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The title compound, C30H23N, was synthesized via the Ullmann reaction. The plane of the vinyl linkage almost coincides with the plane of the directly attached aromatic ring of the triarylamine group [dihedral angle 6.2 (2)°] and forms a dihedral angle of 41.07 (4)° with the mean plane of the naphthalene group.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025200/ya6182sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025200/ya6182Isup2.hkl
Contains datablock I

CCDC reference: 227917

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.044
  • wR factor = 0.121
  • Data-to-parameter ratio = 13.5

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.874 0.990 Tmin' and Tmax expected: 0.984 0.989 RR' = 0.887 Please check that your absorption correction is appropriate. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 = 5.24 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C24 - C25 = 5.09 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

4-[2-(1-Naphthyl)vinyl]-N,N-diphenylaniline top
Crystal data top
C30H23NF(000) = 420
Mr = 397.49Dx = 1.222 Mg m3
Triclinic, P1Melting point: 413 K
a = 8.883 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.446 (3) ÅCell parameters from 1023 reflections
c = 13.466 (4) Åθ = 2.4–26.3°
α = 88.416 (5)°µ = 0.07 mm1
β = 83.527 (4)°T = 293 K
γ = 74.129 (4)°Block, yellow
V = 1079.9 (6) Å30.22 × 0.20 × 0.16 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer
3781 independent reflections
Radiation source: fine-focus sealed tube2384 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 810
Tmin = 0.874, Tmax = 0.990k = 811
5593 measured reflectionsl = 1415
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.0514P)2 + 0.1151P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.121(Δ/σ)max = 0.003
S = 1.00Δρmax = 0.12 e Å3
3781 reflectionsΔρmin = 0.14 e Å3
280 parameters
Special details top

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*/Ueq
C10.3037 (2)0.7995 (2)0.11437 (14)0.0577 (5)
C20.4182 (3)0.8385 (2)0.05084 (16)0.0719 (6)
H20.46100.91180.06990.086*
C30.4699 (3)0.7710 (3)0.0398 (2)0.0965 (9)
H30.54670.79950.08200.116*
C40.4110 (5)0.6639 (4)0.0688 (2)0.1120 (12)
H40.44810.61770.13030.134*
C50.2968 (4)0.6232 (3)0.0077 (3)0.1067 (10)
H50.25600.54920.02780.128*
C60.2408 (3)0.6919 (3)0.08458 (19)0.0815 (7)
H60.16170.66510.12560.098*
C70.2192 (2)1.0239 (2)0.21585 (14)0.0557 (5)
C80.2768 (3)1.0867 (2)0.28879 (16)0.0700 (6)
H80.33751.02700.33380.084*
C90.2456 (3)1.2366 (3)0.29571 (17)0.0803 (7)
H90.28461.27730.34590.096*
C100.1587 (3)1.3266 (3)0.23055 (19)0.0830 (7)
H100.13811.42820.23600.100*
C110.1015 (3)1.2663 (3)0.15680 (18)0.0806 (7)
H110.04291.32720.11140.097*
C120.1305 (2)1.1150 (2)0.14936 (15)0.0675 (6)
H120.09011.07470.09960.081*
C130.2384 (2)0.7833 (2)0.29496 (14)0.0547 (5)
C140.3516 (2)0.6521 (2)0.30818 (14)0.0598 (5)
H140.43740.62130.26000.072*
C150.3388 (2)0.5669 (2)0.39149 (14)0.0574 (5)
H150.41640.47960.39870.069*
C160.2118 (2)0.6087 (2)0.46532 (14)0.0515 (5)
C170.1007 (2)0.7411 (2)0.45134 (15)0.0595 (5)
H170.01520.77250.49960.071*
C180.1128 (2)0.8277 (2)0.36844 (14)0.0599 (5)
H180.03660.91620.36180.072*
C190.1929 (2)0.5201 (2)0.55406 (14)0.0563 (5)
H190.10940.56250.60160.068*
C200.2794 (2)0.3876 (2)0.57545 (14)0.0542 (5)
H200.36200.34230.52820.065*
C210.2559 (2)0.3059 (2)0.66751 (14)0.0521 (5)
C220.2151 (2)0.3766 (2)0.75810 (15)0.0664 (6)
H220.20380.47730.76090.080*
C230.1900 (3)0.3009 (3)0.84651 (16)0.0796 (7)
H230.16240.35180.90690.096*
C240.2056 (3)0.1546 (3)0.84486 (16)0.0757 (7)
H240.18880.10560.90420.091*
C250.2469 (2)0.0756 (2)0.75431 (14)0.0586 (5)
C260.2582 (3)0.0764 (3)0.75003 (19)0.0760 (7)
H260.23920.12620.80860.091*
C270.2961 (3)0.1507 (3)0.6624 (2)0.0798 (7)
H270.30350.25080.66120.096*
C280.3238 (2)0.0778 (2)0.57440 (18)0.0719 (6)
H280.35000.12940.51420.086*
C290.3128 (2)0.0685 (2)0.57543 (15)0.0598 (5)
H290.33130.11550.51550.072*
C300.2743 (2)0.1509 (2)0.66471 (14)0.0500 (5)
N10.2510 (2)0.86917 (18)0.20842 (12)0.0651 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0648 (13)0.0538 (12)0.0561 (12)0.0171 (10)0.0117 (10)0.0034 (10)
C20.0767 (15)0.0730 (15)0.0647 (14)0.0221 (12)0.0008 (11)0.0023 (12)
C30.108 (2)0.087 (2)0.0729 (17)0.0019 (16)0.0133 (14)0.0007 (15)
C40.165 (3)0.078 (2)0.0662 (18)0.018 (2)0.023 (2)0.0049 (16)
C50.155 (3)0.0676 (18)0.105 (2)0.0200 (18)0.066 (2)0.0115 (17)
C60.0935 (18)0.0707 (16)0.0902 (18)0.0321 (13)0.0277 (14)0.0026 (14)
C70.0604 (12)0.0546 (12)0.0520 (11)0.0201 (10)0.0044 (9)0.0069 (10)
C80.0908 (16)0.0585 (14)0.0659 (14)0.0271 (12)0.0156 (12)0.0100 (11)
C90.114 (2)0.0615 (16)0.0717 (15)0.0352 (14)0.0067 (14)0.0015 (12)
C100.1030 (19)0.0519 (14)0.0839 (17)0.0158 (13)0.0194 (14)0.0011 (13)
C110.0797 (16)0.0685 (16)0.0766 (16)0.0012 (12)0.0047 (13)0.0211 (13)
C120.0694 (14)0.0717 (16)0.0597 (13)0.0179 (11)0.0044 (10)0.0061 (11)
C130.0634 (13)0.0500 (12)0.0555 (11)0.0249 (10)0.0039 (10)0.0063 (9)
C140.0586 (12)0.0556 (13)0.0640 (12)0.0192 (10)0.0069 (10)0.0018 (10)
C150.0547 (12)0.0468 (12)0.0696 (13)0.0147 (9)0.0024 (10)0.0066 (10)
C160.0494 (11)0.0480 (11)0.0600 (11)0.0194 (9)0.0045 (9)0.0065 (9)
C170.0495 (11)0.0602 (13)0.0658 (12)0.0154 (10)0.0042 (9)0.0100 (10)
C180.0530 (12)0.0530 (12)0.0711 (13)0.0133 (9)0.0018 (10)0.0125 (10)
C190.0542 (12)0.0551 (12)0.0612 (12)0.0203 (10)0.0007 (9)0.0061 (10)
C200.0555 (11)0.0523 (12)0.0566 (11)0.0188 (9)0.0035 (9)0.0045 (10)
C210.0474 (11)0.0572 (12)0.0536 (11)0.0167 (9)0.0087 (8)0.0069 (10)
C220.0714 (14)0.0680 (14)0.0626 (13)0.0238 (11)0.0074 (11)0.0004 (11)
C230.0905 (17)0.099 (2)0.0520 (13)0.0316 (15)0.0054 (11)0.0022 (13)
C240.0819 (16)0.0930 (19)0.0558 (13)0.0303 (13)0.0123 (11)0.0229 (13)
C250.0519 (12)0.0682 (14)0.0571 (12)0.0172 (10)0.0135 (9)0.0175 (11)
C260.0729 (15)0.0703 (16)0.0857 (17)0.0208 (12)0.0173 (12)0.0341 (14)
C270.0824 (16)0.0548 (14)0.1027 (19)0.0199 (12)0.0128 (14)0.0153 (14)
C280.0716 (14)0.0580 (14)0.0843 (16)0.0168 (11)0.0022 (11)0.0009 (12)
C290.0582 (12)0.0581 (13)0.0619 (12)0.0166 (10)0.0020 (9)0.0081 (10)
C300.0410 (10)0.0565 (12)0.0535 (11)0.0141 (8)0.0100 (8)0.0110 (9)
N10.0947 (13)0.0501 (10)0.0535 (10)0.0298 (9)0.0042 (9)0.0046 (8)
Geometric parameters (Å, º) top
C1—C61.375 (3)C15—C161.393 (2)
C1—C21.376 (3)C15—H150.9300
C1—N11.414 (2)C16—C171.389 (2)
C2—C31.366 (3)C16—C191.460 (2)
C2—H20.9300C17—C181.377 (3)
C3—C41.344 (4)C17—H170.9300
C3—H30.9300C18—H180.9300
C4—C51.365 (4)C19—C201.320 (3)
C4—H40.9300C19—H190.9300
C5—C61.393 (4)C20—C211.468 (2)
C5—H50.9300C20—H200.9300
C6—H60.9300C21—C221.371 (3)
C7—C81.375 (3)C21—C301.429 (3)
C7—C121.382 (3)C22—C231.399 (3)
C7—N11.415 (2)C22—H220.9300
C8—C91.370 (3)C23—C241.352 (3)
C8—H80.9300C23—H230.9300
C9—C101.357 (3)C24—C251.406 (3)
C9—H90.9300C24—H240.9300
C10—C111.368 (3)C25—C261.414 (3)
C10—H100.9300C25—C301.415 (3)
C11—C121.385 (3)C26—C271.351 (3)
C11—H110.9300C26—H260.9300
C12—H120.9300C27—C281.386 (3)
C13—C181.385 (3)C27—H270.9300
C13—C141.387 (3)C28—C291.360 (3)
C13—N11.413 (2)C28—H280.9300
C14—C151.375 (3)C29—C301.407 (3)
C14—H140.9300C29—H290.9300
C6—C1—C2118.8 (2)C15—C16—C19122.93 (18)
C6—C1—N1120.5 (2)C18—C17—C16122.32 (18)
C2—C1—N1120.70 (19)C18—C17—H17118.8
C3—C2—C1120.8 (2)C16—C17—H17118.8
C3—C2—H2119.6C17—C18—C13120.08 (19)
C1—C2—H2119.6C17—C18—H18120.0
C4—C3—C2120.8 (3)C13—C18—H18120.0
C4—C3—H3119.6C20—C19—C16128.28 (19)
C2—C3—H3119.6C20—C19—H19115.9
C3—C4—C5119.8 (3)C16—C19—H19115.9
C3—C4—H4120.1C19—C20—C21125.47 (18)
C5—C4—H4120.1C19—C20—H20117.3
C4—C5—C6120.5 (3)C21—C20—H20117.3
C4—C5—H5119.8C22—C21—C30118.49 (18)
C6—C5—H5119.8C22—C21—C20120.73 (18)
C1—C6—C5119.3 (3)C30—C21—C20120.78 (17)
C1—C6—H6120.3C21—C22—C23121.6 (2)
C5—C6—H6120.3C21—C22—H22119.2
C8—C7—C12118.6 (2)C23—C22—H22119.2
C8—C7—N1120.78 (19)C24—C23—C22120.6 (2)
C12—C7—N1120.58 (19)C24—C23—H23119.7
C9—C8—C7120.5 (2)C22—C23—H23119.7
C9—C8—H8119.7C23—C24—C25120.6 (2)
C7—C8—H8119.7C23—C24—H24119.7
C10—C9—C8121.1 (2)C25—C24—H24119.7
C10—C9—H9119.4C24—C25—C26121.8 (2)
C8—C9—H9119.4C24—C25—C30119.2 (2)
C9—C10—C11119.3 (2)C26—C25—C30119.0 (2)
C9—C10—H10120.4C27—C26—C25121.2 (2)
C11—C10—H10120.4C27—C26—H26119.4
C10—C11—C12120.4 (2)C25—C26—H26119.4
C10—C11—H11119.8C26—C27—C28120.0 (2)
C12—C11—H11119.8C26—C27—H27120.0
C7—C12—C11120.0 (2)C28—C27—H27120.0
C7—C12—H12120.0C29—C28—C27120.4 (2)
C11—C12—H12120.0C29—C28—H28119.8
C18—C13—C14118.43 (18)C27—C28—H28119.8
C18—C13—N1120.87 (18)C28—C29—C30121.8 (2)
C14—C13—N1120.70 (18)C28—C29—H29119.1
C15—C14—C13120.99 (18)C30—C29—H29119.1
C15—C14—H14119.5C29—C30—C25117.49 (19)
C13—C14—H14119.5C29—C30—C21122.95 (17)
C14—C15—C16121.34 (18)C25—C30—C21119.51 (18)
C14—C15—H15119.3C13—N1—C1119.80 (16)
C16—C15—H15119.3C13—N1—C7120.46 (16)
C17—C16—C15116.82 (17)C1—N1—C7119.65 (16)
C17—C16—C19120.25 (17)
C6—C1—C2—C30.6 (3)C20—C21—C22—C23179.08 (19)
N1—C1—C2—C3179.70 (19)C21—C22—C23—C240.0 (3)
C1—C2—C3—C40.6 (4)C22—C23—C24—C250.1 (3)
C2—C3—C4—C50.9 (4)C23—C24—C25—C26177.6 (2)
C3—C4—C5—C60.1 (4)C23—C24—C25—C300.9 (3)
C2—C1—C6—C51.4 (3)C24—C25—C26—C27179.2 (2)
N1—C1—C6—C5178.91 (19)C30—C25—C26—C270.7 (3)
C4—C5—C6—C11.1 (4)C25—C26—C27—C280.4 (3)
C12—C7—C8—C90.5 (3)C26—C27—C28—C290.1 (3)
N1—C7—C8—C9179.93 (19)C27—C28—C29—C300.3 (3)
C7—C8—C9—C100.6 (3)C28—C29—C30—C250.0 (3)
C8—C9—C10—C110.0 (4)C28—C29—C30—C21177.45 (18)
C9—C10—C11—C120.8 (3)C24—C25—C30—C29178.97 (17)
C8—C7—C12—C110.2 (3)C26—C25—C30—C290.5 (3)
N1—C7—C12—C11179.35 (18)C24—C25—C30—C211.5 (3)
C10—C11—C12—C70.9 (3)C26—C25—C30—C21177.05 (17)
C18—C13—C14—C150.9 (3)C22—C21—C30—C29178.70 (17)
N1—C13—C14—C15179.02 (18)C20—C21—C30—C291.0 (3)
C13—C14—C15—C160.2 (3)C22—C21—C30—C251.3 (3)
C14—C15—C16—C170.9 (3)C20—C21—C30—C25178.36 (16)
C14—C15—C16—C19179.05 (17)C18—C13—N1—C1140.1 (2)
C15—C16—C17—C180.6 (3)C14—C13—N1—C139.8 (3)
C19—C16—C17—C18179.41 (18)C18—C13—N1—C743.2 (3)
C16—C17—C18—C130.5 (3)C14—C13—N1—C7136.9 (2)
C14—C13—C18—C171.2 (3)C6—C1—N1—C1347.9 (3)
N1—C13—C18—C17178.68 (17)C2—C1—N1—C13132.4 (2)
C17—C16—C19—C20174.2 (2)C6—C1—N1—C7135.4 (2)
C15—C16—C19—C205.8 (3)C2—C1—N1—C744.3 (3)
C16—C19—C20—C21178.50 (17)C8—C7—N1—C1344.3 (3)
C19—C20—C21—C2239.4 (3)C12—C7—N1—C13136.2 (2)
C19—C20—C21—C30140.3 (2)C8—C7—N1—C1132.4 (2)
C30—C21—C22—C230.6 (3)C12—C7—N1—C147.2 (3)
 

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