Dibromido-2κ2Br-bis­(4-methyl­pyridine-1κN){μ-2,2′-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato-1κ4O,N,N′,O′:2κ2O,O′}nickel(II)zinc(II)

Tatar Yıldırım, L.; Atakol, O.

doi:10.1107/S1600536807048581

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Dibromido-2κ²Br-bis(4-methylpyridine-1κN){μ-2,2′-[propane-1,3-diylbis(nitrilomethylidyne)]diphenolato-1κ⁴O,N,N′,O′:2κ²O,O′}nickel(II)zinc(II)

L. Tatar Yıldırım and O. Atakol

The molecule of the title compound, [NiZnBr₂(C₁₇H₁₆N₂O₂)(C₆H₇N)₂], contains a heterodinuclear arrangement. The two metal ions are bridged via phenol O atoms of the propane-1,3-diylbis(nitrilomethylidyne)]diphenolate (salpd²⁻) ligand. The two bridging O atoms of salpd²⁻ and two Br atoms constitute a distorted tetrahedral coordination environment around the Zn^II ion, while the Ni^II ion has a distorted octahedral coordination environment formed by two O and two N atoms of salpd²⁻ in the equatorial plane and two N atoms of two 4-methylpyridine ligands in the axial positions. In the crystal structure, weak intermolecular C—H

Br hydrogen bonds link the molecules into chains along the c axis. Weak intramolecular C—H

O and C—H

N hydrogen bonds are also present.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048581/hk2335sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048581/hk2335Isup2.hkl Contains datablock I

CCDC reference: 667126

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.029 Å
R factor = 0.066
wR factor = 0.206
Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Br1    -   Zn      ..      30.06 su
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C25
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C26
PLAT341_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         29
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H4     ..  H29B    ..       2.08 Ang.

Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.83 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.81 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Br2    -   Zn      ..       7.17 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         Zn
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           27.07
           From the CIF: _reflns_number_total               3379
           Count of symmetry unique reflns         3284
           Completeness (_total/calc)            102.89%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured        95
           Fraction of Friedel pairs measured     0.029
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn          (2)       1.99
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni          (2)       1.99

   0 ALERT level A = In general: serious problem
   6 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   2 ALERT type 5 Informative message, check

Comment top

Zinc and nickel elements are important essential rare elements for living beings (Bertini et al., 1994), in this respect the zinc and nickel compounds are very important in medicine. Some dinuclear zinc-nickel metal compounds of Schiff-base ligands have been studied in our laboratory (Tatar Yıldırım et al., 2007; Tatar, 2002; Tatar et al., 2002; Arıcı et al., 2001). We report herein the structure of the title compound, (I), a new hetero-dinuclear [ZnBr₂Ni(salpd^2-)(C₆H₇N)₂] complex [where salpd^2- is N,N'-bis- (salicylidene)-1,3-propanediamine].

In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles (Table 1) are generally in good agreement with the corresponding values in similar oxygen-bridged dinuclear complexes reported, previously (Tatar et al., 2007; Tatar, 2002; Tatar, Atakol et al., 2002; Svoboda et al., 2001; Arıcı et al., 2001). The two bridging O atoms of salpd2- ligand and two Br atoms constitute a distorted tetrahedral coordination environment around the Zn^II ion, while the Ni^II ion has a distorted octahedral coordination environment formed by two O and two N atoms of salpd^2- ligand in the equatorial plane and two N atoms of two methylpyridine ligands in the axial positions (Table 1). The Ni atom is -0.017 (2) Å away from the equatorial plane. The Zn···Ni distance is 3.062 (3) Å. The dihedral angle between (O1/Zn/O2) and (Br1/Zn/Br2) planes is 88.1 (3)°.

Rings B (Ni/O1/N1/C1/C6/C7), C (Ni/N1/N2/C8—C10) and D (Ni/O2/N2/C11/C12/C17) are not planar, having total puckering amplitudes, Q_T, of 0.190 (2), 1.143 (3) and 0.248 (2) Å, respectively [φ = 128.66 (5)°, θ = 92.56 (4)°; φ = 102.38 (6)°, θ = 85.87 (5)° and φ = 15.97 (6)°, θ = 43.44 (5)°, respectively] (Cremer & Pople, 1975). Rings B and D have flattened boat conformations, while ring A adopts a twisted conformation. Rings A (C1—C6), E (C12—C17), F (N3/C18—C22) and G (N4/C24—C28) are, of course, planar and the dihedral angles between them are A/E = 6.02 (3)° and F/G = 22.77 (2)°.

In the crystal structure, weak intermolecular C—H···Br hydrogen bonds (Table 2) link the molecules into chains along the c axis (Fig. 2); weak intramolecular C—H···O and C—H···N hydrogen bonds are also present.

Related literature top

For general background, see: Bertini et al. (1994); For related structures, see: Tatar et al. (2002); Tatar (2002); Tatar Yıldırım et al. (2007); Svoboda et al. (2001); Arıcı et al. (2001). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental top

For the preparation of the title compound, (I), N,N'-bis(salicylidene)-1,3 -propanediamine (1.410 g, 5 mmol) was dissolved in hot EtOH (50 ml), and then added to a solution of NiCl₂.6H₂O (1.185 g, 5 mmol) in hot water (30 ml) and ammonia (10 ml, 20%). The mixture was kept on the bench for 1–2 h. The pink precipitate was filtered and dried in an oven at 423 K. This complex (0.338 g, 1 mmol) was dissolved in hot dioxane (50 ml) and 4-methylpyridine (0.5 ml), and then added to a solution of ZnBr₂ (0.226 g, 1 mmol) in hot MeOH (20 ml). The resulting mixture was set aside for 2 d and the precipitated crystals were filtered and dried on air.

Structure description top

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Dibromido-2κ²Br-bis(4-methylpyridine-1κN){µ-2,2'-[propane-1,3- diylbis(nitrilomethylidyne)]diphenolato- 1κ⁴O,N,N',O':2κ²O,O'}nickel(II)zinc(II) top

Crystal data top

[NiZnBr₂(C₁₇H₁₆N₂O₂)(C₆H₇N)₂]	F(000) = 1504
M_r = 750.45	D_x = 1.674 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 15 reflections
a = 19.357 (3) Å	θ = 10.2–11.6°
b = 9.2130 (7) Å	µ = 4.16 mm⁻¹
c = 18.3269 (15) Å	T = 294 K
β = 114.382 (10)°	Prism, pink
V = 2976.9 (6) Å³	0.20 × 0.15 × 0.15 mm
Z = 4

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	R_int = 0.050
non–profiled ω scans	θ_max = 27.1°, θ_min = 2.3°
Absorption correction: ψ scan (North et al., 1968)	h = −24→0
T_min = 0.478, T_max = 0.536	k = −11→0
3381 measured reflections	l = −21→23
3379 independent reflections	3 standard reflections every 120 min
2118 reflections with I > 2σ(I)	intensity decay: 2%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters not refined
R[F² > 2σ(F²)] = 0.066	w = 1/[σ²(F_o²) + (0.1221P)² + 7.1119P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.206	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 1.30 e Å⁻³
3379 reflections	Δρ_min = −1.42 e Å⁻³
353 parameters	Absolute structure: Flack (1983), with 95 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.25 (7)
Secondary atom site location: difference Fourier map

Crystal data top

[NiZnBr₂(C₁₇H₁₆N₂O₂)(C₆H₇N)₂]	V = 2976.9 (6) Å³
M_r = 750.45	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 19.357 (3) Å	µ = 4.16 mm⁻¹
b = 9.2130 (7) Å	T = 294 K
c = 18.3269 (15) Å	0.20 × 0.15 × 0.15 mm
β = 114.382 (10)°

Data collection top

Enraf–Nonius TurboCAD-4 diffractometer	2118 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.050
T_min = 0.478, T_max = 0.536	3 standard reflections every 120 min
3381 measured reflections	intensity decay: 2%
3379 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	H-atom parameters not refined
wR(F²) = 0.206	Δρ_max = 1.30 e Å⁻³
S = 1.04	Δρ_min = −1.42 e Å⁻³
3379 reflections	Absolute structure: Flack (1983), with 95 Friedel pairs
353 parameters	Absolute structure parameter: 0.25 (7)

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	U_iso*/U_eq
Br1	0.9306 (8)	0.0500 (10)	0.8991 (6)	0.0763 (6)
Br2	0.82738 (13)	0.2500 (2)	0.99821 (11)	0.0761 (6)
Zn	0.94119 (8)	0.26209 (17)	0.97905 (8)	0.0440 (4)
Ni	1.05439 (11)	0.51344 (17)	1.01890 (11)	0.0402 (4)
O1	1.0376 (5)	0.3234 (10)	1.0686 (5)	0.041 (2)
O2	0.9577 (6)	0.4444 (11)	0.9314 (5)	0.045 (2)
N1	1.1532 (7)	0.5472 (14)	1.1188 (8)	0.052 (3)
N2	1.0548 (8)	0.6930 (12)	0.9518 (8)	0.051 (3)
N3	0.9881 (7)	0.6331 (12)	1.0703 (7)	0.044 (3)
N4	1.1205 (7)	0.3862 (13)	0.9650 (8)	0.050 (3)
C1	1.0756 (9)	0.2743 (14)	1.1395 (9)	0.045 (4)
C2	1.0492 (11)	0.1485 (18)	1.1622 (9)	0.059 (4)
H2	1.0062	0.1023	1.1255	0.07*
C3	1.0881 (12)	0.089 (2)	1.2422 (11)	0.076 (5)
H3	1.0708	0.0052	1.2575	0.091*
C4	1.1524 (12)	0.162 (2)	1.2954 (9)	0.068 (5)
H4	1.1773	0.1271	1.3475	0.081*
C5	1.1783 (10)	0.278 (2)	1.2733 (10)	0.064 (5)
H5	1.223	0.3193	1.3099	0.077*
C6	1.1416 (8)	0.3440 (16)	1.1959 (8)	0.046 (3)
C7	1.1783 (9)	0.4710 (17)	1.1806 (9)	0.049 (4)
H7	1.2248	0.4979	1.2206	0.059*
C8	1.1958 (9)	0.678 (2)	1.1167 (11)	0.071 (5)
H8A	1.2263	0.6562	1.0875	0.085*
H8B	1.2302	0.7026	1.1712	0.085*
C9	1.1480 (11)	0.8090 (19)	1.0793 (13)	0.075 (6)
H9A	1.1794	0.8951	1.0971	0.09*
H9B	1.1083	0.8161	1.0984	0.09*
C10	1.1114 (12)	0.807 (2)	0.9876 (13)	0.076 (5)
H10A	1.0875	0.9005	0.9687	0.091*
H10B	1.1511	0.7957	0.9687	0.091*
C11	1.0092 (11)	0.7073 (16)	0.8786 (10)	0.054 (4)
H11	1.0164	0.7906	0.8539	0.065*
C12	0.9484 (8)	0.6153 (16)	0.8280 (8)	0.043 (3)
C13	0.9113 (11)	0.6499 (18)	0.7485 (11)	0.061 (4)
H13	0.928	0.7312	0.7304	0.073*
C14	0.8516 (10)	0.574 (2)	0.6936 (11)	0.065 (4)
H14	0.8291	0.6001	0.6397	0.078*
C15	0.8280 (9)	0.461 (2)	0.7228 (9)	0.064 (5)
H15	0.7861	0.4092	0.688	0.077*
C16	0.8633 (9)	0.4150 (17)	0.8041 (9)	0.053 (4)
H16	0.8454	0.3349	0.822	0.063*
C17	0.9239 (9)	0.4915 (16)	0.8546 (8)	0.043 (4)
C18	0.9394 (9)	0.7358 (16)	1.0269 (10)	0.053 (4)
H18	0.9305	0.7469	0.9733	0.064*
C19	0.9030 (10)	0.8235 (18)	1.0583 (11)	0.060 (4)
H19	0.8689	0.8915	1.0254	0.073*
C20	0.9143 (11)	0.8160 (17)	1.1361 (12)	0.065 (5)
C21	0.9650 (11)	0.7132 (18)	1.1828 (10)	0.058 (4)
H21	0.9758	0.7046	1.237	0.07*
C22	1.0002 (9)	0.6211 (19)	1.1465 (9)	0.056 (4)
H22	1.033	0.5494	1.1774	0.067*
C23	0.8732 (15)	0.914 (3)	1.1757 (14)	0.101 (8)
H23A	0.8893	0.8872	1.2309	0.151*
H23B	0.8193	0.9012	1.148	0.151*
H23C	0.8857	1.014	1.1723	0.151*
C24	1.1542 (18)	0.266 (2)	0.9967 (17)	0.096 (8)
H24	1.1477	0.2289	1.0406	0.116*
C25	1.2003 (19)	0.189 (2)	0.9673 (16)	0.117 (11)
H25A	1.2247	0.105	0.9933	0.14*
C26	1.2093 (11)	0.2337 (17)	0.9045 (12)	0.064 (5)
C27	1.174 (2)	0.355 (4)	0.8725 (18)	0.165 (18)
H27	1.1786	0.3922	0.8272	0.096 (8)*
C28	1.133 (2)	0.427 (4)	0.904 (2)	0.064 (5)
H28	1.1107	0.5146	0.8802	0.225*
C29	1.2598 (13)	0.156 (2)	0.8728 (15)	0.091 (7)
H29A	1.2554	0.201	0.8238	0.137*
H29B	1.2446	0.0561	0.8628	0.137*
H29C	1.3115	0.1613	0.9116	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0643 (12)	0.1029 (15)	0.0706 (12)	−0.0122 (10)	0.0342 (9)	0.0016 (10)
Br2	0.0633 (12)	0.1009 (15)	0.0707 (12)	−0.0110 (10)	0.0341 (9)	0.0014 (10)
Zn	0.0447 (9)	0.0470 (10)	0.0406 (8)	−0.0113 (8)	0.0177 (7)	−0.0003 (7)
Ni	0.0399 (8)	0.0403 (10)	0.0443 (8)	−0.0041 (8)	0.0215 (6)	−0.0002 (8)
O1	0.035 (5)	0.043 (5)	0.037 (5)	0.000 (4)	0.008 (4)	0.003 (4)
O2	0.048 (6)	0.054 (6)	0.034 (5)	−0.008 (5)	0.017 (4)	0.008 (4)
N1	0.040 (7)	0.057 (7)	0.071 (9)	−0.018 (6)	0.034 (7)	−0.019 (7)
N2	0.064 (8)	0.032 (6)	0.075 (9)	−0.005 (6)	0.046 (8)	0.007 (6)
N3	0.037 (6)	0.048 (7)	0.058 (7)	−0.004 (5)	0.029 (5)	0.000 (6)
N4	0.043 (6)	0.045 (7)	0.068 (8)	−0.008 (6)	0.030 (6)	−0.005 (6)
C1	0.059 (9)	0.035 (8)	0.052 (9)	0.011 (7)	0.035 (8)	0.001 (6)
C2	0.073 (11)	0.055 (9)	0.045 (8)	0.005 (8)	0.022 (8)	0.005 (7)
C3	0.091 (13)	0.067 (11)	0.071 (11)	0.017 (11)	0.034 (11)	0.033 (10)
C4	0.075 (12)	0.074 (12)	0.033 (8)	0.024 (10)	0.002 (8)	0.010 (8)
C5	0.057 (11)	0.076 (12)	0.057 (10)	0.016 (9)	0.021 (8)	−0.013 (9)
C6	0.034 (7)	0.049 (8)	0.049 (8)	0.012 (6)	0.010 (6)	−0.008 (7)
C7	0.039 (8)	0.062 (9)	0.040 (8)	0.003 (7)	0.009 (6)	−0.014 (7)
C8	0.042 (9)	0.088 (13)	0.075 (11)	−0.024 (9)	0.017 (8)	0.001 (10)
C9	0.062 (11)	0.050 (10)	0.123 (17)	−0.031 (9)	0.049 (11)	−0.028 (10)
C10	0.068 (12)	0.071 (12)	0.091 (14)	−0.019 (10)	0.034 (11)	0.000 (11)
C11	0.079 (11)	0.033 (7)	0.068 (10)	0.006 (7)	0.049 (9)	0.011 (7)
C12	0.043 (8)	0.048 (8)	0.040 (7)	0.011 (7)	0.018 (6)	0.007 (6)
C13	0.074 (11)	0.052 (9)	0.069 (10)	0.033 (9)	0.042 (9)	0.033 (9)
C14	0.063 (11)	0.071 (11)	0.067 (11)	0.021 (9)	0.032 (9)	0.011 (9)
C15	0.045 (8)	0.089 (13)	0.045 (8)	0.011 (9)	0.005 (7)	0.004 (8)
C16	0.057 (9)	0.048 (9)	0.053 (8)	0.020 (7)	0.024 (8)	0.012 (7)
C17	0.044 (8)	0.055 (9)	0.029 (7)	0.026 (7)	0.016 (6)	0.011 (6)
C18	0.042 (8)	0.060 (9)	0.056 (9)	0.007 (7)	0.018 (7)	0.011 (7)
C19	0.060 (10)	0.051 (9)	0.085 (12)	0.020 (8)	0.044 (9)	0.008 (8)
C20	0.082 (13)	0.042 (9)	0.096 (13)	0.001 (9)	0.061 (11)	−0.003 (9)
C21	0.081 (12)	0.060 (10)	0.055 (9)	0.002 (9)	0.049 (9)	0.002 (8)
C22	0.050 (9)	0.069 (11)	0.053 (9)	0.007 (8)	0.026 (7)	0.012 (8)
C23	0.13 (2)	0.084 (15)	0.116 (18)	0.015 (14)	0.083 (17)	−0.027 (13)
C24	0.15 (2)	0.059 (12)	0.13 (2)	0.031 (12)	0.112 (19)	0.030 (11)
C25	0.21 (3)	0.063 (13)	0.14 (2)	0.067 (17)	0.13 (2)	0.033 (13)
C26	0.063 (11)	0.050 (9)	0.096 (13)	0.007 (8)	0.049 (10)	−0.007 (9)
C27	0.152 (2)	0.059 (12)	0.131 (2)	0.030 (12)	0.112 (19)	0.031 (11)
C28	0.065 (11)	0.051 (9)	0.096 (13)	0.007 (8)	0.049 (10)	−0.007 (9)
C29	0.084 (14)	0.079 (13)	0.127 (19)	0.001 (11)	0.060 (14)	−0.030 (13)

Geometric parameters (Å, º) top

Zn—Br1	2.400 (10)	C10—H10A	0.97
Zn—Br2	2.372 (3)	C10—H10B	0.97
Zn—O1	1.992 (9)	C11—H11	0.93
Zn—O2	1.979 (10)	C12—C13	1.37 (2)
Ni—O1	2.060 (10)	C12—C11	1.44 (2)
Ni—O2	2.000 (10)	C13—C14	1.37 (3)
Ni—N1	2.054 (14)	C13—H13	0.93
Ni—N2	2.063 (12)	C14—H14	0.93
Ni—N3	2.180 (12)	C15—C14	1.34 (3)
Ni—N4	2.243 (13)	C15—H15	0.93
O1—C1	1.283 (18)	C16—C15	1.42 (2)
O2—C17	1.355 (16)	C16—H16	0.93
N1—C8	1.47 (2)	C17—C16	1.35 (2)
N2—C10	1.46 (2)	C17—C12	1.40 (2)
N2—C11	1.27 (2)	C18—C19	1.35 (2)
N3—C18	1.341 (19)	C18—H18	0.93
N3—C22	1.321 (19)	C19—H19	0.93
N4—C24	1.29 (2)	C20—C19	1.35 (2)
N4—C28	1.29 (3)	C20—C23	1.57 (2)
C1—C2	1.40 (2)	C21—C20	1.38 (3)
C1—C6	1.42 (2)	C21—H21	0.93
C2—H2	0.93	C22—C21	1.41 (2)
C3—C2	1.45 (2)	C22—H22	0.93
C3—H3	0.93	C23—H23A	0.96
C4—C3	1.39 (3)	C23—H23B	0.96
C4—H4	0.93	C23—H23C	0.96
C5—C4	1.32 (3)	C24—C25	1.41 (3)
C5—H5	0.93	C24—H24	0.93
C6—C5	1.44 (2)	C25—H25A	0.93
C7—N1	1.25 (2)	C26—C25	1.30 (3)
C7—C6	1.45 (2)	C26—C27	1.31 (3)
C7—H7	0.93	C26—C29	1.51 (2)
C8—H8A	0.97	C27—C28	1.35 (3)
C8—H8B	0.97	C27—H27	0.93
C9—C8	1.50 (3)	C28—H28	0.93
C9—H9A	0.97	C29—H29A	0.96
C9—H9B	0.97	C29—H29B	0.96
C9—C10	1.53 (3)	C29—H29C	0.96

O2—Zn—O1	81.7 (4)	H9A—C9—H9B	107.6
O2—Zn—Br2	115.7 (3)	N2—C10—C9	114.9 (15)
O1—Zn—Br2	120.2 (3)	N2—C10—H10A	108.5
O2—Zn—Br1	114.2 (4)	C9—C10—H10A	108.5
O1—Zn—Br1	123.3 (4)	N2—C10—H10B	108.5
Br2—Zn—Br1	101.6 (3)	C9—C10—H10B	108.5
O2—Ni—N1	169.1 (5)	H10A—C10—H10B	107.5
O2—Ni—O1	79.5 (4)	N2—C11—C12	130.3 (14)
N1—Ni—O1	89.6 (4)	N2—C11—H11	114.9
O2—Ni—N2	90.6 (5)	C12—C11—H11	114.9
N1—Ni—N2	100.3 (6)	C13—C12—C17	117.2 (15)
O1—Ni—N2	170.1 (5)	C13—C12—C11	118.7 (15)
O2—Ni—N3	89.1 (5)	C17—C12—C11	124.2 (13)
N1—Ni—N3	92.1 (5)	C14—C13—C12	125.3 (16)
O1—Ni—N3	90.6 (4)	C14—C13—H13	117.4
N2—Ni—N3	90.0 (5)	C12—C13—H13	117.4
O2—Ni—N4	89.8 (5)	C15—C14—C13	115.3 (16)
N1—Ni—N4	88.9 (5)	C15—C14—H14	122.4
O1—Ni—N4	88.5 (4)	C13—C14—H14	122.4
N2—Ni—N4	90.8 (5)	C14—C15—C16	123.7 (17)
N3—Ni—N4	178.7 (5)	C14—C15—H15	118.1
C1—O1—Zn	133.3 (10)	C16—C15—H15	118.1
C1—O1—Ni	128.2 (9)	C17—C16—C15	117.8 (16)
Zn—O1—Ni	98.2 (4)	C17—C16—H16	121.1
C17—O2—Zn	129.3 (10)	C15—C16—H16	121.1
C17—O2—Ni	128.4 (10)	C16—C17—O2	117.0 (14)
Zn—O2—Ni	100.6 (4)	C16—C17—C12	120.6 (13)
C7—N1—C8	118.2 (14)	O2—C17—C12	122.4 (14)
C7—N1—Ni	126.4 (11)	N3—C18—C19	122.1 (16)
C8—N1—Ni	115.3 (11)	N3—C18—H18	118.9
C11—N2—C10	117.6 (14)	C19—C18—H18	118.9
C11—N2—Ni	122.7 (11)	C18—C19—C20	122.3 (16)
C10—N2—Ni	119.7 (12)	C18—C19—H19	118.8
C22—N3—C18	117.5 (14)	C20—C19—H19	118.8
C22—N3—Ni	122.4 (10)	C19—C20—C21	117.0 (15)
C18—N3—Ni	119.7 (10)	C19—C20—C23	124.5 (17)
C28—N4—C24	113.8 (17)	C21—C20—C23	118.5 (17)
C28—N4—Ni	124.6 (13)	C20—C21—C22	118.5 (15)
C24—N4—Ni	121.5 (13)	C20—C21—H21	120.7
O1—C1—C2	117.8 (14)	C22—C21—H21	120.7
O1—C1—C6	123.0 (14)	N3—C22—C21	122.5 (15)
C2—C1—C6	119.2 (14)	N3—C22—H22	118.8
C1—C2—C3	120.8 (17)	C21—C22—H22	118.8
C1—C2—H2	119.6	C20—C23—H23A	109.5
C3—C2—H2	119.6	C20—C23—H23B	109.5
C4—C3—C2	117.8 (17)	H23A—C23—H23B	109.5
C4—C3—H3	121.1	C20—C23—H23C	109.5
C2—C3—H3	121.1	H23A—C23—H23C	109.5
C5—C4—C3	121.3 (16)	H23B—C23—H23C	109.5
C5—C4—H4	119.4	N4—C24—C25	123 (2)
C3—C4—H4	119.4	N4—C24—H24	118.7
C4—C5—C6	123.7 (16)	C25—C24—H24	118.7
C4—C5—H5	118.2	C26—C25—C24	121.2 (19)
C6—C5—H5	118.2	C26—C25—H25A	119.4
C1—C6—C5	117.1 (15)	C24—C25—H25A	119.4
C1—C6—C7	125.9 (14)	C25—C26—C27	115.5 (17)
C5—C6—C7	116.8 (14)	C25—C26—C29	122.5 (18)
N1—C7—C6	126.1 (14)	C27—C26—C29	122 (2)
N1—C7—H7	116.9	C26—C27—C28	121 (2)
C6—C7—H7	116.9	C26—C27—H27	119.5
N1—C8—C9	115.1 (14)	C28—C27—H27	119.5
N1—C8—H8A	108.5	N4—C28—C27	126 (2)
C9—C8—H8A	108.5	N4—C28—H28	116.0
N1—C8—H8B	108.5	C27—C28—H28	117.2
C9—C8—H8B	108.5	C26—C29—H29A	109.5
H8A—C8—H8B	107.5	C26—C29—H29B	109.5
C8—C9—C10	114.3 (16)	H29A—C29—H29B	109.5
C8—C9—H9A	108.7	C26—C29—H29C	109.5
C10—C9—H9A	108.7	H29A—C29—H29C	109.5
C8—C9—H9B	108.7	H29B—C29—H29C	109.5
C10—C9—H9B	108.7

O2—Zn—O1—C1	173.2 (13)	Zn—O1—C1—C2	3 (2)
Br2—Zn—O1—C1	58.2 (13)	Ni—O1—C1—C2	174.3 (10)
Br1—Zn—O1—C1	−73.2 (13)	Zn—O1—C1—C6	−175.4 (10)
O2—Zn—O1—Ni	0.1 (5)	Ni—O1—C1—C6	−4 (2)
Br2—Zn—O1—Ni	−114.8 (3)	Zn—O2—C17—C16	9.8 (19)
Br1—Zn—O1—Ni	113.7 (4)	Ni—O2—C17—C16	172.0 (10)
O1—Zn—O2—C17	165.8 (12)	Zn—O2—C17—C12	−171.8 (10)
Br2—Zn—O2—C17	−74.7 (12)	Ni—O2—C17—C12	−10 (2)
Br1—Zn—O2—C17	42.9 (13)	C7—N1—C8—C9	−138.9 (17)
O1—Zn—O2—Ni	−0.1 (5)	Ni—N1—C8—C9	39 (2)
Br2—Zn—O2—Ni	119.5 (3)	C11—N2—C10—C9	162.5 (17)
Br1—Zn—O2—Ni	−123.0 (5)	Ni—N2—C10—C9	−20 (2)
O2—Ni—O1—C1	−173.7 (12)	C10—N2—C11—C12	−179.6 (17)
N1—Ni—O1—C1	7.3 (12)	Ni—N2—C11—C12	3 (2)
N3—Ni—O1—C1	−84.8 (12)	C22—N3—C18—C19	−1 (2)
N4—Ni—O1—C1	96.2 (12)	Ni—N3—C18—C19	−172.9 (13)
O2—Ni—O1—Zn	−0.1 (5)	C18—N3—C22—C21	−1 (2)
N1—Ni—O1—Zn	−179.1 (5)	Ni—N3—C22—C21	170.8 (12)
N3—Ni—O1—Zn	88.8 (5)	C28—N4—C24—C25	1 (4)
N4—Ni—O1—Zn	−90.2 (5)	Ni—N4—C24—C25	−176 (2)
N1—Ni—O2—C17	−161 (2)	C24—N4—C28—C27	2 (6)
O1—Ni—O2—C17	−165.9 (12)	Ni—N4—C28—C27	178 (4)
N2—Ni—O2—C17	13.3 (12)	O1—C1—C2—C3	−178.2 (15)
N3—Ni—O2—C17	103.3 (11)	C6—C1—C2—C3	0 (2)
N4—Ni—O2—C17	−77.5 (12)	O1—C1—C6—C5	179.5 (13)
N1—Ni—O2—Zn	5 (3)	C2—C1—C6—C5	1 (2)
O1—Ni—O2—Zn	0.1 (5)	O1—C1—C6—C7	−5 (2)
N2—Ni—O2—Zn	179.4 (5)	C2—C1—C6—C7	176.8 (14)
N3—Ni—O2—Zn	−90.6 (5)	C4—C3—C2—C1	0 (3)
N4—Ni—O2—Zn	88.6 (5)	C5—C4—C3—C2	−2 (3)
O2—Ni—N1—C7	−10 (4)	C6—C5—C4—C3	4 (3)
O1—Ni—N1—C7	−4.2 (13)	C1—C6—C5—C4	−3 (2)
N2—Ni—N1—C7	176.7 (13)	C7—C6—C5—C4	−179.2 (16)
N3—Ni—N1—C7	86.3 (13)	N1—C7—C6—C1	8 (3)
N4—Ni—N1—C7	−92.7 (13)	N1—C7—C6—C5	−176.2 (15)
O2—Ni—N1—C8	173 (2)	C6—C7—N1—C8	175.4 (15)
O1—Ni—N1—C8	178.4 (12)	C6—C7—N1—Ni	−2 (2)
N2—Ni—N1—C8	−0.6 (12)	C10—C9—C8—N1	−78 (2)
N3—Ni—N1—C8	−91.0 (12)	C8—C9—C10—N2	66 (2)
N4—Ni—N1—C8	89.9 (12)	C13—C12—C11—N2	−174.7 (16)
O2—Ni—N2—C11	−9.6 (13)	C17—C12—C11—N2	5 (3)
N1—Ni—N2—C11	169.2 (13)	C17—C12—C13—C14	1 (2)
N3—Ni—N2—C11	−98.7 (13)	C11—C12—C13—C14	−178.7 (16)
N4—Ni—N2—C11	80.2 (13)	C12—C13—C14—C15	2 (3)
O2—Ni—N2—C10	173.0 (14)	C16—C15—C14—C13	−3 (3)
N1—Ni—N2—C10	−8.2 (14)	C17—C16—C15—C14	1 (2)
N3—Ni—N2—C10	83.9 (14)	C16—C17—C12—C13	−4 (2)
N4—Ni—N2—C10	−97.2 (14)	O2—C17—C12—C13	178.2 (13)
O2—Ni—N3—C22	128.7 (12)	C16—C17—C12—C11	176.2 (14)
N1—Ni—N3—C22	−40.5 (12)	O2—C17—C12—C11	−2 (2)
O1—Ni—N3—C22	49.1 (12)	O2—C17—C16—C15	−178.8 (14)
N2—Ni—N3—C22	−140.8 (12)	C12—C17—C16—C15	3 (2)
O2—Ni—N3—C18	−59.6 (11)	N3—C18—C19—C20	1 (3)
N1—Ni—N3—C18	131.3 (11)	C21—C20—C19—C18	0 (3)
O1—Ni—N3—C18	−139.1 (11)	C23—C20—C19—C18	−179.5 (19)
N2—Ni—N3—C18	31.0 (12)	C22—C21—C20—C19	−1 (3)
O2—Ni—N4—C28	79 (3)	C22—C21—C20—C23	177.8 (18)
N1—Ni—N4—C28	−112 (3)	N3—C22—C21—C20	2 (3)
O1—Ni—N4—C28	159 (3)	N4—C24—C25—C26	−2 (5)
N2—Ni—N4—C28	−11 (3)	C27—C26—C25—C24	2 (5)
O2—Ni—N4—C24	−105.0 (19)	C29—C26—C25—C24	178 (3)
N1—Ni—N4—C24	64 (2)	C25—C26—C27—C28	0 (6)
O1—Ni—N4—C24	−25.5 (19)	C29—C26—C27—C28	−176 (4)
N2—Ni—N4—C24	164.4 (19)	C26—C27—C28—N4	−2 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Br2ⁱ	0.93	2.93	3.78 (2)	153
C23—H23A···Br1ⁱⁱ	0.96	2.91	3.79 (3)	153
C24—H24···O1	0.93	2.54	3.09 (4)	118
C28—H28···N2	0.93	2.60	3.18 (4)	121

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[NiZnBr₂(C₁₇H₁₆N₂O₂)(C₆H₇N)₂]
M_r	750.45
Crystal system, space group	Monoclinic, Cc
Temperature (K)	294
a, b, c (Å)	19.357 (3), 9.2130 (7), 18.3269 (15)
β (°)	114.382 (10)
V (Å³)	2976.9 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.16
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Enraf–Nonius TurboCAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.478, 0.536
No. of measured, independent and observed [I > 2σ(I)] reflections	3381, 3379, 2118
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.640

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.206, 1.04
No. of reflections	3379
No. of parameters	353
No. of restraints	?
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	1.30, −1.42
Absolute structure	Flack (1983), with 95 Friedel pairs
Absolute structure parameter	0.25 (7)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Zn—Br1	2.400 (10)	Ni—O2	2.000 (10)
Zn—Br2	2.372 (3)	Ni—N1	2.054 (14)
Zn—O1	1.992 (9)	Ni—N2	2.063 (12)
Zn—O2	1.979 (10)	Ni—N3	2.180 (12)
Ni—O1	2.060 (10)	Ni—N4	2.243 (13)

O2—Zn—O1	81.7 (4)	O1—Ni—N2	170.1 (5)
O2—Zn—Br2	115.7 (3)	O2—Ni—N3	89.1 (5)
O1—Zn—Br2	120.2 (3)	N1—Ni—N3	92.1 (5)
O2—Zn—Br1	114.2 (4)	O1—Ni—N3	90.6 (4)
O1—Zn—Br1	123.3 (4)	N2—Ni—N3	90.0 (5)
Br2—Zn—Br1	101.6 (3)	O2—Ni—N4	89.8 (5)
O2—Ni—N1	169.1 (5)	N1—Ni—N4	88.9 (5)
O2—Ni—O1	79.5 (4)	O1—Ni—N4	88.5 (4)
N1—Ni—O1	89.6 (4)	N2—Ni—N4	90.8 (5)
O2—Ni—N2	90.6 (5)	N3—Ni—N4	178.7 (5)
N1—Ni—N2	100.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···Br2ⁱ	0.93	2.93	3.78 (2)	153
C23—H23A···Br1ⁱⁱ	0.96	2.91	3.79 (3)	153
C24—H24···O1	0.93	2.54	3.09 (4)	118
C28—H28···N2	0.93	2.60	3.18 (4)	121

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2.

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