Literature DB >> 21203289

4-Chloro-N'-[(Z)-4-(dimethyl-amino)benzyl-idene]benzohydrazide mono-hydrate.

Hoong-Kun Fun, P S Patil, Samuel Robinson Jebas, K V Sujith, B Kalluraya.   

Abstract

In the title compound, C(16)H(16)ClN(3)O·H(2)O, the dihedral angle between the two aromatic rings is 44.58 (11)°. The N atom of the dimethyl-amino group adopts a pyramidal configuration. In the crystal structure, mol-ecules are linked into a two-dimensional network parallel to the (001) plane by inter-molecular N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds involving the water mol-ecule and C-H⋯Cl hydrogen bonds. In addition, C-H⋯π inter-actions are observed.

Entities:  

Year:  2008        PMID： 21203289      PMCID： PMC2962208          DOI： 10.1107/S1600536808022861

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


Related literature

For the biological activities of hydrazones, see: Bedia et al. (2006 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶); Duraisamy et al. (2008 ▶); Singh et al. (1992 ▶); Ergenç & Günay, (1998 ▶); Durgun et al. (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16ClN3O·H2O M = 319.78 Orthorhombic, a = 6.4418 (1) Å b = 6.9344 (1) Å c = 33.8083 (7) Å V = 1510.22 (4) Å3 Z = 4 Mo Kα radiation μ = 0.26 mm−1 T = 100.0 (1) K 0.32 × 0.16 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.921, T max = 0.981 12336 measured reflections 4311 independent reflections 3301 reflections with I > 2σ(I) R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.050 wR(F 2) = 0.114 S = 1.01 4311 reflections 205 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.34 e Å−3 Δρmin = −0.34 e Å−3 Absolute structure: Flack (1983 ▶), 1724 Friedel pairs Flack parameter: −0.14 (7) Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022861/ci2637sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022861/ci2637Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H16ClN3O·H2OF000 = 672
Mr = 319.78Dx = 1.406 Mg m−3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1906 reflections
a = 6.4418 (1) Åθ = 2.4–23.3º
b = 6.9344 (1) ŵ = 0.26 mm−1
c = 33.8083 (7) ÅT = 100.0 (1) K
V = 1510.22 (4) Å3Needle, colourless
Z = 40.32 × 0.16 × 0.07 mm
Bruker SMART APEXII CCD area-detector diffractometer4311 independent reflections
Radiation source: fine-focus sealed tube3301 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.056
T = 100.0(1) Kθmax = 30.1º
φ and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −9→9
Tmin = 0.921, Tmax = 0.981k = −9→6
12336 measured reflectionsl = −47→37
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.050  w = 1/[σ2(Fo2) + (0.0492P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.114(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.34 e Å−3
4311 reflectionsΔρmin = −0.34 e Å−3
205 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), 1724 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.14 (7)
Secondary atom site location: difference Fourier map
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.
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.
xyzUiso*/Ueq
Cl10.39865 (9)0.50981 (9)0.568340 (15)0.02126 (14)
O1−0.3268 (2)0.4990 (2)0.42597 (4)0.0206 (3)
N1−0.0370 (3)0.4579 (3)0.38853 (5)0.0146 (4)
N2−0.1527 (3)0.4602 (3)0.35420 (5)0.0151 (4)
N3−0.4409 (3)0.4624 (3)0.17091 (5)0.0166 (4)
C1−0.0827 (4)0.4376 (3)0.49549 (6)0.0154 (5)
H1−0.21990.39670.49710.018*
C20.0388 (4)0.4421 (3)0.52925 (6)0.0173 (5)
H2−0.01470.40080.55340.021*
C30.2405 (3)0.5086 (4)0.52666 (6)0.0154 (4)
C40.3243 (4)0.5704 (3)0.49095 (6)0.0157 (5)
H40.45950.61700.48970.019*
C50.2028 (3)0.5613 (3)0.45730 (7)0.0153 (5)
H50.25780.60050.43320.018*
C6−0.0002 (3)0.4943 (4)0.45901 (6)0.0148 (4)
C7−0.1372 (3)0.4843 (3)0.42347 (6)0.0136 (4)
C8−0.0579 (4)0.4106 (3)0.32251 (6)0.0147 (5)
H80.07950.36990.32390.018*
C9−0.1631 (4)0.4172 (3)0.28408 (6)0.0135 (5)
C10−0.0582 (4)0.3550 (3)0.25039 (7)0.0158 (5)
H100.07570.30620.25270.019*
C11−0.1513 (4)0.3651 (3)0.21331 (6)0.0156 (5)
H11−0.07970.32000.19130.019*
C12−0.3506 (4)0.4420 (3)0.20852 (6)0.0152 (5)
C13−0.4564 (3)0.5034 (4)0.24292 (6)0.0160 (4)
H13−0.58970.55380.24080.019*
C14−0.3643 (3)0.4893 (3)0.27960 (6)0.0151 (4)
H14−0.43760.52860.30190.018*
C15−0.6672 (4)0.4541 (4)0.16837 (7)0.0205 (5)
H15A−0.72660.54090.18740.031*
H15B−0.71320.32510.17380.031*
H15C−0.71050.49070.14230.031*
C16−0.3386 (4)0.3595 (4)0.13815 (7)0.0245 (6)
H16A−0.19930.40650.13520.037*
H16B−0.41440.38110.11410.037*
H16C−0.33540.22390.14380.037*
H1N10.0892 (19)0.419 (3)0.3882 (7)0.028 (7)*
O1W0.3779 (3)0.3316 (2)0.37632 (5)0.0259 (4)
H1W10.40930.25940.35730.039*
H2W10.48300.39230.38370.039*
U11U22U33U12U13U23
Cl10.0253 (3)0.0248 (3)0.0137 (3)−0.0021 (3)−0.0051 (2)0.0007 (3)
O10.0130 (7)0.0297 (9)0.0192 (8)0.0003 (7)−0.0006 (6)−0.0030 (8)
N10.0122 (9)0.0197 (11)0.0120 (9)0.0011 (8)−0.0031 (7)−0.0003 (8)
N20.0170 (9)0.0155 (10)0.0127 (9)−0.0013 (7)−0.0028 (7)−0.0004 (7)
N30.0203 (10)0.0189 (11)0.0107 (9)0.0014 (8)−0.0012 (7)−0.0007 (8)
C10.0170 (11)0.0118 (11)0.0174 (11)0.0005 (8)0.0039 (9)−0.0007 (8)
C20.0236 (12)0.0168 (12)0.0117 (11)−0.0016 (9)0.0041 (9)−0.0012 (9)
C30.0221 (11)0.0160 (11)0.0081 (10)0.0016 (10)−0.0016 (8)−0.0010 (10)
C40.0149 (11)0.0166 (12)0.0155 (12)−0.0004 (8)0.0005 (9)−0.0013 (9)
C50.0193 (12)0.0157 (12)0.0110 (11)0.0009 (8)0.0017 (9)−0.0003 (9)
C60.0151 (10)0.0148 (11)0.0144 (10)0.0012 (9)−0.0001 (8)−0.0042 (10)
C70.0170 (10)0.0132 (11)0.0108 (10)−0.0012 (9)0.0007 (8)0.0003 (9)
C80.0124 (10)0.0162 (11)0.0155 (12)−0.0015 (9)−0.0007 (9)0.0006 (9)
C90.0157 (11)0.0128 (11)0.0121 (11)−0.0013 (8)−0.0013 (9)0.0004 (8)
C100.0131 (11)0.0179 (12)0.0164 (12)−0.0009 (9)0.0025 (9)−0.0008 (9)
C110.0166 (11)0.0191 (12)0.0111 (11)−0.0002 (9)0.0025 (9)−0.0030 (9)
C120.0192 (11)0.0127 (11)0.0136 (11)−0.0016 (9)−0.0013 (9)0.0021 (8)
C130.0145 (10)0.0169 (11)0.0167 (11)0.0024 (10)0.0000 (8)−0.0003 (10)
C140.0196 (10)0.0142 (11)0.0116 (10)0.0002 (10)0.0022 (8)−0.0025 (9)
C150.0207 (12)0.0222 (14)0.0186 (12)0.0021 (10)−0.0054 (9)0.0008 (10)
C160.0297 (14)0.0304 (15)0.0134 (12)0.0070 (11)−0.0010 (10)−0.0015 (10)
O1W0.0162 (9)0.0304 (10)0.0310 (10)0.0004 (7)−0.0004 (8)−0.0137 (8)
Cl1—C31.739 (2)C8—C91.466 (3)
O1—C71.229 (2)C8—H80.93
N1—C71.358 (3)C9—C101.393 (3)
N1—N21.379 (2)C9—C141.397 (3)
N1—H1N10.857 (10)C10—C111.391 (3)
N2—C81.280 (3)C10—H100.93
N3—C121.405 (3)C11—C121.400 (3)
N3—C151.461 (3)C11—H110.93
N3—C161.473 (3)C12—C131.414 (3)
C1—C21.384 (3)C13—C141.378 (3)
C1—C61.399 (3)C13—H130.93
C1—H10.93C14—H140.93
C2—C31.382 (3)C15—H15A0.96
C2—H20.93C15—H15B0.96
C3—C41.390 (3)C15—H15C0.96
C4—C51.382 (3)C16—H16A0.96
C4—H40.93C16—H16B0.96
C5—C61.389 (3)C16—H16C0.96
C5—H50.93O1W—H1W10.84
C6—C71.493 (3)O1W—H2W10.83
C7—N1—N2118.25 (17)C10—C9—C14118.2 (2)
C7—N1—H1N1120.4 (17)C10—C9—C8119.4 (2)
N2—N1—H1N1120.3 (17)C14—C9—C8122.4 (2)
C8—N2—N1116.33 (19)C11—C10—C9120.8 (2)
C12—N3—C15117.51 (19)C11—C10—H10119.6
C12—N3—C16116.49 (19)C9—C10—H10119.6
C15—N3—C16112.54 (19)C10—C11—C12121.3 (2)
C2—C1—C6120.4 (2)C10—C11—H11119.4
C2—C1—H1119.8C12—C11—H11119.4
C6—C1—H1119.8C11—C12—N3121.5 (2)
C3—C2—C1119.1 (2)C11—C12—C13117.5 (2)
C3—C2—H2120.4N3—C12—C13121.0 (2)
C1—C2—H2120.4C14—C13—C12120.8 (2)
C2—C3—C4121.5 (2)C14—C13—H13119.6
C2—C3—Cl1120.08 (17)C12—C13—H13119.6
C4—C3—Cl1118.36 (17)C13—C14—C9121.5 (2)
C5—C4—C3118.8 (2)C13—C14—H14119.3
C5—C4—H4120.6C9—C14—H14119.3
C3—C4—H4120.6N3—C15—H15A109.5
C4—C5—C6120.9 (2)N3—C15—H15B109.5
C4—C5—H5119.5H15A—C15—H15B109.5
C6—C5—H5119.5N3—C15—H15C109.5
C5—C6—C1119.2 (2)H15A—C15—H15C109.5
C5—C6—C7122.61 (19)H15B—C15—H15C109.5
C1—C6—C7118.15 (19)N3—C16—H16A109.5
O1—C7—N1122.92 (19)N3—C16—H16B109.5
O1—C7—C6121.92 (18)H16A—C16—H16B109.5
N1—C7—C6115.16 (18)N3—C16—H16C109.5
N2—C8—C9120.9 (2)H16A—C16—H16C109.5
N2—C8—H8119.6H16B—C16—H16C109.5
C9—C8—H8119.6H1W1—O1W—H2W1109.6
C7—N1—N2—C8−171.4 (2)N1—N2—C8—C9−176.96 (18)
C6—C1—C2—C31.9 (3)N2—C8—C9—C10−177.5 (2)
C1—C2—C3—C4−0.2 (4)N2—C8—C9—C144.5 (3)
C1—C2—C3—Cl1−178.32 (17)C14—C9—C10—C110.2 (3)
C2—C3—C4—C5−1.1 (3)C8—C9—C10—C11−177.9 (2)
Cl1—C3—C4—C5176.95 (17)C9—C10—C11—C121.5 (3)
C3—C4—C5—C60.9 (3)C10—C11—C12—N3176.4 (2)
C4—C5—C6—C10.7 (3)C10—C11—C12—C13−1.9 (3)
C4—C5—C6—C7179.3 (2)C15—N3—C12—C11151.7 (2)
C2—C1—C6—C5−2.2 (3)C16—N3—C12—C1113.7 (3)
C2—C1—C6—C7179.2 (2)C15—N3—C12—C13−30.0 (3)
N2—N1—C7—O14.3 (3)C16—N3—C12—C13−168.0 (2)
N2—N1—C7—C6−175.69 (19)C11—C12—C13—C140.7 (3)
C5—C6—C7—O1−151.1 (2)N3—C12—C13—C14−177.7 (2)
C1—C6—C7—O127.4 (3)C12—C13—C14—C91.0 (4)
C5—C6—C7—N128.8 (3)C10—C9—C14—C13−1.5 (3)
C1—C6—C7—N1−152.6 (2)C8—C9—C14—C13176.6 (2)
D—H···AD—HH···AD···AD—H···A
O1W—H1W1···N3i0.842.283.045 (2)152
N1—H1N1···O1W0.86 (1)2.00 (1)2.843 (3)169 (2)
O1W—H2W1···O1ii0.842.022.790 (2)152
O1W—H2W1···N2ii0.842.593.240 (3)135
C15—H15C···Cl1iii0.962.783.704 (2)163
C1—H1···Cg1iv0.932.973.621 (2)128
C4—H4···Cg1v0.932.893.565 (2)130
C10—H10···Cg2vi0.932.873.589 (2)135
C13—H13···Cg2vii0.932.813.497 (3)131
Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1W—H1W1⋯N3i0.842.283.045 (2)152
N1—H1N1⋯O1W0.86 (1)2.00 (1)2.843 (3)169 (2)
O1W—H2W1⋯O1ii0.842.022.790 (2)152
O1W—H2W1⋯N2ii0.842.593.240 (3)135
C15—H15C⋯Cl1iii0.962.783.704 (2)163
C1—H1⋯Cg1iv0.932.973.621 (2)128
C4—H4⋯Cg1v0.932.893.565 (2)130
C10—H10⋯Cg2vi0.932.873.589 (2)135
C13—H13⋯Cg2vii0.932.813.497 (3)131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

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  34 in total

1.  (E)-N'-[1-(4-Bromo-phen-yl)ethyl-idene]-2-hydroxy-benzohydrazide.

Authors:  Chuan-Gang Fan; Ming-Zhi Song
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-17

2.  (E)-4-Hydr-oxy-N'-(4-nitro-benzyl-idene)benzohydrazide.

Authors:  Cong-Ming Li; Hong-Yan Ban
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-06

3.  4-Chloro-N'-(2-hydroxy-benzyl-idene)benzohydrazide monohydrate.

Authors:  Jiu-Fu Lu; Suo-Tian Min; Xiao-Hui Ji; Zhong-Hai Dang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-08-06

4.  N'-[(Z)-4-(Dimethyl-amino)benzyl-idene]-4-nitro-benzohydrazide mono-hydrate.

Authors:  Hoong-Kun Fun; Samuel Robinson Jebas; K V Sujith; P S Patil; B Kalluraya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-09-13

5.  (E)-N'-[1-(4-Bromo-phen-yl)ethyl-idene]benzohydrazide.

Authors:  Hong-Yun Wang; Chuan-Gang Fan; Zhong-Nian Yang
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-12-04

6.  (E)-N'-(2-Furylmethyl-ene)benzo-hydrazide.

Authors:  Ming-Zhi Song; Chuan-Gang Fan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-23

7.  (E)-N'-(5-Bromo-2-methoxy-benzyl-idene)-3-methoxy-benzohydrazide.

Authors:  Cong-Ming Li; Hong-Yan Ban
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-28

8.  (E)-N'-(5-Bromo-2-methoxy-benzyl-idene)-4-methoxy-benzohydrazide.

Authors:  Hong-Yan Ban; Cong-Ming Li
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-08

9.  N'-[4-(Dimethyl-amino)benzyl-idene]-3-hydr-oxy-2-naphthohydrazide.

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Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-03-28

10.  N'-[(Z)-4-Methyl-benzyl-idene]-4-nitro-benzohydrazide monohydrate.

Authors:  Hoong-Kun Fun; Samuel Robinson Jebas; K V Sujith; B Kalluraya
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-11-13
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