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In the title complex, [Ni(C8H4O4)(C12H30N6)]n, the 14-membered hexaazacyclotetradecane macrocycle ring chelates to the Ni atom through its four secondary N atoms; the Ni atom and the terephthalate anion lie on inversion centers. The terephthalate dianion links adjacent nickel–macrocycle cations through the carboxyl O atoms [Ni—O 2.144 (2) Å] into a linear chain.
Supporting information
CCDC reference: 236042
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.030
- wR factor = 0.081
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT761_ALERT_1_A CIF Contains no X-H Bonds ...................... ?
PLAT762_ALERT_1_A CIF Contains no X-Y-H or H-Y-H Angles .......... ?
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.82 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.11 Ratio
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ?
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
catena-Poly[[(3,10-diethyl-1,3,5,8,10,12-hexaazacyclotetradecane)nickel(II)]- µ-terephthalato]
top
Crystal data top
[Ni(C8H4O4)·(C12H30N6)] | Z = 1 |
Mr = 481.24 | F(000) = 256 |
Triclinic, P1 | Dx = 1.421 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5818 (5) Å | Cell parameters from 2995 reflections |
b = 8.3976 (5) Å | θ = 4.0–30.0° |
c = 9.7596 (6) Å | µ = 0.90 mm−1 |
α = 105.506 (1)° | T = 298 K |
β = 97.283 (1)° | Plate, yellow |
γ = 105.853 (1)° | 0.27 × 0.23 × 0.08 mm |
V = 562.45 (6) Å3 | |
Data collection top
Bruker SMART 1K area-detector diffractometer | 2500 independent reflections |
Radiation source: medium-focus sealed tube | 2397 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.010 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 4.3° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −7→10 |
Tmin = 0.792, Tmax = 0.931 | l = −12→12 |
3389 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0496P)2 + 0.1456P] where P = (Fo2 + 2Fc2)/3 |
2500 reflections | (Δ/σ)max = 0.001 |
143 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.02670 (10) | |
O1 | 0.70930 (17) | 0.50960 (15) | 0.67450 (13) | 0.0394 (3) | |
O2 | 0.7174 (3) | 0.23744 (19) | 0.63580 (16) | 0.0692 (5) | |
N1 | 0.7031 (2) | 0.53250 (19) | 0.37877 (16) | 0.0368 (3) | |
H1 | 0.8043 | 0.5137 | 0.4242 | 0.044* | |
N2 | 0.5859 (2) | 0.2276 (2) | 0.22423 (17) | 0.0437 (4) | |
N3 | 0.41514 (19) | 0.23181 (17) | 0.42201 (14) | 0.0322 (3) | |
H3 | 0.4980 | 0.1968 | 0.4730 | 0.039* | |
C1 | 0.6401 (3) | 0.4055 (3) | 0.2276 (2) | 0.0444 (4) | |
H1A | 0.5347 | 0.4261 | 0.1763 | 0.053* | |
H1B | 0.7414 | 0.4263 | 0.1764 | 0.053* | |
C2 | 0.4131 (3) | 0.1583 (2) | 0.26518 (18) | 0.0398 (4) | |
H2A | 0.3839 | 0.0328 | 0.2409 | 0.048* | |
H2B | 0.3134 | 0.1802 | 0.2080 | 0.048* | |
C3 | 0.2329 (3) | 0.1704 (2) | 0.4606 (2) | 0.0434 (4) | |
H3A | 0.2052 | 0.0491 | 0.4563 | 0.052* | |
H3B | 0.1342 | 0.1790 | 0.3920 | 0.052* | |
C4 | 0.7592 (3) | 0.7181 (3) | 0.3862 (2) | 0.0477 (4) | |
H4A | 0.6692 | 0.7356 | 0.3166 | 0.057* | |
H4B | 0.8814 | 0.7517 | 0.3622 | 0.057* | |
C5 | 0.7394 (3) | 0.1609 (3) | 0.2609 (2) | 0.0546 (5) | |
H5A | 0.7325 | 0.1348 | 0.3514 | 0.066* | |
H5B | 0.8584 | 0.2509 | 0.2760 | 0.066* | |
C6 | 0.7338 (5) | 0.0014 (4) | 0.1460 (3) | 0.0787 (8) | |
H6A | 0.6194 | −0.0903 | 0.1344 | 0.118* | |
H6B | 0.8392 | −0.0343 | 0.1738 | 0.118* | |
H6C | 0.7391 | 0.0259 | 0.0558 | 0.118* | |
C7 | 0.7602 (2) | 0.3927 (2) | 0.71099 (17) | 0.0337 (3) | |
C8 | 0.8831 (2) | 0.4493 (2) | 0.86186 (16) | 0.0278 (3) | |
C9 | 0.9303 (2) | 0.6184 (2) | 0.95599 (17) | 0.0321 (3) | |
H9 | 0.8833 | 0.6985 | 0.9272 | 0.038* | |
C10 | 0.9536 (2) | 0.3308 (2) | 0.90788 (17) | 0.0317 (3) | |
H10 | 0.9223 | 0.2168 | 0.8466 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.03022 (16) | 0.02514 (15) | 0.02236 (15) | 0.00937 (10) | −0.00228 (10) | 0.00683 (10) |
O1 | 0.0460 (7) | 0.0347 (6) | 0.0326 (6) | 0.0147 (5) | −0.0122 (5) | 0.0105 (5) |
O2 | 0.1018 (13) | 0.0464 (8) | 0.0435 (8) | 0.0420 (8) | −0.0340 (8) | −0.0070 (6) |
N1 | 0.0371 (7) | 0.0376 (7) | 0.0348 (7) | 0.0131 (6) | 0.0043 (6) | 0.0104 (6) |
N2 | 0.0488 (8) | 0.0448 (8) | 0.0353 (8) | 0.0237 (7) | 0.0035 (6) | 0.0027 (6) |
N3 | 0.0342 (7) | 0.0286 (6) | 0.0300 (7) | 0.0111 (5) | −0.0048 (5) | 0.0078 (5) |
C1 | 0.0509 (10) | 0.0505 (10) | 0.0320 (9) | 0.0186 (8) | 0.0106 (7) | 0.0101 (7) |
C2 | 0.0456 (9) | 0.0322 (8) | 0.0318 (8) | 0.0144 (7) | −0.0080 (7) | 0.0000 (6) |
C3 | 0.0396 (9) | 0.0313 (8) | 0.0522 (11) | 0.0053 (7) | 0.0023 (8) | 0.0114 (7) |
C4 | 0.0507 (10) | 0.0425 (10) | 0.0507 (11) | 0.0095 (8) | 0.0168 (9) | 0.0190 (8) |
C5 | 0.0567 (12) | 0.0688 (14) | 0.0412 (10) | 0.0368 (11) | 0.0046 (9) | 0.0078 (9) |
C6 | 0.100 (2) | 0.0658 (15) | 0.0746 (17) | 0.0551 (15) | 0.0066 (15) | 0.0064 (13) |
C7 | 0.0378 (8) | 0.0374 (8) | 0.0254 (7) | 0.0178 (7) | −0.0040 (6) | 0.0080 (6) |
C8 | 0.0277 (7) | 0.0326 (7) | 0.0233 (7) | 0.0119 (6) | −0.0012 (5) | 0.0100 (6) |
C9 | 0.0363 (8) | 0.0319 (7) | 0.0295 (7) | 0.0160 (6) | −0.0027 (6) | 0.0113 (6) |
C10 | 0.0371 (8) | 0.0282 (7) | 0.0271 (7) | 0.0131 (6) | −0.0036 (6) | 0.0063 (6) |
Geometric parameters (Å, º) top
Ni1—N3 | 2.0574 (13) | N2—C5 | 1.468 (2) |
Ni1—N1 | 2.0617 (14) | N3—C3 | 1.471 (2) |
Ni1—O1 | 2.1440 (11) | N3—C2 | 1.486 (2) |
O1—C7 | 1.2644 (19) | C3—C4i | 1.521 (3) |
O2—C7 | 1.241 (2) | C5—C6 | 1.485 (3) |
N1—C4 | 1.478 (2) | C7—C8 | 1.516 (2) |
N1—C1 | 1.498 (2) | C8—C9 | 1.389 (2) |
N2—C1 | 1.426 (3) | C8—C10 | 1.395 (2) |
N2—C2 | 1.434 (3) | C9—C10ii | 1.385 (2) |
| | | |
N3—Ni1—N1 | 94.25 (6) | C2—N3—Ni1 | 114.62 (10) |
N3i—Ni1—N1 | 85.75 (6) | N2—C1—N1 | 113.35 (15) |
N3—Ni1—O1 | 92.27 (5) | N2—C2—N3 | 114.44 (13) |
N3i—Ni1—O1 | 87.73 (5) | N3—C3—C4i | 109.04 (14) |
N1—Ni1—O1 | 88.64 (6) | N1—C4—C3i | 109.17 (15) |
N1i—Ni1—O1 | 91.36 (6) | N2—C5—C6 | 112.85 (18) |
C7—O1—Ni1 | 132.79 (11) | O2—C7—O1 | 126.14 (14) |
C4—N1—C1 | 114.75 (15) | O2—C7—C8 | 117.72 (14) |
C4—N1—Ni1 | 106.09 (11) | O1—C7—C8 | 116.14 (14) |
C1—N1—Ni1 | 112.67 (11) | C9—C8—C10 | 118.61 (13) |
C1—N2—C2 | 118.14 (14) | C9—C8—C7 | 121.55 (13) |
C1—N2—C5 | 116.07 (17) | C10—C8—C7 | 119.83 (14) |
C2—N2—C5 | 116.98 (17) | C10ii—C9—C8 | 120.82 (14) |
C3—N3—C2 | 113.98 (13) | C9ii—C10—C8 | 120.57 (14) |
C3—N3—Ni1 | 106.17 (10) | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.91 | 2.03 | 2.878 (2) | 154 |
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