Di-μ-bromido-bis­[bromido(4,7-diphenyl-1,10-phenanthroline-κ2N,N′)cadmium]

Shirvan, S.A.; Haydari Dezfuli, S.; Khazali, F.; Aghajeri, M.; Borsalani, A.

doi:10.1107/S1600536812045928

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1471

doi:10.1107/S1600536812045928

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Di-μ-bromido-bis[bromido(4,7-diphenyl-1,10-phenanthroline-κ²N,N′)cadmium]

Sadif A. Shirvan,^a ^* Sara Haydari Dezfuli,^a Fereydoon Khazali,^a Manouchehr Aghajeri ^a and Ali Borsalani ^b

^aDepartment of Chemistry, Omidieh Branch, Islamic Azad University, Omidieh, Iran, and ^bDepartment of Petroleum Engineering, Omidieh Branch, Islamic Azad University, Omidieh, Iran
^*Correspondence e-mail: sadifchemist@hotmail.com

(Received 26 October 2012; accepted 7 November 2012; online 10 November 2012)

The title compound, [Cd₂Br₄(C₂₄H₁₆N₂)₂], consists of a centrosymmetric dimeric unit in which two Br atoms bridge two Cd^II atoms, forming a four-membered ring. A terminal Br atom and a bidentate chelating 4,7-diphenyl-1,10-phenanthroline ligand complete a square-pyramidal geometry for the Cd^II atom. In the crystal, C—H⋯Br hydrogen bonds and π–π contacts between the pyridine and phenyl rings [centroid–centroid distances = 3.704 (4) and 3.715 (4) Å] lead to a three-dimensional supramolecular structure.

Related literature

For related structures, see: Abedi et al. (2012 ); Ahmadi et al. (2008 ); Alizadeh et al. (2010 ); Chesnut et al. (2001 ); Gaballa et al. (2003 ); Yousefi et al. (2008 ).

Experimental

Crystal data

[Cd₂Br₄(C₂₄H₁₆N₂)₂]
M_r = 1209.20
Monoclinic, P 2₁ /n
a = 10.1704 (4) Å
b = 12.4702 (5) Å
c = 17.3444 (7) Å
β = 103.187 (3)°
V = 2141.73 (15) Å³
Z = 2
Mo Kα radiation
μ = 4.76 mm⁻¹
T = 120 K
0.25 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.385, T_max = 0.502
12072 measured reflections
4200 independent reflections
3248 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.129
S = 1.05
4200 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 1.15 e Å⁻³
Δρ_min = −1.05 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—N1	2.336 (6)
Cd1—N2	2.349 (6)
Cd1—Br1	2.5537 (9)
Cd1—Br2	2.6653 (8)
Cd1—Br2ⁱ	2.7518 (9)
Symmetry code: (i) -x, -y+2, -z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br2ⁱ	0.93	2.90	3.554 (7)	129
C21—H21⋯Br1ⁱⁱ	0.93	2.79	3.582 (8)	144
Symmetry codes: (i) -x, -y+2, -z; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812045928/hy2601sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812045928/hy2601Isup2.hkl

checkCIF report

Comment top

4,7-Diphenyl-1,10-phenanthroline (Ph₂phen) is a good bidentate ligand, and numerous complexes with Ph₂phen have been prepared, such as that of mercury (Alizadeh et al., 2010; Yousefi et al., 2008), gold (Ahmadi et al., 2008), indium (Abedi et al., 2012), copper (Chesnut et al., 2001) and platinum (Gaballa et al., 2003). Here, we report the synthesis and structure of the title compound.

The structure of the title compound (Fig. 1) consists of a centrosymmetric dimeric unit, [Cd₂Br₄(Ph₂phen)₂], in which two Br atoms bridge two Cd^II atoms, forming a four-membered ring; a terminal Br atom and a bidentate chelating Ph₂phen complete a five coordination (Table 1). In the crystal structure, intermolecular C—H···Br hydrogen bonds (Table 2) and π–π contacts (Fig. 2) between the pyridine and phenyl rings, Cg3···Cg4ⁱ and Cg6···Cg6ⁱ [symmetry code: (i) 1-x, 2-y, -z, Cg3, Cg4 and Cg6 are the centroids of the rings N1/C1–C3/C10/C24, N2/C13–C14/C21–C23 and C10–C13/C23–C24, respectively], with centroid–centroid distances of 3.704 (4) and 3.715 (4) Å, stabilize the structure.

Related literature top

For related structures, see: Abedi et al. (2012); Ahmadi et al. (2008); Alizadeh et al. (2010); Chesnut et al. (2001); Gaballa et al. (2003); Yousefi et al. (2008).

Experimental top

For the preparation of the title compound, a solution of Ph₂phen (0.44 g, 1.33 mmol) in methanol (10 ml) was added to a solution of CdBr₂.4H₂O (0.46 g, 1.33 mmol) in methanol (10 ml) at room temperature. Crystals suitable for X-ray diffraction experiment were obtained by methanol diffusion into a colorless solution in DMSO after one week (yield: 0.62 g, 77.1%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing diagram for the title compound. Hydrogen bonds are shown as dashed lines.

Di-µ-bromido-bis[bromido(4,7-diphenyl-1,10-phenanthroline- κ²N,N')cadmium] top

Crystal data top

[Cd₂Br₄(C₂₄H₁₆N₂)₂]	F(000) = 1168
M_r = 1209.20	D_x = 1.875 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 12072 reflections
a = 10.1704 (4) Å	θ = 2.4–26.0°
b = 12.4702 (5) Å	µ = 4.76 mm⁻¹
c = 17.3444 (7) Å	T = 120 K
β = 103.187 (3)°	Prism, colorless
V = 2141.73 (15) Å³	0.25 × 0.18 × 0.15 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	4200 independent reflections
Radiation source: fine-focus sealed tube	3248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→9
T_min = 0.385, T_max = 0.502	k = −15→15
12072 measured reflections	l = −21→21

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0692P)²] where P = (F_o² + 2F_c²)/3
4200 reflections	(Δ/σ)_max = 0.005
262 parameters	Δρ_max = 1.15 e Å⁻³
0 restraints	Δρ_min = −1.05 e Å⁻³

Crystal data top

[Cd₂Br₄(C₂₄H₁₆N₂)₂]	V = 2141.73 (15) Å³
M_r = 1209.20	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1704 (4) Å	µ = 4.76 mm⁻¹
b = 12.4702 (5) Å	T = 120 K
c = 17.3444 (7) Å	0.25 × 0.18 × 0.15 mm
β = 103.187 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4200 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3248 reflections with I > 2σ(I)
T_min = 0.385, T_max = 0.502	R_int = 0.090
12072 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	Δρ_max = 1.15 e Å⁻³
4200 reflections	Δρ_min = −1.05 e Å⁻³
262 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
C1	0.3033 (7)	0.7552 (6)	0.0038 (4)	0.0220 (15)
H1	0.2143	0.7327	−0.0137	0.026*
C2	0.4054 (7)	0.6893 (6)	−0.0089 (4)	0.0212 (15)
H2	0.3842	0.6233	−0.0336	0.025*
C3	0.5378 (7)	0.7205 (5)	0.0147 (4)	0.0198 (14)
C4	0.6478 (8)	0.6468 (5)	0.0047 (5)	0.0230 (15)
C5	0.6445 (9)	0.6043 (6)	−0.0702 (5)	0.0342 (19)
H5	0.5770	0.6250	−0.1134	0.041*
C6	0.7429 (9)	0.5306 (7)	−0.0800 (6)	0.044 (2)
H6	0.7435	0.5048	−0.1302	0.052*
C7	0.8396 (9)	0.4960 (6)	−0.0150 (6)	0.039 (2)
H7	0.9039	0.4457	−0.0212	0.047*
C8	0.8401 (8)	0.5363 (7)	0.0590 (6)	0.0329 (18)
H8	0.9037	0.5117	0.1028	0.040*
C9	0.7462 (8)	0.6139 (6)	0.0690 (5)	0.0281 (17)
H9	0.7500	0.6432	0.1187	0.034*
C10	0.5663 (7)	0.8236 (5)	0.0511 (4)	0.0171 (14)
C11	0.6978 (8)	0.8691 (6)	0.0725 (4)	0.0206 (15)
H11	0.7700	0.8317	0.0608	0.025*
C12	0.7213 (7)	0.9657 (6)	0.1095 (4)	0.0187 (14)
H12	0.8079	0.9947	0.1206	0.022*
C13	0.6142 (7)	1.0227 (5)	0.1312 (4)	0.0163 (13)
C14	0.6353 (8)	1.1181 (6)	0.1777 (4)	0.0226 (15)
C15	0.7704 (7)	1.1668 (5)	0.2081 (4)	0.0195 (14)
C16	0.8805 (9)	1.1070 (6)	0.2449 (4)	0.0303 (18)
H16	0.8708	1.0338	0.2523	0.036*
C17	1.0068 (8)	1.1553 (7)	0.2711 (5)	0.0318 (19)
H17	1.0812	1.1140	0.2948	0.038*
C18	1.0212 (9)	1.2650 (7)	0.2618 (5)	0.037 (2)
H18	1.1052	1.2975	0.2789	0.045*
C19	0.9106 (9)	1.3248 (7)	0.2272 (4)	0.0301 (18)
H19	0.9203	1.3982	0.2204	0.036*
C20	0.7865 (7)	1.2787 (6)	0.2025 (4)	0.0229 (15)
H20	0.7118	1.3214	0.1817	0.027*
C21	0.5205 (8)	1.1675 (6)	0.1945 (5)	0.0261 (16)
H21	0.5298	1.2292	0.2254	0.031*
C22	0.3948 (7)	1.1245 (6)	0.1654 (4)	0.0236 (16)
H22	0.3213	1.1601	0.1770	0.028*
C23	0.4797 (7)	0.9847 (5)	0.1065 (4)	0.0159 (13)
C24	0.4563 (7)	0.8838 (5)	0.0639 (4)	0.0172 (14)
N1	0.3274 (6)	0.8502 (5)	0.0403 (3)	0.0190 (12)
N2	0.3701 (6)	1.0356 (5)	0.1218 (3)	0.0197 (12)
Cd1	0.15894 (5)	0.95338 (4)	0.07604 (3)	0.01781 (15)
Br1	0.10996 (9)	0.87751 (7)	0.20336 (5)	0.0309 (2)
Br2	0.03037 (7)	1.14002 (5)	0.04404 (4)	0.02161 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.020 (4)	0.023 (4)	0.026 (4)	−0.002 (3)	0.011 (3)	0.000 (3)
C2	0.019 (3)	0.024 (4)	0.024 (3)	−0.001 (3)	0.012 (3)	−0.008 (3)
C3	0.025 (4)	0.016 (3)	0.018 (3)	0.000 (3)	0.005 (3)	0.003 (3)
C4	0.024 (4)	0.015 (3)	0.032 (4)	−0.004 (3)	0.011 (3)	−0.004 (3)
C5	0.040 (5)	0.024 (4)	0.038 (5)	−0.004 (4)	0.010 (4)	−0.012 (4)
C6	0.038 (5)	0.033 (5)	0.062 (6)	−0.001 (4)	0.017 (4)	−0.022 (4)
C7	0.031 (4)	0.018 (4)	0.079 (7)	−0.002 (3)	0.037 (5)	−0.012 (4)
C8	0.016 (3)	0.031 (4)	0.055 (5)	0.001 (3)	0.017 (3)	0.008 (4)
C9	0.026 (4)	0.025 (4)	0.040 (4)	0.002 (3)	0.023 (4)	0.002 (3)
C10	0.019 (3)	0.016 (3)	0.016 (3)	0.002 (3)	0.004 (3)	0.001 (3)
C11	0.027 (4)	0.022 (3)	0.015 (3)	0.002 (3)	0.010 (3)	−0.003 (3)
C12	0.018 (3)	0.021 (3)	0.016 (3)	−0.005 (3)	0.003 (3)	0.001 (3)
C13	0.017 (3)	0.021 (3)	0.015 (3)	0.002 (3)	0.012 (3)	0.004 (3)
C14	0.027 (4)	0.017 (3)	0.022 (3)	−0.002 (3)	0.001 (3)	−0.002 (3)
C15	0.026 (4)	0.017 (3)	0.017 (3)	0.001 (3)	0.007 (3)	−0.004 (3)
C16	0.044 (5)	0.026 (4)	0.018 (4)	0.002 (4)	0.002 (3)	−0.005 (3)
C17	0.024 (4)	0.047 (5)	0.023 (4)	0.006 (4)	0.002 (3)	−0.016 (4)
C18	0.034 (5)	0.046 (5)	0.034 (4)	−0.016 (4)	0.014 (4)	−0.024 (4)
C19	0.038 (5)	0.032 (4)	0.023 (4)	−0.010 (4)	0.011 (3)	−0.008 (3)
C20	0.023 (4)	0.025 (4)	0.022 (3)	0.002 (3)	0.008 (3)	−0.006 (3)
C21	0.024 (4)	0.021 (4)	0.033 (4)	0.006 (3)	0.006 (3)	−0.008 (3)
C22	0.020 (4)	0.026 (4)	0.031 (4)	0.006 (3)	0.020 (3)	−0.001 (3)
C23	0.020 (3)	0.016 (3)	0.013 (3)	0.001 (3)	0.007 (3)	0.002 (2)
C24	0.023 (4)	0.014 (3)	0.013 (3)	0.001 (3)	0.002 (3)	0.001 (3)
N1	0.018 (3)	0.022 (3)	0.019 (3)	−0.002 (2)	0.007 (2)	0.001 (2)
N2	0.019 (3)	0.023 (3)	0.023 (3)	0.005 (3)	0.016 (2)	0.003 (3)
Cd1	0.0164 (3)	0.0199 (3)	0.0193 (2)	0.0026 (2)	0.00858 (18)	0.0045 (2)
Br1	0.0369 (4)	0.0325 (4)	0.0291 (4)	0.0053 (3)	0.0195 (3)	0.0146 (3)
Br2	0.0191 (3)	0.0189 (3)	0.0267 (4)	0.0035 (3)	0.0050 (3)	0.0001 (3)

Geometric parameters (Å, º) top

C1—N1	1.339 (9)	C14—C21	1.409 (11)
C1—C2	1.381 (10)	C14—C15	1.484 (10)
C1—H1	0.9300	C15—C16	1.375 (11)
C2—C3	1.372 (10)	C15—C20	1.411 (10)
C2—H2	0.9300	C16—C17	1.398 (12)
C3—C10	1.432 (9)	C16—H16	0.9300
C3—C4	1.489 (10)	C17—C18	1.389 (13)
C4—C9	1.379 (11)	C17—H17	0.9300
C4—C5	1.396 (11)	C18—C19	1.369 (13)
C5—C6	1.398 (12)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.365 (11)
C6—C7	1.385 (14)	C19—H19	0.9300
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.377 (13)	C21—C22	1.371 (11)
C7—H7	0.9300	C21—H21	0.9300
C8—C9	1.398 (11)	C22—N2	1.333 (9)
C8—H8	0.9300	C22—H22	0.9300
C9—H9	0.9300	C23—N2	1.361 (9)
C10—C24	1.406 (10)	C23—C24	1.452 (9)
C10—C11	1.423 (10)	C24—N1	1.349 (9)
C11—C12	1.361 (9)	Cd1—N1	2.336 (6)
C11—H11	0.9300	Cd1—N2	2.349 (6)
C12—C13	1.421 (10)	Cd1—Br1	2.5537 (9)
C12—H12	0.9300	Cd1—Br2	2.6653 (8)
C13—C23	1.418 (9)	Cd1—Br2ⁱ	2.7518 (9)
C13—C14	1.426 (9)

N1—C1—C2	122.6 (7)	C15—C16—C17	120.5 (8)
N1—C1—H1	118.7	C15—C16—H16	119.8
C2—C1—H1	118.7	C17—C16—H16	119.8
C3—C2—C1	120.4 (7)	C18—C17—C16	120.1 (8)
C3—C2—H2	119.8	C18—C17—H17	120.0
C1—C2—H2	119.8	C16—C17—H17	120.0
C2—C3—C10	118.2 (7)	C19—C18—C17	119.3 (8)
C2—C3—C4	120.2 (6)	C19—C18—H18	120.4
C10—C3—C4	121.6 (6)	C17—C18—H18	120.4
C9—C4—C5	119.9 (7)	C20—C19—C18	121.1 (8)
C9—C4—C3	121.0 (7)	C20—C19—H19	119.4
C5—C4—C3	118.9 (7)	C18—C19—H19	119.4
C4—C5—C6	119.8 (8)	C19—C20—C15	120.6 (7)
C4—C5—H5	120.1	C19—C20—H20	119.7
C6—C5—H5	120.1	C15—C20—H20	119.7
C7—C6—C5	120.0 (9)	C22—C21—C14	120.0 (7)
C7—C6—H6	120.0	C22—C21—H21	120.0
C5—C6—H6	120.0	C14—C21—H21	120.0
C8—C7—C6	119.8 (8)	N2—C22—C21	125.0 (7)
C8—C7—H7	120.1	N2—C22—H22	117.5
C6—C7—H7	120.1	C21—C22—H22	117.5
C7—C8—C9	120.7 (8)	N2—C23—C13	124.2 (6)
C7—C8—H8	119.7	N2—C23—C24	117.2 (6)
C9—C8—H8	119.7	C13—C23—C24	118.6 (6)
C4—C9—C8	119.7 (8)	N1—C24—C10	122.7 (6)
C4—C9—H9	120.1	N1—C24—C23	117.3 (6)
C8—C9—H9	120.1	C10—C24—C23	120.0 (6)
C24—C10—C11	118.7 (6)	C1—N1—C24	118.6 (6)
C24—C10—C3	117.4 (6)	C1—N1—Cd1	123.1 (5)
C11—C10—C3	123.8 (7)	C24—N1—Cd1	118.0 (4)
C12—C11—C10	122.0 (7)	C22—N2—C23	116.2 (6)
C12—C11—H11	119.0	C22—N2—Cd1	126.5 (5)
C10—C11—H11	119.0	C23—N2—Cd1	117.2 (4)
C11—C12—C13	120.4 (6)	N1—Cd1—N2	70.2 (2)
C11—C12—H12	119.8	N1—Cd1—Br1	108.95 (14)
C13—C12—H12	119.8	N2—Cd1—Br1	102.32 (14)
C23—C13—C12	119.8 (6)	N1—Cd1—Br2	141.29 (14)
C23—C13—C14	117.4 (6)	N2—Cd1—Br2	93.23 (14)
C12—C13—C14	122.8 (6)	Br1—Cd1—Br2	108.68 (3)
C21—C14—C13	117.2 (7)	N1—Cd1—Br2ⁱ	89.71 (14)
C21—C14—C15	119.5 (6)	N2—Cd1—Br2ⁱ	150.28 (14)
C13—C14—C15	123.3 (7)	Br1—Cd1—Br2ⁱ	104.89 (3)
C16—C15—C20	118.3 (7)	Br2—Cd1—Br2ⁱ	89.24 (3)
C16—C15—C14	122.2 (7)	Cd1—Br2—Cd1ⁱ	90.76 (3)
C20—C15—C14	119.5 (7)

N1—C1—C2—C3	−1.2 (11)	C14—C13—C23—N2	2.6 (10)
C1—C2—C3—C10	−1.3 (10)	C12—C13—C23—C24	4.2 (9)
C1—C2—C3—C4	176.8 (7)	C14—C13—C23—C24	−175.7 (6)
C2—C3—C4—C9	−120.8 (8)	C11—C10—C24—N1	175.1 (6)
C10—C3—C4—C9	57.2 (10)	C3—C10—C24—N1	−2.9 (10)
C2—C3—C4—C5	54.2 (10)	C11—C10—C24—C23	−7.1 (9)
C10—C3—C4—C5	−127.8 (8)	C3—C10—C24—C23	174.8 (6)
C9—C4—C5—C6	−1.6 (12)	N2—C23—C24—N1	2.3 (9)
C3—C4—C5—C6	−176.7 (7)	C13—C23—C24—N1	−179.2 (6)
C4—C5—C6—C7	3.1 (13)	N2—C23—C24—C10	−175.6 (6)
C5—C6—C7—C8	−1.5 (13)	C13—C23—C24—C10	2.9 (9)
C6—C7—C8—C9	−1.6 (12)	C2—C1—N1—C24	1.6 (10)
C5—C4—C9—C8	−1.5 (11)	C2—C1—N1—Cd1	−172.4 (5)
C3—C4—C9—C8	173.5 (7)	C10—C24—N1—C1	0.6 (10)
C7—C8—C9—C4	3.1 (11)	C23—C24—N1—C1	−177.3 (6)
C2—C3—C10—C24	3.2 (9)	C10—C24—N1—Cd1	174.8 (5)
C4—C3—C10—C24	−174.8 (6)	C23—C24—N1—Cd1	−3.0 (8)
C2—C3—C10—C11	−174.7 (7)	C21—C22—N2—C23	0.7 (10)
C4—C3—C10—C11	7.2 (10)	C21—C22—N2—Cd1	176.5 (6)
C24—C10—C11—C12	4.4 (10)	C13—C23—N2—C22	−2.6 (9)
C3—C10—C11—C12	−177.7 (6)	C24—C23—N2—C22	175.7 (6)
C10—C11—C12—C13	2.7 (10)	C13—C23—N2—Cd1	−178.8 (5)
C11—C12—C13—C23	−7.1 (9)	C24—C23—N2—Cd1	−0.5 (7)
C11—C12—C13—C14	172.8 (6)	C1—N1—Cd1—N2	176.0 (6)
C23—C13—C14—C21	−0.7 (9)	C24—N1—Cd1—N2	2.0 (5)
C12—C13—C14—C21	179.4 (7)	C1—N1—Cd1—Br1	79.3 (5)
C23—C13—C14—C15	179.6 (6)	C24—N1—Cd1—Br1	−94.7 (5)
C12—C13—C14—C15	−0.3 (10)	C1—N1—Cd1—Br2	−114.7 (5)
C21—C14—C15—C16	133.3 (8)	C24—N1—Cd1—Br2	71.2 (5)
C13—C14—C15—C16	−47.1 (11)	C1—N1—Cd1—Br2ⁱ	−26.3 (5)
C21—C14—C15—C20	−44.0 (10)	C24—N1—Cd1—Br2ⁱ	159.7 (5)
C13—C14—C15—C20	135.7 (7)	C22—N2—Cd1—N1	−176.5 (6)
C20—C15—C16—C17	−4.2 (11)	C23—N2—Cd1—N1	−0.7 (4)
C14—C15—C16—C17	178.5 (7)	C22—N2—Cd1—Br1	−70.6 (6)
C15—C16—C17—C18	1.5 (12)	C23—N2—Cd1—Br1	105.2 (4)
C16—C17—C18—C19	0.3 (12)	C22—N2—Cd1—Br2	39.3 (6)
C17—C18—C19—C20	0.6 (12)	C23—N2—Cd1—Br2	−144.9 (4)
C18—C19—C20—C15	−3.4 (11)	C22—N2—Cd1—Br2ⁱ	133.5 (5)
C16—C15—C20—C19	5.2 (11)	C23—N2—Cd1—Br2ⁱ	−50.7 (6)
C14—C15—C20—C19	−177.5 (7)	N1—Cd1—Br2—Cd1ⁱ	88.6 (2)
C13—C14—C21—C22	−1.0 (11)	N2—Cd1—Br2—Cd1ⁱ	150.36 (14)
C15—C14—C21—C22	178.7 (7)	Br1—Cd1—Br2—Cd1ⁱ	−105.47 (3)
C14—C21—C22—N2	1.1 (12)	Br2ⁱ—Cd1—Br2—Cd1ⁱ	0.0
C12—C13—C23—N2	−177.5 (6)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br2ⁱ	0.93	2.90	3.554 (7)	129
C21—H21···Br1ⁱⁱ	0.93	2.79	3.582 (8)	144

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd₂Br₄(C₂₄H₁₆N₂)₂]
M_r	1209.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	10.1704 (4), 12.4702 (5), 17.3444 (7)
β (°)	103.187 (3)
V (Å³)	2141.73 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	4.76
Crystal size (mm)	0.25 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.385, 0.502
No. of measured, independent and observed [I > 2σ(I)] reflections	12072, 4200, 3248
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.129, 1.05
No. of reflections	4200
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.15, −1.05

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2006).

Selected bond lengths (Å) top

Cd1—N1	2.336 (6)	Cd1—Br2	2.6653 (8)
Cd1—N2	2.349 (6)	Cd1—Br2ⁱ	2.7518 (9)
Cd1—Br1	2.5537 (9)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br2ⁱ	0.93	2.90	3.554 (7)	129
C21—H21···Br1ⁱⁱ	0.93	2.79	3.582 (8)	144

Symmetry codes: (i) −x, −y+2, −z; (ii) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

We are grateful to the Islamic Azad University, Omidieh Branch, for financial support.

References

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