Literature DB >> 24046605

(E)-N-(3,3-Di-phenyl-allyl-idene)naph-thal-en-1-amine.

Jae Kyun Lee1, Kee Dal Nam, Joo Hwan Cha, Yong Seo Cho, Joon Kyun Lee.   

Abstract

The title compound, C25H19N, adopts an E conformation about the C=N bond. The naphthalene ring system and the phenyl rings form dihedral angles 38.1 (1), 46.9 (8) and 48.5 (1)°, respectively, with the mean plane of the central enimino fragment. The crystal packing exhibits no directional close contacts.

Entities:  

Year:  2013        PMID： 24046605      PMCID： PMC3772462          DOI： 10.1107/S1600536813014888

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


Related literature

For the crystal structures of related compounds studied recently by our group, see: Cha et al. (2012 ▶); Kang et al. (2012 ▶); Yu et al. (2013 ▶); Nam et al. (2013 ▶).

Experimental

Crystal data

C25H19N M = 333.41 Orthorhombic, a = 11.2203 (7) Å b = 13.5658 (7) Å c = 24.1946 (13) Å V = 3682.7 (4) Å3 Z = 8 Mo Kα radiation μ = 0.07 mm−1 T = 296 K 0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.986, T max = 0.986 33578 measured reflections 4190 independent reflections 2080 reflections with I > 2σ(I) R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.061 wR(F 2) = 0.197 S = 0.95 4190 reflections 235 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.25 e Å−3 Data collection: RAPID-AUTO (Rigaku, 2006 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014888/cv5411sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014888/cv5411Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813014888/cv5411Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H19NZ = 8
Mr = 333.41F(000) = 1408
Orthorhombic, PbcaDx = 1.203 Mg m−3
Hall symbol: -P 2ac 2abMo Kα radiation, λ = 0.71075 Å
a = 11.2203 (7) ŵ = 0.07 mm−1
b = 13.5658 (7) ÅT = 296 K
c = 24.1946 (13) ÅBlock, yellow
V = 3682.7 (4) Å30.20 × 0.20 × 0.20 mm
Rigaku R-AXIS RAPID diffractometer4190 independent reflections
Radiation source: fine-focus sealed tube2080 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
Detector resolution: 10.000 pixels mm-1θmax = 27.4°, θmin = 3.0°
ω scansh = −14→14
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)k = −17→17
Tmin = 0.986, Tmax = 0.986l = −31→30
33578 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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 0.95w = 1/[σ2(Fo2) + (0.1186P)2] where P = (Fo2 + 2Fc2)/3
4190 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.25 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
N10.03605 (16)0.37399 (12)0.86987 (6)0.0588 (5)
C1−0.1297 (2)0.27203 (18)0.83686 (9)0.0688 (6)
H1−0.11430.22510.86400.083*
C2−0.2224 (3)0.2562 (2)0.79886 (10)0.0830 (8)
H2−0.26820.19920.80130.100*
C3−0.2458 (2)0.3231 (2)0.75873 (9)0.0827 (8)
H3−0.30790.31180.73410.099*
C4−0.1772 (2)0.4100 (2)0.75384 (8)0.0682 (7)
C5−0.1976 (3)0.4814 (3)0.71211 (10)0.0888 (9)
H5−0.25690.47050.68600.107*
C6−0.1321 (3)0.5650 (3)0.70969 (10)0.0947 (10)
H6−0.14710.61080.68190.114*
C7−0.0421 (3)0.5836 (2)0.74842 (11)0.0850 (8)
H70.00180.64160.74650.102*
C8−0.0190 (2)0.51646 (18)0.78898 (9)0.0690 (7)
H80.04060.52950.81470.083*
C9−0.0839 (2)0.42754 (17)0.79262 (8)0.0582 (6)
C10−0.06209 (19)0.35522 (16)0.83444 (8)0.0564 (5)
C110.0290 (2)0.35090 (15)0.92139 (8)0.0558 (5)
H11−0.03940.32130.93540.067*
C120.1286 (2)0.37159 (14)0.95689 (8)0.0562 (5)
H120.19790.39230.93930.067*
C130.13445 (18)0.36485 (14)1.01268 (8)0.0522 (5)
C140.03384 (19)0.33393 (15)1.04830 (8)0.0534 (5)
C15−0.0793 (2)0.37540 (16)1.04349 (9)0.0630 (6)
H15−0.09370.42271.01650.076*
C16−0.1706 (2)0.3467 (2)1.07863 (10)0.0761 (7)
H16−0.24570.37501.07510.091*
C17−0.1506 (3)0.2765 (2)1.11871 (10)0.0793 (8)
H17−0.21220.25711.14200.095*
C18−0.0399 (3)0.23538 (18)1.12413 (9)0.0747 (7)
H18−0.02640.18811.15130.090*
C190.0517 (2)0.26348 (16)1.08965 (8)0.0642 (6)
H190.12660.23511.09390.077*
C200.24624 (19)0.39592 (14)1.04092 (8)0.0522 (5)
C210.2411 (2)0.45116 (16)1.08939 (8)0.0655 (6)
H210.16760.46351.10580.079*
C220.3434 (3)0.48772 (19)1.11332 (10)0.0760 (7)
H220.33850.52571.14520.091*
C230.4527 (3)0.46821 (19)1.09016 (10)0.0781 (7)
H230.52160.49331.10620.094*
C240.4600 (2)0.41132 (18)1.04309 (10)0.0702 (6)
H240.53400.39691.02790.084*
C250.3577 (2)0.37575 (16)1.01848 (8)0.0604 (6)
H250.36340.33790.98650.072*
U11U22U33U12U13U23
N10.0562 (11)0.0734 (12)0.0467 (9)0.0012 (9)−0.0046 (8)0.0029 (8)
C10.0738 (16)0.0759 (15)0.0568 (12)−0.0053 (13)−0.0020 (11)−0.0047 (11)
C20.0819 (19)0.0996 (19)0.0675 (15)−0.0148 (15)−0.0064 (14)−0.0201 (14)
C30.0614 (16)0.127 (2)0.0593 (13)0.0046 (16)−0.0104 (12)−0.0266 (15)
C40.0574 (15)0.1024 (18)0.0447 (11)0.0215 (13)−0.0033 (10)−0.0105 (12)
C50.080 (2)0.133 (3)0.0530 (13)0.042 (2)−0.0055 (13)−0.0045 (15)
C60.108 (3)0.119 (2)0.0568 (15)0.052 (2)0.0038 (15)0.0169 (16)
C70.087 (2)0.0966 (18)0.0716 (15)0.0220 (15)0.0105 (14)0.0225 (14)
C80.0638 (15)0.0851 (17)0.0580 (13)0.0107 (13)0.0052 (11)0.0094 (12)
C90.0501 (13)0.0809 (15)0.0436 (10)0.0106 (11)0.0032 (9)−0.0022 (10)
C100.0531 (13)0.0728 (14)0.0432 (10)0.0037 (11)−0.0006 (9)−0.0030 (9)
C110.0597 (13)0.0604 (12)0.0473 (10)−0.0005 (10)−0.0016 (9)0.0012 (9)
C120.0552 (13)0.0609 (13)0.0524 (11)−0.0005 (10)−0.0043 (10)0.0020 (9)
C130.0575 (13)0.0496 (11)0.0494 (10)0.0035 (9)−0.0017 (9)−0.0002 (9)
C140.0587 (13)0.0538 (11)0.0477 (10)0.0004 (10)−0.0015 (9)−0.0044 (9)
C150.0639 (15)0.0627 (13)0.0623 (12)0.0056 (11)0.0012 (11)−0.0043 (10)
C160.0628 (16)0.0831 (16)0.0824 (16)0.0050 (13)0.0132 (13)−0.0138 (14)
C170.083 (2)0.0854 (18)0.0691 (14)−0.0109 (15)0.0213 (14)−0.0095 (13)
C180.0897 (19)0.0763 (16)0.0580 (13)−0.0081 (14)0.0090 (13)0.0040 (11)
C190.0681 (15)0.0682 (13)0.0563 (12)−0.0009 (11)−0.0006 (11)0.0054 (10)
C200.0568 (13)0.0519 (11)0.0480 (10)−0.0005 (10)−0.0030 (9)0.0045 (8)
C210.0706 (15)0.0692 (14)0.0568 (12)−0.0008 (12)−0.0029 (11)−0.0056 (10)
C220.089 (2)0.0747 (16)0.0643 (14)−0.0092 (14)−0.0104 (14)−0.0122 (12)
C230.0777 (19)0.0796 (16)0.0770 (16)−0.0184 (14)−0.0201 (14)0.0043 (13)
C240.0618 (15)0.0793 (16)0.0696 (14)−0.0057 (12)−0.0055 (12)0.0098 (12)
C250.0607 (14)0.0658 (13)0.0547 (12)0.0016 (11)−0.0020 (10)0.0003 (10)
N1—C111.288 (2)C13—C141.481 (3)
N1—C101.419 (3)C13—C201.489 (3)
C1—C101.361 (3)C14—C151.394 (3)
C1—C21.405 (3)C14—C191.398 (3)
C1—H10.9300C15—C161.387 (3)
C2—C31.355 (4)C15—H150.9300
C2—H20.9300C16—C171.377 (4)
C3—C41.412 (4)C16—H160.9300
C3—H30.9300C17—C181.368 (4)
C4—C51.417 (4)C17—H170.9300
C4—C91.425 (3)C18—C191.378 (3)
C5—C61.353 (4)C18—H180.9300
C5—H50.9300C19—H190.9300
C6—C71.400 (4)C20—C251.391 (3)
C6—H60.9300C20—C211.393 (3)
C7—C81.364 (3)C21—C221.379 (3)
C7—H70.9300C21—H210.9300
C8—C91.412 (3)C22—C231.373 (3)
C8—H80.9300C22—H220.9300
C9—C101.430 (3)C23—C241.378 (3)
C11—C121.437 (3)C23—H230.9300
C11—H110.9300C24—C251.380 (3)
C12—C131.355 (3)C24—H240.9300
C12—H120.9300C25—H250.9300
C11—N1—C10119.57 (18)C12—C13—C20118.61 (19)
C10—C1—C2120.7 (2)C14—C13—C20117.07 (16)
C10—C1—H1119.6C15—C14—C19117.8 (2)
C2—C1—H1119.6C15—C14—C13122.11 (19)
C3—C2—C1120.7 (3)C19—C14—C13120.05 (19)
C3—C2—H2119.7C16—C15—C14120.5 (2)
C1—C2—H2119.7C16—C15—H15119.7
C2—C3—C4120.9 (2)C14—C15—H15119.7
C2—C3—H3119.6C17—C16—C15120.4 (2)
C4—C3—H3119.6C17—C16—H16119.8
C3—C4—C5122.8 (2)C15—C16—H16119.8
C3—C4—C9119.0 (2)C18—C17—C16119.8 (2)
C5—C4—C9118.2 (3)C18—C17—H17120.1
C6—C5—C4121.1 (3)C16—C17—H17120.1
C6—C5—H5119.5C17—C18—C19120.4 (2)
C4—C5—H5119.5C17—C18—H18119.8
C5—C6—C7120.9 (3)C19—C18—H18119.8
C5—C6—H6119.6C18—C19—C14121.0 (2)
C7—C6—H6119.6C18—C19—H19119.5
C8—C7—C6119.9 (3)C14—C19—H19119.5
C8—C7—H7120.0C25—C20—C21118.2 (2)
C6—C7—H7120.0C25—C20—C13121.51 (17)
C7—C8—C9121.1 (2)C21—C20—C13120.2 (2)
C7—C8—H8119.4C22—C21—C20120.8 (2)
C9—C8—H8119.4C22—C21—H21119.6
C8—C9—C4118.7 (2)C20—C21—H21119.6
C8—C9—C10122.8 (2)C23—C22—C21120.2 (2)
C4—C9—C10118.5 (2)C23—C22—H22119.9
C1—C10—N1123.73 (19)C21—C22—H22119.9
C1—C10—C9120.2 (2)C22—C23—C24119.9 (2)
N1—C10—C9115.94 (19)C22—C23—H23120.1
N1—C11—C12118.9 (2)C24—C23—H23120.1
N1—C11—H11120.6C23—C24—C25120.2 (2)
C12—C11—H11120.6C23—C24—H24119.9
C13—C12—C11128.3 (2)C25—C24—H24119.9
C13—C12—H12115.8C24—C25—C20120.7 (2)
C11—C12—H12115.8C24—C25—H25119.7
C12—C13—C14124.21 (19)C20—C25—H25119.7
C10—C1—C2—C30.5 (4)C11—C12—C13—C20−176.53 (18)
C1—C2—C3—C40.5 (4)C12—C13—C14—C15−49.7 (3)
C2—C3—C4—C5179.2 (2)C20—C13—C14—C15126.6 (2)
C2—C3—C4—C9−1.3 (3)C12—C13—C14—C19132.6 (2)
C3—C4—C5—C6178.1 (2)C20—C13—C14—C19−51.1 (3)
C9—C4—C5—C6−1.4 (4)C19—C14—C15—C16−0.4 (3)
C4—C5—C6—C70.0 (4)C13—C14—C15—C16−178.12 (19)
C5—C6—C7—C80.5 (4)C14—C15—C16—C17−0.2 (3)
C6—C7—C8—C90.4 (4)C15—C16—C17—C180.4 (4)
C7—C8—C9—C4−1.7 (3)C16—C17—C18—C19−0.2 (4)
C7—C8—C9—C10179.8 (2)C17—C18—C19—C14−0.3 (4)
C3—C4—C9—C8−177.3 (2)C15—C14—C19—C180.6 (3)
C5—C4—C9—C82.2 (3)C13—C14—C19—C18178.42 (19)
C3—C4—C9—C101.2 (3)C12—C13—C20—C25−38.9 (3)
C5—C4—C9—C10−179.31 (19)C14—C13—C20—C25144.7 (2)
C2—C1—C10—N1−177.1 (2)C12—C13—C20—C21137.5 (2)
C2—C1—C10—C9−0.6 (3)C14—C13—C20—C21−38.9 (3)
C11—N1—C10—C1−40.3 (3)C25—C20—C21—C222.3 (3)
C11—N1—C10—C9143.1 (2)C13—C20—C21—C22−174.3 (2)
C8—C9—C10—C1178.2 (2)C20—C21—C22—C23−1.4 (4)
C4—C9—C10—C1−0.2 (3)C21—C22—C23—C24−0.5 (4)
C8—C9—C10—N1−5.0 (3)C22—C23—C24—C251.4 (4)
C4—C9—C10—N1176.55 (18)C23—C24—C25—C20−0.5 (3)
C10—N1—C11—C12−179.19 (18)C21—C20—C25—C24−1.3 (3)
N1—C11—C12—C13171.0 (2)C13—C20—C25—C24175.22 (19)
C11—C12—C13—C14−0.3 (3)
  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.  (E)-N-(3,3-Diphenyl-allyl-idene)-3-nitro-aniline.

Authors:  Joo Hwan Cha; Yong Koo Kang; Yong Seo Cho; Jae Kyun Lee; Jae Choon Woo
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-29

3.  (E)-N-(3,3-Diphenyl-allyl-idene)-4-nitro-aniline.

Authors:  Yong Koo Kang; Yong Seo Cho; Jae Kyun Lee; Byung-Yong Yu; Joo Hwan Cha
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-09-29

4.  (E)-N-[(E)-3-(4-Nitro-phen-yl)allyl-idene]naphthalen-1-amine.

Authors:  Kee Dal Nam; Joo Hwan Cha; Yong Seo Cho; Jae Kyun Lee; Ae Nim Pae
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-03-16

5.  (E)-N-(3,3-Di-phenyl-allyl-idene)-2-(tri-fluoro-meth-yl)aniline.

Authors:  Byung-Yong Yu; Ji Eun Lee; Yong Seo Cho; Joo Hwan Cha; Jae Kyun Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-04-20
  5 in total
  1 in total

1.  Crystal structure of (E)-N-[(E)-3-(4-meth-oxy-phen-yl)allyl-idene]naphthalen-1-amine.

Authors:  Jae Kyun Lee; Joo Hwan Cha; Yong Seo Cho; Sun-Joon Min; Joon Kyun Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2014-10-24
  1 in total

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