The title mononuclear nickel(II) complex, [Ni(C
13H
18BrN
2O)N
3], contains two molecules in the asymmetric unit. Each Ni
II atom is four-coordinated by one phenolate O atom, one imine N atom and one amine N atom from a Schiff base ligand, and by one terminal N atom of an azide anion, forming a square-planar coordination. In the crystal structure, adjacent molecules are linked through C—H
N interactions, forming chains along the
a axis.
Supporting information
CCDC reference: 605024
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.056
- wR factor = 0.154
- Data-to-parameter ratio = 18.1
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96
PLAT220_ALERT_2_C Large Non-Solvent N Ueq(max)/Ueq(min) ... 3.12 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N9
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C13 H18 Br1 N5 Ni1 O1
Atom count from _chemical_formula_moiety:
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
1 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.
Azido{4-bromo-2-[(2-diethylaminoethylimino)methyl]phenolato}nickel(II)
top
Crystal data top
[Ni(C13H18BrN2O)N3] | Z = 4 |
Mr = 398.94 | F(000) = 808 |
Triclinic, P1 | Dx = 1.697 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.261 (1) Å | Cell parameters from 3098 reflections |
b = 10.178 (1) Å | θ = 2.3–25.4° |
c = 17.274 (2) Å | µ = 3.81 mm−1 |
α = 100.90 (1)° | T = 298 K |
β = 100.88 (1)° | Block, green |
γ = 93.66 (1)° | 0.18 × 0.14 × 0.13 mm |
V = 1561.7 (3) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 6917 independent reflections |
Radiation source: fine-focus sealed tube | 4684 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scan | θmax = 27.5°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→11 |
Tmin = 0.547, Tmax = 0.638 | k = −13→13 |
13422 measured reflections | l = −22→22 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.086P)2] where P = (Fo2 + 2Fc2)/3 |
6917 reflections | (Δ/σ)max = 0.001 |
383 parameters | Δρmax = 1.10 e Å−3 |
0 restraints | Δρmin = −0.78 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 | 0.33084 (7) | 0.45740 (6) | 0.22086 (3) | 0.03942 (17) | |
Ni2 | 0.35132 (6) | −0.03017 (5) | 0.22228 (3) | 0.03759 (17) | |
Br1 | 0.23201 (7) | 1.05122 (6) | 0.50309 (4) | 0.0702 (2) | |
Br2 | 0.77190 (6) | 0.57782 (6) | 0.47511 (3) | 0.05949 (19) | |
O1 | 0.2223 (4) | 0.5040 (3) | 0.2979 (2) | 0.0486 (8) | |
O2 | 0.5400 (3) | 0.0297 (3) | 0.2769 (2) | 0.0482 (8) | |
N1 | 0.4866 (4) | 0.5864 (4) | 0.2714 (2) | 0.0391 (9) | |
N2 | 0.4465 (4) | 0.4028 (4) | 0.1382 (2) | 0.0406 (9) | |
N3 | 0.2666 (4) | 0.0969 (4) | 0.2862 (2) | 0.0396 (9) | |
N4 | 0.1505 (4) | −0.1007 (4) | 0.1645 (2) | 0.0384 (8) | |
N5 | 0.1736 (6) | 0.3244 (4) | 0.1645 (3) | 0.0582 (12) | |
N6 | 0.0523 (6) | 0.3352 (5) | 0.1749 (3) | 0.0669 (14) | |
N7 | −0.0668 (7) | 0.3386 (7) | 0.1833 (5) | 0.122 (3) | |
N8 | 0.4290 (5) | −0.1646 (4) | 0.1544 (3) | 0.0493 (10) | |
N9 | 0.5515 (5) | −0.1502 (4) | 0.1449 (3) | 0.0502 (11) | |
N10 | 0.6683 (6) | −0.1418 (6) | 0.1327 (4) | 0.0886 (18) | |
C1 | 0.3572 (5) | 0.7192 (5) | 0.3600 (3) | 0.0407 (10) | |
C2 | 0.2341 (5) | 0.6233 (5) | 0.3466 (3) | 0.0421 (11) | |
C3 | 0.1172 (6) | 0.6560 (5) | 0.3833 (3) | 0.0516 (13) | |
H3 | 0.0370 | 0.5920 | 0.3760 | 0.062* | |
C4 | 0.1167 (6) | 0.7799 (5) | 0.4300 (3) | 0.0542 (13) | |
H4 | 0.0367 | 0.8000 | 0.4539 | 0.065* | |
C5 | 0.2371 (6) | 0.8762 (5) | 0.4418 (3) | 0.0508 (12) | |
C6 | 0.3552 (6) | 0.8464 (5) | 0.4087 (3) | 0.0488 (12) | |
H6 | 0.4359 | 0.9107 | 0.4181 | 0.059* | |
C7 | 0.4819 (5) | 0.6923 (5) | 0.3248 (3) | 0.0424 (11) | |
H7 | 0.5649 | 0.7549 | 0.3412 | 0.051* | |
C8 | 0.6216 (6) | 0.5644 (5) | 0.2404 (3) | 0.0505 (12) | |
H8A | 0.6769 | 0.5018 | 0.2670 | 0.061* | |
H8B | 0.6838 | 0.6485 | 0.2499 | 0.061* | |
C9 | 0.5736 (6) | 0.5074 (5) | 0.1515 (3) | 0.0473 (12) | |
H9A | 0.5446 | 0.5785 | 0.1233 | 0.057* | |
H9B | 0.6548 | 0.4680 | 0.1308 | 0.057* | |
C10 | 0.5000 (7) | 0.2710 (5) | 0.1515 (3) | 0.0537 (13) | |
H10A | 0.4157 | 0.2115 | 0.1541 | 0.064* | |
H10B | 0.5670 | 0.2869 | 0.2035 | 0.064* | |
C11 | 0.5778 (7) | 0.1990 (6) | 0.0890 (4) | 0.0664 (16) | |
H11A | 0.5112 | 0.1774 | 0.0375 | 0.100* | |
H11B | 0.6096 | 0.1176 | 0.1040 | 0.100* | |
H11C | 0.6622 | 0.2561 | 0.0858 | 0.100* | |
C12 | 0.3592 (6) | 0.3863 (5) | 0.0534 (3) | 0.0521 (13) | |
H12A | 0.4268 | 0.3784 | 0.0166 | 0.063* | |
H12B | 0.2935 | 0.3036 | 0.0402 | 0.063* | |
C13 | 0.2692 (6) | 0.5013 (6) | 0.0414 (3) | 0.0598 (14) | |
H13A | 0.1893 | 0.4989 | 0.0695 | 0.090* | |
H13B | 0.2301 | 0.4937 | −0.0150 | 0.090* | |
H13C | 0.3308 | 0.5848 | 0.0621 | 0.090* | |
C14 | 0.4892 (5) | 0.2383 (5) | 0.3527 (3) | 0.0390 (10) | |
C15 | 0.5849 (5) | 0.1479 (5) | 0.3233 (3) | 0.0394 (10) | |
C16 | 0.7368 (5) | 0.1898 (5) | 0.3433 (3) | 0.0495 (12) | |
H16 | 0.8021 | 0.1315 | 0.3249 | 0.059* | |
C17 | 0.7916 (5) | 0.3132 (5) | 0.3887 (3) | 0.0487 (12) | |
H17 | 0.8930 | 0.3384 | 0.4013 | 0.058* | |
C18 | 0.6959 (5) | 0.4013 (5) | 0.4161 (3) | 0.0441 (11) | |
C19 | 0.5471 (5) | 0.3653 (5) | 0.3999 (3) | 0.0425 (11) | |
H19 | 0.4844 | 0.4247 | 0.4200 | 0.051* | |
C20 | 0.3330 (5) | 0.2038 (5) | 0.3345 (3) | 0.0406 (10) | |
H20 | 0.2755 | 0.2632 | 0.3596 | 0.049* | |
C21 | 0.1058 (5) | 0.0710 (5) | 0.2737 (3) | 0.0474 (12) | |
H21A | 0.0621 | 0.1548 | 0.2851 | 0.057* | |
H21B | 0.0796 | 0.0141 | 0.3092 | 0.057* | |
C22 | 0.0506 (5) | 0.0021 (5) | 0.1875 (3) | 0.0466 (12) | |
H22A | −0.0490 | −0.0407 | 0.1804 | 0.056* | |
H22B | 0.0481 | 0.0675 | 0.1532 | 0.056* | |
C23 | 0.1216 (6) | −0.2251 (5) | 0.1975 (3) | 0.0538 (14) | |
H23A | 0.1265 | −0.1976 | 0.2549 | 0.065* | |
H23B | 0.2005 | −0.2816 | 0.1904 | 0.065* | |
C24 | −0.0247 (7) | −0.3088 (6) | 0.1600 (5) | 0.092 (3) | |
H24A | −0.1042 | −0.2546 | 0.1670 | 0.138* | |
H24B | −0.0334 | −0.3840 | 0.1856 | 0.138* | |
H24C | −0.0292 | −0.3409 | 0.1035 | 0.138* | |
C25 | 0.1300 (6) | −0.1347 (5) | 0.0754 (3) | 0.0526 (13) | |
H25A | 0.0251 | −0.1535 | 0.0524 | 0.063* | |
H25B | 0.1757 | −0.2164 | 0.0605 | 0.063* | |
C26 | 0.1927 (7) | −0.0281 (6) | 0.0388 (3) | 0.0612 (15) | |
H26A | 0.1504 | 0.0541 | 0.0543 | 0.092* | |
H26B | 0.1700 | −0.0560 | −0.0188 | 0.092* | |
H26C | 0.2980 | −0.0139 | 0.0575 | 0.092* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0463 (4) | 0.0283 (3) | 0.0450 (3) | 0.0031 (3) | 0.0153 (3) | 0.0049 (2) |
Ni2 | 0.0331 (3) | 0.0276 (3) | 0.0486 (3) | 0.0022 (2) | 0.0041 (2) | 0.0037 (2) |
Br1 | 0.0684 (4) | 0.0537 (4) | 0.0772 (4) | 0.0124 (3) | 0.0164 (3) | −0.0180 (3) |
Br2 | 0.0615 (4) | 0.0452 (3) | 0.0620 (3) | −0.0122 (3) | 0.0131 (3) | −0.0080 (2) |
O1 | 0.056 (2) | 0.0343 (18) | 0.059 (2) | 0.0021 (15) | 0.0270 (17) | 0.0041 (16) |
O2 | 0.0360 (18) | 0.0382 (19) | 0.061 (2) | 0.0052 (15) | 0.0033 (15) | −0.0059 (16) |
N1 | 0.040 (2) | 0.039 (2) | 0.039 (2) | 0.0044 (17) | 0.0123 (17) | 0.0057 (17) |
N2 | 0.053 (2) | 0.027 (2) | 0.044 (2) | 0.0064 (17) | 0.0166 (18) | 0.0061 (16) |
N3 | 0.036 (2) | 0.034 (2) | 0.047 (2) | 0.0007 (16) | 0.0091 (17) | 0.0042 (17) |
N4 | 0.036 (2) | 0.0224 (18) | 0.052 (2) | 0.0015 (15) | −0.0001 (17) | 0.0059 (16) |
N5 | 0.062 (3) | 0.036 (2) | 0.075 (3) | −0.009 (2) | 0.025 (2) | 0.000 (2) |
N6 | 0.058 (3) | 0.032 (3) | 0.106 (4) | −0.004 (2) | 0.015 (3) | 0.006 (3) |
N7 | 0.065 (4) | 0.069 (4) | 0.218 (9) | −0.008 (3) | 0.026 (5) | 0.005 (5) |
N8 | 0.044 (3) | 0.029 (2) | 0.069 (3) | 0.0050 (18) | 0.008 (2) | −0.0037 (19) |
N9 | 0.044 (3) | 0.029 (2) | 0.069 (3) | 0.0068 (18) | 0.004 (2) | −0.0055 (19) |
N10 | 0.054 (4) | 0.068 (4) | 0.139 (5) | 0.012 (3) | 0.030 (3) | −0.003 (4) |
C1 | 0.037 (3) | 0.040 (3) | 0.043 (2) | 0.007 (2) | 0.008 (2) | 0.003 (2) |
C2 | 0.048 (3) | 0.035 (3) | 0.045 (3) | 0.005 (2) | 0.013 (2) | 0.008 (2) |
C3 | 0.054 (3) | 0.048 (3) | 0.058 (3) | 0.005 (2) | 0.027 (3) | 0.008 (2) |
C4 | 0.060 (3) | 0.049 (3) | 0.058 (3) | 0.014 (3) | 0.030 (3) | 0.002 (3) |
C5 | 0.055 (3) | 0.048 (3) | 0.046 (3) | 0.008 (2) | 0.013 (2) | −0.004 (2) |
C6 | 0.046 (3) | 0.046 (3) | 0.050 (3) | 0.003 (2) | 0.008 (2) | 0.001 (2) |
C7 | 0.037 (3) | 0.046 (3) | 0.040 (2) | 0.000 (2) | 0.003 (2) | 0.005 (2) |
C8 | 0.045 (3) | 0.052 (3) | 0.054 (3) | 0.001 (2) | 0.019 (2) | 0.005 (2) |
C9 | 0.055 (3) | 0.039 (3) | 0.051 (3) | 0.003 (2) | 0.020 (2) | 0.006 (2) |
C10 | 0.076 (4) | 0.031 (3) | 0.063 (3) | 0.019 (3) | 0.027 (3) | 0.015 (2) |
C11 | 0.075 (4) | 0.043 (3) | 0.092 (4) | 0.021 (3) | 0.037 (3) | 0.015 (3) |
C12 | 0.072 (4) | 0.039 (3) | 0.045 (3) | 0.004 (3) | 0.017 (3) | 0.002 (2) |
C13 | 0.071 (4) | 0.049 (3) | 0.059 (3) | 0.013 (3) | 0.007 (3) | 0.014 (3) |
C14 | 0.033 (2) | 0.042 (3) | 0.042 (2) | 0.001 (2) | 0.0098 (19) | 0.006 (2) |
C15 | 0.039 (3) | 0.037 (3) | 0.041 (2) | 0.002 (2) | 0.007 (2) | 0.006 (2) |
C16 | 0.036 (3) | 0.048 (3) | 0.058 (3) | 0.006 (2) | 0.007 (2) | −0.002 (2) |
C17 | 0.035 (3) | 0.049 (3) | 0.055 (3) | −0.002 (2) | 0.003 (2) | 0.004 (2) |
C18 | 0.047 (3) | 0.041 (3) | 0.040 (2) | −0.002 (2) | 0.009 (2) | 0.001 (2) |
C19 | 0.044 (3) | 0.040 (3) | 0.042 (2) | 0.002 (2) | 0.013 (2) | 0.004 (2) |
C20 | 0.044 (3) | 0.034 (2) | 0.045 (3) | 0.003 (2) | 0.014 (2) | 0.004 (2) |
C21 | 0.032 (3) | 0.045 (3) | 0.065 (3) | 0.004 (2) | 0.014 (2) | 0.007 (2) |
C22 | 0.033 (3) | 0.038 (3) | 0.067 (3) | 0.003 (2) | 0.005 (2) | 0.011 (2) |
C23 | 0.042 (3) | 0.037 (3) | 0.081 (4) | 0.004 (2) | −0.001 (3) | 0.025 (3) |
C24 | 0.054 (4) | 0.051 (4) | 0.169 (7) | −0.012 (3) | −0.002 (4) | 0.047 (4) |
C25 | 0.054 (3) | 0.037 (3) | 0.058 (3) | 0.009 (2) | −0.003 (2) | 0.000 (2) |
C26 | 0.075 (4) | 0.052 (3) | 0.056 (3) | 0.017 (3) | 0.012 (3) | 0.009 (3) |
Geometric parameters (Å, º) top
Ni1—O1 | 1.826 (3) | C9—H9B | 0.97 |
Ni1—N1 | 1.848 (4) | C10—C11 | 1.511 (7) |
Ni1—N5 | 1.901 (5) | C10—H10A | 0.97 |
Ni1—N2 | 1.962 (4) | C10—H10B | 0.97 |
Ni2—O2 | 1.827 (3) | C11—H11A | 0.96 |
Ni2—N3 | 1.850 (4) | C11—H11B | 0.96 |
Ni2—N8 | 1.898 (4) | C11—H11C | 0.96 |
Ni2—N4 | 1.957 (4) | C12—C13 | 1.502 (7) |
Br1—C5 | 1.901 (5) | C12—H12A | 0.97 |
Br2—C18 | 1.908 (5) | C12—H12B | 0.97 |
O1—C2 | 1.324 (6) | C13—H13A | 0.96 |
O2—C15 | 1.307 (5) | C13—H13B | 0.96 |
N1—C7 | 1.288 (6) | C13—H13C | 0.96 |
N1—C8 | 1.463 (6) | C14—C19 | 1.405 (6) |
N2—C9 | 1.489 (6) | C14—C15 | 1.410 (6) |
N2—C10 | 1.503 (6) | C14—C20 | 1.427 (6) |
N2—C12 | 1.506 (6) | C15—C16 | 1.402 (6) |
N3—C20 | 1.280 (6) | C16—C17 | 1.359 (7) |
N3—C21 | 1.463 (6) | C16—H16 | 0.93 |
N4—C25 | 1.486 (6) | C17—C18 | 1.383 (7) |
N4—C22 | 1.487 (6) | C17—H17 | 0.93 |
N4—C23 | 1.512 (6) | C18—C19 | 1.364 (6) |
N5—N6 | 1.178 (7) | C19—H19 | 0.93 |
N6—N7 | 1.142 (8) | C20—H20 | 0.93 |
N8—N9 | 1.181 (6) | C21—C22 | 1.498 (7) |
N9—N10 | 1.141 (6) | C21—H21A | 0.97 |
C1—C2 | 1.406 (7) | C21—H21B | 0.97 |
C1—C6 | 1.408 (7) | C22—H22A | 0.97 |
C1—C7 | 1.422 (6) | C22—H22B | 0.97 |
C2—C3 | 1.382 (7) | C23—C24 | 1.515 (7) |
C3—C4 | 1.363 (7) | C23—H23A | 0.97 |
C3—H3 | 0.93 | C23—H23B | 0.97 |
C4—C5 | 1.394 (7) | C24—H24A | 0.96 |
C4—H4 | 0.93 | C24—H24B | 0.96 |
C5—C6 | 1.352 (7) | C24—H24C | 0.96 |
C6—H6 | 0.93 | C25—C26 | 1.493 (8) |
C7—H7 | 0.93 | C25—H25A | 0.97 |
C8—C9 | 1.506 (7) | C25—H25B | 0.97 |
C8—H8A | 0.97 | C26—H26A | 0.96 |
C8—H8B | 0.97 | C26—H26B | 0.96 |
C9—H9A | 0.97 | C26—H26C | 0.96 |
| | | |
O1—Ni1—N1 | 93.92 (16) | C10—C11—H11A | 109.5 |
O1—Ni1—N5 | 88.47 (18) | C10—C11—H11B | 109.5 |
N1—Ni1—N5 | 177.44 (18) | H11A—C11—H11B | 109.5 |
O1—Ni1—N2 | 178.64 (14) | C10—C11—H11C | 109.5 |
N1—Ni1—N2 | 87.01 (17) | H11A—C11—H11C | 109.5 |
N5—Ni1—N2 | 90.62 (19) | H11B—C11—H11C | 109.5 |
O2—Ni2—N3 | 94.06 (16) | C13—C12—N2 | 113.1 (4) |
O2—Ni2—N8 | 88.68 (16) | C13—C12—H12A | 109.0 |
N3—Ni2—N8 | 177.23 (17) | N2—C12—H12A | 109.0 |
O2—Ni2—N4 | 177.95 (15) | C13—C12—H12B | 109.0 |
N3—Ni2—N4 | 87.13 (16) | N2—C12—H12B | 109.0 |
N8—Ni2—N4 | 90.13 (17) | H12A—C12—H12B | 107.8 |
C2—O1—Ni1 | 125.7 (3) | C12—C13—H13A | 109.5 |
C15—O2—Ni2 | 126.5 (3) | C12—C13—H13B | 109.5 |
C7—N1—C8 | 120.2 (4) | H13A—C13—H13B | 109.5 |
C7—N1—Ni1 | 126.3 (3) | C12—C13—H13C | 109.5 |
C8—N1—Ni1 | 113.3 (3) | H13A—C13—H13C | 109.5 |
C9—N2—C10 | 110.5 (4) | H13B—C13—H13C | 109.5 |
C9—N2—C12 | 109.2 (4) | C19—C14—C15 | 120.0 (4) |
C10—N2—C12 | 109.9 (4) | C19—C14—C20 | 118.9 (4) |
C9—N2—Ni1 | 107.8 (3) | C15—C14—C20 | 121.1 (4) |
C10—N2—Ni1 | 105.9 (3) | O2—C15—C16 | 118.4 (4) |
C12—N2—Ni1 | 113.5 (3) | O2—C15—C14 | 123.9 (4) |
C20—N3—C21 | 119.6 (4) | C16—C15—C14 | 117.6 (4) |
C20—N3—Ni2 | 126.7 (3) | C17—C16—C15 | 121.9 (5) |
C21—N3—Ni2 | 113.7 (3) | C17—C16—H16 | 119.0 |
C25—N4—C22 | 109.3 (3) | C15—C16—H16 | 119.0 |
C25—N4—C23 | 110.8 (4) | C16—C17—C18 | 119.6 (5) |
C22—N4—C23 | 111.0 (4) | C16—C17—H17 | 120.2 |
C25—N4—Ni2 | 115.2 (3) | C18—C17—H17 | 120.2 |
C22—N4—Ni2 | 107.4 (3) | C19—C18—C17 | 121.2 (5) |
C23—N4—Ni2 | 102.9 (3) | C19—C18—Br2 | 119.2 (4) |
N6—N5—Ni1 | 120.5 (4) | C17—C18—Br2 | 119.6 (4) |
N7—N6—N5 | 176.5 (6) | C18—C19—C14 | 119.7 (4) |
N9—N8—Ni2 | 121.3 (3) | C18—C19—H19 | 120.2 |
N10—N9—N8 | 176.6 (6) | C14—C19—H19 | 120.2 |
C2—C1—C6 | 118.8 (4) | N3—C20—C14 | 124.6 (4) |
C2—C1—C7 | 122.0 (4) | N3—C20—H20 | 117.7 |
C6—C1—C7 | 119.2 (4) | C14—C20—H20 | 117.7 |
O1—C2—C3 | 118.0 (5) | N3—C21—C22 | 107.2 (4) |
O1—C2—C1 | 123.1 (4) | N3—C21—H21A | 110.3 |
C3—C2—C1 | 118.9 (5) | C22—C21—H21A | 110.3 |
C4—C3—C2 | 121.6 (5) | N3—C21—H21B | 110.3 |
C4—C3—H3 | 119.2 | C22—C21—H21B | 110.3 |
C2—C3—H3 | 119.2 | H21A—C21—H21B | 108.5 |
C3—C4—C5 | 119.6 (5) | N4—C22—C21 | 109.2 (4) |
C3—C4—H4 | 120.2 | N4—C22—H22A | 109.8 |
C5—C4—H4 | 120.2 | C21—C22—H22A | 109.8 |
C6—C5—C4 | 120.5 (5) | N4—C22—H22B | 109.8 |
C6—C5—Br1 | 120.2 (4) | C21—C22—H22B | 109.8 |
C4—C5—Br1 | 119.3 (4) | H22A—C22—H22B | 108.3 |
C5—C6—C1 | 120.7 (5) | N4—C23—C24 | 115.8 (4) |
C5—C6—H6 | 119.7 | N4—C23—H23A | 108.3 |
C1—C6—H6 | 119.7 | C24—C23—H23A | 108.3 |
N1—C7—C1 | 123.9 (5) | N4—C23—H23B | 108.3 |
N1—C7—H7 | 118.1 | C24—C23—H23B | 108.3 |
C1—C7—H7 | 118.1 | H23A—C23—H23B | 107.4 |
N1—C8—C9 | 106.6 (4) | C23—C24—H24A | 109.5 |
N1—C8—H8A | 110.4 | C23—C24—H24B | 109.5 |
C9—C8—H8A | 110.4 | H24A—C24—H24B | 109.5 |
N1—C8—H8B | 110.4 | C23—C24—H24C | 109.5 |
C9—C8—H8B | 110.4 | H24A—C24—H24C | 109.5 |
H8A—C8—H8B | 108.6 | H24B—C24—H24C | 109.5 |
N2—C9—C8 | 108.9 (4) | N4—C25—C26 | 114.9 (4) |
N2—C9—H9A | 109.9 | N4—C25—H25A | 108.6 |
C8—C9—H9A | 109.9 | C26—C25—H25A | 108.6 |
N2—C9—H9B | 109.9 | N4—C25—H25B | 108.6 |
C8—C9—H9B | 109.9 | C26—C25—H25B | 108.6 |
H9A—C9—H9B | 108.3 | H25A—C25—H25B | 107.5 |
N2—C10—C11 | 116.3 (4) | C25—C26—H26A | 109.5 |
N2—C10—H10A | 108.2 | C25—C26—H26B | 109.5 |
C11—C10—H10A | 108.2 | H26A—C26—H26B | 109.5 |
N2—C10—H10B | 108.2 | C25—C26—H26C | 109.5 |
C11—C10—H10B | 108.2 | H26A—C26—H26C | 109.5 |
H10A—C10—H10B | 107.4 | H26B—C26—H26C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C24—H24A···N10i | 0.96 | 2.49 | 3.407 (9) | 160 |
Symmetry code: (i) x−1, y, z. |