(Di-methyl-phosphor-yl)methanaminium iodide-(di-methyl-phosphor-yl)methan-amine (1/1).

The asymmetric unit of the title structure, C3H11NOP(+)·I(-)·C3H10NOP, consists of one (di-methyl-phosphor-yl)methanamine (dpma) mol-ecule, one (di-methyl-phosphor-yl)methanaminium (dpmaH) ion and one iodide counter-anion. In the crystal, medium-strong to weak N-H⋯O and N-H⋯N hydrogen bonds connect dpmaH cations and dpma mol-ecules into strands along [001]. The iodide counter-anions form only very weak hydrogen bonds. The crystal used for the diffraction study was found to be an inversion twin with a ratio of 0.83 (2):0.17 (2). The title structure is isotypic to that of dpmaH[ClO4]·dpma [Buhl et al. (2013 ▶). Crystals 3, 350-362].

Related literature

For transition metal complexes of the dpma ligand, see: Dodoff et al. (1990 ▶); Borisov et al. (1994 ▶); Trendafilova et al. (1997 ▶); Kochel (2009 ▶). For transition metal complexes of the cationic dpmaH ligand, see: Reiss (2013a ▶,b ▶). For dpmaH+ salts, see: Reiss & Jörgens (2012 ▶); Buhl et al. (2013 ▶); Lambertz et al. (2013 ▶). For the term tecton, see: Brunet et al. (1997 ▶). For the graph-set analysis method, see: Grell et al. (2002 ▶).

Experimental

Crystal data

C3H11NOP+·I−·C3H10NOP

M = 342.09

Orthorhombic,

a = 17.7791 (3) Å

b = 11.1766 (2) Å

c = 6.91805 (12) Å

V = 1374.69 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.54 mm−1

T = 100 K

0.36 × 0.19 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.538, T max = 0.808

10904 measured reflections

3062 independent reflections

2972 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.016

wR(F 2) = 0.033

S = 1.05

3062 reflections

145 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Refined as an inversion twin.

Flack parameter: 0.173 (17)

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: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011) ▶; software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813019004/zl2559sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019004/zl2559Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019004/zl2559Isup3.cml

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

C3H11NOP+·I−·C3H10NOP	Dx = 1.653 Mg m−3
Mr = 342.09	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 8874 reflections
a = 17.7791 (3) Å	θ = 2.9–29.4°
b = 11.1766 (2) Å	µ = 2.54 mm−1
c = 6.91805 (12) Å	T = 100 K
V = 1374.69 (4) Å3	Block, colorless
Z = 4	0.36 × 0.19 × 0.10 mm
F(000) = 680

Oxford Diffraction Xcalibur Eos diffractometer	3062 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2972 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 16.2711 pixels mm-1	θmax = 27.5°, θmin = 2.9°
ω scans	h = −21→22
Absorption correction: analytical [CrysAlis PRO (Oxford Diffraction, 2009), based on expressions derived by Clark & Reid (1995)]	k = −14→11
Tmin = 0.538, Tmax = 0.808	l = −8→8
10904 measured reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.016	w = 1/[σ2(Fo2) + (0.011P)2 + 0.370P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.033	(Δ/σ)max = 0.003
S = 1.05	Δρmax = 0.32 e Å−3
3062 reflections	Δρmin = −0.28 e Å−3
145 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
6 restraints	Extinction coefficient: 0.00115 (12)
Primary atom site location: structure-invariant direct methods	Absolute structure: Refined as an inversion twin.
Secondary atom site location: difference Fourier map	Flack parameter: 0.173 (17)

Experimental. CrysAlisPro, Version 1.171.34.44, (Oxford Diffraction, 2009). Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by Clark & Reid (1995).

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. Refined as a 2-component inversion twin.

	x	y	z	Uiso*/Ueq
I1	0.57385 (2)	0.73704 (2)	0.75007 (5)	0.01322 (6)
P1	0.34627 (4)	0.54054 (8)	0.66655 (12)	0.00984 (17)
O1	0.31186 (10)	0.62671 (19)	0.8072 (3)	0.0116 (5)
N1	0.33299 (15)	0.7173 (3)	0.3886 (4)	0.0110 (6)
H11	0.3537 (18)	0.748 (3)	0.288 (5)	0.025 (11)*
H12	0.2881 (17)	0.693 (4)	0.364 (5)	0.033 (12)*
H13	0.331 (2)	0.775 (3)	0.481 (6)	0.041 (13)*
C1	0.28010 (15)	0.4322 (3)	0.5842 (4)	0.0125 (7)
H1A	0.2643	0.3833	0.6909	0.019*
H1B	0.3031	0.3827	0.4874	0.019*
H1C	0.2372	0.4721	0.5299	0.019*
C2	0.42584 (14)	0.4612 (2)	0.7564 (8)	0.0164 (6)
H2A	0.4647	0.5170	0.7904	0.025*
H2B	0.4442	0.4077	0.6586	0.025*
H2C	0.4115	0.4161	0.8687	0.025*
C3	0.38262 (16)	0.6192 (3)	0.4555 (5)	0.0124 (7)
H3A	0.4316	0.6521	0.4865	0.015*
H3B	0.3892	0.5624	0.3509	0.015*
P2	0.35541 (4)	0.99276 (7)	0.78259 (13)	0.01040 (17)
O2	0.32571 (12)	0.9051 (2)	0.6371 (3)	0.0154 (5)
N2	0.38890 (15)	0.8119 (3)	1.0417 (4)	0.0120 (6)
H21	0.370 (2)	0.771 (3)	0.957 (5)	0.016 (10)*
H22	0.4349 (17)	0.809 (4)	1.022 (6)	0.033 (12)*
C4	0.44922 (15)	1.0407 (3)	0.7318 (6)	0.0170 (7)
H4A	0.4819	0.9723	0.7271	0.026*
H4B	0.4659	1.0942	0.8315	0.026*
H4C	0.4503	1.0811	0.6094	0.026*
C5	0.30034 (16)	1.1262 (3)	0.7964 (5)	0.0179 (8)
H5A	0.3036	1.1687	0.6761	0.027*
H5B	0.3190	1.1760	0.8989	0.027*
H5C	0.2488	1.1058	0.8217	0.027*
C6	0.35496 (16)	0.9310 (3)	1.0246 (4)	0.0119 (6)
H6A	0.3817	0.9854	1.1095	0.014*
H6B	0.3033	0.9267	1.0695	0.014*

	U11	U22	U33	U12	U13	U23
I1	0.01355 (9)	0.01279 (10)	0.01334 (9)	0.00093 (6)	0.00029 (13)	0.00089 (17)
P1	0.0106 (4)	0.0092 (4)	0.0096 (4)	0.0003 (3)	0.0001 (3)	0.0014 (3)
O1	0.0137 (10)	0.0098 (12)	0.0112 (11)	−0.0002 (8)	0.0022 (8)	−0.0009 (8)
N1	0.0123 (14)	0.0099 (16)	0.0108 (13)	−0.0017 (11)	0.0011 (11)	0.0004 (12)
C1	0.0153 (15)	0.0105 (18)	0.0116 (15)	−0.0020 (12)	−0.0005 (13)	0.0001 (13)
C2	0.0149 (13)	0.0170 (15)	0.0172 (14)	0.0023 (11)	−0.0012 (17)	0.000 (3)
C3	0.0117 (15)	0.0118 (19)	0.0137 (15)	0.0010 (12)	0.0023 (13)	0.0011 (14)
P2	0.0105 (3)	0.0099 (4)	0.0108 (4)	0.0014 (3)	−0.0018 (3)	−0.0004 (3)
O2	0.0182 (11)	0.0133 (13)	0.0146 (12)	0.0035 (9)	−0.0032 (9)	−0.0035 (10)
N2	0.0126 (14)	0.0109 (16)	0.0125 (13)	−0.0015 (11)	−0.0009 (11)	0.0000 (13)
C4	0.0162 (14)	0.0208 (17)	0.0141 (19)	−0.0016 (11)	0.0015 (16)	0.0050 (19)
C5	0.0218 (15)	0.0124 (17)	0.020 (2)	0.0065 (12)	−0.0059 (13)	−0.0033 (13)
C6	0.0113 (15)	0.0113 (18)	0.0130 (15)	−0.0014 (12)	0.0006 (12)	0.0012 (13)

P1—O1	1.500 (2)	P2—O2	1.501 (2)
P1—C2	1.782 (3)	P2—C4	1.787 (3)
P1—C1	1.782 (3)	P2—C5	1.787 (3)
P1—C3	1.823 (3)	P2—C6	1.811 (3)
N1—C3	1.481 (4)	N2—C6	1.467 (4)
N1—H11	0.86 (3)	N2—H21	0.82 (3)
N1—H12	0.86 (3)	N2—H22	0.83 (3)
N1—H13	0.91 (3)	C4—H4A	0.9600
C1—H1A	0.9600	C4—H4B	0.9600
C1—H1B	0.9600	C4—H4C	0.9600
C1—H1C	0.9600	C5—H5A	0.9600
C2—H2A	0.9600	C5—H5B	0.9600
C2—H2B	0.9600	C5—H5C	0.9600
C2—H2C	0.9600	C6—H6A	0.9700
C3—H3A	0.9700	C6—H6B	0.9700
C3—H3B	0.9700
O1—P1—C2	114.65 (19)	H3A—C3—H3B	107.7
O1—P1—C1	112.00 (13)	O2—P2—C4	113.09 (16)
C2—P1—C1	107.30 (15)	O2—P2—C5	112.85 (13)
O1—P1—C3	110.77 (14)	C4—P2—C5	105.77 (15)
C2—P1—C3	103.78 (18)	O2—P2—C6	111.70 (14)
C1—P1—C3	107.81 (15)	C4—P2—C6	107.47 (17)
C3—N1—H11	107 (2)	C5—P2—C6	105.44 (15)
C3—N1—H12	112 (3)	C6—N2—H21	106 (3)
H11—N1—H12	111 (4)	C6—N2—H22	115 (3)
C3—N1—H13	109 (3)	H21—N2—H22	106 (4)
H11—N1—H13	108 (3)	P2—C4—H4A	109.5
H12—N1—H13	109 (4)	P2—C4—H4B	109.5
P1—C1—H1A	109.5	H4A—C4—H4B	109.5
P1—C1—H1B	109.5	P2—C4—H4C	109.5
H1A—C1—H1B	109.5	H4A—C4—H4C	109.5
P1—C1—H1C	109.5	H4B—C4—H4C	109.5
H1A—C1—H1C	109.5	P2—C5—H5A	109.5
H1B—C1—H1C	109.5	P2—C5—H5B	109.5
P1—C2—H2A	109.5	H5A—C5—H5B	109.5
P1—C2—H2B	109.5	P2—C5—H5C	109.5
H2A—C2—H2B	109.5	H5A—C5—H5C	109.5
P1—C2—H2C	109.5	H5B—C5—H5C	109.5
H2A—C2—H2C	109.5	N2—C6—P2	114.7 (2)
H2B—C2—H2C	109.5	N2—C6—H6A	108.6
N1—C3—P1	113.3 (2)	P2—C6—H6A	108.6
N1—C3—H3A	108.9	N2—C6—H6B	108.6
P1—C3—H3A	108.9	P2—C6—H6B	108.6
N1—C3—H3B	108.9	H6A—C6—H6B	107.6
P1—C3—H3B	108.9
O1—P1—C3—N1	−40.2 (3)	O2—P2—C6—N2	49.4 (3)
C2—P1—C3—N1	−163.7 (2)	C4—P2—C6—N2	−75.2 (3)
C1—P1—C3—N1	82.7 (3)	C5—P2—C6—N2	172.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···N2i	0.86 (3)	1.95 (3)	2.805 (4)	173 (3)
N1—H12···O1ii	0.86 (3)	1.96 (3)	2.824 (3)	177 (4)
N1—H13···O2	0.91 (3)	1.81 (3)	2.716 (4)	172 (4)
N2—H21···O1	0.82 (3)	2.17 (3)	2.965 (4)	163 (4)
N2—H22···I1	0.83 (3)	3.21 (3)	3.948 (3)	150 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯N2i	0.86 (3)	1.95 (3)	2.805 (4)	173 (3)
N1—H12⋯O1ii	0.86 (3)	1.96 (3)	2.824 (3)	177 (4)
N1—H13⋯O2	0.91 (3)	1.81 (3)	2.716 (4)	172 (4)
N2—H21⋯O1	0.82 (3)	2.17 (3)	2.965 (4)	163 (4)
N2—H22⋯I1	0.83 (3)	3.21 (3)	3.948 (3)	150 (4)

Symmetry codes: (i) ; (ii) .