1,4,8,11-Tetra-azoniacyclo-tetradecane diaqua-tetra-chloridomanganese(II) dichloride dihydrate.

The title compound, (C(10)H(28)N(4))[MnCl(4)(H(2)O)(2)]Cl(2)·2H(2)O, consists of isolated octa-hedral [MnCl(4)(H(2)O)(2)](2-) anions, tetra-protonated 1,4,8,11-tetra-azoniacyclo-tetradecane cations, chloride anions and water mol-ecules connected by a network of hydrogen bonds. The Mn(II) atom is situated on an inversion centre, and the 1,4,8,11-tetra-azoniacyclo-tetradecane cation is located on a mirror plane.

Related literature

For bond distances and angles in the cyclam mol­ecule, see: Melson (1979 ▶).

Experimental

Crystal data

(C10H28N4)[MnCl4(H2O)2]Cl2·2H2O

M = 544.1

Orthorhombic,

a = 14.8492 (2) Å

b = 19.3511 (3) Å

c = 7.8772 (1) Å

V = 2263.50 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.31 mm−1

T = 292 K

0.36 × 0.22 × 0.16 mm

Data collection

Oxford Diffraction CCD diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005 ▶) T min = 0.721, T max = 0.840

26200 measured reflections

2429 independent reflections

1999 reflections with I > 3σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.059

S = 1.09

2429 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.10 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2005 ▶); data reduction: CrysAlis RED; 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 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031958/bt5316sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031958/bt5316Isup2.hkl

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

(C10H28N4)[MnCl4(H2O)2]Cl2·2H2O	F(000) = 1132
Mr = 544.1	Dx = 1.596 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2n	Cell parameters from 16479 reflections
a = 14.8492 (2) Å	θ = 2.5–26.5°
b = 19.3511 (3) Å	µ = 1.31 mm−1
c = 7.8772 (1) Å	T = 292 K
V = 2263.50 (5) Å3	Prism, colourless
Z = 4	0.36 × 0.22 × 0.16 mm

Oxford Diffraction CCD diffractometer	2429 independent reflections
Radiation source: X-ray tube	1999 reflections with I > 3σ(I)
graphite	Rint = 0.026
Detector resolution: 8.3438 pixels mm-1	θmax = 26.5°, θmin = 2.7°
Rotation method data acquisition using ω scans	h = −18→18
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2005)	k = −24→24
Tmin = 0.721, Tmax = 0.840	l = −9→9
26200 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.018	Hydrogen site location: difference Fourier map
wR(F2) = 0.059	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0016I2]
2429 reflections	(Δ/σ)max = 0.010
133 parameters	Δρmax = 0.14 e Å−3
Primary atom site location: structure-invariant direct methods	Δρmin = −0.10 e Å−3

Experimental. CrysAlis RED, Oxford Diffraction Ltd., Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid.

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.All the H atoms were discrenible in difference Fourier maps and could be refined to reasonable geometry. Despite of it the H atoms bonded to catbon and nitrogen atoms were constrained to ideal positions. The O—H distances were restrained to 0.82 Å with σ 0.01. The isotropic temperature parameters of hydrogen atoms were calculated as 1.2*Ueq of the parent atom.The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details,

	x	y	z	Uiso*/Ueq
Mn1	0	0	0	0.01920 (9)
Cl1	−0.06104 (2)	0.040619 (17)	0.28548 (4)	0.02344 (10)
Cl3	0.03588 (3)	0.25	0.10590 (6)	0.02742 (14)
Cl2	0.14001 (2)	−0.046308 (19)	0.14869 (4)	0.03195 (11)
Cl4	0.27203 (4)	0.25	0.80690 (7)	0.03300 (16)
O1	0.06526 (7)	0.10208 (5)	−0.04773 (13)	0.0246 (3)
O2	0.24961 (7)	0.11049 (6)	−0.02640 (14)	0.0323 (3)
N1	0.25833 (7)	0.12044 (5)	0.33251 (14)	0.0211 (3)
N2	0.04152 (7)	0.12050 (5)	0.59062 (14)	0.0203 (3)
C1	0.15939 (9)	0.11683 (7)	0.36796 (16)	0.0212 (4)
C2	0.14089 (8)	0.11699 (7)	0.55731 (17)	0.0206 (4)
C3	−0.00618 (8)	0.18592 (7)	0.54150 (17)	0.0217 (4)
C4	0.03729 (16)	0.25	0.6165 (3)	0.0314 (6)
C5	0.30646 (9)	0.18591 (6)	0.38037 (17)	0.0228 (4)
C6	0.26338 (16)	0.25	0.3046 (3)	0.0329 (7)
H1m	0.268045	0.111373	0.225895	0.0253*
H1n	0.285152	0.085355	0.379572	0.0253*
H2m	0.031159	0.111526	0.697062	0.0244*
H2n	0.015046	0.085424	0.542836	0.0244*
H1a	0.134992	0.075561	0.318388	0.0254*
H1b	0.129816	0.155584	0.31619	0.0254*
H2a	0.165029	0.07569	0.607205	0.0247*
H2b	0.169981	0.156082	0.608522	0.0247*
H3a	−0.067928	0.183451	0.577083	0.026*
H3n	−0.007609	0.18981	0.420039	0.026*
H4a	0.100476	0.25	0.590704	0.0377*
H4b	0.029252	0.25	0.737419	0.0377*
H5a	0.368181	0.18312	0.344749	0.0273*
H5b	0.308095	0.190111	0.50176	0.0273*
H6a	0.200057	0.25	0.329167	0.0394*
H6b	0.272047	0.25	0.183783	0.0394*
H2o	0.2545 (12)	0.1474 (6)	−0.080 (2)	0.0387*
H2p	0.2810 (10)	0.0859 (8)	−0.085 (2)	0.0387*
H1o	0.1201 (6)	0.1002 (8)	−0.042 (2)	0.0296*
H1p	0.0475 (11)	0.1365 (6)	0.0039 (18)	0.0296*

	U11	U22	U33	U12	U13	U23
Mn1	0.02119 (16)	0.01807 (15)	0.01834 (15)	0.00097 (11)	−0.00088 (10)	0.00132 (11)
Cl1	0.0257 (2)	0.02367 (17)	0.02098 (17)	0.00260 (12)	−0.00054 (12)	−0.00266 (13)
Cl3	0.0298 (3)	0.0235 (2)	0.0290 (3)	0	−0.0005 (2)	0
Cl2	0.0316 (2)	0.0361 (2)	0.02823 (19)	0.01481 (15)	−0.00806 (14)	−0.00686 (15)
Cl4	0.0394 (3)	0.0291 (3)	0.0305 (3)	0	−0.0040 (2)	0
O1	0.0262 (5)	0.0217 (5)	0.0260 (5)	−0.0011 (4)	0.0017 (4)	−0.0027 (4)
O2	0.0351 (6)	0.0327 (6)	0.0290 (6)	0.0005 (5)	0.0060 (4)	0.0008 (5)
N1	0.0225 (6)	0.0184 (5)	0.0224 (6)	0.0031 (4)	0.0018 (4)	−0.0012 (5)
N2	0.0223 (6)	0.0179 (5)	0.0207 (6)	−0.0024 (4)	0.0023 (4)	0.0014 (4)
C1	0.0198 (6)	0.0208 (6)	0.0230 (7)	−0.0017 (5)	−0.0010 (5)	−0.0022 (5)
C2	0.0186 (6)	0.0221 (6)	0.0210 (6)	0.0009 (5)	−0.0010 (5)	0.0026 (5)
C3	0.0191 (7)	0.0200 (7)	0.0259 (7)	0.0011 (5)	−0.0014 (5)	0.0002 (6)
C4	0.0448 (13)	0.0191 (9)	0.0304 (11)	0	−0.0135 (10)	0
C5	0.0185 (7)	0.0214 (7)	0.0285 (7)	−0.0010 (5)	−0.0013 (5)	0.0002 (6)
C6	0.0451 (13)	0.0208 (10)	0.0327 (12)	0	−0.0135 (9)	0

Mn1—Cl1	2.5488 (3)	N2—H2n	0.8700
Mn1—Cl1i	2.5488 (3)	C1—C2	1.5166 (18)
Mn1—Cl2	2.5490 (4)	C1—H1a	0.9600
Mn1—Cl2i	2.5490 (4)	C1—H1b	0.9600
Mn1—O1	2.2322 (10)	C2—H2a	0.9600
Mn1—O1i	2.2322 (10)	C2—H2b	0.9600
O1—H1o	0.817 (9)	C3—C4	1.5176 (18)
O1—H1p	0.824 (13)	C3—H3a	0.9600
O2—H2o	0.833 (13)	C3—H3n	0.9600
O2—H2p	0.812 (15)	C4—H4a	0.960
N1—C1	1.4971 (17)	C4—H4b	0.960
N1—C5	1.5026 (16)	C5—C6	1.5179 (18)
N1—H1m	0.8700	C5—H5a	0.9600
N1—H1n	0.8700	C5—H5b	0.9600
N2—C2	1.5004 (16)	C6—H6a	0.960
N2—C3	1.5013 (17)	C6—H6b	0.960
N2—H2m	0.8700
Cl1—Mn1—Cl1i	180	C2—C1—H1b	109.47
Cl1—Mn1—Cl2	89.601 (11)	H1a—C1—H1b	107.72
Cl1—Mn1—Cl2i	90.399 (11)	N2—C2—C1	110.50 (10)
Cl1—Mn1—O1	91.72 (3)	N2—C2—H2a	109.47
Cl1—Mn1—O1i	88.28 (3)	N2—C2—H2b	109.47
Cl1i—Mn1—Cl2	90.399 (11)	C1—C2—H2a	109.47
Cl1i—Mn1—Cl2i	89.601 (11)	C1—C2—H2b	109.47
Cl1i—Mn1—O1	88.28 (3)	H2a—C2—H2b	108.42
Cl1i—Mn1—O1i	91.72 (3)	N2—C3—C4	112.83 (11)
Cl2—Mn1—Cl2i	180	N2—C3—H3a	109.47
Cl2—Mn1—O1	91.97 (3)	N2—C3—H3n	109.47
Cl2—Mn1—O1i	88.03 (3)	C4—C3—H3a	109.47
Cl2i—Mn1—O1	88.03 (3)	C4—C3—H3n	109.47
Cl2i—Mn1—O1i	91.97 (3)	H3a—C3—H3n	105.89
O1—Mn1—O1i	180	C3—C4—C3ii	109.58 (15)
H1o—O1—H1p	109.3 (16)	C3—C4—H4a	109.47
H2o—O2—H2p	99.4 (15)	C3—C4—H4b	109.47
C1—N1—C5	117.34 (10)	C3ii—C4—H4a	109.47
C1—N1—H1m	109.47	C3ii—C4—H4b	109.47
C1—N1—H1n	109.47	H4a—C4—H4b	109.4
C5—N1—H1m	109.47	N1—C5—C6	112.94 (12)
C5—N1—H1n	109.47	N1—C5—H5a	109.47
H1m—N1—H1n	100.26	N1—C5—H5b	109.47
C2—N2—C3	117.20 (10)	C6—C5—H5a	109.47
C2—N2—H2m	109.47	C6—C5—H5b	109.47
C2—N2—H2n	109.47	H5a—C5—H5b	105.77
C3—N2—H2m	109.47	C5—C6—C5ii	109.58 (16)
C3—N2—H2n	109.47	C5—C6—H6a	109.47
H2m—N2—H2n	100.45	C5—C6—H6b	109.47
N1—C1—C2	111.17 (10)	C5ii—C6—H6a	109.47
N1—C1—H1a	109.47	C5ii—C6—H6b	109.47
N1—C1—H1b	109.47	H6a—C6—H6b	109.4
C2—C1—H1a	109.47

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1M···O2	0.87	2.01	2.8367 (16)	159
N1—H1N···Cl2iii	0.87	2.51	3.2465 (11)	143
N1—H1N···Cl1iv	0.87	2.77	3.2317 (11)	115
O1—H1O···O2	0.816 (9)	1.937 (9)	2.7474 (15)	171.5 (15)
O1—H1P···Cl3	0.824 (13)	2.345 (12)	3.1382 (10)	161.8 (14)
N2—H2M···O1v	0.87	2.08	2.8926 (15)	155
N2—H2N···Cl1	0.87	2.48	3.2383 (11)	146
O2—H2O···Cl4vi	0.833 (13)	2.192 (13)	3.0205 (12)	173.4 (14)
O2—H2P···Cl2vii	0.810 (15)	2.523 (16)	3.2832 (11)	156.8 (14)
C1—H1A···Cl2	0.96	2.71	3.6100 (14)	156
C3—H3N···Cl3	0.96	2.81	3.7016 (14)	155
C5—H5B···Cl4	0.96	2.72	3.6178 (14)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1M⋯O2	0.87	2.01	2.8367 (16)	159
N1—H1N⋯Cl2i	0.87	2.51	3.2465 (11)	143
N1—H1N⋯Cl1ii	0.87	2.77	3.2317 (11)	115
O1—H1O⋯O2	0.82 (1)	1.94 (1)	2.7474 (15)	172 (2)
O1—H1P⋯Cl3	0.82 (1)	2.35 (1)	3.1382 (10)	162 (1)
N2—H2M⋯O1iii	0.87	2.08	2.8926 (15)	155
N2—H2N⋯Cl1	0.87	2.48	3.2383 (11)	146
O2—H2O⋯Cl4iv	0.83 (1)	2.19 (1)	3.0205 (12)	173 (1)
O2—H2P⋯Cl2v	0.81 (2)	2.52 (2)	3.2832 (11)	157 (1)
C1—H1A⋯Cl2	0.96	2.71	3.6100 (14)	156
C3—H3N⋯Cl3	0.96	2.81	3.7016 (14)	155
C5—H5B⋯Cl4	0.96	2.72	3.6178 (14)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .