Literature DB >> 21587990

2,4,6-Triphenyl-aniline.

Onome Ugono¹, Stephanie Cowin, Alicia M Beatty.

Abstract

Individual mol-ecules of the title compound, C(24)H(19)N, do not participate in hydrogen-bonding inter-actions due to the steric bulk of the phenyl rings ortho to the amine. The dihedral angles between the central ring and the pendant rings are 68.26 (10), 55.28 (10) and 30.61 (11)°.

Entities: Chemical Disease Gene

Year: 2010 PMID： 21587990 PMCID： PMC3006753 DOI： 10.1107/S160053681002338X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

The reaction of equimolar amounts of pyrazole-3,5-dicarboxylic acid (HPzDCA) and primary amines have yielded ammonium carboxylate salts that adopt layered architectures, see: Ugono et al. (2009 ▶); Beatty et al. (2002a ▶,b ▶). For other amines that do not exhibit intermolecular hydrogen bonding due to the bulky ortho phenyl groups, see: Cherian et al. (2005 ▶); Lonkin & Marshal (2004 ▶). For the preparation of 2,4,6-triphenylaniline, see: Basu et al. (2003 ▶); Paul & Clark (2003 ▶).

Experimental

Crystal data

C24H19N M = 321.40 Monoclinic, a = 10.735 (2) Å b = 14.792 (3) Å c = 11.911 (2) Å β = 113.02 (3)° V = 1740.7 (6) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 100 K 0.50 × 0.50 × 0.25 mm

Data collection

Bruker SMART APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.966, T max = 0.983 44061 measured reflections 6695 independent reflections 5813 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.125 S = 1.02 6695 reflections 226 parameters H-atom parameters constrained Δρmax = 0.48 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S160053681002338X/hg2686sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053681002338X/hg2686Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₂₄H₁₉N	F(000) = 680
M_r = 321.40	D_x = 1.226 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 395–398 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.735 (2) Å	Cell parameters from 6695 reflections
b = 14.792 (3) Å	θ = 2.1–33.9°
c = 11.911 (2) Å	µ = 0.07 mm⁻¹
β = 113.02 (3)°	T = 100 K
V = 1740.7 (6) Å³	Prism, colorless
Z = 4	0.50 × 0.50 × 0.25 mm

Bruker SMART APEXII diffractometer	6695 independent reflections
Radiation source: fine-focus sealed tube	5813 reflections with I > 2σ(I)
graphite	R_int = 0.027
ω scans	θ_max = 33.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.966, T_max = 0.983	k = −23→23
44061 measured reflections	l = −18→18

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0697P)² + 0.5511P] where P = (F_o² + 2F_c²)/3
6695 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
N1	−0.03946 (8)	0.31892 (6)	0.10628 (7)	0.02312 (15)
H1A	−0.0309	0.3532	0.1693	0.028*
H1B	−0.1086	0.2817	0.0760	0.028*
C1	0.05584 (7)	0.32362 (5)	0.05479 (6)	0.01365 (13)
C2	0.16729 (8)	0.38320 (5)	0.10276 (7)	0.01385 (13)
C3	0.26324 (8)	0.38694 (5)	0.05077 (7)	0.01493 (13)
H3	0.3376	0.4272	0.0842	0.018*
C4	0.25338 (7)	0.33322 (5)	−0.04924 (7)	0.01409 (13)
C5	0.14616 (7)	0.27160 (5)	−0.09177 (7)	0.01405 (13)
H5	0.1399	0.2322	−0.1567	0.017*
C6	0.04796 (7)	0.26577 (5)	−0.04244 (6)	0.01310 (13)
C7	0.18451 (8)	0.44422 (5)	0.20775 (7)	0.01407 (13)
C8	0.29191 (8)	0.43079 (5)	0.32071 (7)	0.01645 (14)
H8	0.3517	0.3812	0.3314	0.020*
C9	0.31156 (8)	0.48981 (6)	0.41751 (7)	0.01874 (15)
H9	0.3837	0.4796	0.4941	0.022*
C10	0.22601 (9)	0.56362 (6)	0.40238 (7)	0.01889 (15)
H10	0.2404	0.6042	0.4681	0.023*
C11	0.11933 (9)	0.57760 (6)	0.29049 (7)	0.01905 (15)
H11	0.0609	0.6280	0.2797	0.023*
C12	0.09793 (9)	0.51788 (5)	0.19407 (7)	0.01751 (14)
H12	0.0239	0.5273	0.1184	0.021*
C13	0.34837 (8)	0.34425 (5)	−0.11131 (7)	0.01444 (13)
C14	0.48238 (8)	0.37311 (6)	−0.04755 (7)	0.01809 (14)
H14	0.5146	0.3829	0.0380	0.022*
C15	0.56863 (8)	0.38749 (6)	−0.10796 (8)	0.02019 (15)
H15	0.6589	0.4071	−0.0633	0.024*
C16	0.52351 (9)	0.37333 (6)	−0.23338 (8)	0.02020 (15)
H16	0.5819	0.3842	−0.2747	0.024*
C17	0.39142 (9)	0.34296 (6)	−0.29744 (8)	0.01904 (15)
H17	0.3603	0.3318	−0.3826	0.023*
C18	0.30489 (8)	0.32897 (5)	−0.23725 (7)	0.01613 (14)
H18	0.2150	0.3088	−0.2821	0.019*
C19	−0.06390 (7)	0.19929 (5)	−0.09729 (6)	0.01294 (12)
C20	−0.19933 (8)	0.22763 (5)	−0.14897 (7)	0.01598 (14)
H20	−0.2206	0.2894	−0.1433	0.019*
C21	−0.30318 (8)	0.16641 (5)	−0.20861 (7)	0.01793 (14)
H21	−0.3944	0.1866	−0.2431	0.022*
C22	−0.27334 (8)	0.07567 (5)	−0.21765 (7)	0.01761 (14)
H22	−0.3438	0.0339	−0.2587	0.021*
C23	−0.13918 (8)	0.04676 (5)	−0.16595 (7)	0.01747 (14)
H23	−0.1184	−0.0151	−0.1715	0.021*
C24	−0.03506 (8)	0.10781 (5)	−0.10612 (7)	0.01537 (13)
H24	0.0559	0.0872	−0.0712	0.018*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0255 (3)	0.0285 (4)	0.0204 (3)	−0.0110 (3)	0.0144 (3)	−0.0100 (3)
C1	0.0160 (3)	0.0130 (3)	0.0116 (3)	−0.0006 (2)	0.0051 (2)	0.0004 (2)
C2	0.0169 (3)	0.0120 (3)	0.0117 (3)	−0.0010 (2)	0.0047 (2)	−0.0007 (2)
C3	0.0165 (3)	0.0133 (3)	0.0141 (3)	−0.0019 (2)	0.0050 (2)	−0.0016 (2)
C4	0.0147 (3)	0.0134 (3)	0.0139 (3)	−0.0009 (2)	0.0053 (2)	−0.0010 (2)
C5	0.0153 (3)	0.0124 (3)	0.0139 (3)	−0.0006 (2)	0.0052 (2)	−0.0015 (2)
C6	0.0146 (3)	0.0112 (3)	0.0123 (3)	−0.0006 (2)	0.0040 (2)	−0.0001 (2)
C7	0.0177 (3)	0.0130 (3)	0.0113 (3)	−0.0022 (2)	0.0054 (2)	−0.0006 (2)
C8	0.0166 (3)	0.0180 (3)	0.0134 (3)	−0.0012 (2)	0.0045 (2)	−0.0003 (2)
C9	0.0196 (3)	0.0231 (4)	0.0123 (3)	−0.0046 (3)	0.0049 (3)	−0.0016 (3)
C10	0.0253 (4)	0.0192 (3)	0.0140 (3)	−0.0058 (3)	0.0095 (3)	−0.0039 (3)
C11	0.0268 (4)	0.0151 (3)	0.0165 (3)	0.0002 (3)	0.0098 (3)	−0.0012 (2)
C12	0.0229 (3)	0.0148 (3)	0.0132 (3)	0.0011 (3)	0.0052 (3)	0.0004 (2)
C13	0.0153 (3)	0.0125 (3)	0.0155 (3)	−0.0007 (2)	0.0060 (2)	−0.0011 (2)
C14	0.0154 (3)	0.0195 (3)	0.0182 (3)	−0.0013 (2)	0.0054 (3)	−0.0018 (3)
C15	0.0159 (3)	0.0192 (3)	0.0262 (4)	−0.0002 (3)	0.0090 (3)	−0.0002 (3)
C16	0.0214 (4)	0.0173 (3)	0.0264 (4)	0.0023 (3)	0.0142 (3)	0.0026 (3)
C17	0.0245 (4)	0.0166 (3)	0.0186 (3)	0.0012 (3)	0.0112 (3)	0.0001 (3)
C18	0.0181 (3)	0.0144 (3)	0.0158 (3)	−0.0012 (2)	0.0065 (3)	−0.0017 (2)
C19	0.0153 (3)	0.0117 (3)	0.0117 (3)	−0.0009 (2)	0.0052 (2)	0.0001 (2)
C20	0.0162 (3)	0.0129 (3)	0.0166 (3)	0.0004 (2)	0.0041 (2)	0.0001 (2)
C21	0.0162 (3)	0.0162 (3)	0.0178 (3)	−0.0010 (2)	0.0028 (3)	0.0006 (2)
C22	0.0189 (3)	0.0152 (3)	0.0167 (3)	−0.0041 (2)	0.0048 (3)	−0.0012 (2)
C23	0.0204 (3)	0.0123 (3)	0.0204 (3)	−0.0017 (2)	0.0088 (3)	−0.0018 (2)
C24	0.0168 (3)	0.0124 (3)	0.0176 (3)	−0.0007 (2)	0.0075 (3)	−0.0006 (2)

N1—C1	1.3850 (11)	C12—H12	0.9500
N1—H1A	0.8800	C13—C18	1.4040 (11)
N1—H1B	0.8800	C13—C14	1.4050 (11)
C1—C2	1.4142 (11)	C14—C15	1.3933 (12)
C1—C6	1.4156 (10)	C14—H14	0.9500
C2—C3	1.3951 (11)	C15—C16	1.3944 (13)
C2—C7	1.4939 (11)	C15—H15	0.9500
C3—C4	1.4010 (11)	C16—C17	1.3960 (13)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.3987 (10)	C17—C18	1.3930 (12)
C4—C13	1.4841 (11)	C17—H17	0.9500
C5—C6	1.3959 (11)	C18—H18	0.9500
C5—H5	0.9500	C19—C24	1.4012 (11)
C6—C19	1.4907 (10)	C19—C20	1.4030 (11)
C7—C12	1.3997 (11)	C20—C21	1.3958 (11)
C7—C8	1.4020 (12)	C20—H20	0.9500
C8—C9	1.3950 (11)	C21—C22	1.3939 (12)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.3923 (13)	C22—C23	1.3938 (12)
C9—H9	0.9500	C22—H22	0.9500
C10—C11	1.3916 (13)	C23—C24	1.3962 (11)
C10—H10	0.9500	C23—H23	0.9500
C11—C12	1.3949 (11)	C24—H24	0.9500
C11—H11	0.9500

C1—N1—H1A	120.0	C7—C12—H12	119.7
C1—N1—H1B	120.0	C18—C13—C14	117.95 (8)
H1A—N1—H1B	120.0	C18—C13—C4	120.56 (7)
N1—C1—C2	120.47 (7)	C14—C13—C4	121.46 (7)
N1—C1—C6	120.92 (7)	C15—C14—C13	120.93 (8)
C2—C1—C6	118.53 (7)	C15—C14—H14	119.5
C3—C2—C1	120.01 (7)	C13—C14—H14	119.5
C3—C2—C7	118.45 (7)	C14—C15—C16	120.51 (8)
C1—C2—C7	121.53 (7)	C14—C15—H15	119.7
C2—C3—C4	122.11 (7)	C16—C15—H15	119.7
C2—C3—H3	118.9	C15—C16—C17	119.14 (8)
C4—C3—H3	118.9	C15—C16—H16	120.4
C5—C4—C3	117.09 (7)	C17—C16—H16	120.4
C5—C4—C13	121.31 (7)	C18—C17—C16	120.38 (8)
C3—C4—C13	121.54 (7)	C18—C17—H17	119.8
C6—C5—C4	122.53 (7)	C16—C17—H17	119.8
C6—C5—H5	118.7	C17—C18—C13	121.06 (8)
C4—C5—H5	118.7	C17—C18—H18	119.5
C5—C6—C1	119.59 (7)	C13—C18—H18	119.5
C5—C6—C19	117.89 (6)	C24—C19—C20	118.49 (7)
C1—C6—C19	122.51 (7)	C24—C19—C6	120.41 (7)
C12—C7—C8	118.77 (7)	C20—C19—C6	120.94 (7)
C12—C7—C2	120.91 (7)	C21—C20—C19	120.92 (7)
C8—C7—C2	120.26 (7)	C21—C20—H20	119.5
C9—C8—C7	120.42 (8)	C19—C20—H20	119.5
C9—C8—H8	119.8	C22—C21—C20	120.14 (7)
C7—C8—H8	119.8	C22—C21—H21	119.9
C10—C9—C8	120.33 (8)	C20—C21—H21	119.9
C10—C9—H9	119.8	C23—C22—C21	119.36 (7)
C8—C9—H9	119.8	C23—C22—H22	120.3
C11—C10—C9	119.64 (7)	C21—C22—H22	120.3
C11—C10—H10	120.2	C22—C23—C24	120.65 (7)
C9—C10—H10	120.2	C22—C23—H23	119.7
C10—C11—C12	120.22 (8)	C24—C23—H23	119.7
C10—C11—H11	119.9	C23—C24—C19	120.44 (7)
C12—C11—H11	119.9	C23—C24—H24	119.8
C11—C12—C7	120.61 (8)	C19—C24—H24	119.8
C11—C12—H12	119.7

4 in total

1. Acid-catalyzed ortho-alkylation of anilines with styrenes: an improved route to chiral anilines with bulky substituents.

Authors: Anna E Cherian; Gregory J Domski; Jeffrey M Rose; Emil B Lobkovsky; Geoffrey W Coates
Journal: Org Lett Date: 2005-11-10 Impact factor: 6.005