N-Ethyl­ethanaminium 3,5,6-trichloro­pyridin-2-olate

In the title salt, C₄H₁₂N⁺·C₅HCl₃NO⁻, 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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.116
• Data-to-parameter ratio = 21.6

checkCIF/PLATON results

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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

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Computing details

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

Crystal data

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) Å^3	0.38 × 0.36 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2106 reflections with F^2 > 2σ(F^2)
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

Refinement on F^2	w = 1/[0.0011Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max < 0.001
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1^i	0.90	1.87	2.748 (2)	166

Symmetry code: (i) −x, −y, −z+1.