Literature DB >> 22065394

(E)-1-(4-Chloro-benzyl-idene)-2-phenyl-hydrazine.

M Nawaz Tahir, Muhammad Ilyas Tariq, Riaz H Tariq, Muhammad Sarfraz.   

Abstract

The asymmetric unit of the title compound, C(13)H(11)ClN(2), contains two geometrically distinct mol-ecules; one mol-ecule is close to planar [dihedral angle between the aromatic rings = 2.44 (18)°] and the other is twisted about the linking hydrazide group [dihedral angle = 14.08 (19)°]. In the crystal, the N-H groups do not form hydrogen bonds and the mol-ecules are linked by weak C-H⋯π inter-actions.

Entities:  

Year:  2011        PMID： 22065394      PMCID： PMC3200606          DOI： 10.1107/S1600536811032958

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


Related literature

For related structures, see: Mufakkar et al. (2010 ▶); Shad et al. (2010 ▶); Yin et al. (2007 ▶).

Experimental

Crystal data

C13H11ClN2 M = 230.69 Orthorhombic, a = 18.6896 (9) Å b = 15.0250 (7) Å c = 8.4679 (4) Å V = 2377.9 (2) Å3 Z = 8 Mo Kα radiation μ = 0.29 mm−1 T = 296 K 0.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.983 10661 measured reflections 4631 independent reflections 2234 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.107 S = 0.96 4631 reflections 295 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.15 e Å−3 Δρmin = −0.12 e Å−3 Absolute structure: Flack (1983 ▶), 2120 Friedel pairs Flack parameter: 0.08 (8) Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032958/hb6364sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032958/hb6364Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811032958/hb6364Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H11ClN2F(000) = 960
Mr = 230.69Dx = 1.289 Mg m−3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 2234 reflections
a = 18.6896 (9) Åθ = 2.6–26.0°
b = 15.0250 (7) ŵ = 0.29 mm−1
c = 8.4679 (4) ÅT = 296 K
V = 2377.9 (2) Å3Prism, yellow
Z = 80.30 × 0.22 × 0.18 mm
Bruker Kappa APEXII CCD diffractometer4631 independent reflections
Radiation source: fine-focus sealed tube2234 reflections with I > 2σ(I)
graphiteRint = 0.047
Detector resolution: 7.80 pixels mm-1θmax = 26.0°, θmin = 2.6°
ω scansh = −23→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −18→8
Tmin = 0.972, Tmax = 0.983l = −10→10
10661 measured reflections
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107w = 1/[σ2(Fo2) + (0.034P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max < 0.001
4631 reflectionsΔρmax = 0.15 e Å−3
295 parametersΔρmin = −0.12 e Å−3
1 restraintAbsolute structure: Flack (1983), 2120 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.08 (8)
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.
xyzUiso*/Ueq
Cl10.65074 (8)−0.28852 (7)0.04443 (17)0.1121 (6)
N10.7409 (2)0.2275 (3)0.1957 (4)0.0747 (16)
N20.71259 (15)0.1473 (2)0.1565 (3)0.0620 (12)
C10.7116 (2)0.3043 (3)0.1339 (4)0.0570 (17)
C20.6470 (2)0.3045 (2)0.0531 (5)0.0600 (16)
C30.6199 (2)0.3839 (3)−0.0015 (4)0.0680 (16)
C40.6544 (2)0.4633 (3)0.0205 (5)0.0700 (17)
C50.7189 (2)0.4618 (3)0.0988 (4)0.0733 (17)
C60.7466 (2)0.3843 (3)0.1566 (5)0.0667 (16)
C70.7460 (2)0.0782 (3)0.2017 (4)0.0660 (17)
C80.7209 (2)−0.0111 (3)0.1679 (5)0.0610 (16)
C90.6539 (2)−0.0276 (3)0.1025 (4)0.0690 (17)
C100.6317 (2)−0.1110 (3)0.0677 (4)0.0733 (17)
C110.6769 (3)−0.1823 (3)0.0953 (5)0.0763 (19)
C120.7428 (3)−0.1686 (3)0.1634 (6)0.0880 (19)
C130.7642 (2)−0.0834 (3)0.1987 (5)0.0830 (17)
Cl20.05113 (6)0.19759 (6)0.67491 (15)0.0891 (5)
N30.09142 (18)0.7174 (2)0.4688 (4)0.0713 (14)
N40.07889 (14)0.6368 (2)0.5353 (3)0.0569 (11)
C140.07671 (18)0.7951 (2)0.5497 (4)0.0550 (14)
C150.0503 (2)0.7956 (3)0.7018 (4)0.0627 (17)
C160.0368 (2)0.8752 (3)0.7763 (5)0.0723 (17)
C170.0484 (2)0.9564 (3)0.7053 (5)0.0727 (17)
C180.0740 (2)0.9553 (3)0.5522 (5)0.0740 (19)
C190.0884 (2)0.8767 (3)0.4756 (5)0.0670 (17)
C200.09573 (19)0.5686 (3)0.4543 (4)0.0613 (16)
C210.08497 (18)0.4782 (2)0.5112 (4)0.0527 (14)
C220.1035 (2)0.4073 (3)0.4174 (4)0.0730 (16)
C230.0947 (2)0.3208 (3)0.4663 (5)0.0763 (17)
C240.0658 (2)0.3056 (3)0.6128 (4)0.0580 (16)
C250.0479 (2)0.3741 (3)0.7092 (4)0.0617 (16)
C260.05611 (19)0.4603 (2)0.6581 (5)0.0590 (14)
H10.782 (2)0.228 (2)0.231 (5)0.0899*
H20.622340.251540.036150.0718*
H30.576490.38355−0.055300.0817*
H40.634930.51639−0.016170.0842*
H50.744140.514570.112550.0878*
H60.789570.385380.211950.0798*
H70.788200.085120.258630.0790*
H90.623580.020120.082040.0825*
H100.58637−0.120360.025470.0879*
H120.77257−0.216560.185310.1056*
H130.80890−0.074350.244340.0998*
H3A0.113 (2)0.720 (2)0.369 (4)0.0858*
H150.041560.742180.753900.0750*
H160.019070.874110.878930.0867*
H170.039371.009530.757940.0874*
H180.081671.008940.499980.0888*
H190.106070.877910.372940.0803*
H200.115700.576920.354740.0736*
H220.122600.418160.317810.0874*
H230.108060.273640.401530.0915*
H250.030180.362720.809790.0739*
H260.042060.507050.722970.0710*
U11U22U33U12U13U23
Cl10.1692 (12)0.0627 (8)0.1044 (9)−0.0202 (8)−0.0151 (10)0.0053 (7)
N10.067 (3)0.063 (2)0.094 (3)−0.002 (2)−0.019 (2)−0.004 (2)
N20.063 (2)0.056 (2)0.067 (2)0.0003 (18)−0.0010 (19)−0.003 (2)
C10.055 (3)0.060 (3)0.056 (3)−0.003 (2)0.006 (2)−0.013 (2)
C20.062 (3)0.056 (3)0.062 (2)−0.009 (2)−0.005 (2)−0.010 (2)
C30.070 (3)0.072 (3)0.062 (2)0.004 (2)−0.012 (2)−0.003 (2)
C40.087 (3)0.056 (3)0.067 (3)−0.001 (2)0.002 (2)−0.010 (2)
C50.079 (3)0.064 (3)0.077 (3)−0.017 (2)0.011 (2)−0.016 (2)
C60.057 (2)0.064 (3)0.079 (3)−0.005 (2)−0.001 (2)−0.012 (3)
C70.060 (3)0.068 (3)0.070 (3)0.004 (3)−0.008 (2)−0.004 (2)
C80.056 (3)0.065 (3)0.062 (2)0.004 (2)−0.006 (2)−0.002 (2)
C90.069 (3)0.061 (3)0.077 (3)0.007 (2)−0.006 (2)0.000 (2)
C100.077 (3)0.074 (3)0.069 (3)−0.001 (3)−0.007 (2)0.002 (3)
C110.101 (4)0.062 (3)0.066 (3)−0.015 (3)0.000 (3)0.009 (2)
C120.100 (4)0.058 (3)0.106 (3)0.011 (3)−0.009 (3)0.011 (3)
C130.070 (3)0.072 (3)0.107 (3)0.008 (3)−0.023 (3)0.013 (3)
Cl20.1246 (9)0.0516 (7)0.0911 (8)−0.0030 (6)−0.0040 (8)0.0068 (7)
N30.104 (3)0.049 (2)0.061 (2)0.0020 (19)0.0193 (19)0.0028 (18)
N40.068 (2)0.044 (2)0.0586 (19)0.0062 (16)−0.0039 (17)0.0035 (17)
C140.060 (2)0.049 (3)0.056 (2)0.0028 (19)0.001 (2)0.000 (2)
C150.077 (3)0.051 (3)0.060 (3)0.007 (2)0.004 (2)0.013 (2)
C160.084 (3)0.063 (3)0.070 (3)0.009 (2)0.012 (2)−0.003 (2)
C170.088 (3)0.060 (3)0.070 (3)−0.004 (2)−0.001 (2)0.007 (2)
C180.088 (3)0.041 (3)0.093 (4)−0.004 (2)−0.003 (3)0.014 (2)
C190.076 (3)0.057 (3)0.068 (3)−0.002 (2)0.011 (2)0.014 (2)
C200.074 (3)0.057 (3)0.053 (2)0.004 (2)0.004 (2)0.000 (2)
C210.062 (3)0.043 (2)0.053 (2)0.0034 (18)0.0001 (19)−0.0053 (19)
C220.099 (3)0.060 (3)0.060 (2)0.006 (2)0.018 (2)−0.001 (2)
C230.102 (3)0.059 (3)0.068 (3)0.014 (2)0.010 (2)−0.012 (2)
C240.069 (3)0.042 (2)0.063 (3)−0.002 (2)−0.010 (2)0.0058 (19)
C250.081 (3)0.053 (3)0.051 (2)0.001 (2)0.003 (2)0.003 (2)
C260.069 (2)0.056 (3)0.052 (2)0.012 (2)0.003 (2)−0.011 (2)
Cl1—C111.724 (5)C7—H70.9300
Cl2—C241.728 (4)C9—H90.9300
N1—N21.357 (5)C10—H100.9300
N1—C11.380 (6)C12—H120.9300
N2—C71.271 (5)C13—H130.9300
N1—H10.82 (4)C14—C191.395 (5)
N3—C141.381 (4)C14—C151.379 (5)
N3—N41.356 (4)C15—C161.376 (6)
N4—C201.273 (5)C16—C171.377 (6)
N3—H3A0.94 (3)C17—C181.382 (6)
C1—C61.382 (6)C18—C191.374 (6)
C1—C21.388 (5)C20—C211.455 (5)
C2—C31.376 (5)C21—C261.382 (5)
C3—C41.369 (6)C21—C221.373 (5)
C4—C51.376 (5)C22—C231.374 (6)
C5—C61.365 (6)C23—C241.372 (5)
C7—C81.450 (6)C24—C251.356 (6)
C8—C131.380 (6)C25—C261.374 (5)
C8—C91.392 (5)C15—H150.9300
C9—C101.353 (6)C16—H160.9300
C10—C111.384 (6)C17—H170.9300
C11—C121.376 (8)C18—H180.9300
C12—C131.374 (6)C19—H190.9300
C2—H20.9300C20—H200.9300
C3—H30.9300C22—H220.9300
C4—H40.9300C23—H230.9300
C5—H50.9300C25—H250.9300
C6—H60.9300C26—H260.9300
N2—N1—C1119.7 (3)C11—C12—H12120.00
N1—N2—C7117.4 (3)C13—C12—H12120.00
N2—N1—H1117 (2)C12—C13—H13119.00
C1—N1—H1120 (2)C8—C13—H13119.00
N4—N3—C14121.0 (3)N3—C14—C15122.6 (3)
N3—N4—C20116.9 (3)N3—C14—C19119.3 (3)
C14—N3—H3A119.8 (19)C15—C14—C19118.1 (3)
N4—N3—H3A119.1 (19)C14—C15—C16119.9 (4)
N1—C1—C6119.1 (4)C15—C16—C17122.8 (4)
N1—C1—C2122.3 (4)C16—C17—C18117.0 (4)
C2—C1—C6118.6 (4)C17—C18—C19121.4 (4)
C1—C2—C3119.2 (3)C14—C19—C18120.8 (4)
C2—C3—C4122.4 (4)N4—C20—C21122.6 (3)
C3—C4—C5117.7 (4)C22—C21—C26117.9 (3)
C4—C5—C6121.3 (4)C20—C21—C22119.9 (3)
C1—C6—C5120.8 (4)C20—C21—C26122.2 (3)
N2—C7—C8122.5 (3)C21—C22—C23122.0 (3)
C7—C8—C9122.3 (4)C22—C23—C24118.5 (4)
C7—C8—C13120.1 (4)Cl2—C24—C25119.4 (3)
C9—C8—C13117.6 (4)Cl2—C24—C23119.6 (3)
C8—C9—C10121.9 (4)C23—C24—C25121.0 (4)
C9—C10—C11119.5 (4)C24—C25—C26119.9 (3)
Cl1—C11—C12119.8 (4)C21—C26—C25120.7 (3)
C10—C11—C12120.1 (4)C14—C15—H15120.00
Cl1—C11—C10120.1 (4)C16—C15—H15120.00
C11—C12—C13119.4 (4)C15—C16—H16119.00
C8—C13—C12121.5 (4)C17—C16—H16119.00
C3—C2—H2120.00C16—C17—H17122.00
C1—C2—H2120.00C18—C17—H17122.00
C2—C3—H3119.00C17—C18—H18119.00
C4—C3—H3119.00C19—C18—H18119.00
C3—C4—H4121.00C14—C19—H19120.00
C5—C4—H4121.00C18—C19—H19120.00
C4—C5—H5119.00N4—C20—H20119.00
C6—C5—H5119.00C21—C20—H20119.00
C5—C6—H6120.00C21—C22—H22119.00
C1—C6—H6120.00C23—C22—H22119.00
C8—C7—H7119.00C22—C23—H23121.00
N2—C7—H7119.00C24—C23—H23121.00
C8—C9—H9119.00C24—C25—H25120.00
C10—C9—H9119.00C26—C25—H25120.00
C11—C10—H10120.00C21—C26—H26120.00
C9—C10—H10120.00C25—C26—H26120.00
C1—N1—N2—C7172.3 (3)C9—C10—C11—C122.5 (6)
N2—N1—C1—C210.7 (5)C10—C11—C12—C13−2.2 (7)
N2—N1—C1—C6−171.1 (3)Cl1—C11—C12—C13177.8 (4)
N1—N2—C7—C8179.6 (3)C11—C12—C13—C80.3 (7)
N4—N3—C14—C19−178.2 (3)N3—C14—C15—C16179.9 (3)
C14—N3—N4—C20−178.2 (3)C19—C14—C15—C16−0.5 (5)
N4—N3—C14—C151.4 (5)N3—C14—C19—C18179.7 (3)
N3—N4—C20—C21−179.8 (3)C15—C14—C19—C180.0 (5)
N1—C1—C2—C3178.2 (4)C14—C15—C16—C170.1 (6)
N1—C1—C6—C5−179.3 (4)C15—C16—C17—C180.7 (6)
C2—C1—C6—C5−1.0 (6)C16—C17—C18—C19−1.1 (6)
C6—C1—C2—C3−0.1 (6)C17—C18—C19—C140.8 (6)
C1—C2—C3—C40.2 (6)N4—C20—C21—C22179.3 (3)
C2—C3—C4—C50.8 (6)N4—C20—C21—C26−0.5 (5)
C3—C4—C5—C6−1.9 (6)C20—C21—C22—C23179.7 (3)
C4—C5—C6—C12.0 (6)C26—C21—C22—C23−0.6 (5)
N2—C7—C8—C13170.3 (4)C20—C21—C26—C25−178.8 (3)
N2—C7—C8—C9−8.9 (6)C22—C21—C26—C251.4 (5)
C13—C8—C9—C10−0.9 (6)C21—C22—C23—C240.7 (6)
C7—C8—C13—C12−178.0 (4)C22—C23—C24—Cl2177.7 (3)
C7—C8—C9—C10178.3 (4)C22—C23—C24—C25−1.6 (6)
C9—C8—C13—C121.3 (6)Cl2—C24—C25—C26−176.9 (3)
C8—C9—C10—C11−1.0 (6)C23—C24—C25—C262.5 (6)
C9—C10—C11—Cl1−177.5 (3)C24—C25—C26—C21−2.4 (6)
Cg1 and Cg2 are the centroids of the C14–C19 and C1–C6 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C10—H10···Cg1i0.932.913.668 (4)139
C20—H20···Cg2ii0.932.733.660 (4)174
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C14–C19 and C1–C6 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C10—H10⋯Cg1i0.932.913.668 (4)139
C20—H20⋯Cg2ii0.932.733.660 (4)174

Symmetry codes: (i) ; (ii) .

  4 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  (E)-1-(2-Nitro-benzyl-idene)-2-phenyl-hydrazine.

Authors:  Hazoor Ahmad Shad; M Nawaz Tahir; Muhammad Ilyas Tariq; Muhammad Sarfraz; Shahbaz Ahmad
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-07

3.  (E)-1-(4-Meth-oxy-benzyl-idene)-2-phenyl-hydrazine.

Authors:  Muhammad Mufakkar; M Nawaz Tahir; Muhammad Ilyas Tariq; Shahbaz Ahmad; Muhammad Sarfraz
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-03

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total
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1.  Crystal structure and Hirshfeld surface analysis of methyl 4-[(E)-2-(5-bromo-2-meth-oxy-benzyl-idene)hydrazin-yl]-3-nitro-benzoate.

Authors:  Tanvirbanu J Malek; Sahaj A Gandhi; Vijay Barot; Mukesh Patel; Urmila H Patel
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-08-14
  1 in total

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