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In the title salt, C
4H
12N
+·C
5HCl
3NO
−, the non-H atoms of the cation are essentially coplanar. Intermolecular N—H
O hydrogen bonds link two cations and two anions into a centrosymmetric cluster. The crystal packing is further stabilized by van der Waals forces.
Supporting information
CCDC reference: 605027
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.116
- Data-to-parameter ratio = 21.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
N-Ethylethanaminium 3,5,6-trichloropyridin-2-olate
top
Crystal data top
C4H12N+·C5HCl3NO− | Z = 2 |
Mr = 271.57 | F(000) = 280.00 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
Hall symbol: -P 1 | Melting point: 127 K |
a = 7.527 (6) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 9.196 (6) Å | Cell parameters from 5373 reflections |
c = 10.978 (7) Å | θ = 3.0–27.5° |
α = 106.36 (2)° | µ = 0.68 mm−1 |
β = 105.32 (3)° | T = 298 K |
γ = 105.28 (3)° | Chunk, colourless |
V = 654.6 (8) Å3 | 0.38 × 0.36 × 0.28 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2106 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.023 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −9→9 |
Tmin = 0.761, Tmax = 0.827 | k = −11→10 |
6442 measured reflections | l = −14→14 |
2964 independent reflections | |
Refinement top
Refinement on F2 | w = 1/[0.0011Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.039 | (Δ/σ)max < 0.001 |
wR(F2) = 0.116 | Δρmax = 0.50 e Å−3 |
S = 1.01 | Δρmin = −0.42 e Å−3 |
2964 reflections | Extinction correction: Larson (1970) |
137 parameters | Extinction coefficient: 42 (12) |
H-atom parameters constrained | |
Special details top
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and
goodness of fit (S) are based on F2. R-factor (gt) are
based on F. The threshold expression of F2 > 2.0
σ(F2) is used only for calculating R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.53393 (10) | 0.42409 (6) | 0.63185 (6) | 0.07760 (18) | |
Cl2 | 0.85021 (8) | 0.48780 (6) | 1.15486 (5) | 0.07117 (16) | |
Cl3 | 0.46815 (9) | 0.18795 (6) | 1.09429 (5) | 0.07312 (18) | |
O1 | 0.2181 (2) | 0.14912 (14) | 0.62784 (12) | 0.0599 (3) | |
N1 | 0.3529 (2) | 0.17987 (17) | 0.84727 (14) | 0.0480 (3) | |
N2 | 0.0532 (2) | 0.11234 (17) | 0.36530 (13) | 0.0481 (3) | |
C1 | 0.3593 (2) | 0.2274 (2) | 0.74258 (17) | 0.0447 (4) | |
C2 | 0.5260 (2) | 0.3628 (2) | 0.76596 (18) | 0.0469 (4) | |
C3 | 0.6741 (2) | 0.4423 (2) | 0.89062 (19) | 0.0506 (4) | |
C4 | 0.6627 (2) | 0.3890 (2) | 0.99530 (17) | 0.0473 (4) | |
C5 | 0.4975 (2) | 0.2588 (2) | 0.96741 (17) | 0.0456 (4) | |
C6 | −0.1467 (4) | 0.2672 (2) | 0.4361 (2) | 0.0817 (8) | |
C7 | −0.0379 (3) | 0.2317 (2) | 0.3432 (2) | 0.0640 (6) | |
C8 | 0.1583 (3) | 0.0729 (2) | 0.2730 (2) | 0.0694 (6) | |
C9 | 0.2469 (4) | −0.0480 (3) | 0.2959 (3) | 0.0983 (11) | |
H31 | 0.7819 | 0.5317 | 0.9055 | 0.059* | |
H61 | −0.2408 | 0.1670 | 0.4263 | 0.103* | |
H62 | −0.2148 | 0.3362 | 0.4133 | 0.103* | |
H63 | −0.0546 | 0.3210 | 0.5287 | 0.103* | |
H71 | 0.0646 | 0.3319 | 0.3587 | 0.079* | |
H72 | −0.1286 | 0.1891 | 0.2494 | 0.080* | |
H81 | 0.2620 | 0.1716 | 0.2872 | 0.088* | |
H82 | 0.0668 | 0.0299 | 0.1793 | 0.088* | |
H91 | 0.3252 | −0.0625 | 0.2404 | 0.132* | |
H92 | 0.1435 | −0.1500 | 0.2716 | 0.132* | |
H93 | 0.3294 | −0.0097 | 0.3902 | 0.132* | |
H201 | 0.1385 | 0.1529 | 0.4521 | 0.056* | |
H202 | −0.0420 | 0.0204 | 0.3528 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0882 (4) | 0.0778 (3) | 0.0631 (3) | 0.0067 (2) | 0.0315 (2) | 0.0399 (2) |
Cl2 | 0.0570 (3) | 0.0762 (3) | 0.0555 (2) | 0.0187 (2) | −0.0001 (2) | 0.0142 (2) |
Cl3 | 0.0862 (4) | 0.0862 (4) | 0.0543 (2) | 0.0260 (3) | 0.0272 (2) | 0.0405 (2) |
O1 | 0.0582 (7) | 0.0578 (7) | 0.0431 (6) | 0.0007 (6) | 0.0059 (5) | 0.0208 (5) |
N1 | 0.0468 (8) | 0.0484 (7) | 0.0470 (7) | 0.0115 (6) | 0.0161 (6) | 0.0219 (6) |
N2 | 0.0475 (8) | 0.0485 (7) | 0.0442 (7) | 0.0081 (6) | 0.0147 (6) | 0.0223 (6) |
C1 | 0.0440 (9) | 0.0444 (8) | 0.0451 (8) | 0.0137 (7) | 0.0163 (7) | 0.0186 (7) |
C2 | 0.0514 (10) | 0.0472 (9) | 0.0469 (8) | 0.0159 (7) | 0.0222 (7) | 0.0224 (7) |
C3 | 0.0407 (9) | 0.0459 (9) | 0.0594 (10) | 0.0096 (7) | 0.0191 (8) | 0.0167 (8) |
C4 | 0.0424 (9) | 0.0504 (9) | 0.0440 (8) | 0.0191 (7) | 0.0115 (7) | 0.0125 (7) |
C5 | 0.0505 (9) | 0.0503 (9) | 0.0437 (8) | 0.0228 (7) | 0.0198 (7) | 0.0221 (7) |
C6 | 0.0840 (17) | 0.0806 (15) | 0.0936 (17) | 0.0433 (14) | 0.0371 (15) | 0.0349 (13) |
C7 | 0.0668 (12) | 0.0653 (12) | 0.0671 (12) | 0.0243 (10) | 0.0197 (10) | 0.0393 (10) |
C8 | 0.0773 (15) | 0.0759 (13) | 0.0669 (12) | 0.0252 (11) | 0.0428 (12) | 0.0309 (10) |
C9 | 0.106 (2) | 0.0965 (18) | 0.128 (2) | 0.0508 (17) | 0.072 (2) | 0.0509 (18) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.728 (2) | N2—H201 | 0.900 |
Cl2—C4 | 1.7342 (15) | N2—H202 | 0.900 |
Cl3—C5 | 1.735 (2) | C3—H31 | 0.930 |
O1—C1 | 1.2699 (17) | C6—H61 | 0.960 |
N1—C1 | 1.347 (2) | C6—H62 | 0.960 |
N1—C5 | 1.3181 (19) | C6—H63 | 0.960 |
N2—C7 | 1.480 (3) | C7—H71 | 0.970 |
N2—C8 | 1.467 (3) | C7—H72 | 0.970 |
C1—C2 | 1.421 (2) | C8—H81 | 0.970 |
C2—C3 | 1.360 (2) | C8—H82 | 0.970 |
C3—C4 | 1.384 (3) | C9—H91 | 0.960 |
C4—C5 | 1.371 (2) | C9—H92 | 0.960 |
C6—C7 | 1.487 (4) | C9—H93 | 0.960 |
C8—C9 | 1.484 (4) | | |
| | | |
Cl1···Cl1 | 3.5302 (10) | H31···Cl2 | 3.050 |
Cl2···C1 | 3.474 (2) | H31···Cl3 | 3.570 |
Cl3···C8 | 3.563 (3) | H31···C5 | 3.501 |
O1···O1 | 3.4970 (14) | H61···O1 | 2.860 |
O1···N2 | 2.7022 (19) | H61···N1 | 3.429 |
O1···N2 | 2.748 (2) | H61···C1 | 3.320 |
O1···C6 | 3.599 (3) | H61···C9 | 3.506 |
O1···C6 | 3.555 (3) | H61···C9 | 3.526 |
O1···C7 | 3.544 (2) | H61···H91 | 3.116 |
N1···N2 | 3.2213 (16) | H61···H92 | 3.261 |
N1···C7 | 3.537 (2) | H61···H93 | 3.075 |
N1···C8 | 3.581 (2) | H61···H93 | 2.904 |
N2···O1 | 2.7022 (19) | H62···Cl1 | 3.478 |
N2···O1 | 2.748 (2) | H62···Cl2 | 3.583 |
N2···N1 | 3.2213 (16) | H62···Cl3 | 3.316 |
N2···C1 | 3.415 (2) | H62···C6 | 3.527 |
C1···Cl2 | 3.474 (2) | H62···H62 | 3.397 |
C1···N2 | 3.415 (2) | H62···H63 | 3.045 |
C3···C5 | 3.489 (2) | H62···H71 | 3.040 |
C4···C4 | 3.582 (3) | H62···H81 | 3.537 |
C5···C3 | 3.489 (2) | H63···Cl2 | 3.136 |
C6···O1 | 3.599 (3) | H63···O1 | 3.066 |
C6···O1 | 3.555 (3) | H63···C6 | 3.554 |
C7···O1 | 3.544 (2) | H63···H62 | 3.045 |
C7···N1 | 3.537 (2) | H63···H63 | 3.453 |
C8···Cl3 | 3.563 (3) | H63···H71 | 3.110 |
C8···N1 | 3.581 (2) | H63···H92 | 3.146 |
Cl1···H62 | 3.478 | H63···H93 | 3.543 |
Cl1···H71 | 3.210 | H71···Cl1 | 3.210 |
Cl1···H81 | 3.515 | H71···Cl2 | 3.284 |
Cl1···H81 | 3.374 | H71···C6 | 3.526 |
Cl1···H201 | 3.031 | H71···H62 | 3.040 |
Cl2···H31 | 3.050 | H71···H63 | 3.110 |
Cl2···H62 | 3.583 | H72···Cl2 | 3.224 |
Cl2···H63 | 3.136 | H72···Cl3 | 3.058 |
Cl2···H71 | 3.284 | H72···N1 | 3.082 |
Cl2···H72 | 3.224 | H81···Cl1 | 3.515 |
Cl2···H92 | 3.136 | H81···Cl1 | 3.374 |
Cl3···H31 | 3.570 | H81···Cl3 | 2.951 |
Cl3···H62 | 3.316 | H81···H62 | 3.537 |
Cl3···H72 | 3.058 | H82···Cl3 | 3.471 |
Cl3···H81 | 2.951 | H82···N1 | 3.126 |
Cl3···H82 | 3.471 | H91···Cl3 | 3.274 |
Cl3···H91 | 3.274 | H91···N1 | 3.160 |
O1···H61 | 2.860 | H91···C1 | 3.130 |
O1···H63 | 3.066 | H91···C2 | 3.233 |
O1···H92 | 3.197 | H91···C3 | 3.384 |
O1···H93 | 3.048 | H91···C4 | 3.407 |
O1···H201 | 1.876 | H91···C5 | 3.286 |
O1···H201 | 3.023 | H91···H61 | 3.116 |
O1···H202 | 2.828 | H92···Cl2 | 3.136 |
O1···H202 | 1.865 | H92···O1 | 3.197 |
N1···H61 | 3.429 | H92···N1 | 3.524 |
N1···H72 | 3.082 | H92···C2 | 3.583 |
N1···H82 | 3.126 | H92···C3 | 3.580 |
N1···H91 | 3.160 | H92···H61 | 3.261 |
N1···H92 | 3.524 | H92···H63 | 3.146 |
N1···H202 | 2.535 | H93···O1 | 3.048 |
C1···H61 | 3.320 | H93···H61 | 3.075 |
C1···H91 | 3.130 | H93···H61 | 2.904 |
C1···H201 | 2.961 | H93···H63 | 3.543 |
C1···H202 | 2.541 | H93···H93 | 2.946 |
C2···H91 | 3.233 | H201···Cl1 | 3.031 |
C2···H92 | 3.583 | H201···O1 | 1.876 |
C2···H201 | 3.476 | H201···O1 | 3.023 |
C3···H91 | 3.384 | H201···C1 | 2.961 |
C3···H92 | 3.580 | H201···C2 | 3.476 |
C4···H91 | 3.407 | H201···H202 | 3.129 |
C5···H31 | 3.501 | H202···O1 | 2.828 |
C5···H91 | 3.286 | H202···O1 | 1.865 |
C6···H62 | 3.527 | H202···N1 | 2.535 |
C6···H63 | 3.554 | H202···C1 | 2.541 |
C6···H71 | 3.526 | H202···H201 | 3.129 |
C9···H61 | 3.506 | H202···H202 | 3.274 |
C9···H61 | 3.526 | | |
| | | |
C1—N1—C5 | 120.24 (15) | C4—C3—H31 | 120.3 |
C7—N2—C8 | 112.56 (19) | C7—C6—H61 | 109.4 |
O1—C1—N1 | 118.98 (15) | C7—C6—H62 | 109.5 |
O1—C1—C2 | 123.00 (18) | C7—C6—H63 | 109.5 |
N1—C1—C2 | 118.02 (13) | H61—C6—H62 | 109.5 |
Cl1—C2—C1 | 118.02 (12) | H61—C6—H63 | 109.5 |
Cl1—C2—C3 | 121.17 (15) | H62—C6—H63 | 109.5 |
C1—C2—C3 | 120.81 (19) | N2—C7—H71 | 109.3 |
C2—C3—C4 | 119.41 (16) | N2—C7—H72 | 109.4 |
Cl2—C4—C3 | 120.21 (12) | C6—C7—H71 | 109.3 |
Cl2—C4—C5 | 122.50 (16) | C6—C7—H72 | 109.3 |
C3—C4—C5 | 117.28 (14) | H71—C7—H72 | 108.0 |
Cl3—C5—N1 | 115.54 (14) | N2—C8—H81 | 109.2 |
Cl3—C5—C4 | 120.24 (12) | N2—C8—H82 | 109.3 |
N1—C5—C4 | 124.22 (19) | C9—C8—H81 | 109.2 |
N2—C7—C6 | 111.5 (2) | C9—C8—H82 | 109.4 |
N2—C8—C9 | 111.7 (2) | H81—C8—H82 | 107.9 |
C7—N2—H201 | 109.1 | C8—C9—H91 | 109.3 |
C7—N2—H202 | 109.1 | C8—C9—H92 | 109.5 |
C8—N2—H201 | 109.1 | C8—C9—H93 | 109.6 |
C8—N2—H202 | 109.0 | H91—C9—H92 | 109.5 |
H201—N2—H202 | 107.8 | H91—C9—H93 | 109.5 |
C2—C3—H31 | 120.3 | H92—C9—H93 | 109.5 |
| | | |
C1—N1—C5—Cl3 | 178.59 (16) | N1—C1—C2—C3 | −0.2 (3) |
C1—N1—C5—C4 | −1.2 (3) | Cl1—C2—C3—C4 | −179.71 (17) |
C5—N1—C1—O1 | 179.93 (19) | C1—C2—C3—C4 | 0.7 (3) |
C5—N1—C1—C2 | 0.5 (3) | C2—C3—C4—Cl2 | 179.72 (17) |
C7—N2—C8—C9 | −179.50 (15) | C2—C3—C4—C5 | −1.4 (3) |
C8—N2—C7—C6 | 178.90 (14) | Cl2—C4—C5—Cl3 | 0.7 (2) |
O1—C1—C2—Cl1 | 0.7 (2) | Cl2—C4—C5—N1 | −179.44 (17) |
O1—C1—C2—C3 | −179.7 (2) | C3—C4—C5—Cl3 | −178.14 (16) |
N1—C1—C2—Cl1 | −179.82 (15) | C3—C4—C5—N1 | 1.7 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H201···O1 | 0.90 | 1.88 | 2.7022 (19) | 152 |
N2—H202···O1i | 0.90 | 1.87 | 2.748 (2) | 166 |
Symmetry code: (i) −x, −y, −z+1. |
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