Crystal structure of (E)-1-(2-nitro­benzyl­idene)-2,2-di­phenyl­hydrazine

Flores-Alamo, M.; Meléndrez-Luévano, R.; Ortiz Márquez, J.A.; Sansinenea Royano, E.; Cabrera-Vivas, B.M.

doi:10.1107/S1600536814016109

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o909-o910

doi:10.1107/S1600536814016109

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Crystal structure of (E)-1-(2-nitrobenzylidene)-2,2-diphenylhydrazine

Marcos Flores-Alamo,^a ^* Ruth Meléndrez-Luévano,^b José A. Ortiz Márquez,^b Estibaliz Sansinenea Royano ^b and Blanca M. Cabrera-Vivas ^b

^aFacultad de Química, Universidad Nacional Autónoma de México, 04510, México DF, Mexico, and ^bFacultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla 72570, Puebla, Pue., Mexico
^*Correspondence e-mail: mfa@unam.mx

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 July 2014; accepted 10 July 2014; online 1 August 2014)

The title compound, C₁₉H₁₅N₃O₂, shows an E conformation of the imine bond. The dihedral angle between the planes of the phenyl rings in the diphenylhydrazine groups is 88.52 (4)°. The 2-nitrobenzene ring shows a torsion angle of 10.17 (8)° with the C=N—N plane. A short intramolecular C—H⋯O contact occurs. In the crystal, only van der Waals contacts occur between the molecules.

Keywords: crystal structure; hydrazine; hydrogen bonding.

CCDC reference: 1013341

1. Related literature

For background to hydrazide–hydrazone derivatives and their various biological activities, see: Sztanke et al. (2007 ); Al-Macrosaur et al. (2007 ); Roma et al. (2000 ); Smalley et al. (2006 ). For a related structure, see: Mendoza et al. (2012 ).

2. Experimental

2.1. Crystal data

C₁₉H₁₅N₃O₂
M_r = 317.34
Monoclinic, P 2₁ /n
a = 11.8536 (5) Å
b = 12.4293 (3) Å
c = 11.9492 (5) Å
β = 118.584 (5)°
V = 1545.92 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 140 K
0.59 × 0.49 × 0.27 mm

2.2. Data collection

Agilent Xcalibur Atlas Gemini diffractometer
Absorption correction: analytical (CrysAlis RED; Agilent, 2012 ) T_min = 0.961, T_max = 0.977
12199 measured reflections
3757 independent reflections
3057 reflections with I > 2σ(I)
R_int = 0.023

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.113
S = 1.03
3757 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O1	0.95	2.27	2.7822 (15)	113

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis RED (Agilent, 2012); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 1013341

Crystal structure: contains datablocks I, New_Global. DOI: 10.1107/S1600536814016109/hb7250sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016109/hb7250Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814016109/hb7250Isup3.cml

checkCIF report

Comment top

Hydrazides and hydrazones are present in many of the bioactive heterocyclic compounds that are of great interest because of their diverse biological and clinical applications, creating interest in researchers who have synthesized a variety of hydrazide-hydrazones derivatives and screened them for their various biological activities viz anticancer (Sztanke et al. 2007), anti-HIV (Al-Macrosaur et al. 2007), antimycobacterial, anti-inflammatory (Roma et al. 2000), antidiabetic, antimicrobial, as well antimalarial activities (Smalley et al. 2006). In the title compound C₁₉H₁₅N₃O₂, the discrete unit consist of one molecule showing an E configuration with respect to C=N for diphenylhydrazine group opposite to o-nitrophenyl ring (Fig. 1). The dihedral angle for the phenyl rings C1—C6 and C7—C12 is 88.52 (4)° very close to orthogonal form and this value is slightly higher than reported for positional isomer (E)-1-(4-nitrobenzylidene)-2,2-diphenylhydrazine (Mendoza et al. 2012). The dihedral angle for ortho-nitrophenyl ring and C=N—N plane is 10.17 (8) °, which evidences the coplanarity between these groups. The imine N2—C13, 1.2871 (15) Å bond distance is typical C=N bond. In the crystal array one intramolecular interaction C13—H13···O1 (2.27 Å) of type hydrogen bond is observed, and in the crystal packing intermolecular contacts of type van der Waals are observed growing along the a, b and c axes, resulting in a complex supramolecular array (Fig. 2).

Related literature top

For background to hydrazide–hydrazone derivatives and their various biological activities, see: Sztanke et al. (2007); Al-Macrosaur et al. (2007); Roma et al. (2000); Smalley et al. (2006). For a related structure, see: Mendoza et al. (2012).

Experimental top

228 mg (1.24 mmol) diphenylhydrazine were dissolved in ethanol and acetic acid (0.5 ml) was slowly added to this solution while stirring, 300 mg (1.24 mmol) of 2-nitrobenzaldehyde was added drop by drop into the above solution strongly stirring and the resulting mixture was kept at room temperature until it became orange transparent solution. After one and a half hours an orange solution precipitated. The reaction was monitored by TLC, aluminium Alugram Sil G/UV254. The mixture was separated with filtration in vacuo system and the precipitate was washed three times with cold methanol. Recrystallization was performed three times with ethanol, to obtain orange blocks (yield 91%, mp. 133–135°C). FT·IR (film): (cm^-1):3026 ν(C—H), 1577 ν(C=N), 1334,ν (NO2). ¹H NMR (400 MHz, (CD₃)₂CO: (d/ p.p.m., J/Hz):8.28 (dd,1H,C3), 7.91 (dd,1H,C5), 7.72 (m,1H,C4), 7.60 (s,1H,C=N),7.52(d, J = 1.44, 1H, C6),7.48 (m, 4H,C2') 7.25 (m,6H,C4', C2'). ¹³C NMR (400 MHz, (CD₃)₂CO): (d/ p.p.m.):143.16 (C2), 132.99 (C1'), 132.97 (C4), 130.41 (C=N), 130.13 (C6), 129.99 (C3'), 128.40 (C1), 127.72 (C3), 125.26 (C4'), 124.49 (C5), 122.41 (C2'). MS—EI: m/z 317.12.C₁₉H₁₅N₃O₂.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis RED (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as circles of arbitrary size.
	Fig. 2. The crystal packing in the title compound.

(E)-2-(2-Nitrobenzylidene)-2,2-diphenylhydrazine top

Crystal data top

C₁₉H₁₅N₃O₂	F(000) = 664
M_r = 317.34	D_x = 1.363 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6418 reflections
a = 11.8536 (5) Å	θ = 3.7–29.6°
b = 12.4293 (3) Å	µ = 0.09 mm⁻¹
c = 11.9492 (5) Å	T = 140 K
β = 118.584 (5)°	Block, yellow
V = 1545.92 (12) Å³	0.59 × 0.49 × 0.27 mm
Z = 4

Data collection top

Agilent Xcalibur Atlas Gemini diffractometer	3757 independent reflections
Graphite monochromator	3057 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.023
ω scans	θ_max = 29.6°, θ_min = 3.7°
Absorption correction: analytical (CrysAlis RED; Agilent, 2012)	h = −15→15
T_min = 0.961, T_max = 0.977	k = −17→13
12199 measured reflections	l = −12→16

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0546P)² + 0.3936P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.19 e Å⁻³
3757 reflections	Δρ_min = −0.29 e Å⁻³
217 parameters

Crystal data top

C₁₉H₁₅N₃O₂	V = 1545.92 (12) Å³
M_r = 317.34	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8536 (5) Å	µ = 0.09 mm⁻¹
b = 12.4293 (3) Å	T = 140 K
c = 11.9492 (5) Å	0.59 × 0.49 × 0.27 mm
β = 118.584 (5)°

Data collection top

Agilent Xcalibur Atlas Gemini diffractometer	3757 independent reflections
Absorption correction: analytical (CrysAlis RED; Agilent, 2012)	3057 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.977	R_int = 0.023
12199 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
3757 reflections	Δρ_min = −0.29 e Å⁻³
217 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.

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

	x	y	z	U_iso*/U_eq
N2	0.11331 (9)	0.25147 (8)	0.92802 (9)	0.0231 (2)
N1	0.22974 (9)	0.29935 (8)	0.97008 (10)	0.0258 (2)
C1	0.23071 (11)	0.41296 (9)	0.97290 (10)	0.0222 (2)
C6	0.11903 (11)	0.47065 (9)	0.94355 (11)	0.0241 (2)
H6	0.042	0.4335	0.9251	0.029*
C13	0.10253 (11)	0.14893 (9)	0.91111 (11)	0.0228 (2)
H13	0.1743	0.1053	0.9263	0.027*
C5	0.12018 (12)	0.58203 (10)	0.94130 (11)	0.0269 (3)
H5	0.0434	0.6206	0.9203	0.032*
C18	−0.18121 (12)	−0.04581 (10)	0.79564 (12)	0.0306 (3)
H18	−0.1998	−0.1194	0.7728	0.037*
C14	−0.02595 (11)	0.10233 (9)	0.86714 (10)	0.0212 (2)
C4	0.23172 (12)	0.63796 (10)	0.96930 (12)	0.0286 (3)
H4	0.2315	0.7143	0.9655	0.034*
C9	0.53623 (12)	0.14688 (10)	1.11874 (12)	0.0304 (3)
H9	0.5981	0.1224	1.2007	0.037*
C15	−0.12374 (11)	0.16652 (10)	0.86682 (11)	0.0256 (3)
H15	−0.1055	0.2396	0.8923	0.031*
C12	0.35602 (11)	0.21828 (10)	0.87944 (11)	0.0267 (3)
H12	0.2942	0.2428	0.7974	0.032*
C7	0.34034 (10)	0.23976 (9)	0.98487 (11)	0.0222 (2)
C2	0.34400 (12)	0.46897 (10)	1.00538 (13)	0.0319 (3)
H2	0.4216	0.4308	1.0292	0.038*
C8	0.42978 (11)	0.20381 (10)	1.10458 (11)	0.0275 (3)
H8	0.4182	0.2181	1.1765	0.033*
O2	0.00953 (12)	−0.17689 (8)	0.82260 (11)	0.0517 (3)
N3	0.02964 (11)	−0.08055 (9)	0.81874 (10)	0.0347 (3)
C19	−0.06012 (11)	−0.00479 (9)	0.82864 (11)	0.0243 (2)
C16	−0.24502 (12)	0.12733 (11)	0.83091 (12)	0.0307 (3)
H16	−0.3091	0.1738	0.8299	0.037*
C10	0.55296 (12)	0.12539 (10)	1.01392 (13)	0.0289 (3)
H10	0.6262	0.0865	1.0239	0.035*
C11	0.46250 (12)	0.16084 (10)	0.89447 (12)	0.0302 (3)
H11	0.4735	0.1457	0.8224	0.036*
C17	−0.27406 (12)	0.02027 (11)	0.79614 (12)	0.0327 (3)
H17	−0.3572	−0.0071	0.7729	0.039*
O1	0.11844 (10)	−0.04545 (9)	0.80403 (12)	0.0537 (3)
C3	0.34333 (13)	0.58067 (11)	1.00287 (14)	0.0341 (3)
H3	0.4208	0.6183	1.0246	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0200 (5)	0.0234 (5)	0.0265 (5)	−0.0030 (4)	0.0115 (4)	−0.0025 (4)
N1	0.0186 (5)	0.0219 (5)	0.0368 (6)	−0.0018 (4)	0.0132 (4)	−0.0053 (4)
C1	0.0231 (6)	0.0214 (6)	0.0236 (6)	−0.0019 (4)	0.0125 (4)	−0.0041 (4)
C6	0.0207 (5)	0.0248 (6)	0.0261 (6)	−0.0023 (4)	0.0107 (4)	−0.0017 (4)
C13	0.0219 (6)	0.0217 (6)	0.0240 (6)	0.0016 (4)	0.0102 (4)	−0.0004 (4)
C5	0.0259 (6)	0.0259 (6)	0.0285 (6)	0.0030 (5)	0.0128 (5)	−0.0004 (5)
C18	0.0324 (7)	0.0234 (6)	0.0277 (6)	−0.0069 (5)	0.0077 (5)	−0.0010 (5)
C14	0.0228 (5)	0.0211 (5)	0.0190 (5)	−0.0007 (4)	0.0093 (4)	0.0006 (4)
C4	0.0352 (7)	0.0209 (6)	0.0340 (7)	−0.0026 (5)	0.0200 (6)	−0.0040 (5)
C9	0.0222 (6)	0.0298 (7)	0.0296 (7)	−0.0013 (5)	0.0047 (5)	0.0030 (5)
C15	0.0250 (6)	0.0237 (6)	0.0300 (6)	−0.0029 (5)	0.0147 (5)	−0.0039 (4)
C12	0.0238 (6)	0.0301 (6)	0.0245 (6)	0.0031 (5)	0.0102 (5)	0.0033 (5)
C7	0.0183 (5)	0.0192 (5)	0.0294 (6)	−0.0025 (4)	0.0117 (4)	−0.0035 (4)
C2	0.0250 (6)	0.0274 (6)	0.0483 (8)	−0.0028 (5)	0.0216 (6)	−0.0088 (5)
C8	0.0260 (6)	0.0303 (6)	0.0248 (6)	−0.0040 (5)	0.0110 (5)	−0.0045 (5)
O2	0.0655 (8)	0.0209 (5)	0.0550 (7)	0.0089 (5)	0.0178 (6)	−0.0016 (4)
N3	0.0321 (6)	0.0263 (6)	0.0322 (6)	0.0054 (5)	0.0045 (4)	−0.0066 (4)
C19	0.0259 (6)	0.0213 (5)	0.0210 (5)	0.0012 (5)	0.0074 (4)	0.0007 (4)
C16	0.0251 (6)	0.0342 (7)	0.0353 (7)	−0.0010 (5)	0.0165 (5)	−0.0025 (5)
C10	0.0208 (6)	0.0234 (6)	0.0418 (7)	0.0023 (5)	0.0145 (5)	0.0001 (5)
C11	0.0299 (6)	0.0326 (7)	0.0335 (7)	0.0012 (5)	0.0195 (5)	−0.0016 (5)
C17	0.0251 (6)	0.0369 (7)	0.0330 (7)	−0.0095 (5)	0.0113 (5)	−0.0003 (5)
O1	0.0338 (6)	0.0464 (6)	0.0806 (8)	−0.0013 (5)	0.0271 (6)	−0.0269 (6)
C3	0.0310 (7)	0.0294 (7)	0.0502 (8)	−0.0093 (5)	0.0261 (6)	−0.0103 (6)

Geometric parameters (Å, º) top

N2—C13	1.2871 (15)	C9—H9	0.95
N2—N1	1.3593 (13)	C15—C16	1.3776 (17)
N1—C1	1.4125 (15)	C15—H15	0.95
N1—C7	1.4412 (14)	C12—C7	1.3845 (16)
C1—C2	1.3928 (16)	C12—C11	1.3849 (17)
C1—C6	1.3948 (16)	C12—H12	0.95
C6—C5	1.3849 (17)	C7—C8	1.3851 (16)
C6—H6	0.95	C2—C3	1.3887 (18)
C13—C14	1.4714 (15)	C2—H2	0.95
C13—H13	0.95	C8—H8	0.95
C5—C4	1.3856 (17)	O2—N3	1.2261 (15)
C5—H5	0.95	N3—O1	1.2274 (16)
C18—C17	1.3757 (19)	N3—C19	1.4674 (16)
C18—C19	1.3907 (17)	C16—C17	1.3874 (19)
C18—H18	0.95	C16—H16	0.95
C14—C19	1.4036 (16)	C10—C11	1.3844 (18)
C14—C15	1.4057 (16)	C10—H10	0.95
C4—C3	1.3821 (18)	C11—H11	0.95
C4—H4	0.95	C17—H17	0.95
C9—C10	1.3845 (18)	C3—H3	0.95
C9—C8	1.3846 (17)

C13—N2—N1	119.91 (10)	C7—C12—H12	120.3
N2—N1—C1	116.22 (9)	C11—C12—H12	120.3
N2—N1—C7	121.56 (9)	C12—C7—C8	120.52 (11)
C1—N1—C7	120.95 (9)	C12—C7—N1	119.85 (10)
C2—C1—C6	119.06 (11)	C8—C7—N1	119.63 (10)
C2—C1—N1	120.14 (10)	C3—C2—C1	119.92 (12)
C6—C1—N1	120.80 (10)	C3—C2—H2	120
C5—C6—C1	120.12 (11)	C1—C2—H2	120
C5—C6—H6	119.9	C9—C8—C7	119.57 (11)
C1—C6—H6	119.9	C9—C8—H8	120.2
N2—C13—C14	116.99 (10)	C7—C8—H8	120.2
N2—C13—H13	121.5	O2—N3—O1	123.23 (12)
C14—C13—H13	121.5	O2—N3—C19	117.53 (12)
C6—C5—C4	120.92 (11)	O1—N3—C19	119.22 (11)
C6—C5—H5	119.5	C18—C19—C14	122.52 (11)
C4—C5—H5	119.5	C18—C19—N3	115.57 (11)
C17—C18—C19	119.94 (11)	C14—C19—N3	121.90 (11)
C17—C18—H18	120	C15—C16—C17	120.31 (12)
C19—C18—H18	120	C15—C16—H16	119.8
C19—C14—C15	115.42 (10)	C17—C16—H16	119.8
C19—C14—C13	125.28 (10)	C11—C10—C9	119.72 (11)
C15—C14—C13	119.26 (10)	C11—C10—H10	120.1
C3—C4—C5	118.81 (11)	C9—C10—H10	120.1
C3—C4—H4	120.6	C10—C11—C12	120.40 (11)
C5—C4—H4	120.6	C10—C11—H11	119.8
C10—C9—C8	120.30 (11)	C12—C11—H11	119.8
C10—C9—H9	119.8	C18—C17—C16	119.32 (12)
C8—C9—H9	119.8	C18—C17—H17	120.3
C16—C15—C14	122.45 (11)	C16—C17—H17	120.3
C16—C15—H15	118.8	C4—C3—C2	121.07 (12)
C14—C15—H15	118.8	C4—C3—H3	119.5
C7—C12—C11	119.48 (11)	C2—C3—H3	119.5

C13—N2—N1—C1	173.38 (10)	N1—C1—C2—C3	177.32 (11)
C13—N2—N1—C7	6.11 (16)	C10—C9—C8—C7	−0.38 (18)
N2—N1—C1—C2	−175.12 (10)	C12—C7—C8—C9	0.64 (18)
C7—N1—C1—C2	−7.77 (16)	N1—C7—C8—C9	−179.78 (11)
N2—N1—C1—C6	4.95 (15)	C17—C18—C19—C14	2.08 (18)
C7—N1—C1—C6	172.30 (10)	C17—C18—C19—N3	−177.01 (11)
C2—C1—C6—C5	2.89 (17)	C15—C14—C19—C18	−1.66 (16)
N1—C1—C6—C5	−177.17 (11)	C13—C14—C19—C18	175.84 (11)
N1—N2—C13—C14	179.18 (9)	C15—C14—C19—N3	177.37 (10)
C1—C6—C5—C4	−0.71 (17)	C13—C14—C19—N3	−5.13 (17)
N2—C13—C14—C19	171.78 (11)	O2—N3—C19—C18	−22.36 (16)
N2—C13—C14—C15	−10.81 (16)	O1—N3—C19—C18	155.89 (12)
C6—C5—C4—C3	−1.63 (18)	O2—N3—C19—C14	158.54 (11)
C19—C14—C15—C16	−0.18 (17)	O1—N3—C19—C14	−23.21 (17)
C13—C14—C15—C16	−177.84 (11)	C14—C15—C16—C17	1.60 (19)
C11—C12—C7—C8	−0.34 (18)	C8—C9—C10—C11	−0.18 (19)
C11—C12—C7—N1	−179.92 (11)	C9—C10—C11—C12	0.48 (19)
N2—N1—C7—C12	80.11 (14)	C7—C12—C11—C10	−0.23 (19)
C1—N1—C7—C12	−86.56 (14)	C19—C18—C17—C16	−0.59 (19)
N2—N1—C7—C8	−99.47 (13)	C15—C16—C17—C18	−1.19 (19)
C1—N1—C7—C8	93.86 (13)	C5—C4—C3—C2	1.77 (19)
C6—C1—C2—C3	−2.75 (18)	C1—C2—C3—C4	0.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.95	2.27	2.7822 (15)	113

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.95	2.27	2.7822 (15)	113

Acknowledgements

We are grateful for financial support from projects CAVB-NAT-14 G, VIEP, BUAP and MELR-NAT-14 G. MFA thanks Dr A. L. Maldonado-Hermenegildo for useful comments.

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