Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100020308/bm1440sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020308/bm1440Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100020308/bm1440IIsup3.hkl |
CCDC references: 163881; 163882
For both compounds, data collection: SMART (Siemens, 1994); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C10H20N4O2·2H2O | Z = 1 |
Mr = 264.33 | F(000) = 144 |
Triclinic, P1 | Dx = 1.339 Mg m−3 |
a = 4.869 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.530 (5) Å | Cell parameters from 1077 reflections |
c = 9.150 (5) Å | θ = 3–20° |
α = 83.037 (10)° | µ = 0.10 mm−1 |
β = 88.727 (15)° | T = 200 K |
γ = 79.806 (10)° | Prism AUTHOR: please specify what kind, colourless |
V = 327.7 (3) Å3 | 0.48 × 0.10 × 0.10 mm |
Siemens SMART CCD area-detector diffractometer | 1118 independent reflections |
Radiation source: normal-focus sealed tube | 825 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 8.192 pixels mm-1 | θmax = 25.0°, θmin = 2.2° |
ω scans | h = −5→5 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −8→8 |
Tmin = 0.58, Tmax = 0.96 | l = −10→6 |
1627 measured reflections |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.073P)2] where P = (Fo2 + 2Fc2)/3 |
1118 reflections | (Δ/σ)max = 0.025 |
102 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Experimental. The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures with different φ angles for the crystal; each 10 s exposure covered 0.3° in ω. The crystal-to-detector distance was 5.0 cm. Coverage of the unique set is over 97% complete to at least 26° in θ. Crystal decay was found to be negligible by by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. The program SADABS (Sheldrick, 1996) can correct for factors other than absorption, including for any time-dependent changes: among other possible factors might be crystal incompletely bathed in the X-ray beam; formation of ice; severe absorption caused by oblique inclination of the beam and the fibre. Although no particular factor has been identified as being responsible for the discrepant range of transmission coefficients in the present case, it is clear that some factors or factors other than absorption were affecting the data, and refinement using the corrected data was more valid than that using the uncorrected set. Our estimate of the transmission coefficient range actually due to absorption would be of the order of 0.85–0.96. |
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. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating _R_factor_obs 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.5423 (3) | 0.2685 (2) | 0.44403 (15) | 0.0340 (4) | |
C1 | 0.3047 (4) | 0.2498 (3) | 0.4106 (2) | 0.0238 (5) | |
N2 | 0.1230 (4) | 0.1947 (2) | 0.51042 (19) | 0.0254 (4) | |
H2 | −0.054 (5) | 0.202 (3) | 0.479 (3) | 0.036 (6)* | |
C3 | 0.1882 (4) | 0.1570 (3) | 0.6668 (2) | 0.0271 (5) | |
H3A | 0.3912 | 0.1129 | 0.6793 | 0.033* | |
H3B | 0.0898 | 0.0596 | 0.7118 | 0.033* | |
C4 | 0.1038 (4) | 0.3241 (3) | 0.7458 (2) | 0.0269 (5) | |
H4A | 0.1868 | 0.3005 | 0.8456 | 0.032* | |
H4B | 0.1782 | 0.4273 | 0.6915 | 0.032* | |
N5 | −0.2007 (4) | 0.3733 (2) | 0.7581 (2) | 0.0251 (4) | |
H5A | −0.274 (4) | 0.384 (3) | 0.672 (2) | 0.028 (6)* | |
C6 | −0.2931 (4) | 0.5413 (3) | 0.8254 (2) | 0.0261 (5) | |
H6A | −0.2202 | 0.5223 | 0.9273 | 0.031* | |
H6B | −0.4993 | 0.5618 | 0.8319 | 0.031* | |
C7 | −0.2066 (4) | 0.7140 (3) | 0.7471 (2) | 0.0268 (5) | |
H7A | −0.2868 | 0.8185 | 0.7998 | 0.032* | |
H7B | −0.0009 | 0.7013 | 0.7495 | 0.032* | |
O2 | −0.2756 (5) | 0.0943 (3) | 0.9866 (2) | 0.0480 (5) | |
H2A | −0.291 (6) | 0.173 (4) | 0.909 (3) | 0.064 (9)* | |
H2B | −0.43 (2) | 0.059 (13) | 0.988 (12) | 0.15 (5)* | 0.50 |
H2C | −0.120 (9) | 0.033 (6) | 1.002 (5) | 0.030 (14)* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0201 (8) | 0.0440 (9) | 0.0370 (9) | −0.0073 (6) | −0.0037 (6) | 0.0017 (7) |
C1 | 0.0202 (11) | 0.0197 (10) | 0.0297 (12) | 0.0012 (8) | 0.0000 (8) | −0.0024 (9) |
N2 | 0.0221 (9) | 0.0266 (10) | 0.0276 (10) | −0.0052 (7) | −0.0010 (7) | −0.0023 (7) |
C3 | 0.0274 (11) | 0.0236 (11) | 0.0287 (12) | −0.0028 (9) | −0.0005 (9) | 0.0012 (9) |
C4 | 0.0244 (11) | 0.0281 (11) | 0.0279 (12) | −0.0055 (8) | −0.0023 (8) | −0.0005 (9) |
N5 | 0.0241 (9) | 0.0261 (10) | 0.0253 (10) | −0.0056 (7) | −0.0012 (7) | −0.0014 (8) |
C6 | 0.0238 (11) | 0.0299 (11) | 0.0241 (11) | −0.0036 (9) | 0.0023 (8) | −0.0033 (9) |
C7 | 0.0268 (11) | 0.0239 (11) | 0.0301 (12) | −0.0033 (8) | 0.0015 (9) | −0.0066 (9) |
O2 | 0.0498 (14) | 0.0418 (11) | 0.0459 (12) | −0.0043 (10) | 0.0047 (10) | 0.0144 (9) |
O1—C1 | 1.239 (2) | C6—C7 | 1.528 (3) |
C1—N2 | 1.339 (3) | C7—C1i | 1.507 (3) |
C1—C7i | 1.507 (3) | N2—H2A | 0.905 (10) |
N2—C3 | 1.456 (3) | N5—H5A | 0.864 (10) |
C3—C4 | 1.516 (3) | O2—H2A | 0.86 (1) |
C4—N5 | 1.469 (3) | O2—H2B | 0.85 (2) |
N5—C6 | 1.469 (3) | O2—H2C | 0.82 (2) |
O1—C1—N2 | 122.49 (19) | N5—C4—C3 | 111.71 (16) |
O1—C1—C7i | 121.17 (18) | C4—N5—C6 | 113.66 (15) |
N2—C1—C7i | 116.33 (17) | N5—C6—C7 | 116.61 (16) |
C1—N2—C3 | 122.27 (18) | C1i—C7—C6 | 111.41 (16) |
N2—C3—C4 | 111.94 (16) |
Symmetry code: (i) −x, −y+1, −z+1. |
[Ni(C10H18N4O2)]·2H2O | F(000) = 680 |
Mr = 321.03 | Dx = 1.565 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 20.861 (3) Å | Cell parameters from 1275 reflections |
b = 7.3385 (10) Å | θ = 3–20° |
c = 9.6130 (13) Å | µ = 1.44 mm−1 |
β = 112.205 (2)° | T = 180 K |
V = 1362.5 (3) Å3 | Plate, red |
Z = 4 | 0.40 × 0.15 × 0.04 mm |
Siemens SMART CCD area-detector diffractometer | 1193 independent reflections |
Radiation source: normal-focus sealed tube | 799 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 8.192 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
ω scans | h = −24→24 |
Absorption correction: ψ-scan (SADABS; Sheldrick, 1996) | k = −6→8 |
Tmin = 0.67, Tmax = 0.96 | l = −11→11 |
3255 measured reflections |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.079P)2] where P = (Fo2 + 2Fc2)/3 |
1193 reflections | (Δ/σ)max = 0.025 |
91 parameters | Δρmax = 0.90 e Å−3 |
0 restraints | Δρmin = −0.53 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 1/4 | 1/4 | 0 | 0.0239 (4) | |
O1 | 0.1331 (2) | 0.6724 (6) | 0.0596 (5) | 0.0422 (12) | |
C1 | 0.2651 (3) | 0.5716 (9) | 0.1724 (7) | 0.0339 (16) | |
H1A | 0.2564 | 0.7034 | 0.1518 | 0.041* | |
H1B | 0.2633 | 0.5444 | 0.2717 | 0.041* | |
N2 | 0.2128 (2) | 0.4618 (7) | 0.0531 (5) | 0.0296 (12) | |
C3 | 0.1502 (3) | 0.5278 (10) | 0.0070 (7) | 0.0350 (16) | |
C4 | 0.0935 (3) | 0.4286 (10) | −0.1181 (8) | 0.0477 (19) | |
H4A | 0.0490 | 0.4529 | −0.1069 | 0.057* | |
H4B | 0.0903 | 0.4824 | −0.2150 | 0.057* | |
C5 | 0.1009 (3) | 0.2303 (10) | −0.1273 (8) | 0.0399 (17) | |
H5A | 0.1000 | 0.1740 | −0.0344 | 0.048* | |
H5B | 0.0606 | 0.1830 | −0.2127 | 0.048* | |
N6 | 0.1635 (3) | 0.1744 (8) | −0.1461 (6) | 0.0318 (13) | |
H6A | 0.169 (3) | 0.230 (9) | −0.220 (7) | 0.038* | |
C7 | 0.1670 (3) | −0.0209 (9) | −0.1706 (7) | 0.0397 (17) | |
H7A | 0.1302 | −0.0552 | −0.2674 | 0.048* | |
H7B | 0.1589 | −0.0886 | −0.0896 | 0.048* | |
O2 | 0.0083 (2) | 0.8499 (6) | −0.0915 (5) | 0.0465 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0207 (6) | 0.0223 (6) | 0.0244 (6) | 0.0015 (6) | 0.0037 (4) | −0.0033 (6) |
O1 | 0.038 (3) | 0.031 (3) | 0.047 (3) | 0.014 (2) | 0.005 (2) | −0.009 (2) |
C1 | 0.024 (3) | 0.026 (4) | 0.044 (4) | 0.005 (3) | 0.004 (3) | −0.005 (3) |
N2 | 0.025 (3) | 0.028 (3) | 0.031 (3) | 0.000 (2) | 0.005 (2) | −0.002 (2) |
C3 | 0.030 (4) | 0.040 (4) | 0.033 (3) | 0.001 (3) | 0.010 (3) | 0.001 (3) |
C4 | 0.033 (4) | 0.051 (5) | 0.050 (4) | 0.012 (4) | 0.005 (3) | −0.011 (4) |
C5 | 0.023 (3) | 0.036 (5) | 0.058 (4) | −0.003 (3) | 0.011 (3) | −0.011 (4) |
N6 | 0.026 (3) | 0.032 (3) | 0.033 (3) | 0.002 (2) | 0.006 (2) | −0.005 (3) |
C7 | 0.032 (4) | 0.029 (4) | 0.050 (4) | −0.007 (3) | 0.006 (3) | −0.010 (3) |
O2 | 0.044 (3) | 0.034 (3) | 0.053 (3) | 0.012 (2) | 0.009 (2) | 0.000 (2) |
Ni1—N2i | 1.892 (5) | N2—C3 | 1.303 (7) |
Ni1—N2 | 1.892 (5) | C3—C4 | 1.517 (9) |
Ni1—N6i | 1.902 (5) | C4—C5 | 1.470 (9) |
Ni1—N6 | 1.902 (5) | C5—N6 | 1.444 (8) |
O1—C3 | 1.282 (7) | N6—C7 | 1.458 (8) |
C1—C7i | 1.470 (8) | C7—C1i | 1.470 (8) |
C1—N2 | 1.487 (7) | N6—H6A | 0.864 (10) |
N2i—Ni1—N2 | 180 | O1—C3—N2 | 124.4 (6) |
N2i—Ni1—N6i | 93.9 (2) | O1—C3—C4 | 117.4 (5) |
N2—Ni1—N6i | 86.1 (2) | N2—C3—C4 | 118.2 (6) |
N2i—Ni1—N6 | 86.1 (2) | C5—C4—C3 | 117.0 (6) |
N2—Ni1—N6 | 93.9 (2) | N6—C5—C4 | 114.2 (6) |
N6i—Ni1—N6 | 180 | C5—N6—C7 | 113.7 (5) |
C7i—C1—N2 | 106.4 (5) | C5—N6—Ni1 | 118.3 (4) |
C3—N2—C1 | 114.2 (5) | C7—N6—Ni1 | 108.3 (4) |
C3—N2—Ni1 | 132.4 (4) | N6—C7—C1i | 110.9 (5) |
C1—N2—Ni1 | 113.4 (3) |
Symmetry code: (i) −x+1/2, −y+1/2, −z. |