1,8-Bis(4-amino-benzo-yl)-2,7-dimeth-oxy-naphthalene.

The title compound {systematic name: [8-(4-aminobenzoyl)-2,7-dimethoxynaphthalen-1-yl](4-aminophenyl)methanone}, C(26)H(22)O(4)N(2), possesses crystallographically imposed twofold symmetry, with two C atoms lying on the rotation axis. In the crystal, the mol-ecules inter-act through inter-molecular N-H⋯O hydrogen bonds between the amino and meth-oxy groups on the naphthalene ring systems and N-H⋯π inter-actions between the amino groups and the naphthalene rings. Furthermore, weak C-H⋯O hydrogen bonds and π-π stacking inter-actions between the benzene rings are observed. The centroid-centroid and inter-planar distances between the benzene rings of the aroyl group and the naphthalene ring systems of adjacent mol-ecules are 3.6954 (8) and 3.2375 (5) Å, respectively. The dihedral angle between the mean planes of the benzene ring and the naphthalene ring system is 83.59 (5)°. The benzene ring and the carbonyl group in the benzoyl unit are almost coplanar [C-C-C-O torsion angle = 175.91 (10)°].

Related literature

For the formation reaction of aroylated naphthalene compounds via electrophilic aromatic aroylation of 2,7-dimeth­oxy­naphthalene, see: Okamoto & Yonezawa (2009 ▶). For related structures, see: Muto et al. (2010 ▶); Nakaema et al. (2007 ▶, 2008 ▶); Watanabe et al. (2010a ▶,b ▶). For work-up procedure in the preparation of the title compound, see: Bellamy et al. (1984 ▶).

Experimental

Crystal data

C26H22N2O4

M = 426.46

Monoclinic,

a = 14.2996 (3) Å

b = 10.2811 (2) Å

c = 15.4306 (3) Å

β = 114.523 (1)°

V = 2063.90 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.76 mm−1

T = 193 K

0.40 × 0.30 × 0.10 mm

Data collection

Rigaki R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.751, T max = 0.928

17453 measured reflections

1892 independent reflections

1690 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.114

S = 1.12

1892 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.37 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810041346/rz2496sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041346/rz2496Isup2.hkl

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

C26H22N2O4	F(000) = 896
Mr = 426.46	Dx = 1.372 Mg m−3
Monoclinic, C2/c	Melting point = 580.5–583.0 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54187 Å
a = 14.2996 (3) Å	Cell parameters from 11162 reflections
b = 10.2811 (2) Å	θ = 3.1–68.2°
c = 15.4306 (3) Å	µ = 0.76 mm−1
β = 114.523 (1)°	T = 193 K
V = 2063.90 (7) Å3	Platelet, brown
Z = 4	0.40 × 0.30 × 0.10 mm

Rigaki R-AXIS RAPID diffractometer	1892 independent reflections
Radiation source: rotating anode	1690 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 5.5°
ω scans	h = −17→17
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.751, Tmax = 0.928	l = −18→18
17453 measured reflections

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) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.6125P] where P = (Fo2 + 2Fc2)/3
1892 reflections	(Δ/σ)max = 0.001
178 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.37 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	0.77436 (7)	−0.11857 (9)	0.88398 (7)	0.0426 (3)
O2	0.62425 (7)	0.07379 (8)	0.72735 (6)	0.0341 (3)
N1	0.63099 (9)	0.33681 (13)	1.10437 (8)	0.0405 (3)
C1	0.62489 (9)	0.26028 (13)	1.02908 (8)	0.0307 (3)
C2	0.63071 (9)	0.31736 (12)	0.94876 (9)	0.0311 (3)
C3	0.62524 (9)	0.24184 (12)	0.87347 (8)	0.0293 (3)
C4	0.61301 (8)	0.10665 (11)	0.87440 (8)	0.0268 (3)
C5	0.60412 (9)	0.05115 (13)	0.95329 (9)	0.0311 (3)
C6	0.60986 (9)	0.12582 (13)	1.02970 (9)	0.0333 (3)
C7	0.61101 (8)	0.02784 (12)	0.79446 (8)	0.0266 (3)
C8	0.59675 (9)	−0.11834 (12)	0.79669 (8)	0.0278 (3)
C9	0.5000	−0.18296 (16)	0.7500	0.0267 (4)
C10	0.5000	−0.32223 (16)	0.7500	0.0302 (4)
C11	0.59352 (11)	−0.39011 (13)	0.79714 (9)	0.0355 (3)
C12	0.68471 (11)	−0.32756 (13)	0.84270 (9)	0.0366 (3)
C13	0.68596 (9)	−0.19016 (13)	0.84184 (9)	0.0328 (3)
C14	0.86976 (11)	−0.18638 (16)	0.93136 (11)	0.0495 (4)
H14A	0.9248	−0.1246	0.9574	0.059*
H14B	0.8815	−0.2415	0.8866	0.059*
H14C	0.8669	−0.2385	0.9818	0.059*
H1	0.5936 (11)	−0.0400 (16)	0.9542 (10)	0.038 (4)*
H2	0.6079 (12)	0.0862 (14)	1.0838 (11)	0.039 (4)*
H3	0.6425 (15)	0.2952 (19)	1.1606 (14)	0.068 (6)*
H4	0.6672 (15)	0.413 (2)	1.1123 (13)	0.065 (5)*
H5	0.6425 (11)	0.4089 (16)	0.9514 (10)	0.038 (4)*
H6	0.6305 (11)	0.2772 (14)	0.8178 (10)	0.034 (3)*
H7	0.5900 (12)	−0.4824 (17)	0.7944 (11)	0.047 (4)*
H8	0.7479 (13)	−0.3756 (16)	0.8739 (11)	0.048 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0267 (5)	0.0363 (6)	0.0529 (6)	0.0065 (4)	0.0048 (4)	0.0005 (4)
O2	0.0404 (5)	0.0317 (5)	0.0299 (5)	−0.0019 (4)	0.0141 (4)	0.0015 (4)
N1	0.0409 (7)	0.0464 (7)	0.0354 (6)	−0.0038 (6)	0.0170 (5)	−0.0089 (5)
C1	0.0217 (6)	0.0375 (7)	0.0311 (6)	0.0004 (5)	0.0091 (5)	−0.0033 (5)
C2	0.0309 (6)	0.0258 (7)	0.0348 (7)	−0.0006 (5)	0.0117 (5)	−0.0005 (5)
C3	0.0289 (6)	0.0275 (7)	0.0298 (6)	0.0001 (5)	0.0106 (5)	0.0034 (5)
C4	0.0221 (6)	0.0258 (6)	0.0291 (6)	0.0002 (4)	0.0074 (4)	0.0010 (4)
C5	0.0296 (6)	0.0279 (7)	0.0350 (7)	−0.0015 (5)	0.0126 (5)	0.0032 (5)
C6	0.0321 (6)	0.0383 (7)	0.0308 (6)	−0.0010 (5)	0.0144 (5)	0.0039 (5)
C7	0.0198 (5)	0.0271 (6)	0.0281 (6)	0.0002 (4)	0.0053 (4)	0.0016 (4)
C8	0.0305 (6)	0.0259 (7)	0.0271 (6)	0.0023 (5)	0.0120 (5)	0.0006 (4)
C9	0.0329 (9)	0.0249 (9)	0.0241 (8)	0.000	0.0136 (7)	0.000
C10	0.0407 (10)	0.0258 (9)	0.0278 (8)	0.000	0.0180 (7)	0.000
C11	0.0520 (8)	0.0235 (7)	0.0332 (7)	0.0058 (5)	0.0200 (6)	0.0030 (5)
C12	0.0408 (8)	0.0318 (7)	0.0350 (7)	0.0124 (6)	0.0135 (6)	0.0053 (5)
C13	0.0319 (7)	0.0319 (7)	0.0321 (6)	0.0033 (5)	0.0108 (5)	0.0004 (5)
C14	0.0308 (7)	0.0487 (9)	0.0550 (9)	0.0133 (6)	0.0040 (6)	−0.0041 (7)

O1—C13	1.3712 (15)	C6—H2	0.939 (15)
O1—C14	1.4331 (15)	C7—C8	1.5189 (17)
O2—C7	1.2223 (14)	C8—C13	1.3857 (17)
N1—C1	1.3756 (16)	C8—C9	1.4308 (14)
N1—H3	0.92 (2)	C9—C8i	1.4308 (14)
N1—H4	0.92 (2)	C9—C10	1.432 (2)
C1—C6	1.3996 (19)	C10—C11i	1.4132 (16)
C1—C2	1.4045 (17)	C10—C11	1.4132 (16)
C2—C3	1.3724 (17)	C11—C12	1.359 (2)
C2—H5	0.954 (16)	C11—H7	0.950 (18)
C3—C4	1.4017 (17)	C12—C13	1.4128 (19)
C3—H6	0.964 (14)	C12—H8	0.965 (17)
C4—C5	1.3972 (16)	C14—H14A	0.9600
C4—C7	1.4662 (16)	C14—H14B	0.9600
C5—C6	1.3806 (18)	C14—H14C	0.9600
C5—H1	0.950 (16)
C13—O1—C14	118.41 (11)	C13—C8—C9	120.11 (12)
C1—N1—H3	117.1 (12)	C13—C8—C7	115.75 (10)
C1—N1—H4	115.9 (12)	C9—C8—C7	123.98 (11)
H3—N1—H4	113.7 (17)	C8—C9—C8i	124.66 (15)
N1—C1—C6	121.01 (12)	C8—C9—C10	117.67 (8)
N1—C1—C2	120.00 (12)	C8i—C9—C10	117.67 (8)
C6—C1—C2	118.97 (11)	C11i—C10—C11	120.81 (17)
C3—C2—C1	120.48 (12)	C11i—C10—C9	119.59 (8)
C3—C2—H5	122.7 (8)	C11—C10—C9	119.59 (8)
C1—C2—H5	116.7 (8)	C12—C11—C10	122.17 (13)
C2—C3—C4	121.05 (11)	C12—C11—H7	121.2 (9)
C2—C3—H6	122.9 (9)	C10—C11—H7	116.6 (10)
C4—C3—H6	116.1 (9)	C11—C12—C13	118.78 (12)
C5—C4—C3	118.09 (11)	C11—C12—H8	121.0 (10)
C5—C4—C7	122.03 (11)	C13—C12—H8	120.2 (10)
C3—C4—C7	119.88 (11)	O1—C13—C8	115.30 (11)
C6—C5—C4	121.49 (12)	O1—C13—C12	123.02 (11)
C6—C5—H1	119.3 (9)	C8—C13—C12	121.67 (12)
C4—C5—H1	119.2 (9)	O1—C14—H14A	109.5
C5—C6—C1	119.88 (11)	O1—C14—H14B	109.5
C5—C6—H2	120.3 (9)	H14A—C14—H14B	109.5
C1—C6—H2	119.7 (9)	O1—C14—H14C	109.5
O2—C7—C4	122.92 (11)	H14A—C14—H14C	109.5
O2—C7—C8	118.10 (10)	H14B—C14—H14C	109.5
C4—C7—C8	118.92 (10)
N1—C1—C2—C3	179.66 (11)	C7—C8—C9—C8i	−6.37 (8)
C6—C1—C2—C3	−2.20 (18)	C13—C8—C9—C10	−1.54 (11)
C1—C2—C3—C4	0.48 (18)	C7—C8—C9—C10	173.63 (8)
C2—C3—C4—C5	1.46 (17)	C8—C9—C10—C11i	−178.56 (8)
C2—C3—C4—C7	−177.87 (10)	C8i—C9—C10—C11i	1.44 (8)
C3—C4—C5—C6	−1.70 (17)	C8—C9—C10—C11	1.44 (8)
C7—C4—C5—C6	177.61 (10)	C8i—C9—C10—C11	−178.56 (8)
C4—C5—C6—C1	0.00 (18)	C11i—C10—C11—C12	179.69 (13)
N1—C1—C6—C5	−179.93 (11)	C9—C10—C11—C12	−0.31 (13)
C2—C1—C6—C5	1.96 (18)	C10—C11—C12—C13	−0.74 (18)
C5—C4—C7—O2	−175.91 (10)	C14—O1—C13—C8	−179.48 (11)
C3—C4—C7—O2	3.40 (17)	C14—O1—C13—C12	−0.25 (18)
C5—C4—C7—C8	1.21 (16)	C9—C8—C13—O1	179.77 (9)
C3—C4—C7—C8	−179.48 (10)	C7—C8—C13—O1	4.22 (15)
O2—C7—C8—C13	89.52 (13)	C9—C8—C13—C12	0.53 (17)
C4—C7—C8—C13	−87.74 (13)	C7—C8—C13—C12	−175.03 (11)
O2—C7—C8—C9	−85.85 (13)	C11—C12—C13—O1	−178.55 (11)
C4—C7—C8—C9	96.90 (12)	C11—C12—C13—C8	0.64 (19)
C13—C8—C9—C8i	178.46 (11)

Cg is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H4···O1ii	0.93 (2)	2.26 (2)	3.1708 (17)	169.1 (18)
C14—H14B···O2iii	0.96	2.57	3.5013 (18)	165
N1—H3···Cgiv	0.92 (2)	2.50 (2)	3.3301 (13)	149.8 (18)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H4⋯O1i	0.93 (2)	2.26 (2)	3.1708 (17)	169.1 (18)
C14—H14B⋯O2ii	0.96	2.57	3.5013 (18)	165
N1—H3⋯Cgiii	0.92 (2)	2.50 (2)	3.3301 (13)	149.8 (18)

Symmetry codes: (i) ; (ii) ; (iii) .