Literature DB >> 21522655

2-[(E)-(4-Methyl-phen-yl)imino-meth-yl]-6-(morpholin-4-ylmeth-yl)phenol.

Mehmet Akkurt, Sevim Türktekin, Aliasghar Jarrahpour, Hashem Sharghi, Seid Ali Torabi Badrabady, Mahdi Aberi, Orhan Büyükgüngör.   

Abstract

In the title compound, C(19)H(22)N(2)O(2), the morpholine ring adopts an almost perfect normal chair conformation with puckering parameters Q(T), θ and ϕ of 0.5642 (18) Å, 177.32 (17) and ϕ = 10 (4)°, respectively. The two benzene rings make a dihedral angle of 42.67 (8)° with each other. An intra-molecular O-H⋯N hydrogen bond helps to stabilize the mol-ecular conformation. Aromatic C-H⋯π inter-actions and π-π stacking inter-actions [centroid-centroid distance = 3.6155 (15) Å] between the benzene rings contribute to the stabilization of the crystal structure.

Entities:  

Year:  2010        PMID： 21522655      PMCID： PMC3050317          DOI： 10.1107/S1600536810052311

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


Related literature

For general background to Schiff bases with an azomethine or imine group (—C=N—), see: Akkurt et al. (2008 ▶); Dhar & Taploo (1982 ▶); Emregül et al. (2006 ▶); Jarrahpour & Khalili (2006 ▶); Jarrahpour et al. (2007 ▶); Mladenova et al. (2002 ▶); Przybylski et al. (2009 ▶); Sessler et al. (2006 ▶); Singh et al. (2006 ▶). For a similar structure, see: Akkurt et al. (2008 ▶). For reference structural data, see: Allen et al. (1987 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H22N2O2 M = 310.39 Triclinic, a = 9.807 (3) Å b = 10.091 (3) Å c = 10.528 (3) Å α = 99.78 (2)° β = 109.34 (2)° γ = 115.18 (2)° V = 828.7 (5) Å3 Z = 2 Mo Kα radiation μ = 0.08 mm−1 T = 296 K 0.53 × 0.40 × 0.23 mm

Data collection

Stoe IPDS 2 diffractometer Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.958, T max = 0.982 15421 measured reflections 3443 independent reflections 2894 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.121 S = 1.08 3443 reflections 208 parameters H-atom parameters constrained Δρmax = 0.19 e Å−3 Δρmin = −0.17 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: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052311/si2317sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052311/si2317Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H22N2O2Z = 2
Mr = 310.39F(000) = 332
Triclinic, P1Dx = 1.244 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.807 (3) ÅCell parameters from 2924 reflections
b = 10.091 (3) Åθ = 2.2–28.0°
c = 10.528 (3) ŵ = 0.08 mm−1
α = 99.78 (2)°T = 296 K
β = 109.34 (2)°Prism, yellow
γ = 115.18 (2)°0.53 × 0.40 × 0.23 mm
V = 828.7 (5) Å3
Stoe IPDS 2 diffractometer3443 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2894 reflections with I > 2σ(I)
plane graphiteRint = 0.026
Detector resolution: 6.67 pixels mm-1θmax = 26.5°, θmin = 2.2°
ω scansh = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)k = −12→12
Tmin = 0.958, Tmax = 0.982l = −13→13
15421 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0601P)2 + 0.1054P] where P = (Fo2 + 2Fc2)/3
3443 reflections(Δ/σ)max < 0.001
208 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
O10.68415 (12)0.65889 (11)0.31759 (10)0.0605 (3)
O20.25927 (15)−0.05310 (13)0.37129 (14)0.0731 (4)
N10.70908 (14)0.89705 (12)0.23661 (12)0.0509 (3)
N20.39377 (13)0.18806 (12)0.26385 (12)0.0470 (3)
C10.80432 (16)1.05345 (14)0.24513 (14)0.0460 (4)
C20.90410 (18)1.17249 (16)0.38095 (15)0.0529 (4)
C31.00285 (17)1.32583 (15)0.39579 (15)0.0541 (4)
C41.00833 (16)1.36570 (15)0.27667 (15)0.0508 (4)
C50.90948 (17)1.24557 (15)0.14201 (15)0.0515 (4)
C60.80862 (16)1.09138 (14)0.12519 (14)0.0492 (4)
C71.1219 (2)1.53245 (17)0.29286 (19)0.0719 (5)
C80.56247 (17)0.80217 (15)0.13084 (15)0.0496 (4)
C90.46275 (16)0.63836 (14)0.11187 (14)0.0464 (4)
C100.52758 (16)0.57282 (14)0.20561 (13)0.0461 (4)
C110.43183 (16)0.41315 (14)0.18260 (14)0.0469 (4)
C120.27222 (17)0.32268 (15)0.06675 (15)0.0503 (4)
C130.20689 (17)0.38570 (16)−0.02683 (15)0.0538 (4)
C140.30183 (17)0.54185 (16)−0.00456 (15)0.0529 (4)
C150.51246 (18)0.34623 (16)0.28015 (16)0.0565 (4)
C160.48127 (18)0.10773 (17)0.31696 (16)0.0555 (5)
C170.3568 (2)−0.05472 (17)0.29914 (17)0.0625 (5)
C180.1757 (2)0.0270 (2)0.3227 (2)0.0783 (7)
C190.2971 (2)0.19116 (18)0.34212 (18)0.0620 (5)
H10.728400.749900.320900.0910*
H20.904201.148400.462400.0630*
H31.067101.404200.487200.0650*
H50.911101.269400.060800.0620*
H60.743701.013200.033600.0590*
H7A1.237401.566000.352300.0860*
H7B1.092301.600300.337200.0860*
H7C1.108101.536900.199300.0860*
H80.517700.839400.063200.0600*
H120.207000.216900.051100.0600*
H130.099400.32250−0.104200.0650*
H140.258400.58370−0.067800.0630*
H15A0.601100.344300.259600.0680*
H15B0.564600.415300.379800.0680*
H16A0.561300.167300.418200.0670*
H16B0.543600.101200.263800.0670*
H17A0.28230−0.116000.197100.0750*
H17B0.41730−0.105400.336600.0750*
H18A0.112600.030900.375900.0940*
H18B0.09590−0.031100.221200.0940*
H19A0.235300.241500.306600.0740*
H19B0.373300.251700.444000.0740*
U11U22U33U12U13U23
O10.0572 (6)0.0439 (5)0.0533 (5)0.0144 (4)0.0117 (4)0.0177 (4)
O20.0841 (8)0.0696 (7)0.0967 (8)0.0459 (6)0.0539 (7)0.0551 (6)
N10.0570 (7)0.0382 (5)0.0558 (6)0.0216 (5)0.0276 (5)0.0173 (5)
N20.0482 (6)0.0411 (5)0.0550 (6)0.0236 (5)0.0240 (5)0.0224 (5)
C10.0463 (6)0.0371 (6)0.0536 (7)0.0211 (5)0.0225 (5)0.0160 (5)
C20.0569 (8)0.0476 (7)0.0503 (7)0.0247 (6)0.0234 (6)0.0174 (6)
C30.0514 (7)0.0434 (7)0.0511 (7)0.0203 (6)0.0157 (6)0.0082 (5)
C40.0447 (7)0.0383 (6)0.0602 (8)0.0189 (5)0.0184 (6)0.0156 (5)
C50.0531 (7)0.0445 (7)0.0542 (7)0.0225 (6)0.0237 (6)0.0207 (6)
C60.0499 (7)0.0396 (6)0.0486 (7)0.0193 (5)0.0192 (6)0.0120 (5)
C70.0678 (10)0.0419 (7)0.0777 (10)0.0143 (7)0.0231 (8)0.0184 (7)
C80.0541 (7)0.0432 (7)0.0566 (7)0.0257 (6)0.0280 (6)0.0218 (6)
C90.0490 (7)0.0404 (6)0.0527 (7)0.0218 (5)0.0269 (6)0.0188 (5)
C100.0473 (7)0.0406 (6)0.0444 (6)0.0186 (5)0.0206 (5)0.0138 (5)
C110.0502 (7)0.0410 (6)0.0506 (7)0.0216 (5)0.0256 (6)0.0190 (5)
C120.0487 (7)0.0384 (6)0.0585 (8)0.0177 (5)0.0249 (6)0.0183 (5)
C130.0436 (7)0.0474 (7)0.0583 (8)0.0180 (6)0.0174 (6)0.0196 (6)
C140.0504 (7)0.0511 (7)0.0605 (8)0.0268 (6)0.0246 (6)0.0271 (6)
C150.0509 (7)0.0475 (7)0.0601 (8)0.0194 (6)0.0192 (6)0.0240 (6)
C160.0567 (8)0.0581 (8)0.0620 (8)0.0354 (7)0.0271 (7)0.0282 (6)
C170.0816 (10)0.0525 (8)0.0645 (9)0.0414 (8)0.0325 (8)0.0284 (7)
C180.0730 (10)0.0819 (11)0.1191 (15)0.0480 (9)0.0605 (11)0.0659 (11)
C190.0761 (10)0.0610 (8)0.0774 (10)0.0451 (8)0.0470 (8)0.0364 (7)
O1—C101.3492 (18)C16—C171.501 (2)
O2—C171.408 (3)C18—C191.500 (3)
O2—C181.419 (3)C2—H20.9300
O1—H10.8200C3—H30.9300
N1—C81.277 (2)C5—H50.9300
N1—C11.4189 (19)C6—H60.9300
N2—C151.458 (2)C7—H7A0.9600
N2—C161.461 (2)C7—H7B0.9600
N2—C191.454 (3)C7—H7C0.9600
C1—C21.391 (2)C8—H80.9300
C1—C61.3887 (19)C12—H120.9300
C2—C31.378 (2)C13—H130.9300
C3—C41.391 (2)C14—H140.9300
C4—C71.511 (2)C15—H15A0.9700
C4—C51.388 (2)C15—H15B0.9700
C5—C61.383 (2)C16—H16A0.9700
C8—C91.453 (2)C16—H16B0.9700
C9—C101.407 (2)C17—H17A0.9700
C9—C141.395 (2)C17—H17B0.9700
C10—C111.402 (2)C18—H18A0.9700
C11—C151.513 (2)C18—H18B0.9700
C11—C121.383 (2)C19—H19A0.9700
C12—C131.388 (2)C19—H19B0.9700
C13—C141.373 (2)
O1···N12.6261 (18)H6···C82.7300
O2···N22.852 (2)H6···H82.3300
O1···H15B2.5400H6···N2ii2.9100
O1···H19Bi2.8300H7C···H52.3500
O1···H15A2.8200H8···C62.6600
O2···H2i2.7700H8···H62.3300
N1···O12.6261 (18)H8···H142.4300
N2···O22.852 (2)H12···N22.5300
N1···H11.9000H12···C192.9800
N2···H122.5300H12···H19A2.5700
N2···H6ii2.9100H13···H18Bvii2.5000
C1···C18iii3.596 (3)H14···H82.4300
C8···C12ii3.409 (3)H14···C5vi2.8800
C10···C14ii3.432 (3)H15A···O12.8200
C12···C8ii3.409 (3)H15A···H16B2.2800
C12···C193.368 (2)H15B···O12.5400
C14···C10ii3.432 (3)H15B···H16A2.5900
C18···C1iv3.596 (3)H15B···H19B2.3000
C19···C123.368 (2)H16A···H15B2.5900
C1···H16Bv2.8600H16A···H19B2.4100
C1···H18Aiii3.0000H16B···C1viii2.8600
C2···H18Aiii2.9600H16B···C2viii3.0300
C2···H16Bv3.0300H16B···H15A2.2800
C3···H19Aiii3.1000H17A···H18B2.3900
C4···H19Aiii2.9400H17A···H5ii2.4600
C5···H14vi2.8800H18A···C1iv3.0000
C6···H82.6600H18A···C2iv2.9600
C8···H12.4200H18B···H17A2.3900
C8···H62.7300H18B···H13vii2.5000
C11···H19A2.8300H19A···C3iv3.1000
C12···H19A2.8700H19A···C4iv2.9400
C19···H122.9800H19A···C112.8300
H1···N11.9000H19A···C122.8700
H1···C82.4200H19A···H122.5700
H2···O2i2.7700H19B···H15B2.3000
H5···H7C2.3500H19B···H16A2.4100
H5···H17Aii2.4600H19B···O1i2.8300
C17—O2—C18110.04 (14)C5—C6—H6120.00
C10—O1—H1109.00C4—C7—H7A109.00
C1—N1—C8120.07 (13)C4—C7—H7B109.00
C15—N2—C19111.36 (13)C4—C7—H7C109.00
C16—N2—C19108.24 (13)H7A—C7—H7B110.00
C15—N2—C16111.27 (14)H7A—C7—H7C109.00
N1—C1—C6122.95 (12)H7B—C7—H7C109.00
C2—C1—C6118.83 (13)N1—C8—H8119.00
N1—C1—C2118.13 (12)C9—C8—H8119.00
C1—C2—C3120.53 (13)C11—C12—H12119.00
C2—C3—C4121.30 (13)C13—C12—H12119.00
C3—C4—C5117.56 (14)C12—C13—H13120.00
C5—C4—C7120.84 (14)C14—C13—H13120.00
C3—C4—C7121.57 (13)C9—C14—H14120.00
C4—C5—C6121.83 (13)C13—C14—H14120.00
C1—C6—C5119.93 (13)N2—C15—H15A109.00
N1—C8—C9122.64 (14)N2—C15—H15B109.00
C8—C9—C10121.32 (13)C11—C15—H15A109.00
C8—C9—C14119.69 (13)C11—C15—H15B109.00
C10—C9—C14118.95 (13)H15A—C15—H15B108.00
O1—C10—C11117.69 (13)N2—C16—H16A110.00
C9—C10—C11120.53 (13)N2—C16—H16B110.00
O1—C10—C9121.76 (13)C17—C16—H16A110.00
C10—C11—C12118.40 (13)C17—C16—H16B110.00
C12—C11—C15123.20 (13)H16A—C16—H16B108.00
C10—C11—C15118.29 (13)O2—C17—H17A109.00
C11—C12—C13121.68 (14)O2—C17—H17B109.00
C12—C13—C14119.68 (15)C16—C17—H17A109.00
C9—C14—C13120.76 (14)C16—C17—H17B109.00
N2—C15—C11113.61 (14)H17A—C17—H17B108.00
N2—C16—C17110.36 (15)O2—C18—H18A109.00
O2—C17—C16112.22 (15)O2—C18—H18B109.00
O2—C18—C19112.08 (17)C19—C18—H18A109.00
N2—C19—C18110.12 (15)C19—C18—H18B109.00
C1—C2—H2120.00H18A—C18—H18B108.00
C3—C2—H2120.00N2—C19—H19A110.00
C2—C3—H3119.00N2—C19—H19B110.00
C4—C3—H3119.00C18—C19—H19A110.00
C4—C5—H5119.00C18—C19—H19B110.00
C6—C5—H5119.00H19A—C19—H19B108.00
C1—C6—H6120.00
C17—O2—C18—C19−56.61 (19)N1—C8—C9—C10−3.8 (3)
C18—O2—C17—C1656.19 (18)N1—C8—C9—C14178.64 (17)
C8—N1—C1—C6−39.4 (3)C10—C9—C14—C130.8 (3)
C8—N1—C1—C2143.89 (18)C14—C9—C10—C11−0.2 (2)
C1—N1—C8—C9176.53 (15)C8—C9—C10—O10.5 (2)
C19—N2—C15—C11−79.79 (16)C14—C9—C10—O1178.05 (15)
C15—N2—C16—C17−180.00 (13)C8—C9—C14—C13178.35 (16)
C16—N2—C15—C11159.35 (13)C8—C9—C10—C11−177.71 (15)
C15—N2—C19—C18179.71 (14)C9—C10—C11—C12−0.6 (2)
C19—N2—C16—C1757.33 (16)O1—C10—C11—C15−2.6 (2)
C16—N2—C19—C18−57.68 (17)O1—C10—C11—C12−178.89 (15)
N1—C1—C6—C5−177.41 (17)C9—C10—C11—C15175.65 (15)
N1—C1—C2—C3178.14 (17)C12—C11—C15—N2−14.1 (2)
C2—C1—C6—C5−0.7 (3)C10—C11—C15—N2169.80 (14)
C6—C1—C2—C31.3 (3)C15—C11—C12—C13−175.25 (16)
C1—C2—C3—C4−1.2 (3)C10—C11—C12—C130.8 (3)
C2—C3—C4—C50.6 (3)C11—C12—C13—C14−0.2 (3)
C2—C3—C4—C7−177.38 (18)C12—C13—C14—C9−0.6 (3)
C3—C4—C5—C60.0 (3)N2—C16—C17—O2−57.79 (17)
C7—C4—C5—C6177.97 (18)O2—C18—C19—N258.52 (19)
C4—C5—C6—C10.1 (3)
Cg2 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.902.6261 (18)147
C12—H12···N20.932.532.876 (2)102
C19—H19A···Cg2iv0.972.963.732 (3)137
Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯N10.821.902.6261 (18)147
C19—H19A⋯Cg2i0.972.963.732 (3)137

Symmetry code: (i) .

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