Synthesis, crystallographic analysis and Hirshfeld surface analysis of 4-bromo-2-{[2-(5-bromo-2-nitro­phen­yl)hydrazin-1-yl­idene]meth­yl}-5-fluoro­phenol

Yaman, M.; Aydemir, E.; Dege, N.; Agar, E.; Iskenderov, T.S.

doi:10.1107/S2056989018014627

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 11| November 2018| Pages 1628-1632

https://doi.org/10.1107/S2056989018014627

Open

access

Synthesis, crystallographic analysis and Hirshfeld surface analysis of 4-bromo-2-{[2-(5-bromo-2-nitrophenyl)hydrazin-1-ylidene]methyl}-5-fluorophenol

Mavise Yaman,^a Ercan Aydemir,^b,^c Necmi Dege,^a Erbil Agar ^b and Turganbay S. Iskenderov ^d ^*

^aOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, Turkey, ^bOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Chemistry, 55139, Samsun, Turkey, ^cMinistry of Forestry and Water Affairs , 11th Regional Directorate, 55030, Ilkadım-Samsun, Turkey, and ^dTaras Shevchenko National University of Kyiv, Department of Chemistry, 64, Vladimirska Str., Kiev 01601, Ukraine
^*Correspondence e-mail: tiskenderov@ukr.net

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 10 October 2018; accepted 16 October 2018; online 19 October 2018)

The title compound, C₁₃H₈Br₂FN₃O₃, is nearly planar with a dihedral angle of 10.6 (4)° between the two benzene rings. Intramolecular N—H⋯O and O—H⋯N hydrogen bonds occur. In the crystal, the molecules are linked by weak C—H⋯O and C—H⋯Br hydrogen bonds. The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis.

Keywords: crystal structure; Hirshfeld surface; Hydrazone; crystal structure; hydrogen bonding; 5-bromo-4-fluoro-2-hydroxybenzaldehyde.

CCDC reference: 1864935

1. Chemical context

Hydrazones, the most important derivatives of carboxaldehyde, are widely used both in organic synthesis and in industrial work because of their reaction abilities, such as ring closing, oxidation-reduction, replacement reactions and coupling (Öztürk et al., 2003 ). They are generally considered to be useful starting materials for the production of pharmaceuticals, pesticides, textile dyestuffs as well as compounds that serve as stabilizers and inhibitors in photography (Kaban & Ocal, 1993 ). In addition, they exhibit a wide range of applications in the fields of biology, optics, catalysis and analytical chemistry. Their broad spectrum of biological activities includes antimicrobial, antifungal, antiviral, antitumor, anti-HIV, anti-inflammatory, antineoplastic and analgesic activities (Sudheer et al., 2015 ; Soujanya & Rajitha, 2017 ). Hydrazone-based molecular switches, metalloassemblies and sensors have also been developed (Sudheer et al., 2015). Unlike oximes (Sliva et al., 1997 ; Penkova et al., 2010 ; Pavlishchuk et al., 2010 ), hydrazones are mostly obtained as a mixture of E and Z isomers and both isomers are generally weak acids (Mori et al., 2015 ). Tautomerism between the isomers might also occur in the case of the hydrazone and azo forms (Aydemir & Kaban, 2018 ). In this study, the structure of the newly synthesized compound has been evaluated by spectroscopic techniques. In view of this, in order to obtain information about the stereochemistry of the molecule and to confirm the assigned structure, X-ray analysis of the title compound was undertaken.

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The dihedral angle between the aromatic rings is 10.6 (4)°. The N1—N2 and N2–C8 bond lengths are 1.368 (7) and 1.374 (8) Å, respectively. The C13–N3 bond [1.451 (8) Å] in the nitro group is close to the standard value for this type of bond (Allen et al., 1987 ). Intramolecular N2—H2⋯O3 and O1—H1⋯N1 hydrogen-bonding interactions (Table 1) occur.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.91	2.631 (7)	146
N2—H2⋯O3	0.86	2.01	2.619 (7)	127
N2—H2⋯O3ⁱ	0.86	2.50	3.293 (7)	155
C4—H4⋯O1ⁱⁱ	0.93	2.60	3.494 (8)	162
C7—H7⋯O3ⁱ	0.93	2.66	3.461 (7)	145
C12—H12⋯Br1ⁱⁱⁱ	0.93	3.02	3.908 (7)	161
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
An ORTEP view of 4-bromo-2-{[2-(5-bromo-2-nitrophenyl)hydrazin-1-ylidene]methyl}-5-fluorophenol. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, the molecules are linked by weak C—H⋯O and C—H⋯Br hydrogen bonds (Table 1, Fig. 2).

Figure 2
The view of the crystal packing of the title compound.

4. Hirshfeld surface analysis

A Hirshfeld surface analysis was performed to quantify the nature of the intermolecular interactions. The Hirshfeld surfaces were generated using CrystalExplorer17.5 (Turner et al., 2017 ) using a standard (high) surface resolution. Fig. 3 shows the Hirshfeld surfaces mapped over d_norm in the range −0.2247 (red) to 1.3787 (blue) a.u. If the value of d_norm is negative, the intermolecular contacts are shorter than the van der Waals radius; these are shown as red regions. A positive value of d_norm, shown in blue, indicates that the intermolecular contacts are longer than the van der Waals radius (Şen et al., 2017 ). The red regions on the d_norm surface correspond to C—H⋯O hydrogen-bonding interactions, which comprise 20.2% of the total Hirshfeld surfaces.

Figure 3
Views of the Hirshfeld surface of the title compound mapped over d_norm.

The two-dimensional fingerprint (FP) plots are used to analyse significant differences between the intermolecular interaction patterns (Gumus et al., 2018 ; Kansız & Dege, 2018 ; Kansiz et al., 2018 ). Fig. 4 represents the FP plot for the sum of the contacts contributing to the Hirshfeld surface displayed in normal mode. In Fig. 5 distinct spikes indicate different interactions between two adjacent molecules in the crystal structure. The contribution from the Br⋯H/H⋯Br contacts make the largest (21.7%) to the Hirshfeld surface (Fig. 5b). The 20.2% contribution from the O—H⋯O hydrogen bond is seen as a pair of sharp spikes at d_e + d_i = 2.3 Å) in Fig. 5a. The distribution of positive and negative potential over the Hirshfeld surface is represented in Fig. 6 (positive electrostatic potential shown in blue region and negative electrostatic potential in red).

Figure 4
Fingerprint plot of the title compound showing all interactions.

Figure 5
Two-dimensional fingerprint plots with a d_norm view of the (a) O⋯H/H⋯O (20.2%), (b) Br⋯H/H⋯Br (21.7%), (c) F⋯H/H⋯F (7.4%), (d) C⋯H/H⋯C (9.7%), (e) N⋯H/H⋯N (3.3%) and (f) H⋯H (6.0%) contacts in the title compound.

Figure 6
A view of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential.

5. Database survey

There are no direct precedents for the structure of C₁₃H₈Br₂FN₃O₃ in the crystallographic literature (CSD, version 5.39, update of May 2018; Groom et al., 2016 ) but some similar structures including 2-nitrophenylhydrazine have been reported. All geometric parameters in the title compound agree well with those reported in the literature with the N1—N2 and N2—C8 bond distances being comparable to those in N-(4-chloro-2-nitrophenyl)-N′-methyl-N-(quinolin-4-ylmethylene)hydrazine [1.367 (2) and 1.386 (3) Å; Karadayı et al., 2005 ] and N-(4-bromo-2-nitrophenyl)-N-methyl-N′-(quinolin-4-ylmethylene)hydrazine [1.359 (3) and 1.393 (4) Å; Öztürk et al., 2003].

6. Synthesis and crystallization

5-Bromo-4-fluoro-2-hydroxybenzaldehyde (0.5 mmol) was dissolved in hot absolute ethanol (10 mL) and an equimolar amount of 5-bromo-2-nitrophenylhydrazine, dissolved in a minimum volume of absolute ethanol, was slowly added. The product appeared in the first minute. The reaction mixture was refluxed for an additional hour to complete the condensation and then allowed to cool in room temperature. The separated solid was then filtered and washed with ethanol and diethyl ether. The crude product was recrystallized from toluene as pink needle-shaped crystals, 96% yield, m.p. 569–570 K (dec.). The reaction scheme is shown in Fig. 7. UV (CHCl₃): λ_max 340, 430 nm; IR (KBr): υ 3610 (–OH), 3285 and 1155 (N—H), 3120–2985 (=C—H), 2915 (C—H), 1608 (C=N), 1558 (C=C), 1515 (N—N), 1475 and 1310 (N=O), 1195, 690 and 665 (C—X) cm⁻¹; MS (ESI⁺): 434.01 ([M + H]⁺, C₁₃H₈Br₂FN₃O₃; calculated 433.03).

Figure 7
The synthesis of the title compound.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound hydrogen atoms were positioned geometrically and refined using a riding model: C—H = 0.93–0.97 Å with U_iso(H) = 1.2U_eq(C)

Table 2
Experimental details

Crystal data
Chemical formula	C₁₃H₈Br₂FN₃O₃
M_r	433.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	16.1360 (14), 4.1745 (3), 21.468 (2)
β (°)	95.026 (7)
V (Å³)	1440.5 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	5.65
Crystal size (mm)	0.46 × 0.17 × 0.02

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.296, 0.883
No. of measured, independent and observed [I > 2σ(I)] reflections	9546, 2775, 1270
R_int	0.113
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.098, 0.84
No. of reflections	2775
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.28
Computer programs: X-AREA and X-RED (Stoe & Cie, 2002), SHELXT2014 (Sheldrick, 2015a ), SHELXL2017 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1864935

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018014627/xu5944sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018014627/xu5944Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018014627/xu5944Isup3.cml

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-Bromo-2-{[2-(5-bromo-2-nitrophenyl)hydrazin-1-ylidene]methyl}-5-fluorophenol top

Crystal data top

C₁₃H₈Br₂FN₃O₃	F(000) = 840
M_r = 433.04	D_x = 1.997 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 16.1360(14) Å	Cell parameters from 5914 reflections
b = 4.1745 (3) Å	θ = 1.5–29.7°
c = 21.468 (2) Å	µ = 5.65 mm⁻¹
β = 95.026 (7)°	T = 296 K
V = 1440.5 (2) Å³	Needle, pink
Z = 4	0.46 × 0.17 × 0.02 mm

Data collection top

Stoe IPDS 2 diffractometer	2775 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1270 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.113
rotation method scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −19→19
T_min = 0.296, T_max = 0.883	k = −4→5
9546 measured reflections	l = −26→26

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0267P)²] where P = (F_o² + 2F_c²)/3
S = 0.84	(Δ/σ)_max < 0.001
2775 reflections	Δρ_max = 0.42 e Å⁻³
200 parameters	Δρ_min = −0.28 e Å⁻³

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
Br2	0.19136 (4)	−0.4176 (2)	0.67484 (4)	0.0714 (3)
Br1	0.12607 (5)	1.1323 (3)	0.25304 (4)	0.0787 (3)
O3	0.5159 (3)	0.2810 (14)	0.5457 (2)	0.0689 (16)
F1	−0.0194 (2)	0.9500 (15)	0.3236 (2)	0.107 (2)
N1	0.2772 (3)	0.3510 (15)	0.4968 (3)	0.0503 (14)
N3	0.5145 (3)	0.0903 (18)	0.5895 (3)	0.0566 (15)
N2	0.3538 (3)	0.2591 (14)	0.5232 (3)	0.0564 (18)
H2	0.398154	0.325205	0.507843	0.068*
O2	0.5792 (3)	−0.0104 (14)	0.6187 (2)	0.0800 (19)
O1	0.1152 (3)	0.4263 (18)	0.4954 (3)	0.0892 (19)
H1	0.161084	0.357911	0.508414	0.134*
C8	0.3593 (4)	0.0605 (18)	0.5745 (3)	0.0470 (18)
C1	0.1976 (4)	0.8061 (17)	0.3618 (3)	0.0496 (19)
H1A	0.248599	0.848552	0.346371	0.060*
C13	0.4351 (4)	−0.0228 (17)	0.6077 (3)	0.050 (2)
C7	0.2755 (4)	0.5174 (18)	0.4473 (3)	0.050 (2)
H7	0.324917	0.564799	0.430059	0.060*
C11	0.3659 (4)	−0.3285 (19)	0.6826 (3)	0.062 (2)
H11	0.367763	−0.454009	0.718527	0.074*
C12	0.4369 (4)	−0.2110 (18)	0.6608 (3)	0.053 (2)
H12	0.487920	−0.259040	0.682367	0.064*
C6	0.1965 (4)	0.636 (2)	0.4169 (3)	0.0542 (19)
C9	0.2876 (4)	−0.0681 (18)	0.5974 (3)	0.0497 (18)
H9	0.236095	−0.024328	0.576206	0.060*
C10	0.2909 (4)	−0.2535 (18)	0.6492 (3)	0.055 (2)
C2	0.1272 (4)	0.913 (2)	0.3293 (3)	0.0569 (19)
C5	0.1212 (4)	0.584 (2)	0.4414 (3)	0.067 (2)
C4	0.0481 (4)	0.692 (2)	0.4105 (4)	0.078 (3)
H4	−0.002785	0.660131	0.426706	0.093*
C3	0.0533 (4)	0.849 (2)	0.3552 (3)	0.067 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.0566 (5)	0.0778 (7)	0.0821 (6)	−0.0020 (5)	0.0197 (4)	0.0045 (5)
Br1	0.0781 (6)	0.0915 (8)	0.0632 (5)	−0.0096 (5)	−0.0115 (4)	0.0140 (5)
O3	0.053 (3)	0.084 (5)	0.070 (3)	0.002 (3)	0.007 (3)	0.023 (3)
F1	0.052 (2)	0.167 (6)	0.098 (3)	0.020 (3)	−0.010 (2)	0.037 (3)
N1	0.043 (3)	0.054 (5)	0.053 (4)	0.006 (3)	−0.002 (3)	−0.005 (3)
N3	0.046 (3)	0.066 (5)	0.058 (4)	−0.002 (4)	0.002 (3)	−0.006 (4)
N2	0.040 (3)	0.070 (5)	0.060 (4)	0.003 (3)	0.008 (3)	0.006 (3)
O2	0.040 (3)	0.116 (6)	0.082 (4)	0.010 (3)	−0.006 (3)	0.016 (3)
O1	0.052 (3)	0.136 (6)	0.080 (4)	0.010 (4)	0.011 (3)	0.042 (4)
C8	0.043 (4)	0.056 (5)	0.043 (4)	0.003 (4)	0.005 (3)	−0.004 (4)
C1	0.042 (4)	0.049 (6)	0.058 (5)	−0.001 (3)	0.002 (3)	0.000 (4)
C13	0.040 (4)	0.053 (6)	0.060 (5)	−0.004 (3)	0.007 (3)	−0.006 (4)
C7	0.033 (4)	0.068 (7)	0.048 (4)	−0.004 (3)	0.005 (3)	0.000 (4)
C11	0.064 (5)	0.069 (7)	0.053 (4)	0.007 (4)	0.010 (4)	0.009 (4)
C12	0.043 (4)	0.061 (6)	0.054 (4)	0.009 (4)	−0.004 (3)	−0.003 (4)
C6	0.041 (4)	0.073 (6)	0.047 (4)	−0.002 (4)	0.001 (3)	0.001 (4)
C9	0.041 (4)	0.047 (5)	0.061 (4)	0.007 (4)	0.007 (3)	−0.011 (4)
C10	0.059 (4)	0.056 (6)	0.049 (4)	0.012 (4)	0.006 (4)	−0.001 (4)
C2	0.049 (4)	0.059 (5)	0.062 (4)	−0.003 (4)	0.003 (3)	−0.007 (4)
C5	0.041 (4)	0.097 (7)	0.064 (5)	0.003 (5)	0.010 (4)	0.018 (5)
C4	0.042 (4)	0.124 (9)	0.069 (5)	0.008 (5)	0.012 (4)	0.015 (5)
C3	0.041 (4)	0.093 (7)	0.062 (5)	0.009 (4)	−0.019 (4)	−0.002 (5)

Geometric parameters (Å, º) top

Br2—C10	1.872 (7)	C1—H1A	0.9300
Br1—C2	1.874 (7)	C13—C12	1.383 (9)
O3—N3	1.234 (7)	C7—C6	1.465 (9)
F1—C3	1.369 (7)	C7—H7	0.9300
N1—C7	1.268 (8)	C11—C12	1.366 (9)
N1—N2	1.368 (7)	C11—C10	1.388 (9)
N3—O2	1.243 (7)	C11—H11	0.9300
N3—C13	1.451 (8)	C12—H12	0.9300
N2—C8	1.374 (8)	C6—C5	1.383 (8)
N2—H2	0.8600	C9—C10	1.353 (10)
O1—C5	1.343 (8)	C9—H9	0.9300
O1—H1	0.8200	C2—C3	1.386 (9)
C8—C9	1.402 (8)	C5—C4	1.378 (10)
C8—C13	1.406 (9)	C4—C3	1.363 (10)
C1—C2	1.356 (9)	C4—H4	0.9300
C1—C6	1.381 (9)

C7—N1—N2	117.0 (5)	C11—C12—H12	119.0
O3—N3—O2	122.2 (6)	C13—C12—H12	119.0
O3—N3—C13	119.4 (6)	C1—C6—C5	119.0 (6)
O2—N3—C13	118.4 (6)	C1—C6—C7	118.6 (6)
N1—N2—C8	119.6 (5)	C5—C6—C7	122.4 (6)
N1—N2—H2	120.2	C10—C9—C8	122.3 (6)
C8—N2—H2	120.2	C10—C9—H9	118.9
C5—O1—H1	109.5	C8—C9—H9	118.9
N2—C8—C9	120.9 (6)	C9—C10—C11	121.6 (7)
N2—C8—C13	123.3 (6)	C9—C10—Br2	118.6 (5)
C9—C8—C13	115.8 (6)	C11—C10—Br2	119.8 (6)
C2—C1—C6	122.5 (6)	C1—C2—C3	116.2 (7)
C2—C1—H1A	118.8	C1—C2—Br1	123.6 (5)
C6—C1—H1A	118.8	C3—C2—Br1	120.1 (5)
C12—C13—C8	120.9 (6)	O1—C5—C4	116.9 (6)
C12—C13—N3	116.9 (6)	O1—C5—C6	122.5 (6)
C8—C13—N3	122.2 (6)	C4—C5—C6	120.5 (7)
N1—C7—C6	120.9 (6)	C3—C4—C5	117.5 (6)
N1—C7—H7	119.6	C3—C4—H4	121.2
C6—C7—H7	119.6	C5—C4—H4	121.2
C12—C11—C10	117.5 (7)	C4—C3—F1	117.7 (6)
C12—C11—H11	121.2	C4—C3—C2	124.2 (6)
C10—C11—H11	121.2	F1—C3—C2	118.1 (7)
C11—C12—C13	122.0 (6)

C7—N1—N2—C8	−175.6 (6)	C13—C8—C9—C10	1.7 (10)
N1—N2—C8—C9	4.6 (10)	C8—C9—C10—C11	−0.3 (12)
N1—N2—C8—C13	−174.2 (6)	C8—C9—C10—Br2	−179.0 (5)
N2—C8—C13—C12	176.8 (7)	C12—C11—C10—C9	−0.7 (11)
C9—C8—C13—C12	−2.1 (10)	C12—C11—C10—Br2	178.0 (5)
N2—C8—C13—N3	−1.4 (10)	C6—C1—C2—C3	1.4 (12)
C9—C8—C13—N3	179.7 (6)	C6—C1—C2—Br1	−177.9 (6)
O3—N3—C13—C12	−173.8 (7)	C1—C6—C5—O1	−178.7 (8)
O2—N3—C13—C12	6.4 (9)	C7—C6—C5—O1	1.5 (13)
O3—N3—C13—C8	4.4 (10)	C1—C6—C5—C4	1.6 (13)
O2—N3—C13—C8	−175.3 (7)	C7—C6—C5—C4	−178.3 (8)
N2—N1—C7—C6	−177.9 (6)	O1—C5—C4—C3	−179.2 (9)
C10—C11—C12—C13	0.3 (11)	C6—C5—C4—C3	0.6 (14)
C8—C13—C12—C11	1.2 (11)	C5—C4—C3—F1	178.3 (8)
N3—C13—C12—C11	179.5 (7)	C5—C4—C3—C2	−1.9 (14)
C2—C1—C6—C5	−2.6 (12)	C1—C2—C3—C4	1.0 (13)
C2—C1—C6—C7	177.3 (7)	Br1—C2—C3—C4	−179.8 (8)
N1—C7—C6—C1	−177.6 (7)	C1—C2—C3—F1	−179.3 (7)
N1—C7—C6—C5	2.3 (12)	Br1—C2—C3—F1	−0.1 (11)
N2—C8—C9—C10	−177.2 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.631 (7)	146
N2—H2···O3	0.86	2.01	2.619 (7)	127
N2—H2···O3ⁱ	0.86	2.50	3.293 (7)	155
C4—H4···O1ⁱⁱ	0.93	2.60	3.494 (8)	162
C7—H7···O3ⁱ	0.93	2.66	3.461 (7)	145
C12—H12···Br1ⁱⁱⁱ	0.93	3.02	3.908 (7)	161

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CSD CrossRef Web of Science Google Scholar
Aydemir, E. & Kaban, S. (2018). Asian J. Chem. 30, 1460–1464. CrossRef Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gumus, M. K., Kansiz, S., Dege, N. & Kalibabchuk, V. A. (2018). Acta Cryst. E74, 1211–1214. CrossRef IUCr Journals Google Scholar
Kaban, S. & Ocal, N. (1993). Pak. J. Sci. Ind. Res. 36, 357–359. Google Scholar
Kansız, S. & Dege, N. (2018). J. Mol. Struct. 1173, 42–51. Google Scholar
Kansiz, S., Macit, M., Dege, N. & Tsapyuk, G. G. (2018). Acta Cryst. E74, 1513–1516. CrossRef IUCr Journals Google Scholar
Karadayı, N., Aydemir, E., Kazak, C., Kirpi, E., Tuğcu, F. T., Gümü˛ş, M. K. & Kaban, Ş. (2005). Acta Cryst. E61, o2671–o2673. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mori, A., Suzuki, T. & Nakajima, K. (2015). Acta Cryst. E71, 142–145. CrossRef IUCr Journals Google Scholar
Öztürk, S., Akkurt, M., Aydemír, E. & Fun, H.-K. (2003). Acta Cryst. E59, o488–o489. CrossRef IUCr Journals Google Scholar
Pavlishchuk, A. V., Kolotilov, S. V., Zeller, M., Thompson, L. K., Fritsky, I. O., Addison, A. W. & Hunter, A. D. (2010). Eur. J. Inorg. Chem. pp. 4851–4858. Web of Science CSD CrossRef Google Scholar
Penkova, L., Demeshko, S., Pavlenko, V. A., Dechert, S., Meyer, F. & Fritsky, I. O. (2010). Inorg. Chim. Acta, 363, 3036–3040. Web of Science CSD CrossRef CAS Google Scholar
Şen, F., Kansiz, S. & Uçar, İ. (2017). Acta Cryst. C73, 517–524. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sliva, T. Yu., Duda, A. M., Głowiak, T., Fritsky, I. O., Amirkhanov, V. M., Mokhir, A. A. & Kozłowski, H. (1997). J. Chem. Soc. Dalton Trans. pp. 273–276. CSD CrossRef Web of Science Google Scholar
Soujanya, M. & Rajitha, G. (2017). Int. J. Pharm. Sci. Res. 8, 3786–3794. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Sudheer, R., Sithambaresan, M., Sajitha, N. R., Manoj, E. & Kurup, M. R. P. (2015). Acta Cryst. E71, 702–705. CrossRef IUCr Journals Google Scholar
Turner, M. J., MacKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17.5. University of Western Australia, Perth. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.