The title compounds, {4,4'-dibromo-2,2'-[1,3-propanediylbis(nitrilomethylidyne-N)]diphenolato-O,O'}nickel(II), [Ni(C17H14Br2N2O2)], and {4,4'-dichloro-2,2'-[1,3-propanediylbis(nitrilomethylidyne-N)]diphenolato-O,O'}copper(II), [Cu(C17H14Cl2N2O2)], lie on crystallographic twofold axes. In both structures, the metal coordination sphere is a tetrahedrally distorted square plane formed by the four-coordinate N2O2 donor set of the Schiff base imine-phenol ligands. In the Ni compound, the Ni-O and Ni-N distances are 1.908 (3) and 1.959 (4) Å, respectively, while in the Cu compound, the Cu-O and Cu-N distances are 1.907 (2) and 1.960 (2) Å, respectively. The two Schiff base moieties, which themselves are nearly planar, are inclined at an angle of 29.26 (7)° for the Ni compound and 29.26 (5)° for the Cu compound.
Supporting information
CCDC references: 153869; 153870
For both compounds, data collection: CAD-4 Diffractometer Control Software (Enraf-Nonius, 1993); cell refinement: CAD-4 Diffractometer Control Software; data reduction: REDU4 (Stoe & Cie, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).
Crystal data top
[Ni(C17H14Br2N2O2)] | F(000) = 976 |
Mr = 496.83 | Dx = 1.985 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.466 (3) Å | Cell parameters from 25 reflections |
b = 8.167 (1) Å | θ = 2.7–13.3° |
c = 9.495 (3) Å | µ = 5.99 mm−1 |
β = 93.07 (2)° | T = 293 K |
V = 1662.2 (6) Å3 | Needle, dark blue |
Z = 4 | 0.40 × 0.05 × 0.03 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | 1016 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
ω–2θ scans | h = −26→26 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→0 |
Tmin = 0.75, Tmax = 0.84 | l = −11→3 |
2249 measured reflections | 3 standard reflections every 120 min |
1628 independent reflections | intensity decay: 2.0% |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0349P)2 + 4.1291P] where P = (Fo2 + 2Fc2)/3 |
1628 reflections | (Δ/σ)max < 0.001 |
114 parameters | Δρmax = 0.71 e Å−3 |
1 restraint | Δρmin = −0.38 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 | Occ. (<1) |
Ni1 | 0.5000 | 0.01666 (9) | 0.2500 | 0.0343 (2) | |
Br1 | 0.26976 (3) | 0.25243 (7) | −0.31466 (6) | 0.0653 (2) | |
O1 | 0.44154 (14) | 0.1858 (4) | 0.2007 (3) | 0.0443 (8) | |
N1 | 0.45946 (17) | −0.1417 (4) | 0.1200 (4) | 0.0426 (9) | |
C1 | 0.40088 (19) | 0.1893 (5) | 0.0941 (5) | 0.0372 (10) | |
C2 | 0.3642 (2) | 0.3315 (6) | 0.0701 (5) | 0.0463 (11) | |
H2 | 0.3670 | 0.4164 | 0.1354 | 0.056* | |
C3 | 0.3248 (2) | 0.3469 (6) | −0.0469 (5) | 0.0476 (12) | |
H3 | 0.3014 | 0.4419 | −0.0604 | 0.057* | |
C4 | 0.3195 (2) | 0.2223 (6) | −0.1454 (5) | 0.0446 (11) | |
C5 | 0.35041 (19) | 0.0772 (6) | −0.1216 (5) | 0.0415 (11) | |
H5 | 0.3446 | −0.0087 | −0.1853 | 0.050* | |
C6 | 0.39094 (19) | 0.0575 (5) | −0.0010 (4) | 0.0372 (10) | |
C7 | 0.4187 (2) | −0.1009 (5) | 0.0216 (5) | 0.0410 (11) | |
H7 | 0.4060 | −0.1829 | −0.0416 | 0.049* | |
C8 | 0.4750 (3) | −0.3182 (6) | 0.1268 (6) | 0.0656 (16) | |
H8A | 0.4422 | −0.3825 | 0.0794 | 0.098* | 0.50 |
H8B | 0.5139 | −0.3403 | 0.0828 | 0.098* | 0.50 |
H8C | 0.4372 | −0.3782 | 0.1438 | 0.098* | 0.50 |
H8D | 0.4891 | −0.3536 | 0.0364 | 0.098* | 0.50 |
C9 | 0.4803 (4) | −0.3760 (10) | 0.2739 (8) | 0.043 (2) | 0.50 |
H9A | 0.4403 | −0.3575 | 0.3138 | 0.064* | 0.50 |
H9B | 0.4859 | −0.4937 | 0.2698 | 0.064* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0430 (4) | 0.0248 (4) | 0.0342 (4) | 0.000 | −0.0050 (3) | 0.000 |
Br1 | 0.0626 (3) | 0.0788 (4) | 0.0522 (3) | 0.0079 (3) | −0.0189 (2) | 0.0031 (3) |
O1 | 0.0536 (19) | 0.0359 (16) | 0.0417 (18) | 0.0043 (14) | −0.0123 (15) | −0.0032 (14) |
N1 | 0.054 (2) | 0.032 (2) | 0.041 (2) | −0.0004 (17) | −0.0037 (19) | −0.0011 (17) |
C1 | 0.037 (2) | 0.040 (2) | 0.035 (2) | −0.0031 (19) | 0.004 (2) | 0.004 (2) |
C2 | 0.048 (3) | 0.042 (3) | 0.049 (3) | 0.004 (2) | 0.000 (2) | −0.003 (2) |
C3 | 0.043 (3) | 0.049 (3) | 0.050 (3) | 0.009 (2) | −0.001 (2) | 0.002 (3) |
C4 | 0.033 (2) | 0.057 (3) | 0.043 (3) | 0.000 (2) | −0.003 (2) | 0.001 (2) |
C5 | 0.042 (3) | 0.046 (3) | 0.036 (3) | −0.005 (2) | 0.002 (2) | −0.005 (2) |
C6 | 0.038 (2) | 0.041 (3) | 0.033 (2) | −0.0041 (19) | 0.0002 (19) | −0.002 (2) |
C7 | 0.051 (3) | 0.035 (2) | 0.037 (3) | −0.009 (2) | 0.002 (2) | −0.005 (2) |
C8 | 0.106 (5) | 0.030 (3) | 0.060 (4) | 0.013 (3) | −0.001 (3) | −0.004 (3) |
C9 | 0.048 (6) | 0.033 (5) | 0.049 (6) | −0.007 (4) | 0.014 (5) | 0.004 (4) |
Geometric parameters (Å, º) top
Ni1—O1i | 1.908 (3) | C3—H3 | 0.9300 |
Ni1—O1 | 1.908 (3) | C4—C5 | 1.371 (6) |
Ni1—N1 | 1.959 (4) | C5—C6 | 1.410 (6) |
Ni1—N1i | 1.959 (4) | C5—H5 | 0.9300 |
Br1—C4 | 1.897 (4) | C6—C7 | 1.436 (6) |
O1—C1 | 1.300 (5) | C7—H7 | 0.9300 |
O1—Ni1i | 1.908 (3) | C8—C9 | 1.473 (7) |
N1—C7 | 1.289 (6) | C8—H8A | 0.9700 |
N1—C8 | 1.480 (6) | C8—H8B | 0.9700 |
N1—Ni1i | 1.959 (4) | C8—H8C | 0.9700 |
C1—C2 | 1.415 (6) | C8—H8D | 0.9700 |
C1—C6 | 1.414 (6) | C9—C8i | 1.390 (10) |
C2—C3 | 1.365 (6) | C9—H8C | 1.5041 |
C2—H2 | 0.9300 | C9—H9A | 0.9700 |
C3—C4 | 1.383 (6) | C9—H9B | 0.9700 |
| | | |
O1i—Ni1—O1 | 87.23 (18) | C1—C6—C7 | 122.9 (4) |
O1i—Ni1—N1 | 153.75 (14) | N1—C7—C6 | 127.0 (4) |
O1—Ni1—N1 | 93.39 (14) | N1—C7—H7 | 116.5 |
O1i—Ni1—N1i | 93.39 (14) | C6—C7—H7 | 116.5 |
O1—Ni1—N1i | 153.75 (14) | C9—C8—N1 | 111.0 (5) |
N1—Ni1—N1i | 97.4 (2) | C9—C8—H8A | 106.5 |
C1—O1—Ni1i | 127.8 (3) | N1—C8—H8A | 110.5 |
C1—O1—Ni1 | 127.8 (3) | C9—C8—H8B | 108.9 |
C7—N1—C8 | 115.2 (4) | N1—C8—H8B | 111.1 |
C7—N1—Ni1i | 123.2 (3) | H8A—C8—H8B | 108.6 |
C8—N1—Ni1i | 121.6 (3) | C9—C8—H8C | 72.7 |
C7—N1—Ni1 | 123.2 (3) | N1—C8—H8C | 108.0 |
C8—N1—Ni1 | 121.6 (3) | H8A—C8—H8C | 37.8 |
O1—C1—C2 | 119.2 (4) | H8B—C8—H8C | 136.5 |
O1—C1—C6 | 123.5 (4) | C9—C8—H8D | 137.0 |
C2—C1—C6 | 117.3 (4) | N1—C8—H8D | 109.4 |
C3—C2—C1 | 121.5 (4) | H8A—C8—H8D | 71.4 |
C3—C2—H2 | 119.3 | H8B—C8—H8D | 41.1 |
C1—C2—H2 | 119.3 | H8C—C8—H8D | 107.5 |
C2—C3—C4 | 120.5 (4) | C8i—C9—C8 | 123.4 (7) |
C2—C3—H3 | 119.7 | C8i—C9—H8C | 158.9 |
C4—C3—H3 | 119.7 | C8—C9—H8C | 38.0 |
C5—C4—C3 | 120.2 (4) | C8i—C9—H9A | 106.0 |
C5—C4—Br1 | 119.8 (4) | C8—C9—H9A | 107.2 |
C3—C4—Br1 | 120.0 (3) | H8C—C9—H9A | 78.6 |
C4—C5—C6 | 120.3 (4) | C8i—C9—H9B | 106.4 |
C4—C5—H5 | 119.9 | C8—C9—H9B | 106.4 |
C6—C5—H5 | 119.9 | H8C—C9—H9B | 91.6 |
C5—C6—C1 | 119.9 (4) | H9A—C9—H9B | 106.5 |
C5—C6—C7 | 117.2 (4) | | |
| | | |
O1i—Ni1—O1—C1 | 140.6 (4) | C3—C4—C5—C6 | −4.1 (7) |
N1—Ni1—O1—C1 | −13.2 (4) | Br1—C4—C5—C6 | 175.6 (3) |
N1i—Ni1—O1—C1 | −127.4 (4) | C4—C5—C6—C1 | −1.5 (6) |
O1i—Ni1—N1—C7 | −76.2 (5) | C4—C5—C6—C7 | 176.3 (4) |
O1—Ni1—N1—C7 | 14.4 (4) | O1—C1—C6—C5 | −173.7 (4) |
N1i—Ni1—N1—C7 | 170.4 (4) | C2—C1—C6—C5 | 6.2 (6) |
O1i—Ni1—N1—C8 | 102.3 (5) | O1—C1—C6—C7 | 8.7 (7) |
O1—Ni1—N1—C8 | −167.1 (4) | C2—C1—C6—C7 | −171.5 (4) |
N1i—Ni1—N1—C8 | −11.1 (3) | C8—N1—C7—C6 | 173.8 (5) |
Ni1i—O1—C1—C2 | −175.8 (3) | Ni1i—N1—C7—C6 | −7.5 (7) |
Ni1—O1—C1—C2 | −175.8 (3) | Ni1—N1—C7—C6 | −7.5 (7) |
Ni1i—O1—C1—C6 | 4.1 (6) | C5—C6—C7—N1 | 175.8 (4) |
Ni1—O1—C1—C6 | 4.1 (6) | C1—C6—C7—N1 | −6.6 (7) |
O1—C1—C2—C3 | 174.3 (4) | C7—N1—C8—C9 | −138.5 (6) |
C6—C1—C2—C3 | −5.6 (7) | Ni1i—N1—C8—C9 | 42.8 (7) |
C1—C2—C3—C4 | 0.3 (7) | Ni1—N1—C8—C9 | 42.8 (7) |
C2—C3—C4—C5 | 4.7 (7) | N1—C8—C9—C8i | −63.1 (8) |
C2—C3—C4—Br1 | −174.9 (4) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |
Crystal data top
[Cu(C17H14Cl2N2O2)] | F(000) = 836 |
Mr = 412.74 | Dx = 1.706 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.022 (3) Å | Cell parameters from 25 reflections |
b = 8.140 (2) Å | θ = 1.9–15.9° |
c = 9.416 (3) Å | µ = 1.70 mm−1 |
β = 94.06 (2)° | T = 293 K |
V = 1607.2 (7) Å3 | Needle, blue |
Z = 4 | 0.30 × 0.08 × 0.08 mm |
Data collection top
Enraf-Nonius CAD4 diffractometer | 1274 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 26.0°, θmin = 1.9° |
ω–2θ scans | h = −25→25 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→0 |
Tmin = 0.79, Tmax = 0.87 | l = −11→2 |
1946 measured reflections | 3 standard reflections every 90 min |
1568 independent reflections | intensity decay: 3.0% |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.4477P] where P = (Fo2 + 2Fc2)/3 |
1568 reflections | (Δ/σ)max < 0.001 |
114 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.51 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 | Occ. (<1) |
Cu1 | 0.5000 | 0.01949 (5) | 0.2500 | 0.0383 (2) | |
Cl1 | 0.26844 (4) | 0.25493 (13) | −0.31366 (10) | 0.0677 (3) | |
O1 | 0.43986 (10) | 0.1888 (2) | 0.1998 (2) | 0.0437 (5) | |
N1 | 0.45778 (12) | −0.1393 (3) | 0.1182 (3) | 0.0414 (6) | |
C1 | 0.39829 (13) | 0.1928 (3) | 0.0911 (3) | 0.0385 (6) | |
C2 | 0.36059 (14) | 0.3360 (4) | 0.0647 (4) | 0.0451 (7) | |
H2 | 0.3632 | 0.4208 | 0.1310 | 0.054* | |
C3 | 0.32081 (14) | 0.3526 (4) | −0.0549 (4) | 0.0493 (7) | |
H3 | 0.2973 | 0.4485 | −0.0701 | 0.059* | |
C4 | 0.31524 (14) | 0.2263 (4) | −0.1545 (3) | 0.0460 (7) | |
C5 | 0.34610 (14) | 0.0812 (4) | −0.1291 (3) | 0.0443 (7) | |
H5 | 0.3397 | −0.0052 | −0.1932 | 0.053* | |
C6 | 0.38767 (13) | 0.0608 (4) | −0.0063 (3) | 0.0383 (6) | |
C7 | 0.41575 (14) | −0.0988 (3) | 0.0187 (3) | 0.0417 (7) | |
H7 | 0.4019 | −0.1817 | −0.0440 | 0.050* | |
C8 | 0.4736 (2) | −0.3162 (4) | 0.1249 (4) | 0.0666 (10) | |
H8A | 0.4401 | −0.3787 | 0.0734 | 0.100* | 0.50 |
H8B | 0.5129 | −0.3377 | 0.0803 | 0.100* | 0.50 |
H8C | 0.4347 | −0.3718 | 0.1475 | 0.100* | 0.50 |
H8D | 0.4841 | −0.3562 | 0.0324 | 0.100* | 0.50 |
C9 | 0.4800 (3) | −0.3741 (7) | 0.2732 (6) | 0.0434 (14) | 0.50 |
H9A | 0.4392 | −0.3549 | 0.3125 | 0.065* | 0.50 |
H9B | 0.4854 | −0.4924 | 0.2690 | 0.065* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0500 (3) | 0.0293 (3) | 0.0349 (3) | 0.000 | −0.0022 (2) | 0.000 |
Cl1 | 0.0667 (6) | 0.0803 (7) | 0.0528 (5) | 0.0089 (4) | −0.0193 (4) | 0.0026 (4) |
O1 | 0.0588 (12) | 0.0342 (10) | 0.0364 (11) | 0.0039 (9) | −0.0085 (9) | −0.0036 (8) |
N1 | 0.0562 (14) | 0.0299 (11) | 0.0376 (13) | −0.0006 (10) | 0.0001 (11) | −0.0023 (10) |
C1 | 0.0405 (14) | 0.0384 (14) | 0.0369 (15) | −0.0044 (11) | 0.0047 (12) | 0.0027 (12) |
C2 | 0.0491 (16) | 0.0395 (15) | 0.0467 (17) | 0.0027 (12) | 0.0033 (13) | −0.0019 (13) |
C3 | 0.0465 (16) | 0.0493 (17) | 0.0512 (19) | 0.0060 (13) | −0.0018 (14) | 0.0034 (15) |
C4 | 0.0386 (15) | 0.0571 (19) | 0.0418 (17) | −0.0010 (13) | −0.0010 (12) | 0.0010 (14) |
C5 | 0.0458 (16) | 0.0512 (16) | 0.0357 (15) | −0.0076 (13) | 0.0029 (13) | −0.0026 (13) |
C6 | 0.0404 (14) | 0.0397 (14) | 0.0351 (15) | −0.0048 (11) | 0.0053 (12) | 0.0002 (12) |
C7 | 0.0553 (17) | 0.0359 (14) | 0.0342 (15) | −0.0105 (13) | 0.0043 (13) | −0.0048 (12) |
C8 | 0.111 (3) | 0.0299 (15) | 0.059 (2) | 0.0099 (17) | 0.000 (2) | −0.0050 (15) |
C9 | 0.056 (4) | 0.030 (3) | 0.045 (4) | −0.002 (2) | 0.005 (3) | 0.002 (2) |
Geometric parameters (Å, º) top
Cu1—O1i | 1.907 (2) | C4—C5 | 1.361 (4) |
Cu1—O1 | 1.907 (2) | C5—C6 | 1.409 (4) |
Cu1—N1 | 1.960 (2) | C5—H5 | 0.9300 |
Cu1—N1i | 1.960 (2) | C6—C7 | 1.439 (4) |
Cl1—C4 | 1.749 (3) | C7—H7 | 0.9300 |
O1—C1 | 1.298 (4) | C8—C9 | 1.471 (6) |
N1—C7 | 1.284 (4) | C8—H8A | 0.9700 |
N1—C8 | 1.478 (4) | C8—H8B | 0.9700 |
C1—C6 | 1.420 (4) | C8—H8C | 0.9700 |
C1—C2 | 1.422 (4) | C8—H8D | 0.9700 |
C2—C3 | 1.361 (4) | C9—C8i | 1.401 (7) |
C2—H2 | 0.9300 | C9—H8C | 1.4651 |
C3—C4 | 1.391 (5) | C9—H9A | 0.9700 |
C3—H3 | 0.9300 | C9—H9B | 0.9700 |
| | | |
O1i—Cu1—O1 | 87.44 (12) | N1—C7—C6 | 127.2 (3) |
O1i—Cu1—N1 | 153.63 (10) | N1—C7—H7 | 116.4 |
O1—Cu1—N1 | 93.27 (10) | C6—C7—H7 | 116.4 |
O1i—Cu1—N1i | 93.27 (10) | N1—C8—C9 | 111.0 (3) |
O1—Cu1—N1i | 153.63 (10) | N1—C8—H8A | 109.7 |
N1—Cu1—N1i | 97.51 (14) | C9—C8—H8A | 108.7 |
C1—O1—Cu1 | 127.66 (18) | N1—C8—H8B | 110.7 |
C7—N1—C8 | 115.0 (3) | C9—C8—H8B | 109.2 |
C7—N1—Cu1 | 123.34 (19) | H8A—C8—H8B | 107.5 |
C8—N1—Cu1 | 121.7 (2) | N1—C8—H8C | 105.9 |
O1—C1—C6 | 123.8 (3) | C9—C8—H8C | 70.4 |
O1—C1—C2 | 119.6 (3) | H8A—C8—H8C | 43.4 |
C6—C1—C2 | 116.5 (3) | H8B—C8—H8C | 140.2 |
C3—C2—C1 | 121.9 (3) | N1—C8—H8D | 110.7 |
C3—C2—H2 | 119.1 | C9—C8—H8D | 137.2 |
C1—C2—H2 | 119.1 | H8A—C8—H8D | 65.1 |
C2—C3—C4 | 120.1 (3) | H8B—C8—H8D | 45.1 |
C2—C3—H3 | 119.9 | H8C—C8—H8D | 106.9 |
C4—C3—H3 | 119.9 | C8i—C9—C8 | 123.7 (4) |
C5—C4—C3 | 120.4 (3) | C8i—C9—H8C | 158.4 |
C5—C4—Cl1 | 119.9 (3) | C8—C9—H8C | 38.6 |
C3—C4—Cl1 | 119.6 (3) | C8i—C9—H9A | 106.0 |
C4—C5—C6 | 120.5 (3) | C8—C9—H9A | 106.6 |
C4—C5—H5 | 119.8 | H8C—C9—H9A | 76.4 |
C6—C5—H5 | 119.8 | C8i—C9—H9B | 106.5 |
C5—C6—C1 | 120.1 (3) | C8—C9—H9B | 106.4 |
C5—C6—C7 | 117.6 (3) | H8C—C9—H9B | 92.9 |
C1—C6—C7 | 122.2 (3) | H9A—C9—H9B | 106.5 |
| | | |
O1i—Cu1—O1—C1 | 139.6 (3) | C3—C4—C5—C6 | −4.5 (5) |
N1—Cu1—O1—C1 | −14.0 (2) | Cl1—C4—C5—C6 | 175.3 (2) |
N1i—Cu1—O1—C1 | −128.2 (3) | C4—C5—C6—C1 | −0.8 (4) |
O1i—Cu1—N1—C7 | −76.4 (3) | C4—C5—C6—C7 | 176.3 (3) |
O1—Cu1—N1—C7 | 14.5 (3) | O1—C1—C6—C5 | −173.8 (3) |
N1i—Cu1—N1—C7 | 170.4 (3) | C2—C1—C6—C5 | 5.9 (4) |
O1i—Cu1—N1—C8 | 102.3 (3) | O1—C1—C6—C7 | 9.3 (4) |
O1—Cu1—N1—C8 | −166.9 (3) | C2—C1—C6—C7 | −171.0 (3) |
N1i—Cu1—N1—C8 | −11.0 (2) | C8—N1—C7—C6 | 174.8 (3) |
Cu1—O1—C1—C6 | 4.7 (4) | Cu1—N1—C7—C6 | −6.5 (4) |
Cu1—O1—C1—C2 | −175.0 (2) | C5—C6—C7—N1 | 174.9 (3) |
O1—C1—C2—C3 | 173.6 (3) | C1—C6—C7—N1 | −8.1 (5) |
C6—C1—C2—C3 | −6.2 (4) | C7—N1—C8—C9 | −138.7 (4) |
C1—C2—C3—C4 | 1.1 (5) | Cu1—N1—C8—C9 | 42.6 (5) |
C2—C3—C4—C5 | 4.4 (5) | N1—C8—C9—C8i | −62.9 (6) |
C2—C3—C4—Cl1 | −175.4 (3) | | |
Symmetry code: (i) −x+1, y, −z+1/2. |