4-Carbamoylpyridin-1-ium 2,2,2-trichloro-acetate.

In the asymmetric unit of the title salt, C(6)H(7)N(2)O(+)·C(2)Cl(3)O(2) (-), there are two crystallographic independent ion pairs. The amide groups of the 4-carbamoylpyridin-1-ium ions are slightly twisted out of the plane of the aromatic ring with C-C-C-N torsion angles of 8.8 (9)° and 4.6 (8)°. In the crystal, the 4-carbamoylpyridin-1-ium ion is N-H⋯O hydrogen bonded to the trichloro-acetate ion via the pyridinium unit and amide group. Layers parallel to the ac plane are formed due to the N-H⋯O hydrogen bonding of the adjacent amide groups of 4-carbamoylpyridin-1-ium ions. Weak C-H⋯O inter-actions also occur.

Related literature

For applications of co-crystals, see: Karki et al. (2009 ▶); Friščić & Jones (2010 ▶). For related structures, see: Das & Baruah (2011 ▶).

Experimental

Crystal data

C6H7N2O+·C2Cl3O2 −

M = 285.51

Monoclinic,

a = 9.8768 (3) Å

b = 9.4403 (3) Å

c = 12.5157 (3) Å

β = 90.240 (2)°

V = 1166.95 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.78 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.860, T max = 0.860

11114 measured reflections

5195 independent reflections

4452 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.199

S = 1.04

5195 reflections

289 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 2512 Friedel pairs

Flack parameter: 0.08 (12)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536812035507/bq2374sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035507/bq2374Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035507/bq2374Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H7N2O+·C2Cl3O2−	F(000) = 576
Mr = 285.51	Dx = 1.625 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 4989 reflections
a = 9.8768 (3) Å	θ = 3.0–30.3°
b = 9.4403 (3) Å	µ = 0.78 mm−1
c = 12.5157 (3) Å	T = 293 K
β = 90.240 (2)°	Cube, colourless
V = 1166.95 (6) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	5195 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4452 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
Detector resolution: 10.4933 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −12→12
Tmin = 0.860, Tmax = 0.860	l = −16→16
11114 measured reflections

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)] = 0.069	H-atom parameters constrained
wR(F2) = 0.199	w = 1/[σ2(Fo2) + (0.104P)2 + 1.1455P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5195 reflections	Δρmax = 0.53 e Å−3
289 parameters	Δρmin = −0.47 e Å−3
2 restraints	Absolute structure: Flack (1983), 2512 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.08 (12)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.

	x	y	z	Uiso*/Ueq
Cl1	0.10761 (17)	0.0588 (2)	0.78518 (16)	0.0826 (5)
Cl2	−0.0364 (2)	0.03005 (15)	0.98391 (14)	0.0768 (5)
Cl3	−0.18351 (17)	0.0792 (2)	0.78632 (16)	0.0819 (5)
Cl4	0.3217 (3)	0.0487 (2)	0.5048 (3)	0.1287 (12)
Cl5	0.4613 (3)	0.04358 (18)	0.70263 (17)	0.0950 (7)
Cl6	0.6112 (3)	0.0464 (2)	0.5097 (3)	0.1206 (10)
N1	0.9738 (5)	0.3469 (4)	0.5899 (3)	0.0465 (9)
H1A	0.9911	0.3487	0.6573	0.07*
N2	0.9725 (5)	0.3126 (5)	0.1897 (3)	0.0545 (11)
H2A	0.9523	0.3112	0.1228	0.082*
H2B	1.0545	0.2975	0.21	0.082*
N3	0.4737 (5)	0.6594 (5)	0.3579 (3)	0.0489 (10)
H3A	0.4908	0.6608	0.2906	0.073*
N4	0.4753 (5)	0.6746 (5)	0.7577 (3)	0.0519 (10)
H4A	0.4549	0.6785	0.8243	0.078*
H4B	0.5587	0.6786	0.7384	0.078*
O1	−0.0643 (6)	0.3280 (4)	0.9614 (3)	0.0789 (15)
O2	0.0158 (5)	0.3511 (5)	0.7986 (3)	0.0713 (13)
O3	0.5208 (6)	0.3362 (5)	0.6487 (3)	0.0713 (12)
O4	0.4394 (7)	0.3324 (4)	0.4841 (3)	0.0834 (16)
O5	0.7614 (5)	0.3595 (9)	0.2357 (4)	0.116 (3)
O6	0.2588 (5)	0.6567 (10)	0.7106 (4)	0.138 (3)
C1	1.0769 (5)	0.3404 (6)	0.5206 (4)	0.0512 (12)
H1	1.1657	0.3372	0.5456	0.061*
C2	1.0507 (5)	0.3384 (6)	0.4112 (4)	0.0451 (10)
H2	1.1213	0.3352	0.3623	0.054*
C3	0.9178 (5)	0.3415 (5)	0.3768 (4)	0.0410 (9)
C4	0.8152 (5)	0.3479 (5)	0.4506 (4)	0.0471 (10)
H4	0.7253	0.3503	0.4283	0.057*
C5	0.8467 (6)	0.3506 (6)	0.5575 (4)	0.0555 (13)
H5	0.7775	0.3551	0.6076	0.067*
C6	0.8784 (6)	0.3376 (6)	0.2605 (4)	0.0538 (13)
C7	0.5779 (6)	0.6614 (6)	0.4269 (4)	0.0519 (12)
H7	0.6667	0.6613	0.4026	0.062*
C8	0.5502 (5)	0.6637 (5)	0.5346 (4)	0.0470 (11)
H8	0.6208	0.6664	0.5839	0.056*
C9	0.4176 (5)	0.6621 (5)	0.5696 (4)	0.0418 (10)
C10	0.3170 (6)	0.6561 (6)	0.4940 (4)	0.0543 (12)
H10	0.2271	0.6525	0.5155	0.065*
C11	0.3464 (6)	0.6552 (6)	0.3887 (4)	0.0556 (13)
H11	0.2771	0.6518	0.3382	0.067*
C12	0.3792 (5)	0.6626 (7)	0.6854 (4)	0.0558 (13)
C13	−0.0250 (5)	0.2831 (5)	0.8761 (3)	0.0436 (10)
C14	−0.0344 (5)	0.1177 (5)	0.8593 (4)	0.0481 (10)
C15	0.4722 (5)	0.2781 (5)	0.5682 (3)	0.0419 (9)
C16	0.4658 (5)	0.1124 (5)	0.5706 (4)	0.0463 (10)

	U11	U22	U33	U12	U13	U23
Cl1	0.0647 (9)	0.0950 (12)	0.0882 (12)	0.0167 (8)	0.0213 (8)	−0.0217 (10)
Cl2	0.1036 (12)	0.0537 (7)	0.0730 (10)	0.0026 (8)	0.0071 (9)	0.0188 (7)
Cl3	0.0599 (8)	0.1001 (12)	0.0856 (11)	−0.0164 (8)	−0.0161 (7)	−0.0240 (10)
Cl4	0.1135 (16)	0.0708 (11)	0.201 (3)	−0.0082 (11)	−0.0941 (19)	−0.0250 (14)
Cl5	0.1471 (19)	0.0620 (9)	0.0760 (11)	−0.0091 (10)	0.0003 (12)	0.0210 (8)
Cl6	0.1032 (15)	0.0709 (12)	0.188 (3)	0.0098 (11)	0.0773 (17)	−0.0256 (14)
N1	0.066 (3)	0.049 (2)	0.0250 (16)	−0.0007 (19)	0.0018 (17)	0.0029 (14)
N2	0.059 (2)	0.083 (3)	0.0216 (17)	0.008 (2)	−0.0014 (16)	−0.0018 (19)
N3	0.065 (3)	0.053 (2)	0.0280 (18)	0.004 (2)	−0.0005 (17)	0.0013 (16)
N4	0.057 (2)	0.069 (3)	0.0296 (19)	0.003 (2)	−0.0002 (17)	−0.0002 (18)
O1	0.146 (5)	0.059 (2)	0.0319 (18)	0.012 (3)	0.008 (2)	0.0011 (16)
O2	0.116 (4)	0.071 (3)	0.0270 (16)	−0.017 (2)	0.002 (2)	0.0035 (16)
O3	0.117 (4)	0.065 (2)	0.0324 (18)	−0.017 (2)	0.004 (2)	−0.0052 (16)
O4	0.158 (5)	0.052 (2)	0.040 (2)	0.007 (3)	−0.014 (3)	0.0037 (17)
O5	0.049 (2)	0.251 (8)	0.047 (2)	0.012 (4)	−0.0102 (19)	0.015 (4)
O6	0.051 (3)	0.312 (11)	0.051 (3)	−0.018 (4)	0.011 (2)	0.008 (4)
C1	0.047 (2)	0.067 (3)	0.039 (2)	0.005 (2)	−0.005 (2)	0.001 (2)
C2	0.040 (2)	0.065 (3)	0.030 (2)	0.003 (2)	0.0028 (17)	0.0013 (19)
C3	0.043 (2)	0.052 (3)	0.0288 (18)	−0.0013 (19)	0.0020 (16)	0.0073 (16)
C4	0.040 (2)	0.057 (3)	0.044 (2)	0.001 (2)	0.0088 (19)	0.003 (2)
C5	0.061 (3)	0.065 (3)	0.041 (3)	0.000 (2)	0.018 (2)	0.004 (2)
C6	0.051 (3)	0.082 (4)	0.029 (2)	−0.007 (3)	−0.0046 (19)	0.010 (2)
C7	0.053 (3)	0.063 (3)	0.040 (2)	−0.008 (2)	0.010 (2)	0.004 (2)
C8	0.049 (3)	0.063 (3)	0.029 (2)	−0.008 (2)	−0.0054 (19)	0.0021 (19)
C9	0.047 (2)	0.051 (3)	0.0277 (19)	−0.0028 (19)	−0.0021 (17)	0.0005 (17)
C10	0.049 (3)	0.071 (3)	0.043 (2)	0.002 (2)	−0.005 (2)	−0.001 (2)
C11	0.056 (3)	0.065 (3)	0.046 (3)	0.012 (3)	−0.010 (2)	−0.001 (2)
C12	0.044 (2)	0.093 (4)	0.030 (2)	−0.004 (3)	0.0067 (19)	0.003 (2)
C13	0.056 (2)	0.046 (2)	0.028 (2)	−0.001 (2)	−0.0072 (18)	0.0027 (17)
C14	0.047 (2)	0.051 (3)	0.046 (2)	−0.002 (2)	0.0039 (19)	−0.006 (2)
C15	0.058 (2)	0.044 (2)	0.0239 (18)	−0.004 (2)	0.0062 (17)	−0.0036 (17)
C16	0.044 (2)	0.048 (2)	0.047 (2)	0.001 (2)	0.0028 (19)	−0.005 (2)

Cl1—C14	1.774 (5)	O5—C6	1.213 (7)
Cl2—C14	1.766 (5)	O6—C12	1.233 (7)
Cl3—C14	1.768 (5)	C1—C2	1.393 (6)
Cl4—C16	1.748 (5)	C1—H1	0.93
Cl5—C16	1.777 (6)	C2—C3	1.380 (7)
Cl6—C16	1.743 (5)	C2—H2	0.93
N1—C5	1.318 (7)	C3—C4	1.375 (6)
N1—C1	1.342 (7)	C3—C6	1.505 (6)
N1—H1A	0.86	C4—C5	1.372 (8)
N2—C6	1.308 (7)	C4—H4	0.93
N2—H2A	0.86	C5—H5	0.93
N2—H2B	0.86	C7—C8	1.377 (7)
N3—C11	1.317 (7)	C7—H7	0.93
N3—C7	1.340 (7)	C8—C9	1.382 (7)
N3—H3A	0.86	C8—H8	0.93
N4—C12	1.314 (7)	C9—C10	1.371 (7)
N4—H4A	0.86	C9—C12	1.499 (6)
N4—H4B	0.86	C10—C11	1.350 (8)
O1—C13	1.213 (6)	C10—H10	0.93
O2—C13	1.233 (6)	C11—H11	0.93
O3—C15	1.242 (6)	C13—C14	1.578 (7)
O4—C15	1.215 (6)	C15—C16	1.566 (7)
C5—N1—C1	121.8 (4)	C7—C8—C9	120.2 (4)
C5—N1—H1A	119.1	C7—C8—H8	119.9
C1—N1—H1A	119.1	C9—C8—H8	119.9
C6—N2—H2A	120	C10—C9—C8	117.8 (4)
C6—N2—H2B	120	C10—C9—C12	118.8 (4)
H2A—N2—H2B	120	C8—C9—C12	123.4 (4)
C11—N3—C7	122.9 (4)	C11—C10—C9	121.1 (5)
C11—N3—H3A	118.6	C11—C10—H10	119.5
C7—N3—H3A	118.6	C9—C10—H10	119.5
C12—N4—H4A	120	N3—C11—C10	119.6 (5)
C12—N4—H4B	120	N3—C11—H11	120.2
H4A—N4—H4B	120	C10—C11—H11	120.2
N1—C1—C2	119.8 (5)	O6—C12—N4	121.5 (5)
N1—C1—H1	120.1	O6—C12—C9	119.7 (5)
C2—C1—H1	120.1	N4—C12—C9	118.8 (4)
C3—C2—C1	118.6 (4)	O1—C13—O2	128.1 (5)
C3—C2—H2	120.7	O1—C13—C14	116.4 (4)
C1—C2—H2	120.7	O2—C13—C14	115.4 (4)
C4—C3—C2	119.6 (4)	C13—C14—Cl2	110.3 (3)
C4—C3—C6	117.6 (4)	C13—C14—Cl3	108.7 (3)
C2—C3—C6	122.8 (4)	Cl2—C14—Cl3	110.3 (3)
C5—C4—C3	119.5 (5)	C13—C14—Cl1	109.5 (3)
C5—C4—H4	120.3	Cl2—C14—Cl1	109.1 (3)
C3—C4—H4	120.3	Cl3—C14—Cl1	108.9 (3)
N1—C5—C4	120.7 (5)	O4—C15—O3	128.1 (5)
N1—C5—H5	119.6	O4—C15—C16	115.3 (4)
C4—C5—H5	119.6	O3—C15—C16	116.2 (4)
O5—C6—N2	122.4 (5)	C15—C16—Cl6	108.4 (3)
O5—C6—C3	119.0 (5)	C15—C16—Cl4	111.6 (4)
N2—C6—C3	118.6 (5)	Cl6—C16—Cl4	110.0 (3)
N3—C7—C8	118.4 (5)	C15—C16—Cl5	112.6 (3)
N3—C7—H7	120.8	Cl6—C16—Cl5	107.4 (3)
C8—C7—H7	120.8	Cl4—C16—Cl5	106.8 (3)
C5—N1—C1—C2	0.5 (8)	C7—N3—C11—C10	1.5 (8)
N1—C1—C2—C3	−0.8 (8)	C9—C10—C11—N3	0.4 (9)
C1—C2—C3—C4	0.7 (8)	C10—C9—C12—O6	0.5 (10)
C1—C2—C3—C6	−179.1 (5)	C8—C9—C12—O6	−177.8 (7)
C2—C3—C4—C5	−0.3 (8)	C10—C9—C12—N4	−177.1 (6)
C6—C3—C4—C5	179.6 (5)	C8—C9—C12—N4	4.6 (8)
C1—N1—C5—C4	0.0 (8)	O1—C13—C14—Cl2	−23.3 (6)
C3—C4—C5—N1	−0.1 (8)	O2—C13—C14—Cl2	159.9 (4)
C4—C3—C6—O5	9.9 (9)	O1—C13—C14—Cl3	97.8 (5)
C2—C3—C6—O5	−170.3 (7)	O2—C13—C14—Cl3	−79.1 (5)
C4—C3—C6—N2	−171.0 (5)	O1—C13—C14—Cl1	−143.3 (5)
C2—C3—C6—N2	8.8 (9)	O2—C13—C14—Cl1	39.8 (6)
C11—N3—C7—C8	−2.1 (8)	O4—C15—C16—Cl6	80.2 (6)
N3—C7—C8—C9	0.8 (8)	O3—C15—C16—Cl6	−93.8 (5)
C7—C8—C9—C10	0.9 (8)	O4—C15—C16—Cl4	−41.1 (6)
C7—C8—C9—C12	179.2 (5)	O3—C15—C16—Cl4	145.0 (5)
C8—C9—C10—C11	−1.6 (9)	O4—C15—C16—Cl5	−161.2 (5)
C12—C9—C10—C11	−180.0 (5)	O3—C15—C16—Cl5	24.9 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	1.78	2.643 (5)	176
N2—H2A···O1ii	0.86	2.03	2.883 (6)	170
N2—H2B···O6iii	0.86	2.06	2.854 (7)	152
N3—H3A···O3iv	0.86	1.8	2.661 (5)	178
N4—H4A···O4v	0.86	2.01	2.858 (6)	169
N4—H4B···O5v	0.86	2.03	2.858 (7)	160
C2—H2···O6iii	0.93	2.34	3.251 (7)	166
C5—H5···O3	0.93	2.6	3.422 (8)	148
C8—H8···O5v	0.93	2.36	3.270 (6)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	1.78	2.643 (5)	176
N2—H2A⋯O1ii	0.86	2.03	2.883 (6)	170
N2—H2B⋯O6iii	0.86	2.06	2.854 (7)	152
N3—H3A⋯O3iv	0.86	1.8	2.661 (5)	178
N4—H4A⋯O4v	0.86	2.01	2.858 (6)	169
N4—H4B⋯O5v	0.86	2.03	2.858 (7)	160
C2—H2⋯O6iii	0.93	2.34	3.251 (7)	166
C5—H5⋯O3	0.93	2.6	3.422 (8)	148
C8—H8⋯O5v	0.93	2.36	3.270 (6)	166

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .