4-[(Adamantan-1-yl)carbamo-yl]pyridinium chloride.

In the title salt, C(16)H(21)N(2)O(+)·Cl(-), the amide group makes a dihedral angle of 24.98 (2)° with respect to the pyridinium ring. In the crystal, both the amide and pyridinium N atoms are involved in N-H⋯Cl hydrogen bonding. Weak inter-molecular C-H⋯Cl and C-H⋯O inter-actions also occur.

Related literature

For the structures and properties of related compounds, see: Fu et al. (2011a ▶,b ▶,c ▶); Dai & Chen (2011 ▶); Xu et al. (2011 ▶); Zheng (2011 ▶).

Experimental

Crystal data

C16H21N2O+·Cl−

M = 292.80

Monoclinic,

a = 7.072 (4) Å

b = 22.691 (13) Å

c = 8.905 (6) Å

β = 91.703 (7)°

V = 1428.3 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 93 K

0.10 × 0.03 × 0.03 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.910, T max = 1.000

13912 measured reflections

3278 independent reflections

2863 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.157

S = 1.19

3278 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022866/xu5543sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022866/xu5543Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022866/xu5543Isup3.cml

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

C16H21N2O+·Cl−	F(000) = 624
Mr = 292.80	Dx = 1.362 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3278 reflections
a = 7.072 (4) Å	θ = 1.8–27.5°
b = 22.691 (13) Å	µ = 0.27 mm−1
c = 8.905 (6) Å	T = 93 K
β = 91.703 (7)°	Block, colourless
V = 1428.3 (15) Å3	0.10 × 0.03 × 0.03 mm
Z = 4

Rigaku Mercury2 diffractometer	3278 independent reflections
Radiation source: fine-focus sealed tube	2863 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 1.8°
CCD profile fitting scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −29→29
Tmin = 0.910, Tmax = 1.000	l = −11→11
13912 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H-atom parameters constrained
S = 1.19	w = 1/[σ2(Fo2) + (0.0868P)2 + 0.3419P] where P = (Fo2 + 2Fc2)/3
3278 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
N2	0.4961 (2)	0.11853 (7)	0.77561 (19)	0.0136 (4)
H2A	0.6014	0.1044	0.7457	0.016*
O1	0.3053 (2)	0.12500 (7)	0.97887 (17)	0.0195 (4)
N1	0.8767 (2)	0.03797 (7)	1.21603 (19)	0.0150 (4)
H1A	0.9604	0.0230	1.2768	0.018*
C4	0.8026 (3)	0.08813 (9)	0.9896 (2)	0.0157 (4)
H4A	0.8425	0.1069	0.9006	0.019*
C8	0.4853 (3)	0.15358 (9)	0.5188 (2)	0.0154 (4)
H8A	0.5154	0.1135	0.4830	0.018*
H8B	0.6058	0.1748	0.5389	0.018*
C12	0.3246 (3)	0.24905 (9)	0.4539 (2)	0.0169 (4)
H12A	0.4446	0.2706	0.4735	0.020*
H12B	0.2500	0.2709	0.3762	0.020*
C6	0.4548 (3)	0.11078 (9)	0.9207 (2)	0.0143 (4)
C7	0.3740 (3)	0.14958 (8)	0.6638 (2)	0.0123 (4)
C3	0.6104 (3)	0.08371 (8)	1.0195 (2)	0.0127 (4)
C2	0.5567 (3)	0.05623 (9)	1.1516 (2)	0.0153 (4)
H2B	0.4267	0.0531	1.1743	0.018*
C9	0.3315 (3)	0.21225 (8)	0.7186 (2)	0.0146 (4)
H9A	0.2611	0.2103	0.8129	0.018*
H9B	0.4515	0.2336	0.7395	0.018*
C13	0.2134 (3)	0.24535 (8)	0.5982 (2)	0.0151 (4)
H13A	0.1859	0.2861	0.6346	0.018*
C5	0.9336 (3)	0.06493 (9)	1.0909 (2)	0.0169 (4)
H5A	1.0648	0.0680	1.0722	0.020*
C10	0.1881 (3)	0.11626 (8)	0.6305 (2)	0.0143 (4)
H10A	0.1160	0.1126	0.7237	0.017*
H10B	0.2160	0.0761	0.5938	0.017*
C16	0.1811 (3)	0.15352 (9)	0.3664 (2)	0.0161 (4)
H16A	0.2081	0.1133	0.3296	0.019*
H16B	0.1052	0.1744	0.2877	0.019*
C15	0.0694 (3)	0.14989 (9)	0.5109 (2)	0.0146 (4)
H15A	−0.0520	0.1284	0.4902	0.017*
C1	0.6932 (3)	0.03367 (9)	1.2493 (2)	0.0165 (4)
H1B	0.6576	0.0151	1.3398	0.020*
C14	0.0263 (3)	0.21217 (9)	0.5695 (2)	0.0157 (4)
H14A	−0.0534	0.2337	0.4946	0.019*
H14B	−0.0438	0.2095	0.6639	0.019*
C11	0.3670 (3)	0.18655 (9)	0.3972 (2)	0.0163 (4)
H11A	0.4396	0.1890	0.3028	0.020*
Cl1	0.77720 (7)	0.01868 (2)	0.63897 (5)	0.01459 (17)

	U11	U22	U33	U12	U13	U23
N2	0.0114 (8)	0.0184 (8)	0.0110 (8)	0.0036 (6)	0.0002 (7)	0.0022 (6)
O1	0.0137 (8)	0.0295 (8)	0.0154 (8)	0.0054 (6)	0.0025 (6)	0.0056 (6)
N1	0.0154 (9)	0.0175 (8)	0.0120 (8)	0.0031 (6)	−0.0045 (7)	0.0002 (6)
C4	0.0164 (11)	0.0172 (10)	0.0135 (10)	−0.0002 (7)	0.0005 (8)	0.0011 (7)
C8	0.0145 (10)	0.0183 (10)	0.0134 (10)	0.0036 (7)	0.0008 (8)	0.0020 (7)
C12	0.0178 (11)	0.0159 (10)	0.0167 (10)	0.0001 (7)	−0.0017 (8)	0.0032 (7)
C6	0.0126 (10)	0.0156 (10)	0.0146 (10)	0.0001 (7)	−0.0017 (8)	0.0015 (7)
C7	0.0109 (9)	0.0141 (9)	0.0117 (9)	0.0010 (7)	−0.0020 (7)	0.0007 (7)
C3	0.0134 (10)	0.0133 (9)	0.0114 (9)	0.0009 (7)	−0.0013 (8)	−0.0009 (7)
C2	0.0137 (10)	0.0173 (9)	0.0149 (10)	0.0018 (7)	0.0004 (8)	0.0019 (8)
C9	0.0161 (10)	0.0145 (10)	0.0130 (10)	0.0011 (7)	−0.0015 (8)	−0.0002 (7)
C13	0.0175 (10)	0.0119 (9)	0.0158 (10)	0.0018 (7)	0.0000 (8)	0.0001 (7)
C5	0.0136 (10)	0.0183 (10)	0.0186 (11)	−0.0007 (7)	−0.0024 (8)	−0.0018 (7)
C10	0.0150 (10)	0.0138 (9)	0.0141 (10)	−0.0011 (7)	−0.0015 (8)	0.0030 (7)
C16	0.0179 (10)	0.0177 (10)	0.0124 (10)	0.0029 (8)	−0.0036 (8)	0.0008 (7)
C15	0.0129 (10)	0.0163 (10)	0.0142 (10)	−0.0014 (7)	−0.0034 (8)	0.0000 (7)
C1	0.0196 (11)	0.0163 (10)	0.0138 (10)	0.0020 (8)	0.0014 (8)	0.0003 (8)
C14	0.0140 (10)	0.0183 (10)	0.0148 (10)	0.0040 (7)	0.0004 (8)	0.0038 (7)
C11	0.0163 (10)	0.0193 (10)	0.0133 (10)	0.0023 (8)	0.0014 (8)	0.0027 (7)
Cl1	0.0136 (3)	0.0161 (3)	0.0139 (3)	0.00244 (16)	−0.00125 (19)	0.00123 (16)

N2—C6	1.345 (3)	C2—C1	1.378 (3)
N2—C7	1.478 (2)	C2—H2B	0.9500
N2—H2A	0.8600	C9—C13	1.536 (3)
O1—C6	1.234 (3)	C9—H9A	0.9900
N1—C1	1.343 (3)	C9—H9B	0.9900
N1—C5	1.343 (3)	C13—C14	1.537 (3)
N1—H1A	0.8600	C13—H13A	1.0000
C4—C5	1.378 (3)	C5—H5A	0.9500
C4—C3	1.396 (3)	C10—C15	1.539 (3)
C4—H4A	0.9500	C10—H10A	0.9900
C8—C7	1.534 (3)	C10—H10B	0.9900
C8—C11	1.542 (3)	C16—C11	1.531 (3)
C8—H8A	0.9900	C16—C15	1.532 (3)
C8—H8B	0.9900	C16—H16A	0.9900
C12—C13	1.529 (3)	C16—H16B	0.9900
C12—C11	1.538 (3)	C15—C14	1.540 (3)
C12—H12A	0.9900	C15—H15A	1.0000
C12—H12B	0.9900	C1—H1B	0.9500
C6—C3	1.518 (3)	C14—H14A	0.9900
C7—C9	1.536 (3)	C14—H14B	0.9900
C7—C10	1.538 (3)	C11—H11A	1.0000
C3—C2	1.394 (3)
C6—N2—C7	124.78 (17)	C12—C13—C9	109.36 (17)
C6—N2—H2A	117.6	C12—C13—C14	110.43 (17)
C7—N2—H2A	117.6	C9—C13—C14	108.90 (16)
C1—N1—C5	122.08 (18)	C12—C13—H13A	109.4
C1—N1—H1A	118.9	C9—C13—H13A	109.4
C5—N1—H1A	119.0	C14—C13—H13A	109.4
C5—C4—C3	119.15 (19)	N1—C5—C4	120.3 (2)
C5—C4—H4A	120.4	N1—C5—H5A	119.8
C3—C4—H4A	120.4	C4—C5—H5A	119.8
C7—C8—C11	109.77 (17)	C7—C10—C15	109.57 (16)
C7—C8—H8A	109.7	C7—C10—H10A	109.8
C11—C8—H8A	109.7	C15—C10—H10A	109.8
C7—C8—H8B	109.7	C7—C10—H10B	109.8
C11—C8—H8B	109.7	C15—C10—H10B	109.8
H8A—C8—H8B	108.2	H10A—C10—H10B	108.2
C13—C12—C11	109.58 (16)	C11—C16—C15	109.68 (16)
C13—C12—H12A	109.8	C11—C16—H16A	109.7
C11—C12—H12A	109.8	C15—C16—H16A	109.7
C13—C12—H12B	109.8	C11—C16—H16B	109.7
C11—C12—H12B	109.8	C15—C16—H16B	109.7
H12A—C12—H12B	108.2	H16A—C16—H16B	108.2
O1—C6—N2	125.65 (19)	C16—C15—C10	108.92 (17)
O1—C6—C3	118.52 (18)	C16—C15—C14	110.33 (16)
N2—C6—C3	115.80 (18)	C10—C15—C14	109.25 (16)
N2—C7—C8	106.92 (16)	C16—C15—H15A	109.4
N2—C7—C9	110.06 (16)	C10—C15—H15A	109.4
C8—C7—C9	108.83 (16)	C14—C15—H15A	109.4
N2—C7—C10	112.01 (16)	N1—C1—C2	119.81 (19)
C8—C7—C10	108.93 (17)	N1—C1—H1B	120.1
C9—C7—C10	110.00 (16)	C2—C1—H1B	120.1
C2—C3—C4	118.94 (18)	C13—C14—C15	109.11 (16)
C2—C3—C6	117.35 (18)	C13—C14—H14A	109.9
C4—C3—C6	123.59 (18)	C15—C14—H14A	109.9
C1—C2—C3	119.7 (2)	C13—C14—H14B	109.9
C1—C2—H2B	120.2	C15—C14—H14B	109.9
C3—C2—H2B	120.2	H14A—C14—H14B	108.3
C13—C9—C7	109.76 (16)	C16—C11—C12	109.60 (17)
C13—C9—H9A	109.7	C16—C11—C8	109.48 (17)
C7—C9—H9A	109.7	C12—C11—C8	108.91 (17)
C13—C9—H9B	109.7	C16—C11—H11A	109.6
C7—C9—H9B	109.7	C12—C11—H11A	109.6
H9A—C9—H9B	108.2	C8—C11—H11A	109.6
C7—N2—C6—O1	4.8 (3)	C7—C9—C13—C14	60.4 (2)
C7—N2—C6—C3	−173.33 (16)	C1—N1—C5—C4	−1.6 (3)
C6—N2—C7—C8	174.15 (18)	C3—C4—C5—N1	0.6 (3)
C6—N2—C7—C9	56.1 (2)	N2—C7—C10—C15	−178.66 (16)
C6—N2—C7—C10	−66.6 (2)	C8—C7—C10—C15	−60.6 (2)
C11—C8—C7—N2	−179.08 (15)	C9—C7—C10—C15	58.6 (2)
C11—C8—C7—C9	−60.2 (2)	C11—C16—C15—C10	−60.5 (2)
C11—C8—C7—C10	59.7 (2)	C11—C16—C15—C14	59.4 (2)
C5—C4—C3—C2	0.4 (3)	C7—C10—C15—C16	61.0 (2)
C5—C4—C3—C6	176.27 (18)	C7—C10—C15—C14	−59.6 (2)
O1—C6—C3—C2	23.6 (3)	C5—N1—C1—C2	1.5 (3)
N2—C6—C3—C2	−158.06 (18)	C3—C2—C1—N1	−0.4 (3)
O1—C6—C3—C4	−152.3 (2)	C12—C13—C14—C15	58.6 (2)
N2—C6—C3—C4	26.0 (3)	C9—C13—C14—C15	−61.5 (2)
C4—C3—C2—C1	−0.5 (3)	C16—C15—C14—C13	−58.5 (2)
C6—C3—C2—C1	−176.61 (18)	C10—C15—C14—C13	61.2 (2)
N2—C7—C9—C13	176.98 (16)	C15—C16—C11—C12	−59.6 (2)
C8—C7—C9—C13	60.1 (2)	C15—C16—C11—C8	59.8 (2)
C10—C7—C9—C13	−59.1 (2)	C13—C12—C11—C16	59.6 (2)
C11—C12—C13—C9	60.3 (2)	C13—C12—C11—C8	−60.1 (2)
C11—C12—C13—C14	−59.5 (2)	C7—C8—C11—C16	−59.5 (2)
C7—C9—C13—C12	−60.4 (2)	C7—C8—C11—C12	60.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.86	2.19	3.020 (2)	161
N2—H2A···Cl1	0.86	2.51	3.272 (2)	148
C1—H1B···Cl1ii	0.95	2.77	3.520 (3)	136
C2—H2B···Cl1iii	0.95	2.76	3.494 (3)	134
C5—H5A···O1iv	0.95	2.31	3.149 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.86	2.19	3.020 (2)	161
N2—H2A⋯Cl1	0.86	2.51	3.272 (2)	148
C1—H1B⋯Cl1ii	0.95	2.77	3.520 (3)	136
C2—H2B⋯Cl1iii	0.95	2.76	3.494 (3)	134
C5—H5A⋯O1iv	0.95	2.31	3.149 (3)	147

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