In the title structure, [Ni(C
11H
15N
2O)(C
11H
16N
2O)]ClO
4, there are two independent ion pairs in the asymmetric unit. In each cation, the Ni
II atom is six-coordinated in a slightly distorted octahedral geometry by two phenolate O atoms, two imine N atoms and two amine N atoms from two Schiff base ligands, in one of which the phenolate O atom is protonated. In the crystal structure, anions and cations are linked through intermolecular O—H
O, N—H
O and weak C—H
O hydrogen bonds, forming one-dimensional chains containing hydrogen-bonded cation dimers.
Supporting information
CCDC reference: 613761
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- Disorder in solvent or counterion
- R factor = 0.057
- wR factor = 0.156
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C31
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl2
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.07
PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 23.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2 .. CL1 .. 2.92 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. CL2 .. 2.95 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported N2 .. CL1 .. 3.81 Ang.
PLAT481_ALERT_4_C Long D...A H-Bond Reported N8 .. CL2 .. 3.84 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
12 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
4 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
7 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998)'; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
Bis{2-[2-(ethylamino)ethyliminomethyl]phenolato}nickel(II) perchlorate
top
Crystal data top
[Ni(C11H15N2O)(C11H16N2O)]ClO4 | Z = 4 |
Mr = 541.67 | F(000) = 1136 |
Triclinic, P1 | Dx = 1.455 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.813 (2) Å | Cell parameters from 3297 reflections |
b = 13.850 (2) Å | θ = 2.4–24.3° |
c = 13.979 (2) Å | µ = 0.94 mm−1 |
α = 100.24 (2)° | T = 298 K |
β = 106.14 (2)° | Block, green |
γ = 98.45 (2)° | 0.25 × 0.10 × 0.10 mm |
V = 2472.9 (7) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 9586 independent reflections |
Radiation source: fine-focus sealed tube | 6741 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
ω scans | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→17 |
Tmin = 0.800, Tmax = 0.912 | k = −17→17 |
19417 measured reflections | l = −17→17 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.076P)2 + 0.0425P] where P = (Fo2 + 2Fc2)/3 |
9586 reflections | (Δ/σ)max < 0.001 |
663 parameters | Δρmax = 0.81 e Å−3 |
74 restraints | Δρmin = −0.62 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 | 0.60434 (4) | 0.19091 (4) | 0.31777 (4) | 0.03301 (15) | |
Ni2 | 0.90966 (4) | 0.29019 (4) | 0.18112 (4) | 0.03409 (15) | |
Cl1 | 0.27062 (14) | 0.11242 (13) | 0.39909 (15) | 0.0895 (5) | |
Cl2 | 0.79467 (10) | 0.63561 (10) | 0.95224 (11) | 0.0655 (4) | |
O1 | 0.71604 (19) | 0.3228 (2) | 0.3371 (2) | 0.0379 (6) | |
O2 | 0.67468 (19) | 0.12334 (18) | 0.21491 (19) | 0.0354 (6) | |
O3 | 0.7507 (2) | 0.22541 (19) | 0.1176 (2) | 0.0359 (6) | |
O4 | 0.88671 (19) | 0.30452 (19) | 0.32474 (19) | 0.0360 (6) | |
O5 | 0.3672 (3) | 0.0878 (3) | 0.4421 (4) | 0.1052 (15) | |
O6 | 0.1938 (4) | 0.0252 (4) | 0.3666 (4) | 0.1190 (17) | |
O7 | 0.2452 (4) | 0.1795 (4) | 0.4726 (5) | 0.148 (2) | |
O8 | 0.2785 (5) | 0.1588 (5) | 0.3220 (5) | 0.179 (3) | |
O9 | 0.7082 (8) | 0.5732 (8) | 0.8715 (9) | 0.140 (4) | 0.67 (2) |
O10 | 0.8731 (7) | 0.5826 (7) | 0.9650 (11) | 0.092 (3) | 0.67 (2) |
O12 | 0.7605 (16) | 0.6568 (6) | 1.0353 (11) | 0.138 (6) | 0.67 (2) |
O9' | 0.6926 (7) | 0.6006 (19) | 0.929 (2) | 0.135 (11) | 0.33 (2) |
O12' | 0.837 (2) | 0.6685 (12) | 1.0630 (7) | 0.102 (6) | 0.33 (2) |
O10' | 0.848 (2) | 0.5622 (14) | 0.926 (2) | 0.111 (9) | 0.33 (2) |
O11 | 0.8229 (3) | 0.7215 (3) | 0.9173 (4) | 0.1100 (16) | |
N1 | 0.5092 (2) | 0.2531 (3) | 0.2181 (2) | 0.0387 (8) | |
N2 | 0.4711 (3) | 0.0709 (3) | 0.2645 (3) | 0.0434 (8) | |
N3 | 0.6919 (2) | 0.1254 (2) | 0.4194 (2) | 0.0354 (7) | |
N4 | 0.5646 (3) | 0.2525 (3) | 0.4507 (3) | 0.0435 (8) | |
N5 | 0.8682 (3) | 0.4208 (2) | 0.1598 (3) | 0.0412 (8) | |
N6 | 1.0598 (3) | 0.3861 (3) | 0.2463 (3) | 0.0426 (8) | |
N7 | 0.9552 (2) | 0.1606 (2) | 0.2026 (3) | 0.0400 (8) | |
N8 | 0.9324 (3) | 0.2431 (3) | 0.0351 (3) | 0.0461 (9) | |
C1 | 0.6055 (3) | 0.4258 (3) | 0.2622 (3) | 0.0410 (10) | |
C2 | 0.7001 (3) | 0.4146 (3) | 0.3241 (3) | 0.0364 (9) | |
C3 | 0.7785 (3) | 0.4984 (3) | 0.3703 (3) | 0.0495 (11) | |
H3 | 0.8417 | 0.4909 | 0.4106 | 0.059* | |
C4 | 0.7652 (4) | 0.5926 (3) | 0.3581 (4) | 0.0605 (13) | |
H4 | 0.8185 | 0.6481 | 0.3907 | 0.073* | |
C5 | 0.6720 (4) | 0.6039 (4) | 0.2970 (4) | 0.0671 (15) | |
H5 | 0.6624 | 0.6669 | 0.2872 | 0.081* | |
C6 | 0.5950 (4) | 0.5224 (4) | 0.2515 (4) | 0.0551 (12) | |
H6 | 0.5322 | 0.5310 | 0.2114 | 0.066* | |
C7 | 0.5187 (3) | 0.3435 (3) | 0.2097 (3) | 0.0449 (11) | |
H7 | 0.4630 | 0.3587 | 0.1641 | 0.054* | |
C8 | 0.4112 (3) | 0.1850 (4) | 0.1596 (3) | 0.0525 (12) | |
H8A | 0.3901 | 0.1941 | 0.0901 | 0.063* | |
H8B | 0.3585 | 0.1999 | 0.1903 | 0.063* | |
C9 | 0.4223 (3) | 0.0790 (4) | 0.1584 (3) | 0.0541 (12) | |
H9A | 0.3551 | 0.0343 | 0.1299 | 0.065* | |
H9B | 0.4645 | 0.0598 | 0.1162 | 0.065* | |
C10 | 0.4816 (3) | −0.0326 (3) | 0.2721 (4) | 0.0584 (13) | |
H10A | 0.5195 | −0.0312 | 0.3422 | 0.070* | |
H10B | 0.5223 | −0.0553 | 0.2295 | 0.070* | |
C11 | 0.3812 (4) | −0.1081 (4) | 0.2408 (4) | 0.0739 (16) | |
H11A | 0.3360 | −0.0821 | 0.2752 | 0.111* | |
H11B | 0.3943 | −0.1696 | 0.2591 | 0.111* | |
H11C | 0.3494 | −0.1205 | 0.1681 | 0.111* | |
C12 | 0.7412 (3) | 0.0032 (3) | 0.3050 (3) | 0.0362 (9) | |
C13 | 0.7125 (3) | 0.0398 (3) | 0.2158 (3) | 0.0332 (9) | |
C14 | 0.7277 (3) | −0.0116 (3) | 0.1278 (3) | 0.0415 (10) | |
H14 | 0.7111 | 0.0127 | 0.0687 | 0.050* | |
C15 | 0.7669 (3) | −0.0979 (3) | 0.1261 (3) | 0.0489 (11) | |
H15 | 0.7757 | −0.1311 | 0.0662 | 0.059* | |
C16 | 0.7929 (3) | −0.1350 (3) | 0.2126 (4) | 0.0550 (12) | |
H16 | 0.8192 | −0.1931 | 0.2115 | 0.066* | |
C17 | 0.7794 (3) | −0.0854 (3) | 0.3003 (3) | 0.0472 (11) | |
H17 | 0.7961 | −0.1112 | 0.3585 | 0.057* | |
C18 | 0.7349 (3) | 0.0516 (3) | 0.4028 (3) | 0.0392 (9) | |
H18 | 0.7650 | 0.0265 | 0.4589 | 0.047* | |
C19 | 0.6878 (4) | 0.1582 (3) | 0.5232 (3) | 0.0504 (11) | |
H19A | 0.6386 | 0.1089 | 0.5364 | 0.060* | |
H19B | 0.7549 | 0.1637 | 0.5720 | 0.060* | |
C20 | 0.6577 (4) | 0.2546 (4) | 0.5359 (3) | 0.0647 (14) | |
H20A | 0.7136 | 0.3066 | 0.5373 | 0.078* | |
H20B | 0.6435 | 0.2700 | 0.6005 | 0.078* | |
C21 | 0.5319 (4) | 0.3480 (4) | 0.4615 (4) | 0.0654 (14) | |
H21A | 0.4746 | 0.3448 | 0.4014 | 0.078* | |
H21B | 0.5881 | 0.4000 | 0.4631 | 0.078* | |
C22 | 0.4996 (4) | 0.3783 (4) | 0.5559 (4) | 0.0725 (15) | |
H22A | 0.4529 | 0.3228 | 0.5619 | 0.109* | |
H22B | 0.4661 | 0.4340 | 0.5501 | 0.109* | |
H22C | 0.5594 | 0.3974 | 0.6156 | 0.109* | |
C23 | 0.6872 (3) | 0.3637 (3) | 0.0586 (3) | 0.0391 (9) | |
C24 | 0.6747 (3) | 0.2616 (3) | 0.0610 (3) | 0.0343 (9) | |
C25 | 0.5815 (3) | 0.1981 (3) | 0.0045 (3) | 0.0433 (10) | |
H25 | 0.5728 | 0.1303 | 0.0048 | 0.052* | |
C26 | 0.5012 (3) | 0.2329 (4) | −0.0522 (3) | 0.0544 (12) | |
H26 | 0.4394 | 0.1885 | −0.0902 | 0.065* | |
C27 | 0.5121 (4) | 0.3327 (4) | −0.0529 (4) | 0.0616 (14) | |
H27 | 0.4575 | 0.3565 | −0.0901 | 0.074* | |
C28 | 0.6033 (3) | 0.3968 (4) | 0.0014 (3) | 0.0541 (12) | |
H28 | 0.6102 | 0.4643 | 0.0004 | 0.065* | |
C29 | 0.7811 (3) | 0.4382 (3) | 0.1130 (3) | 0.0440 (10) | |
H29 | 0.7777 | 0.5049 | 0.1139 | 0.053* | |
C30 | 0.9556 (4) | 0.5064 (3) | 0.2028 (4) | 0.0635 (14) | |
H30A | 0.9328 | 0.5644 | 0.2321 | 0.076* | |
H30B | 0.9819 | 0.5225 | 0.1487 | 0.076* | |
C31 | 1.0381 (4) | 0.4832 (4) | 0.2823 (4) | 0.0721 (15) | |
H31A | 1.1000 | 0.5347 | 0.3004 | 0.086* | |
H31B | 1.0173 | 0.4827 | 0.3431 | 0.086* | |
C32 | 1.1361 (3) | 0.3596 (4) | 0.3290 (4) | 0.0687 (15) | |
H32A | 1.1420 | 0.2910 | 0.3057 | 0.082* | |
H32B | 1.1104 | 0.3617 | 0.3870 | 0.082* | |
C33 | 1.2419 (4) | 0.4255 (4) | 0.3648 (4) | 0.0821 (18) | |
H33A | 1.2653 | 0.4304 | 0.3069 | 0.123* | |
H33B | 1.2886 | 0.3971 | 0.4110 | 0.123* | |
H33C | 1.2395 | 0.4911 | 0.3992 | 0.123* | |
C34 | 0.9668 (3) | 0.1726 (3) | 0.3815 (3) | 0.0389 (9) | |
C35 | 0.9259 (3) | 0.2594 (3) | 0.3990 (3) | 0.0356 (9) | |
C36 | 0.9243 (3) | 0.2973 (3) | 0.4978 (3) | 0.0448 (10) | |
H36 | 0.9000 | 0.3558 | 0.5113 | 0.054* | |
C37 | 0.9575 (3) | 0.2503 (4) | 0.5755 (3) | 0.0518 (12) | |
H37 | 0.9552 | 0.2771 | 0.6405 | 0.062* | |
C38 | 0.9943 (4) | 0.1637 (4) | 0.5584 (4) | 0.0557 (12) | |
H38 | 1.0148 | 0.1306 | 0.6105 | 0.067* | |
C39 | 1.0000 (3) | 0.1273 (3) | 0.4620 (3) | 0.0480 (11) | |
H39 | 1.0272 | 0.0703 | 0.4508 | 0.058* | |
C40 | 0.9753 (3) | 0.1271 (3) | 0.2836 (3) | 0.0426 (10) | |
H40 | 0.9979 | 0.0669 | 0.2792 | 0.051* | |
C41 | 0.9763 (4) | 0.1066 (3) | 0.1129 (4) | 0.0577 (13) | |
H41A | 0.9580 | 0.0349 | 0.1066 | 0.069* | |
H41B | 1.0492 | 0.1242 | 0.1210 | 0.069* | |
C42 | 0.9151 (4) | 0.1334 (3) | 0.0186 (3) | 0.0566 (13) | |
H42A | 0.9362 | 0.1056 | −0.0393 | 0.068* | |
H42B | 0.8424 | 0.1057 | 0.0037 | 0.068* | |
C43 | 0.8728 (4) | 0.2776 (4) | −0.0532 (3) | 0.0604 (13) | |
H43A | 0.8859 | 0.3503 | −0.0355 | 0.073* | |
H43B | 0.8000 | 0.2533 | −0.0646 | 0.073* | |
C44 | 0.8958 (4) | 0.2445 (5) | −0.1526 (4) | 0.0851 (19) | |
H44A | 0.9683 | 0.2646 | −0.1415 | 0.128* | |
H44B | 0.8583 | 0.2750 | −0.2035 | 0.128* | |
H44C | 0.8754 | 0.1728 | −0.1755 | 0.128* | |
H8 | 0.9993 (13) | 0.265 (4) | 0.042 (4) | 0.080* | |
H2 | 0.426 (3) | 0.080 (4) | 0.298 (3) | 0.080* | |
H6A | 1.082 (4) | 0.398 (4) | 0.194 (3) | 0.080* | |
H4A | 0.518 (3) | 0.203 (3) | 0.455 (4) | 0.080* | |
H3A | 0.730 (4) | 0.190 (3) | 0.154 (3) | 0.080* | |
H1 | 0.7755 (19) | 0.316 (4) | 0.333 (4) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0329 (3) | 0.0372 (3) | 0.0311 (3) | 0.0083 (2) | 0.0110 (2) | 0.0111 (2) |
Ni2 | 0.0338 (3) | 0.0336 (3) | 0.0348 (3) | 0.0044 (2) | 0.0124 (2) | 0.0070 (2) |
Cl1 | 0.0968 (12) | 0.0888 (11) | 0.1418 (15) | 0.0513 (10) | 0.0861 (12) | 0.0712 (11) |
Cl2 | 0.0591 (8) | 0.0723 (9) | 0.0889 (10) | 0.0243 (7) | 0.0416 (8) | 0.0402 (8) |
O1 | 0.0324 (15) | 0.0366 (15) | 0.0491 (17) | 0.0135 (12) | 0.0135 (13) | 0.0145 (13) |
O2 | 0.0431 (16) | 0.0347 (15) | 0.0352 (15) | 0.0141 (12) | 0.0151 (12) | 0.0155 (12) |
O3 | 0.0350 (15) | 0.0365 (15) | 0.0397 (16) | 0.0055 (12) | 0.0117 (12) | 0.0187 (12) |
O4 | 0.0380 (15) | 0.0412 (15) | 0.0344 (15) | 0.0168 (12) | 0.0132 (12) | 0.0130 (12) |
O5 | 0.079 (3) | 0.101 (3) | 0.167 (5) | 0.036 (3) | 0.064 (3) | 0.053 (3) |
O6 | 0.093 (3) | 0.101 (4) | 0.149 (5) | 0.030 (3) | 0.005 (3) | 0.038 (3) |
O7 | 0.145 (5) | 0.129 (4) | 0.219 (6) | 0.061 (4) | 0.122 (5) | 0.035 (4) |
O8 | 0.212 (6) | 0.230 (6) | 0.219 (6) | 0.120 (5) | 0.149 (5) | 0.175 (5) |
O9 | 0.077 (5) | 0.177 (8) | 0.145 (8) | −0.011 (5) | 0.020 (5) | 0.039 (7) |
O10 | 0.065 (4) | 0.096 (5) | 0.134 (9) | 0.037 (4) | 0.030 (5) | 0.056 (5) |
O12 | 0.252 (18) | 0.075 (6) | 0.180 (9) | 0.063 (8) | 0.183 (11) | 0.051 (6) |
O9' | 0.040 (6) | 0.18 (2) | 0.23 (2) | 0.026 (8) | 0.042 (9) | 0.152 (19) |
O12' | 0.132 (11) | 0.092 (9) | 0.090 (6) | 0.033 (8) | 0.044 (7) | 0.022 (6) |
O10' | 0.17 (2) | 0.117 (13) | 0.100 (15) | 0.092 (16) | 0.079 (16) | 0.041 (11) |
O11 | 0.097 (3) | 0.114 (3) | 0.179 (5) | 0.044 (3) | 0.081 (3) | 0.105 (3) |
N1 | 0.0325 (18) | 0.050 (2) | 0.0349 (19) | 0.0097 (16) | 0.0099 (15) | 0.0130 (16) |
N2 | 0.041 (2) | 0.048 (2) | 0.041 (2) | 0.0023 (17) | 0.0157 (16) | 0.0115 (17) |
N3 | 0.0418 (19) | 0.0352 (18) | 0.0314 (18) | 0.0098 (15) | 0.0125 (15) | 0.0098 (14) |
N4 | 0.045 (2) | 0.052 (2) | 0.038 (2) | 0.0175 (17) | 0.0156 (17) | 0.0111 (17) |
N5 | 0.042 (2) | 0.0350 (19) | 0.043 (2) | 0.0004 (16) | 0.0102 (17) | 0.0118 (16) |
N6 | 0.0354 (19) | 0.043 (2) | 0.046 (2) | 0.0034 (16) | 0.0121 (17) | 0.0057 (17) |
N7 | 0.0389 (19) | 0.0358 (19) | 0.048 (2) | 0.0079 (15) | 0.0197 (17) | 0.0059 (16) |
N8 | 0.044 (2) | 0.048 (2) | 0.045 (2) | −0.0002 (17) | 0.0214 (18) | 0.0031 (17) |
C1 | 0.046 (2) | 0.047 (2) | 0.043 (2) | 0.021 (2) | 0.021 (2) | 0.020 (2) |
C2 | 0.042 (2) | 0.036 (2) | 0.041 (2) | 0.0151 (19) | 0.0212 (19) | 0.0141 (18) |
C3 | 0.051 (3) | 0.046 (3) | 0.054 (3) | 0.014 (2) | 0.018 (2) | 0.011 (2) |
C4 | 0.070 (3) | 0.039 (3) | 0.077 (4) | 0.010 (2) | 0.030 (3) | 0.014 (2) |
C5 | 0.095 (4) | 0.042 (3) | 0.086 (4) | 0.029 (3) | 0.044 (3) | 0.029 (3) |
C6 | 0.066 (3) | 0.060 (3) | 0.055 (3) | 0.033 (3) | 0.023 (3) | 0.030 (2) |
C7 | 0.044 (3) | 0.063 (3) | 0.040 (2) | 0.025 (2) | 0.018 (2) | 0.025 (2) |
C8 | 0.035 (2) | 0.077 (3) | 0.042 (3) | 0.007 (2) | 0.004 (2) | 0.021 (2) |
C9 | 0.046 (3) | 0.066 (3) | 0.037 (3) | −0.006 (2) | 0.005 (2) | 0.005 (2) |
C10 | 0.050 (3) | 0.047 (3) | 0.070 (3) | −0.005 (2) | 0.016 (2) | 0.010 (2) |
C11 | 0.074 (4) | 0.065 (3) | 0.073 (4) | −0.016 (3) | 0.029 (3) | 0.010 (3) |
C12 | 0.034 (2) | 0.036 (2) | 0.040 (2) | 0.0090 (17) | 0.0105 (18) | 0.0132 (18) |
C13 | 0.029 (2) | 0.031 (2) | 0.039 (2) | 0.0029 (16) | 0.0122 (17) | 0.0074 (17) |
C14 | 0.042 (2) | 0.040 (2) | 0.040 (2) | 0.0034 (19) | 0.0115 (19) | 0.0059 (19) |
C15 | 0.044 (3) | 0.046 (3) | 0.050 (3) | 0.009 (2) | 0.013 (2) | −0.003 (2) |
C16 | 0.054 (3) | 0.044 (3) | 0.065 (3) | 0.023 (2) | 0.012 (2) | 0.006 (2) |
C17 | 0.048 (3) | 0.042 (2) | 0.054 (3) | 0.018 (2) | 0.010 (2) | 0.020 (2) |
C18 | 0.044 (2) | 0.040 (2) | 0.038 (2) | 0.0111 (19) | 0.0133 (19) | 0.0180 (19) |
C19 | 0.061 (3) | 0.060 (3) | 0.035 (2) | 0.022 (2) | 0.015 (2) | 0.015 (2) |
C20 | 0.082 (4) | 0.072 (3) | 0.042 (3) | 0.024 (3) | 0.021 (3) | 0.010 (3) |
C21 | 0.087 (4) | 0.060 (3) | 0.060 (3) | 0.026 (3) | 0.037 (3) | 0.008 (3) |
C22 | 0.090 (4) | 0.075 (4) | 0.072 (4) | 0.038 (3) | 0.047 (3) | 0.016 (3) |
C23 | 0.037 (2) | 0.044 (2) | 0.040 (2) | 0.0083 (19) | 0.0119 (19) | 0.0203 (19) |
C24 | 0.034 (2) | 0.041 (2) | 0.032 (2) | 0.0085 (18) | 0.0137 (17) | 0.0133 (17) |
C25 | 0.042 (2) | 0.046 (2) | 0.042 (2) | 0.004 (2) | 0.014 (2) | 0.012 (2) |
C26 | 0.041 (3) | 0.071 (3) | 0.048 (3) | 0.002 (2) | 0.008 (2) | 0.021 (2) |
C27 | 0.044 (3) | 0.080 (4) | 0.064 (3) | 0.018 (3) | 0.008 (2) | 0.038 (3) |
C28 | 0.052 (3) | 0.058 (3) | 0.056 (3) | 0.014 (2) | 0.012 (2) | 0.030 (2) |
C29 | 0.058 (3) | 0.033 (2) | 0.047 (3) | 0.010 (2) | 0.020 (2) | 0.0180 (19) |
C30 | 0.060 (3) | 0.036 (3) | 0.077 (4) | −0.002 (2) | −0.001 (3) | 0.013 (2) |
C31 | 0.063 (3) | 0.051 (3) | 0.084 (4) | 0.003 (3) | 0.006 (3) | 0.005 (3) |
C32 | 0.043 (3) | 0.073 (4) | 0.075 (4) | −0.007 (3) | 0.000 (3) | 0.023 (3) |
C33 | 0.050 (3) | 0.086 (4) | 0.090 (4) | −0.004 (3) | −0.002 (3) | 0.022 (3) |
C34 | 0.032 (2) | 0.039 (2) | 0.048 (3) | 0.0071 (18) | 0.0121 (19) | 0.0157 (19) |
C35 | 0.026 (2) | 0.040 (2) | 0.040 (2) | 0.0051 (17) | 0.0071 (17) | 0.0125 (18) |
C36 | 0.044 (2) | 0.051 (3) | 0.040 (2) | 0.017 (2) | 0.010 (2) | 0.011 (2) |
C37 | 0.047 (3) | 0.065 (3) | 0.036 (2) | 0.007 (2) | 0.006 (2) | 0.008 (2) |
C38 | 0.056 (3) | 0.059 (3) | 0.052 (3) | 0.014 (2) | 0.006 (2) | 0.029 (2) |
C39 | 0.042 (2) | 0.045 (3) | 0.059 (3) | 0.017 (2) | 0.010 (2) | 0.021 (2) |
C40 | 0.035 (2) | 0.035 (2) | 0.063 (3) | 0.0145 (18) | 0.020 (2) | 0.011 (2) |
C41 | 0.068 (3) | 0.051 (3) | 0.064 (3) | 0.018 (2) | 0.037 (3) | 0.005 (2) |
C42 | 0.065 (3) | 0.053 (3) | 0.050 (3) | 0.003 (2) | 0.030 (3) | −0.004 (2) |
C43 | 0.061 (3) | 0.076 (4) | 0.038 (3) | −0.003 (3) | 0.017 (2) | 0.010 (2) |
C44 | 0.089 (4) | 0.115 (5) | 0.047 (3) | −0.004 (4) | 0.032 (3) | 0.012 (3) |
Geometric parameters (Å, º) top
Ni1—N3 | 2.031 (3) | C11—H11C | 0.9600 |
Ni1—N1 | 2.037 (3) | C12—C17 | 1.403 (5) |
Ni1—O2 | 2.110 (3) | C12—C13 | 1.407 (5) |
Ni1—O1 | 2.134 (3) | C12—C18 | 1.444 (5) |
Ni1—N2 | 2.146 (4) | C13—C14 | 1.393 (5) |
Ni1—N4 | 2.150 (3) | C14—C15 | 1.382 (6) |
Ni2—N5 | 2.022 (3) | C14—H14 | 0.9300 |
Ni2—N7 | 2.031 (3) | C15—C16 | 1.374 (6) |
Ni2—O4 | 2.098 (3) | C15—H15 | 0.9300 |
Ni2—O3 | 2.114 (3) | C16—C17 | 1.369 (6) |
Ni2—N6 | 2.146 (3) | C16—H16 | 0.9300 |
Ni2—N8 | 2.153 (3) | C17—H17 | 0.9300 |
Cl1—O8 | 1.369 (5) | C18—H18 | 0.9300 |
Cl1—O6 | 1.397 (5) | C19—C20 | 1.451 (6) |
Cl1—O7 | 1.414 (5) | C19—H19A | 0.9700 |
Cl1—O5 | 1.420 (4) | C19—H19B | 0.9700 |
Cl2—O9' | 1.347 (8) | C20—H20A | 0.9700 |
Cl2—O12 | 1.372 (5) | C20—H20B | 0.9700 |
Cl2—O10 | 1.385 (6) | C21—C22 | 1.518 (6) |
Cl2—O10' | 1.394 (9) | C21—H21A | 0.9700 |
Cl2—O11 | 1.408 (3) | C21—H21B | 0.9700 |
Cl2—O9 | 1.430 (7) | C22—H22A | 0.9600 |
Cl2—O12' | 1.454 (9) | C22—H22B | 0.9600 |
O1—C2 | 1.358 (4) | C22—H22C | 0.9600 |
O1—H1 | 0.86 (3) | C23—C28 | 1.401 (5) |
O2—C13 | 1.338 (4) | C23—C24 | 1.408 (5) |
O3—C24 | 1.346 (4) | C23—C29 | 1.451 (6) |
O3—H3A | 0.84 (4) | C24—C25 | 1.382 (5) |
O4—C35 | 1.334 (4) | C25—C26 | 1.376 (6) |
N1—C7 | 1.270 (5) | C25—H25 | 0.9300 |
N1—C8 | 1.459 (5) | C26—C27 | 1.371 (6) |
N2—C9 | 1.480 (5) | C26—H26 | 0.9300 |
N2—C10 | 1.481 (6) | C27—C28 | 1.361 (6) |
N2—H2 | 0.89 (4) | C27—H27 | 0.9300 |
N3—C18 | 1.274 (5) | C28—H28 | 0.9300 |
N3—C19 | 1.461 (5) | C29—H29 | 0.9300 |
N4—C21 | 1.456 (6) | C30—C31 | 1.473 (7) |
N4—C20 | 1.482 (6) | C30—H30A | 0.9700 |
N4—H4A | 0.89 (4) | C30—H30B | 0.9700 |
N5—C29 | 1.280 (5) | C31—H31A | 0.9700 |
N5—C30 | 1.464 (5) | C31—H31B | 0.9700 |
N6—C31 | 1.454 (6) | C32—C33 | 1.503 (6) |
N6—C32 | 1.473 (6) | C32—H32A | 0.9700 |
N6—H6A | 0.90 (5) | C32—H32B | 0.9700 |
N7—C40 | 1.274 (5) | C33—H33A | 0.9600 |
N7—C41 | 1.467 (5) | C33—H33B | 0.9600 |
N8—C42 | 1.469 (6) | C33—H33C | 0.9600 |
N8—C43 | 1.479 (6) | C34—C39 | 1.385 (6) |
N8—H8 | 0.90 (3) | C34—C35 | 1.414 (5) |
C1—C6 | 1.396 (6) | C34—C40 | 1.446 (6) |
C1—C2 | 1.399 (5) | C35—C36 | 1.395 (5) |
C1—C7 | 1.445 (6) | C36—C37 | 1.369 (6) |
C2—C3 | 1.382 (6) | C36—H36 | 0.9300 |
C3—C4 | 1.377 (6) | C37—C38 | 1.378 (6) |
C3—H3 | 0.9300 | C37—H37 | 0.9300 |
C4—C5 | 1.380 (7) | C38—C39 | 1.379 (6) |
C4—H4 | 0.9300 | C38—H38 | 0.9300 |
C5—C6 | 1.351 (7) | C39—H39 | 0.9300 |
C5—H5 | 0.9300 | C40—H40 | 0.9300 |
C6—H6 | 0.9300 | C41—C42 | 1.496 (6) |
C7—H7 | 0.9300 | C41—H41A | 0.9700 |
C8—C9 | 1.497 (6) | C41—H41B | 0.9700 |
C8—H8A | 0.9700 | C42—H42A | 0.9700 |
C8—H8B | 0.9700 | C42—H42B | 0.9700 |
C9—H9A | 0.9700 | C43—C44 | 1.518 (6) |
C9—H9B | 0.9700 | C43—H43A | 0.9700 |
C10—C11 | 1.511 (6) | C43—H43B | 0.9700 |
C10—H10A | 0.9700 | C44—H44A | 0.9600 |
C10—H10B | 0.9700 | C44—H44B | 0.9600 |
C11—H11A | 0.9600 | C44—H44C | 0.9600 |
C11—H11B | 0.9600 | | |
| | | |
N3—Ni1—N1 | 176.64 (12) | H11A—C11—H11B | 109.5 |
N3—Ni1—O2 | 84.89 (11) | C10—C11—H11C | 109.5 |
N1—Ni1—O2 | 97.26 (11) | H11A—C11—H11C | 109.5 |
N3—Ni1—O1 | 98.53 (12) | H11B—C11—H11C | 109.5 |
N1—Ni1—O1 | 84.27 (12) | C17—C12—C13 | 118.8 (4) |
O2—Ni1—O1 | 84.79 (10) | C17—C12—C18 | 117.0 (4) |
N3—Ni1—N2 | 95.92 (14) | C13—C12—C18 | 124.1 (3) |
N1—Ni1—N2 | 81.40 (14) | O2—C13—C14 | 120.2 (3) |
O2—Ni1—N2 | 93.31 (12) | O2—C13—C12 | 121.8 (3) |
O1—Ni1—N2 | 165.19 (12) | C14—C13—C12 | 118.1 (4) |
N3—Ni1—N4 | 81.40 (13) | C15—C14—C13 | 121.6 (4) |
N1—Ni1—N4 | 96.64 (13) | C15—C14—H14 | 119.2 |
O2—Ni1—N4 | 165.62 (12) | C13—C14—H14 | 119.2 |
O1—Ni1—N4 | 92.94 (13) | C16—C15—C14 | 120.4 (4) |
N2—Ni1—N4 | 92.41 (14) | C16—C15—H15 | 119.8 |
N5—Ni2—N7 | 178.45 (12) | C14—C15—H15 | 119.8 |
N5—Ni2—O4 | 94.04 (12) | C17—C16—C15 | 119.2 (4) |
N7—Ni2—O4 | 86.61 (12) | C17—C16—H16 | 120.4 |
N5—Ni2—O3 | 85.69 (12) | C15—C16—H16 | 120.4 |
N7—Ni2—O3 | 95.75 (12) | C16—C17—C12 | 121.9 (4) |
O4—Ni2—O3 | 86.69 (10) | C16—C17—H17 | 119.1 |
N5—Ni2—N6 | 82.08 (14) | C12—C17—H17 | 119.1 |
N7—Ni2—N6 | 96.50 (14) | N3—C18—C12 | 125.9 (4) |
O4—Ni2—N6 | 91.87 (12) | N3—C18—H18 | 117.0 |
O3—Ni2—N6 | 167.56 (12) | C12—C18—H18 | 117.0 |
N5—Ni2—N8 | 97.46 (14) | C20—C19—N3 | 110.4 (4) |
N7—Ni2—N8 | 81.97 (14) | C20—C19—H19A | 109.6 |
O4—Ni2—N8 | 167.99 (12) | N3—C19—H19A | 109.6 |
O3—Ni2—N8 | 90.74 (12) | C20—C19—H19B | 109.6 |
N6—Ni2—N8 | 93.11 (13) | N3—C19—H19B | 109.6 |
O8—Cl1—O6 | 113.6 (4) | H19A—C19—H19B | 108.1 |
O8—Cl1—O7 | 108.2 (4) | C19—C20—N4 | 110.2 (4) |
O6—Cl1—O7 | 107.1 (3) | C19—C20—H20A | 109.6 |
O8—Cl1—O5 | 107.8 (3) | N4—C20—H20A | 109.6 |
O6—Cl1—O5 | 109.0 (3) | C19—C20—H20B | 109.6 |
O7—Cl1—O5 | 111.2 (3) | N4—C20—H20B | 109.6 |
O9'—Cl2—O12 | 67.8 (9) | H20A—C20—H20B | 108.1 |
O9'—Cl2—O10 | 128.6 (11) | N4—C21—C22 | 115.0 (4) |
O12—Cl2—O10 | 115.0 (6) | N4—C21—H21A | 108.5 |
O9'—Cl2—O10' | 113.4 (9) | C22—C21—H21A | 108.5 |
O12—Cl2—O10' | 130.0 (9) | N4—C21—H21B | 108.5 |
O9'—Cl2—O11 | 115.6 (7) | C22—C21—H21B | 108.5 |
O12—Cl2—O11 | 112.7 (4) | H21A—C21—H21B | 107.5 |
O10—Cl2—O11 | 109.8 (5) | C21—C22—H22A | 109.5 |
O10'—Cl2—O11 | 110.5 (9) | C21—C22—H22B | 109.5 |
O12—Cl2—O9 | 105.8 (6) | H22A—C22—H22B | 109.5 |
O10—Cl2—O9 | 106.8 (6) | C21—C22—H22C | 109.5 |
O10'—Cl2—O9 | 84.8 (12) | H22A—C22—H22C | 109.5 |
O11—Cl2—O9 | 106.1 (5) | H22B—C22—H22C | 109.5 |
O9'—Cl2—O12' | 107.5 (8) | C28—C23—C24 | 118.3 (4) |
O10—Cl2—O12' | 82.8 (9) | C28—C23—C29 | 117.3 (4) |
O10'—Cl2—O12' | 104.8 (8) | C24—C23—C29 | 124.4 (4) |
O11—Cl2—O12' | 103.9 (7) | O3—C24—C25 | 120.0 (4) |
O9—Cl2—O12' | 142.7 (7) | O3—C24—C23 | 121.5 (3) |
C2—O1—Ni1 | 128.4 (2) | C25—C24—C23 | 118.5 (4) |
C2—O1—H1 | 110 (3) | C26—C25—C24 | 121.6 (4) |
Ni1—O1—H1 | 118 (3) | C26—C25—H25 | 119.2 |
C13—O2—Ni1 | 127.6 (2) | C24—C25—H25 | 119.2 |
C24—O3—Ni2 | 129.0 (2) | C27—C26—C25 | 120.1 (4) |
C24—O3—H3A | 112 (3) | C27—C26—H26 | 120.0 |
Ni2—O3—H3A | 112 (3) | C25—C26—H26 | 120.0 |
C35—O4—Ni2 | 128.0 (2) | C28—C27—C26 | 119.6 (4) |
C7—N1—C8 | 117.2 (4) | C28—C27—H27 | 120.2 |
C7—N1—Ni1 | 129.1 (3) | C26—C27—H27 | 120.2 |
C8—N1—Ni1 | 113.1 (3) | C27—C28—C23 | 121.9 (4) |
C9—N2—C10 | 113.1 (4) | C27—C28—H28 | 119.1 |
C9—N2—Ni1 | 102.8 (2) | C23—C28—H28 | 119.1 |
C10—N2—Ni1 | 120.4 (3) | N5—C29—C23 | 126.1 (4) |
C9—N2—H2 | 107 (3) | N5—C29—H29 | 116.9 |
C10—N2—H2 | 100 (3) | C23—C29—H29 | 116.9 |
Ni1—N2—H2 | 113 (3) | N5—C30—C31 | 110.6 (4) |
C18—N3—C19 | 116.9 (3) | N5—C30—H30A | 109.5 |
C18—N3—Ni1 | 129.4 (3) | C31—C30—H30A | 109.5 |
C19—N3—Ni1 | 112.7 (2) | N5—C30—H30B | 109.5 |
C21—N4—C20 | 111.6 (4) | C31—C30—H30B | 109.5 |
C21—N4—Ni1 | 121.1 (3) | H30A—C30—H30B | 108.1 |
C20—N4—Ni1 | 102.7 (3) | N6—C31—C30 | 110.8 (4) |
C21—N4—H4A | 112 (3) | N6—C31—H31A | 109.5 |
C20—N4—H4A | 103 (3) | C30—C31—H31A | 109.5 |
Ni1—N4—H4A | 104 (3) | N6—C31—H31B | 109.5 |
C29—N5—C30 | 117.3 (4) | C30—C31—H31B | 109.5 |
C29—N5—Ni2 | 130.5 (3) | H31A—C31—H31B | 108.1 |
C30—N5—Ni2 | 112.2 (3) | N6—C32—C33 | 115.4 (4) |
C31—N6—C32 | 110.4 (4) | N6—C32—H32A | 108.4 |
C31—N6—Ni2 | 103.3 (3) | C33—C32—H32A | 108.4 |
C32—N6—Ni2 | 118.6 (3) | N6—C32—H32B | 108.4 |
C31—N6—H6A | 100 (3) | C33—C32—H32B | 108.4 |
C32—N6—H6A | 115 (3) | H32A—C32—H32B | 107.5 |
Ni2—N6—H6A | 107 (3) | C32—C33—H33A | 109.5 |
C40—N7—C41 | 118.4 (4) | C32—C33—H33B | 109.5 |
C40—N7—Ni2 | 129.0 (3) | H33A—C33—H33B | 109.5 |
C41—N7—Ni2 | 112.3 (3) | C32—C33—H33C | 109.5 |
C42—N8—C43 | 113.3 (4) | H33A—C33—H33C | 109.5 |
C42—N8—Ni2 | 103.5 (3) | H33B—C33—H33C | 109.5 |
C43—N8—Ni2 | 118.5 (3) | C39—C34—C35 | 118.6 (4) |
C42—N8—H8 | 107 (3) | C39—C34—C40 | 117.6 (4) |
C43—N8—H8 | 106 (3) | C35—C34—C40 | 123.7 (4) |
Ni2—N8—H8 | 108 (3) | O4—C35—C36 | 119.2 (4) |
C6—C1—C2 | 117.7 (4) | O4—C35—C34 | 122.7 (4) |
C6—C1—C7 | 118.5 (4) | C36—C35—C34 | 118.1 (4) |
C2—C1—C7 | 123.8 (4) | C37—C36—C35 | 121.6 (4) |
O1—C2—C3 | 120.1 (4) | C37—C36—H36 | 119.2 |
O1—C2—C1 | 120.8 (4) | C35—C36—H36 | 119.2 |
C3—C2—C1 | 119.1 (4) | C36—C37—C38 | 120.7 (4) |
C4—C3—C2 | 121.6 (4) | C36—C37—H37 | 119.6 |
C4—C3—H3 | 119.2 | C38—C37—H37 | 119.6 |
C2—C3—H3 | 119.2 | C37—C38—C39 | 118.5 (4) |
C3—C4—C5 | 119.5 (5) | C37—C38—H38 | 120.8 |
C3—C4—H4 | 120.3 | C39—C38—H38 | 120.8 |
C5—C4—H4 | 120.3 | C38—C39—C34 | 122.4 (4) |
C6—C5—C4 | 119.3 (4) | C38—C39—H39 | 118.8 |
C6—C5—H5 | 120.3 | C34—C39—H39 | 118.8 |
C4—C5—H5 | 120.3 | N7—C40—C34 | 127.0 (4) |
C5—C6—C1 | 122.8 (5) | N7—C40—H40 | 116.5 |
C5—C6—H6 | 118.6 | C34—C40—H40 | 116.5 |
C1—C6—H6 | 118.6 | N7—C41—C42 | 109.7 (4) |
N1—C7—C1 | 128.0 (4) | N7—C41—H41A | 109.7 |
N1—C7—H7 | 116.0 | C42—C41—H41A | 109.7 |
C1—C7—H7 | 116.0 | N7—C41—H41B | 109.7 |
N1—C8—C9 | 109.6 (3) | C42—C41—H41B | 109.7 |
N1—C8—H8A | 109.8 | H41A—C41—H41B | 108.2 |
C9—C8—H8A | 109.8 | N8—C42—C41 | 109.1 (4) |
N1—C8—H8B | 109.8 | N8—C42—H42A | 109.9 |
C9—C8—H8B | 109.8 | C41—C42—H42A | 109.9 |
H8A—C8—H8B | 108.2 | N8—C42—H42B | 109.9 |
N2—C9—C8 | 108.9 (4) | C41—C42—H42B | 109.9 |
N2—C9—H9A | 109.9 | H42A—C42—H42B | 108.3 |
C8—C9—H9A | 109.9 | N8—C43—C44 | 115.4 (4) |
N2—C9—H9B | 109.9 | N8—C43—H43A | 108.4 |
C8—C9—H9B | 109.9 | C44—C43—H43A | 108.4 |
H9A—C9—H9B | 108.3 | N8—C43—H43B | 108.4 |
N2—C10—C11 | 115.0 (4) | C44—C43—H43B | 108.4 |
N2—C10—H10A | 108.5 | H43A—C43—H43B | 107.5 |
C11—C10—H10A | 108.5 | C43—C44—H44A | 109.5 |
N2—C10—H10B | 108.5 | C43—C44—H44B | 109.5 |
C11—C10—H10B | 108.5 | H44A—C44—H44B | 109.5 |
H10A—C10—H10B | 107.5 | C43—C44—H44C | 109.5 |
C10—C11—H11A | 109.5 | H44A—C44—H44C | 109.5 |
C10—C11—H11B | 109.5 | H44B—C44—H44C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4 | 0.86 (3) | 1.60 (3) | 2.457 (4) | 180 (6) |
O3—H3A···O2 | 0.84 (4) | 1.61 (5) | 2.448 (3) | 172 (5) |
N4—H4A···O5 | 0.89 (4) | 2.37 (4) | 3.247 (6) | 167 (4) |
N6—H6A···O10i | 0.90 (5) | 2.52 (2) | 3.411 (13) | 174 (5) |
N6—H6A···O10′i | 0.90 (5) | 2.27 (2) | 3.16 (2) | 174 (5) |
N2—H2···Cl1 | 0.89 (4) | 2.92 (4) | 3.810 (4) | 177 (4) |
N2—H2···O8 | 0.89 (4) | 2.52 (3) | 3.316 (7) | 149 (4) |
N2—H2···O5 | 0.89 (4) | 2.36 (2) | 3.186 (6) | 154 (5) |
N8—H8···Cl2i | 0.90 (3) | 2.95 (3) | 3.837 (4) | 170 (4) |
N8—H8···O10i | 0.90 (3) | 2.57 (3) | 3.337 (10) | 143 (4) |
N8—H8···O11i | 0.90 (3) | 2.33 (2) | 3.202 (5) | 162 (5) |
C8—H8B···O8 | 0.97 | 2.50 | 3.325 (7) | 143 |
C18—H18···O6ii | 0.93 | 2.60 | 3.500 (7) | 163 (4) |
C29—H29···O12iii | 0.93 | 2.54 (3) | 3.410 (7) | 155 (4) |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y, z−1. |