Literature DB >> 21754027

(E)-6-Bromo-3-{2-[2-(4-chloro-benzyl-idene)hydrazin-yl]thia-zol-5-yl}-2H-chromen-2-one.

Afsheen Arshad, Hasnah Osman, Chan Kit Lam, Madhukar Hemamalini, Hoong-Kun Fun.   

Abstract

In the title compound, C(19)H(11)N(3)O(2)SClBr, the chromene ring system and the thia-zole ring are each approximately planar, with maximum deviations of 0.033 (3) Å and 0.006 (3) Å, respectively. The mol-ecule adopts an E configuration about the central C=N double bond. The central thia-zole ring makes dihedral angles of 9.06 (14)° and 12.07 (11)° with the chloro-substituted phenyl ring and the chromene ring, respectively. The mol-ecular structure features a short C-H⋯O contact, which generates an S(6) ring motif. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds, which link the mol-ecules into chains along the b axis. π-π stacking inter-actions [centroid-centroid distance = 3.4813 (15) Å] are also present.

Entities:  

Year:  2011        PMID： 21754027      PMCID： PMC3099884          DOI： 10.1107/S1600536811011172

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


Related literature

For the biological activity and applications of thia­zolyl coumarin derivatives, see: Samsonova et al. (2007 ▶); Bullock et al. (2009 ▶); Siddiqui et al. (2009 ▶); Kalkhambkar et al. (2007 ▶); Kamal et al. (2009 ▶); Desai et al. (2008 ▶). For the synthesis of the title compound, see: Bakkar et al. (2003 ▶); Vijesh et al. (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C19H11BrClN3O2S M = 460.73 Monoclinic, a = 30.5837 (7) Å b = 13.6682 (3) Å c = 9.0454 (1) Å β = 90.161 (2)° V = 3781.18 (13) Å3 Z = 8 Mo Kα radiation μ = 2.45 mm−1 T = 296 K 0.21 × 0.16 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.628, T max = 0.842 29664 measured reflections 5499 independent reflections 2216 reflections with I > 2σ(I) R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.138 S = 0.97 5499 reflections 248 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.31 e Å−3 Δρmin = −0.34 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 datablocks global, I. DOI: 10.1107/S1600536811011172/sj5122sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011172/sj5122Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H11BrClN3O2SF(000) = 1840
Mr = 460.73Dx = 1.619 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3684 reflections
a = 30.5837 (7) Åθ = 2.5–23.1°
b = 13.6682 (3) ŵ = 2.45 mm−1
c = 9.0454 (1) ÅT = 296 K
β = 90.161 (2)°Block, yellow
V = 3781.18 (13) Å30.21 × 0.16 × 0.07 mm
Z = 8
Bruker SMART APEXII CCD area-detector diffractometer5499 independent reflections
Radiation source: fine-focus sealed tube2216 reflections with I > 2σ(I)
graphiteRint = 0.058
φ and ω scansθmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −40→42
Tmin = 0.628, Tmax = 0.842k = −19→19
29664 measured reflectionsl = −12→12
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 0.97w = 1/[σ2(Fo2) + (0.0551P)2 + 0.960P] where P = (Fo2 + 2Fc2)/3
5499 reflections(Δ/σ)max = 0.001
248 parametersΔρmax = 0.31 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br10.437955 (16)0.51731 (4)1.13651 (6)0.1287 (3)
Cl1−0.00680 (3)0.31602 (10)−0.05275 (11)0.1132 (4)
S10.19723 (3)0.13873 (7)0.60268 (9)0.0712 (3)
O10.33937 (7)0.13971 (15)1.0762 (2)0.0679 (6)
O20.29214 (8)0.04381 (19)0.9684 (3)0.0902 (7)
N10.23951 (7)0.28268 (18)0.7199 (2)0.0575 (6)
N20.18701 (9)0.3330 (2)0.5513 (3)0.0698 (8)
N30.15428 (8)0.3072 (2)0.4558 (2)0.0629 (7)
C10.41549 (11)0.3221 (3)1.2104 (4)0.0778 (10)
H1A0.43810.32731.27900.093*
C20.39334 (10)0.2362 (3)1.1954 (3)0.0738 (9)
H2A0.40090.18251.25330.089*
C30.35967 (9)0.2291 (2)1.0938 (3)0.0609 (8)
C40.30642 (10)0.1259 (3)0.9763 (3)0.0652 (8)
C50.29156 (9)0.2090 (2)0.8891 (3)0.0556 (7)
C60.31145 (9)0.2961 (2)0.9077 (3)0.0591 (8)
H6A0.30180.34930.85240.071*
C70.34686 (9)0.3096 (2)1.0094 (3)0.0601 (8)
C80.36987 (9)0.3966 (3)1.0262 (4)0.0715 (9)
H8A0.36200.45150.97160.086*
C90.40440 (10)0.4013 (3)1.1240 (4)0.0766 (10)
C100.25573 (9)0.1967 (2)0.7827 (3)0.0569 (7)
C110.23679 (10)0.1131 (2)0.7328 (3)0.0662 (8)
H11A0.24420.05050.76450.079*
C120.20879 (9)0.2616 (2)0.6261 (3)0.0583 (8)
C130.13768 (10)0.3778 (3)0.3809 (3)0.0666 (8)
H13A0.14860.44080.39350.080*
C140.10205 (10)0.3614 (2)0.2765 (3)0.0609 (8)
C150.08312 (10)0.2710 (3)0.2569 (3)0.0713 (9)
H15A0.09310.21830.31280.086*
C160.04983 (10)0.2566 (3)0.1567 (3)0.0763 (10)
H16A0.03770.19480.14400.092*
C170.03487 (10)0.3341 (3)0.0762 (3)0.0767 (10)
C180.05284 (12)0.4249 (3)0.0907 (4)0.0925 (12)
H18A0.04260.47710.03440.111*
C190.08655 (11)0.4378 (3)0.1909 (4)0.0846 (10)
H19A0.09910.49940.20100.102*
H1N20.1963 (12)0.388 (3)0.547 (4)0.092 (14)*
U11U22U33U12U13U23
Br10.1122 (4)0.0915 (4)0.1821 (5)−0.0164 (3)−0.0729 (4)−0.0212 (3)
Cl10.0812 (6)0.1664 (12)0.0917 (6)0.0210 (7)−0.0463 (5)−0.0255 (7)
S10.0712 (5)0.0676 (6)0.0748 (5)−0.0092 (4)−0.0221 (4)−0.0101 (4)
O10.0663 (13)0.0633 (15)0.0739 (13)0.0083 (11)−0.0199 (11)0.0053 (11)
O20.0935 (17)0.0603 (16)0.1165 (19)−0.0022 (14)−0.0368 (14)0.0108 (15)
N10.0574 (14)0.0579 (16)0.0572 (13)0.0024 (12)−0.0134 (12)−0.0054 (12)
N20.0731 (18)0.065 (2)0.0715 (17)−0.0067 (16)−0.0335 (14)−0.0020 (16)
N30.0618 (15)0.0675 (18)0.0593 (14)−0.0034 (13)−0.0222 (12)−0.0035 (13)
C10.062 (2)0.092 (3)0.079 (2)0.012 (2)−0.0280 (17)−0.015 (2)
C20.071 (2)0.078 (2)0.073 (2)0.0179 (19)−0.0248 (17)0.0020 (19)
C30.0561 (17)0.064 (2)0.0623 (18)0.0080 (16)−0.0080 (15)−0.0052 (16)
C40.0615 (19)0.059 (2)0.075 (2)0.0033 (17)−0.0123 (16)0.0000 (18)
C50.0544 (16)0.057 (2)0.0556 (16)0.0079 (15)−0.0070 (13)−0.0087 (15)
C60.0574 (17)0.0558 (19)0.0639 (17)0.0043 (15)−0.0139 (14)−0.0037 (15)
C70.0523 (16)0.064 (2)0.0638 (18)0.0106 (15)−0.0140 (14)−0.0096 (16)
C80.0622 (19)0.063 (2)0.089 (2)0.0099 (17)−0.0253 (17)−0.0119 (19)
C90.066 (2)0.073 (2)0.091 (2)0.0052 (18)−0.0242 (18)−0.022 (2)
C100.0553 (17)0.058 (2)0.0577 (17)0.0031 (15)−0.0051 (14)−0.0033 (15)
C110.0664 (19)0.058 (2)0.074 (2)0.0010 (16)−0.0174 (16)−0.0036 (17)
C120.0579 (17)0.064 (2)0.0535 (16)0.0003 (15)−0.0114 (14)−0.0064 (15)
C130.0686 (19)0.068 (2)0.0634 (18)−0.0012 (17)−0.0199 (16)−0.0117 (17)
C140.0605 (18)0.063 (2)0.0592 (17)0.0073 (16)−0.0150 (15)−0.0078 (16)
C150.0673 (19)0.078 (2)0.0688 (19)0.0023 (18)−0.0228 (16)−0.0028 (18)
C160.066 (2)0.085 (3)0.078 (2)−0.0002 (19)−0.0202 (17)−0.011 (2)
C170.061 (2)0.106 (3)0.0624 (19)0.017 (2)−0.0232 (16)−0.015 (2)
C180.095 (3)0.095 (3)0.088 (3)0.025 (2)−0.037 (2)0.005 (2)
C190.089 (2)0.074 (2)0.090 (2)0.009 (2)−0.032 (2)−0.004 (2)
Br1—C91.892 (3)C5—C101.466 (4)
Cl1—C171.743 (3)C6—C71.431 (4)
S1—C111.721 (3)C6—H6A0.9300
S1—C121.728 (3)C7—C81.390 (4)
O1—C41.365 (4)C8—C91.377 (4)
O1—C31.379 (4)C8—H8A0.9300
O2—C41.206 (4)C10—C111.359 (4)
N1—C121.297 (3)C11—H11A0.9300
N1—C101.395 (4)C13—C141.458 (4)
N2—C121.361 (4)C13—H13A0.9300
N2—N31.366 (3)C14—C151.376 (4)
N2—H1N20.81 (4)C14—C191.383 (4)
N3—C131.283 (4)C15—C161.376 (4)
C1—C21.363 (5)C15—H15A0.9300
C1—C91.377 (5)C16—C171.364 (5)
C1—H1A0.9300C16—H16A0.9300
C2—C31.382 (4)C17—C181.363 (5)
C2—H2A0.9300C18—C191.382 (5)
C3—C71.395 (4)C18—H18A0.9300
C4—C51.455 (4)C19—H19A0.9300
C5—C61.347 (4)
C11—S1—C1288.34 (15)C1—C9—Br1119.5 (2)
C4—O1—C3122.0 (2)C8—C9—Br1119.5 (3)
C12—N1—C10109.6 (2)C11—C10—N1115.0 (2)
C12—N2—N3119.1 (3)C11—C10—C5129.2 (3)
C12—N2—H1N2122 (3)N1—C10—C5115.8 (3)
N3—N2—H1N2118 (3)C10—C11—S1110.7 (2)
C13—N3—N2115.4 (3)C10—C11—H11A124.6
C2—C1—C9120.0 (3)S1—C11—H11A124.6
C2—C1—H1A120.0N1—C12—N2121.2 (3)
C9—C1—H1A120.0N1—C12—S1116.4 (2)
C1—C2—C3119.7 (3)N2—C12—S1122.4 (2)
C1—C2—H2A120.1N3—C13—C14121.3 (3)
C3—C2—H2A120.1N3—C13—H13A119.3
O1—C3—C2118.3 (3)C14—C13—H13A119.3
O1—C3—C7120.6 (2)C15—C14—C19117.6 (3)
C2—C3—C7121.1 (3)C15—C14—C13122.4 (3)
O2—C4—O1115.7 (3)C19—C14—C13120.0 (3)
O2—C4—C5125.6 (3)C16—C15—C14121.6 (3)
O1—C4—C5118.7 (3)C16—C15—H15A119.2
C6—C5—C4118.8 (3)C14—C15—H15A119.2
C6—C5—C10121.3 (3)C17—C16—C15119.2 (3)
C4—C5—C10119.9 (3)C17—C16—H16A120.4
C5—C6—C7122.3 (3)C15—C16—H16A120.4
C5—C6—H6A118.8C18—C17—C16121.4 (3)
C7—C6—H6A118.8C18—C17—Cl1119.2 (3)
C8—C7—C3118.3 (3)C16—C17—Cl1119.4 (3)
C8—C7—C6124.2 (3)C17—C18—C19118.6 (4)
C3—C7—C6117.5 (3)C17—C18—H18A120.7
C9—C8—C7119.8 (3)C19—C18—H18A120.7
C9—C8—H8A120.1C18—C19—C14121.6 (4)
C7—C8—H8A120.1C18—C19—H19A119.2
C1—C9—C8121.0 (3)C14—C19—H19A119.2
C12—N2—N3—C13−174.7 (3)C12—N1—C10—C5178.7 (2)
C9—C1—C2—C3−0.3 (5)C6—C5—C10—C11168.5 (3)
C4—O1—C3—C2−178.7 (3)C4—C5—C10—C11−11.1 (5)
C4—O1—C3—C70.3 (4)C6—C5—C10—N1−9.3 (4)
C1—C2—C3—O1176.8 (3)C4—C5—C10—N1171.1 (3)
C1—C2—C3—C7−2.2 (5)N1—C10—C11—S10.1 (3)
C3—O1—C4—O2178.1 (3)C5—C10—C11—S1−177.7 (2)
C3—O1—C4—C5−1.8 (4)C12—S1—C11—C10−0.5 (2)
O2—C4—C5—C6−178.4 (3)C10—N1—C12—N2178.9 (3)
O1—C4—C5—C61.4 (4)C10—N1—C12—S1−1.0 (3)
O2—C4—C5—C101.2 (5)N3—N2—C12—N1−178.7 (3)
O1—C4—C5—C10−179.0 (3)N3—N2—C12—S11.2 (4)
C4—C5—C6—C70.4 (4)C11—S1—C12—N10.9 (2)
C10—C5—C6—C7−179.2 (3)C11—S1—C12—N2−179.0 (3)
O1—C3—C7—C8−176.8 (3)N2—N3—C13—C14−179.1 (3)
C2—C3—C7—C82.2 (4)N3—C13—C14—C152.8 (5)
O1—C3—C7—C61.5 (4)N3—C13—C14—C19−176.2 (3)
C2—C3—C7—C6−179.5 (3)C19—C14—C15—C16−0.3 (5)
C5—C6—C7—C8176.3 (3)C13—C14—C15—C16−179.3 (3)
C5—C6—C7—C3−1.9 (4)C14—C15—C16—C17−0.8 (5)
C3—C7—C8—C90.3 (5)C15—C16—C17—C181.4 (5)
C6—C7—C8—C9−177.9 (3)C15—C16—C17—Cl1179.1 (2)
C2—C1—C9—C82.8 (5)C16—C17—C18—C19−0.8 (6)
C2—C1—C9—Br1−175.8 (3)Cl1—C17—C18—C19−178.5 (3)
C7—C8—C9—C1−2.8 (5)C17—C18—C19—C14−0.4 (6)
C7—C8—C9—Br1175.8 (2)C15—C14—C19—C181.0 (5)
C12—N1—C10—C110.6 (4)C13—C14—C19—C18180.0 (3)
D—H···AD—HH···AD···AD—H···A
N2—H1N2···O2i0.81 (4)2.16 (4)2.957 (4)169 (4)
C11—H11A···O20.932.352.878 (4)115
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H1N2⋯O2i0.81 (4)2.16 (4)2.957 (4)169 (4)
C11—H11A⋯O20.932.352.878 (4)115

Symmetry code: (i) .

  5 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.  Synthesis of novel triheterocyclic thiazoles as anti-inflammatory and analgesic agents.

Authors:  R G Kalkhambkar; G M Kulkarni; H Shivkumar; R Nagendra Rao
Journal:  Eur J Med Chem       Date:  2007-01-27       Impact factor: 6.514

3.  Synthesis, characterization and anti-microbial studies of some novel 2,4-disubstituted thiazoles.

Authors:  A M Vijesh; Arun M Isloor; Vivek Prabhu; Shaoib Ahmad; Shridhar Malladi
Journal:  Eur J Med Chem       Date:  2010-08-06       Impact factor: 6.514

4.  Synthesis of some new coumarin incorporated thiazolyl semicarbazones as anticonvulsants.

Authors:  Nadeem Siddiqui; M Faiz Arshad; Suroor A Khan
Journal:  Acta Pol Pharm       Date:  2009 Mar-Apr       Impact factor: 0.330

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  5 in total
  1 in total

1.  (E)-6-Bromo-3-{2-[2-(2-meth-oxy-benzyl-idene)hydrazin-yl]-1,3-thia-zol-4-yl}-2H-chromen-2-one.

Authors:  Afsheen Arshad; Hasnah Osman; Chan Kit Lam; Madhukar Hemamalini; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-25
  1 in total

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