The title compound, [Ni(C
9H
9Br
2NO
4S)(C
8H
8N
2)(H
2O)]·C
2H
5OH, was synthesized in a water–ethanol solution. In the structure, the Ni atom is six-coordinated by three ligands to form the neutral complex, in which the Ni atom has a distorted octahedral coordination geometry. Molecules form dimers through O—H
O hydrogen bonds.
Supporting information
CCDC reference: 269811
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.009 Å
- R factor = 0.044
- wR factor = 0.093
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc.
PLAT213_ALERT_2_C Atom C3 has ADP max/min Ratio ............. 3.40 prolat
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.75 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.18 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.27 su
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O3 .. 3.09 Ang.
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
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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Aqua{2-[(
E)-(3,5-dibromo-2-oxidophenyl)methyleneamino]ethanesulfonato-
κ3O,
N,
O'}(1,10-phenanthroline-
κ2N,
N')nickel(II) ethanol solvate
top
Crystal data top
[Ni(C9H9Br2NO4S)(C8H8N2)(H2O)]·C2H6O | F(000) = 2752 |
Mr = 688.03 | Dx = 1.738 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 33 reflections |
a = 18.725 (4) Å | θ = 2.8–14.1° |
b = 19.623 (4) Å | µ = 3.90 mm−1 |
c = 15.647 (3) Å | T = 296 K |
β = 113.82 (1)° | Plate, blue |
V = 5259.6 (19) Å3 | 0.54 × 0.38 × 0.36 mm |
Z = 8 | |
Data collection top
Siemens P4 diffractometer | 2204 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 25.3°, θmin = 1.6° |
ω scans | h = 0→22 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = 0→23 |
Tmin = 0.165, Tmax = 0.246 | l = −18→17 |
5341 measured reflections | 3 standard reflections every 97 reflections |
4776 independent reflections | intensity decay: 1.1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0406P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max = 0.001 |
4776 reflections | Δρmax = 0.49 e Å−3 |
340 parameters | Δρmin = −0.62 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00032 (4) |
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 | |
Ni | 0.51779 (4) | 0.78170 (3) | 0.59556 (5) | 0.0298 (2) | |
Br1 | 0.27201 (4) | 0.71274 (4) | 0.61609 (5) | 0.0740 (3) | |
Br2 | 0.35565 (6) | 0.43891 (4) | 0.61097 (7) | 0.1218 (4) | |
S | 0.67045 (8) | 0.81258 (7) | 0.54816 (11) | 0.0363 (4) | |
O1 | 0.4361 (2) | 0.73777 (18) | 0.6297 (2) | 0.0411 (10) | |
O2 | 0.60327 (19) | 0.83451 (17) | 0.5676 (2) | 0.0378 (10) | |
O3 | 0.7432 (2) | 0.82907 (19) | 0.6256 (3) | 0.0518 (11) | |
O4 | 0.6652 (2) | 0.8363 (2) | 0.4589 (3) | 0.0545 (12) | |
O5 | 0.5732 (2) | 0.8187 (2) | 0.7304 (3) | 0.0365 (10) | |
N1 | 0.5807 (2) | 0.6924 (2) | 0.6227 (3) | 0.0350 (11) | |
N2 | 0.4596 (2) | 0.7638 (2) | 0.4508 (3) | 0.0342 (12) | |
N3 | 0.4549 (2) | 0.8732 (2) | 0.5517 (3) | 0.0338 (11) | |
C1 | 0.4212 (3) | 0.6728 (3) | 0.6256 (4) | 0.0421 (16) | |
C2 | 0.3495 (3) | 0.6478 (3) | 0.6217 (4) | 0.0490 (18) | |
C3 | 0.3316 (4) | 0.5805 (4) | 0.6183 (4) | 0.070 (2) | |
H3 | 0.2830 | 0.5673 | 0.6155 | 0.084* | |
C4 | 0.3844 (5) | 0.5314 (4) | 0.6188 (5) | 0.074 (2) | |
C5 | 0.4559 (4) | 0.5514 (3) | 0.6251 (4) | 0.0589 (19) | |
H5 | 0.4925 | 0.5187 | 0.6270 | 0.071* | |
C6 | 0.4753 (3) | 0.6209 (3) | 0.6288 (4) | 0.0418 (16) | |
C7 | 0.5525 (3) | 0.6356 (3) | 0.6328 (4) | 0.0400 (15) | |
H7 | 0.5859 | 0.5984 | 0.6443 | 0.048* | |
C8 | 0.6607 (3) | 0.6916 (3) | 0.6281 (4) | 0.0502 (17) | |
H8A | 0.6792 | 0.6449 | 0.6348 | 0.060* | |
H8B | 0.6943 | 0.7166 | 0.6832 | 0.060* | |
C9 | 0.6667 (3) | 0.7227 (3) | 0.5429 (4) | 0.0428 (15) | |
H9A | 0.6220 | 0.7087 | 0.4875 | 0.051* | |
H9B | 0.7134 | 0.7057 | 0.5374 | 0.051* | |
C10 | 0.4571 (3) | 0.7091 (3) | 0.4008 (4) | 0.0462 (16) | |
H10 | 0.4770 | 0.6685 | 0.4320 | 0.055* | |
C11 | 0.4262 (3) | 0.7091 (4) | 0.3040 (4) | 0.0583 (19) | |
H11 | 0.4260 | 0.6690 | 0.2723 | 0.070* | |
C12 | 0.3967 (4) | 0.7661 (4) | 0.2557 (5) | 0.060 (2) | |
H12 | 0.3766 | 0.7664 | 0.1908 | 0.072* | |
C13 | 0.3969 (3) | 0.8253 (3) | 0.3058 (4) | 0.0462 (17) | |
C14 | 0.3659 (4) | 0.8891 (4) | 0.2620 (5) | 0.067 (2) | |
H14 | 0.3461 | 0.8923 | 0.1972 | 0.080* | |
C15 | 0.3648 (4) | 0.9451 (4) | 0.3127 (5) | 0.068 (2) | |
H15 | 0.3457 | 0.9863 | 0.2828 | 0.081* | |
C16 | 0.3931 (3) | 0.9404 (3) | 0.4123 (4) | 0.0442 (16) | |
C17 | 0.3912 (3) | 0.9958 (3) | 0.4690 (5) | 0.058 (2) | |
H17 | 0.3709 | 1.0376 | 0.4422 | 0.070* | |
C18 | 0.4192 (3) | 0.9873 (3) | 0.5624 (5) | 0.0551 (18) | |
H18 | 0.4169 | 1.0232 | 0.5999 | 0.066* | |
C19 | 0.4513 (3) | 0.9257 (3) | 0.6032 (4) | 0.0488 (17) | |
H19 | 0.4708 | 0.9212 | 0.6678 | 0.059* | |
C20 | 0.4259 (3) | 0.8802 (3) | 0.4575 (4) | 0.0323 (14) | |
C21 | 0.4269 (3) | 0.8219 (3) | 0.4027 (4) | 0.0344 (14) | |
O6 | 0.7096 (3) | 0.8902 (3) | 0.7688 (3) | 0.0650 (13) | |
C22 | 0.7713 (4) | 0.8984 (4) | 0.8566 (5) | 0.080 (2) | |
H22A | 0.8012 | 0.8565 | 0.8736 | 0.096* | |
H22B | 0.7501 | 0.9069 | 0.9028 | 0.096* | |
C23 | 0.8234 (4) | 0.9543 (4) | 0.8587 (6) | 0.121 (3) | |
H23A | 0.8329 | 0.9534 | 0.8028 | 0.145* | |
H23B | 0.8719 | 0.9495 | 0.9121 | 0.145* | |
H23C | 0.7996 | 0.9969 | 0.8624 | 0.145* | |
H5A | 0.607 (3) | 0.848 (3) | 0.748 (5) | 0.12 (3)* | |
H5B | 0.574 (3) | 0.7883 (17) | 0.766 (3) | 0.032 (18)* | |
H6O | 0.729 (4) | 0.867 (3) | 0.740 (4) | 0.09 (3)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni | 0.0233 (4) | 0.0278 (4) | 0.0377 (4) | −0.0029 (3) | 0.0119 (3) | −0.0007 (4) |
Br1 | 0.0341 (4) | 0.1113 (7) | 0.0764 (5) | −0.0145 (4) | 0.0221 (4) | 0.0032 (5) |
Br2 | 0.1617 (10) | 0.0646 (6) | 0.1296 (8) | −0.0721 (6) | 0.0491 (7) | −0.0051 (6) |
S | 0.0293 (8) | 0.0399 (9) | 0.0426 (10) | −0.0052 (7) | 0.0176 (8) | −0.0051 (8) |
O1 | 0.032 (2) | 0.042 (3) | 0.055 (3) | −0.0122 (19) | 0.024 (2) | −0.007 (2) |
O2 | 0.038 (2) | 0.031 (2) | 0.054 (3) | −0.0071 (18) | 0.028 (2) | −0.0058 (19) |
O3 | 0.029 (2) | 0.050 (3) | 0.065 (3) | −0.009 (2) | 0.006 (2) | −0.009 (2) |
O4 | 0.058 (3) | 0.068 (3) | 0.044 (3) | 0.004 (2) | 0.027 (2) | 0.005 (2) |
O5 | 0.035 (2) | 0.037 (3) | 0.036 (3) | −0.009 (2) | 0.013 (2) | −0.002 (2) |
N1 | 0.027 (3) | 0.026 (3) | 0.052 (3) | −0.003 (2) | 0.016 (2) | −0.004 (2) |
N2 | 0.026 (3) | 0.033 (3) | 0.045 (3) | −0.009 (2) | 0.015 (2) | −0.011 (3) |
N3 | 0.021 (3) | 0.031 (3) | 0.047 (3) | −0.004 (2) | 0.012 (2) | −0.003 (3) |
C1 | 0.033 (4) | 0.057 (4) | 0.033 (4) | −0.022 (3) | 0.010 (3) | −0.007 (3) |
C2 | 0.038 (4) | 0.074 (5) | 0.036 (4) | −0.026 (4) | 0.015 (3) | −0.009 (4) |
C3 | 0.065 (5) | 0.088 (6) | 0.055 (5) | −0.063 (5) | 0.022 (4) | −0.021 (5) |
C4 | 0.099 (7) | 0.051 (5) | 0.076 (6) | −0.041 (5) | 0.040 (5) | −0.002 (4) |
C5 | 0.069 (5) | 0.045 (4) | 0.057 (5) | −0.015 (4) | 0.020 (4) | 0.007 (4) |
C6 | 0.044 (4) | 0.037 (4) | 0.047 (4) | −0.017 (3) | 0.021 (3) | −0.006 (3) |
C7 | 0.047 (4) | 0.027 (3) | 0.044 (4) | 0.004 (3) | 0.015 (3) | −0.006 (3) |
C8 | 0.032 (3) | 0.045 (4) | 0.078 (5) | 0.010 (3) | 0.026 (3) | 0.001 (4) |
C9 | 0.038 (3) | 0.035 (3) | 0.064 (4) | −0.003 (3) | 0.031 (3) | −0.015 (4) |
C10 | 0.043 (4) | 0.040 (4) | 0.054 (4) | −0.006 (3) | 0.019 (3) | 0.000 (4) |
C11 | 0.056 (4) | 0.070 (5) | 0.044 (4) | −0.011 (4) | 0.016 (4) | −0.021 (4) |
C12 | 0.047 (4) | 0.078 (6) | 0.052 (5) | −0.011 (4) | 0.015 (4) | 0.000 (4) |
C13 | 0.022 (3) | 0.058 (5) | 0.047 (5) | 0.001 (3) | 0.002 (3) | 0.012 (4) |
C14 | 0.050 (5) | 0.093 (6) | 0.042 (5) | −0.005 (5) | 0.003 (4) | 0.013 (5) |
C15 | 0.045 (4) | 0.064 (5) | 0.076 (6) | 0.020 (4) | 0.006 (4) | 0.037 (5) |
C16 | 0.039 (4) | 0.050 (4) | 0.042 (4) | 0.006 (3) | 0.014 (3) | 0.006 (4) |
C17 | 0.037 (4) | 0.044 (4) | 0.087 (6) | 0.017 (3) | 0.017 (4) | 0.025 (4) |
C18 | 0.057 (4) | 0.034 (4) | 0.074 (5) | 0.010 (3) | 0.026 (4) | −0.009 (4) |
C19 | 0.052 (4) | 0.039 (4) | 0.055 (4) | 0.004 (3) | 0.020 (4) | −0.008 (4) |
C20 | 0.013 (3) | 0.042 (4) | 0.037 (4) | 0.000 (3) | 0.004 (3) | −0.004 (3) |
C21 | 0.011 (3) | 0.049 (4) | 0.037 (4) | −0.005 (3) | 0.003 (3) | 0.008 (3) |
O6 | 0.054 (3) | 0.080 (4) | 0.056 (3) | −0.021 (3) | 0.017 (3) | −0.015 (3) |
C22 | 0.057 (5) | 0.090 (6) | 0.074 (6) | −0.016 (5) | 0.008 (5) | −0.009 (5) |
C23 | 0.079 (6) | 0.132 (8) | 0.106 (7) | −0.030 (6) | −0.009 (6) | −0.021 (6) |
Geometric parameters (Å, º) top
Ni—O1 | 2.007 (3) | C8—H8A | 0.9700 |
Ni—N1 | 2.058 (4) | C8—H8B | 0.9700 |
Ni—O5 | 2.070 (4) | C9—H9A | 0.9700 |
Ni—O2 | 2.096 (3) | C9—H9B | 0.9700 |
Ni—N3 | 2.104 (4) | C10—C11 | 1.385 (7) |
Ni—N2 | 2.109 (4) | C10—H10 | 0.9300 |
Br1—C2 | 1.907 (6) | C11—C12 | 1.339 (8) |
Br2—C4 | 1.884 (7) | C11—H11 | 0.9300 |
S—O4 | 1.438 (4) | C12—C13 | 1.401 (8) |
S—O3 | 1.447 (4) | C12—H12 | 0.9300 |
S—O2 | 1.473 (3) | C13—C21 | 1.388 (7) |
S—C9 | 1.765 (5) | C13—C14 | 1.433 (8) |
O1—C1 | 1.301 (6) | C14—C15 | 1.361 (8) |
O5—H5A | 0.82 (7) | C14—H14 | 0.9300 |
O5—H5B | 0.81 (4) | C15—C16 | 1.431 (8) |
N1—C7 | 1.271 (6) | C15—H15 | 0.9300 |
N1—C8 | 1.465 (6) | C16—C20 | 1.386 (7) |
N2—C10 | 1.319 (6) | C16—C17 | 1.412 (8) |
N2—C21 | 1.366 (6) | C17—C18 | 1.349 (8) |
N3—C19 | 1.327 (6) | C17—H17 | 0.9300 |
N3—C20 | 1.356 (6) | C18—C19 | 1.385 (8) |
C1—C2 | 1.407 (7) | C18—H18 | 0.9300 |
C1—C6 | 1.424 (8) | C19—H19 | 0.9300 |
C2—C3 | 1.358 (8) | C20—C21 | 1.435 (7) |
C3—C4 | 1.377 (9) | O6—C22 | 1.403 (7) |
C3—H3 | 0.9300 | O6—H6O | 0.82 (7) |
C4—C5 | 1.361 (9) | C22—C23 | 1.459 (9) |
C5—C6 | 1.405 (7) | C22—H22A | 0.9700 |
C5—H5 | 0.9300 | C22—H22B | 0.9700 |
C6—C7 | 1.452 (7) | C23—H23A | 0.9600 |
C7—H7 | 0.9300 | C23—H23B | 0.9600 |
C8—C9 | 1.512 (7) | C23—H23C | 0.9600 |
| | | |
O1—Ni—N1 | 90.79 (16) | N1—C8—H8B | 109.1 |
O1—Ni—O5 | 90.08 (16) | C9—C8—H8B | 109.1 |
N1—Ni—O5 | 94.54 (17) | H8A—C8—H8B | 107.8 |
O1—Ni—O2 | 175.06 (14) | C8—C9—S | 112.2 (4) |
N1—Ni—O2 | 92.40 (15) | C8—C9—H9A | 109.2 |
O5—Ni—O2 | 85.90 (16) | S—C9—H9A | 109.2 |
O1—Ni—N3 | 93.85 (15) | C8—C9—H9B | 109.2 |
N1—Ni—N3 | 172.77 (18) | S—C9—H9B | 109.2 |
O5—Ni—N3 | 90.99 (18) | H9A—C9—H9B | 107.9 |
O2—Ni—N3 | 83.35 (14) | N2—C10—C11 | 123.2 (6) |
O1—Ni—N2 | 95.51 (15) | N2—C10—H10 | 118.4 |
N1—Ni—N2 | 94.85 (17) | C11—C10—H10 | 118.4 |
O5—Ni—N2 | 168.99 (17) | C12—C11—C10 | 120.8 (7) |
O2—Ni—N2 | 87.98 (14) | C12—C11—H11 | 119.6 |
N3—Ni—N2 | 79.20 (18) | C10—C11—H11 | 119.6 |
O4—S—O3 | 114.4 (2) | C11—C12—C13 | 118.0 (6) |
O4—S—O2 | 112.2 (2) | C11—C12—H12 | 121.0 |
O3—S—O2 | 110.8 (2) | C13—C12—H12 | 121.0 |
O4—S—C9 | 107.0 (3) | C21—C13—C12 | 118.7 (6) |
O3—S—C9 | 105.6 (2) | C21—C13—C14 | 118.2 (6) |
O2—S—C9 | 106.3 (2) | C12—C13—C14 | 123.1 (6) |
C1—O1—Ni | 125.4 (4) | C15—C14—C13 | 121.6 (6) |
S—O2—Ni | 133.4 (2) | C15—C14—H14 | 119.2 |
Ni—O5—H5A | 126 (5) | C13—C14—H14 | 119.2 |
Ni—O5—H5B | 108 (3) | C14—C15—C16 | 119.8 (6) |
H5A—O5—H5B | 119 (6) | C14—C15—H15 | 120.1 |
C7—N1—C8 | 116.7 (5) | C16—C15—H15 | 120.1 |
C7—N1—Ni | 122.7 (4) | C20—C16—C17 | 117.0 (6) |
C8—N1—Ni | 120.5 (3) | C20—C16—C15 | 120.2 (6) |
C10—N2—C21 | 116.8 (5) | C17—C16—C15 | 122.8 (6) |
C10—N2—Ni | 130.7 (4) | C18—C17—C16 | 119.2 (6) |
C21—N2—Ni | 112.1 (4) | C18—C17—H17 | 120.4 |
C19—N3—C20 | 119.0 (5) | C16—C17—H17 | 120.4 |
C19—N3—Ni | 128.6 (4) | C17—C18—C19 | 120.9 (6) |
C20—N3—Ni | 111.6 (4) | C17—C18—H18 | 119.5 |
O1—C1—C2 | 121.8 (6) | C19—C18—H18 | 119.5 |
O1—C1—C6 | 124.3 (5) | N3—C19—C18 | 121.1 (6) |
C2—C1—C6 | 113.8 (6) | N3—C19—H19 | 119.4 |
C3—C2—C1 | 123.9 (7) | C18—C19—H19 | 119.4 |
C3—C2—Br1 | 118.5 (5) | N3—C20—C16 | 122.8 (5) |
C1—C2—Br1 | 117.6 (5) | N3—C20—C21 | 118.2 (5) |
C2—C3—C4 | 120.9 (6) | C16—C20—C21 | 119.0 (5) |
C2—C3—H3 | 119.5 | N2—C21—C13 | 122.4 (6) |
C4—C3—H3 | 119.5 | N2—C21—C20 | 116.5 (5) |
C5—C4—C3 | 118.9 (6) | C13—C21—C20 | 121.1 (6) |
C5—C4—Br2 | 122.0 (7) | C22—O6—H6O | 104 (5) |
C3—C4—Br2 | 119.2 (6) | O6—C22—C23 | 112.8 (6) |
C4—C5—C6 | 120.8 (7) | O6—C22—H22A | 109.0 |
C4—C5—H5 | 119.6 | C23—C22—H22A | 109.0 |
C6—C5—H5 | 119.6 | O6—C22—H22B | 109.0 |
C5—C6—C1 | 121.7 (6) | C23—C22—H22B | 109.0 |
C5—C6—C7 | 115.5 (6) | H22A—C22—H22B | 107.8 |
C1—C6—C7 | 122.8 (5) | C22—C23—H23A | 109.5 |
N1—C7—C6 | 128.7 (5) | C22—C23—H23B | 109.5 |
N1—C7—H7 | 115.6 | H23A—C23—H23B | 109.5 |
C6—C7—H7 | 115.6 | C22—C23—H23C | 109.5 |
N1—C8—C9 | 112.5 (5) | H23A—C23—H23C | 109.5 |
N1—C8—H8A | 109.1 | H23B—C23—H23C | 109.5 |
C9—C8—H8A | 109.1 | | |
| | | |
N1—Ni—O1—C1 | −25.1 (4) | O1—C1—C6—C5 | 179.3 (6) |
O5—Ni—O1—C1 | −119.6 (4) | C2—C1—C6—C5 | 1.9 (8) |
N3—Ni—O1—C1 | 149.4 (4) | O1—C1—C6—C7 | −2.8 (9) |
N2—Ni—O1—C1 | 69.9 (4) | C2—C1—C6—C7 | 179.8 (5) |
O4—S—O2—Ni | 120.9 (3) | C8—N1—C7—C6 | −178.5 (5) |
O3—S—O2—Ni | −109.9 (3) | Ni—N1—C7—C6 | −0.6 (8) |
C9—S—O2—Ni | 4.3 (4) | C5—C6—C7—N1 | 168.5 (6) |
N1—Ni—O2—S | 15.3 (3) | C1—C6—C7—N1 | −9.5 (10) |
O5—Ni—O2—S | 109.7 (3) | C7—N1—C8—C9 | 125.1 (5) |
N3—Ni—O2—S | −158.9 (3) | Ni—N1—C8—C9 | −52.9 (6) |
N2—Ni—O2—S | −79.5 (3) | N1—C8—C9—S | 81.1 (5) |
O1—Ni—N1—C7 | 13.7 (5) | O4—S—C9—C8 | −172.2 (4) |
O5—Ni—N1—C7 | 103.9 (5) | O3—S—C9—C8 | 65.5 (4) |
O2—Ni—N1—C7 | −170.0 (4) | O2—S—C9—C8 | −52.2 (4) |
N2—Ni—N1—C7 | −81.9 (5) | C21—N2—C10—C11 | 2.7 (8) |
O1—Ni—N1—C8 | −168.4 (4) | Ni—N2—C10—C11 | −169.2 (4) |
O5—Ni—N1—C8 | −78.2 (4) | N2—C10—C11—C12 | −0.1 (9) |
O2—Ni—N1—C8 | 7.8 (4) | C10—C11—C12—C13 | −0.9 (10) |
N2—Ni—N1—C8 | 96.0 (4) | C11—C12—C13—C21 | −0.6 (9) |
O1—Ni—N2—C10 | −82.2 (5) | C11—C12—C13—C14 | −179.1 (6) |
N1—Ni—N2—C10 | 9.1 (5) | C21—C13—C14—C15 | −0.6 (9) |
O5—Ni—N2—C10 | 157.6 (7) | C12—C13—C14—C15 | 177.9 (6) |
O2—Ni—N2—C10 | 101.3 (5) | C13—C14—C15—C16 | −1.8 (10) |
N3—Ni—N2—C10 | −175.0 (5) | C14—C15—C16—C20 | 4.0 (9) |
O1—Ni—N2—C21 | 105.6 (3) | C14—C15—C16—C17 | −177.8 (6) |
N1—Ni—N2—C21 | −163.1 (3) | C20—C16—C17—C18 | −1.5 (9) |
O5—Ni—N2—C21 | −14.6 (10) | C15—C16—C17—C18 | −179.8 (6) |
O2—Ni—N2—C21 | −70.9 (3) | C16—C17—C18—C19 | 1.6 (9) |
N3—Ni—N2—C21 | 12.8 (3) | C20—N3—C19—C18 | −0.4 (8) |
O1—Ni—N3—C19 | 82.6 (5) | Ni—N3—C19—C18 | 167.6 (4) |
O5—Ni—N3—C19 | −7.5 (5) | C17—C18—C19—N3 | −0.6 (9) |
O2—Ni—N3—C19 | −93.3 (5) | C19—N3—C20—C16 | 0.4 (8) |
N2—Ni—N3—C19 | 177.5 (5) | Ni—N3—C20—C16 | −169.6 (4) |
O1—Ni—N3—C20 | −108.6 (3) | C19—N3—C20—C21 | −177.1 (5) |
O5—Ni—N3—C20 | 161.3 (3) | Ni—N3—C20—C21 | 13.0 (5) |
O2—Ni—N3—C20 | 75.5 (3) | C17—C16—C20—N3 | 0.5 (8) |
N2—Ni—N3—C20 | −13.7 (3) | C15—C16—C20—N3 | 178.8 (5) |
Ni—O1—C1—C2 | −159.5 (4) | C17—C16—C20—C21 | 178.0 (5) |
Ni—O1—C1—C6 | 23.3 (8) | C15—C16—C20—C21 | −3.7 (8) |
O1—C1—C2—C3 | −179.3 (6) | C10—N2—C21—C13 | −4.3 (7) |
C6—C1—C2—C3 | −1.9 (9) | Ni—N2—C21—C13 | 169.1 (4) |
O1—C1—C2—Br1 | 3.1 (7) | C10—N2—C21—C20 | 176.7 (4) |
C6—C1—C2—Br1 | −179.4 (4) | Ni—N2—C21—C20 | −10.0 (5) |
C1—C2—C3—C4 | 0.2 (11) | C12—C13—C21—N2 | 3.3 (8) |
Br1—C2—C3—C4 | 177.7 (5) | C14—C13—C21—N2 | −178.1 (5) |
C2—C3—C4—C5 | 1.6 (11) | C12—C13—C21—C20 | −177.7 (5) |
C2—C3—C4—Br2 | −178.5 (5) | C14—C13—C21—C20 | 0.9 (8) |
C3—C4—C5—C6 | −1.5 (11) | N3—C20—C21—N2 | −2.1 (7) |
Br2—C4—C5—C6 | 178.6 (5) | C16—C20—C21—N2 | −179.6 (5) |
C4—C5—C6—C1 | −0.3 (10) | N3—C20—C21—C13 | 178.9 (5) |
C4—C5—C6—C7 | −178.3 (6) | C16—C20—C21—C13 | 1.3 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O6 | 0.82 (7) | 1.99 (6) | 2.759 (7) | 156 (6) |
O5—H5B···O1i | 0.81 (4) | 1.98 (4) | 2.767 (5) | 162 (5) |
O6—H6O···O3 | 0.82 (7) | 2.05 (6) | 2.828 (7) | 157 (6) |
Symmetry code: (i) −x+1, y, −z+3/2. |