Bis(4-meth­oxy­benzyl­ammonium) tetra­bromido­cadmate(II)

Umarani, P.; Thiruvalluvar, A.A.; Ramachandra Raja, C.

doi:10.1107/S2414314618007952

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 6| June 2018| x180795

https://doi.org/10.1107/S2414314618007952

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Bis(4-methoxybenzylammonium) tetrabromidocadmate(II)

Parthasarathy Umarani,^a Aravazhi Amalan Thiruvalluvar ^b ^* and Chidambaram Ramachandra Raja ^a

^aDepartment of Physics, Government Arts College (Autonomous), Kumbakonam 612 002, Tamilnadu, India, and ^bPrincipal, Kunthavai Naacchiyaar Government Arts College for Women (Autonomous), Thanjavur 613 007, Tamilnadu, India
^*Correspondence e-mail: thiruvalluvar.a@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 28 May 2018; accepted 30 May 2018; online 5 June 2018)

The asymmetric unit of the organic–inorganic hybrid salt, (C₈H₁₂NO)₂[CdBr₄], consists of two 4-methoxybenzylammonium cations and one [CdBr₄]²⁻ anion. The cations and anions are connected by a complex series of N—H⋯Br and C—H⋯Br hydrogen bonds. No π–π stacking interactions occur between the benzene rings but two C—H⋯π interactions are observed.

Keywords: crystal structure; organic–inorganic hybrid material; hydrogen bonds; C—H⋯π interactions.

CCDC reference: 1814527

Structure description

Work on non-linear optical (NLO) crystals is an attractive field of interest in current research into applications of laser technology, optical data storage, optical communication, optical switching, optical signal processing, and optical power-limiting processes (Umarani et al., 2017 ; Mageshwari et al., 2016 ). Recently, researchers have concentrated on the design of new metal–organic NLO crystals. These materials enhance the desirable NLO response of organic crystals with the high thermal and mechanical properties of inorganic crystals. This new class of materials with remarkable properties are ideal for device fabrication. Incorporating transition metal ions such as Cd²⁺, Zn²⁺, Hg²⁺ with filled electron d shells into organic materials creates more energy sublevels and enhances the optical non-linearity through a charge-transfer mechanism (Yang et al., 2013 ).

As a part of a continuation of our research work on 4-methoxybenzylamine-based crystals, we report here the synthesis and crystal structure of the metal–organic title structure, bis(4-methoxybenzylammonium) tetrabromidocadmate(II). As the crystal belongs to the centrosymmetric monoclinic space group P2₁/n, it can be used in third-harmonic generation for a Nd:YAG laser at a wavelength of 1064 nm (Mageshwari et al., 2016).

The asymmetric unit of the the title compound consists of one tetrabromidocadmate anion, [CdBr₄]²⁻, and two 4-methoxybenzylammonium cations, (C₈H₁₂NO)⁺, as shown in Fig. 1. The cadmium cation coordination environment is distorted tetrahedral. The 4-methoxybenzylammonium cations are sandwiched between the tetrabromidocadmate layers (Fig. 2). The crystal packing is stabilized by a complex hydrogen-bonding system, involving the N—H bonds of the positively charged ammonium groups and, to a minor extent, the methylene group as donors, with the bromide ligands of the anions as acceptors (Table 1). The benzene rings of the cations are also linked by weak C—H⋯π interactions (Fig. 3, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Br2	0.97	3.10	3.822 (8)	133
C8—H8B⋯Br1ⁱ	0.97	2.98	3.846 (9)	150
N1—H1A⋯Br4ⁱⁱ	0.89	2.62	3.439 (7)	154
N1—H1B⋯Br3ⁱⁱⁱ	0.89	2.63	3.450 (7)	154
N1—H1C⋯Br3	0.89	2.67	3.418 (7)	142
N2—H2A⋯Br4	0.89	2.54	3.380 (8)	157
N2—H2B⋯Br1	0.89	2.64	3.446 (8)	152
N2—H2C⋯Br1^iv	0.89	3.13	3.651 (10)	119
N2—H2C⋯Br2^iv	0.89	2.67	3.377 (7)	137
C10—H10⋯Cg2^v	0.93	2.88	3.682 (9)	145
C14—H14⋯Cg1ⁱⁱ	0.93	2.82	3.621 (8)	146
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+2, -z+1; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
A view of the asymmetric unit of the title compound showing the atom numbering with displacement ellipsoids drawn at the 30% probability level. Dashed lines indicate hydrogen-bonding interactions.

Figure 2
Packing diagram of the title compound viewed along the b axis, showing the alternate stacking of the organic and inorganic layers. Dashed lines indicate hydrogen bonds.

Figure 3
A partial packing diagram showing the C—H⋯π interactions (details in Table 1

Synthesis and crystallization

20 mmol (2.74 g) of 4-methoxybenzylamine (Sigma Aldrich 98%), 20 mmol of aqueous hydrobromic acid (Merck 48%), and 10 mmol (2.72 g) of cadmium (II) bromide (Sigma Aldrich 98%) were mixed in 50 ml of water. The solution was stirred at room temperature for more than 3 h and was then set aside to allow slow evaporation. Transparent crystals suitable for single-crystal X-ray diffraction were collected after two weeks.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	(C₈H₁₂NO)₂[CdBr₄]
M_r	708.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	16.7564 (13), 7.9403 (6), 17.9303 (13)
β (°)	103.777 (3)
V (Å³)	2317.0 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	7.85
Crystal size (mm)	0.38 × 0.22 × 0.05

Data collection
Diffractometer	Bruker Kappa APEXII CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.11, 0.67
No. of measured, independent and observed [I > 2σ(I)] reflections	54597, 4087, 2873
R_int	0.151
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.123, 1.06
No. of reflections	4087
No. of parameters	231
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.67
Computer programs: APEX2 and SAINT (Bruker, 2009), SHELXT2018 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1814527

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618007952/sj4181sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618007952/sj4181Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618007952/sj4181Isup3.cdx

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Bis(4-methoxybenzylammonium) tetrabromidocadmate(II) top

Crystal data top

(C₈H₁₂NO)₂[CdBr₄]	F(000) = 1352
M_r = 708.41	D_x = 2.031 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 16.7564 (13) Å	Cell parameters from 8254 reflections
b = 7.9403 (6) Å	θ = 3.0–28.3°
c = 17.9303 (13) Å	µ = 7.85 mm⁻¹
β = 103.777 (3)°	T = 296 K
V = 2317.0 (3) Å³	Block, colourless
Z = 4	0.38 × 0.22 × 0.05 mm

Data collection top

Bruker Kappa APEXII CMOS diffractometer	2873 reflections with I > 2σ(I)
Radiation source: Sealed tube	R_int = 0.151
ω and φ scan	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.11, T_max = 0.67	k = −9→9
54597 measured reflections	l = −21→21
4087 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0616P)² + 2.4383P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.96 e Å⁻³
4087 reflections	Δρ_min = −0.67 e Å⁻³
231 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0028 (2)

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.

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

	x	y	z	U_iso*/U_eq
C1	0.3209 (5)	0.7778 (8)	0.0360 (4)	0.0328 (18)
C2	0.4039 (5)	0.8134 (10)	0.0565 (4)	0.0369 (19)
H2	0.424975	0.869023	0.102633	0.044*
C3	0.4564 (5)	0.7701 (10)	0.0117 (5)	0.043 (2)
H3	0.511854	0.797298	0.027182	0.052*
C4	0.4263 (5)	0.6851 (10)	−0.0572 (4)	0.041 (2)
C5	0.3421 (5)	0.6441 (10)	−0.0770 (4)	0.041 (2)
H5	0.320654	0.584154	−0.121905	0.049*
C6	0.2918 (5)	0.6909 (10)	−0.0316 (4)	0.0368 (19)
H6	0.236312	0.663756	−0.046372	0.044*
C7	0.5570 (6)	0.6793 (14)	−0.0882 (7)	0.075 (3)
H7A	0.563794	0.799177	−0.083723	0.112*
H7B	0.581299	0.638488	−0.128077	0.112*
H7C	0.583353	0.627100	−0.040354	0.112*
C8	0.2633 (5)	0.8351 (10)	0.0836 (5)	0.043 (2)
H8A	0.284919	0.937115	0.110847	0.052*
H8B	0.210510	0.862030	0.049830	0.052*
C9	0.1778 (5)	0.7024 (9)	0.6772 (4)	0.0312 (17)
C10	0.2372 (5)	0.7994 (10)	0.7252 (5)	0.043 (2)
H10	0.223555	0.867941	0.762396	0.052*
C11	0.3170 (5)	0.7928 (10)	0.7170 (5)	0.045 (2)
H11	0.357070	0.857191	0.749481	0.054*
C12	0.3383 (5)	0.6958 (10)	0.6635 (5)	0.0368 (19)
C13	0.2779 (5)	0.6029 (10)	0.6151 (4)	0.0390 (19)
H13	0.291633	0.537914	0.576832	0.047*
C14	0.1987 (5)	0.6038 (9)	0.6218 (4)	0.0351 (18)
H14	0.159200	0.538303	0.589320	0.042*
C15	0.0719 (6)	0.7992 (14)	0.7341 (6)	0.070 (3)
H15A	0.101521	0.771306	0.785338	0.105*
H15B	0.014064	0.784414	0.729689	0.105*
H15C	0.082611	0.914238	0.723309	0.105*
C16	0.4257 (5)	0.6896 (13)	0.6554 (7)	0.066 (3)
H16A	0.462467	0.706797	0.705434	0.079*
H16B	0.436524	0.578452	0.637616	0.079*
Br1	0.54615 (6)	0.74974 (14)	0.45961 (6)	0.0640 (3)
Br2	0.39836 (6)	0.99964 (10)	0.27210 (5)	0.0474 (3)
Br3	0.37040 (5)	0.48202 (10)	0.28754 (5)	0.0444 (3)
Br4	0.29050 (5)	0.81457 (11)	0.44107 (5)	0.0475 (3)
Cd1	0.40127 (4)	0.75364 (7)	0.36670 (3)	0.0405 (2)
N1	0.2515 (5)	0.7073 (8)	0.1396 (4)	0.0504 (19)
H1A	0.223587	0.620510	0.114873	0.076*
H1B	0.223546	0.752231	0.171145	0.076*
H1C	0.300243	0.672039	0.166698	0.076*
N2	0.4437 (5)	0.8145 (12)	0.6025 (5)	0.075 (3)
H2A	0.397883	0.839279	0.567472	0.112*
H2B	0.480916	0.773609	0.579280	0.112*
H2C	0.463229	0.907295	0.628329	0.112*
O1	0.4710 (4)	0.6390 (8)	−0.1067 (3)	0.0615 (18)
O2	0.0975 (3)	0.6926 (7)	0.6813 (3)	0.0493 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (4)	0.023 (4)	0.040 (4)	0.003 (3)	0.009 (4)	0.001 (3)
C2	0.038 (5)	0.041 (4)	0.031 (4)	−0.004 (4)	0.006 (4)	−0.001 (4)
C3	0.037 (5)	0.045 (5)	0.045 (5)	−0.007 (4)	0.002 (4)	0.003 (4)
C4	0.051 (5)	0.035 (4)	0.037 (5)	0.008 (4)	0.012 (4)	0.009 (4)
C5	0.050 (5)	0.037 (5)	0.033 (4)	0.002 (4)	0.004 (4)	−0.003 (4)
C6	0.032 (4)	0.035 (4)	0.040 (5)	−0.004 (3)	0.003 (4)	−0.001 (4)
C7	0.053 (7)	0.086 (8)	0.099 (9)	0.002 (6)	0.046 (6)	0.003 (7)
C8	0.053 (5)	0.039 (5)	0.042 (5)	0.008 (4)	0.019 (4)	0.000 (4)
C9	0.034 (4)	0.028 (4)	0.032 (4)	0.000 (3)	0.009 (3)	0.006 (3)
C10	0.054 (6)	0.037 (5)	0.039 (5)	−0.001 (4)	0.012 (4)	−0.008 (4)
C11	0.037 (5)	0.039 (5)	0.051 (5)	−0.008 (4)	−0.002 (4)	−0.005 (4)
C12	0.033 (4)	0.032 (4)	0.047 (5)	0.000 (3)	0.012 (4)	0.007 (4)
C13	0.046 (5)	0.037 (5)	0.040 (5)	0.000 (4)	0.022 (4)	−0.001 (4)
C14	0.034 (4)	0.038 (5)	0.036 (4)	−0.008 (3)	0.011 (4)	0.000 (4)
C15	0.060 (7)	0.081 (8)	0.087 (8)	−0.012 (6)	0.051 (6)	−0.017 (6)
C16	0.039 (6)	0.054 (6)	0.110 (9)	0.001 (4)	0.030 (6)	0.003 (6)
Br1	0.0371 (5)	0.0957 (8)	0.0570 (6)	0.0043 (5)	0.0072 (4)	−0.0010 (5)
Br2	0.0576 (5)	0.0397 (5)	0.0452 (5)	−0.0055 (4)	0.0127 (4)	0.0002 (4)
Br3	0.0452 (5)	0.0311 (4)	0.0594 (6)	−0.0011 (4)	0.0175 (4)	−0.0045 (4)
Br4	0.0446 (5)	0.0487 (5)	0.0548 (5)	0.0017 (4)	0.0229 (4)	−0.0016 (4)
Cd1	0.0388 (4)	0.0391 (4)	0.0457 (4)	−0.0014 (3)	0.0145 (3)	−0.0048 (3)
N1	0.063 (5)	0.043 (4)	0.052 (4)	0.006 (4)	0.027 (4)	0.003 (3)
N2	0.050 (5)	0.119 (7)	0.059 (5)	−0.036 (5)	0.022 (4)	−0.021 (5)
O1	0.061 (4)	0.081 (5)	0.050 (4)	0.011 (4)	0.028 (3)	−0.006 (3)
O2	0.038 (3)	0.049 (3)	0.065 (4)	−0.007 (3)	0.022 (3)	−0.011 (3)

Geometric parameters (Å, º) top

C1—C6	1.379 (11)	C11—C12	1.344 (12)
C1—C2	1.380 (10)	C11—H11	0.9300
C1—C8	1.503 (11)	C12—C13	1.380 (10)
C2—C3	1.369 (12)	C12—C16	1.507 (12)
C2—H2	0.9300	C13—C14	1.360 (10)
C3—C4	1.392 (11)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C4—O1	1.342 (10)	C15—O2	1.412 (11)
C4—C5	1.409 (11)	C15—H15A	0.9600
C5—C6	1.356 (11)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C6—H6	0.9300	C16—N2	1.452 (13)
C7—O1	1.435 (11)	C16—H16A	0.9700
C7—H7A	0.9600	C16—H16B	0.9700
C7—H7B	0.9600	Br1—Cd1	2.5968 (11)
C7—H7C	0.9600	Br2—Cd1	2.5798 (10)
C8—N1	1.474 (10)	Br3—Cd1	2.5659 (10)
C8—H8A	0.9700	Br4—Cd1	2.5761 (11)
C8—H8B	0.9700	N1—H1A	0.8900
C9—O2	1.367 (9)	N1—H1B	0.8900
C9—C14	1.374 (10)	N1—H1C	0.8900
C9—C10	1.385 (11)	N2—H2A	0.8900
C10—C11	1.380 (12)	N2—H2B	0.8900
C10—H10	0.9300	N2—H2C	0.8900

C6—C1—C2	117.4 (7)	C11—C12—C16	121.2 (8)
C6—C1—C8	120.7 (7)	C13—C12—C16	120.4 (8)
C2—C1—C8	121.9 (7)	C14—C13—C12	121.7 (8)
C3—C2—C1	122.7 (7)	C14—C13—H13	119.1
C3—C2—H2	118.7	C12—C13—H13	119.1
C1—C2—H2	118.7	C13—C14—C9	119.3 (7)
C2—C3—C4	119.6 (8)	C13—C14—H14	120.3
C2—C3—H3	120.2	C9—C14—H14	120.3
C4—C3—H3	120.2	O2—C15—H15A	109.5
O1—C4—C3	125.3 (8)	O2—C15—H15B	109.5
O1—C4—C5	117.0 (7)	H15A—C15—H15B	109.5
C3—C4—C5	117.8 (8)	O2—C15—H15C	109.5
C6—C5—C4	120.8 (7)	H15A—C15—H15C	109.5
C6—C5—H5	119.6	H15B—C15—H15C	109.5
C4—C5—H5	119.6	N2—C16—C12	113.5 (8)
C5—C6—C1	121.7 (7)	N2—C16—H16A	108.9
C5—C6—H6	119.1	C12—C16—H16A	108.9
C1—C6—H6	119.1	N2—C16—H16B	108.9
O1—C7—H7A	109.5	C12—C16—H16B	108.9
O1—C7—H7B	109.5	H16A—C16—H16B	107.7
H7A—C7—H7B	109.5	Br3—Cd1—Br4	111.65 (4)
O1—C7—H7C	109.5	Br3—Cd1—Br2	107.64 (4)
H7A—C7—H7C	109.5	Br4—Cd1—Br2	107.16 (4)
H7B—C7—H7C	109.5	Br3—Cd1—Br1	112.30 (4)
N1—C8—C1	112.8 (6)	Br4—Cd1—Br1	110.42 (4)
N1—C8—H8A	109.0	Br2—Cd1—Br1	107.41 (4)
C1—C8—H8A	109.0	C8—N1—H1A	109.5
N1—C8—H8B	109.0	C8—N1—H1B	109.5
C1—C8—H8B	109.0	H1A—N1—H1B	109.5
H8A—C8—H8B	107.8	C8—N1—H1C	109.5
O2—C9—C14	115.5 (7)	H1A—N1—H1C	109.5
O2—C9—C10	124.7 (7)	H1B—N1—H1C	109.5
C14—C9—C10	119.8 (7)	C16—N2—H2A	109.5
C11—C10—C9	118.9 (8)	C16—N2—H2B	109.5
C11—C10—H10	120.5	H2A—N2—H2B	109.5
C9—C10—H10	120.5	C16—N2—H2C	109.5
C12—C11—C10	121.8 (7)	H2A—N2—H2C	109.5
C12—C11—H11	119.1	H2B—N2—H2C	109.5
C10—C11—H11	119.1	C4—O1—C7	118.3 (7)
C11—C12—C13	118.4 (7)	C9—O2—C15	117.5 (6)

C6—C1—C2—C3	1.8 (11)	C9—C10—C11—C12	0.5 (13)
C8—C1—C2—C3	−176.3 (7)	C10—C11—C12—C13	0.9 (12)
C1—C2—C3—C4	−0.7 (12)	C10—C11—C12—C16	−179.9 (8)
C2—C3—C4—O1	178.6 (7)	C11—C12—C13—C14	−1.9 (12)
C2—C3—C4—C5	−1.3 (11)	C16—C12—C13—C14	178.9 (8)
O1—C4—C5—C6	−177.8 (7)	C12—C13—C14—C9	1.4 (12)
C3—C4—C5—C6	2.1 (12)	O2—C9—C14—C13	−178.5 (7)
C4—C5—C6—C1	−1.0 (12)	C10—C9—C14—C13	0.1 (11)
C2—C1—C6—C5	−1.0 (11)	C11—C12—C16—N2	−90.0 (11)
C8—C1—C6—C5	177.2 (7)	C13—C12—C16—N2	89.2 (10)
C6—C1—C8—N1	88.6 (9)	C3—C4—O1—C7	0.0 (13)
C2—C1—C8—N1	−93.3 (9)	C5—C4—O1—C7	179.9 (8)
O2—C9—C10—C11	177.4 (7)	C14—C9—O2—C15	−176.3 (8)
C14—C9—C10—C11	−1.0 (12)	C10—C9—O2—C15	5.3 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Br2	0.97	3.10	3.822 (8)	133
C8—H8B···Br1ⁱ	0.97	2.98	3.846 (9)	150
N1—H1A···Br4ⁱⁱ	0.89	2.62	3.439 (7)	154
N1—H1B···Br3ⁱⁱⁱ	0.89	2.63	3.450 (7)	154
N1—H1C···Br3	0.89	2.67	3.418 (7)	142
N2—H2A···Br4	0.89	2.54	3.380 (8)	157
N2—H2B···Br1	0.89	2.64	3.446 (8)	152
N2—H2C···Br1^iv	0.89	3.13	3.651 (10)	119
N2—H2C···Br2^iv	0.89	2.67	3.377 (7)	137
C10—H10···Cg2^v	0.93	2.88	3.682 (9)	145
C14—H14···Cg1ⁱⁱ	0.93	2.82	3.621 (8)	146

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x+1/2, y−1/2, −z+1/2; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x+1, −y+2, −z+1; (v) −x+1/2, y+1/2, −z+3/2.

Acknowledgements

The authors are thankful to the School of Pure and Applied Physics - MG University, Kottayam, Kerala 686 560, India, for the single-crystal XRD data.

Funding information

Funding for this research was provided by: Council of Scientific and Industrial Research (CSIR), New Delhi, India [grant No. 03(1301)13/EMR II to CR].

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