Bis{μ-4,4′,6,6′-tetra­bromo-2,2′-[o-phenyl­enebis(nitrilo­methyl­idyne)]­diphenol­ato}­bis­[(dimethyl­formamide)cadmium(II)]

Shi, S.; Song, X.; Hu, Z.; Yu, X.

doi:10.1107/S1600536807059612

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m36

https://doi.org/10.1107/S1600536807059612

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Bis{μ-4,4′,6,6′-tetrabromo-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato}bis[(dimethylformamide)cadmium(II)]

Shaomin Shi,^a,^b Xuegang Song,^b Zongqiu Hu ^b ^* and Xieqing Yu ^c

^aHubei Key Laboratory of Bioanalytical Techniques, Hubei Normal University, Huangshi, Hubei 435000, People's Republic of China, ^bDepartment of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China, and ^cDepartment of Chemistry, Yicheng No. 1 Middle School, Xiangfan Yicheng, Hubei 441400, People's Republic of China
^*Correspondence e-mail: zqhu@mail.ccnu.edu.cn

(Received 6 November 2007; accepted 15 November 2007; online 6 December 2007)

The Schiff base ligand derived from the condensation of 3,5-dibromosalicylaldehyde and 1,2-phenylenediamine, in the presence of dimethylformamide, forms the centrosymmetric title neutral binuclear distorted complex, [Cd₂(C₂₀H₁₀Br₄N₂O₂)₂(C₃H₇NO)₂], with the two octahedral Cd atoms linked by two O atoms. All bond lengths and angles show normal values.

Related literature

For related literature, see: Elzbieta et al. (1964 ); Wang et al. (2003 ); Wu et al. (2005 ).

Experimental

Crystal data

[Cd₂(C₂₀H₁₀Br₄N₂O₂)₂(C₃H₇NO)₂]
M_r = 1630.87
Triclinic, $[P \overline 1]$
a = 9.6831 (8) Å
b = 12.0433 (10) Å
c = 12.4877 (10) Å
α = 95.942 (1)°
β = 108.822 (1)°
γ = 90.313 (1)°
V = 1369.82 (19) Å³
Z = 1
Mo Kα radiation
μ = 6.66 mm⁻¹
T = 296 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
11120 measured reflections
4716 independent reflections
2815 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.210
S = 1.04
4716 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 1.63 e Å⁻³
Δρ_min = −2.23 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cd1—O2	2.265 (6)
Cd1—O1	2.279 (6)
Cd1—O1ⁱ	2.341 (7)
Cd1—N2	2.352 (8)
Cd1—O3	2.371 (9)
Cd1—N1	2.391 (8)

O2—Cd1—O1	129.1 (3)
O2—Cd1—O1ⁱ	84.5 (2)
O1—Cd1—O1ⁱ	73.6 (3)
O2—Cd1—N2	80.5 (3)
O1—Cd1—N2	150.0 (3)
N2—Cd1—N1	71.6 (3)
Symmetry code: (i) -x, -y, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807059612/br2060sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807059612/br2060Isup2.hkl

checkCIF report

Comment top

The crystal structure and some properties of 4,4',6,6'-tetrabromo- 2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenolato Ni(II) and Zn(II) complex were previously reported by Wang et al. (2003) and Wu et al. (2005), respectively. We report here the synthesis and crystal structure of a novel binuclear complex {bis[N,N'-1,2-phenylenediaminebis(3,5-dibromosalicylideneiminato)]- bisdimethylformamide-diCadmium(II)}. In the title compound,every molecule forms a centro-symmetric dimer and each Cd atom is six-coordinated by one oxygen atom of dimethylformamide, two O and two amino N atom of the ligand 4,4',6,6'-tetrabromo-2,2'-[1,2-phenylenebis-(nitrilomethylidyne)]diphenol and the µ-O atom from another ligand,forming a distorted octahedron (Fig. 1).

Related literature top

For related literature, see: Elzbieta et al. (1964); Wang et al. (2003); Wu et al. (2005).

Experimental top

The title complex was synthesized in two stages. In the first stage, 3,5-dibromosalicylaldehyde was prepared according to Elzbieta et al. (1964). (1964). To ethanol (100 ml) containing 1,2-phenylenediamine (6 g), two mole equivalents of 3,5-dibromosalicylaldehyde in ethanol (50 ml) were slowly added with continuous stirring; the Schiff base molecule, viz. 4,4',6,6'-tetrabromo-2,2'-[1,2-phenylenebis(nitrilomethylidyne)]diphenol, precipitated immediately. In the second stage, the ligand (0.3 mmol), Cd(OAc)₂ (0.6 mmol), DMF (30 ml) were refluxed for 2 h. The hot solution was filtered and allowed to stand at room temperature undisturbed for about one month, resulting in yellow crystals.

Structure description top

For related literature, see: Elzbieta et al. (1964); Wang et al. (2003); Wu et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

Fig. 1. Molecular structure of (I) showing 30% probability displacement ellipsoids.

Bis{µ-4,4',6,6'-tetrabromo-2,2'-[o- phenylenebis(nitrilomethylidyne)]diphenolato}bis[(dimethylformamide)cadmium(II)] top

Crystal data top

[Cd₂(C₂₀H₁₀Br₄N₂O₂)₂(C₃H₇NO)₂]	Z = 1
M_r = 1630.87	F(000) = 776
Triclinic, P1	D_x = 1.977 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6831 (8) Å	Cell parameters from 3027 reflections
b = 12.0433 (10) Å	θ = 2.3–26.4°
c = 12.4877 (10) Å	µ = 6.66 mm⁻¹
α = 95.942 (1)°	T = 296 K
β = 108.822 (1)°	Block, yellow
γ = 90.313 (1)°	0.20 × 0.20 × 0.20 mm
V = 1369.82 (19) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2815 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
φ and ω scans	h = −11→11
11120 measured reflections	k = −14→14
4716 independent reflections	l = −14→14

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1219P)²] where P = (F_o² + 2F_c²)/3
4716 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 1.63 e Å⁻³
0 restraints	Δρ_min = −2.23 e Å⁻³

Crystal data top

[Cd₂(C₂₀H₁₀Br₄N₂O₂)₂(C₃H₇NO)₂]	γ = 90.313 (1)°
M_r = 1630.87	V = 1369.82 (19) Å³
Triclinic, P1	Z = 1
a = 9.6831 (8) Å	Mo Kα radiation
b = 12.0433 (10) Å	µ = 6.66 mm⁻¹
c = 12.4877 (10) Å	T = 296 K
α = 95.942 (1)°	0.20 × 0.20 × 0.20 mm
β = 108.822 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2815 reflections with I > 2σ(I)
11120 measured reflections	R_int = 0.062
4716 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.210	H-atom parameters constrained
S = 1.04	Δρ_max = 1.63 e Å⁻³
4716 reflections	Δρ_min = −2.23 e Å⁻³
309 parameters

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	U_iso*/U_eq
Cd1	0.11948 (8)	0.12544 (6)	0.51678 (6)	0.0395 (3)
Br1	0.4487 (2)	−0.23438 (14)	1.02145 (13)	0.0916 (6)
Br2	0.23171 (17)	−0.28244 (10)	0.53098 (11)	0.0675 (4)
Br3	0.44885 (19)	0.53322 (12)	0.20894 (13)	0.0840 (5)
Br4	0.07472 (16)	0.13462 (11)	0.09195 (10)	0.0688 (5)
C1	0.1356 (12)	0.3654 (9)	0.6670 (8)	0.043 (3)
C2	0.1149 (13)	0.4809 (10)	0.6945 (10)	0.055 (3)
H2	0.1184	0.5315	0.6438	0.066*
C3	0.0895 (15)	0.5198 (11)	0.7953 (11)	0.067 (4)
H3	0.0813	0.5958	0.8132	0.080*
C4	0.0764 (17)	0.4440 (12)	0.8695 (11)	0.078 (4)
H4	0.0541	0.4685	0.9349	0.093*
C5	0.0982 (14)	0.3268 (11)	0.8430 (10)	0.060 (3)
H5	0.0948	0.2766	0.8939	0.072*
C6	0.1244 (11)	0.2880 (8)	0.7418 (8)	0.038 (2)
C7	0.1996 (12)	0.1034 (10)	0.7944 (8)	0.048 (3)
H7	0.2190	0.1357	0.8690	0.057*
C8	0.2330 (12)	−0.0143 (9)	0.7800 (8)	0.046 (3)
C9	0.1989 (11)	−0.0823 (9)	0.6713 (9)	0.043 (3)
C10	0.2592 (12)	−0.1937 (9)	0.6746 (10)	0.047 (3)
C11	0.3300 (13)	−0.2379 (10)	0.7774 (10)	0.056 (3)
H11	0.3616	−0.3106	0.7773	0.068*
C12	0.3519 (14)	−0.1694 (11)	0.8801 (11)	0.061 (3)
C13	0.3081 (12)	−0.0600 (10)	0.8842 (10)	0.053 (3)
H13	0.3272	−0.0165	0.9538	0.063*
C14	0.2264 (12)	0.3819 (9)	0.5122 (9)	0.047 (3)
H14	0.2668	0.4505	0.5515	0.057*
C15	0.2428 (12)	0.3542 (8)	0.3983 (9)	0.043 (3)
C16	0.1701 (11)	0.2569 (8)	0.3189 (8)	0.040 (2)
C17	0.1859 (14)	0.2533 (10)	0.2058 (9)	0.052 (3)
C18	0.2647 (13)	0.3316 (10)	0.1731 (9)	0.054 (3)
H18	0.2704	0.3248	0.0998	0.065*
C19	0.3385 (13)	0.4247 (9)	0.2558 (10)	0.051 (3)
C20	0.3231 (13)	0.4366 (9)	0.3635 (10)	0.055 (3)
H20	0.3657	0.4991	0.4141	0.066*
C21	0.4950 (16)	0.1462 (13)	0.6135 (13)	0.076 (4)
H21	0.5067	0.2211	0.6046	0.091*
C22	0.7544 (17)	0.1575 (18)	0.7356 (15)	0.132 (8)
H22A	0.7803	0.1603	0.8169	0.198*
H22B	0.7512	0.2321	0.7146	0.198*
H22C	0.8259	0.1173	0.7107	0.198*
C23	0.591 (2)	−0.0177 (14)	0.7041 (16)	0.111 (6)
H23A	0.6012	−0.0188	0.7830	0.167*
H23B	0.6651	−0.0617	0.6865	0.167*
H23C	0.4965	−0.0480	0.6577	0.167*
N1	0.1447 (10)	0.1698 (8)	0.7134 (7)	0.047 (2)
N2	0.1608 (10)	0.3198 (7)	0.5632 (7)	0.045 (2)
N3	0.6088 (12)	0.0998 (10)	0.6810 (9)	0.069 (3)
O1	0.1178 (8)	−0.0490 (5)	0.5721 (6)	0.0445 (18)
O2	0.0985 (8)	0.1756 (6)	0.3426 (6)	0.0477 (19)
O3	0.3735 (9)	0.0995 (9)	0.5606 (9)	0.087 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0502 (5)	0.0319 (4)	0.0337 (5)	−0.0075 (3)	0.0083 (4)	0.0092 (3)
Br1	0.1109 (13)	0.0818 (11)	0.0657 (10)	0.0087 (9)	−0.0052 (9)	0.0452 (9)
Br2	0.0899 (10)	0.0448 (7)	0.0618 (8)	0.0056 (7)	0.0157 (7)	0.0085 (6)
Br3	0.1124 (12)	0.0685 (9)	0.0833 (10)	−0.0282 (9)	0.0447 (10)	0.0229 (8)
Br4	0.0918 (11)	0.0691 (9)	0.0404 (7)	−0.0234 (7)	0.0162 (7)	0.0018 (6)
C1	0.055 (7)	0.040 (6)	0.031 (5)	0.007 (5)	0.009 (5)	0.003 (5)
C2	0.064 (8)	0.045 (7)	0.057 (8)	0.004 (6)	0.021 (6)	0.007 (6)
C3	0.086 (10)	0.058 (8)	0.062 (8)	0.010 (7)	0.032 (8)	0.005 (7)
C4	0.101 (11)	0.087 (11)	0.054 (8)	0.028 (9)	0.039 (8)	0.000 (8)
C5	0.068 (8)	0.057 (8)	0.054 (8)	0.006 (6)	0.018 (7)	0.009 (6)
C6	0.040 (6)	0.039 (6)	0.034 (6)	0.008 (5)	0.007 (5)	0.008 (5)
C7	0.053 (7)	0.063 (8)	0.025 (5)	0.015 (6)	0.007 (5)	0.016 (5)
C8	0.060 (7)	0.041 (6)	0.030 (6)	−0.017 (5)	0.002 (5)	0.007 (5)
C9	0.033 (6)	0.050 (7)	0.044 (6)	−0.007 (5)	0.003 (5)	0.017 (5)
C10	0.048 (7)	0.036 (6)	0.055 (7)	−0.007 (5)	0.014 (6)	0.008 (5)
C11	0.062 (8)	0.040 (6)	0.066 (8)	−0.002 (6)	0.013 (7)	0.029 (6)
C12	0.060 (8)	0.062 (8)	0.054 (8)	0.000 (6)	−0.002 (6)	0.044 (7)
C13	0.052 (7)	0.051 (7)	0.049 (7)	−0.008 (6)	0.002 (6)	0.023 (6)
C14	0.059 (7)	0.029 (5)	0.049 (7)	0.004 (5)	0.009 (6)	0.010 (5)
C15	0.049 (6)	0.034 (6)	0.045 (6)	−0.001 (5)	0.010 (5)	0.017 (5)
C16	0.048 (6)	0.035 (6)	0.032 (5)	0.002 (5)	0.004 (5)	0.011 (5)
C17	0.071 (8)	0.053 (7)	0.037 (6)	0.009 (6)	0.017 (6)	0.023 (5)
C18	0.062 (8)	0.062 (8)	0.037 (6)	−0.011 (6)	0.012 (6)	0.012 (6)
C19	0.052 (7)	0.048 (7)	0.059 (8)	0.005 (5)	0.020 (6)	0.025 (6)
C20	0.073 (8)	0.031 (6)	0.056 (7)	−0.012 (6)	0.012 (7)	0.012 (5)
C21	0.066 (10)	0.071 (10)	0.090 (11)	0.003 (8)	0.020 (9)	0.022 (8)
C22	0.060 (11)	0.20 (2)	0.109 (15)	−0.039 (13)	−0.017 (10)	0.049 (15)
C23	0.108 (14)	0.094 (13)	0.135 (16)	0.037 (11)	0.034 (12)	0.045 (12)
N1	0.056 (6)	0.054 (6)	0.031 (5)	−0.006 (5)	0.013 (4)	0.002 (4)
N2	0.063 (6)	0.031 (5)	0.035 (5)	−0.015 (4)	0.007 (4)	0.006 (4)
N3	0.051 (7)	0.083 (8)	0.072 (8)	−0.002 (6)	0.016 (6)	0.015 (7)
O1	0.052 (5)	0.032 (4)	0.038 (4)	0.000 (3)	−0.006 (3)	0.020 (3)
O2	0.066 (5)	0.046 (4)	0.031 (4)	−0.015 (4)	0.016 (4)	0.006 (3)
O3	0.040 (5)	0.098 (8)	0.121 (9)	−0.001 (5)	0.021 (6)	0.013 (6)

Geometric parameters (Å, º) top

Cd1—O2	2.265 (6)	C10—C11	1.406 (15)
Cd1—O1	2.279 (6)	C11—C12	1.405 (17)
Cd1—O1ⁱ	2.341 (7)	C11—H11	0.9300
Cd1—N2	2.352 (8)	C12—C13	1.387 (17)
Cd1—O3	2.371 (9)	C13—H13	0.9300
Cd1—N1	2.391 (8)	C14—N2	1.313 (12)
Br1—C12	1.958 (11)	C14—C15	1.486 (15)
Br2—C10	1.929 (11)	C14—H14	0.9300
Br3—C19	1.933 (10)	C15—C20	1.441 (13)
Br4—C17	1.949 (12)	C15—C16	1.468 (14)
C1—C6	1.414 (13)	C16—O2	1.307 (11)
C1—C2	1.429 (15)	C16—C17	1.465 (14)
C1—N2	1.449 (13)	C17—C18	1.383 (15)
C2—C3	1.394 (16)	C18—C19	1.453 (16)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.399 (18)	C19—C20	1.394 (15)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.448 (18)	C21—O3	1.245 (16)
C4—H4	0.9300	C21—N3	1.320 (16)
C5—C6	1.401 (15)	C21—H21	0.9300
C5—H5	0.9300	C22—N3	1.486 (18)
C6—N1	1.460 (13)	C22—H22A	0.9600
C7—N1	1.331 (13)	C22—H22B	0.9600
C7—C8	1.463 (15)	C22—H22C	0.9600
C7—H7	0.9300	C23—N3	1.492 (19)
C8—C13	1.438 (14)	C23—H23A	0.9600
C8—C9	1.448 (15)	C23—H23B	0.9600
C9—O1	1.339 (12)	C23—H23C	0.9600
C9—C10	1.466 (15)	O1—Cd1ⁱ	2.341 (7)

O2—Cd1—O1	129.1 (3)	C12—C13—H13	120.3
O2—Cd1—O1ⁱ	84.5 (2)	C8—C13—H13	120.3
O1—Cd1—O1ⁱ	73.6 (3)	N2—C14—C15	126.8 (9)
O2—Cd1—N2	80.5 (3)	N2—C14—H14	116.6
O1—Cd1—N2	150.0 (3)	C15—C14—H14	116.6
O1ⁱ—Cd1—N2	120.4 (3)	C20—C15—C16	120.5 (10)
O2—Cd1—O3	92.4 (3)	C20—C15—C14	115.5 (9)
O1—Cd1—O3	83.4 (3)	C16—C15—C14	123.7 (9)
O1ⁱ—Cd1—O3	147.1 (3)	O2—C16—C17	119.8 (9)
N2—Cd1—O3	91.1 (3)	O2—C16—C15	125.5 (9)
O2—Cd1—N1	151.8 (3)	C17—C16—C15	114.6 (9)
O1—Cd1—N1	79.2 (3)	C18—C17—C16	124.8 (11)
O1ⁱ—Cd1—N1	106.3 (3)	C18—C17—Br4	118.6 (8)
N2—Cd1—N1	71.6 (3)	C16—C17—Br4	116.4 (8)
O3—Cd1—N1	91.7 (3)	C17—C18—C19	118.5 (10)
C6—C1—C2	119.1 (10)	C17—C18—H18	120.7
C6—C1—N2	116.5 (9)	C19—C18—H18	120.7
C2—C1—N2	124.3 (9)	C20—C19—C18	120.0 (9)
C3—C2—C1	121.7 (11)	C20—C19—Br3	121.9 (9)
C3—C2—H2	119.2	C18—C19—Br3	118.1 (8)
C1—C2—H2	119.2	C19—C20—C15	121.5 (10)
C2—C3—C4	119.8 (12)	C19—C20—H20	119.3
C2—C3—H3	120.1	C15—C20—H20	119.3
C4—C3—H3	120.1	O3—C21—N3	126.3 (14)
C3—C4—C5	119.0 (11)	O3—C21—H21	116.8
C3—C4—H4	120.5	N3—C21—H21	116.8
C5—C4—H4	120.5	N3—C22—H22A	109.5
C6—C5—C4	121.1 (11)	N3—C22—H22B	109.5
C6—C5—H5	119.5	H22A—C22—H22B	109.5
C4—C5—H5	119.5	N3—C22—H22C	109.5
C5—C6—C1	119.2 (10)	H22A—C22—H22C	109.5
C5—C6—N1	121.6 (9)	H22B—C22—H22C	109.5
C1—C6—N1	119.1 (9)	N3—C23—H23A	109.5
N1—C7—C8	127.6 (10)	N3—C23—H23B	109.5
N1—C7—H7	116.2	H23A—C23—H23B	109.5
C8—C7—H7	116.2	N3—C23—H23C	109.5
C13—C8—C9	120.7 (10)	H23A—C23—H23C	109.5
C13—C8—C7	114.5 (10)	H23B—C23—H23C	109.5
C9—C8—C7	124.7 (9)	C7—N1—C6	121.1 (9)
O1—C9—C8	124.0 (10)	C7—N1—Cd1	125.2 (7)
O1—C9—C10	120.1 (10)	C6—N1—Cd1	112.4 (6)
C8—C9—C10	115.8 (9)	C14—N2—C1	119.9 (9)
C11—C10—C9	122.3 (11)	C14—N2—Cd1	123.4 (7)
C11—C10—Br2	120.2 (9)	C1—N2—Cd1	115.6 (6)
C9—C10—Br2	117.5 (8)	C21—N3—C22	123.9 (13)
C12—C11—C10	118.4 (11)	C21—N3—C23	118.5 (12)
C12—C11—H11	120.8	C22—N3—C23	117.6 (14)
C10—C11—H11	120.8	C9—O1—Cd1	126.7 (6)
C13—C12—C11	122.8 (10)	C9—O1—Cd1ⁱ	119.4 (5)
C13—C12—Br1	120.0 (10)	Cd1—O1—Cd1ⁱ	106.4 (3)
C11—C12—Br1	117.2 (9)	C16—O2—Cd1	127.4 (6)
C12—C13—C8	119.4 (11)	C21—O3—Cd1	142.1 (10)

C6—C1—C2—C3	2.5 (18)	O1—Cd1—N1—C7	24.8 (9)
N2—C1—C2—C3	179.3 (11)	O1ⁱ—Cd1—N1—C7	93.9 (9)
C1—C2—C3—C4	−3 (2)	N2—Cd1—N1—C7	−148.7 (9)
C2—C3—C4—C5	4 (2)	O3—Cd1—N1—C7	−58.2 (9)
C3—C4—C5—C6	−3 (2)	O2—Cd1—N1—C6	10.3 (11)
C4—C5—C6—C1	2.6 (18)	O1—Cd1—N1—C6	−168.3 (7)
C4—C5—C6—N1	−179.2 (11)	O1ⁱ—Cd1—N1—C6	−99.1 (7)
C2—C1—C6—C5	−2.2 (16)	N2—Cd1—N1—C6	18.2 (6)
N2—C1—C6—C5	−179.2 (10)	O3—Cd1—N1—C6	108.8 (7)
C2—C1—C6—N1	179.6 (10)	C15—C14—N2—C1	−171.1 (10)
N2—C1—C6—N1	2.6 (14)	C15—C14—N2—Cd1	21.1 (15)
N1—C7—C8—C13	172.7 (10)	C6—C1—N2—C14	−153.9 (10)
N1—C7—C8—C9	−5.8 (18)	C2—C1—N2—C14	29.3 (16)
C13—C8—C9—O1	173.6 (9)	C6—C1—N2—Cd1	14.8 (12)
C7—C8—C9—O1	−7.9 (16)	C2—C1—N2—Cd1	−162.0 (9)
C13—C8—C9—C10	−6.4 (14)	O2—Cd1—N2—C14	−33.2 (8)
C7—C8—C9—C10	172.0 (10)	O1—Cd1—N2—C14	137.8 (8)
O1—C9—C10—C11	−172.2 (9)	O1ⁱ—Cd1—N2—C14	−111.0 (8)
C8—C9—C10—C11	7.8 (15)	O3—Cd1—N2—C14	59.1 (9)
O1—C9—C10—Br2	5.4 (12)	N1—Cd1—N2—C14	150.6 (9)
C8—C9—C10—Br2	−174.6 (7)	O2—Cd1—N2—C1	158.5 (8)
C9—C10—C11—C12	−4.4 (16)	O1—Cd1—N2—C1	−30.5 (11)
Br2—C10—C11—C12	178.1 (9)	O1ⁱ—Cd1—N2—C1	80.7 (8)
C10—C11—C12—C13	−0.7 (18)	O3—Cd1—N2—C1	−109.2 (8)
C10—C11—C12—Br1	179.3 (8)	N1—Cd1—N2—C1	−17.7 (7)
C11—C12—C13—C8	2.0 (18)	O3—C21—N3—C22	175.5 (15)
Br1—C12—C13—C8	−178.0 (8)	O3—C21—N3—C23	−4 (2)
C9—C8—C13—C12	1.9 (16)	C8—C9—O1—Cd1	38.3 (13)
C7—C8—C13—C12	−176.7 (10)	C10—C9—O1—Cd1	−141.6 (7)
N2—C14—C15—C20	−178.6 (11)	C8—C9—O1—Cd1ⁱ	−107.3 (9)
N2—C14—C15—C16	8.2 (18)	C10—C9—O1—Cd1ⁱ	72.7 (11)
C20—C15—C16—O2	177.7 (11)	O2—Cd1—O1—C9	142.4 (8)
C14—C15—C16—O2	−9.3 (17)	O1ⁱ—Cd1—O1—C9	−149.2 (10)
C20—C15—C16—C17	−0.6 (15)	N2—Cd1—O1—C9	−26.1 (11)
C14—C15—C16—C17	172.4 (10)	O3—Cd1—O1—C9	54.6 (8)
O2—C16—C17—C18	−176.9 (11)	N1—Cd1—O1—C9	−38.4 (8)
C15—C16—C17—C18	1.6 (17)	O2—Cd1—O1—Cd1ⁱ	−68.4 (4)
O2—C16—C17—Br4	7.9 (14)	O1ⁱ—Cd1—O1—Cd1ⁱ	0.0
C15—C16—C17—Br4	−173.7 (7)	N2—Cd1—O1—Cd1ⁱ	123.1 (5)
C16—C17—C18—C19	0.2 (19)	O3—Cd1—O1—Cd1ⁱ	−156.2 (4)
Br4—C17—C18—C19	175.4 (9)	N1—Cd1—O1—Cd1ⁱ	110.7 (3)
C17—C18—C19—C20	−3.1 (18)	C17—C16—O2—Cd1	157.1 (8)
C17—C18—C19—Br3	179.8 (9)	C15—C16—O2—Cd1	−21.2 (15)
C18—C19—C20—C15	4.1 (18)	O1—Cd1—O2—C16	−140.1 (8)
Br3—C19—C20—C15	−178.9 (9)	O1ⁱ—Cd1—O2—C16	156.2 (9)
C16—C15—C20—C19	−2.2 (17)	N2—Cd1—O2—C16	34.1 (9)
C14—C15—C20—C19	−175.7 (11)	O3—Cd1—O2—C16	−56.6 (9)
C8—C7—N1—C6	−176.7 (10)	N1—Cd1—O2—C16	41.7 (12)
C8—C7—N1—Cd1	−10.9 (16)	N3—C21—O3—Cd1	134.6 (14)
C5—C6—N1—C7	−28.6 (15)	O2—Cd1—O3—C21	99.7 (17)
C1—C6—N1—C7	149.5 (10)	O1—Cd1—O3—C21	−131.3 (17)
C5—C6—N1—Cd1	163.8 (9)	O1ⁱ—Cd1—O3—C21	−176.7 (14)
C1—C6—N1—Cd1	−18.1 (11)	N2—Cd1—O3—C21	19.2 (17)
O2—Cd1—N1—C7	−156.6 (8)	N1—Cd1—O3—C21	−52.4 (17)

Symmetry code: (i) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd₂(C₂₀H₁₀Br₄N₂O₂)₂(C₃H₇NO)₂]
M_r	1630.87
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	9.6831 (8), 12.0433 (10), 12.4877 (10)
α, β, γ (°)	95.942 (1), 108.822 (1), 90.313 (1)
V (Å³)	1369.82 (19)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	6.66
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11120, 4716, 2815
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.210, 1.04
No. of reflections	4716
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.63, −2.23

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top

Cd1—O2	2.265 (6)	Cd1—O3	2.371 (9)
Cd1—O1	2.279 (6)	Cd1—N1	2.391 (8)
Cd1—O1ⁱ	2.341 (7)	O1—Cd1ⁱ	2.341 (7)
Cd1—N2	2.352 (8)

O2—Cd1—O1	129.1 (3)	O2—Cd1—N2	80.5 (3)
O2—Cd1—O1ⁱ	84.5 (2)	O1—Cd1—N2	150.0 (3)
O1—Cd1—O1ⁱ	73.6 (3)	N2—Cd1—N1	71.6 (3)

Symmetry code: (i) −x, −y, −z+1.

Acknowledgements

This work was supported by the National Education Government of China (grant No. 20772042).

References

Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Elzbieta, C., Zygmunt, E. & Romuald, K. (1964). Diss. Pharm. 15, 369–378. Google Scholar
Sheldrick, G. M. (1990). Acta Cryst. A46, 467–473. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J., Bei, F. L. & Ma, W. X. (2003). Chin. J. Inorg. Chem. 19, 609–612. Google Scholar
Wu, Y., Hu, Z., Li, M. & Fu, X. (2005). Acta Cryst. E61, m1352–m1353. Web of Science CSD CrossRef IUCr Journals Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis{μ-4,4′,6,6′-tetra­bromo-2,2′-[o-phenyl­enebis(nitrilo­methyl­­idyne)]­diphenol­ato}­bis­­[(di­methyl­formamide)cadmium(II)]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{μ-4,4′,6,6′-tetrabromo-2,2′-[o-phenylenebis(nitrilomethylidyne)]diphenolato}bis[(dimethylformamide)cadmium(II)]