In the title compound, [Ni(C5H10NO2S)(C6H18N4)]ClO4·2H2O, the NiII atom is in a slightly distorted octahedral coordination environment. Intermolecular hydrogen bonds link the cationic complexes into an extended two-dimensional network.
Supporting information
CCDC reference: 643019
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.068
- wR factor = 0.190
- Data-to-parameter ratio = 15.0
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT360_ALERT_2_B Short C(sp3)-C(sp3) Bond C8 - C9 ... 1.33 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D H2E .. H5D .. 1.42 Ang.
Alert level C
DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75
_refine_diff_density_max given = 2.419
Test value = 2.100
DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.39
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 2.42 e/A
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for Cl1
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker 1997); cell refinement: SAINT (Bruker, 1997; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
(dL-Methioninato-
κ2N,
O)(2,2',2''-triaminotriethylamine-
κ4N,
N',
N'',
N''')nickel(II) perchlorate
dihydrate
top
Crystal data top
[Ni(C5H10NO2S)(C6H18N4)]ClO4·2H2O | F(000) = 2064 |
Mr = 488.64 | Dx = 1.553 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9526 reflections |
a = 11.2597 (13) Å | θ = 1.8–26.1° |
b = 18.703 (2) Å | µ = 1.20 mm−1 |
c = 19.849 (2) Å | T = 293 K |
V = 4180.1 (8) Å3 | Block, purple |
Z = 8 | 0.20 × 0.10 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3670 independent reflections |
Radiation source: fine-focus sealed tube | 3199 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→12 |
Tmin = 0.810, Tmax = 0.879 | k = −21→22 |
21117 measured reflections | l = −23→23 |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0889P)2 + 16.6077P] where P = (Fo2 + 2Fc2)/3 |
3670 reflections | (Δ/σ)max = 0.010 |
244 parameters | Δρmax = 2.42 e Å−3 |
7 restraints | Δρmin = −1.01 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 | 0.78024 (5) | 0.49718 (3) | 0.66268 (3) | 0.0351 (3) | |
Cl1 | 0.75902 (14) | 0.60682 (9) | 0.41225 (8) | 0.0589 (4) | |
S1 | 1.03070 (19) | 0.68906 (10) | 0.85873 (12) | 0.0785 (6) | |
O1 | 0.6450 (3) | 0.51068 (18) | 0.73569 (19) | 0.0412 (8) | |
O2 | 0.5817 (3) | 0.5851 (2) | 0.8150 (2) | 0.0571 (11) | |
O3 | 0.7966 (12) | 0.6001 (5) | 0.4767 (4) | 0.186 (5) | |
O4 | 0.8602 (7) | 0.6163 (5) | 0.3729 (5) | 0.150 (3) | |
O5 | 0.7033 (6) | 0.5410 (4) | 0.3936 (4) | 0.114 (2) | |
O6 | 0.6872 (8) | 0.6638 (5) | 0.4035 (7) | 0.203 (6) | |
O1W | 0.9385 (9) | 0.1981 (5) | 0.9027 (5) | 0.176 (5) | |
H1E | 0.9059 | 0.2436 | 0.8931 | 0.264* | |
H1F | 0.9379 | 0.1666 | 0.8694 | 0.264* | |
O2W | 0.8244 (7) | 0.7064 (4) | 0.5788 (3) | 0.120 (2) | |
H2E | 0.8237 | 0.6783 | 0.6106 | 0.180* | |
H2F | 0.8233 | 0.6880 | 0.5412 | 0.180* | |
N1 | 0.6425 (4) | 0.5209 (3) | 0.5912 (2) | 0.0476 (11) | |
H1C | 0.5848 | 0.5466 | 0.6113 | 0.057* | |
H1D | 0.6724 | 0.5472 | 0.5572 | 0.057* | |
N2 | 0.8856 (4) | 0.4461 (2) | 0.7376 (2) | 0.0440 (10) | |
H2C | 0.9609 | 0.4620 | 0.7354 | 0.053* | |
H2D | 0.8567 | 0.4558 | 0.7788 | 0.053* | |
N3 | 0.9124 (4) | 0.4899 (3) | 0.5880 (2) | 0.0515 (12) | |
H3C | 0.9203 | 0.5322 | 0.5669 | 0.062* | |
H3D | 0.9825 | 0.4785 | 0.6069 | 0.062* | |
N4 | 0.7428 (4) | 0.3924 (2) | 0.6328 (2) | 0.0363 (9) | |
N5 | 0.8171 (4) | 0.5997 (2) | 0.6941 (3) | 0.0484 (11) | |
H5C | 0.8962 | 0.6054 | 0.6975 | 0.058* | |
H5D | 0.7899 | 0.6310 | 0.6633 | 0.058* | |
C1 | 0.5921 (5) | 0.4536 (3) | 0.5642 (3) | 0.0510 (14) | |
H1A | 0.6280 | 0.4428 | 0.5209 | 0.061* | |
H1B | 0.5072 | 0.4590 | 0.5576 | 0.061* | |
C2 | 0.6158 (5) | 0.3933 (3) | 0.6129 (3) | 0.0460 (13) | |
H2A | 0.5667 | 0.3993 | 0.6527 | 0.055* | |
H2B | 0.5951 | 0.3481 | 0.5921 | 0.055* | |
C3 | 0.8824 (5) | 0.3676 (3) | 0.7250 (3) | 0.0515 (14) | |
H3A | 0.8924 | 0.3420 | 0.7672 | 0.062* | |
H3B | 0.9468 | 0.3541 | 0.6951 | 0.062* | |
C4 | 0.7641 (5) | 0.3478 (3) | 0.6933 (3) | 0.0452 (12) | |
H4A | 0.7646 | 0.2977 | 0.6808 | 0.054* | |
H4B | 0.7007 | 0.3552 | 0.7256 | 0.054* | |
C5 | 0.8775 (6) | 0.4350 (4) | 0.5400 (3) | 0.0582 (16) | |
H5A | 0.9465 | 0.4193 | 0.5148 | 0.070* | |
H5B | 0.8205 | 0.4547 | 0.5083 | 0.070* | |
C6 | 0.8223 (5) | 0.3712 (3) | 0.5764 (3) | 0.0489 (13) | |
H6A | 0.7773 | 0.3431 | 0.5443 | 0.059* | |
H6B | 0.8854 | 0.3412 | 0.5940 | 0.059* | |
C7 | 0.6539 (4) | 0.5661 (3) | 0.7713 (3) | 0.0431 (12) | |
C8 | 0.7617 (6) | 0.6146 (4) | 0.7595 (4) | 0.074 (2) | |
H8A | 0.7257 | 0.6618 | 0.7528 | 0.089* | |
C9 | 0.8368 (8) | 0.6256 (5) | 0.8101 (4) | 0.084 (2) | |
H9A | 0.8931 | 0.5864 | 0.8119 | 0.101* | |
H9B | 0.7929 | 0.6260 | 0.8522 | 0.101* | |
C10 | 0.9089 (6) | 0.7004 (5) | 0.8026 (4) | 0.077 (2) | |
H10A | 0.8600 | 0.7407 | 0.8158 | 0.093* | |
H10B | 0.9361 | 0.7075 | 0.7567 | 0.093* | |
C11 | 0.9662 (8) | 0.7045 (5) | 0.9383 (4) | 0.088 (2) | |
H11A | 1.0256 | 0.6995 | 0.9727 | 0.133* | |
H11B | 0.9039 | 0.6703 | 0.9459 | 0.133* | |
H11C | 0.9338 | 0.7519 | 0.9397 | 0.133* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0275 (4) | 0.0325 (4) | 0.0454 (4) | −0.0025 (2) | 0.0027 (3) | 0.0001 (2) |
Cl1 | 0.0495 (8) | 0.0694 (10) | 0.0580 (9) | 0.0002 (7) | 0.0018 (7) | 0.0094 (7) |
S1 | 0.0688 (12) | 0.0580 (10) | 0.1087 (15) | 0.0142 (9) | 0.0242 (11) | 0.0153 (10) |
O1 | 0.0299 (18) | 0.0400 (19) | 0.054 (2) | −0.0093 (14) | 0.0057 (16) | −0.0058 (16) |
O2 | 0.035 (2) | 0.064 (3) | 0.072 (3) | −0.0074 (19) | 0.014 (2) | −0.019 (2) |
O3 | 0.302 (15) | 0.163 (8) | 0.092 (5) | −0.066 (9) | −0.060 (7) | 0.040 (5) |
O4 | 0.111 (6) | 0.130 (6) | 0.208 (9) | −0.016 (5) | 0.077 (6) | 0.004 (6) |
O5 | 0.097 (5) | 0.099 (5) | 0.146 (6) | −0.032 (4) | 0.006 (4) | −0.021 (4) |
O6 | 0.123 (7) | 0.116 (7) | 0.370 (17) | 0.052 (6) | −0.025 (9) | 0.030 (8) |
O1W | 0.180 (9) | 0.142 (7) | 0.206 (10) | 0.056 (6) | −0.088 (8) | −0.090 (7) |
O2W | 0.156 (7) | 0.109 (5) | 0.094 (5) | 0.001 (5) | 0.007 (5) | −0.001 (4) |
N1 | 0.045 (3) | 0.044 (2) | 0.054 (3) | 0.008 (2) | −0.003 (2) | 0.005 (2) |
N2 | 0.033 (2) | 0.045 (2) | 0.054 (3) | −0.0025 (19) | −0.006 (2) | −0.001 (2) |
N3 | 0.044 (3) | 0.051 (3) | 0.059 (3) | −0.006 (2) | 0.015 (2) | 0.003 (2) |
N4 | 0.035 (2) | 0.034 (2) | 0.041 (2) | −0.0008 (17) | 0.0023 (18) | 0.0011 (17) |
N5 | 0.037 (2) | 0.041 (2) | 0.067 (3) | −0.0112 (19) | 0.010 (2) | −0.007 (2) |
C1 | 0.041 (3) | 0.057 (3) | 0.054 (3) | 0.001 (3) | −0.012 (3) | 0.001 (3) |
C2 | 0.034 (3) | 0.047 (3) | 0.057 (3) | −0.008 (2) | −0.001 (2) | −0.004 (3) |
C3 | 0.052 (3) | 0.046 (3) | 0.057 (3) | 0.009 (3) | −0.009 (3) | 0.006 (3) |
C4 | 0.049 (3) | 0.035 (3) | 0.052 (3) | 0.000 (2) | −0.001 (3) | 0.005 (2) |
C5 | 0.055 (4) | 0.064 (4) | 0.056 (3) | −0.002 (3) | 0.024 (3) | 0.001 (3) |
C6 | 0.049 (3) | 0.044 (3) | 0.054 (3) | 0.006 (2) | 0.008 (3) | −0.008 (2) |
C7 | 0.029 (2) | 0.046 (3) | 0.054 (3) | −0.006 (2) | 0.004 (2) | −0.002 (2) |
C8 | 0.060 (4) | 0.072 (4) | 0.091 (5) | −0.039 (4) | 0.032 (4) | −0.041 (4) |
C9 | 0.082 (6) | 0.090 (6) | 0.080 (5) | −0.029 (5) | 0.003 (4) | −0.003 (4) |
C10 | 0.060 (4) | 0.102 (6) | 0.070 (4) | −0.039 (4) | 0.014 (4) | −0.036 (4) |
C11 | 0.090 (6) | 0.094 (6) | 0.081 (5) | −0.006 (5) | 0.004 (5) | 0.012 (5) |
Geometric parameters (Å, º) top
Ni1—N5 | 2.058 (4) | N5—C8 | 1.467 (8) |
Ni1—N4 | 2.090 (4) | N5—H5C | 0.9000 |
Ni1—N3 | 2.104 (5) | N5—H5D | 0.9000 |
Ni1—O1 | 2.117 (4) | C1—C2 | 1.510 (8) |
Ni1—N2 | 2.129 (4) | C1—H1A | 0.9700 |
Ni1—N1 | 2.149 (5) | C1—H1B | 0.9700 |
Cl1—O6 | 1.350 (7) | C2—H2A | 0.9700 |
Cl1—O3 | 1.354 (8) | C2—H2B | 0.9700 |
Cl1—O4 | 1.392 (7) | C3—C4 | 1.519 (8) |
Cl1—O5 | 1.431 (7) | C3—H3A | 0.9700 |
S1—C11 | 1.763 (9) | C3—H3B | 0.9700 |
S1—C10 | 1.780 (8) | C4—H4A | 0.9700 |
O1—C7 | 1.258 (6) | C4—H4B | 0.9700 |
O2—C7 | 1.240 (6) | C5—C6 | 1.527 (8) |
O1W—H1E | 0.9465 | C5—H5A | 0.9700 |
O1W—H1F | 0.8863 | C5—H5B | 0.9700 |
O2W—H2E | 0.8223 | C6—H6A | 0.9700 |
O2W—H2F | 0.8223 | C6—H6B | 0.9700 |
N1—C1 | 1.481 (8) | C7—C8 | 1.534 (8) |
N1—H1C | 0.9000 | C8—C9 | 1.328 (11) |
N1—H1D | 0.9000 | C8—H8A | 0.9800 |
N2—C3 | 1.489 (7) | C9—C10 | 1.624 (10) |
N2—H2C | 0.9000 | C9—H9A | 0.9700 |
N2—H2D | 0.9000 | C9—H9B | 0.9700 |
N3—C5 | 1.456 (8) | C10—H10A | 0.9700 |
N3—H3C | 0.9000 | C10—H10B | 0.9700 |
N3—H3D | 0.9000 | C11—H11A | 0.9600 |
N4—C4 | 1.483 (7) | C11—H11B | 0.9600 |
N4—C2 | 1.483 (7) | C11—H11C | 0.9600 |
N4—C6 | 1.487 (7) | | |
| | | |
N5—Ni1—N4 | 178.86 (18) | C2—C1—H1B | 109.7 |
N5—Ni1—N3 | 97.52 (19) | H1A—C1—H1B | 108.2 |
N4—Ni1—N3 | 83.24 (18) | N4—C2—C1 | 110.4 (4) |
N5—Ni1—O1 | 80.00 (16) | N4—C2—H2A | 109.6 |
N4—Ni1—O1 | 99.27 (15) | C1—C2—H2A | 109.6 |
N3—Ni1—O1 | 176.57 (17) | N4—C2—H2B | 109.6 |
N5—Ni1—N2 | 95.42 (19) | C1—C2—H2B | 109.6 |
N4—Ni1—N2 | 83.67 (17) | H2A—C2—H2B | 108.1 |
N3—Ni1—N2 | 94.0 (2) | N2—C3—C4 | 109.3 (4) |
O1—Ni1—N2 | 88.65 (16) | N2—C3—H3A | 109.8 |
N5—Ni1—N1 | 98.8 (2) | C4—C3—H3A | 109.8 |
N4—Ni1—N1 | 81.99 (18) | N2—C3—H3B | 109.8 |
N3—Ni1—N1 | 93.3 (2) | C4—C3—H3B | 109.8 |
O1—Ni1—N1 | 84.74 (17) | H3A—C3—H3B | 108.3 |
N2—Ni1—N1 | 163.02 (18) | N4—C4—C3 | 109.9 (4) |
O6—Cl1—O3 | 112.5 (8) | N4—C4—H4A | 109.7 |
O6—Cl1—O4 | 108.5 (7) | C3—C4—H4A | 109.7 |
O3—Cl1—O4 | 106.7 (7) | N4—C4—H4B | 109.7 |
O6—Cl1—O5 | 112.5 (6) | C3—C4—H4B | 109.7 |
O3—Cl1—O5 | 107.6 (5) | H4A—C4—H4B | 108.2 |
O4—Cl1—O5 | 108.8 (5) | N3—C5—C6 | 110.6 (5) |
C11—S1—C10 | 102.9 (4) | N3—C5—H5A | 109.5 |
C7—O1—Ni1 | 115.2 (3) | C6—C5—H5A | 109.5 |
H1E—O1W—H1F | 116.3 | N3—C5—H5B | 109.5 |
H2E—O2W—H2F | 115.5 | C6—C5—H5B | 109.5 |
C1—N1—Ni1 | 109.8 (3) | H5A—C5—H5B | 108.1 |
C1—N1—H1C | 109.7 | N4—C6—C5 | 113.1 (4) |
Ni1—N1—H1C | 109.7 | N4—C6—H6A | 109.0 |
C1—N1—H1D | 109.7 | C5—C6—H6A | 109.0 |
Ni1—N1—H1D | 109.7 | N4—C6—H6B | 109.0 |
H1C—N1—H1D | 108.2 | C5—C6—H6B | 109.0 |
C3—N2—Ni1 | 108.2 (3) | H6A—C6—H6B | 107.8 |
C3—N2—H2C | 110.1 | O2—C7—O1 | 125.3 (5) |
Ni1—N2—H2C | 110.1 | O2—C7—C8 | 117.1 (5) |
C3—N2—H2D | 110.1 | O1—C7—C8 | 117.7 (5) |
Ni1—N2—H2D | 110.1 | C9—C8—N5 | 115.4 (7) |
H2C—N2—H2D | 108.4 | C9—C8—C7 | 118.8 (7) |
C5—N3—Ni1 | 108.4 (3) | N5—C8—C7 | 111.0 (5) |
C5—N3—H3C | 110.0 | C9—C8—H8A | 103.1 |
Ni1—N3—H3C | 110.0 | N5—C8—H8A | 103.1 |
C5—N3—H3D | 110.0 | C7—C8—H8A | 103.1 |
Ni1—N3—H3D | 110.0 | C8—C9—C10 | 112.5 (7) |
H3C—N3—H3D | 108.4 | C8—C9—H9A | 109.1 |
C4—N4—C2 | 112.2 (4) | C10—C9—H9A | 109.1 |
C4—N4—C6 | 111.2 (4) | C8—C9—H9B | 109.1 |
C2—N4—C6 | 112.6 (4) | C10—C9—H9B | 109.1 |
C4—N4—Ni1 | 105.4 (3) | H9A—C9—H9B | 107.8 |
C2—N4—Ni1 | 105.0 (3) | C9—C10—S1 | 103.0 (6) |
C6—N4—Ni1 | 110.0 (3) | C9—C10—H10A | 111.2 |
C8—N5—Ni1 | 111.1 (4) | S1—C10—H10A | 111.2 |
C8—N5—H5C | 109.4 | C9—C10—H10B | 111.2 |
Ni1—N5—H5C | 109.4 | S1—C10—H10B | 111.2 |
C8—N5—H5D | 109.4 | H10A—C10—H10B | 109.1 |
Ni1—N5—H5D | 109.4 | S1—C11—H11A | 109.5 |
H5C—N5—H5D | 108.0 | S1—C11—H11B | 109.5 |
N1—C1—C2 | 109.6 (5) | H11A—C11—H11B | 109.5 |
N1—C1—H1A | 109.7 | S1—C11—H11C | 109.5 |
C2—C1—H1A | 109.7 | H11A—C11—H11C | 109.5 |
N1—C1—H1B | 109.7 | H11B—C11—H11C | 109.5 |
| | | |
N5—Ni1—O1—C7 | −9.3 (4) | O1—Ni1—N5—C8 | 18.5 (5) |
N4—Ni1—O1—C7 | 169.8 (4) | N2—Ni1—N5—C8 | −69.2 (5) |
N2—Ni1—O1—C7 | 86.4 (4) | N1—Ni1—N5—C8 | 101.5 (5) |
N1—Ni1—O1—C7 | −109.2 (4) | Ni1—N1—C1—C2 | 22.4 (6) |
N5—Ni1—N1—C1 | −175.4 (4) | C4—N4—C2—C1 | 164.7 (5) |
N4—Ni1—N1—C1 | 3.7 (4) | C6—N4—C2—C1 | −69.0 (6) |
N3—Ni1—N1—C1 | 86.4 (4) | Ni1—N4—C2—C1 | 50.7 (5) |
O1—Ni1—N1—C1 | −96.4 (4) | N1—C1—C2—N4 | −49.6 (6) |
N2—Ni1—N1—C1 | −28.9 (8) | Ni1—N2—C3—C4 | −30.5 (5) |
N5—Ni1—N2—C3 | −176.7 (4) | C2—N4—C4—C3 | −161.2 (4) |
N4—Ni1—N2—C3 | 4.0 (4) | C6—N4—C4—C3 | 71.7 (6) |
N3—Ni1—N2—C3 | −78.7 (4) | Ni1—N4—C4—C3 | −47.4 (5) |
O1—Ni1—N2—C3 | 103.5 (4) | N2—C3—C4—N4 | 53.5 (6) |
N1—Ni1—N2—C3 | 36.5 (8) | Ni1—N3—C5—C6 | −39.9 (6) |
N5—Ni1—N3—C5 | −157.5 (4) | C4—N4—C6—C5 | −135.9 (5) |
N4—Ni1—N3—C5 | 23.4 (4) | C2—N4—C6—C5 | 97.2 (6) |
N2—Ni1—N3—C5 | 106.5 (4) | Ni1—N4—C6—C5 | −19.6 (6) |
N1—Ni1—N3—C5 | −58.2 (4) | N3—C5—C6—N4 | 40.3 (7) |
N3—Ni1—N4—C4 | 118.1 (3) | Ni1—O1—C7—O2 | 177.2 (5) |
O1—Ni1—N4—C4 | −64.2 (3) | Ni1—O1—C7—C8 | −2.2 (7) |
N2—Ni1—N4—C4 | 23.4 (3) | Ni1—N5—C8—C9 | 114.4 (6) |
N1—Ni1—N4—C4 | −147.5 (3) | Ni1—N5—C8—C7 | −24.4 (8) |
N3—Ni1—N4—C2 | −123.3 (3) | O2—C7—C8—C9 | 61.2 (10) |
O1—Ni1—N4—C2 | 54.4 (3) | O1—C7—C8—C9 | −119.2 (8) |
N2—Ni1—N4—C2 | 142.0 (3) | O2—C7—C8—N5 | −161.5 (6) |
N1—Ni1—N4—C2 | −28.9 (3) | O1—C7—C8—N5 | 18.0 (9) |
N3—Ni1—N4—C6 | −1.8 (4) | N5—C8—C9—C10 | 69.4 (10) |
O1—Ni1—N4—C6 | 175.8 (3) | C7—C8—C9—C10 | −155.2 (6) |
N2—Ni1—N4—C6 | −96.6 (4) | C8—C9—C10—S1 | −162.5 (7) |
N1—Ni1—N4—C6 | 92.5 (4) | C11—S1—C10—C9 | −78.0 (6) |
N3—Ni1—N5—C8 | −163.9 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···S1i | 0.90 | 2.80 | 3.530 (5) | 139 |
O1W—H1E···O6ii | 0.95 | 2.03 | 2.945 (8) | 161 |
N2—H2D···O5ii | 0.90 | 2.38 | 3.263 (9) | 169 |
O1W—H1F···O2iii | 0.89 | 1.88 | 2.748 (8) | 166 |
N2—H2C···O1iv | 0.90 | 2.34 | 3.205 (5) | 163 |
N3—H3D···O4v | 0.90 | 2.54 | 3.334 (11) | 148 |
C1—H1B···O5vi | 0.97 | 2.56 | 3.431 (9) | 149 |
N1—H1D···O3 | 0.90 | 2.34 | 3.219 (11) | 165 |
O2W—H2E···N5 | 0.82 | 2.22 | 3.038 (9) | 178 |
O2W—H2F···O3 | 0.82 | 2.11 | 2.857 (12) | 152 |
N3—H3C···O3 | 0.90 | 2.60 | 3.289 (11) | 134 |
N5—H5D···O2W | 0.90 | 2.23 | 3.038 (9) | 150 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x+3/2, −y+1, z+1/2; (iii) −x+3/2, y−1/2, z; (iv) x+1/2, y, −z+3/2; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+1, −z+1. |