1-Hexyl-1,3,6,8-tetra-aza-tricyclo-[4.3.1.1]undecan-1-ium iodide.

In the title compound, C(13)H(27)N(4) (+)·I(-), the ethyl-ene bridge is distorted from the ideal D(2d) symmetry wherein an N-C-C-N planar bridge, around whose C-C bond the C-N and C-H bonds are exactly eclipsed, is disordered over two sites with equal occupancies. In both disorder components, the hexyl chain adopts an ideal all-trans conformation. In the crystal, adjacent ions are connected by C-H⋯I hydrogen bonds, forming ionic pairs that are further linked into chains along [101] via a second C-H⋯I inter-action.

Related literature

For related structures, see: Rivera et al. (2011a ▶,b ▶). For the preparation of the title compound, see: Rivera et al. (2011b ▶). For synthetic applications of quaternary ammonium salts, see: Starks (1971 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C13H27N4 +·I−

M = 366.3

Monoclinic,

a = 8.4914 (4) Å

b = 16.1497 (6) Å

c = 11.8673 (6) Å

β = 102.690 (5)°

V = 1587.65 (13) Å3

Z = 4

Mo Kα radiation

μ = 2.01 mm−1

T = 120 K

0.21 × 0.19 × 0.11 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶), T min = 0.930, T max = 1.000

6803 measured reflections

6795 independent reflections

4959 reflections with I > 3σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.086

S = 1.23

6795 reflections

160 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.71 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811050781/bx2384sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050781/bx2384Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050781/bx2384Isup3.cml

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

C13H27N4+·I−	F(000) = 744
Mr = 366.3	Dx = 1.532 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 6021 reflections
a = 8.4914 (4) Å	θ = 3.0–28.6°
b = 16.1497 (6) Å	µ = 2.01 mm−1
c = 11.8673 (6) Å	T = 120 K
β = 102.690 (5)°	Prism, colourless
V = 1587.65 (13) Å3	0.21 × 0.19 × 0.11 mm
Z = 4

Agilent Xcalibur Atlas Gemini ultra diffractometer	6795 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4959 reflections with I > 3σ(I)
graphite	Rint = 0.028
Detector resolution: 10.3784 pixels mm-1	θmax = 28.7°, θmin = 2.8°
Rotation method data acquisition using ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010),	k = −21→21
Tmin = 0.930, Tmax = 1.000	l = −15→15
6803 measured reflections

Refinement on F2	126 constraints
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.086	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
S = 1.23	(Δ/σ)max = 0.010
6795 reflections	Δρmax = 0.71 e Å−3
160 parameters	Δρmin = −0.54 e Å−3
6 restraints

Experimental. (CrysAlis PRO; Agilent, 2010), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F2 for refinement carried out on F and F2, respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.76438 (2)	0.145638 (12)	0.653063 (18)	0.03486 (7)
N1	0.3333 (2)	0.14856 (13)	0.3771 (2)	0.0243 (7)
N2	0.1997 (3)	0.08915 (14)	0.5186 (2)	0.0288 (8)
N3	0.0378 (3)	0.14480 (14)	0.3388 (2)	0.0315 (8)
N4	0.2240 (3)	0.23902 (15)	0.5091 (2)	0.0388 (9)
C1	0.3335 (3)	0.07917 (16)	0.4647 (2)	0.0271 (9)
C2	0.0478 (3)	0.08342 (17)	0.4302 (2)	0.0304 (9)
C3	0.3437 (3)	0.23048 (16)	0.4446 (2)	0.0305 (10)
C4	0.1724 (3)	0.14102 (17)	0.2875 (2)	0.0264 (8)
C5	−0.0374 (8)	0.2221 (3)	0.3446 (7)	0.0496 (12)*	0.5
C5x	0.0024 (9)	0.2269 (3)	0.3739 (7)	0.0496 (12)*	0.5
C6	0.0726 (7)	0.2638 (5)	0.4366 (6)	0.0572 (13)*	0.5
C6x	0.0779 (8)	0.2814 (5)	0.4655 (7)	0.0572 (13)*	0.5
C7	0.2155 (4)	0.16748 (18)	0.5817 (3)	0.0362 (11)
C8	0.4742 (3)	0.14364 (17)	0.3199 (3)	0.0311 (9)
C9	0.4960 (4)	0.0633 (2)	0.2612 (3)	0.0442 (12)
C10	0.6358 (4)	0.0646 (2)	0.2041 (3)	0.0449 (12)
C11	0.6715 (4)	−0.0158 (2)	0.1516 (3)	0.0431 (12)
C12	0.8106 (4)	−0.0173 (2)	0.0927 (3)	0.0597 (15)
C13	0.8456 (4)	−0.0991 (2)	0.0453 (3)	0.0559 (15)
H1a	0.325427	0.026624	0.426054	0.0325*
H1b	0.432326	0.080962	0.522431	0.0325*
H2a	0.037822	0.028919	0.397084	0.0365*
H2b	−0.042195	0.090043	0.46622	0.0365*
H3a	0.448482	0.23527	0.495002	0.0366*
H3b	0.337177	0.276138	0.391924	0.0366*
H4a	0.165088	0.184457	0.231378	0.0317*
H4b	0.170457	0.089787	0.246222	0.0317*
H5b	−0.043281	0.251622	0.273587	0.0596*	0.5
H5ax	−0.045388	0.258903	0.306961	0.0596*	0.5
H5bx	−0.112446	0.234851	0.357854	0.0596*	0.5
H6a	0.012618	0.295738	0.481032	0.0686*	0.5
H6b	0.07684	0.321573	0.418284	0.0686*	0.5
H6ax	0.014906	0.283059	0.523445	0.0686*	0.5
H6bx	0.100532	0.3335	0.433464	0.0686*	0.5
H7a	0.30989	0.165774	0.643444	0.0435*
H7b	0.126368	0.173803	0.618669	0.0435*
H8a	0.571696	0.15691	0.375121	0.0373*
H8b	0.468506	0.188379	0.265919	0.0373*
H9a	0.509646	0.0191	0.316598	0.053*
H9b	0.399214	0.05054	0.205088	0.053*
H10a	0.730382	0.083252	0.258209	0.0539*
H10b	0.619781	0.107199	0.146302	0.0539*
H11a	0.576002	−0.035328	0.099259	0.0517*
H11b	0.685421	−0.058664	0.20906	0.0517*
H12a	0.905875	0.002829	0.144747	0.0716*
H12b	0.793601	0.02334	0.032196	0.0716*
H13a	0.930204	−0.092887	0.003967	0.0839*
H13b	0.879025	−0.137625	0.107581	0.0839*
H13c	0.750077	−0.119484	−0.00617	0.0839*
H5a	−0.13884	0.213923	0.366185	0.0596*	0.5

	U11	U22	U33	U12	U13	U23
I1	0.02999 (10)	0.03331 (11)	0.03983 (12)	0.00062 (9)	0.00452 (8)	−0.01420 (10)
N1	0.0220 (11)	0.0227 (11)	0.0273 (12)	−0.0016 (10)	0.0034 (9)	0.0020 (10)
N2	0.0321 (12)	0.0270 (12)	0.0271 (14)	−0.0009 (10)	0.0056 (11)	0.0047 (10)
N3	0.0240 (11)	0.0380 (14)	0.0308 (14)	−0.0042 (11)	0.0024 (10)	0.0098 (12)
N4	0.0467 (15)	0.0317 (14)	0.0413 (17)	−0.0010 (13)	0.0168 (13)	−0.0035 (12)
C1	0.0270 (14)	0.0235 (14)	0.0285 (16)	0.0001 (11)	0.0012 (12)	0.0065 (12)
C2	0.0273 (14)	0.0336 (16)	0.0294 (16)	−0.0070 (13)	0.0045 (12)	0.0046 (13)
C3	0.0344 (15)	0.0219 (14)	0.0328 (17)	−0.0062 (12)	0.0022 (14)	0.0006 (12)
C4	0.0233 (12)	0.0310 (15)	0.0217 (14)	−0.0036 (12)	−0.0022 (11)	0.0059 (13)
C7	0.0433 (18)	0.0391 (17)	0.0265 (17)	−0.0058 (14)	0.0083 (14)	−0.0017 (13)
C8	0.0247 (13)	0.0323 (15)	0.0372 (17)	−0.0053 (13)	0.0087 (12)	0.0051 (14)
C9	0.0467 (19)	0.0394 (18)	0.052 (2)	−0.0038 (15)	0.0230 (17)	−0.0022 (16)
C10	0.0341 (16)	0.0442 (19)	0.058 (2)	−0.0009 (16)	0.0135 (16)	0.0005 (17)
C11	0.0455 (19)	0.0450 (19)	0.041 (2)	0.0046 (15)	0.0145 (17)	0.0044 (16)
C12	0.042 (2)	0.059 (2)	0.083 (3)	−0.0058 (18)	0.026 (2)	−0.012 (2)
C13	0.050 (2)	0.073 (3)	0.048 (2)	0.018 (2)	0.0190 (19)	0.000 (2)

N1—C1	1.529 (4)	C5x—H5ax	0.96
N1—C3	1.539 (3)	C5x—H5bx	0.96
N1—C4	1.541 (3)	C6—H6a	0.96
N1—C8	1.502 (4)	C6—H6b	0.96
N2—C1	1.430 (4)	C6x—H6ax	0.96
N2—C2	1.476 (3)	C6x—H6bx	0.96
N2—C7	1.461 (4)	C7—H7a	0.96
N3—C2	1.458 (4)	C7—H7b	0.96
N3—C4	1.409 (4)	C8—C9	1.503 (4)
N3—C5	1.411 (6)	C8—H8a	0.96
N3—C5x	1.441 (6)	C8—H8b	0.96
N4—C3	1.408 (4)	C9—C10	1.490 (5)
N4—C6	1.438 (7)	C9—H9a	0.96
N4—C6x	1.412 (7)	C9—H9b	0.96
N4—C7	1.452 (4)	C10—C11	1.500 (5)
C1—H1a	0.96	C10—H10a	0.96
C1—H1b	0.96	C10—H10b	0.96
C2—H2a	0.96	C11—C12	1.499 (5)
C2—H2b	0.96	C11—H11a	0.96
C3—H3a	0.96	C11—H11b	0.96
C3—H3b	0.96	C12—C13	1.491 (6)
C4—H4a	0.96	C12—H12a	0.96
C4—H4b	0.96	C12—H12b	0.96
C5—C6	1.439 (10)	C13—H13a	0.96
C5—H5b	0.96	C13—H13b	0.96
C5—H5a	0.96	C13—H13c	0.96
C5x—C6x	1.435 (10)
C1—N1—C3	106.5 (2)	N4—C6—C5	132.1 (6)
C1—N1—C4	106.25 (19)	N4—C6—H6a	109.4707
C1—N1—C8	112.7 (2)	N4—C6—H6b	109.4714
C3—N1—C4	111.58 (19)	C5—C6—H6a	109.4715
C3—N1—C8	108.7 (2)	C5—C6—H6b	109.4717
C4—N1—C8	111.0 (2)	H6a—C6—H6b	69.7221
C1—N2—C2	109.3 (2)	N4—C6x—C5x	101.0 (6)
C1—N2—C7	109.5 (2)	N4—C6x—H6ax	109.4706
C2—N2—C7	112.7 (2)	N4—C6x—H6bx	109.4714
C2—N3—C4	111.8 (2)	C5x—C6x—H6ax	109.4706
C2—N3—C5	121.2 (4)	C5x—C6x—H6bx	109.4716
C2—N3—C5x	113.1 (4)	H6ax—C6x—H6bx	116.7784
C4—N3—C5	118.6 (4)	N2—C7—N4	113.3 (3)
C4—N3—C5x	113.9 (4)	N2—C7—H7a	109.4714
C3—N4—C6	111.0 (4)	N2—C7—H7b	109.472
C3—N4—C6x	121.9 (4)	N4—C7—H7a	109.4709
C3—N4—C7	112.4 (2)	N4—C7—H7b	109.4705
C6—N4—C7	115.0 (4)	H7a—C7—H7b	105.3282
C6x—N4—C7	116.7 (4)	N1—C8—C9	116.5 (2)
N1—C1—N2	109.8 (2)	N1—C8—H8a	109.4716
N1—C1—H1a	109.4711	N1—C8—H8b	109.4713
N1—C1—H1b	109.4708	C9—C8—H8a	109.4715
N2—C1—H1a	109.4712	C9—C8—H8b	109.4708
N2—C1—H1b	109.4718	H8a—C8—H8b	101.3702
H1a—C1—H1b	109.0907	C8—C9—C10	113.0 (3)
N2—C2—N3	112.6 (2)	C8—C9—H9a	109.4702
N2—C2—H2a	109.4708	C8—C9—H9b	109.4711
N2—C2—H2b	109.472	C10—C9—H9a	109.472
N3—C2—H2a	109.4708	C10—C9—H9b	109.4714
N3—C2—H2b	109.4711	H9a—C9—H9b	105.7374
H2a—C2—H2b	106.0941	C9—C10—C11	115.5 (3)
N1—C3—N4	113.7 (2)	C9—C10—H10a	109.4709
N1—C3—H3a	109.4712	C9—C10—H10b	109.471
N1—C3—H3b	109.4711	C11—C10—H10a	109.4711
N4—C3—H3a	109.4713	C11—C10—H10b	109.4722
N4—C3—H3b	109.4714	H10a—C10—H10b	102.6643
H3a—C3—H3b	104.9048	C10—C11—C12	117.3 (3)
N1—C4—N3	112.3 (2)	C10—C11—H11a	109.4708
N1—C4—H4a	109.4714	C10—C11—H11b	109.4718
N1—C4—H4b	109.4716	C12—C11—H11a	109.4709
N3—C4—H4a	109.471	C12—C11—H11b	109.4715
N3—C4—H4b	109.4715	H11a—C11—H11b	100.2535
H4a—C4—H4b	106.513	C11—C12—C13	115.6 (3)
N3—C5—C6	103.0 (5)	C11—C12—H12a	109.4712
N3—C5—H5b	109.4716	C11—C12—H12b	109.4718
N3—C5—H5a	109.472	C13—C12—H12a	109.4714
C6—C5—H5b	109.4704	C13—C12—H12b	109.4707
C6—C5—H5a	109.4707	H12a—C12—H12b	102.5339
H5b—C5—H5a	115.2131	C12—C13—H13a	109.4716
N3—C5x—C6x	134.1 (6)	C12—C13—H13b	109.471
N3—C5x—H5ax	109.4707	C12—C13—H13c	109.4712
N3—C5x—H5bx	109.471	H13a—C13—H13b	109.4712
C6x—C5x—H5ax	109.4709	H13a—C13—H13c	109.4704
C6x—C5x—H5bx	109.4719	H13b—C13—H13c	109.4719
H5ax—C5x—H5bx	62.4606
?—?—?—?	?

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1a···I1i	0.96	2.98	3.913 (3)	164
C3—H3b···I1ii	0.96	3.04	3.925 (2)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1a⋯I1i	0.96	2.98	3.913 (3)	164
C3—H3b⋯I1ii	0.96	3.04	3.925 (2)	154

Symmetry codes: (i) ; (ii) .