N,N'-Bis(di-phenyl-meth-yl)benzene-1,4-di-amine.

The complete mol-ecule of the title compound, C32H28N2, is generated by crystallographic inversion symmetry. The dihedral angles between the central aromatic ring and the pendant adjacent rings are 61.37 (16) and 74.20 (14)°. The N-H group does not participate in hydrogen bonds and there are no aromatic π-π stacking inter-actions in the crystal.

Related literature

The reduction of the Schiff-base was as described in Higuchi et al. (2003 ▶) and Higuchi et al. (2000 ▶). For the use of dendrimers in the formation of new types of organic-metallic hybrid materials, see: Kim et al. (2005 ▶); for drug generation, see: Basavaraj et al. (2009 ▶). For related structures, see: Ge & Ng (2006 ▶); Yang et al. (2007 ▶); Xia et al. (2007 ▶). Data were collected and processed according to Coles & Gale (2012 ▶).

Experimental

Crystal data

C32H28N2

M = 440.56

Monoclinic,

a = 14.784 (2) Å

b = 5.5853 (8) Å

c = 14.896 (2) Å

β = 107.914 (8)°

V = 1170.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.1 × 0.09 × 0.02 mm

Data collection

Rigaku AFC12 (Right) diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▶) T min = 0.345, T max = 1.000

10305 measured reflections

2664 independent reflections

1254 reflections with I > 2σ(I)

R int = 0.125

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.208

S = 0.97

2664 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXD (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813033497/hb7158sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033497/hb7158Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033497/hb7158Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033497/hb7158Isup4.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C32H28N2	F(000) = 468
Mr = 440.56	Dx = 1.250 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
a = 14.784 (2) Å	Cell parameters from 5636 reflections
b = 5.5853 (8) Å	θ = 3.4–27.5°
c = 14.896 (2) Å	µ = 0.07 mm−1
β = 107.914 (8)°	T = 100 K
V = 1170.4 (3) Å3	Plate, colourless
Z = 2	0.1 × 0.09 × 0.02 mm

Rigaku AFC12 (Right) diffractometer	2664 independent reflections
Radiation source: Rotating Anode	1254 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.125
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.4°
profile data from ω–scans	h = −19→18
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	k = −7→6
Tmin = 0.345, Tmax = 1.000	l = −16→19
10305 measured reflections

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)] = 0.077	H-atom parameters constrained
wR(F2) = 0.208	w = 1/[σ2(Fo2) + (0.0886P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
2664 reflections	Δρmax = 0.33 e Å−3
155 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: dual	Extinction coefficient: 0.026 (5)

Experimental. FT—IR data were recorded on a Nicolet ATR FT—IR, while NMR data were collected on a Bruker 400 MHz s pectrometer in CD2Cl2– d2 solutions. The assignment of the chemical shifts for the NMR data were made following numbering shown in structure B. Schiff-base {N1,N4-bis(diphenylmethylene)benzene-1,4-diamine}IR (ATR cm-1) 1620 (C=N), 1597 and 1570 (phenyl). NMR data (p.p.m.), δH (400 MHz, CD2Cl2): 6.47 (4H, m; C3, 3`, 11, 11`-H), 7.06 (2H, d, J = 7.33 Hz; C15, 15`-H), 7.73 (2H, d, J = 7.33 Hz; C16, 16`-H), 7.27–7.40 (20H, m; aromatic-H); δC (100.63 MHz, CD2Cl2): 121.53–136.75, (aromatic carbon); 140.12 (C6, 6`,8, 8`); 147.37 (C14, 14`); 168.24 (C7, 7`); DEPT 13 C NMR exhibited no signals between 140–170 p.p.m.. The positive ES mass spectrum of the bis-amine showed the parent ion peak at m/z = 441.2362 (M+H)+ (95%) corresponding to C32H28N2; required value = 440.2252. Peaks detected at m/z =247.16 (100%) and 167.09 (98%), correspond to [M-(ph)2CH2)]+ and [M-(ph)2CH2+H2N2ph)]+, respectively.bis-amine {N1,N4-dibenzhydrylbenzene-1,4-diamine IR (ATR cm-1): 3392 (N—H), 2932; 2873 (C—H) aliphatic, 1599 and 1510 (phenyl). NMR data (p.p.m.), δH (400 MHz, CD2Cl2): 3.95 (2H, S, Na, a`-H), 5.36 (2H, S; C7, 7`-H), 6.37 (4H, d, J=7.33 Hz; C15, 15`, 16, 16`-H), 7.21–7.36 (20H, m, Ar—H); δC (100.63 MHz, CD2Cl2): 49.10 (C7, 7`); 115.21 (C15, 15`, 16, 16`); 127.25–129.04 (aromatic carbon); 140 (C6, 6`, 8, 8`); 144.07 (C14, 14`), DEPT 13 C NMR exhibited no signals between 140–145 p.p.m.. The positive ES mass spectrum of the bis-amine showed the parent ion peak at m/z = 441.2362 (M+H)+ (95%) corresponding to C32H28N2; required value = 440.2252. Peaks detected at m/z =247.16 (100%) and 167.09 (98%), correspond to [M-(ph)2CH2)]+ and [M-(ph)2CH2+H2N2ph)]+, respectively.

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	Uiso*/Ueq
N1	0.44891 (16)	0.4954 (4)	0.1672 (2)	0.0366 (7)
H1	0.4144	0.6110	0.1765	0.044*
C2	0.47809 (19)	0.3103 (5)	0.2375 (2)	0.0294 (8)
H2	0.4635	0.1559	0.2050	0.035*
C3	0.58440 (19)	0.3135 (5)	0.2909 (2)	0.0273 (7)
C4	0.6426 (2)	0.5024 (5)	0.2829 (2)	0.0295 (8)
H4	0.6169	0.6316	0.2440	0.035*
C5	0.7386 (2)	0.4993 (5)	0.3323 (2)	0.0314 (8)
H5	0.7768	0.6270	0.3265	0.038*
C6	0.7785 (2)	0.3094 (5)	0.3901 (2)	0.0326 (8)
H6	0.8431	0.3080	0.4231	0.039*
C7	0.7208 (2)	0.1209 (5)	0.3983 (2)	0.0329 (8)
H7	0.7468	−0.0081	0.4371	0.039*
C8	0.6248 (2)	0.1228 (5)	0.3492 (2)	0.0325 (8)
H8	0.5868	−0.0051	0.3554	0.039*
C9	0.41899 (19)	0.3290 (5)	0.3050 (2)	0.0303 (8)
C10	0.4294 (2)	0.5250 (5)	0.3644 (3)	0.0392 (9)
H10	0.4723	0.6451	0.3626	0.047*
C11	0.3771 (2)	0.5438 (6)	0.4259 (3)	0.0433 (9)
H11	0.3845	0.6767	0.4651	0.052*
C12	0.3137 (2)	0.3662 (6)	0.4296 (3)	0.0416 (9)
H12	0.2782	0.3785	0.4712	0.050*
C13	0.3032 (2)	0.1706 (6)	0.3712 (3)	0.0421 (10)
H13	0.2614	0.0487	0.3742	0.051*
C14	0.3545 (2)	0.1546 (5)	0.3081 (3)	0.0386 (9)
H14	0.3454	0.0245	0.2673	0.046*
C15	0.47494 (18)	0.4941 (5)	0.0834 (2)	0.0283 (8)
C16	0.5290 (2)	0.3109 (5)	0.0627 (2)	0.0315 (8)
H16	0.5489	0.1834	0.1042	0.038*
C17	0.44676 (19)	0.6813 (5)	0.0199 (2)	0.0294 (8)
H17	0.4107	0.8049	0.0332	0.035*

	U11	U22	U33	U12	U13	U23
N1	0.0298 (14)	0.0449 (16)	0.039 (2)	0.0124 (13)	0.0167 (14)	0.0079 (14)
C2	0.0222 (15)	0.0330 (16)	0.032 (2)	0.0024 (13)	0.0070 (14)	−0.0015 (14)
C3	0.0212 (14)	0.0322 (16)	0.030 (2)	−0.0007 (13)	0.0109 (14)	−0.0032 (14)
C4	0.0244 (15)	0.0290 (15)	0.035 (2)	0.0028 (13)	0.0094 (14)	0.0020 (14)
C5	0.0255 (15)	0.0340 (17)	0.035 (2)	−0.0023 (14)	0.0094 (15)	−0.0016 (15)
C6	0.0218 (15)	0.0415 (18)	0.034 (2)	0.0026 (14)	0.0076 (15)	−0.0063 (15)
C7	0.0279 (16)	0.0329 (17)	0.039 (2)	0.0084 (14)	0.0125 (16)	0.0026 (15)
C8	0.0257 (16)	0.0318 (17)	0.042 (2)	0.0006 (13)	0.0137 (16)	0.0046 (15)
C9	0.0210 (14)	0.0349 (17)	0.035 (2)	0.0010 (14)	0.0089 (14)	0.0025 (15)
C10	0.0319 (17)	0.0354 (18)	0.053 (3)	−0.0069 (15)	0.0177 (18)	−0.0066 (17)
C11	0.0378 (19)	0.047 (2)	0.048 (3)	0.0018 (17)	0.0177 (18)	−0.0068 (18)
C12	0.0345 (18)	0.050 (2)	0.048 (3)	0.0093 (17)	0.0248 (18)	0.0082 (18)
C13	0.0324 (18)	0.049 (2)	0.053 (3)	−0.0051 (16)	0.0253 (18)	0.0042 (18)
C14	0.0308 (17)	0.0357 (17)	0.053 (3)	−0.0058 (15)	0.0187 (17)	−0.0035 (16)
C15	0.0156 (13)	0.0345 (16)	0.032 (2)	−0.0022 (13)	0.0039 (14)	−0.0001 (15)
C16	0.0219 (14)	0.0351 (17)	0.037 (2)	0.0020 (13)	0.0086 (14)	0.0049 (15)
C17	0.0182 (14)	0.0350 (17)	0.036 (2)	0.0025 (13)	0.0106 (14)	−0.0022 (15)

N1—H1	0.8600	C9—C10	1.386 (4)
N1—C2	1.440 (4)	C9—C14	1.373 (4)
N1—C15	1.415 (4)	C10—H10	0.9300
C2—H2	0.9800	C10—C11	1.372 (4)
C2—C3	1.528 (4)	C11—H11	0.9300
C2—C9	1.525 (4)	C11—C12	1.378 (4)
C3—C4	1.389 (4)	C12—H12	0.9300
C3—C8	1.388 (4)	C12—C13	1.375 (5)
C4—H4	0.9300	C13—H13	0.9300
C4—C5	1.384 (4)	C13—C14	1.380 (4)
C5—H5	0.9300	C14—H14	0.9300
C5—C6	1.379 (4)	C15—C16	1.391 (4)
C6—H6	0.9300	C15—C17	1.385 (4)
C6—C7	1.384 (4)	C16—H16	0.9300
C7—H7	0.9300	C16—C17i	1.384 (4)
C7—C8	1.382 (4)	C17—C16i	1.384 (4)
C8—H8	0.9300	C17—H17	0.9300
C2—N1—H1	118.8	C10—C9—C2	120.1 (2)
C15—N1—H1	118.8	C14—C9—C2	121.2 (3)
C15—N1—C2	122.4 (2)	C14—C9—C10	118.7 (3)
N1—C2—H2	107.6	C9—C10—H10	119.6
N1—C2—C3	113.6 (2)	C11—C10—C9	120.8 (3)
N1—C2—C9	109.0 (2)	C11—C10—H10	119.6
C3—C2—H2	107.6	C10—C11—H11	120.0
C9—C2—H2	107.6	C10—C11—C12	120.1 (3)
C9—C2—C3	111.2 (3)	C12—C11—H11	120.0
C4—C3—C2	121.9 (3)	C11—C12—H12	120.3
C8—C3—C2	119.5 (2)	C13—C12—C11	119.5 (3)
C8—C3—C4	118.6 (3)	C13—C12—H12	120.3
C3—C4—H4	119.8	C12—C13—H13	119.9
C5—C4—C3	120.4 (3)	C12—C13—C14	120.3 (3)
C5—C4—H4	119.8	C14—C13—H13	119.9
C4—C5—H5	119.6	C9—C14—C13	120.6 (3)
C6—C5—C4	120.9 (3)	C9—C14—H14	119.7
C6—C5—H5	119.6	C13—C14—H14	119.7
C5—C6—H6	120.6	C16—C15—N1	122.1 (3)
C5—C6—C7	118.9 (3)	C17—C15—N1	119.5 (3)
C7—C6—H6	120.6	C17—C15—C16	118.5 (3)
C6—C7—H7	119.7	C15—C16—H16	120.1
C8—C7—C6	120.6 (3)	C17i—C16—C15	119.9 (3)
C8—C7—H7	119.7	C17i—C16—H16	120.1
C3—C8—H8	119.7	C15—C17—H17	119.2
C7—C8—C3	120.7 (3)	C16i—C17—C15	121.7 (3)
C7—C8—H8	119.7	C16i—C17—H17	119.2
N1—C2—C3—C4	10.4 (4)	C4—C5—C6—C7	−0.2 (5)
N1—C2—C3—C8	−169.4 (3)	C5—C6—C7—C8	0.1 (4)
N1—C2—C9—C10	−67.2 (4)	C6—C7—C8—C3	0.0 (5)
N1—C2—C9—C14	112.5 (3)	C8—C3—C4—C5	−0.1 (4)
N1—C15—C16—C17i	−179.5 (3)	C9—C2—C3—C4	−113.0 (3)
N1—C15—C17—C16i	179.5 (3)	C9—C2—C3—C8	67.2 (3)
C2—N1—C15—C16	1.3 (4)	C9—C10—C11—C12	0.4 (5)
C2—N1—C15—C17	−178.1 (3)	C10—C9—C14—C13	−1.9 (5)
C2—C3—C4—C5	−180.0 (3)	C10—C11—C12—C13	0.0 (5)
C2—C3—C8—C7	179.9 (3)	C11—C12—C13—C14	−1.3 (5)
C2—C9—C10—C11	−179.7 (3)	C12—C13—C14—C9	2.3 (5)
C2—C9—C14—C13	178.4 (3)	C14—C9—C10—C11	0.6 (5)
C3—C2—C9—C10	58.8 (4)	C15—N1—C2—C3	69.6 (3)
C3—C2—C9—C14	−121.5 (3)	C15—N1—C2—C9	−165.8 (2)
C3—C4—C5—C6	0.2 (5)	C16—C15—C17—C16i	0.1 (5)
C4—C3—C8—C7	0.1 (4)	C17—C15—C16—C17i	−0.1 (4)