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The title compound, C32H27N, was synthesized via the Ullmann reaction. The structure has a pseudo-twofold axis approximately parallel to the b axis, and hence the pseudo-space group C2/c. The crystal packing is stabilized by weak C—H...π and and van der Waals interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025285/ci6291sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025285/ci6291Isup2.hkl
Contains datablock I

CCDC reference: 227881

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.056
  • wR factor = 0.154
  • Data-to-parameter ratio = 7.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 81 PerFit PLAT113_ALERT_2_B ADDSYM Suggests Possible Pseudo/New Spacegroup . C2/c
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.10 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.96 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
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 25.00 From the CIF: _reflns_number_total 2130 Count of symmetry unique reflns 2131 Completeness (_total/calc) 99.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 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-[(1-Naphthyl)vinyl]phenyl}di-p-tolylamine top
Crystal data top
C32H27NF(000) = 904
Mr = 425.55Dx = 1.167 Mg m3
Monoclinic, CcMelting point = 383–386 K
Hall symbol: C -2ycMo Kα radiation, λ = 0.71073 Å
a = 18.482 (7) ÅCell parameters from 724 reflections
b = 17.045 (7) Åθ = 2.4–21.7°
c = 8.635 (3) ŵ = 0.07 mm1
β = 117.094 (5)°T = 293 K
V = 2421.9 (16) Å3Plate, yellow
Z = 40.40 × 0.34 × 0.28 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2130 independent reflections
Radiation source: fine-focus sealed tube1453 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 2121
Tmin = 0.973, Tmax = 0.981k = 2010
5052 measured reflectionsl = 107
Refinement top
Refinement on F274 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.0877P)2 + 0.2832P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.154(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.18 e Å3
2130 reflectionsΔρmin = 0.17 e Å3
300 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
N10.1212 (3)0.18419 (18)0.4176 (7)0.0544 (9)
C10.1941 (3)0.1443 (3)0.4472 (6)0.0491 (12)
C20.2680 (3)0.1696 (3)0.5739 (7)0.0623 (14)
H20.27080.21200.64430.075*
C30.3376 (3)0.1319 (4)0.5954 (8)0.0720 (16)
H30.38730.15000.68070.086*
C40.3367 (3)0.0693 (3)0.4971 (8)0.0643 (15)
C50.2617 (3)0.0437 (3)0.3715 (7)0.0646 (15)
H50.25880.00060.30270.078*
C60.1911 (3)0.0811 (3)0.3471 (7)0.0570 (13)
H60.14130.06330.26200.068*
C70.4135 (4)0.0291 (5)0.5208 (11)0.101 (2)
H7A0.45430.06780.53830.152*
H7B0.40290.00120.41900.152*
H7C0.43250.00480.62030.152*
C80.0517 (3)0.1396 (3)0.3910 (7)0.0517 (13)
C90.0576 (3)0.0757 (4)0.4948 (8)0.0739 (17)
H90.10790.06210.58490.089*
C100.0097 (4)0.0320 (4)0.4670 (9)0.0780 (17)
H100.00390.01060.53880.094*
C110.0845 (3)0.0496 (3)0.3367 (7)0.0608 (14)
C120.0916 (3)0.1139 (4)0.2354 (7)0.0658 (15)
H120.14250.12800.14830.079*
C130.0241 (3)0.1584 (3)0.2602 (7)0.0592 (14)
H130.03020.20110.18820.071*
C140.1582 (4)0.0004 (4)0.3066 (9)0.090 (2)
H14A0.20650.02570.22210.135*
H14B0.16140.00520.41400.135*
H14C0.15340.05050.26450.135*
C150.1190 (3)0.2659 (2)0.4240 (7)0.0477 (10)
C160.0721 (3)0.3039 (3)0.4874 (7)0.0539 (13)
H160.04160.27440.52700.065*
C170.0694 (3)0.3846 (3)0.4937 (7)0.0595 (13)
H170.03640.40810.53540.071*
C180.1148 (3)0.4313 (3)0.4393 (7)0.0540 (12)
C190.1629 (3)0.3932 (3)0.3758 (6)0.0554 (13)
H190.19430.42270.33860.066*
C200.1642 (3)0.3126 (3)0.3677 (6)0.0530 (13)
H200.19620.28870.32350.064*
C210.1092 (3)0.5166 (3)0.4529 (7)0.0614 (13)
H210.07390.53450.49480.074*
C220.1483 (3)0.5707 (3)0.4125 (7)0.0672 (15)
H220.18460.55400.37210.081*
C230.1394 (4)0.6557 (3)0.4263 (8)0.0688 (18)
C240.0682 (5)0.6879 (4)0.4052 (9)0.092 (2)
H240.02470.65480.38450.111*
C250.0578 (7)0.7689 (6)0.4132 (11)0.114 (3)
H250.00820.78880.39800.137*
C260.1182 (9)0.8166 (5)0.4421 (13)0.118 (3)
H260.11020.87030.44520.141*
C270.1936 (7)0.7895 (4)0.4682 (10)0.100 (2)
C280.2058 (5)0.7066 (3)0.4607 (8)0.0794 (18)
C290.2826 (5)0.6806 (4)0.4872 (9)0.094 (2)
H290.28990.62710.47860.112*
C300.3481 (6)0.7299 (5)0.5254 (11)0.127 (3)
H300.39810.71070.54150.152*
C310.3353 (7)0.8110 (6)0.5387 (13)0.140 (3)
H310.37820.84580.56790.168*
C320.2614 (8)0.8386 (5)0.5097 (12)0.125 (3)
H320.25520.89240.51750.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0410 (18)0.0349 (18)0.087 (3)0.000 (2)0.0293 (17)0.001 (2)
C10.042 (3)0.043 (3)0.060 (3)0.002 (2)0.020 (3)0.003 (2)
C20.054 (3)0.055 (3)0.072 (4)0.000 (3)0.024 (3)0.010 (3)
C30.044 (3)0.067 (4)0.085 (4)0.001 (3)0.012 (3)0.001 (3)
C40.050 (3)0.065 (4)0.082 (4)0.014 (3)0.034 (3)0.013 (3)
C50.063 (4)0.056 (3)0.076 (4)0.011 (3)0.033 (3)0.000 (3)
C60.046 (3)0.044 (3)0.070 (3)0.005 (2)0.017 (3)0.006 (2)
C70.068 (4)0.105 (5)0.136 (6)0.025 (4)0.051 (4)0.006 (4)
C80.047 (3)0.040 (3)0.073 (4)0.001 (2)0.031 (3)0.000 (3)
C90.044 (3)0.075 (4)0.091 (4)0.001 (3)0.021 (3)0.024 (3)
C100.064 (4)0.068 (4)0.096 (4)0.004 (3)0.031 (3)0.022 (3)
C110.054 (3)0.063 (3)0.068 (4)0.010 (3)0.030 (3)0.008 (3)
C120.045 (3)0.078 (4)0.064 (3)0.002 (3)0.016 (3)0.012 (3)
C130.054 (3)0.056 (3)0.064 (4)0.006 (3)0.023 (3)0.005 (2)
C140.068 (4)0.097 (5)0.107 (5)0.030 (4)0.041 (4)0.019 (4)
C150.042 (2)0.042 (2)0.058 (2)0.000 (2)0.0220 (19)0.001 (3)
C160.059 (3)0.047 (3)0.065 (3)0.001 (2)0.036 (3)0.001 (2)
C170.061 (3)0.055 (3)0.066 (3)0.006 (3)0.032 (3)0.002 (3)
C180.044 (3)0.045 (3)0.059 (3)0.002 (3)0.011 (2)0.006 (2)
C190.051 (3)0.048 (3)0.063 (3)0.007 (2)0.022 (3)0.013 (3)
C200.049 (3)0.053 (3)0.061 (3)0.001 (2)0.029 (3)0.002 (2)
C210.052 (3)0.062 (3)0.069 (3)0.003 (3)0.026 (2)0.002 (3)
C220.077 (4)0.056 (3)0.064 (3)0.000 (3)0.029 (3)0.002 (3)
C230.107 (6)0.043 (3)0.055 (3)0.015 (3)0.035 (3)0.000 (3)
C240.133 (6)0.058 (4)0.087 (5)0.023 (4)0.051 (4)0.006 (3)
C250.146 (7)0.103 (6)0.097 (5)0.038 (5)0.059 (5)0.001 (4)
C260.174 (7)0.073 (4)0.101 (5)0.013 (6)0.058 (5)0.002 (4)
C270.159 (6)0.069 (4)0.075 (4)0.024 (5)0.057 (4)0.004 (4)
C280.140 (6)0.046 (3)0.056 (3)0.007 (4)0.047 (4)0.003 (3)
C290.119 (6)0.072 (4)0.091 (5)0.019 (4)0.049 (4)0.009 (4)
C300.166 (7)0.105 (5)0.110 (5)0.046 (5)0.064 (5)0.016 (4)
C310.177 (7)0.114 (6)0.125 (6)0.061 (6)0.064 (6)0.015 (5)
C320.193 (8)0.074 (4)0.103 (5)0.027 (5)0.063 (5)0.012 (4)
Geometric parameters (Å, º) top
N1—C151.395 (5)C15—C201.393 (7)
N1—C81.417 (6)C16—C171.377 (7)
N1—C11.425 (6)C16—H160.93
C1—C61.367 (7)C17—C181.384 (7)
C1—C21.374 (7)C17—H170.93
C2—C31.373 (8)C18—C191.398 (7)
C2—H20.93C18—C211.467 (7)
C3—C41.360 (8)C19—C201.377 (7)
C3—H30.93C19—H190.93
C4—C51.386 (8)C20—H200.93
C4—C71.503 (8)C21—C221.314 (7)
C5—C61.378 (7)C21—H210.93
C5—H50.93C22—C231.469 (7)
C6—H60.93C22—H220.93
C7—H7A0.96C23—C241.358 (9)
C7—H7B0.96C23—C281.419 (9)
C7—H7C0.96C24—C251.401 (11)
C8—C131.378 (7)C24—H240.93
C8—C91.384 (8)C25—C261.309 (13)
C9—C101.374 (8)C25—H250.93
C9—H90.93C26—C271.386 (14)
C10—C111.361 (8)C26—H260.93
C10—H100.93C27—C321.412 (13)
C11—C121.370 (8)C27—C281.435 (9)
C11—C141.518 (7)C28—C291.403 (10)
C12—C131.391 (7)C29—C301.385 (10)
C12—H120.93C29—H290.93
C13—H130.93C30—C311.415 (13)
C14—H14A0.96C30—H300.93
C14—H14B0.96C31—C321.355 (12)
C14—H14C0.96C31—H310.93
C15—C161.379 (7)C32—H320.93
C15—N1—C8120.1 (4)C20—C15—N1121.5 (4)
C15—N1—C1120.8 (4)C17—C16—C15121.7 (5)
C8—N1—C1119.1 (3)C17—C16—H16119.1
C6—C1—C2119.4 (5)C15—C16—H16119.1
C6—C1—N1120.0 (5)C16—C17—C18121.4 (5)
C2—C1—N1120.6 (4)C16—C17—H17119.3
C3—C2—C1119.4 (5)C18—C17—H17119.3
C3—C2—H2120.3C17—C18—C19117.2 (4)
C1—C2—H2120.3C17—C18—C21117.9 (5)
C4—C3—C2122.6 (6)C19—C18—C21124.9 (4)
C4—C3—H3118.7C20—C19—C18120.9 (4)
C2—C3—H3118.7C20—C19—H19119.6
C3—C4—C5117.3 (5)C18—C19—H19119.6
C3—C4—C7122.0 (6)C19—C20—C15121.6 (4)
C5—C4—C7120.7 (6)C19—C20—H20119.2
C6—C5—C4120.9 (5)C15—C20—H20119.2
C6—C5—H5119.5C22—C21—C18127.4 (5)
C4—C5—H5119.5C22—C21—H21116.3
C1—C6—C5120.3 (5)C18—C21—H21116.3
C1—C6—H6119.8C21—C22—C23125.1 (5)
C5—C6—H6119.8C21—C22—H22117.5
C4—C7—H7A109.5C23—C22—H22117.5
C4—C7—H7B109.5C24—C23—C28118.3 (6)
H7A—C7—H7B109.5C24—C23—C22121.7 (6)
C4—C7—H7C109.5C28—C23—C22120.1 (6)
H7A—C7—H7C109.5C23—C24—C25122.5 (8)
H7B—C7—H7C109.5C23—C24—H24118.8
C13—C8—C9117.6 (5)C25—C24—H24118.8
C13—C8—N1121.1 (5)C26—C25—C24119.8 (9)
C9—C8—N1121.3 (5)C26—C25—H25120.1
C10—C9—C8121.1 (5)C24—C25—H25120.1
C10—C9—H9119.5C25—C26—C27122.0 (8)
C8—C9—H9119.5C25—C26—H26119.0
C11—C10—C9121.6 (6)C27—C26—H26119.0
C11—C10—H10119.2C26—C27—C32123.7 (9)
C9—C10—H10119.2C26—C27—C28119.1 (8)
C10—C11—C12118.0 (5)C32—C27—C28117.1 (9)
C10—C11—C14121.0 (6)C29—C28—C23123.7 (5)
C12—C11—C14121.0 (6)C29—C28—C27118.1 (7)
C11—C12—C13121.3 (5)C23—C28—C27118.2 (7)
C11—C12—H12119.3C30—C29—C28123.9 (7)
C13—C12—H12119.3C30—C29—H29118.1
C8—C13—C12120.4 (5)C28—C29—H29118.1
C8—C13—H13119.8C29—C30—C31116.8 (9)
C12—C13—H13119.8C29—C30—H30121.6
C11—C14—H14A109.5C31—C30—H30121.6
C11—C14—H14B109.5C32—C31—C30121.1 (9)
H14A—C14—H14B109.5C32—C31—H31119.4
C11—C14—H14C109.5C30—C31—H31119.4
H14A—C14—H14C109.5C31—C32—C27122.9 (9)
H14B—C14—H14C109.5C31—C32—H32118.5
C16—C15—C20117.2 (4)C27—C32—H32118.5
C16—C15—N1121.3 (5)
C15—N1—C1—C6139.1 (5)C15—C16—C17—C181.2 (8)
C8—N1—C1—C644.4 (7)C16—C17—C18—C190.7 (8)
C15—N1—C1—C239.7 (8)C16—C17—C18—C21179.1 (5)
C8—N1—C1—C2136.9 (5)C17—C18—C19—C200.3 (8)
C6—C1—C2—C31.1 (8)C21—C18—C19—C20179.9 (5)
N1—C1—C2—C3177.6 (5)C18—C19—C20—C150.8 (8)
C1—C2—C3—C40.7 (9)C16—C15—C20—C190.4 (8)
C2—C3—C4—C50.2 (9)N1—C15—C20—C19179.2 (5)
C2—C3—C4—C7179.3 (6)C17—C18—C21—C22178.3 (6)
C3—C4—C5—C60.6 (8)C19—C18—C21—C221.5 (10)
C7—C4—C5—C6178.8 (6)C18—C21—C22—C23179.0 (5)
C2—C1—C6—C50.7 (8)C21—C22—C23—C2430.6 (10)
N1—C1—C6—C5178.1 (5)C21—C22—C23—C28150.1 (5)
C4—C5—C6—C10.2 (8)C28—C23—C24—C251.1 (10)
C15—N1—C8—C1348.1 (7)C22—C23—C24—C25178.3 (6)
C1—N1—C8—C13135.4 (5)C23—C24—C25—C260.0 (12)
C15—N1—C8—C9132.1 (6)C24—C25—C26—C271.0 (14)
C1—N1—C8—C944.5 (8)C25—C26—C27—C32176.2 (7)
C13—C8—C9—C100.8 (9)C25—C26—C27—C280.9 (13)
N1—C8—C9—C10179.1 (6)C24—C23—C28—C29179.2 (6)
C8—C9—C10—C110.0 (10)C22—C23—C28—C291.5 (9)
C9—C10—C11—C121.5 (9)C24—C23—C28—C271.1 (8)
C9—C10—C11—C14179.5 (6)C22—C23—C28—C27178.2 (5)
C10—C11—C12—C132.2 (8)C26—C27—C28—C29179.9 (8)
C14—C11—C12—C13178.8 (5)C32—C27—C28—C292.8 (9)
C9—C8—C13—C120.1 (7)C26—C27—C28—C230.2 (9)
N1—C8—C13—C12179.8 (5)C32—C27—C28—C23177.5 (7)
C11—C12—C13—C81.4 (8)C23—C28—C29—C30178.2 (6)
C8—N1—C15—C1631.6 (8)C27—C28—C29—C302.1 (10)
C1—N1—C15—C16144.9 (5)C28—C29—C30—C310.4 (11)
C8—N1—C15—C20148.8 (5)C29—C30—C31—C322.1 (13)
C1—N1—C15—C2034.7 (8)C30—C31—C32—C271.2 (14)
C20—C15—C16—C170.6 (9)C26—C27—C32—C31178.4 (9)
N1—C15—C16—C17179.8 (5)C28—C27—C32—C311.3 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···Cg3i0.933.093.835 (7)138
C10—H10···Cg1ii0.933.264.107 (8)153
C16—H16···Cg2i0.933.153.586 (6)111
C20—H20···Cg2iii0.933.033.592 (6)121
C30—H30···Cg1iv0.933.304.079 (11)142
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y, z+1/2; (iii) x, y+1, z1/2; (iv) x+1/2, y+1/2, z.
 

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