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The title compound C6H15N2O2+·C2Cl3O2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807010021/su2004sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807010021/su2004Isup2.hkl
Contains datablock I

CCDC reference: 633206

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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+·C2Cl3O2F(000) = 320
Mr = 309.57Dx = 1.601 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 6860 reflections
a = 5.7283 (2) Åθ = 2.6–33.0°
b = 9.0412 (3) ŵ = 0.72 mm1
c = 12.4994 (4) ÅT = 293 K
β = 97.251 (1)°Needle, colourless
V = 642.18 (4) Å30.3 × 0.2 × 0.2 mm
Z = 2
Data collection top
Bruker APEXII
diffractometer
4946 independent reflections
Radiation source: fine-focus sealed tube4625 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω and φ scansθmax = 34.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
h = 99
Tmin = 0.81, Tmax = 0.91k = 1414
10511 measured reflectionsl = 1915
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H 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 reflectionsΔρmax = 0.90 e Å3
178 parametersΔρmin = 0.52 e Å3
7 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
C10.3866 (3)1.0223 (2)0.04870 (12)0.0261 (3)
C20.6303 (2)1.03418 (18)0.01008 (11)0.0233 (2)
H20.69791.13090.03140.028*
C30.6056 (3)1.0223 (2)0.11266 (12)0.0288 (3)
H3A0.55140.92360.13370.035*
H3B0.48651.09180.14330.035*
C40.8330 (3)1.0529 (2)0.16001 (13)0.0277 (3)
H4A0.94870.97880.13370.033*
H4B0.89361.14860.13470.033*
C50.8027 (3)1.0519 (2)0.28351 (13)0.0294 (3)
H5A0.95561.06810.30710.035*
H5B0.74980.95430.30800.035*
C60.6333 (3)1.1647 (2)0.33822 (12)0.0279 (3)
H6A0.62341.15260.41580.034*
H6B0.47801.14740.31760.034*
C70.2409 (3)0.50713 (19)0.35804 (13)0.0269 (3)
C80.1016 (3)0.6569 (2)0.35497 (12)0.0273 (3)
N10.7901 (2)0.91643 (17)0.06129 (11)0.0262 (2)
N20.7075 (3)1.31828 (19)0.30912 (13)0.0298 (3)
O10.2558 (3)1.1327 (2)0.03332 (13)0.0401 (3)
O20.3325 (3)0.90158 (19)0.08859 (13)0.0392 (3)
O30.3841 (3)0.5030 (2)0.42340 (14)0.0442 (4)
O40.1931 (2)0.40808 (16)0.29448 (11)0.0306 (2)
Cl10.10432 (12)0.66655 (12)0.47101 (5)0.0646 (2)
Cl20.29770 (15)0.80593 (9)0.35709 (11)0.0814 (3)
Cl30.04997 (12)0.66829 (6)0.24091 (4)0.04799 (15)
H1C0.743 (4)0.8358 (15)0.031 (2)0.025 (6)*
H1A0.783 (5)0.917 (4)0.1288 (4)0.034 (7)*
H1B0.9309 (19)0.940 (4)0.054 (3)0.040 (7)*
H2A0.691 (5)1.335 (3)0.2436 (7)0.031 (6)*
H2C0.8557 (10)1.308 (5)0.306 (3)0.054 (9)*
H2B0.612 (5)1.373 (4)0.349 (3)0.054 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0215 (5)0.0373 (8)0.0200 (5)0.0040 (5)0.0047 (4)0.0005 (5)
C20.0217 (5)0.0289 (6)0.0199 (5)0.0039 (5)0.0046 (4)0.0008 (5)
C30.0277 (6)0.0405 (8)0.0185 (5)0.0055 (6)0.0043 (5)0.0013 (6)
C40.0265 (6)0.0341 (8)0.0236 (6)0.0020 (6)0.0077 (5)0.0030 (6)
C50.0369 (8)0.0312 (8)0.0220 (6)0.0065 (6)0.0108 (5)0.0009 (6)
C60.0313 (6)0.0311 (7)0.0214 (5)0.0002 (6)0.0036 (5)0.0001 (6)
C70.0284 (6)0.0264 (7)0.0262 (6)0.0050 (5)0.0052 (5)0.0026 (5)
C80.0274 (6)0.0267 (6)0.0276 (6)0.0045 (6)0.0030 (5)0.0042 (6)
N10.0219 (5)0.0354 (7)0.0213 (5)0.0016 (5)0.0033 (4)0.0009 (5)
N20.0290 (6)0.0306 (7)0.0305 (7)0.0028 (5)0.0070 (5)0.0015 (5)
O10.0323 (6)0.0503 (9)0.0396 (7)0.0109 (6)0.0124 (5)0.0149 (6)
O20.0374 (7)0.0396 (7)0.0441 (7)0.0073 (6)0.0182 (6)0.0072 (6)
O30.0525 (9)0.0407 (8)0.0450 (8)0.0155 (7)0.0281 (7)0.0151 (6)
O40.0334 (6)0.0288 (5)0.0311 (6)0.0038 (5)0.0100 (5)0.0068 (5)
Cl10.0458 (3)0.1072 (6)0.0373 (2)0.0320 (4)0.0088 (2)0.0035 (4)
Cl20.0579 (4)0.0358 (3)0.1561 (10)0.0162 (3)0.0355 (5)0.0200 (4)
Cl30.0682 (3)0.0438 (3)0.0360 (2)0.0260 (3)0.0218 (2)0.0057 (2)
Geometric parameters (Å, º) top
C1—O11.249 (2)C6—N21.484 (3)
C1—O21.255 (2)C6—H6A0.9700
C1—C21.537 (2)C6—H6B0.9700
C2—N11.494 (2)C7—O31.229 (2)
C2—C31.527 (2)C7—O41.250 (2)
C2—H20.9800C7—C81.574 (2)
C3—C41.523 (2)C8—Cl11.7524 (16)
C3—H3A0.9700C8—Cl21.7567 (19)
C3—H3B0.9700C8—Cl31.7633 (16)
C4—C51.531 (2)N1—H1C0.850 (17)
C4—H4A0.9700N1—H1A0.850 (7)
C4—H4B0.9700N1—H1B0.850 (15)
C5—C61.510 (2)N2—H2A0.850 (12)
C5—H5A0.9700N2—H2C0.850 (9)
C5—H5B0.9700N2—H2B0.85 (3)
O1—C1—O2125.68 (16)N2—C6—C5111.89 (14)
O1—C1—C2116.52 (15)N2—C6—H6A109.2
O2—C1—C2117.73 (17)C5—C6—H6A109.2
N1—C2—C3110.75 (13)N2—C6—H6B109.2
N1—C2—C1110.30 (13)C5—C6—H6B109.2
C3—C2—C1109.76 (12)H6A—C6—H6B107.9
N1—C2—H2108.7O3—C7—O4128.21 (16)
C3—C2—H2108.7O3—C7—C8115.16 (15)
C1—C2—H2108.7O4—C7—C8116.63 (14)
C4—C3—C2113.74 (13)C7—C8—Cl1108.24 (12)
C4—C3—H3A108.8C7—C8—Cl2109.41 (11)
C2—C3—H3A108.8Cl1—C8—Cl2108.31 (10)
C4—C3—H3B108.8C7—C8—Cl3111.89 (11)
C2—C3—H3B108.8Cl1—C8—Cl3108.52 (9)
H3A—C3—H3B107.7Cl2—C8—Cl3110.39 (10)
C3—C4—C5113.40 (14)C2—N1—H1C106.1 (18)
C3—C4—H4A108.9C2—N1—H1A108 (2)
C5—C4—H4A108.9H1C—N1—H1A114 (3)
C3—C4—H4B108.9C2—N1—H1B108 (2)
C5—C4—H4B108.9H1C—N1—H1B115 (3)
H4A—C4—H4B107.7H1A—N1—H1B105 (3)
C6—C5—C4115.91 (13)C6—N2—H2A110 (2)
C6—C5—H5A108.3C6—N2—H2C99 (3)
C4—C5—H5A108.3H2A—N2—H2C102 (3)
C6—C5—H5B108.3C6—N2—H2B105 (3)
C4—C5—H5B108.3H2A—N2—H2B108 (3)
H5A—C5—H5B107.4H2C—N2—H2B131 (4)
O1—C1—C2—N1163.35 (15)C4—C5—C6—N260.74 (19)
O2—C1—C2—N119.5 (2)O3—C7—C8—Cl173.39 (19)
O1—C1—C2—C374.4 (2)O4—C7—C8—Cl1106.63 (16)
O2—C1—C2—C3102.80 (18)O3—C7—C8—Cl244.4 (2)
N1—C2—C3—C465.54 (18)O4—C7—C8—Cl2135.55 (15)
C1—C2—C3—C4172.44 (15)O3—C7—C8—Cl3167.09 (15)
C2—C3—C4—C5175.78 (15)O4—C7—C8—Cl312.9 (2)
C3—C4—C5—C660.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O1i0.85 (2)2.01 (1)2.823 (2)161 (2)
N1—H1A···O4ii0.85 (1)2.06 (1)2.9052 (18)173 (3)
N1—H1A···Cl3ii0.85 (1)2.98 (3)3.4057 (16)113 (2)
N1—H1B···O2iii0.85 (2)2.31 (2)3.086 (2)151 (3)
N1—H1B···O1iii0.85 (2)2.59 (2)3.361 (2)152 (3)
N2—H2A···O2ii0.85 (1)2.05 (1)2.894 (2)173 (3)
N2—H2C···O4iv0.85 (1)2.12 (2)2.881 (2)149 (4)
N2—H2B···O3v0.85 (3)1.91 (3)2.756 (2)173 (4)
N2—H2B···O4v0.85 (3)2.60 (3)3.084 (2)118 (3)
Symmetry codes: (i) x+1, y1/2, z; (ii) x+1, y+1/2, z; (iii) x+1, y, z; (iv) x+1, y+1, z; (v) x, y+1, z.
 

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