(Dimethyl-phosphor-yl)methanaminium chloride.

The crystal structure of the title salt, C(3)H(11)NOP(+)·Cl(-), is primarily built from centrosymmetric dimers of two cations, connected head-to-tail by two charge-supported strong N-H⋯O hydrogen bonds, with a graph-set descriptor R(2) (2)(10). The chloride counter-anions connect these dimeric cationic units into chains along the a-axis direction.

Related literature

For related compounds, see: Varbanov et al. (1987 ▶); Borisov et al. (1994 ▶); Kaukorat et al. (1997 ▶); Zagraniarsky et al. (2008 ▶); Kochel (2009 ▶). For a definition of the term tecton, see: Brunet et al. (1997 ▶); Resnati & Metrangolo (2007 ▶). For the use of anionic phosphinic acid derivatives as supra­molecular tectons, see: Glidewell et al. (2000 ▶); Chen et al. (2010 ▶). For graph-set theory and its applications, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶); Grell et al. (2002 ▶). For hydrogen-bonded phosphinic acid derivatives, see: Reiss & Engel (2008 ▶); Meyer et al. (2010 ▶). For typical NH+⋯Cl− hydrogen-bond parameters, see: Farrugia et al. (2001 ▶); Reiss & Bajorat (2008 ▶); Kovács & Varga (2006 ▶). For the DDM program used to obtain a profile fit of the powder diffraction data of a bulk sample of the title compound, see: Solovyov (2004 ▶).

Experimental

Crystal data

C3H11NOP+·Cl−

M = 143.55

Triclinic,

a = 5.2965 (2) Å

b = 7.7030 (4) Å

c = 8.8035 (3) Å

α = 84.057 (4)°

β = 87.691 (3)°

γ = 89.016 (4)°

V = 356.93 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.66 mm−1

T = 106 K

0.92 × 0.78 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur diffractometer, EOS detector

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.613, T max = 1.000

3785 measured reflections

2076 independent reflections

1968 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.049

S = 1.08

2076 reflections

93 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: DIAMOND (Brandenburg, 2011 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037890/fj2594sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037890/fj2594Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037890/fj2594Isup3.cml

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

C3H11NOP+·Cl−	Z = 2
Mr = 143.55	F(000) = 152
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.2965 (2) Å	Cell parameters from 3569 reflections
b = 7.7030 (4) Å	θ = 3.3–32.6°
c = 8.8035 (3) Å	µ = 0.66 mm−1
α = 84.057 (4)°	T = 106 K
β = 87.691 (3)°	Plate, colourless
γ = 89.016 (4)°	0.92 × 0.78 × 0.05 mm
V = 356.93 (3) Å3

Oxford Diffraction Xcalibur diffractometer, Eos	2076 independent reflections
Radiation source: fine-focus sealed tube	1968 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
Detector resolution: 16.2711 pixels mm-1	θmax = 30.0°, θmin = 3.4°
ω scans	h = −4→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→10
Tmin = 0.613, Tmax = 1.000	l = −12→12
3785 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.049	w = 1/[σ2(Fo2) + (0.012P)2 + 0.2P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2076 reflections	Δρmax = 0.48 e Å−3
93 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.35.21 Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.83052 (4)	−0.22956 (3)	0.16135 (3)	0.01445 (7)
P1	0.48926 (5)	0.25417 (3)	0.28914 (3)	0.00963 (7)
O1	0.65884 (14)	0.18353 (10)	0.41347 (8)	0.01364 (15)
N1	0.31590 (16)	−0.08170 (11)	0.28582 (10)	0.01068 (16)
H1	0.465 (3)	−0.105 (2)	0.2342 (17)	0.024 (4)*
H2	0.192 (3)	−0.142 (2)	0.2566 (18)	0.023 (4)*
H3	0.338 (3)	−0.112 (2)	0.3865 (19)	0.025 (4)*
C1	0.23746 (18)	0.10462 (13)	0.26016 (12)	0.01177 (18)
H1A	0.099 (3)	0.1224 (18)	0.3275 (16)	0.017 (3)*
H1B	0.185 (3)	0.128 (2)	0.1563 (18)	0.022 (4)*
C2	0.3235 (2)	0.45000 (15)	0.32696 (15)	0.0207 (2)
H2A	0.4425	0.5416	0.3322	0.036 (5)*
H2B	0.2293	0.4306	0.4225	0.031 (4)*
H2C	0.2098	0.4830	0.2465	0.029 (4)*
C3	0.6544 (2)	0.29523 (15)	0.10879 (12)	0.0159 (2)
H3A	0.7423	0.1910	0.0845	0.028 (4)*
H3B	0.7737	0.3868	0.1135	0.030 (4)*
H3C	0.5361	0.3300	0.0312	0.020 (4)*

	U11	U22	U33	U12	U13	U23
Cl1	0.00962 (11)	0.01729 (12)	0.01731 (13)	−0.00050 (8)	−0.00147 (8)	−0.00548 (9)
P1	0.00893 (12)	0.00947 (12)	0.01030 (12)	0.00069 (8)	−0.00136 (8)	0.00023 (8)
O1	0.0127 (3)	0.0166 (4)	0.0112 (3)	0.0006 (3)	−0.0029 (3)	0.0011 (3)
N1	0.0099 (4)	0.0110 (4)	0.0113 (4)	−0.0007 (3)	−0.0019 (3)	−0.0013 (3)
C1	0.0085 (4)	0.0118 (4)	0.0146 (5)	0.0006 (3)	−0.0016 (3)	0.0008 (3)
C2	0.0192 (5)	0.0141 (5)	0.0296 (6)	0.0047 (4)	−0.0037 (4)	−0.0056 (4)
C3	0.0131 (5)	0.0222 (5)	0.0117 (5)	−0.0035 (4)	−0.0010 (4)	0.0025 (4)

P1—O1	1.4966 (7)	C1—H1A	0.941 (15)
P1—C3	1.7832 (11)	C1—H1B	0.965 (15)
P1—C2	1.7866 (11)	C2—H2A	0.9600
P1—C1	1.8199 (10)	C2—H2B	0.9600
N1—C1	1.4844 (13)	C2—H2C	0.9600
N1—H1	0.921 (16)	C3—H3A	0.9600
N1—H2	0.872 (16)	C3—H3B	0.9600
N1—H3	0.905 (16)	C3—H3C	0.9600
O1—P1—C3	112.50 (5)	N1—C1—H1B	108.5 (9)
O1—P1—C2	114.00 (5)	P1—C1—H1B	108.3 (9)
C3—P1—C2	107.74 (6)	H1A—C1—H1B	109.1 (13)
O1—P1—C1	112.45 (4)	P1—C2—H2A	109.5
C3—P1—C1	105.97 (5)	P1—C2—H2B	109.5
C2—P1—C1	103.48 (5)	H2A—C2—H2B	109.5
C1—N1—H1	112.4 (9)	P1—C2—H2C	109.5
C1—N1—H2	106.4 (10)	H2A—C2—H2C	109.5
H1—N1—H2	111.5 (14)	H2B—C2—H2C	109.5
C1—N1—H3	109.8 (10)	P1—C3—H3A	109.5
H1—N1—H3	107.6 (13)	P1—C3—H3B	109.5
H2—N1—H3	109.1 (14)	H3A—C3—H3B	109.5
N1—C1—P1	113.12 (7)	P1—C3—H3C	109.5
N1—C1—H1A	107.9 (9)	H3A—C3—H3C	109.5
P1—C1—H1A	109.8 (9)	H3B—C3—H3C	109.5
O1—P1—C1—N1	−34.32 (9)	C2—P1—C1—N1	−157.80 (8)
C3—P1—C1—N1	88.97 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.921 (16)	2.245 (16)	3.1367 (9)	162.8 (13)
N1—H2···Cl1i	0.872 (16)	2.262 (16)	3.1134 (9)	165.3 (14)
N1—H3···O1ii	0.905 (16)	1.791 (16)	2.6900 (12)	172.4 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1	0.921 (16)	2.245 (16)	3.1367 (9)	162.8 (13)
N1—H2⋯Cl1i	0.872 (16)	2.262 (16)	3.1134 (9)	165.3 (14)
N1—H3⋯O1ii	0.905 (16)	1.791 (16)	2.6900 (12)	172.4 (15)

Symmetry codes: (i) ; (ii) .