Literature DB >> 21836872

{N,N'-Bis[1-(pyridin-2-yl)ethyl-idene]-propane-1,3-diamine}-bromidocopper(II) tetra-fluoridoborate.

Abstract

In the title compound, [CuBr(C(17)H(20)N(4))]BF(4), the Cu(II) ion is five-coordinated by the four N atoms of the tetra-dentate Schiff base ligand and by one bromide ion, thereby forming a square-pyramidal CuN(4)Br coordination geometry. The dihedral angle between the pyridine rings of the Schiff base is 54.39 (18)°. In the crystal, the components are linked by C-H⋯F inter-actions.

Entities: Chemical Disease Gene Species

Year: 2011 PMID： 21836872 PMCID： PMC3151825 DOI： 10.1107/S1600536811022513

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For a related structure and background references, see: Liu (2011 ▶).

Experimental

Crystal data

[CuBr(C17H20N4)]BF4 M = 510.63 Triclinic, a = 8.2508 (17) Å b = 8.9511 (18) Å c = 13.158 (3) Å α = 92.391 (2)° β = 94.847 (2)° γ = 96.422 (2)° V = 960.9 (3) Å3 Z = 2 Mo Kα radiation μ = 3.26 mm−1 T = 298 K 0.27 × 0.27 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.473, T max = 0.521 5958 measured reflections 3683 independent reflections 2723 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.087 S = 1.05 3683 reflections 255 parameters H-atom parameters constrained Δρmax = 0.39 e Å−3 Δρmin = −0.46 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022513/hb5900sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022513/hb5900Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CuBr(C₁₇H₂₀N₄)]BF₄	Z = 2
M_r = 510.63	F(000) = 510
Triclinic, P1	D_x = 1.765 Mg m⁻³
a = 8.2508 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9511 (18) Å	Cell parameters from 1747 reflections
c = 13.158 (3) Å	θ = 2.5–25.3°
α = 92.391 (2)°	µ = 3.26 mm⁻¹
β = 94.847 (2)°	T = 298 K
γ = 96.422 (2)°	Block, blue
V = 960.9 (3) Å³	0.27 × 0.27 × 0.23 mm

Bruker APEXII CCD diffractometer	3683 independent reflections
Radiation source: fine-focus sealed tube	2723 reflections with I > 2σ(I)
graphite	R_int = 0.026
ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→10
T_min = 0.473, T_max = 0.521	k = −11→10
5958 measured reflections	l = −16→11

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0353P)² + 0.1409P] where P = (F_o² + 2F_c²)/3
3683 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.46 e Å⁻³

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	U_iso*/U_eq
Cu1	0.90467 (5)	0.78988 (5)	0.74936 (3)	0.03382 (14)
Br1	1.14320 (5)	0.95979 (5)	0.69040 (3)	0.04830 (14)
F1	0.5630 (4)	0.4076 (3)	0.2862 (2)	0.0787 (8)
F2	0.4093 (3)	0.5940 (3)	0.2543 (2)	0.0754 (8)
F3	0.6555 (3)	0.5941 (3)	0.1938 (2)	0.0870 (9)
F4	0.4467 (4)	0.4290 (3)	0.1279 (2)	0.0792 (8)
N1	0.9085 (3)	0.5870 (3)	0.6691 (2)	0.0318 (7)
N2	0.7458 (4)	0.8146 (3)	0.6317 (2)	0.0370 (7)
N3	0.7643 (3)	0.8783 (3)	0.8484 (2)	0.0339 (7)
N4	1.0231 (3)	0.7455 (3)	0.8815 (2)	0.0343 (7)
B1	0.5174 (6)	0.5077 (5)	0.2150 (4)	0.0410 (11)
C1	0.8099 (4)	0.5758 (4)	0.5809 (3)	0.0333 (8)
C2	0.7912 (5)	0.4481 (4)	0.5165 (3)	0.0410 (10)
H2	0.7238	0.4432	0.4558	0.049*
C3	0.8740 (5)	0.3273 (4)	0.5435 (3)	0.0490 (11)
H3	0.8628	0.2403	0.5011	0.059*
C4	0.9726 (5)	0.3373 (4)	0.6333 (3)	0.0463 (10)
H4	1.0284	0.2570	0.6530	0.056*
C5	0.9879 (5)	0.4694 (4)	0.6942 (3)	0.0388 (9)
H5	1.0558	0.4764	0.7548	0.047*
C6	0.7252 (4)	0.7110 (4)	0.5613 (3)	0.0338 (8)
C7	0.6216 (5)	0.7181 (5)	0.4626 (3)	0.0549 (12)
H7A	0.5098	0.7227	0.4763	0.082*
H7B	0.6287	0.6299	0.4198	0.082*
H7C	0.6602	0.8062	0.4285	0.082*
C8	0.6550 (5)	0.9469 (4)	0.6228 (3)	0.0506 (11)
H8A	0.5399	0.9130	0.6050	0.061*
H8B	0.6943	1.0060	0.5678	0.061*
C9	0.6728 (5)	1.0446 (4)	0.7192 (3)	0.0496 (11)
H9A	0.6033	1.1245	0.7103	0.060*
H9B	0.7852	1.0911	0.7308	0.060*
C10	0.6290 (5)	0.9614 (5)	0.8124 (3)	0.0478 (11)
H10A	0.6076	1.0324	0.8660	0.057*
H10B	0.5305	0.8919	0.7956	0.057*
C11	0.7903 (4)	0.8446 (4)	0.9409 (3)	0.0339 (8)
C12	0.6860 (5)	0.8754 (5)	1.0249 (3)	0.0546 (12)
H12A	0.7435	0.9522	1.0718	0.082*
H12B	0.6614	0.7850	1.0601	0.082*
H12C	0.5860	0.9089	0.9966	0.082*
C13	0.9414 (4)	0.7715 (4)	0.9639 (3)	0.0316 (8)
C14	0.9996 (5)	0.7370 (5)	1.0603 (3)	0.0447 (10)
H14	0.9410	0.7538	1.1163	0.054*
C15	1.1478 (5)	0.6765 (5)	1.0722 (3)	0.0492 (11)
H15	1.1893	0.6518	1.1364	0.059*
C16	1.2322 (5)	0.6535 (4)	0.9889 (3)	0.0434 (10)
H16	1.3313	0.6130	0.9960	0.052*
C17	1.1684 (4)	0.6912 (4)	0.8944 (3)	0.0403 (9)
H17	1.2275	0.6788	0.8381	0.048*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0384 (3)	0.0369 (3)	0.0276 (3)	0.0138 (2)	−0.00162 (19)	0.00188 (19)
Br1	0.0507 (3)	0.0410 (3)	0.0523 (3)	−0.00041 (19)	0.0050 (2)	0.00788 (19)
F1	0.103 (2)	0.0687 (19)	0.0661 (19)	0.0260 (16)	−0.0107 (16)	0.0165 (15)
F2	0.0599 (16)	0.101 (2)	0.0701 (18)	0.0396 (16)	0.0013 (14)	−0.0089 (16)
F3	0.0684 (19)	0.080 (2)	0.112 (3)	−0.0095 (16)	0.0233 (17)	0.0126 (18)
F4	0.096 (2)	0.0772 (19)	0.0576 (18)	0.0063 (16)	−0.0192 (15)	−0.0198 (15)
N1	0.0362 (17)	0.0312 (17)	0.0286 (17)	0.0035 (13)	0.0064 (13)	0.0045 (13)
N2	0.0417 (19)	0.0374 (19)	0.0320 (18)	0.0093 (15)	−0.0039 (14)	0.0064 (15)
N3	0.0322 (17)	0.0351 (17)	0.0354 (18)	0.0110 (13)	0.0012 (14)	−0.0001 (14)
N4	0.0341 (17)	0.0398 (18)	0.0299 (17)	0.0095 (14)	0.0001 (14)	0.0019 (14)
B1	0.041 (3)	0.043 (3)	0.038 (3)	0.010 (2)	−0.003 (2)	−0.003 (2)
C1	0.033 (2)	0.035 (2)	0.031 (2)	−0.0037 (16)	0.0076 (16)	0.0049 (17)
C2	0.039 (2)	0.043 (2)	0.039 (2)	−0.0075 (18)	0.0090 (18)	−0.0057 (19)
C3	0.058 (3)	0.034 (2)	0.055 (3)	−0.009 (2)	0.026 (2)	−0.011 (2)
C4	0.056 (3)	0.030 (2)	0.058 (3)	0.0101 (19)	0.024 (2)	0.008 (2)
C5	0.046 (2)	0.038 (2)	0.035 (2)	0.0116 (18)	0.0108 (18)	0.0052 (18)
C6	0.0279 (19)	0.045 (2)	0.028 (2)	−0.0011 (16)	0.0007 (15)	0.0060 (18)
C7	0.054 (3)	0.065 (3)	0.042 (3)	0.004 (2)	−0.014 (2)	0.001 (2)
C8	0.061 (3)	0.045 (3)	0.047 (3)	0.020 (2)	−0.008 (2)	0.009 (2)
C9	0.058 (3)	0.040 (2)	0.054 (3)	0.025 (2)	−0.002 (2)	0.008 (2)
C10	0.042 (2)	0.049 (3)	0.056 (3)	0.024 (2)	0.003 (2)	0.003 (2)
C11	0.036 (2)	0.033 (2)	0.034 (2)	0.0071 (16)	0.0058 (17)	0.0003 (17)
C12	0.053 (3)	0.071 (3)	0.045 (3)	0.023 (2)	0.015 (2)	0.003 (2)
C13	0.0322 (19)	0.032 (2)	0.030 (2)	0.0042 (16)	−0.0006 (16)	−0.0007 (16)
C14	0.048 (2)	0.058 (3)	0.030 (2)	0.010 (2)	0.0038 (18)	0.0015 (19)
C15	0.056 (3)	0.058 (3)	0.034 (2)	0.014 (2)	−0.010 (2)	0.010 (2)
C16	0.039 (2)	0.052 (3)	0.040 (2)	0.0129 (19)	−0.0053 (19)	0.0042 (19)
C17	0.037 (2)	0.047 (2)	0.039 (2)	0.0144 (18)	0.0048 (18)	0.0019 (18)

Cu1—N2	1.978 (3)	C6—C7	1.501 (5)
Cu1—N4	1.998 (3)	C7—H7A	0.9600
Cu1—N3	2.010 (3)	C7—H7B	0.9600
Cu1—N1	2.067 (3)	C7—H7C	0.9600
Cu1—Br1	2.5447 (7)	C8—C9	1.498 (6)
F1—B1	1.381 (5)	C8—H8A	0.9700
F2—B1	1.363 (5)	C8—H8B	0.9700
F3—B1	1.360 (5)	C9—C10	1.511 (5)
F4—B1	1.370 (5)	C9—H9A	0.9700
N1—C5	1.339 (4)	C9—H9B	0.9700
N1—C1	1.354 (4)	C10—H10A	0.9700
N2—C6	1.270 (4)	C10—H10B	0.9700
N2—C8	1.474 (4)	C11—C13	1.486 (5)
N3—C11	1.272 (4)	C11—C12	1.492 (5)
N3—C10	1.467 (4)	C12—H12A	0.9600
N4—C17	1.343 (4)	C12—H12B	0.9600
N4—C13	1.349 (4)	C12—H12C	0.9600
C1—C2	1.381 (5)	C13—C14	1.378 (5)
C1—C6	1.485 (5)	C14—C15	1.392 (5)
C2—C3	1.385 (5)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.367 (5)
C3—C4	1.371 (6)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.380 (5)
C4—C5	1.388 (5)	C16—H16	0.9300
C4—H4	0.9300	C17—H17	0.9300
C5—H5	0.9300

N2—Cu1—N4	167.79 (12)	C6—C7—H7B	109.5
N2—Cu1—N3	92.15 (12)	H7A—C7—H7B	109.5
N4—Cu1—N3	79.82 (12)	C6—C7—H7C	109.5
N2—Cu1—N1	80.08 (12)	H7A—C7—H7C	109.5
N4—Cu1—N1	99.56 (12)	H7B—C7—H7C	109.5
N3—Cu1—N1	137.46 (11)	N2—C8—C9	112.8 (3)
N2—Cu1—Br1	96.74 (9)	N2—C8—H8A	109.0
N4—Cu1—Br1	95.17 (9)	C9—C8—H8A	109.0
N3—Cu1—Br1	118.16 (9)	N2—C8—H8B	109.0
N1—Cu1—Br1	104.32 (8)	C9—C8—H8B	109.0
C5—N1—C1	118.4 (3)	H8A—C8—H8B	107.8
C5—N1—Cu1	129.4 (2)	C8—C9—C10	113.9 (4)
C1—N1—Cu1	112.2 (2)	C8—C9—H9A	108.8
C6—N2—C8	120.0 (3)	C10—C9—H9A	108.8
C6—N2—Cu1	117.1 (2)	C8—C9—H9B	108.8
C8—N2—Cu1	122.9 (3)	C10—C9—H9B	108.8
C11—N3—C10	123.0 (3)	H9A—C9—H9B	107.7
C11—N3—Cu1	115.8 (2)	N3—C10—C9	109.7 (3)
C10—N3—Cu1	120.8 (2)	N3—C10—H10A	109.7
C17—N4—C13	119.2 (3)	C9—C10—H10A	109.7
C17—N4—Cu1	126.9 (2)	N3—C10—H10B	109.7
C13—N4—Cu1	113.8 (2)	C9—C10—H10B	109.7
F3—B1—F2	110.9 (4)	H10A—C10—H10B	108.2
F3—B1—F4	109.5 (4)	N3—C11—C13	114.8 (3)
F2—B1—F4	110.2 (4)	N3—C11—C12	125.8 (3)
F3—B1—F1	107.5 (3)	C13—C11—C12	119.4 (3)
F2—B1—F1	109.3 (4)	C11—C12—H12A	109.5
F4—B1—F1	109.3 (4)	C11—C12—H12B	109.5
N1—C1—C2	121.8 (3)	H12A—C12—H12B	109.5
N1—C1—C6	114.1 (3)	C11—C12—H12C	109.5
C2—C1—C6	124.1 (3)	H12A—C12—H12C	109.5
C1—C2—C3	119.1 (4)	H12B—C12—H12C	109.5
C1—C2—H2	120.4	N4—C13—C14	121.6 (3)
C3—C2—H2	120.4	N4—C13—C11	114.1 (3)
C4—C3—C2	119.3 (4)	C14—C13—C11	124.3 (3)
C4—C3—H3	120.4	C13—C14—C15	118.5 (4)
C2—C3—H3	120.4	C13—C14—H14	120.7
C3—C4—C5	118.9 (4)	C15—C14—H14	120.7
C3—C4—H4	120.6	C16—C15—C14	119.7 (4)
C5—C4—H4	120.6	C16—C15—H15	120.1
N1—C5—C4	122.5 (4)	C14—C15—H15	120.1
N1—C5—H5	118.8	C15—C16—C17	119.1 (4)
C4—C5—H5	118.8	C15—C16—H16	120.4
N2—C6—C1	116.3 (3)	C17—C16—H16	120.4
N2—C6—C7	124.1 (4)	N4—C17—C16	121.7 (3)
C1—C6—C7	119.6 (3)	N4—C17—H17	119.2
C6—C7—H7A	109.5	C16—C17—H17	119.2

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F1	0.93	2.49	3.413 (5)	173
C12—H12B···F3ⁱ	0.96	2.50	3.430 (5)	162
C15—H15···F2ⁱⁱ	0.93	2.40	3.252 (5)	152

Table 1

Selected bond lengths (Å)

Cu1—N2	1.978 (3)
Cu1—N4	1.998 (3)
Cu1—N3	2.010 (3)
Cu1—N1	2.067 (3)
Cu1—Br1	2.5447 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯F1	0.93	2.49	3.413 (5)	173
C12—H12B⋯F3ⁱ	0.96	2.50	3.430 (5)	162
C15—H15⋯F2ⁱⁱ	0.93	2.40	3.252 (5)	152

Symmetry codes: (i) ; (ii) .

2 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. {N,N'-Bis[1-(pyridin-2-yl)ethyl-idene]-propane-1,3-diamine}-(thio-cyanato-κN)copper(II) tetra-fluoridoborate.

Authors: Li-Jun Liu
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-06-11

2 in total