Bis(μ-4-bromo­benzoato)-κ3O,O′:O′;O:O,O′-bis­[μ-1,3-bis­(pyridin-4-yl)propane-κ2N:N′]bis­[(4-bromo­benzoato-κ2O,O′)cadmium]

Liu, D.; Zi, Y.-Q.; Ng, S.W.

doi:10.1107/S1600536811043996

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page m1621

doi:10.1107/S1600536811043996

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Bis(μ-4-bromobenzoato)-κ³O,O′:O′;O:O,O′-bis[μ-1,3-bis(pyridin-4-yl)propane-κ²N:N′]bis[(4-bromobenzoato-κ²O,O′)cadmium]

Dong Liu,^a ^* Yan-Qin Zi ^a and Seik Weng Ng ^b,^c

^aCollege of Chemistry and Materials Science, Huaibei Normal University, Huaibei 235000, Anhui, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: dongliu@chnu.edu.cn

(Received 6 October 2011; accepted 23 October 2011; online 29 October 2011)

The dinuclear complex, [Cd₂(C₇H₄BrO₂)₄(C₁₃H₁₄N₂)₂], lies on a twofold rotation axis crossing midway between the two metal atoms. The Cd^II cation is seven-coordinated with a geometry that can be considered as distorted pentagonal bipyramidal, with the N atom of the N-heterocyclic units occupying the apical sites and the O atoms of the 4-bromobenzoate units in the equatorial plane. The middle methylene group of the 1,3-bis(4-pyridyl)propane ligands is located outside of the twofold rotation axis and consequently is disordered over two sites around this symmetry element with fixed occupancies factors of 0.5.

Related literature

For related structures, see: Liu et al. (2011 ). For another complex with a dinuclear seven-coordinate Cd(II) atom, see: Ranjbar et al. (2002 ); Wang et al. (2006 ).

Experimental

Crystal data

[Cd₂(C₇H₄BrO₂)₄(C₁₃H₁₄N₂)₂]
M_r = 1421.35
Tetragonal, P 4₃ 2₁ 2
a = 13.7829 (10) Å
c = 27.8235 (17) Å
V = 5285.6 (5) Å³
Z = 4
Mo Kα radiation
μ = 3.89 mm⁻¹
T = 223 K
0.45 × 0.40 × 0.35 mm

Data collection

Rigaku Mercury area-detector diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.174, T_max = 0.256
25017 measured reflections
6020 independent reflections
5452 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.104
S = 1.05
6020 reflections
334 parameters
34 restraints
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.71 e Å⁻³
Absolute structure: Flack (1983), 2533 Friedel pairs
Flack parameter: 0.006 (12)

Data collection: CrystalClear (Rigaku, 2001 ); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811043996/lr2033sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811043996/lr2033Isup2.hkl

checkCIF report

Comment top

The crystal structures of coordination compounds having flexible N-donor ligands are generally different from those having rigid N-donor ligands because these flexible ligands can adopt more than one conformation. The title adduct, [Cd₂(C₇H₄O₂Br)₄(C₁₃H₁₄N₂)₂] (Scheme I), is assembled from Cd(II) bis(4-bromobenzoate) and 1,3-bis(4-pyridyl)propane. This study represents an extension of our previous one (Liu et al., 2011).

The complex, which features two Cd^II atoms, is lying on a twofold crystallographic rotation axis crossing midway between the two metallic atoms. Each Cd^II atom is seven coordinated with an geometry that can be considered as a distorted pentagonal bipyramid, with the nitrogen atom of the N-heterocycle units occupying the apical sites and the oxygen atoms of the p-bromobenzoate units in the ecuatorial plane of each coordination bypiramide (Fig. 1). The middle methylene groups of the 1,3-bis(4-pyridyl)propane ligands are located outside of the binary crystallographic axis and consequently are disordered between two sites around this symmetry element with fixed occupancies factors of 0.5.

Related literature top

For related structures, see: Liu et al. (2011). For another complex with a dinuclear seven-coordinate Cd(II) atom, see: Ranjbar et al. (2002); Wang et al. (2006).

Experimental top

To a 10 mL Pyrex glass tube was loaded Cd(NO₃)₂.4H₂O (31 mg, 0.1 mmol), 4-bromobenzoic acid (40 mg, 0.2 mmol), 1,3-bis(4-pyridyl)propane (20 mg, 0.1 mmol) and 3 ml of water. The tube was sealed and heated in an oven to 423 K for three days. It was then cooled to ambient temperature at the rate of 5 K h^-1 to yield colorless crystals. These were washed with water/ethanol and dried; yield: 54 mg (76% yield based on Cd). Analysis: Calcd. for C₅₄H₄₄Br₄Cd₂N₄O₈: C, 45.63; H, 3.12; N, 3.94%. Found: C, 45.83; H, 2.94; N, 3.88%.

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Coordination environment of Cd^II with non-hydrogen atoms represented by thermal ellipsoids drawn at the 30% probability level;, hydrogen atoms are drawn as spheres of arbitrary radius. The unlabeled atoms are related to the labeled ones by y, x, 1 - z.

Bis(µ-4-bromobenzoato)-κ³O,O':O';O:O, O'-bis[µ-1,3-bis(pyridin-4-yl)propane-κ²N:N']bis[(4- bromobenzoato-κ²O,O')cadmium] top

Crystal data top

[Cd₂(C₇H₄BrO₂)₄(C₁₃H₁₄N₂)₂]	D_x = 1.786 Mg m⁻³
M_r = 1421.35	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P4₃2₁2	Cell parameters from 18739 reflections
Hall symbol: P 4nw 2abw	θ = 3.0–27.5°
a = 13.7829 (10) Å	µ = 3.89 mm⁻¹
c = 27.8235 (17) Å	T = 223 K
V = 5285.6 (5) Å³	Block, colorless
Z = 4	0.45 × 0.40 × 0.35 mm
F(000) = 2784

Data collection top

Rigaku Mercury area-detector diffractometer	6020 independent reflections
Radiation source: fine-focus sealed tube	5452 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −17→15
T_min = 0.174, T_max = 0.256	k = −14→17
25017 measured reflections	l = −36→34

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0507P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
6020 reflections	Δρ_max = 0.73 e Å⁻³
334 parameters	Δρ_min = −0.71 e Å⁻³
34 restraints	Absolute structure: Flack (1983), 2533 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.006 (12)

Crystal data top

[Cd₂(C₇H₄BrO₂)₄(C₁₃H₁₄N₂)₂]	Z = 4
M_r = 1421.35	Mo Kα radiation
Tetragonal, P4₃2₁2	µ = 3.89 mm⁻¹
a = 13.7829 (10) Å	T = 223 K
c = 27.8235 (17) Å	0.45 × 0.40 × 0.35 mm
V = 5285.6 (5) Å³

Data collection top

Rigaku Mercury area-detector diffractometer	6020 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	5452 reflections with I > 2σ(I)
T_min = 0.174, T_max = 0.256	R_int = 0.051
25017 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.104	Δρ_max = 0.73 e Å⁻³
S = 1.05	Δρ_min = −0.71 e Å⁻³
6020 reflections	Absolute structure: Flack (1983), 2533 Friedel pairs
334 parameters	Absolute structure parameter: 0.006 (12)
34 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.28537 (3)	0.30187 (3)	0.571507 (12)	0.03592 (10)
Br1	0.31290 (6)	0.12444 (5)	0.87743 (2)	0.0635 (2)
Br2	−0.11352 (5)	0.71348 (5)	0.41927 (2)	0.05446 (17)
N1	0.4148 (3)	0.4080 (3)	0.56841 (16)	0.0429 (11)
N2	0.1775 (3)	0.1737 (3)	0.56787 (15)	0.0396 (10)
O1	0.2543 (3)	0.3183 (3)	0.65343 (12)	0.0503 (10)
O2	0.3615 (3)	0.2054 (3)	0.63554 (12)	0.0456 (9)
O3	0.1690 (3)	0.4235 (3)	0.56093 (13)	0.0482 (10)
O4	0.2200 (3)	0.3720 (3)	0.49044 (12)	0.0427 (8)
C1	0.5048 (4)	0.3806 (5)	0.5593 (3)	0.0567 (16)
H1	0.5180	0.3146	0.5568	0.068*
C2	0.5805 (5)	0.4457 (5)	0.5532 (3)	0.072 (2)
H2	0.6428	0.4229	0.5470	0.086*
C3	0.5639 (5)	0.5433 (5)	0.5562 (3)	0.072 (2)
C4	0.4708 (6)	0.5709 (5)	0.5675 (3)	0.071 (2)
H4	0.4562	0.6365	0.5707	0.086*
C5	0.3986 (5)	0.5025 (4)	0.5741 (3)	0.0571 (17)
H5	0.3368	0.5232	0.5827	0.069*
C6	0.6408 (7)	0.6190 (7)	0.54516 (18)	0.112 (3)
H6A	0.6119	0.6825	0.5497	0.135*
H6B	0.6920	0.6125	0.5689	0.135*
C7	0.6851 (8)	0.6173 (12)	0.4982 (3)	0.097 (6)	0.50
H7A	0.7127	0.5533	0.4933	0.117*	0.50
H7B	0.7384	0.6633	0.4983	0.117*	0.50
C8	0.2078 (4)	0.0851 (4)	0.5583 (2)	0.0527 (15)
H8	0.2742	0.0747	0.5554	0.063*
C9	0.1461 (5)	0.0068 (5)	0.5524 (3)	0.0592 (18)
H9	0.1707	−0.0550	0.5468	0.071*
C10	0.0476 (4)	0.0221 (5)	0.5549 (3)	0.0595 (17)
C11	0.0170 (4)	0.1122 (5)	0.5678 (3)	0.0570 (16)
H11	−0.0487	0.1237	0.5730	0.068*
C12	0.0826 (4)	0.1862 (5)	0.5731 (2)	0.0484 (14)
H12	0.0596	0.2478	0.5807	0.058*
C13	−0.0237 (5)	−0.0588 (5)	0.54387 (18)	0.085 (3)
H13A	−0.0101	−0.1120	0.5657	0.102*
H13B	−0.0882	−0.0352	0.5515	0.102*
C14	−0.0264 (11)	−0.0976 (7)	0.4959 (3)	0.079 (4)	0.50
H14A	−0.0705	−0.1524	0.4954	0.095*	0.50
H14B	0.0377	−0.1216	0.4878	0.095*	0.50
C15	0.3081 (4)	0.2494 (4)	0.66474 (18)	0.0375 (11)
C16	0.3087 (3)	0.2182 (4)	0.71718 (16)	0.0332 (10)
C17	0.3666 (4)	0.1423 (4)	0.7316 (2)	0.0450 (13)
H17	0.4041	0.1095	0.7090	0.054*
C18	0.3697 (5)	0.1144 (4)	0.7793 (2)	0.0470 (14)
H18	0.4103	0.0645	0.7895	0.056*
C19	0.3100 (4)	0.1637 (4)	0.81186 (18)	0.0410 (12)
C20	0.2518 (4)	0.2390 (4)	0.79782 (18)	0.0432 (13)
H20	0.2134	0.2712	0.8202	0.052*
C21	0.2507 (4)	0.2665 (4)	0.7503 (2)	0.0405 (11)
H21	0.2111	0.3173	0.7403	0.049*
C22	0.1681 (4)	0.4273 (4)	0.51581 (17)	0.0327 (10)
C23	0.1022 (3)	0.4995 (3)	0.49208 (17)	0.0314 (10)
C24	0.1013 (4)	0.5092 (4)	0.44265 (18)	0.0380 (11)
H24	0.1431	0.4716	0.4241	0.046*
C25	0.0382 (4)	0.5750 (4)	0.41988 (19)	0.0409 (12)
H25	0.0379	0.5822	0.3866	0.049*
C26	−0.0224 (4)	0.6278 (4)	0.4483 (2)	0.0408 (12)
C27	−0.0225 (4)	0.6223 (4)	0.4981 (2)	0.0415 (12)
H27	−0.0638	0.6609	0.5164	0.050*
C28	0.0419 (4)	0.5564 (4)	0.52030 (19)	0.0408 (12)
H28	0.0439	0.5512	0.5536	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0413 (2)	0.0398 (2)	0.02666 (17)	0.00572 (16)	−0.00150 (14)	0.00022 (14)
Br1	0.0817 (5)	0.0768 (4)	0.0321 (3)	0.0083 (4)	−0.0002 (3)	0.0118 (3)
Br2	0.0561 (3)	0.0527 (3)	0.0546 (3)	0.0111 (3)	−0.0103 (3)	0.0124 (3)
N1	0.045 (2)	0.044 (2)	0.040 (2)	0.002 (2)	−0.001 (2)	−0.009 (2)
N2	0.039 (2)	0.043 (2)	0.037 (2)	0.0020 (19)	−0.0006 (19)	0.003 (2)
O1	0.064 (3)	0.055 (2)	0.0320 (19)	0.023 (2)	0.0008 (17)	0.0043 (17)
O2	0.051 (2)	0.057 (2)	0.0297 (18)	0.014 (2)	0.0039 (16)	−0.0019 (17)
O3	0.057 (2)	0.061 (2)	0.0266 (19)	0.0199 (19)	0.0005 (18)	0.0005 (18)
O4	0.050 (2)	0.045 (2)	0.0339 (18)	0.0106 (18)	0.0011 (17)	0.0015 (16)
C1	0.049 (3)	0.045 (3)	0.076 (5)	0.006 (3)	−0.007 (3)	−0.013 (3)
C2	0.038 (3)	0.062 (4)	0.115 (7)	−0.004 (3)	−0.005 (4)	−0.002 (4)
C3	0.061 (4)	0.050 (4)	0.106 (6)	−0.015 (3)	−0.021 (4)	−0.006 (4)
C4	0.076 (5)	0.035 (3)	0.102 (6)	0.001 (3)	−0.011 (5)	−0.011 (4)
C5	0.061 (4)	0.046 (3)	0.064 (4)	0.008 (3)	−0.005 (3)	−0.020 (3)
C6	0.087 (6)	0.080 (5)	0.170 (8)	−0.017 (5)	−0.041 (6)	0.005 (6)
C7	0.083 (8)	0.091 (9)	0.118 (10)	−0.022 (7)	0.011 (8)	−0.012 (8)
C8	0.040 (3)	0.045 (3)	0.073 (4)	0.003 (3)	−0.006 (3)	−0.006 (3)
C9	0.047 (3)	0.045 (3)	0.085 (5)	0.007 (3)	0.009 (3)	−0.006 (3)
C10	0.044 (3)	0.056 (4)	0.078 (5)	−0.006 (3)	0.004 (3)	0.008 (4)
C11	0.041 (3)	0.056 (4)	0.075 (5)	−0.002 (3)	0.018 (3)	0.000 (4)
C12	0.046 (3)	0.048 (3)	0.050 (3)	0.003 (3)	0.009 (3)	−0.005 (3)
C13	0.054 (4)	0.062 (4)	0.140 (7)	−0.012 (4)	−0.001 (5)	0.017 (5)
C14	0.078 (8)	0.063 (7)	0.097 (9)	−0.023 (6)	0.005 (7)	−0.010 (7)
C15	0.037 (2)	0.041 (3)	0.034 (3)	0.001 (2)	−0.003 (2)	−0.001 (2)
C16	0.033 (2)	0.041 (2)	0.025 (2)	0.005 (2)	−0.0024 (19)	0.000 (2)
C17	0.052 (3)	0.047 (3)	0.036 (3)	0.017 (3)	−0.003 (2)	−0.003 (2)
C18	0.062 (4)	0.043 (3)	0.036 (3)	0.010 (3)	−0.004 (3)	0.007 (2)
C19	0.047 (3)	0.047 (3)	0.029 (2)	−0.002 (3)	−0.002 (2)	0.004 (2)
C20	0.049 (3)	0.048 (3)	0.033 (3)	0.008 (3)	0.007 (2)	0.000 (2)
C21	0.043 (3)	0.042 (3)	0.036 (3)	0.012 (2)	0.002 (2)	0.002 (2)
C22	0.034 (2)	0.032 (2)	0.032 (3)	−0.0013 (19)	0.002 (2)	0.002 (2)
C23	0.035 (3)	0.029 (2)	0.029 (2)	−0.0025 (19)	0.004 (2)	0.0007 (19)
C24	0.037 (3)	0.043 (3)	0.034 (3)	−0.004 (2)	0.003 (2)	0.000 (2)
C25	0.048 (3)	0.044 (3)	0.030 (3)	−0.001 (2)	−0.002 (2)	0.004 (2)
C26	0.046 (3)	0.032 (3)	0.044 (3)	−0.004 (2)	−0.004 (2)	0.002 (2)
C27	0.044 (3)	0.039 (3)	0.041 (3)	0.004 (2)	−0.001 (2)	0.000 (2)
C28	0.051 (3)	0.042 (3)	0.029 (2)	0.004 (2)	−0.003 (2)	0.000 (2)

Geometric parameters (Å, º) top

Cd1—N1	2.309 (5)	C9—C10	1.375 (9)
Cd1—N2	2.311 (5)	C9—H9	0.9300
Cd1—O1	2.330 (3)	C10—C11	1.360 (9)
Cd1—O3	2.338 (4)	C10—C13	1.518 (7)
Cd1—O4ⁱ	2.381 (3)	C11—C12	1.371 (9)
Cd1—O2	2.458 (4)	C11—H11	0.9300
Cd1—O4	2.614 (3)	C12—H12	0.9300
Br1—C19	1.903 (5)	C13—C14	1.439 (8)
Br2—C26	1.904 (5)	C13—C14ⁱ	1.568 (9)
N1—C1	1.323 (7)	C13—H13A	0.9700
N1—C5	1.331 (7)	C13—H13B	0.9700
N2—C8	1.318 (7)	C14—C13ⁱ	1.568 (9)
N2—C12	1.328 (7)	C14—H14A	0.9700
O1—C15	1.245 (6)	C14—H14B	0.9700
O2—C15	1.253 (6)	C15—C16	1.521 (6)
O3—C22	1.256 (6)	C16—C17	1.376 (7)
O4—C22	1.262 (6)	C16—C21	1.390 (7)
O4—Cd1ⁱ	2.381 (3)	C17—C18	1.383 (8)
C1—C2	1.386 (9)	C17—H17	0.9300
C1—H1	0.9300	C18—C19	1.400 (8)
C2—C3	1.368 (10)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.368 (8)
C3—C4	1.374 (10)	C20—C21	1.376 (7)
C3—C6	1.519 (7)	C20—H20	0.9300
C4—C5	1.383 (10)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.500 (7)
C5—H5	0.9300	C23—C24	1.382 (7)
C6—C7	1.441 (8)	C23—C28	1.387 (7)
C6—C7ⁱ	1.547 (9)	C24—C25	1.408 (8)
C6—H6A	0.9700	C24—H24	0.9300
C6—H6B	0.9700	C25—C26	1.360 (8)
C7—C6ⁱ	1.547 (9)	C25—H25	0.9300
C7—H7A	0.9700	C26—C27	1.389 (8)
C7—H7B	0.9700	C27—C28	1.412 (7)
C8—C9	1.385 (8)	C27—H27	0.9300
C8—H8	0.9300	C28—H28	0.9300

N1—Cd1—N2	168.48 (15)	C10—C9—C8	118.8 (6)
N1—Cd1—O1	96.70 (16)	C10—C9—H9	120.6
N2—Cd1—O1	89.95 (16)	C8—C9—H9	120.6
N1—Cd1—O3	94.06 (16)	C11—C10—C9	117.4 (6)
N2—Cd1—O3	95.80 (15)	C11—C10—C13	121.5 (6)
O1—Cd1—O3	85.85 (13)	C9—C10—C13	121.1 (6)
N1—Cd1—O4ⁱ	83.45 (15)	C10—C11—C12	120.2 (6)
N2—Cd1—O4ⁱ	85.92 (15)	C10—C11—H11	119.9
O1—Cd1—O4ⁱ	147.81 (12)	C12—C11—H11	119.9
O3—Cd1—O4ⁱ	126.32 (12)	N2—C12—C11	122.8 (6)
N1—Cd1—O2	92.32 (15)	N2—C12—H12	118.6
N2—Cd1—O2	83.84 (14)	C11—C12—H12	118.6
O1—Cd1—O2	54.69 (12)	C14—C13—C10	118.5 (7)
O3—Cd1—O2	140.51 (12)	C14—C13—C14ⁱ	55.6 (10)
O4ⁱ—Cd1—O2	93.12 (12)	C10—C13—C14ⁱ	110.7 (7)
N1—Cd1—O4	89.98 (14)	C14—C13—H13A	107.7
N2—Cd1—O4	91.32 (14)	C10—C13—H13A	107.7
O1—Cd1—O4	138.15 (12)	C14ⁱ—C13—H13A	141.4
O3—Cd1—O4	52.42 (11)	C14—C13—H13B	107.7
O4ⁱ—Cd1—O4	73.93 (13)	C10—C13—H13B	107.7
O2—Cd1—O4	166.50 (11)	C14ⁱ—C13—H13B	57.6
N1—Cd1—C15	96.62 (15)	H13A—C13—H13B	107.1
N2—Cd1—C15	84.99 (15)	C13—C14—C13ⁱ	114.9 (8)
O1—Cd1—C15	27.28 (14)	C13—C14—H14A	108.5
O3—Cd1—C15	113.01 (14)	C13ⁱ—C14—H14A	108.5
O4ⁱ—Cd1—C15	120.56 (14)	C13—C14—H14B	108.5
O2—Cd1—C15	27.50 (13)	C13ⁱ—C14—H14B	108.5
O4—Cd1—C15	164.60 (14)	H14A—C14—H14B	107.5
C1—N1—C5	117.4 (6)	O1—C15—O2	123.7 (5)
C1—N1—Cd1	123.4 (4)	O1—C15—C16	117.5 (5)
C5—N1—Cd1	119.1 (4)	O2—C15—C16	118.8 (4)
C8—N2—C12	117.1 (5)	O1—C15—Cd1	59.1 (3)
C8—N2—Cd1	120.8 (4)	O2—C15—Cd1	65.0 (3)
C12—N2—Cd1	122.0 (4)	C16—C15—Cd1	173.6 (3)
C15—O1—Cd1	93.6 (3)	C17—C16—C21	120.3 (5)
C15—O2—Cd1	87.5 (3)	C17—C16—C15	119.9 (5)
C22—O3—Cd1	99.4 (3)	C21—C16—C15	119.8 (4)
C22—O4—Cd1ⁱ	167.6 (3)	C16—C17—C18	120.6 (5)
C22—O4—Cd1	86.3 (3)	C16—C17—H17	119.7
Cd1ⁱ—O4—Cd1	106.03 (13)	C18—C17—H17	119.7
N1—C1—C2	123.0 (6)	C17—C18—C19	117.9 (5)
N1—C1—H1	118.5	C17—C18—H18	121.1
C2—C1—H1	118.5	C19—C18—H18	121.1
C3—C2—C1	120.2 (6)	C20—C19—C18	121.9 (5)
C3—C2—H2	119.9	C20—C19—Br1	120.1 (4)
C1—C2—H2	119.9	C18—C19—Br1	118.0 (4)
C2—C3—C4	116.3 (6)	C19—C20—C21	119.4 (5)
C2—C3—C6	123.1 (7)	C19—C20—H20	120.3
C4—C3—C6	120.5 (7)	C21—C20—H20	120.3
C3—C4—C5	120.9 (6)	C20—C21—C16	119.9 (5)
C3—C4—H4	119.6	C20—C21—H21	120.1
C5—C4—H4	119.6	C16—C21—H21	120.1
N1—C5—C4	122.1 (6)	O3—C22—O4	121.8 (5)
N1—C5—H5	119.0	O3—C22—C23	118.3 (4)
C4—C5—H5	119.0	O4—C22—C23	119.9 (4)
C7—C6—C3	117.9 (8)	C24—C23—C28	120.2 (5)
C7—C6—C7ⁱ	52.5 (12)	C24—C23—C22	120.5 (5)
C3—C6—C7ⁱ	114.6 (8)	C28—C23—C22	119.3 (4)
C7—C6—H6A	107.8	C23—C24—C25	121.0 (5)
C3—C6—H6A	107.8	C23—C24—H24	119.5
C7ⁱ—C6—H6A	58.9	C25—C24—H24	119.5
C7—C6—H6B	107.8	C26—C25—C24	117.6 (5)
C3—C6—H6B	107.8	C26—C25—H25	121.2
C7ⁱ—C6—H6B	137.6	C24—C25—H25	121.2
H6A—C6—H6B	107.2	C25—C26—C27	123.5 (5)
C6—C7—C6ⁱ	117.0 (9)	C25—C26—Br2	119.4 (4)
C6—C7—H7A	108.1	C27—C26—Br2	117.2 (4)
C6ⁱ—C7—H7A	108.0	C26—C27—C28	118.1 (5)
C6—C7—H7B	108.0	C26—C27—H27	121.0
C6ⁱ—C7—H7B	108.0	C28—C27—H27	121.0
H7A—C7—H7B	107.3	C23—C28—C27	119.6 (5)
N2—C8—C9	123.4 (6)	C23—C28—H28	120.2
N2—C8—H8	118.3	C27—C28—H28	120.2
C9—C8—H8	118.3

N2—Cd1—N1—C1	−11.9 (10)	C4—C3—C6—C7	−119.0 (12)
O1—Cd1—N1—C1	113.0 (5)	C2—C3—C6—C7ⁱ	116.5 (12)
O3—Cd1—N1—C1	−160.7 (5)	C4—C3—C6—C7ⁱ	−60.0 (12)
O4ⁱ—Cd1—N1—C1	−34.6 (5)	C3—C6—C7—C6ⁱ	65.9 (15)
O2—Cd1—N1—C1	58.3 (5)	C7ⁱ—C6—C7—C6ⁱ	−34.9 (13)
O4—Cd1—N1—C1	−108.4 (5)	C12—N2—C8—C9	1.7 (9)
C15—Cd1—N1—C1	85.6 (5)	Cd1—N2—C8—C9	−175.4 (5)
N2—Cd1—N1—C5	165.2 (7)	N2—C8—C9—C10	2.3 (11)
O1—Cd1—N1—C5	−69.9 (5)	C8—C9—C10—C11	−6.3 (11)
O3—Cd1—N1—C5	16.4 (5)	C8—C9—C10—C13	174.0 (6)
O4ⁱ—Cd1—N1—C5	142.5 (5)	C9—C10—C11—C12	6.4 (11)
O2—Cd1—N1—C5	−124.6 (5)	C13—C10—C11—C12	−173.9 (6)
O4—Cd1—N1—C5	68.7 (5)	C8—N2—C12—C11	−1.7 (9)
C15—Cd1—N1—C5	−97.3 (5)	Cd1—N2—C12—C11	175.4 (5)
N1—Cd1—N2—C8	11.7 (10)	C10—C11—C12—N2	−2.5 (11)
O1—Cd1—N2—C8	−113.8 (5)	C11—C10—C13—C14	115.9 (10)
O3—Cd1—N2—C8	160.4 (5)	C9—C10—C13—C14	−64.4 (12)
O4ⁱ—Cd1—N2—C8	34.3 (5)	C11—C10—C13—C14ⁱ	54.7 (10)
O2—Cd1—N2—C8	−59.3 (5)	C9—C10—C13—C14ⁱ	−125.6 (9)
O4—Cd1—N2—C8	108.1 (5)	C10—C13—C14—C13ⁱ	−63.9 (13)
C15—Cd1—N2—C8	−86.9 (5)	C14ⁱ—C13—C14—C13ⁱ	32.8 (11)
N1—Cd1—N2—C12	−165.3 (7)	Cd1—O1—C15—O2	6.5 (6)
O1—Cd1—N2—C12	69.2 (4)	Cd1—O1—C15—C16	−173.8 (4)
O3—Cd1—N2—C12	−16.6 (5)	Cd1—O2—C15—O1	−6.1 (5)
O4ⁱ—Cd1—N2—C12	−142.7 (5)	Cd1—O2—C15—C16	174.2 (4)
O2—Cd1—N2—C12	123.7 (4)	N1—Cd1—C15—O1	91.8 (3)
O4—Cd1—N2—C12	−68.9 (4)	N2—Cd1—C15—O1	−99.7 (3)
C15—Cd1—N2—C12	96.1 (5)	O3—Cd1—C15—O1	−5.5 (4)
N1—Cd1—O1—C15	−91.5 (3)	O4ⁱ—Cd1—C15—O1	178.1 (3)
N2—Cd1—O1—C15	79.1 (3)	O2—Cd1—C15—O1	174.0 (5)
O3—Cd1—O1—C15	174.9 (3)	O4—Cd1—C15—O1	−23.0 (7)
O4ⁱ—Cd1—O1—C15	−3.1 (5)	N1—Cd1—C15—O2	−82.3 (3)
O2—Cd1—O1—C15	−3.4 (3)	N2—Cd1—C15—O2	86.3 (3)
O4—Cd1—O1—C15	171.0 (3)	O1—Cd1—C15—O2	−174.0 (5)
N1—Cd1—O2—C15	99.9 (3)	O3—Cd1—C15—O2	−179.5 (3)
N2—Cd1—O2—C15	−91.0 (3)	O4ⁱ—Cd1—C15—O2	4.0 (4)
O1—Cd1—O2—C15	3.3 (3)	O4—Cd1—C15—O2	162.9 (4)
O3—Cd1—O2—C15	0.7 (4)	O1—C15—C16—C17	179.8 (5)
O4ⁱ—Cd1—O2—C15	−176.5 (3)	O2—C15—C16—C17	−0.5 (8)
O4—Cd1—O2—C15	−160.5 (5)	O1—C15—C16—C21	−0.1 (7)
N1—Cd1—O3—C22	86.1 (4)	O2—C15—C16—C21	179.6 (5)
N2—Cd1—O3—C22	−88.0 (4)	C21—C16—C17—C18	−1.5 (9)
O1—Cd1—O3—C22	−177.5 (4)	C15—C16—C17—C18	178.5 (5)
O4ⁱ—Cd1—O3—C22	1.2 (4)	C16—C17—C18—C19	2.0 (9)
O2—Cd1—O3—C22	−175.3 (3)	C17—C18—C19—C20	−1.7 (9)
O4—Cd1—O3—C22	−0.8 (3)	C17—C18—C19—Br1	179.3 (5)
C15—Cd1—O3—C22	−175.0 (3)	C18—C19—C20—C21	0.9 (9)
N1—Cd1—O4—C22	−94.4 (3)	Br1—C19—C20—C21	179.9 (4)
N2—Cd1—O4—C22	97.1 (3)	C19—C20—C21—C16	−0.4 (8)
O1—Cd1—O4—C22	5.7 (4)	C17—C16—C21—C20	0.7 (8)
O3—Cd1—O4—C22	0.8 (3)	C15—C16—C21—C20	−179.4 (5)
O4ⁱ—Cd1—O4—C22	−177.6 (3)	Cd1—O3—C22—O4	1.5 (6)
O2—Cd1—O4—C22	165.7 (5)	Cd1—O3—C22—C23	−179.1 (4)
C15—Cd1—O4—C22	21.3 (7)	Cd1ⁱ—O4—C22—O3	179.1 (14)
N1—Cd1—O4—Cd1ⁱ	85.51 (17)	Cd1—O4—C22—O3	−1.3 (5)
N2—Cd1—O4—Cd1ⁱ	−83.04 (17)	Cd1ⁱ—O4—C22—C23	0 (2)
O1—Cd1—O4—Cd1ⁱ	−174.44 (17)	Cd1—O4—C22—C23	179.3 (4)
O3—Cd1—O4—Cd1ⁱ	−179.3 (2)	O3—C22—C23—C24	177.4 (5)
O4ⁱ—Cd1—O4—Cd1ⁱ	2.3 (2)	O4—C22—C23—C24	−3.1 (8)
O2—Cd1—O4—Cd1ⁱ	−14.4 (7)	O3—C22—C23—C28	−2.7 (7)
C15—Cd1—O4—Cd1ⁱ	−158.8 (5)	O4—C22—C23—C28	176.8 (5)
C5—N1—C1—C2	−3.2 (11)	C28—C23—C24—C25	−1.4 (8)
Cd1—N1—C1—C2	174.0 (6)	C22—C23—C24—C25	178.5 (5)
N1—C1—C2—C3	−0.5 (13)	C23—C24—C25—C26	−0.6 (8)
C1—C2—C3—C4	2.8 (13)	C24—C25—C26—C27	2.3 (9)
C1—C2—C3—C6	−173.9 (7)	C24—C25—C26—Br2	−177.1 (4)
C2—C3—C4—C5	−1.5 (13)	C25—C26—C27—C28	−1.8 (9)
C6—C3—C4—C5	175.2 (7)	Br2—C26—C27—C28	177.6 (4)
C1—N1—C5—C4	4.4 (10)	C24—C23—C28—C27	1.9 (8)
Cd1—N1—C5—C4	−172.8 (6)	C22—C23—C28—C27	−178.0 (5)
C3—C4—C5—N1	−2.1 (13)	C26—C27—C28—C23	−0.4 (8)
C2—C3—C6—C7	57.5 (14)

Symmetry code: (i) y, x, −z+1.

Experimental details

Crystal data
Chemical formula	[Cd₂(C₇H₄BrO₂)₄(C₁₃H₁₄N₂)₂]
M_r	1421.35
Crystal system, space group	Tetragonal, P4₃2₁2
Temperature (K)	223
a, c (Å)	13.7829 (10), 27.8235 (17)
V (Å³)	5285.6 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.89
Crystal size (mm)	0.45 × 0.40 × 0.35

Data collection
Diffractometer	Rigaku Mercury area-detector diffractometer
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.174, 0.256
No. of measured, independent and observed [I > 2σ(I)] reflections	25017, 6020, 5452
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.104, 1.05
No. of reflections	6020
No. of parameters	334
No. of restraints	34
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.71
Absolute structure	Flack (1983), 2533 Friedel pairs
Absolute structure parameter	0.006 (12)

Computer programs: CrystalClear (Rigaku, 2001), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

This work was supported by the Research Start-Up Fund for New Staff of Huaibei Normal University (600581) and the University of Malaya.

References

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