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Shaped like a distorted propeller, mol­ecules of the title compound, C19H15NO2, form centrosymmetric dimers in the crystalline phase in which the carboxy groups are linked through two hydrogen bonds. These dimers are arranged in columns held together via dispersive interactions between the phenyl moieties. The N atom and the three surrounding C atoms lie almost in the same plane, which implies that the lone electron pair of the N atom is involved in conjugation with the [pi] systems of the phenyl fragments.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101008459/sk1456sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101008459/sk1456Isup2.hkl
Contains datablock I

CCDC reference: 170209

Comment top

Triphenylamine is a unique aromatic amine in which three phenyl substituents are attached to the N atom. The large size of the substituents means that all three C—N—C angles are ca 120° and that the N atom and the three adjacent C atoms lie in a single plane (Sobolev et al., 1985). The phenyl substituents surround the N atom, taking up an irregular propeller-like shape (Table 1). For such a structure, one may expect that the lone electron pair of the N atom occupies the p orbital perpendicular to the plane formed by the four central atoms and conjugates with the phenyl moieties of the substituents. This lone electron pair is less available to the proton, so the proton affinity of triphenylamine is lower than that of the majority of aromatic or aliphatic amines (Ikuta & Kebarle, 1983). If the phenyl fragments are substituted, the distortion from the regular propeller structure depends on the size and character of the atoms or groups attached to them. However, the phenyl substituents in tri(2-methoxyphenyl)amine surround the N atom, taking up a regular propeller-like shape (Table 1). To our knowledge, the structures of more than ten compounds (some are listed in Table 1) originating from triphenylamine have been established so far and none of them contains a group able to participate in strong hydrogen-bonding interactions. The title compound, (I), which we synthesized contains a carboxy group and it was our intention to explore the extent to which the presence of this group affects the structural and physicochemical features of the crystalline phase. \sch

In the crystalline phase, a molecule of (I) is shaped like a distorted propeller (Fig. 1), since the phenyl substituents are unequally twisted relative to the plane formed by the N and the three neighbouring C atoms (Tables 1 and 2). Note that the C—N—C angles are almost equal (a total of 359.92°) and the N—C bonds spread almost symmetrically from the N atom (Table 2). This means that the N atom is sp2-hybridized and the lone electron pair occupies the p orbital perpendicular to the plane formed by the four central atoms. This lone electron pair is involved in conjugation with the π-aromatic systems of the benzene rings. As a result, the N—C bonds (mean 1.415 Å) are only ca 0.002 Å longer than in aromatic amines and ca 0.054 Å shorter than in aliphatic ones (International Tables for X-ray Crystallography, 1992, vol. C, pp. 685–706).

All the atoms making up the carboxy group lie in a plane that is twisted through an angle of 13.7° relative to the benzene ring (Table 2). The distance between the C atom of the benzene ring and the C atom of the carboxy group is typical for carboxylic acids (International Tables for X-ray Crystallography, 1992, vol. C, pp. 685–706). On the other hand, the O—C distances within this group are almost equal, which suggests that both O atoms are involved in strong hydrogen bonds. Indeed, the arrangement of molecules in the crystalline phase shows that the carboxy groups are bonded via a couple of hydrogen bonds (Fig. 2), whose geometry is the same as in the strong bonds (Table 3). The dimers of (I) formed as a result of hydrogen bonding are arranged in the crystal in columns held via dispersive interactions between the phenyl moieties. These unique structural features of (I) explain the ease of formation and the relatively high stability of its crystalline phase.

Related literature top

For related literature, see: Goldberg & Nimerovsky (1907); Ikuta & Kebarle (1983); Sobolev et al. (1985).

Experimental top

The title compound was synthesized according to the method described by Goldberg & Nimerovsky (1907). Green crystals of (I) suitable for X-ray investigation were grown from ethyl alcohol.

Refinement top

No constraints were applied for H atoms; the mean Car—H distance was 0.965 Å and the refined O—H distance was 1.08 (4) Å. C—H bond lengths were in the range 0.92–1.02 Å and their s.u.s did not exceed 0.03 Å.

Computing details top

Data collection: Kuma KM-4 Software (Kuma Diffraction, 1989); cell refinement: Kuma KM-4 Software; data reduction: Kuma KM-4 Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and with 50% probability displacement ellipsoids. H atoms are drawn as small spheres of arbitrary radii.
[Figure 2] Fig. 2. The packing diagram of (I) in the unit cell viewed along the y axis. Hydrogen bonds are represented by dashed lines.
2-(N,N-diphenylamino)benzoic acid top
Crystal data top
C19H15NO2Z = 2
Mr = 289.32F(000) = 304
Triclinic, P1Dx = 1.282 Mg m3
a = 9.145 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.427 (2) ÅCell parameters from 50 reflections
c = 9.889 (2) Åθ = 6–13°
α = 85.19 (3)°µ = 0.08 mm1
β = 82.64 (3)°T = 293 K
γ = 62.45 (3)°Plate, green
V = 749.3 (3) Å30.5 × 0.3 × 0.3 mm
Data collection top
Kuma KM-4
diffractometer
Rint = 0.036
Radiation source: fine-focus sealed tubeθmax = 30.1°, θmin = 2.1°
Graphite monochromatorh = 1111
θ/2θ scansk = 1212
4376 measured reflectionsl = 130
4175 independent reflections3 standard reflections every 200 reflections
1581 reflections with I > 2σ(I) intensity decay: 22%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151All H-atom parameters refined
S = 1.00 w = 1/[σ2(Fo2) + (0.0699P)2]
where P = (Fo2 + 2Fc2)/3
4175 reflections(Δ/σ)max < 0.001
259 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C19H15NO2γ = 62.45 (3)°
Mr = 289.32V = 749.3 (3) Å3
Triclinic, P1Z = 2
a = 9.145 (2) ÅMo Kα radiation
b = 9.427 (2) ŵ = 0.08 mm1
c = 9.889 (2) ÅT = 293 K
α = 85.19 (3)°0.5 × 0.3 × 0.3 mm
β = 82.64 (3)°
Data collection top
Kuma KM-4
diffractometer
Rint = 0.036
4376 measured reflections3 standard reflections every 200 reflections
4175 independent reflections intensity decay: 22%
1581 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.151All H-atom parameters refined
S = 1.00Δρmax = 0.18 e Å3
4175 reflectionsΔρmin = 0.23 e Å3
259 parameters
Special details top

Geometry. Mean-plane data from final SHELXL refinement run:-

# Plane C-COO

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

8.347 (0.006) x + 2.764 (0.011) y - 2.626 (0.009) z = 4.181 (0.011)

* -0.0141 (0.0016) C19 * 0.0047 (0.0005) O1 * 0.0054 (0.0006) O2 * 0.0041 (0.0005) C2

Rms deviation of fitted atoms = 0.0082

# Plane N-ringA-COO

7.241 (0.006) x + 0.759 (0.008) y - 4.172 (0.008) z = 1.522 (0.010)

Angle to previous plane (with approximate e.s.d.) = 14.61 (0.11)

* -0.0144 (0.0013) C1 * 0.0191 (0.0012) C2 * -0.0079 (0.0013) C3 * -0.0084 (0.0015) C4 * 0.0133 (0.0016) C5 * -0.0017 (0.0015) C6 - 0.1002 (0.0027) N1 0.9638 (0.0036) C7 - 1.2698 (0.0034) C13 0.1417 (0.0029) C19 - 0.0644 (0.0036) O1 0.4642 (0.0033) O2

Rms deviation of fitted atoms = 0.0122

#Plane N—C(ringA)-C(ringB)-C(ringC)

- 1.570 (0.009) x - 4.710 (0.009) y + 8.119 (0.007) z = 4.977 (0.010)

Angle to previous plane (with approximate e.s.d.) = 64.45 (0.08)

* 0.0056 (0.0004) C1 * 0.0060 (0.0005) C7 * 0.0060 (0.0005) C13 * -0.0176 (0.0013) N1

Rms deviation of fitted atoms = 0.0102

# Plane N-ringB

3.480 (0.008) x - 0.072 (0.009) y + 9.261 (0.006) z = 9.423 (0.007)

Angle to previous plane (with approximate e.s.d.) = 35.78 (0.08)

* 0.0048 (0.0014) C7 * -0.0067 (0.0014) C8 * 0.0012 (0.0016) C9 * 0.0064 (0.0018) C10 * -0.0083 (0.0019) C11 * 0.0027 (0.0017) C12 0.0429 (0.0027) N1 - 0.5939 (0.0036) C13 0.8231 (0.0036) C1

Rms deviation of fitted atoms = 0.0056

# Plane N-ringC

- 2.316 (0.008) x - 7.982 (0.007) y + 4.441 (0.010) z = 1.361 (0.010)

Angle to the plane C1 C7 C13 N1 (with approximate e.s.d.) = 29.21 (0.13)

* -0.0025 (0.0015) C13 * -0.0046 (0.0019) C14 * 0.0064 (0.0020) C15 * -0.0010 (0.0018) C16 * -0.0061 (0.0017) C17 * 0.0078 (0.0015) C18 - 0.0306 (0.0029) N1 0.5601 (0.0039) C7 - 0.6249 (0.0036) C1

Rms deviation of fitted atoms = 0.0053

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
N10.63854 (17)0.08359 (17)0.78280 (15)0.0410 (4)
O10.5227 (2)0.56345 (18)0.66037 (18)0.0820 (6)
H10.491 (4)0.592 (4)0.557 (4)0.147 (13)*
O20.57696 (19)0.32822 (17)0.58513 (14)0.0645 (4)
C10.6798 (2)0.1847 (2)0.85232 (17)0.0386 (4)
C20.6426 (2)0.3415 (2)0.80817 (17)0.0379 (4)
C30.6757 (2)0.4351 (2)0.8892 (2)0.0458 (5)
H3A0.652 (3)0.540 (3)0.852 (2)0.063 (6)*
C40.7500 (2)0.3745 (3)1.0073 (2)0.0520 (5)
H4A0.774 (2)0.439 (2)1.059 (2)0.053 (6)*
C50.7922 (3)0.2184 (3)1.0469 (2)0.0588 (6)
H5A0.844 (3)0.176 (3)1.130 (2)0.075 (7)*
C70.7691 (2)0.0585 (2)0.72853 (17)0.0397 (4)
C60.7559 (3)0.1254 (3)0.9706 (2)0.0544 (6)
H6A0.778 (3)0.022 (3)0.996 (2)0.064 (7)*
C80.9161 (2)0.0609 (3)0.6720 (2)0.0482 (5)
H8A0.927 (2)0.039 (2)0.669 (2)0.057 (6)*
C91.0470 (3)0.2005 (3)0.6226 (2)0.0620 (6)
H9A1.145 (3)0.194 (3)0.585 (3)0.082 (8)*
C101.0324 (3)0.3397 (3)0.6276 (3)0.0726 (7)
H10A1.126 (3)0.440 (3)0.587 (3)0.103 (9)*
C110.8856 (4)0.3374 (3)0.6812 (3)0.0757 (8)
H11A0.873 (3)0.436 (3)0.684 (3)0.100 (9)*
C120.7555 (3)0.1997 (3)0.7323 (2)0.0592 (6)
H12A0.652 (3)0.195 (3)0.773 (2)0.074 (7)*
C130.4697 (2)0.1263 (2)0.77782 (17)0.0405 (4)
C140.4170 (3)0.0826 (4)0.6713 (2)0.0718 (7)
H14A0.500 (3)0.025 (3)0.602 (3)0.088 (8)*
C150.2517 (3)0.1263 (4)0.6662 (3)0.0783 (8)
H15A0.221 (3)0.090 (3)0.595 (3)0.105 (9)*
C160.1356 (3)0.2164 (3)0.7659 (3)0.0648 (6)
H16A0.020 (3)0.242 (3)0.763 (2)0.080 (8)*
C170.1858 (3)0.2614 (3)0.8718 (3)0.0626 (6)
H17A0.097 (3)0.323 (3)0.948 (2)0.075 (7)*
C180.3517 (2)0.2156 (2)0.8792 (2)0.0494 (5)
H18A0.389 (3)0.242 (3)0.956 (2)0.070 (7)*
C190.5761 (2)0.4098 (2)0.67586 (19)0.0438 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0389 (9)0.0385 (8)0.0443 (9)0.0145 (7)0.0111 (7)0.0028 (7)
O10.1277 (15)0.0444 (9)0.0619 (11)0.0251 (9)0.0364 (10)0.0136 (7)
O20.0905 (12)0.0547 (9)0.0440 (8)0.0279 (8)0.0203 (7)0.0092 (7)
C10.0370 (9)0.0363 (10)0.0404 (9)0.0138 (8)0.0094 (7)0.0004 (7)
C20.0326 (9)0.0403 (10)0.0386 (9)0.0149 (8)0.0059 (7)0.0034 (8)
C30.0442 (11)0.0388 (11)0.0545 (12)0.0193 (9)0.0027 (9)0.0033 (9)
C40.0482 (12)0.0538 (13)0.0567 (12)0.0223 (10)0.0114 (9)0.0123 (10)
C50.0632 (14)0.0581 (14)0.0532 (13)0.0208 (11)0.0284 (11)0.0001 (10)
C70.0443 (11)0.0387 (10)0.0336 (9)0.0154 (8)0.0113 (8)0.0018 (7)
C60.0681 (14)0.0422 (12)0.0523 (12)0.0209 (10)0.0267 (10)0.0074 (9)
C80.0476 (12)0.0505 (12)0.0456 (11)0.0203 (10)0.0108 (9)0.0001 (9)
C90.0460 (13)0.0723 (17)0.0559 (13)0.0158 (12)0.0056 (10)0.0089 (12)
C100.0681 (17)0.0513 (15)0.0730 (17)0.0047 (13)0.0049 (13)0.0126 (12)
C110.093 (2)0.0415 (13)0.0843 (18)0.0269 (14)0.0085 (15)0.0116 (12)
C120.0678 (15)0.0468 (13)0.0632 (14)0.0287 (11)0.0059 (11)0.0064 (10)
C130.0428 (10)0.0432 (10)0.0368 (9)0.0200 (8)0.0111 (8)0.0051 (8)
C140.0525 (14)0.113 (2)0.0486 (13)0.0338 (14)0.0063 (11)0.0203 (13)
C150.0613 (16)0.119 (2)0.0623 (16)0.0433 (16)0.0222 (13)0.0060 (15)
C160.0466 (14)0.0656 (15)0.0845 (17)0.0269 (12)0.0177 (12)0.0100 (13)
C170.0474 (13)0.0511 (13)0.0893 (18)0.0233 (10)0.0036 (12)0.0119 (12)
C180.0529 (13)0.0420 (11)0.0567 (13)0.0244 (9)0.0025 (10)0.0069 (9)
C190.0431 (10)0.0406 (11)0.0415 (10)0.0148 (8)0.0046 (8)0.0045 (8)
Geometric parameters (Å, º) top
N1—C11.426 (2)C8—H8A0.99 (2)
N1—C71.409 (2)C9—C101.376 (4)
N1—C131.411 (2)C9—H9A0.95 (3)
O1—C191.299 (2)C10—C111.369 (4)
O1—H11.08 (4)C10—H10A1.00 (3)
O2—C191.227 (2)C11—C121.372 (3)
C1—C61.379 (2)C11—H11A0.98 (3)
C1—C21.398 (2)C12—H12A0.96 (2)
C2—C31.393 (3)C13—C141.378 (3)
C2—C191.482 (2)C13—C181.379 (3)
C3—C41.373 (3)C14—C151.377 (3)
C3—H3A0.96 (2)C14—H14A0.94 (3)
C4—C51.373 (3)C15—C161.363 (4)
C4—H4A0.94 (2)C15—H15A0.93 (3)
C5—C61.375 (3)C16—C171.366 (3)
C5—H5A0.96 (2)C16—H16A0.97 (2)
C7—C81.378 (3)C17—C181.382 (3)
C7—C121.391 (3)C17—H17A1.02 (2)
C6—H6A0.92 (2)C18—H18A0.97 (2)
C8—C91.380 (3)
C1—N1—C7118.01 (14)C11—C10—C9119.0 (2)
C1—N1—C13118.60 (14)C11—C10—H10A120.8 (17)
C7—N1—C13123.31 (15)C9—C10—H10A120.0 (17)
C19—O1—H1105.8 (16)C10—C11—C12121.0 (3)
C6—C1—C2119.00 (18)C10—C11—H11A119.7 (16)
C6—C1—N1117.93 (17)C12—C11—H11A119.3 (16)
C2—C1—N1123.05 (15)C11—C12—C7120.5 (2)
C3—C2—C1118.68 (16)C11—C12—H12A123.1 (14)
C3—C2—C19118.57 (17)C7—C12—H12A116.4 (14)
C1—C2—C19122.69 (17)C14—C13—C18117.95 (19)
C4—C3—C2121.4 (2)C14—C13—N1121.39 (17)
C4—C3—H3A123.3 (13)C18—C13—N1120.66 (17)
C2—C3—H3A115.0 (13)C15—C14—C13121.1 (2)
C3—C4—C5119.4 (2)C15—C14—H14A123.2 (15)
C3—C4—H4A119.7 (12)C13—C14—H14A115.7 (15)
C5—C4—H4A120.8 (12)C16—C15—C14120.6 (2)
C4—C5—C6120.1 (2)C16—C15—H15A120.4 (17)
C4—C5—H5A119.6 (14)C14—C15—H15A119.0 (17)
C6—C5—H5A120.3 (14)C15—C16—C17119.0 (2)
C8—C7—C12118.23 (19)C15—C16—H16A119.5 (15)
C8—C7—N1120.16 (17)C17—C16—H16A121.4 (15)
C12—C7—N1121.60 (18)C16—C17—C18120.8 (2)
C5—C6—C1121.3 (2)C16—C17—H17A117.6 (13)
C5—C6—H6A122.2 (14)C18—C17—H17A121.5 (13)
C1—C6—H6A116.5 (14)C13—C18—C17120.5 (2)
C7—C8—C9120.8 (2)C13—C18—H18A117.9 (13)
C7—C8—H8A118.9 (11)C17—C18—H18A121.6 (13)
C9—C8—H8A120.3 (11)O1—C19—C2114.72 (18)
C10—C9—C8120.4 (2)O2—C19—C2123.23 (18)
C10—C9—H9A122.8 (15)O1—C19—O2121.99 (18)
C8—C9—H9A116.8 (15)
C7—N1—C1—C664.0 (2)C9—C10—C11—C121.5 (4)
C13—N1—C1—C6112.8 (2)C10—C11—C12—C71.2 (4)
C7—N1—C1—C2117.85 (19)C8—C7—C12—C110.1 (3)
C6—C1—C2—C33.4 (3)N1—C7—C12—C11178.7 (2)
N1—C1—C2—C3174.76 (16)C7—N1—C13—C1431.8 (3)
C6—C1—C2—C19173.88 (18)C1—N1—C13—C14151.6 (2)
N1—C1—C2—C198.0 (3)C7—N1—C13—C18149.18 (18)
C1—C2—C3—C42.8 (3)C1—N1—C13—C1827.5 (2)
C19—C2—C3—C4174.55 (17)C18—C13—C14—C150.1 (4)
C2—C3—C4—C50.2 (3)N1—C13—C14—C15179.2 (2)
C3—C4—C5—C61.8 (3)C13—C14—C15—C161.0 (4)
C13—N1—C7—C8146.43 (17)C14—C15—C16—C170.6 (4)
C1—N1—C7—C836.9 (2)C15—C16—C17—C180.6 (4)
C13—N1—C7—C1234.8 (3)C14—C13—C18—C171.0 (3)
C1—N1—C7—C12141.88 (19)N1—C13—C18—C17178.00 (18)
C4—C5—C6—C11.2 (3)C16—C17—C18—C131.4 (3)
C2—C1—C6—C51.5 (3)C3—C2—C19—O2163.56 (19)
N1—C1—C6—C5176.79 (19)C1—C2—C19—O213.7 (3)
C12—C7—C8—C91.0 (3)C3—C2—C19—O113.6 (2)
N1—C7—C8—C9177.82 (17)C1—C2—C19—O1169.08 (18)
C7—C8—C9—C100.7 (3)C2—C1—N1—C1365.3 (2)
C8—C9—C10—C110.6 (4)O2—C19—O1—H13 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i1.08 (4)1.59 (4)2.657 (3)168 (3)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC19H15NO2
Mr289.32
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)9.145 (2), 9.427 (2), 9.889 (2)
α, β, γ (°)85.19 (3), 82.64 (3), 62.45 (3)
V3)749.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.5 × 0.3 × 0.3
Data collection
DiffractometerKuma KM-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4376, 4175, 1581
Rint0.036
(sin θ/λ)max1)0.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.151, 1.00
No. of reflections4175
No. of parameters259
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.18, 0.23

Computer programs: Kuma KM-4 Software (Kuma Diffraction, 1989), Kuma KM-4 Software, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top
N1—C11.426 (2)O1—C191.299 (2)
N1—C71.409 (2)O2—C191.227 (2)
N1—C131.411 (2)C2—C191.482 (2)
C1—N1—C7118.01 (14)O1—C19—C2114.72 (18)
C1—N1—C13118.60 (14)O2—C19—C2123.23 (18)
C7—N1—C13123.31 (15)O1—C19—O2121.99 (18)
C19—O1—H1105.8 (16)
C1—N1—C7—C836.9 (2)C2—C1—N1—C1365.3 (2)
C7—N1—C13—C1431.8 (3)O2—C19—O1—H13 (2)
C1—C2—C19—O213.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i1.08 (4)1.59 (4)2.657 (3)168 (3)
Symmetry code: (i) x+1, y+1, z+1.
Selected structural data for triphenylamino derivatives (Å, °) top
Compound nameSpace groupZAverage N—CAngle of inclinationbRef
distancea123
2-(N,N-Diphenylamino)benzoic acidP121.415 (3)64.535.829.2(i)
triphenylaminecB11b161.41839.741.449.4(ii)
38.244.650.5
40.341.548.0
37.044.449.8
Tri(4-methylphenyl)aminedP141.42130.733.061.2(iii)
31.336.758.2
Tri(2-methoxyphenyl)aminePa381.42244.444.444.4(iv)
Tri(2,3,4,5,6-pentachlorophenyl)amineA2/a41.42150.150.154.6(v)
Tri[4-(N-tert-butylamino-N-oxy)phenyl]amineCc41.42129.834.257.2(vi)
Notes: (a) average distance between the central N atom and the adjacent C atoms; (b) Angle between the average plane formed by the central N atom and the adjacent C atoms and the average plane formed by all C atoms of the benzene rings 1, 2 or 3; (c) sixteen molecules in the unit cell and four in the independent part of the unit cell; (d) four molecules in the unit cell and two in the independent part of the unit cell. References: (i) this work; (ii) Sobolev et al. (1985); (iii) Reynolds & Scaringe (1982); (iv) Müller & Bürgi (1989); (v) Hayes et al. (1980); (vi) Itoh et al. (1999).
 

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