Literature DB >> 22199971

(E)-1-[1-(2-Chloro-phen-yl)ethyl-idene]-2-(2,4-dinitro-phen-yl)hydrazine.

Suchada Chantrapromma, Boonlerd Nilwanna, Patcharaporn Jansrisewangwong, Thawanrat Kobkeatthawin, Hoong-Kun Fun.

Abstract

The title mol-ecule, C(14)H(11)ClN(4)O(4), is in an E configuration and is twisted with the dihedral angle between the two benzene rings being 38.48 (8)°. The ethyl-idenehydrazine plane makes dihedral angles of 6.03 (10) and 44.04 (11)°, respectively, with the dinitro- and chloro-substituted benzene rings. The two nitro groups are essentially coplanar with the bound benzene ring, making dihedral angles of 0.9 (2) and 1.65 (18)°. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by a weak C-H⋯O inter-action into a chain along the c axis. The chains are further stacked along the b axis by a π-π inter-action with a centroid-centroid distance of 3.6088 (10) Å.

Entities: Chemical Disease Species

Year: 2011 PMID： 22199971 PMCID： PMC3239123 DOI： 10.1107/S160053681105001X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶); Jansrisewangwong et al. (2010 ▶); Nilwanna et al. (2011 ▶). For background to and the biological activity of hydrozones, see: Angelusiu et al. (2010 ▶); Bendre et al. (1998 ▶); Gokce et al. (2009 ▶); Li et al. (2008 ▶); Loncle et al. (2004 ▶).

Experimental

Crystal data

C14H11ClN4O4 M = 334.72 Monoclinic, a = 32.660 (3) Å b = 7.1435 (7) Å c = 13.4798 (13) Å β = 112.215 (2)° V = 2911.5 (5) Å3 Z = 8 Mo Kα radiation μ = 0.29 mm−1 T = 297 K 0.36 × 0.26 × 0.15 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.904, T max = 0.957 16146 measured reflections 4458 independent reflections 3036 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.127 S = 1.04 4458 reflections 213 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.24 e Å−3 Δρmin = −0.27 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681105001X/is5008sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105001X/is5008Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681105001X/is5008Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₁ClN₄O₄	F(000) = 1376
M_r = 334.72	D_x = 1.527 Mg m⁻³
Monoclinic, C2/c	Melting point = 478–479 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 32.660 (3) Å	Cell parameters from 4458 reflections
b = 7.1435 (7) Å	θ = 1.4–30.6°
c = 13.4798 (13) Å	µ = 0.29 mm⁻¹
β = 112.215 (2)°	T = 297 K
V = 2911.5 (5) Å³	Block, yellow
Z = 8	0.36 × 0.26 × 0.15 mm

Bruker APEXII CCD area-detector diffractometer	4458 independent reflections
Radiation source: sealed tube	3036 reflections with I > 2σ(I)
graphite	R_int = 0.028
φ and ω scans	θ_max = 30.6°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −46→46
T_min = 0.904, T_max = 0.957	k = −10→10
16146 measured reflections	l = −19→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0537P)² + 1.2234P] where P = (F_o² + 2F_c²)/3
4458 reflections	(Δ/σ)_max = 0.001
213 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Cl1	0.015926 (14)	0.34149 (7)	0.42093 (4)	0.06172 (16)
O1	0.06808 (4)	0.2345 (2)	0.95156 (10)	0.0573 (3)
O2	0.09965 (5)	0.2876 (2)	1.12043 (10)	0.0700 (4)
O3	0.24764 (5)	0.5021 (3)	1.28114 (10)	0.0848 (5)
O4	0.28607 (4)	0.5486 (3)	1.18505 (11)	0.0805 (5)
N1	0.11688 (4)	0.28366 (18)	0.72895 (9)	0.0409 (3)
N2	0.10981 (4)	0.2894 (2)	0.82297 (10)	0.0419 (3)
H1N1	0.0863 (7)	0.249 (3)	0.8280 (15)	0.053 (5)*
N3	0.10020 (4)	0.2853 (2)	1.03026 (11)	0.0449 (3)
N4	0.25170 (5)	0.5037 (2)	1.19483 (11)	0.0556 (4)
C1	0.14355 (5)	0.3406 (2)	0.91423 (11)	0.0360 (3)
C2	0.14038 (4)	0.3427 (2)	1.01624 (11)	0.0367 (3)
C3	0.17560 (5)	0.3958 (2)	1.10769 (11)	0.0408 (3)
H3A	0.1729	0.3959	1.1739	0.049*
C4	0.21443 (5)	0.4482 (2)	1.09923 (11)	0.0421 (3)
C5	0.21904 (5)	0.4482 (2)	1.00072 (12)	0.0457 (4)
H5A	0.2457	0.4844	0.9964	0.055*
C6	0.18447 (5)	0.3951 (2)	0.91068 (11)	0.0433 (3)
H6A	0.1879	0.3947	0.8453	0.052*
C7	0.08535 (5)	0.2174 (2)	0.64630 (11)	0.0385 (3)
C8	0.09681 (5)	0.2063 (2)	0.54960 (11)	0.0388 (3)
C9	0.06866 (5)	0.2561 (2)	0.44575 (12)	0.0425 (3)
C10	0.08208 (6)	0.2441 (3)	0.35979 (13)	0.0516 (4)
H10A	0.0628	0.2781	0.2915	0.062*
C11	0.12381 (7)	0.1822 (3)	0.37579 (14)	0.0565 (4)
H11A	0.1329	0.1738	0.3183	0.068*
C12	0.15241 (6)	0.1321 (3)	0.47736 (15)	0.0539 (4)
H12A	0.1807	0.0900	0.4882	0.065*
C13	0.13910 (5)	0.1445 (2)	0.56248 (13)	0.0456 (3)
H13A	0.1588	0.1109	0.6304	0.055*
C14	0.04246 (5)	0.1437 (3)	0.64700 (14)	0.0546 (4)
H14A	0.0482	0.0642	0.7082	0.082*
H14B	0.0276	0.0732	0.5827	0.082*
H14C	0.0241	0.2465	0.6505	0.082*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0465 (2)	0.0735 (3)	0.0510 (2)	0.0134 (2)	0.00243 (17)	0.0014 (2)
O1	0.0378 (6)	0.0795 (9)	0.0541 (7)	−0.0125 (6)	0.0168 (5)	−0.0065 (6)
O2	0.0663 (8)	0.1052 (11)	0.0496 (7)	−0.0225 (8)	0.0345 (6)	−0.0097 (7)
O3	0.0585 (8)	0.1510 (16)	0.0417 (7)	−0.0191 (9)	0.0154 (6)	−0.0282 (8)
O4	0.0416 (7)	0.1350 (14)	0.0594 (8)	−0.0233 (8)	0.0127 (6)	−0.0197 (9)
N1	0.0388 (6)	0.0484 (7)	0.0323 (6)	−0.0033 (5)	0.0097 (5)	−0.0021 (5)
N2	0.0358 (6)	0.0539 (8)	0.0343 (6)	−0.0052 (6)	0.0114 (5)	−0.0027 (5)
N3	0.0421 (7)	0.0511 (8)	0.0458 (7)	−0.0034 (6)	0.0214 (6)	−0.0025 (6)
N4	0.0406 (7)	0.0801 (11)	0.0413 (7)	−0.0039 (7)	0.0099 (6)	−0.0137 (7)
C1	0.0336 (6)	0.0390 (7)	0.0335 (6)	0.0020 (5)	0.0106 (5)	0.0000 (5)
C2	0.0334 (6)	0.0403 (7)	0.0381 (7)	0.0004 (5)	0.0152 (5)	−0.0013 (5)
C3	0.0409 (7)	0.0491 (8)	0.0338 (6)	0.0015 (6)	0.0156 (6)	−0.0038 (6)
C4	0.0338 (7)	0.0522 (9)	0.0358 (7)	0.0005 (6)	0.0079 (5)	−0.0063 (6)
C5	0.0331 (7)	0.0616 (10)	0.0427 (8)	−0.0019 (7)	0.0147 (6)	−0.0037 (7)
C6	0.0367 (7)	0.0597 (10)	0.0345 (7)	−0.0025 (7)	0.0147 (6)	−0.0016 (6)
C7	0.0343 (7)	0.0400 (7)	0.0359 (7)	0.0005 (6)	0.0072 (5)	0.0002 (6)
C8	0.0371 (7)	0.0383 (7)	0.0345 (6)	−0.0045 (6)	0.0062 (5)	−0.0045 (5)
C9	0.0408 (7)	0.0411 (8)	0.0366 (7)	−0.0020 (6)	0.0046 (6)	−0.0049 (6)
C10	0.0599 (10)	0.0528 (10)	0.0349 (7)	−0.0056 (8)	0.0099 (7)	−0.0042 (6)
C11	0.0673 (11)	0.0608 (11)	0.0454 (9)	−0.0083 (9)	0.0257 (8)	−0.0083 (8)
C12	0.0476 (9)	0.0564 (10)	0.0600 (10)	−0.0022 (8)	0.0229 (8)	−0.0086 (8)
C13	0.0394 (7)	0.0494 (9)	0.0415 (7)	−0.0004 (6)	0.0080 (6)	−0.0041 (6)
C14	0.0411 (8)	0.0684 (12)	0.0477 (9)	−0.0113 (8)	0.0094 (7)	0.0021 (8)

Cl1—C9	1.7364 (16)	C5—H5A	0.9300
O1—N3	1.2314 (17)	C6—H6A	0.9300
O2—N3	1.2224 (17)	C7—C8	1.488 (2)
O3—N4	1.2198 (19)	C7—C14	1.500 (2)
O4—N4	1.2213 (19)	C8—C13	1.397 (2)
N1—C7	1.2877 (17)	C8—C9	1.399 (2)
N1—N2	1.3720 (17)	C9—C10	1.388 (2)
N2—C1	1.3551 (18)	C10—C11	1.370 (3)
N2—H1N1	0.85 (2)	C10—H10A	0.9300
N3—C2	1.4537 (19)	C11—C12	1.381 (3)
N4—C4	1.4537 (19)	C11—H11A	0.9300
C1—C6	1.410 (2)	C12—C13	1.375 (2)
C1—C2	1.4176 (19)	C12—H12A	0.9300
C2—C3	1.384 (2)	C13—H13A	0.9300
C3—C4	1.368 (2)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.392 (2)	C14—H14C	0.9600
C5—C6	1.362 (2)

C7—N1—N2	116.82 (13)	N1—C7—C8	113.18 (13)
C1—N2—N1	118.92 (13)	N1—C7—C14	124.54 (14)
C1—N2—H1N1	118.0 (13)	C8—C7—C14	122.11 (13)
N1—N2—H1N1	122.6 (13)	C13—C8—C9	116.70 (14)
O2—N3—O1	122.17 (13)	C13—C8—C7	118.19 (13)
O2—N3—C2	118.61 (13)	C9—C8—C7	125.09 (14)
O1—N3—C2	119.21 (12)	C10—C9—C8	121.61 (15)
O3—N4—O4	122.76 (14)	C10—C9—Cl1	117.66 (12)
O3—N4—C4	119.10 (14)	C8—C9—Cl1	120.71 (12)
O4—N4—C4	118.13 (14)	C11—C10—C9	119.86 (15)
N2—C1—C6	119.97 (13)	C11—C10—H10A	120.1
N2—C1—C2	123.43 (13)	C9—C10—H10A	120.1
C6—C1—C2	116.60 (12)	C10—C11—C12	119.94 (16)
C3—C2—C1	121.74 (13)	C10—C11—H11A	120.0
C3—C2—N3	116.67 (12)	C12—C11—H11A	120.0
C1—C2—N3	121.58 (12)	C13—C12—C11	120.12 (16)
C4—C3—C2	119.05 (13)	C13—C12—H12A	119.9
C4—C3—H3A	120.5	C11—C12—H12A	119.9
C2—C3—H3A	120.5	C12—C13—C8	121.76 (15)
C3—C4—C5	121.16 (13)	C12—C13—H13A	119.1
C3—C4—N4	119.52 (13)	C8—C13—H13A	119.1
C5—C4—N4	119.31 (14)	C7—C14—H14A	109.5
C6—C5—C4	119.88 (14)	C7—C14—H14B	109.5
C6—C5—H5A	120.1	H14A—C14—H14B	109.5
C4—C5—H5A	120.1	C7—C14—H14C	109.5
C5—C6—C1	121.56 (13)	H14A—C14—H14C	109.5
C5—C6—H6A	119.2	H14B—C14—H14C	109.5
C1—C6—H6A	119.2

C7—N1—N2—C1	173.61 (14)	C4—C5—C6—C1	0.4 (3)
N1—N2—C1—C6	2.9 (2)	N2—C1—C6—C5	179.70 (15)
N1—N2—C1—C2	−176.94 (14)	C2—C1—C6—C5	−0.5 (2)
N2—C1—C2—C3	179.97 (14)	N2—N1—C7—C8	−176.69 (13)
C6—C1—C2—C3	0.1 (2)	N2—N1—C7—C14	−1.3 (2)
N2—C1—C2—N3	1.3 (2)	N1—C7—C8—C13	41.4 (2)
C6—C1—C2—N3	−178.56 (14)	C14—C7—C8—C13	−134.06 (16)
O2—N3—C2—C3	0.2 (2)	N1—C7—C8—C9	−137.42 (16)
O1—N3—C2—C3	−179.10 (15)	C14—C7—C8—C9	47.1 (2)
O2—N3—C2—C1	179.01 (15)	C13—C8—C9—C10	0.2 (2)
O1—N3—C2—C1	−0.3 (2)	C7—C8—C9—C10	179.06 (15)
C1—C2—C3—C4	0.2 (2)	C13—C8—C9—Cl1	−178.03 (12)
N3—C2—C3—C4	178.97 (14)	C7—C8—C9—Cl1	0.8 (2)
C2—C3—C4—C5	−0.2 (3)	C8—C9—C10—C11	0.0 (3)
C2—C3—C4—N4	−179.79 (15)	Cl1—C9—C10—C11	178.32 (14)
O3—N4—C4—C3	0.1 (3)	C9—C10—C11—C12	−0.1 (3)
O4—N4—C4—C3	179.51 (17)	C10—C11—C12—C13	−0.1 (3)
O3—N4—C4—C5	−179.43 (18)	C11—C12—C13—C8	0.3 (3)
O4—N4—C4—C5	−0.1 (3)	C9—C8—C13—C12	−0.4 (2)
C3—C4—C5—C6	−0.1 (3)	C7—C8—C13—C12	−179.31 (15)
N4—C4—C5—C6	179.48 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N1···O1	0.85 (2)	1.97 (2)	2.6081 (19)	131.2 (17)
C6—H6A···O3ⁱ	0.93	2.52	3.251 (2)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N1⋯O1	0.85 (2)	1.97 (2)	2.6081 (19)	131.2 (17)
C6—H6A⋯O3ⁱ	0.93	2.52	3.251 (2)	135

Symmetry code: (i) .

11 in total

1. Synthesis, characterization, antioxidant activity and DNA-binding studies of two rare earth(III) complexes with naringenin-2-hydroxy benzoyl hydrazone ligand.

Authors: Tian-Rong Li; Zheng-Yin Yang; Bao-Dui Wang; Dong-Dong Qin
Journal: Eur J Med Chem Date: 2007-10-11 Impact factor: 6.514

2. New Cu(II), Co(II), Ni(II) complexes with aroyl-hydrazone based ligand. Synthesis, spectroscopic characterization and in vitro antibacterial evaluation.

Authors: Madalina Veronica Angelusiu; Stefania-Felicia Barbuceanu; Constantin Draghici; Gabriela Laura Almajan
Journal: Eur J Med Chem Date: 2010-01-25 Impact factor: 6.514

3. Synthesis and antifungal activity of cholesterol-hydrazone derivatives.

Authors: Céline Loncle; Jean Michel Brunel; Nicolas Vidal; Michel Dherbomez; Yves Letourneux
Journal: Eur J Med Chem Date: 2004-12 Impact factor: 6.514

4. Synthesis and analgesic and anti-inflammatory activities 6-substituted-3(2H)-pyridazinone-2-acetyl-2-(p-substituted/nonsubstituted benzal)hydrazone derivatives.

Authors: Mehtap Gökçe; Semra Utku; Esra Küpeli
Journal: Eur J Med Chem Date: 2009-05-09 Impact factor: 6.514

5. (E,E)-1,2-Bis(2,4,6-trimeth-oxy-benzyl-idene)hydrazine.

Authors: Hoong-Kun Fun; Patcharaporn Jansrisewangwong; Suchada Chantrapromma
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-08-25

6. (E,E)-1,2-Bis[1-(2-bromo-phen-yl)ethyl-idene]hydrazine.

Authors: Patcharaporn Jansrisewangwong; Suchada Chantrapromma; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-07-31

7. (E)-1-(2,4-Dinitro-phen-yl)-2-[1-(2-meth-oxy-phen-yl)ethyl-idene]hydrazine.

Authors: Hoong-Kun Fun; Boonlerd Nilwanna; Patcharaporn Jansrisewangwong; Thawanrat Kobkeatthawin; Suchada Chantrapromma
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-11-05

8. (E)-1-(2,4-Dinitro-phen-yl)-2-[1-(2-nitro-phen-yl)ethyl-idene]hydrazine.

Authors: Boonlerd Nilwanna; Suchada Chantrapromma; Patcharaporn Jansrisewangwong; Hoong-Kun Fun
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-10-29

9. Synthesis and Characterization of Coordinatively Unsaturated Copper (II) Complexes of 1,3-Bis(2'-Pyridyl)-1,2-Diaza-2-Butene and Their Antityrosinase Activity.

Authors: R Bendre; A Murugkar; S Padhye; P Kulkarni; M Karve
Journal: Met Based Drugs Date: 1998