1,1,4,7,7-Penta-methyl-diethylenetri-ammonium trinitrate.

In the title compound, C9H26N3 (3+)·3NO3 (-), the triprotonated 1,1,4,7,7-penta-methyl-diethylenetri-amine mol-ecules are linked to the nitrate anions by multiple bifurcated N-H⋯(O,O) and weak C-H⋯O hydrogen bonds. The organic cation is characterized by N-C-C-N torsion angles of -176.2 (2) and 176.6 (2)°.

Related literature

For related structures, see: Marouani et al. (2012 ▶); Gatfaoui et al. (2013 ▶); Kefi et al. (2013 ▶); Ben Slimane & Smirani (2008 ▶); Morawitz et al. (2005 ▶). For a discussion on hydrogen bonding, see: Brown (1976 ▶); Blessing (1986 ▶).

Experimental

Crystal data

C9H26N3 3+·3NO3 −

M = 362.36

Triclinic,

a = 5.964 (2) Å

b = 7.018 (1) Å

c = 21.688 (2) Å

α = 91.90 (2)°

β = 90.60 (2)°

γ = 102.45 (3)°

V = 885.8 (3) Å3

Z = 2

Ag Kα radiation

λ = 0.56083 Å

μ = 0.07 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Enraf–Nonius CAD4 diffractometer

3582 measured reflections

3128 independent reflections

2125 reflections with I > 2σ(I)

R int = 0.030

2 standard reflections every 120 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.184

S = 1.05

3128 reflections

234 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814001469/bh2492sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001469/bh2492Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001469/bh2492Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C9H26N6O9	Z = 2
Mr = 362.36	F(000) = 388
Triclinic, P1	Dx = 1.359 Mg m−3
Hall symbol: -P 1	Ag Kα radiation, λ = 0.56083 Å
a = 5.964 (2) Å	Cell parameters from 25 reflections
b = 7.018 (1) Å	θ = 9–11°
c = 21.688 (2) Å	µ = 0.07 mm−1
α = 91.90 (2)°	T = 293 K
β = 90.60 (2)°	Prism, colourless
γ = 102.45 (3)°	0.40 × 0.35 × 0.30 mm
V = 885.8 (3) Å3

Enraf–Nonius CAD4 diffractometer	Rint = 0.030
Radiation source: fine-focus sealed tube	θmax = 19.5°, θmin = 2.2°
Graphite monochromator	h = −7→7
non–profiled ω scans	k = −8→8
3582 measured reflections	l = −2→25
3128 independent reflections	2 standard reflections every 120 min
2125 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0789P)2 + 0.6513P] where P = (Fo2 + 2Fc2)/3
3128 reflections	(Δ/σ)max < 0.001
234 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.24 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
N1	0.4083 (4)	0.2269 (4)	0.40433 (11)	0.0411 (6)
N2	0.5838 (4)	0.0897 (3)	0.24407 (10)	0.0344 (5)
N3	0.3516 (4)	0.2565 (4)	0.09611 (11)	0.0388 (6)
N4	−0.0530 (5)	0.8384 (4)	0.08493 (13)	0.0548 (7)
N5	0.9855 (5)	0.5138 (4)	0.24709 (13)	0.0519 (7)
N6	0.0036 (5)	0.8141 (4)	0.41497 (14)	0.0601 (7)
O1	−0.0634 (4)	0.9934 (4)	0.11371 (13)	0.0711 (7)
O2	−0.2111 (5)	0.6968 (5)	0.08600 (17)	0.1129 (12)
O3	0.1225 (5)	0.8341 (4)	0.05677 (15)	0.0926 (10)
O4	0.7958 (5)	0.5372 (4)	0.26319 (15)	0.0839 (9)
O5	1.0059 (4)	0.3412 (3)	0.23999 (13)	0.0675 (7)
O6	1.1418 (5)	0.6488 (5)	0.23730 (18)	0.1128 (12)
O7	−0.0504 (5)	0.9697 (5)	0.40675 (18)	0.1064 (11)
O8	−0.1275 (6)	0.6643 (5)	0.4269 (2)	0.1306 (15)
O9	0.2109 (4)	0.8175 (4)	0.41010 (15)	0.0816 (8)
C1	0.5618 (5)	0.1954 (4)	0.35333 (13)	0.0433 (7)
H1A	0.6433	0.0955	0.3644	0.052*
H1B	0.6746	0.3152	0.3474	0.052*
C2	0.4284 (4)	0.1337 (4)	0.29386 (13)	0.0411 (7)
H2A	0.3090	0.0186	0.3003	0.049*
H2B	0.3553	0.2373	0.2812	0.049*
C3	0.4709 (5)	0.0753 (4)	0.18173 (13)	0.0395 (7)
H3A	0.3187	−0.0081	0.1834	0.047*
H3B	0.5593	0.0157	0.1524	0.047*
C4	0.4516 (5)	0.2739 (4)	0.15978 (13)	0.0424 (7)
H4A	0.3550	0.3304	0.1875	0.051*
H4B	0.6026	0.3600	0.1603	0.051*
C5	0.5362 (6)	0.2467 (5)	0.46408 (14)	0.0561 (8)
H5A	0.6040	0.1357	0.4688	0.084*
H5B	0.4326	0.2537	0.4972	0.084*
H5C	0.6548	0.3636	0.4649	0.084*
C6	0.3009 (7)	0.3951 (6)	0.39551 (19)	0.0763 (12)
H6A	0.4184	0.5104	0.3903	0.114*
H6B	0.2120	0.4134	0.4310	0.114*
H6C	0.2027	0.3708	0.3595	0.114*
C7	0.6704 (5)	−0.0917 (4)	0.25532 (15)	0.0485 (8)
H7A	0.5432	−0.2019	0.2553	0.073*
H7B	0.7494	−0.0783	0.2945	0.073*
H7C	0.7740	−0.1109	0.2233	0.073*
C8	0.2505 (6)	0.4277 (5)	0.08285 (16)	0.0559 (8)
H8A	0.3696	0.5443	0.0843	0.084*
H8B	0.1376	0.4393	0.1131	0.084*
H8C	0.1794	0.4099	0.0426	0.084*
C9	0.5213 (6)	0.2317 (5)	0.04887 (15)	0.0597 (9)
H9A	0.6439	0.3457	0.0496	0.090*
H9B	0.4479	0.2142	0.0089	0.090*
H9C	0.5821	0.1193	0.0575	0.090*
H1	0.304 (6)	0.114 (5)	0.4038 (14)	0.051 (9)*
H2	0.701 (5)	0.188 (4)	0.2414 (12)	0.036 (8)*
H3	0.247 (6)	0.148 (5)	0.0925 (14)	0.051 (9)*

	U11	U22	U33	U12	U13	U23
N1	0.0408 (13)	0.0376 (13)	0.0435 (14)	0.0050 (11)	0.0083 (11)	−0.0007 (10)
N2	0.0270 (11)	0.0358 (13)	0.0420 (13)	0.0093 (10)	0.0055 (10)	0.0069 (10)
N3	0.0332 (12)	0.0402 (14)	0.0420 (14)	0.0044 (10)	0.0009 (10)	0.0080 (10)
N4	0.0470 (16)	0.0527 (17)	0.0597 (17)	−0.0003 (13)	−0.0091 (14)	0.0049 (13)
N5	0.0464 (16)	0.0452 (16)	0.0606 (17)	0.0017 (13)	−0.0009 (13)	0.0042 (12)
N6	0.0506 (17)	0.0542 (18)	0.073 (2)	0.0052 (14)	0.0031 (14)	0.0033 (14)
O1	0.0511 (14)	0.0646 (16)	0.097 (2)	0.0111 (12)	0.0169 (13)	−0.0059 (14)
O2	0.088 (2)	0.092 (2)	0.129 (3)	−0.0453 (18)	−0.0175 (19)	0.0045 (19)
O3	0.083 (2)	0.087 (2)	0.110 (2)	0.0251 (16)	0.0385 (18)	−0.0092 (17)
O4	0.0724 (18)	0.0576 (16)	0.131 (2)	0.0310 (13)	0.0247 (17)	0.0134 (15)
O5	0.0396 (12)	0.0509 (14)	0.114 (2)	0.0139 (10)	0.0117 (12)	0.0000 (13)
O6	0.084 (2)	0.074 (2)	0.158 (3)	−0.0324 (17)	0.019 (2)	0.003 (2)
O7	0.083 (2)	0.082 (2)	0.166 (3)	0.0474 (17)	−0.029 (2)	−0.004 (2)
O8	0.099 (2)	0.079 (2)	0.192 (4)	−0.0311 (19)	0.061 (3)	0.003 (2)
O9	0.0541 (16)	0.0658 (17)	0.127 (2)	0.0163 (12)	0.0059 (15)	0.0145 (16)
C1	0.0335 (14)	0.0544 (18)	0.0443 (17)	0.0141 (13)	0.0033 (12)	0.0036 (13)
C2	0.0303 (14)	0.0530 (17)	0.0434 (16)	0.0157 (12)	0.0070 (12)	0.0056 (13)
C3	0.0363 (14)	0.0413 (16)	0.0421 (16)	0.0109 (12)	0.0004 (12)	0.0031 (12)
C4	0.0443 (16)	0.0460 (16)	0.0398 (16)	0.0161 (13)	0.0021 (13)	0.0025 (12)
C5	0.072 (2)	0.0535 (19)	0.0418 (18)	0.0111 (16)	0.0008 (16)	0.0014 (14)
C6	0.078 (3)	0.086 (3)	0.078 (3)	0.052 (2)	−0.011 (2)	−0.019 (2)
C7	0.0501 (17)	0.0454 (17)	0.0566 (19)	0.0240 (14)	0.0011 (14)	0.0076 (14)
C8	0.0538 (19)	0.062 (2)	0.059 (2)	0.0257 (16)	0.0027 (16)	0.0186 (16)
C9	0.067 (2)	0.070 (2)	0.0472 (19)	0.0258 (18)	0.0158 (16)	0.0065 (16)

N1—C6	1.475 (4)	C1—H1B	0.9700
N1—C5	1.484 (4)	C2—H2A	0.9700
N1—C1	1.484 (3)	C2—H2B	0.9700
N1—H1	0.90 (3)	C3—C4	1.515 (4)
N2—C3	1.495 (3)	C3—H3A	0.9700
N2—C2	1.498 (3)	C3—H3B	0.9700
N2—C7	1.499 (3)	C4—H4A	0.9700
N2—H2	0.87 (3)	C4—H4B	0.9700
N3—C9	1.479 (4)	C5—H5A	0.9600
N3—C4	1.489 (4)	C5—H5B	0.9600
N3—C8	1.491 (4)	C5—H5C	0.9600
N3—H3	0.87 (3)	C6—H6A	0.9600
N4—O2	1.214 (4)	C6—H6B	0.9600
N4—O3	1.223 (4)	C6—H6C	0.9600
N4—O1	1.249 (4)	C7—H7A	0.9600
N5—O6	1.204 (3)	C7—H7B	0.9600
N5—O4	1.230 (3)	C7—H7C	0.9600
N5—O5	1.248 (3)	C8—H8A	0.9600
N6—O8	1.205 (4)	C8—H8B	0.9600
N6—O7	1.221 (4)	C8—H8C	0.9600
N6—O9	1.237 (4)	C9—H9A	0.9600
C1—C2	1.509 (4)	C9—H9B	0.9600
C1—H1A	0.9700	C9—H9C	0.9600
C6—N1—C5	111.1 (3)	C4—C3—H3A	109.3
C6—N1—C1	113.2 (3)	N2—C3—H3B	109.3
C5—N1—C1	109.8 (2)	C4—C3—H3B	109.3
C6—N1—H1	112 (2)	H3A—C3—H3B	107.9
C5—N1—H1	108 (2)	N3—C4—C3	110.5 (2)
C1—N1—H1	102 (2)	N3—C4—H4A	109.6
C3—N2—C2	111.8 (2)	C3—C4—H4A	109.6
C3—N2—C7	110.1 (2)	N3—C4—H4B	109.6
C2—N2—C7	112.4 (2)	C3—C4—H4B	109.6
C3—N2—H2	103.5 (18)	H4A—C4—H4B	108.1
C2—N2—H2	109.4 (18)	N1—C5—H5A	109.5
C7—N2—H2	109.2 (18)	N1—C5—H5B	109.5
C9—N3—C4	112.2 (2)	H5A—C5—H5B	109.5
C9—N3—C8	110.5 (2)	N1—C5—H5C	109.5
C4—N3—C8	110.9 (2)	H5A—C5—H5C	109.5
C9—N3—H3	104 (2)	H5B—C5—H5C	109.5
C4—N3—H3	109 (2)	N1—C6—H6A	109.5
C8—N3—H3	111 (2)	N1—C6—H6B	109.5
O2—N4—O3	121.6 (3)	H6A—C6—H6B	109.5
O2—N4—O1	120.7 (3)	N1—C6—H6C	109.5
O3—N4—O1	117.7 (3)	H6A—C6—H6C	109.5
O6—N5—O4	122.3 (3)	H6B—C6—H6C	109.5
O6—N5—O5	121.5 (3)	N2—C7—H7A	109.5
O4—N5—O5	116.2 (3)	N2—C7—H7B	109.5
O8—N6—O7	125.1 (4)	H7A—C7—H7B	109.5
O8—N6—O9	119.9 (3)	N2—C7—H7C	109.5
O7—N6—O9	114.9 (3)	H7A—C7—H7C	109.5
N1—C1—C2	111.4 (2)	H7B—C7—H7C	109.5
N1—C1—H1A	109.3	N3—C8—H8A	109.5
C2—C1—H1A	109.3	N3—C8—H8B	109.5
N1—C1—H1B	109.3	H8A—C8—H8B	109.5
C2—C1—H1B	109.3	N3—C8—H8C	109.5
H1A—C1—H1B	108.0	H8A—C8—H8C	109.5
N2—C2—C1	110.6 (2)	H8B—C8—H8C	109.5
N2—C2—H2A	109.5	N3—C9—H9A	109.5
C1—C2—H2A	109.5	N3—C9—H9B	109.5
N2—C2—H2B	109.5	H9A—C9—H9B	109.5
C1—C2—H2B	109.5	N3—C9—H9C	109.5
H2A—C2—H2B	108.1	H9A—C9—H9C	109.5
N2—C3—C4	111.7 (2)	H9B—C9—H9C	109.5
N2—C3—H3A	109.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O9i	0.90 (3)	2.04 (3)	2.868 (4)	153 (3)
N1—H1···O7i	0.90 (3)	2.14 (3)	2.937 (4)	147 (3)
N2—H2···O5	0.87 (3)	1.90 (3)	2.749 (3)	162 (3)
N2—H2···O4	0.87 (3)	2.42 (3)	3.134 (4)	139 (2)
N3—H3···O1i	0.87 (3)	2.00 (3)	2.789 (4)	149 (3)
N3—H3···O3i	0.87 (3)	2.28 (3)	3.073 (4)	152 (3)
C1—H1A···O7ii	0.97	2.38	3.293 (4)	156
C1—H1B···O4	0.97	2.45	3.232 (4)	137
C2—H2B···O5iii	0.97	2.52	3.386 (4)	149
C3—H3B···O1ii	0.97	2.44	3.308 (4)	148
C4—H4A···O5iii	0.97	2.40	3.301 (4)	155
C5—H5C···O8iv	0.96	2.40	3.305 (5)	156
C7—H7A···O6v	0.96	2.42	3.295 (4)	152
C8—H8A···O2iv	0.96	2.50	3.355 (5)	149
C9—H9A···O2iv	0.96	2.53	3.377 (5)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O9i	0.90 (3)	2.04 (3)	2.868 (4)	153 (3)
N1—H1⋯O7i	0.90 (3)	2.14 (3)	2.937 (4)	147 (3)
N2—H2⋯O5	0.87 (3)	1.90 (3)	2.749 (3)	162 (3)
N2—H2⋯O4	0.87 (3)	2.42 (3)	3.134 (4)	139 (2)
N3—H3⋯O1i	0.87 (3)	2.00 (3)	2.789 (4)	149 (3)
N3—H3⋯O3i	0.87 (3)	2.28 (3)	3.073 (4)	152 (3)
C1—H1A⋯O7ii	0.97	2.38	3.293 (4)	156
C1—H1B⋯O4	0.97	2.45	3.232 (4)	137
C2—H2B⋯O5iii	0.97	2.52	3.386 (4)	149
C3—H3B⋯O1ii	0.97	2.44	3.308 (4)	148
C4—H4A⋯O5iii	0.97	2.40	3.301 (4)	155
C5—H5C⋯O8iv	0.96	2.40	3.305 (5)	156
C7—H7A⋯O6v	0.96	2.42	3.295 (4)	152
C8—H8A⋯O2iv	0.96	2.50	3.355 (5)	149
C9—H9A⋯O2iv	0.96	2.53	3.377 (5)	148

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