3,14-Diethyl-2,13-di­aza-6,17-diazonia­tri­cyclo­[16.4.0.07,12]docosane dichloride tetra­hydrate from synchrotron radiation

Moon, D.; Subhan, M.A.; Choi, J.-H.

doi:10.1107/S1600536813027232

organic compounds

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Volume 69| Part 11| November 2013| Page o1620

doi:10.1107/S1600536813027232

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3,14-Diethyl-2,13-diaza-6,17-diazoniatricyclo[16.4.0.0^7,12]docosane dichloride tetrahydrate from synchrotron radiation

Dohyun Moon,^a Md Abdus Subhan ^b and Jong-Ha Choi ^c ^*

^aPohang Accelerator Laboratory, POSTECH, Pohang 790-784, Republic of Korea, ^bDepartment of Chemistry, Shah Jalal University of Science and Technology, Sylhet, Bangladesh, and ^cDepartment of Chemistry, Andong National University, Andong 760-749, Republic of Korea
^*Correspondence e-mail: jhchoi@andong.ac.kr

(Received 2 October 2013; accepted 3 October 2013; online 9 October 2013)

The asymmetric unit of title hydrated salt, C₂₂H₄₆N₄²⁺·2Cl⁻·4H₂O, comprises half a centrosymmetric dication, one Cl⁻ anion and two water molecules of crystallization. The structure determination reveals that protonation has occurred at diagonally opposite amine N atoms, and that the dication features intramolecular N—H⋯N hydrogen bonds. In the crystal, a three-dimensional artchitecture is formed by O—H⋯Cl/N and N—H⋯Cl/O hydrogen bonds.

CCDC reference: 891186

Related literature

For background to the coordination chemistry of tetraazamacrocycles, see: Choi et al. (2010 ); De Clercq (2010 ). For the synthesis of the precursor macrocycle, see: Lim et al. (2006 ). For related structures, see: Choi et al. (2006 , 2011 ).

Experimental

Crystal data

C₂₂H₄₆N₄²⁺·2Cl⁻·4H₂O
M_r = 509.59
Monoclinic, C 2/c
a = 22.122 (4) Å
b = 13.616 (3) Å
c = 10.565 (2) Å
β = 115.23 (3)°
V = 2878.5 (10) Å³
Z = 4
Synchrotron radiation
λ = 0.72000 Å
μ = 0.27 mm⁻¹
T = 95 K
0.31 × 0.28 × 0.25 mm

Data collection

ADSC Q210 CCD area-detector diffractometer
Absorption correction: empirical (using intensity measurements) (HKL-3000 SCALEPACK; Otwinowski & Minor, 1997 ) T_min = 0.922, T_max = 0.937
13046 measured reflections
3663 independent reflections
3446 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.079
S = 1.05
3663 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯Cl1	0.909 (13)	2.182 (14)	3.0900 (9)	177.3 (12)
N1—H2N1⋯N2ⁱ	0.907 (13)	2.200 (13)	2.9348 (11)	137.6 (10)
N2—H1N2⋯O1Wⁱⁱ	0.887 (13)	2.262 (13)	3.1242 (12)	164.1 (11)
O1W—H1O1⋯Cl1	0.833 (19)	2.400 (19)	3.2329 (14)	178.6 (17)
O1W—H2O1⋯Cl1ⁱⁱⁱ	0.820 (18)	2.335 (18)	3.1479 (10)	171.1 (15)
O2W—H1O2⋯O1W^iv	0.84 (2)	2.06 (2)	2.9021 (15)	178.1 (18)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983 ); cell refinement: HKL3000sm (Otwinowski & Minor, 1997); data reduction: HKL3000sm; program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013; molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 891186

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813027232/tk5261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813027232/tk5261Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813027232/tk5261Isup3.cml

checkCIF report

Comment top

The coordination chemistry of tetraazamacrocycles with steric hindrance on the macrocyclic ring, and their complexes are of interest because of their various applications (Choi et al., 2010). Recently, the constrained cyclam derivatives have been reported to exhibit anti-HIV effects and to stimulate the activity of stem cells from the bone marrow (De Clercq, 2010).

The title compound, Fig. 1, containing a positively charged macrocycle, Cl^- and water molecules was characterized during the studies of di-N-substituted macrocyclic ligands as well as their corresponding copper(II) complexes. The macrocylic ligand lies on a center-of-inversion. Thus, the asymmetric unit contains half of a macrocylic dication, one chloride anion and two water molecules. The four N atoms are coplanar, and the ethyl substituents are anti with respect to the macrocyclic plane as a result of the symmetry of the molecule. The C—C and C—N lengths and associated angles are in the normal range (Choi et al., 2006, 2011). As expected, the N–C distances involving the protonated nitrogen atom, N1 are slightly longer than the other N–C distances. The cyclohexane ring that is fused to the 14-membered ring exists in a stable chair conformation, and the N1—C2—C3—N2 torsion angle displays a gauche conformation. The crystal structure is stabilized by different types of hydrogen bonds, Table 1.

Related literature top

For background to the coordination chemistry of tetraazamacrocycles, see: Choi et al. (2010); De Clercq (2010). For the synthesis of the precursor macrocycle, see: Lim et al. (2006). For related structures, see: Choi et al. (2006, 2011).

Experimental top

The starting material, the macrocycle 3,14-diethyl-2,6,13,17-tetraazatricyclo(16.4.0.0^7,12)docosane (L) was prepared according to published procedure (Lim et al., 2006). L (0.67 g, 0.2 mmol) was taken in a round bottomed flask in EtOH (10 ml). 2-Chloro-N,N-diethylacetamide (0.0936 g, 0.5 mmol) in EtOH (5 ml) was added. Then triethylamine (1.33 g, 0.2 mmol) in EtOH (2 ml) was added. The mixture was heated to reflux for 24 h. Colourless crystals suitable for X-ray analysis were obtained from the solution at 298 K over a period of a few days.

Computing details top

Data collection: PAL ADSC Quantum-210 ADX (Arvai & Nielsen, 1983); cell refinement: HKL3000sm (Otwinowski & Minor, 1997); data reduction: HKL3000sm (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXL2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

Fig. 1. The molecular structure of title compound with displacements ellipsoids drawn at the 50% probability level for non-H atoms. Primed atoms are related by the symmetry operation 1/2-x, 1/2-y, 1-z.

3,14-Diethyl-2,13-diaza-6,17-diazoniatricyclo[16.4.0.0^7,12]docosane dichloride tetrahydrate top

Crystal data top

C₂₂H₄₆N₄²⁺·2Cl⁻·4H₂O	F(000) = 1120
M_r = 509.59	D_x = 1.176 Mg m⁻³
Monoclinic, C2/c	Synchrotron radiation, λ = 0.72000 Å
a = 22.122 (4) Å	Cell parameters from 31113 reflections
b = 13.616 (3) Å	θ = 1.3–66.4°
c = 10.565 (2) Å	µ = 0.27 mm⁻¹
β = 115.23 (3)°	T = 95 K
V = 2878.5 (10) Å³	Block, colourless
Z = 4	0.31 × 0.28 × 0.25 mm

Data collection top

ADSC Q210 CCD area-detector diffractometer	3663 independent reflections
Radiation source: PLSII 2D bending magnet	3446 reflections with I > 2σ(I)
Si(111) double crystal monochromator	R_int = 0.028
ω scan	θ_max = 29.0°, θ_min = 1.8°
Absorption correction: empirical (using intensity measurements) (HKL-3000 SCALEPACK; Otwinowski & Minor, 1997)	h = −29→29
T_min = 0.922, T_max = 0.937	k = −18→18
13046 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0412P)² + 2.157P] where P = (F_o² + 2F_c²)/3
3663 reflections	(Δ/σ)_max < 0.001
178 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₂H₄₆N₄²⁺·2Cl⁻·4H₂O	V = 2878.5 (10) Å³
M_r = 509.59	Z = 4
Monoclinic, C2/c	Synchrotron radiation, λ = 0.72000 Å
a = 22.122 (4) Å	µ = 0.27 mm⁻¹
b = 13.616 (3) Å	T = 95 K
c = 10.565 (2) Å	0.31 × 0.28 × 0.25 mm
β = 115.23 (3)°

Data collection top

ADSC Q210 CCD area-detector diffractometer	3663 independent reflections
Absorption correction: empirical (using intensity measurements) (HKL-3000 SCALEPACK; Otwinowski & Minor, 1997)	3446 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.937	R_int = 0.028
13046 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.46 e Å⁻³
3663 reflections	Δρ_min = −0.35 e Å⁻³
178 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.24338 (3)	0.30241 (5)	0.30460 (7)	0.00545 (13)
H1N1	0.2484 (6)	0.3678 (10)	0.3234 (13)	0.013 (3)*
H2N1	0.2370 (6)	0.2756 (9)	0.3766 (13)	0.014 (3)*
N2	0.34493 (3)	0.23871 (5)	0.55886 (7)	0.00584 (14)
H1N2	0.3460 (6)	0.1738 (10)	0.5533 (13)	0.012 (3)*
C1	0.18207 (4)	0.28405 (6)	0.17163 (8)	0.00738 (15)
H1A	0.1831	0.2160	0.1398	0.009*
H1B	0.1819	0.3293	0.0981	0.009*
C2	0.30641 (4)	0.26138 (6)	0.30527 (8)	0.00612 (15)
H2	0.3004	0.1891	0.2872	0.007*
C3	0.32229 (4)	0.30822 (7)	0.19167 (8)	0.01049 (16)
H3A	0.3289	0.3798	0.2083	0.013*
H3B	0.2844	0.2980	0.0990	0.013*
C4	0.38574 (4)	0.26195 (8)	0.19333 (9)	0.01451 (18)
H4A	0.3775	0.1916	0.1680	0.017*
H4B	0.3971	0.2947	0.1226	0.017*
C5	0.44453 (4)	0.27145 (8)	0.33736 (9)	0.01465 (18)
H5A	0.4836	0.2358	0.3377	0.018*
H5B	0.4569	0.3415	0.3572	0.018*
C6	0.42661 (4)	0.22968 (7)	0.45105 (9)	0.01216 (17)
H6A	0.4645	0.2403	0.5436	0.015*
H6B	0.4194	0.1580	0.4370	0.015*
C7	0.36367 (4)	0.27744 (6)	0.44987 (8)	0.00632 (15)
H7	0.3718	0.3497	0.4651	0.008*
C8	0.39051 (4)	0.27036 (6)	0.70259 (8)	0.00656 (15)
H8	0.4375	0.2635	0.7134	0.008*
C9	0.38146 (4)	0.20090 (6)	0.80803 (8)	0.00776 (15)
H9A	0.3820	0.1324	0.7770	0.009*
H9B	0.4203	0.2089	0.8998	0.009*
C10	0.37854 (4)	0.37876 (6)	0.72406 (9)	0.01032 (16)
H10A	0.3825	0.4182	0.6492	0.012*
H10B	0.3324	0.3865	0.7153	0.012*
C11	0.42749 (5)	0.41859 (7)	0.86611 (10)	0.01776 (19)
H11A	0.4227	0.3815	0.9408	0.027*
H11B	0.4179	0.4881	0.8734	0.027*
H11C	0.4733	0.4117	0.8753	0.027*
Cl1	0.256487 (11)	0.526092 (15)	0.35905 (2)	0.01378 (8)
O1W	0.16965 (4)	0.51673 (5)	0.02378 (8)	0.01737 (15)
H1O1	0.1926 (9)	0.5195 (12)	0.110 (2)	0.038 (4)*
H2O1	0.1952 (8)	0.5022 (12)	−0.0111 (17)	0.033 (4)*
O2W	0.52804 (5)	0.02912 (8)	0.40229 (12)	0.0354 (2)
H1O2	0.5693 (11)	0.0172 (13)	0.4382 (19)	0.044 (5)*
H2O2	0.512 (2)	0.016 (3)	0.328 (5)	0.062 (14)*	0.50
H3O2	0.5140 (19)	0.015 (3)	0.457 (4)	0.041 (10)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0030 (3)	0.0080 (3)	0.0048 (3)	−0.0006 (2)	0.0011 (2)	−0.0001 (2)
N2	0.0045 (3)	0.0083 (3)	0.0045 (3)	−0.0011 (2)	0.0017 (2)	−0.0001 (2)
C1	0.0037 (3)	0.0124 (4)	0.0044 (3)	−0.0012 (3)	0.0001 (3)	0.0005 (3)
C2	0.0030 (3)	0.0095 (3)	0.0061 (3)	0.0000 (3)	0.0021 (3)	−0.0009 (3)
C3	0.0072 (4)	0.0190 (4)	0.0057 (3)	−0.0013 (3)	0.0032 (3)	0.0007 (3)
C4	0.0084 (4)	0.0291 (5)	0.0080 (4)	−0.0005 (3)	0.0054 (3)	−0.0023 (3)
C5	0.0058 (4)	0.0308 (5)	0.0093 (4)	−0.0008 (3)	0.0050 (3)	−0.0001 (3)
C6	0.0050 (3)	0.0232 (4)	0.0093 (4)	0.0032 (3)	0.0040 (3)	0.0019 (3)
C7	0.0032 (3)	0.0109 (4)	0.0049 (3)	−0.0011 (3)	0.0018 (3)	0.0000 (3)
C8	0.0036 (3)	0.0099 (4)	0.0053 (3)	−0.0008 (3)	0.0010 (3)	−0.0002 (3)
C9	0.0041 (3)	0.0111 (4)	0.0069 (3)	0.0010 (3)	0.0012 (3)	0.0023 (3)
C10	0.0131 (4)	0.0091 (4)	0.0081 (3)	−0.0011 (3)	0.0039 (3)	−0.0007 (3)
C11	0.0209 (5)	0.0151 (4)	0.0129 (4)	−0.0049 (4)	0.0030 (3)	−0.0055 (3)
Cl1	0.01970 (12)	0.00834 (11)	0.01508 (12)	−0.00076 (7)	0.00912 (9)	0.00064 (7)
O1W	0.0187 (3)	0.0182 (3)	0.0168 (3)	0.0023 (3)	0.0092 (3)	0.0010 (3)
O2W	0.0226 (5)	0.0488 (6)	0.0330 (5)	0.0101 (4)	0.0101 (4)	0.0081 (4)

Geometric parameters (Å, º) top

N1—C2	1.4995 (10)	C6—C7	1.5320 (11)
N1—C1	1.5003 (12)	C6—H6A	0.9900
N1—H1N1	0.909 (13)	C6—H6B	0.9900
N1—H2N1	0.907 (13)	C7—H7	1.0000
N2—C7	1.4774 (10)	C8—C10	1.5333 (12)
N2—C8	1.4842 (11)	C8—C9	1.5381 (11)
N2—H1N2	0.887 (13)	C8—H8	1.0000
C1—C9ⁱ	1.5234 (11)	C9—C1ⁱ	1.5233 (11)
C1—H1A	0.9900	C9—H9A	0.9900
C1—H1B	0.9900	C9—H9B	0.9900
C2—C3	1.5264 (11)	C10—C11	1.5276 (13)
C2—C7	1.5285 (12)	C10—H10A	0.9900
C2—H2	1.0000	C10—H10B	0.9900
C3—C4	1.5318 (12)	C11—H11A	0.9800
C3—H3A	0.9900	C11—H11B	0.9800
C3—H3B	0.9900	C11—H11C	0.9800
C4—C5	1.5286 (13)	O1W—H1O1	0.833 (19)
C4—H4A	0.9900	O1W—H2O1	0.820 (18)
C4—H4B	0.9900	O2W—H1O2	0.84 (2)
C5—C6	1.5262 (12)	O2W—H2O2	0.73 (4)
C5—H5A	0.9900	O2W—H3O2	0.78 (4)
C5—H5B	0.9900

C2—N1—C1	114.20 (6)	C5—C6—H6A	109.2
C2—N1—H1N1	109.7 (8)	C7—C6—H6A	109.2
C1—N1—H1N1	110.2 (8)	C5—C6—H6B	109.2
C2—N1—H2N1	108.8 (8)	C7—C6—H6B	109.2
C1—N1—H2N1	108.5 (8)	H6A—C6—H6B	107.9
H1N1—N1—H2N1	105.0 (11)	N2—C7—C2	109.85 (6)
C7—N2—C8	113.56 (6)	N2—C7—C6	113.46 (7)
C7—N2—H1N2	106.2 (8)	C2—C7—C6	108.08 (7)
C8—N2—H1N2	109.4 (8)	N2—C7—H7	108.4
N1—C1—C9ⁱ	111.44 (7)	C2—C7—H7	108.4
N1—C1—H1A	109.3	C6—C7—H7	108.4
C9ⁱ—C1—H1A	109.3	N2—C8—C10	110.24 (6)
N1—C1—H1B	109.3	N2—C8—C9	108.72 (6)
C9ⁱ—C1—H1B	109.3	C10—C8—C9	113.61 (7)
H1A—C1—H1B	108.0	N2—C8—H8	108.0
N1—C2—C3	111.46 (7)	C10—C8—H8	108.0
N1—C2—C7	108.91 (7)	C9—C8—H8	108.0
C3—C2—C7	110.83 (7)	C1ⁱ—C9—C8	115.61 (7)
N1—C2—H2	108.5	C1ⁱ—C9—H9A	108.4
C3—C2—H2	108.5	C8—C9—H9A	108.4
C7—C2—H2	108.5	C1ⁱ—C9—H9B	108.4
C2—C3—C4	109.63 (7)	C8—C9—H9B	108.4
C2—C3—H3A	109.7	H9A—C9—H9B	107.4
C4—C3—H3A	109.7	C11—C10—C8	113.10 (7)
C2—C3—H3B	109.7	C11—C10—H10A	109.0
C4—C3—H3B	109.7	C8—C10—H10A	109.0
H3A—C3—H3B	108.2	C11—C10—H10B	109.0
C5—C4—C3	111.30 (7)	C8—C10—H10B	109.0
C5—C4—H4A	109.4	H10A—C10—H10B	107.8
C3—C4—H4A	109.4	C10—C11—H11A	109.5
C5—C4—H4B	109.4	C10—C11—H11B	109.5
C3—C4—H4B	109.4	H11A—C11—H11B	109.5
H4A—C4—H4B	108.0	C10—C11—H11C	109.5
C6—C5—C4	110.83 (7)	H11A—C11—H11C	109.5
C6—C5—H5A	109.5	H11B—C11—H11C	109.5
C4—C5—H5A	109.5	H1O1—O1W—H2O1	106.6 (16)
C6—C5—H5B	109.5	H1O2—O2W—H2O2	111 (4)
C4—C5—H5B	109.5	H1O2—O2W—H3O2	108 (3)
H5A—C5—H5B	108.1	H2O2—O2W—H3O2	124 (5)
C5—C6—C7	112.06 (7)

C2—N1—C1—C9ⁱ	162.93 (7)	C3—C2—C7—N2	175.38 (6)
C1—N1—C2—C3	62.08 (9)	N1—C2—C7—C6	176.69 (7)
C1—N1—C2—C7	−175.33 (6)	C3—C2—C7—C6	−60.34 (9)
N1—C2—C3—C4	−178.28 (7)	C5—C6—C7—N2	−179.94 (7)
C7—C2—C3—C4	60.24 (9)	C5—C6—C7—C2	57.97 (9)
C2—C3—C4—C5	−56.36 (10)	C7—N2—C8—C10	73.59 (8)
C3—C4—C5—C6	54.06 (11)	C7—N2—C8—C9	−161.26 (6)
C4—C5—C6—C7	−55.52 (11)	N2—C8—C9—C1ⁱ	−75.02 (9)
C8—N2—C7—C2	−167.13 (6)	C10—C8—C9—C1ⁱ	48.13 (9)
C8—N2—C7—C6	71.78 (9)	N2—C8—C10—C11	−175.53 (7)
N1—C2—C7—N2	52.42 (8)	C9—C8—C10—C11	62.15 (9)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···Cl1	0.909 (13)	2.182 (14)	3.0900 (9)	177.3 (12)
N1—H2N1···N2ⁱ	0.907 (13)	2.200 (13)	2.9348 (11)	137.6 (10)
N2—H1N2···O1Wⁱⁱ	0.887 (13)	2.262 (13)	3.1242 (12)	164.1 (11)
O1W—H1O1···Cl1	0.833 (19)	2.400 (19)	3.2329 (14)	178.6 (17)
O1W—H2O1···Cl1ⁱⁱⁱ	0.820 (18)	2.335 (18)	3.1479 (10)	171.1 (15)
O2W—H1O2···O1W^iv	0.84 (2)	2.06 (2)	2.9021 (15)	178.1 (18)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, −y+1, z−1/2; (iv) x+1/2, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···Cl1	0.909 (13)	2.182 (14)	3.0900 (9)	177.3 (12)
N1—H2N1···N2ⁱ	0.907 (13)	2.200 (13)	2.9348 (11)	137.6 (10)
N2—H1N2···O1Wⁱⁱ	0.887 (13)	2.262 (13)	3.1242 (12)	164.1 (11)
O1W—H1O1···Cl1	0.833 (19)	2.400 (19)	3.2329 (14)	178.6 (17)
O1W—H2O1···Cl1ⁱⁱⁱ	0.820 (18)	2.335 (18)	3.1479 (10)	171.1 (15)
O2W—H1O2···O1W^iv	0.84 (2)	2.06 (2)	2.9021 (15)	178.1 (18)

Symmetry codes: (i) −x+1/2, −y+1/2, −z+1; (ii) −x+1/2, y−1/2, −z+1/2; (iii) x, −y+1, z−1/2; (iv) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The experiment at the PLS-II 2D-SMC beamline was supported in part by MEST and POSTECH.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,14-Di­ethyl-2,13-di­aza-6,17-diazonia­tri­cyclo­[16.4.0.07,12]do­cosane dichloride tetra­hydrate from synchrotron radiation

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,14-Diethyl-2,13-diaza-6,17-diazoniatricyclo[16.4.0.0^7,12]docosane dichloride tetrahydrate from synchrotron radiation