Crystal structure of di­bromido­(N,N-di­methyl­formamide-κO){2-(1H-indol-3-yl)-N-[(quinolin-2-yl-κN)methyl­idene]ethanamine-κN}cadmium

Faizi, M.S.H.; Sharkina, N.O.; Davydenko, Y.M.

doi:10.1107/S2056989015000778

metal-organic compounds

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages m31-m32

doi:10.1107/S2056989015000778

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Crystal structure of dibromido(N,N-dimethylformamide-κO){2-(1H-indol-3-yl)-N-[(quinolin-2-yl-κN)methylidene]ethanamine-κN}cadmium

Md. Serajul Haque Faizi,^a Natalia O. Sharkina ^b ^* and Yuliya M. Davydenko ^b

^aDepartment of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP 208 016, India, and ^bNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01601 Kyiv, Ukraine
^*Correspondence e-mail: nsharkina@ukr.net

Edited by J. F. Gallagher, Dublin City University, Ireland (Received 15 December 2014; accepted 14 January 2015; online 21 January 2015)

In the mononuclear title complex, [CdBr₂(C₂₀H₁₇N₃)(C₃H₇NO)], synthesized from the quinoline-derived Schiff base 2-(1H-indol-3-yl)-N-(quinolin-2-ylmethylene)ethanamine (IQME), the coordination geometry around the Cd²⁺ atom is distorted trigonal bipyramidal, the axial positions being occupied by the quinoline N atom [Cd—N = 2.401 (3) Å] and one dimethylformamide O-atom donor [Cd—O = 2.399 (2) Å]. The equatorial plane is formed by the imine N atom [Cd—N = 2.293 (3) Å] and two bromides [Cd—Br = 2.5621 (8) and 2.5676 (8) Å], with the deviation of the Cd^II atom from the equatorial plane being 0.046 (1) Å. An intramolecular C—H⋯Br interaction occurs. In the crystal, N—H⋯Br interactions generate [101] chains.

Keywords: crystal structure; Cd^II complex with IQME; quinolinyl-containing Schiff base; N—H⋯Br interactions.

CCDC reference: 1043591

1. Related literature

For applications of quinolinyl-containing Schiff bases, see: Motswainyana et al. (2013 ); Das et al. (2013 ); Song et al. (2011 ); Jursic et al. (2002 ). The present work is part of an ongoing structural study of Schiff base–metal complexes, see: Faizi & Hussain (2014 ); Faizi & Sen (2014 ); Faizi et al. (2014 ); Moroz et al. (2012 ). For properties of d¹⁰ metal complexes, see: Henkel & Krebs (2004 ); Kimblin et al. (2000 ); Penkova et al. (2010 ). For related structures, see: Penkova et al. (2009 $[Penkova, L. V., Maci\,ag, A., Rybak-Akimova, E. V., Haukka, M., Pavlenko, V. A., Iskenderov, T. S., Kozłowski, H., Meyer, F. & Fritsky, I. O. (2009). Inorg. Chem. 48, 6960-6971.]$ ); Petrusenko et al. (1997 ).

2. Experimental

2.1. Crystal data

[CdBr₂(C₂₀H₁₇N₃)(C₃H₇NO)]
M_r = 644.68
Monoclinic, P 2₁ /n
a = 14.686 (4) Å
b = 8.384 (2) Å
c = 20.157 (6) Å
β = 97.785 (5)°
V = 2458.9 (12) Å³
Z = 4
Mo Kα radiation
μ = 4.16 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.12 mm

2.2. Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.490, T_max = 0.635
12172 measured reflections
4308 independent reflections
3120 reflections with I > 2σ(I)
R_int = 0.034

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.092
S = 1.02
4308 reflections
286 parameters
90 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N3⋯Br2ⁱ	0.94 (3)	2.65 (3)	3.504 (4)	153 (3)
C21—H21⋯Br1	0.93	2.83	3.527 (5)	132
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2001 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1043591

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015000778/gg2145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015000778/gg2145Isup2.hkl

checkCIF report

Comment top

Quinolyl derivatives of Schiff bases are important building blocks for many important compounds widely used in biological applications such as antioxidative, anticancer, fluorescent probe agents in industry, in coordination chemistry and in catalysis (Motswainyana et al. (2013); Das et al. (2013); Song et al. (2011); Jursic et al.(2002). Complexes of d¹⁰ metal ions such as Zn(II) and Cd(II) are of interest because of their fluorescent properties and involvement in many biological processes (Kimblin et al., 2000; Henkel & Krebs, 2004; Penkova et al., 2010). The synthesis of a complex of cadmium (II) using the quinoline aldehyde derivative of the Schiff base 2-(1H-indole-3-yl)-N-(quinolin-2-ylmethylene)ethanamine (IQME) has not previously been reported. The present work is part of an ongoing structural study of Schiff-base metal complexes (Faizi & Hussain, 2014; Faizi & Sen, 2014; Faizi et al. 2014; Moroz et al., 2012) and we report herein a newly synthesized structure of Cd^II complex with IQME, [Cd(Br)₂(C₂₀H₁₇N₃)(C₃H₇NO)].

In the structure of title compound, the geometry around the Cd centre can be described as a distorted trigonal bipyramidal, in which the Cd atom is surrounded by one bidentate ligand, two bromines and one DMF molecule coordinated via oxygen (Fig. 1). The axial positions are occupied by N_quinolyl of the chelate and O from the DMF molecule [O(1)-Cd(1)-N(1) 160.33 (17) Å], while the equatorial plane is formed by the N_imine atom and two bromides, with the deviation of the Cd centre from the equatorial plane of 0.040 Å. The axial plane and the equatorial plane make a dihedral angle of 89.42 Å. The Cd-N_imine bond (2.290 (4) Å) is significantly shorter than the Cd1-N_quinolyl bond (2.401 (4) Å), which can be attributed to the coordination of the DMF molecule. It is noteworthy that the quinoline ring and indole ring are not coplanar, having a dihedral angle of 35.01 Å. The C—N, C═N and C—C bond lenths are normal and close to the values observed in the related structures (Penkova et al., 2009; Petrusenko et al., 1997). Intermolecular N-H···Br and C-H···Br interactions generate an overall layered structure lying parallel to (010) (Fig. 2).

Related literature top

For applications of quinolinyl-containing Schiff bases see: Motswainyana et al. (2013); Das et al. (2013); Song et al. (2011); Jursic et al. (2002). The present work is part of an ongoing structural study of Schiff base–metal complexes, see: Faizi & Hussain (2014); Faizi & Sen (2014); Faizi et al. (2014); Moroz et al. (2012). For properties of d¹⁰ metal complexes, see: Henkel & Krebs (2004); Kimblin et al. (2000); Penkova et al. (2010). For related structures, see: Penkova et al. (2009); Petrusenko et al. (1997).

Experimental top

The iminoquinolyl compound 2-(1H-indole-3-yl)-N-(quinolin-2-ylmethylene)ethanamine (IQME) was prepared by reacting 2-quinolinecarboxaldehyde with a substituted aniline and was obtained in high yields. This compound was characterized by FT—IR, NMR and ESI-Mass spectroscopy. A mixture of IQME (0.10 g, 0.33 mmol), cadmium(II) bromide (0.09 g, 0.33 mmol) and ethanol (5 ml) were stirred vigorously for 1 h, after which the precipitate was filtered off and redissolved in dimethylformamide. Crystals of the title complex suitable for X-ray analysis was obtained within 3 days by slow evaporation of the DMF solvent.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 2015).

Figures top

	Fig. 1. The molecular conformation and atom-numbering scheme for the title compound, with non-H atoms drawn as 40% probability displacement ellipsoids.
	Fig. 2. The one-dimensional hydrogen-bonded chain structure in the title compound extending along b, with hydrogen bonds shown as dashed lines.

Dibromido(N,N-dimethylformamide-κO){2-(1H-indol-3-yl)-N-[(quinolin-2-yl-κN)methylidene]ethanamine-κN}cadmium top

Crystal data top

[CdBr₂(C₂₀H₁₇N₃)(C₃H₇NO)]	F(000) = 1264
M_r = 644.68	D_x = 1.741 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2146 reflections
a = 14.686 (4) Å	θ = 1.8–25.0°
b = 8.384 (2) Å	µ = 4.16 mm⁻¹
c = 20.157 (6) Å	T = 100 K
β = 97.785 (5)°	Block, yellow
V = 2458.9 (12) Å³	0.20 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	4308 independent reflections
Radiation source: fine-focus sealed tube	3120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
/w–scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −17→17
T_min = 0.490, T_max = 0.635	k = −9→9
12172 measured reflections	l = −20→23

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.046P)²] where P = (F_o² + 2F_c²)/3
4308 reflections	(Δ/σ)_max = 0.001
286 parameters	Δρ_max = 0.74 e Å⁻³
90 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[CdBr₂(C₂₀H₁₇N₃)(C₃H₇NO)]	V = 2458.9 (12) Å³
M_r = 644.68	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.686 (4) Å	µ = 4.16 mm⁻¹
b = 8.384 (2) Å	T = 100 K
c = 20.157 (6) Å	0.20 × 0.15 × 0.12 mm
β = 97.785 (5)°

Data collection top

Bruker SMART APEX CCD diffractometer	4308 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	3120 reflections with I > 2σ(I)
T_min = 0.490, T_max = 0.635	R_int = 0.034
12172 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	90 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.74 e Å⁻³
4308 reflections	Δρ_min = −0.47 e Å⁻³
286 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.5561 (3)	0.7787 (5)	0.6436 (2)	0.0453 (10)
C2	0.5466 (3)	0.7981 (6)	0.5739 (2)	0.0566 (12)
H2	0.5985	0.7951	0.5520	0.068*
C3	0.4627 (4)	0.8211 (6)	0.5382 (3)	0.0677 (14)
H3	0.4574	0.8341	0.4920	0.081*
C4	0.3834 (3)	0.8255 (6)	0.5702 (3)	0.0700 (15)
H4	0.3263	0.8418	0.5450	0.084*
C5	0.3891 (3)	0.8065 (6)	0.6373 (3)	0.0649 (13)
H5	0.3359	0.8083	0.6577	0.078*
C6	0.4762 (3)	0.7837 (5)	0.6770 (2)	0.0502 (11)
C7	0.4882 (3)	0.7673 (6)	0.7461 (3)	0.0577 (12)
H7	0.4372	0.7704	0.7689	0.069*
C8	0.5739 (3)	0.7469 (6)	0.7813 (2)	0.0554 (12)
H8	0.5820	0.7370	0.8277	0.067*
C9	0.6492 (3)	0.7413 (5)	0.7455 (2)	0.0439 (10)
C10	0.7428 (3)	0.7150 (5)	0.7806 (2)	0.0441 (10)
H10	0.7511	0.7098	0.8272	0.053*
C11	0.9037 (3)	0.6785 (5)	0.7898 (2)	0.0469 (11)
H11A	0.9358	0.5919	0.7711	0.056*
H11B	0.8962	0.6500	0.8354	0.056*
C12	0.9611 (3)	0.8304 (5)	0.7905 (2)	0.0522 (11)
H12A	0.9698	0.8576	0.7450	0.063*
H12B	0.9284	0.9176	0.8084	0.063*
C13	1.0533 (3)	0.8096 (5)	0.8323 (2)	0.0495 (11)
C14	1.0778 (4)	0.8648 (6)	0.8953 (2)	0.0636 (13)
H14	1.0406	0.9277	0.9185	0.076*
C15	1.1988 (3)	0.7273 (6)	0.8722 (2)	0.0556 (12)
C16	1.2826 (3)	0.6473 (7)	0.8738 (3)	0.0686 (14)
H16	1.3262	0.6495	0.9118	0.082*
C17	1.2980 (4)	0.5663 (7)	0.8180 (3)	0.0753 (15)
H17	1.3532	0.5119	0.8182	0.090*
C18	1.2341 (4)	0.5622 (7)	0.7609 (3)	0.0715 (15)
H18	1.2477	0.5079	0.7232	0.086*
C19	1.1504 (3)	0.6380 (6)	0.7594 (2)	0.0583 (12)
H19	1.1074	0.6339	0.7211	0.070*
C20	1.1309 (3)	0.7205 (5)	0.8157 (2)	0.0477 (10)
C21	0.9869 (3)	0.7038 (7)	0.5975 (3)	0.0697 (15)
H21	0.9706	0.8096	0.5887	0.084*
C22	1.1131 (5)	0.7539 (10)	0.5352 (5)	0.150 (4)
H22A	1.1142	0.7114	0.4911	0.225*
H22B	1.1747	0.7609	0.5580	0.225*
H22C	1.0859	0.8583	0.5319	0.225*
C23	1.0901 (5)	0.4887 (8)	0.5815 (3)	0.099 (2)
H23A	1.1049	0.4468	0.5399	0.149*
H23B	1.0420	0.4258	0.5962	0.149*
H23C	1.1436	0.4849	0.6146	0.149*
Cd1	0.78346 (2)	0.70754 (4)	0.635528 (15)	0.04782 (13)
N1	0.6416 (2)	0.7570 (4)	0.67886 (17)	0.0435 (8)
N2	0.8125 (2)	0.6993 (4)	0.75016 (17)	0.0426 (8)
N3	1.1651 (3)	0.8157 (6)	0.9203 (2)	0.0696 (12)
N4	1.0598 (3)	0.6510 (6)	0.5720 (2)	0.0701 (12)
Br1	0.79839 (4)	0.96756 (6)	0.57108 (3)	0.06928 (18)
Br2	0.72209 (4)	0.46231 (6)	0.56734 (2)	0.06947 (18)
O1	0.9397 (2)	0.6298 (5)	0.63075 (17)	0.0739 (10)
H3N3	1.192 (3)	0.842 (5)	0.9637 (13)	0.071 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.045 (2)	0.041 (3)	0.050 (3)	−0.002 (2)	0.0079 (19)	−0.004 (2)
C2	0.051 (3)	0.067 (3)	0.050 (3)	0.002 (3)	0.003 (2)	−0.002 (2)
C3	0.066 (3)	0.073 (4)	0.060 (3)	0.001 (3)	−0.006 (2)	0.000 (3)
C4	0.044 (3)	0.076 (4)	0.083 (4)	0.009 (3)	−0.013 (3)	−0.005 (3)
C5	0.043 (3)	0.070 (4)	0.081 (3)	0.005 (3)	0.008 (2)	−0.011 (3)
C6	0.043 (2)	0.043 (3)	0.066 (3)	0.000 (2)	0.012 (2)	−0.007 (2)
C7	0.053 (3)	0.058 (3)	0.066 (3)	0.001 (2)	0.022 (2)	−0.007 (2)
C8	0.058 (3)	0.061 (3)	0.051 (3)	0.002 (2)	0.020 (2)	−0.003 (2)
C9	0.048 (2)	0.040 (3)	0.045 (3)	0.001 (2)	0.0099 (19)	−0.0047 (19)
C10	0.056 (2)	0.041 (3)	0.037 (2)	0.002 (2)	0.0097 (19)	−0.0008 (19)
C11	0.051 (2)	0.046 (3)	0.042 (2)	0.001 (2)	0.001 (2)	0.004 (2)
C12	0.056 (3)	0.046 (3)	0.054 (3)	0.001 (2)	0.005 (2)	0.003 (2)
C13	0.056 (3)	0.047 (3)	0.044 (3)	−0.010 (2)	0.004 (2)	0.001 (2)
C14	0.070 (3)	0.065 (3)	0.057 (3)	−0.012 (3)	0.011 (2)	−0.014 (3)
C15	0.051 (3)	0.064 (3)	0.050 (3)	−0.014 (2)	−0.003 (2)	0.009 (2)
C16	0.056 (3)	0.075 (4)	0.071 (3)	−0.010 (3)	−0.006 (3)	0.020 (3)
C17	0.051 (3)	0.080 (4)	0.094 (4)	−0.004 (3)	0.006 (3)	0.016 (3)
C18	0.067 (3)	0.081 (4)	0.071 (3)	−0.003 (3)	0.025 (3)	0.001 (3)
C19	0.064 (3)	0.068 (3)	0.042 (3)	−0.003 (3)	0.004 (2)	0.004 (2)
C20	0.054 (2)	0.049 (3)	0.040 (2)	−0.009 (2)	0.0054 (19)	0.005 (2)
C21	0.057 (3)	0.090 (4)	0.064 (3)	0.002 (3)	0.017 (3)	0.007 (3)
C22	0.126 (7)	0.142 (7)	0.208 (10)	−0.025 (5)	0.113 (7)	0.009 (6)
C23	0.094 (5)	0.116 (5)	0.089 (4)	0.031 (4)	0.020 (4)	−0.009 (4)
Cd1	0.0476 (2)	0.0570 (2)	0.0402 (2)	0.00472 (16)	0.01071 (14)	0.00239 (15)
N1	0.0435 (19)	0.048 (2)	0.040 (2)	0.0015 (17)	0.0078 (15)	−0.0050 (16)
N2	0.0440 (19)	0.042 (2)	0.0394 (19)	0.0019 (17)	−0.0016 (15)	0.0021 (16)
N3	0.072 (3)	0.089 (4)	0.045 (3)	−0.016 (2)	−0.005 (2)	−0.009 (2)
N4	0.053 (2)	0.092 (3)	0.070 (3)	0.001 (2)	0.025 (2)	−0.005 (2)
Br1	0.0819 (4)	0.0595 (3)	0.0678 (4)	0.0028 (3)	0.0150 (3)	0.0150 (3)
Br2	0.1018 (4)	0.0537 (3)	0.0519 (3)	0.0022 (3)	0.0066 (3)	−0.0024 (2)
O1	0.0531 (19)	0.101 (3)	0.072 (2)	0.0162 (19)	0.0258 (17)	0.026 (2)

Geometric parameters (Å, º) top

C1—N1	1.369 (5)	C14—H14	0.9300
C1—C2	1.401 (6)	C15—N3	1.366 (6)
C1—C6	1.431 (6)	C15—C16	1.397 (7)
C2—C3	1.355 (6)	C15—C20	1.409 (6)
C2—H2	0.9300	C16—C17	1.360 (8)
C3—C4	1.407 (7)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.383 (7)
C4—C5	1.352 (7)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.381 (7)
C5—C6	1.427 (6)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.392 (6)
C6—C7	1.387 (7)	C19—H19	0.9300
C7—C8	1.370 (6)	C21—O1	1.201 (5)
C7—H7	0.9300	C21—N4	1.324 (6)
C8—C9	1.400 (6)	C21—H21	0.9300
C8—H8	0.9300	C22—N4	1.437 (8)
C9—N1	1.338 (5)	C22—H22A	0.9600
C9—C10	1.476 (6)	C22—H22B	0.9600
C10—N2	1.270 (5)	C22—H22C	0.9600
C10—H10	0.9300	C23—N4	1.437 (7)
C11—N2	1.474 (5)	C23—H23A	0.9600
C11—C12	1.526 (6)	C23—H23B	0.9600
C11—H11A	0.9700	C23—H23C	0.9600
C11—H11B	0.9700	Cd1—N2	2.293 (3)
C12—C13	1.505 (6)	Cd1—O1	2.399 (3)
C12—H12A	0.9700	Cd1—N1	2.401 (3)
C12—H12B	0.9700	Cd1—Br1	2.5621 (8)
C13—C14	1.353 (6)	Cd1—Br2	2.5676 (8)
C13—C20	1.439 (6)	N3—H3N3	0.937 (19)
C14—N3	1.376 (7)

N1—C1—C2	119.7 (4)	C17—C16—H16	121.1
N1—C1—C6	120.8 (4)	C15—C16—H16	121.1
C2—C1—C6	119.5 (4)	C16—C17—C18	122.0 (5)
C3—C2—C1	120.6 (5)	C16—C17—H17	119.0
C3—C2—H2	119.7	C18—C17—H17	119.0
C1—C2—H2	119.7	C19—C18—C17	120.6 (5)
C2—C3—C4	120.6 (5)	C19—C18—H18	119.7
C2—C3—H3	119.7	C17—C18—H18	119.7
C4—C3—H3	119.7	C18—C19—C20	119.5 (5)
C5—C4—C3	120.9 (5)	C18—C19—H19	120.3
C5—C4—H4	119.6	C20—C19—H19	120.3
C3—C4—H4	119.6	C19—C20—C15	118.5 (4)
C4—C5—C6	120.4 (5)	C19—C20—C13	134.8 (4)
C4—C5—H5	119.8	C15—C20—C13	106.7 (4)
C6—C5—H5	119.8	O1—C21—N4	127.1 (6)
C7—C6—C5	123.9 (4)	O1—C21—H21	116.5
C7—C6—C1	118.0 (4)	N4—C21—H21	116.5
C5—C6—C1	118.0 (4)	N4—C22—H22A	109.5
C8—C7—C6	120.9 (4)	N4—C22—H22B	109.5
C8—C7—H7	119.5	H22A—C22—H22B	109.5
C6—C7—H7	119.5	N4—C22—H22C	109.5
C7—C8—C9	118.2 (4)	H22A—C22—H22C	109.5
C7—C8—H8	120.9	H22B—C22—H22C	109.5
C9—C8—H8	120.9	N4—C23—H23A	109.5
N1—C9—C8	123.4 (4)	N4—C23—H23B	109.5
N1—C9—C10	116.2 (4)	H23A—C23—H23B	109.5
C8—C9—C10	120.4 (4)	N4—C23—H23C	109.5
N2—C10—C9	122.9 (4)	H23A—C23—H23C	109.5
N2—C10—H10	118.6	H23B—C23—H23C	109.5
C9—C10—H10	118.6	N2—Cd1—O1	89.09 (12)
N2—C11—C12	111.5 (3)	N2—Cd1—N1	71.98 (12)
N2—C11—H11A	109.3	O1—Cd1—N1	160.51 (12)
C12—C11—H11A	109.3	N2—Cd1—Br1	121.29 (9)
N2—C11—H11B	109.3	O1—Cd1—Br1	93.61 (9)
C12—C11—H11B	109.3	N1—Cd1—Br1	100.11 (9)
H11A—C11—H11B	108.0	N2—Cd1—Br2	121.28 (9)
C13—C12—C11	111.2 (3)	O1—Cd1—Br2	91.67 (10)
C13—C12—H12A	109.4	N1—Cd1—Br2	94.25 (8)
C11—C12—H12A	109.4	Br1—Cd1—Br2	117.24 (3)
C13—C12—H12B	109.4	C9—N1—C1	118.7 (4)
C11—C12—H12B	109.4	C9—N1—Cd1	112.9 (3)
H12A—C12—H12B	108.0	C1—N1—Cd1	127.9 (3)
C14—C13—C20	106.1 (4)	C10—N2—C11	118.9 (4)
C14—C13—C12	126.2 (5)	C10—N2—Cd1	115.6 (3)
C20—C13—C12	127.6 (4)	C11—N2—Cd1	125.5 (3)
C13—C14—N3	111.0 (5)	C15—N3—C14	108.2 (4)
C13—C14—H14	124.5	C15—N3—H3N3	130 (3)
N3—C14—H14	124.5	C14—N3—H3N3	122 (3)
N3—C15—C16	130.3 (5)	C21—N4—C23	121.1 (5)
N3—C15—C20	108.1 (4)	C21—N4—C22	121.7 (6)
C16—C15—C20	121.6 (5)	C23—N4—C22	117.2 (5)
C17—C16—C15	117.7 (5)	C21—O1—Cd1	120.7 (3)

N1—C1—C2—C3	−179.4 (4)	C8—C9—N1—C1	−0.4 (6)
C6—C1—C2—C3	−0.1 (7)	C10—C9—N1—C1	178.9 (4)
C1—C2—C3—C4	−0.2 (8)	C8—C9—N1—Cd1	−172.7 (3)
C2—C3—C4—C5	−0.2 (8)	C10—C9—N1—Cd1	6.5 (5)
C3—C4—C5—C6	0.9 (8)	C2—C1—N1—C9	179.0 (4)
C4—C5—C6—C7	178.3 (5)	C6—C1—N1—C9	−0.4 (6)
C4—C5—C6—C1	−1.1 (7)	C2—C1—N1—Cd1	−10.0 (6)
N1—C1—C6—C7	0.6 (6)	C6—C1—N1—Cd1	170.7 (3)
C2—C1—C6—C7	−178.7 (4)	N2—Cd1—N1—C9	−5.4 (3)
N1—C1—C6—C5	−179.9 (4)	O1—Cd1—N1—C9	8.8 (6)
C2—C1—C6—C5	0.7 (7)	Br1—Cd1—N1—C9	−125.2 (3)
C5—C6—C7—C8	−179.5 (5)	Br2—Cd1—N1—C9	116.1 (3)
C1—C6—C7—C8	−0.1 (7)	N2—Cd1—N1—C1	−176.9 (4)
C6—C7—C8—C9	−0.6 (7)	O1—Cd1—N1—C1	−162.6 (4)
C7—C8—C9—N1	0.9 (7)	Br1—Cd1—N1—C1	63.3 (3)
C7—C8—C9—C10	−178.3 (4)	Br2—Cd1—N1—C1	−55.3 (3)
N1—C9—C10—N2	−3.7 (6)	C9—C10—N2—C11	178.1 (4)
C8—C9—C10—N2	175.6 (4)	C9—C10—N2—Cd1	−1.6 (5)
N2—C11—C12—C13	178.7 (4)	C12—C11—N2—C10	−105.1 (4)
C11—C12—C13—C14	−102.0 (5)	C12—C11—N2—Cd1	74.5 (4)
C11—C12—C13—C20	74.1 (6)	O1—Cd1—N2—C10	−171.7 (3)
C20—C13—C14—N3	−0.7 (6)	N1—Cd1—N2—C10	3.6 (3)
C12—C13—C14—N3	176.0 (4)	Br1—Cd1—N2—C10	94.6 (3)
N3—C15—C16—C17	179.5 (5)	Br2—Cd1—N2—C10	−80.3 (3)
C20—C15—C16—C17	2.1 (7)	O1—Cd1—N2—C11	8.6 (3)
C15—C16—C17—C18	0.3 (8)	N1—Cd1—N2—C11	−176.1 (3)
C16—C17—C18—C19	−1.7 (8)	Br1—Cd1—N2—C11	−85.0 (3)
C17—C18—C19—C20	0.7 (8)	Br2—Cd1—N2—C11	100.0 (3)
C18—C19—C20—C15	1.7 (7)	C16—C15—N3—C14	−177.8 (5)
C18—C19—C20—C13	−179.3 (5)	C20—C15—N3—C14	−0.2 (5)
N3—C15—C20—C19	179.0 (4)	C13—C14—N3—C15	0.6 (6)
C16—C15—C20—C19	−3.1 (7)	O1—C21—N4—C23	1.1 (9)
N3—C15—C20—C13	−0.2 (5)	O1—C21—N4—C22	−177.3 (7)
C16—C15—C20—C13	177.6 (4)	N4—C21—O1—Cd1	−155.8 (4)
C14—C13—C20—C19	−178.5 (5)	N2—Cd1—O1—C21	−129.2 (4)
C12—C13—C20—C19	4.8 (8)	N1—Cd1—O1—C21	−142.7 (4)
C14—C13—C20—C15	0.6 (5)	Br1—Cd1—O1—C21	−7.9 (4)
C12—C13—C20—C15	−176.1 (4)	Br2—Cd1—O1—C21	109.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N3···Br2ⁱ	0.94 (3)	2.65 (3)	3.504 (4)	153 (3)
C21—H21···Br1	0.93	2.83	3.527 (5)	132

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N3···Br2ⁱ	0.94 (3)	2.65 (3)	3.504 (4)	153 (3)
C21—H21···Br1	0.93	2.83	3.527 (5)	132

Symmetry code: (i) x+1/2, −y+3/2, z+1/2.

Acknowledgements

The authors are grateful to the Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, UP-208016, India for the data collection.

References

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Volume 71| Part 2| February 2015| Pages m31-m32

doi:10.1107/S2056989015000778

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

Crystal structure of di­bromido­(N,N-di­methyl­formamide-κO){2-(1H-indol-3-yl)-N-[(quinolin-2-yl-κN)methyl­­idene]ethanamine-κN}cadmium

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Crystal structure of dibromido(N,N-dimethylformamide-κO){2-(1H-indol-3-yl)-N-[(quinolin-2-yl-κN)methylidene]ethanamine-κN}cadmium