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In the complexes [Ni(cyclam)(OCOR)2] (cyclam = 1,4,8,11-tetraazacyclotetradecane), where (RCOO) is 2-naphtho-ate [bis-(2-naphthoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (I), monoclinic P21/c, Z′ = 0.5], 3,5-dinitrobenzoate [bis-(3,5-dinitrobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (II), triclinic P\bar 1, Z′ = 0.5], 4-nitrobenzoate [bis-(4-nitrobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (III), monoclinic P21/n, Z′ = 0.5], 3-hydroxybenzoate [bis-(3-hydroxybenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (IV), monoclinic P21/c, Z′ = 0.5] and 4-aminobenzo-ate [bis-(4-aminobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II), (V), monoclinic C2/c, Z′ = 0.5], the Ni lies on a centre of inversion with monodentate carboxylato ligands occupying trans sites. Compound (I) consists of isolated molecules. In (II) and (III), N—H...O hydrogen bonds link the complexes into chains. Compounds (IV) and (III) form two- and three-dimensional structures generated entirely by hard hydrogen bonds. The 5-hydroxyisophthalate(2−) anion forms a hydrated complex, [Ni(cyclam)(5-hydroxyisophthalate)(H2O)]·4H2O {[aqua-(5-hydroxyisophthalato)-1,4,8,11-tetraazacyclotetradecanenickel(II)] tetrahydrate, (VI), monoclinic Cc, Z′ = 1}, in which the monodentate carboxylato ligand and a water molecule occupy trans sites at Ni: extensive hydrogen bonding links the molecular aggregates into a three-dimensional framework. The terephthalate(2−) anion forms a hydrated linear coordination polymer {catena-poly[terephthalato-1,4,8,11-tetraazacyclotetradecanenickel(II)] monohydrate, (VII), monoclinic C2/c, Z′ = 0.5}. In 1,2,4,5-benzenecarboxylate tris[1,4,8,11-tetraazacyclotetradecanenickel(II)] diperchlorate hydrate (VIII), [Ni(cyclam)]3·[1,2,4,5-benzenetetracarboxylate(4−)]·[ClO4]2·-[H2O]3, there are two distinct Ni sites: [Ni(cyclam)]2+ and centrosymmetric [C10H2O8]4− units form a two-dimensional coordination polymer, whose sheets are linked by centrosymmetric [Ni(cyclam)(H2O)2]2+ cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810101850X/na0129sup1.cif
Contains datablocks global, I, II, III, IV, V, VI, VII, VIII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129IIIsup4.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129IVsup5.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129Vsup6.hkl
Contains datablock V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129VIsup7.hkl
Contains datablock VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129VIIsup8.hkl
Contains datablock VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101850X/na0129VIIIsup9.hkl
Contains datablock VIII

CCDC references: 180182; 180183; 180184; 180185; 180186; 180187; 180188; 180189

Computing details top

Data collection: Kappa-CCD server software (Nonius, 1997) for (I), (II), (IV), (V), (VI), (VII), (VIII); Kappa-CCD server softare (Nonius, 1997) for (III). For all compounds, cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b). Molecular graphics: PLATON (Spek, 20001) for (I); PLATON (Spek, 2001) for (II), (III), (IV), (V), (VI), (VII), (VIII). For all compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 1997b) and PRPKAPPA (Ferguson, 1999).

(I) Bis-(2-naphthoato)-1,4,8,11-tetraazacyclotetradecanenickel(II) top
Crystal data top
C32H38N4NiO4F(000) = 636
Mr = 601.37Dx = 1.366 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.4970 (4) ÅCell parameters from 3144 reflections
b = 10.6563 (4) Åθ = 2.6–27.5°
c = 11.9407 (4) ŵ = 0.71 mm1
β = 92.2080 (17)°T = 150 K
V = 1461.83 (9) Å3Block, purple
Z = 20.36 × 0.26 × 0.18 mm
Data collection top
Kappa-CCD
diffractometer
3328 independent reflections
Radiation source: fine-focus sealed X-ray tube2895 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 014
Tmin = 0.785, Tmax = 0.883k = 013
9394 measured reflectionsl = 1515
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.077H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0155P)2 + 0.7435P]
where P = (Fo2 + 2Fc2)/3
3328 reflections(Δ/σ)max = 0.001
187 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.37 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.01919 (9)
O10.39898 (9)0.34617 (10)0.54652 (8)0.0268 (2)
O20.39786 (11)0.22396 (11)0.39435 (10)0.0384 (3)
C110.24257 (12)0.19082 (13)0.64991 (12)0.0217 (3)
C120.27874 (12)0.16666 (13)0.54398 (12)0.0210 (3)
C130.23432 (13)0.06007 (14)0.48509 (13)0.0270 (3)
C140.15576 (14)0.01766 (15)0.53301 (14)0.0308 (3)
C150.11721 (13)0.00529 (14)0.64248 (14)0.0275 (3)
C160.03531 (15)0.07267 (17)0.69482 (16)0.0396 (4)
C170.00158 (16)0.0457 (2)0.79955 (17)0.0442 (5)
C180.04227 (15)0.05950 (18)0.85834 (15)0.0383 (4)
C190.12280 (13)0.13622 (15)0.81110 (13)0.0290 (3)
C1100.16119 (12)0.11186 (14)0.70172 (12)0.0232 (3)
C1110.36627 (12)0.25133 (13)0.48961 (12)0.0220 (3)
N10.60752 (11)0.39074 (12)0.40417 (10)0.0245 (3)
C20.71607 (14)0.37508 (17)0.47247 (14)0.0325 (4)
C30.68618 (14)0.35421 (17)0.59425 (14)0.0334 (4)
N40.61582 (11)0.46044 (13)0.63234 (10)0.0263 (3)
C50.56383 (14)0.43833 (16)0.74220 (12)0.0302 (3)
C60.48728 (14)0.54690 (16)0.77773 (12)0.0312 (3)
C70.37303 (14)0.56273 (15)0.71011 (12)0.0286 (3)
H110.27260.26190.68940.026*
H130.25940.04270.41180.032*
H140.12650.08820.49230.037*
H160.00570.14470.65650.048*
H170.05720.09840.83290.053*
H180.01610.07760.93110.046*
H190.15310.20620.85200.035*
H10.57310.31200.39700.029*
H2A0.76520.45090.46640.039*
H2B0.76030.30230.44500.039*
H3A0.64200.27500.60110.040*
H3B0.75860.34740.64150.040*
H40.66540.52900.64080.032*
H5A0.62700.42550.79980.036*
H5B0.51660.36070.73800.036*
H6A0.53240.62560.77240.037*
H6B0.46930.53500.85740.037*
H7A0.33220.48100.70530.034*
H7B0.32260.62260.74910.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.02131 (14)0.01902 (14)0.01737 (13)0.00436 (10)0.00246 (9)0.00057 (9)
O10.0335 (6)0.0237 (5)0.0235 (5)0.0114 (4)0.0066 (4)0.0022 (4)
O20.0501 (7)0.0347 (6)0.0319 (6)0.0172 (5)0.0192 (5)0.0103 (5)
C110.0203 (7)0.0188 (7)0.0259 (7)0.0012 (5)0.0000 (5)0.0024 (5)
C120.0201 (6)0.0180 (6)0.0249 (7)0.0012 (5)0.0001 (5)0.0024 (5)
C130.0299 (8)0.0249 (8)0.0261 (7)0.0042 (6)0.0000 (6)0.0008 (6)
C140.0322 (8)0.0249 (8)0.0350 (8)0.0093 (6)0.0039 (7)0.0004 (6)
C150.0234 (7)0.0249 (8)0.0339 (8)0.0054 (6)0.0016 (6)0.0075 (6)
C160.0348 (9)0.0353 (9)0.0485 (10)0.0150 (7)0.0018 (8)0.0108 (8)
C170.0329 (9)0.0484 (11)0.0519 (11)0.0128 (8)0.0085 (8)0.0194 (9)
C180.0339 (9)0.0443 (10)0.0375 (9)0.0009 (8)0.0124 (7)0.0153 (8)
C190.0265 (7)0.0288 (8)0.0321 (8)0.0027 (6)0.0050 (6)0.0069 (6)
C1100.0186 (6)0.0225 (7)0.0284 (7)0.0008 (5)0.0011 (5)0.0067 (6)
C1110.0237 (7)0.0202 (7)0.0222 (7)0.0026 (6)0.0025 (5)0.0013 (5)
N10.0266 (6)0.0222 (6)0.0250 (6)0.0048 (5)0.0046 (5)0.0000 (5)
C20.0256 (8)0.0372 (9)0.0351 (8)0.0034 (7)0.0054 (6)0.0020 (7)
C30.0293 (8)0.0364 (9)0.0343 (8)0.0038 (7)0.0007 (7)0.0082 (7)
N40.0272 (6)0.0288 (7)0.0228 (6)0.0071 (5)0.0009 (5)0.0035 (5)
C50.0344 (8)0.0354 (9)0.0206 (7)0.0081 (7)0.0009 (6)0.0059 (6)
C60.0393 (9)0.0330 (8)0.0215 (7)0.0115 (7)0.0038 (6)0.0014 (6)
C70.0342 (8)0.0283 (8)0.0239 (7)0.0081 (7)0.0099 (6)0.0039 (6)
Geometric parameters (Å, º) top
Ni1—N4i2.070 (2)C18—H180.95
Ni1—N42.070 (2)C19—C1101.419 (2)
Ni1—N1i2.074 (2)C19—H190.95
Ni1—N12.074 (2)N1—C21.474 (2)
Ni1—O1i2.096 (2)N1—C7i1.477 (2)
Ni1—O12.096 (2)N1—H10.93
O1—C1111.267 (2)C2—C31.523 (2)
O2—C1111.242 (2)C2—H2A0.99
C11—C121.371 (2)C2—H2B0.99
C11—C1101.418 (2)C3—N41.473 (2)
C11—H110.95C3—H3A0.99
C12—C131.420 (2)C3—H3B0.99
C12—C1111.516 (2)N4—C51.481 (2)
C13—C141.367 (2)N4—H40.93
C13—H130.95C5—C61.524 (2)
C14—C151.418 (2)C5—H5A0.99
C14—H140.95C5—H5B0.99
C15—C161.419 (2)C6—C71.524 (2)
C15—C1101.421 (2)C6—H6A0.99
C16—C171.367 (3)C6—H6B0.99
C16—H160.95C7—N1i1.477 (2)
C17—C181.406 (3)C7—H7A0.99
C17—H170.95C7—H7B0.99
C18—C191.373 (2)
N4i—Ni1—N4180.0O2—C111—O1126.0 (12)
N4i—Ni1—N1i85.83 (5)O2—C111—C12118.3 (2)
N4—Ni1—N1i94.17 (5)O1—C111—C12115.7 (2)
N4i—Ni1—N194.17 (5)C2—N1—C7i113.2 (2)
N4—Ni1—N185.83 (5)C2—N1—Ni1105.56 (9)
N1i—Ni1—N1180.0C7i—N1—Ni1115.8 (2)
N4i—Ni1—O1i89.15 (5)C2—N1—H1107.3
N4—Ni1—O1i90.85 (5)C7i—N1—H1107.3
N1i—Ni1—O1i93.17 (4)Ni1—N1—H1107.3
N1—Ni1—O1i86.83 (4)N1—C2—C3109.1 (2)
N4i—Ni1—O190.85 (5)N1—C2—H2A109.9
N4—Ni1—O189.15 (5)C3—C2—H2A109.9
N1i—Ni1—O186.83 (4)N1—C2—H2B109.9
N1—Ni1—O193.17 (4)C3—C2—H2B109.9
O1i—Ni1—O1180.0H2A—C2—H2B108.3
C111—O1—Ni1129.63 (9)N4—C3—C2109.2 (2)
C12—C11—C110121.3 (2)N4—C3—H3A109.8
C12—C11—H11119.3C2—C3—H3A109.8
C110—C11—H11119.3N4—C3—H3B109.8
C11—C12—C13119.4 (2)C2—C3—H3B109.8
C11—C12—C111120.9 (2)H3A—C3—H3B108.3
C13—C12—C111119.7 (2)C3—N4—C5113.4 (2)
C14—C13—C12120.5 (2)C3—N4—Ni1105.41 (9)
C14—C13—H13119.7C5—N4—Ni1116.02 (9)
C12—C13—H13119.7C3—N4—H4107.2
C13—C14—C15121.1 (2)C5—N4—H4107.2
C13—C14—H14119.5Ni1—N4—H4107.2
C15—C14—H14119.5N4—C5—C6112.5 (2)
C14—C15—C16122.8 (2)N4—C5—H5A109.1
C14—C15—C110118.6 (2)C6—C5—H5A109.1
C16—C15—C110118.6 (2)N4—C5—H5B109.1
C17—C16—C15121.0 (2)C6—C5—H5B109.1
C17—C16—H16119.5H5A—C5—H5B107.8
C15—C16—H16119.5C5—C6—C7115.6 (2)
C16—C17—C18120.5 (2)C5—C6—H6A108.4
C16—C17—H17119.8C7—C6—H6A108.4
C18—C17—H17119.8C5—C6—H6B108.4
C19—C18—C17120.3 (2)C7—C6—H6B108.4
C19—C18—H18119.9H6A—C6—H6B107.4
C17—C18—H18119.9N1i—C7—C6111.6 (2)
C18—C19—C110120.5 (2)N1i—C7—H7A109.3
C18—C19—H19119.7C6—C7—H7A109.3
C110—C19—H19119.7N1i—C7—H7B109.3
C11—C110—C19121.8 (2)C6—C7—H7B109.3
C11—C110—C15119.0 (2)H7A—C7—H7B108.0
C19—C110—C15119.2 (2)
N4i—Ni1—O1—C11156.5 (2)C11—C12—C111—O12.5 (2)
N4—Ni1—O1—C111123.5 (2)C13—C12—C111—O1178.1 (2)
N1i—Ni1—O1—C111142.3 (3)N4i—Ni1—N1—C2165.9 (2)
N1—Ni1—O1—C11137.7 (2)N4—Ni1—N1—C214.1 (2)
C110—C11—C12—C130.3 (2)O1i—Ni1—N1—C277.03 (9)
C110—C11—C12—C111179.7 (2)O1—Ni1—N1—C2103.0 (2)
C11—C12—C13—C140.3 (2)N4i—Ni1—N1—C7i39.8 (2)
C111—C12—C13—C14179.7 (2)N4—Ni1—N1—C7i140.2 (2)
C12—C13—C14—C150.4 (2)O1i—Ni1—N1—C7i49.1 (2)
C13—C14—C15—C16179.6 (2)O1—Ni1—N1—C7i130.9 (2)
C13—C14—C15—C1100.5 (2)C7i—N1—C2—C3168.1 (2)
C14—C15—C16—C17178.5 (2)Ni1—N1—C2—C340.4 (2)
C110—C15—C16—C170.6 (3)N1—C2—C3—N456.9 (2)
C15—C16—C17—C180.8 (3)C2—C3—N4—C5169.2 (2)
C16—C17—C18—C190.1 (3)C2—C3—N4—Ni141.3 (2)
C17—C18—C19—C1101.2 (2)N1i—Ni1—N4—C3164.86 (9)
C12—C11—C110—C19179.7 (2)N1—Ni1—N4—C315.14 (9)
C12—C11—C110—C150.4 (2)O1i—Ni1—N4—C3101.90 (9)
C18—C19—C110—C11178.8 (2)O1—Ni1—N4—C378.10 (9)
C18—C19—C110—C151.4 (2)N1i—Ni1—N4—C538.9 (2)
C14—C15—C110—C110.5 (2)N1—Ni1—N4—C5141.4 (2)
C16—C15—C110—C11179.6 (2)O1i—Ni1—N4—C5131.8 (2)
C14—C15—C110—C19179.7 (2)O1—Ni1—N4—C548.2 (2)
C16—C15—C110—C190.5 (2)C3—N4—C5—C6177.6 (2)
Ni1—O1—C111—O27.4 (2)Ni1—N4—C5—C655.4 (2)
Ni1—O1—C111—C12171.29 (9)N4—C5—C6—C770.1 (2)
C11—C12—C111—O2178.6 (2)C5—C6—C7—N1i71.1 (2)
C13—C12—C111—O20.7 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.932.222.994 (2)140
(II) Bis-(3,5-dinitrobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II) top
Crystal data top
C24H30N8NiO12Z = 1
Mr = 681.27F(000) = 354
Triclinic, P1Dx = 1.564 Mg m3
a = 7.7663 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.7845 (6) ÅCell parameters from 5718 reflections
c = 10.4026 (7) Åθ = 2.8–27.2°
α = 99.826 (2)°µ = 0.75 mm1
β = 97.966 (2)°T = 293 K
γ = 108.388 (2)°Plate, colourless
V = 723.30 (7) Å30.30 × 0.24 × 0.02 mm
Data collection top
Kappa-CCD
diffractometer
3135 independent reflections
Radiation source: fine-focus sealed X-ray tube2560 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
φ scans, and ω scans with κ offsetsθmax = 27.2°, θmin = 2.8°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 09
Tmin = 0.807, Tmax = 0.985k = 1211
17662 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.097 w = 1/[σ2(Fo2)P)2 + 0.3293P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
3135 reflectionsΔρmax = 0.29 e Å3
206 parametersΔρmin = 0.43 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.013 (3)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891]which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.03420 (15)
N10.2732 (3)0.5215 (2)0.57420 (19)0.0407 (5)
C20.2156 (4)0.4009 (3)0.6446 (3)0.0529 (7)
C30.2281 (4)0.2618 (3)0.5626 (3)0.0538 (7)
N40.4181 (3)0.2920 (2)0.5391 (2)0.0415 (5)
C50.4378 (4)0.1739 (3)0.4400 (3)0.0469 (6)
C60.6350 (4)0.2085 (3)0.4189 (3)0.0494 (6)
C70.7033 (4)0.3306 (3)0.3461 (3)0.0484 (6)
O110.3435 (2)0.40263 (19)0.30221 (16)0.0456 (4)
O120.1530 (2)0.5311 (2)0.28440 (18)0.0547 (5)
O320.0894 (3)0.0360 (3)0.2587 (2)0.0800 (7)
O310.2989 (3)0.0153 (2)0.0804 (2)0.0681 (6)
O510.3909 (3)0.3286 (3)0.0794 (2)0.0696 (6)
O520.4066 (3)0.1585 (2)0.2464 (2)0.0704 (6)
N30.1675 (4)0.0330 (2)0.1442 (2)0.0537 (6)
N50.3274 (3)0.2430 (3)0.1391 (2)0.0520 (6)
C110.1133 (3)0.3314 (2)0.1059 (2)0.0362 (5)
C120.1873 (3)0.2326 (3)0.0429 (2)0.0402 (5)
C130.0918 (3)0.1419 (3)0.0800 (2)0.0422 (6)
C140.0744 (4)0.1447 (3)0.1438 (2)0.0454 (6)
C150.1450 (3)0.2432 (3)0.0773 (2)0.0406 (5)
C160.0543 (3)0.3368 (3)0.0452 (2)0.0387 (5)
C170.2114 (3)0.4321 (3)0.2431 (2)0.0373 (5)
H10.18020.50110.50240.049*
H2A0.08940.38390.65630.063*
H2B0.29580.42770.73190.063*
H3A0.19730.18280.60970.065*
H3B0.14060.23070.47810.065*
H40.49120.29830.61780.050*
H5A0.35600.16010.35580.056*
H5B0.39990.08200.46940.056*
H6A0.64510.11890.36930.059*
H6B0.71720.23550.50540.059*
H7A0.82110.33160.32440.058*
H7B0.61560.30980.26310.058*
H120.29930.22760.08290.048*
H140.13590.08360.22720.055*
H160.10490.40260.08650.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0336 (2)0.0363 (2)0.0305 (2)0.01418 (18)0.00215 (16)0.00157 (16)
N10.0408 (11)0.0437 (11)0.0369 (11)0.0181 (9)0.0050 (8)0.0031 (9)
C20.0536 (15)0.0572 (16)0.0560 (16)0.0230 (13)0.0247 (13)0.0161 (13)
C30.0516 (15)0.0466 (15)0.0645 (18)0.0142 (12)0.0205 (13)0.0148 (13)
N40.0432 (11)0.0433 (11)0.0371 (11)0.0181 (9)0.0043 (9)0.0045 (9)
C50.0559 (15)0.0361 (13)0.0458 (14)0.0180 (11)0.0060 (12)0.0017 (11)
C60.0545 (15)0.0464 (14)0.0495 (15)0.0274 (12)0.0077 (12)0.0009 (12)
C70.0502 (14)0.0512 (15)0.0445 (14)0.0244 (12)0.0112 (11)0.0014 (11)
O110.0459 (10)0.0510 (10)0.0361 (9)0.0235 (8)0.0060 (7)0.0013 (8)
O120.0540 (11)0.0602 (12)0.0452 (10)0.0309 (9)0.0064 (8)0.0082 (9)
O320.0983 (17)0.0786 (15)0.0522 (13)0.0348 (13)0.0104 (12)0.0174 (11)
O310.0765 (15)0.0683 (14)0.0687 (14)0.0402 (12)0.0159 (12)0.0097 (11)
O510.0534 (12)0.0792 (15)0.0716 (14)0.0291 (11)0.0048 (10)0.0081 (12)
O520.0660 (13)0.0622 (13)0.0571 (13)0.0111 (10)0.0284 (10)0.0001 (10)
N30.0663 (15)0.0442 (13)0.0481 (14)0.0169 (11)0.0188 (12)0.0028 (10)
N50.0462 (12)0.0511 (13)0.0490 (13)0.0116 (11)0.0077 (10)0.0104 (11)
C110.0376 (12)0.0355 (12)0.0307 (11)0.0090 (9)0.0014 (9)0.0064 (9)
C120.0413 (13)0.0410 (13)0.0363 (12)0.0142 (10)0.0036 (10)0.0070 (10)
C130.0503 (14)0.0383 (13)0.0363 (13)0.0149 (11)0.0091 (11)0.0043 (10)
C140.0537 (15)0.0414 (14)0.0310 (12)0.0088 (11)0.0000 (11)0.0035 (10)
C150.0385 (12)0.0406 (13)0.0352 (12)0.0074 (10)0.0032 (10)0.0100 (10)
C160.0402 (12)0.0383 (12)0.0348 (12)0.0130 (10)0.0031 (10)0.0065 (10)
C170.0338 (11)0.0399 (12)0.0332 (12)0.0119 (10)0.0005 (9)0.0019 (10)
Geometric parameters (Å, º) top
Ni1—N12.073 (2)C6—H6B0.97
Ni1—N1i2.073 (2)C7—N1i1.482 (3)
Ni1—N42.062 (2)C7—H7A0.97
Ni1—N4i2.062 (2)C7—H7B0.97
Ni1—O11i2.127 (2)O11—C171.259 (3)
Ni1—O112.127 (2)O12—C171.233 (3)
N1—C21.477 (3)O31—N31.214 (3)
N1—C7i1.482 (3)O32—N31.229 (3)
N1—H10.91O51—N51.224 (3)
C2—C31.516 (4)O52—N51.218 (3)
C2—H2A0.97N3—C131.479 (3)
C2—H2B0.97N5—C151.472 (3)
C3—N41.474 (3)C11—C121.391 (3)
C3—H3A0.97C11—C161.386 (3)
C3—H3B0.97C11—C171.527 (3)
N4—C51.473 (3)C12—C131.381 (3)
N4—H40.91C12—H120.93
C5—C61.516 (4)C13—C141.377 (4)
C5—H5A0.97C14—C151.386 (4)
C5—H5B0.97C14—H140.93
C6—C71.517 (4)C15—C161.380 (3)
C6—H6A0.97C16—H160.93
N4—Ni1—N4i180.0C6—C5—H5B109.1
N4—Ni1—N185.46 (8)H5A—C5—H5B107.9
N4i—Ni1—N194.54 (8)C5—C6—C7116.2 (2)
N4—Ni1—N1i94.54 (8)C5—C6—H6A108.2
N4i—Ni1—N1i85.46 (8)C7—C6—H6A108.2
N1—Ni1—N1i180.0C5—C6—H6B108.2
N4—Ni1—O11i91.86 (7)C7—C6—H6B108.2
N4i—Ni1—O11i88.14 (7)H6A—C6—H6B107.4
N1—Ni1—O11i86.49 (7)N1i—C7—C6112.6 (2)
N1i—Ni1—O11i93.51 (7)N1i—C7—H7A109.1
N4—Ni1—O1188.14 (7)C6—C7—H7A109.1
N4i—Ni1—O1191.86 (7)N1i—C7—H7B109.1
N1—Ni1—O1193.51 (7)C6—C7—H7B109.1
N1i—Ni1—O1186.49 (7)H7A—C7—H7B107.8
O11i—Ni1—O11180C17—O11—Ni1127.9 (2)
C2—N1—C7i114.0 (2)O31—N3—O32124.4 (3)
C2—N1—Ni1105.8 (2)O31—N3—C13118.5 (2)
C7i—N1—Ni1116.7 (2)O32—N3—C13117.0 (3)
C2—N1—H1106.6O52—N5—O51123.7 (2)
C7i—N1—H1106.6O52—N5—C15118.5 (2)
Ni1—N1—H1106.6O51—N5—C15117.9 (2)
N1—C2—C3108.7 (2)C16—C11—C12119.8 (2)
N1—C2—H2A109.9C16—C11—C17119.2 (2)
C3—C2—H2A109.9C12—C11—C17121.0 (2)
N1—C2—H2B109.9C13—C12—C11118.9 (2)
C3—C2—H2B109.9C13—C12—H12120.6
H2A—C2—H2B108.3C11—C12—H12120.6
N4—C3—C2109.3 (2)C14—C13—C12123.0 (2)
N4—C3—H3A109.8C14—C13—N3118.3 (2)
C2—C3—H3A109.8C12—C13—N3118.6 (2)
N4—C3—H3B109.8C13—C14—C15116.5 (2)
C2—C3—H3B109.8C13—C14—H14121.8
H3A—C3—H3B108.3C15—C14—H14121.8
C5—N4—C3113.9 (2)C16—C15—C14122.8 (2)
C5—N4—Ni1115.8 (2)C16—C15—N5119.3 (2)
C3—N4—Ni1106.1 (2)C14—C15—N5117.9 (2)
C5—N4—H4106.8C15—C16—C11119.1 (2)
C3—N4—H4106.8C15—C16—H16120.5
Ni1—N4—H4106.8C11—C16—H16120.5
N4—C5—C6112.4 (2)O12—C17—O11127.2 (2)
N4—C5—H5A109.1O12—C17—C11117.4 (2)
C6—C5—H5A109.1O11—C17—C11115.4 (2)
N4—C5—H5B109.1
N4—Ni1—N1—C215.0 (2)N1i—Ni1—O11—C17144.0 (2)
N4i—Ni1—N1—C2165.0 (2)C16—C11—C12—C130.4 (3)
O11i—Ni1—N1—C277.1 (2)C17—C11—C12—C13178.8 (2)
O11—Ni1—N1—C2102.9 (2)C11—C12—C13—C140.0 (4)
N4—Ni1—N1—C7i143.0 (2)C11—C12—C13—N3177.7 (2)
N4i—Ni1—N1—C7i37.0 (2)O31—N3—C13—C14169.6 (2)
O11i—Ni1—N1—C7i50.9 (2)O32—N3—C13—C149.0 (3)
O11—Ni1—N1—C7i129.2 (2)O31—N3—C13—C128.2 (3)
C7i—N1—C2—C3170.5 (2)O32—N3—C13—C12173.2 (2)
Ni1—N1—C2—C341.0 (2)C12—C13—C14—C150.9 (4)
N1—C2—C3—N456.4 (3)N3—C13—C14—C15176.9 (2)
C2—C3—N4—C5169.1 (2)C13—C14—C15—C161.3 (4)
C2—C3—N4—Ni140.5 (2)C13—C14—C15—N5176.6 (2)
N1—Ni1—N4—C5141.5 (12)O52—N5—C15—C16179.1 (2)
N1i—Ni1—N4—C538.5 (2)O51—N5—C15—C161.0 (3)
O11i—Ni1—N4—C5132.1 (2)O52—N5—C15—C141.1 (3)
O11—Ni1—N4—C547.9 (2)O51—N5—C15—C14179.0 (2)
N1—Ni1—N4—C314.1 (2)C14—C15—C16—C110.9 (4)
N1i—Ni1—N4—C3165.9 (2)N5—C15—C16—C11177.0 (2)
O11i—Ni1—N4—C3100.4 (2)C12—C11—C16—C150.0 (3)
O11—Ni1—N4—C379.6 (2)C17—C11—C16—C15178.4 (2)
C3—N4—C5—C6179.8 (2)Ni1—O11—C17—O125.5 (4)
Ni1—N4—C5—C656.8 (3)Ni1—O11—C17—C11173.8 (2)
N4—C5—C6—C771.0 (3)C16—C11—C17—O1211.8 (3)
C5—C6—C7—N1i68.7 (3)C12—C11—C17—O12169.8 (2)
N4—Ni1—O11—C17121.4 (2)C16—C11—C17—O11167.5 (2)
N4i—Ni1—O11—C1758.6 (2)C12—C11—C17—O1110.9 (3)
N1—Ni1—O11—C1736.0 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O120.912.333.056 (3)137
N4—H4···O52ii0.912.353.132 (3)144
C2—H2A···O12iii0.972.403.287 (4)152
Symmetry codes: (ii) x+1, y, z+1; (iii) x, y+1, z+1.
(III) Bis-(4-nitrobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II) top
Crystal data top
C24H32N6NiO8F(000) = 620
Mr = 591.27Dx = 1.555 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.8106 (3) ÅCell parameters from 2781 reflections
b = 8.4187 (2) Åθ = 2.9–27.8°
c = 12.8397 (4) ŵ = 0.83 mm1
β = 114.2543 (10)°T = 150 K
V = 1262.51 (6) Å3Block, colourless
Z = 20.26 × 0.24 × 0.22 mm
Data collection top
Kappa-CCD
diffractometer
2894 independent reflections
Radiation source: fine-focus sealed X-ray tube2456 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ scans, and ω scans with κ offsetsθmax = 27.8°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 016
Tmin = 0.813, Tmax = 0.838k = 010
8828 measured reflectionsl = 1615
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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0314P)2 + 0.5307P]
where P = (Fo2 + 2Fc2)/3
2894 reflections(Δ/σ)max = 0.001
178 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.39 e Å3
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.01595 (11)
N10.57282 (10)0.33040 (15)0.62464 (11)0.0193 (3)
C20.62427 (13)0.21138 (19)0.57574 (14)0.0228 (3)
C30.54312 (13)0.18189 (19)0.45225 (14)0.0226 (3)
N40.52317 (10)0.33495 (16)0.39076 (11)0.0195 (3)
C50.43331 (14)0.3272 (2)0.27367 (14)0.0238 (3)
C60.40728 (14)0.48956 (19)0.21559 (14)0.0236 (3)
C70.34781 (13)0.6063 (2)0.26408 (13)0.0217 (3)
O110.33036 (9)0.42120 (13)0.46359 (10)0.0218 (3)
O120.34942 (10)0.22940 (17)0.59137 (12)0.0410 (4)
O410.23591 (12)0.2008 (2)0.40490 (17)0.0595 (5)
O420.25454 (10)0.41423 (19)0.30553 (12)0.0423 (4)
N140.19596 (12)0.3093 (2)0.36853 (14)0.0343 (4)
C110.16301 (13)0.32350 (19)0.47697 (13)0.0195 (3)
C120.09284 (14)0.4217 (2)0.38919 (14)0.0239 (3)
C130.02574 (14)0.4187 (2)0.35172 (15)0.0262 (4)
C140.07089 (13)0.3137 (2)0.40536 (14)0.0250 (4)
C150.00398 (14)0.2141 (2)0.49259 (15)0.0271 (4)
C160.11389 (14)0.2198 (2)0.52871 (14)0.0245 (4)
C170.29251 (13)0.32381 (19)0.51547 (14)0.0210 (3)
H10.51350.28050.63590.023*
H2A0.63780.11120.61970.027*
H2B0.69870.25060.57980.027*
H3A0.57710.10430.41710.027*
H3B0.46980.13820.44820.027*
H40.59100.36150.38480.023*
H5A0.36250.28360.27600.029*
H5B0.45800.25380.22790.029*
H6A0.48010.53760.22170.028*
H6B0.35840.47400.13340.028*
H7A0.31590.69520.20980.026*
H7B0.28340.55210.27300.026*
H120.12640.49230.35400.029*
H130.07370.48610.29180.031*
H150.03800.14310.52720.032*
H160.16140.15270.58900.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01204 (15)0.01563 (16)0.01780 (16)0.00064 (10)0.00373 (11)0.00118 (10)
N10.0137 (6)0.0196 (6)0.0219 (7)0.0007 (5)0.0046 (5)0.0025 (5)
C20.0186 (7)0.0188 (8)0.0283 (9)0.0026 (6)0.0068 (6)0.0035 (7)
C30.0206 (7)0.0172 (8)0.0285 (9)0.0003 (6)0.0085 (7)0.0004 (6)
N40.0139 (6)0.0207 (6)0.0219 (7)0.0022 (5)0.0054 (5)0.0004 (5)
C50.0219 (8)0.0263 (8)0.0208 (8)0.0036 (7)0.0063 (6)0.0036 (7)
C60.0206 (8)0.0294 (9)0.0190 (8)0.0025 (7)0.0062 (6)0.0013 (7)
C70.0161 (7)0.0273 (8)0.0180 (8)0.0023 (6)0.0031 (6)0.0033 (6)
O110.0147 (5)0.0245 (6)0.0244 (6)0.0033 (4)0.0062 (4)0.0030 (5)
O120.0183 (6)0.0473 (8)0.0505 (9)0.0006 (6)0.0071 (6)0.0282 (7)
O410.0273 (7)0.0675 (11)0.0894 (13)0.0090 (7)0.0297 (8)0.0087 (10)
O420.0186 (6)0.0622 (10)0.0403 (8)0.0062 (6)0.0061 (6)0.0062 (7)
N140.0184 (7)0.0482 (10)0.0376 (9)0.0038 (7)0.0128 (7)0.0118 (8)
C110.0167 (7)0.0206 (8)0.0208 (8)0.0021 (6)0.0073 (6)0.0028 (6)
C120.0193 (8)0.0258 (9)0.0267 (9)0.0018 (6)0.0094 (6)0.0008 (7)
C130.0197 (8)0.0313 (10)0.0253 (9)0.0021 (7)0.0068 (6)0.0015 (7)
C140.0148 (7)0.0332 (9)0.0280 (9)0.0030 (6)0.0097 (6)0.0103 (7)
C150.0239 (8)0.0316 (9)0.0312 (9)0.0054 (7)0.0169 (7)0.0025 (7)
C160.0222 (8)0.0276 (9)0.0245 (8)0.0025 (7)0.0104 (7)0.0004 (7)
C170.0168 (7)0.0214 (8)0.0239 (8)0.0029 (6)0.0073 (6)0.0003 (6)
Geometric parameters (Å, º) top
Ni1—N1i2.060 (2)C6—H6A0.99
Ni1—N12.060 (2)C6—H6B0.99
Ni1—N4i2.080 (2)C7—N1i1.472 (2)
Ni1—N42.080 (2)C7—H7A0.99
Ni1—O11i2.132 (2)C7—H7B0.99
Ni1—O112.132 (2)O11—C171.271 (2)
N1—C7i1.472 (2)O12—C171.237 (2)
N1—C21.474 (2)O41—N141.229 (2)
N1—H10.93O42—N141.224 (2)
C2—C31.517 (2)N14—C141.473 (2)
C2—H2A0.99C11—C121.389 (2)
C2—H2B0.99C11—C161.394 (2)
C3—N41.478 (2)C11—C171.524 (2)
C3—H3A0.99C12—C131.393 (2)
C3—H3B0.99C12—H120.95
N4—C51.472 (2)C13—C141.385 (2)
N4—H40.93C13—H130.95
C5—C61.527 (2)C14—C151.380 (3)
C5—H5A0.99C15—C161.386 (2)
C5—H5B0.99C15—H150.95
C6—C71.524 (2)C16—H160.95
N1i—Ni1—N1180.0C6—C5—H5A109.1
N1i—Ni1—N4i85.20 (5)N4—C5—H5B109.1
N1—Ni1—N4i94.80 (5)C6—C5—H5B109.1
N1i—Ni1—N494.80 (5)H5A—C5—H5B107.9
N1—Ni1—N485.20 (5)C7—C6—C5115.04 (13)
N4i—Ni1—N4180.0C7—C6—H6A108.5
N1i—Ni1—O11i92.88 (5)C5—C6—H6A108.5
N1—Ni1—O11i87.12 (5)C7—C6—H6B108.5
N4i—Ni1—O11i93.39 (5)C5—C6—H6B108.5
N4—Ni1—O11i86.61 (5)H6A—C6—H6B107.5
N1i—Ni1—O1187.12 (5)N1i—C7—C6111.6 (2)
N1—Ni1—O1192.88 (5)N1i—C7—H7A109.3
N4i—Ni1—O1186.61 (5)C6—C7—H7A109.3
N4—Ni1—O1193.39 (5)N1i—C7—H7B109.3
O11i—Ni1—O11180.0C6—C7—H7B109.3
C7i—N1—C2114.1 (2)H7A—C7—H7B108.0
C7i—N1—Ni1114.5 (2)C17—O11—Ni1131.3 (2)
C2—N1—Ni1106.2 (2)O42—N14—O41123.3 (2)
C7i—N1—H1107.2O42—N14—C14119.0 (2)
C2—N1—H1107.2O41—N14—C14117.7 (2)
Ni1—N1—H1107.2C12—C11—C16119.4 (2)
N1—C2—C3108.8 (2)C12—C11—C17121.2 (2)
N1—C2—H2A109.9C16—C11—C17119.4 (2)
C3—C2—H2A109.9C11—C12—C13121.3 (2)
N1—C2—H2B109.9C11—C12—H12119.3
C3—C2—H2B109.9C13—C12—H12119.3
H2A—C2—H2B108.3C14—C13—C12117.3 (2)
N4—C3—C2108.0 (2)C14—C13—H13121.3
N4—C3—H3A110.1C12—C13—H13121.3
C2—C3—H3A110.1C15—C14—C13123.0 (2)
N4—C3—H3B110.1C15—C14—N14118.5 (2)
C2—C3—H3B110.1C13—C14—N14118.5 (2)
H3A—C3—H3B108.4C14—C15—C16118.6 (2)
C5—N4—C3113.5 (2)C14—C15—H15120.7
C5—N4—Ni1116.7 (2)C16—C15—H15120.7
C3—N4—Ni1105.28 (9)C15—C16—C11120.4 (2)
C5—N4—H4106.9C15—C16—H16119.8
C3—N4—H4106.9C11—C16—H16119.8
Ni1—N4—H4106.9O12—C17—O11126.8 (2)
N4—C5—C6112.4 (2)O12—C17—C11117.7 (2)
N4—C5—H5A109.1O11—C17—C11115.5 (2)
N4i—Ni1—N1—C7i39.6 (12)N1i—Ni1—O11—C17169.7 (2)
N4—Ni1—N1—C7i140.4 (2)N1—Ni1—O11—C1710.3 (12)
O11i—Ni1—N1—C7i53.5 (2)N4i—Ni1—O11—C1784.3 (2)
O11—Ni1—N1—C7i126.5 (2)N4—Ni1—O11—C1795.7 (2)
N4i—Ni1—N1—C2166.51 (9)C16—C11—C12—C130.0 (2)
N4—Ni1—N1—C213.49 (9)C17—C11—C12—C13178.3 (2)
O11i—Ni1—N1—C273.34 (9)C11—C12—C13—C140.1 (2)
O11—Ni1—N1—C2106.66 (9)C12—C13—C14—C150.0 (3)
C7i—N1—C2—C3168.2 (2)C12—C13—C14—N14179.2 (2)
Ni1—N1—C2—C341.1 (2)O42—N14—C14—C15167.8 (2)
N1—C2—C3—N458.2 (11)O41—N14—C14—C1510.9 (2)
C2—C3—N4—C5172.0 (2)O42—N14—C14—C1311.5 (2)
C2—C3—N4—Ni143.2 (2)O41—N14—C14—C13169.8 (2)
N1i—Ni1—N4—C536.6 (2)C13—C14—C15—C160.3 (3)
N1—Ni1—N4—C5143.4 (2)N14—C14—C15—C16178.9 (2)
O11i—Ni1—N4—C5129.2 (2)C14—C15—C16—C110.5 (3)
O11—Ni1—N4—C550.8 (2)C12—C11—C16—C150.3 (2)
N1i—Ni1—N4—C3163.41 (9)C17—C11—C16—C15178.0 (2)
N1—Ni1—N4—C316.59 (9)Ni1—O11—C17—O1213.3 (3)
O11i—Ni1—N4—C3103.98 (9)Ni1—O11—C17—C11167.9 (2)
O11—Ni1—N4—C376.02 (9)C12—C11—C17—O12177.5 (2)
C3—N4—C5—C6175.1 (2)C16—C11—C17—O120.8 (2)
Ni1—N4—C5—C652.5 (2)C12—C11—C17—O111.4 (2)
N4—C5—C6—C769.4 (2)C16—C11—C17—O11179.6 (2)
C5—C6—C7—N1i74.1 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O120.931.992.845 (2)153
N4—H4···O41ii0.932.523.221 (2)132
C16—H16···O42iii0.952.603.439 (2)148
Symmetry codes: (ii) x+1, y, z; (iii) x+1/2, y+1/2, z+1/2.
(IV) Bis-(3-hydroxybenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II) top
Crystal data top
C24H34N4NiO6F(000) = 564
Mr = 533.26Dx = 1.485 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.5180 (3) ÅCell parameters from 2748 reflections
b = 13.2496 (5) Åθ = 2.9–27.5°
c = 10.7720 (4) ŵ = 0.86 mm1
β = 101.161 (2)°T = 150 K
V = 1192.74 (8) Å3Needle, colourless
Z = 20.40 × 0.28 × 0.22 mm
Data collection top
Kappa-CCD
diffractometer
2721 independent reflections
Radiation source: fine-focus sealed X-ray tube2194 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 011
Tmin = 0.724, Tmax = 0.833k = 017
9996 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.076 w = 1/[σ2(Fo2) + (0.0232P)2 + 0.6219P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2721 reflectionsΔρmax = 0.33 e Å3
162 parametersΔρmin = 0.36 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0036 (10)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.01498 (11)
N10.43833 (18)0.62473 (11)0.38455 (13)0.0188 (3)
C20.3062 (2)0.59176 (15)0.28307 (18)0.0254 (4)
C30.3435 (2)0.48667 (14)0.24034 (17)0.0255 (4)
N40.36826 (19)0.41851 (11)0.35181 (14)0.0205 (3)
C50.4336 (2)0.31855 (14)0.32804 (18)0.0249 (4)
C60.4585 (2)0.25182 (14)0.44562 (18)0.0267 (4)
C70.5968 (2)0.28196 (13)0.55099 (18)0.0236 (4)
O110.71243 (15)0.47431 (9)0.43020 (12)0.0211 (3)
O120.74555 (16)0.60133 (9)0.30107 (13)0.0256 (3)
O131.07609 (17)0.20467 (10)0.32970 (12)0.0275 (3)
C110.8565 (2)0.44052 (13)0.26869 (16)0.0184 (4)
C120.9286 (2)0.35489 (14)0.32983 (17)0.0200 (4)
C131.0080 (2)0.28633 (14)0.26516 (17)0.0197 (4)
C141.0144 (2)0.30365 (14)0.13851 (17)0.0219 (4)
C150.9400 (2)0.38830 (14)0.07732 (17)0.0226 (4)
C160.8619 (2)0.45748 (14)0.14164 (17)0.0213 (4)
C170.7665 (2)0.51106 (13)0.33895 (16)0.0180 (4)
H10.52520.63870.34660.023*
H2A0.29420.63930.21090.030*
H2B0.20460.59080.31480.030*
H3A0.25370.46180.17500.031*
H3B0.44110.48840.20330.031*
H40.26820.40730.37170.025*
H5A0.53710.32760.30060.030*
H5B0.35910.28460.25860.030*
H6A0.35880.25230.48000.032*
H6B0.47640.18170.41990.032*
H7A0.61870.22650.61360.028*
H7B0.69410.29230.51500.028*
H31.12460.17060.28310.041*
H120.92370.34310.41600.024*
H141.06950.25780.09420.026*
H150.94230.39910.00950.027*
H160.81270.51570.09940.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01602 (17)0.01348 (17)0.01663 (16)0.00086 (13)0.00607 (11)0.00009 (12)
N10.0184 (8)0.0183 (8)0.0217 (8)0.0016 (6)0.0087 (6)0.0025 (6)
C20.0224 (10)0.0275 (10)0.0253 (10)0.0009 (8)0.0022 (8)0.0063 (8)
C30.0260 (10)0.0296 (11)0.0199 (9)0.0043 (8)0.0017 (7)0.0000 (8)
N40.0206 (8)0.0194 (8)0.0227 (8)0.0019 (6)0.0067 (6)0.0013 (6)
C50.0306 (11)0.0195 (10)0.0261 (10)0.0043 (8)0.0096 (8)0.0086 (8)
C60.0346 (11)0.0166 (9)0.0317 (11)0.0015 (8)0.0134 (9)0.0034 (8)
C70.0285 (10)0.0161 (9)0.0292 (10)0.0081 (8)0.0127 (8)0.0041 (7)
O110.0215 (7)0.0213 (7)0.0235 (6)0.0037 (5)0.0121 (5)0.0048 (5)
O120.0286 (7)0.0158 (6)0.0372 (8)0.0029 (6)0.0181 (6)0.0042 (6)
O130.0321 (8)0.0241 (7)0.0294 (7)0.0091 (6)0.0137 (6)0.0024 (6)
C110.0175 (9)0.0175 (9)0.0216 (9)0.0023 (7)0.0072 (7)0.0002 (7)
C120.0203 (9)0.0205 (9)0.0208 (9)0.0001 (7)0.0082 (7)0.0016 (7)
C130.0183 (9)0.0164 (8)0.0254 (9)0.0010 (7)0.0067 (7)0.0004 (7)
C140.0215 (9)0.0219 (9)0.0237 (9)0.0030 (8)0.0080 (7)0.0063 (8)
C150.0244 (10)0.0250 (10)0.0194 (9)0.0026 (8)0.0070 (7)0.0011 (7)
C160.0221 (9)0.0188 (9)0.0238 (9)0.0010 (8)0.0062 (7)0.0024 (7)
C170.0164 (8)0.0176 (9)0.0207 (8)0.0000 (7)0.0054 (7)0.0006 (7)
Geometric parameters (Å, º) top
Ni1—N42.069 (2)C6—H6A0.99
Ni1—N4i2.069 (2)C6—H6B0.99
Ni1—N12.074 (2)C7—N1i1.477 (2)
Ni1—N1i2.074 (2)C7—H7A0.99
Ni1—O11i2.117 (2)C7—H7B0.99
Ni1—O112.117 (2)O11—C171.261 (2)
N1—C21.475 (2)O12—C171.265 (2)
N1—C7i1.477 (2)O13—C131.354 (2)
N1—H10.93O13—H30.84
C2—C31.519 (3)C11—C121.393 (3)
C2—H2A0.99C11—C161.396 (2)
C2—H2B0.99C11—C171.503 (2)
C3—N41.485 (2)C12—C131.397 (2)
C3—H3A0.99C12—H120.95
C3—H3B0.99C13—C141.395 (2)
N4—C51.478 (2)C14—C151.390 (3)
N4—H40.93C14—H140.95
C5—C61.525 (3)C15—C161.393 (3)
C5—H5A0.99C15—H150.95
C5—H5B0.99C16—H160.95
C6—C71.523 (3)
N4—Ni1—N4i180.0N4—C5—H5A109.2
N4—Ni1—N185.22 (6)C6—C5—H5A109.2
N4i—Ni1—N194.78 (6)N4—C5—H5B109.2
N4—Ni1—N1i94.78 (6)C6—C5—H5B109.2
N4i—Ni1—N1i85.22 (6)H5A—C5—H5B107.9
N1—Ni1—N1i180.0C7—C6—C5115.5 (2)
N4—Ni1—O11i89.12 (6)C7—C6—H6A108.4
N4i—Ni1—O11i90.88 (6)C5—C6—H6A108.4
N1—Ni1—O11i87.14 (5)C7—C6—H6B108.4
N1i—Ni1—O11i92.86 (5)C5—C6—H6B108.4
N4—Ni1—O1190.88 (6)H6A—C6—H6B107.5
N4i—Ni1—O1189.12 (6)N1i—C7—C6111.8 (2)
N1—Ni1—O1192.86 (5)N1i—C7—H7A109.2
N1i—Ni1—O1187.14 (5)C6—C7—H7A109.2
O11i—Ni1—O11180.0N1i—C7—H7B109.2
C2—N1—C7i113.7 (2)C6—C7—H7B109.2
C2—N1—Ni1106.1 (2)H7A—C7—H7B107.9
C7i—N1—Ni1115.9 (2)C17—O11—Ni1132.9 (2)
C2—N1—H1106.9C13—O13—H3109.5
C7i—N1—H1106.9C12—C11—C16120.0 (2)
Ni1—N1—H1106.9C12—C11—C17119.3 (2)
N1—C2—C3108.8 (2)C16—C11—C17120.7 (12)
N1—C2—H2A109.9C11—C12—C13120.4 (2)
C3—C2—H2A109.9C11—C12—H12119.8
N1—C2—H2B109.9C13—C12—H12119.8
C3—C2—H2B109.9O13—C13—C14122.7 (2)
H2A—C2—H2B108.3O13—C13—C12117.7 (2)
N4—C3—C2108.5 (2)C14—C13—C12119.7 (2)
N4—C3—H3A110.0C15—C14—C13119.7 (2)
C2—C3—H3A110.0C15—C14—H14120.1
N4—C3—H3B110.0C13—C14—H14120.1
C2—C3—H3B110.0C14—C15—C16120.9 (2)
H3A—C3—H3B108.4C14—C15—H15119.6
C5—N4—C3113.9 (2)C16—C15—H15119.6
C5—N4—Ni1115.8 (2)C15—C16—C11119.4 (2)
C3—N4—Ni1106.1 (2)C15—C16—H16120.3
C5—N4—H4106.9C11—C16—H16120.3
C3—N4—H4106.9O11—C17—O12124.5 (2)
Ni1—N4—H4106.9O11—C17—C11116.8 (2)
N4—C5—C6111.8 (2)O12—C17—C11118.6 (2)
N4—Ni1—N1—C214.9 (2)N4—C5—C6—C771.9 (2)
N4i—Ni1—N1—C2165.1 (2)C5—C6—C7—N1i71.7 (2)
O11i—Ni1—N1—C274.4 (2)N4—Ni1—O11—C1775.4 (2)
O11—Ni1—N1—C2105.6 (2)N4i—Ni1—O11—C17104.6 (2)
N4—Ni1—N1—C7i142.1 (2)N1—Ni1—O11—C179.9 (2)
N4i—Ni1—N1—C7i38.0 (2)N1i—Ni1—O11—C17170.1 (2)
O11i—Ni1—N1—C7i52.7 (2)C16—C11—C12—C130.8 (3)
O11—Ni1—N1—C7i127.3 (2)C17—C11—C12—C13177.7 (2)
C7i—N1—C2—C3167.0 (2)C11—C12—C13—O13179.8 (2)
Ni1—N1—C2—C341.5 (2)C11—C12—C13—C140.3 (3)
N1—C2—C3—N456.9 (2)O13—C13—C14—C15179.1 (2)
C2—C3—N4—C5169.7 (2)C12—C13—C14—C150.8 (3)
C2—C3—N4—Ni141.1 (2)C13—C14—C15—C161.5 (3)
N1—Ni1—N4—C5142.0 (2)C14—C15—C16—C111.0 (3)
N1i—Ni1—N4—C538.0 (2)C12—C11—C16—C150.1 (3)
O11i—Ni1—N4—C5130.832)C17—C11—C16—C15177.0 (2)
O11—Ni1—N4—C549.2 (2)Ni1—O11—C17—O1234.1 (3)
N1—Ni1—N4—C314.6 (2)Ni1—O11—C17—C11143.6 (2)
N1i—Ni1—N4—C3165.4 (2)C12—C11—C17—O1124.2 (2)
O11i—Ni1—N4—C3101.8 (2)C16—C11—C17—O11152.7 (2)
O11—Ni1—N4—C378.2 (2)C12—C11—C17—O12157.9 (2)
C3—N4—C5—C6179.4 (2)C16—C11—C17—O1225.1 (3)
Ni1—N4—C5—C656.0 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O120.932.092.943 (2)152
O13—H3···O12ii0.841.812.645 (2)172
Symmetry code: (ii) x+2, y1/2, z+1/2.
(V) Bis-(4-aminobenzoato)-1,4,8,11-tetraazacyclotetradecanenickel(II) top
Crystal data top
C24H36N6NiO4F(000) = 1128
Mr = 531.30Dx = 1.420 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 18.4430 (4) ÅCell parameters from 2913 reflections
b = 8.4149 (2) Åθ = 2.8–27.5°
c = 16.8262 (4) ŵ = 0.82 mm1
β = 107.8774 (14)°T = 150 K
V = 2485.27 (10) Å3Block, colourless
Z = 40.42 × 0.40 × 0.38 mm
Data collection top
Kappa-CCD
diffractometer
2823 independent reflections
Radiation source: fine-focus sealed X-ray tube2395 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 023
Tmin = 0.724, Tmax = 0.745k = 010
12342 measured reflectionsl = 2120
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0282P)2 + 2.6861P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2823 reflectionsΔρmax = 0.32 e Å3
161 parametersΔρmin = 0.34 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (3)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.50000.01544 (10)
N10.55981 (7)0.42978 (16)0.42106 (8)0.0203 (3)
C20.50599 (10)0.3387 (2)0.35408 (10)0.0266 (4)
C30.45702 (11)0.2348 (2)0.39085 (11)0.0294 (4)
N40.41827 (8)0.33600 (16)0.43749 (8)0.0238 (3)
C50.38198 (10)0.2450 (2)0.49033 (12)0.0316 (4)
C60.34463 (10)0.3531 (2)0.53936 (12)0.0323 (4)
C70.39919 (10)0.4466 (2)0.60996 (11)0.0270 (4)
O110.55427 (6)0.32521 (13)0.58986 (7)0.0219 (2)
O120.64821 (6)0.21858 (14)0.54774 (7)0.0231 (3)
N140.69692 (8)0.14447 (18)0.89459 (9)0.0283 (3)
C110.63534 (8)0.13716 (17)0.67784 (9)0.0165 (3)
C120.59138 (9)0.13522 (18)0.73217 (9)0.0186 (3)
C130.61119 (9)0.04265 (19)0.80356 (10)0.0206 (3)
C140.67787 (9)0.04965 (19)0.82489 (10)0.0201 (3)
C150.72308 (9)0.0451 (2)0.77074 (10)0.0224 (3)
C160.70153 (9)0.04533 (19)0.69872 (10)0.0201 (3)
C170.61086 (8)0.23363 (18)0.59906 (9)0.0170 (3)
H10.59640.35800.45090.024*
H2A0.53430.27140.32550.032*
H2B0.47320.41230.31250.032*
H3A0.41870.17780.34560.035*
H3B0.48930.15500.42890.035*
H40.38000.39160.39840.029*
H5A0.42100.17840.52990.038*
H5B0.34290.17320.45450.038*
H6A0.31120.42930.49990.039*
H6B0.31180.28710.56300.039*
H7A0.37020.49700.64390.032*
H7B0.43660.37270.64650.032*
H14A0.66720.14810.92670.034*
H14B0.73890.20170.90720.034*
H120.54680.19900.71980.022*
H130.57940.04150.83850.025*
H150.76890.10500.78400.027*
H160.73240.04500.66270.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01769 (15)0.01486 (15)0.01392 (14)0.00007 (10)0.00506 (10)0.00034 (10)
N10.0242 (7)0.0204 (7)0.0174 (6)0.0045 (5)0.0080 (5)0.0032 (5)
C20.0369 (10)0.0260 (9)0.0164 (7)0.0046 (7)0.0074 (7)0.0014 (6)
C30.0401 (10)0.0217 (8)0.0235 (8)0.0040 (7)0.0056 (7)0.0069 (7)
N40.0257 (7)0.0216 (7)0.0216 (7)0.0041 (5)0.0036 (6)0.0004 (5)
C50.0318 (9)0.0281 (9)0.0341 (9)0.0107 (7)0.0090 (8)0.0034 (8)
C60.0232 (8)0.0365 (10)0.0382 (10)0.0031 (7)0.0110 (7)0.0109 (8)
C70.0266 (8)0.0328 (9)0.0264 (8)0.0052 (7)0.0152 (7)0.0088 (7)
O110.0231 (6)0.0230 (6)0.0207 (5)0.0071 (4)0.0083 (4)0.0062 (4)
O120.0229 (6)0.0303 (6)0.0183 (5)0.0043 (5)0.0098 (4)0.0039 (5)
N140.0264 (7)0.0360 (8)0.0248 (7)0.0096 (6)0.0113 (6)0.0143 (6)
C110.0174 (7)0.0156 (7)0.0163 (7)0.0017 (5)0.0047 (6)0.0010 (6)
C120.0191 (7)0.0176 (7)0.0199 (7)0.0019 (6)0.0070 (6)0.0009 (6)
C130.0229 (8)0.0221 (8)0.0192 (7)0.0007 (6)0.0100 (6)0.0001 (6)
C140.0218 (8)0.0187 (7)0.0191 (7)0.0005 (6)0.0053 (6)0.0021 (6)
C150.0186 (7)0.0245 (8)0.0243 (8)0.0048 (6)0.0069 (6)0.0052 (6)
C160.0187 (7)0.0223 (8)0.0215 (8)0.0002 (6)0.0093 (6)0.0014 (6)
C170.0173 (7)0.0159 (7)0.0166 (7)0.0016 (6)0.0034 (5)0.0005 (6)
Geometric parameters (Å, º) top
Ni1—N1i2.057 (2)C6—H6A0.99
Ni1—N12.057 (2)C6—H6B0.99
Ni1—N4i2.076 (2)C7—N1i1.473 (2)
Ni1—N42.076 (2)C7—H7A0.99
Ni1—O11i2.127 (2)C7—H7B0.99
Ni1—O112.127 (2)O11—C171.268 (2)
N1—C21.468 (2)O12—C171.266 (2)
N1—C7i1.473 (2)N14—C141.372 (2)
N1—H10.93N14—H14A0.88
C2—C31.518 (2)N14—H14B0.88
C2—H2A0.99C11—C161.395 (2)
C2—H2B0.99C11—C121.396 (2)
C3—N41.482 (2)C11—C171.501 (2)
C3—H3A0.99C12—C131.383 (2)
C3—H3B0.99C12—H120.95
N4—C51.480 (2)C13—C141.405 (2)
N4—H40.93C13—H130.95
C5—C61.527 (3)C14—C151.412 (2)
C5—H5A0.99C15—C161.382 (2)
C5—H5B0.99C15—H150.95
C6—C71.519 (3)C16—H160.95
N1i—Ni1—N1180.0C6—C5—H5A109.2
N1i—Ni1—N4i86.08 (5)N4—C5—H5B109.2
N1—Ni1—N4i93.92 (5)C6—C5—H5B109.2
N1i—Ni1—N493.92 (5)H5A—C5—H5B107.9
N1—Ni1—N486.08 (5)C7—C6—C5115.5 (2)
N4i—Ni1—N4180.0C7—C6—H6A108.4
N1i—Ni1—O11i91.83 (5)C5—C6—H6A108.4
N1—Ni1—O11i88.18 (5)C7—C6—H6B108.4
N4i—Ni1—O11i90.60 (5)C5—C6—H6B108.4
N4—Ni1—O11i89.40 (5)H6A—C6—H6B107.5
N1i—Ni1—O1188.18 (5)N1i—C7—C6112.2 (2)
N1—Ni1—O1191.82 (5)N1i—C7—H7A109.2
N4i—Ni1—O1189.40 (5)C6—C7—H7A109.2
N4—Ni1—O1190.60 (5)N1i—C7—H7B109.2
O11i—Ni1—O11180.0C6—C7—H7B109.2
C2—N1—C7i113.4 (2)H7A—C7—H7B107.9
C2—N1—Ni1106.0 (2)C17—O11—Ni1134.2 (2)
C7i—N1—Ni1117.5 (2)C14—N14—H14A120.0
C2—N1—H1106.4C14—N14—H14B120.0
C7i—N1—H1106.4H14A—N14—H14B120.0
Ni1—N1—H1106.4C16—C11—C12117.9 (12)
N1—C2—C3109.5 (2)C16—C11—C17121.7 (2)
N1—C2—H2A109.8C12—C11—C17120.45 (2)
C3—C2—H2A109.8C13—C12—C11121.6 (2)
N1—C2—H2B109.8C13—C12—H12119.2
C3—C2—H2B109.8C11—C12—H12119.2
H2A—C2—H2B108.2C12—C13—C14120.7 (2)
N4—C3—C2109.2 (2)C12—C13—H13119.7
N4—C3—H3A109.8C14—C13—H13119.7
C2—C3—H3A109.8N14—C14—C13120.9 (2)
N4—C3—H3B109.8N14—C14—C15121.4 (2)
C2—C3—H3B109.8C13—C14—C15117.7 (2)
H3A—C3—H3B108.3C16—C15—C14120.9 (2)
C5—N4—C3113.7 (2)C16—C15—H15119.6
C5—N4—Ni1115.6 (2)C14—C15—H15119.6
C3—N4—Ni1104.9 (2)C15—C16—C11121.3 (2)
C5—N4—H4107.4C15—C16—H16119.3
C3—N4—H4107.4C11—C16—H16119.3
Ni1—N4—H4107.4O12—C17—O11125.3 (2)
N4—C5—C6112.2 (2)O12—C17—C11118.0 (2)
N4—C5—H5A109.2O11—C17—C11116.7 (2)
N4i—Ni1—N1—C2166.3 (2)N4—C5—C6—C770.8 (2)
N4—Ni1—N1—C213.7 (2)C5—C6—C7—N1i69.0 (2)
O11i—Ni1—N1—C275.8 (2)N1i—Ni1—O11—C17168.7 (2)
O11—Ni1—N1—C2104.2 (2)N1—Ni1—O11—C1711.4 (2)
N4i—Ni1—N1—C7i38.4 (2)N4i—Ni1—O11—C1782.6 (2)
N4—Ni1—N1—C7i141.6 (2)N4—Ni1—O11—C1797.5 (2)
O11i—Ni1—N1—C7i52.1 (2)C16—C11—C12—C131.6 (2)
O11—Ni1—N1—C7i127.9 (2)C17—C11—C12—C13177.5 (2)
C7i—N1—C2—C3170.3 (2)C11—C12—C13—C141.8 (2)
Ni1—N1—C2—C340.0 (2)C12—C13—C14—N14178.5 (2)
N1—C2—C3—N456.3 (2)C12—C13—C14—C150.5 (2)
C2—C3—N4—C5168.0 (2)N14—C14—C15—C16177.1 (2)
C2—C3—N4—Ni140.8 (2)C13—C14—C15—C161.0 (2)
N1i—Ni1—N4—C539.0 (2)C14—C15—C16—C111.1 (3)
N1—Ni1—N4—C5141.1 (1)C12—C11—C16—C150.1 (2)
O11i—Ni1—N4—C5130.7 (2)C17—C11—C16—C15179.0 (2)
O11—Ni1—N4—C549.3 (2)Ni1—O11—C17—O125.3 (2)
N1i—Ni1—N4—C3164.9 (2)Ni1—O11—C17—C11174.1 (2)
N1—Ni1—N4—C315.1 (2)C16—C11—C17—O126.3 (2)
O11i—Ni1—N4—C3103.3 (2)C12—C11—C17—O12172.8 (2)
O11—Ni1—N4—C376.7 (2)C16—C11—C17—O11173.1 (2)
C3—N4—C5—C6178.3 (2)C12—C11—C17—O117.8 (2)
Ni1—N4—C5—C657.0 (2)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O120.932.002.868 (2)155
N14—H14A···O12ii0.882.253.043 (2)150
N14—H14B···O12iii0.882.102.954 (2)165
Symmetry codes: (ii) x, y, z+1/2; (iii) x+3/2, y1/2, z+3/2.
(VI) [Aqua-(5-hydroxyisophthalato)-1,4,8,11- tetraazacyclotetradecanenickel(II)] tetrahydrate top
Crystal data top
C18H30N4NiO6·4(H2O)F(000) = 1128
Mr = 529.23Dx = 1.474 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
a = 18.4057 (8) ÅCell parameters from 2739 reflections
b = 9.6927 (4) Åθ = 2.8–27.5°
c = 13.4648 (5) ŵ = 0.87 mm1
β = 96.724 (2)°T = 150 K
V = 2385.61 (17) Å3Plate, purple
Z = 40.36 × 0.34 × 0.04 mm
Data collection top
Kappa-CCD
diffractometer
5106 independent reflections
Radiation source: fine-focus sealed X-ray tube4757 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 2323
Tmin = 0.744, Tmax = 0.966k = 1212
9912 measured reflectionsl = 1717
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2)P)2 + 2.7841P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.082(Δ/σ)max = 0.009
S = 1.03Δρmax = 0.35 e Å3
5106 reflectionsΔρmin = 0.36 e Å3
342 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
12 restraintsExtinction coefficient: 0.0014 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 2357 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.434 (11)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.500367 (18)0.19694 (3)0.50001 (2)0.01553 (9)
N10.51041 (13)0.0522 (2)0.38875 (16)0.0181 (5)
C20.57352 (16)0.0933 (4)0.3380 (2)0.0239 (6)
C30.57334 (16)0.2497 (4)0.3287 (2)0.0221 (6)
N40.57657 (13)0.3102 (2)0.43020 (16)0.0204 (5)
C50.56531 (18)0.4616 (3)0.4298 (2)0.0267 (6)
C60.56375 (18)0.5197 (3)0.5343 (2)0.0279 (6)
C70.49540 (17)0.4861 (3)0.5834 (2)0.0240 (6)
N80.49288 (13)0.3398 (2)0.61357 (16)0.0192 (5)
C90.42410 (18)0.3013 (3)0.6536 (2)0.0243 (7)
C100.42015 (17)0.1450 (4)0.6640 (2)0.0248 (7)
N110.42452 (13)0.0827 (2)0.56478 (16)0.0187 (5)
C120.43508 (17)0.0686 (3)0.5693 (2)0.0249 (6)
C130.44081 (17)0.1301 (3)0.4667 (2)0.0240 (6)
C140.51042 (16)0.0937 (3)0.4208 (2)0.0226 (6)
O10.41696 (11)0.3069 (2)0.41743 (13)0.0200 (4)
O20.37648 (11)0.1701 (2)0.28844 (14)0.0227 (4)
O30.25257 (12)0.7176 (2)0.47024 (14)0.0234 (4)
O40.24784 (12)0.8581 (2)0.34041 (14)0.0239 (4)
O50.22645 (11)0.5052 (2)0.05556 (13)0.0194 (4)
C210.33005 (14)0.3993 (3)0.29374 (19)0.0173 (5)
C220.31571 (15)0.5105 (3)0.35362 (18)0.0169 (5)
C230.27343 (14)0.6215 (3)0.31330 (18)0.0156 (5)
C240.24506 (15)0.6192 (3)0.2125 (2)0.0171 (5)
C250.25802 (14)0.5062 (3)0.15356 (18)0.0151 (5)
C260.30025 (14)0.3959 (3)0.19354 (18)0.0164 (5)
C270.37760 (15)0.2817 (3)0.33636 (18)0.0168 (5)
C280.25685 (14)0.7408 (3)0.37872 (18)0.0164 (5)
O60.58776 (11)0.0983 (2)0.59862 (14)0.0214 (4)
O70.63580 (12)0.2779 (2)0.74172 (16)0.0275 (5)
O80.67775 (13)0.2377 (2)0.93999 (15)0.0287 (5)
O90.76311 (12)0.4569 (2)1.00127 (16)0.0254 (4)
O100.75061 (12)0.5538 (2)1.19632 (14)0.0247 (4)
H10.46940.06300.34210.022*
H2A0.57010.05060.27080.029*
H2B0.61950.06200.37700.029*
H3A0.61610.28040.29620.027*
H3B0.52830.28060.28720.027*
H40.62270.29220.46360.025*
H5A0.51850.48360.38880.032*
H5B0.60520.50660.39840.032*
H6C0.56870.62120.53110.034*
H6D0.60690.48410.57760.034*
H7C0.49410.54530.64310.029*
H7D0.45160.50740.53600.029*
H80.53150.32410.66330.023*
H9C0.38170.33460.60790.029*
H9D0.42240.34520.71970.029*
H10C0.46120.11180.71220.030*
H10D0.37360.11850.68900.030*
H110.37960.09830.52720.022*
H12A0.39340.11160.59800.030*
H12B0.48020.08990.61410.030*
H13A0.39820.09890.42050.029*
H13B0.43770.23180.47180.029*
H14A0.55350.11080.47060.027*
H14B0.51460.15410.36250.027*
H50.24040.43500.02650.029*
H220.33470.51130.42230.020*
H240.21690.69480.18430.020*
H260.30870.31890.15290.020*
H6A0.609 (2)0.143 (4)0.653 (3)0.052 (13)*
H6B0.6248 (18)0.050 (4)0.577 (3)0.040 (11)*
H7A0.641 (2)0.259 (4)0.804 (2)0.038 (11)*
H7B0.670 (2)0.334 (4)0.722 (3)0.040 (11)*
H8A0.710 (2)0.301 (4)0.960 (3)0.050 (13)*
H8B0.697 (3)0.163 (4)0.968 (4)0.068 (15)*
H9A0.758 (2)0.489 (4)1.059 (2)0.035 (10)*
H9B0.758 (2)0.520 (3)0.954 (2)0.030 (10)*
H10A0.7918 (17)0.602 (3)1.222 (2)0.026 (8)*
H10B0.752 (4)0.489 (5)1.240 (4)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01649 (15)0.01509 (14)0.01473 (14)0.00102 (14)0.00067 (10)0.00032 (14)
N10.0179 (11)0.0185 (12)0.0174 (10)0.0016 (9)0.0008 (8)0.0020 (9)
C20.0197 (14)0.0314 (17)0.0206 (13)0.0033 (13)0.0029 (11)0.0047 (12)
C30.0221 (15)0.0310 (18)0.0138 (13)0.0012 (14)0.0049 (11)0.0006 (12)
N40.0203 (12)0.0200 (12)0.0207 (11)0.0014 (10)0.0011 (9)0.0013 (9)
C50.0324 (17)0.0196 (15)0.0278 (15)0.0018 (13)0.0025 (12)0.0042 (11)
C60.0303 (16)0.0212 (15)0.0312 (15)0.0039 (13)0.0011 (12)0.0016 (12)
C70.0285 (16)0.0176 (14)0.0249 (14)0.0008 (12)0.0012 (11)0.0039 (11)
N80.0187 (11)0.0195 (12)0.0188 (11)0.0027 (9)0.0006 (9)0.0015 (9)
C90.0240 (15)0.0294 (18)0.0202 (14)0.0042 (13)0.0055 (11)0.0042 (12)
C100.0236 (15)0.0304 (18)0.0219 (14)0.0018 (14)0.0084 (11)0.0021 (13)
N110.0191 (11)0.0182 (11)0.0184 (10)0.0001 (10)0.0005 (8)0.0020 (9)
C120.0271 (15)0.0189 (14)0.0288 (14)0.0017 (12)0.0034 (12)0.0064 (11)
C130.0272 (15)0.0155 (13)0.0282 (14)0.0011 (12)0.0016 (12)0.0001 (11)
C140.0256 (15)0.0170 (13)0.0246 (13)0.0068 (12)0.0008 (11)0.0045 (10)
O10.0212 (10)0.0193 (10)0.0182 (9)0.0048 (8)0.0033 (7)0.0008 (7)
O20.0263 (11)0.0176 (10)0.0225 (9)0.0052 (8)0.0042 (8)0.0041 (7)
O30.0386 (12)0.0173 (10)0.0150 (9)0.0015 (9)0.0063 (8)0.0002 (7)
O40.0375 (12)0.0139 (9)0.0206 (9)0.0014 (9)0.0042 (8)0.0013 (8)
O50.0260 (10)0.0182 (10)0.0132 (8)0.0029 (8)0.0005 (7)0.0003 (7)
C210.0152 (12)0.0197 (13)0.0165 (12)0.0000 (10)0.0002 (9)0.0019 (10)
C220.0193 (12)0.0173 (13)0.0132 (11)0.0002 (10)0.0013 (9)0.0014 (9)
C230.0166 (12)0.0131 (12)0.0175 (12)0.0006 (10)0.0042 (10)0.0008 (9)
C240.0205 (13)0.0122 (12)0.0181 (12)0.0003 (10)0.0006 (10)0.0020 (9)
C250.0159 (12)0.0166 (12)0.0130 (11)0.0015 (10)0.0022 (9)0.0021 (9)
C260.0181 (12)0.0175 (12)0.0135 (11)0.0014 (10)0.0017 (9)0.0004 (9)
C270.0163 (12)0.0205 (14)0.0138 (11)0.0006 (10)0.0021 (9)0.0012 (9)
C280.0183 (13)0.0142 (12)0.0167 (11)0.0017 (10)0.0022 (9)0.0003 (9)
O60.0209 (10)0.0246 (11)0.0175 (9)0.0040 (9)0.0023 (7)0.0010 (8)
O70.0246 (11)0.0326 (12)0.0236 (11)0.0030 (10)0.0046 (9)0.0012 (9)
O80.0346 (12)0.0190 (11)0.0296 (11)0.0034 (10)0.0081 (9)0.0044 (9)
O90.0323 (12)0.0202 (10)0.0229 (10)0.0020 (9)0.0007 (9)0.0037 (8)
O100.0296 (11)0.0222 (10)0.0214 (10)0.0020 (9)0.0011 (8)0.0043 (8)
Geometric parameters (Å, º) top
Ni1—N112.054 (2)C12—C131.519 (4)
Ni1—N12.077 (2)C12—H12A0.9900
Ni1—N82.079 (2)C12—H12B0.9900
Ni1—O12.081 (2)C13—C141.527 (4)
Ni1—N42.089 (2)C13—H13A0.9900
Ni1—O62.183 (2)C13—H13B0.9900
N1—C21.470 (4)C14—H14A0.9900
N1—C141.479 (4)C14—H14B0.9900
N1—H10.9300O1—C271.261 (3)
C2—C31.521 (5)O2—C271.258 (3)
C2—H2A0.9900O3—C281.264 (3)
C2—H2B0.9900O4—C281.252 (3)
C3—N41.481 (4)O5—C251.378 (3)
C3—H3A0.9900O5—H50.8400
C3—H3B0.9900C21—C221.390 (4)
N4—C51.482 (4)C21—C261.396 (3)
N4—H40.9300C21—C271.509 (4)
C5—C61.520 (4)C22—C231.399 (4)
C5—H5A0.9900C22—H220.9500
C5—H5B0.9900C23—C241.396 (3)
C6—C71.523 (5)C23—C281.507 (4)
C6—H6C0.9900C24—C251.390 (4)
C6—H6D0.9900C24—H240.9500
C7—N81.477 (4)C25—C261.392 (4)
C7—H7C0.9900C26—H260.9500
C7—H7D0.9900O6—H6A0.90 (3)
N8—C91.481 (4)O6—H6B0.90 (3)
N8—H80.9300O7—H7A0.86 (3)
C9—C101.524 (4)O7—H7B0.89 (3)
C9—H9C0.9900O8—H8A0.88 (3)
C9—H9D0.9900O8—H8B0.87 (3)
C10—N111.477 (4)O9—H9A0.85 (3)
C10—H10C0.9900O9—H9B0.88 (3)
C10—H10D0.9900O10—H10A0.92 (3)
N11—C121.480 (4)O10—H10B0.87 (3)
N11—H110.9300
N11—Ni1—N193.70 (9)N8—C9—H9D109.7
N11—Ni1—N886.6 (2)C10—C9—H9D109.7
N1—Ni1—N8178.5 (2)H9C—C9—H9D108.2
N11—Ni1—O190.42 (9)N11—C10—C9108.4 (2)
N1—Ni1—O194.76 (8)N11—C10—H10C110.0
N8—Ni1—O186.77 (8)C9—C10—H10C110.0
N11—Ni1—N4178.34 (9)N11—C10—H10D110.0
N1—Ni1—N484.80 (9)C9—C10—H10D110.0
N8—Ni1—N494.97 (9)H10C—C10—H10D108.4
O1—Ni1—N489.01 (9)C10—N11—C12112.9 (2)
N11—Ni1—O689.69 (8)C10—N11—Ni1106.0 (2)
N1—Ni1—O691.22 (8)C12—N11—Ni1117.3 (2)
N8—Ni1—O687.25 (8)C10—N11—H11106.7
O1—Ni1—O6174.00 (8)C12—N11—H11106.7
N4—Ni1—O691.04 (8)Ni1—N11—H11106.7
C2—N1—C14115.0 (2)N11—C12—C13112.0 (2)
C2—N1—Ni1107.1 (2)N11—C12—H12A109.2
C14—N1—Ni1115.6 (2)C13—C12—H12A109.2
C2—N1—H1106.1N11—C12—H12B109.2
C14—N1—H1106.1C13—C12—H12B109.2
Ni1—N1—H1106.1H12A—C12—H12B107.9
N1—C2—C3108.3 (2)C12—C13—C14115.3 (2)
N1—C2—H2A110.0C12—C13—H13A108.4
C3—C2—H2A110.0C14—C13—H13A108.4
N1—C2—H2B110.0C12—C13—H13B108.4
C3—C2—H2B110.0C14—C13—H13B108.4
H2A—C2—H2B108.4H13A—C13—H13B107.5
N4—C3—C2108.6 (2)N1—C14—C13111.6 (2)
N4—C3—H3A110.0N1—C14—H14A109.3
C2—C3—H3A110.0C13—C14—H14A109.3
N4—C3—H3B110.0N1—C14—H14B109.3
C2—C3—H3B110.0C13—C14—H14B109.3
H3A—C3—H3B108.3H14A—C14—H14B108.0
C3—N4—C5113.4 (2)C27—O1—Ni1132.6 (2)
C3—N4—Ni1104.5 (2)C25—O5—H5109.5
C5—N4—Ni1114.9 (2)C22—C21—C26119.9 (2)
C3—N4—H4107.9C22—C21—C27120.4 (2)
C5—N4—H4107.9C26—C21—C27119.6 (2)
Ni1—N4—H4107.9C21—C22—C23120.4 (2)
N4—C5—C6112.4 (2)C21—C22—H22119.8
N4—C5—H5A109.1C23—C22—H22119.8
C6—C5—H5A109.1C24—C23—C22119.6 (2)
N4—C5—H5B109.1C24—C23—C28120.1 (2)
C6—C5—H5B109.1C22—C23—C28120.3 (2)
H5A—C5—H5B107.9C25—C24—C23119.9 (2)
C5—C6—C7115.4 (3)C25—C24—H24120.1
C5—C6—H6C108.4C23—C24—H24120.1
C7—C6—H6C108.4O5—C25—C24118.1 (2)
C5—C6—H6D108.4O5—C25—C26121.2 (2)
C7—C6—H6D108.4C24—C25—C26120.6 (2)
H6C—C6—H6D107.5C25—C26—C21119.6 (2)
N8—C7—C6112.2 (2)C25—C26—H26120.2
N8—C7—H7C109.2C21—C26—H26120.2
C6—C7—H7C109.2O2—C27—O1125.7 (2)
N8—C7—H7D109.2O2—C27—C21118.7 (2)
C6—C7—H7D109.2O1—C27—C21115.6 (2)
H7C—C7—H7D107.9O4—C28—O3122.9 (2)
C7—N8—C9113.4 (2)O4—C28—C23118.9 (2)
C7—N8—Ni1115.5 (2)O3—C28—C23118.2 (2)
C9—N8—Ni1103.5 (2)Ni1—O6—H6A120 (3)
C7—N8—H8108.0Ni1—O6—H6B124 (2)
C9—N8—H8108.0H6A—O6—H6B103 (4)
Ni1—N8—H8108.0H7A—O7—H7B115 (4)
N8—C9—C10109.6 (2)H8A—O8—H8B103 (4)
N8—C9—H9C109.7H9A—O9—H9B113 (4)
C10—C9—H9C109.7H10A—O10—H10B99 (5)
N11—Ni1—N1—C2169.5 (2)N1—Ni1—N11—C10165.8 (2)
O1—Ni1—N1—C299.8 (2)N8—Ni1—N11—C1012.7 (2)
N4—Ni1—N1—C211.2 (2)O1—Ni1—N11—C1099.4 (2)
O6—Ni1—N1—C279.7 (12)O6—Ni1—N11—C1074.6 (2)
N11—Ni1—N1—C1439.9 (2)N1—Ni1—N11—C1238.7 (2)
O1—Ni1—N1—C14130.6 (2)N8—Ni1—N11—C12139.8 (2)
N4—Ni1—N1—C14140.8 (2)O1—Ni1—N11—C12133.5 (2)
O6—Ni1—N1—C1449.9 (2)O6—Ni1—N11—C1252.5 (2)
C14—N1—C2—C3168.8 (2)C10—N11—C12—C13179.0 (2)
Ni1—N1—C2—C338.9 (2)Ni1—N11—C12—C1355.3 (3)
N1—C2—C3—N458.3 (3)N11—C12—C13—C1469.5 (3)
C2—C3—N4—C5171.2 (2)C2—N1—C14—C13176.3 (2)
C2—C3—N4—Ni145.3 (2)Ni1—N1—C14—C1358.0 (3)
N1—Ni1—N4—C318.8 (2)C12—C13—C14—N171.6 (3)
N8—Ni1—N4—C3162.7 (2)N11—Ni1—O1—C2782.8 (3)
O1—Ni1—N4—C376.1 (2)N1—Ni1—O1—C2710.9 (3)
O6—Ni1—N4—C3110.0 (2)N8—Ni1—O1—C27169.4 (3)
N1—Ni1—N4—C5143.8 (2)N4—Ni1—O1—C2795.6 (3)
N8—Ni1—N4—C537.8 (2)C26—C21—C22—C232.0 (4)
O1—Ni1—N4—C548.9 (2)C27—C21—C22—C23178.1 (2)
O6—Ni1—N4—C5125.1 (2)C21—C22—C23—C240.6 (4)
C3—N4—C5—C6176.1 (2)C21—C22—C23—C28178.9 (2)
Ni1—N4—C5—C656.0 (3)C22—C23—C24—C251.0 (4)
N4—C5—C6—C772.3 (3)C28—C23—C24—C25177.3 (3)
C5—C6—C7—N872.0 (3)C23—C24—C25—O5177.2 (2)
C6—C7—N8—C9175.1 (2)C23—C24—C25—C261.2 (4)
C6—C7—N8—Ni155.9 (3)O5—C25—C26—C21178.6 (2)
N11—Ni1—N8—C7141.4 (2)C24—C25—C26—C210.2 (4)
O1—Ni1—N8—C750.8 (2)C22—C21—C26—C251.8 (4)
N4—Ni1—N8—C737.9 (2)C27—C21—C26—C25178.3 (2)
O6—Ni1—N8—C7128.7 (2)Ni1—O1—C27—O26.7 (4)
N11—Ni1—N8—C916.9 (2)Ni1—O1—C27—C21171.4 (2)
O1—Ni1—N8—C973.7 (2)C22—C21—C27—O2164.3 (3)
N4—Ni1—N8—C9162.5 (2)C26—C21—C27—O215.6 (4)
O6—Ni1—N8—C9106.8 (2)C22—C21—C27—O117.5 (4)
C7—N8—C9—C10169.3 (2)C26—C21—C27—O1162.7 (2)
Ni1—N8—C9—C1043.5 (2)C24—C23—C28—O431.6 (4)
N8—C9—C10—N1158.1 (3)C22—C23—C28—O4150.1 (3)
C9—C10—N11—C12169.3 (2)C24—C23—C28—O3148.3 (3)
C9—C10—N11—Ni139.5 (3)C22—C23—C28—O330.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.932.062.903 (3)150
N4—H4···O3i0.932.493.344 (3)153
N8—H8···O70.932.133.032 (3)164
N11—H11···O9ii0.932.203.018 (3)147
O5—H5···O3iii0.841.692.519 (3)169
O6—H6A···O70.90 (3)1.80 (3)2.670 (3)161 (4)
O6—H6B···O5iv0.90 (3)2.00 (3)2.864 (3)160 (4)
O7—H7A···O80.86 (3)1.88 (3)2.719 (3)164 (4)
O7—H7B···O10iii0.89 (3)1.91 (3)2.793 (3)172 (4)
O8—H8A···O90.88 (3)1.84 (3)2.712 (3)169 (4)
O8—H8B···O5v0.87 (3)1.97 (3)2.824 (3)167 (5)
O9—H9A···O100.85 (3)1.97 (3)2.824 (3)176 (4)
O9—H9B···O4vi0.88 (3)1.93 (3)2.801 (3)174 (4)
O10—H10A···O2vii0.92 (3)1.83 (3)2.739 (3)169 (3)
O10—H10B···O4v0.87 (3)1.85 (3)2.718 (3)174 (8)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x1/2, y+1/2, z1/2; (iii) x, y+1, z1/2; (iv) x+1/2, y+1/2, z+1/2; (v) x+1/2, y1/2, z+1; (vi) x+1/2, y+3/2, z+1/2; (vii) x+1/2, y+1/2, z+1.
(VII) catena-poly[terephthalato-1,4,8,11- -tetraazacyclotetradecanenickel(II)] monohydrate top
Crystal data top
C18H28N4NiO4·H2OF(000) = 936
Mr = 441.17Dx = 1.441 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 16.2155 (4) ÅCell parameters from 2402 reflections
b = 16.0404 (6) Åθ = 2.6–27.5°
c = 8.8937 (3) ŵ = 0.99 mm1
β = 118.4900 (16)°T = 150 K
V = 2033.14 (11) Å3Block, purple
Z = 40.18 × 0.16 × 0.16 mm
Data collection top
Kappa-CCD
diffractometer
2333 independent reflections
Radiation source: fine-focus sealed X-ray tube1622 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.088
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 020
Tmin = 0.842, Tmax = 0.858k = 020
12978 measured reflectionsl = 1110
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.0754P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2333 reflectionsΔρmax = 0.83 e Å3
134 parametersΔρmin = 0.85 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0193 (17)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.25000.25000.00000.0247 (2)
N10.17290 (19)0.34829 (15)0.0202 (3)0.0269 (6)
C20.2208 (2)0.3725 (2)0.2020 (4)0.0333 (8)
C30.2515 (2)0.2942 (2)0.3125 (4)0.0326 (8)
N40.31102 (19)0.24304 (15)0.2643 (3)0.0267 (6)
C50.3266 (2)0.1572 (2)0.3344 (4)0.0334 (8)
C60.3900 (2)0.1077 (2)0.2841 (4)0.0350 (8)
C70.3461 (2)0.08048 (19)0.0968 (4)0.0333 (8)
O10.14783 (15)0.16226 (13)0.0325 (3)0.0301 (5)
O20.03070 (16)0.22725 (14)0.0099 (3)0.0338 (6)
C110.0346 (2)0.07824 (19)0.0107 (4)0.0270 (7)
C120.0720 (2)0.0063 (2)0.0410 (4)0.0304 (7)
C130.0374 (2)0.07130 (19)0.0316 (4)0.0288 (7)
C140.0733 (2)0.16271 (19)0.0194 (4)0.0268 (7)
O30.00000.3041 (3)0.25000.0708 (14)
H10.11490.32660.00260.032*
H2A0.17780.40560.22840.040*
H2B0.27630.40730.22660.040*
H3A0.28710.30980.43480.039*
H3B0.19570.26180.29530.039*
H40.36930.26890.30910.032*
H5A0.26550.12840.29100.040*
H5B0.35570.15980.46070.040*
H6A0.41170.05730.35680.042*
H6B0.44610.14190.31040.042*
H7A0.38910.04120.08300.040*
H7B0.28660.05070.06560.040*
H120.12180.01040.06840.037*
H130.06290.12010.05410.035*
H30.008 (6)0.266 (3)0.190 (8)0.11 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0270 (4)0.0229 (3)0.0269 (3)0.0040 (2)0.0151 (3)0.0000 (2)
N10.0280 (14)0.0243 (14)0.0320 (14)0.0029 (11)0.0172 (12)0.0008 (11)
C20.0375 (18)0.0323 (18)0.0349 (18)0.0015 (15)0.0211 (15)0.0062 (14)
C30.0362 (19)0.036 (2)0.0298 (17)0.0042 (15)0.0192 (15)0.0021 (14)
N40.0276 (14)0.0258 (14)0.0274 (13)0.0035 (11)0.0137 (11)0.0009 (11)
C50.0346 (18)0.0344 (19)0.0300 (17)0.0040 (15)0.0145 (15)0.0068 (14)
C60.0358 (19)0.0306 (18)0.0353 (18)0.0008 (15)0.0143 (15)0.0076 (14)
C70.0320 (17)0.0245 (16)0.0445 (19)0.0025 (14)0.0192 (16)0.0020 (14)
O10.0306 (12)0.0257 (12)0.0394 (12)0.0067 (10)0.0210 (10)0.0021 (10)
O20.0329 (13)0.0280 (12)0.0438 (14)0.0021 (10)0.0211 (11)0.0024 (10)
C110.0264 (16)0.0257 (16)0.0277 (16)0.0025 (13)0.0119 (13)0.0049 (13)
C120.0258 (16)0.0329 (19)0.0352 (18)0.0029 (13)0.0166 (14)0.0023 (14)
C130.0291 (17)0.0241 (16)0.0355 (17)0.0034 (13)0.0173 (14)0.0020 (13)
C140.0267 (17)0.0262 (17)0.0268 (16)0.0044 (13)0.0121 (13)0.0027 (13)
O30.101 (4)0.065 (3)0.053 (3)0.0000.042 (3)0.000
Geometric parameters (Å, º) top
Ni1—N1i2.072 (3)C5—H5A0.99
Ni1—N12.072 (3)C5—H5B0.99
Ni1—N42.073 (3)C6—C71.530 (4)
Ni1—N4i2.073 (3)C6—H6A0.99
Ni1—O12.086 (2)C6—H6B0.99
Ni1—O1i2.086 (2)C7—N1i1.476 (4)
N1—C21.473 (4)C7—H7A0.99
N1—C7i1.476 (4)C7—H7B0.99
N1—H10.93O1—C141.269 (3)
C2—C31.524 (4)O2—C141.269 (4)
C2—H2A0.99C11—C121.388 (4)
C2—H2B0.99C11—C131.392 (4)
C3—N41.477 (4)C11—C141.510 (4)
C3—H3A0.99C12—C13ii1.385 (4)
C3—H3B0.99C12—H120.95
N4—C51.482 (4)C13—C12ii1.385 (4)
N4—H40.93C13—H130.95
C5—C61.525 (5)O3—H30.86 (7)
N1i—Ni1—N1180C5—N4—Ni1114.9 (2)
N1i—Ni1—N494.4 (2)C3—N4—H4107.4
N1—Ni1—N485.7 (2)C5—N4—H4107.4
N1i—Ni1—N4i85.7 (2)Ni1—N4—H4107.4
N1—Ni1—N4i94.4 (2)N4—C5—C6111.4 (3)
N4—Ni1—N4i180N4—C5—H5A109.4
N1i—Ni1—O187.0 (2)C6—C5—H5A109.4
N1—Ni1—O193.1 (2)N4—C5—H5B109.4
N4—Ni1—O192.22 (9)C6—C5—H5B109.4
N4i—Ni1—O187.78 (9)H5A—C5—H5B108.0
N1i—Ni1—O1i93.1 (2)C5—C6—C7116.1 (3)
N1—Ni1—O1i87.0 (2)C5—C6—H6A108.3
N4—Ni1—O1i87.78 (9)C7—C6—H6A108.3
N4i—Ni1—O1i92.22 (9)C5—C6—H6B108.3
O1—Ni1—O1i180C7—C6—H6B108.3
C2—N1—C7i113.2 (2)H6A—C6—H6B107.4
C2—N1—Ni1105.7 (2)N1i—C7—C6112.3 (3)
C7i—N1—Ni1117.4 (2)N1i—C7—H7A109.2
C2—N1—H1106.6C6—C7—H7A109.2
C7i—N1—H1106.6N1i—C7—H7B109.2
Ni1—N1—H1106.6C6—C7—H7B109.2
N1—C2—C3109.3 (3)H7A—C7—H7B107.9
N1—C2—H2A109.8C14—O1—Ni1135.4 (2)
C3—C2—H2A109.8C12—C11—C13119.1 (3)
N1—C2—H2B109.8C12—C11—C14120.4 (3)
C3—C2—H2B109.8C13—C11—C14120.5 (3)
H2A—C2—H2B108.3C13ii—C12—C11120.5 (3)
N4—C3—C2109.1 (2)C13ii—C12—H12119.7
N4—C3—H3A109.9C11—C12—H12119.7
C2—C3—H3A109.9C12ii—C13—C11120.3 (3)
N4—C3—H3B109.9C12ii—C13—H13119.8
C2—C3—H3B109.9C11—C13—H13119.8
H3A—C3—H3B108.3O1—C14—O2125.7 (3)
C3—N4—C5113.4 (2)O1—C14—C11115.9 (3)
C3—N4—Ni1105.9 (2)O2—C14—C11118.4 (3)
N4—Ni1—N1—C215.2 (2)O1i—Ni1—N4—C5133.1 (2)
N4i—Ni1—N1—C2164.8 (2)C3—N4—C5—C6178.8 (2)
O1—Ni1—N1—C2107.2 (2)Ni1—N4—C5—C659.1 (3)
O1i—Ni1—N1—C272.8 (2)N4—C5—C6—C772.6 (4)
N4—Ni1—N1—C7i142.5 (2)C5—C6—C7—N1i68.4 (4)
N4i—Ni1—N1—C7i37.5 (2)N1i—Ni1—O1—C14170.1 (3)
O1—Ni1—N1—C7i125.5 (2)N1—Ni1—O1—C149.9 (3)
O1i—Ni1—N1—C7i54.5 (2)N4—Ni1—O1—C1475.9 (3)
C7i—N1—C2—C3170.9 (3)N4i—Ni1—O1—C14104.1 (3)
Ni1—N1—C2—C341.1 (3)C13—C11—C12—C13ii0.9 (5)
N1—C2—C3—N456.1 (3)C14—C11—C12—C13ii179.4 (3)
C2—C3—N4—C5166.7 (3)C12—C11—C13—C12ii0.9 (5)
C2—C3—N4—Ni139.8 (3)C14—C11—C13—C12ii179.4 (3)
N1i—Ni1—N4—C3166.2 (2)Ni1—O1—C14—O214.0 (5)
N1—Ni1—N4—C313.8 (2)Ni1—O1—C14—C11164.5 (2)
O1—Ni1—N4—C379.1 (2)C12—C11—C14—O19.0 (4)
O1i—Ni1—N4—C3100.9 (2)C13—C11—C14—O1169.5 (3)
N1i—Ni1—N4—C540.2 (2)C12—C11—C14—O2172.3 (3)
N1—Ni1—N4—C5139.8 (2)C13—C11—C14—O29.2 (4)
O1—Ni1—N4—C546.9 (2)
Symmetry codes: (i) x+1/2, y+1/2, z; (ii) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.932.082.927 (4)151
N4—H4···O2iii0.932.333.182 (3)152
O3—H3···O20.86 (7)2.09 (4)2.865 (3)152 (5)
Symmetry code: (iii) x+1/2, y+1/2, z+1/2.
(VIII) top
Crystal data top
2(C15H25N4NiO4)·C10H28N4NiO2·2(ClO4)·0.86(H2O)F(000) = 1345
Mr = 1277.62Dx = 1.550 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.8295 (3) ÅCell parameters from 6029 reflections
b = 16.9416 (5) Åθ = 2.6–27.5°
c = 14.9596 (5) ŵ = 1.20 mm1
β = 93.6260 (13)°T = 150 K
V = 2739.13 (14) Å3Plate, purple
Z = 20.40 × 0.36 × 0.12 mm
Data collection top
Kappa-CCD
diffractometer
6277 independent reflections
Radiation source: fine-focus sealed X-ray tube5362 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
φ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
h = 014
Tmin = 0.646, Tmax = 0.869k = 021
20675 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0347P)2 + 1.8839P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.002
6277 reflectionsΔρmax = 0.45 e Å3
377 parametersΔρmin = 0.62 e Å3
12 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0031 (6)
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ni10.50000.50000.50000.02030 (10)
O10.38485 (14)0.60422 (9)0.51792 (10)0.0259 (3)
N10.39309 (15)0.43568 (10)0.58281 (11)0.0236 (3)
N40.37720 (15)0.46280 (10)0.39646 (11)0.0237 (3)
C20.27679 (19)0.41805 (12)0.52933 (14)0.0272 (4)
C30.30689 (19)0.39725 (12)0.43400 (14)0.0274 (4)
C50.4313 (2)0.44231 (13)0.31113 (14)0.0302 (5)
C60.5073 (2)0.50998 (14)0.27584 (14)0.0330 (5)
C70.6280 (2)0.52759 (14)0.32990 (14)0.0302 (5)
Ni20.05830 (2)0.726187 (13)0.219586 (15)0.01786 (9)
N210.24350 (16)0.74376 (10)0.25471 (11)0.0243 (3)
N240.11892 (16)0.65442 (9)0.11953 (10)0.0229 (3)
N280.12864 (16)0.70977 (10)0.18166 (11)0.0232 (3)
N2110.00371 (16)0.79631 (9)0.32214 (10)0.0229 (3)
C220.3101 (2)0.71693 (13)0.17691 (15)0.0309 (5)
C230.2520 (2)0.64054 (13)0.14163 (14)0.0293 (4)
C250.0468 (2)0.58163 (12)0.10260 (14)0.0290 (4)
C260.0892 (2)0.59926 (13)0.07795 (14)0.0312 (5)
C270.1634 (2)0.62875 (13)0.15456 (14)0.0286 (4)
C290.1968 (2)0.73968 (14)0.25759 (14)0.0302 (4)
C2100.1339 (2)0.81369 (12)0.29573 (14)0.0286 (4)
C2120.0701 (2)0.86785 (12)0.34468 (13)0.0295 (5)
C2130.2064 (2)0.84962 (13)0.36452 (14)0.0332 (5)
C2140.2767 (2)0.82481 (13)0.28417 (14)0.0307 (5)
O310.22188 (12)0.61039 (8)0.37722 (9)0.0241 (3)
O320.03561 (12)0.63084 (8)0.30767 (8)0.0203 (3)
O330.05499 (14)0.67231 (8)0.64061 (8)0.0238 (3)
O340.06560 (15)0.71343 (8)0.49881 (9)0.0294 (3)
C310.04684 (16)0.55333 (10)0.43868 (11)0.0159 (3)
C320.03135 (16)0.57742 (10)0.52690 (11)0.0163 (3)
C330.01418 (16)0.47667 (10)0.41329 (11)0.0170 (3)
C370.10573 (17)0.60403 (10)0.37045 (11)0.0175 (3)
C380.05380 (17)0.66177 (10)0.55700 (11)0.0180 (4)
O20.6171 (6)1.0018 (3)0.5361 (5)0.080 (3)0.430 (9)
Cl10.56740 (10)0.78843 (7)0.45060 (7)0.0347 (2)0.914 (4)
O30.4901 (2)0.76585 (13)0.52103 (15)0.0531 (7)0.914 (4)
O40.5410 (2)0.73697 (12)0.37519 (14)0.0498 (6)0.914 (4)
O50.5434 (3)0.86856 (12)0.42446 (17)0.0570 (7)0.914 (4)
O60.6948 (3)0.7793 (2)0.4816 (3)0.0500 (7)0.914 (4)
Cl210.5838 (12)0.8020 (8)0.4670 (9)0.0347 (2)0.086 (4)
O230.540 (2)0.8302 (13)0.5482 (13)0.052 (5)*0.086 (4)
O240.502 (2)0.7348 (12)0.4352 (15)0.052 (5)*0.086 (4)
O250.569 (3)0.8595 (15)0.3952 (15)0.052 (5)*0.086 (4)
O260.708 (3)0.773 (2)0.477 (3)0.052 (5)*0.086 (4)
H1A0.415 (3)0.6503 (16)0.5209 (19)0.050 (6)*
H1B0.328 (3)0.6076 (18)0.4750 (18)0.050 (6)*
H110.43330.38790.59440.028*
H40.32170.50390.38440.028*
H2A0.22140.46460.52860.033*
H2B0.23380.37330.55640.033*
H3A0.35650.34820.43420.033*
H3B0.22940.38830.39670.033*
H5A0.36400.42870.26590.036*
H5B0.48490.39530.32040.036*
H6A0.52650.49760.21360.040*
H6B0.45580.55830.27390.040*
H7A0.67480.47780.34010.036*
H7B0.67890.56350.29510.036*
H210.26510.71000.30210.029*
H240.11270.68370.06680.027*
H280.14790.74250.13290.028*
H2110.00260.76520.37340.027*
H22A0.39850.70820.19510.037*
H22B0.30460.75770.12940.037*
H23A0.29260.62320.08750.035*
H23B0.26290.59860.18750.035*
H25A0.05340.54800.15690.035*
H25B0.08190.55190.05320.035*
H26A0.09400.63940.02980.037*
H26B0.12890.55060.05330.037*
H27A0.25270.62730.13570.034*
H27B0.14940.59300.20660.034*
H29A0.19830.69870.30470.036*
H29B0.28330.75190.23680.036*
H10A0.13860.85610.25020.034*
H10B0.17660.83210.34840.034*
H12A0.03720.89360.39760.035*
H12B0.06110.90540.29400.035*
H13A0.21360.80690.40970.040*
H13B0.24690.89700.39160.040*
H14A0.25780.86200.23410.037*
H14B0.36680.82740.30020.037*
H330.02330.46070.35320.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.01959 (18)0.02151 (18)0.01963 (17)0.00139 (13)0.00010 (13)0.00117 (13)
O10.0260 (7)0.0237 (7)0.0277 (7)0.0037 (6)0.0020 (6)0.0016 (6)
N10.0234 (8)0.0237 (8)0.0237 (8)0.0016 (6)0.0010 (6)0.0001 (7)
N40.0235 (8)0.0243 (8)0.0231 (8)0.0019 (6)0.0010 (6)0.0020 (7)
C20.0241 (10)0.0266 (10)0.0309 (10)0.0013 (8)0.0018 (8)0.0004 (8)
C30.0243 (10)0.0262 (10)0.0312 (10)0.0007 (8)0.0016 (8)0.0017 (8)
C50.0333 (11)0.0340 (12)0.0229 (10)0.0001 (9)0.0006 (8)0.0060 (9)
C60.0377 (12)0.0393 (12)0.0221 (10)0.0013 (10)0.0023 (9)0.0010 (9)
C70.0324 (11)0.0345 (11)0.0245 (10)0.0008 (9)0.0080 (8)0.0001 (9)
Ni20.02472 (15)0.01504 (13)0.01393 (13)0.00146 (9)0.00205 (9)0.00220 (8)
N210.0288 (9)0.0223 (8)0.0221 (8)0.0018 (7)0.0029 (7)0.0061 (7)
N240.0338 (9)0.0179 (8)0.0173 (7)0.0045 (7)0.0046 (6)0.0026 (6)
N280.0281 (9)0.0235 (8)0.0179 (7)0.0023 (7)0.0001 (6)0.0021 (6)
N2110.0338 (9)0.0192 (8)0.0158 (7)0.0022 (7)0.0032 (6)0.0015 (6)
C220.0294 (11)0.0345 (12)0.0296 (11)0.0022 (9)0.0084 (9)0.0079 (9)
C230.0334 (11)0.0285 (11)0.0269 (10)0.0093 (9)0.0085 (8)0.0044 (8)
C250.0469 (13)0.0177 (9)0.0226 (9)0.0012 (9)0.0028 (9)0.0016 (8)
C260.0438 (13)0.0265 (10)0.0224 (10)0.0043 (9)0.0041 (9)0.0048 (8)
C270.0312 (11)0.0296 (11)0.0245 (10)0.0061 (8)0.0027 (8)0.0009 (8)
C290.0277 (11)0.0365 (12)0.0270 (10)0.0052 (9)0.0060 (8)0.0011 (9)
C2100.0357 (11)0.0276 (10)0.0231 (9)0.0098 (9)0.0060 (8)0.0007 (8)
C2120.0494 (13)0.0185 (9)0.0207 (9)0.0004 (9)0.0026 (9)0.0016 (8)
C2130.0465 (13)0.0269 (11)0.0253 (10)0.0099 (9)0.0052 (9)0.0005 (9)
C2140.0346 (11)0.0262 (10)0.0307 (11)0.0091 (9)0.0022 (9)0.0050 (9)
O310.0213 (7)0.0254 (7)0.0255 (7)0.0008 (5)0.0009 (5)0.0090 (6)
O320.0264 (7)0.0186 (6)0.0156 (6)0.0007 (5)0.0010 (5)0.0054 (5)
O330.0409 (8)0.0170 (6)0.0138 (6)0.0047 (6)0.0035 (5)0.0035 (5)
O340.0554 (10)0.0157 (6)0.0169 (6)0.0056 (6)0.0015 (6)0.0006 (5)
C310.0187 (8)0.0137 (8)0.0152 (8)0.0009 (6)0.0005 (6)0.0010 (6)
C320.0189 (8)0.0151 (8)0.0148 (8)0.0003 (6)0.0003 (6)0.0003 (6)
C330.0226 (9)0.0157 (8)0.0128 (7)0.0003 (7)0.0005 (6)0.0002 (6)
C370.0259 (9)0.0129 (8)0.0138 (8)0.0003 (7)0.0014 (7)0.0012 (6)
C380.0225 (9)0.0163 (8)0.0151 (8)0.0008 (7)0.0006 (7)0.0006 (7)
O20.081 (4)0.051 (3)0.104 (5)0.005 (3)0.023 (3)0.027 (3)
Cl10.0388 (4)0.0278 (5)0.0379 (5)0.0003 (3)0.0054 (3)0.0003 (3)
O30.0557 (14)0.0475 (13)0.0596 (14)0.0008 (10)0.0309 (11)0.0035 (10)
O40.0691 (15)0.0357 (11)0.0438 (12)0.0074 (10)0.0038 (10)0.0073 (9)
O50.086 (2)0.0241 (10)0.0598 (16)0.0048 (10)0.0016 (13)0.0006 (10)
O60.0388 (13)0.0518 (15)0.0589 (15)0.0083 (10)0.0002 (11)0.0090 (11)
Cl210.0388 (4)0.0278 (5)0.0379 (5)0.0003 (3)0.0054 (3)0.0003 (3)
Geometric parameters (Å, º) top
Ni1—N1i2.060 (2)C22—C231.519 (3)
Ni1—N12.060 (2)C22—H22A0.99
Ni1—N42.075 (2)C22—H22B0.99
Ni1—N4i2.075 (2)C23—H23A0.99
Ni1—O1i2.188 (2)C23—H23B0.99
Ni1—O12.188 (2)C25—C261.525 (3)
O1—H1A0.85 (3)C25—H25A0.99
O1—H1B0.86 (3)C25—H25B0.99
N1—C7i1.477 (3)C26—C271.525 (3)
N1—C21.479 (3)C26—H26A0.99
N1—H110.93C26—H26B0.99
N4—C31.477 (3)C27—H27A0.99
N4—C51.479 (3)C27—H27B0.99
N4—H40.93C29—C2101.521 (3)
C2—C31.524 (3)C29—H29A0.99
C2—H2A0.99C29—H29B0.99
C2—H2B0.99C210—H10A0.99
C3—H3A0.99C210—H10B0.99
C3—H3B0.99C212—C2131.519 (3)
C5—C61.525 (3)C212—H12A0.99
C5—H5A0.99C212—H12B0.99
C5—H5B0.99C213—C2141.523 (3)
C6—C71.523 (3)C213—H13A0.99
C6—H6A0.99C213—H13B0.99
C6—H6B0.99C214—H14A0.99
C7—N1i1.477 (3)C214—H14B0.99
C7—H7A0.99O31—C371.260 (2)
C7—H7B0.99O32—C371.255 (2)
Ni2—N212.063 (2)O33—C381.263 (2)
Ni2—N242.067 (2)O33—Ni2iii2.086 (2)
Ni2—N2112.085 (2)O34—C381.247 (2)
Ni2—O33ii2.085 (2)C31—C331.393 (2)
Ni2—N282.086 (2)C31—C321.401 (2)
Ni2—O322.109 (2)C31—C371.506 (2)
N21—C221.479 (3)C32—C33iv1.393 (2)
N21—C2141.480 (3)C32—C381.513 (2)
N21—H210.93C33—C32iv1.393 (2)
N24—C251.473 (3)C33—H330.95
N24—C231.477 (3)Cl1—O51.432 (2)
N24—H240.93Cl1—O61.436 (3)
N28—C271.474 (3)Cl1—O31.438 (2)
N28—C291.482 (3)Cl1—O41.440 (2)
N28—H280.93Cl21—O231.42 (2)
N211—C2101.469 (3)Cl21—O261.43 (2)
N211—C2121.479 (3)Cl21—O251.45 (2)
N211—H2110.93Cl21—O241.50 (2)
N1i—Ni1—N1180C210—N211—Ni2105.3 (2)
N1i—Ni1—N494.00 (6)C212—N211—Ni2116.1 (2)
N1—Ni1—N486.00 (6)C210—N211—H211107.3
N1i—Ni1—N4i85.99 (6)C212—N211—H211107.3
N1—Ni1—N4i94.01 (6)Ni2—N211—H211107.3
N4—Ni1—N4i180N21—C22—C23108.9 (2)
N1i—Ni1—O1i90.39 (6)N21—C22—H22A109.9
N1—Ni1—O1i89.60 (6)C23—C22—H22A109.9
N4—Ni1—O1i90.39 (6)N21—C22—H22B109.9
N4i—Ni1—O1i89.61 (6)C23—C22—H22B109.9
N1i—Ni1—O189.61 (6)H22A—C22—H22B108.3
N1—Ni1—O190.40 (6)N24—C23—C22108.6 (2)
N4—Ni1—O189.61 (6)N24—C23—H23A110.0
N4i—Ni1—O190.39 (6)C22—C23—H23A110.0
O1i—Ni1—O1180N24—C23—H23B110.0
Ni1—O1—H1A122 (2)C22—C23—H23B110.0
Ni1—O1—H1B110 (2)H23A—C23—H23B108.4
H1A—O1—H1B103 (3)N24—C25—C26111.8 (2)
C7i—N1—C2112.9 (2)N24—C25—H25A109.3
C7i—N1—Ni1115.7 (2)C26—C25—H25A109.3
C2—N1—Ni1105.9 (2)N24—C25—H25B109.3
C7i—N1—H11107.3C26—C25—H25B109.3
C2—N1—H11107.3H25A—C25—H25B107.9
Ni1—N1—H11107.3C27—C26—C25115.4 (2)
C3—N4—C5113.2 (2)C27—C26—H26A108.4
C3—N4—Ni1105.4 (2)C25—C26—H26A108.4
C5—N4—Ni1116.4 (2)C27—C26—H26B108.4
C3—N4—H4107.1C25—C26—H26B108.4
C5—N4—H4107.1H26A—C26—H26B107.5
Ni1—N4—H4107.1N28—C27—C26112.0 (2)
N1—C2—C3109.12 (16)N28—C27—H27A109.2
N1—C2—H2A109.9C26—C27—H27A109.2
C3—C2—H2A109.9N28—C27—H27B109.2
N1—C2—H2B109.9C26—C27—H27B109.2
C3—C2—H2B109.9H27A—C27—H27B107.9
H2A—C2—H2B108.3N28—C29—C210109.7 (2)
N4—C3—C2109.1 (2)N28—C29—H29A109.7
N4—C3—H3A109.9C210—C29—H29A109.7
C2—C3—H3A109.9N28—C29—H29B109.7
N4—C3—H3B109.9C210—C29—H29B109.7
C2—C3—H3B109.9H29A—C29—H29B108.2
H3A—C3—H3B108.3N211—C210—C29109.6 (2)
N4—C5—C6112.0 (2)N211—C210—H10A109.8
N4—C5—H5A109.2C29—C210—H10A109.8
C6—C5—H5A109.2N211—C210—H10B109.8
N4—C5—H5B109.2C29—C210—H10B109.8
C6—C5—H5B109.2H10A—C210—H10B108.2
H5A—C5—H5B107.9N211—C212—C213112.5 (2)
C7—C6—C5115.3 (2)N211—C212—H12A109.1
C7—C6—H6A108.4C213—C212—H12A109.1
C5—C6—H6A108.4N211—C212—H12B109.1
C7—C6—H6B108.4C213—C212—H12B109.1
C5—C6—H6B108.4H12A—C212—H12B107.8
H6A—C6—H6B107.5C212—C213—C214115.5 (2)
N1i—C7—C6112.1 (2)C212—C213—H13A108.4
N1i—C7—H7A109.2C214—C213—H13A108.4
C6—C7—H7A109.2C212—C213—H13B108.4
N1i—C7—H7B109.2C214—C213—H13B108.4
C6—C7—H7B109.2H13A—C213—H13B107.5
H7A—C7—H7B107.9N21—C214—C213111.5 (2)
N21—Ni2—N2485.48 (7)N21—C214—H14A109.3
N21—Ni2—N21194.80 (7)C213—C214—H14A109.3
N24—Ni2—N211178.71 (6)N21—C214—H14B109.3
N21—Ni2—O33ii90.39 (6)C213—C214—H14B109.3
N24—Ni2—O33ii93.99 (6)H14A—C214—H14B108.0
N211—Ni2—O33ii87.26 (6)C37—O32—Ni2131.0 (2)
N21—Ni2—N28178.82 (6)C38—O33—Ni2iii132.6 (2)
N24—Ni2—N2894.12 (7)C33—C31—C32119.0 (2)
N211—Ni2—N2885.63 (7)C33—C31—C37117.3 (2)
O33ii—Ni2—N2888.53 (6)C32—C31—C37123.6 (2)
N21—Ni2—O3295.81 (6)C33iv—C32—C31118.8 (2)
N24—Ni2—O3293.26 (6)C33iv—C32—C38119.1 (2)
N211—Ni2—O3285.47 (6)C31—C32—C38121.9 (2)
O33ii—Ni2—O32170.81 (5)C31—C33—C32iv122.2 (2)
N28—Ni2—O3285.32 (6)C31—C33—H33118.9
C22—N21—C214113.5 (2)C32iv—C33—H33118.9
C22—N21—Ni2105.7 (2)O32—C37—O31125.7 (2)
C214—N21—Ni2115.1 (2)O32—C37—C31116.8 (2)
C22—N21—H21107.4O31—C37—C31117.2 (2)
C214—N21—H21107.4O34—C38—O33126.7 (2)
Ni2—N21—H21107.4O34—C38—C32118.5 (2)
C25—N24—C23113.9 (2)O33—C38—C32114.8 (2)
C25—N24—Ni2115.3 (2)O5—Cl1—O6110.1 (2)
C23—N24—Ni2106.4 (2)O5—Cl1—O3110.4 (2)
C25—N24—H24106.9O6—Cl1—O3109.1 (2)
C23—N24—H24106.9O5—Cl1—O4109.7 (2)
Ni2—N24—H24106.9O6—Cl1—O4109.1 (2)
C27—N28—C29113.5 (2)O3—Cl1—O4108.5 (2)
C27—N28—Ni2115.2 (2)O23—Cl21—O26113 (2)
C29—N28—Ni2105.5 (2)O23—Cl21—O25113 (2)
C27—N28—H28107.4O26—Cl21—O25111 (2)
C29—N28—H28107.4O23—Cl21—O24108 (2)
Ni2—N28—H28107.4O26—Cl21—O24108 (2)
C210—N211—C212113.1 (2)O25—Cl21—O24104 (2)
N4—Ni1—N1—C7i140.2 (2)N28—Ni2—N211—C21016.1 (2)
N4i—Ni1—N1—C7i39.9 (2)O32—Ni2—N211—C210101.7 (2)
O1i—Ni1—N1—C7i129.4 (2)N21—Ni2—N211—C21236.9 (2)
O1—Ni1—N1—C7i50.6 (2)O33ii—Ni2—N211—C21253.3 (2)
N4—Ni1—N1—C214.3 (2)N28—Ni2—N211—C212142.0 (2)
N4i—Ni1—N1—C2165.7 (2)O32—Ni2—N211—C212132.3 (2)
O1i—Ni1—N1—C2104.8 (2)C214—N21—C22—C23169.4 (2)
O1—Ni1—N1—C275.2 (2)Ni2—N21—C22—C2342.4 (2)
N1i—Ni1—N4—C3165.4 (2)C25—N24—C23—C22167.9 (2)
N1—Ni1—N4—C314.6 (2)Ni2—N24—C23—C2239.8 (2)
O1i—Ni1—N4—C374.9 (2)N21—C22—C23—N2456.6 (2)
O1—Ni1—N4—C3105.1 (2)C23—N24—C25—C26178.6 (2)
N1i—Ni1—N4—C539.0 (2)Ni2—N24—C25—C2658.0 (2)
N1—Ni1—N4—C5141.0 (2)N24—C25—C26—C2771.7 (2)
O1i—Ni1—N4—C551.4 (2)C29—N28—C27—C26178.6 (2)
O1—Ni1—N4—C5128.6 (2)Ni2—N28—C27—C2656.8 (2)
C7i—N1—C2—C31678.0 (2)C25—C26—C27—N2871.1 (2)
Ni1—N1—C2—C340.5 (2)C27—N28—C29—C210166.0 (2)
C5—N4—C3—C2169.0 (2)Ni2—N28—C29—C21038.9 (2)
Ni1—N4—C3—C240.642)C212—N211—C210—C29169.7 (2)
N1—C2—C3—N456.3 (2)Ni2—N211—C210—C2941.8 (2)
C3—N4—C5—C6177.89 (2)N28—C29—C210—N21156.4 (2)
Ni1—N4—C5—C655.4 (2)C210—N211—C212—C213175.4 (2)
N4—C5—C6—C769.7 (2)Ni2—N211—C212—C21353.4 (2)
C5—C6—C7—N1i71.4 (2)N211—C212—C213—C21470.3 (2)
N24—Ni2—N21—C2216.1 (2)C22—N21—C214—C213179.8 (2)
N211—Ni2—N21—C22165.1 (2)Ni2—N21—C214—C21358.4 (2)
O33ii—Ni2—N21—C2277.9 (2)C212—C213—C214—N2173.2 (2)
O32—Ni2—N21—C22108.9 (2)N21—Ni2—O32—C3710.84 (16)
N24—Ni2—N21—C214142.1 (2)N24—Ni2—O32—C3796.62 (16)
N211—Ni2—N21—C21439.2 (2)N211—Ni2—O32—C3783.5 (2)
O33ii—Ni2—N21—C21448.1 (2)N28—Ni2—O32—C37169.5 (2)
O32—Ni2—N21—C214125.1 (2)C33—C31—C32—C33iv1.1 (3)
N21—Ni2—N24—C25140.5 (2)C37—C31—C32—C33iv174.3 (2)
O33ii—Ni2—N24—C25129.5 (2)C33—C31—C32—C38174.4 (2)
N28—Ni2—N24—C2540.7 (2)C37—C31—C32—C3810.2 (3)
O32—Ni2—N24—C2544.9 (2)C32—C31—C33—C32iv1.2 (3)
N21—Ni2—N24—C2313.2 (2)C37—C31—C33—C32iv174.6 (2)
O33ii—Ni2—N24—C23103.3 (2)Ni2—O32—C37—O3125.6 (3)
N28—Ni2—N24—C23167.9 (2)Ni2—O32—C37—C31160.6 (2)
O32—Ni2—N24—C2382.4 (2)C33—C31—C37—O3275.1 (2)
N24—Ni2—N28—C2740.1 (2)C32—C31—C37—O32109.4 (2)
N211—Ni2—N28—C27138.6 (2)C33—C31—C37—O3199.3 (2)
O33ii—Ni2—N28—C27134.0 (2)C32—C31—C37—O3176.3 (2)
O32—Ni2—N28—C2752.8 (2)Ni2iii—O33—C38—O347.0 (3)
N24—Ni2—N28—C29166.1 (2)Ni2iii—O33—C38—C32170.9 (2)
N211—Ni2—N28—C2912.7 (2)C33iv—C32—C38—O34163.1 (2)
O33ii—Ni2—N28—C29100.0 (2)C31—C32—C38—O3412.4 (3)
O32—Ni2—N28—C2973.2 (2)C33iv—C32—C38—O3315.0 (2)
N21—Ni2—N211—C210162.9 (2)C31—C32—C38—O33169.6 (2)
O33ii—Ni2—N211—C21072.7 (2)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2; (iii) x, y+3/2, z+1/2; (iv) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.85 (3)2.12 (3)2.965 (3)177 (3)
O1—H1A···O240.85 (3)2.17 (4)2.87 (2)139 (3)
O1—H1B···O310.86 (3)1.80 (3)2.662 (2)173 (3)
N1—H11···O4i0.932.183.066 (3)159
N1—H11···O24i0.932.253.12 (2)156
N4—H4···O310.932.103.017 (2)167
N21—H21···O310.932.102.928 (2)148
N24—H24···O34ii0.932.072.911 (2)150
N211—H211···O340.932.163.045 (2)159
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2.
 

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