Hydrogen bonding in N,N,N',N'-tetra­methyl­ethyl­ene­di­ammonium bis­(benzene­selenol­ate)

The crystal structure of the title compound, [Me₂NHC₂H₄NHMe₂][SePh]₂ or C₆H₁₈N₂²⁺·2C₆H₅Se^-, reveals hydrogen bonding between the benzene­seleno­late anions and the tetra­methyl­ethyl­ene­di­ammonium cations. The asymmetric unit contains one formula unit of the title compound. The two Se...H distances are 2.22 (4) and 2.34 (4) Å.

Computing details

Data collection: CAD-4 Operations Manual (Enraf-Nonius, 1977); cell refinement: CAD-4 Operations Manual; data reduction: PROCESS in MolEN (Fair, 1990); program(s) used to solve structure: MULTAN80 (Main et al., 1980); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: CIF VAX in MolEN.

(I)

Crystal data

C6H18N2^2+·2C6H5Se^−	F(000) = 872
Mr = 430.36	Dx = 1.46 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 10 reflections
a = 11.542 (4) Å	θ = 10–14°
b = 11.246 (5) Å	µ = 3.78 mm^−1
c = 15.641 (5) Å	T = 294 K
β = 105.43 (3)°	Plate, colourless
V = 1957 (2) Å^3	0.25 × 0.15 × 0.05 mm
Z = 4

Data collection

Enraf–Nonius CAD-4 diffractometer	Rint = 0.071
θ/θ scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: empirical (using intensity measurements) via ψ scans (North et al., 1968)	h = 0→14
Tmin = 0.381, Tmax = 0.828	k = 0→13
4396 measured reflections	l = −19→18
3845 independent reflections	3 standard reflections every 50 min
2768 reflections with I > 2σ(I)	intensity decay: 6.9%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	All H-atom parameters refined
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0517P)^2] where P = (Fo^2 + 2Fc^2)/3
3845 reflections	(Δ/σ)max = 0.001
311 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.71 e Å^−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
Se1	0.43183 (3)	0.21798 (3)	0.32408 (3)	0.03386 (12)
Se2	0.04759 (3)	0.75782 (3)	0.40451 (3)	0.03087 (11)
N1	0.2191 (2)	0.5330 (2)	0.48145 (19)	0.0255 (6)
N2	0.2816 (2)	0.4564 (2)	0.26221 (19)	0.0260 (6)
C1	0.3304 (3)	0.1679 (3)	0.2120 (2)	0.0282 (7)
C2	0.3578 (3)	0.1929 (3)	0.1334 (3)	0.0358 (8)
C3	0.2807 (4)	0.1615 (4)	0.0527 (3)	0.0492 (11)
C4	0.1744 (4)	0.1035 (4)	0.0489 (3)	0.0454 (10)
C5	0.1468 (3)	0.0768 (3)	0.1264 (3)	0.0401 (9)
C6	0.2235 (3)	0.1083 (3)	0.2068 (3)	0.0334 (8)
C7	0.0224 (3)	0.7289 (3)	0.2807 (2)	0.0270 (7)
C8	0.0943 (3)	0.7825 (3)	0.2324 (3)	0.0352 (8)
C9	0.0756 (4)	0.7623 (3)	0.1436 (3)	0.0410 (9)
C10	−0.0159 (3)	0.6883 (3)	0.0981 (3)	0.0413 (9)
C11	−0.0881 (3)	0.6347 (3)	0.1449 (3)	0.0408 (10)
C12	−0.0683 (3)	0.6542 (3)	0.2343 (3)	0.0340 (9)
C13	0.1599 (3)	0.4607 (3)	0.5369 (3)	0.0332 (8)
C14	0.3286 (3)	0.5929 (4)	0.5363 (3)	0.0358 (9)
C15	0.2391 (3)	0.4574 (3)	0.4085 (2)	0.0302 (8)
C16	0.2796 (3)	0.5310 (3)	0.3410 (2)	0.0302 (8)
C17	0.1607 (3)	0.4220 (4)	0.2071 (3)	0.0353 (8)
C18	0.3507 (4)	0.5195 (4)	0.2089 (3)	0.0415 (9)
H19	0.326 (3)	0.383 (4)	0.285 (3)	0.047 (11)*
H20	0.168 (3)	0.594 (4)	0.456 (3)	0.048 (12)*
H2	0.424 (3)	0.226 (3)	0.135 (3)	0.035 (10)*
H3	0.298 (3)	0.175 (4)	0.006 (3)	0.047 (12)*
H4	0.118 (3)	0.085 (4)	−0.005 (3)	0.047 (12)*
H5	0.071 (4)	0.036 (4)	0.124 (3)	0.058 (12)*
H6	0.204 (3)	0.093 (3)	0.256 (2)	0.032 (10)*
H8	0.153 (3)	0.824 (3)	0.267 (2)	0.033 (10)*
H9	0.128 (3)	0.798 (3)	0.112 (3)	0.048 (11)*
H10	−0.029 (3)	0.672 (3)	0.036 (3)	0.043 (11)*
H11	−0.142 (3)	0.588 (3)	0.119 (3)	0.038 (11)*
H12	−0.112 (3)	0.622 (3)	0.263 (3)	0.037 (11)*
H13A	0.217 (3)	0.401 (3)	0.565 (3)	0.042 (10)*
H13B	0.088 (4)	0.419 (4)	0.493 (3)	0.050 (11)*
H13C	0.131 (3)	0.516 (4)	0.579 (3)	0.050 (11)*
H14A	0.376 (3)	0.535 (3)	0.559 (3)	0.036 (11)*
H14B	0.297 (3)	0.642 (3)	0.579 (2)	0.018 (8)*
H14C	0.363 (3)	0.638 (3)	0.502 (2)	0.036 (10)*
H15B	0.160 (4)	0.420 (4)	0.378 (3)	0.064 (13)*
H15A	0.299 (3)	0.389 (4)	0.439 (3)	0.046 (11)*
H16A	0.227 (3)	0.604 (3)	0.319 (2)	0.018 (8)*
H16B	0.364 (3)	0.564 (3)	0.364 (3)	0.044 (11)*
H17A	0.113 (3)	0.498 (4)	0.180 (3)	0.049 (11)*
H17B	0.116 (3)	0.370 (4)	0.240 (3)	0.048 (11)*
H17C	0.167 (3)	0.380 (3)	0.158 (2)	0.031 (10)*
H18A	0.358 (3)	0.467 (3)	0.159 (2)	0.033 (10)*
H18B	0.318 (3)	0.592 (4)	0.191 (3)	0.047 (12)*
H18C	0.434 (4)	0.533 (4)	0.247 (3)	0.056 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.03015 (18)	0.0300 (2)	0.0376 (2)	0.00862 (13)	0.00232 (15)	−0.00097 (16)
Se2	0.02664 (18)	0.02632 (18)	0.0401 (2)	0.00488 (12)	0.00966 (15)	0.00008 (15)
N1	0.0273 (14)	0.0235 (14)	0.0255 (17)	0.0047 (11)	0.0070 (12)	−0.0004 (12)
N2	0.0258 (14)	0.0232 (14)	0.0296 (17)	0.0024 (10)	0.0086 (12)	−0.0004 (12)
C1	0.0278 (16)	0.0226 (16)	0.034 (2)	0.0084 (12)	0.0071 (14)	0.0063 (14)
C2	0.0304 (19)	0.038 (2)	0.041 (2)	0.0048 (15)	0.0128 (17)	0.0082 (17)
C3	0.062 (3)	0.058 (3)	0.031 (3)	0.011 (2)	0.018 (2)	0.014 (2)
C4	0.043 (2)	0.044 (2)	0.041 (3)	0.0077 (17)	−0.003 (2)	−0.0010 (19)
C5	0.0335 (19)	0.038 (2)	0.046 (3)	−0.0001 (16)	0.0064 (18)	−0.0015 (18)
C6	0.0350 (19)	0.0306 (19)	0.036 (2)	0.0043 (14)	0.0130 (18)	0.0059 (16)
C7	0.0236 (15)	0.0195 (15)	0.037 (2)	0.0066 (12)	0.0054 (14)	0.0062 (14)
C8	0.0343 (19)	0.0270 (18)	0.046 (3)	−0.0021 (14)	0.0138 (17)	0.0024 (17)
C9	0.049 (2)	0.032 (2)	0.047 (3)	0.0056 (16)	0.022 (2)	0.0083 (18)
C10	0.047 (2)	0.034 (2)	0.039 (2)	0.0133 (16)	0.0047 (19)	0.0022 (18)
C11	0.0265 (19)	0.036 (2)	0.053 (3)	0.0014 (15)	−0.0012 (18)	−0.0044 (19)
C12	0.0222 (17)	0.0268 (18)	0.052 (3)	−0.0003 (13)	0.0080 (17)	0.0020 (17)
C13	0.0254 (18)	0.0323 (19)	0.042 (2)	0.0030 (14)	0.0094 (17)	0.0050 (17)
C14	0.0281 (19)	0.036 (2)	0.041 (2)	−0.0063 (16)	0.0057 (18)	0.0007 (18)
C15	0.0311 (18)	0.0235 (17)	0.037 (2)	0.0008 (13)	0.0102 (16)	−0.0034 (15)
C16	0.0331 (18)	0.0241 (17)	0.035 (2)	−0.0025 (14)	0.0128 (16)	−0.0034 (15)
C17	0.0249 (17)	0.040 (2)	0.038 (2)	−0.0005 (15)	0.0033 (16)	−0.0004 (19)
C18	0.048 (2)	0.032 (2)	0.049 (3)	−0.0051 (17)	0.021 (2)	0.0022 (19)

Geometric parameters (Å, º)

Se1—C1	1.916 (4)	C9—C10	1.384 (6)
Se2—C7	1.909 (4)	C9—H9	0.96 (4)
N1—C13	1.481 (4)	C10—C11	1.384 (6)
N1—C14	1.487 (4)	C10—H10	0.96 (4)
N1—C15	1.490 (4)	C11—C12	1.372 (6)
N1—H20	0.92 (4)	C11—H11	0.83 (4)
N2—C18	1.478 (4)	C12—H12	0.84 (4)
N2—C17	1.484 (4)	C13—H13A	0.96 (4)
N2—C16	1.497 (4)	C13—H13B	1.03 (4)
N2—H19	0.99 (4)	C13—H13C	1.03 (4)
C1—C2	1.378 (5)	C14—H14A	0.86 (4)
C1—C6	1.387 (5)	C14—H14B	1.02 (3)
C2—C3	1.383 (6)	C14—H14C	0.90 (4)
C2—H2	0.84 (4)	C15—C16	1.510 (5)
C3—C4	1.376 (6)	C15—H15B	1.00 (4)
C3—H3	0.82 (4)	C15—H15A	1.06 (4)
C4—C5	1.365 (6)	C16—H16A	1.03 (3)
C4—H4	0.94 (4)	C16—H16B	1.01 (4)
C5—C6	1.378 (5)	C17—H17A	1.04 (4)
C5—H5	0.99 (4)	C17—H17B	1.00 (4)
C6—H6	0.87 (4)	C17—H17C	0.92 (4)
C7—C12	1.387 (5)	C18—H18A	1.00 (4)
C7—C8	1.398 (5)	C18—H18B	0.91 (4)
C8—C9	1.366 (6)	C18—H18C	1.00 (4)
C8—H8	0.88 (4)
C13—N1—C14	111.4 (3)	C12—C11—C10	120.6 (4)
C13—N1—C15	108.9 (3)	C12—C11—H11	120 (3)
C14—N1—C15	114.8 (3)	C10—C11—H11	119 (3)
C13—N1—H20	109 (2)	C11—C12—C7	121.8 (4)
C14—N1—H20	105 (2)	C11—C12—H12	121 (3)
C15—N1—H20	108 (2)	C7—C12—H12	117 (3)
C18—N2—C17	111.3 (3)	N1—C13—H13A	106 (2)
C18—N2—C16	108.9 (3)	N1—C13—H13B	106 (2)
C17—N2—C16	114.0 (3)	H13A—C13—H13B	108 (3)
C18—N2—H19	108 (2)	N1—C13—H13C	109 (2)
C17—N2—H19	108 (2)	H13A—C13—H13C	116 (3)
C16—N2—H19	107 (2)	H13B—C13—H13C	111 (3)
C2—C1—C6	117.3 (4)	N1—C14—H14A	104 (2)
C2—C1—Se1	121.8 (3)	N1—C14—H14B	103.2 (17)
C6—C1—Se1	120.9 (3)	H14A—C14—H14B	116 (3)
C1—C2—C3	121.1 (4)	N1—C14—H14C	111 (2)
C1—C2—H2	119 (3)	H14A—C14—H14C	109 (3)
C3—C2—H2	120 (3)	H14B—C14—H14C	112 (3)
C4—C3—C2	120.7 (4)	N1—C15—C16	111.2 (3)
C4—C3—H3	118 (3)	N1—C15—H15B	108 (3)
C2—C3—H3	121 (3)	C16—C15—H15B	108 (3)
C5—C4—C3	118.8 (4)	N1—C15—H15A	107 (2)
C5—C4—H4	118 (2)	C16—C15—H15A	115 (2)
C3—C4—H4	123 (2)	H15B—C15—H15A	108 (3)
C4—C5—C6	120.6 (4)	N2—C16—C15	110.1 (3)
C4—C5—H5	119 (3)	N2—C16—H16A	108.2 (18)
C6—C5—H5	120 (3)	C15—C16—H16A	114.2 (17)
C5—C6—C1	121.5 (4)	N2—C16—H16B	106 (2)
C5—C6—H6	120 (2)	C15—C16—H16B	113 (2)
C1—C6—H6	119 (2)	H16A—C16—H16B	104 (3)
C12—C7—C8	116.9 (4)	N2—C17—H17A	109 (2)
C12—C7—Se2	121.6 (3)	N2—C17—H17B	113 (2)
C8—C7—Se2	121.5 (3)	H17A—C17—H17B	114 (3)
C9—C8—C7	121.4 (4)	N2—C17—H17C	110 (2)
C9—C8—H8	127 (2)	H17A—C17—H17C	103 (3)
C7—C8—H8	112 (2)	H17B—C17—H17C	106 (3)
C8—C9—C10	121.0 (4)	N2—C18—H18A	109 (2)
C8—C9—H9	120 (2)	N2—C18—H18B	111 (2)
C10—C9—H9	119 (2)	H18A—C18—H18B	113 (3)
C9—C10—C11	118.3 (4)	N2—C18—H18C	108 (2)
C9—C10—H10	122 (2)	H18A—C18—H18C	107 (3)
C11—C10—H10	120 (2)	H18B—C18—H18C	108 (3)