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A new compound, [Ni(pic)2{CO(NH2)2}2]·2[CO(NH2)2]·H2O (Hpic is picolinic acid) or [Ni(C6H4NO2)2(CH4N2O)2]·2CH4N2O·H2O, has been synthesized and structurally characterized by single-crystal X-ray diffraction analysis. The structure shows that the Ni atom has an octahedral environment in which it is coordinated by two N and two O atoms of two picolinate ligands and two O atoms of two urea mol­ecules. The Ni atom lies at an inversion center, with Ni—N = 2.0531 (18) Å, Ni—O(pic) = 2.0349 (15) Å and Ni—O(urea) = 2.1255 (15) Å. Both urea solvent mol­ecules lie on mirror planes and have approximate C2v symmetry, and the water mol­ecule has exact mirror symmetry. π–π stacking and hydrogen-bonding interactions result in a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804008487/wn6231sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804008487/wn6231Isup2.hkl
Contains datablock I

CCDC reference: 239054

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in solvent or counterion
  • R factor = 0.042
  • wR factor = 0.109
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.583 0.803 Tmin' and Tmax expected: 0.685 0.803 RR' = 0.851 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.83 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... C21 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 18.00 Perc. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C14 H16 N6 Ni O6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C H4 N2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 3 C H4 N2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 4 H2 O
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART and SAINT (Siemens, 1994); data reduction: XPREP in SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(I) top
Crystal data top
[Ni(C6H4NO2)2(CH4N2O)2]·2CH4N2O·H2ODx = 1.554 Mg m3
Mr = 561.18Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PnmaCell parameters from 3906 reflections
a = 7.4562 (5) Åθ = 3.0–25.1°
b = 20.3619 (14) ŵ = 0.88 mm1
c = 15.8017 (10) ÅT = 293 K
V = 2399.1 (3) Å3Prism, pale blue
Z = 40.42 × 0.38 × 0.25 mm
F(000) = 1168
Data collection top
Siemens SMART CCD
diffractometer
2167 independent reflections
Radiation source: fine-focus sealed tube1564 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 25.1°, θmin = 3.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 78
Tmin = 0.583, Tmax = 0.803k = 1824
7104 measured reflectionsl = 818
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0391P)2 + 4.0512P]
where P = (Fo2 + 2Fc2)/3
2167 reflections(Δ/σ)max < 0.001
187 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.27 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*/UeqOcc. (<1)
Ni10.50000.50000.50000.03140 (10)
N21.0168 (3)0.40515 (11)0.49250 (14)0.0509 (6)
H2A1.08400.43910.48600.061*
H2B1.06360.36650.49320.061*
O10.7718 (2)0.46854 (7)0.50045 (10)0.0373 (4)
N10.7445 (3)0.35788 (10)0.51424 (15)0.0565 (7)
H1A0.63060.36060.52220.068*
H1B0.79630.32020.51450.068*
C10.8408 (3)0.41231 (11)0.50144 (14)0.0362 (6)
O110.6232 (3)0.64791 (9)0.65844 (12)0.0655 (6)
O120.5905 (2)0.58854 (7)0.54174 (9)0.0359 (4)
N110.4842 (2)0.48409 (9)0.62809 (12)0.0367 (5)
C110.5876 (3)0.59598 (11)0.62147 (15)0.0407 (6)
C120.5330 (3)0.53724 (12)0.67318 (14)0.0379 (6)
C130.5346 (4)0.53706 (13)0.76025 (16)0.0520 (7)
H13A0.56750.57450.79010.062*
C140.4865 (4)0.48050 (16)0.80267 (18)0.0626 (9)
H14A0.48810.47930.86150.075*
C150.4364 (4)0.42598 (14)0.75717 (17)0.0588 (8)
H15A0.40350.38750.78470.071*
C160.4356 (4)0.42939 (12)0.66985 (16)0.0474 (7)
H16A0.40040.39270.63900.057*
O210.7111 (4)0.75000.23655 (18)0.0736 (10)
N210.8593 (5)0.75000.3613 (2)0.0756 (12)
H21A0.96190.75000.33650.091*
H21B0.85350.75000.41570.091*
N220.5522 (5)0.75000.3572 (2)0.0637 (11)
H22A0.45200.75000.33030.076*
H22B0.55290.75000.41170.076*
C210.7064 (6)0.75000.3147 (3)0.0553 (11)
O310.0379 (3)0.75000.55338 (14)0.0467 (7)
N310.2038 (8)0.7150 (3)0.6644 (3)0.0860 (19)0.50
H31A0.27390.69320.63170.103*0.50
H31B0.22160.71500.71820.103*0.50
N320.0456 (7)0.7826 (2)0.6841 (3)0.0661 (15)0.50
H32A0.13580.80420.66470.079*0.50
H32B0.02520.78190.73770.079*0.50
C310.0634 (6)0.75000.6308 (3)0.0587 (12)
O1W0.5744 (5)0.75000.53977 (19)0.0709 (9)
H1C0.607 (3)0.7114 (6)0.5698 (12)0.085*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.03151 (19)0.02755 (18)0.03513 (19)0.00091 (18)0.00072 (19)0.00035 (17)
N20.0328 (10)0.0386 (10)0.0813 (15)0.0044 (9)0.0054 (11)0.0028 (11)
O10.0303 (7)0.0293 (7)0.0523 (9)0.0006 (7)0.0010 (8)0.0040 (8)
N10.0371 (11)0.0304 (10)0.1019 (18)0.0009 (9)0.0025 (12)0.0052 (12)
C10.0380 (12)0.0307 (11)0.0399 (12)0.0020 (10)0.0008 (11)0.0054 (11)
O110.1033 (16)0.0403 (9)0.0529 (11)0.0157 (10)0.0007 (11)0.0120 (9)
O120.0368 (8)0.0312 (8)0.0397 (8)0.0038 (7)0.0004 (7)0.0008 (7)
N110.0358 (10)0.0363 (10)0.0380 (10)0.0001 (9)0.0047 (9)0.0004 (8)
C110.0393 (13)0.0353 (12)0.0475 (13)0.0026 (11)0.0011 (12)0.0036 (11)
C120.0355 (13)0.0391 (12)0.0389 (12)0.0052 (10)0.0022 (10)0.0007 (11)
C130.0617 (17)0.0529 (15)0.0414 (13)0.0015 (13)0.0012 (13)0.0064 (13)
C140.074 (2)0.0736 (19)0.0405 (14)0.0060 (17)0.0064 (14)0.0057 (14)
C150.0668 (17)0.0586 (15)0.0509 (15)0.0018 (15)0.0099 (14)0.0196 (14)
C160.0510 (15)0.0381 (13)0.0531 (14)0.0039 (12)0.0023 (13)0.0044 (12)
O210.0576 (18)0.108 (2)0.0550 (17)0.0000.0003 (15)0.000
N210.058 (2)0.105 (3)0.064 (2)0.0000.0058 (19)0.000
N220.061 (2)0.076 (2)0.0540 (19)0.0000.0041 (17)0.000
C210.058 (2)0.047 (2)0.061 (2)0.0000.000 (2)0.000
O310.0556 (16)0.0454 (13)0.0393 (13)0.0000.0017 (12)0.000
N310.085 (3)0.122 (4)0.051 (3)0.038 (3)0.012 (3)0.010 (3)
N320.065 (3)0.087 (3)0.047 (2)0.013 (3)0.002 (2)0.017 (2)
C310.043 (2)0.083 (3)0.051 (2)0.0000.0008 (19)0.000
O1W0.096 (2)0.0523 (16)0.0643 (17)0.0000.0219 (17)0.000
Geometric parameters (Å, º) top
Ni1—O12i2.0349 (15)C14—H14A0.9300
Ni1—O122.0349 (15)C15—C161.382 (4)
Ni1—N112.0531 (18)C15—H15A0.9300
Ni1—N11i2.0531 (18)C16—H16A0.9300
Ni1—O12.1255 (15)O21—C211.235 (5)
Ni1—O1i2.1255 (15)N21—C211.357 (5)
N2—C11.328 (3)N21—H21A0.8600
N2—H2A0.8600N21—H21B0.8600
N2—H2B0.8600N22—C211.332 (5)
O1—C11.255 (3)N22—H22A0.8600
N1—C11.336 (3)N22—H22B0.8600
N1—H1A0.8600O31—C311.238 (5)
N1—H1B0.8600N31—C311.373 (6)
O11—C111.237 (3)N31—N32ii1.886 (7)
O12—C111.269 (3)N31—H31A0.8600
N11—C161.344 (3)N31—H31B0.8600
N11—C121.346 (3)N32—C311.346 (6)
C11—C121.504 (3)N32—N31ii1.886 (7)
C12—C131.376 (3)N32—H32A0.8600
C13—C141.380 (4)N32—H32B0.8600
C13—H13A0.9300O1W—H1C0.950 (9)
C14—C151.374 (4)
O12i—Ni1—O12180C12—C13—H13A120.5
O12i—Ni1—N1199.24 (7)C14—C13—H13A120.5
O12—Ni1—N1180.76 (7)C15—C14—C13119.4 (2)
O12i—Ni1—N11i80.76 (7)C15—C14—H14A120.3
O12—Ni1—N11i99.24 (7)C13—C14—H14A120.3
N11—Ni1—N11i180C14—C15—C16118.9 (3)
O12i—Ni1—O192.88 (6)C14—C15—H15A120.6
O12—Ni1—O187.12 (6)C16—C15—H15A120.6
N11—Ni1—O190.22 (7)N11—C16—C15122.1 (2)
N11i—Ni1—O189.78 (7)N11—C16—H16A119.0
O12i—Ni1—O1i87.12 (6)C15—C16—H16A119.0
O12—Ni1—O1i92.88 (6)C21—N21—H21A120.0
N11—Ni1—O1i89.78 (7)C21—N21—H21B120.0
N11i—Ni1—O1i90.22 (7)H21A—N21—H21B120.0
O1—Ni1—O1i180C21—N22—H22A120.0
C1—N2—H2A120.0C21—N22—H22B120.0
C1—N2—H2B120.0H22A—N22—H22B120.0
H2A—N2—H2B120.0O21—C21—N22122.0 (4)
C1—O1—Ni1131.75 (14)O21—C21—N21121.2 (4)
C1—N1—H1A120.0N22—C21—N21116.8 (4)
C1—N1—H1B120.0C31—N31—N32ii45.5 (3)
H1A—N1—H1B120.0C31—N31—H31A120.0
O1—C1—N2120.3 (2)N32ii—N31—H31A135.4
O1—C1—N1122.5 (2)C31—N31—H31B120.0
N2—C1—N1117.1 (2)N32ii—N31—H31B89.4
C11—O12—Ni1114.95 (14)H31A—N31—H31B120.0
C16—N11—C12118.6 (2)C31—N32—N31ii46.7 (3)
C16—N11—Ni1129.06 (16)C31—N32—H32A120.0
C12—N11—Ni1112.30 (15)N31ii—N32—H32A134.3
O11—C11—O12124.6 (2)C31—N32—H32B120.0
O11—C11—C12118.8 (2)N31ii—N32—H32B89.3
O12—C11—C12116.7 (2)H32A—N32—H32B120.0
N11—C12—C13122.0 (2)O31—C31—N32121.7 (4)
N11—C12—C11115.14 (19)O31—C31—N31119.9 (4)
C13—C12—C11122.9 (2)N32—C31—N31118.3 (4)
C12—C13—C14119.1 (2)
Symmetry codes: (i) x+1, y+1, z1; (ii) x, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O12i0.862.192.866 (3)135
N1—H1B···O31i0.862.172.932 (3)147
N2—H2A···O1iii0.862.183.019 (3)166
N2—H2A···O12iii0.862.532.980 (3)114
N21—H21A···O21iv0.862.193.045 (5)175
N22—H22B···O1W0.862.032.889 (5)176
N22—H22A···O21v0.862.082.944 (5)179
N31—H31B···N32vi0.862.323.036 (7)141
N32—H32A···O11vii0.862.052.874 (5)161
O1W—H1C···O110.95 (1)1.91 (1)2.823 (3)161 (2)
Symmetry codes: (i) x+1, y+1, z1; (iii) x+2, y+1, z1; (iv) x+1/2, y, z1/2; (v) x1/2, y, z1/2; (vi) x+1/2, y+3/2, z3/2; (vii) x1, y+3/2, z.
 

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