Literature DB >> 21201915

1,3-Di-3-pyridyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine.

Betül Sen, Zuhal Turgut, Emel Pelit, Muhittin Aygün.   

Abstract

In the crystal structure of the title compound, C(22)H(17)N(3)O, the oxazine ring has a half-chair conformation. The dihedral angles between the best least-squares plane through the pyridine rings and the planar part (O-C-C-C-N) of the oxazine ring are 72.14 (6) and 35.44 (7)°, the smaller angle involving the pyridine ring adjacent to the oxazine O atom. The mol-ecule has two stereogenic centers at the oxazine carbons, RS and SR. The crystal packing reveals that symmetry-related mol-ecules are linked by inter-molecular N-H⋯N hydrogen bonds to form chains parallel to the b axis.

Entities:  

Year:  2008        PMID： 21201915      PMCID： PMC2960797          DOI： 10.1107/S1600536808003887

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


Related literature

For related literature, see: Kurz et al. (2005 ▶); Turgut et al. (2007 ▶); Szatmari et al. (2003 ▶, 2004 ▶); Bernstein et al. (1995 ▶); Cremer & Pople (1975 ▶).

Experimental

Crystal data

C22H17N3O M = 339.39 Monoclinic, a = 12.1720 (8) Å b = 8.0444 (6) Å c = 18.7716 (15) Å β = 112.615 (5)° V = 1696.7 (2) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 293 (2) K 0.28 × 0.22 × 0.12 mm

Data collection

Stoe IPDSII diffractometer Absorption correction: none 15207 measured reflections 3703 independent reflections 1786 reflections with I > 2σ(I) R int = 0.124

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.092 S = 0.80 3703 reflections 304 parameters All H-atom parameters refined Δρmax = 0.12 e Å−3 Δρmin = −0.13 e Å−3 Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003887/su2043sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003887/su2043Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H17N3OF000 = 712
Mr = 339.39Dx = 1.329 Mg m−3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10289 reflections
a = 12.1720 (8) Åθ = 1.7–27.2º
b = 8.0444 (6) ŵ = 0.08 mm−1
c = 18.7716 (15) ÅT = 293 (2) K
β = 112.615 (5)ºPrism, pale yellow
V = 1696.7 (2) Å30.28 × 0.22 × 0.12 mm
Z = 4
Stoe IPDSII diffractometer3703 independent reflections
Radiation source: fine-focus sealed tube1786 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.124
Detector resolution: 6.67 pixels mm-1θmax = 27.2º
T = 293(2) Kθmin = 2.4º
ω and φ scansh = −15→15
Absorption correction: nonek = −10→10
15207 measured reflectionsl = −24→24
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.041  w = 1/[σ2(Fo2) + (0.0317P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max < 0.001
S = 0.80Δρmax = 0.12 e Å−3
3703 reflectionsΔρmin = −0.13 e Å−3
304 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0155 (15)
Secondary atom site location: difference Fourier map
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
O10.50525 (11)0.70176 (16)0.05782 (6)0.0613 (3)
N10.34476 (13)0.63357 (19)0.09666 (7)0.0530 (4)
N20.07931 (16)0.2535 (2)0.01583 (9)0.0797 (5)
N30.61988 (16)0.4333 (2)0.30101 (8)0.0708 (5)
C10.20165 (16)0.4668 (2)−0.00607 (8)0.0515 (4)
C20.22195 (18)0.3658 (2)−0.05879 (10)0.0624 (5)
C30.1718 (2)0.2087 (3)−0.07310 (11)0.0721 (6)
C40.1012 (2)0.1592 (3)−0.03549 (11)0.0750 (6)
C50.13038 (19)0.4030 (3)0.02947 (10)0.0664 (5)
C60.55109 (16)0.5779 (2)0.17981 (8)0.0518 (4)
C70.54203 (19)0.4545 (2)0.22813 (10)0.0619 (5)
C80.7097 (2)0.5402 (3)0.32714 (11)0.0717 (6)
C90.7258 (2)0.6678 (3)0.28396 (10)0.0713 (6)
C100.64504 (18)0.6866 (2)0.20842 (9)0.0621 (5)
C110.42404 (16)0.7472 (2)−0.01352 (8)0.0521 (4)
C120.4760 (2)0.8298 (2)−0.05937 (10)0.0581 (5)
C130.40609 (19)0.8731 (2)−0.13285 (10)0.0614 (5)
C140.28339 (18)0.8404 (2)−0.16314 (9)0.0571 (5)
C150.2110 (2)0.8834 (3)−0.24001 (10)0.0703 (6)
C160.0929 (2)0.8602 (3)−0.26809 (12)0.0854 (7)
C170.0389 (2)0.7933 (3)−0.22063 (12)0.0884 (7)
C180.10616 (19)0.7473 (3)−0.14611 (10)0.0703 (6)
C190.23078 (17)0.7670 (2)−0.11493 (9)0.0548 (5)
C200.30495 (16)0.7173 (2)−0.03826 (8)0.0506 (4)
C210.25461 (17)0.6395 (2)0.01656 (8)0.0530 (4)
C220.45819 (16)0.5869 (2)0.09848 (8)0.0526 (4)
H10.3522 (17)0.738 (3)0.1247 (10)0.080 (6)*
H20.2726 (17)0.408 (2)−0.0873 (9)0.073 (5)*
H30.1834 (19)0.141 (3)−0.1108 (12)0.099 (7)*
H40.0621 (19)0.051 (3)−0.0461 (11)0.089 (7)*
H50.1146 (18)0.475 (3)0.0680 (10)0.083 (6)*
H70.4767 (18)0.367 (3)0.2099 (10)0.077 (6)*
H80.7714 (19)0.522 (3)0.3822 (11)0.094 (7)*
H90.7932 (19)0.744 (3)0.3052 (10)0.083 (6)*
H100.6560 (18)0.777 (3)0.1759 (10)0.090 (6)*
H120.5600 (18)0.853 (2)−0.0360 (9)0.064 (5)*
H130.4472 (17)0.928 (2)−0.1648 (9)0.076 (5)*
H150.2541 (18)0.935 (3)−0.2732 (10)0.087 (6)*
H160.041 (2)0.891 (3)−0.3203 (13)0.113 (8)*
H17−0.047 (2)0.776 (3)−0.2404 (12)0.107 (8)*
H180.0647 (16)0.705 (2)−0.1138 (9)0.066 (5)*
H210.1904 (15)0.710 (2)0.0184 (8)0.055 (5)*
H220.4510 (15)0.472 (2)0.0725 (8)0.057 (5)*
U11U22U33U12U13U23
O10.0548 (8)0.0777 (9)0.0510 (6)−0.0024 (6)0.0199 (6)0.0111 (6)
N10.0553 (10)0.0593 (10)0.0451 (7)−0.0015 (7)0.0201 (7)−0.0059 (6)
N20.0853 (14)0.0791 (13)0.0802 (10)−0.0210 (10)0.0380 (10)−0.0002 (9)
N30.0791 (13)0.0742 (12)0.0544 (9)−0.0034 (10)0.0205 (8)0.0110 (7)
C10.0464 (11)0.0572 (11)0.0479 (8)−0.0006 (8)0.0147 (8)0.0004 (7)
C20.0677 (14)0.0614 (12)0.0625 (10)−0.0053 (10)0.0296 (10)−0.0082 (9)
C30.0791 (16)0.0637 (13)0.0711 (12)−0.0062 (11)0.0261 (11)−0.0124 (10)
C40.0768 (16)0.0669 (14)0.0712 (12)−0.0135 (12)0.0172 (11)0.0009 (11)
C50.0717 (15)0.0705 (13)0.0615 (10)−0.0078 (11)0.0305 (10)−0.0007 (10)
C60.0556 (12)0.0525 (10)0.0492 (9)0.0008 (9)0.0223 (8)−0.0024 (7)
C70.0701 (15)0.0624 (12)0.0539 (10)−0.0053 (10)0.0246 (10)0.0031 (9)
C80.0690 (16)0.0815 (15)0.0561 (11)−0.0004 (12)0.0146 (10)0.0068 (10)
C90.0666 (15)0.0794 (15)0.0596 (11)−0.0132 (12)0.0152 (10)0.0003 (10)
C100.0683 (14)0.0639 (12)0.0529 (10)−0.0049 (10)0.0217 (9)0.0019 (9)
C110.0582 (13)0.0539 (10)0.0433 (8)0.0026 (9)0.0183 (8)0.0005 (7)
C120.0592 (14)0.0595 (11)0.0568 (10)−0.0026 (10)0.0236 (9)0.0017 (8)
C130.0733 (15)0.0580 (11)0.0573 (10)−0.0009 (10)0.0301 (10)0.0073 (8)
C140.0625 (14)0.0563 (11)0.0516 (9)0.0025 (9)0.0209 (9)0.0041 (8)
C150.0777 (18)0.0720 (13)0.0576 (11)0.0021 (11)0.0219 (11)0.0106 (9)
C160.0798 (19)0.1046 (18)0.0596 (12)−0.0013 (14)0.0131 (12)0.0173 (12)
C170.0630 (18)0.119 (2)0.0697 (13)0.0006 (14)0.0104 (11)0.0228 (12)
C180.0620 (15)0.0829 (14)0.0636 (11)−0.0025 (11)0.0214 (10)0.0088 (10)
C190.0585 (14)0.0518 (10)0.0526 (9)0.0029 (9)0.0196 (8)0.0003 (8)
C200.0554 (13)0.0495 (10)0.0484 (8)0.0016 (8)0.0215 (8)−0.0003 (7)
C210.0542 (12)0.0591 (11)0.0475 (9)0.0053 (9)0.0217 (8)0.0007 (8)
C220.0566 (13)0.0551 (11)0.0480 (9)0.0021 (9)0.0222 (8)0.0009 (8)
O1—C111.3732 (19)C9—C101.389 (3)
O1—C221.4492 (19)C9—H90.98 (2)
N1—C221.419 (2)C10—H100.99 (2)
N1—C211.483 (2)C11—C201.363 (2)
N1—H10.97 (2)C11—C121.415 (2)
N2—C41.331 (3)C12—C131.359 (3)
N2—C51.332 (2)C12—H120.962 (19)
N3—C81.328 (3)C13—C141.404 (3)
N3—C71.342 (2)C13—H131.017 (18)
C1—C21.374 (2)C14—C151.414 (2)
C1—C51.381 (2)C14—C191.422 (2)
C1—C211.522 (2)C15—C161.341 (3)
C2—C31.384 (3)C15—H151.040 (19)
C2—H21.017 (17)C16—C171.402 (3)
C3—C41.365 (3)C16—H160.97 (2)
C3—H30.95 (2)C17—C181.372 (3)
C4—H40.98 (2)C17—H170.98 (2)
C5—H51.002 (19)C18—C191.409 (3)
C6—C101.374 (2)C18—H180.988 (17)
C6—C71.378 (2)C19—C201.431 (2)
C6—C221.512 (2)C20—C211.520 (2)
C7—H71.02 (2)C21—H210.975 (16)
C8—C91.368 (3)C22—H221.032 (17)
C8—H81.03 (2)
C11—O1—C22113.65 (13)C13—C12—C11119.1 (2)
C22—N1—C21111.52 (12)C13—C12—H12123.7 (10)
C22—N1—H1109.1 (11)C11—C12—H12117.2 (10)
C21—N1—H1113.5 (11)C12—C13—C14121.13 (17)
C4—N2—C5116.46 (18)C12—C13—H13116.8 (11)
C8—N3—C7116.90 (17)C14—C13—H13122.0 (10)
C2—C1—C5116.69 (17)C13—C14—C15121.03 (17)
C2—C1—C21124.50 (16)C13—C14—C19119.30 (15)
C5—C1—C21118.79 (15)C15—C14—C19119.65 (19)
C1—C2—C3119.44 (18)C16—C15—C14121.3 (2)
C1—C2—H2119.6 (10)C16—C15—H15122.1 (11)
C3—C2—H2120.9 (10)C14—C15—H15116.6 (11)
C4—C3—C2119.0 (2)C15—C16—C17119.8 (2)
C4—C3—H3121.6 (14)C15—C16—H16123.2 (14)
C2—C3—H3119.3 (13)C17—C16—H16116.9 (14)
N2—C4—C3123.3 (2)C18—C17—C16120.6 (2)
N2—C4—H4116.1 (12)C18—C17—H17118.8 (13)
C3—C4—H4120.6 (12)C16—C17—H17120.5 (12)
N2—C5—C1125.15 (18)C17—C18—C19121.2 (2)
N2—C5—H5117.1 (11)C17—C18—H18118.3 (10)
C1—C5—H5117.7 (11)C19—C18—H18120.5 (10)
C10—C6—C7117.81 (16)C18—C19—C14117.29 (16)
C10—C6—C22123.44 (15)C18—C19—C20123.26 (16)
C7—C6—C22118.75 (17)C14—C19—C20119.45 (17)
N3—C7—C6124.0 (2)C11—C20—C19118.07 (14)
N3—C7—H7114.2 (10)C11—C20—C21119.66 (14)
C6—C7—H7121.8 (10)C19—C20—C21122.23 (17)
N3—C8—C9123.56 (19)N1—C21—C20111.47 (15)
N3—C8—H8117.4 (12)N1—C21—C1108.81 (14)
C9—C8—H8119.0 (12)C20—C21—C1115.12 (13)
C8—C9—C10118.7 (2)N1—C21—H21105.9 (9)
C8—C9—H9121.3 (11)C20—C21—H21108.8 (9)
C10—C9—H9120.0 (11)C1—C21—H21106.2 (10)
C6—C10—C9119.09 (18)N1—C22—O1113.38 (14)
C6—C10—H10121.0 (11)N1—C22—C6112.33 (12)
C9—C10—H10119.9 (12)O1—C22—C6105.59 (14)
C20—C11—O1123.91 (14)N1—C22—H22108.7 (9)
C20—C11—C12122.79 (15)O1—C22—H22107.5 (8)
O1—C11—C12113.30 (17)C6—C22—H22109.2 (9)
C5—C1—C2—C3−0.3 (3)C13—C14—C19—C18175.59 (17)
C21—C1—C2—C3178.03 (18)C15—C14—C19—C18−2.6 (3)
C1—C2—C3—C41.4 (3)C13—C14—C19—C20−4.4 (2)
C5—N2—C4—C30.1 (3)C15—C14—C19—C20177.40 (16)
C2—C3—C4—N2−1.3 (3)O1—C11—C20—C19−178.17 (14)
C4—N2—C5—C11.0 (3)C12—C11—C20—C192.2 (2)
C2—C1—C5—N2−0.9 (3)O1—C11—C20—C214.2 (2)
C21—C1—C5—N2−179.35 (18)C12—C11—C20—C21−175.39 (15)
C8—N3—C7—C60.7 (3)C18—C19—C20—C11−178.01 (17)
C10—C6—C7—N3−0.6 (3)C14—C19—C20—C111.9 (2)
C22—C6—C7—N3179.19 (17)C18—C19—C20—C21−0.5 (3)
C7—N3—C8—C9−0.1 (3)C14—C19—C20—C21179.47 (16)
N3—C8—C9—C10−0.6 (3)C22—N1—C21—C20−41.2 (2)
C7—C6—C10—C9−0.1 (3)C22—N1—C21—C186.79 (17)
C22—C6—C10—C9−179.90 (17)C11—C20—C21—N110.0 (2)
C8—C9—C10—C60.7 (3)C19—C20—C21—N1−167.51 (15)
C22—O1—C11—C2013.0 (2)C11—C20—C21—C1−114.56 (18)
C22—O1—C11—C12−167.37 (14)C19—C20—C21—C167.9 (2)
C20—C11—C12—C13−3.9 (3)C2—C1—C21—N1−109.53 (19)
O1—C11—C12—C13176.41 (15)C5—C1—C21—N168.8 (2)
C11—C12—C13—C141.3 (3)C2—C1—C21—C2016.4 (3)
C12—C13—C14—C15−179.09 (18)C5—C1—C21—C20−165.26 (17)
C12—C13—C14—C192.7 (3)C21—N1—C22—O161.15 (19)
C13—C14—C15—C16−176.6 (2)C21—N1—C22—C6−179.25 (14)
C19—C14—C15—C161.6 (3)C11—O1—C22—N1−46.19 (18)
C14—C15—C16—C170.5 (4)C11—O1—C22—C6−169.58 (13)
C15—C16—C17—C18−1.6 (4)C10—C6—C22—N1−111.91 (19)
C16—C17—C18—C190.5 (4)C7—C6—C22—N168.3 (2)
C17—C18—C19—C141.6 (3)C10—C6—C22—O112.1 (2)
C17—C18—C19—C20−178.5 (2)C7—C6—C22—O1−167.64 (15)
D—H···AD—HH···AD···AD—H···A
N1—H1···N3i0.98 (2)2.04 (2)3.009 (2)170.7 (17)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯N3i0.98 (2)2.04 (2)3.009 (2)170.7 (17)

Symmetry code: (i) .

  2 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 new 1,3-disubstituted-2,3-dihydro-1H-naphth[1,2e][1,3]oxazines.

Authors:  Zuhal Turgut; Emel Pelit; Adem Köycü
Journal:  Molecules       Date:  2007-03-07       Impact factor: 4.411
  2 in total
  1 in total

1.  8-Bromo-1,3-diphenyl-2,3-dihydro-1H-naphtho-[1,2-e][1,3]oxazine.

Authors:  Jerry P Jasinski; Albert E Pek; A N Mayekar; H S Yathirajan; B Narayana
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-07-17
  1 in total

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