1,1,4,7,7-Penta­methyl­diethylenetriammonium bis­(hexa­fluoro­phosphate)

The title compound, C₉H₂₅N₃²⁺·2PF₆^-, consists of discrete hexa­fluoro­phosphate anions and 1,1,4,7,7-penta­methyl­diethylenetriamine cations. The geometric parameters are in the usual ranges. Only one PF₆^- cation forms hydrogen bonds with both NH donors of the cation.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.105
• Data-to-parameter ratio = 17.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.29 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         P2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

1,1,4,7,7-Pentamethyldiethylenetriammonium bis(hexafluorophosphate)

Crystal data

C9H25N3^2+·2PF6^−	F(000) = 952
Mr = 465.26	Dx = 1.635 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 26656 reflections
a = 8.7310 (5) Å	θ = 2.0–27.5°
b = 12.7348 (5) Å	µ = 0.34 mm^−1
c = 17.2366 (10) Å	T = 173 K
β = 99.440 (5)°	Block, light brown
V = 1890.54 (17) Å^3	0.49 × 0.48 × 0.38 mm
Z = 4

Data collection

Stoe IPDS-II two-circle diffractometer	4201 independent reflections
Radiation source: fine-focus sealed tube	4042 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
ω scans	θmax = 27.2°, θmin = 2.0°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −11→11
Tmin = 0.850, Tmax = 0.881	k = −15→16
26656 measured reflections	l = −22→22

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.048P)^2 + 0.8541P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
4201 reflections	Δρmax = 0.46 e Å^−3
244 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.55713 (15)	0.73597 (11)	0.67615 (8)	0.0285 (3)
H1	0.521 (2)	0.7403 (16)	0.6253 (13)	0.030 (5)*
C2	0.50032 (18)	0.63398 (13)	0.70568 (9)	0.0309 (3)
H2A	0.5244	0.6325	0.7638	0.037*
H2B	0.5556	0.5747	0.6854	0.037*
C3	0.32702 (18)	0.62042 (13)	0.67993 (9)	0.0294 (3)
H3A	0.2960	0.5496	0.6952	0.035*
H3B	0.2712	0.6727	0.7074	0.035*
N4	0.28146 (14)	0.63364 (10)	0.59412 (7)	0.0234 (3)
C5	0.11197 (17)	0.64782 (13)	0.57488 (9)	0.0273 (3)
H5A	0.0773	0.6951	0.6142	0.033*
H5B	0.0603	0.5791	0.5780	0.033*
C6	0.06277 (17)	0.69373 (12)	0.49304 (9)	0.0279 (3)
H6A	0.0805	0.6410	0.4533	0.033*
H6B	−0.0497	0.7095	0.4851	0.033*
N7	0.15044 (14)	0.79213 (10)	0.48086 (7)	0.0228 (3)
H7	0.247 (2)	0.7775 (15)	0.4880 (10)	0.021 (4)*
C11	0.7303 (2)	0.73427 (18)	0.68602 (12)	0.0437 (4)
H11A	0.7640	0.6708	0.6614	0.065*
H11B	0.7737	0.7344	0.7422	0.065*
H11C	0.7666	0.7965	0.6609	0.065*
C12	0.5012 (3)	0.83085 (16)	0.71284 (12)	0.0459 (5)
H12A	0.3875	0.8300	0.7056	0.069*
H12B	0.5360	0.8938	0.6880	0.069*
H12C	0.5432	0.8315	0.7692	0.069*
C41	0.3309 (2)	0.54379 (15)	0.55116 (11)	0.0414 (4)
H41A	0.2996	0.5549	0.4945	0.062*
H41B	0.2820	0.4797	0.5669	0.062*
H41C	0.4440	0.5367	0.5634	0.062*
C71	0.1069 (2)	0.83109 (16)	0.39826 (10)	0.0385 (4)
H71A	0.1199	0.7744	0.3615	0.058*
H71B	0.1740	0.8902	0.3897	0.058*
H71C	−0.0016	0.8542	0.3895	0.058*
C72	0.1312 (2)	0.87689 (13)	0.53826 (10)	0.0353 (4)
H72A	0.1908	0.9388	0.5273	0.053*
H72B	0.1690	0.8520	0.5918	0.053*
H72C	0.0211	0.8955	0.5334	0.053*
P1	0.58939 (4)	0.80775 (4)	0.45549 (2)	0.02862 (14)
F11	0.52843 (17)	0.90773 (12)	0.40500 (7)	0.0583 (4)
F12	0.64812 (15)	0.70699 (10)	0.50812 (7)	0.0491 (3)
F13	0.44607 (13)	0.74096 (12)	0.41134 (8)	0.0574 (4)
F14	0.73031 (13)	0.87317 (11)	0.50165 (7)	0.0510 (3)
F15	0.69177 (13)	0.77218 (13)	0.39144 (7)	0.0543 (3)
F16	0.48438 (11)	0.84077 (9)	0.52127 (6)	0.0365 (2)
P2	0.93727 (5)	0.45187 (3)	0.74275 (2)	0.02530 (13)
F21	0.88244 (15)	0.33355 (9)	0.75601 (7)	0.0496 (3)
F22	0.81244 (14)	0.46116 (11)	0.66377 (7)	0.0502 (3)
F23	1.06169 (14)	0.44217 (9)	0.82187 (6)	0.0441 (3)
F24	0.99459 (13)	0.56928 (8)	0.73140 (6)	0.0391 (3)
F25	1.06211 (13)	0.40750 (9)	0.69222 (6)	0.0397 (3)
F26	0.81112 (13)	0.49548 (9)	0.79276 (6)	0.0406 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0285 (6)	0.0342 (7)	0.0206 (6)	−0.0053 (5)	−0.0024 (5)	0.0024 (5)
C2	0.0316 (8)	0.0315 (8)	0.0283 (7)	0.0008 (6)	0.0009 (6)	0.0063 (6)
C3	0.0312 (7)	0.0328 (8)	0.0237 (7)	−0.0031 (6)	0.0033 (6)	0.0064 (6)
N4	0.0247 (6)	0.0242 (6)	0.0212 (6)	−0.0003 (5)	0.0032 (4)	0.0003 (4)
C5	0.0254 (7)	0.0308 (8)	0.0257 (7)	−0.0034 (6)	0.0046 (5)	0.0049 (6)
C6	0.0259 (7)	0.0299 (7)	0.0262 (7)	−0.0036 (6)	−0.0003 (5)	0.0023 (6)
N7	0.0221 (6)	0.0254 (6)	0.0208 (6)	0.0029 (5)	0.0027 (4)	0.0025 (5)
C11	0.0289 (8)	0.0574 (12)	0.0417 (10)	−0.0044 (8)	−0.0031 (7)	0.0051 (8)
C12	0.0600 (12)	0.0365 (10)	0.0394 (10)	0.0061 (8)	0.0027 (9)	−0.0051 (8)
C41	0.0466 (10)	0.0362 (9)	0.0404 (9)	0.0108 (7)	0.0040 (8)	−0.0095 (7)
C71	0.0443 (9)	0.0457 (10)	0.0242 (7)	0.0029 (8)	0.0018 (6)	0.0119 (7)
C72	0.0414 (9)	0.0277 (8)	0.0368 (9)	0.0052 (6)	0.0069 (7)	−0.0062 (6)
P1	0.0231 (2)	0.0415 (3)	0.0217 (2)	−0.00106 (15)	0.00503 (14)	0.00106 (15)
F11	0.0692 (8)	0.0677 (9)	0.0398 (6)	0.0208 (7)	0.0139 (6)	0.0228 (6)
F12	0.0660 (8)	0.0411 (6)	0.0408 (6)	0.0127 (5)	0.0104 (5)	0.0055 (5)
F13	0.0360 (6)	0.0812 (10)	0.0531 (7)	−0.0120 (6)	0.0020 (5)	−0.0306 (7)
F14	0.0352 (6)	0.0633 (8)	0.0537 (7)	−0.0183 (5)	0.0049 (5)	−0.0055 (6)
F15	0.0396 (6)	0.0934 (10)	0.0332 (6)	0.0126 (6)	0.0155 (4)	−0.0033 (6)
F16	0.0351 (5)	0.0468 (6)	0.0303 (5)	−0.0002 (4)	0.0133 (4)	−0.0030 (4)
P2	0.0310 (2)	0.0249 (2)	0.0212 (2)	−0.00290 (14)	0.00796 (15)	0.00019 (13)
F21	0.0690 (8)	0.0276 (5)	0.0590 (7)	−0.0132 (5)	0.0306 (6)	−0.0033 (5)
F22	0.0469 (6)	0.0659 (8)	0.0329 (6)	0.0038 (5)	−0.0074 (5)	−0.0082 (5)
F23	0.0560 (7)	0.0436 (6)	0.0289 (5)	0.0129 (5)	−0.0043 (5)	−0.0021 (4)
F24	0.0491 (6)	0.0280 (5)	0.0430 (6)	−0.0061 (4)	0.0157 (5)	0.0048 (4)
F25	0.0448 (6)	0.0420 (6)	0.0368 (5)	0.0005 (5)	0.0203 (4)	−0.0061 (4)
F26	0.0459 (6)	0.0406 (6)	0.0407 (6)	0.0037 (4)	0.0231 (5)	0.0007 (4)

Geometric parameters (Å, º)

N1—C12	1.483 (2)	C12—H12A	0.9800
N1—C11	1.493 (2)	C12—H12B	0.9800
N1—C2	1.508 (2)	C12—H12C	0.9800
N1—H1	0.88 (2)	C41—H41A	0.9800
C2—C3	1.515 (2)	C41—H41B	0.9800
C2—H2A	0.9900	C41—H41C	0.9800
C2—H2B	0.9900	C71—H71A	0.9800
C3—N4	1.4769 (18)	C71—H71B	0.9800
C3—H3A	0.9900	C71—H71C	0.9800
C3—H3B	0.9900	C72—H72A	0.9800
N4—C41	1.466 (2)	C72—H72B	0.9800
N4—C5	1.4736 (18)	C72—H72C	0.9800
C5—C6	1.522 (2)	P1—F11	1.5842 (13)
C5—H5A	0.9900	P1—F14	1.5874 (11)
C5—H5B	0.9900	P1—F15	1.5957 (11)
C6—N7	1.5010 (19)	P1—F13	1.5987 (12)
C6—H6A	0.9900	P1—F12	1.6062 (12)
C6—H6B	0.9900	P1—F16	1.6262 (10)
N7—C72	1.492 (2)	P2—F24	1.5989 (10)
N7—C71	1.4967 (19)	P2—F22	1.6026 (11)
N7—H7	0.853 (19)	P2—F23	1.6029 (11)
C11—H11A	0.9800	P2—F26	1.6050 (10)
C11—H11B	0.9800	P2—F25	1.6055 (10)
C11—H11C	0.9800	P2—F21	1.6087 (11)
C12—N1—C11	111.17 (15)	H12B—C12—H12C	109.5
C12—N1—C2	114.09 (14)	N4—C41—H41A	109.5
C11—N1—C2	109.38 (13)	N4—C41—H41B	109.5
C12—N1—H1	106.6 (13)	H41A—C41—H41B	109.5
C11—N1—H1	107.5 (13)	N4—C41—H41C	109.5
C2—N1—H1	107.9 (13)	H41A—C41—H41C	109.5
N1—C2—C3	111.54 (12)	H41B—C41—H41C	109.5
N1—C2—H2A	109.3	N7—C71—H71A	109.5
C3—C2—H2A	109.3	N7—C71—H71B	109.5
N1—C2—H2B	109.3	H71A—C71—H71B	109.5
C3—C2—H2B	109.3	N7—C71—H71C	109.5
H2A—C2—H2B	108.0	H71A—C71—H71C	109.5
N4—C3—C2	111.86 (13)	H71B—C71—H71C	109.5
N4—C3—H3A	109.2	N7—C72—H72A	109.5
C2—C3—H3A	109.2	N7—C72—H72B	109.5
N4—C3—H3B	109.2	H72A—C72—H72B	109.5
C2—C3—H3B	109.2	N7—C72—H72C	109.5
H3A—C3—H3B	107.9	H72A—C72—H72C	109.5
C41—N4—C5	110.47 (13)	H72B—C72—H72C	109.5
C41—N4—C3	111.33 (13)	F11—P1—F14	90.95 (8)
C5—N4—C3	109.57 (12)	F11—P1—F15	91.38 (7)
N4—C5—C6	112.09 (12)	F14—P1—F15	91.13 (7)
N4—C5—H5A	109.2	F11—P1—F13	90.00 (8)
C6—C5—H5A	109.2	F14—P1—F13	178.36 (7)
N4—C5—H5B	109.2	F15—P1—F13	90.19 (7)
C6—C5—H5B	109.2	F11—P1—F12	178.56 (7)
H5A—C5—H5B	107.9	F14—P1—F12	89.24 (7)
N7—C6—C5	112.17 (12)	F15—P1—F12	90.04 (7)
N7—C6—H6A	109.2	F13—P1—F12	89.78 (8)
C5—C6—H6A	109.2	F11—P1—F16	89.89 (6)
N7—C6—H6B	109.2	F14—P1—F16	89.66 (6)
C5—C6—H6B	109.2	F15—P1—F16	178.49 (8)
H6A—C6—H6B	107.9	F13—P1—F16	89.01 (6)
C72—N7—C71	110.63 (13)	F12—P1—F16	88.68 (6)
C72—N7—C6	113.31 (12)	F24—P2—F22	90.57 (7)
C71—N7—C6	110.74 (12)	F24—P2—F23	89.66 (6)
C72—N7—H7	106.2 (12)	F22—P2—F23	179.75 (8)
C71—N7—H7	107.4 (12)	F24—P2—F26	89.90 (6)
C6—N7—H7	108.3 (13)	F22—P2—F26	89.98 (6)
N1—C11—H11A	109.5	F23—P2—F26	89.92 (6)
N1—C11—H11B	109.5	F24—P2—F25	90.50 (6)
H11A—C11—H11B	109.5	F22—P2—F25	89.59 (6)
N1—C11—H11C	109.5	F23—P2—F25	90.50 (6)
H11A—C11—H11C	109.5	F26—P2—F25	179.41 (7)
H11B—C11—H11C	109.5	F24—P2—F21	178.68 (7)
N1—C12—H12A	109.5	F22—P2—F21	90.75 (7)
N1—C12—H12B	109.5	F23—P2—F21	89.02 (7)
H12A—C12—H12B	109.5	F26—P2—F21	90.08 (6)
N1—C12—H12C	109.5	F25—P2—F21	89.53 (6)
H12A—C12—H12C	109.5
C12—N1—C2—C3	68.23 (18)	C41—N4—C5—C6	−74.07 (17)
C11—N1—C2—C3	−166.55 (14)	C3—N4—C5—C6	162.91 (13)
N1—C2—C3—N4	52.69 (18)	N4—C5—C6—N7	−52.33 (17)
C2—C3—N4—C41	72.43 (17)	C5—C6—N7—C72	−58.80 (17)
C2—C3—N4—C5	−165.07 (13)	C5—C6—N7—C71	176.21 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F16	0.88 (2)	2.18 (2)	2.9590 (16)	146.4 (18)
N1—H1···F12	0.88 (2)	2.49 (2)	3.1482 (18)	131.5 (16)
N7—H7···F16	0.853 (19)	2.209 (19)	2.9502 (16)	145.2 (17)
N7—H7···F13	0.853 (19)	2.395 (19)	3.0883 (17)	138.9 (15)