Literature DB >> 25484813

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

Jae Kyun Lee1, Joo Hwan Cha2, Yong Seo Cho1, Sun-Joon Min1, Joon Kyun Lee3.   

Abstract

In the title compound, C20H17NO, the dihedral angle between the mean planes of the 4-meth-oxy-phenyl ring and the naphthalene ring is 69.50 (7)°. The meth-oxy group is almost coplanar with the benzene ring to which it is connected [Cb-Cb-Om-Cm torsion angle of -7.9 (2)°; b = benzene and m = meth-oxy] and the imine group displays a C-C-N=C torsion angle is -57.2 (2)°. The imine (C=N) group has an E conformation. In the crystal, weak π-π inter-actions between the benzene rings [centroid-centroid distance = 3.7781 (10) Å] are observed.

Entities:  

Keywords:  crystal structure; naphthalene derivative; π–π inter­actions

Year:  2014        PMID： 25484813      PMCID： PMC4257298          DOI： 10.1107/S1600536814022521

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


Related literature

For the uses of naphthalene derivatives in various scientific fields, see: Ohta et al. (2005 ▶) and references therein. For background information and related crystal structures studied recently by our group, see: Lee et al. (2013 ▶); Nam et al. (2013 ▶).

Experimental

Crystal data

C20H17NO M = 287.36 Triclinic, a = 7.8278 (8) Å b = 9.8931 (10) Å c = 11.3929 (13) Å α = 69.307 (3)° β = 73.561 (3)° γ = 81.375 (3)° V = 790.40 (15) Å3 Z = 2 Mo Kα radiation μ = 0.07 mm−1 T = 296 K 0.30 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.701, T max = 0.985 7842 measured reflections 3584 independent reflections 1680 reflections with F 2 > 2σ(F 2) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.119 S = 0.99 3584 reflections 212 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.15 e Å−3 Δρmin = −0.23 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2006 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); 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) General, I. DOI: 10.1107/S1600536814022521/ff2132sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814022521/ff2132Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814022521/ff2132Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814022521/ff2132fig1.tif The mol­ecular structure of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. CCDC reference: 1029010 Additional supporting information: crystallographic information; 3D view; checkCIF report
C20H17NOZ = 2
Mr = 287.36F(000) = 304.00
Triclinic, P1Dx = 1.207 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71075 Å
a = 7.8278 (8) ÅCell parameters from 4416 reflections
b = 9.8931 (10) Åθ = 3.2–27.5°
c = 11.3929 (13) ŵ = 0.07 mm−1
α = 69.307 (3)°T = 296 K
β = 73.561 (3)°Block, yellow
γ = 81.375 (3)°0.30 × 0.20 × 0.20 mm
V = 790.40 (15) Å3
Rigaku R-AXIS RAPID diffractometer1680 reflections with F2 > 2σ(F2)
Detector resolution: 10.000 pixels mm-1Rint = 0.023
ω scansθmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)h = −10→10
Tmin = 0.701, Tmax = 0.985k = −12→12
7842 measured reflectionsl = −14→14
3584 independent reflections
Refinement on F2Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 0.99w = 1/[σ2(Fo2) + (0.059P)2] where P = (Fo2 + 2Fc2)/3
3584 reflections(Δ/σ)max < 0.001
212 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods
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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
xyzUiso*/Ueq
O10.89882 (16)−0.21021 (11)0.81880 (12)0.0803 (4)
N10.41441 (15)0.54539 (14)0.29989 (12)0.0598 (4)
C10.4683 (2)0.68327 (18)0.06861 (16)0.0680 (5)
C20.4038 (3)0.77286 (19)−0.03750 (16)0.0747 (5)
C30.2272 (3)0.80938 (18)−0.02523 (16)0.0705 (5)
C40.10408 (19)0.75954 (15)0.09645 (14)0.0564 (4)
C5−0.0813 (3)0.79622 (18)0.11416 (17)0.0725 (5)
C6−0.1958 (2)0.7484 (2)0.23285 (19)0.0782 (5)
C7−0.1328 (2)0.66267 (18)0.34010 (17)0.0721 (5)
C80.04414 (19)0.62462 (16)0.32731 (15)0.0599 (4)
C90.16784 (17)0.67163 (14)0.20559 (13)0.0491 (4)
C100.35441 (18)0.63154 (15)0.18883 (14)0.0537 (4)
C110.50541 (19)0.42769 (17)0.29784 (16)0.0599 (4)
C120.57334 (18)0.33343 (17)0.40571 (17)0.0596 (4)
C130.64317 (19)0.19989 (18)0.41200 (17)0.0614 (4)
C140.70825 (16)0.09209 (15)0.51729 (14)0.0536 (4)
C150.76728 (18)−0.04619 (16)0.51217 (16)0.0608 (4)
C160.83062 (18)−0.15070 (16)0.61020 (16)0.0613 (4)
C170.83684 (18)−0.11806 (15)0.71615 (16)0.0577 (4)
C180.7792 (2)0.01956 (16)0.72397 (16)0.0651 (5)
C190.71601 (18)0.12164 (16)0.62642 (15)0.0609 (5)
C200.9415 (3)−0.35674 (17)0.82635 (19)0.0885 (6)
H10.58980.65840.05760.0816*
H20.48350.8080−0.11790.0897*
H30.18680.8676−0.09740.0847*
H5−0.12520.85390.04350.0870*
H6−0.31720.77320.24260.0938*
H7−0.21230.63120.42110.0865*
H80.08430.56690.39970.0718*
H150.7639−0.06890.44030.0730*
H160.8687−0.24230.60440.0735*
H180.78370.04190.79570.0781*
H190.67740.21290.63310.0730*
H20A0.8377−0.39920.82830.1062*
H20B1.0349−0.36190.75210.1062*
H20C0.9808−0.40860.90370.1062*
H130.649 (2)0.1693 (17)0.3375 (17)0.079 (5)*
H120.5628 (18)0.3682 (16)0.4790 (16)0.068 (5)*
H110.5287 (18)0.3968 (15)0.2201 (15)0.066 (5)*
U11U22U33U12U13U23
O10.1091 (9)0.0578 (7)0.0842 (9)0.0041 (6)−0.0426 (7)−0.0244 (7)
N10.0581 (7)0.0672 (8)0.0580 (8)0.0028 (6)−0.0176 (6)−0.0249 (7)
C10.0576 (9)0.0868 (12)0.0616 (11)−0.0092 (8)−0.0069 (8)−0.0310 (9)
C20.0780 (12)0.0922 (13)0.0484 (10)−0.0202 (9)−0.0031 (9)−0.0199 (10)
C30.0879 (12)0.0742 (11)0.0495 (10)−0.0087 (9)−0.0203 (9)−0.0161 (8)
C40.0674 (10)0.0550 (9)0.0543 (9)−0.0044 (7)−0.0197 (8)−0.0227 (8)
C50.0743 (11)0.0790 (12)0.0742 (12)0.0069 (9)−0.0337 (10)−0.0295 (10)
C60.0582 (10)0.1012 (14)0.0835 (14)0.0039 (9)−0.0213 (10)−0.0409 (12)
C70.0567 (10)0.0882 (12)0.0686 (12)−0.0073 (8)−0.0049 (9)−0.0293 (10)
C80.0614 (9)0.0612 (10)0.0548 (10)−0.0055 (7)−0.0115 (8)−0.0180 (8)
C90.0563 (8)0.0464 (8)0.0489 (9)−0.0057 (6)−0.0129 (7)−0.0197 (7)
C100.0570 (9)0.0594 (9)0.0524 (9)−0.0044 (7)−0.0138 (7)−0.0268 (8)
C110.0543 (9)0.0688 (10)0.0611 (10)−0.0011 (7)−0.0127 (8)−0.0289 (9)
C120.0508 (8)0.0699 (11)0.0643 (11)0.0021 (7)−0.0156 (8)−0.0305 (9)
C130.0560 (9)0.0712 (11)0.0645 (11)−0.0021 (7)−0.0151 (8)−0.0319 (9)
C140.0466 (8)0.0581 (9)0.0621 (10)−0.0033 (6)−0.0117 (7)−0.0283 (8)
C150.0606 (9)0.0666 (10)0.0675 (11)−0.0029 (7)−0.0163 (8)−0.0365 (9)
C160.0629 (9)0.0546 (9)0.0753 (11)−0.0013 (7)−0.0174 (8)−0.0328 (9)
C170.0581 (9)0.0538 (9)0.0645 (10)−0.0058 (7)−0.0176 (8)−0.0206 (8)
C180.0795 (11)0.0617 (10)0.0659 (11)0.0001 (8)−0.0235 (9)−0.0325 (9)
C190.0635 (9)0.0582 (9)0.0705 (11)0.0037 (7)−0.0189 (8)−0.0336 (9)
C200.1086 (14)0.0560 (11)0.0975 (15)0.0034 (9)−0.0321 (12)−0.0192 (10)
O1—C171.367 (2)C16—C171.370 (3)
O1—C201.415 (2)C17—C181.394 (3)
N1—C101.415 (2)C18—C191.367 (3)
N1—C111.275 (2)C1—H10.930
C1—C21.399 (3)C2—H20.930
C1—C101.3723 (19)C3—H30.930
C2—C31.356 (3)C5—H50.930
C3—C41.413 (2)C6—H60.930
C4—C51.416 (3)C7—H70.930
C4—C91.417 (2)C8—H80.930
C5—C61.358 (3)C11—H110.996 (19)
C6—C71.393 (3)C12—H120.99 (2)
C7—C81.360 (2)C13—H130.98 (2)
C8—C91.4129 (18)C15—H150.930
C9—C101.4313 (19)C16—H160.930
C11—C121.440 (3)C18—H180.930
C12—C131.337 (3)C19—H190.930
C13—C141.454 (3)C20—H20A0.960
C14—C151.393 (3)C20—H20B0.960
C14—C191.393 (3)C20—H20C0.960
C15—C161.380 (3)
O1···C193.5931 (18)C16···H2vi3.4384
N1···C82.8446 (19)C17···H2vi2.9036
N1···C133.591 (2)C17···H15v3.5517
C1···C42.795 (2)C18···H2vi3.0680
C1···C112.973 (2)C18···H15v3.5526
C2···C92.7901 (19)C19···H6viii3.2467
C3···C102.802 (3)C19···H8iii3.5445
C4···C72.793 (2)C20···H1vi3.2542
C5···C82.771 (3)C20···H3i3.5996
C6···C92.792 (2)C20···H20Cxiv3.2874
C9···C113.432 (2)H1···O1ix3.1078
C12···C193.021 (3)H1···C5vii3.3934
C14···C172.793 (2)H1···C6vii3.3460
C15···C182.740 (3)H1···C20ix3.2542
C16···C192.762 (3)H1···H5vii3.1004
C16···C202.847 (3)H1···H6vii3.0108
O1···C3i3.575 (3)H1···H20Aix2.9604
O1···C5i3.436 (3)H1···H20Cix3.1705
C3···O1ii3.575 (3)H2···O1ix3.1163
C5···O1ii3.436 (3)H2···C11x3.5870
C9···C18iii3.529 (3)H2···C16ix3.4384
C9···C20iv3.514 (3)H2···C17ix2.9036
C13···C15iv3.514 (3)H2···C18ix3.0680
C14···C16v3.5413 (19)H2···H18ix3.2497
C15···C13iv3.514 (3)H2···H20Aix3.2383
C16···C14v3.5413 (19)H2···H13x2.8988
C18···C9iii3.529 (3)H2···H11x2.6953
C20···C9iv3.514 (3)H3···O1ii2.9743
O1···H162.6497H3···C5xi3.2551
O1···H182.4698H3···C6xi3.5624
N1···H12.6251H3···C20ii3.5996
N1···H82.5217H3···H5xi2.9716
N1···H122.605 (16)H3···H6xi3.5192
C1···H33.2362H3···H20Cii3.3696
C1···H112.799 (13)H3···H13x2.8004
C3···H13.2290H3···H11x3.5828
C3···H52.6593H5···O1ii2.7982
C4···H23.2415H5···C3xi3.2536
C4···H63.2532H5···C4xi3.5955
C4···H83.2748H5···H1xii3.1004
C5···H32.6625H5···H3xi2.9716
C5···H73.2219H5···H5xi3.4288
C6···H83.2269H5···H18ii2.9949
C7···H53.2253H5···H20Cii3.3902
C8···H63.2234H6···N1xii3.0857
C9···H13.2629H6···C1xii3.3336
C9···H33.2803H6···C10xii3.3944
C9···H53.2749H6···C19viii3.2467
C9···H73.2508H6···H1xii3.0108
C10···H23.2399H6···H3xi3.5192
C10···H82.6639H6···H15xiii3.3938
C10···H112.474 (14)H6···H19viii2.7811
C11···H12.8555H6···H12viii3.1520
C11···H83.4223H7···N1viii3.1177
C11···H132.573 (16)H7···C8viii3.5163
C12···H192.7411H7···C11viii3.2841
C13···H152.6229H7···C12viii3.0068
C13···H192.6553H7···H8viii2.5990
C13···H112.637 (15)H7···H15xiii3.0266
C14···H163.2628H7···H16xiii3.0273
C14···H183.2431H7···H12xii3.1315
C14···H122.731 (15)H7···H12viii2.6565
C15···H193.2194H8···C7viii3.1161
C15···H132.608 (16)H8···C8viii2.9850
C16···H183.2298H8···C19iii3.5445
C16···H20A2.8179H8···H7viii2.5990
C16···H20B2.7583H8···H8viii2.3227
C17···H153.2076H8···H16xiii3.4321
C17···H193.2288H8···H16iv3.1918
C17···H20A2.6182H8···H19iii2.9362
C17···H20B2.6321H8···H20Aiv3.4229
C17···H20C3.1856H8···H20Biv3.4544
C18···H163.2356H15···C6xv3.3733
C19···H153.2172H15···C7xv3.1604
C19···H133.34 (2)H15···C13iv3.3659
C19···H122.753 (14)H15···C17v3.5517
C20···H162.5691H15···C18v3.5526
H1···H22.3150H15···H6xv3.3938
H1···H112.6153H15···H7xv3.0266
H2···H32.2748H15···H13iv3.5238
H3···H52.5070H16···C7xv3.4602
H5···H62.2784H16···C8iv3.5808
H6···H72.3162H16···C11iv3.3910
H7···H82.2802H16···C14v3.5385
H15···H162.2998H16···H7xv3.0273
H15···H132.3948H16···H8xv3.4321
H16···H20A2.4372H16···H8iv3.1918
H16···H20B2.3010H16···H11iv3.4288
H16···H20C3.5218H18···C3iii3.4003
H18···H192.2854H18···C4iii2.9952
H19···H122.1952H18···C5iii3.5603
H13···H122.86 (3)H18···C8iii3.4145
H13···H112.39 (2)H18···C9iii2.9091
H12···H112.95 (3)H18···C10iii3.2988
O1···H1vi3.1078H18···H2vi3.2497
O1···H2vi3.1163H18···H5i2.9949
O1···H3i2.9743H19···N1iii2.6991
O1···H5i2.7982H19···C8iii3.1087
O1···H13v3.492 (14)H19···C9iii3.0520
N1···H6vii3.0857H19···C10iii2.8908
N1···H7viii3.1177H19···H6viii2.7811
N1···H19iii2.6991H19···H8iii2.9362
N1···H20Aiv3.4788H20A···N1iv3.4788
N1···H12iii2.99 (2)H20A···C1vi3.5932
C1···H6vii3.3336H20A···C4iv3.3507
C1···H20Aix3.5932H20A···C8iv3.1971
C2···H13x3.40 (2)H20A···C9iv2.8631
C2···H11x3.002 (19)H20A···C10iv3.0175
C3···H5xi3.2536H20A···C11iv3.4725
C3···H18iii3.4003H20A···H1vi2.9604
C3···H20Cii3.5201H20A···H2vi3.2383
C3···H13x3.350 (19)H20A···H8iv3.4229
C3···H11x3.518 (17)H20A···H20Cxiv3.5351
C4···H5xi3.5955H20A···H11iv3.0661
C4···H18iii2.9952H20B···C7iv3.4084
C4···H20Aiv3.3507H20B···C8iv3.2280
C4···H20Cii3.5750H20B···C9iv3.4819
C5···H1xii3.3934H20B···C11v3.4783
C5···H3xi3.2551H20B···C12v3.0819
C5···H18iii3.5603H20B···C13v2.9736
C5···H20Cii3.5450H20B···C14v3.5936
C6···H1xii3.3460H20B···H8iv3.4544
C6···H3xi3.5624H20B···H13v3.0639
C6···H15xiii3.3733H20B···H12v3.4957
C7···H8viii3.1161H20B···H11v3.4741
C7···H15xiii3.1604H20C···C3i3.5201
C7···H16xiii3.4602H20C···C4i3.5750
C7···H20Biv3.4084H20C···C5i3.5450
C7···H12viii3.407 (13)H20C···C20xiv3.2874
C8···H7viii3.5163H20C···H1vi3.1705
C8···H8viii2.9850H20C···H3i3.3696
C8···H16iv3.5808H20C···H5i3.3902
C8···H18iii3.4145H20C···H20Axiv3.5351
C8···H19iii3.1087H20C···H20Cxiv2.3622
C8···H20Aiv3.1971H13···O1v3.492 (14)
C8···H20Biv3.2280H13···C2x3.40 (2)
C9···H18iii2.9091H13···C3x3.350 (19)
C9···H19iii3.0520H13···C15iv3.408 (15)
C9···H20Aiv2.8631H13···H2x2.8988
C9···H20Biv3.4819H13···H3x2.8004
C10···H6vii3.3944H13···H15iv3.5238
C10···H18iii3.2988H13···H20Bv3.0639
C10···H19iii2.8908H12···N1iii2.99 (2)
C10···H20Aiv3.0175H12···C7viii3.407 (13)
C11···H2x3.5870H12···C12iii3.546 (18)
C11···H7viii3.2841H12···H6viii3.1520
C11···H16iv3.3910H12···H7vii3.1315
C11···H20Aiv3.4725H12···H7viii2.6565
C11···H20Bv3.4783H12···H20Bv3.4957
C12···H7viii3.0068H12···H12iii2.80 (3)
C12···H20Bv3.0819H11···C2x3.002 (19)
C12···H12iii3.546 (18)H11···C3x3.518 (17)
C13···H15iv3.3659H11···H2x2.6953
C13···H20Bv2.9736H11···H3x3.5828
C14···H16v3.5385H11···H16iv3.4288
C14···H20Bv3.5936H11···H20Aiv3.0661
C15···H13iv3.408 (15)H11···H20Bv3.4741
C17—O1—C20118.68 (17)C1—C2—H2119.427
C10—N1—C11118.58 (16)C3—C2—H2119.432
C2—C1—C10120.77 (14)C2—C3—H3119.786
C1—C2—C3121.14 (14)C4—C3—H3119.786
C2—C3—C4120.43 (16)C4—C5—H5119.513
C3—C4—C5122.40 (15)C6—C5—H5119.515
C3—C4—C9119.11 (14)C5—C6—H6119.772
C5—C4—C9118.48 (13)C7—C6—H6119.774
C4—C5—C6120.97 (16)C6—C7—H7119.763
C5—C6—C7120.45 (15)C8—C7—H7119.761
C6—C7—C8120.48 (14)C7—C8—H8119.545
C7—C8—C9120.91 (15)C9—C8—H8119.541
C4—C9—C8118.70 (13)N1—C11—H11119.7 (8)
C4—C9—C10119.14 (12)C12—C11—H11117.7 (8)
C8—C9—C10122.16 (13)C11—C12—H12118.1 (8)
N1—C10—C1122.72 (13)C13—C12—H12119.4 (8)
N1—C10—C9117.83 (11)C12—C13—H13116.7 (9)
C1—C10—C9119.36 (14)C14—C13—H13115.5 (9)
N1—C11—C12122.63 (18)C14—C15—H15118.908
C11—C12—C13122.4 (2)C16—C15—H15118.902
C12—C13—C14127.9 (2)C15—C16—H16120.344
C13—C14—C15120.78 (17)C17—C16—H16120.341
C13—C14—C19122.17 (15)C17—C18—H18119.941
C15—C14—C19117.05 (14)C19—C18—H18119.932
C14—C15—C16122.19 (18)C14—C19—H19119.279
C15—C16—C17119.31 (16)C18—C19—H19119.265
O1—C17—C16125.37 (14)O1—C20—H20A109.474
O1—C17—C18114.76 (17)O1—C20—H20B109.470
C16—C17—C18119.87 (15)O1—C20—H20C109.474
C17—C18—C19120.13 (19)H20A—C20—H20B109.465
C14—C19—C18121.46 (16)H20A—C20—H20C109.473
C2—C1—H1119.613H20B—C20—H20C109.471
C10—C1—H1119.613
C20—O1—C17—C16−7.9 (2)C7—C8—C9—C4−0.0 (3)
C20—O1—C17—C18173.05 (12)C7—C8—C9—C10−179.05 (16)
C10—N1—C11—C12179.54 (12)C4—C9—C10—N1179.14 (14)
C11—N1—C10—C1−57.2 (2)C4—C9—C10—C12.4 (3)
C11—N1—C10—C9126.13 (15)C8—C9—C10—N1−1.8 (3)
C2—C1—C10—N1−177.42 (17)C8—C9—C10—C1−178.62 (15)
C2—C1—C10—C9−0.8 (3)N1—C11—C12—C13168.88 (13)
C10—C1—C2—C3−1.0 (3)C11—C12—C13—C14−176.86 (12)
C1—C2—C3—C41.2 (3)C12—C13—C14—C15175.95 (13)
C2—C3—C4—C5179.28 (17)C12—C13—C14—C19−4.6 (3)
C2—C3—C4—C90.4 (3)C13—C14—C15—C16179.68 (11)
C3—C4—C5—C6−178.93 (17)C13—C14—C19—C18−179.34 (11)
C3—C4—C9—C8178.80 (15)C15—C14—C19—C180.17 (18)
C3—C4—C9—C10−2.1 (3)C19—C14—C15—C160.16 (18)
C5—C4—C9—C8−0.1 (3)C14—C15—C16—C17−0.3 (2)
C5—C4—C9—C10178.92 (15)C15—C16—C17—O1−178.93 (12)
C9—C4—C5—C6−0.0 (3)C15—C16—C17—C180.10 (19)
C4—C5—C6—C70.4 (4)O1—C17—C18—C19179.35 (11)
C5—C6—C7—C8−0.5 (4)C16—C17—C18—C190.2 (2)
C6—C7—C8—C90.3 (3)C17—C18—C19—C14−0.4 (2)
  4 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.  1,2-Dicarba-closo-dodecaboran-1-yl naphthalene derivatives.

Authors:  Kiminori Ohta; Tokuhito Goto; Yasuyuki Endo
Journal:  Inorg Chem       Date:  2005-11-14       Impact factor: 5.165

3.  (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

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

Authors:  Jae Kyun Lee; Kee Dal Nam; Joo Hwan Cha; Yong Seo Cho; Joon Kyun Lee
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-06-08
  4 in total

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