A new Ni–Zn heterodinuclear complex: [μ₂-bis­(salicyl­idene)propane-1,3-diaminato]dichloro­bis(N,N-dimethyl­formamide)nickel(II)zinc(II)

The title compound, [NiZn(C₁₇H₁₆N₂O₂)Cl₂(C₃H₇NO)₂], is a new heterodinuclear Ni^II–Zn^II complex. X-ray crystallographic analysis shows that the nickel(II) ion is in a distorted O₄N₂ octa­hedral environment, while the zinc(II) ion is in a distorted O₂Cl₂ tetra­hedral environment.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.036
• wR factor = 0.100
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C
SHFSU01_ALERT_2_C  The absolute value of parameter shift to su ratio > 0.05
            Absolute value of the parameter shift to su ratio given   0.052
            Additional refinement cycles may be required.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C8
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
PLAT301_ALERT_3_C Main Residue  Disorder .........................       5.00 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         45
            O4  -NI  -O3  -C18   164.00  3.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         50
            O3  -NI  -O4  -C21   -88.00  3.00   1.555   1.555   1.555   1.555

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           26.31
           From the CIF: _reflns_number_total               2792
           Count of symmetry unique reflns         2792
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

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

   1 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
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

[µ₂-bis(salicylidene)propane-1,3- diaminato]dichlorobis(N,N-dimethylformamide)nickel(II)}zinc(II)

Crystal data

[NiZn(C17H16N2O2)Cl2(C3H7NO)2]	F(000) = 1280.0
Mr = 621.53	Dx = 1.506 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 25 reflections
a = 10.4862 (3) Å	θ = 2.4–26.3°
b = 15.1938 (2) Å	µ = 1.79 mm^−1
c = 17.4233 (3) Å	T = 299 K
β = 99.010 (2)°	Prism, dark green
V = 2741.72 (10) Å^3	0.18 × 0.15 × 0.13 mm
Z = 4

Data collection

CAD-4 EXPRESS (Enraf–Nonius, 1993) diffractometer	Rint = 0.052
ω/2θ scans	θmax = 26.3°
Absorption correction: ψ scan (Fair, 1990)	h = −13→12
Tmin = 0.732, Tmax = 0.792	k = 0→18
2999 measured reflections	l = 0→21
2792 independent reflections	3 standard reflections every 120 min
2747 reflections with I > 2σ(I)	intensity decay: 0.1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0718P)^2 + 2.3115P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.052
2886 reflections	Δρmax = 0.75 e Å^−3
335 parameters	Δρmin = −0.62 e Å^−3
3 restraints	Absolute structure: Flack (1983), 0000 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn	0.54882 (4)	0.82110 (3)	0.42231 (3)	0.04352 (14)
Ni	0.39393 (4)	0.91682 (3)	0.53393 (3)	0.03637 (13)
Cl1	0.5581 (2)	0.67464 (10)	0.41298 (12)	0.0754 (4)
Cl2A	0.6656 (4)	0.8992 (2)	0.34814 (19)	0.0930 (10)	0.707 (6)
Cl2B	0.7466 (14)	0.8850 (10)	0.4031 (8)	0.0930 (10)	0.149 (4)
Cl2C	0.581 (2)	0.8988 (11)	0.3299 (9)	0.0930 (10)	0.145 (5)
O1	0.3681 (3)	0.86245 (19)	0.42678 (19)	0.0423 (6)
O2	0.5686 (3)	0.86253 (19)	0.53223 (19)	0.0421 (6)
O3	0.3261 (3)	0.8006 (2)	0.5843 (2)	0.0508 (7)
O4	0.4558 (3)	1.0368 (2)	0.4869 (2)	0.0537 (8)
N1	0.2077 (4)	0.9590 (2)	0.5173 (3)	0.0490 (9)
N2	0.4541 (4)	0.9624 (2)	0.6423 (2)	0.0477 (8)
N3	0.2821 (4)	0.6546 (2)	0.5819 (3)	0.0471 (8)
N4	0.4309 (5)	1.1366 (3)	0.3900 (3)	0.0594 (11)
C1	0.2636 (4)	0.8601 (3)	0.3733 (3)	0.0431 (9)
C2	0.2661 (6)	0.8170 (3)	0.3024 (4)	0.0553 (13)
H2A	0.3418	0.7896	0.2936	0.066*
C3	0.1602 (7)	0.8142 (4)	0.2462 (4)	0.0650 (16)
H3A	0.1645	0.7846	0.1999	0.078*
C4	0.0457 (6)	0.8553 (4)	0.2571 (4)	0.0698 (16)
H4A	−0.0262	0.8544	0.2183	0.084*
C5	0.0414 (5)	0.8961 (4)	0.3250 (4)	0.0667 (16)
H5A	−0.0356	0.9226	0.3325	0.080*
C6	0.1470 (5)	0.9008 (3)	0.3850 (3)	0.0475 (11)
C7	0.1265 (4)	0.9450 (3)	0.4566 (3)	0.0522 (11)
H7A	0.0432	0.9655	0.4578	0.063*
C8	0.1599 (6)	1.0062 (4)	0.5803 (4)	0.0749 (17)
H8A	0.0681	0.9948	0.5770	0.090*
H8B	0.1708	1.0689	0.5730	0.090*
C9	0.2257 (6)	0.9815 (4)	0.6599 (3)	0.0628 (13)
H9A	0.1753	1.0043	0.6976	0.075*
H9B	0.2259	0.9178	0.6641	0.075*
C10	0.3623 (6)	1.0137 (4)	0.6810 (4)	0.0686 (15)
H10A	0.3663	1.0751	0.6662	0.082*
H10B	0.3878	1.0099	0.7368	0.082*
C11	0.5650 (5)	0.9485 (3)	0.6821 (3)	0.0524 (11)
H11A	0.5779	0.9701	0.7326	0.063*
C12	0.6725 (5)	0.9032 (3)	0.6579 (3)	0.0492 (11)
C13	0.7869 (6)	0.9025 (5)	0.7134 (4)	0.0700 (18)
H13A	0.7863	0.9279	0.7619	0.084*
C14	0.8983 (7)	0.8651 (5)	0.6969 (5)	0.089 (2)
H14A	0.9734	0.8674	0.7332	0.106*
C15	0.8986 (8)	0.8241 (5)	0.6267 (6)	0.088 (2)
H15A	0.9734	0.7968	0.6163	0.105*
C16	0.7872 (6)	0.8231 (4)	0.5706 (5)	0.0702 (18)
H16A	0.7892	0.7959	0.5230	0.084*
C17	0.6721 (4)	0.8631 (3)	0.5855 (3)	0.0441 (9)
C18	0.3373 (4)	0.7264 (3)	0.5585 (3)	0.0462 (9)
H18A	0.3882	0.7198	0.5197	0.055*
C19	0.2016 (6)	0.6588 (4)	0.6401 (4)	0.0691 (15)
H19A	0.2000	0.7181	0.6590	0.104*
H19B	0.2347	0.6203	0.6822	0.104*
H19C	0.1157	0.6410	0.6184	0.104*
C20	0.2986 (6)	0.5692 (3)	0.5482 (5)	0.0728 (17)
H20A	0.3448	0.5757	0.5051	0.109*
H20B	0.2155	0.5436	0.5304	0.109*
H20C	0.3465	0.5316	0.5866	0.109*
C21	0.3947 (5)	1.0695 (3)	0.4280 (3)	0.0516 (10)
H21A	0.3155	1.0442	0.4087	0.062*
C22A	0.5738 (15)	1.1588 (11)	0.4002 (10)	0.093 (4)	0.568 (16)
H22A	0.5973	1.1737	0.3507	0.140*	0.568 (16)
H22B	0.6232	1.1088	0.4214	0.140*	0.568 (16)
H22C	0.5913	1.2078	0.4350	0.140*	0.568 (16)
C22B	0.513 (2)	1.2038 (15)	0.4349 (13)	0.093 (4)	0.432 (16)
H22D	0.4694	1.2594	0.4309	0.140*	0.432 (16)
H22E	0.5930	1.2093	0.4146	0.140*	0.432 (16)
H22F	0.5314	1.1864	0.4885	0.140*	0.432 (16)
C23	0.3516 (7)	1.1748 (4)	0.3215 (4)	0.0723 (16)
H23A	0.2733	1.1415	0.3090	0.108*
H23B	0.3984	1.1732	0.2783	0.108*
H23C	0.3310	1.2347	0.3321	0.108*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn	0.0487 (3)	0.0435 (3)	0.0408 (2)	0.0108 (2)	0.01474 (19)	0.0053 (2)
Ni	0.0388 (2)	0.0310 (2)	0.0410 (3)	0.00073 (19)	0.01188 (18)	0.0007 (2)
Cl1	0.0989 (11)	0.0483 (6)	0.0829 (11)	0.0175 (7)	0.0267 (8)	−0.0029 (6)
Cl2A	0.104 (2)	0.0960 (16)	0.0883 (17)	0.0293 (16)	0.0428 (16)	0.0368 (14)
Cl2B	0.104 (2)	0.0960 (16)	0.0883 (17)	0.0293 (16)	0.0428 (16)	0.0368 (14)
Cl2C	0.104 (2)	0.0960 (16)	0.0883 (17)	0.0293 (16)	0.0428 (16)	0.0368 (14)
O1	0.0373 (14)	0.0437 (15)	0.0455 (16)	0.0057 (11)	0.0048 (12)	−0.0040 (12)
O2	0.0402 (14)	0.0433 (15)	0.0431 (15)	0.0068 (12)	0.0072 (12)	0.0011 (12)
O3	0.0627 (19)	0.0365 (14)	0.0573 (19)	−0.0066 (13)	0.0219 (15)	0.0040 (14)
O4	0.0567 (18)	0.0426 (17)	0.060 (2)	−0.0083 (14)	0.0051 (15)	0.0155 (15)
N1	0.0443 (19)	0.0423 (19)	0.064 (2)	0.0055 (15)	0.0188 (17)	0.0041 (17)
N2	0.061 (2)	0.0378 (17)	0.048 (2)	−0.0102 (16)	0.0190 (18)	−0.0059 (15)
N3	0.0421 (18)	0.0389 (17)	0.061 (2)	−0.0020 (14)	0.0101 (16)	0.0076 (17)
N4	0.065 (3)	0.047 (2)	0.064 (3)	−0.0083 (18)	0.004 (2)	0.0176 (19)
C1	0.048 (2)	0.0304 (17)	0.049 (2)	−0.0040 (16)	0.0019 (18)	0.0081 (16)
C2	0.067 (3)	0.043 (3)	0.055 (3)	−0.006 (2)	0.005 (3)	−0.001 (2)
C3	0.083 (4)	0.056 (3)	0.052 (3)	−0.016 (3)	−0.004 (3)	0.003 (2)
C4	0.069 (4)	0.068 (3)	0.064 (4)	−0.020 (3)	−0.017 (3)	0.009 (3)
C5	0.040 (3)	0.064 (3)	0.093 (5)	−0.007 (2)	0.000 (3)	0.020 (3)
C6	0.038 (2)	0.043 (2)	0.061 (3)	−0.0051 (17)	0.005 (2)	0.011 (2)
C7	0.037 (2)	0.047 (2)	0.075 (3)	0.0070 (18)	0.014 (2)	0.009 (2)
C8	0.071 (3)	0.066 (3)	0.094 (4)	0.023 (3)	0.034 (3)	−0.006 (3)
C9	0.072 (3)	0.060 (3)	0.064 (3)	0.007 (2)	0.035 (3)	−0.006 (2)
C10	0.088 (4)	0.056 (3)	0.068 (3)	−0.002 (3)	0.030 (3)	−0.023 (3)
C11	0.068 (3)	0.050 (2)	0.040 (2)	−0.018 (2)	0.011 (2)	−0.0040 (19)
C12	0.053 (3)	0.047 (2)	0.046 (3)	−0.013 (2)	0.003 (2)	0.009 (2)
C13	0.064 (4)	0.076 (4)	0.062 (4)	−0.020 (3)	−0.014 (3)	0.015 (3)
C14	0.062 (4)	0.101 (5)	0.092 (5)	−0.005 (3)	−0.022 (3)	0.020 (4)
C15	0.058 (4)	0.107 (6)	0.092 (6)	0.022 (3)	−0.007 (4)	0.007 (4)
C16	0.049 (3)	0.077 (4)	0.081 (5)	0.016 (2)	0.001 (3)	0.008 (3)
C17	0.044 (2)	0.041 (2)	0.046 (2)	−0.0008 (16)	0.0053 (18)	0.0127 (17)
C18	0.049 (2)	0.037 (2)	0.054 (2)	−0.0027 (17)	0.0125 (19)	0.0114 (18)
C19	0.069 (3)	0.059 (3)	0.084 (4)	−0.015 (3)	0.028 (3)	0.012 (3)
C20	0.064 (3)	0.036 (2)	0.121 (6)	−0.005 (2)	0.026 (3)	0.003 (3)
C21	0.055 (3)	0.041 (2)	0.059 (3)	−0.0084 (18)	0.011 (2)	0.005 (2)
C22A	0.086 (8)	0.087 (9)	0.100 (9)	−0.035 (6)	−0.010 (6)	0.052 (7)
C22B	0.086 (8)	0.087 (9)	0.100 (9)	−0.035 (6)	−0.010 (6)	0.052 (7)
C23	0.084 (4)	0.071 (4)	0.061 (3)	0.001 (3)	0.009 (3)	0.026 (3)

Geometric parameters (Å, º)

Ni—Zn	3.0862 (7)	C7—H7A	0.9300
Zn—O2	1.996 (3)	C8—C9	1.496 (9)
Zn—O1	2.010 (3)	C8—H8A	0.9700
Zn—Cl2C	2.068 (13)	C8—H8B	0.9700
Zn—Cl1	2.2345 (16)	C9—C10	1.504 (9)
Zn—Cl2A	2.252 (3)	C9—H9A	0.9700
Zn—Cl2B	2.361 (15)	C9—H9B	0.9700
Ni—N2	2.017 (4)	C10—H10A	0.9700
Ni—O2	2.013 (3)	C10—H10B	0.9700
Ni—N1	2.032 (4)	C11—C12	1.439 (8)
Ni—O1	2.020 (3)	C11—H11A	0.9300
Ni—O3	2.143 (3)	C12—C17	1.400 (8)
Ni—O4	2.141 (3)	C12—C13	1.418 (8)
O1—C1	1.323 (5)	C13—C14	1.369 (12)
O2—C17	1.313 (5)	C13—H13A	0.9300
O3—C18	1.226 (6)	C14—C15	1.373 (13)
O4—C21	1.226 (6)	C14—H14A	0.9300
N1—C7	1.268 (7)	C15—C16	1.401 (11)
N1—C8	1.464 (7)	C15—H15A	0.9300
N2—C11	1.275 (7)	C16—C17	1.412 (8)
N2—C10	1.481 (7)	C16—H16A	0.9300
N3—C18	1.329 (6)	C18—H18A	0.9300
N3—C19	1.418 (8)	C19—H19A	0.9600
N3—C20	1.446 (7)	C19—H19B	0.9600
N4—C21	1.304 (6)	C19—H19C	0.9600
N4—C23	1.463 (7)	C20—H20A	0.9600
N4—C22B	1.48 (2)	C20—H20B	0.9600
N4—C22A	1.519 (15)	C20—H20C	0.9600
C1—C6	1.414 (7)	C21—H21A	0.9300
C1—C2	1.401 (8)	C22A—H22A	0.9600
C2—C3	1.361 (9)	C22A—H22B	0.9600
C2—H2A	0.9300	C22A—H22C	0.9600
C3—C4	1.393 (10)	C22B—H22D	0.9600
C3—H3A	0.9300	C22B—H22E	0.9600
C4—C5	1.342 (11)	C22B—H22F	0.9600
C4—H4A	0.9300	C23—H23A	0.9600
C5—C6	1.401 (8)	C23—H23B	0.9600
C5—H5A	0.9300	C23—H23C	0.9600
C6—C7	1.462 (8)
O2—Zn—O1	79.69 (13)	C6—C7—H7A	115.9
O2—Zn—Cl2C	124.2 (6)	N1—C8—C9	114.1 (4)
O1—Zn—Cl2C	97.1 (5)	N1—C8—H8A	108.7
O2—Zn—Cl1	112.63 (11)	C9—C8—H8A	108.7
O1—Zn—Cl1	111.50 (10)	N1—C8—H8B	108.7
Cl2C—Zn—Cl1	119.8 (5)	C9—C8—H8B	108.7
O2—Zn—Cl2A	113.60 (14)	H8A—C8—H8B	107.6
O1—Zn—Cl2A	117.28 (13)	C10—C9—C8	115.4 (5)
Cl2C—Zn—Cl2A	23.3 (5)	C10—C9—H9A	108.4
Cl1—Zn—Cl2A	116.67 (10)	C8—C9—H9A	108.4
O2—Zn—Cl2B	92.6 (4)	C10—C9—H9B	108.4
O1—Zn—Cl2B	137.0 (3)	C8—C9—H9B	108.4
Cl2C—Zn—Cl2B	53.0 (7)	H9A—C9—H9B	107.5
Cl1—Zn—Cl2B	110.5 (3)	N2—C10—C9	112.3 (4)
Cl2A—Zn—Cl2B	29.9 (3)	N2—C10—H10A	109.2
N2—Ni—O2	90.15 (15)	C9—C10—H10A	109.2
N2—Ni—N1	100.24 (18)	N2—C10—H10B	109.2
O2—Ni—N1	169.46 (16)	C9—C10—H10B	109.2
N2—Ni—O1	169.17 (14)	H10A—C10—H10B	107.9
O2—Ni—O1	79.02 (12)	N2—C11—C12	127.6 (4)
N1—Ni—O1	90.59 (16)	N2—C11—H11A	116.2
N2—Ni—O3	88.56 (15)	C12—C11—H11A	116.2
O2—Ni—O3	91.68 (13)	C17—C12—C13	119.6 (6)
N1—Ni—O3	86.86 (15)	C17—C12—C11	125.4 (5)
O1—Ni—O3	92.09 (13)	C13—C12—C11	115.0 (6)
N2—Ni—O4	89.83 (14)	C14—C13—C12	121.2 (7)
O2—Ni—O4	90.70 (13)	C14—C13—H13A	119.4
N1—Ni—O4	91.09 (15)	C12—C13—H13A	119.4
O1—Ni—O4	89.94 (14)	C13—C14—C15	119.8 (7)
O3—Ni—O4	177.13 (16)	C13—C14—H14A	120.1
C1—O1—Zn	130.2 (3)	C15—C14—H14A	120.1
C1—O1—Ni	129.7 (3)	C14—C15—C16	120.6 (8)
Zn—O1—Ni	99.95 (14)	C14—C15—H15A	119.7
C17—O2—Zn	129.1 (3)	C16—C15—H15A	119.7
C17—O2—Ni	129.8 (3)	C17—C16—C15	120.7 (8)
Zn—O2—Ni	100.67 (14)	C17—C16—H16A	119.6
C18—O3—Ni	123.4 (3)	C15—C16—H16A	119.6
C21—O4—Ni	121.1 (3)	O2—C17—C12	121.7 (4)
C7—N1—C8	116.3 (4)	O2—C17—C16	120.2 (5)
C7—N1—Ni	124.9 (4)	C12—C17—C16	118.1 (5)
C8—N1—Ni	118.8 (4)	O3—C18—N3	124.8 (5)
C11—N2—C10	116.3 (4)	O3—C18—H18A	117.6
C11—N2—Ni	125.2 (3)	N3—C18—H18A	117.6
C10—N2—Ni	118.5 (4)	N3—C19—H19A	109.5
C18—N3—C19	121.2 (5)	N3—C19—H19B	109.5
C18—N3—C20	121.7 (5)	H19A—C19—H19B	109.5
C19—N3—C20	117.0 (4)	N3—C19—H19C	109.5
C21—N4—C23	123.4 (5)	H19A—C19—H19C	109.5
C21—N4—C22B	117.6 (8)	H19B—C19—H19C	109.5
C23—N4—C22B	111.7 (8)	N3—C20—H20A	109.5
C21—N4—C22A	118.3 (6)	N3—C20—H20B	109.5
C23—N4—C22A	115.6 (6)	H20A—C20—H20B	109.5
C22B—N4—C22A	45.7 (10)	N3—C20—H20C	109.5
O1—C1—C6	121.7 (4)	H20A—C20—H20C	109.5
O1—C1—C2	120.4 (5)	H20B—C20—H20C	109.5
C6—C1—C2	117.9 (5)	O4—C21—N4	125.9 (5)
C3—C2—C1	121.6 (6)	O4—C21—H21A	117.0
C3—C2—H2A	119.2	N4—C21—H21A	117.0
C1—C2—H2A	119.2	N4—C22A—H22A	109.5
C2—C3—C4	120.7 (6)	N4—C22A—H22B	109.5
C2—C3—H3A	119.6	N4—C22A—H22C	109.5
C4—C3—H3A	119.6	N4—C22B—H22D	109.5
C5—C4—C3	118.4 (5)	N4—C22B—H22E	109.5
C5—C4—H4A	120.8	H22D—C22B—H22E	109.5
C3—C4—H4A	120.8	N4—C22B—H22F	109.5
C4—C5—C6	123.4 (6)	H22D—C22B—H22F	109.5
C4—C5—H5A	118.3	H22E—C22B—H22F	109.5
C6—C5—H5A	118.3	N4—C23—H23A	109.5
C5—C6—C1	118.0 (6)	N4—C23—H23B	109.5
C5—C6—C7	117.1 (5)	H23A—C23—H23B	109.5
C1—C6—C7	124.8 (4)	N4—C23—H23C	109.5
N1—C7—C6	128.2 (4)	H23A—C23—H23C	109.5
N1—C7—H7A	115.9	H23B—C23—H23C	109.5
O2—Zn—O1—C1	−177.7 (3)	N1—Ni—N2—C11	175.7 (4)
Cl2C—Zn—O1—C1	58.7 (7)	O1—Ni—N2—C11	−4.4 (10)
Cl1—Zn—O1—C1	−67.3 (3)	O3—Ni—N2—C11	89.2 (4)
Cl2A—Zn—O1—C1	71.0 (4)	O4—Ni—N2—C11	−93.2 (4)
Cl2B—Zn—O1—C1	99.7 (6)	O2—Ni—N2—C10	179.7 (4)
O2—Zn—O1—Ni	6.16 (13)	N1—Ni—N2—C10	−2.1 (4)
Cl2C—Zn—O1—Ni	−117.4 (6)	O1—Ni—N2—C10	177.8 (7)
Cl1—Zn—O1—Ni	116.57 (11)	O3—Ni—N2—C10	−88.6 (4)
Cl2A—Zn—O1—Ni	−105.19 (16)	O4—Ni—N2—C10	89.0 (4)
Cl2B—Zn—O1—Ni	−76.4 (6)	Zn—O1—C1—C6	−173.5 (3)
N2—Ni—O1—C1	179.6 (6)	Ni—O1—C1—C6	1.5 (6)
O2—Ni—O1—C1	177.7 (3)	Zn—O1—C1—C2	6.1 (6)
N1—Ni—O1—C1	−0.5 (3)	Ni—O1—C1—C2	−178.8 (3)
O3—Ni—O1—C1	86.4 (3)	O1—C1—C2—C3	−179.5 (5)
O4—Ni—O1—C1	−91.6 (3)	C6—C1—C2—C3	0.2 (7)
N2—Ni—O1—Zn	−4.2 (8)	C1—C2—C3—C4	0.7 (9)
O2—Ni—O1—Zn	−6.12 (13)	C2—C3—C4—C5	−1.3 (9)
N1—Ni—O1—Zn	175.69 (14)	C3—C4—C5—C6	1.1 (9)
O3—Ni—O1—Zn	−97.43 (15)	C4—C5—C6—C1	−0.2 (8)
O4—Ni—O1—Zn	84.60 (14)	C4—C5—C6—C7	−178.0 (5)
O1—Zn—O2—C17	−179.2 (4)	O1—C1—C6—C5	179.2 (4)
Cl2C—Zn—O2—C17	−87.6 (7)	C2—C1—C6—C5	−0.4 (7)
Cl1—Zn—O2—C17	71.7 (4)	O1—C1—C6—C7	−3.2 (7)
Cl2A—Zn—O2—C17	−63.8 (4)	C2—C1—C6—C7	177.2 (4)
Cl2B—Zn—O2—C17	−41.8 (5)	C8—N1—C7—C6	179.3 (5)
O1—Zn—O2—Ni	−6.20 (13)	Ni—N1—C7—C6	−3.2 (7)
Cl2C—Zn—O2—Ni	85.4 (7)	C5—C6—C7—N1	−178.1 (5)
Cl1—Zn—O2—Ni	−115.33 (11)	C1—C6—C7—N1	4.3 (8)
Cl2A—Zn—O2—Ni	109.20 (14)	C7—N1—C8—C9	149.1 (5)
Cl2B—Zn—O2—Ni	131.2 (3)	Ni—N1—C8—C9	−28.6 (7)
N2—Ni—O2—C17	−0.5 (4)	N1—C8—C9—C10	71.8 (7)
N1—Ni—O2—C17	−170.9 (7)	C11—N2—C10—C9	−143.1 (5)
O1—Ni—O2—C17	179.1 (4)	Ni—N2—C10—C9	34.9 (6)
O3—Ni—O2—C17	−89.1 (4)	C8—C9—C10—N2	−75.3 (6)
O4—Ni—O2—C17	89.3 (4)	C10—N2—C11—C12	−178.0 (5)
N2—Ni—O2—Zn	−173.46 (14)	Ni—N2—C11—C12	4.2 (7)
N1—Ni—O2—Zn	16.1 (9)	N2—C11—C12—C17	−2.4 (8)
O1—Ni—O2—Zn	6.18 (13)	N2—C11—C12—C13	176.3 (5)
O3—Ni—O2—Zn	97.98 (15)	C17—C12—C13—C14	1.6 (9)
O4—Ni—O2—Zn	−83.63 (15)	C11—C12—C13—C14	−177.2 (6)
N2—Ni—O3—C18	−140.0 (4)	C12—C13—C14—C15	−2.7 (11)
O2—Ni—O3—C18	−49.9 (4)	C13—C14—C15—C16	2.4 (13)
N1—Ni—O3—C18	119.7 (4)	C14—C15—C16—C17	−0.9 (12)
O1—Ni—O3—C18	29.2 (4)	Zn—O2—C17—C12	173.1 (3)
O4—Ni—O3—C18	164 (3)	Ni—O2—C17—C12	2.1 (6)
N2—Ni—O4—C21	−143.8 (4)	Zn—O2—C17—C16	−6.5 (6)
O2—Ni—O4—C21	126.1 (4)	Ni—O2—C17—C16	−177.5 (4)
N1—Ni—O4—C21	−43.5 (4)	C13—C12—C17—O2	−179.7 (4)
O1—Ni—O4—C21	47.1 (4)	C11—C12—C17—O2	−1.1 (7)
O3—Ni—O4—C21	−88 (3)	C13—C12—C17—C16	−0.1 (7)
N2—Ni—N1—C7	−178.8 (4)	C11—C12—C17—C16	178.6 (5)
O2—Ni—N1—C7	−8.5 (11)	C15—C16—C17—O2	179.4 (6)
O1—Ni—N1—C7	1.2 (4)	C15—C16—C17—C12	−0.3 (9)
O3—Ni—N1—C7	−90.8 (4)	Ni—O3—C18—N3	−170.9 (4)
O4—Ni—N1—C7	91.2 (4)	C19—N3—C18—O3	0.9 (8)
N2—Ni—N1—C8	−1.4 (4)	C20—N3—C18—O3	179.4 (5)
O2—Ni—N1—C8	168.9 (7)	Ni—O4—C21—N4	−172.2 (4)
O1—Ni—N1—C8	178.7 (4)	C23—N4—C21—O4	−177.7 (6)
O3—Ni—N1—C8	86.6 (4)	C22B—N4—C21—O4	−30.3 (15)
O4—Ni—N1—C8	−91.4 (4)	C22A—N4—C21—O4	21.8 (13)
O2—Ni—N2—C11	−2.5 (4)