(1Z)-1-[(2E)-3-(4-Bromo­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-yl­idene]-2-(2,4-dinitro­phen­yl)hydrazine

Kant, R.; Gupta, V.K.; Kapoor, K.; Sapnakumari, M.; Sarojini, B.K.; Narayana, B.

doi:10.1107/S1600536812027328

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2193

https://doi.org/10.1107/S1600536812027328

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(1Z)-1-[(2E)-3-(4-Bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-ylidene]-2-(2,4-dinitrophenyl)hydrazine

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a M. Sapnakumari,^b B. K. Sarojini ^c and B. Narayana ^b

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P.A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 11 June 2012; accepted 16 June 2012; online 23 June 2012)

In the title molecule, C₂₁H₁₄BrFN₄O₄, the mean planes of the two nitro groups form dihedral angles of 3.1 (2) and 7.1 (5)° with the benzene ring to which they are attached. The dinitro-substituted ring forms dihedral angles of 8.6 (2) and 71.9 (2)° with the bromo- and fluoro-substituted benzene rings, respectively. The dihedral angle between the bromo- and fluoro-substituted benzene rings is 80.6 (2)°. There is an intramolecular N—H⋯O hydrogen bond. In the crystal, pairs of weak C—H⋯O hydrogen bonds form inversion dimers. In addition, π–π stacking interactions between the bromo- and dinitro-substituted rings [centroid–centroid separation = 3.768 (2) Å] are observed.

Related literature

For applications of hydrazone derivatives, see: Rollas et al. (2007 ); Singh et al. (1982 ). For the synthesis, see: Jasinski et al. (2010 ). For a related structure, see: Yin et al. (2009 ).

Experimental

Crystal data

C₂₁H₁₄BrFN₄O₄
M_r = 485.27
Monoclinic, P 2₁ /c
a = 15.0738 (12) Å
b = 10.6511 (5) Å
c = 14.3353 (8) Å
β = 116.010 (9)°
V = 2068.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.03 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.889, T_max = 1.000
15619 measured reflections
4058 independent reflections
2232 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.141
S = 1.01
4058 reflections
280 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯O1	0.86	1.95	2.584 (4)	130
C11—H11⋯O4ⁱ	0.93	2.45	3.316 (7)	154
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812027328/lh5491sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812027328/lh5491Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812027328/lh5491Isup3.cml

checkCIF report

Comment top

Hydrazone derivatives are important biologically active compounds which have received attention from the synthetic community (Rollas et al., 2007). Hydrazone derivatives are also used as analytical reagents (Singh et al., 1982). The crystal structure of 1-(but-2-enylidene)-2-(2-nitrophenyl)hydrazine has been reported (Yin et al., 2009). In order to prepare a pyrazoline derivative, (2E)-3-(4-bromophenyl) -1-(4-fluorophenyl)prop-2-en-1-one was reacted with 2,4-dinitrophenyl hydrazine as for the method of Jasinski et al. (2010). But, instead of a pyrazoline derivative a 2,4-dintrophenylhydrazone compound (I) was obtained and its crystal structure is reported herein.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those which are related in a reported structure (Yin et al., 2009). The two nitro groups form dihedral angles of 3.1 (2) and 7.1 (5)° with the C16-C21 ring. The dinitro substituted ring (C16-C21) forms dihedral angles of 8.6 (2)° and 71.9 (2) ° with bromo (C1-C6) and fluoro (C10-C15) substituted benzene rings, respectively. The dihedral angle between the bromo and fluoro substituted benzene rings is 80.6 (2)°. There is an intramolecular N—H···O hydrogen bond and in the crystal, pairs of weak C—H···O hydrogen bonds form inversion dimers (Table 1, Fig. 2). In addition, π–π stacking interactions between the bromophenyl ring and dinitro phenyl ring are observed [centroid separation = 3.768 (2) Å, interplanar spacing =3.410 Å, centroid shift = 1.60 Å, Symmetry = x, 1 + y, z].

Related literature top

For applications of hydrazone derivatives, see: Rollas et al. (2007); Singh et al. (1982). For the synthesis, see: Jasinski et al. (2010). For a related structure, see: Yin et al. (2009).

Experimental top

A mixture of (2E)-3-(4-bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (3.05 g, 0.01 mol) and 2,4-dinitrophenylhydrazine (1.98 g, 0.01 mol) in 50 ml of glacial acetic acid was refluxed for 6 hrs. The reaction mixture was cooled to produce red crystals (m.p. 414–416 K). X-ray quality crystals were obtained by slow evaporation of an acetic acid solution of (I) at room temperature.

Structure description top

For applications of hydrazone derivatives, see: Rollas et al. (2007); Singh et al. (1982). For the synthesis, see: Jasinski et al. (2010). For a related structure, see: Yin et al. (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with ellipsoids drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii. The dashed line indicates a hydrogen bond.
	Fig. 2. The packing arrangement of molecules viewed along the b axis. The broken lines show intermolecular C—H···O interactions.

(1Z)-1-[(2E)-3-(4-Bromophenyl)-1-(4-fluorophenyl)prop-2-en-1- ylidene]-2-(2,4-dinitrophenyl)hydrazine top

Crystal data top

C₂₁H₁₄BrFN₄O₄	F(000) = 976
M_r = 485.27	D_x = 1.558 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 416–414 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.0738 (12) Å	Cell parameters from 3762 reflections
b = 10.6511 (5) Å	θ = 3.6–29.0°
c = 14.3353 (8) Å	µ = 2.03 mm⁻¹
β = 116.010 (9)°	T = 293 K
V = 2068.5 (2) Å³	Plate, red
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4058 independent reflections
Radiation source: fine-focus sealed tube	2232 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.6°
ω scans	h = −18→18
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −13→13
T_min = 0.889, T_max = 1.000	l = −17→17
15619 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0533P)² + 0.8232P] where P = (F_o² + 2F_c²)/3
4058 reflections	(Δ/σ)_max = 0.001
280 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₁H₁₄BrFN₄O₄	V = 2068.5 (2) Å³
M_r = 485.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.0738 (12) Å	µ = 2.03 mm⁻¹
b = 10.6511 (5) Å	T = 293 K
c = 14.3353 (8) Å	0.3 × 0.2 × 0.1 mm
β = 116.010 (9)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4058 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2232 reflections with I > 2σ(I)
T_min = 0.889, T_max = 1.000	R_int = 0.045
15619 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	Δρ_max = 0.30 e Å⁻³
4058 reflections	Δρ_min = −0.40 e Å⁻³
280 parameters

Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Br1	0.10475 (5)	1.47051 (5)	0.45912 (4)	0.1080 (3)
F1	0.0359 (3)	0.6564 (3)	−0.06938 (19)	0.1523 (14)
N2	0.3279 (2)	0.5513 (3)	0.3799 (2)	0.0541 (7)
H21	0.3030	0.5395	0.3139	0.065*
O1	0.3072 (2)	0.3913 (3)	0.23628 (19)	0.0930 (10)
O2	0.3459 (3)	0.1980 (3)	0.2728 (2)	0.0946 (10)
O3	0.4846 (3)	0.0425 (4)	0.6152 (3)	0.1316 (16)
O4	0.5243 (3)	0.1687 (4)	0.7432 (3)	0.1200 (13)
N3	0.3419 (3)	0.3052 (4)	0.2993 (2)	0.0700 (9)
N1	0.3238 (2)	0.6688 (3)	0.4176 (2)	0.0581 (8)
N4	0.4898 (3)	0.1471 (5)	0.6501 (4)	0.0932 (12)
C1	0.1384 (3)	1.3158 (4)	0.4190 (3)	0.0624 (10)
C2	0.1915 (3)	1.2297 (4)	0.4951 (3)	0.0620 (10)
H2	0.2122	1.2492	0.5648	0.074*
C3	0.2135 (3)	1.1146 (4)	0.4666 (3)	0.0615 (10)
H3	0.2490	1.0559	0.5173	0.074*
C4	0.1829 (3)	1.0855 (3)	0.3623 (3)	0.0574 (9)
C5	0.1301 (3)	1.1750 (4)	0.2885 (3)	0.0655 (10)
H5	0.1090	1.1564	0.2186	0.079*
C6	0.1080 (3)	1.2911 (4)	0.3162 (3)	0.0692 (11)
H6	0.0732	1.3507	0.2660	0.083*
C7	0.2021 (3)	0.9630 (3)	0.3285 (3)	0.0621 (10)
H7	0.1672	0.9451	0.2581	0.074*
C8	0.2633 (3)	0.8747 (3)	0.3863 (3)	0.0613 (10)
H8	0.3046	0.8936	0.4553	0.074*
C9	0.2700 (3)	0.7506 (3)	0.3489 (3)	0.0560 (9)
C10	0.2108 (3)	0.7207 (3)	0.2368 (3)	0.0523 (9)
C11	0.2375 (4)	0.7628 (4)	0.1622 (3)	0.0780 (12)
H11	0.2958	0.8080	0.1816	0.094*
C12	0.1792 (5)	0.7388 (5)	0.0598 (4)	0.0965 (17)
H12	0.1981	0.7659	0.0095	0.116*
C13	0.0950 (5)	0.6765 (5)	0.0324 (3)	0.0895 (16)
C14	0.0659 (3)	0.6315 (5)	0.1030 (4)	0.0905 (14)
H14	0.0074	0.5864	0.0822	0.109*
C15	0.1253 (3)	0.6545 (4)	0.2068 (3)	0.0695 (11)
H15	0.1068	0.6246	0.2566	0.083*
C16	0.3702 (2)	0.4545 (3)	0.4448 (2)	0.0495 (8)
C17	0.4066 (3)	0.4703 (4)	0.5530 (2)	0.0565 (9)
H17	0.4031	0.5488	0.5797	0.068*
C18	0.4465 (3)	0.3722 (4)	0.6188 (3)	0.0643 (11)
H18	0.4705	0.3840	0.6900	0.077*
C19	0.4517 (3)	0.2545 (4)	0.5802 (3)	0.0614 (10)
C20	0.4187 (3)	0.2341 (4)	0.4765 (3)	0.0614 (10)
H20	0.4231	0.1549	0.4516	0.074*
C21	0.3786 (2)	0.3336 (4)	0.4092 (2)	0.0537 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1532 (6)	0.0716 (4)	0.1080 (4)	0.0292 (3)	0.0652 (4)	−0.0073 (3)
F1	0.197 (3)	0.147 (3)	0.0548 (16)	0.047 (3)	0.0025 (18)	−0.0091 (17)
N2	0.0666 (19)	0.0520 (18)	0.0393 (15)	0.0087 (15)	0.0193 (14)	0.0017 (14)
O1	0.145 (3)	0.077 (2)	0.0458 (15)	0.027 (2)	0.0320 (17)	0.0036 (16)
O2	0.142 (3)	0.073 (2)	0.079 (2)	0.022 (2)	0.0581 (19)	−0.0100 (16)
O3	0.181 (4)	0.087 (3)	0.122 (3)	0.061 (3)	0.062 (3)	0.047 (2)
O4	0.114 (3)	0.140 (3)	0.074 (2)	0.031 (2)	0.0118 (19)	0.046 (2)
N3	0.085 (2)	0.072 (2)	0.058 (2)	0.015 (2)	0.0360 (18)	−0.0049 (19)
N1	0.0656 (19)	0.0526 (18)	0.0520 (17)	0.0019 (16)	0.0219 (15)	−0.0028 (16)
N4	0.084 (3)	0.099 (3)	0.086 (3)	0.026 (3)	0.028 (2)	0.040 (3)
C1	0.072 (3)	0.051 (2)	0.068 (2)	0.001 (2)	0.034 (2)	−0.003 (2)
C2	0.073 (3)	0.060 (2)	0.050 (2)	−0.002 (2)	0.025 (2)	−0.0078 (19)
C3	0.070 (3)	0.054 (2)	0.054 (2)	0.002 (2)	0.0223 (19)	0.0022 (19)
C4	0.066 (2)	0.049 (2)	0.054 (2)	−0.0019 (19)	0.0235 (19)	−0.0034 (18)
C5	0.084 (3)	0.055 (2)	0.051 (2)	−0.001 (2)	0.024 (2)	−0.0016 (19)
C6	0.081 (3)	0.062 (3)	0.057 (2)	0.010 (2)	0.023 (2)	0.005 (2)
C7	0.079 (3)	0.051 (2)	0.055 (2)	−0.004 (2)	0.028 (2)	−0.0027 (19)
C8	0.072 (3)	0.050 (2)	0.056 (2)	−0.004 (2)	0.022 (2)	−0.0055 (19)
C9	0.062 (2)	0.051 (2)	0.057 (2)	−0.0016 (19)	0.0279 (19)	0.0011 (19)
C10	0.066 (2)	0.0431 (19)	0.050 (2)	0.0094 (18)	0.0277 (19)	0.0034 (16)
C11	0.102 (3)	0.075 (3)	0.069 (3)	−0.005 (3)	0.049 (3)	0.003 (2)
C12	0.165 (6)	0.078 (3)	0.064 (3)	0.017 (4)	0.066 (4)	0.011 (3)
C13	0.120 (4)	0.080 (3)	0.042 (3)	0.036 (3)	0.011 (3)	−0.003 (2)
C14	0.073 (3)	0.096 (4)	0.081 (3)	0.009 (3)	0.013 (3)	−0.014 (3)
C15	0.072 (3)	0.077 (3)	0.058 (2)	0.003 (2)	0.026 (2)	0.001 (2)
C16	0.045 (2)	0.057 (2)	0.0428 (19)	0.0024 (17)	0.0162 (16)	0.0023 (17)
C17	0.058 (2)	0.061 (2)	0.046 (2)	−0.0004 (19)	0.0180 (18)	−0.0017 (18)
C18	0.051 (2)	0.091 (3)	0.0410 (19)	−0.002 (2)	0.0110 (17)	0.006 (2)
C19	0.050 (2)	0.071 (3)	0.058 (2)	0.013 (2)	0.0180 (19)	0.019 (2)
C20	0.058 (2)	0.061 (2)	0.065 (2)	0.0100 (19)	0.0274 (19)	0.007 (2)
C21	0.054 (2)	0.062 (2)	0.047 (2)	0.0077 (19)	0.0236 (17)	0.0017 (18)

Geometric parameters (Å, º) top

Br1—C1	1.886 (4)	C7—H7	0.9300
F1—C13	1.352 (5)	C8—C9	1.447 (5)
N2—C16	1.347 (4)	C8—H8	0.9300
N2—N1	1.376 (4)	C9—C10	1.491 (5)
N2—H21	0.8600	C10—C15	1.363 (5)
O1—N3	1.231 (4)	C10—C11	1.372 (5)
O2—N3	1.213 (4)	C11—C12	1.365 (6)
O3—N4	1.209 (5)	C11—H11	0.9300
O4—N4	1.223 (5)	C12—C13	1.330 (7)
N3—C21	1.455 (4)	C12—H12	0.9300
N1—C9	1.298 (4)	C13—C14	1.356 (7)
N4—C19	1.463 (5)	C14—C15	1.381 (5)
C1—C6	1.363 (5)	C14—H14	0.9300
C1—C2	1.381 (5)	C15—H15	0.9300
C2—C3	1.378 (5)	C16—C21	1.411 (5)
C2—H2	0.9300	C16—C17	1.411 (4)
C3—C4	1.393 (5)	C17—C18	1.359 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.386 (5)	C18—C19	1.386 (5)
C4—C7	1.464 (5)	C18—H18	0.9300
C5—C6	1.384 (5)	C19—C20	1.361 (5)
C5—H5	0.9300	C20—C21	1.381 (5)
C6—H6	0.9300	C20—H20	0.9300
C7—C8	1.324 (5)

C16—N2—N1	120.9 (3)	C15—C10—C11	118.9 (4)
C16—N2—H21	119.5	C15—C10—C9	119.1 (3)
N1—N2—H21	119.5	C11—C10—C9	121.9 (4)
O2—N3—O1	122.3 (3)	C12—C11—C10	120.4 (5)
O2—N3—C21	119.1 (3)	C12—C11—H11	119.8
O1—N3—C21	118.6 (3)	C10—C11—H11	119.8
C9—N1—N2	115.6 (3)	C13—C12—C11	119.6 (4)
O3—N4—O4	123.0 (4)	C13—C12—H12	120.2
O3—N4—C19	120.1 (4)	C11—C12—H12	120.2
O4—N4—C19	116.9 (5)	C12—C13—F1	119.3 (6)
C6—C1—C2	122.0 (4)	C12—C13—C14	122.3 (4)
C6—C1—Br1	119.4 (3)	F1—C13—C14	118.3 (6)
C2—C1—Br1	118.6 (3)	C13—C14—C15	118.2 (5)
C3—C2—C1	119.2 (3)	C13—C14—H14	120.9
C3—C2—H2	120.4	C15—C14—H14	120.9
C1—C2—H2	120.4	C10—C15—C14	120.6 (4)
C2—C3—C4	120.5 (3)	C10—C15—H15	119.7
C2—C3—H3	119.8	C14—C15—H15	119.7
C4—C3—H3	119.8	N2—C16—C21	122.7 (3)
C5—C4—C3	118.4 (3)	N2—C16—C17	120.4 (3)
C5—C4—C7	119.4 (3)	C21—C16—C17	116.9 (3)
C3—C4—C7	122.2 (3)	C18—C17—C16	120.8 (4)
C6—C5—C4	121.7 (3)	C18—C17—H17	119.6
C6—C5—H5	119.2	C16—C17—H17	119.6
C4—C5—H5	119.2	C17—C18—C19	120.3 (3)
C1—C6—C5	118.3 (4)	C17—C18—H18	119.9
C1—C6—H6	120.9	C19—C18—H18	119.9
C5—C6—H6	120.9	C20—C19—C18	121.5 (3)
C8—C7—C4	127.6 (3)	C20—C19—N4	118.0 (4)
C8—C7—H7	116.2	C18—C19—N4	120.5 (4)
C4—C7—H7	116.2	C19—C20—C21	118.6 (4)
C7—C8—C9	124.0 (3)	C19—C20—H20	120.7
C7—C8—H8	118.0	C21—C20—H20	120.7
C9—C8—H8	118.0	C20—C21—C16	122.0 (3)
N1—C9—C8	116.9 (3)	C20—C21—N3	116.1 (3)
N1—C9—C10	123.7 (3)	C16—C21—N3	121.9 (3)
C8—C9—C10	119.3 (3)

C16—N2—N1—C9	−171.1 (3)	F1—C13—C14—C15	−178.6 (4)
C6—C1—C2—C3	−0.8 (6)	C11—C10—C15—C14	−0.8 (6)
Br1—C1—C2—C3	177.7 (3)	C9—C10—C15—C14	176.3 (4)
C1—C2—C3—C4	0.3 (6)	C13—C14—C15—C10	0.0 (6)
C2—C3—C4—C5	0.0 (6)	N1—N2—C16—C21	−178.0 (3)
C2—C3—C4—C7	−178.1 (4)	N1—N2—C16—C17	3.5 (5)
C3—C4—C5—C6	0.3 (6)	N2—C16—C17—C18	177.9 (3)
C7—C4—C5—C6	178.4 (4)	C21—C16—C17—C18	−0.7 (5)
C2—C1—C6—C5	1.1 (6)	C16—C17—C18—C19	−0.3 (5)
Br1—C1—C6—C5	−177.4 (3)	C17—C18—C19—C20	1.0 (6)
C4—C5—C6—C1	−0.9 (6)	C17—C18—C19—N4	−176.7 (3)
C5—C4—C7—C8	168.4 (4)	O3—N4—C19—C20	−5.6 (6)
C3—C4—C7—C8	−13.6 (6)	O4—N4—C19—C20	175.9 (4)
C4—C7—C8—C9	172.9 (4)	O3—N4—C19—C18	172.3 (5)
N2—N1—C9—C8	179.3 (3)	O4—N4—C19—C18	−6.3 (6)
N2—N1—C9—C10	3.5 (5)	C18—C19—C20—C21	−0.6 (6)
C7—C8—C9—N1	−171.1 (4)	N4—C19—C20—C21	177.2 (3)
C7—C8—C9—C10	4.9 (6)	C19—C20—C21—C16	−0.5 (5)
N1—C9—C10—C15	75.0 (5)	C19—C20—C21—N3	−178.2 (3)
C8—C9—C10—C15	−100.7 (4)	N2—C16—C21—C20	−177.4 (3)
N1—C9—C10—C11	−108.0 (4)	C17—C16—C21—C20	1.1 (5)
C8—C9—C10—C11	76.3 (5)	N2—C16—C21—N3	0.2 (5)
C15—C10—C11—C12	0.1 (6)	C17—C16—C21—N3	178.7 (3)
C9—C10—C11—C12	−176.9 (4)	O2—N3—C21—C20	1.9 (5)
C10—C11—C12—C13	1.4 (7)	O1—N3—C21—C20	−178.6 (3)
C11—C12—C13—F1	177.9 (4)	O2—N3—C21—C16	−175.8 (4)
C11—C12—C13—C14	−2.3 (8)	O1—N3—C21—C16	3.7 (5)
C12—C13—C14—C15	1.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O1	0.86	1.95	2.584 (4)	130
C11—H11···O4ⁱ	0.93	2.45	3.316 (7)	154

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₄BrFN₄O₄
M_r	485.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.0738 (12), 10.6511 (5), 14.3353 (8)
β (°)	116.010 (9)
V (Å³)	2068.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.03
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.889, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15619, 4058, 2232
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 1.01
No. of reflections	4058
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.40

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···O1	0.86	1.95	2.584 (4)	130
C11—H11···O4ⁱ	0.93	2.45	3.316 (7)	154

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

RK acknowledges the Department of Science & Technology for access to single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003. BN thanks the UGC, New Delhi, Government of India, for the purchase of chemicals through the SAP–DRS–Phase 1 programme. MS thanks the DST, New Delhi, for providing financial help for this research work through the INSPIRE Research Fellowship scheme.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jasinski, J. P., Guild, C. J., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2010). Acta Cryst. E66, o1948–o1949. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rollas, S. & Güniz Küçükgüzel, S. (2007). Molecules, 12, 1910–1939. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77–84. CrossRef PubMed CAS Web of Science Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yin, Z.-G., Qian, H.-Y., Zhu, X.-W. & Zhang, C.-X. (2009). Acta Cryst. E65, o2491. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

(1Z)-1-[(2E)-3-(4-Bromo­phen­yl)-1-(4-fluoro­phen­yl)prop-2-en-1-yl­­idene]-2-(2,4-di­nitro­phen­yl)hydrazine

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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organic compounds

(1Z)-1-[(2E)-3-(4-Bromophenyl)-1-(4-fluorophenyl)prop-2-en-1-ylidene]-2-(2,4-dinitrophenyl)hydrazine