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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m280.
Published online 2010 February 13. doi:  10.1107/S1600536810004691
PMCID: PMC2983735

Diaqua­bis(5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ato-κ2 N 3,O 4)nickel(II) N,N-dimethyl­formamide disolvate

Abstract

In the title complex, [Ni(C8H9N2O4)2(H2O)2]·2C3H7NO, the NiII atom is six-coordinated by two N,O-bidentate 5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ate ligands and two water mol­ecules in a distorted octa­hedral environment. The methyl C and H atoms of the two ligands are disordered over two sets of sites in 0.74 (2):0.26 (2) and 0.57 (8):0.43 (8) ratios. A supra­molecular network is stabilized by intra- and inter­molecular N—H(...)O and O—H(...)O hydrogen bonds involving the ligands, coordinated water mol­ecules and dimethyl­formamide solvent mol­ecules.

Related literature

For the structures of related 2-propyl-1H-imidazole-4,5-dicarboxyl­ate complexes, see: Song et al. (2010 [triangle]); Yan et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m280-scheme1.jpg

Experimental

Crystal data

  • [Ni(C8H9N2O4)2(H2O)2]·2C3H7NO
  • M r = 635.26
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m280-efi1.jpg
  • a = 16.3574 (12) Å
  • b = 9.5246 (7) Å
  • c = 18.7700 (13) Å
  • V = 2924.3 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.73 mm−1
  • T = 273 K
  • 0.31 × 0.24 × 0.18 mm

Data collection

  • Rigaku/MSC Mercury CCD diffractometer
  • Absorption correction: multi-scan (REQAB; Jacobson, 1998 [triangle]) T min = 0.805, T max = 0.880
  • 14413 measured reflections
  • 5064 independent reflections
  • 3663 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.133
  • S = 1.03
  • 5064 reflections
  • 403 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.36 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2344 Friedel pairs
  • Flack parameter: 0.01 (2)

Data collection: CrystalStructure (Rigaku/MSC, 2002 [triangle]); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEPII (Johnson, 1976 [triangle]) and DIAMOND (Brandenburg, 1999 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, 1R. DOI: 10.1107/S1600536810004691/hy2277sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004691/hy2277Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge Guang Dong Ocean University for supporting this work.

supplementary crystallographic information

Comment

2-Propyl-1H-imidazole-4,5-dicarboxylate ligand with efficient N,O-donors has been used to obtain new metal–organic complexes, such as poly[diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ3N3,O4,O5)calcium(II)] (Song et al., 2010) and [diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ2N3,O4)manganese(II)] N,N-dimethylformamide (Yan et al., 2010). In this paper, we report the synthesis and structure of a new nickel(II) complex obtained under hydrothermal conditions.

As illustrated in Fig. 1, the title complex molecule is composed of one NiII ion, two mono-deprotonated 2-propyl-1H-imidazole-4,5-dicarboxylate ligands, two coordinated water molecules and two dimethylformamide solvent molecules. The NiII atom exhibits a slightly distorted octahedral coordination geometry, defined by two N,O-bidentate ligands and two water molecules. In the crystal structure, the complex molecules and dimethylformamide solvent molecules are linked by N—H···O and O—H···O hydrogen bonds (Table 1) into a two-dimensional supramolecular structure parallel to (0 0 1) (Fig. 2). The methyl C and H atoms of the two ligands are disordered over two sites in raios of 0.74 (2):0.26 (2) and 0.57 (8):0.43 (8).

Experimental

A mixture of Ni(CH3CO2)2 (0.5 mmol, 0.06 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.99 g) in 15 ml of dimethylformamide solution was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated at 433 K for 4 d. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Refinement

C- and N-bound H atoms were placed at calculated positions and treated as riding on the parent atoms, with C—H = 0.93 (CH), 0.97 (CH2) and 0.96 (CH3) Å and N—H = 0.86 Å and with Uiso(H) = 1.2(1.5 for methyl)Ueq(C,N). The water H atoms were located in a difference map and refined as riding, with O—H = 0.85 Å and Uiso(H) = 1.5Ueq(O). H atoms of carboxyl groups were located in a difference map, and one H atom (H3) was refined isotropically and the other (H7) was refined as riding with O—H = 0.82 Å and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
Molecular structure of the title compound, showing the 30% probability displacement ellipsoids.
Fig. 2.
A view of the two-dimensional network constructed by N—H···O and O—H···O hydrogen bonding interactions (dashed lines).

Crystal data

[Ni(C8H9N2O4)2(H2O)2]·2C3H7NOF(000) = 1336
Mr = 635.26Dx = 1.443 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 3420 reflections
a = 16.3574 (12) Åθ = 3.3–27.4°
b = 9.5246 (7) ŵ = 0.73 mm1
c = 18.7700 (13) ÅT = 273 K
V = 2924.3 (4) Å3Block, green
Z = 40.31 × 0.24 × 0.18 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer5064 independent reflections
Radiation source: fine-focus sealed tube3663 reflections with I > 2σ(I)
graphiteRint = 0.063
ω scansθmax = 25.2°, θmin = 2.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)h = −15→19
Tmin = 0.805, Tmax = 0.880k = −10→11
14413 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133w = 1/[σ2(Fo2) + (0.0549P)2 + 0.3624P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
5064 reflectionsΔρmax = 0.37 e Å3
403 parametersΔρmin = −0.36 e Å3
1 restraintAbsolute structure: Flack (1983), 2344 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Ni10.10751 (4)0.00168 (7)0.09532 (6)0.03620 (17)
N10.0395 (3)−0.1796 (4)0.0878 (2)0.0372 (10)
N2−0.0320 (3)−0.3724 (4)0.0753 (2)0.0406 (12)
H2−0.0680−0.43030.05940.049*
N30.1752 (3)0.1835 (4)0.1021 (2)0.0365 (9)
N40.2477 (3)0.3758 (4)0.1143 (2)0.0390 (12)
H40.28330.43400.13060.047*
N50.3912 (3)0.7166 (5)0.2536 (3)0.0498 (12)
N60.3277 (3)0.2034 (5)0.9330 (3)0.0501 (12)
O10.1630 (2)−0.1165 (3)0.1768 (2)0.0469 (10)
O20.1603 (3)−0.3285 (4)0.2279 (2)0.0554 (11)
O30.0825 (3)−0.5493 (4)0.2133 (2)0.0573 (11)
O4−0.0164 (3)−0.6333 (4)0.1436 (3)0.0591 (12)
O50.0526 (2)0.1182 (3)0.0127 (2)0.0468 (10)
O60.0577 (3)0.3260 (4)−0.0417 (2)0.0531 (10)
O70.1355 (3)0.5476 (5)−0.0274 (2)0.0598 (12)
H70.11490.4704−0.03450.090*
O80.2317 (3)0.6357 (4)0.0427 (2)0.0569 (11)
O90.3702 (2)0.5395 (4)0.1757 (3)0.0588 (11)
O100.3442 (2)0.0345 (4)1.0158 (3)0.0612 (12)
O1W0.1905 (2)−0.0835 (4)0.0234 (2)0.0487 (10)
H1W0.1925−0.17260.02560.073*
H2W0.2379−0.05130.01450.073*
O2W0.0247 (2)0.0860 (4)0.1677 (2)0.0487 (10)
H3W0.01870.17120.15530.073*
H4W−0.02040.04360.16120.073*
C10.0669 (3)−0.2786 (5)0.1358 (3)0.0350 (12)
C20.0221 (3)−0.3993 (5)0.1284 (3)0.0342 (12)
C3−0.0202 (3)−0.2402 (5)0.0517 (3)0.0390 (13)
C40.1346 (4)−0.2387 (6)0.1836 (3)0.0416 (13)
C50.0282 (4)−0.5373 (5)0.1632 (3)0.0469 (14)
C6−0.0674 (4)−0.1725 (6)−0.0067 (3)0.0556 (16)
H6A−0.0729−0.07310.00350.067*
H6B−0.1218−0.2126−0.00810.067*
C7−0.0265 (6)−0.1908 (10)−0.0809 (4)0.097 (3)
H7A−0.0490−0.1214−0.11330.116*0.744 (18)
H7B0.0316−0.1722−0.07630.116*0.744 (18)
H7'A0.0113−0.1125−0.08430.116*0.256 (18)
H7'B0.0076−0.2734−0.07530.116*0.256 (18)
C8−0.0374 (9)−0.3302 (15)−0.1122 (7)0.107 (5)0.744 (18)
H8A−0.0056−0.3974−0.08590.160*0.744 (18)
H8B−0.0196−0.3289−0.16090.160*0.744 (18)
H8C−0.0941−0.3558−0.11020.160*0.744 (18)
C8'−0.064 (3)−0.209 (4)−0.154 (2)0.112 (17)0.256 (18)
H8'1−0.0230−0.2402−0.18670.168*0.256 (18)
H8'2−0.0862−0.1212−0.16970.168*0.256 (18)
H8'3−0.1070−0.2778−0.15140.168*0.256 (18)
C90.1496 (3)0.2789 (5)0.0522 (3)0.0341 (12)
C100.1940 (3)0.4013 (5)0.0583 (3)0.0370 (12)
C110.2348 (3)0.2449 (5)0.1388 (3)0.0405 (13)
C120.0820 (4)0.2391 (5)0.0046 (3)0.0397 (12)
C130.1883 (4)0.5381 (5)0.0228 (3)0.0444 (13)
C140.2779 (4)0.1856 (6)0.2005 (3)0.0566 (17)
H14A0.33640.19090.19260.068*
H14B0.26330.08740.20570.068*
C150.2557 (7)0.2659 (11)0.2700 (5)0.108 (3)
H15A0.25230.36570.26020.130*0.43 (8)
H15B0.20290.23480.28720.130*0.43 (8)
H15C0.29220.34590.27350.130*0.57 (8)
H15D0.20060.30240.26540.130*0.57 (8)
C160.320 (4)0.239 (7)0.326 (2)0.110 (14)0.43 (8)
H16A0.31890.14230.34020.165*0.43 (8)
H16B0.30940.29720.36720.165*0.43 (8)
H16C0.37320.26160.30750.165*0.43 (8)
C16'0.280 (3)0.190 (4)0.3375 (17)0.109 (10)0.57 (8)
H16D0.33030.13990.32950.163*0.57 (8)
H16E0.23810.12590.35100.163*0.57 (8)
H16F0.28850.25770.37500.163*0.57 (8)
C170.3560 (4)0.6586 (6)0.1975 (3)0.0492 (15)
H170.31770.71180.17280.059*
C180.3694 (6)0.8590 (7)0.2739 (4)0.084 (3)
H18A0.33380.89850.23860.125*
H18B0.41810.91500.27740.125*
H18C0.34210.85770.31920.125*
C190.4482 (5)0.6426 (9)0.2966 (4)0.080 (2)
H19A0.46470.70080.33580.120*
H19B0.49520.61830.26850.120*
H19C0.42320.55850.31450.120*
C200.3618 (4)0.1489 (6)0.9896 (3)0.0545 (16)
H200.40260.20091.01190.065*
C210.3507 (6)0.3432 (7)0.9072 (4)0.083 (3)
H21A0.38840.38540.94010.125*
H21B0.30270.40070.90340.125*
H21C0.37610.33490.86130.125*
C220.2656 (5)0.1276 (8)0.8942 (4)0.076 (2)
H22A0.26940.02940.90520.113*
H22B0.27340.14120.84400.113*
H22C0.21260.16180.90770.113*
H10.115 (4)−0.456 (7)0.222 (3)0.050 (16)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.0388 (3)0.0225 (3)0.0473 (3)−0.0047 (2)−0.0047 (3)0.0025 (2)
N10.036 (2)0.032 (2)0.044 (3)−0.0005 (18)−0.006 (2)0.005 (2)
N20.040 (3)0.027 (2)0.055 (3)−0.007 (2)−0.001 (2)−0.0057 (19)
N30.039 (2)0.0246 (19)0.046 (2)−0.0044 (18)−0.004 (2)−0.001 (2)
N40.040 (3)0.030 (2)0.048 (3)−0.010 (2)0.002 (2)−0.0043 (19)
N50.050 (3)0.040 (3)0.059 (3)−0.004 (2)0.007 (3)−0.009 (2)
N60.051 (3)0.043 (3)0.057 (3)−0.003 (2)0.001 (3)0.004 (2)
O10.052 (2)0.030 (2)0.058 (2)−0.0088 (18)−0.014 (2)0.0028 (19)
O20.065 (3)0.045 (2)0.056 (2)0.000 (2)−0.020 (2)0.0156 (19)
O30.067 (3)0.039 (2)0.066 (3)−0.002 (2)−0.004 (3)0.016 (2)
O40.054 (3)0.028 (2)0.095 (4)−0.0086 (19)0.011 (2)0.006 (2)
O50.049 (2)0.033 (2)0.059 (2)−0.0060 (17)−0.013 (2)0.0011 (19)
O60.062 (3)0.046 (2)0.051 (2)−0.001 (2)−0.012 (2)0.0124 (19)
O70.068 (3)0.043 (2)0.069 (3)−0.002 (2)−0.002 (3)0.020 (2)
O80.056 (3)0.028 (2)0.086 (3)−0.0050 (19)0.002 (2)0.008 (2)
O90.043 (2)0.053 (3)0.080 (3)−0.0041 (19)−0.005 (2)−0.016 (2)
O100.048 (3)0.048 (2)0.088 (3)−0.0001 (19)−0.007 (2)0.023 (2)
O1W0.049 (2)0.032 (2)0.066 (3)−0.0044 (18)0.006 (2)−0.0012 (18)
O2W0.053 (3)0.0281 (19)0.065 (3)−0.0043 (18)0.003 (2)−0.0001 (18)
C10.037 (3)0.029 (3)0.039 (3)−0.002 (2)−0.001 (3)0.006 (2)
C20.033 (3)0.027 (2)0.043 (3)0.001 (2)0.009 (2)0.002 (2)
C30.041 (3)0.027 (3)0.049 (3)0.000 (2)−0.003 (3)0.001 (2)
C40.042 (4)0.036 (3)0.046 (3)0.000 (3)−0.005 (3)0.003 (3)
C50.054 (4)0.029 (3)0.058 (4)0.001 (3)0.013 (3)0.006 (3)
C60.057 (4)0.048 (3)0.062 (4)−0.010 (3)−0.014 (3)0.007 (3)
C70.111 (7)0.105 (7)0.074 (6)0.009 (5)−0.011 (5)0.011 (5)
C80.118 (11)0.112 (11)0.090 (9)0.029 (8)−0.025 (8)−0.022 (8)
C8'0.14 (4)0.10 (3)0.10 (3)0.01 (3)−0.03 (3)0.00 (2)
C90.035 (3)0.026 (3)0.041 (3)−0.002 (2)0.004 (2)−0.003 (2)
C100.039 (3)0.027 (3)0.044 (3)0.000 (2)0.002 (3)−0.002 (2)
C110.042 (4)0.033 (3)0.046 (3)−0.002 (2)−0.004 (3)−0.004 (3)
C120.043 (3)0.031 (3)0.045 (3)0.004 (3)0.001 (3)−0.002 (3)
C130.040 (3)0.033 (3)0.061 (4)0.002 (3)0.010 (3)0.004 (3)
C140.065 (4)0.042 (3)0.063 (4)−0.009 (3)−0.016 (3)0.010 (3)
C150.124 (8)0.124 (8)0.077 (6)0.011 (7)−0.019 (6)0.022 (6)
C160.13 (3)0.12 (3)0.081 (18)0.00 (2)−0.03 (2)0.026 (18)
C16'0.13 (3)0.11 (2)0.081 (14)−0.005 (15)−0.005 (16)0.001 (13)
C170.041 (3)0.041 (3)0.066 (4)0.005 (3)0.001 (3)−0.001 (3)
C180.119 (7)0.047 (4)0.084 (5)0.002 (4)0.009 (5)−0.012 (4)
C190.071 (5)0.092 (6)0.078 (5)0.013 (5)0.000 (5)−0.021 (4)
C200.039 (3)0.057 (4)0.068 (4)0.003 (3)−0.006 (3)0.001 (3)
C210.119 (8)0.051 (4)0.081 (5)−0.008 (4)0.009 (5)0.018 (4)
C220.080 (5)0.093 (5)0.054 (4)−0.027 (4)−0.014 (4)0.021 (4)

Geometric parameters (Å, °)

Ni1—N12.059 (4)C7—C8'1.51 (4)
Ni1—N32.059 (4)C7—H7A0.9700
Ni1—O1W2.079 (4)C7—H7B0.9700
Ni1—O2W2.080 (4)C7—H7'A0.9700
Ni1—O12.104 (4)C7—H7'B0.9700
Ni1—O52.109 (4)C8—H7'B1.1455
N1—C31.321 (7)C8—H8A0.9600
N1—C11.379 (6)C8—H8B0.9600
N2—C31.349 (7)C8—H8C0.9600
N2—C21.357 (7)C8'—H8'10.9600
N2—H20.8600C8'—H8'20.9600
N3—C111.331 (7)C8'—H8'30.9600
N3—C91.371 (6)C9—C101.378 (7)
N4—C111.345 (6)C9—C121.471 (8)
N4—C101.391 (7)C10—C131.467 (7)
N4—H40.8600C11—C141.468 (8)
N5—C171.321 (8)C14—C151.555 (11)
N5—C191.420 (9)C14—H14A0.9700
N5—C181.454 (8)C14—H14B0.9700
N6—C201.307 (7)C15—C16'1.51 (3)
N6—C221.443 (8)C15—C161.52 (4)
N6—C211.466 (8)C15—H15A0.9700
O1—C41.259 (6)C15—H15B0.9700
O2—C41.265 (6)C15—H15C0.9700
O3—C51.300 (7)C15—H15D0.9700
O3—H11.05 (6)C16—H16A0.9600
O4—C51.226 (7)C16—H16B0.9600
O5—C121.258 (6)C16—H16C0.9600
O6—C121.263 (6)C16'—H16D0.9600
O7—C131.281 (7)C16'—H16E0.9600
O7—H70.8200C16'—H16F0.9600
O8—C131.229 (7)C17—H170.9300
O9—C171.228 (6)C18—H18A0.9600
O10—C201.230 (7)C18—H18B0.9600
O1W—H1W0.8500C18—H18C0.9600
O1W—H2W0.8500C19—H19A0.9600
O2W—H3W0.8501C19—H19B0.9600
O2W—H4W0.8500C19—H19C0.9600
C1—C21.370 (7)C20—H200.9300
C1—C41.474 (8)C21—H21A0.9600
C2—C51.471 (7)C21—H21B0.9600
C3—C61.487 (7)C21—H21C0.9600
C6—C71.555 (10)C22—H22A0.9600
C6—H6A0.9700C22—H22B0.9600
C6—H6B0.9700C22—H22C0.9600
C7—C81.463 (14)
N1—Ni1—N3179.6 (2)C7—C8—H8C109.5
N1—Ni1—O1W88.90 (16)C7—C8'—H8'1109.5
N3—Ni1—O1W91.00 (16)C7—C8'—H8'2109.5
N1—Ni1—O2W90.96 (16)H8'1—C8'—H8'2109.5
N3—Ni1—O2W89.13 (16)C7—C8'—H8'3109.5
O1W—Ni1—O2W179.68 (18)H8'1—C8'—H8'3109.5
N1—Ni1—O180.44 (15)H8'2—C8'—H8'3109.5
N3—Ni1—O199.99 (16)N3—C9—C10110.0 (5)
O1W—Ni1—O188.97 (14)N3—C9—C12118.2 (4)
O2W—Ni1—O190.72 (16)C10—C9—C12131.7 (5)
N1—Ni1—O599.23 (15)C9—C10—N4104.4 (4)
N3—Ni1—O580.33 (15)C9—C10—C13132.8 (5)
O1W—Ni1—O590.31 (16)N4—C10—C13122.6 (5)
O2W—Ni1—O590.00 (15)N3—C11—N4110.2 (5)
O1—Ni1—O5179.21 (17)N3—C11—C14126.3 (5)
C3—N1—C1106.1 (4)N4—C11—C14123.4 (5)
C3—N1—Ni1143.2 (4)O5—C12—O6124.2 (5)
C1—N1—Ni1110.7 (3)O5—C12—C9116.8 (5)
C3—N2—C2108.9 (4)O6—C12—C9119.0 (5)
C3—N2—H2125.6O8—C13—O7124.1 (5)
C2—N2—H2125.6O8—C13—C10119.8 (5)
C11—N3—C9106.7 (4)O7—C13—C10116.1 (5)
C11—N3—Ni1142.7 (4)C11—C14—C15111.1 (5)
C9—N3—Ni1110.6 (3)C11—C14—H14A109.4
C11—N4—C10108.7 (4)C15—C14—H14A109.4
C11—N4—H4125.6C11—C14—H14B109.4
C10—N4—H4125.6C15—C14—H14B109.4
C17—N5—C19122.1 (5)H14A—C14—H14B108.0
C17—N5—C18119.5 (6)C16'—C15—C14114.0 (14)
C19—N5—C18118.4 (6)C16—C15—C14109.9 (19)
C20—N6—C22120.8 (5)C16'—C15—H15A129.8
C20—N6—C21121.3 (6)C16—C15—H15A109.7
C22—N6—C21117.9 (6)C14—C15—H15A109.7
C4—O1—Ni1114.2 (3)C16—C15—H15B109.7
C4—O2—H1111 (2)C14—C15—H15B109.7
C5—O3—H1113 (3)H15A—C15—H15B108.2
C12—O5—Ni1114.0 (4)C16'—C15—H15C98.8
C13—O7—H7109.5C14—C15—H15C107.5
Ni1—O1W—H1W112.5C16'—C15—H15D119.5
Ni1—O1W—H2W125.5C14—C15—H15D108.6
H1W—O1W—H2W109.5H15C—C15—H15D107.2
Ni1—O2W—H3W105.4C15—C16—H16A109.5
Ni1—O2W—H4W106.7C15—C16—H16B109.5
H3W—O2W—H4W108.3C15—C16—H16C109.5
C2—C1—N1109.5 (5)C15—C16'—H16D109.5
C2—C1—C4132.8 (5)C15—C16'—H16E109.5
N1—C1—C4117.7 (4)H16D—C16'—H16E109.5
N2—C2—C1105.4 (4)C15—C16'—H16F109.5
N2—C2—C5122.6 (5)H16D—C16'—H16F109.5
C1—C2—C5131.9 (5)H16E—C16'—H16F109.5
N1—C3—N2110.2 (5)O9—C17—N5124.7 (6)
N1—C3—C6124.9 (5)O9—C17—H17117.7
N2—C3—C6124.9 (5)N5—C17—H17117.7
O1—C4—O2124.6 (5)N5—C18—H18A109.5
O1—C4—C1116.9 (5)N5—C18—H18B109.5
O2—C4—C1118.4 (5)H18A—C18—H18B109.5
O4—C5—O3123.9 (5)N5—C18—H18C109.5
O4—C5—C2119.6 (6)H18A—C18—H18C109.5
O3—C5—C2116.5 (5)H18B—C18—H18C109.5
C3—C6—C7112.9 (6)N5—C19—H19A109.5
C3—C6—H6A109.0N5—C19—H19B109.5
C7—C6—H6A109.0H19A—C19—H19B109.5
C3—C6—H6B109.0N5—C19—H19C109.5
C7—C6—H6B109.0H19A—C19—H19C109.5
H6A—C6—H6B107.8H19B—C19—H19C109.5
C8—C7—C6114.1 (9)O10—C20—N6125.2 (6)
C8'—C7—C6130.5 (19)O10—C20—H20117.4
C8—C7—H7A108.7N6—C20—H20117.4
C6—C7—H7A108.7N6—C21—H21A109.5
C8—C7—H7B108.7N6—C21—H21B109.5
C8'—C7—H7B120.0H21A—C21—H21B109.5
C6—C7—H7B108.7N6—C21—H21C109.5
H7A—C7—H7B107.6H21A—C21—H21C109.5
C8'—C7—H7'A106.8H21B—C21—H21C109.5
C6—C7—H7'A104.3N6—C22—H22A109.5
C8'—C7—H7'B103.8N6—C22—H22B109.5
C6—C7—H7'B104.0H22A—C22—H22B109.5
H7A—C7—H7'B147.0N6—C22—H22C109.5
H7'A—C7—H7'B105.4H22A—C22—H22C109.5
C7—C8—H8A109.5H22B—C22—H22C109.5
C7—C8—H8B109.5

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H1···O21.05 (6)1.42 (6)2.474 (6)176 (5)
O7—H7···O60.821.672.479 (6)169
N2—H2···O10i0.861.932.780 (6)171
N4—H4···O90.861.942.788 (6)171
O1W—H1W···O8ii0.851.962.782 (5)162
O1W—H2W···O10iii0.851.922.757 (6)168
O2W—H3W···O4iv0.851.962.794 (5)166
O2W—H4W···O9v0.851.982.800 (6)163

Symmetry codes: (i) x−1/2, −y−1/2, z−1; (ii) x, y−1, z; (iii) x, y, z−1; (iv) x, y+1, z; (v) x−1/2, −y+1/2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2277).

References

  • Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Jacobson, R. (1998). REQAB. Molecular Structure Corporation, The Woodlands, Texas, USA.
  • Johnson, C. K. (1976). ORTEPII Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, USA.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Song, W.-D., Yan, J.-B., Li, S.-J., Miao, D.-L. & Li, X.-F. (2010). Acta Cryst. E66, m53. [PMC free article] [PubMed]
  • Yan, J.-B., Li, S.-J., Song, W.-D., Wang, H. & Miao, D.-L. (2010). Acta Cryst. E66, m99. [PMC free article] [PubMed]

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