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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1631–m1632.
Published online 2009 November 21. doi:  10.1107/S1600536809048363
PMCID: PMC2971780

Ammonium tris­(3-amino­pyrazine-2-carboxyl­ato-κ2 N 1,O)nickelate(II) trihydrate

Abstract

The NiII atom in the title hydrated salt, (NH4)[Ni(C5H4N3O2)3]·3H2O, is N,O-chelated by the three 3-aminopyrazine-2-carboxyl­ate ligands, resulting in a distorted octa­hedral mer-NiN3O3 geometry for the metal. In the crystal, the complex anion, ammonium cation and uncoordinated water mol­ecules are linked by extensive N—H(...)N, N—H(...)O, O—H(...)N and O—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For the crystal structure of diaqua­bis(3-amino­pyrazine-2-carboxyl­ato)nickel(II), see: Ptasiewicz-Bak & Leciejewicz (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1631-scheme1.jpg

Experimental

Crystal data

  • (NH4)[Ni(C5H4N3O2)3]·3H2O
  • M r = 545.14
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1631-efi1.jpg
  • a = 11.2092 (3) Å
  • b = 14.7061 (4) Å
  • c = 13.7540 (4) Å
  • β = 97.5214 (8)°
  • V = 2247.75 (11) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.93 mm−1
  • T = 293 K
  • 0.28 × 0.22 × 0.19 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.780, T max = 0.843
  • 21341 measured reflections
  • 5114 independent reflections
  • 4322 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.096
  • S = 1.02
  • 5114 reflections
  • 380 parameters
  • 25 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.47 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO data reduction: CrystalClear (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048363/hb5228sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048363/hb5228Isup2.hkl

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

Acknowledgments

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Scientific Fund of Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Nickel dichloride hexahydrate (0.48 g, 2 mmol), 3-aminopyrazine-2-carboxylic acid (0.56 g, 4 mmol) and sodium hydroxide (0.16 g 4 mmol) were dissolved in a water/DMF (v/v = 10 ml:1 ml) mixture. The solution was sealed in a 50 ml Teflon-lined stainless steel bomb and held at 443 K for 3 days. The bomb was gradually cooled to room temperature;, and green blocks of (I) were obtained after several days. The presence of the ammonium counterion is explained by the decomposition of DMF.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93 Å) and were included in the refinement in the riding model approximation, with U(H) = 1.2U(C). The amino and water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H = O–H = 0.85±0.01 Å; their Uiso values were refined.

Figures

Fig. 1.
The molecular structure of (I) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

(NH4)[Ni(C5H4N3O2)3]·3H2OF(000) = 1128
Mr = 545.14Dx = 1.611 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 17239 reflections
a = 11.2092 (3) Åθ = 3.2–27.5°
b = 14.7061 (4) ŵ = 0.93 mm1
c = 13.7540 (4) ÅT = 293 K
β = 97.5214 (8)°Block, green
V = 2247.75 (11) Å30.28 × 0.22 × 0.19 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP diffractometer5114 independent reflections
Radiation source: fine-focus sealed tube4322 reflections with I > 2σ(I)
graphiteRint = 0.028
ω scanθmax = 27.4°, θmin = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −14→14
Tmin = 0.780, Tmax = 0.843k = −19→19
21341 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0582P)2 + 0.5222P] where P = (Fo2 + 2Fc2)/3
5114 reflections(Δ/σ)max = 0.001
380 parametersΔρmax = 0.47 e Å3
25 restraintsΔρmin = −0.26 e Å3

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

xyzUiso*/Ueq
Ni10.31748 (2)0.668273 (15)0.689311 (16)0.03143 (9)
O10.42705 (12)0.74401 (9)0.78914 (10)0.0399 (3)
O20.46912 (13)0.77268 (10)0.94948 (10)0.0483 (3)
O30.37891 (13)0.72843 (9)0.57068 (10)0.0446 (3)
O40.33775 (17)0.83556 (12)0.45711 (12)0.0616 (5)
O50.21564 (11)0.57245 (9)0.60709 (9)0.0391 (3)
O60.22619 (12)0.43404 (11)0.54208 (12)0.0536 (4)
O1W0.5686 (2)0.8674 (2)0.67787 (15)0.0930 (8)
O2W0.53958 (16)1.06663 (15)0.88906 (13)0.0643 (5)
O3W0.3437 (3)0.8148 (3)0.25454 (17)0.0980 (8)
N10.25466 (14)0.62854 (10)0.81904 (11)0.0341 (3)
N20.15754 (17)0.62107 (13)0.99403 (13)0.0500 (4)
N30.2905 (2)0.73064 (15)1.06019 (13)0.0525 (5)
N40.19233 (13)0.77229 (10)0.65903 (10)0.0327 (3)
N50.03798 (15)0.91375 (11)0.59648 (12)0.0410 (4)
N60.14458 (19)0.94291 (14)0.46855 (15)0.0560 (5)
N70.44529 (13)0.56953 (10)0.67977 (10)0.0307 (3)
N80.60635 (14)0.44427 (11)0.62184 (12)0.0389 (4)
N90.45018 (16)0.36067 (12)0.54171 (13)0.0418 (4)
N100.6367 (2)0.88322 (17)0.87878 (16)0.0609 (5)
C10.40689 (16)0.73693 (12)0.87734 (13)0.0352 (4)
C20.30163 (16)0.67882 (12)0.89515 (13)0.0331 (4)
C30.25094 (18)0.67630 (13)0.98471 (14)0.0389 (4)
C40.1158 (2)0.56992 (16)0.91715 (16)0.0528 (5)
H40.05210.53070.92290.063*
C50.16254 (19)0.57242 (14)0.82959 (15)0.0429 (4)
H50.13050.53540.77780.052*
C60.31612 (18)0.79401 (13)0.53101 (13)0.0385 (4)
C70.21035 (17)0.82128 (11)0.58056 (13)0.0321 (4)
C80.13109 (17)0.89357 (12)0.54759 (13)0.0368 (4)
C90.02365 (18)0.86309 (14)0.67384 (14)0.0413 (4)
H9−0.04100.87580.70770.050*
C100.09911 (17)0.79277 (14)0.70670 (13)0.0390 (4)
H100.08550.75960.76180.047*
C110.27182 (16)0.50055 (13)0.58777 (13)0.0345 (4)
C120.40521 (15)0.49993 (12)0.62341 (12)0.0294 (3)
C130.48649 (16)0.43358 (12)0.59462 (12)0.0316 (4)
C140.64164 (17)0.51541 (14)0.67792 (15)0.0418 (4)
H140.72370.52350.69700.050*
C150.56347 (16)0.57786 (13)0.70937 (14)0.0379 (4)
H150.59240.62520.75070.045*
H1W10.518 (4)0.826 (3)0.681 (3)0.16 (2)*
H1W20.587 (4)0.871 (3)0.6200 (14)0.138 (16)*
H2W10.4664 (10)1.071 (2)0.8988 (19)0.079 (10)*
H2W20.586 (2)1.078 (3)0.9408 (15)0.123 (15)*
H3W10.366 (6)0.861 (2)0.290 (3)0.20 (3)*
H3W20.325 (6)0.772 (3)0.292 (3)0.21 (3)*
H310.3539 (16)0.7617 (16)1.056 (2)0.064 (8)*
H320.259 (2)0.724 (2)1.1133 (13)0.076 (9)*
H610.2078 (15)0.9305 (16)0.4426 (16)0.054 (7)*
H620.0924 (18)0.9821 (13)0.4466 (18)0.058 (7)*
H910.3745 (10)0.3567 (18)0.5212 (19)0.059 (7)*
H920.5008 (17)0.3270 (13)0.5183 (17)0.048 (7)*
H1010.592 (2)0.8458 (15)0.9058 (17)0.079 (10)*
H1020.627 (3)0.871 (2)0.8169 (8)0.106 (13)*
H1030.612 (3)0.9371 (9)0.887 (2)0.16 (2)*
H1040.7095 (10)0.876 (2)0.902 (2)0.124 (15)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ni10.03054 (14)0.03344 (14)0.03110 (13)0.00615 (9)0.00699 (9)0.00153 (9)
O10.0392 (7)0.0421 (7)0.0402 (7)−0.0052 (6)0.0123 (6)−0.0010 (6)
O20.0463 (8)0.0536 (8)0.0440 (7)−0.0107 (7)0.0029 (6)−0.0063 (7)
O30.0452 (8)0.0472 (7)0.0454 (7)0.0188 (6)0.0214 (6)0.0114 (6)
O40.0649 (11)0.0760 (11)0.0496 (9)0.0243 (9)0.0285 (8)0.0262 (8)
O50.0292 (6)0.0472 (7)0.0400 (7)0.0099 (6)0.0012 (5)−0.0059 (6)
O60.0326 (7)0.0540 (9)0.0713 (10)0.0016 (6)−0.0046 (7)−0.0237 (8)
O1W0.0979 (17)0.131 (2)0.0520 (11)−0.0539 (16)0.0174 (11)−0.0013 (12)
O2W0.0414 (9)0.0925 (13)0.0577 (10)−0.0038 (9)0.0021 (8)−0.0103 (10)
O3W0.0917 (18)0.144 (2)0.0590 (12)−0.0021 (17)0.0121 (12)−0.0216 (15)
N10.0345 (8)0.0350 (8)0.0325 (7)0.0019 (6)0.0037 (6)0.0027 (6)
N20.0528 (11)0.0581 (11)0.0419 (9)−0.0058 (9)0.0163 (8)0.0059 (8)
N30.0585 (12)0.0643 (12)0.0360 (9)−0.0039 (10)0.0113 (9)−0.0049 (9)
N40.0335 (8)0.0342 (7)0.0312 (7)0.0067 (6)0.0067 (6)−0.0003 (6)
N50.0408 (9)0.0391 (8)0.0427 (8)0.0131 (7)0.0042 (7)−0.0013 (7)
N60.0556 (12)0.0564 (11)0.0582 (11)0.0224 (10)0.0161 (10)0.0245 (10)
N70.0276 (7)0.0340 (7)0.0303 (7)0.0042 (6)0.0032 (6)0.0011 (6)
N80.0298 (8)0.0432 (8)0.0443 (8)0.0071 (7)0.0074 (7)0.0015 (7)
N90.0349 (9)0.0419 (9)0.0498 (9)0.0042 (7)0.0107 (8)−0.0092 (8)
N100.0507 (12)0.0779 (16)0.0551 (12)−0.0199 (11)0.0108 (10)−0.0007 (11)
C10.0343 (9)0.0340 (9)0.0374 (9)0.0032 (7)0.0053 (7)−0.0006 (8)
C20.0325 (9)0.0349 (9)0.0317 (8)0.0058 (7)0.0037 (7)0.0029 (7)
C30.0408 (10)0.0432 (10)0.0329 (9)0.0067 (8)0.0054 (8)0.0042 (8)
C40.0518 (13)0.0584 (13)0.0501 (12)−0.0145 (11)0.0138 (10)0.0067 (11)
C50.0442 (11)0.0436 (10)0.0407 (10)−0.0084 (9)0.0046 (8)0.0021 (8)
C60.0408 (10)0.0426 (10)0.0335 (9)0.0070 (8)0.0104 (8)0.0023 (8)
C70.0338 (9)0.0319 (8)0.0306 (8)0.0043 (7)0.0039 (7)−0.0011 (7)
C80.0387 (10)0.0340 (9)0.0368 (9)0.0043 (8)0.0014 (8)0.0007 (7)
C90.0376 (10)0.0478 (11)0.0393 (9)0.0113 (9)0.0084 (8)−0.0069 (9)
C100.0387 (10)0.0461 (10)0.0339 (9)0.0089 (8)0.0111 (8)−0.0001 (8)
C110.0280 (8)0.0433 (10)0.0321 (8)0.0044 (7)0.0036 (7)−0.0003 (8)
C120.0269 (8)0.0330 (8)0.0288 (8)0.0038 (7)0.0050 (6)0.0027 (7)
C130.0315 (9)0.0335 (8)0.0306 (8)0.0042 (7)0.0076 (7)0.0037 (7)
C140.0253 (9)0.0500 (11)0.0496 (11)0.0033 (8)0.0027 (8)−0.0003 (9)
C150.0304 (9)0.0412 (10)0.0409 (9)0.0008 (8)0.0006 (7)−0.0029 (8)

Geometric parameters (Å, °)

Ni1—O12.0476 (13)N6—C81.332 (3)
Ni1—O32.0526 (13)N6—H610.853 (10)
Ni1—O52.0567 (13)N6—H620.849 (10)
Ni1—N72.0561 (14)N7—C121.326 (2)
Ni1—N42.0805 (14)N7—C151.340 (2)
Ni1—N12.0857 (15)N8—C141.329 (3)
O1—C11.267 (2)N8—C131.356 (2)
O2—C11.252 (2)N9—C131.329 (2)
O3—C61.274 (2)N9—H910.860 (10)
O4—C61.237 (2)N9—H920.848 (10)
O5—C111.276 (2)N10—H1010.861 (9)
O6—C111.237 (2)N10—H1020.861 (9)
O1W—H1W10.84 (1)N10—H1030.853 (9)
O1W—H1W20.85 (1)N10—H1040.844 (9)
O2W—H2W10.85 (1)C1—C21.503 (3)
O2W—H2W20.84 (1)C2—C31.423 (3)
O3W—H3W10.85 (1)C4—C51.375 (3)
O3W—H3W20.86 (1)C4—H40.9300
N1—C21.332 (2)C5—H50.9300
N1—C51.345 (3)C6—C71.498 (3)
N2—C41.332 (3)C7—C81.421 (2)
N2—C31.344 (3)C9—C101.374 (3)
N3—C31.339 (3)C9—H90.9300
N3—H310.854 (10)C10—H100.9300
N3—H320.858 (10)C11—C121.511 (2)
N4—C71.335 (2)C12—C131.426 (2)
N4—C101.339 (2)C14—C151.377 (3)
N5—C91.326 (3)C14—H140.9300
N5—C81.347 (3)C15—H150.9300
O1—Ni1—O393.69 (6)H103—N10—H104111.9 (14)
O1—Ni1—O5169.25 (5)O2—C1—O1125.01 (18)
O3—Ni1—O594.48 (6)O2—C1—C2118.53 (16)
O1—Ni1—N793.74 (6)O1—C1—C2116.43 (16)
O3—Ni1—N786.83 (5)N1—C2—C3120.28 (17)
O5—Ni1—N779.76 (5)N1—C2—C1115.18 (16)
O1—Ni1—N493.66 (6)C3—C2—C1124.54 (17)
O3—Ni1—N479.14 (5)N3—C3—N2118.03 (19)
O5—Ni1—N494.73 (6)N3—C3—C2121.75 (19)
N7—Ni1—N4164.51 (6)N2—C3—C2120.16 (18)
O1—Ni1—N179.56 (6)N2—C4—C5123.1 (2)
O3—Ni1—N1170.67 (6)N2—C4—H4118.5
O5—Ni1—N193.05 (6)C5—C4—H4118.5
N7—Ni1—N199.95 (6)N1—C5—C4119.79 (19)
N4—Ni1—N194.76 (6)N1—C5—H5120.1
C1—O1—Ni1115.52 (12)C4—C5—H5120.1
C6—O3—Ni1116.28 (12)O4—C6—O3124.70 (18)
C11—O5—Ni1115.38 (11)O4—C6—C7119.59 (17)
H1W1—O1W—H1W2111 (2)O3—C6—C7115.71 (16)
H2W1—O2W—H2W2111 (2)N4—C7—C8120.49 (17)
H3W1—O3W—H3W2108 (2)N4—C7—C6115.85 (15)
C2—N1—C5119.07 (16)C8—C7—C6123.65 (17)
C2—N1—Ni1111.95 (12)N6—C8—N5117.76 (17)
C5—N1—Ni1127.91 (13)N6—C8—C7122.34 (18)
C4—N2—C3117.56 (18)N5—C8—C7119.90 (17)
C3—N3—H31117.1 (19)N5—C9—C10123.55 (18)
C3—N3—H32118 (2)N5—C9—H9118.2
H31—N3—H32124 (3)C10—C9—H9118.2
C7—N4—C10119.01 (15)N4—C10—C9119.64 (18)
C7—N4—Ni1112.91 (12)N4—C10—H10120.2
C10—N4—Ni1128.06 (13)C9—C10—H10120.2
C9—N5—C8117.40 (16)O6—C11—O5125.35 (17)
C8—N6—H61114.4 (17)O6—C11—C12119.08 (16)
C8—N6—H62120.9 (18)O5—C11—C12115.57 (16)
H61—N6—H62125 (2)N7—C12—C13120.69 (15)
C12—N7—C15119.61 (15)N7—C12—C11115.47 (15)
C12—N7—Ni1113.37 (11)C13—C12—C11123.71 (16)
C15—N7—Ni1125.84 (12)N9—C13—N8117.77 (16)
C14—N8—C13117.41 (16)N9—C13—C12122.88 (16)
C13—N9—H91116.9 (18)N8—C13—C12119.35 (16)
C13—N9—H92120.5 (17)N8—C14—C15123.63 (17)
H91—N9—H92121 (2)N8—C14—H14118.2
H101—N10—H102107.1 (13)C15—C14—H14118.2
H101—N10—H103108.6 (14)N7—C15—C14119.21 (17)
H102—N10—H103108.8 (13)N7—C15—H15120.4
H101—N10—H104110.0 (13)C14—C15—H15120.4
H102—N10—H104110.3 (14)
O3—Ni1—O1—C1170.89 (13)O1—C1—C2—C3−167.48 (17)
O5—Ni1—O1—C1−49.7 (3)C4—N2—C3—N3177.4 (2)
N7—Ni1—O1—C1−102.05 (13)C4—N2—C3—C20.1 (3)
N4—Ni1—O1—C191.56 (13)N1—C2—C3—N3−175.23 (18)
N1—Ni1—O1—C1−2.61 (13)C1—C2—C3—N33.6 (3)
O1—Ni1—O3—C6−96.17 (15)N1—C2—C3—N22.0 (3)
O5—Ni1—O3—C690.82 (15)C1—C2—C3—N2−179.12 (17)
N7—Ni1—O3—C6170.28 (15)C3—N2—C4—C5−1.0 (3)
N4—Ni1—O3—C6−3.15 (14)C2—N1—C5—C42.1 (3)
O1—Ni1—O5—C11−53.7 (3)Ni1—N1—C5—C4−164.99 (16)
O3—Ni1—O5—C1185.68 (13)N2—C4—C5—N10.0 (4)
N7—Ni1—O5—C11−0.27 (13)Ni1—O3—C6—O4−177.33 (18)
N4—Ni1—O5—C11165.13 (13)Ni1—O3—C6—C73.5 (2)
N1—Ni1—O5—C11−99.84 (13)C10—N4—C7—C8−0.6 (3)
O1—Ni1—N1—C28.76 (12)Ni1—N4—C7—C8178.20 (13)
O5—Ni1—N1—C2−179.11 (12)C10—N4—C7—C6−179.78 (17)
N7—Ni1—N1—C2100.76 (12)Ni1—N4—C7—C6−1.0 (2)
N4—Ni1—N1—C2−84.10 (13)O4—C6—C7—N4179.16 (19)
O1—Ni1—N1—C5176.63 (17)O3—C6—C7—N4−1.6 (3)
O5—Ni1—N1—C5−11.24 (17)O4—C6—C7—C80.0 (3)
N7—Ni1—N1—C5−91.37 (17)O3—C6—C7—C8179.19 (17)
N4—Ni1—N1—C583.77 (17)C9—N5—C8—N6178.60 (19)
O1—Ni1—N4—C795.17 (13)C9—N5—C8—C7−1.0 (3)
O3—Ni1—N4—C72.10 (12)N4—C7—C8—N6−178.67 (19)
O5—Ni1—N4—C7−91.56 (13)C6—C7—C8—N60.5 (3)
N7—Ni1—N4—C7−23.2 (3)N4—C7—C8—N50.9 (3)
N1—Ni1—N4—C7174.97 (12)C6—C7—C8—N5−179.97 (17)
O1—Ni1—N4—C10−86.20 (16)C8—N5—C9—C100.8 (3)
O3—Ni1—N4—C10−179.26 (17)C7—N4—C10—C90.4 (3)
O5—Ni1—N4—C1087.08 (16)Ni1—N4—C10—C9−178.17 (14)
N7—Ni1—N4—C10155.4 (2)N5—C9—C10—N4−0.5 (3)
N1—Ni1—N4—C10−6.39 (17)Ni1—O5—C11—O6177.70 (16)
O1—Ni1—N7—C12175.68 (12)Ni1—O5—C11—C12−3.4 (2)
O3—Ni1—N7—C12−90.82 (12)C15—N7—C12—C130.5 (2)
O5—Ni1—N7—C124.31 (12)Ni1—N7—C12—C13168.81 (12)
N4—Ni1—N7—C12−65.9 (3)C15—N7—C12—C11−175.57 (16)
N1—Ni1—N7—C1295.64 (12)Ni1—N7—C12—C11−7.23 (18)
O1—Ni1—N7—C15−16.83 (15)O6—C11—C12—N7−173.77 (17)
O3—Ni1—N7—C1576.67 (15)O5—C11—C12—N77.2 (2)
O5—Ni1—N7—C15171.80 (16)O6—C11—C12—C1310.3 (3)
N4—Ni1—N7—C15101.6 (2)O5—C11—C12—C13−168.66 (16)
N1—Ni1—N7—C15−96.87 (15)C14—N8—C13—N9−177.44 (18)
Ni1—O1—C1—O2174.82 (15)C14—N8—C13—C122.5 (3)
Ni1—O1—C1—C2−3.5 (2)N7—C12—C13—N9177.08 (17)
C5—N1—C2—C3−3.1 (3)C11—C12—C13—N9−7.2 (3)
Ni1—N1—C2—C3166.01 (13)N7—C12—C13—N8−2.9 (2)
C5—N1—C2—C1177.96 (16)C11—C12—C13—N8172.81 (16)
Ni1—N1—C2—C1−12.97 (18)C13—N8—C14—C150.1 (3)
O2—C1—C2—N1−166.99 (16)C12—N7—C15—C142.1 (3)
O1—C1—C2—N111.5 (2)Ni1—N7—C15—C14−164.65 (14)
O2—C1—C2—C314.1 (3)N8—C14—C15—N7−2.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H31···O20.85 (1)2.08 (2)2.740 (3)134 (2)
N6—H61···O40.85 (1)2.01 (2)2.701 (3)138 (2)
N6—H62···N5i0.85 (1)2.15 (1)2.992 (2)175 (2)
N9—H91···O60.86 (1)2.07 (2)2.733 (2)134 (2)
N9—H92···O3ii0.85 (1)2.10 (1)2.924 (2)164 (2)
N10—H101···O20.86 (1)1.91 (1)2.756 (3)169 (3)
N10—H102···O1w0.86 (1)1.94 (1)2.779 (3)164 (3)
N10—H103···O2w0.85 (1)2.07 (1)2.919 (3)172 (3)
N10—H104···N8iii0.84 (1)2.36 (2)3.018 (3)135 (2)
O1w—H1w1···O10.84 (1)2.25 (2)2.964 (3)143 (4)
O1w—H1w2···N2iv0.85 (1)2.00 (1)2.842 (3)171 (4)
O2w—H2w1···O5v0.85 (1)2.03 (1)2.869 (2)168 (3)
O2w—H2w2···O6vi0.84 (1)1.96 (1)2.766 (2)159 (3)
O3w—H3w1···O40.85 (1)2.39 (5)2.812 (3)111 (4)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) x+1/2, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5228).

References

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  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
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