Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042882/sj2345sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042882/sj2345Isup2.hkl |
CCDC reference: 663571
1-naphthylamine (0.286 g, 2 mmol) and 3,5-Bibromo-2-hydroxy-benzaldehyde (0.560 g, 2 mmol) were mixed in ethanol and stirred for 30 min at room temperature to yield the Schiff base 2,4-dibromo-6-((naphthalen-1-ylimino)methyl)phenol. A mixture of this Schiff base (0.201 g, 0.5 mmol), CuSO4.5H2O2 (0.125 g, 0.5 mmol), phen (0.198 g 0.1 mmol,) and 6 drops of triethylamine in 5 ml e thanol and 5 ml acetonitrile was sealed in a 30 ml Teflon-lined stainless steel vessel, which was heated at 333 K for 7 days under autogenous pressure. On cooling to room temperature blue crystals of the title compound (I) were produced (yield: 53%, based on Cu).
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C).
Schiff bases play an important role in inorganic chemistry as they easily form stable complexes with most transition metal ions (Mostafa & Haifaa, 2007, Musie et al., 2003, Patel et al., 2006). We report herein the synthesis and crystal structure of (I), Fig 1, a mononuclear Cu(II) complex of the new Schiff base ligand 2,4-dibromo-6-((naphthalen-1-ylimino)methyl)phenolate and 1,10-phenanthroline. The copperII cation lies on a twofold axis and is coordinated by two N and two O atoms from the Schiff base and two N atoms from 1,10-phenanthroline, in a slightly distorted octahedral geometry.
In the crystal weak, non-classical C—H···Br hydrogen bonds link the molecules in rows along c, Fig 2.
For related complexes of Schiff bases with transition metal ions, see: Mostafa & Haifaa (2007); Musie et al. (2003); Patel et al. (2006).
For related literature, see: Mehmet et al. (2007).
Data collection: SMART (Bruker 2001); cell refinement: SAINT (Bruker 2001); data reduction: SAINT (Bruker 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 1997); software used to prepare material for publication: SHELXTL (Bruker 1997).
Fig. 1. A view of (I), showing 30% probability displacement ellipsoids. | |
Fig. 2. Crystal packing of (I) with H-bonds drawn as dashed lines. |
[Cu(C17H10Br2NO)2(C12H8N2)] | F(000) = 2068 |
Mr = 1051.90 | Dx = 1.750 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1985 reflections |
a = 20.288 (2) Å | θ = 2.8–20.6° |
b = 14.5052 (18) Å | µ = 4.59 mm−1 |
c = 15.227 (2) Å | T = 298 K |
β = 116.977 (2)° | Block, blue |
V = 3993.5 (9) Å3 | 0.38 × 0.19 × 0.17 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3513 independent reflections |
Radiation source: fine-focus sealed tube | 1877 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→24 |
Tmin = 0.274, Tmax = 0.509 | k = −16→17 |
10067 measured reflections | l = −17→18 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0811P)2] where P = (Fo2 + 2Fc2)/3 |
3513 reflections | (Δ/σ)max = 0.001 |
258 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
[Cu(C17H10Br2NO)2(C12H8N2)] | V = 3993.5 (9) Å3 |
Mr = 1051.90 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 20.288 (2) Å | µ = 4.59 mm−1 |
b = 14.5052 (18) Å | T = 298 K |
c = 15.227 (2) Å | 0.38 × 0.19 × 0.17 mm |
β = 116.977 (2)° |
Bruker SMART CCD area-detector diffractometer | 3513 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1877 reflections with I > 2σ(I) |
Tmin = 0.274, Tmax = 0.509 | Rint = 0.086 |
10067 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.95 e Å−3 |
3513 reflections | Δρmin = −0.73 e Å−3 |
258 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.5000 | 0.93455 (7) | 0.2500 | 0.0392 (4) | |
Br1 | 0.37169 (5) | 0.70105 (6) | 0.02414 (6) | 0.0636 (3) | |
Br2 | 0.62496 (6) | 0.47645 (6) | 0.17224 (8) | 0.0864 (4) | |
N1 | 0.6262 (3) | 0.9081 (4) | 0.2840 (4) | 0.0421 (15) | |
N2 | 0.4717 (3) | 1.0413 (4) | 0.1537 (4) | 0.0404 (15) | |
O1 | 0.4819 (3) | 0.8458 (3) | 0.1455 (3) | 0.0430 (12) | |
C1 | 0.6420 (4) | 0.8241 (5) | 0.2785 (5) | 0.0437 (19) | |
H1 | 0.6907 | 0.8064 | 0.3181 | 0.052* | |
C2 | 0.5920 (4) | 0.7527 (5) | 0.2168 (5) | 0.0398 (18) | |
C3 | 0.5152 (4) | 0.7679 (5) | 0.1568 (5) | 0.0404 (18) | |
C4 | 0.4749 (4) | 0.6892 (5) | 0.1040 (5) | 0.0435 (19) | |
C5 | 0.5061 (5) | 0.6039 (5) | 0.1086 (5) | 0.052 (2) | |
H5 | 0.4772 | 0.5543 | 0.0731 | 0.063* | |
C6 | 0.5824 (5) | 0.5933 (5) | 0.1682 (6) | 0.051 (2) | |
C7 | 0.6236 (5) | 0.6661 (5) | 0.2209 (5) | 0.049 (2) | |
H7 | 0.6741 | 0.6582 | 0.2605 | 0.058* | |
C8 | 0.6805 (4) | 0.9648 (5) | 0.3581 (6) | 0.0457 (19) | |
C9 | 0.7164 (5) | 0.9372 (5) | 0.4543 (6) | 0.061 (2) | |
H9 | 0.7083 | 0.8785 | 0.4719 | 0.073* | |
C10 | 0.7658 (6) | 0.9981 (7) | 0.5273 (7) | 0.085 (3) | |
H10 | 0.7919 | 0.9781 | 0.5921 | 0.101* | |
C11 | 0.7751 (5) | 1.0838 (7) | 0.5035 (8) | 0.087 (3) | |
H11 | 0.8062 | 1.1236 | 0.5528 | 0.104* | |
C12 | 0.7393 (5) | 1.1154 (5) | 0.4061 (8) | 0.066 (3) | |
C13 | 0.6910 (4) | 1.0555 (5) | 0.3300 (7) | 0.053 (2) | |
C14 | 0.6534 (5) | 1.0870 (6) | 0.2316 (7) | 0.066 (2) | |
H14 | 0.6228 | 1.0475 | 0.1816 | 0.079* | |
C15 | 0.6629 (7) | 1.1759 (8) | 0.2112 (10) | 0.097 (4) | |
H15 | 0.6373 | 1.1969 | 0.1467 | 0.116* | |
C16 | 0.7096 (7) | 1.2367 (7) | 0.2837 (12) | 0.102 (4) | |
H16 | 0.7158 | 1.2966 | 0.2669 | 0.122* | |
C17 | 0.7461 (6) | 1.2080 (7) | 0.3789 (10) | 0.088 (3) | |
H17 | 0.7760 | 1.2494 | 0.4272 | 0.105* | |
C18 | 0.4844 (4) | 1.1253 (4) | 0.1971 (5) | 0.0370 (17) | |
C19 | 0.4695 (4) | 1.2085 (5) | 0.1460 (6) | 0.049 (2) | |
C20 | 0.4396 (5) | 1.2025 (6) | 0.0433 (6) | 0.060 (2) | |
H20 | 0.4288 | 1.2559 | 0.0056 | 0.072* | |
C21 | 0.4263 (5) | 1.1177 (6) | −0.0020 (6) | 0.067 (3) | |
H21 | 0.4063 | 1.1134 | −0.0702 | 0.080* | |
C22 | 0.4434 (4) | 1.0386 (5) | 0.0560 (5) | 0.050 (2) | |
H22 | 0.4346 | 0.9814 | 0.0251 | 0.060* | |
C23 | 0.4850 (5) | 1.2925 (5) | 0.2001 (6) | 0.067 (3) | |
H23 | 0.4742 | 1.3484 | 0.1664 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0522 (8) | 0.0356 (7) | 0.0274 (7) | 0.000 | 0.0161 (6) | 0.000 |
Br1 | 0.0580 (6) | 0.0703 (6) | 0.0482 (5) | −0.0060 (5) | 0.0115 (4) | −0.0159 (4) |
Br2 | 0.0961 (9) | 0.0469 (6) | 0.0961 (8) | 0.0138 (5) | 0.0260 (7) | −0.0145 (5) |
N1 | 0.044 (4) | 0.039 (3) | 0.041 (4) | −0.002 (3) | 0.018 (3) | −0.005 (3) |
N2 | 0.042 (4) | 0.047 (4) | 0.032 (4) | −0.001 (3) | 0.017 (3) | 0.000 (3) |
O1 | 0.052 (3) | 0.042 (3) | 0.030 (3) | 0.003 (3) | 0.014 (2) | −0.002 (2) |
C1 | 0.046 (5) | 0.050 (5) | 0.035 (4) | −0.003 (4) | 0.018 (4) | −0.006 (3) |
C2 | 0.048 (5) | 0.041 (4) | 0.030 (4) | −0.006 (4) | 0.017 (4) | −0.006 (3) |
C3 | 0.058 (5) | 0.040 (4) | 0.027 (4) | −0.004 (4) | 0.023 (4) | −0.002 (3) |
C4 | 0.053 (5) | 0.048 (4) | 0.030 (4) | −0.002 (4) | 0.019 (4) | −0.001 (3) |
C5 | 0.078 (7) | 0.041 (4) | 0.035 (4) | −0.008 (5) | 0.023 (5) | −0.009 (3) |
C6 | 0.063 (6) | 0.041 (4) | 0.047 (5) | 0.004 (4) | 0.022 (4) | −0.001 (4) |
C7 | 0.056 (5) | 0.043 (4) | 0.042 (5) | 0.003 (4) | 0.019 (4) | 0.002 (3) |
C8 | 0.041 (5) | 0.046 (4) | 0.048 (5) | −0.003 (4) | 0.017 (4) | −0.007 (4) |
C9 | 0.064 (6) | 0.056 (5) | 0.047 (5) | 0.003 (5) | 0.011 (4) | −0.012 (4) |
C10 | 0.089 (8) | 0.077 (6) | 0.044 (6) | 0.012 (6) | −0.008 (5) | −0.021 (5) |
C11 | 0.059 (7) | 0.085 (7) | 0.087 (8) | 0.004 (6) | 0.008 (6) | −0.048 (6) |
C12 | 0.051 (6) | 0.045 (5) | 0.093 (8) | 0.005 (5) | 0.025 (6) | −0.026 (5) |
C13 | 0.041 (5) | 0.048 (5) | 0.074 (6) | −0.001 (4) | 0.028 (5) | −0.011 (4) |
C14 | 0.061 (6) | 0.066 (6) | 0.073 (7) | 0.003 (5) | 0.034 (5) | 0.008 (5) |
C15 | 0.098 (9) | 0.083 (8) | 0.141 (11) | 0.017 (7) | 0.083 (9) | 0.041 (8) |
C16 | 0.093 (10) | 0.056 (7) | 0.193 (15) | −0.004 (7) | 0.096 (11) | 0.016 (8) |
C17 | 0.066 (7) | 0.060 (7) | 0.145 (11) | −0.010 (6) | 0.056 (8) | −0.025 (7) |
C18 | 0.034 (4) | 0.035 (4) | 0.042 (4) | −0.002 (3) | 0.017 (4) | 0.001 (3) |
C19 | 0.048 (5) | 0.041 (4) | 0.059 (5) | 0.000 (4) | 0.026 (4) | 0.008 (4) |
C20 | 0.074 (6) | 0.060 (5) | 0.051 (5) | 0.011 (5) | 0.032 (5) | 0.022 (4) |
C21 | 0.091 (7) | 0.069 (6) | 0.035 (5) | 0.011 (5) | 0.024 (5) | 0.020 (4) |
C22 | 0.064 (5) | 0.054 (5) | 0.033 (4) | −0.001 (4) | 0.023 (4) | −0.001 (3) |
C23 | 0.076 (7) | 0.044 (4) | 0.081 (6) | 0.009 (5) | 0.036 (6) | 0.019 (4) |
Cu1—O1 | 1.948 (4) | C9—H9 | 0.9300 |
Cu1—O1i | 1.948 (4) | C10—C11 | 1.332 (13) |
Cu1—N2i | 2.029 (5) | C10—H10 | 0.9300 |
Cu1—N2 | 2.029 (5) | C11—C12 | 1.400 (13) |
Cu1—N1i | 2.402 (6) | C11—H11 | 0.9300 |
Cu1—N1 | 2.402 (6) | C12—C13 | 1.424 (11) |
Br1—C4 | 1.893 (8) | C12—C17 | 1.431 (13) |
Br2—C6 | 1.890 (7) | C13—C14 | 1.413 (11) |
N1—C1 | 1.273 (8) | C14—C15 | 1.361 (12) |
N1—C8 | 1.426 (9) | C14—H14 | 0.9300 |
N2—C22 | 1.330 (8) | C15—C16 | 1.394 (16) |
N2—C18 | 1.355 (8) | C15—H15 | 0.9300 |
O1—C3 | 1.288 (8) | C16—C17 | 1.360 (15) |
C1—C2 | 1.455 (9) | C16—H16 | 0.9300 |
C1—H1 | 0.9300 | C17—H17 | 0.9300 |
C2—C7 | 1.399 (9) | C18—C19 | 1.393 (9) |
C2—C3 | 1.421 (10) | C18—C18i | 1.438 (13) |
C3—C4 | 1.421 (9) | C19—C20 | 1.401 (10) |
C4—C5 | 1.377 (9) | C19—C23 | 1.424 (10) |
C5—C6 | 1.403 (11) | C20—C21 | 1.375 (10) |
C5—H5 | 0.9300 | C20—H20 | 0.9300 |
C6—C7 | 1.360 (10) | C21—C22 | 1.393 (10) |
C7—H7 | 0.9300 | C21—H21 | 0.9300 |
C8—C9 | 1.368 (10) | C22—H22 | 0.9300 |
C8—C13 | 1.429 (10) | C23—C23i | 1.357 (16) |
C9—C10 | 1.417 (11) | C23—H23 | 0.9300 |
O1—Cu1—O1i | 97.3 (3) | C8—C9—C10 | 120.0 (8) |
O1—Cu1—N2i | 169.1 (2) | C8—C9—H9 | 120.0 |
O1i—Cu1—N2i | 91.5 (2) | C10—C9—H9 | 120.0 |
O1—Cu1—N2 | 91.5 (2) | C11—C10—C9 | 120.4 (9) |
O1i—Cu1—N2 | 169.1 (2) | C11—C10—H10 | 119.8 |
N2i—Cu1—N2 | 80.5 (3) | C9—C10—H10 | 119.8 |
O1—Cu1—N1i | 86.0 (2) | C10—C11—C12 | 121.6 (8) |
O1i—Cu1—N1i | 81.9 (2) | C10—C11—H11 | 119.2 |
N2i—Cu1—N1i | 101.7 (2) | C12—C11—H11 | 119.2 |
N2—Cu1—N1i | 92.4 (2) | C11—C12—C13 | 119.8 (8) |
O1—Cu1—N1 | 81.9 (2) | C11—C12—C17 | 122.8 (10) |
O1i—Cu1—N1 | 86.0 (2) | C13—C12—C17 | 117.3 (10) |
N2i—Cu1—N1 | 92.4 (2) | C14—C13—C12 | 120.5 (8) |
N2—Cu1—N1 | 101.7 (2) | C14—C13—C8 | 122.2 (7) |
N1i—Cu1—N1 | 161.6 (3) | C12—C13—C8 | 117.3 (8) |
C1—N1—C8 | 118.5 (6) | C15—C14—C13 | 118.9 (10) |
C1—N1—Cu1 | 114.5 (5) | C15—C14—H14 | 120.5 |
C8—N1—Cu1 | 116.4 (4) | C13—C14—H14 | 120.5 |
C22—N2—C18 | 117.6 (6) | C14—C15—C16 | 122.3 (12) |
C22—N2—Cu1 | 128.5 (5) | C14—C15—H15 | 118.8 |
C18—N2—Cu1 | 113.9 (4) | C16—C15—H15 | 118.8 |
C3—O1—Cu1 | 125.3 (4) | C17—C16—C15 | 119.7 (10) |
N1—C1—C2 | 126.9 (7) | C17—C16—H16 | 120.1 |
N1—C1—H1 | 116.5 | C15—C16—H16 | 120.1 |
C2—C1—H1 | 116.5 | C16—C17—C12 | 121.2 (10) |
C7—C2—C3 | 120.9 (6) | C16—C17—H17 | 119.4 |
C7—C2—C1 | 116.0 (7) | C12—C17—H17 | 119.4 |
C3—C2—C1 | 123.1 (6) | N2—C18—C19 | 124.2 (6) |
O1—C3—C2 | 125.3 (6) | N2—C18—C18i | 115.9 (4) |
O1—C3—C4 | 119.8 (7) | C19—C18—C18i | 120.0 (4) |
C2—C3—C4 | 114.9 (7) | C18—C19—C20 | 116.4 (7) |
C5—C4—C3 | 124.1 (7) | C18—C19—C23 | 118.9 (7) |
C5—C4—Br1 | 117.6 (6) | C20—C19—C23 | 124.7 (7) |
C3—C4—Br1 | 118.4 (5) | C21—C20—C19 | 120.2 (7) |
C4—C5—C6 | 118.5 (7) | C21—C20—H20 | 119.9 |
C4—C5—H5 | 120.7 | C19—C20—H20 | 119.9 |
C6—C5—H5 | 120.7 | C20—C21—C22 | 118.9 (7) |
C7—C6—C5 | 119.9 (7) | C20—C21—H21 | 120.5 |
C7—C6—Br2 | 121.9 (6) | C22—C21—H21 | 120.5 |
C5—C6—Br2 | 118.2 (6) | N2—C22—C21 | 122.8 (7) |
C6—C7—C2 | 121.7 (7) | N2—C22—H22 | 118.6 |
C6—C7—H7 | 119.2 | C21—C22—H22 | 118.6 |
C2—C7—H7 | 119.2 | C23i—C23—C19 | 121.1 (4) |
C9—C8—N1 | 121.5 (7) | C23i—C23—H23 | 119.4 |
C9—C8—C13 | 120.8 (7) | C19—C23—H23 | 119.4 |
N1—C8—C13 | 117.4 (7) | ||
O1—Cu1—N1—C1 | −42.1 (5) | Br2—C6—C7—C2 | 179.3 (5) |
O1i—Cu1—N1—C1 | 55.8 (5) | C3—C2—C7—C6 | −0.3 (11) |
N2i—Cu1—N1—C1 | 147.2 (5) | C1—C2—C7—C6 | 178.7 (6) |
N2—Cu1—N1—C1 | −132.0 (5) | C1—N1—C8—C9 | −49.5 (10) |
N1i—Cu1—N1—C1 | 7.1 (5) | Cu1—N1—C8—C9 | 93.2 (8) |
O1—Cu1—N1—C8 | 173.7 (5) | C1—N1—C8—C13 | 136.6 (7) |
O1i—Cu1—N1—C8 | −88.4 (5) | Cu1—N1—C8—C13 | −80.8 (7) |
N2i—Cu1—N1—C8 | 3.0 (5) | N1—C8—C9—C10 | −175.2 (8) |
N2—Cu1—N1—C8 | 83.8 (5) | C13—C8—C9—C10 | −1.4 (12) |
N1i—Cu1—N1—C8 | −137.1 (5) | C8—C9—C10—C11 | 3.1 (15) |
O1—Cu1—N2—C22 | 7.0 (6) | C9—C10—C11—C12 | −2.7 (16) |
O1i—Cu1—N2—C22 | −136.8 (10) | C10—C11—C12—C13 | 0.6 (15) |
N2i—Cu1—N2—C22 | 179.5 (8) | C10—C11—C12—C17 | 177.6 (10) |
N1i—Cu1—N2—C22 | −79.0 (6) | C11—C12—C13—C14 | 178.9 (8) |
N1—Cu1—N2—C22 | 89.1 (6) | C17—C12—C13—C14 | 1.8 (12) |
O1—Cu1—N2—C18 | −172.5 (5) | C11—C12—C13—C8 | 1.0 (12) |
O1i—Cu1—N2—C18 | 43.7 (14) | C17—C12—C13—C8 | −176.1 (8) |
N2i—Cu1—N2—C18 | −0.1 (4) | C9—C8—C13—C14 | −178.4 (8) |
N1i—Cu1—N2—C18 | 101.4 (5) | N1—C8—C13—C14 | −4.5 (11) |
N1—Cu1—N2—C18 | −90.5 (5) | C9—C8—C13—C12 | −0.6 (11) |
O1i—Cu1—O1—C3 | −35.9 (5) | N1—C8—C13—C12 | 173.4 (7) |
N2i—Cu1—O1—C3 | 107.5 (12) | C12—C13—C14—C15 | −1.5 (13) |
N2—Cu1—O1—C3 | 150.6 (6) | C8—C13—C14—C15 | 176.3 (8) |
N1i—Cu1—O1—C3 | −117.2 (6) | C13—C14—C15—C16 | 1.5 (15) |
N1—Cu1—O1—C3 | 49.0 (5) | C14—C15—C16—C17 | −1.7 (17) |
C8—N1—C1—C2 | 172.1 (7) | C15—C16—C17—C12 | 2.0 (17) |
Cu1—N1—C1—C2 | 28.7 (9) | C11—C12—C17—C16 | −179.1 (10) |
N1—C1—C2—C7 | 177.3 (7) | C13—C12—C17—C16 | −2.1 (15) |
N1—C1—C2—C3 | −3.7 (11) | C22—N2—C18—C19 | 0.2 (11) |
Cu1—O1—C3—C2 | −41.1 (9) | Cu1—N2—C18—C19 | 179.8 (6) |
Cu1—O1—C3—C4 | 141.3 (5) | C22—N2—C18—C18i | −179.4 (7) |
C7—C2—C3—O1 | −177.1 (6) | Cu1—N2—C18—C18i | 0.2 (10) |
C1—C2—C3—O1 | 4.0 (10) | N2—C18—C19—C20 | −0.1 (11) |
C7—C2—C3—C4 | 0.6 (9) | C18i—C18—C19—C20 | 179.5 (8) |
C1—C2—C3—C4 | −178.3 (6) | N2—C18—C19—C23 | 179.7 (7) |
O1—C3—C4—C5 | 177.7 (6) | C18i—C18—C19—C23 | −0.7 (13) |
C2—C3—C4—C5 | −0.1 (10) | C18—C19—C20—C21 | 0.1 (12) |
O1—C3—C4—Br1 | −3.7 (9) | C23—C19—C20—C21 | −179.6 (9) |
C2—C3—C4—Br1 | 178.5 (5) | C19—C20—C21—C22 | −0.3 (13) |
C3—C4—C5—C6 | −0.7 (11) | C18—N2—C22—C21 | −0.4 (11) |
Br1—C4—C5—C6 | −179.3 (5) | Cu1—N2—C22—C21 | −179.9 (6) |
C4—C5—C6—C7 | 1.0 (11) | C20—C21—C22—N2 | 0.4 (13) |
C4—C5—C6—Br2 | −178.9 (5) | C18—C19—C23—C23i | 1.3 (16) |
C5—C6—C7—C2 | −0.6 (12) | C20—C19—C23—C23i | −179.0 (10) |
Symmetry code: (i) −x+1, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Br1ii | 0.93 | 2.93 | 3.773 (13) | 152 |
Symmetry code: (ii) x+3/2, y+5/2, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C17H10Br2NO)2(C12H8N2)] |
Mr | 1051.90 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 298 |
a, b, c (Å) | 20.288 (2), 14.5052 (18), 15.227 (2) |
β (°) | 116.977 (2) |
V (Å3) | 3993.5 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.59 |
Crystal size (mm) | 0.38 × 0.19 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.274, 0.509 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10067, 3513, 1877 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.165, 0.97 |
No. of reflections | 3513 |
No. of parameters | 258 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.95, −0.73 |
Computer programs: SMART (Bruker 2001), SAINT (Bruker 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···Br1i | 0.9297 | 2.9259 | 3.773 (13) | 152.21 |
Symmetry code: (i) x+3/2, y+5/2, z. |
Schiff bases play an important role in inorganic chemistry as they easily form stable complexes with most transition metal ions (Mostafa & Haifaa, 2007, Musie et al., 2003, Patel et al., 2006). We report herein the synthesis and crystal structure of (I), Fig 1, a mononuclear Cu(II) complex of the new Schiff base ligand 2,4-dibromo-6-((naphthalen-1-ylimino)methyl)phenolate and 1,10-phenanthroline. The copperII cation lies on a twofold axis and is coordinated by two N and two O atoms from the Schiff base and two N atoms from 1,10-phenanthroline, in a slightly distorted octahedral geometry.
In the crystal weak, non-classical C—H···Br hydrogen bonds link the molecules in rows along c, Fig 2.