Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026773/bh2106sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026773/bh2106Isup2.hkl |
CCDC reference: 654709
To a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C14H12N2.0.5 H2O, 0.22 g, 1 mmol) and sodium benzoate (0.17 g, 1 mmol) in ethanol/water (20 ml) was added a solution of CuCl2.2H2O (0.18 g, 1 mmol) in distilled water (10 ml). The resulting solution was refluxed for 1 h and then a pale green precipitate was filtered. Blue single crystals of (I) were obtained by slow evaporation of the filtrate after 1 d.
H atoms were positioned geometrically and treated as riding, with C—H distances in the range 0.95–0.99 Å and with Uiso(H) = 1.2Ueq(C).
Copper(II) complexes of 1,10-phenanthroline and its derivatives have attracted much attention because of their peculiar features (Paulovicova et al., 2001; Pallenberg et al., 1995). Recently, we obtained the title mononuclear copper(II) complex, (I), by reaction of copper dichloride, sodium benzoate and 2,9-dimethyl-1,10-phenanthroline (dmphen) in an ethanol/water mixture, and its crystal structure is reported here.
The CuII ion in (I) has a distorted square-pyramidal geometry, with the apical position occupied by one Cl- anion (Fig. 1). Two N atoms of one dmphen molecule and two O atoms of one benzoate anion form the basal plane.
Molecules in the crystal are arranged in chains formed by π–π stacking of the dmphen molecules (Fig. 2). These intermolecular interactions occur between rings C8···C11/N1/C13 and C2···C5/C14/N2 within the staggered conformation. The distance between the ring centroids X(1 A) and X(1B) and the perpendicular distance from X(1 A) to X(1B) rings (symmetry code for symmetry related molecules: 1 + x, 1/2 + y, -z) are 3.978 (5) and 3.614 (5) Å, respectively. The dihedral angle between these planes is 2.8 (5)°.
For related literature, see: Pallenberg et al. (1995); Tian & Long (2000); Paulovicova et al. (2001); Lemoine et al. (2003).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.
[Cu(C7H5O2)Cl(C14H12N2)] | F(000) = 876 |
Mr = 428.36 | Dx = 1.514 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4230 reflections |
a = 8.0991 (8) Å | θ = 2.6–22.1° |
b = 15.9385 (15) Å | µ = 1.32 mm−1 |
c = 15.0440 (14) Å | T = 291 K |
β = 104.610 (1)° | Block, blue |
V = 1879.2 (3) Å3 | 0.36 × 0.27 × 0.24 mm |
Z = 4 |
SMART CCD area-detector diffractometer | 3499 independent reflections |
Radiation source: fine-focus sealed tube | 2627 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 25.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→9 |
Tmin = 0.634, Tmax = 0.727 | k = −19→19 |
14114 measured reflections | l = −18→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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0601P)2 + 0.8256P] where P = (Fo2 + 2Fc2)/3 |
3499 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
[Cu(C7H5O2)Cl(C14H12N2)] | V = 1879.2 (3) Å3 |
Mr = 428.36 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.0991 (8) Å | µ = 1.32 mm−1 |
b = 15.9385 (15) Å | T = 291 K |
c = 15.0440 (14) Å | 0.36 × 0.27 × 0.24 mm |
β = 104.610 (1)° |
SMART CCD area-detector diffractometer | 3499 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2627 reflections with I > 2σ(I) |
Tmin = 0.634, Tmax = 0.727 | Rint = 0.021 |
14114 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.55 e Å−3 |
3499 reflections | Δρmin = −0.28 e Å−3 |
246 parameters |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.25490 (5) | 0.18713 (2) | 0.62658 (3) | 0.06726 (17) | |
Cl1 | 0.51574 (12) | 0.20729 (7) | 0.72554 (7) | 0.0892 (3) | |
O1 | 0.0325 (3) | 0.23262 (14) | 0.6526 (2) | 0.0883 (7) | |
O2 | 0.1888 (4) | 0.30772 (16) | 0.5907 (2) | 0.1047 (9) | |
N1 | 0.2118 (3) | 0.06795 (16) | 0.6532 (2) | 0.0692 (7) | |
N2 | 0.2893 (3) | 0.13257 (18) | 0.50468 (17) | 0.0654 (7) | |
C1 | 0.3686 (5) | 0.2577 (3) | 0.4339 (3) | 0.0989 (13) | |
H1A | 0.2619 | 0.2872 | 0.4191 | 0.148* | |
H1B | 0.4306 | 0.2704 | 0.3890 | 0.148* | |
H1C | 0.4344 | 0.2747 | 0.4936 | 0.148* | |
C2 | 0.3361 (4) | 0.1660 (3) | 0.4340 (2) | 0.0798 (10) | |
C3 | 0.3579 (5) | 0.1140 (4) | 0.3609 (3) | 0.1068 (15) | |
H3 | 0.3925 | 0.1375 | 0.3120 | 0.128* | |
C4 | 0.3290 (5) | 0.0311 (4) | 0.3621 (3) | 0.1126 (17) | |
H4 | 0.3411 | −0.0019 | 0.3132 | 0.135* | |
C5 | 0.2808 (4) | −0.0064 (3) | 0.4361 (3) | 0.0914 (12) | |
C6 | 0.2490 (6) | −0.0936 (3) | 0.4431 (4) | 0.1109 (17) | |
H6 | 0.2599 | −0.1295 | 0.3961 | 0.133* | |
C7 | 0.2039 (6) | −0.1248 (3) | 0.5157 (4) | 0.1129 (17) | |
H7 | 0.1829 | −0.1821 | 0.5178 | 0.135* | |
C8 | 0.1869 (4) | −0.0736 (2) | 0.5896 (3) | 0.0878 (12) | |
C9 | 0.1446 (5) | −0.1015 (3) | 0.6678 (4) | 0.1085 (15) | |
H9 | 0.1211 | −0.1580 | 0.6738 | 0.130* | |
C10 | 0.1370 (6) | −0.0480 (3) | 0.7348 (4) | 0.1115 (15) | |
H10 | 0.1088 | −0.0679 | 0.7872 | 0.134* | |
C11 | 0.1711 (5) | 0.0386 (2) | 0.7277 (3) | 0.0916 (11) | |
C12 | 0.1657 (7) | 0.0984 (3) | 0.8021 (3) | 0.1284 (19) | |
H12A | 0.2645 | 0.1340 | 0.8135 | 0.193* | |
H12B | 0.1647 | 0.0680 | 0.8570 | 0.193* | |
H12C | 0.0645 | 0.1321 | 0.7842 | 0.193* | |
C13 | 0.2195 (4) | 0.0140 (2) | 0.5848 (3) | 0.0703 (9) | |
C14 | 0.2637 (4) | 0.0475 (2) | 0.5068 (2) | 0.0702 (9) | |
C15 | 0.0574 (4) | 0.30065 (18) | 0.6177 (2) | 0.0618 (7) | |
C16 | −0.0696 (4) | 0.36993 (19) | 0.60953 (19) | 0.0636 (7) | |
C17 | −0.2333 (4) | 0.3520 (3) | 0.6138 (2) | 0.0802 (10) | |
H17 | −0.2644 | 0.2972 | 0.6234 | 0.096* | |
C18 | −0.3518 (5) | 0.4165 (3) | 0.6036 (3) | 0.1022 (13) | |
H18 | −0.4641 | 0.4044 | 0.6037 | 0.123* | |
C19 | −0.3057 (7) | 0.4971 (3) | 0.5935 (3) | 0.1080 (14) | |
H19 | −0.3858 | 0.5399 | 0.5882 | 0.130* | |
C20 | −0.1434 (7) | 0.5157 (3) | 0.5911 (3) | 0.1134 (15) | |
H20 | −0.1113 | 0.5712 | 0.5859 | 0.136* | |
C21 | −0.0254 (5) | 0.4515 (2) | 0.5965 (3) | 0.0924 (11) | |
H21 | 0.0840 | 0.4637 | 0.5912 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0660 (3) | 0.0575 (2) | 0.0816 (3) | 0.00553 (17) | 0.0248 (2) | 0.00678 (18) |
Cl1 | 0.0797 (6) | 0.0941 (7) | 0.0833 (6) | −0.0101 (5) | 0.0008 (4) | −0.0077 (5) |
O1 | 0.0784 (15) | 0.0559 (14) | 0.136 (2) | 0.0059 (11) | 0.0374 (15) | 0.0078 (14) |
O2 | 0.104 (2) | 0.0773 (17) | 0.156 (3) | 0.0294 (14) | 0.0753 (19) | 0.0437 (16) |
N1 | 0.0591 (14) | 0.0613 (15) | 0.0919 (19) | 0.0120 (12) | 0.0276 (13) | 0.0080 (14) |
N2 | 0.0464 (13) | 0.0868 (19) | 0.0587 (15) | 0.0011 (12) | 0.0053 (11) | −0.0053 (13) |
C1 | 0.088 (3) | 0.136 (4) | 0.073 (2) | −0.009 (3) | 0.0217 (19) | 0.023 (2) |
C2 | 0.0550 (18) | 0.120 (3) | 0.0585 (19) | −0.0011 (18) | 0.0035 (15) | −0.005 (2) |
C3 | 0.070 (2) | 0.185 (5) | 0.061 (2) | 0.000 (3) | 0.0065 (17) | −0.010 (3) |
C4 | 0.075 (3) | 0.166 (5) | 0.083 (3) | 0.019 (3) | −0.005 (2) | −0.051 (3) |
C5 | 0.056 (2) | 0.114 (3) | 0.088 (3) | 0.0143 (19) | −0.0118 (18) | −0.034 (2) |
C6 | 0.082 (3) | 0.095 (3) | 0.129 (4) | 0.019 (2) | −0.022 (3) | −0.055 (3) |
C7 | 0.078 (3) | 0.077 (3) | 0.154 (5) | 0.007 (2) | −0.027 (3) | −0.029 (3) |
C8 | 0.0470 (17) | 0.070 (2) | 0.130 (3) | 0.0055 (15) | −0.008 (2) | −0.008 (2) |
C9 | 0.068 (2) | 0.082 (3) | 0.166 (5) | −0.002 (2) | 0.012 (3) | 0.030 (3) |
C10 | 0.096 (3) | 0.096 (3) | 0.154 (4) | 0.013 (3) | 0.054 (3) | 0.046 (3) |
C11 | 0.086 (2) | 0.080 (2) | 0.121 (3) | 0.018 (2) | 0.049 (2) | 0.028 (2) |
C12 | 0.176 (5) | 0.116 (4) | 0.123 (4) | 0.040 (3) | 0.095 (4) | 0.039 (3) |
C13 | 0.0426 (15) | 0.065 (2) | 0.095 (2) | 0.0062 (13) | 0.0038 (15) | −0.0020 (18) |
C14 | 0.0411 (15) | 0.081 (2) | 0.077 (2) | 0.0106 (14) | −0.0052 (14) | −0.0212 (18) |
C15 | 0.0630 (18) | 0.0551 (18) | 0.0635 (18) | −0.0012 (13) | 0.0090 (14) | −0.0038 (14) |
C16 | 0.0710 (19) | 0.0636 (18) | 0.0524 (16) | 0.0075 (15) | 0.0087 (14) | −0.0029 (13) |
C17 | 0.071 (2) | 0.082 (2) | 0.087 (2) | 0.0052 (18) | 0.0190 (18) | −0.0189 (19) |
C18 | 0.080 (3) | 0.117 (4) | 0.112 (3) | 0.020 (2) | 0.027 (2) | −0.019 (3) |
C19 | 0.112 (4) | 0.102 (3) | 0.110 (3) | 0.046 (3) | 0.030 (3) | −0.001 (3) |
C20 | 0.123 (4) | 0.077 (3) | 0.145 (4) | 0.033 (3) | 0.042 (3) | 0.029 (3) |
C21 | 0.090 (3) | 0.071 (2) | 0.120 (3) | 0.0204 (19) | 0.035 (2) | 0.022 (2) |
Cu1—N1 | 1.990 (3) | C7—C8 | 1.414 (6) |
Cu1—O2 | 2.031 (2) | C7—H7 | 0.9300 |
Cu1—O1 | 2.069 (2) | C8—C9 | 1.379 (6) |
Cu1—N2 | 2.111 (3) | C8—C13 | 1.426 (5) |
Cu1—Cl1 | 2.2795 (10) | C9—C10 | 1.334 (7) |
Cu1—C15 | 2.396 (3) | C9—H9 | 0.9300 |
O1—C15 | 1.243 (4) | C10—C11 | 1.417 (6) |
O2—C15 | 1.236 (4) | C10—H10 | 0.9300 |
N1—C11 | 1.330 (5) | C11—C12 | 1.480 (6) |
N1—C13 | 1.356 (4) | C12—H12A | 0.9600 |
N2—C2 | 1.328 (4) | C12—H12B | 0.9600 |
N2—C14 | 1.374 (4) | C12—H12C | 0.9600 |
C1—C2 | 1.485 (5) | C13—C14 | 1.414 (5) |
C1—H1A | 0.9600 | C15—C16 | 1.493 (4) |
C1—H1B | 0.9600 | C16—C17 | 1.374 (5) |
C1—H1C | 0.9600 | C16—C21 | 1.376 (5) |
C2—C3 | 1.424 (6) | C17—C18 | 1.389 (5) |
C3—C4 | 1.342 (7) | C17—H17 | 0.9300 |
C3—H3 | 0.9300 | C18—C19 | 1.357 (6) |
C4—C5 | 1.402 (7) | C18—H18 | 0.9300 |
C4—H4 | 0.9300 | C19—C20 | 1.357 (6) |
C5—C14 | 1.401 (5) | C19—H19 | 0.9300 |
C5—C6 | 1.423 (6) | C20—C21 | 1.388 (5) |
C6—C7 | 1.333 (7) | C20—H20 | 0.9300 |
C6—H6 | 0.9300 | C21—H21 | 0.9300 |
N1—Cu1—O2 | 155.33 (11) | C9—C8—C13 | 116.6 (4) |
N1—Cu1—O1 | 95.23 (10) | C7—C8—C13 | 117.9 (5) |
O2—Cu1—O1 | 62.29 (10) | C10—C9—C8 | 120.5 (4) |
N1—Cu1—N2 | 81.37 (12) | C10—C9—H9 | 119.8 |
O2—Cu1—N2 | 104.05 (12) | C8—C9—H9 | 119.8 |
O1—Cu1—N2 | 128.40 (10) | C9—C10—C11 | 121.3 (5) |
N1—Cu1—Cl1 | 100.58 (8) | C9—C10—H10 | 119.4 |
O2—Cu1—Cl1 | 100.31 (11) | C11—C10—H10 | 119.4 |
O1—Cu1—Cl1 | 122.31 (8) | N1—C11—C10 | 120.0 (4) |
N2—Cu1—Cl1 | 108.78 (7) | N1—C11—C12 | 118.2 (4) |
N1—Cu1—C15 | 125.70 (10) | C10—C11—C12 | 121.8 (4) |
O2—Cu1—C15 | 31.05 (10) | C11—C12—H12A | 109.5 |
O1—Cu1—C15 | 31.25 (9) | C11—C12—H12B | 109.5 |
N2—Cu1—C15 | 119.69 (10) | H12A—C12—H12B | 109.5 |
Cl1—Cu1—C15 | 115.18 (8) | C11—C12—H12C | 109.5 |
C15—O1—Cu1 | 89.06 (19) | H12A—C12—H12C | 109.5 |
C15—O2—Cu1 | 91.0 (2) | H12B—C12—H12C | 109.5 |
C11—N1—C13 | 119.1 (3) | N1—C13—C14 | 117.4 (3) |
C11—N1—Cu1 | 126.7 (3) | N1—C13—C8 | 122.5 (4) |
C13—N1—Cu1 | 114.1 (2) | C14—C13—C8 | 120.1 (4) |
C2—N2—C14 | 119.4 (3) | N2—C14—C5 | 122.8 (4) |
C2—N2—Cu1 | 131.1 (3) | N2—C14—C13 | 117.6 (3) |
C14—N2—Cu1 | 109.4 (2) | C5—C14—C13 | 119.5 (4) |
C2—C1—H1A | 109.5 | O2—C15—O1 | 117.6 (3) |
C2—C1—H1B | 109.5 | O2—C15—C16 | 122.5 (3) |
H1A—C1—H1B | 109.5 | O1—C15—C16 | 119.9 (3) |
C2—C1—H1C | 109.5 | O2—C15—Cu1 | 57.96 (16) |
H1A—C1—H1C | 109.5 | O1—C15—Cu1 | 59.69 (16) |
H1B—C1—H1C | 109.5 | C16—C15—Cu1 | 178.1 (2) |
N2—C2—C3 | 120.0 (4) | C17—C16—C21 | 119.5 (3) |
N2—C2—C1 | 118.9 (3) | C17—C16—C15 | 119.7 (3) |
C3—C2—C1 | 121.1 (4) | C21—C16—C15 | 120.8 (3) |
C4—C3—C2 | 120.5 (4) | C16—C17—C18 | 119.2 (4) |
C4—C3—H3 | 119.8 | C16—C17—H17 | 120.4 |
C2—C3—H3 | 119.8 | C18—C17—H17 | 120.4 |
C3—C4—C5 | 121.0 (4) | C19—C18—C17 | 120.8 (4) |
C3—C4—H4 | 119.5 | C19—C18—H18 | 119.6 |
C5—C4—H4 | 119.5 | C17—C18—H18 | 119.6 |
C14—C5—C4 | 116.3 (4) | C20—C19—C18 | 120.3 (4) |
C14—C5—C6 | 119.2 (5) | C20—C19—H19 | 119.8 |
C4—C5—C6 | 124.5 (5) | C18—C19—H19 | 119.8 |
C7—C6—C5 | 121.2 (5) | C19—C20—C21 | 119.6 (4) |
C7—C6—H6 | 119.4 | C19—C20—H20 | 120.2 |
C5—C6—H6 | 119.4 | C21—C20—H20 | 120.2 |
C6—C7—C8 | 122.1 (5) | C16—C21—C20 | 120.3 (4) |
C6—C7—H7 | 119.0 | C16—C21—H21 | 119.8 |
C8—C7—H7 | 119.0 | C20—C21—H21 | 119.8 |
C9—C8—C7 | 125.4 (5) | ||
N1—Cu1—O1—C15 | −168.1 (2) | Cu1—N1—C11—C12 | −3.8 (5) |
O2—Cu1—O1—C15 | 1.2 (2) | C9—C10—C11—N1 | −0.1 (7) |
N2—Cu1—O1—C15 | −85.0 (2) | C9—C10—C11—C12 | −179.1 (5) |
Cl1—Cu1—O1—C15 | 85.9 (2) | C11—N1—C13—C14 | −179.8 (3) |
N1—Cu1—O2—C15 | 25.0 (5) | Cu1—N1—C13—C14 | 2.8 (3) |
O1—Cu1—O2—C15 | −1.2 (2) | C11—N1—C13—C8 | −0.5 (5) |
N2—Cu1—O2—C15 | 125.1 (2) | Cu1—N1—C13—C8 | −177.9 (2) |
Cl1—Cu1—O2—C15 | −122.4 (2) | C9—C8—C13—N1 | 0.7 (5) |
O2—Cu1—N1—C11 | −74.0 (4) | C7—C8—C13—N1 | −178.0 (3) |
O1—Cu1—N1—C11 | −50.8 (3) | C9—C8—C13—C14 | −180.0 (3) |
N2—Cu1—N1—C11 | −178.9 (3) | C7—C8—C13—C14 | 1.3 (4) |
Cl1—Cu1—N1—C11 | 73.4 (3) | C2—N2—C14—C5 | −1.6 (4) |
C15—Cu1—N1—C11 | −58.4 (3) | Cu1—N2—C14—C5 | −178.7 (2) |
O2—Cu1—N1—C13 | 103.2 (3) | C2—N2—C14—C13 | 177.9 (3) |
O1—Cu1—N1—C13 | 126.3 (2) | Cu1—N2—C14—C13 | 0.8 (3) |
N2—Cu1—N1—C13 | −1.8 (2) | C4—C5—C14—N2 | 1.0 (4) |
Cl1—Cu1—N1—C13 | −109.4 (2) | C6—C5—C14—N2 | −178.9 (3) |
C15—Cu1—N1—C13 | 118.8 (2) | C4—C5—C14—C13 | −178.5 (3) |
N1—Cu1—N2—C2 | −176.2 (3) | C6—C5—C14—C13 | 1.6 (5) |
O2—Cu1—N2—C2 | 28.4 (3) | N1—C13—C14—N2 | −2.4 (4) |
O1—Cu1—N2—C2 | 94.0 (3) | C8—C13—C14—N2 | 178.3 (3) |
Cl1—Cu1—N2—C2 | −77.9 (3) | N1—C13—C14—C5 | 177.2 (3) |
C15—Cu1—N2—C2 | 57.5 (3) | C8—C13—C14—C5 | −2.2 (4) |
N1—Cu1—N2—C14 | 0.52 (18) | Cu1—O2—C15—O1 | 2.0 (3) |
O2—Cu1—N2—C14 | −154.91 (19) | Cu1—O2—C15—C16 | −177.8 (3) |
O1—Cu1—N2—C14 | −89.3 (2) | Cu1—O1—C15—O2 | −2.0 (3) |
Cl1—Cu1—N2—C14 | 98.83 (17) | Cu1—O1—C15—C16 | 177.8 (2) |
C15—Cu1—N2—C14 | −125.84 (18) | N1—Cu1—C15—O2 | −167.4 (2) |
C14—N2—C2—C3 | 0.5 (4) | O1—Cu1—C15—O2 | 177.9 (4) |
Cu1—N2—C2—C3 | 177.0 (2) | N2—Cu1—C15—O2 | −66.1 (3) |
C14—N2—C2—C1 | −178.1 (3) | Cl1—Cu1—C15—O2 | 66.6 (3) |
Cu1—N2—C2—C1 | −1.7 (4) | N1—Cu1—C15—O1 | 14.6 (2) |
N2—C2—C3—C4 | 1.0 (6) | O2—Cu1—C15—O1 | −177.9 (4) |
C1—C2—C3—C4 | 179.6 (4) | N2—Cu1—C15—O1 | 116.0 (2) |
C2—C3—C4—C5 | −1.6 (6) | Cl1—Cu1—C15—O1 | −111.34 (19) |
C3—C4—C5—C14 | 0.6 (6) | O2—C15—C16—C17 | 160.2 (3) |
C3—C4—C5—C6 | −179.5 (4) | O1—C15—C16—C17 | −19.6 (4) |
C14—C5—C6—C7 | −0.2 (6) | O2—C15—C16—C21 | −18.9 (5) |
C4—C5—C6—C7 | 179.9 (4) | O1—C15—C16—C21 | 161.3 (3) |
C5—C6—C7—C8 | −0.7 (7) | C21—C16—C17—C18 | 0.9 (5) |
C6—C7—C8—C9 | −178.5 (4) | C15—C16—C17—C18 | −178.3 (3) |
C6—C7—C8—C13 | 0.1 (6) | C16—C17—C18—C19 | −2.8 (6) |
C7—C8—C9—C10 | 178.0 (4) | C17—C18—C19—C20 | 1.5 (7) |
C13—C8—C9—C10 | −0.6 (6) | C18—C19—C20—C21 | 1.8 (8) |
C8—C9—C10—C11 | 0.3 (7) | C17—C16—C21—C20 | 2.4 (6) |
C13—N1—C11—C10 | 0.2 (5) | C15—C16—C21—C20 | −178.5 (4) |
Cu1—N1—C11—C10 | 177.2 (3) | C19—C20—C21—C16 | −3.8 (7) |
C13—N1—C11—C12 | 179.2 (3) |
Experimental details
Crystal data | |
Chemical formula | [Cu(C7H5O2)Cl(C14H12N2)] |
Mr | 428.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 291 |
a, b, c (Å) | 8.0991 (8), 15.9385 (15), 15.0440 (14) |
β (°) | 104.610 (1) |
V (Å3) | 1879.2 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.32 |
Crystal size (mm) | 0.36 × 0.27 × 0.24 |
Data collection | |
Diffractometer | SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.634, 0.727 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14114, 3499, 2627 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.118, 1.03 |
No. of reflections | 3499 |
No. of parameters | 246 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.55, −0.28 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
Copper(II) complexes of 1,10-phenanthroline and its derivatives have attracted much attention because of their peculiar features (Paulovicova et al., 2001; Pallenberg et al., 1995). Recently, we obtained the title mononuclear copper(II) complex, (I), by reaction of copper dichloride, sodium benzoate and 2,9-dimethyl-1,10-phenanthroline (dmphen) in an ethanol/water mixture, and its crystal structure is reported here.
The CuII ion in (I) has a distorted square-pyramidal geometry, with the apical position occupied by one Cl- anion (Fig. 1). Two N atoms of one dmphen molecule and two O atoms of one benzoate anion form the basal plane.
Molecules in the crystal are arranged in chains formed by π–π stacking of the dmphen molecules (Fig. 2). These intermolecular interactions occur between rings C8···C11/N1/C13 and C2···C5/C14/N2 within the staggered conformation. The distance between the ring centroids X(1 A) and X(1B) and the perpendicular distance from X(1 A) to X(1B) rings (symmetry code for symmetry related molecules: 1 + x, 1/2 + y, -z) are 3.978 (5) and 3.614 (5) Å, respectively. The dihedral angle between these planes is 2.8 (5)°.