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The highly conjugated title compound, (E)-N-{(5-[(E)-1-naphthyl­imino­meth­yl]-2-thienylmethyl­ene}naphthalen-1-amine dichloro­methane hemisolvate, C26H18N2S·0.5CH2Cl2, exhibits a non-planar yet extended configuration. The naphthyl ring systems are twisted 33.8 (4) and 32.6 (5)° out of the mean plane that passes through the thio­phene ring. The nitro­gen-containing double bonds are ca 0.05 Å shorter than their carbon analogues and both adopt the thermodynamically favourable E configuration.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005411/sj6193sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005411/sj6193Isup2.hkl
Contains datablock I

CCDC reference: 601251

Key indicators

  • Single-crystal X-ray study
  • T = 220 K
  • Mean [sigma](C-C) = 0.008 Å
  • Disorder in solvent or counterion
  • R factor = 0.065
  • wR factor = 0.166
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT431_ALERT_2_B Short Inter HL..A Contact Cl1 .. Cl2 .. 3.02 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.76 mm PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C31 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.03
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 72.85 From the CIF: _reflns_number_total 4127 Count of symmetry unique reflns 2416 Completeness (_total/calc) 170.82% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1711 Fraction of Friedel pairs measured 0.708 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program).

(E)—N-{(5-[(E)-1-naphthyliminomethyl]-2-thienylmethylene}naphthalen-1-amine dichloromethane hemisolvate top
Crystal data top
C26H18N2S·0.5CH2Cl2F(000) = 450
Mr = 432.97Dx = 1.304 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ybCell parameters from 3232 reflections
a = 11.2320 (8) Åθ = 2.7–72.1°
b = 5.8762 (2) ŵ = 2.53 mm1
c = 16.7657 (9) ÅT = 220 K
β = 94.872 (4)°Needle, yellow–orange
V = 1102.56 (11) Å30.76 × 0.09 × 0.05 mm
Z = 2
Data collection top
Bruker SMART 2K/PLATFORM
diffractometer
4127 independent reflections
Radiation source: Sealed Tube2223 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 5.5 pixels mm-1θmax = 72.9°, θmin = 2.6°
ω scansh = 1310
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
k = 77
Tmin = 0.417, Tmax = 0.883l = 2020
9046 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.065 w = 1/[σ2(Fo2) + (0.0811P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.166(Δ/σ)max < 0.001
S = 0.87Δρmax = 0.27 e Å3
4127 reflectionsΔρmin = 0.25 e Å3
290 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
25 restraintsExtinction coefficient: 0.0022 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1741 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.00 (3)
Special details top

Experimental. X-ray crystallographic data for (1) were collected from a single-crystal sample, which was mounted on a loop fiber. Data were collected using a Bruker Platform diffractometer, equipped with a Bruker SMART 2 K Charged-Coupled Device (CCD) Area Detector using the program SMART and normal focus sealed tube source graphite monochromated Cu—Kα radiation. The crystal-to-detector distance was 4.908 cm, and the data collection was carried out in 512 x 512 pixel mode, utilizing 4 x 4 pixel binning. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 9.0 degree scan in 30 frames over four different parts of the reciprocal space (120 frames total). One complete sphere of data was collected, to better than 0.8 Å resolution. Upon completion of the data collection, the first 101 frames were recollected in order to improve the decay correction analysis.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.32408 (12)0.48586 (19)0.98036 (7)0.0587 (4)
N10.2676 (4)0.4222 (6)0.8000 (2)0.0574 (11)
N20.3741 (4)0.4300 (6)1.1610 (2)0.0554 (11)
C10.2888 (5)0.6260 (8)0.8230 (3)0.0581 (14)
H10.28530.74160.78410.070*
C20.3179 (4)0.6887 (9)0.9052 (3)0.0570 (13)
C30.3418 (5)0.8989 (8)0.9351 (3)0.0607 (13)
H30.34251.03010.90300.073*
C40.3655 (5)0.9022 (8)1.0185 (3)0.0604 (14)
H40.38291.03581.04800.072*
C50.3607 (4)0.6912 (8)1.0525 (3)0.0535 (12)
C60.3801 (5)0.6338 (8)1.1345 (3)0.0600 (14)
H60.39850.75131.17150.072*
C70.2419 (5)0.3814 (8)0.7175 (3)0.0556 (13)
C80.2947 (5)0.4961 (11)0.6602 (3)0.0723 (14)
H80.34980.61180.67530.087*
C90.2692 (5)0.4467 (11)0.5792 (3)0.0776 (17)
H90.30540.53130.54030.093*
C100.1902 (5)0.2719 (11)0.5561 (3)0.0768 (18)
H100.17350.23740.50160.092*
C110.1361 (5)0.1489 (9)0.6135 (3)0.0636 (15)
C120.0575 (5)0.0365 (12)0.5915 (3)0.0824 (17)
H120.04230.07660.53730.099*
C130.0049 (6)0.1547 (12)0.6485 (4)0.092 (2)
H130.04730.27520.63330.110*
C140.0269 (5)0.1000 (10)0.7293 (4)0.0825 (19)
H140.01080.18250.76800.099*
C150.1029 (5)0.0722 (8)0.7521 (3)0.0682 (16)
H150.11780.10700.80680.082*
C160.1593 (5)0.1982 (9)0.6958 (3)0.0568 (13)
C170.4005 (5)0.3875 (8)1.2435 (3)0.0542 (13)
C180.4852 (5)0.5103 (9)1.2900 (3)0.0680 (15)
H180.52730.62801.26700.082*
C190.5085 (5)0.4597 (11)1.3717 (3)0.0778 (17)
H190.56530.54611.40310.093*
C200.4505 (6)0.2885 (11)1.4061 (3)0.0775 (18)
H200.46720.25761.46090.093*
C210.3645 (5)0.1551 (9)1.3598 (3)0.0647 (15)
C220.3055 (6)0.0328 (12)1.3943 (3)0.0783 (16)
H220.32420.07091.44830.094*
C230.2236 (6)0.1546 (10)1.3495 (4)0.088 (2)
H230.18520.27751.37240.106*
C240.1948 (6)0.0996 (10)1.2686 (4)0.0799 (18)
H240.13620.18421.23810.096*
C250.2512 (5)0.0760 (9)1.2336 (3)0.0668 (16)
H250.23210.10911.17920.080*
C260.3382 (5)0.2083 (8)1.2788 (3)0.0535 (12)
C310.0066 (18)0.155 (5)1.0040 (16)0.120 (6)0.50
H31A0.08740.15881.03110.144*0.50
H31B0.04930.17231.04550.144*0.50
Cl10.0140 (15)0.092 (6)0.9650 (14)0.435 (10)0.50
Cl20.0095 (14)0.399 (7)0.9407 (10)0.503 (18)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0854 (9)0.0317 (5)0.0581 (7)0.0012 (7)0.0003 (6)0.0008 (7)
N10.074 (3)0.045 (2)0.054 (2)0.003 (2)0.007 (2)0.0012 (18)
N20.072 (3)0.043 (3)0.051 (2)0.0002 (19)0.007 (2)0.0011 (18)
C10.080 (4)0.040 (3)0.055 (3)0.002 (2)0.007 (3)0.012 (2)
C20.068 (4)0.049 (3)0.053 (3)0.009 (3)0.001 (2)0.001 (2)
C30.088 (4)0.038 (2)0.057 (3)0.003 (3)0.010 (3)0.003 (2)
C40.080 (4)0.033 (2)0.067 (3)0.006 (2)0.001 (3)0.009 (2)
C50.066 (3)0.041 (3)0.053 (3)0.001 (2)0.000 (2)0.004 (2)
C60.082 (4)0.041 (3)0.057 (3)0.000 (3)0.009 (3)0.006 (3)
C70.073 (4)0.049 (3)0.045 (3)0.013 (3)0.006 (2)0.005 (2)
C80.100 (4)0.063 (3)0.055 (3)0.002 (4)0.014 (3)0.005 (3)
C90.089 (4)0.084 (5)0.063 (3)0.003 (4)0.024 (3)0.005 (3)
C100.093 (5)0.095 (5)0.042 (3)0.023 (4)0.003 (3)0.002 (3)
C110.074 (4)0.063 (3)0.052 (3)0.013 (3)0.001 (3)0.006 (3)
C120.094 (5)0.082 (5)0.067 (4)0.000 (4)0.016 (3)0.010 (4)
C130.098 (5)0.074 (4)0.098 (5)0.014 (4)0.027 (4)0.007 (4)
C140.083 (5)0.070 (4)0.091 (5)0.015 (3)0.010 (3)0.009 (3)
C150.081 (4)0.055 (3)0.066 (4)0.003 (3)0.006 (3)0.000 (3)
C160.065 (4)0.047 (3)0.059 (3)0.014 (2)0.005 (3)0.004 (2)
C170.073 (4)0.046 (3)0.044 (3)0.006 (3)0.004 (2)0.005 (2)
C180.100 (4)0.041 (3)0.060 (3)0.003 (3)0.008 (3)0.008 (3)
C190.099 (5)0.073 (4)0.057 (3)0.007 (4)0.016 (3)0.008 (3)
C200.096 (5)0.082 (4)0.054 (4)0.024 (4)0.004 (3)0.002 (3)
C210.082 (4)0.063 (3)0.050 (3)0.021 (3)0.014 (3)0.000 (3)
C220.115 (5)0.068 (4)0.054 (3)0.015 (4)0.022 (3)0.004 (4)
C230.119 (6)0.055 (4)0.096 (5)0.004 (4)0.041 (4)0.013 (4)
C240.094 (5)0.061 (3)0.087 (4)0.013 (3)0.019 (4)0.013 (3)
C250.089 (5)0.057 (3)0.055 (3)0.001 (3)0.011 (3)0.000 (3)
C260.074 (4)0.038 (2)0.049 (3)0.007 (2)0.012 (3)0.003 (2)
C310.074 (8)0.146 (11)0.141 (10)0.012 (8)0.019 (7)0.008 (9)
Cl10.288 (13)0.55 (3)0.50 (2)0.067 (19)0.204 (15)0.01 (3)
Cl20.283 (12)0.84 (6)0.374 (17)0.03 (2)0.014 (13)0.10 (3)
Geometric parameters (Å, º) top
S1—C21.732 (5)C13—H130.94
S1—C51.734 (5)C14—C151.358 (7)
N1—C11.274 (6)C14—H140.94
N1—C71.409 (6)C15—C161.393 (7)
N2—C61.281 (6)C15—H150.94
N2—C171.413 (6)C17—C181.381 (6)
C1—C21.436 (6)C17—C261.421 (7)
C1—H10.94C18—C191.404 (6)
C2—C31.351 (6)C18—H180.94
C3—C41.401 (6)C19—C201.353 (8)
C3—H30.94C19—H190.94
C4—C51.368 (6)C20—C211.423 (7)
C4—H40.94C20—H200.94
C5—C61.414 (7)C21—C261.400 (6)
C6—H60.94C21—C221.434 (8)
C7—C81.351 (6)C22—C231.344 (8)
C7—C161.448 (7)C22—H220.94
C8—C91.394 (6)C23—C241.406 (7)
C8—H80.94C23—H230.94
C9—C101.391 (8)C24—C251.368 (7)
C9—H90.94C24—H240.94
C10—C111.385 (7)C25—C261.417 (7)
C10—H100.94C25—H250.94
C11—C161.412 (6)C31—Cl11.603 (19)
C11—C121.430 (8)C31—Cl21.78 (4)
C12—C131.357 (8)C31—H31a0.98
C12—H120.94C31—H31b0.98
C13—C141.394 (7)
C2—S1—C591.2 (2)C13—C14—H14119.9
C1—N1—C7118.3 (4)C14—C15—C16121.1 (6)
C6—N2—C17119.5 (4)C14—C15—H15119.5
N1—C1—C2123.6 (5)C16—C15—H15119.5
N1—C1—H1118.2C15—C16—C11119.7 (5)
C2—C1—H1118.2C15—C16—C7122.9 (5)
C3—C2—C1127.7 (5)C11—C16—C7117.4 (5)
C3—C2—S1111.4 (4)C18—C17—N2122.5 (5)
C1—C2—S1120.9 (4)C18—C17—C26119.4 (5)
C2—C3—C4113.4 (4)N2—C17—C26118.0 (4)
C2—C3—H3123.3C17—C18—C19120.2 (6)
C4—C3—H3123.3C17—C18—H18119.9
C5—C4—C3113.1 (4)C19—C18—H18119.9
C5—C4—H4123.4C20—C19—C18121.1 (6)
C3—C4—H4123.4C20—C19—H19119.5
C4—C5—C6127.9 (5)C18—C19—H19119.5
C4—C5—S1110.8 (4)C19—C20—C21120.4 (5)
C6—C5—S1121.3 (4)C19—C20—H20119.8
N2—C6—C5123.5 (5)C21—C20—H20119.8
N2—C6—H6118.3C26—C21—C20119.0 (5)
C5—C6—H6118.3C26—C21—C22119.7 (5)
C8—C7—N1123.2 (5)C20—C21—C22121.3 (5)
C8—C7—C16120.2 (5)C23—C22—C21120.2 (5)
N1—C7—C16116.6 (4)C23—C22—H22119.9
C7—C8—C9121.5 (6)C21—C22—H22119.9
C7—C8—H8119.2C22—C23—C24120.5 (6)
C9—C8—H8119.2C22—C23—H23119.7
C10—C9—C8119.9 (6)C24—C23—H23119.7
C10—C9—H9120.1C25—C24—C23120.6 (6)
C8—C9—H9120.1C25—C24—H24119.7
C11—C10—C9120.0 (5)C23—C24—H24119.7
C11—C10—H10120C24—C25—C26120.6 (5)
C9—C10—H10120C24—C25—H25119.7
C10—C11—C16121.1 (5)C26—C25—H25119.7
C10—C11—C12121.1 (5)C21—C26—C25118.4 (5)
C16—C11—C12117.8 (5)C21—C26—C17119.9 (5)
C13—C12—C11120.3 (5)C25—C26—C17121.7 (5)
C13—C12—H12119.8CL1—C31—CL2119 (2)
C11—C12—H12119.8CL1—C31—H31A107.6
C12—C13—C14120.9 (6)CL2—C31—H31A107.6
C12—C13—H13119.5CL1—C31—H31B107.6
C14—C13—H13119.5CL2—C31—H31B107.6
C15—C14—C13120.1 (6)H31A—C31—H31B107
C15—C14—H14119.9
C7—N1—C1—C2179.0 (4)C12—C11—C16—C152.1 (7)
N1—C1—C2—C3179.9 (6)C10—C11—C16—C70.2 (7)
N1—C1—C2—S10.9 (8)C12—C11—C16—C7178.1 (5)
C5—S1—C2—C30.4 (5)C8—C7—C16—C15179.3 (5)
C5—S1—C2—C1179.7 (4)N1—C7—C16—C152.6 (7)
C1—C2—C3—C4179.2 (5)C8—C7—C16—C110.8 (7)
S1—C2—C3—C40.0 (6)N1—C7—C16—C11177.5 (4)
C2—C3—C4—C50.6 (7)C6—N2—C17—C1833.6 (7)
C3—C4—C5—C6179.8 (5)C6—N2—C17—C26147.5 (5)
C3—C4—C5—S10.9 (6)N2—C17—C18—C19179.5 (5)
C2—S1—C5—C40.7 (4)C26—C17—C18—C190.7 (8)
C2—S1—C5—C6179.9 (4)C17—C18—C19—C201.1 (9)
C17—N2—C6—C5177.1 (4)C18—C19—C20—C210.2 (9)
C4—C5—C6—N2179.7 (6)C19—C20—C21—C262.0 (8)
S1—C5—C6—N21.0 (8)C19—C20—C21—C22177.5 (5)
C1—N1—C7—C836.1 (7)C26—C21—C22—C231.3 (8)
C1—N1—C7—C16147.3 (5)C20—C21—C22—C23179.2 (5)
N1—C7—C8—C9178.3 (5)C21—C22—C23—C240.0 (9)
C16—C7—C8—C91.8 (8)C22—C23—C24—C251.2 (9)
C7—C8—C9—C101.7 (9)C23—C24—C25—C261.2 (8)
C8—C9—C10—C110.6 (8)C20—C21—C26—C25179.2 (5)
C9—C10—C11—C160.3 (8)C22—C21—C26—C251.4 (7)
C9—C10—C11—C12177.9 (5)C20—C21—C26—C172.4 (7)
C10—C11—C12—C13179.7 (6)C22—C21—C26—C17177.1 (5)
C16—C11—C12—C132.0 (8)C24—C25—C26—C210.1 (7)
C11—C12—C13—C140.7 (9)C24—C25—C26—C17178.2 (5)
C12—C13—C14—C150.6 (9)C18—C17—C26—C211.1 (7)
C13—C14—C15—C160.5 (8)N2—C17—C26—C21177.8 (4)
C14—C15—C16—C110.9 (8)C18—C17—C26—C25179.5 (5)
C14—C15—C16—C7179.3 (5)N2—C17—C26—C250.6 (7)
C10—C11—C16—C15179.6 (5)
 

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