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In the mol­ecule of the title compound, [Ni(C12H8N2)2(C4H8N2O2)](NO3)2·2H2O, the Ni atom has a distorted octa­hedral coordination formed by six N atoms from one dimethyl­glyoxime and two 1,10-phenanthroline ligands. In the crystal structure, mol­ecules are linked into a three-dimensional framework by O—H...O hydrogen bonds and π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004102/hk2193sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004102/hk2193Isup2.hkl
Contains datablock I

CCDC reference: 1302176

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.049
  • wR factor = 0.153
  • Data-to-parameter ratio = 15.8

checkCIF/PLATON results

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Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O2 - H2 ... ? PLAT420_ALERT_2_B D-H Without Acceptor O9 - H9B ... ? PLAT420_ALERT_2_B D-H Without Acceptor O10 - H10A ... ? PLAT420_ALERT_2_B D-H Without Acceptor O10 - H10B ... ?
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N7 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N8
0 ALERT level A = In general: serious problem 4 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

(Dimethylglyoxime-κ2N,N')bis(1,10-phenanthroline-κ2N,N')nickel(II) dinitrate dihydrate top
Crystal data top
[Ni(C12H8N2)2(C4H8N2O2)](NO3)2·2H2OF(000) = 1440
Mr = 695.27Dx = 1.512 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5768 reflections
a = 13.8759 (19) Åθ = 2.3–25.0°
b = 12.045 (5) ŵ = 0.71 mm1
c = 18.3778 (18) ÅT = 273 K
β = 96.145 (1)°Prism, green
V = 3053.9 (14) Å30.30 × 0.23 × 0.18 mm
Z = 4
Data collection top
Bruker APEX-II area-detector
diffractometer
7021 independent reflections
Radiation source: fine-focus sealed tube3780 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 27.9°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1718
Tmin = 0.817, Tmax = 0.883k = 1515
22071 measured reflectionsl = 2324
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 0.93 w = 1/[σ2(Fo2) + (0.1P)2 + 0.002P]
where P = (Fo2 + 2Fc2)/3
7021 reflections(Δ/σ)max = 0.006
444 parametersΔρmax = 0.76 e Å3
12 restraintsΔρmin = 0.53 e Å3
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
Ni10.77584 (3)0.75555 (4)0.03824 (3)0.04167 (18)
O10.7958 (2)0.9962 (2)0.04781 (16)0.0530 (7)
H10.80660.99860.00480.080*
O20.8358 (2)0.6032 (2)0.14817 (18)0.0601 (8)
H20.79730.59460.17860.090*
O30.7740 (3)0.1306 (3)0.9097 (2)0.0872 (11)
O40.8930 (2)0.0151 (3)0.92837 (19)0.0693 (9)
O50.8892 (3)0.1344 (4)0.8440 (3)0.1216 (17)
O60.7395 (6)0.8812 (7)0.2864 (4)0.196 (3)
O70.6163 (6)0.8867 (6)0.3337 (4)0.197 (3)
O80.6380 (8)1.0092 (6)0.2618 (6)0.224 (11)
O90.5637 (12)0.4288 (12)0.1497 (10)0.320 (12)
O100.7008 (17)0.3302 (17)0.1996 (10)0.350 (16)
N10.6532 (2)0.7799 (2)0.07677 (19)0.0415 (8)
N20.7070 (2)0.8185 (2)0.05332 (17)0.0387 (8)
N30.7383 (2)0.6058 (2)0.00400 (18)0.0430 (8)
N40.8936 (2)0.7247 (2)0.00735 (17)0.0373 (8)
N50.8376 (2)0.7051 (3)0.12998 (18)0.0420 (8)
N60.8223 (2)0.8935 (2)0.07673 (18)0.0398 (8)
N70.8517 (3)0.0919 (3)0.8924 (2)0.0617 (10)
N80.6648 (5)0.9338 (9)0.2883 (5)0.149 (4)
C10.6306 (3)0.7615 (3)0.1434 (2)0.0519 (11)
H1A0.67800.73500.17880.062*
C20.5366 (3)0.7807 (4)0.1627 (3)0.0655 (13)
H2A0.52290.76860.21050.079*
C30.4658 (3)0.8170 (4)0.1113 (3)0.0598 (13)
H30.40320.82770.12370.072*
C40.4867 (3)0.8381 (3)0.0408 (3)0.0487 (11)
C50.4205 (3)0.8798 (4)0.0162 (3)0.0625 (13)
H50.35670.89250.00750.075*
C60.4478 (3)0.9020 (4)0.0838 (3)0.0665 (14)
H60.40230.92970.12010.080*
C70.5458 (3)0.8834 (3)0.1002 (3)0.0543 (12)
C80.5797 (4)0.9063 (4)0.1661 (3)0.0631 (13)
H80.53820.93510.20460.076*
C90.6762 (4)0.8864 (4)0.1751 (3)0.0646 (13)
H90.70020.90350.21910.078*
C100.7373 (3)0.8401 (3)0.1170 (2)0.0486 (11)
H100.80130.82430.12390.058*
C110.6126 (3)0.8400 (3)0.0440 (2)0.0427 (10)
C120.5834 (3)0.8182 (3)0.0254 (2)0.0400 (9)
C130.6605 (3)0.5465 (4)0.0145 (3)0.0593 (12)
H130.61430.57640.04200.071*
C140.6464 (3)0.4403 (4)0.0151 (3)0.0722 (15)
H140.59080.40070.00750.087*
C150.7132 (4)0.3944 (4)0.0548 (3)0.0692 (14)
H150.70370.32350.07430.083*
C160.7965 (3)0.4544 (3)0.0660 (2)0.0478 (11)
C170.8728 (4)0.4154 (4)0.1062 (2)0.0558 (12)
H170.86650.34670.12930.067*
C180.9523 (3)0.4751 (4)0.1112 (2)0.0552 (12)
H181.00090.44650.13680.066*
C190.9649 (3)0.5827 (3)0.0780 (2)0.0437 (10)
C201.0468 (3)0.6507 (4)0.0801 (2)0.0540 (12)
H201.09870.62710.10430.065*
C211.0494 (3)0.7509 (4)0.0466 (2)0.0521 (11)
H211.10340.79620.04770.063*
C220.9719 (3)0.7866 (3)0.0105 (2)0.0453 (10)
H220.97520.85580.01210.054*
C230.8906 (3)0.6240 (3)0.0408 (2)0.0395 (9)
C240.8065 (3)0.5597 (3)0.0349 (2)0.0397 (9)
C250.8796 (3)0.7813 (3)0.1717 (2)0.0432 (10)
C260.8676 (3)0.8916 (3)0.1415 (2)0.0461 (10)
C270.9045 (3)0.9928 (4)0.1828 (3)0.0674 (13)
H27A0.91271.05190.14890.101*
H27B0.96570.97640.21020.101*
H27C0.85881.01510.21570.101*
C280.9315 (3)0.7561 (4)0.2443 (2)0.0662 (13)
H28A0.91890.68060.25720.099*
H28B0.90950.80520.28020.099*
H28C0.99990.76600.24270.099*
H9A0.520 (4)0.403 (3)0.118 (3)0.526 (16)*
H10B0.731 (3)0.304 (3)0.167 (2)0.553 (13)*
H9B0.5620 (19)0.4959 (13)0.1574 (16)0.520 (6)*
H10A0.673 (7)0.281 (4)0.222 (5)0.55 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0380 (3)0.0409 (3)0.0454 (3)0.0023 (2)0.0012 (2)0.0022 (3)
O10.0635 (18)0.0391 (16)0.055 (2)0.0071 (13)0.0016 (16)0.0002 (14)
O20.061 (2)0.055 (2)0.063 (2)0.0017 (15)0.0024 (15)0.0187 (16)
O30.063 (2)0.089 (3)0.111 (3)0.0152 (19)0.018 (2)0.007 (2)
O40.068 (2)0.056 (2)0.083 (3)0.0095 (16)0.0017 (18)0.0150 (18)
O50.114 (3)0.130 (4)0.130 (4)0.029 (3)0.054 (3)0.060 (3)
O60.166 (6)0.243 (8)0.181 (7)0.070 (6)0.028 (6)0.067 (5)
O70.233 (8)0.199 (7)0.155 (7)0.010 (6)0.007 (6)0.028 (5)
O80.547 (19)0.227 (6)0.403 (15)0.071 (7)0.364 (14)0.123 (7)
O90.50 (3)0.64 (3)0.50 (3)0.07 (2)0.39 (2)0.00 (2)
O100.39 (2)0.88 (4)0.36 (2)0.03 (2)0.072 (16)0.35 (3)
N10.0376 (18)0.0393 (18)0.047 (2)0.0030 (14)0.0013 (15)0.0010 (15)
N20.0415 (19)0.0334 (18)0.040 (2)0.0038 (14)0.0020 (15)0.0046 (15)
N30.0383 (18)0.0371 (18)0.053 (2)0.0013 (15)0.0009 (16)0.0012 (16)
N40.0329 (17)0.0334 (18)0.044 (2)0.0032 (13)0.0019 (14)0.0010 (14)
N50.0368 (18)0.0426 (19)0.046 (2)0.0043 (15)0.0023 (15)0.0060 (17)
N60.0384 (18)0.0348 (18)0.045 (2)0.0020 (14)0.0015 (15)0.0011 (15)
N70.055 (3)0.061 (3)0.071 (3)0.007 (2)0.012 (2)0.010 (2)
N80.090 (5)0.244 (12)0.116 (7)0.060 (6)0.020 (5)0.090 (7)
C10.045 (2)0.064 (3)0.048 (3)0.008 (2)0.0055 (19)0.007 (2)
C20.057 (3)0.076 (3)0.066 (3)0.003 (2)0.019 (3)0.003 (3)
C30.040 (3)0.058 (3)0.083 (4)0.000 (2)0.014 (2)0.014 (3)
C40.037 (2)0.037 (2)0.071 (3)0.0010 (17)0.002 (2)0.008 (2)
C50.038 (2)0.057 (3)0.091 (4)0.004 (2)0.004 (3)0.008 (3)
C60.050 (3)0.053 (3)0.090 (4)0.013 (2)0.020 (3)0.009 (3)
C70.056 (3)0.043 (2)0.059 (3)0.002 (2)0.015 (2)0.005 (2)
C80.075 (3)0.052 (3)0.057 (3)0.011 (2)0.014 (3)0.001 (2)
C90.099 (4)0.046 (3)0.046 (3)0.002 (3)0.003 (3)0.003 (2)
C100.061 (3)0.045 (2)0.039 (3)0.002 (2)0.001 (2)0.004 (2)
C110.045 (2)0.030 (2)0.050 (3)0.0016 (17)0.0081 (19)0.0031 (19)
C120.039 (2)0.031 (2)0.048 (3)0.0007 (16)0.0006 (18)0.0039 (19)
C130.046 (3)0.048 (3)0.084 (4)0.004 (2)0.008 (2)0.002 (2)
C140.059 (3)0.048 (3)0.109 (5)0.015 (2)0.007 (3)0.011 (3)
C150.074 (3)0.039 (3)0.091 (4)0.008 (2)0.007 (3)0.013 (3)
C160.056 (3)0.037 (2)0.048 (3)0.006 (2)0.008 (2)0.002 (2)
C170.076 (3)0.044 (3)0.045 (3)0.013 (2)0.006 (2)0.006 (2)
C180.072 (3)0.055 (3)0.038 (3)0.028 (2)0.003 (2)0.004 (2)
C190.048 (2)0.049 (2)0.033 (2)0.012 (2)0.0007 (18)0.0037 (19)
C200.046 (3)0.071 (3)0.045 (3)0.013 (2)0.009 (2)0.005 (2)
C210.041 (2)0.061 (3)0.054 (3)0.003 (2)0.0046 (19)0.001 (2)
C220.042 (2)0.042 (2)0.051 (3)0.0025 (18)0.0004 (19)0.0018 (19)
C230.041 (2)0.041 (2)0.035 (2)0.0062 (18)0.0043 (17)0.0021 (18)
C240.045 (2)0.036 (2)0.036 (2)0.0068 (18)0.0021 (18)0.0007 (18)
C250.040 (2)0.052 (2)0.037 (2)0.0021 (18)0.0004 (18)0.002 (2)
C260.043 (2)0.050 (2)0.045 (3)0.0011 (19)0.003 (2)0.013 (2)
C270.076 (3)0.062 (3)0.063 (3)0.006 (2)0.001 (3)0.020 (3)
C280.065 (3)0.080 (3)0.051 (3)0.004 (2)0.009 (2)0.005 (3)
Geometric parameters (Å, º) top
Ni1—N11.934 (3)C6—C71.441 (6)
Ni1—N21.994 (3)C6—H60.9300
Ni1—N31.963 (3)C7—C81.374 (6)
Ni1—N41.950 (3)C7—C111.412 (6)
Ni1—N51.907 (3)C8—C91.387 (6)
Ni1—N61.892 (3)C8—H80.9300
O1—N61.380 (4)C9—C101.406 (6)
O1—H10.8200C9—H90.9300
O2—N51.273 (4)C10—H100.9300
O2—H20.8200C11—C121.404 (5)
O3—N71.247 (5)C13—C141.396 (6)
O4—N71.241 (5)C13—H130.9300
O5—N71.192 (5)C14—C151.358 (6)
O6—N81.219 (9)C14—H140.9300
O7—N81.261 (8)C15—C161.397 (6)
O8—N81.078 (10)C15—H150.9300
O9—H9A0.85 (5)C16—C241.393 (5)
O9—H9B0.822 (10)C16—C171.433 (6)
O10—H10B0.83 (4)C17—C181.328 (6)
O10—H10A0.84 (8)C17—H170.9300
N1—C11.316 (5)C18—C191.434 (6)
N1—C121.359 (5)C18—H180.9300
N2—C101.311 (5)C19—C231.390 (5)
N2—C111.363 (5)C19—C201.404 (6)
N3—C131.326 (5)C20—C211.355 (6)
N3—C241.364 (5)C20—H200.9300
N4—C221.325 (5)C21—C221.390 (5)
N4—C231.359 (4)C21—H210.9300
N5—C251.295 (5)C22—H220.9300
N6—C261.286 (5)C23—C241.414 (5)
C1—C21.406 (6)C25—C261.442 (5)
C1—H1A0.9300C25—C281.478 (5)
C2—C31.360 (6)C26—C271.497 (5)
C2—H2A0.9300C27—H27A0.9600
C3—C41.381 (6)C27—H27B0.9600
C3—H30.9300C27—H27C0.9600
C4—C51.410 (6)C28—H28A0.9600
C4—C121.421 (5)C28—H28B0.9600
C5—C61.363 (7)C28—H28C0.9600
C5—H50.9300
N1—Ni1—N283.70 (13)C8—C9—C10119.4 (5)
N1—Ni1—N392.48 (13)C8—C9—H9120.3
N1—Ni1—N4175.30 (13)C10—C9—H9120.3
N1—Ni1—N593.12 (13)N2—C10—C9122.1 (4)
N1—Ni1—N690.47 (13)N2—C10—H10119.0
N2—Ni1—N389.55 (12)C9—C10—H10119.0
N2—Ni1—N493.31 (12)N2—C11—C12116.9 (3)
N2—Ni1—N5175.37 (13)N2—C11—C7122.9 (4)
N2—Ni1—N695.44 (13)C12—C11—C7120.2 (4)
N3—Ni1—N483.86 (13)N1—C12—C11116.2 (3)
N3—Ni1—N593.96 (14)N1—C12—C4122.5 (4)
N3—Ni1—N6174.45 (13)C11—C12—C4121.3 (4)
N4—Ni1—N590.07 (13)N3—C13—C14121.3 (4)
N4—Ni1—N693.43 (12)N3—C13—H13119.4
N5—Ni1—N681.18 (14)C14—C13—H13119.4
N6—O1—H1109.5C15—C14—C13120.5 (4)
N5—O2—H2109.5C15—C14—H14119.8
H9A—O9—H9B117 (3)C13—C14—H14119.8
H10B—O10—H10A113 (3)C14—C15—C16119.5 (4)
C1—N1—C12118.7 (3)C14—C15—H15120.3
C1—N1—Ni1128.5 (3)C16—C15—H15120.3
C12—N1—Ni1112.8 (3)C24—C16—C15117.3 (4)
C10—N2—C11118.6 (3)C24—C16—C17117.5 (4)
C10—N2—Ni1131.1 (3)C15—C16—C17125.1 (4)
C11—N2—Ni1110.3 (3)C18—C17—C16121.6 (4)
C13—N3—C24118.7 (4)C18—C17—H17119.2
C13—N3—Ni1129.8 (3)C16—C17—H17119.2
C24—N3—Ni1111.5 (2)C17—C18—C19121.6 (4)
C22—N4—C23117.9 (3)C17—C18—H18119.2
C22—N4—Ni1129.9 (3)C19—C18—H18119.2
C23—N4—Ni1112.2 (2)C23—C19—C20116.7 (4)
O2—N5—C25123.3 (4)C23—C19—C18118.0 (4)
O2—N5—Ni1121.3 (3)C20—C19—C18125.3 (4)
C25—N5—Ni1115.4 (3)C21—C20—C19119.3 (4)
C26—N6—O1117.2 (3)C21—C20—H20120.4
C26—N6—Ni1116.3 (3)C19—C20—H20120.4
O1—N6—Ni1125.2 (2)C20—C21—C22120.6 (4)
O5—N7—O4120.3 (4)C20—C21—H21119.7
O5—N7—O3119.3 (4)C22—C21—H21119.7
O4—N7—O3120.3 (4)N4—C22—C21121.8 (4)
O8—N8—O6132.8 (12)N4—C22—H22119.1
O8—N8—O7119.7 (11)C21—C22—H22119.1
O6—N8—O7107.5 (11)N4—C23—C19123.7 (4)
N1—C1—C2121.8 (4)N4—C23—C24116.1 (3)
N1—C1—H1A119.1C19—C23—C24120.2 (4)
C2—C1—H1A119.1N3—C24—C16122.7 (4)
C3—C2—C1119.9 (5)N3—C24—C23116.2 (3)
C3—C2—H2A120.0C16—C24—C23121.0 (4)
C1—C2—H2A120.0N5—C25—C26113.5 (4)
C2—C3—C4120.1 (4)N5—C25—C28122.2 (4)
C2—C3—H3119.9C26—C25—C28124.2 (4)
C4—C3—H3119.9N6—C26—C25113.5 (3)
C3—C4—C5125.3 (4)N6—C26—C27124.1 (4)
C3—C4—C12117.0 (4)C25—C26—C27122.4 (4)
C5—C4—C12117.8 (4)C26—C27—H27A109.5
C6—C5—C4121.7 (4)C26—C27—H27B109.5
C6—C5—H5119.2H27A—C27—H27B109.5
C4—C5—H5119.2C26—C27—H27C109.5
C5—C6—C7121.3 (4)H27A—C27—H27C109.5
C5—C6—H6119.3H27B—C27—H27C109.5
C7—C6—H6119.3C25—C28—H28A109.5
C8—C7—C11117.3 (4)C25—C28—H28B109.5
C8—C7—C6124.9 (4)H28A—C28—H28B109.5
C11—C7—C6117.7 (5)C25—C28—H28C109.5
C7—C8—C9119.7 (4)H28A—C28—H28C109.5
C7—C8—H8120.1H28B—C28—H28C109.5
C9—C8—H8120.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O9—H9A···O7i0.85 (5)2.18 (7)2.599 (18)110 (6)
O1—H1···N7ii0.822.493.250 (5)155
O1—H1···O3ii0.822.372.998 (5)134
O1—H1···O4ii0.821.952.706 (4)153
Symmetry codes: (i) x+1, y1/2, z+1/2; (ii) x, y+1, z1.
 

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