Document Detail

3-Hy-droxy-N'-[(E)-2-thienyl-methyl-idene]-2-naphtho-hydrazide.
Jump to Full Text
MedLine Citation:
PMID:  21522969     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
The asymmetric unit of the title compound, C(16)H(12)N(2)O(2)S, contains three independent mol-ecules. Intra-molecular N-H⋯O hydrogen bonds in the three mol-ecules lead to very similar conformations: the thio-pene ring and naphthalene ring system in the three mol-ecules form dihedral angles of 10.3 (2), 9.1 (2) and 9.3 (3)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [031].
Authors:
Qingkun Wu; Handong Yin; Daqi Wang
Related Documents :
21200719 - 2-(4,5-dihydro-1,3-oxazol-2-yl)quinoline.
21163489 - Supramolecular chirality formation of bisazobenzene-substituted polydiacetylene lb films.
21202299 - 2-fluoro-anilinium n-(2-fluoro-phenyl)oxamate.
21406749 - Crystal structure and luminescence properties of liyp(4)o(12):ce(3 + ) phosphor.
9668029 - The molecular structure of morpholine and the morpholine-h2o complex determined by ft m...
21522949 - 2-isobutyl-6-(4-meth-oxy-phen-yl)imidazo[2,1-b][1,3,4]thia-diazole.
17915839 - Connecting structure to infrared spectra of molecular and autodissociated hcl--water ag...
24827779 - Multiple phases of molybdenum carbide as electrocatalysts for the hydrogen evolution re...
23963279 - Nhc to anhc rearrangement by an organotin sulphide cation.
Publication Detail:
Type:  Journal Article     Date:  2011-01-08
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  67     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr Sect E Struct Rep Online     Publication Date:  2011  
Date Detail:
Created Date:  2011-04-27     Completed Date:  2011-07-14     Revised Date:  2013-03-28    
Medline Journal Info:
Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr Sect E Struct Rep Online     Country:  England    
Other Details:
Languages:  eng     Pagination:  o277     Citation Subset:  -    
Affiliation:
College of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, P.R.China.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Comments/Corrections

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

Full Text
Journal Information
Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
Article Information
Download PDF
A full version of this article is available from Crystallography Journals Online.© Wu et al. 2011
open-access:
Received Day: 10 Month: 12 Year: 2010
Accepted Day: 24 Month: 12 Year: 2010
collection publication date: Day: 01 Month: 2 Year: 2011
Electronic publication date: Day: 08 Month: 1 Year: 2011
pmc-release publication date: Day: 08 Month: 1 Year: 2011
Volume: 67 Issue: Pt 2
First Page: o277 Last Page: o277
ID: 3051446
PubMed Id: 21522969
Publisher Id: cv5019
DOI: 10.1107/S160053681005405X
Coden: ACSEBH
Publisher Item Identifier: S160053681005405X

3-Hy­droxy-N′-[(E)-2-thienyl­methyl­idene]-2-naphtho­hydrazide Alternate Title:C16H12N2O2S
Qingkun Wua
Handong Yina*
Daqi Wanga
aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, P.R.China
Correspondence: Correspondence e-mail: handongyin@163.com

Related literature

For related structures, see: Huang (2009); Liang et al. (2008); Shafiq et al. (2009).[Chemical Structure ID: scheme1]


Experimental
Crystal data

  • C16H12N2O2S
  • Mr = 296.34
  • Orthorhombic,
  • a = 19.8191 (16) Å
  • b = 6.2487 (5) Å
  • c = 33.947 (3) Å
  • V = 4204.1 (6) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.24 mm−1
  • T = 298 K
  • 0.41 × 0.17 × 0.06 mm

Data collection

  • Bruker SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.909, Tmax = 0.986
  • 20887 measured reflections
  • 7258 independent reflections
  • 3449 reflections with I > 2σ(I)
  • Rint = 0.077

Refinement

  • R[F2 > 2σ(F2)] = 0.055
  • wR(F2) = 0.078
  • S = 0.97
  • 7258 reflections
  • 569 parameters
  • 11 restraints
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.24 e Å−3
  • Absolute structure: Flack (1983), 3473 Friedel pairs
  • Flack parameter: 0.01 (7)

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.


Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005405X/cv5019sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005405X/cv5019Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5019).

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (grant No. Y2008B48) for financial support.

supplementary crystallographic information
Comment

In continuation of our research of organotin derivatives, the title compound (I) - a novel Schiff base - have been synthesized. Herewith we present its crystal structure.

In (I), there are three independent molecules in the asymmetric unit (Fig. 1). All the bond lengths and angles are normal and correspond to those observed in the related compounds (Huang (2009); Liang et al. (2008); Shafiq et al. (2009). Intramolecular N—H···O hydrogen bonds (Table 1) lead to very close conformations - the thiopene ring and naphthalene bicycle in three molecules form dihedral angles of 9.67 (27)°, 9.16 (29)° and 9.41 (26)°, respectively.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [031].

Experimental

The methanol solution of thiophene(0.1 mol) was added dropwise to a solution of 3-hydroxyl-2-naphthohydrazide(0.1 mol) in mehtanol. Then the mixture was stirred at room temperature for 6 h, during which time a yellow precipitate can be observed. The mixture was filtrated and the obtained solid was recrystallized from methanol. Yield 80%. M.p. 245°C. Anal. Calcd (%) for C16H12N2O2S (Mr = 296.34): C, 64.84; H, 4.08; N, 9.45. Found (%): C, 64.82; H, 4.03; N, 9.49.

Refinement

All H atoms were placed in geometrically idealized positions (C—H=0.93 Å, O—H=0.82 Å, N—H=0.86 Å) and refined using a riding model, with Uiso(H) = 1.2 Ueq(C, O, N).

Figures
Crystal data
Data collection
Refinement
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
Hydrogen-bond geometry (Å, °)

Symmetry codes: (i) −x+1/2, y−3/2, z−1/2.


References
Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Huang, H.-T. (2009). Acta Cryst. E65, o892.
Liang, Q.-F., Feng, H.-M. & Li, F.-Q. (2008). Acta Cryst. E64, o1008.
Shafiq, Z., Yaqub, M., Tahir, M. N., Nawaz, M. H. & Iqbal, M. S. (2009). Acta Cryst. E65, o2845–o2846.
Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Figures

[Figure ID: Fap1]
Fig. 1. 

Three independent molecules of (I) showing the atomic numbering and 50% probability displacement ellipsoids. The hydrogen bonds are shown as dashed lines.



Tables
[TableWrap ID: d1e123]
C16H12N2O2S Dx = 1.405 Mg m3
Mr = 296.34 Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21 Cell parameters from 2181 reflections
a = 19.8191 (16) Å θ = 2.4–26.4°
b = 6.2487 (5) Å µ = 0.24 mm1
c = 33.947 (3) Å T = 298 K
V = 4204.1 (6) Å3 Block, yellow
Z = 12 0.41 × 0.17 × 0.06 mm
F(000) = 1848

[TableWrap ID: d1e248]
Bruker SMART 1000 CCD area-detector diffractometer 7258 independent reflections
Radiation source: fine-focus sealed tube 3449 reflections with I > 2σ(I)
graphite Rint = 0.077
phi and ω scans θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −23→23
Tmin = 0.909, Tmax = 0.986 k = −7→6
20887 measured reflections l = −40→38

[TableWrap ID: d1e363]
Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055 H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0055P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97 (Δ/σ)max < 0.001
7258 reflections Δρmax = 0.28 e Å3
569 parameters Δρmin = −0.24 e Å3
11 restraints Absolute structure: Flack (1983), 3473 Friedel pairs
Primary atom site location: structure-invariant direct methods Flack parameter: 0.01 (7)

[TableWrap ID: d1e524]
x y z Uiso*/Ueq
C17 0.1250 (3) 1.3649 (9) 0.3320 (2) 0.0772 (16)
H17 0.1041 1.4728 0.3465 0.093*
C18 0.1214 (3) 1.3474 (9) 0.2938 (2) 0.0852 (18)
H18 0.0986 1.4477 0.2785 0.102*
C19 0.1535 (2) 1.1707 (8) 0.27682 (17) 0.0632 (15)
H19 0.1533 1.1341 0.2503 0.076*
C20 0.1862 (3) 1.0582 (9) 0.30730 (18) 0.0638 (14)
C21 0.2286 (3) 0.8714 (9) 0.30409 (19) 0.0645 (17)
H21 0.2388 0.8180 0.2792 0.077*
C22 0.3225 (3) 0.4907 (9) 0.35439 (19) 0.0496 (14)
C23 0.3623 (3) 0.2970 (8) 0.34149 (16) 0.0469 (14)
C24 0.3623 (3) 0.2105 (8) 0.30317 (18) 0.0533 (15)
C25 0.3998 (3) 0.0317 (8) 0.29514 (19) 0.0615 (17)
H25 0.3989 −0.0254 0.2698 0.074*
C26 0.4393 (3) −0.0666 (9) 0.32362 (19) 0.0524 (16)
C27 0.4776 (3) −0.2522 (10) 0.3153 (2) 0.076 (2)
H27 0.4769 −0.3107 0.2901 0.091*
C28 0.5149 (3) −0.3436 (11) 0.3434 (2) 0.084 (2)
H28 0.5397 −0.4657 0.3375 0.101*
C29 0.5173 (3) −0.2589 (13) 0.3819 (2) 0.092 (2)
H29 0.5430 −0.3244 0.4014 0.111*
C30 0.4813 (3) −0.0799 (11) 0.3897 (2) 0.078 (2)
H30 0.4836 −0.0205 0.4148 0.094*
C31 0.4410 (3) 0.0179 (10) 0.36158 (19) 0.0547 (16)
C32 0.4021 (3) 0.1999 (9) 0.36920 (17) 0.0573 (16)
H32 0.4032 0.2579 0.3944 0.069*
C33 0.4184 (3) 1.8592 (9) 0.5359 (2) 0.080 (2)
H33 0.4346 1.9553 0.5545 0.096*
C34 0.4305 (3) 1.8749 (10) 0.4964 (2) 0.0744 (19)
H34 0.4572 1.9798 0.4848 0.089*
C35 0.3980 (2) 1.7149 (9) 0.47596 (17) 0.0592 (16)
H35 0.3994 1.7044 0.4486 0.071*
C36 0.3635 (2) 1.5730 (8) 0.49900 (16) 0.0495 (14)
C37 0.3271 (3) 1.3905 (8) 0.48448 (16) 0.0524 (15)
H37 0.3261 1.3596 0.4577 0.063*
C38 0.2277 (3) 0.9641 (9) 0.51485 (17) 0.0455 (15)
C39 0.1955 (2) 0.7777 (8) 0.49573 (14) 0.0381 (13)
C40 0.2039 (2) 0.7167 (8) 0.45615 (16) 0.0461 (14)
C41 0.1721 (3) 0.5405 (9) 0.44212 (16) 0.0573 (16)
H41 0.1794 0.5006 0.4161 0.069*
C42 0.1280 (3) 0.4142 (8) 0.46550 (17) 0.0492 (15)
C43 0.0939 (3) 0.2328 (9) 0.45136 (18) 0.0686 (18)
H43 0.0990 0.1920 0.4252 0.082*
C44 0.0541 (3) 0.1183 (9) 0.47519 (19) 0.0651 (17)
H44 0.0310 0.0003 0.4654 0.078*
C45 0.0470 (2) 0.1750 (9) 0.51481 (19) 0.0633 (17)
H45 0.0196 0.0923 0.5311 0.076*
C46 0.0790 (3) 0.3478 (8) 0.53006 (16) 0.0531 (15)
H46 0.0735 0.3849 0.5564 0.064*
C47 0.1208 (2) 0.4700 (8) 0.50523 (16) 0.0447 (14)
C48 0.1555 (2) 0.6543 (8) 0.51967 (15) 0.0448 (14)
H48 0.1508 0.6918 0.5460 0.054*
N3 0.2524 (2) 0.7774 (8) 0.33437 (14) 0.0580 (14)
N4 0.2909 (2) 0.5966 (7) 0.32609 (14) 0.0588 (13)
H53 0.2943 0.5528 0.3022 0.071*
N5 0.2959 (2) 1.2714 (7) 0.50920 (13) 0.0537 (12)
N6 0.2642 (2) 1.0966 (7) 0.49271 (13) 0.0504 (12)
H54 0.2680 1.0729 0.4679 0.061*
O2 0.31792 (19) 0.5390 (6) 0.38926 (11) 0.0695 (12)
O3 0.21923 (17) 1.0000 (5) 0.55059 (11) 0.0628 (10)
O5 0.32458 (17) 0.3078 (5) 0.27397 (10) 0.0675 (11)
H50 0.3139 0.2188 0.2574 0.101*
O6 0.2452 (2) 0.8363 (6) 0.43242 (11) 0.0657 (11)
H51 0.2565 0.7649 0.4133 0.099*
S2 0.17219 (9) 1.1672 (3) 0.35224 (5) 0.0873 (5)
S3 0.36965 (8) 1.6406 (3) 0.54683 (5) 0.0731 (5)
C1 0.1105 (3) 0.8520 (9) 0.1823 (2) 0.078 (2)
H1 0.0887 0.9485 0.1988 0.094*
C2 0.1095 (3) 0.8610 (10) 0.1431 (2) 0.077 (2)
H2 0.0854 0.9638 0.1291 0.093*
C3 0.1482 (2) 0.7003 (8) 0.12479 (16) 0.0556 (16)
H3 0.1535 0.6864 0.0977 0.067*
C4 0.1772 (2) 0.5665 (8) 0.15220 (17) 0.0543 (15)
C5 0.2184 (2) 0.3795 (8) 0.14311 (17) 0.0520 (15)
H5 0.2278 0.3432 0.1171 0.062*
C6 0.3083 (3) −0.0401 (8) 0.18524 (19) 0.0481 (15)
C7 0.3449 (2) −0.2287 (8) 0.16877 (15) 0.0398 (13)
C8 0.3466 (2) −0.2926 (8) 0.12870 (17) 0.0507 (16)
C9 0.3838 (3) −0.4635 (8) 0.11708 (17) 0.0536 (15)
H9 0.3842 −0.5012 0.0906 0.064*
C10 0.4212 (3) −0.5836 (8) 0.14371 (19) 0.0493 (15)
C11 0.4587 (3) −0.7676 (10) 0.13163 (19) 0.0676 (18)
H11 0.4596 −0.8079 0.1053 0.081*
C12 0.4926 (3) −0.8815 (9) 0.1585 (2) 0.0762 (19)
H12 0.5179 −0.9994 0.1506 0.091*
C13 0.4904 (3) −0.8241 (10) 0.1989 (2) 0.0767 (19)
H13 0.5135 −0.9056 0.2174 0.092*
C14 0.4548 (3) −0.6509 (9) 0.21041 (18) 0.0634 (18)
H14 0.4543 −0.6134 0.2369 0.076*
C15 0.4193 (2) −0.5292 (8) 0.18397 (18) 0.0463 (15)
C16 0.3803 (2) −0.3475 (8) 0.19406 (16) 0.0495 (14)
H16 0.3792 −0.3078 0.2205 0.059*
N2 0.27772 (19) 0.0878 (6) 0.15848 (14) 0.0506 (12)
H2A 0.2806 0.0598 0.1337 0.061*
O1 0.30712 (18) −0.0019 (6) 0.22020 (12) 0.0651 (11)
S1 0.15723 (9) 0.6402 (2) 0.19813 (5) 0.0774 (5)
N1 0.2415 (2) 0.2660 (7) 0.17149 (14) 0.0509 (12)
O4 0.31007 (17) −0.1791 (5) 0.10045 (10) 0.0603 (10)
H4 0.2714 −0.2252 0.0995 0.090*

[TableWrap ID: d1e1817]
U11 U22 U33 U12 U13 U23
C17 0.069 (4) 0.070 (4) 0.093 (3) 0.007 (3) 0.021 (4) −0.023 (3)
C18 0.099 (5) 0.064 (4) 0.093 (3) 0.024 (3) 0.009 (4) −0.010 (3)
C19 0.066 (4) 0.054 (4) 0.070 (2) 0.017 (3) 0.009 (3) −0.004 (3)
C20 0.059 (4) 0.060 (4) 0.072 (3) 0.009 (2) 0.007 (3) −0.009 (3)
C21 0.069 (4) 0.067 (5) 0.058 (5) −0.002 (3) 0.001 (4) −0.006 (4)
C22 0.047 (4) 0.059 (4) 0.043 (4) −0.010 (3) 0.003 (3) −0.001 (4)
C23 0.046 (4) 0.056 (4) 0.038 (4) −0.005 (3) 0.007 (3) −0.007 (3)
C24 0.050 (4) 0.051 (4) 0.059 (4) 0.001 (3) 0.004 (3) −0.002 (3)
C25 0.065 (4) 0.056 (4) 0.063 (4) 0.013 (3) −0.007 (3) −0.018 (3)
C26 0.044 (4) 0.047 (4) 0.067 (5) 0.001 (3) 0.005 (3) 0.005 (3)
C27 0.070 (5) 0.061 (4) 0.097 (6) 0.002 (3) −0.012 (4) 0.007 (4)
C28 0.065 (5) 0.069 (5) 0.118 (7) 0.008 (4) 0.013 (5) 0.022 (5)
C29 0.073 (5) 0.107 (7) 0.097 (7) 0.001 (5) −0.002 (5) 0.058 (6)
C30 0.066 (5) 0.090 (6) 0.077 (5) −0.004 (4) 0.011 (4) 0.023 (4)
C31 0.047 (4) 0.064 (4) 0.053 (5) −0.004 (3) 0.000 (3) 0.010 (4)
C32 0.056 (4) 0.066 (4) 0.051 (4) −0.014 (3) −0.003 (3) 0.002 (3)
C33 0.056 (4) 0.067 (4) 0.118 (7) −0.016 (3) −0.017 (4) −0.015 (5)
C34 0.070 (5) 0.071 (5) 0.082 (5) −0.011 (4) −0.009 (4) 0.011 (4)
C35 0.059 (4) 0.063 (4) 0.057 (4) −0.004 (3) 0.000 (3) −0.002 (4)
C36 0.044 (3) 0.048 (4) 0.056 (4) 0.007 (3) −0.002 (3) 0.006 (3)
C37 0.059 (4) 0.054 (4) 0.045 (4) −0.001 (3) 0.005 (3) −0.006 (3)
C38 0.043 (4) 0.053 (4) 0.041 (4) 0.009 (3) −0.002 (3) −0.006 (3)
C39 0.043 (3) 0.044 (3) 0.028 (3) 0.004 (2) 0.002 (3) −0.010 (3)
C40 0.043 (4) 0.043 (4) 0.052 (4) 0.005 (3) 0.007 (3) 0.004 (3)
C41 0.061 (4) 0.067 (4) 0.044 (4) −0.009 (3) 0.006 (3) −0.021 (3)
C42 0.044 (4) 0.049 (4) 0.055 (4) 0.004 (3) −0.006 (3) −0.006 (3)
C43 0.065 (5) 0.075 (5) 0.065 (5) −0.025 (3) 0.003 (4) −0.009 (4)
C44 0.061 (4) 0.066 (5) 0.069 (5) −0.008 (3) −0.006 (4) −0.009 (4)
C45 0.051 (4) 0.065 (5) 0.073 (5) −0.009 (3) 0.008 (3) 0.009 (4)
C46 0.063 (4) 0.053 (4) 0.043 (4) 0.001 (3) 0.001 (3) 0.003 (3)
C47 0.041 (3) 0.042 (3) 0.051 (4) 0.009 (3) −0.004 (3) 0.002 (3)
C48 0.057 (4) 0.041 (3) 0.037 (3) 0.018 (3) 0.000 (3) −0.005 (3)
N3 0.058 (4) 0.050 (3) 0.066 (4) −0.005 (3) 0.012 (3) −0.019 (3)
N4 0.073 (4) 0.061 (4) 0.042 (3) 0.002 (3) 0.008 (3) −0.018 (3)
N5 0.058 (3) 0.045 (3) 0.058 (4) 0.003 (2) −0.004 (3) −0.008 (3)
N6 0.064 (3) 0.047 (3) 0.040 (3) −0.004 (2) 0.005 (3) −0.012 (2)
O2 0.090 (3) 0.081 (3) 0.037 (3) 0.003 (2) 0.006 (2) −0.014 (2)
O3 0.074 (3) 0.068 (3) 0.047 (3) −0.0139 (19) 0.009 (2) −0.011 (2)
O5 0.086 (3) 0.064 (3) 0.053 (3) 0.020 (2) −0.007 (2) −0.018 (2)
O6 0.079 (3) 0.072 (3) 0.045 (3) −0.016 (2) 0.012 (2) −0.017 (2)
S2 0.0958 (14) 0.0883 (13) 0.0779 (13) 0.0070 (10) 0.0068 (11) −0.0152 (11)
S3 0.0846 (13) 0.0801 (12) 0.0545 (11) −0.0074 (9) −0.0003 (10) −0.0064 (10)
C1 0.071 (5) 0.061 (5) 0.103 (7) 0.009 (3) 0.015 (4) −0.018 (5)
C2 0.058 (4) 0.057 (5) 0.116 (7) 0.006 (3) −0.003 (4) −0.002 (5)
C3 0.062 (4) 0.055 (4) 0.050 (4) −0.001 (3) 0.009 (3) 0.008 (3)
C4 0.053 (4) 0.040 (4) 0.069 (5) 0.000 (3) 0.008 (3) −0.006 (3)
C5 0.059 (4) 0.044 (4) 0.052 (4) −0.001 (3) −0.002 (3) −0.002 (3)
C6 0.047 (4) 0.043 (4) 0.055 (4) −0.006 (3) −0.001 (3) −0.002 (3)
C7 0.046 (3) 0.041 (3) 0.032 (4) 0.000 (3) −0.005 (3) −0.003 (3)
C8 0.044 (4) 0.052 (4) 0.056 (4) 0.008 (3) −0.006 (3) 0.004 (3)
C9 0.065 (4) 0.046 (4) 0.050 (4) 0.011 (3) 0.004 (3) −0.016 (3)
C10 0.040 (4) 0.044 (4) 0.063 (5) 0.001 (3) 0.004 (3) −0.002 (3)
C11 0.061 (4) 0.069 (5) 0.073 (5) −0.006 (4) 0.001 (4) −0.003 (4)
C12 0.060 (5) 0.070 (5) 0.098 (6) 0.012 (3) −0.003 (5) −0.012 (5)
C13 0.062 (5) 0.066 (5) 0.102 (6) 0.003 (3) −0.010 (4) 0.014 (4)
C14 0.057 (4) 0.053 (4) 0.080 (5) 0.014 (3) 0.003 (3) −0.009 (4)
C15 0.038 (4) 0.043 (4) 0.058 (5) 0.003 (3) −0.002 (3) 0.003 (3)
C16 0.047 (3) 0.057 (4) 0.045 (4) −0.007 (3) −0.005 (3) −0.008 (3)
N2 0.061 (3) 0.049 (3) 0.042 (3) 0.002 (2) −0.005 (3) −0.009 (3)
O1 0.084 (3) 0.065 (3) 0.047 (3) 0.014 (2) −0.002 (2) −0.011 (2)
S1 0.0790 (12) 0.0771 (12) 0.0762 (12) 0.0032 (10) 0.0082 (10) −0.0121 (11)
N1 0.057 (3) 0.039 (3) 0.057 (3) 0.007 (2) 0.004 (3) −0.003 (2)
O4 0.065 (3) 0.069 (3) 0.048 (3) 0.010 (2) 0.006 (2) −0.012 (2)

[TableWrap ID: d1e3001]
C17—C18 1.306 (8) C42—C47 1.400 (7)
C17—S2 1.695 (6) C43—C44 1.337 (7)
C17—H17 0.9300 C43—H43 0.9300
C18—C19 1.398 (6) C44—C45 1.398 (7)
C18—H18 0.9300 C44—H44 0.9300
C19—C20 1.409 (7) C45—C46 1.355 (6)
C19—H19 0.9300 C45—H45 0.9300
C20—C21 1.442 (7) C46—C47 1.407 (6)
C20—S2 1.694 (6) C46—H46 0.9300
C21—N3 1.274 (6) C47—C48 1.427 (6)
C21—H21 0.9300 C48—H48 0.9300
C22—O2 1.225 (6) N3—N4 1.392 (5)
C22—N4 1.323 (6) N4—H53 0.8600
C22—C23 1.510 (7) N5—N6 1.379 (5)
C23—C32 1.369 (6) N6—H54 0.8600
C23—C24 1.408 (7) O5—O1 2.682 (5)
C24—O5 1.382 (6) O5—H50 0.8199
C24—C25 1.370 (6) O6—H51 0.8200
C25—C26 1.387 (7) C1—C2 1.332 (7)
C25—H25 0.9300 C1—S1 1.702 (6)
C26—C31 1.393 (7) C1—H1 0.9300
C26—C27 1.415 (7) C2—C3 1.409 (7)
C27—C28 1.336 (8) C2—H2 0.9300
C27—H27 0.9300 C3—C4 1.376 (6)
C28—C29 1.409 (9) C3—H3 0.9300
C28—H28 0.9300 C4—C5 1.459 (7)
C29—C30 1.353 (8) C4—S1 1.673 (6)
C29—H29 0.9300 C5—N1 1.281 (6)
C30—C31 1.387 (7) C5—H5 0.9300
C30—H30 0.9300 C6—O1 1.211 (6)
C31—C32 1.398 (6) C6—N2 1.353 (6)
C32—H32 0.9300 C6—C7 1.493 (7)
C33—C34 1.365 (8) C7—C16 1.334 (6)
C33—S3 1.713 (6) C7—C8 1.418 (7)
C33—H33 0.9300 C8—C9 1.356 (6)
C34—C35 1.376 (7) C8—O4 1.396 (5)
C34—H34 0.9300 C9—C10 1.389 (7)
C35—C36 1.365 (6) C9—H9 0.9300
C35—H35 0.9300 C10—C15 1.409 (7)
C36—C37 1.437 (6) C10—C11 1.430 (7)
C36—S3 1.682 (5) C11—C12 1.338 (7)
C37—N5 1.280 (6) C11—H11 0.9300
C37—H37 0.9300 C12—C13 1.418 (8)
C38—O3 1.245 (6) C12—H12 0.9300
C38—N6 1.332 (6) C13—C14 1.350 (7)
C38—C39 1.478 (6) C13—H13 0.9300
C39—C48 1.373 (6) C14—C15 1.370 (7)
C39—C40 1.406 (6) C14—H14 0.9300
C40—C41 1.356 (6) C15—C16 1.415 (6)
C40—O6 1.370 (5) C16—H16 0.9300
C41—C42 1.420 (7) N2—N1 1.397 (5)
C41—H41 0.9300 N2—H2A 0.8600
C42—C43 1.404 (7) O4—H4 0.8200
C18—C17—S2 111.8 (5) C45—C44—H44 119.8
C18—C17—H17 124.1 C46—C45—C44 121.5 (6)
S2—C17—H17 124.1 C46—C45—H45 119.3
C17—C18—C19 116.8 (6) C44—C45—H45 119.3
C17—C18—H18 121.6 C45—C46—C47 118.7 (5)
C19—C18—H18 121.6 C45—C46—H46 120.7
C18—C19—C20 107.5 (6) C47—C46—H46 120.7
C18—C19—H19 126.2 C42—C47—C46 120.1 (5)
C20—C19—H19 126.2 C42—C47—C48 118.9 (5)
C19—C20—C21 128.1 (6) C46—C47—C48 121.0 (5)
C19—C20—S2 112.6 (4) C39—C48—C47 121.8 (5)
C21—C20—S2 119.3 (5) C39—C48—H48 119.1
N3—C21—C20 121.8 (6) C47—C48—H48 119.1
N3—C21—H21 119.1 C21—N3—N4 114.5 (5)
C20—C21—H21 119.1 C22—N4—N3 121.2 (5)
O2—C22—N4 122.9 (5) C22—N4—H53 119.4
O2—C22—C23 121.1 (5) N3—N4—H53 119.4
N4—C22—C23 115.9 (5) C37—N5—N6 114.5 (5)
C32—C23—C24 117.7 (5) C38—N6—N5 120.7 (4)
C32—C23—C22 117.2 (5) C38—N6—H54 119.6
C24—C23—C22 125.1 (5) N5—N6—H54 119.6
O5—C24—C25 120.6 (5) C24—O5—O1 103.9 (3)
O5—C24—C23 119.6 (5) C24—O5—H50 109.6
C25—C24—C23 119.8 (6) O1—O5—H50 7.9
C24—C25—C26 121.9 (6) C40—O6—H51 109.5
C24—C25—H25 119.0 C17—S2—C20 91.1 (3)
C26—C25—H25 119.0 C36—S3—C33 91.8 (3)
C25—C26—C31 119.4 (5) C2—C1—S1 110.9 (5)
C25—C26—C27 121.8 (6) C2—C1—H1 124.6
C31—C26—C27 118.9 (6) S1—C1—H1 124.6
C28—C27—C26 120.3 (7) C1—C2—C3 113.7 (7)
C28—C27—H27 119.9 C1—C2—H2 123.1
C26—C27—H27 119.9 C3—C2—H2 123.1
C27—C28—C29 121.4 (7) C4—C3—C2 111.2 (6)
C27—C28—H28 119.3 C4—C3—H3 124.4
C29—C28—H28 119.3 C2—C3—H3 124.4
C30—C29—C28 118.3 (7) C3—C4—C5 125.3 (5)
C30—C29—H29 120.8 C3—C4—S1 111.4 (4)
C28—C29—H29 120.8 C5—C4—S1 123.3 (5)
C29—C30—C31 122.2 (7) N1—C5—C4 119.0 (5)
C29—C30—H30 118.9 N1—C5—H5 120.5
C31—C30—H30 118.9 C4—C5—H5 120.5
C30—C31—C26 118.9 (6) O1—C6—N2 122.2 (5)
C30—C31—C32 123.3 (6) O1—C6—C7 122.1 (5)
C26—C31—C32 117.8 (6) N2—C6—C7 115.6 (5)
C23—C32—C31 123.4 (6) C16—C7—C8 116.6 (5)
C23—C32—H32 118.3 C16—C7—C6 117.0 (5)
C31—C32—H32 118.3 C8—C7—C6 126.4 (5)
C34—C33—S3 111.7 (5) C9—C8—O4 118.8 (5)
C34—C33—H33 124.2 C9—C8—C7 120.9 (5)
S3—C33—H33 124.2 O4—C8—C7 120.2 (5)
C33—C34—C35 111.1 (6) C8—C9—C10 121.7 (5)
C33—C34—H34 124.4 C8—C9—H9 119.1
C35—C34—H34 124.4 C10—C9—H9 119.1
C36—C35—C34 114.6 (6) C9—C10—C15 119.1 (5)
C36—C35—H35 122.7 C9—C10—C11 121.7 (6)
C34—C35—H35 122.7 C15—C10—C11 119.1 (5)
C35—C36—C37 124.8 (5) C12—C11—C10 119.6 (6)
C35—C36—S3 110.7 (4) C12—C11—H11 120.2
C37—C36—S3 124.5 (4) C10—C11—H11 120.2
N5—C37—C36 118.6 (5) C11—C12—C13 120.6 (6)
N5—C37—H37 120.7 C11—C12—H12 119.7
C36—C37—H37 120.7 C13—C12—H12 119.7
O3—C38—N6 120.7 (5) C14—C13—C12 120.0 (6)
O3—C38—C39 120.8 (5) C14—C13—H13 120.0
N6—C38—C39 118.5 (5) C12—C13—H13 120.0
C48—C39—C40 118.8 (5) C13—C14—C15 121.6 (6)
C48—C39—C38 115.6 (5) C13—C14—H14 119.2
C40—C39—C38 125.6 (5) C15—C14—H14 119.2
C41—C40—O6 121.0 (5) C14—C15—C10 119.2 (5)
C41—C40—C39 120.0 (5) C14—C15—C16 124.5 (6)
O6—C40—C39 119.0 (5) C10—C15—C16 116.3 (5)
C40—C41—C42 122.8 (5) C7—C16—C15 125.3 (5)
C40—C41—H41 118.6 C7—C16—H16 117.4
C42—C41—H41 118.6 C15—C16—H16 117.4
C43—C42—C47 118.8 (5) C6—N2—N1 119.3 (5)
C43—C42—C41 123.6 (5) C6—N2—H2A 120.4
C47—C42—C41 117.5 (5) N1—N2—H2A 120.4
C44—C43—C42 120.6 (6) C6—O1—O5 143.8 (4)
C44—C43—H43 119.7 C4—S1—C1 92.8 (3)
C42—C43—H43 119.7 C5—N1—N2 112.8 (5)
C43—C44—C45 120.4 (6) C8—O4—H4 109.5
C43—C44—H44 119.8
S2—C17—C18—C19 2.5 (8) C38—C39—C48—C47 179.6 (4)
C17—C18—C19—C20 −3.3 (8) C42—C47—C48—C39 −0.1 (7)
C18—C19—C20—C21 −176.7 (6) C46—C47—C48—C39 −178.8 (5)
C18—C19—C20—S2 2.7 (6) C20—C21—N3—N4 178.5 (5)
C19—C20—C21—N3 −176.1 (6) O2—C22—N4—N3 2.8 (8)
S2—C20—C21—N3 4.5 (8) C23—C22—N4—N3 179.8 (4)
O2—C22—C23—C32 −10.7 (8) C21—N3—N4—C22 175.6 (5)
N4—C22—C23—C32 172.2 (5) C36—C37—N5—N6 −178.1 (4)
O2—C22—C23—C24 170.0 (5) O3—C38—N6—N5 3.0 (7)
N4—C22—C23—C24 −7.1 (8) C39—C38—N6—N5 −179.2 (4)
C32—C23—C24—O5 −177.9 (5) C37—N5—N6—C38 −177.3 (5)
C22—C23—C24—O5 1.4 (8) C25—C24—O5—O1 21.7 (6)
C32—C23—C24—C25 1.7 (8) C23—C24—O5—O1 −158.7 (4)
C22—C23—C24—C25 −179.0 (5) C18—C17—S2—C20 −0.6 (6)
O5—C24—C25—C26 178.6 (5) C19—C20—S2—C17 −1.3 (5)
C23—C24—C25—C26 −1.0 (8) C21—C20—S2—C17 178.1 (5)
C24—C25—C26—C31 0.0 (8) C35—C36—S3—C33 0.0 (4)
C24—C25—C26—C27 179.5 (5) C37—C36—S3—C33 179.9 (4)
C25—C26—C27—C28 −179.7 (6) C34—C33—S3—C36 −1.4 (5)
C31—C26—C27—C28 −0.2 (9) S1—C1—C2—C3 −1.8 (8)
C26—C27—C28—C29 −0.2 (10) C1—C2—C3—C4 1.5 (8)
C27—C28—C29—C30 −0.6 (10) C2—C3—C4—C5 177.8 (5)
C28—C29—C30—C31 1.9 (10) C2—C3—C4—S1 −0.4 (6)
C29—C30—C31—C26 −2.2 (9) C3—C4—C5—N1 −178.9 (5)
C29—C30—C31—C32 178.4 (6) S1—C4—C5—N1 −0.9 (7)
C25—C26—C31—C30 −179.1 (5) O1—C6—C7—C16 −4.1 (8)
C27—C26—C31—C30 1.4 (8) N2—C6—C7—C16 174.5 (5)
C25—C26—C31—C32 0.2 (8) O1—C6—C7—C8 176.8 (5)
C27—C26—C31—C32 −179.3 (5) N2—C6—C7—C8 −4.7 (7)
C24—C23—C32—C31 −1.5 (8) C16—C7—C8—C9 −1.4 (7)
C22—C23—C32—C31 179.2 (5) C6—C7—C8—C9 177.7 (5)
C30—C31—C32—C23 179.9 (5) C16—C7—C8—O4 179.0 (4)
C26—C31—C32—C23 0.5 (8) C6—C7—C8—O4 −1.9 (8)
S3—C33—C34—C35 2.3 (7) O4—C8—C9—C10 −179.9 (5)
C33—C34—C35—C36 −2.4 (8) C7—C8—C9—C10 0.5 (8)
C34—C35—C36—C37 −178.6 (5) C8—C9—C10—C15 1.3 (8)
C34—C35—C36—S3 1.4 (6) C8—C9—C10—C11 178.1 (5)
C35—C36—C37—N5 −178.9 (5) C9—C10—C11—C12 −178.3 (5)
S3—C36—C37—N5 1.1 (7) C15—C10—C11—C12 −1.6 (8)
O3—C38—C39—C48 1.5 (7) C10—C11—C12—C13 1.4 (9)
N6—C38—C39—C48 −176.4 (5) C11—C12—C13—C14 −1.2 (9)
O3—C38—C39—C40 −177.1 (5) C12—C13—C14—C15 1.0 (9)
N6—C38—C39—C40 5.0 (7) C13—C14—C15—C10 −1.2 (8)
C48—C39—C40—C41 0.8 (8) C13—C14—C15—C16 179.2 (5)
C38—C39—C40—C41 179.3 (5) C9—C10—C15—C14 178.3 (5)
C48—C39—C40—O6 −178.4 (4) C11—C10—C15—C14 1.5 (8)
C38—C39—C40—O6 0.2 (7) C9—C10—C15—C16 −2.1 (7)
O6—C40—C41—C42 −178.9 (5) C11—C10—C15—C16 −178.9 (4)
C39—C40—C41—C42 2.0 (8) C8—C7—C16—C15 0.6 (7)
C40—C41—C42—C43 179.1 (5) C6—C7—C16—C15 −178.6 (5)
C40—C41—C42—C47 −3.7 (8) C14—C15—C16—C7 −179.2 (5)
C47—C42—C43—C44 1.5 (9) C10—C15—C16—C7 1.2 (8)
C41—C42—C43—C44 178.7 (6) O1—C6—N2—N1 −2.4 (8)
C42—C43—C44—C45 −1.4 (9) C7—C6—N2—N1 179.1 (4)
C43—C44—C45—C46 1.0 (9) N2—C6—O1—O5 −46.8 (9)
C44—C45—C46—C47 −0.8 (8) C7—C6—O1—O5 131.6 (5)
C43—C42—C47—C46 −1.3 (7) C24—O5—O1—C6 −136.0 (7)
C41—C42—C47—C46 −178.6 (5) C3—C4—S1—C1 −0.5 (4)
C43—C42—C47—C48 180.0 (5) C5—C4—S1—C1 −178.8 (5)
C41—C42—C47—C48 2.7 (7) C2—C1—S1—C4 1.3 (5)
C45—C46—C47—C42 0.9 (7) C4—C5—N1—N2 177.6 (4)
C45—C46—C47—C48 179.6 (5) C6—N2—N1—C5 176.4 (5)
C40—C39—C48—C47 −1.7 (7)

[TableWrap ID: d1e4953]
D—H···A D—H H···A D···A D—H···A
O6—H51···O2 0.82 2.03 2.771 (5) 149
N6—H54···O6 0.86 1.96 2.641 (5) 135
N2—H2A···O4 0.86 1.96 2.660 (5) 138
N4—H53···O5 0.86 1.90 2.614 (5) 139
O5—H50···O1 0.82 1.87 2.682 (5) 169
O4—H4···O3i 0.82 2.40 2.688 (5) 102


Article Categories:
  • Organic Papers


Previous Document:  3-(4-Fluoro-benzyl-idene)-1,5-dioxa-spiro-[5.5]undecane-2,4-dione.
Next Document:  A monoclinic modification of propane-1,3-diyl bis-(pyridine-3-carboxyl-ate).