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
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)2 | Dx = 1.671 Mg m−3 |
Mr = 410.05 | Mo Kα radiation, λ = 0.71073 Å |
Hexagonal, P65 | Cell parameters from 25 reflections |
a = 8.7242 (3) Å | θ = 10–14° |
c = 37.102 (3) Å | µ = 1.37 mm−1 |
V = 2445.6 (2) Å3 | T = 295 K |
Z = 6 | Prism, blue |
F(000) = 1284 | 0.40 × 0.40 × 0.40 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | 1208 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 25.0°, θmin = 2.7° |
ω–2θ scans | h = −10→8 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→10 |
Tmin = 0.529, Tmax = 0.578 | l = 0→44 |
4648 measured reflections | 3 standard reflections every 120 min |
1459 independent reflections | intensity decay: <5% |
Refinement top
Refinement on F2 | Hydrogen site location: constr |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | Calculated w = 1/[σ2(Fo2) + (0.0398P)2 + 0.4947P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.078 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.28 e Å−3 |
1459 reflections | Δρmin = −0.26 e Å−3 |
209 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0010 (4) |
Primary atom site location: Patterson | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute 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 | x | y | z | Uiso*/Ueq | |
Ni1 | 0.75006 (9) | 0.41459 (9) | −0.000389 (18) | 0.0430 (2) | |
S1 | 0.9037 (2) | 0.3596 (2) | −0.04843 (5) | 0.0582 (4) | |
N1 | 0.5691 (6) | 0.3561 (7) | 0.04125 (13) | 0.0499 (12) | |
H1 | 0.5647 | 0.4549 | 0.0474 | 0.060* | |
O1 | 0.5335 (5) | 0.1894 (6) | −0.02155 (11) | 0.0520 (10) | |
O2 | 0.8233 (6) | 0.2631 (6) | 0.03031 (11) | 0.0550 (11) | |
O3 | 0.6839 (6) | 0.5672 (6) | −0.03044 (14) | 0.0691 (13) | |
H31 | 0.6741 | 0.6504 | −0.0151 | 0.083* | |
H32 | 0.7740 | 0.6299 | −0.0482 | 0.083* | |
O4 | 0.9611 (6) | 0.6302 (7) | 0.02131 (16) | 0.0859 (17) | |
H41 | 0.9223 | 0.7046 | 0.0323 | 0.103* | |
H42 | 1.0447 | 0.6945 | 0.0026 | 0.103* | |
C1 | 0.7108 (9) | 0.1682 (10) | −0.06758 (19) | 0.0665 (19) | |
H1A | 0.7253 | 0.1670 | −0.0935 | 0.080* | |
H1B | 0.7024 | 0.0610 | −0.0578 | 0.080* | |
C2 | 0.5431 (10) | 0.1692 (12) | −0.0598 (2) | 0.072 (2) | |
H2A | 0.5421 | 0.2658 | −0.0725 | 0.086* | |
H2B | 0.4418 | 0.0589 | −0.0676 | 0.086* | |
C3 | 0.3771 (9) | 0.1881 (10) | −0.00996 (18) | 0.067 (2) | |
H3A | 0.2736 | 0.0756 | −0.0159 | 0.080* | |
H3B | 0.3665 | 0.2818 | −0.0217 | 0.080* | |
C4 | 0.3920 (8) | 0.2148 (10) | 0.0299 (2) | 0.069 (2) | |
H4A | 0.3044 | 0.2449 | 0.0379 | 0.083* | |
H4B | 0.3660 | 0.1048 | 0.0416 | 0.083* | |
C5 | 0.6395 (10) | 0.3015 (11) | 0.07165 (18) | 0.0654 (19) | |
H5A | 0.5486 | 0.2437 | 0.0899 | 0.078* | |
H5B | 0.7383 | 0.4050 | 0.0825 | 0.078* | |
C6 | 0.6987 (10) | 0.1761 (10) | 0.05882 (19) | 0.0652 (18) | |
H6A | 0.7546 | 0.1484 | 0.0784 | 0.078* | |
H6B | 0.5985 | 0.0668 | 0.0503 | 0.078* | |
C7 | 0.8742 (10) | 0.1530 (9) | 0.01084 (19) | 0.0678 (19) | |
H7A | 0.7697 | 0.0489 | 0.0017 | 0.081* | |
H7B | 0.9364 | 0.1143 | 0.0268 | 0.081* | |
C8 | 0.9914 (9) | 0.2567 (10) | −0.01959 (19) | 0.0635 (18) | |
H8A | 1.0148 | 0.1782 | −0.0341 | 0.076* | |
H8B | 1.1036 | 0.3478 | −0.0099 | 0.076* | |
N2 | 0.8882 (8) | 0.8688 (9) | 0.08374 (19) | 0.0651 (15) | |
O5 | 0.8887 (7) | 0.9633 (9) | 0.10823 (18) | 0.102 (2) | |
O6 | 1.0205 (10) | 0.9026 (10) | 0.0676 (2) | 0.118 (3) | |
O7 | 0.7530 (12) | 0.7405 (11) | 0.0759 (3) | 0.156 (4) | |
N3 | 0.4020 (7) | 0.7017 (7) | 0.0053 (2) | 0.0670 (18) | |
O8 | 0.3719 (11) | 0.5637 (10) | 0.0178 (2) | 0.126 (2) | |
O9 | 0.5279 (9) | 0.7712 (9) | −0.01627 (17) | 0.106 (2) | |
O10 | 0.3128 (9) | 0.7616 (9) | 0.0127 (4) | 0.155 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0387 (4) | 0.0429 (4) | 0.0466 (4) | 0.0197 (3) | 0.0031 (3) | −0.0004 (3) |
S1 | 0.0593 (9) | 0.0608 (10) | 0.0587 (10) | 0.0332 (8) | 0.0139 (8) | 0.0024 (8) |
N1 | 0.047 (3) | 0.054 (3) | 0.049 (3) | 0.026 (2) | 0.004 (2) | −0.001 (2) |
O1 | 0.046 (2) | 0.059 (2) | 0.050 (2) | 0.025 (2) | −0.0055 (19) | −0.010 (2) |
O2 | 0.060 (3) | 0.066 (3) | 0.049 (2) | 0.038 (2) | −0.003 (2) | 0.000 (2) |
O3 | 0.075 (3) | 0.066 (3) | 0.079 (3) | 0.045 (3) | 0.021 (3) | 0.022 (2) |
O4 | 0.052 (3) | 0.064 (3) | 0.119 (4) | 0.011 (2) | 0.015 (3) | −0.037 (3) |
C1 | 0.078 (5) | 0.082 (5) | 0.050 (4) | 0.048 (4) | −0.004 (3) | −0.014 (4) |
C2 | 0.070 (5) | 0.080 (5) | 0.069 (5) | 0.040 (4) | −0.019 (4) | −0.023 (4) |
C3 | 0.042 (3) | 0.067 (4) | 0.086 (6) | 0.024 (3) | −0.011 (3) | −0.009 (4) |
C4 | 0.041 (3) | 0.081 (5) | 0.077 (5) | 0.024 (4) | 0.012 (3) | 0.008 (4) |
C5 | 0.065 (4) | 0.082 (5) | 0.047 (4) | 0.035 (4) | 0.005 (3) | 0.003 (3) |
C6 | 0.068 (4) | 0.079 (5) | 0.053 (4) | 0.040 (4) | 0.007 (3) | 0.018 (4) |
C7 | 0.070 (4) | 0.077 (5) | 0.076 (5) | 0.051 (4) | −0.014 (4) | −0.003 (4) |
C8 | 0.056 (4) | 0.071 (4) | 0.074 (5) | 0.040 (3) | 0.000 (3) | −0.008 (4) |
N2 | 0.060 (4) | 0.059 (4) | 0.082 (4) | 0.035 (3) | 0.010 (3) | 0.000 (3) |
O5 | 0.075 (4) | 0.099 (4) | 0.125 (6) | 0.040 (4) | 0.004 (3) | −0.051 (4) |
O6 | 0.100 (5) | 0.109 (5) | 0.160 (7) | 0.063 (4) | 0.061 (5) | 0.016 (5) |
O7 | 0.122 (6) | 0.101 (5) | 0.176 (8) | 0.005 (5) | 0.031 (6) | −0.062 (5) |
N3 | 0.053 (3) | 0.047 (3) | 0.094 (5) | 0.020 (3) | 0.005 (3) | −0.012 (3) |
O8 | 0.131 (6) | 0.093 (5) | 0.151 (6) | 0.055 (5) | −0.003 (5) | 0.022 (5) |
O9 | 0.097 (5) | 0.103 (5) | 0.099 (5) | 0.036 (4) | 0.031 (4) | 0.014 (4) |
O10 | 0.077 (4) | 0.093 (5) | 0.301 (13) | 0.048 (4) | 0.037 (6) | −0.031 (6) |
Geometric parameters (Å, º) top
Ni1—O4 | 2.028 (5) | O2—C6 | 1.432 (8) |
Ni1—O3 | 2.029 (5) | O2—C7 | 1.438 (8) |
Ni1—O2 | 2.073 (4) | C1—C2 | 1.495 (9) |
Ni1—N1 | 2.082 (5) | C3—C4 | 1.494 (10) |
Ni1—O1 | 2.082 (4) | C5—C6 | 1.502 (11) |
Ni1—S1 | 2.4185 (17) | C7—C8 | 1.488 (10) |
S1—C8 | 1.795 (7) | N2—O7 | 1.187 (10) |
S1—C1 | 1.821 (7) | N2—O6 | 1.200 (8) |
N1—C5 | 1.473 (9) | N2—O5 | 1.225 (8) |
N1—C4 | 1.476 (8) | N3—O10 | 1.166 (10) |
O1—C3 | 1.426 (7) | N3—O8 | 1.190 (9) |
O1—C2 | 1.438 (8) | N3—O9 | 1.245 (9) |
| | | |
O4—Ni1—O3 | 91.9 (2) | C3—O1—C2 | 114.3 (5) |
O4—Ni1—O2 | 87.0 (2) | C3—O1—Ni1 | 107.9 (4) |
O3—Ni1—O2 | 178.8 (2) | C2—O1—Ni1 | 114.0 (4) |
O4—Ni1—N1 | 99.1 (2) | C6—O2—C7 | 115.0 (5) |
O3—Ni1—N1 | 98.0 (2) | C6—O2—Ni1 | 110.4 (4) |
O2—Ni1—N1 | 82.75 (18) | C7—O2—Ni1 | 116.5 (4) |
O4—Ni1—O1 | 178.5 (2) | C2—C1—S1 | 112.2 (5) |
O3—Ni1—O1 | 89.45 (19) | O1—C2—C1 | 107.9 (6) |
O2—Ni1—O1 | 91.66 (17) | O1—C3—C4 | 106.8 (5) |
N1—Ni1—O1 | 80.19 (17) | N1—C4—C3 | 112.7 (5) |
O4—Ni1—S1 | 98.07 (15) | N1—C5—C6 | 110.1 (6) |
O3—Ni1—S1 | 95.33 (15) | O2—C6—C5 | 107.1 (6) |
O2—Ni1—S1 | 84.27 (12) | O2—C7—C8 | 108.8 (6) |
N1—Ni1—S1 | 157.83 (14) | C7—C8—S1 | 114.9 (5) |
O1—Ni1—S1 | 82.31 (12) | O7—N2—O6 | 119.4 (8) |
C8—S1—C1 | 101.7 (4) | O7—N2—O5 | 118.9 (7) |
C8—S1—Ni1 | 94.4 (2) | O6—N2—O5 | 121.7 (8) |
C1—S1—Ni1 | 96.9 (2) | O10—N3—O8 | 120.2 (9) |
C5—N1—C4 | 112.3 (6) | O10—N3—O9 | 123.9 (8) |
C5—N1—Ni1 | 105.1 (4) | O8—N3—O9 | 115.9 (8) |
C4—N1—Ni1 | 110.0 (4) | | |
| | | |
O4—Ni1—S1—C8 | 78.3 (3) | O4—Ni1—O2—C6 | 109.6 (4) |
O3—Ni1—S1—C8 | 171.0 (3) | O3—Ni1—O2—C6 | 137 (9) |
O2—Ni1—S1—C8 | −7.8 (3) | N1—Ni1—O2—C6 | 10.0 (4) |
N1—Ni1—S1—C8 | −62.2 (4) | O1—Ni1—O2—C6 | −69.9 (4) |
O1—Ni1—S1—C8 | −100.2 (3) | S1—Ni1—O2—C6 | −152.0 (4) |
O4—Ni1—S1—C1 | −179.3 (3) | O4—Ni1—O2—C7 | −116.8 (5) |
O3—Ni1—S1—C1 | −86.5 (3) | O3—Ni1—O2—C7 | −89 (9) |
O2—Ni1—S1—C1 | 94.6 (3) | N1—Ni1—O2—C7 | 143.7 (5) |
N1—Ni1—S1—C1 | 40.3 (5) | O1—Ni1—O2—C7 | 63.8 (4) |
O1—Ni1—S1—C1 | 2.2 (3) | S1—Ni1—O2—C7 | −18.3 (4) |
O4—Ni1—N1—C5 | −66.7 (5) | C8—S1—C1—C2 | 121.5 (6) |
O3—Ni1—N1—C5 | −160.0 (4) | Ni1—S1—C1—C2 | 25.5 (6) |
O2—Ni1—N1—C5 | 19.0 (4) | C3—O1—C2—C1 | −178.5 (6) |
O1—Ni1—N1—C5 | 112.0 (4) | Ni1—O1—C2—C1 | 56.8 (7) |
S1—Ni1—N1—C5 | 73.6 (6) | S1—C1—C2—O1 | −53.0 (8) |
O4—Ni1—N1—C4 | 172.2 (4) | C2—O1—C3—C4 | −178.7 (6) |
O3—Ni1—N1—C4 | 79.0 (5) | Ni1—O1—C3—C4 | −50.7 (6) |
O2—Ni1—N1—C4 | −102.0 (4) | C5—N1—C4—C3 | −132.8 (6) |
O1—Ni1—N1—C4 | −9.1 (4) | Ni1—N1—C4—C3 | −16.2 (7) |
S1—Ni1—N1—C4 | −47.4 (6) | O1—C3—C4—N1 | 44.5 (8) |
O4—Ni1—O1—C3 | 95 (7) | C4—N1—C5—C6 | 74.6 (7) |
O3—Ni1—O1—C3 | −64.4 (4) | Ni1—N1—C5—C6 | −45.0 (7) |
O2—Ni1—O1—C3 | 116.2 (4) | C7—O2—C6—C5 | −170.8 (5) |
N1—Ni1—O1—C3 | 33.8 (4) | Ni1—O2—C6—C5 | −36.4 (7) |
S1—Ni1—O1—C3 | −159.8 (4) | N1—C5—C6—O2 | 55.4 (8) |
O4—Ni1—O1—C2 | −137 (7) | C6—O2—C7—C8 | 175.4 (5) |
O3—Ni1—O1—C2 | 63.7 (4) | Ni1—O2—C7—C8 | 43.8 (6) |
O2—Ni1—O1—C2 | −115.8 (4) | O2—C7—C8—S1 | −52.6 (7) |
N1—Ni1—O1—C2 | 161.9 (4) | C1—S1—C8—C7 | −64.2 (6) |
S1—Ni1—O1—C2 | −31.8 (4) | Ni1—S1—C8—C7 | 33.8 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O7 | 0.91 | 2.44 | 3.177 (9) | 139 |
N1—H1···O8 | 0.91 | 2.56 | 3.180 (9) | 126 |
O3—H31···O9 | 0.96 | 2.02 | 2.779 (8) | 134 |
O3—H31···O8 | 0.96 | 2.65 | 3.244 (10) | 121 |
O3—H32···O5i | 0.96 | 2.00 | 2.734 (7) | 132 |
O3—H32···O7i | 0.96 | 2.40 | 3.347 (9) | 171 |
O3—H32···N2i | 0.96 | 2.55 | 3.465 (8) | 160 |
O4—H41···O6 | 0.96 | 1.99 | 2.763 (9) | 136 |
O4—H41···O7 | 0.96 | 2.32 | 3.174 (10) | 149 |
O4—H41···N2 | 0.96 | 2.49 | 3.380 (8) | 154 |
O4—H42···O10ii | 0.96 | 2.14 | 2.704 (8) | 116 |
Symmetry codes: (i) x−y+1, x, z−1/6; (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 = 499.84 | Dx = 2.381 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.245 (3) Å | Cell parameters from 25 reflections |
b = 11.927 (2) Å | θ = 10–14° |
c = 14.272 (5) Å | µ = 11.09 mm−1 |
β = 96.60 (2)° | T = 275 K |
V = 1394.2 (7) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.20 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | 2082 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω–2θ scans | h = 0→9 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→14 |
Tmin = 0.055, Tmax = 0.109 | l = −16→16 |
2623 measured reflections | 3 standard reflections every 120 min |
2444 independent reflections | intensity decay: <5% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.087 | Calculated w = 1/[σ2(Fo2) + (0.0622P)2 + 1.3329P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2444 reflections | Δρmax = 1.46 e Å−3 |
191 parameters | Δρmin = −3.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: Patterson | Extinction 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 | x | y | z | Uiso*/Ueq | |
Hg1 | 0.07460 (3) | 0.140753 (19) | 0.310704 (17) | 0.03087 (15) | |
N1 | 0.1946 (7) | 0.2309 (5) | 0.4327 (4) | 0.0360 (13) | |
H1 | 0.2046 | 0.1810 | 0.4813 | 0.043* | |
O1 | −0.0481 (6) | 0.3365 (4) | 0.3058 (3) | 0.0365 (11) | |
O2 | 0.1265 (6) | 0.2609 (4) | 0.1614 (3) | 0.0402 (11) | |
O3 | 0.3852 (6) | 0.1594 (4) | 0.2794 (4) | 0.0408 (12) | |
C1 | 0.0879 (9) | 0.3214 (7) | 0.4604 (5) | 0.0415 (17) | |
H1A | 0.1454 | 0.3634 | 0.5121 | 0.050* | |
H1B | −0.0084 | 0.2886 | 0.4825 | 0.050* | |
C2 | 0.0362 (10) | 0.4001 (6) | 0.3802 (5) | 0.0423 (17) | |
H2A | −0.0347 | 0.4580 | 0.4006 | 0.051* | |
H2B | 0.1311 | 0.4359 | 0.3590 | 0.051* | |
C3 | −0.0593 (9) | 0.3885 (7) | 0.2161 (6) | 0.0436 (18) | |
H3A | −0.0837 | 0.4675 | 0.2230 | 0.052* | |
H3B | −0.1490 | 0.3552 | 0.1756 | 0.052* | |
C4 | 0.0939 (11) | 0.3775 (6) | 0.1700 (6) | 0.0448 (19) | |
H4A | 0.0802 | 0.4125 | 0.1083 | 0.054* | |
H4B | 0.1839 | 0.4138 | 0.2080 | 0.054* | |
C5 | 0.2792 (10) | 0.2355 (7) | 0.1308 (6) | 0.0487 (19) | |
H5A | 0.3011 | 0.2885 | 0.0822 | 0.058* | |
H5B | 0.2743 | 0.1612 | 0.1030 | 0.058* | |
C6 | 0.4172 (9) | 0.2394 (7) | 0.2095 (6) | 0.048 (2) | |
H6A | 0.5195 | 0.2219 | 0.1854 | 0.058* | |
H6B | 0.4256 | 0.3139 | 0.2369 | 0.058* | |
C7 | 0.4575 (9) | 0.1861 (7) | 0.3726 (6) | 0.050 (2) | |
H7A | 0.5662 | 0.2156 | 0.3691 | 0.060* | |
H7B | 0.4684 | 0.1178 | 0.4097 | 0.060* | |
C8 | 0.3621 (8) | 0.2691 (6) | 0.4215 (6) | 0.0415 (17) | |
H8A | 0.4195 | 0.2845 | 0.4834 | 0.050* | |
H8B | 0.3556 | 0.3387 | 0.3861 | 0.050* | |
N2 | −0.0985 (7) | 0.0310 (5) | 0.1530 (4) | 0.0385 (13) | |
O4 | 0.0454 (6) | 0.0177 (4) | 0.1985 (4) | 0.0425 (12) | |
O5 | −0.1850 (7) | 0.1050 (5) | 0.1810 (4) | 0.0574 (15) | |
O6 | −0.1402 (8) | −0.0291 (6) | 0.0863 (4) | 0.0672 (18) | |
N3 | −0.1663 (6) | 0.0164 (5) | 0.4295 (4) | 0.0332 (13) | |
O7 | −0.2714 (6) | −0.0165 (4) | 0.4780 (4) | 0.0458 (13) | |
O8 | −0.1597 (6) | 0.1178 (4) | 0.4103 (4) | 0.0463 (13) | |
O9 | −0.0676 (7) | −0.0483 (5) | 0.4004 (4) | 0.0545 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Hg1 | 0.0312 (2) | 0.0282 (2) | 0.0330 (2) | −0.00259 (9) | 0.00311 (11) | −0.00102 (10) |
N1 | 0.043 (3) | 0.040 (3) | 0.024 (3) | −0.008 (3) | 0.002 (2) | 0.009 (2) |
O1 | 0.039 (3) | 0.031 (2) | 0.038 (3) | 0.000 (2) | −0.001 (2) | −0.004 (2) |
O2 | 0.050 (3) | 0.037 (3) | 0.036 (3) | 0.005 (2) | 0.010 (2) | 0.003 (2) |
O3 | 0.032 (3) | 0.033 (3) | 0.058 (3) | 0.005 (2) | 0.008 (2) | 0.005 (2) |
C1 | 0.046 (4) | 0.045 (4) | 0.033 (4) | −0.006 (4) | 0.008 (3) | −0.011 (3) |
C2 | 0.052 (5) | 0.029 (4) | 0.045 (4) | 0.004 (3) | 0.001 (3) | −0.012 (3) |
C3 | 0.047 (4) | 0.038 (4) | 0.043 (4) | 0.009 (3) | −0.007 (3) | 0.008 (3) |
C4 | 0.065 (5) | 0.032 (4) | 0.037 (4) | 0.006 (3) | 0.005 (4) | 0.010 (3) |
C5 | 0.053 (5) | 0.047 (4) | 0.049 (4) | 0.004 (4) | 0.022 (4) | 0.003 (4) |
C6 | 0.042 (4) | 0.044 (4) | 0.062 (5) | 0.003 (3) | 0.024 (4) | 0.014 (4) |
C7 | 0.029 (4) | 0.052 (5) | 0.066 (5) | 0.007 (3) | −0.003 (3) | 0.014 (4) |
C8 | 0.029 (4) | 0.039 (4) | 0.054 (4) | −0.001 (3) | −0.005 (3) | 0.004 (3) |
N2 | 0.038 (3) | 0.038 (3) | 0.039 (3) | 0.000 (3) | 0.001 (3) | 0.002 (3) |
O4 | 0.044 (3) | 0.035 (3) | 0.046 (3) | 0.004 (2) | −0.007 (2) | −0.002 (2) |
O5 | 0.047 (3) | 0.057 (3) | 0.067 (4) | 0.013 (3) | 0.003 (3) | −0.011 (3) |
O6 | 0.060 (4) | 0.075 (4) | 0.062 (4) | −0.003 (3) | −0.010 (3) | −0.035 (3) |
N3 | 0.026 (3) | 0.041 (3) | 0.030 (3) | 0.002 (2) | −0.007 (2) | 0.001 (3) |
O7 | 0.044 (3) | 0.046 (3) | 0.047 (3) | −0.009 (2) | 0.007 (2) | 0.015 (2) |
O8 | 0.040 (3) | 0.040 (3) | 0.059 (3) | 0.001 (2) | 0.006 (3) | 0.018 (3) |
O9 | 0.047 (3) | 0.059 (4) | 0.054 (3) | 0.017 (3) | −0.008 (3) | −0.017 (3) |
Geometric parameters (Å, º) top
Hg1—O4 | 2.166 (5) | O2—C4 | 1.424 (8) |
Hg1—N1 | 2.184 (5) | O3—C6 | 1.427 (9) |
Hg1—O8 | 2.541 (5) | O3—C7 | 1.429 (10) |
Hg1—O1 | 2.543 (5) | C1—C2 | 1.504 (11) |
Hg1—O2 | 2.644 (5) | C3—C4 | 1.495 (11) |
Hg1—O3 | 2.659 (5) | C5—C6 | 1.505 (11) |
Hg1—O5 | 2.698 (6) | C7—C8 | 1.488 (11) |
Hg1—O9 | 2.906 (6) | N2—O6 | 1.208 (8) |
N1—C1 | 1.474 (9) | N2—O5 | 1.231 (8) |
N1—C8 | 1.480 (8) | N2—O4 | 1.295 (7) |
O1—C3 | 1.415 (9) | N3—O9 | 1.228 (7) |
O1—C2 | 1.420 (8) | N3—O7 | 1.234 (7) |
O2—C5 | 1.413 (9) | N3—O8 | 1.243 (7) |
| | | |
O4—Hg1—N1 | 157.7 (2) | C1—N1—Hg1 | 110.1 (4) |
O4—Hg1—O8 | 108.29 (19) | C8—N1—Hg1 | 114.1 (4) |
N1—Hg1—O8 | 84.87 (19) | C3—O1—C2 | 114.7 (6) |
O4—Hg1—O1 | 126.29 (17) | C3—O1—Hg1 | 114.3 (4) |
N1—Hg1—O1 | 73.28 (18) | C2—O1—Hg1 | 108.1 (4) |
O8—Hg1—O1 | 77.79 (16) | C5—O2—C4 | 114.9 (6) |
O4—Hg1—O2 | 77.63 (18) | C5—O2—Hg1 | 111.4 (4) |
N1—Hg1—O2 | 105.99 (18) | C4—O2—Hg1 | 114.2 (4) |
O8—Hg1—O2 | 135.48 (16) | C6—O3—C7 | 114.2 (6) |
O1—Hg1—O2 | 65.19 (15) | C6—O3—Hg1 | 115.6 (4) |
O4—Hg1—O3 | 87.69 (18) | C7—O3—Hg1 | 99.7 (4) |
N1—Hg1—O3 | 74.71 (19) | N1—C1—C2 | 112.3 (6) |
O8—Hg1—O3 | 155.73 (18) | O1—C2—C1 | 107.9 (6) |
O1—Hg1—O3 | 107.86 (15) | O1—C3—C4 | 112.9 (6) |
O2—Hg1—O3 | 64.61 (16) | O2—C4—C3 | 107.6 (6) |
O4—Hg1—O5 | 51.21 (18) | O2—C5—C6 | 112.7 (6) |
N1—Hg1—O5 | 151.11 (19) | O3—C6—C5 | 108.5 (6) |
O8—Hg1—O5 | 76.85 (19) | O3—C7—C8 | 113.5 (6) |
O1—Hg1—O5 | 81.04 (17) | N1—C8—C7 | 113.3 (6) |
O2—Hg1—O5 | 73.85 (18) | O6—N2—O5 | 123.9 (7) |
O3—Hg1—O5 | 126.98 (18) | O6—N2—O4 | 118.9 (6) |
O4—Hg1—O9 | 77.50 (17) | O5—N2—O4 | 117.1 (6) |
N1—Hg1—O9 | 101.51 (17) | N2—O4—Hg1 | 107.8 (4) |
O8—Hg1—O9 | 45.49 (16) | N2—O5—Hg1 | 83.9 (4) |
O1—Hg1—O9 | 123.06 (15) | O9—N3—O7 | 121.7 (6) |
O2—Hg1—O9 | 152.46 (15) | O9—N3—O8 | 119.3 (6) |
O3—Hg1—O9 | 125.73 (14) | O7—N3—O8 | 118.9 (6) |
O5—Hg1—O9 | 81.42 (18) | N3—O8—Hg1 | 106.5 (4) |
C1—N1—C8 | 113.3 (6) | N3—O9—Hg1 | 88.7 (4) |
| | | |
O4—Hg1—N1—C1 | 178.8 (5) | C8—N1—C1—C2 | 73.7 (7) |
O8—Hg1—N1—C1 | −53.6 (4) | Hg1—N1—C1—C2 | −55.4 (7) |
O1—Hg1—N1—C1 | 25.2 (4) | C3—O1—C2—C1 | −160.8 (6) |
O2—Hg1—N1—C1 | 82.4 (4) | Hg1—O1—C2—C1 | −32.0 (7) |
O3—Hg1—N1—C1 | 139.6 (5) | N1—C1—C2—O1 | 59.1 (8) |
O5—Hg1—N1—C1 | −3.1 (7) | C2—O1—C3—C4 | 79.6 (8) |
O9—Hg1—N1—C1 | −96.1 (4) | Hg1—O1—C3—C4 | −46.1 (8) |
O4—Hg1—N1—C8 | 50.0 (7) | C5—O2—C4—C3 | −171.8 (6) |
O8—Hg1—N1—C8 | 177.7 (5) | Hg1—O2—C4—C3 | −41.3 (7) |
O1—Hg1—N1—C8 | −103.5 (5) | O1—C3—C4—O2 | 58.4 (9) |
O2—Hg1—N1—C8 | −46.4 (5) | C4—O2—C5—C6 | 81.5 (8) |
O3—Hg1—N1—C8 | 10.9 (4) | Hg1—O2—C5—C6 | −50.3 (7) |
O5—Hg1—N1—C8 | −131.8 (5) | C7—O3—C6—C5 | −152.9 (6) |
O9—Hg1—N1—C8 | 135.1 (4) | Hg1—O3—C6—C5 | −38.0 (7) |
O4—Hg1—O1—C3 | −34.5 (5) | O2—C5—C6—O3 | 60.0 (9) |
N1—Hg1—O1—C3 | 133.4 (5) | C6—O3—C7—C8 | 81.0 (8) |
O8—Hg1—O1—C3 | −138.3 (5) | Hg1—O3—C7—C8 | −42.9 (7) |
O2—Hg1—O1—C3 | 16.3 (4) | C1—N1—C8—C7 | −166.5 (6) |
O3—Hg1—O1—C3 | 66.1 (5) | Hg1—N1—C8—C7 | −39.4 (7) |
O5—Hg1—O1—C3 | −59.9 (5) | O3—C7—C8—N1 | 60.0 (9) |
O9—Hg1—O1—C3 | −133.5 (4) | O6—N2—O4—Hg1 | 179.4 (6) |
O4—Hg1—O1—C2 | −163.5 (4) | O5—N2—O4—Hg1 | −0.7 (7) |
N1—Hg1—O1—C2 | 4.4 (4) | N1—Hg1—O4—N2 | 179.2 (5) |
O8—Hg1—O1—C2 | 92.7 (4) | O8—Hg1—O4—N2 | 55.4 (4) |
O2—Hg1—O1—C2 | −112.7 (5) | O1—Hg1—O4—N2 | −32.7 (5) |
O3—Hg1—O1—C2 | −62.9 (5) | O2—Hg1—O4—N2 | −78.8 (4) |
O5—Hg1—O1—C2 | 171.0 (5) | O3—Hg1—O4—N2 | −143.3 (4) |
O9—Hg1—O1—C2 | 97.4 (4) | O5—Hg1—O4—N2 | 0.3 (4) |
O4—Hg1—O2—C5 | −72.8 (5) | O9—Hg1—O4—N2 | 89.3 (4) |
N1—Hg1—O2—C5 | 84.5 (5) | O6—N2—O5—Hg1 | −179.6 (7) |
O8—Hg1—O2—C5 | −176.4 (4) | O4—N2—O5—Hg1 | 0.5 (5) |
O1—Hg1—O2—C5 | 146.9 (5) | O4—Hg1—O5—N2 | −0.4 (4) |
O3—Hg1—O2—C5 | 20.5 (4) | N1—Hg1—O5—N2 | −179.5 (4) |
O5—Hg1—O2—C5 | −125.6 (5) | O8—Hg1—O5—N2 | −127.3 (4) |
O9—Hg1—O2—C5 | −98.7 (5) | O1—Hg1—O5—N2 | 153.2 (4) |
O4—Hg1—O2—C4 | 155.0 (5) | O2—Hg1—O5—N2 | 86.6 (4) |
N1—Hg1—O2—C4 | −47.7 (5) | O3—Hg1—O5—N2 | 47.6 (5) |
O8—Hg1—O2—C4 | 51.4 (6) | O9—Hg1—O5—N2 | −81.2 (4) |
O1—Hg1—O2—C4 | 14.8 (5) | O9—N3—O8—Hg1 | 0.4 (7) |
O3—Hg1—O2—C4 | −111.6 (5) | O7—N3—O8—Hg1 | 179.9 (4) |
O5—Hg1—O2—C4 | 102.2 (5) | O4—Hg1—O8—N3 | 49.6 (4) |
O9—Hg1—O2—C4 | 129.2 (5) | N1—Hg1—O8—N3 | −111.9 (4) |
O4—Hg1—O3—C6 | 87.9 (5) | O1—Hg1—O8—N3 | 174.1 (4) |
N1—Hg1—O3—C6 | −105.9 (5) | O2—Hg1—O8—N3 | 140.5 (4) |
O8—Hg1—O3—C6 | −139.6 (5) | O3—Hg1—O8—N3 | −79.4 (6) |
O1—Hg1—O3—C6 | −39.6 (5) | O5—Hg1—O8—N3 | 90.6 (4) |
O2—Hg1—O3—C6 | 10.5 (5) | O9—Hg1—O8—N3 | −0.2 (3) |
O5—Hg1—O3—C6 | 52.6 (5) | O7—N3—O9—Hg1 | −179.8 (5) |
O9—Hg1—O3—C6 | 160.7 (5) | O8—N3—O9—Hg1 | −0.4 (6) |
O4—Hg1—O3—C7 | −149.1 (4) | O4—Hg1—O9—N3 | −131.7 (4) |
N1—Hg1—O3—C7 | 17.0 (4) | N1—Hg1—O9—N3 | 71.1 (4) |
O8—Hg1—O3—C7 | −16.7 (6) | O8—Hg1—O9—N3 | 0.2 (3) |
O1—Hg1—O3—C7 | 83.3 (4) | O1—Hg1—O9—N3 | −6.4 (4) |
O2—Hg1—O3—C7 | 133.5 (4) | O2—Hg1—O9—N3 | −105.9 (4) |
O5—Hg1—O3—C7 | 175.5 (4) | O3—Hg1—O9—N3 | 150.4 (3) |
O9—Hg1—O3—C7 | −76.3 (4) | O5—Hg1—O9—N3 | −79.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O7i | 0.91 | 2.10 | 2.895 (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 = 378.84 | F(000) = 394 |
Triclinic, P1 | Dx = 1.707 Mg m−3 |
a = 8.6167 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3975 (8) Å | Cell parameters from 25 reflections |
c = 10.118 (1) Å | θ = 10–14° |
α = 95.627 (8)° | µ = 1.53 mm−1 |
β = 112.107 (9)° | T = 295 K |
γ = 99.509 (9)° | Prism, blue |
V = 737.05 (12) Å3 | 0.60 × 0.60 × 0.30 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | 2392 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 2.2° |
ω–2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −11→11 |
Tmin = 0.401, Tmax = 0.632 | l = −12→11 |
2774 measured reflections | 3 standard reflections every 120 min |
2586 independent reflections | intensity decay: <5% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.068 | Calculated w = 1/[σ2(Fo2) + (0.0343P)2 + 0.4836P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2586 reflections | Δρmax = 0.36 e Å−3 |
200 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: Patterson | Extinction 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 | x | y | z | Uiso*/Ueq | |
Cu1 | 0.21252 (3) | 0.31381 (3) | 0.28989 (3) | 0.02718 (12) | |
N1 | 0.4259 (2) | 0.3414 (2) | 0.2459 (2) | 0.0323 (4) | |
H1 | 0.4852 | 0.4361 | 0.2790 | 0.039* | |
N2 | 0.2809 (2) | 0.13935 (19) | 0.3690 (2) | 0.0324 (4) | |
H2 | 0.3292 | 0.1633 | 0.4674 | 0.039* | |
N3 | −0.0304 (2) | 0.2185 (2) | 0.2627 (2) | 0.0358 (4) | |
H3 | −0.0734 | 0.2846 | 0.3028 | 0.043* | |
O1 | 0.1719 (2) | 0.51182 (16) | 0.26897 (18) | 0.0363 (4) | |
O2 | 0.0888 (2) | 0.22036 (17) | 0.04050 (17) | 0.0363 (4) | |
H21 | 0.1158 | 0.5411 | 0.3073 | 0.044* | |
H22 | 0.2444 | 0.5720 | 0.2825 | 0.044* | |
C1 | 0.2013 (3) | 0.3174 (3) | −0.0028 (3) | 0.0417 (6) | |
H1A | 0.1890 | 0.4175 | 0.0144 | 0.050* | |
H1B | 0.1748 | 0.2892 | −0.1051 | 0.050* | |
C2 | 0.3804 (3) | 0.3044 (3) | 0.0871 (3) | 0.0414 (6) | |
H2A | 0.3916 | 0.2050 | 0.0642 | 0.050* | |
H2B | 0.4609 | 0.3695 | 0.0621 | 0.050* | |
C3 | 0.5307 (3) | 0.2438 (3) | 0.3283 (3) | 0.0401 (5) | |
H3A | 0.5948 | 0.2912 | 0.4286 | 0.048* | |
H3B | 0.6118 | 0.2239 | 0.2874 | 0.048* | |
C4 | 0.4125 (3) | 0.1017 (3) | 0.3205 (3) | 0.0409 (5) | |
H4A | 0.3585 | 0.0481 | 0.2219 | 0.049* | |
H4B | 0.4769 | 0.0408 | 0.3823 | 0.049* | |
C5 | 0.1237 (3) | 0.0239 (2) | 0.3266 (3) | 0.0409 (5) | |
H5A | 0.1456 | −0.0504 | 0.3873 | 0.049* | |
H5B | 0.0864 | −0.0225 | 0.2265 | 0.049* | |
C6 | −0.0126 (3) | 0.0955 (3) | 0.3451 (3) | 0.0428 (6) | |
H6A | −0.1210 | 0.0246 | 0.3095 | 0.051* | |
H6B | 0.0195 | 0.1322 | 0.4469 | 0.051* | |
C7 | −0.1451 (3) | 0.1706 (3) | 0.1063 (3) | 0.0458 (6) | |
H7A | −0.2583 | 0.1877 | 0.0903 | 0.055* | |
H7B | −0.1566 | 0.0662 | 0.0795 | 0.055* | |
C8 | −0.0768 (3) | 0.2509 (3) | 0.0112 (3) | 0.0429 (6) | |
H8A | −0.1519 | 0.2168 | −0.0901 | 0.051* | |
H8B | −0.0677 | 0.3554 | 0.0342 | 0.051* | |
N4 | 0.1509 (2) | 0.4333 (2) | 0.6302 (2) | 0.0361 (4) | |
O3 | 0.2037 (2) | 0.5294 (2) | 0.73981 (19) | 0.0467 (4) | |
O4 | −0.0026 (2) | 0.3634 (2) | 0.5789 (2) | 0.0533 (5) | |
O5 | 0.2479 (2) | 0.4077 (2) | 0.56979 (19) | 0.0444 (4) | |
N5 | 0.4988 (2) | 0.2483 (2) | 0.7541 (2) | 0.0384 (5) | |
O6 | 0.5639 (2) | 0.25468 (19) | 0.66193 (18) | 0.0443 (4) | |
O7 | 0.3773 (3) | 0.1476 (2) | 0.7311 (3) | 0.0823 (8) | |
O8 | 0.5587 (3) | 0.3456 (3) | 0.8614 (2) | 0.0633 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.02852 (17) | 0.02262 (16) | 0.03316 (17) | 0.00233 (10) | 0.01675 (11) | 0.00476 (10) |
N1 | 0.0321 (9) | 0.0310 (9) | 0.0381 (10) | 0.0037 (8) | 0.0198 (8) | 0.0071 (8) |
N2 | 0.0409 (10) | 0.0270 (9) | 0.0319 (9) | 0.0043 (8) | 0.0187 (8) | 0.0056 (7) |
N3 | 0.0340 (10) | 0.0297 (9) | 0.0456 (11) | 0.0013 (8) | 0.0223 (9) | −0.0021 (8) |
O1 | 0.0398 (9) | 0.0259 (8) | 0.0523 (10) | 0.0050 (6) | 0.0295 (8) | 0.0060 (7) |
O2 | 0.0379 (8) | 0.0367 (8) | 0.0354 (8) | 0.0090 (7) | 0.0150 (7) | 0.0076 (7) |
C1 | 0.0535 (15) | 0.0449 (14) | 0.0315 (12) | 0.0096 (11) | 0.0214 (11) | 0.0125 (10) |
C2 | 0.0482 (14) | 0.0482 (14) | 0.0404 (13) | 0.0101 (11) | 0.0308 (11) | 0.0119 (11) |
C3 | 0.0328 (12) | 0.0470 (14) | 0.0459 (13) | 0.0119 (10) | 0.0194 (10) | 0.0123 (11) |
C4 | 0.0471 (14) | 0.0360 (12) | 0.0492 (14) | 0.0181 (11) | 0.0245 (11) | 0.0137 (10) |
C5 | 0.0526 (14) | 0.0240 (11) | 0.0495 (14) | 0.0007 (10) | 0.0272 (12) | 0.0077 (10) |
C6 | 0.0496 (14) | 0.0318 (12) | 0.0525 (14) | −0.0058 (10) | 0.0332 (12) | 0.0042 (10) |
C7 | 0.0299 (12) | 0.0427 (14) | 0.0544 (15) | −0.0005 (10) | 0.0121 (11) | −0.0049 (11) |
C8 | 0.0371 (12) | 0.0422 (13) | 0.0395 (13) | 0.0104 (10) | 0.0056 (10) | −0.0006 (10) |
N4 | 0.0359 (10) | 0.0348 (10) | 0.0412 (11) | 0.0119 (8) | 0.0174 (9) | 0.0074 (8) |
O3 | 0.0497 (10) | 0.0459 (10) | 0.0427 (10) | 0.0072 (8) | 0.0206 (8) | −0.0034 (8) |
O4 | 0.0367 (9) | 0.0516 (11) | 0.0677 (12) | 0.0017 (8) | 0.0236 (9) | −0.0052 (9) |
O5 | 0.0399 (9) | 0.0496 (10) | 0.0497 (10) | 0.0144 (8) | 0.0242 (8) | 0.0014 (8) |
N5 | 0.0342 (10) | 0.0364 (11) | 0.0494 (12) | 0.0079 (8) | 0.0205 (9) | 0.0129 (9) |
O6 | 0.0470 (10) | 0.0474 (10) | 0.0399 (9) | 0.0017 (8) | 0.0236 (8) | 0.0034 (7) |
O7 | 0.0667 (14) | 0.0498 (12) | 0.144 (2) | −0.0096 (11) | 0.0681 (16) | 0.0114 (13) |
O8 | 0.0663 (13) | 0.0763 (14) | 0.0448 (11) | 0.0028 (11) | 0.0289 (10) | −0.0063 (10) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.9663 (15) | O2—C8 | 1.428 (3) |
Cu1—N2 | 1.9742 (18) | O2—C1 | 1.438 (3) |
Cu1—N1 | 2.0312 (18) | C1—C2 | 1.501 (4) |
Cu1—N3 | 2.0393 (18) | C3—C4 | 1.515 (3) |
Cu1—O2 | 2.3465 (16) | C5—C6 | 1.506 (4) |
Cu1—O5 | 2.7682 (17) | C7—C8 | 1.504 (4) |
N1—C3 | 1.486 (3) | N4—O3 | 1.241 (3) |
N1—C2 | 1.493 (3) | N4—O5 | 1.247 (2) |
N2—C4 | 1.472 (3) | N4—O4 | 1.257 (3) |
N2—C5 | 1.477 (3) | N5—O7 | 1.222 (3) |
N3—C6 | 1.484 (3) | N5—O8 | 1.228 (3) |
N3—C7 | 1.490 (3) | N5—O6 | 1.257 (3) |
| | | |
O1—Cu1—N2 | 163.92 (7) | C6—N3—C7 | 113.13 (19) |
O1—Cu1—N1 | 96.37 (7) | C6—N3—Cu1 | 105.76 (14) |
N2—Cu1—N1 | 86.73 (7) | C7—N3—Cu1 | 111.33 (14) |
O1—Cu1—N3 | 96.54 (7) | C8—O2—C1 | 116.32 (19) |
N2—Cu1—N3 | 86.40 (8) | C8—O2—Cu1 | 97.41 (13) |
N1—Cu1—N3 | 156.15 (8) | C1—O2—Cu1 | 98.62 (13) |
O1—Cu1—O2 | 95.29 (6) | O2—C1—C2 | 106.39 (19) |
N2—Cu1—O2 | 100.79 (7) | N1—C2—C1 | 112.69 (19) |
N1—Cu1—O2 | 79.83 (7) | N1—C3—C4 | 108.98 (19) |
N3—Cu1—O2 | 79.07 (7) | N2—C4—C3 | 107.58 (19) |
O1—Cu1—O5 | 81.64 (6) | N2—C5—C6 | 107.65 (18) |
N2—Cu1—O5 | 83.03 (6) | N3—C6—C5 | 108.79 (18) |
N1—Cu1—O5 | 118.63 (6) | N3—C7—C8 | 111.87 (19) |
N3—Cu1—O5 | 83.11 (7) | O2—C8—C7 | 106.0 (2) |
O2—Cu1—O5 | 161.46 (5) | O3—N4—O5 | 120.5 (2) |
C3—N1—C2 | 111.98 (18) | O3—N4—O4 | 119.46 (19) |
C3—N1—Cu1 | 105.46 (13) | O5—N4—O4 | 120.0 (2) |
C2—N1—Cu1 | 111.26 (14) | N4—O5—Cu1 | 136.44 (14) |
C4—N2—C5 | 115.95 (18) | O7—N5—O8 | 123.3 (2) |
C4—N2—Cu1 | 108.32 (13) | O7—N5—O6 | 118.5 (2) |
C5—N2—Cu1 | 107.86 (14) | O8—N5—O6 | 118.2 (2) |
| | | |
O1—Cu1—N1—C3 | 150.35 (14) | O5—Cu1—O2—C8 | 22.0 (2) |
N2—Cu1—N1—C3 | −13.81 (15) | O1—Cu1—O2—C1 | 60.69 (14) |
N3—Cu1—N1—C3 | −87.3 (2) | N2—Cu1—O2—C1 | −119.50 (14) |
O2—Cu1—N1—C3 | −115.40 (15) | N1—Cu1—O2—C1 | −34.85 (13) |
O5—Cu1—N1—C3 | 66.42 (16) | N3—Cu1—O2—C1 | 156.35 (14) |
O1—Cu1—N1—C2 | −88.04 (15) | O5—Cu1—O2—C1 | 140.12 (18) |
N2—Cu1—N1—C2 | 107.80 (16) | C8—O2—C1—C2 | 158.04 (19) |
N3—Cu1—N1—C2 | 34.4 (3) | Cu1—O2—C1—C2 | 55.31 (19) |
O2—Cu1—N1—C2 | 6.22 (14) | C3—N1—C2—C1 | 141.5 (2) |
O5—Cu1—N1—C2 | −171.96 (14) | Cu1—N1—C2—C1 | 23.7 (2) |
O1—Cu1—N2—C4 | −116.4 (2) | O2—C1—C2—N1 | −58.0 (3) |
N1—Cu1—N2—C4 | −14.67 (15) | C2—N1—C3—C4 | −81.9 (2) |
N3—Cu1—N2—C4 | 142.48 (16) | Cu1—N1—C3—C4 | 39.2 (2) |
O2—Cu1—N2—C4 | 64.33 (15) | C5—N2—C4—C3 | 161.1 (2) |
O5—Cu1—N2—C4 | −134.04 (15) | Cu1—N2—C4—C3 | 39.8 (2) |
O1—Cu1—N2—C5 | 117.4 (2) | N1—C3—C4—N2 | −53.5 (2) |
N1—Cu1—N2—C5 | −140.89 (15) | C4—N2—C5—C6 | −163.2 (2) |
N3—Cu1—N2—C5 | 16.26 (14) | Cu1—N2—C5—C6 | −41.6 (2) |
O2—Cu1—N2—C5 | −61.89 (15) | C7—N3—C6—C5 | 83.6 (2) |
O5—Cu1—N2—C5 | 99.74 (14) | Cu1—N3—C6—C5 | −38.5 (2) |
O1—Cu1—N3—C6 | −151.71 (14) | N2—C5—C6—N3 | 54.1 (3) |
N2—Cu1—N3—C6 | 12.42 (14) | C6—N3—C7—C8 | −140.1 (2) |
N1—Cu1—N3—C6 | 85.9 (2) | Cu1—N3—C7—C8 | −21.2 (2) |
O2—Cu1—N3—C6 | 114.14 (14) | C1—O2—C8—C7 | −161.99 (19) |
O5—Cu1—N3—C6 | −70.99 (14) | Cu1—O2—C8—C7 | −58.53 (18) |
O1—Cu1—N3—C7 | 85.03 (16) | N3—C7—C8—O2 | 58.9 (2) |
N2—Cu1—N3—C7 | −110.84 (16) | O3—N4—O5—Cu1 | −148.60 (17) |
N1—Cu1—N3—C7 | −37.3 (3) | O4—N4—O5—Cu1 | 30.2 (3) |
O2—Cu1—N3—C7 | −9.12 (15) | O1—Cu1—O5—N4 | 71.5 (2) |
O5—Cu1—N3—C7 | 165.75 (16) | N2—Cu1—O5—N4 | −113.4 (2) |
O1—Cu1—O2—C8 | −57.47 (14) | N1—Cu1—O5—N4 | 164.2 (2) |
N2—Cu1—O2—C8 | 122.34 (14) | N3—Cu1—O5—N4 | −26.2 (2) |
N1—Cu1—O2—C8 | −153.01 (14) | O2—Cu1—O5—N4 | −10.2 (3) |
N3—Cu1—O2—C8 | 38.19 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O5i | 0.91 | 2.36 | 3.153 (3) | 145 |
N1—H1···O8i | 0.91 | 2.61 | 3.234 (3) | 127 |
N2—H2···O6 | 0.91 | 2.19 | 2.994 (3) | 147 |
N2—H2···O7 | 0.91 | 2.56 | 3.428 (4) | 159 |
N2—H2···N5 | 0.91 | 2.68 | 3.582 (3) | 174 |
N3—H3···O3ii | 0.91 | 2.22 | 3.000 (3) | 143 |
N3—H3···O4 | 0.91 | 2.62 | 3.257 (3) | 127 |
O1—H21···O4ii | 0.79 | 2.00 | 2.788 (2) | 172 |
O1—H21···O3ii | 0.79 | 2.57 | 3.162 (2) | 133 |
O1—H21···N4ii | 0.79 | 2.64 | 3.398 (2) | 161 |
O1—H22···O6i | 0.73 | 1.98 | 2.709 (2) | 174 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |