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In the title complex, [Ni(C24H38N6)](BF4)2, the 14-membered hexaazacyclotetradecane macrocycle chelates to the Ni atom through its four secondary N atoms. The tetrafluoroborate ion interacts with the Ni atom at a distance of about 3 Å, and the coordination geometry of the Ni atom is regarded as tetragonally distorted octahedral. The Ni atom lies on an inversion center.
Supporting information
CCDC reference: 205544
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.037
- wR factor = 0.091
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C6
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... B1
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 38.00 Perc.
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 20.40 Deg.
F1A -B1 -F4 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.80 Deg.
F2 -B1 -F4A 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.20 Deg.
F1 -B1 -F2A 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
2 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), ORTEP-3 for Windows (Farugia, 1997) and
CAMERON (Watkin et al., 1996); software used to prepare material for publication: SHELXL97.
[1,8-Bis(2-phenylethyl)-1,3,6,8,10,13-hexaazacyclotetradecane]nickel(II)
ditetrafluoroborate
top
Crystal data top
[Ni(C24H38N6)](BF4)2 | F(000) = 668 |
Mr = 642.93 | Dx = 1.490 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 831 reflections |
a = 11.427 (2) Å | θ = 2.4–24.2° |
b = 8.329 (1) Å | µ = 0.76 mm−1 |
c = 15.622 (2) Å | T = 298 K |
β = 105.480 (3)° | Plate, yellow |
V = 1432.9 (4) Å3 | 0.39 × 0.16 × 0.04 mm |
Z = 2 | |
Data collection top
Bruker SMART 1K area-detector diffractometer | 3246 independent reflections |
Radiation source: normal-focus sealed tube | 2178 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 8.33 pixels mm-1 | θmax = 27.5°, θmin = 4.3° |
φ and ω scans | h = −9→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −10→10 |
Tmin = 0.757, Tmax = 0.970 | l = −20→10 |
8039 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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0447P)2] where P = (Fo2 + 2Fc2)/3 |
3246 reflections | (Δ/σ)max < 0.001 |
216 parameters | Δρmax = 0.29 e Å−3 |
45 restraints | Δρmin = −0.23 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 | Occ. (<1) |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.03493 (13) | |
B1 | 0.5678 (3) | 0.1617 (3) | 0.65217 (18) | 0.0508 (7) | |
F3 | 0.60713 (16) | 0.06447 (17) | 0.72421 (9) | 0.0771 (5) | |
F1 | 0.6015 (11) | 0.3145 (10) | 0.6727 (7) | 0.112 (4) | 0.55 |
F2 | 0.4470 (7) | 0.1504 (12) | 0.6248 (7) | 0.114 (4) | 0.55 |
F4 | 0.6137 (10) | 0.1063 (15) | 0.5858 (6) | 0.099 (3) | 0.55 |
F1A | 0.6429 (11) | 0.147 (2) | 0.5989 (9) | 0.128 (6) | 0.45 |
F2A | 0.5690 (13) | 0.3189 (11) | 0.6786 (7) | 0.097 (4) | 0.45 |
F4A | 0.4525 (9) | 0.1318 (11) | 0.6012 (8) | 0.079 (3) | 0.45 |
N1 | 0.42312 (15) | 0.59104 (19) | 0.58520 (11) | 0.0386 (4) | |
H1 | 0.4343 | 0.5199 | 0.6309 | 0.046* | |
N2 | 0.63625 (15) | 0.63609 (19) | 0.55158 (10) | 0.0397 (4) | |
H2 | 0.6328 | 0.7203 | 0.5139 | 0.048* | |
N3 | 0.78354 (16) | 0.5070 (2) | 0.48479 (12) | 0.0473 (4) | |
C1 | 0.29021 (19) | 0.6261 (3) | 0.55551 (15) | 0.0488 (6) | |
H1A | 0.2637 | 0.6615 | 0.6064 | 0.059* | |
H1B | 0.2770 | 0.7141 | 0.5133 | 0.059* | |
C2 | 0.4900 (2) | 0.7396 (2) | 0.62183 (14) | 0.0473 (5) | |
H2A | 0.4726 | 0.7693 | 0.6772 | 0.057* | |
H2B | 0.4664 | 0.8277 | 0.5801 | 0.057* | |
C3 | 0.6217 (2) | 0.7032 (3) | 0.63701 (13) | 0.0469 (5) | |
H3A | 0.6479 | 0.6256 | 0.6846 | 0.056* | |
H3B | 0.6697 | 0.8000 | 0.6529 | 0.056* | |
C4 | 0.7587 (2) | 0.5601 (3) | 0.56496 (15) | 0.0481 (5) | |
H4A | 0.8204 | 0.6370 | 0.5938 | 0.058* | |
H4B | 0.7645 | 0.4690 | 0.6046 | 0.058* | |
C5 | 0.8047 (2) | 0.6293 (3) | 0.42261 (14) | 0.0479 (5) | |
H5A | 0.7282 | 0.6807 | 0.3938 | 0.057* | |
H5B | 0.8344 | 0.5771 | 0.3770 | 0.057* | |
C6 | 0.8944 (2) | 0.7553 (3) | 0.46735 (16) | 0.0714 (8) | |
H6A | 0.9673 | 0.7026 | 0.5022 | 0.086* | |
H6B | 0.8601 | 0.8156 | 0.5080 | 0.086* | |
C7 | 0.9289 (2) | 0.8705 (3) | 0.40406 (15) | 0.0515 (6) | |
C8 | 1.0429 (2) | 0.8660 (3) | 0.39002 (18) | 0.0641 (7) | |
H8 | 1.0981 | 0.7890 | 0.4194 | 0.077* | |
C9 | 1.0769 (3) | 0.9717 (3) | 0.3340 (2) | 0.0703 (8) | |
H9 | 1.1540 | 0.9646 | 0.3251 | 0.084* | |
C10 | 0.9987 (3) | 1.0869 (3) | 0.29154 (17) | 0.0674 (7) | |
H10 | 1.0224 | 1.1602 | 0.2545 | 0.081* | |
C11 | 0.8850 (3) | 1.0942 (3) | 0.30366 (18) | 0.0673 (7) | |
H11 | 0.8308 | 1.1720 | 0.2741 | 0.081* | |
C12 | 0.8497 (2) | 0.9868 (3) | 0.35963 (17) | 0.0599 (6) | |
H12 | 0.7719 | 0.9931 | 0.3673 | 0.072* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0468 (2) | 0.02850 (19) | 0.02888 (19) | 0.00208 (17) | 0.00901 (15) | −0.00209 (16) |
B1 | 0.0602 (19) | 0.0468 (17) | 0.0439 (16) | 0.0056 (13) | 0.0110 (14) | 0.0103 (12) |
F3 | 0.1332 (13) | 0.0494 (8) | 0.0459 (8) | 0.0203 (9) | 0.0191 (8) | 0.0100 (7) |
F1 | 0.112 (4) | 0.055 (5) | 0.148 (7) | −0.041 (4) | −0.004 (4) | 0.020 (4) |
F2 | 0.046 (3) | 0.127 (5) | 0.167 (9) | 0.000 (3) | 0.024 (4) | 0.004 (4) |
F4 | 0.138 (8) | 0.119 (4) | 0.049 (3) | 0.003 (4) | 0.039 (4) | 0.006 (2) |
F1A | 0.072 (4) | 0.232 (16) | 0.096 (7) | 0.050 (7) | 0.048 (5) | 0.048 (8) |
F2A | 0.173 (10) | 0.040 (4) | 0.063 (4) | 0.021 (5) | 0.006 (5) | 0.008 (3) |
F4A | 0.091 (6) | 0.050 (3) | 0.081 (4) | −0.001 (3) | −0.006 (3) | 0.022 (3) |
N1 | 0.0508 (10) | 0.0308 (9) | 0.0346 (9) | 0.0037 (7) | 0.0118 (8) | 0.0002 (7) |
N2 | 0.0505 (10) | 0.0350 (9) | 0.0324 (9) | 0.0007 (8) | 0.0091 (8) | 0.0002 (7) |
N3 | 0.0468 (10) | 0.0490 (11) | 0.0461 (10) | 0.0023 (9) | 0.0125 (8) | 0.0005 (9) |
C1 | 0.0560 (14) | 0.0423 (13) | 0.0505 (14) | 0.0091 (11) | 0.0183 (11) | −0.0003 (10) |
C2 | 0.0688 (15) | 0.0341 (12) | 0.0428 (12) | −0.0039 (10) | 0.0215 (11) | −0.0084 (9) |
C3 | 0.0652 (15) | 0.0389 (12) | 0.0342 (12) | −0.0071 (10) | 0.0088 (11) | −0.0084 (9) |
C4 | 0.0478 (13) | 0.0539 (13) | 0.0396 (12) | 0.0011 (10) | 0.0065 (11) | 0.0026 (10) |
C5 | 0.0505 (13) | 0.0530 (14) | 0.0409 (12) | −0.0006 (11) | 0.0136 (10) | −0.0012 (10) |
C6 | 0.0846 (18) | 0.0723 (18) | 0.0509 (15) | −0.0236 (15) | 0.0068 (14) | 0.0021 (13) |
C7 | 0.0563 (15) | 0.0498 (14) | 0.0430 (13) | −0.0080 (11) | 0.0041 (11) | −0.0052 (11) |
C8 | 0.0563 (16) | 0.0535 (16) | 0.0734 (18) | 0.0010 (12) | 0.0016 (14) | −0.0027 (14) |
C9 | 0.0561 (16) | 0.072 (2) | 0.086 (2) | −0.0076 (14) | 0.0254 (15) | −0.0135 (16) |
C10 | 0.083 (2) | 0.0652 (18) | 0.0556 (16) | −0.0135 (15) | 0.0217 (15) | −0.0009 (14) |
C11 | 0.0751 (19) | 0.0611 (18) | 0.0585 (17) | 0.0098 (14) | 0.0053 (15) | 0.0062 (14) |
C12 | 0.0511 (14) | 0.0668 (17) | 0.0605 (16) | 0.0012 (13) | 0.0126 (12) | −0.0073 (14) |
Geometric parameters (Å, º) top
Ni1—N2 | 1.9205 (16) | C2—H2A | 0.9700 |
Ni1—N1 | 1.9346 (16) | C2—H2B | 0.9700 |
Ni1—F1 | 3.056 (11) | C3—H3A | 0.9700 |
Ni1—F2A | 3.084 (10) | C3—H3B | 0.9700 |
B1—F2 | 1.336 (8) | C4—H4A | 0.9700 |
B1—F1 | 1.343 (9) | C4—H4B | 0.9700 |
B1—F1A | 1.351 (11) | C5—C6 | 1.503 (3) |
B1—F4 | 1.362 (9) | C5—H5A | 0.9700 |
B1—F3 | 1.362 (3) | C5—H5B | 0.9700 |
B1—F4A | 1.368 (10) | C6—C7 | 1.504 (3) |
B1—F2A | 1.371 (10) | C6—H6A | 0.9700 |
N1—C2 | 1.486 (2) | C6—H6B | 0.9700 |
N1—C1 | 1.494 (3) | C7—C8 | 1.378 (3) |
N1—H1 | 0.9100 | C7—C12 | 1.379 (3) |
N2—C3 | 1.496 (2) | C8—C9 | 1.368 (4) |
N2—C4 | 1.499 (3) | C8—H8 | 0.9300 |
N2—H2 | 0.9100 | C9—C10 | 1.358 (4) |
N3—C4 | 1.427 (3) | C9—H9 | 0.9300 |
N3—C1i | 1.433 (3) | C10—C11 | 1.362 (4) |
N3—C5 | 1.471 (3) | C10—H10 | 0.9300 |
C1—N3i | 1.433 (3) | C11—C12 | 1.384 (4) |
C1—H1A | 0.9700 | C11—H11 | 0.9300 |
C1—H1B | 0.9700 | C12—H12 | 0.9300 |
C2—C3 | 1.492 (3) | | |
| | | |
N2i—Ni1—N1 | 93.09 (7) | N3i—C1—H1B | 108.6 |
N2—Ni1—N1 | 86.91 (7) | N1—C1—H1B | 108.6 |
N2i—Ni1—F1 | 98.41 (18) | H1A—C1—H1B | 107.6 |
N2—Ni1—F1 | 81.59 (17) | N1—C2—C3 | 106.58 (16) |
N1—Ni1—F1 | 74.1 (2) | N1—C2—H2A | 110.4 |
N1i—Ni1—F1 | 105.9 (2) | C3—C2—H2A | 110.4 |
N2i—Ni1—F2A | 94.2 (2) | N1—C2—H2B | 110.4 |
N2—Ni1—F2A | 85.8 (2) | C3—C2—H2B | 110.4 |
N1—Ni1—F2A | 67.8 (2) | H2A—C2—H2B | 108.6 |
N1i—Ni1—F2A | 112.2 (2) | C2—C3—N2 | 106.36 (17) |
F2—B1—F1 | 110.4 (7) | C2—C3—H3A | 110.5 |
F2—B1—F1A | 124.7 (8) | N2—C3—H3A | 110.5 |
F1—B1—F1A | 92.7 (9) | C2—C3—H3B | 110.5 |
F2—B1—F4 | 107.9 (7) | N2—C3—H3B | 110.5 |
F1—B1—F4 | 111.1 (7) | H3A—C3—H3B | 108.6 |
F1A—B1—F4 | 20.4 (10) | N3—C4—N2 | 113.93 (17) |
F2—B1—F3 | 107.9 (4) | N3—C4—H4A | 108.8 |
F1—B1—F3 | 110.9 (5) | N2—C4—H4A | 108.8 |
F1A—B1—F3 | 109.3 (7) | N3—C4—H4B | 108.8 |
F4—B1—F3 | 108.6 (6) | N2—C4—H4B | 108.8 |
F2—B1—F4A | 17.8 (10) | H4A—C4—H4B | 107.7 |
F1—B1—F4A | 118.8 (7) | N3—C5—C6 | 112.85 (18) |
F1A—B1—F4A | 107.2 (8) | N3—C5—H5A | 109.0 |
F4—B1—F4A | 90.1 (8) | C6—C5—H5A | 109.0 |
F3—B1—F4A | 115.2 (4) | N3—C5—H5B | 109.0 |
F2—B1—F2A | 95.1 (8) | C6—C5—H5B | 109.0 |
F1—B1—F2A | 17.2 (11) | H5A—C5—H5B | 107.8 |
F1A—B1—F2A | 108.5 (9) | C5—C6—C7 | 113.9 (2) |
F4—B1—F2A | 125.4 (8) | C5—C6—H6A | 108.8 |
F3—B1—F2A | 110.1 (5) | C7—C6—H6A | 108.8 |
F4A—B1—F2A | 106.3 (7) | C5—C6—H6B | 108.8 |
B1—F1—Ni1 | 104.5 (6) | C7—C6—H6B | 108.8 |
B1—F2A—Ni1 | 102.4 (5) | H6A—C6—H6B | 107.7 |
C2—N1—C1 | 109.41 (15) | C8—C7—C12 | 117.4 (2) |
C2—N1—Ni1 | 108.06 (12) | C8—C7—C6 | 120.8 (2) |
C1—N1—Ni1 | 118.28 (13) | C12—C7—C6 | 121.8 (2) |
C2—N1—H1 | 106.8 | C9—C8—C7 | 121.7 (2) |
C1—N1—H1 | 106.8 | C9—C8—H8 | 119.1 |
Ni1—N1—H1 | 106.8 | C7—C8—H8 | 119.1 |
C3—N2—C4 | 110.79 (16) | C10—C9—C8 | 120.3 (3) |
C3—N2—Ni1 | 108.91 (12) | C10—C9—H9 | 119.8 |
C4—N2—Ni1 | 115.56 (13) | C8—C9—H9 | 119.8 |
C3—N2—H2 | 107.1 | C9—C10—C11 | 119.4 (3) |
C4—N2—H2 | 107.1 | C9—C10—H10 | 120.3 |
Ni1—N2—H2 | 107.1 | C11—C10—H10 | 120.3 |
C4—N3—C1i | 113.22 (18) | C10—C11—C12 | 120.5 (3) |
C4—N3—C5 | 118.11 (18) | C10—C11—H11 | 119.7 |
C1i—N3—C5 | 115.26 (17) | C12—C11—H11 | 119.7 |
N3i—C1—N1 | 114.53 (16) | C7—C12—C11 | 120.6 (2) |
N3i—C1—H1A | 108.6 | C7—C12—H12 | 119.7 |
N1—C1—H1A | 108.6 | C11—C12—H12 | 119.7 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···F2A | 0.91 | 2.26 | 2.958 (11) | 133 |
N1—H1···F3ii | 0.91 | 2.46 | 3.096 (2) | 127 |
N1—H1···F1 | 0.91 | 2.52 | 3.137 (11) | 126 |
N2—H2···F4Ai | 0.91 | 2.18 | 3.029 (8) | 154 |
N2—H2···F2i | 0.91 | 2.37 | 3.203 (9) | 152 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+3/2. |
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