N,N-Bis(4-meth-oxy-benzyl-idene)-3,3'-dimethyl-benzidine.

The mol-ecule of the title compund, C(30)H(28)N(2)O(2), a Schiff base synthesised via a condensation reaction between 4-meth-oxy-benzaldehyde and 3,3'-dimethyl-benzidine, a crystallographic twofold rotation axis passes through the mid-point of the C-C bond of the biphenyl unit. Thus, the asymmetric unit comprises one half-mol-ecule. In the biphenyl unit, the aromatic rings are twisted by 13.49 (7)° with respect to one another. The dihedral angles between the biphenyl and meth-oxy-benzene rings are 49.95 (12) and 50.06 (12)°. In the crystal, weak inter-molecular C-H⋯ O hydrogen bonds contribute to the stabilization of the packing.

Related literature

For the biological properties of Schiff base ligands, see: Bedia et al. (2006 ▶). For related structures, see: Harada et al. (2004 ▶); Nesterov (2004 ▶). For reference bond-length values, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C30H28N2O2

M = 448.54

Monoclinic,

a = 11.644 (2) Å

b = 16.228 (3) Å

c = 12.431 (3) Å

β = 91.75 (3)°

V = 2347.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 93 K

0.38 × 0.34 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.703, T max = 0.786

11279 measured reflections

2667 independent reflections

2350 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.05

2667 reflections

210 parameters

All H-atom parameters refined

Δρmax = 0.40 e Å−3

Δρmin = −0.19 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811023749/kp2337sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023749/kp2337Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023749/kp2337Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C30H28N2O2	F(000) = 952
Mr = 448.54	Dx = 1.269 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9010 reflections
a = 11.644 (2) Å	θ = 3.0–27.5°
b = 16.228 (3) Å	µ = 0.08 mm−1
c = 12.431 (3) Å	T = 93 K
β = 91.75 (3)°	Block, yellow
V = 2347.9 (8) Å3	0.38 × 0.34 × 0.22 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2667 independent reflections
Radiation source: fine-focus sealed tube	2350 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR ;Higashi, 1995)	h = −15→15
Tmin = 0.703, Tmax = 0.786	k = −20→20
11279 measured reflections	l = −14→16

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	All H-atom parameters refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0658P)2 + 1.0766P] where P = (Fo2 + 2Fc2)/3
2667 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.19 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	Uiso*/Ueq
O1	0.14801 (6)	0.07986 (5)	1.08572 (5)	0.01981 (19)
N1	0.36979 (7)	0.15477 (5)	0.62842 (7)	0.0176 (2)
C1	0.20415 (11)	0.12644 (8)	1.16991 (9)	0.0262 (3)
H1A	0.2839 (14)	0.1056 (10)	1.1839 (12)	0.034 (4)*
H1C	0.2050 (14)	0.1847 (10)	1.1522 (12)	0.038 (4)*
H1B	0.1570 (13)	0.1177 (10)	1.2330 (12)	0.037 (4)*
C2	0.18777 (9)	0.08948 (6)	0.98408 (8)	0.0165 (2)
C3	0.28693 (9)	0.13363 (6)	0.96025 (8)	0.0183 (2)
H3A	0.3342 (12)	0.1589 (8)	1.0165 (11)	0.025 (3)*
C4	0.31999 (9)	0.13940 (6)	0.85410 (8)	0.0179 (2)
H4A	0.3903 (12)	0.1681 (8)	0.8377 (10)	0.022 (3)*
C5	0.25488 (8)	0.10280 (6)	0.77062 (8)	0.0163 (2)
C6	0.15643 (9)	0.05837 (6)	0.79627 (8)	0.0179 (2)
H6A	0.1119 (11)	0.0334 (8)	0.7388 (10)	0.021 (3)*
C7	0.12313 (9)	0.05104 (6)	0.90185 (8)	0.0179 (2)
H7A	0.0561 (12)	0.0194 (8)	0.9196 (10)	0.024 (3)*
C8	0.28718 (8)	0.10911 (6)	0.65788 (8)	0.0176 (2)
H8A	0.2396 (11)	0.0762 (8)	0.6043 (10)	0.020 (3)*
C9	0.40025 (8)	0.15379 (6)	0.51899 (8)	0.0162 (2)
C10	0.43005 (8)	0.22903 (6)	0.47132 (8)	0.0159 (2)
C11	0.46879 (8)	0.22851 (6)	0.36602 (8)	0.0165 (2)
H11A	0.4919 (11)	0.2820 (9)	0.3346 (10)	0.023 (3)*
C12	0.47841 (8)	0.15556 (6)	0.30593 (7)	0.0160 (2)
C13	0.44641 (9)	0.08169 (6)	0.35559 (8)	0.0180 (2)
H13A	0.4501 (11)	0.0292 (8)	0.3175 (10)	0.019 (3)*
C14	0.40833 (9)	0.08084 (6)	0.46040 (8)	0.0183 (2)
H14A	0.3897 (12)	0.0279 (8)	0.4927 (10)	0.024 (3)*
C15	0.41802 (9)	0.30788 (7)	0.53365 (8)	0.0199 (2)
H15C	0.3378 (12)	0.3186 (9)	0.5538 (11)	0.028 (3)*
H15B	0.4624 (13)	0.3043 (9)	0.6036 (12)	0.032 (4)*
H15A	0.4450 (12)	0.3550 (8)	0.4925 (11)	0.025 (3)*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (4)	0.0261 (4)	0.0126 (4)	−0.0009 (3)	0.0023 (3)	0.0020 (3)
N1	0.0179 (4)	0.0209 (4)	0.0141 (4)	0.0005 (3)	0.0020 (3)	0.0021 (3)
C1	0.0341 (6)	0.0295 (6)	0.0151 (5)	−0.0047 (5)	0.0020 (4)	−0.0012 (4)
C2	0.0178 (5)	0.0179 (5)	0.0140 (5)	0.0039 (4)	0.0024 (3)	0.0029 (4)
C3	0.0184 (5)	0.0198 (5)	0.0166 (5)	−0.0003 (4)	−0.0011 (4)	0.0006 (4)
C4	0.0163 (5)	0.0192 (5)	0.0181 (5)	−0.0012 (4)	0.0012 (4)	0.0023 (4)
C5	0.0166 (5)	0.0171 (5)	0.0153 (5)	0.0021 (4)	0.0018 (3)	0.0019 (4)
C6	0.0171 (5)	0.0201 (5)	0.0166 (5)	−0.0001 (4)	0.0005 (4)	−0.0009 (4)
C7	0.0160 (5)	0.0195 (5)	0.0185 (5)	−0.0010 (4)	0.0032 (4)	0.0010 (4)
C8	0.0168 (5)	0.0200 (5)	0.0160 (5)	0.0009 (4)	0.0003 (4)	0.0014 (4)
C9	0.0130 (4)	0.0224 (5)	0.0132 (5)	−0.0003 (4)	0.0003 (3)	0.0011 (4)
C10	0.0129 (4)	0.0197 (5)	0.0150 (5)	−0.0008 (3)	0.0000 (3)	−0.0005 (4)
C11	0.0161 (5)	0.0184 (5)	0.0152 (5)	−0.0007 (4)	0.0008 (3)	0.0015 (4)
C12	0.0151 (5)	0.0191 (5)	0.0138 (5)	0.0002 (3)	0.0003 (4)	0.0004 (4)
C13	0.0195 (5)	0.0179 (5)	0.0167 (5)	−0.0003 (4)	0.0009 (4)	−0.0012 (4)
C14	0.0186 (5)	0.0187 (5)	0.0176 (5)	−0.0014 (4)	0.0016 (4)	0.0032 (4)
C15	0.0223 (5)	0.0203 (5)	0.0172 (5)	−0.0017 (4)	0.0040 (4)	−0.0021 (4)

O1—C2	1.3677 (12)	C7—H7A	0.965 (14)
O1—C1	1.4325 (14)	C8—H8A	1.006 (13)
N1—C8	1.2767 (13)	C9—C14	1.3946 (15)
N1—C9	1.4164 (12)	C9—C10	1.4054 (14)
C1—H1A	0.999 (16)	C10—C11	1.3976 (14)
C1—H1C	0.972 (17)	C10—C15	1.5046 (14)
C1—H1B	0.981 (15)	C11—C12	1.4061 (14)
C2—C7	1.3978 (15)	C11—H11A	0.992 (14)
C2—C3	1.3982 (14)	C12—C13	1.4039 (14)
C3—C4	1.3891 (14)	C12—C12i	1.4930 (18)
C3—H3A	0.968 (14)	C13—C14	1.3892 (14)
C4—C5	1.3987 (15)	C13—H13A	0.975 (13)
C4—H4A	0.969 (14)	C14—H14A	0.976 (13)
C5—C6	1.3993 (14)	C15—H15C	0.990 (14)
C5—C8	1.4657 (13)	C15—H15B	1.000 (15)
C6—C7	1.3851 (14)	C15—H15A	0.977 (14)
C6—H6A	0.960 (13)
C2—O1—C1	117.07 (8)	N1—C8—H8A	121.5 (7)
C8—N1—C9	118.82 (9)	C5—C8—H8A	116.3 (7)
O1—C1—H1A	110.5 (9)	C14—C9—C10	119.73 (9)
O1—C1—H1C	110.8 (9)	C14—C9—N1	122.27 (9)
H1A—C1—H1C	110.7 (13)	C10—C9—N1	117.87 (9)
O1—C1—H1B	104.7 (9)	C11—C10—C9	118.72 (9)
H1A—C1—H1B	110.6 (12)	C11—C10—C15	121.69 (9)
H1C—C1—H1B	109.4 (13)	C9—C10—C15	119.58 (9)
O1—C2—C7	115.77 (9)	C10—C11—C12	122.41 (9)
O1—C2—C3	124.00 (9)	C10—C11—H11A	117.6 (7)
C7—C2—C3	120.23 (9)	C12—C11—H11A	120.0 (7)
C4—C3—C2	119.37 (10)	C13—C12—C11	117.30 (9)
C4—C3—H3A	119.3 (8)	C13—C12—C12i	120.73 (6)
C2—C3—H3A	121.3 (8)	C11—C12—C12i	121.96 (6)
C3—C4—C5	121.10 (9)	C14—C13—C12	121.17 (9)
C3—C4—H4A	119.5 (8)	C14—C13—H13A	117.8 (7)
C5—C4—H4A	119.4 (8)	C12—C13—H13A	121.1 (7)
C4—C5—C6	118.62 (9)	C13—C14—C9	120.66 (9)
C4—C5—C8	122.06 (9)	C13—C14—H14A	118.4 (7)
C6—C5—C8	119.33 (9)	C9—C14—H14A	120.9 (7)
C7—C6—C5	121.02 (10)	C10—C15—H15C	112.6 (8)
C7—C6—H6A	120.6 (8)	C10—C15—H15B	110.1 (9)
C5—C6—H6A	118.4 (8)	H15C—C15—H15B	104.9 (11)
C6—C7—C2	119.64 (9)	C10—C15—H15A	111.0 (8)
C6—C7—H7A	120.9 (8)	H15C—C15—H15A	108.4 (11)
C2—C7—H7A	119.4 (8)	H15B—C15—H15A	109.6 (12)
N1—C8—C5	122.17 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O1ii	0.960 (13)	2.688 (13)	3.4462 (15)	136.32

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O1i	0.960 (13)	2.688 (13)	3.4462 (15)	136.32 (su?)

Symmetry code: (i) .