Acetyl-ene-ammonia-18-crown-6 (1/2/1).

The title compound, C(2)H(2)·C(12)H(24)O(6)·2NH(3), was formed by co-crystallization of 18-crown-6 and acetyl-ene in liquid ammonia. The 18-crown-6 mol-ecule has threefold rotoinversion symmetry. The acteylene mol-ecule lies on the threefold axis and the whole mol-ecule is generated by an inversion center. The two ammonia mol-ecules are also located on the threefold axis and are related by inversion symmetry. In the crystal, the ammonia mol-ecules are located below and above the crown ether plane and are connected by inter-molecular N-H⋯O hydrogen bonds. The acetyl-ene mol-ecules are additionally linked by weak C-H⋯N inter-actions into chains that propagate in the direction of the crystallographic c axis. The 18-crown-6 mol-ecule [occupancy ratio 0.830 (4):0.170 (4)] is disordered and was refined using a split model.

Related literature

For weak inter­molecular inter­actions such as hydrogen bonds and their application in crystal engineering, see: Desiraju (2002 ▶, 2007 ▶); Boese et al. (2003 ▶, 2009 ▶); Kirchner et al. (2004 ▶); Steiner (2002 ▶)

Experimental

Crystal data

C2H2·C12H24O6·2NH3

M = 324.42

Trigonal,

a = 11.8915 (1) Å

c = 11.5736 (2) Å

V = 1417.33 (3) Å3

Z = 3

Cu Kα radiation

μ = 0.73 mm−1

T = 123 K

0.1 × 0.1 × 0.1 mm

Data collection

Oxford Diffraction SuperNova diffractometer

Absorption correction: analytical [CrysAlis PRO (Agilent, 2012 ▶), based on expressions derived by Clark & Reid (1995 ▶)] T min = 0.798, T max = 0.841

5835 measured reflections

640 independent reflections

598 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.11

640 reflections

53 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: olex2.solve (Bourhis et al., 2012 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, H, 2011 ▶); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812038792/nc2288sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038792/nc2288Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038792/nc2288Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812038792/nc2288Isup4.cml

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

C2H2·C12H24O6·2NH3	Dx = 1.140 Mg m−3
Mr = 324.42	Cu Kα radiation, λ = 1.54184 Å
Trigonal, R3	Cell parameters from 3585 reflections
Hall symbol: -R 3	θ = 5.8–73.3°
a = 11.8915 (1) Å	µ = 0.73 mm−1
c = 11.5736 (2) Å	T = 123 K
V = 1417.33 (3) Å3	Block, clear colourless
Z = 3	0.1 × 0.1 × 0.1 mm
F(000) = 534

Oxford Diffraction SuperNova diffractometer	640 independent reflections
Radiation source: fine-focus sealed tube	598 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 73.3°, θmin = 5.8°
Absorption correction: analytical [CrysAlis PRO (Agilent, 2012), based on expressions derived by Clark & Reid (1995)]	h = −14→14
Tmin = 0.798, Tmax = 0.841	k = −14→14
5835 measured reflections	l = −14→14

Refinement on F2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.8298P] where P = (Fo2 + 2Fc2)/3
640 reflections	(Δ/σ)max < 0.001
53 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. Absorption correction: Crysalis Pro, Agilent Technologies, Version 1.171.35.21, Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R. C. Clark & J. S. Reid (1995).Crystal mounting in perfluorether

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.34988 (11)	0.43774 (10)	0.64475 (7)	0.0298 (4)	0.830 (4)
C2	0.23519 (11)	0.32279 (10)	0.67833 (11)	0.0387 (4)
H2AA	0.2314	0.3164	0.7637	0.046*	0.830 (4)
H2AB	0.2375	0.2463	0.6476	0.046*	0.830 (4)
H2BC	0.1912	0.2473	0.7309	0.046*	0.170 (4)
H2BD	0.2225	0.2880	0.5987	0.046*	0.170 (4)
C3	0.46325 (13)	0.45185 (13)	0.69816 (12)	0.0344 (4)	0.830 (4)
H3B	0.4711	0.3743	0.6819	0.041*	0.830 (4)
H3A	0.4568	0.4586	0.7829	0.041*	0.830 (4)
O1A	0.4390 (5)	0.5013 (5)	0.6463 (3)	0.0254 (17)	0.170 (4)
C3A	0.3587 (6)	0.3803 (6)	0.7006 (6)	0.0312 (12)	0.17
H3AB	0.3905	0.3206	0.6786	0.037*	0.170 (4)
H3AA	0.3700	0.3934	0.7852	0.037*	0.170 (4)
N1	0.3333	0.6667	0.50242 (13)	0.0330 (4)
H1A	0.3430	0.6046	0.5340	0.040*
C1	0.3333	0.6667	0.21796 (16)	0.0289 (4)
H1	0.3333	0.6667	0.3000	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0306 (8)	0.0310 (6)	0.0287 (5)	0.0160 (5)	0.0010 (4)	0.0042 (4)
C2	0.0397 (7)	0.0276 (6)	0.0487 (7)	0.0168 (5)	0.0111 (5)	0.0046 (4)
C3	0.0379 (8)	0.0347 (7)	0.0359 (8)	0.0220 (7)	−0.0045 (5)	−0.0002 (5)
O1A	0.027 (3)	0.029 (3)	0.022 (2)	0.016 (2)	−0.0035 (16)	0.0004 (17)
C3A	0.027 (3)	0.029 (3)	0.040 (3)	0.016 (3)	−0.002 (2)	0.000 (3)
N1	0.0363 (6)	0.0363 (6)	0.0263 (7)	0.0182 (3)	0.000	0.000
C1	0.0257 (5)	0.0257 (5)	0.0351 (8)	0.0129 (3)	0.000	0.000

O1—C2	1.4196 (15)	C3—H3B	0.9900
O1—C3	1.4148 (18)	C3—H3A	0.9900
C2—H2AA	0.9900	O1A—C2ii	1.446 (5)
C2—H2AB	0.9900	O1A—C3A	1.416 (8)
C2—H2BC	0.9900	C3A—H3AB	0.9900
C2—H2BD	0.9900	C3A—H3AA	0.9900
C2—C3i	1.4698 (18)	N1—H1A	0.8810
C2—O1Ai	1.446 (5)	C1—C1iii	1.187 (4)
C2—C3A	1.298 (6)	C1—H1	0.9500
C3—C2ii	1.4698 (18)
C3—O1—C2	113.22 (10)	C3A—C2—H2BC	107.5
O1—C2—H2AA	109.4	C3A—C2—H2BD	107.5
O1—C2—H2AB	109.4	C3A—C2—C3i	152.4 (3)
O1—C2—H2BC	149.2	C3A—C2—O1Ai	119.3 (3)
O1—C2—H2BD	91.2	O1—C3—C2ii	110.55 (11)
O1—C2—C3i	111.27 (10)	O1—C3—H3B	109.5
O1—C2—O1Ai	89.71 (18)	O1—C3—H3A	109.5
H2AA—C2—H2AB	108.0	C2ii—C3—H3B	109.5
H2BC—C2—H2BD	107.0	C2ii—C3—H3A	109.5
C3i—C2—H2AA	109.4	H3B—C3—H3A	108.1
C3i—C2—H2AB	109.4	C3A—O1A—C2ii	122.5 (4)
C3i—C2—H2BC	97.7	C2—C3A—O1A	117.3 (5)
C3i—C2—H2BD	74.6	C2—C3A—H3AB	108.0
O1Ai—C2—H2AA	87.6	C2—C3A—H3AA	108.0
O1Ai—C2—H2AB	148.6	O1A—C3A—H3AB	108.0
O1Ai—C2—H2BC	107.5	O1A—C3A—H3AA	108.0
O1Ai—C2—H2BD	107.5	H3AB—C3A—H3AA	107.2
C3A—C2—H2AA	80.7	C1iii—C1—H1	180.0
C3A—C2—H2AB	90.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	2.40	3.2709 (12)	171
N1—H1A···O1A	0.88	2.43	3.270 (4)	159
C1—H1···N1	0.95	2.34	3.292 (2)	180

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.88	2.40	3.2709 (12)	171
N1—H1A⋯O1A	0.88	2.43	3.270 (4)	159
C1—H1⋯N1	0.95	2.34	3.292 (2)	180