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A novel three-dimensional hydrogen-bonded complex, [Ni(C6H6N4)3](C8H4O4), was synthesized. Each Ni atom is six-coordinate, in a pseudo-octa­hedral geometry, formed by six N atoms of three chelating biimidazole ligands. It has a three-dimensional network structure, formed by extensive hydrogen bonds between [Ni(H2biim)3]2+ cations and phthalate anions. There are two cations and two anions in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030941/ww6413sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030941/ww6413Isup2.hkl
Contains datablock I

CCDC reference: 287754

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.043
  • wR factor = 0.146
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C SHFSU01_ALERT_2_C The absolute value of parameter shift to su ratio > 0.05 Absolute value of the parameter shift to su ratio given 0.052 Additional refinement cycles may be required. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.07 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 83.00 A   3 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N6 -H6A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N8 -H8A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.89(4), Rep 0.885(18) ...... 2.22 su-Rat N10 -H10A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.845(18) ...... 2.22 su-Rat N16 -H16A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N6 -H6A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.86(4), Rep 0.856(18) ...... 2.22 su-Rat N8 -H8A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(4), Rep 0.885(18) ...... 2.22 su-Rat N10 -H10A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(4), Rep 0.885(18) ...... 2.22 su-Rat N10 -H10A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.845(18) ...... 2.22 su-Rat N16 -H16A 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 9 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

In recent years, the controlled assembly of molecular building blocks to give three-dimensional nets connected via coordinative, hydrogen or covalent bonds, has been an important area for the development of molecular-based materials science (Ferey, 2001; Moulton & Zaworotko, 2002). 2,2'-Biimidazole (H2biim) possesses dual properties, namely coordination to metal centres and theability to act as a donor in hydrogen-bonding interactions (Fortin & Beauchamp, 2001; Sang et al., 2002; Atencio et al., 2004).

The structure of the title compound, (I), consists of [Ni(H2biim)3]2+ cations hydrogen bonded to phthalate dianions (Fig. 1). There are two molecules in the asymmetric unit. The coordination geometry of the nickel(II) centre can be described as distorted octahedral, formed by six N atoms from three chelating H2biim ligands. The main distortion results from the small N—Ni—N bite angles of the H2biim ligands, viz. 78.57 (8)–79.31 (8)° for [Ni1(H2biim)3]2+ and 79.07 (8)–79.57 (8)° for [Ni2(H2biim)3]2+ (Table 1). The Ni—N bond lengths are in the range 2.072 (2)–2.137 (2) Å. A similarly distorted octahedron has been reported previously for the analogous complex [NiII(Hbiim)3](NMe4) (NMe4 is tetramethylammonium), in which the Ni—N bond lengths are in the range of 1.96 (3)–2.19 (2) Å (Tadokoro et al., 1999).

Each [Ni1(H2bim)3]2+ complex cation is connected to three phthalate dianions through seven N—H···O hydrogen bonds, with N—O distances of 2.693 (3)–3.028 (3) Å (Table 2). In the hydrogen-bond environment of Ni2, however, each [Ni2(H2biim)3]2+ complex cation is connected through six strong N—H···O hydrogen bonds, with N—O distances of 2.674 (3)–2.788 (3) Å, to four phthalate dianions (Fig. 2). Through this complicated and dense three-dimensional network of hydrogen bonds, the crystal packing is formed (Fig. 3).

Experimental top

All reagents were of AR grade from commercial sources and used without further purification. Biimidazole was prepared following a slightly modified procedure (Ramirez et al., 2002) of Fieselmann et al. (1978). Ni(CH3COO)2 (124.43 mg, 0.5 mmol), phthalic acid (83.074 mg, 0.5 mmol) and H2biim (67.07 mg, 0.5 mmol) in a 1:1:1 molar ratio were added directly as a solid in deionized water (10 ml); after the mixture was stirred at room temperature for 30 min, a purple precipitate was obtained. The pH was adjusted to 7.0 using aqueous KOH solution. Then the mixture was placed in a 25 ml Teflon-lined stainless steel vessel and heated at 433 K for 4 d. The reaction vessel was allowed to cool to room temperature slowly, and purple crystals of title complex were obtained and collected by filtration and washed with water (yield 60%).

Refinement top

H atoms on C atoms were treated as riding, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq of the parent atom. H atoms on N atoms were refined with Uiso(H) = 0.08 Å and N—H distances in the range 0.84–0.90 Å. The final electron-density maximum and minimum are ?.?? and ?.??Å from atoms ?? and ??, respectively.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2000); program(s) used to refine structure: SHELXL97 (Sheldrick, 2000); molecular graphics: SHELXTL/PC (Sheldrick, 1999); software used to prepare material for publication: SHELXTL/PC.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. View of hydrogen-bonded (dashed line) interaction in the title complex.
[Figure 3] Fig. 3. A packing diagram of the title complex, viewed down the c axis.
Tris(2,2'-biimidazole)nickel(II) phthalate top
Crystal data top
[Ni(C6H6N4)3](C8H4O4)F(000) = 2576
Mr = 625.27Dx = 1.473 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7467 reflections
a = 23.5242 (18) Åθ = 2.4–24.2°
b = 11.1168 (9) ŵ = 0.74 mm1
c = 23.8578 (19) ÅT = 298 K
β = 115.325 (1)°Block, purple
V = 5639.5 (8) Å30.49 × 0.19 × 0.15 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
13575 independent reflections
Radiation source: fine-focus sealed tube9366 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
ϕ and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 1530
Tmin = 0.712, Tmax = 0.897k = 1414
34502 measured reflectionsl = 3127
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.086P)2 + 0.3746P]
where P = (Fo2 + 2Fc2)/3
13575 reflections(Δ/σ)max = 0.052
811 parametersΔρmax = 0.85 e Å3
12 restraintsΔρmin = 0.41 e Å3
Crystal data top
[Ni(C6H6N4)3](C8H4O4)V = 5639.5 (8) Å3
Mr = 625.27Z = 8
Monoclinic, P21/cMo Kα radiation
a = 23.5242 (18) ŵ = 0.74 mm1
b = 11.1168 (9) ÅT = 298 K
c = 23.8578 (19) Å0.49 × 0.19 × 0.15 mm
β = 115.325 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
13575 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
9366 reflections with I > 2σ(I)
Tmin = 0.712, Tmax = 0.897Rint = 0.029
34502 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04312 restraints
wR(F2) = 0.146H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.85 e Å3
13575 reflectionsΔρmin = 0.41 e Å3
811 parameters
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
Ni10.297972 (15)0.43282 (3)0.408920 (14)0.03367 (10)
Ni20.218476 (15)0.99385 (3)0.146530 (14)0.03460 (10)
N10.26147 (10)0.59208 (18)0.43033 (9)0.0367 (5)
N20.28603 (11)0.7669 (2)0.47927 (10)0.0435 (5)
N30.37989 (10)0.50533 (18)0.47939 (10)0.0377 (5)
N40.41950 (11)0.6427 (2)0.55256 (11)0.0479 (6)
N50.30319 (11)0.52657 (18)0.33531 (10)0.0389 (5)
N60.34006 (11)0.5351 (2)0.26440 (10)0.0403 (5)
N70.35223 (10)0.31181 (17)0.38177 (9)0.0362 (5)
N80.40765 (10)0.2910 (2)0.32733 (10)0.0391 (5)
N90.20945 (10)0.35107 (19)0.35689 (9)0.0401 (5)
N100.14189 (12)0.2119 (2)0.35506 (11)0.0553 (6)
N110.29316 (10)0.31317 (18)0.47335 (9)0.0386 (5)
N120.24568 (11)0.1590 (2)0.49308 (11)0.0434 (5)
N130.13287 (10)0.93047 (19)0.14267 (10)0.0405 (5)
N140.08147 (12)0.8645 (3)0.19503 (12)0.0624 (7)
N150.24260 (10)0.9692 (2)0.24232 (10)0.0401 (5)
N160.20404 (12)0.9506 (2)0.31144 (11)0.0501 (6)
N170.20183 (10)1.17884 (19)0.15165 (9)0.0401 (5)
N180.17531 (11)1.3507 (2)0.09995 (11)0.0468 (6)
N190.17682 (10)1.03775 (19)0.05296 (10)0.0393 (5)
N200.12721 (11)1.1743 (2)0.01800 (10)0.0409 (5)
N210.24696 (9)0.82579 (17)0.12880 (9)0.0353 (4)
N220.32457 (11)0.7124 (2)0.13068 (10)0.0427 (5)
N230.31277 (10)1.02870 (18)0.16627 (10)0.0378 (5)
N240.40652 (11)0.9503 (2)0.19168 (11)0.0447 (5)
O10.05404 (14)0.8068 (3)0.28947 (11)0.0933 (9)
O20.11296 (9)0.94959 (18)0.35324 (9)0.0486 (5)
O30.07251 (10)1.11458 (17)0.42695 (10)0.0542 (5)
O40.15186 (9)1.00862 (17)0.49594 (9)0.0515 (5)
O50.38970 (9)0.45284 (18)0.18420 (8)0.0452 (4)
O60.47094 (8)0.36130 (19)0.25923 (8)0.0492 (5)
O70.43473 (9)0.64905 (16)0.12601 (9)0.0478 (5)
O80.36762 (10)0.55685 (19)0.04029 (10)0.0600 (6)
C10.20933 (13)0.6636 (2)0.40975 (12)0.0426 (6)
H10.16980.64210.37980.051*
C20.22402 (14)0.7715 (3)0.43985 (13)0.0477 (7)
H20.19680.83570.43440.057*
C30.30681 (12)0.6582 (2)0.47202 (11)0.0368 (5)
C40.36914 (12)0.6076 (2)0.50169 (11)0.0369 (5)
C50.43941 (13)0.4727 (2)0.51891 (15)0.0499 (7)
H50.45980.40350.51530.060*
C60.46448 (14)0.5557 (3)0.56412 (16)0.0594 (8)
H60.50450.55430.59680.071*
C70.28361 (14)0.6318 (2)0.30273 (12)0.0460 (6)
H70.25900.69020.30970.055*
C80.30544 (14)0.6376 (3)0.25912 (13)0.0496 (7)
H80.29840.69950.23070.060*
C90.33727 (12)0.4707 (2)0.31076 (11)0.0342 (5)
C100.36553 (11)0.3573 (2)0.33751 (10)0.0327 (5)
C110.38889 (12)0.2096 (2)0.40123 (12)0.0414 (6)
H110.39000.15790.43230.050*
C120.42288 (12)0.1965 (2)0.36820 (12)0.0436 (6)
H120.45120.13510.37230.052*
C130.15663 (15)0.3584 (3)0.30223 (13)0.0576 (8)
H130.15070.41310.27070.069*
C140.11430 (16)0.2748 (3)0.30066 (14)0.0688 (10)
H140.07440.26240.26900.083*
C150.19849 (12)0.2621 (2)0.38807 (12)0.0390 (6)
C160.24462 (11)0.2397 (2)0.45072 (11)0.0362 (5)
C170.32740 (13)0.2781 (2)0.53414 (12)0.0444 (6)
H170.36460.31350.56200.053*
C180.29822 (13)0.1841 (3)0.54666 (12)0.0461 (6)
H180.31120.14410.58440.055*
C190.07590 (14)0.8848 (3)0.10163 (14)0.0575 (8)
H190.06130.88260.05870.069*
C200.04454 (15)0.8435 (4)0.13380 (15)0.0724 (10)
H200.00510.80740.11720.087*
C210.13457 (12)0.9152 (2)0.19808 (12)0.0415 (6)
C220.19219 (12)0.9448 (2)0.25164 (12)0.0388 (6)
C230.28938 (14)0.9928 (3)0.30009 (13)0.0538 (8)
H230.33061.01310.30860.065*
C240.26602 (15)0.9817 (3)0.34299 (14)0.0624 (9)
H240.28790.99310.38560.075*
C250.21510 (15)1.2718 (3)0.19319 (13)0.0525 (7)
H250.23251.26330.23610.063*
C260.19875 (15)1.3796 (3)0.16170 (14)0.0560 (8)
H260.20281.45600.17880.067*
C270.17784 (12)1.2301 (2)0.09596 (12)0.0367 (5)
C280.16079 (12)1.1532 (2)0.04266 (11)0.0359 (5)
C290.15252 (14)0.9837 (2)0.00390 (12)0.0455 (6)
H290.15650.90260.01120.055*
C300.12160 (14)1.0672 (2)0.04827 (13)0.0477 (7)
H300.10081.05410.09080.057*
C310.35753 (14)1.1166 (3)0.19275 (13)0.0482 (7)
H310.34941.19630.19880.058*
C320.41485 (14)1.0689 (3)0.20844 (15)0.0550 (8)
H320.45311.10920.22720.066*
C330.34427 (12)0.9302 (2)0.16647 (11)0.0350 (5)
C340.30770 (11)0.8219 (2)0.14281 (11)0.0344 (5)
C350.22364 (13)0.7145 (2)0.10483 (12)0.0426 (6)
H350.18180.69100.09010.051*
C360.27134 (13)0.6445 (2)0.10613 (13)0.0469 (7)
H360.26830.56510.09280.056*
C370.07202 (13)0.8687 (3)0.33813 (13)0.0482 (7)
C380.04347 (12)0.8393 (2)0.38218 (12)0.0409 (6)
C390.00462 (15)0.7397 (3)0.37028 (15)0.0586 (8)
H390.00350.69310.33530.070*
C400.02237 (15)0.7087 (3)0.41005 (17)0.0645 (9)
H400.04970.64350.40090.077*
C410.00859 (14)0.7742 (3)0.46246 (15)0.0572 (8)
H410.02610.75310.48940.069*
C420.03107 (13)0.8715 (3)0.47567 (13)0.0474 (6)
H420.04050.91530.51180.057*
C430.05732 (11)0.9054 (2)0.43567 (12)0.0361 (5)
C440.09702 (13)1.0175 (2)0.45293 (13)0.0402 (6)
C450.44221 (12)0.4013 (2)0.20466 (11)0.0361 (5)
C460.47283 (11)0.3811 (2)0.16111 (11)0.0349 (5)
C470.51591 (13)0.2876 (2)0.17329 (13)0.0460 (6)
H470.52690.24200.20910.055*
C480.54272 (15)0.2614 (3)0.13323 (15)0.0585 (8)
H480.57190.19950.14250.070*
C490.52631 (15)0.3268 (3)0.07977 (15)0.0578 (8)
H490.54350.30800.05220.069*
C500.48446 (14)0.4200 (3)0.06723 (13)0.0478 (7)
H500.47400.46470.03120.057*
C510.45730 (11)0.4492 (2)0.10702 (11)0.0356 (5)
C520.41561 (13)0.5587 (2)0.09025 (13)0.0408 (6)
H6A0.3501 (17)0.509 (3)0.2361 (14)0.080*
H22A0.3615 (11)0.688 (3)0.1316 (16)0.080*
H8A0.4211 (16)0.312 (3)0.3006 (13)0.080*
H16A0.1833 (15)0.934 (3)0.3318 (15)0.080*
H14A0.0716 (16)0.829 (3)0.2220 (13)0.080*
H12A0.2172 (13)0.110 (3)0.4896 (17)0.080*
H20A0.1104 (16)1.243 (2)0.0336 (16)0.080*
H18A0.1632 (17)1.396 (3)0.0679 (12)0.080*
H24A0.4395 (12)0.912 (3)0.1982 (17)0.080*
H4A0.4190 (17)0.707 (2)0.5732 (15)0.080*
H2A0.3131 (14)0.820 (3)0.5006 (15)0.080*
H10A0.1183 (14)0.164 (3)0.3661 (16)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.04099 (19)0.03020 (17)0.03391 (17)0.00446 (13)0.01993 (14)0.00233 (12)
Ni20.03643 (19)0.03113 (17)0.03620 (18)0.00230 (13)0.01550 (14)0.00068 (13)
N10.0400 (12)0.0371 (11)0.0349 (11)0.0005 (9)0.0178 (9)0.0014 (9)
N20.0478 (14)0.0362 (12)0.0445 (13)0.0033 (10)0.0177 (11)0.0056 (10)
N30.0391 (12)0.0325 (11)0.0444 (12)0.0029 (9)0.0206 (10)0.0067 (9)
N40.0447 (13)0.0404 (13)0.0521 (14)0.0014 (10)0.0144 (11)0.0146 (10)
N50.0516 (13)0.0318 (10)0.0397 (11)0.0019 (9)0.0257 (10)0.0002 (9)
N60.0499 (13)0.0416 (12)0.0350 (11)0.0039 (10)0.0235 (10)0.0005 (9)
N70.0439 (12)0.0301 (10)0.0359 (11)0.0053 (9)0.0184 (9)0.0030 (8)
N80.0389 (12)0.0405 (12)0.0402 (12)0.0046 (9)0.0192 (10)0.0067 (9)
N90.0471 (13)0.0389 (11)0.0353 (11)0.0051 (10)0.0186 (10)0.0015 (9)
N100.0536 (15)0.0609 (16)0.0458 (13)0.0223 (13)0.0159 (12)0.0017 (12)
N110.0409 (12)0.0382 (11)0.0394 (11)0.0053 (9)0.0196 (10)0.0003 (9)
N120.0445 (13)0.0370 (12)0.0514 (13)0.0036 (10)0.0232 (11)0.0070 (10)
N130.0351 (12)0.0461 (13)0.0378 (11)0.0015 (10)0.0132 (9)0.0024 (9)
N140.0423 (14)0.097 (2)0.0486 (15)0.0237 (14)0.0203 (12)0.0083 (14)
N150.0376 (12)0.0440 (12)0.0375 (11)0.0069 (10)0.0149 (10)0.0025 (9)
N160.0495 (14)0.0641 (16)0.0393 (13)0.0185 (12)0.0214 (11)0.0093 (11)
N170.0459 (13)0.0356 (11)0.0387 (11)0.0010 (10)0.0179 (10)0.0039 (9)
N180.0571 (15)0.0306 (11)0.0486 (13)0.0014 (10)0.0186 (12)0.0006 (10)
N190.0479 (13)0.0344 (11)0.0383 (11)0.0041 (10)0.0210 (10)0.0008 (9)
N200.0452 (13)0.0360 (11)0.0386 (11)0.0055 (10)0.0152 (10)0.0033 (9)
N210.0362 (11)0.0269 (10)0.0409 (11)0.0014 (8)0.0146 (9)0.0021 (8)
N220.0469 (13)0.0365 (11)0.0490 (13)0.0068 (10)0.0247 (11)0.0001 (10)
N230.0423 (12)0.0312 (10)0.0408 (11)0.0031 (9)0.0188 (10)0.0015 (9)
N240.0366 (12)0.0486 (14)0.0484 (13)0.0021 (10)0.0177 (11)0.0021 (11)
O10.118 (2)0.115 (2)0.0648 (15)0.0619 (19)0.0566 (15)0.0397 (15)
O20.0501 (12)0.0506 (11)0.0544 (12)0.0123 (9)0.0312 (10)0.0043 (9)
O30.0579 (13)0.0338 (10)0.0655 (13)0.0020 (9)0.0213 (10)0.0012 (9)
O40.0471 (12)0.0479 (11)0.0527 (12)0.0110 (9)0.0149 (10)0.0042 (9)
O50.0415 (10)0.0577 (12)0.0409 (10)0.0081 (9)0.0218 (8)0.0034 (9)
O60.0392 (10)0.0690 (13)0.0418 (10)0.0037 (9)0.0194 (8)0.0168 (9)
O70.0500 (11)0.0328 (9)0.0651 (12)0.0013 (8)0.0289 (10)0.0003 (9)
O80.0577 (13)0.0537 (13)0.0560 (13)0.0110 (10)0.0122 (11)0.0086 (10)
C10.0414 (15)0.0471 (15)0.0382 (13)0.0008 (12)0.0161 (12)0.0021 (12)
C20.0498 (17)0.0450 (15)0.0480 (16)0.0093 (13)0.0207 (13)0.0012 (12)
C30.0447 (15)0.0311 (12)0.0380 (13)0.0005 (11)0.0211 (11)0.0033 (10)
C40.0384 (14)0.0341 (12)0.0395 (13)0.0016 (11)0.0181 (11)0.0052 (10)
C50.0403 (15)0.0379 (14)0.0687 (19)0.0025 (12)0.0207 (14)0.0108 (13)
C60.0387 (16)0.0541 (18)0.068 (2)0.0035 (14)0.0065 (14)0.0132 (15)
C70.0601 (18)0.0351 (14)0.0494 (15)0.0073 (12)0.0297 (14)0.0064 (12)
C80.0657 (19)0.0427 (15)0.0435 (15)0.0057 (14)0.0262 (14)0.0121 (12)
C90.0398 (14)0.0335 (12)0.0322 (12)0.0053 (10)0.0181 (11)0.0030 (10)
C100.0341 (13)0.0316 (12)0.0323 (12)0.0070 (10)0.0140 (10)0.0069 (10)
C110.0454 (15)0.0316 (12)0.0435 (14)0.0033 (11)0.0155 (12)0.0004 (11)
C120.0414 (15)0.0351 (13)0.0508 (15)0.0022 (11)0.0164 (12)0.0016 (12)
C130.065 (2)0.068 (2)0.0350 (14)0.0082 (16)0.0167 (14)0.0049 (14)
C140.063 (2)0.086 (2)0.0413 (16)0.0248 (19)0.0069 (15)0.0001 (16)
C150.0438 (14)0.0362 (13)0.0403 (13)0.0058 (11)0.0211 (12)0.0030 (11)
C160.0382 (14)0.0330 (12)0.0407 (13)0.0008 (11)0.0202 (11)0.0002 (10)
C170.0412 (15)0.0464 (15)0.0406 (14)0.0025 (12)0.0126 (12)0.0048 (12)
C180.0430 (15)0.0494 (16)0.0415 (14)0.0028 (12)0.0138 (12)0.0133 (12)
C190.0417 (16)0.079 (2)0.0423 (16)0.0043 (15)0.0085 (13)0.0077 (15)
C200.0415 (17)0.113 (3)0.056 (2)0.0264 (19)0.0145 (15)0.0135 (19)
C210.0345 (13)0.0481 (15)0.0416 (14)0.0022 (11)0.0161 (11)0.0053 (12)
C220.0401 (14)0.0397 (13)0.0376 (13)0.0056 (11)0.0176 (11)0.0028 (11)
C230.0418 (16)0.070 (2)0.0461 (16)0.0166 (14)0.0155 (13)0.0062 (14)
C240.0515 (18)0.091 (3)0.0410 (16)0.0249 (17)0.0161 (14)0.0137 (16)
C250.067 (2)0.0468 (16)0.0414 (15)0.0008 (14)0.0215 (14)0.0094 (12)
C260.074 (2)0.0368 (15)0.0549 (17)0.0013 (14)0.0250 (16)0.0114 (13)
C270.0369 (13)0.0313 (12)0.0422 (13)0.0011 (10)0.0172 (11)0.0014 (10)
C280.0384 (13)0.0325 (12)0.0370 (13)0.0011 (10)0.0164 (11)0.0003 (10)
C290.0595 (18)0.0362 (14)0.0430 (15)0.0025 (12)0.0241 (14)0.0063 (11)
C300.0563 (18)0.0449 (15)0.0381 (14)0.0016 (13)0.0165 (13)0.0072 (12)
C310.0521 (17)0.0362 (14)0.0554 (17)0.0092 (13)0.0221 (14)0.0035 (12)
C320.0464 (17)0.0559 (18)0.0590 (18)0.0170 (14)0.0190 (14)0.0069 (15)
C330.0367 (13)0.0351 (13)0.0372 (13)0.0000 (10)0.0196 (11)0.0034 (10)
C340.0373 (13)0.0320 (12)0.0354 (12)0.0033 (10)0.0169 (11)0.0027 (10)
C350.0473 (15)0.0332 (13)0.0434 (14)0.0043 (12)0.0156 (12)0.0033 (11)
C360.0593 (18)0.0310 (13)0.0532 (16)0.0021 (12)0.0268 (14)0.0084 (12)
C370.0461 (16)0.0553 (17)0.0430 (15)0.0118 (14)0.0189 (13)0.0069 (13)
C380.0354 (14)0.0413 (13)0.0439 (14)0.0071 (11)0.0148 (11)0.0007 (11)
C390.0589 (19)0.0521 (17)0.0586 (18)0.0201 (15)0.0191 (15)0.0053 (14)
C400.0549 (19)0.0560 (19)0.081 (2)0.0229 (15)0.0280 (18)0.0052 (17)
C410.0488 (17)0.065 (2)0.064 (2)0.0038 (15)0.0303 (15)0.0170 (16)
C420.0452 (16)0.0497 (16)0.0543 (16)0.0009 (13)0.0279 (13)0.0028 (13)
C430.0325 (13)0.0346 (12)0.0426 (13)0.0002 (10)0.0173 (11)0.0039 (11)
C440.0436 (15)0.0369 (14)0.0455 (15)0.0050 (11)0.0243 (13)0.0037 (11)
C450.0352 (13)0.0355 (12)0.0392 (13)0.0034 (11)0.0174 (11)0.0021 (10)
C460.0338 (13)0.0311 (12)0.0408 (13)0.0018 (10)0.0168 (11)0.0000 (10)
C470.0458 (16)0.0385 (14)0.0524 (16)0.0079 (12)0.0199 (13)0.0074 (12)
C480.0580 (19)0.0493 (17)0.071 (2)0.0162 (15)0.0305 (17)0.0028 (15)
C490.064 (2)0.0582 (19)0.066 (2)0.0063 (16)0.0424 (17)0.0081 (16)
C500.0539 (17)0.0488 (16)0.0495 (16)0.0011 (13)0.0303 (14)0.0008 (13)
C510.0375 (13)0.0312 (12)0.0402 (13)0.0048 (10)0.0187 (11)0.0020 (10)
C520.0443 (15)0.0344 (13)0.0517 (16)0.0002 (11)0.0281 (13)0.0096 (12)
Geometric parameters (Å, º) top
Ni1—N112.072 (2)O2—C371.252 (3)
Ni1—N52.090 (2)O3—C441.255 (3)
Ni1—N32.102 (2)O4—C441.263 (3)
Ni1—N92.119 (2)O5—C451.255 (3)
Ni1—N12.123 (2)O6—C451.264 (3)
Ni1—N72.137 (2)O7—C521.269 (3)
Ni2—N192.076 (2)O8—C521.243 (3)
Ni2—N212.088 (2)C1—C21.364 (4)
Ni2—N232.097 (2)C1—H10.9300
Ni2—N132.098 (2)C2—H20.9300
Ni2—N172.107 (2)C3—C41.442 (4)
Ni2—N152.124 (2)C5—C61.349 (4)
N1—C31.326 (3)C5—H50.9300
N1—C11.365 (3)C6—H60.9300
N2—C31.342 (3)C7—C81.344 (4)
N2—C21.357 (4)C7—H70.9300
N2—H2A0.854 (18)C8—H80.9300
N3—C41.325 (3)C9—C101.441 (3)
N3—C51.361 (3)C11—C121.349 (4)
N4—C41.341 (3)C11—H110.9300
N4—C61.371 (4)C12—H120.9300
N4—H4A0.875 (18)C13—C141.351 (4)
N5—C91.331 (3)C13—H130.9300
N5—C71.371 (3)C14—H140.9300
N6—C91.342 (3)C15—C161.445 (4)
N6—C81.375 (4)C17—C181.352 (4)
N6—H6A0.856 (18)C17—H170.9300
N7—C101.324 (3)C18—H180.9300
N7—C111.381 (3)C19—C201.352 (5)
N8—C101.338 (3)C19—H190.9300
N8—C121.372 (3)C20—H200.9300
N8—H8A0.856 (18)C21—C221.448 (4)
N9—C151.327 (3)C23—C241.359 (4)
N9—C131.366 (4)C23—H230.9300
N10—C151.345 (3)C24—H240.9300
N10—C141.369 (4)C25—C261.379 (4)
N10—H10A0.885 (18)C25—H250.9300
N11—C161.317 (3)C26—H260.9300
N11—C171.380 (3)C27—C281.439 (3)
N12—C161.344 (3)C29—C301.361 (4)
N12—C181.374 (4)C29—H290.9300
N12—H12A0.843 (18)C30—H300.9300
N13—C211.316 (3)C31—C321.344 (4)
N13—C191.375 (4)C31—H310.9300
N14—C211.344 (3)C32—H320.9300
N14—C201.363 (4)C33—C341.447 (3)
N14—H14A0.865 (18)C35—C361.355 (4)
N15—C221.325 (3)C35—H350.9300
N15—C231.372 (3)C36—H360.9300
N16—C221.333 (3)C37—C381.506 (4)
N16—C241.369 (4)C38—C391.385 (4)
N16—H16A0.845 (18)C38—C431.385 (4)
N17—C271.329 (3)C39—C401.392 (5)
N17—C251.372 (3)C39—H390.9300
N18—C271.348 (3)C40—C411.361 (5)
N18—C261.372 (4)C40—H400.9300
N18—H18A0.853 (18)C41—C421.374 (4)
N19—C281.331 (3)C41—H410.9300
N19—C291.366 (3)C42—C431.392 (3)
N20—C281.340 (3)C42—H420.9300
N20—C301.369 (3)C43—C441.506 (3)
N20—H20A0.872 (18)C45—C461.513 (3)
N21—C341.322 (3)C46—C471.392 (3)
N21—C351.375 (3)C46—C511.403 (3)
N22—C341.349 (3)C47—C481.383 (4)
N22—C361.362 (3)C47—H470.9300
N22—H22A0.902 (18)C48—C491.372 (4)
N23—C331.321 (3)C48—H480.9300
N23—C311.376 (3)C49—C501.371 (4)
N24—C331.343 (3)C49—H490.9300
N24—C321.368 (4)C50—C511.391 (4)
N24—H24A0.841 (18)C50—H500.9300
O1—C371.257 (3)C51—C521.506 (3)
N11—Ni1—N5169.97 (8)N7—C10—N8112.3 (2)
N11—Ni1—N388.58 (8)N7—C10—C9117.8 (2)
N5—Ni1—N396.75 (8)N8—C10—C9129.7 (2)
N11—Ni1—N978.90 (8)C12—C11—N7109.5 (2)
N5—Ni1—N996.76 (8)C12—C11—H11125.3
N3—Ni1—N9165.43 (8)N7—C11—H11125.3
N11—Ni1—N1101.58 (8)C11—C12—N8107.0 (2)
N5—Ni1—N187.79 (8)C11—C12—H12126.5
N3—Ni1—N179.31 (8)N8—C12—H12126.5
N9—Ni1—N195.82 (8)C14—C13—N9110.1 (3)
N11—Ni1—N792.87 (8)C14—C13—H13124.9
N5—Ni1—N778.57 (8)N9—C13—H13124.9
N3—Ni1—N791.25 (8)C13—C14—N10106.3 (3)
N9—Ni1—N796.73 (8)C13—C14—H14126.9
N1—Ni1—N7162.44 (8)N10—C14—H14126.9
N19—Ni2—N2192.13 (8)N9—C15—N10111.2 (2)
N19—Ni2—N2399.52 (8)N9—C15—C16118.0 (2)
N21—Ni2—N2379.07 (8)N10—C15—C16130.7 (2)
N19—Ni2—N1391.66 (9)N11—C16—N12111.8 (2)
N21—Ni2—N1394.35 (8)N11—C16—C15116.9 (2)
N23—Ni2—N13167.17 (8)N12—C16—C15131.1 (2)
N19—Ni2—N1779.57 (8)C18—C17—N11109.1 (2)
N21—Ni2—N17165.64 (8)C18—C17—H17125.5
N23—Ni2—N1790.67 (8)N11—C17—H17125.5
N13—Ni2—N1797.57 (8)C17—C18—N12106.9 (2)
N19—Ni2—N15166.75 (8)C17—C18—H18126.5
N21—Ni2—N1598.11 (8)N12—C18—H18126.5
N23—Ni2—N1590.70 (8)C20—C19—N13108.9 (3)
N13—Ni2—N1579.25 (8)C20—C19—H19125.6
N17—Ni2—N1591.98 (8)N13—C19—H19125.6
C3—N1—C1104.9 (2)C19—C20—N14107.3 (3)
C3—N1—Ni1111.36 (16)C19—C20—H20126.3
C1—N1—Ni1142.47 (18)N14—C20—H20126.3
C3—N2—C2106.7 (2)N13—C21—N14111.8 (2)
C3—N2—H2A118 (2)N13—C21—C22118.2 (2)
C2—N2—H2A134 (2)N14—C21—C22129.8 (3)
C4—N3—C5105.5 (2)N15—C22—N16112.2 (2)
C4—N3—Ni1112.54 (17)N15—C22—C21117.7 (2)
C5—N3—Ni1140.50 (17)N16—C22—C21130.1 (2)
C4—N4—C6106.5 (2)C24—C23—N15109.3 (3)
C4—N4—H4A122 (2)C24—C23—H23125.3
C6—N4—H4A131 (2)N15—C23—H23125.3
C9—N5—C7105.5 (2)C23—C24—N16106.7 (3)
C9—N5—Ni1113.58 (16)C23—C24—H24126.6
C7—N5—Ni1140.87 (18)N16—C24—H24126.6
C9—N6—C8106.4 (2)N17—C25—C26109.7 (2)
C9—N6—H6A126 (3)N17—C25—H25125.2
C8—N6—H6A124 (3)C26—C25—H25125.2
C10—N7—C11104.8 (2)N18—C26—C25105.8 (2)
C10—N7—Ni1112.14 (16)N18—C26—H26127.1
C11—N7—Ni1141.64 (17)C25—C26—H26127.1
C10—N8—C12106.4 (2)N17—C27—N18111.6 (2)
C10—N8—H8A121 (2)N17—C27—C28117.9 (2)
C12—N8—H8A132 (2)N18—C27—C28130.5 (2)
C15—N9—C13105.3 (2)N19—C28—N20111.0 (2)
C15—N9—Ni1111.65 (17)N19—C28—C27117.4 (2)
C13—N9—Ni1142.97 (19)N20—C28—C27131.5 (2)
C15—N10—C14107.0 (2)C30—C29—N19109.2 (2)
C15—N10—H10A132 (2)C30—C29—H29125.4
C14—N10—H10A119 (2)N19—C29—H29125.4
C16—N11—C17105.6 (2)C29—C30—N20106.5 (2)
C16—N11—Ni1114.01 (16)C29—C30—H30126.7
C17—N11—Ni1140.20 (18)N20—C30—H30126.7
C16—N12—C18106.5 (2)C32—C31—N23109.1 (3)
C16—N12—H12A127 (3)C32—C31—H31125.5
C18—N12—H12A126 (3)N23—C31—H31125.5
C21—N13—C19105.6 (2)C31—C32—N24107.3 (3)
C21—N13—Ni2112.52 (17)C31—C32—H32126.3
C19—N13—Ni2141.29 (19)N24—C32—H32126.3
C21—N14—C20106.4 (3)N23—C33—N24111.5 (2)
C21—N14—H14A134 (2)N23—C33—C34116.7 (2)
C20—N14—H14A118 (2)N24—C33—C34131.8 (2)
C22—N15—C23105.1 (2)N21—C34—N22111.2 (2)
C22—N15—Ni2111.15 (17)N21—C34—C33118.0 (2)
C23—N15—Ni2141.88 (19)N22—C34—C33130.8 (2)
C22—N16—C24106.7 (2)C36—C35—N21109.2 (2)
C22—N16—H16A134 (3)C36—C35—H35125.4
C24—N16—H16A119 (3)N21—C35—H35125.4
C27—N17—C25105.5 (2)C35—C36—N22106.9 (2)
C27—N17—Ni2111.72 (16)C35—C36—H36126.5
C25—N17—Ni2141.86 (19)N22—C36—H36126.5
C27—N18—C26107.4 (2)O2—C37—O1124.9 (3)
C27—N18—H18A122 (3)O2—C37—C38118.2 (2)
C26—N18—H18A131 (3)O1—C37—C38116.8 (2)
C28—N19—C29106.0 (2)C39—C38—C43119.2 (3)
C28—N19—Ni2113.04 (16)C39—C38—C37118.9 (3)
C29—N19—Ni2140.27 (18)C43—C38—C37121.9 (2)
C28—N20—C30107.3 (2)C38—C39—C40120.8 (3)
C28—N20—H20A124 (2)C38—C39—H39119.6
C30—N20—H20A128 (2)C40—C39—H39119.6
C34—N21—C35105.7 (2)C41—C40—C39119.6 (3)
C34—N21—Ni2112.60 (15)C41—C40—H40120.2
C35—N21—Ni2141.61 (18)C39—C40—H40120.2
C34—N22—C36107.0 (2)C40—C41—C42120.2 (3)
C34—N22—H22A129 (2)C40—C41—H41119.9
C36—N22—H22A123 (2)C42—C41—H41119.9
C33—N23—C31105.6 (2)C41—C42—C43120.8 (3)
C33—N23—Ni2112.66 (16)C41—C42—H42119.6
C31—N23—Ni2139.66 (19)C43—C42—H42119.6
C33—N24—C32106.5 (2)C38—C43—C42119.3 (2)
C33—N24—H24A138 (3)C38—C43—C44124.4 (2)
C32—N24—H24A116 (3)C42—C43—C44116.2 (2)
C2—C1—N1109.7 (2)O3—C44—O4124.2 (2)
C2—C1—H1125.2O3—C44—C43118.5 (2)
N1—C1—H1125.2O4—C44—C43117.1 (2)
N2—C2—C1106.6 (2)O5—C45—O6124.4 (2)
N2—C2—H2126.7O5—C45—C46118.6 (2)
C1—C2—H2126.7O6—C45—C46116.9 (2)
N1—C3—N2112.0 (2)C47—C46—C51118.3 (2)
N1—C3—C4118.4 (2)C47—C46—C45119.0 (2)
N2—C3—C4129.6 (2)C51—C46—C45122.6 (2)
N3—C4—N4111.5 (2)C48—C47—C46121.3 (3)
N3—C4—C3117.8 (2)C48—C47—H47119.4
N4—C4—C3130.5 (2)C46—C47—H47119.4
C6—C5—N3109.9 (2)C49—C48—C47120.1 (3)
C6—C5—H5125.1C49—C48—H48120.0
N3—C5—H5125.1C47—C48—H48120.0
C5—C6—N4106.6 (3)C50—C49—C48119.6 (3)
C5—C6—H6126.7C50—C49—H49120.2
N4—C6—H6126.7C48—C49—H49120.2
C8—C7—N5109.4 (2)C49—C50—C51121.6 (3)
C8—C7—H7125.3C49—C50—H50119.2
N5—C7—H7125.3C51—C50—H50119.2
C7—C8—N6107.3 (2)C50—C51—C46119.1 (2)
C7—C8—H8126.4C50—C51—C52116.4 (2)
N6—C8—H8126.4C46—C51—C52124.4 (2)
N5—C9—N6111.4 (2)O8—C52—O7125.0 (2)
N5—C9—C10117.6 (2)O8—C52—C51117.5 (2)
N6—C9—C10131.0 (2)O7—C52—C51117.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O8i0.85 (2)1.84 (2)2.693 (3)175 (4)
N4—H4A···O7i0.88 (2)1.97 (2)2.832 (3)169 (3)
N6—H6A···O50.86 (2)1.94 (2)2.788 (3)169 (4)
N8—H8A···O60.86 (2)1.91 (2)2.745 (3)165 (3)
N10—H10A···O2ii0.89 (2)2.40 (3)2.990 (3)124 (3)
N10—H10A···O3ii0.89 (2)2.22 (2)3.028 (3)152 (3)
N12—H12A···O4ii0.84 (2)1.96 (2)2.792 (3)169 (4)
N14—H14A···O10.87 (2)1.84 (2)2.674 (3)161 (4)
N16—H16A···O20.85 (2)1.94 (2)2.723 (3)154 (4)
N18—H18A···O4iii0.85 (2)1.94 (2)2.781 (3)169 (4)
N20—H20A···O3iii0.87 (2)1.86 (2)2.728 (3)175 (3)
N22—H22A···O70.90 (2)1.84 (2)2.733 (3)174 (3)
N24—H24A···O6iv0.84 (2)1.99 (2)2.788 (3)158 (4)
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y1, z; (iii) x, y+5/2, z1/2; (iv) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula[Ni(C6H6N4)3](C8H4O4)
Mr625.27
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)23.5242 (18), 11.1168 (9), 23.8578 (19)
β (°) 115.325 (1)
V3)5639.5 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.74
Crystal size (mm)0.49 × 0.19 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.712, 0.897
No. of measured, independent and
observed [I > 2σ(I)] reflections
34502, 13575, 9366
Rint0.029
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.146, 1.05
No. of reflections13575
No. of parameters811
No. of restraints12
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.85, 0.41

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 2000), SHELXL97 (Sheldrick, 2000), SHELXTL/PC (Sheldrick, 1999), SHELXTL/PC.

Selected geometric parameters (Å, º) top
Ni1—N112.072 (2)Ni2—N192.076 (2)
Ni1—N52.090 (2)Ni2—N212.088 (2)
Ni1—N32.102 (2)Ni2—N232.097 (2)
Ni1—N92.119 (2)Ni2—N132.098 (2)
Ni1—N12.123 (2)Ni2—N172.107 (2)
Ni1—N72.137 (2)Ni2—N152.124 (2)
N11—Ni1—N5169.97 (8)N19—Ni2—N2192.13 (8)
N11—Ni1—N388.58 (8)N19—Ni2—N2399.52 (8)
N5—Ni1—N396.75 (8)N21—Ni2—N2379.07 (8)
N11—Ni1—N978.90 (8)N19—Ni2—N1391.66 (9)
N5—Ni1—N996.76 (8)N21—Ni2—N1394.35 (8)
N3—Ni1—N9165.43 (8)N23—Ni2—N13167.17 (8)
N11—Ni1—N1101.58 (8)N19—Ni2—N1779.57 (8)
N5—Ni1—N187.79 (8)N21—Ni2—N17165.64 (8)
N3—Ni1—N179.31 (8)N23—Ni2—N1790.67 (8)
N9—Ni1—N195.82 (8)N13—Ni2—N1797.57 (8)
N11—Ni1—N792.87 (8)N19—Ni2—N15166.75 (8)
N5—Ni1—N778.57 (8)N21—Ni2—N1598.11 (8)
N3—Ni1—N791.25 (8)N23—Ni2—N1590.70 (8)
N9—Ni1—N796.73 (8)N13—Ni2—N1579.25 (8)
N1—Ni1—N7162.44 (8)N17—Ni2—N1591.98 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O8i0.854 (18)1.842 (19)2.693 (3)175 (4)
N4—H4A···O7i0.875 (18)1.968 (19)2.832 (3)169 (3)
N6—H6A···O50.856 (18)1.94 (2)2.788 (3)169 (4)
N8—H8A···O60.856 (18)1.91 (2)2.745 (3)165 (3)
N10—H10A···O2ii0.885 (18)2.40 (3)2.990 (3)124 (3)
N10—H10A···O3ii0.885 (18)2.22 (2)3.028 (3)152 (3)
N12—H12A···O4ii0.843 (18)1.960 (19)2.792 (3)169 (4)
N14—H14A···O10.865 (18)1.84 (2)2.674 (3)161 (4)
N16—H16A···O20.845 (18)1.94 (2)2.723 (3)154 (4)
N18—H18A···O4iii0.853 (18)1.94 (2)2.781 (3)169 (4)
N20—H20A···O3iii0.872 (18)1.858 (19)2.728 (3)175 (3)
N22—H22A···O70.902 (18)1.835 (19)2.733 (3)174 (3)
N24—H24A···O6iv0.841 (18)1.99 (2)2.788 (3)158 (4)
Symmetry codes: (i) x, y+3/2, z+1/2; (ii) x, y1, z; (iii) x, y+5/2, z1/2; (iv) x+1, y+1/2, z+1/2.
 

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