Literature DB >> 21523009

8-[(Hydrazinyl-idene)meth-yl]-4-methyl-2-oxo-2H-chromen-7-yl 4-methyl-benzene-sulfonate.

H Yuvaraj, D Gayathri, Rajesh G Kalkhambkar, G M Kulkarni, Rajendra M Bapset.   

Abstract

In the title compound, C(18)H(16)N(2)O(5)S, the coumarin ring system is nearly planar, with a maximum out-of-plane deviation of 0.078 (1) Å (r.m.s. deviation = 0.046 Å). The dihedral angle between the coumarin ring system and the toluene ring (r.m.s. deviation = 0.004 Å) is 2.77 (1)°. The crystal packing is stabilized by C-H⋯O and N-H⋯O inter-molecular hydrogen bonds generating C(8), C(9) and C(11) chains and R(2) (2)(14), R(2) (2)(23) and R(4) (3)(13) ring graph sets.

Entities:  

Year:  2011        PMID： 21523009      PMCID： PMC3051468          DOI： 10.1107/S1600536810054620

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


Related literature

For the biological activity of coumarins, see: Kulkarni et al. (2006 ▶); Kalkhambkar et al. (2008 ▶); Laakso et al. (1994 ▶); Nofal et al. (2000 ▶). For related structures, see: Kokila et al. (1995 ▶); Vasudevan et al. (1990 ▶). For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H16N2O5S M = 372.39 Monoclinic, a = 9.1947 (3) Å b = 16.1867 (4) Å c = 11.6538 (3) Å β = 99.670 (1)° V = 1709.81 (8) Å3 Z = 4 Mo Kα radiation μ = 0.22 mm−1 T = 293 K 0.2 × 0.19 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer 26334 measured reflections 4260 independent reflections 3285 reflections with I > 2σ(I) R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.116 S = 1.04 4260 reflections 237 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.40 e Å−3 Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PARST (Nardelli, 1995 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054620/si2319sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810054620/si2319Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H16N2O5SF(000) = 776
Mr = 372.39Dx = 1.447 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7131 reflections
a = 9.1947 (3) Åθ = 2.2–27.3°
b = 16.1867 (4) ŵ = 0.22 mm−1
c = 11.6538 (3) ÅT = 293 K
β = 99.670 (1)°Plate, colorless
V = 1709.81 (8) Å30.2 × 0.19 × 0.19 mm
Z = 4
Bruker SMART CCD area-detector diffractometer3285 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.033
graphiteθmax = 28.3°, θmin = 2.2°
phi and ω scansh = −12→12
26334 measured reflectionsk = −21→21
4260 independent reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0548P)2 + 0.5733P] where P = (Fo2 + 2Fc2)/3
4260 reflections(Δ/σ)max = 0.001
237 parametersΔρmax = 0.35 e Å−3
0 restraintsΔρmin = −0.40 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.
xyzUiso*/Ueq
S10.87241 (5)0.20073 (3)0.74789 (4)0.04805 (14)
O20.40215 (11)−0.02903 (6)0.69872 (10)0.0400 (3)
O30.83056 (11)0.12613 (6)0.65832 (10)0.0381 (3)
O10.21065 (13)−0.09419 (7)0.74469 (14)0.0591 (4)
O40.78108 (16)0.19431 (11)0.83435 (14)0.0793 (5)
O50.86864 (16)0.27548 (8)0.68331 (17)0.0777 (5)
C110.70098 (16)−0.02353 (9)0.74255 (14)0.0371 (3)
H110.6508−0.05990.78370.045*
C70.61790 (16)0.04122 (9)0.67270 (13)0.0330 (3)
C80.67779 (16)0.11089 (9)0.62748 (13)0.0357 (3)
C50.37380 (16)0.09308 (9)0.57881 (13)0.0355 (3)
C60.46285 (16)0.03608 (9)0.64762 (13)0.0331 (3)
C121.05418 (18)0.17468 (10)0.80513 (14)0.0409 (4)
C171.3108 (2)0.20553 (11)0.83220 (17)0.0488 (4)
H171.38760.23920.81750.059*
C20.15966 (17)0.02146 (10)0.62033 (15)0.0416 (4)
H20.05780.01610.61270.050*
C90.59404 (19)0.16704 (11)0.55527 (15)0.0457 (4)
H90.63940.21070.52340.055*
C10.25173 (17)−0.03775 (10)0.69100 (16)0.0417 (4)
C40.11620 (19)0.14562 (12)0.49470 (15)0.0484 (4)
H4A0.01500.13160.49580.073*
H4B0.13420.14510.41590.073*
H4C0.13630.19970.52720.073*
C30.21464 (17)0.08395 (10)0.56514 (14)0.0377 (3)
C100.44325 (19)0.15798 (11)0.53077 (15)0.0460 (4)
H100.38700.19550.48170.055*
C181.16766 (19)0.22511 (11)0.78238 (16)0.0453 (4)
H181.14800.27120.73460.054*
C141.2259 (2)0.08804 (12)0.92495 (17)0.0524 (4)
H141.24540.04190.97250.063*
C131.0825 (2)0.10645 (12)0.87741 (16)0.0500 (4)
H131.00540.07360.89350.060*
C151.34283 (19)0.13723 (11)0.90328 (16)0.0468 (4)
C161.4988 (2)0.11716 (14)0.9572 (2)0.0643 (5)
H16A1.56400.15830.93510.096*
H16B1.52510.06400.93060.096*
H16C1.50700.11641.04040.096*
N10.83982 (14)−0.03170 (8)0.74886 (13)0.0411 (3)
N20.90695 (16)−0.09370 (10)0.81607 (14)0.0519 (4)
H2A0.8559−0.12580.85260.062*
H2B1.0006−0.10090.82220.062*
U11U22U33U12U13U23
S10.0384 (2)0.0402 (2)0.0663 (3)−0.00432 (16)0.01104 (19)−0.01826 (19)
O20.0273 (5)0.0324 (5)0.0604 (7)0.0000 (4)0.0079 (5)0.0048 (5)
O30.0329 (5)0.0358 (6)0.0473 (6)−0.0059 (4)0.0112 (4)−0.0073 (5)
O10.0357 (6)0.0406 (7)0.1039 (11)−0.0001 (5)0.0202 (7)0.0154 (7)
O40.0507 (8)0.1124 (13)0.0803 (10)−0.0143 (8)0.0272 (8)−0.0508 (10)
O50.0566 (9)0.0329 (7)0.1361 (15)−0.0016 (6)−0.0055 (9)0.0022 (8)
C110.0309 (7)0.0354 (8)0.0459 (8)−0.0009 (6)0.0084 (6)0.0008 (6)
C70.0311 (7)0.0332 (7)0.0355 (7)−0.0003 (5)0.0076 (6)−0.0050 (6)
C80.0311 (7)0.0372 (7)0.0397 (8)−0.0035 (6)0.0084 (6)−0.0034 (6)
C50.0339 (7)0.0374 (8)0.0352 (7)0.0020 (6)0.0052 (6)−0.0027 (6)
C60.0322 (7)0.0306 (7)0.0374 (7)−0.0006 (5)0.0085 (6)−0.0039 (6)
C120.0398 (8)0.0394 (8)0.0445 (8)−0.0087 (6)0.0099 (7)−0.0108 (7)
C170.0415 (9)0.0480 (9)0.0580 (10)−0.0150 (7)0.0116 (8)−0.0064 (8)
C20.0280 (7)0.0410 (8)0.0547 (10)0.0021 (6)0.0036 (7)−0.0080 (7)
C90.0455 (9)0.0460 (9)0.0467 (9)−0.0046 (7)0.0107 (7)0.0116 (7)
C10.0297 (7)0.0334 (8)0.0632 (10)−0.0006 (6)0.0113 (7)−0.0047 (7)
C40.0412 (9)0.0561 (10)0.0459 (9)0.0102 (8)0.0012 (7)0.0019 (8)
C30.0340 (7)0.0396 (8)0.0381 (8)0.0050 (6)0.0024 (6)−0.0083 (6)
C100.0442 (9)0.0485 (10)0.0442 (9)0.0033 (7)0.0040 (7)0.0109 (7)
C180.0466 (9)0.0379 (8)0.0518 (10)−0.0106 (7)0.0093 (7)−0.0047 (7)
C140.0549 (11)0.0502 (10)0.0505 (10)−0.0092 (8)0.0040 (8)0.0042 (8)
C130.0498 (10)0.0508 (10)0.0505 (10)−0.0173 (8)0.0116 (8)−0.0010 (8)
C150.0433 (9)0.0492 (10)0.0481 (9)−0.0063 (7)0.0079 (7)−0.0097 (7)
C160.0479 (11)0.0686 (13)0.0739 (14)−0.0012 (9)0.0030 (10)−0.0027 (11)
N10.0321 (6)0.0398 (7)0.0513 (8)0.0020 (5)0.0070 (6)0.0035 (6)
N20.0338 (7)0.0548 (9)0.0668 (10)0.0064 (6)0.0074 (7)0.0177 (7)
S1—O41.4197 (15)C2—C31.342 (2)
S1—O51.4222 (16)C2—C11.442 (2)
S1—O31.6003 (11)C2—H20.9300
S1—C121.7441 (17)C9—C101.376 (2)
O2—C61.3742 (18)C9—H90.9300
O2—C11.3781 (18)C4—C31.497 (2)
O3—C81.4119 (18)C4—H4A0.9600
O1—C11.203 (2)C4—H4B0.9600
C11—N11.2732 (19)C4—H4C0.9600
C11—C71.461 (2)C10—H100.9300
C11—H110.9300C18—H180.9300
C7—C81.397 (2)C14—C131.374 (3)
C7—C61.409 (2)C14—C151.395 (2)
C8—C91.382 (2)C14—H140.9300
C5—C61.394 (2)C13—H130.9300
C5—C101.395 (2)C15—C161.501 (3)
C5—C31.453 (2)C16—H16A0.9600
C12—C181.385 (2)C16—H16B0.9600
C12—C131.387 (2)C16—H16C0.9600
C17—C151.383 (3)N1—N21.3561 (19)
C17—C181.384 (3)N2—H2A0.8600
C17—H170.9300N2—H2B0.8600
O4—S1—O5118.24 (11)O1—C1—C2126.59 (15)
O4—S1—O3107.55 (8)O2—C1—C2117.10 (14)
O5—S1—O3108.36 (9)C3—C4—H4A109.5
O4—S1—C12110.73 (10)C3—C4—H4B109.5
O5—S1—C12110.17 (9)H4A—C4—H4B109.5
O3—S1—C12100.20 (7)C3—C4—H4C109.5
C6—O2—C1121.77 (12)H4A—C4—H4C109.5
C8—O3—S1114.70 (9)H4B—C4—H4C109.5
N1—C11—C7122.14 (14)C2—C3—C5118.53 (14)
N1—C11—H11118.9C2—C3—C4121.58 (15)
C7—C11—H11118.9C5—C3—C4119.84 (15)
C8—C7—C6114.76 (13)C9—C10—C5120.70 (15)
C8—C7—C11125.94 (13)C9—C10—H10119.7
C6—C7—C11119.30 (13)C5—C10—H10119.7
C9—C8—C7123.11 (14)C17—C18—C12118.61 (17)
C9—C8—O3117.97 (13)C17—C18—H18120.7
C7—C8—O3118.91 (13)C12—C18—H18120.7
C6—C5—C10117.71 (14)C13—C14—C15121.31 (18)
C6—C5—C3118.63 (14)C13—C14—H14119.3
C10—C5—C3123.60 (14)C15—C14—H14119.3
O2—C6—C5120.98 (13)C14—C13—C12119.15 (16)
O2—C6—C7115.20 (13)C14—C13—H13120.4
C5—C6—C7123.80 (14)C12—C13—H13120.4
C18—C12—C13121.00 (16)C17—C15—C14118.17 (17)
C18—C12—S1119.25 (14)C17—C15—C16121.05 (17)
C13—C12—S1119.67 (13)C14—C15—C16120.78 (18)
C15—C17—C18121.75 (16)C15—C16—H16A109.5
C15—C17—H17119.1C15—C16—H16B109.5
C18—C17—H17119.1H16A—C16—H16B109.5
C3—C2—C1122.85 (14)C15—C16—H16C109.5
C3—C2—H2118.6H16A—C16—H16C109.5
C1—C2—H2118.6H16B—C16—H16C109.5
C10—C9—C8119.70 (15)C11—N1—N2117.71 (14)
C10—C9—H9120.2N1—N2—H2A120.0
C8—C9—H9120.2N1—N2—H2B120.0
O1—C1—O2116.30 (15)H2A—N2—H2B120.0
O4—S1—O3—C842.38 (14)C7—C8—C9—C103.9 (3)
O5—S1—O3—C8−86.51 (12)O3—C8—C9—C10−174.80 (15)
C12—S1—O3—C8158.10 (11)C6—O2—C1—O1−175.70 (15)
N1—C11—C7—C8−15.2 (2)C6—O2—C1—C24.0 (2)
N1—C11—C7—C6165.64 (15)C3—C2—C1—O1178.45 (18)
C6—C7—C8—C9−5.4 (2)C3—C2—C1—O2−1.2 (2)
C11—C7—C8—C9175.39 (15)C1—C2—C3—C5−1.0 (2)
C6—C7—C8—O3173.29 (13)C1—C2—C3—C4−178.52 (15)
C11—C7—C8—O3−5.9 (2)C6—C5—C3—C20.7 (2)
S1—O3—C8—C972.10 (16)C10—C5—C3—C2−176.51 (16)
S1—O3—C8—C7−106.67 (13)C6—C5—C3—C4178.20 (14)
C1—O2—C6—C5−4.5 (2)C10—C5—C3—C41.0 (2)
C1—O2—C6—C7173.91 (13)C8—C9—C10—C50.5 (3)
C10—C5—C6—O2179.38 (14)C6—C5—C10—C9−2.9 (2)
C3—C5—C6—O22.0 (2)C3—C5—C10—C9174.32 (16)
C10—C5—C6—C71.1 (2)C15—C17—C18—C120.2 (3)
C3—C5—C6—C7−176.24 (14)C13—C12—C18—C170.8 (3)
C8—C7—C6—O2−175.49 (13)S1—C12—C18—C17177.42 (13)
C11—C7—C6—O23.8 (2)C15—C14—C13—C121.0 (3)
C8—C7—C6—C52.9 (2)C18—C12—C13—C14−1.3 (3)
C11—C7—C6—C5−177.88 (14)S1—C12—C13—C14−177.96 (14)
O4—S1—C12—C18−133.39 (14)C18—C17—C15—C14−0.5 (3)
O5—S1—C12—C18−0.71 (17)C18—C17—C15—C16−179.64 (18)
O3—S1—C12—C18113.30 (14)C13—C14—C15—C170.0 (3)
O4—S1—C12—C1343.30 (17)C13—C14—C15—C16179.07 (19)
O5—S1—C12—C13175.97 (14)C7—C11—N1—N2179.96 (14)
O3—S1—C12—C13−70.01 (14)
D—H···AD—HH···AD···AD—H···A
N2—H2A···O5i0.862.593.303 (2)141
N2—H2B···O1ii0.862.273.045 (2)150
C10—H10···O4iii0.932.553.469 (2)169
C16—H16A···O4ii0.962.553.405 (3)149
C18—H18···O1iv0.932.533.166 (2)126
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N2—H2A⋯O5i0.862.593.303 (2)141
N2—H2B⋯O1ii0.862.273.045 (2)150
C10—H10⋯O4iii0.932.553.469 (2)169
C16—H16A⋯O4ii0.962.553.405 (3)149
C18—H18⋯O1iv0.932.533.166 (2)126

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

  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

Review 2.  Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents.

Authors:  Manohar V Kulkarni; Geeta M Kulkarni; Chao-Hsiung Lin; Chung-Ming Sun
Journal:  Curr Med Chem       Date:  2006       Impact factor: 4.530

3.  Synthesis and biological activities of some new fluorinated coumarins and 1-aza coumarins.

Authors:  Rajesh G Kalkhambkar; Geeta M Kulkarni; Chandrappa M Kamanavalli; N Premkumar; S M B Asdaq; Chung Ming Sun
Journal:  Eur J Med Chem       Date:  2007-09-11       Impact factor: 6.514

4.  Isokotanins A-C: new bicoumarins from the sclerotia of Aspergillus alliaceus.

Authors:  J A Laakso; E D Narske; J B Gloer; D T Wicklow; P F Dowd
Journal:  J Nat Prod       Date:  1994-01       Impact factor: 4.050

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.  8-Formyl-4-methyl-2-oxo-2H-chromen-7-yl 4-methyl-benzenesulfonate.

Authors:  H Yuvaraj; D Gayathri; Rajesh G Kalkhambkar; Geeta M Kulkarni; Rajendra M Bapset
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-05-25
  1 in total

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