(Di-methyl-phosphor-yl)methanaminium nitrate.

In the crystal of the title salt, C3H11NOP(+)·NO3 (-), dicationic inversion dimers are head-to-tail connected by a pair of strong N-H⋯O hydrogen bonds. The resulting graph-set descriptor of this ring system is R 2 (2)(10). The nitrate counter-anions connect the dicationic dimers via N-H⋯O hydrogen bonds, forming two-dimensional networks in the bc plane.

Related literature

For transition metal complexes of the (dimethylphos­phor­yl)methanamine (dpma) ligand, see: Dodoff et al. (1990 ▶); Borisov et al. (1994 ▶); Trendafilova et al. (1997 ▶); Kochel (2009 ▶). For transition metal complexes of the protonated dpmaH+ ligand, see: Reiss (2013a ▶,b ▶). For simple dpmaH+ salts, see: Reiss & Jörgens (2012 ▶); Lambertz et al. (2013 ▶); Buhl et al. (2013 ▶); Reiss (2013c ▶,d ▶). For a definition of the term tecton, see: Brunet et al. (1997 ▶). For a definition of the term anti­type, see: Lima-de-Faria et al. (1990 ▶). For graph-set theory, see: Etter et al.(1990 ▶); Grell et al. (2002 ▶). For structures showing an analogous topology, see: Holl & Thewalt (1986 ▶); Reiss (2002 ▶); Reiss & Helmbrecht (2012 ▶).

Experimental

Crystal data

C3H11NOP+·NO3 −

M = 170.11

Monoclinic,

a = 8.7718 (3) Å

b = 7.9892 (3) Å

c = 11.2921 (6) Å

β = 96.581 (4)°

V = 786.14 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 290 K

0.63 × 0.38 × 0.19 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.809, T max = 1.000

82785 measured reflections

3770 independent reflections

3313 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.065

S = 1.01

3770 reflections

106 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 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: SHELXL2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013; molecular graphics: DIAMOND (Brandenburg, 2012 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813027694/lh5656sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813027694/lh5656Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813027694/lh5656Isup3.cml

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

C3H11NOP+·NO3−	F(000) = 360
Mr = 170.11	Dx = 1.437 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7718 (3) Å	Cell parameters from 40230 reflections
b = 7.9892 (3) Å	θ = 3.8–36.3°
c = 11.2921 (6) Å	µ = 0.32 mm−1
β = 96.581 (4)°	T = 290 K
V = 786.14 (6) Å3	Block, colourless
Z = 4	0.63 × 0.38 × 0.19 mm

Oxford Diffraction Xcalibur Eos diffractometer	3770 independent reflections
Radiation source: fine-focus sealed tube	3313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 16.2711 pixels mm-1	θmax = 36.4°, θmin = 3.8°
ω scans	h = −14→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.809, Tmax = 1.000	l = −18→18
82785 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.011P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3770 reflections	Δρmax = 0.40 e Å−3
106 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0296 (13)

Experimental. The Raman spectrum was measured using a Bruker MULTIRAM spectrometer (Nd:YAG-Laser at 1064 nm; RT-InGaAs-detector; backscattering geometry); 4000–70 cm-1: 3112 (w), 2994 (s), 2952 (m), 2916 (s), 2854 (w), 2834 (w), 2804 (w), 2654 (w), 2625 (w), 2588 (w), 1645 (w), 1615 (w), 1549 (w), 1430 (w), 1407 (w), 1373 (w), 1309 (w), 1155 (m), 1126 (w), 1092 (w), 1046 (s), 1029 (w), 947 (w), 918 (w), 895 (w), 858 (w), 787 (w), 759 (w), 726 (m), 662 (s), 456 (w), 369 (w), 314 (m), 295 (w), 268 (w), 238 (w), 137 (w), 121 (m), 95 (s), 73 (s). – IR spectroscopic data were recorded on a Digilab FT3400 spectrometer using a MIRacle ATR unit (Pike Technologies); 4000–560 cm-1: 3439 (w), 2993 (s), 2946 (s), 2915 (s), 2885 (s), 2830 (s), 2749 (m), 2722 (m), 2651 (m), 2625 (m), 2403 (w), 2066 (w), 1757 (w), 1638 (m), 1551 (m), 1432 (m), 1420 (m), 1405 (m), 1346 (s), 1330 (s), 1306 (s), 1297 (s), 1157 (s), 1119 (m), 1088 (s), 1045 (w), 1029 (w), 944 (s), 914 (m), 889 (s), 855 (m), 826 (m), 784 (m), 756 (m), 723 (w), 714 (w), 657 (w).

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.

	x	y	z	Uiso*/Ueq
P1	0.16112 (2)	0.75856 (3)	0.06006 (2)	0.02633 (6)
O1	0.04435 (8)	0.70859 (9)	−0.04036 (6)	0.03792 (15)
N1	0.24474 (9)	0.42711 (10)	0.08323 (7)	0.03066 (14)
H11	0.2939 (15)	0.3482 (18)	0.1290 (12)	0.050 (4)*
H12	0.2989 (15)	0.4449 (17)	0.0211 (13)	0.051 (4)*
H13	0.1553 (16)	0.3832 (18)	0.0591 (12)	0.052 (4)*
C1	0.09272 (13)	0.90021 (14)	0.16403 (10)	0.0431 (2)
H1A	0.0774	1.0085	0.1278	0.065*
H1B	0.1667	0.9085	0.2333	0.065*
H1C	−0.0027	0.8598	0.1869	0.065*
C2	0.32841 (11)	0.84891 (13)	0.00985 (10)	0.0400 (2)
H2A	0.3758	0.7689	−0.0377	0.060*
H2B	0.3994	0.8799	0.0774	0.060*
H2C	0.3000	0.9465	−0.0371	0.060*
C3	0.22309 (10)	0.57989 (11)	0.15315 (7)	0.02919 (15)
H3A	0.3190	0.6073	0.2007	0.035*
H3B	0.1473	0.5578	0.2073	0.035*
O2	0.41973 (10)	0.17393 (12)	0.21553 (7)	0.0511 (2)
O3	0.41189 (9)	0.03797 (10)	0.37965 (7)	0.04730 (19)
O4	0.26575 (11)	0.25210 (12)	0.33988 (9)	0.0596 (2)
N2	0.36518 (9)	0.15533 (10)	0.31187 (7)	0.03293 (15)

	U11	U22	U33	U12	U13	U23
P1	0.02420 (9)	0.02590 (9)	0.02829 (10)	−0.00258 (7)	0.00046 (7)	0.00021 (7)
O1	0.0351 (3)	0.0393 (3)	0.0364 (3)	−0.0046 (3)	−0.0083 (3)	−0.0003 (3)
N1	0.0296 (3)	0.0285 (3)	0.0324 (3)	0.0006 (3)	−0.0028 (3)	0.0034 (3)
C1	0.0432 (5)	0.0381 (5)	0.0488 (5)	0.0000 (4)	0.0091 (4)	−0.0112 (4)
C2	0.0363 (4)	0.0384 (5)	0.0463 (5)	−0.0080 (4)	0.0093 (4)	0.0071 (4)
C3	0.0303 (4)	0.0314 (4)	0.0255 (3)	−0.0033 (3)	0.0015 (3)	0.0026 (3)
O2	0.0497 (4)	0.0641 (5)	0.0410 (4)	0.0132 (4)	0.0115 (3)	0.0187 (4)
O3	0.0484 (4)	0.0474 (4)	0.0467 (4)	0.0145 (3)	0.0078 (3)	0.0202 (3)
O4	0.0608 (5)	0.0584 (5)	0.0621 (5)	0.0296 (4)	0.0177 (4)	0.0120 (4)
N2	0.0290 (3)	0.0338 (4)	0.0346 (3)	0.0006 (3)	−0.0021 (3)	0.0046 (3)

P1—O1	1.4927 (7)	C1—H1C	0.9600
P1—C1	1.7834 (10)	C2—H2A	0.9600
P1—C2	1.7851 (9)	C2—H2B	0.9600
P1—C3	1.8186 (9)	C2—H2C	0.9600
N1—C3	1.4777 (12)	C3—H3A	0.9700
N1—H11	0.894 (14)	C3—H3B	0.9700
N1—H12	0.902 (14)	O2—N2	1.2465 (11)
N1—H13	0.874 (14)	O3—N2	1.2494 (10)
C1—H1A	0.9600	O4—N2	1.2336 (11)
C1—H1B	0.9600
O1—P1—C1	114.62 (5)	H1B—C1—H1C	109.5
O1—P1—C2	112.60 (5)	P1—C2—H2A	109.5
C1—P1—C2	107.66 (5)	P1—C2—H2B	109.5
O1—P1—C3	111.27 (4)	H2A—C2—H2B	109.5
C1—P1—C3	102.61 (5)	P1—C2—H2C	109.5
C2—P1—C3	107.38 (5)	H2A—C2—H2C	109.5
C3—N1—H11	110.9 (9)	H2B—C2—H2C	109.5
C3—N1—H12	113.4 (9)	N1—C3—P1	112.81 (6)
H11—N1—H12	107.4 (12)	N1—C3—H3A	109.0
C3—N1—H13	109.4 (9)	P1—C3—H3A	109.0
H11—N1—H13	104.7 (12)	N1—C3—H3B	109.0
H12—N1—H13	110.7 (12)	P1—C3—H3B	109.0
P1—C1—H1A	109.5	H3A—C3—H3B	107.8
P1—C1—H1B	109.5	O4—N2—O2	120.16 (8)
H1A—C1—H1B	109.5	O4—N2—O3	120.34 (9)
P1—C1—H1C	109.5	O2—N2—O3	119.50 (8)
H1A—C1—H1C	109.5
O1—P1—C3—N1	40.98 (7)	C2—P1—C3—N1	−82.67 (7)
C1—P1—C3—N1	164.01 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O2	0.894 (14)	1.966 (15)	2.8555 (11)	173.1 (12)
N1—H12···O3i	0.902 (14)	1.979 (14)	2.8784 (12)	174.5 (13)
N1—H13···O1ii	0.874 (14)	1.888 (14)	2.7493 (10)	168.2 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O2	0.894 (14)	1.966 (15)	2.8555 (11)	173.1 (12)
N1—H12⋯O3i	0.902 (14)	1.979 (14)	2.8784 (12)	174.5 (13)
N1—H13⋯O1ii	0.874 (14)	1.888 (14)	2.7493 (10)	168.2 (13)

Symmetry codes: (i) ; (ii) .