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In the title compound, [Ni(C15H30N6O3)](ClO4)2, the NiII atom is coordinated by three N and three O atoms from the 3,3′,3′′-(1,4,7-triaza­cyclo­nonane-1,4,7-tri­yl)tripropanamide (tcet) ligand in a pseudo-octa­hedral geometry. The [Ni(tcet)]2+ complex cations are linked by N—H...O hydrogen bonds to form zigzag chains, which are further connected into a three-dimensional network by N—H...O hydrogen bonds with ClO4 anions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013316/ob2011sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013316/ob2011Isup2.hkl
Contains datablock I

CCDC reference: 602837

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.055
  • wR factor = 0.134
  • Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

[3,3',3''-(1,4,7-Triazacyclononane-1,4,7-triyl)tripropanamide]nickel(II) bis(perchlorate) top
Crystal data top
[Ni(C15H30N6O3)](ClO4)2F(000) = 1248
Mr = 600.06Dx = 1.653 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1477 reflections
a = 18.544 (2) Åθ = 2.3–20.7°
b = 12.5781 (14) ŵ = 1.09 mm1
c = 10.7292 (12) ÅT = 298 K
β = 105.562 (2)°Block, purple
V = 2410.8 (5) Å30.34 × 0.33 × 0.31 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4726 independent reflections
Radiation source: fine-focus sealed tube3802 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
φ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 2222
Tmin = 0.70, Tmax = 0.72k = 1513
12942 measured reflectionsl = 1312
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.07P)2 + 1.9365P]
where P = (Fo2 + 2Fc2)/3
4726 reflections(Δ/σ)max < 0.001
316 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = 0.40 e Å3
Special details top

Experimental. tcet: ESMS (m/z): 343 (L+H+); IR (KBr, ν, cm-): 3406 (w), 1672 (s).

(I): IR (KBr, ν, cm-): 3442 (w), 1672 (s), 1595 (s), 1087 (m), 625 (m); UV–vis in an aqueous solution (nm) (ε; M-1 cm-1): 905 (43.4), 558 (10.8), 354 (10.3), 277?(2442).

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl21.05593 (5)0.88177 (8)0.25087 (9)0.0359 (2)
Ni10.74693 (3)0.91935 (4)0.21301 (5)0.03202 (15)
Cl10.58763 (5)0.37447 (7)0.18066 (9)0.0337 (2)
C10.8248 (3)1.0878 (4)0.3657 (5)0.0577 (13)
H1A0.84041.16150.37950.069*
H1B0.86751.04340.40560.069*
C20.7615 (3)1.0662 (4)0.4303 (5)0.0525 (12)
H2A0.78171.06560.52360.063*
H2B0.72451.12250.40810.063*
C30.6422 (2)0.9743 (4)0.3510 (5)0.0504 (11)
H3A0.62731.00960.42060.060*
H3B0.61910.90450.33900.060*
C40.6153 (3)1.0379 (4)0.2286 (5)0.0543 (12)
H4A0.56131.03080.19700.065*
H4B0.62661.11240.24770.065*
C50.6773 (3)1.0965 (3)0.0654 (5)0.0463 (10)
H5A0.63741.14850.04040.056*
H5B0.69031.07370.01220.056*
C60.7449 (3)1.1474 (3)0.1572 (5)0.0501 (11)
H6A0.76861.19520.10930.060*
H6B0.72881.18910.22100.060*
C70.8659 (3)1.0583 (4)0.1731 (5)0.0571 (13)
H7A0.89741.00050.21660.068*
H7B0.89451.12360.19340.068*
C80.8471 (3)1.0398 (4)0.0278 (5)0.0573 (12)
H8A0.81881.10070.01480.069*
H8B0.89371.03810.00300.069*
C90.8038 (3)0.9416 (4)0.0242 (4)0.0483 (11)
C100.7490 (3)0.8776 (4)0.4867 (4)0.0458 (10)
H10A0.72400.81190.45230.055*
H10B0.73210.89690.56180.055*
C110.8325 (3)0.8578 (4)0.5298 (4)0.0552 (12)
H11A0.85690.92280.56800.066*
H11B0.84230.80410.59720.066*
C120.8684 (2)0.8222 (4)0.4259 (5)0.0509 (11)
C130.6001 (3)0.9386 (3)0.0225 (5)0.0482 (11)
H13A0.62810.91450.03650.058*
H13B0.55970.98350.02610.058*
C140.5664 (2)0.8430 (4)0.0707 (5)0.0499 (11)
H14A0.53810.86790.12890.060*
H14B0.53110.81060.00290.060*
C150.6188 (2)0.7582 (3)0.1390 (4)0.0421 (9)
N10.80028 (19)1.0657 (3)0.2247 (3)0.0395 (8)
N20.7255 (2)0.9627 (3)0.3868 (3)0.0393 (8)
N30.65015 (18)1.0034 (3)0.1253 (3)0.0392 (8)
N40.8028 (3)0.9173 (4)0.1447 (4)0.0673 (13)
H4D0.79780.97650.19170.101*
H4E0.76410.87450.17720.101*
N50.9341 (2)0.7750 (3)0.4629 (4)0.0511 (10)
H5D0.95990.80320.53770.077*
H5E0.95880.78500.40340.077*
N60.5895 (2)0.6617 (3)0.1370 (5)0.0607 (11)
H6C0.62160.61440.12090.091*
H6D0.54690.65900.07450.091*
O10.77088 (17)0.8864 (3)0.0393 (3)0.0481 (7)
O20.83895 (16)0.8342 (2)0.3073 (3)0.0482 (7)
O30.68594 (16)0.7758 (2)0.1932 (3)0.0409 (6)
O110.57494 (16)0.3409 (2)0.0529 (3)0.0424 (7)
O120.59306 (17)0.2929 (3)0.2621 (3)0.0499 (8)
O130.53474 (17)0.4460 (3)0.1952 (3)0.0497 (7)
O140.65475 (17)0.4360 (2)0.2081 (3)0.0520 (8)
O211.13203 (16)0.8773 (2)0.2612 (3)0.0437 (7)
O221.02602 (16)0.9486 (2)0.1499 (3)0.0461 (7)
O231.04183 (16)0.9370 (2)0.3560 (3)0.0433 (7)
O241.01462 (16)0.7919 (2)0.2378 (3)0.0446 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.0350 (5)0.0387 (5)0.0343 (5)0.0139 (4)0.0098 (4)0.0038 (4)
Ni10.0341 (3)0.0301 (3)0.0297 (3)0.00180 (19)0.00483 (19)0.00107 (19)
Cl10.0367 (5)0.0332 (5)0.0352 (5)0.0014 (4)0.0166 (4)0.0119 (4)
C10.068 (3)0.048 (3)0.049 (3)0.028 (2)0.001 (2)0.008 (2)
C20.069 (3)0.050 (3)0.036 (2)0.013 (2)0.008 (2)0.009 (2)
C30.047 (2)0.051 (3)0.060 (3)0.000 (2)0.025 (2)0.014 (2)
C40.056 (3)0.041 (2)0.068 (3)0.003 (2)0.020 (2)0.010 (2)
C50.053 (3)0.033 (2)0.050 (3)0.0043 (18)0.009 (2)0.0104 (19)
C60.058 (3)0.037 (2)0.053 (3)0.0015 (19)0.010 (2)0.010 (2)
C70.052 (3)0.054 (3)0.069 (3)0.012 (2)0.023 (2)0.003 (2)
C80.066 (3)0.061 (3)0.054 (3)0.014 (2)0.031 (2)0.010 (2)
C90.049 (2)0.055 (3)0.042 (3)0.007 (2)0.016 (2)0.008 (2)
C100.066 (3)0.044 (2)0.027 (2)0.010 (2)0.0111 (19)0.0012 (18)
C110.059 (3)0.062 (3)0.032 (2)0.018 (2)0.008 (2)0.005 (2)
C120.035 (2)0.058 (3)0.052 (3)0.001 (2)0.0030 (19)0.019 (2)
C130.044 (2)0.042 (2)0.048 (3)0.0020 (18)0.0063 (19)0.004 (2)
C140.036 (2)0.051 (3)0.054 (3)0.0022 (19)0.0040 (19)0.001 (2)
C150.050 (2)0.037 (2)0.041 (2)0.0108 (18)0.0174 (19)0.0051 (18)
N10.0439 (19)0.0364 (18)0.0331 (18)0.0054 (14)0.0013 (14)0.0012 (14)
N20.052 (2)0.0349 (17)0.0319 (18)0.0054 (15)0.0135 (15)0.0047 (14)
N30.0389 (18)0.0396 (18)0.0352 (18)0.0045 (15)0.0035 (14)0.0042 (15)
N40.105 (4)0.067 (3)0.037 (2)0.001 (3)0.031 (2)0.005 (2)
N50.057 (2)0.0347 (19)0.054 (2)0.0200 (17)0.0008 (18)0.0027 (17)
N60.055 (2)0.043 (2)0.084 (3)0.0125 (18)0.019 (2)0.004 (2)
O10.0577 (19)0.0489 (17)0.0400 (17)0.0021 (15)0.0168 (14)0.0015 (14)
O20.0401 (16)0.0542 (18)0.0443 (18)0.0062 (13)0.0008 (13)0.0001 (15)
O30.0457 (16)0.0357 (14)0.0384 (16)0.0067 (12)0.0062 (13)0.0024 (12)
O110.0484 (16)0.0474 (16)0.0383 (16)0.0194 (13)0.0233 (13)0.0209 (13)
O120.0555 (19)0.0567 (19)0.0418 (17)0.0163 (15)0.0204 (14)0.0133 (14)
O130.0484 (17)0.0478 (17)0.0541 (19)0.0147 (14)0.0161 (15)0.0015 (15)
O140.0475 (18)0.0487 (18)0.0539 (19)0.0145 (14)0.0031 (14)0.0145 (15)
O210.0453 (16)0.0500 (17)0.0454 (17)0.0030 (13)0.0290 (13)0.0141 (14)
O220.0449 (16)0.0449 (16)0.0496 (18)0.0180 (13)0.0144 (13)0.0126 (14)
O230.0441 (16)0.0463 (16)0.0410 (16)0.0182 (13)0.0141 (13)0.0200 (13)
O240.0486 (17)0.0423 (16)0.0464 (17)0.0129 (13)0.0186 (13)0.0170 (13)
Geometric parameters (Å, º) top
Cl2—O241.351 (3)C6—H6B0.9700
Cl2—O221.366 (3)C7—N11.468 (6)
Cl2—O211.387 (3)C7—C81.522 (7)
Cl2—O231.408 (3)C7—H7A0.9700
Cl2—Ni15.6544 (12)C7—H7B0.9700
Ni1—O22.039 (3)C8—C91.496 (7)
Ni1—O12.071 (3)C8—H8A0.9700
Ni1—N12.077 (3)C8—H8B0.9700
Ni1—N32.078 (3)C9—O11.242 (5)
Ni1—N22.081 (3)C9—N41.324 (6)
Ni1—O32.111 (3)C10—N21.495 (5)
Cl1—O121.334 (3)C10—C111.514 (7)
Cl1—O131.370 (3)C10—H10A0.9700
Cl1—O111.393 (3)C10—H10B0.9700
Cl1—O141.428 (3)C11—C121.511 (7)
C1—N11.485 (6)C11—H11A0.9700
C1—C21.539 (7)C11—H11B0.9700
C1—H1A0.9700C12—O21.252 (6)
C1—H1B0.9700C12—N51.316 (6)
C2—N21.480 (5)C13—N31.482 (5)
C2—H2A0.9700C13—C141.508 (6)
C2—H2B0.9700C13—H13A0.9700
C3—N21.497 (6)C13—H13B0.9700
C3—C41.504 (7)C14—C151.495 (6)
C3—H3A0.9700C14—H14A0.9700
C3—H3B0.9700C14—H14B0.9700
C4—N31.489 (6)C15—O31.245 (5)
C4—H4A0.9700C15—N61.327 (6)
C4—H4B0.9700N4—H4D0.8900
C5—N31.486 (5)N4—H4E0.8900
C5—C61.514 (6)N5—H5D0.8900
C5—H5A0.9700N5—H5E0.8900
C5—H5B0.9700N6—H6C0.8900
C6—N11.496 (5)N6—H6D0.8900
C6—H6A0.9700
O24—Cl2—O22109.5 (2)N1—C7—H7A108.7
O24—Cl2—O21120.7 (2)C8—C7—H7A108.7
O22—Cl2—O21106.05 (18)N1—C7—H7B108.7
O24—Cl2—O23105.90 (17)C8—C7—H7B108.7
O22—Cl2—O23102.1 (2)H7A—C7—H7B107.6
O21—Cl2—O23111.08 (19)C9—C8—C7117.4 (4)
O24—Cl2—Ni161.78 (14)C9—C8—H8A107.9
O22—Cl2—Ni172.76 (13)C7—C8—H8A107.9
O21—Cl2—Ni1177.49 (14)C9—C8—H8B107.9
O23—Cl2—Ni167.29 (12)C7—C8—H8B107.9
O2—Ni1—O189.33 (13)H8A—C8—H8B107.2
O2—Ni1—N196.54 (13)O1—C9—N4121.7 (5)
O1—Ni1—N191.04 (13)O1—C9—C8123.4 (4)
O2—Ni1—N3176.62 (14)N4—C9—C8114.9 (4)
O1—Ni1—N393.56 (13)N2—C10—C11114.4 (4)
N1—Ni1—N385.17 (14)N2—C10—H10A108.6
O2—Ni1—N291.63 (14)C11—C10—H10A108.6
O1—Ni1—N2176.18 (13)N2—C10—H10B108.6
N1—Ni1—N285.18 (13)C11—C10—H10B108.6
N3—Ni1—N285.60 (14)H10A—C10—H10B107.6
O2—Ni1—O387.42 (12)C12—C11—C10116.1 (4)
O1—Ni1—O388.66 (12)C12—C11—H11A108.3
N1—Ni1—O3176.02 (12)C10—C11—H11A108.3
N3—Ni1—O390.89 (12)C12—C11—H11B108.3
N2—Ni1—O395.08 (12)C10—C11—H11B108.3
O2—Ni1—Cl239.04 (9)H11A—C11—H11B107.4
O1—Ni1—Cl265.79 (9)O2—C12—N5118.5 (5)
N1—Ni1—Cl267.22 (10)O2—C12—C11123.8 (4)
N3—Ni1—Cl2144.14 (10)N5—C12—C11117.7 (4)
N2—Ni1—Cl2113.00 (10)N3—C13—C14114.7 (4)
O3—Ni1—Cl2116.17 (8)N3—C13—H13A108.6
O12—Cl1—O13111.1 (2)C14—C13—H13A108.6
O12—Cl1—O11112.0 (2)N3—C13—H13B108.6
O13—Cl1—O11112.0 (2)C14—C13—H13B108.6
O12—Cl1—O14111.9 (2)H13A—C13—H13B107.6
O13—Cl1—O14103.4 (2)C15—C14—C13117.6 (4)
O11—Cl1—O14105.99 (18)C15—C14—H14A107.9
N1—C1—C2111.3 (4)C13—C14—H14A107.9
N1—C1—H1A109.4C15—C14—H14B107.9
C2—C1—H1A109.4C13—C14—H14B107.9
N1—C1—H1B109.4H14A—C14—H14B107.2
C2—C1—H1B109.4O3—C15—N6121.5 (4)
H1A—C1—H1B108.0O3—C15—C14122.6 (4)
N2—C2—C1110.3 (4)N6—C15—C14115.9 (4)
N2—C2—H2A109.6C7—N1—C1109.7 (4)
C1—C2—H2A109.6C7—N1—C6113.1 (4)
N2—C2—H2B109.6C1—N1—C6110.3 (4)
C1—C2—H2B109.6C7—N1—Ni1110.5 (3)
H2A—C2—H2B108.1C1—N1—Ni1103.8 (3)
N2—C3—C4110.7 (4)C6—N1—Ni1109.0 (3)
N2—C3—H3A109.5C2—N2—C10112.6 (3)
C4—C3—H3A109.5C2—N2—C3110.0 (4)
N2—C3—H3B109.5C10—N2—C3109.6 (3)
C4—C3—H3B109.5C2—N2—Ni1109.6 (3)
H3A—C3—H3B108.1C10—N2—Ni1111.5 (3)
N3—C4—C3112.8 (4)C3—N2—Ni1103.2 (3)
N3—C4—H4A109.0C13—N3—C5109.2 (3)
C3—C4—H4A109.0C13—N3—C4113.8 (4)
N3—C4—H4B109.0C5—N3—C4111.0 (3)
C3—C4—H4B109.0C13—N3—Ni1110.5 (3)
H4A—C4—H4B107.8C5—N3—Ni1104.2 (2)
N3—C5—C6111.6 (4)C4—N3—Ni1107.8 (3)
N3—C5—H5A109.3C9—N4—H4D109.3
C6—C5—H5A109.3C9—N4—H4E108.7
N3—C5—H5B109.3H4D—N4—H4E109.5
C6—C5—H5B109.3C12—N5—H5D108.9
H5A—C5—H5B108.0C12—N5—H5E109.5
N1—C6—C5111.4 (3)H5D—N5—H5E109.5
N1—C6—H6A109.3C15—N6—H6C108.9
C5—C6—H6A109.3C15—N6—H6D108.9
N1—C6—H6B109.3H6C—N6—H6D109.5
C5—C6—H6B109.3C9—O1—Ni1129.6 (3)
H6A—C6—H6B108.0C12—O2—Ni1130.3 (3)
N1—C7—C8114.3 (4)C15—O3—Ni1129.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4E···O3i0.892.553.405 (6)160
N4—H4D···O21ii0.892.483.242 (5)144
N5—H5D···O24iii0.892.433.046 (5)127
N5—H5E···O240.892.283.170 (5)173
N5—H5E···O230.892.593.270 (5)134
N6—H6C···O140.892.443.100 (5)131
N6—H6D···O11iv0.892.303.181 (5)168
Symmetry codes: (i) x, y+3/2, z1/2; (ii) x+2, y+2, z; (iii) x, y+3/2, z+1/2; (iv) x+1, y+1, z.
 

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