4-[2-(1-Naphthyl)­vinyl]-N,N-di­phenyl­aniline

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.

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

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Computing details

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

Crystal data

C30H23N	F(000) = 420
Mr = 397.49	Dx = 1.222 Mg m^−3
Triclinic, P1	Melting point: 413 K
a = 8.883 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.446 (3) Å	Cell parameters from 1023 reflections
c = 13.466 (4) Å	θ = 2.4–26.3°
α = 88.416 (5)°	µ = 0.07 mm^−1
β = 83.527 (4)°	T = 293 K
γ = 74.129 (4)°	Block, yellow
V = 1079.9 (6) Å^3	0.22 × 0.20 × 0.16 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3781 independent reflections
Radiation source: fine-focus sealed tube	2384 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −8→10
Tmin = 0.874, Tmax = 0.990	k = −8→11
5593 measured reflections	l = −14→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0514P)^2 + 0.1151P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.121	(Δ/σ)max = 0.003
S = 1.00	Δρmax = 0.12 e Å^−3
3781 reflections	Δρmin = −0.14 e Å^−3
280 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3037 (2)	0.7995 (2)	0.11437 (14)	0.0577 (5)
C2	0.4182 (3)	0.8385 (2)	0.05084 (16)	0.0719 (6)
H2	0.4610	0.9118	0.0699	0.086*
C3	0.4699 (3)	0.7710 (3)	−0.0398 (2)	0.0965 (9)
H3	0.5467	0.7995	−0.0820	0.116*
C4	0.4110 (5)	0.6639 (4)	−0.0688 (2)	0.1120 (12)
H4	0.4481	0.6177	−0.1303	0.134*
C5	0.2968 (4)	0.6232 (3)	−0.0077 (3)	0.1067 (10)
H5	0.2560	0.5492	−0.0278	0.128*
C6	0.2408 (3)	0.6919 (3)	0.08458 (19)	0.0815 (7)
H6	0.1617	0.6651	0.1256	0.098*
C7	0.2192 (2)	1.0239 (2)	0.21585 (14)	0.0557 (5)
C8	0.2768 (3)	1.0867 (2)	0.28879 (16)	0.0700 (6)
H8	0.3375	1.0270	0.3338	0.084*
C9	0.2456 (3)	1.2366 (3)	0.29571 (17)	0.0803 (7)
H9	0.2846	1.2773	0.3459	0.096*
C10	0.1587 (3)	1.3266 (3)	0.23055 (19)	0.0830 (7)
H10	0.1381	1.4282	0.2360	0.100*
C11	0.1015 (3)	1.2663 (3)	0.15680 (18)	0.0806 (7)
H11	0.0429	1.3272	0.1114	0.097*
C12	0.1305 (2)	1.1150 (2)	0.14936 (15)	0.0675 (6)
H12	0.0901	1.0747	0.0996	0.081*
C13	0.2384 (2)	0.7833 (2)	0.29496 (14)	0.0547 (5)
C14	0.3516 (2)	0.6521 (2)	0.30818 (14)	0.0598 (5)
H14	0.4374	0.6213	0.2600	0.072*
C15	0.3388 (2)	0.5669 (2)	0.39149 (14)	0.0574 (5)
H15	0.4164	0.4796	0.3987	0.069*
C16	0.2118 (2)	0.6087 (2)	0.46532 (14)	0.0515 (5)
C17	0.1007 (2)	0.7411 (2)	0.45134 (15)	0.0595 (5)
H17	0.0152	0.7725	0.4996	0.071*
C18	0.1128 (2)	0.8277 (2)	0.36844 (14)	0.0599 (5)
H18	0.0366	0.9162	0.3618	0.072*
C19	0.1929 (2)	0.5201 (2)	0.55406 (14)	0.0563 (5)
H19	0.1094	0.5625	0.6016	0.068*
C20	0.2794 (2)	0.3876 (2)	0.57545 (14)	0.0542 (5)
H20	0.3620	0.3423	0.5282	0.065*
C21	0.2559 (2)	0.3059 (2)	0.66751 (14)	0.0521 (5)
C22	0.2151 (2)	0.3766 (2)	0.75810 (15)	0.0664 (6)
H22	0.2038	0.4773	0.7609	0.080*
C23	0.1900 (3)	0.3009 (3)	0.84651 (16)	0.0796 (7)
H23	0.1624	0.3518	0.9069	0.096*
C24	0.2056 (3)	0.1546 (3)	0.84486 (16)	0.0757 (7)
H24	0.1888	0.1056	0.9042	0.091*
C25	0.2469 (2)	0.0756 (2)	0.75431 (14)	0.0586 (5)
C26	0.2582 (3)	−0.0764 (3)	0.75003 (19)	0.0760 (7)
H26	0.2392	−0.1262	0.8086	0.091*
C27	0.2961 (3)	−0.1507 (3)	0.6624 (2)	0.0798 (7)
H27	0.3035	−0.2508	0.6612	0.096*
C28	0.3238 (2)	−0.0778 (2)	0.57440 (18)	0.0719 (6)
H28	0.3500	−0.1294	0.5142	0.086*
C29	0.3128 (2)	0.0685 (2)	0.57543 (15)	0.0598 (5)
H29	0.3313	0.1155	0.5155	0.072*
C30	0.2743 (2)	0.1509 (2)	0.66471 (14)	0.0500 (5)
N1	0.2510 (2)	0.86917 (18)	0.20842 (12)	0.0651 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0648 (13)	0.0538 (12)	0.0561 (12)	−0.0171 (10)	−0.0117 (10)	0.0034 (10)
C2	0.0767 (15)	0.0730 (15)	0.0647 (14)	−0.0221 (12)	0.0008 (11)	0.0023 (12)
C3	0.108 (2)	0.087 (2)	0.0729 (17)	0.0019 (16)	0.0133 (14)	−0.0007 (15)
C4	0.165 (3)	0.078 (2)	0.0662 (18)	0.018 (2)	−0.023 (2)	−0.0049 (16)
C5	0.155 (3)	0.0676 (18)	0.105 (2)	−0.0200 (18)	−0.066 (2)	−0.0115 (17)
C6	0.0935 (18)	0.0707 (16)	0.0902 (18)	−0.0321 (13)	−0.0277 (14)	0.0026 (14)
C7	0.0604 (12)	0.0546 (12)	0.0520 (11)	−0.0201 (10)	0.0044 (9)	0.0069 (10)
C8	0.0908 (16)	0.0585 (14)	0.0659 (14)	−0.0271 (12)	−0.0156 (12)	0.0100 (11)
C9	0.114 (2)	0.0615 (16)	0.0717 (15)	−0.0352 (14)	−0.0067 (14)	0.0015 (12)
C10	0.1030 (19)	0.0519 (14)	0.0839 (17)	−0.0158 (13)	0.0194 (14)	0.0011 (13)
C11	0.0797 (16)	0.0685 (16)	0.0766 (16)	0.0012 (12)	0.0047 (13)	0.0211 (13)
C12	0.0694 (14)	0.0717 (16)	0.0597 (13)	−0.0179 (11)	−0.0044 (10)	0.0061 (11)
C13	0.0634 (13)	0.0500 (12)	0.0555 (11)	−0.0249 (10)	−0.0039 (10)	0.0063 (9)
C14	0.0586 (12)	0.0556 (13)	0.0640 (12)	−0.0192 (10)	0.0069 (10)	0.0018 (10)
C15	0.0547 (12)	0.0468 (12)	0.0696 (13)	−0.0147 (9)	−0.0024 (10)	0.0066 (10)
C16	0.0494 (11)	0.0480 (11)	0.0600 (11)	−0.0194 (9)	−0.0045 (9)	0.0065 (9)
C17	0.0495 (11)	0.0602 (13)	0.0658 (12)	−0.0154 (10)	0.0042 (9)	0.0100 (10)
C18	0.0530 (12)	0.0530 (12)	0.0711 (13)	−0.0133 (9)	−0.0018 (10)	0.0125 (10)
C19	0.0542 (12)	0.0551 (12)	0.0612 (12)	−0.0203 (10)	−0.0007 (9)	0.0061 (10)
C20	0.0555 (11)	0.0523 (12)	0.0566 (11)	−0.0188 (9)	−0.0035 (9)	0.0045 (10)
C21	0.0474 (11)	0.0572 (12)	0.0536 (11)	−0.0167 (9)	−0.0087 (8)	0.0069 (10)
C22	0.0714 (14)	0.0680 (14)	0.0626 (13)	−0.0238 (11)	−0.0074 (11)	−0.0004 (11)
C23	0.0905 (17)	0.099 (2)	0.0520 (13)	−0.0316 (15)	−0.0054 (11)	−0.0022 (13)
C24	0.0819 (16)	0.0930 (19)	0.0558 (13)	−0.0303 (13)	−0.0123 (11)	0.0229 (13)
C25	0.0519 (12)	0.0682 (14)	0.0571 (12)	−0.0172 (10)	−0.0135 (9)	0.0175 (11)
C26	0.0729 (15)	0.0703 (16)	0.0857 (17)	−0.0208 (12)	−0.0173 (12)	0.0341 (14)
C27	0.0824 (16)	0.0548 (14)	0.1027 (19)	−0.0199 (12)	−0.0128 (14)	0.0153 (14)
C28	0.0716 (14)	0.0580 (14)	0.0843 (16)	−0.0168 (11)	−0.0022 (11)	−0.0009 (12)
C29	0.0582 (12)	0.0581 (13)	0.0619 (12)	−0.0166 (10)	−0.0020 (9)	0.0081 (10)
C30	0.0410 (10)	0.0565 (12)	0.0535 (11)	−0.0141 (8)	−0.0100 (8)	0.0110 (9)
N1	0.0947 (13)	0.0501 (10)	0.0535 (10)	−0.0298 (9)	0.0042 (9)	0.0046 (8)

Geometric parameters (Å, º)

C1—C6	1.375 (3)	C15—C16	1.393 (2)
C1—C2	1.376 (3)	C15—H15	0.9300
C1—N1	1.414 (2)	C16—C17	1.389 (2)
C2—C3	1.366 (3)	C16—C19	1.460 (2)
C2—H2	0.9300	C17—C18	1.377 (3)
C3—C4	1.344 (4)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.365 (4)	C19—C20	1.320 (3)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.393 (4)	C20—C21	1.468 (2)
C5—H5	0.9300	C20—H20	0.9300
C6—H6	0.9300	C21—C22	1.371 (3)
C7—C8	1.375 (3)	C21—C30	1.429 (3)
C7—C12	1.382 (3)	C22—C23	1.399 (3)
C7—N1	1.415 (2)	C22—H22	0.9300
C8—C9	1.370 (3)	C23—C24	1.352 (3)
C8—H8	0.9300	C23—H23	0.9300
C9—C10	1.357 (3)	C24—C25	1.406 (3)
C9—H9	0.9300	C24—H24	0.9300
C10—C11	1.368 (3)	C25—C26	1.414 (3)
C10—H10	0.9300	C25—C30	1.415 (3)
C11—C12	1.385 (3)	C26—C27	1.351 (3)
C11—H11	0.9300	C26—H26	0.9300
C12—H12	0.9300	C27—C28	1.386 (3)
C13—C18	1.385 (3)	C27—H27	0.9300
C13—C14	1.387 (3)	C28—C29	1.360 (3)
C13—N1	1.413 (2)	C28—H28	0.9300
C14—C15	1.375 (3)	C29—C30	1.407 (3)
C14—H14	0.9300	C29—H29	0.9300
C6—C1—C2	118.8 (2)	C15—C16—C19	122.93 (18)
C6—C1—N1	120.5 (2)	C18—C17—C16	122.32 (18)
C2—C1—N1	120.70 (19)	C18—C17—H17	118.8
C3—C2—C1	120.8 (2)	C16—C17—H17	118.8
C3—C2—H2	119.6	C17—C18—C13	120.08 (19)
C1—C2—H2	119.6	C17—C18—H18	120.0
C4—C3—C2	120.8 (3)	C13—C18—H18	120.0
C4—C3—H3	119.6	C20—C19—C16	128.28 (19)
C2—C3—H3	119.6	C20—C19—H19	115.9
C3—C4—C5	119.8 (3)	C16—C19—H19	115.9
C3—C4—H4	120.1	C19—C20—C21	125.47 (18)
C5—C4—H4	120.1	C19—C20—H20	117.3
C4—C5—C6	120.5 (3)	C21—C20—H20	117.3
C4—C5—H5	119.8	C22—C21—C30	118.49 (18)
C6—C5—H5	119.8	C22—C21—C20	120.73 (18)
C1—C6—C5	119.3 (3)	C30—C21—C20	120.78 (17)
C1—C6—H6	120.3	C21—C22—C23	121.6 (2)
C5—C6—H6	120.3	C21—C22—H22	119.2
C8—C7—C12	118.6 (2)	C23—C22—H22	119.2
C8—C7—N1	120.78 (19)	C24—C23—C22	120.6 (2)
C12—C7—N1	120.58 (19)	C24—C23—H23	119.7
C9—C8—C7	120.5 (2)	C22—C23—H23	119.7
C9—C8—H8	119.7	C23—C24—C25	120.6 (2)
C7—C8—H8	119.7	C23—C24—H24	119.7
C10—C9—C8	121.1 (2)	C25—C24—H24	119.7
C10—C9—H9	119.4	C24—C25—C26	121.8 (2)
C8—C9—H9	119.4	C24—C25—C30	119.2 (2)
C9—C10—C11	119.3 (2)	C26—C25—C30	119.0 (2)
C9—C10—H10	120.4	C27—C26—C25	121.2 (2)
C11—C10—H10	120.4	C27—C26—H26	119.4
C10—C11—C12	120.4 (2)	C25—C26—H26	119.4
C10—C11—H11	119.8	C26—C27—C28	120.0 (2)
C12—C11—H11	119.8	C26—C27—H27	120.0
C7—C12—C11	120.0 (2)	C28—C27—H27	120.0
C7—C12—H12	120.0	C29—C28—C27	120.4 (2)
C11—C12—H12	120.0	C29—C28—H28	119.8
C18—C13—C14	118.43 (18)	C27—C28—H28	119.8
C18—C13—N1	120.87 (18)	C28—C29—C30	121.8 (2)
C14—C13—N1	120.70 (18)	C28—C29—H29	119.1
C15—C14—C13	120.99 (18)	C30—C29—H29	119.1
C15—C14—H14	119.5	C29—C30—C25	117.49 (19)
C13—C14—H14	119.5	C29—C30—C21	122.95 (17)
C14—C15—C16	121.34 (18)	C25—C30—C21	119.51 (18)
C14—C15—H15	119.3	C13—N1—C1	119.80 (16)
C16—C15—H15	119.3	C13—N1—C7	120.46 (16)
C17—C16—C15	116.82 (17)	C1—N1—C7	119.65 (16)
C17—C16—C19	120.25 (17)
C6—C1—C2—C3	−0.6 (3)	C20—C21—C22—C23	179.08 (19)
N1—C1—C2—C3	179.70 (19)	C21—C22—C23—C24	0.0 (3)
C1—C2—C3—C4	−0.6 (4)	C22—C23—C24—C25	−0.1 (3)
C2—C3—C4—C5	0.9 (4)	C23—C24—C25—C26	−177.6 (2)
C3—C4—C5—C6	−0.1 (4)	C23—C24—C25—C30	0.9 (3)
C2—C1—C6—C5	1.4 (3)	C24—C25—C26—C27	179.2 (2)
N1—C1—C6—C5	−178.91 (19)	C30—C25—C26—C27	0.7 (3)
C4—C5—C6—C1	−1.1 (4)	C25—C26—C27—C28	−0.4 (3)
C12—C7—C8—C9	0.5 (3)	C26—C27—C28—C29	−0.1 (3)
N1—C7—C8—C9	−179.93 (19)	C27—C28—C29—C30	0.3 (3)
C7—C8—C9—C10	−0.6 (3)	C28—C29—C30—C25	0.0 (3)
C8—C9—C10—C11	0.0 (4)	C28—C29—C30—C21	−177.45 (18)
C9—C10—C11—C12	0.8 (3)	C24—C25—C30—C29	−178.97 (17)
C8—C7—C12—C11	0.2 (3)	C26—C25—C30—C29	−0.5 (3)
N1—C7—C12—C11	−179.35 (18)	C24—C25—C30—C21	−1.5 (3)
C10—C11—C12—C7	−0.9 (3)	C26—C25—C30—C21	177.05 (17)
C18—C13—C14—C15	0.9 (3)	C22—C21—C30—C29	178.70 (17)
N1—C13—C14—C15	−179.02 (18)	C20—C21—C30—C29	−1.0 (3)
C13—C14—C15—C16	0.2 (3)	C22—C21—C30—C25	1.3 (3)
C14—C15—C16—C17	−0.9 (3)	C20—C21—C30—C25	−178.36 (16)
C14—C15—C16—C19	179.05 (17)	C18—C13—N1—C1	−140.1 (2)
C15—C16—C17—C18	0.6 (3)	C14—C13—N1—C1	39.8 (3)
C19—C16—C17—C18	−179.41 (18)	C18—C13—N1—C7	43.2 (3)
C16—C17—C18—C13	0.5 (3)	C14—C13—N1—C7	−136.9 (2)
C14—C13—C18—C17	−1.2 (3)	C6—C1—N1—C13	47.9 (3)
N1—C13—C18—C17	178.68 (17)	C2—C1—N1—C13	−132.4 (2)
C17—C16—C19—C20	174.2 (2)	C6—C1—N1—C7	−135.4 (2)
C15—C16—C19—C20	−5.8 (3)	C2—C1—N1—C7	44.3 (3)
C16—C19—C20—C21	178.50 (17)	C8—C7—N1—C13	44.3 (3)
C19—C20—C21—C22	−39.4 (3)	C12—C7—N1—C13	−136.2 (2)
C19—C20—C21—C30	140.3 (2)	C8—C7—N1—C1	−132.4 (2)
C30—C21—C22—C23	−0.6 (3)	C12—C7—N1—C1	47.2 (3)