (6) |
O3 | 0.0525 (9) | 0.0407 (8) | 0.0450 (8) | 0.0155 (7) | 0.0281 (7) | 0.0151 (6) |
O4 | 0.0334 (6) | 0.0288 (5) | 0.0311 (6) | 0.0038 (5) | 0.0100 (5) | 0.0068 (5) |
Cl1 | 0.0458 (3) | 0.1072 (6) | 0.0373 (2) | 0.0320 (4) | −0.0088 (2) | 0.0035 (4) |
Cl2 | 0.0579 (4) | 0.0358 (3) | 0.1561 (10) | −0.0162 (3) | 0.0355 (5) | −0.0200 (4) |
Cl3 | 0.0682 (3) | 0.0438 (3) | 0.0360 (2) | 0.0260 (3) | 0.0218 (2) | 0.0057 (2) |
Geometric parameters (Å, º) top
C1—O1 | 1.249 (2) | C6—N2 | 1.484 (3) |
C1—O2 | 1.255 (2) | C6—H6A | 0.9700 |
C1—C2 | 1.537 (2) | C6—H6B | 0.9700 |
C2—N1 | 1.494 (2) | C7—O3 | 1.229 (2) |
C2—C3 | 1.527 (2) | C7—O4 | 1.250 (2) |
C2—H2 | 0.9800 | C7—C8 | 1.574 (2) |
C3—C4 | 1.523 (2) | C8—Cl1 | 1.7524 (16) |
C3—H3A | 0.9700 | C8—Cl2 | 1.7567 (19) |
C3—H3B | 0.9700 | C8—Cl3 | 1.7633 (16) |
C4—C5 | 1.531 (2) | N1—H1C | 0.850 (17) |
C4—H4A | 0.9700 | N1—H1A | 0.850 (7) |
C4—H4B | 0.9700 | N1—H1B | 0.850 (15) |
C5—C6 | 1.510 (2) | N2—H2A | 0.850 (12) |
C5—H5A | 0.9700 | N2—H2C | 0.850 (9) |
C5—H5B | 0.9700 | N2—H2B | 0.85 (3) |
| | | |
O1—C1—O2 | 125.68 (16) | N2—C6—C5 | 111.89 (14) |
O1—C1—C2 | 116.52 (15) | N2—C6—H6A | 109.2 |
O2—C1—C2 | 117.73 (17) | C5—C6—H6A | 109.2 |
N1—C2—C3 | 110.75 (13) | N2—C6—H6B | 109.2 |
N1—C2—C1 | 110.30 (13) | C5—C6—H6B | 109.2 |
C3—C2—C1 | 109.76 (12) | H6A—C6—H6B | 107.9 |
N1—C2—H2 | 108.7 | O3—C7—O4 | 128.21 (16) |
C3—C2—H2 | 108.7 | O3—C7—C8 | 115.16 (15) |
C1—C2—H2 | 108.7 | O4—C7—C8 | 116.63 (14) |
C4—C3—C2 | 113.74 (13) | C7—C8—Cl1 | 108.24 (12) |
C4—C3—H3A | 108.8 | C7—C8—Cl2 | 109.41 (11) |
C2—C3—H3A | 108.8 | Cl1—C8—Cl2 | 108.31 (10) |
C4—C3—H3B | 108.8 | C7—C8—Cl3 | 111.89 (11) |
C2—C3—H3B | 108.8 | Cl1—C8—Cl3 | 108.52 (9) |
H3A—C3—H3B | 107.7 | Cl2—C8—Cl3 | 110.39 (10) |
C3—C4—C5 | 113.40 (14) | C2—N1—H1C | 106.1 (18) |
C3—C4—H4A | 108.9 | C2—N1—H1A | 108 (2) |
C5—C4—H4A | 108.9 | H1C—N1—H1A | 114 (3) |
C3—C4—H4B | 108.9 | C2—N1—H1B | 108 (2) |
C5—C4—H4B | 108.9 | H1C—N1—H1B | 115 (3) |
H4A—C4—H4B | 107.7 | H1A—N1—H1B | 105 (3) |
C6—C5—C4 | 115.91 (13) | C6—N2—H2A | 110 (2) |
C6—C5—H5A | 108.3 | C6—N2—H2C | 99 (3) |
C4—C5—H5A | 108.3 | H2A—N2—H2C | 102 (3) |
C6—C5—H5B | 108.3 | C6—N2—H2B | 105 (3) |
C4—C5—H5B | 108.3 | H2A—N2—H2B | 108 (3) |
H5A—C5—H5B | 107.4 | H2C—N2—H2B | 131 (4) |
| | | |
O1—C1—C2—N1 | 163.35 (15) | C4—C5—C6—N2 | 60.74 (19) |
O2—C1—C2—N1 | −19.5 (2) | O3—C7—C8—Cl1 | 73.39 (19) |
O1—C1—C2—C3 | −74.4 (2) | O4—C7—C8—Cl1 | −106.63 (16) |
O2—C1—C2—C3 | 102.80 (18) | O3—C7—C8—Cl2 | −44.4 (2) |
N1—C2—C3—C4 | −65.54 (18) | O4—C7—C8—Cl2 | 135.55 (15) |
C1—C2—C3—C4 | 172.44 (15) | O3—C7—C8—Cl3 | −167.09 (15) |
C2—C3—C4—C5 | −175.78 (15) | O4—C7—C8—Cl3 | 12.9 (2) |
C3—C4—C5—C6 | 60.4 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O1i | 0.85 (2) | 2.01 (1) | 2.823 (2) | 161 (2) |
N1—H1A···O4ii | 0.85 (1) | 2.06 (1) | 2.9052 (18) | 173 (3) |
N1—H1A···Cl3ii | 0.85 (1) | 2.98 (3) | 3.4057 (16) | 113 (2) |
N1—H1B···O2iii | 0.85 (2) | 2.31 (2) | 3.086 (2) | 151 (3) |
N1—H1B···O1iii | 0.85 (2) | 2.59 (2) | 3.361 (2) | 152 (3) |
N2—H2A···O2ii | 0.85 (1) | 2.05 (1) | 2.894 (2) | 173 (3) |
N2—H2C···O4iv | 0.85 (1) | 2.12 (2) | 2.881 (2) | 149 (4) |
N2—H2B···O3v | 0.85 (3) | 1.91 (3) | 2.756 (2) | 173 (4) |
N2—H2B···O4v | 0.85 (3) | 2.60 (3) | 3.084 (2) | 118 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x+1, y+1/2, −z; (iii) x+1, y, z; (iv) x+1, y+1, z; (v) x, y+1, z. |