(2S,7S)-10-Ethyl-1,8,10,12-tetra-aza-tetra-cyclo-[8.3.1.1(8,12).0(2,7)]penta-decan-10-ium iodide.

The title chiral quaternary ammonium salt, C(13)H(25)N(4) (+)·I(-), was synthesized through the Menschutkin reaction between the cage aminal (2S,7S)-1,8,10,12-tetra-aza-tetra-cyclo-[8.3.1.1(8,12).0(2,7)]penta-decane and ethyl iodide. The quaternization occurred regioselectively on the nitrogen with major sp3 character. The crystal structure consists of anions and cations separated by normal distances. Ions are not linked through C-H⋯I hydrogen bonds.

Related literature

For related structures, see: Becka et al. (1963 ▶); Rivera et al. (2011b ▶,c ▶); Rivera, Sadat-Bernal et al. (2012 ▶). For the synthesis of the precursor (2S,7S)-1,8,10,12-n class="Species">tetra­aza­tetra­cyclo [8.3.1.18,12.02,7]penta­decane, see: Rivera, Quiroga et al. (2012 ▶). For the preparation of the title salt, see: Rivera et al. (2011a ▶). For bond-length data, see: Allen et al. (1987 ▶). For the structural consequences of the anomeric effect, see: Kakanejadifard & Farnia (1997 ▶); Rivera et al. (2011b ▶). For synthetic applications of chiral quaternary ammonium salts, see: Lygo Andrews (2004 ▶); Park et al. (2004 ▶); Kim & Huh (2001 ▶).

Experimental

Crystal data

C13H25N4 +·I−

M = 364.3

Orthorhombic,

a = 10.2227 (5) Å

b = 12.0375 (6) Å

c = 12.0941 (6) Å

V = 1488.25 (13) Å3

Z = 4

Mo Kα radiation

μ = 2.14 mm−1

T = 120 K

0.24 × 0.06 × 0.04 mm

Data collection

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.746, T max = 1

5935 measured reflections

3223 independent reflections

3093 reflections with I > 3σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.017

wR(F 2) = 0.041

S = 1.19

3223 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 1353 Friedel pairs

Flack parameter: 0.026 (15)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: Superflip (Palatinus & Chapuis, 2007 ▶); 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/S1600536812040159/bh2451sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040159/bh2451Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812040159/bh2451Isup3.cml

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

C13H25N4+·I−	Dx = 1.625 Mg m−3
Mr = 364.3	Melting point: 450 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3457 reflections
a = 10.2227 (5) Å	θ = 3.1–27.0°
b = 12.0375 (6) Å	µ = 2.14 mm−1
c = 12.0941 (6) Å	T = 120 K
V = 1488.25 (13) Å3	Prism, colourless
Z = 4	0.24 × 0.06 × 0.04 mm
F(000) = 736

Agilent Xcalibur (Atlas, Gemini ultra) diffractometer	3223 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3093 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 10.3784 pixels mm-1	θmax = 27.1°, θmin = 3.1°
ω scans	h = −13→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→15
Tmin = 0.746, Tmax = 1	l = −10→15
5935 measured reflections

Refinement on F2	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.017	Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2)
wR(F2) = 0.041	(Δ/σ)max = 0.018
S = 1.19	Δρmax = 0.23 e Å−3
3223 reflections	Δρmin = −0.47 e Å−3
164 parameters	Absolute structure: Flack (1983), 1353 Friedel pairs
0 restraints	Flack parameter: 0.026 (15)
0 constraints

	x	y	z	Uiso*/Ueq
I1	0.995575 (12)	0.462386 (9)	0.966324 (9)	0.01806 (4)
C1	0.4852 (2)	0.29285 (13)	0.73421 (15)	0.0153 (5)
N2	0.36266 (17)	0.33495 (15)	0.78149 (16)	0.0157 (5)
C3	0.2959 (2)	0.26756 (17)	0.86111 (18)	0.0170 (6)
N4	0.20151 (16)	0.17701 (14)	0.81134 (14)	0.0141 (5)
C5	0.2742 (2)	0.08504 (16)	0.74916 (17)	0.0146 (6)
N6	0.35735 (17)	0.12860 (15)	0.66504 (15)	0.0148 (5)
C7	0.4840 (2)	0.16841 (14)	0.70831 (15)	0.0142 (5)
C8	0.6008 (2)	0.13825 (18)	0.63737 (19)	0.0198 (7)
C9	0.7262 (2)	0.16905 (18)	0.6984 (2)	0.0213 (7)
C10	0.7278 (2)	0.28974 (16)	0.73715 (19)	0.0212 (7)
C11	0.6056 (2)	0.31806 (19)	0.8036 (2)	0.0180 (6)
C12	0.2718 (2)	0.37477 (18)	0.69715 (19)	0.0211 (6)
N13	0.19918 (17)	0.28513 (15)	0.64344 (16)	0.0194 (5)
C14	0.2834 (2)	0.20109 (17)	0.58957 (18)	0.0191 (6)
C15	0.1162 (2)	0.23336 (18)	0.72399 (18)	0.0186 (6)
C16	0.1232 (2)	0.13179 (17)	0.90618 (18)	0.0203 (6)
C17	0.0267 (2)	0.04169 (19)	0.87726 (19)	0.0289 (7)
H1c1	0.490912	0.333228	0.66593	0.0183*
H1c3	0.247872	0.314369	0.91096	0.0204*
H2c3	0.358654	0.232404	0.908641	0.0204*
H1c5	0.325356	0.042413	0.80047	0.0175*
H2c5	0.212023	0.035003	0.716646	0.0175*
H1c7	0.493127	0.128663	0.776687	0.017*
H1c8	0.600074	0.059842	0.62289	0.0237*
H2c8	0.596557	0.178345	0.568841	0.0237*
H1c9	0.800126	0.155718	0.651276	0.0256*
H2c9	0.737333	0.120781	0.760916	0.0256*
H1c10	0.804004	0.302556	0.781695	0.0254*
H2c10	0.733483	0.338024	0.674158	0.0254*
H1c11	0.606624	0.395538	0.822422	0.0216*
H2c11	0.603662	0.274033	0.869799	0.0216*
H1c12	0.211459	0.426301	0.729818	0.0254*
H2c12	0.319	0.416333	0.642393	0.0254*
H1c14	0.23152	0.156343	0.540652	0.0229*
H2c14	0.342843	0.237356	0.539822	0.0229*
H1c15	0.062251	0.178719	0.688439	0.0224*
H2c15	0.062416	0.288707	0.7586	0.0224*
H1c16	0.078397	0.191556	0.9426	0.0243*
H2c16	0.181437	0.105459	0.962693	0.0243*
H1c17	−0.019759	0.019483	0.942586	0.0346*
H2c17	−0.034168	0.069235	0.823415	0.0346*
H3c17	0.072673	−0.021042	0.847344	0.0346*

	U11	U22	U33	U12	U13	U23
I1	0.01928 (7)	0.01921 (7)	0.01568 (7)	0.00180 (7)	0.00111 (8)	0.00244 (4)
C1	0.0163 (11)	0.0137 (9)	0.0159 (8)	−0.0011 (8)	−0.0006 (11)	−0.0009 (7)
N2	0.0173 (9)	0.0108 (9)	0.0188 (10)	0.0020 (7)	0.0016 (8)	0.0008 (8)
C3	0.0184 (10)	0.0152 (10)	0.0174 (10)	0.0000 (8)	0.0010 (9)	−0.0024 (8)
N4	0.0139 (9)	0.0150 (9)	0.0133 (8)	−0.0001 (7)	0.0012 (8)	0.0007 (7)
C5	0.0180 (10)	0.0118 (10)	0.0140 (10)	−0.0001 (8)	0.0006 (9)	−0.0012 (8)
N6	0.0158 (9)	0.0147 (9)	0.0138 (9)	−0.0025 (7)	−0.0021 (8)	0.0006 (7)
C7	0.0168 (11)	0.0124 (8)	0.0132 (8)	−0.0004 (9)	−0.0006 (10)	0.0005 (7)
C8	0.0216 (11)	0.0155 (11)	0.0222 (12)	−0.0011 (9)	0.0048 (10)	−0.0031 (9)
C9	0.0167 (11)	0.0211 (12)	0.0260 (12)	0.0019 (9)	0.0039 (10)	−0.0022 (10)
C10	0.0165 (11)	0.0212 (12)	0.0257 (12)	−0.0032 (8)	−0.0022 (10)	−0.0010 (10)
C11	0.0203 (11)	0.0150 (11)	0.0187 (11)	−0.0033 (9)	0.0002 (10)	−0.0007 (9)
C12	0.0218 (11)	0.0143 (11)	0.0274 (11)	0.0025 (9)	0.0003 (10)	0.0061 (9)
N13	0.0180 (9)	0.0201 (9)	0.0200 (9)	0.0011 (7)	−0.0001 (8)	0.0059 (7)
C14	0.0218 (11)	0.0234 (11)	0.0121 (10)	−0.0023 (9)	−0.0013 (9)	0.0027 (9)
C15	0.0147 (11)	0.0216 (11)	0.0196 (11)	0.0034 (8)	−0.0044 (9)	0.0028 (9)
C16	0.0206 (11)	0.0254 (12)	0.0148 (10)	−0.0005 (9)	0.0045 (9)	0.0005 (9)
C17	0.0255 (12)	0.0346 (12)	0.0265 (11)	−0.0074 (11)	0.0048 (10)	0.0037 (9)

C1—C7	1.530 (2)	C9—H2c9	0.96
C1—C11	1.521 (3)	C10—C9	1.527 (3)
C1—H1c1	0.96	C10—C11	1.524 (3)
N2—C1	1.467 (3)	C10—H1c10	0.96
N2—C3	1.432 (3)	C10—H2c10	0.96
N2—C12	1.460 (3)	C11—H1c11	0.96
C3—H1c3	0.96	C11—H2c11	0.96
C3—H2c3	0.96	C12—H1c12	0.96
N4—C3	1.575 (3)	C12—H2c12	0.96
N4—C5	1.531 (3)	N13—C12	1.462 (3)
N4—C15	1.529 (3)	N13—C14	1.480 (3)
N4—C16	1.501 (3)	N13—C15	1.434 (3)
C5—H1c5	0.96	C14—H1c14	0.96
C5—H2c5	0.96	C14—H2c14	0.96
N6—C5	1.426 (3)	C15—H1c15	0.96
N6—C7	1.476 (3)	C15—H2c15	0.96
N6—C14	1.472 (3)	C16—H1c16	0.96
C7—H1c7	0.96	C16—H2c16	0.96
C8—C7	1.514 (3)	C17—C16	1.507 (3)
C8—C9	1.526 (3)	C17—H1c17	0.96
C8—H1c8	0.96	C17—H2c17	0.96
C8—H2c8	0.96	C17—H3c17	0.96
C9—H1c9	0.96
N2—C1—C7	114.27 (17)	H1c9—C9—H2c9	105.87
N2—C1—C11	114.02 (16)	C9—C10—H1c10	109.47
N2—C1—H1c1	102.26	C9—C10—H2c10	109.47
C7—C1—C11	108.35 (17)	C11—C10—C9	111.49 (18)
C7—C1—H1c1	108.66	C11—C10—H1c10	109.47
C11—C1—H1c1	108.95	C11—C10—H2c10	109.47
C1—N2—C3	118.26 (16)	H1c10—C10—H2c10	107.37
C1—N2—C12	112.59 (17)	C1—C11—C10	109.11 (18)
C12—N2—C3	110.62 (17)	C1—C11—H1c11	109.47
N2—C3—N4	115.28 (17)	C1—C11—H2c11	109.47
N2—C3—H1c3	109.47	C10—C11—H1c11	109.47
N2—C3—H2c3	109.47	C10—C11—H2c11	109.47
N4—C3—H1c3	109.47	H1c11—C11—H2c11	109.83
N4—C3—H2c3	109.47	N2—C12—N13	113.02 (17)
H1c3—C3—H2c3	102.97	N2—C12—H1c12	109.47
C3—N4—C5	113.01 (15)	N2—C12—H2c12	109.47
C3—N4—C15	107.85 (15)	N13—C12—H1c12	109.47
C3—N4—C16	106.58 (15)	N13—C12—H2c12	109.47
C5—N4—C15	104.97 (15)	H1c12—C12—H2c12	105.67
C16—N4—C5	111.84 (15)	C12—N13—C14	113.87 (17)
C16—N4—C15	112.64 (15)	C12—N13—C15	108.62 (17)
N4—C5—H1c5	109.47	C14—N13—C15	110.25 (17)
N4—C5—H2c5	109.47	N6—C14—N13	115.54 (18)
N6—C5—N4	111.96 (16)	N6—C14—H1c14	109.47
N6—C5—H1c5	109.47	N6—C14—H2c14	109.47
N6—C5—H2c5	109.47	N13—C14—H1c14	109.47
H1c5—C5—H2c5	106.87	N13—C14—H2c14	109.47
C7—N6—C5	112.91 (16)	H1c14—C14—H2c14	102.63
C7—N6—C14	118.54 (16)	N4—C15—H1c15	109.47
C14—N6—C5	110.77 (16)	N4—C15—H2c15	109.47
C1—C7—H1c7	108.1	N13—C15—N4	108.96 (17)
N6—C7—C1	113.40 (17)	N13—C15—H1c15	109.47
N6—C7—C8	114.37 (16)	N13—C15—H2c15	109.47
N6—C7—H1c7	103.22	H1c15—C15—H2c15	109.98
C8—C7—C1	110.15 (17)	N4—C16—C17	115.63 (18)
C8—C7—H1c7	106.98	N4—C16—H1c16	109.47
C7—C8—C9	109.28 (18)	N4—C16—H2c16	109.47
C7—C8—H1c8	109.47	C17—C16—H1c16	109.47
C7—C8—H2c8	109.47	C17—C16—H2c16	109.47
C9—C8—H1c8	109.47	H1c16—C16—H2c16	102.52
C9—C8—H2c8	109.47	C16—C17—H1c17	109.47
H1c8—C8—H2c8	109.66	C16—C17—H2c17	109.47
C8—C9—C10	112.85 (18)	C16—C17—H3c17	109.47
C8—C9—H1c9	109.47	H1c17—C17—H2c17	109.47
C8—C9—H2c9	109.47	H1c17—C17—H3c17	109.47
C10—C9—H1c9	109.47	H2c17—C17—H3c17	109.47
C10—C9—H2c9	109.47