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The structures of di­aqua(1,7-dioxa-4-thia-10-aza­cyclo­do­decane)­nickel dinitrate, [Ni(C8H17NO2S)(H2O)2](NO3)2, (I), bis­(nitrato-O,O')(1,4,7-trioxa-10-aza­cyclo­do­decane)­mercury, [Hg(NO3)2(C8H17NO3)], (II), and aqua­(nitrato-O)(1-oxa-4,7,10-tri­aza­cyclo­do­decane)copper nitrate, [Cu(NO3)(C8H19N3O)(H2O)]NO3, (III), reveal each macrocycle binding in a tetradentate manner. The conformations of the ligands in (I) and (III) are the same and distinct from that identified for (II). These differences are in agreement with molecular-mechanics predictions of ligand conformation as a function of metal-ion size.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003942/fg1589sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003942/fg1589Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003942/fg1589IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003942/fg1589IIIsup4.hkl
Contains datablock III

Computing details top

For all compounds, data collection: CAD4 Manual (Enraf-Nonius, 1988); cell refinement: SET4 in CAD4 Manual (Enraf-Nonius, 1988); data reduction: Xtal3.2 (Hall et al., 1992); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.

(I) diaqua(1,7-dioxa-4-thia-10-azacyclododecane)nickel(II) nitrate top
Crystal data top
[Ni(C8H17NO2S)(H2O)2](NO3)2Dx = 1.671 Mg m3
Mr = 410.05Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P65Cell parameters from 25 reflections
a = 8.7242 (3) Åθ = 10–14°
c = 37.102 (3) ŵ = 1.37 mm1
V = 2445.6 (2) Å3T = 295 K
Z = 6Prism, blue
F(000) = 12840.40 × 0.40 × 0.40 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
1208 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 25.0°, θmin = 2.7°
ω–2θ scansh = 108
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.529, Tmax = 0.578l = 044
4648 measured reflections3 standard reflections every 120 min
1459 independent reflections intensity decay: <5%
Refinement top
Refinement on F2Hydrogen site location: constr
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.032Calculated w = 1/[σ2(Fo2) + (0.0398P)2 + 0.4947P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.078(Δ/σ)max < 0.001
S = 1.06Δρmax = 0.28 e Å3
1459 reflectionsΔρmin = 0.26 e Å3
209 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0010 (4)
Primary atom site location: PattersonAbsolute structure: Flack (1983)
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (2)
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
xyzUiso*/Ueq
Ni10.75006 (9)0.41459 (9)0.000389 (18)0.0430 (2)
S10.9037 (2)0.3596 (2)0.04843 (5)0.0582 (4)
N10.5691 (6)0.3561 (7)0.04125 (13)0.0499 (12)
H10.56470.45490.04740.060*
O10.5335 (5)0.1894 (6)0.02155 (11)0.0520 (10)
O20.8233 (6)0.2631 (6)0.03031 (11)0.0550 (11)
O30.6839 (6)0.5672 (6)0.03044 (14)0.0691 (13)
H310.67410.65040.01510.083*
H320.77400.62990.04820.083*
O40.9611 (6)0.6302 (7)0.02131 (16)0.0859 (17)
H410.92230.70460.03230.103*
H421.04470.69450.00260.103*
C10.7108 (9)0.1682 (10)0.06758 (19)0.0665 (19)
H1A0.72530.16700.09350.080*
H1B0.70240.06100.05780.080*
C20.5431 (10)0.1692 (12)0.0598 (2)0.072 (2)
H2A0.54210.26580.07250.086*
H2B0.44180.05890.06760.086*
C30.3771 (9)0.1881 (10)0.00996 (18)0.067 (2)
H3A0.27360.07560.01590.080*
H3B0.36650.28180.02170.080*
C40.3920 (8)0.2148 (10)0.0299 (2)0.069 (2)
H4A0.30440.24490.03790.083*
H4B0.36600.10480.04160.083*
C50.6395 (10)0.3015 (11)0.07165 (18)0.0654 (19)
H5A0.54860.24370.08990.078*
H5B0.73830.40500.08250.078*
C60.6987 (10)0.1761 (10)0.05882 (19)0.0652 (18)
H6A0.75460.14840.07840.078*
H6B0.59850.06680.05030.078*
C70.8742 (10)0.1530 (9)0.01084 (19)0.0678 (19)
H7A0.76970.04890.00170.081*
H7B0.93640.11430.02680.081*
C80.9914 (9)0.2567 (10)0.01959 (19)0.0635 (18)
H8A1.01480.17820.03410.076*
H8B1.10360.34780.00990.076*
N20.8882 (8)0.8688 (9)0.08374 (19)0.0651 (15)
O50.8887 (7)0.9633 (9)0.10823 (18)0.102 (2)
O61.0205 (10)0.9026 (10)0.0676 (2)0.118 (3)
O70.7530 (12)0.7405 (11)0.0759 (3)0.156 (4)
N30.4020 (7)0.7017 (7)0.0053 (2)0.0670 (18)
O80.3719 (11)0.5637 (10)0.0178 (2)0.126 (2)
O90.5279 (9)0.7712 (9)0.01627 (17)0.106 (2)
O100.3128 (9)0.7616 (9)0.0127 (4)0.155 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0387 (4)0.0429 (4)0.0466 (4)0.0197 (3)0.0031 (3)0.0004 (3)
S10.0593 (9)0.0608 (10)0.0587 (10)0.0332 (8)0.0139 (8)0.0024 (8)
N10.047 (3)0.054 (3)0.049 (3)0.026 (2)0.004 (2)0.001 (2)
O10.046 (2)0.059 (2)0.050 (2)0.025 (2)0.0055 (19)0.010 (2)
O20.060 (3)0.066 (3)0.049 (2)0.038 (2)0.003 (2)0.000 (2)
O30.075 (3)0.066 (3)0.079 (3)0.045 (3)0.021 (3)0.022 (2)
O40.052 (3)0.064 (3)0.119 (4)0.011 (2)0.015 (3)0.037 (3)
C10.078 (5)0.082 (5)0.050 (4)0.048 (4)0.004 (3)0.014 (4)
C20.070 (5)0.080 (5)0.069 (5)0.040 (4)0.019 (4)0.023 (4)
C30.042 (3)0.067 (4)0.086 (6)0.024 (3)0.011 (3)0.009 (4)
C40.041 (3)0.081 (5)0.077 (5)0.024 (4)0.012 (3)0.008 (4)
C50.065 (4)0.082 (5)0.047 (4)0.035 (4)0.005 (3)0.003 (3)
C60.068 (4)0.079 (5)0.053 (4)0.040 (4)0.007 (3)0.018 (4)
C70.070 (4)0.077 (5)0.076 (5)0.051 (4)0.014 (4)0.003 (4)
C80.056 (4)0.071 (4)0.074 (5)0.040 (3)0.000 (3)0.008 (4)
N20.060 (4)0.059 (4)0.082 (4)0.035 (3)0.010 (3)0.000 (3)
O50.075 (4)0.099 (4)0.125 (6)0.040 (4)0.004 (3)0.051 (4)
O60.100 (5)0.109 (5)0.160 (7)0.063 (4)0.061 (5)0.016 (5)
O70.122 (6)0.101 (5)0.176 (8)0.005 (5)0.031 (6)0.062 (5)
N30.053 (3)0.047 (3)0.094 (5)0.020 (3)0.005 (3)0.012 (3)
O80.131 (6)0.093 (5)0.151 (6)0.055 (5)0.003 (5)0.022 (5)
O90.097 (5)0.103 (5)0.099 (5)0.036 (4)0.031 (4)0.014 (4)
O100.077 (4)0.093 (5)0.301 (13)0.048 (4)0.037 (6)0.031 (6)
Geometric parameters (Å, º) top
Ni1—O42.028 (5)O2—C61.432 (8)
Ni1—O32.029 (5)O2—C71.438 (8)
Ni1—O22.073 (4)C1—C21.495 (9)
Ni1—N12.082 (5)C3—C41.494 (10)
Ni1—O12.082 (4)C5—C61.502 (11)
Ni1—S12.4185 (17)C7—C81.488 (10)
S1—C81.795 (7)N2—O71.187 (10)
S1—C11.821 (7)N2—O61.200 (8)
N1—C51.473 (9)N2—O51.225 (8)
N1—C41.476 (8)N3—O101.166 (10)
O1—C31.426 (7)N3—O81.190 (9)
O1—C21.438 (8)N3—O91.245 (9)
O4—Ni1—O391.9 (2)C3—O1—C2114.3 (5)
O4—Ni1—O287.0 (2)C3—O1—Ni1107.9 (4)
O3—Ni1—O2178.8 (2)C2—O1—Ni1114.0 (4)
O4—Ni1—N199.1 (2)C6—O2—C7115.0 (5)
O3—Ni1—N198.0 (2)C6—O2—Ni1110.4 (4)
O2—Ni1—N182.75 (18)C7—O2—Ni1116.5 (4)
O4—Ni1—O1178.5 (2)C2—C1—S1112.2 (5)
O3—Ni1—O189.45 (19)O1—C2—C1107.9 (6)
O2—Ni1—O191.66 (17)O1—C3—C4106.8 (5)
N1—Ni1—O180.19 (17)N1—C4—C3112.7 (5)
O4—Ni1—S198.07 (15)N1—C5—C6110.1 (6)
O3—Ni1—S195.33 (15)O2—C6—C5107.1 (6)
O2—Ni1—S184.27 (12)O2—C7—C8108.8 (6)
N1—Ni1—S1157.83 (14)C7—C8—S1114.9 (5)
O1—Ni1—S182.31 (12)O7—N2—O6119.4 (8)
C8—S1—C1101.7 (4)O7—N2—O5118.9 (7)
C8—S1—Ni194.4 (2)O6—N2—O5121.7 (8)
C1—S1—Ni196.9 (2)O10—N3—O8120.2 (9)
C5—N1—C4112.3 (6)O10—N3—O9123.9 (8)
C5—N1—Ni1105.1 (4)O8—N3—O9115.9 (8)
C4—N1—Ni1110.0 (4)
O4—Ni1—S1—C878.3 (3)O4—Ni1—O2—C6109.6 (4)
O3—Ni1—S1—C8171.0 (3)O3—Ni1—O2—C6137 (9)
O2—Ni1—S1—C87.8 (3)N1—Ni1—O2—C610.0 (4)
N1—Ni1—S1—C862.2 (4)O1—Ni1—O2—C669.9 (4)
O1—Ni1—S1—C8100.2 (3)S1—Ni1—O2—C6152.0 (4)
O4—Ni1—S1—C1179.3 (3)O4—Ni1—O2—C7116.8 (5)
O3—Ni1—S1—C186.5 (3)O3—Ni1—O2—C789 (9)
O2—Ni1—S1—C194.6 (3)N1—Ni1—O2—C7143.7 (5)
N1—Ni1—S1—C140.3 (5)O1—Ni1—O2—C763.8 (4)
O1—Ni1—S1—C12.2 (3)S1—Ni1—O2—C718.3 (4)
O4—Ni1—N1—C566.7 (5)C8—S1—C1—C2121.5 (6)
O3—Ni1—N1—C5160.0 (4)Ni1—S1—C1—C225.5 (6)
O2—Ni1—N1—C519.0 (4)C3—O1—C2—C1178.5 (6)
O1—Ni1—N1—C5112.0 (4)Ni1—O1—C2—C156.8 (7)
S1—Ni1—N1—C573.6 (6)S1—C1—C2—O153.0 (8)
O4—Ni1—N1—C4172.2 (4)C2—O1—C3—C4178.7 (6)
O3—Ni1—N1—C479.0 (5)Ni1—O1—C3—C450.7 (6)
O2—Ni1—N1—C4102.0 (4)C5—N1—C4—C3132.8 (6)
O1—Ni1—N1—C49.1 (4)Ni1—N1—C4—C316.2 (7)
S1—Ni1—N1—C447.4 (6)O1—C3—C4—N144.5 (8)
O4—Ni1—O1—C395 (7)C4—N1—C5—C674.6 (7)
O3—Ni1—O1—C364.4 (4)Ni1—N1—C5—C645.0 (7)
O2—Ni1—O1—C3116.2 (4)C7—O2—C6—C5170.8 (5)
N1—Ni1—O1—C333.8 (4)Ni1—O2—C6—C536.4 (7)
S1—Ni1—O1—C3159.8 (4)N1—C5—C6—O255.4 (8)
O4—Ni1—O1—C2137 (7)C6—O2—C7—C8175.4 (5)
O3—Ni1—O1—C263.7 (4)Ni1—O2—C7—C843.8 (6)
O2—Ni1—O1—C2115.8 (4)O2—C7—C8—S152.6 (7)
N1—Ni1—O1—C2161.9 (4)C1—S1—C8—C764.2 (6)
S1—Ni1—O1—C231.8 (4)Ni1—S1—C8—C733.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O70.912.443.177 (9)139
N1—H1···O80.912.563.180 (9)126
O3—H31···O90.962.022.779 (8)134
O3—H31···O80.962.653.244 (10)121
O3—H32···O5i0.962.002.734 (7)132
O3—H32···O7i0.962.403.347 (9)171
O3—H32···N2i0.962.553.465 (8)160
O4—H41···O60.961.992.763 (9)136
O4—H41···O70.962.323.174 (10)149
O4—H41···N20.962.493.380 (8)154
O4—H42···O10ii0.962.142.704 (8)116
Symmetry codes: (i) xy+1, x, z1/6; (ii) x+1, y, z.
(II) bis(nitrato)(1,4,7-trioxa-10-azacyclododecane)mercury(II) top
Crystal data top
[Hg(C8H17NO3)(NO3)2]F(000) = 952
Mr = 499.84Dx = 2.381 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.245 (3) ÅCell parameters from 25 reflections
b = 11.927 (2) Åθ = 10–14°
c = 14.272 (5) ŵ = 11.09 mm1
β = 96.60 (2)°T = 275 K
V = 1394.2 (7) Å3Prism, colourless
Z = 40.30 × 0.20 × 0.20 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
2082 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω–2θ scansh = 09
Absorption correction: ψ scan
(North et al., 1968)
k = 014
Tmin = 0.055, Tmax = 0.109l = 1616
2623 measured reflections3 standard reflections every 120 min
2444 independent reflections intensity decay: <5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.087Calculated w = 1/[σ2(Fo2) + (0.0622P)2 + 1.3329P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
2444 reflectionsΔρmax = 1.46 e Å3
191 parametersΔρmin = 3.30 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: PattersonExtinction coefficient: 0.0018 (3)
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
xyzUiso*/Ueq
Hg10.07460 (3)0.140753 (19)0.310704 (17)0.03087 (15)
N10.1946 (7)0.2309 (5)0.4327 (4)0.0360 (13)
H10.20460.18100.48130.043*
O10.0481 (6)0.3365 (4)0.3058 (3)0.0365 (11)
O20.1265 (6)0.2609 (4)0.1614 (3)0.0402 (11)
O30.3852 (6)0.1594 (4)0.2794 (4)0.0408 (12)
C10.0879 (9)0.3214 (7)0.4604 (5)0.0415 (17)
H1A0.14540.36340.51210.050*
H1B0.00840.28860.48250.050*
C20.0362 (10)0.4001 (6)0.3802 (5)0.0423 (17)
H2A0.03470.45800.40060.051*
H2B0.13110.43590.35900.051*
C30.0593 (9)0.3885 (7)0.2161 (6)0.0436 (18)
H3A0.08370.46750.22300.052*
H3B0.14900.35520.17560.052*
C40.0939 (11)0.3775 (6)0.1700 (6)0.0448 (19)
H4A0.08020.41250.10830.054*
H4B0.18390.41380.20800.054*
C50.2792 (10)0.2355 (7)0.1308 (6)0.0487 (19)
H5A0.30110.28850.08220.058*
H5B0.27430.16120.10300.058*
C60.4172 (9)0.2394 (7)0.2095 (6)0.048 (2)
H6A0.51950.22190.18540.058*
H6B0.42560.31390.23690.058*
C70.4575 (9)0.1861 (7)0.3726 (6)0.050 (2)
H7A0.56620.21560.36910.060*
H7B0.46840.11780.40970.060*
C80.3621 (8)0.2691 (6)0.4215 (6)0.0415 (17)
H8A0.41950.28450.48340.050*
H8B0.35560.33870.38610.050*
N20.0985 (7)0.0310 (5)0.1530 (4)0.0385 (13)
O40.0454 (6)0.0177 (4)0.1985 (4)0.0425 (12)
O50.1850 (7)0.1050 (5)0.1810 (4)0.0574 (15)
O60.1402 (8)0.0291 (6)0.0863 (4)0.0672 (18)
N30.1663 (6)0.0164 (5)0.4295 (4)0.0332 (13)
O70.2714 (6)0.0165 (4)0.4780 (4)0.0458 (13)
O80.1597 (6)0.1178 (4)0.4103 (4)0.0463 (13)
O90.0676 (7)0.0483 (5)0.4004 (4)0.0545 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.0312 (2)0.0282 (2)0.0330 (2)0.00259 (9)0.00311 (11)0.00102 (10)
N10.043 (3)0.040 (3)0.024 (3)0.008 (3)0.002 (2)0.009 (2)
O10.039 (3)0.031 (2)0.038 (3)0.000 (2)0.001 (2)0.004 (2)
O20.050 (3)0.037 (3)0.036 (3)0.005 (2)0.010 (2)0.003 (2)
O30.032 (3)0.033 (3)0.058 (3)0.005 (2)0.008 (2)0.005 (2)
C10.046 (4)0.045 (4)0.033 (4)0.006 (4)0.008 (3)0.011 (3)
C20.052 (5)0.029 (4)0.045 (4)0.004 (3)0.001 (3)0.012 (3)
C30.047 (4)0.038 (4)0.043 (4)0.009 (3)0.007 (3)0.008 (3)
C40.065 (5)0.032 (4)0.037 (4)0.006 (3)0.005 (4)0.010 (3)
C50.053 (5)0.047 (4)0.049 (4)0.004 (4)0.022 (4)0.003 (4)
C60.042 (4)0.044 (4)0.062 (5)0.003 (3)0.024 (4)0.014 (4)
C70.029 (4)0.052 (5)0.066 (5)0.007 (3)0.003 (3)0.014 (4)
C80.029 (4)0.039 (4)0.054 (4)0.001 (3)0.005 (3)0.004 (3)
N20.038 (3)0.038 (3)0.039 (3)0.000 (3)0.001 (3)0.002 (3)
O40.044 (3)0.035 (3)0.046 (3)0.004 (2)0.007 (2)0.002 (2)
O50.047 (3)0.057 (3)0.067 (4)0.013 (3)0.003 (3)0.011 (3)
O60.060 (4)0.075 (4)0.062 (4)0.003 (3)0.010 (3)0.035 (3)
N30.026 (3)0.041 (3)0.030 (3)0.002 (2)0.007 (2)0.001 (3)
O70.044 (3)0.046 (3)0.047 (3)0.009 (2)0.007 (2)0.015 (2)
O80.040 (3)0.040 (3)0.059 (3)0.001 (2)0.006 (3)0.018 (3)
O90.047 (3)0.059 (4)0.054 (3)0.017 (3)0.008 (3)0.017 (3)
Geometric parameters (Å, º) top
Hg1—O42.166 (5)O2—C41.424 (8)
Hg1—N12.184 (5)O3—C61.427 (9)
Hg1—O82.541 (5)O3—C71.429 (10)
Hg1—O12.543 (5)C1—C21.504 (11)
Hg1—O22.644 (5)C3—C41.495 (11)
Hg1—O32.659 (5)C5—C61.505 (11)
Hg1—O52.698 (6)C7—C81.488 (11)
Hg1—O92.906 (6)N2—O61.208 (8)
N1—C11.474 (9)N2—O51.231 (8)
N1—C81.480 (8)N2—O41.295 (7)
O1—C31.415 (9)N3—O91.228 (7)
O1—C21.420 (8)N3—O71.234 (7)
O2—C51.413 (9)N3—O81.243 (7)
O4—Hg1—N1157.7 (2)C1—N1—Hg1110.1 (4)
O4—Hg1—O8108.29 (19)C8—N1—Hg1114.1 (4)
N1—Hg1—O884.87 (19)C3—O1—C2114.7 (6)
O4—Hg1—O1126.29 (17)C3—O1—Hg1114.3 (4)
N1—Hg1—O173.28 (18)C2—O1—Hg1108.1 (4)
O8—Hg1—O177.79 (16)C5—O2—C4114.9 (6)
O4—Hg1—O277.63 (18)C5—O2—Hg1111.4 (4)
N1—Hg1—O2105.99 (18)C4—O2—Hg1114.2 (4)
O8—Hg1—O2135.48 (16)C6—O3—C7114.2 (6)
O1—Hg1—O265.19 (15)C6—O3—Hg1115.6 (4)
O4—Hg1—O387.69 (18)C7—O3—Hg199.7 (4)
N1—Hg1—O374.71 (19)N1—C1—C2112.3 (6)
O8—Hg1—O3155.73 (18)O1—C2—C1107.9 (6)
O1—Hg1—O3107.86 (15)O1—C3—C4112.9 (6)
O2—Hg1—O364.61 (16)O2—C4—C3107.6 (6)
O4—Hg1—O551.21 (18)O2—C5—C6112.7 (6)
N1—Hg1—O5151.11 (19)O3—C6—C5108.5 (6)
O8—Hg1—O576.85 (19)O3—C7—C8113.5 (6)
O1—Hg1—O581.04 (17)N1—C8—C7113.3 (6)
O2—Hg1—O573.85 (18)O6—N2—O5123.9 (7)
O3—Hg1—O5126.98 (18)O6—N2—O4118.9 (6)
O4—Hg1—O977.50 (17)O5—N2—O4117.1 (6)
N1—Hg1—O9101.51 (17)N2—O4—Hg1107.8 (4)
O8—Hg1—O945.49 (16)N2—O5—Hg183.9 (4)
O1—Hg1—O9123.06 (15)O9—N3—O7121.7 (6)
O2—Hg1—O9152.46 (15)O9—N3—O8119.3 (6)
O3—Hg1—O9125.73 (14)O7—N3—O8118.9 (6)
O5—Hg1—O981.42 (18)N3—O8—Hg1106.5 (4)
C1—N1—C8113.3 (6)N3—O9—Hg188.7 (4)
O4—Hg1—N1—C1178.8 (5)C8—N1—C1—C273.7 (7)
O8—Hg1—N1—C153.6 (4)Hg1—N1—C1—C255.4 (7)
O1—Hg1—N1—C125.2 (4)C3—O1—C2—C1160.8 (6)
O2—Hg1—N1—C182.4 (4)Hg1—O1—C2—C132.0 (7)
O3—Hg1—N1—C1139.6 (5)N1—C1—C2—O159.1 (8)
O5—Hg1—N1—C13.1 (7)C2—O1—C3—C479.6 (8)
O9—Hg1—N1—C196.1 (4)Hg1—O1—C3—C446.1 (8)
O4—Hg1—N1—C850.0 (7)C5—O2—C4—C3171.8 (6)
O8—Hg1—N1—C8177.7 (5)Hg1—O2—C4—C341.3 (7)
O1—Hg1—N1—C8103.5 (5)O1—C3—C4—O258.4 (9)
O2—Hg1—N1—C846.4 (5)C4—O2—C5—C681.5 (8)
O3—Hg1—N1—C810.9 (4)Hg1—O2—C5—C650.3 (7)
O5—Hg1—N1—C8131.8 (5)C7—O3—C6—C5152.9 (6)
O9—Hg1—N1—C8135.1 (4)Hg1—O3—C6—C538.0 (7)
O4—Hg1—O1—C334.5 (5)O2—C5—C6—O360.0 (9)
N1—Hg1—O1—C3133.4 (5)C6—O3—C7—C881.0 (8)
O8—Hg1—O1—C3138.3 (5)Hg1—O3—C7—C842.9 (7)
O2—Hg1—O1—C316.3 (4)C1—N1—C8—C7166.5 (6)
O3—Hg1—O1—C366.1 (5)Hg1—N1—C8—C739.4 (7)
O5—Hg1—O1—C359.9 (5)O3—C7—C8—N160.0 (9)
O9—Hg1—O1—C3133.5 (4)O6—N2—O4—Hg1179.4 (6)
O4—Hg1—O1—C2163.5 (4)O5—N2—O4—Hg10.7 (7)
N1—Hg1—O1—C24.4 (4)N1—Hg1—O4—N2179.2 (5)
O8—Hg1—O1—C292.7 (4)O8—Hg1—O4—N255.4 (4)
O2—Hg1—O1—C2112.7 (5)O1—Hg1—O4—N232.7 (5)
O3—Hg1—O1—C262.9 (5)O2—Hg1—O4—N278.8 (4)
O5—Hg1—O1—C2171.0 (5)O3—Hg1—O4—N2143.3 (4)
O9—Hg1—O1—C297.4 (4)O5—Hg1—O4—N20.3 (4)
O4—Hg1—O2—C572.8 (5)O9—Hg1—O4—N289.3 (4)
N1—Hg1—O2—C584.5 (5)O6—N2—O5—Hg1179.6 (7)
O8—Hg1—O2—C5176.4 (4)O4—N2—O5—Hg10.5 (5)
O1—Hg1—O2—C5146.9 (5)O4—Hg1—O5—N20.4 (4)
O3—Hg1—O2—C520.5 (4)N1—Hg1—O5—N2179.5 (4)
O5—Hg1—O2—C5125.6 (5)O8—Hg1—O5—N2127.3 (4)
O9—Hg1—O2—C598.7 (5)O1—Hg1—O5—N2153.2 (4)
O4—Hg1—O2—C4155.0 (5)O2—Hg1—O5—N286.6 (4)
N1—Hg1—O2—C447.7 (5)O3—Hg1—O5—N247.6 (5)
O8—Hg1—O2—C451.4 (6)O9—Hg1—O5—N281.2 (4)
O1—Hg1—O2—C414.8 (5)O9—N3—O8—Hg10.4 (7)
O3—Hg1—O2—C4111.6 (5)O7—N3—O8—Hg1179.9 (4)
O5—Hg1—O2—C4102.2 (5)O4—Hg1—O8—N349.6 (4)
O9—Hg1—O2—C4129.2 (5)N1—Hg1—O8—N3111.9 (4)
O4—Hg1—O3—C687.9 (5)O1—Hg1—O8—N3174.1 (4)
N1—Hg1—O3—C6105.9 (5)O2—Hg1—O8—N3140.5 (4)
O8—Hg1—O3—C6139.6 (5)O3—Hg1—O8—N379.4 (6)
O1—Hg1—O3—C639.6 (5)O5—Hg1—O8—N390.6 (4)
O2—Hg1—O3—C610.5 (5)O9—Hg1—O8—N30.2 (3)
O5—Hg1—O3—C652.6 (5)O7—N3—O9—Hg1179.8 (5)
O9—Hg1—O3—C6160.7 (5)O8—N3—O9—Hg10.4 (6)
O4—Hg1—O3—C7149.1 (4)O4—Hg1—O9—N3131.7 (4)
N1—Hg1—O3—C717.0 (4)N1—Hg1—O9—N371.1 (4)
O8—Hg1—O3—C716.7 (6)O8—Hg1—O9—N30.2 (3)
O1—Hg1—O3—C783.3 (4)O1—Hg1—O9—N36.4 (4)
O2—Hg1—O3—C7133.5 (4)O2—Hg1—O9—N3105.9 (4)
O5—Hg1—O3—C7175.5 (4)O3—Hg1—O9—N3150.4 (3)
O9—Hg1—O3—C776.3 (4)O5—Hg1—O9—N379.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O7i0.912.102.895 (8)145
Symmetry code: (i) x, y, z+1.
(III) aqua(1,7-dioxa-4-thia-10-azacyclododecane)nitratocopper(II) nitrate top
Crystal data top
[Cu(NO3)(C8H19N3O)(H2O)](NO3)Z = 2
Mr = 378.84F(000) = 394
Triclinic, P1Dx = 1.707 Mg m3
a = 8.6167 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.3975 (8) ÅCell parameters from 25 reflections
c = 10.118 (1) Åθ = 10–14°
α = 95.627 (8)°µ = 1.53 mm1
β = 112.107 (9)°T = 295 K
γ = 99.509 (9)°Prism, blue
V = 737.05 (12) Å30.60 × 0.60 × 0.30 mm
Data collection top
Enraf-Nonius CAD4
diffractometer
2392 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω–2θ scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.401, Tmax = 0.632l = 1211
2774 measured reflections3 standard reflections every 120 min
2586 independent reflections intensity decay: <5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.068Calculated w = 1/[σ2(Fo2) + (0.0343P)2 + 0.4836P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
2586 reflectionsΔρmax = 0.36 e Å3
200 parametersΔρmin = 0.27 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: PattersonExtinction coefficient: 0.096 (3)
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
xyzUiso*/Ueq
Cu10.21252 (3)0.31381 (3)0.28989 (3)0.02718 (12)
N10.4259 (2)0.3414 (2)0.2459 (2)0.0323 (4)
H10.48520.43610.27900.039*
N20.2809 (2)0.13935 (19)0.3690 (2)0.0324 (4)
H20.32920.16330.46740.039*
N30.0304 (2)0.2185 (2)0.2627 (2)0.0358 (4)
H30.07340.28460.30280.043*
O10.1719 (2)0.51182 (16)0.26897 (18)0.0363 (4)
O20.0888 (2)0.22036 (17)0.04050 (17)0.0363 (4)
H210.11580.54110.30730.044*
H220.24440.57200.28250.044*
C10.2013 (3)0.3174 (3)0.0028 (3)0.0417 (6)
H1A0.18900.41750.01440.050*
H1B0.17480.28920.10510.050*
C20.3804 (3)0.3044 (3)0.0871 (3)0.0414 (6)
H2A0.39160.20500.06420.050*
H2B0.46090.36950.06210.050*
C30.5307 (3)0.2438 (3)0.3283 (3)0.0401 (5)
H3A0.59480.29120.42860.048*
H3B0.61180.22390.28740.048*
C40.4125 (3)0.1017 (3)0.3205 (3)0.0409 (5)
H4A0.35850.04810.22190.049*
H4B0.47690.04080.38230.049*
C50.1237 (3)0.0239 (2)0.3266 (3)0.0409 (5)
H5A0.14560.05040.38730.049*
H5B0.08640.02250.22650.049*
C60.0126 (3)0.0955 (3)0.3451 (3)0.0428 (6)
H6A0.12100.02460.30950.051*
H6B0.01950.13220.44690.051*
C70.1451 (3)0.1706 (3)0.1063 (3)0.0458 (6)
H7A0.25830.18770.09030.055*
H7B0.15660.06620.07950.055*
C80.0768 (3)0.2509 (3)0.0112 (3)0.0429 (6)
H8A0.15190.21680.09010.051*
H8B0.06770.35540.03420.051*
N40.1509 (2)0.4333 (2)0.6302 (2)0.0361 (4)
O30.2037 (2)0.5294 (2)0.73981 (19)0.0467 (4)
O40.0026 (2)0.3634 (2)0.5789 (2)0.0533 (5)
O50.2479 (2)0.4077 (2)0.56979 (19)0.0444 (4)
N50.4988 (2)0.2483 (2)0.7541 (2)0.0384 (5)
O60.5639 (2)0.25468 (19)0.66193 (18)0.0443 (4)
O70.3773 (3)0.1476 (2)0.7311 (3)0.0823 (8)
O80.5587 (3)0.3456 (3)0.8614 (2)0.0633 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.02852 (17)0.02262 (16)0.03316 (17)0.00233 (10)0.01675 (11)0.00476 (10)
N10.0321 (9)0.0310 (9)0.0381 (10)0.0037 (8)0.0198 (8)0.0071 (8)
N20.0409 (10)0.0270 (9)0.0319 (9)0.0043 (8)0.0187 (8)0.0056 (7)
N30.0340 (10)0.0297 (9)0.0456 (11)0.0013 (8)0.0223 (9)0.0021 (8)
O10.0398 (9)0.0259 (8)0.0523 (10)0.0050 (6)0.0295 (8)0.0060 (7)
O20.0379 (8)0.0367 (8)0.0354 (8)0.0090 (7)0.0150 (7)0.0076 (7)
C10.0535 (15)0.0449 (14)0.0315 (12)0.0096 (11)0.0214 (11)0.0125 (10)
C20.0482 (14)0.0482 (14)0.0404 (13)0.0101 (11)0.0308 (11)0.0119 (11)
C30.0328 (12)0.0470 (14)0.0459 (13)0.0119 (10)0.0194 (10)0.0123 (11)
C40.0471 (14)0.0360 (12)0.0492 (14)0.0181 (11)0.0245 (11)0.0137 (10)
C50.0526 (14)0.0240 (11)0.0495 (14)0.0007 (10)0.0272 (12)0.0077 (10)
C60.0496 (14)0.0318 (12)0.0525 (14)0.0058 (10)0.0332 (12)0.0042 (10)
C70.0299 (12)0.0427 (14)0.0544 (15)0.0005 (10)0.0121 (11)0.0049 (11)
C80.0371 (12)0.0422 (13)0.0395 (13)0.0104 (10)0.0056 (10)0.0006 (10)
N40.0359 (10)0.0348 (10)0.0412 (11)0.0119 (8)0.0174 (9)0.0074 (8)
O30.0497 (10)0.0459 (10)0.0427 (10)0.0072 (8)0.0206 (8)0.0034 (8)
O40.0367 (9)0.0516 (11)0.0677 (12)0.0017 (8)0.0236 (9)0.0052 (9)
O50.0399 (9)0.0496 (10)0.0497 (10)0.0144 (8)0.0242 (8)0.0014 (8)
N50.0342 (10)0.0364 (11)0.0494 (12)0.0079 (8)0.0205 (9)0.0129 (9)
O60.0470 (10)0.0474 (10)0.0399 (9)0.0017 (8)0.0236 (8)0.0034 (7)
O70.0667 (14)0.0498 (12)0.144 (2)0.0096 (11)0.0681 (16)0.0114 (13)
O80.0663 (13)0.0763 (14)0.0448 (11)0.0028 (11)0.0289 (10)0.0063 (10)
Geometric parameters (Å, º) top
Cu1—O11.9663 (15)O2—C81.428 (3)
Cu1—N21.9742 (18)O2—C11.438 (3)
Cu1—N12.0312 (18)C1—C21.501 (4)
Cu1—N32.0393 (18)C3—C41.515 (3)
Cu1—O22.3465 (16)C5—C61.506 (4)
Cu1—O52.7682 (17)C7—C81.504 (4)
N1—C31.486 (3)N4—O31.241 (3)
N1—C21.493 (3)N4—O51.247 (2)
N2—C41.472 (3)N4—O41.257 (3)
N2—C51.477 (3)N5—O71.222 (3)
N3—C61.484 (3)N5—O81.228 (3)
N3—C71.490 (3)N5—O61.257 (3)
O1—Cu1—N2163.92 (7)C6—N3—C7113.13 (19)
O1—Cu1—N196.37 (7)C6—N3—Cu1105.76 (14)
N2—Cu1—N186.73 (7)C7—N3—Cu1111.33 (14)
O1—Cu1—N396.54 (7)C8—O2—C1116.32 (19)
N2—Cu1—N386.40 (8)C8—O2—Cu197.41 (13)
N1—Cu1—N3156.15 (8)C1—O2—Cu198.62 (13)
O1—Cu1—O295.29 (6)O2—C1—C2106.39 (19)
N2—Cu1—O2100.79 (7)N1—C2—C1112.69 (19)
N1—Cu1—O279.83 (7)N1—C3—C4108.98 (19)
N3—Cu1—O279.07 (7)N2—C4—C3107.58 (19)
O1—Cu1—O581.64 (6)N2—C5—C6107.65 (18)
N2—Cu1—O583.03 (6)N3—C6—C5108.79 (18)
N1—Cu1—O5118.63 (6)N3—C7—C8111.87 (19)
N3—Cu1—O583.11 (7)O2—C8—C7106.0 (2)
O2—Cu1—O5161.46 (5)O3—N4—O5120.5 (2)
C3—N1—C2111.98 (18)O3—N4—O4119.46 (19)
C3—N1—Cu1105.46 (13)O5—N4—O4120.0 (2)
C2—N1—Cu1111.26 (14)N4—O5—Cu1136.44 (14)
C4—N2—C5115.95 (18)O7—N5—O8123.3 (2)
C4—N2—Cu1108.32 (13)O7—N5—O6118.5 (2)
C5—N2—Cu1107.86 (14)O8—N5—O6118.2 (2)
O1—Cu1—N1—C3150.35 (14)O5—Cu1—O2—C822.0 (2)
N2—Cu1—N1—C313.81 (15)O1—Cu1—O2—C160.69 (14)
N3—Cu1—N1—C387.3 (2)N2—Cu1—O2—C1119.50 (14)
O2—Cu1—N1—C3115.40 (15)N1—Cu1—O2—C134.85 (13)
O5—Cu1—N1—C366.42 (16)N3—Cu1—O2—C1156.35 (14)
O1—Cu1—N1—C288.04 (15)O5—Cu1—O2—C1140.12 (18)
N2—Cu1—N1—C2107.80 (16)C8—O2—C1—C2158.04 (19)
N3—Cu1—N1—C234.4 (3)Cu1—O2—C1—C255.31 (19)
O2—Cu1—N1—C26.22 (14)C3—N1—C2—C1141.5 (2)
O5—Cu1—N1—C2171.96 (14)Cu1—N1—C2—C123.7 (2)
O1—Cu1—N2—C4116.4 (2)O2—C1—C2—N158.0 (3)
N1—Cu1—N2—C414.67 (15)C2—N1—C3—C481.9 (2)
N3—Cu1—N2—C4142.48 (16)Cu1—N1—C3—C439.2 (2)
O2—Cu1—N2—C464.33 (15)C5—N2—C4—C3161.1 (2)
O5—Cu1—N2—C4134.04 (15)Cu1—N2—C4—C339.8 (2)
O1—Cu1—N2—C5117.4 (2)N1—C3—C4—N253.5 (2)
N1—Cu1—N2—C5140.89 (15)C4—N2—C5—C6163.2 (2)
N3—Cu1—N2—C516.26 (14)Cu1—N2—C5—C641.6 (2)
O2—Cu1—N2—C561.89 (15)C7—N3—C6—C583.6 (2)
O5—Cu1—N2—C599.74 (14)Cu1—N3—C6—C538.5 (2)
O1—Cu1—N3—C6151.71 (14)N2—C5—C6—N354.1 (3)
N2—Cu1—N3—C612.42 (14)C6—N3—C7—C8140.1 (2)
N1—Cu1—N3—C685.9 (2)Cu1—N3—C7—C821.2 (2)
O2—Cu1—N3—C6114.14 (14)C1—O2—C8—C7161.99 (19)
O5—Cu1—N3—C670.99 (14)Cu1—O2—C8—C758.53 (18)
O1—Cu1—N3—C785.03 (16)N3—C7—C8—O258.9 (2)
N2—Cu1—N3—C7110.84 (16)O3—N4—O5—Cu1148.60 (17)
N1—Cu1—N3—C737.3 (3)O4—N4—O5—Cu130.2 (3)
O2—Cu1—N3—C79.12 (15)O1—Cu1—O5—N471.5 (2)
O5—Cu1—N3—C7165.75 (16)N2—Cu1—O5—N4113.4 (2)
O1—Cu1—O2—C857.47 (14)N1—Cu1—O5—N4164.2 (2)
N2—Cu1—O2—C8122.34 (14)N3—Cu1—O5—N426.2 (2)
N1—Cu1—O2—C8153.01 (14)O2—Cu1—O5—N410.2 (3)
N3—Cu1—O2—C838.19 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.912.363.153 (3)145
N1—H1···O8i0.912.613.234 (3)127
N2—H2···O60.912.192.994 (3)147
N2—H2···O70.912.563.428 (4)159
N2—H2···N50.912.683.582 (3)174
N3—H3···O3ii0.912.223.000 (3)143
N3—H3···O40.912.623.257 (3)127
O1—H21···O4ii0.792.002.788 (2)172
O1—H21···O3ii0.792.573.162 (2)133
O1—H21···N4ii0.792.643.398 (2)161
O1—H22···O6i0.731.982.709 (2)174
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1.
 

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