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

In the title compound, C(16)H(21)N(2)O(+)·Cl(-), the amide group makes a dihedral angle of 25.9 (1)° with respect to the pyridine ring. In the crystal, inter-molecular N-H⋯Cl bonds and weak C-H⋯Cl and C-H⋯O contacts link the cations and the anions into layers parallel to the ac plane. The layers are packed along [010] by hydro-phobic inter-actions between adamantane units.

Related literature

For biomedical properties of adamantane-1-amine derivatives, see: Lees (2005 ▶); Nayyar et al. (2007 ▶). For ferroelectric properties of pyridinium salts, see: Ye et al. (2010 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

C16H21N2O+·Cl−

M = 292.80

Monoclinic,

a = 7.117 (4) Å

b = 23.093 (13) Å

c = 11.241 (5) Å

β = 127.56 (2)°

V = 1464.5 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.950, T max = 0.950

14193 measured reflections

3377 independent reflections

2910 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.139

S = 1.11

3377 reflections

202 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810052499/si2302sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052499/si2302Isup2.hkl

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

C16H21N2O+·Cl−	F(000) = 624
Mr = 292.80	Dx = 1.328 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3642 reflections
a = 7.117 (4) Å	θ = 2.9–27.6°
b = 23.093 (13) Å	µ = 0.26 mm−1
c = 11.241 (5) Å	T = 293 K
β = 127.56 (2)°	Prism, colourless
V = 1464.5 (13) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	3377 independent reflections
Radiation source: fine-focus sealed tube	2910 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 13.6612 pixels mm-1	θmax = 27.6°, θmin = 2.9°
ω scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −30→30
Tmin = 0.950, Tmax = 0.950	l = −14→14
14193 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0598P)2 + 0.5955P] where P = (Fo2 + 2Fc2)/3
3377 reflections	(Δ/σ)max = 0.041
202 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.13642 (10)	−0.01867 (2)	0.85883 (6)	0.03808 (17)
O1	0.3301 (3)	−0.12489 (9)	0.51605 (18)	0.0531 (5)
N1	0.6627 (4)	−0.03832 (8)	0.2831 (2)	0.0406 (5)
H1A	0.6865	−0.0228	0.2198	0.070 (9)*
N2	0.7203 (3)	−0.11813 (8)	0.71977 (19)	0.0345 (4)
H2A	0.8612	−0.1036	0.7512	0.059 (8)*
C1	0.5926 (4)	−0.08374 (9)	0.4772 (2)	0.0307 (4)
C2	0.4096 (4)	−0.05633 (10)	0.3459 (2)	0.0375 (5)
H2B	0.2555	−0.0532	0.3221	0.050 (7)*
C3	0.4491 (4)	−0.03368 (10)	0.2503 (3)	0.0412 (5)
H3A	0.3237	−0.0144	0.1599	0.053 (8)*
C4	0.8423 (4)	−0.06503 (10)	0.4063 (3)	0.0426 (5)
H4A	0.9931	−0.0680	0.4254	0.053 (8)*
C5	0.8118 (4)	−0.08820 (10)	0.5065 (3)	0.0384 (5)
H5A	0.9410	−0.1072	0.5959	0.050 (7)*
C6	0.5359 (4)	−0.11061 (10)	0.5753 (2)	0.0349 (5)
C7	0.7100 (3)	−0.14894 (8)	0.8312 (2)	0.0286 (4)
C8	0.6137 (4)	−0.21041 (9)	0.7764 (2)	0.0381 (5)
H8A	0.4549	−0.2086	0.6847	0.043 (7)*
H8B	0.7099	−0.2307	0.7568	0.059 (8)*
C9	0.9648 (4)	−0.15297 (10)	0.9762 (2)	0.0404 (5)
H9A	1.0617	−0.1731	0.9569	0.057 (8)*
H9B	1.0284	−0.1147	1.0111	0.044 (7)*
C10	0.5588 (4)	−0.11689 (9)	0.8641 (3)	0.0376 (5)
H10A	0.6192	−0.0784	0.8989	0.050 (7)*
H10B	0.3989	−0.1139	0.7738	0.046 (7)*
C11	0.6166 (4)	−0.24278 (9)	0.8968 (3)	0.0415 (5)
H11A	0.5551	−0.2811	0.8615	0.057 (8)*
C12	0.4621 (4)	−0.21057 (10)	0.9256 (3)	0.0427 (5)
H12A	0.3033	−0.2080	0.8341	0.060 (8)*
H12B	0.4575	−0.2313	0.9978	0.060 (8)*
C13	0.5605 (4)	−0.15005 (10)	0.9832 (3)	0.0403 (5)
H13A	0.4650	−0.1300	1.0037	0.064 (8)*
C14	0.8703 (5)	−0.24643 (10)	1.0405 (3)	0.0463 (6)
H14A	0.8734	−0.2675	1.1153	0.056 (8)*
H14B	0.9668	−0.2668	1.0211	0.067 (9)*
C15	0.9674 (4)	−0.18568 (11)	1.0960 (2)	0.0419 (5)
H15A	1.1271	−0.1879	1.1867	0.053 (7)*
C16	0.8150 (5)	−0.15348 (11)	1.1268 (3)	0.0450 (6)
H16A	0.8771	−0.1152	1.1629	0.050 (7)*
H16B	0.8180	−0.1735	1.2028	0.059 (8)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0399 (3)	0.0436 (3)	0.0357 (3)	−0.0034 (2)	0.0256 (3)	0.0040 (2)
O1	0.0297 (9)	0.0891 (13)	0.0340 (9)	−0.0059 (8)	0.0160 (7)	0.0178 (8)
N1	0.0554 (12)	0.0444 (10)	0.0346 (10)	−0.0066 (9)	0.0340 (10)	0.0014 (8)
N2	0.0293 (9)	0.0497 (10)	0.0246 (8)	−0.0055 (7)	0.0166 (8)	0.0054 (7)
C1	0.0320 (10)	0.0365 (10)	0.0262 (10)	−0.0031 (8)	0.0189 (9)	0.0004 (8)
C2	0.0336 (11)	0.0460 (12)	0.0328 (11)	0.0025 (9)	0.0203 (10)	0.0092 (9)
C3	0.0462 (13)	0.0443 (12)	0.0306 (11)	−0.0007 (10)	0.0220 (11)	0.0076 (9)
C4	0.0419 (13)	0.0553 (14)	0.0440 (13)	−0.0019 (10)	0.0331 (12)	−0.0004 (10)
C5	0.0339 (11)	0.0497 (13)	0.0333 (11)	0.0041 (9)	0.0213 (10)	0.0064 (9)
C6	0.0307 (11)	0.0459 (12)	0.0296 (11)	−0.0006 (8)	0.0191 (9)	0.0068 (8)
C7	0.0291 (10)	0.0354 (10)	0.0229 (9)	−0.0015 (8)	0.0166 (8)	0.0036 (7)
C8	0.0458 (13)	0.0383 (12)	0.0332 (11)	−0.0039 (9)	0.0257 (11)	−0.0036 (9)
C9	0.0295 (11)	0.0546 (14)	0.0319 (11)	−0.0049 (9)	0.0160 (10)	0.0079 (10)
C10	0.0453 (13)	0.0372 (11)	0.0369 (12)	0.0088 (9)	0.0286 (11)	0.0078 (9)
C11	0.0527 (14)	0.0303 (11)	0.0400 (12)	−0.0070 (9)	0.0274 (11)	0.0006 (9)
C12	0.0372 (12)	0.0569 (14)	0.0361 (12)	−0.0047 (10)	0.0233 (11)	0.0091 (10)
C13	0.0492 (14)	0.0478 (13)	0.0382 (12)	0.0093 (10)	0.0340 (12)	0.0066 (9)
C14	0.0523 (15)	0.0427 (13)	0.0482 (14)	0.0117 (10)	0.0328 (13)	0.0168 (10)
C15	0.0294 (11)	0.0583 (14)	0.0267 (11)	−0.0015 (9)	0.0112 (9)	0.0122 (9)
C16	0.0571 (15)	0.0491 (14)	0.0297 (12)	−0.0087 (11)	0.0270 (12)	−0.0011 (9)

O1—C6	1.228 (3)	C9—C15	1.535 (3)
N1—C3	1.332 (3)	C9—H9A	0.9600
N1—C4	1.332 (3)	C9—H9B	0.9601
N1—H1A	0.9000	C10—C13	1.536 (3)
N2—C6	1.339 (3)	C10—H10A	0.9602
N2—C7	1.480 (2)	C10—H10B	0.9599
N2—H2A	0.9000	C11—C12	1.517 (3)
C1—C5	1.388 (3)	C11—C14	1.523 (4)
C1—C2	1.390 (3)	C11—H11A	0.9599
C1—C6	1.519 (3)	C12—C13	1.520 (3)
C2—C3	1.369 (3)	C12—H12A	0.9599
C2—H2B	0.9601	C12—H12B	0.9600
C3—H3A	0.9599	C13—C16	1.526 (3)
C4—C5	1.379 (3)	C13—H13A	0.9601
C4—H4A	0.9601	C14—C15	1.520 (4)
C5—H5A	0.9599	C14—H14A	0.9601
C7—C10	1.526 (3)	C14—H14B	0.9600
C7—C8	1.533 (3)	C15—C16	1.518 (3)
C7—C9	1.533 (3)	C15—H15A	0.9600
C8—C11	1.535 (3)	C16—H16A	0.9599
C8—H8A	0.9600	C16—H16B	0.9599
C8—H8B	0.9600
C3—N1—C4	122.33 (19)	C7—C10—C13	109.73 (17)
C3—N1—H1A	118.9	C7—C10—H10A	109.9
C4—N1—H1A	118.8	C13—C10—H10A	110.0
C6—N2—C7	124.82 (18)	C7—C10—H10B	109.6
C6—N2—H2A	117.5	C13—C10—H10B	109.4
C7—N2—H2A	117.7	H10A—C10—H10B	108.2
C5—C1—C2	118.42 (19)	C12—C11—C14	110.2 (2)
C5—C1—C6	123.72 (18)	C12—C11—C8	109.11 (19)
C2—C1—C6	117.73 (19)	C14—C11—C8	109.4 (2)
C3—C2—C1	120.0 (2)	C12—C11—H11A	109.5
C3—C2—H2B	119.9	C14—C11—H11A	109.5
C1—C2—H2B	120.1	C8—C11—H11A	109.1
N1—C3—C2	119.8 (2)	C11—C12—C13	109.63 (18)
N1—C3—H3A	119.8	C11—C12—H12A	109.6
C2—C3—H3A	120.3	C13—C12—H12A	109.5
N1—C4—C5	120.0 (2)	C11—C12—H12B	109.8
N1—C4—H4A	119.9	C13—C12—H12B	110.1
C5—C4—H4A	120.1	H12A—C12—H12B	108.2
C4—C5—C1	119.4 (2)	C12—C13—C16	110.15 (19)
C4—C5—H5A	120.3	C12—C13—C10	109.30 (19)
C1—C5—H5A	120.2	C16—C13—C10	108.74 (19)
O1—C6—N2	125.90 (19)	C12—C13—H13A	109.7
O1—C6—C1	118.23 (19)	C16—C13—H13A	109.2
N2—C6—C1	115.83 (18)	C10—C13—H13A	109.8
N2—C7—C10	112.20 (17)	C15—C14—C11	109.43 (18)
N2—C7—C8	110.26 (16)	C15—C14—H14A	110.2
C10—C7—C8	109.73 (17)	C11—C14—H14A	109.7
N2—C7—C9	107.00 (16)	C15—C14—H14B	109.6
C10—C7—C9	108.87 (18)	C11—C14—H14B	109.7
C8—C7—C9	108.68 (17)	H14A—C14—H14B	108.2
C11—C8—C7	109.54 (17)	C16—C15—C14	109.7 (2)
C11—C8—H8A	110.0	C16—C15—C9	109.31 (19)
C7—C8—H8A	109.7	C14—C15—C9	109.5 (2)
C11—C8—H8B	109.7	C16—C15—H15A	109.4
C7—C8—H8B	109.7	C14—C15—H15A	109.5
H8A—C8—H8B	108.2	C9—C15—H15A	109.4
C15—C9—C7	109.69 (17)	C15—C16—C13	109.68 (19)
C15—C9—H9A	109.6	C15—C16—H16A	109.8
C7—C9—H9A	109.6	C13—C16—H16A	110.1
C15—C9—H9B	110.1	C15—C16—H16B	109.6
C7—C9—H9B	109.6	C13—C16—H16B	109.5
H9A—C9—H9B	108.2	H16A—C16—H16B	108.1
C5—C1—C2—C3	−1.1 (3)	C8—C7—C9—C15	−59.8 (2)
C6—C1—C2—C3	−177.1 (2)	N2—C7—C10—C13	−178.48 (17)
C4—N1—C3—C2	0.7 (3)	C8—C7—C10—C13	58.6 (2)
C1—C2—C3—N1	0.4 (3)	C9—C7—C10—C13	−60.2 (2)
C3—N1—C4—C5	−1.1 (4)	C7—C8—C11—C12	60.1 (2)
N1—C4—C5—C1	0.4 (4)	C7—C8—C11—C14	−60.6 (2)
C2—C1—C5—C4	0.6 (3)	C14—C11—C12—C13	58.8 (2)
C6—C1—C5—C4	176.4 (2)	C8—C11—C12—C13	−61.3 (2)
C7—N2—C6—O1	4.6 (4)	C11—C12—C13—C16	−58.4 (2)
C7—N2—C6—C1	−173.26 (18)	C11—C12—C13—C10	61.0 (2)
C5—C1—C6—O1	−151.3 (2)	C7—C10—C13—C12	−59.5 (2)
C2—C1—C6—O1	24.5 (3)	C7—C10—C13—C16	60.8 (2)
C5—C1—C6—N2	26.7 (3)	C12—C11—C14—C15	−59.6 (2)
C2—C1—C6—N2	−157.5 (2)	C8—C11—C14—C15	60.4 (3)
C6—N2—C7—C10	−66.8 (3)	C11—C14—C15—C16	59.8 (2)
C6—N2—C7—C8	55.8 (3)	C11—C14—C15—C9	−60.2 (3)
C6—N2—C7—C9	173.9 (2)	C7—C9—C15—C16	−59.9 (2)
N2—C7—C8—C11	177.02 (18)	C7—C9—C15—C14	60.2 (3)
C10—C7—C8—C11	−58.9 (2)	C14—C15—C16—C13	−59.6 (2)
C9—C7—C8—C11	60.0 (2)	C9—C15—C16—C13	60.6 (2)
N2—C7—C9—C15	−178.89 (18)	C12—C13—C16—C15	59.0 (2)
C10—C7—C9—C15	59.6 (2)	C10—C13—C16—C15	−60.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.90	2.16	3.017 (2)	160.
N2—H2A···Cl1ii	0.90	2.50	3.293 (2)	147.
C2—H2B···Cl1iii	0.96	2.79	3.535 (3)	136.
C3—H3A···Cl1iv	0.96	2.78	3.536 (3)	136.
C4—H4A···O1ii	0.96	2.35	3.203 (3)	147.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.90	2.16	3.017 (2)	160
N2—H2A⋯Cl1ii	0.90	2.50	3.293 (2)	147
C2—H2B⋯Cl1iii	0.96	2.79	3.535 (3)	136
C3—H3A⋯Cl1iv	0.96	2.78	3.536 (3)	136
C4—H4A⋯O1ii	0.96	2.35	3.203 (3)	147

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