4-(Diphenyl­amino)benzaldehyde

Wang, H.; Xu, W.; Zhang, B.; Xiao, W.; Wu, H.

doi:10.1107/S1600536808042311

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o149

doi:10.1107/S1600536808042311

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4-(Diphenylamino)benzaldehyde

Hongli Wang,^a ^* Wenyuan Xu,^a Bin Zhang,^a Wenjing Xiao ^a and Hong Wu ^a

^aDepartment of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China
^*Correspondence e-mail: hlwang@mail.ccnu.edu.cn

(Received 13 November 2008; accepted 12 December 2008; online 17 December 2008)

In the title compound, C₁₉H₁₅NO, the N atom adopts an approximately trigonal-planar geometry, lying 0.07 (1) Å from the plane defined by its three neighbouring C atoms. The two phenyl rings and the benzaldehyde group form dihedral angles of 53.0 (1)/47.2 (1) and 29.0 (1)°, respectively, with this central plane.

Related literature

For details of the synthesis, see: Wang & Zhou (2000 ). For arylamines, see: Beller (1995 ); Wang et al. (2005 ); Yao et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₅NO
M_r = 273.32
Monoclinic, P 2₁ /c
a = 12.1188 (8) Å
b = 11.4342 (8) Å
c = 10.9560 (7) Å
β = 102.082 (2)°
V = 1484.53 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 292 (2) K
0.40 × 0.10 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.971, T_max = 0.997
12673 measured reflections
2898 independent reflections
1393 reflections with I > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.153
S = 0.91
2898 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042311/bi2326sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808042311/bi2326Isup2.hkl

checkCIF report

Comment top

Arylamine derivatives are common intermediates in the synthesis of many compounds and polymers (Yao et al., 2006; Beller, 1995). We became interested in using the Vilsmeier reaction to obtain the title compound, which is a good intermediate for several compounds (Wang et al., 2005). In the crystal structure (Fig. 1), the bond lengths and angles are within normal ranges.

Related literature top

For details of the synthesis, see: Wang & Zhou (2000). For arylamines, see: Beller (1995); Wang et al. (2005); Yao et al. (2006).

Experimental top

The title compound was synthesised according to the published procedure (Wang & Zhou, 2000) and recrystallized from chloroform.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound showing displacement ellipsoids at 50% probability for non-H atoms.

4-(Diphenylamino)benzaldehyde top

Crystal data top

C₁₉H₁₅NO	F(000) = 576
M_r = 273.32	D_x = 1.223 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 843 reflections
a = 12.1188 (8) Å	θ = 2.6–18.1°
b = 11.4342 (8) Å	µ = 0.08 mm⁻¹
c = 10.9560 (7) Å	T = 292 K
β = 102.082 (2)°	Needle, colorless
V = 1484.53 (17) Å³	0.40 × 0.10 × 0.04 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2898 independent reflections
Radiation source: fine-focus sealed tube	1393 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
T_min = 0.971, T_max = 0.997	k = −14→14
12673 measured reflections	l = −13→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.153	w = 1/[σ²(F_o²) + (0.0688P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
2898 reflections	Δρ_max = 0.14 e Å⁻³
191 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.007 (2)

Crystal data top

C₁₉H₁₅NO	V = 1484.53 (17) Å³
M_r = 273.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1188 (8) Å	µ = 0.08 mm⁻¹
b = 11.4342 (8) Å	T = 292 K
c = 10.9560 (7) Å	0.40 × 0.10 × 0.04 mm
β = 102.082 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2898 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1393 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.997	R_int = 0.087
12673 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 0.91	Δρ_max = 0.14 e Å⁻³
2898 reflections	Δρ_min = −0.14 e Å⁻³
191 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

	x	y	z	U_iso*/U_eq
C1	0.7834 (2)	0.14287 (18)	0.0025 (2)	0.0483 (7)
C2	0.6819 (2)	0.09360 (19)	0.0112 (3)	0.0587 (8)
H2	0.6307	0.1360	0.0460	0.070*
C3	0.6555 (2)	−0.0192 (2)	−0.0318 (3)	0.0624 (8)
H3	0.5864	−0.0520	−0.0266	0.075*
C4	0.7312 (3)	−0.0821 (2)	−0.0817 (3)	0.0637 (8)
H4	0.7136	−0.1578	−0.1102	0.076*
C5	0.8329 (3)	−0.0340 (2)	−0.0896 (3)	0.0659 (8)
H5	0.8841	−0.0771	−0.1238	0.079*
C6	0.8601 (2)	0.0793 (2)	−0.0468 (2)	0.0574 (7)
H6	0.9295	0.1116	−0.0514	0.069*
C7	0.9178 (2)	0.27936 (18)	0.1276 (2)	0.0492 (7)
C8	0.9540 (2)	0.2101 (2)	0.2309 (3)	0.0645 (8)
H8	0.9076	0.1514	0.2505	0.077*
C9	1.0605 (3)	0.2283 (3)	0.3059 (3)	0.0787 (9)
H9	1.0850	0.1817	0.3759	0.094*
C10	1.1294 (3)	0.3147 (3)	0.2769 (3)	0.0790 (10)
H10	1.2007	0.3263	0.3267	0.095*
C11	1.0929 (3)	0.3832 (2)	0.1750 (3)	0.0811 (10)
H11	1.1392	0.4421	0.1555	0.097*
C12	0.9878 (2)	0.3656 (2)	0.1008 (3)	0.0639 (8)
H12	0.9638	0.4128	0.0312	0.077*
C13	0.7402 (2)	0.35282 (17)	−0.0019 (2)	0.0475 (6)
C14	0.6713 (2)	0.34636 (19)	−0.1196 (3)	0.0593 (7)
H14	0.6724	0.2797	−0.1679	0.071*
C15	0.6009 (2)	0.43842 (19)	−0.1657 (3)	0.0612 (8)
H15	0.5539	0.4320	−0.2442	0.073*
C16	0.5989 (2)	0.53936 (19)	−0.0979 (3)	0.0556 (7)
C17	0.6677 (2)	0.5467 (2)	0.0200 (3)	0.0605 (8)
H17	0.6668	0.6142	0.0673	0.073*
C18	0.7375 (2)	0.45501 (19)	0.0682 (3)	0.0577 (7)
H18	0.7830	0.4610	0.1476	0.069*
C19	0.5231 (2)	0.6343 (2)	−0.1488 (3)	0.0772 (9)
H19	0.4757	0.6210	−0.2260	0.093*
N1	0.81100 (18)	0.25939 (15)	0.0479 (2)	0.0567 (6)
O1	0.51528 (17)	0.72793 (15)	−0.1018 (2)	0.0929 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0461 (16)	0.0370 (12)	0.0592 (17)	0.0004 (11)	0.0050 (14)	0.0024 (11)
C2	0.0541 (17)	0.0434 (14)	0.078 (2)	0.0030 (12)	0.0132 (15)	−0.0002 (13)
C3	0.0542 (18)	0.0487 (15)	0.080 (2)	−0.0060 (13)	0.0049 (17)	0.0013 (13)
C4	0.070 (2)	0.0444 (14)	0.069 (2)	0.0000 (15)	−0.0034 (17)	−0.0046 (13)
C5	0.077 (2)	0.0587 (17)	0.0599 (19)	0.0171 (15)	0.0085 (17)	−0.0094 (13)
C6	0.0515 (17)	0.0579 (15)	0.0632 (19)	−0.0006 (13)	0.0126 (15)	0.0002 (13)
C7	0.0497 (17)	0.0421 (13)	0.0533 (17)	−0.0006 (12)	0.0052 (14)	−0.0027 (12)
C8	0.063 (2)	0.0678 (17)	0.063 (2)	0.0082 (14)	0.0146 (17)	0.0088 (15)
C9	0.077 (3)	0.102 (2)	0.054 (2)	0.030 (2)	0.0059 (19)	−0.0009 (17)
C10	0.059 (2)	0.091 (2)	0.080 (3)	0.0012 (19)	−0.001 (2)	−0.035 (2)
C11	0.068 (2)	0.0638 (18)	0.105 (3)	−0.0069 (16)	0.004 (2)	−0.0098 (19)
C12	0.0566 (19)	0.0577 (15)	0.073 (2)	−0.0066 (14)	0.0024 (16)	0.0013 (14)
C13	0.0466 (16)	0.0380 (12)	0.0558 (17)	−0.0024 (11)	0.0063 (14)	−0.0006 (11)
C14	0.0660 (19)	0.0441 (14)	0.0625 (19)	0.0027 (12)	0.0010 (16)	−0.0066 (12)
C15	0.0591 (18)	0.0515 (15)	0.0662 (19)	0.0039 (13)	−0.0025 (15)	0.0006 (13)
C16	0.0484 (17)	0.0430 (14)	0.073 (2)	0.0013 (11)	0.0066 (16)	0.0000 (13)
C17	0.0591 (18)	0.0417 (14)	0.081 (2)	−0.0023 (13)	0.0158 (17)	−0.0126 (13)
C18	0.0561 (18)	0.0489 (14)	0.0638 (19)	0.0003 (12)	0.0027 (15)	−0.0047 (13)
C19	0.077 (2)	0.0477 (16)	0.103 (3)	0.0085 (15)	0.0115 (19)	0.0079 (16)
N1	0.0526 (14)	0.0375 (10)	0.0714 (16)	0.0000 (9)	−0.0067 (12)	0.0017 (10)
O1	0.0878 (16)	0.0471 (11)	0.143 (2)	0.0126 (10)	0.0210 (15)	−0.0011 (11)

Geometric parameters (Å, º) top

C1—C2	1.375 (3)	C10—C11	1.359 (4)
C1—C6	1.376 (3)	C10—H10	0.930
C1—N1	1.437 (3)	C11—C12	1.375 (3)
C2—C3	1.387 (3)	C11—H11	0.930
C2—H2	0.930	C12—H12	0.930
C3—C4	1.366 (4)	C13—C14	1.383 (3)
C3—H3	0.930	C13—C18	1.402 (3)
C4—C5	1.369 (4)	C13—N1	1.407 (3)
C4—H4	0.930	C14—C15	1.382 (3)
C5—C6	1.394 (3)	C14—H14	0.930
C5—H5	0.930	C15—C16	1.376 (3)
C6—H6	0.930	C15—H15	0.930
C7—C12	1.372 (3)	C16—C17	1.385 (4)
C7—C8	1.375 (3)	C16—C19	1.456 (3)
C7—N1	1.421 (3)	C17—C18	1.381 (3)
C8—C9	1.392 (4)	C17—H17	0.930
C8—H8	0.930	C18—H18	0.930
C9—C10	1.373 (4)	C19—O1	1.200 (3)
C9—H9	0.930	C19—H19	0.930

C2—C1—C6	119.9 (2)	C10—C11—C12	120.2 (3)
C2—C1—N1	120.2 (2)	C10—C11—H11	119.9
C6—C1—N1	119.9 (2)	C12—C11—H11	119.9
C1—C2—C3	120.2 (2)	C7—C12—C11	121.1 (3)
C1—C2—H2	119.9	C7—C12—H12	119.5
C3—C2—H2	119.9	C11—C12—H12	119.5
C4—C3—C2	119.9 (3)	C14—C13—C18	118.4 (2)
C4—C3—H3	120.0	C14—C13—N1	121.4 (2)
C2—C3—H3	120.0	C18—C13—N1	120.2 (2)
C3—C4—C5	120.2 (2)	C15—C14—C13	120.4 (2)
C3—C4—H4	119.9	C15—C14—H14	119.8
C5—C4—H4	119.9	C13—C14—H14	119.8
C4—C5—C6	120.3 (3)	C16—C15—C14	121.4 (3)
C4—C5—H5	119.9	C16—C15—H15	119.3
C6—C5—H5	119.9	C14—C15—H15	119.3
C1—C6—C5	119.5 (2)	C15—C16—C17	118.6 (2)
C1—C6—H6	120.3	C15—C16—C19	120.0 (3)
C5—C6—H6	120.3	C17—C16—C19	121.3 (2)
C12—C7—C8	119.0 (3)	C18—C17—C16	120.7 (2)
C12—C7—N1	120.6 (2)	C18—C17—H17	119.6
C8—C7—N1	120.4 (2)	C16—C17—H17	119.6
C7—C8—C9	119.8 (3)	C17—C18—C13	120.4 (3)
C7—C8—H8	120.1	C17—C18—H18	119.8
C9—C8—H8	120.1	C13—C18—H18	119.8
C10—C9—C8	120.2 (3)	O1—C19—C16	126.9 (3)
C10—C9—H9	119.9	O1—C19—H19	116.5
C8—C9—H9	119.9	C16—C19—H19	116.5
C11—C10—C9	119.7 (3)	C13—N1—C7	121.32 (18)
C11—C10—H10	120.1	C13—N1—C1	119.4 (2)
C9—C10—H10	120.1	C7—N1—C1	118.55 (18)

C6—C1—C2—C3	−1.3 (4)	C14—C15—C16—C19	−179.6 (3)
N1—C1—C2—C3	−179.5 (2)	C15—C16—C17—C18	0.5 (4)
C1—C2—C3—C4	0.7 (4)	C19—C16—C17—C18	178.7 (2)
C2—C3—C4—C5	−0.2 (4)	C16—C17—C18—C13	0.3 (4)
C3—C4—C5—C6	0.1 (4)	C14—C13—C18—C17	−0.2 (4)
C2—C1—C6—C5	1.2 (4)	N1—C13—C18—C17	−179.6 (2)
N1—C1—C6—C5	179.5 (2)	C15—C16—C19—O1	−177.5 (3)
C4—C5—C6—C1	−0.7 (4)	C17—C16—C19—O1	4.4 (5)
C12—C7—C8—C9	−0.1 (4)	C14—C13—N1—C7	146.1 (2)
N1—C7—C8—C9	177.9 (2)	C18—C13—N1—C7	−34.5 (4)
C7—C8—C9—C10	−0.2 (4)	C14—C13—N1—C1	−23.9 (4)
C8—C9—C10—C11	0.5 (4)	C18—C13—N1—C1	155.4 (2)
C9—C10—C11—C12	−0.5 (5)	C12—C7—N1—C13	−42.9 (4)
C8—C7—C12—C11	0.1 (4)	C8—C7—N1—C13	139.1 (2)
N1—C7—C12—C11	−177.9 (2)	C12—C7—N1—C1	127.3 (2)
C10—C11—C12—C7	0.2 (4)	C8—C7—N1—C1	−50.7 (3)
C18—C13—C14—C15	−0.6 (4)	C2—C1—N1—C13	−58.8 (3)
N1—C13—C14—C15	178.8 (2)	C6—C1—N1—C13	123.0 (3)
C13—C14—C15—C16	1.4 (4)	C2—C1—N1—C7	130.9 (3)
C14—C15—C16—C17	−1.4 (4)	C6—C1—N1—C7	−47.4 (3)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅NO
M_r	273.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	292
a, b, c (Å)	12.1188 (8), 11.4342 (8), 10.9560 (7)
β (°)	102.082 (2)
V (Å³)	1484.53 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.10 × 0.04

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.971, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	12673, 2898, 1393
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.153, 0.91
No. of reflections	2898
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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